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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_dd18232_0m
_database_code_depnum_ccdc_archive 'CCDC 1977532'
loop_
_audit_author_name
_audit_author_address
' Shanghai Institute of Organic Chemistry'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2020-01-14 deposited with the CCDC.	2020-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
(R)-2-((2-chlorophenyl)(3,5-di-tert-butyl-4-hydroxyphenyl)methyl)-4-methyl-3-phenylisoxazol-5(2H)-one
_chemical_name_common            'N-diarylmethane substituted isoxazolinones'
_chemical_melting_point          410
_chemical_formula_moiety         chlorophenyl?phenylisoxazol
_chemical_formula_sum            'C31 H34 Cl N O3'
_chemical_formula_weight         504.04

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'
N N 0.0061 0.0033 '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'

_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'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   10.3478(10)
_cell_length_b                   14.7058(14)
_cell_length_c                   18.6178(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2833.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6763
_cell_measurement_theta_min      4.503
_cell_measurement_theta_max      54.719

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.166
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6443
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14349
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.590
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5529
_reflns_number_gt                4641
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          no
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²+0.4494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.038(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1717 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.06(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5529
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.60656(8) 0.64614(8) 0.87756(4) 0.0709(3) Uani 1 1 d . . . . .
O1 O 1.0766(3) 0.64428(17) 0.58123(12) 0.0736(7) Uani 1 1 d . . . . .
O2 O 0.99034(19) 0.62644(13) 0.69074(9) 0.0460(5) Uani 1 1 d . . . . .
O3 O 0.5617(3) 0.84008(14) 0.57460(11) 0.0658(7) Uani 1 1 d . . . . .
H3 H 0.5655 0.8199 0.5336 0.099 Uiso 1 1 calc R U . . .
N1 N 0.9207(2) 0.55635(14) 0.72706(11) 0.0396(5) Uani 1 1 d . . . . .
C1 C 1.0130(3) 0.5971(2) 0.62137(16) 0.0516(7) Uani 1 1 d . . . . .
C2 C 0.9556(3) 0.5095(2) 0.61353(15) 0.0526(8) Uani 1 1 d . . . . .
C3 C 0.8980(3) 0.48843(17) 0.67644(14) 0.0409(6) Uani 1 1 d . . . . .
C4 C 0.8289(3) 0.40657(18) 0.69971(15) 0.0426(6) Uani 1 1 d . . . . .
C5 C 0.7412(3) 0.3649(2) 0.65464(17) 0.0570(8) Uani 1 1 d . . . . .
H5 H 0.7266 0.3885 0.6090 0.068 Uiso 1 1 calc R U . . .
C6 C 0.6751(4) 0.2888(2) 0.6767(2) 0.0733(10) Uani 1 1 d . . . . .
H6 H 0.6162 0.2614 0.6458 0.088 Uiso 1 1 calc R U . . .
C7 C 0.6953(4) 0.2530(2) 0.7437(2) 0.0752(11) Uani 1 1 d . . . . .
H7 H 0.6492 0.2020 0.7585 0.090 Uiso 1 1 calc R U . . .
C8 C 0.7842(4) 0.2926(2) 0.7890(2) 0.0692(10) Uani 1 1 d . . . . .
H8 H 0.7998 0.2676 0.8341 0.083 Uiso 1 1 calc R U . . .
C9 C 0.8498(3) 0.3692(2) 0.76735(17) 0.0554(8) Uani 1 1 d . . . . .
H9 H 0.9089 0.3964 0.7983 0.066 Uiso 1 1 calc R U . . .
C10 C 0.9713(5) 0.4551(3) 0.54607(19) 0.0903(14) Uani 1 1 d . . . . .
H10A H 0.9491 0.3928 0.5553 0.135 Uiso 1 1 calc R U . . .
H10B H 1.0594 0.4586 0.5302 0.135 Uiso 1 1 calc R U . . .
H10C H 0.9155 0.4791 0.5095 0.135 Uiso 1 1 calc R U . . .
C11 C 0.8097(3) 0.59840(17) 0.76620(13) 0.0378(6) Uani 1 1 d . . . . .
H11 H 0.7503 0.5488 0.7782 0.045 Uiso 1 1 calc R U . . .
C12 C 0.8577(3) 0.63716(18) 0.83712(14) 0.0398(6) Uani 1 1 d . . . . .
C13 C 0.9876(3) 0.6481(2) 0.85203(15) 0.0542(8) Uani 1 1 d . . . . .
H13 H 1.0484 0.6335 0.8171 0.065 Uiso 1 1 calc R U . . .
C14 C 1.0289(4) 0.6805(3) 0.91810(18) 0.0712(10) Uani 1 1 d . . . . .
H14 H 1.1168 0.6865 0.9272 0.085 Uiso 1 1 calc R U . . .
C15 C 0.9417(4) 0.7037(3) 0.96972(17) 0.0697(10) Uani 1 1 d . . . . .
H15 H 0.9701 0.7257 1.0138 0.084 Uiso 1 1 calc R U . . .
C16 C 0.8119(4) 0.6946(2) 0.95646(16) 0.0617(9) Uani 1 1 d . . . . .
H16 H 0.7519 0.7112 0.9913 0.074 Uiso 1 1 calc R U . . .
C17 C 0.7711(3) 0.66081(19) 0.89132(14) 0.0460(7) Uani 1 1 d . . . . .
C18 C 0.7356(3) 0.66346(17) 0.71834(13) 0.0378(6) Uani 1 1 d . . . . .
C19 C 0.7438(3) 0.75710(18) 0.72690(14) 0.0411(6) Uani 1 1 d . . . . .
H19 H 0.7924 0.7806 0.7646 0.049 Uiso 1 1 calc R U . . .
C20 C 0.6810(3) 0.81663(17) 0.68032(14) 0.0405(6) Uani 1 1 d . . . . .
C21 C 0.6150(3) 0.77850(19) 0.62139(14) 0.0431(6) Uani 1 1 d . . . . .
C22 C 0.5992(3) 0.68428(18) 0.61300(13) 0.0409(6) Uani 1 1 d . . . . .
C23 C 0.6616(3) 0.62928(18) 0.66302(14) 0.0407(6) Uani 1 1 d . . . . .
H23 H 0.6530 0.5665 0.6589 0.049 Uiso 1 1 calc R U . . .
C24 C 0.5224(3) 0.6399(2) 0.55125(14) 0.0488(7) Uani 1 1 d . . . . .
C25 C 0.4894(7) 0.5422(3) 0.5671(3) 0.128(2) Uani 1 1 d . . . . .
H25A H 0.5676 0.5077 0.5723 0.192 Uiso 1 1 calc R U . . .
H25B H 0.4392 0.5177 0.5283 0.192 Uiso 1 1 calc R U . . .
H25C H 0.4404 0.5389 0.6108 0.192 Uiso 1 1 calc R U . . .
C26 C 0.6052(5) 0.6413(3) 0.4832(2) 0.0916(14) Uani 1 1 d . . . . .
H26A H 0.6351 0.7021 0.4745 0.137 Uiso 1 1 calc R U . . .
H26B H 0.5544 0.6211 0.4431 0.137 Uiso 1 1 calc R U . . .
H26C H 0.6780 0.6017 0.4893 0.137 Uiso 1 1 calc R U . . .
C27 C 0.3953(4) 0.6889(3) 0.5353(3) 0.1002(16) Uani 1 1 d . . . . .
H27A H 0.3431 0.6901 0.5779 0.150 Uiso 1 1 calc R U . . .
H27B H 0.3500 0.6572 0.4979 0.150 Uiso 1 1 calc R U . . .
H27C H 0.4131 0.7500 0.5201 0.150 Uiso 1 1 calc R U . . .
C28 C 0.6828(3) 0.91984(18) 0.69500(16) 0.0487(7) Uani 1 1 d . . . . .
C29 C 0.7465(5) 0.9719(2) 0.6329(2) 0.0814(12) Uani 1 1 d . . . . .
H29A H 0.8350 0.9532 0.6284 0.122 Uiso 1 1 calc R U . . .
H29B H 0.7430 1.0360 0.6424 0.122 Uiso 1 1 calc R U . . .
H29C H 0.7014 0.9590 0.5890 0.122 Uiso 1 1 calc R U . . .
C30 C 0.5434(4) 0.9527(2) 0.7061(2) 0.0696(10) Uani 1 1 d . . . . .
H30A H 0.4952 0.9441 0.6626 0.104 Uiso 1 1 calc R U . . .
H30B H 0.5439 1.0160 0.7185 0.104 Uiso 1 1 calc R U . . .
H30C H 0.5041 0.9184 0.7442 0.104 Uiso 1 1 calc R U . . .
C31 C 0.7578(4) 0.9425(2) 0.7638(2) 0.0691(10) Uani 1 1 d . . . . .
H31A H 0.7167 0.9140 0.8041 0.104 Uiso 1 1 calc R U . . .
H31B H 0.7588 1.0072 0.7707 0.104 Uiso 1 1 calc R U . . .
H31C H 0.8449 0.9206 0.7596 0.104 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C17 1.735(3) . ?
O1 C1 1.214(3) . ?
O2 C1 1.382(3) . ?
O2 N1 1.428(3) . ?
O3 C21 1.372(3) . ?
O3 H3 0.8200 . ?
N1 C3 1.393(3) . ?
N1 C11 1.494(4) . ?
C1 C2 1.427(4) . ?
C2 C3 1.350(4) . ?
C2 C10 1.497(4) . ?
C3 C4 1.466(4) . ?
C4 C5 1.380(4) . ?
C4 C9 1.391(4) . ?
C5 C6 1.374(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.370(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C18 1.516(4) . ?
C11 C12 1.521(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.382(4) . ?
C12 C17 1.394(4) . ?
C13 C14 1.386(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.361(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(4) . ?
C16 H16 0.9300 . ?
C18 C23 1.378(4) . ?
C18 C19 1.389(4) . ?
C19 C20 1.393(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.409(4) . ?
C20 C28 1.542(4) . ?
C21 C22 1.404(4) . ?
C22 C23 1.392(4) . ?
C22 C24 1.542(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.507(5) . ?
C24 C27 1.528(5) . ?
C24 C26 1.530(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C31 1.534(4) . ?
C28 C29 1.536(5) . ?
C28 C30 1.535(5) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 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
C1 O2 N1 107.6(2) . . ?
C21 O3 H3 109.5 . . ?
C3 N1 O2 106.38(19) . . ?
C3 N1 C11 119.8(2) . . ?
O2 N1 C11 108.67(19) . . ?
O1 C1 O2 119.3(3) . . ?
O1 C1 C2 132.8(3) . . ?
O2 C1 C2 107.9(2) . . ?
C3 C2 C1 107.6(2) . . ?
C3 C2 C10 130.8(3) . . ?
C1 C2 C10 121.5(3) . . ?
C2 C3 N1 110.4(2) . . ?
C2 C3 C4 131.3(2) . . ?
N1 C3 C4 118.1(2) . . ?
C5 C4 C9 118.5(3) . . ?
C5 C4 C3 120.4(3) . . ?
C9 C4 C3 121.1(3) . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C7 C6 C5 120.6(4) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.8(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C4 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C18 111.3(2) . . ?
N1 C11 C12 109.1(2) . . ?
C18 C11 C12 116.0(2) . . ?
N1 C11 H11 106.6 . . ?
C18 C11 H11 106.6 . . ?
C12 C11 H11 106.6 . . ?
C13 C12 C17 116.8(2) . . ?
C13 C12 C11 122.4(2) . . ?
C17 C12 C11 120.8(2) . . ?
C12 C13 C14 121.2(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C12 122.0(3) . . ?
C16 C17 Cl1 118.4(3) . . ?
C12 C17 Cl1 119.5(2) . . ?
C23 C18 C19 118.8(2) . . ?
C23 C18 C11 119.4(2) . . ?
C19 C18 C11 121.8(2) . . ?
C18 C19 C20 121.5(2) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C19 C20 C21 117.4(2) . . ?
C19 C20 C28 120.2(2) . . ?
C21 C20 C28 122.4(2) . . ?
O3 C21 C22 122.3(2) . . ?
O3 C21 C20 115.2(2) . . ?
C22 C21 C20 122.4(2) . . ?
C23 C22 C21 116.4(2) . . ?
C23 C22 C24 119.5(2) . . ?
C21 C22 C24 124.1(2) . . ?
C18 C23 C22 123.1(2) . . ?
C18 C23 H23 118.5 . . ?
C22 C23 H23 118.5 . . ?
C25 C24 C27 107.0(4) . . ?
C25 C24 C26 107.6(4) . . ?
C27 C24 C26 108.4(3) . . ?
C25 C24 C22 112.0(2) . . ?
C27 C24 C22 112.9(3) . . ?
C26 C24 C22 108.9(3) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C31 C28 C29 107.6(3) . . ?
C31 C28 C30 107.1(3) . . ?
C29 C28 C30 110.4(3) . . ?
C31 C28 C20 111.6(2) . . ?
C29 C28 C20 111.2(3) . . ?
C30 C28 C20 108.8(3) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
C1 O2 N1 C3 -3.0(3) . . . . ?
C1 O2 N1 C11 -133.3(2) . . . . ?
N1 O2 C1 O1 -176.6(3) . . . . ?
N1 O2 C1 C2 1.1(3) . . . . ?
O1 C1 C2 C3 178.5(4) . . . . ?
O2 C1 C2 C3 1.2(4) . . . . ?
O1 C1 C2 C10 2.1(7) . . . . ?
O2 C1 C2 C10 -175.2(4) . . . . ?
C1 C2 C3 N1 -3.2(4) . . . . ?
C10 C2 C3 N1 172.8(4) . . . . ?
C1 C2 C3 C4 -177.6(3) . . . . ?
C10 C2 C3 C4 -1.6(7) . . . . ?
O2 N1 C3 C2 3.8(3) . . . . ?
C11 N1 C3 C2 127.4(3) . . . . ?
O2 N1 C3 C4 179.1(2) . . . . ?
C11 N1 C3 C4 -57.3(3) . . . . ?
C2 C3 C4 C5 -43.6(5) . . . . ?
N1 C3 C4 C5 142.3(3) . . . . ?
C2 C3 C4 C9 136.5(4) . . . . ?
N1 C3 C4 C9 -37.6(4) . . . . ?
C9 C4 C5 C6 0.7(5) . . . . ?
C3 C4 C5 C6 -179.2(3) . . . . ?
C4 C5 C6 C7 0.0(6) . . . . ?
C5 C6 C7 C8 -1.1(6) . . . . ?
C6 C7 C8 C9 1.6(6) . . . . ?
C7 C8 C9 C4 -0.9(5) . . . . ?
C5 C4 C9 C8 -0.2(5) . . . . ?
C3 C4 C9 C8 179.7(3) . . . . ?
C3 N1 C11 C18 -74.9(3) . . . . ?
O2 N1 C11 C18 47.6(3) . . . . ?
C3 N1 C11 C12 155.8(2) . . . . ?
O2 N1 C11 C12 -81.7(2) . . . . ?
N1 C11 C12 C13 13.3(4) . . . . ?
C18 C11 C12 C13 -113.4(3) . . . . ?
N1 C11 C12 C17 -164.7(2) . . . . ?
C18 C11 C12 C17 68.6(3) . . . . ?
C17 C12 C13 C14 0.5(5) . . . . ?
C11 C12 C13 C14 -177.6(3) . . . . ?
C12 C13 C14 C15 -1.0(6) . . . . ?
C13 C14 C15 C16 0.3(6) . . . . ?
C14 C15 C16 C17 0.9(6) . . . . ?
C15 C16 C17 C12 -1.5(5) . . . . ?
C15 C16 C17 Cl1 177.6(3) . . . . ?
C13 C12 C17 C16 0.8(4) . . . . ?
C11 C12 C17 C16 178.9(3) . . . . ?
C13 C12 C17 Cl1 -178.3(2) . . . . ?
C11 C12 C17 Cl1 -0.2(4) . . . . ?
N1 C11 C18 C23 70.8(3) . . . . ?
C12 C11 C18 C23 -163.6(2) . . . . ?
N1 C11 C18 C19 -106.7(3) . . . . ?
C12 C11 C18 C19 18.9(4) . . . . ?
C23 C18 C19 C20 -1.1(4) . . . . ?
C11 C18 C19 C20 176.5(3) . . . . ?
C18 C19 C20 C21 -3.8(4) . . . . ?
C18 C19 C20 C28 174.9(3) . . . . ?
C19 C20 C21 O3 -176.0(3) . . . . ?
C28 C20 C21 O3 5.3(4) . . . . ?
C19 C20 C21 C22 7.1(4) . . . . ?
C28 C20 C21 C22 -171.6(3) . . . . ?
O3 C21 C22 C23 178.1(3) . . . . ?
C20 C21 C22 C23 -5.2(4) . . . . ?
O3 C21 C22 C24 0.4(4) . . . . ?
C20 C21 C22 C24 177.1(3) . . . . ?
C19 C18 C23 C22 3.1(4) . . . . ?
C11 C18 C23 C22 -174.6(3) . . . . ?
C21 C22 C23 C18 0.0(4) . . . . ?
C24 C22 C23 C18 177.8(3) . . . . ?
C23 C22 C24 C25 18.8(5) . . . . ?
C21 C22 C24 C25 -163.5(4) . . . . ?
C23 C22 C24 C27 139.7(3) . . . . ?
C21 C22 C24 C27 -42.7(4) . . . . ?
C23 C22 C24 C26 -100.0(3) . . . . ?
C21 C22 C24 C26 77.7(4) . . . . ?
C19 C20 C28 C31 -0.5(4) . . . . ?
C21 C20 C28 C31 178.1(3) . . . . ?
C19 C20 C28 C29 119.7(3) . . . . ?
C21 C20 C28 C29 -61.6(4) . . . . ?
C19 C20 C28 C30 -118.5(3) . . . . ?
C21 C20 C28 C30 60.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O1 0.82 2.20 2.914(3) 145.0 4_466

_refine_diff_density_max         0.147
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.028

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_chemical_compound_source        synthesis
_chemical_properties_physical    stable
_exptl_crystal_preparation       no
