 
data_4pzH-F2
  
_audit_creation_method            'SHELXL-2018/3' 
_shelx_SHELXL_version_number      '2018/3' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 'C10 H8 F2 N4' 
_chemical_formula_sum 
 'C10 H8 F2 N4' 
_chemical_formula_weight          222.20 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'F'  'F'   0.0171   0.0103 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/c' 
_space_group_name_Hall            '-P 2ybc' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
  
_cell_length_a                    19.826(3) 
_cell_length_b                    3.9279(4) 
_cell_length_c                    13.2624(17) 
_cell_angle_alpha                 90 
_cell_angle_beta                  109.525(15) 
_cell_angle_gamma                 90 
_cell_volume                      973.4(2) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     2009 
_cell_measurement_theta_min       3.2120 
_cell_measurement_theta_max       27.3420 
  
_exptl_crystal_description        'tabular needles' 
_exptl_crystal_colour             Yellow 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.516 
_exptl_crystal_F_000              456 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.502 
_exptl_crystal_size_mid           0.467 
_exptl_crystal_size_min           0.080 
_exptl_absorpt_coefficient_mu     0.124 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.948 
_exptl_absorpt_correction_T_max   0.990 
_exptl_absorpt_process_details     
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
; 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    'Enhance (Mo) X-ray Source' 
_diffrn_measurement_device_type   'Agilent Xcalibur 3 E' 
_diffrn_measurement_method        'omega scans' 
_diffrn_detector_area_resol_mean  16.0382 
_diffrn_reflns_number             5165 
_diffrn_reflns_av_unetI/netI      0.0297 
_diffrn_reflns_av_R_equivalents   0.0207 
_diffrn_reflns_limit_h_min        -25 
_diffrn_reflns_limit_h_max        16 
_diffrn_reflns_limit_k_min        -4 
_diffrn_reflns_limit_k_max        4 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          3.072 
_diffrn_reflns_theta_max          28.063 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.860 
_diffrn_measured_fraction_theta_full  0.998 
_diffrn_reflns_Laue_measured_fraction_max    0.860 
_diffrn_reflns_Laue_measured_fraction_full   0.998 
_diffrn_reflns_point_group_measured_fraction_max   0.860 
_diffrn_reflns_point_group_measured_fraction_full  0.998 
_reflns_number_total              2044 
_reflns_number_gt                 1675 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'CrysAlisPro, Rigaku OD' 
_computing_cell_refinement        'CrysAlisPro, Rigaku OD' 
_computing_data_reduction         'CrysAlisPro, Rigaku OD' 
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2017)' 
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'CIFTAB-2014 (Sheldrick, 2017)' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0385P)²+0.4454P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          2044 
_refine_ls_number_parameters      146 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0525 
_refine_ls_R_factor_gt            0.0403 
_refine_ls_wR_factor_ref          0.1004 
_refine_ls_wR_factor_gt           0.0927 
_refine_ls_goodness_of_fit_ref    1.047 
_refine_ls_restrained_S_all       1.047 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
N1 N 0.22675(7) 0.2845(4) 0.12016(10) 0.0262(3) Uani 1 1 d . . . . . 
N2 N 0.29200(7) 0.2770(4) 0.17834(10) 0.0258(3) Uani 1 1 d . . . . . 
C3 C 0.18052(8) 0.1509(4) 0.17275(12) 0.0235(4) Uani 1 1 d . . . . . 
C4 C 0.11830(9) -0.0170(5) 0.11227(12) 0.0277(4) Uani 1 1 d . . . . . 
F4 F 0.10718(5) -0.0632(3) 0.00654(7) 0.0413(3) Uani 1 1 d . . . . . 
C5 C 0.06861(9) -0.1437(5) 0.15384(14) 0.0302(4) Uani 1 1 d . . . . . 
H5A H 0.027111 -0.258409 0.109484 0.036 Uiso 1 1 calc R U . . . 
C6 C 0.08051(9) -0.1000(5) 0.26220(14) 0.0303(4) Uani 1 1 d . . . . . 
H6A H 0.047342 -0.190106 0.292912 0.036 Uiso 1 1 calc R U . . . 
C7 C 0.14024(9) 0.0735(4) 0.32591(13) 0.0285(4) Uani 1 1 d . . . . . 
H7A H 0.147939 0.107299 0.399849 0.034 Uiso 1 1 calc R U . . . 
C8 C 0.18813(8) 0.1957(4) 0.28049(13) 0.0250(4) Uani 1 1 d . . . . . 
F8 F 0.24406(5) 0.3802(3) 0.34254(7) 0.0350(3) Uani 1 1 d . . . . . 
C9 C 0.33844(8) 0.4160(4) 0.13021(12) 0.0246(4) Uani 1 1 d . . . . . 
C10 C 0.32524(8) 0.5808(4) 0.03311(12) 0.0245(4) Uani 1 1 d . . . . . 
H10A H 0.279705 0.632809 -0.017531 0.029 Uiso 1 1 calc R U . . . 
N11 N 0.38886(7) 0.6521(4) 0.02459(10) 0.0248(3) Uani 1 1 d . . . . . 
N12 N 0.44449(7) 0.5464(4) 0.11155(11) 0.0304(4) Uani 1 1 d . . . . . 
C13 C 0.41333(9) 0.4046(5) 0.17520(13) 0.0298(4) Uani 1 1 d . . . . . 
H13A H 0.438528 0.307234 0.242919 0.036 Uiso 1 1 calc R U . . . 
C14 C 0.40371(9) 0.8121(5) -0.06488(14) 0.0337(4) Uani 1 1 d . . . . . 
H14A H 0.359924 0.816216 -0.127413 0.051 Uiso 1 1 calc R U . . . 
H14B H 0.440714 0.682143 -0.081893 0.051 Uiso 1 1 calc R U . . . 
H14C H 0.420475 1.045567 -0.045508 0.051 Uiso 1 1 calc R U . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
N1 N2 1.2658(18) . ? 
N1 C3 1.425(2) . ? 
N2 C9 1.395(2) . ? 
C3 C4 1.392(2) . ? 
C3 C8 1.397(2) . ? 
C4 F4 1.3569(18) . ? 
C4 C5 1.373(2) . ? 
C5 C6 1.387(2) . ? 
C6 C7 1.383(2) . ? 
C7 C8 1.370(2) . ? 
C8 F8 1.3497(18) . ? 
C9 C10 1.386(2) . ? 
C9 C13 1.404(2) . ? 
C10 N11 1.333(2) . ? 
N11 N12 1.3669(19) . ? 
N11 C14 1.457(2) . ? 
N12 C13 1.324(2) . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
N2 N1 C3 112.75(13) . . ? 
N1 N2 C9 114.10(13) . . ? 
C4 C3 C8 114.90(14) . . ? 
C4 C3 N1 118.92(14) . . ? 
C8 C3 N1 125.95(15) . . ? 
F4 C4 C5 118.42(15) . . ? 
F4 C4 C3 117.73(15) . . ? 
C5 C4 C3 123.84(15) . . ? 
C4 C5 C6 118.35(16) . . ? 
C7 C6 C5 120.56(16) . . ? 
C8 C7 C6 118.81(15) . . ? 
F8 C8 C7 117.96(14) . . ? 
F8 C8 C3 118.51(14) . . ? 
C7 C8 C3 123.48(15) . . ? 
C10 C9 N2 131.25(14) . . ? 
C10 C9 C13 104.75(14) . . ? 
N2 C9 C13 123.99(14) . . ? 
N11 C10 C9 106.65(14) . . ? 
C10 N11 N12 112.60(14) . . ? 
C10 N11 C14 127.88(14) . . ? 
N12 N11 C14 119.49(13) . . ? 
C13 N12 N11 104.40(13) . . ? 
N12 C13 C9 111.60(14) . . ? 
  
_refine_diff_density_max    0.210 
_refine_diff_density_min   -0.197 
_refine_diff_density_rms    0.043 
  
  
  
#===END

 
data_4pzMe-F2
  
_audit_creation_method            'SHELXL-2018/3' 
_shelx_SHELXL_version_number      '2018/3' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 'C12 H12 F2 N4' 
_chemical_formula_sum 
 'C12 H12 F2 N4' 
_chemical_formula_weight          250.26 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'F'  'F'   0.0171   0.0103 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/c' 
_space_group_name_Hall            '-P 2ybc' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
  
_cell_length_a                    9.8817(7) 
_cell_length_b                    16.6285(11) 
_cell_length_c                    7.5309(5) 
_cell_angle_alpha                 90 
_cell_angle_beta                  103.152(7) 
_cell_angle_gamma                 90 
_cell_volume                      1205.00(15) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     1158 
_cell_measurement_theta_min       3.1010 
_cell_measurement_theta_max       27.4740 
  
_exptl_crystal_description        'blocky needles' 
_exptl_crystal_colour             Orange 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.379 
_exptl_crystal_F_000              520 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.668 
_exptl_crystal_size_mid           0.298 
_exptl_crystal_size_min           0.167 
_exptl_absorpt_coefficient_mu     0.109 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.964 
_exptl_absorpt_correction_T_max   0.983 
_exptl_absorpt_process_details     
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
; 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    'Enhance (Mo) X-ray Source' 
_diffrn_measurement_device_type   'Agilent Xcalibur 3 E' 
_diffrn_measurement_method        'omega scans' 
_diffrn_detector_area_resol_mean  16.0382 
_diffrn_reflns_number             4183 
_diffrn_reflns_av_unetI/netI      0.0407 
_diffrn_reflns_av_R_equivalents   0.0200 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -10 
_diffrn_reflns_limit_k_max        21 
_diffrn_reflns_limit_l_min        -9 
_diffrn_reflns_limit_l_max        9 
_diffrn_reflns_theta_min          2.445 
_diffrn_reflns_theta_max          28.061 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.826 
_diffrn_measured_fraction_theta_full  0.990 
_diffrn_reflns_Laue_measured_fraction_max    0.826 
_diffrn_reflns_Laue_measured_fraction_full   0.990 
_diffrn_reflns_point_group_measured_fraction_max   0.826 
_diffrn_reflns_point_group_measured_fraction_full  0.990 
_reflns_number_total              2408 
_reflns_number_gt                 1835 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'CrysAlisPro, Rigaku OD' 
_computing_cell_refinement        'CrysAlisPro, Rigaku OD' 
_computing_data_reduction         'CrysAlisPro, Rigaku OD' 
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2017)' 
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'CIFTAB-2014 (Sheldrick, 2017)' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0403P)²+0.4382P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      'SHELXL-2018/3 (Sheldrick 2018)' 
_refine_ls_extinction_coef        0.010(2) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          2408 
_refine_ls_number_parameters      167 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0626 
_refine_ls_R_factor_gt            0.0439 
_refine_ls_wR_factor_ref          0.1118 
_refine_ls_wR_factor_gt           0.0995 
_refine_ls_goodness_of_fit_ref    1.052 
_refine_ls_restrained_S_all       1.052 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
N1 N 0.27191(14) 0.19867(9) 0.51824(19) 0.0270(4) Uani 1 1 d . . . . . 
N2 N 0.25252(14) 0.12481(9) 0.48267(19) 0.0264(4) Uani 1 1 d . . . . . 
C3 C 0.40108(16) 0.21876(11) 0.6357(2) 0.0246(4) Uani 1 1 d . . . . . 
C4 C 0.42810(17) 0.30073(12) 0.6572(2) 0.0286(4) Uani 1 1 d . . . . . 
F4 F 0.33159(12) 0.35226(7) 0.56552(15) 0.0428(3) Uani 1 1 d . . . . . 
C5 C 0.54769(19) 0.33288(13) 0.7644(3) 0.0356(5) Uani 1 1 d . . . . . 
H5A H 0.561506 0.389398 0.773898 0.043 Uiso 1 1 calc R U . . . 
C6 C 0.64692(19) 0.28000(13) 0.8577(3) 0.0360(5) Uani 1 1 d . . . . . 
H6A H 0.730761 0.300421 0.931737 0.043 Uiso 1 1 calc R U . . . 
C7 C 0.62563(18) 0.19788(13) 0.8445(2) 0.0339(5) Uani 1 1 d . . . . . 
H7A H 0.693671 0.162032 0.910533 0.041 Uiso 1 1 calc R U . . . 
C8 C 0.50487(18) 0.16844(12) 0.7347(2) 0.0302(4) Uani 1 1 d . . . . . 
F8 F 0.48741(12) 0.08836(7) 0.72645(17) 0.0514(4) Uani 1 1 d . . . . . 
C9 C 0.12364(17) 0.10800(10) 0.3666(2) 0.0234(4) Uani 1 1 d . . . . . 
C10 C 0.08151(17) 0.02949(11) 0.3218(2) 0.0260(4) Uani 1 1 d . . . . . 
N11 N -0.04572(15) 0.03496(9) 0.21014(19) 0.0270(3) Uani 1 1 d . . . . . 
N12 N -0.08867(15) 0.11336(9) 0.17772(19) 0.0276(4) Uani 1 1 d . . . . . 
C13 C 0.01408(17) 0.15814(10) 0.2722(2) 0.0228(4) Uani 1 1 d . . . . . 
C14 C 0.1544(2) -0.04780(11) 0.3761(3) 0.0360(5) Uani 1 1 d . . . . . 
H14A H 0.102334 -0.079413 0.447914 0.054 Uiso 1 1 calc R U . . . 
H14B H 0.247997 -0.036999 0.449616 0.054 Uiso 1 1 calc R U . . . 
H14C H 0.161135 -0.078013 0.266716 0.054 Uiso 1 1 calc R U . . . 
C15 C -0.1395(2) -0.02974(12) 0.1333(3) 0.0351(5) Uani 1 1 d . . . . . 
H15A H -0.183393 -0.051526 0.227368 0.053 Uiso 1 1 calc R U . . . 
H15B H -0.087202 -0.072374 0.088957 0.053 Uiso 1 1 calc R U . . . 
H15C H -0.211342 -0.008981 0.031787 0.053 Uiso 1 1 calc R U . . . 
C16 C 0.00325(19) 0.24772(11) 0.2656(2) 0.0289(4) Uani 1 1 d . . . . . 
H16A H 0.080313 0.270013 0.219260 0.043 Uiso 1 1 calc R U . . . 
H16B H 0.007515 0.268514 0.388561 0.043 Uiso 1 1 calc R U . . . 
H16C H -0.085194 0.263426 0.184816 0.043 Uiso 1 1 calc R U . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
N1 N2 1.262(2) . ? 
N1 C3 1.417(2) . ? 
N2 C9 1.399(2) . ? 
C3 C4 1.391(3) . ? 
C3 C8 1.400(2) . ? 
C4 F4 1.349(2) . ? 
C4 C5 1.378(2) . ? 
C5 C6 1.384(3) . ? 
C6 C7 1.382(3) . ? 
C7 C8 1.378(3) . ? 
C8 F8 1.342(2) . ? 
C9 C10 1.388(2) . ? 
C9 C13 1.422(2) . ? 
C10 N11 1.347(2) . ? 
C10 C14 1.485(2) . ? 
N11 N12 1.376(2) . ? 
N11 C15 1.452(2) . ? 
N12 C13 1.328(2) . ? 
C13 C16 1.494(2) . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
N2 N1 C3 115.69(15) . . ? 
N1 N2 C9 113.56(15) . . ? 
C4 C3 C8 115.18(16) . . ? 
C4 C3 N1 115.17(16) . . ? 
C8 C3 N1 129.64(17) . . ? 
F4 C4 C5 117.72(17) . . ? 
F4 C4 C3 117.91(15) . . ? 
C5 C4 C3 124.37(17) . . ? 
C4 C5 C6 117.71(19) . . ? 
C7 C6 C5 120.85(18) . . ? 
C8 C7 C6 119.42(18) . . ? 
F8 C8 C7 117.71(17) . . ? 
F8 C8 C3 119.81(16) . . ? 
C7 C8 C3 122.47(18) . . ? 
C10 C9 N2 121.32(16) . . ? 
C10 C9 C13 106.12(15) . . ? 
N2 C9 C13 132.56(16) . . ? 
N11 C10 C9 105.90(15) . . ? 
N11 C10 C14 123.78(17) . . ? 
C9 C10 C14 130.32(16) . . ? 
C10 N11 N12 112.41(14) . . ? 
C10 N11 C15 128.27(16) . . ? 
N12 N11 C15 119.23(15) . . ? 
C13 N12 N11 105.60(14) . . ? 
N12 C13 C9 109.97(15) . . ? 
N12 C13 C16 120.09(15) . . ? 
C9 C13 C16 129.94(15) . . ? 
  
_refine_diff_density_max    0.247 
_refine_diff_density_min   -0.205 
_refine_diff_density_rms    0.046 
  
  
  
#===END

 
data_4pzMe-OMe2
  
_audit_creation_method            'SHELXL-2018/3' 
_shelx_SHELXL_version_number      '2018/3' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 'C14 H18 N4 O2' 
_chemical_formula_sum 
 'C14 H18 N4 O2' 
_chemical_formula_weight          274.32 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/c' 
_space_group_name_Hall            '-P 2ybc' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
  
_cell_length_a                    7.0910(4) 
_cell_length_b                    20.3120(9) 
_cell_length_c                    10.3246(6) 
_cell_angle_alpha                 90 
_cell_angle_beta                  103.879(6) 
_cell_angle_gamma                 90 
_cell_volume                      1443.67(14) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     1297 
_cell_measurement_theta_min       2.8700 
_cell_measurement_theta_max       27.4140 
  
_exptl_crystal_description        'blocky needles' 
_exptl_crystal_colour             Yellow 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.262 
_exptl_crystal_F_000              584 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.668 
_exptl_crystal_size_mid           0.130 
_exptl_crystal_size_min           0.093 
_exptl_absorpt_coefficient_mu     0.087 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.966 
_exptl_absorpt_correction_T_max   0.992 
_exptl_absorpt_process_details     
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
; 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    'Enhance (Mo) X-ray Source' 
_diffrn_measurement_device_type   'Agilent Xcalibur 3 E' 
_diffrn_measurement_method        'omega scans' 
_diffrn_detector_area_resol_mean  16.0382 
_diffrn_reflns_number             5099 
_diffrn_reflns_av_unetI/netI      0.0448 
_diffrn_reflns_av_R_equivalents   0.0228 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -26 
_diffrn_reflns_limit_k_max        21 
_diffrn_reflns_limit_l_min        -9 
_diffrn_reflns_limit_l_max        13 
_diffrn_reflns_theta_min          2.855 
_diffrn_reflns_theta_max          28.222 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.817 
_diffrn_measured_fraction_theta_full  0.990 
_diffrn_reflns_Laue_measured_fraction_max    0.817 
_diffrn_reflns_Laue_measured_fraction_full   0.990 
_diffrn_reflns_point_group_measured_fraction_max   0.817 
_diffrn_reflns_point_group_measured_fraction_full  0.990 
_reflns_number_total              2913 
_reflns_number_gt                 2211 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'CrysAlisPro, Rigaku OD' 
_computing_cell_refinement        'CrysAlisPro, Rigaku OD' 
_computing_data_reduction         'CrysAlisPro, Rigaku OD' 
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2017)' 
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'CIFTAB-2014 (Sheldrick, 2017)' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0474P)²+0.2130P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          2913 
_refine_ls_number_parameters      186 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0686 
_refine_ls_R_factor_gt            0.0483 
_refine_ls_wR_factor_ref          0.1185 
_refine_ls_wR_factor_gt           0.1075 
_refine_ls_goodness_of_fit_ref    1.068 
_refine_ls_restrained_S_all       1.068 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
N1 N 0.2772(2) 0.58510(6) 0.69643(13) 0.0270(3) Uani 1 1 d . . . . . 
N2 N 0.3465(2) 0.58743(7) 0.82027(14) 0.0371(4) Uani 1 1 d . . . . . 
C3 C 0.3069(2) 0.52531(7) 0.63698(15) 0.0246(4) Uani 1 1 d . . . . . 
C4 C 0.2358(2) 0.51501(8) 0.50070(16) 0.0270(4) Uani 1 1 d . . . . . 
N5 N 0.2789(2) 0.45242(7) 0.47858(13) 0.0292(3) Uani 1 1 d . . . . . 
N6 N 0.3742(2) 0.42051(6) 0.59286(13) 0.0301(3) Uani 1 1 d . . . . . 
C7 C 0.3921(2) 0.46474(8) 0.68950(15) 0.0260(4) Uani 1 1 d . . . . . 
C8 C 0.1341(3) 0.56102(9) 0.39414(17) 0.0349(4) Uani 1 1 d . . . . . 
H8A H 0.073462 0.596506 0.434156 0.052 Uiso 1 1 calc R U . . . 
H8B H 0.033909 0.536996 0.329544 0.052 Uiso 1 1 calc R U . . . 
H8C H 0.228124 0.579800 0.348680 0.052 Uiso 1 1 calc R U . . . 
C9 C 0.2315(3) 0.41522(9) 0.35444(18) 0.0415(5) Uani 1 1 d . . . . . 
H9A H 0.338054 0.384928 0.351832 0.062 Uiso 1 1 calc R U . . . 
H9B H 0.212485 0.445647 0.278742 0.062 Uiso 1 1 calc R U . . . 
H9C H 0.111958 0.390055 0.349194 0.062 Uiso 1 1 calc R U . . . 
C10 C 0.4938(3) 0.44697(8) 0.82921(16) 0.0357(4) Uani 1 1 d . . . . . 
H10A H 0.613788 0.472672 0.856452 0.054 Uiso 1 1 calc R U . . . 
H10B H 0.525388 0.399922 0.833712 0.054 Uiso 1 1 calc R U . . . 
H10C H 0.409097 0.456651 0.889105 0.054 Uiso 1 1 calc R U . . . 
C11 C 0.3060(3) 0.64909(8) 0.87728(16) 0.0345(4) Uani 1 1 d . . . . . 
C12 C 0.1656(3) 0.65009(8) 0.95103(17) 0.0364(4) Uani 1 1 d . . . . . 
C13 C 0.1347(3) 0.70704(9) 1.01786(18) 0.0450(5) Uani 1 1 d . . . . . 
H13A H 0.039815 0.707879 1.069048 0.054 Uiso 1 1 calc R U . . . 
C14 C 0.2438(3) 0.76228(9) 1.0087(2) 0.0507(6) Uani 1 1 d . . . . . 
H14A H 0.222166 0.801224 1.053993 0.061 Uiso 1 1 calc R U . . . 
C15 C 0.3833(3) 0.76278(9) 0.9359(2) 0.0462(5) Uani 1 1 d . . . . . 
H15A H 0.455422 0.801632 0.930120 0.055 Uiso 1 1 calc R U . . . 
C16 C 0.4168(3) 0.70533(8) 0.87097(17) 0.0381(5) Uani 1 1 d . . . . . 
O17 O 0.0675(2) 0.59192(6) 0.95205(12) 0.0428(4) Uani 1 1 d . . . . . 
C18 C -0.0860(3) 0.59078(10) 1.0194(2) 0.0522(5) Uani 1 1 d . . . . . 
H18A H -0.137672 0.545962 1.017846 0.078 Uiso 1 1 calc R U . . . 
H18C H -0.189604 0.620708 0.974614 0.078 Uiso 1 1 calc R U . . . 
H18B H -0.036213 0.604879 1.112114 0.078 Uiso 1 1 calc R U . . . 
O19 O 0.5561(2) 0.69859(6) 0.80049(13) 0.0468(4) Uani 1 1 d . . . . . 
C20 C 0.6657(4) 0.75580(10) 0.7848(2) 0.0601(6) Uani 1 1 d . . . . . 
H20A H 0.758437 0.744714 0.731467 0.090 Uiso 1 1 calc R U . . . 
H20B H 0.736246 0.771675 0.872702 0.090 Uiso 1 1 calc R U . . . 
H20C H 0.577429 0.790272 0.739422 0.090 Uiso 1 1 calc R U . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
N1 N2 1.2558(18) . ? 
N1 C3 1.3994(19) . ? 
N2 C11 1.442(2) . ? 
C3 C4 1.392(2) . ? 
C3 C7 1.419(2) . ? 
C4 N5 1.340(2) . ? 
C4 C8 1.491(2) . ? 
N5 N6 1.3736(18) . ? 
N5 C9 1.456(2) . ? 
N6 C7 1.326(2) . ? 
C7 C10 1.494(2) . ? 
C11 C12 1.391(3) . ? 
C11 C16 1.397(3) . ? 
C12 O17 1.372(2) . ? 
C12 C13 1.391(2) . ? 
C13 C14 1.379(3) . ? 
C14 C15 1.378(3) . ? 
C15 C16 1.395(2) . ? 
C16 O19 1.367(2) . ? 
O17 C18 1.426(2) . ? 
O19 C20 1.428(2) . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
N2 N1 C3 114.58(13) . . ? 
N1 N2 C11 112.38(13) . . ? 
C4 C3 N1 121.17(14) . . ? 
C4 C3 C7 105.89(13) . . ? 
N1 C3 C7 132.81(14) . . ? 
N5 C4 C3 105.83(14) . . ? 
N5 C4 C8 123.96(14) . . ? 
C3 C4 C8 130.21(15) . . ? 
C4 N5 N6 112.75(12) . . ? 
C4 N5 C9 128.94(14) . . ? 
N6 N5 C9 118.26(14) . . ? 
C7 N6 N5 105.37(13) . . ? 
N6 C7 C3 110.16(14) . . ? 
N6 C7 C10 119.97(14) . . ? 
C3 C7 C10 129.86(14) . . ? 
C12 C11 C16 119.89(16) . . ? 
C12 C11 N2 118.36(16) . . ? 
C16 C11 N2 121.45(17) . . ? 
O17 C12 C13 124.89(18) . . ? 
O17 C12 C11 114.97(15) . . ? 
C13 C12 C11 120.14(18) . . ? 
C14 C13 C12 119.00(19) . . ? 
C15 C14 C13 122.10(18) . . ? 
C14 C15 C16 118.91(19) . . ? 
O19 C16 C15 124.62(18) . . ? 
O19 C16 C11 115.44(15) . . ? 
C15 C16 C11 119.94(19) . . ? 
C12 O17 C18 117.73(14) . . ? 
C16 O19 C20 117.45(15) . . ? 
  
_refine_diff_density_max    0.206 
_refine_diff_density_min   -0.195 
_refine_diff_density_rms    0.046 
  
  
  
#===END


data_4pzMe-OMe2_diethylether
  
_audit_creation_method            'SHELXL-2018/3' 
_shelx_SHELXL_version_number      '2018/3' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 'C14 H18 N4 O2' 
_chemical_formula_sum 
 'C14 H18 N4 O2' 
_chemical_formula_weight          274.32 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/c' 
_space_group_name_Hall            '-P 2ybc' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
  
_cell_length_a                    7.0836(4) 
_cell_length_b                    20.2850(12) 
_cell_length_c                    10.3061(6) 
_cell_angle_alpha                 90 
_cell_angle_beta                  103.825(5) 
_cell_angle_gamma                 90 
_cell_volume                      1437.99(14) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     1290 
_cell_measurement_theta_min       3.2760 
_cell_measurement_theta_max       27.4390 
  
_exptl_crystal_description        'blocky needles' 
_exptl_crystal_colour             Yellow 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.267 
_exptl_crystal_F_000              584 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.592 
_exptl_crystal_size_mid           0.224 
_exptl_crystal_size_min           0.121 
_exptl_absorpt_coefficient_mu     0.088 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.980 
_exptl_absorpt_correction_T_max   0.991 
_exptl_absorpt_process_details     
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
; 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    'Enhance (Mo) X-ray Source' 
_diffrn_measurement_device_type   'Agilent Xcalibur 3 E' 
_diffrn_measurement_method        'omega scans' 
_diffrn_detector_area_resol_mean  16.0382 
_diffrn_reflns_number             5252 
_diffrn_reflns_av_unetI/netI      0.0444 
_diffrn_reflns_av_R_equivalents   0.0220 
_diffrn_reflns_limit_h_min        -7 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -24 
_diffrn_reflns_limit_k_max        26 
_diffrn_reflns_limit_l_min        -10 
_diffrn_reflns_limit_l_max        12 
_diffrn_reflns_theta_min          2.859 
_diffrn_reflns_theta_max          28.204 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.812 
_diffrn_measured_fraction_theta_full  0.987 
_diffrn_reflns_Laue_measured_fraction_max    0.812 
_diffrn_reflns_Laue_measured_fraction_full   0.987 
_diffrn_reflns_point_group_measured_fraction_max   0.812 
_diffrn_reflns_point_group_measured_fraction_full  0.987 
_reflns_number_total              2881 
_reflns_number_gt                 2201 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'CrysAlisPro, Rigaku OD' 
_computing_cell_refinement        'CrysAlisPro, Rigaku OD' 
_computing_data_reduction         'CrysAlisPro, Rigaku OD' 
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2017)' 
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'CIFTAB-2014 (Sheldrick, 2017)' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0481P)²+0.3211P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      'SHELXL-2018/3 (Sheldrick 2018)' 
_refine_ls_extinction_coef        0.0067(15) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          2881 
_refine_ls_number_parameters      187 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0696 
_refine_ls_R_factor_gt            0.0484 
_refine_ls_wR_factor_ref          0.1223 
_refine_ls_wR_factor_gt           0.1093 
_refine_ls_goodness_of_fit_ref    1.044 
_refine_ls_restrained_S_all       1.044 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
N1 N 0.27712(19) 0.58513(7) 0.69672(14) 0.0259(3) Uani 1 1 d . . . . . 
N2 N 0.3471(2) 0.58750(7) 0.82040(15) 0.0369(4) Uani 1 1 d . . . . . 
C3 C 0.3068(2) 0.52536(8) 0.63697(17) 0.0237(4) Uani 1 1 d . . . . . 
C4 C 0.2360(2) 0.51499(8) 0.50084(17) 0.0257(4) Uani 1 1 d . . . . . 
N5 N 0.27875(19) 0.45244(7) 0.47853(14) 0.0280(4) Uani 1 1 d . . . . . 
N6 N 0.37408(19) 0.42056(7) 0.59310(15) 0.0293(4) Uani 1 1 d . . . . . 
C7 C 0.3922(2) 0.46490(8) 0.68979(17) 0.0251(4) Uani 1 1 d . . . . . 
C8 C 0.1348(3) 0.56096(9) 0.39403(18) 0.0342(5) Uani 1 1 d . . . . . 
H8A H 0.072605 0.596244 0.433779 0.051 Uiso 1 1 calc R U . . . 
H8B H 0.035735 0.536765 0.328721 0.051 Uiso 1 1 calc R U . . . 
H8C H 0.229416 0.580105 0.349306 0.051 Uiso 1 1 calc R U . . . 
C9 C 0.2325(3) 0.41519(10) 0.35443(19) 0.0400(5) Uani 1 1 d . . . . . 
H9A H 0.338994 0.384661 0.352503 0.060 Uiso 1 1 calc R U . . . 
H9B H 0.214894 0.445601 0.278598 0.060 Uiso 1 1 calc R U . . . 
H9C H 0.112319 0.390192 0.348536 0.060 Uiso 1 1 calc R U . . . 
C10 C 0.4938(3) 0.44705(9) 0.82934(18) 0.0364(5) Uani 1 1 d . . . . . 
H10A H 0.614652 0.472362 0.856255 0.055 Uiso 1 1 calc R U . . . 
H10B H 0.523811 0.399828 0.833956 0.055 Uiso 1 1 calc R U . . . 
H10C H 0.409547 0.457233 0.889552 0.055 Uiso 1 1 calc R U . . . 
C11 C 0.3063(3) 0.64920(9) 0.87718(18) 0.0333(5) Uani 1 1 d . . . . . 
C12 C 0.1661(3) 0.65018(9) 0.95129(18) 0.0349(5) Uani 1 1 d . . . . . 
C13 C 0.1344(3) 0.70714(10) 1.0179(2) 0.0441(5) Uani 1 1 d . . . . . 
H13A H 0.038905 0.707998 1.068831 0.053 Uiso 1 1 calc R U . . . 
C14 C 0.2440(3) 0.76247(10) 1.0088(2) 0.0494(6) Uani 1 1 d . . . . . 
H14A H 0.222260 0.801549 1.053885 0.059 Uiso 1 1 calc R U . . . 
C15 C 0.3836(3) 0.76268(10) 0.9364(2) 0.0451(6) Uani 1 1 d . . . . . 
H15A H 0.456677 0.801454 0.931220 0.054 Uiso 1 1 calc R U . . . 
C16 C 0.4169(3) 0.70548(9) 0.87062(19) 0.0373(5) Uani 1 1 d . . . . . 
O17 O 0.06758(19) 0.59190(6) 0.95232(14) 0.0421(4) Uani 1 1 d . . . . . 
C18 C -0.0857(3) 0.59076(11) 1.0194(2) 0.0506(6) Uani 1 1 d . . . . . 
H18A H -0.136755 0.545810 1.018448 0.076 Uiso 1 1 calc R U . . . 
H18C H -0.189824 0.620451 0.974030 0.076 Uiso 1 1 calc R U . . . 
H18B H -0.036400 0.605230 1.112053 0.076 Uiso 1 1 calc R U . . . 
O19 O 0.5564(2) 0.69857(6) 0.80078(15) 0.0464(4) Uani 1 1 d . . . . . 
C20 C 0.6657(3) 0.75587(11) 0.7848(3) 0.0588(7) Uani 1 1 d . . . . . 
H20A H 0.759873 0.744613 0.732399 0.088 Uiso 1 1 calc R U . . . 
H20B H 0.734795 0.772236 0.872766 0.088 Uiso 1 1 calc R U . . . 
H20C H 0.577429 0.790097 0.738086 0.088 Uiso 1 1 calc R U . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
N1 N2 1.2534(19) . ? 
N1 C3 1.398(2) . ? 
N2 C11 1.440(2) . ? 
C3 C4 1.389(2) . ? 
C3 C7 1.417(2) . ? 
C4 N5 1.337(2) . ? 
C4 C8 1.489(2) . ? 
N5 N6 1.3738(19) . ? 
N5 C9 1.454(2) . ? 
N6 C7 1.326(2) . ? 
C7 C10 1.491(2) . ? 
C11 C12 1.390(3) . ? 
C11 C16 1.395(3) . ? 
C12 O17 1.374(2) . ? 
C12 C13 1.389(3) . ? 
C13 C14 1.381(3) . ? 
C14 C15 1.374(3) . ? 
C15 C16 1.392(3) . ? 
C16 O19 1.361(2) . ? 
O17 C18 1.420(2) . ? 
O19 C20 1.428(2) . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
N2 N1 C3 114.61(14) . . ? 
N1 N2 C11 112.18(14) . . ? 
C4 C3 N1 121.34(15) . . ? 
C4 C3 C7 105.97(15) . . ? 
N1 C3 C7 132.57(15) . . ? 
N5 C4 C3 105.98(14) . . ? 
N5 C4 C8 123.77(16) . . ? 
C3 C4 C8 130.24(16) . . ? 
C4 N5 N6 112.58(14) . . ? 
C4 N5 C9 129.17(16) . . ? 
N6 N5 C9 118.21(15) . . ? 
C7 N6 N5 105.44(13) . . ? 
N6 C7 C3 110.03(15) . . ? 
N6 C7 C10 119.88(15) . . ? 
C3 C7 C10 130.08(15) . . ? 
C12 C11 C16 119.88(17) . . ? 
C12 C11 N2 118.36(17) . . ? 
C16 C11 N2 121.44(18) . . ? 
O17 C12 C13 124.69(19) . . ? 
O17 C12 C11 115.02(16) . . ? 
C13 C12 C11 120.30(18) . . ? 
C14 C13 C12 118.8(2) . . ? 
C15 C14 C13 121.94(19) . . ? 
C14 C15 C16 119.3(2) . . ? 
O19 C16 C15 124.89(19) . . ? 
O19 C16 C11 115.35(16) . . ? 
C15 C16 C11 119.7(2) . . ? 
C12 O17 C18 117.82(15) . . ? 
C16 O19 C20 117.35(16) . . ? 
  
_refine_diff_density_max    0.227 
_refine_diff_density_min   -0.162 
_refine_diff_density_rms    0.039 
  
  
  
#===END



