# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_3-co2ph_auto
_database_code_depnum_ccdc_archive 'CCDC 2380268'
loop_
_audit_author_name
_audit_author_address
'Chaochao Zhang'
;West China School of Pharmacy
China
;
_audit_update_record             
;
2024-08-28 deposited with the CCDC.	2024-11-04 downloaded from the CCDC.
;
_audit_creation_date             2024-07-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H Cl3, C33 H22 N2 O7'
_chemical_formula_sum            'C34 H23 Cl3 N2 O7'
_chemical_formula_weight         677.89
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONCl
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      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                   11.40750(10)
_cell_length_b                   12.09380(10)
_cell_length_c                   13.11160(10)
_cell_angle_alpha                81.5570(10)
_cell_angle_beta                 67.5690(10)
_cell_angle_gamma                73.6290(10)
_cell_volume                     1602.65(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    35884
_cell_measurement_temperature    300.57(10)
_cell_measurement_theta_max      75.6720
_cell_measurement_theta_min      3.7940
_shelx_estimated_absorpt_T_max   0.612
_shelx_estimated_absorpt_T_min   0.518
_exptl_absorpt_coefficient_mu    3.028
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            46997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.823
_diffrn_reflns_theta_min         3.813
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.57(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 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00  66.00   0.50    0.05    --   66.00  76.00   1.65   52
  2  ω     35.00  75.00   0.50    0.05    --   62.00  77.00 114.11   80
  3  ω     81.00 128.00   0.50    0.05    --   62.00  77.00 114.11   94
  4  ω    107.00 133.00   0.50    0.05    --   66.00  76.00   1.65   52
  5  ω     71.00 115.00   0.50    0.05    --   44.45  37.00  60.00   88
  6  ω     25.00  57.00   0.50    0.05    --   44.45  37.00  60.00   64
  7  ω     38.00  72.00   0.50    0.05    --   66.00  80.00-122.40   68
  8  ω      2.00  27.00   0.50    0.05    --   38.00  97.00 -72.96   50
  9  ω      8.00  33.00   0.50    0.05    --   42.00  93.00 124.91   50
 10  ω     18.00  43.00   0.50    0.05    --   50.00  89.00  88.71   50
 11  ω     18.00  43.00   0.50    0.05    --   50.00  89.00  27.73   50
 12  ω     18.00  43.00   0.50    0.05    --   50.00  88.00   1.70   50
 13  ω      3.00  28.00   0.50    0.05    --   34.00  86.00   9.52   50
 14  ω     18.00  43.00   0.50    0.05    --   50.00  89.00-116.67   50
 15  ω     15.00  40.00   0.50    0.05    --   46.00  86.00-179.28   50
 16  ω     20.00  45.00   0.50    0.05    --   50.00  88.00-167.41   50
 17  ω    100.00 126.00   0.50    0.11    --  107.48  90.00-170.00   52
 18  ω     29.00  55.00   0.50    0.05    --   58.00  81.00 -62.92   52
 19  ω     29.00  91.00   0.50    0.05    --   58.00  81.00 172.23  124
 20  ω     98.00 128.00   0.50    0.05    --   58.00  81.00 172.23   60
 21  ω    -23.00  43.00   0.50    0.05    --   44.45 -37.00 120.00  132
 22  ω     51.00 117.00   0.50    0.11    --  107.48-125.00 -90.00  132
 23  ω     39.00 114.00   0.50    0.11    --  107.48-125.00-120.00  150
 24  ω     35.00  70.00   0.50    0.11    --  107.48 -61.00-150.00   70
 25  ω     35.00  60.00   0.50    0.11    --  107.48 -61.00 -90.00   50
 26  ω     34.00  87.00   0.50    0.11    --  107.48 -90.00  74.00  106
 27  ω     39.00  97.00   0.50    0.11    --  107.48 -94.00  30.00  116
 28  ω     45.00 107.00   0.50    0.11    --  107.48 -94.00 -30.00  124
 29  ω     36.00 100.00   0.50    0.11    --  107.48 -94.00 -60.00  128
 30  ω    -22.00  75.00   0.50    0.05    --   44.45 -90.00  74.00  194
 31  ω   -103.00 -77.00   0.50    0.05    --  -44.45 -57.00   0.00   52
 32  ω    -53.00 -27.00   0.50    0.05    --  -44.45 -57.00   0.00   52
 33  ω    -69.00 -25.00   0.50    0.05    --  -44.45 -57.00 -90.00   88
 34  ω    -48.00 -20.00   0.50    0.05    --  -44.45 -19.00-120.00   56
 35  ω    -51.00 -25.00   0.50    0.05    --  -44.45 -57.00-180.00   52
 36  ω   -117.00 -59.00   0.50    0.05    --  -44.45 -57.00-180.00  116
 37  ω   -121.00 -92.00   0.50    0.05    --  -44.45 -19.00-120.00   58
 38  ω   -154.00 -77.00   0.50    0.11    -- -102.00 -90.00  74.00  154
 39  ω    -70.00 -44.00   0.50    0.11    --  -74.00 -83.00  80.02   52
 40  ω    -58.00 -32.00   0.50    0.05    --  -62.00 -83.00  44.89   52
 41  ω    -70.00 -44.00   0.50    0.11    --  -74.00 -83.00  15.19   52
 42  ω    -54.00 -29.00   0.50    0.05    --  -58.00 -82.00 -36.94   50
 43  ω    -70.00 -33.00   0.50    0.05    --  -62.00 -82.00 -66.90   74
 44  ω   -119.00 -85.00   0.50    0.05    --  -58.00 -83.00-158.46   68
 45  ω    -83.00 -49.00   0.50    0.11    --  -78.00 -82.00-172.86   68
 46  ω    -53.00 -28.00   0.50    0.05    --  -58.00 -83.00-158.46   50
 47  ω    -76.00 -41.00   0.50    0.05    --  -70.00 -81.00 176.80   70
 48  ω   -135.00-109.00   0.50    0.05    --  -70.00 -81.00 176.80   52
 49  ω   -171.00-119.00   0.50    0.11    --  -98.00 -57.00 166.55  104
 50  ω    -79.00 -54.00   0.50    0.11    --  -82.00 -79.00  61.21   50
 51  ω   -105.00 -70.00   0.50    0.11    --  -98.00 -78.00   0.28   70
 52  ω   -112.00 -70.00   0.50    0.11    --  -98.00 -78.00 -38.19   84
 53  ω    -68.00 -42.00   0.50    0.05    --  -70.00 -80.00 -62.29   52
 54  ω   -169.00 -70.00   0.50    0.11    --  -98.00 -78.00 -70.94  198
 55  ω   -171.00-131.00   0.50    0.11    --  -98.00 -78.00 -38.19   80
 56  ω   -171.00-140.00   0.50    0.11    --  -98.00 -77.00-153.03   62
 57  ω   -134.00 -71.00   0.50    0.11    --  -98.00 -77.00-153.03  126
 58  ω   -103.00 -78.00   0.50    0.11    -- -102.00 -77.00-120.00   50
 59  ω   -175.00 -74.00   0.50    0.11    -- -102.00 -78.00 -23.93  202
 60  ω   -171.00-110.00   0.50    0.11    --  -98.00 -78.00   0.28  122
 61  ω    -89.00 -59.00   0.50    0.11    --  -86.00 -77.00  99.17   60
 62  ω   -155.00 -67.00   0.50    0.11    --  -94.00 -77.00 120.53  176
 63  ω   -100.00 -75.00   0.50    0.11    -- -102.00 -77.00 -16.38   50
 64  ω   -140.00-115.00   0.50    0.11    -- -102.00 -77.00 -16.38   50
 65  ω   -175.00-106.00   0.50    0.11    -- -102.00 -77.00-120.00  138
 66  ω   -171.00-114.00   0.50    0.11    -- -102.00 -77.00-138.05  114
 67  ω   -111.00 -77.00   0.50    0.11    -- -102.00 -77.00-138.05   68
 68  ω    -83.00 -57.00   0.50    0.11    --  -82.00 -76.00-138.78   52
 69  ω    -76.00 -51.00   0.50    0.11    --  -78.00 -76.00-116.90   50
 70  ω    -69.00 -44.00   0.50    0.05    --  -70.00 -75.00-103.21   50
 71  ω   -160.00 -77.00   0.50    0.11    -- -102.00 -76.00-173.13  166
 72  ω   -130.00-104.00   0.50    0.05    --  -70.00 -75.00-103.21   52
 73  ω   -167.00 -73.00   0.50    0.11    --  -98.00 -76.00  39.23  188
 74  ω    -77.00 -52.00   0.50    0.11    --  -78.00 -75.00 -37.43   50
 75  ω    -86.00 -60.00   0.50    0.11    --  -86.00 -75.00 -54.30   52
 76  ω   -163.00 -68.00   0.50    0.11    --  -94.00 -75.00 -95.67  190
 77  ω   -150.00 -68.00   0.50    0.11    --  -94.00 -75.00 -64.20  164
 78  ω    -85.00 -59.00   0.50    0.11    --  -86.00 -76.00  79.68   52
 79  ω    -82.00 -48.00   0.50    0.11    --  -74.00 -74.00 100.86   68
 80  ω   -137.00 -64.00   0.50    0.11    --  -90.00 -74.00 134.33  146
 81  ω   -144.00-118.00   0.50    0.11    --  -74.00 -75.00 138.90   52
 82  ω    -87.00 -61.00   0.50    0.11    --  -86.00 -74.00 177.64   52
 83  ω    -75.00 -49.00   0.50    0.11    --  -74.00 -75.00 138.90   52
 84  ω    -78.00 -46.00   0.50    0.05    --  -70.00 -70.00  70.54   64
 85  ω    -86.00 -60.00   0.50    0.11    --  -86.00 -74.00  33.60   52
 86  ω    -88.00 -61.00   0.50    0.11    --  -86.00 -73.00  -7.64   54
 87  ω   -155.00-119.00   0.50    0.11    --  -94.00 -69.00  55.30   72
 88  ω   -154.00-128.00   0.50    0.11    --  -86.00 -73.00  -7.64   52
 89  ω    -95.00 -70.00   0.50    0.11    --  -94.00 -69.00  55.30   50
 90  ω   -149.00-110.00   0.50    0.11    --  -90.00 -66.00 143.45   78
 91  ω   -124.00 -71.00   0.50    0.11    --  -94.00 -66.00  62.21  106
 92  ω   -102.00 -67.00   0.50    0.11    --  -90.00 -66.00 143.45   70
 93  ω   -175.00 -87.00   0.50    0.11    -- -102.00 -64.00  96.38  176
 94  ω   -137.00 -72.00   0.50    0.11    --  -94.00 -67.00  11.94  130
 95  ω    -91.00 -65.00   0.50    0.11    --  -90.00 -71.00-148.97   52
 96  ω   -109.00 -67.00   0.50    0.11    --  -90.00 -69.00-121.64   84
 97  ω    -69.00 -29.00   0.50    0.11    -- -102.00  61.00 -90.00   80
 98  ω    -91.00 -33.00   0.50    0.11    -- -102.00 125.00-120.00  116
 99  ω   -104.00 -56.00   0.50    0.11    -- -102.00 125.00   0.00   96
100  ω   -117.00 -69.00   0.50    0.11    -- -102.00 125.00  90.00   96
101  ω    -63.00 -37.00   0.50    0.11    -- -102.00 125.00  90.00   52
102  ω   -116.00 -30.00   0.50    0.11    -- -102.00 125.00 120.00  172
103  ω    -82.00 -51.00   0.50    0.11    -- -102.00  90.00-170.00   62
104  ω    -66.00  29.00   0.50    0.05    --  -44.45  90.00-170.00  190
;
_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      0.0699030000
_diffrn_orient_matrix_UB_12      -0.1018921000
_diffrn_orient_matrix_UB_13      -0.0771150000
_diffrn_orient_matrix_UB_21      -0.0821552000
_diffrn_orient_matrix_UB_22      -0.0760505000
_diffrn_orient_matrix_UB_23      0.0861627000
_diffrn_orient_matrix_UB_31      -0.1053409000
_diffrn_orient_matrix_UB_32      0.0386798000
_diffrn_orient_matrix_UB_33      -0.0530932000
_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                5762
_reflns_number_total             6332
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (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 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0045(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         6332
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.106
_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)+(0.0655P)²+0.6206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1450
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 C13, C3, C19, C16, C14, C5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C13) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C5) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.2
4.a Ternary CH refined with riding coordinates:
 C4(H4), C33(H33)
4.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
4.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C28(H28), C30(H30), C32(H32), C9(H9), C19(H19), C5(H5), C21(H21),
 C11(H11), C23(H23), C3(H3), C25(H25), C13(H13), C27(H27), C7(H7), C29(H29),
 C15(H15), C31(H31), C2(H2)
;
_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
Cl1 Cl -0.07141(12) 0.21660(9) 0.68276(9) 0.1191(3) Uani 1 1 d . . . . .
Cl3 Cl -0.13355(9) 0.45269(8) 0.60959(14) 0.1588(6) Uani 1 1 d . . . . .
Cl2 Cl -0.00762(14) 0.27500(12) 0.45490(9) 0.1434(5) Uani 1 1 d . . . . .
O1 O 0.28152(12) 0.28575(13) 0.49718(12) 0.0565(3) Uani 1 1 d . . . . .
O4 O 0.20617(14) 0.21477(11) 0.75509(12) 0.0584(4) Uani 1 1 d . . . . .
O6 O 0.40155(15) 0.43462(13) 0.81878(11) 0.0606(4) Uani 1 1 d . . . . .
O7 O 0.51812(15) 0.56183(13) 0.72253(12) 0.0642(4) Uani 1 1 d . . . . .
O2 O 0.25693(15) 0.58079(13) 0.64645(13) 0.0636(4) Uani 1 1 d . . . . .
O5 O 0.32381(15) 0.08087(13) 0.23475(13) 0.0651(4) Uani 1 1 d . . . . .
O3 O 0.45500(17) -0.09145(13) 0.17357(14) 0.0707(4) Uani 1 1 d . . . . .
N1 N 0.25670(14) 0.38754(13) 0.67995(12) 0.0460(3) Uani 1 1 d . . . . .
N2 N 0.37629(13) 0.34095(13) 0.60167(12) 0.0463(3) Uani 1 1 d . . . . .
C1 C 0.37523(16) 0.27581(15) 0.52249(14) 0.0433(4) Uani 1 1 d . . . . .
C4 C 0.49296(16) 0.29821(16) 0.63307(14) 0.0440(4) Uani 1 1 d . . . . .
H4 H 0.4690 0.2585 0.7061 0.053 Uiso 1 1 calc R U . . .
C6 C 0.50762(15) 0.19682(15) 0.48411(14) 0.0411(4) Uani 1 1 d . . . . .
C8 C 0.57653(16) 0.21099(15) 0.54645(14) 0.0438(4) Uani 1 1 d . . . . .
C10 C 0.17736(17) 0.31883(15) 0.75309(14) 0.0445(4) Uani 1 1 d . . . . .
C12 C 0.55908(17) 0.11240(15) 0.40516(14) 0.0447(4) Uani 1 1 d . . . . .
C14 C 0.07495(18) 0.51240(16) 0.78742(15) 0.0480(4) Uani 1 1 d . U . . .
C16 C 0.05957(17) 0.40150(16) 0.82029(14) 0.0465(4) Uani 1 1 d . U . . .
C18 C 0.55479(18) 0.39333(18) 0.63460(16) 0.0512(4) Uani 1 1 d . . . . .
H18A H 0.6440 0.3594 0.6312 0.061 Uiso 1 1 calc R U . . .
H18B H 0.5581 0.4442 0.5696 0.061 Uiso 1 1 calc R U . . .
C20 C 0.48104(18) 0.46292(16) 0.73603(15) 0.0480(4) Uani 1 1 d . . . . .
C22 C 0.48135(18) 0.09685(16) 0.34382(15) 0.0486(4) Uani 1 1 d . . . . .
H22 H 0.4049 0.1533 0.3488 0.058 Uiso 1 1 calc R U . . .
C24 C 0.20365(18) 0.50632(15) 0.69627(15) 0.0471(4) Uani 1 1 d . . . . .
C26 C 0.4315(2) -0.00810(17) 0.22366(15) 0.0518(4) Uani 1 1 d . . . . .
C28 C 0.5119(2) 0.00859(17) 0.28205(16) 0.0527(4) Uani 1 1 d . . . . .
H28 H 0.5896 -0.0468 0.2751 0.063 Uiso 1 1 calc R U . . .
C30 C 0.70228(17) 0.14498(18) 0.52964(17) 0.0533(5) Uani 1 1 d . . . . .
H30 H 0.7501 0.1564 0.5692 0.064 Uiso 1 1 calc R U . . .
C32 C 0.68521(18) 0.04445(18) 0.39136(17) 0.0550(5) Uani 1 1 d . . . . .
H32 H 0.7232 -0.0131 0.3404 0.066 Uiso 1 1 calc R U . . .
C34 C 0.4611(2) 0.63303(18) 0.81413(17) 0.0567(5) Uani 1 1 d . . . . .
C17 C 0.2469(2) 0.07768(17) 0.17416(17) 0.0555(5) Uani 1 1 d . . . . .
C9 C 0.75482(19) 0.06100(19) 0.45182(19) 0.0597(5) Uani 1 1 d . . . . .
H9 H 0.8388 0.0148 0.4400 0.072 Uiso 1 1 calc R U . . .
C19 C -0.0515(2) 0.3807(2) 0.90357(17) 0.0602(5) Uani 1 1 d . U . . .
H19 H -0.0613 0.3060 0.9249 0.072 Uiso 1 1 calc R U . . .
C5 C -0.0208(2) 0.60662(19) 0.83805(19) 0.0641(5) Uani 1 1 d . U . . .
H5 H -0.0114 0.6814 0.8167 0.077 Uiso 1 1 calc R U . . .
C21 C 0.2923(2) 0.09795(19) 0.06189(19) 0.0652(5) Uani 1 1 d . . . . .
H21 H 0.3759 0.1094 0.0251 0.078 Uiso 1 1 calc R U . . .
C11 C 0.3458(2) 0.71360(19) 0.82616(19) 0.0628(5) Uani 1 1 d . . . . .
H11 H 0.3019 0.7183 0.7781 0.075 Uiso 1 1 calc R U . . .
C23 C 0.2963(3) 0.7879(2) 0.9116(2) 0.0753(7) Uani 1 1 d . . . . .
H23 H 0.2186 0.8441 0.9206 0.090 Uiso 1 1 calc R U . . .
C3 C -0.1478(2) 0.4755(2) 0.95415(19) 0.0710(6) Uani 1 1 d . U . . .
H3 H -0.2241 0.4645 1.0104 0.085 Uiso 1 1 calc R U . . .
C25 C 0.2126(3) 0.1012(2) 0.0045(2) 0.0795(7) Uani 1 1 d . . . . .
H25 H 0.2422 0.1154 -0.0716 0.095 Uiso 1 1 calc R U . . .
C13 C -0.1323(2) 0.5850(2) 0.9225(2) 0.0739(7) Uani 1 1 d . U . . .
H13 H -0.1982 0.6469 0.9585 0.089 Uiso 1 1 calc R U . . .
C27 C 0.1243(3) 0.0608(2) 0.2297(2) 0.0733(6) Uani 1 1 d . . . . .
H27 H 0.0942 0.0477 0.3059 0.088 Uiso 1 1 calc R U . . .
C7 C 0.3597(3) 0.7802(2) 0.9832(2) 0.0818(8) Uani 1 1 d . . . . .
H7 H 0.3252 0.8306 1.0405 0.098 Uiso 1 1 calc R U . . .
C29 C 0.0908(3) 0.0836(2) 0.0582(3) 0.0871(8) Uani 1 1 d . . . . .
H29 H 0.0378 0.0851 0.0187 0.104 Uiso 1 1 calc R U . . .
C15 C 0.5263(3) 0.6237(2) 0.8843(2) 0.0801(7) Uani 1 1 d . . . . .
H15 H 0.6047 0.5683 0.8747 0.096 Uiso 1 1 calc R U . . .
C31 C 0.4739(4) 0.6981(3) 0.9701(3) 0.0925(9) Uani 1 1 d . . . . .
H31 H 0.5168 0.6922 1.0191 0.111 Uiso 1 1 calc R U . . .
C2 C 0.0461(3) 0.0636(3) 0.1705(3) 0.0904(8) Uani 1 1 d . . . . .
H2 H -0.0374 0.0519 0.2070 0.109 Uiso 1 1 calc R U . . .
C33 C -0.0228(3) 0.3200(3) 0.5794(3) 0.0836(8) Uani 1 1 d . . . . .
H33 H 0.0628 0.3270 0.5744 0.100 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 C33 1.740(3) . ?
Cl3 C33 1.730(3) . ?
Cl2 C33 1.727(3) . ?
O1 C1 1.206(2) . ?
O4 C10 1.207(2) . ?
O6 C20 1.197(2) . ?
O7 C20 1.344(2) . ?
O7 C34 1.414(2) . ?
O2 C24 1.200(2) . ?
O5 C26 1.361(2) . ?
O5 C17 1.401(2) . ?
O3 C26 1.195(2) . ?
N1 N2 1.3784(19) . ?
N1 C10 1.399(2) . ?
N1 C24 1.406(2) . ?
N2 C1 1.398(2) . ?
N2 C4 1.475(2) . ?
C1 C6 1.481(2) . ?
C4 H4 0.9800 . ?
C4 C8 1.507(2) . ?
C4 C18 1.515(2) . ?
C6 C8 1.387(2) . ?
C6 C12 1.403(2) . ?
C8 C30 1.382(3) . ?
C10 C16 1.476(2) . ?
C12 C22 1.467(3) . ?
C12 C32 1.399(3) . ?
C14 C16 1.386(3) . ?
C14 C24 1.488(3) . ?
C14 C5 1.378(3) . ?
C16 C19 1.380(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C20 1.503(2) . ?
C22 H22 0.9300 . ?
C22 C28 1.321(3) . ?
C26 C28 1.467(3) . ?
C28 H28 0.9300 . ?
C30 H30 0.9300 . ?
C30 C9 1.388(3) . ?
C32 H32 0.9300 . ?
C32 C9 1.384(3) . ?
C34 C11 1.367(3) . ?
C34 C15 1.363(3) . ?
C17 C21 1.371(3) . ?
C17 C27 1.366(3) . ?
C9 H9 0.9300 . ?
C19 H19 0.9300 . ?
C19 C3 1.385(3) . ?
C5 H5 0.9300 . ?
C5 C13 1.393(3) . ?
C21 H21 0.9300 . ?
C21 C25 1.374(4) . ?
C11 H11 0.9300 . ?
C11 C23 1.382(3) . ?
C23 H23 0.9300 . ?
C23 C7 1.366(4) . ?
C3 H3 0.9300 . ?
C3 C13 1.368(4) . ?
C25 H25 0.9300 . ?
C25 C29 1.359(4) . ?
C13 H13 0.9300 . ?
C27 H27 0.9300 . ?
C27 C2 1.379(4) . ?
C7 H7 0.9300 . ?
C7 C31 1.364(4) . ?
C29 H29 0.9300 . ?
C29 C2 1.371(5) . ?
C15 H15 0.9300 . ?
C15 C31 1.383(4) . ?
C31 H31 0.9300 . ?
C2 H2 0.9300 . ?
C33 H33 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 O7 C34 116.62(15) . . ?
C26 O5 C17 116.99(15) . . ?
N2 N1 C10 122.19(14) . . ?
N2 N1 C24 124.29(15) . . ?
C10 N1 C24 113.51(14) . . ?
N1 N2 C1 116.54(14) . . ?
N1 N2 C4 119.82(14) . . ?
C1 N2 C4 113.68(13) . . ?
O1 C1 N2 124.10(16) . . ?
O1 C1 C6 130.99(16) . . ?
N2 C1 C6 104.90(14) . . ?
N2 C4 H4 109.4 . . ?
N2 C4 C8 100.56(13) . . ?
N2 C4 C18 112.91(15) . . ?
C8 C4 H4 109.4 . . ?
C8 C4 C18 114.80(14) . . ?
C18 C4 H4 109.4 . . ?
C8 C6 C1 108.92(14) . . ?
C8 C6 C12 122.10(16) . . ?
C12 C6 C1 128.79(16) . . ?
C6 C8 C4 110.92(15) . . ?
C30 C8 C4 128.10(16) . . ?
C30 C8 C6 120.87(16) . . ?
O4 C10 N1 124.17(16) . . ?
O4 C10 C16 131.03(18) . . ?
N1 C10 C16 104.80(15) . . ?
C6 C12 C22 120.60(16) . . ?
C32 C12 C6 116.13(16) . . ?
C32 C12 C22 123.26(16) . . ?
C16 C14 C24 109.05(15) . . ?
C5 C14 C16 120.75(18) . . ?
C5 C14 C24 130.20(19) . . ?
C14 C16 C10 108.73(16) . . ?
C19 C16 C10 129.42(18) . . ?
C19 C16 C14 121.85(17) . . ?
C4 C18 H18A 109.1 . . ?
C4 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C20 C18 C4 112.57(15) . . ?
C20 C18 H18A 109.1 . . ?
C20 C18 H18B 109.1 . . ?
O6 C20 O7 123.84(17) . . ?
O6 C20 C18 125.42(17) . . ?
O7 C20 C18 110.72(16) . . ?
C12 C22 H22 117.6 . . ?
C28 C22 C12 124.85(18) . . ?
C28 C22 H22 117.6 . . ?
O2 C24 N1 125.07(17) . . ?
O2 C24 C14 131.04(17) . . ?
N1 C24 C14 103.86(15) . . ?
O5 C26 C28 112.75(16) . . ?
O3 C26 O5 122.86(19) . . ?
O3 C26 C28 124.37(19) . . ?
C22 C28 C26 124.50(19) . . ?
C22 C28 H28 117.8 . . ?
C26 C28 H28 117.8 . . ?
C8 C30 H30 121.1 . . ?
C8 C30 C9 117.78(18) . . ?
C9 C30 H30 121.1 . . ?
C12 C32 H32 119.3 . . ?
C9 C32 C12 121.49(17) . . ?
C9 C32 H32 119.3 . . ?
C11 C34 O7 119.0(2) . . ?
C15 C34 O7 119.0(2) . . ?
C15 C34 C11 121.9(2) . . ?
C21 C17 O5 119.8(2) . . ?
C27 C17 O5 118.8(2) . . ?
C27 C17 C21 121.3(2) . . ?
C30 C9 H9 119.2 . . ?
C32 C9 C30 121.57(18) . . ?
C32 C9 H9 119.2 . . ?
C16 C19 H19 121.3 . . ?
C16 C19 C3 117.3(2) . . ?
C3 C19 H19 121.3 . . ?
C14 C5 H5 121.5 . . ?
C14 C5 C13 117.1(2) . . ?
C13 C5 H5 121.5 . . ?
C17 C21 H21 120.4 . . ?
C17 C21 C25 119.1(2) . . ?
C25 C21 H21 120.4 . . ?
C34 C11 H11 120.9 . . ?
C34 C11 C23 118.2(2) . . ?
C23 C11 H11 120.9 . . ?
C11 C23 H23 119.5 . . ?
C7 C23 C11 121.0(2) . . ?
C7 C23 H23 119.5 . . ?
C19 C3 H3 119.6 . . ?
C13 C3 C19 120.9(2) . . ?
C13 C3 H3 119.6 . . ?
C21 C25 H25 119.8 . . ?
C29 C25 C21 120.4(3) . . ?
C29 C25 H25 119.8 . . ?
C5 C13 H13 119.0 . . ?
C3 C13 C5 122.08(19) . . ?
C3 C13 H13 119.0 . . ?
C17 C27 H27 120.6 . . ?
C17 C27 C2 118.8(2) . . ?
C2 C27 H27 120.6 . . ?
C23 C7 H7 120.2 . . ?
C31 C7 C23 119.7(2) . . ?
C31 C7 H7 120.2 . . ?
C25 C29 H29 120.0 . . ?
C25 C29 C2 120.1(2) . . ?
C2 C29 H29 120.0 . . ?
C34 C15 H15 120.6 . . ?
C34 C15 C31 118.8(3) . . ?
C31 C15 H15 120.6 . . ?
C7 C31 C15 120.4(3) . . ?
C7 C31 H31 119.8 . . ?
C15 C31 H31 119.8 . . ?
C27 C2 H2 119.8 . . ?
C29 C2 C27 120.3(3) . . ?
C29 C2 H2 119.8 . . ?
Cl1 C33 H33 108.7 . . ?
Cl3 C33 Cl1 110.72(17) . . ?
Cl3 C33 H33 108.7 . . ?
Cl2 C33 Cl1 109.00(16) . . ?
Cl2 C33 Cl3 110.96(18) . . ?
Cl2 C33 H33 108.7 . . ?

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
O1 C1 C6 C8 -173.9(2) . . . . ?
O1 C1 C6 C12 1.0(3) . . . . ?
O4 C10 C16 C14 178.6(2) . . . . ?
O4 C10 C16 C19 -1.2(4) . . . . ?
O7 C34 C11 C23 -175.43(19) . . . . ?
O7 C34 C15 C31 176.3(2) . . . . ?
O5 C26 C28 C22 3.3(3) . . . . ?
O5 C17 C21 C25 -176.2(2) . . . . ?
O5 C17 C27 C2 176.7(2) . . . . ?
O3 C26 C28 C22 -175.1(2) . . . . ?
N1 N2 C1 O1 23.3(3) . . . . ?
N1 N2 C1 C6 -155.42(15) . . . . ?
N1 N2 C4 C8 154.80(15) . . . . ?
N1 N2 C4 C18 -82.4(2) . . . . ?
N1 C10 C16 C14 -1.6(2) . . . . ?
N1 C10 C16 C19 178.6(2) . . . . ?
N2 N1 C10 O4 0.7(3) . . . . ?
N2 N1 C10 C16 -179.02(15) . . . . ?
N2 N1 C24 O2 -2.0(3) . . . . ?
N2 N1 C24 C14 179.37(15) . . . . ?
N2 C1 C6 C8 4.73(19) . . . . ?
N2 C1 C6 C12 179.68(17) . . . . ?
N2 C4 C8 C6 -6.91(19) . . . . ?
N2 C4 C8 C30 176.89(19) . . . . ?
N2 C4 C18 C20 77.5(2) . . . . ?
C1 N2 C4 C8 10.34(19) . . . . ?
C1 N2 C4 C18 133.16(16) . . . . ?
C1 C6 C8 C4 1.7(2) . . . . ?
C1 C6 C8 C30 178.18(17) . . . . ?
C1 C6 C12 C22 3.2(3) . . . . ?
C1 C6 C12 C32 -175.48(18) . . . . ?
C4 N2 C1 O1 169.03(18) . . . . ?
C4 N2 C1 C6 -9.7(2) . . . . ?
C4 C8 C30 C9 173.18(19) . . . . ?
C4 C18 C20 O6 16.3(3) . . . . ?
C4 C18 C20 O7 -164.88(16) . . . . ?
C6 C8 C30 C9 -2.7(3) . . . . ?
C6 C12 C22 C28 -168.20(19) . . . . ?
C6 C12 C32 C9 -0.6(3) . . . . ?
C8 C4 C18 C20 -167.98(16) . . . . ?
C8 C6 C12 C22 177.57(17) . . . . ?
C8 C6 C12 C32 -1.1(3) . . . . ?
C8 C30 C9 C32 1.0(3) . . . . ?
C10 N1 N2 C1 61.4(2) . . . . ?
C10 N1 N2 C4 -82.1(2) . . . . ?
C10 N1 C24 O2 176.68(18) . . . . ?
C10 N1 C24 C14 -1.9(2) . . . . ?
C10 C16 C19 C3 179.4(2) . . . . ?
C12 C6 C8 C4 -173.69(16) . . . . ?
C12 C6 C8 C30 2.8(3) . . . . ?
C12 C22 C28 C26 178.04(18) . . . . ?
C12 C32 C9 C30 0.6(3) . . . . ?
C14 C16 C19 C3 -0.4(3) . . . . ?
C14 C5 C13 C3 -0.5(4) . . . . ?
C16 C14 C24 O2 -177.7(2) . . . . ?
C16 C14 C24 N1 0.8(2) . . . . ?
C16 C14 C5 C13 -0.1(3) . . . . ?
C16 C19 C3 C13 -0.3(4) . . . . ?
C18 C4 C8 C6 -128.41(17) . . . . ?
C18 C4 C8 C30 55.4(3) . . . . ?
C20 O7 C34 C11 -88.9(2) . . . . ?
C20 O7 C34 C15 94.8(3) . . . . ?
C22 C12 C32 C9 -179.2(2) . . . . ?
C24 N1 N2 C1 -120.04(19) . . . . ?
C24 N1 N2 C4 96.5(2) . . . . ?
C24 N1 C10 O4 -177.98(18) . . . . ?
C24 N1 C10 C16 2.3(2) . . . . ?
C24 C14 C16 C10 0.5(2) . . . . ?
C24 C14 C16 C19 -179.69(18) . . . . ?
C24 C14 C5 C13 -179.8(2) . . . . ?
C26 O5 C17 C21 -72.1(3) . . . . ?
C26 O5 C17 C27 111.7(2) . . . . ?
C32 C12 C22 C28 10.4(3) . . . . ?
C34 O7 C20 O6 2.0(3) . . . . ?
C34 O7 C20 C18 -176.87(18) . . . . ?
C34 C11 C23 C7 -0.9(4) . . . . ?
C34 C15 C31 C7 -0.8(5) . . . . ?
C17 O5 C26 O3 -7.0(3) . . . . ?
C17 O5 C26 C28 174.64(18) . . . . ?
C17 C21 C25 C29 -0.5(4) . . . . ?
C17 C27 C2 C29 -0.4(4) . . . . ?
C19 C3 C13 C5 0.7(4) . . . . ?
C5 C14 C16 C10 -179.23(18) . . . . ?
C5 C14 C16 C19 0.6(3) . . . . ?
C5 C14 C24 O2 2.0(4) . . . . ?
C5 C14 C24 N1 -179.5(2) . . . . ?
C21 C17 C27 C2 0.5(4) . . . . ?
C21 C25 C29 C2 0.6(4) . . . . ?
C11 C34 C15 C31 0.0(4) . . . . ?
C11 C23 C7 C31 0.2(4) . . . . ?
C23 C7 C31 C15 0.6(5) . . . . ?
C25 C29 C2 C27 -0.2(5) . . . . ?
C27 C17 C21 C25 -0.1(3) . . . . ?
C15 C34 C11 C23 0.8(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 2.065
_oxdiff_exptl_absorpt_empirical_full_min 0.739
