# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2182515'
loop_
_audit_author_name
_audit_author_address
'Yasunori Toda'
;Shinshu University
Japan
;
_audit_update_record             
;
2022-06-28 deposited with the CCDC.	2022-09-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H32 Br O P'
_chemical_formula_iupac          ?
_chemical_formula_weight         519.44

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.5046(12)
_cell_length_b                   10.4709(13)
_cell_length_c                   27.185(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.971(2)
_cell_angle_gamma                90
_cell_volume                     2690.8(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    189
_cell_measurement_theta_min      2.0895
_cell_measurement_theta_max      24.7086
_cell_measurement_temperature    93.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.240
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080

_exptl_absorpt_coefficient_mu    1.607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  0.70

_exptl_special_details           
;
;

_diffrn_ambient_temperature      93.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            30803
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_full        27.92
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             6403
_reflns_number_gt                4308
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1160
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_restrained_S_all      1.178
_refine_ls_number_reflns         6403
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0523P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.361
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2010.11.0.0'
_computing_cell_refinement       'APEX2 v2010.11-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.32165(3) 0.07280(3) 0.412154(10) 0.06376(13) Uani d . 1 . .
P P1 0.12545(6) 0.52776(6) 0.61136(2) 0.03114(14) Uani d . 1 . .
O O1 0.3245(2) 0.62140(18) 0.82142(6) 0.0517(5) Uani d . 1 . .
H H33 0.3047 0.5596 0.8392 0.078 Uiso calc R 1 . .
C C1 0.3692(3) 0.1920(3) 0.55533(11) 0.0570(8) Uani d . 1 . .
H H1 0.419 0.1214 0.5436 0.068 Uiso calc R 1 . .
C C2 0.3546(3) 0.2024(3) 0.60501(11) 0.0557(7) Uani d . 1 . .
H H2 0.3934 0.1387 0.6273 0.067 Uiso calc R 1 . .
C C3 0.2835(3) 0.3054(2) 0.62248(9) 0.0453(6) Uani d . 1 . .
H H3 0.2742 0.3131 0.6568 0.054 Uiso calc R 1 . .
C C4 0.2257(2) 0.3973(2) 0.58969(8) 0.0365(5) Uani d . 1 . .
C C5 0.1798(2) 0.55982(19) 0.67504(8) 0.0303(5) Uani d . 1 . .
C C6 0.2973(2) 0.6372(2) 0.68865(8) 0.0322(5) Uani d . 1 . .
H H6 0.3452 0.6764 0.6636 0.039 Uiso calc R 1 . .
C C7 0.3449(2) 0.6577(2) 0.73754(8) 0.0330(5) Uani d . 1 . .
C C8 0.4711(3) 0.7423(3) 0.75357(9) 0.0488(7) Uani d . 1 . .
H H8 0.5168 0.7037 0.7849 0.059 Uiso calc R 1 . .
C C9 0.5827(3) 0.7441(3) 0.71890(14) 0.0852(11) Uani d . 1 . .
H H9A 0.5466 0.7878 0.6883 0.128 Uiso calc R 1 . .
H H9B 0.6089 0.6563 0.7113 0.128 Uiso calc R 1 . .
H H9C 0.6661 0.7895 0.7343 0.128 Uiso calc R 1 . .
C C10 -0.0169(4) 0.3529(3) 0.78665(13) 0.0799(10) Uani d . 1 . .
H H10A -0.0596 0.3193 0.8153 0.12 Uiso calc R 1 . .
H H10B 0.0475 0.2891 0.7751 0.12 Uiso calc R 1 . .
H H10C -0.0914 0.3724 0.76 0.12 Uiso calc R 1 . .
C C11 0.0648(3) 0.4734(3) 0.80139(9) 0.0498(7) Uani d . 1 . .
H H11 0.1341 0.4506 0.8303 0.06 Uiso calc R 1 . .
C C12 -0.0284(5) 0.5756(4) 0.81878(17) 0.1146(17) Uani d . 1 . .
H H12A -0.1044 0.5948 0.7926 0.172 Uiso calc R 1 . .
H H12B 0.0277 0.6528 0.8267 0.172 Uiso calc R 1 . .
H H12C -0.0695 0.546 0.8484 0.172 Uiso calc R 1 . .
C C13 0.1505(2) 0.5247(2) 0.76156(8) 0.0333(5) Uani d . 1 . .
C C14 0.2719(2) 0.5992(2) 0.77392(8) 0.0328(5) Uani d . 1 . .
C C15 0.4253(4) 0.8710(3) 0.76720(18) 0.1013(14) Uani d . 1 . .
H H15A 0.5063 0.9179 0.7835 0.152 Uiso calc R 1 . .
H H15B 0.3518 0.8636 0.7898 0.152 Uiso calc R 1 . .
H H15C 0.3873 0.917 0.7373 0.152 Uiso calc R 1 . .
C C16 0.3125(3) 0.2824(3) 0.52268(11) 0.0606(8) Uani d . 1 . .
H H16 0.3229 0.2742 0.4884 0.073 Uiso calc R 1 . .
C C17 0.2402(3) 0.3859(3) 0.53939(10) 0.0521(7) Uani d . 1 . .
H H17 0.2008 0.4486 0.5167 0.063 Uiso calc R 1 . .
C C18 0.1537(2) 0.6655(2) 0.57440(8) 0.0357(5) Uani d . 1 . .
C C19 0.0437(3) 0.7434(3) 0.55682(12) 0.0635(8) Uani d . 1 . .
H H19 -0.0503 0.7229 0.5629 0.076 Uiso calc R 1 . .
C C20 0.0703(4) 0.8524(3) 0.53019(16) 0.0972(13) Uani d . 1 . .
H H20 -0.0063 0.9054 0.5177 0.117 Uiso calc R 1 . .
C C21 0.2043(4) 0.8842(3) 0.52173(14) 0.0799(10) Uani d . 1 . .
H H21 0.2209 0.9592 0.5036 0.096 Uiso calc R 1 . .
C C22 0.3143(3) 0.8087(3) 0.53925(11) 0.0645(8) Uani d . 1 . .
H H22 0.4081 0.8319 0.5338 0.077 Uiso calc R 1 . .
C C23 0.2906(3) 0.6982(3) 0.56509(9) 0.0501(7) Uani d . 1 . .
H H23 0.3677 0.6446 0.5765 0.06 Uiso calc R 1 . .
C C24 -0.0585(2) 0.4853(2) 0.60528(8) 0.0346(5) Uani d . 1 . .
C C25 -0.1586(3) 0.5710(3) 0.61950(10) 0.0497(7) Uani d . 1 . .
H H25 -0.1285 0.6505 0.6337 0.06 Uiso calc R 1 . .
C C26 -0.3002(3) 0.5420(3) 0.61323(12) 0.0640(8) Uani d . 1 . .
H H26 -0.368 0.6029 0.6215 0.077 Uiso calc R 1 . .
C C27 -0.3431(3) 0.4249(3) 0.59502(12) 0.0721(10) Uani d . 1 . .
H H27 -0.441 0.4045 0.591 0.087 Uiso calc R 1 . .
C C28 -0.2465(3) 0.3367(3) 0.58253(11) 0.0662(9) Uani d . 1 . .
H H28 -0.2773 0.2546 0.5711 0.079 Uiso calc R 1 . .
C C29 -0.1040(3) 0.3672(3) 0.58646(10) 0.0483(6) Uani d . 1 . .
H H29 -0.0375 0.3075 0.5763 0.058 Uiso calc R 1 . .
C C30 0.1081(2) 0.5048(2) 0.71185(8) 0.0336(5) Uani d . 1 . .
H H30 0.028 0.4524 0.7026 0.04 Uiso calc R 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C5 . 1.786(2) ?
P1 C18 . 1.794(2) ?
P1 C24 . 1.795(2) ?
P1 C4 . 1.800(2) ?
O1 C14 . 1.355(3) ?
O1 H33 . 0.84 ?
C1 C16 . 1.370(4) ?
C1 C2 . 1.377(4) ?
C1 H1 . 0.95 ?
C2 C3 . 1.382(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.386(3) ?
C3 H3 . 0.95 ?
C4 C17 . 1.394(3) ?
C5 C30 . 1.393(3) ?
C5 C6 . 1.398(3) ?
C6 C7 . 1.376(3) ?
C6 H6 . 0.95 ?
C7 C14 . 1.406(3) ?
C7 C8 . 1.518(3) ?
C8 C15 . 1.475(4) ?
C8 C9 . 1.491(4) ?
C8 H8 . 1.0 ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C10 C11 . 1.513(4) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 C12 . 1.496(4) ?
C11 C13 . 1.519(3) ?
C11 H11 . 1.0 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 C30 . 1.385(3) ?
C13 C14 . 1.405(3) ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C16 C17 . 1.384(4) ?
C16 H16 . 0.95 ?
C17 H17 . 0.95 ?
C18 C19 . 1.373(3) ?
C18 C23 . 1.394(3) ?
C19 C20 . 1.388(4) ?
C19 H19 . 0.95 ?
C20 C21 . 1.359(5) ?
C20 H20 . 0.95 ?
C21 C22 . 1.357(5) ?
C21 H21 . 0.95 ?
C22 C23 . 1.385(4) ?
C22 H22 . 0.95 ?
C23 H23 . 0.95 ?
C24 C29 . 1.390(3) ?
C24 C25 . 1.391(3) ?
C25 C26 . 1.373(4) ?
C25 H25 . 0.95 ?
C26 C27 . 1.368(4) ?
C26 H26 . 0.95 ?
C27 C28 . 1.369(4) ?
C27 H27 . 0.95 ?
C28 C29 . 1.384(4) ?
C28 H28 . 0.95 ?
C29 H29 . 0.95 ?
C30 H30 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 P1 C18 . . 110.30(10) ?
C5 P1 C24 . . 108.46(10) ?
C18 P1 C24 . . 110.41(11) ?
C5 P1 C4 . . 110.51(10) ?
C18 P1 C4 . . 108.16(11) ?
C24 P1 C4 . . 109.01(11) ?
C14 O1 H33 . . 109.5 ?
C16 C1 C2 . . 120.5(3) ?
C16 C1 H1 . . 119.7 ?
C2 C1 H1 . . 119.7 ?
C1 C2 C3 . . 120.1(3) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
C2 C3 C4 . . 119.7(2) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C3 C4 C17 . . 119.9(2) ?
C3 C4 P1 . . 120.30(18) ?
C17 C4 P1 . . 119.74(19) ?
C30 C5 C6 . . 119.1(2) ?
C30 C5 P1 . . 120.31(16) ?
C6 C5 P1 . . 120.54(17) ?
C7 C6 C5 . . 121.3(2) ?
C7 C6 H6 . . 119.3 ?
C5 C6 H6 . . 119.3 ?
C6 C7 C14 . . 118.4(2) ?
C6 C7 C8 . . 122.6(2) ?
C14 C7 C8 . . 119.0(2) ?
C15 C8 C9 . . 113.3(3) ?
C15 C8 C7 . . 111.1(2) ?
C9 C8 C7 . . 114.8(2) ?
C15 C8 H8 . . 105.6 ?
C9 C8 H8 . . 105.6 ?
C7 C8 H8 . . 105.6 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C11 C10 H10A . . 109.5 ?
C11 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C11 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C12 C11 C10 . . 112.1(3) ?
C12 C11 C13 . . 110.6(2) ?
C10 C11 C13 . . 113.8(2) ?
C12 C11 H11 . . 106.6 ?
C10 C11 H11 . . 106.6 ?
C13 C11 H11 . . 106.6 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C30 C13 C14 . . 117.7(2) ?
C30 C13 C11 . . 121.3(2) ?
C14 C13 C11 . . 120.9(2) ?
O1 C14 C13 . . 122.4(2) ?
O1 C14 C7 . . 115.82(19) ?
C13 C14 C7 . . 121.8(2) ?
C8 C15 H15A . . 109.5 ?
C8 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C8 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C1 C16 C17 . . 120.2(3) ?
C1 C16 H16 . . 119.9 ?
C17 C16 H16 . . 119.9 ?
C16 C17 C4 . . 119.5(3) ?
C16 C17 H17 . . 120.3 ?
C4 C17 H17 . . 120.3 ?
C19 C18 C23 . . 118.8(2) ?
C19 C18 P1 . . 121.35(19) ?
C23 C18 P1 . . 119.77(19) ?
C18 C19 C20 . . 119.8(3) ?
C18 C19 H19 . . 120.1 ?
C20 C19 H19 . . 120.1 ?
C21 C20 C19 . . 120.9(3) ?
C21 C20 H20 . . 119.5 ?
C19 C20 H20 . . 119.5 ?
C22 C21 C20 . . 120.0(3) ?
C22 C21 H21 . . 120.0 ?
C20 C21 H21 . . 120.0 ?
C21 C22 C23 . . 120.3(3) ?
C21 C22 H22 . . 119.9 ?
C23 C22 H22 . . 119.9 ?
C22 C23 C18 . . 120.2(3) ?
C22 C23 H23 . . 119.9 ?
C18 C23 H23 . . 119.9 ?
C29 C24 C25 . . 118.7(2) ?
C29 C24 P1 . . 121.12(19) ?
C25 C24 P1 . . 120.13(18) ?
C26 C25 C24 . . 120.8(3) ?
C26 C25 H25 . . 119.6 ?
C24 C25 H25 . . 119.6 ?
C27 C26 C25 . . 119.6(3) ?
C27 C26 H26 . . 120.2 ?
C25 C26 H26 . . 120.2 ?
C28 C27 C26 . . 120.8(3) ?
C28 C27 H27 . . 119.6 ?
C26 C27 H27 . . 119.6 ?
C27 C28 C29 . . 120.1(3) ?
C27 C28 H28 . . 120.0 ?
C29 C28 H28 . . 120.0 ?
C28 C29 C24 . . 119.8(3) ?
C28 C29 H29 . . 120.1 ?
C24 C29 H29 . . 120.1 ?
C13 C30 C5 . . 121.6(2) ?
C13 C30 H30 . . 119.2 ?
C5 C30 H30 . . 119.2 ?

####################################################################### 
# 
# 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_220725_17RS106_4
_database_code_depnum_ccdc_archive 'CCDC 2206562'
loop_
_audit_author_name
_audit_author_address
'Yasunori Toda'
;Shinshu University
Japan
;
_audit_update_record             
;
2022-09-12 deposited with the CCDC.	2022-09-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H48 Cl12 N4 O12'
_chemical_formula_iupac          ?
_chemical_formula_weight         1250.26
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.8297(7)
_cell_length_b                   14.5160(18)
_cell_length_c                   17.059(2)
_cell_angle_alpha                80.5156(16)
_cell_angle_beta                 88.5593(16)
_cell_angle_gamma                80.2619(16)
_cell_volume                     1403.3(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2994
_cell_measurement_theta_min      2.4210
_cell_measurement_theta_max      24.0027
_cell_measurement_temperature    93.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.388
_exptl_crystal_size_min          0.286
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640

_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.84

_exptl_special_details           
;
;

_diffrn_ambient_temperature      93.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?
_diffrn_source_power             1.50
_diffrn_source_current           30.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            8423
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         27.72
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;

Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             7201
_reflns_number_gt                5826
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.132
_reflns_Friedel_fraction_max     0.127
_reflns_Friedel_fraction_full    0.162

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0876
_refine_ls_goodness_of_fit_ref   1.250
_refine_ls_restrained_S_all      1.249
_refine_ls_number_reflns         7201
_refine_ls_number_parameters     653
_refine_ls_number_restraints     3
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0334P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.322
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 721 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(3)

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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2010.11.0.0'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 -0.30194(17) 0.67175(9) 0.60778(8) 0.0737(3) Uani d . . . 1 . .
Cl Cl2 0.0152(3) 0.78573(9) 0.53019(10) 0.1068(6) Uani d . . . 1 . .
Cl Cl3 0.0966(2) 0.69641(10) 0.69140(8) 0.0868(4) Uani d . . . 1 . .
Cl Cl4 0.8826(2) 0.31169(9) 0.30555(7) 0.0743(3) Uani d . . . 1 . .
Cl Cl5 1.30620(17) 0.33246(9) 0.37798(8) 0.0726(3) Uani d . . . 1 . .
Cl Cl6 0.9816(3) 0.23318(9) 0.46922(8) 0.0919(4) Uani d . . . 1 . .
Cl Cl7 0.4102(3) 0.20428(8) 0.18255(8) 0.0829(4) Uani d . . . 1 . .
Cl Cl8 0.4842(3) 0.20089(10) 0.01702(8) 0.0962(5) Uani d . . . 1 . .
Cl Cl9 0.7388(2) 0.30798(10) 0.09969(9) 0.0865(4) Uani d . . . 1 . .
Cl Cl10 0.5374(2) 0.76732(9) 0.81263(7) 0.0785(4) Uani d . . . 1 . .
Cl Cl11 0.1402(2) 0.71392(12) 0.89878(10) 0.0979(5) Uani d . . . 1 . .
Cl Cl12 0.4904(3) 0.77942(10) 0.97807(9) 0.0983(5) Uani d . . . 1 . .
O O1 0.3267(4) 0.22088(18) 0.65228(17) 0.0555(7) Uani d . . . 1 . .
O O2 0.2469(5) 0.6051(2) 0.50899(17) 0.0628(8) Uani d . . . 1 . .
O O3 0.6122(5) 0.4251(2) 0.63821(15) 0.0556(7) Uani d . . . 1 . .
H H3 0.649257 0.436539 0.590122 0.083000 Uiso calc U . R 1 . .
O O4 0.6368(5) 0.78675(18) 0.33348(16) 0.0562(7) Uani d . . . 1 . .
O O5 0.5781(5) 0.62227(19) 0.27121(16) 0.0575(7) Uani d . . . 1 . .
H H5 0.500008 0.671848 0.246146 0.086000 Uiso calc U . R 1 . .
O O6 0.7599(5) 0.4210(2) 0.47667(17) 0.0650(8) Uani d . . . 1 . .
O O7 0.2019(5) 0.72425(18) 0.16439(17) 0.0564(7) Uani d . . . 1 . .
O O8 0.2289(5) 0.52870(19) 0.23318(15) 0.0525(7) Uani d . . . 1 . .
H H8 0.345607 0.547113 0.249345 0.079000 Uiso calc U . R 1 . .
O O9 0.2384(6) 0.3908(2) -0.00079(17) 0.0699(8) Uani d . . . 1 . .
O O10 0.7999(5) 0.28068(19) 0.82979(17) 0.0580(7) Uani d . . . 1 . .
O O11 0.8664(5) 0.4673(2) 0.75704(15) 0.0619(8) Uani d . . . 1 . .
H H11 0.778114 0.437345 0.736941 0.093000 Uiso calc U . R 1 . .
O O12 0.5839(7) 0.5773(3) 0.99873(19) 0.0982(12) Uani d . . . 1 . .
N N1 0.1183(6) 0.5141(2) 0.61465(19) 0.0512(8) Uani d . . . 1 . .
H H1 0.041907 0.515077 0.659743 0.061000 Uiso calc U . R 1 . .
N N2 0.9182(6) 0.5002(2) 0.37053(18) 0.0489(8) Uani d . . . 1 . .
H H2 1.005649 0.494517 0.328214 0.059000 Uiso calc U . R 1 . .
N N3 0.2010(6) 0.4047(2) 0.12837(19) 0.0524(8) Uani d . . . 1 . .
H H3A 0.229428 0.373975 0.177002 0.063000 Uiso calc U . R 1 . .
N N4 0.6074(8) 0.5613(3) 0.8711(2) 0.0764(12) Uani d . . . 1 . .
H H4 0.596612 0.591863 0.821955 0.092000 Uiso calc U . R 1 . .
C C1 0.3963(11) -0.0607(4) 0.6296(4) 0.0838(16) Uani d . . . 1 . .
H H1A 0.407847 -0.125682 0.624927 0.101000 Uiso calc U . R 1 . .
C C2 0.2088(10) -0.0163(4) 0.6649(4) 0.0810(15) Uani d . . . 1 . .
H H2A 0.089266 -0.050457 0.685545 0.097000 Uiso calc U . R 1 . .
C C3 0.1901(8) 0.0775(3) 0.6710(3) 0.0636(12) Uani d . . . 1 . .
H H3B 0.056749 0.107882 0.695582 0.076000 Uiso calc U . R 1 . .
C C4 0.3617(7) 0.1285(3) 0.6422(3) 0.0496(9) Uani d . . . 1 . .
C C5 0.5062(7) 0.2747(3) 0.6266(2) 0.0492(9) Uani d . . . 1 . .
H H5A 0.532490 0.277555 0.568793 0.059000 Uiso calc U . R 1 . .
H H5B 0.653713 0.245615 0.654847 0.059000 Uiso calc U . R 1 . .
C C6 0.4244(6) 0.3728(3) 0.6459(2) 0.0444(9) Uani d . . . 1 . .
H H6 0.371363 0.366306 0.702438 0.053000 Uiso calc U . R 1 . .
C C7 0.2199(7) 0.4230(3) 0.5936(2) 0.0494(9) Uani d . . . 1 . .
H H7A 0.271969 0.432614 0.537623 0.059000 Uiso calc U . R 1 . .
H H7B 0.098924 0.382121 0.597785 0.059000 Uiso calc U . R 1 . .
C C8 0.1352(6) 0.5954(3) 0.5693(2) 0.0416(8) Uani d . . . 1 . .
C C9 -0.0078(7) 0.6841(3) 0.5983(2) 0.0474(9) Uani d . . . 1 . .
C C10 0.5701(10) -0.0113(4) 0.6004(3) 0.0829(15) Uani d . . . 1 . .
H H10 0.702087 -0.042550 0.575755 0.100000 Uiso calc U . R 1 . .
C C11 0.5550(8) 0.0833(3) 0.6065(3) 0.0673(12) Uani d . . . 1 . .
H H11A 0.675957 0.117015 0.586442 0.081000 Uiso calc U . R 1 . .
C C12 1.0071(6) 0.3291(3) 0.3944(2) 0.0483(9) Uani d . . . 1 . .
C C13 0.8806(6) 0.4231(3) 0.4185(2) 0.0423(9) Uani d . . . 1 . .
C C14 0.8188(7) 0.5940(3) 0.3860(3) 0.0564(11) Uani d . . . 1 . .
H H14A 0.920065 0.639323 0.361945 0.068000 Uiso calc U . R 1 . .
H H14B 0.816663 0.593477 0.444098 0.068000 Uiso calc U . R 1 . .
C C15 0.5759(7) 0.6281(3) 0.3540(2) 0.0479(9) Uani d . . . 1 . .
H H15 0.473241 0.584146 0.381339 0.058000 Uiso calc U . R 1 . .
C C16 0.4826(7) 0.7260(3) 0.3703(3) 0.0572(11) Uani d . . . 1 . .
H H16A 0.323822 0.747537 0.347964 0.069000 Uiso calc U . R 1 . .
H H16B 0.475653 0.726480 0.428234 0.069000 Uiso calc U . R 1 . .
C C17 0.6023(7) 0.8787(3) 0.3482(2) 0.0501(9) Uani d . . . 1 . .
C C18 0.7726(9) 0.9303(3) 0.3190(3) 0.0716(13) Uani d . . . 1 . .
H H18 0.901245 0.902549 0.290673 0.086000 Uiso calc U . R 1 . .
C C19 0.7543(12) 1.0223(4) 0.3314(4) 0.0902(17) Uani d . . . 1 . .
H H19 0.873038 1.057552 0.311989 0.108000 Uiso calc U . R 1 . .
C C20 0.5703(12) 1.0643(4) 0.3707(4) 0.0878(17) Uani d . . . 1 . .
H H20 0.558397 1.128347 0.378167 0.105000 Uiso calc U . R 1 . .
C C21 0.4156(9) 0.9196(3) 0.3882(3) 0.0720(13) Uani d . . . 1 . .
H H21 0.296524 0.884791 0.408096 0.086000 Uiso calc U . R 1 . .
C C22 0.4044(11) 1.0126(4) 0.3989(4) 0.0906(17) Uani d . . . 1 . .
H H22 0.276066 1.041170 0.426894 0.109000 Uiso calc U . R 1 . .
C C23 0.4674(7) 0.2712(3) 0.0910(2) 0.0475(9) Uani d . . . 1 . .
C C24 0.2870(6) 0.3626(3) 0.0678(2) 0.0453(9) Uani d . . . 1 . .
C C25 0.0636(7) 0.4983(3) 0.1180(2) 0.0593(11) Uani d . . . 1 . .
H H25A -0.086873 0.496128 0.145924 0.071000 Uiso calc U . R 1 . .
H H25B 0.030984 0.521252 0.060830 0.071000 Uiso calc U . R 1 . .
C C26 0.1935(6) 0.5650(3) 0.1510(2) 0.0426(8) Uani d . . . 1 . .
H H26 0.348027 0.564556 0.124155 0.051000 Uiso calc U . R 1 . .
C C27 0.0585(7) 0.6649(3) 0.1375(3) 0.0514(10) Uani d . . . 1 . .
H H27A 0.021693 0.685852 0.080305 0.062000 Uiso calc U . R 1 . .
H H27B -0.089281 0.667742 0.167564 0.062000 Uiso calc U . R 1 . .
C C28 0.1306(7) 0.8208(3) 0.1472(2) 0.0478(9) Uani d . . . 1 . .
C C29 -0.0794(8) 0.8646(3) 0.1108(3) 0.0649(12) Uani d . . . 1 . .
H H29 -0.187062 0.828228 0.095909 0.078000 Uiso calc U . R 1 . .
C C30 -0.1275(10) 0.9622(4) 0.0970(3) 0.0813(15) Uani d . . . 1 . .
H H30 -0.268332 0.992947 0.070786 0.098000 Uiso calc U . R 1 . .
C C31 0.0206(10) 1.0152(4) 0.1197(3) 0.0837(16) Uani d . . . 1 . .
H H31 -0.018137 1.082359 0.110743 0.100000 Uiso calc U . R 1 . .
C C32 0.2845(8) 0.8748(3) 0.1695(3) 0.0617(11) Uani d . . . 1 . .
H H32 0.428322 0.844851 0.194146 0.074000 Uiso calc U . R 1 . .
C C33 0.2290(9) 0.9710(3) 0.1561(3) 0.0791(15) Uani d . . . 1 . .
H H33 0.333946 1.008100 0.171792 0.095000 Uiso calc U . R 1 . .
C C34 0.8615(10) -0.0103(4) 0.8699(3) 0.0852(16) Uani d . . . 1 . .
H H34 0.872613 -0.077254 0.877997 0.102000 Uiso calc U . R 1 . .
C C35 1.0355(10) 0.0289(4) 0.8941(4) 0.0828(15) Uani d . . . 1 . .
H H35 1.167868 -0.010687 0.919783 0.099000 Uiso calc U . R 1 . .
C C36 1.0236(8) 0.1258(3) 0.8819(3) 0.0665(12) Uani d . . . 1 . .
H H36 1.147975 0.152709 0.898666 0.080000 Uiso calc U . R 1 . .
C C37 0.8304(7) 0.1837(3) 0.8454(2) 0.0505(10) Uani d . . . 1 . .
C C38 0.9794(8) 0.3250(3) 0.8555(3) 0.0627(12) Uani d . . . 1 . .
H H38A 1.125096 0.308246 0.826126 0.075000 Uiso calc U . R 1 . .
H H38B 1.009962 0.303441 0.912953 0.075000 Uiso calc U . R 1 . .
C C39 0.8983(7) 0.4301(3) 0.8394(2) 0.0520(10) Uani d . . . 1 . .
H H39 1.022635 0.460247 0.859223 0.062000 Uiso calc U . R 1 . .
C C40 0.6831(11) 0.4575(3) 0.8846(3) 0.0862(16) Uani d . . . 1 . .
H H40A 0.557424 0.426649 0.868077 0.103000 Uiso calc U . R 1 . .
H H40B 0.712261 0.434860 0.942070 0.103000 Uiso calc U . R 1 . .
C C41 0.6526(8) 0.1432(3) 0.8212(3) 0.0582(11) Uani d . . . 1 . .
H H41 0.518780 0.182091 0.795795 0.070000 Uiso calc U . R 1 . .
C C42 0.5558(7) 0.6093(3) 0.9295(3) 0.0596(11) Uani d . . . 1 . .
C C43 0.4419(7) 0.7137(3) 0.9053(2) 0.0559(10) Uani d . . . 1 . .
C C44 0.6695(10) 0.0461(4) 0.8338(3) 0.0775(14) Uani d . . . 1 . .
H H44 0.546532 0.018277 0.817281 0.093000 Uiso calc U . R 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C9 . 1.755(4) ?
Cl2 C9 . 1.743(4) ?
Cl3 C9 . 1.761(4) ?
Cl4 C12 . 1.769(4) ?
Cl5 C12 . 1.767(4) ?
Cl6 C12 . 1.751(4) ?
Cl7 C23 . 1.755(4) ?
Cl8 C23 . 1.740(4) ?
Cl9 C23 . 1.770(4) ?
Cl10 C43 . 1.765(5) ?
Cl11 C43 . 1.764(4) ?
Cl12 C43 . 1.741(4) ?
O1 C4 . 1.360(5) ?
O1 C5 . 1.428(4) ?
O2 C8 . 1.205(4) ?
O3 C6 . 1.425(4) ?
O3 H3 . 0.840000 ?
O4 C17 . 1.379(5) ?
O4 C16 . 1.427(5) ?
O5 C15 . 1.427(5) ?
O5 H5 . 0.840000 ?
O6 C13 . 1.202(4) ?
O7 C28 . 1.377(4) ?
O7 C27 . 1.431(5) ?
O8 C26 . 1.421(4) ?
O8 H8 . 0.840000 ?
O9 C24 . 1.199(4) ?
O10 C37 . 1.370(5) ?
O10 C38 . 1.430(5) ?
O11 C39 . 1.425(4) ?
O11 H11 . 0.840000 ?
O12 C42 . 1.201(5) ?
N1 C8 . 1.317(5) ?
N1 C7 . 1.452(5) ?
N1 H1 . 0.880000 ?
N2 C13 . 1.320(5) ?
N2 C14 . 1.451(5) ?
N2 H2 . 0.880000 ?
N3 C24 . 1.330(5) ?
N3 C25 . 1.442(5) ?
N3 H3A . 0.880000 ?
N4 C42 . 1.308(6) ?
N4 C40 . 1.477(6) ?
N4 H4 . 0.880000 ?
C1 C2 . 1.353(8) ?
C1 C10 . 1.376(8) ?
C1 H1A . 0.950000 ?
C2 C3 . 1.369(6) ?
C2 H2A . 0.950000 ?
C3 C4 . 1.377(6) ?
C3 H3B . 0.950000 ?
C4 C11 . 1.385(6) ?
C5 C6 . 1.510(5) ?
C5 H5A . 0.990000 ?
C5 H5B . 0.990000 ?
C6 C7 . 1.514(5) ?
C6 H6 . 1.000000 ?
C7 H7A . 0.990000 ?
C7 H7B . 0.990000 ?
C8 C9 . 1.557(5) ?
C10 C11 . 1.383(7) ?
C10 H10 . 0.950000 ?
C11 H11A . 0.950000 ?
C12 C13 . 1.550(5) ?
C14 C15 . 1.503(5) ?
C14 H14A . 0.990000 ?
C14 H14B . 0.990000 ?
C15 C16 . 1.502(6) ?
C15 H15 . 1.000000 ?
C16 H16A . 0.990000 ?
C16 H16B . 0.990000 ?
C17 C21 . 1.371(6) ?
C17 C18 . 1.378(6) ?
C18 C19 . 1.372(7) ?
C18 H18 . 0.950000 ?
C19 C20 . 1.360(9) ?
C19 H19 . 0.950000 ?
C20 C22 . 1.354(8) ?
C20 H20 . 0.950000 ?
C21 C22 . 1.382(7) ?
C21 H21 . 0.950000 ?
C22 H22 . 0.950000 ?
C23 C24 . 1.549(5) ?
C25 C26 . 1.510(5) ?
C25 H25A . 0.990000 ?
C25 H25B . 0.990000 ?
C26 C27 . 1.512(5) ?
C26 H26 . 1.000000 ?
C27 H27A . 0.990000 ?
C27 H27B . 0.990000 ?
C28 C32 . 1.386(6) ?
C28 C29 . 1.390(6) ?
C29 C30 . 1.378(7) ?
C29 H29 . 0.950000 ?
C30 C31 . 1.352(8) ?
C30 H30 . 0.950000 ?
C31 C33 . 1.384(7) ?
C31 H31 . 0.950000 ?
C32 C33 . 1.361(6) ?
C32 H32 . 0.950000 ?
C33 H33 . 0.950000 ?
C34 C35 . 1.348(8) ?
C34 C44 . 1.365(7) ?
C34 H34 . 0.950000 ?
C35 C36 . 1.377(7) ?
C35 H35 . 0.950000 ?
C36 C37 . 1.380(6) ?
C36 H36 . 0.950000 ?
C37 C41 . 1.379(6) ?
C38 C39 . 1.500(6) ?
C38 H38A . 0.990000 ?
C38 H38B . 0.990000 ?
C39 C40 . 1.487(6) ?
C39 H39 . 1.000000 ?
C40 H40A . 0.990000 ?
C40 H40B . 0.990000 ?
C41 C44 . 1.376(6) ?
C41 H41 . 0.950000 ?
C42 C43 . 1.541(6) ?
C44 H44 . 0.950000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O1 C5 . . 117.7(3) ?
C6 O3 H3 . . 109.500000 ?
C17 O4 C16 . . 117.8(3) ?
C15 O5 H5 . . 109.500000 ?
C28 O7 C27 . . 117.7(3) ?
C26 O8 H8 . . 109.500000 ?
C37 O10 C38 . . 117.2(3) ?
C39 O11 H11 . . 109.500000 ?
C8 N1 C7 . . 123.0(3) ?
C8 N1 H1 . . 118.500000 ?
C7 N1 H1 . . 118.500000 ?
C13 N2 C14 . . 121.5(4) ?
C13 N2 H2 . . 119.200000 ?
C14 N2 H2 . . 119.200000 ?
C24 N3 C25 . . 123.1(3) ?
C24 N3 H3A . . 118.500000 ?
C25 N3 H3A . . 118.500000 ?
C42 N4 C40 . . 122.4(4) ?
C42 N4 H4 . . 118.800000 ?
C40 N4 H4 . . 118.800000 ?
C2 C1 C10 . . 119.6(5) ?
C2 C1 H1A . . 120.200000 ?
C10 C1 H1A . . 120.200000 ?
C1 C2 C3 . . 120.5(5) ?
C1 C2 H2A . . 119.800000 ?
C3 C2 H2A . . 119.800000 ?
C2 C3 C4 . . 121.0(5) ?
C2 C3 H3B . . 119.500000 ?
C4 C3 H3B . . 119.500000 ?
O1 C4 C3 . . 116.1(4) ?
O1 C4 C11 . . 125.0(4) ?
C3 C4 C11 . . 118.9(4) ?
O1 C5 C6 . . 106.5(3) ?
O1 C5 H5A . . 110.400000 ?
C6 C5 H5A . . 110.400000 ?
O1 C5 H5B . . 110.400000 ?
C6 C5 H5B . . 110.400000 ?
H5A C5 H5B . . 108.600000 ?
O3 C6 C5 . . 110.1(3) ?
O3 C6 C7 . . 111.8(3) ?
C5 C6 C7 . . 110.4(3) ?
O3 C6 H6 . . 108.100000 ?
C5 C6 H6 . . 108.100000 ?
C7 C6 H6 . . 108.100000 ?
N1 C7 C6 . . 113.1(3) ?
N1 C7 H7A . . 109.000000 ?
C6 C7 H7A . . 109.000000 ?
N1 C7 H7B . . 109.000000 ?
C6 C7 H7B . . 109.000000 ?
H7A C7 H7B . . 107.800000 ?
O2 C8 N1 . . 125.7(4) ?
O2 C8 C9 . . 119.5(3) ?
N1 C8 C9 . . 114.8(3) ?
C8 C9 Cl2 . . 110.1(3) ?
C8 C9 Cl1 . . 109.8(3) ?
Cl2 C9 Cl1 . . 108.9(2) ?
C8 C9 Cl3 . . 110.1(3) ?
Cl2 C9 Cl3 . . 109.1(2) ?
Cl1 C9 Cl3 . . 108.9(2) ?
C1 C10 C11 . . 120.8(5) ?
C1 C10 H10 . . 119.600000 ?
C11 C10 H10 . . 119.600000 ?
C10 C11 C4 . . 119.3(5) ?
C10 C11 H11A . . 120.300000 ?
C4 C11 H11A . . 120.300000 ?
C13 C12 Cl6 . . 110.7(3) ?
C13 C12 Cl5 . . 110.8(3) ?
Cl6 C12 Cl5 . . 108.2(2) ?
C13 C12 Cl4 . . 109.3(2) ?
Cl6 C12 Cl4 . . 109.2(2) ?
Cl5 C12 Cl4 . . 108.6(2) ?
O6 C13 N2 . . 125.8(4) ?
O6 C13 C12 . . 119.7(3) ?
N2 C13 C12 . . 114.5(3) ?
N2 C14 C15 . . 113.6(3) ?
N2 C14 H14A . . 108.800000 ?
C15 C14 H14A . . 108.800000 ?
N2 C14 H14B . . 108.800000 ?
C15 C14 H14B . . 108.800000 ?
H14A C14 H14B . . 107.700000 ?
O5 C15 C16 . . 112.6(3) ?
O5 C15 C14 . . 108.3(3) ?
C16 C15 C14 . . 111.5(3) ?
O5 C15 H15 . . 108.100000 ?
C16 C15 H15 . . 108.100000 ?
C14 C15 H15 . . 108.100000 ?
O4 C16 C15 . . 107.2(3) ?
O4 C16 H16A . . 110.300000 ?
C15 C16 H16A . . 110.300000 ?
O4 C16 H16B . . 110.300000 ?
C15 C16 H16B . . 110.300000 ?
H16A C16 H16B . . 108.500000 ?
C21 C17 O4 . . 124.9(4) ?
C21 C17 C18 . . 120.1(4) ?
O4 C17 C18 . . 115.0(4) ?
C19 C18 C17 . . 119.2(5) ?
C19 C18 H18 . . 120.400000 ?
C17 C18 H18 . . 120.400000 ?
C20 C19 C18 . . 121.6(6) ?
C20 C19 H19 . . 119.200000 ?
C18 C19 H19 . . 119.200000 ?
C22 C20 C19 . . 118.4(5) ?
C22 C20 H20 . . 120.800000 ?
C19 C20 H20 . . 120.800000 ?
C17 C21 C22 . . 118.5(5) ?
C17 C21 H21 . . 120.700000 ?
C22 C21 H21 . . 120.700000 ?
C20 C22 C21 . . 122.1(6) ?
C20 C22 H22 . . 118.900000 ?
C21 C22 H22 . . 118.900000 ?
C24 C23 Cl8 . . 110.3(3) ?
C24 C23 Cl7 . . 113.7(3) ?
Cl8 C23 Cl7 . . 109.5(2) ?
C24 C23 Cl9 . . 106.4(3) ?
Cl8 C23 Cl9 . . 109.5(2) ?
Cl7 C23 Cl9 . . 107.4(2) ?
O9 C24 N3 . . 125.3(4) ?
O9 C24 C23 . . 119.6(3) ?
N3 C24 C23 . . 115.1(3) ?
N3 C25 C26 . . 109.8(3) ?
N3 C25 H25A . . 109.700000 ?
C26 C25 H25A . . 109.700000 ?
N3 C25 H25B . . 109.700000 ?
C26 C25 H25B . . 109.700000 ?
H25A C25 H25B . . 108.200000 ?
O8 C26 C25 . . 106.4(3) ?
O8 C26 C27 . . 112.0(3) ?
C25 C26 C27 . . 111.0(3) ?
O8 C26 H26 . . 109.100000 ?
C25 C26 H26 . . 109.100000 ?
C27 C26 H26 . . 109.100000 ?
O7 C27 C26 . . 107.2(3) ?
O7 C27 H27A . . 110.300000 ?
C26 C27 H27A . . 110.300000 ?
O7 C27 H27B . . 110.300000 ?
C26 C27 H27B . . 110.300000 ?
H27A C27 H27B . . 108.500000 ?
O7 C28 C32 . . 115.2(3) ?
O7 C28 C29 . . 124.7(4) ?
C32 C28 C29 . . 120.1(4) ?
C30 C29 C28 . . 118.4(5) ?
C30 C29 H29 . . 120.800000 ?
C28 C29 H29 . . 120.800000 ?
C31 C30 C29 . . 121.7(5) ?
C31 C30 H30 . . 119.100000 ?
C29 C30 H30 . . 119.100000 ?
C30 C31 C33 . . 119.6(5) ?
C30 C31 H31 . . 120.200000 ?
C33 C31 H31 . . 120.200000 ?
C33 C32 C28 . . 119.8(4) ?
C33 C32 H32 . . 120.100000 ?
C28 C32 H32 . . 120.100000 ?
C32 C33 C31 . . 120.4(5) ?
C32 C33 H33 . . 119.800000 ?
C31 C33 H33 . . 119.800000 ?
C35 C34 C44 . . 120.0(5) ?
C35 C34 H34 . . 120.000000 ?
C44 C34 H34 . . 120.000000 ?
C34 C35 C36 . . 120.8(5) ?
C34 C35 H35 . . 119.600000 ?
C36 C35 H35 . . 119.600000 ?
C35 C36 C37 . . 119.8(5) ?
C35 C36 H36 . . 120.100000 ?
C37 C36 H36 . . 120.100000 ?
O10 C37 C41 . . 115.9(4) ?
O10 C37 C36 . . 125.0(4) ?
C41 C37 C36 . . 119.1(4) ?
O10 C38 C39 . . 107.8(3) ?
O10 C38 H38A . . 110.200000 ?
C39 C38 H38A . . 110.200000 ?
O10 C38 H38B . . 110.200000 ?
C39 C38 H38B . . 110.200000 ?
H38A C38 H38B . . 108.500000 ?
O11 C39 C40 . . 110.6(4) ?
O11 C39 C38 . . 113.3(3) ?
C40 C39 C38 . . 111.3(4) ?
O11 C39 H39 . . 107.100000 ?
C40 C39 H39 . . 107.100000 ?
C38 C39 H39 . . 107.100000 ?
N4 C40 C39 . . 111.4(4) ?
N4 C40 H40A . . 109.400000 ?
C39 C40 H40A . . 109.400000 ?
N4 C40 H40B . . 109.400000 ?
C39 C40 H40B . . 109.400000 ?
H40A C40 H40B . . 108.000000 ?
C44 C41 C37 . . 119.8(4) ?
C44 C41 H41 . . 120.100000 ?
C37 C41 H41 . . 120.100000 ?
O12 C42 N4 . . 125.0(4) ?
O12 C42 C43 . . 119.1(4) ?
N4 C42 C43 . . 115.8(4) ?
C42 C43 Cl12 . . 110.4(3) ?
C42 C43 Cl10 . . 113.6(3) ?
Cl12 C43 Cl10 . . 109.3(2) ?
C42 C43 Cl11 . . 106.3(3) ?
Cl12 C43 Cl11 . . 108.8(2) ?
Cl10 C43 Cl11 . . 108.3(2) ?
C34 C44 C41 . . 120.5(5) ?
C34 C44 H44 . . 119.800000 ?
C41 C44 H44 . . 119.800000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 C1 C2 C3 . . . . 0.6(9) ?
C1 C2 C3 C4 . . . . -0.5(8) ?
C5 O1 C4 C3 . . . . 177.0(3) ?
C5 O1 C4 C11 . . . . -2.3(6) ?
C2 C3 C4 O1 . . . . -179.2(4) ?
C2 C3 C4 C11 . . . . 0.0(7) ?
C4 O1 C5 C6 . . . . -179.1(3) ?
O1 C5 C6 O3 . . . . 167.5(3) ?
O1 C5 C6 C7 . . . . -68.6(4) ?
C8 N1 C7 C6 . . . . 110.3(4) ?
O3 C6 C7 N1 . . . . -62.9(4) ?
C5 C6 C7 N1 . . . . 174.2(3) ?
C7 N1 C8 O2 . . . . -5.2(6) ?
C7 N1 C8 C9 . . . . 173.8(3) ?
O2 C8 C9 Cl2 . . . . 2.8(5) ?
N1 C8 C9 Cl2 . . . . -176.3(3) ?
O2 C8 C9 Cl1 . . . . 122.7(3) ?
N1 C8 C9 Cl1 . . . . -56.5(4) ?
O2 C8 C9 Cl3 . . . . -117.5(4) ?
N1 C8 C9 Cl3 . . . . 63.3(4) ?
C2 C1 C10 C11 . . . . -0.2(9) ?
C1 C10 C11 C4 . . . . -0.3(8) ?
O1 C4 C11 C10 . . . . 179.6(4) ?
C3 C4 C11 C10 . . . . 0.4(7) ?
C14 N2 C13 O6 . . . . 2.2(6) ?
C14 N2 C13 C12 . . . . -178.0(3) ?
Cl6 C12 C13 O6 . . . . -9.2(5) ?
Cl5 C12 C13 O6 . . . . -129.2(3) ?
Cl4 C12 C13 O6 . . . . 111.2(4) ?
Cl6 C12 C13 N2 . . . . 171.1(3) ?
Cl5 C12 C13 N2 . . . . 51.1(4) ?
Cl4 C12 C13 N2 . . . . -68.6(4) ?
C13 N2 C14 C15 . . . . -85.7(4) ?
N2 C14 C15 O5 . . . . -54.6(4) ?
N2 C14 C15 C16 . . . . -179.0(4) ?
C17 O4 C16 C15 . . . . -172.5(3) ?
O5 C15 C16 O4 . . . . -63.0(4) ?
C14 C15 C16 O4 . . . . 59.0(4) ?
C16 O4 C17 C21 . . . . -7.8(6) ?
C16 O4 C17 C18 . . . . 172.5(4) ?
C21 C17 C18 C19 . . . . 0.9(7) ?
O4 C17 C18 C19 . . . . -179.5(4) ?
C17 C18 C19 C20 . . . . -1.0(9) ?
C18 C19 C20 C22 . . . . 0.9(9) ?
O4 C17 C21 C22 . . . . 179.8(4) ?
C18 C17 C21 C22 . . . . -0.6(7) ?
C19 C20 C22 C21 . . . . -0.7(10) ?
C17 C21 C22 C20 . . . . 0.5(9) ?
C25 N3 C24 O9 . . . . -9.9(6) ?
C25 N3 C24 C23 . . . . 168.8(3) ?
Cl8 C23 C24 O9 . . . . -23.3(5) ?
Cl7 C23 C24 O9 . . . . -146.7(3) ?
Cl9 C23 C24 O9 . . . . 95.3(4) ?
Cl8 C23 C24 N3 . . . . 157.9(3) ?
Cl7 C23 C24 N3 . . . . 34.6(4) ?
Cl9 C23 C24 N3 . . . . -83.5(4) ?
C24 N3 C25 C26 . . . . -114.4(4) ?
N3 C25 C26 O8 . . . . -60.7(4) ?
N3 C25 C26 C27 . . . . 177.3(3) ?
C28 O7 C27 C26 . . . . 170.5(3) ?
O8 C26 C27 O7 . . . . 66.0(4) ?
C25 C26 C27 O7 . . . . -175.3(3) ?
C27 O7 C28 C32 . . . . -175.4(4) ?
C27 O7 C28 C29 . . . . 5.1(6) ?
O7 C28 C29 C30 . . . . -179.7(5) ?
C32 C28 C29 C30 . . . . 0.8(7) ?
C28 C29 C30 C31 . . . . -1.8(8) ?
C29 C30 C31 C33 . . . . 1.6(9) ?
O7 C28 C32 C33 . . . . -179.2(4) ?
C29 C28 C32 C33 . . . . 0.3(7) ?
C28 C32 C33 C31 . . . . -0.5(8) ?
C30 C31 C33 C32 . . . . -0.4(9) ?
C44 C34 C35 C36 . . . . -0.8(9) ?
C34 C35 C36 C37 . . . . 0.7(9) ?
C38 O10 C37 C41 . . . . 178.9(4) ?
C38 O10 C37 C36 . . . . -1.9(6) ?
C35 C36 C37 O10 . . . . -179.5(5) ?
C35 C36 C37 C41 . . . . -0.4(7) ?
C37 O10 C38 C39 . . . . -174.5(3) ?
O10 C38 C39 O11 . . . . -64.0(5) ?
O10 C38 C39 C40 . . . . 61.4(5) ?
C42 N4 C40 C39 . . . . -130.4(5) ?
O11 C39 C40 N4 . . . . -55.1(6) ?
C38 C39 C40 N4 . . . . 178.0(4) ?
O10 C37 C41 C44 . . . . 179.4(4) ?
C36 C37 C41 C44 . . . . 0.2(7) ?
C40 N4 C42 O12 . . . . 7.2(8) ?
C40 N4 C42 C43 . . . . -170.3(4) ?
O12 C42 C43 Cl12 . . . . 26.5(5) ?
N4 C42 C43 Cl12 . . . . -155.8(4) ?
O12 C42 C43 Cl10 . . . . 149.8(4) ?
N4 C42 C43 Cl10 . . . . -32.6(5) ?
O12 C42 C43 Cl11 . . . . -91.2(5) ?
N4 C42 C43 Cl11 . . . . 86.4(4) ?
C35 C34 C44 C41 . . . . 0.6(9) ?
C37 C41 C44 C34 . . . . -0.3(8) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C38 H38B O9 1_656 0.99 2.61 3.263(5) 123.3 ?
C32 H32 O4 . 0.95 2.64 3.449(5) 143.2 ?
C26 H26 O12 1_554 1.00 2.51 3.413(5) 149.7 ?
C21 H21 Cl2 . 0.95 2.96 3.846(5) 156.6 ?
C16 H16B O2 . 0.99 2.58 3.139(5) 115.3 ?
C15 H15 O2 . 1.00 2.55 3.234(5) 125.2 ?
N4 H4 Cl10 . 0.88 2.49 2.955(4) 113.6 ?
N3 H3A Cl7 . 0.88 2.50 2.962(3) 113.6 ?
N2 H2 O8 1_655 0.88 2.10 2.943(4) 159.9 ?
N1 H1 O11 1_455 0.88 2.01 2.852(4) 158.6 ?
O11 H11 O3 . 0.84 2.01 2.748(4) 146.0 ?
O8 H8 O5 . 0.84 1.96 2.775(4) 164.7 ?
O5 H5 O7 . 0.84 2.21 2.922(4) 143.0 ?
O3 H3 O6 . 0.84 2.06 2.873(4) 162.8 ?
C38 H38B O9 1_656 0.99 2.61 3.263(5) 123.3 ?
C32 H32 O4 . 0.95 2.64 3.449(5) 143.2 ?
C26 H26 O12 1_554 1.00 2.51 3.413(5) 149.7 ?
C21 H21 Cl2 . 0.95 2.96 3.846(5) 156.6 ?
C16 H16B O2 . 0.99 2.58 3.139(5) 115.3 ?
C15 H15 O2 . 1.00 2.55 3.234(5) 125.2 ?
N4 H4 Cl10 . 0.88 2.49 2.955(4) 113.6 ?
N3 H3A Cl7 . 0.88 2.50 2.962(3) 113.6 ?
N2 H2 O8 1_655 0.88 2.10 2.943(4) 159.9 ?
N1 H1 O11 1_455 0.88 2.01 2.852(4) 158.6 ?
O11 H11 O3 . 0.84 2.01 2.748(4) 146.0 ?
O8 H8 O5 . 0.84 1.96 2.775(4) 164.7 ?
O5 H5 O7 . 0.84 2.21 2.922(4) 143.0 ?
O3 H3 O6 . 0.84 2.06 2.873(4) 162.8 ?
C38 H38B O9 1_656 0.99 2.61 3.263(5) 123.3 ?
C32 H32 O4 . 0.95 2.64 3.449(5) 143.2 ?
C26 H26 O12 1_554 1.00 2.51 3.413(5) 149.7 ?
C21 H21 Cl2 . 0.95 2.96 3.846(5) 156.6 ?
C16 H16B O2 . 0.99 2.58 3.139(5) 115.3 ?
C15 H15 O2 . 1.00 2.55 3.234(5) 125.2 ?
N4 H4 Cl10 . 0.88 2.49 2.955(4) 113.6 ?
N3 H3A Cl7 . 0.88 2.50 2.962(3) 113.6 ?
N2 H2 O8 1_655 0.88 2.10 2.943(4) 159.9 ?
N1 H1 O11 1_455 0.88 2.01 2.852(4) 158.6 ?
O11 H11 O3 . 0.84 2.01 2.748(4) 146.0 ?
O8 H8 O5 . 0.84 1.96 2.775(4) 164.7 ?
O5 H5 O7 . 0.84 2.21 2.922(4) 143.0 ?
O3 H3 O6 . 0.84 2.06 2.873(4) 162.8 ?
O3 H3 O6 . 0.84 2.06 2.873(4) 162.8 ?
O5 H5 O7 . 0.84 2.21 2.922(4) 143.0 ?
O8 H8 O5 . 0.84 1.96 2.775(4) 164.7 ?
O11 H11 O3 . 0.84 2.01 2.748(4) 146.0 ?
N1 H1 O11 1_455 0.88 2.01 2.852(4) 158.6 ?
N2 H2 O8 1_655 0.88 2.10 2.943(4) 159.9 ?
N3 H3A Cl7 . 0.88 2.50 2.962(3) 113.6 ?
N4 H4 Cl10 . 0.88 2.49 2.955(4) 113.6 ?
C15 H15 O2 . 1.00 2.55 3.234(5) 125.2 ?
C16 H16B O2 . 0.99 2.58 3.139(5) 115.3 ?
C21 H21 Cl2 . 0.95 2.96 3.846(5) 156.6 ?
C26 H26 O12 1_554 1.00 2.51 3.413(5) 149.7 ?
C32 H32 O4 . 0.95 2.64 3.449(5) 143.2 ?
C38 H38B O9 1_656 0.99 2.61 3.263(5) 123.3 ?
O3 H3 O6 . 0.84 2.06 2.873(4) 162.8 ?
O5 H5 O7 . 0.84 2.21 2.922(4) 143.0 ?
O8 H8 O5 . 0.84 1.96 2.775(4) 164.7 ?
O11 H11 O3 . 0.84 2.01 2.748(4) 146.0 ?
N1 H1 O11 1_455 0.88 2.01 2.852(4) 158.6 ?
N2 H2 O8 1_655 0.88 2.10 2.943(4) 159.9 ?
N3 H3A Cl7 . 0.88 2.50 2.962(3) 113.6 ?
N4 H4 Cl10 . 0.88 2.49 2.955(4) 113.6 ?
C15 H15 O2 . 1.00 2.55 3.234(5) 125.2 ?
C16 H16B O2 . 0.99 2.58 3.139(5) 115.3 ?
C21 H21 Cl2 . 0.95 2.96 3.846(5) 156.6 ?
C26 H26 O12 1_554 1.00 2.51 3.413(5) 149.7 ?
C32 H32 O4 . 0.95 2.64 3.449(5) 143.2 ?
C38 H38B O9 1_656 0.99 2.61 3.263(5) 123.3 ?
O3 H3 O6 . 0.84 2.06 2.873(4) 162.8 ?
O5 H5 O7 . 0.84 2.21 2.922(4) 143.0 ?
O8 H8 O5 . 0.84 1.96 2.775(4) 164.7 ?
O11 H11 O3 . 0.84 2.01 2.748(4) 146.0 ?
N1 H1 O11 1_455 0.88 2.01 2.852(4) 158.6 ?
N2 H2 O8 1_655 0.88 2.10 2.943(4) 159.9 ?
N3 H3A Cl7 . 0.88 2.50 2.962(3) 113.6 ?
N4 H4 Cl10 . 0.88 2.49 2.955(4) 113.6 ?
C15 H15 O2 . 1.00 2.55 3.234(5) 125.2 ?
C16 H16B O2 . 0.99 2.58 3.139(5) 115.3 ?
C21 H21 Cl2 . 0.95 2.96 3.846(5) 156.6 ?
C26 H26 O12 1_554 1.00 2.51 3.413(5) 149.7 ?
C32 H32 O4 . 0.95 2.64 3.449(5) 143.2 ?
C38 H38B O9 1_656 0.99 2.61 3.263(5) 123.3 ?



