# 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 
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data_cu_60408aa
_database_code_depnum_ccdc_archive 'CCDC 1812609'
_audit_update_record             
;
2017-12-20 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H28 N2 O8'
_chemical_formula_weight         436.45

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   11.4833(6)
_cell_length_b                   7.3773(5)
_cell_length_c                   13.1160(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.533(4)
_cell_angle_gamma                90
_cell_volume                     1103.92(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.849
_shelx_estimated_absorpt_T_min   0.588
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5125
_diffrn_reflns_av_unetI/netI     0.1527
_diffrn_reflns_av_R_equivalents  0.2527
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.874
_diffrn_reflns_theta_max         67.492
_diffrn_reflns_theta_full        67.492
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measured_fraction_theta_full 0.916
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_Laue_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.706
_diffrn_reflns_point_group_measured_fraction_full 0.706
_reflns_number_total             2812
_reflns_number_gt                2219
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.422
_reflns_Friedel_fraction_max     0.457
_reflns_Friedel_fraction_full    0.457

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.2000P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   1.7(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2812
_refine_ls_number_parameters     284
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1605
_refine_ls_R_factor_gt           0.1491
_refine_ls_wR_factor_ref         0.3552
_refine_ls_wR_factor_gt          0.3396
_refine_ls_goodness_of_fit_ref   1.408
_refine_ls_restrained_S_all      1.405
_refine_ls_shift/su_max          0.156
_refine_ls_shift/su_mean         0.027

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
N1 N 0.8909(7) 0.4112(12) -0.1436(4) 0.0289(18) Uani 1 1 d . . . . .
N2 N 0.3074(8) 0.6213(15) 0.6580(6) 0.038(2) Uani 1 1 d . . . . .
O1 O 1.0796(6) 0.3571(13) -0.1016(4) 0.0380(19) Uani 1 1 d . . . . .
O2 O 0.9622(7) 0.2688(12) 0.0117(5) 0.040(2) Uani 1 1 d . . . . .
O3 O 0.7214(5) 0.5163(10) -0.2213(4) 0.0304(16) Uani 1 1 d . . . . .
O4 O 0.6906(8) 0.0900(11) -0.1517(5) 0.044(2) Uani 1 1 d . . . . .
O5 O 0.6157(6) 0.5543(12) 0.2875(4) 0.0379(18) Uani 1 1 d . . . . .
O6 O 0.7439(7) 0.7084(13) 0.3970(5) 0.044(2) Uani 1 1 d . . . . .
O7 O 0.2087(7) 0.6790(15) 0.6302(5) 0.053(2) Uani 1 1 d . . . . .
O8 O 0.3384(7) 0.5660(15) 0.7446(5) 0.048(2) Uani 1 1 d . . . . .
C1 C 0.9739(9) 0.3412(15) -0.0722(6) 0.033(2) Uani 1 1 d . . . . .
C2 C 0.9436(8) 0.4636(16) -0.2367(5) 0.031(2) Uani 1 1 d . . . . .
H2 H 0.9181 0.5895 -0.2566 0.037 Uiso 1 1 calc R U . . .
C3 C 1.0731(9) 0.4667(17) -0.1955(6) 0.038(3) Uani 1 1 d . . . . .
H3A H 1.1215 0.4129 -0.2455 0.045 Uiso 1 1 calc R U . . .
H3B H 1.1001 0.5922 -0.1799 0.045 Uiso 1 1 calc R U . . .
C4 C 0.7675(7) 0.4385(12) -0.1464(5) 0.0211(18) Uani 1 1 d . . . . .
C5 C 0.6954(8) 0.3715(16) -0.0625(5) 0.030(2) Uani 1 1 d . . . . .
C6 C 0.7334(9) 0.4751(15) 0.0370(6) 0.032(2) Uani 1 1 d . . . . .
H6A H 0.8104 0.4273 0.0669 0.038 Uiso 1 1 calc R U . . .
H6B H 0.7446 0.6040 0.0196 0.038 Uiso 1 1 calc R U . . .
C7 C 0.6493(9) 0.4660(15) 0.1190(6) 0.032(2) Uani 1 1 d . . . . .
H7A H 0.5731 0.5206 0.0923 0.039 Uiso 1 1 calc R U . . .
H7B H 0.6355 0.3379 0.1366 0.039 Uiso 1 1 calc R U . . .
C8 C 0.7004(10) 0.5664(18) 0.2131(6) 0.040(3) Uani 1 1 d . . . . .
H8A H 0.7758 0.5111 0.2413 0.048 Uiso 1 1 calc R U . . .
H8B H 0.7145 0.6947 0.1963 0.048 Uiso 1 1 calc R U . . .
C9 C 0.6491(9) 0.6360(16) 0.3766(6) 0.033(2) Uani 1 1 d . . . . .
C10 C 0.5558(10) 0.6302(16) 0.4484(6) 0.035(2) Uani 1 1 d . . . . .
C11 C 0.4378(8) 0.6238(16) 0.4128(6) 0.032(2) Uani 1 1 d . . . . .
H11 H 0.4138 0.6201 0.3411 0.038 Uiso 1 1 calc R U . . .
C12 C 0.3554(9) 0.6226(19) 0.4804(7) 0.041(3) Uani 1 1 d . . . . .
H12 H 0.2742 0.6234 0.4562 0.050 Uiso 1 1 calc R U . . .
C13 C 0.3922(8) 0.6204(15) 0.5837(6) 0.030(2) Uani 1 1 d . . . . .
C14 C 0.5119(9) 0.6264(17) 0.6207(6) 0.035(2) Uani 1 1 d . . . . .
H14 H 0.5365 0.6248 0.6923 0.042 Uiso 1 1 calc R U . . .
C15 C 0.5914(9) 0.6345(17) 0.5521(7) 0.033(2) Uani 1 1 d . . . . .
H15 H 0.6725 0.6432 0.5759 0.040 Uiso 1 1 calc R U . . .
C16 C 0.9122(8) 0.3374(16) -0.3281(6) 0.034(2) Uani 1 1 d D . . . .
H16 H 0.8248 0.3333 -0.3416 0.040 Uiso 1 1 calc R U . . .
C17 C 0.9549(11) 0.1442(19) -0.3076(9) 0.053(3) Uani 1 1 d D U . . .
H17A H 0.9303 0.1018 -0.2425 0.079 Uiso 1 1 calc R U . . .
H17B H 1.0407 0.1410 -0.3035 0.079 Uiso 1 1 calc R U . . .
H17C H 0.9214 0.0652 -0.3634 0.079 Uiso 1 1 calc R U . . .
C18 C 0.9584(10) 0.418(2) -0.4239(6) 0.056(4) Uani 1 1 d . . . . .
H18A H 1.0414 0.4485 -0.4079 0.083 Uiso 1 1 calc R U . . .
H18B H 0.9137 0.5270 -0.4453 0.083 Uiso 1 1 calc R U . . .
H18C H 0.9494 0.3282 -0.4795 0.083 Uiso 1 1 calc R U . . .
C19 C 0.7097(8) 0.1647(14) -0.0519(6) 0.030(2) Uani 1 1 d . . . . .
H19A H 0.7895 0.1344 -0.0197 0.036 Uiso 1 1 calc R U . . .
H19B H 0.6521 0.1152 -0.0085 0.036 Uiso 1 1 calc R U . . .
C20 C 0.7075(14) -0.096(2) -0.1531(9) 0.059(4) Uani 1 1 d . . . . .
H20A H 0.6541 -0.1545 -0.1101 0.089 Uiso 1 1 calc R U . . .
H20B H 0.7887 -0.1237 -0.1264 0.089 Uiso 1 1 calc R U . . .
H20C H 0.6916 -0.1403 -0.2237 0.089 Uiso 1 1 calc R U . . .
C21 C 0.5665(8) 0.4084(16) -0.1013(6) 0.033(2) Uani 1 1 d . . . . .
H21A H 0.5501 0.3670 -0.1725 0.049 Uiso 1 1 calc R U . . .
H21B H 0.5509 0.5388 -0.0979 0.049 Uiso 1 1 calc R U . . .
H21C H 0.5160 0.3432 -0.0583 0.049 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
N1 C1 1.359(12) . ?
N1 C4 1.428(12) . ?
N1 C2 1.475(11) . ?
N2 O8 1.220(10) . ?
N2 O7 1.226(12) . ?
N2 C13 1.454(14) . ?
O1 C1 1.319(14) . ?
O1 C3 1.468(11) . ?
O2 C1 1.245(13) . ?
O3 C4 1.206(10) . ?
O4 C20 1.384(18) . ?
O4 C19 1.414(10) . ?
O5 C9 1.333(11) . ?
O5 C8 1.456(12) . ?
O6 C9 1.215(13) . ?
C2 C3 1.524(13) . ?
C2 C16 1.528(12) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.533(13) . ?
C5 C6 1.533(11) . ?
C5 C21 1.534(12) . ?
C5 C19 1.539(16) . ?
C6 C7 1.526(14) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.501(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.505(16) . ?
C10 C15 1.376(12) . ?
C10 C11 1.383(15) . ?
C11 C12 1.368(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.373(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.404(13) . ?
C14 C15 1.354(16) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.522(15) . ?
C16 C18 1.536(15) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C1 N1 C4 133.5(7) . . ?
C1 N1 C2 110.4(8) . . ?
C4 N1 C2 116.2(6) . . ?
O8 N2 O7 123.7(9) . . ?
O8 N2 C13 118.4(8) . . ?
O7 N2 C13 117.9(7) . . ?
C1 O1 C3 109.5(7) . . ?
C20 O4 C19 113.0(8) . . ?
C9 O5 C8 114.3(8) . . ?
O2 C1 O1 119.4(9) . . ?
O2 C1 N1 129.4(10) . . ?
O1 C1 N1 111.2(8) . . ?
N1 C2 C3 100.7(6) . . ?
N1 C2 C16 114.1(9) . . ?
C3 C2 C16 114.9(9) . . ?
N1 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
C16 C2 H2 108.9 . . ?
O1 C3 C2 104.1(8) . . ?
O1 C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
O1 C3 H3B 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 109.0 . . ?
O3 C4 N1 115.5(8) . . ?
O3 C4 C5 121.0(8) . . ?
N1 C4 C5 123.5(6) . . ?
C4 C5 C6 109.0(9) . . ?
C4 C5 C21 106.5(6) . . ?
C6 C5 C21 111.4(8) . . ?
C4 C5 C19 108.9(8) . . ?
C6 C5 C19 113.6(7) . . ?
C21 C5 C19 107.2(9) . . ?
C7 C6 C5 115.9(8) . . ?
C7 C6 H6A 108.4 . . ?
C5 C6 H6A 108.3 . . ?
C7 C6 H6B 108.3 . . ?
C5 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C8 C7 C6 109.8(8) . . ?
C8 C7 H7A 109.8 . . ?
C6 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.2 . . ?
O5 C8 C7 107.0(8) . . ?
O5 C8 H8A 110.3 . . ?
C7 C8 H8A 110.4 . . ?
O5 C8 H8B 110.3 . . ?
C7 C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
O6 C9 O5 123.6(9) . . ?
O6 C9 C10 124.0(8) . . ?
O5 C9 C10 112.4(8) . . ?
C15 C10 C11 120.2(10) . . ?
C15 C10 C9 117.8(9) . . ?
C11 C10 C9 122.0(7) . . ?
C12 C11 C10 120.3(7) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 118.8(9) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C12 C13 C14 121.3(10) . . ?
C12 C13 N2 120.5(9) . . ?
C14 C13 N2 118.2(7) . . ?
C15 C14 C13 118.7(7) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C10 120.6(9) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C17 C16 C2 112.9(7) . . ?
C17 C16 C18 111.8(10) . . ?
C2 C16 C18 109.6(10) . . ?
C17 C16 H16 107.5 . . ?
C2 C16 H16 107.4 . . ?
C18 C16 H16 107.4 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.4 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.4 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 C5 107.4(7) . . ?
O4 C19 H19A 110.2 . . ?
C5 C19 H19A 110.3 . . ?
O4 C19 H19B 110.2 . . ?
C5 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.4 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.4 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C5 C21 H21A 109.5 . . ?
C5 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C5 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C3 O1 C1 O2 -172.7(10) . . . . ?
C3 O1 C1 N1 7.3(11) . . . . ?
C4 N1 C1 O2 4.9(19) . . . . ?
C2 N1 C1 O2 -173.3(10) . . . . ?
C4 N1 C1 O1 -175.1(9) . . . . ?
C2 N1 C1 O1 6.6(12) . . . . ?
C1 N1 C2 C3 -16.6(12) . . . . ?
C4 N1 C2 C3 164.8(8) . . . . ?
C1 N1 C2 C16 107.1(9) . . . . ?
C4 N1 C2 C16 -71.5(11) . . . . ?
C1 O1 C3 C2 -17.5(10) . . . . ?
N1 C2 C3 O1 19.6(10) . . . . ?
C16 C2 C3 O1 -103.5(10) . . . . ?
C1 N1 C4 O3 175.5(10) . . . . ?
C2 N1 C4 O3 -6.3(12) . . . . ?
C1 N1 C4 C5 -5.8(16) . . . . ?
C2 N1 C4 C5 172.4(9) . . . . ?
O3 C4 C5 C6 -115.1(9) . . . . ?
N1 C4 C5 C6 66.2(11) . . . . ?
O3 C4 C5 C21 5.2(13) . . . . ?
N1 C4 C5 C21 -173.5(8) . . . . ?
O3 C4 C5 C19 120.5(8) . . . . ?
N1 C4 C5 C19 -58.2(10) . . . . ?
C4 C5 C6 C7 163.3(8) . . . . ?
C21 C5 C6 C7 46.0(12) . . . . ?
C19 C5 C6 C7 -75.1(11) . . . . ?
C5 C6 C7 C8 177.6(9) . . . . ?
C9 O5 C8 C7 179.3(9) . . . . ?
C6 C7 C8 O5 179.4(8) . . . . ?
C8 O5 C9 O6 -2.9(16) . . . . ?
C8 O5 C9 C10 176.4(9) . . . . ?
O6 C9 C10 C15 -28.4(18) . . . . ?
O5 C9 C10 C15 152.3(10) . . . . ?
O6 C9 C10 C11 150.5(12) . . . . ?
O5 C9 C10 C11 -28.8(15) . . . . ?
C15 C10 C11 C12 0.4(17) . . . . ?
C9 C10 C11 C12 -178.6(12) . . . . ?
C10 C11 C12 C13 -2.6(18) . . . . ?
C11 C12 C13 C14 2.5(19) . . . . ?
C11 C12 C13 N2 179.3(10) . . . . ?
O8 N2 C13 C12 158.5(12) . . . . ?
O7 N2 C13 C12 -22.0(17) . . . . ?
O8 N2 C13 C14 -24.6(16) . . . . ?
O7 N2 C13 C14 154.9(11) . . . . ?
C12 C13 C14 C15 0.0(17) . . . . ?
N2 C13 C14 C15 -176.9(11) . . . . ?
C13 C14 C15 C10 -2.4(17) . . . . ?
C11 C10 C15 C14 2.2(18) . . . . ?
C9 C10 C15 C14 -178.8(11) . . . . ?
N1 C2 C16 C17 -61.9(12) . . . . ?
C3 C2 C16 C17 53.7(12) . . . . ?
N1 C2 C16 C18 172.8(9) . . . . ?
C3 C2 C16 C18 -71.5(11) . . . . ?
C20 O4 C19 C5 176.6(10) . . . . ?
C4 C5 C19 O4 -48.6(9) . . . . ?
C6 C5 C19 O4 -170.3(8) . . . . ?
C21 C5 C19 O4 66.2(10) . . . . ?

_refine_diff_density_max         0.777
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.203



####################################################################### 
# 
# 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_cu_20180907MQN_15_86_0m
_database_code_depnum_ccdc_archive 'CCDC 1868095'
_audit_update_record             
;
2018-09-17 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H34 Br0 Cl N O4'
_chemical_formula_weight         532.05

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'
N N 0.0311 0.0180 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.1903(12)
_cell_length_b                   13.744(3)
_cell_length_c                   32.103(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2731.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.542
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17920
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         3.498
_diffrn_reflns_theta_max         70.409
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             5047
_reflns_number_gt                4857
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_max     0.939
_reflns_Friedel_fraction_full    0.954

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0453P)²+0.4600P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1954 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.046(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5047
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.004

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
O1 O 0.7811(3) 0.31061(12) 0.46061(5) 0.0266(4) Uani 1 1 d . . . . .
C1 C 0.6104(6) 0.6441(2) 0.51254(9) 0.0406(7) Uani 1 1 d . . . . .
H1 H 0.552440 0.705779 0.516769 0.049 Uiso 1 1 calc R U . . .
O2 O 0.8608(3) 0.15714(11) 0.29916(5) 0.0276(4) Uani 1 1 d . . . . .
C2 C 0.8055(6) 0.6192(2) 0.53040(9) 0.0400(7) Uani 1 1 d . . . . .
H2 H 0.878910 0.664288 0.546702 0.048 Uiso 1 1 calc R U . . .
C14 C 0.9378(5) 0.08260(19) 0.27256(9) 0.0384(7) Uani 1 1 d . . . . .
H14A H 1.084149 0.096480 0.264656 0.058 Uiso 1 1 calc R U . . .
H14B H 0.848955 0.079435 0.248085 0.058 Uiso 1 1 calc R U . . .
H14C H 0.932480 0.021367 0.286907 0.058 Uiso 1 1 calc R U . . .
O3 O 0.4949(3) 0.23130(12) 0.23312(5) 0.0257(4) Uani 1 1 d . . . . .
C3 C 0.8927(5) 0.52787(19) 0.52430(8) 0.0326(6) Uani 1 1 d . . . . .
H3 H 1.024107 0.511959 0.536586 0.039 Uiso 1 1 calc R U . . .
C15 C 0.4764(4) 0.29829(15) 0.31297(7) 0.0188(4) Uani 1 1 d . . . . .
H15 H 0.353252 0.272075 0.297417 0.023 Uiso 1 1 calc R U . . .
N5 N 0.6322(3) 0.33458(12) 0.28182(6) 0.0183(4) Uani 1 1 d . . . . .
C4 C 0.7853(4) 0.45915(17) 0.49984(7) 0.0262(5) Uani 1 1 d . . . . .
O4 O 0.2206(3) 0.37896(10) 0.36160(5) 0.0211(3) Uani 1 1 d . . . . .
C5 C 0.5887(4) 0.48450(19) 0.48194(8) 0.0310(5) Uani 1 1 d . . . . .
H5 H 0.514760 0.439602 0.465616 0.037 Uiso 1 1 calc R U . . .
C16 C 0.3969(4) 0.38714(15) 0.33530(7) 0.0189(4) Uani 1 1 d . . . . .
C6 C 0.5018(5) 0.5769(2) 0.48833(9) 0.0386(6) Uani 1 1 d . . . . .
H6 H 0.370258 0.593322 0.476246 0.046 Uiso 1 1 calc R U . . .
Cl6 Cl 1.23082(11) 0.39998(4) 0.10377(2) 0.03473(17) Uani 1 1 d . . . . .
C13 C 0.6575(4) 0.13162(15) 0.31623(7) 0.0227(5) Uani 1 1 d . . . . .
H13A H 0.674387 0.074436 0.333635 0.027 Uiso 1 1 calc R U . . .
H13B H 0.559150 0.115180 0.293784 0.027 Uiso 1 1 calc R U . . .
C7 C 0.8898(4) 0.36177(18) 0.49259(8) 0.0295(5) Uani 1 1 d . . . . .
H7A H 1.039880 0.371037 0.484846 0.035 Uiso 1 1 calc R U . . .
H7B H 0.885894 0.323997 0.518104 0.035 Uiso 1 1 calc R U . . .
C18 C 0.6577(4) 0.50627(15) 0.30513(7) 0.0246(5) Uani 1 1 d . . . . .
H18A H 0.752306 0.550612 0.319953 0.029 Uiso 1 1 calc R U . . .
H18B H 0.607451 0.538401 0.280032 0.029 Uiso 1 1 calc R U . . .
C29 C 0.8505(4) 0.41222(16) 0.14522(7) 0.0257(5) Uani 1 1 d . . . . .
H29 H 0.803849 0.451828 0.123526 0.031 Uiso 1 1 calc R U . . .
C26 C 0.6243(4) 0.29544(15) 0.24300(7) 0.0200(4) Uani 1 1 d . . . . .
C17 C 0.4688(4) 0.47932(15) 0.33212(7) 0.0217(4) Uani 1 1 d . . . . .
C8 C 0.9074(4) 0.23237(17) 0.44444(7) 0.0263(5) Uani 1 1 d . . . . .
H8A H 0.940598 0.186350 0.466430 0.032 Uiso 1 1 calc R U . . .
H8B H 1.042250 0.257067 0.433248 0.032 Uiso 1 1 calc R U . . .
C12 C 0.5594(4) 0.21417(14) 0.34225(7) 0.0196(5) Uani 1 1 d . . . . .
C11 C 0.7187(4) 0.25292(14) 0.37509(6) 0.0207(4) Uani 1 1 d . . . . .
H11A H 0.850591 0.272081 0.360966 0.025 Uiso 1 1 calc R U . . .
H11B H 0.657129 0.311025 0.387456 0.025 Uiso 1 1 calc R U . . .
C22 C 0.0017(4) 0.59723(18) 0.41201(7) 0.0294(5) Uani 1 1 d . . . . .
H22 H -0.107061 0.618980 0.429690 0.035 Uiso 1 1 calc R U . . .
C31 C 1.1309(4) 0.31625(16) 0.17734(8) 0.0256(5) Uani 1 1 d . . . . .
H31 H 1.270511 0.291233 0.176824 0.031 Uiso 1 1 calc R U . . .
C21 C 0.0135(4) 0.49850(17) 0.40195(7) 0.0258(5) Uani 1 1 d . . . . .
H21 H -0.084439 0.453293 0.412344 0.031 Uiso 1 1 calc R U . . .
C32 C 0.9934(4) 0.29519(17) 0.21022(8) 0.0253(5) Uani 1 1 d . . . . .
H32 H 1.042450 0.257090 0.232217 0.030 Uiso 1 1 calc R U . . .
C9 C 0.7783(4) 0.18249(15) 0.41025(7) 0.0251(5) Uani 1 1 d . . . . .
H9A H 0.647262 0.155456 0.422087 0.030 Uiso 1 1 calc R U . . .
H9B H 0.862535 0.129213 0.398886 0.030 Uiso 1 1 calc R U . . .
C20 C 0.1800(4) 0.47230(15) 0.37559(7) 0.0207(4) Uani 1 1 d . . . . .
C19 C 0.7800(4) 0.41348(14) 0.29383(7) 0.0199(4) Uani 1 1 d . . . . .
H19A H 0.877750 0.426934 0.270932 0.024 Uiso 1 1 calc R U . . .
H19B H 0.865807 0.392803 0.317511 0.024 Uiso 1 1 calc R U . . .
C28 C 0.7132(4) 0.38958(15) 0.17800(7) 0.0235(5) Uani 1 1 d . . . . .
H28 H 0.573178 0.414109 0.178176 0.028 Uiso 1 1 calc R U . . .
C27 C 0.7826(4) 0.33056(14) 0.21063(7) 0.0213(4) Uani 1 1 d . . . . .
C10 C 0.3570(4) 0.17018(16) 0.36315(8) 0.0261(5) Uani 1 1 d . . . . .
H10A H 0.395074 0.110340 0.376713 0.039 Uiso 1 1 calc R U . . .
H10B H 0.248915 0.157734 0.342383 0.039 Uiso 1 1 calc R U . . .
H10C H 0.301231 0.215136 0.383357 0.039 Uiso 1 1 calc R U . . .
C25 C 0.3292(4) 0.53718(15) 0.35832(7) 0.0224(5) Uani 1 1 d . . . . .
C24 C 0.3136(5) 0.63600(16) 0.36919(8) 0.0286(5) Uani 1 1 d . . . . .
H24 H 0.410441 0.681464 0.358642 0.034 Uiso 1 1 calc R U . . .
C30 C 1.0578(4) 0.37487(16) 0.14538(7) 0.0237(5) Uani 1 1 d . . . . .
C23 C 0.1500(5) 0.66365(16) 0.39604(8) 0.0300(5) Uani 1 1 d . . . . .
H23 H 0.138604 0.728730 0.403665 0.036 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
O1 C7 1.415(3) . ?
O1 C8 1.427(3) . ?
C1 C6 1.382(5) . ?
C1 C2 1.380(5) . ?
C1 H1 0.9300 . ?
O2 C14 1.416(3) . ?
O2 C13 1.416(3) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O3 C26 1.232(3) . ?
C3 C4 1.397(4) . ?
C3 H3 0.9300 . ?
C15 N5 1.476(3) . ?
C15 C16 1.499(3) . ?
C15 C12 1.576(3) . ?
C15 H15 0.9800 . ?
N5 C26 1.359(3) . ?
N5 C19 1.470(3) . ?
C4 C5 1.390(4) . ?
C4 C7 1.505(4) . ?
O4 C20 1.382(3) . ?
O4 C16 1.384(3) . ?
C5 C6 1.394(4) . ?
C5 H5 0.9300 . ?
C16 C17 1.347(3) . ?
C6 H6 0.9300 . ?
Cl6 C30 1.747(2) . ?
C13 C12 1.535(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C18 C17 1.502(3) . ?
C18 C19 1.527(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C29 C30 1.382(4) . ?
C29 C28 1.388(3) . ?
C29 H29 0.9300 . ?
C26 C27 1.508(3) . ?
C17 C25 1.445(3) . ?
C8 C9 1.521(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 C10 1.544(3) . ?
C12 C11 1.539(3) . ?
C11 C9 1.532(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C22 C23 1.392(4) . ?
C22 C21 1.397(3) . ?
C22 H22 0.9300 . ?
C31 C32 1.386(4) . ?
C31 C30 1.381(3) . ?
C31 H31 0.9300 . ?
C21 C20 1.381(3) . ?
C21 H21 0.9300 . ?
C32 C27 1.393(4) . ?
C32 H32 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C20 C25 1.399(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C28 C27 1.393(3) . ?
C28 H28 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C25 C24 1.406(3) . ?
C24 C23 1.383(4) . ?
C24 H24 0.9300 . ?
C23 H23 0.9300 . ?

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 O1 C8 112.19(19) . . ?
C6 C1 C2 119.5(3) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C14 O2 C13 110.7(2) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
N5 C15 C16 105.26(17) . . ?
N5 C15 C12 116.05(18) . . ?
C16 C15 C12 114.79(18) . . ?
N5 C15 H15 106.7 . . ?
C16 C15 H15 106.7 . . ?
C12 C15 H15 106.7 . . ?
C26 N5 C19 123.71(18) . . ?
C26 N5 C15 117.67(18) . . ?
C19 N5 C15 118.57(17) . . ?
C5 C4 C3 118.7(2) . . ?
C5 C4 C7 122.4(2) . . ?
C3 C4 C7 118.9(2) . . ?
C20 O4 C16 105.44(16) . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C17 C16 O4 112.53(19) . . ?
C17 C16 C15 128.4(2) . . ?
O4 C16 C15 118.97(18) . . ?
C1 C6 C5 120.3(3) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
O2 C13 C12 112.28(17) . . ?
O2 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
O2 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
O1 C7 C4 110.5(2) . . ?
O1 C7 H7A 109.6 . . ?
C4 C7 H7A 109.6 . . ?
O1 C7 H7B 109.6 . . ?
C4 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C17 C18 C19 108.49(17) . . ?
C17 C18 H18A 110.0 . . ?
C19 C18 H18A 110.0 . . ?
C17 C18 H18B 110.0 . . ?
C19 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
C30 C29 C28 118.9(2) . . ?
C30 C29 H29 120.6 . . ?
C28 C29 H29 120.6 . . ?
O3 C26 N5 122.9(2) . . ?
O3 C26 C27 118.30(19) . . ?
N5 C26 C27 118.84(19) . . ?
C16 C17 C25 106.0(2) . . ?
C16 C17 C18 122.2(2) . . ?
C25 C17 C18 131.8(2) . . ?
O1 C8 C9 108.31(19) . . ?
O1 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
O1 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
C13 C12 C10 105.56(17) . . ?
C13 C12 C11 112.03(19) . . ?
C10 C12 C11 110.97(19) . . ?
C13 C12 C15 110.28(18) . . ?
C10 C12 C15 106.39(18) . . ?
C11 C12 C15 111.32(17) . . ?
C9 C11 C12 116.13(17) . . ?
C9 C11 H11A 108.3 . . ?
C12 C11 H11A 108.3 . . ?
C9 C11 H11B 108.3 . . ?
C12 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C23 C22 C21 121.2(2) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C32 C31 C30 119.1(2) . . ?
C32 C31 H31 120.5 . . ?
C30 C31 H31 120.5 . . ?
C20 C21 C22 115.7(2) . . ?
C20 C21 H21 122.1 . . ?
C22 C21 H21 122.1 . . ?
C31 C32 C27 120.6(2) . . ?
C31 C32 H32 119.7 . . ?
C27 C32 H32 119.7 . . ?
C8 C9 C11 111.92(18) . . ?
C8 C9 H9A 109.2 . . ?
C11 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C11 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
O4 C20 C21 125.2(2) . . ?
O4 C20 C25 110.06(19) . . ?
C21 C20 C25 124.7(2) . . ?
N5 C19 C18 111.71(19) . . ?
N5 C19 H19A 109.3 . . ?
C18 C19 H19A 109.3 . . ?
N5 C19 H19B 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C29 C28 C27 120.8(2) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C28 C27 C32 119.0(2) . . ?
C28 C27 C26 120.3(2) . . ?
C32 C27 C26 120.25(19) . . ?
C12 C10 H10A 109.5 . . ?
C12 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C12 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C20 C25 C24 118.2(2) . . ?
C20 C25 C17 105.95(19) . . ?
C24 C25 C17 135.9(2) . . ?
C23 C24 C25 118.1(2) . . ?
C23 C24 H24 121.0 . . ?
C25 C24 H24 121.0 . . ?
C29 C30 C31 121.6(2) . . ?
C29 C30 Cl6 119.55(18) . . ?
C31 C30 Cl6 118.86(19) . . ?
C22 C23 C24 122.1(2) . . ?
C22 C23 H23 118.9 . . ?
C24 C23 H23 118.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.0(5) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C16 C15 N5 C26 -137.23(19) . . . . ?
C12 C15 N5 C26 94.7(2) . . . . ?
C16 C15 N5 C19 40.1(2) . . . . ?
C12 C15 N5 C19 -88.0(2) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C2 C3 C4 C7 177.7(2) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C7 C4 C5 C6 -177.7(2) . . . . ?
C20 O4 C16 C17 0.2(2) . . . . ?
C20 O4 C16 C15 -176.99(19) . . . . ?
N5 C15 C16 C17 -7.8(3) . . . . ?
C12 C15 C16 C17 121.1(3) . . . . ?
N5 C15 C16 O4 168.88(18) . . . . ?
C12 C15 C16 O4 -62.3(3) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C14 O2 C13 C12 -175.1(2) . . . . ?
C8 O1 C7 C4 163.1(2) . . . . ?
C5 C4 C7 O1 10.0(3) . . . . ?
C3 C4 C7 O1 -167.8(2) . . . . ?
C19 N5 C26 O3 -177.8(2) . . . . ?
C15 N5 C26 O3 -0.6(3) . . . . ?
C19 N5 C26 C27 3.2(3) . . . . ?
C15 N5 C26 C27 -179.53(18) . . . . ?
O4 C16 C17 C25 -0.1(3) . . . . ?
C15 C16 C17 C25 176.8(2) . . . . ?
O4 C16 C17 C18 -179.6(2) . . . . ?
C15 C16 C17 C18 -2.7(4) . . . . ?
C19 C18 C17 C16 -15.6(3) . . . . ?
C19 C18 C17 C25 165.1(2) . . . . ?
C7 O1 C8 C9 -179.63(19) . . . . ?
O2 C13 C12 C10 -172.53(18) . . . . ?
O2 C13 C12 C11 -51.6(2) . . . . ?
O2 C13 C12 C15 72.9(2) . . . . ?
N5 C15 C12 C13 -51.0(2) . . . . ?
C16 C15 C12 C13 -174.30(19) . . . . ?
N5 C15 C12 C10 -165.04(18) . . . . ?
C16 C15 C12 C10 71.7(2) . . . . ?
N5 C15 C12 C11 73.9(2) . . . . ?
C16 C15 C12 C11 -49.3(3) . . . . ?
C13 C12 C11 C9 -66.9(3) . . . . ?
C10 C12 C11 C9 50.8(3) . . . . ?
C15 C12 C11 C9 169.09(19) . . . . ?
C23 C22 C21 C20 0.1(4) . . . . ?
C30 C31 C32 C27 1.6(3) . . . . ?
O1 C8 C9 C11 58.7(3) . . . . ?
C12 C11 C9 C8 -171.0(2) . . . . ?
C16 O4 C20 C21 178.4(2) . . . . ?
C16 O4 C20 C25 -0.2(2) . . . . ?
C22 C21 C20 O4 -179.8(2) . . . . ?
C22 C21 C20 C25 -1.4(4) . . . . ?
C26 N5 C19 C18 114.9(2) . . . . ?
C15 N5 C19 C18 -62.3(2) . . . . ?
C17 C18 C19 N5 44.1(2) . . . . ?
C30 C29 C28 C27 0.2(3) . . . . ?
C29 C28 C27 C32 0.7(3) . . . . ?
C29 C28 C27 C26 -171.8(2) . . . . ?
C31 C32 C27 C28 -1.6(3) . . . . ?
C31 C32 C27 C26 170.9(2) . . . . ?
O3 C26 C27 C28 73.5(3) . . . . ?
N5 C26 C27 C28 -107.5(2) . . . . ?
O3 C26 C27 C32 -98.9(3) . . . . ?
N5 C26 C27 C32 80.1(3) . . . . ?
O4 C20 C25 C24 -179.7(2) . . . . ?
C21 C20 C25 C24 1.7(4) . . . . ?
O4 C20 C25 C17 0.1(3) . . . . ?
C21 C20 C25 C17 -178.4(2) . . . . ?
C16 C17 C25 C20 0.0(3) . . . . ?
C18 C17 C25 C20 179.4(2) . . . . ?
C16 C17 C25 C24 179.8(3) . . . . ?
C18 C17 C25 C24 -0.7(5) . . . . ?
C20 C25 C24 C23 -0.6(4) . . . . ?
C17 C25 C24 C23 179.5(3) . . . . ?
C28 C29 C30 C31 -0.3(3) . . . . ?
C28 C29 C30 Cl6 178.39(18) . . . . ?
C32 C31 C30 C29 -0.6(3) . . . . ?
C32 C31 C30 Cl6 -179.29(18) . . . . ?
C21 C22 C23 C24 0.8(4) . . . . ?
C25 C24 C23 C22 -0.5(4) . . . . ?

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.054



