# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_xh-7-28
_database_code_depnum_ccdc_archive 'CCDC 2277737'
loop_
_audit_author_name
_audit_author_address
'Xu Hong'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-06-29 deposited with the CCDC.	2024-05-28 downloaded from the CCDC.
;
_audit_creation_date             2022-07-02
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H17 N O4'
_chemical_formula_sum            'C25 H17 N O4'
_chemical_formula_weight         395.39
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.62350(10)
_cell_length_b                   11.7760(2)
_cell_length_c                   16.9508(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1920.97(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5373
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      71.3830
_cell_measurement_theta_min      2.6330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82455
_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 black'
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0115
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6335
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.602
_diffrn_reflns_theta_min         4.572
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     80.00 132.00   0.50    0.50    --   42.30  77.00  90.00  104
  2  ω     21.00  73.00   0.50    0.50    --   42.30 -57.00-180.00  104
  3  ω     50.00 126.00   0.50    0.50    --   42.30  57.00 -90.00  152
  4  ω    -35.00  -9.00   0.50    0.50    --   42.30 -57.00-180.00   52
  5  ω    143.00 183.00   0.50    0.50    --  101.60  50.00 120.00   80
  6  ω    102.00 144.00   0.50    0.50    --  101.60 -82.00-180.00   84
  7  ω    161.00 189.00   0.50    0.50    --  101.60  82.00  30.00   56
  8  ω     70.00 191.00   0.50    0.50    --  101.60  50.00 150.00  242
  9  ω     21.00  85.00   0.50    0.50    --  101.60 -50.00  30.00  128
 10  ω     25.00 131.00   0.50    0.50    --  101.60 -77.00 -60.00  212
;
_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      -0.1459355000
_diffrn_orient_matrix_UB_12      -0.0211783000
_diffrn_orient_matrix_UB_13      -0.0342731000
_diffrn_orient_matrix_UB_21      0.0489318000
_diffrn_orient_matrix_UB_22      0.0449483000
_diffrn_orient_matrix_UB_23      -0.0805637000
_diffrn_orient_matrix_UB_31      0.0441494000
_diffrn_orient_matrix_UB_32      -0.1211499000
_diffrn_orient_matrix_UB_33      -0.0239818000
_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         0.619
_reflns_Friedel_fraction_full    0.853
_reflns_Friedel_fraction_max     0.813
_reflns_number_gt                3317
_reflns_number_total             3418
_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-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1245 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3418
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.029
_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)+(0.0578P)²+0.2127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0837
_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:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.53634(15) 0.27813(11) 0.63736(9) 0.0367(3) Uani 1 1 d . . . . .
O2 O 0.77407(15) 0.67176(12) 0.72643(10) 0.0408(4) Uani 1 1 d . . . . .
O3 O 0.21812(15) 0.50786(13) 0.69585(9) 0.0403(4) Uani 1 1 d . . . . .
O4 O 0.4701(2) 0.51358(16) 0.46325(9) 0.0582(5) Uani 1 1 d . . . . .
N1 N 0.31437(17) 0.71230(13) 0.56965(9) 0.0276(3) Uani 1 1 d . . . . .
C1 C 0.71964(18) 0.36820(16) 0.70690(10) 0.0245(4) Uani 1 1 d . . . . .
C2 C 0.7792(2) 0.26522(16) 0.72868(11) 0.0279(4) Uani 1 1 d . . . . .
H2 H 0.737051 0.197358 0.714023 0.034 Uiso 1 1 calc R U . . .
C3 C 0.9016(2) 0.26346(17) 0.77229(11) 0.0317(4) Uani 1 1 d . . . . .
H3 H 0.941556 0.194368 0.786112 0.038 Uiso 1 1 calc R U . . .
C4 C 0.96423(19) 0.36414(18) 0.79528(12) 0.0335(4) Uani 1 1 d . . . . .
H4 H 1.046136 0.362477 0.824381 0.040 Uiso 1 1 calc R U . . .
C5 C 0.9051(2) 0.46692(17) 0.77499(11) 0.0310(4) Uani 1 1 d . . . . .
H5 H 0.946803 0.534376 0.790915 0.037 Uiso 1 1 calc R U . . .
C6 C 0.78349(19) 0.46987(16) 0.73087(10) 0.0256(4) Uani 1 1 d . . . . .
C7 C 0.72112(19) 0.58127(16) 0.70971(11) 0.0267(4) Uani 1 1 d . . . . .
C8 C 0.58804(18) 0.57765(15) 0.66578(10) 0.0221(3) Uani 1 1 d . . . . .
C9 C 0.52822(17) 0.47760(15) 0.64248(10) 0.0228(3) Uani 1 1 d . . . . .
C10 C 0.58798(19) 0.36730(15) 0.65984(10) 0.0246(4) Uani 1 1 d . . . . .
C11 C 0.39247(18) 0.50174(14) 0.59630(10) 0.0235(4) Uani 1 1 d . . . . .
C12 C 0.39503(19) 0.62938(15) 0.59925(10) 0.0246(4) Uani 1 1 d . . . . .
C13 C 0.50680(18) 0.67231(15) 0.63979(10) 0.0230(3) Uani 1 1 d . . . . .
C14 C 0.49737(19) 0.79386(15) 0.63572(10) 0.0242(4) Uani 1 1 d . . . . .
C15 C 0.3763(2) 0.81570(15) 0.59075(10) 0.0267(4) Uani 1 1 d . . . . .
C16 C 0.3327(2) 0.92524(17) 0.57192(11) 0.0333(4) Uani 1 1 d . . . . .
H16 H 0.252978 0.938229 0.542296 0.040 Uiso 1 1 calc R U . . .
C17 C 0.4139(2) 1.01370(16) 0.59942(12) 0.0362(5) Uani 1 1 d . . . . .
H17 H 0.388252 1.087988 0.587816 0.043 Uiso 1 1 calc R U . . .
C18 C 0.5331(2) 0.99426(16) 0.64412(12) 0.0340(4) Uani 1 1 d . . . . .
H18 H 0.585082 1.055841 0.661742 0.041 Uiso 1 1 calc R U . . .
C19 C 0.5759(2) 0.88544(15) 0.66283(11) 0.0281(4) Uani 1 1 d . . . . .
H19 H 0.655415 0.873557 0.692889 0.034 Uiso 1 1 calc R U . . .
C20 C 0.4080(2) 0.45692(16) 0.51048(11) 0.0299(4) Uani 1 1 d . . . . .
C21 C 0.3449(2) 0.34437(18) 0.49059(12) 0.0385(5) Uani 1 1 d . . . . .
H21A H 0.407476 0.284476 0.507306 0.046 Uiso 1 1 calc R U . . .
H21B H 0.334337 0.338806 0.433811 0.046 Uiso 1 1 calc R U . . .
C22 C 0.2040(2) 0.3263(2) 0.52932(13) 0.0430(5) Uani 1 1 d . . . . .
H22A H 0.138291 0.380998 0.508392 0.052 Uiso 1 1 calc R U . . .
H22B H 0.170222 0.250878 0.516458 0.052 Uiso 1 1 calc R U . . .
C23 C 0.2116(2) 0.33893(17) 0.61824(13) 0.0369(5) Uani 1 1 d . . . . .
H23A H 0.119581 0.328525 0.640434 0.044 Uiso 1 1 calc R U . . .
H23B H 0.271422 0.280149 0.639555 0.044 Uiso 1 1 calc R U . . .
C24 C 0.26647(19) 0.45301(15) 0.64236(11) 0.0257(4) Uani 1 1 d . . . . .
C25 C 0.1906(3) 0.70088(18) 0.52169(14) 0.0448(6) Uani 1 1 d . . . . .
H25A H 0.210693 0.724278 0.468652 0.067 Uiso 1 1 calc R U . . .
H25B H 0.118101 0.747747 0.542976 0.067 Uiso 1 1 calc R U . . .
H25C H 0.160967 0.623035 0.521655 0.067 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 C10 1.223(2) . ?
O2 C7 1.215(2) . ?
O3 C24 1.207(2) . ?
O4 C20 1.201(3) . ?
N1 C12 1.345(2) . ?
N1 C15 1.402(2) . ?
N1 C25 1.448(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.406(3) . ?
C1 C10 1.497(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.391(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(3) . ?
C6 C7 1.486(3) . ?
C7 C8 1.482(2) . ?
C8 C9 1.369(2) . ?
C8 C13 1.431(2) . ?
C9 C10 1.451(2) . ?
C9 C11 1.549(2) . ?
C11 C12 1.504(2) . ?
C11 C20 1.555(2) . ?
C11 C24 1.552(2) . ?
C12 C13 1.373(2) . ?
C13 C14 1.436(2) . ?
C14 C15 1.416(3) . ?
C14 C19 1.395(2) . ?
C15 C16 1.393(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.394(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.497(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.521(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.517(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.500(2) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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 C15 106.87(15) . . ?
C12 N1 C25 128.08(16) . . ?
C15 N1 C25 124.99(16) . . ?
C2 C1 C6 119.05(16) . . ?
C2 C1 C10 118.94(16) . . ?
C6 C1 C10 122.00(16) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.20(17) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.34(18) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.02(17) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.21(18) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 120.35(15) . . ?
C5 C6 C1 120.17(17) . . ?
C5 C6 C7 119.48(16) . . ?
O2 C7 C6 123.26(16) . . ?
O2 C7 C8 120.33(17) . . ?
C8 C7 C6 116.41(15) . . ?
C9 C8 C7 122.20(16) . . ?
C9 C8 C13 110.59(15) . . ?
C13 C8 C7 127.18(16) . . ?
C8 C9 C10 123.03(15) . . ?
C8 C9 C11 110.02(14) . . ?
C10 C9 C11 126.95(15) . . ?
O1 C10 C1 121.07(16) . . ?
O1 C10 C9 122.99(16) . . ?
C9 C10 C1 115.93(15) . . ?
C9 C11 C20 109.22(14) . . ?
C9 C11 C24 109.68(13) . . ?
C12 C11 C9 98.79(13) . . ?
C12 C11 C20 111.64(14) . . ?
C12 C11 C24 111.44(15) . . ?
C24 C11 C20 114.86(14) . . ?
N1 C12 C11 134.74(17) . . ?
N1 C12 C13 111.82(16) . . ?
C13 C12 C11 113.42(16) . . ?
C8 C13 C14 145.68(17) . . ?
C12 C13 C8 107.17(15) . . ?
C12 C13 C14 107.07(16) . . ?
C15 C14 C13 105.01(15) . . ?
C19 C14 C13 136.11(18) . . ?
C19 C14 C15 118.87(17) . . ?
N1 C15 C14 109.23(15) . . ?
C16 C15 N1 128.16(17) . . ?
C16 C15 C14 122.61(17) . . ?
C15 C16 H16 121.6 . . ?
C17 C16 C15 116.77(19) . . ?
C17 C16 H16 121.6 . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.63(18) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.45(18) . . ?
C19 C18 H18 119.3 . . ?
C14 C19 H19 120.7 . . ?
C18 C19 C14 118.68(18) . . ?
C18 C19 H19 120.7 . . ?
O4 C20 C11 118.88(17) . . ?
O4 C20 C21 122.94(18) . . ?
C21 C20 C11 118.18(16) . . ?
C20 C21 H21A 109.0 . . ?
C20 C21 H21B 109.0 . . ?
C20 C21 C22 112.90(18) . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
C21 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
C23 C22 C21 111.83(18) . . ?
C23 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C22 C23 H23A 109.2 . . ?
C22 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 C22 112.09(17) . . ?
C24 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
O3 C24 C11 118.77(16) . . ?
O3 C24 C23 123.27(18) . . ?
C23 C24 C11 117.96(16) . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
O2 C7 C8 C9 176.82(18) . . . . ?
O2 C7 C8 C13 -1.2(3) . . . . ?
O4 C20 C21 C22 -140.5(2) . . . . ?
N1 C12 C13 C8 -177.70(14) . . . . ?
N1 C12 C13 C14 -0.2(2) . . . . ?
N1 C15 C16 C17 -179.23(18) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C1 C6 C7 O2 -177.40(19) . . . . ?
C1 C6 C7 C8 2.4(2) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C1 C6 C7 -178.96(17) . . . . ?
C2 C1 C10 O1 -3.5(3) . . . . ?
C2 C1 C10 C9 177.15(16) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 179.87(17) . . . . ?
C5 C6 C7 O2 3.0(3) . . . . ?
C5 C6 C7 C8 -177.25(15) . . . . ?
C6 C1 C2 C3 -1.2(3) . . . . ?
C6 C1 C10 O1 177.63(17) . . . . ?
C6 C1 C10 C9 -1.7(2) . . . . ?
C6 C7 C8 C9 -2.9(2) . . . . ?
C6 C7 C8 C13 179.03(16) . . . . ?
C7 C8 C9 C10 1.2(3) . . . . ?
C7 C8 C9 C11 -178.63(15) . . . . ?
C7 C8 C13 C12 177.88(16) . . . . ?
C7 C8 C13 C14 2.1(4) . . . . ?
C8 C9 C10 O1 -178.15(18) . . . . ?
C8 C9 C10 C1 1.2(2) . . . . ?
C8 C9 C11 C12 0.75(17) . . . . ?
C8 C9 C11 C20 117.44(16) . . . . ?
C8 C9 C11 C24 -115.87(15) . . . . ?
C8 C13 C14 C15 175.4(2) . . . . ?
C8 C13 C14 C19 -3.3(4) . . . . ?
C9 C8 C13 C12 -0.33(19) . . . . ?
C9 C8 C13 C14 -176.2(2) . . . . ?
C9 C11 C12 N1 177.15(19) . . . . ?
C9 C11 C12 C13 -0.99(19) . . . . ?
C9 C11 C20 O4 -80.3(2) . . . . ?
C9 C11 C20 C21 99.6(2) . . . . ?
C9 C11 C24 O3 81.8(2) . . . . ?
C9 C11 C24 C23 -97.75(18) . . . . ?
C10 C1 C2 C3 179.91(16) . . . . ?
C10 C1 C6 C5 179.52(16) . . . . ?
C10 C1 C6 C7 -0.1(3) . . . . ?
C10 C9 C11 C12 -179.03(16) . . . . ?
C10 C9 C11 C20 -62.3(2) . . . . ?
C10 C9 C11 C24 64.3(2) . . . . ?
C11 C9 C10 O1 1.6(3) . . . . ?
C11 C9 C10 C1 -179.05(15) . . . . ?
C11 C12 C13 C8 0.9(2) . . . . ?
C11 C12 C13 C14 178.42(15) . . . . ?
C11 C20 C21 C22 39.6(3) . . . . ?
C12 N1 C15 C14 -0.94(19) . . . . ?
C12 N1 C15 C16 178.33(19) . . . . ?
C12 C11 C20 O4 27.9(3) . . . . ?
C12 C11 C20 C21 -152.22(17) . . . . ?
C12 C11 C24 O3 -26.6(2) . . . . ?
C12 C11 C24 C23 153.90(16) . . . . ?
C12 C13 C14 C15 -0.42(19) . . . . ?
C12 C13 C14 C19 -179.10(19) . . . . ?
C13 C8 C9 C10 179.48(16) . . . . ?
C13 C8 C9 C11 -0.31(19) . . . . ?
C13 C14 C15 N1 0.83(19) . . . . ?
C13 C14 C15 C16 -178.49(18) . . . . ?
C13 C14 C19 C18 178.0(2) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 N1 C12 C11 -177.48(19) . . . . ?
C15 N1 C12 C13 0.7(2) . . . . ?
C15 C14 C19 C18 -0.6(2) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 C14 0.3(3) . . . . ?
C19 C14 C15 N1 179.79(15) . . . . ?
C19 C14 C15 C16 0.5(3) . . . . ?
C20 C11 C12 N1 62.3(3) . . . . ?
C20 C11 C12 C13 -115.81(17) . . . . ?
C20 C11 C24 O3 -154.81(17) . . . . ?
C20 C11 C24 C23 25.7(2) . . . . ?
C20 C21 C22 C23 -56.2(3) . . . . ?
C21 C22 C23 C24 57.6(3) . . . . ?
C22 C23 C24 O3 137.9(2) . . . . ?
C22 C23 C24 C11 -42.6(2) . . . . ?
C24 C11 C12 N1 -67.6(3) . . . . ?
C24 C11 C12 C13 114.27(17) . . . . ?
C24 C11 C20 O4 156.03(19) . . . . ?
C24 C11 C20 C21 -24.1(2) . . . . ?
C25 N1 C12 C11 -0.3(3) . . . . ?
C25 N1 C12 C13 177.88(19) . . . . ?
C25 N1 C15 C14 -178.25(18) . . . . ?
C25 N1 C15 C16 1.0(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 1.632
_oxdiff_exptl_absorpt_empirical_full_min 0.699
####################################################################### 
# 
# 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_1419-xh-6_2
_database_code_depnum_ccdc_archive 'CCDC 2278494'
loop_
_audit_author_name
_audit_author_address
'Xu Hong'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-07-02 deposited with the CCDC.	2024-05-28 downloaded from the CCDC.
;
_audit_creation_date             2023-06-30
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H18 Cl N O4'
_chemical_formula_sum            'C25 H18 Cl N O4'
_chemical_formula_weight         431.85
_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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.1321(6)
_cell_length_b                   7.0726(2)
_cell_length_c                   21.8672(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.900(2)
_cell_angle_gamma                90
_cell_volume                     3992.88(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    99.98(18)
_cell_measurement_theta_max      77.1200
_cell_measurement_theta_min      3.6520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.981
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13198
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.355
_diffrn_reflns_theta_min         4.093
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(18)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00 -80.00   0.50    0.10    -- -104.00 125.00  90.00   52
  2  ω    -74.00 -40.00   0.50    0.10    -- -104.00 125.00  90.00   68
  3  ω    -77.00 -51.00   0.50    0.10    -- -104.00 125.00  60.00   52
  4  ω   -106.00 -80.00   0.50    0.10    -- -104.00 125.00  60.00   52
  5  ω    -59.00 -34.00   0.50    0.10    -- -104.00  57.00  90.00   50
  6  ω    -62.00 -33.00   0.50    0.10    -- -104.00  57.00 -60.00   58
  7  ω    -64.00 -37.00   0.50    0.10    -- -104.00  57.00-120.00   54
  8  ω    -64.00 -35.00   0.50    0.10    -- -104.00  57.00 -90.00   58
  9  ω   -120.00 -44.00   0.50    0.10    --  -48.03 -20.00 160.00  152
 10  ω   -134.00-108.00   0.50    0.10    -- -104.00 -20.00 160.00   52
 11  ω     35.00  60.00   0.50    0.10    --  106.53 -57.00-120.00   50
 12  ω     38.00  64.00   0.50    0.10    --  106.53 -57.00 -30.00   52
 13  ω     35.00  67.00   0.50    0.10    --  106.53 -57.00  30.00   64
 14  ω     37.00  65.00   0.50    0.10    --  106.53 -57.00   0.00   56
 15  ω     36.00  68.00   0.50    0.10    --  106.53 -57.00  60.00   64
 16  ω     34.00  60.00   0.50    0.10    --  106.53 -57.00  90.00   52
 17  ω     37.00  65.00   0.50    0.10    --  106.53 -57.00 120.00   56
 18  ω      2.00  28.00   0.50    0.10    --   48.03 -20.00 160.00   52
 19  ω     73.00 107.00   0.50    0.10    --  106.53-125.00  60.00   68
 20  ω     59.00 109.00   0.50    0.10    --  106.53-125.00-150.00  100
 21  ω    -25.00  25.00   0.50    0.10    --  -48.03  20.00 -32.00  100
 22  ω    -41.00  24.00   0.50    0.10    --  -48.03  38.00  90.00  130
 23  ω    -23.00   6.00   0.50    0.10    --  -48.03  19.00 120.00   58
 24  ω     51.00 122.00   0.50    0.10    --   48.03  20.00 -32.00  142
 25  ω     96.00 178.00   0.50    0.10    --  106.53  20.00 -32.00  164
 26  ω     39.00 140.00   0.50    0.10    --  106.53   0.00 -60.00  202
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0531741000
_diffrn_orient_matrix_UB_12      0.0244861000
_diffrn_orient_matrix_UB_13      -0.0408666000
_diffrn_orient_matrix_UB_21      -0.0243128000
_diffrn_orient_matrix_UB_22      0.0507169000
_diffrn_orient_matrix_UB_23      0.0577216000
_diffrn_orient_matrix_UB_31      0.0120308000
_diffrn_orient_matrix_UB_32      0.2103262000
_diffrn_orient_matrix_UB_33      -0.0091567000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3575
_reflns_number_total             4049
_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 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4049
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0603
_refine_ls_restrained_S_all      1.156
_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)+(0.1367P)²+0.4368P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1914
_refine_ls_wR_factor_ref         0.1953
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 0.44562(2) 0.92778(9) 0.67265(2) 0.0320(2) Uani 1 1 d . . . . .
O1 O 0.64649(5) 0.4491(2) 0.46600(6) 0.0279(4) Uani 1 1 d . . . . .
O2 O 0.78278(5) 0.4967(2) 0.67447(6) 0.0227(4) Uani 1 1 d . . . . .
O3 O 0.70853(5) 0.7740(2) 0.71727(6) 0.0237(3) Uani 1 1 d . . . . .
H3 H 0.711642 0.848501 0.747540 0.036 Uiso 1 1 calc R U . . .
O4 O 0.65044(6) 0.1585(2) 0.67082(6) 0.0299(4) Uani 1 1 d . . . . .
N1 N 0.52095(6) 0.3699(3) 0.56003(7) 0.0232(4) Uani 1 1 d . . . . .
C1 C 0.57407(7) 0.5994(3) 0.60594(8) 0.0202(4) Uani 1 1 d . . . . .
C2 C 0.58478(7) 0.7708(3) 0.63648(8) 0.0214(4) Uani 1 1 d . . . . .
H2 H 0.619150 0.818712 0.643691 0.026 Uiso 1 1 calc R U . . .
C3 C 0.54482(7) 0.8708(3) 0.65623(8) 0.0239(5) Uani 1 1 d . . . . .
H3A H 0.551518 0.988624 0.676767 0.029 Uiso 1 1 calc R U . . .
C4 C 0.49436(7) 0.7971(3) 0.64577(8) 0.0236(5) Uani 1 1 d . . . . .
C5 C 0.48125(7) 0.6305(3) 0.61485(8) 0.0244(5) Uani 1 1 d . . . . .
H5 H 0.446609 0.585280 0.607434 0.029 Uiso 1 1 calc R U . . .
C6 C 0.52221(7) 0.5313(3) 0.59493(8) 0.0218(4) Uani 1 1 d . . . . .
C7 C 0.57021(7) 0.3335(3) 0.54814(8) 0.0229(4) Uani 1 1 d . . . . .
H7 H 0.579369 0.230589 0.524104 0.028 Uiso 1 1 calc R U . . .
C8 C 0.60421(7) 0.4670(3) 0.57593(8) 0.0198(4) Uani 1 1 d . . . . .
C9 C 0.65999(7) 0.4749(3) 0.57527(8) 0.0187(4) Uani 1 1 d . . . . .
C10 C 0.67772(7) 0.4690(3) 0.51327(8) 0.0200(4) Uani 1 1 d . . . . .
C11 C 0.73383(7) 0.4937(3) 0.51090(8) 0.0195(4) Uani 1 1 d . . . . .
C12 C 0.75129(7) 0.4943(3) 0.45401(8) 0.0230(4) Uani 1 1 d . . . . .
H12 H 0.727324 0.477251 0.417079 0.028 Uiso 1 1 calc R U . . .
C13 C 0.80363(8) 0.5197(3) 0.45071(9) 0.0253(5) Uani 1 1 d . . . . .
H13 H 0.815449 0.520451 0.411747 0.030 Uiso 1 1 calc R U . . .
C14 C 0.83855(8) 0.5442(3) 0.50523(10) 0.0261(5) Uani 1 1 d . . . . .
H14 H 0.874203 0.563994 0.503209 0.031 Uiso 1 1 calc R U . . .
C15 C 0.82172(7) 0.5399(3) 0.56237(9) 0.0236(5) Uani 1 1 d . . . . .
H15 H 0.845888 0.554313 0.599265 0.028 Uiso 1 1 calc R U . . .
C16 C 0.76923(7) 0.5143(3) 0.56556(8) 0.0195(4) Uani 1 1 d . . . . .
C17 C 0.75117(7) 0.5020(3) 0.62651(8) 0.0196(4) Uani 1 1 d . . . . .
C18 C 0.69487(7) 0.4880(3) 0.62849(8) 0.0179(4) Uani 1 1 d . . . . .
C19 C 0.67807(7) 0.4729(3) 0.69002(8) 0.0194(4) Uani 1 1 d . . . . .
C20 C 0.68541(7) 0.6147(3) 0.73175(8) 0.0201(4) Uani 1 1 d . . . . .
C21 C 0.66576(8) 0.6087(3) 0.79289(8) 0.0275(5) Uani 1 1 d . . . . .
H21A H 0.633447 0.683580 0.789683 0.033 Uiso 1 1 calc R U . . .
H21B H 0.691694 0.668092 0.824939 0.033 Uiso 1 1 calc R U . . .
C22 C 0.65514(9) 0.4087(4) 0.81291(9) 0.0312(5) Uani 1 1 d . . . . .
H22A H 0.688389 0.343463 0.827002 0.037 Uiso 1 1 calc R U . . .
H22B H 0.635468 0.413374 0.848104 0.037 Uiso 1 1 calc R U . . .
C23 C 0.62451(8) 0.2988(4) 0.76012(9) 0.0299(5) Uani 1 1 d . . . . .
H23A H 0.589771 0.356345 0.749086 0.036 Uiso 1 1 calc R U . . .
H23B H 0.619840 0.167102 0.773577 0.036 Uiso 1 1 calc R U . . .
C24 C 0.65175(7) 0.2975(3) 0.70353(8) 0.0224(4) Uani 1 1 d . . . . .
C25 C 0.47588(7) 0.2512(3) 0.54163(9) 0.0284(5) Uani 1 1 d . . . . .
H25A H 0.470555 0.169403 0.576266 0.043 Uiso 1 1 calc R U . . .
H25B H 0.481389 0.173033 0.506221 0.043 Uiso 1 1 calc R U . . .
H25C H 0.445282 0.331060 0.529978 0.043 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 C4 1.7475(19) . ?
O1 C10 1.222(2) . ?
O2 C17 1.231(2) . ?
O3 H3 0.8400 . ?
O3 C20 1.340(2) . ?
O4 C24 1.213(3) . ?
N1 C6 1.371(3) . ?
N1 C7 1.376(2) . ?
N1 C25 1.451(2) . ?
C1 C2 1.391(3) . ?
C1 C6 1.423(3) . ?
C1 C8 1.445(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.403(3) . ?
C4 C5 1.375(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.372(3) . ?
C8 C9 1.461(3) . ?
C9 C10 1.500(2) . ?
C9 C18 1.366(2) . ?
C10 C11 1.486(2) . ?
C11 C12 1.390(2) . ?
C11 C16 1.401(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.393(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.396(3) . ?
C16 C17 1.484(2) . ?
C17 C18 1.482(2) . ?
C18 C19 1.482(2) . ?
C19 C20 1.349(3) . ?
C19 C24 1.470(3) . ?
C20 C21 1.505(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.519(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.514(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.520(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O3 H3 109.5 . . ?
C6 N1 C7 108.56(16) . . ?
C6 N1 C25 125.77(16) . . ?
C7 N1 C25 125.59(19) . . ?
C2 C1 C6 119.45(17) . . ?
C2 C1 C8 134.36(17) . . ?
C6 C1 C8 106.00(17) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.29(17) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3A 120.2 . . ?
C2 C3 C4 119.6(2) . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 Cl1 117.66(17) . . ?
C5 C4 Cl1 118.64(14) . . ?
C5 C4 C3 123.69(18) . . ?
C4 C5 H5 122.1 . . ?
C4 C5 C6 115.89(17) . . ?
C6 C5 H5 122.1 . . ?
N1 C6 C1 108.43(16) . . ?
N1 C6 C5 129.42(17) . . ?
C5 C6 C1 122.01(19) . . ?
N1 C7 H7 124.8 . . ?
C8 C7 N1 110.38(19) . . ?
C8 C7 H7 124.8 . . ?
C1 C8 C9 126.47(18) . . ?
C7 C8 C1 106.60(17) . . ?
C7 C8 C9 126.92(19) . . ?
C8 C9 C10 117.14(15) . . ?
C18 C9 C8 121.97(16) . . ?
C18 C9 C10 120.89(16) . . ?
O1 C10 C9 120.57(16) . . ?
O1 C10 C11 121.18(16) . . ?
C11 C10 C9 118.22(15) . . ?
C12 C11 C10 119.61(16) . . ?
C12 C11 C16 119.90(16) . . ?
C16 C11 C10 120.49(15) . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.53(17) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.29(16) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.68(17) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.90(18) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C17 120.04(16) . . ?
C15 C16 C11 119.67(16) . . ?
C15 C16 C17 120.26(16) . . ?
O2 C17 C16 120.16(16) . . ?
O2 C17 C18 120.76(15) . . ?
C18 C17 C16 119.02(15) . . ?
C9 C18 C17 120.96(15) . . ?
C9 C18 C19 121.08(15) . . ?
C17 C18 C19 117.78(15) . . ?
C20 C19 C18 121.95(18) . . ?
C20 C19 C24 120.86(16) . . ?
C24 C19 C18 117.18(17) . . ?
O3 C20 C19 119.17(16) . . ?
O3 C20 C21 117.52(17) . . ?
C19 C20 C21 123.19(19) . . ?
C20 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
C20 C21 C22 112.64(18) . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 108.0 . . ?
C23 C22 C21 110.92(18) . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C22 C23 H23A 109.3 . . ?
C22 C23 H23B 109.3 . . ?
C22 C23 C24 111.40(16) . . ?
H23A C23 H23B 108.0 . . ?
C24 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
O4 C24 C19 122.45(16) . . ?
O4 C24 C23 120.71(18) . . ?
C19 C24 C23 116.82(17) . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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 C4 C5 C6 -179.44(14) . . . . ?
O1 C10 C11 C12 0.0(3) . . . . ?
O1 C10 C11 C16 -179.3(2) . . . . ?
O2 C17 C18 C9 -173.4(2) . . . . ?
O2 C17 C18 C19 1.6(3) . . . . ?
O3 C20 C21 C22 -163.04(17) . . . . ?
N1 C7 C8 C1 -1.7(2) . . . . ?
N1 C7 C8 C9 178.56(18) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C1 C8 C9 C10 -126.3(2) . . . . ?
C1 C8 C9 C18 53.4(3) . . . . ?
C2 C1 C6 N1 175.06(16) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C2 C1 C8 C7 -173.4(2) . . . . ?
C2 C1 C8 C9 6.4(4) . . . . ?
C2 C3 C4 Cl1 179.13(14) . . . . ?
C2 C3 C4 C5 -2.0(3) . . . . ?
C3 C4 C5 C6 1.7(3) . . . . ?
C4 C5 C6 N1 -175.35(19) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C6 N1 C7 C8 1.3(2) . . . . ?
C6 C1 C2 C3 0.8(3) . . . . ?
C6 C1 C8 C7 1.4(2) . . . . ?
C6 C1 C8 C9 -178.83(18) . . . . ?
C7 N1 C6 C1 -0.4(2) . . . . ?
C7 N1 C6 C5 175.4(2) . . . . ?
C7 C8 C9 C10 53.4(3) . . . . ?
C7 C8 C9 C18 -126.9(2) . . . . ?
C8 C1 C2 C3 175.0(2) . . . . ?
C8 C1 C6 N1 -0.6(2) . . . . ?
C8 C1 C6 C5 -176.73(18) . . . . ?
C8 C9 C10 O1 -3.4(3) . . . . ?
C8 C9 C10 C11 174.75(18) . . . . ?
C8 C9 C18 C17 -178.0(2) . . . . ?
C8 C9 C18 C19 7.0(3) . . . . ?
C9 C10 C11 C12 -178.15(19) . . . . ?
C9 C10 C11 C16 2.5(3) . . . . ?
C9 C18 C19 C20 -119.7(2) . . . . ?
C9 C18 C19 C24 58.9(3) . . . . ?
C10 C9 C18 C17 1.7(3) . . . . ?
C10 C9 C18 C19 -173.24(19) . . . . ?
C10 C11 C12 C13 179.2(2) . . . . ?
C10 C11 C16 C15 -179.15(19) . . . . ?
C10 C11 C16 C17 3.0(3) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C11 C16 C17 O2 171.1(2) . . . . ?
C11 C16 C17 C18 -6.4(3) . . . . ?
C12 C11 C16 C15 1.5(3) . . . . ?
C12 C11 C16 C17 -176.29(19) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
C14 C15 C16 C17 177.6(2) . . . . ?
C15 C16 C17 O2 -6.7(3) . . . . ?
C15 C16 C17 C18 175.84(19) . . . . ?
C16 C11 C12 C13 -1.5(3) . . . . ?
C16 C17 C18 C9 4.0(3) . . . . ?
C16 C17 C18 C19 179.05(18) . . . . ?
C17 C18 C19 C20 65.2(3) . . . . ?
C17 C18 C19 C24 -116.1(2) . . . . ?
C18 C9 C10 O1 176.9(2) . . . . ?
C18 C9 C10 C11 -5.0(3) . . . . ?
C18 C19 C20 O3 0.0(3) . . . . ?
C18 C19 C20 C21 175.92(17) . . . . ?
C18 C19 C24 O4 11.2(3) . . . . ?
C18 C19 C24 C23 -167.20(16) . . . . ?
C19 C20 C21 C22 21.0(3) . . . . ?
C20 C19 C24 O4 -170.17(18) . . . . ?
C20 C19 C24 C23 11.4(3) . . . . ?
C20 C21 C22 C23 -47.0(2) . . . . ?
C21 C22 C23 C24 55.8(2) . . . . ?
C22 C23 C24 O4 143.4(2) . . . . ?
C22 C23 C24 C19 -38.2(3) . . . . ?
C24 C19 C20 O3 -178.54(16) . . . . ?
C24 C19 C20 C21 -2.7(3) . . . . ?
C25 N1 C6 C1 176.47(17) . . . . ?
C25 N1 C6 C5 -7.8(3) . . . . ?
C25 N1 C7 C8 -175.55(17) . . . . ?

_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 4.598
_oxdiff_exptl_absorpt_empirical_full_min 0.229
####################################################################### 
# 
# 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_xh-7-2-1
_database_code_depnum_ccdc_archive 'CCDC 2277739'
loop_
_audit_author_name
_audit_author_address
'Xu Hong'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2023-06-29 deposited with the CCDC.	2024-05-28 downloaded from the CCDC.
;
_audit_creation_date             2023-04-10
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H2 Cl2, 2(C27 H21 N O4)'
_chemical_formula_sum            'C55 H44 Cl2 N2 O8'
_chemical_formula_weight         931.82
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.9040(3)
_cell_length_b                   19.5240(5)
_cell_length_c                   18.0622(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.725(3)
_cell_angle_gamma                90
_cell_volume                     4497.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12703
_cell_measurement_temperature    295.25(10)
_cell_measurement_theta_max      76.0590
_cell_measurement_theta_min      3.3130
_shelx_estimated_absorpt_T_max   0.813
_shelx_estimated_absorpt_T_min   0.738
_exptl_absorpt_coefficient_mu    1.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1944
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            31882
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.354
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.25(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -32.00   0.50    1.50    --  -47.95 -60.00-136.00  170
  2  ω    -62.00  24.00   0.50    1.50    --  -47.95  60.00   2.00  172
  3  ω     -3.00  23.00   0.50    1.50    --   47.95 -60.00-136.00   52
  4  ω     24.00  52.00   0.50    1.50    --   47.95 -60.00-136.00   56
  5  ω    -44.00 -15.00   0.50    4.00    --  -86.25  60.00   2.00   58
  6  ω   -138.00-113.00   0.50    4.00    --  -86.25 -60.00-136.00   50
  7  ω     36.00  70.00   0.50    4.00    --  107.75 -60.00-136.00   68
  8  ω     92.00 178.00   0.50    4.00    --  107.75  60.00   2.00  172
  9  ω   -111.00 -85.00   0.50    1.50    --  -47.95-125.00 -30.00   52
 10  ω   -119.00 -73.00   0.50    1.50    --  -47.95-125.00-180.00   92
 11  ω   -106.00 -74.00   0.50    1.50    --  -47.95-125.00   0.00   64
 12  ω     52.00  77.00   0.50    1.50    --   47.95  60.00   2.00   50
 13  ω    -41.00 -13.00   0.50    4.00    --  -86.25  37.00 120.00   56
 14  ω    -39.00 -13.00   0.50    4.00    --  -86.25  37.00-180.00   52
 15  ω    -49.00 -16.00   0.50    4.00    --  -86.25  57.00 -60.00   66
 16  ω    -42.00 -17.00   0.50    4.00    --  -86.25  37.00-150.00   50
 17  ω    -39.00 -14.00   0.50    4.00    --  -86.25  37.00 -30.00   50
 18  ω    100.00 173.00   0.50    4.00    --  107.75  37.00 -60.00  146
 19  ω    136.00 178.00   0.50    4.00    --  107.75 125.00-180.00   84
 20  ω     36.00 106.00   0.50    4.00    --  107.75 -99.00-180.00  140
 21  ω     39.00  64.00   0.50    4.00    --  107.75 -57.00   0.00   50
 22  ω     36.00  61.00   0.50    4.00    --  107.75 -57.00 -60.00   50
 23  ω     96.00 122.00   0.50    4.00    --  107.75 125.00-180.00   52
 24  ω     55.00 102.00   0.50    4.00    --  107.75 -77.00 -90.00   94
 25  ω     36.00  62.00   0.50    4.00    --  107.75 -57.00 150.00   52
 26  ω    136.00 162.00   0.50    4.00    --  107.75 125.00-120.00   52
 27  ω    102.00 128.00   0.50    4.00    --  107.75 125.00-120.00   52
 28  ω     37.00  66.00   0.50    4.00    --  107.75 -57.00  60.00   58
 29  ω    126.00 165.00   0.50    4.00    --  107.75  19.00 -30.00   78
 30  ω     36.00  61.00   0.50    4.00    --  107.75 -57.00-180.00   50
 31  ω    131.00 159.00   0.50    4.00    --  107.75  77.00-120.00   56
 32  ω    103.00 129.00   0.50    4.00    --  107.75  77.00-120.00   52
 33  ω     35.00  60.00   0.50    4.00    --  107.75 -57.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0430130000
_diffrn_orient_matrix_UB_12      -0.0219340000
_diffrn_orient_matrix_UB_13      -0.0714051000
_diffrn_orient_matrix_UB_21      -0.0735785000
_diffrn_orient_matrix_UB_22      0.0516435000
_diffrn_orient_matrix_UB_23      -0.0461998000
_diffrn_orient_matrix_UB_31      0.0854538000
_diffrn_orient_matrix_UB_32      0.0555586000
_diffrn_orient_matrix_UB_33      0.0146310000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6299
_reflns_number_total             7932
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.497
_refine_diff_density_min         -1.138
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       0.0012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     611
_refine_ls_number_reflns         7932
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0990
_refine_ls_restrained_S_all      1.095
_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)+(0.1523P)²+7.1862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2847
_refine_ls_wR_factor_ref         0.2981
_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:
 C1S(H1SA,H1SB), C13(H13A,H13B), C15(H15A,H15B), C50(H50A,H50B), C52(H52A,H52B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C21(H21), C22(H22), C23(H23), C24(H24),
 C40(H40), C41(H41), C42(H42), C43(H43), C59(H59), C60(H60), C61(H61), C62(H62)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C56(H56A,H56B,
 H56C), C57(H57A,H57B,H57C), C65(H65A,H65B,H65C)
;
_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 0.6027(3) 0.58715(18) 0.60241(16) 0.1661(13) Uani 1 1 d . . . . .
Cl2 Cl 0.5773(4) 0.5681(2) 0.4441(2) 0.1984(18) Uani 1 1 d . . . . .
C1S C 0.5546(8) 0.6134(6) 0.5149(5) 0.132(3) Uani 1 1 d . . . . .
H1SA H 0.479185 0.617520 0.511892 0.159 Uiso 1 1 calc R U . . .
H1SB H 0.581564 0.659128 0.508706 0.159 Uiso 1 1 calc R U . . .
O1 O 0.2237(3) 0.24832(17) 0.70943(19) 0.0593(9) Uani 1 1 d . . . . .
O2 O -0.0329(3) 0.17398(18) 0.5424(2) 0.0684(10) Uani 1 1 d . . . . .
O3 O 0.2331(3) 0.27615(16) 0.46481(19) 0.0586(9) Uani 1 1 d . . . . .
O4 O 0.3508(3) 0.01480(17) 0.5250(2) 0.0634(9) Uani 1 1 d . . . . .
N1 N 0.0988(3) 0.11074(18) 0.6955(2) 0.0450(8) Uani 1 1 d . . . . .
C1 C 0.1931(3) 0.0221(2) 0.6559(2) 0.0447(10) Uani 1 1 d . . . . .
C2 C 0.2286(4) -0.0461(2) 0.6565(3) 0.0557(11) Uani 1 1 d . . . . .
H2 H 0.271157 -0.060736 0.622367 0.067 Uiso 1 1 calc R U . . .
C3 C 0.1994(4) -0.0905(3) 0.7081(3) 0.0637(13) Uani 1 1 d . . . . .
H3 H 0.221882 -0.135813 0.708537 0.076 Uiso 1 1 calc R U . . .
C4 C 0.1367(4) -0.0693(3) 0.7601(3) 0.0648(14) Uani 1 1 d . . . . .
H4 H 0.118592 -0.100853 0.794596 0.078 Uiso 1 1 calc R U . . .
C5 C 0.1006(4) -0.0027(2) 0.7620(3) 0.0537(11) Uani 1 1 d . . . . .
H5 H 0.059771 0.011479 0.797445 0.064 Uiso 1 1 calc R U . . .
C6 C 0.1283(3) 0.0422(2) 0.7083(2) 0.0466(10) Uani 1 1 d . . . . .
C7 C 0.1434(3) 0.1323(2) 0.6369(2) 0.0431(9) Uani 1 1 d . . . . .
C8 C 0.2026(3) 0.0816(2) 0.6112(2) 0.0418(9) Uani 1 1 d . . . . .
C9 C 0.2497(3) 0.1095(2) 0.5509(2) 0.0408(9) Uani 1 1 d . . . . .
C10 C 0.2204(3) 0.1767(2) 0.5378(2) 0.0393(9) Uani 1 1 d . . . . .
C11 C 0.1455(3) 0.1980(2) 0.5937(2) 0.0414(9) Uani 1 1 d . . . . .
C12 C 0.1878(3) 0.2589(2) 0.6448(2) 0.0435(9) Uani 1 1 d . . . . .
C13 C 0.1760(3) 0.3290(2) 0.6113(3) 0.0484(10) Uani 1 1 d . . . . .
H13A H 0.220301 0.332871 0.572629 0.058 Uiso 1 1 calc R U . . .
H13B H 0.199560 0.362604 0.649712 0.058 Uiso 1 1 calc R U . . .
C14 C 0.0618(3) 0.3446(2) 0.5772(3) 0.0482(10) Uani 1 1 d . . . . .
C15 C 0.0198(3) 0.2888(2) 0.5203(3) 0.0482(10) Uani 1 1 d . . . . .
H15A H -0.054515 0.296517 0.504259 0.058 Uiso 1 1 calc R U . . .
H15B H 0.054642 0.293200 0.476564 0.058 Uiso 1 1 calc R U . . .
C16 C 0.0351(3) 0.2167(2) 0.5502(2) 0.0435(9) Uani 1 1 d . . . . .
C17 C 0.2569(3) 0.2161(2) 0.4791(2) 0.0432(9) Uani 1 1 d . . . . .
C18 C 0.3290(3) 0.1800(2) 0.4340(2) 0.0441(9) Uani 1 1 d . . . . .
C19 C 0.3231(3) 0.0735(2) 0.5093(2) 0.0449(10) Uani 1 1 d . . . . .
C20 C 0.3614(3) 0.1122(2) 0.4477(2) 0.0443(9) Uani 1 1 d . . . . .
C21 C 0.4283(4) 0.0810(2) 0.4049(3) 0.0548(11) Uani 1 1 d . . . . .
H21 H 0.450710 0.036241 0.415080 0.066 Uiso 1 1 calc R U . . .
C22 C 0.4614(5) 0.1170(3) 0.3471(3) 0.0677(14) Uani 1 1 d . . . . .
H22 H 0.505229 0.096162 0.317342 0.081 Uiso 1 1 calc R U . . .
C23 C 0.4299(5) 0.1834(3) 0.3333(3) 0.0715(15) Uani 1 1 d . . . . .
H23 H 0.453755 0.207442 0.294788 0.086 Uiso 1 1 calc R U . . .
C24 C 0.3635(4) 0.2151(3) 0.3754(3) 0.0579(12) Uani 1 1 d . . . . .
H24 H 0.341877 0.259962 0.364704 0.070 Uiso 1 1 calc R U . . .
C25 C -0.0061(5) 0.3470(3) 0.6401(3) 0.0709(15) Uani 1 1 d . . . . .
H25A H -0.077354 0.357014 0.619073 0.106 Uiso 1 1 calc R U . . .
H25B H 0.019805 0.381929 0.675433 0.106 Uiso 1 1 calc R U . . .
H25C H -0.003193 0.303400 0.664951 0.106 Uiso 1 1 calc R U . . .
C26 C 0.0590(5) 0.4136(3) 0.5377(3) 0.0715(15) Uani 1 1 d . . . . .
H26A H 0.102986 0.411957 0.499364 0.107 Uiso 1 1 calc R U . . .
H26B H 0.084065 0.448573 0.573393 0.107 Uiso 1 1 calc R U . . .
H26C H -0.011621 0.423911 0.515516 0.107 Uiso 1 1 calc R U . . .
C27 C 0.0302(4) 0.1496(3) 0.7368(3) 0.0553(11) Uani 1 1 d . . . . .
H27A H -0.033750 0.160304 0.704337 0.083 Uiso 1 1 calc R U . . .
H27B H 0.064443 0.191214 0.755087 0.083 Uiso 1 1 calc R U . . .
H27C H 0.014540 0.122783 0.778312 0.083 Uiso 1 1 calc R U . . .
O54 O 0.4429(3) 0.2425(2) 0.6124(2) 0.0840(13) Uani 1 1 d . . . . .
O55 O 0.7702(2) 0.18200(18) 0.7181(2) 0.0638(9) Uani 1 1 d . . . . .
O66 O 0.7517(3) 0.46856(19) 0.6824(2) 0.0757(11) Uani 1 1 d . . . . .
O67 O 0.5562(3) 0.28987(17) 0.8405(2) 0.0632(9) Uani 1 1 d . . . . .
N64 N 0.6623(3) 0.2366(2) 0.5493(2) 0.0555(10) Uani 1 1 d . . . . .
C36 C 0.6123(3) 0.2454(2) 0.6856(2) 0.0444(9) Uani 1 1 d . . . . .
C37 C 0.6251(3) 0.3150(2) 0.7292(2) 0.0442(9) Uani 1 1 d . . . . .
C38 C 0.5958(3) 0.3313(2) 0.8016(2) 0.0449(10) Uani 1 1 d . . . . .
C39 C 0.6132(3) 0.4040(2) 0.8277(3) 0.0465(10) Uani 1 1 d . . . . .
C40 C 0.5777(4) 0.4248(2) 0.8927(3) 0.0517(11) Uani 1 1 d . . . . .
H40 H 0.543707 0.393674 0.919817 0.062 Uiso 1 1 calc R U . . .
C41 C 0.5925(4) 0.4916(3) 0.9175(3) 0.0600(12) Uani 1 1 d . . . . .
H41 H 0.568809 0.505217 0.961343 0.072 Uiso 1 1 calc R U . . .
C42 C 0.6426(4) 0.5382(3) 0.8773(3) 0.0610(13) Uani 1 1 d . . . . .
H42 H 0.652308 0.583119 0.894080 0.073 Uiso 1 1 calc R U . . .
C43 C 0.6776(4) 0.5185(2) 0.8136(3) 0.0550(11) Uani 1 1 d . . . . .
H43 H 0.711364 0.550055 0.786947 0.066 Uiso 1 1 calc R U . . .
C44 C 0.6634(3) 0.4511(2) 0.7873(3) 0.0472(10) Uani 1 1 d . . . . .
C45 C 0.6988(4) 0.4315(2) 0.7162(3) 0.0510(11) Uani 1 1 d . . . . .
C46 C 0.6686(3) 0.3624(2) 0.6877(2) 0.0446(9) Uani 1 1 d . . . . .
C47 C 0.6843(3) 0.3339(2) 0.6167(3) 0.0499(10) Uani 1 1 d . . . . .
C48 C 0.6532(4) 0.2666(2) 0.6158(3) 0.0512(11) Uani 1 1 d . . . . .
C49 C 0.4943(3) 0.2238(2) 0.6701(3) 0.0523(11) Uani 1 1 d . . . . .
C50 C 0.4528(3) 0.1812(2) 0.7268(3) 0.0535(11) Uani 1 1 d . . . . .
H50A H 0.385312 0.162743 0.704816 0.064 Uiso 1 1 calc R U . . .
H50B H 0.441391 0.210217 0.768454 0.064 Uiso 1 1 calc R U . . .
C51 C 0.5251(3) 0.1212(2) 0.7573(3) 0.0497(10) Uani 1 1 d . . . . .
C52 C 0.6346(3) 0.1495(2) 0.7869(3) 0.0475(10) Uani 1 1 d . . . . .
H52A H 0.630023 0.178080 0.830191 0.057 Uiso 1 1 calc R U . . .
H52B H 0.680811 0.111479 0.803313 0.057 Uiso 1 1 calc R U . . .
C53 C 0.6816(3) 0.1902(2) 0.7311(2) 0.0454(10) Uani 1 1 d . . . . .
C56 C 0.4806(5) 0.0865(3) 0.8217(3) 0.0682(14) Uani 1 1 d . . . . .
H56A H 0.526859 0.050368 0.842089 0.102 Uiso 1 1 calc R U . . .
H56B H 0.412815 0.067748 0.803373 0.102 Uiso 1 1 calc R U . . .
H56C H 0.474333 0.119560 0.860134 0.102 Uiso 1 1 calc R U . . .
C57 C 0.5317(4) 0.0688(3) 0.6959(3) 0.0621(13) Uani 1 1 d . . . . .
H57A H 0.560582 0.090020 0.655585 0.093 Uiso 1 1 calc R U . . .
H57B H 0.462808 0.051776 0.677504 0.093 Uiso 1 1 calc R U . . .
H57C H 0.575927 0.031517 0.715701 0.093 Uiso 1 1 calc R U . . .
C58 C 0.6990(4) 0.2865(3) 0.5042(3) 0.0558(12) Uani 1 1 d . . . . .
C59 C 0.7168(4) 0.2805(3) 0.4313(3) 0.0685(14) Uani 1 1 d . . . . .
H59 H 0.709401 0.238816 0.406156 0.082 Uiso 1 1 calc R U . . .
C60 C 0.7462(4) 0.3394(4) 0.3970(3) 0.0767(17) Uani 1 1 d . . . . .
H60 H 0.756612 0.337342 0.347243 0.092 Uiso 1 1 calc R U . . .
C61 C 0.7606(4) 0.4011(4) 0.4347(3) 0.0735(16) Uani 1 1 d . . . . .
H61 H 0.781250 0.439384 0.409940 0.088 Uiso 1 1 calc R U . . .
C62 C 0.7450(4) 0.4068(3) 0.5081(3) 0.0623(13) Uani 1 1 d . . . . .
H62 H 0.755582 0.448440 0.533150 0.075 Uiso 1 1 calc R U . . .
C63 C 0.7127(3) 0.3488(3) 0.5445(3) 0.0544(11) Uani 1 1 d . . . . .
C65 C 0.6391(5) 0.1661(3) 0.5273(3) 0.0771(16) Uani 1 1 d . . . . .
H65A H 0.647803 0.137412 0.571008 0.116 Uiso 1 1 calc R U . . .
H65B H 0.686043 0.151263 0.494037 0.116 Uiso 1 1 calc R U . . .
H65C H 0.568121 0.162851 0.502282 0.116 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 C1S 1.688(10) . ?
Cl2 C1S 1.618(10) . ?
C1S H1SA 0.9700 . ?
C1S H1SB 0.9700 . ?
O1 C12 1.207(5) . ?
O2 C16 1.204(5) . ?
O3 C17 1.230(5) . ?
O4 C19 1.222(5) . ?
N1 C6 1.401(5) . ?
N1 C7 1.346(6) . ?
N1 C27 1.455(6) . ?
C1 C2 1.408(6) . ?
C1 C6 1.411(6) . ?
C1 C8 1.431(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(6) . ?
C7 C8 1.374(6) . ?
C7 C11 1.504(6) . ?
C8 C9 1.432(6) . ?
C9 C10 1.377(6) . ?
C9 C19 1.473(6) . ?
C10 C11 1.556(6) . ?
C10 C17 1.446(6) . ?
C11 C12 1.552(6) . ?
C11 C16 1.562(5) . ?
C12 C13 1.494(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.540(6) . ?
C14 C15 1.538(6) . ?
C14 C25 1.537(7) . ?
C14 C26 1.523(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.510(6) . ?
C17 C18 1.503(6) . ?
C18 C20 1.398(6) . ?
C18 C24 1.390(6) . ?
C19 C20 1.490(6) . ?
C20 C21 1.385(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.370(8) . ?
C23 H23 0.9300 . ?
C23 C24 1.376(7) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
O54 C49 1.203(6) . ?
O55 C53 1.211(5) . ?
O66 C45 1.220(6) . ?
O67 C38 1.232(5) . ?
N64 C48 1.356(6) . ?
N64 C58 1.399(6) . ?
N64 C65 1.452(7) . ?
C36 C37 1.568(6) . ?
C36 C48 1.498(7) . ?
C36 C49 1.563(6) . ?
C36 C53 1.554(6) . ?
C37 C38 1.449(6) . ?
C37 C46 1.364(6) . ?
C38 C39 1.502(6) . ?
C39 C40 1.385(6) . ?
C39 C44 1.393(6) . ?
C40 H40 0.9300 . ?
C40 C41 1.383(7) . ?
C41 H41 0.9300 . ?
C41 C42 1.384(8) . ?
C42 H42 0.9300 . ?
C42 C43 1.354(7) . ?
C43 H43 0.9300 . ?
C43 C44 1.402(6) . ?
C44 C45 1.476(7) . ?
C45 C46 1.477(6) . ?
C46 C47 1.440(6) . ?
C47 C48 1.373(6) . ?
C47 C63 1.437(7) . ?
C49 C50 1.482(7) . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
C50 C51 1.546(6) . ?
C51 C52 1.535(6) . ?
C51 C56 1.532(7) . ?
C51 C57 1.522(7) . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
C52 C53 1.483(6) . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?
C58 C59 1.376(7) . ?
C58 C63 1.414(7) . ?
C59 H59 0.9300 . ?
C59 C60 1.386(9) . ?
C60 H60 0.9300 . ?
C60 C61 1.381(9) . ?
C61 H61 0.9300 . ?
C61 C62 1.376(8) . ?
C62 H62 0.9300 . ?
C62 C63 1.405(7) . ?
C65 H65A 0.9600 . ?
C65 H65B 0.9600 . ?
C65 H65C 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
Cl1 C1S H1SA 107.5 . . ?
Cl1 C1S H1SB 107.5 . . ?
Cl2 C1S Cl1 119.3(7) . . ?
Cl2 C1S H1SA 107.5 . . ?
Cl2 C1S H1SB 107.5 . . ?
H1SA C1S H1SB 107.0 . . ?
C6 N1 C27 125.7(4) . . ?
C7 N1 C6 106.9(3) . . ?
C7 N1 C27 127.3(4) . . ?
C2 C1 C6 118.9(4) . . ?
C2 C1 C8 135.8(4) . . ?
C6 C1 C8 105.3(4) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.8(5) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.3(5) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.0 . . ?
C5 C4 C3 121.9(5) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 121.6 . . ?
C4 C5 C6 116.8(5) . . ?
C6 C5 H5 121.6 . . ?
N1 C6 C1 109.1(4) . . ?
C5 C6 N1 128.6(4) . . ?
C5 C6 C1 122.3(4) . . ?
N1 C7 C8 111.5(4) . . ?
N1 C7 C11 135.9(4) . . ?
C8 C7 C11 112.6(4) . . ?
C1 C8 C9 145.1(4) . . ?
C7 C8 C1 107.1(4) . . ?
C7 C8 C9 107.8(4) . . ?
C8 C9 C19 125.9(4) . . ?
C10 C9 C8 110.8(4) . . ?
C10 C9 C19 123.2(4) . . ?
C9 C10 C11 109.0(3) . . ?
C9 C10 C17 121.4(4) . . ?
C17 C10 C11 129.6(3) . . ?
C7 C11 C10 99.8(3) . . ?
C7 C11 C12 112.2(3) . . ?
C7 C11 C16 112.0(3) . . ?
C10 C11 C16 110.1(3) . . ?
C12 C11 C10 113.2(3) . . ?
C12 C11 C16 109.4(3) . . ?
O1 C12 C11 119.5(4) . . ?
O1 C12 C13 123.3(4) . . ?
C13 C12 C11 117.1(4) . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C12 C13 C14 112.0(4) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C15 C14 C13 110.2(3) . . ?
C25 C14 C13 109.2(4) . . ?
C25 C14 C15 109.4(4) . . ?
C26 C14 C13 108.4(4) . . ?
C26 C14 C15 109.5(4) . . ?
C26 C14 C25 110.1(4) . . ?
C14 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C14 114.0(4) . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
O2 C16 C11 119.4(4) . . ?
O2 C16 C15 123.4(4) . . ?
C15 C16 C11 117.3(3) . . ?
O3 C17 C10 124.2(4) . . ?
O3 C17 C18 119.3(4) . . ?
C10 C17 C18 116.5(3) . . ?
C20 C18 C17 122.7(4) . . ?
C24 C18 C17 118.5(4) . . ?
C24 C18 C20 118.7(4) . . ?
O4 C19 C9 121.1(4) . . ?
O4 C19 C20 122.1(4) . . ?
C9 C19 C20 116.8(3) . . ?
C18 C20 C19 119.2(4) . . ?
C21 C20 C18 120.8(4) . . ?
C21 C20 C19 119.9(4) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.3(5) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.1(5) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.4 . . ?
C22 C23 C24 121.3(5) . . ?
C24 C23 H23 119.4 . . ?
C18 C24 H24 120.1 . . ?
C23 C24 C18 119.7(5) . . ?
C23 C24 H24 120.1 . . ?
C14 C25 H25A 109.5 . . ?
C14 C25 H25B 109.5 . . ?
C14 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C14 C26 H26A 109.5 . . ?
C14 C26 H26B 109.5 . . ?
C14 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N1 C27 H27A 109.5 . . ?
N1 C27 H27B 109.5 . . ?
N1 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C48 N64 C58 107.2(4) . . ?
C48 N64 C65 127.6(4) . . ?
C58 N64 C65 125.1(4) . . ?
C48 C36 C37 99.2(3) . . ?
C48 C36 C49 112.5(4) . . ?
C48 C36 C53 112.9(4) . . ?
C49 C36 C37 110.4(3) . . ?
C53 C36 C37 109.1(3) . . ?
C53 C36 C49 112.0(3) . . ?
C38 C37 C36 128.4(4) . . ?
C46 C37 C36 109.4(4) . . ?
C46 C37 C38 122.2(4) . . ?
O67 C38 C37 123.9(4) . . ?
O67 C38 C39 119.8(4) . . ?
C37 C38 C39 116.3(4) . . ?
C40 C39 C38 119.3(4) . . ?
C40 C39 C44 119.4(4) . . ?
C44 C39 C38 121.2(4) . . ?
C39 C40 H40 119.9 . . ?
C41 C40 C39 120.2(5) . . ?
C41 C40 H40 119.9 . . ?
C40 C41 H41 119.9 . . ?
C40 C41 C42 120.2(5) . . ?
C42 C41 H41 119.9 . . ?
C41 C42 H42 120.0 . . ?
C43 C42 C41 120.1(5) . . ?
C43 C42 H42 120.0 . . ?
C42 C43 H43 119.6 . . ?
C42 C43 C44 120.8(5) . . ?
C44 C43 H43 119.6 . . ?
C39 C44 C43 119.3(4) . . ?
C39 C44 C45 121.0(4) . . ?
C43 C44 C45 119.7(4) . . ?
O66 C45 C44 123.6(4) . . ?
O66 C45 C46 120.3(4) . . ?
C44 C45 C46 116.1(4) . . ?
C37 C46 C45 122.5(4) . . ?
C37 C46 C47 110.7(4) . . ?
C47 C46 C45 126.8(4) . . ?
C48 C47 C46 107.4(4) . . ?
C48 C47 C63 107.3(4) . . ?
C63 C47 C46 145.1(4) . . ?
N64 C48 C36 135.6(4) . . ?
N64 C48 C47 111.1(4) . . ?
C47 C48 C36 113.2(4) . . ?
O54 C49 C36 117.9(4) . . ?
O54 C49 C50 124.0(4) . . ?
C50 C49 C36 118.1(4) . . ?
C49 C50 H50A 108.7 . . ?
C49 C50 H50B 108.7 . . ?
C49 C50 C51 114.2(4) . . ?
H50A C50 H50B 107.6 . . ?
C51 C50 H50A 108.7 . . ?
C51 C50 H50B 108.7 . . ?
C52 C51 C50 109.0(3) . . ?
C56 C51 C50 109.3(4) . . ?
C56 C51 C52 109.0(4) . . ?
C57 C51 C50 110.3(4) . . ?
C57 C51 C52 110.2(4) . . ?
C57 C51 C56 109.0(4) . . ?
C51 C52 H52A 108.8 . . ?
C51 C52 H52B 108.8 . . ?
H52A C52 H52B 107.7 . . ?
C53 C52 C51 113.9(4) . . ?
C53 C52 H52A 108.8 . . ?
C53 C52 H52B 108.8 . . ?
O55 C53 C36 118.3(4) . . ?
O55 C53 C52 123.8(4) . . ?
C52 C53 C36 117.9(4) . . ?
C51 C56 H56A 109.5 . . ?
C51 C56 H56B 109.5 . . ?
C51 C56 H56C 109.5 . . ?
H56A C56 H56B 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C51 C57 H57A 109.5 . . ?
C51 C57 H57B 109.5 . . ?
C51 C57 H57C 109.5 . . ?
H57A C57 H57B 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
N64 C58 C63 109.1(4) . . ?
C59 C58 N64 128.2(5) . . ?
C59 C58 C63 122.7(5) . . ?
C58 C59 H59 121.5 . . ?
C58 C59 C60 117.0(6) . . ?
C60 C59 H59 121.5 . . ?
C59 C60 H60 119.0 . . ?
C61 C60 C59 121.9(6) . . ?
C61 C60 H60 119.0 . . ?
C60 C61 H61 119.4 . . ?
C62 C61 C60 121.1(6) . . ?
C62 C61 H61 119.4 . . ?
C61 C62 H62 120.6 . . ?
C61 C62 C63 118.9(6) . . ?
C63 C62 H62 120.6 . . ?
C58 C63 C47 105.3(4) . . ?
C62 C63 C47 136.3(5) . . ?
C62 C63 C58 118.4(5) . . ?
N64 C65 H65A 109.5 . . ?
N64 C65 H65B 109.5 . . ?
N64 C65 H65C 109.5 . . ?
H65A C65 H65B 109.5 . . ?
H65A C65 H65C 109.5 . . ?
H65B C65 H65C 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
O1 C12 C13 C14 -122.7(5) . . . . ?
O3 C17 C18 C20 178.7(4) . . . . ?
O3 C17 C18 C24 -2.4(6) . . . . ?
O4 C19 C20 C18 -178.2(4) . . . . ?
O4 C19 C20 C21 1.7(6) . . . . ?
N1 C7 C8 C1 1.4(5) . . . . ?
N1 C7 C8 C9 -178.1(3) . . . . ?
N1 C7 C11 C10 177.8(5) . . . . ?
N1 C7 C11 C12 57.7(6) . . . . ?
N1 C7 C11 C16 -65.7(6) . . . . ?
C1 C2 C3 C4 -0.7(8) . . . . ?
C1 C8 C9 C10 -179.7(6) . . . . ?
C1 C8 C9 C19 -1.9(9) . . . . ?
C2 C1 C6 N1 -177.4(4) . . . . ?
C2 C1 C6 C5 1.9(7) . . . . ?
C2 C1 C8 C7 176.3(5) . . . . ?
C2 C1 C8 C9 -4.7(10) . . . . ?
C2 C3 C4 C5 0.3(8) . . . . ?
C3 C4 C5 C6 1.2(7) . . . . ?
C4 C5 C6 N1 176.8(4) . . . . ?
C4 C5 C6 C1 -2.3(7) . . . . ?
C6 N1 C7 C8 -1.0(5) . . . . ?
C6 N1 C7 C11 179.9(5) . . . . ?
C6 C1 C2 C3 -0.3(7) . . . . ?
C6 C1 C8 C7 -1.1(5) . . . . ?
C6 C1 C8 C9 178.0(6) . . . . ?
C7 N1 C6 C1 0.3(5) . . . . ?
C7 N1 C6 C5 -178.9(4) . . . . ?
C7 C8 C9 C10 -0.6(5) . . . . ?
C7 C8 C9 C19 177.2(4) . . . . ?
C7 C11 C12 O1 7.3(6) . . . . ?
C7 C11 C12 C13 -169.5(4) . . . . ?
C7 C11 C16 O2 -14.2(6) . . . . ?
C7 C11 C16 C15 165.4(4) . . . . ?
C8 C1 C2 C3 -177.5(5) . . . . ?
C8 C1 C6 N1 0.5(5) . . . . ?
C8 C1 C6 C5 179.8(4) . . . . ?
C8 C7 C11 C10 -1.3(4) . . . . ?
C8 C7 C11 C12 -121.4(4) . . . . ?
C8 C7 C11 C16 115.3(4) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C8 C9 C10 C17 -179.4(3) . . . . ?
C8 C9 C19 O4 -0.9(7) . . . . ?
C8 C9 C19 C20 179.1(4) . . . . ?
C9 C10 C11 C7 0.8(4) . . . . ?
C9 C10 C11 C12 120.2(4) . . . . ?
C9 C10 C11 C16 -117.0(4) . . . . ?
C9 C10 C17 O3 179.8(4) . . . . ?
C9 C10 C17 C18 -0.6(6) . . . . ?
C9 C19 C20 C18 1.8(6) . . . . ?
C9 C19 C20 C21 -178.3(4) . . . . ?
C10 C9 C19 O4 176.6(4) . . . . ?
C10 C9 C19 C20 -3.3(6) . . . . ?
C10 C11 C12 O1 -104.7(5) . . . . ?
C10 C11 C12 C13 78.6(4) . . . . ?
C10 C11 C16 O2 95.9(5) . . . . ?
C10 C11 C16 C15 -84.5(4) . . . . ?
C10 C17 C18 C20 -0.9(6) . . . . ?
C10 C17 C18 C24 178.0(4) . . . . ?
C11 C7 C8 C1 -179.3(3) . . . . ?
C11 C7 C8 C9 1.2(5) . . . . ?
C11 C10 C17 O3 0.9(7) . . . . ?
C11 C10 C17 C18 -179.5(4) . . . . ?
C11 C12 C13 C14 53.9(5) . . . . ?
C12 C11 C16 O2 -139.2(4) . . . . ?
C12 C11 C16 C15 40.4(5) . . . . ?
C12 C13 C14 C15 -54.6(5) . . . . ?
C12 C13 C14 C25 65.6(5) . . . . ?
C12 C13 C14 C26 -174.4(4) . . . . ?
C13 C14 C15 C16 51.4(5) . . . . ?
C14 C15 C16 O2 133.1(5) . . . . ?
C14 C15 C16 C11 -46.5(5) . . . . ?
C16 C11 C12 O1 132.1(4) . . . . ?
C16 C11 C12 C13 -44.6(5) . . . . ?
C17 C10 C11 C7 179.9(4) . . . . ?
C17 C10 C11 C12 -60.7(5) . . . . ?
C17 C10 C11 C16 62.0(5) . . . . ?
C17 C18 C20 C19 0.2(6) . . . . ?
C17 C18 C20 C21 -179.7(4) . . . . ?
C17 C18 C24 C23 179.8(5) . . . . ?
C18 C20 C21 C22 -1.4(7) . . . . ?
C19 C9 C10 C11 -178.1(4) . . . . ?
C19 C9 C10 C17 2.7(6) . . . . ?
C19 C20 C21 C22 178.7(4) . . . . ?
C20 C18 C24 C23 -1.2(7) . . . . ?
C20 C21 C22 C23 1.3(8) . . . . ?
C21 C22 C23 C24 -1.2(9) . . . . ?
C22 C23 C24 C18 1.2(9) . . . . ?
C24 C18 C20 C19 -178.7(4) . . . . ?
C24 C18 C20 C21 1.4(6) . . . . ?
C25 C14 C15 C16 -68.7(5) . . . . ?
C26 C14 C15 C16 170.5(4) . . . . ?
C27 N1 C6 C1 178.6(4) . . . . ?
C27 N1 C6 C5 -0.7(7) . . . . ?
C27 N1 C7 C8 -179.3(4) . . . . ?
C27 N1 C7 C11 1.6(8) . . . . ?
O54 C49 C50 C51 134.8(5) . . . . ?
O66 C45 C46 C37 168.7(5) . . . . ?
O66 C45 C46 C47 -8.1(7) . . . . ?
O67 C38 C39 C40 -4.6(6) . . . . ?
O67 C38 C39 C44 176.1(4) . . . . ?
N64 C58 C59 C60 175.5(5) . . . . ?
N64 C58 C63 C47 1.0(5) . . . . ?
N64 C58 C63 C62 -177.3(4) . . . . ?
C36 C37 C38 O67 1.1(7) . . . . ?
C36 C37 C38 C39 -177.2(4) . . . . ?
C36 C37 C46 C45 -174.8(4) . . . . ?
C36 C37 C46 C47 2.4(5) . . . . ?
C36 C49 C50 C51 -44.7(6) . . . . ?
C37 C36 C48 N64 -175.5(5) . . . . ?
C37 C36 C48 C47 0.1(5) . . . . ?
C37 C36 C49 O54 90.8(5) . . . . ?
C37 C36 C49 C50 -89.7(5) . . . . ?
C37 C36 C53 O55 -91.7(5) . . . . ?
C37 C36 C53 C52 89.4(4) . . . . ?
C37 C38 C39 C40 173.8(4) . . . . ?
C37 C38 C39 C44 -5.5(6) . . . . ?
C37 C46 C47 C48 -2.3(5) . . . . ?
C37 C46 C47 C63 171.4(6) . . . . ?
C38 C37 C46 C45 6.2(6) . . . . ?
C38 C37 C46 C47 -176.6(4) . . . . ?
C38 C39 C40 C41 -179.7(4) . . . . ?
C38 C39 C44 C43 179.7(4) . . . . ?
C38 C39 C44 C45 1.7(6) . . . . ?
C39 C40 C41 C42 0.3(7) . . . . ?
C39 C44 C45 O66 -172.8(5) . . . . ?
C39 C44 C45 C46 5.7(6) . . . . ?
C40 C39 C44 C43 0.4(6) . . . . ?
C40 C39 C44 C45 -177.6(4) . . . . ?
C40 C41 C42 C43 -0.2(8) . . . . ?
C41 C42 C43 C44 0.2(7) . . . . ?
C42 C43 C44 C39 -0.3(7) . . . . ?
C42 C43 C44 C45 177.8(4) . . . . ?
C43 C44 C45 O66 9.2(7) . . . . ?
C43 C44 C45 C46 -172.3(4) . . . . ?
C44 C39 C40 C41 -0.4(6) . . . . ?
C44 C45 C46 C37 -9.8(6) . . . . ?
C44 C45 C46 C47 173.4(4) . . . . ?
C45 C46 C47 C48 174.8(4) . . . . ?
C45 C46 C47 C63 -11.5(9) . . . . ?
C46 C37 C38 O67 179.9(4) . . . . ?
C46 C37 C38 C39 1.6(6) . . . . ?
C46 C47 C48 N64 178.0(4) . . . . ?
C46 C47 C48 C36 1.2(5) . . . . ?
C46 C47 C63 C58 -175.3(6) . . . . ?
C46 C47 C63 C62 2.5(11) . . . . ?
C48 N64 C58 C59 -177.6(5) . . . . ?
C48 N64 C58 C63 0.1(5) . . . . ?
C48 C36 C37 C38 177.4(4) . . . . ?
C48 C36 C37 C46 -1.5(4) . . . . ?
C48 C36 C49 O54 -19.0(6) . . . . ?
C48 C36 C49 C50 160.5(4) . . . . ?
C48 C36 C53 O55 17.5(6) . . . . ?
C48 C36 C53 C52 -161.3(4) . . . . ?
C48 C47 C63 C58 -1.6(5) . . . . ?
C48 C47 C63 C62 176.2(5) . . . . ?
C49 C36 C37 C38 59.1(5) . . . . ?
C49 C36 C37 C46 -119.8(4) . . . . ?
C49 C36 C48 N64 -58.8(7) . . . . ?
C49 C36 C48 C47 116.9(4) . . . . ?
C49 C36 C53 O55 145.7(4) . . . . ?
C49 C36 C53 C52 -33.2(5) . . . . ?
C49 C50 C51 C52 54.2(5) . . . . ?
C49 C50 C51 C56 173.3(4) . . . . ?
C49 C50 C51 C57 -67.0(5) . . . . ?
C50 C51 C52 C53 -55.3(5) . . . . ?
C51 C52 C53 O55 -131.7(5) . . . . ?
C51 C52 C53 C36 47.1(5) . . . . ?
C53 C36 C37 C38 -64.4(5) . . . . ?
C53 C36 C37 C46 116.7(4) . . . . ?
C53 C36 C48 N64 69.1(6) . . . . ?
C53 C36 C48 C47 -115.2(4) . . . . ?
C53 C36 C49 O54 -147.3(5) . . . . ?
C53 C36 C49 C50 32.1(6) . . . . ?
C56 C51 C52 C53 -174.5(4) . . . . ?
C57 C51 C52 C53 65.9(5) . . . . ?
C58 N64 C48 C36 174.6(5) . . . . ?
C58 N64 C48 C47 -1.1(5) . . . . ?
C58 C59 C60 C61 2.1(8) . . . . ?
C59 C58 C63 C47 178.8(4) . . . . ?
C59 C58 C63 C62 0.5(7) . . . . ?
C59 C60 C61 C62 -0.8(9) . . . . ?
C60 C61 C62 C63 -0.7(8) . . . . ?
C61 C62 C63 C47 -176.8(5) . . . . ?
C61 C62 C63 C58 0.8(7) . . . . ?
C63 C47 C48 N64 1.8(5) . . . . ?
C63 C47 C48 C36 -175.0(4) . . . . ?
C63 C58 C59 C60 -2.0(7) . . . . ?
C65 N64 C48 C36 -5.4(9) . . . . ?
C65 N64 C48 C47 178.9(5) . . . . ?
C65 N64 C58 C59 2.4(8) . . . . ?
C65 N64 C58 C63 -179.9(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.922
_oxdiff_exptl_absorpt_empirical_full_min 0.271
