#------------------------------------------------------------------------------
#$Date: 2021-05-14 04:08:02 +0300 (Fri, 14 May 2021) $
#$Revision: 265202 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/25/1562554.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_1562554
loop_
_publ_author_name
'Grundy, Matthew'
'Yuan, Kang'
'Nichol, Gary Stephen'
'Ingleson, Michael James'
_publ_section_title
;
 Zinc catalysed electrophilic C-H borylation of heteroarenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01883C
_journal_year                    2021
_chemical_formula_moiety         'C2 F6 N O4 S2, C33 H48 B N2 O2'
_chemical_formula_sum            'C35 H48 B F6 N3 O6 S2'
_chemical_formula_weight         795.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-16
_audit_creation_method
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-03-30 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.607(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.260(5)
_cell_length_b                   12.118(3)
_cell_length_c                   19.857(7)
_cell_measurement_reflns_used    3278
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      19.63
_cell_measurement_theta_min      2.34
_cell_volume                     4069(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1146
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            37868
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        19.796
_diffrn_reflns_theta_max         19.796
_diffrn_reflns_theta_min         2.337
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.7444
_exptl_absorpt_correction_T_min  0.5586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0961 before and 0.0772 after correction.
The Ratio of minimum to maximum transmission is 0.7504.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       plate
_exptl_crystal_F_000             1672
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.0076(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         3681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0593
_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)+(0.0709P)²+5.4062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1605
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2694
_reflns_number_total             3681
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc01883c2.cif
_cod_data_source_block           mi19009
_cod_database_code               1562554
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.925
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C),
 C33(H33A,H33B,H33C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800'
_olex2_submission_original_sample_id MG149
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S1 S 0.66914(9) 0.71769(12) 0.13579(8) 0.0460(5) Uani 1 1 d . . . . .
S2 S 0.82728(9) 0.66372(14) 0.18205(8) 0.0499(5) Uani 1 1 d . . . . .
F1 F 0.5854(2) 0.5489(4) 0.0600(3) 0.0916(13) Uani 1 1 d . . . . .
F2 F 0.5335(3) 0.7074(4) 0.0160(2) 0.1162(18) Uani 1 1 d . . . . .
F3 F 0.6277(3) 0.6473(4) -0.0024(2) 0.0944(14) Uani 1 1 d . . . . .
F4 F 0.8364(3) 0.7915(3) 0.2913(2) 0.0900(13) Uani 1 1 d . . . . .
F5 F 0.9488(3) 0.7281(4) 0.3080(2) 0.0977(14) Uani 1 1 d . . . . .
F6 F 0.8692(2) 0.6250(3) 0.32580(19) 0.0682(11) Uani 1 1 d . . . . .
O3 O 0.6799(3) 0.8245(3) 0.1129(3) 0.0702(13) Uani 1 1 d . . . . .
O4 O 0.6338(2) 0.7084(3) 0.1839(2) 0.0596(12) Uani 1 1 d . . . . .
O5 O 0.8367(3) 0.7565(4) 0.1436(3) 0.0787(15) Uani 1 1 d . . . . .
O6 O 0.8662(2) 0.5627(3) 0.1831(2) 0.0586(12) Uani 1 1 d . . . . .
N3 N 0.7406(2) 0.6353(3) 0.1638(2) 0.0396(12) Uani 1 1 d . . . . .
C34 C 0.6000(4) 0.6510(7) 0.0470(4) 0.070(2) Uani 1 1 d . . . . .
C35 C 0.8731(4) 0.7048(6) 0.2822(4) 0.0621(18) Uani 1 1 d . . . . .
O1 O 0.7397(2) 0.2338(3) 0.4529(2) 0.0478(11) Uani 1 1 d . . . . .
O2 O 0.8221(2) 0.1448(3) 0.4192(2) 0.0478(11) Uani 1 1 d . . . . .
N1 N 0.6943(2) 0.3927(3) 0.3159(2) 0.0304(11) Uani 1 1 d . . . . .
N2 N 0.7752(2) 0.3108(3) 0.2873(2) 0.0322(11) Uani 1 1 d . . . . .
C1 C 0.7447(3) 0.3068(4) 0.3356(3) 0.0310(13) Uani 1 1 d . . . . .
C2 C 0.6945(3) 0.4509(4) 0.2575(3) 0.0338(13) Uani 1 1 d . . . . .
H2 H 0.664458 0.515123 0.233764 0.041 Uiso 1 1 calc R U . . .
C3 C 0.7458(3) 0.3993(4) 0.2400(3) 0.0364(14) Uani 1 1 d . . . . .
H3 H 0.759060 0.421038 0.201542 0.044 Uiso 1 1 calc R U . . .
C4 C 0.6445(3) 0.4202(4) 0.3504(3) 0.0317(13) Uani 1 1 d . . . . .
C5 C 0.5742(3) 0.3624(4) 0.3258(3) 0.0350(14) Uani 1 1 d . . . . .
C6 C 0.5279(3) 0.3919(5) 0.3587(3) 0.0407(14) Uani 1 1 d . . . . .
H6 H 0.479553 0.354043 0.344261 0.049 Uiso 1 1 calc R U . . .
C7 C 0.5505(3) 0.4747(5) 0.4118(3) 0.0401(15) Uani 1 1 d . . . . .
H7 H 0.517285 0.493719 0.433177 0.048 Uiso 1 1 calc R U . . .
C8 C 0.6198(3) 0.5310(4) 0.4348(3) 0.0381(14) Uani 1 1 d . . . . .
H8 H 0.634020 0.588380 0.471669 0.046 Uiso 1 1 calc R U . . .
C9 C 0.6699(3) 0.5046(4) 0.4043(3) 0.0350(14) Uani 1 1 d . . . . .
C10 C 0.5465(3) 0.2725(4) 0.2652(3) 0.0429(15) Uani 1 1 d . . . . .
H10 H 0.589511 0.259835 0.251517 0.051 Uiso 1 1 calc R U . . .
C11 C 0.5310(4) 0.1637(5) 0.2935(4) 0.0576(17) Uani 1 1 d . . . . .
H11A H 0.579164 0.139602 0.339039 0.086 Uiso 1 1 calc R U . . .
H11B H 0.515484 0.107855 0.253078 0.086 Uiso 1 1 calc R U . . .
H11C H 0.488356 0.173238 0.306583 0.086 Uiso 1 1 calc R U . . .
C12 C 0.4729(4) 0.3104(6) 0.1924(4) 0.084(2) Uani 1 1 d . . . . .
H12A H 0.430184 0.326143 0.204533 0.126 Uiso 1 1 calc R U . . .
H12B H 0.456070 0.251954 0.153629 0.126 Uiso 1 1 calc R U . . .
H12C H 0.485355 0.377234 0.172571 0.126 Uiso 1 1 calc R U . . .
C13 C 0.7488(3) 0.5621(4) 0.4315(3) 0.0373(14) Uani 1 1 d . . . . .
H13 H 0.776372 0.528206 0.404878 0.045 Uiso 1 1 calc R U . . .
C14 C 0.8001(4) 0.5456(6) 0.5178(3) 0.072(2) Uani 1 1 d . . . . .
H14A H 0.775162 0.581705 0.544926 0.109 Uiso 1 1 calc R U . . .
H14B H 0.852462 0.577891 0.534382 0.109 Uiso 1 1 calc R U . . .
H14C H 0.805694 0.466462 0.529551 0.109 Uiso 1 1 calc R U . . .
C15 C 0.7387(4) 0.6836(5) 0.4136(4) 0.0666(19) Uani 1 1 d . . . . .
H15A H 0.706523 0.694086 0.358124 0.100 Uiso 1 1 calc R U . . .
H15B H 0.790689 0.717640 0.431151 0.100 Uiso 1 1 calc R U . . .
H15C H 0.712296 0.718150 0.439897 0.100 Uiso 1 1 calc R U . . .
C16 C 0.8253(3) 0.2265(4) 0.2794(3) 0.0345(14) Uani 1 1 d . . . . .
C17 C 0.9065(4) 0.2397(5) 0.3185(3) 0.0408(15) Uani 1 1 d . . . . .
C18 C 0.9498(4) 0.1567(6) 0.3072(4) 0.0527(17) Uani 1 1 d . . . . .
H18 H 1.005870 0.161819 0.332200 0.063 Uiso 1 1 calc R U . . .
C19 C 0.9136(4) 0.0677(5) 0.2608(4) 0.0492(16) Uani 1 1 d . . . . .
H19 H 0.944725 0.011776 0.254689 0.059 Uiso 1 1 calc R U . . .
C20 C 0.8337(4) 0.0591(5) 0.2237(3) 0.0489(16) Uani 1 1 d . . . . .
H20 H 0.809969 -0.003511 0.192186 0.059 Uiso 1 1 calc R U . . .
C21 C 0.7851(3) 0.1390(4) 0.2301(3) 0.0386(15) Uani 1 1 d . . . . .
C22 C 0.9466(3) 0.3367(5) 0.3710(3) 0.0476(16) Uani 1 1 d . . . . .
H22 H 0.904750 0.383119 0.373142 0.057 Uiso 1 1 calc R U . . .
C23 C 1.0036(4) 0.2989(6) 0.4523(4) 0.075(2) Uani 1 1 d . . . . .
H23A H 1.047545 0.258278 0.452200 0.113 Uiso 1 1 calc R U . . .
H23B H 0.975676 0.250718 0.471057 0.113 Uiso 1 1 calc R U . . .
H23C H 1.024235 0.363379 0.485957 0.113 Uiso 1 1 calc R U . . .
C24 C 0.9893(4) 0.4074(5) 0.3385(4) 0.0594(18) Uani 1 1 d . . . . .
H24A H 1.011008 0.473291 0.370459 0.089 Uiso 1 1 calc R U . . .
H24B H 0.951813 0.429675 0.285995 0.089 Uiso 1 1 calc R U . . .
H24C H 1.032312 0.364652 0.338270 0.089 Uiso 1 1 calc R U . . .
C25 C 0.6964(4) 0.1278(5) 0.1889(3) 0.0484(16) Uani 1 1 d . . . . .
H25 H 0.673909 0.200257 0.193122 0.058 Uiso 1 1 calc R U . . .
C26 C 0.6704(4) 0.0413(5) 0.2279(3) 0.0634(19) Uani 1 1 d . . . . .
H26A H 0.612509 0.036935 0.201621 0.095 Uiso 1 1 calc R U . . .
H26B H 0.689598 0.061880 0.281629 0.095 Uiso 1 1 calc R U . . .
H26C H 0.692300 -0.030707 0.225459 0.095 Uiso 1 1 calc R U . . .
C27 C 0.6629(4) 0.1025(5) 0.1042(3) 0.0533(17) Uani 1 1 d . . . . .
H27A H 0.680868 0.029379 0.098067 0.080 Uiso 1 1 calc R U . . .
H27B H 0.681114 0.158221 0.080483 0.080 Uiso 1 1 calc R U . . .
H27C H 0.604977 0.103463 0.079404 0.080 Uiso 1 1 calc R U . . .
C28 C 0.7850(4) 0.1559(5) 0.5163(3) 0.0486(16) Uani 1 1 d . . . . .
C29 C 0.8236(4) 0.0782(5) 0.4821(3) 0.0487(17) Uani 1 1 d . . . . .
C30 C 0.8440(4) 0.2230(5) 0.5829(3) 0.072(2) Uani 1 1 d . . . . .
H30A H 0.883297 0.254049 0.570233 0.109 Uiso 1 1 calc R U . . .
H30B H 0.870490 0.175639 0.628212 0.109 Uiso 1 1 calc R U . . .
H30C H 0.816550 0.283011 0.593569 0.109 Uiso 1 1 calc R U . . .
C31 C 0.7263(4) 0.1036(6) 0.5360(4) 0.071(2) Uani 1 1 d . . . . .
H31A H 0.704468 0.160013 0.555937 0.107 Uiso 1 1 calc R U . . .
H31B H 0.752695 0.046512 0.574994 0.107 Uiso 1 1 calc R U . . .
H31C H 0.683415 0.070211 0.489851 0.107 Uiso 1 1 calc R U . . .
C32 C 0.9070(4) 0.0469(6) 0.5349(4) 0.082(2) Uani 1 1 d . . . . .
H32A H 0.909699 0.005969 0.578597 0.123 Uiso 1 1 calc R U . . .
H32B H 0.939474 0.113735 0.553343 0.123 Uiso 1 1 calc R U . . .
H32C H 0.926954 0.000507 0.507439 0.123 Uiso 1 1 calc R U . . .
C33 C 0.7740(5) -0.0238(5) 0.4441(4) 0.084(2) Uani 1 1 d . . . . .
H33A H 0.792292 -0.057716 0.410547 0.126 Uiso 1 1 calc R U . . .
H33B H 0.718379 -0.002558 0.413648 0.126 Uiso 1 1 calc R U . . .
H33C H 0.779528 -0.076855 0.483618 0.126 Uiso 1 1 calc R U . . .
B1 B 0.7693(4) 0.2240(5) 0.4040(3) 0.0319(16) 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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 -1.00 0.0860
0.00 0.00 -1.00 0.0490
0.00 0.00 1.00 0.0330
-1.00 0.00 0.00 0.0170
1.00 0.00 0.00 0.0070
0.00 1.00 -1.00 0.1420
-1.00 0.00 1.00 0.0280
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
_geom_angle_publ_flag
O3 S1 N3 117.1(3) . . ?
O3 S1 C34 104.3(3) . . ?
O4 S1 O3 118.6(3) . . ?
O4 S1 N3 109.4(2) . . ?
O4 S1 C34 104.7(3) . . ?
N3 S1 C34 99.9(3) . . ?
O5 S2 O6 119.1(3) . . ?
O5 S2 N3 116.5(3) . . ?
O5 S2 C35 104.5(3) . . ?
O6 S2 N3 107.9(2) . . ?
O6 S2 C35 104.0(3) . . ?
N3 S2 C35 102.6(3) . . ?
S2 N3 S1 126.7(3) . . ?
F1 C34 S1 110.8(5) . . ?
F1 C34 F3 108.2(6) . . ?
F2 C34 S1 108.7(5) . . ?
F2 C34 F1 109.1(7) . . ?
F2 C34 F3 108.5(6) . . ?
F3 C34 S1 111.5(5) . . ?
F4 C35 S2 110.8(5) . . ?
F5 C35 S2 110.5(5) . . ?
F5 C35 F4 109.7(6) . . ?
F6 C35 S2 111.5(5) . . ?
F6 C35 F4 106.8(6) . . ?
F6 C35 F5 107.4(6) . . ?
B1 O1 C28 106.0(4) . . ?
B1 O2 C29 106.8(4) . . ?
C1 N1 C2 110.6(4) . . ?
C1 N1 C4 125.8(4) . . ?
C2 N1 C4 123.6(4) . . ?
C1 N2 C3 110.0(4) . . ?
C1 N2 C16 125.9(4) . . ?
C3 N2 C16 123.7(4) . . ?
N1 C1 B1 128.5(5) . . ?
N2 C1 N1 105.4(4) . . ?
N2 C1 B1 125.9(5) . . ?
N1 C2 H2 126.8 . . ?
C3 C2 N1 106.4(4) . . ?
C3 C2 H2 126.8 . . ?
N2 C3 H3 126.2 . . ?
C2 C3 N2 107.5(4) . . ?
C2 C3 H3 126.2 . . ?
C5 C4 N1 118.0(4) . . ?
C9 C4 N1 117.5(5) . . ?
C9 C4 C5 124.5(5) . . ?
C4 C5 C10 123.6(5) . . ?
C6 C5 C4 116.4(5) . . ?
C6 C5 C10 120.0(5) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.0(5) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.6(5) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.4(5) . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 116.1(5) . . ?
C4 C9 C13 122.5(5) . . ?
C8 C9 C13 121.4(5) . . ?
C5 C10 H10 107.6 . . ?
C5 C10 C12 110.4(5) . . ?
C11 C10 C5 112.7(5) . . ?
C11 C10 H10 107.6 . . ?
C11 C10 C12 110.7(5) . . ?
C12 C10 H10 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13 108.5 . . ?
C9 C13 C14 109.9(4) . . ?
C14 C13 H13 108.5 . . ?
C15 C13 C9 111.8(5) . . ?
C15 C13 H13 108.5 . . ?
C15 C13 C14 109.5(5) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 N2 119.0(5) . . ?
C17 C16 C21 125.4(5) . . ?
C21 C16 N2 115.5(5) . . ?
C16 C17 C18 115.5(5) . . ?
C16 C17 C22 122.9(5) . . ?
C18 C17 C22 121.7(6) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.7(6) . . ?
C19 C18 H18 119.2 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.3(6) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 118.8 . . ?
C19 C20 C21 122.3(6) . . ?
C21 C20 H20 118.8 . . ?
C16 C21 C25 123.5(5) . . ?
C20 C21 C16 114.8(5) . . ?
C20 C21 C25 121.7(5) . . ?
C17 C22 H22 108.1 . . ?
C17 C22 C23 111.5(5) . . ?
C17 C22 C24 110.1(5) . . ?
C23 C22 H22 108.1 . . ?
C23 C22 C24 110.8(5) . . ?
C24 C22 H22 108.1 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 H25 107.5 . . ?
C21 C25 C26 110.5(5) . . ?
C21 C25 C27 113.0(5) . . ?
C26 C25 H25 107.5 . . ?
C27 C25 H25 107.5 . . ?
C27 C25 C26 110.8(5) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O1 C28 C29 103.2(4) . . ?
O1 C28 C30 107.1(5) . . ?
O1 C28 C31 106.2(5) . . ?
C30 C28 C29 113.3(5) . . ?
C31 C28 C29 116.0(5) . . ?
C31 C28 C30 110.2(5) . . ?
O2 C29 C28 102.7(4) . . ?
O2 C29 C32 108.2(5) . . ?
O2 C29 C33 105.7(5) . . ?
C32 C29 C28 115.6(5) . . ?
C32 C29 C33 110.6(6) . . ?
C33 C29 C28 113.2(5) . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C29 C33 H33A 109.5 . . ?
C29 C33 H33B 109.5 . . ?
C29 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O1 B1 C1 120.7(5) . . ?
O2 B1 O1 116.4(5) . . ?
O2 B1 C1 122.8(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.420(4) . ?
S1 O4 1.419(4) . ?
S1 N3 1.571(4) . ?
S1 C34 1.813(7) . ?
S2 O5 1.419(4) . ?
S2 O6 1.430(4) . ?
S2 N3 1.568(4) . ?
S2 C35 1.817(7) . ?
F1 C34 1.321(8) . ?
F2 C34 1.317(7) . ?
F3 C34 1.324(8) . ?
F4 C35 1.326(7) . ?
F5 C35 1.324(7) . ?
F6 C35 1.324(7) . ?
O1 C28 1.478(6) . ?
O1 B1 1.346(7) . ?
O2 C29 1.477(6) . ?
O2 B1 1.324(7) . ?
N1 C1 1.347(6) . ?
N1 C2 1.359(6) . ?
N1 C4 1.459(6) . ?
N2 C1 1.346(6) . ?
N2 C3 1.358(6) . ?
N2 C16 1.465(6) . ?
C1 B1 1.569(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.349(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(7) . ?
C4 C9 1.388(7) . ?
C5 C6 1.381(7) . ?
C5 C10 1.519(7) . ?
C6 H6 0.9500 . ?
C6 C7 1.367(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.368(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.400(7) . ?
C9 C13 1.517(7) . ?
C10 H10 1.0000 . ?
C10 C11 1.518(7) . ?
C10 C12 1.531(8) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 1.0000 . ?
C13 C14 1.527(8) . ?
C13 C15 1.505(7) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.383(8) . ?
C16 C21 1.399(7) . ?
C17 C18 1.391(8) . ?
C17 C22 1.515(8) . ?
C18 H18 0.9500 . ?
C18 C19 1.372(8) . ?
C19 H19 0.9500 . ?
C19 C20 1.355(8) . ?
C20 H20 0.9500 . ?
C20 C21 1.394(8) . ?
C21 C25 1.506(8) . ?
C22 H22 1.0000 . ?
C22 C23 1.525(8) . ?
C22 C24 1.527(8) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25 1.0000 . ?
C25 C26 1.524(8) . ?
C25 C27 1.515(8) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.543(8) . ?
C28 C30 1.504(8) . ?
C28 C31 1.502(8) . ?
C29 C32 1.487(9) . ?
C29 C33 1.523(9) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
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
_geom_torsion_publ_flag
O3 S1 N3 S2 10.8(4) . . . . ?
O3 S1 C34 F1 179.1(5) . . . . ?
O3 S1 C34 F2 -61.0(6) . . . . ?
O3 S1 C34 F3 58.6(6) . . . . ?
O4 S1 N3 S2 -127.9(3) . . . . ?
O4 S1 C34 F1 -55.6(5) . . . . ?
O4 S1 C34 F2 64.3(6) . . . . ?
O4 S1 C34 F3 -176.1(5) . . . . ?
O5 S2 N3 S1 -26.0(5) . . . . ?
O5 S2 C35 F4 61.6(6) . . . . ?
O5 S2 C35 F5 -60.3(6) . . . . ?
O5 S2 C35 F6 -179.6(5) . . . . ?
O6 S2 N3 S1 -163.0(3) . . . . ?
O6 S2 C35 F4 -172.8(5) . . . . ?
O6 S2 C35 F5 65.3(5) . . . . ?
O6 S2 C35 F6 -54.0(5) . . . . ?
N3 S1 C34 F1 57.6(5) . . . . ?
N3 S1 C34 F2 177.5(5) . . . . ?
N3 S1 C34 F3 -62.9(5) . . . . ?
N3 S2 C35 F4 -60.5(5) . . . . ?
N3 S2 C35 F5 177.7(5) . . . . ?
N3 S2 C35 F6 58.3(5) . . . . ?
C34 S1 N3 S2 122.6(4) . . . . ?
C35 S2 N3 S1 87.6(4) . . . . ?
O1 C28 C29 O2 21.4(6) . . . . ?
O1 C28 C29 C32 139.0(5) . . . . ?
O1 C28 C29 C33 -92.0(5) . . . . ?
N1 C1 B1 O1 -0.5(8) . . . . ?
N1 C1 B1 O2 -177.3(5) . . . . ?
N1 C2 C3 N2 0.5(6) . . . . ?
N1 C4 C5 C6 -178.9(4) . . . . ?
N1 C4 C5 C10 -0.1(7) . . . . ?
N1 C4 C9 C8 178.4(4) . . . . ?
N1 C4 C9 C13 -4.2(7) . . . . ?
N2 C1 B1 O1 174.1(5) . . . . ?
N2 C1 B1 O2 -2.7(8) . . . . ?
N2 C16 C17 C18 -179.2(4) . . . . ?
N2 C16 C17 C22 1.5(7) . . . . ?
N2 C16 C21 C20 -179.5(4) . . . . ?
N2 C16 C21 C25 -1.9(7) . . . . ?
C1 N1 C2 C3 0.5(6) . . . . ?
C1 N1 C4 C5 -80.6(6) . . . . ?
C1 N1 C4 C9 100.9(6) . . . . ?
C1 N2 C3 C2 -1.4(6) . . . . ?
C1 N2 C16 C17 -96.7(6) . . . . ?
C1 N2 C16 C21 84.9(6) . . . . ?
C2 N1 C1 N2 -1.3(5) . . . . ?
C2 N1 C1 B1 174.1(5) . . . . ?
C2 N1 C4 C5 98.1(6) . . . . ?
C2 N1 C4 C9 -80.4(6) . . . . ?
C3 N2 C1 N1 1.7(5) . . . . ?
C3 N2 C1 B1 -174.0(5) . . . . ?
C3 N2 C16 C17 90.9(6) . . . . ?
C3 N2 C16 C21 -87.5(6) . . . . ?
C4 N1 C1 N2 177.5(4) . . . . ?
C4 N1 C1 B1 -7.0(8) . . . . ?
C4 N1 C2 C3 -178.4(4) . . . . ?
C4 C5 C6 C7 0.8(7) . . . . ?
C4 C5 C10 C11 123.6(5) . . . . ?
C4 C5 C10 C12 -112.1(6) . . . . ?
C4 C9 C13 C14 -119.1(6) . . . . ?
C4 C9 C13 C15 119.1(6) . . . . ?
C5 C4 C9 C8 0.0(7) . . . . ?
C5 C4 C9 C13 177.5(5) . . . . ?
C5 C6 C7 C8 -0.5(8) . . . . ?
C6 C5 C10 C11 -57.5(7) . . . . ?
C6 C5 C10 C12 66.8(7) . . . . ?
C6 C7 C8 C9 -0.1(8) . . . . ?
C7 C8 C9 C4 0.4(7) . . . . ?
C7 C8 C9 C13 -177.1(5) . . . . ?
C8 C9 C13 C14 58.2(7) . . . . ?
C8 C9 C13 C15 -63.6(6) . . . . ?
C9 C4 C5 C6 -0.6(7) . . . . ?
C9 C4 C5 C10 178.3(5) . . . . ?
C10 C5 C6 C7 -178.1(5) . . . . ?
C16 N2 C1 N1 -171.6(4) . . . . ?
C16 N2 C1 B1 12.7(8) . . . . ?
C16 N2 C3 C2 172.1(5) . . . . ?
C16 C17 C18 C19 -0.6(8) . . . . ?
C16 C17 C22 C23 121.5(6) . . . . ?
C16 C17 C22 C24 -115.1(6) . . . . ?
C16 C21 C25 C26 -103.3(6) . . . . ?
C16 C21 C25 C27 132.0(5) . . . . ?
C17 C16 C21 C20 2.1(7) . . . . ?
C17 C16 C21 C25 179.8(5) . . . . ?
C17 C18 C19 C20 0.8(8) . . . . ?
C18 C17 C22 C23 -57.7(7) . . . . ?
C18 C17 C22 C24 65.7(7) . . . . ?
C18 C19 C20 C21 0.5(8) . . . . ?
C19 C20 C21 C16 -1.8(8) . . . . ?
C19 C20 C21 C25 -179.5(5) . . . . ?
C20 C21 C25 C26 74.2(6) . . . . ?
C20 C21 C25 C27 -50.5(7) . . . . ?
C21 C16 C17 C18 -1.0(8) . . . . ?
C21 C16 C17 C22 179.8(5) . . . . ?
C22 C17 C18 C19 178.7(5) . . . . ?
C28 O1 B1 O2 6.4(6) . . . . ?
C28 O1 B1 C1 -170.7(5) . . . . ?
C29 O2 B1 O1 8.4(6) . . . . ?
C29 O2 B1 C1 -174.6(5) . . . . ?
C30 C28 C29 O2 -94.0(5) . . . . ?
C30 C28 C29 C32 23.6(7) . . . . ?
C30 C28 C29 C33 152.6(5) . . . . ?
C31 C28 C29 O2 137.1(5) . . . . ?
C31 C28 C29 C32 -105.3(7) . . . . ?
C31 C28 C29 C33 23.7(7) . . . . ?
B1 O1 C28 C29 -17.4(6) . . . . ?
B1 O1 C28 C30 102.5(5) . . . . ?
B1 O1 C28 C31 -139.8(5) . . . . ?
B1 O2 C29 C28 -18.5(6) . . . . ?
B1 O2 C29 C32 -141.2(5) . . . . ?
B1 O2 C29 C33 100.4(5) . . . . ?
