# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_tx4035
_database_code_depnum_ccdc_archive 'CCDC 2211975'
loop_
_audit_author_name
_audit_author_address
'Song Ye'
;Institute of Chemistry, CAS
China
;
_audit_update_record             
;
2022-10-10 deposited with the CCDC.	2022-12-20 downloaded from the CCDC.
;
_audit_creation_date             2020-12-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 I O2'
_chemical_formula_sum            'C13 H13 I O2'
_chemical_formula_weight         328.13
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHOI
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'
I I -0.3257 6.8362 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.72921(5)
_cell_length_b                   19.8664(2)
_cell_length_c                   16.68090(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.5198(8)
_cell_angle_gamma                90
_cell_volume                     1896.76(3)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    27834
_cell_measurement_temperature    169.99(11)
_cell_measurement_theta_max      74.8080
_cell_measurement_theta_min      2.6490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    19.766
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33429
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.300
_diffrn_reflns_theta_min         2.651
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -109.00 -75.00   0.50    0.05    --  -47.20 -10.00  -1.00   68
  2  ω    -21.00   4.00   0.50    0.05    --  -47.20  10.00 171.00   50
  3  ω    -12.00  14.00   0.50    0.05    --   47.20 -10.00  -1.00   52
  4  ω     31.00  89.00   0.50    0.05    --   47.20  10.00 171.00  116
  5  ω   -131.00 -85.00   0.50    0.10    --  -99.00 -10.00  -1.00   92
  6  ω    126.00 168.00   0.50    0.10    --  103.25  10.00 171.00   84
  7  ω    -89.00 -13.00   0.50    0.05    --  -47.20 125.00-120.00  152
  8  ω    -53.00 -27.00   0.50    0.05    --  -47.20 -77.00-120.00   52
  9  ω     25.00  51.00   0.50    0.05    --   47.20  77.00-120.00   52
 10  ω     35.00  92.00   0.50    0.05    --   47.20  19.00 -90.00  114
 11  ω     36.00  63.00   0.50    0.05    --   47.20  38.00 -90.00   54
 12  ω     33.00  60.00   0.50    0.05    --   47.20  57.00 -90.00   54
 13  ω     32.00  85.00   0.50    0.05    --   47.20  77.00-180.00  106
 14  ω     35.00  87.00   0.50    0.05    --   47.20  38.00 -30.00  104
 15  ω     34.00  61.00   0.50    0.05    --   47.20  57.00-120.00   54
 16  ω     28.00  55.00   0.50    0.05    --   47.20  77.00 -90.00   54
 17  ω     34.00 106.00   0.50    0.05    --   47.20  77.00 -60.00  144
 18  ω     33.00  65.00   0.50    0.05    --   47.20  57.00 -60.00   64
 19  ω     28.00  54.00   0.50    0.05    --   47.20  77.00  60.00   52
 20  ω    -68.00 -29.00   0.50    0.10    --  -99.00  61.00  90.00   78
 21  ω   -128.00 -78.00   0.50    0.10    --  -99.00 -78.00 -12.48  100
 22  ω   -160.00 -78.00   0.50    0.10    --  -99.00 -72.00 -37.34  164
 23  ω   -101.00 -75.00   0.50    0.10    --  -99.00 -80.00 -40.13   52
 24  ω   -103.00 -78.00   0.50    0.10    --  -99.00 -73.00-146.80   50
 25  ω   -108.00 -82.00   0.50    0.10    --  -99.00 -61.00 -60.00   52
 26  ω   -168.00-116.00   0.50    0.10    --  -99.00 -73.00-146.80  104
 27  ω   -101.00 -76.00   0.50    0.10    --  -99.00 -77.00-120.00   50
 28  ω   -109.00 -83.00   0.50    0.10    --  -99.00 -61.00 -90.00   52
 29  ω   -110.00 -80.00   0.50    0.10    --  -99.00 -68.00-118.64   60
 30  ω   -108.00 -82.00   0.50    0.10    --  -99.00 -63.00-119.57   52
 31  ω   -105.00 -76.00   0.50    0.10    --  -99.00 -77.00   0.00   58
 32  ω   -160.00 -77.00   0.50    0.10    --  -99.00 -76.00 -23.15  166
 33  ω   -168.00 -79.00   0.50    0.10    --  -99.00 -70.00 -94.44  178
 34  ω   -106.00 -80.00   0.50    0.10    --  -99.00 -77.00 -90.00   52
 35  ω   -167.00-108.00   0.50    0.10    --  -99.00 -80.00 -43.07  118
 36  ω   -101.00 -75.00   0.50    0.10    --  -99.00 -80.00 -43.07   52
 37  ω   -159.00-132.00   0.50    0.10    --  -99.00 -61.00 -90.00   54
 38  ω   -105.00 -77.00   0.50    0.10    --  -99.00 -74.00   8.53   56
 39  ω   -110.00 -82.00   0.50    0.10    --  -99.00 -61.00-150.00   56
 40  ω   -164.00-138.00   0.50    0.10    --  -99.00 -68.00-118.64   52
 41  ω   -102.00 -76.00   0.50    0.10    --  -99.00 -77.00-150.00   52
 42  ω   -102.00 -76.00   0.50    0.10    --  -99.00 -78.00 -53.27   52
 43  ω   -103.00 -77.00   0.50    0.10    --  -99.00 -77.00 -60.00   52
 44  ω   -118.00 -79.00   0.50    0.10    --  -99.00 -69.00-135.46   78
 45  ω   -167.00-141.00   0.50    0.10    --  -99.00 -78.00 -53.27   52
 46  ω   -168.00-142.00   0.50    0.10    --  -99.00 -77.00 -60.00   52
 47  ω   -166.00-140.00   0.50    0.10    --  -99.00 -75.00  -7.52   52
 48  ω   -102.00 -77.00   0.50    0.10    --  -99.00 -75.00  -7.52   50
 49  ω   -160.00-135.00   0.50    0.10    --  -99.00 -47.00 -99.60   50
 50  ω   -129.00 -90.00   0.50    0.10    --  -99.00 -47.00 -99.60   78
 51  ω   -165.00-140.00   0.50    0.10    --  -99.00 -55.00-162.71   50
 52  ω   -111.00 -85.00   0.50    0.10    --  -99.00 -55.00-162.71   52
 53  ω   -114.00 -85.00   0.50    0.10    --  -99.00 -51.00 -65.47   58
 54  ω   -167.00-142.00   0.50    0.10    --  -99.00 -51.00 -65.47   50
 55  ω   -168.00 -92.00   0.50    0.10    --  -99.00 -45.00-129.43  152
 56  ω   -108.00 -82.00   0.50    0.10    --  -99.00 -64.00-169.83   52
 57  ω   -165.00-139.00   0.50    0.10    --  -99.00 -77.00-150.00   52
 58  ω   -102.00 -76.00   0.50    0.10    --  -99.00 -78.00  -9.26   52
 59  ω   -108.00 -82.00   0.50    0.10    --  -99.00 -61.00-120.00   52
 60  ω   -105.00 -79.00   0.50    0.10    --  -99.00 -71.00 -87.14   52
 61  ω     31.00  96.00   0.50    0.10    --  103.25 -94.00-120.00  130
 62  ω     54.00  89.00   0.50    0.10    --  103.25 -94.00 -30.00   70
 63  ω     81.00 107.00   0.50    0.10    --  103.25  77.00-150.00   52
 64  ω     31.00  74.00   0.50    0.10    --  103.25 -61.00 -90.00   86
 65  ω     33.00 103.00   0.50    0.10    --  103.25 -94.00-150.00  140
 66  ω     31.00  75.00   0.50    0.10    --  103.25 -61.00 120.00   88
 67  ω     32.00 105.00   0.50    0.10    --  103.25 -94.00 -90.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1974752000
_diffrn_orient_matrix_UB_12      0.0009590000
_diffrn_orient_matrix_UB_13      0.0657338000
_diffrn_orient_matrix_UB_21      -0.1815013000
_diffrn_orient_matrix_UB_22      0.0105810000
_diffrn_orient_matrix_UB_23      0.0642896000
_diffrn_orient_matrix_UB_31      -0.0227670000
_diffrn_orient_matrix_UB_32      -0.0767985000
_diffrn_orient_matrix_UB_33      0.0096899000
_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              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.864
_reflns_number_gt                7004
_reflns_number_total             7200
_reflns_odcompleteness_completeness 100.00
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.798
_refine_diff_density_min         -1.594
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details 
;
 Flack x determined using 3077 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.064
_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)+(0.0820P)²+1.0193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1092
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C1A(H1A), C1B(H1B)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C4A(H4AA,H4AB), C5A(H5AA,
 H5AB), C6A(H6AA,H6AB), C7A(H7AA,H7AB), C4B(H4BA,H4BB), C5B(H5BA,H5BB),
 C6B(H6BA,H6BB), C7B(H7BA,H7BB)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C9A(H9A), C10A(H10A), C12A(H12A),
 C13A(H13A), C9B(H9B), C10B(H10B), C12B(H12B), C13B(H13B)
;
_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
I1 I 0.64970(9) 0.33016(3) 0.83104(3) 0.04233(15) Uani 1 1 d . . . . .
O1 O 0.5203(9) 0.6596(3) 0.9966(3) 0.0329(11) Uani 1 1 d . . . . .
O2 O 0.2998(10) 0.6736(4) 0.8807(4) 0.0447(14) Uani 1 1 d . . . . .
C1 C 0.7371(12) 0.6856(4) 0.9007(4) 0.0286(14) Uani 1 1 d . . . . .
H1 H 0.808151 0.655527 0.862131 0.034 Uiso 1 1 calc R U . . .
C2 C 0.7822(12) 0.6679(4) 0.9894(4) 0.0300(14) Uani 1 1 d . . . . .
C3 C 0.4854(12) 0.6724(4) 0.9163(4) 0.0290(14) Uani 1 1 d . . . . .
C4 C 0.7948(15) 0.7609(4) 0.8924(5) 0.0407(17) Uani 1 1 d . . . . .
H4A H 0.953042 0.767102 0.875336 0.049 Uiso 1 1 calc R U . . .
H4B H 0.687198 0.782496 0.853912 0.049 Uiso 1 1 calc R U . . .
C5 C 0.7674(18) 0.7892(5) 0.9766(6) 0.050(2) Uani 1 1 d . . . . .
H5A H 0.604929 0.798767 0.986118 0.060 Uiso 1 1 calc R U . . .
H5B H 0.858462 0.829950 0.984813 0.060 Uiso 1 1 calc R U . . .
C6 C 0.8612(15) 0.7321(5) 1.0314(5) 0.0415(18) Uani 1 1 d . . . . .
H6A H 1.030289 0.733839 1.037366 0.050 Uiso 1 1 calc R U . . .
H6B H 0.796803 0.735135 1.084113 0.050 Uiso 1 1 calc R U . . .
C7 C 0.9062(12) 0.6045(4) 1.0162(4) 0.0305(15) Uani 1 1 d . . . . .
H7A H 0.876522 0.597100 1.072308 0.037 Uiso 1 1 calc R U . . .
H7B H 1.072918 0.611576 1.012455 0.037 Uiso 1 1 calc R U . . .
C8 C 0.8397(11) 0.5413(4) 0.9701(4) 0.0249(13) Uani 1 1 d . . . . .
C9 C 0.6313(12) 0.5073(4) 0.9833(4) 0.0307(14) Uani 1 1 d . . . . .
H9 H 0.527347 0.525019 1.019006 0.037 Uiso 1 1 calc R U . . .
C10 C 0.5776(12) 0.4474(4) 0.9435(4) 0.0300(14) Uani 1 1 d . . . . .
H10 H 0.439080 0.424945 0.953051 0.036 Uiso 1 1 calc R U . . .
C11 C 0.7310(13) 0.4212(4) 0.8899(4) 0.0303(14) Uani 1 1 d . . . . .
C12 C 0.9375(13) 0.4549(4) 0.8750(4) 0.0338(15) Uani 1 1 d . . . . .
H12 H 1.039362 0.437718 0.838277 0.041 Uiso 1 1 calc R U . . .
C13 C 0.9895(11) 0.5136(4) 0.9151(4) 0.0303(14) Uani 1 1 d . . . . .
H13 H 1.128612 0.535655 0.905302 0.036 Uiso 1 1 calc R U . . .
I1A I 0.42537(9) 0.62024(3) 0.18566(3) 0.04098(15) Uani 1 1 d . . . . .
O1A O 0.7563(8) 0.5358(3) 0.5869(3) 0.0337(11) Uani 1 1 d . . . . .
O2A O 0.9963(9) 0.4875(4) 0.6832(4) 0.0487(16) Uani 1 1 d . . . . .
C1A C 0.5574(10) 0.4999(3) 0.6831(4) 0.0245(12) Uani 1 1 d . . . . .
H1A H 0.495013 0.454692 0.692108 0.029 Uiso 1 1 calc R U . . .
C2A C 0.4976(10) 0.5314(3) 0.5997(4) 0.0227(12) Uani 1 1 d . . . . .
C3A C 0.8056(12) 0.5032(4) 0.6572(4) 0.0336(16) Uani 1 1 d . . . . .
C4A C 0.4998(13) 0.5532(4) 0.7451(4) 0.0314(14) Uani 1 1 d . . . . .
H4AA H 0.614561 0.552994 0.789632 0.038 Uiso 1 1 calc R U . . .
H4AB H 0.346258 0.545517 0.765634 0.038 Uiso 1 1 calc R U . . .
C5A C 0.5064(16) 0.6201(4) 0.6991(4) 0.0398(16) Uani 1 1 d . . . . .
H5AA H 0.665258 0.636585 0.696126 0.048 Uiso 1 1 calc R U . . .
H5AB H 0.412517 0.654155 0.724184 0.048 Uiso 1 1 calc R U . . .
C6A C 0.4029(13) 0.6014(3) 0.6155(4) 0.0297(14) Uani 1 1 d . . . . .
H6AA H 0.233528 0.600999 0.615026 0.036 Uiso 1 1 calc R U . . .
H6AB H 0.452542 0.633083 0.575392 0.036 Uiso 1 1 calc R U . . .
C7A C 0.3799(11) 0.4892(3) 0.5348(4) 0.0253(12) Uani 1 1 d . . . . .
H7AA H 0.217454 0.482983 0.547162 0.030 Uiso 1 1 calc R U . . .
H7AB H 0.453042 0.445141 0.534932 0.030 Uiso 1 1 calc R U . . .
C8A C 0.3904(10) 0.5191(3) 0.4517(4) 0.0232(12) Uani 1 1 d . . . . .
C9A C 0.5816(11) 0.5084(4) 0.4051(4) 0.0313(14) Uani 1 1 d . . . . .
H9A H 0.703990 0.481684 0.425154 0.038 Uiso 1 1 calc R U . . .
C10A C 0.5944(12) 0.5365(4) 0.3298(4) 0.0313(15) Uani 1 1 d . . . . .
H10A H 0.723712 0.528579 0.299359 0.038 Uiso 1 1 calc R U . . .
C11A C 0.4114(12) 0.5768(4) 0.3000(4) 0.0274(13) Uani 1 1 d . . . . .
C12A C 0.2178(13) 0.5880(5) 0.3448(4) 0.0352(15) Uani 1 1 d . . . . .
H12A H 0.094824 0.614368 0.324487 0.042 Uiso 1 1 calc R U . . .
C13A C 0.2095(12) 0.5592(4) 0.4207(4) 0.0332(15) Uani 1 1 d . . . . .
H13A H 0.080273 0.566910 0.451206 0.040 Uiso 1 1 calc R U . . .
I1B I 0.8486(2) 0.42691(4) 0.15410(4) 0.0842(3) Uani 1 1 d . . . . .
O1B O 0.8565(9) 0.2444(3) 0.5195(3) 0.0362(11) Uani 1 1 d . . . . .
O2B O 0.6410(10) 0.3362(4) 0.5496(5) 0.0577(17) Uani 1 1 d . . . . .
C1B C 1.0788(11) 0.3256(4) 0.5587(4) 0.0284(13) Uani 1 1 d . . . . .
H1B H 1.138905 0.362857 0.527070 0.034 Uiso 1 1 calc R U . . .
C2B C 1.1202(11) 0.2543(4) 0.5263(4) 0.0289(13) Uani 1 1 d . . . . .
C3B C 0.8252(12) 0.3086(4) 0.5441(5) 0.0346(16) Uani 1 1 d . . . . .
C4B C 1.1548(14) 0.3243(5) 0.6477(5) 0.0415(17) Uani 1 1 d . . . . .
H4BA H 1.049860 0.350834 0.679003 0.050 Uiso 1 1 calc R U . . .
H4BB H 1.312323 0.341574 0.656030 0.050 Uiso 1 1 calc R U . . .
C5B C 1.1433(16) 0.2496(5) 0.6707(5) 0.0447(19) Uani 1 1 d . . . . .
H5BA H 1.246592 0.239887 0.716841 0.054 Uiso 1 1 calc R U . . .
H5BB H 0.985321 0.236635 0.682666 0.054 Uiso 1 1 calc R U . . .
C6B C 1.2236(14) 0.2130(4) 0.5957(5) 0.0358(16) Uani 1 1 d . . . . .
H6BA H 1.392710 0.212000 0.594928 0.043 Uiso 1 1 calc R U . . .
H6BB H 1.164940 0.167215 0.593707 0.043 Uiso 1 1 calc R U . . .
C7B C 1.2210(13) 0.2421(4) 0.4459(4) 0.0333(15) Uani 1 1 d . . . . .
H7BA H 1.189237 0.195814 0.430278 0.040 Uiso 1 1 calc R U . . .
H7BB H 1.389260 0.247301 0.451388 0.040 Uiso 1 1 calc R U . . .
C8B C 1.1290(12) 0.2879(4) 0.3791(4) 0.0298(14) Uani 1 1 d . . . . .
C9B C 0.9267(16) 0.2724(6) 0.3366(5) 0.048(2) Uani 1 1 d . . . . .
H9B H 0.843807 0.234049 0.349948 0.058 Uiso 1 1 calc R U . . .
C10B C 0.8423(17) 0.3133(6) 0.2734(6) 0.056(3) Uani 1 1 d . . . . .
H10B H 0.704520 0.302365 0.244743 0.068 Uiso 1 1 calc R U . . .
C11B C 0.9662(18) 0.3697(5) 0.2544(5) 0.048(2) Uani 1 1 d . . . . .
C12B C 1.167(2) 0.3872(5) 0.2964(6) 0.052(2) Uani 1 1 d . . . . .
H12B H 1.247144 0.426125 0.283614 0.062 Uiso 1 1 calc R U . . .
C13B C 1.2501(16) 0.3455(4) 0.3593(5) 0.0420(18) Uani 1 1 d . . . . .
H13B H 1.387689 0.356633 0.387964 0.050 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
I1 C11 2.101(8) . ?
O1 C2 1.519(8) . ?
O1 C3 1.370(9) . ?
O2 C3 1.195(9) . ?
C1 H1 0.9800 . ?
C1 C2 1.532(10) . ?
C1 C3 1.500(9) . ?
C1 C4 1.539(11) . ?
C2 C6 1.514(11) . ?
C2 C7 1.503(11) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.528(13) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.539(15) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.513(10) . ?
C8 C9 1.398(9) . ?
C8 C13 1.397(10) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(11) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(11) . ?
C11 C12 1.390(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.370(11) . ?
C13 H13 0.9300 . ?
I1A C11A 2.098(7) . ?
O1A C2A 1.509(7) . ?
O1A C3A 1.358(9) . ?
O2A C3A 1.199(10) . ?
C1A H1A 0.9800 . ?
C1A C2A 1.551(8) . ?
C1A C3A 1.506(9) . ?
C1A C4A 1.528(10) . ?
C2A C6A 1.520(10) . ?
C2A C7A 1.505(9) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A C5A 1.536(11) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A C6A 1.537(9) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C7A C8A 1.512(9) . ?
C8A C9A 1.386(9) . ?
C8A C13A 1.388(10) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.379(10) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.394(10) . ?
C11A C12A 1.383(10) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.392(11) . ?
C13A H13A 0.9300 . ?
I1B C11B 2.108(8) . ?
O1B C2B 1.523(8) . ?
O1B C3B 1.354(10) . ?
O2B C3B 1.197(10) . ?
C1B H1B 0.9800 . ?
C1B C2B 1.539(11) . ?
C1B C3B 1.501(9) . ?
C1B C4B 1.529(11) . ?
C2B C3B 2.037(10) . ?
C2B C6B 1.518(10) . ?
C2B C7B 1.503(10) . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?
C4B C5B 1.535(14) . ?
C5B H5BA 0.9700 . ?
C5B H5BB 0.9700 . ?
C5B C6B 1.533(12) . ?
C6B H6BA 0.9700 . ?
C6B H6BB 0.9700 . ?
C7B H7BA 0.9700 . ?
C7B H7BB 0.9700 . ?
C7B C8B 1.516(10) . ?
C8B C9B 1.366(11) . ?
C8B C13B 1.385(11) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.401(14) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.372(16) . ?
C11B C12B 1.364(15) . ?
C12B H12B 0.9300 . ?
C12B C13B 1.403(13) . ?
C13B H13B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 90.3(5) . . ?
C2 C1 H1 115.9 . . ?
C2 C1 C4 106.5(6) . . ?
C3 C1 H1 115.9 . . ?
C3 C1 C2 85.1(5) . . ?
C3 C1 C4 113.5(6) . . ?
C4 C1 H1 115.9 . . ?
O1 C2 C1 88.6(5) . . ?
C6 C2 O1 109.3(6) . . ?
C6 C2 C1 106.7(6) . . ?
C7 C2 O1 110.0(6) . . ?
C7 C2 C1 122.5(6) . . ?
C7 C2 C6 116.1(6) . . ?
O1 C3 C1 95.8(5) . . ?
O2 C3 O1 125.3(7) . . ?
O2 C3 C1 138.8(7) . . ?
C1 C4 H4A 110.9 . . ?
C1 C4 H4B 110.9 . . ?
H4A C4 H4B 109.0 . . ?
C5 C4 C1 104.1(7) . . ?
C5 C4 H4A 110.9 . . ?
C5 C4 H4B 110.9 . . ?
C4 C5 H5A 111.1 . . ?
C4 C5 H5B 111.1 . . ?
C4 C5 C6 103.2(7) . . ?
H5A C5 H5B 109.1 . . ?
C6 C5 H5A 111.1 . . ?
C6 C5 H5B 111.1 . . ?
C2 C6 C5 104.8(7) . . ?
C2 C6 H6A 110.8 . . ?
C2 C6 H6B 110.8 . . ?
C5 C6 H6A 110.8 . . ?
C5 C6 H6B 110.8 . . ?
H6A C6 H6B 108.9 . . ?
C2 C7 H7A 108.3 . . ?
C2 C7 H7B 108.3 . . ?
C2 C7 C8 116.0(6) . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
C9 C8 C7 121.2(6) . . ?
C13 C8 C7 120.9(6) . . ?
C13 C8 C9 117.8(7) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(7) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.8(6) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 I1 119.4(5) . . ?
C10 C11 C12 120.3(7) . . ?
C12 C11 I1 120.3(6) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.4(7) . . ?
C13 C12 H12 120.3 . . ?
C8 C13 H13 119.0 . . ?
C12 C13 C8 121.9(6) . . ?
C12 C13 H13 119.0 . . ?
C3A O1A C2A 91.1(5) . . ?
C2A C1A H1A 116.1 . . ?
C3A C1A H1A 116.1 . . ?
C3A C1A C2A 84.2(5) . . ?
C3A C1A C4A 113.5(6) . . ?
C4A C1A H1A 116.1 . . ?
C4A C1A C2A 106.3(5) . . ?
O1A C2A C1A 88.3(4) . . ?
O1A C2A C6A 109.4(5) . . ?
C6A C2A C1A 106.3(5) . . ?
C7A C2A O1A 110.0(5) . . ?
C7A C2A C1A 119.6(5) . . ?
C7A C2A C6A 118.9(6) . . ?
O1A C3A C1A 96.1(5) . . ?
O2A C3A O1A 126.0(7) . . ?
O2A C3A C1A 137.9(7) . . ?
C1A C4A H4AA 110.8 . . ?
C1A C4A H4AB 110.8 . . ?
C1A C4A C5A 104.6(6) . . ?
H4AA C4A H4AB 108.9 . . ?
C5A C4A H4AA 110.8 . . ?
C5A C4A H4AB 110.8 . . ?
C4A C5A H5AA 111.1 . . ?
C4A C5A H5AB 111.1 . . ?
C4A C5A C6A 103.1(6) . . ?
H5AA C5A H5AB 109.1 . . ?
C6A C5A H5AA 111.1 . . ?
C6A C5A H5AB 111.1 . . ?
C2A C6A C5A 104.6(6) . . ?
C2A C6A H6AA 110.8 . . ?
C2A C6A H6AB 110.8 . . ?
C5A C6A H6AA 110.8 . . ?
C5A C6A H6AB 110.8 . . ?
H6AA C6A H6AB 108.9 . . ?
C2A C7A H7AA 108.8 . . ?
C2A C7A H7AB 108.8 . . ?
C2A C7A C8A 113.9(5) . . ?
H7AA C7A H7AB 107.7 . . ?
C8A C7A H7AA 108.8 . . ?
C8A C7A H7AB 108.8 . . ?
C9A C8A C7A 121.2(6) . . ?
C9A C8A C13A 118.3(6) . . ?
C13A C8A C7A 120.5(6) . . ?
C8A C9A H9A 119.2 . . ?
C10A C9A C8A 121.6(6) . . ?
C10A C9A H9A 119.2 . . ?
C9A C10A H10A 120.4 . . ?
C9A C10A C11A 119.2(6) . . ?
C11A C10A H10A 120.4 . . ?
C10A C11A I1A 120.2(5) . . ?
C12A C11A I1A 119.3(5) . . ?
C12A C11A C10A 120.5(6) . . ?
C11A C12A H12A 120.5 . . ?
C11A C12A C13A 119.1(7) . . ?
C13A C12A H12A 120.5 . . ?
C8A C13A C12A 121.3(6) . . ?
C8A C13A H13A 119.3 . . ?
C12A C13A H13A 119.3 . . ?
C3B O1B C2B 90.0(5) . . ?
C2B C1B H1B 116.3 . . ?
C3B C1B H1B 116.3 . . ?
C3B C1B C2B 84.2(5) . . ?
C3B C1B C4B 112.7(6) . . ?
C4B C1B H1B 116.3 . . ?
C4B C1B C2B 106.5(6) . . ?
O1B C2B C1B 88.7(5) . . ?
O1B C2B C3B 41.6(3) . . ?
C1B C2B C3B 47.1(4) . . ?
C6B C2B O1B 109.8(6) . . ?
C6B C2B C1B 106.9(6) . . ?
C6B C2B C3B 118.2(5) . . ?
C7B C2B O1B 109.4(5) . . ?
C7B C2B C1B 122.2(6) . . ?
C7B C2B C3B 124.7(5) . . ?
C7B C2B C6B 116.2(6) . . ?
O1B C3B C1B 97.0(6) . . ?
O1B C3B C2B 48.4(4) . . ?
O2B C3B O1B 125.8(7) . . ?
O2B C3B C1B 137.2(8) . . ?
O2B C3B C2B 173.7(7) . . ?
C1B C3B C2B 48.7(4) . . ?
C1B C4B H4BA 110.9 . . ?
C1B C4B H4BB 110.9 . . ?
C1B C4B C5B 104.2(7) . . ?
H4BA C4B H4BB 108.9 . . ?
C5B C4B H4BA 110.9 . . ?
C5B C4B H4BB 110.9 . . ?
C4B C5B H5BA 111.0 . . ?
C4B C5B H5BB 111.0 . . ?
H5BA C5B H5BB 109.0 . . ?
C6B C5B C4B 103.7(7) . . ?
C6B C5B H5BA 111.0 . . ?
C6B C5B H5BB 111.0 . . ?
C2B C6B C5B 104.2(6) . . ?
C2B C6B H6BA 110.9 . . ?
C2B C6B H6BB 110.9 . . ?
C5B C6B H6BA 110.9 . . ?
C5B C6B H6BB 110.9 . . ?
H6BA C6B H6BB 108.9 . . ?
C2B C7B H7BA 108.5 . . ?
C2B C7B H7BB 108.5 . . ?
C2B C7B C8B 115.1(6) . . ?
H7BA C7B H7BB 107.5 . . ?
C8B C7B H7BA 108.5 . . ?
C8B C7B H7BB 108.5 . . ?
C9B C8B C7B 120.3(7) . . ?
C9B C8B C13B 119.1(8) . . ?
C13B C8B C7B 120.6(7) . . ?
C8B C9B H9B 119.5 . . ?
C8B C9B C10B 121.1(9) . . ?
C10B C9B H9B 119.5 . . ?
C9B C10B H10B 120.6 . . ?
C11B C10B C9B 118.9(9) . . ?
C11B C10B H10B 120.6 . . ?
C10B C11B I1B 118.2(7) . . ?
C12B C11B I1B 120.2(8) . . ?
C12B C11B C10B 121.5(8) . . ?
C11B C12B H12B 120.5 . . ?
C11B C12B C13B 119.0(9) . . ?
C13B C12B H12B 120.5 . . ?
C8B C13B C12B 120.5(8) . . ?
C8B C13B H13B 119.8 . . ?
C12B C13B H13B 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C11 C12 C13 -178.8(5) . . . . ?
O1 C2 C6 C5 -72.2(7) . . . . ?
O1 C2 C7 C8 59.7(7) . . . . ?
C1 C2 C6 C5 22.3(8) . . . . ?
C1 C2 C7 C8 -41.9(9) . . . . ?
C1 C4 C5 C6 37.0(8) . . . . ?
C2 O1 C3 O2 -179.8(9) . . . . ?
C2 O1 C3 C1 -2.8(6) . . . . ?
C2 C1 C3 O1 2.8(6) . . . . ?
C2 C1 C3 O2 179.1(11) . . . . ?
C2 C1 C4 C5 -23.6(8) . . . . ?
C2 C7 C8 C9 -77.1(8) . . . . ?
C2 C7 C8 C13 105.4(7) . . . . ?
C3 O1 C2 C1 2.8(6) . . . . ?
C3 O1 C2 C6 110.0(7) . . . . ?
C3 O1 C2 C7 -121.5(6) . . . . ?
C3 C1 C2 O1 -2.5(5) . . . . ?
C3 C1 C2 C6 -112.3(6) . . . . ?
C3 C1 C2 C7 110.4(7) . . . . ?
C3 C1 C4 C5 68.3(8) . . . . ?
C4 C1 C2 O1 110.5(6) . . . . ?
C4 C1 C2 C6 0.7(8) . . . . ?
C4 C1 C2 C7 -136.6(7) . . . . ?
C4 C1 C3 O1 -103.0(7) . . . . ?
C4 C1 C3 O2 73.2(13) . . . . ?
C4 C5 C6 C2 -36.9(8) . . . . ?
C6 C2 C7 C8 -175.7(6) . . . . ?
C7 C2 C6 C5 162.7(7) . . . . ?
C7 C8 C9 C10 -176.6(6) . . . . ?
C7 C8 C13 C12 177.2(6) . . . . ?
C8 C9 C10 C11 -0.5(10) . . . . ?
C9 C8 C13 C12 -0.3(10) . . . . ?
C9 C10 C11 I1 179.4(5) . . . . ?
C9 C10 C11 C12 -0.5(10) . . . . ?
C10 C11 C12 C13 1.1(10) . . . . ?
C11 C12 C13 C8 -0.7(11) . . . . ?
C13 C8 C9 C10 0.9(10) . . . . ?
I1A C11A C12A C13A -179.8(6) . . . . ?
O1A C2A C6A C5A -70.0(7) . . . . ?
O1A C2A C7A C8A -64.5(7) . . . . ?
C1A C2A C6A C5A 24.0(7) . . . . ?
C1A C2A C7A C8A -164.3(5) . . . . ?
C1A C4A C5A C6A 37.0(8) . . . . ?
C2A O1A C3A O2A 177.3(9) . . . . ?
C2A O1A C3A C1A -4.7(6) . . . . ?
C2A C1A C3A O1A 4.6(6) . . . . ?
C2A C1A C3A O2A -177.8(12) . . . . ?
C2A C1A C4A C5A -22.3(7) . . . . ?
C2A C7A C8A C9A 85.5(8) . . . . ?
C2A C7A C8A C13A -93.3(7) . . . . ?
C3A O1A C2A C1A 4.5(6) . . . . ?
C3A O1A C2A C6A 111.2(6) . . . . ?
C3A O1A C2A C7A -116.4(6) . . . . ?
C3A C1A C2A O1A -4.1(5) . . . . ?
C3A C1A C2A C6A -113.9(6) . . . . ?
C3A C1A C2A C7A 108.0(6) . . . . ?
C3A C1A C4A C5A 68.4(7) . . . . ?
C4A C1A C2A O1A 108.7(5) . . . . ?
C4A C1A C2A C6A -1.1(7) . . . . ?
C4A C1A C2A C7A -139.2(6) . . . . ?
C4A C1A C3A O1A -100.7(6) . . . . ?
C4A C1A C3A O2A 76.9(13) . . . . ?
C4A C5A C6A C2A -37.8(7) . . . . ?
C6A C2A C7A C8A 62.7(7) . . . . ?
C7A C2A C6A C5A 162.5(6) . . . . ?
C7A C8A C9A C10A -178.9(6) . . . . ?
C7A C8A C13A C12A 179.0(7) . . . . ?
C8A C9A C10A C11A 0.3(11) . . . . ?
C9A C8A C13A C12A 0.1(11) . . . . ?
C9A C10A C11A I1A 180.0(6) . . . . ?
C9A C10A C11A C12A -0.7(11) . . . . ?
C10A C11A C12A C13A 0.9(12) . . . . ?
C11A C12A C13A C8A -0.6(12) . . . . ?
C13A C8A C9A C10A 0.0(11) . . . . ?
I1B C11B C12B C13B -175.4(7) . . . . ?
O1B C2B C6B C5B -71.2(8) . . . . ?
O1B C2B C7B C8B 59.8(8) . . . . ?
C1B C2B C6B C5B 23.6(8) . . . . ?
C1B C2B C7B C8B -41.3(9) . . . . ?
C1B C4B C5B C6B 36.4(8) . . . . ?
C2B O1B C3B O2B 177.0(9) . . . . ?
C2B O1B C3B C1B -3.2(6) . . . . ?
C2B C1B C3B O1B 3.1(6) . . . . ?
C2B C1B C3B O2B -177.1(11) . . . . ?
C2B C1B C4B C5B -21.8(7) . . . . ?
C2B C7B C8B C9B -85.2(9) . . . . ?
C2B C7B C8B C13B 95.8(9) . . . . ?
C3B O1B C2B C1B 3.1(5) . . . . ?
C3B O1B C2B C6B 110.5(7) . . . . ?
C3B O1B C2B C7B -120.8(7) . . . . ?
C3B C1B C2B O1B -2.8(5) . . . . ?
C3B C1B C2B C6B -113.1(6) . . . . ?
C3B C1B C2B C7B 109.4(7) . . . . ?
C3B C1B C4B C5B 68.7(8) . . . . ?
C3B C2B C6B C5B -26.3(8) . . . . ?
C3B C2B C7B C8B 15.9(9) . . . . ?
C4B C1B C2B O1B 109.2(6) . . . . ?
C4B C1B C2B C3B 112.0(7) . . . . ?
C4B C1B C2B C6B -1.1(7) . . . . ?
C4B C1B C2B C7B -138.6(7) . . . . ?
C4B C1B C3B O1B -102.3(7) . . . . ?
C4B C1B C3B O2B 77.5(13) . . . . ?
C4B C1B C3B C2B -105.4(7) . . . . ?
C4B C5B C6B C2B -37.1(8) . . . . ?
C6B C2B C7B C8B -175.1(6) . . . . ?
C7B C2B C6B C5B 164.0(7) . . . . ?
C7B C8B C9B C10B -178.4(9) . . . . ?
C7B C8B C13B C12B 178.8(8) . . . . ?
C8B C9B C10B C11B 0.0(16) . . . . ?
C9B C8B C13B C12B -0.2(13) . . . . ?
C9B C10B C11B I1B 175.9(8) . . . . ?
C9B C10B C11B C12B -1.0(15) . . . . ?
C10B C11B C12B C13B 1.4(15) . . . . ?
C11B C12B C13B C8B -0.8(14) . . . . ?
C13B C8B C9B C10B 0.6(14) . . . . ?

_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 2.071
_oxdiff_exptl_absorpt_empirical_full_min 0.561
####################################################################### 
# 
# 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_mx9365
_database_code_depnum_ccdc_archive 'CCDC 2211978'
loop_
_audit_author_name
_audit_author_address
'Song Ye'
;Institute of Chemistry, CAS
China
;
_audit_update_record             
;
2022-10-10 deposited with the CCDC.	2022-12-20 downloaded from the CCDC.
;
_audit_creation_date             2021-05-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 Br O2'
_chemical_formula_sum            'C12 H11 Br O2'
_chemical_formula_weight         267.12
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHOBr
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           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                   6.0227(3)
_cell_length_b                   6.9189(3)
_cell_length_c                   25.7398(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1072.59(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6556
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      27.8410
_cell_measurement_theta_min      1.5630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.808
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            19510
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.052
_diffrn_reflns_theta_min         1.582
_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 0.912
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  94.00   0.50   13.00    --    5.00  45.00  30.00  356
  2  ω     -6.00  21.00   0.50   13.00    --    5.00  45.00  30.00   54
  3  ω    -51.00  77.00   0.50   13.00    --  -11.40  45.00 167.54  256
  4  ω    -95.00  71.00   0.50   13.00    --  -11.40  45.00 120.00  332
  5  ω    -97.00 -70.00   0.50   13.00    --  -11.40  45.00 167.54   54
  6  ω    -77.00  34.00   0.50   13.00    --  -11.40  45.00  60.00  222
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0438320000
_diffrn_orient_matrix_UB_12      -0.0125263000
_diffrn_orient_matrix_UB_13      0.0253422000
_diffrn_orient_matrix_UB_21      -0.0895399000
_diffrn_orient_matrix_UB_22      -0.0543624000
_diffrn_orient_matrix_UB_23      -0.0103870000
_diffrn_orient_matrix_UB_31      0.0628303000
_diffrn_orient_matrix_UB_32      -0.0859782000
_diffrn_orient_matrix_UB_33      0.0029504000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.633
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.817
_reflns_number_gt                2414
_reflns_number_total             2996
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.918
_refine_diff_density_min         -0.702
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details 
;
 Flack x determined using 778 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2996
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0555
_refine_ls_restrained_S_all      1.053
_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)+(0.0597P)²+1.0113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1165
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Riding coordinates:
 C2(H2)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
2.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
2.d Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.84866(11) 0.59799(8) 0.15355(2) 0.03373(19) Uani 1 1 d . . . . .
O1 O 0.7636(8) 0.7410(7) 0.47814(16) 0.0392(11) Uani 1 1 d . . . . .
O2 O 0.7437(9) 0.5071(9) 0.53960(19) 0.0531(14) Uani 1 1 d . . . . .
C1 C 0.6372(11) 0.6890(9) 0.3881(2) 0.0288(12) Uani 1 1 d . . . . .
H1 H 0.558921 0.811526 0.393430 0.035 Uiso 1 1 calc R U . . .
C2 C 0.8315(11) 0.6764(9) 0.4251(2) 0.0317(13) Uani 1 1 d . . . . .
H2 H 0.968438 0.729757 0.412448 0.038 Uiso 1 1 d R U . . .
C3 C 0.8452(12) 0.4671(9) 0.4452(2) 0.0352(13) Uani 1 1 d . . . . .
H3 H 0.991059 0.404597 0.443720 0.042 Uiso 1 1 calc R U . . .
C4 C 0.7809(11) 0.5577(11) 0.4961(3) 0.0396(16) Uani 1 1 d . . . . .
C5 C 0.6529(13) 0.3603(9) 0.4193(3) 0.0391(14) Uani 1 1 d . . . . .
H5A H 0.702507 0.293643 0.388199 0.047 Uiso 1 1 calc R U . . .
H5B H 0.587266 0.267028 0.442825 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4877(10) 0.5195(10) 0.4058(2) 0.0356(15) Uani 1 1 d . . . . .
H6A H 0.399731 0.555326 0.435846 0.043 Uiso 1 1 calc R U . . .
H6B H 0.388930 0.479115 0.378051 0.043 Uiso 1 1 calc R U . . .
C7 C 0.7001(9) 0.6687(8) 0.3311(2) 0.0259(12) Uani 1 1 d . . . . .
C8 C 0.5461(11) 0.7206(9) 0.2934(2) 0.0287(12) Uani 1 1 d . . . . .
H8 H 0.409855 0.770368 0.303879 0.034 Uiso 1 1 calc R U . . .
C9 C 0.5879(9) 0.7008(9) 0.2410(2) 0.0274(13) Uani 1 1 d . . . . .
H9 H 0.481152 0.735237 0.216540 0.033 Uiso 1 1 calc R U . . .
C10 C 0.7917(9) 0.6288(7) 0.2254(2) 0.0234(12) Uani 1 1 d . . . . .
C11 C 0.9496(10) 0.5753(9) 0.2612(2) 0.0288(12) Uani 1 1 d . . . . .
H11 H 1.085904 0.526718 0.250329 0.035 Uiso 1 1 calc R U . . .
C12 C 0.9030(9) 0.5949(9) 0.3141(2) 0.0287(12) Uani 1 1 d . . . . .
H12 H 1.009150 0.558069 0.338380 0.034 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
Br1 C10 1.893(5) . ?
O1 C2 1.494(7) . ?
O1 C4 1.354(9) . ?
O2 C4 1.195(8) . ?
C1 H1 0.9800 . ?
C1 C2 1.510(9) . ?
C1 C6 1.547(9) . ?
C1 C7 1.522(8) . ?
C2 H2 0.9600 . ?
C2 C3 1.541(9) . ?
C2 C4 2.027(9) . ?
C3 H3 0.9800 . ?
C3 C4 1.502(9) . ?
C3 C5 1.527(10) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.525(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.389(8) . ?
C7 C12 1.395(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(8) . ?
C10 C11 1.375(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.396(8) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C2 90.6(5) . . ?
C2 C1 H1 109.5 . . ?
C2 C1 C6 102.9(5) . . ?
C2 C1 C7 114.2(5) . . ?
C6 C1 H1 109.5 . . ?
C7 C1 H1 109.5 . . ?
C7 C1 C6 111.0(5) . . ?
O1 C2 C1 110.3(5) . . ?
O1 C2 H2 115.4 . . ?
O1 C2 C3 89.3(4) . . ?
O1 C2 C4 41.9(3) . . ?
C1 C2 H2 115.5 . . ?
C1 C2 C3 107.9(5) . . ?
C1 C2 C4 118.3(5) . . ?
C3 C2 H2 115.4 . . ?
C3 C2 C4 47.4(3) . . ?
C4 C2 H2 126.1 . . ?
C2 C3 H3 116.7 . . ?
C4 C3 C2 83.5(5) . . ?
C4 C3 H3 116.7 . . ?
C4 C3 C5 112.8(6) . . ?
C5 C3 C2 105.5(5) . . ?
C5 C3 H3 116.7 . . ?
O1 C4 C2 47.5(3) . . ?
O1 C4 C3 96.5(5) . . ?
O2 C4 O1 125.4(7) . . ?
O2 C4 C2 172.9(7) . . ?
O2 C4 C3 138.0(7) . . ?
C3 C4 C2 49.1(4) . . ?
C3 C5 H5A 110.9 . . ?
C3 C5 H5B 110.9 . . ?
H5A C5 H5B 108.9 . . ?
C6 C5 C3 104.2(5) . . ?
C6 C5 H5A 110.9 . . ?
C6 C5 H5B 110.9 . . ?
C1 C6 H6A 111.0 . . ?
C1 C6 H6B 111.0 . . ?
C5 C6 C1 103.6(5) . . ?
C5 C6 H6A 111.0 . . ?
C5 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
C8 C7 C1 118.9(5) . . ?
C8 C7 C12 117.4(5) . . ?
C12 C7 C1 123.6(5) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 C7 122.4(6) . . ?
C9 C8 H8 118.8 . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.7(5) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 Br1 119.0(4) . . ?
C11 C10 Br1 119.9(4) . . ?
C11 C10 C9 121.1(5) . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.2(5) . . ?
C12 C11 H11 120.4 . . ?
C7 C12 C11 121.2(5) . . ?
C7 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?

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
Br1 C10 C11 C12 -178.6(5) . . . . ?
O1 C2 C3 C4 -1.3(5) . . . . ?
O1 C2 C3 C5 110.7(5) . . . . ?
C1 C2 C3 C4 -112.4(5) . . . . ?
C1 C2 C3 C5 -0.4(7) . . . . ?
C1 C7 C8 C9 -177.9(5) . . . . ?
C1 C7 C12 C11 178.4(6) . . . . ?
C2 O1 C4 O2 -179.3(7) . . . . ?
C2 O1 C4 C3 -1.4(5) . . . . ?
C2 C1 C6 C5 -38.4(6) . . . . ?
C2 C1 C7 C8 -165.7(6) . . . . ?
C2 C1 C7 C12 16.3(8) . . . . ?
C2 C3 C4 O1 1.4(5) . . . . ?
C2 C3 C4 O2 178.9(9) . . . . ?
C2 C3 C5 C6 -23.6(6) . . . . ?
C3 C5 C6 C1 38.6(6) . . . . ?
C4 O1 C2 C1 110.3(6) . . . . ?
C4 O1 C2 C3 1.4(5) . . . . ?
C4 C2 C3 C5 111.9(6) . . . . ?
C4 C3 C5 C6 65.8(6) . . . . ?
C5 C3 C4 O1 -102.7(6) . . . . ?
C5 C3 C4 O2 74.7(10) . . . . ?
C5 C3 C4 C2 -104.1(6) . . . . ?
C6 C1 C2 O1 -72.2(6) . . . . ?
C6 C1 C2 C3 23.8(7) . . . . ?
C6 C1 C2 C4 -26.9(7) . . . . ?
C6 C1 C7 C8 78.6(7) . . . . ?
C6 C1 C7 C12 -99.4(7) . . . . ?
C7 C1 C2 O1 167.4(5) . . . . ?
C7 C1 C2 C3 -96.6(6) . . . . ?
C7 C1 C2 C4 -147.2(5) . . . . ?
C7 C1 C6 C5 84.1(6) . . . . ?
C7 C8 C9 C10 -0.8(9) . . . . ?
C8 C7 C12 C11 0.4(9) . . . . ?
C8 C9 C10 Br1 179.1(4) . . . . ?
C8 C9 C10 C11 0.8(8) . . . . ?
C9 C10 C11 C12 -0.2(9) . . . . ?
C10 C11 C12 C7 -0.4(9) . . . . ?
C12 C7 C8 C9 0.2(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.644
_oxdiff_exptl_absorpt_empirical_full_min 0.539
