# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_f-1
_database_code_depnum_ccdc_archive 'CCDC 2175261'
loop_
_audit_author_name
_audit_author_address
'Fu '
;Nanjing Forestry University
China
;
_audit_update_record             
;
2022-05-27 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;
_audit_creation_date             2020-07-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 Cl2 N O S'
_chemical_formula_sum            'C15 H9 Cl2 N O S'
_chemical_formula_weight         322.19
_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'
Cl Cl 0.1484 0.1585 '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      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                   16.3755(11)
_cell_length_b                   7.2951(4)
_cell_length_c                   23.9248(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.152(7)
_cell_angle_gamma                90
_cell_volume                     2783.1(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4353
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      29.3660
_cell_measurement_theta_min      2.9150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11896
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.555
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00   8.00   1.00    2.50    --   11.90 -99.00   0.00   26
  2  ω    -15.00  85.00   1.00    2.50    --   11.90  57.00-150.00  100
  3  ω    -32.00  40.00   1.00    2.50    --   11.90 -19.00  30.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0205936000
_diffrn_orient_matrix_UB_12      0.0028809000
_diffrn_orient_matrix_UB_13      0.0294615000
_diffrn_orient_matrix_UB_21      0.0351915000
_diffrn_orient_matrix_UB_22      0.0426744000
_diffrn_orient_matrix_UB_23      -0.0072626000
_diffrn_orient_matrix_UB_31      -0.0178977000
_diffrn_orient_matrix_UB_32      0.0871547000
_diffrn_orient_matrix_UB_33      0.0025046000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3941
_reflns_number_total             4906
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4906
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0494P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1170
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C19(H19),
 C20(H20), C21(H21), C22(H22), C27(H27), C28(H28), C29(H29)
;
_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 0.34149(17) 0.1987(4) 0.27978(11) 0.0176(6) Uani 1 1 d . . . . .
C2 C 0.40384(18) 0.2121(4) 0.24916(11) 0.0225(7) Uani 1 1 d . . . . .
H2 H 0.459625 0.221990 0.268782 0.027 Uiso 1 1 calc R U . . .
C3 C 0.38385(18) 0.2109(4) 0.18975(12) 0.0238(7) Uani 1 1 d . . . . .
H3 H 0.425786 0.217923 0.169354 0.029 Uiso 1 1 calc R U . . .
C4 C 0.30120(18) 0.1991(4) 0.16145(11) 0.0224(7) Uani 1 1 d . . . . .
H4 H 0.287309 0.198088 0.121533 0.027 Uiso 1 1 calc R U . . .
C5 C 0.23792(18) 0.1887(3) 0.19129(11) 0.0181(6) Uani 1 1 d . . . . .
H5 H 0.182269 0.182084 0.171163 0.022 Uiso 1 1 calc R U . . .
C6 C 0.25684(17) 0.1882(3) 0.25090(10) 0.0152(6) Uani 1 1 d . . . . .
C7 C 0.18793(17) 0.1817(4) 0.28399(11) 0.0204(6) Uani 1 1 d . . . . .
H7A H 0.190446 0.064648 0.303517 0.024 Uiso 1 1 calc R U . . .
H7B H 0.198196 0.276971 0.313042 0.024 Uiso 1 1 calc R U . . .
C8 C 0.1040(2) 0.2061(4) 0.24792(12) 0.0233(7) Uani 1 1 d . . . . .
C9 C 0.36501(17) 0.1895(4) 0.34413(11) 0.0196(6) Uani 1 1 d . . . . .
C10 C 0.46245(18) 0.2985(4) 0.44772(11) 0.0209(6) Uani 1 1 d . . . . .
C11 C 0.54000(18) 0.2269(4) 0.47604(12) 0.0223(6) Uani 1 1 d . . . . .
C12 C 0.55840(19) 0.1889(4) 0.53392(12) 0.0260(7) Uani 1 1 d . . . . .
H12 H 0.610493 0.141633 0.551926 0.031 Uiso 1 1 calc R U . . .
C13 C 0.4986(2) 0.2219(4) 0.56461(12) 0.0289(7) Uani 1 1 d . . . . .
H13 H 0.510554 0.196021 0.603687 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4211(2) 0.2929(4) 0.53863(12) 0.0259(7) Uani 1 1 d . . . . .
H14 H 0.381067 0.314324 0.559885 0.031 Uiso 1 1 calc R U . . .
C15 C 0.40397(18) 0.3315(4) 0.48082(12) 0.0232(7) Uani 1 1 d . . . . .
Cl1 Cl 0.30739(5) 0.42598(10) 0.44966(3) 0.0304(2) Uani 1 1 d . . . . .
Cl2 Cl 0.61664(5) 0.18614(11) 0.43808(3) 0.0330(2) Uani 1 1 d . . . . .
N1 N 0.03849(18) 0.2241(4) 0.21932(11) 0.0384(7) Uani 1 1 d . . . . .
O1 O 0.33352(12) 0.0859(3) 0.37234(8) 0.0259(5) Uani 1 1 d . . . . .
S1 S 0.44372(5) 0.35395(10) 0.37405(3) 0.0240(2) Uani 1 1 d . . . . .
C16 C 0.7152(2) 0.4906(5) 0.36151(13) 0.0323(8) Uani 1 1 d . . . . .
C17 C 0.67478(18) 0.4658(4) 0.30106(11) 0.0253(7) Uani 1 1 d . . . . .
H17A H 0.634345 0.563286 0.289004 0.030 Uiso 1 1 calc R U . . .
H17B H 0.644638 0.350282 0.296288 0.030 Uiso 1 1 calc R U . . .
C18 C 0.73777(17) 0.4666(4) 0.26300(11) 0.0191(6) Uani 1 1 d . . . . .
C19 C 0.82275(18) 0.4652(4) 0.28642(12) 0.0231(6) Uani 1 1 d . . . . .
H19 H 0.841688 0.468459 0.326126 0.028 Uiso 1 1 calc R U . . .
C20 C 0.88069(19) 0.4592(4) 0.25245(12) 0.0282(7) Uani 1 1 d . . . . .
H20 H 0.937737 0.455847 0.269363 0.034 Uiso 1 1 calc R U . . .
C21 C 0.85381(19) 0.4583(4) 0.19356(13) 0.0301(7) Uani 1 1 d . . . . .
H21 H 0.892426 0.453775 0.170478 0.036 Uiso 1 1 calc R U . . .
C22 C 0.76924(18) 0.4642(4) 0.16926(12) 0.0259(7) Uani 1 1 d . . . . .
H22 H 0.751254 0.466233 0.129489 0.031 Uiso 1 1 calc R U . . .
C23 C 0.70983(17) 0.4672(4) 0.20269(11) 0.0194(6) Uani 1 1 d . . . . .
C24 C 0.61943(18) 0.4599(4) 0.17499(11) 0.0206(6) Uani 1 1 d . . . . .
C25 C 0.49268(17) 0.4961(4) 0.08012(10) 0.0194(6) Uani 1 1 d . . . . .
C26 C 0.41929(18) 0.5963(4) 0.07689(11) 0.0226(7) Uani 1 1 d . . . . .
C27 C 0.34157(19) 0.5273(4) 0.05026(12) 0.0275(7) Uani 1 1 d . . . . .
H27 H 0.293318 0.596266 0.048579 0.033 Uiso 1 1 calc R U . . .
C28 C 0.3366(2) 0.3546(4) 0.02619(12) 0.0286(7) Uani 1 1 d . . . . .
H28 H 0.284597 0.308142 0.007564 0.034 Uiso 1 1 calc R U . . .
C29 C 0.40762(19) 0.2501(4) 0.02942(11) 0.0254(7) Uani 1 1 d . . . . .
H29 H 0.403736 0.132703 0.013878 0.030 Uiso 1 1 calc R U . . .
C30 C 0.48456(18) 0.3220(4) 0.05603(11) 0.0218(7) Uani 1 1 d . . . . .
Cl3 Cl 0.42393(5) 0.81449(10) 0.10653(3) 0.0353(2) Uani 1 1 d . . . . .
Cl4 Cl 0.57309(5) 0.18848(11) 0.05930(3) 0.0326(2) Uani 1 1 d . . . . .
N2 N 0.74733(18) 0.5103(5) 0.40862(12) 0.0518(9) Uani 1 1 d . . . . .
O2 O 0.56782(12) 0.3763(3) 0.19335(8) 0.0282(5) Uani 1 1 d . . . . .
S2 S 0.59233(5) 0.59095(10) 0.10998(3) 0.0254(2) 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 1.389(4) . ?
C1 C6 1.403(4) . ?
C1 C9 1.501(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(3) . ?
C6 C7 1.519(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.459(4) . ?
C8 N1 1.141(3) . ?
C9 O1 1.205(3) . ?
C9 S1 1.787(3) . ?
C10 C11 1.397(4) . ?
C10 C15 1.395(4) . ?
C10 S1 1.766(3) . ?
C11 C12 1.377(4) . ?
C11 Cl2 1.734(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(4) . ?
C15 Cl1 1.731(3) . ?
C16 C17 1.458(4) . ?
C16 N2 1.139(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.523(4) . ?
C18 C19 1.377(4) . ?
C18 C23 1.411(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.377(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.375(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.393(4) . ?
C23 C24 1.479(4) . ?
C24 O2 1.203(3) . ?
C24 S2 1.793(3) . ?
C25 C26 1.394(4) . ?
C25 C30 1.389(4) . ?
C25 S2 1.767(3) . ?
C26 C27 1.382(4) . ?
C26 Cl3 1.737(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.380(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.379(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.379(4) . ?
C30 Cl4 1.733(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
C2 C1 C6 120.4(2) . . ?
C2 C1 C9 119.8(2) . . ?
C6 C1 C9 119.8(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 118.9(2) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 120.8(2) . . ?
C5 C6 C1 118.0(2) . . ?
C5 C6 C7 121.1(2) . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 C6 113.6(2) . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
N1 C8 C7 179.3(3) . . ?
C1 C9 S1 111.99(19) . . ?
O1 C9 C1 124.0(2) . . ?
O1 C9 S1 124.0(2) . . ?
C11 C10 C15 117.0(2) . . ?
C11 C10 S1 120.1(2) . . ?
C15 C10 S1 122.8(2) . . ?
C10 C11 Cl2 119.8(2) . . ?
C12 C11 C10 122.0(3) . . ?
C12 C11 Cl2 118.3(2) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 118.9(3) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.3(3) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
C10 C15 Cl1 120.1(2) . . ?
C14 C15 C10 121.7(3) . . ?
C14 C15 Cl1 118.1(2) . . ?
C10 S1 C9 101.05(13) . . ?
N2 C16 C17 179.5(3) . . ?
C16 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C16 C17 C18 112.1(2) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C19 C18 C17 121.0(2) . . ?
C19 C18 C23 118.6(2) . . ?
C23 C18 C17 120.3(2) . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.7(3) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.3(3) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 119.2 . . ?
C21 C22 C23 121.7(3) . . ?
C23 C22 H22 119.2 . . ?
C18 C23 C24 121.1(2) . . ?
C22 C23 C18 118.7(3) . . ?
C22 C23 C24 120.1(2) . . ?
C23 C24 S2 113.23(19) . . ?
O2 C24 C23 124.7(2) . . ?
O2 C24 S2 122.1(2) . . ?
C26 C25 S2 121.5(2) . . ?
C30 C25 C26 117.2(3) . . ?
C30 C25 S2 121.2(2) . . ?
C25 C26 Cl3 120.1(2) . . ?
C27 C26 C25 121.8(3) . . ?
C27 C26 Cl3 118.2(2) . . ?
C26 C27 H27 120.5 . . ?
C28 C27 C26 119.1(3) . . ?
C28 C27 H27 120.5 . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.8(3) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 120.5 . . ?
C28 C29 C30 119.1(3) . . ?
C30 C29 H29 120.5 . . ?
C25 C30 Cl4 119.7(2) . . ?
C29 C30 C25 122.0(3) . . ?
C29 C30 Cl4 118.3(2) . . ?
C25 S2 C24 99.53(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 1.0(4) . . . . ?
C1 C6 C7 C8 169.0(2) . . . . ?
C1 C9 S1 C10 -176.02(19) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
C2 C1 C6 C7 -177.3(2) . . . . ?
C2 C1 C9 O1 -136.5(3) . . . . ?
C2 C1 C9 S1 44.8(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C4 C5 C6 C7 178.4(2) . . . . ?
C5 C6 C7 C8 -9.3(4) . . . . ?
C6 C1 C2 C3 -1.6(4) . . . . ?
C6 C1 C9 O1 41.7(4) . . . . ?
C6 C1 C9 S1 -137.1(2) . . . . ?
C9 C1 C2 C3 176.5(3) . . . . ?
C9 C1 C6 C5 -177.1(2) . . . . ?
C9 C1 C6 C7 4.5(4) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C11 C10 C15 C14 -1.0(4) . . . . ?
C11 C10 C15 Cl1 178.2(2) . . . . ?
C11 C10 S1 C9 113.6(2) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C10 0.8(4) . . . . ?
C13 C14 C15 Cl1 -178.3(2) . . . . ?
C15 C10 C11 C12 0.4(4) . . . . ?
C15 C10 C11 Cl2 -178.8(2) . . . . ?
C15 C10 S1 C9 -69.7(2) . . . . ?
Cl2 C11 C12 C13 179.5(2) . . . . ?
O1 C9 S1 C10 5.2(3) . . . . ?
S1 C10 C11 C12 177.3(2) . . . . ?
S1 C10 C11 Cl2 -2.0(3) . . . . ?
S1 C10 C15 C14 -177.7(2) . . . . ?
S1 C10 C15 Cl1 1.4(3) . . . . ?
C16 C17 C18 C19 8.4(4) . . . . ?
C16 C17 C18 C23 -172.1(3) . . . . ?
C17 C18 C19 C20 177.6(3) . . . . ?
C17 C18 C23 C22 -178.7(3) . . . . ?
C17 C18 C23 C24 -2.4(4) . . . . ?
C18 C19 C20 C21 1.4(4) . . . . ?
C18 C23 C24 O2 -34.9(4) . . . . ?
C18 C23 C24 S2 144.9(2) . . . . ?
C19 C18 C23 C22 0.8(4) . . . . ?
C19 C18 C23 C24 177.1(2) . . . . ?
C19 C20 C21 C22 0.3(5) . . . . ?
C20 C21 C22 C23 -1.4(5) . . . . ?
C21 C22 C23 C18 0.8(4) . . . . ?
C21 C22 C23 C24 -175.6(3) . . . . ?
C22 C23 C24 O2 141.4(3) . . . . ?
C22 C23 C24 S2 -38.8(3) . . . . ?
C23 C18 C19 C20 -1.9(4) . . . . ?
C23 C24 S2 C25 163.36(19) . . . . ?
C25 C26 C27 C28 0.0(4) . . . . ?
C26 C25 C30 C29 0.6(4) . . . . ?
C26 C25 C30 Cl4 -179.17(19) . . . . ?
C26 C25 S2 C24 109.5(2) . . . . ?
C26 C27 C28 C29 1.2(4) . . . . ?
C27 C28 C29 C30 -1.4(4) . . . . ?
C28 C29 C30 C25 0.5(4) . . . . ?
C28 C29 C30 Cl4 -179.7(2) . . . . ?
C30 C25 C26 C27 -0.8(4) . . . . ?
C30 C25 C26 Cl3 179.44(19) . . . . ?
C30 C25 S2 C24 -74.0(2) . . . . ?
Cl3 C26 C27 C28 179.7(2) . . . . ?
O2 C24 S2 C25 -16.9(3) . . . . ?
S2 C25 C26 C27 175.7(2) . . . . ?
S2 C25 C26 Cl3 -4.0(3) . . . . ?
S2 C25 C30 C29 -176.0(2) . . . . ?
S2 C25 C30 Cl4 4.2(3) . . . . ?

_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 2.028
_oxdiff_exptl_absorpt_empirical_full_min 0.385
####################################################################### 
# 
# 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_fyy-33
_database_code_depnum_ccdc_archive 'CCDC 2202642'
loop_
_audit_author_name
_audit_author_address
FYY
;Nanjing Forestry University
China
;
_audit_update_record             
;
2022-08-21 deposited with the CCDC.	2022-09-01 downloaded from the CCDC.
;
_audit_creation_date             2022-08-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 N2 O'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29
_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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.7192(2)
_cell_length_b                   10.2210(7)
_cell_length_c                   11.4399(8)
_cell_angle_alpha                79.456(6)
_cell_angle_beta                 89.714(5)
_cell_angle_gamma                76.365(5)
_cell_volume                     638.40(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3540
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      71.2450
_cell_measurement_theta_min      4.5250
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5417
_diffrn_reflns_point_group_measured_fraction_full 0.634
_diffrn_reflns_point_group_measured_fraction_max 0.616
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.550
_diffrn_reflns_theta_min         3.934
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     21.00  66.00   0.50    0.50    --   42.30 -57.00-120.00   90
  2  ω     88.00 128.00   0.50    0.50    --   42.30  77.00  90.00   80
  3  ω     26.00  59.00   0.50    0.50    --   42.30 -57.00   0.00   66
  4  ω    -22.00  61.00   0.50    0.50    --   42.30 -82.00-150.00  166
  5  ω    -39.00  15.00   0.50    0.50    --   42.30 -57.00-120.00  108
  6  ω     86.00 131.00   0.50    0.50    --   42.30  77.00 -60.00   90
  7  ω    -42.00  64.00   0.50    0.50    --   42.30 -57.00  60.00  212
  8  ω    -34.00  21.00   0.50    0.50    --   42.30 -57.00   0.00  110
  9  ω     51.00 132.00   0.50    0.50    --  101.60 -50.00   0.00  162
 10  ω     74.00 144.00   0.50    0.50    --  101.60 -82.00-120.00  140
 11  ω    139.00 191.00   0.50    0.50    --  101.60  50.00-180.00  104
 12  ω     30.00 145.00   0.50    0.50    --  101.60 -82.00   0.00  230
 13  ω     71.00 107.00   0.50    0.50    --  101.60  50.00-180.00   72
 14  ω     61.00 110.00   0.50    0.50    --  101.60 -82.00  90.00   98
 15  ω    104.00 140.00   0.50    0.50    --  101.60 -77.00-180.00   72
 16  ω     92.00 118.00   0.50    0.50    --  101.60 -82.00 -60.00   52
 17  ω     41.00 144.00   0.50    0.50    --  101.60 -82.00-150.00  206
 18  ω    142.00 168.00   0.50    0.50    --  101.60  82.00 -90.00   52
 19  ω     14.00 173.00   0.50    0.50    --  101.60 -25.00-180.00  318
 20  ω     24.00  60.00   0.50    0.50    --  101.60 -77.00-180.00   72
 21  ω     49.00 134.00   0.50    0.50    --  101.60 -82.00 150.00  170
 22  ω     87.00 127.00   0.50    0.50    --  101.60  82.00   0.00   80
 23  ω     74.00 191.00   0.50    0.50    --  101.60  12.00 -60.00  234
 24  ω     18.00  59.00   0.50    0.50    --  101.60  12.00 -60.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0543058000
_diffrn_orient_matrix_UB_12      0.0636723000
_diffrn_orient_matrix_UB_13      -0.1327292000
_diffrn_orient_matrix_UB_21      -0.2584230000
_diffrn_orient_matrix_UB_22      -0.0199428000
_diffrn_orient_matrix_UB_23      0.0113832000
_diffrn_orient_matrix_UB_31      -0.0849587000
_diffrn_orient_matrix_UB_32      0.1430923000
_diffrn_orient_matrix_UB_33      0.0323487000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.274
_reflns_Friedel_fraction_full    0.280
_reflns_Friedel_fraction_max     0.265
_reflns_number_gt                2873
_reflns_number_total             3054
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details 
;
 Flack x determined using 563 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.308
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         3054
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0868
_refine_ls_restrained_S_all      1.307
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2769
_refine_ls_wR_factor_ref         0.2790
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Rotating group:
 N2(H2A,H2B), N38(H38A,H38B)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C32(H32),
  C33(H33), C34(H34), C35(H35), C36(H36)
;
_atom_sites_solution_hydrogens   mixed
_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 -0.3033(7) 0.8710(4) 0.6316(4) 0.0317(10) Uani 1 1 d . . . . .
O37 O 0.6566(8) 0.4204(4) 0.3903(4) 0.0318(10) Uani 1 1 d . . . . .
N1 N -0.0646(9) 0.6956(5) 0.5573(5) 0.0278(11) Uani 1 1 d . . . . .
N2 N 0.1838(10) 0.5295(6) 0.4633(5) 0.0363(12) Uani 1 1 d . . . . .
H2A H 0.123803 0.458821 0.482020 0.044 Uiso 1 1 d R U . . .
H2B H 0.111253 0.580511 0.399040 0.044 Uiso 1 1 d R U . . .
N20 N 0.9319(8) 0.2205(5) 0.4622(4) 0.0234(10) Uani 1 1 d . . . . .
N38 N 1.2171(9) 0.0225(5) 0.5518(5) 0.0299(11) Uani 1 1 d . . . . .
H38A H 1.173500 0.047829 0.617826 0.036 Uiso 1 1 d R U . . .
H38B H 1.144663 -0.039000 0.539767 0.036 Uiso 1 1 d R U . . .
C1 C -0.1129(11) 0.7805(6) 0.6403(5) 0.0276(12) Uani 1 1 d . . . . .
C2 C 0.0699(12) 0.7596(6) 0.7338(6) 0.0309(13) Uani 1 1 d . . . . .
C3 C 0.2897(10) 0.6617(6) 0.7328(5) 0.0284(13) Uani 1 1 d . . . . .
C4 C 0.3279(11) 0.5835(7) 0.6415(6) 0.0308(13) Uani 1 1 d . . . . .
H4 H 0.472051 0.518423 0.641037 0.037 Uiso 1 1 calc R U . . .
C5 C 0.1563(10) 0.6025(5) 0.5544(5) 0.0288(13) Uani 1 1 d . . . . .
C6 C 0.0307(12) 0.8392(7) 0.8223(6) 0.0354(14) Uani 1 1 d . . . . .
H6 H -0.115888 0.902312 0.822700 0.042 Uiso 1 1 calc R U . . .
C7 C 0.2053(14) 0.8260(8) 0.9087(6) 0.0426(16) Uani 1 1 d . . . . .
H7 H 0.177043 0.879668 0.967103 0.051 Uiso 1 1 calc R U . . .
C8 C 0.4263(14) 0.7308(8) 0.9082(7) 0.0435(16) Uani 1 1 d . . . . .
H8 H 0.545390 0.722294 0.966036 0.052 Uiso 1 1 calc R U . . .
C9 C 0.4693(11) 0.6488(7) 0.8219(7) 0.0374(16) Uani 1 1 d . . . . .
H9 H 0.616066 0.585459 0.822833 0.045 Uiso 1 1 calc R U . . .
C10 C -0.2557(11) 0.7116(6) 0.4660(6) 0.0318(13) Uani 1 1 d . . . . .
H10A H -0.410327 0.746833 0.498048 0.038 Uiso 1 1 calc R U . . .
H10B H -0.255474 0.622092 0.448786 0.038 Uiso 1 1 calc R U . . .
C11 C -0.2287(11) 0.8063(6) 0.3511(6) 0.0309(13) Uani 1 1 d . . . . .
C12 C -0.3817(13) 0.8188(8) 0.2535(7) 0.0426(17) Uani 1 1 d . . . . .
H12 H -0.498874 0.768681 0.259830 0.051 Uiso 1 1 calc R U . . .
C13 C -0.3628(15) 0.9040(9) 0.1477(7) 0.054(2) Uani 1 1 d . . . . .
H13 H -0.468864 0.911875 0.084003 0.064 Uiso 1 1 calc R U . . .
C14 C -0.1893(15) 0.9775(8) 0.1350(6) 0.0468(18) Uani 1 1 d . . . . .
H14 H -0.175195 1.033584 0.062800 0.056 Uiso 1 1 calc R U . . .
C15 C -0.0343(13) 0.9672(8) 0.2317(6) 0.0392(15) Uani 1 1 d . . . . .
H15 H 0.082477 1.017624 0.224566 0.047 Uiso 1 1 calc R U . . .
C16 C -0.0539(12) 0.8822(7) 0.3380(6) 0.0336(13) Uani 1 1 d . . . . .
H16 H 0.050970 0.875487 0.401928 0.040 Uiso 1 1 calc R U . . .
C21 C 0.8512(10) 0.3403(6) 0.3776(5) 0.0232(11) Uani 1 1 d . . . . .
C22 C 1.0054(10) 0.3630(6) 0.2779(5) 0.0247(12) Uani 1 1 d . . . . .
C23 C 0.9264(12) 0.4796(7) 0.1879(6) 0.0336(14) Uani 1 1 d . . . . .
H23 H 0.775611 0.537895 0.190873 0.040 Uiso 1 1 calc R U . . .
C24 C 1.0735(14) 0.5066(7) 0.0958(6) 0.0403(16) Uani 1 1 d . . . . .
H24 H 1.022716 0.583213 0.035977 0.048 Uiso 1 1 calc R U . . .
C25 C 1.3013(14) 0.4176(8) 0.0927(6) 0.0399(15) Uani 1 1 d . . . . .
H25 H 1.400524 0.436387 0.030365 0.048 Uiso 1 1 calc R U . . .
C26 C 1.3799(12) 0.3043(7) 0.1792(6) 0.0346(14) Uani 1 1 d . . . . .
H26 H 1.531380 0.247149 0.175261 0.042 Uiso 1 1 calc R U . . .
C27 C 1.2312(10) 0.2730(6) 0.2755(5) 0.0253(12) Uani 1 1 d . . . . .
C28 C 1.3070(10) 0.1578(6) 0.3695(5) 0.0278(12) Uani 1 1 d . . . . .
H28 H 1.457974 0.098858 0.368813 0.033 Uiso 1 1 calc R U . . .
C29 C 1.1596(10) 0.1341(6) 0.4600(5) 0.0260(12) Uani 1 1 d . . . . .
C30 C 0.7623(10) 0.1879(6) 0.5530(5) 0.0262(12) Uani 1 1 d . . . . .
H30A H 0.776872 0.089773 0.567824 0.031 Uiso 1 1 calc R U . . .
H30B H 0.599987 0.232055 0.521553 0.031 Uiso 1 1 calc R U . . .
C31 C 0.7969(10) 0.2312(6) 0.6708(5) 0.0251(11) Uani 1 1 d . . . . .
C32 C 0.6422(10) 0.2015(6) 0.7620(5) 0.0293(13) Uani 1 1 d . . . . .
H32 H 0.523560 0.156991 0.748250 0.035 Uiso 1 1 calc R U . . .
C33 C 0.6615(12) 0.2363(8) 0.8695(6) 0.0380(15) Uani 1 1 d . . . . .
H33 H 0.556327 0.215553 0.928359 0.046 Uiso 1 1 calc R U . . .
C34 C 0.8366(14) 0.3025(7) 0.8925(6) 0.0392(15) Uani 1 1 d . . . . .
H34 H 0.849473 0.326094 0.966554 0.047 Uiso 1 1 calc R U . . .
C35 C 0.9950(12) 0.3336(7) 0.8028(6) 0.0329(13) Uani 1 1 d . . . . .
H35 H 1.114644 0.377058 0.817432 0.039 Uiso 1 1 calc R U . . .
C36 C 0.9713(11) 0.2991(6) 0.6922(5) 0.0293(12) Uani 1 1 d . . . . .
H36 H 1.072949 0.321558 0.632150 0.035 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.242(7) . ?
O37 C21 1.242(7) . ?
N1 C1 1.385(8) . ?
N1 C5 1.395(8) . ?
N1 C10 1.475(8) . ?
N2 H2A 0.8632 . ?
N2 H2B 0.8633 . ?
N2 C5 1.376(8) . ?
N20 C21 1.397(7) . ?
N20 C29 1.394(7) . ?
N20 C30 1.465(7) . ?
N38 H38A 0.8601 . ?
N38 H38B 0.8602 . ?
N38 C29 1.379(7) . ?
C1 C2 1.450(9) . ?
C2 C3 1.412(9) . ?
C2 C6 1.397(10) . ?
C3 C4 1.414(9) . ?
C3 C9 1.418(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.357(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.375(10) . ?
C7 H7 0.9300 . ?
C7 C8 1.402(11) . ?
C8 H8 0.9300 . ?
C8 C9 1.392(11) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.515(9) . ?
C11 C12 1.390(9) . ?
C11 C16 1.395(9) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(12) . ?
C13 H13 0.9300 . ?
C13 C14 1.371(13) . ?
C14 H14 0.9300 . ?
C14 C15 1.394(10) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(9) . ?
C16 H16 0.9300 . ?
C21 C22 1.456(8) . ?
C22 C23 1.409(8) . ?
C22 C27 1.401(8) . ?
C23 H23 0.9300 . ?
C23 C24 1.374(9) . ?
C24 H24 0.9300 . ?
C24 C25 1.407(10) . ?
C25 H25 0.9300 . ?
C25 C26 1.364(10) . ?
C26 H26 0.9300 . ?
C26 C27 1.425(8) . ?
C27 C28 1.425(8) . ?
C28 H28 0.9300 . ?
C28 C29 1.355(9) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.521(8) . ?
C31 C32 1.401(8) . ?
C31 C36 1.388(8) . ?
C32 H32 0.9300 . ?
C32 C33 1.353(10) . ?
C33 H33 0.9300 . ?
C33 C34 1.385(11) . ?
C34 H34 0.9300 . ?
C34 C35 1.408(10) . ?
C35 H35 0.9300 . ?
C35 C36 1.390(9) . ?
C36 H36 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
C1 N1 C5 122.9(5) . . ?
C1 N1 C10 116.9(5) . . ?
C5 N1 C10 120.1(5) . . ?
H2A N2 H2B 109.2 . . ?
C5 N2 H2A 110.0 . . ?
C5 N2 H2B 110.1 . . ?
C21 N20 C30 116.5(5) . . ?
C29 N20 C21 122.3(5) . . ?
C29 N20 C30 121.1(5) . . ?
H38A N38 H38B 109.5 . . ?
C29 N38 H38A 109.5 . . ?
C29 N38 H38B 109.9 . . ?
O1 C1 N1 120.2(5) . . ?
O1 C1 C2 123.0(5) . . ?
N1 C1 C2 116.8(5) . . ?
C3 C2 C1 119.8(6) . . ?
C6 C2 C1 119.9(6) . . ?
C6 C2 C3 120.3(6) . . ?
C2 C3 C4 119.5(5) . . ?
C2 C3 C9 118.3(6) . . ?
C4 C3 C9 122.1(6) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.7(6) . . ?
C5 C4 H4 119.7 . . ?
N2 C5 N1 116.8(5) . . ?
C4 C5 N1 120.0(5) . . ?
C4 C5 N2 123.2(6) . . ?
C2 C6 H6 119.5 . . ?
C7 C6 C2 121.1(6) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.5(7) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.7(6) . . ?
C9 C8 H8 119.7 . . ?
C3 C9 H9 120.0 . . ?
C8 C9 C3 120.1(6) . . ?
C8 C9 H9 120.0 . . ?
N1 C10 H10A 108.8 . . ?
N1 C10 H10B 108.8 . . ?
N1 C10 C11 113.8(5) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C12 C11 C10 119.6(6) . . ?
C12 C11 C16 117.8(6) . . ?
C16 C11 C10 122.6(5) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.2(7) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.7(6) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.2(7) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(7) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 120.9(6) . . ?
C15 C16 H16 119.5 . . ?
O37 C21 N20 119.6(5) . . ?
O37 C21 C22 123.8(5) . . ?
N20 C21 C22 116.6(5) . . ?
C23 C22 C21 118.5(5) . . ?
C27 C22 C21 119.9(5) . . ?
C27 C22 C23 121.5(5) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.6(6) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.5(6) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 119.3 . . ?
C26 C25 C24 121.4(6) . . ?
C26 C25 H25 119.3 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.4(6) . . ?
C27 C26 H26 119.8 . . ?
C22 C27 C26 117.6(5) . . ?
C22 C27 C28 119.8(5) . . ?
C26 C27 C28 122.6(6) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 120.1(5) . . ?
C29 C28 H28 120.0 . . ?
N38 C29 N20 115.7(5) . . ?
C28 C29 N20 120.8(5) . . ?
C28 C29 N38 123.4(5) . . ?
N20 C30 H30A 108.5 . . ?
N20 C30 H30B 108.5 . . ?
N20 C30 C31 115.0(4) . . ?
H30A C30 H30B 107.5 . . ?
C31 C30 H30A 108.5 . . ?
C31 C30 H30B 108.5 . . ?
C32 C31 C30 117.8(5) . . ?
C36 C31 C30 123.6(5) . . ?
C36 C31 C32 118.6(5) . . ?
C31 C32 H32 119.3 . . ?
C33 C32 C31 121.4(6) . . ?
C33 C32 H32 119.3 . . ?
C32 C33 H33 119.7 . . ?
C32 C33 C34 120.6(6) . . ?
C34 C33 H33 119.7 . . ?
C33 C34 H34 120.3 . . ?
C33 C34 C35 119.4(6) . . ?
C35 C34 H34 120.3 . . ?
C34 C35 H35 120.2 . . ?
C36 C35 C34 119.5(6) . . ?
C36 C35 H35 120.2 . . ?
C31 C36 C35 120.5(5) . . ?
C31 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -175.2(5) . . . . ?
O1 C1 C2 C6 2.9(8) . . . . ?
O37 C21 C22 C23 -2.6(8) . . . . ?
O37 C21 C22 C27 174.8(5) . . . . ?
N1 C1 C2 C3 3.6(7) . . . . ?
N1 C1 C2 C6 -178.4(5) . . . . ?
N1 C10 C11 C12 173.2(6) . . . . ?
N1 C10 C11 C16 -6.5(9) . . . . ?
N20 C21 C22 C23 177.4(5) . . . . ?
N20 C21 C22 C27 -5.2(7) . . . . ?
N20 C30 C31 C32 -179.3(5) . . . . ?
N20 C30 C31 C36 1.3(8) . . . . ?
C1 N1 C5 N2 -176.7(5) . . . . ?
C1 N1 C5 C4 5.8(8) . . . . ?
C1 N1 C10 C11 94.6(6) . . . . ?
C1 C2 C3 C4 -0.9(8) . . . . ?
C1 C2 C3 C9 176.8(5) . . . . ?
C1 C2 C6 C7 -177.0(6) . . . . ?
C2 C3 C4 C5 0.5(8) . . . . ?
C2 C3 C9 C8 0.5(8) . . . . ?
C2 C6 C7 C8 -0.1(10) . . . . ?
C3 C2 C6 C7 1.1(9) . . . . ?
C3 C4 C5 N1 -2.8(8) . . . . ?
C3 C4 C5 N2 179.9(5) . . . . ?
C4 C3 C9 C8 178.1(6) . . . . ?
C5 N1 C1 O1 172.8(5) . . . . ?
C5 N1 C1 C2 -6.0(7) . . . . ?
C5 N1 C10 C11 -82.7(6) . . . . ?
C6 C2 C3 C4 -179.0(5) . . . . ?
C6 C2 C3 C9 -1.2(8) . . . . ?
C6 C7 C8 C9 -0.7(11) . . . . ?
C7 C8 C9 C3 0.5(10) . . . . ?
C9 C3 C4 C5 -177.1(5) . . . . ?
C10 N1 C1 O1 -4.5(7) . . . . ?
C10 N1 C1 C2 176.7(5) . . . . ?
C10 N1 C5 N2 0.4(7) . . . . ?
C10 N1 C5 C4 -177.1(5) . . . . ?
C10 C11 C12 C13 179.9(7) . . . . ?
C10 C11 C16 C15 179.8(7) . . . . ?
C11 C12 C13 C14 1.1(12) . . . . ?
C12 C11 C16 C15 0.2(10) . . . . ?
C12 C13 C14 C15 -1.3(12) . . . . ?
C13 C14 C15 C16 1.0(12) . . . . ?
C14 C15 C16 C11 -0.4(11) . . . . ?
C16 C11 C12 C13 -0.5(10) . . . . ?
C21 N20 C29 N38 177.7(5) . . . . ?
C21 N20 C29 C28 -4.9(8) . . . . ?
C21 N20 C30 C31 -97.5(5) . . . . ?
C21 C22 C23 C24 177.0(6) . . . . ?
C21 C22 C27 C26 -176.7(5) . . . . ?
C21 C22 C27 C28 1.3(7) . . . . ?
C22 C23 C24 C25 -0.1(10) . . . . ?
C22 C27 C28 C29 1.1(8) . . . . ?
C23 C22 C27 C26 0.6(8) . . . . ?
C23 C22 C27 C28 178.6(5) . . . . ?
C23 C24 C25 C26 0.2(10) . . . . ?
C24 C25 C26 C27 0.1(10) . . . . ?
C25 C26 C27 C22 -0.5(9) . . . . ?
C25 C26 C27 C28 -178.5(6) . . . . ?
C26 C27 C28 C29 179.0(5) . . . . ?
C27 C22 C23 C24 -0.3(9) . . . . ?
C27 C28 C29 N20 0.6(8) . . . . ?
C27 C28 C29 N38 177.8(5) . . . . ?
C29 N20 C21 O37 -172.9(5) . . . . ?
C29 N20 C21 C22 7.0(7) . . . . ?
C29 N20 C30 C31 83.8(6) . . . . ?
C30 N20 C21 O37 8.4(7) . . . . ?
C30 N20 C21 C22 -171.7(4) . . . . ?
C30 N20 C29 N38 -3.7(7) . . . . ?
C30 N20 C29 C28 173.7(5) . . . . ?
C30 C31 C32 C33 179.8(6) . . . . ?
C30 C31 C36 C35 -179.0(6) . . . . ?
C31 C32 C33 C34 -0.1(10) . . . . ?
C32 C31 C36 C35 1.6(9) . . . . ?
C32 C33 C34 C35 0.1(10) . . . . ?
C33 C34 C35 C36 0.8(10) . . . . ?
C34 C35 C36 C31 -1.6(10) . . . . ?
C36 C31 C32 C33 -0.7(9) . . . . ?


_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 2.475
_oxdiff_exptl_absorpt_empirical_full_min 0.572
