#------------------------------------------------------------------------------
#$Date: 2015-09-24 14:30:16 +0300 (Thu, 24 Sep 2015) $
#$Revision: 158281 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/78/7117841.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_7117841
loop_
_publ_author_name
'Ping Li'
'Josef M. Maier'
'Jungwun Hwang'
'Mark D. Smith'
'Jeanette A. Krause'
'Brian T. Mullis'
'Sharon M. S. Strickland'
'Ken D. Shimizu'
_publ_section_title
;
 Solvent-induced reversible solid-state colour change of an intramolecular
 charge-transfer complex
;
_journal_name_full               Chem.Commun.
_journal_page_first              14809
_journal_paper_doi               10.1039/C5cc06140G
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety
'C72 H54 N2 O8, 1.36(C2 H3 N), 0.64(C H2 Cl2)'
_chemical_formula_sum            'C75.36 H59.36 Cl1.28 N3.36 O8'
_chemical_formula_weight         1185.35
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2013.11.13 svn.r2834 for OlexSys, GUI svn.r4705)
;
_audit_update_record
;
2015-07-12 deposited with the CCDC.
2015-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.969(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.132(3)
_cell_length_b                   10.4771(16)
_cell_length_c                   17.718(3)
_cell_measurement_reflns_used    7671
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.878
_cell_measurement_theta_min      2.316
_cell_volume                     2906.0(8)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.631 (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            32604
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.116
_diffrn_reflns_theta_min         2.146
_diffrn_source                   'sealed tube'
_diffrn_source_current           37.0
_diffrn_source_power             1.739
_diffrn_source_voltage           47.0
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             1242
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         5169
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0846
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1244P)²+4.4388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2333
_refine_ls_wR_factor_ref         0.2507
_reflns_number_gt                3840
_reflns_number_total             5169
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc06140g2.cif.txt
_cod_data_source_block           dfya53m
_cod_database_code               7117841
_shelxl_version_number           2013-4
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C32A, C32B}
3. Restrained distances
 N1S-C1S
 1.13 with sigma of 0.02
 C1S-C2S
 1.445 with sigma of 0.02
 C3S-Cl1S = C3S-Cl2S
 1.76 with sigma of 0.02
 Cl1S-Cl2S
 2.93 with sigma of 0.02
 C4S-Cl3S = C4S-Cl4S
 1.76 with sigma of 0.02
 Cl3S-Cl4S
 2.93 with sigma of 0.02
 N1S-C2S
 0.02 with sigma of 2.57
 C32A-C33A \\sim C32A-C34A \\sim C32A-C35A \\sim C32B-C33B \\sim C32B-C34B
\\sim C32B-C35B
 with sigma of 0.01
 C33A-C34A \\sim C34A-C35A \\sim C35A-C33A \\sim C33B-C34B \\sim C34B-C35B
\\sim C35B-C33B
 with sigma of 0.02
 C35A-C36A \\sim C35B-C36B
 with sigma of 0.01
 C32A-C36A \\sim C32B-C36B
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C32A) = Uanis(C32B)
Uiso(C33A) = Uiso(C33B)
Uiso(C2S) = Uiso(C3S) = Uiso(C4S)
5. Rigid body (RIGU) restrains
 C20, C26, C27, C28, C29, C30, C21, C19, C31
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 1*[Sof(N1S)+Sof(C1S)+Sof(C2S)+Sof(H2SA)+Sof(H2SB)+Sof(H2SC)]+1*[Sof(C3S)+
 Sof(H3SA)+Sof(H3SB)+Sof(Cl1S)+Sof(Cl2S)]+1*[Sof(C4S)+Sof(H4SA)+Sof(H4SB)+
 Sof(Cl3S)+Sof(Cl4S)]=1 with esd of 0.0001
 Sof(C32B)=Sof(C33B)=Sof(H33D)=Sof(H33E)=Sof(H33F)=Sof(C34B)=Sof(H34D)=
 Sof(H34E)=Sof(H34F)=Sof(C35B)=Sof(H35C)=Sof(H35D)=Sof(C36B)=Sof(H36D)=
 Sof(H36E)=Sof(H36F)=1-FVAR(1)
 Sof(C32A)=Sof(C33A)=Sof(H33A)=Sof(H33B)=Sof(H33C)=Sof(C34A)=Sof(H34A)=
 Sof(H34B)=Sof(H34C)=Sof(C35A)=Sof(H35A)=Sof(H35B)=Sof(C36A)=Sof(H36A)=
 Sof(H36B)=Sof(H36C)=FVAR(1)
 Sof(N1S)=Sof(C1S)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(H2SC)=FVAR(2)
 Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(Cl1S)=Sof(Cl2S)=FVAR(3)
 Sof(C4S)=Sof(H4SA)=Sof(H4SB)=Sof(Cl3S)=Sof(Cl4S)=FVAR(4)
7.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C35A(H35A,H35B), C35B(H35C,H35D), C3S(H3SA,H3SB), C4S(H4SA,
 H4SB)
7.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C18(H18), C19(H19), C24(H24),
 C25(H25), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31)
7.c Idealised Me refined with riding coordinates:
 C33A(H33A,H33B,H33C), C34A(H34A,H34B,H34C), C36A(H36A,H36B,H36C), C33B(H33D,
 H33E,H33F), C34B(H34D,H34E,H34F), C36B(H36D,H36E,H36F), C2S(H2SA,H2SB,H2SC)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.23641(14) 0.4296(2) 0.40043(14) 0.0375(6) Uani 1 1 d . . . . .
O2 O 0.39664(15) 0.4562(3) 0.67610(14) 0.0451(7) Uani 1 1 d . . . . .
O3 O 0.20289(15) 0.6333(2) 0.51907(16) 0.0417(6) Uani 1 1 d . . . . .
O4 O 0.08992(16) 0.6237(3) 0.39574(19) 0.0543(8) Uani 1 1 d . . . . .
N1 N 0.31747(16) 0.4399(2) 0.53822(16) 0.0286(6) Uani 1 1 d . . . . .
C1 C 0.30645(19) 0.4446(3) 0.45540(19) 0.0278(7) Uani 1 1 d . . . . .
C2 C 0.38458(19) 0.4676(3) 0.44073(18) 0.0255(7) Uani 1 1 d . . . . .
C3 C 0.46342(18) 0.4891(3) 0.50787(18) 0.0231(6) Uani 1 1 d . . . . .
C4 C 0.47047(19) 0.4892(3) 0.59008(19) 0.0269(7) Uani 1 1 d . . . . .
C5 C 0.3947(2) 0.4616(3) 0.6073(2) 0.0302(7) Uani 1 1 d . . . . .
C6 C 0.3793(2) 0.4666(3) 0.36104(19) 0.0288(7) Uani 1 1 d . . . . .
H6 H 0.3259 0.4514 0.3162 0.035 Uiso 1 1 calc R . . . .
C7 C 0.5479(2) 0.5122(3) 0.65425(19) 0.0302(7) Uani 1 1 d . . . . .
H7 H 0.5520 0.5137 0.7094 0.036 Uiso 1 1 calc R . . . .
C8 C 0.2425(2) 0.4172(3) 0.5543(2) 0.0316(7) Uani 1 1 d . . . . .
C9 C 0.1847(2) 0.5134(3) 0.5429(2) 0.0343(8) Uani 1 1 d . . . . .
C10 C 0.1144(2) 0.4941(4) 0.5608(2) 0.0402(8) Uani 1 1 d . . . . .
H10 H 0.0737 0.5603 0.5517 0.048 Uiso 1 1 calc R . . . .
C11 C 0.1036(2) 0.3776(4) 0.5919(2) 0.0419(9) Uani 1 1 d . . . . .
H11 H 0.0557 0.3656 0.6053 0.050 Uiso 1 1 calc R . . . .
C12 C 0.1610(2) 0.2772(4) 0.6042(2) 0.0445(9) Uani 1 1 d . . . . .
C13 C 0.2308(2) 0.3003(3) 0.5845(2) 0.0390(8) Uani 1 1 d . . . . .
H13 H 0.2712 0.2341 0.5920 0.047 Uiso 1 1 calc R . . . .
C14 C 0.1507(2) 0.6797(4) 0.4430(3) 0.0464(10) Uani 1 1 d . . . . .
C15 C 0.1818(2) 0.8088(4) 0.4305(3) 0.0577(12) Uani 1 1 d . . . . .
H15A H 0.1889 0.8636 0.4783 0.069 Uiso 1 1 calc R . . . .
H15B H 0.1378 0.8485 0.3807 0.069 Uiso 1 1 calc R . . . .
C16 C 0.2659(2) 0.8050(3) 0.4205(2) 0.0425(9) Uani 1 1 d . . . . .
C17 C 0.3458(2) 0.8158(3) 0.4879(2) 0.0362(8) Uani 1 1 d . . . . .
C18 C 0.3565(3) 0.8241(4) 0.5717(3) 0.0522(10) Uani 1 1 d . . . . .
H18 H 0.3081 0.8180 0.5848 0.063 Uiso 1 1 calc R . . . .
C19 C 0.4360(4) 0.8409(4) 0.6337(3) 0.0688(13) Uani 1 1 d . . . . .
H19 H 0.4414 0.8476 0.6890 0.083 Uiso 1 1 calc R . . . .
C20 C 0.5109(3) 0.8485(4) 0.6174(4) 0.0708(13) Uani 1 1 d . . . . .
C21 C 0.5016(2) 0.8383(3) 0.5361(3) 0.0601(12) Uani 1 1 d . . . . .
C22 C 0.4204(2) 0.8209(3) 0.4715(3) 0.0422(9) Uani 1 1 d . . . . .
C23 C 0.4132(3) 0.8117(3) 0.3890(3) 0.0529(11) Uani 1 1 d . . . . .
C24 C 0.3321(3) 0.7986(4) 0.3250(3) 0.0585(11) Uani 1 1 d . . . . .
H24 H 0.3267 0.7910 0.2696 0.070 Uiso 1 1 calc R . . . .
C25 C 0.2614(3) 0.7966(4) 0.3410(3) 0.0524(10) Uani 1 1 d . . . . .
H25 H 0.2070 0.7892 0.2963 0.063 Uiso 1 1 calc R . . . .
C26 C 0.5920(4) 0.8698(5) 0.6800(5) 0.106(2) Uani 1 1 d . . . . .
H26 H 0.6005 0.8776 0.7362 0.127 Uiso 1 1 calc R . . . .
C27 C 0.6629(4) 0.8796(5) 0.6547(6) 0.107(2) Uani 1 1 d . . . . .
H27 H 0.7185 0.8941 0.6962 0.129 Uiso 1 1 calc R . . . .
C28 C 0.6540(3) 0.8692(5) 0.5754(6) 0.104(2) Uani 1 1 d . . . . .
H28 H 0.7028 0.8760 0.5629 0.125 Uiso 1 1 calc R . . . .
C29 C 0.5760(3) 0.8492(4) 0.5137(4) 0.0774(14) Uani 1 1 d . . . . .
C30 C 0.5614(4) 0.8401(4) 0.4289(5) 0.0860(16) Uani 1 1 d . . . . .
H30 H 0.6089 0.8473 0.4144 0.103 Uiso 1 1 calc R . . . .
C31 C 0.4878(4) 0.8229(4) 0.3718(4) 0.0789(15) Uani 1 1 d . . . . .
H31 H 0.4819 0.8173 0.3163 0.095 Uiso 1 1 calc R . . . .
C32A C 0.1523(2) 0.1492(4) 0.6419(3) 0.0674(14) Uani 0.565(9) 1 d . . P A 1
C33A C 0.0694(4) 0.1382(9) 0.6535(6) 0.0562(16) Uiso 0.565(9) 1 d . . P A 1
H33A H 0.0667 0.2064 0.6902 0.084 Uiso 0.565(9) 1 calc R . P A 1
H33B H 0.0673 0.0551 0.6780 0.084 Uiso 0.565(9) 1 calc R . P A 1
H33C H 0.0209 0.1459 0.5998 0.084 Uiso 0.565(9) 1 calc R . P A 1
C34A C 0.1497(6) 0.0408(8) 0.5782(5) 0.069(3) Uiso 0.565(9) 1 d . . P A 1
H34A H 0.1010 0.0554 0.5254 0.103 Uiso 0.565(9) 1 calc R . P A 1
H34B H 0.1437 -0.0427 0.6002 0.103 Uiso 0.565(9) 1 calc R . P A 1
H34C H 0.2027 0.0428 0.5697 0.103 Uiso 0.565(9) 1 calc R . P A 1
C35A C 0.2296(5) 0.1114(8) 0.7182(4) 0.066(3) Uiso 0.565(9) 1 d . . P A 1
H35A H 0.2222 0.0258 0.7381 0.079 Uiso 0.565(9) 1 calc R . P A 1
H35B H 0.2821 0.1118 0.7077 0.079 Uiso 0.565(9) 1 calc R . P A 1
C36A C 0.2325(7) 0.2132(10) 0.7786(6) 0.084(3) Uiso 0.565(9) 1 d . . P A 1
H36A H 0.2029 0.2896 0.7486 0.126 Uiso 0.565(9) 1 calc R . P A 1
H36B H 0.2921 0.2344 0.8134 0.126 Uiso 0.565(9) 1 calc R . P A 1
H36C H 0.2042 0.1824 0.8134 0.126 Uiso 0.565(9) 1 calc R . P A 1
C32B C 0.1523(2) 0.1492(4) 0.6419(3) 0.0674(14) Uani 0.435(9) 1 d . . P A 2
C33B C 0.0612(4) 0.1170(12) 0.6299(7) 0.0562(16) Uiso 0.435(9) 1 d . . P A 2
H33D H 0.0397 0.1835 0.6554 0.084 Uiso 0.435(9) 1 calc R . P A 2
H33E H 0.0607 0.0346 0.6559 0.084 Uiso 0.435(9) 1 calc R . P A 2
H33F H 0.0246 0.1122 0.5708 0.084 Uiso 0.435(9) 1 calc R . P A 2
C34B C 0.1977(8) 0.0380(10) 0.6253(8) 0.080(4) Uiso 0.435(9) 1 d . . P A 2
H34D H 0.1756 0.0230 0.5656 0.120 Uiso 0.435(9) 1 calc R . P A 2
H34E H 0.1882 -0.0381 0.6526 0.120 Uiso 0.435(9) 1 calc R . P A 2
H34F H 0.2590 0.0562 0.6467 0.120 Uiso 0.435(9) 1 calc R . P A 2
C35B C 0.2000(7) 0.1713(14) 0.7378(5) 0.087(4) Uiso 0.435(9) 1 d . . P A 2
H35C H 0.1756 0.2471 0.7538 0.104 Uiso 0.435(9) 1 calc R . P A 2
H35D H 0.1910 0.0964 0.7674 0.104 Uiso 0.435(9) 1 calc R . P A 2
C36B C 0.2938(8) 0.1908(19) 0.7626(10) 0.124(7) Uiso 0.435(9) 1 d . . P A 2
H36D H 0.3051 0.2030 0.7131 0.186 Uiso 0.435(9) 1 calc R . P A 2
H36E H 0.3251 0.1158 0.7930 0.186 Uiso 0.435(9) 1 calc R . P A 2
H36F H 0.3126 0.2665 0.7980 0.186 Uiso 0.435(9) 1 calc R . P A 2
N1S N 0.3730(4) 0.6070(7) 0.1422(4) 0.058(2) Uiso 0.680(3) 1 d D . P B 1
C1S C 0.4083(4) 0.6929(7) 0.1428(4) 0.0459(17) Uiso 0.680(3) 1 d D . P B 1
C2S C 0.4518(5) 0.8088(8) 0.1382(5) 0.0595(16) Uiso 0.680(3) 1 d D . P B 1
H2SA H 0.4096 0.8747 0.1093 0.089 Uiso 0.680(3) 1 calc R . P B 1
H2SB H 0.4876 0.7922 0.1081 0.089 Uiso 0.680(3) 1 calc R . P B 1
H2SC H 0.4876 0.8383 0.1942 0.089 Uiso 0.680(3) 1 calc R . P B 1
C3S C 0.4339(10) 0.7803(19) 0.1175(14) 0.0595(16) Uiso 0.242(3) 1 d D . P C 2
H3SA H 0.4259 0.7794 0.0590 0.071 Uiso 0.242(3) 1 calc R . P C 2
H3SB H 0.4066 0.8584 0.1270 0.071 Uiso 0.242(3) 1 calc R . P C 2
Cl1S Cl 0.3857(4) 0.6466(7) 0.1378(3) 0.0548(14) Uiso 0.242(3) 1 d D . P C 2
Cl2S Cl 0.5411(3) 0.7822(5) 0.1803(3) 0.0727(16) Uiso 0.242(3) 1 d D . P C 2
C4S C 0.453(2) 0.784(8) 0.127(4) 0.0595(16) Uiso 0.078(2) 1 d D . P D 3
H4SA H 0.4213 0.7212 0.1449 0.071 Uiso 0.078(2) 1 calc R . P D 3
H4SB H 0.4117 0.8416 0.0858 0.071 Uiso 0.078(2) 1 calc R . P D 3
Cl3S Cl 0.5129(10) 0.7040(15) 0.0813(9) 0.070(5) Uiso 0.078(2) 1 d D . P D 3
Cl4S Cl 0.5229(13) 0.8729(18) 0.2123(11) 0.086(6) Uiso 0.078(2) 1 d D . P D 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C14 O3 C9 118.6(3) . .
C1 N1 C5 125.7(2) . .
C1 N1 C8 117.4(3) . .
C5 N1 C8 116.9(2) . .
O1 C1 N1 120.4(3) . .
O1 C1 C2 123.4(3) . .
N1 C1 C2 116.2(3) . .
C3 C2 C1 120.1(3) . .
C6 C2 C1 119.4(3) . .
C6 C2 C3 120.5(3) . .
C2 C3 C3 118.9(3) . 3_666
C2 C3 C4 121.5(3) . .
C3 C3 C4 119.6(3) 3_666 .
C3 C4 C5 119.9(3) . .
C7 C4 C3 120.2(3) . .
C7 C4 C5 119.9(3) . .
O2 C5 N1 120.0(3) . .
O2 C5 C4 123.4(3) . .
N1 C5 C4 116.5(3) . .
C2 C6 H6 119.8 . .
C2 C6 C7 120.4(3) . 3_666
C7 C6 H6 119.8 3_666 .
C4 C7 C6 120.4(3) . 3_666
C4 C7 H7 119.8 . .
C6 C7 H7 119.8 3_666 .
C9 C8 N1 119.8(3) . .
C9 C8 C13 119.9(3) . .
C13 C8 N1 120.2(3) . .
C8 C9 O3 117.9(3) . .
C8 C9 C10 120.4(3) . .
C10 C9 O3 121.5(3) . .
C9 C10 H10 120.3 . .
C9 C10 C11 119.5(3) . .
C11 C10 H10 120.3 . .
C10 C11 H11 119.1 . .
C10 C11 C12 121.9(3) . .
C12 C11 H11 119.1 . .
C11 C12 C13 116.8(3) . .
C11 C12 C32A 122.8(3) . .
C13 C12 C32A 120.3(3) . .
C8 C13 C12 121.6(3) . .
C8 C13 H13 119.2 . .
C12 C13 H13 119.2 . .
O3 C14 C15 109.7(3) . .
O4 C14 O3 123.5(3) . .
O4 C14 C15 126.8(4) . .
C14 C15 H15A 108.8 . .
C14 C15 H15B 108.8 . .
C14 C15 C16 113.8(3) . .
H15A C15 H15B 107.7 . .
C16 C15 H15A 108.8 . .
C16 C15 H15B 108.8 . .
C17 C16 C15 122.6(4) . .
C25 C16 C15 117.1(4) . .
C25 C16 C17 120.2(3) . .
C16 C17 C18 124.0(3) . .
C16 C17 C22 118.3(3) . .
C22 C17 C18 117.7(3) . .
C17 C18 H18 119.7 . .
C19 C18 C17 120.6(4) . .
C19 C18 H18 119.7 . .
C18 C19 H19 119.0 . .
C18 C19 C20 121.9(5) . .
C20 C19 H19 119.0 . .
C21 C20 C19 118.1(4) . .
C21 C20 C26 119.5(6) . .
C26 C20 C19 122.3(6) . .
C20 C21 C22 120.8(4) . .
C20 C21 C29 121.5(4) . .
C22 C21 C29 117.6(5) . .
C21 C22 C17 120.8(4) . .
C21 C22 C23 119.3(4) . .
C23 C22 C17 119.9(3) . .
C22 C23 C31 120.1(5) . .
C24 C23 C22 118.9(4) . .
C24 C23 C31 120.9(5) . .
C23 C24 H24 119.6 . .
C25 C24 C23 120.7(4) . .
C25 C24 H24 119.6 . .
C16 C25 H25 119.0 . .
C24 C25 C16 121.9(4) . .
C24 C25 H25 119.0 . .
C20 C26 H26 121.6 . .
C20 C26 C27 116.8(7) . .
C27 C26 H26 121.6 . .
C26 C27 H27 118.1 . .
C28 C27 C26 123.8(6) . .
C28 C27 H27 118.1 . .
C27 C28 H28 119.8 . .
C27 C28 C29 120.4(7) . .
C29 C28 H28 119.8 . .
C28 C29 C21 117.9(7) . .
C28 C29 C30 123.6(6) . .
C30 C29 C21 118.5(4) . .
C29 C30 H30 118.6 . .
C31 C30 C29 122.8(5) . .
C31 C30 H30 118.6 . .
C23 C31 H31 119.1 . .
C30 C31 C23 121.7(6) . .
C30 C31 H31 119.1 . .
C12 C32A C34A 107.3(4) . .
C33A C32A C12 112.7(5) . .
C33A C32A C34A 106.5(5) . .
C35A C32A C12 114.5(5) . .
C35A C32A C33A 112.7(5) . .
C35A C32A C34A 102.1(5) . .
C32A C33A H33A 109.5 . .
C32A C33A H33B 109.5 . .
C32A C33A H33C 109.5 . .
H33A C33A H33B 109.5 . .
H33A C33A H33C 109.5 . .
H33B C33A H33C 109.5 . .
C32A C34A H34A 109.5 . .
C32A C34A H34B 109.5 . .
C32A C34A H34C 109.5 . .
H34A C34A H34B 109.5 . .
H34A C34A H34C 109.5 . .
H34B C34A H34C 109.5 . .
C32A C35A H35A 111.3 . .
C32A C35A H35B 111.3 . .
H35A C35A H35B 109.2 . .
C36A C35A C32A 102.4(6) . .
C36A C35A H35A 111.3 . .
C36A C35A H35B 111.3 . .
C35A C36A H36A 109.5 . .
C35A C36A H36B 109.5 . .
C35A C36A H36C 109.5 . .
H36A C36A H36B 109.5 . .
H36A C36A H36C 109.5 . .
H36B C36A H36C 109.5 . .
H33D C33B H33E 109.5 . .
H33D C33B H33F 109.5 . .
H33E C33B H33F 109.5 . .
H34D C34B H34E 109.5 . .
H34D C34B H34F 109.5 . .
H34E C34B H34F 109.5 . .
H35C C35B H35D 108.0 . .
C36B C35B H35C 109.4 . .
C36B C35B H35D 109.4 . .
C35B C36B H36D 109.5 . .
C35B C36B H36E 109.5 . .
C35B C36B H36F 109.5 . .
H36D C36B H36E 109.5 . .
H36D C36B H36F 109.5 . .
H36E C36B H36F 109.5 . .
N1S C1S C2S 176.3(7) . .
C1S C2S H2SA 109.5 . .
C1S C2S H2SB 109.5 . .
C1S C2S H2SC 109.5 . .
H2SA C2S H2SB 109.5 . .
H2SA C2S H2SC 109.5 . .
H2SB C2S H2SC 109.5 . .
H3SA C3S H3SB 108.1 . .
Cl1S C3S H3SA 109.6 . .
Cl1S C3S H3SB 109.6 . .
Cl2S C3S H3SA 109.6 . .
Cl2S C3S H3SB 109.6 . .
Cl2S C3S Cl1S 110.4(11) . .
H4SA C4S H4SB 108.2 . .
Cl3S C4S H4SA 109.8 . .
Cl3S C4S H4SB 109.8 . .
Cl3S C4S Cl4S 109.4(16) . .
Cl4S C4S H4SA 109.8 . .
Cl4S C4S H4SB 109.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.210(4) .
O2 C5 1.208(4) .
O3 C9 1.401(4) .
O3 C14 1.368(5) .
O4 C14 1.193(5) .
N1 C1 1.402(4) .
N1 C5 1.408(4) .
N1 C8 1.444(4) .
C1 C2 1.483(4) .
C2 C3 1.409(4) .
C2 C6 1.378(4) .
C3 C3 1.409(6) 3_666
C3 C4 1.412(4) .
C4 C5 1.478(4) .
C4 C7 1.373(4) .
C6 H6 0.9500 .
C6 C7 1.397(4) 3_666
C7 C6 1.397(4) 3_666
C7 H7 0.9500 .
C8 C9 1.370(5) .
C8 C13 1.383(5) .
C9 C10 1.379(5) .
C10 H10 0.9500 .
C10 C11 1.383(5) .
C11 H11 0.9500 .
C11 C12 1.395(5) .
C12 C13 1.397(5) .
C12 C32A 1.531(5) .
C13 H13 0.9500 .
C14 C15 1.503(5) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C15 C16 1.522(5) .
C16 C17 1.408(5) .
C16 C25 1.381(6) .
C17 C18 1.423(6) .
C17 C22 1.422(5) .
C18 H18 0.9500 .
C18 C19 1.369(6) .
C19 H19 0.9500 .
C19 C20 1.428(8) .
C20 C21 1.387(8) .
C20 C26 1.399(7) .
C21 C22 1.410(5) .
C21 C29 1.485(7) .
C22 C23 1.420(6) .
C23 C24 1.398(6) .
C23 C31 1.433(6) .
C24 H24 0.9500 .
C24 C25 1.353(6) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C26 C27 1.459(11) .
C27 H27 0.9500 .
C27 C28 1.354(11) .
C28 H28 0.9500 .
C28 C29 1.357(8) .
C29 C30 1.422(9) .
C30 H30 0.9500 .
C30 C31 1.269(9) .
C31 H31 0.9500 .
C32A C33A 1.520(6) .
C32A C34A 1.589(6) .
C32A C35A 1.512(6) .
C33A H33A 0.9800 .
C33A H33B 0.9800 .
C33A H33C 0.9800 .
C34A H34A 0.9800 .
C34A H34B 0.9800 .
C34A H34C 0.9800 .
C35A H35A 0.9900 .
C35A H35B 0.9900 .
C35A C36A 1.498(10) .
C36A H36A 0.9800 .
C36A H36B 0.9800 .
C36A H36C 0.9800 .
C33B H33D 0.9800 .
C33B H33E 0.9800 .
C33B H33F 0.9800 .
C34B H34D 0.9800 .
C34B H34E 0.9800 .
C34B H34F 0.9800 .
C35B H35C 0.9900 .
C35B H35D 0.9900 .
C35B C36B 1.499(11) .
C36B H36D 0.9800 .
C36B H36E 0.9800 .
C36B H36F 0.9800 .
N1S C1S 1.083(9) .
C1S C2S 1.444(10) .
C2S H2SA 0.9800 .
C2S H2SB 0.9800 .
C2S H2SC 0.9800 .
C3S H3SA 0.9900 .
C3S H3SB 0.9900 .
C3S Cl1S 1.736(17) .
C3S Cl2S 1.717(15) .
C4S H4SA 0.9900 .
C4S H4SB 0.9900 .
C4S Cl3S 1.75(2) .
C4S Cl4S 1.77(2) .
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
O1 C1 C2 C3 177.6(3) . . . .
O1 C1 C2 C6 -2.9(4) . . . .
O3 C9 C10 C11 -173.6(3) . . . .
O3 C14 C15 C16 69.5(5) . . . .
O4 C14 C15 C16 -110.9(5) . . . .
N1 C1 C2 C3 -2.9(4) . . . .
N1 C1 C2 C6 176.6(3) . . . .
N1 C8 C9 O3 -2.7(5) . . . .
N1 C8 C9 C10 -177.8(3) . . . .
N1 C8 C13 C12 177.0(3) . . . .
C1 N1 C5 O2 179.3(3) . . . .
C1 N1 C5 C4 -1.2(4) . . . .
C1 N1 C8 C9 -75.7(4) . . . .
C1 N1 C8 C13 107.1(4) . . . .
C1 C2 C3 C3 -179.9(3) . . . 3_666
C1 C2 C3 C4 0.1(4) . . . .
C1 C2 C6 C7 -179.9(3) . . . 3_666
C2 C3 C4 C5 2.3(4) . . . .
C2 C3 C4 C7 -179.1(3) . . . .
C3 C2 C6 C7 -0.4(4) . . . 3_666
C3 C3 C4 C5 -177.7(3) 3_666 . . .
C3 C3 C4 C7 0.9(5) 3_666 . . .
C3 C4 C5 O2 177.6(3) . . . .
C3 C4 C5 N1 -1.8(4) . . . .
C3 C4 C7 C6 -1.1(5) . . . 3_666
C5 N1 C1 O1 -177.0(3) . . . .
C5 N1 C1 C2 3.5(4) . . . .
C5 N1 C8 C9 101.4(4) . . . .
C5 N1 C8 C13 -75.9(4) . . . .
C5 C4 C7 C6 177.5(3) . . . 3_666
C6 C2 C3 C3 0.7(5) . . . 3_666
C6 C2 C3 C4 -179.3(3) . . . .
C7 C4 C5 O2 -1.0(5) . . . .
C7 C4 C5 N1 179.6(3) . . . .
C8 N1 C1 O1 -0.2(4) . . . .
C8 N1 C1 C2 -179.7(3) . . . .
C8 N1 C5 O2 2.6(4) . . . .
C8 N1 C5 C4 -178.0(3) . . . .
C8 C9 C10 C11 1.3(5) . . . .
C9 O3 C14 O4 0.4(5) . . . .
C9 O3 C14 C15 180.0(3) . . . .
C9 C8 C13 C12 -0.2(5) . . . .
C9 C10 C11 C12 -1.5(6) . . . .
C10 C11 C12 C13 0.8(6) . . . .
C10 C11 C12 C32A 177.5(4) . . . .
C11 C12 C13 C8 0.1(6) . . . .
C11 C12 C32A C33A 7.4(7) . . . .
C11 C12 C32A C34A 124.3(5) . . . .
C11 C12 C32A C35A -123.2(5) . . . .
C12 C32A C35A C36A 64.5(7) . . . .
C13 C8 C9 O3 174.6(3) . . . .
C13 C8 C9 C10 -0.5(5) . . . .
C13 C12 C32A C33A -175.9(5) . . . .
C13 C12 C32A C34A -59.1(6) . . . .
C13 C12 C32A C35A 53.5(6) . . . .
C14 O3 C9 C8 114.9(4) . . . .
C14 O3 C9 C10 -70.1(4) . . . .
C14 C15 C16 C17 -90.7(5) . . . .
C14 C15 C16 C25 92.3(4) . . . .
C15 C16 C17 C18 3.6(5) . . . .
C15 C16 C17 C22 -175.3(3) . . . .
C15 C16 C25 C24 176.9(4) . . . .
C16 C17 C18 C19 -176.7(4) . . . .
C16 C17 C22 C21 176.7(3) . . . .
C16 C17 C22 C23 -1.7(5) . . . .
C17 C16 C25 C24 -0.1(6) . . . .
C17 C18 C19 C20 -1.1(6) . . . .
C17 C22 C23 C24 0.5(5) . . . .
C17 C22 C23 C31 177.0(3) . . . .
C18 C17 C22 C21 -2.3(5) . . . .
C18 C17 C22 C23 179.4(3) . . . .
C18 C19 C20 C21 0.0(6) . . . .
C18 C19 C20 C26 177.8(4) . . . .
C19 C20 C21 C22 -0.1(6) . . . .
C19 C20 C21 C29 178.1(3) . . . .
C19 C20 C26 C27 -178.1(4) . . . .
C20 C21 C22 C17 1.3(5) . . . .
C20 C21 C22 C23 179.6(3) . . . .
C20 C21 C29 C28 0.1(6) . . . .
C20 C21 C29 C30 -178.9(4) . . . .
C20 C26 C27 C28 0.0(8) . . . .
C21 C20 C26 C27 -0.3(6) . . . .
C21 C22 C23 C24 -177.9(3) . . . .
C21 C22 C23 C31 -1.4(5) . . . .
C21 C29 C30 C31 -0.2(7) . . . .
C22 C17 C18 C19 2.2(5) . . . .
C22 C21 C29 C28 178.4(4) . . . .
C22 C21 C29 C30 -0.6(5) . . . .
C22 C23 C24 C25 1.0(6) . . . .
C22 C23 C31 C30 0.6(6) . . . .
C23 C24 C25 C16 -1.2(6) . . . .
C24 C23 C31 C30 177.0(4) . . . .
C25 C16 C17 C18 -179.6(3) . . . .
C25 C16 C17 C22 1.5(5) . . . .
C26 C20 C21 C22 -178.0(4) . . . .
C26 C20 C21 C29 0.2(6) . . . .
C26 C27 C28 C29 0.4(8) . . . .
C27 C28 C29 C21 -0.4(7) . . . .
C27 C28 C29 C30 178.5(5) . . . .
C28 C29 C30 C31 -179.1(4) . . . .
C29 C21 C22 C17 -177.0(3) . . . .
C29 C21 C22 C23 1.4(5) . . . .
C29 C30 C31 C23 0.2(7) . . . .
C31 C23 C24 C25 -175.5(4) . . . .
C32A C12 C13 C8 -176.8(4) . . . .
C33A C32A C35A C36A -66.1(8) . . . .
C34A C32A C35A C36A -179.9(7) . . . .
