#------------------------------------------------------------------------------
#$Date: 2019-11-22 00:24:31 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231128 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/62/4516238.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_4516238
loop_
_publ_author_name
'Dos Santos, Paloma Lays'
'Chen, Dongyang'
'Rajamalli, Pachaiyappan'
'Matulaitis, Tomas'
'Cordes, David B.'
'Slawin, Alexandra M. Z.'
'Jacquemin, Denis'
'Zysman-Colman, Eli'
'Samuel, Ifor D. W.'
_publ_section_title
;
 The use of Pyrimidine and Pyrazine Bridges as a Design Strategy to
 Improve the Performance of Thermally Activated Delayed Fluorescence
 Organic Light Emitting Diodes.
;
_journal_name_full               'ACS applied materials & interfaces'
_journal_paper_doi               10.1021/acsami.9b16952
_journal_year                    2019
_chemical_formula_moiety         'C48 H52 N6 O2 S, C6 H5 Cl'
_chemical_formula_sum            'C54 H57 Cl N6 O2 S'
_chemical_formula_weight         889.60
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-08-13
_audit_creation_method           'by CrystalStructure 4.3'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   10.6650(3)
_cell_length_b                   36.1744(11)
_cell_length_c                   12.0287(4)
_cell_measurement_reflns_used    16379
_cell_measurement_temperature    173
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.25
_cell_volume                     4640.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            56955
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.084
_diffrn_reflns_theta_min         1.784
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888.00
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.91
_refine_diff_density_min         -1.19
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     354
_refine_ls_number_reflns         5644
_refine_ls_number_restraints     156
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.0857
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1783P)²+3.1376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2477
_refine_ls_wR_factor_ref         0.2822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3682
_reflns_number_total             5644
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            am9b16952_si_004.cif
_cod_data_source_block           pDTCz-DPzS
_cod_database_code               4516238
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,1/2-Z
3 -X,1/2+Y,-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,-1/2+Z
7 +X,-1/2-Y,+Z
8 -1/2+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_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
Cl31 Cl -0.6154(9) 0.250000 0.6809(10) 0.275(6) Uani 0.527(8) 2 d DS TU P A 1
Cl3A Cl -0.1263(7) 0.250000 0.6630(9) 0.165(4) Uani 0.473(8) 2 d DS TU P A 2
S1 S 0.09420(10) 0.250000 0.36407(10) 0.0380(3) Uani 1 2 d S T P B .
O1 O 0.0908(3) 0.250000 0.4832(3) 0.0529(10) Uani 1 2 d S T P . .
O2 O -0.0197(3) 0.250000 0.3007(3) 0.0525(9) Uani 1 2 d S T P . .
N1 N 0.1743(2) 0.19870(7) 0.2186(2) 0.0363(7) Uani 0.65(2) 1 d . . P B 1
N4 N 0.3634(3) 0.17484(8) 0.3583(2) 0.0381(7) Uani 0.65(2) 1 d . . P B 1
N1A N 0.2809(3) 0.20036(8) 0.3912(3) 0.0432(8) Uani 0.35(2) 1 d . . P B 2
N4A N 0.2556(2) 0.17268(8) 0.1830(2) 0.0360(7) Uani 0.35(2) 1 d . . P B 2
N7 N 0.4451(2) 0.13839(6) 0.21196(19) 0.0300(5) Uani 1 1 d . . . . .
C2 C 0.1897(3) 0.21226(7) 0.3211(3) 0.0325(6) Uani 1 1 d . . . . .
C5 C 0.3530(3) 0.16236(7) 0.2514(3) 0.0300(6) Uani 1 1 d . . . . .
C3 C 0.2809(3) 0.20036(8) 0.3912(3) 0.0432(8) Uani 0.65(2) 1 d . . P B 1
H3 H 0.286151 0.210269 0.464248 0.052 Uiso 0.65(2) 1 calc R U P B 1
C6 C 0.2556(2) 0.17268(8) 0.1830(2) 0.0360(7) Uani 0.65(2) 1 d . . P B 1
H6 H 0.245864 0.161668 0.111853 0.043 Uiso 0.65(2) 1 calc R U P B 1
C3A C 0.1743(2) 0.19870(7) 0.2186(2) 0.0363(7) Uani 0.35(2) 1 d . . P B 2
H3A H 0.108034 0.207121 0.172249 0.044 Uiso 0.35(2) 1 calc R U P B 2
C6A C 0.3634(3) 0.17484(8) 0.3583(2) 0.0381(7) Uani 0.35(2) 1 d . . P B 2
H6A H 0.426407 0.165748 0.406952 0.046 Uiso 0.35(2) 1 calc R U P B 2
C8 C 0.5129(2) 0.11213(7) 0.2750(2) 0.0295(6) Uani 1 1 d . . . . .
C9 C 0.5003(3) 0.10141(8) 0.3854(3) 0.0381(7) Uani 1 1 d . . . . .
H9 H 0.439092 0.112282 0.432572 0.046 Uiso 1 1 calc R U . . .
C10 C 0.5808(3) 0.07421(9) 0.4237(3) 0.0386(7) Uani 1 1 d . . . . .
H10 H 0.572945 0.066519 0.498904 0.046 Uiso 1 1 calc R U . . .
C11 C 0.6734(3) 0.05731(8) 0.3581(3) 0.0342(7) Uani 1 1 d . . . . .
C12 C 0.6828(3) 0.06852(7) 0.2475(3) 0.0323(6) Uani 1 1 d . . . . .
H12 H 0.743894 0.057557 0.200456 0.039 Uiso 1 1 calc R U . . .
C13 C 0.6031(2) 0.09571(7) 0.2055(2) 0.0283(6) Uani 1 1 d . . . . .
C14 C 0.5929(2) 0.11280(7) 0.0979(2) 0.0279(6) Uani 1 1 d . . . . .
C15 C 0.6626(3) 0.10897(8) 0.0000(2) 0.0318(6) Uani 1 1 d . . . . .
H15 H 0.725609 0.090467 -0.004802 0.038 Uiso 1 1 calc R U . . .
C16 C 0.6403(3) 0.13202(8) -0.0900(2) 0.0348(7) Uani 1 1 d . . . . .
C17 C 0.5449(3) 0.15871(9) -0.0799(2) 0.0354(7) Uani 1 1 d . . . . .
H17 H 0.529781 0.174827 -0.140762 0.042 Uiso 1 1 calc R U . . .
C18 C 0.4725(3) 0.16254(8) 0.0145(2) 0.0342(7) Uani 1 1 d . . . . .
H18 H 0.408326 0.180708 0.018381 0.041 Uiso 1 1 calc R U . . .
C19 C 0.4959(2) 0.13910(7) 0.1037(2) 0.0266(6) Uani 1 1 d . . . . .
C20 C 0.7597(3) 0.02798(9) 0.4086(3) 0.0416(8) Uani 1 1 d . . . . .
C21 C 0.8507(4) 0.01192(12) 0.3230(4) 0.0651(12) Uani 1 1 d . . . . .
H21A H 0.902873 0.031790 0.292597 0.078 Uiso 1 1 calc R U . . .
H21B H 0.803106 0.000271 0.262746 0.078 Uiso 1 1 calc R U . . .
H21C H 0.904267 -0.006576 0.358829 0.078 Uiso 1 1 calc R U . . .
C22 C 0.6799(4) -0.00347(10) 0.4564(4) 0.0580(10) Uani 1 1 d . . . . .
H22A H 0.631838 -0.015111 0.396480 0.070 Uiso 1 1 calc R U . . .
H22B H 0.622124 0.006501 0.512246 0.070 Uiso 1 1 calc R U . . .
H22C H 0.734717 -0.021890 0.491161 0.070 Uiso 1 1 calc R U . . .
C23 C 0.8357(4) 0.04534(13) 0.5027(4) 0.0716(13) Uani 1 1 d . . . . .
H23A H 0.778471 0.055054 0.559420 0.086 Uiso 1 1 calc R U . . .
H23B H 0.886979 0.065541 0.473105 0.086 Uiso 1 1 calc R U . . .
H23C H 0.890244 0.026578 0.536055 0.086 Uiso 1 1 calc R U . . .
C24 C 0.7235(3) 0.13179(11) -0.1939(3) 0.0513(9) Uani 1 1 d . . . . .
C25 C 0.8136(5) 0.16704(16) -0.1840(5) 0.0843(15) Uani 1 1 d . . . . .
H25A H 0.765168 0.188307 -0.157432 0.101 Uiso 1 1 calc R U . . .
H25B H 0.849401 0.172711 -0.257046 0.101 Uiso 1 1 calc R U . . .
H25C H 0.881344 0.161684 -0.131354 0.101 Uiso 1 1 calc R U . . .
C26 C 0.6552(4) 0.13667(18) -0.2994(3) 0.0824(16) Uani 1 1 d . . . . .
H26A H 0.596559 0.116101 -0.309709 0.099 Uiso 1 1 calc R U . . .
H26B H 0.715112 0.137125 -0.361230 0.099 Uiso 1 1 calc R U . . .
H26C H 0.608674 0.160010 -0.297529 0.099 Uiso 1 1 calc R U . . .
C27 C 0.8153(4) 0.10016(15) -0.1980(4) 0.0736(13) Uani 1 1 d . . . . .
H27A H 0.869770 0.102932 -0.263111 0.088 Uiso 1 1 calc R U . . .
H27B H 0.769421 0.076760 -0.203201 0.088 Uiso 1 1 calc R U . . .
H27C H 0.866519 0.100229 -0.130348 0.088 Uiso 1 1 calc R U . . .
C31 C -0.4521(11) 0.250000 0.6386(14) 0.123(5) Uani 0.527(8) 2 d DS TU P A 1
C32 C -0.3973(14) 0.250000 0.5364(14) 0.115(5) Uani 0.527(8) 2 d DS TU P A 1
H32 H -0.449907 0.250000 0.472702 0.138 Uiso 0.527(8) 2 calc R U P A 1
C33 C -0.2599(13) 0.250000 0.5198(11) 0.074(3) Uani 0.527(8) 2 d DS TU P A 1
H33 H -0.225615 0.250000 0.446880 0.089 Uiso 0.527(8) 2 calc R U P A 1
C34 C -0.1875(16) 0.250000 0.6051(16) 0.137(7) Uani 0.527(8) 2 d DS TU P A 1
H34 H -0.099193 0.250000 0.594791 0.164 Uiso 0.527(8) 2 calc R U P A 1
C35 C -0.2364(15) 0.250000 0.7122(13) 0.131(6) Uani 0.527(8) 2 d DS TU P A 1
H35 H -0.181074 0.250000 0.774101 0.157 Uiso 0.527(8) 2 calc R U P A 1
C36 C -0.3677(14) 0.250000 0.7303(15) 0.154(8) Uani 0.527(8) 2 d DS TU P A 1
H36 H -0.399585 0.250000 0.803995 0.184 Uiso 0.527(8) 2 calc R U P A 1
C31A C -0.2889(10) 0.250000 0.6347(11) 0.097(4) Uani 0.473(8) 2 d DS TU P A 2
C32A C -0.3369(13) 0.250000 0.5306(10) 0.100(6) Uani 0.473(8) 2 d DS TU P A 2
H32A H -0.280108 0.250000 0.469739 0.120 Uiso 0.473(8) 2 calc R U P A 2
C33A C -0.4669(15) 0.250000 0.5074(13) 0.115(6) Uani 0.473(8) 2 d DS TU P A 2
H33A H -0.497708 0.250000 0.433283 0.137 Uiso 0.473(8) 2 calc R U P A 2
C34A C -0.5458(14) 0.250000 0.5966(13) 0.118(6) Uani 0.473(8) 2 d DS TU P A 2
H34A H -0.633927 0.250000 0.585086 0.142 Uiso 0.473(8) 2 calc R U P A 2
C35A C -0.4956(12) 0.250000 0.7104(12) 0.084(4) Uani 0.473(8) 2 d DS TU P A 2
H35A H -0.550572 0.250000 0.772574 0.101 Uiso 0.473(8) 2 calc R U P A 2
C36A C -0.3716(11) 0.250000 0.7252(10) 0.065(3) Uani 0.473(8) 2 d DS TU P A 2
H36A H -0.338741 0.250000 0.798555 0.078 Uiso 0.473(8) 2 calc R U P A 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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(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
C31 Cl31 H35 158.6(15) . 2_456
C31A Cl3A H35A 147.3(11) . 2_556
O1 S1 O2 120.7(2) . .
O1 S1 C2 107.74(15) . 7_565
O2 S1 C2 109.30(14) . 7_565
O1 S1 C2 107.74(15) . .
O2 S1 C2 109.29(14) . .
C2 S1 C2 100.16(18) 7_565 .
C2 N1 C6 118.0(3) . .
C3 N4 C5 117.0(3) . .
C6A N1A C2 120.4(3) . .
C3A N4A C5 119.0(3) . .
C5 N7 C19 125.0(2) . .
C5 N7 C8 126.5(2) . .
C19 N7 C8 108.2(2) . .
N1 C2 C3 123.0(3) . .
C3A C2 N1A 123.0(3) . .
C3A C2 S1 118.6(2) . .
N1 C2 S1 118.6(2) . .
C3 C2 S1 118.2(2) . .
N1A C2 S1 118.2(2) . .
C6A C5 N4A 122.2(3) . .
N4 C5 C6 122.2(3) . .
C6A C5 N7 117.9(3) . .
N4 C5 N7 117.9(3) . .
N4A C5 N7 119.8(3) . .
C6 C5 N7 119.8(3) . .
N4 C3 C2 120.4(3) . .
N4 C3 H3 119.8 . .
C2 C3 H3 119.8 . .
N1 C6 C5 119.0(3) . .
N1 C6 H6 120.5 . .
C5 C6 H6 120.5 . .
C2 C3A N4A 118.0(3) . .
C2 C3A H3A 121.0 . .
N4A C3A H3A 121.0 . .
N1A C6A C5 117.0(3) . .
N1A C6A H6A 121.5 . .
C5 C6A H6A 121.5 . .
C9 C8 C13 121.1(3) . .
C9 C8 N7 130.6(3) . .
C13 C8 N7 108.3(2) . .
C10 C9 C8 117.1(3) . .
C10 C9 H9 121.4 . .
C8 C9 H9 121.4 . .
C9 C10 C11 124.0(3) . .
C9 C10 H10 118.0 . .
C11 C10 H10 118.0 . .
C12 C11 C10 117.4(3) . .
C12 C11 C20 122.5(3) . .
C10 C11 C20 120.1(3) . .
C13 C12 C11 120.4(3) . .
C13 C12 H12 119.8 . .
C11 C12 H12 119.8 . .
C12 C13 C8 120.0(3) . .
C12 C13 C14 132.5(3) . .
C8 C13 C14 107.5(2) . .
C15 C14 C19 119.9(3) . .
C15 C14 C13 132.4(3) . .
C19 C14 C13 107.6(2) . .
C16 C15 C14 120.4(3) . .
C16 C15 H15 119.8 . .
C14 C15 H15 119.8 . .
C15 C16 C17 118.0(3) . .
C15 C16 C24 122.3(3) . .
C17 C16 C24 119.5(3) . .
C18 C17 C16 123.0(3) . .
C18 C17 H17 118.5 . .
C16 C17 H17 118.5 . .
C17 C18 C19 118.2(3) . .
C17 C18 H18 120.9 . .
C19 C18 H18 120.9 . .
C18 C19 C14 120.4(2) . .
C18 C19 N7 130.9(2) . .
C14 C19 N7 108.4(2) . .
C23 C20 C21 108.6(3) . .
C23 C20 C11 109.1(3) . .
C21 C20 C11 112.2(3) . .
C23 C20 C22 108.8(3) . .
C21 C20 C22 108.9(3) . .
C11 C20 C22 109.2(3) . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C20 C22 H22A 109.5 . .
C20 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C20 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C20 C23 H23A 109.5 . .
C20 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C20 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C26 C24 C27 112.6(4) . .
C26 C24 C16 114.6(3) . .
C27 C24 C16 114.0(3) . .
C26 C24 C25 105.4(4) . .
C27 C24 C25 102.5(4) . .
C16 C24 C25 106.4(3) . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C24 C26 H26A 109.5 . .
C24 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C24 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C24 C27 H27A 109.5 . .
C24 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C24 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C32 C31 C36 115.4(10) . .
C32 C31 Cl31 131.7(12) . .
C36 C31 Cl31 112.9(10) . .
C31 C32 C33 123.2(12) . .
C31 C32 H32 118.4 . .
C33 C32 H32 118.4 . .
C34 C33 C32 119.2(12) . .
C34 C33 H33 120.4 . .
C32 C33 H33 120.4 . .
C33 C34 C35 121.0(13) . .
C33 C34 H34 119.5 . .
C35 C34 H34 119.5 . .
C34 C35 C36 120.8(13) . .
C34 C35 H35 119.6 . .
C36 C35 H35 119.6 . .
C35 C36 C31 120.4(13) . .
C35 C36 H36 119.8 . .
C31 C36 H36 119.8 . .
C32A C31A C36A 118.7(9) . .
C32A C31A Cl3A 123.3(10) . .
C36A C31A Cl3A 118.0(9) . .
C31A C32A C33A 123.6(11) . .
C31A C32A H32A 118.2 . .
C33A C32A H32A 118.2 . .
C34A C33A C32A 116.7(12) . .
C34A C33A H33A 121.6 . .
C32A C33A H33A 121.6 . .
C33A C34A C35A 120.5(12) . .
C33A C34A H34A 119.7 . .
C35A C34A H34A 119.7 . .
C36A C35A C34A 119.0(11) . .
C36A C35A H35A 120.5 . .
C34A C35A H35A 120.5 . .
C35A C36A C31A 121.4(11) . .
C35A C36A H36A 119.3 . .
C31A C36A H36A 119.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl31 C31 1.815(9) .
Cl31 H35 0.885(17) 2_456
Cl3A C31A 1.767(9) .
Cl3A H35A 1.119(16) 2_556
S1 O1 1.434(4) .
S1 O2 1.434(4) .
S1 C2 1.780(3) 7_565
S1 C2 1.780(3) .
N1 C2 1.337(4) .
N1 C6 1.350(4) .
N4 C3 1.335(4) .
N4 C5 1.367(4) .
N1A C6A 1.335(4) .
N1A C2 1.358(4) .
N4A C3A 1.350(4) .
N4A C5 1.376(4) .
N7 C5 1.394(3) .
N7 C19 1.411(3) .
N7 C8 1.414(4) .
C2 C3A 1.337(4) .
C2 C3 1.358(4) .
C5 C6A 1.367(4) .
C5 C6 1.376(4) .
C3 H3 0.9500 .
C6 H6 0.9500 .
C3A H3A 0.9500 .
C6A H6A 0.9500 .
C8 C9 1.389(4) .
C8 C13 1.407(4) .
C9 C10 1.385(4) .
C9 H9 0.9500 .
C10 C11 1.403(4) .
C10 H10 0.9500 .
C11 C12 1.395(4) .
C11 C20 1.531(4) .
C12 C13 1.394(4) .
C12 H12 0.9500 .
C13 C14 1.439(4) .
C14 C15 1.400(4) .
C14 C19 1.407(4) .
C15 C16 1.387(4) .
C15 H15 0.9500 .
C16 C17 1.408(4) .
C16 C24 1.534(4) .
C17 C18 1.380(4) .
C17 H17 0.9500 .
C18 C19 1.390(4) .
C18 H18 0.9500 .
C20 C23 1.527(5) .
C20 C21 1.529(5) .
C20 C22 1.533(5) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 C26 1.473(5) .
C24 C27 1.507(6) .
C24 C25 1.601(6) .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
C31 C32 1.360(14) .
C31 C36 1.423(15) .
C32 C33 1.479(14) .
C32 H32 0.9500 .
C33 C34 1.284(15) .
C33 H33 0.9500 .
C34 C35 1.390(15) .
C34 H34 0.9500 .
C35 C36 1.417(15) .
C35 H35 0.9500 .
C36 H36 0.9500 .
C31A C32A 1.353(13) .
C31A C36A 1.401(13) .
C32A C33A 1.414(14) .
C32A H32A 0.9500 .
C33A C34A 1.364(15) .
C33A H33A 0.9500 .
C34A C35A 1.471(15) .
C34A H34A 0.9500 .
C35A C36A 1.334(14) .
C35A H35A 0.9500 .
C36A H36A 0.9500 .
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
C6 N1 C2 C3 -1.8(4) .
C6 N1 C2 S1 173.3(2) .
C6A N1A C2 C3A 2.2(5) .
C6A N1A C2 S1 -172.9(2) .
O1 S1 C2 C3A 157.5(2) .
O2 S1 C2 C3A 24.8(3) .
C2 S1 C2 C3A -90.0(3) 7_565
O1 S1 C2 N1 157.5(2) .
O2 S1 C2 N1 24.8(3) .
C2 S1 C2 N1 -90.0(3) 7_565
O1 S1 C2 C3 -27.1(3) .
O2 S1 C2 C3 -159.9(2) .
C2 S1 C2 C3 85.4(3) 7_565
O1 S1 C2 N1A -27.1(3) .
O2 S1 C2 N1A -159.9(2) .
C2 S1 C2 N1A 85.4(3) 7_565
C3 N4 C5 C6 -6.0(4) .
C3 N4 C5 N7 174.0(3) .
C3A N4A C5 C6A 6.5(4) .
C3A N4A C5 N7 -173.5(2) .
C19 N7 C5 C6A -141.0(3) .
C8 N7 C5 C6A 31.8(4) .
C19 N7 C5 N4 -141.0(3) .
C8 N7 C5 N4 31.8(4) .
C19 N7 C5 N4A 39.0(4) .
C8 N7 C5 N4A -148.2(3) .
C19 N7 C5 C6 39.0(4) .
C8 N7 C5 C6 -148.2(3) .
C5 N4 C3 C2 1.7(4) .
N1 C2 C3 N4 2.2(5) .
S1 C2 C3 N4 -172.9(2) .
C2 N1 C6 C5 -2.5(4) .
N4 C5 C6 N1 6.5(4) .
N7 C5 C6 N1 -173.5(2) .
N1A C2 C3A N4A -1.8(4) .
S1 C2 C3A N4A 173.3(2) .
C5 N4A C3A C2 -2.5(4) .
C2 N1A C6A C5 1.7(4) .
N4A C5 C6A N1A -6.0(4) .
N7 C5 C6A N1A 174.0(3) .
C5 N7 C8 C9 5.6(5) .
C19 N7 C8 C9 179.4(3) .
C5 N7 C8 C13 -175.6(2) .
C19 N7 C8 C13 -1.7(3) .
C13 C8 C9 C10 0.5(4) .
N7 C8 C9 C10 179.2(3) .
C8 C9 C10 C11 0.3(5) .
C9 C10 C11 C12 -0.8(5) .
C9 C10 C11 C20 178.8(3) .
C10 C11 C12 C13 0.5(4) .
C20 C11 C12 C13 -179.2(3) .
C11 C12 C13 C8 0.3(4) .
C11 C12 C13 C14 178.8(3) .
C9 C8 C13 C12 -0.8(4) .
N7 C8 C13 C12 -179.8(2) .
C9 C8 C13 C14 -179.7(3) .
N7 C8 C13 C14 1.4(3) .
C12 C13 C14 C15 -2.9(5) .
C8 C13 C14 C15 175.8(3) .
C12 C13 C14 C19 -179.2(3) .
C8 C13 C14 C19 -0.5(3) .
C19 C14 C15 C16 2.7(4) .
C13 C14 C15 C16 -173.1(3) .
C14 C15 C16 C17 -0.9(4) .
C14 C15 C16 C24 173.1(3) .
C15 C16 C17 C18 -0.8(4) .
C24 C16 C17 C18 -175.0(3) .
C16 C17 C18 C19 0.6(4) .
C17 C18 C19 C14 1.3(4) .
C17 C18 C19 N7 174.3(3) .
C15 C14 C19 C18 -3.0(4) .
C13 C14 C19 C18 173.8(2) .
C15 C14 C19 N7 -177.4(2) .
C13 C14 C19 N7 -0.6(3) .
C5 N7 C19 C18 1.8(5) .
C8 N7 C19 C18 -172.2(3) .
C5 N7 C19 C14 175.4(2) .
C8 N7 C19 C14 1.4(3) .
C12 C11 C20 C23 118.0(4) .
C10 C11 C20 C23 -61.7(4) .
C12 C11 C20 C21 -2.5(4) .
C10 C11 C20 C21 177.9(3) .
C12 C11 C20 C22 -123.3(3) .
C10 C11 C20 C22 57.1(4) .
C15 C16 C24 C26 142.1(4) .
C17 C16 C24 C26 -44.0(5) .
C15 C16 C24 C27 10.4(5) .
C17 C16 C24 C27 -175.7(3) .
C15 C16 C24 C25 -101.9(4) .
C17 C16 C24 C25 72.0(4) .
C36 C31 C32 C33 0.000(3) .
Cl31 C31 C32 C33 180.000(3) .
C31 C32 C33 C34 0.000(6) .
C32 C33 C34 C35 0.000(3) .
C33 C34 C35 C36 0.000(4) .
C34 C35 C36 C31 0.000(4) .
C32 C31 C36 C35 0.000(3) .
Cl31 C31 C36 C35 180.000(3) .
C36A C31A C32A C33A 0.000(3) .
Cl3A C31A C32A C33A 180.000(2) .
C31A C32A C33A C34A 0.000(4) .
C32A C33A C34A C35A 0.000(3) .
C33A C34A C35A C36A 0.000(3) .
C34A C35A C36A C31A 0.000(3) .
C32A C31A C36A C35A 0.000(3) .
Cl3A C31A C36A C35A 180.000(3) .
