# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_w_55_2
_database_code_depnum_ccdc_archive 'CCDC 1586450'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-04-02 downloaded from the CCDC.
;
_audit_creation_date             2017-11-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            'Lithocarpin C'
_chemical_name_systematic        W-55
_chemical_formula_moiety         'C37 H42 O11'
_chemical_formula_sum            'C37 H42 O11'
_chemical_formula_weight         662.70
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.34542(7)
_cell_length_b                   14.58845(13)
_cell_length_c                   24.65138(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3360.85(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    26916
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.5520
_cell_measurement_theta_min      3.4940
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.897
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       orthorhombic
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            38401
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.602
_diffrn_reflns_theta_min         3.520
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -17.00   1.00    1.00    --  -40.98 -37.00 120.00   98
  2  ω    -33.00  65.00   1.00    1.00    --   40.98 -37.00 -90.00   98
  3  ω      1.00  82.00   1.00    1.00    --   40.98 -99.00 -60.00   81
  4  ω     94.00 178.00   1.00    1.30    --  106.95 125.00-150.00   84
  5  ω     24.00 109.00   1.00    1.30    --  106.95 -94.00-150.00   85
  6  ω     81.00 178.00   1.00    1.30    --  106.95  45.00  60.00   97
  7  ω     78.00 178.00   1.00    1.30    --  106.95  61.00 -60.00  100
  8  ω     94.00 178.00   1.00    1.30    --  106.95 125.00  60.00   84
  9  ω     78.00 178.00   1.00    1.30    --  106.95  61.00   0.00  100
 10  ω   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00 -90.00  109
 11  ω   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00  30.00  109
 12  ω     78.00 178.00   1.00    1.30    --  106.95  61.00 150.00  100
 13  ω     74.00 178.00   1.00    1.30    --  106.95  77.00  90.00  104
 14  ω     31.00 140.00   1.00    1.30    --  106.95 -77.00   0.00  109
 15  ω     79.00 178.00   1.00    1.30    --  106.95  30.00-120.00   99
 16  ω   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00  60.00  100
 17  ω      1.00  82.00   1.00    1.00    --   40.98 -99.00 120.00   81
 18  ω     78.00 178.00   1.00    1.30    --  106.95  61.00 -90.00  100
 19  ω     34.00  95.00   1.00    1.30    --  106.95-125.00-150.00   61
 20  ω     78.00 178.00   1.00    1.30    --  106.95  61.00-180.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1551832000
_diffrn_orient_matrix_UB_12      0.0184288000
_diffrn_orient_matrix_UB_13      -0.0180632000
_diffrn_orient_matrix_UB_21      0.0442860000
_diffrn_orient_matrix_UB_22      0.0135965000
_diffrn_orient_matrix_UB_23      0.0596509000
_diffrn_orient_matrix_UB_31      0.0334827000
_diffrn_orient_matrix_UB_32      -0.1031018000
_diffrn_orient_matrix_UB_33      0.0046380000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                6572
_reflns_number_total             6729
_reflns_odcompleteness_completeness 99.97
_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.
 
 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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 2792 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         6729
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.047
_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)+(0.0564P)²+0.6226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0897
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12"(H12"), C6"(H6"), C10"(H10"), C5"(H5"), C3"(H3"), C8"(H8"), C9'(H9'),
 C4"(H4")
2.b Secondary CH2 refined with riding coordinates:
 C9"(H9"A,H9"B), C7(H7A,H7B), C8'(H8'A,H8'B)
2.c Aromatic/amide H refined with riding coordinates:
 C6'(H6'), C5(H5), C4(H4), C4'(H4'), C8(H8)
2.d Idealised Me refined as rotating group:
 C12'(H12A,H12B,H12C), C11'(H11A,H11B,H11C), C7'(H7'A,H7'B,H7'C), C11"(H11D,
 H11E,H11F), C15"(H15A,H15B,H15C), C11(H11G,H11H,H11I), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.33515(15) 0.66927(10) 0.71604(5) 0.0193(3) Uani 1 1 d . . . . .
O5 O 0.28477(14) 0.46778(10) 0.71384(5) 0.0175(3) Uani 1 1 d . . . . .
O10 O -0.00964(14) 0.44279(10) 0.58264(6) 0.0201(3) Uani 1 1 d . . . . .
O2 O 0.15334(16) 0.79515(11) 0.75681(6) 0.0218(3) Uani 1 1 d . . . . .
O1" O 0.24954(16) 0.25501(10) 0.56451(5) 0.0216(3) Uani 1 1 d . . . . .
O8 O 0.07186(16) 0.45033(10) 0.48184(5) 0.0225(3) Uani 1 1 d . . . . .
O1 O -0.15600(18) 0.47548(12) 0.77254(6) 0.0281(3) Uani 1 1 d . . . . .
O6 O 0.32772(18) 0.23776(11) 0.66721(6) 0.0272(3) Uani 1 1 d . . . . .
O3 O 0.56748(17) 0.77939(12) 0.68112(6) 0.0298(4) Uani 1 1 d . . . . .
O9 O 0.05579(19) 0.60338(12) 0.48618(7) 0.0314(4) Uani 1 1 d . . . . .
O7 O 0.06598(18) 0.15610(12) 0.57071(7) 0.0331(4) Uani 1 1 d . . . . .
C1 C 0.11306(19) 0.56099(13) 0.67430(7) 0.0149(4) Uani 1 1 d . . . . .
C6 C 0.0479(2) 0.63985(13) 0.65421(7) 0.0163(4) Uani 1 1 d . . . . .
C1' C 0.38177(19) 0.56533(14) 0.64382(7) 0.0162(4) Uani 1 1 d . . . . .
C6' C 0.4680(2) 0.53990(14) 0.60014(8) 0.0177(4) Uani 1 1 d . . . . .
H6' H 0.447620 0.485755 0.581782 0.021 Uiso 1 1 calc R . . . .
C12" C 0.1464(2) 0.42661(14) 0.72223(7) 0.0174(4) Uani 1 1 d . . . . .
H12" H 0.135036 0.395477 0.757190 0.021 Uiso 1 1 calc R . . . .
C2' C 0.4171(2) 0.64504(14) 0.67221(8) 0.0177(4) Uani 1 1 d . . . . .
C7" C 0.1184(2) 0.43725(13) 0.57821(7) 0.0157(4) Uani 1 1 d . . . . .
C2 C 0.0476(2) 0.50650(14) 0.71360(7) 0.0168(4) Uani 1 1 d . . . . .
C3 C -0.0871(2) 0.52695(14) 0.73375(8) 0.0199(4) Uani 1 1 d . . . . .
C2" C 0.1643(2) 0.19695(14) 0.59035(8) 0.0192(4) Uani 1 1 d . . . . .
C3' C 0.5301(2) 0.69993(15) 0.65466(8) 0.0208(4) Uani 1 1 d . . . . .
C5 C -0.0849(2) 0.66183(14) 0.67720(8) 0.0186(4) Uani 1 1 d . . . . .
H5 H -0.129860 0.715756 0.666508 0.022 Uiso 1 1 calc R . . . .
C6" C 0.2131(2) 0.42084(13) 0.62802(7) 0.0152(4) Uani 1 1 d . . . . .
H6" H 0.300729 0.389033 0.616991 0.018 Uiso 1 1 calc R . . . .
C4 C -0.1522(2) 0.60640(15) 0.71532(8) 0.0202(4) Uani 1 1 d . . . . .
H4 H -0.241779 0.622809 0.728583 0.024 Uiso 1 1 calc R . . . .
C10" C 0.2196(2) 0.27768(14) 0.50810(7) 0.0194(4) Uani 1 1 d . . . . .
H10" H 0.115909 0.280694 0.502325 0.023 Uiso 1 1 calc R . . . .
C14" C 0.0169(2) 0.53223(15) 0.46720(8) 0.0225(4) Uani 1 1 d . . . . .
C5' C 0.5838(2) 0.59293(15) 0.58306(8) 0.0195(4) Uani 1 1 d . . . . .
C10' C 0.2744(2) 0.76578(15) 0.78906(8) 0.0202(4) Uani 1 1 d . . . . .
C5" C 0.1334(2) 0.36289(14) 0.67179(7) 0.0168(4) Uani 1 1 d . . . . .
H5" H 0.032384 0.357620 0.661642 0.020 Uiso 1 1 calc R . . . .
C4' C 0.6110(2) 0.67400(16) 0.61006(8) 0.0219(4) Uani 1 1 d . . . . .
H4' H 0.684752 0.711792 0.598158 0.026 Uiso 1 1 calc R . . . .
C9" C 0.2844(2) 0.37221(15) 0.50152(8) 0.0201(4) Uani 1 1 d . . . . .
H9"A H 0.306528 0.382154 0.463531 0.024 Uiso 1 1 calc R . . . .
H9"B H 0.373535 0.374825 0.521642 0.024 Uiso 1 1 calc R . . . .
C7 C 0.1086(2) 0.69970(15) 0.60875(8) 0.0210(4) Uani 1 1 d . . . . .
H7A H 0.212179 0.695728 0.609235 0.025 Uiso 1 1 calc R . . . .
H7B H 0.075683 0.676291 0.574096 0.025 Uiso 1 1 calc R . . . .
C3" C 0.2031(2) 0.18916(15) 0.64891(8) 0.0239(4) Uani 1 1 d . . . . .
H3" H 0.187042 0.129001 0.665512 0.029 Uiso 1 1 calc R . . . .
C8" C 0.1859(2) 0.44924(14) 0.52125(7) 0.0184(4) Uani 1 1 d . . . . .
H8" H 0.237599 0.507656 0.519846 0.022 Uiso 1 1 calc R . . . .
C9' C 0.3966(2) 0.73807(15) 0.75060(8) 0.0206(4) Uani 1 1 d . . . . .
H9' H 0.474046 0.710492 0.771884 0.025 Uiso 1 1 calc R . . . .
C13" C 0.2535(2) 0.51032(13) 0.66168(7) 0.0146(4) Uani 1 1 d . . . . .
C9 C -0.0261(3) 0.84525(16) 0.58304(9) 0.0272(5) Uani 1 1 d . . . . .
C12' C 0.2295(3) 0.68372(16) 0.82309(9) 0.0263(4) Uani 1 1 d . . . . .
H12A H 0.148941 0.700134 0.845203 0.039 Uiso 1 1 calc GR . . . .
H12B H 0.307643 0.665344 0.845911 0.039 Uiso 1 1 calc GR . . . .
H12C H 0.203625 0.633891 0.799622 0.039 Uiso 1 1 calc GR . . . .
C4" C 0.1905(2) 0.26864(15) 0.68565(8) 0.0230(4) Uani 1 1 d . . . . .
H4" H 0.170516 0.250837 0.723223 0.028 Uiso 1 1 calc R . . . .
C11' C 0.3171(2) 0.84705(16) 0.82430(9) 0.0258(4) Uani 1 1 d . . . . .
H11A H 0.336274 0.899147 0.801643 0.039 Uiso 1 1 calc GR . . . .
H11B H 0.401486 0.831866 0.844627 0.039 Uiso 1 1 calc GR . . . .
H11C H 0.240566 0.861365 0.848842 0.039 Uiso 1 1 calc GR . . . .
C7' C 0.6776(2) 0.56262(17) 0.53663(9) 0.0251(4) Uani 1 1 d . . . . .
H7'A H 0.767308 0.540792 0.550568 0.038 Uiso 1 1 calc GR . . . .
H7'B H 0.694396 0.613491 0.512764 0.038 Uiso 1 1 calc GR . . . .
H7'C H 0.630955 0.514272 0.517015 0.038 Uiso 1 1 calc GR . . . .
C8 C 0.0651(3) 0.79831(16) 0.61395(9) 0.0266(5) Uani 1 1 d . . . . .
H8 H 0.106925 0.830719 0.642292 0.032 Uiso 1 1 calc R . . . .
C8' C 0.4574(2) 0.81460(16) 0.71617(9) 0.0269(5) Uani 1 1 d . . . . .
H8'A H 0.381832 0.841778 0.694533 0.032 Uiso 1 1 calc R . . . .
H8'B H 0.496997 0.861888 0.739414 0.032 Uiso 1 1 calc R . . . .
C11" C 0.2837(3) 0.20521(16) 0.47200(9) 0.0294(5) Uani 1 1 d . . . . .
H11D H 0.384056 0.199568 0.479617 0.044 Uiso 1 1 calc GR . . . .
H11E H 0.270683 0.222260 0.434711 0.044 Uiso 1 1 calc GR . . . .
H11F H 0.237248 0.147602 0.478660 0.044 Uiso 1 1 calc GR . . . .
C15" C -0.0948(3) 0.52088(19) 0.42394(9) 0.0331(5) Uani 1 1 d . . . . .
H15A H -0.050954 0.497411 0.391568 0.050 Uiso 1 1 calc GR . . . .
H15B H -0.137983 0.579178 0.416350 0.050 Uiso 1 1 calc GR . . . .
H15C H -0.166734 0.478789 0.436247 0.050 Uiso 1 1 calc GR . . . .
C11 C -0.1018(2) 0.80671(18) 0.53414(10) 0.0328(5) Uani 1 1 d . . . . .
H11G H -0.070065 0.838207 0.502137 0.049 Uiso 1 1 calc GR . . . .
H11H H -0.203211 0.814800 0.538254 0.049 Uiso 1 1 calc GR . . . .
H11I H -0.080545 0.742572 0.530864 0.049 Uiso 1 1 calc GR . . . .
C10 C -0.0624(4) 0.94295(19) 0.59585(12) 0.0464(7) Uani 1 1 d . . . . .
H10A H -0.161663 0.947238 0.605532 0.070 Uiso 1 1 calc GR . . . .
H10B H -0.044193 0.980487 0.564620 0.070 Uiso 1 1 calc GR . . . .
H10C H -0.004583 0.963694 0.625611 0.070 Uiso 1 1 calc GR . . . .
H1 H -0.146(3) 0.417(2) 0.7665(12) 0.035(8) Uiso 1 1 d . . . . .
H2 H 0.132(4) 0.751(3) 0.7370(14) 0.046(9) Uiso 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
O4 C2' 1.371(2) . ?
O4 C9' 1.436(2) . ?
O5 C12" 1.440(2) . ?
O5 C13" 1.457(2) . ?
O10 C7" 1.204(2) . ?
O2 C10' 1.448(2) . ?
O2 H2 0.83(4) . ?
O1" C2" 1.326(2) . ?
O1" C10" 1.457(2) . ?
O8 C14" 1.350(3) . ?
O8 C8" 1.442(2) . ?
O1 C3 1.376(2) . ?
O1 H1 0.87(3) . ?
O6 C3" 1.436(3) . ?
O6 C4" 1.433(3) . ?
O3 C3' 1.375(3) . ?
O3 C8' 1.438(3) . ?
O9 C14" 1.195(3) . ?
O7 C2" 1.198(3) . ?
C1 C6 1.393(3) . ?
C1 C2 1.395(3) . ?
C1 C13" 1.538(3) . ?
C6 C5 1.402(3) . ?
C6 C7 1.529(3) . ?
C1' C6' 1.395(3) . ?
C1' C2' 1.397(3) . ?
C1' C13" 1.508(3) . ?
C6' H6' 0.9300 . ?
C6' C5' 1.395(3) . ?
C12" H12" 0.9800 . ?
C12" C2 1.502(3) . ?
C12" C5" 1.557(3) . ?
C2' C3' 1.394(3) . ?
C7" C6" 1.532(3) . ?
C7" C8" 1.549(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.386(3) . ?
C2" C3" 1.493(3) . ?
C3' C4' 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.390(3) . ?
C6" H6" 0.9800 . ?
C6" C5" 1.560(3) . ?
C6" C13" 1.592(3) . ?
C4 H4 0.9300 . ?
C10" H10" 0.9800 . ?
C10" C9" 1.515(3) . ?
C10" C11" 1.506(3) . ?
C14" C15" 1.501(3) . ?
C5' C4' 1.381(3) . ?
C5' C7' 1.508(3) . ?
C10' C9' 1.539(3) . ?
C10' C12' 1.521(3) . ?
C10' C11' 1.523(3) . ?
C5" H5" 0.9800 . ?
C5" C4" 1.514(3) . ?
C4' H4' 0.9300 . ?
C9" H9"A 0.9700 . ?
C9" H9"B 0.9700 . ?
C9" C8" 1.532(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.501(3) . ?
C3" H3" 0.9800 . ?
C3" C4" 1.476(3) . ?
C8" H8" 0.9800 . ?
C9' H9' 0.9800 . ?
C9' C8' 1.513(3) . ?
C9 C8 1.332(3) . ?
C9 C11 1.507(3) . ?
C9 C10 1.499(4) . ?
C12' H12A 0.9600 . ?
C12' H12B 0.9600 . ?
C12' H12C 0.9600 . ?
C4" H4" 0.9800 . ?
C11' H11A 0.9600 . ?
C11' H11B 0.9600 . ?
C11' H11C 0.9600 . ?
C7' H7'A 0.9600 . ?
C7' H7'B 0.9600 . ?
C7' H7'C 0.9600 . ?
C8 H8 0.9300 . ?
C8' H8'A 0.9700 . ?
C8' H8'B 0.9700 . ?
C11" H11D 0.9600 . ?
C11" H11E 0.9600 . ?
C11" H11F 0.9600 . ?
C15" H15A 0.9600 . ?
C15" H15B 0.9600 . ?
C15" H15C 0.9600 . ?
C11 H11G 0.9600 . ?
C11 H11H 0.9600 . ?
C11 H11I 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2' O4 C9' 115.08(15) . . ?
C12" O5 C13" 97.14(13) . . ?
C10' O2 H2 106(2) . . ?
C2" O1" C10" 119.23(16) . . ?
C14" O8 C8" 118.10(16) . . ?
C3 O1 H1 112(2) . . ?
C4" O6 C3" 61.92(14) . . ?
C3' O3 C8' 113.85(16) . . ?
C6 C1 C2 121.75(18) . . ?
C6 C1 C13" 134.27(17) . . ?
C2 C1 C13" 103.94(16) . . ?
C1 C6 C5 115.61(18) . . ?
C1 C6 C7 124.76(17) . . ?
C5 C6 C7 119.60(18) . . ?
C6' C1' C2' 118.12(18) . . ?
C6' C1' C13" 122.88(18) . . ?
C2' C1' C13" 118.99(17) . . ?
C1' C6' H6' 118.9 . . ?
C5' C6' C1' 122.23(19) . . ?
C5' C6' H6' 118.9 . . ?
O5 C12" H12" 114.7 . . ?
O5 C12" C2 102.01(15) . . ?
O5 C12" C5" 101.79(14) . . ?
C2 C12" H12" 114.7 . . ?
C2 C12" C5" 107.58(15) . . ?
C5" C12" H12" 114.7 . . ?
O4 C2' C1' 118.50(17) . . ?
O4 C2' C3' 121.33(18) . . ?
C3' C2' C1' 120.12(17) . . ?
O10 C7" C6" 120.76(17) . . ?
O10 C7" C8" 118.64(17) . . ?
C6" C7" C8" 120.59(16) . . ?
C1 C2 C12" 105.71(16) . . ?
C3 C2 C1 121.67(19) . . ?
C3 C2 C12" 132.44(19) . . ?
O1 C3 C2 123.8(2) . . ?
O1 C3 C4 118.63(18) . . ?
C4 C3 C2 117.46(19) . . ?
O1" C2" C3" 111.57(18) . . ?
O7 C2" O1" 125.78(19) . . ?
O7 C2" C3" 122.64(19) . . ?
O3 C3' C2' 121.97(18) . . ?
O3 C3' C4' 117.85(18) . . ?
C4' C3' C2' 120.16(19) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 C6 122.75(19) . . ?
C4 C5 H5 118.6 . . ?
C7" C6" H6" 109.5 . . ?
C7" C6" C5" 111.33(15) . . ?
C7" C6" C13" 115.25(15) . . ?
C5" C6" H6" 109.5 . . ?
C5" C6" C13" 101.37(14) . . ?
C13" C6" H6" 109.5 . . ?
C3 C4 C5 120.64(18) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
O1" C10" H10" 109.8 . . ?
O1" C10" C9" 103.40(15) . . ?
O1" C10" C11" 109.15(17) . . ?
C9" C10" H10" 109.8 . . ?
C11" C10" H10" 109.8 . . ?
C11" C10" C9" 114.61(17) . . ?
O8 C14" C15" 110.90(19) . . ?
O9 C14" O8 123.28(19) . . ?
O9 C14" C15" 125.8(2) . . ?
C6' C5' C7' 121.16(19) . . ?
C4' C5' C6' 118.20(18) . . ?
C4' C5' C7' 120.64(19) . . ?
O2 C10' C9' 108.63(16) . . ?
O2 C10' C12' 108.68(17) . . ?
O2 C10' C11' 106.72(17) . . ?
C12' C10' C9' 109.75(18) . . ?
C12' C10' C11' 111.75(17) . . ?
C11' C10' C9' 111.18(17) . . ?
C12" C5" C6" 101.05(15) . . ?
C12" C5" H5" 109.0 . . ?
C6" C5" H5" 109.0 . . ?
C4" C5" C12" 109.54(16) . . ?
C4" C5" C6" 118.71(16) . . ?
C4" C5" H5" 109.0 . . ?
C3' C4' H4' 119.5 . . ?
C5' C4' C3' 121.00(19) . . ?
C5' C4' H4' 119.5 . . ?
C10" C9" H9"A 108.9 . . ?
C10" C9" H9"B 108.9 . . ?
C10" C9" C8" 113.17(16) . . ?
H9"A C9" H9"B 107.8 . . ?
C8" C9" H9"A 108.9 . . ?
C8" C9" H9"B 108.9 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 112.60(17) . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
O6 C3" C2" 117.59(18) . . ?
O6 C3" H3" 115.8 . . ?
O6 C3" C4" 58.94(14) . . ?
C2" C3" H3" 115.8 . . ?
C4" C3" C2" 120.95(18) . . ?
C4" C3" H3" 115.8 . . ?
O8 C8" C7" 108.09(15) . . ?
O8 C8" C9" 103.79(15) . . ?
O8 C8" H8" 109.3 . . ?
C7" C8" H8" 109.3 . . ?
C9" C8" C7" 116.71(16) . . ?
C9" C8" H8" 109.3 . . ?
O4 C9' C10' 104.60(15) . . ?
O4 C9' H9' 109.0 . . ?
O4 C9' C8' 109.46(16) . . ?
C10' C9' H9' 109.0 . . ?
C8' C9' C10' 115.50(18) . . ?
C8' C9' H9' 109.0 . . ?
O5 C13" C1 101.38(14) . . ?
O5 C13" C1' 108.96(14) . . ?
O5 C13" C6" 99.11(14) . . ?
C1 C13" C6" 107.26(15) . . ?
C1' C13" C1 118.78(16) . . ?
C1' C13" C6" 118.21(15) . . ?
C8 C9 C11 124.5(2) . . ?
C8 C9 C10 120.9(2) . . ?
C10 C9 C11 114.6(2) . . ?
C10' C12' H12A 109.5 . . ?
C10' C12' H12B 109.5 . . ?
C10' C12' H12C 109.5 . . ?
H12A C12' H12B 109.5 . . ?
H12A C12' H12C 109.5 . . ?
H12B C12' H12C 109.5 . . ?
O6 C4" C5" 121.95(18) . . ?
O6 C4" C3" 59.14(13) . . ?
O6 C4" H4" 112.8 . . ?
C5" C4" H4" 112.8 . . ?
C3" C4" C5" 127.09(18) . . ?
C3" C4" H4" 112.8 . . ?
C10' C11' H11A 109.5 . . ?
C10' C11' H11B 109.5 . . ?
C10' C11' H11C 109.5 . . ?
H11A C11' H11B 109.5 . . ?
H11A C11' H11C 109.5 . . ?
H11B C11' H11C 109.5 . . ?
C5' C7' H7'A 109.5 . . ?
C5' C7' H7'B 109.5 . . ?
C5' C7' H7'C 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
C7 C8 H8 115.9 . . ?
C9 C8 C7 128.1(2) . . ?
C9 C8 H8 115.9 . . ?
O3 C8' C9' 110.00(19) . . ?
O3 C8' H8'A 109.7 . . ?
O3 C8' H8'B 109.7 . . ?
C9' C8' H8'A 109.7 . . ?
C9' C8' H8'B 109.7 . . ?
H8'A C8' H8'B 108.2 . . ?
C10" C11" H11D 109.5 . . ?
C10" C11" H11E 109.5 . . ?
C10" C11" H11F 109.5 . . ?
H11D C11" H11E 109.5 . . ?
H11D C11" H11F 109.5 . . ?
H11E C11" H11F 109.5 . . ?
C14" C15" H15A 109.5 . . ?
C14" C15" H15B 109.5 . . ?
C14" C15" H15C 109.5 . . ?
H15A C15" H15B 109.5 . . ?
H15A C15" H15C 109.5 . . ?
H15B C15" H15C 109.5 . . ?
C9 C11 H11G 109.5 . . ?
C9 C11 H11H 109.5 . . ?
C9 C11 H11I 109.5 . . ?
H11G C11 H11H 109.5 . . ?
H11G C11 H11I 109.5 . . ?
H11H C11 H11I 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C2' C3' O3 1.9(3) . . . . ?
O4 C2' C3' C4' -179.75(18) . . . . ?
O4 C9' C8' O3 -60.7(2) . . . . ?
O5 C12" C2 C1 33.24(18) . . . . ?
O5 C12" C2 C3 -151.9(2) . . . . ?
O5 C12" C5" C6" -34.41(17) . . . . ?
O5 C12" C5" C4" 91.65(18) . . . . ?
O10 C7" C6" C5" 31.0(3) . . . . ?
O10 C7" C6" C13" -83.8(2) . . . . ?
O10 C7" C8" O8 -9.4(3) . . . . ?
O10 C7" C8" C9" -125.9(2) . . . . ?
O2 C10' C9' O4 -56.1(2) . . . . ?
O2 C10' C9' C8' 64.3(2) . . . . ?
O1" C2" C3" O6 -4.5(3) . . . . ?
O1" C2" C3" C4" 64.1(3) . . . . ?
O1" C10" C9" C8" -82.80(19) . . . . ?
O1 C3 C4 C5 178.31(18) . . . . ?
O6 C3" C4" C5" 108.7(2) . . . . ?
O3 C3' C4' C5' 176.99(19) . . . . ?
O7 C2" C3" O6 176.86(19) . . . . ?
O7 C2" C3" C4" -114.6(3) . . . . ?
C1 C6 C5 C4 -3.6(3) . . . . ?
C1 C6 C7 C8 -150.64(19) . . . . ?
C1 C2 C3 O1 -179.89(18) . . . . ?
C1 C2 C3 C4 -3.1(3) . . . . ?
C6 C1 C2 C12" 177.07(16) . . . . ?
C6 C1 C2 C3 1.5(3) . . . . ?
C6 C1 C13" O5 151.3(2) . . . . ?
C6 C1 C13" C1' 32.0(3) . . . . ?
C6 C1 C13" C6" -105.3(2) . . . . ?
C6 C5 C4 C3 2.1(3) . . . . ?
C6 C7 C8 C9 -109.2(3) . . . . ?
C1' C6' C5' C4' -1.2(3) . . . . ?
C1' C6' C5' C7' 178.39(18) . . . . ?
C1' C2' C3' O3 179.35(18) . . . . ?
C1' C2' C3' C4' -2.3(3) . . . . ?
C6' C1' C2' O4 -178.35(17) . . . . ?
C6' C1' C2' C3' 4.1(3) . . . . ?
C6' C1' C13" O5 110.30(19) . . . . ?
C6' C1' C13" C1 -134.44(19) . . . . ?
C6' C1' C13" C6" -1.7(3) . . . . ?
C6' C5' C4' C3' 3.2(3) . . . . ?
C12" O5 C13" C1 50.48(15) . . . . ?
C12" O5 C13" C1' 176.52(15) . . . . ?
C12" O5 C13" C6" -59.33(15) . . . . ?
C12" C2 C3 O1 5.9(3) . . . . ?
C12" C2 C3 C4 -177.28(19) . . . . ?
C12" C5" C4" O6 -104.0(2) . . . . ?
C12" C5" C4" C3" -177.4(2) . . . . ?
C2' O4 C9' C10' 169.41(16) . . . . ?
C2' O4 C9' C8' 45.1(2) . . . . ?
C2' C1' C6' C5' -2.4(3) . . . . ?
C2' C1' C13" O5 -69.3(2) . . . . ?
C2' C1' C13" C1 46.0(2) . . . . ?
C2' C1' C13" C6" 178.73(16) . . . . ?
C2' C3' C4' C5' -1.5(3) . . . . ?
C7" C6" C5" C12" -124.82(16) . . . . ?
C7" C6" C5" C4" 115.49(19) . . . . ?
C7" C6" C13" O5 156.97(15) . . . . ?
C7" C6" C13" C1 52.0(2) . . . . ?
C7" C6" C13" C1' -85.7(2) . . . . ?
C2 C1 C6 C5 1.8(3) . . . . ?
C2 C1 C6 C7 -176.05(18) . . . . ?
C2 C1 C13" O5 -31.04(17) . . . . ?
C2 C1 C13" C1' -150.29(16) . . . . ?
C2 C1 C13" C6" 72.36(17) . . . . ?
C2 C12" C5" C6" 72.40(18) . . . . ?
C2 C12" C5" C4" -161.54(17) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C2" O1" C10" C9" 153.56(17) . . . . ?
C2" O1" C10" C11" -84.0(2) . . . . ?
C2" C3" C4" O6 -105.6(2) . . . . ?
C2" C3" C4" C5" 3.1(4) . . . . ?
C3' O3 C8' C9' 46.7(2) . . . . ?
C5 C6 C7 C8 31.6(3) . . . . ?
C6" C7" C8" O8 171.90(16) . . . . ?
C6" C7" C8" C9" 55.5(2) . . . . ?
C6" C5" C4" O6 11.2(3) . . . . ?
C6" C5" C4" C3" -62.2(3) . . . . ?
C10" O1" C2" O7 4.2(3) . . . . ?
C10" O1" C2" C3" -174.45(16) . . . . ?
C10" C9" C8" O8 -69.86(19) . . . . ?
C10" C9" C8" C7" 48.9(2) . . . . ?
C14" O8 C8" C7" 92.8(2) . . . . ?
C14" O8 C8" C9" -142.63(17) . . . . ?
C10' C9' C8' O3 -178.38(17) . . . . ?
C5" C12" C2 C1 -73.41(19) . . . . ?
C5" C12" C2 C3 101.5(2) . . . . ?
C5" C6" C13" O5 36.64(16) . . . . ?
C5" C6" C13" C1 -68.37(17) . . . . ?
C5" C6" C13" C1' 153.99(16) . . . . ?
C7 C6 C5 C4 174.39(18) . . . . ?
C3" O6 C4" C5" -117.1(2) . . . . ?
C8" O8 C14" O9 -1.8(3) . . . . ?
C8" O8 C14" C15" 177.02(17) . . . . ?
C8" C7" C6" C5" -150.42(17) . . . . ?
C8" C7" C6" C13" 94.9(2) . . . . ?
C9' O4 C2' C1' 165.67(17) . . . . ?
C9' O4 C2' C3' -16.8(3) . . . . ?
C13" O5 C12" C2 -51.48(16) . . . . ?
C13" O5 C12" C5" 59.61(15) . . . . ?
C13" C1 C6 C5 179.16(19) . . . . ?
C13" C1 C6 C7 1.3(3) . . . . ?
C13" C1 C2 C12" -0.99(19) . . . . ?
C13" C1 C2 C3 -176.56(17) . . . . ?
C13" C1' C6' C5' 178.03(18) . . . . ?
C13" C1' C2' O4 1.3(3) . . . . ?
C13" C1' C2' C3' -176.30(18) . . . . ?
C13" C6" C5" C12" -1.75(17) . . . . ?
C13" C6" C5" C4" -121.45(18) . . . . ?
C12' C10' C9' O4 62.6(2) . . . . ?
C12' C10' C9' C8' -176.98(18) . . . . ?
C4" O6 C3" C2" 111.3(2) . . . . ?
C11' C10' C9' O4 -173.20(17) . . . . ?
C11' C10' C9' C8' -52.8(2) . . . . ?
C7' C5' C4' C3' -176.4(2) . . . . ?
C8' O3 C3' C2' -18.2(3) . . . . ?
C8' O3 C3' C4' 163.3(2) . . . . ?
C11" C10" C9" C8" 158.50(18) . . . . ?
C11 C9 C8 C7 -2.0(4) . . . . ?
C10 C9 C8 C7 177.1(2) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.028 -0.020 0.200 32.5 3.5 ?
2 0.028 0.480 0.300 32.5 3.5 ?
3 0.472 0.520 0.800 32.5 3.5 ?
4 0.528 0.020 0.700 32.5 3.5 ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.042
_oxdiff_exptl_absorpt_empirical_full_min 0.656
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 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_w-36
_database_code_depnum_ccdc_archive 'CCDC 1586451'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-04-02 downloaded from the CCDC.
;
_audit_creation_date             2017-11-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            'Lithocarpin A'
_chemical_name_systematic        w-36
_chemical_formula_moiety         'C H Cl3, C37 H42 O11'
_chemical_formula_sum            'C38 H43 Cl3 O11'
_chemical_formula_weight         782.07
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   12.0999(3)
_cell_length_b                   8.9388(2)
_cell_length_c                   17.0397(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.378(2)
_cell_angle_gamma                90
_cell_volume                     1842.95(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8832
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3420
_cell_measurement_theta_min      4.4480
_shelx_estimated_absorpt_T_max   0.750
_shelx_estimated_absorpt_T_min   0.682
_exptl_absorpt_coefficient_mu    2.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17295
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.760
_diffrn_reflns_theta_min         3.653
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00  39.00   1.00    1.00    --  -40.98  19.00  30.00  121
  2  ω     23.00  97.00   1.00    1.00    --   40.98-125.00 -60.00   74
  3  ω     17.00 115.00   1.00    1.00    --   40.98  37.00-150.00   98
  4  ω     79.00 178.00   1.00    4.51    --  107.58  30.00 -30.00   99
  5  ω     79.00 178.00   1.00    4.51    --  107.58  30.00 120.00   99
  6  ω     94.00 178.00   1.00    4.51    --  107.58 125.00 -90.00   84
  7  ω     97.00 178.00   1.00    4.51    --  107.58 119.00 140.00   81
  8  ω     34.00 122.00   1.00    4.51    --  107.58-125.00  90.00   88
  9  ω     35.00 137.00   1.00    4.51    --  107.58 -61.00  30.00  102
 10  ω   -115.00 -17.00   1.00    1.00    --  -40.98 -37.00   0.00   98
 11  ω    -31.00  69.00   1.00    1.00    --   40.98 -57.00  60.00  100
 12  ω     17.00 115.00   1.00    1.00    --   40.98  37.00 -60.00   98
 13  ω     31.00 140.00   1.00    4.51    --  107.58 -77.00-180.00  109
 14  ω     79.00 178.00   1.00    4.51    --  107.58  30.00-120.00   99
 15  ω     75.00 178.00   1.00    4.51    --  107.58  77.00 150.00  103
 16  ω     78.00 152.00   1.00    4.51    --  107.58  61.00   0.00   74
 17  ω     75.00 178.00   1.00    4.51    --  107.58  77.00  30.00  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1157509000
_diffrn_orient_matrix_UB_12      -0.0677329000
_diffrn_orient_matrix_UB_13      0.0130446000
_diffrn_orient_matrix_UB_21      0.0230470000
_diffrn_orient_matrix_UB_22      0.0126440000
_diffrn_orient_matrix_UB_23      -0.0885270000
_diffrn_orient_matrix_UB_31      0.0479837000
_diffrn_orient_matrix_UB_32      0.1579173000
_diffrn_orient_matrix_UB_33      0.0127077000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.836
_reflns_Friedel_fraction_max     0.803
_reflns_number_gt                6398
_reflns_number_total             6703
_reflns_odcompleteness_completeness 99.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.202
_refine_diff_density_min         -1.438
_refine_diff_density_rms         0.149
_refine_ls_abs_structure_details 
;
 Flack x determined using 2414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.087(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         6703
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0906
_refine_ls_restrained_S_all      1.036
_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)+(0.1996P)²+2.7116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2611
_refine_ls_wR_factor_ref         0.2650
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8"(H8"), C5"(H5"), C13"(H13"), C9'(H9'), C6"(H6"), C4"(H4"), C3"(H3"),
 C10"(H10"), C1S(H1S)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9"(H9"A,H9"B), C8'(H8'A,H8'B)
2.c Aromatic/amide H refined with riding coordinates:
 C6'(H6'), C4(H4A), C5(H5), C4'(H4'), C8(H8)
2.d Idealised Me refined as rotating group:
 C7'(H7'A,H7'B,H7'C), C12'(H12A,H12B,H12C), C15"(H15A,H15B,H15C), C11'(H11A,
 H11B,H11C), C11"(H11D,H11E,H11F), C11(H11G,H11H,H11I), C10(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_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
Cl3 Cl 0.2117(3) 0.0886(4) 0.85650(19) 0.0737(9) Uani 1 1 d . . . . .
O5 O 0.4565(3) 0.4972(5) 0.6743(2) 0.0150(8) Uani 1 1 d . . . . .
O2 O 0.3296(4) 0.5700(5) 0.5385(2) 0.0203(9) Uani 1 1 d . . . . .
Cl2 Cl 0.0289(3) 0.2815(5) 0.8894(3) 0.0982(14) Uani 1 1 d . . . A 1
O10 O 0.5210(4) 0.2848(5) 0.8104(3) 0.0203(9) Uani 1 1 d . . . . .
Cl1 Cl 0.0541(3) -0.0011(7) 0.9749(3) 0.0981(14) Uani 1 1 d . . . B 1
O1 O 0.5835(4) 0.9375(6) 0.7248(3) 0.0225(9) Uani 1 1 d . . . . .
H1 H 0.590562 1.026279 0.713865 0.034 Uiso 1 1 calc GR . . . .
O1" O 0.4302(4) 0.5096(6) 0.9679(3) 0.0257(10) Uani 1 1 d . . . . .
O6 O 0.2874(4) 0.6854(5) 0.8888(3) 0.0227(9) Uani 1 1 d . . . . .
O8 O 0.7026(4) 0.2925(6) 0.8919(2) 0.0224(9) Uani 1 1 d . . . . .
O4 O 0.4065(4) 0.7124(6) 0.3496(3) 0.0248(10) Uani 1 1 d . . . . .
H4 H 0.461492 0.759960 0.336789 0.037 Uiso 1 1 calc GR . . . .
O3 O 0.1722(4) 0.4193(6) 0.4429(3) 0.0293(11) Uani 1 1 d . . . . .
O9 O 0.7724(4) 0.3217(7) 0.7711(3) 0.0311(11) Uani 1 1 d . . . . .
O7 O 0.2995(5) 0.3458(6) 1.0047(3) 0.0329(12) Uani 1 1 d . . . . .
C1 C 0.3392(5) 0.6991(7) 0.6921(3) 0.0163(11) Uani 1 1 d . . . . .
C2 C 0.4494(5) 0.7458(7) 0.7088(3) 0.0169(11) Uani 1 1 d . . . . .
C6 C 0.2550(5) 0.8026(8) 0.6779(3) 0.0201(12) Uani 1 1 d . . . . .
C1' C 0.2622(5) 0.4433(7) 0.6505(3) 0.0164(11) Uani 1 1 d . . . . .
C3 C 0.4772(5) 0.8941(7) 0.7104(3) 0.0177(12) Uani 1 1 d . . . . .
C5' C 0.1060(5) 0.2707(8) 0.6372(4) 0.0229(13) Uani 1 1 d . . . . .
C7" C 0.5438(5) 0.4095(7) 0.8323(3) 0.0170(12) Uani 1 1 d . . . . .
C2" C 0.3284(6) 0.4574(8) 0.9697(4) 0.0246(14) Uani 1 1 d . . . . .
C6' C 0.1855(5) 0.3441(7) 0.6835(4) 0.0200(12) Uani 1 1 d . . . . .
H6' H 0.187481 0.326578 0.737259 0.024 Uiso 1 1 calc R . . . .
C2' C 0.2578(5) 0.4678(7) 0.5694(4) 0.0203(12) Uani 1 1 d . . . . .
C8" C 0.6474(5) 0.4328(8) 0.8839(4) 0.0207(12) Uani 1 1 d . . . . .
H8" H 0.696709 0.504419 0.858269 0.025 Uiso 1 1 calc R . . . .
C3' C 0.1782(5) 0.3940(8) 0.5227(4) 0.0220(13) Uani 1 1 d . . . . .
C5" C 0.3535(5) 0.4945(7) 0.7887(3) 0.0179(11) Uani 1 1 d . . . . .
H5" H 0.348763 0.385827 0.795279 0.021 Uiso 1 1 calc R . . . .
C14" C 0.7589(5) 0.2445(9) 0.8273(4) 0.0248(13) Uani 1 1 d . . . . .
C13" C 0.5122(5) 0.6024(7) 0.7246(3) 0.0143(11) Uani 1 1 d . . . . .
H13" H 0.592381 0.608839 0.717441 0.017 Uiso 1 1 calc R . . . .
C12" C 0.3433(4) 0.5302(7) 0.6987(3) 0.0155(11) Uani 1 1 d . . . . .
C9' C 0.3340(5) 0.5760(8) 0.4539(3) 0.0184(12) Uani 1 1 d . . . . .
H9' H 0.379203 0.492622 0.435030 0.022 Uiso 1 1 calc R . . . .
C4 C 0.3925(5) 0.9994(7) 0.6974(4) 0.0215(12) Uani 1 1 d . . . . .
H4A H 0.408521 1.100967 0.700298 0.026 Uiso 1 1 calc R . . . .
C6" C 0.4746(5) 0.5431(7) 0.8071(3) 0.0159(11) Uani 1 1 d . . . . .
H6" H 0.476900 0.622692 0.846689 0.019 Uiso 1 1 calc R . . . .
C4" C 0.2620(5) 0.5654(8) 0.8363(4) 0.0200(12) Uani 1 1 d . . . . .
H4" H 0.191990 0.577369 0.807667 0.024 Uiso 1 1 calc R . . . .
C10' C 0.3918(5) 0.7230(8) 0.4341(3) 0.0210(13) Uani 1 1 d . . . . .
C3" C 0.2497(5) 0.5492(8) 0.9222(4) 0.0233(13) Uani 1 1 d . . . . .
H3" H 0.173472 0.550646 0.941274 0.028 Uiso 1 1 calc R . . . .
C5 C 0.2852(6) 0.9534(8) 0.6803(4) 0.0240(13) Uani 1 1 d . . . . .
H5 H 0.231691 1.025555 0.670036 0.029 Uiso 1 1 calc R . . . .
C10" C 0.5198(6) 0.4243(8) 1.0062(4) 0.0255(14) Uani 1 1 d . . . . .
H10" H 0.512242 0.317515 0.994174 0.031 Uiso 1 1 calc R . . . .
C7 C 0.1358(5) 0.7653(9) 0.6593(4) 0.0270(14) Uani 1 1 d . . . . .
H7A H 0.107663 0.837686 0.621723 0.032 Uiso 1 1 calc R . . . .
H7B H 0.132816 0.667563 0.634652 0.032 Uiso 1 1 calc R . . . .
C4' C 0.1041(5) 0.2956(8) 0.5573(4) 0.0249(13) Uani 1 1 d . . . . .
H4' H 0.052541 0.245797 0.526146 0.030 Uiso 1 1 calc R . . . .
C9" C 0.6228(6) 0.4869(9) 0.9678(4) 0.0276(14) Uani 1 1 d . . . . .
H9"A H 0.685866 0.462336 1.000775 0.033 Uiso 1 1 calc R . . . .
H9"B H 0.616554 0.595075 0.966698 0.033 Uiso 1 1 calc R . . . .
C8' C 0.2189(6) 0.5608(9) 0.4206(4) 0.0268(14) Uani 1 1 d . . . . .
H8'A H 0.172819 0.641328 0.440050 0.032 Uiso 1 1 calc R . . . .
H8'B H 0.221222 0.567997 0.363863 0.032 Uiso 1 1 calc R . . . .
C7' C 0.0219(5) 0.1709(8) 0.6749(4) 0.0268(14) Uani 1 1 d . . . . .
H7'A H 0.052214 0.129545 0.722371 0.040 Uiso 1 1 calc GR . . . .
H7'B H 0.002843 0.091274 0.639483 0.040 Uiso 1 1 calc GR . . . .
H7'C H -0.043006 0.227924 0.686867 0.040 Uiso 1 1 calc GR . . . .
C8 C 0.0618(6) 0.7647(9) 0.7299(5) 0.0301(15) Uani 1 1 d . . . . .
H8 H 0.085905 0.817104 0.773946 0.036 Uiso 1 1 calc R . . . .
C12' C 0.5046(6) 0.7290(9) 0.4743(4) 0.0301(15) Uani 1 1 d . . . . .
H12A H 0.545993 0.641016 0.461163 0.045 Uiso 1 1 calc GR . . . .
H12B H 0.494987 0.733621 0.530152 0.045 Uiso 1 1 calc GR . . . .
H12C H 0.543799 0.816189 0.456987 0.045 Uiso 1 1 calc GR . . . .
C15" C 0.7949(6) 0.0864(9) 0.8368(4) 0.0321(16) Uani 1 1 d . . . . .
H15A H 0.832257 0.074996 0.886377 0.048 Uiso 1 1 calc GR . . . .
H15B H 0.844334 0.060371 0.795154 0.048 Uiso 1 1 calc GR . . . .
H15C H 0.731547 0.021918 0.835162 0.048 Uiso 1 1 calc GR . . . .
C9 C -0.0367(6) 0.6943(9) 0.7346(6) 0.0372(18) Uani 1 1 d . . . . .
C11' C 0.3255(8) 0.8593(10) 0.4523(4) 0.0358(17) Uani 1 1 d . . . . .
H11A H 0.369736 0.946886 0.443985 0.054 Uiso 1 1 calc GR . . . .
H11B H 0.302282 0.855907 0.506056 0.054 Uiso 1 1 calc GR . . . .
H11C H 0.261636 0.862659 0.418581 0.054 Uiso 1 1 calc GR . . . .
C11" C 0.5161(8) 0.4489(10) 1.0941(4) 0.039(2) Uani 1 1 d . . . . .
H11D H 0.521039 0.553985 1.105095 0.059 Uiso 1 1 calc GR . . . .
H11E H 0.577125 0.397901 1.118544 0.059 Uiso 1 1 calc GR . . . .
H11F H 0.447987 0.410290 1.114298 0.059 Uiso 1 1 calc GR . . . .
C11 C -0.0864(7) 0.6070(11) 0.6695(7) 0.048(2) Uani 1 1 d . . . . .
H11G H -0.147626 0.661330 0.647529 0.073 Uiso 1 1 calc GR . . . .
H11H H -0.111719 0.512369 0.689022 0.073 Uiso 1 1 calc GR . . . .
H11I H -0.031954 0.590582 0.629623 0.073 Uiso 1 1 calc GR . . . .
C10 C -0.0981(8) 0.6988(13) 0.8126(8) 0.058(3) Uani 1 1 d . . . . .
H10A H -0.053417 0.748864 0.851262 0.087 Uiso 1 1 calc GR . . . .
H10B H -0.113005 0.598486 0.829748 0.087 Uiso 1 1 calc GR . . . .
H10C H -0.166560 0.751731 0.805930 0.087 Uiso 1 1 calc GR . . . .
C1S C 0.1206(12) 0.151(2) 0.9286(11) 0.086(5) Uani 1 1 d . . . . .
H1S H 0.164797 0.202944 0.968696 0.104 Uiso 1 1 calc R . . 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
Cl3 C1S 1.748(18) . ?
O5 C13" 1.439(7) . ?
O5 C12" 1.464(7) . ?
O2 C2' 1.368(8) . ?
O2 C9' 1.444(6) . ?
Cl2 C1S 1.737(18) . ?
O10 C7" 1.207(8) . ?
Cl1 C1S 1.772(19) . ?
O1 H1 0.8200 . ?
O1 C3 1.365(8) . ?
O1" C2" 1.318(9) . ?
O1" C10" 1.474(8) . ?
O6 C4" 1.429(8) . ?
O6 C3" 1.420(8) . ?
O8 C8" 1.427(8) . ?
O8 C14" 1.367(8) . ?
O4 H4 0.8200 . ?
O4 C10' 1.456(7) . ?
O3 C3' 1.380(8) . ?
O3 C8' 1.437(9) . ?
O9 C14" 1.193(9) . ?
O7 C2" 1.216(9) . ?
C1 C2 1.424(8) . ?
C1 C6 1.396(9) . ?
C1 C12" 1.516(9) . ?
C2 C3 1.367(9) . ?
C2 C13" 1.514(8) . ?
C6 C5 1.397(10) . ?
C6 C7 1.512(9) . ?
C1' C6' 1.404(9) . ?
C1' C2' 1.400(8) . ?
C1' C12" 1.493(8) . ?
C3 C4 1.408(9) . ?
C5' C6' 1.402(9) . ?
C5' C4' 1.380(10) . ?
C5' C7' 1.500(9) . ?
C7" C8" 1.539(8) . ?
C7" C6" 1.519(8) . ?
C2" C3" 1.491(10) . ?
C6' H6' 0.9300 . ?
C2' C3' 1.409(8) . ?
C8" H8" 0.9800 . ?
C8" C9" 1.540(9) . ?
C3' C4' 1.389(10) . ?
C5" H5" 0.9800 . ?
C5" C12" 1.570(7) . ?
C5" C6" 1.558(8) . ?
C5" C4" 1.516(8) . ?
C14" C15" 1.487(11) . ?
C13" H13" 0.9800 . ?
C13" C6" 1.572(7) . ?
C9' H9' 0.9800 . ?
C9' C10' 1.528(9) . ?
C9' C8' 1.507(9) . ?
C4 H4A 0.9300 . ?
C4 C5 1.391(10) . ?
C6" H6" 0.9800 . ?
C4" H4" 0.9800 . ?
C4" C3" 1.480(8) . ?
C10' C12' 1.523(9) . ?
C10' C11' 1.493(11) . ?
C3" H3" 0.9800 . ?
C5 H5 0.9300 . ?
C10" H10" 0.9800 . ?
C10" C9" 1.519(10) . ?
C10" C11" 1.515(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.505(10) . ?
C4' H4' 0.9300 . ?
C9" H9"A 0.9700 . ?
C9" H9"B 0.9700 . ?
C8' H8'A 0.9700 . ?
C8' H8'B 0.9700 . ?
C7' H7'A 0.9600 . ?
C7' H7'B 0.9600 . ?
C7' H7'C 0.9600 . ?
C8 H8 0.9300 . ?
C8 C9 1.350(11) . ?
C12' H12A 0.9600 . ?
C12' H12B 0.9600 . ?
C12' H12C 0.9600 . ?
C15" H15A 0.9600 . ?
C15" H15B 0.9600 . ?
C15" H15C 0.9600 . ?
C9 C11 1.481(15) . ?
C9 C10 1.528(14) . ?
C11' H11A 0.9600 . ?
C11' H11B 0.9600 . ?
C11' H11C 0.9600 . ?
C11" H11D 0.9600 . ?
C11" H11E 0.9600 . ?
C11" H11F 0.9600 . ?
C11 H11G 0.9600 . ?
C11 H11H 0.9600 . ?
C11 H11I 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C1S H1S 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13" O5 C12" 97.7(4) . . ?
C2' O2 C9' 115.9(5) . . ?
C3 O1 H1 109.5 . . ?
C2" O1" C10" 119.4(6) . . ?
C3" O6 C4" 62.6(4) . . ?
C14" O8 C8" 115.8(5) . . ?
C10' O4 H4 109.5 . . ?
C3' O3 C8' 112.7(5) . . ?
C2 C1 C12" 104.3(5) . . ?
C6 C1 C2 121.5(6) . . ?
C6 C1 C12" 134.2(6) . . ?
C1 C2 C13" 104.8(5) . . ?
C3 C2 C1 121.2(6) . . ?
C3 C2 C13" 133.9(5) . . ?
C1 C6 C5 116.3(6) . . ?
C1 C6 C7 125.8(6) . . ?
C5 C6 C7 117.9(6) . . ?
C6' C1' C12" 122.8(5) . . ?
C2' C1' C6' 118.2(5) . . ?
C2' C1' C12" 118.9(5) . . ?
O1 C3 C2 120.7(6) . . ?
O1 C3 C4 121.5(6) . . ?
C2 C3 C4 117.8(6) . . ?
C6' C5' C7' 120.2(6) . . ?
C4' C5' C6' 119.1(6) . . ?
C4' C5' C7' 120.7(6) . . ?
O10 C7" C8" 119.0(6) . . ?
O10 C7" C6" 120.9(5) . . ?
C6" C7" C8" 120.0(5) . . ?
O1" C2" C3" 112.7(6) . . ?
O7 C2" O1" 125.1(7) . . ?
O7 C2" C3" 122.2(7) . . ?
C1' C6' H6' 119.2 . . ?
C5' C6' C1' 121.6(6) . . ?
C5' C6' H6' 119.2 . . ?
O2 C2' C1' 117.6(5) . . ?
O2 C2' C3' 122.0(5) . . ?
C1' C2' C3' 120.4(6) . . ?
O8 C8" C7" 108.3(5) . . ?
O8 C8" H8" 109.3 . . ?
O8 C8" C9" 106.3(5) . . ?
C7" C8" H8" 109.3 . . ?
C9" C8" C7" 114.3(5) . . ?
C9" C8" H8" 109.3 . . ?
O3 C3' C2' 120.7(6) . . ?
O3 C3' C4' 119.5(6) . . ?
C4' C3' C2' 119.8(6) . . ?
C12" C5" H5" 108.0 . . ?
C6" C5" H5" 108.0 . . ?
C6" C5" C12" 102.0(4) . . ?
C4" C5" H5" 108.0 . . ?
C4" C5" C12" 112.6(5) . . ?
C4" C5" C6" 117.7(5) . . ?
O8 C14" C15" 111.0(6) . . ?
O9 C14" O8 122.5(7) . . ?
O9 C14" C15" 126.5(6) . . ?
O5 C13" C2 102.4(4) . . ?
O5 C13" H13" 115.1 . . ?
O5 C13" C6" 100.1(4) . . ?
C2 C13" H13" 115.1 . . ?
C2 C13" C6" 107.3(5) . . ?
C6" C13" H13" 115.1 . . ?
O5 C12" C1 102.1(4) . . ?
O5 C12" C1' 110.6(5) . . ?
O5 C12" C5" 99.7(4) . . ?
C1 C12" C5" 106.1(5) . . ?
C1' C12" C1 117.2(5) . . ?
C1' C12" C5" 118.6(5) . . ?
O2 C9' H9' 108.9 . . ?
O2 C9' C10' 105.8(5) . . ?
O2 C9' C8' 109.4(5) . . ?
C10' C9' H9' 108.9 . . ?
C8' C9' H9' 108.9 . . ?
C8' C9' C10' 114.7(6) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 C3 120.8(6) . . ?
C5 C4 H4A 119.6 . . ?
C7" C6" C5" 110.7(5) . . ?
C7" C6" C13" 110.8(5) . . ?
C7" C6" H6" 111.3 . . ?
C5" C6" C13" 101.0(4) . . ?
C5" C6" H6" 111.3 . . ?
C13" C6" H6" 111.3 . . ?
O6 C4" C5" 119.6(5) . . ?
O6 C4" H4" 114.3 . . ?
O6 C4" C3" 58.4(4) . . ?
C5" C4" H4" 114.3 . . ?
C3" C4" C5" 124.5(6) . . ?
C3" C4" H4" 114.3 . . ?
O4 C10' C9' 102.8(5) . . ?
O4 C10' C12' 109.4(5) . . ?
O4 C10' C11' 109.1(5) . . ?
C12' C10' C9' 110.0(5) . . ?
C11' C10' C9' 114.1(6) . . ?
C11' C10' C12' 111.1(6) . . ?
O6 C3" C2" 118.9(6) . . ?
O6 C3" C4" 59.0(4) . . ?
O6 C3" H3" 115.3 . . ?
C2" C3" H3" 115.3 . . ?
C4" C3" C2" 121.5(5) . . ?
C4" C3" H3" 115.3 . . ?
C6 C5 H5 118.8 . . ?
C4 C5 C6 122.3(6) . . ?
C4 C5 H5 118.8 . . ?
O1" C10" H10" 110.2 . . ?
O1" C10" C9" 102.8(5) . . ?
O1" C10" C11" 109.7(6) . . ?
C9" C10" H10" 110.2 . . ?
C11" C10" H10" 110.2 . . ?
C11" C10" C9" 113.7(7) . . ?
C6 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 C6 113.9(6) . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C5' C4' C3' 120.9(6) . . ?
C5' C4' H4' 119.5 . . ?
C3' C4' H4' 119.5 . . ?
C8" C9" H9"A 108.1 . . ?
C8" C9" H9"B 108.1 . . ?
C10" C9" C8" 116.6(6) . . ?
C10" C9" H9"A 108.1 . . ?
C10" C9" H9"B 108.1 . . ?
H9"A C9" H9"B 107.3 . . ?
O3 C8' C9' 110.1(6) . . ?
O3 C8' H8'A 109.6 . . ?
O3 C8' H8'B 109.6 . . ?
C9' C8' H8'A 109.6 . . ?
C9' C8' H8'B 109.6 . . ?
H8'A C8' H8'B 108.2 . . ?
C5' C7' H7'A 109.5 . . ?
C5' C7' H7'B 109.5 . . ?
C5' C7' H7'C 109.5 . . ?
H7'A C7' H7'B 109.5 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
C7 C8 H8 117.3 . . ?
C9 C8 C7 125.4(8) . . ?
C9 C8 H8 117.3 . . ?
C10' C12' H12A 109.5 . . ?
C10' C12' H12B 109.5 . . ?
C10' C12' H12C 109.5 . . ?
H12A C12' H12B 109.5 . . ?
H12A C12' H12C 109.5 . . ?
H12B C12' H12C 109.5 . . ?
C14" C15" H15A 109.5 . . ?
C14" C15" H15B 109.5 . . ?
C14" C15" H15C 109.5 . . ?
H15A C15" H15B 109.5 . . ?
H15A C15" H15C 109.5 . . ?
H15B C15" H15C 109.5 . . ?
C8 C9 C11 123.7(8) . . ?
C8 C9 C10 118.3(9) . . ?
C11 C9 C10 117.9(8) . . ?
C10' C11' H11A 109.5 . . ?
C10' C11' H11B 109.5 . . ?
C10' C11' H11C 109.5 . . ?
H11A C11' H11B 109.5 . . ?
H11A C11' H11C 109.5 . . ?
H11B C11' H11C 109.5 . . ?
C10" C11" H11D 109.5 . . ?
C10" C11" H11E 109.5 . . ?
C10" C11" H11F 109.5 . . ?
H11D C11" H11E 109.5 . . ?
H11D C11" H11F 109.5 . . ?
H11E C11" H11F 109.5 . . ?
C9 C11 H11G 109.5 . . ?
C9 C11 H11H 109.5 . . ?
C9 C11 H11I 109.5 . . ?
H11G C11 H11H 109.5 . . ?
H11G C11 H11I 109.5 . . ?
H11H C11 H11I 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Cl3 C1S Cl1 110.9(10) . . ?
Cl3 C1S H1S 107.3 . . ?
Cl2 C1S Cl3 110.5(11) . . ?
Cl2 C1S Cl1 113.3(8) . . ?
Cl2 C1S H1S 107.3 . . ?
Cl1 C1S H1S 107.3 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.438
_oxdiff_exptl_absorpt_empirical_full_min 0.519
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
