# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_1_0m
_audit_block_doi                 10.5517/ccdc.csd.cc294sdn
_database_code_depnum_ccdc_archive 'CCDC 2119761'
loop_
_audit_author_name
_audit_author_address
'jingwei Huang'
;CCZU
China
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-03-08 downloaded from the CCDC.
;
_audit_creation_date             2021-10-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H35 N O'
_chemical_formula_sum            'C31 H35 N O'
_chemical_formula_weight         437.60
_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 0.0033 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/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                   12.0537(10)
_cell_length_b                   13.4766(11)
_cell_length_c                   30.162(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.446(3)
_cell_angle_gamma                90
_cell_volume                     4890.8(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4552
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.369
_cell_measurement_theta_min      2.268
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1262 before and 0.0704 after correction. The Ratio of minimum to maximum transmission is 0.7782. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1053
_diffrn_reflns_av_unetI/netI     0.1044
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            40415
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.420
_diffrn_reflns_theta_min         2.028
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4835
_reflns_number_total             9922
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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         0.318
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         9922
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1862
_refine_ls_R_factor_gt           0.0897
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0678P)²+8.2314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1991
_refine_ls_wR_factor_ref         0.2438
_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:
 C27(H27), C59(H59), C47(H47), C17(H17), C24(H24), C15(H15), C25(H25),
 C42(H42), C46(H46), C10(H10), C6(H6), C57(H57), C49(H49), C7(H7), C44(H44),
 C37(H37)
2.b Idealised Me refined as rotating group:
 C62(H62A,H62B,H62C), C61(H61A,H61B,H61C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C63(H63A,H63B,H63C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C4(H4A,
 H4B,H4C), C19(H19A,H19B,H19C), C1(H1A,H1B,H1C), C29(H29A,H29B,H29C), C3(H3A,
 H3B,H3C), C34(H34A,H34B,H34C), C32(H32A,H32B,H32C), C55(H55A,H55B,H55C),
 C35(H35A,H35B,H35C), C54(H54A,H54B,H54C), C53(H53A,H53B,H53C)
;
_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 0.2356(2) 0.8001(2) 0.65880(10) 0.0478(8) Uani 1 1 d . . . . .
N2 N 0.0208(3) 1.0089(2) 0.73752(11) 0.0347(8) Uani 1 1 d . . . . .
O2 O -0.2248(3) 0.9509(2) 0.82387(10) 0.0525(8) Uani 1 1 d . . . . .
N1 N -0.0054(3) 0.7278(2) 0.74495(10) 0.0338(8) Uani 1 1 d . . . . .
C45 C 0.0825(3) 1.0203(3) 0.69965(13) 0.0343(9) Uani 1 1 d . . . . .
C41 C -0.0835(3) 0.9734(3) 0.72303(13) 0.0355(10) Uani 1 1 d . . . . .
C14 C 0.1058(3) 0.7730(3) 0.80592(13) 0.0346(9) Uani 1 1 d . . . . .
C23 C -0.0682(3) 0.7158(3) 0.78301(13) 0.0336(9) Uani 1 1 d . . . . .
C13 C 0.0987(3) 0.7634(3) 0.75957(13) 0.0349(9) Uani 1 1 d . . . . .
C22 C -0.0010(3) 0.7433(3) 0.82082(13) 0.0344(9) Uani 1 1 d . . . . .
C12 C 0.1844(3) 0.7880(3) 0.73318(13) 0.0359(10) Uani 1 1 d . . . . .
C56 C -0.0904(3) 0.9621(3) 0.67692(13) 0.0369(10) Uani 1 1 d . . . . .
C43 C 0.0432(3) 1.0249(3) 0.78280(13) 0.0343(9) Uani 1 1 d . . . . .
C38 C -0.0394(3) 1.0012(3) 0.81251(13) 0.0340(9) Uani 1 1 d . . . . .
C26 C -0.1516(4) 0.7114(3) 0.86819(13) 0.0382(10) Uani 1 1 d . . . . .
C27 C -0.0433(3) 0.7416(3) 0.86222(14) 0.0381(10) Uani 1 1 d . . . . .
H27 H 0.002739 0.761472 0.887318 0.046 Uiso 1 1 calc R . . . .
C59 C -0.2686(3) 0.9182(3) 0.72817(14) 0.0392(10) Uani 1 1 d . . . . .
H59 H -0.329483 0.903164 0.745579 0.047 Uiso 1 1 calc R . . . .
C47 C 0.2292(4) 1.0568(3) 0.65252(13) 0.0387(10) Uani 1 1 d . . . . .
H47 H 0.303252 1.078503 0.649302 0.046 Uiso 1 1 calc R . . . .
C17 C 0.2831(3) 0.8196(3) 0.75506(14) 0.0377(10) Uani 1 1 d . . . . .
H17 H 0.343795 0.836582 0.737844 0.045 Uiso 1 1 calc R . . . .
C9 C 0.0546(3) 0.7375(3) 0.66992(14) 0.0370(10) Uani 1 1 d . . . . .
C50 C 0.0163(3) 0.9929(3) 0.66178(14) 0.0384(10) Uani 1 1 d . . . . .
C40 C -0.1689(3) 0.9512(3) 0.74943(13) 0.0372(10) Uani 1 1 d . . . . .
C8 C -0.0270(3) 0.7111(3) 0.69940(13) 0.0357(10) Uani 1 1 d . . . . .
C5 C -0.0637(4) 0.6806(3) 0.60670(13) 0.0408(10) Uani 1 1 d . . . . .
C11 C 0.1653(3) 0.7786(3) 0.68463(14) 0.0387(10) Uani 1 1 d . . . . .
C16 C 0.2967(3) 0.8273(3) 0.80087(15) 0.0405(10) Uani 1 1 d . . . . .
C24 C -0.1766(3) 0.6857(3) 0.78770(13) 0.0367(10) Uani 1 1 d . . . . .
H24 H -0.223127 0.666968 0.762548 0.044 Uiso 1 1 calc R . . . .
C39 C -0.1516(3) 0.9657(3) 0.79746(14) 0.0378(10) Uani 1 1 d . . . . .
C15 C 0.2057(3) 0.8045(3) 0.82620(13) 0.0380(10) Uani 1 1 d . . . . .
H15 H 0.212941 0.810953 0.857607 0.046 Uiso 1 1 calc R . . . .
C25 C -0.2159(4) 0.6836(3) 0.83011(14) 0.0406(10) Uani 1 1 d . . . . .
H25 H -0.290032 0.662227 0.833360 0.049 Uiso 1 1 calc R . . . .
C42 C 0.1437(3) 1.0633(3) 0.80020(14) 0.0401(10) Uani 1 1 d . . . . .
H42 H 0.199715 1.080941 0.780787 0.048 Uiso 1 1 calc R . . . .
C46 C 0.1914(3) 1.0527(3) 0.69441(13) 0.0382(10) Uani 1 1 d . . . . .
H46 H 0.238196 1.071472 0.719467 0.046 Uiso 1 1 calc R . . . .
C10 C 0.0328(4) 0.7228(3) 0.62428(14) 0.0407(10) Uani 1 1 d . . . . .
H10 H 0.087176 0.742860 0.604606 0.049 Uiso 1 1 calc R . . . .
C36 C 0.0841(4) 1.0499(3) 0.87580(14) 0.0402(10) Uani 1 1 d . . . . .
C6 C -0.1418(4) 0.6509(3) 0.63694(14) 0.0430(11) Uani 1 1 d . . . . .
H6 H -0.208524 0.619561 0.625982 0.052 Uiso 1 1 calc R . . . .
C57 C -0.1907(3) 0.9273(3) 0.65703(14) 0.0394(10) Uani 1 1 d . . . . .
H57 H -0.197297 0.917572 0.625788 0.047 Uiso 1 1 calc R . . . .
C48 C 0.1640(4) 1.0304(3) 0.61387(14) 0.0408(10) Uani 1 1 d . . . . .
C49 C 0.0576(3) 0.9981(3) 0.61985(13) 0.0377(10) Uani 1 1 d . . . . .
H49 H 0.011361 0.978851 0.594699 0.045 Uiso 1 1 calc R . . . .
C7 C -0.1241(4) 0.6662(3) 0.68215(14) 0.0420(11) Uani 1 1 d . . . . .
H7 H -0.178893 0.645780 0.701618 0.050 Uiso 1 1 calc R . . . .
C58 C -0.2811(3) 0.9068(3) 0.68217(14) 0.0398(10) Uani 1 1 d . . . . .
C60 C -0.3945(4) 0.8744(3) 0.66114(15) 0.0466(11) Uani 1 1 d . . . . .
C44 C 0.1627(4) 1.0758(3) 0.84508(14) 0.0419(11) Uani 1 1 d . . . . .
H44 H 0.231822 1.102993 0.855946 0.050 Uiso 1 1 calc R . . . .
C18 C 0.4097(4) 0.8576(3) 0.82293(15) 0.0449(11) Uani 1 1 d . . . . .
C37 C -0.0162(4) 1.0147(3) 0.85771(13) 0.0403(10) Uani 1 1 d . . . . .
H37 H -0.072551 0.998985 0.877285 0.048 Uiso 1 1 calc R . . . .
C2 C -0.0886(4) 0.6616(4) 0.55688(14) 0.0501(12) Uani 1 1 d . . . . .
C28 C -0.1995(4) 0.7164(3) 0.91402(14) 0.0445(11) Uani 1 1 d . . . . .
C51 C 0.2140(4) 1.0341(3) 0.56900(14) 0.0454(11) Uani 1 1 d . . . . .
C33 C 0.1081(4) 1.0621(4) 0.92554(14) 0.0495(12) Uani 1 1 d . . . . .
C62 C -0.4840(4) 0.9478(4) 0.67457(16) 0.0538(12) Uani 1 1 d . . . . .
H62A H -0.482949 0.951995 0.707027 0.081 Uiso 1 1 calc GR . . . .
H62B H -0.557187 0.924804 0.662929 0.081 Uiso 1 1 calc GR . . . .
H62C H -0.468969 1.013464 0.662310 0.081 Uiso 1 1 calc GR . . . .
C61 C -0.4218(4) 0.7699(4) 0.67740(18) 0.0626(14) Uani 1 1 d . . . . .
H61A H -0.369022 0.722242 0.666069 0.094 Uiso 1 1 calc GR . . . .
H61B H -0.497475 0.751979 0.666582 0.094 Uiso 1 1 calc GR . . . .
H61C H -0.416478 0.768662 0.709947 0.094 Uiso 1 1 calc GR . . . .
C20 C 0.4991(4) 0.7853(4) 0.80858(18) 0.0619(14) Uani 1 1 d . . . . .
H20A H 0.486413 0.719678 0.821329 0.093 Uiso 1 1 calc GR . . . .
H20B H 0.572661 0.809576 0.819155 0.093 Uiso 1 1 calc GR . . . .
H20C H 0.495416 0.780474 0.776110 0.093 Uiso 1 1 calc GR . . . .
C21 C 0.4405(4) 0.9622(4) 0.80772(18) 0.0641(14) Uani 1 1 d . . . . .
H21A H 0.437326 0.964519 0.775192 0.096 Uiso 1 1 calc GR . . . .
H21B H 0.515856 0.978461 0.819446 0.096 Uiso 1 1 calc GR . . . .
H21C H 0.387879 1.010350 0.818801 0.096 Uiso 1 1 calc GR . . . .
C63 C -0.3962(4) 0.8732(4) 0.61052(15) 0.0637(15) Uani 1 1 d . . . . .
H63A H -0.376457 0.939081 0.599741 0.095 Uiso 1 1 calc GR . . . .
H63B H -0.470828 0.855425 0.598392 0.095 Uiso 1 1 calc GR . . . .
H63C H -0.342486 0.824274 0.600913 0.095 Uiso 1 1 calc GR . . . .
C30 C -0.2281(5) 0.8246(4) 0.92343(16) 0.0670(15) Uani 1 1 d . . . . .
H30A H -0.159607 0.863936 0.926195 0.101 Uiso 1 1 calc GR . . . .
H30B H -0.266206 0.828650 0.951172 0.101 Uiso 1 1 calc GR . . . .
H30C H -0.276751 0.850719 0.898956 0.101 Uiso 1 1 calc GR . . . .
C31 C -0.3067(5) 0.6569(4) 0.91638(17) 0.0734(17) Uani 1 1 d . . . . .
H31A H -0.360730 0.679032 0.892856 0.110 Uiso 1 1 calc GR . . . .
H31B H -0.337442 0.667195 0.945385 0.110 Uiso 1 1 calc GR . . . .
H31C H -0.290889 0.586236 0.912418 0.110 Uiso 1 1 calc GR . . . .
C4 C -0.1997(4) 0.7077(4) 0.54148(16) 0.0671(15) Uani 1 1 d . . . . .
H4A H -0.259496 0.675581 0.556817 0.101 Uiso 1 1 calc GR . . . .
H4B H -0.212602 0.698458 0.509357 0.101 Uiso 1 1 calc GR . . . .
H4C H -0.198588 0.778790 0.548366 0.101 Uiso 1 1 calc GR . . . .
C19 C 0.4110(4) 0.8568(5) 0.87311(17) 0.0766(18) Uani 1 1 d . . . . .
H19A H 0.358927 0.906818 0.883059 0.115 Uiso 1 1 calc GR . . . .
H19B H 0.486089 0.872031 0.885480 0.115 Uiso 1 1 calc GR . . . .
H19C H 0.388757 0.791099 0.883291 0.115 Uiso 1 1 calc GR . . . .
C1 C -0.0002(4) 0.7075(5) 0.52864(15) 0.0691(16) Uani 1 1 d . . . . .
H1A H 0.005359 0.778836 0.534736 0.104 Uiso 1 1 calc GR . . . .
H1B H -0.021199 0.697106 0.497093 0.104 Uiso 1 1 calc GR . . . .
H1C H 0.071808 0.675969 0.536062 0.104 Uiso 1 1 calc GR . . . .
C29 C -0.1162(5) 0.6789(5) 0.94995(16) 0.0777(18) Uani 1 1 d . . . . .
H29A H -0.098322 0.609302 0.944097 0.117 Uiso 1 1 calc GR . . . .
H29B H -0.148158 0.684189 0.978960 0.117 Uiso 1 1 calc GR . . . .
H29C H -0.048243 0.718820 0.949942 0.117 Uiso 1 1 calc GR . . . .
C3 C -0.0923(6) 0.5496(4) 0.54873(17) 0.0834(19) Uani 1 1 d . . . . .
H3A H -0.020179 0.520370 0.558122 0.125 Uiso 1 1 calc GR . . . .
H3B H -0.108548 0.536706 0.517023 0.125 Uiso 1 1 calc GR . . . .
H3C H -0.150390 0.519833 0.565814 0.125 Uiso 1 1 calc GR . . . .
C34 C 0.0076(5) 1.1039(5) 0.94690(18) 0.091(2) Uani 1 1 d . . . . .
H34A H -0.011171 1.168802 0.933878 0.137 Uiso 1 1 calc GR . . . .
H34B H 0.024511 1.111281 0.978916 0.137 Uiso 1 1 calc GR . . . .
H34C H -0.055422 1.058605 0.941720 0.137 Uiso 1 1 calc GR . . . .
C32 C 0.1302(6) 0.9590(5) 0.94553(19) 0.108(3) Uani 1 1 d . . . . .
H32A H 0.065813 0.916179 0.938562 0.162 Uiso 1 1 calc GR . . . .
H32B H 0.142844 0.964731 0.977833 0.162 Uiso 1 1 calc GR . . . .
H32C H 0.196080 0.930210 0.933001 0.162 Uiso 1 1 calc GR . . . .
C55 C 0.1272(5) 1.0312(7) 0.53093(17) 0.109(3) Uani 1 1 d . . . . .
H55A H 0.084805 0.969334 0.532163 0.163 Uiso 1 1 calc GR . . . .
H55B H 0.163631 1.034502 0.502775 0.163 Uiso 1 1 calc GR . . . .
H55C H 0.076877 1.087846 0.533086 0.163 Uiso 1 1 calc GR . . . .
C35 C 0.2046(7) 1.1277(8) 0.9359(2) 0.158(5) Uani 1 1 d . . . . .
H35A H 0.271194 1.098369 0.924195 0.237 Uiso 1 1 calc GR . . . .
H35B H 0.215847 1.135293 0.968203 0.237 Uiso 1 1 calc GR . . . .
H35C H 0.190605 1.192839 0.922291 0.237 Uiso 1 1 calc GR . . . .
C54 C 0.2819(6) 1.1283(6) 0.5631(2) 0.119(3) Uani 1 1 d . . . . .
H54A H 0.232561 1.186102 0.562735 0.178 Uiso 1 1 calc GR . . . .
H54B H 0.318455 1.124726 0.534981 0.178 Uiso 1 1 calc GR . . . .
H54C H 0.338201 1.134374 0.587748 0.178 Uiso 1 1 calc GR . . . .
C53 C 0.2914(9) 0.9489(7) 0.5653(2) 0.182(5) Uani 1 1 d . . . . .
H53A H 0.351452 0.953829 0.588577 0.274 Uiso 1 1 calc GR . . . .
H53B H 0.322908 0.950105 0.536097 0.274 Uiso 1 1 calc GR . . . .
H53C H 0.250818 0.886636 0.568774 0.274 Uiso 1 1 calc GR . . . .


_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 C11 1.220(5) . ?
N2 C45 1.408(5) . ?
N2 C41 1.391(5) . ?
N2 C43 1.393(5) . ?
O2 C39 1.240(5) . ?
N1 C23 1.422(5) . ?
N1 C13 1.390(5) . ?
N1 C8 1.401(5) . ?
C45 C50 1.403(5) . ?
C45 C46 1.401(6) . ?
C41 C56 1.397(6) . ?
C41 C40 1.372(6) . ?
C14 C13 1.401(5) . ?
C14 C22 1.445(6) . ?
C14 C15 1.385(5) . ?
C23 C22 1.408(5) . ?
C23 C24 1.384(5) . ?
C13 C12 1.382(5) . ?
C22 C27 1.377(5) . ?
C12 C17 1.392(5) . ?
C12 C11 1.474(6) . ?
C56 C50 1.451(6) . ?
C56 C57 1.397(6) . ?
C43 C38 1.415(5) . ?
C43 C42 1.391(6) . ?
C38 C39 1.480(6) . ?
C38 C37 1.387(5) . ?
C26 C27 1.389(6) . ?
C26 C25 1.397(6) . ?
C26 C28 1.531(6) . ?
C27 H27 0.9500 . ?
C59 H59 0.9500 . ?
C59 C40 1.399(6) . ?
C59 C58 1.395(6) . ?
C47 H47 0.9500 . ?
C47 C46 1.370(5) . ?
C47 C48 1.412(6) . ?
C17 H17 0.9500 . ?
C17 C16 1.386(6) . ?
C9 C8 1.411(6) . ?
C9 C11 1.488(6) . ?
C9 C10 1.400(6) . ?
C50 C49 1.389(6) . ?
C40 C39 1.464(6) . ?
C8 C7 1.391(6) . ?
C5 C10 1.372(6) . ?
C5 C6 1.408(6) . ?
C5 C2 1.536(6) . ?
C16 C15 1.407(6) . ?
C16 C18 1.535(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.391(5) . ?
C15 H15 0.9500 . ?
C25 H25 0.9500 . ?
C42 H42 0.9500 . ?
C42 C44 1.370(6) . ?
C46 H46 0.9500 . ?
C10 H10 0.9500 . ?
C36 C44 1.409(6) . ?
C36 C37 1.380(6) . ?
C36 C33 1.520(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(6) . ?
C57 H57 0.9500 . ?
C57 C58 1.392(6) . ?
C48 C49 1.376(6) . ?
C48 C51 1.515(6) . ?
C49 H49 0.9500 . ?
C7 H7 0.9500 . ?
C58 C60 1.535(6) . ?
C60 C62 1.536(6) . ?
C60 C61 1.534(6) . ?
C60 C63 1.526(6) . ?
C44 H44 0.9500 . ?
C18 C20 1.535(6) . ?
C18 C21 1.535(6) . ?
C18 C19 1.513(6) . ?
C37 H37 0.9500 . ?
C2 C4 1.524(7) . ?
C2 C1 1.535(7) . ?
C2 C3 1.530(7) . ?
C28 C30 1.529(6) . ?
C28 C31 1.526(7) . ?
C28 C29 1.520(6) . ?
C51 C55 1.506(6) . ?
C51 C54 1.526(8) . ?
C51 C53 1.489(8) . ?
C33 C34 1.514(7) . ?
C33 C32 1.531(8) . ?
C33 C35 1.479(7) . ?
C62 H62A 0.9800 . ?
C62 H62B 0.9800 . ?
C62 H62C 0.9800 . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C63 H63A 0.9800 . ?
C63 H63B 0.9800 . ?
C63 H63C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?

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
C41 N2 C45 107.1(3) . . ?
C41 N2 C43 118.6(3) . . ?
C43 N2 C45 134.3(3) . . ?
C13 N1 C23 107.3(3) . . ?
C13 N1 C8 118.6(3) . . ?
C8 N1 C23 134.1(3) . . ?
C50 C45 N2 109.2(3) . . ?
C46 C45 N2 132.0(4) . . ?
C46 C45 C50 118.8(4) . . ?
N2 C41 C56 110.4(4) . . ?
C40 C41 N2 126.0(4) . . ?
C40 C41 C56 123.5(4) . . ?
C13 C14 C22 106.4(4) . . ?
C15 C14 C13 117.9(4) . . ?
C15 C14 C22 135.6(4) . . ?
C22 C23 N1 108.4(3) . . ?
C24 C23 N1 131.9(4) . . ?
C24 C23 C22 119.7(4) . . ?
N1 C13 C14 110.4(3) . . ?
C12 C13 N1 126.3(4) . . ?
C12 C13 C14 123.3(4) . . ?
C23 C22 C14 107.5(3) . . ?
C27 C22 C14 132.2(4) . . ?
C27 C22 C23 120.3(4) . . ?
C13 C12 C17 116.6(4) . . ?
C13 C12 C11 118.3(4) . . ?
C17 C12 C11 125.1(4) . . ?
C41 C56 C50 106.3(4) . . ?
C41 C56 C57 117.6(4) . . ?
C57 C56 C50 136.1(4) . . ?
N2 C43 C38 118.9(4) . . ?
C42 C43 N2 122.7(4) . . ?
C42 C43 C38 118.3(4) . . ?
C43 C38 C39 122.9(4) . . ?
C37 C38 C43 119.0(4) . . ?
C37 C38 C39 118.0(4) . . ?
C27 C26 C25 116.8(4) . . ?
C27 C26 C28 120.8(4) . . ?
C25 C26 C28 122.2(4) . . ?
C22 C27 C26 121.6(4) . . ?
C22 C27 H27 119.2 . . ?
C26 C27 H27 119.2 . . ?
C40 C59 H59 119.0 . . ?
C58 C59 H59 119.0 . . ?
C58 C59 C40 121.9(4) . . ?
C46 C47 H47 118.2 . . ?
C46 C47 C48 123.5(4) . . ?
C48 C47 H47 118.2 . . ?
C12 C17 H17 118.6 . . ?
C16 C17 C12 122.8(4) . . ?
C16 C17 H17 118.6 . . ?
C8 C9 C11 123.6(4) . . ?
C10 C9 C8 119.1(4) . . ?
C10 C9 C11 117.3(4) . . ?
C45 C50 C56 106.9(4) . . ?
C49 C50 C45 120.7(4) . . ?
C49 C50 C56 132.4(4) . . ?
C41 C40 C59 117.2(4) . . ?
C41 C40 C39 118.5(4) . . ?
C59 C40 C39 124.3(4) . . ?
N1 C8 C9 118.8(4) . . ?
C7 C8 N1 122.7(4) . . ?
C7 C8 C9 118.5(4) . . ?
C10 C5 C6 116.8(4) . . ?
C10 C5 C2 124.0(4) . . ?
C6 C5 C2 119.2(4) . . ?
O1 C11 C12 122.8(4) . . ?
O1 C11 C9 122.9(4) . . ?
C12 C11 C9 114.3(4) . . ?
C17 C16 C15 118.4(4) . . ?
C17 C16 C18 120.0(4) . . ?
C15 C16 C18 121.5(4) . . ?
C23 C24 H24 120.8 . . ?
C23 C24 C25 118.4(4) . . ?
C25 C24 H24 120.8 . . ?
O2 C39 C38 121.9(4) . . ?
O2 C39 C40 123.3(4) . . ?
C40 C39 C38 114.8(4) . . ?
C14 C15 C16 120.8(4) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C26 C25 H25 118.4 . . ?
C24 C25 C26 123.2(4) . . ?
C24 C25 H25 118.4 . . ?
C43 C42 H42 119.7 . . ?
C44 C42 C43 120.6(4) . . ?
C44 C42 H42 119.7 . . ?
C45 C46 H46 120.6 . . ?
C47 C46 C45 118.8(4) . . ?
C47 C46 H46 120.6 . . ?
C9 C10 H10 118.5 . . ?
C5 C10 C9 122.9(4) . . ?
C5 C10 H10 118.5 . . ?
C44 C36 C33 121.8(4) . . ?
C37 C36 C44 115.7(4) . . ?
C37 C36 C33 122.6(4) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.8(4) . . ?
C7 C6 H6 119.1 . . ?
C56 C57 H57 119.4 . . ?
C58 C57 C56 121.2(4) . . ?
C58 C57 H57 119.4 . . ?
C47 C48 C51 119.9(4) . . ?
C49 C48 C47 116.6(4) . . ?
C49 C48 C51 123.4(4) . . ?
C50 C49 H49 119.2 . . ?
C48 C49 C50 121.6(4) . . ?
C48 C49 H49 119.2 . . ?
C8 C7 H7 119.7 . . ?
C6 C7 C8 120.7(4) . . ?
C6 C7 H7 119.7 . . ?
C59 C58 C60 118.9(4) . . ?
C57 C58 C59 118.6(4) . . ?
C57 C58 C60 122.5(4) . . ?
C58 C60 C62 109.2(4) . . ?
C61 C60 C58 109.4(4) . . ?
C61 C60 C62 109.8(4) . . ?
C63 C60 C58 112.0(4) . . ?
C63 C60 C62 107.6(4) . . ?
C63 C60 C61 108.7(4) . . ?
C42 C44 C36 122.7(4) . . ?
C42 C44 H44 118.7 . . ?
C36 C44 H44 118.7 . . ?
C20 C18 C16 109.2(4) . . ?
C21 C18 C16 109.8(4) . . ?
C21 C18 C20 108.2(4) . . ?
C19 C18 C16 112.8(4) . . ?
C19 C18 C20 108.2(4) . . ?
C19 C18 C21 108.5(4) . . ?
C38 C37 H37 118.2 . . ?
C36 C37 C38 123.6(4) . . ?
C36 C37 H37 118.2 . . ?
C4 C2 C5 110.3(4) . . ?
C4 C2 C1 107.1(4) . . ?
C4 C2 C3 109.7(5) . . ?
C1 C2 C5 112.0(4) . . ?
C3 C2 C5 108.9(4) . . ?
C3 C2 C1 108.9(4) . . ?
C30 C28 C26 108.1(4) . . ?
C31 C28 C26 112.7(4) . . ?
C31 C28 C30 107.0(4) . . ?
C29 C28 C26 111.1(4) . . ?
C29 C28 C30 109.4(4) . . ?
C29 C28 C31 108.5(4) . . ?
C48 C51 C54 112.1(4) . . ?
C55 C51 C48 112.7(4) . . ?
C55 C51 C54 106.6(5) . . ?
C53 C51 C48 109.1(4) . . ?
C53 C51 C55 109.4(6) . . ?
C53 C51 C54 106.8(6) . . ?
C36 C33 C32 108.0(4) . . ?
C34 C33 C36 110.5(4) . . ?
C34 C33 C32 107.1(5) . . ?
C35 C33 C36 112.0(4) . . ?
C35 C33 C34 109.0(5) . . ?
C35 C33 C32 110.0(6) . . ?
C60 C62 H62A 109.5 . . ?
C60 C62 H62B 109.5 . . ?
C60 C62 H62C 109.5 . . ?
H62A C62 H62B 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C60 C61 H61A 109.5 . . ?
C60 C61 H61B 109.5 . . ?
C60 C61 H61C 109.5 . . ?
H61A C61 H61B 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C60 C63 H63A 109.5 . . ?
C60 C63 H63B 109.5 . . ?
C60 C63 H63C 109.5 . . ?
H63A C63 H63B 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C32 H32A 109.5 . . ?
C33 C32 H32B 109.5 . . ?
C33 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C51 C55 H55A 109.5 . . ?
C51 C55 H55B 109.5 . . ?
C51 C55 H55C 109.5 . . ?
H55A C55 H55B 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C51 C54 H54A 109.5 . . ?
C51 C54 H54B 109.5 . . ?
C51 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C51 C53 H53A 109.5 . . ?
C51 C53 H53B 109.5 . . ?
C51 C53 H53C 109.5 . . ?
H53A C53 H53B 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc294sgq
_database_code_depnum_ccdc_archive 'CCDC 2119763'
loop_
_audit_author_name
_audit_author_address
'jingwei Huang'
;CCZU
China
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-03-08 downloaded from the CCDC.
;
_audit_creation_date             2021-01-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18.98 H11 N O1.84'
_chemical_formula_sum            'C19 H11 N O2'
_chemical_formula_weight         285.29
_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 0.0033 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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   16.5609(16)
_cell_length_b                   7.5103(9)
_cell_length_c                   20.848(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2593.0(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3223
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.50
_cell_measurement_theta_min      3.13
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7563
_exptl_absorpt_correction_T_min  0.5642
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 22680 reflections, Rint = 0.0819
 (8713 with I > 3sig(I), Rint = 0.0557)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4904
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.450
_diffrn_reflns_theta_min         2.460
_diffrn_ambient_temperature      185.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1643
_reflns_number_total             2658
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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         0.860
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2658
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0729
_refine_ls_restrained_S_all      1.042
_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)+(0.0985P)²+1.3360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1791
_refine_ls_wR_factor_ref         0.2100
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(O19)=Sof(C20)=FVAR(1)
 Fixed Sof: O2(0.85524)
3.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C10(H10), C8(H8), C17(H17), C3(H3), C4(H4), C15(H15), C2(H2),
 C9(H9), C16(H16), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O19 O 0.45724(13) 0.1419(3) 0.24599(12) 0.0542(9) Uani 0.984(7) 1 d . . P A 1
N1 N 0.32987(13) 0.3115(3) 0.30804(12) 0.0408(6) Uani 1 1 d . . . . .
O2 O 0.35390(17) 0.4883(4) 0.49089(13) 0.0593(8) Uani 0.8552 1 d . . P A 1
C12 C 0.33203(17) 0.3083(4) 0.24029(15) 0.0394(7) Uani 1 1 d . . . . .
C20 C 0.34561(19) 0.4232(4) 0.43810(15) 0.0428(9) Uani 0.984(7) 1 d . . P A 1
C11 C 0.27612(17) 0.3959(4) 0.20112(15) 0.0442(8) Uani 1 1 d . . . . .
H11 H 0.234423 0.464779 0.220183 0.053 Uiso 1 1 calc R . . . .
C6 C 0.40373(16) 0.2928(4) 0.33998(15) 0.0396(7) Uani 1 1 d . . . . .
C13 C 0.25972(18) 0.3390(4) 0.34492(15) 0.0422(7) Uani 1 1 d . . . . .
C14 C 0.26700(18) 0.3978(4) 0.40816(15) 0.0444(8) Uani 1 1 d . . . . .
C7 C 0.39602(17) 0.2206(4) 0.21016(16) 0.0432(7) Uani 1 1 d . . . . .
C1 C 0.41357(18) 0.3471(4) 0.40326(15) 0.0442(8) Uani 1 1 d . . . . .
C5 C 0.46802(18) 0.2106(4) 0.30767(16) 0.0460(8) Uani 1 1 d . . . . .
C10 C 0.28070(19) 0.3836(4) 0.13518(16) 0.0506(8) Uani 1 1 d . . . . .
H10 H 0.241788 0.442344 0.109224 0.061 Uiso 1 1 calc R . . . .
C8 C 0.39975(19) 0.2064(4) 0.14426(16) 0.0490(8) Uani 1 1 d . . . . .
H8 H 0.442411 0.141522 0.124739 0.059 Uiso 1 1 calc R . . . .
C17 C 0.18282(17) 0.3004(4) 0.32027(18) 0.0485(8) Uani 1 1 d . . . . .
H17 H 0.177506 0.255156 0.277935 0.058 Uiso 1 1 calc R . . . .
C3 C 0.5513(2) 0.2416(5) 0.4004(2) 0.0600(10) Uani 1 1 d . . . . .
H3 H 0.601887 0.224971 0.421040 0.072 Uiso 1 1 calc R . . . .
C4 C 0.54086(19) 0.1864(4) 0.33780(19) 0.0562(9) Uani 1 1 d . . . . .
H4 H 0.584242 0.131424 0.315507 0.067 Uiso 1 1 calc R . . . .
C15 C 0.1971(2) 0.4244(4) 0.44499(17) 0.0550(9) Uani 1 1 d . . . . .
H15 H 0.201596 0.465625 0.487912 0.066 Uiso 1 1 calc R . . . .
C2 C 0.4889(2) 0.3202(4) 0.43287(18) 0.0562(9) Uani 1 1 d . . . . .
H2 H 0.496662 0.357256 0.476011 0.067 Uiso 1 1 calc R . . . .
C9 C 0.3418(2) 0.2861(5) 0.10684(17) 0.0541(9) Uani 1 1 d . . . . .
H9 H 0.343742 0.274166 0.061500 0.065 Uiso 1 1 calc R . . . .
C16 C 0.1151(2) 0.3279(4) 0.3572(2) 0.0591(10) Uani 1 1 d . . . . .
H16 H 0.063149 0.303438 0.339937 0.071 Uiso 1 1 calc R . . . .
C18 C 0.1220(2) 0.3908(5) 0.4191(2) 0.0635(11) Uani 1 1 d . . . . .
H18 H 0.074819 0.411095 0.444062 0.076 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
O19 C7 1.391(4) . ?
O19 C5 1.397(4) . ?
N1 C12 1.413(4) . ?
N1 C6 1.400(4) . ?
N1 C13 1.408(4) . ?
O2 C20 1.212(4) . ?
C12 C11 1.399(4) . ?
C12 C7 1.397(4) . ?
C20 C14 1.456(4) . ?
C20 C1 1.457(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.380(4) . ?
C6 C1 1.390(4) . ?
C6 C5 1.403(4) . ?
C13 C14 1.396(4) . ?
C13 C17 1.403(4) . ?
C14 C15 1.403(4) . ?
C7 C8 1.379(4) . ?
C1 C2 1.407(4) . ?
C5 C4 1.372(4) . ?
C10 H10 0.9500 . ?
C10 C9 1.382(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.374(5) . ?
C17 H17 0.9500 . ?
C17 C16 1.377(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(5) . ?
C3 C2 1.368(5) . ?
C4 H4 0.9500 . ?
C15 H15 0.9500 . ?
C15 C18 1.380(5) . ?
C2 H2 0.9500 . ?
C9 H9 0.9500 . ?
C16 H16 0.9500 . ?
C16 C18 1.379(5) . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O19 C5 115.5(2) . . ?
C6 N1 C12 116.9(2) . . ?
C6 N1 C13 118.4(3) . . ?
C13 N1 C12 124.7(2) . . ?
C11 C12 N1 124.0(3) . . ?
C7 C12 N1 118.5(3) . . ?
C7 C12 C11 117.5(3) . . ?
O2 C20 C14 122.9(3) . . ?
O2 C20 C1 121.6(3) . . ?
C14 C20 C1 115.2(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.5 . . ?
N1 C6 C5 118.6(3) . . ?
C1 C6 N1 121.6(3) . . ?
C1 C6 C5 119.7(3) . . ?
C14 C13 N1 119.4(3) . . ?
C14 C13 C17 119.3(3) . . ?
C17 C13 N1 121.2(3) . . ?
C13 C14 C20 121.6(3) . . ?
C13 C14 C15 119.4(3) . . ?
C15 C14 C20 118.9(3) . . ?
C12 C7 O19 120.8(3) . . ?
C8 C7 O19 118.0(3) . . ?
C8 C7 C12 121.2(3) . . ?
C6 C1 C20 119.9(3) . . ?
C6 C1 C2 118.6(3) . . ?
C2 C1 C20 121.5(3) . . ?
O19 C5 C6 120.5(3) . . ?
C4 C5 O19 119.0(3) . . ?
C4 C5 C6 120.4(3) . . ?
C11 C10 H10 119.9 . . ?
C11 C10 C9 120.1(3) . . ?
C9 C10 H10 119.9 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 120.0 . . ?
C13 C17 H17 119.9 . . ?
C16 C17 C13 120.3(3) . . ?
C16 C17 H17 119.9 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(3) . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C14 C15 H15 119.9 . . ?
C18 C15 C14 120.3(3) . . ?
C18 C15 H15 119.9 . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.5 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 C10 120.0(3) . . ?
C8 C9 H9 120.0 . . ?
C17 C16 H16 119.8 . . ?
C17 C16 C18 120.5(3) . . ?
C18 C16 H16 119.8 . . ?
C15 C18 C16 120.2(3) . . ?
C15 C18 H18 119.9 . . ?
C16 C18 H18 119.9 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3_0m
_audit_block_doi                 10.5517/ccdc.csd.cc294sfp
_database_code_depnum_ccdc_archive 'CCDC 2119762'
loop_
_audit_author_name
_audit_author_address
'jingwei Huang'
;CCZU
China
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-03-08 downloaded from the CCDC.
;
_audit_creation_date             2021-01-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 N O'
_chemical_formula_sum            'C22 H17 N O'
_chemical_formula_weight         311.36
_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 0.0033 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                   8.6697(7)
_cell_length_b                   9.9227(8)
_cell_length_c                   10.4685(8)
_cell_angle_alpha                70.490(3)
_cell_angle_beta                 67.026(3)
_cell_angle_gamma                75.263(3)
_cell_volume                     773.51(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3392
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.395
_cell_measurement_theta_min      2.664
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0984 before and 0.0498 after correction. The Ratio of minimum to maximum transmission is 0.8642. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8675
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.433
_diffrn_reflns_theta_min         2.191
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2337
_reflns_number_total             3145
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.019
_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)+(0.0549P)²+0.2795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1281
_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:
 C1(H1), C4(H4), C14(H14), C19(H19), C2(H2), C22(H22), C20(H20), C13(H13),
 C3(H3), C12(H12), C21(H21)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_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 0.52826(17) 0.83067(15) 0.24596(13) 0.0386(3) Uani 1 1 d . . . . .
N1 N 0.41382(17) 0.71538(15) 0.68351(14) 0.0247(3) Uani 1 1 d . . . . .
C6 C 0.3257(2) 0.74341(18) 0.82206(17) 0.0249(4) Uani 1 1 d . . . . .
C5 C 0.4193(2) 0.77075(18) 0.89095(17) 0.0251(4) Uani 1 1 d . . . . .
C15 C 0.5948(2) 0.82966(18) 0.44475(18) 0.0259(4) Uani 1 1 d . . . . .
C1 C 0.1496(2) 0.75727(19) 0.88013(18) 0.0286(4) Uani 1 1 d . . . . .
H1 H 0.086994 0.741271 0.830908 0.034 Uiso 1 1 calc R . . . .
C11 C 0.5529(2) 0.78904(18) 0.59478(17) 0.0239(4) Uani 1 1 d . . . . .
C18 C 0.3421(2) 0.65086(18) 0.62337(18) 0.0256(4) Uani 1 1 d . . . . .
C16 C 0.5012(2) 0.78862(18) 0.37694(18) 0.0280(4) Uani 1 1 d . . . . .
C4 C 0.3318(2) 0.8092(2) 1.01989(19) 0.0312(4) Uani 1 1 d . . . . .
H4 H 0.393132 0.828567 1.068158 0.037 Uiso 1 1 calc R . . . .
C17 C 0.3798(2) 0.68820(18) 0.47384(18) 0.0268(4) Uani 1 1 d . . . . .
C7 C 0.6107(2) 0.75802(19) 0.82155(18) 0.0275(4) Uani 1 1 d . . . . .
C14 C 0.7314(2) 0.90623(19) 0.35921(18) 0.0291(4) Uani 1 1 d . . . . .
H14 H 0.760637 0.934241 0.257514 0.035 Uiso 1 1 calc R . . . .
C10 C 0.6494(2) 0.82035(18) 0.66013(18) 0.0251(4) Uani 1 1 d . . . . .
C19 C 0.2392(2) 0.5431(2) 0.71022(19) 0.0298(4) Uani 1 1 d . . . . .
H19 H 0.216800 0.513528 0.811177 0.036 Uiso 1 1 calc R . . . .
C2 C 0.0658(2) 0.7941(2) 1.00886(19) 0.0340(4) Uani 1 1 d . . . . .
H2 H -0.054078 0.801952 1.048946 0.041 Uiso 1 1 calc R . . . .
C22 C 0.3079(2) 0.6218(2) 0.41545(19) 0.0312(4) Uani 1 1 d . . . . .
H22 H 0.332161 0.647970 0.314330 0.037 Uiso 1 1 calc R . . . .
C20 C 0.1706(2) 0.4801(2) 0.6499(2) 0.0331(4) Uani 1 1 d . . . . .
H20 H 0.099838 0.408230 0.710063 0.040 Uiso 1 1 calc R . . . .
C13 C 0.8232(2) 0.9409(2) 0.4219(2) 0.0341(4) Uani 1 1 d . . . . .
H13 H 0.914588 0.994562 0.363864 0.041 Uiso 1 1 calc R . . . .
C3 C 0.1571(2) 0.8196(2) 1.0792(2) 0.0356(4) Uani 1 1 d . . . . .
H3 H 0.100044 0.844330 1.168115 0.043 Uiso 1 1 calc R . . . .
C12 C 0.7821(2) 0.8973(2) 0.57095(19) 0.0325(4) Uani 1 1 d . . . . .
H12 H 0.847534 0.921375 0.612729 0.039 Uiso 1 1 calc R . . . .
C21 C 0.2032(2) 0.5200(2) 0.5018(2) 0.0344(4) Uani 1 1 d . . . . .
H21 H 0.153530 0.477064 0.461376 0.041 Uiso 1 1 calc R . . . .
C8 C 0.6862(2) 0.5968(2) 0.8501(2) 0.0366(5) Uani 1 1 d . . . . .
H8A H 0.660805 0.554314 0.953838 0.055 Uiso 1 1 calc GR . . . .
H8B H 0.809123 0.587298 0.801862 0.055 Uiso 1 1 calc GR . . . .
H8C H 0.636612 0.546300 0.812734 0.055 Uiso 1 1 calc GR . . . .
C9 C 0.6881(2) 0.8343(2) 0.8829(2) 0.0371(5) Uani 1 1 d . . . . .
H9A H 0.644098 0.937650 0.862689 0.056 Uiso 1 1 calc GR . . . .
H9B H 0.811505 0.821233 0.838142 0.056 Uiso 1 1 calc GR . . . .
H9C H 0.657961 0.792819 0.987153 0.056 Uiso 1 1 calc GR . . . .


_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 C16 1.235(2) . ?
N1 C6 1.436(2) . ?
N1 C11 1.404(2) . ?
N1 C18 1.404(2) . ?
C6 C5 1.397(2) . ?
C6 C1 1.394(2) . ?
C5 C4 1.393(2) . ?
C5 C7 1.520(2) . ?
C15 C11 1.403(2) . ?
C15 C16 1.463(2) . ?
C15 C14 1.399(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(2) . ?
C11 C10 1.409(2) . ?
C18 C17 1.403(2) . ?
C18 C19 1.403(2) . ?
C16 C17 1.468(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.385(3) . ?
C17 C22 1.404(2) . ?
C7 C10 1.522(2) . ?
C7 C8 1.542(3) . ?
C7 C9 1.535(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.371(2) . ?
C10 C12 1.382(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.374(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(2) . ?
C22 H22 0.9500 . ?
C22 C21 1.370(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.394(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.394(2) . ?
C3 H3 0.9500 . ?
C12 H12 0.9500 . ?
C21 H21 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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
C11 N1 C6 116.33(13) . . ?
C18 N1 C6 122.03(13) . . ?
C18 N1 C11 119.51(13) . . ?
C5 C6 N1 118.26(14) . . ?
C1 C6 N1 120.93(14) . . ?
C1 C6 C5 120.51(15) . . ?
C6 C5 C7 118.62(14) . . ?
C4 C5 C6 118.08(15) . . ?
C4 C5 C7 123.30(15) . . ?
C11 C15 C16 120.77(15) . . ?
C14 C15 C11 119.38(15) . . ?
C14 C15 C16 119.82(15) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 C6 120.33(16) . . ?
C2 C1 H1 119.8 . . ?
N1 C11 C10 118.38(14) . . ?
C15 C11 N1 120.63(14) . . ?
C15 C11 C10 120.99(15) . . ?
C17 C18 N1 120.16(15) . . ?
C19 C18 N1 120.87(15) . . ?
C19 C18 C17 118.88(15) . . ?
O1 C16 C15 122.06(16) . . ?
O1 C16 C17 122.39(16) . . ?
C15 C16 C17 115.47(14) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.36(16) . . ?
C3 C4 H4 119.3 . . ?
C18 C17 C16 121.10(15) . . ?
C18 C17 C22 119.40(16) . . ?
C22 C17 C16 119.38(15) . . ?
C5 C7 C10 107.31(13) . . ?
C5 C7 C8 108.88(15) . . ?
C5 C7 C9 111.73(14) . . ?
C10 C7 C8 108.29(14) . . ?
C10 C7 C9 112.00(15) . . ?
C9 C7 C8 108.54(14) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 C15 120.12(16) . . ?
C13 C14 H14 119.9 . . ?
C11 C10 C7 118.44(15) . . ?
C12 C10 C11 117.33(15) . . ?
C12 C10 C7 124.05(15) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.31(17) . . ?
C20 C19 H19 119.8 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.73(17) . . ?
C3 C2 H2 120.1 . . ?
C17 C22 H22 119.4 . . ?
C21 C22 C17 121.12(16) . . ?
C21 C22 H22 119.4 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.06(17) . . ?
C21 C20 H20 119.5 . . ?
C14 C13 H13 120.1 . . ?
C14 C13 C12 119.81(16) . . ?
C12 C13 H13 120.1 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 119.97(16) . . ?
C2 C3 H3 120.0 . . ?
C10 C12 C13 122.32(16) . . ?
C10 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C22 C21 C20 119.16(16) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_zz
_audit_block_doi                 10.5517/ccdc.csd.cc294shr
_database_code_depnum_ccdc_archive 'CCDC 2119764'
loop_
_audit_author_name
_audit_author_address
'jingwei Huang'
;CCZU
China
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-03-08 downloaded from the CCDC.
;
_audit_creation_date             2019-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H11 N O S'
_chemical_formula_sum            'C19 H11 N O S'
_chemical_formula_weight         301.35
_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 0.0033 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'
S S 0.1246 0.1234 '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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   16.3178(4)
_cell_length_b                   8.1324(2)
_cell_length_c                   20.2196(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2683.20(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6542
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.270
_cell_measurement_theta_min      2.370
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.7582
_exptl_absorpt_correction_T_min  0.5412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker;sadabs;2016
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23433
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.379
_diffrn_reflns_theta_min         2.370
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2185
_reflns_number_total             2733
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.547
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2733
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.009
_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)+(0.0650P)²+3.5385P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1369
_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:
 C5(H5), C8(H8), C2(H2), C11(H11), C19(H19), C9(H9), C17(H17), C4(H4), C3(H3),
 C10(H10), C18(H18)
;
_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
S1 S 0.54532(4) 0.95645(8) 0.23645(3) 0.0311(2) Uani 1 1 d . . . . .
O1 O 0.63771(12) 0.5216(2) 0.48613(9) 0.0378(5) Uani 1 1 d . . . . .
N1 N 0.67011(11) 0.7539(3) 0.30913(9) 0.0245(4) Uani 1 1 d . . . . .
C6 C 0.67199(14) 0.7339(3) 0.23873(11) 0.0230(5) Uani 1 1 d . . . . .
C15 C 0.59278(13) 0.7592(3) 0.34049(11) 0.0243(5) Uani 1 1 d . . . . .
C5 C 0.72697(13) 0.6287(3) 0.20802(11) 0.0238(5) Uani 1 1 d . . . . .
H5 H 0.763891 0.565483 0.233974 0.029 Uiso 1 1 calc R . . . .
C13 C 0.64769(15) 0.5990(3) 0.43735(11) 0.0293(6) Uani 1 1 d . . . . .
C8 C 0.81777(14) 0.7556(3) 0.32622(12) 0.0273(5) Uani 1 1 d . . . . .
H8 H 0.824500 0.812485 0.285550 0.033 Uiso 1 1 calc R . . . .
C2 C 0.61566(15) 0.8021(3) 0.13137(12) 0.0288(5) Uani 1 1 d . . . . .
H2 H 0.576360 0.859120 0.105353 0.035 Uiso 1 1 calc R . . . .
C12 C 0.72993(14) 0.6359(3) 0.40932(11) 0.0258(5) Uani 1 1 d . . . . .
C14 C 0.57990(15) 0.6841(3) 0.40198(12) 0.0262(5) Uani 1 1 d . . . . .
C7 C 0.73930(14) 0.7129(3) 0.34791(11) 0.0246(5) Uani 1 1 d . . . . .
C1 C 0.61521(14) 0.8189(3) 0.19958(12) 0.0254(5) Uani 1 1 d . . . . .
C11 C 0.79998(16) 0.5963(3) 0.44645(12) 0.0306(6) Uani 1 1 d . . . . .
H11 H 0.793956 0.543048 0.487981 0.037 Uiso 1 1 calc R . . . .
C16 C 0.52820(14) 0.8446(3) 0.31016(12) 0.0268(5) Uani 1 1 d . . . . .
C19 C 0.50216(16) 0.6936(3) 0.43136(13) 0.0333(6) Uani 1 1 d . . . . .
H19 H 0.493052 0.641880 0.472852 0.040 Uiso 1 1 calc R . . . .
C9 C 0.88534(15) 0.7153(3) 0.36361(12) 0.0315(6) Uani 1 1 d . . . . .
H9 H 0.938484 0.743829 0.348237 0.038 Uiso 1 1 calc R . . . .
C17 C 0.45221(15) 0.8522(3) 0.34031(13) 0.0320(6) Uani 1 1 d . . . . .
H17 H 0.408623 0.909558 0.319395 0.038 Uiso 1 1 calc R . . . .
C4 C 0.72841(14) 0.6150(3) 0.13940(12) 0.0277(5) Uani 1 1 d . . . . .
H4 H 0.767436 0.545196 0.118723 0.033 Uiso 1 1 calc R . . . .
C3 C 0.67322(15) 0.7026(3) 0.10117(12) 0.0299(6) Uani 1 1 d . . . . .
H3 H 0.674922 0.694429 0.054318 0.036 Uiso 1 1 calc R . . . .
C10 C 0.87682(16) 0.6334(3) 0.42364(13) 0.0338(6) Uani 1 1 d . . . . .
H10 H 0.923863 0.603441 0.448564 0.041 Uiso 1 1 calc R . . . .
C18 C 0.43917(16) 0.7760(4) 0.40129(14) 0.0366(6) Uani 1 1 d . . . . .
H18 H 0.386866 0.781268 0.421812 0.044 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
S1 C1 1.763(2) . ?
S1 C16 1.768(3) . ?
O1 C13 1.181(3) . ?
N1 C6 1.433(3) . ?
N1 C15 1.413(3) . ?
N1 C7 1.414(3) . ?
C6 C5 1.387(3) . ?
C6 C1 1.401(3) . ?
C15 C14 1.401(3) . ?
C15 C16 1.403(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.392(3) . ?
C13 C12 1.487(3) . ?
C13 C14 1.488(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.397(3) . ?
C8 C9 1.376(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.386(3) . ?
C2 C3 1.382(4) . ?
C12 C7 1.399(3) . ?
C12 C11 1.405(3) . ?
C14 C19 1.403(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.370(4) . ?
C16 C17 1.383(3) . ?
C19 H19 0.9500 . ?
C19 C18 1.369(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.396(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.385(3) . ?
C3 H3 0.9500 . ?
C10 H10 0.9500 . ?
C18 H18 0.9500 . ?

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
C1 S1 C16 97.60(11) . . ?
C15 N1 C6 117.92(18) . . ?
C15 N1 C7 118.12(19) . . ?
C7 N1 C6 120.45(19) . . ?
C5 C6 N1 121.9(2) . . ?
C5 C6 C1 118.6(2) . . ?
C1 C6 N1 119.4(2) . . ?
C14 C15 N1 121.3(2) . . ?
C14 C15 C16 119.4(2) . . ?
C16 C15 N1 119.3(2) . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
O1 C13 C12 123.4(2) . . ?
O1 C13 C14 123.1(2) . . ?
C12 C13 C14 113.2(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C9 C8 C7 120.2(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C3 C2 C1 120.0(2) . . ?
C7 C12 C13 121.8(2) . . ?
C7 C12 C11 119.2(2) . . ?
C11 C12 C13 119.0(2) . . ?
C15 C14 C13 121.2(2) . . ?
C15 C14 C19 119.2(2) . . ?
C19 C14 C13 119.6(2) . . ?
C8 C7 N1 119.9(2) . . ?
C8 C7 C12 119.3(2) . . ?
C12 C7 N1 120.7(2) . . ?
C6 C1 S1 120.12(18) . . ?
C2 C1 S1 119.11(18) . . ?
C2 C1 C6 120.7(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 C12 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
C15 C16 S1 120.28(18) . . ?
C17 C16 S1 119.36(19) . . ?
C17 C16 C15 120.2(2) . . ?
C14 C19 H19 119.4 . . ?
C18 C19 C14 121.2(2) . . ?
C18 C19 H19 119.4 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.9(2) . . ?
C10 C9 H9 119.6 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.9 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C19 C18 C17 119.7(2) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
