# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_goa42
_database_code_depnum_ccdc_archive 'CCDC 1981082'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2020-01-31 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H27 Br N8 O5 S'
_chemical_formula_sum            'C27 H27 Br N8 O5 S'
_chemical_formula_weight         655.53

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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'

_cell_length_a                   9.7202(14)
_cell_length_b                   11.6843(16)
_cell_length_c                   24.726(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.705(3)
_cell_angle_gamma                90
_cell_volume                     2802.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    399
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.340
_exptl_absorpt_coefficient_mu    1.596
_shelx_estimated_absorpt_T_min   0.561
_shelx_estimated_absorpt_T_max   0.613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3175
_exptl_absorpt_correction_T_max  0.4331
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48478
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.928
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8165
_reflns_number_gt                6265
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0643P)²+3.6022P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8165
_refine_ls_number_parameters     387
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br1 Br -0.14081(3) 1.01589(3) 0.05969(2) 0.03966(10) Uani 1 1 d . . . . .
S1 S 0.22442(6) 0.53014(5) 0.16820(2) 0.01910(12) Uani 1 1 d . . . . .
O1 O -0.2358(2) 0.29400(18) 0.19646(8) 0.0325(4) Uani 1 1 d . . . . .
O2 O -0.01781(17) 0.59782(15) 0.04399(7) 0.0217(3) Uani 1 1 d . . . . .
O3 O 0.49510(17) 0.65271(15) 0.13474(7) 0.0237(4) Uani 1 1 d . . . . .
O4 O 0.4522(3) -0.01158(18) 0.08480(11) 0.0440(6) Uani 1 1 d . . . . .
O5 O 0.5627(2) 0.06261(18) 0.15384(9) 0.0368(5) Uani 1 1 d . . . . .
N1 N -0.2409(2) 0.4838(2) 0.21987(10) 0.0297(5) Uani 1 1 d . . . . .
N2 N -0.1882(2) 0.4383(2) 0.13703(9) 0.0249(4) Uani 1 1 d . . . . .
N3 N -0.1066(2) 0.6596(2) 0.22505(10) 0.0273(5) Uani 1 1 d . . . . .
H3N H -0.127(3) 0.674(3) 0.2556(14) 0.032(9) Uiso 1 1 d . . . . .
N4 N 0.0266(2) 0.61203(19) 0.22868(9) 0.0244(4) Uani 1 1 d . . . . .
N5 N -0.0237(2) 0.58986(18) 0.13567(8) 0.0191(4) Uani 1 1 d . . . . .
N6 N 0.3020(2) 0.69151(17) 0.03323(8) 0.0198(4) Uani 1 1 d . . . . .
N7 N 0.3663(2) 0.79947(18) 0.16518(8) 0.0217(4) Uani 1 1 d . . . . .
N8 N 0.4822(2) 0.06893(19) 0.11434(9) 0.0270(5) Uani 1 1 d . . . . .
C1 C -0.2228(2) 0.3955(2) 0.18624(11) 0.0260(5) Uani 1 1 d . . . . .
C2 C -0.2128(3) 0.5937(2) 0.19593(10) 0.0257(5) Uani 1 1 d . . . . .
H2A H -0.299703 0.639602 0.192168 0.031 Uiso 1 1 calc R U . . .
C3 C -0.1688(2) 0.5603(2) 0.13919(10) 0.0228(5) Uani 1 1 d . . . . .
H3A H -0.227685 0.599394 0.110110 0.027 Uiso 1 1 calc R U . . .
C4 C 0.0624(2) 0.5816(2) 0.18272(9) 0.0190(4) Uani 1 1 d . . . . .
C5 C 0.0405(2) 0.59026(19) 0.08824(9) 0.0177(4) Uani 1 1 d . . . . .
C6 C 0.1980(2) 0.58101(19) 0.09827(9) 0.0168(4) Uani 1 1 d . . . . .
C7 C 0.2543(2) 0.50207(19) 0.05362(9) 0.0188(4) Uani 1 1 d . . . . .
H7A H 0.175896 0.486496 0.026432 0.023 Uiso 1 1 calc R U . . .
C8 C 0.3564(3) 0.5773(2) 0.02609(10) 0.0210(5) Uani 1 1 d . . . . .
H8A H 0.450283 0.569717 0.043735 0.025 Uiso 1 1 calc R U . . .
H8B H 0.358927 0.557872 -0.012809 0.025 Uiso 1 1 calc R U . . .
C9 C 0.2685(2) 0.7001(2) 0.08907(9) 0.0174(4) Uani 1 1 d . . . . .
C10 C 0.3929(2) 0.7125(2) 0.13152(10) 0.0197(4) Uani 1 1 d . . . . .
C11 C 0.2447(3) 0.8562(2) 0.14783(9) 0.0207(4) Uani 1 1 d . . . . .
C12 C 0.1915(3) 0.9552(2) 0.16866(10) 0.0262(5) Uani 1 1 d . . . . .
H12A H 0.233256 0.990412 0.200232 0.031 Uiso 1 1 calc R U . . .
C13 C 0.0746(3) 1.0012(2) 0.14169(11) 0.0263(5) Uani 1 1 d . . . . .
H13A H 0.034645 1.069015 0.154970 0.032 Uiso 1 1 calc R U . . .
C14 C 0.0164(3) 0.9492(2) 0.09580(10) 0.0244(5) Uani 1 1 d . . . . .
C15 C 0.0703(2) 0.8498(2) 0.07474(9) 0.0207(4) Uani 1 1 d . . . . .
H15A H 0.029648 0.815234 0.042801 0.025 Uiso 1 1 calc R U . . .
C16 C 0.1847(2) 0.8035(2) 0.10192(9) 0.0186(4) Uani 1 1 d . . . . .
C17 C 0.3119(2) 0.3883(2) 0.07201(10) 0.0198(4) Uani 1 1 d . . . . .
C18 C 0.2501(3) 0.2888(2) 0.05184(10) 0.0242(5) Uani 1 1 d . . . . .
H18A H 0.169478 0.293783 0.028076 0.029 Uiso 1 1 calc R U . . .
C19 C 0.3036(3) 0.1830(2) 0.06571(11) 0.0259(5) Uani 1 1 d . . . . .
H19A H 0.262735 0.114926 0.051153 0.031 Uiso 1 1 calc R U . . .
C20 C 0.4183(3) 0.1790(2) 0.10131(10) 0.0225(5) Uani 1 1 d . . . . .
C21 C 0.4809(3) 0.2751(2) 0.12301(10) 0.0229(5) Uani 1 1 d . . . . .
H21A H 0.558937 0.269263 0.148023 0.027 Uiso 1 1 calc R U . . .
C22 C 0.4280(3) 0.3804(2) 0.10775(10) 0.0229(5) Uani 1 1 d . . . . .
H22A H 0.471190 0.448120 0.121714 0.028 Uiso 1 1 calc R U . . .
C23 C -0.3212(3) 0.4746(3) 0.26693(13) 0.0402(7) Uani 1 1 d . . . . .
H23A H -0.323736 0.394515 0.278609 0.060 Uiso 1 1 calc R U . . .
H23B H -0.415361 0.501413 0.257698 0.060 Uiso 1 1 calc R U . . .
H23C H -0.279036 0.521589 0.296348 0.060 Uiso 1 1 calc R U . . .
C24 C -0.1278(3) 0.3651(2) 0.09795(11) 0.0282(5) Uani 1 1 d . . . . .
H24A H -0.161780 0.286750 0.101886 0.042 Uiso 1 1 calc R U . . .
H24B H -0.027244 0.365993 0.104147 0.042 Uiso 1 1 calc R U . . .
H24C H -0.153548 0.392817 0.061273 0.042 Uiso 1 1 calc R U . . .
C25 C 0.3884(3) 0.7815(2) 0.01373(11) 0.0269(5) Uani 1 1 d . . . . .
H25A H 0.345515 0.855994 0.019656 0.040 Uiso 1 1 calc R U . . .
H25B H 0.399146 0.770773 -0.025076 0.040 Uiso 1 1 calc R U . . .
H25C H 0.479167 0.778754 0.033432 0.040 Uiso 1 1 calc R U . . .
C26 C 0.4501(3) 0.8260(2) 0.21464(10) 0.0258(5) Uani 1 1 d . . . . .
H26A H 0.450936 0.909756 0.220640 0.031 Uiso 1 1 calc R U . . .
H26B H 0.546187 0.800755 0.210722 0.031 Uiso 1 1 calc R U . . .
C27 C 0.3938(3) 0.7670(3) 0.26264(11) 0.0356(6) Uani 1 1 d . . . . .
H27A H 0.448987 0.788385 0.295671 0.053 Uiso 1 1 calc R U . . .
H27B H 0.397954 0.683932 0.257605 0.053 Uiso 1 1 calc R U . . .
H27C H 0.297870 0.790386 0.265875 0.053 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Br1 C14 1.887(3) . ?
S1 C4 1.745(2) . ?
S1 C6 1.831(2) . ?
O1 C1 1.221(3) . ?
O2 C5 1.203(3) . ?
O3 C10 1.213(3) . ?
O4 N8 1.215(3) . ?
O5 N8 1.213(3) . ?
N1 C1 1.344(4) . ?
N1 C23 1.447(3) . ?
N1 C2 1.447(4) . ?
N2 C1 1.377(3) . ?
N2 C3 1.438(3) . ?
N2 C24 1.443(3) . ?
N3 N4 1.407(3) . ?
N3 C2 1.442(3) . ?
N3 H3N 0.81(3) . ?
N4 C4 1.261(3) . ?
N5 C5 1.364(3) . ?
N5 C4 1.392(3) . ?
N5 C3 1.461(3) . ?
N6 C9 1.442(3) . ?
N6 C25 1.448(3) . ?
N6 C8 1.451(3) . ?
N7 C10 1.349(3) . ?
N7 C11 1.397(3) . ?
N7 C26 1.459(3) . ?
N8 C20 1.455(3) . ?
C2 C3 1.543(3) . ?
C2 H2A 1.0000 . ?
C3 H3A 1.0000 . ?
C5 C6 1.539(3) . ?
C6 C7 1.564(3) . ?
C6 C9 1.574(3) . ?
C7 C17 1.501(3) . ?
C7 C8 1.519(3) . ?
C7 H7A 1.0000 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C16 1.503(3) . ?
C9 C10 1.556(3) . ?
C11 C12 1.380(3) . ?
C11 C16 1.386(3) . ?
C12 C13 1.388(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.376(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.390(3) . ?
C15 C16 1.373(3) . ?
C15 H15A 0.9500 . ?
C17 C18 1.386(3) . ?
C17 C22 1.391(3) . ?
C18 C19 1.376(4) . ?
C18 H18A 0.9500 . ?
C19 C20 1.376(4) . ?
C19 H19A 0.9500 . ?
C20 C21 1.370(4) . ?
C21 C22 1.376(3) . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9500 . ?
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 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.505(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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
C4 S1 C6 90.52(10) . . ?
C1 N1 C23 122.6(2) . . ?
C1 N1 C2 113.1(2) . . ?
C23 N1 C2 121.4(2) . . ?
C1 N2 C3 111.5(2) . . ?
C1 N2 C24 120.6(2) . . ?
C3 N2 C24 123.7(2) . . ?
N4 N3 C2 116.6(2) . . ?
N4 N3 H3N 108(2) . . ?
C2 N3 H3N 111(2) . . ?
C4 N4 N3 111.1(2) . . ?
C5 N5 C4 115.81(19) . . ?
C5 N5 C3 123.33(19) . . ?
C4 N5 C3 117.68(19) . . ?
C9 N6 C25 116.1(2) . . ?
C9 N6 C8 106.68(18) . . ?
C25 N6 C8 113.84(19) . . ?
C10 N7 C11 111.1(2) . . ?
C10 N7 C26 123.9(2) . . ?
C11 N7 C26 124.9(2) . . ?
O5 N8 O4 123.7(2) . . ?
O5 N8 C20 118.4(2) . . ?
O4 N8 C20 117.9(2) . . ?
O1 C1 N1 126.8(3) . . ?
O1 C1 N2 124.7(3) . . ?
N1 C1 N2 108.5(2) . . ?
N3 C2 N1 114.6(2) . . ?
N3 C2 C3 111.0(2) . . ?
N1 C2 C3 102.6(2) . . ?
N3 C2 H2A 109.5 . . ?
N1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
N2 C3 N5 110.9(2) . . ?
N2 C3 C2 104.0(2) . . ?
N5 C3 C2 108.6(2) . . ?
N2 C3 H3A 111.0 . . ?
N5 C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
N4 C4 N5 123.2(2) . . ?
N4 C4 S1 125.99(19) . . ?
N5 C4 S1 110.73(17) . . ?
O2 C5 N5 124.6(2) . . ?
O2 C5 C6 123.9(2) . . ?
N5 C5 C6 111.52(19) . . ?
C5 C6 C7 108.51(18) . . ?
C5 C6 C9 110.65(18) . . ?
C7 C6 C9 104.10(17) . . ?
C5 C6 S1 104.62(15) . . ?
C7 C6 S1 116.17(16) . . ?
C9 C6 S1 112.81(15) . . ?
C17 C7 C8 113.99(19) . . ?
C17 C7 C6 116.67(19) . . ?
C8 C7 C6 104.10(18) . . ?
C17 C7 H7A 107.2 . . ?
C8 C7 H7A 107.2 . . ?
C6 C7 H7A 107.2 . . ?
N6 C8 C7 102.96(18) . . ?
N6 C8 H8A 111.2 . . ?
C7 C8 H8A 111.2 . . ?
N6 C8 H8B 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
N6 C9 C16 114.66(19) . . ?
N6 C9 C10 116.02(19) . . ?
C16 C9 C10 101.00(18) . . ?
N6 C9 C6 101.78(17) . . ?
C16 C9 C6 115.68(18) . . ?
C10 C9 C6 108.14(18) . . ?
O3 C10 N7 125.6(2) . . ?
O3 C10 C9 126.0(2) . . ?
N7 C10 C9 108.3(2) . . ?
C12 C11 C16 122.0(2) . . ?
C12 C11 N7 127.8(2) . . ?
C16 C11 N7 110.1(2) . . ?
C11 C12 C13 117.4(2) . . ?
C11 C12 H12A 121.3 . . ?
C13 C12 H12A 121.3 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C15 122.2(2) . . ?
C13 C14 Br1 119.02(19) . . ?
C15 C14 Br1 118.77(19) . . ?
C16 C15 C14 117.3(2) . . ?
C16 C15 H15A 121.3 . . ?
C14 C15 H15A 121.3 . . ?
C15 C16 C11 120.7(2) . . ?
C15 C16 C9 130.3(2) . . ?
C11 C16 C9 109.0(2) . . ?
C18 C17 C22 119.2(2) . . ?
C18 C17 C7 119.3(2) . . ?
C22 C17 C7 121.5(2) . . ?
C19 C18 C17 121.0(2) . . ?
C19 C18 H18A 119.5 . . ?
C17 C18 H18A 119.5 . . ?
C20 C19 C18 117.9(2) . . ?
C20 C19 H19A 121.0 . . ?
C18 C19 H19A 121.0 . . ?
C21 C20 C19 122.9(2) . . ?
C21 C20 N8 117.8(2) . . ?
C19 C20 N8 119.2(2) . . ?
C20 C21 C22 118.5(2) . . ?
C20 C21 H21A 120.7 . . ?
C22 C21 H21A 120.7 . . ?
C21 C22 C17 120.4(2) . . ?
C21 C22 H22A 119.8 . . ?
C17 C22 H22A 119.8 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N6 C25 H25A 109.5 . . ?
N6 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N6 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N7 C26 C27 110.6(2) . . ?
N7 C26 H26A 109.5 . . ?
C27 C26 H26A 109.5 . . ?
N7 C26 H26B 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

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
C2 N3 N4 C4 50.4(3) . . . . ?
C23 N1 C1 O1 -20.9(4) . . . . ?
C2 N1 C1 O1 178.0(2) . . . . ?
C23 N1 C1 N2 158.3(3) . . . . ?
C2 N1 C1 N2 -2.8(3) . . . . ?
C3 N2 C1 O1 -174.8(2) . . . . ?
C24 N2 C1 O1 -17.1(4) . . . . ?
C3 N2 C1 N1 5.9(3) . . . . ?
C24 N2 C1 N1 163.6(2) . . . . ?
N4 N3 C2 N1 63.3(3) . . . . ?
N4 N3 C2 C3 -52.4(3) . . . . ?
C1 N1 C2 N3 -121.5(2) . . . . ?
C23 N1 C2 N3 77.1(3) . . . . ?
C1 N1 C2 C3 -1.1(3) . . . . ?
C23 N1 C2 C3 -162.5(2) . . . . ?
C1 N2 C3 N5 110.2(2) . . . . ?
C24 N2 C3 N5 -46.7(3) . . . . ?
C1 N2 C3 C2 -6.4(3) . . . . ?
C24 N2 C3 C2 -163.3(2) . . . . ?
C5 N5 C3 N2 78.3(3) . . . . ?
C4 N5 C3 N2 -80.7(3) . . . . ?
C5 N5 C3 C2 -168.1(2) . . . . ?
C4 N5 C3 C2 33.0(3) . . . . ?
N3 C2 C3 N2 127.3(2) . . . . ?
N1 C2 C3 N2 4.4(2) . . . . ?
N3 C2 C3 N5 9.1(3) . . . . ?
N1 C2 C3 N5 -113.8(2) . . . . ?
N3 N4 C4 N5 -2.9(3) . . . . ?
N3 N4 C4 S1 174.19(18) . . . . ?
C5 N5 C4 N4 159.1(2) . . . . ?
C3 N5 C4 N4 -40.3(3) . . . . ?
C5 N5 C4 S1 -18.3(3) . . . . ?
C3 N5 C4 S1 142.23(18) . . . . ?
C6 S1 C4 N4 -153.5(2) . . . . ?
C6 S1 C4 N5 23.85(18) . . . . ?
C4 N5 C5 O2 -179.4(2) . . . . ?
C3 N5 C5 O2 21.3(4) . . . . ?
C4 N5 C5 C6 0.1(3) . . . . ?
C3 N5 C5 C6 -159.3(2) . . . . ?
O2 C5 C6 C7 -39.2(3) . . . . ?
N5 C5 C6 C7 141.35(19) . . . . ?
O2 C5 C6 C9 74.4(3) . . . . ?
N5 C5 C6 C9 -105.0(2) . . . . ?
O2 C5 C6 S1 -163.8(2) . . . . ?
N5 C5 C6 S1 16.7(2) . . . . ?
C4 S1 C6 C5 -22.28(16) . . . . ?
C4 S1 C6 C7 -141.87(18) . . . . ?
C4 S1 C6 C9 98.05(17) . . . . ?
C5 C6 C7 C17 -111.9(2) . . . . ?
C9 C6 C7 C17 130.2(2) . . . . ?
S1 C6 C7 C17 5.6(3) . . . . ?
C5 C6 C7 C8 121.57(19) . . . . ?
C9 C6 C7 C8 3.7(2) . . . . ?
S1 C6 C7 C8 -120.97(17) . . . . ?
C9 N6 C8 C7 46.1(2) . . . . ?
C25 N6 C8 C7 175.4(2) . . . . ?
C17 C7 C8 N6 -156.79(19) . . . . ?
C6 C7 C8 N6 -28.6(2) . . . . ?
C25 N6 C9 C16 63.6(3) . . . . ?
C8 N6 C9 C16 -168.37(19) . . . . ?
C25 N6 C9 C10 -53.7(3) . . . . ?
C8 N6 C9 C10 74.4(2) . . . . ?
C25 N6 C9 C6 -170.8(2) . . . . ?
C8 N6 C9 C6 -42.7(2) . . . . ?
C5 C6 C9 N6 -93.9(2) . . . . ?
C7 C6 C9 N6 22.5(2) . . . . ?
S1 C6 C9 N6 149.29(15) . . . . ?
C5 C6 C9 C16 31.1(3) . . . . ?
C7 C6 C9 C16 147.47(19) . . . . ?
S1 C6 C9 C16 -85.7(2) . . . . ?
C5 C6 C9 C10 143.43(19) . . . . ?
C7 C6 C9 C10 -100.2(2) . . . . ?
S1 C6 C9 C10 26.6(2) . . . . ?
C11 N7 C10 O3 175.6(2) . . . . ?
C26 N7 C10 O3 -7.5(4) . . . . ?
C11 N7 C10 C9 -6.0(3) . . . . ?
C26 N7 C10 C9 170.9(2) . . . . ?
N6 C9 C10 O3 -49.7(3) . . . . ?
C16 C9 C10 O3 -174.3(2) . . . . ?
C6 C9 C10 O3 63.8(3) . . . . ?
N6 C9 C10 N7 131.8(2) . . . . ?
C16 C9 C10 N7 7.2(2) . . . . ?
C6 C9 C10 N7 -114.6(2) . . . . ?
C10 N7 C11 C12 -173.3(2) . . . . ?
C26 N7 C11 C12 9.8(4) . . . . ?
C10 N7 C11 C16 2.0(3) . . . . ?
C26 N7 C11 C16 -174.9(2) . . . . ?
C16 C11 C12 C13 -0.2(4) . . . . ?
N7 C11 C12 C13 174.6(2) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C12 C13 C14 Br1 -179.0(2) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
Br1 C14 C15 C16 179.93(18) . . . . ?
C14 C15 C16 C11 -1.4(4) . . . . ?
C14 C15 C16 C9 -178.2(2) . . . . ?
C12 C11 C16 C15 1.2(4) . . . . ?
N7 C11 C16 C15 -174.4(2) . . . . ?
C12 C11 C16 C9 178.7(2) . . . . ?
N7 C11 C16 C9 3.0(3) . . . . ?
N6 C9 C16 C15 45.6(3) . . . . ?
C10 C9 C16 C15 171.1(2) . . . . ?
C6 C9 C16 C15 -72.4(3) . . . . ?
N6 C9 C16 C11 -131.6(2) . . . . ?
C10 C9 C16 C11 -6.0(2) . . . . ?
C6 C9 C16 C11 110.4(2) . . . . ?
C8 C7 C17 C18 -120.6(2) . . . . ?
C6 C7 C17 C18 118.0(2) . . . . ?
C8 C7 C17 C22 57.7(3) . . . . ?
C6 C7 C17 C22 -63.8(3) . . . . ?
C22 C17 C18 C19 -1.4(4) . . . . ?
C7 C17 C18 C19 176.9(2) . . . . ?
C17 C18 C19 C20 1.7(4) . . . . ?
C18 C19 C20 C21 -0.3(4) . . . . ?
C18 C19 C20 N8 -176.4(2) . . . . ?
O5 N8 C20 C21 19.6(3) . . . . ?
O4 N8 C20 C21 -160.2(3) . . . . ?
O5 N8 C20 C19 -164.1(2) . . . . ?
O4 N8 C20 C19 16.2(4) . . . . ?
C19 C20 C21 C22 -1.2(4) . . . . ?
N8 C20 C21 C22 175.0(2) . . . . ?
C20 C21 C22 C17 1.4(4) . . . . ?
C18 C17 C22 C21 -0.1(4) . . . . ?
C7 C17 C22 C21 -178.4(2) . . . . ?
C10 N7 C26 C27 -92.9(3) . . . . ?
C11 N7 C26 C27 83.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3N O1 0.81(3) 2.31(3) 2.994(3) 142(3) 2_455
N3 H3N O5 0.81(3) 2.63(3) 3.204(3) 129(3) 2

_refine_diff_density_max         0.918
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.086



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dv64
_database_code_depnum_ccdc_archive 'CCDC 1981084'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2020-01-31 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C27 H28 F N7 O3 S), C H4 O, H2 O'
_chemical_formula_sum            'C27.50 H31 F N7 O4 S'
_chemical_formula_weight         574.65

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.4741(4)
_cell_length_b                   13.4934(4)
_cell_length_c                   15.7758(5)
_cell_angle_alpha                84.2195(7)
_cell_angle_beta                 85.3686(7)
_cell_angle_gamma                76.9008(7)
_cell_volume                     2774.41(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.171
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6959
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38708
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.940
_diffrn_reflns_theta_max         30.548
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             16974
_reflns_number_gt                13265
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0549P)²+0.7437P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         16974
_refine_ls_number_parameters     765
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.79660(3) 0.19911(2) 0.18969(2) 0.01615(7) Uani 1 1 d . . . . .
F1 F 0.57985(10) 0.11997(9) 0.37406(8) 0.0557(4) Uani 1 1 d . . . . .
O1 O 0.72436(7) -0.22328(8) 0.16530(6) 0.0215(2) Uani 1 1 d . . . . .
O2 O 0.82302(7) 0.09535(7) 0.42575(6) 0.01776(18) Uani 1 1 d . . . . .
O3 O 0.83474(8) 0.40770(7) 0.18521(6) 0.0224(2) Uani 1 1 d . . . . .
N1 N 0.81038(8) -0.16186(8) 0.26293(7) 0.0154(2) Uani 1 1 d . . . . .
N2 N 0.86722(8) -0.15803(8) 0.12578(7) 0.0141(2) Uani 1 1 d . . . . .
N3 N 0.91033(8) -0.06051(8) 0.32225(7) 0.0148(2) Uani 1 1 d . . . . .
H3N H 0.9722(14) -0.0629(13) 0.3356(11) 0.024(4) Uiso 1 1 d . . . . .
N4 N 0.86789(8) 0.04155(8) 0.29234(6) 0.01338(19) Uani 1 1 d . . . . .
N5 N 0.87842(8) 0.01225(8) 0.14526(7) 0.0139(2) Uani 1 1 d . . . . .
N6 N 0.80500(9) 0.36212(9) 0.37893(7) 0.0174(2) Uani 1 1 d . . . . .
N7 N 0.99738(9) 0.31781(9) 0.21370(8) 0.0205(2) Uani 1 1 d . . . . .
H7N H 1.0295(15) 0.3386(15) 0.1679(13) 0.035(5) Uiso 1 1 d . . . . .
C1 C 0.79364(9) -0.18427(9) 0.18341(8) 0.0153(2) Uani 1 1 d . . . . .
C2 C 0.90859(9) -0.13307(9) 0.26101(8) 0.0140(2) Uani 1 1 d . . . . .
H2A H 0.962321 -0.196013 0.274410 0.017 Uiso 1 1 calc R U . . .
C3 C 0.92359(9) -0.09694(9) 0.16554(8) 0.0130(2) Uani 1 1 d . . . . .
H3A H 0.997476 -0.113570 0.145964 0.016 Uiso 1 1 calc R U . . .
C4 C 0.85527(9) 0.06961(9) 0.20640(8) 0.0128(2) Uani 1 1 d . . . . .
C5 C 0.82807(9) 0.11379(9) 0.34896(8) 0.0137(2) Uani 1 1 d . . . . .
C6 C 0.79408(9) 0.22053(9) 0.30263(7) 0.0137(2) Uani 1 1 d . . . . .
C7 C 0.68632(10) 0.27591(10) 0.34088(8) 0.0158(2) Uani 1 1 d . . . . .
H7A H 0.676249 0.240833 0.398822 0.019 Uiso 1 1 calc R U . . .
C8 C 0.69962(10) 0.38234(10) 0.35445(9) 0.0188(2) Uani 1 1 d . . . . .
H8A H 0.689852 0.428321 0.301347 0.023 Uiso 1 1 calc R U . . .
H8B H 0.651332 0.412892 0.400346 0.023 Uiso 1 1 calc R U . . .
C9 C 0.86714(10) 0.29400(10) 0.31892(8) 0.0149(2) Uani 1 1 d . . . . .
C10 C 0.89499(10) 0.34876(10) 0.23047(8) 0.0175(2) Uani 1 1 d . . . . .
C11 C 1.04469(11) 0.25632(10) 0.28298(9) 0.0201(3) Uani 1 1 d . . . . .
C12 C 1.14798(11) 0.21629(12) 0.29153(11) 0.0277(3) Uani 1 1 d . . . . .
H12A H 1.196969 0.224231 0.246035 0.033 Uiso 1 1 calc R U . . .
C13 C 1.17713(12) 0.16399(12) 0.36939(12) 0.0309(3) Uani 1 1 d . . . . .
H13A H 1.247209 0.133884 0.376335 0.037 Uiso 1 1 calc R U . . .
C14 C 1.10662(12) 0.15470(11) 0.43698(11) 0.0278(3) Uani 1 1 d . . . . .
H14A H 1.128969 0.121079 0.490158 0.033 Uiso 1 1 calc R U . . .
C15 C 1.00248(11) 0.19475(11) 0.42708(9) 0.0223(3) Uani 1 1 d . . . . .
H15A H 0.953732 0.188899 0.473226 0.027 Uiso 1 1 calc R U . . .
C16 C 0.97176(10) 0.24309(10) 0.34877(8) 0.0173(2) Uani 1 1 d . . . . .
C17 C 0.59641(10) 0.27119(10) 0.29158(8) 0.0176(2) Uani 1 1 d . . . . .
C18 C 0.54635(12) 0.19208(12) 0.30996(10) 0.0280(3) Uani 1 1 d . . . . .
C19 C 0.46427(13) 0.18140(15) 0.26707(12) 0.0362(4) Uani 1 1 d . . . . .
H19A H 0.433346 0.124777 0.281314 0.043 Uiso 1 1 calc R U . . .
C20 C 0.42862(12) 0.25520(13) 0.20310(11) 0.0320(3) Uani 1 1 d . . . . .
H20A H 0.371622 0.250383 0.173287 0.038 Uiso 1 1 calc R U . . .
C21 C 0.47552(13) 0.33610(12) 0.18224(11) 0.0328(4) Uani 1 1 d . . . . .
H21A H 0.450901 0.386726 0.138000 0.039 Uiso 1 1 calc R U . . .
C22 C 0.55889(12) 0.34353(11) 0.22600(10) 0.0276(3) Uani 1 1 d . . . . .
H22A H 0.590876 0.399247 0.210736 0.033 Uiso 1 1 calc R U . . .
C23 C 0.76313(11) -0.20340(11) 0.34096(9) 0.0213(3) Uani 1 1 d . . . . .
H23A H 0.816083 -0.231379 0.382284 0.026 Uiso 1 1 calc R U . . .
H23B H 0.733054 -0.260093 0.327640 0.026 Uiso 1 1 calc R U . . .
C24 C 0.68029(12) -0.12242(14) 0.38118(10) 0.0312(3) Uani 1 1 d . . . . .
H24A H 0.645683 -0.154224 0.429971 0.047 Uiso 1 1 calc R U . . .
H24B H 0.630662 -0.090675 0.338888 0.047 Uiso 1 1 calc R U . . .
H24C H 0.711180 -0.070193 0.400576 0.047 Uiso 1 1 calc R U . . .
C25 C 0.84685(10) -0.14184(10) 0.03477(8) 0.0170(2) Uani 1 1 d . . . . .
H25A H 0.792303 -0.079630 0.025277 0.020 Uiso 1 1 calc R U . . .
H25B H 0.821832 -0.200409 0.018453 0.020 Uiso 1 1 calc R U . . .
C26 C 0.94078(11) -0.13038(12) -0.02202(9) 0.0227(3) Uani 1 1 d . . . . .
H26A H 0.924024 -0.122505 -0.081977 0.034 Uiso 1 1 calc R U . . .
H26B H 0.995486 -0.191244 -0.012165 0.034 Uiso 1 1 calc R U . . .
H26C H 0.963439 -0.069994 -0.008552 0.034 Uiso 1 1 calc R U . . .
C27 C 0.84143(12) 0.45496(11) 0.38720(9) 0.0245(3) Uani 1 1 d . . . . .
H27A H 0.912004 0.436224 0.404389 0.037 Uiso 1 1 calc R U . . .
H27B H 0.798069 0.494544 0.430483 0.037 Uiso 1 1 calc R U . . .
H27C H 0.838587 0.496180 0.332271 0.037 Uiso 1 1 calc R U . . .
S1A S 0.39111(2) 0.59937(3) 0.22037(2) 0.01716(7) Uani 1 1 d . . . . .
F1A F 0.10358(9) 0.56369(9) 0.37073(8) 0.0494(3) Uani 1 1 d . . . . .
O1A O 0.12287(8) 0.37327(7) 0.07615(6) 0.0210(2) Uani 1 1 d . . . . .
O2A O 0.14302(7) 0.80950(7) 0.23285(6) 0.01856(19) Uani 1 1 d . . . . .
O3A O 0.51593(7) 0.66832(8) 0.34341(6) 0.0234(2) Uani 1 1 d . . . . .
N1A N 0.10427(8) 0.54821(8) 0.08106(7) 0.0164(2) Uani 1 1 d . . . . .
N2A N 0.23770(9) 0.46201(8) 0.00618(7) 0.0169(2) Uani 1 1 d . . . . .
N3A N 0.15054(8) 0.71118(8) 0.08456(7) 0.0155(2) Uani 1 1 d . . . . .
H3NA H 0.1672(13) 0.7619(14) 0.0503(11) 0.022(4) Uiso 1 1 d . . . . .
N4A N 0.22497(8) 0.68599(8) 0.14650(6) 0.0137(2) Uani 1 1 d . . . . .
N5A N 0.33630(8) 0.55480(8) 0.07276(7) 0.0165(2) Uani 1 1 d . . . . .
N6A N 0.31258(8) 0.82408(8) 0.37199(6) 0.0150(2) Uani 1 1 d . . . . .
N7A N 0.52890(9) 0.79286(10) 0.23467(7) 0.0205(2) Uani 1 1 d . . . . .
H7NA H 0.5945(16) 0.7773(16) 0.2220(13) 0.041(6) Uiso 1 1 d . . . . .
C1A C 0.15228(10) 0.45358(10) 0.05670(8) 0.0161(2) Uani 1 1 d . . . . .
C2A C 0.15259(10) 0.62536(10) 0.03480(8) 0.0156(2) Uani 1 1 d . . . . .
H2AA H 0.115889 0.651599 -0.018323 0.019 Uiso 1 1 calc R U . . .
C3A C 0.25942(10) 0.56222(10) 0.00956(8) 0.0159(2) Uani 1 1 d . . . . .
H3AA H 0.284417 0.588351 -0.047918 0.019 Uiso 1 1 calc R U . . .
C4A C 0.31309(9) 0.61079(9) 0.13446(8) 0.0141(2) Uani 1 1 d . . . . .
C5A C 0.21505(9) 0.74045(10) 0.21668(8) 0.0139(2) Uani 1 1 d . . . . .
C6A C 0.30503(9) 0.70232(10) 0.27414(8) 0.0138(2) Uani 1 1 d . . . . .
C7A C 0.25952(10) 0.67091(10) 0.36642(8) 0.0160(2) Uani 1 1 d . . . . .
H7AA H 0.184005 0.698139 0.367046 0.019 Uiso 1 1 calc R U . . .
C8A C 0.30126(10) 0.73186(10) 0.42623(8) 0.0168(2) Uani 1 1 d . . . . .
H8AA H 0.252853 0.749097 0.475949 0.020 Uiso 1 1 calc R U . . .
H8AB H 0.367786 0.693423 0.446810 0.020 Uiso 1 1 calc R U . . .
C9A C 0.36074(9) 0.78936(10) 0.28991(8) 0.0140(2) Uani 1 1 d . . . . .
C10A C 0.47785(10) 0.74039(11) 0.29443(8) 0.0177(2) Uani 1 1 d . . . . .
C11A C 0.46286(10) 0.87470(11) 0.19242(8) 0.0190(3) Uani 1 1 d . . . . .
C12A C 0.48960(12) 0.94900(12) 0.13354(9) 0.0256(3) Uani 1 1 d . . . . .
H12B H 0.558406 0.944865 0.112614 0.031 Uiso 1 1 calc R U . . .
C13A C 0.41188(13) 1.02981(12) 0.10627(9) 0.0272(3) Uani 1 1 d . . . . .
H13B H 0.427675 1.081396 0.065265 0.033 Uiso 1 1 calc R U . . .
C14A C 0.31127(12) 1.03656(11) 0.13797(9) 0.0241(3) Uani 1 1 d . . . . .
H14B H 0.259878 1.093834 0.119949 0.029 Uiso 1 1 calc R U . . .
C15A C 0.28502(11) 0.95965(11) 0.19623(8) 0.0199(3) Uani 1 1 d . . . . .
H15B H 0.216270 0.963821 0.217331 0.024 Uiso 1 1 calc R U . . .
C16A C 0.36147(10) 0.87753(10) 0.22232(8) 0.0163(2) Uani 1 1 d . . . . .
C17A C 0.27659(12) 0.55786(11) 0.39225(8) 0.0225(3) Uani 1 1 d . . . . .
C18A C 0.19683(15) 0.50808(13) 0.39209(10) 0.0329(4) Uani 1 1 d . . . . .
C19A C 0.20653(19) 0.40467(14) 0.41421(12) 0.0460(5) Uani 1 1 d . . . . .
H19B H 0.150379 0.373321 0.412557 0.055 Uiso 1 1 calc R U . . .
C20A C 0.3004(2) 0.34823(14) 0.43880(12) 0.0501(6) Uani 1 1 d . . . . .
H20B H 0.309133 0.276966 0.453960 0.060 Uiso 1 1 calc R U . . .
C21A C 0.38138(17) 0.39445(14) 0.44153(12) 0.0433(5) Uani 1 1 d . . . . .
H21B H 0.445136 0.355199 0.459582 0.052 Uiso 1 1 calc R U . . .
C22A C 0.36987(13) 0.49886(12) 0.41778(10) 0.0311(3) Uani 1 1 d . . . . .
H22B H 0.426282 0.529923 0.419077 0.037 Uiso 1 1 calc R U . . .
C23A C 0.31594(11) 0.37230(11) -0.01444(9) 0.0226(3) Uani 1 1 d . . . . .
H23C H 0.282737 0.318282 -0.028785 0.027 Uiso 1 1 calc R U . . .
H23D H 0.355911 0.345735 0.036158 0.027 Uiso 1 1 calc R U . . .
C24A C 0.38717(14) 0.39679(13) -0.08867(12) 0.0370(4) Uani 1 1 d . . . . .
H24D H 0.436364 0.334247 -0.102639 0.056 Uiso 1 1 calc R U . . .
H24E H 0.423780 0.446718 -0.073156 0.056 Uiso 1 1 calc R U . . .
H24F H 0.347547 0.425275 -0.138329 0.056 Uiso 1 1 calc R U . . .
C25A C -0.00366(10) 0.57291(10) 0.11070(9) 0.0192(3) Uani 1 1 d . . . . .
H25C H -0.035511 0.516168 0.100618 0.023 Uiso 1 1 calc R U . . .
H25D H -0.038899 0.635020 0.077065 0.023 Uiso 1 1 calc R U . . .
C26A C -0.01811(12) 0.59064(11) 0.20451(9) 0.0245(3) Uani 1 1 d . . . . .
H26D H -0.091207 0.608087 0.221230 0.037 Uiso 1 1 calc R U . . .
H26E H 0.013139 0.646886 0.214812 0.037 Uiso 1 1 calc R U . . .
H26F H 0.014364 0.528448 0.238258 0.037 Uiso 1 1 calc R U . . .
C27A C 0.36661(11) 0.88835(11) 0.41232(9) 0.0208(3) Uani 1 1 d . . . . .
H27D H 0.326832 0.913285 0.463700 0.031 Uiso 1 1 calc R U . . .
H27E H 0.375296 0.946549 0.372214 0.031 Uiso 1 1 calc R U . . .
H27F H 0.433734 0.848081 0.427963 0.031 Uiso 1 1 calc R U . . .
O1S O 0.77645(9) 0.12569(8) 0.00434(7) 0.0271(2) Uani 1 1 d . . . . .
H1SO H 0.8093(17) 0.0877(17) 0.0420(14) 0.044(6) Uiso 1 1 d . . . . .
C1S C 0.66962(13) 0.14463(13) 0.02391(11) 0.0329(3) Uani 1 1 d . . . . .
H1SA H 0.634321 0.147557 -0.028528 0.049 Uiso 1 1 calc R U . . .
H1SB H 0.647192 0.209866 0.049497 0.049 Uiso 1 1 calc R U . . .
H1SC H 0.653492 0.089565 0.064273 0.049 Uiso 1 1 calc R U . . .
O2S O 0.09937(8) 0.92487(9) 0.39175(7) 0.0257(2) Uani 1 1 d . . . . .
H2SA H 0.1589(18) 0.8995(17) 0.3760(14) 0.045(6) Uiso 1 1 d . . . . .
H2SB H 0.106(2) 0.955(2) 0.4365(19) 0.079(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C4 1.7499(12) . ?
S1 C6 1.8300(12) . ?
F1 C18 1.3599(18) . ?
O1 C1 1.2354(15) . ?
O2 C5 1.2115(15) . ?
O3 C10 1.2198(16) . ?
N1 C1 1.3670(16) . ?
N1 C2 1.4586(16) . ?
N1 C23 1.4598(16) . ?
N2 C1 1.3724(16) . ?
N2 C3 1.4543(15) . ?
N2 C25 1.4689(16) . ?
N3 N4 1.4148(14) . ?
N3 C2 1.4482(16) . ?
N3 H3N 0.869(18) . ?
N4 C5 1.3773(16) . ?
N4 C4 1.3839(15) . ?
N5 C4 1.2724(16) . ?
N5 C3 1.4743(15) . ?
N6 C8 1.4599(17) . ?
N6 C9 1.4631(16) . ?
N6 C27 1.4661(17) . ?
N7 C10 1.3602(18) . ?
N7 C11 1.4070(19) . ?
N7 H7N 0.87(2) . ?
C2 C3 1.5473(17) . ?
C2 H2A 1.0000 . ?
C3 H3A 1.0000 . ?
C5 C6 1.5367(17) . ?
C6 C7 1.5774(17) . ?
C6 C9 1.5976(17) . ?
C7 C17 1.5079(18) . ?
C7 C8 1.5248(18) . ?
C7 H7A 1.0000 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C16 1.5112(18) . ?
C9 C10 1.5708(17) . ?
C11 C12 1.386(2) . ?
C11 C16 1.3972(18) . ?
C12 C13 1.392(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.385(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.400(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3859(19) . ?
C15 H15A 0.9500 . ?
C17 C18 1.382(2) . ?
C17 C22 1.391(2) . ?
C18 C19 1.384(2) . ?
C19 C20 1.378(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.381(2) . ?
C20 H20A 0.9500 . ?
C21 C22 1.392(2) . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9500 . ?
C23 C24 1.521(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.5185(18) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
S1A C4A 1.7551(13) . ?
S1A C6A 1.8283(12) . ?
F1A C18A 1.358(2) . ?
O1A C1A 1.2383(16) . ?
O2A C5A 1.2138(15) . ?
O3A C10A 1.2216(17) . ?
N1A C1A 1.3715(16) . ?
N1A C2A 1.4552(17) . ?
N1A C25A 1.4651(17) . ?
N2A C1A 1.3659(16) . ?
N2A C3A 1.4538(16) . ?
N2A C23A 1.4587(17) . ?
N3A N4A 1.4189(14) . ?
N3A C2A 1.4570(16) . ?
N3A H3NA 0.887(18) . ?
N4A C5A 1.3708(16) . ?
N4A C4A 1.3899(16) . ?
N5A C4A 1.2679(16) . ?
N5A C3A 1.4754(16) . ?
N6A C8A 1.4679(17) . ?
N6A C27A 1.4693(16) . ?
N6A C9A 1.4717(15) . ?
N7A C10A 1.3582(18) . ?
N7A C11A 1.3991(19) . ?
N7A H7NA 0.87(2) . ?
C2A C3A 1.5416(18) . ?
C2A H2AA 1.0000 . ?
C3A H3AA 1.0000 . ?
C5A C6A 1.5353(17) . ?
C6A C9A 1.5791(17) . ?
C6A C7A 1.5888(17) . ?
C7A C17A 1.5088(19) . ?
C7A C8A 1.5280(18) . ?
C7A H7AA 1.0000 . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A C16A 1.5167(18) . ?
C9A C10A 1.5709(17) . ?
C11A C12A 1.386(2) . ?
C11A C16A 1.4022(18) . ?
C12A C13A 1.390(2) . ?
C12A H12B 0.9500 . ?
C13A C14A 1.393(2) . ?
C13A H13B 0.9500 . ?
C14A C15A 1.403(2) . ?
C14A H14B 0.9500 . ?
C15A C16A 1.3847(19) . ?
C15A H15B 0.9500 . ?
C17A C18A 1.391(2) . ?
C17A C22A 1.393(2) . ?
C18A C19A 1.383(2) . ?
C19A C20A 1.383(3) . ?
C19A H19B 0.9500 . ?
C20A C21A 1.380(3) . ?
C20A H20B 0.9500 . ?
C21A C22A 1.398(2) . ?
C21A H21B 0.9500 . ?
C22A H22B 0.9500 . ?
C23A C24A 1.512(2) . ?
C23A H23C 0.9900 . ?
C23A H23D 0.9900 . ?
C24A H24D 0.9800 . ?
C24A H24E 0.9800 . ?
C24A H24F 0.9800 . ?
C25A C26A 1.513(2) . ?
C25A H25C 0.9900 . ?
C25A H25D 0.9900 . ?
C26A H26D 0.9800 . ?
C26A H26E 0.9800 . ?
C26A H26F 0.9800 . ?
C27A H27D 0.9800 . ?
C27A H27E 0.9800 . ?
C27A H27F 0.9800 . ?
O1S C1S 1.418(2) . ?
O1S H1SO 0.83(2) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
O2S H2SA 0.83(2) . ?
O2S H2SB 0.87(3) . ?

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
C4 S1 C6 93.40(6) . . ?
C1 N1 C2 109.64(10) . . ?
C1 N1 C23 122.88(11) . . ?
C2 N1 C23 122.33(10) . . ?
C1 N2 C3 109.37(10) . . ?
C1 N2 C25 118.82(10) . . ?
C3 N2 C25 122.57(10) . . ?
N4 N3 C2 113.02(10) . . ?
N4 N3 H3N 107.3(12) . . ?
C2 N3 H3N 111.4(12) . . ?
C5 N4 C4 117.72(10) . . ?
C5 N4 N3 120.56(10) . . ?
C4 N4 N3 121.38(10) . . ?
C4 N5 C3 118.31(10) . . ?
C8 N6 C9 107.28(10) . . ?
C8 N6 C27 113.51(11) . . ?
C9 N6 C27 114.48(10) . . ?
C10 N7 C11 111.50(11) . . ?
C10 N7 H7N 123.5(13) . . ?
C11 N7 H7N 124.7(13) . . ?
O1 C1 N1 126.05(12) . . ?
O1 C1 N2 124.55(12) . . ?
N1 C1 N2 109.40(10) . . ?
N3 C2 N1 112.72(10) . . ?
N3 C2 C3 116.90(10) . . ?
N1 C2 C3 101.36(9) . . ?
N3 C2 H2A 108.5 . . ?
N1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
N2 C3 N5 109.27(10) . . ?
N2 C3 C2 101.38(9) . . ?
N5 C3 C2 113.43(10) . . ?
N2 C3 H3A 110.8 . . ?
N5 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
N5 C4 N4 127.26(11) . . ?
N5 C4 S1 121.91(9) . . ?
N4 C4 S1 110.80(9) . . ?
O2 C5 N4 123.89(12) . . ?
O2 C5 C6 124.55(11) . . ?
N4 C5 C6 111.54(10) . . ?
C5 C6 C7 110.39(10) . . ?
C5 C6 C9 111.61(10) . . ?
C7 C6 C9 103.67(9) . . ?
C5 C6 S1 105.22(8) . . ?
C7 C6 S1 114.14(8) . . ?
C9 C6 S1 111.98(8) . . ?
C17 C7 C8 116.28(11) . . ?
C17 C7 C6 115.60(10) . . ?
C8 C7 C6 104.12(10) . . ?
C17 C7 H7A 106.7 . . ?
C8 C7 H7A 106.7 . . ?
C6 C7 H7A 106.7 . . ?
N6 C8 C7 102.36(10) . . ?
N6 C8 H8A 111.3 . . ?
C7 C8 H8A 111.3 . . ?
N6 C8 H8B 111.3 . . ?
C7 C8 H8B 111.3 . . ?
H8A C8 H8B 109.2 . . ?
N6 C9 C16 113.68(10) . . ?
N6 C9 C10 114.52(10) . . ?
C16 C9 C10 101.45(10) . . ?
N6 C9 C6 102.94(10) . . ?
C16 C9 C6 116.76(10) . . ?
C10 C9 C6 107.84(10) . . ?
O3 C10 N7 126.68(12) . . ?
O3 C10 C9 125.63(12) . . ?
N7 C10 C9 107.69(11) . . ?
C12 C11 C16 121.78(14) . . ?
C12 C11 N7 128.05(13) . . ?
C16 C11 N7 110.10(12) . . ?
C11 C12 C13 117.42(14) . . ?
C11 C12 H12A 121.3 . . ?
C13 C12 H12A 121.3 . . ?
C14 C13 C12 121.72(14) . . ?
C14 C13 H13A 119.1 . . ?
C12 C13 H13A 119.1 . . ?
C13 C14 C15 120.13(14) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C16 C15 C14 118.84(14) . . ?
C16 C15 H15A 120.6 . . ?
C14 C15 H15A 120.6 . . ?
C15 C16 C11 119.95(13) . . ?
C15 C16 C9 131.23(12) . . ?
C11 C16 C9 108.71(11) . . ?
C18 C17 C22 116.01(13) . . ?
C18 C17 C7 120.51(12) . . ?
C22 C17 C7 123.48(12) . . ?
F1 C18 C17 118.10(13) . . ?
F1 C18 C19 117.79(14) . . ?
C17 C18 C19 124.11(15) . . ?
C20 C19 C18 118.15(16) . . ?
C20 C19 H19A 120.9 . . ?
C18 C19 H19A 120.9 . . ?
C19 C20 C21 120.18(15) . . ?
C19 C20 H20A 119.9 . . ?
C21 C20 H20A 119.9 . . ?
C20 C21 C22 120.04(15) . . ?
C20 C21 H21A 120.0 . . ?
C22 C21 H21A 120.0 . . ?
C17 C22 C21 121.48(15) . . ?
C17 C22 H22A 119.3 . . ?
C21 C22 H22A 119.3 . . ?
N1 C23 C24 111.65(12) . . ?
N1 C23 H23A 109.3 . . ?
C24 C23 H23A 109.3 . . ?
N1 C23 H23B 109.3 . . ?
C24 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N2 C25 C26 112.59(11) . . ?
N2 C25 H25A 109.1 . . ?
C26 C25 H25A 109.1 . . ?
N2 C25 H25B 109.1 . . ?
C26 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N6 C27 H27A 109.5 . . ?
N6 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N6 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C4A S1A C6A 93.74(6) . . ?
C1A N1A C2A 109.57(10) . . ?
C1A N1A C25A 122.50(11) . . ?
C2A N1A C25A 121.07(11) . . ?
C1A N2A C3A 110.23(10) . . ?
C1A N2A C23A 121.52(11) . . ?
C3A N2A C23A 123.05(11) . . ?
N4A N3A C2A 111.56(10) . . ?
N4A N3A H3NA 105.5(11) . . ?
C2A N3A H3NA 109.1(11) . . ?
C5A N4A C4A 118.37(10) . . ?
C5A N4A N3A 120.56(10) . . ?
C4A N4A N3A 120.90(10) . . ?
C4A N5A C3A 117.98(11) . . ?
C8A N6A C27A 113.02(10) . . ?
C8A N6A C9A 106.35(10) . . ?
C27A N6A C9A 114.41(10) . . ?
C10A N7A C11A 111.81(11) . . ?
C10A N7A H7NA 125.3(14) . . ?
C11A N7A H7NA 122.9(14) . . ?
O1A C1A N2A 125.09(12) . . ?
O1A C1A N1A 125.91(12) . . ?
N2A C1A N1A 109.00(11) . . ?
N1A C2A N3A 112.73(10) . . ?
N1A C2A C3A 102.09(10) . . ?
N3A C2A C3A 115.80(10) . . ?
N1A C2A H2AA 108.6 . . ?
N3A C2A H2AA 108.6 . . ?
C3A C2A H2AA 108.6 . . ?
N2A C3A N5A 108.91(10) . . ?
N2A C3A C2A 101.04(10) . . ?
N5A C3A C2A 114.62(10) . . ?
N2A C3A H3AA 110.6 . . ?
N5A C3A H3AA 110.6 . . ?
C2A C3A H3AA 110.6 . . ?
N5A C4A N4A 127.12(11) . . ?
N5A C4A S1A 122.67(10) . . ?
N4A C4A S1A 110.19(9) . . ?
O2A C5A N4A 124.41(11) . . ?
O2A C5A C6A 123.55(11) . . ?
N4A C5A C6A 112.02(10) . . ?
C5A C6A C9A 112.81(10) . . ?
C5A C6A C7A 107.48(9) . . ?
C9A C6A C7A 103.69(9) . . ?
C5A C6A S1A 105.58(8) . . ?
C9A C6A S1A 111.60(8) . . ?
C7A C6A S1A 115.81(9) . . ?
C17A C7A C8A 114.81(11) . . ?
C17A C7A C6A 116.09(10) . . ?
C8A C7A C6A 104.59(10) . . ?
C17A C7A H7AA 106.9 . . ?
C8A C7A H7AA 106.9 . . ?
C6A C7A H7AA 106.9 . . ?
N6A C8A C7A 103.12(10) . . ?
N6A C8A H8AA 111.1 . . ?
C7A C8A H8AA 111.1 . . ?
N6A C8A H8AB 111.1 . . ?
C7A C8A H8AB 111.1 . . ?
H8AA C8A H8AB 109.1 . . ?
N6A C9A C16A 112.16(10) . . ?
N6A C9A C10A 112.85(10) . . ?
C16A C9A C10A 101.60(10) . . ?
N6A C9A C6A 103.00(9) . . ?
C16A C9A C6A 119.62(10) . . ?
C10A C9A C6A 107.88(10) . . ?
O3A C10A N7A 126.29(12) . . ?
O3A C10A C9A 125.92(12) . . ?
N7A C10A C9A 107.79(11) . . ?
C12A C11A N7A 127.14(13) . . ?
C12A C11A C16A 122.33(13) . . ?
N7A C11A C16A 110.38(12) . . ?
C11A C12A C13A 117.44(13) . . ?
C11A C12A H12B 121.3 . . ?
C13A C12A H12B 121.3 . . ?
C12A C13A C14A 121.21(13) . . ?
C12A C13A H13B 119.4 . . ?
C14A C13A H13B 119.4 . . ?
C13A C14A C15A 120.69(14) . . ?
C13A C14A H14B 119.7 . . ?
C15A C14A H14B 119.7 . . ?
C16A C15A C14A 118.59(13) . . ?
C16A C15A H15B 120.7 . . ?
C14A C15A H15B 120.7 . . ?
C15A C16A C11A 119.65(12) . . ?
C15A C16A C9A 131.50(12) . . ?
C11A C16A C9A 108.33(11) . . ?
C18A C17A C22A 116.92(14) . . ?
C18A C17A C7A 120.03(14) . . ?
C22A C17A C7A 123.05(14) . . ?
F1A C18A C19A 117.74(16) . . ?
F1A C18A C17A 118.72(14) . . ?
C19A C18A C17A 123.53(18) . . ?
C20A C19A C18A 118.05(19) . . ?
C20A C19A H19B 121.0 . . ?
C18A C19A H19B 121.0 . . ?
C21A C20A C19A 120.62(17) . . ?
C21A C20A H20B 119.7 . . ?
C19A C20A H20B 119.7 . . ?
C20A C21A C22A 120.16(19) . . ?
C20A C21A H21B 119.9 . . ?
C22A C21A H21B 119.9 . . ?
C17A C22A C21A 120.71(18) . . ?
C17A C22A H22B 119.6 . . ?
C21A C22A H22B 119.6 . . ?
N2A C23A C24A 111.71(12) . . ?
N2A C23A H23C 109.3 . . ?
C24A C23A H23C 109.3 . . ?
N2A C23A H23D 109.3 . . ?
C24A C23A H23D 109.3 . . ?
H23C C23A H23D 107.9 . . ?
C23A C24A H24D 109.5 . . ?
C23A C24A H24E 109.5 . . ?
H24D C24A H24E 109.5 . . ?
C23A C24A H24F 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?
N1A C25A C26A 112.30(11) . . ?
N1A C25A H25C 109.1 . . ?
C26A C25A H25C 109.1 . . ?
N1A C25A H25D 109.1 . . ?
C26A C25A H25D 109.1 . . ?
H25C C25A H25D 107.9 . . ?
C25A C26A H26D 109.5 . . ?
C25A C26A H26E 109.5 . . ?
H26D C26A H26E 109.5 . . ?
C25A C26A H26F 109.5 . . ?
H26D C26A H26F 109.5 . . ?
H26E C26A H26F 109.5 . . ?
N6A C27A H27D 109.5 . . ?
N6A C27A H27E 109.5 . . ?
H27D C27A H27E 109.5 . . ?
N6A C27A H27F 109.5 . . ?
H27D C27A H27F 109.5 . . ?
H27E C27A H27F 109.5 . . ?
C1S O1S H1SO 112.5(15) . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
H2SA O2S H2SB 103(2) . . ?

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
C2 N3 N4 C5 155.39(11) . . . . ?
C2 N3 N4 C4 -17.77(15) . . . . ?
C2 N1 C1 O1 170.36(12) . . . . ?
C23 N1 C1 O1 15.3(2) . . . . ?
C2 N1 C1 N2 -8.75(14) . . . . ?
C23 N1 C1 N2 -163.82(11) . . . . ?
C3 N2 C1 O1 169.15(12) . . . . ?
C25 N2 C1 O1 21.50(19) . . . . ?
C3 N2 C1 N1 -11.72(14) . . . . ?
C25 N2 C1 N1 -159.37(11) . . . . ?
N4 N3 C2 N1 -82.51(13) . . . . ?
N4 N3 C2 C3 34.35(14) . . . . ?
C1 N1 C2 N3 149.45(10) . . . . ?
C23 N1 C2 N3 -55.32(15) . . . . ?
C1 N1 C2 C3 23.69(12) . . . . ?
C23 N1 C2 C3 178.92(11) . . . . ?
C1 N2 C3 N5 -94.54(11) . . . . ?
C25 N2 C3 N5 51.65(14) . . . . ?
C1 N2 C3 C2 25.46(12) . . . . ?
C25 N2 C3 C2 171.66(10) . . . . ?
C4 N5 C3 N2 128.81(11) . . . . ?
C4 N5 C3 C2 16.52(15) . . . . ?
N3 C2 C3 N2 -151.52(10) . . . . ?
N1 C2 C3 N2 -28.58(11) . . . . ?
N3 C2 C3 N5 -34.51(14) . . . . ?
N1 C2 C3 N5 88.43(11) . . . . ?
C3 N5 C4 N4 0.25(18) . . . . ?
C3 N5 C4 S1 -177.38(8) . . . . ?
C5 N4 C4 N5 -173.54(12) . . . . ?
N3 N4 C4 N5 -0.19(19) . . . . ?
C5 N4 C4 S1 4.31(14) . . . . ?
N3 N4 C4 S1 177.66(9) . . . . ?
C6 S1 C4 N5 -179.02(11) . . . . ?
C6 S1 C4 N4 3.00(9) . . . . ?
C4 N4 C5 O2 170.60(12) . . . . ?
N3 N4 C5 O2 -2.81(18) . . . . ?
C4 N4 C5 C6 -11.08(15) . . . . ?
N3 N4 C5 C6 175.52(10) . . . . ?
O2 C5 C6 C7 -46.13(16) . . . . ?
N4 C5 C6 C7 135.56(10) . . . . ?
O2 C5 C6 C9 68.61(15) . . . . ?
N4 C5 C6 C9 -109.70(11) . . . . ?
O2 C5 C6 S1 -169.72(11) . . . . ?
N4 C5 C6 S1 11.97(12) . . . . ?
C4 S1 C6 C5 -8.27(9) . . . . ?
C4 S1 C6 C7 -129.44(9) . . . . ?
C4 S1 C6 C9 113.16(9) . . . . ?
C5 C6 C7 C17 -98.39(12) . . . . ?
C9 C6 C7 C17 141.95(11) . . . . ?
S1 C6 C7 C17 19.86(14) . . . . ?
C5 C6 C7 C8 132.79(10) . . . . ?
C9 C6 C7 C8 13.14(12) . . . . ?
S1 C6 C7 C8 -108.95(10) . . . . ?
C9 N6 C8 C7 46.39(12) . . . . ?
C27 N6 C8 C7 173.88(10) . . . . ?
C17 C7 C8 N6 -163.45(11) . . . . ?
C6 C7 C8 N6 -35.04(12) . . . . ?
C8 N6 C9 C16 -164.33(11) . . . . ?
C27 N6 C9 C16 68.75(14) . . . . ?
C8 N6 C9 C10 79.68(13) . . . . ?
C27 N6 C9 C10 -47.24(15) . . . . ?
C8 N6 C9 C6 -37.09(12) . . . . ?
C27 N6 C9 C6 -164.01(11) . . . . ?
C5 C6 C9 N6 -105.53(11) . . . . ?
C7 C6 C9 N6 13.29(12) . . . . ?
S1 C6 C9 N6 136.80(9) . . . . ?
C5 C6 C9 C16 19.74(14) . . . . ?
C7 C6 C9 C16 138.56(11) . . . . ?
S1 C6 C9 C16 -97.93(11) . . . . ?
C5 C6 C9 C10 133.05(10) . . . . ?
C7 C6 C9 C10 -108.13(11) . . . . ?
S1 C6 C9 C10 15.38(12) . . . . ?
C11 N7 C10 O3 174.98(13) . . . . ?
C11 N7 C10 C9 -5.55(14) . . . . ?
N6 C9 C10 O3 -50.35(17) . . . . ?
C16 C9 C10 O3 -173.23(12) . . . . ?
C6 C9 C10 O3 63.56(16) . . . . ?
N6 C9 C10 N7 130.18(11) . . . . ?
C16 C9 C10 N7 7.31(13) . . . . ?
C6 C9 C10 N7 -115.91(11) . . . . ?
C10 N7 C11 C12 -175.62(14) . . . . ?
C10 N7 C11 C16 1.23(16) . . . . ?
C16 C11 C12 C13 -1.5(2) . . . . ?
N7 C11 C12 C13 175.02(14) . . . . ?
C11 C12 C13 C14 -2.0(2) . . . . ?
C12 C13 C14 C15 2.7(2) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C14 C15 C16 C11 -3.7(2) . . . . ?
C14 C15 C16 C9 -179.33(13) . . . . ?
C12 C11 C16 C15 4.4(2) . . . . ?
N7 C11 C16 C15 -172.69(12) . . . . ?
C12 C11 C16 C9 -179.06(12) . . . . ?
N7 C11 C16 C9 3.86(15) . . . . ?
N6 C9 C16 C15 45.98(19) . . . . ?
C10 C9 C16 C15 169.43(14) . . . . ?
C6 C9 C16 C15 -73.68(18) . . . . ?
N6 C9 C16 C11 -130.04(12) . . . . ?
C10 C9 C16 C11 -6.59(13) . . . . ?
C6 C9 C16 C11 110.29(12) . . . . ?
C8 C7 C17 C18 -147.25(13) . . . . ?
C6 C7 C17 C18 90.18(16) . . . . ?
C8 C7 C17 C22 33.01(19) . . . . ?
C6 C7 C17 C22 -89.56(16) . . . . ?
C22 C17 C18 F1 -179.49(15) . . . . ?
C7 C17 C18 F1 0.8(2) . . . . ?
C22 C17 C18 C19 0.7(2) . . . . ?
C7 C17 C18 C19 -179.09(15) . . . . ?
F1 C18 C19 C20 178.79(16) . . . . ?
C17 C18 C19 C20 -1.4(3) . . . . ?
C18 C19 C20 C21 1.1(3) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C18 C17 C22 C21 0.3(2) . . . . ?
C7 C17 C22 C21 -179.95(14) . . . . ?
C20 C21 C22 C17 -0.5(3) . . . . ?
C1 N1 C23 C24 -107.69(14) . . . . ?
C2 N1 C23 C24 100.33(14) . . . . ?
C1 N2 C25 C26 -170.69(11) . . . . ?
C3 N2 C25 C26 46.12(16) . . . . ?
C2A N3A N4A C5A -158.40(11) . . . . ?
C2A N3A N4A C4A 26.38(15) . . . . ?
C3A N2A C1A O1A -169.46(12) . . . . ?
C23A N2A C1A O1A -14.2(2) . . . . ?
C3A N2A C1A N1A 11.36(14) . . . . ?
C23A N2A C1A N1A 166.59(11) . . . . ?
C2A N1A C1A O1A -170.96(12) . . . . ?
C25A N1A C1A O1A -19.8(2) . . . . ?
C2A N1A C1A N2A 8.22(14) . . . . ?
C25A N1A C1A N2A 159.36(11) . . . . ?
C1A N1A C2A N3A -147.56(11) . . . . ?
C25A N1A C2A N3A 60.81(15) . . . . ?
C1A N1A C2A C3A -22.66(13) . . . . ?
C25A N1A C2A C3A -174.29(11) . . . . ?
N4A N3A C2A N1A 76.92(13) . . . . ?
N4A N3A C2A C3A -40.13(14) . . . . ?
C1A N2A C3A N5A 96.62(12) . . . . ?
C23A N2A C3A N5A -58.16(15) . . . . ?
C1A N2A C3A C2A -24.41(13) . . . . ?
C23A N2A C3A C2A -179.19(11) . . . . ?
C4A N5A C3A N2A -121.92(12) . . . . ?
C4A N5A C3A C2A -9.60(16) . . . . ?
N1A C2A C3A N2A 27.27(11) . . . . ?
N3A C2A C3A N2A 150.12(10) . . . . ?
N1A C2A C3A N5A -89.64(12) . . . . ?
N3A C2A C3A N5A 33.20(15) . . . . ?
C3A N5A C4A N4A -5.65(19) . . . . ?
C3A N5A C4A S1A 172.55(9) . . . . ?
C5A N4A C4A N5A -178.33(12) . . . . ?
N3A N4A C4A N5A -3.00(19) . . . . ?
C5A N4A C4A S1A 3.28(14) . . . . ?
N3A N4A C4A S1A 178.61(9) . . . . ?
C6A S1A C4A N5A 179.75(11) . . . . ?
C6A S1A C4A N4A -1.78(9) . . . . ?
C4A N4A C5A O2A 178.08(12) . . . . ?
N3A N4A C5A O2A 2.74(19) . . . . ?
C4A N4A C5A C6A -3.23(15) . . . . ?
N3A N4A C5A C6A -178.57(10) . . . . ?
O2A C5A C6A C9A -57.58(16) . . . . ?
N4A C5A C6A C9A 123.72(11) . . . . ?
O2A C5A C6A C7A 56.11(15) . . . . ?
N4A C5A C6A C7A -122.60(11) . . . . ?
O2A C5A C6A S1A -179.71(11) . . . . ?
N4A C5A C6A S1A 1.58(12) . . . . ?
C4A S1A C6A C5A 0.14(9) . . . . ?
C4A S1A C6A C9A -122.77(9) . . . . ?
C4A S1A C6A C7A 118.91(9) . . . . ?
C5A C6A C7A C17A 106.92(12) . . . . ?
C9A C6A C7A C17A -133.40(11) . . . . ?
S1A C6A C7A C17A -10.80(14) . . . . ?
C5A C6A C7A C8A -125.47(11) . . . . ?
C9A C6A C7A C8A -5.80(12) . . . . ?
S1A C6A C7A C8A 116.80(10) . . . . ?
C27A N6A C8A C7A -171.35(10) . . . . ?
C9A N6A C8A C7A -45.01(12) . . . . ?
C17A C7A C8A N6A 158.14(11) . . . . ?
C6A C7A C8A N6A 29.75(12) . . . . ?
C8A N6A C9A C16A 170.60(10) . . . . ?
C27A N6A C9A C16A -63.90(14) . . . . ?
C8A N6A C9A C10A -75.37(12) . . . . ?
C27A N6A C9A C10A 50.13(14) . . . . ?
C8A N6A C9A C6A 40.68(12) . . . . ?
C27A N6A C9A C6A 166.18(10) . . . . ?
C5A C6A C9A N6A 95.89(11) . . . . ?
C7A C6A C9A N6A -20.08(11) . . . . ?
S1A C6A C9A N6A -145.42(8) . . . . ?
C5A C6A C9A C16A -29.31(15) . . . . ?
C7A C6A C9A C16A -145.28(11) . . . . ?
S1A C6A C9A C16A 89.37(12) . . . . ?
C5A C6A C9A C10A -144.55(10) . . . . ?
C7A C6A C9A C10A 99.48(10) . . . . ?
S1A C6A C9A C10A -25.87(12) . . . . ?
C11A N7A C10A O3A -176.68(13) . . . . ?
C11A N7A C10A C9A 2.95(14) . . . . ?
N6A C9A C10A O3A 56.43(17) . . . . ?
C16A C9A C10A O3A 176.72(13) . . . . ?
C6A C9A C10A O3A -56.67(16) . . . . ?
N6A C9A C10A N7A -123.19(11) . . . . ?
C16A C9A C10A N7A -2.91(13) . . . . ?
C6A C9A C10A N7A 123.70(11) . . . . ?
C10A N7A C11A C12A 173.87(13) . . . . ?
C10A N7A C11A C16A -1.74(15) . . . . ?
N7A C11A C12A C13A -173.18(13) . . . . ?
C16A C11A C12A C13A 1.9(2) . . . . ?
C11A C12A C13A C14A 1.0(2) . . . . ?
C12A C13A C14A C15A -2.3(2) . . . . ?
C13A C14A C15A C16A 0.8(2) . . . . ?
C14A C15A C16A C11A 2.05(19) . . . . ?
C14A C15A C16A C9A 172.77(13) . . . . ?
C12A C11A C16A C15A -3.5(2) . . . . ?
N7A C11A C16A C15A 172.36(12) . . . . ?
C12A C11A C16A C9A -176.18(12) . . . . ?
N7A C11A C16A C9A -0.33(14) . . . . ?
N6A C9A C16A C15A -48.83(18) . . . . ?
C10A C9A C16A C15A -169.61(13) . . . . ?
C6A C9A C16A C15A 71.89(18) . . . . ?
N6A C9A C16A C11A 122.68(11) . . . . ?
C10A C9A C16A C11A 1.90(13) . . . . ?
C6A C9A C16A C11A -116.60(12) . . . . ?
C8A C7A C17A C18A 133.29(14) . . . . ?
C6A C7A C17A C18A -104.34(15) . . . . ?
C8A C7A C17A C22A -46.05(18) . . . . ?
C6A C7A C17A C22A 76.32(16) . . . . ?
C22A C17A C18A F1A 177.52(14) . . . . ?
C7A C17A C18A F1A -1.9(2) . . . . ?
C22A C17A C18A C19A -1.2(2) . . . . ?
C7A C17A C18A C19A 179.45(15) . . . . ?
F1A C18A C19A C20A -177.86(16) . . . . ?
C17A C18A C19A C20A 0.8(3) . . . . ?
C18A C19A C20A C21A 0.4(3) . . . . ?
C19A C20A C21A C22A -1.2(3) . . . . ?
C18A C17A C22A C21A 0.3(2) . . . . ?
C7A C17A C22A C21A 179.65(14) . . . . ?
C20A C21A C22A C17A 0.9(3) . . . . ?
C1A N2A C23A C24A 164.56(13) . . . . ?
C3A N2A C23A C24A -43.41(18) . . . . ?
C1A N1A C25A C26A 111.82(14) . . . . ?
C2A N1A C25A C26A -100.24(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1S H1SO N5 0.83(2) 2.01(2) 2.8334(15) 171(2) .
O2S H2SA N6A 0.83(2) 2.09(2) 2.8931(15) 164(2) .
N3 H3N O2S 0.869(18) 1.958(18) 2.8122(15) 167.0(16) 1_645
N7 H7N O1A 0.87(2) 1.93(2) 2.7895(15) 169.8(18) 1_655
N3A H3NA O1S 0.887(18) 1.942(18) 2.8136(15) 167.1(16) 2_665
N7A H7NA O1 0.87(2) 1.90(2) 2.7394(15) 161(2) 1_565
O2S H2SB O2 0.87(3) 2.42(3) 3.1074(14) 137(2) 2_666

_refine_diff_density_max         0.454
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.056



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kn36
_database_code_depnum_ccdc_archive 'CCDC 1981083'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2020-01-31 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H25 N7 O3 S '
_chemical_formula_sum            'C25 H25 N7 O3 S'
_chemical_formula_weight         503.58

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.7574(4)
_cell_length_b                   16.3229(7)
_cell_length_c                   33.1283(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5276.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    487
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             2112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6864
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53117
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.423
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5767
_reflns_number_gt                5437
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0942P)²+15.2465P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5767
_refine_ls_number_parameters     355
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.2006
_refine_ls_wR_factor_gt          0.1978
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.17763(7) 0.39118(4) 0.10184(2) 0.01876(19) Uani 1 1 d . . . . .
O1 O 0.1620(2) 0.72206(12) 0.02177(7) 0.0243(5) Uani 1 1 d . . . . .
O2 O 0.0368(2) 0.58341(13) 0.15553(7) 0.0282(5) Uani 1 1 d . . . . .
O3 O -0.0742(2) 0.28702(12) 0.09344(7) 0.0263(5) Uani 1 1 d . . . . .
N1 N 0.1870(3) 0.68617(15) 0.08868(8) 0.0229(5) Uani 1 1 d . . . . .
N2 N 0.3377(2) 0.63785(15) 0.04429(8) 0.0229(5) Uani 1 1 d . . . . .
N3 N 0.4746(3) 0.55017(17) 0.08948(10) 0.0306(6) Uani 1 1 d . . . . .
H3N H 0.546(5) 0.549(3) 0.0704(13) 0.042(12) Uiso 1 1 d . . . . .
N4 N 0.4011(3) 0.47610(15) 0.08454(8) 0.0250(5) Uani 1 1 d . . . . .
N5 N 0.2139(2) 0.54726(14) 0.11439(8) 0.0204(5) Uani 1 1 d . . . . .
N6 N -0.1908(3) 0.42096(16) 0.14626(8) 0.0234(5) Uani 1 1 d . . . . .
N7 N -0.1181(3) 0.38384(15) 0.04492(8) 0.0220(5) Uani 1 1 d . . . . .
H7N H -0.133(4) 0.351(2) 0.0257(12) 0.029(10) Uiso 1 1 d . . . . .
C1 C 0.2238(3) 0.68582(16) 0.04888(9) 0.0213(6) Uani 1 1 d . . . . .
C2 C 0.2732(3) 0.63080(17) 0.11152(9) 0.0233(6) Uani 1 1 d . . . . .
H2A H 0.296073 0.653493 0.138741 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4005(3) 0.62564(19) 0.08423(10) 0.0260(6) Uani 1 1 d . . . . .
H3A H 0.462707 0.672750 0.090309 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2789(3) 0.47922(17) 0.09860(9) 0.0199(6) Uani 1 1 d . . . . .
C5 C 0.0948(3) 0.53241(17) 0.13549(9) 0.0213(6) Uani 1 1 d . . . . .
C6 C 0.0471(3) 0.44269(17) 0.13228(8) 0.0175(5) Uani 1 1 d . . . . .
C7 C -0.0984(3) 0.43332(16) 0.11197(8) 0.0165(5) Uani 1 1 d . . . . .
C8 C -0.1161(3) 0.3688(2) 0.17488(10) 0.0267(6) Uani 1 1 d . . . . .
H8A H -0.109852 0.311724 0.164958 0.032 Uiso 1 1 calc R U . . .
H8B H -0.160613 0.368949 0.201745 0.032 Uiso 1 1 calc R U . . .
C9 C 0.0248(3) 0.40915(19) 0.17652(9) 0.0227(6) Uani 1 1 d . . . . .
H9A H 0.019187 0.457149 0.195209 0.027 Uiso 1 1 calc R U . A 1
C10 C -0.0938(3) 0.35766(17) 0.08299(9) 0.0201(6) Uani 1 1 d . . . . .
C11 C -0.1463(3) 0.46828(17) 0.04405(9) 0.0194(6) Uani 1 1 d . . . . .
C12 C -0.1796(3) 0.51571(19) 0.01087(10) 0.0250(6) Uani 1 1 d . . . . .
H12A H -0.180100 0.493190 -0.015571 0.030 Uiso 1 1 calc R U . . .
C13 C -0.2121(3) 0.59735(19) 0.01756(10) 0.0279(7) Uani 1 1 d . . . . .
H13A H -0.233696 0.631563 -0.004754 0.033 Uiso 1 1 calc R U . . .
C14 C -0.2137(3) 0.62963(18) 0.05594(11) 0.0275(7) Uani 1 1 d . . . . .
H14A H -0.238899 0.685281 0.059858 0.033 Uiso 1 1 calc R U . . .
C15 C -0.1785(3) 0.58111(18) 0.08932(10) 0.0235(6) Uani 1 1 d . . . . .
H15A H -0.180218 0.603223 0.115843 0.028 Uiso 1 1 calc R U . . .
C16 C -0.1411(3) 0.50043(16) 0.08284(9) 0.0174(5) Uani 1 1 d . . . . .
C17 C 0.0771(3) 0.73720(19) 0.10461(10) 0.0277(7) Uani 1 1 d . . . . .
H17A H 0.061393 0.783568 0.086398 0.042 Uiso 1 1 calc R U . . .
H17B H 0.102874 0.757684 0.131360 0.042 Uiso 1 1 calc R U . . .
H17C H -0.007020 0.704663 0.106795 0.042 Uiso 1 1 calc R U . . .
C18 C 0.4258(3) 0.6463(2) 0.00923(11) 0.0333(7) Uani 1 1 d . . . . .
H18A H 0.372278 0.667395 -0.013538 0.050 Uiso 1 1 calc R U . . .
H18B H 0.464200 0.592695 0.002143 0.050 Uiso 1 1 calc R U . . .
H18C H 0.500457 0.684445 0.015406 0.050 Uiso 1 1 calc R U . . .
C19 C -0.3254(3) 0.3881(2) 0.13535(11) 0.0324(7) Uani 1 1 d . . . . .
H19A H -0.365479 0.421581 0.113804 0.049 Uiso 1 1 calc R U . . .
H19B H -0.385634 0.389264 0.159024 0.049 Uiso 1 1 calc R U . . .
H19C H -0.315334 0.331532 0.125923 0.049 Uiso 1 1 calc R U . . .
C20 C 0.143(2) 0.3504(7) 0.1923(6) 0.0211(16) Uani 0.493(8) 1 d . U P B 1
C21 C 0.2646(16) 0.3901(6) 0.2015(4) 0.0281(15) Uani 0.493(8) 1 d . U P B 1
H21A H 0.272731 0.447691 0.198281 0.034 Uiso 0.493(8) 1 calc R U P B 1
C22 C 0.3767(10) 0.3432(7) 0.2160(3) 0.0282(13) Uani 0.493(8) 1 d . U P B 1
H22A H 0.461294 0.369148 0.222134 0.034 Uiso 0.493(8) 1 calc R U P B 1
C23 C 0.3623(9) 0.2598(6) 0.2211(2) 0.0267(13) Uani 0.493(8) 1 d . U P B 1
H23A H 0.437488 0.228078 0.230489 0.032 Uiso 0.493(8) 1 calc R U P B 1
C24 C 0.2380(10) 0.2223(6) 0.2126(3) 0.0308(14) Uani 0.493(8) 1 d . U P B 1
H24A H 0.228104 0.164967 0.216570 0.037 Uiso 0.493(8) 1 calc R U P B 1
C25 C 0.1279(13) 0.2677(8) 0.1982(5) 0.0268(17) Uani 0.493(8) 1 d . U P B 1
H25A H 0.042898 0.241715 0.192559 0.032 Uiso 0.493(8) 1 calc R U P B 1
C20' C 0.146(2) 0.3698(7) 0.1936(6) 0.0211(16) Uani 0.507(8) 1 d . U P B 2
C21' C 0.2620(15) 0.4142(6) 0.2042(4) 0.0281(15) Uani 0.507(8) 1 d . U P B 2
H21B H 0.258506 0.472280 0.202874 0.034 Uiso 0.507(8) 1 calc R U P B 2
C22' C 0.3824(9) 0.3772(6) 0.2167(3) 0.0282(13) Uani 0.507(8) 1 d . U P B 2
H22B H 0.460071 0.409510 0.223460 0.034 Uiso 0.507(8) 1 calc R U P B 2
C23' C 0.3883(9) 0.2929(7) 0.2192(2) 0.0267(13) Uani 0.507(8) 1 d . U P B 2
H23B H 0.471071 0.267393 0.227605 0.032 Uiso 0.507(8) 1 calc R U P B 2
C24' C 0.2781(10) 0.2456(6) 0.2100(3) 0.0308(14) Uani 0.507(8) 1 d . U P B 2
H24B H 0.283250 0.187649 0.212480 0.037 Uiso 0.507(8) 1 calc R U P B 2
C25' C 0.1543(13) 0.2837(8) 0.1965(5) 0.0268(17) Uani 0.507(8) 1 d . U P B 2
H25B H 0.077352 0.251024 0.189487 0.032 Uiso 0.507(8) 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C4 1.747(3) . ?
S1 C6 1.829(3) . ?
O1 C1 1.233(4) . ?
O2 C5 1.206(4) . ?
O3 C10 1.219(3) . ?
N1 C1 1.366(4) . ?
N1 C2 1.448(4) . ?
N1 C17 1.457(4) . ?
N2 C1 1.368(4) . ?
N2 C18 1.452(4) . ?
N2 C3 1.472(4) . ?
N3 N4 1.415(4) . ?
N3 C3 1.439(4) . ?
N3 H3N 0.94(5) . ?
N4 C4 1.281(4) . ?
N5 C5 1.378(4) . ?
N5 C4 1.382(4) . ?
N5 C2 1.484(3) . ?
N6 C19 1.465(4) . ?
N6 C7 1.464(4) . ?
N6 C8 1.468(4) . ?
N7 C10 1.352(4) . ?
N7 C11 1.406(4) . ?
N7 H7N 0.85(4) . ?
C2 C3 1.539(4) . ?
C2 H2A 1.0000 . ?
C3 H3A 1.0000 . ?
C5 C6 1.540(4) . ?
C6 C7 1.578(4) . ?
C6 C9 1.580(4) . ?
C7 C16 1.518(4) . ?
C7 C10 1.565(4) . ?
C8 C9 1.526(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C20' 1.462(19) . ?
C9 C20 1.586(18) . ?
C9 H9A 1.0000 . ?
C11 C12 1.383(4) . ?
C11 C16 1.389(4) . ?
C12 C13 1.388(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.376(5) . ?
C13 H13A 0.9500 . ?
C14 C15 1.403(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.383(4) . ?
C15 H15A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.371(16) . ?
C20 C21 1.39(2) . ?
C21 C22 1.418(17) . ?
C21 H21A 0.9500 . ?
C22 C23 1.379(11) . ?
C22 H22A 0.9500 . ?
C23 C24 1.388(11) . ?
C23 H23A 0.9500 . ?
C24 C25 1.390(17) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
C20' C21' 1.39(2) . ?
C20' C25' 1.410(16) . ?
C21' C22' 1.383(16) . ?
C21' H21B 0.9500 . ?
C22' C23' 1.381(10) . ?
C22' H22B 0.9500 . ?
C23' C24' 1.358(11) . ?
C23' H23B 0.9500 . ?
C24' C25' 1.431(16) . ?
C24' H24B 0.9500 . ?
C25' H25B 0.9500 . ?

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
C4 S1 C6 92.85(13) . . ?
C1 N1 C2 110.4(2) . . ?
C1 N1 C17 123.0(3) . . ?
C2 N1 C17 126.5(3) . . ?
C1 N2 C18 121.1(3) . . ?
C1 N2 C3 108.4(2) . . ?
C18 N2 C3 119.0(2) . . ?
N4 N3 C3 117.6(2) . . ?
N4 N3 H3N 106(3) . . ?
C3 N3 H3N 108(3) . . ?
C4 N4 N3 113.3(3) . . ?
C5 N5 C4 116.0(2) . . ?
C5 N5 C2 121.5(2) . . ?
C4 N5 C2 122.4(2) . . ?
C19 N6 C7 114.3(2) . . ?
C19 N6 C8 113.1(2) . . ?
C7 N6 C8 106.0(2) . . ?
C10 N7 C11 111.3(2) . . ?
C10 N7 H7N 122(3) . . ?
C11 N7 H7N 125(3) . . ?
O1 C1 N1 124.9(3) . . ?
O1 C1 N2 126.2(3) . . ?
N1 C1 N2 108.8(2) . . ?
N1 C2 N5 112.4(2) . . ?
N1 C2 C3 101.3(2) . . ?
N5 C2 C3 107.6(2) . . ?
N1 C2 H2A 111.7 . . ?
N5 C2 H2A 111.7 . . ?
C3 C2 H2A 111.7 . . ?
N3 C3 N2 115.7(3) . . ?
N3 C3 C2 112.4(3) . . ?
N2 C3 C2 100.6(2) . . ?
N3 C3 H3A 109.2 . . ?
N2 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
N4 C4 N5 126.6(3) . . ?
N4 C4 S1 121.1(2) . . ?
N5 C4 S1 112.2(2) . . ?
O2 C5 N5 123.6(3) . . ?
O2 C5 C6 123.5(3) . . ?
N5 C5 C6 112.8(2) . . ?
C5 C6 C7 113.2(2) . . ?
C5 C6 C9 107.9(2) . . ?
C7 C6 C9 103.8(2) . . ?
C5 C6 S1 105.34(19) . . ?
C7 C6 S1 110.30(18) . . ?
C9 C6 S1 116.60(19) . . ?
N6 C7 C16 115.1(2) . . ?
N6 C7 C10 112.6(2) . . ?
C16 C7 C10 100.8(2) . . ?
N6 C7 C6 103.7(2) . . ?
C16 C7 C6 116.6(2) . . ?
C10 C7 C6 108.2(2) . . ?
N6 C8 C9 102.7(2) . . ?
N6 C8 H8A 111.2 . . ?
C9 C8 H8A 111.2 . . ?
N6 C8 H8B 111.2 . . ?
C9 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C20' C9 C8 123.7(6) . . ?
C8 C9 C20 113.9(6) . . ?
C20' C9 C6 113.6(8) . . ?
C8 C9 C6 103.9(2) . . ?
C20 C9 C6 114.5(7) . . ?
C8 C9 H9A 108.1 . . ?
C20 C9 H9A 108.1 . . ?
C6 C9 H9A 108.1 . . ?
O3 C10 N7 126.3(3) . . ?
O3 C10 C7 125.2(3) . . ?
N7 C10 C7 108.5(2) . . ?
C12 C11 C16 122.2(3) . . ?
C12 C11 N7 127.7(3) . . ?
C16 C11 N7 110.1(2) . . ?
C11 C12 C13 117.7(3) . . ?
C11 C12 H12A 121.2 . . ?
C13 C12 H12A 121.2 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C16 C15 C14 118.7(3) . . ?
C16 C15 H15A 120.7 . . ?
C14 C15 H15A 120.7 . . ?
C15 C16 C11 119.6(3) . . ?
C15 C16 C7 131.3(3) . . ?
C11 C16 C7 109.0(2) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N6 C19 H19A 109.5 . . ?
N6 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N6 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 121.2(15) . . ?
C25 C20 C9 124.4(14) . . ?
C21 C20 C9 114.3(9) . . ?
C22 C21 C20 118.9(10) . . ?
C22 C21 H21A 120.5 . . ?
C20 C21 H21A 120.5 . . ?
C21 C22 C23 119.7(9) . . ?
C21 C22 H22A 120.1 . . ?
C23 C22 H22A 120.1 . . ?
C24 C23 C22 119.9(8) . . ?
C24 C23 H23A 120.0 . . ?
C22 C23 H23A 120.0 . . ?
C23 C24 C25 120.7(8) . . ?
C23 C24 H24A 119.7 . . ?
C25 C24 H24A 119.7 . . ?
C20 C25 C24 119.5(12) . . ?
C20 C25 H25A 120.3 . . ?
C24 C25 H25A 120.3 . . ?
C21' C20' C25' 117.2(14) . . ?
C21' C20' C9 121.9(9) . . ?
C25' C20' C9 120.6(13) . . ?
C20' C21' C22' 122.6(9) . . ?
C20' C21' H21B 118.7 . . ?
C22' C21' H21B 118.7 . . ?
C23' C22' C21' 119.2(8) . . ?
C23' C22' H22B 120.4 . . ?
C21' C22' H22B 120.4 . . ?
C24' C23' C22' 121.4(8) . . ?
C24' C23' H23B 119.3 . . ?
C22' C23' H23B 119.3 . . ?
C23' C24' C25' 119.4(8) . . ?
C23' C24' H24B 120.3 . . ?
C25' C24' H24B 120.3 . . ?
C20' C25' C24' 120.1(12) . . ?
C20' C25' H25B 119.9 . . ?
C24' C25' H25B 119.9 . . ?

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
_geom_torsion_publ_flag
C3 N3 N4 C4 -38.1(4) . . . . ?
C2 N1 C1 O1 174.1(3) . . . . ?
C17 N1 C1 O1 -6.8(4) . . . . ?
C2 N1 C1 N2 -4.8(3) . . . . ?
C17 N1 C1 N2 174.3(2) . . . . ?
C18 N2 C1 O1 21.4(4) . . . . ?
C3 N2 C1 O1 164.3(3) . . . . ?
C18 N2 C1 N1 -159.7(3) . . . . ?
C3 N2 C1 N1 -16.8(3) . . . . ?
C1 N1 C2 N5 -91.8(3) . . . . ?
C17 N1 C2 N5 89.1(3) . . . . ?
C1 N1 C2 C3 22.7(3) . . . . ?
C17 N1 C2 C3 -156.3(3) . . . . ?
C5 N5 C2 N1 -66.6(4) . . . . ?
C4 N5 C2 N1 118.0(3) . . . . ?
C5 N5 C2 C3 -177.2(2) . . . . ?
C4 N5 C2 C3 7.4(4) . . . . ?
N4 N3 C3 N2 -59.9(4) . . . . ?
N4 N3 C3 C2 54.9(4) . . . . ?
C1 N2 C3 N3 151.0(3) . . . . ?
C18 N2 C3 N3 -65.2(4) . . . . ?
C1 N2 C3 C2 29.6(3) . . . . ?
C18 N2 C3 C2 173.4(3) . . . . ?
N1 C2 C3 N3 -154.0(2) . . . . ?
N5 C2 C3 N3 -35.9(3) . . . . ?
N1 C2 C3 N2 -30.3(3) . . . . ?
N5 C2 C3 N2 87.8(3) . . . . ?
N3 N4 C4 N5 5.2(4) . . . . ?
N3 N4 C4 S1 -171.4(2) . . . . ?
C5 N5 C4 N4 -166.4(3) . . . . ?
C2 N5 C4 N4 9.2(4) . . . . ?
C5 N5 C4 S1 10.4(3) . . . . ?
C2 N5 C4 S1 -173.9(2) . . . . ?
C6 S1 C4 N4 169.5(3) . . . . ?
C6 S1 C4 N5 -7.6(2) . . . . ?
C4 N5 C5 O2 169.6(3) . . . . ?
C2 N5 C5 O2 -6.1(4) . . . . ?
C4 N5 C5 C6 -7.9(3) . . . . ?
C2 N5 C5 C6 176.4(2) . . . . ?
O2 C5 C6 C7 63.8(4) . . . . ?
N5 C5 C6 C7 -118.7(3) . . . . ?
O2 C5 C6 C9 -50.4(4) . . . . ?
N5 C5 C6 C9 127.1(2) . . . . ?
O2 C5 C6 S1 -175.6(2) . . . . ?
N5 C5 C6 S1 1.9(3) . . . . ?
C4 S1 C6 C5 3.12(19) . . . . ?
C4 S1 C6 C7 125.57(19) . . . . ?
C4 S1 C6 C9 -116.4(2) . . . . ?
C19 N6 C7 C16 67.7(3) . . . . ?
C8 N6 C7 C16 -167.0(2) . . . . ?
C19 N6 C7 C10 -47.1(3) . . . . ?
C8 N6 C7 C10 78.2(3) . . . . ?
C19 N6 C7 C6 -163.8(2) . . . . ?
C8 N6 C7 C6 -38.5(3) . . . . ?
C5 C6 C7 N6 -101.0(3) . . . . ?
C9 C6 C7 N6 15.7(3) . . . . ?
S1 C6 C7 N6 141.28(18) . . . . ?
C5 C6 C7 C16 26.5(3) . . . . ?
C9 C6 C7 C16 143.2(2) . . . . ?
S1 C6 C7 C16 -91.2(2) . . . . ?
C5 C6 C7 C10 139.2(2) . . . . ?
C9 C6 C7 C10 -104.1(2) . . . . ?
S1 C6 C7 C10 21.5(3) . . . . ?
C19 N6 C8 C9 172.3(3) . . . . ?
C7 N6 C8 C9 46.3(3) . . . . ?
N6 C8 C9 C20' -165.3(9) . . . . ?
N6 C8 C9 C20 -159.2(8) . . . . ?
N6 C8 C9 C6 -34.0(3) . . . . ?
C5 C6 C9 C20' -91.6(6) . . . . ?
C7 C6 C9 C20' 148.1(6) . . . . ?
S1 C6 C9 C20' 26.6(6) . . . . ?
C5 C6 C9 C8 131.4(2) . . . . ?
C7 C6 C9 C8 11.1(3) . . . . ?
S1 C6 C9 C8 -110.4(2) . . . . ?
C5 C6 C9 C20 -103.7(6) . . . . ?
C7 C6 C9 C20 135.9(6) . . . . ?
S1 C6 C9 C20 14.4(7) . . . . ?
C11 N7 C10 O3 175.6(3) . . . . ?
C11 N7 C10 C7 -3.1(3) . . . . ?
N6 C7 C10 O3 -50.8(4) . . . . ?
C16 C7 C10 O3 -174.0(3) . . . . ?
C6 C7 C10 O3 63.1(3) . . . . ?
N6 C7 C10 N7 127.8(3) . . . . ?
C16 C7 C10 N7 4.7(3) . . . . ?
C6 C7 C10 N7 -118.2(2) . . . . ?
C10 N7 C11 C12 -178.0(3) . . . . ?
C10 N7 C11 C16 -0.1(3) . . . . ?
C16 C11 C12 C13 -1.9(4) . . . . ?
N7 C11 C12 C13 175.9(3) . . . . ?
C11 C12 C13 C14 -1.2(5) . . . . ?
C12 C13 C14 C15 1.8(5) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C14 C15 C16 C11 -3.4(4) . . . . ?
C14 C15 C16 C7 -179.9(3) . . . . ?
C12 C11 C16 C15 4.2(4) . . . . ?
N7 C11 C16 C15 -173.9(3) . . . . ?
C12 C11 C16 C7 -178.6(3) . . . . ?
N7 C11 C16 C7 3.3(3) . . . . ?
N6 C7 C16 C15 50.6(4) . . . . ?
C10 C7 C16 C15 172.1(3) . . . . ?
C6 C7 C16 C15 -71.1(4) . . . . ?
N6 C7 C16 C11 -126.2(3) . . . . ?
C10 C7 C16 C11 -4.7(3) . . . . ?
C6 C7 C16 C11 112.1(3) . . . . ?
C8 C9 C20 C25 10(2) . . . . ?
C6 C9 C20 C25 -109.8(16) . . . . ?
C8 C9 C20 C21 -167.8(11) . . . . ?
C6 C9 C20 C21 72.9(14) . . . . ?
C25 C20 C21 C22 2(2) . . . . ?
C9 C20 C21 C22 179.8(11) . . . . ?
C20 C21 C22 C23 -1.0(19) . . . . ?
C21 C22 C23 C24 -0.7(14) . . . . ?
C22 C23 C24 C25 1.1(15) . . . . ?
C21 C20 C25 C24 -2(3) . . . . ?
C9 C20 C25 C24 -179.3(13) . . . . ?
C23 C24 C25 C20 0(2) . . . . ?
C8 C9 C20' C21' -162.9(12) . . . . ?
C6 C9 C20' C21' 69.8(16) . . . . ?
C8 C9 C20' C25' 23(2) . . . . ?
C6 C9 C20' C25' -104.4(15) . . . . ?
C25' C20' C21' C22' 1(2) . . . . ?
C9 C20' C21' C22' -173.5(12) . . . . ?
C20' C21' C22' C23' -0.7(19) . . . . ?
C21' C22' C23' C24' -0.5(15) . . . . ?
C22' C23' C24' C25' 1.4(15) . . . . ?
C21' C20' C25' C24' 0(2) . . . . ?
C9 C20' C25' C24' 174.6(12) . . . . ?
C23' C24' C25' C20' -1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N7 H7N O1 0.85(4) 1.99(4) 2.838(3) 177(4) 5_565

_refine_diff_density_max         0.445
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.071




####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dv12
_database_code_depnum_ccdc_archive 'CCDC 1981085'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2020-01-31 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H24 F N7 O3 S, C H4 O '
_chemical_formula_sum            'C27 H32 F N7 O5 S'
_chemical_formula_weight         585.65

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   17.9516(12)
_cell_length_b                   16.7643(11)
_cell_length_c                   19.6754(13)
_cell_angle_alpha                90
_cell_angle_beta                 112.9590(10)
_cell_angle_gamma                90
_cell_volume                     5452.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    895
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             2464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.178
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            124818
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.655
_diffrn_reflns_theta_max         30.712
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             16896
_reflns_number_gt                12892
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+3.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         16896
_refine_ls_number_parameters     799
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1372
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.46643(2) 0.27501(2) 0.29345(2) 0.01847(7) Uani 1 1 d . . . . .
F1 F 0.34125(7) 0.42934(6) 0.22051(6) 0.0391(2) Uani 1 1 d . . . . .
O1 O 0.42163(7) 0.47417(7) 0.04740(6) 0.0276(2) Uani 1 1 d . . . . .
O2 O 0.25919(6) 0.25752(7) 0.13171(6) 0.0234(2) Uani 1 1 d . . . . .
O3 O 0.42905(7) 0.17727(7) 0.41274(6) 0.0254(2) Uani 1 1 d . . . . .
N1 N 0.49010(8) 0.35459(8) 0.07890(7) 0.0229(2) Uani 1 1 d . . . . .
N2 N 0.35749(8) 0.35512(7) 0.04833(7) 0.0225(2) Uani 1 1 d . . . . .
N3 N 0.51912(8) 0.21745(8) 0.12449(7) 0.0255(3) Uani 1 1 d . . . . .
H3N H 0.5697(12) 0.2123(12) 0.1172(11) 0.030(5) Uiso 1 1 d . . . . .
N4 N 0.53358(8) 0.23535(8) 0.19861(7) 0.0234(2) Uani 1 1 d . . . . .
N5 N 0.39289(7) 0.26216(7) 0.15090(6) 0.0186(2) Uani 1 1 d . . . . .
N6 N 0.26817(7) 0.16299(7) 0.28111(7) 0.0198(2) Uani 1 1 d . . . . .
N7 N 0.45253(8) 0.07191(8) 0.34968(7) 0.0232(3) Uani 1 1 d . . . . .
H7N H 0.4897(13) 0.0495(12) 0.3841(12) 0.031(5) Uiso 1 1 d . . . . .
C1 C 0.42341(9) 0.40123(9) 0.05723(7) 0.0224(3) Uani 1 1 d . . . . .
C2 C 0.46566(9) 0.27024(9) 0.06993(8) 0.0224(3) Uani 1 1 d . . . . .
H2A H 0.459717 0.251673 0.019776 0.027 Uiso 1 1 calc R U . . .
C3 C 0.38204(9) 0.27496(8) 0.07328(7) 0.0202(3) Uani 1 1 d . . . . .
H3A H 0.344109 0.234825 0.039807 0.024 Uiso 1 1 calc R U . . .
C4 C 0.47001(8) 0.25625(8) 0.20710(7) 0.0188(2) Uani 1 1 d . . . . .
C5 C 0.32993(8) 0.25680(8) 0.17312(7) 0.0178(2) Uani 1 1 d . . . . .
C6 C 0.35962(8) 0.24803(8) 0.25739(7) 0.0160(2) Uani 1 1 d . . . . .
C7 C 0.30301(8) 0.29863(8) 0.28458(8) 0.0189(3) Uani 1 1 d . . . . .
H7A H 0.257873 0.318400 0.239161 0.023 Uiso 1 1 calc R U . . .
C8 C 0.26579(9) 0.23752(9) 0.31967(8) 0.0227(3) Uani 1 1 d . . . . .
H8A H 0.297990 0.232785 0.373367 0.027 Uiso 1 1 calc R U . . .
H8B H 0.209512 0.252126 0.311546 0.027 Uiso 1 1 calc R U . . .
C9 C 0.34874(8) 0.16027(8) 0.27878(7) 0.0161(2) Uani 1 1 d . . . . .
C10 C 0.41540(9) 0.13990(8) 0.35621(7) 0.0193(3) Uani 1 1 d . . . . .
C11 C 0.42367(9) 0.04540(8) 0.27635(8) 0.0202(3) Uani 1 1 d . . . . .
C12 C 0.45079(10) -0.01930(9) 0.24903(9) 0.0269(3) Uani 1 1 d . . . . .
H12A H 0.493196 -0.052433 0.280414 0.032 Uiso 1 1 calc R U . . .
C13 C 0.41348(10) -0.03392(10) 0.17372(9) 0.0286(3) Uani 1 1 d . . . . .
H13A H 0.431103 -0.077653 0.153096 0.034 Uiso 1 1 calc R U . . .
C14 C 0.35117(9) 0.01388(9) 0.12808(8) 0.0249(3) Uani 1 1 d . . . . .
H14A H 0.326485 0.002388 0.076803 0.030 Uiso 1 1 calc R U . . .
C15 C 0.32430(8) 0.07880(9) 0.15675(8) 0.0197(3) Uani 1 1 d . . . . .
H15A H 0.281327 0.111442 0.125499 0.024 Uiso 1 1 calc R U . . .
C16 C 0.36136(8) 0.09477(8) 0.23151(7) 0.0171(2) Uani 1 1 d . . . . .
C17 C 0.34160(9) 0.37143(9) 0.32931(8) 0.0227(3) Uani 1 1 d . . . . .
C18 C 0.35862(10) 0.43615(10) 0.29396(9) 0.0290(3) Uani 1 1 d . . . . .
C19 C 0.39254(12) 0.50640(11) 0.32853(12) 0.0387(4) Uani 1 1 d . . . . .
H19A H 0.403158 0.549110 0.301861 0.046 Uiso 1 1 calc R U . . .
C20 C 0.41058(13) 0.51263(12) 0.40320(13) 0.0462(5) Uani 1 1 d . . . . .
H20A H 0.433736 0.560438 0.428580 0.055 Uiso 1 1 calc R U . . .
C21 C 0.39522(14) 0.44993(14) 0.44128(12) 0.0479(5) Uani 1 1 d . . . . .
H21A H 0.408007 0.454661 0.492728 0.057 Uiso 1 1 calc R U . . .
C22 C 0.36099(11) 0.37965(11) 0.40445(10) 0.0341(4) Uani 1 1 d . . . . .
H22A H 0.350791 0.336767 0.431195 0.041 Uiso 1 1 calc R U . . .
C23 C 0.56388(10) 0.37941(10) 0.07101(9) 0.0297(3) Uani 1 1 d . . . . .
H23A H 0.566760 0.437794 0.071322 0.045 Uiso 1 1 calc R U . . .
H23B H 0.563819 0.359123 0.024271 0.045 Uiso 1 1 calc R U . . .
H23C H 0.610817 0.358057 0.112102 0.045 Uiso 1 1 calc R U . . .
C24 C 0.27830(10) 0.38869(10) 0.03246(10) 0.0309(3) Uani 1 1 d . . . . .
H24A H 0.270411 0.435403 0.000455 0.046 Uiso 1 1 calc R U . . .
H24B H 0.273988 0.404718 0.078690 0.046 Uiso 1 1 calc R U . . .
H24C H 0.236796 0.348698 0.007478 0.046 Uiso 1 1 calc R U . . .
C25 C 0.24807(10) 0.09354(10) 0.31551(9) 0.0277(3) Uani 1 1 d . . . . .
H25A H 0.254101 0.044949 0.290426 0.042 Uiso 1 1 calc R U . . .
H25B H 0.192069 0.097948 0.311484 0.042 Uiso 1 1 calc R U . . .
H25C H 0.284572 0.091121 0.367698 0.042 Uiso 1 1 calc R U . . .
S1A S 0.02911(3) 0.68528(3) 0.21613(3) 0.03811(11) Uani 1 1 d . . . . .
O1A O 0.03826(7) 0.48181(7) 0.44208(6) 0.0297(2) Uani 1 1 d . . . . .
O2A O 0.20459(7) 0.70691(8) 0.40515(8) 0.0402(3) Uani 1 1 d . . . . .
O3A O 0.09977(9) 0.77989(8) 0.11659(8) 0.0426(3) Uani 1 1 d . . . . .
N1A N -0.04183(8) 0.59293(9) 0.39748(9) 0.0330(3) Uani 1 1 d . . . . .
N2A N 0.08949(8) 0.60951(9) 0.45841(9) 0.0318(3) Uani 1 1 d . . . . .
N3A N -0.07969(11) 0.72802(11) 0.35078(13) 0.0531(5) Uani 1 1 d . . . . .
H3NA H -0.1306(17) 0.7239(16) 0.3446(15) 0.058(7) Uiso 1 1 d . . . . .
N4A N -0.07159(9) 0.71363(10) 0.28340(12) 0.0475(5) Uani 1 1 d . . . . .
N5A N 0.06800(9) 0.70082(9) 0.35719(10) 0.0353(3) Uani 1 1 d . . . . .
N6A N 0.24380(8) 0.78403(8) 0.26595(8) 0.0289(3) Uani 1 1 d . . . . .
N7A N 0.06007(9) 0.88112(9) 0.17331(9) 0.0338(3) Uani 1 1 d . . . . .
H7NA H 0.0283(14) 0.9042(15) 0.1304(13) 0.046(6) Uiso 1 1 d . . . . .
C1A C 0.02881(10) 0.55413(10) 0.43342(9) 0.0262(3) Uani 1 1 d . . . . .
C2A C -0.03074(11) 0.67879(11) 0.41156(13) 0.0410(5) Uani 1 1 d . . . . .
H2AA H -0.041316 0.692639 0.456429 0.049 Uiso 1 1 calc R U . . .
C3A C 0.05995(11) 0.68693(11) 0.42864(12) 0.0368(4) Uani 1 1 d . . . . .
H3AA H 0.085580 0.730508 0.464980 0.044 Uiso 1 1 calc R U . . .
C4A C 0.00102(10) 0.70121(10) 0.29043(12) 0.0381(4) Uani 1 1 d . . . . .
C5A C 0.14126(10) 0.70544(10) 0.35142(11) 0.0340(4) Uani 1 1 d . . . . .
C6A C 0.13460(10) 0.70911(10) 0.27181(11) 0.0316(4) Uani 1 1 d . . . . .
C7A C 0.19927(11) 0.65173(10) 0.26159(13) 0.0383(4) Uani 1 1 d . . . . .
H7AA H 0.236459 0.639038 0.313431 0.046 Uiso 1 1 calc R U . A 1
C8A C 0.25001(11) 0.70655(10) 0.23460(12) 0.0352(4) Uani 1 1 d . . . . .
H8AA H 0.306923 0.688318 0.252845 0.042 Uiso 1 1 calc R U . . .
H8AB H 0.227874 0.708839 0.180007 0.042 Uiso 1 1 calc R U . . .
C9A C 0.15894(9) 0.79445(9) 0.25339(10) 0.0272(3) Uani 1 1 d . . . . .
C10A C 0.10313(10) 0.81569(10) 0.17169(10) 0.0321(4) Uani 1 1 d . . . . .
C11A C 0.08084(10) 0.90994(10) 0.24511(10) 0.0302(3) Uani 1 1 d . . . . .
C12A C 0.04984(11) 0.97547(10) 0.26745(12) 0.0371(4) Uani 1 1 d . . . . .
H12B H 0.008173 1.006976 0.232995 0.045 Uiso 1 1 calc R U . . .
C13A C 0.08178(12) 0.99365(11) 0.34213(13) 0.0399(4) Uani 1 1 d . . . . .
H13B H 0.060420 1.037470 0.359335 0.048 Uiso 1 1 calc R U . . .
C14A C 0.14413(12) 0.94926(11) 0.39210(12) 0.0371(4) Uani 1 1 d . . . . .
H14B H 0.165853 0.963692 0.442805 0.044 Uiso 1 1 calc R U . . .
C15A C 0.17532(10) 0.88354(10) 0.36862(10) 0.0317(3) Uani 1 1 d . . . . .
H15B H 0.218931 0.853728 0.402691 0.038 Uiso 1 1 calc R U . . .
C16A C 0.14173(9) 0.86256(9) 0.29503(10) 0.0274(3) Uani 1 1 d . . . . .
C23A C -0.12046(10) 0.55852(12) 0.38073(10) 0.0347(4) Uani 1 1 d . . . . .
H23D H -0.116575 0.500249 0.379851 0.052 Uiso 1 1 calc R U . . .
H23E H -0.157979 0.577508 0.332367 0.052 Uiso 1 1 calc R U . . .
H23F H -0.140380 0.574374 0.418568 0.052 Uiso 1 1 calc R U . . .
C24A C 0.17325(11) 0.58813(13) 0.49896(12) 0.0414(4) Uani 1 1 d . . . . .
H24D H 0.176427 0.544448 0.533086 0.062 Uiso 1 1 calc R U . . .
H24E H 0.202881 0.634444 0.526947 0.062 Uiso 1 1 calc R U . . .
H24F H 0.197232 0.571004 0.464345 0.062 Uiso 1 1 calc R U . . .
C25A C 0.27827(11) 0.84909(10) 0.23817(11) 0.0326(4) Uani 1 1 d . . . . .
H25D H 0.272081 0.899410 0.260774 0.049 Uiso 1 1 calc R U . . .
H25E H 0.249995 0.852721 0.184438 0.049 Uiso 1 1 calc R U . . .
H25F H 0.335841 0.838759 0.250667 0.049 Uiso 1 1 calc R U . . .
O1S O 0.36810(8) 0.69865(9) 0.44276(7) 0.0371(3) Uani 1 1 d . . . . .
H1SO H 0.3109(19) 0.7149(18) 0.4239(16) 0.074(9) Uiso 1 1 d . . . . .
C1S C 0.39228(14) 0.68206(17) 0.51746(12) 0.0538(6) Uani 1 1 d . . . . .
H1SA H 0.361963 0.636044 0.523843 0.081 Uiso 1 1 calc R U . . .
H1SB H 0.381670 0.728482 0.542613 0.081 Uiso 1 1 calc R U . . .
H1SC H 0.450279 0.669944 0.538648 0.081 Uiso 1 1 calc R U . . .
O2S O 0.31871(13) 0.60352(12) 0.03562(10) 0.0670(5) Uani 1 1 d . . . . .
H2SO H 0.348(2) 0.553(2) 0.039(2) 0.113(13) Uiso 1 1 d . . . . .
C2S C 0.3348(2) 0.6281(2) 0.10639(18) 0.0757(9) Uani 1 1 d . . . . .
H2SA H 0.392947 0.638089 0.131944 0.114 Uiso 1 1 calc R U . . .
H2SB H 0.318222 0.586476 0.132567 0.114 Uiso 1 1 calc R U . . .
H2SC H 0.304824 0.677242 0.105259 0.114 Uiso 1 1 calc R U . . .
F1A F 0.1706(5) 0.5250(6) 0.3390(6) 0.0693(19) Uani 0.405(17) 1 d . . P B 1
C17A C 0.1724(8) 0.5796(8) 0.2323(7) 0.0353(19) Uani 0.405(17) 1 d . . P B 1
C18A C 0.1592(7) 0.5132(7) 0.2664(8) 0.038(2) Uani 0.405(17) 1 d . . P B 1
C19A C 0.1340(5) 0.4406(5) 0.2360(8) 0.043(2) Uani 0.405(17) 1 d . . P B 1
H19B H 0.127526 0.397312 0.264267 0.051 Uiso 0.405(17) 1 calc R U P B 1
C20A C 0.1184(7) 0.4325(6) 0.1621(9) 0.056(3) Uani 0.405(17) 1 d . . P B 1
H20B H 0.100008 0.382867 0.138248 0.068 Uiso 0.405(17) 1 calc R U P B 1
C21A C 0.1290(10) 0.4937(8) 0.1241(9) 0.088(4) Uani 0.405(17) 1 d . . P B 1
H21B H 0.117760 0.487276 0.073092 0.106 Uiso 0.405(17) 1 calc R U P B 1
C22A C 0.1566(10) 0.5684(8) 0.1581(8) 0.069(3) Uani 0.405(17) 1 d . . P B 1
H22B H 0.164457 0.611214 0.129865 0.083 Uiso 0.405(17) 1 calc R U P B 1
F1' F 0.1698(3) 0.5059(3) 0.3107(5) 0.0574(16) Uani 0.595(17) 1 d . . P B 2
C17' C 0.1625(5) 0.5778(4) 0.2062(5) 0.0311(14) Uani 0.595(17) 1 d . . P B 2
C18' C 0.1519(5) 0.5073(5) 0.2369(6) 0.0423(17) Uani 0.595(17) 1 d . . P B 2
C19' C 0.1231(4) 0.4377(3) 0.1970(7) 0.0448(18) Uani 0.595(17) 1 d . . P B 2
H19C H 0.118468 0.390046 0.221134 0.054 Uiso 0.595(17) 1 calc R U P B 2
C20' C 0.1014(4) 0.4391(4) 0.1216(7) 0.057(2) Uani 0.595(17) 1 d . . P B 2
H20C H 0.082171 0.392123 0.093219 0.069 Uiso 0.595(17) 1 calc R U P B 2
C21' C 0.1079(5) 0.5093(4) 0.0879(6) 0.065(2) Uani 0.595(17) 1 d . . P B 2
H21C H 0.092614 0.510983 0.035927 0.078 Uiso 0.595(17) 1 calc R U P B 2
C22' C 0.1372(5) 0.5781(5) 0.1304(5) 0.0515(17) Uani 0.595(17) 1 d . . P B 2
H22C H 0.139697 0.626465 0.106219 0.062 Uiso 0.595(17) 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 C4 1.7534(14) . ?
S1 C6 1.8230(13) . ?
F1 C18 1.359(2) . ?
O1 C1 1.2363(18) . ?
O2 C5 1.2121(17) . ?
O3 C10 1.2153(17) . ?
N1 C1 1.352(2) . ?
N1 C23 1.453(2) . ?
N1 C2 1.4706(19) . ?
N2 C1 1.366(2) . ?
N2 C3 1.4397(18) . ?
N2 C24 1.445(2) . ?
N3 N4 1.4102(18) . ?
N3 C2 1.4328(19) . ?
N3 H3N 0.98(2) . ?
N4 C4 1.2656(19) . ?
N5 C5 1.3647(18) . ?
N5 C4 1.3983(18) . ?
N5 C3 1.4780(17) . ?
N6 C25 1.4609(19) . ?
N6 C9 1.4654(17) . ?
N6 C8 1.4711(18) . ?
N7 C10 1.3515(19) . ?
N7 C11 1.4016(18) . ?
N7 H7N 0.83(2) . ?
C2 C3 1.530(2) . ?
C2 H2A 1.0000 . ?
C3 H3A 1.0000 . ?
C5 C6 1.5380(18) . ?
C6 C9 1.5633(19) . ?
C6 C7 1.5692(19) . ?
C7 C17 1.506(2) . ?
C7 C8 1.527(2) . ?
C7 H7A 1.0000 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C16 1.5123(18) . ?
C9 C10 1.5643(19) . ?
C11 C12 1.381(2) . ?
C11 C16 1.3946(19) . ?
C12 C13 1.389(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.384(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.396(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3836(19) . ?
C15 H15A 0.9500 . ?
C17 C18 1.386(2) . ?
C17 C22 1.387(2) . ?
C18 C19 1.377(2) . ?
C19 C20 1.379(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.380(3) . ?
C20 H20A 0.9500 . ?
C21 C22 1.394(3) . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9500 . ?
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 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
S1A C4A 1.743(2) . ?
S1A C6A 1.8241(17) . ?
O1A C1A 1.2269(19) . ?
O2A C5A 1.214(2) . ?
O3A C10A 1.220(2) . ?
N1A C1A 1.353(2) . ?
N1A C23A 1.439(2) . ?
N1A C2A 1.465(2) . ?
N2A C1A 1.368(2) . ?
N2A C3A 1.438(2) . ?
N2A C24A 1.446(2) . ?
N3A N4A 1.410(3) . ?
N3A C2A 1.436(3) . ?
N3A H3NA 0.88(3) . ?
N4A C4A 1.273(2) . ?
N5A C5A 1.366(2) . ?
N5A C4A 1.392(3) . ?
N5A C3A 1.487(3) . ?
N6A C9A 1.456(2) . ?
N6A C8A 1.461(2) . ?
N6A C25A 1.461(2) . ?
N7A C10A 1.349(2) . ?
N7A C11A 1.399(3) . ?
N7A H7NA 0.90(2) . ?
C2A C3A 1.535(2) . ?
C2A H2AA 1.0000 . ?
C3A H3AA 1.0000 . ?
C5A C6A 1.525(3) . ?
C6A C9A 1.579(2) . ?
C6A C7A 1.580(2) . ?
C7A C17A 1.346(13) . ?
C7A C8A 1.528(2) . ?
C7A C17' 1.612(8) . ?
C7A H7AA 1.0000 . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A C16A 1.506(2) . ?
C9A C10A 1.568(2) . ?
C11A C12A 1.379(3) . ?
C11A C16A 1.397(2) . ?
C12A C13A 1.387(3) . ?
C12A H12B 0.9500 . ?
C13A C14A 1.384(3) . ?
C13A H13B 0.9500 . ?
C14A C15A 1.394(3) . ?
C14A H14B 0.9500 . ?
C15A C16A 1.379(3) . ?
C15A H15B 0.9500 . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
C24A H24D 0.9800 . ?
C24A H24E 0.9800 . ?
C24A H24F 0.9800 . ?
C25A H25D 0.9800 . ?
C25A H25E 0.9800 . ?
C25A H25F 0.9800 . ?
O1S C1S 1.389(2) . ?
O1S H1SO 0.99(3) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
O2S C2S 1.370(3) . ?
O2S H2SO 0.98(4) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
F1A C18A 1.374(10) . ?
C17A C18A 1.368(17) . ?
C17A C22A 1.387(11) . ?
C18A C19A 1.354(13) . ?
C19A C20A 1.374(11) . ?
C19A H19B 0.9500 . ?
C20A C21A 1.326(16) . ?
C20A H20B 0.9500 . ?
C21A C22A 1.415(15) . ?
C21A H21B 0.9500 . ?
C22A H22B 0.9500 . ?
F1' C18' 1.360(6) . ?
C17' C18' 1.374(12) . ?
C17' C22' 1.379(7) . ?
C18' C19' 1.388(9) . ?
C19' C20' 1.378(8) . ?
C19' H19C 0.9500 . ?
C20' C21' 1.378(10) . ?
C20' H20C 0.9500 . ?
C21' C22' 1.401(10) . ?
C21' H21C 0.9500 . ?
C22' H22C 0.9500 . ?

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
C4 S1 C6 90.52(6) . . ?
C1 N1 C23 122.17(13) . . ?
C1 N1 C2 109.41(12) . . ?
C23 N1 C2 120.28(13) . . ?
C1 N2 C3 110.47(12) . . ?
C1 N2 C24 122.50(13) . . ?
C3 N2 C24 125.56(13) . . ?
N4 N3 C2 116.27(12) . . ?
N4 N3 H3N 111.4(12) . . ?
C2 N3 H3N 109.5(12) . . ?
C4 N4 N3 112.56(12) . . ?
C5 N5 C4 115.48(11) . . ?
C5 N5 C3 123.29(12) . . ?
C4 N5 C3 121.22(12) . . ?
C25 N6 C9 114.51(12) . . ?
C25 N6 C8 112.08(12) . . ?
C9 N6 C8 105.67(11) . . ?
C10 N7 C11 111.55(12) . . ?
C10 N7 H7N 124.9(14) . . ?
C11 N7 H7N 123.5(14) . . ?
O1 C1 N1 125.94(14) . . ?
O1 C1 N2 124.83(15) . . ?
N1 C1 N2 109.23(13) . . ?
N3 C2 N1 115.01(13) . . ?
N3 C2 C3 112.41(12) . . ?
N1 C2 C3 101.36(11) . . ?
N3 C2 H2A 109.2 . . ?
N1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
N2 C3 N5 112.78(11) . . ?
N2 C3 C2 102.04(11) . . ?
N5 C3 C2 107.51(11) . . ?
N2 C3 H3A 111.4 . . ?
N5 C3 H3A 111.4 . . ?
C2 C3 H3A 111.4 . . ?
N4 C4 N5 125.51(13) . . ?
N4 C4 S1 123.60(11) . . ?
N5 C4 S1 110.75(10) . . ?
O2 C5 N5 124.42(13) . . ?
O2 C5 C6 123.88(12) . . ?
N5 C5 C6 111.69(11) . . ?
C5 C6 C9 110.67(10) . . ?
C5 C6 C7 108.51(11) . . ?
C9 C6 C7 104.56(10) . . ?
C5 C6 S1 105.39(9) . . ?
C9 C6 S1 110.59(9) . . ?
C7 C6 S1 117.13(9) . . ?
C17 C7 C8 117.51(12) . . ?
C17 C7 C6 115.21(11) . . ?
C8 C7 C6 104.31(11) . . ?
C17 C7 H7A 106.3 . . ?
C8 C7 H7A 106.3 . . ?
C6 C7 H7A 106.3 . . ?
N6 C8 C7 103.34(11) . . ?
N6 C8 H8A 111.1 . . ?
C7 C8 H8A 111.1 . . ?
N6 C8 H8B 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
N6 C9 C16 115.36(11) . . ?
N6 C9 C6 101.99(10) . . ?
C16 C9 C6 116.96(11) . . ?
N6 C9 C10 111.45(11) . . ?
C16 C9 C10 101.49(11) . . ?
C6 C9 C10 109.83(10) . . ?
O3 C10 N7 126.21(13) . . ?
O3 C10 C9 125.68(13) . . ?
N7 C10 C9 108.05(12) . . ?
C12 C11 C16 122.51(13) . . ?
C12 C11 N7 127.23(14) . . ?
C16 C11 N7 110.25(12) . . ?
C11 C12 C13 117.21(14) . . ?
C11 C12 H12A 121.4 . . ?
C13 C12 H12A 121.4 . . ?
C14 C13 C12 121.42(14) . . ?
C14 C13 H13A 119.3 . . ?
C12 C13 H13A 119.3 . . ?
C13 C14 C15 120.56(14) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C16 C15 C14 118.81(13) . . ?
C16 C15 H15A 120.6 . . ?
C14 C15 H15A 120.6 . . ?
C15 C16 C11 119.48(13) . . ?
C15 C16 C9 132.00(13) . . ?
C11 C16 C9 108.51(11) . . ?
C18 C17 C22 116.38(15) . . ?
C18 C17 C7 118.84(14) . . ?
C22 C17 C7 124.78(15) . . ?
F1 C18 C19 118.09(16) . . ?
F1 C18 C17 117.63(14) . . ?
C19 C18 C17 124.28(17) . . ?
C18 C19 C20 117.75(18) . . ?
C18 C19 H19A 121.1 . . ?
C20 C19 H19A 121.1 . . ?
C19 C20 C21 120.46(17) . . ?
C19 C20 H20A 119.8 . . ?
C21 C20 H20A 119.8 . . ?
C20 C21 C22 120.17(19) . . ?
C20 C21 H21A 119.9 . . ?
C22 C21 H21A 119.9 . . ?
C17 C22 C21 120.96(18) . . ?
C17 C22 H22A 119.5 . . ?
C21 C22 H22A 119.5 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N6 C25 H25A 109.5 . . ?
N6 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N6 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C4A S1A C6A 92.00(9) . . ?
C1A N1A C23A 124.23(15) . . ?
C1A N1A C2A 110.06(15) . . ?
C23A N1A C2A 119.07(15) . . ?
C1A N2A C3A 110.53(14) . . ?
C1A N2A C24A 122.75(15) . . ?
C3A N2A C24A 125.99(15) . . ?
N4A N3A C2A 115.51(16) . . ?
N4A N3A H3NA 110.0(18) . . ?
C2A N3A H3NA 109.7(18) . . ?
C4A N4A N3A 113.74(19) . . ?
C5A N5A C4A 115.25(17) . . ?
C5A N5A C3A 122.65(16) . . ?
C4A N5A C3A 121.75(15) . . ?
C9A N6A C8A 106.39(13) . . ?
C9A N6A C25A 114.50(13) . . ?
C8A N6A C25A 113.12(14) . . ?
C10A N7A C11A 112.03(15) . . ?
C10A N7A H7NA 119.1(16) . . ?
C11A N7A H7NA 128.2(15) . . ?
O1A C1A N1A 126.73(16) . . ?
O1A C1A N2A 124.96(15) . . ?
N1A C1A N2A 108.30(14) . . ?
N3A C2A N1A 114.4(2) . . ?
N3A C2A C3A 112.55(16) . . ?
N1A C2A C3A 100.55(14) . . ?
N3A C2A H2AA 109.7 . . ?
N1A C2A H2AA 109.7 . . ?
C3A C2A H2AA 109.7 . . ?
N2A C3A N5A 111.73(15) . . ?
N2A C3A C2A 101.55(14) . . ?
N5A C3A C2A 107.04(17) . . ?
N2A C3A H3AA 112.0 . . ?
N5A C3A H3AA 112.0 . . ?
C2A C3A H3AA 112.0 . . ?
N4A C4A N5A 125.0(2) . . ?
N4A C4A S1A 123.56(18) . . ?
N5A C4A S1A 111.39(13) . . ?
O2A C5A N5A 122.28(19) . . ?
O2A C5A C6A 124.43(16) . . ?
N5A C5A C6A 113.29(15) . . ?
C5A C6A C9A 110.76(14) . . ?
C5A C6A C7A 109.82(14) . . ?
C9A C6A C7A 103.87(13) . . ?
C5A C6A S1A 104.78(11) . . ?
C9A C6A S1A 112.09(11) . . ?
C7A C6A S1A 115.63(13) . . ?
C17A C7A C8A 123.7(6) . . ?
C17A C7A C6A 116.3(6) . . ?
C8A C7A C6A 104.20(13) . . ?
C8A C7A C17' 111.7(3) . . ?
C6A C7A C17' 115.3(3) . . ?
C17A C7A H7AA 103.4 . . ?
C8A C7A H7AA 103.4 . . ?
C6A C7A H7AA 103.4 . . ?
N6A C8A C7A 103.54(15) . . ?
N6A C8A H8AA 111.1 . . ?
C7A C8A H8AA 111.1 . . ?
N6A C8A H8AB 111.1 . . ?
C7A C8A H8AB 111.1 . . ?
H8AA C8A H8AB 109.0 . . ?
N6A C9A C16A 114.95(13) . . ?
N6A C9A C10A 114.16(14) . . ?
C16A C9A C10A 101.59(13) . . ?
N6A C9A C6A 102.55(12) . . ?
C16A C9A C6A 115.36(14) . . ?
C10A C9A C6A 108.53(13) . . ?
O3A C10A N7A 126.22(17) . . ?
O3A C10A C9A 126.13(16) . . ?
N7A C10A C9A 107.65(16) . . ?
C12A C11A C16A 122.08(18) . . ?
C12A C11A N7A 127.99(16) . . ?
C16A C11A N7A 109.93(15) . . ?
C11A C12A C13A 117.48(17) . . ?
C11A C12A H12B 121.3 . . ?
C13A C12A H12B 121.3 . . ?
C14A C13A C12A 121.33(18) . . ?
C14A C13A H13B 119.3 . . ?
C12A C13A H13B 119.3 . . ?
C13A C14A C15A 120.53(19) . . ?
C13A C14A H14B 119.7 . . ?
C15A C14A H14B 119.7 . . ?
C16A C15A C14A 118.80(17) . . ?
C16A C15A H15B 120.6 . . ?
C14A C15A H15B 120.6 . . ?
C15A C16A C11A 119.66(16) . . ?
C15A C16A C9A 131.75(15) . . ?
C11A C16A C9A 108.59(15) . . ?
N1A C23A H23D 109.5 . . ?
N1A C23A H23E 109.5 . . ?
H23D C23A H23E 109.5 . . ?
N1A C23A H23F 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
N2A C24A H24D 109.5 . . ?
N2A C24A H24E 109.5 . . ?
H24D C24A H24E 109.5 . . ?
N2A C24A H24F 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?
N6A C25A H25D 109.5 . . ?
N6A C25A H25E 109.5 . . ?
H25D C25A H25E 109.5 . . ?
N6A C25A H25F 109.5 . . ?
H25D C25A H25F 109.5 . . ?
H25E C25A H25F 109.5 . . ?
C1S O1S H1SO 107.6(17) . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C2S O2S H2SO 107(2) . . ?
O2S C2S H2SA 109.5 . . ?
O2S C2S H2SB 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
O2S C2S H2SC 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C7A C17A C18A 128.5(8) . . ?
C7A C17A C22A 117.7(11) . . ?
C18A C17A C22A 113.9(11) . . ?
C19A C18A C17A 127.2(9) . . ?
C19A C18A F1A 118.6(8) . . ?
C17A C18A F1A 114.1(9) . . ?
C18A C19A C20A 116.9(10) . . ?
C18A C19A H19B 121.6 . . ?
C20A C19A H19B 121.6 . . ?
C21A C20A C19A 120.3(9) . . ?
C21A C20A H20B 119.8 . . ?
C19A C20A H20B 119.8 . . ?
C20A C21A C22A 121.3(9) . . ?
C20A C21A H21B 119.4 . . ?
C22A C21A H21B 119.4 . . ?
C17A C22A C21A 120.4(11) . . ?
C17A C22A H22B 119.8 . . ?
C21A C22A H22B 119.8 . . ?
C18' C17' C22' 115.8(6) . . ?
C18' C17' C7A 117.0(5) . . ?
C22' C17' C7A 127.1(6) . . ?
F1' C18' C17' 118.0(7) . . ?
F1' C18' C19' 118.1(7) . . ?
C17' C18' C19' 123.9(6) . . ?
C20' C19' C18' 118.7(6) . . ?
C20' C19' H19C 120.6 . . ?
C18' C19' H19C 120.6 . . ?
C19' C20' C21' 119.4(5) . . ?
C19' C20' H20C 120.3 . . ?
C21' C20' H20C 120.3 . . ?
C20' C21' C22' 119.9(6) . . ?
C20' C21' H21C 120.1 . . ?
C22' C21' H21C 120.1 . . ?
C17' C22' C21' 122.1(7) . . ?
C17' C22' H22C 119.0 . . ?
C21' C22' H22C 119.0 . . ?

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
C2 N3 N4 C4 41.85(18) . . . . ?
C23 N1 C1 O1 -20.2(2) . . . . ?
C2 N1 C1 O1 -168.71(14) . . . . ?
C23 N1 C1 N2 160.39(13) . . . . ?
C2 N1 C1 N2 11.84(15) . . . . ?
C3 N2 C1 O1 -172.58(13) . . . . ?
C24 N2 C1 O1 -5.7(2) . . . . ?
C3 N2 C1 N1 6.88(16) . . . . ?
C24 N2 C1 N1 173.76(13) . . . . ?
N4 N3 C2 N1 57.06(17) . . . . ?
N4 N3 C2 C3 -58.25(17) . . . . ?
C1 N1 C2 N3 -145.55(12) . . . . ?
C23 N1 C2 N3 65.20(17) . . . . ?
C1 N1 C2 C3 -24.03(14) . . . . ?
C23 N1 C2 C3 -173.27(12) . . . . ?
C1 N2 C3 N5 93.71(14) . . . . ?
C24 N2 C3 N5 -72.68(18) . . . . ?
C1 N2 C3 C2 -21.33(14) . . . . ?
C24 N2 C3 C2 172.29(14) . . . . ?
C5 N5 C3 N2 73.15(17) . . . . ?
C4 N5 C3 N2 -105.60(15) . . . . ?
C5 N5 C3 C2 -175.16(12) . . . . ?
C4 N5 C3 C2 6.09(17) . . . . ?
N3 C2 C3 N2 149.50(12) . . . . ?
N1 C2 C3 N2 26.18(13) . . . . ?
N3 C2 C3 N5 30.66(16) . . . . ?
N1 C2 C3 N5 -92.66(12) . . . . ?
N3 N4 C4 N5 -0.3(2) . . . . ?
N3 N4 C4 S1 174.97(10) . . . . ?
C5 N5 C4 N4 156.98(14) . . . . ?
C3 N5 C4 N4 -24.2(2) . . . . ?
C5 N5 C4 S1 -18.80(15) . . . . ?
C3 N5 C4 S1 160.04(10) . . . . ?
C6 S1 C4 N4 -152.77(13) . . . . ?
C6 S1 C4 N5 23.10(10) . . . . ?
C4 N5 C5 O2 -176.97(13) . . . . ?
C3 N5 C5 O2 4.2(2) . . . . ?
C4 N5 C5 C6 1.91(16) . . . . ?
C3 N5 C5 C6 -176.90(12) . . . . ?
O2 C5 C6 C9 73.97(17) . . . . ?
N5 C5 C6 C9 -104.92(13) . . . . ?
O2 C5 C6 C7 -40.22(18) . . . . ?
N5 C5 C6 C7 140.89(12) . . . . ?
O2 C5 C6 S1 -166.45(12) . . . . ?
N5 C5 C6 S1 14.66(13) . . . . ?
C4 S1 C6 C5 -20.76(9) . . . . ?
C4 S1 C6 C9 98.89(9) . . . . ?
C4 S1 C6 C7 -141.49(10) . . . . ?
C5 C6 C7 C17 -110.78(13) . . . . ?
C9 C6 C7 C17 131.08(12) . . . . ?
S1 C6 C7 C17 8.31(16) . . . . ?
C5 C6 C7 C8 118.91(12) . . . . ?
C9 C6 C7 C8 0.77(13) . . . . ?
S1 C6 C7 C8 -122.00(11) . . . . ?
C25 N6 C8 C7 169.99(12) . . . . ?
C9 N6 C8 C7 44.63(14) . . . . ?
C17 C7 C8 N6 -155.27(12) . . . . ?
C6 C7 C8 N6 -26.34(14) . . . . ?
C25 N6 C9 C16 64.95(15) . . . . ?
C8 N6 C9 C16 -171.20(11) . . . . ?
C25 N6 C9 C6 -167.20(11) . . . . ?
C8 N6 C9 C6 -43.36(13) . . . . ?
C25 N6 C9 C10 -50.07(15) . . . . ?
C8 N6 C9 C10 73.77(13) . . . . ?
C5 C6 C9 N6 -91.64(12) . . . . ?
C7 C6 C9 N6 25.02(12) . . . . ?
S1 C6 C9 N6 151.95(9) . . . . ?
C5 C6 C9 C16 35.18(15) . . . . ?
C7 C6 C9 C16 151.84(11) . . . . ?
S1 C6 C9 C16 -81.23(12) . . . . ?
C5 C6 C9 C10 150.07(11) . . . . ?
C7 C6 C9 C10 -93.27(12) . . . . ?
S1 C6 C9 C10 33.66(13) . . . . ?
C11 N7 C10 O3 -178.57(14) . . . . ?
C11 N7 C10 C9 3.98(16) . . . . ?
N6 C9 C10 O3 -57.27(18) . . . . ?
C16 C9 C10 O3 179.40(14) . . . . ?
C6 C9 C10 O3 55.00(18) . . . . ?
N6 C9 C10 N7 120.20(13) . . . . ?
C16 C9 C10 N7 -3.13(14) . . . . ?
C6 C9 C10 N7 -127.53(12) . . . . ?
C10 N7 C11 C12 176.34(15) . . . . ?
C10 N7 C11 C16 -3.26(17) . . . . ?
C16 C11 C12 C13 0.2(2) . . . . ?
N7 C11 C12 C13 -179.32(15) . . . . ?
C11 C12 C13 C14 -0.6(2) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C13 C14 C15 C16 0.4(2) . . . . ?
C14 C15 C16 C11 -0.7(2) . . . . ?
C14 C15 C16 C9 178.08(14) . . . . ?
C12 C11 C16 C15 0.5(2) . . . . ?
N7 C11 C16 C15 -179.92(12) . . . . ?
C12 C11 C16 C9 -178.62(14) . . . . ?
N7 C11 C16 C9 1.00(16) . . . . ?
N6 C9 C16 C15 61.69(19) . . . . ?
C6 C9 C16 C15 -58.2(2) . . . . ?
C10 C9 C16 C15 -177.69(14) . . . . ?
N6 C9 C16 C11 -119.39(13) . . . . ?
C6 C9 C16 C11 120.68(13) . . . . ?
C10 C9 C16 C11 1.23(14) . . . . ?
C8 C7 C17 C18 -164.96(14) . . . . ?
C6 C7 C17 C18 71.45(17) . . . . ?
C8 C7 C17 C22 14.1(2) . . . . ?
C6 C7 C17 C22 -109.44(17) . . . . ?
C22 C17 C18 F1 179.13(15) . . . . ?
C7 C17 C18 F1 -1.7(2) . . . . ?
C22 C17 C18 C19 -0.3(3) . . . . ?
C7 C17 C18 C19 178.91(16) . . . . ?
F1 C18 C19 C20 -179.50(17) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C18 C17 C22 C21 0.4(3) . . . . ?
C7 C17 C22 C21 -178.71(17) . . . . ?
C20 C21 C22 C17 -0.2(3) . . . . ?
C2A N3A N4A C4A -40.8(2) . . . . ?
C23A N1A C1A O1A 17.9(3) . . . . ?
C2A N1A C1A O1A 168.84(17) . . . . ?
C23A N1A C1A N2A -162.79(17) . . . . ?
C2A N1A C1A N2A -11.9(2) . . . . ?
C3A N2A C1A O1A 170.45(16) . . . . ?
C24A N2A C1A O1A -0.3(3) . . . . ?
C3A N2A C1A N1A -8.9(2) . . . . ?
C24A N2A C1A N1A -179.60(17) . . . . ?
N4A N3A C2A N1A -55.3(2) . . . . ?
N4A N3A C2A C3A 58.6(2) . . . . ?
C1A N1A C2A N3A 146.54(16) . . . . ?
C23A N1A C2A N3A -60.8(2) . . . . ?
C1A N1A C2A C3A 25.7(2) . . . . ?
C23A N1A C2A C3A 178.33(16) . . . . ?
C1A N2A C3A N5A -89.61(17) . . . . ?
C24A N2A C3A N5A 80.8(2) . . . . ?
C1A N2A C3A C2A 24.2(2) . . . . ?
C24A N2A C3A C2A -165.45(19) . . . . ?
C5A N5A C3A N2A -65.1(2) . . . . ?
C4A N5A C3A N2A 107.64(18) . . . . ?
C5A N5A C3A C2A -175.48(16) . . . . ?
C4A N5A C3A C2A -2.7(2) . . . . ?
N3A C2A C3A N2A -150.79(19) . . . . ?
N1A C2A C3A N2A -28.6(2) . . . . ?
N3A C2A C3A N5A -33.5(2) . . . . ?
N1A C2A C3A N5A 88.63(17) . . . . ?
N3A N4A C4A N5A 0.4(3) . . . . ?
N3A N4A C4A S1A -177.70(13) . . . . ?
C5A N5A C4A N4A -164.95(17) . . . . ?
C3A N5A C4A N4A 21.8(3) . . . . ?
C5A N5A C4A S1A 13.31(19) . . . . ?
C3A N5A C4A S1A -159.97(13) . . . . ?
C6A S1A C4A N4A 161.38(16) . . . . ?
C6A S1A C4A N5A -16.91(13) . . . . ?
C4A N5A C5A O2A 178.84(16) . . . . ?
C3A N5A C5A O2A -7.9(3) . . . . ?
C4A N5A C5A C6A -0.7(2) . . . . ?
C3A N5A C5A C6A 172.50(15) . . . . ?
O2A C5A C6A C9A -69.7(2) . . . . ?
N5A C5A C6A C9A 109.88(15) . . . . ?
O2A C5A C6A C7A 44.5(2) . . . . ?
N5A C5A C6A C7A -135.97(15) . . . . ?
O2A C5A C6A S1A 169.26(15) . . . . ?
N5A C5A C6A S1A -11.18(17) . . . . ?
C4A S1A C6A C5A 15.35(12) . . . . ?
C4A S1A C6A C9A -104.83(13) . . . . ?
C4A S1A C6A C7A 136.38(14) . . . . ?
C5A C6A C7A C17A 98.5(6) . . . . ?
C9A C6A C7A C17A -143.0(6) . . . . ?
S1A C6A C7A C17A -19.7(6) . . . . ?
C5A C6A C7A C8A -121.74(16) . . . . ?
C9A C6A C7A C8A -3.2(2) . . . . ?
S1A C6A C7A C8A 120.00(15) . . . . ?
C5A C6A C7A C17' 115.5(4) . . . . ?
C9A C6A C7A C17' -126.0(4) . . . . ?
S1A C6A C7A C17' -2.8(4) . . . . ?
C9A N6A C8A C7A -44.85(18) . . . . ?
C25A N6A C8A C7A -171.40(15) . . . . ?
C17A C7A C8A N6A 163.7(7) . . . . ?
C6A C7A C8A N6A 27.8(2) . . . . ?
C17' C7A C8A N6A 152.9(3) . . . . ?
C8A N6A C9A C16A 167.91(14) . . . . ?
C25A N6A C9A C16A -66.37(19) . . . . ?
C8A N6A C9A C10A -75.24(17) . . . . ?
C25A N6A C9A C10A 50.47(19) . . . . ?
C8A N6A C9A C6A 41.93(17) . . . . ?
C25A N6A C9A C6A 167.65(15) . . . . ?
C5A C6A C9A N6A 95.42(15) . . . . ?
C7A C6A C9A N6A -22.43(18) . . . . ?
S1A C6A C9A N6A -147.95(12) . . . . ?
C5A C6A C9A C16A -30.30(18) . . . . ?
C7A C6A C9A C16A -148.14(15) . . . . ?
S1A C6A C9A C16A 86.33(16) . . . . ?
C5A C6A C9A C10A -143.46(14) . . . . ?
C7A C6A C9A C10A 98.69(16) . . . . ?
S1A C6A C9A C10A -26.83(18) . . . . ?
C11A N7A C10A O3A -177.15(17) . . . . ?
C11A N7A C10A C9A 2.30(18) . . . . ?
N6A C9A C10A O3A 51.0(2) . . . . ?
C16A C9A C10A O3A 175.33(16) . . . . ?
C6A C9A C10A O3A -62.7(2) . . . . ?
N6A C9A C10A N7A -128.45(15) . . . . ?
C16A C9A C10A N7A -4.12(16) . . . . ?
C6A C9A C10A N7A 117.88(15) . . . . ?
C10A N7A C11A C12A 179.58(17) . . . . ?
C10A N7A C11A C16A 0.73(19) . . . . ?
C16A C11A C12A C13A 0.4(2) . . . . ?
N7A C11A C12A C13A -178.28(16) . . . . ?
C11A C12A C13A C14A 2.0(3) . . . . ?
C12A C13A C14A C15A -1.5(3) . . . . ?
C13A C14A C15A C16A -1.4(2) . . . . ?
C14A C15A C16A C11A 3.7(2) . . . . ?
C14A C15A C16A C9A -177.34(16) . . . . ?
C12A C11A C16A C15A -3.3(2) . . . . ?
N7A C11A C16A C15A 175.60(14) . . . . ?
C12A C11A C16A C9A 177.51(15) . . . . ?
N7A C11A C16A C9A -3.55(18) . . . . ?
N6A C9A C16A C15A -50.7(2) . . . . ?
C10A C9A C16A C15A -174.47(16) . . . . ?
C6A C9A C16A C15A 68.4(2) . . . . ?
N6A C9A C16A C11A 128.33(15) . . . . ?
C10A C9A C16A C11A 4.54(16) . . . . ?
C6A C9A C16A C11A -112.60(15) . . . . ?
C8A C7A C17A C18A 148.7(11) . . . . ?
C6A C7A C17A C18A -80.1(14) . . . . ?
C8A C7A C17A C22A -30.1(15) . . . . ?
C6A C7A C17A C22A 101.0(13) . . . . ?
C7A C17A C18A C19A -178.1(10) . . . . ?
C22A C17A C18A C19A 0.8(19) . . . . ?
C7A C17A C18A F1A 4.3(18) . . . . ?
C22A C17A C18A F1A -176.8(11) . . . . ?
C17A C18A C19A C20A -1.4(18) . . . . ?
F1A C18A C19A C20A 176.1(10) . . . . ?
C18A C19A C20A C21A 0.8(18) . . . . ?
C19A C20A C21A C22A 0(2) . . . . ?
C7A C17A C22A C21A 179.4(12) . . . . ?
C18A C17A C22A C21A 0(2) . . . . ?
C20A C21A C22A C17A -1(2) . . . . ?
C8A C7A C17' C18' 148.6(6) . . . . ?
C6A C7A C17' C18' -92.7(7) . . . . ?
C8A C7A C17' C22' -34.3(8) . . . . ?
C6A C7A C17' C22' 84.3(8) . . . . ?
C22' C17' C18' F1' -174.8(7) . . . . ?
C7A C17' C18' F1' 2.6(10) . . . . ?
C22' C17' C18' C19' 4.5(12) . . . . ?
C7A C17' C18' C19' -178.1(6) . . . . ?
F1' C18' C19' C20' 177.3(6) . . . . ?
C17' C18' C19' C20' -2.0(11) . . . . ?
C18' C19' C20' C21' -0.7(9) . . . . ?
C19' C20' C21' C22' 0.7(10) . . . . ?
C18' C17' C22' C21' -4.4(11) . . . . ?
C7A C17' C22' C21' 178.4(6) . . . . ?
C20' C21' C22' C17' 2.1(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3N O1S 0.98(2) 1.93(2) 2.8354(18) 153.4(17) 2_645
N7 H7N O1 0.83(2) 2.07(2) 2.8845(17) 167(2) 2_645
N7A H7NA O1A 0.90(2) 1.96(3) 2.8272(19) 162(2) 2
O1S H1SO O2A 0.99(3) 1.80(3) 2.7365(18) 157(3) .
O2S H2SO O1 0.98(4) 1.83(4) 2.799(2) 168(3) .

_refine_diff_density_max         0.578
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.059




# start Validation Reply Form
_vrf_CHEMW03_dv12                
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PROBLEM: Wrong formula and formula weight
RESPONSE: Heavily disordered solvating methanol molecules were removed using 
SQUEEZE method.
;
# end Validation Reply Form
