# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_522
_database_code_depnum_ccdc_archive 'CCDC 2011731'
loop_
_audit_author_name
_audit_author_address
'Boris Shivachev'
;Institute of Mineralogy and Crystallography
Bulgaria
;
_audit_update_record             
;
2020-06-23 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;
_audit_creation_date             2019-07-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 N4 O4'
_chemical_formula_sum            'C22 H16 N4 O4'
_chemical_formula_weight         400.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H30 N4 O4'
_chemical_oxdiff_usercomment     'SB3-ph Petya'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.5170(5)
_cell_length_b                   10.8616(7)
_cell_length_c                   18.5972(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.902(5)
_cell_angle_gamma                90
_cell_volume                     1887.70(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4547
_cell_measurement_temperature    290
_cell_measurement_theta_max      27.3740
_cell_measurement_theta_min      3.6910
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11248
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.400
_diffrn_reflns_theta_min         2.809
_diffrn_ambient_temperature      290
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3974
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  44.00   1.00   19.00    --    7.52  77.00 -30.00   63
  2  ω    -22.00  49.00   1.00   19.00    --    7.52  77.00-180.00   71
  3  ω    -16.00  25.00   1.00   19.00    --    7.52 -99.00  90.00   41
  4  ω    -18.00   9.00   1.00   19.00    --   -8.15 -99.00   0.00   27
  5  ω    -16.00  11.00   1.00   19.00    --   -8.15 -99.00  60.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0258391000
_diffrn_orient_matrix_UB_12      0.0519767000
_diffrn_orient_matrix_UB_13      -0.0215026000
_diffrn_orient_matrix_UB_21      0.0588621000
_diffrn_orient_matrix_UB_22      -0.0040930000
_diffrn_orient_matrix_UB_23      -0.0183060000
_diffrn_orient_matrix_UB_31      -0.0404524000
_diffrn_orient_matrix_UB_32      -0.0391670000
_diffrn_orient_matrix_UB_33      -0.0267096000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2847
_reflns_number_total             4009
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4009
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²+0.5121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1250
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C10(H10), C9(H9), C5A(H5A), C16(H16), C9A(H9A), C7(H7),
 C5(H5), C6A(H6A), C15(H15), C8(H8), C7A(H7A), C6(H6), C8A(H8A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O2 O 0.47595(13) 0.41527(11) 0.32542(7) 0.0477(3) Uani 1 1 d . . . . .
N2 N 0.67017(14) 0.31402(14) 0.29580(8) 0.0430(4) Uani 1 1 d . . . . .
N1 N 0.56361(15) 0.16690(16) 0.22414(9) 0.0462(4) Uani 1 1 d . . . . .
O1 O 0.80893(13) 0.17056(14) 0.24616(8) 0.0613(4) Uani 1 1 d . . . . .
N3 N 0.76888(16) 0.39280(15) 0.33680(9) 0.0477(4) Uani 1 1 d . . . . .
C3 C 0.44472(17) 0.23605(16) 0.24370(9) 0.0400(4) Uani 1 1 d . . . . .
N14 N 1.3104(2) 0.6983(2) 0.50122(10) 0.0637(5) Uani 1 1 d . . . . .
C4 C 0.35828(17) 0.15413(16) 0.28684(9) 0.0395(4) Uani 1 1 d . . . . .
C2 C 0.52695(18) 0.33436(16) 0.29364(9) 0.0396(4) Uani 1 1 d . . . . .
C12 C 0.9624(2) 0.56602(19) 0.41157(11) 0.0539(5) Uani 1 1 d . . . . .
H12 H 0.865587 0.585356 0.404788 0.065 Uiso 1 1 calc R . . . .
C4A C 0.35490(17) 0.29734(17) 0.17587(10) 0.0418(4) Uani 1 1 d . . . . .
C14 C 1.2044(2) 0.61402(19) 0.45975(10) 0.0510(5) Uani 1 1 d . . . . .
C13 C 1.0615(2) 0.6452(2) 0.44990(11) 0.0557(5) Uani 1 1 d . . . . .
H13 H 1.032967 0.718283 0.468846 0.067 Uiso 1 1 calc R . . . .
C10 C 0.9015(2) 0.3721(2) 0.34159(11) 0.0560(5) Uani 1 1 d . . . . .
H10 H 0.932356 0.303399 0.319103 0.067 Uiso 1 1 calc R . . . .
C1 C 0.69341(18) 0.21012(17) 0.25332(10) 0.0445(4) Uani 1 1 d . . . . .
C11 C 1.00515(19) 0.45748(19) 0.38286(10) 0.0492(5) Uani 1 1 d . . . . .
O14A O 1.43656(18) 0.66949(19) 0.51064(10) 0.0907(6) Uani 1 1 d . . . . .
C9 C 0.21171(19) 0.14161(18) 0.26819(10) 0.0479(5) Uani 1 1 d . . . . .
H9 H 0.160796 0.188102 0.229965 0.058 Uiso 1 1 calc R . . . .
C5A C 0.26126(19) 0.39279(18) 0.18263(10) 0.0477(4) Uani 1 1 d . . . . .
H5A H 0.250226 0.418719 0.228901 0.057 Uiso 1 1 calc R . . . .
C16 C 1.1502(2) 0.4299(2) 0.39305(11) 0.0572(5) Uani 1 1 d . . . . .
H16 H 1.179679 0.357907 0.373213 0.069 Uiso 1 1 calc R . . . .
C9A C 0.3671(2) 0.2596(2) 0.10626(11) 0.0540(5) Uani 1 1 d . . . . .
H9A H 0.428396 0.195103 0.100619 0.065 Uiso 1 1 calc R . . . .
C7 C 0.2129(2) -0.0079(2) 0.36220(11) 0.0584(5) Uani 1 1 d . . . . .
H7 H 0.164515 -0.063817 0.386530 0.070 Uiso 1 1 calc R . . . .
C5 C 0.4311(2) 0.0869(2) 0.34566(11) 0.0552(5) Uani 1 1 d . . . . .
H5 H 0.529500 0.096156 0.360096 0.066 Uiso 1 1 calc R . . . .
O14B O 1.2669(2) 0.79246(19) 0.52578(11) 0.0954(6) Uani 1 1 d . . . . .
C6A C 0.1844(2) 0.4495(2) 0.12113(11) 0.0578(5) Uani 1 1 d . . . . .
H6A H 0.123003 0.514127 0.126290 0.069 Uiso 1 1 calc R . . . .
C15 C 1.2511(2) 0.5078(2) 0.43218(11) 0.0582(5) Uani 1 1 d . . . . .
H15 H 1.348009 0.488758 0.439645 0.070 Uiso 1 1 calc R . . . .
C8 C 0.1397(2) 0.0608(2) 0.30568(11) 0.0553(5) Uani 1 1 d . . . . .
H8 H 0.040917 0.052966 0.292385 0.066 Uiso 1 1 calc R . . . .
C7A C 0.1979(2) 0.4113(2) 0.05253(12) 0.0634(6) Uani 1 1 d . . . . .
H7A H 0.145356 0.449486 0.011311 0.076 Uiso 1 1 calc R . . . .
C6 C 0.3587(2) 0.0065(2) 0.38284(12) 0.0628(6) Uani 1 1 d . . . . .
H6 H 0.408586 -0.038402 0.422107 0.075 Uiso 1 1 calc R . . . .
C8A C 0.2890(2) 0.3166(2) 0.04490(11) 0.0648(6) Uani 1 1 d . . . . .
H8A H 0.298447 0.290624 -0.001596 0.078 Uiso 1 1 calc R . . . .
H1 H 0.552(2) 0.099(2) 0.2030(11) 0.052(6) Uiso 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
O2 C2 1.211(2) . ?
N2 N3 1.387(2) . ?
N2 C2 1.374(2) . ?
N2 C1 1.419(2) . ?
N1 C3 1.460(2) . ?
N1 C1 1.337(2) . ?
N1 H1 0.83(2) . ?
O1 C1 1.211(2) . ?
N3 C10 1.268(2) . ?
C3 C4 1.537(2) . ?
C3 C2 1.530(2) . ?
C3 C4A 1.535(2) . ?
N14 C14 1.469(3) . ?
N14 O14A 1.221(2) . ?
N14 O14B 1.224(3) . ?
C4 C9 1.379(2) . ?
C4 C5 1.387(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(3) . ?
C12 C11 1.387(3) . ?
C4A C5A 1.388(3) . ?
C4A C9A 1.384(3) . ?
C14 C13 1.379(3) . ?
C14 C15 1.370(3) . ?
C13 H13 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.462(3) . ?
C11 C16 1.390(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.381(3) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.381(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.379(3) . ?
C9A H9A 0.9300 . ?
C9A C8A 1.385(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.367(3) . ?
C7 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(3) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.370(3) . ?
C15 H15 0.9300 . ?
C8 H8 0.9300 . ?
C7A H7A 0.9300 . ?
C7A C8A 1.369(3) . ?
C6 H6 0.9300 . ?
C8A H8A 0.9300 . ?

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
N3 N2 C1 129.49(14) . . ?
C2 N2 N3 118.80(15) . . ?
C2 N2 C1 111.71(14) . . ?
C3 N1 H1 122.5(14) . . ?
C1 N1 C3 114.73(16) . . ?
C1 N1 H1 121.9(14) . . ?
C10 N3 N2 119.38(17) . . ?
N1 C3 C4 110.42(14) . . ?
N1 C3 C2 100.29(13) . . ?
N1 C3 C4A 110.83(14) . . ?
C2 C3 C4 110.50(14) . . ?
C2 C3 C4A 109.72(14) . . ?
C4A C3 C4 114.21(13) . . ?
O14A N14 C14 118.3(2) . . ?
O14A N14 O14B 123.6(2) . . ?
O14B N14 C14 118.00(19) . . ?
C9 C4 C3 122.80(16) . . ?
C9 C4 C5 118.49(17) . . ?
C5 C4 C3 118.68(15) . . ?
O2 C2 N2 126.13(16) . . ?
O2 C2 C3 126.64(15) . . ?
N2 C2 C3 107.24(14) . . ?
C13 C12 H12 119.7 . . ?
C13 C12 C11 120.65(18) . . ?
C11 C12 H12 119.7 . . ?
C5A C4A C3 121.11(16) . . ?
C9A C4A C3 120.53(16) . . ?
C9A C4A C5A 118.36(17) . . ?
C13 C14 N14 118.6(2) . . ?
C15 C14 N14 118.84(18) . . ?
C15 C14 C13 122.54(18) . . ?
C12 C13 C14 118.6(2) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
N3 C10 H10 120.4 . . ?
N3 C10 C11 119.25(19) . . ?
C11 C10 H10 120.4 . . ?
N1 C1 N2 106.02(15) . . ?
O1 C1 N2 125.73(17) . . ?
O1 C1 N1 128.25(18) . . ?
C12 C11 C10 121.56(17) . . ?
C12 C11 C16 119.14(18) . . ?
C16 C11 C10 119.29(19) . . ?
C4 C9 H9 119.7 . . ?
C4 C9 C8 120.70(18) . . ?
C8 C9 H9 119.7 . . ?
C4A C5A H5A 119.8 . . ?
C6A C5A C4A 120.44(18) . . ?
C6A C5A H5A 119.8 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.9(2) . . ?
C15 C16 H16 119.6 . . ?
C4A C9A H9A 119.6 . . ?
C4A C9A C8A 120.76(19) . . ?
C8A C9A H9A 119.6 . . ?
C8 C7 H7 120.2 . . ?
C8 C7 C6 119.51(19) . . ?
C6 C7 H7 120.2 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.52(18) . . ?
C6 C5 H5 119.7 . . ?
C5A C6A H6A 119.7 . . ?
C7A C6A C5A 120.5(2) . . ?
C7A C6A H6A 119.7 . . ?
C14 C15 C16 118.14(18) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C9 C8 H8 119.8 . . ?
C7 C8 C9 120.39(18) . . ?
C7 C8 H8 119.8 . . ?
C6A C7A H7A 120.1 . . ?
C8A C7A C6A 119.8(2) . . ?
C8A C7A H7A 120.1 . . ?
C7 C6 H6 119.8 . . ?
C5 C6 C7 120.34(19) . . ?
C5 C6 H6 119.8 . . ?
C9A C8A H8A 119.9 . . ?
C7A C8A C9A 120.1(2) . . ?
C7A C8A H8A 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 O1 0.93 2.17 2.851(3) 129.5 .
N1 H1 O2 0.83(2) 2.07(2) 2.886(2) 167(2) 2_645

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N3 C10 C11 178.04(16) . . . . ?
N1 C3 C4 C9 -128.68(18) . . . . ?
N1 C3 C4 C5 49.2(2) . . . . ?
N1 C3 C2 O2 -179.00(17) . . . . ?
N1 C3 C2 N2 1.05(17) . . . . ?
N1 C3 C4A C5A -162.66(16) . . . . ?
N1 C3 C4A C9A 16.4(2) . . . . ?
N3 N2 C2 O2 -1.0(3) . . . . ?
N3 N2 C2 C3 178.90(14) . . . . ?
N3 N2 C1 N1 -179.35(16) . . . . ?
N3 N2 C1 O1 0.8(3) . . . . ?
N3 C10 C11 C12 -5.6(3) . . . . ?
N3 C10 C11 C16 174.96(19) . . . . ?
C3 N1 C1 N2 0.1(2) . . . . ?
C3 N1 C1 O1 179.92(19) . . . . ?
C3 C4 C9 C8 175.74(17) . . . . ?
C3 C4 C5 C6 -175.87(19) . . . . ?
C3 C4A C5A C6A 178.04(17) . . . . ?
C3 C4A C9A C8A -178.36(18) . . . . ?
N14 C14 C13 C12 -179.57(17) . . . . ?
N14 C14 C15 C16 -179.69(18) . . . . ?
C4 C3 C2 O2 -62.5(2) . . . . ?
C4 C3 C2 N2 117.56(15) . . . . ?
C4 C3 C4A C5A 71.9(2) . . . . ?
C4 C3 C4A C9A -109.03(18) . . . . ?
C4 C9 C8 C7 0.3(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C2 N2 N3 C10 177.21(17) . . . . ?
C2 N2 C1 N1 0.7(2) . . . . ?
C2 N2 C1 O1 -179.16(18) . . . . ?
C2 C3 C4 C9 121.28(18) . . . . ?
C2 C3 C4 C5 -60.8(2) . . . . ?
C2 C3 C4A C5A -52.8(2) . . . . ?
C2 C3 C4A C9A 126.28(17) . . . . ?
C12 C11 C16 C15 1.1(3) . . . . ?
C4A C3 C4 C9 -3.0(2) . . . . ?
C4A C3 C4 C5 174.94(16) . . . . ?
C4A C3 C2 O2 64.3(2) . . . . ?
C4A C3 C2 N2 -115.63(15) . . . . ?
C4A C5A C6A C7A 0.9(3) . . . . ?
C4A C9A C8A C7A -0.3(3) . . . . ?
C13 C12 C11 C10 -179.73(19) . . . . ?
C13 C12 C11 C16 -0.3(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C10 C11 C16 C15 -179.49(19) . . . . ?
C1 N2 N3 C10 -2.8(3) . . . . ?
C1 N2 C2 O2 178.95(17) . . . . ?
C1 N2 C2 C3 -1.10(19) . . . . ?
C1 N1 C3 C4 -117.29(17) . . . . ?
C1 N1 C3 C2 -0.71(19) . . . . ?
C1 N1 C3 C4A 115.14(17) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C11 C16 C15 C14 -1.0(3) . . . . ?
O14A N14 C14 C13 178.99(19) . . . . ?
O14A N14 C14 C15 -1.2(3) . . . . ?
C9 C4 C5 C6 2.1(3) . . . . ?
C5A C4A C9A C8A 0.8(3) . . . . ?
C5A C6A C7A C8A -0.4(3) . . . . ?
C9A C4A C5A C6A -1.1(3) . . . . ?
C5 C4 C9 C8 -2.2(3) . . . . ?
O14B N14 C14 C13 0.5(3) . . . . ?
O14B N14 C14 C15 -179.6(2) . . . . ?
C6A C7A C8A C9A 0.1(3) . . . . ?
C15 C14 C13 C12 0.6(3) . . . . ?
C8 C7 C6 C5 -1.7(3) . . . . ?
C6 C7 C8 C9 1.7(3) . . . . ?

_olex2_date_sample_data_collection 2019-05-14
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.224
_oxdiff_exptl_absorpt_empirical_full_min 0.525
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_521
_database_code_depnum_ccdc_archive 'CCDC 2011732'
loop_
_audit_author_name
_audit_author_address
'Boris Shivachev'
;Institute of Mineralogy and Crystallography
Bulgaria
;
_audit_update_record             
;
2020-06-23 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;
_audit_creation_date             2019-07-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 N4 O2'
_chemical_formula_sum            'C21 H16 N4 O2'
_chemical_formula_weight         356.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H30 N4 O4'
_chemical_oxdiff_usercomment     'SB4-Ph Petia '
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.3125(6)
_cell_length_b                   8.4276(3)
_cell_length_c                   27.2914(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.355(4)
_cell_angle_gamma                90
_cell_volume                     3618.0(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4193
_cell_measurement_temperature    290
_cell_measurement_theta_max      26.4090
_cell_measurement_theta_min      3.2990
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.854
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            12845
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.471
_diffrn_reflns_theta_min         2.976
_diffrn_ambient_temperature      290
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3974
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.854
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     41.00  72.00   1.00   20.00    --    7.52  57.00-180.00   31
  2  ω     21.00  82.00   1.00   20.00    --    7.52  38.00 -30.00   61
  3  ω     -2.00  84.00   1.00   20.00    --    7.52  77.00  30.00   86
  4  ω    -17.00   9.00   1.00   20.00    --   -8.15 -99.00   0.00   26
  5  ω     -8.00  23.00   1.00   20.00    --   -8.15 -77.00 -60.00   31
  6  ω    -12.00  27.00   1.00   20.00    --   -8.15 -99.00  30.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0389154000
_diffrn_orient_matrix_UB_12      0.0102132000
_diffrn_orient_matrix_UB_13      0.0188934000
_diffrn_orient_matrix_UB_21      -0.0227323000
_diffrn_orient_matrix_UB_22      0.0207914000
_diffrn_orient_matrix_UB_23      0.0179062000
_diffrn_orient_matrix_UB_31      -0.0009441000
_diffrn_orient_matrix_UB_32      -0.0809503000
_diffrn_orient_matrix_UB_33      0.0069731000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2743
_reflns_number_total             3912
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3912
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+2.5772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1320
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C15(H15), C9(H9), C12(H12), C14(H14), C5(H5), C9A(H9A), C13(H13),
 C8(H8), C5A(H5A), C7(H7), C8A(H8A), C6(H6), C7A(H7A), C6A(H6A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
N3 N 0.58421(9) 0.23245(19) 0.67100(6) 0.0431(4) Uani 1 1 d . . . . .
N4 N 0.72056(10) 0.01981(19) 0.77078(6) 0.0466(4) Uani 1 1 d . . . . .
O2 O 0.48555(9) 0.32389(17) 0.57616(5) 0.0503(4) Uani 1 1 d . . . . .
N2 N 0.51076(9) 0.32229(18) 0.66340(5) 0.0394(4) Uani 1 1 d . . . . .
O1 O 0.49226(8) 0.36125(17) 0.74488(5) 0.0491(4) Uani 1 1 d . . . . .
N1 N 0.40768(10) 0.4791(2) 0.67355(5) 0.0428(4) Uani 1 1 d . . . . .
C1 C 0.47116(11) 0.3862(2) 0.69951(7) 0.0389(4) Uani 1 1 d . . . . .
C3 C 0.39484(11) 0.4740(2) 0.61850(6) 0.0389(4) Uani 1 1 d . . . . .
C2 C 0.46779(11) 0.3644(2) 0.61428(7) 0.0379(4) Uani 1 1 d . . . . .
C11 C 0.69483(11) 0.0802(2) 0.72387(7) 0.0425(4) Uani 1 1 d . . . . .
C10 C 0.61679(12) 0.1756(2) 0.71464(7) 0.0471(5) Uani 1 1 d . . . . .
H10 H 0.591446 0.193996 0.740880 0.057 Uiso 1 1 calc R . . . .
C4 C 0.40895(12) 0.6350(2) 0.59633(7) 0.0435(4) Uani 1 1 d . . . . .
C4A C 0.30717(12) 0.4038(2) 0.59399(7) 0.0454(5) Uani 1 1 d . . . . .
C15 C 0.79155(12) -0.0675(2) 0.78228(8) 0.0519(5) Uani 1 1 d . . . . .
H15 H 0.809588 -0.110611 0.814735 0.062 Uiso 1 1 calc R . . . .
C9 C 0.38642(15) 0.6550(3) 0.54433(8) 0.0599(6) Uani 1 1 d . . . . .
H9 H 0.360090 0.572444 0.523402 0.072 Uiso 1 1 calc R . . . .
C12 C 0.73921(15) 0.0557(3) 0.68797(9) 0.0633(6) Uani 1 1 d . . . . .
H12 H 0.720108 0.098623 0.655550 0.076 Uiso 1 1 calc R . . . .
C14 C 0.83878(13) -0.0965(3) 0.74891(9) 0.0592(6) Uani 1 1 d . . . . .
H14 H 0.887900 -0.157652 0.758453 0.071 Uiso 1 1 calc R . . . .
C5 C 0.44810(14) 0.7588(3) 0.62638(8) 0.0578(6) Uani 1 1 d . . . . .
H5 H 0.464329 0.747425 0.661528 0.069 Uiso 1 1 calc R . . . .
C9A C 0.23633(14) 0.4966(3) 0.59148(9) 0.0688(7) Uani 1 1 d . . . . .
H9A H 0.243041 0.601324 0.602597 0.083 Uiso 1 1 calc R . . . .
C13 C 0.81258(15) -0.0340(3) 0.70121(10) 0.0725(7) Uani 1 1 d . . . . .
H13 H 0.843909 -0.051664 0.677783 0.087 Uiso 1 1 calc R . . . .
C8 C 0.40253(17) 0.7966(3) 0.52293(9) 0.0708(7) Uani 1 1 d . . . . .
H8 H 0.387435 0.808116 0.487786 0.085 Uiso 1 1 calc R . . . .
C5A C 0.29602(15) 0.2498(3) 0.57702(9) 0.0690(7) Uani 1 1 d . . . . .
H5A H 0.342941 0.185909 0.578070 0.083 Uiso 1 1 calc R . . . .
C7 C 0.44048(16) 0.9193(3) 0.55315(10) 0.0687(7) Uani 1 1 d . . . . .
H7 H 0.450533 1.014962 0.538776 0.082 Uiso 1 1 calc R . . . .
C8A C 0.15564(16) 0.4351(5) 0.57261(10) 0.0884(10) Uani 1 1 d . . . . .
H8A H 0.108300 0.498320 0.571075 0.106 Uiso 1 1 calc R . . . .
C6 C 0.46348(17) 0.9004(3) 0.60456(10) 0.0710(7) Uani 1 1 d . . . . .
H6 H 0.489806 0.983460 0.625245 0.085 Uiso 1 1 calc R . . . .
C7A C 0.14532(19) 0.2815(6) 0.55619(11) 0.1014(12) Uani 1 1 d . . . . .
H7A H 0.091000 0.239942 0.543589 0.122 Uiso 1 1 calc R . . . .
C6A C 0.2144(2) 0.1899(4) 0.55830(12) 0.1013(10) Uani 1 1 d . . . . .
H6A H 0.207113 0.085402 0.547052 0.122 Uiso 1 1 calc R . . . .
H1 H 0.3634(14) 0.505(2) 0.6864(8) 0.055(6) Uiso 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
N3 N2 1.386(2) . ?
N3 C10 1.263(2) . ?
N4 C11 1.338(2) . ?
N4 C15 1.337(2) . ?
O2 C2 1.201(2) . ?
N2 C1 1.420(2) . ?
N2 C2 1.385(2) . ?
O1 C1 1.213(2) . ?
N1 C1 1.341(2) . ?
N1 C3 1.461(2) . ?
N1 H1 0.91(2) . ?
C3 C2 1.535(3) . ?
C3 C4 1.527(3) . ?
C3 C4A 1.529(3) . ?
C11 C10 1.470(3) . ?
C11 C12 1.379(3) . ?
C10 H10 0.9300 . ?
C4 C9 1.379(3) . ?
C4 C5 1.376(3) . ?
C4A C9A 1.382(3) . ?
C4A C5A 1.374(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.362(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.384(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.364(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(3) . ?
C9A H9A 0.9300 . ?
C9A C8A 1.381(4) . ?
C13 H13 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.365(3) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.388(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.362(4) . ?
C8A H8A 0.9300 . ?
C8A C7A 1.365(5) . ?
C6 H6 0.9300 . ?
C7A H7A 0.9300 . ?
C7A C6A 1.355(5) . ?
C6A H6A 0.9300 . ?

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
C10 N3 N2 118.68(16) . . ?
C15 N4 C11 117.83(17) . . ?
N3 N2 C1 129.63(14) . . ?
C2 N2 N3 118.75(14) . . ?
C2 N2 C1 111.59(14) . . ?
C1 N1 C3 113.97(15) . . ?
C1 N1 H1 121.2(13) . . ?
C3 N1 H1 119.4(13) . . ?
O1 C1 N2 125.77(17) . . ?
O1 C1 N1 127.69(17) . . ?
N1 C1 N2 106.54(15) . . ?
N1 C3 C2 101.07(13) . . ?
N1 C3 C4 112.68(15) . . ?
N1 C3 C4A 108.92(15) . . ?
C4 C3 C2 107.67(14) . . ?
C4 C3 C4A 113.08(15) . . ?
C4A C3 C2 112.85(15) . . ?
O2 C2 N2 126.11(17) . . ?
O2 C2 C3 127.30(16) . . ?
N2 C2 C3 106.58(14) . . ?
N4 C11 C10 114.21(17) . . ?
N4 C11 C12 122.14(18) . . ?
C12 C11 C10 123.64(18) . . ?
N3 C10 C11 119.89(18) . . ?
N3 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C9 C4 C3 119.32(17) . . ?
C5 C4 C3 122.16(17) . . ?
C5 C4 C9 118.41(19) . . ?
C9A C4A C3 118.4(2) . . ?
C5A C4A C3 122.57(19) . . ?
C5A C4A C9A 118.9(2) . . ?
N4 C15 H15 118.3 . . ?
N4 C15 C14 123.3(2) . . ?
C14 C15 H15 118.3 . . ?
C4 C9 H9 119.6 . . ?
C4 C9 C8 120.8(2) . . ?
C8 C9 H9 119.6 . . ?
C11 C12 H12 120.7 . . ?
C11 C12 C13 118.6(2) . . ?
C13 C12 H12 120.7 . . ?
C15 C14 H14 120.7 . . ?
C15 C14 C13 118.6(2) . . ?
C13 C14 H14 120.7 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4A C9A H9A 119.7 . . ?
C8A C9A C4A 120.5(3) . . ?
C8A C9A H9A 119.7 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.3 . . ?
C9 C8 H8 119.8 . . ?
C7 C8 C9 120.3(2) . . ?
C7 C8 H8 119.8 . . ?
C4A C5A H5A 120.1 . . ?
C4A C5A C6A 119.7(3) . . ?
C6A C5A H5A 120.1 . . ?
C8 C7 H7 120.3 . . ?
C6 C7 C8 119.4(2) . . ?
C6 C7 H7 120.3 . . ?
C9A C8A H8A 120.0 . . ?
C7A C8A C9A 120.1(3) . . ?
C7A C8A H8A 120.0 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 H6 119.6 . . ?
C8A C7A H7A 120.1 . . ?
C6A C7A C8A 119.8(3) . . ?
C6A C7A H7A 120.1 . . ?
C5A C6A H6A 119.5 . . ?
C7A C6A C5A 121.0(3) . . ?
C7A C6A H6A 119.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 O1 0.93 2.17 2.854(2) 129.5 .
C14 H14 O1 0.93 2.51 3.377(3) 154.7 6_655

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 N2 C1 O1 -6.5(3) . . . . ?
N3 N2 C1 N1 172.84(16) . . . . ?
N3 N2 C2 O2 4.0(3) . . . . ?
N3 N2 C2 C3 -175.15(14) . . . . ?
N4 C11 C10 N3 -176.68(17) . . . . ?
N4 C11 C12 C13 -0.1(3) . . . . ?
N4 C15 C14 C13 -0.2(3) . . . . ?
N2 N3 C10 C11 -179.82(16) . . . . ?
N1 C3 C2 O2 -179.05(18) . . . . ?
N1 C3 C2 N2 0.04(18) . . . . ?
N1 C3 C4 C9 -169.93(18) . . . . ?
N1 C3 C4 C5 14.0(3) . . . . ?
N1 C3 C4A C9A 74.0(2) . . . . ?
N1 C3 C4A C5A -102.3(2) . . . . ?
C1 N2 C2 O2 -177.93(17) . . . . ?
C1 N2 C2 C3 2.97(19) . . . . ?
C1 N1 C3 C2 -3.3(2) . . . . ?
C1 N1 C3 C4 -117.92(17) . . . . ?
C1 N1 C3 C4A 115.76(18) . . . . ?
C3 N1 C1 N2 5.1(2) . . . . ?
C3 N1 C1 O1 -175.50(18) . . . . ?
C3 C4 C9 C8 -176.5(2) . . . . ?
C3 C4 C5 C6 176.8(2) . . . . ?
C3 C4A C9A C8A -175.9(2) . . . . ?
C3 C4A C5A C6A 175.6(2) . . . . ?
C2 N2 C1 O1 175.61(17) . . . . ?
C2 N2 C1 N1 -5.0(2) . . . . ?
C2 C3 C4 C9 79.5(2) . . . . ?
C2 C3 C4 C5 -96.6(2) . . . . ?
C2 C3 C4A C9A -174.63(18) . . . . ?
C2 C3 C4A C5A 9.1(3) . . . . ?
C11 N4 C15 C14 0.5(3) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C10 N3 N2 C1 12.0(3) . . . . ?
C10 N3 N2 C2 -170.31(17) . . . . ?
C10 C11 C12 C13 178.9(2) . . . . ?
C4 C3 C2 O2 -60.7(2) . . . . ?
C4 C3 C2 N2 118.38(15) . . . . ?
C4 C3 C4A C9A -52.1(2) . . . . ?
C4 C3 C4A C5A 131.6(2) . . . . ?
C4 C9 C8 C7 -0.6(4) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C4A C3 C2 O2 64.8(2) . . . . ?
C4A C3 C2 N2 -116.12(16) . . . . ?
C4A C3 C4 C9 -45.9(2) . . . . ?
C4A C3 C4 C5 138.01(19) . . . . ?
C4A C9A C8A C7A -0.1(4) . . . . ?
C4A C5A C6A C7A 0.4(4) . . . . ?
C15 N4 C11 C10 -179.50(17) . . . . ?
C15 N4 C11 C12 -0.4(3) . . . . ?
C15 C14 C13 C12 -0.3(4) . . . . ?
C9 C4 C5 C6 0.6(3) . . . . ?
C9 C8 C7 C6 1.0(4) . . . . ?
C12 C11 C10 N3 4.2(3) . . . . ?
C5 C4 C9 C8 -0.2(3) . . . . ?
C9A C4A C5A C6A -0.7(4) . . . . ?
C9A C8A C7A C6A -0.2(5) . . . . ?
C8 C7 C6 C5 -0.6(4) . . . . ?
C5A C4A C9A C8A 0.5(3) . . . . ?
C8A C7A C6A C5A 0.1(5) . . . . ?

_olex2_date_sample_data_collection 2019-05-14
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.354
_oxdiff_exptl_absorpt_empirical_full_min 0.633
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_531_2_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2011733'
loop_
_audit_author_name
_audit_author_address
'Boris Shivachev'
;Institute of Mineralogy and Crystallography
Bulgaria
;
_audit_update_record             
;
2020-06-23 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;
_audit_creation_date             2020-06-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 N3 O3'
_chemical_formula_sum            'C22 H17 N3 O3'
_chemical_formula_weight         371.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 N3 O2 H20'
_chemical_oxdiff_usercomment     'Petyia SB2 Ph'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5374(8)
_cell_length_b                   10.4625(17)
_cell_length_c                   11.6521(17)
_cell_angle_alpha                107.718(14)
_cell_angle_beta                 96.228(10)
_cell_angle_gamma                106.521(11)
_cell_volume                     928.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1733
_cell_measurement_temperature    290
_cell_measurement_theta_max      26.7520
_cell_measurement_theta_min      3.4490
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0886
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.803
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5865
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.560
_diffrn_reflns_theta_min         2.737
_diffrn_ambient_temperature      290
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3974
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.803
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  82.00   1.00   90.00    --    7.68  38.00 -90.00   96
  2  ω    -17.00  78.00   1.00   90.00    --    7.68  77.00   0.00   95
  3  ω    -67.00  39.00   1.00   90.00    --    7.68 -77.00 120.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0755735000
_diffrn_orient_matrix_UB_12      -0.0015586000
_diffrn_orient_matrix_UB_13      0.0204553000
_diffrn_orient_matrix_UB_21      -0.0180163000
_diffrn_orient_matrix_UB_22      0.0375648000
_diffrn_orient_matrix_UB_23      -0.0382671000
_diffrn_orient_matrix_UB_31      -0.0428101000
_diffrn_orient_matrix_UB_32      -0.0655187000
_diffrn_orient_matrix_UB_33      -0.0489501000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2745
_reflns_number_total             5865
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5865
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1352
_refine_ls_R_factor_gt           0.0618
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0896P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.1927
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7129(16)
 0.2871(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O16-H16
 1.01 with sigma of 0.002
4.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C5(H5), C9(H9), C8(H8), C7(H7), C9A(H9A), C5A(H5A), C12(H12),
 C13(H13), C6(H6), C8A(H8A), C15(H15), C14(H14), C6A(H6A), C7A(H7A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.0382(3) 0.5742(3) 0.3765(2) 0.0506(7) Uani 1 1 d . . . . .
N3 N 0.1570(4) 0.5088(3) 0.1652(3) 0.0451(8) Uani 1 1 d . . . . .
N2 N 0.1117(4) 0.4124(3) 0.2252(3) 0.0438(8) Uani 1 1 d . . . . .
N1 N 0.0472(4) 0.3607(3) 0.3879(3) 0.0454(8) Uani 1 1 d . . . . .
O2 O 0.1702(4) 0.2131(3) 0.1147(2) 0.0632(8) Uani 1 1 d . . . . .
O16 O 0.2001(5) 0.7633(3) 0.1599(3) 0.0859(11) Uani 1 1 d D . . . .
C1 C 0.0608(4) 0.4612(4) 0.3383(3) 0.0407(9) Uani 1 1 d . . . . .
C4A C 0.2556(5) 0.2348(4) 0.3805(3) 0.0455(10) Uani 1 1 d . . . . .
C2 C 0.1281(4) 0.2800(4) 0.2035(3) 0.0444(9) Uani 1 1 d . . . . .
C4 C -0.0488(4) 0.1007(4) 0.2892(3) 0.0390(9) Uani 1 1 d . . . . .
C10 C 0.1986(5) 0.4728(4) 0.0615(4) 0.0553(11) Uani 1 1 d . . . . .
H10 H 0.194895 0.379636 0.023254 0.066 Uiso 1 1 calc R U . . .
C11 C 0.2517(5) 0.5769(4) 0.0034(3) 0.0479(10) Uani 1 1 d . . . . .
C3 C 0.0913(4) 0.2398(4) 0.3166(3) 0.0421(9) Uani 1 1 d . . . . .
C5 C -0.1306(5) 0.0070(4) 0.1712(4) 0.0542(11) Uani 1 1 d . . . . .
H5 H -0.097564 0.026444 0.103143 0.065 Uiso 1 1 calc R U . . .
C9 C -0.0980(4) 0.0667(4) 0.3879(3) 0.0486(10) Uani 1 1 d . . . . .
H9 H -0.042390 0.127370 0.467571 0.058 Uiso 1 1 calc R U . . .
C16 C 0.2517(5) 0.7155(4) 0.0534(4) 0.0549(11) Uani 1 1 d . . . . .
C8 C -0.2282(5) -0.0557(4) 0.3706(4) 0.0570(11) Uani 1 1 d . . . . .
H8 H -0.260654 -0.076476 0.438360 0.068 Uiso 1 1 calc R U . . .
C7 C -0.3093(5) -0.1462(5) 0.2540(4) 0.0593(12) Uani 1 1 d . . . . .
H7 H -0.397241 -0.228671 0.242288 0.071 Uiso 1 1 calc R U . . .
C9A C 0.3516(5) 0.3384(4) 0.4904(4) 0.0581(11) Uani 1 1 d . . . . .
H9A H 0.316994 0.414287 0.528949 0.070 Uiso 1 1 calc R U . . .
C5A C 0.3100(5) 0.1215(5) 0.3256(4) 0.0599(12) Uani 1 1 d . . . . .
H5A H 0.245560 0.049672 0.252618 0.072 Uiso 1 1 calc R U . . .
C12 C 0.3049(6) 0.5393(5) -0.1074(4) 0.0749(14) Uani 1 1 d . . . . .
H12 H 0.304910 0.446779 -0.142878 0.090 Uiso 1 1 calc R U . . .
C13 C 0.3570(6) 0.6349(6) -0.1653(4) 0.0758(14) Uani 1 1 d . . . . .
H13 H 0.392906 0.607637 -0.238648 0.091 Uiso 1 1 calc R U . . .
C6 C -0.2616(5) -0.1159(5) 0.1546(4) 0.0640(12) Uani 1 1 d . . . . .
H6 H -0.317255 -0.177863 0.075247 0.077 Uiso 1 1 calc R U . . .
C8A C 0.4983(6) 0.3291(5) 0.5428(5) 0.0733(14) Uani 1 1 d . . . . .
H8A H 0.562069 0.398830 0.617131 0.088 Uiso 1 1 calc R U . . .
C15 C 0.3040(6) 0.8106(5) -0.0068(4) 0.0740(13) Uani 1 1 d . . . . .
H15 H 0.303729 0.903382 0.026664 0.089 Uiso 1 1 calc R U . . .
C14 C 0.3558(6) 0.7693(6) -0.1149(4) 0.0738(14) Uani 1 1 d . . . . .
H14 H 0.390674 0.834274 -0.154163 0.089 Uiso 1 1 calc R U . . .
C6A C 0.4573(6) 0.1151(6) 0.3785(5) 0.0747(14) Uani 1 1 d . . . . .
H6A H 0.493284 0.039976 0.340223 0.090 Uiso 1 1 calc R U . . .
C7A C 0.5521(6) 0.2181(6) 0.4868(6) 0.0788(15) Uani 1 1 d . . . . .
H7A H 0.652164 0.213186 0.522403 0.095 Uiso 1 1 calc R U . . .
H1 H 0.022(4) 0.373(4) 0.464(3) 0.051(11) Uiso 1 1 d . . . . .
H16 H 0.167(8) 0.673(3) 0.180(5) 0.15(2) Uiso 1 1 d 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
O1 C1 1.209(4) . ?
N3 N2 1.387(4) . ?
N3 C10 1.273(5) . ?
N2 C1 1.423(4) . ?
N2 C2 1.380(5) . ?
N1 C1 1.330(5) . ?
N1 C3 1.459(4) . ?
N1 H1 0.92(4) . ?
O2 C2 1.214(4) . ?
O16 C16 1.359(5) . ?
O16 H16 1.010(3) . ?
C4A C3 1.537(5) . ?
C4A C9A 1.382(5) . ?
C4A C5A 1.396(5) . ?
C2 C3 1.538(5) . ?
C4 C3 1.515(5) . ?
C4 C5 1.386(5) . ?
C4 C9 1.376(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.444(5) . ?
C11 C16 1.389(6) . ?
C11 C12 1.394(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(6) . ?
C9 H9 0.9300 . ?
C9 C8 1.379(5) . ?
C16 C15 1.386(6) . ?
C8 H8 0.9300 . ?
C8 C7 1.365(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.364(6) . ?
C9A H9A 0.9300 . ?
C9A C8A 1.375(6) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.367(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.370(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.352(6) . ?
C6 H6 0.9300 . ?
C8A H8A 0.9300 . ?
C8A C7A 1.376(7) . ?
C15 H15 0.9300 . ?
C15 C14 1.366(6) . ?
C14 H14 0.9300 . ?
C6A H6A 0.9300 . ?
C6A C7A 1.365(6) . ?
C7A H7A 0.9300 . ?

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
C10 N3 N2 121.1(3) . . ?
N3 N2 C1 116.8(3) . . ?
C2 N2 N3 130.7(3) . . ?
C2 N2 C1 111.8(3) . . ?
C1 N1 C3 114.3(3) . . ?
C1 N1 H1 121(2) . . ?
C3 N1 H1 124(2) . . ?
C16 O16 H16 100(4) . . ?
O1 C1 N2 123.7(3) . . ?
O1 C1 N1 129.8(3) . . ?
N1 C1 N2 106.5(3) . . ?
C9A C4A C3 122.5(4) . . ?
C9A C4A C5A 118.6(4) . . ?
C5A C4A C3 118.9(3) . . ?
N2 C2 C3 106.2(3) . . ?
O2 C2 N2 126.1(3) . . ?
O2 C2 C3 127.7(4) . . ?
C5 C4 C3 124.0(3) . . ?
C9 C4 C3 117.6(3) . . ?
C9 C4 C5 118.4(3) . . ?
N3 C10 H10 120.0 . . ?
N3 C10 C11 119.9(4) . . ?
C11 C10 H10 120.0 . . ?
C16 C11 C10 122.4(4) . . ?
C16 C11 C12 117.7(4) . . ?
C12 C11 C10 119.9(4) . . ?
N1 C3 C4A 112.4(3) . . ?
N1 C3 C2 101.1(3) . . ?
N1 C3 C4 111.1(3) . . ?
C4A C3 C2 106.4(3) . . ?
C4 C3 C4A 110.3(3) . . ?
C4 C3 C2 115.3(3) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C9 H9 119.4 . . ?
C4 C9 C8 121.2(3) . . ?
C8 C9 H9 119.4 . . ?
O16 C16 C11 122.7(4) . . ?
O16 C16 C15 117.5(4) . . ?
C15 C16 C11 119.7(4) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 C9 119.9(4) . . ?
C7 C8 H8 120.1 . . ?
C8 C7 H7 119.9 . . ?
C6 C7 C8 120.1(4) . . ?
C6 C7 H7 119.9 . . ?
C4A C9A H9A 120.0 . . ?
C8A C9A C4A 120.0(4) . . ?
C8A C9A H9A 120.0 . . ?
C4A C5A H5A 119.8 . . ?
C6A C5A C4A 120.5(4) . . ?
C6A C5A H5A 119.8 . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.8(4) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.5(4) . . ?
C14 C13 H13 120.3 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.3(4) . . ?
C7 C6 H6 119.9 . . ?
C9A C8A H8A 119.6 . . ?
C9A C8A C7A 120.8(4) . . ?
C7A C8A H8A 119.6 . . ?
C16 C15 H15 119.7 . . ?
C14 C15 C16 120.6(5) . . ?
C14 C15 H15 119.7 . . ?
C13 C14 C15 120.7(4) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C5A C6A H6A 119.7 . . ?
C7A C6A C5A 120.6(5) . . ?
C7A C6A H6A 119.7 . . ?
C8A C7A H7A 120.3 . . ?
C6A C7A C8A 119.4(5) . . ?
C6A C7A H7A 120.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H10 O2 0.93 2.28 2.917(5) 125.5 . yes
N1 H1 O1 0.92(4) 1.94(4) 2.847(4) 170(3) 2_566 yes
O16 H16 N3 1.010(3) 1.65(3) 2.603(4) 155(6) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 N2 C1 O1 8.2(5) . . . . ?
N3 N2 C1 N1 -171.2(3) . . . . ?
N3 N2 C2 O2 -9.4(6) . . . . ?
N3 N2 C2 C3 167.8(3) . . . . ?
N3 C10 C11 C16 -3.3(6) . . . . ?
N3 C10 C11 C12 177.0(4) . . . . ?
N2 N3 C10 C11 -177.5(3) . . . . ?
N2 C2 C3 N1 3.2(3) . . . . ?
N2 C2 C3 C4A -114.3(3) . . . . ?
N2 C2 C3 C4 123.1(3) . . . . ?
O2 C2 C3 N1 -179.6(4) . . . . ?
O2 C2 C3 C4A 62.8(5) . . . . ?
O2 C2 C3 C4 -59.7(5) . . . . ?
O16 C16 C15 C14 -179.4(4) . . . . ?
C1 N2 C2 O2 -179.8(3) . . . . ?
C1 N2 C2 C3 -2.6(4) . . . . ?
C1 N1 C3 C4A 110.0(3) . . . . ?
C1 N1 C3 C2 -3.1(4) . . . . ?
C1 N1 C3 C4 -125.9(3) . . . . ?
C4A C9A C8A C7A 0.4(7) . . . . ?
C4A C5A C6A C7A 1.2(7) . . . . ?
C2 N2 C1 O1 -179.9(3) . . . . ?
C2 N2 C1 N1 0.7(4) . . . . ?
C4 C5 C6 C7 -0.9(6) . . . . ?
C4 C9 C8 C7 0.7(6) . . . . ?
C10 N3 N2 C1 -177.6(3) . . . . ?
C10 N3 N2 C2 12.4(6) . . . . ?
C10 C11 C16 O16 -0.8(6) . . . . ?
C10 C11 C16 C15 -179.9(4) . . . . ?
C10 C11 C12 C13 -179.7(4) . . . . ?
C11 C16 C15 C14 -0.1(7) . . . . ?
C11 C12 C13 C14 -0.6(8) . . . . ?
C3 N1 C1 O1 -177.7(3) . . . . ?
C3 N1 C1 N2 1.7(4) . . . . ?
C3 C4A C9A C8A -179.4(4) . . . . ?
C3 C4A C5A C6A 178.6(4) . . . . ?
C3 C4 C5 C6 -177.7(4) . . . . ?
C3 C4 C9 C8 177.8(3) . . . . ?
C5 C4 C3 N1 120.0(4) . . . . ?
C5 C4 C3 C4A -114.7(4) . . . . ?
C5 C4 C3 C2 5.8(5) . . . . ?
C5 C4 C9 C8 -1.6(6) . . . . ?
C9 C4 C3 N1 -59.4(4) . . . . ?
C9 C4 C3 C4A 65.9(4) . . . . ?
C9 C4 C3 C2 -173.6(3) . . . . ?
C9 C4 C5 C6 1.7(6) . . . . ?
C9 C8 C7 C6 0.1(6) . . . . ?
C16 C11 C12 C13 0.6(7) . . . . ?
C16 C15 C14 C13 0.1(8) . . . . ?
C8 C7 C6 C5 0.0(7) . . . . ?
C9A C4A C3 N1 -2.7(5) . . . . ?
C9A C4A C3 C2 107.1(4) . . . . ?
C9A C4A C3 C4 -127.2(4) . . . . ?
C9A C4A C5A C6A -1.5(6) . . . . ?
C9A C8A C7A C6A -0.7(7) . . . . ?
C5A C4A C3 N1 177.2(3) . . . . ?
C5A C4A C3 C2 -73.0(4) . . . . ?
C5A C4A C3 C4 52.7(4) . . . . ?
C5A C4A C9A C8A 0.7(6) . . . . ?
C5A C6A C7A C8A -0.1(7) . . . . ?
C12 C11 C16 O16 179.0(4) . . . . ?
C12 C11 C16 C15 -0.2(6) . . . . ?
C12 C13 C14 C15 0.3(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.418
_oxdiff_exptl_absorpt_empirical_full_min 0.750
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.7129(16) 3372 3921 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.2871(16) 3407 3921 nmt -1.0029 -0.0016 0.0024 0.3101 0.2207 -0.7779 -0.3100
-1.2172 -0.2251

_twin_special_details            
;
Component 2 rotated by 179.9778° 
 around [-0.00 -0.71 0.71] (reciprocal) or [-0.21 -0.82 0.53] (direct)
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
