#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:39:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180348 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/17/7201790.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7201790
loop_
_publ_author_name
'Lavy, Tali'
'Sheynin, Yana'
'Sparkes, Hazel A.'
'Howard, Judith A. K.'
'Kaftory, Menahem'
_publ_section_title
;
 Controlled photochemical reaction of 4-oxo(phenylacetyl)morpholine and
 1-(phenylglyoxylyl)piperidine in solid supramolecular systems
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              734
_journal_paper_doi               10.1039/b715981a
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H20 Cl2 O2, C12 H13 N O3'
_chemical_formula_sum            'C42 H33 Cl2 N O5'
_chemical_formula_weight         702.59
_chemical_name_common
;
2,4-hexadiyne-1,6-diol-1,6-bis(2-chlorophenyl)-1,6-diphenyl,
4-oxo(phenylacetyl)morpholine clathrate
;
_chemical_name_systematic
;
2,4-hexadiyne-1,6-diol-1,6-bis(2-chlorophenyl)-1,6-diphenyl,
4-oxo(phenylacetyl)morpholine clathrate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.8526(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2078(2)
_cell_length_b                   24.8368(7)
_cell_length_c                   9.4738(3)
_cell_measurement_reflns_used    3583
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      1.018
_cell_volume                     1792.51(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_av_sigmaI/netI    0.1478
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12082
_diffrn_reflns_theta_full        27.35
_diffrn_reflns_theta_max         27.35
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.92(8)
_refine_ls_extinction_coef       0.027(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.819
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         7122
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      0.818
_refine_ls_R_factor_all          0.1424
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0663P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1565
_reflns_number_gt                3098
_reflns_number_total             7122
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b715981a.txt
_cod_data_source_block           IVa
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7201790
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1A Cl 0.64946(17) 0.26390(6) 0.93636(16) 0.0821(4) Uani 1 1 d . . .
O1A O 0.1092(4) 0.25323(13) 0.9651(3) 0.0623(8) Uani 1 1 d . . .
H1A H 0.0971 0.2760 1.0230 0.093 Uiso 1 1 calc R . .
C1A C 0.2996(6) 0.3678(2) 0.9011(5) 0.0579(12) Uani 1 1 d . . .
C2A C 0.2890(6) 0.32011(19) 0.9179(5) 0.0535(11) Uani 1 1 d . . .
C3A C 0.2706(5) 0.26218(17) 0.9449(5) 0.0502(10) Uani 1 1 d . . .
C4A C 0.4319(6) 0.24671(16) 1.0910(5) 0.0546(11) Uani 1 1 d . . .
C5A C 0.4050(7) 0.23335(18) 1.2233(6) 0.0648(13) Uani 1 1 d . . .
H5A H 0.2919 0.2320 1.2235 0.078 Uiso 1 1 calc R . .
C6A C 0.5491(8) 0.2220(2) 1.3558(6) 0.0735(14) Uani 1 1 d . . .
H6A H 0.5312 0.2128 1.4441 0.088 Uiso 1 1 calc R . .
C7A C 0.7140(8) 0.2240(2) 1.3575(7) 0.0774(15) Uani 1 1 d . . .
H7A H 0.8081 0.2172 1.4478 0.093 Uiso 1 1 calc R . .
C8A C 0.7452(7) 0.2358(2) 1.2310(7) 0.0739(15) Uani 1 1 d . . .
H8A H 0.8591 0.2357 1.2323 0.089 Uiso 1 1 calc R . .
C9A C 0.5996(7) 0.24832(17) 1.0949(5) 0.0598(12) Uani 1 1 d . . .
C10A C 0.2568(6) 0.22677(19) 0.8083(5) 0.0578(12) Uani 1 1 d . . .
C11A C 0.2092(6) 0.2492(2) 0.6646(6) 0.0730(14) Uani 1 1 d . . .
H11A H 0.1877 0.2859 0.6489 0.088 Uiso 1 1 calc R . .
C12A C 0.1948(7) 0.2145(4) 0.5438(7) 0.0969(19) Uani 1 1 d . . .
H12A H 0.1662 0.2288 0.4468 0.116 Uiso 1 1 calc R . .
C13A C 0.2209(9) 0.1614(4) 0.5635(9) 0.108(2) Uani 1 1 d . . .
H13A H 0.2049 0.1395 0.4798 0.130 Uiso 1 1 calc R . .
C14A C 0.2720(10) 0.1385(3) 0.7087(10) 0.115(2) Uani 1 1 d . . .
H14A H 0.2953 0.1018 0.7240 0.139 Uiso 1 1 calc R . .
C15A C 0.2865(8) 0.1726(2) 0.8290(7) 0.0851(17) Uani 1 1 d . . .
H15A H 0.3171 0.1583 0.9262 0.102 Uiso 1 1 calc R . .
Cl1B Cl -0.04317(19) 0.49436(6) 0.62132(16) 0.0915(5) Uani 1 1 d . . .
O1B O 0.4935(5) 0.54886(14) 0.9441(4) 0.0823(11) Uani 1 1 d . . .
H1B H 0.602(9) 0.533(3) 0.928(7) 0.123 Uiso 1 1 d . . .
C1B C 0.3145(6) 0.4222(2) 0.8815(5) 0.0615(13) Uani 1 1 d . . .
C2B C 0.3258(6) 0.4695(2) 0.8615(6) 0.0628(13) Uani 1 1 d . . .
C3B C 0.3360(6) 0.52733(18) 0.8298(6) 0.0636(13) Uani 1 1 d . . .
C4B C 0.1819(7) 0.55701(18) 0.8452(5) 0.0600(12) Uani 1 1 d . . .
C5B C 0.2102(9) 0.5999(2) 0.9497(6) 0.0775(16) Uani 1 1 d . . .
H5B H 0.3247 0.6093 1.0104 0.093 Uiso 1 1 calc R . .
C6B C 0.0770(11) 0.6275(2) 0.9639(7) 0.0871(18) Uani 1 1 d . . .
H6B H 0.1003 0.6561 1.0317 0.105 Uiso 1 1 calc R . .
C7B C -0.0946(12) 0.6138(3) 0.8787(9) 0.105(2) Uani 1 1 d . . .
H7B H -0.1871 0.6321 0.8913 0.126 Uiso 1 1 calc R . .
C8B C -0.1272(8) 0.5717(2) 0.7728(7) 0.0825(16) Uani 1 1 d . . .
H8B H -0.2417 0.5621 0.7132 0.099 Uiso 1 1 calc R . .
C9B C 0.0087(7) 0.5457(2) 0.7588(6) 0.0667(14) Uani 1 1 d . . .
C10B C 0.3497(6) 0.53652(18) 0.6750(6) 0.0653(13) Uani 1 1 d . . .
C11B C 0.2973(11) 0.5843(2) 0.5983(9) 0.116(2) Uani 1 1 d . . .
H11B H 0.2461 0.6108 0.6378 0.140 Uiso 1 1 calc R . .
C12B C 0.3204(12) 0.5934(3) 0.4619(9) 0.129(3) Uani 1 1 d . . .
H12B H 0.2840 0.6260 0.4116 0.154 Uiso 1 1 calc R . .
C13B C 0.3944(9) 0.5560(3) 0.4009(7) 0.0954(19) Uani 1 1 d . . .
H13B H 0.4062 0.5623 0.3085 0.114 Uiso 1 1 calc R . .
C14B C 0.4505(8) 0.5096(3) 0.4756(8) 0.0884(18) Uani 1 1 d . . .
H14B H 0.5061 0.4844 0.4365 0.106 Uiso 1 1 calc R . .
C15B C 0.4269(6) 0.4987(2) 0.6108(6) 0.0724(14) Uani 1 1 d . . .
H15B H 0.4631 0.4658 0.6588 0.087 Uiso 1 1 calc R . .
N1 N 0.0053(8) 0.4061(2) 0.1763(6) 0.123(2) Uani 1 1 d . . .
O2 O 0.1643(5) 0.37735(16) 0.5100(4) 0.0805(10) Uani 1 1 d . . .
O3 O 0.0877(4) 0.31953(15) 0.1954(4) 0.0765(10) Uani 1 1 d . . .
O4 O -0.1963(6) 0.48879(19) 0.0085(5) 0.1129(15) Uani 1 1 d . . .
C16 C 0.2295(6) 0.37099(18) 0.4143(6) 0.0581(12) Uani 1 1 d . . .
C17 C 0.4130(6) 0.36385(18) 0.4444(5) 0.0565(12) Uani 1 1 d . . .
C18 C 0.5267(7) 0.3499(2) 0.5936(6) 0.0665(13) Uani 1 1 d . . .
H18 H 0.4830 0.3450 0.6702 0.080 Uiso 1 1 calc R . .
C19 C 0.6987(7) 0.3440(2) 0.6226(7) 0.0806(16) Uani 1 1 d . . .
H19 H 0.7719 0.3339 0.7202 0.097 Uiso 1 1 calc R . .
C20 C 0.7715(8) 0.3519(3) 0.5173(9) 0.0921(19) Uani 1 1 d . . .
H20 H 0.8920 0.3488 0.5426 0.111 Uiso 1 1 calc R . .
C21 C 0.6616(9) 0.3646(2) 0.3720(8) 0.0858(17) Uani 1 1 d . . .
H21 H 0.7081 0.3698 0.2972 0.103 Uiso 1 1 calc R . .
C22 C 0.4840(7) 0.3697(2) 0.3354(6) 0.0690(14) Uani 1 1 d . . .
H22 H 0.4113 0.3773 0.2357 0.083 Uiso 1 1 calc R . .
C23 C 0.0985(7) 0.3658(2) 0.2483(6) 0.0716(14) Uani 1 1 d . . .
C24 C -0.152(2) 0.3954(4) 0.0359(10) 0.073(3) Uani 0.59 1 d PD . .
H24A H -0.2571 0.3924 0.0587 0.087 Uiso 0.59 1 calc PR . .
H24B H -0.1368 0.3627 -0.0139 0.087 Uiso 0.59 1 calc PR . .
C25 C -0.159(2) 0.4450(5) -0.0625(14) 0.091(4) Uani 0.59 1 d PD . .
H25A H -0.0469 0.4500 -0.0735 0.109 Uiso 0.59 1 calc PR . .
H25B H -0.2489 0.4404 -0.1629 0.109 Uiso 0.59 1 calc PR . .
C26 C -0.035(2) 0.5037(4) 0.1433(13) 0.083(4) Uani 0.59 1 d PD . .
H26A H -0.0503 0.5381 0.1852 0.099 Uiso 0.59 1 calc PR . .
H26B H 0.0671 0.5057 0.1152 0.099 Uiso 0.59 1 calc PR . .
C27 C -0.015(2) 0.4580(3) 0.2582(11) 0.069(3) Uani 0.59 1 d PD . .
H27A H 0.0880 0.4638 0.3499 0.083 Uiso 0.59 1 calc PR . .
H27B H -0.1174 0.4558 0.2854 0.083 Uiso 0.59 1 calc PR . .
C28 C 0.073(2) 0.4661(7) 0.194(3) 0.103(6) Uani 0.41 1 d PD . .
H28A H 0.1061 0.4783 0.1117 0.124 Uiso 0.41 1 calc PR . .
H28B H 0.1651 0.4735 0.2921 0.124 Uiso 0.41 1 calc PR . .
C29 C -0.2380(19) 0.4252(10) -0.025(3) 0.089(5) Uani 0.41 1 d PD . .
H29A H -0.2764 0.4091 0.0509 0.107 Uiso 0.41 1 calc PR . .
H29B H -0.3272 0.4195 -0.1250 0.107 Uiso 0.41 1 calc PR . .
C30 C -0.0599(16) 0.4024(8) -0.014(2) 0.085(5) Uani 0.41 1 d PD . .
H30A H 0.0048 0.4257 -0.0567 0.102 Uiso 0.41 1 calc PR . .
H30B H -0.0659 0.3659 -0.0526 0.102 Uiso 0.41 1 calc PR . .
C31 C -0.109(2) 0.4860(10) 0.183(2) 0.103(7) Uani 0.41 1 d PD . .
H31A H -0.1671 0.4605 0.2260 0.124 Uiso 0.41 1 calc PR . .
H31B H -0.1035 0.5210 0.2299 0.124 Uiso 0.41 1 calc PR . .
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'
N N 0.0061 0.0033 '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'
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
C3A O1A H1A 109.5 . . ?
C2A C1A C1B 179.0(5) . . ?
C1A C2A C3A 176.6(5) . . ?
O1A C3A C2A 109.6(3) . . ?
O1A C3A C10A 104.1(3) . . ?
C2A C3A C10A 113.1(4) . . ?
O1A C3A C4A 111.4(3) . . ?
C2A C3A C4A 106.5(3) . . ?
C10A C3A C4A 112.2(3) . . ?
C9A C4A C5A 118.7(4) . . ?
C9A C4A C3A 122.0(4) . . ?
C5A C4A C3A 119.3(4) . . ?
C6A C5A C4A 119.5(5) . . ?
C6A C5A H5A 120.2 . . ?
C4A C5A H5A 120.2 . . ?
C5A C6A C7A 121.0(5) . . ?
C5A C6A H6A 119.5 . . ?
C7A C6A H6A 119.5 . . ?
C8A C7A C6A 121.3(5) . . ?
C8A C7A H7A 119.4 . . ?
C6A C7A H7A 119.4 . . ?
C7A C8A C9A 118.6(5) . . ?
C7A C8A H8A 120.7 . . ?
C9A C8A H8A 120.7 . . ?
C4A C9A C8A 121.0(4) . . ?
C4A C9A Cl1A 122.8(4) . . ?
C8A C9A Cl1A 116.1(4) . . ?
C11A C10A C15A 120.4(5) . . ?
C11A C10A C3A 120.3(4) . . ?
C15A C10A C3A 119.3(4) . . ?
C10A C11A C12A 117.5(6) . . ?
C10A C11A H11A 121.2 . . ?
C12A C11A H11A 121.2 . . ?
C13A C12A C11A 122.1(6) . . ?
C13A C12A H12A 119.0 . . ?
C11A C12A H12A 119.0 . . ?
C12A C13A C14A 120.8(6) . . ?
C12A C13A H13A 119.6 . . ?
C14A C13A H13A 119.6 . . ?
C15A C14A C13A 117.3(7) . . ?
C15A C14A H14A 121.3 . . ?
C13A C14A H14A 121.3 . . ?
C14A C15A C10A 121.7(6) . . ?
C14A C15A H15A 119.1 . . ?
C10A C15A H15A 119.1 . . ?
C3B O1B H1B 109(4) . . ?
C2B C1B C1A 178.7(5) . . ?
C1B C2B C3B 177.6(5) . . ?
O1B C3B C2B 108.1(4) . . ?
O1B C3B C4B 107.0(4) . . ?
C2B C3B C4B 109.9(4) . . ?
O1B C3B C10B 107.4(4) . . ?
C2B C3B C10B 111.7(4) . . ?
C4B C3B C10B 112.4(4) . . ?
C9B C4B C5B 115.7(5) . . ?
C9B C4B C3B 123.7(4) . . ?
C5B C4B C3B 120.5(5) . . ?
C6B C5B C4B 121.9(6) . . ?
C6B C5B H5B 119.1 . . ?
C4B C5B H5B 119.1 . . ?
C5B C6B C7B 120.6(6) . . ?
C5B C6B H6B 119.7 . . ?
C7B C6B H6B 119.7 . . ?
C8B C7B C6B 118.9(6) . . ?
C8B C7B H7B 120.6 . . ?
C6B C7B H7B 120.6 . . ?
C7B C8B C9B 119.1(6) . . ?
C7B C8B H8B 120.5 . . ?
C9B C8B H8B 120.5 . . ?
C8B C9B C4B 123.8(5) . . ?
C8B C9B Cl1B 116.3(5) . . ?
C4B C9B Cl1B 120.0(4) . . ?
C11B C10B C15B 117.0(5) . . ?
C11B C10B C3B 121.1(5) . . ?
C15B C10B C3B 121.8(5) . . ?
C10B C11B C12B 120.4(6) . . ?
C10B C11B H11B 119.8 . . ?
C12B C11B H11B 119.8 . . ?
C13B C12B C11B 121.6(7) . . ?
C13B C12B H12B 119.2 . . ?
C11B C12B H12B 119.2 . . ?
C14B C13B C12B 119.1(6) . . ?
C14B C13B H13B 120.5 . . ?
C12B C13B H13B 120.5 . . ?
C13B C14B C15B 120.9(6) . . ?
C13B C14B H14B 119.5 . . ?
C15B C14B H14B 119.5 . . ?
C14B C15B C10B 120.9(5) . . ?
C14B C15B H15B 119.5 . . ?
C10B C15B H15B 119.5 . . ?
C23 N1 C24 118.5(6) . . ?
C23 N1 C28 124.2(8) . . ?
C24 N1 C28 114.7(9) . . ?
C23 N1 C27 122.4(6) . . ?
C24 N1 C27 112.3(8) . . ?
C28 N1 C27 41.9(7) . . ?
C23 N1 C30 114.4(7) . . ?
C24 N1 C30 37.7(5) . . ?
C28 N1 C30 97.4(12) . . ?
C27 N1 C30 122.3(8) . . ?
C25 O4 C31 113.0(9) . . ?
C25 O4 C26 108.9(9) . . ?
C31 O4 C26 35.8(7) . . ?
C25 O4 C29 37.2(6) . . ?
C31 O4 C29 98.3(13) . . ?
C26 O4 C29 117.4(8) . . ?
O2 C16 C17 125.8(4) . . ?
O2 C16 C23 115.8(5) . . ?
C17 C16 C23 118.2(5) . . ?
C22 C17 C18 118.1(5) . . ?
C22 C17 C16 123.1(5) . . ?
C18 C17 C16 118.8(5) . . ?
C19 C18 C17 118.9(5) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C20 C19 C18 123.5(6) . . ?
C20 C19 H19 118.2 . . ?
C18 C19 H19 118.2 . . ?
C19 C20 C21 117.9(5) . . ?
C19 C20 H20 121.1 . . ?
C21 C20 H20 121.1 . . ?
C20 C21 C22 120.9(5) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C17 120.6(5) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
O3 C23 N1 124.4(5) . . ?
O3 C23 C16 114.0(4) . . ?
N1 C23 C16 121.5(5) . . ?
N1 C24 C25 102.9(9) . . ?
N1 C24 H24A 111.2 . . ?
C25 C24 H24A 111.2 . . ?
N1 C24 H24B 111.2 . . ?
C25 C24 H24B 111.2 . . ?
H24A C24 H24B 109.1 . . ?
O4 C25 C24 107.7(12) . . ?
O4 C25 H25A 110.2 . . ?
C24 C25 H25A 110.2 . . ?
O4 C25 H25B 110.2 . . ?
C24 C25 H25B 110.2 . . ?
H25A C25 H25B 108.5 . . ?
O4 C26 C27 104.4(10) . . ?
O4 C26 H26A 110.9 . . ?
C27 C26 H26A 110.9 . . ?
O4 C26 H26B 110.9 . . ?
C27 C26 H26B 110.9 . . ?
H26A C26 H26B 108.9 . . ?
N1 C27 C26 105.3(8) . . ?
N1 C27 H27A 110.7 . . ?
C26 C27 H27A 110.7 . . ?
N1 C27 H27B 110.7 . . ?
C26 C27 H27B 110.7 . . ?
H27A C27 H27B 108.8 . . ?
N1 C28 C31 90.2(14) . . ?
N1 C28 H28A 113.6 . . ?
C31 C28 H28A 113.6 . . ?
N1 C28 H28B 113.6 . . ?
C31 C28 H28B 113.6 . . ?
H28A C28 H28B 110.9 . . ?
C30 C29 O4 102.7(15) . . ?
C30 C29 H29A 111.2 . . ?
O4 C29 H29A 111.2 . . ?
C30 C29 H29B 111.2 . . ?
O4 C29 H29B 111.2 . . ?
H29A C29 H29B 109.1 . . ?
C29 C30 N1 88.0(14) . . ?
C29 C30 H30A 114.0 . . ?
N1 C30 H30A 114.0 . . ?
C29 C30 H30B 114.0 . . ?
N1 C30 H30B 114.0 . . ?
H30A C30 H30B 111.2 . . ?
O4 C31 C28 98.2(15) . . ?
O4 C31 H31A 112.1 . . ?
C28 C31 H31A 112.1 . . ?
O4 C31 H31B 112.1 . . ?
C28 C31 H31B 112.1 . . ?
H31A C31 H31B 109.8 . . ?
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
Cl1A C9A 1.741(5) . ?
O1A C3A 1.424(5) . ?
O1A H1A 0.8200 . ?
C1A C2A 1.204(6) . ?
C1A C1B 1.375(7) . ?
C2A C3A 1.479(7) . ?
C3A C10A 1.534(6) . ?
C3A C4A 1.566(6) . ?
C4A C9A 1.363(6) . ?
C4A C5A 1.392(6) . ?
C5A C6A 1.396(7) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.348(7) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.348(7) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.429(7) . ?
C8A H8A 0.9300 . ?
C10A C11A 1.386(6) . ?
C10A C15A 1.368(7) . ?
C11A C12A 1.402(8) . ?
C11A H11A 0.9300 . ?
C12A C13A 1.337(11) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.402(10) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.389(8) . ?
C14A H14A 0.9300 . ?
C15A H15A 0.9300 . ?
Cl1B C9B 1.758(5) . ?
O1B C3B 1.445(6) . ?
O1B H1B 1.04(7) . ?
C1B C2B 1.199(6) . ?
C2B C3B 1.476(7) . ?
C3B C4B 1.518(7) . ?
C3B C10B 1.528(7) . ?
C4B C9B 1.379(7) . ?
C4B C5B 1.414(7) . ?
C5B C6B 1.338(8) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.380(10) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.403(9) . ?
C7B H7B 0.9300 . ?
C8B C9B 1.338(7) . ?
C8B H8B 0.9300 . ?
C10B C11B 1.375(8) . ?
C10B C15B 1.393(7) . ?
C11B C12B 1.392(9) . ?
C11B H11B 0.9300 . ?
C12B C13B 1.352(9) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.340(9) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.391(8) . ?
C14B H14B 0.9300 . ?
C15B H15B 0.9300 . ?
N1 C23 1.291(7) . ?
N1 C24 1.491(12) . ?
N1 C28 1.576(17) . ?
N1 C27 1.543(10) . ?
N1 C30 1.68(2) . ?
O2 C16 1.222(5) . ?
O3 C23 1.243(6) . ?
O4 C25 1.373(15) . ?
O4 C31 1.54(2) . ?
O4 C26 1.504(15) . ?
O4 C29 1.62(2) . ?
C16 C17 1.436(7) . ?
C16 C23 1.545(7) . ?
C17 C22 1.370(7) . ?
C17 C18 1.417(7) . ?
C18 C19 1.342(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.354(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(8) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C24 C25 1.533(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.538(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C31 1.537(5) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.536(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
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
C1B C1A C2A C3A 146(25) . . . . ?
C1A C2A C3A O1A 34(8) . . . . ?
C1A C2A C3A C10A 150(8) . . . . ?
C1A C2A C3A C4A -86(8) . . . . ?
O1A C3A C4A C9A 175.4(4) . . . . ?
C2A C3A C4A C9A -65.2(5) . . . . ?
C10A C3A C4A C9A 59.1(5) . . . . ?
O1A C3A C4A C5A -7.8(5) . . . . ?
C2A C3A C4A C5A 111.7(4) . . . . ?
C10A C3A C4A C5A -124.1(4) . . . . ?
C9A C4A C5A C6A -0.1(6) . . . . ?
C3A C4A C5A C6A -177.0(4) . . . . ?
C4A C5A C6A C7A 0.4(7) . . . . ?
C5A C6A C7A C8A -1.7(8) . . . . ?
C6A C7A C8A C9A 2.5(8) . . . . ?
C5A C4A C9A C8A 1.0(6) . . . . ?
C3A C4A C9A C8A 177.9(4) . . . . ?
C5A C4A C9A Cl1A 179.4(3) . . . . ?
C3A C4A C9A Cl1A -3.7(6) . . . . ?
C7A C8A C9A C4A -2.2(7) . . . . ?
C7A C8A C9A Cl1A 179.2(4) . . . . ?
O1A C3A C10A C11A 99.3(4) . . . . ?
C2A C3A C10A C11A -19.5(5) . . . . ?
C4A C3A C10A C11A -140.0(4) . . . . ?
O1A C3A C10A C15A -78.6(5) . . . . ?
C2A C3A C10A C15A 162.6(4) . . . . ?
C4A C3A C10A C15A 42.1(6) . . . . ?
C15A C10A C11A C12A -0.6(7) . . . . ?
C3A C10A C11A C12A -178.5(4) . . . . ?
C10A C11A C12A C13A 1.7(8) . . . . ?
C11A C12A C13A C14A -2.9(10) . . . . ?
C12A C13A C14A C15A 2.8(10) . . . . ?
C13A C14A C15A C10A -1.7(9) . . . . ?
C11A C10A C15A C14A 0.7(8) . . . . ?
C3A C10A C15A C14A 178.6(5) . . . . ?
C2A C1A C1B C2B 91(37) . . . . ?
C1A C1B C2B C3B -3(35) . . . . ?
C1B C2B C3B O1B -148(13) . . . . ?
C1B C2B C3B C4B 96(13) . . . . ?
C1B C2B C3B C10B -30(13) . . . . ?
O1B C3B C4B C9B -177.2(4) . . . . ?
C2B C3B C4B C9B -60.1(6) . . . . ?
C10B C3B C4B C9B 65.1(5) . . . . ?
O1B C3B C4B C5B 4.5(6) . . . . ?
C2B C3B C4B C5B 121.7(5) . . . . ?
C10B C3B C4B C5B -113.2(5) . . . . ?
C9B C4B C5B C6B 0.4(7) . . . . ?
C3B C4B C5B C6B 178.8(5) . . . . ?
C4B C5B C6B C7B 1.7(9) . . . . ?
C5B C6B C7B C8B -2.3(9) . . . . ?
C6B C7B C8B C9B 0.8(8) . . . . ?
C7B C8B C9B C4B 1.4(8) . . . . ?
C7B C8B C9B Cl1B -178.9(4) . . . . ?
C5B C4B C9B C8B -2.0(7) . . . . ?
C3B C4B C9B C8B 179.7(5) . . . . ?
C5B C4B C9B Cl1B 178.3(4) . . . . ?
C3B C4B C9B Cl1B 0.0(7) . . . . ?
O1B C3B C10B C11B -85.7(7) . . . . ?
C2B C3B C10B C11B 155.9(6) . . . . ?
C4B C3B C10B C11B 31.8(7) . . . . ?
O1B C3B C10B C15B 89.6(5) . . . . ?
C2B C3B C10B C15B -28.8(7) . . . . ?
C4B C3B C10B C15B -152.9(5) . . . . ?
C15B C10B C11B C12B 0.6(10) . . . . ?
C3B C10B C11B C12B 176.0(6) . . . . ?
C10B C11B C12B C13B -0.1(12) . . . . ?
C11B C12B C13B C14B -1.6(12) . . . . ?
C12B C13B C14B C15B 2.7(10) . . . . ?
C13B C14B C15B C10B -2.3(8) . . . . ?
C11B C10B C15B C14B 0.6(8) . . . . ?
C3B C10B C15B C14B -174.9(5) . . . . ?
O2 C16 C17 C22 -163.8(5) . . . . ?
C23 C16 C17 C22 21.5(7) . . . . ?
O2 C16 C17 C18 16.3(7) . . . . ?
C23 C16 C17 C18 -158.4(4) . . . . ?
C22 C17 C18 C19 1.1(7) . . . . ?
C16 C17 C18 C19 -179.0(5) . . . . ?
C17 C18 C19 C20 1.6(9) . . . . ?
C18 C19 C20 C21 -2.6(9) . . . . ?
C19 C20 C21 C22 0.8(10) . . . . ?
C20 C21 C22 C17 1.9(9) . . . . ?
C18 C17 C22 C21 -2.8(7) . . . . ?
C16 C17 C22 C21 177.3(5) . . . . ?
C24 N1 C23 O3 14.1(12) . . . . ?
C28 N1 C23 O3 -146.5(12) . . . . ?
C27 N1 C23 O3 162.9(8) . . . . ?
C30 N1 C23 O3 -27.9(11) . . . . ?
C24 N1 C23 C16 -163.0(8) . . . . ?
C28 N1 C23 C16 36.4(15) . . . . ?
C27 N1 C23 C16 -14.2(12) . . . . ?
C30 N1 C23 C16 154.9(8) . . . . ?
O2 C16 C23 O3 -108.2(5) . . . . ?
C17 C16 C23 O3 67.0(6) . . . . ?
O2 C16 C23 N1 69.2(8) . . . . ?
C17 C16 C23 N1 -115.6(6) . . . . ?
C23 N1 C24 C25 -147.2(12) . . . . ?
C28 N1 C24 C25 15.2(18) . . . . ?
C27 N1 C24 C25 61.0(15) . . . . ?
C30 N1 C24 C25 -53.5(11) . . . . ?
C31 O4 C25 C24 36.4(18) . . . . ?
C26 O4 C25 C24 74.6(15) . . . . ?
C29 O4 C25 C24 -36.1(10) . . . . ?
N1 C24 C25 O4 -66.5(17) . . . . ?
C25 O4 C26 C27 -70.7(13) . . . . ?
C31 O4 C26 C27 32.7(12) . . . . ?
C29 O4 C26 C27 -31.2(16) . . . . ?
C23 N1 C27 C26 148.2(11) . . . . ?
C24 N1 C27 C26 -61.3(14) . . . . ?
C28 N1 C27 C26 41.4(11) . . . . ?
C30 N1 C27 C26 -20.1(16) . . . . ?
O4 C26 C27 N1 59.6(14) . . . . ?
C23 N1 C28 C31 -142.2(12) . . . . ?
C24 N1 C28 C31 56.5(18) . . . . ?
C27 N1 C28 C31 -39.9(9) . . . . ?
C30 N1 C28 C31 91.6(15) . . . . ?
C25 O4 C29 C30 37.6(10) . . . . ?
C31 O4 C29 C30 -79.9(18) . . . . ?
C26 O4 C29 C30 -48(2) . . . . ?
O4 C29 C30 N1 77.3(16) . . . . ?
C23 N1 C30 C29 140.1(14) . . . . ?
C24 N1 C30 C29 34.4(8) . . . . ?
C28 N1 C30 C29 -87.1(16) . . . . ?
C27 N1 C30 C29 -50.8(18) . . . . ?
C25 O4 C31 C28 43.2(19) . . . . ?
C26 O4 C31 C28 -47.5(12) . . . . ?
C29 O4 C31 C28 78.8(15) . . . . ?
N1 C28 C31 O4 -85.4(17) . . . . ?
