 
data_pg1_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          ?
_chemical_formula_sum
 'C17 H11 N3 O2' 
_chemical_formula_weight          289.29

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                    10.8188(12)
_cell_length_b                    12.0531(14)
_cell_length_c                    10.7851(11)
_cell_angle_alpha                 90
_cell_angle_beta                  105.194(4)
_cell_angle_gamma                 90
_cell_volume                      1357.2(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        ?
_exptl_crystal_colour             ?
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.416          
_exptl_crystal_F_000              600
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           ?
_exptl_crystal_size_mid           ?
_exptl_crystal_size_min           ?
_exptl_absorpt_coefficient_mu     0.096
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   ?
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             12251
_diffrn_reflns_av_unetI/netI      0.0528
_diffrn_reflns_av_R_equivalents   0.0634
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          2.581
_diffrn_reflns_theta_max          25.998
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.929
_diffrn_measured_fraction_theta_full  0.935
_diffrn_reflns_Laue_measured_fraction_max    0.929
_diffrn_reflns_Laue_measured_fraction_full   0.935
_diffrn_reflns_point_group_measured_fraction_max   0.929
_diffrn_reflns_point_group_measured_fraction_full  0.935
_reflns_number_total              2475
_reflns_number_gt                 1895
_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        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_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)+(0.0635P)²+1.2739P] 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          2475
_refine_ls_number_parameters      199
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0992
_refine_ls_R_factor_gt            0.0743
_refine_ls_wR_factor_ref          0.1690
_refine_ls_wR_factor_gt           0.1570
_refine_ls_goodness_of_fit_ref    1.132
_refine_ls_restrained_S_all       1.132
_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
O1 O 0.7790(2) 0.68294(18) 0.1195(2) 0.0359(6) Uani 1 1 d . . . . .
O2 O 0.7967(3) 0.5688(2) -0.0305(2) 0.0498(7) Uani 1 1 d . . . . .
N2 N 0.7260(3) 0.5579(2) 0.3408(2) 0.0288(6) Uani 1 1 d . . . . .
N3 N 0.5595(3) 0.5710(2) 0.1550(2) 0.0280(6) Uani 1 1 d . . . . .
N4 N 0.8051(3) 0.5913(2) 0.0829(2) 0.0334(7) Uani 1 1 d . . . . .
C1 C 0.7330(3) 0.5164(2) 0.4654(3) 0.0287(7) Uani 1 1 d . . . . .
C2 C 0.8276(3) 0.4354(2) 0.4976(3) 0.0307(7) Uani 1 1 d . . . . .
C3 C 0.8519(3) 0.3814(3) 0.6156(3) 0.0353(8) Uani 1 1 d . . . . .
H3 H 0.916480 0.326131 0.638142 0.042 Uiso 1 1 calc R U . . .
C4 C 0.7799(4) 0.4102(3) 0.6990(3) 0.0390(8) Uani 1 1 d . . . . .
H4 H 0.795300 0.374691 0.780215 0.047 Uiso 1 1 calc R U . . .
C5 C 0.6847(3) 0.4908(3) 0.6652(3) 0.0386(8) Uani 1 1 d . . . . .
H5 H 0.636142 0.508721 0.724133 0.046 Uiso 1 1 calc R U . . .
C6 C 0.6588(3) 0.5456(3) 0.5487(3) 0.0334(8) Uani 1 1 d . . . . .
H6 H 0.593714 0.600444 0.526354 0.040 Uiso 1 1 calc R U . . .
C7 C 0.8165(3) 0.5000(2) 0.2953(3) 0.0283(7) Uani 1 1 d . . . . .
C8 C 0.8815(3) 0.4243(2) 0.3881(3) 0.0287(7) Uani 1 1 d . . . . .
C9 C 0.8527(3) 0.5066(3) 0.1788(3) 0.0302(7) Uani 1 1 d . . . . .
C10 C 0.9470(3) 0.4364(3) 0.1585(3) 0.0349(8) Uani 1 1 d . . . . .
H10 H 0.967534 0.438048 0.078121 0.042 Uiso 1 1 calc R U . . .
C11 C 1.0117(3) 0.3643(3) 0.2527(3) 0.0353(8) Uani 1 1 d . . . . .
H11 H 1.078401 0.319217 0.237817 0.042 Uiso 1 1 calc R U . . .
C12 C 0.9801(3) 0.3574(3) 0.3680(3) 0.0346(8) Uani 1 1 d . . . . .
H12 H 1.024585 0.307847 0.432972 0.042 Uiso 1 1 calc R U . . .
C13 C 0.6195(3) 0.6185(2) 0.2656(3) 0.0266(7) Uani 1 1 d . . . . .
C14 C 0.4609(3) 0.6275(3) 0.0808(3) 0.0316(7) Uani 1 1 d . . . . .
H14 H 0.417879 0.596759 -0.000056 0.038 Uiso 1 1 calc R U . . .
C15 C 0.4184(3) 0.7279(3) 0.1152(3) 0.0348(8) Uani 1 1 d . . . . .
H15 H 0.347147 0.764491 0.060057 0.042 Uiso 1 1 calc R U . . .
C16 C 0.4819(3) 0.7738(3) 0.2315(3) 0.0364(8) Uani 1 1 d . . . . .
H16 H 0.454351 0.842582 0.258089 0.044 Uiso 1 1 calc R U . . .
C17 C 0.5852(3) 0.7193(3) 0.3087(3) 0.0317(8) Uani 1 1 d . . . . .
H17 H 0.631524 0.749599 0.388723 0.038 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
O1 N4 1.231(3) . ?
O2 N4 1.232(3) . ?
N2 C7 1.393(4) . ?
N2 C1 1.417(4) . ?
N2 C13 1.424(4) . ?
N3 C13 1.329(4) . ?
N3 C14 1.340(4) . ?
N4 C9 1.449(4) . ?
C1 C2 1.391(5) . ?
C1 C6 1.398(4) . ?
C2 C3 1.391(4) . ?
C2 C8 1.453(4) . ?
C3 C4 1.380(5) . ?
C4 C5 1.392(5) . ?
C5 C6 1.381(4) . ?
C7 C8 1.400(4) . ?
C7 C9 1.412(4) . ?
C8 C12 1.399(4) . ?
C9 C10 1.387(5) . ?
C10 C11 1.380(5) . ?
C11 C12 1.376(4) . ?
C13 C17 1.385(4) . ?
C14 C15 1.379(4) . ?
C15 C16 1.378(5) . ?
C16 C17 1.374(5) . ?
 
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
C7 N2 C1 106.8(2) . . ?
C7 N2 C13 126.5(2) . . ?
C1 N2 C13 123.8(2) . . ?
C13 N3 C14 116.2(3) . . ?
O1 N4 O2 123.5(3) . . ?
O1 N4 C9 118.1(2) . . ?
O2 N4 C9 118.3(3) . . ?
C2 C1 C6 121.6(3) . . ?
C2 C1 N2 109.8(2) . . ?
C6 C1 N2 128.6(3) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 C8 132.9(3) . . ?
C1 C2 C8 106.7(3) . . ?
C4 C3 C2 118.4(3) . . ?
C3 C4 C5 120.6(3) . . ?
C6 C5 C4 122.1(3) . . ?
C5 C6 C1 116.8(3) . . ?
N2 C7 C8 110.0(2) . . ?
N2 C7 C9 132.0(3) . . ?
C8 C7 C9 118.0(3) . . ?
C12 C8 C7 121.7(3) . . ?
C12 C8 C2 131.6(3) . . ?
C7 C8 C2 106.7(3) . . ?
C10 C9 C7 119.5(3) . . ?
C10 C9 N4 117.1(2) . . ?
C7 C9 N4 123.1(3) . . ?
C11 C10 C9 121.4(3) . . ?
C12 C11 C10 120.3(3) . . ?
C11 C12 C8 119.0(3) . . ?
N3 C13 C17 124.6(3) . . ?
N3 C13 N2 114.9(3) . . ?
C17 C13 N2 120.5(3) . . ?
N3 C14 C15 123.7(3) . . ?
C16 C15 C14 118.4(3) . . ?
C17 C16 C15 119.4(3) . . ?
C16 C17 C13 117.6(3) . . ?
 
_refine_diff_density_max    0.246
_refine_diff_density_min   -0.225
_refine_diff_density_rms    0.060



