# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_p21n_sq
_database_code_depnum_ccdc_archive 'CCDC 1976911'
loop_
_audit_author_name
_audit_author_address
'Sota Sato'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2020-01-11 deposited with the CCDC.	2020-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C84 H48, C6 H3 Cl3'
_chemical_formula_sum            'C90 H51 Cl3'
_chemical_formula_weight         1238.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0038 0.0019 '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 0.1650 0.1824 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   7.6200(15)
_cell_length_b                   43.657(16)
_cell_length_c                   25.190(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.53(3)
_cell_angle_gamma                90
_cell_volume                     8380(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    56129
_cell_measurement_theta_min      1.320
_cell_measurement_theta_max      27.241

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.982
_exptl_crystal_F_000             2568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.174
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'XDS (Kabsch, 2010)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.76000
_diffrn_radiation_type           synchrotron
_diffrn_source                   'SPring-8 BL38B1 bending magnet beamline'
_diffrn_measurement_device_type  'PAD Pilatus3 6M (Dectris)'
_diffrn_measurement_method       'oscillation method, ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            191760
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.320
_diffrn_reflns_theta_max         27.241
_diffrn_reflns_theta_full        27.129
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             15163
_reflns_number_gt                13715
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;

_computing_data_collection       'SPring-8 BSS'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'Superflip (Palatinus, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0876P)²+7.7080P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         15163
_refine_ls_number_parameters     920
_refine_ls_number_restraints     282
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.1941
_refine_ls_wR_factor_gt          0.1904
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1A C 0.2079(3) 0.30764(5) 0.70691(9) 0.0334(5) Uani 1 1 d . . . . .
H1A H 0.154255 0.308460 0.672738 0.040 Uiso 1 1 calc R U . . .
C2A C 0.2402(3) 0.27946(5) 0.73004(9) 0.0323(5) Uani 1 1 d . . . . .
C3A C 0.3154(3) 0.27895(5) 0.78128(9) 0.0338(5) Uani 1 1 d . . . . .
H3A H 0.334114 0.259841 0.798480 0.041 Uiso 1 1 calc R U . . .
C4A C 0.3621(3) 0.30546(5) 0.80684(9) 0.0329(5) Uani 1 1 d . . . . .
H4A H 0.413917 0.304291 0.841225 0.040 Uiso 1 1 calc R U . . .
C5A C 0.3353(3) 0.33432(5) 0.78350(9) 0.0315(5) Uani 1 1 d . . . . .
C6A C 0.3925(3) 0.36305(5) 0.80716(9) 0.0334(5) Uani 1 1 d . . . . .
C7A C 0.4850(3) 0.36405(5) 0.85589(9) 0.0377(5) Uani 1 1 d . . . . .
H7A H 0.502298 0.345621 0.875320 0.045 Uiso 1 1 calc R U . . .
C8A C 0.5506(4) 0.39091(6) 0.87588(10) 0.0447(6) Uani 1 1 d . . . . .
H8A H 0.610564 0.391062 0.909107 0.054 Uiso 1 1 calc R U . . .
C9A C 0.5291(4) 0.41809(6) 0.84733(11) 0.0496(7) Uani 1 1 d . . . . .
H9A H 0.579115 0.436572 0.860402 0.060 Uiso 1 1 calc R U . . .
C10A C 0.4366(4) 0.41819(6) 0.80078(10) 0.0449(6) Uani 1 1 d . . . . .
H10A H 0.421550 0.436903 0.782049 0.054 Uiso 1 1 calc R U . . .
C11A C 0.3626(3) 0.39106(5) 0.77979(9) 0.0360(5) Uani 1 1 d . . . . .
C12A C 0.2638(3) 0.39101(5) 0.73034(9) 0.0351(5) Uani 1 1 d . . . . .
C13A C 0.2149(3) 0.36396(5) 0.70841(9) 0.0347(5) Uani 1 1 d . . . . .
H13A H 0.153140 0.364151 0.675477 0.042 Uiso 1 1 calc R U . . .
C14A C 0.2526(3) 0.33515(5) 0.73287(9) 0.0324(5) Uani 1 1 d . . . . .
C15A C 0.2690(3) 0.42220(5) 0.64935(9) 0.0358(5) Uani 1 1 d . . . . .
H15A H 0.332151 0.405774 0.633787 0.043 Uiso 1 1 calc R U . . .
C16A C 0.2218(3) 0.41989(5) 0.70093(9) 0.0356(5) Uani 1 1 d . . . . .
C17A C 0.1226(3) 0.44443(5) 0.72497(9) 0.0368(5) Uani 1 1 d . . . . .
C18A C 0.0505(4) 0.44154(6) 0.77623(10) 0.0446(6) Uani 1 1 d . . . . .
H18A H 0.066437 0.422999 0.795430 0.054 Uiso 1 1 calc R U . . .
C19A C -0.0417(4) 0.46499(6) 0.79857(10) 0.0480(6) Uani 1 1 d . . . . .
H19A H -0.089805 0.462547 0.832965 0.058 Uiso 1 1 calc R U . . .
C20A C -0.0658(4) 0.49245(6) 0.77132(10) 0.0456(6) Uani 1 1 d . . . . .
H20A H -0.126239 0.508912 0.787701 0.055 Uiso 1 1 calc R U . . .
C21A C -0.0021(3) 0.49577(5) 0.72074(10) 0.0395(5) Uani 1 1 d . . . . .
H21A H -0.020045 0.514509 0.702313 0.047 Uiso 1 1 calc R U . . .
C22A C 0.0896(3) 0.47174(5) 0.69583(9) 0.0343(5) Uani 1 1 d . . . . .
C23A C 0.1440(3) 0.47385(5) 0.64075(9) 0.0325(5) Uani 1 1 d . . . . .
C24A C 0.1128(3) 0.49943(5) 0.60799(9) 0.0352(5) Uani 1 1 d . . . . .
H24A H 0.060194 0.517141 0.622918 0.042 Uiso 1 1 calc R U . . .
C25A C 0.1555(3) 0.49966(5) 0.55562(9) 0.0371(5) Uani 1 1 d . . . . .
H25A H 0.134560 0.517582 0.535121 0.045 Uiso 1 1 calc R U . . .
C26A C 0.2307(3) 0.47365(5) 0.53125(9) 0.0343(5) Uani 1 1 d . . . . .
C27A C 0.2677(3) 0.44865(5) 0.56315(9) 0.0349(5) Uani 1 1 d . . . . .
H27A H 0.321714 0.431182 0.547858 0.042 Uiso 1 1 calc R U . . .
C28A C 0.2279(3) 0.44831(5) 0.61743(9) 0.0343(5) Uani 1 1 d . . . . .
C29A C 0.2268(3) 0.44757(5) 0.44353(9) 0.0352(5) Uani 1 1 d . . . . .
H29A H 0.172193 0.430500 0.459939 0.042 Uiso 1 1 calc R U . . .
C30A C 0.2682(3) 0.47300(5) 0.47399(9) 0.0352(5) Uani 1 1 d . . . . .
C31A C 0.3474(3) 0.49822(5) 0.44799(9) 0.0368(5) Uani 1 1 d . . . . .
H31A H 0.372516 0.516349 0.467498 0.044 Uiso 1 1 calc R U . . .
C32A C 0.3880(3) 0.49684(5) 0.39541(9) 0.0369(5) Uani 1 1 d . . . . .
H32A H 0.443883 0.513914 0.379418 0.044 Uiso 1 1 calc R U . . .
C33A C 0.3499(3) 0.47106(5) 0.36421(9) 0.0344(5) Uani 1 1 d . . . . .
C34A C 0.3966(3) 0.46800(5) 0.30867(9) 0.0348(5) Uani 1 1 d . . . . .
C35A C 0.4942(3) 0.49079(6) 0.28247(10) 0.0409(5) Uani 1 1 d . . . . .
H35A H 0.526178 0.508913 0.301048 0.049 Uiso 1 1 calc R U . . .
C36A C 0.5440(4) 0.48724(6) 0.23040(10) 0.0428(6) Uani 1 1 d . . . . .
H36A H 0.609323 0.502892 0.213400 0.051 Uiso 1 1 calc R U . . .
C37A C 0.4986(3) 0.46068(6) 0.20252(10) 0.0419(5) Uani 1 1 d . . . . .
H37A H 0.533507 0.458268 0.166649 0.050 Uiso 1 1 calc R U . . .
C38A C 0.4038(3) 0.43810(5) 0.22695(10) 0.0395(5) Uani 1 1 d . . . . .
H38A H 0.374728 0.420033 0.207779 0.047 Uiso 1 1 calc R U . . .
C39A C 0.3485(3) 0.44117(5) 0.27987(9) 0.0345(5) Uani 1 1 d . . . . .
C40A C 0.2491(3) 0.41730(5) 0.30631(9) 0.0350(5) Uani 1 1 d . . . . .
C41A C 0.2127(3) 0.42023(5) 0.35849(9) 0.0359(5) Uani 1 1 d . . . . .
H41A H 0.150650 0.404171 0.375502 0.043 Uiso 1 1 calc R U . . .
C42A C 0.2632(3) 0.44633(5) 0.38930(9) 0.0351(5) Uani 1 1 d . . . . .
C43A C 0.2454(3) 0.36137(5) 0.30059(9) 0.0357(5) Uani 1 1 d . . . . .
H43A H 0.317187 0.361645 0.331612 0.043 Uiso 1 1 calc R U . . .
C44A C 0.1950(3) 0.38837(5) 0.27879(9) 0.0349(5) Uani 1 1 d . . . . .
C45A C 0.0799(3) 0.38830(5) 0.23252(9) 0.0334(5) Uani 1 1 d . . . . .
C46A C 0.0030(3) 0.41554(5) 0.21291(10) 0.0387(5) Uani 1 1 d . . . . .
H46A H 0.028872 0.434455 0.229915 0.046 Uiso 1 1 calc R U . . .
C47A C -0.1076(3) 0.41522(6) 0.17008(10) 0.0416(5) Uani 1 1 d . . . . .
H47A H -0.159060 0.433766 0.157827 0.050 Uiso 1 1 calc R U . . .
C48A C -0.1454(3) 0.38766(6) 0.14414(10) 0.0414(5) Uani 1 1 d . . . . .
H48A H -0.220351 0.387561 0.113797 0.050 Uiso 1 1 calc R U . . .
C49A C -0.0746(3) 0.36088(5) 0.16242(9) 0.0371(5) Uani 1 1 d . . . . .
H49A H -0.100041 0.342336 0.144190 0.045 Uiso 1 1 calc R U . . .
C50A C 0.0356(3) 0.36014(5) 0.20784(9) 0.0337(5) Uani 1 1 d . . . . .
C51A C 0.0975(3) 0.33142(5) 0.23075(9) 0.0322(5) Uani 1 1 d . . . . .
C52A C 0.0612(3) 0.30256(5) 0.20847(9) 0.0347(5) Uani 1 1 d . . . . .
H52A H 0.000604 0.301386 0.175414 0.042 Uiso 1 1 calc R U . . .
C53A C 0.1117(3) 0.27606(5) 0.23352(9) 0.0345(5) Uani 1 1 d . . . . .
H53A H 0.087685 0.256903 0.217119 0.041 Uiso 1 1 calc R U . . .
C54A C 0.1986(3) 0.27671(5) 0.28315(9) 0.0328(5) Uani 1 1 d . . . . .
C55A C 0.2410(3) 0.30494(5) 0.30437(9) 0.0343(5) Uani 1 1 d . . . . .
H55A H 0.303196 0.305855 0.337197 0.041 Uiso 1 1 calc R U . . .
C56A C 0.1944(3) 0.33241(5) 0.27858(9) 0.0329(5) Uani 1 1 d . . . . .
C57A C 0.2039(3) 0.24553(5) 0.36551(9) 0.0341(5) Uani 1 1 d . . . . .
H57A H 0.149099 0.262132 0.383219 0.041 Uiso 1 1 calc R U . . .
C58A C 0.2409(3) 0.24819(5) 0.31218(9) 0.0331(5) Uani 1 1 d . . . . .
C59A C 0.3182(3) 0.22298(5) 0.28691(9) 0.0359(5) Uani 1 1 d . . . . .
H59A H 0.339262 0.223895 0.249838 0.043 Uiso 1 1 calc R U . . .
C60A C 0.3639(3) 0.19704(5) 0.31452(9) 0.0344(5) Uani 1 1 d . . . . .
H60A H 0.419002 0.180636 0.296332 0.041 Uiso 1 1 calc R U . . .
C61A C 0.3312(3) 0.19421(5) 0.36908(9) 0.0321(5) Uani 1 1 d . . . . .
C62A C 0.3816(3) 0.16788(5) 0.40126(9) 0.0337(5) Uani 1 1 d . . . . .
C63A C 0.4800(3) 0.14348(5) 0.37957(10) 0.0385(5) Uani 1 1 d . . . . .
H63A H 0.510252 0.143987 0.343081 0.046 Uiso 1 1 calc R U . . .
C64A C 0.5323(4) 0.11913(6) 0.41016(10) 0.0439(6) Uani 1 1 d . . . . .
H64A H 0.597954 0.102954 0.394765 0.053 Uiso 1 1 calc R U . . .
C65A C 0.4892(4) 0.11802(6) 0.46432(10) 0.0427(6) Uani 1 1 d . . . . .
H65A H 0.524756 0.101080 0.485500 0.051 Uiso 1 1 calc R U . . .
C66A C 0.3953(3) 0.14161(5) 0.48640(9) 0.0375(5) Uani 1 1 d . . . . .
H66A H 0.368764 0.140967 0.523158 0.045 Uiso 1 1 calc R U . . .
C67A C 0.3375(3) 0.16668(5) 0.45584(9) 0.0337(5) Uani 1 1 d . . . . .
C68A C 0.2394(3) 0.19177(5) 0.47913(9) 0.0341(5) Uani 1 1 d . . . . .
C69A C 0.1995(3) 0.21650(5) 0.44886(9) 0.0345(5) Uani 1 1 d . . . . .
H69A H 0.138035 0.233010 0.464762 0.041 Uiso 1 1 calc R U . . .
C70A C 0.2453(3) 0.21891(5) 0.39423(9) 0.0330(5) Uani 1 1 d . . . . .
C71A C 0.2390(3) 0.21691(5) 0.56579(9) 0.0342(5) Uani 1 1 d . . . . .
H71A H 0.309138 0.232268 0.549729 0.041 Uiso 1 1 calc R U . . .
C72A C 0.1887(3) 0.19234(5) 0.53617(9) 0.0334(5) Uani 1 1 d . . . . .
C73A C 0.0749(3) 0.16945(5) 0.55963(9) 0.0335(5) Uani 1 1 d . . . . .
C74A C -0.0021(3) 0.14609(5) 0.52857(9) 0.0380(5) Uani 1 1 d . . . . .
H74A H 0.022006 0.145117 0.491674 0.046 Uiso 1 1 calc R U . . .
C75A C -0.1116(3) 0.12468(6) 0.55082(10) 0.0407(5) Uani 1 1 d . . . . .
H75A H -0.163607 0.109266 0.529213 0.049 Uiso 1 1 calc R U . . .
C76A C -0.1462(3) 0.12557(5) 0.60490(10) 0.0408(5) Uani 1 1 d . . . . .
H76A H -0.218842 0.110368 0.620354 0.049 Uiso 1 1 calc R U . . .
C77A C -0.0756(3) 0.14837(5) 0.63606(9) 0.0370(5) Uani 1 1 d . . . . .
H77A H -0.100777 0.148795 0.672915 0.044 Uiso 1 1 calc R U . . .
C78A C 0.0341(3) 0.17123(5) 0.61425(9) 0.0321(5) Uani 1 1 d . . . . .
C79A C 0.0959(3) 0.19700(5) 0.64566(9) 0.0315(5) Uani 1 1 d . . . . .
C80A C 0.0611(3) 0.20055(5) 0.70016(9) 0.0336(5) Uani 1 1 d . . . . .
H80A H 0.001610 0.184705 0.718550 0.040 Uiso 1 1 calc R U . . .
C81A C 0.1114(3) 0.22648(5) 0.72726(9) 0.0340(5) Uani 1 1 d . . . . .
H81A H 0.088246 0.228023 0.764155 0.041 Uiso 1 1 calc R U . . .
C82A C 0.1969(3) 0.25087(5) 0.70125(9) 0.0327(5) Uani 1 1 d . . . . .
C83A C 0.2367(3) 0.24733(5) 0.64844(9) 0.0334(5) Uani 1 1 d . . . . .
H83A H 0.296800 0.263299 0.630558 0.040 Uiso 1 1 calc R U . . .
C84A C 0.1906(3) 0.22057(5) 0.62019(9) 0.0318(5) Uani 1 1 d . . . . .
Cl1Y Cl 0.3647(11) -0.05046(19) 0.41182(16) 0.0486(11) Uani 0.347(2) 1 d D U P
A 2
Cl2Y Cl 0.2544(4) -0.05173(5) 0.55699(9) 0.0744(9) Uani 0.347(2) 1 d D U P A 2
Cl4Y Cl 0.1238(7) 0.05610(9) 0.55484(15) 0.0328(6) Uani 0.347(2) 1 d D U P A 2
C1Y C 0.306(5) -0.0243(4) 0.4614(7) 0.047(5) Uani 0.347(2) 1 d D U P A 2
C2Y C 0.256(2) -0.0196(3) 0.5159(6) 0.043(4) Uani 0.347(2) 1 d D U P A 2
C3Y C 0.203(2) 0.0067(5) 0.5422(8) 0.049(4) Uani 0.347(2) 1 d D U P A 2
H3Y H 0.180116 0.008158 0.579154 0.059 Uiso 0.347(2) 1 calc R U P A 2
C4Y C 0.190(4) 0.0297(4) 0.5073(6) 0.039(4) Uani 0.347(2) 1 d D U P A 2
C5Y C 0.2529(18) 0.0331(4) 0.4573(6) 0.055(4) Uani 0.347(2) 1 d D U P A 2
H5Y H 0.262559 0.052035 0.439072 0.066 Uiso 0.347(2) 1 calc R U P A 2
C6Y C 0.301(2) 0.0049(4) 0.4369(7) 0.050(4) Uani 0.347(2) 1 d D U P A 2
H6Y H 0.335534 0.005218 0.400772 0.060 Uiso 0.347(2) 1 calc R U P A 2
Cl1Z Cl 0.1284(5) 0.06379(7) 0.54610(14) 0.0849(10) Uani 0.653(2) 1 d D U P A 1
Cl2Z Cl 0.26122(17) -0.00417(2) 0.60812(4) 0.0546(4) Uani 0.653(2) 1 d D U P A
1
Cl4Z Cl 0.3722(6) -0.05348(10) 0.42860(12) 0.0659(8) Uani 0.653(2) 1 d D U P A
1
C1Z C 0.198(2) 0.0283(2) 0.5192(4) 0.043(2) Uani 0.653(2) 1 d D U P A 1
C2Z C 0.2537(11) 0.0001(2) 0.5392(3) 0.0394(17) Uani 0.653(2) 1 d D U P A 1
C3Z C 0.3057(12) -0.0248(2) 0.5099(4) 0.044(2) Uani 0.653(2) 1 d D U P A 1
H3Z H 0.344457 -0.043466 0.525292 0.053 Uiso 0.653(2) 1 calc R U P A 1
C4Z C 0.296(3) -0.0200(2) 0.4561(4) 0.040(3) Uani 0.653(2) 1 d D U P A 1
C5Z C 0.2355(9) 0.0053(2) 0.4302(4) 0.0462(17) Uani 0.653(2) 1 d D U P A 1
H5Z H 0.228078 0.006398 0.392554 0.055 Uiso 0.653(2) 1 calc R U P A 1
C6Z C 0.1852(9) 0.02920(17) 0.4628(3) 0.0435(15) Uani 0.653(2) 1 d D U P A 1
H6Z H 0.139359 0.047206 0.446684 0.052 Uiso 0.653(2) 1 calc R U P A 1


_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
C1A C2A 1.382(3) . ?
C1A C14A 1.408(3) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.408(3) . ?
C2A C82A 1.479(3) . ?
C3A C4A 1.370(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.405(3) . ?
C4A H4A 0.9500 . ?
C5A C14A 1.418(3) . ?
C5A C6A 1.454(3) . ?
C6A C7A 1.411(3) . ?
C6A C11A 1.421(3) . ?
C7A C8A 1.369(3) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.396(4) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.362(4) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.412(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.449(3) . ?
C12A C13A 1.355(3) . ?
C12A C16A 1.495(3) . ?
C13A C14A 1.428(3) . ?
C13A H13A 0.9500 . ?
C15A C16A 1.355(3) . ?
C15A C28A 1.428(3) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.447(3) . ?
C17A C18A 1.413(3) . ?
C17A C22A 1.421(3) . ?
C18A C19A 1.366(4) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.393(4) . ?
C19A H19A 0.9500 . ?
C20A C21A 1.375(4) . ?
C20A H20A 0.9500 . ?
C21A C22A 1.411(3) . ?
C21A H21A 0.9500 . ?
C22A C23A 1.455(3) . ?
C23A C24A 1.407(3) . ?
C23A C28A 1.416(3) . ?
C24A C25A 1.362(3) . ?
C24A H24A 0.9500 . ?
C25A C26A 1.414(3) . ?
C25A H25A 0.9500 . ?
C26A C27A 1.383(3) . ?
C26A C30A 1.473(3) . ?
C27A C28A 1.403(3) . ?
C27A H27A 0.9500 . ?
C29A C30A 1.384(3) . ?
C29A C42A 1.398(3) . ?
C29A H29A 0.9500 . ?
C30A C31A 1.419(3) . ?
C31A C32A 1.364(3) . ?
C31A H31A 0.9500 . ?
C32A C33A 1.401(3) . ?
C32A H32A 0.9500 . ?
C33A C42A 1.418(3) . ?
C33A C34A 1.453(3) . ?
C34A C35A 1.410(3) . ?
C34A C39A 1.424(3) . ?
C35A C36A 1.377(4) . ?
C35A H35A 0.9500 . ?
C36A C37A 1.397(3) . ?
C36A H36A 0.9500 . ?
C37A C38A 1.372(4) . ?
C37A H37A 0.9500 . ?
C38A C39A 1.408(3) . ?
C38A H38A 0.9500 . ?
C39A C40A 1.454(3) . ?
C40A C41A 1.352(3) . ?
C40A C44A 1.497(3) . ?
C41A C42A 1.429(3) . ?
C41A H41A 0.9500 . ?
C43A C44A 1.354(3) . ?
C43A C56A 1.433(3) . ?
C43A H43A 0.9500 . ?
C44A C45A 1.452(3) . ?
C45A C46A 1.413(3) . ?
C45A C50A 1.417(3) . ?
C46A C47A 1.363(4) . ?
C46A H46A 0.9500 . ?
C47A C48A 1.398(3) . ?
C47A H47A 0.9500 . ?
C48A C49A 1.366(3) . ?
C48A H48A 0.9500 . ?
C49A C50A 1.413(3) . ?
C49A H49A 0.9500 . ?
C50A C51A 1.457(3) . ?
C51A C52A 1.406(3) . ?
C51A C56A 1.408(3) . ?
C52A C53A 1.371(3) . ?
C52A H52A 0.9500 . ?
C53A C54A 1.409(3) . ?
C53A H53A 0.9500 . ?
C54A C55A 1.381(3) . ?
C54A C58A 1.478(3) . ?
C55A C56A 1.408(3) . ?
C55A H55A 0.9500 . ?
C57A C58A 1.380(3) . ?
C57A C70A 1.403(3) . ?
C57A H57A 0.9500 . ?
C58A C59A 1.404(3) . ?
C59A C60A 1.372(3) . ?
C59A H59A 0.9500 . ?
C60A C61A 1.404(3) . ?
C60A H60A 0.9500 . ?
C61A C70A 1.414(3) . ?
C61A C62A 1.456(3) . ?
C62A C63A 1.415(3) . ?
C62A C67A 1.419(3) . ?
C63A C64A 1.370(3) . ?
C63A H63A 0.9500 . ?
C64A C65A 1.407(4) . ?
C64A H64A 0.9500 . ?
C65A C66A 1.374(3) . ?
C65A H65A 0.9500 . ?
C66A C67A 1.406(3) . ?
C66A H66A 0.9500 . ?
C67A C68A 1.453(3) . ?
C68A C69A 1.355(3) . ?
C68A C72A 1.492(3) . ?
C69A C70A 1.427(3) . ?
C69A H69A 0.9500 . ?
C71A C72A 1.360(3) . ?
C71A C84A 1.431(3) . ?
C71A H71A 0.9500 . ?
C72A C73A 1.452(3) . ?
C73A C74A 1.410(3) . ?
C73A C78A 1.416(3) . ?
C74A C75A 1.376(3) . ?
C74A H74A 0.9500 . ?
C75A C76A 1.390(4) . ?
C75A H75A 0.9500 . ?
C76A C77A 1.374(3) . ?
C76A H76A 0.9500 . ?
C77A C78A 1.416(3) . ?
C77A H77A 0.9500 . ?
C78A C79A 1.452(3) . ?
C79A C80A 1.409(3) . ?
C79A C84A 1.414(3) . ?
C80A C81A 1.374(3) . ?
C80A H80A 0.9500 . ?
C81A C82A 1.413(3) . ?
C81A H81A 0.9500 . ?
C82A C83A 1.376(3) . ?
C83A C84A 1.410(3) . ?
C83A H83A 0.9500 . ?
Cl1Y C1Y 1.753(10) . ?
Cl2Y C2Y 1.744(9) . ?
Cl4Y C4Y 1.739(9) . ?
C1Y C6Y 1.419(17) . ?
C1Y C2Y 1.443(16) . ?
C2Y C3Y 1.387(15) . ?
C3Y C4Y 1.339(17) . ?
C3Y H3Y 0.9500 . ?
C4Y C5Y 1.358(16) . ?
C5Y C6Y 1.383(16) . ?
C5Y H5Y 0.9500 . ?
C6Y H6Y 0.9500 . ?
Cl1Z C1Z 1.776(8) . ?
Cl2Z C2Z 1.746(9) . ?
Cl4Z C4Z 1.722(7) . ?
C1Z C2Z 1.393(11) . ?
C1Z C6Z 1.422(10) . ?
C2Z C3Z 1.375(10) . ?
C3Z C4Z 1.370(11) . ?
C3Z H3Z 0.9500 . ?
C4Z C5Z 1.360(11) . ?
C5Z C6Z 1.386(9) . ?
C5Z H5Z 0.9500 . ?
C6Z H6Z 0.9500 . ?

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
C2A C1A C14A 121.5(2) . . ?
C2A C1A H1A 119.3 . . ?
C14A C1A H1A 119.3 . . ?
C1A C2A C3A 118.0(2) . . ?
C1A C2A C82A 120.4(2) . . ?
C3A C2A C82A 121.56(19) . . ?
C4A C3A C2A 121.3(2) . . ?
C4A C3A H3A 119.4 . . ?
C2A C3A H3A 119.4 . . ?
C3A C4A C5A 121.7(2) . . ?
C3A C4A H4A 119.2 . . ?
C5A C4A H4A 119.2 . . ?
C4A C5A C14A 117.47(19) . . ?
C4A C5A C6A 124.1(2) . . ?
C14A C5A C6A 118.41(19) . . ?
C7A C6A C11A 118.2(2) . . ?
C7A C6A C5A 121.9(2) . . ?
C11A C6A C5A 119.8(2) . . ?
C8A C7A C6A 121.6(2) . . ?
C8A C7A H7A 119.2 . . ?
C6A C7A H7A 119.2 . . ?
C7A C8A C9A 119.9(2) . . ?
C7A C8A H8A 120.1 . . ?
C9A C8A H8A 120.1 . . ?
C10A C9A C8A 120.2(2) . . ?
C10A C9A H9A 119.9 . . ?
C8A C9A H9A 119.9 . . ?
C9A C10A C11A 121.4(2) . . ?
C9A C10A H10A 119.3 . . ?
C11A C10A H10A 119.3 . . ?
C10A C11A C6A 118.6(2) . . ?
C10A C11A C12A 121.7(2) . . ?
C6A C11A C12A 119.7(2) . . ?
C13A C12A C11A 119.4(2) . . ?
C13A C12A C16A 118.4(2) . . ?
C11A C12A C16A 122.1(2) . . ?
C12A C13A C14A 122.6(2) . . ?
C12A C13A H13A 118.7 . . ?
C14A C13A H13A 118.7 . . ?
C1A C14A C5A 120.0(2) . . ?
C1A C14A C13A 120.3(2) . . ?
C5A C14A C13A 119.77(19) . . ?
C16A C15A C28A 122.7(2) . . ?
C16A C15A H15A 118.7 . . ?
C28A C15A H15A 118.7 . . ?
C15A C16A C17A 119.4(2) . . ?
C15A C16A C12A 118.7(2) . . ?
C17A C16A C12A 121.8(2) . . ?
C18A C17A C22A 118.6(2) . . ?
C18A C17A C16A 121.7(2) . . ?
C22A C17A C16A 119.7(2) . . ?
C19A C18A C17A 121.0(2) . . ?
C19A C18A H18A 119.5 . . ?
C17A C18A H18A 119.5 . . ?
C18A C19A C20A 120.5(2) . . ?
C18A C19A H19A 119.7 . . ?
C20A C19A H19A 119.7 . . ?
C21A C20A C19A 120.1(2) . . ?
C21A C20A H20A 120.0 . . ?
C19A C20A H20A 120.0 . . ?
C20A C21A C22A 120.9(2) . . ?
C20A C21A H21A 119.5 . . ?
C22A C21A H21A 119.5 . . ?
C21A C22A C17A 118.7(2) . . ?
C21A C22A C23A 121.6(2) . . ?
C17A C22A C23A 119.7(2) . . ?
C24A C23A C28A 117.1(2) . . ?
C24A C23A C22A 124.2(2) . . ?
C28A C23A C22A 118.6(2) . . ?
C25A C24A C23A 122.2(2) . . ?
C25A C24A H24A 118.9 . . ?
C23A C24A H24A 118.9 . . ?
C24A C25A C26A 121.1(2) . . ?
C24A C25A H25A 119.5 . . ?
C26A C25A H25A 119.5 . . ?
C27A C26A C25A 117.6(2) . . ?
C27A C26A C30A 120.9(2) . . ?
C25A C26A C30A 121.6(2) . . ?
C26A C27A C28A 122.0(2) . . ?
C26A C27A H27A 119.0 . . ?
C28A C27A H27A 119.0 . . ?
C27A C28A C23A 119.9(2) . . ?
C27A C28A C15A 120.6(2) . . ?
C23A C28A C15A 119.5(2) . . ?
C30A C29A C42A 121.8(2) . . ?
C30A C29A H29A 119.1 . . ?
C42A C29A H29A 119.1 . . ?
C29A C30A C31A 117.5(2) . . ?
C29A C30A C26A 120.9(2) . . ?
C31A C30A C26A 121.6(2) . . ?
C32A C31A C30A 121.0(2) . . ?
C32A C31A H31A 119.5 . . ?
C30A C31A H31A 119.5 . . ?
C31A C32A C33A 122.2(2) . . ?
C31A C32A H32A 118.9 . . ?
C33A C32A H32A 118.9 . . ?
C32A C33A C42A 117.2(2) . . ?
C32A C33A C34A 124.2(2) . . ?
C42A C33A C34A 118.6(2) . . ?
C35A C34A C39A 118.4(2) . . ?
C35A C34A C33A 121.4(2) . . ?
C39A C34A C33A 120.2(2) . . ?
C36A C35A C34A 121.2(2) . . ?
C36A C35A H35A 119.4 . . ?
C34A C35A H35A 119.4 . . ?
C35A C36A C37A 120.2(2) . . ?
C35A C36A H36A 119.9 . . ?
C37A C36A H36A 119.9 . . ?
C38A C37A C36A 120.0(2) . . ?
C38A C37A H37A 120.0 . . ?
C36A C37A H37A 120.0 . . ?
C37A C38A C39A 121.3(2) . . ?
C37A C38A H38A 119.3 . . ?
C39A C38A H38A 119.3 . . ?
C38A C39A C34A 118.9(2) . . ?
C38A C39A C40A 121.8(2) . . ?
C34A C39A C40A 119.3(2) . . ?
C41A C40A C39A 119.4(2) . . ?
C41A C40A C44A 118.2(2) . . ?
C39A C40A C44A 122.4(2) . . ?
C40A C41A C42A 123.1(2) . . ?
C40A C41A H41A 118.4 . . ?
C42A C41A H41A 118.4 . . ?
C29A C42A C33A 120.2(2) . . ?
C29A C42A C41A 120.5(2) . . ?
C33A C42A C41A 119.3(2) . . ?
C44A C43A C56A 122.4(2) . . ?
C44A C43A H43A 118.8 . . ?
C56A C43A H43A 118.8 . . ?
C43A C44A C45A 119.4(2) . . ?
C43A C44A C40A 118.1(2) . . ?
C45A C44A C40A 122.35(19) . . ?
C46A C45A C50A 118.7(2) . . ?
C46A C45A C44A 121.6(2) . . ?
C50A C45A C44A 119.6(2) . . ?
C47A C46A C45A 121.3(2) . . ?
C47A C46A H46A 119.4 . . ?
C45A C46A H46A 119.4 . . ?
C46A C47A C48A 120.1(2) . . ?
C46A C47A H47A 119.9 . . ?
C48A C47A H47A 119.9 . . ?
C49A C48A C47A 120.0(2) . . ?
C49A C48A H48A 120.0 . . ?
C47A C48A H48A 120.0 . . ?
C48A C49A C50A 121.5(2) . . ?
C48A C49A H49A 119.3 . . ?
C50A C49A H49A 119.3 . . ?
C49A C50A C45A 118.2(2) . . ?
C49A C50A C51A 121.9(2) . . ?
C45A C50A C51A 119.9(2) . . ?
C52A C51A C56A 118.0(2) . . ?
C52A C51A C50A 123.5(2) . . ?
C56A C51A C50A 118.54(19) . . ?
C53A C52A C51A 121.3(2) . . ?
C53A C52A H52A 119.4 . . ?
C51A C52A H52A 119.4 . . ?
C52A C53A C54A 121.3(2) . . ?
C52A C53A H53A 119.4 . . ?
C54A C53A H53A 119.4 . . ?
C55A C54A C53A 117.9(2) . . ?
C55A C54A C58A 120.8(2) . . ?
C53A C54A C58A 121.4(2) . . ?
C54A C55A C56A 121.6(2) . . ?
C54A C55A H55A 119.2 . . ?
C56A C55A H55A 119.2 . . ?
C51A C56A C55A 119.8(2) . . ?
C51A C56A C43A 119.8(2) . . ?
C55A C56A C43A 120.4(2) . . ?
C58A C57A C70A 121.6(2) . . ?
C58A C57A H57A 119.2 . . ?
C70A C57A H57A 119.2 . . ?
C57A C58A C59A 117.8(2) . . ?
C57A C58A C54A 120.5(2) . . ?
C59A C58A C54A 121.8(2) . . ?
C60A C59A C58A 121.5(2) . . ?
C60A C59A H59A 119.2 . . ?
C58A C59A H59A 119.2 . . ?
C59A C60A C61A 121.5(2) . . ?
C59A C60A H60A 119.3 . . ?
C61A C60A H60A 119.3 . . ?
C60A C61A C70A 117.3(2) . . ?
C60A C61A C62A 124.5(2) . . ?
C70A C61A C62A 118.3(2) . . ?
C63A C62A C67A 118.5(2) . . ?
C63A C62A C61A 121.2(2) . . ?
C67A C62A C61A 120.3(2) . . ?
C64A C63A C62A 121.3(2) . . ?
C64A C63A H63A 119.3 . . ?
C62A C63A H63A 119.3 . . ?
C63A C64A C65A 120.2(2) . . ?
C63A C64A H64A 119.9 . . ?
C65A C64A H64A 119.9 . . ?
C66A C65A C64A 119.6(2) . . ?
C66A C65A H65A 120.2 . . ?
C64A C65A H65A 120.2 . . ?
C65A C66A C67A 121.5(2) . . ?
C65A C66A H66A 119.2 . . ?
C67A C66A H66A 119.2 . . ?
C66A C67A C62A 118.9(2) . . ?
C66A C67A C68A 121.7(2) . . ?
C62A C67A C68A 119.4(2) . . ?
C69A C68A C67A 119.2(2) . . ?
C69A C68A C72A 118.0(2) . . ?
C67A C68A C72A 122.7(2) . . ?
C68A C69A C70A 123.1(2) . . ?
C68A C69A H69A 118.5 . . ?
C70A C69A H69A 118.5 . . ?
C57A C70A C61A 120.2(2) . . ?
C57A C70A C69A 120.2(2) . . ?
C61A C70A C69A 119.6(2) . . ?
C72A C71A C84A 122.6(2) . . ?
C72A C71A H71A 118.7 . . ?
C84A C71A H71A 118.7 . . ?
C71A C72A C73A 119.1(2) . . ?
C71A C72A C68A 117.9(2) . . ?
C73A C72A C68A 122.78(19) . . ?
C74A C73A C78A 119.0(2) . . ?
C74A C73A C72A 121.3(2) . . ?
C78A C73A C72A 119.7(2) . . ?
C75A C74A C73A 121.1(2) . . ?
C75A C74A H74A 119.5 . . ?
C73A C74A H74A 119.5 . . ?
C74A C75A C76A 120.1(2) . . ?
C74A C75A H75A 119.9 . . ?
C76A C75A H75A 119.9 . . ?
C77A C76A C75A 120.2(2) . . ?
C77A C76A H76A 119.9 . . ?
C75A C76A H76A 119.9 . . ?
C76A C77A C78A 121.2(2) . . ?
C76A C77A H77A 119.4 . . ?
C78A C77A H77A 119.4 . . ?
C73A C78A C77A 118.3(2) . . ?
C73A C78A C79A 119.9(2) . . ?
C77A C78A C79A 121.6(2) . . ?
C80A C79A C84A 117.6(2) . . ?
C80A C79A C78A 123.6(2) . . ?
C84A C79A C78A 118.8(2) . . ?
C81A C80A C79A 121.3(2) . . ?
C81A C80A H80A 119.3 . . ?
C79A C80A H80A 119.3 . . ?
C80A C81A C82A 121.2(2) . . ?
C80A C81A H81A 119.4 . . ?
C82A C81A H81A 119.4 . . ?
C83A C82A C81A 118.1(2) . . ?
C83A C82A C2A 121.3(2) . . ?
C81A C82A C2A 120.7(2) . . ?
C82A C83A C84A 121.7(2) . . ?
C82A C83A H83A 119.2 . . ?
C84A C83A H83A 119.2 . . ?
C83A C84A C79A 120.0(2) . . ?
C83A C84A C71A 120.7(2) . . ?
C79A C84A C71A 119.34(19) . . ?
C6Y C1Y C2Y 106.2(12) . . ?
C6Y C1Y Cl1Y 106.4(13) . . ?
C2Y C1Y Cl1Y 147.4(16) . . ?
C3Y C2Y C1Y 130.8(13) . . ?
C3Y C2Y Cl2Y 112.2(12) . . ?
C1Y C2Y Cl2Y 116.9(13) . . ?
C4Y C3Y C2Y 109.1(13) . . ?
C4Y C3Y H3Y 125.5 . . ?
C2Y C3Y H3Y 125.5 . . ?
C3Y C4Y C5Y 131.7(14) . . ?
C3Y C4Y Cl4Y 93.7(11) . . ?
C5Y C4Y Cl4Y 132.4(15) . . ?
C4Y C5Y C6Y 110.2(15) . . ?
C4Y C5Y H5Y 124.9 . . ?
C6Y C5Y H5Y 124.9 . . ?
C5Y C6Y C1Y 130.1(16) . . ?
C5Y C6Y H6Y 115.0 . . ?
C1Y C6Y H6Y 115.0 . . ?
C2Z C1Z C6Z 113.9(8) . . ?
C2Z C1Z Cl1Z 136.3(8) . . ?
C6Z C1Z Cl1Z 109.8(7) . . ?
C3Z C2Z C1Z 126.2(8) . . ?
C3Z C2Z Cl2Z 116.3(6) . . ?
C1Z C2Z Cl2Z 117.5(7) . . ?
C4Z C3Z C2Z 113.4(7) . . ?
C4Z C3Z H3Z 123.3 . . ?
C2Z C3Z H3Z 123.3 . . ?
C5Z C4Z C3Z 127.9(7) . . ?
C5Z C4Z Cl4Z 127.5(7) . . ?
C3Z C4Z Cl4Z 104.6(8) . . ?
C4Z C5Z C6Z 114.8(8) . . ?
C4Z C5Z H5Z 122.6 . . ?
C6Z C5Z H5Z 122.6 . . ?
C5Z C6Z C1Z 123.6(8) . . ?
C5Z C6Z H6Z 118.2 . . ?
C1Z C6Z H6Z 118.2 . . ?

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
C14A C1A C2A C3A 1.7(3) . . . . ?
C14A C1A C2A C82A -178.1(2) . . . . ?
C1A C2A C3A C4A -2.6(4) . . . . ?
C82A C2A C3A C4A 177.2(2) . . . . ?
C2A C3A C4A C5A 0.8(4) . . . . ?
C3A C4A C5A C14A 1.9(3) . . . . ?
C3A C4A C5A C6A -175.8(2) . . . . ?
C4A C5A C6A C7A 1.5(4) . . . . ?
C14A C5A C6A C7A -176.1(2) . . . . ?
C4A C5A C6A C11A 178.6(2) . . . . ?
C14A C5A C6A C11A 0.9(3) . . . . ?
C11A C6A C7A C8A -2.3(4) . . . . ?
C5A C6A C7A C8A 174.8(2) . . . . ?
C6A C7A C8A C9A -1.2(4) . . . . ?
C7A C8A C9A C10A 2.8(5) . . . . ?
C8A C9A C10A C11A -0.9(5) . . . . ?
C9A C10A C11A C6A -2.6(4) . . . . ?
C9A C10A C11A C12A 179.9(3) . . . . ?
C7A C6A C11A C10A 4.1(4) . . . . ?
C5A C6A C11A C10A -173.0(2) . . . . ?
C7A C6A C11A C12A -178.3(2) . . . . ?
C5A C6A C11A C12A 4.5(3) . . . . ?
C10A C11A C12A C13A 171.5(2) . . . . ?
C6A C11A C12A C13A -5.9(4) . . . . ?
C10A C11A C12A C16A -5.1(4) . . . . ?
C6A C11A C12A C16A 177.4(2) . . . . ?
C11A C12A C13A C14A 1.8(4) . . . . ?
C16A C12A C13A C14A 178.6(2) . . . . ?
C2A C1A C14A C5A 1.0(4) . . . . ?
C2A C1A C14A C13A -178.9(2) . . . . ?
C4A C5A C14A C1A -2.8(3) . . . . ?
C6A C5A C14A C1A 175.0(2) . . . . ?
C4A C5A C14A C13A 177.1(2) . . . . ?
C6A C5A C14A C13A -5.0(3) . . . . ?
C12A C13A C14A C1A -176.3(2) . . . . ?
C12A C13A C14A C5A 3.8(4) . . . . ?
C28A C15A C16A C17A 1.2(4) . . . . ?
C28A C15A C16A C12A 177.2(2) . . . . ?
C13A C12A C16A C15A -51.5(3) . . . . ?
C11A C12A C16A C15A 125.2(3) . . . . ?
C13A C12A C16A C17A 124.4(3) . . . . ?
C11A C12A C16A C17A -58.9(3) . . . . ?
C15A C16A C17A C18A 171.7(2) . . . . ?
C12A C16A C17A C18A -4.2(4) . . . . ?
C15A C16A C17A C22A -5.6(4) . . . . ?
C12A C16A C17A C22A 178.5(2) . . . . ?
C22A C17A C18A C19A -3.2(4) . . . . ?
C16A C17A C18A C19A 179.5(3) . . . . ?
C17A C18A C19A C20A -0.4(4) . . . . ?
C18A C19A C20A C21A 2.4(4) . . . . ?
C19A C20A C21A C22A -0.6(4) . . . . ?
C20A C21A C22A C17A -3.0(4) . . . . ?
C20A C21A C22A C23A 174.4(2) . . . . ?
C18A C17A C22A C21A 4.8(4) . . . . ?
C16A C17A C22A C21A -177.8(2) . . . . ?
C18A C17A C22A C23A -172.6(2) . . . . ?
C16A C17A C22A C23A 4.7(3) . . . . ?
C21A C22A C23A C24A 0.6(4) . . . . ?
C17A C22A C23A C24A 178.0(2) . . . . ?
C21A C22A C23A C28A -176.9(2) . . . . ?
C17A C22A C23A C28A 0.5(3) . . . . ?
C28A C23A C24A C25A 2.0(3) . . . . ?
C22A C23A C24A C25A -175.5(2) . . . . ?
C23A C24A C25A C26A 1.4(4) . . . . ?
C24A C25A C26A C27A -3.4(4) . . . . ?
C24A C25A C26A C30A 176.5(2) . . . . ?
C25A C26A C27A C28A 2.0(3) . . . . ?
C30A C26A C27A C28A -177.8(2) . . . . ?
C26A C27A C28A C23A 1.3(4) . . . . ?
C26A C27A C28A C15A -179.5(2) . . . . ?
C24A C23A C28A C27A -3.4(3) . . . . ?
C22A C23A C28A C27A 174.3(2) . . . . ?
C24A C23A C28A C15A 177.5(2) . . . . ?
C22A C23A C28A C15A -4.8(3) . . . . ?
C16A C15A C28A C27A -175.1(2) . . . . ?
C16A C15A C28A C23A 4.1(4) . . . . ?
C42A C29A C30A C31A 0.9(3) . . . . ?
C42A C29A C30A C26A -179.2(2) . . . . ?
C27A C26A C30A C29A 44.0(3) . . . . ?
C25A C26A C30A C29A -135.9(2) . . . . ?
C27A C26A C30A C31A -136.1(2) . . . . ?
C25A C26A C30A C31A 44.1(3) . . . . ?
C29A C30A C31A C32A -2.8(4) . . . . ?
C26A C30A C31A C32A 177.3(2) . . . . ?
C30A C31A C32A C33A 1.7(4) . . . . ?
C31A C32A C33A C42A 1.3(4) . . . . ?
C31A C32A C33A C34A -177.5(2) . . . . ?
C32A C33A C34A C35A 3.4(4) . . . . ?
C42A C33A C34A C35A -175.3(2) . . . . ?
C32A C33A C34A C39A -178.5(2) . . . . ?
C42A C33A C34A C39A 2.8(3) . . . . ?
C39A C34A C35A C36A -0.7(4) . . . . ?
C33A C34A C35A C36A 177.5(2) . . . . ?
C34A C35A C36A C37A -0.2(4) . . . . ?
C35A C36A C37A C38A 0.2(4) . . . . ?
C36A C37A C38A C39A 0.7(4) . . . . ?
C37A C38A C39A C34A -1.6(4) . . . . ?
C37A C38A C39A C40A -179.5(2) . . . . ?
C35A C34A C39A C38A 1.5(3) . . . . ?
C33A C34A C39A C38A -176.6(2) . . . . ?
C35A C34A C39A C40A 179.5(2) . . . . ?
C33A C34A C39A C40A 1.4(3) . . . . ?
C38A C39A C40A C41A 174.2(2) . . . . ?
C34A C39A C40A C41A -3.7(3) . . . . ?
C38A C39A C40A C44A -1.6(4) . . . . ?
C34A C39A C40A C44A -179.5(2) . . . . ?
C39A C40A C41A C42A 1.8(4) . . . . ?
C44A C40A C41A C42A 177.8(2) . . . . ?
C30A C29A C42A C33A 2.1(4) . . . . ?
C30A C29A C42A C41A -177.6(2) . . . . ?
C32A C33A C42A C29A -3.2(3) . . . . ?
C34A C33A C42A C29A 175.7(2) . . . . ?
C32A C33A C42A C41A 176.5(2) . . . . ?
C34A C33A C42A C41A -4.6(3) . . . . ?
C40A C41A C42A C29A -177.9(2) . . . . ?
C40A C41A C42A C33A 2.4(4) . . . . ?
C56A C43A C44A C45A 2.3(4) . . . . ?
C56A C43A C44A C40A 177.4(2) . . . . ?
C41A C40A C44A C43A -52.4(3) . . . . ?
C39A C40A C44A C43A 123.4(3) . . . . ?
C41A C40A C44A C45A 122.5(3) . . . . ?
C39A C40A C44A C45A -61.6(3) . . . . ?
C43A C44A C45A C46A 170.6(2) . . . . ?
C40A C44A C45A C46A -4.2(4) . . . . ?
C43A C44A C45A C50A -6.0(3) . . . . ?
C40A C44A C45A C50A 179.1(2) . . . . ?
C50A C45A C46A C47A -2.0(4) . . . . ?
C44A C45A C46A C47A -178.7(2) . . . . ?
C45A C46A C47A C48A -0.8(4) . . . . ?
C46A C47A C48A C49A 1.5(4) . . . . ?
C47A C48A C49A C50A 0.8(4) . . . . ?
C48A C49A C50A C45A -3.6(4) . . . . ?
C48A C49A C50A C51A 173.7(2) . . . . ?
C46A C45A C50A C49A 4.2(3) . . . . ?
C44A C45A C50A C49A -179.1(2) . . . . ?
C46A C45A C50A C51A -173.3(2) . . . . ?
C44A C45A C50A C51A 3.5(3) . . . . ?
C49A C50A C51A C52A 3.4(4) . . . . ?
C45A C50A C51A C52A -179.2(2) . . . . ?
C49A C50A C51A C56A -174.6(2) . . . . ?
C45A C50A C51A C56A 2.7(3) . . . . ?
C56A C51A C52A C53A 2.8(3) . . . . ?
C50A C51A C52A C53A -175.3(2) . . . . ?
C51A C52A C53A C54A 1.4(4) . . . . ?
C52A C53A C54A C55A -3.8(3) . . . . ?
C52A C53A C54A C58A 175.2(2) . . . . ?
C53A C54A C55A C56A 2.2(3) . . . . ?
C58A C54A C55A C56A -176.9(2) . . . . ?
C52A C51A C56A C55A -4.4(3) . . . . ?
C50A C51A C56A C55A 173.8(2) . . . . ?
C52A C51A C56A C43A 175.4(2) . . . . ?
C50A C51A C56A C43A -6.4(3) . . . . ?
C54A C55A C56A C51A 2.0(4) . . . . ?
C54A C55A C56A C43A -177.8(2) . . . . ?
C44A C43A C56A C51A 4.1(4) . . . . ?
C44A C43A C56A C55A -176.2(2) . . . . ?
C70A C57A C58A C59A 1.5(3) . . . . ?
C70A C57A C58A C54A -178.9(2) . . . . ?
C55A C54A C58A C57A 46.3(3) . . . . ?
C53A C54A C58A C57A -132.7(2) . . . . ?
C55A C54A C58A C59A -134.1(2) . . . . ?
C53A C54A C58A C59A 46.9(3) . . . . ?
C57A C58A C59A C60A -3.2(3) . . . . ?
C54A C58A C59A C60A 177.2(2) . . . . ?
C58A C59A C60A C61A 1.7(4) . . . . ?
C59A C60A C61A C70A 1.4(3) . . . . ?
C59A C60A C61A C62A -177.7(2) . . . . ?
C60A C61A C62A C63A 4.2(4) . . . . ?
C70A C61A C62A C63A -175.0(2) . . . . ?
C60A C61A C62A C67A -177.9(2) . . . . ?
C70A C61A C62A C67A 3.0(3) . . . . ?
C67A C62A C63A C64A -0.1(4) . . . . ?
C61A C62A C63A C64A 177.9(2) . . . . ?
C62A C63A C64A C65A -0.2(4) . . . . ?
C63A C64A C65A C66A -0.4(4) . . . . ?
C64A C65A C66A C67A 1.4(4) . . . . ?
C65A C66A C67A C62A -1.7(4) . . . . ?
C65A C66A C67A C68A -179.5(2) . . . . ?
C63A C62A C67A C66A 1.0(3) . . . . ?
C61A C62A C67A C66A -177.0(2) . . . . ?
C63A C62A C67A C68A 178.9(2) . . . . ?
C61A C62A C67A C68A 0.9(3) . . . . ?
C66A C67A C68A C69A 174.7(2) . . . . ?
C62A C67A C68A C69A -3.2(3) . . . . ?
C66A C67A C68A C72A -1.9(4) . . . . ?
C62A C67A C68A C72A -179.7(2) . . . . ?
C67A C68A C69A C70A 1.7(4) . . . . ?
C72A C68A C69A C70A 178.3(2) . . . . ?
C58A C57A C70A C61A 1.7(3) . . . . ?
C58A C57A C70A C69A -177.7(2) . . . . ?
C60A C61A C70A C57A -3.1(3) . . . . ?
C62A C61A C70A C57A 176.1(2) . . . . ?
C60A C61A C70A C69A 176.3(2) . . . . ?
C62A C61A C70A C69A -4.5(3) . . . . ?
C68A C69A C70A C57A -178.3(2) . . . . ?
C68A C69A C70A C61A 2.2(4) . . . . ?
C84A C71A C72A C73A 2.8(3) . . . . ?
C84A C71A C72A C68A 177.0(2) . . . . ?
C69A C68A C72A C71A -52.2(3) . . . . ?
C67A C68A C72A C71A 124.4(2) . . . . ?
C69A C68A C72A C73A 121.8(2) . . . . ?
C67A C68A C72A C73A -61.6(3) . . . . ?
C71A C72A C73A C74A 170.4(2) . . . . ?
C68A C72A C73A C74A -3.5(3) . . . . ?
C71A C72A C73A C78A -6.9(3) . . . . ?
C68A C72A C73A C78A 179.2(2) . . . . ?
C78A C73A C74A C75A -1.8(4) . . . . ?
C72A C73A C74A C75A -179.1(2) . . . . ?
C73A C74A C75A C76A -0.9(4) . . . . ?
C74A C75A C76A C77A 2.0(4) . . . . ?
C75A C76A C77A C78A -0.4(4) . . . . ?
C74A C73A C78A C77A 3.4(3) . . . . ?
C72A C73A C78A C77A -179.3(2) . . . . ?
C74A C73A C78A C79A -173.1(2) . . . . ?
C72A C73A C78A C79A 4.2(3) . . . . ?
C76A C77A C78A C73A -2.3(3) . . . . ?
C76A C77A C78A C79A 174.1(2) . . . . ?
C73A C78A C79A C80A 179.9(2) . . . . ?
C77A C78A C79A C80A 3.6(3) . . . . ?
C73A C78A C79A C84A 2.5(3) . . . . ?
C77A C78A C79A C84A -173.9(2) . . . . ?
C84A C79A C80A C81A 2.4(3) . . . . ?
C78A C79A C80A C81A -175.1(2) . . . . ?
C79A C80A C81A C82A 1.3(4) . . . . ?
C80A C81A C82A C83A -3.3(3) . . . . ?
C80A C81A C82A C2A 176.1(2) . . . . ?
C1A C2A C82A C83A 44.1(3) . . . . ?
C3A C2A C82A C83A -135.7(2) . . . . ?
C1A C2A C82A C81A -135.3(2) . . . . ?
C3A C2A C82A C81A 44.9(3) . . . . ?
C81A C82A C83A C84A 1.5(3) . . . . ?
C2A C82A C83A C84A -177.8(2) . . . . ?
C82A C83A C84A C79A 2.2(3) . . . . ?
C82A C83A C84A C71A -177.7(2) . . . . ?
C80A C79A C84A C83A -4.1(3) . . . . ?
C78A C79A C84A C83A 173.5(2) . . . . ?
C80A C79A C84A C71A 175.8(2) . . . . ?
C78A C79A C84A C71A -6.6(3) . . . . ?
C72A C71A C84A C83A -176.1(2) . . . . ?
C72A C71A C84A C79A 4.0(3) . . . . ?
C6Y C1Y C2Y C3Y 3(4) . . . . ?
Cl1Y C1Y C2Y C3Y -174(4) . . . . ?
C6Y C1Y C2Y Cl2Y -178.9(18) . . . . ?
Cl1Y C1Y C2Y Cl2Y 4(6) . . . . ?
C1Y C2Y C3Y C4Y 5(3) . . . . ?
Cl2Y C2Y C3Y C4Y -173.7(19) . . . . ?
C2Y C3Y C4Y C5Y -16(4) . . . . ?
C2Y C3Y C4Y Cl4Y 179.7(14) . . . . ?
C3Y C4Y C5Y C6Y 17(4) . . . . ?
Cl4Y C4Y C5Y C6Y 175(2) . . . . ?
C4Y C5Y C6Y C1Y -6(3) . . . . ?
C2Y C1Y C6Y C5Y -2(4) . . . . ?
Cl1Y C1Y C6Y C5Y 176.2(15) . . . . ?
C6Z C1Z C2Z C3Z 4.9(18) . . . . ?
Cl1Z C1Z C2Z C3Z -178.9(11) . . . . ?
C6Z C1Z C2Z Cl2Z -176.1(8) . . . . ?
Cl1Z C1Z C2Z Cl2Z 0(2) . . . . ?
C1Z C2Z C3Z C4Z -1.2(16) . . . . ?
Cl2Z C2Z C3Z C4Z 179.8(11) . . . . ?
C2Z C3Z C4Z C5Z -3(2) . . . . ?
C2Z C3Z C4Z Cl4Z 178.5(8) . . . . ?
C3Z C4Z C5Z C6Z 3(2) . . . . ?
Cl4Z C4Z C5Z C6Z -179.1(12) . . . . ?
C4Z C5Z C6Z C1Z 1.3(15) . . . . ?
C2Z C1Z C6Z C5Z -4.9(17) . . . . ?
Cl1Z C1Z C6Z C5Z 177.9(6) . . . . ?

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.051



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,2,4-trichlorobenzene and methanol'
####################################################################### 
# 
# 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_p21c
_database_code_depnum_ccdc_archive 'CCDC 1976912'
loop_
_audit_author_name
_audit_author_address
'Sota Sato'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2020-01-11 deposited with the CCDC.	2020-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C56 H32'
_chemical_formula_sum            'C56 H32'
_chemical_formula_weight         704.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0038 0.0019 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.6620(16)
_cell_length_b                   15.9490(11)
_cell_length_c                   14.374(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.232(4)
_cell_angle_gamma                90
_cell_volume                     1733.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14363
_cell_measurement_theta_min      2.054
_cell_measurement_theta_max      27.210

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'XDS (Kabsch, 2010)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.760
_diffrn_radiation_type           synchrotron
_diffrn_source                   'SPring-8 BL38B1 bending magnet beamline'
_diffrn_measurement_device_type  'PAD Pilatus3 6M (Dectris)'
_diffrn_measurement_method       'oscillation method, ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40355
_diffrn_reflns_av_unetI/netI     0.0084
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.054
_diffrn_reflns_theta_max         27.210
_diffrn_reflns_theta_full        27.129
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3157
_reflns_number_gt                2983
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'SPring-8 BSS'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'SHELXT-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0606P)²+0.8747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3157
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.23085(19) 0.62055(9) 0.66822(10) 0.0297(3) Uani 1 1 d . . . . .
H1 H -0.291730 0.627059 0.605660 0.036 Uiso 1 1 calc R U . . .
C2 C -0.29516(19) 0.56499(10) 0.72581(10) 0.0290(3) Uani 1 1 d . . . . .
C3 C -0.23270(19) 0.57162(9) 0.82682(10) 0.0293(3) Uani 1 1 d . . . . .
C4 C -0.3062(2) 0.52416(10) 0.89351(11) 0.0330(3) Uani 1 1 d . . . . .
H4 H -0.394862 0.483800 0.872298 0.040 Uiso 1 1 calc R U . . .
C5 C -0.2521(2) 0.53503(10) 0.98911(11) 0.0354(4) Uani 1 1 d . . . . .
H5 H -0.306406 0.503919 1.033026 0.043 Uiso 1 1 calc R U . . .
C6 C -0.1174(2) 0.59181(10) 1.02091(10) 0.0353(4) Uani 1 1 d . . . . .
H6 H -0.082222 0.600605 1.086607 0.042 Uiso 1 1 calc R U . . .
C7 C -0.0357(2) 0.63497(10) 0.95757(10) 0.0319(3) Uani 1 1 d . . . . .
H7 H 0.059747 0.671406 0.980322 0.038 Uiso 1 1 calc R U . . .
C8 C -0.0894(2) 0.62672(9) 0.85976(10) 0.0295(3) Uani 1 1 d . . . . .
C9 C 0.0037(2) 0.66947(9) 0.79280(10) 0.0290(3) Uani 1 1 d . . . . .
C10 C 0.1752(2) 0.70325(10) 0.81460(10) 0.0312(3) Uani 1 1 d . . . . .
H10 H 0.226494 0.710700 0.878747 0.037 Uiso 1 1 calc R U . . .
C11 C 0.2708(2) 0.72589(10) 0.74423(10) 0.0316(3) Uani 1 1 d . . . . .
H11 H 0.387932 0.746522 0.760799 0.038 Uiso 1 1 calc R U . . .
C12 C 0.1956(2) 0.71856(9) 0.64847(10) 0.0303(3) Uani 1 1 d . . . . .
C13 C 0.0180(2) 0.69839(9) 0.62809(10) 0.0302(3) Uani 1 1 d . . . . .
H13 H -0.041766 0.704319 0.565209 0.036 Uiso 1 1 calc R U . . .
C14 C -0.07621(19) 0.66955(9) 0.69737(10) 0.0291(3) Uani 1 1 d . . . . .
C15 C 0.2551(2) 0.64113(10) 0.51270(10) 0.0322(3) Uani 1 1 d . . . . .
H15 H 0.151790 0.610534 0.520002 0.039 Uiso 1 1 calc R U . . .
C16 C 0.3026(2) 0.70787(10) 0.57092(10) 0.0309(3) Uani 1 1 d . . . . .
C17 C 0.4526(2) 0.75465(10) 0.55540(10) 0.0321(3) Uani 1 1 d . . . . .
H17 H 0.486876 0.802854 0.592711 0.039 Uiso 1 1 calc R U . . .
C18 C 0.5496(2) 0.73077(10) 0.48636(10) 0.0318(3) Uani 1 1 d . . . . .
H18 H 0.648091 0.763857 0.476439 0.038 Uiso 1 1 calc R U . . .
C19 C 0.50625(19) 0.65834(9) 0.43001(10) 0.0291(3) Uani 1 1 d . . . . .
C20 C 0.61198(19) 0.62148(10) 0.36482(10) 0.0296(3) Uani 1 1 d . . . . .
C21 C 0.7747(2) 0.65609(10) 0.35123(11) 0.0329(3) Uani 1 1 d . . . . .
H21 H 0.811125 0.708206 0.379972 0.039 Uiso 1 1 calc R U . . .
C22 C 0.8823(2) 0.61635(11) 0.29741(11) 0.0361(4) Uani 1 1 d . . . . .
H22 H 0.990565 0.641602 0.288261 0.043 Uiso 1 1 calc R U . . .
C23 C 0.8329(2) 0.53878(11) 0.25601(11) 0.0351(4) Uani 1 1 d . . . . .
H23 H 0.910949 0.509727 0.222171 0.042 Uiso 1 1 calc R U . . .
C24 C 0.6731(2) 0.50490(10) 0.26418(10) 0.0321(3) Uani 1 1 d . . . . .
H24 H 0.639682 0.452787 0.234563 0.039 Uiso 1 1 calc R U . . .
C25 C 0.55581(19) 0.54567(9) 0.31582(10) 0.0294(3) Uani 1 1 d . . . . .
C26 C 0.38541(19) 0.50981(10) 0.32381(10) 0.0293(3) Uani 1 1 d . . . . .
C27 C 0.2926(2) 0.54494(10) 0.38663(10) 0.0313(3) Uani 1 1 d . . . . .
H27 H 0.181922 0.520832 0.393385 0.038 Uiso 1 1 calc R U . . .
C28 C 0.3517(2) 0.61579(10) 0.44282(10) 0.0303(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.358(2) . ?
C1 C14 1.425(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.458(2) . ?
C2 C26 1.501(2) 3_566 ?
C3 C4 1.408(2) . ?
C3 C8 1.426(2) . ?
C4 C5 1.381(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.370(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.406(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.457(2) . ?
C9 C10 1.408(2) . ?
C9 C14 1.410(2) . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.409(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(2) . ?
C12 C16 1.496(2) . ?
C13 C14 1.398(2) . ?
C13 H13 0.9500 . ?
C15 C16 1.367(2) . ?
C15 C28 1.400(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.417(2) . ?
C17 C18 1.386(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.419(2) . ?
C18 H18 0.9500 . ?
C19 C28 1.402(2) . ?
C19 C20 1.457(2) . ?
C20 C21 1.406(2) . ?
C20 C25 1.430(2) . ?
C21 C22 1.373(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.398(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.361(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.412(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.447(2) . ?
C26 C27 1.357(2) . ?
C27 C28 1.420(2) . ?
C27 H27 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C14 122.99(13) . . ?
C2 C1 H1 118.5 . . ?
C14 C1 H1 118.5 . . ?
C1 C2 C3 117.81(14) . . ?
C1 C2 C26 114.43(13) . 3_566 ?
C3 C2 C26 125.71(13) . 3_566 ?
C4 C3 C8 118.41(13) . . ?
C4 C3 C2 122.40(14) . . ?
C8 C3 C2 119.18(13) . . ?
C5 C4 C3 121.39(15) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 119.75(14) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 120.11(14) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 121.69(15) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C3 118.42(14) . . ?
C7 C8 C9 121.38(14) . . ?
C3 C8 C9 120.12(13) . . ?
C10 C9 C14 117.42(13) . . ?
C10 C9 C8 124.81(13) . . ?
C14 C9 C8 117.45(13) . . ?
C11 C10 C9 121.31(14) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 120.63(14) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 117.39(13) . . ?
C13 C12 C16 117.00(13) . . ?
C11 C12 C16 123.41(14) . . ?
C12 C13 C14 121.89(13) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C9 120.01(14) . . ?
C13 C14 C1 118.09(13) . . ?
C9 C14 C1 119.77(13) . . ?
C16 C15 C28 123.00(14) . . ?
C16 C15 H15 118.5 . . ?
C28 C15 H15 118.5 . . ?
C15 C16 C17 117.17(14) . . ?
C15 C16 C12 114.91(14) . . ?
C17 C16 C12 127.76(14) . . ?
C18 C17 C16 120.65(14) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 121.94(14) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C28 C19 C18 116.38(13) . . ?
C28 C19 C20 117.22(13) . . ?
C18 C19 C20 126.29(14) . . ?
C21 C20 C25 117.84(14) . . ?
C21 C20 C19 121.88(14) . . ?
C25 C20 C19 120.21(13) . . ?
C22 C21 C20 121.56(15) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C23 120.14(15) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 120.04(15) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 121.30(15) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C24 C25 C20 118.78(14) . . ?
C24 C25 C26 121.19(14) . . ?
C20 C25 C26 119.94(13) . . ?
C27 C26 C25 117.75(14) . . ?
C27 C26 C2 113.19(13) . 3_566 ?
C25 C26 C2 129.01(13) . 3_566 ?
C26 C27 C28 123.60(14) . . ?
C26 C27 H27 118.2 . . ?
C28 C27 H27 118.2 . . ?
C15 C28 C19 120.63(14) . . ?
C15 C28 C27 118.72(14) . . ?
C19 C28 C27 120.64(14) . . ?

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
C14 C1 C2 C3 16.5(2) . . . . ?
C14 C1 C2 C26 -148.11(14) . . . 3_566 ?
C1 C2 C3 C4 172.13(14) . . . . ?
C26 C2 C3 C4 -25.1(2) 3_566 . . . ?
C1 C2 C3 C8 -9.3(2) . . . . ?
C26 C2 C3 C8 153.48(14) 3_566 . . . ?
C8 C3 C4 C5 5.2(2) . . . . ?
C2 C3 C4 C5 -176.14(14) . . . . ?
C3 C4 C5 C6 -2.4(2) . . . . ?
C4 C5 C6 C7 -1.8(2) . . . . ?
C5 C6 C7 C8 3.1(2) . . . . ?
C6 C7 C8 C3 -0.1(2) . . . . ?
C6 C7 C8 C9 -176.83(14) . . . . ?
C4 C3 C8 C7 -3.9(2) . . . . ?
C2 C3 C8 C7 177.40(13) . . . . ?
C4 C3 C8 C9 172.82(13) . . . . ?
C2 C3 C8 C9 -5.8(2) . . . . ?
C7 C8 C9 C10 17.4(2) . . . . ?
C3 C8 C9 C10 -159.24(14) . . . . ?
C7 C8 C9 C14 -169.34(14) . . . . ?
C3 C8 C9 C14 14.0(2) . . . . ?
C14 C9 C10 C11 -8.0(2) . . . . ?
C8 C9 C10 C11 165.23(14) . . . . ?
C9 C10 C11 C12 2.4(2) . . . . ?
C10 C11 C12 C13 8.0(2) . . . . ?
C10 C11 C12 C16 -154.64(15) . . . . ?
C11 C12 C13 C14 -12.9(2) . . . . ?
C16 C12 C13 C14 150.86(14) . . . . ?
C12 C13 C14 C9 7.4(2) . . . . ?
C12 C13 C14 C1 -156.02(14) . . . . ?
C10 C9 C14 C13 3.3(2) . . . . ?
C8 C9 C14 C13 -170.50(13) . . . . ?
C10 C9 C14 C1 166.35(14) . . . . ?
C8 C9 C14 C1 -7.4(2) . . . . ?
C2 C1 C14 C13 155.21(15) . . . . ?
C2 C1 C14 C9 -8.2(2) . . . . ?
C28 C15 C16 C17 2.9(2) . . . . ?
C28 C15 C16 C12 -172.83(14) . . . . ?
C13 C12 C16 C15 -35.5(2) . . . . ?
C11 C12 C16 C15 127.20(16) . . . . ?
C13 C12 C16 C17 149.34(15) . . . . ?
C11 C12 C16 C17 -48.0(2) . . . . ?
C15 C16 C17 C18 -2.6(2) . . . . ?
C12 C16 C17 C18 172.52(15) . . . . ?
C16 C17 C18 C19 -1.3(2) . . . . ?
C17 C18 C19 C28 4.8(2) . . . . ?
C17 C18 C19 C20 -171.22(14) . . . . ?
C28 C19 C20 C21 -175.96(14) . . . . ?
C18 C19 C20 C21 0.0(2) . . . . ?
C28 C19 C20 C25 0.9(2) . . . . ?
C18 C19 C20 C25 176.92(14) . . . . ?
C25 C20 C21 C22 -3.9(2) . . . . ?
C19 C20 C21 C22 173.08(14) . . . . ?
C20 C21 C22 C23 -1.3(2) . . . . ?
C21 C22 C23 C24 4.0(2) . . . . ?
C22 C23 C24 C25 -1.4(2) . . . . ?
C23 C24 C25 C20 -3.8(2) . . . . ?
C23 C24 C25 C26 179.54(14) . . . . ?
C21 C20 C25 C24 6.3(2) . . . . ?
C19 C20 C25 C24 -170.72(13) . . . . ?
C21 C20 C25 C26 -176.97(13) . . . . ?
C19 C20 C25 C26 6.0(2) . . . . ?
C24 C25 C26 C27 169.43(14) . . . . ?
C20 C25 C26 C27 -7.2(2) . . . . ?
C24 C25 C26 C2 -7.9(2) . . . 3_566 ?
C20 C25 C26 C2 175.43(13) . . . 3_566 ?
C25 C26 C27 C28 1.6(2) . . . . ?
C2 C26 C27 C28 179.31(13) 3_566 . . . ?
C16 C15 C28 C19 0.7(2) . . . . ?
C16 C15 C28 C27 179.26(14) . . . . ?
C18 C19 C28 C15 -4.5(2) . . . . ?
C20 C19 C28 C15 171.90(13) . . . . ?
C18 C19 C28 C27 177.00(13) . . . . ?
C20 C19 C28 C27 -6.6(2) . . . . ?
C26 C27 C28 C15 -172.96(14) . . . . ?
C26 C27 C28 C19 5.6(2) . . . . ?

_refine_diff_density_max         0.591
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.041


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform and acetonitrile'
####################################################################### 
# 
# 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_xcalibur
_database_code_depnum_ccdc_archive 'CCDC 1977015'
loop_
_audit_author_name
_audit_author_address
'Sota Sato'
;The University of Tokyo
Japan
;
_audit_update_record             
;
2020-01-12 deposited with the CCDC.	2020-06-16 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C15 H10 Br I O2'
_chemical_formula_moiety         'C15 H10 Br I O2'
_chemical_formula_weight         429.05
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.9349(2)
_cell_length_b                   8.1555(2)
_cell_length_c                   11.7247(3)
_cell_angle_alpha                108.099(2)
_cell_angle_beta                 92.6644(19)
_cell_angle_gamma                92.600(2)
_cell_volume                     718.99(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13294
_cell_measurement_theta_min      3.94
_cell_measurement_theta_max      68.10
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408.00
_exptl_absorpt_coefficient_mu    20.712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.072
_exptl_absorpt_correction_T_max  0.235

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            18739
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_theta_max         68.246
_diffrn_reflns_theta_min         3.975
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2616
_reflns_number_gt                2544
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.1090
_refine_ls_number_restraints     38
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         2616
_refine_ls_number_parameters     225
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0508P)²+2.9205P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.15
_refine_diff_density_min         -0.72
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.3257 6.8362
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.6763 1.2805
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.14480(8) 0.66307(8) 0.62623(5) 0.0414(2) Uani 1 1 d . . . . .
C1 C 0.3502(7) 0.7044(7) 0.5600(5) 0.0330(11) Uani 1 1 d . . . . .
C2 C 0.3463(7) 0.7490(7) 0.4556(5) 0.0331(12) Uani 1 1 d . . . . .
H2 H 0.241791 0.755347 0.414688 0.040 Uiso 1 1 calc R U . . .
C3 C 0.4989(7) 0.7842(7) 0.4118(5) 0.0323(11) Uani 1 1 d . . . . .
C4 C 0.6509(7) 0.7739(7) 0.4737(5) 0.0330(11) Uani 1 1 d . . . . .
H4 H 0.755175 0.800985 0.444961 0.040 Uiso 1 1 calc R U . . .
C5 C 0.6508(7) 0.7241(7) 0.5771(5) 0.0377(13) Uani 1 1 d . . . . .
H5 H 0.754915 0.714110 0.617081 0.045 Uiso 1 1 calc R U . . .
C6 C 0.5022(7) 0.6897(7) 0.6212(5) 0.0347(12) Uani 1 1 d . . . . .
H6 H 0.501354 0.656354 0.691907 0.042 Uiso 1 1 calc R U . . .
C7 C 0.5066(7) 0.8434(7) 0.3052(5) 0.0319(11) Uani 1 1 d . . . . .
H7 H 0.596915 0.925607 0.308454 0.038 Uiso 1 1 calc R U . . .
C8 C 0.4055(7) 0.7986(8) 0.2050(5) 0.0354(12) Uani 1 1 d D . . . .
C9 C 0.4445(7) 0.8882(7) 0.1146(5) 0.0314(11) Uani 1 1 d . . . . .
O1 O 0.5531(5) 1.0041(5) 0.1341(3) 0.0374(9) Uani 1 1 d . . . . .
O2 O 0.3530(5) 0.8254(6) 0.0110(3) 0.0402(9) Uani 1 1 d . . . . .
H2A H 0.379921 0.881139 -0.035457 0.060 Uiso 1 1 calc R U . . .
I1 I 0.01222(7) 0.90833(6) 0.23186(4) 0.03706(18) Uani 0.8168(18) 1 d . . P A 1
C10 C 0.1061(9) 0.6618(9) 0.1762(6) 0.0322(15) Uani 0.8168(18) 1 d D . P A 1
C11 C 0.2807(8) 0.6435(9) 0.1708(5) 0.0297(13) Uani 0.8168(18) 1 d . . P A 1
C12 C 0.3363(12) 0.4777(14) 0.1333(9) 0.033(2) Uani 0.8168(18) 1 d . . P A 1
H12 H 0.453845 0.462342 0.126594 0.040 Uiso 0.8168(18) 1 calc R U P A 1
C13 C 0.2228(10) 0.3326(10) 0.1053(6) 0.0351(15) Uani 0.8168(18) 1 d . . P A 1
H13 H 0.263558 0.219953 0.081533 0.042 Uiso 0.8168(18) 1 calc R U P A 1
C14 C 0.0534(9) 0.3528(9) 0.1121(6) 0.0368(15) Uani 0.8168(18) 1 d . . P A 1
H14 H -0.023064 0.253679 0.092768 0.044 Uiso 0.8168(18) 1 calc R U P A 1
C15 C -0.0085(11) 0.5159(9) 0.1466(7) 0.0331(16) Uani 0.8168(18) 1 d D . P A 1
H15 H -0.126682 0.529024 0.150363 0.040 Uiso 0.8168(18) 1 calc R U P A 1
I2 I 0.3412(5) 0.4053(4) 0.0955(3) 0.0498(10) Uani 0.1832(18) 1 d . . P A 2
C16 C 0.166(2) 0.597(3) 0.160(2) 0.042(5) Uani 0.1832(18) 1 d G U P A 2
C17 C 0.2118(15) 0.773(3) 0.196(2) 0.043(4) Uani 0.1832(18) 1 d DG U P A 2
C18 C 0.089(2) 0.892(3) 0.224(2) 0.042(4) Uani 0.1832(18) 1 d G U P A 2
H18 H 0.120308 1.012660 0.248995 0.051 Uiso 0.1832(18) 1 calc R U P A 2
C19 C -0.081(2) 0.836(3) 0.2171(18) 0.035(4) Uani 0.1832(18) 1 d G U P A 2
H19 H -0.164747 0.917933 0.236675 0.042 Uiso 0.1832(18) 1 calc R U P A 2
C20 C -0.1268(18) 0.660(3) 0.181(2) 0.042(4) Uani 0.1832(18) 1 d G U P A 2
H20 H -0.242553 0.621833 0.176196 0.050 Uiso 0.1832(18) 1 calc R U P A 2
C21 C -0.004(3) 0.541(3) 0.153(3) 0.043(5) Uani 0.1832(18) 1 d G U P A 2
H21 H -0.035305 0.420458 0.128035 0.051 Uiso 0.1832(18) 1 calc R U P A 2


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2016/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C1 1.898(6) . ?
C1 C2 1.380(8) . ?
C1 C6 1.403(8) . ?
C2 C3 1.390(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(8) . ?
C3 C7 1.476(8) . ?
C4 C5 1.393(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.361(9) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.333(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.498(8) . ?
C8 C11 1.509(8) . ?
C8 C17 1.536(13) . ?
C9 O1 1.209(7) . ?
C9 O2 1.328(6) . ?
O2 H2A 0.8400 . ?
I1 C10 2.095(7) . ?
C10 C11 1.402(9) . ?
C10 C15 1.407(9) . ?
C11 C12 1.385(13) . ?
C12 C13 1.398(13) . ?
C12 H12 0.9500 . ?
C13 C14 1.365(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(11) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
I2 C16 2.125(17) . ?
C16 C17 1.3900 . ?
C16 C21 1.3900 . ?
C17 C18 1.3900 . ?
C18 C19 1.3900 . ?
C18 H18 0.9500 . ?
C19 C20 1.3900 . ?
C19 H19 0.9500 . ?
C20 C21 1.3900 . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.3(5) . . ?
C2 C1 Br1 119.8(4) . . ?
C6 C1 Br1 117.8(4) . . ?
C1 C2 C3 118.3(5) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 119.7(5) . . ?
C2 C3 C7 122.0(5) . . ?
C4 C3 C7 118.2(5) . . ?
C5 C4 C3 120.6(5) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 120.3(5) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 118.7(5) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
C8 C7 C3 129.6(5) . . ?
C8 C7 H7 115.2 . . ?
C3 C7 H7 115.2 . . ?
C7 C8 C9 116.3(5) . . ?
C7 C8 C11 122.8(5) . . ?
C9 C8 C11 119.8(5) . . ?
C7 C8 C17 126.8(10) . . ?
C9 C8 C17 104.6(9) . . ?
O1 C9 O2 123.6(5) . . ?
O1 C9 C8 122.4(5) . . ?
O2 C9 C8 114.0(5) . . ?
C9 O2 H2A 109.5 . . ?
C11 C10 C15 120.9(7) . . ?
C11 C10 I1 120.2(5) . . ?
C15 C10 I1 118.9(6) . . ?
C12 C11 C10 118.0(7) . . ?
C12 C11 C8 120.5(6) . . ?
C10 C11 C8 121.5(6) . . ?
C11 C12 C13 121.2(8) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 120.0(7) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.9(7) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C10 119.0(8) . . ?
C14 C15 H15 120.5 . . ?
C10 C15 H15 120.5 . . ?
C17 C16 C21 120.0 . . ?
C17 C16 I2 122.5(14) . . ?
C21 C16 I2 117.1(14) . . ?
C16 C17 C18 120.0 . . ?
C16 C17 C8 109.1(16) . . ?
C18 C17 C8 130.7(16) . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.0 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C16 120.0 . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?

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
C6 C1 C2 C3 -1.6(8) . . . . ?
Br1 C1 C2 C3 177.8(4) . . . . ?
C1 C2 C3 C4 0.0(8) . . . . ?
C1 C2 C3 C7 -176.1(5) . . . . ?
C2 C3 C4 C5 1.7(8) . . . . ?
C7 C3 C4 C5 177.9(5) . . . . ?
C3 C4 C5 C6 -1.9(8) . . . . ?
C4 C5 C6 C1 0.4(8) . . . . ?
C2 C1 C6 C5 1.4(8) . . . . ?
Br1 C1 C6 C5 -178.0(4) . . . . ?
C2 C3 C7 C8 -36.4(9) . . . . ?
C4 C3 C7 C8 147.5(6) . . . . ?
C3 C7 C8 C9 177.8(5) . . . . ?
C3 C7 C8 C11 -14.0(10) . . . . ?
C3 C7 C8 C17 41.7(15) . . . . ?
C7 C8 C9 O1 -5.4(9) . . . . ?
C11 C8 C9 O1 -173.9(6) . . . . ?
C17 C8 C9 O1 139.6(11) . . . . ?
C7 C8 C9 O2 172.7(5) . . . . ?
C11 C8 C9 O2 4.1(8) . . . . ?
C17 C8 C9 O2 -42.3(12) . . . . ?
C15 C10 C11 C12 1.2(10) . . . . ?
I1 C10 C11 C12 -179.9(5) . . . . ?
C15 C10 C11 C8 -178.6(6) . . . . ?
I1 C10 C11 C8 0.3(8) . . . . ?
C7 C8 C11 C12 -71.3(9) . . . . ?
C9 C8 C11 C12 96.5(8) . . . . ?
C7 C8 C11 C10 108.5(7) . . . . ?
C9 C8 C11 C10 -83.8(7) . . . . ?
C10 C11 C12 C13 -2.0(11) . . . . ?
C8 C11 C12 C13 177.8(7) . . . . ?
C11 C12 C13 C14 1.4(12) . . . . ?
C12 C13 C14 C15 -0.1(11) . . . . ?
C13 C14 C15 C10 -0.7(11) . . . . ?
C11 C10 C15 C14 0.1(10) . . . . ?
I1 C10 C15 C14 -178.8(5) . . . . ?
C21 C16 C17 C18 0.0 . . . . ?
I2 C16 C17 C18 172.8(17) . . . . ?
C21 C16 C17 C8 175.9(16) . . . . ?
I2 C16 C17 C8 -11.3(17) . . . . ?
C7 C8 C17 C16 -101.7(14) . . . . ?
C9 C8 C17 C16 118.2(11) . . . . ?
C7 C8 C17 C18 73.6(18) . . . . ?
C9 C8 C17 C18 -66.5(16) . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C8 C17 C18 C19 -175(2) . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 C16 0.0 . . . . ?
C17 C16 C21 C20 0.0 . . . . ?
I2 C16 C21 C20 -173.2(16) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2A O1 . . 2_675 2.623(7) 0.84000 1.78000 177.3(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
