 
data_cu_DP_24_0m_a
 
_audit_creation_method            'SHELXL-2019/1'
_shelx_SHELXL_version_number      '2019/1'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C14 H15 N3 O, C5 H6 O'
_chemical_formula_sum             'C19 H21 N3 O2' 
_chemical_formula_weight          323.39

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0311   0.0180
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0492   0.0322
 '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'
 
_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                    5.33600(10)
_cell_length_b                    16.4504(4)
_cell_length_c                    21.5018(6)
_cell_angle_alpha                 90
_cell_angle_beta                  94.726(2)
_cell_angle_gamma                 90
_cell_volume                      1881.00(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     220(2)
_cell_measurement_reflns_used     4189
_cell_measurement_theta_min       3.39
_cell_measurement_theta_max       58.27
 
_exptl_crystal_description        'elongated needle'
_exptl_crystal_colour             yellow
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.142          
_exptl_crystal_F_000              688
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.025
_exptl_crystal_size_mid           0.020
_exptl_crystal_size_min           0.010
_exptl_absorpt_coefficient_mu     0.606
_shelx_estimated_absorpt_T_min    0.988
_shelx_estimated_absorpt_T_max    0.994
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6540
_exptl_absorpt_correction_T_max   0.7516
_exptl_absorpt_process_details    
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1384 before and 0.0560 after correction.
The Ratio of minimum to maximum transmission is 0.8701.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       220(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             14243
_diffrn_reflns_av_unetI/netI      0.0281
_diffrn_reflns_av_R_equivalents   0.0408
_diffrn_reflns_limit_h_min        -5
_diffrn_reflns_limit_h_max        5
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          3.387
_diffrn_reflns_theta_max          59.081
_diffrn_reflns_theta_full         59.081
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              2688
_reflns_number_gt                 2019
_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        'Bruker APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement   'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_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)+(0.1848P)²+2.2846P] 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          2688
_refine_ls_number_parameters      218
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1198
_refine_ls_R_factor_gt            0.0968
_refine_ls_wR_factor_ref          0.3164
_refine_ls_wR_factor_gt           0.2876
_refine_ls_goodness_of_fit_ref    1.085
_refine_ls_restrained_S_all       1.085
_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
O001 O 0.7684(6) 0.3838(2) 0.35750(15) 0.0629(10) Uani 1 1 d . . . . .
O002 O 0.9986(10) 0.1665(3) 0.2162(2) 0.1036(15) Uani 1 1 d . . . . .
N001 N 0.2205(7) 0.4111(2) 0.51273(16) 0.0497(10) Uani 1 1 d . . . . .
H001 H 0.097385 0.429180 0.533005 0.060 Uiso 1 1 calc R U . . .
N002 N 0.1816(6) 0.5070(2) 0.42870(16) 0.0490(10) Uani 1 1 d . . . . .
N003 N 0.4748(7) 0.4867(2) 0.35303(16) 0.0507(10) Uani 1 1 d . . . . .
C00A C 0.2809(8) 0.5261(3) 0.3771(2) 0.0515(11) Uani 1 1 d . . . . .
H00A H 0.212139 0.570986 0.354589 0.062 Uiso 1 1 calc R U . . .
C00B C 0.3765(8) 0.3460(3) 0.5306(2) 0.0514(11) Uani 1 1 d . . . . .
C00C C 0.9946(12) 0.2488(3) 0.2995(3) 0.0754(17) Uani 1 1 d . . . . .
H00C H 0.906958 0.290196 0.318664 0.090 Uiso 1 1 calc R U . . .
C00D C 0.7339(9) 0.2752(3) 0.4936(3) 0.0643(14) Uani 1 1 d . . . . .
H00D H 0.854016 0.268004 0.464449 0.077 Uiso 1 1 calc R U . . .
C00E C 0.5638(10) 0.5156(3) 0.2935(2) 0.0622(13) Uani 1 1 d . . . . .
H00B H 0.748054 0.515832 0.296772 0.075 Uiso 1 1 calc R U . . .
H00E H 0.506093 0.571556 0.285727 0.075 Uiso 1 1 calc R U . . .
C00F C 0.3782(9) 0.2969(3) 0.5828(2) 0.0620(13) Uani 1 1 d . . . . .
H00F H 0.260788 0.303683 0.612703 0.074 Uiso 1 1 calc R U . . .
C00G C 0.5596(10) 0.2378(4) 0.5889(3) 0.0749(16) Uani 1 1 d . . . . .
H00G H 0.565152 0.203477 0.623984 0.090 Uiso 1 1 calc R U . . .
C00H C 0.7351(10) 0.2263(4) 0.5457(3) 0.0759(16) Uani 1 1 d . . . . .
H00H H 0.855921 0.184908 0.551947 0.091 Uiso 1 1 calc R U . . .
C00I C 0.9007(14) 0.2174(4) 0.2485(4) 0.097(2) Uani 1 1 d . . . . .
H00I H 0.738848 0.235096 0.233997 0.116 Uiso 1 1 calc R U . . .
C00J C 0.4665(11) 0.4616(4) 0.2385(3) 0.0835(18) Uani 1 1 d . . . . .
H00J H 0.539395 0.481125 0.200905 0.100 Uiso 1 1 calc R U . . .
H00K H 0.528909 0.406232 0.246578 0.100 Uiso 1 1 calc R U . . .
C00K C 0.1124(12) 0.4059(5) 0.1685(3) 0.095(2) Uani 1 1 d . . . . .
H00L H -0.069527 0.407041 0.161676 0.142 Uiso 1 1 calc R U . . .
H00M H 0.168356 0.350321 0.175625 0.142 Uiso 1 1 calc R U . . .
H00N H 0.185281 0.427461 0.132079 0.142 Uiso 1 1 calc R U . . .
C00L C 0.1963(13) 0.4578(5) 0.2256(3) 0.092(2) Uani 1 1 d . . . . .
H00O H 0.131304 0.513132 0.218950 0.111 Uiso 1 1 calc R U . . .
H00P H 0.122274 0.435498 0.262196 0.111 Uiso 1 1 calc R U . . .
C00M C 1.261(2) 0.2183(10) 0.3310(6) 0.214(8) Uani 1 1 d . . . . .
H00Q H 1.419045 0.234802 0.319501 0.256 Uiso 1 1 calc R U . . .
C00N C 1.289(3) 0.0836(11) 0.4408(7) 0.241(8) Uani 1 1 d . . . . .
H00R H 1.458093 0.067041 0.446493 0.289 Uiso 1 1 calc R U . . .
H00S H 1.169489 0.060627 0.465385 0.289 Uiso 1 1 calc R U . . .
C00O C 1.207(3) 0.1487(8) 0.3909(11) 0.264(10) Uani 1 1 d . . . . .
H00T H 1.034018 0.153972 0.394781 0.316 Uiso 1 1 calc R U . . .
C005 C 0.2923(8) 0.4417(3) 0.45865(19) 0.0454(11) Uani 1 1 d . . . . .
C006 C 0.4943(7) 0.3974(3) 0.43922(19) 0.0464(11) Uani 1 1 d . . . . .
C008 C 0.5507(8) 0.3355(3) 0.4850(2) 0.0510(11) Uani 1 1 d . . . . .
C009 C 0.5950(8) 0.4179(3) 0.3821(2) 0.0513(12) Uani 1 1 d . . . . .
 
 
_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
O001 C009 1.237(5) . ?
O002 C00I 1.232(7) . ?
N001 C005 1.351(5) . ?
N001 C00B 1.392(6) . ?
N002 C00A 1.307(5) . ?
N002 C005 1.362(6) . ?
N003 C00A 1.358(6) . ?
N003 C009 1.421(6) . ?
N003 C00E 1.480(6) . ?
C00B C00F 1.383(7) . ?
C00B C008 1.415(6) . ?
C00C C00I 1.276(9) . ?
C00C C00M 1.603(17) . ?
C00D C00H 1.378(8) . ?
C00D C008 1.394(7) . ?
C00E C00J 1.536(8) . ?
C00F C00G 1.370(8) . ?
C00G C00H 1.386(8) . ?
C00J C00L 1.447(9) . ?
C00K C00L 1.532(9) . ?
C00M C00O 1.76(2) . ?
C00N C00O 1.55(2) . ?
C005 C006 1.394(6) . ?
C006 C009 1.422(6) . ?
C006 C008 1.431(6) . ?
 
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
C005 N001 C00B 108.6(4) . . ?
C00A N002 C005 113.6(4) . . ?
C00A N003 C009 122.9(4) . . ?
C00A N003 C00E 119.0(4) . . ?
C009 N003 C00E 118.1(4) . . ?
N002 C00A N003 125.7(4) . . ?
C00F C00B N001 129.6(4) . . ?
C00F C00B C008 122.0(4) . . ?
N001 C00B C008 108.4(4) . . ?
C00I C00C C00M 120.5(6) . . ?
C00H C00D C008 118.6(5) . . ?
N003 C00E C00J 111.6(4) . . ?
C00G C00F C00B 116.7(5) . . ?
C00F C00G C00H 122.9(5) . . ?
C00D C00H C00G 120.5(5) . . ?
O002 C00I C00C 127.3(7) . . ?
C00L C00J C00E 116.1(5) . . ?
C00J C00L C00K 113.4(5) . . ?
C00C C00M C00O 108.8(7) . . ?
C00N C00O C00M 154.1(16) . . ?
N001 C005 N002 123.9(4) . . ?
N001 C005 C006 110.1(4) . . ?
N002 C005 C006 126.0(4) . . ?
C005 C006 C009 119.4(4) . . ?
C005 C006 C008 106.9(4) . . ?
C009 C006 C008 133.7(4) . . ?
C00D C008 C00B 119.3(4) . . ?
C00D C008 C006 134.6(4) . . ?
C00B C008 C006 106.1(4) . . ?
O001 C009 N003 120.0(4) . . ?
O001 C009 C006 127.7(5) . . ?
N003 C009 C006 112.3(4) . . ?
 
_refine_diff_density_max    0.711
_refine_diff_density_min   -0.331
_refine_diff_density_rms    0.079


# start Validation Reply Form
_vrf_THETM01_cu_DP_24_0m_a
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: These were weakly diffracting crystals, especially in higher
angles. Although a high-brilliance IuS microfocus with Cu radiation was used
reasonable diffraction data could be obtained only to moderate resolution,
despite multiple attempts to improve crystal quality.
;
# end Validation Reply Form

