#------------------------------------------------------------------------------
#$Date: 2017-02-04 08:26:01 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191449 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/96/7119608.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_7119608
loop_
_publ_author_name
'Fan, Wei'
'Liu, Chunming'
'Li, Yan'
'Wang, Zhaohui'
_publ_section_title
;
 Fluoroalkyl-modified naphthodithiophene diimides.
;
_journal_issue                   1
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              188
_journal_page_last               191
_journal_paper_doi               10.1039/c6cc07102c
_journal_volume                  53
_journal_year                    2016
_chemical_formula_moiety         'C42 H38 N2 O4 S2, 0.76(C H2 Cl2)'
_chemical_formula_sum            'C42.77 H39.54 Cl1.54 N2 O4 S2'
_chemical_formula_weight         764.25
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-11-15
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_audit_update_record
;
2016-11-15 deposited with the CCDC.
2016-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                97.10(3)
_cell_angle_beta                 101.59(3)
_cell_angle_gamma                107.30(3)
_cell_formula_units_Z            1
_cell_length_a                   8.9017(18)
_cell_length_b                   9.2639(19)
_cell_length_c                   13.141(3)
_cell_measurement_reflns_used    3095
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4809
_cell_measurement_theta_min      1.6133
_cell_volume                     993.9(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
scan:
    Number of images: 358
               Slice: -110.0000 - 69.0000
         Image width: 0.5000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 40.2277
              2theta: -20.2509
scan:
    Number of images: 348
               Slice: -110.0000 - 64.0000
         Image width: 0.5000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 40.2277
              2theta: -20.2509
scan:
    Number of images: 240
               Slice: -110.0000 - 10.0000
         Image width: 0.5000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 40.2277
              2theta: -20.2509
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0158
_diffrn_orient_matrix_UB_12      -0.1185
_diffrn_orient_matrix_UB_13      0.0219
_diffrn_orient_matrix_UB_21      0.1098
_diffrn_orient_matrix_UB_22      -0.0285
_diffrn_orient_matrix_UB_23      -0.0209
_diffrn_orient_matrix_UB_31      0.0295
_diffrn_orient_matrix_UB_32      -0.0029
_diffrn_orient_matrix_UB_33      0.0735
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11646
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         1.613
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4518
_refine_ls_number_restraints     243
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0774
_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)+(0.1015P)²+0.5597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2008
_refine_ls_wR_factor_ref         0.2086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3924
_reflns_number_total             4518
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc07102c2.cif
_cod_data_source_block           mx3353
_cod_original_cell_volume        993.8(4)
_cod_database_code               7119608
_diffrn_number_total             4520
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H14 of C14, H13 of C13, H12 of C12, H2 of C2, H1 of C1, {H19A,H19} of C19,
  {H16,H16A} of C16, {H1AA,H1AB} of C1A, H1E of C1E, H2A of C2A
 At 1.5 times of:
  {H20A,H20B,H20C} of C20, {H18A,H18B,H18C} of C18, {H17A,H17B,H17C} of C17,
  {H20D,H20E,H20F} of C20A, {H21D,H21E,H21F} of C21A, {H18D,H18E,H18F} of C18A,
  {H17D,H17E,H17F} of C17A, {H21A,H21B,H21C} of C21
2. Restrained distances
 C18A-C16 = C17A-C16
 1.54 with sigma of 0.01
 S1A-C1E
 1.76 with sigma of 0.01
 C2A-C1E
 1.39 with sigma of 0.01
 Cl1D-C1A = Cl1B-C1A
 1.76 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C19 ~ C20 ~ C21 ~ C21A ~ C20A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
C17 ~ C18 ~ C17A ~ C18A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
S1 ~ C1 ~ C2 ~ C3 ~ C4 ~ S1A ~ C2A ~ C1E: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C21) ~ Ueq, Uanis(C21A) ~ Ueq, Uanis(C19) ~ Ueq, Uanis(C20A) ~ Ueq, Uanis(C20) ~ Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C17) ~ Ueq, Uanis(C17A) ~ Ueq, Uanis(C18) ~ Ueq, Uanis(C18A) ~ Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(S1) ~ Ueq, Uanis(C1) ~ Ueq, Uanis(C2) ~ Ueq, Uanis(C3) ~ Ueq, Uanis(C4) ~ Ueq, Uanis(S1A) ~ Ueq, Uanis(C2A) ~ Ueq, Uanis(C1E) ~ Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H16)=1-Sof(H16A)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C18)=
 Sof(H18A)=Sof(H18B)=Sof(H18C)=1-Sof(H16A)=1-Sof(H16A)=1-Sof(H16A)=1-Sof(H16A)=
 1-Sof(H16A)=1-Sof(H16A)=1-Sof(H16A)=1-Sof(H16A)
 1-Sof(H19)=Sof(H19)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C21)=Sof(H21A)=
 Sof(H21B)=Sof(H21C)=1-Sof(H19)=1-Sof(H19)=1-Sof(H19)=1-Sof(H19)=1-Sof(H19)=1-
 Sof(H19)=1-Sof(H19)=1-Sof(H19)
 Sof(S1)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=1-Sof(C1)=1-Sof(C1)=1-Sof(C1)=1-
 Sof(C1)=1-Sof(C1)
 Sof(Cl1B)=Sof(Cl1D)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)
5.a Riding coordinates:
 C18(H18A,H18B,H18C), C18A(H18D,H18E,H18F)
5.b Ternary CH refined with riding coordinates:
 C16(H16), C16(H16A), C19(H19A), C19(H19)
5.c Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C12(H12), C13(H13), C14(H14), C2A(H2A), C1E(H1E)
5.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C17A(H17D,H17E,
 H17F), C21A(H21D,H21E,H21F), C20A(H20D,H20E,H20F)
;
_olex2_submission_special_instructions 'No special instructions were received'
_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.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_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
S1 S 0.2565(2) 0.64982(19) 0.72529(11) 0.0365(3) Uani 0.758(4) 1 d . U P A 1
O1 O 0.5045(2) 0.8752(2) 0.68292(14) 0.0516(5) Uani 1 1 d . . . . .
O2 O 0.8562(3) 1.3160(2) 0.89655(15) 0.0605(6) Uani 1 1 d . . . . .
N1 N 0.6797(2) 1.0968(2) 0.79025(14) 0.0324(4) Uani 1 1 d . . . . .
C1 C 0.1188(8) 0.5428(9) 0.7863(5) 0.0422(12) Uani 0.758(4) 1 d . U P A 1
H1 H 0.0393 0.4496 0.7512 0.051 Uiso 0.758(4) 1 calc R . P A 1
C2 C 0.134(2) 0.6018(16) 0.8852(11) 0.056(3) Uani 0.758(4) 1 d . U P A 1
H2 H 0.0649 0.5573 0.9256 0.067 Uiso 0.758(4) 1 calc R . P A 1
C3 C 0.2710(3) 0.7445(2) 0.92522(17) 0.0317(5) Uani 1 1 d . U . . .
C4 C 0.3474(3) 0.7848(2) 0.84182(17) 0.0303(5) Uani 1 1 d . U . . .
C5 C 0.4771(2) 0.9198(2) 0.85791(17) 0.0295(5) Uani 1 1 d . . . . .
C6 C 0.5367(2) 1.0197(2) 0.95751(16) 0.0282(4) Uani 1 1 d . . . . .
C7 C 0.6686(3) 1.1570(2) 0.97528(17) 0.0312(5) Uani 1 1 d . . . . .
C8 C 0.7435(3) 1.1989(3) 0.88727(18) 0.0368(5) Uani 1 1 d . . . . .
C9 C 0.5510(3) 0.9580(3) 0.76939(17) 0.0332(5) Uani 1 1 d . . . . .
C10 C 0.7519(3) 1.1407(3) 0.70368(18) 0.0351(5) Uani 1 1 d . . . . .
C11 C 0.6843(3) 1.2235(3) 0.63810(19) 0.0413(6) Uani 1 1 d . . . . .
C12 C 0.7553(4) 1.2624(3) 0.5550(2) 0.0542(7) Uani 1 1 d . . . . .
H12 H 0.7126 1.3171 0.5090 0.065 Uiso 1 1 calc R . . . .
C13 C 0.8850(4) 1.2220(4) 0.5402(2) 0.0620(9) Uani 1 1 d . . . . .
H13 H 0.9297 1.2490 0.4842 0.074 Uiso 1 1 calc R . . . .
C14 C 0.9506(4) 1.1418(4) 0.6069(3) 0.0593(9) Uani 1 1 d . . . . .
H14 H 1.0396 1.1153 0.5955 0.071 Uiso 1 1 calc R . . . .
C15 C 0.8867(3) 1.0985(3) 0.6923(2) 0.0453(6) Uani 1 1 d . . . . .
C16 C 0.5444(4) 1.2756(3) 0.6537(2) 0.0514(7) Uani 1 1 d D . . . .
H16 H 0.5090 1.2364 0.7139 0.062 Uiso 0.868(17) 1 calc R . P B 1
H16A H 0.5546 1.3373 0.5985 0.062 Uiso 0.132(17) 1 calc R . P B 2
C17 C 0.4001(5) 1.2202(11) 0.5587(4) 0.076(2) Uani 0.868(17) 1 d . U P B 1
H17A H 0.4306 1.2638 0.5003 0.114 Uiso 0.868(17) 1 calc GR . P B 1
H17B H 0.3132 1.2517 0.5756 0.114 Uiso 0.868(17) 1 calc GR . P B 1
H17C H 0.3649 1.1098 0.5398 0.114 Uiso 0.868(17) 1 calc GR . P B 1
C18 C 0.5984(8) 1.4525(6) 0.6795(9) 0.109(3) Uani 0.868(17) 1 d . U P B 1
H18A H 0.6762 1.4894 0.7471 0.163 Uiso 0.868(17) 1 d R . P B 1
H18B H 0.5051 1.4831 0.6825 0.163 Uiso 0.868(17) 1 d R . P B 1
H18C H 0.6466 1.4953 0.6262 0.163 Uiso 0.868(17) 1 d R . P B 1
C19 C 0.9601(4) 1.0122(4) 0.7659(3) 0.0622(8) Uani 1 1 d . U . . .
H19A H 0.8877 0.9916 0.8134 0.075 Uiso 0.467(17) 1 calc R . P C 2
H19 H 0.9369 1.0293 0.8353 0.075 Uiso 0.533(17) 1 calc R . P C 1
C20 C 0.8867(13) 0.8375(12) 0.7115(12) 0.077(3) Uani 0.533(17) 1 d . U P C 1
H20A H 0.9319 0.7780 0.7558 0.116 Uiso 0.533(17) 1 calc GR . P C 1
H20B H 0.9124 0.8239 0.6441 0.116 Uiso 0.533(17) 1 calc GR . P C 1
H20C H 0.7708 0.8036 0.7011 0.116 Uiso 0.533(17) 1 calc GR . P C 1
C21 C 1.1474(8) 1.0652(10) 0.7758(10) 0.072(3) Uani 0.533(17) 1 d . U P C 1
H21A H 1.2002 1.0330 0.8357 0.108 Uiso 0.533(17) 1 calc GR . P C 1
H21B H 1.1891 1.1755 0.7853 0.108 Uiso 0.533(17) 1 calc GR . P C 1
H21C H 1.1678 1.0195 0.7126 0.108 Uiso 0.533(17) 1 calc GR . P C 1
Cl1B Cl 0.5376(8) 0.5205(11) 0.9543(7) 0.237(4) Uani 0.380(4) 1 d D U P D -1
Cl1D Cl 0.8007(9) 0.7933(8) 0.9506(4) 0.178(3) Uani 0.380(4) 1 d D U P D -1
C17A C 0.400(3) 1.144(4) 0.579(3) 0.069(9) Uani 0.132(17) 1 d D U P B 2
H17D H 0.4174 1.1333 0.5089 0.104 Uiso 0.132(17) 1 calc GR . P B 2
H17E H 0.3019 1.1676 0.5772 0.104 Uiso 0.132(17) 1 calc GR . P B 2
H17F H 0.3917 1.0497 0.6038 0.104 Uiso 0.132(17) 1 calc GR . P B 2
C18A C 0.578(7) 1.418(5) 0.739(4) 0.114(14) Uani 0.132(17) 1 d D U P B 2
H18D H 0.5252 1.3918 0.7944 0.171 Uiso 0.132(17) 1 d R . P B 2
H18E H 0.5408 1.4938 0.7079 0.171 Uiso 0.132(17) 1 d R . P B 2
H18F H 0.6933 1.4594 0.7680 0.171 Uiso 0.132(17) 1 d R . P B 2
C21A C 1.1310(15) 1.1063(15) 0.8430(13) 0.099(4) Uani 0.467(17) 1 d . U P C 2
H21D H 1.1648 1.0423 0.8886 0.148 Uiso 0.467(17) 1 calc GR . P C 2
H21E H 1.1235 1.1950 0.8851 0.148 Uiso 0.467(17) 1 calc GR . P C 2
H21F H 1.2090 1.1390 0.8024 0.148 Uiso 0.467(17) 1 calc GR . P C 2
C20A C 0.959(2) 0.8562(18) 0.7210(14) 0.091(4) Uani 0.467(17) 1 d . U P C 2
H20D H 0.8568 0.8007 0.6714 0.136 Uiso 0.467(17) 1 calc GR . P C 2
H20E H 0.9759 0.8011 0.7771 0.136 Uiso 0.467(17) 1 calc GR . P C 2
H20F H 1.0451 0.8664 0.6854 0.136 Uiso 0.467(17) 1 calc GR . P C 2
S1A S 0.1227(14) 0.5798(12) 0.8954(8) 0.0457(15) Uani 0.242(4) 1 d D U P A 2
C2A C 0.272(3) 0.662(3) 0.7540(16) 0.045(5) Uani 0.242(4) 1 d D U P A 2
H2A H 0.3063 0.6616 0.6918 0.054 Uiso 0.242(4) 1 calc R . P A 2
C1E C 0.143(3) 0.542(3) 0.7653(12) 0.044(4) Uani 0.242(4) 1 d D U P A 2
H1E H 0.0780 0.4571 0.7130 0.053 Uiso 0.242(4) 1 calc R . P A 2
C1A C 0.7460(14) 0.6169(14) 0.9822(15) 0.177(6) Uani 0.380(4) 1 d D U P D -1
H1AA H 0.7919 0.6277 1.0574 0.213 Uiso 0.380(4) 1 calc R . P D -1
H1AB H 0.7941 0.5532 0.9444 0.213 Uiso 0.380(4) 1 calc R . P D -1
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'
S S 0.1246 0.1234 '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
C4 S1 C1 90.0(2) . .
C8 N1 C9 125.10(18) . .
C8 N1 C10 116.88(18) . .
C9 N1 C10 118.01(18) . .
S1 C1 H1 122.2 . .
C2 C1 S1 115.5(8) . .
C2 C1 H1 122.2 . .
C1 C2 H2 123.6 . .
C1 C2 C3 112.8(11) . .
C3 C2 H2 123.6 . .
C4 C3 C2 109.5(6) . .
C4 C3 S1A 115.5(4) . .
C7 C3 C2 131.7(6) 2_677 .
C7 C3 C4 118.85(19) 2_677 .
C7 C3 S1A 125.6(4) 2_677 .
C3 C4 S1 112.21(16) . .
C5 C4 S1 126.71(17) . .
C5 C4 C3 121.1(2) . .
C5 C4 C2A 131.7(9) . .
C2A C4 C3 107.2(8) . .
C4 C5 C6 120.13(19) . .
C4 C5 C9 119.4(2) . .
C6 C5 C9 120.52(19) . .
C5 C6 C6 119.7(2) . 2_677
C7 C6 C5 120.86(19) . .
C7 C6 C6 119.5(2) . 2_677
C3 C7 C6 120.81(19) 2_677 .
C3 C7 C8 119.58(19) 2_677 .
C6 C7 C8 119.6(2) . .
O2 C8 N1 119.5(2) . .
O2 C8 C7 123.2(2) . .
N1 C8 C7 117.34(19) . .
O1 C9 N1 120.72(19) . .
O1 C9 C5 122.7(2) . .
N1 C9 C5 116.56(19) . .
C11 C10 N1 118.2(2) . .
C11 C10 C15 123.7(2) . .
C15 C10 N1 118.1(2) . .
C10 C11 C12 116.8(3) . .
C10 C11 C16 123.6(2) . .
C12 C11 C16 119.6(3) . .
C11 C12 H12 119.3 . .
C13 C12 C11 121.5(3) . .
C13 C12 H12 119.3 . .
C12 C13 H13 119.8 . .
C12 C13 C14 120.5(2) . .
C14 C13 H13 119.8 . .
C13 C14 H14 119.2 . .
C13 C14 C15 121.6(3) . .
C15 C14 H14 119.2 . .
C10 C15 C14 115.9(3) . .
C10 C15 C19 122.7(2) . .
C14 C15 C19 121.4(3) . .
C11 C16 H16 108.3 . .
C11 C16 H16A 92.1 . .
C11 C16 C17 113.8(3) . .
C11 C16 C18 110.3(3) . .
C11 C16 C17A 100.9(13) . .
C11 C16 C18A 119(2) . .
C17 C16 H16 108.3 . .
C17 C16 C18 107.5(7) . .
C18 C16 H16 108.3 . .
C17A C16 H16A 92.1 . .
C18A C16 H16A 92.1 . .
C18A C16 C17A 140(2) . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17B 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C16 C18 H18A 109.0 . .
C16 C18 H18B 108.9 . .
C16 C18 H18C 110.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C15 C19 H19A 103.6 . .
C15 C19 H19 111.2 . .
C15 C19 C20 106.8(6) . .
C15 C19 C21 108.3(4) . .
C15 C19 C21A 116.1(5) . .
C20 C19 H19 111.2 . .
C21 C19 H19 111.2 . .
C21 C19 C20 107.9(5) . .
C21A C19 H19A 103.6 . .
C20A C19 C15 118.1(7) . .
C20A C19 H19A 103.6 . .
C20A C19 C21A 109.6(7) . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C19 C21 H21A 109.5 . .
C19 C21 H21B 109.5 . .
C19 C21 H21C 109.5 . .
H21A C21 H21B 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C16 C17A H17D 109.5 . .
C16 C17A H17E 109.5 . .
C16 C17A H17F 109.5 . .
H17D C17A H17E 109.5 . .
H17D C17A H17F 109.5 . .
H17E C17A H17F 109.5 . .
C16 C18A H18D 111.4 . .
C16 C18A H18E 110.0 . .
C16 C18A H18F 107.0 . .
H18D C18A H18E 109.5 . .
H18D C18A H18F 109.5 . .
H18E C18A H18F 109.5 . .
C19 C21A H21D 109.5 . .
C19 C21A H21E 109.5 . .
C19 C21A H21F 109.5 . .
H21D C21A H21E 109.5 . .
H21D C21A H21F 109.5 . .
H21E C21A H21F 109.5 . .
C19 C20A H20D 109.5 . .
C19 C20A H20E 109.5 . .
C19 C20A H20F 109.5 . .
H20D C20A H20E 109.5 . .
H20D C20A H20F 109.5 . .
H20E C20A H20F 109.5 . .
C3 S1A C1E 92.6(10) . .
C4 C2A H2A 121.8 . .
C1E C2A C4 116.4(17) . .
C1E C2A H2A 121.8 . .
S1A C1E H1E 125.9 . .
C2A C1E S1A 108.2(15) . .
C2A C1E H1E 125.9 . .
Cl1B C1A H1AA 108.4 . .
Cl1B C1A H1AB 108.4 . .
Cl1D C1A Cl1B 115.6(8) . .
Cl1D C1A H1AA 108.4 . .
Cl1D C1A H1AB 108.4 . .
H1AA C1A H1AB 107.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.731(5) .
S1 C4 1.729(3) .
O1 C9 1.207(3) .
O2 C8 1.212(3) .
N1 C8 1.390(3) .
N1 C9 1.397(3) .
N1 C10 1.458(2) .
C1 H1 0.9300 .
C1 C2 1.310(13) .
C2 H2 0.9300 .
C2 C3 1.457(14) .
C3 C4 1.433(3) .
C3 C7 1.400(3) 2_677
C3 S1A 1.634(10) .
C4 C5 1.385(3) .
C4 C2A 1.41(2) .
C5 C6 1.407(3) .
C5 C9 1.477(3) .
C6 C6 1.435(4) 2_677
C6 C7 1.407(3) .
C7 C3 1.400(3) 2_677
C7 C8 1.483(3) .
C10 C11 1.387(4) .
C10 C15 1.397(3) .
C11 C12 1.400(3) .
C11 C16 1.504(4) .
C12 H12 0.9300 .
C12 C13 1.356(5) .
C13 H13 0.9300 .
C13 C14 1.370(5) .
C14 H14 0.9300 .
C14 C15 1.405(4) .
C15 C19 1.500(4) .
C16 H16 0.9800 .
C16 H16A 0.9800 .
C16 C17 1.509(5) .
C16 C18 1.536(6) .
C16 C17A 1.537(10) .
C16 C18A 1.535(10) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9599 .
C18 H18C 0.9600 .
C19 H19A 0.9800 .
C19 H19 0.9800 .
C19 C20 1.567(12) .
C19 C21 1.564(7) .
C19 C21A 1.572(11) .
C19 C20A 1.489(16) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
Cl1B C1A 1.741(9) .
Cl1D C1A 1.691(9) .
C17A H17D 0.9600 .
C17A H17E 0.9600 .
C17A H17F 0.9600 .
C18A H18D 0.9599 .
C18A H18E 0.9600 .
C18A H18F 0.9600 .
C21A H21D 0.9600 .
C21A H21E 0.9600 .
C21A H21F 0.9600 .
C20A H20D 0.9600 .
C20A H20E 0.9600 .
C20A H20F 0.9600 .
S1A C1E 1.757(10) .
C2A H2A 0.9300 .
C2A C1E 1.386(10) .
C1E H1E 0.9300 .
C1A H1AA 0.9700 .
C1A H1AB 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_4
S1 C1 C2 C3 -2.6(16) . .
S1 C4 C5 C6 179.2(2) . .
S1 C4 C5 C9 -0.4(3) . .
S1 C4 C2A C1E -139(13) . .
N1 C10 C11 C12 -179.3(2) . .
N1 C10 C11 C16 2.3(4) . .
N1 C10 C15 C14 179.3(2) . .
N1 C10 C15 C19 -0.7(4) . .
C1 S1 C4 C3 0.4(4) . .
C1 S1 C4 C5 -178.5(4) . .
C1 S1 C4 C2A 39(11) . .
C1 C2 C3 C4 2.7(14) . .
C1 C2 C3 C7 -179.2(7) . 2_677
C1 C2 C3 S1A -145(10) . .
C2 C3 C4 S1 -1.8(8) . .
C2 C3 C4 C5 177.2(7) . .
C2 C3 C4 C2A -6.0(15) . .
C2 C3 S1A C1E 34(8) . .
C3 C4 C5 C6 0.4(3) . .
C3 C4 C5 C9 -179.2(2) . .
C3 C4 C2A C1E 3(3) . .
C3 C7 C8 O2 -0.1(4) 2_677 .
C3 C7 C8 N1 179.6(2) 2_677 .
C3 S1A C1E C2A 2(2) . .
C4 S1 C1 C2 1.3(11) . .
C4 C3 S1A C1E -0.2(12) . .
C4 C5 C6 C6 0.5(4) . 2_677
C4 C5 C6 C7 179.8(2) . .
C4 C5 C9 O1 -1.0(4) . .
C4 C5 C9 N1 179.0(2) . .
C4 C2A C1E S1A -4(3) . .
C5 C4 C2A C1E 179.7(17) . .
C5 C6 C7 C3 -179.3(2) . 2_677
C5 C6 C7 C8 1.4(3) . .
C6 C5 C9 O1 179.5(2) . .
C6 C5 C9 N1 -0.5(3) . .
C6 C6 C7 C3 0.1(4) 2_677 2_677
C6 C6 C7 C8 -179.3(2) 2_677 .
C6 C7 C8 O2 179.2(2) . .
C6 C7 C8 N1 -1.0(3) . .
C7 C3 C4 S1 179.93(19) 2_677 .
C7 C3 C4 C5 -1.1(3) 2_677 .
C7 C3 C4 C2A 175.7(13) 2_677 .
C7 C3 S1A C1E -177.4(11) 2_677 .
C8 N1 C9 O1 -179.1(2) . .
C8 N1 C9 C5 0.9(3) . .
C8 N1 C10 C11 -91.2(3) . .
C8 N1 C10 C15 88.1(3) . .
C9 N1 C8 O2 179.6(2) . .
C9 N1 C8 C7 -0.1(4) . .
C9 N1 C10 C11 87.8(3) . .
C9 N1 C10 C15 -93.0(3) . .
C9 C5 C6 C6 -180.0(2) . 2_677
C9 C5 C6 C7 -0.6(3) . .
C10 N1 C8 O2 -1.5(4) . .
C10 N1 C8 C7 178.7(2) . .
C10 N1 C9 O1 2.1(4) . .
C10 N1 C9 C5 -178.0(2) . .
C10 C11 C12 C13 -0.6(4) . .
C10 C11 C16 C17 -123.5(5) . .
C10 C11 C16 C18 115.5(6) . .
C10 C11 C16 C17A -95.3(19) . .
C10 C11 C16 C18A 79(3) . .
C10 C15 C19 C20 96.7(5) . .
C10 C15 C19 C21 -147.4(6) . .
C10 C15 C19 C21A -109.1(9) . .
C10 C15 C19 C20A 117.7(9) . .
C11 C10 C15 C14 -1.6(4) . .
C11 C10 C15 C19 178.5(3) . .
C11 C12 C13 C14 -0.2(5) . .
C12 C11 C16 C17 58.2(5) . .
C12 C11 C16 C18 -62.8(6) . .
C12 C11 C16 C17A 86.4(19) . .
C12 C11 C16 C18A -100(3) . .
C12 C13 C14 C15 0.1(5) . .
C13 C14 C15 C10 0.7(4) . .
C13 C14 C15 C19 -179.3(3) . .
C14 C15 C19 C20 -83.3(5) . .
C14 C15 C19 C21 32.6(6) . .
C14 C15 C19 C21A 71.0(9) . .
C14 C15 C19 C20A -62.3(9) . .
C15 C10 C11 C12 1.5(4) . .
C15 C10 C11 C16 -176.9(2) . .
C16 C11 C12 C13 177.9(3) . .
S1A C3 C4 S1 2.6(6) . .
S1A C3 C4 C5 -178.5(5) . .
S1A C3 C4 C2A -1.7(14) . .
C2A C4 C5 C6 -175.5(16) . .
C2A C4 C5 C9 4.9(17) . .
