# Electronic Supplementary Material (ESI) for ChemComm.
# 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_eds_071903_0m
_database_code_depnum_ccdc_archive 'CCDC 1978089'
loop_
_audit_author_name
_audit_author_address
'Eric Sylvester'
;University at Buffalo
United States of America
;
_audit_update_record             
;
2020-01-15 deposited with the CCDC.	2020-12-07 downloaded from the CCDC.
;
_audit_creation_date             2019-07-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 Cl2 O2'
_chemical_formula_sum            'C23 H18 Cl2 O2'
_chemical_formula_weight         397.27
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.4867(5)
_cell_length_b                   12.1391(11)
_cell_length_c                   28.047(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1868.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6905
_cell_measurement_temperature    90
_cell_measurement_theta_max      26.266
_cell_measurement_theta_min      2.750
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_T_max  0.7138
_exptl_absorpt_correction_T_min  0.6053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1111 before and 0.0614 after correction. The Ratio of minimum to maximum transmission is 0.8480. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            19753
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.387
_diffrn_reflns_theta_min         1.828
_diffrn_ambient_temperature      90
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus rotating anode'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3428
_reflns_number_total             3809
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1297 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3809
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²+0.1270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0704
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C19(H19), C20(H20), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.07708(12) 1.14965(5) 0.50934(2) 0.01760(15) Uani 1 1 d . . . . .
Cl2 Cl -0.55140(14) -0.20685(5) 0.73185(2) 0.02686(18) Uani 1 1 d . . . . .
O1 O 0.3772(3) 0.50809(13) 0.61631(6) 0.0148(4) Uani 1 1 d . . . . .
O2 O 0.1287(3) 0.63316(13) 0.65693(6) 0.0200(4) Uani 1 1 d . . . . .
C1 C 0.8999(5) 1.03961(18) 0.52917(8) 0.0134(5) Uani 1 1 d . . . . .
C2 C 0.9767(5) 0.93238(19) 0.52019(8) 0.0152(5) Uani 1 1 d . . . . .
H2 H 1.122527 0.919034 0.502864 0.018 Uiso 1 1 calc R . . . .
C3 C 0.8373(5) 0.8452(2) 0.53692(8) 0.0154(5) Uani 1 1 d . . . . .
H3 H 0.889420 0.771784 0.531232 0.019 Uiso 1 1 calc R . . . .
C4 C 0.6207(5) 0.86399(19) 0.56207(8) 0.0137(5) Uani 1 1 d . . . . .
C5 C 0.5478(5) 0.97303(18) 0.57017(8) 0.0145(5) Uani 1 1 d . . . . .
H5 H 0.401243 0.987151 0.587155 0.017 Uiso 1 1 calc R . . . .
C6 C 0.6862(5) 1.0603(2) 0.55379(9) 0.0155(5) Uani 1 1 d . . . . .
H6 H 0.635016 1.133970 0.559400 0.019 Uiso 1 1 calc R . . . .
C7 C 0.4796(4) 0.77251(19) 0.57974(8) 0.0134(5) Uani 1 1 d . . . . .
C8 C 0.3642(5) 0.69565(19) 0.59401(9) 0.0149(5) Uani 1 1 d . . . . .
C9 C 0.2202(5) 0.60158(19) 0.61153(9) 0.0134(5) Uani 1 1 d . . . . .
C10 C 0.2078(4) 0.41840(19) 0.62619(9) 0.0142(5) Uani 1 1 d . . . . .
C11 C 0.1091(5) 0.4374(2) 0.67619(9) 0.0192(6) Uani 1 1 d . . . . .
H11A H 0.244521 0.435091 0.699486 0.023 Uiso 1 1 calc R . . . .
H11B H -0.007915 0.378294 0.684441 0.023 Uiso 1 1 calc R . . . .
C12 C -0.0181(5) 0.5492(2) 0.67874(9) 0.0224(6) Uani 1 1 d . . . . .
H12A H -0.177318 0.544908 0.662235 0.027 Uiso 1 1 calc R . . . .
H12B H -0.048696 0.568666 0.712493 0.027 Uiso 1 1 calc R . . . .
C13 C 0.0181(5) 0.55984(19) 0.57787(9) 0.0161(5) Uani 1 1 d . . . . .
H13A H 0.058935 0.575390 0.544157 0.019 Uiso 1 1 calc R . . . .
H13B H -0.140499 0.594468 0.585559 0.019 Uiso 1 1 calc R . . . .
C14 C 0.0113(4) 0.43427(19) 0.58747(8) 0.0150(5) Uani 1 1 d . . . . .
H14A H -0.150947 0.410965 0.599142 0.018 Uiso 1 1 calc R . . . .
H14B H 0.051783 0.392087 0.558319 0.018 Uiso 1 1 calc R . . . .
C15 C 0.3542(5) 0.31215(19) 0.62149(10) 0.0179(6) Uani 1 1 d . . . . .
H15A H 0.411139 0.304129 0.588173 0.022 Uiso 1 1 calc R . . . .
H15B H 0.499486 0.316192 0.642347 0.022 Uiso 1 1 calc R . . . .
C16 C 0.2073(5) 0.2150(2) 0.63471(8) 0.0157(6) Uani 1 1 d . . . . .
C17 C 0.0842(5) 0.14019(19) 0.64784(8) 0.0160(5) Uani 1 1 d . . . . .
C18 C -0.0703(5) 0.05402(18) 0.66662(8) 0.0136(5) Uani 1 1 d . . . . .
C19 C -0.0099(5) -0.05741(19) 0.66298(8) 0.0163(6) Uani 1 1 d . . . . .
H19 H 0.135077 -0.078474 0.646870 0.020 Uiso 1 1 calc R . . . .
C20 C -0.1591(5) -0.1376(2) 0.68260(9) 0.0175(6) Uani 1 1 d . . . . .
H20 H -0.117144 -0.213355 0.680096 0.021 Uiso 1 1 calc R . . . .
C21 C -0.3689(5) -0.10600(19) 0.70575(9) 0.0168(6) Uani 1 1 d . . . . .
C22 C -0.4352(5) 0.00389(19) 0.70983(8) 0.0177(5) Uani 1 1 d . . . . .
H22 H -0.580512 0.024267 0.726000 0.021 Uiso 1 1 calc R . . . .
C23 C -0.2857(5) 0.08314(19) 0.68991(9) 0.0163(6) Uani 1 1 d . . . . .
H23 H -0.330203 0.158601 0.692115 0.020 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.743(2) . ?
Cl2 C21 1.743(2) . ?
O1 C9 1.431(3) . ?
O1 C10 1.458(3) . ?
O2 C9 1.421(3) . ?
O2 C12 1.435(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.384(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.401(4) . ?
C4 C5 1.401(3) . ?
C4 C7 1.442(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.197(3) . ?
C8 C9 1.473(3) . ?
C9 C13 1.542(3) . ?
C10 C11 1.521(4) . ?
C10 C14 1.542(3) . ?
C10 C15 1.525(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.528(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.548(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.476(3) . ?
C16 C17 1.190(4) . ?
C17 C18 1.446(3) . ?
C18 C19 1.396(3) . ?
C18 C23 1.396(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.377(4) . ?
C21 C22 1.387(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.382(3) . ?
C23 H23 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
C9 O1 C10 103.09(18) . . ?
C9 O2 C12 112.86(18) . . ?
C2 C1 Cl1 119.3(2) . . ?
C6 C1 Cl1 119.50(18) . . ?
C6 C1 C2 121.1(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 118.5(2) . . ?
C3 C4 C7 120.2(2) . . ?
C5 C4 C7 121.2(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C4 179.1(3) . . ?
C7 C8 C9 179.5(3) . . ?
O1 C9 C8 108.9(2) . . ?
O1 C9 C13 103.28(19) . . ?
O2 C9 O1 110.03(19) . . ?
O2 C9 C8 106.21(19) . . ?
O2 C9 C13 112.5(2) . . ?
C8 C9 C13 115.9(2) . . ?
O1 C10 C11 106.8(2) . . ?
O1 C10 C14 102.61(18) . . ?
O1 C10 C15 106.24(19) . . ?
C11 C10 C14 112.4(2) . . ?
C11 C10 C15 113.3(2) . . ?
C15 C10 C14 114.4(2) . . ?
C10 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
C10 C11 C12 109.9(2) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
O2 C12 C11 110.8(2) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C9 C13 H13A 111.1 . . ?
C9 C13 H13B 111.1 . . ?
C9 C13 C14 103.54(19) . . ?
H13A C13 H13B 109.0 . . ?
C14 C13 H13A 111.1 . . ?
C14 C13 H13B 111.1 . . ?
C10 C14 C13 103.23(19) . . ?
C10 C14 H14A 111.1 . . ?
C10 C14 H14B 111.1 . . ?
C13 C14 H14A 111.1 . . ?
C13 C14 H14B 111.1 . . ?
H14A C14 H14B 109.1 . . ?
C10 C15 H15A 109.3 . . ?
C10 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C10 111.5(2) . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C17 C16 C15 175.9(3) . . ?
C16 C17 C18 176.0(3) . . ?
C19 C18 C17 122.4(2) . . ?
C23 C18 C17 118.9(2) . . ?
C23 C18 C19 118.7(2) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.8(2) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 120.5 . . ?
C21 C20 C19 119.0(2) . . ?
C21 C20 H20 120.5 . . ?
C20 C21 Cl2 118.85(19) . . ?
C20 C21 C22 121.8(2) . . ?
C22 C21 Cl2 119.4(2) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 C21 118.7(2) . . ?
C23 C22 H22 120.6 . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 121.0(2) . . ?
C22 C23 H23 119.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_asb-achiralketal-biphenyl
_database_code_depnum_ccdc_archive 'CCDC 2020673'
loop_
_audit_author_name
_audit_author_address
'Eric Sylvester'
;State University of New York, Buffalo
United States of America
;
_audit_update_record             
;
2020-07-31 deposited with the CCDC.	2020-12-07 downloaded from the CCDC.
;
_audit_creation_date             2020-07-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H28 O2'
_chemical_formula_sum            'C31 H28 O2'
_chemical_formula_weight         432.53
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.015(2)
_cell_length_b                   9.4761(9)
_cell_length_c                   17.0238(18)
_cell_angle_alpha                90
_cell_angle_beta                 95.826(6)
_cell_angle_gamma                90
_cell_volume                     2249.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6747
_cell_measurement_temperature    90
_cell_measurement_theta_max      26.398
_cell_measurement_theta_min      2.405
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.997
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) was 0.1751 before and 0.0450 after correction. The Ratio of minimum to maximum transmission is 0.9469. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1985
_diffrn_reflns_av_unetI/netI     0.1030
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21398
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.403
_diffrn_reflns_theta_min         1.795
_diffrn_ambient_temperature      90.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3661
_reflns_number_total             4604
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL n/a (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4604
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0593
_refine_ls_restrained_S_all      1.078
_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)+(0.0181P)²+1.2055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.1662
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 C6B, C6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C6B \\sim C5B \\sim C5 \\sim C6: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.08 within 1.7A
Uanis(C6B) = Uanis(C6)
Uanis(C2) = Uanis(C2B)
Uanis(O2) = Uanis(O2B)
Uanis(C6B) = Uanis(C2B) = Uanis(C3B) = Uanis(C5B)
Uanis(C6B) = Uanis(C5B) = Uanis(C2B) = Uanis(C3B)
4. Others
 Sof(O1B)=Sof(O2B)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(C3B)=Sof(H3BA)=Sof(H3BB)=
 Sof(C6B)=Sof(H7BA)=Sof(H7BB)=Sof(C5B)=Sof(H8BA)=Sof(H8BB)=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C5)=
 Sof(H5A)=Sof(H5B)=Sof(C6)=Sof(H6A)=Sof(H6B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C2B(H2BA,H2BB), C3B(H3BA,H3BB), C6B(H7BA,H7BB), C5B(H8BA,H8BB),
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C1 C 0.65709(13) 0.6843(2) 0.75318(11) 0.0204(5) Uani 1 1 d . . . . .
C4 C 0.77154(14) 0.6700(2) 0.66845(11) 0.0215(5) Uani 1 1 d . . . . .
C7 C 0.64250(13) 0.7073(2) 0.83978(10) 0.0153(4) Uani 1 1 d . . . . .
H7A H 0.677731 0.633121 0.871785 0.018 Uiso 1 1 calc R U . . .
H7B H 0.670586 0.799516 0.856891 0.018 Uiso 1 1 calc R U . . .
C8 C 0.53825(13) 0.7046(2) 0.85629(10) 0.0147(4) Uani 1 1 d . . . . .
C9 C 0.47980(13) 0.8221(2) 0.84154(10) 0.0159(4) Uani 1 1 d . . . . .
H9 H 0.505908 0.905922 0.821842 0.019 Uiso 1 1 calc R U . . .
C10 C 0.38346(13) 0.8187(2) 0.85520(11) 0.0163(4) Uani 1 1 d . . . . .
H10 H 0.344688 0.899796 0.843728 0.020 Uiso 1 1 calc R U . . .
C11 C 0.34302(13) 0.6988(2) 0.88535(10) 0.0144(4) Uani 1 1 d . . . . .
C12 C 0.40205(13) 0.5815(2) 0.90167(11) 0.0176(4) Uani 1 1 d . . . . .
H12 H 0.376440 0.498730 0.923036 0.021 Uiso 1 1 calc R U . . .
C13 C 0.49831(13) 0.5843(2) 0.88696(11) 0.0186(4) Uani 1 1 d . . . . .
H13 H 0.537120 0.503156 0.898018 0.022 Uiso 1 1 calc R U . . .
C14 C 0.23933(13) 0.6961(2) 0.90008(10) 0.0148(4) Uani 1 1 d . . . . .
C15 C 0.19128(13) 0.8196(2) 0.91644(10) 0.0161(4) Uani 1 1 d . . . . .
H15 H 0.224833 0.906854 0.919098 0.019 Uiso 1 1 calc R U . . .
C16 C 0.09415(14) 0.8168(2) 0.92903(11) 0.0185(4) Uani 1 1 d . . . . .
H16 H 0.061957 0.902022 0.939299 0.022 Uiso 1 1 calc R U . . .
C17 C 0.04503(14) 0.6902(2) 0.92655(11) 0.0210(4) Uani 1 1 d . . . . .
H17 H -0.020617 0.688042 0.935963 0.025 Uiso 1 1 calc R U . . .
C18 C 0.09163(14) 0.5666(2) 0.91033(12) 0.0234(5) Uani 1 1 d . . . . .
H18 H 0.057794 0.479637 0.908392 0.028 Uiso 1 1 calc R U . . .
C19 C 0.18813(13) 0.5691(2) 0.89679(11) 0.0194(4) Uani 1 1 d . . . . .
H19 H 0.219389 0.483773 0.885220 0.023 Uiso 1 1 calc R U . . .
C20 C 0.87641(13) 0.6771(2) 0.65639(11) 0.0159(4) Uani 1 1 d . . . . .
C21 C 0.90413(13) 0.6552(2) 0.58127(10) 0.0178(4) Uani 1 1 d . . . . .
H21 H 0.856924 0.635804 0.538561 0.021 Uiso 1 1 calc R U . . .
C22 C 0.99989(13) 0.6614(2) 0.56809(10) 0.0159(4) Uani 1 1 d . . . . .
H22 H 1.017602 0.645584 0.516413 0.019 Uiso 1 1 calc R U . . .
C23 C 1.07124(13) 0.69076(19) 0.62989(10) 0.0142(4) Uani 1 1 d . . . . .
C24 C 1.04266(13) 0.7135(2) 0.70496(10) 0.0159(4) Uani 1 1 d . . . . .
H24 H 1.089464 0.734563 0.747699 0.019 Uiso 1 1 calc R U . . .
C25 C 0.94643(13) 0.7058(2) 0.71798(10) 0.0163(4) Uani 1 1 d . . . . .
H25 H 0.928375 0.720410 0.769664 0.020 Uiso 1 1 calc R U . . .
C26 C 1.17436(13) 0.69399(19) 0.61546(11) 0.0144(4) Uani 1 1 d . . . . .
C27 C 1.20133(13) 0.7155(2) 0.53973(11) 0.0174(4) Uani 1 1 d . . . . .
H27 H 1.153242 0.730244 0.497045 0.021 Uiso 1 1 calc R U . . .
C28 C 1.29719(13) 0.7156(2) 0.52557(11) 0.0186(4) Uani 1 1 d . . . . .
H28 H 1.313913 0.730321 0.473490 0.022 Uiso 1 1 calc R U . . .
C29 C 1.36865(14) 0.6944(2) 0.58694(12) 0.0194(4) Uani 1 1 d . . . . .
H29 H 1.434196 0.693785 0.577182 0.023 Uiso 1 1 calc R U . . .
C30 C 1.34325(13) 0.6743(2) 0.66257(11) 0.0194(4) Uani 1 1 d . . . . .
H30 H 1.391711 0.660633 0.705106 0.023 Uiso 1 1 calc R U . . .
C31 C 1.24720(13) 0.6738(2) 0.67676(11) 0.0171(4) Uani 1 1 d . . . . .
H31 H 1.230891 0.659487 0.728991 0.021 Uiso 1 1 calc R U . . .
O1B O 0.7611(9) 0.7347(14) 0.7475(7) 0.017(3) Uani 0.142(2) 1 d . . P A 2
O2B O 0.7463(7) 0.8363(11) 0.6238(6) 0.0157(4) Uani 0.142(2) 1 d . . P A 2
C2B C 0.6132(10) 0.8562(16) 0.7086(8) 0.0151(4) Uani 0.142(2) 1 d . . P A 2
H2BA H 0.542462 0.861288 0.706639 0.018 Uiso 0.142(2) 1 calc R U P A 2
H2BB H 0.640813 0.935762 0.741109 0.018 Uiso 0.142(2) 1 calc R U P A 2
C3B C 0.6439(9) 0.8659(14) 0.6256(7) 0.0151(4) Uani 0.142(2) 1 d . . P A 2
H3BA H 0.606136 0.797695 0.591065 0.018 Uiso 0.142(2) 1 calc R U P A 2
H3BB H 0.629731 0.961724 0.604434 0.018 Uiso 0.142(2) 1 calc R U P A 2
C6B C 0.6314(10) 0.5890(16) 0.6991(8) 0.0151(4) Uani 0.142(2) 1 d . U P A 2
H7BA H 0.568855 0.614666 0.670387 0.018 Uiso 0.142(2) 1 calc R U P A 2
H7BB H 0.624798 0.495703 0.724178 0.018 Uiso 0.142(2) 1 calc R U P A 2
C5B C 0.7060(11) 0.5826(17) 0.6436(8) 0.0151(4) Uani 0.142(2) 1 d . U P A 2
H8BA H 0.732630 0.485978 0.642097 0.018 Uiso 0.142(2) 1 calc R U P A 2
H8BB H 0.678337 0.608429 0.589669 0.018 Uiso 0.142(2) 1 calc R U P A 2
O1 O 0.76024(13) 0.6631(2) 0.75071(11) 0.0132(4) Uani 0.858(2) 1 d . . P A 1
O2 O 0.73779(11) 0.53640(18) 0.63339(9) 0.0157(4) Uani 0.858(2) 1 d . . P A 1
C2 C 0.61180(16) 0.5416(3) 0.72261(13) 0.0151(4) Uani 0.858(2) 1 d . . P A 1
H2A H 0.635968 0.464040 0.758171 0.018 Uiso 0.858(2) 1 calc R U P A 1
H2B H 0.541208 0.545983 0.722462 0.018 Uiso 0.858(2) 1 calc R U P A 1
C3 C 0.63759(15) 0.5129(2) 0.63959(13) 0.0175(5) Uani 0.858(2) 1 d . . P A 1
H3A H 0.621300 0.414030 0.625105 0.021 Uiso 0.858(2) 1 calc R U P A 1
H3B H 0.599228 0.575398 0.601942 0.021 Uiso 0.858(2) 1 calc R U P A 1
C5 C 0.70903(17) 0.7923(3) 0.63801(12) 0.0154(5) Uani 0.858(2) 1 d . U P A 1
H5A H 0.678363 0.772943 0.584114 0.019 Uiso 0.858(2) 1 calc R U P A 1
H5B H 0.746966 0.880297 0.637109 0.019 Uiso 0.858(2) 1 calc R U P A 1
C6 C 0.63317(16) 0.8037(3) 0.69746(13) 0.0151(4) Uani 0.858(2) 1 d . U P A 1
H6A H 0.638122 0.895390 0.725506 0.018 Uiso 0.858(2) 1 calc R U P A 1
H6B H 0.567539 0.793541 0.670517 0.018 Uiso 0.858(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
C1 C7 1.525(2) . ?
C1 O1B 1.547(12) . ?
C1 C2B 1.874(15) . ?
C1 C6B 1.314(14) . ?
C1 O1 1.464(3) . ?
C1 C2 1.560(3) . ?
C1 C6 1.493(3) . ?
C4 C20 1.506(3) . ?
C4 O1B 1.499(12) . ?
C4 O2B 1.770(11) . ?
C4 C5B 1.277(15) . ?
C4 O1 1.427(3) . ?
C4 O2 1.458(3) . ?
C4 C5 1.512(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.516(2) . ?
C8 C9 1.390(3) . ?
C8 C13 1.394(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(3) . ?
C11 C12 1.396(3) . ?
C11 C14 1.500(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.397(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(3) . ?
C14 C19 1.400(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.400(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.382(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.395(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(3) . ?
C20 C25 1.388(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.404(2) . ?
C23 C24 1.394(3) . ?
C23 C26 1.491(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.391(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.395(3) . ?
C26 C31 1.397(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.389(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.386(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.383(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.392(3) . ?
C31 H31 0.9500 . ?
O2B C3B 1.466(15) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C2B C3B 1.521(18) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C6B H7BA 0.9900 . ?
C6B H7BB 0.9900 . ?
C6B C5B 1.48(2) . ?
C5B H8BA 0.9900 . ?
C5B H8BB 0.9900 . ?
O2 C3 1.436(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.518(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.544(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

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
C7 C1 O1B 103.7(5) . . ?
C7 C1 C2B 101.3(5) . . ?
C7 C1 C2 110.89(17) . . ?
O1B C1 C2B 88.8(7) . . ?
C6B C1 C7 136.2(7) . . ?
C6B C1 O1B 111.2(8) . . ?
C6B C1 C2B 105.0(8) . . ?
O1 C1 C7 106.09(15) . . ?
O1 C1 C2 103.93(16) . . ?
O1 C1 C6 104.16(17) . . ?
C6 C1 C7 117.55(18) . . ?
C6 C1 C2 112.80(17) . . ?
C20 C4 O2B 93.2(4) . . ?
C20 C4 C5 117.28(18) . . ?
O1B C4 C20 106.8(5) . . ?
O1B C4 O2B 89.3(6) . . ?
C5B C4 C20 131.6(8) . . ?
C5B C4 O1B 115.5(8) . . ?
C5B C4 O2B 109.2(7) . . ?
O1 C4 C20 110.06(15) . . ?
O1 C4 O2 107.35(17) . . ?
O1 C4 C5 104.68(17) . . ?
O2 C4 C20 105.29(16) . . ?
O2 C4 C5 111.88(16) . . ?
C1 C7 H7A 108.8 . . ?
C1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 C1 113.79(14) . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C9 C8 C7 120.96(17) . . ?
C9 C8 C13 118.08(17) . . ?
C13 C8 C7 120.96(17) . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 120.98(17) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.22(17) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 117.92(17) . . ?
C10 C11 C14 120.87(16) . . ?
C12 C11 C14 121.21(17) . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.81(18) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 120.98(17) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C11 121.08(17) . . ?
C15 C14 C19 118.31(17) . . ?
C19 C14 C11 120.60(16) . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.83(18) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.07(18) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.84(19) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.30(19) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.64(18) . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C4 119.13(16) . . ?
C25 C20 C4 122.04(17) . . ?
C25 C20 C21 118.83(17) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.61(16) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 119.5 . . ?
C21 C22 C23 121.03(17) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C26 120.62(16) . . ?
C24 C23 C22 117.94(17) . . ?
C24 C23 C26 121.42(16) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.76(16) . . ?
C25 C24 H24 119.6 . . ?
C20 C25 C24 120.83(17) . . ?
C20 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C27 C26 C23 120.90(16) . . ?
C27 C26 C31 117.67(17) . . ?
C31 C26 C23 121.42(17) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 C26 121.22(17) . . ?
C28 C27 H27 119.4 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.43(17) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 120.4 . . ?
C30 C29 C28 119.14(18) . . ?
C30 C29 H29 120.4 . . ?
C29 C30 H30 119.8 . . ?
C29 C30 C31 120.45(17) . . ?
C31 C30 H30 119.8 . . ?
C26 C31 H31 119.5 . . ?
C30 C31 C26 121.08(17) . . ?
C30 C31 H31 119.5 . . ?
C4 O1B C1 96.2(6) . . ?
C3B O2B C4 108.3(8) . . ?
C1 C2B H2BA 110.0 . . ?
C1 C2B H2BB 110.0 . . ?
H2BA C2B H2BB 108.4 . . ?
C3B C2B C1 108.4(10) . . ?
C3B C2B H2BA 110.0 . . ?
C3B C2B H2BB 110.0 . . ?
O2B C3B C2B 112.2(10) . . ?
O2B C3B H3BA 109.2 . . ?
O2B C3B H3BB 109.2 . . ?
C2B C3B H3BA 109.2 . . ?
C2B C3B H3BB 109.2 . . ?
H3BA C3B H3BB 107.9 . . ?
C1 C6B H7BA 110.0 . . ?
C1 C6B H7BB 110.0 . . ?
C1 C6B C5B 108.4(11) . . ?
H7BA C6B H7BB 108.4 . . ?
C5B C6B H7BA 110.0 . . ?
C5B C6B H7BB 110.0 . . ?
C4 C5B C6B 107.0(12) . . ?
C4 C5B H8BA 110.3 . . ?
C4 C5B H8BB 110.3 . . ?
C6B C5B H8BA 110.3 . . ?
C6B C5B H8BB 110.3 . . ?
H8BA C5B H8BB 108.6 . . ?
C4 O1 C1 103.30(15) . . ?
C3 O2 C4 112.54(16) . . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 C1 109.78(19) . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
O2 C3 C2 111.56(17) . . ?
O2 C3 H3A 109.3 . . ?
O2 C3 H3B 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C4 C5 H5A 110.9 . . ?
C4 C5 H5B 110.9 . . ?
C4 C5 C6 104.05(18) . . ?
H5A C5 H5B 109.0 . . ?
C6 C5 H5A 110.9 . . ?
C6 C5 H5B 110.9 . . ?
C1 C6 C5 103.77(18) . . ?
C1 C6 H6A 111.0 . . ?
C1 C6 H6B 111.0 . . ?
C5 C6 H6A 111.0 . . ?
C5 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?

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
C1 C7 C8 C9 -80.2(2) . . . . ?
C1 C7 C8 C13 100.0(2) . . . . ?
C1 C2B C3B O2B -50.5(13) . . . . ?
C1 C6B C5B C4 1.6(15) . . . . ?
C1 C2 C3 O2 46.6(2) . . . . ?
C4 C20 C21 C22 179.82(18) . . . . ?
C4 C20 C25 C24 -179.19(18) . . . . ?
C4 O2B C3B C2B 54.6(12) . . . . ?
C4 O2 C3 C2 -47.6(2) . . . . ?
C4 C5 C6 C1 -2.4(2) . . . . ?
C7 C1 O1B C4 165.6(5) . . . . ?
C7 C1 C2B C3B 166.9(8) . . . . ?
C7 C1 C6B C5B -150.0(8) . . . . ?
C7 C1 O1 C4 -169.06(17) . . . . ?
C7 C1 C2 C3 -173.23(16) . . . . ?
C7 C1 C6 C5 144.68(17) . . . . ?
C7 C8 C9 C10 178.69(16) . . . . ?
C7 C8 C13 C12 -179.55(16) . . . . ?
C8 C9 C10 C11 1.2(3) . . . . ?
C9 C8 C13 C12 0.7(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C9 C10 C11 C14 179.83(16) . . . . ?
C10 C11 C12 C13 -0.9(3) . . . . ?
C10 C11 C14 C15 -27.1(3) . . . . ?
C10 C11 C14 C19 152.13(18) . . . . ?
C11 C12 C13 C8 0.6(3) . . . . ?
C11 C14 C15 C16 179.08(16) . . . . ?
C11 C14 C19 C18 -179.87(16) . . . . ?
C12 C11 C14 C15 152.61(17) . . . . ?
C12 C11 C14 C19 -28.1(3) . . . . ?
C13 C8 C9 C10 -1.5(3) . . . . ?
C14 C11 C12 C13 179.31(16) . . . . ?
C14 C15 C16 C17 1.0(3) . . . . ?
C15 C14 C19 C18 -0.6(3) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C17 C18 C19 C14 0.6(3) . . . . ?
C19 C14 C15 C16 -0.2(3) . . . . ?
C20 C4 O1B C1 -167.9(4) . . . . ?
C20 C4 O2B C3B -179.7(7) . . . . ?
C20 C4 C5B C6B 155.9(7) . . . . ?
C20 C4 O1 C1 169.47(17) . . . . ?
C20 C4 O2 C3 -179.75(15) . . . . ?
C20 C4 C5 C6 -146.77(18) . . . . ?
C20 C21 C22 C23 -0.4(3) . . . . ?
C21 C20 C25 C24 0.4(3) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C21 C22 C23 C26 178.60(17) . . . . ?
C22 C23 C24 C25 0.7(3) . . . . ?
C22 C23 C26 C27 21.7(3) . . . . ?
C22 C23 C26 C31 -157.43(18) . . . . ?
C23 C24 C25 C20 -0.8(3) . . . . ?
C23 C26 C27 C28 -178.62(17) . . . . ?
C23 C26 C31 C30 178.76(17) . . . . ?
C24 C23 C26 C27 -159.74(19) . . . . ?
C24 C23 C26 C31 21.2(3) . . . . ?
C25 C20 C21 C22 0.2(3) . . . . ?
C26 C23 C24 C25 -177.97(17) . . . . ?
C26 C27 C28 C29 -0.1(3) . . . . ?
C27 C26 C31 C30 -0.4(3) . . . . ?
C27 C28 C29 C30 -0.5(3) . . . . ?
C28 C29 C30 C31 0.6(3) . . . . ?
C29 C30 C31 C26 -0.2(3) . . . . ?
C31 C26 C27 C28 0.5(3) . . . . ?
O1B C1 C7 C8 163.8(5) . . . . ?
O1B C1 C2B C3B 63.2(10) . . . . ?
O1B C1 C6B C5B -9.6(13) . . . . ?
O1B C4 C20 C21 -165.1(5) . . . . ?
O1B C4 C20 C25 14.5(6) . . . . ?
O1B C4 O2B C3B -73.0(8) . . . . ?
O1B C4 C5B C6B 7.6(14) . . . . ?
O2B C4 C20 C21 -74.9(4) . . . . ?
O2B C4 C20 C25 104.7(3) . . . . ?
O2B C4 O1B C1 99.0(7) . . . . ?
O2B C4 C5B C6B -91.2(11) . . . . ?
C2B C1 C7 C8 72.3(5) . . . . ?
C2B C1 O1B C4 -93.0(7) . . . . ?
C2B C1 C6B C5B 85.0(11) . . . . ?
C6B C1 C7 C8 -53.9(9) . . . . ?
C6B C1 O1B C4 12.6(11) . . . . ?
C6B C1 C2B C3B -48.4(11) . . . . ?
C5B C4 C20 C21 44.6(9) . . . . ?
C5B C4 C20 C25 -135.9(9) . . . . ?
C5B C4 O1B C1 -12.1(12) . . . . ?
C5B C4 O2B C3B 43.9(11) . . . . ?
O1 C1 C7 C8 -169.38(16) . . . . ?
O1 C1 C2 C3 -59.6(2) . . . . ?
O1 C1 C6 C5 27.7(2) . . . . ?
O1 C4 C20 C21 166.82(19) . . . . ?
O1 C4 C20 C25 -13.6(3) . . . . ?
O1 C4 O2 C3 63.0(2) . . . . ?
O1 C4 C5 C6 -24.5(2) . . . . ?
O2 C4 C20 C21 51.4(2) . . . . ?
O2 C4 C20 C25 -129.00(18) . . . . ?
O2 C4 O1 C1 -76.4(2) . . . . ?
O2 C4 C5 C6 91.44(19) . . . . ?
C2 C1 C7 C8 -57.2(2) . . . . ?
C2 C1 O1 C4 74.0(2) . . . . ?
C2 C1 C6 C5 -84.4(2) . . . . ?
C5 C4 C20 C21 -73.7(2) . . . . ?
C5 C4 C20 C25 105.9(2) . . . . ?
C5 C4 O1 C1 42.6(2) . . . . ?
C5 C4 O2 C3 -51.3(2) . . . . ?
C6 C1 C7 C8 74.7(2) . . . . ?
C6 C1 O1 C4 -44.4(2) . . . . ?
C6 C1 C2 C3 52.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
