#------------------------------------------------------------------------------
#$Date: 2017-02-17 08:57:54 +0200 (Fri, 17 Feb 2017) $
#$Revision: 192220 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/91/7119129.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_7119129
loop_
_publ_author_name
'Hongxu Liu'
'Yanyan Yang'
'Jie Wu'
'Xiao-Na Wang'
'Junbiao Chang'
_publ_section_title
;
 Regioselective synthesis of 3,4-disubstituted isocoumarins through the
 Pd-catalyzed annulation of 2-iodoaromatic acids with ynamides
;
_journal_name_full               Chem.Commun.
_journal_page_first              6801
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C30 H25 N O4 S'
_chemical_formula_weight         495.57
_chemical_name_systematic
N-benzyl-4-methyl-N-(1-oxo-4-(p-tolyl)-1H-isochromen-3-yl)benzenesulfonamide
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-02-20 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                71.7040(10)
_cell_angle_beta                 82.1800(10)
_cell_angle_gamma                66.1200(10)
_cell_formula_units_Z            4
_cell_length_a                   12.2963(4)
_cell_length_b                   13.8393(4)
_cell_length_c                   16.8203(4)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.14
_cell_measurement_theta_min      2.38
_cell_volume                     2484.87(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        "'Bruker SAINT"
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            61154
_diffrn_reflns_theta_full        25.44
_diffrn_reflns_theta_max         25.44
_diffrn_reflns_theta_min         1.28
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.9753
_exptl_absorpt_correction_T_min  0.9624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/ethyl acetate'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       0.049(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     650
_refine_ls_number_reflns         9162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0956P)²+0.4412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1665
_reflns_number_gt                6646
_reflns_number_total             9162
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc01565d2.cif
_cod_data_source_block           a
_cod_original_cell_volume        2484.87(12)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7119129
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8297(2) 0.3478(2) 0.44606(14) 0.0512(6) Uani 1 1 d . . .
C2 C 0.8319(3) 0.4456(2) 0.44964(17) 0.0645(7) Uani 1 1 d . . .
H2A H 0.7715 0.4906 0.4770 0.077 Uiso 1 1 calc R . .
C3 C 0.9255(3) 0.4753(3) 0.4118(2) 0.0780(9) Uani 1 1 d . . .
H3A H 0.9276 0.5404 0.4149 0.094 Uiso 1 1 calc R . .
C4 C 1.0149(3) 0.4118(3) 0.36979(19) 0.0730(8) Uani 1 1 d . . .
C5 C 1.0110(3) 0.3143(3) 0.36741(18) 0.0708(8) Uani 1 1 d . . .
H5A H 1.0717 0.2696 0.3399 0.085 Uiso 1 1 calc R . .
C6 C 0.9196(2) 0.2814(2) 0.40472(16) 0.0598(6) Uani 1 1 d . . .
H6A H 0.9184 0.2157 0.4021 0.072 Uiso 1 1 calc R . .
C7 C 1.1139(3) 0.4472(4) 0.3264(2) 0.1106(13) Uani 1 1 d . . .
H7A H 1.1031 0.5159 0.3351 0.166 Uiso 1 1 calc R . .
H7B H 1.1127 0.4563 0.2675 0.166 Uiso 1 1 calc R . .
H7C H 1.1889 0.3920 0.3491 0.166 Uiso 1 1 calc R . .
C8 C 0.5658(2) 0.44964(19) 0.37156(16) 0.0564(6) Uani 1 1 d . . .
H8A H 0.6137 0.4915 0.3691 0.068 Uiso 1 1 calc R . .
H8B H 0.4965 0.4748 0.4063 0.068 Uiso 1 1 calc R . .
C9 C 0.5262(2) 0.47167(18) 0.28511(15) 0.0486(5) Uani 1 1 d . . .
C10 C 0.4067(2) 0.5134(2) 0.26785(18) 0.0648(7) Uani 1 1 d . . .
H10A H 0.3512 0.5225 0.3111 0.078 Uiso 1 1 calc R . .
C11 C 0.3687(3) 0.5417(3) 0.1879(2) 0.0859(10) Uani 1 1 d . . .
H11A H 0.2877 0.5704 0.1773 0.103 Uiso 1 1 calc R . .
C12 C 0.4474(4) 0.5282(3) 0.1245(2) 0.0912(10) Uani 1 1 d . . .
H12A H 0.4206 0.5484 0.0703 0.109 Uiso 1 1 calc R . .
C13 C 0.5676(4) 0.4846(3) 0.1396(2) 0.0867(10) Uani 1 1 d . . .
H13A H 0.6222 0.4738 0.0961 0.104 Uiso 1 1 calc R . .
C14 C 0.6065(2) 0.4569(2) 0.22039(18) 0.0656(7) Uani 1 1 d . . .
H14A H 0.6875 0.4282 0.2308 0.079 Uiso 1 1 calc R . .
C15 C 0.3881(2) 0.2447(2) 0.46186(16) 0.0612(7) Uani 1 1 d . . .
C16 C 0.4260(2) 0.1534(2) 0.42567(15) 0.0555(6) Uani 1 1 d . . .
C17 C 0.3466(3) 0.1035(3) 0.42727(19) 0.0728(8) Uani 1 1 d . . .
H17A H 0.2714 0.1287 0.4513 0.087 Uiso 1 1 calc R . .
C18 C 0.3794(3) 0.0180(3) 0.3936(2) 0.0809(9) Uani 1 1 d . . .
H18A H 0.3266 -0.0153 0.3947 0.097 Uiso 1 1 calc R . .
C19 C 0.4913(3) -0.0196(3) 0.3575(2) 0.0773(8) Uani 1 1 d . . .
H19A H 0.5130 -0.0777 0.3343 0.093 Uiso 1 1 calc R . .
C20 C 0.5710(2) 0.0286(2) 0.35559(17) 0.0621(7) Uani 1 1 d . . .
H20A H 0.6460 0.0024 0.3316 0.075 Uiso 1 1 calc R . .
C21 C 0.53928(19) 0.11656(19) 0.38952(14) 0.0493(5) Uani 1 1 d . . .
C22 C 0.61860(18) 0.17228(18) 0.38651(14) 0.0452(5) Uani 1 1 d . . .
C23 C 0.57747(18) 0.25929(19) 0.41624(14) 0.0473(5) Uani 1 1 d . . .
C24 C 0.74175(18) 0.13237(17) 0.35189(14) 0.0435(5) Uani 1 1 d . . .
C25 C 0.7667(2) 0.1699(2) 0.26789(15) 0.0566(6) Uani 1 1 d . . .
H25A H 0.7054 0.2197 0.2311 0.068 Uiso 1 1 calc R . .
C26 C 0.8835(2) 0.1335(2) 0.23807(17) 0.0625(7) Uani 1 1 d . . .
H26A H 0.8990 0.1596 0.1814 0.075 Uiso 1 1 calc R . .
C27 C 0.9766(2) 0.0595(2) 0.29079(17) 0.0548(6) Uani 1 1 d . . .
C28 C 0.9503(2) 0.0190(2) 0.37360(17) 0.0556(6) Uani 1 1 d . . .
H28A H 1.0113 -0.0330 0.4099 0.067 Uiso 1 1 calc R . .
C29 C 0.83499(19) 0.05416(19) 0.40375(15) 0.0500(6) Uani 1 1 d . . .
H29A H 0.8196 0.0249 0.4599 0.060 Uiso 1 1 calc R . .
C30 C 1.1038(2) 0.0239(3) 0.2597(2) 0.0834(9) Uani 1 1 d . . .
H30A H 1.1556 -0.0272 0.3053 0.125 Uiso 1 1 calc R . .
H30B H 1.1244 0.0872 0.2372 0.125 Uiso 1 1 calc R . .
H30C H 1.1124 -0.0110 0.2168 0.125 Uiso 1 1 calc R . .
C31 C 0.3274(3) -0.0509(2) 0.96106(16) 0.0644(7) Uani 1 1 d . . .
C32 C 0.3203(3) -0.1497(3) 0.96302(19) 0.0805(9) Uani 1 1 d . . .
H32A H 0.2603 -0.1704 0.9935 0.097 Uiso 1 1 calc R . .
C33 C 0.4033(4) -0.2159(3) 0.9191(2) 0.0887(10) Uani 1 1 d . . .
H33A H 0.3988 -0.2819 0.9203 0.106 Uiso 1 1 calc R . .
C34 C 0.4934(3) -0.1870(3) 0.8732(2) 0.0802(9) Uani 1 1 d . . .
C35 C 0.4999(3) -0.0904(3) 0.8746(2) 0.0799(9) Uani 1 1 d . . .
H35A H 0.5614 -0.0709 0.8457 0.096 Uiso 1 1 calc R . .
C36 C 0.4182(3) -0.0223(3) 0.91753(19) 0.0729(8) Uani 1 1 d . . .
H36A H 0.4242 0.0427 0.9172 0.087 Uiso 1 1 calc R . .
C37 C 0.5786(3) -0.2575(3) 0.8216(3) 0.1115(13) Uani 1 1 d . . .
H37A H 0.6347 -0.2253 0.7939 0.167 Uiso 1 1 calc R . .
H37B H 0.5353 -0.2621 0.7805 0.167 Uiso 1 1 calc R . .
H37C H 0.6203 -0.3301 0.8573 0.167 Uiso 1 1 calc R . .
C38 C 0.0650(2) 0.0938(2) 0.88962(15) 0.0636(7) Uani 1 1 d . . .
H38A H -0.0118 0.1074 0.9178 0.076 Uiso 1 1 calc R . .
H38B H 0.1051 0.0150 0.8977 0.076 Uiso 1 1 calc R . .
C39 C 0.0471(2) 0.1518(2) 0.79811(14) 0.0505(6) Uani 1 1 d . . .
C40 C 0.1427(2) 0.1429(2) 0.74379(15) 0.0591(6) Uani 1 1 d . . .
H40A H 0.2193 0.1019 0.7647 0.071 Uiso 1 1 calc R . .
C41 C 0.1275(3) 0.1932(2) 0.65949(16) 0.0650(7) Uani 1 1 d . . .
H41A H 0.1932 0.1871 0.6238 0.078 Uiso 1 1 calc R . .
C42 C 0.0152(3) 0.2523(2) 0.62820(18) 0.0739(8) Uani 1 1 d . . .
H42A H 0.0042 0.2863 0.5710 0.089 Uiso 1 1 calc R . .
C43 C -0.0811(3) 0.2614(3) 0.6811(2) 0.0804(9) Uani 1 1 d . . .
H43A H -0.1575 0.3014 0.6597 0.096 Uiso 1 1 calc R . .
C44 C -0.0654(2) 0.2118(2) 0.76563(18) 0.0666(7) Uani 1 1 d . . .
H44A H -0.1314 0.2188 0.8012 0.080 Uiso 1 1 calc R . .
C45 C -0.1068(2) 0.3657(3) 0.97037(17) 0.0711(8) Uani 1 1 d . . .
C46 C -0.0679(2) 0.4558(3) 0.92989(16) 0.0626(7) Uani 1 1 d . . .
C47 C -0.1428(3) 0.5618(3) 0.93144(19) 0.0804(9) Uani 1 1 d . . .
H47A H -0.2163 0.5738 0.9585 0.096 Uiso 1 1 calc R . .
C48 C -0.1095(3) 0.6489(3) 0.8936(2) 0.0867(10) Uani 1 1 d . . .
H48A H -0.1603 0.7197 0.8948 0.104 Uiso 1 1 calc R . .
C49 C 0.0009(3) 0.6310(3) 0.85309(19) 0.0806(9) Uani 1 1 d . . .
H49A H 0.0236 0.6901 0.8271 0.097 Uiso 1 1 calc R . .
C50 C 0.0762(3) 0.5259(2) 0.85163(17) 0.0666(7) Uani 1 1 d . . .
H50A H 0.1494 0.5146 0.8243 0.080 Uiso 1 1 calc R . .
C51 C 0.0439(2) 0.4364(2) 0.89067(14) 0.0565(6) Uani 1 1 d . . .
C52 C 0.1207(2) 0.3241(2) 0.89086(14) 0.0508(6) Uani 1 1 d . . .
C53 C 0.0810(2) 0.2438(2) 0.92773(14) 0.0560(6) Uani 1 1 d . . .
C54 C 0.2415(2) 0.3001(2) 0.85086(14) 0.0482(5) Uani 1 1 d . . .
C55 C 0.2580(2) 0.3104(2) 0.76615(15) 0.0571(6) Uani 1 1 d . . .
H55A H 0.1925 0.3347 0.7326 0.069 Uiso 1 1 calc R . .
C56 C 0.3703(2) 0.2850(2) 0.73082(16) 0.0631(7) Uani 1 1 d . . .
H56A H 0.3794 0.2918 0.6738 0.076 Uiso 1 1 calc R . .
C57 C 0.4693(2) 0.2499(2) 0.77827(18) 0.0594(7) Uani 1 1 d . . .
C58 C 0.4517(2) 0.2449(2) 0.86158(18) 0.0623(7) Uani 1 1 d . . .
H58A H 0.5168 0.2246 0.8943 0.075 Uiso 1 1 calc R . .
C59 C 0.3400(2) 0.2693(2) 0.89796(15) 0.0573(6) Uani 1 1 d . . .
H59A H 0.3309 0.2649 0.9546 0.069 Uiso 1 1 calc R . .
C60 C 0.5930(3) 0.2170(3) 0.7402(2) 0.0931(11) Uani 1 1 d . . .
H60A H 0.5880 0.2252 0.6818 0.140 Uiso 1 1 calc R . .
H60B H 0.6395 0.1415 0.7683 0.140 Uiso 1 1 calc R . .
H60C H 0.6301 0.2634 0.7463 0.140 Uiso 1 1 calc R . .
N1 N 0.63617(16) 0.33060(15) 0.41077(12) 0.0473(5) Uani 1 1 d . . .
N2 N 0.13714(18) 0.13290(19) 0.92719(12) 0.0558(5) Uani 1 1 d . . .
O1 O 0.64648(17) 0.37823(16) 0.54336(11) 0.0715(5) Uani 1 1 d . . .
O2 O 0.75797(15) 0.19037(14) 0.53221(10) 0.0591(4) Uani 1 1 d . . .
O3 O 0.29578(16) 0.28173(19) 0.49685(14) 0.0882(7) Uani 1 1 d . . .
O4 O 0.46701(13) 0.29471(14) 0.45416(11) 0.0587(4) Uani 1 1 d . . .
O5 O 0.1492(2) -0.0181(2) 1.06339(11) 0.0916(7) Uani 1 1 d . . .
O6 O 0.26437(18) 0.09711(18) 1.04359(11) 0.0747(6) Uani 1 1 d . . .
O7 O -0.20015(18) 0.3723(2) 1.00624(15) 0.1007(8) Uani 1 1 d . . .
O8 O -0.02856(16) 0.26255(18) 0.96784(11) 0.0702(5) Uani 1 1 d . . .
S1 S 0.71370(5) 0.30652(5) 0.49392(4) 0.05115(19) Uani 1 1 d . . .
S2 S 0.21648(7) 0.04021(7) 1.00994(4) 0.0667(2) Uani 1 1 d . . .
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'
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
C2 C1 C6 120.2(3) . .
C2 C1 S1 120.4(2) . .
C6 C1 S1 119.34(19) . .
C3 C2 C1 118.9(3) . .
C3 C2 H2A 120.5 . .
C1 C2 H2A 120.5 . .
C4 C3 C2 122.1(3) . .
C4 C3 H3A 119.0 . .
C2 C3 H3A 119.0 . .
C3 C4 C5 117.9(3) . .
C3 C4 C7 121.4(3) . .
C5 C4 C7 120.7(3) . .
C6 C5 C4 121.8(3) . .
C6 C5 H5A 119.1 . .
C4 C5 H5A 119.1 . .
C5 C6 C1 119.0(3) . .
C5 C6 H6A 120.5 . .
C1 C6 H6A 120.5 . .
C4 C7 H7A 109.5 . .
C4 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C4 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N1 C8 C9 112.46(19) . .
N1 C8 H8A 109.1 . .
C9 C8 H8A 109.1 . .
N1 C8 H8B 109.1 . .
C9 C8 H8B 109.1 . .
H8A C8 H8B 107.8 . .
C14 C9 C10 118.4(2) . .
C14 C9 C8 121.3(2) . .
C10 C9 C8 120.2(2) . .
C11 C10 C9 120.9(3) . .
C11 C10 H10A 119.5 . .
C9 C10 H10A 119.5 . .
C12 C11 C10 120.6(3) . .
C12 C11 H11A 119.7 . .
C10 C11 H11A 119.7 . .
C11 C12 C13 120.1(3) . .
C11 C12 H12A 119.9 . .
C13 C12 H12A 119.9 . .
C12 C13 C14 119.5(3) . .
C12 C13 H13A 120.2 . .
C14 C13 H13A 120.2 . .
C9 C14 C13 120.5(3) . .
C9 C14 H14A 119.8 . .
C13 C14 H14A 119.8 . .
O3 C15 O4 116.5(3) . .
O3 C15 C16 127.4(3) . .
O4 C15 C16 116.0(2) . .
C17 C16 C21 120.7(3) . .
C17 C16 C15 118.6(2) . .
C21 C16 C15 120.7(2) . .
C18 C17 C16 120.0(3) . .
C18 C17 H17A 120.0 . .
C16 C17 H17A 120.0 . .
C17 C18 C19 120.1(3) . .
C17 C18 H18A 119.9 . .
C19 C18 H18A 119.9 . .
C20 C19 C18 120.6(3) . .
C20 C19 H19A 119.7 . .
C18 C19 H19A 119.7 . .
C19 C20 C21 120.3(3) . .
C19 C20 H20A 119.8 . .
C21 C20 H20A 119.8 . .
C20 C21 C16 118.3(2) . .
C20 C21 C22 122.3(2) . .
C16 C21 C22 119.4(2) . .
C23 C22 C21 117.6(2) . .
C23 C22 C24 121.4(2) . .
C21 C22 C24 120.92(19) . .
C22 C23 O4 123.5(2) . .
C22 C23 N1 125.8(2) . .
O4 C23 N1 110.68(18) . .
C25 C24 C29 117.9(2) . .
C25 C24 C22 121.8(2) . .
C29 C24 C22 120.3(2) . .
C24 C25 C26 120.3(2) . .
C24 C25 H25A 119.9 . .
C26 C25 H25A 119.9 . .
C27 C26 C25 121.4(2) . .
C27 C26 H26A 119.3 . .
C25 C26 H26A 119.3 . .
C28 C27 C26 117.9(2) . .
C28 C27 C30 120.4(2) . .
C26 C27 C30 121.7(3) . .
C27 C28 C29 121.1(2) . .
C27 C28 H28A 119.4 . .
C29 C28 H28A 119.4 . .
C28 C29 C24 121.2(2) . .
C28 C29 H29A 119.4 . .
C24 C29 H29A 119.4 . .
C27 C30 H30A 109.5 . .
C27 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
C27 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
C36 C31 C32 120.1(3) . .
C36 C31 S2 119.8(2) . .
C32 C31 S2 120.0(3) . .
C33 C32 C31 119.0(3) . .
C33 C32 H32A 120.5 . .
C31 C32 H32A 120.5 . .
C32 C33 C34 121.7(3) . .
C32 C33 H33A 119.2 . .
C34 C33 H33A 119.2 . .
C35 C34 C33 117.9(3) . .
C35 C34 C37 121.5(4) . .
C33 C34 C37 120.6(3) . .
C36 C35 C34 121.8(3) . .
C36 C35 H35A 119.1 . .
C34 C35 H35A 119.1 . .
C35 C36 C31 119.5(3) . .
C35 C36 H36A 120.2 . .
C31 C36 H36A 120.2 . .
C34 C37 H37A 109.5 . .
C34 C37 H37B 109.5 . .
H37A C37 H37B 109.5 . .
C34 C37 H37C 109.5 . .
H37A C37 H37C 109.5 . .
H37B C37 H37C 109.5 . .
N2 C38 C39 111.0(2) . .
N2 C38 H38A 109.4 . .
C39 C38 H38A 109.4 . .
N2 C38 H38B 109.4 . .
C39 C38 H38B 109.4 . .
H38A C38 H38B 108.0 . .
C44 C39 C40 118.3(2) . .
C44 C39 C38 120.9(2) . .
C40 C39 C38 120.7(2) . .
C41 C40 C39 121.3(2) . .
C41 C40 H40A 119.3 . .
C39 C40 H40A 119.3 . .
C42 C41 C40 119.6(3) . .
C42 C41 H41A 120.2 . .
C40 C41 H41A 120.2 . .
C41 C42 C43 119.9(3) . .
C41 C42 H42A 120.0 . .
C43 C42 H42A 120.0 . .
C42 C43 C44 120.3(3) . .
C42 C43 H43A 119.8 . .
C44 C43 H43A 119.8 . .
C43 C44 C39 120.5(3) . .
C43 C44 H44A 119.8 . .
C39 C44 H44A 119.8 . .
O7 C45 O8 116.9(3) . .
O7 C45 C46 126.7(3) . .
O8 C45 C46 116.4(2) . .
C47 C46 C51 120.3(3) . .
C47 C46 C45 118.9(3) . .
C51 C46 C45 120.9(3) . .
C48 C47 C46 120.6(3) . .
C48 C47 H47A 119.7 . .
C46 C47 H47A 119.7 . .
C47 C48 C49 119.8(3) . .
C47 C48 H48A 120.1 . .
C49 C48 H48A 120.1 . .
C50 C49 C48 120.0(3) . .
C50 C49 H49A 120.0 . .
C48 C49 H49A 120.0 . .
C49 C50 C51 120.8(3) . .
C49 C50 H50A 119.6 . .
C51 C50 H50A 119.6 . .
C50 C51 C46 118.5(3) . .
C50 C51 C52 122.6(2) . .
C46 C51 C52 118.9(2) . .
C53 C52 C51 118.4(2) . .
C53 C52 C54 121.3(2) . .
C51 C52 C54 120.3(2) . .
C52 C53 O8 122.8(3) . .
C52 C53 N2 126.5(2) . .
O8 C53 N2 110.6(2) . .
C59 C54 C55 118.0(2) . .
C59 C54 C52 120.4(2) . .
C55 C54 C52 121.6(2) . .
C56 C55 C54 120.8(2) . .
C56 C55 H55A 119.6 . .
C54 C55 H55A 119.6 . .
C57 C56 C55 121.3(2) . .
C57 C56 H56A 119.3 . .
C55 C56 H56A 119.3 . .
C58 C57 C56 117.5(2) . .
C58 C57 C60 121.2(3) . .
C56 C57 C60 121.3(3) . .
C57 C58 C59 121.8(2) . .
C57 C58 H58A 119.1 . .
C59 C58 H58A 119.1 . .
C58 C59 C54 120.5(2) . .
C58 C59 H59A 119.8 . .
C54 C59 H59A 119.8 . .
C57 C60 H60A 109.5 . .
C57 C60 H60B 109.5 . .
H60A C60 H60B 109.5 . .
C57 C60 H60C 109.5 . .
H60A C60 H60C 109.5 . .
H60B C60 H60C 109.5 . .
C23 N1 C8 115.02(18) . .
C23 N1 S1 117.25(15) . .
C8 N1 S1 113.76(15) . .
C53 N2 C38 114.4(2) . .
C53 N2 S2 118.78(15) . .
C38 N2 S2 114.67(18) . .
C15 O4 C23 122.55(19) . .
C45 O8 C53 122.7(2) . .
O1 S1 O2 118.97(11) . .
O1 S1 N1 110.64(10) . .
O2 S1 N1 106.49(10) . .
O1 S1 C1 107.50(12) . .
O2 S1 C1 110.52(11) . .
N1 S1 C1 101.32(10) . .
O5 S2 O6 118.95(12) . .
O5 S2 N2 110.71(12) . .
O6 S2 N2 106.15(12) . .
O5 S2 C31 107.75(15) . .
O6 S2 C31 111.32(13) . .
N2 S2 C31 100.39(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.385(4) .
C1 C6 1.385(3) .
C1 S1 1.752(3) .
C2 C3 1.384(4) .
C2 H2A 0.9300 .
C3 C4 1.370(4) .
C3 H3A 0.9300 .
C4 C5 1.383(4) .
C4 C7 1.506(4) .
C5 C6 1.381(4) .
C5 H5A 0.9300 .
C6 H6A 0.9300 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 N1 1.489(3) .
C8 C9 1.496(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C14 1.373(3) .
C9 C10 1.379(3) .
C10 C11 1.369(4) .
C10 H10A 0.9300 .
C11 C12 1.344(5) .
C11 H11A 0.9300 .
C12 C13 1.377(5) .
C12 H12A 0.9300 .
C13 C14 1.386(4) .
C13 H13A 0.9300 .
C14 H14A 0.9300 .
C15 O3 1.197(3) .
C15 O4 1.375(3) .
C15 C16 1.455(4) .
C16 C17 1.399(4) .
C16 C21 1.399(3) .
C17 C18 1.363(5) .
C17 H17A 0.9300 .
C18 C19 1.387(4) .
C18 H18A 0.9300 .
C19 C20 1.383(4) .
C19 H19A 0.9300 .
C20 C21 1.396(3) .
C20 H20A 0.9300 .
C21 C22 1.456(3) .
C22 C23 1.331(3) .
C22 C24 1.491(3) .
C23 O4 1.383(2) .
C23 N1 1.416(3) .
C24 C25 1.382(3) .
C24 C29 1.386(3) .
C25 C26 1.395(3) .
C25 H25A 0.9300 .
C26 C27 1.379(4) .
C26 H26A 0.9300 .
C27 C28 1.376(4) .
C27 C30 1.510(3) .
C28 C29 1.381(3) .
C28 H28A 0.9300 .
C29 H29A 0.9300 .
C30 H30A 0.9600 .
C30 H30B 0.9600 .
C30 H30C 0.9600 .
C31 C36 1.376(4) .
C31 C32 1.394(4) .
C31 S2 1.755(3) .
C32 C33 1.374(5) .
C32 H32A 0.9300 .
C33 C34 1.385(5) .
C33 H33A 0.9300 .
C34 C35 1.379(4) .
C34 C37 1.504(5) .
C35 C36 1.371(4) .
C35 H35A 0.9300 .
C36 H36A 0.9300 .
C37 H37A 0.9600 .
C37 H37B 0.9600 .
C37 H37C 0.9600 .
C38 N2 1.495(3) .
C38 C39 1.495(3) .
C38 H38A 0.9700 .
C38 H38B 0.9700 .
C39 C44 1.375(3) .
C39 C40 1.377(3) .
C40 C41 1.370(4) .
C40 H40A 0.9300 .
C41 C42 1.366(4) .
C41 H41A 0.9300 .
C42 C43 1.368(4) .
C42 H42A 0.9300 .
C43 C44 1.373(4) .
C43 H43A 0.9300 .
C44 H44A 0.9300 .
C45 O7 1.204(3) .
C45 O8 1.371(4) .
C45 C46 1.452(4) .
C46 C47 1.388(4) .
C46 C51 1.401(3) .
C47 C48 1.368(5) .
C47 H47A 0.9300 .
C48 C49 1.396(5) .
C48 H48A 0.9300 .
C49 C50 1.379(4) .
C49 H49A 0.9300 .
C50 C51 1.393(4) .
C50 H50A 0.9300 .
C51 C52 1.455(4) .
C52 C53 1.335(3) .
C52 C54 1.496(3) .
C53 O8 1.384(3) .
C53 N2 1.408(3) .
C54 C59 1.381(3) .
C54 C55 1.382(3) .
C55 C56 1.378(3) .
C55 H55A 0.9300 .
C56 C57 1.378(4) .
C56 H56A 0.9300 .
C57 C58 1.373(4) .
C57 C60 1.513(3) .
C58 C59 1.378(3) .
C58 H58A 0.9300 .
C59 H59A 0.9300 .
C60 H60A 0.9600 .
C60 H60B 0.9600 .
C60 H60C 0.9600 .
N1 S1 1.6700(19) .
N2 S2 1.664(2) .
O1 S1 1.4237(17) .
O2 S1 1.4255(18) .
O5 S2 1.4237(19) .
O6 S2 1.4259(18) .
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
C6 C1 C2 C3 -0.4(4) . . . .
S1 C1 C2 C3 179.44(19) . . . .
C1 C2 C3 C4 1.0(4) . . . .
C2 C3 C4 C5 -1.3(4) . . . .
C2 C3 C4 C7 177.9(3) . . . .
C3 C4 C5 C6 1.0(4) . . . .
C7 C4 C5 C6 -178.2(3) . . . .
C4 C5 C6 C1 -0.4(4) . . . .
C2 C1 C6 C5 0.1(4) . . . .
S1 C1 C6 C5 -179.8(2) . . . .
N1 C8 C9 C14 -67.0(3) . . . .
N1 C8 C9 C10 116.6(3) . . . .
C14 C9 C10 C11 -1.3(4) . . . .
C8 C9 C10 C11 175.1(3) . . . .
C9 C10 C11 C12 0.7(5) . . . .
C10 C11 C12 C13 0.7(5) . . . .
C11 C12 C13 C14 -1.4(5) . . . .
C10 C9 C14 C13 0.6(4) . . . .
C8 C9 C14 C13 -175.8(2) . . . .
C12 C13 C14 C9 0.7(5) . . . .
O3 C15 C16 C17 3.0(4) . . . .
O4 C15 C16 C17 -176.3(2) . . . .
O3 C15 C16 C21 -177.4(3) . . . .
O4 C15 C16 C21 3.3(3) . . . .
C21 C16 C17 C18 0.2(4) . . . .
C15 C16 C17 C18 179.7(3) . . . .
C16 C17 C18 C19 -0.2(4) . . . .
C17 C18 C19 C20 0.3(5) . . . .
C18 C19 C20 C21 -0.5(4) . . . .
C19 C20 C21 C16 0.5(4) . . . .
C19 C20 C21 C22 -177.9(2) . . . .
C17 C16 C21 C20 -0.3(4) . . . .
C15 C16 C21 C20 -179.9(2) . . . .
C17 C16 C21 C22 178.1(2) . . . .
C15 C16 C21 C22 -1.4(3) . . . .
C20 C21 C22 C23 176.2(2) . . . .
C16 C21 C22 C23 -2.2(3) . . . .
C20 C21 C22 C24 -4.3(3) . . . .
C16 C21 C22 C24 177.3(2) . . . .
C21 C22 C23 O4 4.1(3) . . . .
C24 C22 C23 O4 -175.4(2) . . . .
C21 C22 C23 N1 -173.0(2) . . . .
C24 C22 C23 N1 7.5(3) . . . .
C23 C22 C24 C25 -90.9(3) . . . .
C21 C22 C24 C25 89.5(3) . . . .
C23 C22 C24 C29 90.2(3) . . . .
C21 C22 C24 C29 -89.4(3) . . . .
C29 C24 C25 C26 -3.1(4) . . . .
C22 C24 C25 C26 178.0(2) . . . .
C24 C25 C26 C27 0.2(4) . . . .
C25 C26 C27 C28 2.5(4) . . . .
C25 C26 C27 C30 -177.0(2) . . . .
C26 C27 C28 C29 -2.3(4) . . . .
C30 C27 C28 C29 177.3(2) . . . .
C27 C28 C29 C24 -0.7(4) . . . .
C25 C24 C29 C28 3.4(3) . . . .
C22 C24 C29 C28 -177.7(2) . . . .
C36 C31 C32 C33 -1.7(4) . . . .
S2 C31 C32 C33 175.3(2) . . . .
C31 C32 C33 C34 0.0(4) . . . .
C32 C33 C34 C35 1.9(4) . . . .
C32 C33 C34 C37 -176.3(3) . . . .
C33 C34 C35 C36 -2.2(4) . . . .
C37 C34 C35 C36 176.0(3) . . . .
C34 C35 C36 C31 0.5(4) . . . .
C32 C31 C36 C35 1.5(4) . . . .
S2 C31 C36 C35 -175.5(2) . . . .
N2 C38 C39 C44 -121.6(3) . . . .
N2 C38 C39 C40 61.0(3) . . . .
C44 C39 C40 C41 0.8(4) . . . .
C38 C39 C40 C41 178.2(2) . . . .
C39 C40 C41 C42 -0.8(4) . . . .
C40 C41 C42 C43 0.3(4) . . . .
C41 C42 C43 C44 0.3(5) . . . .
C42 C43 C44 C39 -0.4(5) . . . .
C40 C39 C44 C43 -0.1(4) . . . .
C38 C39 C44 C43 -177.6(3) . . . .
O7 C45 C46 C47 0.3(4) . . . .
O8 C45 C46 C47 -179.2(2) . . . .
O7 C45 C46 C51 179.6(3) . . . .
O8 C45 C46 C51 0.1(3) . . . .
C51 C46 C47 C48 1.1(4) . . . .
C45 C46 C47 C48 -179.6(3) . . . .
C46 C47 C48 C49 -0.1(4) . . . .
C47 C48 C49 C50 -0.3(4) . . . .
C48 C49 C50 C51 -0.4(4) . . . .
C49 C50 C51 C46 1.4(4) . . . .
C49 C50 C51 C52 -179.8(2) . . . .
C47 C46 C51 C50 -1.7(4) . . . .
C45 C46 C51 C50 179.0(2) . . . .
C47 C46 C51 C52 179.4(2) . . . .
C45 C46 C51 C52 0.2(3) . . . .
C50 C51 C52 C53 -178.0(2) . . . .
C46 C51 C52 C53 0.8(3) . . . .
C50 C51 C52 C54 2.3(3) . . . .
C46 C51 C52 C54 -178.9(2) . . . .
C51 C52 C53 O8 -2.0(3) . . . .
C54 C52 C53 O8 177.68(19) . . . .
C51 C52 C53 N2 173.4(2) . . . .
C54 C52 C53 N2 -6.9(4) . . . .
C53 C52 C54 C59 -86.3(3) . . . .
C51 C52 C54 C59 93.4(3) . . . .
C53 C52 C54 C55 95.2(3) . . . .
C51 C52 C54 C55 -85.1(3) . . . .
C59 C54 C55 C56 3.3(4) . . . .
C52 C54 C55 C56 -178.2(2) . . . .
C54 C55 C56 C57 -0.7(4) . . . .
C55 C56 C57 C58 -2.4(4) . . . .
C55 C56 C57 C60 177.1(3) . . . .
C56 C57 C58 C59 2.8(4) . . . .
C60 C57 C58 C59 -176.6(3) . . . .
C57 C58 C59 C54 -0.2(4) . . . .
C55 C54 C59 C58 -2.8(4) . . . .
C52 C54 C59 C58 178.6(2) . . . .
C22 C23 N1 C8 125.1(2) . . . .
O4 C23 N1 C8 -52.3(2) . . . .
C22 C23 N1 S1 -97.1(2) . . . .
O4 C23 N1 S1 85.45(19) . . . .
C9 C8 N1 C23 -57.2(3) . . . .
C9 C8 N1 S1 163.54(16) . . . .
C52 C53 N2 C38 -120.4(3) . . . .
O8 C53 N2 C38 55.5(3) . . . .
C52 C53 N2 S2 99.0(3) . . . .
O8 C53 N2 S2 -85.1(2) . . . .
C39 C38 N2 C53 66.1(3) . . . .
C39 C38 N2 S2 -151.70(18) . . . .
O3 C15 O4 C23 179.0(2) . . . .
C16 C15 O4 C23 -1.5(3) . . . .
C22 C23 O4 C15 -2.3(3) . . . .
N1 C23 O4 C15 175.2(2) . . . .
O7 C45 O8 C53 179.2(2) . . . .
C46 C45 O8 C53 -1.3(3) . . . .
C52 C53 O8 C45 2.4(3) . . . .
N2 C53 O8 C45 -173.7(2) . . . .
C23 N1 S1 O1 -98.98(17) . . . .
C8 N1 S1 O1 39.3(2) . . . .
C23 N1 S1 O2 31.65(18) . . . .
C8 N1 S1 O2 169.94(16) . . . .
C23 N1 S1 C1 147.25(16) . . . .
C8 N1 S1 C1 -74.47(18) . . . .
C2 C1 S1 O1 -9.8(2) . . . .
C6 C1 S1 O1 170.01(19) . . . .
C2 C1 S1 O2 -141.13(19) . . . .
C6 C1 S1 O2 38.7(2) . . . .
C2 C1 S1 N1 106.3(2) . . . .
C6 C1 S1 N1 -73.9(2) . . . .
C53 N2 S2 O5 99.1(2) . . . .
C38 N2 S2 O5 -41.4(2) . . . .
C53 N2 S2 O6 -31.3(2) . . . .
C38 N2 S2 O6 -171.78(18) . . . .
C53 N2 S2 C31 -147.26(18) . . . .
C38 N2 S2 C31 72.3(2) . . . .
C36 C31 S2 O5 -168.5(2) . . . .
C32 C31 S2 O5 14.6(2) . . . .
C36 C31 S2 O6 -36.4(2) . . . .
C32 C31 S2 O6 146.7(2) . . . .
C36 C31 S2 N2 75.7(2) . . . .
C32 C31 S2 N2 -101.3(2) . . . .
