# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_nz-578
_database_code_depnum_ccdc_archive 'CCDC 2132435'
loop_
_audit_author_name
_audit_author_address
'Peng xichao'
;Ji Nan University
China
;
_audit_update_record             
;
2022-01-11 deposited with the CCDC.	2022-05-18 downloaded from the CCDC.
;
_audit_creation_date             2022-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.4(C30 H21 N O3)'
_chemical_formula_sum            'C12 H8.40 N0.40 O1.20'
_chemical_formula_weight         177.39
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
H H 0.0000 0.0000 '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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   14.6391(3)
_cell_length_b                   15.2080(3)
_cell_length_c                   20.3989(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4541.44(16)
_cell_formula_units_Z            20
_cell_measurement_reflns_used    8243
_cell_measurement_temperature    297.93(10)
_cell_measurement_theta_max      71.5760
_cell_measurement_theta_min      3.6350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light white'
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18571
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.079
_diffrn_reflns_theta_min         3.625
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.93(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00  88.00   0.50    0.84    --    0.00  38.00-180.00   80
  2  ω    -12.00  22.00   0.50    0.84    --    0.00  38.00-180.00   68
  3  ω     43.00  69.00   0.50    0.84    --    0.00  38.00  30.00   52
  4  ω    -80.00 -23.00   0.50    0.84    --    0.00 -57.00  90.00  114
  5  ω     31.00  58.00   0.50    0.84    --    0.00  19.00 -60.00   54
  6  ω    154.00 182.00   0.50    3.37    --   95.20  30.00-150.00   56
  7  ω     97.00 135.00   0.50    3.37    --   95.20  30.00-150.00   76
  8  ω     41.00 115.00   0.50    3.37    --   95.20 -61.00 -30.00  148
  9  ω     12.00  37.00   0.50    3.37    --   95.20 -61.00 -30.00   50
 10  ω     66.00 135.00   0.50    3.37    --   95.20  77.00-150.00  138
 11  ω     24.00 174.00   0.50    3.37    --   95.20   0.00   0.00  300
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0326937000
_diffrn_orient_matrix_UB_12      -0.0691313000
_diffrn_orient_matrix_UB_13      0.0500470000
_diffrn_orient_matrix_UB_21      -0.0529784000
_diffrn_orient_matrix_UB_22      0.0717754000
_diffrn_orient_matrix_UB_23      0.0373317000
_diffrn_orient_matrix_UB_31      -0.0848298000
_diffrn_orient_matrix_UB_32      -0.0182571000
_diffrn_orient_matrix_UB_33      -0.0424888000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    0.895
_reflns_Friedel_fraction_max     0.830
_reflns_number_gt                7109
_reflns_number_total             8411
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 2459 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.42(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     615
_refine_ls_number_reflns         8411
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.048
_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)+(0.0599P)²+0.3914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1244
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C26(H26), C27(H27), C28(H28),
  C29(H29), C30(H30), C34(H34), C35(H35), C36(H36), C37(H37), C42(H42),
 C43(H43), C44(H44), C45(H45), C46(H46), C49(H49), C50(H50), C51(H51), C52(H52),
  C56(H56), C57(H57), C58(H58), C59(H59), C60(H60)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 -0.0785(2) 0.2069(3) 0.39712(14) 0.1023(11) Uani 1 1 d . . . . .
O2 O 0.14968(17) 0.32486(17) 0.31920(12) 0.0708(7) Uani 1 1 d . . . . .
O3 O 0.33938(14) 0.10062(15) 0.25721(10) 0.0543(5) Uani 1 1 d . . . . .
N1 N 0.02329(17) 0.23232(17) 0.31624(13) 0.0543(6) Uani 1 1 d . . . . .
C1 C 0.0327(4) 0.3119(3) 0.4222(2) 0.0995(15) Uani 1 1 d . . . . .
H1A H 0.0950 0.2944 0.4287 0.149 Uiso 1 1 calc GR . . . .
H1B H 0.0020 0.3142 0.4637 0.149 Uiso 1 1 calc GR . . . .
H1C H 0.0311 0.3690 0.4021 0.149 Uiso 1 1 calc GR . . . .
C2 C -0.0130(2) 0.2484(3) 0.37971(17) 0.0662(9) Uani 1 1 d . . . . .
C3 C -0.01212(19) 0.1719(2) 0.27024(16) 0.0518(7) Uani 1 1 d . . . . .
C4 C -0.0907(3) 0.1201(2) 0.2740(2) 0.0719(10) Uani 1 1 d . . . . .
H4 H -0.1281 0.1216 0.3109 0.086 Uiso 1 1 calc R . . . .
C5 C -0.1109(3) 0.0671(3) 0.2220(2) 0.0793(11) Uani 1 1 d . . . . .
H5 H -0.1628 0.0318 0.2241 0.095 Uiso 1 1 calc R . . . .
C6 C -0.0581(3) 0.0638(3) 0.1670(2) 0.0788(11) Uani 1 1 d . . . . .
H6 H -0.0753 0.0279 0.1322 0.095 Uiso 1 1 calc R . . . .
C7 C 0.0237(3) 0.1152(2) 0.16255(19) 0.0655(9) Uani 1 1 d . . . . .
H7 H 0.0615 0.1127 0.1259 0.079 Uiso 1 1 calc R . . . .
C8 C 0.0434(2) 0.16807(19) 0.21466(15) 0.0502(7) Uani 1 1 d . . . . .
C9 C 0.1039(2) 0.2685(2) 0.29195(15) 0.0522(7) Uani 1 1 d . . . . .
C10 C 0.12493(18) 0.22764(19) 0.22364(14) 0.0448(6) Uani 1 1 d . . . . .
C11 C 0.1309(2) 0.30473(19) 0.17540(14) 0.0480(7) Uani 1 1 d . . . . .
C12 C 0.0651(2) 0.3203(2) 0.12816(16) 0.0588(8) Uani 1 1 d . . . . .
H12 H 0.0156 0.2824 0.1240 0.071 Uiso 1 1 calc R . . . .
C13 C 0.0731(3) 0.3924(3) 0.0869(2) 0.0837(12) Uani 1 1 d . . . . .
H13 H 0.0281 0.4033 0.0558 0.100 Uiso 1 1 calc R . . . .
C14 C 0.1466(3) 0.4479(3) 0.0917(2) 0.0887(13) Uani 1 1 d . . . . .
H14 H 0.1512 0.4962 0.0639 0.106 Uiso 1 1 calc R . . . .
C15 C 0.2132(3) 0.4324(3) 0.1372(2) 0.0781(11) Uani 1 1 d . . . . .
H15 H 0.2633 0.4698 0.1401 0.094 Uiso 1 1 calc R . . . .
C16 C 0.2059(2) 0.3609(2) 0.17907(17) 0.0593(8) Uani 1 1 d . . . . .
H16 H 0.2515 0.3503 0.2098 0.071 Uiso 1 1 calc R . . . .
C17 C 0.21453(18) 0.17661(18) 0.22401(14) 0.0437(6) Uani 1 1 d . . . . .
C18 C 0.26972(19) 0.15613(19) 0.16728(14) 0.0464(6) Uani 1 1 d . . . . .
C19 C 0.2641(2) 0.1702(2) 0.09942(15) 0.0563(8) Uani 1 1 d . . . . .
H19 H 0.2156 0.2018 0.0817 0.068 Uiso 1 1 calc R . . . .
C20 C 0.3316(2) 0.1366(3) 0.05947(17) 0.0667(9) Uani 1 1 d . . . . .
H20 H 0.3276 0.1443 0.0143 0.080 Uiso 1 1 calc R . . . .
C21 C 0.4059(3) 0.0911(2) 0.08597(19) 0.0695(10) Uani 1 1 d . . . . .
H21 H 0.4509 0.0699 0.0580 0.083 Uiso 1 1 calc R . . . .
C22 C 0.4142(2) 0.0768(2) 0.15213(18) 0.0604(8) Uani 1 1 d . . . . .
H22 H 0.4637 0.0468 0.1698 0.073 Uiso 1 1 calc R . . . .
C23 C 0.3446(2) 0.1099(2) 0.19100(15) 0.0504(7) Uani 1 1 d . . . . .
C24 C 0.25887(19) 0.1407(2) 0.27632(15) 0.0489(6) Uani 1 1 d . . . . .
C25 C 0.2390(2) 0.1331(2) 0.34707(15) 0.0517(7) Uani 1 1 d . . . . .
C26 C 0.1629(3) 0.0865(2) 0.36838(17) 0.0650(9) Uani 1 1 d . . . . .
H26 H 0.1233 0.0613 0.3381 0.078 Uiso 1 1 calc R . . . .
C27 C 0.1463(3) 0.0778(3) 0.4348(2) 0.0845(12) Uani 1 1 d . . . . .
H27 H 0.0954 0.0468 0.4493 0.101 Uiso 1 1 calc R . . . .
C28 C 0.2053(4) 0.1151(4) 0.47931(19) 0.0942(14) Uani 1 1 d . . . . .
H28 H 0.1943 0.1088 0.5240 0.113 Uiso 1 1 calc R . . . .
C29 C 0.2801(3) 0.1613(3) 0.45843(19) 0.0878(13) Uani 1 1 d . . . . .
H29 H 0.3192 0.1868 0.4889 0.105 Uiso 1 1 calc R . . . .
C30 C 0.2977(3) 0.1701(3) 0.39259(17) 0.0698(10) Uani 1 1 d . . . . .
H30 H 0.3489 0.2010 0.3786 0.084 Uiso 1 1 calc R . . . .
O4 O 0.42581(15) 0.39817(15) 0.24138(10) 0.0571(5) Uani 1 1 d . . . . .
O5 O 0.60485(17) 0.16320(17) 0.19168(12) 0.0726(7) Uani 1 1 d . . . . .
O6 O 0.83972(19) 0.2593(2) 0.10479(13) 0.0844(8) Uani 1 1 d . . . . .
N2 N 0.73646(16) 0.24783(16) 0.18707(12) 0.0493(6) Uani 1 1 d . . . . .
C31 C 0.7142(3) 0.1673(3) 0.08185(19) 0.0920(14) Uani 1 1 d . . . . .
H31A H 0.7139 0.1093 0.1006 0.138 Uiso 1 1 calc GR . . . .
H31B H 0.7403 0.1650 0.0387 0.138 Uiso 1 1 calc GR . . . .
H31C H 0.6527 0.1889 0.0791 0.138 Uiso 1 1 calc GR . . . .
C32 C 0.7696(2) 0.2272(2) 0.12404(16) 0.0604(8) Uani 1 1 d . . . . .
C33 C 0.77633(19) 0.31324(18) 0.22899(15) 0.0472(6) Uani 1 1 d . . . . .
C34 C 0.8569(2) 0.3590(2) 0.22145(19) 0.0623(8) Uani 1 1 d . . . . .
H34 H 0.8953 0.3485 0.1860 0.075 Uiso 1 1 calc R . . . .
C35 C 0.8787(2) 0.4210(2) 0.2685(2) 0.0677(9) Uani 1 1 d . . . . .
H35 H 0.9332 0.4519 0.2647 0.081 Uiso 1 1 calc R . . . .
C36 C 0.8226(2) 0.4381(2) 0.32021(19) 0.0635(9) Uani 1 1 d . . . . .
H36 H 0.8390 0.4803 0.3511 0.076 Uiso 1 1 calc R . . . .
C37 C 0.7411(2) 0.3925(2) 0.32680(16) 0.0534(7) Uani 1 1 d . . . . .
H37 H 0.7016 0.4052 0.3613 0.064 Uiso 1 1 calc R . . . .
C38 C 0.71924(18) 0.32831(18) 0.28174(14) 0.0456(6) Uani 1 1 d . . . . .
C39 C 0.6532(2) 0.2194(2) 0.21398(15) 0.0504(7) Uani 1 1 d . . . . .
C40 C 0.63708(18) 0.26922(19) 0.27931(14) 0.0457(6) Uani 1 1 d . . . . .
C41 C 0.6342(2) 0.20044(19) 0.33471(15) 0.0480(7) Uani 1 1 d . . . . .
C42 C 0.5603(2) 0.1426(2) 0.33807(18) 0.0624(8) Uani 1 1 d . . . . .
H42 H 0.5154 0.1438 0.3058 0.075 Uiso 1 1 calc R . . . .
C43 C 0.5541(3) 0.0831(2) 0.3898(2) 0.0752(11) Uani 1 1 d . . . . .
H43 H 0.5050 0.0445 0.3920 0.090 Uiso 1 1 calc R . . . .
C44 C 0.6205(3) 0.0815(2) 0.4377(2) 0.0756(11) Uani 1 1 d . . . . .
H44 H 0.6155 0.0426 0.4727 0.091 Uiso 1 1 calc R . . . .
C45 C 0.6931(3) 0.1368(2) 0.43356(19) 0.0685(9) Uani 1 1 d . . . . .
H45 H 0.7385 0.1347 0.4654 0.082 Uiso 1 1 calc R . . . .
C46 C 0.7004(2) 0.1964(2) 0.38224(16) 0.0549(7) Uani 1 1 d . . . . .
H46 H 0.7505 0.2339 0.3801 0.066 Uiso 1 1 calc R . . . .
C47 C 0.54821(18) 0.32106(19) 0.27747(14) 0.0454(6) Uani 1 1 d . . . . .
C48 C 0.49257(19) 0.34599(19) 0.33392(15) 0.0463(6) Uani 1 1 d . . . . .
C49 C 0.4978(2) 0.3362(2) 0.40173(16) 0.0545(7) Uani 1 1 d . . . . .
H49 H 0.5460 0.3058 0.4209 0.065 Uiso 1 1 calc R . . . .
C50 C 0.4296(3) 0.3728(2) 0.43990(17) 0.0640(9) Uani 1 1 d . . . . .
H50 H 0.4322 0.3666 0.4852 0.077 Uiso 1 1 calc R . . . .
C51 C 0.3576(3) 0.4185(2) 0.41205(19) 0.0681(9) Uani 1 1 d . . . . .
H51 H 0.3128 0.4425 0.4390 0.082 Uiso 1 1 calc R . . . .
C52 C 0.3509(2) 0.4291(3) 0.34547(18) 0.0653(9) Uani 1 1 d . . . . .
H52 H 0.3025 0.4594 0.3265 0.078 Uiso 1 1 calc R . . . .
C53 C 0.4193(2) 0.3926(2) 0.30826(15) 0.0503(7) Uani 1 1 d . . . . .
C54 C 0.50637(19) 0.3554(2) 0.22439(15) 0.0499(7) Uani 1 1 d . . . . .
C55 C 0.5299(2) 0.3618(2) 0.15459(15) 0.0549(7) Uani 1 1 d . . . . .
C56 C 0.4706(3) 0.3298(3) 0.10703(18) 0.0751(10) Uani 1 1 d . . . . .
H56 H 0.4163 0.3023 0.1188 0.090 Uiso 1 1 calc R . . . .
C57 C 0.4940(4) 0.3397(4) 0.0418(2) 0.1005(16) Uani 1 1 d . . . . .
H57 H 0.4551 0.3189 0.0093 0.121 Uiso 1 1 calc R . . . .
C58 C 0.5752(4) 0.3806(4) 0.0246(2) 0.1054(18) Uani 1 1 d . . . . .
H58 H 0.5905 0.3866 -0.0194 0.126 Uiso 1 1 calc R . . . .
C59 C 0.6326(3) 0.4119(3) 0.0713(2) 0.0892(14) Uani 1 1 d . . . . .
H59 H 0.6870 0.4392 0.0595 0.107 Uiso 1 1 calc R . . . .
C60 C 0.6095(2) 0.4029(3) 0.13644(18) 0.0661(9) Uani 1 1 d . . . . .
H60 H 0.6484 0.4249 0.1686 0.079 Uiso 1 1 calc R . . . .


_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 C2 1.202(4) . ?
O2 C9 1.222(4) . ?
O3 C23 1.360(4) . ?
O3 C24 1.383(3) . ?
N1 C2 1.421(4) . ?
N1 C3 1.412(4) . ?
N1 C9 1.393(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.460(6) . ?
C3 C4 1.396(5) . ?
C3 C8 1.396(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.366(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.363(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.434(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.363(4) . ?
C8 C10 1.510(4) . ?
C9 C10 1.557(4) . ?
C10 C11 1.533(4) . ?
C10 C17 1.524(4) . ?
C11 C12 1.382(4) . ?
C11 C16 1.394(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.387(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.371(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.367(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.445(4) . ?
C17 C24 1.363(4) . ?
C18 C19 1.403(4) . ?
C18 C23 1.390(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.398(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.372(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.385(4) . ?
C24 C25 1.477(4) . ?
C25 C26 1.391(5) . ?
C25 C30 1.384(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.383(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.376(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.369(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.374(5) . ?
C30 H30 0.9300 . ?
O4 C53 1.370(4) . ?
O4 C54 1.391(3) . ?
O5 C39 1.199(4) . ?
O6 C32 1.203(4) . ?
N2 C32 1.410(4) . ?
N2 C33 1.436(4) . ?
N2 C39 1.405(4) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C31 C32 1.493(5) . ?
C33 C34 1.378(4) . ?
C33 C38 1.382(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.383(5) . ?
C35 H35 0.9300 . ?
C35 C36 1.361(5) . ?
C36 H36 0.9300 . ?
C36 C37 1.386(5) . ?
C37 H37 0.9300 . ?
C37 C38 1.379(4) . ?
C38 C40 1.502(4) . ?
C39 C40 1.551(4) . ?
C40 C41 1.540(4) . ?
C40 C47 1.522(4) . ?
C41 C42 1.396(4) . ?
C41 C46 1.372(4) . ?
C42 H42 0.9300 . ?
C42 C43 1.392(5) . ?
C43 H43 0.9300 . ?
C43 C44 1.378(6) . ?
C44 H44 0.9300 . ?
C44 C45 1.359(6) . ?
C45 H45 0.9300 . ?
C45 C46 1.389(5) . ?
C46 H46 0.9300 . ?
C47 C48 1.461(4) . ?
C47 C54 1.349(4) . ?
C48 C49 1.393(4) . ?
C48 C53 1.388(4) . ?
C49 H49 0.9300 . ?
C49 C50 1.383(5) . ?
C50 H50 0.9300 . ?
C50 C51 1.385(5) . ?
C51 H51 0.9300 . ?
C51 C52 1.371(5) . ?
C52 H52 0.9300 . ?
C52 C53 1.374(4) . ?
C54 C55 1.468(4) . ?
C55 C56 1.390(5) . ?
C55 C60 1.373(5) . ?
C56 H56 0.9300 . ?
C56 C57 1.382(6) . ?
C57 H57 0.9300 . ?
C57 C58 1.386(7) . ?
C58 H58 0.9300 . ?
C58 C59 1.356(7) . ?
C59 H59 0.9300 . ?
C59 C60 1.378(5) . ?
C60 H60 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
C23 O3 C24 106.4(2) . . ?
C3 N1 C2 125.5(3) . . ?
C9 N1 C2 124.9(3) . . ?
C9 N1 C3 109.4(3) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 N1 118.5(4) . . ?
O1 C2 C1 122.5(4) . . ?
N1 C2 C1 118.9(3) . . ?
C4 C3 N1 129.3(3) . . ?
C8 C3 N1 110.7(3) . . ?
C8 C3 C4 120.1(3) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 117.9(4) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 118.7 . . ?
C6 C5 C4 122.6(4) . . ?
C6 C5 H5 118.7 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.4(4) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 121.7 . . ?
C8 C7 C6 116.6(4) . . ?
C8 C7 H7 121.7 . . ?
C3 C8 C10 109.7(3) . . ?
C7 C8 C3 122.4(3) . . ?
C7 C8 C10 127.9(3) . . ?
O2 C9 N1 125.5(3) . . ?
O2 C9 C10 125.4(3) . . ?
N1 C9 C10 109.2(3) . . ?
C8 C10 C9 101.0(2) . . ?
C8 C10 C11 115.2(2) . . ?
C8 C10 C17 112.1(2) . . ?
C11 C10 C9 106.3(2) . . ?
C17 C10 C9 111.7(2) . . ?
C17 C10 C11 110.1(2) . . ?
C12 C11 C10 122.6(3) . . ?
C12 C11 C16 118.8(3) . . ?
C16 C11 C10 118.6(3) . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(4) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.0(4) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C10 125.9(3) . . ?
C24 C17 C10 128.2(3) . . ?
C24 C17 C18 105.9(2) . . ?
C19 C18 C17 136.4(3) . . ?
C23 C18 C17 105.8(3) . . ?
C23 C18 C19 117.8(3) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 C18 119.0(3) . . ?
C20 C19 H19 120.5 . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.8(3) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 119.1 . . ?
C22 C21 C20 121.9(3) . . ?
C22 C21 H21 119.1 . . ?
C21 C22 H22 121.9 . . ?
C21 C22 C23 116.1(3) . . ?
C23 C22 H22 121.9 . . ?
O3 C23 C18 110.7(3) . . ?
O3 C23 C22 124.9(3) . . ?
C22 C23 C18 124.4(3) . . ?
O3 C24 C25 114.1(2) . . ?
C17 C24 O3 111.2(3) . . ?
C17 C24 C25 134.6(3) . . ?
C26 C25 C24 120.2(3) . . ?
C30 C25 C24 120.1(3) . . ?
C30 C25 C26 119.7(3) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 C25 119.7(4) . . ?
C27 C26 H26 120.1 . . ?
C26 C27 H27 120.1 . . ?
C28 C27 C26 119.8(4) . . ?
C28 C27 H27 120.1 . . ?
C27 C28 H28 119.7 . . ?
C29 C28 C27 120.6(4) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 119.9 . . ?
C28 C29 C30 120.3(4) . . ?
C30 C29 H29 119.9 . . ?
C25 C30 H30 120.0 . . ?
C29 C30 C25 120.0(4) . . ?
C29 C30 H30 120.0 . . ?
C53 O4 C54 106.2(2) . . ?
C32 N2 C33 123.9(3) . . ?
C39 N2 C32 125.9(3) . . ?
C39 N2 C33 109.5(2) . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
C32 C31 H31C 109.5 . . ?
O6 C32 N2 120.0(3) . . ?
O6 C32 C31 121.6(3) . . ?
N2 C32 C31 118.3(3) . . ?
C34 C33 N2 129.2(3) . . ?
C34 C33 C38 121.4(3) . . ?
C38 C33 N2 109.4(2) . . ?
C33 C34 H34 121.2 . . ?
C33 C34 C35 117.6(3) . . ?
C35 C34 H34 121.2 . . ?
C34 C35 H35 119.0 . . ?
C36 C35 C34 122.0(3) . . ?
C36 C35 H35 119.0 . . ?
C35 C36 H36 120.1 . . ?
C35 C36 C37 119.9(3) . . ?
C37 C36 H36 120.1 . . ?
C36 C37 H37 120.3 . . ?
C38 C37 C36 119.3(3) . . ?
C38 C37 H37 120.3 . . ?
C33 C38 C40 111.1(3) . . ?
C37 C38 C33 119.7(3) . . ?
C37 C38 C40 129.2(3) . . ?
O5 C39 N2 125.7(3) . . ?
O5 C39 C40 125.8(3) . . ?
N2 C39 C40 108.5(2) . . ?
C38 C40 C39 101.5(2) . . ?
C38 C40 C41 113.8(2) . . ?
C38 C40 C47 112.0(2) . . ?
C41 C40 C39 107.6(2) . . ?
C47 C40 C39 111.2(2) . . ?
C47 C40 C41 110.3(2) . . ?
C42 C41 C40 119.0(3) . . ?
C46 C41 C40 122.0(3) . . ?
C46 C41 C42 119.0(3) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 C41 119.8(4) . . ?
C43 C42 H42 120.1 . . ?
C42 C43 H43 119.9 . . ?
C44 C43 C42 120.2(4) . . ?
C44 C43 H43 119.9 . . ?
C43 C44 H44 120.1 . . ?
C45 C44 C43 119.7(4) . . ?
C45 C44 H44 120.1 . . ?
C44 C45 H45 119.6 . . ?
C44 C45 C46 120.7(4) . . ?
C46 C45 H45 119.6 . . ?
C41 C46 C45 120.5(3) . . ?
C41 C46 H46 119.7 . . ?
C45 C46 H46 119.7 . . ?
C48 C47 C40 126.3(3) . . ?
C54 C47 C40 127.5(3) . . ?
C54 C47 C48 106.2(3) . . ?
C49 C48 C47 136.4(3) . . ?
C53 C48 C47 105.4(3) . . ?
C53 C48 C49 118.1(3) . . ?
C48 C49 H49 120.8 . . ?
C50 C49 C48 118.4(3) . . ?
C50 C49 H49 120.8 . . ?
C49 C50 H50 119.3 . . ?
C49 C50 C51 121.4(3) . . ?
C51 C50 H50 119.3 . . ?
C50 C51 H51 119.3 . . ?
C52 C51 C50 121.3(3) . . ?
C52 C51 H51 119.3 . . ?
C51 C52 H52 121.7 . . ?
C51 C52 C53 116.6(3) . . ?
C53 C52 H52 121.7 . . ?
O4 C53 C48 110.7(3) . . ?
O4 C53 C52 125.2(3) . . ?
C52 C53 C48 124.1(3) . . ?
O4 C54 C55 114.2(3) . . ?
C47 C54 O4 111.5(3) . . ?
C47 C54 C55 134.2(3) . . ?
C56 C55 C54 120.5(3) . . ?
C60 C55 C54 119.4(3) . . ?
C60 C55 C56 120.1(3) . . ?
C55 C56 H56 120.7 . . ?
C57 C56 C55 118.6(4) . . ?
C57 C56 H56 120.7 . . ?
C56 C57 H57 119.8 . . ?
C56 C57 C58 120.3(4) . . ?
C58 C57 H57 119.8 . . ?
C57 C58 H58 119.6 . . ?
C59 C58 C57 120.7(4) . . ?
C59 C58 H58 119.6 . . ?
C58 C59 H59 120.3 . . ?
C58 C59 C60 119.3(5) . . ?
C60 C59 H59 120.3 . . ?
C55 C60 C59 120.9(4) . . ?
C55 C60 H60 119.5 . . ?
C59 C60 H60 119.5 . . ?

_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 2.728
_oxdiff_exptl_absorpt_empirical_full_min 0.503
####################################################################### 
# 
# 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_pxc-427
_database_code_depnum_ccdc_archive 'CCDC 2132602'
loop_
_audit_author_name
_audit_author_address
PXC
;Ji Nan University
China
;
_audit_update_record             
;
2022-01-11 deposited with the CCDC.	2022-05-18 downloaded from the CCDC.
;
_audit_creation_date             2022-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C22 H17 N O4)'
_chemical_formula_sum            'C11 H8.50 N0.50 O2'
_chemical_formula_weight         179.68
_chemical_melting_point          ?
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'
H H 0.0000 0.0000 '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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.4698(14)
_cell_length_b                   15.849(4)
_cell_length_c                   13.479(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.852(17)
_cell_angle_gamma                90
_cell_volume                     1782.7(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2932
_cell_measurement_temperature    274(5)
_cell_measurement_theta_max      72.3740
_cell_measurement_theta_min      4.3350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.892
_diffrn_reflns_Laue_measured_fraction_max 0.810
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7329
_diffrn_reflns_point_group_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.202
_diffrn_reflns_theta_min         4.343
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      274(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.892
_diffrn_measured_fraction_theta_max 0.810
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     29.00  88.00   0.50    0.79    --    0.00   0.00 -90.00  118
  2  ω    -69.00   6.00   0.50    0.79    --    0.00 -38.00 120.00  150
  3  ω    -33.00  14.00   0.50    0.79    --    0.00 -38.00 -90.00   94
  4  ω    -85.00 -60.00   0.50    0.79    --    0.00 -38.00 -90.00   50
  5  ω    118.00 155.00   0.50    3.17    --   95.20  15.00-150.00   74
  6  ω    160.00 185.00   0.50    3.17    --   95.20  15.00-150.00   50
  7  ω     13.00 114.00   0.50    3.17    --   95.20 -77.00  30.00  202
  8  ω     76.00 107.00   0.50    3.17    --   95.20 -30.00  30.00   62
  9  ω     79.00 104.00   0.50    3.17    --   95.20  15.00-150.00   50
 10  ω     34.00  67.00   0.50    3.17    --   95.20 -45.00-120.00   66
 11  ω      6.00  38.00   0.50    3.17    --   95.20 -30.00  30.00   64
 12  ω     31.00  98.00   0.50    3.17    --   95.20 -30.00 -90.00  134
 13  ω     80.00 130.00   0.50    3.17    --   95.20  30.00 120.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1721474000
_diffrn_orient_matrix_UB_12      0.0048029000
_diffrn_orient_matrix_UB_13      -0.0217641000
_diffrn_orient_matrix_UB_21      0.0452344000
_diffrn_orient_matrix_UB_22      0.0611781000
_diffrn_orient_matrix_UB_23      0.0891391000
_diffrn_orient_matrix_UB_31      0.0483180000
_diffrn_orient_matrix_UB_32      -0.0754800000
_diffrn_orient_matrix_UB_33      0.0711050000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2242
_reflns_number_total             3099
_reflns_odcompleteness_completeness 89.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3099
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.036
_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)+(0.0755P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1347
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
C1 C 0.2130(2) 0.26981(15) 0.65754(18) 0.0682(7) Uani 1 1 d . . . . .
H1A H 0.2694 0.3083 0.7061 0.102 Uiso 1 1 calc GR . . . .
H1B H 0.1358 0.2389 0.6876 0.102 Uiso 1 1 calc GR . . . .
H1C H 0.1589 0.3008 0.6005 0.102 Uiso 1 1 calc GR . . . .
C2 C 0.3289(2) 0.20999(15) 0.62422(15) 0.0512(5) Uani 1 1 d . . . . .
C3 C 0.4799(2) 0.33081(13) 0.56352(13) 0.0427(4) Uani 1 1 d . . . . .
C4 C 0.4902(2) 0.37166(14) 0.35695(14) 0.0488(5) Uani 1 1 d . . . . .
C5 C 0.4875(3) 0.43001(15) 0.27024(15) 0.0681(6) Uani 1 1 d . . . . .
H5A H 0.4767 0.4870 0.2921 0.102 Uiso 1 1 calc GR . . . .
H5B H 0.3985 0.4162 0.2186 0.102 Uiso 1 1 calc GR . . . .
H5C H 0.5855 0.4244 0.2441 0.102 Uiso 1 1 calc GR . . . .
C6 C 0.63741(19) 0.33810(12) 0.52064(12) 0.0392(4) Uani 1 1 d . . . . .
C7 C 0.76200(19) 0.38281(12) 0.59812(13) 0.0414(4) Uani 1 1 d . . . . .
C8 C 0.8106(3) 0.46443(15) 0.58360(17) 0.0667(6) Uani 1 1 d . . . . .
H8 H 0.7672 0.4938 0.5256 0.080 Uiso 1 1 calc R . . . .
C9 C 0.9251(3) 0.50228(16) 0.6563(2) 0.0823(8) Uani 1 1 d . . . . .
H9 H 0.9591 0.5568 0.6458 0.099 Uiso 1 1 calc R . . . .
C10 C 0.9888(2) 0.46066(16) 0.74340(16) 0.0630(6) Uani 1 1 d . . . . .
H10 H 1.0663 0.4864 0.7910 0.076 Uiso 1 1 calc R . . . .
C11 C 0.9368(2) 0.38066(14) 0.75925(15) 0.0541(5) Uani 1 1 d . . . . .
H11 H 0.9768 0.3525 0.8188 0.065 Uiso 1 1 calc R . . . .
C12 C 0.8256(2) 0.34191(13) 0.68714(13) 0.0475(5) Uani 1 1 d . . . . .
H12 H 0.7924 0.2873 0.6983 0.057 Uiso 1 1 calc R . . . .
C13 C 0.67700(18) 0.24739(12) 0.50410(12) 0.0375(4) Uani 1 1 d . . . . .
C14 C 0.57503(17) 0.19546(13) 0.54359(12) 0.0384(4) Uani 1 1 d . . . . .
C15 C 0.5933(2) 0.10698(13) 0.54335(13) 0.0446(4) Uani 1 1 d . . . . .
H15 H 0.5248 0.0720 0.5716 0.053 Uiso 1 1 calc R . . . .
C16 C 0.7141(2) 0.07441(13) 0.50052(13) 0.0462(4) Uani 1 1 d . . . . .
H16 H 0.7265 0.0161 0.4994 0.055 Uiso 1 1 calc R . . . .
C17 C 0.8216(2) 0.12547(13) 0.45768(13) 0.0427(4) Uani 1 1 d . . . . .
C18 C 0.9459(2) 0.09114(15) 0.41295(15) 0.0574(6) Uani 1 1 d . . . . .
H18 H 0.9566 0.0329 0.4092 0.069 Uiso 1 1 calc R . . . .
C19 C 1.0502(2) 0.14201(17) 0.37528(16) 0.0656(6) Uani 1 1 d . . . . .
H19 H 1.1319 0.1182 0.3464 0.079 Uiso 1 1 calc R . . . .
C20 C 1.0359(2) 0.23036(17) 0.37947(16) 0.0630(6) Uani 1 1 d . . . . .
H20 H 1.1093 0.2644 0.3544 0.076 Uiso 1 1 calc R . . . .
C21 C 0.9152(2) 0.26646(14) 0.42008(15) 0.0523(5) Uani 1 1 d . . . . .
H21 H 0.9053 0.3249 0.4213 0.063 Uiso 1 1 calc R . . . .
C22 C 0.80502(18) 0.21481(13) 0.46046(13) 0.0407(4) Uani 1 1 d . . . . .
N1 N 0.45585(15) 0.24416(10) 0.58208(11) 0.0413(4) Uani 1 1 d . . . . .
O1 O 0.3186(2) 0.13448(11) 0.63275(15) 0.0855(6) Uani 1 1 d . . . . .
O2 O 0.39853(16) 0.38896(9) 0.58088(11) 0.0601(4) Uani 1 1 d . . . . .
O3 O 0.39758(16) 0.31562(10) 0.36409(11) 0.0633(4) Uani 1 1 d . . . . .
O4 O 0.61479(14) 0.38977(8) 0.43132(9) 0.0466(3) 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
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.489(3) . ?
C2 N1 1.407(2) . ?
C2 O1 1.207(2) . ?
C3 C6 1.546(2) . ?
C3 N1 1.417(2) . ?
C3 O2 1.198(2) . ?
C4 C5 1.488(3) . ?
C4 O3 1.200(2) . ?
C4 O4 1.356(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.526(2) . ?
C6 C13 1.502(2) . ?
C6 O4 1.441(2) . ?
C7 C8 1.382(3) . ?
C7 C12 1.389(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.391(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.371(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(2) . ?
C13 C22 1.417(2) . ?
C14 C15 1.411(3) . ?
C14 N1 1.436(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.360(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.413(3) . ?
C17 C18 1.409(2) . ?
C17 C22 1.424(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.357(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.407(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.365(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.418(3) . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 117.8(2) . . ?
O1 C2 C1 122.71(18) . . ?
O1 C2 N1 119.54(18) . . ?
N1 C3 C6 107.32(14) . . ?
O2 C3 C6 125.29(18) . . ?
O2 C3 N1 127.33(17) . . ?
O3 C4 C5 126.92(19) . . ?
O3 C4 O4 122.30(18) . . ?
O4 C4 C5 110.78(18) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C3 108.58(14) . . ?
C13 C6 C3 102.28(13) . . ?
C13 C6 C7 113.60(14) . . ?
O4 C6 C3 110.78(13) . . ?
O4 C6 C7 106.58(15) . . ?
O4 C6 C13 114.90(15) . . ?
C8 C7 C6 121.72(17) . . ?
C8 C7 C12 118.57(18) . . ?
C12 C7 C6 119.68(18) . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.5(2) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.3(2) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(2) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.1(2) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 H12 119.4 . . ?
C11 C12 C7 121.3(2) . . ?
C11 C12 H12 119.4 . . ?
C14 C13 C6 110.31(15) . . ?
C14 C13 C22 121.49(18) . . ?
C22 C13 C6 128.09(16) . . ?
C13 C14 C15 121.42(16) . . ?
C13 C14 N1 110.33(17) . . ?
C15 C14 N1 128.25(15) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 C14 117.98(17) . . ?
C16 C15 H15 121.0 . . ?
C15 C16 H16 118.6 . . ?
C15 C16 C17 122.7(2) . . ?
C17 C16 H16 118.6 . . ?
C16 C17 C22 119.03(16) . . ?
C18 C17 C16 122.3(2) . . ?
C18 C17 C22 118.66(18) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(2) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.67(19) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 119.9(2) . . ?
C22 C21 H21 120.0 . . ?
C13 C22 C17 117.34(16) . . ?
C13 C22 C21 123.35(19) . . ?
C21 C22 C17 119.31(16) . . ?
C2 N1 C3 125.95(16) . . ?
C2 N1 C14 124.86(17) . . ?
C3 N1 C14 109.02(14) . . ?
C4 O4 C6 118.20(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 2.878
_oxdiff_exptl_absorpt_empirical_full_min 0.509
####################################################################### 
# 
# 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_pxc-538
_database_code_depnum_ccdc_archive 'CCDC 2141348'
loop_
_audit_author_name
_audit_author_address
PXC
;Ji Nan University
China
;
_audit_update_record             
;
2022-01-11 deposited with the CCDC.	2022-05-18 downloaded from the CCDC.
;
_audit_creation_date             2022-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.4(C34 H23 N O3)'
_chemical_formula_sum            'C13.60 H9.20 N0.40 O1.20'
_chemical_formula_weight         197.41
_chemical_melting_point          ?
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'
H H 0.0000 0.0000 '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'

_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                   9.5212(4)
_cell_length_b                   10.5180(5)
_cell_length_c                   13.1964(4)
_cell_angle_alpha                101.461(3)
_cell_angle_beta                 95.719(3)
_cell_angle_gamma                98.056(3)
_cell_volume                     1271.29(9)
_cell_formula_units_Z            5
_cell_measurement_reflns_used    8517
_cell_measurement_temperature    295.81(10)
_cell_measurement_theta_max      73.7840
_cell_measurement_theta_min      3.5010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light silver'
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12351
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.626
_diffrn_reflns_theta_min         3.447
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.81(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     47.00  88.00   0.50    0.50    --    0.00  38.00-120.00   82
  2  ω    -13.00  19.00   0.50    0.50    --    0.00 -57.00   0.00   64
  3  ω    -81.00 -55.00   0.50    0.50    --    0.00 -57.00   0.00   52
  4  ω    -50.00  16.00   0.50    0.50    --    0.00 -38.00-120.00  132
  5  ω    -13.00  13.00   0.50    0.50    --    0.00 -19.00 150.00   52
  6  ω    -15.00  27.00   0.50    0.50    --    0.00  38.00-120.00   84
  7  ω    -87.00 -56.00   0.50    0.50    --    0.00 -19.00 150.00   62
  8  ω     74.00 131.00   0.50    0.50    --   95.20  15.00  60.00  114
  9  ω     33.00 103.00   0.50    0.50    --   95.20 -82.00 150.00  140
 10  ω      9.00  55.00   0.50    0.50    --   95.20 -30.00   0.00   92
 11  ω     98.00 124.00   0.50    0.50    --   95.20  30.00 -60.00   52
 12  ω     12.00 118.00   0.50    0.50    --   95.20 -61.00-150.00  212
 13  ω      7.00  69.00   0.50    0.50    --   95.20 -15.00  30.00  124
 14  ω     76.00 119.00   0.50    0.50    --   95.20 -15.00  30.00   86
 15  ω     60.00 120.00   0.50    0.50    --   95.20 -82.00   0.00  120
 16  ω     87.00 181.00   0.50    0.50    --   95.20  30.00 -30.00  188
 17  ω     21.00 127.00   0.50    0.50    --   95.20 -82.00-150.00  212
 18  ω     14.00  39.00   0.50    0.50    --   95.20 -82.00   0.00   50
 19  ω     72.00 114.00   0.50    0.50    --   95.20 -61.00   0.00   84
 20  ω     51.00  95.00   0.50    0.50    --   95.20 -82.00 120.00   88
 21  ω     14.00  67.00   0.50    0.50    --   95.20 -61.00   0.00  106
 22  ω    129.00 175.00   0.50    0.50    --   95.20  30.00 -60.00   92
 23  ω    136.00 182.00   0.50    0.50    --   95.20  15.00  60.00   92
 24  ω     87.00 112.00   0.50    0.50    --   95.20 -30.00   0.00   50
 25  ω      9.00  34.00   0.50    0.50    --   95.20 -82.00  60.00   50
 26  ω     77.00 102.00   0.50    0.50    --   95.20 -82.00  60.00   50
 27  ω     68.00 111.00   0.50    0.50    --   95.20 -82.00 -60.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0649868000
_diffrn_orient_matrix_UB_12      0.1187595000
_diffrn_orient_matrix_UB_13      -0.0418316000
_diffrn_orient_matrix_UB_21      0.0597856000
_diffrn_orient_matrix_UB_22      -0.0930302000
_diffrn_orient_matrix_UB_23      -0.0844785000
_diffrn_orient_matrix_UB_31      -0.1391984000
_diffrn_orient_matrix_UB_32      -0.0139373000
_diffrn_orient_matrix_UB_33      -0.0745080000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4348
_reflns_number_total             4958
_reflns_odcompleteness_completeness 99.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4958
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0622
_refine_ls_restrained_S_all      1.067
_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)+(0.1184P)²+0.2268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1785
_refine_ls_wR_factor_ref         0.1867
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24),
  C27(H27), C28(H28), C29(H29), C30(H30)
2.b Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
C1 C 0.07734(18) 0.30142(17) 0.74809(14) 0.0453(4) Uani 1 1 d . . . . .
C2 C 0.1077(2) 0.17263(17) 0.69857(17) 0.0532(5) Uani 1 1 d . . . . .
C3 C 0.1103(4) 0.0732(2) 0.7533(2) 0.0861(8) Uani 1 1 d . . . . .
H3 H 0.0852 0.0849 0.8205 0.103 Uiso 1 1 calc R . . . .
C4 C 0.1509(5) -0.0442(3) 0.7066(3) 0.1157(12) Uani 1 1 d . . . . .
H4 H 0.1544 -0.1105 0.7436 0.139 Uiso 1 1 calc R . . . .
C5 C 0.1860(4) -0.0639(3) 0.6072(3) 0.1039(11) Uani 1 1 d . . . . .
H5 H 0.2162 -0.1418 0.5780 0.125 Uiso 1 1 calc R . . . .
C6 C 0.1765(3) 0.0308(2) 0.5515(2) 0.0822(8) Uani 1 1 d . . . . .
H6 H 0.1965 0.0165 0.4830 0.099 Uiso 1 1 calc R . . . .
C7 C 0.1371(2) 0.14824(19) 0.59652(18) 0.0596(5) Uani 1 1 d . . . . .
H7 H 0.1302 0.2123 0.5576 0.072 Uiso 1 1 calc R . . . .
C8 C 0.14431(16) 0.42667(15) 0.75774(12) 0.0378(3) Uani 1 1 d . . . . .
C9 C 0.05651(17) 0.51080(17) 0.81381(13) 0.0418(4) Uani 1 1 d . . . . .
C10 C -0.05712(18) 0.42537(19) 0.83544(14) 0.0482(4) Uani 1 1 d . . . . .
C11 C -0.1657(2) 0.4676(2) 0.88901(17) 0.0625(5) Uani 1 1 d . . . . .
H11 H -0.2392 0.4082 0.9032 0.075 Uiso 1 1 calc R . . . .
C12 C -0.1602(2) 0.5999(3) 0.92004(19) 0.0719(6) Uani 1 1 d . . . . .
H12 H -0.2313 0.6318 0.9563 0.086 Uiso 1 1 calc R . . . .
C13 C -0.0499(3) 0.6882(2) 0.8985(2) 0.0686(6) Uani 1 1 d . . . . .
H13 H -0.0496 0.7780 0.9199 0.082 Uiso 1 1 calc R . . . .
C14 C 0.0594(2) 0.64527(19) 0.84564(16) 0.0533(5) Uani 1 1 d . . . . .
H14 H 0.1328 0.7051 0.8319 0.064 Uiso 1 1 calc R . . . .
C15 C 0.28322(16) 0.47290(15) 0.71787(12) 0.0364(3) Uani 1 1 d . . . . .
C16 C 0.39554(18) 0.59163(18) 0.90131(13) 0.0458(4) Uani 1 1 d . . . . .
H16 H 0.3524 0.5197 0.9245 0.055 Uiso 1 1 calc R . . . .
C17 C 0.4798(2) 0.69321(19) 0.97073(14) 0.0519(4) Uani 1 1 d . . . . .
H17 H 0.4917 0.6908 1.0411 0.062 Uiso 1 1 calc R . . . .
C18 C 0.54960(19) 0.80266(18) 0.93748(14) 0.0496(4) Uani 1 1 d . . . . .
C19 C 0.6419(2) 0.9077(2) 1.00731(19) 0.0694(6) Uani 1 1 d . . . . .
H19 H 0.6560 0.9075 1.0780 0.083 Uiso 1 1 calc R . . . .
C20 C 0.7099(3) 1.0086(2) 0.9711(2) 0.0814(8) Uani 1 1 d . . . . .
H20 H 0.7708 1.0770 1.0175 0.098 Uiso 1 1 calc R . . . .
C21 C 0.6898(3) 1.0112(2) 0.8653(2) 0.0828(8) Uani 1 1 d . . . . .
H21 H 0.7379 1.0809 0.8421 0.099 Uiso 1 1 calc R . . . .
C22 C 0.6004(2) 0.9126(2) 0.7957(2) 0.0655(6) Uani 1 1 d . . . . .
H22 H 0.5869 0.9159 0.7255 0.079 Uiso 1 1 calc R . . . .
C23 C 0.52827(18) 0.80520(17) 0.83043(15) 0.0470(4) Uani 1 1 d . . . . .
C24 C 0.43669(17) 0.69942(16) 0.75981(13) 0.0414(4) Uani 1 1 d . . . . .
H24 H 0.4202 0.7019 0.6896 0.050 Uiso 1 1 calc R . . . .
C25 C 0.37266(16) 0.59407(15) 0.79403(12) 0.0380(3) Uani 1 1 d . . . . .
C27 C 0.17518(18) 0.56608(17) 0.56352(14) 0.0446(4) Uani 1 1 d . . . . .
H27 H 0.1236 0.6195 0.6050 0.054 Uiso 1 1 calc R . . . .
C28 C 0.1680(2) 0.5630(2) 0.45743(15) 0.0527(4) Uani 1 1 d . . . . .
H28 H 0.1128 0.6158 0.4278 0.063 Uiso 1 1 calc R . . . .
C29 C 0.2425(2) 0.4820(2) 0.39607(15) 0.0570(5) Uani 1 1 d . . . . .
H29 H 0.2355 0.4797 0.3249 0.068 Uiso 1 1 calc R . . . .
C30 C 0.3278(2) 0.4036(2) 0.43789(14) 0.0519(4) Uani 1 1 d . . . . .
H30 H 0.3778 0.3490 0.3959 0.062 Uiso 1 1 calc R . . . .
C31 C 0.4975(2) 0.24378(19) 0.56729(15) 0.0520(4) Uani 1 1 d . . . . .
C32 C 0.5755(3) 0.1815(3) 0.6416(2) 0.0819(8) Uani 1 1 d . . . . .
H32A H 0.6398 0.2480 0.6921 0.123 Uiso 1 1 calc GR . . . .
H32B H 0.6290 0.1210 0.6044 0.123 Uiso 1 1 calc GR . . . .
H32C H 0.5083 0.1350 0.6766 0.123 Uiso 1 1 calc GR . . . .
C33 C 0.33631(16) 0.40917(15) 0.54387(12) 0.0394(4) Uani 1 1 d . . . . .
C34 C 0.25964(16) 0.48903(15) 0.60664(12) 0.0371(3) Uani 1 1 d . . . . .
C35 C 0.38275(16) 0.36787(15) 0.70957(12) 0.0392(4) Uani 1 1 d . . . . .
N1 N 0.41529(14) 0.33956(13) 0.60668(10) 0.0407(3) Uani 1 1 d . . . . .
O1 O -0.04529(13) 0.29822(13) 0.79698(11) 0.0535(3) Uani 1 1 d . . . . .
O2 O 0.42669(15) 0.32073(14) 0.77965(10) 0.0561(4) Uani 1 1 d . . . . .
O3 O 0.50193(19) 0.21556(17) 0.47436(12) 0.0741(5) 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
C1 C2 1.463(3) . ?
C1 C8 1.356(2) . ?
C1 O1 1.389(2) . ?
C2 C3 1.386(3) . ?
C2 C7 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.358(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.449(2) . ?
C8 C15 1.524(2) . ?
C9 C10 1.397(2) . ?
C9 C14 1.389(2) . ?
C10 C11 1.384(3) . ?
C10 O1 1.358(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.362(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.392(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(3) . ?
C14 H14 0.9300 . ?
C15 C25 1.541(2) . ?
C15 C34 1.509(2) . ?
C15 C35 1.548(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.359(3) . ?
C16 C25 1.417(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.416(3) . ?
C18 C19 1.415(3) . ?
C18 C23 1.413(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.358(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.396(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.365(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.418(3) . ?
C23 C24 1.421(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.367(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.389(2) . ?
C27 C34 1.379(2) . ?
C28 H28 0.9300 . ?
C28 C29 1.377(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.387(3) . ?
C30 H30 0.9300 . ?
C30 C33 1.382(2) . ?
C31 C32 1.480(3) . ?
C31 N1 1.411(2) . ?
C31 O3 1.210(2) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.393(2) . ?
C33 N1 1.435(2) . ?
C35 N1 1.406(2) . ?
C35 O2 1.200(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
C8 C1 C2 133.76(16) . . ?
C8 C1 O1 111.24(15) . . ?
O1 C1 C2 115.01(15) . . ?
C3 C2 C1 120.8(2) . . ?
C7 C2 C1 120.67(17) . . ?
C7 C2 C3 118.5(2) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C2 C7 H7 119.4 . . ?
C6 C7 C2 121.2(2) . . ?
C6 C7 H7 119.4 . . ?
C1 C8 C9 106.24(14) . . ?
C1 C8 C15 127.95(14) . . ?
C9 C8 C15 125.81(13) . . ?
C10 C9 C8 105.33(15) . . ?
C14 C9 C8 136.22(15) . . ?
C14 C9 C10 118.44(15) . . ?
C11 C10 C9 123.44(19) . . ?
O1 C10 C9 110.81(14) . . ?
O1 C10 C11 125.75(17) . . ?
C10 C11 H11 121.5 . . ?
C12 C11 C10 117.09(19) . . ?
C12 C11 H11 121.5 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.17(18) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.5(2) . . ?
C14 C13 H13 119.3 . . ?
C9 C14 H14 120.8 . . ?
C13 C14 C9 118.38(18) . . ?
C13 C14 H14 120.8 . . ?
C8 C15 C25 111.77(12) . . ?
C8 C15 C35 111.72(12) . . ?
C25 C15 C35 104.21(12) . . ?
C34 C15 C8 112.58(12) . . ?
C34 C15 C25 113.98(12) . . ?
C34 C15 C35 101.83(12) . . ?
C17 C16 H16 119.6 . . ?
C17 C16 C25 120.78(16) . . ?
C25 C16 H16 119.6 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 120.96(17) . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 122.26(19) . . ?
C23 C18 C17 118.54(16) . . ?
C23 C18 C19 119.18(19) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.0(2) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.8(2) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.9(2) . . ?
C23 C22 H22 120.1 . . ?
C18 C23 C22 119.13(18) . . ?
C18 C23 C24 119.42(16) . . ?
C22 C23 C24 121.45(18) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.65(16) . . ?
C25 C24 H24 119.7 . . ?
C16 C25 C15 118.58(14) . . ?
C24 C25 C15 121.70(14) . . ?
C24 C25 C16 119.61(15) . . ?
C28 C27 H27 120.4 . . ?
C34 C27 H27 120.4 . . ?
C34 C27 C28 119.24(16) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.10(17) . . ?
C29 C28 H28 119.9 . . ?
C28 C29 H29 119.2 . . ?
C28 C29 C30 121.54(17) . . ?
C30 C29 H29 119.2 . . ?
C29 C30 H30 121.1 . . ?
C33 C30 C29 117.89(17) . . ?
C33 C30 H30 121.1 . . ?
N1 C31 C32 118.58(17) . . ?
O3 C31 C32 122.34(18) . . ?
O3 C31 N1 119.08(18) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 C34 121.21(15) . . ?
C30 C33 N1 129.49(15) . . ?
C34 C33 N1 109.29(13) . . ?
C27 C34 C15 129.47(14) . . ?
C27 C34 C33 120.00(15) . . ?
C33 C34 C15 110.52(13) . . ?
N1 C35 C15 108.37(13) . . ?
O2 C35 C15 125.67(14) . . ?
O2 C35 N1 125.95(15) . . ?
C31 N1 C33 124.47(14) . . ?
C35 N1 C31 125.21(14) . . ?
C35 N1 C33 109.80(12) . . ?
C10 O1 C1 106.34(13) . . ?

_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 3.057
_oxdiff_exptl_absorpt_empirical_full_min 0.413
