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

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

data_aaaa
_database_code_depnum_ccdc_archive 'CCDC 2143807'
loop_
_audit_author_name
_audit_author_address
'Peng-Ju Xia'
;Guangxi normal university
China
;
_audit_update_record             
;
2022-01-22 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_audit_creation_date             2022-01-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C35 H26 F3 N O'
_chemical_formula_sum            'C35 H27 F3 N O'
_chemical_formula_weight         534.57
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N F'
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'
F F 0.0171 0.0103 '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                   12.1957(6)
_cell_length_b                   14.1964(6)
_cell_length_c                   16.4452(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.807(5)
_cell_angle_gamma                90
_cell_volume                     2837.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3493
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.8190
_cell_measurement_theta_min      3.7640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1116
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11136
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.889
_diffrn_reflns_theta_min         3.353
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00   4.00   1.00   29.81    --  -17.23 -57.00  90.00   90
  2  ω    -61.00  56.00   1.00   29.81    --  -17.23  19.00  90.00  117
  3  ω    -42.00  13.00   1.00   29.81    --  -17.23 -77.00   0.00   55
  4  ω     39.00  82.00   1.00   29.81    --   15.20 178.00   0.00   43
  5  ω     37.00  55.00   1.00   29.81    --   15.20-178.00 -90.00   18
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0505515000
_diffrn_orient_matrix_UB_12      0.0051086000
_diffrn_orient_matrix_UB_13      -0.0178989000
_diffrn_orient_matrix_UB_21      -0.0286001000
_diffrn_orient_matrix_UB_22      -0.0008695000
_diffrn_orient_matrix_UB_23      -0.0394222000
_diffrn_orient_matrix_UB_31      -0.0057187000
_diffrn_orient_matrix_UB_32      0.0496722000
_diffrn_orient_matrix_UB_33      0.0011590000
_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                2929
_reflns_number_total             5680
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.881
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5680
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1522
_refine_ls_R_factor_gt           0.0780
_refine_ls_restrained_S_all      1.069
_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)+(0.1532P)²+1.8128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2431
_refine_ls_wR_factor_ref         0.3311
_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:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C28(H28), C29(H29), C25(H25), C31(H31), C3(H3), C32(H32), C5(H5),
 C35(H35), C19(H19), C6(H6), C33(H33), C23(H23), C13(H13), C2(H2), C34(H34),
 C20(H20), C22(H22), C14(H14), C21(H21), C15(H15), C16(H16), C17(H17), C1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F1 F 0.4982(2) 0.26671(17) 0.11488(16) 0.0763(7) Uani 1 1 d . . . . .
F2 F 0.4102(2) 0.23139(19) 0.21769(16) 0.0801(8) Uani 1 1 d . . . . .
F3 F 0.5295(2) 0.13515(16) 0.17663(17) 0.0815(8) Uani 1 1 d . . . . .
N1 N 0.5637(3) 0.3707(2) 0.2507(2) 0.0565(8) Uani 1 1 d . . . . .
O1 O 0.7276(3) 0.4101(2) 0.1344(2) 0.0934(11) Uani 1 1 d . . . . .
C24 C 0.6107(3) 0.2215(2) 0.3277(2) 0.0543(9) Uani 1 1 d . . . . .
C27 C 0.6263(3) 0.1364(3) 0.4839(2) 0.0600(10) Uani 1 1 d . . . . .
C30 C 0.6366(4) 0.0953(3) 0.5671(2) 0.0610(10) Uani 1 1 d . . . . .
C4 C 0.7222(3) 0.2816(3) 0.0452(2) 0.0588(10) Uani 1 1 d . . . . .
C26 C 0.5338(3) 0.1874(3) 0.4546(2) 0.0618(10) Uani 1 1 d . . . . .
H26 H 0.475213 0.192983 0.486965 0.074 Uiso 1 1 calc R U . . .
C28 C 0.7083(4) 0.1261(3) 0.4309(3) 0.0650(11) Uani 1 1 d . . . . .
H28 H 0.770560 0.090993 0.447513 0.078 Uiso 1 1 calc R U . . .
C29 C 0.7002(3) 0.1663(3) 0.3543(3) 0.0630(10) Uani 1 1 d . . . . .
H29 H 0.755856 0.156182 0.319917 0.076 Uiso 1 1 calc R U . . .
C9 C 0.6012(3) 0.2728(2) 0.2457(2) 0.0551(9) Uani 1 1 d . . . . .
C25 C 0.5265(3) 0.2296(3) 0.3793(2) 0.0595(10) Uani 1 1 d . . . . .
H25 H 0.464024 0.264293 0.362518 0.071 Uiso 1 1 calc R U . . .
C11 C 0.6104(3) 0.4313(3) 0.3000(3) 0.0601(10) Uani 1 1 d . . . . .
C8 C 0.7089(3) 0.2656(3) 0.2025(2) 0.0603(10) Uani 1 1 d . . . . .
H8A H 0.769605 0.281920 0.241846 0.072 Uiso 1 1 calc R U . . .
H8B H 0.718662 0.200176 0.187529 0.072 Uiso 1 1 calc R U . . .
C10 C 0.5099(4) 0.2274(3) 0.1892(3) 0.0623(10) Uani 1 1 d . . . . .
C18 C 0.7078(3) 0.4190(3) 0.3597(3) 0.0621(10) Uani 1 1 d . . . . .
C31 C 0.5457(4) 0.0572(3) 0.6010(3) 0.0731(12) Uani 1 1 d . . . . .
H31 H 0.477362 0.057916 0.571270 0.088 Uiso 1 1 calc R U . . .
C7 C 0.7185(4) 0.3251(3) 0.1269(3) 0.0673(11) Uani 1 1 d . . . . .
C3 C 0.7380(3) 0.3394(3) -0.0214(3) 0.0699(12) Uani 1 1 d . . . . .
H3 H 0.744445 0.404083 -0.013693 0.084 Uiso 1 1 calc R U . . .
C12 C 0.5650(3) 0.5293(3) 0.2917(3) 0.0696(12) Uani 1 1 d . . . . .
C32 C 0.5556(5) 0.0185(3) 0.6778(3) 0.0846(15) Uani 1 1 d . . . . .
H32 H 0.493847 -0.006648 0.699323 0.102 Uiso 1 1 calc R U . . .
C5 C 0.7137(4) 0.1855(3) 0.0307(3) 0.0750(12) Uani 1 1 d . . . . .
H5 H 0.703729 0.144604 0.073596 0.090 Uiso 1 1 calc R U . . .
C35 C 0.7378(4) 0.0930(3) 0.6140(3) 0.0780(13) Uani 1 1 d . . . . .
H35 H 0.799671 0.118433 0.592815 0.094 Uiso 1 1 calc R U . . .
C19 C 0.8129(4) 0.4358(3) 0.3346(3) 0.0742(12) Uani 1 1 d . . . . .
H19 H 0.820292 0.454338 0.281063 0.089 Uiso 1 1 calc R U . . .
C6 C 0.7202(4) 0.1498(4) -0.0479(3) 0.0812(13) Uani 1 1 d . . . . .
H6 H 0.713908 0.085331 -0.057255 0.097 Uiso 1 1 calc R U . . .
C33 C 0.6561(5) 0.0165(3) 0.7235(3) 0.0861(15) Uani 1 1 d . . . . .
H33 H 0.662061 -0.009473 0.775633 0.103 Uiso 1 1 calc R U . . .
C23 C 0.6989(5) 0.3937(3) 0.4401(3) 0.0820(14) Uani 1 1 d . . . . .
H23 H 0.629884 0.383709 0.458705 0.098 Uiso 1 1 calc R U . . .
C13 C 0.5404(4) 0.5669(3) 0.2139(3) 0.0797(14) Uani 1 1 d . . . . .
H13 H 0.550036 0.530644 0.167988 0.096 Uiso 1 1 calc R U . . .
C2 C 0.7442(4) 0.3027(4) -0.0982(3) 0.0807(14) Uani 1 1 d . . . . .
H2 H 0.754455 0.342827 -0.141602 0.097 Uiso 1 1 calc R U . . .
C34 C 0.7477(5) 0.0536(4) 0.6909(3) 0.0856(14) Uani 1 1 d . . . . .
H34 H 0.815828 0.051974 0.720814 0.103 Uiso 1 1 calc R U . . .
C20 C 0.9051(4) 0.4254(4) 0.3874(4) 0.0982(17) Uani 1 1 d . . . . .
H20 H 0.974157 0.436665 0.369405 0.118 Uiso 1 1 calc R U . . .
C22 C 0.7940(6) 0.3831(4) 0.4938(4) 0.1013(19) Uani 1 1 d . . . . .
H22 H 0.788012 0.365626 0.547747 0.122 Uiso 1 1 calc R U . . .
C14 C 0.5010(4) 0.6597(4) 0.2051(5) 0.106(2) Uani 1 1 d . . . . .
H14 H 0.488340 0.686153 0.153434 0.127 Uiso 1 1 calc R U . . .
C21 C 0.8961(5) 0.3986(4) 0.4663(4) 0.1009(18) Uani 1 1 d . . . . .
H21 H 0.959095 0.390865 0.501592 0.121 Uiso 1 1 calc R U . . .
C15 C 0.4816(6) 0.7104(4) 0.2723(6) 0.134(3) Uani 1 1 d . . . . .
H15 H 0.449830 0.769821 0.266514 0.161 Uiso 1 1 calc R U . . .
C16 C 0.5082(7) 0.6752(5) 0.3473(5) 0.136(3) Uani 1 1 d . . . . .
H16 H 0.498166 0.711501 0.393222 0.164 Uiso 1 1 calc R U . . .
C17 C 0.5505(5) 0.5848(4) 0.3562(4) 0.115(2) Uani 1 1 d . . . . .
H17 H 0.569587 0.561759 0.408435 0.138 Uiso 1 1 calc R U . . .
C1 C 0.7356(4) 0.2096(4) -0.1110(3) 0.0824(14) Uani 1 1 d . . . . .
H1 H 0.740192 0.185536 -0.163204 0.099 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
F1 C10 1.340(5) . ?
F2 C10 1.340(5) . ?
F3 C10 1.351(4) . ?
N1 C9 1.467(5) . ?
N1 C11 1.282(5) . ?
O1 C7 1.217(5) . ?
C24 C29 1.385(5) . ?
C24 C9 1.528(5) . ?
C24 C25 1.391(5) . ?
C27 C30 1.482(6) . ?
C27 C26 1.392(6) . ?
C27 C28 1.389(5) . ?
C30 C31 1.392(6) . ?
C30 C35 1.400(6) . ?
C4 C7 1.484(6) . ?
C4 C3 1.395(5) . ?
C4 C5 1.387(6) . ?
C26 H26 0.9300 . ?
C26 C25 1.370(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.379(6) . ?
C29 H29 0.9300 . ?
C9 C8 1.549(5) . ?
C9 C10 1.531(6) . ?
C25 H25 0.9300 . ?
C11 C18 1.487(6) . ?
C11 C12 1.499(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.516(5) . ?
C18 C19 1.400(6) . ?
C18 C23 1.383(6) . ?
C31 H31 0.9300 . ?
C31 C32 1.373(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.373(7) . ?
C12 C13 1.395(7) . ?
C12 C17 1.345(7) . ?
C32 H32 0.9300 . ?
C32 C33 1.385(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.397(6) . ?
C35 H35 0.9300 . ?
C35 C34 1.379(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.369(7) . ?
C6 H6 0.9300 . ?
C6 C1 1.365(7) . ?
C33 H33 0.9300 . ?
C33 C34 1.382(7) . ?
C23 H23 0.9300 . ?
C23 C22 1.405(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.405(7) . ?
C2 H2 0.9300 . ?
C2 C1 1.342(7) . ?
C34 H34 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.365(8) . ?
C22 H22 0.9300 . ?
C22 C21 1.378(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.357(10) . ?
C21 H21 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.345(10) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(8) . ?
C17 H17 0.9300 . ?
C1 H1 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
C11 N1 C9 123.2(3) . . ?
C29 C24 C9 123.3(3) . . ?
C29 C24 C25 117.1(4) . . ?
C25 C24 C9 119.6(3) . . ?
C26 C27 C30 121.9(4) . . ?
C28 C27 C30 121.9(4) . . ?
C28 C27 C26 116.3(4) . . ?
C31 C30 C27 121.0(4) . . ?
C31 C30 C35 117.7(4) . . ?
C35 C30 C27 121.4(4) . . ?
C3 C4 C7 118.9(4) . . ?
C5 C4 C7 123.9(4) . . ?
C5 C4 C3 117.2(4) . . ?
C27 C26 H26 119.0 . . ?
C25 C26 C27 122.0(4) . . ?
C25 C26 H26 119.0 . . ?
C27 C28 H28 119.0 . . ?
C29 C28 C27 122.0(4) . . ?
C29 C28 H28 119.0 . . ?
C24 C29 H29 119.4 . . ?
C28 C29 C24 121.1(4) . . ?
C28 C29 H29 119.4 . . ?
N1 C9 C24 113.8(3) . . ?
N1 C9 C8 111.6(3) . . ?
N1 C9 C10 102.6(3) . . ?
C24 C9 C8 111.6(3) . . ?
C24 C9 C10 109.4(3) . . ?
C10 C9 C8 107.1(3) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 C24 121.3(4) . . ?
C26 C25 H25 119.3 . . ?
N1 C11 C18 128.8(4) . . ?
N1 C11 C12 115.1(4) . . ?
C18 C11 C12 115.9(3) . . ?
C9 C8 H8A 107.9 . . ?
C9 C8 H8B 107.9 . . ?
H8A C8 H8B 107.2 . . ?
C7 C8 C9 117.7(3) . . ?
C7 C8 H8A 107.9 . . ?
C7 C8 H8B 107.9 . . ?
F1 C10 F2 105.7(3) . . ?
F1 C10 F3 105.7(3) . . ?
F1 C10 C9 113.2(3) . . ?
F2 C10 F3 105.7(3) . . ?
F2 C10 C9 113.9(3) . . ?
F3 C10 C9 111.9(4) . . ?
C19 C18 C11 119.0(4) . . ?
C23 C18 C11 122.7(4) . . ?
C23 C18 C19 118.3(4) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 C30 120.9(5) . . ?
C32 C31 H31 119.6 . . ?
O1 C7 C4 119.7(4) . . ?
O1 C7 C8 118.9(4) . . ?
C4 C7 C8 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 C4 121.4(4) . . ?
C2 C3 H3 119.3 . . ?
C13 C12 C11 119.2(4) . . ?
C17 C12 C11 122.9(5) . . ?
C17 C12 C13 117.8(5) . . ?
C31 C32 H32 119.5 . . ?
C31 C32 C33 120.9(5) . . ?
C33 C32 H32 119.5 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(4) . . ?
C6 C5 H5 119.8 . . ?
C30 C35 H35 119.3 . . ?
C34 C35 C30 121.3(5) . . ?
C34 C35 H35 119.3 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.1(5) . . ?
C20 C19 H19 119.4 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 C5 120.0(5) . . ?
C1 C6 H6 120.0 . . ?
C32 C33 H33 120.4 . . ?
C34 C33 C32 119.2(5) . . ?
C34 C33 H33 120.4 . . ?
C18 C23 H23 120.0 . . ?
C18 C23 C22 120.1(5) . . ?
C22 C23 H23 120.0 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(5) . . ?
C14 C13 H13 120.0 . . ?
C3 C2 H2 119.7 . . ?
C1 C2 C3 120.5(4) . . ?
C1 C2 H2 119.7 . . ?
C35 C34 C33 120.0(5) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.4(6) . . ?
C21 C20 H20 119.8 . . ?
C23 C22 H22 120.1 . . ?
C21 C22 C23 119.8(6) . . ?
C21 C22 H22 120.1 . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.6(6) . . ?
C15 C14 H14 120.2 . . ?
C20 C21 C22 120.2(5) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(6) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 119.9(6) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 122.1(7) . . ?
C12 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C6 C1 H1 119.8 . . ?
C2 C1 C6 120.5(5) . . ?
C2 C1 H1 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
N1 C9 C8 C7 -42.3(5) . . . . ?
N1 C9 C10 F1 60.6(4) . . . . ?
N1 C9 C10 F2 -60.2(4) . . . . ?
N1 C9 C10 F3 180.0(3) . . . . ?
N1 C11 C18 C19 89.3(5) . . . . ?
N1 C11 C18 C23 -92.3(6) . . . . ?
N1 C11 C12 C13 -42.8(6) . . . . ?
N1 C11 C12 C17 139.9(5) . . . . ?
C24 C9 C8 C7 -170.9(3) . . . . ?
C24 C9 C10 F1 -178.2(3) . . . . ?
C24 C9 C10 F2 61.0(4) . . . . ?
C24 C9 C10 F3 -58.8(4) . . . . ?
C27 C30 C31 C32 179.5(4) . . . . ?
C27 C30 C35 C34 -179.1(4) . . . . ?
C27 C26 C25 C24 1.6(6) . . . . ?
C27 C28 C29 C24 1.9(6) . . . . ?
C30 C27 C26 C25 176.6(3) . . . . ?
C30 C27 C28 C29 -178.3(4) . . . . ?
C30 C31 C32 C33 0.1(7) . . . . ?
C30 C35 C34 C33 -0.8(7) . . . . ?
C4 C3 C2 C1 -0.3(7) . . . . ?
C4 C5 C6 C1 0.4(7) . . . . ?
C26 C27 C30 C31 37.3(5) . . . . ?
C26 C27 C30 C35 -143.1(4) . . . . ?
C26 C27 C28 C29 1.8(6) . . . . ?
C28 C27 C30 C31 -142.6(4) . . . . ?
C28 C27 C30 C35 37.0(6) . . . . ?
C28 C27 C26 C25 -3.5(6) . . . . ?
C29 C24 C9 N1 -134.6(4) . . . . ?
C29 C24 C9 C8 -7.2(5) . . . . ?
C29 C24 C9 C10 111.2(4) . . . . ?
C29 C24 C25 C26 2.2(6) . . . . ?
C9 N1 C11 C18 0.6(7) . . . . ?
C9 N1 C11 C12 175.8(3) . . . . ?
C9 C24 C29 C28 175.9(4) . . . . ?
C9 C24 C25 C26 -177.6(3) . . . . ?
C9 C8 C7 O1 70.2(5) . . . . ?
C9 C8 C7 C4 -112.8(4) . . . . ?
C25 C24 C29 C28 -3.9(6) . . . . ?
C25 C24 C9 N1 45.2(5) . . . . ?
C25 C24 C9 C8 172.6(3) . . . . ?
C25 C24 C9 C10 -69.0(4) . . . . ?
C11 N1 C9 C24 53.5(5) . . . . ?
C11 N1 C9 C8 -74.0(5) . . . . ?
C11 N1 C9 C10 171.6(4) . . . . ?
C11 C18 C19 C20 -180.0(4) . . . . ?
C11 C18 C23 C22 180.0(4) . . . . ?
C11 C12 C13 C14 -178.0(4) . . . . ?
C11 C12 C17 C16 -179.9(6) . . . . ?
C8 C9 C10 F1 -57.0(4) . . . . ?
C8 C9 C10 F2 -177.9(3) . . . . ?
C8 C9 C10 F3 62.3(4) . . . . ?
C10 C9 C8 C7 69.4(4) . . . . ?
C18 C11 C12 C13 133.0(4) . . . . ?
C18 C11 C12 C17 -44.3(7) . . . . ?
C18 C19 C20 C21 -0.3(8) . . . . ?
C18 C23 C22 C21 0.5(8) . . . . ?
C31 C30 C35 C34 0.5(6) . . . . ?
C31 C32 C33 C34 -0.4(7) . . . . ?
C7 C4 C3 C2 178.8(4) . . . . ?
C7 C4 C5 C6 -178.8(4) . . . . ?
C3 C4 C7 O1 1.0(6) . . . . ?
C3 C4 C7 C8 -176.0(4) . . . . ?
C3 C4 C5 C6 -0.5(7) . . . . ?
C3 C2 C1 C6 0.2(7) . . . . ?
C12 C11 C18 C19 -85.9(5) . . . . ?
C12 C11 C18 C23 92.6(5) . . . . ?
C12 C13 C14 C15 -3.5(8) . . . . ?
C32 C33 C34 C35 0.7(7) . . . . ?
C5 C4 C7 O1 179.2(4) . . . . ?
C5 C4 C7 C8 2.2(6) . . . . ?
C5 C4 C3 C2 0.4(6) . . . . ?
C5 C6 C1 C2 -0.3(8) . . . . ?
C35 C30 C31 C32 -0.1(6) . . . . ?
C19 C18 C23 C22 -1.6(7) . . . . ?
C19 C20 C21 C22 -0.9(9) . . . . ?
C23 C18 C19 C20 1.5(7) . . . . ?
C23 C22 C21 C20 0.8(9) . . . . ?
C13 C12 C17 C16 2.8(9) . . . . ?
C13 C14 C15 C16 5.4(11) . . . . ?
C14 C15 C16 C17 -3.2(12) . . . . ?
C15 C16 C17 C12 -1.0(12) . . . . ?
C17 C12 C13 C14 -0.6(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.408
_oxdiff_exptl_absorpt_empirical_full_min 0.814
####################################################################### 
# 
# 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_20211221-xpj_autoaaa
_database_code_depnum_ccdc_archive 'CCDC 2143808'
loop_
_audit_author_name
_audit_author_address
'Peng-Ju Xia'
;Guangxi normal university
China
;
_audit_update_record             
;
2022-01-22 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_audit_creation_date             2021-12-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H31 N O2'
_chemical_formula_sum            'C32 H31 N O2'
_chemical_formula_weight         461.58
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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                   10.3110(4)
_cell_length_b                   11.2258(5)
_cell_length_c                   12.8508(5)
_cell_angle_alpha                91.396(3)
_cell_angle_beta                 99.313(3)
_cell_angle_gamma                117.296(4)
_cell_volume                     1296.15(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8092
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4860
_cell_measurement_theta_min      3.9930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17878
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.873
_diffrn_reflns_theta_min         3.569
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  84.00   1.00    9.10    --   15.20  57.00   0.00   90
  2  ω    -57.00  41.00   1.00    9.10    --   15.20 -38.00-150.00   98
  3  ω    -57.00  41.00   1.00    9.10    --   15.20 -38.00 120.00   98
  4  ω    -15.00  42.00   1.00    9.10    --   15.20  77.00 120.00   57
  5  ω    -39.00  52.00   1.00    9.10    --  -17.23  57.00  30.00   91
  6  ω    -41.00  14.00   1.00    9.10    --  -17.23 -80.00 170.00   55
  7  ω    -15.00  10.00   1.00    9.10    --   15.20 -99.00 120.00   25
  8  ω    -43.00  55.00   1.00    9.10    --  -17.23  38.00   0.00   98
  9  ω    -86.00   4.00   1.00    9.10    --  -17.23 -57.00-120.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0179633000
_diffrn_orient_matrix_UB_12      -0.0428196000
_diffrn_orient_matrix_UB_13      -0.0293547000
_diffrn_orient_matrix_UB_21      -0.0660792000
_diffrn_orient_matrix_UB_22      -0.0197531000
_diffrn_orient_matrix_UB_23      -0.0382884000
_diffrn_orient_matrix_UB_31      0.0392355000
_diffrn_orient_matrix_UB_32      0.0538190000
_diffrn_orient_matrix_UB_33      -0.0289959000
_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                4198
_reflns_number_total             5440
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5440
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.061
_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)+(0.0614P)²+0.5089P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1553
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C14(H14), C10(H10), C13(H13), C4(H4), C7(H7), C11(H11), C22(H22),
 C3(H3), C28(H28), C26(H26), C32(H32), C23(H23), C24(H24), C25(H25), C29(H29),
 C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C1(H1A,H1B,H1C)
;
_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
O2 O 0.32518(16) 0.71476(13) 0.46078(12) 0.0591(4) Uani 1 1 d . . . . .
N1 N 0.56167(15) 0.70747(13) 0.22688(11) 0.0397(3) Uani 1 1 d . . . . .
O1 O 0.53892(17) 0.85321(14) 0.41626(16) 0.0780(5) Uani 1 1 d . . . . .
C5 C 0.44010(18) 0.46268(16) 0.23217(13) 0.0374(4) Uani 1 1 d . . . . .
C9 C 0.29324(18) 0.59023(16) 0.21176(13) 0.0381(4) Uani 1 1 d . . . . .
C20 C 0.69922(19) 0.76078(16) 0.26843(13) 0.0389(4) Uani 1 1 d . . . . .
C16 C 0.44861(19) 0.61411(17) 0.38691(13) 0.0410(4) Uani 1 1 d . . . . .
H16A H 0.365325 0.537413 0.406157 0.049 Uiso 1 1 calc R U . . .
H16B H 0.539413 0.616286 0.424300 0.049 Uiso 1 1 calc R U . . .
C8 C 0.44067(18) 0.59482(16) 0.26569(13) 0.0367(4) Uani 1 1 d . . . . .
C21 C 0.77517(19) 0.72339(19) 0.36185(14) 0.0449(4) Uani 1 1 d . . . . .
C17 C 0.4454(2) 0.74075(18) 0.42176(14) 0.0454(4) Uani 1 1 d . . . . .
C6 C 0.4387(2) 0.43271(18) 0.12681(15) 0.0476(4) Uani 1 1 d . . . . .
H6 H 0.433905 0.491159 0.078087 0.057 Uiso 1 1 calc R U . . .
C27 C 0.8009(2) 0.87954(17) 0.21990(14) 0.0444(4) Uani 1 1 d . . . . .
C14 C 0.1589(2) 0.47921(19) 0.21696(15) 0.0487(4) Uani 1 1 d . . . . .
H14 H 0.159053 0.405751 0.248799 0.058 Uiso 1 1 calc R U . . .
C12 C 0.0186(2) 0.5817(2) 0.12652(15) 0.0506(5) Uani 1 1 d . . . . .
C10 C 0.2875(2) 0.69634(19) 0.16302(15) 0.0497(4) Uani 1 1 d . . . . .
H10 H 0.375570 0.772039 0.157940 0.060 Uiso 1 1 calc R U . . .
C13 C 0.0248(2) 0.4762(2) 0.17552(16) 0.0541(5) Uani 1 1 d . . . . .
H13 H -0.063481 0.400880 0.180882 0.065 Uiso 1 1 calc R U . . .
C4 C 0.4406(2) 0.37026(19) 0.30097(16) 0.0542(5) Uani 1 1 d . . . . .
H4 H 0.436553 0.384945 0.371636 0.065 Uiso 1 1 calc R U . . .
C2 C 0.4505(2) 0.22835(19) 0.16222(19) 0.0582(5) Uani 1 1 d . . . . .
C7 C 0.4443(2) 0.3183(2) 0.09240(17) 0.0575(5) Uani 1 1 d . . . . .
H7 H 0.443866 0.301195 0.021131 0.069 Uiso 1 1 calc R U . . .
C11 C 0.1518(2) 0.6916(2) 0.12137(17) 0.0561(5) Uani 1 1 d . . . . .
H11 H 0.151171 0.764700 0.089187 0.067 Uiso 1 1 calc R U . . .
C22 C 0.7891(2) 0.6069(2) 0.35554(19) 0.0569(5) Uani 1 1 d . . . . .
H22 H 0.749342 0.548862 0.292809 0.068 Uiso 1 1 calc R U . . .
C3 C 0.4471(3) 0.2556(2) 0.26564(19) 0.0635(6) Uani 1 1 d . . . . .
H3 H 0.449143 0.195669 0.313748 0.076 Uiso 1 1 calc R U . . .
C28 C 0.9449(2) 0.9063(2) 0.21810(19) 0.0617(5) Uani 1 1 d . . . . .
H28 H 0.980696 0.850028 0.248317 0.074 Uiso 1 1 calc R U . . .
C26 C 0.8385(2) 0.8102(3) 0.45520(16) 0.0631(6) Uani 1 1 d . . . . .
H26 H 0.833736 0.890842 0.459574 0.076 Uiso 1 1 calc R U . . .
C15 C -0.1281(2) 0.5748(3) 0.07790(18) 0.0670(6) Uani 1 1 d . . . . .
H15A H -0.148183 0.551009 0.002634 0.101 Uiso 1 1 calc R U . . .
H15B H -0.123841 0.661011 0.091910 0.101 Uiso 1 1 calc R U . . .
H15C H -0.205876 0.507807 0.108186 0.101 Uiso 1 1 calc R U . . .
C18 C 0.3075(3) 0.8293(2) 0.4952(2) 0.0658(6) Uani 1 1 d . . . . .
H18A H 0.404029 0.903384 0.526777 0.079 Uiso 1 1 calc R U . . .
H18B H 0.246039 0.805118 0.548740 0.079 Uiso 1 1 calc R U . . .
C32 C 0.7533(3) 0.9663(2) 0.1767(2) 0.0748(7) Uani 1 1 d . . . . .
H32 H 0.656582 0.950647 0.176918 0.090 Uiso 1 1 calc R U . . .
C23 C 0.8624(3) 0.5764(3) 0.4427(3) 0.0804(8) Uani 1 1 d . . . . .
H23 H 0.872001 0.498181 0.437886 0.096 Uiso 1 1 calc R U . . .
C24 C 0.9201(3) 0.6599(4) 0.5349(2) 0.0938(11) Uani 1 1 d . . . . .
H24 H 0.967375 0.637708 0.593263 0.113 Uiso 1 1 calc R U . . .
C25 C 0.9091(3) 0.7766(4) 0.54231(19) 0.0873(9) Uani 1 1 d . . . . .
H25 H 0.948834 0.833516 0.605645 0.105 Uiso 1 1 calc R U . . .
C29 C 1.0366(3) 1.0154(3) 0.1721(2) 0.0816(8) Uani 1 1 d . . . . .
H29 H 1.132668 1.030654 0.169896 0.098 Uiso 1 1 calc R U . . .
C30 C 0.9884(3) 1.1004(3) 0.1301(2) 0.0880(9) Uani 1 1 d . . . . .
H30 H 1.050957 1.174307 0.099540 0.106 Uiso 1 1 calc R U . . .
C19 C 0.2388(3) 0.8716(3) 0.4061(3) 0.0903(9) Uani 1 1 d . . . . .
H19A H 0.306183 0.907930 0.358101 0.135 Uiso 1 1 calc R U . . .
H19B H 0.215870 0.939519 0.431648 0.135 Uiso 1 1 calc R U . . .
H19C H 0.148866 0.795497 0.369832 0.135 Uiso 1 1 calc R U . . .
C1 C 0.4597(4) 0.1037(3) 0.1250(3) 0.0967(9) Uani 1 1 d . . . . .
H1A H 0.365497 0.039714 0.083046 0.145 Uiso 1 1 calc R U . . .
H1B H 0.484221 0.064054 0.185390 0.145 Uiso 1 1 calc R U . . .
H1C H 0.535223 0.128436 0.082844 0.145 Uiso 1 1 calc R U . . .
C31 C 0.8476(4) 1.0770(3) 0.1329(3) 0.0987(10) Uani 1 1 d . . . . .
H31 H 0.814394 1.136006 0.105023 0.118 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
O2 C17 1.323(2) . ?
O2 C18 1.447(2) . ?
N1 C20 1.271(2) . ?
N1 C8 1.480(2) . ?
O1 C17 1.199(2) . ?
C5 C8 1.532(2) . ?
C5 C6 1.383(2) . ?
C5 C4 1.381(2) . ?
C9 C8 1.542(2) . ?
C9 C14 1.388(2) . ?
C9 C10 1.380(2) . ?
C20 C21 1.501(2) . ?
C20 C27 1.495(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C8 1.551(2) . ?
C16 C17 1.497(2) . ?
C21 C22 1.381(3) . ?
C21 C26 1.386(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(3) . ?
C27 C28 1.378(3) . ?
C27 C32 1.369(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.384(3) . ?
C12 C13 1.378(3) . ?
C12 C11 1.376(3) . ?
C12 C15 1.506(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.391(3) . ?
C13 H13 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.388(3) . ?
C2 C7 1.383(3) . ?
C2 C3 1.366(3) . ?
C2 C1 1.516(3) . ?
C7 H7 0.9300 . ?
C11 H11 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.387(3) . ?
C3 H3 0.9300 . ?
C28 H28 0.9300 . ?
C28 C29 1.378(3) . ?
C26 H26 0.9300 . ?
C26 C25 1.390(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.453(4) . ?
C32 H32 0.9300 . ?
C32 C31 1.382(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.358(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.368(4) . ?
C25 H25 0.9300 . ?
C29 H29 0.9300 . ?
C29 C30 1.350(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.358(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C31 H31 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
C17 O2 C18 117.03(15) . . ?
C20 N1 C8 125.51(14) . . ?
C6 C5 C8 118.69(14) . . ?
C4 C5 C8 123.95(16) . . ?
C4 C5 C6 117.36(16) . . ?
C14 C9 C8 119.74(15) . . ?
C10 C9 C8 122.71(15) . . ?
C10 C9 C14 117.44(16) . . ?
N1 C20 C21 129.11(15) . . ?
N1 C20 C27 116.26(15) . . ?
C27 C20 C21 114.61(14) . . ?
H16A C16 H16B 107.8 . . ?
C8 C16 H16A 109.0 . . ?
C8 C16 H16B 109.0 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C17 C16 C8 112.78(14) . . ?
N1 C8 C5 108.91(13) . . ?
N1 C8 C9 106.99(12) . . ?
N1 C8 C16 113.78(13) . . ?
C5 C8 C9 109.34(13) . . ?
C5 C8 C16 111.50(13) . . ?
C9 C8 C16 106.12(13) . . ?
C22 C21 C20 121.43(18) . . ?
C22 C21 C26 119.04(19) . . ?
C26 C21 C20 119.47(18) . . ?
O2 C17 C16 111.73(15) . . ?
O1 C17 O2 122.87(18) . . ?
O1 C17 C16 125.39(17) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.52(18) . . ?
C7 C6 H6 119.2 . . ?
C28 C27 C20 121.56(17) . . ?
C32 C27 C20 120.51(17) . . ?
C32 C27 C28 117.92(19) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.03(18) . . ?
C13 C14 H14 119.5 . . ?
C13 C12 C15 121.1(2) . . ?
C11 C12 C13 117.19(17) . . ?
C11 C12 C15 121.6(2) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.89(18) . . ?
C11 C10 H10 119.6 . . ?
C14 C13 H13 119.1 . . ?
C12 C13 C14 121.70(18) . . ?
C12 C13 H13 119.1 . . ?
C5 C4 H4 119.7 . . ?
C5 C4 C3 120.61(19) . . ?
C3 C4 H4 119.7 . . ?
C7 C2 C1 121.1(2) . . ?
C3 C2 C7 117.50(18) . . ?
C3 C2 C1 121.4(2) . . ?
C6 C7 C2 121.02(19) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
C12 C11 C10 121.75(18) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0(2) . . ?
C23 C22 H22 120.0 . . ?
C4 C3 H3 119.0 . . ?
C2 C3 C4 121.90(19) . . ?
C2 C3 H3 119.0 . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.8(2) . . ?
C29 C28 H28 119.6 . . ?
C21 C26 H26 120.0 . . ?
C21 C26 C25 120.0(3) . . ?
C25 C26 H26 120.0 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 C19 110.6(2) . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C27 C32 H32 119.7 . . ?
C27 C32 C31 120.6(2) . . ?
C31 C32 H32 119.7 . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.5(3) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.3(2) . . ?
C25 C24 H24 119.9 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 C26 120.0(3) . . ?
C24 C25 H25 120.0 . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.7(2) . . ?
C30 C29 H29 119.7 . . ?
C29 C30 H30 120.3 . . ?
C29 C30 C31 119.3(2) . . ?
C31 C30 H30 120.3 . . ?
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 . . ?
C32 C31 H31 119.7 . . ?
C30 C31 C32 120.7(3) . . ?
C30 C31 H31 119.7 . . ?

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
N1 C20 C21 C22 71.7(3) . . . . ?
N1 C20 C21 C26 -111.1(2) . . . . ?
N1 C20 C27 C28 -148.29(19) . . . . ?
N1 C20 C27 C32 32.5(3) . . . . ?
C5 C6 C7 C2 0.4(3) . . . . ?
C5 C4 C3 C2 -1.2(3) . . . . ?
C9 C14 C13 C12 0.8(3) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C20 N1 C8 C5 -77.21(19) . . . . ?
C20 N1 C8 C9 164.70(15) . . . . ?
C20 N1 C8 C16 47.8(2) . . . . ?
C20 C21 C22 C23 178.79(18) . . . . ?
C20 C21 C26 C25 179.97(19) . . . . ?
C20 C27 C28 C29 179.3(2) . . . . ?
C20 C27 C32 C31 179.3(2) . . . . ?
C8 N1 C20 C21 2.3(3) . . . . ?
C8 N1 C20 C27 -176.17(14) . . . . ?
C8 C5 C6 C7 177.30(17) . . . . ?
C8 C5 C4 C3 -176.96(18) . . . . ?
C8 C9 C14 C13 175.65(16) . . . . ?
C8 C9 C10 C11 -175.77(17) . . . . ?
C8 C16 C17 O2 116.01(17) . . . . ?
C8 C16 C17 O1 -64.2(3) . . . . ?
C21 C20 C27 C28 33.0(2) . . . . ?
C21 C20 C27 C32 -146.2(2) . . . . ?
C21 C22 C23 C24 0.4(3) . . . . ?
C21 C26 C25 C24 2.0(3) . . . . ?
C17 O2 C18 C19 84.6(2) . . . . ?
C17 C16 C8 N1 57.83(19) . . . . ?
C17 C16 C8 C5 -178.52(13) . . . . ?
C17 C16 C8 C9 -59.54(17) . . . . ?
C6 C5 C8 N1 -51.4(2) . . . . ?
C6 C5 C8 C9 65.24(19) . . . . ?
C6 C5 C8 C16 -177.72(15) . . . . ?
C6 C5 C4 C3 3.2(3) . . . . ?
C27 C20 C21 C22 -109.76(19) . . . . ?
C27 C20 C21 C26 67.4(2) . . . . ?
C27 C28 C29 C30 1.7(4) . . . . ?
C27 C32 C31 C30 1.2(5) . . . . ?
C14 C9 C8 N1 167.59(15) . . . . ?
C14 C9 C8 C5 49.8(2) . . . . ?
C14 C9 C8 C16 -70.59(19) . . . . ?
C14 C9 C10 C11 0.3(3) . . . . ?
C10 C9 C8 N1 -16.4(2) . . . . ?
C10 C9 C8 C5 -134.22(17) . . . . ?
C10 C9 C8 C16 105.39(18) . . . . ?
C10 C9 C14 C13 -0.5(3) . . . . ?
C13 C12 C11 C10 0.4(3) . . . . ?
C4 C5 C8 N1 128.78(18) . . . . ?
C4 C5 C8 C9 -114.63(19) . . . . ?
C4 C5 C8 C16 2.4(2) . . . . ?
C4 C5 C6 C7 -2.8(3) . . . . ?
C7 C2 C3 C4 -1.3(3) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C22 C21 C26 C25 -2.8(3) . . . . ?
C22 C23 C24 C25 -1.2(4) . . . . ?
C3 C2 C7 C6 1.6(3) . . . . ?
C28 C27 C32 C31 0.0(4) . . . . ?
C28 C29 C30 C31 -0.5(5) . . . . ?
C26 C21 C22 C23 1.6(3) . . . . ?
C15 C12 C13 C14 177.54(18) . . . . ?
C15 C12 C11 C10 -177.77(19) . . . . ?
C18 O2 C17 O1 1.5(3) . . . . ?
C18 O2 C17 C16 -178.69(17) . . . . ?
C32 C27 C28 C29 -1.4(3) . . . . ?
C23 C24 C25 C26 0.0(4) . . . . ?
C29 C30 C31 C32 -1.0(5) . . . . ?
C1 C2 C7 C6 -178.8(2) . . . . ?
C1 C2 C3 C4 179.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.443
_oxdiff_exptl_absorpt_empirical_full_min 0.679
####################################################################### 
# 
# 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_20220108-xpj_auto
_database_code_depnum_ccdc_archive 'CCDC 2143809'
loop_
_audit_author_name
_audit_author_address
'Peng-Ju Xia'
;Guangxi normal university
China
;
_audit_update_record             
;
2022-01-22 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_audit_creation_date             2022-01-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 Cl N O2'
_chemical_formula_sum            'C24 H22 Cl N O2'
_chemical_formula_weight         391.87
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cl'
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'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2336(4)
_cell_length_b                   20.3550(6)
_cell_length_c                   22.5192(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4232.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5157
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4980
_cell_measurement_theta_min      3.8320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14734
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.900
_diffrn_reflns_theta_min         3.372
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  13.00   1.00   28.38    --  -17.23 -77.00  90.00   55
  2  ω    -93.00 -39.00   1.00   28.38    --  -17.23-178.00 -90.00   54
  3  ω    -58.00  26.00   1.00   28.38    --  -17.23 -19.00-180.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0524970000
_diffrn_orient_matrix_UB_12      -0.0157726000
_diffrn_orient_matrix_UB_13      0.0179730000
_diffrn_orient_matrix_UB_21      -0.0431375000
_diffrn_orient_matrix_UB_22      0.0061493000
_diffrn_orient_matrix_UB_23      0.0255040000
_diffrn_orient_matrix_UB_31      -0.0357803000
_diffrn_orient_matrix_UB_32      -0.0304922000
_diffrn_orient_matrix_UB_33      -0.0041862000
_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                3109
_reflns_number_total             4380
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.062
_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)+(0.0543P)²+1.4322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1408
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C11(H11), C8(H8), C23(H23), C10(H10), C7(H7), C18(H18), C14(H14),
 C15(H15), C22(H22), C20(H20), C16(H16), C17(H17), C21(H21)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.90710(9) 0.11289(4) 0.27746(3) 0.0891(3) Uani 1 1 d . . . . .
N1 N 0.57598(18) 0.09859(7) 0.54415(7) 0.0460(4) Uani 1 1 d . . . . .
C19 C 0.3793(2) 0.15382(9) 0.58928(8) 0.0424(4) Uani 1 1 d . . . . .
C13 C 0.6336(2) 0.20258(9) 0.59505(9) 0.0447(5) Uani 1 1 d . . . . .
C6 C 0.7698(2) 0.09416(8) 0.46896(9) 0.0435(5) Uani 1 1 d . . . . .
C12 C 0.5359(2) 0.14875(9) 0.57391(8) 0.0413(4) Uani 1 1 d . . . . .
O1 O 0.81055(19) 0.04082(9) 0.65128(7) 0.0722(5) Uani 1 1 d . . . . .
C24 C 0.2928(2) 0.09807(10) 0.58915(10) 0.0528(5) Uani 1 1 d . . . . .
H24 H 0.332920 0.057708 0.578951 0.063 Uiso 1 1 calc R U . . .
C5 C 0.7293(2) 0.08565(9) 0.53373(9) 0.0453(5) Uani 1 1 d . . . . .
H5 H 0.787909 0.115269 0.558208 0.054 Uiso 1 1 calc R U . . .
C11 C 0.6707(2) 0.08549(10) 0.42356(10) 0.0527(5) Uani 1 1 d . . . . .
H11 H 0.574865 0.075819 0.432727 0.063 Uiso 1 1 calc R U . . .
C3 C 0.7279(2) 0.00309(11) 0.61739(10) 0.0553(5) Uani 1 1 d . . . . .
C4 C 0.7564(3) 0.01415(10) 0.55288(9) 0.0540(5) Uani 1 1 d . . . . .
H4A H 0.694469 -0.014677 0.529811 0.065 Uiso 1 1 calc R U . . .
H4B H 0.856109 0.002652 0.544220 0.065 Uiso 1 1 calc R U . . .
C9 C 0.8544(3) 0.10515(10) 0.35144(9) 0.0540(5) Uani 1 1 d . . . . .
C8 C 0.9552(3) 0.11376(10) 0.39550(10) 0.0557(5) Uani 1 1 d . . . . .
H8 H 1.051096 0.123012 0.386093 0.067 Uiso 1 1 calc R U . . .
C23 C 0.1479(3) 0.10177(12) 0.60399(11) 0.0649(6) Uani 1 1 d . . . . .
H23 H 0.091632 0.063876 0.604272 0.078 Uiso 1 1 calc R U . . .
C10 C 0.7121(3) 0.09100(11) 0.36468(10) 0.0583(6) Uani 1 1 d . . . . .
H10 H 0.644723 0.085218 0.334442 0.070 Uiso 1 1 calc R U . . .
C7 C 0.9122(2) 0.10850(10) 0.45395(10) 0.0511(5) Uani 1 1 d . . . . .
H7 H 0.980071 0.114682 0.483962 0.061 Uiso 1 1 calc R U . . .
O2 O 0.6414(2) -0.03464(10) 0.63725(9) 0.0941(6) Uani 1 1 d . . . . .
C18 C 0.6498(3) 0.21503(11) 0.65500(10) 0.0591(6) Uani 1 1 d . . . . .
H18 H 0.598656 0.190042 0.682483 0.071 Uiso 1 1 calc R U . . .
C14 C 0.7091(2) 0.24126(10) 0.55528(10) 0.0550(5) Uani 1 1 d . . . . .
H14 H 0.699358 0.233835 0.514727 0.066 Uiso 1 1 calc R U . . .
C15 C 0.7991(3) 0.29089(11) 0.57516(13) 0.0669(7) Uani 1 1 d . . . . .
H15 H 0.848780 0.316904 0.547988 0.080 Uiso 1 1 calc R U . . .
C22 C 0.0868(3) 0.16085(13) 0.61825(12) 0.0679(7) Uani 1 1 d . . . . .
H22 H -0.011138 0.163254 0.627650 0.081 Uiso 1 1 calc R U . . .
C20 C 0.3157(2) 0.21295(10) 0.60449(11) 0.0599(6) Uani 1 1 d . . . . .
H20 H 0.371657 0.250919 0.605213 0.072 Uiso 1 1 calc R U . . .
C16 C 0.8153(3) 0.30180(12) 0.63480(14) 0.0715(7) Uani 1 1 d . . . . .
H16 H 0.876719 0.334854 0.648146 0.086 Uiso 1 1 calc R U . . .
C17 C 0.7412(3) 0.26423(13) 0.67454(12) 0.0725(7) Uani 1 1 d . . . . .
H17 H 0.752230 0.271705 0.715035 0.087 Uiso 1 1 calc R U . . .
C21 C 0.1702(3) 0.21658(13) 0.61866(12) 0.0715(7) Uani 1 1 d . . . . .
H21 H 0.128911 0.256815 0.628476 0.086 Uiso 1 1 calc R U . . .
C2 C 0.7971(4) 0.03288(18) 0.71525(12) 0.0991(10) Uani 1 1 d . . . . .
H2A H 0.696286 0.037079 0.726732 0.119 Uiso 1 1 calc R U . . .
H2B H 0.830119 -0.010575 0.726625 0.119 Uiso 1 1 calc R U . . .
C1 C 0.8813(5) 0.0815(2) 0.74517(15) 0.1349(15) Uani 1 1 d . . . . .
H1A H 0.980107 0.078814 0.732062 0.202 Uiso 1 1 calc R U . . .
H1B H 0.877077 0.074001 0.787221 0.202 Uiso 1 1 calc R U . . .
H1C H 0.843516 0.124310 0.736339 0.202 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
Cl1 C9 1.743(2) . ?
N1 C12 1.276(2) . ?
N1 C5 1.459(3) . ?
C19 C12 1.491(3) . ?
C19 C24 1.387(3) . ?
C19 C20 1.382(3) . ?
C13 C12 1.497(3) . ?
C13 C18 1.382(3) . ?
C13 C14 1.381(3) . ?
C6 C5 1.516(3) . ?
C6 C11 1.383(3) . ?
C6 C7 1.389(3) . ?
O1 C3 1.324(3) . ?
O1 C2 1.455(3) . ?
C24 H24 0.9300 . ?
C24 C23 1.381(3) . ?
C5 H5 0.9800 . ?
C5 C4 1.538(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.384(3) . ?
C3 C4 1.493(3) . ?
C3 O2 1.195(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C9 C8 1.372(3) . ?
C9 C10 1.378(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.379(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.367(3) . ?
C10 H10 0.9300 . ?
C7 H7 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.382(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.370(4) . ?
C22 H22 0.9300 . ?
C22 C21 1.371(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.361(4) . ?
C17 H17 0.9300 . ?
C21 H21 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.427(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
C12 N1 C5 120.67(16) . . ?
C24 C19 C12 120.08(17) . . ?
C20 C19 C12 122.00(17) . . ?
C20 C19 C24 117.92(19) . . ?
C18 C13 C12 120.68(18) . . ?
C14 C13 C12 121.00(18) . . ?
C14 C13 C18 118.32(19) . . ?
C11 C6 C5 122.23(19) . . ?
C11 C6 C7 118.25(19) . . ?
C7 C6 C5 119.46(18) . . ?
N1 C12 C19 117.28(17) . . ?
N1 C12 C13 125.32(17) . . ?
C19 C12 C13 117.40(16) . . ?
C3 O1 C2 117.2(2) . . ?
C19 C24 H24 119.6 . . ?
C23 C24 C19 120.8(2) . . ?
C23 C24 H24 119.6 . . ?
N1 C5 C6 111.94(16) . . ?
N1 C5 H5 109.5 . . ?
N1 C5 C4 106.48(16) . . ?
C6 C5 H5 109.5 . . ?
C6 C5 C4 109.74(15) . . ?
C4 C5 H5 109.5 . . ?
C6 C11 H11 119.5 . . ?
C6 C11 C10 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
O1 C3 C4 111.83(19) . . ?
O2 C3 O1 122.8(2) . . ?
O2 C3 C4 125.4(2) . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C3 C4 C5 112.75(16) . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C8 C9 Cl1 119.39(19) . . ?
C8 C9 C10 121.1(2) . . ?
C10 C9 Cl1 119.48(18) . . ?
C9 C8 H8 120.5 . . ?
C9 C8 C7 119.1(2) . . ?
C7 C8 H8 120.5 . . ?
C24 C23 H23 119.8 . . ?
C22 C23 C24 120.3(2) . . ?
C22 C23 H23 119.8 . . ?
C11 C10 H10 120.4 . . ?
C9 C10 C11 119.2(2) . . ?
C9 C10 H10 120.4 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7 119.3 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.7(2) . . ?
C17 C18 H18 119.7 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.7(2) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 120.0 . . ?
C23 C22 H22 120.1 . . ?
C23 C22 C21 119.9(2) . . ?
C21 C22 H22 120.1 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.1(2) . . ?
C21 C20 H20 119.5 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
C18 C17 H17 119.8 . . ?
C16 C17 C18 120.3(2) . . ?
C16 C17 H17 119.8 . . ?
C22 C21 C20 120.0(2) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
O1 C2 H2A 109.6 . . ?
O1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.2 . . ?
C1 C2 O1 110.1(3) . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
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 . . ?

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
Cl1 C9 C8 C7 179.07(15) . . . . ?
Cl1 C9 C10 C11 -179.43(16) . . . . ?
N1 C5 C4 C3 -62.4(2) . . . . ?
C19 C24 C23 C22 0.9(4) . . . . ?
C19 C20 C21 C22 0.5(4) . . . . ?
C13 C18 C17 C16 0.9(4) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C6 C5 C4 C3 176.25(18) . . . . ?
C6 C11 C10 C9 0.2(3) . . . . ?
C12 N1 C5 C6 -111.69(19) . . . . ?
C12 N1 C5 C4 128.39(19) . . . . ?
C12 C19 C24 C23 179.2(2) . . . . ?
C12 C19 C20 C21 -179.9(2) . . . . ?
C12 C13 C18 C17 179.3(2) . . . . ?
C12 C13 C14 C15 179.98(19) . . . . ?
O1 C3 C4 C5 -59.3(3) . . . . ?
C24 C19 C12 N1 20.9(3) . . . . ?
C24 C19 C12 C13 -158.61(18) . . . . ?
C24 C19 C20 C21 -0.5(3) . . . . ?
C24 C23 C22 C21 -0.9(4) . . . . ?
C5 N1 C12 C19 -172.24(16) . . . . ?
C5 N1 C12 C13 7.2(3) . . . . ?
C5 C6 C11 C10 -177.38(18) . . . . ?
C5 C6 C7 C8 177.08(17) . . . . ?
C11 C6 C5 N1 -27.0(2) . . . . ?
C11 C6 C5 C4 91.0(2) . . . . ?
C11 C6 C7 C8 -0.3(3) . . . . ?
C3 O1 C2 C1 -173.9(3) . . . . ?
C9 C8 C7 C6 0.6(3) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C23 C22 C21 C20 0.2(4) . . . . ?
C10 C9 C8 C7 -0.4(3) . . . . ?
C7 C6 C5 N1 155.73(17) . . . . ?
C7 C6 C5 C4 -86.3(2) . . . . ?
C7 C6 C11 C10 -0.1(3) . . . . ?
O2 C3 C4 C5 120.4(3) . . . . ?
C18 C13 C12 N1 -118.4(2) . . . . ?
C18 C13 C12 C19 61.1(2) . . . . ?
C18 C13 C14 C15 0.3(3) . . . . ?
C14 C13 C12 N1 62.0(3) . . . . ?
C14 C13 C12 C19 -118.6(2) . . . . ?
C14 C13 C18 C17 -1.1(3) . . . . ?
C14 C15 C16 C17 -0.8(4) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C20 C19 C12 N1 -159.7(2) . . . . ?
C20 C19 C12 C13 20.8(3) . . . . ?
C20 C19 C24 C23 -0.2(3) . . . . ?
C2 O1 C3 C4 -177.7(2) . . . . ?
C2 O1 C3 O2 2.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.813
_oxdiff_exptl_absorpt_empirical_full_min 0.674
