#------------------------------------------------------------------------------
#$Date: 2015-09-24 14:30:16 +0300 (Thu, 24 Sep 2015) $
#$Revision: 158281 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/78/7117836.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_7117836
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, 2(C H2 Cl2)'
_chemical_formula_sum            'C74 H58 Cl4 N2 O8'
_chemical_formula_weight         1245.02
_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             2015-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-07-12 deposited with the CCDC.
2015-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.491(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.1824(9)
_cell_length_b                   10.3899(5)
_cell_length_c                   17.8902(9)
_cell_measurement_reflns_used    9762
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.32
_cell_volume                     2929.1(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEXII v2014.9-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            142111
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        27.900
_diffrn_reflns_theta_max         27.919
_diffrn_reflns_theta_min         2.320
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0707 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.9637.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       plate
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         7012
_refine_ls_number_restraints     50
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0371
_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)+(0.0447P)²+1.7845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                6168
_reflns_number_total             7012
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc06140g2.cif.txt
_cod_data_source_block           dfya53_dcm_0m
_cod_database_code               7117836
_shelxl_version_number           2014/6
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C16A, C16B}
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1S_1) = Uanis(Cl1S_2)
Uanis(C1S_1) = Uanis(C1S_2)
Uanis(Cl2S_1) = Uanis(Cl2S_2)
Uanis(C16A) = Uanis(C16B)
Uanis(C17A) = Uanis(C17B)
Uanis(C18A) = Uanis(C18B)
Uanis(C19A) = Uanis(C19B)
Uanis(C20A) = Uanis(C20B)
Uanis(C21A) = Uanis(C21B)
Uanis(C22A) = Uanis(C22B)
Uanis(C23A) = Uanis(C23B)
Uanis(C24A) = Uanis(C24B)
Uanis(C25A) = Uanis(C25B)
Uanis(C26A) = Uanis(C26B)
Uanis(C27A) = Uanis(C27B)
Uanis(C28A) = Uanis(C28B)
Uanis(C29A) = Uanis(C29B)
Uanis(C30A) = Uanis(C30B)
Uanis(C31A) = Uanis(C31B)
4. Same fragment restrains
{C16A, C17A, C18A, C19A, C20A, C21A, C22A, C23A, C24A, C25A, C26A, C27A, C28A,
C29A, C30A, C31A} sigma for 1-2: 0.01, 1-3: 0.04
as
{C16B, C17B, C18B, C19B, C20B, C21B, C22B, C23B, C24B, C25B, C26B, C27B, C28B,
C29B, C30B, C31B}
{C1S_1, Cl2S_1, Cl1S_1} sigma for 1-2: 0.01, 1-3: 0.04
as
{C1S_2, Cl2S_2, Cl1S_2}
5. Others
 Sof(H15C)=Sof(H15D)=Sof(C16B)=Sof(C17B)=Sof(C18B)=Sof(H18B)=Sof(C19B)=
 Sof(H19B)=Sof(C20B)=Sof(C21B)=Sof(C22B)=Sof(C23B)=Sof(C24B)=Sof(H24B)=
 Sof(C25B)=Sof(H25B)=Sof(C26B)=Sof(H26B)=Sof(C27B)=Sof(H27B)=Sof(C28B)=
 Sof(H28B)=Sof(C29B)=Sof(C30B)=Sof(H30B)=Sof(C31B)=Sof(H31B)=1-FVAR(1)
 Sof(H15A)=Sof(H15B)=Sof(C16A)=Sof(C17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=
 Sof(H19A)=Sof(C20A)=Sof(C21A)=Sof(C22A)=Sof(C23A)=Sof(C24A)=Sof(H24A)=
 Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(H26A)=Sof(C27A)=Sof(H27A)=Sof(C28A)=
 Sof(H28A)=Sof(C29A)=Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(H31A)=FVAR(1)
 Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(Cl2S)=Sof(Cl1S)=1-FVAR(2)
 Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(Cl2S)=Sof(Cl1S)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C15(H15C,H15D), C35(H35A,H35B), C1S(H1SA,H1SB), C1S(H1SA,H1SB)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C18A(H18A), C19A(H19A),
 C24A(H24A), C25A(H25A), C26A(H26A), C27A(H27A), C28A(H28A), C30A(H30A),
 C31A(H31A), C18B(H18B), C19B(H19B), C24B(H24B), C25B(H25B), C26B(H26B),
 C27B(H27B), C28B(H28B), C30B(H30B), C31B(H31B)
6.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C36(H36A,H36B,H36C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.23846(5) 0.42254(10) 0.40083(5) 0.01848(19) Uani 1 1 d . . . . .
O2 O 0.39149(6) 0.47726(10) 0.67250(5) 0.0200(2) Uani 1 1 d . . . . .
O3 O 0.19983(5) 0.63327(8) 0.51330(5) 0.01556(18) Uani 1 1 d . . . . .
O4 O 0.09042(6) 0.61474(10) 0.38992(6) 0.0227(2) Uani 1 1 d . . . . .
N1 N 0.31690(6) 0.44037(10) 0.53703(6) 0.0119(2) Uani 1 1 d . . . . .
C1 C 0.30744(7) 0.44137(11) 0.45548(7) 0.0115(2) Uani 1 1 d . . . . .
C2 C 0.38535(7) 0.46456(11) 0.44106(7) 0.0102(2) Uani 1 1 d . . . . .
C3 C 0.46298(7) 0.48996(10) 0.50745(7) 0.0092(2) Uani 1 1 d . . . . .
C4 C 0.46825(7) 0.49635(11) 0.58822(7) 0.0107(2) Uani 1 1 d . . . . .
C5 C 0.39169(7) 0.47213(11) 0.60502(7) 0.0123(2) Uani 1 1 d . . . . .
C6 C 0.38165(7) 0.45925(11) 0.36264(7) 0.0124(2) Uani 1 1 d . . . . .
H6 H 0.3291 0.4427 0.3184 0.015 Uiso 1 1 calc R U . . .
C7 C 0.54469(7) 0.52172(12) 0.65203(7) 0.0128(2) Uani 1 1 d . . . . .
H7 H 0.5476 0.5264 0.7061 0.015 Uiso 1 1 calc R U . . .
C8 C 0.24192(7) 0.41671(12) 0.55277(7) 0.0123(2) Uani 1 1 d . . . . .
C9 C 0.18252(7) 0.51352(12) 0.53871(7) 0.0129(2) Uani 1 1 d . . . . .
C10 C 0.11189(7) 0.49448(12) 0.55595(7) 0.0154(2) Uani 1 1 d . . . . .
H10 H 0.0716 0.5616 0.5469 0.018 Uiso 1 1 calc R U . . .
C11 C 0.10006(7) 0.37623(12) 0.58662(8) 0.0156(2) Uani 1 1 d . . . . .
H11 H 0.0515 0.3638 0.5987 0.019 Uiso 1 1 calc R U . . .
C12 C 0.15793(7) 0.27563(12) 0.60007(7) 0.0144(2) Uani 1 1 d . . . . .
C13 C 0.22978(7) 0.29936(12) 0.58302(7) 0.0147(2) Uani 1 1 d . . . . .
H13 H 0.2709 0.2333 0.5925 0.018 Uiso 1 1 calc R U . . .
C14 C 0.14919(7) 0.67460(13) 0.43674(8) 0.0162(2) Uani 1 1 d . . . . .
C15 C 0.17865(8) 0.80566(13) 0.42234(9) 0.0196(3) Uani 1 1 d . . . . .
H15A H 0.1848 0.8624 0.4688 0.024 Uiso 0.760(3) 1 calc R U P A 1
H15B H 0.1347 0.8436 0.3727 0.024 Uiso 0.760(3) 1 calc R U P A 1
H15C H 0.1848 0.8624 0.4688 0.024 Uiso 0.240(3) 1 calc R U P A 2
H15D H 0.1347 0.8436 0.3727 0.024 Uiso 0.240(3) 1 calc R U P A 2
C16A C 0.26244(8) 0.80173(12) 0.41238(8) 0.0167(2) Uani 0.760(3) 1 d D . P A 1
C17A C 0.3426(2) 0.815(2) 0.4768(2) 0.0156(4) Uani 0.760(3) 1 d D . P A 1
C18A C 0.35526(17) 0.8262(7) 0.5607(2) 0.0191(6) Uani 0.760(3) 1 d D . P A 1
H18A H 0.3076 0.8226 0.5749 0.023 Uiso 0.760(3) 1 calc R U P A 1
C19A C 0.43388(15) 0.8422(3) 0.62037(16) 0.0226(5) Uani 0.760(3) 1 d D . P A 1
H19A H 0.4400 0.8491 0.6754 0.027 Uiso 0.760(3) 1 calc R U P A 1
C20A C 0.50773(13) 0.8488(2) 0.60221(14) 0.0208(5) Uani 0.760(3) 1 d D . P A 1
C21A C 0.49772(13) 0.8358(2) 0.52011(14) 0.0183(5) Uani 0.760(3) 1 d D . P A 1
C22A C 0.41525(17) 0.8173(4) 0.45681(13) 0.0162(5) Uani 0.760(3) 1 d D . P A 1
C23A C 0.40635(14) 0.8054(3) 0.37497(14) 0.0172(5) Uani 0.760(3) 1 d D . P A 1
C24A C 0.32551(14) 0.7908(3) 0.31320(14) 0.0187(5) Uani 0.760(3) 1 d D . P A 1
H24A H 0.3190 0.7812 0.2582 0.022 Uiso 0.760(3) 1 calc R U P A 1
C25A C 0.25444(14) 0.7904(5) 0.33215(15) 0.0183(5) Uani 0.760(3) 1 d D . P A 1
H25A H 0.1996 0.7824 0.2896 0.022 Uiso 0.760(3) 1 calc R U P A 1
C26A C 0.58907(13) 0.8709(2) 0.66290(15) 0.0290(5) Uani 0.760(3) 1 d D . P A 1
H26A H 0.5964 0.8806 0.7181 0.035 Uiso 0.760(3) 1 calc R U P A 1
C27A C 0.65880(13) 0.8786(2) 0.64214(19) 0.0326(7) Uani 0.760(3) 1 d D . P A 1
H27A H 0.7136 0.8927 0.6837 0.039 Uiso 0.760(3) 1 calc R U P A 1
C28A C 0.64998(12) 0.86605(19) 0.56257(19) 0.0306(6) Uani 0.760(3) 1 d D . P A
1
H28A H 0.6986 0.8718 0.5500 0.037 Uiso 0.760(3) 1 calc R U P A 1
C29A C 0.57004(12) 0.84488(19) 0.49976(18) 0.0224(5) Uani 0.760(3) 1 d D . P A
1
C30A C 0.55800(14) 0.83394(19) 0.41651(19) 0.0259(5) Uani 0.760(3) 1 d D . P A
1
H30A H 0.6057 0.8412 0.4026 0.031 Uiso 0.760(3) 1 calc R U P A 1
C31A C 0.48107(15) 0.8137(2) 0.35733(16) 0.0248(5) Uani 0.760(3) 1 d D . P A 1
H31A H 0.4757 0.8047 0.3026 0.030 Uiso 0.760(3) 1 calc R U P A 1
C16B C 0.26244(8) 0.80173(12) 0.41238(8) 0.0167(2) Uani 0.240(3) 1 d D . P A 2
C17B C 0.3393(6) 0.814(7) 0.4833(7) 0.0156(4) Uani 0.240(3) 1 d D . P A 2
C18B C 0.3406(7) 0.831(2) 0.5638(7) 0.0191(6) Uani 0.240(3) 1 d D . P A 2
H18B H 0.2888 0.8271 0.5708 0.023 Uiso 0.240(3) 1 calc R U P A 2
C19B C 0.4140(5) 0.8542(11) 0.6299(6) 0.0226(5) Uani 0.240(3) 1 d D . P A 2
H19B H 0.4114 0.8660 0.6815 0.027 Uiso 0.240(3) 1 calc R U P A 2
C20B C 0.4937(4) 0.8606(8) 0.6246(5) 0.0208(5) Uani 0.240(3) 1 d D . P A 2
C21B C 0.4973(5) 0.8441(9) 0.5480(5) 0.0183(5) Uani 0.240(3) 1 d D . P A 2
C22B C 0.4206(6) 0.8182(17) 0.4776(5) 0.0162(5) Uani 0.240(3) 1 d D . P A 2
C23B C 0.4246(5) 0.8051(11) 0.4009(5) 0.0172(5) Uani 0.240(3) 1 d D . P A 2
C24B C 0.3514(5) 0.7863(10) 0.3338(5) 0.0187(5) Uani 0.240(3) 1 d D . P A 2
H24B H 0.3539 0.7750 0.2821 0.022 Uiso 0.240(3) 1 calc R U P A 2
C25B C 0.2733(6) 0.7835(19) 0.3395(5) 0.0183(5) Uani 0.240(3) 1 d D . P A 2
H25B H 0.2242 0.7682 0.2912 0.022 Uiso 0.240(3) 1 calc R U P A 2
C26B C 0.5712(4) 0.8861(7) 0.6918(5) 0.0290(5) Uani 0.240(3) 1 d D . P A 2
H26B H 0.5718 0.8960 0.7449 0.035 Uiso 0.240(3) 1 calc R U P A 2
C27B C 0.6463(4) 0.8966(7) 0.6800(5) 0.0326(7) Uani 0.240(3) 1 d D . P A 2
H27B H 0.6974 0.9152 0.7257 0.039 Uiso 0.240(3) 1 calc R U P A 2
C28B C 0.6495(5) 0.8814(9) 0.6053(6) 0.0306(6) Uani 0.240(3) 1 d D . P A 2
H28B H 0.7020 0.8890 0.5997 0.037 Uiso 0.240(3) 1 calc R U P A 2
C29B C 0.5750(4) 0.8545(7) 0.5371(5) 0.0224(5) Uani 0.240(3) 1 d D . P A 2
C30B C 0.5746(5) 0.8400(7) 0.4584(6) 0.0259(5) Uani 0.240(3) 1 d D . P A 2
H30B H 0.6268 0.8489 0.4523 0.031 Uiso 0.240(3) 1 calc R U P A 2
C31B C 0.5051(5) 0.8148(8) 0.3928(5) 0.0248(5) Uani 0.240(3) 1 d D . P A 2
H31B H 0.5079 0.8033 0.3413 0.030 Uiso 0.240(3) 1 calc R U P A 2
C32 C 0.14735(8) 0.14429(12) 0.63419(8) 0.0178(3) Uani 1 1 d . . . . .
C33 C 0.06239(9) 0.13284(14) 0.64300(9) 0.0248(3) Uani 1 1 d . . . . .
H33A H 0.0585 0.2005 0.6795 0.037 Uiso 1 1 calc R U . . .
H33B H 0.0587 0.0483 0.6657 0.037 Uiso 1 1 calc R U . . .
H33C H 0.0157 0.1424 0.5894 0.037 Uiso 1 1 calc R U . . .
C34 C 0.15091(10) 0.03675(14) 0.57666(10) 0.0282(3) Uani 1 1 d . . . . .
H34A H 0.1051 0.0490 0.5228 0.042 Uiso 1 1 calc R U . . .
H34B H 0.1442 -0.0469 0.5987 0.042 Uiso 1 1 calc R U . . .
H34C H 0.2057 0.0396 0.5718 0.042 Uiso 1 1 calc R U . . .
C35 C 0.22132(9) 0.12303(14) 0.71826(9) 0.0237(3) Uani 1 1 d . . . . .
H35A H 0.2134 0.0386 0.7399 0.028 Uiso 1 1 calc R U . . .
H35B H 0.2751 0.1191 0.7103 0.028 Uiso 1 1 calc R U . . .
C36 C 0.22964(11) 0.22512(17) 0.78101(9) 0.0337(4) Uani 1 1 d . . . . .
H36A H 0.2363 0.3096 0.7599 0.050 Uiso 1 1 calc R U . . .
H36B H 0.2794 0.2068 0.8311 0.050 Uiso 1 1 calc R U . . .
H36C H 0.1786 0.2253 0.7928 0.050 Uiso 1 1 calc R U . . .
C1S_1 C 0.43202(11) 0.7836(2) 0.12585(13) 0.0261(5) Uani 0.861(3) 1 d D . P B 1
H1SA_1 H 0.4161 0.7967 0.0668 0.031 Uiso 0.861(3) 1 calc R U P B 1
H1SB_1 H 0.4109 0.8581 0.1468 0.031 Uiso 0.861(3) 1 calc R U P B 1
Cl2S_1 Cl 0.54342(3) 0.77581(13) 0.17595(5) 0.0386(2) Uani 0.861(3) 1 d D . P B
1
Cl1S_1 Cl 0.38365(6) 0.64047(10) 0.14112(7) 0.02654(16) Uani 0.861(3) 1 d D . P
B 1
C1S_2 C 0.4319(6) 0.8170(11) 0.1418(11) 0.0261(5) Uani 0.139(3) 1 d D . P B 2
H1SA_2 H 0.4145 0.8430 0.0842 0.031 Uiso 0.139(3) 1 calc R U P B 2
H1SB_2 H 0.4043 0.8758 0.1675 0.031 Uiso 0.139(3) 1 calc R U P B 2
Cl2S_2 Cl 0.5429(2) 0.8280(7) 0.1930(3) 0.0386(2) Uani 0.139(3) 1 d D . P B 2
Cl1S_2 Cl 0.3990(5) 0.6566(8) 0.1466(5) 0.02654(16) Uani 0.139(3) 1 d D . P B 2
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 118.23(10) . .
C1 N1 C5 125.65(9) . .
C1 N1 C8 117.48(9) . .
C5 N1 C8 116.60(9) . .
O1 C1 N1 120.50(10) . .
O1 C1 C2 123.10(11) . .
N1 C1 C2 116.40(10) . .
C3 C2 C1 120.01(10) . .
C6 C2 C1 119.48(10) . .
C6 C2 C3 120.51(10) . .
C2 C3 C3 119.17(13) . 3_666
C4 C3 C2 121.51(10) . .
C4 C3 C3 119.32(13) . 3_666
C3 C4 C5 119.92(10) . .
C7 C4 C3 120.47(10) . .
C7 C4 C5 119.58(10) . .
O2 C5 N1 120.42(10) . .
O2 C5 C4 123.39(11) . .
N1 C5 C4 116.19(10) . .
C2 C6 H6 119.9 . .
C2 C6 C7 120.29(10) . 3_666
C7 C6 H6 119.9 3_666 .
C4 C7 C6 120.24(10) . 3_666
C4 C7 H7 119.9 . .
C6 C7 H7 119.9 3_666 .
C9 C8 N1 119.44(11) . .
C9 C8 C13 119.80(10) . .
C13 C8 N1 120.75(10) . .
C8 C9 O3 118.02(10) . .
C10 C9 O3 121.37(11) . .
C10 C9 C8 120.40(11) . .
C9 C10 H10 120.2 . .
C9 C10 C11 119.59(11) . .
C11 C10 H10 120.2 . .
C10 C11 H11 119.3 . .
C10 C11 C12 121.50(11) . .
C12 C11 H11 119.3 . .
C11 C12 C13 117.26(11) . .
C11 C12 C32 123.03(11) . .
C13 C12 C32 119.70(11) . .
C8 C13 C12 121.44(11) . .
C8 C13 H13 119.3 . .
C12 C13 H13 119.3 . .
O3 C14 C15 109.36(11) . .
O4 C14 O3 124.08(12) . .
O4 C14 C15 126.55(12) . .
C14 C15 H15A 108.9 . .
C14 C15 H15B 108.9 . .
C14 C15 H15C 108.9 . .
C14 C15 H15D 108.9 . .
C14 C15 C16A 113.16(10) . .
C14 C15 C16B 113.16(10) . .
H15A C15 H15B 107.8 . .
H15C C15 H15D 107.8 . .
C16A C15 H15A 108.9 . .
C16A C15 H15B 108.9 . .
C16B C15 H15C 108.9 . .
C16B C15 H15D 108.9 . .
C17A C16A C15 124.45(18) . .
C25A C16A C15 114.49(14) . .
C25A C16A C17A 121.00(19) . .
C16A C17A C18A 123.8(3) . .
C16A C17A C22A 117.7(2) . .
C22A C17A C18A 118.5(2) . .
C17A C18A H18A 119.3 . .
C19A C18A C17A 121.5(2) . .
C19A C18A H18A 119.3 . .
C18A C19A H19A 119.3 . .
C18A C19A C20A 121.5(2) . .
C20A C19A H19A 119.3 . .
C21A C20A C19A 118.60(18) . .
C26A C20A C19A 122.1(2) . .
C26A C20A C21A 119.3(2) . .
C20A C21A C22A 120.43(18) . .
C20A C21A C29A 119.94(19) . .
C29A C21A C22A 119.6(2) . .
C17A C22A C21A 119.55(19) . .
C23A C22A C17A 120.8(2) . .
C23A C22A C21A 119.7(2) . .
C22A C23A C31A 118.85(19) . .
C24A C23A C22A 119.4(2) . .
C24A C23A C31A 121.7(2) . .
C23A C24A H24A 120.0 . .
C25A C24A C23A 120.0(2) . .
C25A C24A H24A 120.0 . .
C16A C25A C24A 121.0(2) . .
C16A C25A H25A 119.5 . .
C24A C25A H25A 119.5 . .
C20A C26A H26A 120.0 . .
C27A C26A C20A 120.0(2) . .
C27A C26A H26A 120.0 . .
C26A C27A H27A 119.4 . .
C28A C27A C26A 121.29(19) . .
C28A C27A H27A 119.4 . .
C27A C28A H28A 119.6 . .
C27A C28A C29A 120.8(2) . .
C29A C28A H28A 119.6 . .
C28A C29A C21A 118.6(2) . .
C28A C29A C30A 122.6(2) . .
C30A C29A C21A 118.81(17) . .
C29A C30A H30A 119.2 . .
C31A C30A C29A 121.67(18) . .
C31A C30A H30A 119.2 . .
C23A C31A H31A 119.3 . .
C30A C31A C23A 121.4(2) . .
C30A C31A H31A 119.3 . .
C17B C16B C15 118.5(5) . .
C25B C16B C15 126.6(4) . .
C25B C16B C17B 114.8(7) . .
C16B C17B C18B 122.7(9) . .
C16B C17B C22B 121.3(8) . .
C22B C17B C18B 115.9(8) . .
C17B C18B H18B 119.0 . .
C19B C18B C17B 122.0(10) . .
C19B C18B H18B 119.0 . .
C18B C19B H19B 118.8 . .
C18B C19B C20B 122.4(9) . .
C20B C19B H19B 118.8 . .
C19B C20B C26B 124.0(7) . .
C21B C20B C19B 118.8(7) . .
C21B C20B C26B 117.2(7) . .
C20B C21B C22B 119.6(7) . .
C20B C21B C29B 122.0(7) . .
C29B C21B C22B 118.4(7) . .
C21B C22B C17B 121.3(8) . .
C23B C22B C17B 119.5(8) . .
C23B C22B C21B 119.1(8) . .
C22B C23B C31B 120.7(7) . .
C24B C23B C22B 119.0(7) . .
C24B C23B C31B 120.3(7) . .
C23B C24B H24B 119.4 . .
C23B C24B C25B 121.3(9) . .
C25B C24B H24B 119.4 . .
C16B C25B H25B 118.1 . .
C24B C25B C16B 123.9(9) . .
C24B C25B H25B 118.1 . .
C20B C26B H26B 120.0 . .
C27B C26B C20B 119.9(7) . .
C27B C26B H26B 120.0 . .
C26B C27B H27B 118.7 . .
C28B C27B C26B 122.6(7) . .
C28B C27B H27B 118.7 . .
C27B C28B H28B 120.2 . .
C27B C28B C29B 119.7(8) . .
C29B C28B H28B 120.2 . .
C28B C29B C21B 118.5(7) . .
C28B C29B C30B 121.9(7) . .
C30B C29B C21B 119.6(6) . .
C29B C30B H30B 118.4 . .
C31B C30B C29B 123.3(7) . .
C31B C30B H30B 118.4 . .
C23B C31B H31B 120.5 . .
C30B C31B C23B 118.9(7) . .
C30B C31B H31B 120.5 . .
C12 C32 C34 109.72(10) . .
C12 C32 C35 109.34(10) . .
C33 C32 C12 112.22(11) . .
C33 C32 C34 107.82(11) . .
C33 C32 C35 109.57(11) . .
C34 C32 C35 108.07(11) . .
C32 C33 H33A 109.5 . .
C32 C33 H33B 109.5 . .
C32 C33 H33C 109.5 . .
H33A C33 H33B 109.5 . .
H33A C33 H33C 109.5 . .
H33B C33 H33C 109.5 . .
C32 C34 H34A 109.5 . .
C32 C34 H34B 109.5 . .
C32 C34 H34C 109.5 . .
H34A C34 H34B 109.5 . .
H34A C34 H34C 109.5 . .
H34B C34 H34C 109.5 . .
C32 C35 H35A 108.6 . .
C32 C35 H35B 108.6 . .
H35A C35 H35B 107.5 . .
C36 C35 C32 114.81(12) . .
C36 C35 H35A 108.6 . .
C36 C35 H35B 108.6 . .
C35 C36 H36A 109.5 . .
C35 C36 H36B 109.5 . .
C35 C36 H36C 109.5 . .
H36A C36 H36B 109.5 . .
H36A C36 H36C 109.5 . .
H36B C36 H36C 109.5 . .
H1SA_1 C1S_1 H1SB_1 108.0 . .
Cl2S_1 C1S_1 H1SA_1 109.4 . .
Cl2S_1 C1S_1 H1SB_1 109.4 . .
Cl2S_1 C1S_1 Cl1S_1 111.29(11) . .
Cl1S_1 C1S_1 H1SA_1 109.4 . .
Cl1S_1 C1S_1 H1SB_1 109.4 . .
H1SA_2 C1S_2 H1SB_2 108.2 . .
Cl2S_2 C1S_2 H1SA_2 109.7 . .
Cl2S_2 C1S_2 H1SB_2 109.7 . .
Cl2S_2 C1S_2 Cl1S_2 109.6(6) . .
Cl1S_2 C1S_2 H1SA_2 109.7 . .
Cl1S_2 C1S_2 H1SB_2 109.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2145(15) .
O2 C5 1.2098(15) .
O3 C9 1.3968(14) .
O3 C14 1.3666(15) .
O4 C14 1.1974(16) .
N1 C1 1.4022(15) .
N1 C5 1.4120(15) .
N1 C8 1.4453(14) .
C1 C2 1.4805(15) .
C2 C3 1.4129(15) .
C2 C6 1.3800(16) .
C3 C3 1.415(2) 3_666
C3 C4 1.4129(15) .
C4 C5 1.4831(15) .
C4 C7 1.3793(16) .
C6 H6 0.9500 .
C6 C7 1.4052(16) 3_666
C7 C6 1.4052(16) 3_666
C7 H7 0.9500 .
C8 C9 1.3827(17) .
C8 C13 1.3831(17) .
C9 C10 1.3803(16) .
C10 H10 0.9500 .
C10 C11 1.3931(18) .
C11 H11 0.9500 .
C11 C12 1.3959(17) .
C12 C13 1.4065(16) .
C12 C32 1.5350(17) .
C13 H13 0.9500 .
C14 C15 1.5102(18) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C15 H15C 0.9900 .
C15 H15D 0.9900 .
C15 C16A 1.5201(17) .
C15 C16B 1.5201(17) .
C16A C17A 1.406(3) .
C16A C25A 1.391(3) .
C17A C18A 1.434(3) .
C17A C22A 1.429(3) .
C18A H18A 0.9500 .
C18A C19A 1.357(3) .
C19A H19A 0.9500 .
C19A C20A 1.431(3) .
C20A C21A 1.416(3) .
C20A C26A 1.405(3) .
C21A C22A 1.431(3) .
C21A C29A 1.431(3) .
C22A C23A 1.416(3) .
C23A C24A 1.396(3) .
C23A C31A 1.442(3) .
C24A H24A 0.9500 .
C24A C25A 1.392(3) .
C25A H25A 0.9500 .
C26A H26A 0.9500 .
C26A C27A 1.391(4) .
C27A H27A 0.9500 .
C27A C28A 1.376(4) .
C28A H28A 0.9500 .
C28A C29A 1.402(3) .
C29A C30A 1.424(3) .
C30A H30A 0.9500 .
C30A C31A 1.340(3) .
C31A H31A 0.9500 .
C16B C17B 1.427(7) .
C16B C25B 1.401(8) .
C17B C18B 1.441(8) .
C17B C22B 1.441(8) .
C18B H18B 0.9500 .
C18B C19B 1.362(8) .
C19B H19B 0.9500 .
C19B C20B 1.412(7) .
C20B C21B 1.406(7) .
C20B C26B 1.419(7) .
C21B C22B 1.440(8) .
C21B C29B 1.427(7) .
C22B C23B 1.408(7) .
C23B C24B 1.364(7) .
C23B C31B 1.451(8) .
C24B H24B 0.9500 .
C24B C25B 1.386(8) .
C25B H25B 0.9500 .
C26B H26B 0.9500 .
C26B C27B 1.393(8) .
C27B H27B 0.9500 .
C27B C28B 1.369(9) .
C28B H28B 0.9500 .
C28B C29B 1.399(8) .
C29B C30B 1.413(8) .
C30B H30B 0.9500 .
C30B C31B 1.325(8) .
C31B H31B 0.9500 .
C32 C33 1.5341(17) .
C32 C34 1.5367(19) .
C32 C35 1.5499(19) .
C33 H33A 0.9800 .
C33 H33B 0.9800 .
C33 H33C 0.9800 .
C34 H34A 0.9800 .
C34 H34B 0.9800 .
C34 H34C 0.9800 .
C35 H35A 0.9900 .
C35 H35B 0.9900 .
C35 C36 1.509(2) .
C36 H36A 0.9800 .
C36 H36B 0.9800 .
C36 H36C 0.9800 .
C1S_1 H1SA_1 0.9900 .
C1S_1 H1SB_1 0.9900 .
C1S_1 Cl2S_1 1.7623(18) .
C1S_1 Cl1S_1 1.777(2) .
C1S_2 H1SA_2 0.9900 .
C1S_2 H1SB_2 0.9900 .
C1S_2 Cl2S_2 1.760(9) .
C1S_2 Cl1S_2 1.772(9) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 177.92(11) . . . .
O1 C1 C2 C6 -3.03(18) . . . .
O3 C9 C10 C11 -175.48(11) . . . .
O3 C14 C15 C16A 71.46(14) . . . .
O3 C14 C15 C16B 71.46(14) . . . .
O4 C14 C15 C16A -109.29(15) . . . .
O4 C14 C15 C16B -109.29(15) . . . .
N1 C1 C2 C3 -2.87(16) . . . .
N1 C1 C2 C6 176.18(10) . . . .
N1 C8 C9 O3 -3.02(17) . . . .
N1 C8 C9 C10 -177.79(11) . . . .
N1 C8 C13 C12 178.81(11) . . . .
C1 N1 C5 O2 174.61(11) . . . .
C1 N1 C5 C4 -6.10(17) . . . .
C1 N1 C8 C9 -75.58(14) . . . .
C1 N1 C8 C13 105.57(13) . . . .
C1 C2 C3 C3 179.09(12) . . . 3_666
C1 C2 C3 C4 -1.21(16) . . . .
C1 C2 C6 C7 -178.64(11) . . . 3_666
C2 C3 C4 C5 1.90(17) . . . .
C2 C3 C4 C7 -179.78(11) . . . .
C3 C2 C6 C7 0.41(17) . . . 3_666
C3 C3 C4 C5 -178.39(12) 3_666 . . .
C3 C3 C4 C7 -0.1(2) 3_666 . . .
C3 C4 C5 O2 -179.25(11) . . . .
C3 C4 C5 N1 1.49(16) . . . .
C3 C4 C7 C6 -0.39(18) . . . 3_666
C5 N1 C1 O1 -173.99(11) . . . .
C5 N1 C1 C2 6.77(17) . . . .
C5 N1 C8 C9 98.78(13) . . . .
C5 N1 C8 C13 -80.06(14) . . . .
C5 C4 C7 C6 177.94(11) . . . 3_666
C6 C2 C3 C3 0.05(19) . . . 3_666
C6 C2 C3 C4 179.76(11) . . . .
C7 C4 C5 O2 2.41(18) . . . .
C7 C4 C5 N1 -176.85(11) . . . .
C8 N1 C1 O1 -0.19(17) . . . .
C8 N1 C1 C2 -179.43(10) . . . .
C8 N1 C5 O2 0.77(17) . . . .
C8 N1 C5 C4 -179.94(10) . . . .
C8 C9 C10 C11 -0.89(18) . . . .
C9 O3 C14 O4 0.34(18) . . . .
C9 O3 C14 C15 179.61(10) . . . .
C9 C8 C13 C12 -0.03(18) . . . .
C9 C10 C11 C12 -0.34(19) . . . .
C10 C11 C12 C13 1.33(18) . . . .
C10 C11 C12 C32 179.67(12) . . . .
C11 C12 C13 C8 -1.14(18) . . . .
C11 C12 C32 C33 5.89(18) . . . .
C11 C12 C32 C34 125.73(13) . . . .
C11 C12 C32 C35 -115.91(13) . . . .
C12 C32 C35 C36 57.59(15) . . . .
C13 C8 C9 O3 175.84(11) . . . .
C13 C8 C9 C10 1.07(18) . . . .
C13 C12 C32 C33 -175.80(12) . . . .
C13 C12 C32 C34 -55.96(16) . . . .
C13 C12 C32 C35 62.40(15) . . . .
C14 O3 C9 C8 114.10(12) . . . .
C14 O3 C9 C10 -71.19(15) . . . .
C14 C15 C16A C17A -90.6(11) . . . .
C14 C15 C16A C25A 92.4(3) . . . .
C14 C15 C16B C17B -90(3) . . . .
C14 C15 C16B C25B 88.4(10) . . . .
C15 C16A C17A C18A 3(2) . . . .
C15 C16A C17A C22A -175.9(9) . . . .
C15 C16A C25A C24A 177.4(3) . . . .
C15 C16B C17B C18B -1(7) . . . .
C15 C16B C17B C22B -177(4) . . . .
C15 C16B C25B C24B 177.1(11) . . . .
C16A C17A C18A C19A -178.0(12) . . . .
C16A C17A C22A C21A 177.3(10) . . . .
C16A C17A C22A C23A -1(2) . . . .
C17A C16A C25A C24A 0.3(12) . . . .
C17A C18A C19A C20A 0.4(13) . . . .
C17A C22A C23A C24A 0.0(12) . . . .
C17A C22A C23A C31A 177.6(11) . . . .
C18A C17A C22A C21A -2(2) . . . .
C18A C17A C22A C23A 179.6(11) . . . .
C18A C19A C20A C21A -1.3(5) . . . .
C18A C19A C20A C26A 177.2(4) . . . .
C19A C20A C21A C22A 0.5(4) . . . .
C19A C20A C21A C29A 178.6(2) . . . .
C19A C20A C26A C27A -179.0(2) . . . .
C20A C21A C22A C17A 1.2(11) . . . .
C20A C21A C22A C23A 179.5(3) . . . .
C20A C21A C29A C28A 0.4(3) . . . .
C20A C21A C29A C30A -178.76(19) . . . .
C20A C26A C27A C28A 0.6(3) . . . .
C21A C20A C26A C27A -0.6(3) . . . .
C21A C22A C23A C24A -178.3(3) . . . .
C21A C22A C23A C31A -0.7(5) . . . .
C21A C29A C30A C31A -0.9(3) . . . .
C22A C17A C18A C19A 1(2) . . . .
C22A C21A C29A C28A 178.5(3) . . . .
C22A C21A C29A C30A -0.6(4) . . . .
C22A C23A C24A C25A 1.2(5) . . . .
C22A C23A C31A C30A -0.8(4) . . . .
C23A C24A C25A C16A -1.4(6) . . . .
C24A C23A C31A C30A 176.7(2) . . . .
C25A C16A C17A C18A -179.8(12) . . . .
C25A C16A C17A C22A 1(2) . . . .
C26A C20A C21A C22A -178.0(3) . . . .
C26A C20A C21A C29A 0.1(3) . . . .
C26A C27A C28A C29A -0.1(3) . . . .
C27A C28A C29A C21A -0.4(3) . . . .
C27A C28A C29A C30A 178.73(19) . . . .
C28A C29A C30A C31A -180.0(2) . . . .
C29A C21A C22A C17A -176.9(11) . . . .
C29A C21A C22A C23A 1.4(5) . . . .
C29A C30A C31A C23A 1.6(3) . . . .
C31A C23A C24A C25A -176.3(3) . . . .
C16B C17B C18B C19B -174(4) . . . .
C16B C17B C22B C21B 173(4) . . . .
C16B C17B C22B C23B -2(7) . . . .
C17B C16B C25B C24B -5(4) . . . .
C17B C18B C19B C20B -1(4) . . . .
C17B C22B C23B C24B -1(4) . . . .
C17B C22B C23B C31B 177(3) . . . .
C18B C17B C22B C21B -3(7) . . . .
C18B C17B C22B C23B -178(3) . . . .
C18B C19B C20B C21B 1(2) . . . .
C18B C19B C20B C26B 178.9(15) . . . .
C19B C20B C21B C22B -1.4(15) . . . .
C19B C20B C21B C29B 177.4(8) . . . .
C19B C20B C26B C27B -177.0(8) . . . .
C20B C21B C22B C17B 3(4) . . . .
C20B C21B C22B C23B 178.4(11) . . . .
C20B C21B C29B C28B 0.3(13) . . . .
C20B C21B C29B C30B -178.4(8) . . . .
C20B C26B C27B C28B -1.0(12) . . . .
C21B C20B C26B C27B 1.4(12) . . . .
C21B C22B C23B C24B -177.1(12) . . . .
C21B C22B C23B C31B 1(2) . . . .
C21B C29B C30B C31B -1.2(13) . . . .
C22B C17B C18B C19B 2(7) . . . .
C22B C21B C29B C28B 179.1(11) . . . .
C22B C21B C29B C30B 0.4(14) . . . .
C22B C23B C24B C25B 2(2) . . . .
C22B C23B C31B C30B -1.9(16) . . . .
C23B C24B C25B C16B 1(2) . . . .
C24B C23B C31B C30B 176.4(10) . . . .
C25B C16B C17B C18B -179(4) . . . .
C25B C16B C17B C22B 5(7) . . . .
C26B C20B C21B C22B -179.9(10) . . . .
C26B C20B C21B C29B -1.1(13) . . . .
C26B C27B C28B C29B 0.2(13) . . . .
C27B C28B C29B C21B 0.2(13) . . . .
C27B C28B C29B C30B 178.9(8) . . . .
C28B C29B C30B C31B -179.9(8) . . . .
C29B C21B C22B C17B -176(4) . . . .
C29B C21B C22B C23B -0.5(19) . . . .
C29B C30B C31B C23B 1.9(13) . . . .
C31B C23B C24B C25B -176.6(13) . . . .
C32 C12 C13 C8 -179.55(11) . . . .
C33 C32 C35 C36 -65.80(15) . . . .
C34 C32 C35 C36 176.97(12) . . . .
