# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_dd18229_0m
_database_code_depnum_ccdc_archive 'CCDC 1875350'
loop_
_audit_author_name
_audit_author_address

(R)-4-benzyl-4-((S)-(4-chlorophenyl)(2-hydroxy-3-methoxyphenyl)methyl)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2018-10-25 deposited with the CCDC.	2019-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
(R)-4-benzyl-4-((S)-(4-chlorophenyl)(2-hydroxy-3-methoxyphenyl)methyl)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
_chemical_name_common            
(R)-4-benzyl-4-((S)-(4-chlorophenyl)(2-hydroxy-3-methoxyphenyl)methyl)-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
_chemical_melting_point          ?
_chemical_formula_moiety         C31H27ClN2O3,H2O
_chemical_formula_sum            'C31 H29 Cl N2 O4'
_chemical_formula_weight         529.01

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                   9.0064(3)
_cell_length_b                   9.7885(3)
_cell_length_c                   30.9078(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2724.80(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5662
_cell_measurement_theta_min      5.235
_cell_measurement_theta_max      50.074

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             1112
_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    0.179
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6367
_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            13582
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.182
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             5302
_reflns_number_gt                4227
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.990

_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          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²+0.2398P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.030(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1487 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5302
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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 -0.33557(11) 0.77869(13) 0.45671(4) 0.0909(4) Uani 1 1 d . . . . .
O1 O 0.3418(3) 0.3073(2) 0.31386(7) 0.0624(6) Uani 1 1 d . . . . .
O2 O 0.0714(3) 0.6944(3) 0.29102(9) 0.0784(8) Uani 1 1 d . . . . .
H2 H 0.0352 0.7616 0.2792 0.118 Uiso 1 1 calc R U . . .
O3 O 0.2165(3) 0.9096(3) 0.25731(9) 0.0859(9) Uani 1 1 d . . . . .
N1 N 0.4893(3) 0.3262(3) 0.37493(9) 0.0505(6) Uani 1 1 d . . . . .
N2 N 0.4777(3) 0.3844(3) 0.41652(9) 0.0531(7) Uani 1 1 d . . . . .
C1 C 0.3628(3) 0.3452(3) 0.35097(11) 0.0485(7) Uani 1 1 d . . . . .
C2 C 0.2525(3) 0.4145(3) 0.38084(10) 0.0455(7) Uani 1 1 d . . . . .
C3 C 0.3500(4) 0.4408(3) 0.41966(10) 0.0510(7) Uani 1 1 d . . . . .
C4 C 0.3092(5) 0.5126(4) 0.46057(12) 0.0754(11) Uani 1 1 d . . . . .
H4A H 0.3737 0.4831 0.4835 0.113 Uiso 1 1 calc R U . . .
H4B H 0.2082 0.4914 0.4680 0.113 Uiso 1 1 calc R U . . .
H4C H 0.3193 0.6094 0.4566 0.113 Uiso 1 1 calc R U . . .
C5 C 0.1361(4) 0.3027(3) 0.39359(12) 0.0572(8) Uani 1 1 d . . . . .
H5A H 0.0580 0.3457 0.4104 0.069 Uiso 1 1 calc R U . . .
H5B H 0.0914 0.2672 0.3673 0.069 Uiso 1 1 calc R U . . .
C6 C 0.1977(3) 0.1846(3) 0.41925(12) 0.0552(8) Uani 1 1 d . . . . .
C7 C 0.1756(5) 0.1778(4) 0.46384(13) 0.0711(10) Uani 1 1 d . . . . .
H7 H 0.1172 0.2435 0.4774 0.085 Uiso 1 1 calc R U . . .
C8 C 0.2387(5) 0.0758(4) 0.48814(14) 0.0831(13) Uani 1 1 d . . . . .
H8 H 0.2221 0.0724 0.5178 0.100 Uiso 1 1 calc R U . . .
C9 C 0.3263(5) -0.0214(4) 0.46868(15) 0.0774(12) Uani 1 1 d . . . . .
H9 H 0.3718 -0.0888 0.4852 0.093 Uiso 1 1 calc R U . . .
C10 C 0.3464(4) -0.0185(3) 0.42477(14) 0.0689(10) Uani 1 1 d . . . . .
H10 H 0.4039 -0.0852 0.4115 0.083 Uiso 1 1 calc R U . . .
C11 C 0.2815(4) 0.0832(3) 0.40009(12) 0.0581(9) Uani 1 1 d . . . . .
H11 H 0.2945 0.0833 0.3702 0.070 Uiso 1 1 calc R U . . .
C12 C 0.6123(3) 0.2391(3) 0.36592(12) 0.0562(9) Uani 1 1 d . . . . .
C13 C 0.6919(4) 0.1854(4) 0.39989(14) 0.0727(11) Uani 1 1 d . . . . .
H13 H 0.6676 0.2080 0.4282 0.087 Uiso 1 1 calc R U . . .
C14 C 0.8088(5) 0.0973(5) 0.3914(2) 0.0936(15) Uani 1 1 d . . . . .
H14 H 0.8626 0.0600 0.4142 0.112 Uiso 1 1 calc R U . . .
C15 C 0.8453(5) 0.0649(5) 0.3498(2) 0.1028(17) Uani 1 1 d . . . . .
H15 H 0.9233 0.0050 0.3444 0.123 Uiso 1 1 calc R U . . .
C16 C 0.7674(5) 0.1204(6) 0.31613(19) 0.1009(16) Uani 1 1 d . . . . .
H16 H 0.7934 0.0990 0.2878 0.121 Uiso 1 1 calc R U . . .
C17 C 0.6502(4) 0.2081(4) 0.32395(14) 0.0784(11) Uani 1 1 d . . . . .
H17 H 0.5973 0.2458 0.3010 0.094 Uiso 1 1 calc R U . . .
C18 C 0.1726(3) 0.5336(3) 0.35656(10) 0.0450(7) Uani 1 1 d . . . . .
H18 H 0.1242 0.4899 0.3318 0.054 Uiso 1 1 calc R U . . .
C19 C 0.2729(3) 0.6425(3) 0.33684(10) 0.0470(7) Uani 1 1 d . . . . .
C20 C 0.4170(4) 0.6694(3) 0.34979(12) 0.0574(8) Uani 1 1 d . . . . .
H20 H 0.4601 0.6160 0.3713 0.069 Uiso 1 1 calc R U . . .
C21 C 0.4981(4) 0.7741(4) 0.33141(12) 0.0669(10) Uani 1 1 d . . . . .
H21 H 0.5959 0.7883 0.3400 0.080 Uiso 1 1 calc R U . . .
C22 C 0.4358(4) 0.8573(4) 0.30059(12) 0.0648(10) Uani 1 1 d . . . . .
H22 H 0.4900 0.9291 0.2888 0.078 Uiso 1 1 calc R U . . .
C23 C 0.2927(4) 0.8335(4) 0.28741(11) 0.0599(9) Uani 1 1 d . . . . .
C24 C 0.2121(4) 0.7245(4) 0.30482(10) 0.0554(8) Uani 1 1 d . . . . .
C25 C 0.2878(6) 1.0268(4) 0.23948(15) 0.0979(16) Uani 1 1 d . . . . .
H25A H 0.2188 1.0760 0.2217 0.147 Uiso 1 1 calc R U . . .
H25B H 0.3710 0.9984 0.2223 0.147 Uiso 1 1 calc R U . . .
H25C H 0.3217 1.0848 0.2625 0.147 Uiso 1 1 calc R U . . .
C26 C 0.0461(3) 0.5976(3) 0.38231(10) 0.0456(7) Uani 1 1 d . . . . .
C27 C 0.0680(3) 0.7113(3) 0.40822(11) 0.0541(8) Uani 1 1 d . . . . .
H27 H 0.1621 0.7501 0.4100 0.065 Uiso 1 1 calc R U . . .
C28 C -0.0477(4) 0.7677(3) 0.43138(11) 0.0586(9) Uani 1 1 d . . . . .
H28 H -0.0321 0.8432 0.4491 0.070 Uiso 1 1 calc R U . . .
C29 C -0.1875(4) 0.7100(4) 0.42780(11) 0.0596(9) Uani 1 1 d . . . . .
C30 C -0.2119(4) 0.5985(4) 0.40232(12) 0.0606(9) Uani 1 1 d . . . . .
H30 H -0.3060 0.5598 0.4006 0.073 Uiso 1 1 calc R U . . .
C31 C -0.0963(3) 0.5441(3) 0.37927(11) 0.0550(8) Uani 1 1 d . . . . .
H31 H -0.1135 0.4697 0.3612 0.066 Uiso 1 1 calc R U . . .
O4 O 0.8960(4) 0.8635(4) 0.24531(12) 0.1280(15) Uani 1 1 d . . . . .
H4D H 0.8062 0.8580 0.2290 0.192 Uiso 1 1 d R U . . .
H4E H 0.9122 0.9596 0.2341 0.192 Uiso 1 1 d 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 C29 1.741(3) . ?
O1 C1 1.220(4) . ?
O2 C24 1.369(4) . ?
O2 H2 0.8200 . ?
O3 C23 1.376(4) . ?
O3 C25 1.425(5) . ?
N1 C1 1.371(4) . ?
N1 N2 1.410(4) . ?
N1 C12 1.426(4) . ?
N2 C3 1.279(4) . ?
C1 C2 1.516(4) . ?
C2 C3 1.509(4) . ?
C2 C18 1.562(4) . ?
C2 C5 1.565(4) . ?
C3 C4 1.493(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.507(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.381(5) . ?
C6 C7 1.394(5) . ?
C7 C8 1.373(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.374(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.375(5) . ?
C12 C13 1.376(5) . ?
C13 C14 1.386(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C26 1.524(4) . ?
C18 C19 1.525(4) . ?
C18 H18 0.9800 . ?
C19 C20 1.384(4) . ?
C19 C24 1.387(4) . ?
C20 C21 1.380(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.374(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.371(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.399(5) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.385(4) . ?
C26 C31 1.389(4) . ?
C27 C28 1.380(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.384(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.364(5) . ?
C30 C31 1.369(5) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
O4 H4D 0.9552 . ?
O4 H4E 1.0125 . ?

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
C24 O2 H2 109.5 . . ?
C23 O3 C25 118.2(3) . . ?
C1 N1 N2 112.1(2) . . ?
C1 N1 C12 128.4(3) . . ?
N2 N1 C12 118.5(2) . . ?
C3 N2 N1 108.1(3) . . ?
O1 C1 N1 126.5(3) . . ?
O1 C1 C2 127.3(3) . . ?
N1 C1 C2 106.0(3) . . ?
C3 C2 C1 100.3(2) . . ?
C3 C2 C18 121.5(3) . . ?
C1 C2 C18 110.1(2) . . ?
C3 C2 C5 108.0(3) . . ?
C1 C2 C5 106.2(2) . . ?
C18 C2 C5 109.5(2) . . ?
N2 C3 C4 119.3(3) . . ?
N2 C3 C2 112.9(3) . . ?
C4 C3 C2 127.6(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C2 115.0(2) . . ?
C6 C5 H5A 108.5 . . ?
C2 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
C2 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C11 C6 C7 117.9(3) . . ?
C11 C6 C5 121.8(3) . . ?
C7 C6 C5 120.3(3) . . ?
C8 C7 C6 121.1(4) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 119.7(4) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.4(4) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C6 C11 C10 120.8(3) . . ?
C6 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C17 C12 C13 120.4(3) . . ?
C17 C12 N1 120.6(3) . . ?
C13 C12 N1 119.0(3) . . ?
C12 C13 C14 119.3(4) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 120.5(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.0(4) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 120.4(5) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 119.4(4) . . ?
C12 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C26 C18 C19 111.3(2) . . ?
C26 C18 C2 113.6(2) . . ?
C19 C18 C2 116.2(2) . . ?
C26 C18 H18 104.8 . . ?
C19 C18 H18 104.8 . . ?
C2 C18 H18 104.8 . . ?
C20 C19 C24 117.8(3) . . ?
C20 C19 C18 125.0(3) . . ?
C24 C19 C18 117.1(3) . . ?
C21 C20 C19 121.2(3) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 120.6(3) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 119.3(3) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 O3 125.3(3) . . ?
C22 C23 C24 120.2(3) . . ?
O3 C23 C24 114.5(3) . . ?
O2 C24 C19 117.6(3) . . ?
O2 C24 C23 121.7(3) . . ?
C19 C24 C23 120.7(3) . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C31 118.3(3) . . ?
C27 C26 C18 121.7(3) . . ?
C31 C26 C18 120.0(3) . . ?
C28 C27 C26 120.9(3) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C29 118.8(3) . . ?
C27 C28 H28 120.6 . . ?
C29 C28 H28 120.6 . . ?
C30 C29 C28 121.3(3) . . ?
C30 C29 Cl1 118.8(3) . . ?
C28 C29 Cl1 119.9(3) . . ?
C29 C30 C31 119.3(3) . . ?
C29 C30 H30 120.4 . . ?
C31 C30 H30 120.4 . . ?
C30 C31 C26 121.3(3) . . ?
C30 C31 H31 119.3 . . ?
C26 C31 H31 119.3 . . ?
H4D O4 H4E 89.7 . . ?

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 N1 N2 C3 -0.8(3) . . . . ?
C12 N1 N2 C3 -170.4(3) . . . . ?
N2 N1 C1 O1 179.2(3) . . . . ?
C12 N1 C1 O1 -12.6(5) . . . . ?
N2 N1 C1 C2 -4.2(3) . . . . ?
C12 N1 C1 C2 164.1(3) . . . . ?
O1 C1 C2 C3 -176.7(3) . . . . ?
N1 C1 C2 C3 6.7(3) . . . . ?
O1 C1 C2 C18 -47.5(4) . . . . ?
N1 C1 C2 C18 135.9(2) . . . . ?
O1 C1 C2 C5 71.0(4) . . . . ?
N1 C1 C2 C5 -105.6(3) . . . . ?
N1 N2 C3 C4 -179.1(3) . . . . ?
N1 N2 C3 C2 5.7(3) . . . . ?
C1 C2 C3 N2 -7.8(3) . . . . ?
C18 C2 C3 N2 -129.2(3) . . . . ?
C5 C2 C3 N2 103.1(3) . . . . ?
C1 C2 C3 C4 177.4(3) . . . . ?
C18 C2 C3 C4 56.0(5) . . . . ?
C5 C2 C3 C4 -71.6(4) . . . . ?
C3 C2 C5 C6 -42.9(4) . . . . ?
C1 C2 C5 C6 64.0(4) . . . . ?
C18 C2 C5 C6 -177.2(3) . . . . ?
C2 C5 C6 C11 -75.4(4) . . . . ?
C2 C5 C6 C7 102.2(4) . . . . ?
C11 C6 C7 C8 1.8(6) . . . . ?
C5 C6 C7 C8 -175.8(4) . . . . ?
C6 C7 C8 C9 0.5(7) . . . . ?
C7 C8 C9 C10 -2.1(7) . . . . ?
C8 C9 C10 C11 1.3(7) . . . . ?
C7 C6 C11 C10 -2.6(5) . . . . ?
C5 C6 C11 C10 175.0(3) . . . . ?
C9 C10 C11 C6 1.1(6) . . . . ?
C1 N1 C12 C17 29.0(5) . . . . ?
N2 N1 C12 C17 -163.4(3) . . . . ?
C1 N1 C12 C13 -150.3(3) . . . . ?
N2 N1 C12 C13 17.3(4) . . . . ?
C17 C12 C13 C14 -1.4(5) . . . . ?
N1 C12 C13 C14 178.0(3) . . . . ?
C12 C13 C14 C15 0.5(7) . . . . ?
C13 C14 C15 C16 0.6(8) . . . . ?
C14 C15 C16 C17 -0.8(8) . . . . ?
C13 C12 C17 C16 1.1(6) . . . . ?
N1 C12 C17 C16 -178.2(4) . . . . ?
C15 C16 C17 C12 0.0(7) . . . . ?
C3 C2 C18 C26 -70.6(3) . . . . ?
C1 C2 C18 C26 172.8(2) . . . . ?
C5 C2 C18 C26 56.4(3) . . . . ?
C3 C2 C18 C19 60.5(4) . . . . ?
C1 C2 C18 C19 -56.1(3) . . . . ?
C5 C2 C18 C19 -172.5(3) . . . . ?
C26 C18 C19 C20 110.2(3) . . . . ?
C2 C18 C19 C20 -22.0(4) . . . . ?
C26 C18 C19 C24 -66.8(4) . . . . ?
C2 C18 C19 C24 161.0(3) . . . . ?
C24 C19 C20 C21 -0.2(5) . . . . ?
C18 C19 C20 C21 -177.2(3) . . . . ?
C19 C20 C21 C22 2.1(6) . . . . ?
C20 C21 C22 C23 -1.6(6) . . . . ?
C21 C22 C23 O3 179.2(4) . . . . ?
C21 C22 C23 C24 -0.8(5) . . . . ?
C25 O3 C23 C22 -3.0(6) . . . . ?
C25 O3 C23 C24 177.0(4) . . . . ?
C20 C19 C24 O2 177.7(3) . . . . ?
C18 C19 C24 O2 -5.1(5) . . . . ?
C20 C19 C24 C23 -2.2(5) . . . . ?
C18 C19 C24 C23 175.1(3) . . . . ?
C22 C23 C24 O2 -177.2(3) . . . . ?
O3 C23 C24 O2 2.8(5) . . . . ?
C22 C23 C24 C19 2.7(5) . . . . ?
O3 C23 C24 C19 -177.3(3) . . . . ?
C19 C18 C26 C27 -40.1(4) . . . . ?
C2 C18 C26 C27 93.3(3) . . . . ?
C19 C18 C26 C31 138.3(3) . . . . ?
C2 C18 C26 C31 -88.3(3) . . . . ?
C31 C26 C27 C28 1.8(5) . . . . ?
C18 C26 C27 C28 -179.8(3) . . . . ?
C26 C27 C28 C29 -1.0(5) . . . . ?
C27 C28 C29 C30 0.7(5) . . . . ?
C27 C28 C29 Cl1 179.9(3) . . . . ?
C28 C29 C30 C31 -1.1(5) . . . . ?
Cl1 C29 C30 C31 179.7(3) . . . . ?
C29 C30 C31 C26 1.9(5) . . . . ?
C27 C26 C31 C30 -2.2(5) . . . . ?
C18 C26 C31 C30 179.3(3) . . . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.030

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane and ethyl acetate'
_chemical_properties_physical    Heat-sensitive
