# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2151550'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-03-30 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(C21 H15 F4 N5 O2 S), C3 H7 N O'
_chemical_formula_sum            'C45 H37 F8 N11 O5 S2'
_chemical_formula_weight         1027.97

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                   12.3974(9)
_cell_length_b                   17.3988(15)
_cell_length_c                   23.2772(17)
_cell_angle_alpha                68.343(3)
_cell_angle_beta                 81.611(3)
_cell_angle_gamma                89.765(3)
_cell_volume                     4609.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9075
_cell_measurement_theta_min      2.327
_cell_measurement_theta_max      26.368

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_F_000             2112
_exptl_transmission_factor_min   0.6420
_exptl_transmission_factor_max   0.8620
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.208
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39826
_diffrn_reflns_av_unetI/netI     0.1126
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.842
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.050
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             15816
_reflns_number_gt                9830
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0953P)²+28.5160P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         15816
_refine_ls_number_parameters     1332
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1575
_refine_ls_R_factor_gt           0.1035
_refine_ls_wR_factor_ref         0.2736
_refine_ls_wR_factor_gt          0.2444
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.011
_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 0.72188(16) 0.52896(12) 0.68045(10) 0.0295(5) Uani 1 1 d . . . . .
F1A F 0.4166(9) 0.5626(6) 0.5259(5) 0.030(4) Uani 0.406(13) 1 d . . P A 1
F1B F 0.4055(7) 0.7691(4) 0.6153(4) 0.040(3) Uani 0.594(13) 1 d . . P A 2
F11 F 1.0731(4) 0.3533(3) 0.7629(3) 0.0540(14) Uani 1 1 d . . . . .
F12 F 1.0092(4) 0.2279(3) 0.7996(3) 0.0506(14) Uani 1 1 d . . . . .
F13 F 0.9654(4) 0.3131(3) 0.7141(3) 0.0529(14) Uani 1 1 d . . . . .
O11 O 0.4004(5) 0.8018(3) 0.4891(3) 0.0375(14) Uani 1 1 d . . . . .
O12 O 0.4888(5) 0.3306(4) 0.8704(3) 0.0383(14) Uani 1 1 d . . . . .
N11 N 0.2796(6) 0.7035(4) 0.4907(3) 0.0369(17) Uani 1 1 d D . . . .
H11 H 0.249(7) 0.655(4) 0.510(4) 0.044 Uiso 1 1 d D U . . .
N12 N 0.5090(5) 0.4962(4) 0.7277(3) 0.0257(14) Uani 1 1 d . . . . .
N13 N 0.6163(5) 0.4168(4) 0.7903(3) 0.0238(14) Uani 1 1 d . . . . .
N14 N 0.8094(5) 0.3490(4) 0.9017(3) 0.0312(16) Uani 1 1 d . . . . .
N15 N 1.0634(6) 0.2866(5) 0.9214(4) 0.050(2) Uani 1 1 d . . . . .
C10 C 0.3599(6) 0.7306(4) 0.5124(3) 0.0219(16) Uani 1 1 d . . . . .
C11 C 0.3971(6) 0.6685(4) 0.5687(4) 0.0253(17) Uani 1 1 d . . . . .
C12 C 0.4168(6) 0.5878(4) 0.5742(4) 0.0251(17) Uani 1 1 d . . . . .
H12 H 0.403615 0.570612 0.541498 0.030 Uiso 0.594(13) 1 calc R U P A 2
C13 C 0.4548(6) 0.5316(5) 0.6255(4) 0.0283(18) Uani 1 1 d . . . . .
H13 H 0.467629 0.476746 0.627813 0.034 Uiso 1 1 calc R U . . .
C14 C 0.4737(6) 0.5555(4) 0.6730(3) 0.0219(16) Uani 1 1 d . . . . .
C15 C 0.4543(6) 0.6351(4) 0.6703(4) 0.0258(17) Uani 1 1 d . . . . .
H15 H 0.464746 0.651165 0.704020 0.031 Uiso 1 1 calc R U . . .
C16 C 0.4196(6) 0.6905(4) 0.6176(4) 0.0244(17) Uani 1 1 d . . . . .
H16 H 0.410692 0.746037 0.614496 0.029 Uiso 0.406(13) 1 calc R U P A 1
C17 C 0.6159(6) 0.4809(4) 0.7320(4) 0.0240(17) Uani 1 1 d . . . . .
C18 C 0.5112(6) 0.3887(5) 0.8217(4) 0.0282(18) Uani 1 1 d . . . . .
C19 C 0.4348(6) 0.4460(4) 0.7833(4) 0.0243(17) Uani 1 1 d . . . . .
C20 C 0.3312(6) 0.3997(5) 0.7783(4) 0.0286(18) Uani 1 1 d . . . . .
H20A H 0.302636 0.426191 0.738396 0.034 Uiso 1 1 calc R U . . .
H20B H 0.338929 0.339732 0.788177 0.034 Uiso 1 1 calc R U . . .
C21 C 0.2699(6) 0.4204(5) 0.8330(4) 0.0317(19) Uani 1 1 d . . . . .
H21A H 0.266774 0.374954 0.874330 0.038 Uiso 1 1 calc R U . . .
H21B H 0.196574 0.441183 0.826209 0.038 Uiso 1 1 calc R U . . .
C22 C 0.3593(6) 0.4897(5) 0.8197(4) 0.0276(18) Uani 1 1 d . . . . .
H22A H 0.339888 0.545547 0.793373 0.033 Uiso 1 1 calc R U . . .
H22B H 0.385619 0.490374 0.857727 0.033 Uiso 1 1 calc R U . . .
C23 C 0.7209(7) 0.3772(5) 0.8755(4) 0.0303(19) Uani 1 1 d . . . . .
H23 H 0.661982 0.393090 0.898983 0.036 Uiso 1 1 calc R U . . .
C24 C 0.7121(6) 0.3842(4) 0.8145(4) 0.0256(17) Uani 1 1 d . . . . .
C25 C 0.7959(6) 0.3593(4) 0.7808(4) 0.0271(18) Uani 1 1 d . . . . .
H25 H 0.790475 0.362187 0.739822 0.032 Uiso 1 1 calc R U . . .
C26 C 0.8877(6) 0.3302(4) 0.8070(4) 0.0252(17) Uani 1 1 d . . . . .
C27 C 0.8925(6) 0.3287(4) 0.8671(4) 0.0274(18) Uani 1 1 d . . . . .
C28 C 0.9825(7) 0.3066(5) 0.7711(4) 0.036(2) Uani 1 1 d . . . . .
C29 C 0.9880(7) 0.3041(5) 0.8967(4) 0.035(2) Uani 1 1 d . . . . .
C91 C 0.2374(8) 0.7529(5) 0.4350(4) 0.046(2) Uani 1 1 d . . . . .
H91A H 0.202677 0.716584 0.418595 0.069 Uiso 1 1 calc R U . . .
H91B H 0.297405 0.786573 0.403508 0.069 Uiso 1 1 calc R U . . .
H91C H 0.183523 0.789327 0.444917 0.069 Uiso 1 1 calc R U . . .
S2 S 0.69159(16) 1.02630(12) 0.67985(10) 0.0283(5) Uani 1 1 d . . . . .
F2A F 1.0667(7) 1.0593(5) 0.5250(4) 0.030(3) Uani 0.526(13) 1 d . . P B 3
F2B F 1.0493(8) 1.2713(5) 0.6079(5) 0.037(3) Uani 0.474(13) 1 d . . P B 4
F21 F 0.3582(5) 0.7129(3) 0.8306(4) 0.076(2) Uani 1 1 d . . . . .
F22 F 0.4443(5) 0.7848(4) 0.7393(3) 0.077(2) Uani 1 1 d . . . . .
F23 F 0.3019(4) 0.8300(4) 0.7776(3) 0.0613(16) Uani 1 1 d . . . . .
O21 O 1.1003(4) 1.2979(3) 0.4801(3) 0.0382(14) Uani 1 1 d . . . . .
O22 O 0.8159(5) 0.8582(4) 0.8819(3) 0.0499(17) Uani 1 1 d . . . . .
N21 N 1.2176(6) 1.1992(4) 0.4805(3) 0.0374(17) Uani 1 1 d D . . . .
H21 H 1.237(7) 1.151(4) 0.502(4) 0.045 Uiso 1 1 d D U . . .
N22 N 0.8773(5) 1.0051(4) 0.7300(3) 0.0215(14) Uani 1 1 d . . . . .
N23 N 0.7350(5) 0.9322(4) 0.7951(3) 0.0261(15) Uani 1 1 d . . . . .
N24 N 0.4778(6) 0.8806(4) 0.9028(3) 0.0348(17) Uani 1 1 d . . . . .
N25 N 0.2195(7) 0.8012(6) 0.9288(4) 0.059(2) Uani 1 1 d . . . . .
C30 C 1.1323(6) 1.2270(5) 0.5042(4) 0.0288(18) Uani 1 1 d . . . . .
C31 C 1.0688(6) 1.1679(4) 0.5643(4) 0.0225(17) Uani 1 1 d . . . . .
C32 C 1.0415(6) 1.0866(5) 0.5722(4) 0.0269(18) Uani 1 1 d . . . . .
H32 H 1.066984 1.067574 0.539559 0.032 Uiso 0.474(13) 1 calc R U P B 4
C33 C 0.9786(6) 1.0328(4) 0.6261(4) 0.0237(17) Uani 1 1 d . . . . .
H33 H 0.961136 0.977599 0.630455 0.028 Uiso 1 1 calc R U . . .
C34 C 0.9415(6) 1.0608(4) 0.6737(4) 0.0223(16) Uani 1 1 d . . . . .
C35 C 0.9681(6) 1.1409(4) 0.6675(4) 0.0271(18) Uani 1 1 d . . . . .
H35 H 0.944081 1.159791 0.700436 0.032 Uiso 1 1 calc R U . . .
C36 C 1.0297(6) 1.1926(4) 0.6130(4) 0.0247(17) Uani 1 1 d . . . . .
H36 H 1.046250 1.247944 0.608607 0.030 Uiso 0.526(13) 1 calc R U P B 3
C37 C 0.7694(6) 0.9879(4) 0.7341(4) 0.0229(17) Uani 1 1 d . . . . .
C38 C 0.8230(6) 0.9087(5) 0.8293(4) 0.0325(19) Uani 1 1 d . . . . .
C39 C 0.9217(6) 0.9591(4) 0.7870(4) 0.0223(16) Uani 1 1 d . . . . .
C40 C 1.0204(6) 0.9047(5) 0.7844(4) 0.0317(19) Uani 1 1 d . . . . .
H40A H 1.000285 0.844803 0.798587 0.038 Uiso 1 1 calc R U . . .
H40B H 1.069529 0.924366 0.743700 0.038 Uiso 1 1 calc R U . . .
C41 C 1.0608(7) 0.9303(5) 0.8346(4) 0.0330(19) Uani 1 1 d . . . . .
H41A H 1.139530 0.947322 0.825389 0.040 Uiso 1 1 calc R U . . .
H41B H 1.041066 0.889158 0.877712 0.040 Uiso 1 1 calc R U . . .
C42 C 0.9854(6) 1.0038(5) 0.8182(4) 0.0320(19) Uani 1 1 d . . . . .
H42A H 0.942300 1.010593 0.855115 0.038 Uiso 1 1 calc R U . . .
H42B H 1.022791 1.056820 0.788790 0.038 Uiso 1 1 calc R U . . .
C43 C 0.5794(7) 0.9061(5) 0.8756(4) 0.034(2) Uani 1 1 d . . . . .
H43 H 0.622992 0.930580 0.895366 0.041 Uiso 1 1 calc R U . . .
C44 C 0.6251(6) 0.8994(5) 0.8210(4) 0.0274(18) Uani 1 1 d . . . . .
C45 C 0.5668(6) 0.8603(4) 0.7926(4) 0.0275(18) Uani 1 1 d . . . . .
H45 H 0.598352 0.853576 0.755114 0.033 Uiso 1 1 calc R U . . .
C46 C 0.4605(6) 0.8311(5) 0.8205(4) 0.0306(19) Uani 1 1 d . . . . .
C47 C 0.4203(7) 0.8436(5) 0.8748(4) 0.033(2) Uani 1 1 d . . . . .
C48 C 0.3921(8) 0.7899(6) 0.7918(5) 0.044(2) Uani 1 1 d . . . . .
C49 C 0.3083(7) 0.8198(6) 0.9054(4) 0.040(2) Uani 1 1 d . . . . .
C92 C 1.2841(9) 1.2465(6) 0.4202(4) 0.051(3) Uani 1 1 d . . . . .
H92A H 1.357731 1.225804 0.419281 0.077 Uiso 1 1 calc R U . . .
H92B H 1.288534 1.305177 0.414571 0.077 Uiso 1 1 calc R U . . .
H92C H 1.250708 1.240378 0.386394 0.077 Uiso 1 1 calc R U . . .
S3 S 0.56971(17) 0.32545(12) 0.67950(11) 0.0339(5) Uani 1 1 d . . . . .
F3A F 0.1582(8) 0.4339(5) 0.6335(4) 0.051(3) Uani 0.591(14) 1 d . . P C 5
F3B F 0.3385(10) 0.3862(8) 0.4685(5) 0.046(4) Uani 0.409(14) 1 d . . P C 6
F31 F 0.4833(4) 0.1270(3) 0.9661(2) 0.0464(13) Uani 1 1 d . . . . .
F32 F 0.6169(4) 0.0500(3) 0.9930(2) 0.0457(13) Uani 1 1 d . . . . .
F33 F 0.6388(4) 0.1814(3) 0.9659(2) 0.0456(13) Uani 1 1 d . . . . .
O31 O 0.1839(6) 0.5489(4) 0.5180(4) 0.074(3) Uani 1 1 d . . . . .
N31 N 0.1434(6) 0.4705(4) 0.4654(3) 0.0329(16) Uani 1 1 d D . . . .
H31 H 0.129(7) 0.421(3) 0.468(4) 0.039 Uiso 1 1 d D U . . .
N32 N 0.4166(5) 0.2250(4) 0.6686(3) 0.0290(15) Uani 1 1 d . . . . .
N33 N 0.5132(5) 0.1631(4) 0.7429(3) 0.0267(15) Uani 1 1 d . . . . .
N34 N 0.7741(5) 0.1474(4) 0.8024(3) 0.0279(15) Uani 1 1 d . . . . .
N35 N 0.8862(7) 0.1096(5) 0.9338(4) 0.0443(19) Uani 1 1 d . . . . .
O32 O 0.4253(4) 0.0330(3) 0.7889(3) 0.0340(13) Uani 1 1 d . . . . .
C50 C 0.1881(7) 0.4832(5) 0.5089(4) 0.036(2) Uani 1 1 d . . . . .
C51 C 0.2463(6) 0.4131(4) 0.5490(4) 0.0291(19) Uani 1 1 d . . . . .
C52 C 0.2304(6) 0.3923(5) 0.6137(4) 0.033(2) Uani 1 1 d . . . . .
H52 H 0.179912 0.421981 0.631173 0.039 Uiso 0.409(14) 1 calc R U P C 6
C53 C 0.2844(6) 0.3311(5) 0.6531(4) 0.0300(18) Uani 1 1 d . . . . .
H53 H 0.269640 0.316932 0.697120 0.036 Uiso 1 1 calc R U . . .
C54 C 0.3613(6) 0.2902(4) 0.6269(4) 0.0262(18) Uani 1 1 d . . . . .
C55 C 0.3796(7) 0.3065(5) 0.5641(4) 0.035(2) Uani 1 1 d . . . . .
H55 H 0.430553 0.276457 0.547155 0.042 Uiso 1 1 calc R U . . .
C56 C 0.3217(6) 0.3682(5) 0.5252(4) 0.035(2) Uani 1 1 d . . . . .
H56 H 0.333963 0.380019 0.481508 0.042 Uiso 0.591(14) 1 calc R U P C 5
C57 C 0.4979(6) 0.2379(4) 0.6958(4) 0.0283(18) Uani 1 1 d . . . . .
C58 C 0.4345(6) 0.1017(5) 0.7488(4) 0.0277(18) Uani 1 1 d . . . . .
C59 C 0.3706(6) 0.1391(4) 0.6965(4) 0.0252(17) Uani 1 1 d . . . . .
C60 C 0.2458(6) 0.1215(5) 0.7157(4) 0.034(2) Uani 1 1 d . . . . .
H60A H 0.202529 0.167084 0.692037 0.040 Uiso 1 1 calc R U . . .
H60B H 0.220913 0.103507 0.761326 0.040 Uiso 1 1 calc R U . . .
C61 C 0.2555(7) 0.0482(5) 0.6912(4) 0.038(2) Uani 1 1 d . . . . .
H61A H 0.257033 -0.007081 0.724501 0.046 Uiso 1 1 calc R U . . .
H61B H 0.201901 0.048176 0.663616 0.046 Uiso 1 1 calc R U . . .
C62 C 0.3699(6) 0.0872(5) 0.6557(4) 0.0292(18) Uani 1 1 d . . . . .
H62A H 0.427578 0.046728 0.661236 0.035 Uiso 1 1 calc R U . . .
H62B H 0.370356 0.120761 0.610824 0.035 Uiso 1 1 calc R U . . .
C63 C 0.7003(6) 0.1574(4) 0.7641(4) 0.0275(18) Uani 1 1 d . . . . .
H63 H 0.724538 0.167471 0.721172 0.033 Uiso 1 1 calc R U . . .
C64 C 0.5882(6) 0.1533(4) 0.7856(4) 0.0261(18) Uani 1 1 d . . . . .
C65 C 0.5513(6) 0.1409(5) 0.8462(4) 0.0262(17) Uani 1 1 d . . . . .
H65 H 0.475235 0.138704 0.860599 0.031 Uiso 1 1 calc R U . . .
C66 C 0.6255(6) 0.1315(5) 0.8868(4) 0.0291(18) Uani 1 1 d . . . . .
C67 C 0.7357(6) 0.1342(4) 0.8625(4) 0.0263(18) Uani 1 1 d . . . . .
C68 C 0.5907(7) 0.1228(5) 0.9531(4) 0.035(2) Uani 1 1 d . . . . .
C69 C 0.8196(7) 0.1217(5) 0.9023(4) 0.036(2) Uani 1 1 d . . . . .
C93 C 0.0873(8) 0.5372(6) 0.4222(4) 0.047(2) Uani 1 1 d . . . . .
H93A H 0.027308 0.512921 0.410164 0.071 Uiso 1 1 calc R U . . .
H93B H 0.139265 0.568514 0.384738 0.071 Uiso 1 1 calc R U . . .
H93C H 0.058146 0.574327 0.442963 0.071 Uiso 1 1 calc R U . . .
S4 S 0.83519(16) 0.82020(12) 0.70774(11) 0.0343(5) Uani 1 1 d . . . . .
F4A F 1.2978(7) 0.9088(5) 0.6500(4) 0.049(3) Uani 0.613(14) 1 d . . P D 7
F4B F 1.1559(10) 0.8872(8) 0.4858(5) 0.037(4) Uani 0.387(14) 1 d . . P D 8
F41 F 0.7936(6) 0.6806(5) 0.9756(3) 0.078(2) Uani 1 1 d . . . . .
F42 F 0.6595(6) 0.5924(4) 1.0221(3) 0.0741(19) Uani 1 1 d . . . . .
F43 F 0.6290(6) 0.7200(4) 0.9775(3) 0.0701(18) Uani 1 1 d . . . . .
O41 O 1.3018(5) 1.0433(3) 0.5359(3) 0.0386(14) Uani 1 1 d . . . . .
O42 O 0.9194(5) 0.5241(3) 0.8050(3) 0.0421(15) Uani 1 1 d . . . . .
N41 N 1.3597(6) 0.9704(4) 0.4754(3) 0.0305(16) Uani 1 1 d D . . . .
H41 H 1.382(7) 0.926(4) 0.473(4) 0.037 Uiso 1 1 d D U . . .
N42 N 0.9921(5) 0.7200(4) 0.6900(3) 0.0278(15) Uani 1 1 d . . . . .
N43 N 0.8574(5) 0.6568(4) 0.7662(3) 0.0284(15) Uani 1 1 d . . . . .
N44 N 0.5770(6) 0.6062(6) 0.8502(4) 0.058(2) Uani 1 1 d . . . . .
N45 N 0.4124(9) 0.5888(6) 0.9851(5) 0.081(3) Uani 1 1 d . . . . .
C70 C 1.2981(7) 0.9789(5) 0.5245(4) 0.0318(19) Uani 1 1 d . . . . .
C71 C 1.2211(6) 0.9075(5) 0.5667(4) 0.0258(17) Uani 1 1 d . . . . .
C72 C 1.2158(7) 0.8799(5) 0.6308(4) 0.0328(19) Uani 1 1 d . . . . .
H72 H 1.266134 0.903832 0.647365 0.039 Uiso 0.387(14) 1 calc R U P D 8
C73 C 1.1416(6) 0.8200(5) 0.6713(4) 0.0307(19) Uani 1 1 d . . . . .
H73 H 1.140575 0.802298 0.715149 0.037 Uiso 1 1 calc R U . . .
C74 C 1.0682(6) 0.7855(4) 0.6474(4) 0.0265(18) Uani 1 1 d . . . . .
C75 C 1.0706(6) 0.8096(5) 0.5837(4) 0.035(2) Uani 1 1 d . . . . .
H75 H 1.020719 0.784564 0.567622 0.042 Uiso 1 1 calc R U . . .
C76 C 1.1469(7) 0.8706(5) 0.5438(4) 0.036(2) Uani 1 1 d . . . . .
H76 H 1.148806 0.887716 0.499877 0.043 Uiso 0.613(14) 1 calc R U P D 7
C77 C 0.8971(6) 0.7323(5) 0.7214(4) 0.0284(18) Uani 1 1 d . . . . .
C78 C 0.9310(7) 0.5950(5) 0.7674(4) 0.0316(19) Uani 1 1 d . . . . .
C79 C 1.0200(6) 0.6327(5) 0.7133(4) 0.0287(18) Uani 1 1 d . . . . .
C80 C 1.1378(7) 0.6126(5) 0.7262(4) 0.0368(13) Uani 1 1 d D . . . .
H80C H 1.190904 0.660800 0.705885 0.044 Uiso 0.633(18) 1 calc R U P E 10
H80D H 1.143128 0.585374 0.771245 0.044 Uiso 0.633(18) 1 calc R U P E 10
H80A H 1.142785 0.563104 0.764172 0.044 Uiso 0.367(18) 1 calc R U P E 9
H80B H 1.182829 0.660370 0.724811 0.044 Uiso 0.367(18) 1 calc R U P E 9
C81A C 1.1538(14) 0.5962(18) 0.6646(11) 0.0368(13) Uani 0.367(18) 1 d D . P E 9
H81A H 1.191277 0.643288 0.628204 0.044 Uiso 0.367(18) 1 calc R U P E 9
H81B H 1.190012 0.544178 0.668135 0.044 Uiso 0.367(18) 1 calc R U P E 9
C81B C 1.1424(11) 0.5531(10) 0.6919(8) 0.0368(13) Uani 0.633(18) 1 d D . P E 10
H81C H 1.133478 0.493986 0.720018 0.044 Uiso 0.633(18) 1 calc R U P E 10
H81D H 1.207175 0.563205 0.659168 0.044 Uiso 0.633(18) 1 calc R U P E 10
C82 C 1.0348(7) 0.5895(5) 0.6655(4) 0.0368(13) Uani 1 1 d D . . . .
H82C H 1.047625 0.628342 0.621323 0.044 Uiso 0.633(18) 1 calc R U P E 10
H82D H 0.976313 0.546956 0.672655 0.044 Uiso 0.633(18) 1 calc R U P E 10
H82A H 1.003380 0.531874 0.682418 0.044 Uiso 0.367(18) 1 calc R U P E 9
H82B H 1.010847 0.621991 0.625095 0.044 Uiso 0.367(18) 1 calc R U P E 9
C83 C 0.6650(8) 0.6196(6) 0.8077(5) 0.050(3) Uani 1 1 d . . . . .
H83 H 0.658389 0.609515 0.770855 0.060 Uiso 1 1 calc R U . . .
C84 C 0.7665(6) 0.6472(4) 0.8129(4) 0.0272(18) Uani 1 1 d . . . . .
C85 C 0.7743(7) 0.6621(5) 0.8665(4) 0.036(2) Uani 1 1 d . . . . .
H85 H 0.841596 0.682854 0.871625 0.043 Uiso 1 1 calc R U . . .
C86 C 0.6855(7) 0.6470(5) 0.9123(4) 0.0331(19) Uani 1 1 d . . . . .
C87 C 0.5887(7) 0.6193(5) 0.9019(5) 0.043(2) Uani 1 1 d . . . . .
C88 C 0.6912(10) 0.6607(7) 0.9718(4) 0.056(3) Uani 1 1 d . . . . .
C89 C 0.4897(9) 0.6023(7) 0.9485(6) 0.058(3) Uani 1 1 d . . . . .
C94 C 1.4350(8) 1.0352(5) 0.4314(4) 0.041(2) Uani 1 1 d . . . . .
H94A H 1.501102 1.010932 0.418476 0.061 Uiso 1 1 calc R U . . .
H94B H 1.454338 1.073119 0.451195 0.061 Uiso 1 1 calc R U . . .
H94C H 1.400905 1.065799 0.394726 0.061 Uiso 1 1 calc R U . . .
O1 O 0.0420(6) 0.6851(4) 0.8342(4) 0.0535(18) Uani 1 1 d . . . . .
N1 N 0.0974(7) 0.6093(5) 0.9265(4) 0.051(2) Uani 1 1 d . . . . .
C1 C 0.0590(8) 0.6750(7) 0.8876(6) 0.061(3) Uani 1 1 d . . . . .
H1 H 0.042648 0.719151 0.901665 0.073 Uiso 1 1 calc R U . . .
C2 C 0.1238(12) 0.5392(8) 0.9096(6) 0.087(4) Uani 1 1 d . . . . .
H2A H 0.077961 0.536758 0.879299 0.131 Uiso 1 1 calc R U . . .
H2B H 0.110511 0.488302 0.947030 0.131 Uiso 1 1 calc R U . . .
H2C H 0.200833 0.544715 0.890867 0.131 Uiso 1 1 calc R U . . .
C3 C 0.1209(11) 0.6050(9) 0.9865(6) 0.082(4) Uani 1 1 d . . . . .
H3A H 0.113528 0.659522 0.989448 0.123 Uiso 1 1 calc R U . . .
H3B H 0.195663 0.587883 0.990829 0.123 Uiso 1 1 calc R U . . .
H3C H 0.069541 0.564534 1.019882 0.123 Uiso 1 1 calc R U . . .
O2 O 0.2974(5) 0.1896(4) 0.8217(3) 0.0436(15) Uani 1 1 d . . . . .
N2 N 0.2181(6) 0.1166(4) 0.9221(4) 0.0405(18) Uani 1 1 d . . . . .
C4 C 0.2677(7) 0.1814(5) 0.8770(5) 0.041(2) Uani 1 1 d . . . . .
H4 H 0.282926 0.227513 0.887618 0.049 Uiso 1 1 calc R U . . .
C5 C 0.1895(10) 0.0436(6) 0.9096(5) 0.059(3) Uani 1 1 d . . . . .
H5A H 0.235505 0.044210 0.871390 0.088 Uiso 1 1 calc R U . . .
H5B H 0.112597 0.043980 0.904112 0.088 Uiso 1 1 calc R U . . .
H5C H 0.201272 -0.006491 0.944865 0.088 Uiso 1 1 calc R U . . .
C6 C 0.1865(10) 0.1141(6) 0.9849(4) 0.057(3) Uani 1 1 d . . . . .
H6A H 0.211448 0.166004 0.987364 0.085 Uiso 1 1 calc R U . . .
H6B H 0.219832 0.067587 1.014142 0.085 Uiso 1 1 calc R U . . .
H6C H 0.106846 0.106939 0.995968 0.085 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
S1 C17 1.635(8) . ?
F1A C12 1.349(12) . ?
F1B C16 1.361(10) . ?
F11 C28 1.337(10) . ?
F12 C28 1.348(9) . ?
F13 C28 1.338(10) . ?
O11 C10 1.230(9) . ?
O12 C18 1.204(9) . ?
N11 C10 1.338(10) . ?
N11 C91 1.438(11) . ?
N11 H11 0.85(5) . ?
N12 C17 1.360(9) . ?
N12 C14 1.437(9) . ?
N12 C19 1.453(10) . ?
N13 C18 1.391(10) . ?
N13 C17 1.404(10) . ?
N13 C24 1.415(9) . ?
N14 C23 1.337(10) . ?
N14 C27 1.342(10) . ?
N15 C29 1.149(11) . ?
C10 C11 1.492(10) . ?
C11 C12 1.385(10) . ?
C11 C16 1.390(11) . ?
C12 C13 1.379(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.367(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(10) . ?
C15 C16 1.377(11) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C19 1.506(11) . ?
C19 C22 1.553(10) . ?
C19 C20 1.560(11) . ?
C20 C21 1.542(11) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.554(11) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.398(11) . ?
C23 H23 0.9500 . ?
C24 C25 1.376(11) . ?
C25 C26 1.375(11) . ?
C25 H25 0.9500 . ?
C26 C27 1.399(11) . ?
C26 C28 1.487(11) . ?
C27 C29 1.442(12) . ?
C91 H91A 0.9800 . ?
C91 H91B 0.9800 . ?
C91 H91C 0.9800 . ?
S2 C37 1.643(8) . ?
F2A C32 1.347(11) . ?
F2B C36 1.349(11) . ?
F21 C48 1.336(11) . ?
F22 C48 1.329(11) . ?
F23 C48 1.333(11) . ?
O21 C30 1.243(9) . ?
O22 C38 1.205(10) . ?
N21 C30 1.297(10) . ?
N21 C92 1.463(11) . ?
N21 H21 0.85(5) . ?
N22 C37 1.354(9) . ?
N22 C34 1.435(9) . ?
N22 C39 1.459(9) . ?
N23 C37 1.395(10) . ?
N23 C38 1.415(10) . ?
N23 C44 1.434(10) . ?
N24 C43 1.323(10) . ?
N24 C47 1.339(11) . ?
N25 C49 1.144(11) . ?
C30 C31 1.502(11) . ?
C31 C36 1.379(11) . ?
C31 C32 1.393(10) . ?
C32 C33 1.383(11) . ?
C32 H32 0.9500 . ?
C33 C34 1.387(10) . ?
C33 H33 0.9500 . ?
C34 C35 1.383(10) . ?
C35 C36 1.373(11) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C38 C39 1.502(11) . ?
C39 C42 1.529(10) . ?
C39 C40 1.553(10) . ?
C40 C41 1.540(11) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.545(11) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.359(11) . ?
C43 H43 0.9500 . ?
C44 C45 1.378(11) . ?
C45 C46 1.390(11) . ?
C45 H45 0.9500 . ?
C46 C47 1.384(12) . ?
C46 C48 1.484(12) . ?
C47 C49 1.451(12) . ?
C92 H92A 0.9800 . ?
C92 H92B 0.9800 . ?
C92 H92C 0.9800 . ?
S3 C57 1.655(8) . ?
F3A C52 1.288(11) . ?
F3B C56 1.226(14) . ?
F31 C68 1.329(9) . ?
F32 C68 1.337(9) . ?
F33 C68 1.328(9) . ?
O31 C50 1.237(10) . ?
N31 C50 1.308(11) . ?
N31 C93 1.475(10) . ?
N31 H31 0.85(5) . ?
N32 C57 1.327(10) . ?
N32 C54 1.440(9) . ?
N32 C59 1.471(9) . ?
N33 C57 1.392(10) . ?
N33 C58 1.403(10) . ?
N33 C64 1.424(10) . ?
N34 C63 1.336(10) . ?
N34 C67 1.344(10) . ?
N35 C69 1.152(11) . ?
O32 C58 1.208(9) . ?
C50 C51 1.492(11) . ?
C51 C52 1.396(12) . ?
C51 C56 1.397(11) . ?
C52 C53 1.370(11) . ?
C52 H52 0.9500 . ?
C53 C54 1.391(11) . ?
C53 H53 0.9500 . ?
C54 C55 1.367(12) . ?
C55 C56 1.397(11) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C58 C59 1.492(11) . ?
C59 C62 1.534(10) . ?
C59 C60 1.546(11) . ?
C60 C61 1.575(12) . ?
C60 H60A 0.9900 . ?
C60 H60B 0.9900 . ?
C61 C62 1.551(11) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 C64 1.399(11) . ?
C63 H63 0.9500 . ?
C64 C65 1.355(11) . ?
C65 C66 1.380(11) . ?
C65 H65 0.9500 . ?
C66 C67 1.394(11) . ?
C66 C68 1.492(12) . ?
C67 C69 1.456(12) . ?
C93 H93A 0.9800 . ?
C93 H93B 0.9800 . ?
C93 H93C 0.9800 . ?
S4 C77 1.653(8) . ?
F4A C72 1.338(11) . ?
F4B C76 1.260(14) . ?
F41 C88 1.341(13) . ?
F42 C88 1.334(11) . ?
F43 C88 1.319(13) . ?
O41 C70 1.246(9) . ?
O42 C78 1.215(9) . ?
N41 C70 1.334(10) . ?
N41 C94 1.438(10) . ?
N41 H41 0.84(5) . ?
N42 C77 1.353(10) . ?
N42 C74 1.440(10) . ?
N42 C79 1.470(9) . ?
N43 C77 1.378(10) . ?
N43 C78 1.402(10) . ?
N43 C84 1.410(10) . ?
N44 C83 1.319(12) . ?
N44 C87 1.334(12) . ?
N45 C89 1.147(13) . ?
C70 C71 1.502(11) . ?
C71 C72 1.379(12) . ?
C71 C76 1.394(11) . ?
C72 C73 1.360(11) . ?
C72 H72 0.9500 . ?
C73 C74 1.377(11) . ?
C73 H73 0.9500 . ?
C74 C75 1.380(11) . ?
C75 C76 1.382(12) . ?
C75 H75 0.9500 . ?
C76 H76 0.9500 . ?
C78 C79 1.491(12) . ?
C79 C80 1.547(11) . ?
C79 C82 1.547(11) . ?
C80 C81B 1.521(14) . ?
C80 C81A 1.549(19) . ?
C80 H80C 0.9900 . ?
C80 H80D 0.9900 . ?
C80 H80A 0.9900 . ?
C80 H80B 0.9900 . ?
C81A C82 1.477(18) . ?
C81A H81A 0.9900 . ?
C81A H81B 0.9900 . ?
C81B C82 1.583(14) . ?
C81B H81C 0.9900 . ?
C81B H81D 0.9900 . ?
C82 H82C 0.9900 . ?
C82 H82D 0.9900 . ?
C82 H82A 0.9900 . ?
C82 H82B 0.9900 . ?
C83 C84 1.386(12) . ?
C83 H83 0.9500 . ?
C84 C85 1.383(11) . ?
C85 C86 1.367(12) . ?
C85 H85 0.9500 . ?
C86 C87 1.380(13) . ?
C86 C88 1.502(13) . ?
C87 C89 1.466(15) . ?
C94 H94A 0.9800 . ?
C94 H94B 0.9800 . ?
C94 H94C 0.9800 . ?
O1 C1 1.241(13) . ?
N1 C1 1.308(14) . ?
N1 C2 1.437(13) . ?
N1 C3 1.442(13) . ?
C1 H1 0.9500 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
O2 C4 1.241(11) . ?
N2 C4 1.302(12) . ?
N2 C6 1.443(12) . ?
N2 C5 1.459(11) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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
C10 N11 C91 123.4(7) . . ?
C10 N11 H11 121(6) . . ?
C91 N11 H11 116(6) . . ?
C17 N12 C14 123.0(6) . . ?
C17 N12 C19 113.4(6) . . ?
C14 N12 C19 123.6(6) . . ?
C18 N13 C17 112.1(6) . . ?
C18 N13 C24 123.7(6) . . ?
C17 N13 C24 124.3(6) . . ?
C23 N14 C27 117.8(7) . . ?
O11 C10 N11 123.6(7) . . ?
O11 C10 C11 120.9(7) . . ?
N11 C10 C11 115.5(7) . . ?
C12 C11 C16 116.1(7) . . ?
C12 C11 C10 122.7(7) . . ?
C16 C11 C10 121.0(6) . . ?
F1A C12 C13 114.8(7) . . ?
F1A C12 C11 122.0(8) . . ?
C13 C12 C11 122.4(7) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C14 C13 C12 119.4(7) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.7(7) . . ?
C13 C14 N12 119.6(6) . . ?
C15 C14 N12 119.7(7) . . ?
C16 C15 C14 118.5(7) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
F1B C16 C15 117.0(7) . . ?
F1B C16 C11 120.1(7) . . ?
C15 C16 C11 122.8(7) . . ?
C15 C16 H16 118.6 . . ?
C11 C16 H16 118.6 . . ?
N12 C17 N13 105.8(6) . . ?
N12 C17 S1 127.0(6) . . ?
N13 C17 S1 127.2(6) . . ?
O12 C18 N13 125.3(7) . . ?
O12 C18 C19 128.4(7) . . ?
N13 C18 C19 106.3(6) . . ?
N12 C19 C18 101.9(6) . . ?
N12 C19 C22 119.0(6) . . ?
C18 C19 C22 113.8(6) . . ?
N12 C19 C20 121.1(6) . . ?
C18 C19 C20 113.1(6) . . ?
C22 C19 C20 88.5(6) . . ?
C21 C20 C19 88.1(6) . . ?
C21 C20 H20A 114.0 . . ?
C19 C20 H20A 114.0 . . ?
C21 C20 H20B 114.0 . . ?
C19 C20 H20B 114.0 . . ?
H20A C20 H20B 111.2 . . ?
C20 C21 C22 89.1(6) . . ?
C20 C21 H21A 113.8 . . ?
C22 C21 H21A 113.8 . . ?
C20 C21 H21B 113.8 . . ?
C22 C21 H21B 113.8 . . ?
H21A C21 H21B 111.0 . . ?
C19 C22 C21 87.9(6) . . ?
C19 C22 H22A 114.0 . . ?
C21 C22 H22A 114.0 . . ?
C19 C22 H22B 114.0 . . ?
C21 C22 H22B 114.0 . . ?
H22A C22 H22B 111.2 . . ?
N14 C23 C24 122.3(7) . . ?
N14 C23 H23 118.8 . . ?
C24 C23 H23 118.8 . . ?
C25 C24 C23 119.1(7) . . ?
C25 C24 N13 122.9(7) . . ?
C23 C24 N13 118.0(7) . . ?
C26 C25 C24 119.5(7) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C27 118.0(7) . . ?
C25 C26 C28 121.3(7) . . ?
C27 C26 C28 120.6(7) . . ?
N14 C27 C26 123.2(7) . . ?
N14 C27 C29 114.9(7) . . ?
C26 C27 C29 121.9(7) . . ?
F11 C28 F13 106.6(7) . . ?
F11 C28 F12 105.4(7) . . ?
F13 C28 F12 105.7(7) . . ?
F11 C28 C26 112.3(7) . . ?
F13 C28 C26 113.0(7) . . ?
F12 C28 C26 113.1(7) . . ?
N15 C29 C27 177.4(9) . . ?
N11 C91 H91A 109.5 . . ?
N11 C91 H91B 109.5 . . ?
H91A C91 H91B 109.5 . . ?
N11 C91 H91C 109.5 . . ?
H91A C91 H91C 109.5 . . ?
H91B C91 H91C 109.5 . . ?
C30 N21 C92 123.6(7) . . ?
C30 N21 H21 118(6) . . ?
C92 N21 H21 118(6) . . ?
C37 N22 C34 122.3(6) . . ?
C37 N22 C39 113.7(6) . . ?
C34 N22 C39 123.9(6) . . ?
C37 N23 C38 111.9(6) . . ?
C37 N23 C44 125.5(6) . . ?
C38 N23 C44 122.6(6) . . ?
C43 N24 C47 116.4(7) . . ?
O21 C30 N21 124.3(8) . . ?
O21 C30 C31 119.1(7) . . ?
N21 C30 C31 116.6(7) . . ?
C36 C31 C32 116.7(7) . . ?
C36 C31 C30 121.7(6) . . ?
C32 C31 C30 121.6(7) . . ?
F2A C32 C33 116.6(7) . . ?
F2A C32 C31 121.0(7) . . ?
C33 C32 C31 122.1(7) . . ?
C33 C32 H32 118.9 . . ?
C31 C32 H32 118.9 . . ?
C32 C33 C34 118.8(7) . . ?
C32 C33 H33 120.6 . . ?
C34 C33 H33 120.6 . . ?
C35 C34 C33 120.5(7) . . ?
C35 C34 N22 120.3(7) . . ?
C33 C34 N22 119.1(6) . . ?
C36 C35 C34 118.8(7) . . ?
C36 C35 H35 120.6 . . ?
C34 C35 H35 120.6 . . ?
F2B C36 C35 116.7(8) . . ?
F2B C36 C31 120.2(8) . . ?
C35 C36 C31 123.0(7) . . ?
C35 C36 H36 118.5 . . ?
C31 C36 H36 118.5 . . ?
N22 C37 N23 106.2(6) . . ?
N22 C37 S2 127.8(6) . . ?
N23 C37 S2 125.9(6) . . ?
O22 C38 N23 124.9(8) . . ?
O22 C38 C39 129.1(7) . . ?
N23 C38 C39 106.0(7) . . ?
N22 C39 C38 102.1(6) . . ?
N22 C39 C42 121.1(6) . . ?
C38 C39 C42 113.3(7) . . ?
N22 C39 C40 119.9(6) . . ?
C38 C39 C40 111.7(6) . . ?
C42 C39 C40 89.1(6) . . ?
C41 C40 C39 87.7(6) . . ?
C41 C40 H40A 114.0 . . ?
C39 C40 H40A 114.0 . . ?
C41 C40 H40B 114.0 . . ?
C39 C40 H40B 114.0 . . ?
H40A C40 H40B 111.2 . . ?
C40 C41 C42 89.0(6) . . ?
C40 C41 H41A 113.8 . . ?
C42 C41 H41A 113.8 . . ?
C40 C41 H41B 113.8 . . ?
C42 C41 H41B 113.8 . . ?
H41A C41 H41B 111.0 . . ?
C39 C42 C41 88.4(6) . . ?
C39 C42 H42A 113.9 . . ?
C41 C42 H42A 113.9 . . ?
C39 C42 H42B 113.9 . . ?
C41 C42 H42B 113.9 . . ?
H42A C42 H42B 111.1 . . ?
N24 C43 C44 123.8(8) . . ?
N24 C43 H43 118.1 . . ?
C44 C43 H43 118.1 . . ?
C43 C44 C45 120.0(7) . . ?
C43 C44 N23 118.5(7) . . ?
C45 C44 N23 121.5(7) . . ?
C44 C45 C46 117.8(7) . . ?
C44 C45 H45 121.1 . . ?
C46 C45 H45 121.1 . . ?
C47 C46 C45 117.6(7) . . ?
C47 C46 C48 121.6(8) . . ?
C45 C46 C48 120.8(8) . . ?
N24 C47 C46 124.3(8) . . ?
N24 C47 C49 113.8(8) . . ?
C46 C47 C49 121.8(8) . . ?
F22 C48 F23 106.8(8) . . ?
F22 C48 F21 107.3(8) . . ?
F23 C48 F21 105.9(7) . . ?
F22 C48 C46 112.7(7) . . ?
F23 C48 C46 111.8(7) . . ?
F21 C48 C46 111.9(8) . . ?
N25 C49 C47 179.0(10) . . ?
N21 C92 H92A 109.5 . . ?
N21 C92 H92B 109.5 . . ?
H92A C92 H92B 109.5 . . ?
N21 C92 H92C 109.5 . . ?
H92A C92 H92C 109.5 . . ?
H92B C92 H92C 109.5 . . ?
C50 N31 C93 120.5(7) . . ?
C50 N31 H31 121(6) . . ?
C93 N31 H31 116(6) . . ?
C57 N32 C54 124.0(6) . . ?
C57 N32 C59 112.9(6) . . ?
C54 N32 C59 121.6(6) . . ?
C57 N33 C58 111.4(6) . . ?
C57 N33 C64 124.1(6) . . ?
C58 N33 C64 123.9(6) . . ?
C63 N34 C67 116.8(7) . . ?
O31 C50 N31 123.5(8) . . ?
O31 C50 C51 119.8(8) . . ?
N31 C50 C51 116.7(7) . . ?
C52 C51 C56 116.6(7) . . ?
C52 C51 C50 119.8(7) . . ?
C56 C51 C50 123.5(8) . . ?
F3A C52 C53 122.6(9) . . ?
F3A C52 C51 114.3(8) . . ?
C53 C52 C51 123.0(7) . . ?
C53 C52 H52 118.5 . . ?
C51 C52 H52 118.5 . . ?
C52 C53 C54 118.1(8) . . ?
C52 C53 H53 121.0 . . ?
C54 C53 H53 121.0 . . ?
C55 C54 C53 121.9(7) . . ?
C55 C54 N32 120.1(7) . . ?
C53 C54 N32 117.8(7) . . ?
C54 C55 C56 118.5(8) . . ?
C54 C55 H55 120.7 . . ?
C56 C55 H55 120.7 . . ?
F3B C56 C51 117.9(9) . . ?
F3B C56 C55 120.3(9) . . ?
C51 C56 C55 121.8(8) . . ?
C51 C56 H56 119.1 . . ?
C55 C56 H56 119.1 . . ?
N32 C57 N33 107.4(6) . . ?
N32 C57 S3 128.1(6) . . ?
N33 C57 S3 124.5(6) . . ?
O32 C58 N33 124.5(7) . . ?
O32 C58 C59 129.4(7) . . ?
N33 C58 C59 106.1(6) . . ?
N32 C59 C58 101.9(6) . . ?
N32 C59 C62 120.0(7) . . ?
C58 C59 C62 112.3(6) . . ?
N32 C59 C60 120.0(6) . . ?
C58 C59 C60 114.2(7) . . ?
C62 C59 C60 89.0(6) . . ?
C59 C60 C61 88.7(6) . . ?
C59 C60 H60A 113.9 . . ?
C61 C60 H60A 113.9 . . ?
C59 C60 H60B 113.9 . . ?
C61 C60 H60B 113.9 . . ?
H60A C60 H60B 111.1 . . ?
C62 C61 C60 87.3(6) . . ?
C62 C61 H61A 114.1 . . ?
C60 C61 H61A 114.1 . . ?
C62 C61 H61B 114.1 . . ?
C60 C61 H61B 114.1 . . ?
H61A C61 H61B 111.3 . . ?
C59 C62 C61 90.1(6) . . ?
C59 C62 H62A 113.6 . . ?
C61 C62 H62A 113.6 . . ?
C59 C62 H62B 113.6 . . ?
C61 C62 H62B 113.6 . . ?
H62A C62 H62B 110.9 . . ?
N34 C63 C64 121.7(7) . . ?
N34 C63 H63 119.2 . . ?
C64 C63 H63 119.2 . . ?
C65 C64 C63 120.5(7) . . ?
C65 C64 N33 120.2(7) . . ?
C63 C64 N33 119.3(7) . . ?
C64 C65 C66 119.3(7) . . ?
C64 C65 H65 120.4 . . ?
C66 C65 H65 120.4 . . ?
C65 C66 C67 117.1(7) . . ?
C65 C66 C68 122.0(7) . . ?
C67 C66 C68 120.9(7) . . ?
N34 C67 C66 124.6(7) . . ?
N34 C67 C69 114.3(7) . . ?
C66 C67 C69 121.0(7) . . ?
F33 C68 F31 107.9(7) . . ?
F33 C68 F32 107.0(7) . . ?
F31 C68 F32 107.0(7) . . ?
F33 C68 C66 111.5(7) . . ?
F31 C68 C66 111.8(7) . . ?
F32 C68 C66 111.4(7) . . ?
N35 C69 C67 178.1(8) . . ?
N31 C93 H93A 109.5 . . ?
N31 C93 H93B 109.5 . . ?
H93A C93 H93B 109.5 . . ?
N31 C93 H93C 109.5 . . ?
H93A C93 H93C 109.5 . . ?
H93B C93 H93C 109.5 . . ?
C70 N41 C94 122.4(7) . . ?
C70 N41 H41 126(6) . . ?
C94 N41 H41 106(6) . . ?
C77 N42 C74 124.2(6) . . ?
C77 N42 C79 112.2(6) . . ?
C74 N42 C79 122.6(6) . . ?
C77 N43 C78 111.2(7) . . ?
C77 N43 C84 123.6(6) . . ?
C78 N43 C84 124.0(6) . . ?
C83 N44 C87 116.7(8) . . ?
O41 C70 N41 122.7(8) . . ?
O41 C70 C71 119.6(7) . . ?
N41 C70 C71 117.7(7) . . ?
C72 C71 C76 117.2(8) . . ?
C72 C71 C70 120.5(7) . . ?
C76 C71 C70 122.1(8) . . ?
F4A C72 C73 121.9(8) . . ?
F4A C72 C71 114.7(8) . . ?
C73 C72 C71 122.9(8) . . ?
C73 C72 H72 118.6 . . ?
C71 C72 H72 118.6 . . ?
C72 C73 C74 118.7(8) . . ?
C72 C73 H73 120.6 . . ?
C74 C73 H73 120.6 . . ?
C73 C74 C75 121.1(7) . . ?
C73 C74 N42 118.9(7) . . ?
C75 C74 N42 119.9(7) . . ?
C74 C75 C76 118.8(8) . . ?
C74 C75 H75 120.6 . . ?
C76 C75 H75 120.6 . . ?
F4B C76 C75 118.9(9) . . ?
F4B C76 C71 119.5(9) . . ?
C75 C76 C71 121.3(8) . . ?
C75 C76 H76 119.4 . . ?
C71 C76 H76 119.4 . . ?
N42 C77 N43 107.6(6) . . ?
N42 C77 S4 127.2(6) . . ?
N43 C77 S4 125.2(6) . . ?
O42 C78 N43 124.7(8) . . ?
O42 C78 C79 128.3(7) . . ?
N43 C78 C79 106.9(7) . . ?
N42 C79 C78 101.7(6) . . ?
N42 C79 C80 118.4(6) . . ?
C78 C79 C80 116.3(7) . . ?
N42 C79 C82 116.9(7) . . ?
C78 C79 C82 114.9(7) . . ?
C80 C79 C82 89.5(6) . . ?
C81B C80 C79 90.5(7) . . ?
C79 C80 C81A 85.5(9) . . ?
C81B C80 H80C 113.6 . . ?
C79 C80 H80C 113.6 . . ?
C81B C80 H80D 113.6 . . ?
C79 C80 H80D 113.6 . . ?
H80C C80 H80D 110.8 . . ?
C79 C80 H80A 114.4 . . ?
C81A C80 H80A 114.4 . . ?
C79 C80 H80B 114.4 . . ?
C81A C80 H80B 114.4 . . ?
H80A C80 H80B 111.5 . . ?
C82 C81A C80 92.0(11) . . ?
C82 C81A H81A 113.3 . . ?
C80 C81A H81A 113.3 . . ?
C82 C81A H81B 113.3 . . ?
C80 C81A H81B 113.3 . . ?
H81A C81A H81B 110.6 . . ?
C80 C81B C82 89.1(8) . . ?
C80 C81B H81C 113.8 . . ?
C82 C81B H81C 113.8 . . ?
C80 C81B H81D 113.8 . . ?
C82 C81B H81D 113.8 . . ?
H81C C81B H81D 111.0 . . ?
C81A C82 C79 88.0(9) . . ?
C79 C82 C81B 88.2(7) . . ?
C79 C82 H82C 114.0 . . ?
C81B C82 H82C 114.0 . . ?
C79 C82 H82D 114.0 . . ?
C81B C82 H82D 114.0 . . ?
H82C C82 H82D 111.2 . . ?
C81A C82 H82A 114.0 . . ?
C79 C82 H82A 114.0 . . ?
C81A C82 H82B 114.0 . . ?
C79 C82 H82B 114.0 . . ?
H82A C82 H82B 111.2 . . ?
N44 C83 C84 124.7(9) . . ?
N44 C83 H83 117.7 . . ?
C84 C83 H83 117.7 . . ?
C85 C84 C83 116.8(8) . . ?
C85 C84 N43 122.2(7) . . ?
C83 C84 N43 120.9(8) . . ?
C86 C85 C84 120.1(8) . . ?
C86 C85 H85 119.9 . . ?
C84 C85 H85 119.9 . . ?
C85 C86 C87 117.9(8) . . ?
C85 C86 C88 121.8(8) . . ?
C87 C86 C88 120.3(8) . . ?
N44 C87 C86 123.8(8) . . ?
N44 C87 C89 115.0(9) . . ?
C86 C87 C89 121.1(9) . . ?
F43 C88 F42 107.2(8) . . ?
F43 C88 F41 107.8(9) . . ?
F42 C88 F41 106.0(9) . . ?
F43 C88 C86 112.5(9) . . ?
F42 C88 C86 111.5(9) . . ?
F41 C88 C86 111.5(8) . . ?
N45 C89 C87 179.8(16) . . ?
N41 C94 H94A 109.5 . . ?
N41 C94 H94B 109.5 . . ?
H94A C94 H94B 109.5 . . ?
N41 C94 H94C 109.5 . . ?
H94A C94 H94C 109.5 . . ?
H94B C94 H94C 109.5 . . ?
C1 N1 C2 120.8(9) . . ?
C1 N1 C3 122.3(10) . . ?
C2 N1 C3 116.7(10) . . ?
O1 C1 N1 126.2(10) . . ?
O1 C1 H1 116.9 . . ?
N1 C1 H1 116.9 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 N2 C6 122.5(8) . . ?
C4 N2 C5 120.1(8) . . ?
C6 N2 C5 117.4(8) . . ?
O2 C4 N2 127.2(9) . . ?
O2 C4 H4 116.4 . . ?
N2 C4 H4 116.4 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
C91 N11 C10 O11 4.9(13) . . . . ?
C91 N11 C10 C11 -176.4(7) . . . . ?
O11 C10 C11 C12 -136.1(8) . . . . ?
N11 C10 C11 C12 45.2(10) . . . . ?
O11 C10 C11 C16 40.5(11) . . . . ?
N11 C10 C11 C16 -138.3(8) . . . . ?
C16 C11 C12 F1A -168.3(9) . . . . ?
C10 C11 C12 F1A 8.4(13) . . . . ?
C16 C11 C12 C13 1.0(11) . . . . ?
C10 C11 C12 C13 177.7(7) . . . . ?
F1A C12 C13 C14 170.3(8) . . . . ?
C11 C12 C13 C14 0.2(12) . . . . ?
C12 C13 C14 C15 0.5(11) . . . . ?
C12 C13 C14 N12 177.5(7) . . . . ?
C17 N12 C14 C13 87.3(9) . . . . ?
C19 N12 C14 C13 -91.8(9) . . . . ?
C17 N12 C14 C15 -95.7(9) . . . . ?
C19 N12 C14 C15 85.3(9) . . . . ?
C13 C14 C15 C16 -2.5(11) . . . . ?
N12 C14 C15 C16 -179.5(6) . . . . ?
C14 C15 C16 F1B -177.5(7) . . . . ?
C14 C15 C16 C11 3.9(11) . . . . ?
C12 C11 C16 F1B 178.2(7) . . . . ?
C10 C11 C16 F1B 1.5(11) . . . . ?
C12 C11 C16 C15 -3.1(11) . . . . ?
C10 C11 C16 C15 -179.9(7) . . . . ?
C14 N12 C17 N13 -176.8(6) . . . . ?
C19 N12 C17 N13 2.3(8) . . . . ?
C14 N12 C17 S1 4.6(10) . . . . ?
C19 N12 C17 S1 -176.3(5) . . . . ?
C18 N13 C17 N12 2.9(8) . . . . ?
C24 N13 C17 N12 -177.3(6) . . . . ?
C18 N13 C17 S1 -178.5(6) . . . . ?
C24 N13 C17 S1 1.3(10) . . . . ?
C17 N13 C18 O12 174.5(7) . . . . ?
C24 N13 C18 O12 -5.3(12) . . . . ?
C17 N13 C18 C19 -6.5(8) . . . . ?
C24 N13 C18 C19 173.6(6) . . . . ?
C17 N12 C19 C18 -5.9(8) . . . . ?
C14 N12 C19 C18 173.2(6) . . . . ?
C17 N12 C19 C22 120.2(7) . . . . ?
C14 N12 C19 C22 -60.7(10) . . . . ?
C17 N12 C19 C20 -132.4(7) . . . . ?
C14 N12 C19 C20 46.7(10) . . . . ?
O12 C18 C19 N12 -173.9(8) . . . . ?
N13 C18 C19 N12 7.2(7) . . . . ?
O12 C18 C19 C22 56.7(11) . . . . ?
N13 C18 C19 C22 -122.2(7) . . . . ?
O12 C18 C19 C20 -42.4(11) . . . . ?
N13 C18 C19 C20 138.7(6) . . . . ?
N12 C19 C20 C21 -142.3(7) . . . . ?
C18 C19 C20 C21 96.4(7) . . . . ?
C22 C19 C20 C21 -19.0(6) . . . . ?
C19 C20 C21 C22 18.9(6) . . . . ?
N12 C19 C22 C21 143.9(7) . . . . ?
C18 C19 C22 C21 -95.9(7) . . . . ?
C20 C19 C22 C21 18.8(6) . . . . ?
C20 C21 C22 C19 -19.0(6) . . . . ?
C27 N14 C23 C24 1.4(11) . . . . ?
N14 C23 C24 C25 1.7(11) . . . . ?
N14 C23 C24 N13 -178.3(7) . . . . ?
C18 N13 C24 C25 129.7(8) . . . . ?
C17 N13 C24 C25 -50.1(10) . . . . ?
C18 N13 C24 C23 -50.2(10) . . . . ?
C17 N13 C24 C23 130.0(7) . . . . ?
C23 C24 C25 C26 -1.7(11) . . . . ?
N13 C24 C25 C26 178.3(6) . . . . ?
C24 C25 C26 C27 -1.2(10) . . . . ?
C24 C25 C26 C28 -176.9(7) . . . . ?
C23 N14 C27 C26 -4.5(11) . . . . ?
C23 N14 C27 C29 176.0(7) . . . . ?
C25 C26 C27 N14 4.5(11) . . . . ?
C28 C26 C27 N14 -179.7(7) . . . . ?
C25 C26 C27 C29 -176.1(7) . . . . ?
C28 C26 C27 C29 -0.3(11) . . . . ?
C25 C26 C28 F11 117.6(8) . . . . ?
C27 C26 C28 F11 -58.0(10) . . . . ?
C25 C26 C28 F13 -3.0(10) . . . . ?
C27 C26 C28 F13 -178.7(7) . . . . ?
C25 C26 C28 F12 -123.1(8) . . . . ?
C27 C26 C28 F12 61.2(10) . . . . ?
C92 N21 C30 O21 -3.3(13) . . . . ?
C92 N21 C30 C31 175.7(8) . . . . ?
O21 C30 C31 C36 -43.7(10) . . . . ?
N21 C30 C31 C36 137.3(8) . . . . ?
O21 C30 C31 C32 133.0(8) . . . . ?
N21 C30 C31 C32 -46.0(10) . . . . ?
C36 C31 C32 F2A 173.5(7) . . . . ?
C30 C31 C32 F2A -3.3(11) . . . . ?
C36 C31 C32 C33 -0.1(11) . . . . ?
C30 C31 C32 C33 -176.9(7) . . . . ?
F2A C32 C33 C34 -173.7(7) . . . . ?
C31 C32 C33 C34 0.0(11) . . . . ?
C32 C33 C34 C35 -0.8(11) . . . . ?
C32 C33 C34 N22 -179.2(6) . . . . ?
C37 N22 C34 C35 101.6(8) . . . . ?
C39 N22 C34 C35 -81.0(9) . . . . ?
C37 N22 C34 C33 -79.9(8) . . . . ?
C39 N22 C34 C33 97.5(8) . . . . ?
C33 C34 C35 C36 1.4(11) . . . . ?
N22 C34 C35 C36 179.9(6) . . . . ?
C34 C35 C36 F2B 177.0(8) . . . . ?
C34 C35 C36 C31 -1.5(11) . . . . ?
C32 C31 C36 F2B -177.6(8) . . . . ?
C30 C31 C36 F2B -0.8(11) . . . . ?
C32 C31 C36 C35 0.8(11) . . . . ?
C30 C31 C36 C35 177.6(7) . . . . ?
C34 N22 C37 N23 -179.9(6) . . . . ?
C39 N22 C37 N23 2.5(8) . . . . ?
C34 N22 C37 S2 -1.8(10) . . . . ?
C39 N22 C37 S2 -179.4(5) . . . . ?
C38 N23 C37 N22 -4.1(8) . . . . ?
C44 N23 C37 N22 177.5(6) . . . . ?
C38 N23 C37 S2 177.7(6) . . . . ?
C44 N23 C37 S2 -0.6(10) . . . . ?
C37 N23 C38 O22 -176.1(8) . . . . ?
C44 N23 C38 O22 2.3(12) . . . . ?
C37 N23 C38 C39 4.1(8) . . . . ?
C44 N23 C38 C39 -177.5(6) . . . . ?
C37 N22 C39 C38 -0.1(8) . . . . ?
C34 N22 C39 C38 -177.6(6) . . . . ?
C37 N22 C39 C42 -127.1(7) . . . . ?
C34 N22 C39 C42 55.4(9) . . . . ?
C37 N22 C39 C40 124.0(7) . . . . ?
C34 N22 C39 C40 -53.6(9) . . . . ?
O22 C38 C39 N22 177.8(9) . . . . ?
N23 C38 C39 N22 -2.4(7) . . . . ?
O22 C38 C39 C42 -50.3(11) . . . . ?
N23 C38 C39 C42 129.5(7) . . . . ?
O22 C38 C39 C40 48.5(12) . . . . ?
N23 C38 C39 C40 -131.7(7) . . . . ?
N22 C39 C40 C41 144.1(7) . . . . ?
C38 C39 C40 C41 -96.6(7) . . . . ?
C42 C39 C40 C41 18.2(6) . . . . ?
C39 C40 C41 C42 -18.0(6) . . . . ?
N22 C39 C42 C41 -143.1(7) . . . . ?
C38 C39 C42 C41 95.2(7) . . . . ?
C40 C39 C42 C41 -18.2(6) . . . . ?
C40 C41 C42 C39 18.3(6) . . . . ?
C47 N24 C43 C44 2.5(12) . . . . ?
N24 C43 C44 C45 -3.5(12) . . . . ?
N24 C43 C44 N23 177.8(7) . . . . ?
C37 N23 C44 C43 -127.1(8) . . . . ?
C38 N23 C44 C43 54.7(10) . . . . ?
C37 N23 C44 C45 54.2(10) . . . . ?
C38 N23 C44 C45 -123.9(8) . . . . ?
C43 C44 C45 C46 2.0(11) . . . . ?
N23 C44 C45 C46 -179.4(7) . . . . ?
C44 C45 C46 C47 0.2(11) . . . . ?
C44 C45 C46 C48 178.8(8) . . . . ?
C43 N24 C47 C46 0.0(12) . . . . ?
C43 N24 C47 C49 -177.8(7) . . . . ?
C45 C46 C47 N24 -1.3(12) . . . . ?
C48 C46 C47 N24 -179.8(8) . . . . ?
C45 C46 C47 C49 176.3(7) . . . . ?
C48 C46 C47 C49 -2.3(12) . . . . ?
C47 C46 C48 F22 178.9(8) . . . . ?
C45 C46 C48 F22 0.4(12) . . . . ?
C47 C46 C48 F23 58.5(11) . . . . ?
C45 C46 C48 F23 -120.0(9) . . . . ?
C47 C46 C48 F21 -60.1(11) . . . . ?
C45 C46 C48 F21 121.4(9) . . . . ?
C93 N31 C50 O31 2.3(14) . . . . ?
C93 N31 C50 C51 -177.9(7) . . . . ?
O31 C50 C51 C52 44.4(12) . . . . ?
N31 C50 C51 C52 -135.4(8) . . . . ?
O31 C50 C51 C56 -132.3(10) . . . . ?
N31 C50 C51 C56 47.9(11) . . . . ?
C56 C51 C52 F3A -178.3(8) . . . . ?
C50 C51 C52 F3A 4.7(12) . . . . ?
C56 C51 C52 C53 -0.3(12) . . . . ?
C50 C51 C52 C53 -177.3(7) . . . . ?
F3A C52 C53 C54 -179.7(8) . . . . ?
C51 C52 C53 C54 2.5(12) . . . . ?
C52 C53 C54 C55 -3.5(12) . . . . ?
C52 C53 C54 N32 -179.1(7) . . . . ?
C57 N32 C54 C55 106.6(9) . . . . ?
C59 N32 C54 C55 -88.4(9) . . . . ?
C57 N32 C54 C53 -77.7(10) . . . . ?
C59 N32 C54 C53 87.3(9) . . . . ?
C53 C54 C55 C56 2.4(12) . . . . ?
N32 C54 C55 C56 177.8(7) . . . . ?
C52 C51 C56 F3B -178.8(10) . . . . ?
C50 C51 C56 F3B -2.0(14) . . . . ?
C52 C51 C56 C55 -0.9(12) . . . . ?
C50 C51 C56 C55 175.9(7) . . . . ?
C54 C55 C56 F3B 177.8(11) . . . . ?
C54 C55 C56 C51 -0.1(12) . . . . ?
C54 N32 C57 N33 166.6(7) . . . . ?
C59 N32 C57 N33 0.4(9) . . . . ?
C54 N32 C57 S3 -12.7(12) . . . . ?
C59 N32 C57 S3 -178.9(6) . . . . ?
C58 N33 C57 N32 -4.1(9) . . . . ?
C64 N33 C57 N32 -175.4(7) . . . . ?
C58 N33 C57 S3 175.2(6) . . . . ?
C64 N33 C57 S3 4.0(11) . . . . ?
C57 N33 C58 O32 -174.9(7) . . . . ?
C64 N33 C58 O32 -3.7(12) . . . . ?
C57 N33 C58 C59 6.0(8) . . . . ?
C64 N33 C58 C59 177.3(7) . . . . ?
C57 N32 C59 C58 3.1(8) . . . . ?
C54 N32 C59 C58 -163.5(7) . . . . ?
C57 N32 C59 C62 -121.7(8) . . . . ?
C54 N32 C59 C62 71.8(9) . . . . ?
C57 N32 C59 C60 130.4(8) . . . . ?
C54 N32 C59 C60 -36.2(10) . . . . ?
O32 C58 C59 N32 175.7(8) . . . . ?
N33 C58 C59 N32 -5.3(8) . . . . ?
O32 C58 C59 C62 -54.6(11) . . . . ?
N33 C58 C59 C62 124.4(7) . . . . ?
O32 C58 C59 C60 44.8(11) . . . . ?
N33 C58 C59 C60 -136.2(6) . . . . ?
N32 C59 C60 C61 141.2(7) . . . . ?
C58 C59 C60 C61 -97.4(7) . . . . ?
C62 C59 C60 C61 16.7(6) . . . . ?
C59 C60 C61 C62 -16.5(6) . . . . ?
N32 C59 C62 C61 -141.4(7) . . . . ?
C58 C59 C62 C61 98.9(7) . . . . ?
C60 C59 C62 C61 -17.0(6) . . . . ?
C60 C61 C62 C59 16.7(6) . . . . ?
C67 N34 C63 C64 -0.7(10) . . . . ?
N34 C63 C64 C65 1.5(11) . . . . ?
N34 C63 C64 N33 -179.0(6) . . . . ?
C57 N33 C64 C65 107.7(9) . . . . ?
C58 N33 C64 C65 -62.4(10) . . . . ?
C57 N33 C64 C63 -71.8(9) . . . . ?
C58 N33 C64 C63 118.1(8) . . . . ?
C63 C64 C65 C66 -0.6(11) . . . . ?
N33 C64 C65 C66 179.9(6) . . . . ?
C64 C65 C66 C67 -1.0(11) . . . . ?
C64 C65 C66 C68 176.2(7) . . . . ?
C63 N34 C67 C66 -1.0(11) . . . . ?
C63 N34 C67 C69 178.5(6) . . . . ?
C65 C66 C67 N34 1.9(11) . . . . ?
C68 C66 C67 N34 -175.4(7) . . . . ?
C65 C66 C67 C69 -177.6(7) . . . . ?
C68 C66 C67 C69 5.2(11) . . . . ?
C65 C66 C68 F33 -122.2(8) . . . . ?
C67 C66 C68 F33 54.9(10) . . . . ?
C65 C66 C68 F31 -1.3(11) . . . . ?
C67 C66 C68 F31 175.8(7) . . . . ?
C65 C66 C68 F32 118.3(8) . . . . ?
C67 C66 C68 F32 -64.5(9) . . . . ?
C94 N41 C70 O41 -0.4(13) . . . . ?
C94 N41 C70 C71 179.0(7) . . . . ?
O41 C70 C71 C72 -47.9(11) . . . . ?
N41 C70 C71 C72 132.7(8) . . . . ?
O41 C70 C71 C76 127.3(8) . . . . ?
N41 C70 C71 C76 -52.1(10) . . . . ?
C76 C71 C72 F4A 171.1(7) . . . . ?
C70 C71 C72 F4A -13.5(11) . . . . ?
C76 C71 C72 C73 -0.7(11) . . . . ?
C70 C71 C72 C73 174.7(7) . . . . ?
F4A C72 C73 C74 -171.6(8) . . . . ?
C71 C72 C73 C74 -0.3(12) . . . . ?
C72 C73 C74 C75 1.5(11) . . . . ?
C72 C73 C74 N42 177.8(7) . . . . ?
C77 N42 C74 C73 82.7(10) . . . . ?
C79 N42 C74 C73 -84.7(9) . . . . ?
C77 N42 C74 C75 -100.9(9) . . . . ?
C79 N42 C74 C75 91.6(9) . . . . ?
C73 C74 C75 C76 -1.5(11) . . . . ?
N42 C74 C75 C76 -177.7(7) . . . . ?
C74 C75 C76 F4B 173.5(10) . . . . ?
C74 C75 C76 C71 0.4(12) . . . . ?
C72 C71 C76 F4B -172.4(10) . . . . ?
C70 C71 C76 F4B 12.3(13) . . . . ?
C72 C71 C76 C75 0.7(11) . . . . ?
C70 C71 C76 C75 -174.6(7) . . . . ?
C74 N42 C77 N43 -168.2(7) . . . . ?
C79 N42 C77 N43 0.4(9) . . . . ?
C74 N42 C77 S4 14.0(12) . . . . ?
C79 N42 C77 S4 -177.4(6) . . . . ?
C78 N43 C77 N42 4.2(9) . . . . ?
C84 N43 C77 N42 172.0(7) . . . . ?
C78 N43 C77 S4 -177.9(6) . . . . ?
C84 N43 C77 S4 -10.2(11) . . . . ?
C77 N43 C78 O42 175.2(8) . . . . ?
C84 N43 C78 O42 7.5(13) . . . . ?
C77 N43 C78 C79 -7.0(9) . . . . ?
C84 N43 C78 C79 -174.6(7) . . . . ?
C77 N42 C79 C78 -4.3(8) . . . . ?
C74 N42 C79 C78 164.5(7) . . . . ?
C77 N42 C79 C80 -133.1(8) . . . . ?
C74 N42 C79 C80 35.7(11) . . . . ?
C77 N42 C79 C82 121.7(8) . . . . ?
C74 N42 C79 C82 -69.6(9) . . . . ?
O42 C78 C79 N42 -175.7(8) . . . . ?
N43 C78 C79 N42 6.5(8) . . . . ?
O42 C78 C79 C80 -45.6(12) . . . . ?
N43 C78 C79 C80 136.7(7) . . . . ?
O42 C78 C79 C82 57.1(11) . . . . ?
N43 C78 C79 C82 -120.7(7) . . . . ?
N42 C79 C80 C81B -133.4(9) . . . . ?
C78 C79 C80 C81B 104.9(9) . . . . ?
C82 C79 C80 C81B -12.8(9) . . . . ?
N42 C79 C80 C81A -104.4(13) . . . . ?
C78 C79 C80 C81A 134.0(12) . . . . ?
C82 C79 C80 C81A 16.2(12) . . . . ?
C79 C80 C81A C82 -17.0(12) . . . . ?
C79 C80 C81B C82 12.6(8) . . . . ?
C80 C81A C82 C79 17.0(12) . . . . ?
N42 C79 C82 C81A 104.9(13) . . . . ?
C78 C79 C82 C81A -136.0(13) . . . . ?
C80 C79 C82 C81A -17.0(13) . . . . ?
N42 C79 C82 C81B 134.3(9) . . . . ?
C78 C79 C82 C81B -106.7(9) . . . . ?
C80 C79 C82 C81B 12.3(8) . . . . ?
C80 C81B C82 C79 -12.6(8) . . . . ?
C87 N44 C83 C84 -1.2(16) . . . . ?
N44 C83 C84 C85 -0.5(14) . . . . ?
N44 C83 C84 N43 177.5(9) . . . . ?
C77 N43 C84 C85 -80.3(10) . . . . ?
C78 N43 C84 C85 85.9(10) . . . . ?
C77 N43 C84 C83 101.8(10) . . . . ?
C78 N43 C84 C83 -92.0(10) . . . . ?
C83 C84 C85 C86 2.1(12) . . . . ?
N43 C84 C85 C86 -175.9(7) . . . . ?
C84 C85 C86 C87 -1.9(12) . . . . ?
C84 C85 C86 C88 178.7(8) . . . . ?
C83 N44 C87 C86 1.3(15) . . . . ?
C83 N44 C87 C89 -178.9(9) . . . . ?
C85 C86 C87 N44 0.2(14) . . . . ?
C88 C86 C87 N44 179.5(9) . . . . ?
C85 C86 C87 C89 -179.6(8) . . . . ?
C88 C86 C87 C89 -0.2(13) . . . . ?
C85 C86 C88 F43 115.2(10) . . . . ?
C87 C86 C88 F43 -64.1(12) . . . . ?
C85 C86 C88 F42 -124.3(10) . . . . ?
C87 C86 C88 F42 56.4(13) . . . . ?
C85 C86 C88 F41 -6.1(13) . . . . ?
C87 C86 C88 F41 174.6(8) . . . . ?
C2 N1 C1 O1 -0.4(17) . . . . ?
C3 N1 C1 O1 176.1(11) . . . . ?
C6 N2 C4 O2 -179.5(9) . . . . ?
C5 N2 C4 O2 -1.3(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
N11 H11 O31 0.85(5) 1.96(6) 2.756(9) 156(9) .
N21 H21 O41 0.85(5) 1.97(5) 2.811(9) 169(9) .
N31 H31 O21 0.85(5) 2.08(5) 2.936(9) 175(9) 1_445
N41 H41 O11 0.84(5) 2.07(5) 2.883(8) 163(8) 1_655

_refine_diff_density_max         0.674
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.090

####################################################################### 
# 
# 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_KA1156_0m_APA-DOX-2-1
_database_code_depnum_ccdc_archive 'CCDC 2152152'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-02-15 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            Apalutamide-1,4-dioxane-2:1
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C21 H15 F4 N5 O2 S), C4 H8 O2'
_chemical_formula_sum            'C46 H38 F8 N10 O6 S2'
_chemical_formula_weight         1042.98

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   41.7833(6)
_cell_length_b                   13.6224(2)
_cell_length_c                   17.4061(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.9090(7)
_cell_angle_gamma                90
_cell_volume                     9254.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9934
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      26.36

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             4288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.209
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5793
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS 2014/5'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36635
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.165
_diffrn_reflns_theta_max         26.394
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9440
_reflns_number_gt                6534
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0679P)²+56.7028P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         9440
_refine_ls_number_parameters     669
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0832
_refine_ls_wR_factor_ref         0.2010
_refine_ls_wR_factor_gt          0.1806
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
C1A C 0.60319(10) 0.6262(3) 0.1293(2) 0.0209(8) Uani 1 1 d . . . . .
C2A C 0.57380(10) 0.6299(3) 0.1473(2) 0.0230(9) Uani 1 1 d . . . . .
H2A H 0.568057 0.686247 0.169714 0.028 Uiso 1 1 calc R U . . .
C3A C 0.55290(10) 0.5478(3) 0.1313(2) 0.0237(9) Uani 1 1 d . . . . .
C4A C 0.56326(11) 0.4655(3) 0.0983(2) 0.0265(9) Uani 1 1 d . . . . .
C5A C 0.61155(11) 0.5416(3) 0.0957(3) 0.0283(9) Uani 1 1 d . . . . .
H5A H 0.631577 0.540670 0.083929 0.034 Uiso 1 1 calc R U . . .
C6A C 0.64459(11) 0.7472(3) 0.2192(2) 0.0243(9) Uani 1 1 d . . . . .
C7A C 0.64598(11) 0.8609(3) 0.1199(2) 0.0227(9) Uani 1 1 d . . . . .
C8A C 0.62430(12) 0.7739(3) 0.0793(2) 0.0287(10) Uani 1 1 d . . . . .
C9A C 0.52008(11) 0.5465(3) 0.1486(3) 0.0309(10) Uani 1 1 d . . . . .
C10A C 0.54286(13) 0.3760(3) 0.0815(3) 0.0368(11) Uani 1 1 d . . . . .
C11A C 0.67821(10) 0.8940(3) 0.2724(2) 0.0211(8) Uani 1 1 d . . . . .
C12A C 0.66514(10) 0.9743(3) 0.2994(2) 0.0212(8) Uani 1 1 d . . . . .
H12A H 0.642065 0.990683 0.276013 0.025 Uiso 1 1 calc R U . . .
C13A C 0.68735(10) 1.0297(3) 0.3623(2) 0.0217(8) Uani 1 1 d . . . . .
C14A C 0.72178(10) 1.0075(3) 0.3992(2) 0.0191(8) Uani 1 1 d . . . . .
C15A C 0.73431(11) 0.9271(3) 0.3698(2) 0.0272(9) Uani 1 1 d . . . . .
H15A H 0.757390 0.910849 0.393260 0.033 Uiso 1 1 calc R U . . .
C16A C 0.71281(11) 0.8706(3) 0.3057(2) 0.0287(10) Uani 1 1 d . . . . .
H16A H 0.721466 0.817856 0.285313 0.034 Uiso 1 1 calc R U . . .
C17A C 0.62915(11) 0.9608(3) 0.0865(2) 0.0286(9) Uani 1 1 d . . . . .
H17A H 0.604649 0.956997 0.056655 0.034 Uiso 1 1 calc R U . . .
H17B H 0.634641 1.012480 0.127505 0.034 Uiso 1 1 calc R U . . .
C18A C 0.67431(13) 0.8856(3) 0.0854(3) 0.0374(11) Uani 1 1 d . . . . .
H18A H 0.695006 0.912013 0.126032 0.045 Uiso 1 1 calc R U . . .
H18B H 0.679581 0.832297 0.054902 0.045 Uiso 1 1 calc R U . . .
C19A C 0.65065(13) 0.9642(3) 0.0306(3) 0.0369(11) Uani 1 1 d . . . . .
H19A H 0.638344 0.942512 -0.025311 0.044 Uiso 1 1 calc R U . . .
H19B H 0.661813 1.026744 0.031249 0.044 Uiso 1 1 calc R U . . .
C20A C 0.74408(10) 1.0681(3) 0.4706(2) 0.0192(8) Uani 1 1 d . . . . .
C21A C 0.79006(13) 1.1885(3) 0.5179(3) 0.0348(11) Uani 1 1 d . . . . .
H21A H 0.785229 1.256297 0.503227 0.052 Uiso 1 1 calc R U . . .
H21B H 0.813076 1.173618 0.522043 0.052 Uiso 1 1 calc R U . . .
H21C H 0.787611 1.176369 0.569843 0.052 Uiso 1 1 calc R U . . .
S1A S 0.65448(4) 0.68837(9) 0.30389(7) 0.0434(3) Uani 1 1 d . . . . .
F1A F 0.51285(7) 0.6335(2) 0.17117(17) 0.0444(7) Uani 1 1 d . . . . .
F2A F 0.52160(7) 0.4818(2) 0.20714(15) 0.0403(7) Uani 1 1 d . . . . .
F3A F 0.49338(6) 0.5192(2) 0.08169(15) 0.0437(7) Uani 1 1 d . . . . .
F4A F 0.67501(6) 1.11010(17) 0.38779(14) 0.0324(6) Uani 1 1 d . . . . .
O1A O 0.60933(10) 0.7595(2) 0.00723(18) 0.0478(10) Uani 1 1 d . . . . .
O2A O 0.74063(8) 1.0623(2) 0.53787(16) 0.0269(7) Uani 1 1 d . . . . .
N1A N 0.59169(10) 0.4617(3) 0.0798(2) 0.0327(9) Uani 1 1 d . . . . .
N2A N 0.62493(8) 0.7101(2) 0.14194(18) 0.0211(7) Uani 1 1 d . . . . .
N3A N 0.65550(8) 0.8359(2) 0.20680(19) 0.0218(7) Uani 1 1 d . . . . .
N4A N 0.52672(13) 0.3067(3) 0.0685(3) 0.0554(13) Uani 1 1 d . . . . .
N5A N 0.76613(9) 1.1266(2) 0.45486(19) 0.0239(8) Uani 1 1 d D . . . .
H5NA H 0.7679(10) 1.126(3) 0.4090(15) 0.016(10) Uiso 1 1 d D . . . .
C1B C 0.60959(11) 0.4783(3) 0.3690(3) 0.0323(10) Uani 1 1 d . . . . .
C2B C 0.58409(11) 0.4159(3) 0.3682(2) 0.0323(10) Uani 1 1 d . . . . .
H2B H 0.568657 0.432505 0.393541 0.039 Uiso 1 1 calc R U . . .
C3B C 0.58185(12) 0.3259(3) 0.3279(2) 0.0348(11) Uani 1 1 d . . . . .
C4B C 0.60564(12) 0.3076(4) 0.2890(3) 0.0372(11) Uani 1 1 d . . . . .
C5B C 0.63186(13) 0.4535(4) 0.3299(3) 0.0426(12) Uani 1 1 d . . . . .
H5B H 0.649087 0.497810 0.332055 0.051 Uiso 1 1 calc R U . . .
C6B C 0.64471(10) 0.6012(3) 0.4706(2) 0.0239(9) Uani 1 1 d . . . . .
C7B C 0.60831(10) 0.7387(3) 0.4382(2) 0.0278(9) Uani 1 1 d . . . . .
C8B C 0.59062(11) 0.6501(3) 0.3882(3) 0.0322(10) Uani 1 1 d . . . . .
C9B C 0.55532(14) 0.2506(5) 0.3223(3) 0.0497(15) Uani 1 1 d . . . . .
C10B C 0.60499(13) 0.2206(4) 0.2424(3) 0.0428(12) Uani 1 1 d . . . . .
C11B C 0.66973(10) 0.7489(3) 0.5451(2) 0.0199(8) Uani 1 1 d . . . . .
C12B C 0.67133(11) 0.7616(3) 0.6254(2) 0.0255(9) Uani 1 1 d . . . . .
H12 H 0.653863 0.738147 0.641760 0.031 Uiso 1 1 calc R U . . .
C13B C 0.69893(11) 0.8092(3) 0.6803(2) 0.0264(9) Uani 1 1 d . . . . .
H13D H 0.699744 0.817734 0.734004 0.032 Uiso 0.458(7) 1 calc R U P A 2
C14B C 0.72584(10) 0.8453(3) 0.6589(2) 0.0187(8) Uani 1 1 d . . . . .
C15B C 0.72346(10) 0.8305(3) 0.5775(2) 0.0211(8) Uani 1 1 d . . . . .
H15B H 0.741058 0.853082 0.561179 0.025 Uiso 0.542(7) 1 calc R U P A 1
C16B C 0.69603(10) 0.7837(3) 0.5208(2) 0.0216(8) Uani 1 1 d . . . . .
H16 H 0.695010 0.775394 0.466957 0.026 Uiso 1 1 calc R U . . .
C17B C 0.60636(12) 0.8312(3) 0.3847(3) 0.0318(10) Uani 1 1 d . . . . .
H17C H 0.626476 0.872896 0.404804 0.038 Uiso 1 1 calc R U . . .
H17D H 0.600318 0.817340 0.326552 0.038 Uiso 1 1 calc R U . . .
C18B C 0.58718(12) 0.7945(4) 0.4809(3) 0.0373(11) Uani 1 1 d . . . . .
H18C H 0.600902 0.823996 0.532969 0.045 Uiso 1 1 calc R U . . .
H18D H 0.568390 0.756682 0.486155 0.045 Uiso 1 1 calc R U . . .
C19B C 0.57624(13) 0.8671(4) 0.4080(3) 0.0406(12) Uani 1 1 d . . . . .
H19C H 0.553955 0.852891 0.366865 0.049 Uiso 1 1 calc R U . . .
H19D H 0.577932 0.935481 0.424443 0.049 Uiso 1 1 calc R U . . .
C20B C 0.75599(10) 0.8941(3) 0.7216(2) 0.0221(9) Uani 1 1 d . . . . .
C21B C 0.79630(11) 1.0298(3) 0.7515(3) 0.0327(10) Uani 1 1 d . . . . .
H21D H 0.799666 1.087925 0.724142 0.049 Uiso 1 1 calc R U . . .
H21E H 0.816339 0.989121 0.765526 0.049 Uiso 1 1 calc R U . . .
H21F H 0.792361 1.047878 0.800715 0.049 Uiso 1 1 calc R U . . .
S1B S 0.67658(3) 0.53056(9) 0.50905(7) 0.0374(3) Uani 1 1 d . . . . .
F1B F 0.53694(8) 0.2785(3) 0.36923(19) 0.0598(9) Uani 1 1 d . . . . .
F2B F 0.56738(10) 0.1633(2) 0.3460(2) 0.0685(10) Uani 1 1 d . . . . .
F3B F 0.53309(9) 0.2417(3) 0.24547(19) 0.0749(12) Uani 1 1 d . . . . .
F4B F 0.70132(12) 0.8101(4) 0.7607(2) 0.0353(15) Uani 0.542(7) 1 d . . P A 1
F4D F 0.75103(12) 0.8473(3) 0.5550(3) 0.0225(15) Uani 0.458(7) 1 d . . P A 2
O1B O 0.56259(8) 0.6466(3) 0.3353(2) 0.0520(10) Uani 1 1 d . . . . .
O2B O 0.76943(8) 0.8589(2) 0.79143(16) 0.0307(7) Uani 1 1 d . . . . .
N1B N 0.63023(11) 0.3700(3) 0.2892(3) 0.0463(11) Uani 1 1 d . . . . .
N2B N 0.61354(9) 0.5728(3) 0.4112(2) 0.0268(8) Uani 1 1 d . . . . .
N3B N 0.64172(8) 0.6968(2) 0.48728(19) 0.0210(7) Uani 1 1 d . . . . .
N4B N 0.60593(12) 0.1515(3) 0.2047(3) 0.0549(12) Uani 1 1 d . . . . .
N5B N 0.76689(9) 0.9761(3) 0.69738(19) 0.0238(7) Uani 1 1 d D . . . .
H5NB H 0.7579(12) 0.998(4) 0.6496(16) 0.042(14) Uiso 1 1 d D . . . .
C22 C 0.56006(13) -0.0523(4) 0.1719(3) 0.0436(12) Uani 1 1 d . . . . .
H22A H 0.564511 0.004677 0.143775 0.052 Uiso 1 1 calc R U . . .
H22B H 0.577153 -0.053730 0.226954 0.052 Uiso 1 1 calc R U . . .
C23 C 0.53649(12) -0.1383(4) 0.0487(3) 0.0440(12) Uani 1 1 d . . . . .
H23A H 0.537436 -0.198977 0.020476 0.053 Uiso 1 1 calc R U . . .
H23B H 0.540545 -0.084447 0.016881 0.053 Uiso 1 1 calc R U . . .
C24 C 0.50193(12) -0.1275(4) 0.0535(3) 0.0452(13) Uani 1 1 d . . . . .
H24A H 0.484937 -0.124826 -0.001646 0.054 Uiso 1 1 calc R U . . .
H24B H 0.496992 -0.184325 0.081004 0.054 Uiso 1 1 calc R U . . .
C25 C 0.52552(14) -0.0434(4) 0.1770(3) 0.0513(14) Uani 1 1 d . . . . .
H25A H 0.521471 -0.098705 0.207443 0.062 Uiso 1 1 calc R U . . .
H25B H 0.524418 0.016137 0.206621 0.062 Uiso 1 1 calc R U . . .
O3 O 0.56296(8) -0.1391(2) 0.1289(2) 0.0383(8) Uani 1 1 d . . . . .
O4 O 0.49963(9) -0.0406(3) 0.0972(2) 0.0504(10) Uani 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
C1A C2A 1.372(6) . ?
C1A C5A 1.392(6) . ?
C1A N2A 1.428(5) . ?
C2A C3A 1.385(6) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.397(6) . ?
C3A C9A 1.505(6) . ?
C4A N1A 1.338(6) . ?
C4A C10A 1.456(6) . ?
C5A N1A 1.337(5) . ?
C5A H5A 0.9300 . ?
C6A N3A 1.335(5) . ?
C6A N2A 1.397(5) . ?
C6A S1A 1.597(4) . ?
C7A N3A 1.460(5) . ?
C7A C8A 1.506(5) . ?
C7A C18A 1.545(6) . ?
C7A C17A 1.547(6) . ?
C8A O1A 1.201(5) . ?
C8A N2A 1.387(5) . ?
C9A F1A 1.317(5) . ?
C9A F2A 1.332(5) . ?
C9A F3A 1.346(5) . ?
C10A N4A 1.135(6) . ?
C11A C12A 1.379(5) . ?
C11A C16A 1.389(6) . ?
C11A N3A 1.434(5) . ?
C12A C13A 1.379(5) . ?
C12A H12A 0.9300 . ?
C13A F4A 1.351(4) . ?
C13A C14A 1.384(6) . ?
C14A C15A 1.389(5) . ?
C14A C20A 1.505(5) . ?
C15A C16A 1.388(5) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C17A C19A 1.542(6) . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C18A C19A 1.535(7) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C20A O2A 1.232(4) . ?
C20A N5A 1.318(5) . ?
C21A N5A 1.460(5) . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
N5A H5NA 0.827(19) . ?
C1B C2B 1.359(6) . ?
C1B C5B 1.377(7) . ?
C1B N2B 1.462(6) . ?
C2B C3B 1.400(6) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.411(7) . ?
C3B C9B 1.488(7) . ?
C4B N1B 1.333(6) . ?
C4B C10B 1.431(7) . ?
C5B N1B 1.327(6) . ?
C5B H5B 0.9300 . ?
C6B N3B 1.350(5) . ?
C6B N2B 1.397(5) . ?
C6B S1B 1.584(4) . ?
C7B N3B 1.468(5) . ?
C7B C8B 1.516(6) . ?
C7B C18B 1.543(6) . ?
C7B C17B 1.552(6) . ?
C8B O1B 1.205(5) . ?
C8B N2B 1.384(6) . ?
C9B F2B 1.300(7) . ?
C9B F3B 1.334(6) . ?
C9B F1B 1.359(6) . ?
C10B N4B 1.155(6) . ?
C11B C12B 1.386(5) . ?
C11B C16B 1.393(6) . ?
C11B N3B 1.430(5) . ?
C12B C13B 1.370(6) . ?
C12B H12 0.9300 . ?
C13B F4B 1.367(5) . ?
C13B C14B 1.395(6) . ?
C13B H13D 0.9300 . ?
C14B C15B 1.399(5) . ?
C14B C20B 1.497(5) . ?
C15B F4D 1.362(6) . ?
C15B C16B 1.373(5) . ?
C15B H15B 0.9300 . ?
C16B H16 0.9300 . ?
C17B C19B 1.534(7) . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?
C18B C19B 1.544(6) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C20B O2B 1.239(5) . ?
C20B N5B 1.330(5) . ?
C21B N5B 1.452(5) . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?
N5B H5NB 0.836(19) . ?
C22 O3 1.427(6) . ?
C22 C25 1.483(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 O3 1.438(6) . ?
C23 C24 1.483(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 O4 1.429(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 O4 1.424(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?

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
C2A C1A C5A 120.4(4) . . ?
C2A C1A N2A 120.5(3) . . ?
C5A C1A N2A 119.1(4) . . ?
C1A C2A C3A 118.4(4) . . ?
C1A C2A H2A 120.8 . . ?
C3A C2A H2A 120.8 . . ?
C2A C3A C4A 117.7(4) . . ?
C2A C3A C9A 121.5(4) . . ?
C4A C3A C9A 120.7(4) . . ?
N1A C4A C3A 124.2(4) . . ?
N1A C4A C10A 115.2(4) . . ?
C3A C4A C10A 120.6(4) . . ?
N1A C5A C1A 122.1(4) . . ?
N1A C5A H5A 119.0 . . ?
C1A C5A H5A 119.0 . . ?
N3A C6A N2A 106.8(3) . . ?
N3A C6A S1A 127.8(3) . . ?
N2A C6A S1A 125.2(3) . . ?
N3A C7A C8A 101.4(3) . . ?
N3A C7A C18A 119.4(4) . . ?
C8A C7A C18A 113.9(3) . . ?
N3A C7A C17A 120.9(3) . . ?
C8A C7A C17A 113.6(3) . . ?
C18A C7A C17A 88.3(3) . . ?
O1A C8A N2A 125.1(4) . . ?
O1A C8A C7A 128.3(4) . . ?
N2A C8A C7A 106.5(3) . . ?
F1A C9A F2A 108.7(4) . . ?
F1A C9A F3A 107.4(4) . . ?
F2A C9A F3A 106.1(3) . . ?
F1A C9A C3A 111.8(4) . . ?
F2A C9A C3A 111.2(4) . . ?
F3A C9A C3A 111.3(3) . . ?
N4A C10A C4A 179.4(5) . . ?
C12A C11A C16A 121.3(3) . . ?
C12A C11A N3A 118.7(4) . . ?
C16A C11A N3A 120.0(3) . . ?
C11A C12A C13A 117.9(4) . . ?
C11A C12A H12A 121.0 . . ?
C13A C12A H12A 121.0 . . ?
F4A C13A C12A 118.4(4) . . ?
F4A C13A C14A 118.7(3) . . ?
C12A C13A C14A 122.9(4) . . ?
C13A C14A C15A 117.8(3) . . ?
C13A C14A C20A 119.9(3) . . ?
C15A C14A C20A 122.2(4) . . ?
C16A C15A C14A 120.8(4) . . ?
C16A C15A H15A 119.6 . . ?
C14A C15A H15A 119.6 . . ?
C15A C16A C11A 119.1(4) . . ?
C15A C16A H16A 120.4 . . ?
C11A C16A H16A 120.4 . . ?
C19A C17A C7A 88.5(3) . . ?
C19A C17A H17A 113.9 . . ?
C7A C17A H17A 113.9 . . ?
C19A C17A H17B 113.9 . . ?
C7A C17A H17B 113.9 . . ?
H17A C17A H17B 111.1 . . ?
C19A C18A C7A 88.9(3) . . ?
C19A C18A H18A 113.8 . . ?
C7A C18A H18A 113.8 . . ?
C19A C18A H18B 113.8 . . ?
C7A C18A H18B 113.8 . . ?
H18A C18A H18B 111.1 . . ?
C18A C19A C17A 88.8(3) . . ?
C18A C19A H19A 113.9 . . ?
C17A C19A H19A 113.9 . . ?
C18A C19A H19B 113.8 . . ?
C17A C19A H19B 113.9 . . ?
H19A C19A H19B 111.1 . . ?
O2A C20A N5A 124.3(3) . . ?
O2A C20A C14A 120.1(3) . . ?
N5A C20A C14A 115.6(3) . . ?
N5A C21A H21A 109.5 . . ?
N5A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
N5A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C5A N1A C4A 117.2(4) . . ?
C8A N2A C6A 111.7(3) . . ?
C8A N2A C1A 123.2(3) . . ?
C6A N2A C1A 124.1(3) . . ?
C6A N3A C11A 122.5(3) . . ?
C6A N3A C7A 113.3(3) . . ?
C11A N3A C7A 123.6(3) . . ?
C20A N5A C21A 122.3(3) . . ?
C20A N5A H5NA 120(3) . . ?
C21A N5A H5NA 117(3) . . ?
C2B C1B C5B 120.4(4) . . ?
C2B C1B N2B 120.2(4) . . ?
C5B C1B N2B 119.4(4) . . ?
C1B C2B C3B 117.7(5) . . ?
C1B C2B H2B 121.1 . . ?
C3B C2B H2B 121.1 . . ?
C2B C3B C4B 117.6(4) . . ?
C2B C3B C9B 123.5(5) . . ?
C4B C3B C9B 118.9(4) . . ?
N1B C4B C3B 124.1(4) . . ?
N1B C4B C10B 112.9(5) . . ?
C3B C4B C10B 122.9(4) . . ?
N1B C5B C1B 124.0(5) . . ?
N1B C5B H5B 118.0 . . ?
C1B C5B H5B 118.0 . . ?
N3B C6B N2B 107.0(3) . . ?
N3B C6B S1B 128.5(3) . . ?
N2B C6B S1B 124.4(3) . . ?
N3B C7B C8B 101.1(3) . . ?
N3B C7B C18B 120.0(3) . . ?
C8B C7B C18B 115.0(4) . . ?
N3B C7B C17B 120.0(4) . . ?
C8B C7B C17B 113.0(3) . . ?
C18B C7B C17B 88.4(3) . . ?
O1B C8B N2B 125.1(4) . . ?
O1B C8B C7B 127.7(4) . . ?
N2B C8B C7B 107.1(3) . . ?
F2B C9B F3B 106.7(5) . . ?
F2B C9B F1B 107.6(4) . . ?
F3B C9B F1B 106.7(5) . . ?
F2B C9B C3B 114.5(5) . . ?
F3B C9B C3B 111.3(4) . . ?
F1B C9B C3B 109.6(5) . . ?
N4B C10B C4B 176.8(6) . . ?
C12B C11B C16B 120.2(4) . . ?
C12B C11B N3B 120.3(4) . . ?
C16B C11B N3B 119.5(3) . . ?
C13B C12B C11B 119.3(4) . . ?
C13B C12B H12 120.4 . . ?
C11B C12B H12 120.4 . . ?
F4B C13B C12B 117.1(4) . . ?
F4B C13B C14B 120.0(4) . . ?
C12B C13B C14B 122.5(4) . . ?
C12B C13B H13D 118.7 . . ?
C14B C13B H13D 118.7 . . ?
C13B C14B C15B 116.6(4) . . ?
C13B C14B C20B 120.7(3) . . ?
C15B C14B C20B 122.7(4) . . ?
F4D C15B C16B 116.5(4) . . ?
F4D C15B C14B 120.3(4) . . ?
C16B C15B C14B 122.3(4) . . ?
C16B C15B H15B 118.9 . . ?
C14B C15B H15B 118.9 . . ?
C15B C16B C11B 119.1(3) . . ?
C15B C16B H16 120.4 . . ?
C11B C16B H16 120.4 . . ?
C19B C17B C7B 88.4(3) . . ?
C19B C17B H17C 113.9 . . ?
C7B C17B H17C 113.9 . . ?
C19B C17B H17D 113.9 . . ?
C7B C17B H17D 113.9 . . ?
H17C C17B H17D 111.1 . . ?
C7B C18B C19B 88.4(3) . . ?
C7B C18B H18C 113.9 . . ?
C19B C18B H18C 113.9 . . ?
C7B C18B H18D 113.9 . . ?
C19B C18B H18D 113.9 . . ?
H18C C18B H18D 111.1 . . ?
C17B C19B C18B 89.1(3) . . ?
C17B C19B H19C 113.8 . . ?
C18B C19B H19C 113.8 . . ?
C17B C19B H19D 113.8 . . ?
C18B C19B H19D 113.8 . . ?
H19C C19B H19D 111.0 . . ?
O2B C20B N5B 123.3(4) . . ?
O2B C20B C14B 120.8(4) . . ?
N5B C20B C14B 115.9(3) . . ?
N5B C21B H21D 109.5 . . ?
N5B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
N5B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C5B N1B C4B 116.2(5) . . ?
C8B N2B C6B 111.7(3) . . ?
C8B N2B C1B 125.6(3) . . ?
C6B N2B C1B 121.6(3) . . ?
C6B N3B C11B 121.0(3) . . ?
C6B N3B C7B 113.1(3) . . ?
C11B N3B C7B 125.9(3) . . ?
C20B N5B C21B 121.6(3) . . ?
C20B N5B H5NB 122(4) . . ?
C21B N5B H5NB 116(4) . . ?
O3 C22 C25 111.5(4) . . ?
O3 C22 H22A 109.3 . . ?
C25 C22 H22A 109.3 . . ?
O3 C22 H22B 109.3 . . ?
C25 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
O3 C23 C24 111.9(4) . . ?
O3 C23 H23A 109.2 . . ?
C24 C23 H23A 109.2 . . ?
O3 C23 H23B 109.2 . . ?
C24 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
O4 C24 C23 111.3(4) . . ?
O4 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 . . ?
O4 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
O4 C25 C22 111.1(4) . . ?
O4 C25 H25A 109.4 . . ?
C22 C25 H25A 109.4 . . ?
O4 C25 H25B 109.4 . . ?
C22 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
C22 O3 C23 108.8(4) . . ?
C25 O4 C24 109.0(4) . . ?

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
C5A C1A C2A C3A 0.1(6) . . . . ?
N2A C1A C2A C3A 177.8(3) . . . . ?
C1A C2A C3A C4A 0.5(5) . . . . ?
C1A C2A C3A C9A -179.4(4) . . . . ?
C2A C3A C4A N1A -1.3(6) . . . . ?
C9A C3A C4A N1A 178.6(4) . . . . ?
C2A C3A C4A C10A 178.8(4) . . . . ?
C9A C3A C4A C10A -1.3(6) . . . . ?
C2A C1A C5A N1A 0.0(6) . . . . ?
N2A C1A C5A N1A -177.7(4) . . . . ?
N3A C7A C8A O1A 177.9(5) . . . . ?
C18A C7A C8A O1A -52.5(7) . . . . ?
C17A C7A C8A O1A 46.6(7) . . . . ?
N3A C7A C8A N2A -2.8(4) . . . . ?
C18A C7A C8A N2A 126.8(4) . . . . ?
C17A C7A C8A N2A -134.1(4) . . . . ?
C2A C3A C9A F1A 6.6(5) . . . . ?
C4A C3A C9A F1A -173.3(4) . . . . ?
C2A C3A C9A F2A -115.1(4) . . . . ?
C4A C3A C9A F2A 65.0(5) . . . . ?
C2A C3A C9A F3A 126.8(4) . . . . ?
C4A C3A C9A F3A -53.1(5) . . . . ?
C16A C11A C12A C13A -1.6(6) . . . . ?
N3A C11A C12A C13A -179.8(3) . . . . ?
C11A C12A C13A F4A 178.2(3) . . . . ?
C11A C12A C13A C14A -0.5(6) . . . . ?
F4A C13A C14A C15A -177.2(3) . . . . ?
C12A C13A C14A C15A 1.5(6) . . . . ?
F4A C13A C14A C20A 4.6(5) . . . . ?
C12A C13A C14A C20A -176.7(4) . . . . ?
C13A C14A C15A C16A -0.4(6) . . . . ?
C20A C14A C15A C16A 177.7(4) . . . . ?
C14A C15A C16A C11A -1.6(6) . . . . ?
C12A C11A C16A C15A 2.7(6) . . . . ?
N3A C11A C16A C15A -179.2(4) . . . . ?
N3A C7A C17A C19A 141.2(4) . . . . ?
C8A C7A C17A C19A -97.9(4) . . . . ?
C18A C7A C17A C19A 17.6(3) . . . . ?
N3A C7A C18A C19A -142.6(4) . . . . ?
C8A C7A C18A C19A 97.5(4) . . . . ?
C17A C7A C18A C19A -17.6(3) . . . . ?
C7A C18A C19A C17A 17.7(3) . . . . ?
C7A C17A C19A C18A -17.7(3) . . . . ?
C13A C14A C20A O2A 70.5(5) . . . . ?
C15A C14A C20A O2A -107.5(5) . . . . ?
C13A C14A C20A N5A -108.2(4) . . . . ?
C15A C14A C20A N5A 73.8(5) . . . . ?
C1A C5A N1A C4A -0.6(6) . . . . ?
C3A C4A N1A C5A 1.3(6) . . . . ?
C10A C4A N1A C5A -178.8(4) . . . . ?
O1A C8A N2A C6A 179.9(5) . . . . ?
C7A C8A N2A C6A 0.5(5) . . . . ?
O1A C8A N2A C1A -10.6(7) . . . . ?
C7A C8A N2A C1A 170.0(3) . . . . ?
N3A C6A N2A C8A 2.3(5) . . . . ?
S1A C6A N2A C8A -172.5(3) . . . . ?
N3A C6A N2A C1A -167.1(4) . . . . ?
S1A C6A N2A C1A 18.1(6) . . . . ?
C2A C1A N2A C8A -98.9(5) . . . . ?
C5A C1A N2A C8A 78.8(5) . . . . ?
C2A C1A N2A C6A 69.4(5) . . . . ?
C5A C1A N2A C6A -112.9(4) . . . . ?
N2A C6A N3A C11A -176.3(3) . . . . ?
S1A C6A N3A C11A -1.7(6) . . . . ?
N2A C6A N3A C7A -4.3(5) . . . . ?
S1A C6A N3A C7A 170.3(3) . . . . ?
C12A C11A N3A C6A -106.1(5) . . . . ?
C16A C11A N3A C6A 75.8(5) . . . . ?
C12A C11A N3A C7A 82.8(5) . . . . ?
C16A C11A N3A C7A -95.4(5) . . . . ?
C8A C7A N3A C6A 4.4(4) . . . . ?
C18A C7A N3A C6A -121.6(4) . . . . ?
C17A C7A N3A C6A 131.1(4) . . . . ?
C8A C7A N3A C11A 176.3(4) . . . . ?
C18A C7A N3A C11A 50.3(5) . . . . ?
C17A C7A N3A C11A -57.1(5) . . . . ?
O2A C20A N5A C21A 2.7(6) . . . . ?
C14A C20A N5A C21A -178.7(4) . . . . ?
C5B C1B C2B C3B 1.2(6) . . . . ?
N2B C1B C2B C3B -179.0(4) . . . . ?
C1B C2B C3B C4B -1.8(6) . . . . ?
C1B C2B C3B C9B 179.9(4) . . . . ?
C2B C3B C4B N1B 0.9(7) . . . . ?
C9B C3B C4B N1B 179.3(5) . . . . ?
C2B C3B C4B C10B -176.9(4) . . . . ?
C9B C3B C4B C10B 1.5(7) . . . . ?
C2B C1B C5B N1B 0.4(8) . . . . ?
N2B C1B C5B N1B -179.3(5) . . . . ?
N3B C7B C8B O1B -176.9(5) . . . . ?
C18B C7B C8B O1B 52.2(7) . . . . ?
C17B C7B C8B O1B -47.3(7) . . . . ?
N3B C7B C8B N2B -0.1(4) . . . . ?
C18B C7B C8B N2B -130.9(4) . . . . ?
C17B C7B C8B N2B 129.6(4) . . . . ?
C2B C3B C9B F2B -127.8(5) . . . . ?
C4B C3B C9B F2B 53.9(6) . . . . ?
C2B C3B C9B F3B 111.1(5) . . . . ?
C4B C3B C9B F3B -67.2(6) . . . . ?
C2B C3B C9B F1B -6.7(6) . . . . ?
C4B C3B C9B F1B 175.0(4) . . . . ?
C16B C11B C12B C13B 0.3(6) . . . . ?
N3B C11B C12B C13B 178.0(4) . . . . ?
C11B C12B C13B F4B -172.7(4) . . . . ?
C11B C12B C13B C14B -0.3(6) . . . . ?
F4B C13B C14B C15B 172.0(4) . . . . ?
C12B C13B C14B C15B -0.1(6) . . . . ?
F4B C13B C14B C20B -6.0(6) . . . . ?
C12B C13B C14B C20B -178.2(4) . . . . ?
C13B C14B C15B F4D -168.3(4) . . . . ?
C20B C14B C15B F4D 9.7(6) . . . . ?
C13B C14B C15B C16B 0.6(6) . . . . ?
C20B C14B C15B C16B 178.6(4) . . . . ?
F4D C15B C16B C11B 168.7(4) . . . . ?
C14B C15B C16B C11B -0.6(6) . . . . ?
C12B C11B C16B C15B 0.1(6) . . . . ?
N3B C11B C16B C15B -177.6(3) . . . . ?
N3B C7B C17B C19B -142.2(4) . . . . ?
C8B C7B C17B C19B 98.6(4) . . . . ?
C18B C7B C17B C19B -18.0(3) . . . . ?
N3B C7B C18B C19B 142.1(4) . . . . ?
C8B C7B C18B C19B -96.9(4) . . . . ?
C17B C7B C18B C19B 17.9(4) . . . . ?
C7B C17B C19B C18B 18.0(4) . . . . ?
C7B C18B C19B C17B -18.1(4) . . . . ?
C13B C14B C20B O2B 43.7(5) . . . . ?
C15B C14B C20B O2B -134.2(4) . . . . ?
C13B C14B C20B N5B -136.2(4) . . . . ?
C15B C14B C20B N5B 45.9(5) . . . . ?
C1B C5B N1B C4B -1.4(8) . . . . ?
C3B C4B N1B C5B 0.7(7) . . . . ?
C10B C4B N1B C5B 178.6(5) . . . . ?
O1B C8B N2B C6B 176.2(5) . . . . ?
C7B C8B N2B C6B -0.7(5) . . . . ?
O1B C8B N2B C1B 8.3(7) . . . . ?
C7B C8B N2B C1B -168.7(4) . . . . ?
N3B C6B N2B C8B 1.3(5) . . . . ?
S1B C6B N2B C8B -179.1(3) . . . . ?
N3B C6B N2B C1B 169.8(3) . . . . ?
S1B C6B N2B C1B -10.6(6) . . . . ?
C2B C1B N2B C8B -66.7(6) . . . . ?
C5B C1B N2B C8B 113.1(5) . . . . ?
C2B C1B N2B C6B 126.5(4) . . . . ?
C5B C1B N2B C6B -53.7(6) . . . . ?
N2B C6B N3B C11B -178.8(3) . . . . ?
S1B C6B N3B C11B 1.6(6) . . . . ?
N2B C6B N3B C7B -1.3(4) . . . . ?
S1B C6B N3B C7B 179.1(3) . . . . ?
C12B C11B N3B C6B -98.1(5) . . . . ?
C16B C11B N3B C6B 79.7(5) . . . . ?
C12B C11B N3B C7B 84.8(5) . . . . ?
C16B C11B N3B C7B -97.5(5) . . . . ?
C8B C7B N3B C6B 0.9(4) . . . . ?
C18B C7B N3B C6B 128.5(4) . . . . ?
C17B C7B N3B C6B -124.2(4) . . . . ?
C8B C7B N3B C11B 178.2(4) . . . . ?
C18B C7B N3B C11B -54.1(6) . . . . ?
C17B C7B N3B C11B 53.2(5) . . . . ?
O2B C20B N5B C21B 1.3(6) . . . . ?
C14B C20B N5B C21B -178.8(4) . . . . ?
O3 C23 C24 O4 56.9(6) . . . . ?
O3 C22 C25 O4 -59.2(6) . . . . ?
C25 C22 O3 C23 56.4(5) . . . . ?
C24 C23 O3 C22 -55.4(5) . . . . ?
C22 C25 O4 C24 57.8(6) . . . . ?
C23 C24 O4 C25 -56.8(6) . . . . ?

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
_geom_hbond_publ_flag
N5A H5NA O2B 0.827(19) 2.08(2) 2.904(4) 173(4) 6_575 yes
N5B H5NB O2A 0.836(19) 2.02(2) 2.849(4) 173(5) . yes
C2A H2A O3 0.93 2.47 3.179(5) 133 1_565 yes
C5A H5A S1B 0.93 2.82 3.681(4) 155 6_565 yes
C15A H15A S1B 0.93 2.79 3.611(4) 148 7_666 yes
C5B H5B S1A 0.93 2.67 3.412(5) 138 . yes
C22 H22A N4B 0.97 2.61 3.305(7) 129 . yes

_refine_diff_density_max         0.831
_refine_diff_density_min         -0.882
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_KB06_0m_APA-BUT
_database_code_depnum_ccdc_archive 'CCDC 2152155'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-02-15 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            Apalutamide-2-butanol-1:0.5
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C21 H15 F4 N5 O2 S), C4 H10 O'
_chemical_formula_sum            'C46 H40 F8 N10 O5 S2'
_chemical_formula_weight         1029.00

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'
F F 0.0171 0.0103 '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                   19.3859(8)
_cell_length_b                   16.1915(3)
_cell_length_c                   7.38330(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.171(5)
_cell_angle_gamma                90
_cell_volume                     2317.51(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9867
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      30.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             1060
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.206
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5562
_exptl_absorpt_correction_T_max  0.7215
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40466
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.449
_diffrn_reflns_theta_max         30.522
_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             7083
_reflns_number_gt                6096
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+2.7100P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7083
_refine_ls_number_parameters     411
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1357
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_restrained_S_all      1.164
_refine_ls_shift/su_max          0.002
_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
C1 C -0.47670(9) 1.13429(10) 0.7931(2) 0.0169(3) Uani 1 1 d . . . . .
C2 C -0.50635(9) 1.11169(11) 0.6297(3) 0.0193(3) Uani 1 1 d . . . . .
H2 H -0.479827 1.085467 0.538283 0.023 Uiso 1 1 calc R U . . .
C3 C -0.57587(9) 1.12834(11) 0.6031(3) 0.0211(4) Uani 1 1 d . . . . .
C4 C -0.61221(9) 1.16707(12) 0.7421(3) 0.0233(4) Uani 1 1 d . . . . .
C5 C -0.51708(9) 1.17131(11) 0.9256(3) 0.0210(3) Uani 1 1 d . . . . .
H5 H -0.496246 1.185314 1.038100 0.025 Uiso 1 1 calc R U . . .
C6 C -0.35166(8) 1.14403(10) 0.7163(2) 0.0143(3) Uani 1 1 d . . . . .
C7 C -0.30492(9) 1.06814(10) 0.9581(2) 0.0164(3) Uani 1 1 d . . . . .
C8 C -0.38206(9) 1.07461(11) 0.9791(2) 0.0179(3) Uani 1 1 d . . . . .
C9 C -0.60890(10) 1.09911(12) 0.4302(3) 0.0258(4) Uani 1 1 d . . . . .
C10 C -0.68475(11) 1.18862(14) 0.7265(4) 0.0343(5) Uani 1 1 d . . . . .
C11 C -0.22625(9) 1.13061(11) 0.7207(2) 0.0169(3) Uani 1 1 d . . . . .
C12 C -0.19667(9) 1.20685(11) 0.7559(2) 0.0179(3) Uani 1 1 d . . . . .
H12 H -0.221065 1.247698 0.822270 0.022 Uiso 1 1 calc R U . . .
C13 C -0.12428(11) 1.08735(14) 0.5694(4) 0.0351(5) Uani 1 1 d . . . . .
H13D H -0.099325 1.045947 0.506238 0.042 Uiso 0.455(4) 1 calc R U P A 2
C14 C -0.09276(10) 1.16254(13) 0.6023(3) 0.0266(4) Uani 1 1 d . . . . .
C15 C -0.13090(9) 1.22221(12) 0.6924(3) 0.0206(3) Uani 1 1 d . . . . .
H15 H -0.111199 1.275274 0.710985 0.025 Uiso 0.545(4) 1 calc R U P A 1
C16 C -0.19062(10) 1.07033(13) 0.6250(3) 0.0270(4) Uani 1 1 d . . . . .
H16 H -0.211483 1.018611 0.598534 0.032 Uiso 1 1 calc R U . . .
C17 C -0.26359(10) 1.09356(11) 1.1293(2) 0.0197(3) Uani 1 1 d . . . . .
H17A H -0.218646 1.119854 1.102686 0.024 Uiso 1 1 calc R U . . .
H17B H -0.290430 1.126828 1.216809 0.024 Uiso 1 1 calc R U . . .
C18 C -0.27795(11) 0.97843(12) 0.9824(3) 0.0250(4) Uani 1 1 d . . . . .
H18A H -0.314300 0.935683 0.973018 0.030 Uiso 1 1 calc R U . . .
H18B H -0.237998 0.964732 0.904724 0.030 Uiso 1 1 calc R U . . .
C19 C -0.25820(13) 1.00128(13) 1.1796(3) 0.0316(5) Uani 1 1 d . . . . .
H19A H -0.292489 0.983301 1.270554 0.038 Uiso 1 1 calc R U . . .
H19B H -0.211111 0.983724 1.214754 0.038 Uiso 1 1 calc R U . . .
S1 S -0.35980(2) 1.20150(3) 0.53292(6) 0.01747(10) Uani 1 1 d . . . . .
F1 F -0.63166(10) 1.02281(9) 0.4459(2) 0.0490(4) Uani 1 1 d . . . . .
F2 F -0.6523(3) 1.1483(4) 0.3520(8) 0.0503(15) Uani 0.545(4) 1 d . . P A 3
F3 F -0.5604(2) 1.0796(3) 0.2931(6) 0.0388(9) Uani 0.545(4) 1 d . . P A 3
F4 F -0.08580(13) 1.02542(16) 0.5048(4) 0.0384(7) Uani 0.545(4) 1 d . . P A 3
F2D F -0.6722(3) 1.1351(5) 0.4081(9) 0.0400(14) Uani 0.455(4) 1 d . . P A 4
F3D F -0.5715(3) 1.1180(3) 0.2989(7) 0.0416(12) Uani 0.455(4) 1 d . . P A 4
F4D F -0.10348(12) 1.29910(15) 0.7038(4) 0.0234(7) Uani 0.455(4) 1 d . . P A 4
O1 O -0.41764(7) 1.04681(9) 1.0978(2) 0.0276(3) Uani 1 1 d . . . . .
N1 N -0.58376(8) 1.18795(11) 0.9013(2) 0.0249(3) Uani 1 1 d . . . . .
N2 N -0.40602(7) 1.11868(9) 0.8279(2) 0.0153(3) Uani 1 1 d . . . . .
N3 N -0.29363(7) 1.11272(9) 0.78855(19) 0.0160(3) Uani 1 1 d . . . . .
N4 N -0.74167(11) 1.20583(16) 0.7190(4) 0.0547(7) Uani 1 1 d . . . . .
C20 C -0.0220(5) 1.1747(6) 0.5128(9) 0.0198(13) Uani 0.5 1 d D . P B 5
N5 N 0.02373(17) 1.2087(3) 0.6220(5) 0.0308(8) Uani 0.5 1 d D . P B 5
H5N H 0.010615 1.226649 0.729012 0.037 Uiso 0.5 1 calc DR U P B 5
O2 O -0.00763(16) 1.1504(2) 0.3582(4) 0.0315(7) Uani 0.5 1 d . . P B 5
C21 C 0.0959(2) 1.2170(4) 0.5683(8) 0.0428(13) Uani 0.5 1 d D . P B 5
H21A H 0.123455 1.234803 0.672741 0.064 Uiso 0.5 1 calc R U P B 5
H21B H 0.099638 1.258076 0.471394 0.064 Uiso 0.5 1 calc R U P B 5
H21C H 0.113035 1.163624 0.524785 0.064 Uiso 0.5 1 calc R U P B 5
C20D C -0.0188(6) 1.1852(7) 0.5647(10) 0.0259(16) Uani 0.5 1 d . . P B 6
N5D N 0.03092(17) 1.1339(3) 0.6186(5) 0.0305(8) Uani 0.5 1 d . . P B 6
H5ND H 0.020289 1.088310 0.677175 0.037 Uiso 0.5 1 calc R U P B 6
O2D O -0.00987(15) 1.2489(2) 0.4782(4) 0.0324(7) Uani 0.5 1 d . . P B 6
C21D C 0.1031(2) 1.1532(4) 0.5806(8) 0.0407(12) Uani 0.5 1 d . . P B 6
H21D H 0.132961 1.118706 0.656585 0.061 Uiso 0.5 1 calc R U P B 6
H21E H 0.111810 1.211557 0.607077 0.061 Uiso 0.5 1 calc R U P B 6
H21F H 0.112774 1.142205 0.452672 0.061 Uiso 0.5 1 calc R U P B 6
C22 C 0.0719(3) 1.0289(4) -0.0536(9) 0.0519(14) Uani 0.5 1 d . . P C -7
H22A H 0.113437 0.996091 -0.029543 0.078 Uiso 0.5 1 calc R U P C -7
H22B H 0.075963 1.082533 0.007103 0.078 Uiso 0.5 1 calc R U P C -7
H22C H 0.066986 1.037460 -0.184423 0.078 Uiso 0.5 1 calc R U P C -7
C23 C 0.0045(3) 0.9802(3) 0.0228(7) 0.0386(11) Uani 0.5 1 d . . P C -7
H23 H 0.027200 0.929311 0.071462 0.046 Uiso 0.5 1 calc R U P C -7
C24 C -0.0349(4) 0.9452(4) -0.1189(8) 0.0620(18) Uani 0.5 1 d . . P C -7
H24A H -0.007542 0.901707 -0.179686 0.074 Uiso 0.5 1 calc R U P C -7
H24B H -0.045768 0.988339 -0.209608 0.074 Uiso 0.5 1 calc R U P C -7
C25 C -0.1021(3) 0.9077(5) -0.0487(11) 0.075(2) Uani 0.5 1 d . . P C -7
H25A H -0.141146 0.930244 -0.117407 0.112 Uiso 0.5 1 calc R U P C -7
H25B H -0.107551 0.921271 0.079865 0.112 Uiso 0.5 1 calc R U P C -7
H25C H -0.100785 0.847572 -0.063413 0.112 Uiso 0.5 1 calc R U P C -7
O3 O -0.0205(2) 1.0091(2) 0.1671(5) 0.0481(9) Uani 0.5 1 d . . P C -7
H3O H 0.008738 1.039617 0.217824 0.072 Uiso 0.5 1 calc R U P C -7


_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
C1 C2 1.384(3) . ?
C1 C5 1.391(3) . ?
C1 N2 1.416(2) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(3) . ?
C3 C9 1.503(3) . ?
C4 N1 1.340(3) . ?
C4 C10 1.453(3) . ?
C5 N1 1.332(2) . ?
C5 H5 0.9500 . ?
C6 N3 1.343(2) . ?
C6 N2 1.401(2) . ?
C6 S1 1.6499(17) . ?
C7 N3 1.462(2) . ?
C7 C8 1.507(2) . ?
C7 C17 1.550(2) . ?
C7 C18 1.554(2) . ?
C8 O1 1.204(2) . ?
C8 N2 1.403(2) . ?
C9 F3D 1.250(6) . ?
C9 F2 1.294(6) . ?
C9 F1 1.317(2) . ?
C9 F2D 1.368(7) . ?
C9 F3 1.420(5) . ?
C10 N4 1.139(3) . ?
C11 C12 1.385(2) . ?
C11 C16 1.390(3) . ?
C11 N3 1.430(2) . ?
C12 C15 1.382(2) . ?
C12 H12 0.9500 . ?
C13 F4 1.339(3) . ?
C13 C16 1.379(3) . ?
C13 C14 1.383(3) . ?
C13 H13D 0.9500 . ?
C14 C15 1.388(3) . ?
C14 C20D 1.506(11) . ?
C14 C20 1.538(10) . ?
C15 F4D 1.356(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C19 1.543(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.550(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O2 1.239(7) . ?
C20 N5 1.317(8) . ?
N5 C21 1.462(5) . ?
N5 H5N 0.8800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C20D O2D 1.226(12) . ?
C20D N5D 1.333(12) . ?
N5D C21D 1.461(5) . ?
N5D H5ND 0.8800 . ?
C21D H21D 0.9800 . ?
C21D H21E 0.9800 . ?
C21D H21F 0.9800 . ?
C22 C23 1.629(9) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 O3 1.262(6) . ?
C23 C24 1.413(9) . ?
C23 H23 1.0000 . ?
C24 C25 1.529(11) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
O3 H3O 0.8400 . ?

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
C2 C1 C5 119.60(17) . . ?
C2 C1 N2 120.68(16) . . ?
C5 C1 N2 119.71(16) . . ?
C1 C2 C3 118.22(18) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 118.38(17) . . ?
C2 C3 C9 118.06(18) . . ?
C4 C3 C9 123.46(17) . . ?
N1 C4 C3 123.44(17) . . ?
N1 C4 C10 113.85(19) . . ?
C3 C4 C10 122.71(19) . . ?
N1 C5 C1 122.72(18) . . ?
N1 C5 H5 118.6 . . ?
C1 C5 H5 118.6 . . ?
N3 C6 N2 106.64(14) . . ?
N3 C6 S1 128.08(13) . . ?
N2 C6 S1 125.29(13) . . ?
N3 C7 C8 101.82(14) . . ?
N3 C7 C17 119.26(14) . . ?
C8 C7 C17 114.08(14) . . ?
N3 C7 C18 120.60(15) . . ?
C8 C7 C18 112.75(15) . . ?
C17 C7 C18 88.92(13) . . ?
O1 C8 N2 125.47(17) . . ?
O1 C8 C7 128.27(17) . . ?
N2 C8 C7 106.25(14) . . ?
F3D C9 F1 119.5(3) . . ?
F2 C9 F1 113.5(3) . . ?
F3D C9 F2D 109.0(4) . . ?
F1 C9 F2D 96.3(3) . . ?
F2 C9 F3 104.5(3) . . ?
F1 C9 F3 94.4(2) . . ?
F3D C9 C3 109.6(3) . . ?
F2 C9 C3 117.4(3) . . ?
F1 C9 C3 111.28(17) . . ?
F2D C9 C3 110.3(3) . . ?
F3 C9 C3 113.2(2) . . ?
N4 C10 C4 178.2(3) . . ?
C12 C11 C16 121.00(16) . . ?
C12 C11 N3 119.53(15) . . ?
C16 C11 N3 119.45(16) . . ?
C15 C12 C11 118.58(16) . . ?
C15 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
F4 C13 C16 118.5(2) . . ?
F4 C13 C14 118.4(2) . . ?
C16 C13 C14 122.38(19) . . ?
C16 C13 H13D 118.8 . . ?
C14 C13 H13D 118.8 . . ?
C13 C14 C15 117.47(18) . . ?
C13 C14 C20D 127.0(4) . . ?
C15 C14 C20D 115.3(4) . . ?
C13 C14 C20 115.6(4) . . ?
C15 C14 C20 126.5(4) . . ?
F4D C15 C12 120.38(19) . . ?
F4D C15 C14 117.38(19) . . ?
C12 C15 C14 122.04(17) . . ?
C12 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C13 C16 C11 118.44(18) . . ?
C13 C16 H16 120.8 . . ?
C11 C16 H16 120.8 . . ?
C19 C17 C7 88.49(14) . . ?
C19 C17 H17A 113.9 . . ?
C7 C17 H17A 113.9 . . ?
C19 C17 H17B 113.9 . . ?
C7 C17 H17B 113.9 . . ?
H17A C17 H17B 111.1 . . ?
C19 C18 C7 88.13(14) . . ?
C19 C18 H18A 114.0 . . ?
C7 C18 H18A 114.0 . . ?
C19 C18 H18B 114.0 . . ?
C7 C18 H18B 114.0 . . ?
H18A C18 H18B 111.2 . . ?
C17 C19 C18 89.35(14) . . ?
C17 C19 H19A 113.8 . . ?
C18 C19 H19A 113.8 . . ?
C17 C19 H19B 113.8 . . ?
C18 C19 H19B 113.8 . . ?
H19A C19 H19B 111.0 . . ?
C5 N1 C4 117.62(17) . . ?
C6 N2 C8 111.67(14) . . ?
C6 N2 C1 124.73(14) . . ?
C8 N2 C1 123.60(14) . . ?
C6 N3 C11 123.33(14) . . ?
C6 N3 C7 113.52(14) . . ?
C11 N3 C7 122.62(14) . . ?
O2 C20 N5 123.0(8) . . ?
O2 C20 C14 123.9(7) . . ?
N5 C20 C14 112.9(5) . . ?
C20 N5 C21 121.0(5) . . ?
C20 N5 H5N 119.5 . . ?
C21 N5 H5N 119.5 . . ?
N5 C21 H21A 109.5 . . ?
N5 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N5 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2D C20D N5D 125.2(9) . . ?
O2D C20D C14 115.9(8) . . ?
N5D C20D C14 118.7(8) . . ?
C20D N5D C21D 120.1(6) . . ?
C20D N5D H5ND 120.0 . . ?
C21D N5D H5ND 120.0 . . ?
N5D C21D H21D 109.5 . . ?
N5D C21D H21E 109.5 . . ?
H21D C21D H21E 109.5 . . ?
N5D C21D H21F 109.5 . . ?
H21D C21D H21F 109.5 . . ?
H21E C21D H21F 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 C24 124.4(6) . . ?
O3 C23 C22 115.1(5) . . ?
C24 C23 C22 111.8(5) . . ?
O3 C23 H23 99.9 . . ?
C24 C23 H23 99.9 . . ?
C22 C23 H23 99.9 . . ?
C23 C24 C25 111.6(5) . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24B 109.3 . . ?
C25 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 O3 H3O 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
C5 C1 C2 C3 1.1(3) . . . . ?
N2 C1 C2 C3 179.87(15) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C1 C2 C3 C9 -176.35(16) . . . . ?
C2 C3 C4 N1 -1.0(3) . . . . ?
C9 C3 C4 N1 175.18(18) . . . . ?
C2 C3 C4 C10 178.80(18) . . . . ?
C9 C3 C4 C10 -5.0(3) . . . . ?
C2 C1 C5 N1 -1.4(3) . . . . ?
N2 C1 C5 N1 179.76(16) . . . . ?
N3 C7 C8 O1 179.21(19) . . . . ?
C17 C7 C8 O1 -51.0(3) . . . . ?
C18 C7 C8 O1 48.5(3) . . . . ?
N3 C7 C8 N2 0.63(17) . . . . ?
C17 C7 C8 N2 130.46(15) . . . . ?
C18 C7 C8 N2 -130.04(15) . . . . ?
C2 C3 C9 F3D -47.2(4) . . . . ?
C4 C3 C9 F3D 136.6(3) . . . . ?
C2 C3 C9 F2 -139.7(3) . . . . ?
C4 C3 C9 F2 44.1(4) . . . . ?
C2 C3 C9 F1 87.2(2) . . . . ?
C4 C3 C9 F1 -89.0(2) . . . . ?
C2 C3 C9 F2D -167.2(3) . . . . ?
C4 C3 C9 F2D 16.6(4) . . . . ?
C2 C3 C9 F3 -17.7(3) . . . . ?
C4 C3 C9 F3 166.1(3) . . . . ?
C16 C11 C12 C15 0.5(3) . . . . ?
N3 C11 C12 C15 178.64(16) . . . . ?
F4 C13 C14 C15 -171.2(2) . . . . ?
C16 C13 C14 C15 -1.0(4) . . . . ?
C16 C13 C14 C20D 173.6(5) . . . . ?
C16 C13 C14 C20 -173.4(4) . . . . ?
C11 C12 C15 F4D 171.7(2) . . . . ?
C11 C12 C15 C14 -3.0(3) . . . . ?
C13 C14 C15 F4D -171.6(2) . . . . ?
C13 C14 C15 C12 3.2(3) . . . . ?
C20D C14 C15 C12 -172.0(4) . . . . ?
C20 C14 C15 C12 174.7(4) . . . . ?
F4 C13 C16 C11 168.9(2) . . . . ?
C14 C13 C16 C11 -1.3(4) . . . . ?
C12 C11 C16 C13 1.6(3) . . . . ?
N3 C11 C16 C13 -176.5(2) . . . . ?
N3 C7 C17 C19 -141.96(17) . . . . ?
C8 C7 C17 C19 97.54(17) . . . . ?
C18 C7 C17 C19 -16.99(15) . . . . ?
N3 C7 C18 C19 140.76(17) . . . . ?
C8 C7 C18 C19 -98.84(17) . . . . ?
C17 C7 C18 C19 16.92(16) . . . . ?
C7 C17 C19 C18 17.04(15) . . . . ?
C7 C18 C19 C17 -17.00(15) . . . . ?
C1 C5 N1 C4 0.5(3) . . . . ?
C3 C4 N1 C5 0.7(3) . . . . ?
C10 C4 N1 C5 -179.11(18) . . . . ?
N3 C6 N2 C8 3.44(18) . . . . ?
S1 C6 N2 C8 -176.41(13) . . . . ?
N3 C6 N2 C1 -175.85(15) . . . . ?
S1 C6 N2 C1 4.3(2) . . . . ?
O1 C8 N2 C6 178.88(18) . . . . ?
C7 C8 N2 C6 -2.49(18) . . . . ?
O1 C8 N2 C1 -1.8(3) . . . . ?
C7 C8 N2 C1 176.80(15) . . . . ?
C2 C1 N2 C6 54.1(2) . . . . ?
C5 C1 N2 C6 -127.16(18) . . . . ?
C2 C1 N2 C8 -125.14(18) . . . . ?
C5 C1 N2 C8 53.6(2) . . . . ?
N2 C6 N3 C11 -174.88(15) . . . . ?
S1 C6 N3 C11 5.0(2) . . . . ?
N2 C6 N3 C7 -3.03(19) . . . . ?
S1 C6 N3 C7 176.81(13) . . . . ?
C12 C11 N3 C6 75.1(2) . . . . ?
C16 C11 N3 C6 -106.8(2) . . . . ?
C12 C11 N3 C7 -96.0(2) . . . . ?
C16 C11 N3 C7 82.1(2) . . . . ?
C8 C7 N3 C6 1.51(18) . . . . ?
C17 C7 N3 C6 -125.01(16) . . . . ?
C18 C7 N3 C6 127.15(17) . . . . ?
C8 C7 N3 C11 173.42(15) . . . . ?
C17 C7 N3 C11 46.9(2) . . . . ?
C18 C7 N3 C11 -60.9(2) . . . . ?
C13 C14 C20 O2 39.1(10) . . . . ?
C15 C14 C20 O2 -132.6(7) . . . . ?
C13 C14 C20 N5 -136.6(6) . . . . ?
C15 C14 C20 N5 51.8(8) . . . . ?
O2 C20 N5 C21 -2.4(12) . . . . ?
C14 C20 N5 C21 173.3(5) . . . . ?
C13 C14 C20D O2D 128.7(6) . . . . ?
C15 C14 C20D O2D -56.7(6) . . . . ?
C13 C14 C20D N5D -48.1(7) . . . . ?
C15 C14 C20D N5D 126.5(5) . . . . ?
O2D C20D N5D C21D 2.1(9) . . . . ?
C14 C20D N5D C21D 178.6(4) . . . . ?
O3 C23 C24 C25 -28.0(8) . . . . ?
C22 C23 C24 C25 -173.8(5) . . . . ?

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
_geom_hbond_publ_flag
N5 H5N O2 0.88 2.24 2.936(5) 136 4_586 yes
O3 H3O O2 0.84 2.10 2.699(5) 128 . yes
C24 H24A O2 0.99 1.59 2.491(7) 148 3_575 yes
C24 H24B F4 0.99 2.32 3.218(7) 150 1_554 yes

_refine_diff_density_max         0.544
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.131

####################################################################### 
# 
# 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_KB101_0m_APA-EtOH-2-1
_database_code_depnum_ccdc_archive 'CCDC 2152157'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-02-15 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            Apalutamide-Ethanol-2:1
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C21 H15 F4 N5 O2 S), C2 H6 O'
_chemical_formula_sum            'C44 H36 F8 N10 O5 S2'
_chemical_formula_weight         1000.95

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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 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, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   16.568(10)
_cell_length_b                   37.54(2)
_cell_length_c                   7.364(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4580(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5718
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      22.95

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             2056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.206
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4726
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27853
_diffrn_reflns_av_unetI/netI     0.0970
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.494
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8064
_reflns_number_gt                5112
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1186P)²+0.5342P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.45(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8064
_refine_ls_number_parameters     776
_refine_ls_number_restraints     562
_refine_ls_R_factor_all          0.1207
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.2143
_refine_ls_wR_factor_gt          0.1782
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.002
_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
C1A C 0.6106(4) 0.26475(17) 0.5465(10) 0.0370(17) Uani 1 1 d . . . . .
C2A C 0.5865(5) 0.24902(17) 0.3840(11) 0.0404(19) Uani 1 1 d . . . . .
H2A H 0.560611 0.262025 0.293733 0.048 Uiso 1 1 calc R U . . .
C3A C 0.6029(5) 0.21319(18) 0.3635(10) 0.0397(19) Uani 1 1 d . . . . .
C4A C 0.6408(5) 0.19494(17) 0.5017(11) 0.042(2) Uani 1 1 d . . . . .
C5A C 0.6459(5) 0.24467(17) 0.6801(12) 0.049(2) Uani 1 1 d . . . . .
H5A H 0.659521 0.255531 0.789402 0.058 Uiso 1 1 calc R U . . .
C6A C 0.6199(4) 0.32931(17) 0.4618(10) 0.0367(17) Uani 1 1 d . . . . .
C7A C 0.5458(5) 0.35458(17) 0.7032(10) 0.0400(18) Uani 1 1 d . . . . .
C8A C 0.5516(5) 0.31459(17) 0.7236(11) 0.0426(19) Uani 1 1 d . . . . .
C9A C 0.5746(6) 0.1949(2) 0.1896(13) 0.055(2) Uani 1 1 d D . . . .
C10A C 0.6622(6) 0.1578(2) 0.4879(14) 0.062(3) Uani 1 1 d . . . . .
C11A C 0.6085(5) 0.39387(17) 0.4635(10) 0.0373(18) Uani 1 1 d . . . . .
C12A C 0.6813(5) 0.40904(18) 0.4937(9) 0.0420(19) Uani 1 1 d . . . . .
H12A H 0.721457 0.396972 0.556863 0.050 Uiso 1 1 calc R U . . .
C13A C 0.6942(5) 0.44312(18) 0.4277(11) 0.0416(18) Uani 1 1 d . . . . .
C14A C 0.6384(5) 0.46262(18) 0.3328(11) 0.045(2) Uani 1 1 d . . . . .
C15A C 0.5669(5) 0.44610(19) 0.2994(12) 0.054(2) Uani 1 1 d . . . . .
H15A H 0.527840 0.457906 0.231572 0.064 Uiso 1 1 calc R U . . .
C16A C 0.5509(5) 0.41265(19) 0.3626(10) 0.047(2) Uani 1 1 d . . . . .
H16A H 0.501136 0.402217 0.338354 0.057 Uiso 1 1 calc R U . . .
C17A C 0.5716(5) 0.37578(19) 0.8744(10) 0.046(2) Uani 1 1 d . . . . .
H17A H 0.601897 0.361871 0.962069 0.056 Uiso 1 1 calc R U . . .
H17B H 0.598565 0.398135 0.847902 0.056 Uiso 1 1 calc R U . . .
C18A C 0.4586(5) 0.3690(2) 0.7249(11) 0.054(2) Uani 1 1 d . . . . .
H18A H 0.446018 0.388990 0.646362 0.064 Uiso 1 1 calc R U . . .
H18B H 0.417139 0.350801 0.718345 0.064 Uiso 1 1 calc R U . . .
C19A C 0.4820(6) 0.3797(2) 0.9199(13) 0.067(3) Uani 1 1 d . . . . .
H19A H 0.466565 0.403853 0.951274 0.081 Uiso 1 1 calc R U . . .
H19B H 0.463438 0.363008 1.011379 0.081 Uiso 1 1 calc R U . . .
C20A C 0.6493(6) 0.5002(2) 0.2703(13) 0.056(2) Uani 1 1 d . . . . .
C21A C 0.6999(15) 0.5599(4) 0.326(4) 0.089(8) Uani 0.57(3) 1 d D U P A 1
H21A H 0.722834 0.561606 0.206458 0.133 Uiso 0.57(3) 1 calc R U P A 1
H21B H 0.735962 0.570582 0.412249 0.133 Uiso 0.57(3) 1 calc R U P A 1
H21C H 0.649035 0.572087 0.328507 0.133 Uiso 0.57(3) 1 calc R U P A 1
N5A N 0.6878(13) 0.5224(4) 0.372(4) 0.068(6) Uani 0.57(3) 1 d D U P A 1
H5NA H 0.707350 0.514781 0.473164 0.082 Uiso 0.57(3) 1 calc R U P A 1
C211 C 0.738(3) 0.5534(7) 0.221(5) 0.101(10) Uani 0.43(3) 1 d D U P A 2
H21D H 0.786417 0.554035 0.148363 0.151 Uiso 0.43(3) 1 calc R U P A 2
H21E H 0.744483 0.568816 0.323689 0.151 Uiso 0.43(3) 1 calc R U P A 2
H21F H 0.693229 0.561280 0.148919 0.151 Uiso 0.43(3) 1 calc R U P A 2
N51 N 0.723(2) 0.5161(6) 0.284(4) 0.074(7) Uani 0.43(3) 1 d D U P A 2
H5N1 H 0.762694 0.504312 0.331397 0.088 Uiso 0.43(3) 1 calc R U P A 2
N1A N 0.6613(4) 0.21034(16) 0.6587(10) 0.0525(18) Uani 1 1 d . . . . .
N2A N 0.5943(4) 0.30170(13) 0.5775(8) 0.0370(15) Uani 1 1 d . . . . .
N3A N 0.5905(4) 0.35952(14) 0.5335(8) 0.0394(15) Uani 1 1 d . . . . .
N4A N 0.6762(6) 0.1282(2) 0.4858(15) 0.096(3) Uani 1 1 d . . . . .
S1A S 0.67675(13) 0.32463(5) 0.2812(3) 0.0482(6) Uani 1 1 d . . . . .
F1A F 0.5523(14) 0.2188(3) 0.0585(16) 0.078(4) Uani 0.68(4) 1 d D U P B 3
F2A F 0.5091(9) 0.1763(5) 0.219(3) 0.086(5) Uani 0.68(4) 1 d D U P B 3
F3A F 0.6256(7) 0.1734(5) 0.114(3) 0.082(5) Uani 0.68(4) 1 d D U P B 3
F11 F 0.601(3) 0.2139(8) 0.061(4) 0.094(9) Uani 0.32(4) 1 d D U P B 4
F21 F 0.4985(12) 0.1899(11) 0.195(5) 0.071(8) Uani 0.32(4) 1 d D U P B 4
F31 F 0.607(2) 0.1625(7) 0.181(5) 0.084(8) Uani 0.32(4) 1 d D U P B 4
F4A F 0.7710(3) 0.45643(12) 0.4503(8) 0.0652(14) Uani 1 1 d . . . . .
O1A O 0.5223(4) 0.29674(14) 0.8454(9) 0.0675(18) Uani 1 1 d . . . . .
O2A O 0.6056(6) 0.51144(18) 0.1495(13) 0.112(3) Uani 1 1 d . . . . .
C1B C 0.8441(4) 0.26408(16) 1.0412(10) 0.0379(18) Uani 1 1 d . . . . .
C2B C 0.8637(5) 0.24824(17) 0.8803(10) 0.0396(18) Uani 1 1 d . . . . .
H2B H 0.886507 0.261676 0.787347 0.047 Uiso 1 1 calc R U . . .
C3B C 0.8498(5) 0.21206(18) 0.8550(10) 0.0415(19) Uani 1 1 d . . . . .
C4B C 0.8121(5) 0.19441(18) 0.9956(12) 0.049(2) Uani 1 1 d . . . . .
C5B C 0.8063(5) 0.24400(18) 1.1755(11) 0.050(2) Uani 1 1 d . . . . .
H5B H 0.791677 0.255079 1.283536 0.060 Uiso 1 1 calc R U . . .
C6B C 0.8321(4) 0.32854(16) 0.9581(10) 0.0360(17) Uani 1 1 d . . . . .
C7B C 0.9095(5) 0.35324(18) 1.1991(10) 0.0422(18) Uani 1 1 d . . . . .
C8B C 0.9050(5) 0.31333(18) 1.2198(11) 0.048(2) Uani 1 1 d . . . . .
C9B C 0.8772(5) 0.1945(2) 0.6852(12) 0.051(2) Uani 1 1 d D . . . .
C10B C 0.7913(6) 0.1567(2) 0.9852(13) 0.063(3) Uani 1 1 d . . . . .
C11B C 0.8461(5) 0.39378(18) 0.9603(11) 0.044(2) Uani 1 1 d . . . . .
C12B C 0.9037(5) 0.41006(19) 0.8562(11) 0.049(2) Uani 1 1 d . . . . .
H12B H 0.950933 0.398447 0.822406 0.059 Uiso 1 1 calc R U . . .
C13B C 0.8876(6) 0.4450(2) 0.8038(13) 0.059(2) Uani 1 1 d . . . . .
C14B C 0.8180(6) 0.46304(19) 0.8514(11) 0.051(2) Uani 1 1 d . . . . .
C15B C 0.7594(6) 0.4446(2) 0.9460(12) 0.054(2) Uani 1 1 d . . . . .
H15B H 0.709820 0.455280 0.969520 0.064 Uiso 1 1 calc R U . . .
C16B C 0.7741(5) 0.4103(2) 1.0058(11) 0.048(2) Uani 1 1 d . . . . .
H16B H 0.735991 0.398411 1.075980 0.057 Uiso 1 1 calc R U . . .
C17B C 0.9965(5) 0.3671(2) 1.2148(12) 0.056(2) Uani 1 1 d . . . . .
H17C H 1.008992 0.386372 1.131902 0.067 Uiso 1 1 calc R U . . .
H17D H 1.037129 0.348487 1.208727 0.067 Uiso 1 1 calc R U . . .
C18B C 0.8865(5) 0.3746(2) 1.3703(11) 0.052(2) Uani 1 1 d . . . . .
H18C H 0.858316 0.396682 1.344789 0.062 Uiso 1 1 calc R U . . .
H18D H 0.858177 0.360707 1.461275 0.062 Uiso 1 1 calc R U . . .
C19B C 0.9768(6) 0.3794(3) 1.4094(13) 0.073(3) Uani 1 1 d . . . . .
H19C H 0.997263 0.363576 1.502839 0.088 Uiso 1 1 calc R U . . .
H19D H 0.992155 0.403876 1.433815 0.088 Uiso 1 1 calc R U . . .
N1B N 0.7904(5) 0.20917(16) 1.1543(10) 0.0541(19) Uani 1 1 d . . . . .
N2B N 0.8583(4) 0.30085(13) 1.0717(8) 0.0381(15) Uani 1 1 d . . . . .
N3B N 0.8632(4) 0.35899(14) 1.0292(8) 0.0399(15) Uani 1 1 d . . . . .
N4B N 0.7726(6) 0.12757(19) 0.9794(15) 0.097(3) Uani 1 1 d . . . . .
S1B S 0.77577(13) 0.32429(5) 0.7779(3) 0.0483(6) Uani 1 1 d . . . . .
C20B C 0.8045(7) 0.5012(2) 0.8005(15) 0.066(3) Uani 0.658(13) 1 d D . P C 5
C21B C 0.8608(12) 0.5628(4) 0.781(3) 0.122(7) Uani 0.658(13) 1 d D U P C 5
H21G H 0.881593 0.569995 0.665124 0.183 Uiso 0.658(13) 1 calc R U P C 5
H21H H 0.892999 0.573092 0.875856 0.183 Uiso 0.658(13) 1 calc R U P C 5
H21I H 0.805984 0.570793 0.793051 0.183 Uiso 0.658(13) 1 calc R U P C 5
O2B O 0.7370(15) 0.5108(5) 0.749(4) 0.092(6) Uani 0.658(13) 1 d D U P C 5
N5B N 0.863(2) 0.5228(6) 0.796(4) 0.094(7) Uani 0.658(13) 1 d D U P C 5
H5NB H 0.910772 0.513486 0.801329 0.113 Uiso 0.658(13) 1 calc R U P C 5
C202 C 0.8045(7) 0.5012(2) 0.8005(15) 0.066(3) Uani 0.342(13) 1 d D U P C 6
C212 C 0.7088(17) 0.5506(5) 0.746(4) 0.084(8) Uani 0.342(13) 1 d D U P C 6
H21J H 0.690540 0.555713 0.624834 0.125 Uiso 0.342(13) 1 calc R U P C 6
H21K H 0.754501 0.565376 0.773778 0.125 Uiso 0.342(13) 1 calc R U P C 6
H21L H 0.666152 0.555388 0.830510 0.125 Uiso 0.342(13) 1 calc R U P C 6
O22 O 0.859(3) 0.5218(10) 0.857(5) 0.072(8) Uani 0.342(13) 1 d D U P C 6
N52 N 0.733(3) 0.5123(9) 0.759(9) 0.093(12) Uani 0.342(13) 1 d D U P C 6
H5N2 H 0.696332 0.496524 0.736487 0.112 Uiso 0.342(13) 1 calc R U P C 6
F1B F 0.9011(15) 0.2182(3) 0.5563(19) 0.084(5) Uani 0.67(4) 1 d D U P D 5
F2B F 0.9464(8) 0.1770(5) 0.710(2) 0.076(4) Uani 0.67(4) 1 d D U P D 5
F3B F 0.8261(8) 0.1746(6) 0.600(3) 0.096(6) Uani 0.67(4) 1 d D U P D 5
F12 F 0.853(3) 0.2118(8) 0.546(3) 0.084(8) Uani 0.33(4) 1 d D U P D 6
F22 F 0.9542(13) 0.1906(11) 0.683(6) 0.090(9) Uani 0.33(4) 1 d D U P D 6
F32 F 0.847(2) 0.1622(6) 0.672(4) 0.082(8) Uani 0.33(4) 1 d D U P D 6
F4B F 0.9423(4) 0.46058(14) 0.6938(10) 0.103(2) Uani 1 1 d . . . . .
O1B O 0.9328(4) 0.29499(13) 1.3355(8) 0.0670(18) Uani 1 1 d . . . . .
O3A O 0.4289(13) 0.5249(6) -0.191(4) 0.123(7) Uani 0.5 1 d D U P E -7
H1O H 0.418673 0.546041 -0.207774 0.185 Uiso 0.5 1 calc R U P E -7
C22A C 0.512(3) 0.4765(12) -0.228(6) 0.146(13) Uani 0.5 1 d D U P E -7
H22A H 0.505064 0.461161 -0.331105 0.218 Uiso 0.5 1 calc R U P E -7
H22B H 0.471978 0.470643 -0.137612 0.218 Uiso 0.5 1 calc R U P E -7
H22C H 0.564679 0.473377 -0.177965 0.218 Uiso 0.5 1 calc R U P E -7
C23A C 0.501(3) 0.5156(12) -0.287(6) 0.170(16) Uani 0.5 1 d D U P E -7
H23A H 0.545963 0.530269 -0.250275 0.204 Uiso 0.5 1 calc R U P E -7
H23B H 0.493224 0.517608 -0.417515 0.204 Uiso 0.5 1 calc R U P E -7
C22B C 1.008(3) 0.5046(12) 1.039(3) 0.114(8) Uani 0.25 1 d D U P F -8
H22D H 1.050268 0.515418 0.970511 0.171 Uiso 0.25 1 calc R U P F -8
H22E H 1.017466 0.479505 1.050260 0.171 Uiso 0.25 1 calc R U P F -8
H22F H 0.957052 0.508429 0.978800 0.171 Uiso 0.25 1 calc R U P F -8
C23B C 1.005(5) 0.5212(19) 1.227(6) 0.136(13) Uani 0.25 1 d D U P F -8
H23C H 1.054562 0.517387 1.292716 0.164 Uiso 0.25 1 calc R U P F -8
H23D H 0.993616 0.546566 1.220625 0.164 Uiso 0.25 1 calc R U P F -8
O3B O 0.941(3) 0.5031(15) 1.307(5) 0.157(13) Uani 0.25 1 d D U P F -8
H2O H 0.898784 0.509530 1.260710 0.236 Uiso 0.25 1 calc R U P F -8
C222 C 1.008(3) 0.5046(12) 1.039(3) 0.114(8) Uani 0.25 1 d D U P G -9
H22G H 1.057354 0.491986 1.021438 0.171 Uiso 0.25 1 calc R U P G -9
H22H H 0.963871 0.491103 0.988805 0.171 Uiso 0.25 1 calc R U P G -9
H22I H 1.010574 0.527387 0.980477 0.171 Uiso 0.25 1 calc R U P G -9
C232 C 0.993(4) 0.510(2) 1.242(4) 0.138(13) Uani 0.25 1 d D U P G -9
H23E H 0.989522 0.487282 1.304436 0.166 Uiso 0.25 1 calc R U P G -9
H23F H 1.036569 0.523834 1.296048 0.166 Uiso 0.25 1 calc R U P G -9
O32 O 0.921(3) 0.5281(14) 1.250(6) 0.170(13) Uani 0.25 1 d D U P G -9
H202 H 0.929997 0.549394 1.266088 0.254 Uiso 0.25 1 calc R U P G -9


_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
C1A C5A 1.371(10) . ?
C1A C2A 1.393(10) . ?
C1A N2A 1.432(8) . ?
C2A C3A 1.380(9) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.378(10) . ?
C3A C9A 1.527(11) . ?
C4A N1A 1.337(10) . ?
C4A C10A 1.441(10) . ?
C5A N1A 1.323(9) . ?
C5A H5A 0.9300 . ?
C6A N3A 1.342(8) . ?
C6A N2A 1.407(9) . ?
C6A S1A 1.639(8) . ?
C7A N3A 1.464(10) . ?
C7A C8A 1.512(9) . ?
C7A C17A 1.551(10) . ?
C7A C18A 1.552(11) . ?
C8A O1A 1.220(9) . ?
C8A N2A 1.375(9) . ?
C9A F11 1.26(2) . ?
C9A F21 1.28(2) . ?
C9A F3A 1.293(12) . ?
C9A F2A 1.309(14) . ?
C9A F31 1.33(2) . ?
C9A F1A 1.370(13) . ?
C10A N4A 1.135(10) . ?
C11A C12A 1.352(10) . ?
C11A C16A 1.400(10) . ?
C11A N3A 1.420(9) . ?
C12A C13A 1.385(10) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.370(11) . ?
C13A F4A 1.378(9) . ?
C14A C15A 1.360(12) . ?
C14A C20A 1.493(10) . ?
C15A C16A 1.365(10) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C17A C19A 1.529(12) . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C18A C19A 1.541(12) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C20A O2A 1.223(11) . ?
C20A N5A 1.29(2) . ?
C20A N51 1.37(3) . ?
C21A N5A 1.461(17) . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
N5A H5NA 0.8600 . ?
C211 N51 1.50(2) . ?
C211 H21D 0.9600 . ?
C211 H21E 0.9600 . ?
C211 H21F 0.9600 . ?
N51 H5N1 0.8600 . ?
C1B C2B 1.366(10) . ?
C1B C5B 1.392(10) . ?
C1B N2B 1.418(8) . ?
C2B C3B 1.390(9) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.378(11) . ?
C3B C9B 1.484(11) . ?
C4B N1B 1.343(10) . ?
C4B C10B 1.460(11) . ?
C5B N1B 1.343(9) . ?
C5B H5B 0.9300 . ?
C6B N3B 1.359(8) . ?
C6B N2B 1.403(9) . ?
C6B S1B 1.630(8) . ?
C7B N3B 1.483(10) . ?
C7B C8B 1.508(10) . ?
C7B C17B 1.537(11) . ?
C7B C18B 1.541(10) . ?
C8B O1B 1.188(9) . ?
C8B N2B 1.417(10) . ?
C9B F12 1.280(18) . ?
C9B F22 1.29(2) . ?
C9B F3B 1.291(13) . ?
C9B F32 1.318(18) . ?
C9B F2B 1.335(13) . ?
C9B F1B 1.360(13) . ?
C10B N4B 1.136(10) . ?
C11B C12B 1.368(11) . ?
C11B C16B 1.385(11) . ?
C11B N3B 1.429(9) . ?
C12B C13B 1.392(10) . ?
C12B H12B 0.9300 . ?
C13B F4B 1.349(10) . ?
C13B C14B 1.383(12) . ?
C14B C15B 1.382(12) . ?
C14B C202 1.496(11) . ?
C14B C20B 1.496(11) . ?
C15B C16B 1.382(10) . ?
C15B H15B 0.9300 . ?
C16B H16B 0.9300 . ?
C17B C19B 1.542(12) . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?
C18B C19B 1.535(13) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C20B O2B 1.24(2) . ?
C20B N5B 1.27(3) . ?
C21B N5B 1.50(2) . ?
C21B H21G 0.9600 . ?
C21B H21H 0.9600 . ?
C21B H21I 0.9600 . ?
N5B H5NB 0.8600 . ?
C202 O22 1.26(5) . ?
C202 N52 1.30(4) . ?
C212 N52 1.50(3) . ?
C212 H21J 0.9600 . ?
C212 H21K 0.9600 . ?
C212 H21L 0.9600 . ?
N52 H5N2 0.8600 . ?
O3A C23A 1.43(3) . ?
O3A H1O 0.8200 . ?
C22A C23A 1.54(2) . ?
C22A H22A 0.9600 . ?
C22A H22B 0.9600 . ?
C22A H22C 0.9600 . ?
C23A H23A 0.9700 . ?
C23A H23B 0.9700 . ?
C22B C23B 1.52(3) . ?
C22B H22D 0.9600 . ?
C22B H22E 0.9600 . ?
C22B H22F 0.9600 . ?
C23B O3B 1.38(3) . ?
C23B H23C 0.9700 . ?
C23B H23D 0.9700 . ?
O3B H2O 0.8200 . ?
C222 C232 1.52(3) . ?
C222 H22G 0.9599 . ?
C222 H22H 0.9600 . ?
C222 H22I 0.9601 . ?
C232 O32 1.38(3) . ?
C232 H23E 0.9700 . ?
C232 H23F 0.9700 . ?
O32 H202 0.8200 . ?

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
C5A C1A C2A 120.4(6) . . ?
C5A C1A N2A 119.9(6) . . ?
C2A C1A N2A 119.6(7) . . ?
C3A C2A C1A 116.8(7) . . ?
C3A C2A H2A 121.6 . . ?
C1A C2A H2A 121.6 . . ?
C4A C3A C2A 119.6(7) . . ?
C4A C3A C9A 122.4(6) . . ?
C2A C3A C9A 118.0(7) . . ?
N1A C4A C3A 122.6(6) . . ?
N1A C4A C10A 114.6(7) . . ?
C3A C4A C10A 122.7(7) . . ?
N1A C5A C1A 122.2(7) . . ?
N1A C5A H5A 118.9 . . ?
C1A C5A H5A 118.9 . . ?
N3A C6A N2A 105.9(6) . . ?
N3A C6A S1A 128.2(6) . . ?
N2A C6A S1A 125.8(5) . . ?
N3A C7A C8A 100.3(6) . . ?
N3A C7A C17A 119.3(6) . . ?
C8A C7A C17A 114.3(6) . . ?
N3A C7A C18A 121.0(6) . . ?
C8A C7A C18A 113.3(7) . . ?
C17A C7A C18A 89.7(6) . . ?
O1A C8A N2A 125.9(6) . . ?
O1A C8A C7A 126.4(7) . . ?
N2A C8A C7A 107.7(6) . . ?
F11 C9A F21 116.2(19) . . ?
F3A C9A F2A 106.2(10) . . ?
F11 C9A F31 110.1(17) . . ?
F21 C9A F31 105.2(16) . . ?
F3A C9A F1A 106.4(11) . . ?
F2A C9A F1A 103.9(10) . . ?
F11 C9A C3A 105.8(15) . . ?
F21 C9A C3A 110.3(17) . . ?
F3A C9A C3A 116.1(9) . . ?
F2A C9A C3A 111.0(11) . . ?
F31 C9A C3A 109.2(16) . . ?
F1A C9A C3A 112.3(7) . . ?
N4A C10A C4A 175.9(12) . . ?
C12A C11A C16A 118.9(7) . . ?
C12A C11A N3A 120.7(7) . . ?
C16A C11A N3A 120.4(7) . . ?
C11A C12A C13A 118.0(7) . . ?
C11A C12A H12A 121.0 . . ?
C13A C12A H12A 121.0 . . ?
C14A C13A F4A 119.4(7) . . ?
C14A C13A C12A 124.6(8) . . ?
F4A C13A C12A 115.8(7) . . ?
C15A C14A C13A 115.8(7) . . ?
C15A C14A C20A 118.7(8) . . ?
C13A C14A C20A 125.4(8) . . ?
C14A C15A C16A 121.8(8) . . ?
C14A C15A H15A 119.1 . . ?
C16A C15A H15A 119.1 . . ?
C15A C16A C11A 120.8(8) . . ?
C15A C16A H16A 119.6 . . ?
C11A C16A H16A 119.6 . . ?
C19A C17A C7A 87.7(6) . . ?
C19A C17A H17A 114.0 . . ?
C7A C17A H17A 114.0 . . ?
C19A C17A H17B 114.0 . . ?
C7A C17A H17B 114.0 . . ?
H17A C17A H17B 111.2 . . ?
C19A C18A C7A 87.3(6) . . ?
C19A C18A H18A 114.1 . . ?
C7A C18A H18A 114.1 . . ?
C19A C18A H18B 114.1 . . ?
C7A C18A H18B 114.1 . . ?
H18A C18A H18B 111.3 . . ?
C17A C19A C18A 90.9(7) . . ?
C17A C19A H19A 113.5 . . ?
C18A C19A H19A 113.5 . . ?
C17A C19A H19B 113.5 . . ?
C18A C19A H19B 113.5 . . ?
H19A C19A H19B 110.8 . . ?
O2A C20A N5A 119.4(10) . . ?
O2A C20A N51 115.8(12) . . ?
O2A C20A C14A 118.6(9) . . ?
N5A C20A C14A 119.4(11) . . ?
N51 C20A C14A 119.9(13) . . ?
N5A C21A H21A 109.5 . . ?
N5A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
N5A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C20A N5A C21A 123.7(17) . . ?
C20A N5A H5NA 118.1 . . ?
C21A N5A H5NA 118.1 . . ?
N51 C211 H21D 109.5 . . ?
N51 C211 H21E 109.5 . . ?
H21D C211 H21E 109.5 . . ?
N51 C211 H21F 109.5 . . ?
H21D C211 H21F 109.5 . . ?
H21E C211 H21F 109.5 . . ?
C20A N51 C211 122(2) . . ?
C20A N51 H5N1 118.9 . . ?
C211 N51 H5N1 118.9 . . ?
C5A N1A C4A 118.4(7) . . ?
C8A N2A C6A 111.7(5) . . ?
C8A N2A C1A 124.3(6) . . ?
C6A N2A C1A 124.0(6) . . ?
C6A N3A C11A 123.2(6) . . ?
C6A N3A C7A 114.3(6) . . ?
C11A N3A C7A 122.1(5) . . ?
C2B C1B C5B 119.2(6) . . ?
C2B C1B N2B 121.4(6) . . ?
C5B C1B N2B 119.3(7) . . ?
C1B C2B C3B 120.1(7) . . ?
C1B C2B H2B 119.9 . . ?
C3B C2B H2B 119.9 . . ?
C4B C3B C2B 116.4(7) . . ?
C4B C3B C9B 123.9(6) . . ?
C2B C3B C9B 119.7(7) . . ?
N1B C4B C3B 125.2(7) . . ?
N1B C4B C10B 112.5(8) . . ?
C3B C4B C10B 122.3(8) . . ?
N1B C5B C1B 122.2(7) . . ?
N1B C5B H5B 118.9 . . ?
C1B C5B H5B 118.9 . . ?
N3B C6B N2B 106.0(6) . . ?
N3B C6B S1B 127.8(5) . . ?
N2B C6B S1B 126.2(5) . . ?
N3B C7B C8B 101.8(6) . . ?
N3B C7B C17B 120.0(7) . . ?
C8B C7B C17B 112.0(7) . . ?
N3B C7B C18B 119.1(6) . . ?
C8B C7B C18B 115.0(7) . . ?
C17B C7B C18B 89.7(6) . . ?
O1B C8B N2B 124.9(6) . . ?
O1B C8B C7B 129.0(8) . . ?
N2B C8B C7B 106.1(6) . . ?
F12 C9B F22 111.1(19) . . ?
F12 C9B F32 106.8(15) . . ?
F22 C9B F32 106.1(16) . . ?
F3B C9B F2B 110.0(10) . . ?
F3B C9B F1B 103.3(11) . . ?
F2B C9B F1B 99.7(10) . . ?
F12 C9B C3B 110.8(13) . . ?
F22 C9B C3B 111(2) . . ?
F3B C9B C3B 117.7(10) . . ?
F32 C9B C3B 110.5(12) . . ?
F2B C9B C3B 111.5(10) . . ?
F1B C9B C3B 112.8(8) . . ?
N4B C10B C4B 177.8(11) . . ?
C12B C11B C16B 122.4(7) . . ?
C12B C11B N3B 118.0(7) . . ?
C16B C11B N3B 119.6(7) . . ?
C11B C12B C13B 116.3(8) . . ?
C11B C12B H12B 121.9 . . ?
C13B C12B H12B 121.9 . . ?
F4B C13B C14B 119.9(7) . . ?
F4B C13B C12B 116.6(8) . . ?
C14B C13B C12B 123.4(8) . . ?
C15B C14B C13B 118.0(7) . . ?
C15B C14B C202 120.0(8) . . ?
C13B C14B C202 122.1(8) . . ?
C15B C14B C20B 120.0(8) . . ?
C13B C14B C20B 122.1(8) . . ?
C14B C15B C16B 120.2(8) . . ?
C14B C15B H15B 119.9 . . ?
C16B C15B H15B 119.9 . . ?
C15B C16B C11B 119.5(8) . . ?
C15B C16B H16B 120.3 . . ?
C11B C16B H16B 120.3 . . ?
C7B C17B C19B 88.4(7) . . ?
C7B C17B H17C 113.9 . . ?
C19B C17B H17C 113.9 . . ?
C7B C17B H17D 113.9 . . ?
C19B C17B H17D 113.9 . . ?
H17C C17B H17D 111.1 . . ?
C19B C18B C7B 88.5(6) . . ?
C19B C18B H18C 113.9 . . ?
C7B C18B H18C 113.9 . . ?
C19B C18B H18D 113.9 . . ?
C7B C18B H18D 113.9 . . ?
H18C C18B H18D 111.1 . . ?
C18B C19B C17B 89.8(7) . . ?
C18B C19B H19C 113.7 . . ?
C17B C19B H19C 113.7 . . ?
C18B C19B H19D 113.7 . . ?
C17B C19B H19D 113.7 . . ?
H19C C19B H19D 110.9 . . ?
C4B N1B C5B 116.7(7) . . ?
C6B N2B C8B 112.5(5) . . ?
C6B N2B C1B 125.1(6) . . ?
C8B N2B C1B 122.3(6) . . ?
C6B N3B C11B 123.8(6) . . ?
C6B N3B C7B 113.5(5) . . ?
C11B N3B C7B 122.3(6) . . ?
O2B C20B N5B 119.9(15) . . ?
O2B C20B C14B 119.6(14) . . ?
N5B C20B C14B 120.2(16) . . ?
N5B C21B H21G 109.5 . . ?
N5B C21B H21H 109.5 . . ?
H21G C21B H21H 109.5 . . ?
N5B C21B H21I 109.5 . . ?
H21G C21B H21I 109.5 . . ?
H21H C21B H21I 109.5 . . ?
C20B N5B C21B 128(3) . . ?
C20B N5B H5NB 115.9 . . ?
C21B N5B H5NB 115.9 . . ?
O22 C202 N52 122(2) . . ?
O22 C202 C14B 113.6(17) . . ?
N52 C202 C14B 120.4(19) . . ?
N52 C212 H21J 109.5 . . ?
N52 C212 H21K 109.5 . . ?
H21J C212 H21K 109.5 . . ?
N52 C212 H21L 109.5 . . ?
H21J C212 H21L 109.5 . . ?
H21K C212 H21L 109.5 . . ?
C202 N52 C212 125(4) . . ?
C202 N52 H5N2 117.7 . . ?
C212 N52 H5N2 117.7 . . ?
C23A O3A H1O 109.5 . . ?
C23A C22A H22A 109.5 . . ?
C23A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C23A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
O3A C23A C22A 101(2) . . ?
O3A C23A H23A 111.6 . . ?
C22A C23A H23A 111.6 . . ?
O3A C23A H23B 111.6 . . ?
C22A C23A H23B 111.6 . . ?
H23A C23A H23B 109.4 . . ?
C23B C22B H22D 109.5 . . ?
C23B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C23B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
O3B C23B C22B 102(2) . . ?
O3B C23B H23C 111.3 . . ?
C22B C23B H23C 111.3 . . ?
O3B C23B H23D 111.3 . . ?
C22B C23B H23D 111.3 . . ?
H23C C23B H23D 109.2 . . ?
C23B O3B H2O 109.5 . . ?
C232 C222 H22G 109.5 . . ?
C232 C222 H22H 109.5 . . ?
H22G C222 H22H 109.5 . . ?
C232 C222 H22I 109.5 . . ?
H22G C222 H22I 109.5 . . ?
H22H C222 H22I 109.5 . . ?
O32 C232 C222 104(3) . . ?
O32 C232 H23E 111.0 . . ?
C222 C232 H23E 111.0 . . ?
O32 C232 H23F 111.0 . . ?
C222 C232 H23F 111.0 . . ?
H23E C232 H23F 109.0 . . ?
C232 O32 H202 109.5 . . ?

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
_geom_hbond_publ_flag
N5A H5NA O2B 0.86 2.10 2.93(4) 162 . yes
C15A H15A O2A 0.93 2.56 3.454(13) 160 2_665 yes
C19B H19C F2A 0.97 2.54 3.49(2) 163 4_557 yes
C22A H22B O2A 0.96 2.56 3.43(5) 149 2_665 yes

_refine_diff_density_max         0.557
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_KB22_0m_APA-ACN-1-1
_database_code_depnum_ccdc_archive 'CCDC 2152156'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-02-15 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            Apalutamide-Acetonitrile-1:1
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 F4 N5 O2 S, C2 H3 N'
_chemical_formula_sum            'C23 H18 F4 N6 O2 S'
_chemical_formula_weight         518.49

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.9856(4)
_cell_length_b                   15.2222(6)
_cell_length_c                   16.9653(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2320.52(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9793
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      30.46

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.206
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36626
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.401
_diffrn_reflns_theta_max         30.468
_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 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6979
_reflns_number_gt                6697
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_max     0.977
_reflns_Friedel_fraction_full    0.994

_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0371P)²+0.3003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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_abs_structure_details 
;
 Flack x determined using 3043 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6979
_refine_ls_number_parameters     330
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0707
_refine_ls_wR_factor_gt          0.0695
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.050
_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
C1 C 0.41230(16) 0.27254(10) 0.69064(9) 0.0120(3) Uani 1 1 d . . . . .
F2 F 0.55416(12) 0.25094(8) 0.94597(7) 0.0238(2) Uani 1 1 d . . . . .
C2 C 0.50109(16) 0.29939(10) 0.75295(9) 0.0128(3) Uani 1 1 d . . . . .
H2 H 0.531413 0.358905 0.758091 0.015 Uiso 1 1 calc R U . . .
F3 F 0.67546(14) 0.34605(7) 0.87709(7) 0.0277(2) Uani 1 1 d . . . . .
C3 C 0.54440(16) 0.23631(10) 0.80777(9) 0.0121(3) Uani 1 1 d . . . . .
F4 F 0.07979(11) 0.40767(7) 0.27147(6) 0.0181(2) Uani 1 1 d . . . . .
C4 C 0.49959(16) 0.14972(10) 0.79598(9) 0.0126(3) Uani 1 1 d . . . . .
C5 C 0.36658(17) 0.18513(10) 0.68564(9) 0.0140(3) Uani 1 1 d . . . . .
H5 H 0.301336 0.168579 0.644158 0.017 Uiso 1 1 calc R U . . .
C6 C 0.39485(16) 0.32936(10) 0.55308(9) 0.0129(3) Uani 1 1 d . . . . .
C7 C 0.25951(16) 0.45878(10) 0.57602(9) 0.0120(3) Uani 1 1 d . . . . .
C8 C 0.29136(15) 0.41277(10) 0.65304(9) 0.0118(3) Uani 1 1 d . . . . .
C9 C 0.63245(17) 0.26204(10) 0.87979(10) 0.0151(3) Uani 1 1 d . . . . .
C10 C 0.54786(17) 0.08063(10) 0.84904(10) 0.0155(3) Uani 1 1 d . . . . .
C11 C 0.33314(17) 0.41580(10) 0.43596(9) 0.0127(3) Uani 1 1 d . . . . .
C12 C 0.20397(17) 0.40212(10) 0.39238(9) 0.0135(3) Uani 1 1 d . . . . .
H12 H 0.115743 0.381362 0.416984 0.016 Uiso 1 1 calc R U . . .
C13 C 0.20720(17) 0.41944(10) 0.31255(9) 0.0131(3) Uani 1 1 d . . . . .
C14 C 0.33389(17) 0.44869(10) 0.27355(9) 0.0114(2) Uani 1 1 d . . . . .
C15 C 0.46156(17) 0.46316(10) 0.31912(9) 0.0137(3) Uani 1 1 d . . . . .
H15 H 0.549453 0.484283 0.294436 0.016 Uiso 1 1 calc R U . . .
C16 C 0.46200(16) 0.44715(11) 0.39988(9) 0.0143(3) Uani 1 1 d . . . . .
H16 H 0.549251 0.457479 0.430115 0.017 Uiso 1 1 calc R U . . .
C17 C 0.30091(18) 0.55762(10) 0.57538(10) 0.0160(3) Uani 1 1 d . . . . .
H17A H 0.335330 0.579310 0.523477 0.019 Uiso 1 1 calc R U . . .
H17B H 0.370690 0.574905 0.617794 0.019 Uiso 1 1 calc R U . . .
C18 C 0.09272(17) 0.48577(11) 0.56815(10) 0.0157(3) Uani 1 1 d . . . . .
H18A H 0.053755 0.482005 0.513668 0.019 Uiso 1 1 calc R U . . .
H18B H 0.025921 0.455415 0.605721 0.019 Uiso 1 1 calc R U . . .
C19 C 0.1359(2) 0.57927(12) 0.59355(12) 0.0231(3) Uani 1 1 d . . . . .
H19A H 0.116272 0.591702 0.649883 0.028 Uiso 1 1 calc R U . . .
H19B H 0.093652 0.625841 0.559504 0.028 Uiso 1 1 calc R U . . .
C20 C 0.33883(16) 0.46816(10) 0.18665(9) 0.0121(3) Uani 1 1 d . . . . .
C21 C 0.2711(2) 0.42075(14) 0.05433(11) 0.0230(4) Uani 1 1 d . . . . .
H21A H 0.369037 0.404480 0.033574 0.035 Uiso 1 1 calc R U . . .
H21B H 0.249695 0.482088 0.040910 0.035 Uiso 1 1 calc R U . . .
H21C H 0.194879 0.382663 0.031073 0.035 Uiso 1 1 calc R U . . .
S1 S 0.49689(5) 0.25174(3) 0.51184(3) 0.02024(9) Uani 1 1 d . . . . .
O1 O 0.25842(13) 0.43584(8) 0.71866(7) 0.0157(2) Uani 1 1 d . . . . .
O2 O 0.40619(13) 0.53272(8) 0.16166(7) 0.0160(2) Uani 1 1 d . . . . .
N1 N 0.41075(15) 0.12386(9) 0.73674(8) 0.0147(2) Uani 1 1 d . . . . .
F1 F 0.75644(10) 0.21391(8) 0.88765(7) 0.0211(2) Uani 1 1 d . . . . .
N2 N 0.36316(14) 0.33440(9) 0.63375(8) 0.0118(2) Uani 1 1 d . . . . .
N3 N 0.32942(15) 0.39945(8) 0.51896(8) 0.0129(2) Uani 1 1 d . . . . .
N4 N 0.58846(16) 0.02683(10) 0.89099(9) 0.0196(3) Uani 1 1 d . . . . .
N5 N 0.27042(17) 0.41041(10) 0.13952(9) 0.0183(3) Uani 1 1 d . . . . .
H5N H 0.229(3) 0.3648(18) 0.1598(16) 0.027 Uiso 1 1 d . U . . .
C22 C 0.2752(2) 0.18089(14) 0.33234(15) 0.0332(5) Uani 1 1 d . . . . .
H22A H 0.302149 0.118606 0.329077 0.050 Uiso 1 1 calc R U . . .
H22B H 0.207547 0.189982 0.376890 0.050 Uiso 1 1 calc R U . . .
H22C H 0.365364 0.216135 0.340003 0.050 Uiso 1 1 calc R U . . .
C23 C 0.2020(3) 0.20754(13) 0.25967(14) 0.0301(4) Uani 1 1 d . . . . .
N6 N 0.1449(3) 0.23022(13) 0.20294(14) 0.0469(6) Uani 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
C1 C2 1.386(2) . ?
C1 C5 1.395(2) . ?
C1 N2 1.4189(19) . ?
F2 C9 1.3357(19) . ?
C2 C3 1.392(2) . ?
C2 H2 0.9500 . ?
F3 C9 1.3366(18) . ?
C3 C4 1.393(2) . ?
C3 C9 1.507(2) . ?
F4 C13 1.3523(17) . ?
C4 N1 1.343(2) . ?
C4 C10 1.451(2) . ?
C5 N1 1.334(2) . ?
C5 H5 0.9500 . ?
C6 N3 1.3487(19) . ?
C6 N2 1.4000(19) . ?
C6 S1 1.6512(16) . ?
C7 N3 1.4654(19) . ?
C7 C8 1.510(2) . ?
C7 C17 1.550(2) . ?
C7 C18 1.560(2) . ?
C8 O1 1.2041(19) . ?
C8 N2 1.3952(19) . ?
C9 F1 1.3400(18) . ?
C10 N4 1.145(2) . ?
C11 C12 1.392(2) . ?
C11 C16 1.394(2) . ?
C11 N3 1.4303(19) . ?
C12 C13 1.380(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(2) . ?
C14 C15 1.401(2) . ?
C14 C20 1.504(2) . ?
C15 C16 1.392(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C19 1.550(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.537(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O2 1.2296(18) . ?
C20 N5 1.338(2) . ?
C21 N5 1.454(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N5 H5N 0.86(3) . ?
C22 C23 1.455(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 N6 1.144(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
C2 C1 C5 119.81(14) . . ?
C2 C1 N2 120.15(14) . . ?
C5 C1 N2 120.00(14) . . ?
C1 C2 C3 117.84(14) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C2 C3 C4 118.43(14) . . ?
C2 C3 C9 120.60(14) . . ?
C4 C3 C9 120.93(14) . . ?
N1 C4 C3 123.85(14) . . ?
N1 C4 C10 115.45(14) . . ?
C3 C4 C10 120.70(14) . . ?
N1 C5 C1 122.67(14) . . ?
N1 C5 H5 118.7 . . ?
C1 C5 H5 118.7 . . ?
N3 C6 N2 106.71(13) . . ?
N3 C6 S1 128.78(12) . . ?
N2 C6 S1 124.49(11) . . ?
N3 C7 C8 101.80(12) . . ?
N3 C7 C17 119.39(13) . . ?
C8 C7 C17 114.26(13) . . ?
N3 C7 C18 121.17(13) . . ?
C8 C7 C18 112.23(12) . . ?
C17 C7 C18 88.53(11) . . ?
O1 C8 N2 125.44(14) . . ?
O1 C8 C7 128.18(14) . . ?
N2 C8 C7 106.33(13) . . ?
F2 C9 F3 107.59(14) . . ?
F2 C9 F1 106.57(13) . . ?
F3 C9 F1 106.62(13) . . ?
F2 C9 C3 111.84(13) . . ?
F3 C9 C3 111.87(13) . . ?
F1 C9 C3 112.02(14) . . ?
N4 C10 C4 178.74(17) . . ?
C12 C11 C16 120.70(14) . . ?
C12 C11 N3 118.52(14) . . ?
C16 C11 N3 120.75(14) . . ?
C13 C12 C11 118.37(14) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
F4 C13 C12 117.56(14) . . ?
F4 C13 C14 119.38(14) . . ?
C12 C13 C14 123.07(15) . . ?
C13 C14 C15 117.28(14) . . ?
C13 C14 C20 123.63(14) . . ?
C15 C14 C20 119.06(13) . . ?
C16 C15 C14 121.21(14) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C11 119.34(14) . . ?
C15 C16 H16 120.3 . . ?
C11 C16 H16 120.3 . . ?
C7 C17 C19 88.59(12) . . ?
C7 C17 H17A 113.9 . . ?
C19 C17 H17A 113.9 . . ?
C7 C17 H17B 113.9 . . ?
C19 C17 H17B 113.9 . . ?
H17A C17 H17B 111.1 . . ?
C19 C18 C7 88.71(12) . . ?
C19 C18 H18A 113.9 . . ?
C7 C18 H18A 113.9 . . ?
C19 C18 H18B 113.9 . . ?
C7 C18 H18B 113.9 . . ?
H18A C18 H18B 111.1 . . ?
C18 C19 C17 89.35(12) . . ?
C18 C19 H19A 113.8 . . ?
C17 C19 H19A 113.8 . . ?
C18 C19 H19B 113.8 . . ?
C17 C19 H19B 113.8 . . ?
H19A C19 H19B 111.0 . . ?
O2 C20 N5 123.05(15) . . ?
O2 C20 C14 120.65(14) . . ?
N5 C20 C14 116.27(14) . . ?
N5 C21 H21A 109.5 . . ?
N5 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N5 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C5 N1 C4 117.29(14) . . ?
C8 N2 C6 111.73(12) . . ?
C8 N2 C1 123.49(13) . . ?
C6 N2 C1 124.43(12) . . ?
C6 N3 C11 123.36(13) . . ?
C6 N3 C7 113.01(13) . . ?
C11 N3 C7 123.58(12) . . ?
C20 N5 C21 121.41(15) . . ?
C20 N5 H5N 119.4(18) . . ?
C21 N5 H5N 119.1(18) . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N6 C23 C22 178.6(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
C5 C1 C2 C3 1.5(2) . . . . ?
N2 C1 C2 C3 179.06(13) . . . . ?
C1 C2 C3 C4 1.6(2) . . . . ?
C1 C2 C3 C9 -175.96(14) . . . . ?
C2 C3 C4 N1 -3.4(2) . . . . ?
C9 C3 C4 N1 174.22(14) . . . . ?
C2 C3 C4 C10 176.84(14) . . . . ?
C9 C3 C4 C10 -5.6(2) . . . . ?
C2 C1 C5 N1 -3.4(2) . . . . ?
N2 C1 C5 N1 179.06(14) . . . . ?
N3 C7 C8 O1 178.95(15) . . . . ?
C17 C7 C8 O1 48.8(2) . . . . ?
C18 C7 C8 O1 -50.0(2) . . . . ?
N3 C7 C8 N2 -3.37(15) . . . . ?
C17 C7 C8 N2 -133.47(13) . . . . ?
C18 C7 C8 N2 127.68(13) . . . . ?
C2 C3 C9 F2 113.00(16) . . . . ?
C4 C3 C9 F2 -64.52(19) . . . . ?
C2 C3 C9 F3 -7.8(2) . . . . ?
C4 C3 C9 F3 174.70(14) . . . . ?
C2 C3 C9 F1 -127.44(15) . . . . ?
C4 C3 C9 F1 55.05(19) . . . . ?
C16 C11 C12 C13 0.7(2) . . . . ?
N3 C11 C12 C13 178.87(13) . . . . ?
C11 C12 C13 F4 -178.55(13) . . . . ?
C11 C12 C13 C14 0.9(2) . . . . ?
F4 C13 C14 C15 177.59(13) . . . . ?
C12 C13 C14 C15 -1.9(2) . . . . ?
F4 C13 C14 C20 -0.3(2) . . . . ?
C12 C13 C14 C20 -179.76(14) . . . . ?
C13 C14 C15 C16 1.2(2) . . . . ?
C20 C14 C15 C16 179.23(14) . . . . ?
C14 C15 C16 C11 0.3(2) . . . . ?
C12 C11 C16 C15 -1.3(2) . . . . ?
N3 C11 C16 C15 -179.40(14) . . . . ?
N3 C7 C17 C19 141.81(14) . . . . ?
C8 C7 C17 C19 -97.43(14) . . . . ?
C18 C7 C17 C19 16.37(13) . . . . ?
N3 C7 C18 C19 -140.45(15) . . . . ?
C8 C7 C18 C19 99.18(15) . . . . ?
C17 C7 C18 C19 -16.51(13) . . . . ?
C7 C18 C19 C17 16.51(13) . . . . ?
C7 C17 C19 C18 -16.61(13) . . . . ?
C13 C14 C20 O2 139.05(16) . . . . ?
C15 C14 C20 O2 -38.8(2) . . . . ?
C13 C14 C20 N5 -42.8(2) . . . . ?
C15 C14 C20 N5 139.31(15) . . . . ?
C1 C5 N1 C4 1.8(2) . . . . ?
C3 C4 N1 C5 1.6(2) . . . . ?
C10 C4 N1 C5 -178.57(14) . . . . ?
O1 C8 N2 C6 -175.99(15) . . . . ?
C7 C8 N2 C6 6.25(16) . . . . ?
O1 C8 N2 C1 -2.6(2) . . . . ?
C7 C8 N2 C1 179.66(13) . . . . ?
N3 C6 N2 C8 -6.63(17) . . . . ?
S1 C6 N2 C8 172.14(11) . . . . ?
N3 C6 N2 C1 -179.96(13) . . . . ?
S1 C6 N2 C1 -1.2(2) . . . . ?
C2 C1 N2 C8 -52.2(2) . . . . ?
C5 C1 N2 C8 125.34(15) . . . . ?
C2 C1 N2 C6 120.38(16) . . . . ?
C5 C1 N2 C6 -62.1(2) . . . . ?
N2 C6 N3 C11 -178.06(13) . . . . ?
S1 C6 N3 C11 3.2(2) . . . . ?
N2 C6 N3 C7 4.25(17) . . . . ?
S1 C6 N3 C7 -174.44(12) . . . . ?
C12 C11 N3 C6 106.67(17) . . . . ?
C16 C11 N3 C6 -75.2(2) . . . . ?
C12 C11 N3 C7 -75.89(19) . . . . ?
C16 C11 N3 C7 102.29(18) . . . . ?
C8 C7 N3 C6 -0.56(16) . . . . ?
C17 C7 N3 C6 126.28(15) . . . . ?
C18 C7 N3 C6 -125.88(15) . . . . ?
C8 C7 N3 C11 -178.24(13) . . . . ?
C17 C7 N3 C11 -51.4(2) . . . . ?
C18 C7 N3 C11 56.4(2) . . . . ?
O2 C20 N5 C21 -0.2(3) . . . . ?
C14 C20 N5 C21 -178.28(15) . . . . ?

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
_geom_hbond_publ_flag
N5 H5N N6 0.86(3) 2.30(3) 3.155(3) 171(2) . yes
C2 H2 O2 0.95 2.39 3.1022(19) 132 2_665 yes
C12 H12 S1 0.95 2.80 3.6131(16) 144 4_455 yes
C15 H15 O1 0.95 2.47 3.4059(19) 168 2_664 yes
C18 H18A N4 0.99 2.54 3.475(2) 158 3_554 yes

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_KB02_0m_a_APA-CHY-1-1
_database_code_depnum_ccdc_archive 'CCDC 2152154'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-02-15 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            Apalutamide-Cyclohexanone-1:1
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 F4 N5 O2 S, C6 H10 O'
_chemical_formula_sum            'C27 H25 F4 N5 O3 S'
_chemical_formula_weight         575.58

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   25.2912(7)
_cell_length_b                   12.4809(4)
_cell_length_c                   17.6369(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.1090(10)
_cell_angle_gamma                90
_cell_volume                     5291.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6955
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      24.23

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             2384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.190
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6298
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46140
_diffrn_reflns_av_unetI/netI     0.1294
_diffrn_reflns_av_R_equivalents  0.1037
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.034
_diffrn_reflns_theta_max         24.725
_diffrn_reflns_theta_full        24.725
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9019
_reflns_number_gt                5179
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+9.1283P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         9019
_refine_ls_number_parameters     815
_refine_ls_number_restraints     210
_refine_ls_R_factor_all          0.1513
_refine_ls_R_factor_gt           0.0767
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.031
_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
C1A C 0.2428(2) 1.1821(4) 0.5813(3) 0.0227(12) Uani 1 1 d . . . . .
C2A C 0.1887(2) 1.1653(4) 0.5365(3) 0.0310(13) Uani 1 1 d . . . . .
H2A H 0.175023 1.094533 0.523662 0.037 Uiso 1 1 calc R U . . .
C3A C 0.15447(19) 1.2519(4) 0.5101(3) 0.0246(12) Uani 1 1 d . . . . .
C4A C 0.1761(2) 1.3529(4) 0.5310(3) 0.0226(12) Uani 1 1 d . . . . .
C5A C 0.2612(2) 1.2862(4) 0.5977(3) 0.0274(12) Uani 1 1 d . . . . .
H5A H 0.298934 1.297294 0.628393 0.033 Uiso 1 1 calc R U . . .
C6A C 0.32010(18) 1.0613(4) 0.5776(3) 0.0203(11) Uani 1 1 d . . . . .
C7A C 0.32091(19) 0.9444(4) 0.6825(3) 0.0236(12) Uani 1 1 d . . . . .
C8A C 0.2737(2) 1.0227(4) 0.6684(3) 0.0245(12) Uani 1 1 d . . . . .
C9A C 0.0960(2) 1.2380(5) 0.4575(3) 0.0442(15) Uani 1 1 d . . . . .
C10A C 0.1423(2) 1.4490(5) 0.5045(3) 0.0259(12) Uani 1 1 d . . . . .
C11A C 0.38074(19) 0.9040(4) 0.5932(3) 0.0195(11) Uani 1 1 d . . . . .
C12A C 0.35778(19) 0.8330(4) 0.5317(3) 0.0228(12) Uani 1 1 d . . . . .
H12A H 0.318654 0.829960 0.506950 0.027 Uiso 1 1 calc R U . . .
C13A C 0.3924(2) 0.7674(4) 0.5072(3) 0.0225(12) Uani 1 1 d . . . . .
H131 H 0.376382 0.719487 0.464282 0.027 Uiso 0.380(7) 1 calc R U P A 2
C14A C 0.44928(19) 0.7667(4) 0.5412(2) 0.0178(11) Uani 1 1 d . . . . .
C15A C 0.4710(2) 0.8374(4) 0.6048(3) 0.0264(12) Uani 1 1 d . . . . .
H15A H 0.510013 0.838065 0.630875 0.032 Uiso 0.620(7) 1 calc R U P A 1
C16A C 0.4375(2) 0.9061(4) 0.6310(3) 0.0247(12) Uani 1 1 d . . . . .
H16A H 0.453205 0.953926 0.674051 0.030 Uiso 1 1 calc R U . . .
C17A C 0.36287(19) 0.9423(4) 0.7683(3) 0.0292(13) Uani 1 1 d . . . . .
H17A H 0.400070 0.970964 0.771960 0.035 Uiso 1 1 calc R U . . .
H17B H 0.348443 0.975348 0.808990 0.035 Uiso 1 1 calc R U . . .
C18A C 0.30941(19) 0.8247(4) 0.6917(3) 0.0246(12) Uani 1 1 d . . . . .
H18A H 0.273685 0.810532 0.701843 0.030 Uiso 1 1 calc R U . . .
H18B H 0.313364 0.779290 0.647733 0.030 Uiso 1 1 calc R U . . .
C19A C 0.3598(3) 0.8220(5) 0.7665(3) 0.0563(18) Uani 1 1 d . . . . .
H19A H 0.351771 0.790739 0.813321 0.068 Uiso 1 1 calc R U . . .
H19B H 0.392799 0.787465 0.758119 0.068 Uiso 1 1 calc R U . . .
C20A C 0.4849(2) 0.6974(4) 0.5077(3) 0.0215(11) Uani 1 1 d . . . . .
C21A C 0.56377(19) 0.5752(4) 0.5340(3) 0.0319(13) Uani 1 1 d . . . . .
H21A H 0.547137 0.555387 0.477846 0.048 Uiso 1 1 calc R U . . .
H21B H 0.571787 0.510213 0.566825 0.048 Uiso 1 1 calc R U . . .
H21C H 0.598391 0.614699 0.540587 0.048 Uiso 1 1 calc R U . . .
S1A S 0.33429(5) 1.12080(10) 0.50298(7) 0.0260(3) Uani 1 1 d . . . . .
F1A F 0.08020(12) 1.1366(3) 0.44919(19) 0.0536(9) Uani 1 1 d . . . . .
F2A F 0.05886(11) 1.2922(2) 0.48161(17) 0.0448(8) Uani 1 1 d . . . . .
F3A F 0.08933(12) 1.2744(3) 0.38166(18) 0.0546(9) Uani 1 1 d . . . . .
F4A F 0.37158(17) 0.6973(4) 0.4507(2) 0.0380(17) Uani 0.620(7) 1 d . . P A 1
F41 F 0.5221(3) 0.8388(5) 0.6378(4) 0.025(2) Uani 0.380(7) 1 d . . P A 2
O1A O 0.23844(14) 1.0263(3) 0.7009(2) 0.0369(9) Uani 1 1 d . . . . .
O2A O 0.47506(14) 0.6915(3) 0.43505(19) 0.0397(10) Uani 1 1 d . . . . .
N1A N 0.22937(16) 1.3715(3) 0.5734(2) 0.0255(10) Uani 1 1 d . . . . .
N2A N 0.27961(15) 1.0947(3) 0.6111(2) 0.0225(9) Uani 1 1 d . . . . .
N3A N 0.34456(15) 0.9734(3) 0.6187(2) 0.0206(9) Uani 1 1 d . . . . .
N4A N 0.11489(18) 1.5215(4) 0.4817(2) 0.0379(12) Uani 1 1 d . . . . .
N5A N 0.52521(17) 0.6422(3) 0.5589(3) 0.0241(11) Uani 1 1 d . . . . .
H5N H 0.5281(17) 0.641(3) 0.604(3) 0.016(14) Uiso 1 1 d . . . . .
C1B C 0.21939(19) 0.2125(4) 0.8198(3) 0.0209(11) Uani 1 1 d . . . . .
C2B C 0.2488(2) 0.1386(4) 0.8749(3) 0.0235(12) Uani 1 1 d . . . . .
H2B H 0.284109 0.155586 0.911749 0.028 Uiso 1 1 calc R U . . .
C3B C 0.2250(2) 0.0381(4) 0.8745(3) 0.0263(12) Uani 1 1 d . . . . .
C4B C 0.1720(2) 0.0199(4) 0.8206(3) 0.0268(12) Uani 1 1 d . . . . .
C5B C 0.16695(19) 0.1878(4) 0.7693(3) 0.0259(12) Uani 1 1 d . . . . .
H5B H 0.147237 0.240826 0.732706 0.031 Uiso 1 1 calc R U . . .
C6B C 0.29425(18) 0.3325(4) 0.8029(2) 0.0187(11) Uani 1 1 d . . . . .
C7B C 0.24820(18) 0.4986(4) 0.7928(3) 0.0192(11) Uani 1 1 d . . . . .
C8B C 0.21408(19) 0.4111(4) 0.8133(2) 0.0205(11) Uani 1 1 d . . . . .
C9B C 0.2572(2) -0.0494(4) 0.9263(3) 0.0382(14) Uani 1 1 d . . . . .
C10B C 0.1443(2) -0.0827(5) 0.8156(3) 0.0388(14) Uani 1 1 d . . . . .
C11B C 0.34673(18) 0.4901(3) 0.7846(3) 0.0175(11) Uani 1 1 d . . . . .
C12B C 0.35075(19) 0.5146(3) 0.7095(3) 0.0207(11) Uani 1 1 d . . . . .
H12B H 0.321316 0.497858 0.662393 0.025 Uiso 1 1 calc R U . . .
C13B C 0.39846(19) 0.5635(4) 0.7053(2) 0.0192(11) Uani 1 1 d . . . . .
H132 H 0.401597 0.579601 0.654237 0.023 Uiso 0.333(6) 1 calc R U P B 2
C14B C 0.44239(18) 0.5906(3) 0.7727(3) 0.0183(11) Uani 1 1 d . . . . .
C15B C 0.43611(19) 0.5648(4) 0.8463(3) 0.0213(11) Uani 1 1 d . . . . .
H15B H 0.465230 0.582396 0.893537 0.026 Uiso 0.667(6) 1 calc R U P B 1
C16B C 0.38935(19) 0.5149(3) 0.8531(3) 0.0178(11) Uani 1 1 d . . . C 1
H16B H 0.386383 0.497817 0.904121 0.021 Uiso 1 1 calc R U . C 1
C17B C 0.25328(18) 0.6001(3) 0.8448(3) 0.0207(11) Uani 1 1 d . . . D 1
H17C H 0.243725 0.588255 0.894537 0.025 Uiso 1 1 calc R U . D 1
H17D H 0.289395 0.637533 0.855889 0.025 Uiso 1 1 calc R U . D 1
C18B C 0.21613(19) 0.5660(4) 0.7194(3) 0.0232(12) Uani 1 1 d . . . D 1
H18C H 0.239461 0.591751 0.687309 0.028 Uiso 1 1 calc R U . D 1
H18D H 0.181755 0.531400 0.685265 0.028 Uiso 1 1 calc R U . D 1
C19B C 0.20595(18) 0.6507(4) 0.7768(3) 0.0227(11) Uani 1 1 d . . . D 1
H19C H 0.168921 0.645341 0.784626 0.027 Uiso 1 1 calc R U . D 1
H19D H 0.213663 0.724995 0.763721 0.027 Uiso 1 1 calc R U . D 1
C20B C 0.49411(19) 0.6429(4) 0.7658(3) 0.0204(11) Uani 1 1 d . . . E 1
C21B C 0.5637(2) 0.7817(4) 0.8194(3) 0.0363(14) Uani 1 1 d . . . F 1
H21D H 0.556496 0.858973 0.816056 0.055 Uiso 1 1 calc R U . F 1
H21E H 0.577263 0.759530 0.775513 0.055 Uiso 1 1 calc R U . F 1
H21F H 0.591752 0.764940 0.870451 0.055 Uiso 1 1 calc R U . F 1
S1B S 0.34123(5) 0.24126(10) 0.80448(7) 0.0247(3) Uani 1 1 d . . . G 1
F1B F 0.30637(12) -0.0157(2) 0.97382(18) 0.0447(8) Uani 1 1 d . . . H 1
F2B F 0.26750(12) -0.1297(2) 0.8815(2) 0.0577(9) Uani 1 1 d . . . I 1
F3B F 0.23084(12) -0.0933(2) 0.9733(2) 0.0595(10) Uani 1 1 d . . . J 1
F4B F 0.40177(15) 0.5845(3) 0.6317(2) 0.0292(14) Uani 0.667(6) 1 d . . P B 1
F42 F 0.4784(3) 0.5747(6) 0.9157(4) 0.025(3) Uani 0.333(6) 1 d . . P B 2
O1B O 0.16992(13) 0.4199(2) 0.82679(18) 0.0278(8) Uani 1 1 d . . . . .
O2B O 0.51700(12) 0.6090(3) 0.71782(18) 0.0277(8) Uani 1 1 d . . . . .
N1B N 0.14275(16) 0.0924(3) 0.7695(2) 0.0289(10) Uani 1 1 d . . . . .
N2B N 0.24212(15) 0.3150(3) 0.8128(2) 0.0195(9) Uani 1 1 d . . . . .
N3B N 0.29754(14) 0.4389(3) 0.7912(2) 0.0184(9) Uani 1 1 d . . . . .
N4B N 0.12156(19) -0.1628(4) 0.8082(3) 0.0534(14) Uani 1 1 d . . . . .
N5B N 0.51271(17) 0.7250(4) 0.8140(3) 0.0253(11) Uani 1 1 d . . . . .
H2N H 0.497(2) 0.747(4) 0.843(3) 0.029(16) Uiso 1 1 d . . . . .
C22A C 0.0637(2) 0.4196(4) 0.6512(3) 0.0294(13) Uani 1 1 d . . . . .
C23A C 0.0477(2) 0.5325(4) 0.6280(3) 0.0360(14) Uani 1 1 d . . . . .
H23A H 0.013560 0.533521 0.581350 0.043 Uiso 1 1 calc R U . . .
H23B H 0.077725 0.568108 0.612450 0.043 Uiso 1 1 calc R U . . .
C24A C 0.0372(2) 0.5942(4) 0.6970(3) 0.0375(14) Uani 1 1 d . . . . .
H24A H 0.072613 0.602709 0.740764 0.045 Uiso 1 1 calc R U . . .
H24B H 0.022728 0.666527 0.678590 0.045 Uiso 1 1 calc R U . . .
C25A C -0.0043(2) 0.5354(5) 0.7278(3) 0.0431(15) Uani 1 1 d . . . . .
H25A H -0.009915 0.575361 0.773216 0.052 Uiso 1 1 calc R U . . .
H25B H -0.040572 0.531137 0.685143 0.052 Uiso 1 1 calc R U . . .
C26A C 0.0163(2) 0.4241(5) 0.7544(3) 0.0458(16) Uani 1 1 d . . . . .
H26A H -0.011283 0.386762 0.774388 0.055 Uiso 1 1 calc R U . . .
H26B H 0.051613 0.428776 0.798723 0.055 Uiso 1 1 calc R U . . .
C27A C 0.0255(2) 0.3600(4) 0.6868(3) 0.0438(15) Uani 1 1 d . . . . .
H27A H 0.042007 0.289677 0.707051 0.053 Uiso 1 1 calc R U . . .
H27B H -0.010569 0.347207 0.645261 0.053 Uiso 1 1 calc R U . . .
O3A O 0.10636(15) 0.3797(3) 0.64507(19) 0.0396(9) Uani 1 1 d . . . . .
O3B O 0.2116(12) 0.902(3) 0.5184(11) 0.036(4) Uani 0.538(6) 1 d . U P K 3
C22B C 0.1732(8) 0.8516(17) 0.5303(7) 0.028(3) Uani 0.538(6) 1 d D U P K 3
C23B C 0.1485(4) 0.8348(9) 0.5968(6) 0.038(3) Uani 0.538(6) 1 d D U P K 3
H23C H 0.170521 0.874660 0.644775 0.046 Uiso 0.538(6) 1 calc R U P K 3
H23D H 0.149815 0.757770 0.610595 0.046 Uiso 0.538(6) 1 calc R U P K 3
C24B C 0.0882(4) 0.8737(10) 0.5717(6) 0.044(3) Uani 0.538(6) 1 d D U P K 3
H24C H 0.087657 0.952726 0.566632 0.052 Uiso 0.538(6) 1 calc R U P K 3
H24D H 0.071427 0.854762 0.613622 0.052 Uiso 0.538(6) 1 calc R U P K 3
C25B C 0.0532(5) 0.8246(12) 0.4922(7) 0.048(3) Uani 0.538(6) 1 d D U P K 3
H25C H 0.050795 0.746013 0.498047 0.058 Uiso 0.538(6) 1 calc R U P K 3
H25D H 0.015075 0.854278 0.476784 0.058 Uiso 0.538(6) 1 calc R U P K 3
C26B C 0.0796(4) 0.8493(9) 0.4279(6) 0.038(3) Uani 0.538(6) 1 d D U P K 3
H26C H 0.079057 0.927749 0.419249 0.046 Uiso 0.538(6) 1 calc R U P K 3
H26D H 0.057410 0.815343 0.377314 0.046 Uiso 0.538(6) 1 calc R U P K 3
C27B C 0.1395(4) 0.8091(9) 0.4501(5) 0.035(3) Uani 0.538(6) 1 d D U P K 3
H27C H 0.139775 0.729807 0.451406 0.042 Uiso 0.538(6) 1 calc R U P K 3
H27D H 0.156372 0.832548 0.409214 0.042 Uiso 0.538(6) 1 calc R U P K 3
O3D O 0.2192(14) 0.893(3) 0.5415(13) 0.034(4) Uani 0.462(6) 1 d . U P K 4
C22D C 0.1680(8) 0.8551(19) 0.5088(10) 0.027(3) Uani 0.462(6) 1 d D U P K 4
C23D C 0.1632(5) 0.7636(10) 0.5616(7) 0.038(3) Uani 0.462(6) 1 d D U P K 4
H23E H 0.199774 0.749413 0.601732 0.046 Uiso 0.462(6) 1 calc R U P K 4
H23F H 0.151180 0.697933 0.529344 0.046 Uiso 0.462(6) 1 calc R U P K 4
C24D C 0.1211(5) 0.7931(11) 0.6027(7) 0.044(3) Uani 0.462(6) 1 d D U P K 4
H24E H 0.134866 0.855778 0.637689 0.052 Uiso 0.462(6) 1 calc R U P K 4
H24F H 0.116989 0.732608 0.636775 0.052 Uiso 0.462(6) 1 calc R U P K 4
C25D C 0.0650(6) 0.8194(13) 0.5436(9) 0.048(4) Uani 0.462(6) 1 d D U P K 4
H25E H 0.050013 0.755774 0.510340 0.057 Uiso 0.462(6) 1 calc R U P K 4
H25F H 0.038607 0.839511 0.572499 0.057 Uiso 0.462(6) 1 calc R U P K 4
C26D C 0.0713(5) 0.9110(11) 0.4912(7) 0.046(3) Uani 0.462(6) 1 d D U P K 4
H26E H 0.082611 0.976082 0.524384 0.055 Uiso 0.462(6) 1 calc R U P K 4
H26F H 0.034789 0.925617 0.451037 0.055 Uiso 0.462(6) 1 calc R U P K 4
C27D C 0.1141(5) 0.8878(11) 0.4484(6) 0.034(3) Uani 0.462(6) 1 d D U P K 4
H27E H 0.100489 0.829618 0.409003 0.041 Uiso 0.462(6) 1 calc R U P K 4
H27F H 0.119938 0.952587 0.419620 0.041 Uiso 0.462(6) 1 calc R U P K 4


_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
C1A C2A 1.368(6) . ?
C1A C5A 1.379(6) . ?
C1A N2A 1.424(6) . ?
C2A C3A 1.373(6) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.378(6) . ?
C3A C9A 1.492(7) . ?
C4A N1A 1.342(6) . ?
C4A C10A 1.462(7) . ?
C5A N1A 1.323(6) . ?
C5A H5A 0.9500 . ?
C6A N3A 1.354(5) . ?
C6A N2A 1.396(5) . ?
C6A S1A 1.645(5) . ?
C7A N3A 1.474(5) . ?
C7A C8A 1.503(6) . ?
C7A C18A 1.540(6) . ?
C7A C17A 1.555(6) . ?
C8A O1A 1.201(5) . ?
C8A N2A 1.394(6) . ?
C9A F1A 1.321(6) . ?
C9A F2A 1.329(6) . ?
C9A F3A 1.373(6) . ?
C10A N4A 1.136(6) . ?
C11A C12A 1.381(6) . ?
C11A C16A 1.383(6) . ?
C11A N3A 1.431(5) . ?
C12A C13A 1.364(6) . ?
C12A H12A 0.9500 . ?
C13A F4A 1.306(6) . ?
C13A C14A 1.376(6) . ?
C13A H131 0.9500 . ?
C14A C15A 1.398(6) . ?
C14A C20A 1.497(6) . ?
C15A F41 1.243(7) . ?
C15A C16A 1.382(6) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C17A C19A 1.503(7) . ?
C17A H17A 0.9900 . ?
C17A H17B 0.9900 . ?
C18A C19A 1.523(7) . ?
C18A H18A 0.9900 . ?
C18A H18B 0.9900 . ?
C19A H19A 0.9900 . ?
C19A H19B 0.9900 . ?
C20A O2A 1.228(5) . ?
C20A N5A 1.326(6) . ?
C21A N5A 1.453(6) . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
N5A H5N 0.77(4) . ?
C1B C2B 1.379(6) . ?
C1B C5B 1.384(6) . ?
C1B N2B 1.424(5) . ?
C2B C3B 1.391(6) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.398(7) . ?
C3B C9B 1.493(7) . ?
C4B N1B 1.329(6) . ?
C4B C10B 1.449(7) . ?
C5B N1B 1.339(6) . ?
C5B H5B 0.9500 . ?
C6B N3B 1.350(5) . ?
C6B N2B 1.400(5) . ?
C6B S1B 1.639(5) . ?
C7B N3B 1.461(5) . ?
C7B C8B 1.503(6) . ?
C7B C18B 1.546(6) . ?
C7B C17B 1.546(6) . ?
C8B O1B 1.217(5) . ?
C8B N2B 1.395(6) . ?
C9B F3B 1.331(6) . ?
C9B F1B 1.334(6) . ?
C9B F2B 1.351(6) . ?
C10B N4B 1.141(6) . ?
C11B C16B 1.381(6) . ?
C11B C12B 1.395(6) . ?
C11B N3B 1.435(5) . ?
C12B C13B 1.375(6) . ?
C12B H12B 0.9500 . ?
C13B F4B 1.353(5) . ?
C13B C14B 1.393(6) . ?
C13B H132 0.9500 . ?
C14B C15B 1.395(6) . ?
C14B C20B 1.500(6) . ?
C15B F42 1.357(8) . ?
C15B C16B 1.375(6) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
C17B C19B 1.542(6) . ?
C17B H17C 0.9900 . ?
C17B H17D 0.9900 . ?
C18B C19B 1.540(6) . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C20B O2B 1.239(5) . ?
C20B N5B 1.321(6) . ?
C21B N5B 1.447(6) . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
N5B H2N 0.78(5) . ?
C22A O3A 1.222(5) . ?
C22A C23A 1.489(7) . ?
C22A C27A 1.502(7) . ?
C23A C24A 1.532(7) . ?
C23A H23A 0.9900 . ?
C23A H23B 0.9900 . ?
C24A C25A 1.513(7) . ?
C24A H24A 0.9900 . ?
C24A H24B 0.9900 . ?
C25A C26A 1.507(7) . ?
C25A H25A 0.9900 . ?
C25A H25B 0.9900 . ?
C26A C27A 1.512(7) . ?
C26A H26A 0.9900 . ?
C26A H26B 0.9900 . ?
C27A H27A 0.9900 . ?
C27A H27B 0.9900 . ?
O3B C22B 1.23(4) . ?
C22B C27B 1.503(15) . ?
C22B C23B 1.507(16) . ?
C23B C24B 1.527(12) . ?
C23B H23C 0.9900 . ?
C23B H23D 0.9900 . ?
C24B C25B 1.534(13) . ?
C24B H24C 0.9900 . ?
C24B H24D 0.9900 . ?
C25B C26B 1.514(13) . ?
C25B H25C 0.9900 . ?
C25B H25D 0.9900 . ?
C26B C27B 1.527(12) . ?
C26B H26C 0.9900 . ?
C26B H26D 0.9900 . ?
C27B H27C 0.9900 . ?
C27B H27D 0.9900 . ?
O3D C22D 1.33(4) . ?
C22D C27D 1.501(17) . ?
C22D C23D 1.502(17) . ?
C23D C24D 1.507(13) . ?
C23D H23E 0.9900 . ?
C23D H23F 0.9900 . ?
C24D C25D 1.514(14) . ?
C24D H24E 0.9900 . ?
C24D H24F 0.9900 . ?
C25D C26D 1.508(14) . ?
C25D H25E 0.9900 . ?
C25D H25F 0.9900 . ?
C26D C27D 1.529(13) . ?
C26D H26E 0.9900 . ?
C26D H26F 0.9900 . ?
C27D H27E 0.9900 . ?
C27D H27F 0.9900 . ?

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
C2A C1A C5A 118.5(5) . . ?
C2A C1A N2A 121.1(4) . . ?
C5A C1A N2A 120.4(4) . . ?
C1A C2A C3A 119.2(5) . . ?
C1A C2A H2A 120.4 . . ?
C3A C2A H2A 120.4 . . ?
C2A C3A C4A 118.3(4) . . ?
C2A C3A C9A 121.2(5) . . ?
C4A C3A C9A 120.5(5) . . ?
N1A C4A C3A 123.6(4) . . ?
N1A C4A C10A 115.0(4) . . ?
C3A C4A C10A 121.4(4) . . ?
N1A C5A C1A 124.0(5) . . ?
N1A C5A H5A 118.0 . . ?
C1A C5A H5A 118.0 . . ?
N3A C6A N2A 106.7(4) . . ?
N3A C6A S1A 128.2(3) . . ?
N2A C6A S1A 125.1(4) . . ?
N3A C7A C8A 101.8(4) . . ?
N3A C7A C18A 116.9(4) . . ?
C8A C7A C18A 118.8(4) . . ?
N3A C7A C17A 115.5(4) . . ?
C8A C7A C17A 116.0(4) . . ?
C18A C7A C17A 88.6(3) . . ?
O1A C8A N2A 125.8(5) . . ?
O1A C8A C7A 127.9(4) . . ?
N2A C8A C7A 106.3(4) . . ?
F1A C9A F2A 107.8(5) . . ?
F1A C9A F3A 105.5(4) . . ?
F2A C9A F3A 104.9(4) . . ?
F1A C9A C3A 112.8(5) . . ?
F2A C9A C3A 113.8(4) . . ?
F3A C9A C3A 111.3(5) . . ?
N4A C10A C4A 177.6(5) . . ?
C12A C11A C16A 120.8(4) . . ?
C12A C11A N3A 118.8(4) . . ?
C16A C11A N3A 120.4(4) . . ?
C13A C12A C11A 118.7(4) . . ?
C13A C12A H12A 120.7 . . ?
C11A C12A H12A 120.7 . . ?
F4A C13A C12A 119.8(5) . . ?
F4A C13A C14A 116.6(4) . . ?
C12A C13A C14A 123.5(4) . . ?
C12A C13A H131 118.2 . . ?
C14A C13A H131 118.2 . . ?
C13A C14A C15A 116.3(4) . . ?
C13A C14A C20A 120.5(4) . . ?
C15A C14A C20A 123.1(4) . . ?
F41 C15A C16A 119.4(5) . . ?
F41 C15A C14A 118.5(5) . . ?
C16A C15A C14A 122.1(5) . . ?
C16A C15A H15A 119.0 . . ?
C14A C15A H15A 119.0 . . ?
C15A C16A C11A 118.6(4) . . ?
C15A C16A H16A 120.7 . . ?
C11A C16A H16A 120.7 . . ?
C19A C17A C7A 88.9(4) . . ?
C19A C17A H17A 113.8 . . ?
C7A C17A H17A 113.8 . . ?
C19A C17A H17B 113.8 . . ?
C7A C17A H17B 113.8 . . ?
H17A C17A H17B 111.1 . . ?
C19A C18A C7A 88.7(4) . . ?
C19A C18A H18A 113.9 . . ?
C7A C18A H18A 113.9 . . ?
C19A C18A H18B 113.9 . . ?
C7A C18A H18B 113.9 . . ?
H18A C18A H18B 111.1 . . ?
C17A C19A C18A 91.2(4) . . ?
C17A C19A H19A 113.4 . . ?
C18A C19A H19A 113.4 . . ?
C17A C19A H19B 113.4 . . ?
C18A C19A H19B 113.4 . . ?
H19A C19A H19B 110.7 . . ?
O2A C20A N5A 122.9(4) . . ?
O2A C20A C14A 119.6(4) . . ?
N5A C20A C14A 117.4(4) . . ?
N5A C21A H21A 109.5 . . ?
N5A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
N5A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C5A N1A C4A 116.5(4) . . ?
C8A N2A C6A 111.9(4) . . ?
C8A N2A C1A 123.8(4) . . ?
C6A N2A C1A 123.6(4) . . ?
C6A N3A C11A 123.5(4) . . ?
C6A N3A C7A 112.4(4) . . ?
C11A N3A C7A 122.9(4) . . ?
C20A N5A C21A 122.6(4) . . ?
C20A N5A H5N 121(3) . . ?
C21A N5A H5N 116(3) . . ?
C2B C1B C5B 120.3(4) . . ?
C2B C1B N2B 121.3(4) . . ?
C5B C1B N2B 118.4(4) . . ?
C1B C2B C3B 117.5(4) . . ?
C1B C2B H2B 121.3 . . ?
C3B C2B H2B 121.3 . . ?
C2B C3B C4B 118.2(5) . . ?
C2B C3B C9B 120.2(5) . . ?
C4B C3B C9B 121.4(5) . . ?
N1B C4B C3B 124.3(4) . . ?
N1B C4B C10B 113.8(5) . . ?
C3B C4B C10B 121.9(5) . . ?
N1B C5B C1B 122.9(5) . . ?
N1B C5B H5B 118.5 . . ?
C1B C5B H5B 118.5 . . ?
N3B C6B N2B 106.1(4) . . ?
N3B C6B S1B 127.4(3) . . ?
N2B C6B S1B 126.6(3) . . ?
N3B C7B C8B 101.1(4) . . ?
N3B C7B C18B 119.4(4) . . ?
C8B C7B C18B 113.9(4) . . ?
N3B C7B C17B 121.0(4) . . ?
C8B C7B C17B 113.6(4) . . ?
C18B C7B C17B 88.6(3) . . ?
O1B C8B N2B 125.3(4) . . ?
O1B C8B C7B 127.7(4) . . ?
N2B C8B C7B 107.0(4) . . ?
F3B C9B F1B 106.8(5) . . ?
F3B C9B F2B 106.5(4) . . ?
F1B C9B F2B 106.8(4) . . ?
F3B C9B C3B 113.5(4) . . ?
F1B C9B C3B 112.3(4) . . ?
F2B C9B C3B 110.6(5) . . ?
N4B C10B C4B 177.1(7) . . ?
C16B C11B C12B 121.0(4) . . ?
C16B C11B N3B 119.3(4) . . ?
C12B C11B N3B 119.7(4) . . ?
C13B C12B C11B 118.2(4) . . ?
C13B C12B H12B 120.9 . . ?
C11B C12B H12B 120.9 . . ?
F4B C13B C12B 117.0(4) . . ?
F4B C13B C14B 120.0(4) . . ?
C12B C13B C14B 122.9(4) . . ?
C12B C13B H132 118.5 . . ?
C14B C13B H132 118.5 . . ?
C13B C14B C15B 116.5(4) . . ?
C13B C14B C20B 121.4(4) . . ?
C15B C14B C20B 122.0(4) . . ?
F42 C15B C14B 122.2(5) . . ?
C16B C15B C14B 122.4(4) . . ?
C16B C15B H15B 118.8 . . ?
C14B C15B H15B 118.8 . . ?
C15B C16B C11B 119.0(4) . . ?
C15B C16B H16B 120.5 . . ?
C11B C16B H16B 120.5 . . ?
C19B C17B C7B 88.4(3) . . ?
C19B C17B H17C 113.9 . . ?
C7B C17B H17C 113.9 . . ?
C19B C17B H17D 113.9 . . ?
C7B C17B H17D 113.9 . . ?
H17C C17B H17D 111.1 . . ?
C19B C18B C7B 88.6(3) . . ?
C19B C18B H18C 113.9 . . ?
C7B C18B H18C 113.9 . . ?
C19B C18B H18D 113.9 . . ?
C7B C18B H18D 113.9 . . ?
H18C C18B H18D 111.1 . . ?
C18B C19B C17B 89.0(3) . . ?
C18B C19B H19C 113.8 . . ?
C17B C19B H19C 113.8 . . ?
C18B C19B H19D 113.8 . . ?
C17B C19B H19D 113.8 . . ?
H19C C19B H19D 111.0 . . ?
O2B C20B N5B 123.7(4) . . ?
O2B C20B C14B 120.7(4) . . ?
N5B C20B C14B 115.5(4) . . ?
N5B C21B H21D 109.5 . . ?
N5B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
N5B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C4B N1B C5B 116.7(4) . . ?
C8B N2B C6B 111.6(4) . . ?
C8B N2B C1B 123.5(3) . . ?
C6B N2B C1B 124.9(4) . . ?
C6B N3B C11B 123.1(4) . . ?
C6B N3B C7B 113.9(4) . . ?
C11B N3B C7B 122.8(4) . . ?
C20B N5B C21B 123.7(4) . . ?
C20B N5B H2N 123(4) . . ?
C21B N5B H2N 113(4) . . ?
O3A C22A C23A 122.3(5) . . ?
O3A C22A C27A 122.4(5) . . ?
C23A C22A C27A 115.3(5) . . ?
C22A C23A C24A 110.9(4) . . ?
C22A C23A H23A 109.5 . . ?
C24A C23A H23A 109.5 . . ?
C22A C23A H23B 109.5 . . ?
C24A C23A H23B 109.5 . . ?
H23A C23A H23B 108.0 . . ?
C25A C24A C23A 110.6(4) . . ?
C25A C24A H24A 109.5 . . ?
C23A C24A H24A 109.5 . . ?
C25A C24A H24B 109.5 . . ?
C23A C24A H24B 109.5 . . ?
H24A C24A H24B 108.1 . . ?
C26A C25A C24A 110.3(4) . . ?
C26A C25A H25A 109.6 . . ?
C24A C25A H25A 109.6 . . ?
C26A C25A H25B 109.6 . . ?
C24A C25A H25B 109.6 . . ?
H25A C25A H25B 108.1 . . ?
C25A C26A C27A 111.5(4) . . ?
C25A C26A H26A 109.3 . . ?
C27A C26A H26A 109.3 . . ?
C25A C26A H26B 109.3 . . ?
C27A C26A H26B 109.3 . . ?
H26A C26A H26B 108.0 . . ?
C22A C27A C26A 110.2(4) . . ?
C22A C27A H27A 109.6 . . ?
C26A C27A H27A 109.6 . . ?
C22A C27A H27B 109.6 . . ?
C26A C27A H27B 109.6 . . ?
H27A C27A H27B 108.1 . . ?
O3B C22B C27B 105.5(16) . . ?
O3B C22B C23B 138.3(19) . . ?
C27B C22B C23B 115.5(13) . . ?
C22B C23B C24B 110.4(10) . . ?
C22B C23B H23C 109.6 . . ?
C24B C23B H23C 109.6 . . ?
C22B C23B H23D 109.6 . . ?
C24B C23B H23D 109.6 . . ?
H23C C23B H23D 108.1 . . ?
C23B C24B C25B 112.3(9) . . ?
C23B C24B H24C 109.2 . . ?
C25B C24B H24C 109.2 . . ?
C23B C24B H24D 109.2 . . ?
C25B C24B H24D 109.2 . . ?
H24C C24B H24D 107.9 . . ?
C26B C25B C24B 109.8(9) . . ?
C26B C25B H25C 109.7 . . ?
C24B C25B H25C 109.7 . . ?
C26B C25B H25D 109.7 . . ?
C24B C25B H25D 109.7 . . ?
H25C C25B H25D 108.2 . . ?
C25B C26B C27B 111.9(8) . . ?
C25B C26B H26C 109.2 . . ?
C27B C26B H26C 109.2 . . ?
C25B C26B H26D 109.2 . . ?
C27B C26B H26D 109.2 . . ?
H26C C26B H26D 107.9 . . ?
C22B C27B C26B 110.7(11) . . ?
C22B C27B H27C 109.5 . . ?
C26B C27B H27C 109.5 . . ?
C22B C27B H27D 109.5 . . ?
C26B C27B H27D 109.5 . . ?
H27C C27B H27D 108.1 . . ?
O3D C22D C27D 139(2) . . ?
O3D C22D C23D 104.8(17) . . ?
C27D C22D C23D 114.7(15) . . ?
C22D C23D C24D 108.5(14) . . ?
C22D C23D H23E 110.0 . . ?
C24D C23D H23E 110.0 . . ?
C22D C23D H23F 110.0 . . ?
C24D C23D H23F 110.0 . . ?
H23E C23D H23F 108.4 . . ?
C23D C24D C25D 111.9(10) . . ?
C23D C24D H24E 109.2 . . ?
C25D C24D H24E 109.2 . . ?
C23D C24D H24F 109.2 . . ?
C25D C24D H24F 109.2 . . ?
H24E C24D H24F 107.9 . . ?
C26D C25D C24D 109.4(11) . . ?
C26D C25D H25E 109.8 . . ?
C24D C25D H25E 109.8 . . ?
C26D C25D H25F 109.8 . . ?
C24D C25D H25F 109.8 . . ?
H25E C25D H25F 108.2 . . ?
C25D C26D C27D 112.6(11) . . ?
C25D C26D H26E 109.1 . . ?
C27D C26D H26E 109.1 . . ?
C25D C26D H26F 109.1 . . ?
C27D C26D H26F 109.1 . . ?
H26E C26D H26F 107.8 . . ?
C22D C27D C26D 109.1(12) . . ?
C22D C27D H27E 109.9 . . ?
C26D C27D H27E 109.9 . . ?
C22D C27D H27F 109.9 . . ?
C26D C27D H27F 109.9 . . ?
H27E C27D H27F 108.3 . . ?

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
C5A C1A C2A C3A -0.7(7) . . . . ?
N2A C1A C2A C3A 178.9(4) . . . . ?
C1A C2A C3A C4A -0.8(7) . . . . ?
C1A C2A C3A C9A 176.9(5) . . . . ?
C2A C3A C4A N1A 2.4(7) . . . . ?
C9A C3A C4A N1A -175.2(4) . . . . ?
C2A C3A C4A C10A 179.3(4) . . . . ?
C9A C3A C4A C10A 1.7(7) . . . . ?
C2A C1A C5A N1A 0.8(7) . . . . ?
N2A C1A C5A N1A -178.8(4) . . . . ?
N3A C7A C8A O1A 173.3(5) . . . . ?
C18A C7A C8A O1A 43.3(7) . . . . ?
C17A C7A C8A O1A -60.4(7) . . . . ?
N3A C7A C8A N2A -8.7(4) . . . . ?
C18A C7A C8A N2A -138.7(4) . . . . ?
C17A C7A C8A N2A 117.5(4) . . . . ?
C2A C3A C9A F1A 8.2(7) . . . . ?
C4A C3A C9A F1A -174.2(4) . . . . ?
C2A C3A C9A F2A 131.4(5) . . . . ?
C4A C3A C9A F2A -51.0(7) . . . . ?
C2A C3A C9A F3A -110.2(5) . . . . ?
C4A C3A C9A F3A 67.3(6) . . . . ?
C16A C11A C12A C13A -2.1(7) . . . . ?
N3A C11A C12A C13A 179.7(4) . . . . ?
C11A C12A C13A F4A 178.0(4) . . . . ?
C11A C12A C13A C14A 0.9(7) . . . . ?
F4A C13A C14A C15A -176.2(4) . . . . ?
C12A C13A C14A C15A 0.9(7) . . . . ?
F4A C13A C14A C20A 6.8(6) . . . . ?
C12A C13A C14A C20A -176.1(4) . . . . ?
C13A C14A C15A F41 179.3(5) . . . . ?
C20A C14A C15A F41 -3.8(7) . . . . ?
C13A C14A C15A C16A -1.6(6) . . . . ?
C20A C14A C15A C16A 175.2(4) . . . . ?
F41 C15A C16A C11A 179.6(5) . . . . ?
C14A C15A C16A C11A 0.6(7) . . . . ?
C12A C11A C16A C15A 1.4(7) . . . . ?
N3A C11A C16A C15A 179.6(4) . . . . ?
N3A C7A C17A C19A -107.2(5) . . . . ?
C8A C7A C17A C19A 133.8(5) . . . . ?
C18A C7A C17A C19A 12.1(4) . . . . ?
N3A C7A C18A C19A 106.1(5) . . . . ?
C8A C7A C18A C19A -131.1(4) . . . . ?
C17A C7A C18A C19A -12.0(4) . . . . ?
C7A C17A C19A C18A -12.3(4) . . . . ?
C7A C18A C19A C17A 12.4(4) . . . . ?
C13A C14A C20A O2A 42.7(6) . . . . ?
C15A C14A C20A O2A -134.0(5) . . . . ?
C13A C14A C20A N5A -135.4(4) . . . . ?
C15A C14A C20A N5A 47.8(6) . . . . ?
C1A C5A N1A C4A 0.7(6) . . . . ?
C3A C4A N1A C5A -2.3(6) . . . . ?
C10A C4A N1A C5A -179.5(4) . . . . ?
O1A C8A N2A C6A -172.4(4) . . . . ?
C7A C8A N2A C6A 9.6(5) . . . . ?
O1A C8A N2A C1A -1.8(7) . . . . ?
C7A C8A N2A C1A -179.8(4) . . . . ?
N3A C6A N2A C8A -6.1(5) . . . . ?
S1A C6A N2A C8A 174.4(3) . . . . ?
N3A C6A N2A C1A -176.7(4) . . . . ?
S1A C6A N2A C1A 3.9(6) . . . . ?
C2A C1A N2A C8A -66.8(6) . . . . ?
C5A C1A N2A C8A 112.8(5) . . . . ?
C2A C1A N2A C6A 102.7(5) . . . . ?
C5A C1A N2A C6A -77.7(6) . . . . ?
N2A C6A N3A C11A 167.8(4) . . . . ?
S1A C6A N3A C11A -12.8(6) . . . . ?
N2A C6A N3A C7A -0.1(5) . . . . ?
S1A C6A N3A C7A 179.3(3) . . . . ?
C12A C11A N3A C6A -75.9(6) . . . . ?
C16A C11A N3A C6A 105.8(5) . . . . ?
C12A C11A N3A C7A 90.7(5) . . . . ?
C16A C11A N3A C7A -87.5(5) . . . . ?
C8A C7A N3A C6A 5.5(5) . . . . ?
C18A C7A N3A C6A 136.7(4) . . . . ?
C17A C7A N3A C6A -121.1(4) . . . . ?
C8A C7A N3A C11A -162.5(4) . . . . ?
C18A C7A N3A C11A -31.3(6) . . . . ?
C17A C7A N3A C11A 71.0(5) . . . . ?
O2A C20A N5A C21A 4.2(7) . . . . ?
C14A C20A N5A C21A -177.8(4) . . . . ?
C5B C1B C2B C3B 3.0(6) . . . . ?
N2B C1B C2B C3B -176.1(4) . . . . ?
C1B C2B C3B C4B -2.3(6) . . . . ?
C1B C2B C3B C9B 173.3(4) . . . . ?
C2B C3B C4B N1B -0.1(7) . . . . ?
C9B C3B C4B N1B -175.7(4) . . . . ?
C2B C3B C4B C10B 179.3(4) . . . . ?
C9B C3B C4B C10B 3.8(7) . . . . ?
C2B C1B C5B N1B -1.4(7) . . . . ?
N2B C1B C5B N1B 177.8(4) . . . . ?
N3B C7B C8B O1B 175.0(4) . . . . ?
C18B C7B C8B O1B -55.7(6) . . . . ?
C17B C7B C8B O1B 43.8(6) . . . . ?
N3B C7B C8B N2B -6.0(4) . . . . ?
C18B C7B C8B N2B 123.3(4) . . . . ?
C17B C7B C8B N2B -137.2(4) . . . . ?
C2B C3B C9B F3B 126.2(5) . . . . ?
C4B C3B C9B F3B -58.3(6) . . . . ?
C2B C3B C9B F1B 5.0(7) . . . . ?
C4B C3B C9B F1B -179.6(4) . . . . ?
C2B C3B C9B F2B -114.2(5) . . . . ?
C4B C3B C9B F2B 61.3(6) . . . . ?
C16B C11B C12B C13B 0.4(6) . . . . ?
N3B C11B C12B C13B -179.9(4) . . . . ?
C11B C12B C13B F4B 178.7(4) . . . . ?
C11B C12B C13B C14B -0.7(7) . . . . ?
F4B C13B C14B C15B -179.0(4) . . . . ?
C12B C13B C14B C15B 0.5(6) . . . . ?
F4B C13B C14B C20B -0.2(7) . . . . ?
C12B C13B C14B C20B 179.3(4) . . . . ?
C13B C14B C15B F42 171.6(5) . . . . ?
C13B C14B C15B C16B 0.2(6) . . . . ?
C20B C14B C15B C16B -178.6(4) . . . . ?
C14B C15B C16B C11B -0.5(7) . . . . ?
C12B C11B C16B C15B 0.2(6) . . . . ?
N3B C11B C16B C15B -179.4(4) . . . . ?
N3B C7B C17B C19B 141.3(4) . . . . ?
C8B C7B C17B C19B -98.2(4) . . . . ?
C18B C7B C17B C19B 17.4(3) . . . . ?
N3B C7B C18B C19B -142.8(4) . . . . ?
C8B C7B C18B C19B 97.9(4) . . . . ?
C17B C7B C18B C19B -17.5(3) . . . . ?
C7B C18B C19B C17B 17.5(3) . . . . ?
C7B C17B C19B C18B -17.5(3) . . . . ?
C13B C14B C20B O2B -45.5(6) . . . . ?
C15B C14B C20B O2B 133.2(5) . . . . ?
C13B C14B C20B N5B 134.8(4) . . . . ?
C15B C14B C20B N5B -46.4(6) . . . . ?
C3B C4B N1B C5B 1.8(7) . . . . ?
C10B C4B N1B C5B -177.7(4) . . . . ?
C1B C5B N1B C4B -1.0(6) . . . . ?
O1B C8B N2B C6B -174.2(4) . . . . ?
C7B C8B N2B C6B 6.7(5) . . . . ?
O1B C8B N2B C1B 7.0(7) . . . . ?
C7B C8B N2B C1B -172.1(4) . . . . ?
N3B C6B N2B C8B -4.4(5) . . . . ?
S1B C6B N2B C8B 176.0(3) . . . . ?
N3B C6B N2B C1B 174.4(4) . . . . ?
S1B C6B N2B C1B -5.2(6) . . . . ?
C2B C1B N2B C8B -129.1(4) . . . . ?
C5B C1B N2B C8B 51.7(6) . . . . ?
C2B C1B N2B C6B 52.3(6) . . . . ?
C5B C1B N2B C6B -126.9(4) . . . . ?
N2B C6B N3B C11B 175.1(3) . . . . ?
S1B C6B N3B C11B -5.3(6) . . . . ?
N2B C6B N3B C7B 0.1(5) . . . . ?
S1B C6B N3B C7B 179.7(3) . . . . ?
C16B C11B N3B C6B -81.2(5) . . . . ?
C12B C11B N3B C6B 99.1(5) . . . . ?
C16B C11B N3B C7B 93.3(5) . . . . ?
C12B C11B N3B C7B -86.4(5) . . . . ?
C8B C7B N3B C6B 3.6(5) . . . . ?
C18B C7B N3B C6B -122.1(4) . . . . ?
C17B C7B N3B C6B 130.1(4) . . . . ?
C8B C7B N3B C11B -171.3(4) . . . . ?
C18B C7B N3B C11B 62.9(5) . . . . ?
C17B C7B N3B C11B -44.9(6) . . . . ?
O2B C20B N5B C21B -3.3(7) . . . . ?
C14B C20B N5B C21B 176.3(4) . . . . ?
O3A C22A C23A C24A -125.6(5) . . . . ?
C27A C22A C23A C24A 51.2(6) . . . . ?
C22A C23A C24A C25A -53.2(6) . . . . ?
C23A C24A C25A C26A 57.8(6) . . . . ?
C24A C25A C26A C27A -59.1(6) . . . . ?
O3A C22A C27A C26A 125.2(5) . . . . ?
C23A C22A C27A C26A -51.6(6) . . . . ?
C25A C26A C27A C22A 54.5(6) . . . . ?
O3B C22B C23B C24B 119(3) . . . . ?
C27B C22B C23B C24B -50.8(19) . . . . ?
C22B C23B C24B C25B 52.6(15) . . . . ?
C23B C24B C25B C26B -56.8(14) . . . . ?
C24B C25B C26B C27B 57.1(13) . . . . ?
O3B C22B C27B C26B -121(2) . . . . ?
C23B C22B C27B C26B 51.4(18) . . . . ?
C25B C26B C27B C22B -54.0(14) . . . . ?
O3D C22D C23D C24D 113(3) . . . . ?
C27D C22D C23D C24D -56(2) . . . . ?
C22D C23D C24D C25D 57.6(16) . . . . ?
C23D C24D C25D C26D -58.5(17) . . . . ?
C24D C25D C26D C27D 56.1(17) . . . . ?
O3D C22D C27D C26D -111(4) . . . . ?
C23D C22D C27D C26D 54(2) . . . . ?
C25D C26D C27D C22D -53.3(18) . . . . ?

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
_geom_hbond_publ_flag
N5A H5N O2B 0.77(4) 2.15(4) 2.904(5) 165(4) . yes
N5B H2N O2A 0.78(5) 2.03(5) 2.796(6) 167(5) 4_576 yes
C2A H2A O3B 0.95 2.59 3.37(3) 140 . yes
C19A H19A F4A 0.99 2.32 3.179(7) 144 4_576 yes
C5B H5B O3A 0.95 2.34 3.285(6) 175 . yes
C17B H17C O3B 0.99 2.56 3.54(2) 168 4_576 yes
C21B H21E S1B 0.98 2.85 3.753(5) 154 2_656 yes
C23B H23C O1A 0.99 2.54 3.415(12) 147 . yes

_refine_diff_density_max         0.649
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2151551'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C21 H15 F4 N5 O2 S), C3 H6 O'
_chemical_formula_sum            'C45 H36 F8 N10 O5 S2'
_chemical_formula_weight         1012.96

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   43.7534(14)
_cell_length_b                   12.7915(5)
_cell_length_c                   17.9103(6)
_cell_angle_alpha                90
_cell_angle_beta                 113.4810(10)
_cell_angle_gamma                90
_cell_volume                     9193.8(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8633
_cell_measurement_theta_min      2.203
_cell_measurement_theta_max      26.349

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             4160
_exptl_transmission_factor_min   0.7187
_exptl_transmission_factor_max   0.8620
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43641
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.030
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_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             8143
_reflns_number_gt                5609
_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       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0353P)²+30.8120P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00051(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8143
_refine_ls_number_parameters     776
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.1388
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.046
_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 0.34636(3) 0.15707(8) 0.50808(6) 0.0488(3) Uani 1 1 d . . . . .
F1 F 0.32453(6) 0.5732(2) 0.55792(15) 0.0783(9) Uani 1 1 d . . . . .
F11 F 0.48873(6) 0.1207(2) 0.63151(16) 0.0736(8) Uani 1 1 d . . . . .
F12 F 0.50759(6) -0.0085(3) 0.58626(15) 0.0781(9) Uani 1 1 d . . . . .
F13 F 0.48144(5) -0.0384(2) 0.66173(12) 0.0554(6) Uani 1 1 d . . . . .
O11 O 0.25871(8) 0.5595(2) 0.55990(18) 0.0650(9) Uani 1 1 d . . . . .
O12 O 0.39742(7) 0.2383(2) 0.31155(17) 0.0548(8) Uani 1 1 d . . . . .
N11 N 0.23391(7) 0.6229(2) 0.4323(2) 0.0370(7) Uani 1 1 d . . . . .
H1 H 0.2340(10) 0.629(3) 0.385(3) 0.051(13) Uiso 1 1 d . . . . .
N12 N 0.34063(7) 0.3029(2) 0.39553(17) 0.0367(7) Uani 1 1 d . . . . .
N13 N 0.37737(7) 0.1806(2) 0.40543(16) 0.0336(7) Uani 1 1 d . . . . .
N14 N 0.41197(11) -0.0808(3) 0.4158(2) 0.0892(16) Uani 1 1 d . . . . .
N15 N 0.47779(14) -0.2363(4) 0.5131(3) 0.123(2) Uani 1 1 d . . . . .
C11 C 0.31862(9) 0.3682(3) 0.4168(2) 0.0375(9) Uani 1 1 d . . . . .
C12 C 0.33237(9) 0.4396(3) 0.4784(2) 0.0429(9) Uani 1 1 d . . . . .
H12A H 0.355852 0.446458 0.505914 0.052 Uiso 1 1 calc R U . . .
C13 C 0.31117(10) 0.5006(3) 0.4991(2) 0.0436(9) Uani 1 1 d . . . . .
C14 C 0.27715(9) 0.4951(3) 0.4603(2) 0.0367(8) Uani 1 1 d . . . . .
C15 C 0.26390(10) 0.4238(3) 0.3973(3) 0.0464(10) Uani 1 1 d . . . . .
H15A H 0.240414 0.418540 0.368987 0.056 Uiso 1 1 calc R U . . .
C16 C 0.28462(9) 0.3599(3) 0.3751(2) 0.0448(10) Uani 1 1 d . . . . .
H16A H 0.275442 0.311302 0.331749 0.054 Uiso 1 1 calc R U . . .
C17 C 0.25552(10) 0.5622(3) 0.4882(2) 0.0408(9) Uani 1 1 d . . . . .
C18 C 0.21121(9) 0.6912(3) 0.4516(3) 0.0486(10) Uani 1 1 d . . . . .
H18A H 0.210446 0.760015 0.426924 0.073 Uiso 1 1 calc R U . . .
H18B H 0.219144 0.698708 0.510802 0.073 Uiso 1 1 calc R U . . .
H18C H 0.188837 0.660459 0.430054 0.073 Uiso 1 1 calc R U . . .
C21 C 0.35454(9) 0.2161(3) 0.4361(2) 0.0359(8) Uani 1 1 d . . . . .
C22 C 0.35350(9) 0.3330(3) 0.3347(2) 0.0359(8) Uani 1 1 d . . . . .
C23 C 0.37913(9) 0.2490(3) 0.3466(2) 0.0375(9) Uani 1 1 d . . . . .
C24 C 0.36604(10) 0.4447(3) 0.3327(2) 0.0456(10) Uani 1 1 d . . . . .
H24A H 0.356016 0.497649 0.356406 0.055 Uiso 1 1 calc R U . . .
H24B H 0.390625 0.450901 0.355756 0.055 Uiso 1 1 calc R U . . .
C25 C 0.35008(11) 0.4403(4) 0.2394(2) 0.0552(11) Uani 1 1 d . . . . .
H25A H 0.365996 0.423654 0.214391 0.066 Uiso 1 1 calc R U . . .
H25B H 0.336665 0.502892 0.213824 0.066 Uiso 1 1 calc R U . . .
C26 C 0.32923(10) 0.3465(4) 0.2449(2) 0.0521(11) Uani 1 1 d . . . . .
H26A H 0.329286 0.287194 0.209460 0.063 Uiso 1 1 calc R U . . .
H26B H 0.306233 0.364900 0.237646 0.063 Uiso 1 1 calc R U . . .
C31 C 0.39198(12) 0.0028(4) 0.3941(3) 0.0670(14) Uani 1 1 d . . . . .
H31A H 0.371740 -0.001944 0.347122 0.080 Uiso 1 1 calc R U . . .
C32 C 0.39928(9) 0.0943(3) 0.4362(2) 0.0358(8) Uani 1 1 d . . . . .
C33 C 0.42825(9) 0.1027(3) 0.5050(2) 0.0378(9) Uani 1 1 d . . . . .
H33A H 0.433623 0.165655 0.535686 0.045 Uiso 1 1 calc R U . . .
C34 C 0.44935(9) 0.0176(3) 0.5284(2) 0.0403(9) Uani 1 1 d . . . . .
C35 C 0.44038(11) -0.0714(4) 0.4816(3) 0.0609(12) Uani 1 1 d . . . . .
C36 C 0.48186(10) 0.0244(4) 0.6024(2) 0.0493(11) Uani 1 1 d . . . . .
C37 C 0.46158(14) -0.1629(4) 0.5008(3) 0.0859(18) Uani 1 1 d . . . . .
S2 S 0.33178(2) 1.00837(7) 0.68054(6) 0.0388(2) Uani 1 1 d . . . . .
F2 F 0.25655(18) 1.3354(6) 0.5772(4) 0.042(3) Uani 0.274(6) 1 d . . P A 1
F3 F 0.30555(8) 1.3317(2) 0.86792(17) 0.0513(11) Uani 0.726(6) 1 d . . P A 2
O21 O 0.23672(7) 1.3628(2) 0.77127(17) 0.0524(7) Uani 1 1 d . . . . .
O22 O 0.44209(7) 1.1484(3) 0.7116(2) 0.0851(12) Uani 1 1 d . . . . .
N21 N 0.23818(8) 1.4798(3) 0.6777(2) 0.0475(9) Uani 1 1 d . . . . .
H2 H 0.2477(10) 1.491(3) 0.644(2) 0.057(12) Uiso 1 1 d . . . . .
N22 N 0.36425(7) 1.1917(2) 0.71609(17) 0.0351(7) Uani 1 1 d . . . . .
N23 N 0.39402(7) 1.0624(3) 0.69788(19) 0.0429(8) Uani 1 1 d . . . . .
C41 C 0.33611(8) 1.2465(3) 0.7187(2) 0.0333(8) Uani 1 1 d . . . . .
C42 C 0.33441(9) 1.2662(3) 0.7933(2) 0.0378(9) Uani 1 1 d . . . . .
H42A H 0.352051 1.246045 0.842727 0.045 Uiso 1 1 calc R U . . .
C43 C 0.30662(10) 1.3156(3) 0.7938(2) 0.0391(9) Uani 1 1 d . . . . .
H43A H 0.305367 1.328622 0.844677 0.047 Uiso 0.274(6) 1 calc R U P A 1
C44 C 0.28035(9) 1.3472(3) 0.7235(2) 0.0353(8) Uani 1 1 d . . . . .
C45 C 0.28311(9) 1.3264(3) 0.6499(2) 0.0375(9) Uani 1 1 d . . . . .
H45A H 0.265565 1.346892 0.600345 0.045 Uiso 0.726(6) 1 calc R U P A 2
C46 C 0.31066(8) 1.2769(3) 0.6473(2) 0.0363(9) Uani 1 1 d . . . . .
H46A H 0.312049 1.263921 0.596532 0.044 Uiso 1 1 calc R U . . .
C47 C 0.24967(9) 1.3981(3) 0.7266(2) 0.0415(9) Uani 1 1 d . . . . .
C48 C 0.20792(11) 1.5346(4) 0.6682(3) 0.0629(13) Uani 1 1 d . . . . .
H48A H 0.207256 1.602156 0.641809 0.094 Uiso 1 1 calc R U . . .
H48B H 0.207462 1.546066 0.721878 0.094 Uiso 1 1 calc R U . . .
H48C H 0.188565 1.492724 0.634638 0.094 Uiso 1 1 calc R U . . .
C51 C 0.36297(8) 1.0892(3) 0.6980(2) 0.0349(8) Uani 1 1 d . . . . .
C52 C 0.39585(9) 1.2408(3) 0.7266(2) 0.0428(9) Uani 1 1 d . . . . .
C53 C 0.41468(9) 1.1493(4) 0.7125(3) 0.0543(11) Uani 1 1 d . . . . .
C54 C 0.39637(9) 1.3394(3) 0.6768(2) 0.0421(9) Uani 1 1 d . . . . .
H54A H 0.402845 1.325106 0.630802 0.051 Uiso 1 1 calc R U . . .
H54B H 0.375602 1.381078 0.658856 0.051 Uiso 1 1 calc R U . . .
C55 C 0.42469(10) 1.3837(4) 0.7522(3) 0.0592(12) Uani 1 1 d . . . . .
H55A H 0.421320 1.457363 0.764097 0.071 Uiso 1 1 calc R U . . .
H55B H 0.447105 1.373422 0.752159 0.071 Uiso 1 1 calc R U . . .
C56 C 0.41588(11) 1.3039(4) 0.8051(3) 0.0629(13) Uani 1 1 d . . . . .
H56A H 0.401989 1.333098 0.832192 0.076 Uiso 1 1 calc R U . . .
H56B H 0.435388 1.266037 0.844341 0.076 Uiso 1 1 calc R U . . .
N24 N 0.44643(17) 0.8346(6) 0.7476(5) 0.0440(18) Uani 0.477(2) 1 d . . P B 3
C61 C 0.4346(2) 0.9284(8) 0.7532(6) 0.037(2) Uani 0.477(2) 1 d . . P B 3
H61A H 0.446098 0.967757 0.801290 0.044 Uiso 0.477(2) 1 calc R U P B 3
C62 C 0.4065(5) 0.9730(17) 0.6936(11) 0.031(4) Uani 0.477(2) 1 d . . P B 3
C63 C 0.3900(4) 0.9199(13) 0.6230(9) 0.033(4) Uani 0.477(2) 1 d . . P B 3
H63A H 0.371419 0.949520 0.579909 0.040 Uiso 0.477(2) 1 calc R U P B 3
C64 C 0.4017(4) 0.8192(10) 0.6165(7) 0.038(3) Uani 0.477(2) 1 d . . P B 3
C65 C 0.4285(7) 0.7906(17) 0.681(2) 0.038(10) Uani 0.477(2) 1 d . . P B 3
C66 C 0.3835(3) 0.7571(10) 0.5406(7) 0.057(3) Uani 0.477(2) 1 d . . P B 3
F21 F 0.37253(18) 0.6670(5) 0.5561(4) 0.099(2) Uani 0.477(2) 1 d . . P B 3
F22 F 0.35768(14) 0.8075(6) 0.4862(4) 0.086(2) Uani 0.477(2) 1 d . . P B 3
F23 F 0.40333(13) 0.7307(5) 0.5024(3) 0.0682(16) Uani 0.477(2) 1 d . . P B 3
C67 C 0.4426(3) 0.6771(8) 0.6801(7) 0.054(2) Uani 0.477(2) 1 d . . P B 3
N25 N 0.4515(2) 0.5950(7) 0.6750(6) 0.077(3) Uani 0.477(2) 1 d . . P B 3
N34 N 0.3802(2) 0.8187(7) 0.5636(7) 0.058(2) Uani 0.523(2) 1 d . . P B 4
C71 C 0.3765(3) 0.9109(14) 0.5904(9) 0.044(4) Uani 0.523(2) 1 d . . P B 4
H71A H 0.358075 0.952281 0.557252 0.053 Uiso 0.523(2) 1 calc R U P B 4
C72 C 0.3980(4) 0.9517(13) 0.6643(9) 0.027(4) Uani 0.523(2) 1 d . . P B 4
C73 C 0.4248(3) 0.8938(7) 0.7138(6) 0.037(2) Uani 0.523(2) 1 d . . P B 4
H73A H 0.439713 0.920645 0.764672 0.045 Uiso 0.523(2) 1 calc R U P B 4
C74 C 0.4302(6) 0.784(2) 0.685(2) 0.059(12) Uani 0.523(2) 1 d . . P B 4
C75 C 0.4058(3) 0.7620(10) 0.6114(10) 0.063(4) Uani 0.523(2) 1 d . . P B 4
C76 C 0.4581(3) 0.7286(7) 0.7391(8) 0.063(3) Uani 0.523(2) 1 d . . P B 4
F31 F 0.47641(13) 0.7012(4) 0.6965(3) 0.0802(17) Uani 0.523(2) 1 d . . P B 4
F32 F 0.47679(16) 0.7721(4) 0.8060(4) 0.0913(19) Uani 0.523(2) 1 d . . P B 4
F33 F 0.44790(17) 0.6364(4) 0.7567(5) 0.108(2) Uani 0.523(2) 1 d . . P B 4
C77A C 0.4094(5) 0.6476(14) 0.5941(11) 0.042(4) Uani 0.291(3) 1 d . . P B 4
C77B C 0.4053(6) 0.6761(19) 0.5572(15) 0.042(4) Uani 0.233(3) 1 d . . P B 4
N35A N 0.4108(4) 0.5643(11) 0.5731(10) 0.063(4) Uani 0.291(3) 1 d . . P B 4
N35B N 0.4065(5) 0.6022(14) 0.5230(13) 0.063(4) Uani 0.233(3) 1 d . . P B 4
O1 O 0.42361(8) 0.3516(3) 0.51014(19) 0.0708(9) Uani 1 1 d . . . . .
C1 C 0.44968(12) 0.3970(4) 0.5298(3) 0.0739(15) Uani 1 1 d D . . . .
C2 C 0.47688(13) 0.3837(5) 0.6097(3) 0.101(2) Uani 1 1 d D . . . .
H2A H 0.470702 0.330616 0.640596 0.152 Uiso 1 1 calc R U . . .
H2B H 0.481141 0.450282 0.639243 0.152 Uiso 1 1 calc R U . . .
H2C H 0.497041 0.361448 0.602863 0.152 Uiso 1 1 calc R U . . .
C3A C 0.4530(3) 0.5075(10) 0.4995(9) 0.092(3) Uani 0.435(8) 1 d D . P C 5
H3AA H 0.431265 0.542190 0.478906 0.137 Uiso 0.435(8) 1 calc R U P C 5
H3AB H 0.461069 0.502329 0.455819 0.137 Uiso 0.435(8) 1 calc R U P C 5
H3AC H 0.468914 0.548249 0.544692 0.137 Uiso 0.435(8) 1 calc R U P C 5
C3B C 0.4608(2) 0.4347(10) 0.4601(6) 0.092(3) Uani 0.565(8) 1 d D . P C 6
H3BA H 0.450765 0.389137 0.412534 0.137 Uiso 0.565(8) 1 calc R U P C 6
H3BB H 0.485116 0.431399 0.479862 0.137 Uiso 0.565(8) 1 calc R U P C 6
H3BC H 0.453337 0.506771 0.444909 0.137 Uiso 0.565(8) 1 calc R U P C 6


_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 C21 1.651(3) . ?
F1 C13 1.350(4) . ?
F11 C36 1.324(5) . ?
F12 C36 1.337(4) . ?
F13 C36 1.338(4) . ?
O11 C17 1.235(4) . ?
O12 C23 1.206(4) . ?
N11 C17 1.321(5) . ?
N11 C18 1.464(4) . ?
N11 H1 0.84(4) . ?
N12 C21 1.334(4) . ?
N12 C11 1.436(4) . ?
N12 C22 1.464(4) . ?
N13 C21 1.394(4) . ?
N13 C23 1.395(4) . ?
N13 C32 1.422(4) . ?
N14 C35 1.335(6) . ?
N14 C31 1.337(5) . ?
N15 C37 1.143(6) . ?
C11 C12 1.373(5) . ?
C11 C16 1.377(5) . ?
C12 C13 1.372(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.371(5) . ?
C14 C15 1.384(5) . ?
C14 C17 1.504(5) . ?
C15 C16 1.391(5) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C22 C23 1.505(5) . ?
C22 C24 1.536(5) . ?
C22 C26 1.543(5) . ?
C24 C25 1.534(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.534(6) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C31 C32 1.359(5) . ?
C31 H31A 0.9500 . ?
C32 C33 1.375(5) . ?
C33 C34 1.380(5) . ?
C33 H33A 0.9500 . ?
C34 C35 1.374(6) . ?
C34 C36 1.512(5) . ?
C35 C37 1.448(6) . ?
S2 C51 1.640(4) . ?
F2 C45 1.361(8) . ?
F3 C43 1.363(4) . ?
O21 C47 1.235(4) . ?
O22 C53 1.205(4) . ?
N21 C47 1.328(5) . ?
N21 C48 1.447(5) . ?
N21 H2 0.87(4) . ?
N22 C51 1.347(5) . ?
N22 C41 1.433(4) . ?
N22 C52 1.461(4) . ?
N23 C62 1.28(2) . ?
N23 C53 1.390(5) . ?
N23 C51 1.401(4) . ?
N23 C72 1.575(16) . ?
C41 C46 1.375(5) . ?
C41 C42 1.391(5) . ?
C42 C43 1.373(5) . ?
C42 H42A 0.9500 . ?
C43 C44 1.384(5) . ?
C43 H43A 0.9500 . ?
C44 C45 1.397(5) . ?
C44 C47 1.513(5) . ?
C45 C46 1.378(5) . ?
C45 H45A 0.9500 . ?
C46 H46A 0.9500 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C52 C53 1.510(6) . ?
C52 C54 1.550(5) . ?
C52 C56 1.553(6) . ?
C54 C55 1.532(5) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C55 C56 1.541(5) . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C56 H56A 0.9900 . ?
C56 H56B 0.9900 . ?
N24 C65 1.26(4) . ?
N24 C61 1.326(14) . ?
C61 C62 1.39(3) . ?
C61 H61A 0.9500 . ?
C62 C63 1.361(15) . ?
C63 C64 1.41(2) . ?
C63 H63A 0.9500 . ?
C64 C65 1.33(3) . ?
C64 C66 1.500(15) . ?
C65 C67 1.58(2) . ?
C66 F21 1.320(12) . ?
C66 F22 1.327(14) . ?
C66 F23 1.345(11) . ?
C67 N25 1.137(12) . ?
N34 C71 1.31(2) . ?
N34 C75 1.321(18) . ?
C71 C72 1.383(14) . ?
C71 H71A 0.9500 . ?
C72 C73 1.37(2) . ?
C73 C74 1.54(3) . ?
C73 H73A 0.9500 . ?
C74 C75 1.36(4) . ?
C74 C76 1.41(3) . ?
C75 C77B 1.46(3) . ?
C75 C77A 1.52(2) . ?
C76 F32 1.278(13) . ?
C76 F33 1.341(9) . ?
C76 F31 1.355(10) . ?
C77A N35A 1.14(2) . ?
C77B N35B 1.14(3) . ?
O1 C1 1.201(5) . ?
C1 C2 1.462(6) . ?
C1 C3A 1.541(11) . ?
C1 C3B 1.583(9) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 0.9800 . ?
C3B H3BA 0.9800 . ?
C3B H3BB 0.9800 . ?
C3B H3BC 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
C17 N11 C18 121.2(3) . . ?
C17 N11 H1 121(3) . . ?
C18 N11 H1 117(3) . . ?
C21 N12 C11 123.2(3) . . ?
C21 N12 C22 113.4(3) . . ?
C11 N12 C22 122.9(3) . . ?
C21 N13 C23 111.0(3) . . ?
C21 N13 C32 125.3(3) . . ?
C23 N13 C32 123.3(3) . . ?
C35 N14 C31 117.1(4) . . ?
C12 C11 C16 121.3(3) . . ?
C12 C11 N12 118.3(3) . . ?
C16 C11 N12 120.3(3) . . ?
C13 C12 C11 118.0(4) . . ?
C13 C12 H12A 121.0 . . ?
C11 C12 H12A 121.0 . . ?
F1 C13 C14 118.5(3) . . ?
F1 C13 C12 118.2(4) . . ?
C14 C13 C12 123.2(4) . . ?
C13 C14 C15 117.7(3) . . ?
C13 C14 C17 120.1(3) . . ?
C15 C14 C17 122.2(3) . . ?
C14 C15 C16 120.7(4) . . ?
C14 C15 H15A 119.6 . . ?
C16 C15 H15A 119.6 . . ?
C11 C16 C15 119.1(4) . . ?
C11 C16 H16A 120.5 . . ?
C15 C16 H16A 120.5 . . ?
O11 C17 N11 123.8(3) . . ?
O11 C17 C14 120.3(4) . . ?
N11 C17 C14 116.0(3) . . ?
N11 C18 H18A 109.5 . . ?
N11 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N11 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N12 C21 N13 107.4(3) . . ?
N12 C21 S1 127.8(3) . . ?
N13 C21 S1 124.8(3) . . ?
N12 C22 C23 101.1(3) . . ?
N12 C22 C24 120.5(3) . . ?
C23 C22 C24 114.5(3) . . ?
N12 C22 C26 119.7(3) . . ?
C23 C22 C26 113.1(3) . . ?
C24 C22 C26 88.6(3) . . ?
O12 C23 N13 124.8(3) . . ?
O12 C23 C22 128.2(3) . . ?
N13 C23 C22 107.0(3) . . ?
C25 C24 C22 88.8(3) . . ?
C25 C24 H24A 113.8 . . ?
C22 C24 H24A 113.8 . . ?
C25 C24 H24B 113.8 . . ?
C22 C24 H24B 113.8 . . ?
H24A C24 H24B 111.1 . . ?
C24 C25 C26 89.0(3) . . ?
C24 C25 H25A 113.8 . . ?
C26 C25 H25A 113.8 . . ?
C24 C25 H25B 113.8 . . ?
C26 C25 H25B 113.8 . . ?
H25A C25 H25B 111.0 . . ?
C25 C26 C22 88.5(3) . . ?
C25 C26 H26A 113.9 . . ?
C22 C26 H26A 113.9 . . ?
C25 C26 H26B 113.9 . . ?
C22 C26 H26B 113.9 . . ?
H26A C26 H26B 111.1 . . ?
N14 C31 C32 123.0(4) . . ?
N14 C31 H31A 118.5 . . ?
C32 C31 H31A 118.5 . . ?
C31 C32 C33 119.6(4) . . ?
C31 C32 N13 118.7(3) . . ?
C33 C32 N13 121.7(3) . . ?
C32 C33 C34 118.4(4) . . ?
C32 C33 H33A 120.8 . . ?
C34 C33 H33A 120.8 . . ?
C35 C34 C33 118.3(4) . . ?
C35 C34 C36 121.5(4) . . ?
C33 C34 C36 120.1(4) . . ?
N14 C35 C34 123.5(4) . . ?
N14 C35 C37 114.9(4) . . ?
C34 C35 C37 121.6(4) . . ?
F11 C36 F12 107.4(4) . . ?
F11 C36 F13 108.6(3) . . ?
F12 C36 F13 105.2(3) . . ?
F11 C36 C34 112.7(3) . . ?
F12 C36 C34 111.7(3) . . ?
F13 C36 C34 110.9(3) . . ?
N15 C37 C35 177.5(6) . . ?
C47 N21 C48 123.1(3) . . ?
C47 N21 H2 116(3) . . ?
C48 N21 H2 120(3) . . ?
C51 N22 C41 122.0(3) . . ?
C51 N22 C52 113.3(3) . . ?
C41 N22 C52 124.5(3) . . ?
C62 N23 C53 117.6(9) . . ?
C62 N23 C51 130.8(9) . . ?
C53 N23 C51 111.3(3) . . ?
C53 N23 C72 128.9(6) . . ?
C51 N23 C72 118.3(6) . . ?
C46 C41 C42 120.5(3) . . ?
C46 C41 N22 119.8(3) . . ?
C42 C41 N22 119.7(3) . . ?
C43 C42 C41 118.4(3) . . ?
C43 C42 H42A 120.8 . . ?
C41 C42 H42A 120.8 . . ?
F3 C43 C42 116.7(4) . . ?
F3 C43 C44 120.2(3) . . ?
C42 C43 C44 123.1(3) . . ?
C42 C43 H43A 118.5 . . ?
C44 C43 H43A 118.5 . . ?
C43 C44 C45 116.7(3) . . ?
C43 C44 C47 121.4(3) . . ?
C45 C44 C47 121.9(3) . . ?
F2 C45 C46 115.6(4) . . ?
F2 C45 C44 121.6(4) . . ?
C46 C45 C44 121.7(4) . . ?
C46 C45 H45A 119.2 . . ?
C44 C45 H45A 119.2 . . ?
C41 C46 C45 119.6(3) . . ?
C41 C46 H46A 120.2 . . ?
C45 C46 H46A 120.2 . . ?
O21 C47 N21 124.4(4) . . ?
O21 C47 C44 120.6(3) . . ?
N21 C47 C44 115.0(3) . . ?
N21 C48 H48A 109.5 . . ?
N21 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
N21 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
N22 C51 N23 106.9(3) . . ?
N22 C51 S2 127.7(3) . . ?
N23 C51 S2 125.4(3) . . ?
N22 C52 C53 101.3(3) . . ?
N22 C52 C54 120.4(3) . . ?
C53 C52 C54 113.6(3) . . ?
N22 C52 C56 120.3(3) . . ?
C53 C52 C56 113.9(3) . . ?
C54 C52 C56 88.0(3) . . ?
O22 C53 N23 124.5(4) . . ?
O22 C53 C52 128.4(4) . . ?
N23 C53 C52 107.1(3) . . ?
C55 C54 C52 89.2(3) . . ?
C55 C54 H54A 113.8 . . ?
C52 C54 H54A 113.8 . . ?
C55 C54 H54B 113.8 . . ?
C52 C54 H54B 113.8 . . ?
H54A C54 H54B 111.0 . . ?
C54 C55 C56 89.1(3) . . ?
C54 C55 H55A 113.8 . . ?
C56 C55 H55A 113.8 . . ?
C54 C55 H55B 113.8 . . ?
C56 C55 H55B 113.8 . . ?
H55A C55 H55B 111.0 . . ?
C55 C56 C52 88.7(3) . . ?
C55 C56 H56A 113.9 . . ?
C52 C56 H56A 113.9 . . ?
C55 C56 H56B 113.9 . . ?
C52 C56 H56B 113.9 . . ?
H56A C56 H56B 111.1 . . ?
C65 N24 C61 111.0(12) . . ?
N24 C61 C62 124.5(12) . . ?
N24 C61 H61A 117.8 . . ?
C62 C61 H61A 117.8 . . ?
N23 C62 C63 115(2) . . ?
N23 C62 C61 126.0(11) . . ?
C63 C62 C61 119(2) . . ?
C62 C63 C64 117.3(18) . . ?
C62 C63 H63A 121.3 . . ?
C64 C63 H63A 121.3 . . ?
C65 C64 C63 113.7(16) . . ?
C65 C64 C66 127.6(19) . . ?
C63 C64 C66 118.7(15) . . ?
N24 C65 C64 134.3(17) . . ?
N24 C65 C67 109(2) . . ?
C64 C65 C67 117(3) . . ?
F21 C66 F22 107.7(9) . . ?
F21 C66 F23 104.5(10) . . ?
F22 C66 F23 106.4(8) . . ?
F21 C66 C64 112.2(9) . . ?
F22 C66 C64 113.4(13) . . ?
F23 C66 C64 112.0(10) . . ?
N25 C67 C65 176.3(19) . . ?
C71 N34 C75 116.9(14) . . ?
N34 C71 C72 123.7(15) . . ?
N34 C71 H71A 118.1 . . ?
C72 C71 H71A 118.1 . . ?
C73 C72 C71 119.6(14) . . ?
C73 C72 N23 115.8(11) . . ?
C71 C72 N23 124.6(14) . . ?
C72 C73 C74 118.8(14) . . ?
C72 C73 H73A 120.6 . . ?
C74 C73 H73A 120.6 . . ?
C75 C74 C76 134(2) . . ?
C75 C74 C73 110.3(19) . . ?
C76 C74 C73 116(2) . . ?
N34 C75 C74 130.6(18) . . ?
N34 C75 C77B 101.4(16) . . ?
C74 C75 C77B 126.9(18) . . ?
N34 C75 C77A 121.8(15) . . ?
C74 C75 C77A 107.1(16) . . ?
C77B C75 C77A 27.5(9) . . ?
F32 C76 F33 108.2(10) . . ?
F32 C76 F31 109.7(9) . . ?
F33 C76 F31 103.3(7) . . ?
F32 C76 C74 118.7(14) . . ?
F33 C76 C74 109.0(13) . . ?
F31 C76 C74 106.9(15) . . ?
N35A C77A C75 173(2) . . ?
N35B C77B C75 172(3) . . ?
O1 C1 C2 122.5(5) . . ?
O1 C1 C3A 123.6(6) . . ?
C2 C1 C3A 107.2(7) . . ?
O1 C1 C3B 118.1(6) . . ?
C2 C1 C3B 114.9(5) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3A H3AA 109.5 . . ?
C1 C3A H3AB 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
C1 C3A H3AC 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
C1 C3B H3BA 109.5 . . ?
C1 C3B H3BB 109.5 . . ?
H3BA C3B H3BB 109.5 . . ?
C1 C3B H3BC 109.5 . . ?
H3BA C3B H3BC 109.5 . . ?
H3BB C3B H3BC 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
C21 N12 C11 C12 81.9(4) . . . . ?
C22 N12 C11 C12 -89.3(4) . . . . ?
C21 N12 C11 C16 -99.2(4) . . . . ?
C22 N12 C11 C16 89.6(4) . . . . ?
C16 C11 C12 C13 2.0(6) . . . . ?
N12 C11 C12 C13 -179.2(3) . . . . ?
C11 C12 C13 F1 -178.0(3) . . . . ?
C11 C12 C13 C14 -1.3(6) . . . . ?
F1 C13 C14 C15 176.8(3) . . . . ?
C12 C13 C14 C15 0.1(6) . . . . ?
F1 C13 C14 C17 -5.3(5) . . . . ?
C12 C13 C14 C17 178.0(3) . . . . ?
C13 C14 C15 C16 0.4(5) . . . . ?
C17 C14 C15 C16 -177.4(3) . . . . ?
C12 C11 C16 C15 -1.5(6) . . . . ?
N12 C11 C16 C15 179.7(3) . . . . ?
C14 C15 C16 C11 0.2(6) . . . . ?
C18 N11 C17 O11 -1.4(6) . . . . ?
C18 N11 C17 C14 179.4(3) . . . . ?
C13 C14 C17 O11 -54.9(5) . . . . ?
C15 C14 C17 O11 122.8(4) . . . . ?
C13 C14 C17 N11 124.3(4) . . . . ?
C15 C14 C17 N11 -57.9(5) . . . . ?
C11 N12 C21 N13 -172.6(3) . . . . ?
C22 N12 C21 N13 -0.7(4) . . . . ?
C11 N12 C21 S1 8.8(5) . . . . ?
C22 N12 C21 S1 -179.2(3) . . . . ?
C23 N13 C21 N12 2.8(4) . . . . ?
C32 N13 C21 N12 175.2(3) . . . . ?
C23 N13 C21 S1 -178.6(3) . . . . ?
C32 N13 C21 S1 -6.3(5) . . . . ?
C21 N12 C22 C23 -1.5(4) . . . . ?
C11 N12 C22 C23 170.5(3) . . . . ?
C21 N12 C22 C24 -128.8(3) . . . . ?
C11 N12 C22 C24 43.2(5) . . . . ?
C21 N12 C22 C26 123.5(4) . . . . ?
C11 N12 C22 C26 -64.5(5) . . . . ?
C21 N13 C23 O12 178.3(4) . . . . ?
C32 N13 C23 O12 5.7(6) . . . . ?
C21 N13 C23 C22 -3.7(4) . . . . ?
C32 N13 C23 C22 -176.3(3) . . . . ?
N12 C22 C23 O12 -179.0(4) . . . . ?
C24 C22 C23 O12 -47.9(5) . . . . ?
C26 C22 C23 O12 51.7(5) . . . . ?
N12 C22 C23 N13 3.0(4) . . . . ?
C24 C22 C23 N13 134.2(3) . . . . ?
C26 C22 C23 N13 -126.3(3) . . . . ?
N12 C22 C24 C25 -141.0(3) . . . . ?
C23 C22 C24 C25 98.1(3) . . . . ?
C26 C22 C24 C25 -16.8(3) . . . . ?
C22 C24 C25 C26 16.9(3) . . . . ?
C24 C25 C26 C22 -16.8(3) . . . . ?
N12 C22 C26 C25 141.7(3) . . . . ?
C23 C22 C26 C25 -99.3(3) . . . . ?
C24 C22 C26 C25 16.8(3) . . . . ?
C35 N14 C31 C32 -0.7(8) . . . . ?
N14 C31 C32 C33 -0.7(7) . . . . ?
N14 C31 C32 N13 176.2(4) . . . . ?
C21 N13 C32 C31 104.2(4) . . . . ?
C23 N13 C32 C31 -84.4(5) . . . . ?
C21 N13 C32 C33 -79.0(4) . . . . ?
C23 N13 C32 C33 92.4(4) . . . . ?
C31 C32 C33 C34 0.9(5) . . . . ?
N13 C32 C33 C34 -175.9(3) . . . . ?
C32 C33 C34 C35 0.2(5) . . . . ?
C32 C33 C34 C36 178.5(3) . . . . ?
C31 N14 C35 C34 1.9(8) . . . . ?
C31 N14 C35 C37 -178.1(5) . . . . ?
C33 C34 C35 N14 -1.7(7) . . . . ?
C36 C34 C35 N14 -180.0(4) . . . . ?
C33 C34 C35 C37 178.4(4) . . . . ?
C36 C34 C35 C37 0.1(7) . . . . ?
C35 C34 C36 F11 169.4(4) . . . . ?
C33 C34 C36 F11 -8.9(5) . . . . ?
C35 C34 C36 F12 48.3(5) . . . . ?
C33 C34 C36 F12 -129.9(4) . . . . ?
C35 C34 C36 F13 -68.6(4) . . . . ?
C33 C34 C36 F13 113.1(4) . . . . ?
C51 N22 C41 C46 -78.1(4) . . . . ?
C52 N22 C41 C46 97.3(4) . . . . ?
C51 N22 C41 C42 100.4(4) . . . . ?
C52 N22 C41 C42 -84.2(4) . . . . ?
C46 C41 C42 C43 0.7(5) . . . . ?
N22 C41 C42 C43 -177.7(3) . . . . ?
C41 C42 C43 F3 178.7(3) . . . . ?
C41 C42 C43 C44 -0.5(5) . . . . ?
F3 C43 C44 C45 -179.0(3) . . . . ?
C42 C43 C44 C45 0.1(5) . . . . ?
F3 C43 C44 C47 -1.2(5) . . . . ?
C42 C43 C44 C47 177.9(3) . . . . ?
C43 C44 C45 F2 167.2(5) . . . . ?
C47 C44 C45 F2 -10.6(6) . . . . ?
C43 C44 C45 C46 -0.1(5) . . . . ?
C47 C44 C45 C46 -177.8(3) . . . . ?
C42 C41 C46 C45 -0.7(5) . . . . ?
N22 C41 C46 C45 177.8(3) . . . . ?
F2 C45 C46 C41 -167.6(4) . . . . ?
C44 C45 C46 C41 0.3(5) . . . . ?
C48 N21 C47 O21 -2.9(6) . . . . ?
C48 N21 C47 C44 176.0(4) . . . . ?
C43 C44 C47 O21 -43.7(5) . . . . ?
C45 C44 C47 O21 134.0(4) . . . . ?
C43 C44 C47 N21 137.4(4) . . . . ?
C45 C44 C47 N21 -45.0(5) . . . . ?
C41 N22 C51 N23 177.8(3) . . . . ?
C52 N22 C51 N23 1.9(4) . . . . ?
C41 N22 C51 S2 -3.1(5) . . . . ?
C52 N22 C51 S2 -179.0(3) . . . . ?
C62 N23 C51 N22 170.8(11) . . . . ?
C53 N23 C51 N22 -2.6(4) . . . . ?
C72 N23 C51 N22 -169.9(7) . . . . ?
C62 N23 C51 S2 -8.3(12) . . . . ?
C53 N23 C51 S2 178.2(3) . . . . ?
C72 N23 C51 S2 11.0(8) . . . . ?
C51 N22 C52 C53 -0.5(4) . . . . ?
C41 N22 C52 C53 -176.3(3) . . . . ?
C51 N22 C52 C54 125.7(4) . . . . ?
C41 N22 C52 C54 -50.1(5) . . . . ?
C51 N22 C52 C56 -127.1(4) . . . . ?
C41 N22 C52 C56 57.1(5) . . . . ?
C62 N23 C53 O22 9.3(11) . . . . ?
C51 N23 C53 O22 -176.3(4) . . . . ?
C72 N23 C53 O22 -10.7(10) . . . . ?
C62 N23 C53 C52 -172.1(10) . . . . ?
C51 N23 C53 C52 2.3(4) . . . . ?
C72 N23 C53 C52 167.9(8) . . . . ?
N22 C52 C53 O22 177.5(4) . . . . ?
C54 C52 C53 O22 46.9(6) . . . . ?
C56 C52 C53 O22 -51.9(6) . . . . ?
N22 C52 C53 N23 -1.1(4) . . . . ?
C54 C52 C53 N23 -131.7(3) . . . . ?
C56 C52 C53 N23 129.6(3) . . . . ?
N22 C52 C54 C55 141.1(4) . . . . ?
C53 C52 C54 C55 -98.6(4) . . . . ?
C56 C52 C54 C55 16.8(3) . . . . ?
C52 C54 C55 C56 -16.9(3) . . . . ?
C54 C55 C56 C52 16.9(3) . . . . ?
N22 C52 C56 C55 -141.1(4) . . . . ?
C53 C52 C56 C55 98.3(4) . . . . ?
C54 C52 C56 C55 -16.7(3) . . . . ?
C65 N24 C61 C62 -0.9(19) . . . . ?
C53 N23 C62 C63 -123.4(15) . . . . ?
C51 N23 C62 C63 63(2) . . . . ?
C53 N23 C62 C61 56(2) . . . . ?
C51 N23 C62 C61 -116.8(15) . . . . ?
N24 C61 C62 N23 178.3(13) . . . . ?
N24 C61 C62 C63 -2(3) . . . . ?
N23 C62 C63 C64 -177.1(12) . . . . ?
C61 C62 C63 C64 3(3) . . . . ?
C62 C63 C64 C65 -2(2) . . . . ?
C62 C63 C64 C66 178.1(14) . . . . ?
C61 N24 C65 C64 3(3) . . . . ?
C61 N24 C65 C67 -177.0(10) . . . . ?
C63 C64 C65 N24 -2(3) . . . . ?
C66 C64 C65 N24 178.6(18) . . . . ?
C63 C64 C65 C67 178.3(13) . . . . ?
C66 C64 C65 C67 -1(2) . . . . ?
C65 C64 C66 F21 58.1(19) . . . . ?
C63 C64 C66 F21 -121.6(12) . . . . ?
C65 C64 C66 F22 -179.6(14) . . . . ?
C63 C64 C66 F22 0.8(13) . . . . ?
C65 C64 C66 F23 -59.1(18) . . . . ?
C63 C64 C66 F23 121.2(13) . . . . ?
C75 N34 C71 C72 1.1(19) . . . . ?
N34 C71 C72 C73 0(2) . . . . ?
N34 C71 C72 N23 -180.0(11) . . . . ?
C53 N23 C72 C73 65.8(14) . . . . ?
C51 N23 C72 C73 -129.5(9) . . . . ?
C53 N23 C72 C71 -114.6(13) . . . . ?
C51 N23 C72 C71 50.1(16) . . . . ?
C71 C72 C73 C74 0(2) . . . . ?
N23 C72 C73 C74 179.6(12) . . . . ?
C72 C73 C74 C75 0(2) . . . . ?
C72 C73 C74 C76 -179.7(14) . . . . ?
C71 N34 C75 C74 -2(2) . . . . ?
C71 N34 C75 C77B -170.6(13) . . . . ?
C71 N34 C75 C77A 169.4(12) . . . . ?
C76 C74 C75 N34 -179.5(17) . . . . ?
C73 C74 C75 N34 1(3) . . . . ?
C76 C74 C75 C77B -13(4) . . . . ?
C73 C74 C75 C77B 167.6(15) . . . . ?
C76 C74 C75 C77A 8(3) . . . . ?
C73 C74 C75 C77A -170.8(13) . . . . ?
C75 C74 C76 F32 -179.9(19) . . . . ?
C73 C74 C76 F32 -1(2) . . . . ?
C75 C74 C76 F33 -56(3) . . . . ?
C73 C74 C76 F33 123.5(14) . . . . ?
C75 C74 C76 F31 56(3) . . . . ?
C73 C74 C76 F31 -125.4(15) . . . . ?

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
_geom_hbond_publ_flag
N11 H1 O21 0.84(4) 2.10(4) 2.940(4) 177(4) 6_575 yes
N21 H2 O11 0.87(4) 1.96(4) 2.794(4) 160(4) 1_565 yes

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_KA1165_0m_APA-DMA-1-1
_database_code_depnum_ccdc_archive 'CCDC 2152153'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-02-15 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            Apalutamide-dimethylacetamide-1:1
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 F4 N5 O2 S, C4 H9 N O'
_chemical_formula_sum            'C25 H24 F4 N6 O3 S'
_chemical_formula_weight         564.56

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                   22.5794(15)
_cell_length_b                   13.3362(7)
_cell_length_c                   18.2192(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.944(2)
_cell_angle_gamma                90
_cell_volume                     5485.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9843
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.68

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             2336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.183
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6281
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS 2014/5'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50692
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.236
_diffrn_reflns_theta_max         26.249
_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             11078
_reflns_number_gt                7054
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0598P)²+2.9625P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         11078
_refine_ls_number_parameters     894
_refine_ls_number_restraints     423
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1671
_refine_ls_wR_factor_gt          0.1424
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.004
_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
C1A C 0.23887(12) 1.1582(2) 0.28614(14) 0.0502(7) Uani 1 1 d . . . . .
C2A C 0.18874(12) 1.1487(2) 0.32706(16) 0.0563(7) Uani 1 1 d . . . . .
H2A H 0.180898 1.089442 0.352024 0.068 Uiso 1 1 calc R U . . .
C3A C 0.15017(12) 1.2287(2) 0.33046(15) 0.0555(7) Uani 1 1 d . . . . .
C4A C 0.16440(14) 1.3150(2) 0.29230(18) 0.0634(8) Uani 1 1 d . . . . .
C5A C 0.24886(14) 1.2464(2) 0.25000(19) 0.0698(9) Uani 1 1 d . . . . .
H5A H 0.282944 1.251696 0.222290 0.084 Uiso 1 1 calc R U . . .
C6A C 0.31550(12) 1.0383(2) 0.33370(14) 0.0492(6) Uani 1 1 d . . . . .
C7A C 0.32307(13) 0.9330(2) 0.23124(14) 0.0568(7) Uani 1 1 d . . . . .
C8A C 0.28085(14) 1.0176(2) 0.21549(16) 0.0613(8) Uani 1 1 d . . . . .
C9A C 0.09478(15) 1.2211(3) 0.3733(2) 0.0759(9) Uani 1 1 d . . . . .
C10A C 0.12798(17) 1.4046(3) 0.2958(2) 0.0898(11) Uani 1 1 d . . . . .
C11A C 0.37973(12) 0.89260(19) 0.34936(14) 0.0474(6) Uani 1 1 d . . . . .
C12A C 0.35439(13) 0.8242(2) 0.39589(15) 0.0574(7) Uani 1 1 d . . . . .
H12 H 0.313464 0.819827 0.399878 0.069 Uiso 1 1 calc R U . . .
C13A C 0.39116(13) 0.7627(2) 0.43623(15) 0.0571(7) Uani 1 1 d . . . . .
H131 H 0.374195 0.717869 0.468842 0.068 Uiso 0.121(3) 1 calc R U P A 2
C14A C 0.45175(12) 0.76402(19) 0.43088(14) 0.0486(6) Uani 1 1 d . . . . .
C15A C 0.47525(13) 0.8323(2) 0.38327(18) 0.0623(8) Uani 1 1 d . . . . .
H15A H 0.516117 0.834898 0.378020 0.075 Uiso 0.879(3) 1 calc R U P A 1
C16A C 0.44004(13) 0.8975(2) 0.34278(17) 0.0608(8) Uani 1 1 d . . . . .
H16 H 0.457054 0.944094 0.311523 0.073 Uiso 1 1 calc R U . . .
C17A C 0.36980(17) 0.9150(3) 0.17221(19) 0.0903(12) Uani 1 1 d . . . . .
H17A H 0.373806 0.970138 0.137960 0.108 Uiso 1 1 calc R U . . .
H17B H 0.408115 0.894512 0.191874 0.108 Uiso 1 1 calc R U . . .
C18A C 0.29788(16) 0.8285(2) 0.21281(17) 0.0721(9) Uani 1 1 d . . . . .
H18A H 0.310108 0.776682 0.247239 0.087 Uiso 1 1 calc R U . . .
H18B H 0.255284 0.827706 0.204989 0.087 Uiso 1 1 calc R U . . .
C19A C 0.3326(2) 0.8288(4) 0.1427(2) 0.1115(15) Uani 1 1 d . . . . .
H19A H 0.309052 0.846023 0.099501 0.134 Uiso 1 1 calc R U . . .
H19B H 0.354964 0.767791 0.134783 0.134 Uiso 1 1 calc R U . . .
C20A C 0.48936(14) 0.6954(2) 0.47769(16) 0.0559(7) Uani 1 1 d . . . . .
C21A C 0.56801(16) 0.5712(3) 0.4806(2) 0.0792(10) Uani 1 1 d . . . . .
H21A H 0.559123 0.502586 0.468758 0.119 Uiso 1 1 calc R U . . .
H21B H 0.564949 0.580921 0.532625 0.119 Uiso 1 1 calc R U . . .
H21C H 0.607528 0.586684 0.465655 0.119 Uiso 1 1 calc R U . . .
S1A S 0.32550(4) 1.08892(6) 0.41494(4) 0.0709(3) Uani 1 1 d . . . . .
F1A F 0.08777(17) 1.1293(3) 0.4024(3) 0.1427(15) Uani 0.879(3) 1 d . U P A 1
F2A F 0.09478(15) 1.2792(4) 0.4311(2) 0.1439(15) Uani 0.879(3) 1 d . U P A 1
F3A F 0.04722(12) 1.2368(5) 0.3371(2) 0.154(2) Uani 0.879(3) 1 d . U P A 1
F11 F 0.1057(7) 1.187(2) 0.4315(8) 0.071(4) Uani 0.121(3) 1 d . U P A 2
F21 F 0.0635(9) 1.305(2) 0.3752(15) 0.109(5) Uani 0.121(3) 1 d . U P A 2
F31 F 0.0611(7) 1.1544(19) 0.3350(14) 0.095(5) Uani 0.121(3) 1 d . U P A 2
F4A F 0.36664(10) 0.69751(19) 0.48182(13) 0.0960(8) Uani 0.879(3) 1 d . . P A 1
F41 F 0.5198(8) 0.8441(14) 0.3840(9) 0.0960(8) Uani 0.121(3) 1 d . . P A 2
O1A O 0.25407(12) 1.0336(2) 0.15935(12) 0.0945(8) Uani 1 1 d . . . . .
O2A O 0.48456(12) 0.69496(18) 0.54484(11) 0.0885(8) Uani 1 1 d . . . . .
N1A N 0.21274(12) 1.3248(2) 0.25220(17) 0.0792(8) Uani 1 1 d . . . . .
N2A N 0.27928(10) 1.07689(17) 0.27779(11) 0.0521(6) Uani 1 1 d . . . . .
N3A N 0.34184(10) 0.95651(17) 0.30674(12) 0.0534(6) Uani 1 1 d . . . . .
N4A N 0.10158(19) 1.4766(3) 0.2992(3) 0.1376(16) Uani 1 1 d . . . . .
N5A N 0.52607(11) 0.63693(18) 0.44234(15) 0.0564(6) Uani 1 1 d . . . . .
H5NA H 0.5256(13) 0.636(2) 0.3956(18) 0.062(9) Uiso 1 1 d . . . . .
C1B C 0.22257(11) 1.2582(2) 0.54343(15) 0.0483(6) Uani 1 1 d . . . . .
C2B C 0.25308(12) 1.3135(2) 0.49288(16) 0.0535(7) Uani 1 1 d . . . . .
H2B H 0.285602 1.286535 0.469229 0.064 Uiso 1 1 calc R U . . .
C3B C 0.23435(13) 1.4101(2) 0.47799(16) 0.0562(7) Uani 1 1 d . . . . .
C4B C 0.18473(14) 1.4447(2) 0.51520(18) 0.0609(8) Uani 1 1 d . . . . .
C5B C 0.17264(12) 1.2973(2) 0.57540(16) 0.0571(7) Uani 1 1 d . . . . .
H5B H 0.151677 1.257786 0.608017 0.069 Uiso 1 1 calc R U . . .
C6B C 0.29922(11) 1.13764(19) 0.58953(13) 0.0439(6) Uani 1 1 d . . . . .
C7B C 0.24276(12) 0.9896(2) 0.58956(16) 0.0538(7) Uani 1 1 d . . . . .
C8B C 0.20592(12) 1.0757(2) 0.56223(17) 0.0587(7) Uani 1 1 d . . . . .
C9B C 0.26761(18) 1.4736(3) 0.4267(2) 0.0783(10) Uani 1 1 d . . . . .
C10B C 0.16385(19) 1.5466(3) 0.5079(2) 0.0885(11) Uani 1 1 d . . . . .
C11B C 0.35044(11) 0.98915(19) 0.63454(14) 0.0453(6) Uani 1 1 d . . . . .
C12B C 0.35560(12) 0.9715(2) 0.70897(15) 0.0533(7) Uani 1 1 d . . . . .
H12B H 0.325971 0.991677 0.740598 0.064 Uiso 1 1 calc R U . . .
C13B C 0.40529(13) 0.9236(2) 0.73541(14) 0.0536(7) Uani 1 1 d . . . . .
H132 H 0.408463 0.911265 0.785561 0.064 Uiso 0.225(5) 1 calc R U P B 2
C14B C 0.45074(12) 0.89290(19) 0.69108(14) 0.0472(6) Uani 1 1 d . . . . .
C15B C 0.44436(12) 0.9128(2) 0.61650(14) 0.0504(6) Uani 1 1 d . . . . .
H15B H 0.474261 0.893583 0.584952 0.060 Uiso 0.775(5) 1 calc R U P B 1
C16B C 0.39490(12) 0.9603(2) 0.58808(14) 0.0512(7) Uani 1 1 d . . . . .
H16B H 0.391540 0.972836 0.537973 0.061 Uiso 1 1 calc R U . . .
C17B C 0.21214(15) 0.9258(2) 0.64852(19) 0.0721(9) Uani 1 1 d . . . . .
H17C H 0.239235 0.897413 0.684803 0.087 Uiso 1 1 calc R U . . .
H17D H 0.179292 0.959313 0.671808 0.087 Uiso 1 1 calc R U . . .
C18B C 0.24030(15) 0.8975(2) 0.53825(19) 0.0698(9) Uani 1 1 d . . . . .
H18C H 0.225883 0.912325 0.488992 0.084 Uiso 1 1 calc R U . . .
H18D H 0.276919 0.859500 0.537135 0.084 Uiso 1 1 calc R U . . .
C19B C 0.19332(17) 0.8523(3) 0.5883(2) 0.0899(11) Uani 1 1 d . . . . .
H19C H 0.153004 0.862045 0.570511 0.108 Uiso 1 1 calc R U . . .
H19D H 0.200438 0.782585 0.600852 0.108 Uiso 1 1 calc R U . . .
C20B C 0.50512(12) 0.8422(2) 0.72253(15) 0.0524(7) Uani 1 1 d . . . . .
C21B C 0.57846(17) 0.7104(3) 0.7049(2) 0.0959(13) Uani 1 1 d . . . . .
H21D H 0.572038 0.639808 0.698380 0.144 Uiso 1 1 calc R U . . .
H21E H 0.588542 0.723704 0.755412 0.144 Uiso 1 1 calc R U . . .
H21F H 0.610254 0.731915 0.674346 0.144 Uiso 1 1 calc R U . . .
S1B S 0.35415(3) 1.21671(6) 0.59911(4) 0.0571(2) Uani 1 1 d . . . . .
F1B F 0.3124(3) 1.4294(6) 0.3953(5) 0.130(3) Uani 0.775(5) 1 d . U P B 1
F2B F 0.3005(2) 1.5403(4) 0.4603(3) 0.1324(18) Uani 0.775(5) 1 d . U P B 1
F12 F 0.2966(11) 1.4112(19) 0.3799(13) 0.096(5) Uani 0.225(5) 1 d . U P B 2
F22 F 0.2660(7) 1.5745(12) 0.4550(11) 0.114(4) Uani 0.225(5) 1 d . U P B 2
F3B F 0.23465(12) 1.51436(19) 0.37500(14) 0.1176(8) Uani 1 1 d . U . . .
F4B F 0.40848(11) 0.9078(2) 0.80889(11) 0.0839(10) Uani 0.775(5) 1 d . . P B 1
F42 F 0.4912(3) 0.9077(6) 0.5689(4) 0.069(3) Uani 0.225(5) 1 d . . P B 2
O1B O 0.15512(10) 1.07402(17) 0.54109(16) 0.0921(8) Uani 1 1 d . . . . .
O2B O 0.52891(10) 0.87254(18) 0.77933(11) 0.0759(6) Uani 1 1 d . . . . .
N1B N 0.15343(11) 1.3900(2) 0.56110(15) 0.0645(7) Uani 1 1 d . . . . .
N2B N 0.24191(9) 1.16031(16) 0.56400(12) 0.0482(5) Uani 1 1 d . . . . .
N3B N 0.29911(9) 1.03924(16) 0.60561(12) 0.0477(5) Uani 1 1 d . . . . .
N4B N 0.1476(2) 1.6270(3) 0.5049(2) 0.1368(16) Uani 1 1 d . . . . .
N5B N 0.52454(12) 0.7649(2) 0.68474(15) 0.0668(8) Uani 1 1 d . . . . .
H5NB H 0.5102(14) 0.749(2) 0.6464(18) 0.063(10) Uiso 1 1 d . . . . .
C22A C 0.1614(3) 0.8365(5) 0.3044(4) 0.0795(18) Uani 0.654(10) 1 d . U P C 1
C23A C 0.1745(7) 0.7381(11) 0.3413(8) 0.109(3) Uani 0.654(10) 1 d . U P C 1
H23A H 0.138051 0.703541 0.350420 0.163 Uiso 0.654(10) 1 calc R U P C 1
H23B H 0.195091 0.749912 0.387020 0.163 Uiso 0.654(10) 1 calc R U P C 1
H23C H 0.198752 0.697852 0.310082 0.163 Uiso 0.654(10) 1 calc R U P C 1
C24A C 0.0862(5) 0.7423(8) 0.2328(6) 0.100(3) Uani 0.654(10) 1 d . U P C 1
H24A H 0.045287 0.748581 0.245624 0.150 Uiso 0.654(10) 1 calc R U P C 1
H24B H 0.103920 0.688360 0.260310 0.150 Uiso 0.654(10) 1 calc R U P C 1
H24C H 0.088977 0.728486 0.181276 0.150 Uiso 0.654(10) 1 calc R U P C 1
C25A C 0.1122(6) 0.9529(9) 0.2202(9) 0.118(3) Uani 0.654(10) 1 d . U P C 1
H25A H 0.147860 0.990904 0.228229 0.177 Uiso 0.654(10) 1 calc R U P C 1
H25B H 0.079935 0.985346 0.244242 0.177 Uiso 0.654(10) 1 calc R U P C 1
H25C H 0.103742 0.948877 0.168433 0.177 Uiso 0.654(10) 1 calc R U P C 1
O3A O 0.1933(4) 0.9123(13) 0.3187(9) 0.100(2) Uani 0.654(10) 1 d . U P C 1
N6A N 0.1205(3) 0.8457(7) 0.2518(4) 0.0941(19) Uani 0.654(10) 1 d . U P C 1
C221 C 0.1415(8) 0.8862(15) 0.2738(11) 0.098(3) Uani 0.346(10) 1 d . U P C 2
C231 C 0.0959(12) 0.9253(18) 0.2151(18) 0.117(5) Uani 0.346(10) 1 d . U P C 2
H23D H 0.106307 0.900511 0.167569 0.175 Uiso 0.346(10) 1 calc R U P C 2
H23E H 0.096346 0.997315 0.214593 0.175 Uiso 0.346(10) 1 calc R U P C 2
H23F H 0.056958 0.902225 0.227081 0.175 Uiso 0.346(10) 1 calc R U P C 2
C241 C 0.0782(11) 0.7781(16) 0.2128(14) 0.111(4) Uani 0.346(10) 1 d . U P C 2
H24D H 0.047304 0.826172 0.220945 0.167 Uiso 0.346(10) 1 calc R U P C 2
H24E H 0.061969 0.711628 0.214642 0.167 Uiso 0.346(10) 1 calc R U P C 2
H24F H 0.095069 0.789444 0.165549 0.167 Uiso 0.346(10) 1 calc R U P C 2
C251 C 0.1606(13) 0.726(2) 0.3215(16) 0.100(5) Uani 0.346(10) 1 d . U P C 2
H25D H 0.200726 0.749300 0.324797 0.150 Uiso 0.346(10) 1 calc R U P C 2
H25E H 0.160158 0.658424 0.302714 0.150 Uiso 0.346(10) 1 calc R U P C 2
H25F H 0.143505 0.726488 0.369424 0.150 Uiso 0.346(10) 1 calc R U P C 2
O31 O 0.1737(9) 0.915(3) 0.3255(18) 0.106(5) Uani 0.346(10) 1 d . U P C 2
N61 N 0.1269(6) 0.7896(11) 0.2732(8) 0.091(3) Uani 0.346(10) 1 d . U P C 2
C22B C 0.0322(5) 1.1666(12) 0.6315(6) 0.111(3) Uani 0.560(13) 1 d . U P D 1
C23B C 0.0256(8) 1.0545(14) 0.6350(9) 0.129(4) Uani 0.560(13) 1 d . U P D 1
H23G H -0.015646 1.037255 0.634233 0.194 Uiso 0.560(13) 1 calc R U P D 1
H23H H 0.043830 1.029968 0.679533 0.194 Uiso 0.560(13) 1 calc R U P D 1
H23I H 0.044556 1.024588 0.593597 0.194 Uiso 0.560(13) 1 calc R U P D 1
C24B C -0.0376(8) 1.1910(15) 0.5226(10) 0.138(5) Uani 0.560(13) 1 d . U P D 1
H24G H -0.046135 1.248139 0.492199 0.206 Uiso 0.560(13) 1 calc R U P D 1
H24H H -0.073923 1.162807 0.539763 0.206 Uiso 0.560(13) 1 calc R U P D 1
H24I H -0.016752 1.141661 0.494613 0.206 Uiso 0.560(13) 1 calc R U P D 1
C25B C 0.0051(11) 1.334(2) 0.5819(9) 0.129(4) Uani 0.560(13) 1 d . U P D 1
H25G H 0.029118 1.357098 0.622422 0.194 Uiso 0.560(13) 1 calc R U P D 1
H25H H -0.033440 1.363979 0.584140 0.194 Uiso 0.560(13) 1 calc R U P D 1
H25I H 0.023406 1.352363 0.536622 0.194 Uiso 0.560(13) 1 calc R U P D 1
O3B O 0.0697(7) 1.2040(9) 0.6725(11) 0.112(3) Uani 0.560(13) 1 d . U P D 1
N6B N -0.0007(6) 1.2221(11) 0.5857(8) 0.121(3) Uani 0.560(13) 1 d . U P D 1
C222 C 0.0244(6) 1.2490(16) 0.6244(9) 0.112(3) Uani 0.440(13) 1 d . U P D 2
C232 C 0.0044(14) 1.344(3) 0.6087(12) 0.130(4) Uani 0.440(13) 1 d . U P D 2
H23J H -0.008117 1.347456 0.558106 0.195 Uiso 0.440(13) 1 calc R U P D 2
H23K H 0.035683 1.391505 0.617467 0.195 Uiso 0.440(13) 1 calc R U P D 2
H23L H -0.028479 1.359774 0.639457 0.195 Uiso 0.440(13) 1 calc R U P D 2
C242 C 0.0169(11) 1.0684(19) 0.6059(11) 0.133(4) Uani 0.440(13) 1 d . U P D 2
H24J H -0.014685 1.029700 0.626233 0.200 Uiso 0.440(13) 1 calc R U P D 2
H24K H 0.050564 1.066910 0.638731 0.200 Uiso 0.440(13) 1 calc R U P D 2
H24L H 0.027667 1.040486 0.559367 0.200 Uiso 0.440(13) 1 calc R U P D 2
C252 C -0.0486(10) 1.1564(19) 0.5444(12) 0.129(5) Uani 0.440(13) 1 d . U P D 2
H25J H -0.074779 1.104362 0.560473 0.194 Uiso 0.440(13) 1 calc R U P D 2
H25K H -0.032809 1.138690 0.497552 0.194 Uiso 0.440(13) 1 calc R U P D 2
H25L H -0.070159 1.218249 0.540036 0.194 Uiso 0.440(13) 1 calc R U P D 2
O32 O 0.0595(10) 1.2413(14) 0.6754(14) 0.126(4) Uani 0.440(13) 1 d . U P D 2
N62 N -0.0019(8) 1.1680(15) 0.5960(10) 0.124(3) Uani 0.440(13) 1 d . U P D 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
C1A C5A 1.369(4) . ?
C1A C2A 1.371(4) . ?
C1A N2A 1.427(3) . ?
C2A C3A 1.379(4) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.386(4) . ?
C3A C9A 1.489(4) . ?
C4A N1A 1.330(4) . ?
C4A C10A 1.452(5) . ?
C5A N1A 1.327(4) . ?
C5A H5A 0.9300 . ?
C6A N3A 1.339(3) . ?
C6A N2A 1.394(3) . ?
C6A S1A 1.639(3) . ?
C7A N3A 1.467(3) . ?
C7A C8A 1.502(4) . ?
C7A C17A 1.538(4) . ?
C7A C18A 1.540(4) . ?
C8A O1A 1.199(3) . ?
C8A N2A 1.384(4) . ?
C9A F11 1.178(16) . ?
C9A F3A 1.269(4) . ?
C9A F2A 1.308(5) . ?
C9A F21 1.32(2) . ?
C9A F1A 1.345(5) . ?
C9A F31 1.36(2) . ?
C10A N4A 1.133(4) . ?
C11A C16A 1.371(4) . ?
C11A C12A 1.376(4) . ?
C11A N3A 1.428(3) . ?
C12A C13A 1.372(4) . ?
C12A H12 0.9300 . ?
C13A F4A 1.330(3) . ?
C13A C14A 1.373(4) . ?
C13A H131 0.9300 . ?
C14A C15A 1.371(4) . ?
C14A C20A 1.504(4) . ?
C15A F41 1.019(17) . ?
C15A C16A 1.383(4) . ?
C15A H15A 0.9300 . ?
C16A H16 0.9300 . ?
C17A C19A 1.516(6) . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C18A C19A 1.510(5) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C20A O2A 1.230(3) . ?
C20A N5A 1.314(4) . ?
C21A N5A 1.460(4) . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
N5A H5NA 0.85(3) . ?
C1B C2B 1.374(4) . ?
C1B C5B 1.380(4) . ?
C1B N2B 1.425(3) . ?
C2B C3B 1.381(4) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.397(4) . ?
C3B C9B 1.476(5) . ?
C4B N1B 1.323(4) . ?
C4B C10B 1.444(5) . ?
C5B N1B 1.334(4) . ?
C5B H5B 0.9300 . ?
C6B N3B 1.345(3) . ?
C6B N2B 1.401(3) . ?
C6B S1B 1.635(3) . ?
C7B N3B 1.460(3) . ?
C7B C8B 1.498(4) . ?
C7B C17B 1.543(4) . ?
C7B C18B 1.544(4) . ?
C8B O1B 1.204(3) . ?
C8B N2B 1.391(3) . ?
C9B F2B 1.305(6) . ?
C9B F3B 1.308(4) . ?
C9B F1B 1.309(8) . ?
C9B F12 1.37(2) . ?
C9B F22 1.442(18) . ?
C10B N4B 1.135(4) . ?
C11B C16B 1.378(4) . ?
C11B C12B 1.379(4) . ?
C11B N3B 1.431(3) . ?
C12B C13B 1.371(4) . ?
C12B H12B 0.9300 . ?
C13B F4B 1.356(3) . ?
C13B C14B 1.379(4) . ?
C13B H132 0.9300 . ?
C14B C15B 1.390(4) . ?
C14B C20B 1.507(4) . ?
C15B C16B 1.377(4) . ?
C15B F42 1.381(8) . ?
C15B H15B 0.9300 . ?
C16B H16B 0.9300 . ?
C17B C19B 1.526(5) . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?
C18B C19B 1.534(5) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C20B O2B 1.227(3) . ?
C20B N5B 1.319(4) . ?
C21B N5B 1.460(4) . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?
N5B H5NB 0.79(3) . ?
C22A O3A 1.265(17) . ?
C22A N6A 1.326(13) . ?
C22A C23A 1.502(16) . ?
C23A H23A 0.9600 . ?
C23A H23B 0.9600 . ?
C23A H23C 0.9600 . ?
C24A N6A 1.617(14) . ?
C24A H24A 0.9600 . ?
C24A H24B 0.9600 . ?
C24A H24C 0.9600 . ?
C25A N6A 1.552(16) . ?
C25A H25A 0.9600 . ?
C25A H25B 0.9600 . ?
C25A H25C 0.9600 . ?
C221 O31 1.24(3) . ?
C221 N61 1.33(3) . ?
C221 C231 1.56(4) . ?
C231 C241 2.00(4) . ?
C231 H23D 0.9600 . ?
C231 H23E 0.9600 . ?
C231 H23F 0.9600 . ?
C241 N61 1.55(3) . ?
C241 H24D 0.9600 . ?
C241 H24E 0.9600 . ?
C241 H24F 0.9600 . ?
C251 N61 1.44(3) . ?
C251 H25D 0.9600 . ?
C251 H25E 0.9600 . ?
C251 H25F 0.9600 . ?
C22B O3B 1.226(17) . ?
C22B N6B 1.33(2) . ?
C22B C23B 1.50(2) . ?
C23B H23G 0.9600 . ?
C23B H23H 0.9600 . ?
C23B H23I 0.9600 . ?
C24B N6B 1.468(19) . ?
C24B H24G 0.9600 . ?
C24B H24H 0.9600 . ?
C24B H24I 0.9600 . ?
C25B N6B 1.50(3) . ?
C25B H25G 0.9600 . ?
C25B H25H 0.9600 . ?
C25B H25I 0.9600 . ?
C222 O32 1.21(2) . ?
C222 N62 1.33(3) . ?
C222 C232 1.38(4) . ?
C232 H23J 0.9600 . ?
C232 H23K 0.9600 . ?
C232 H23L 0.9600 . ?
C242 N62 1.40(3) . ?
C242 H24J 0.9600 . ?
C242 H24K 0.9600 . ?
C242 H24L 0.9600 . ?
C252 N62 1.41(2) . ?
C252 H25J 0.9600 . ?
C252 H25K 0.9600 . ?
C252 H25L 0.9600 . ?

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
C5A C1A C2A 119.0(3) . . ?
C5A C1A N2A 119.4(3) . . ?
C2A C1A N2A 121.5(3) . . ?
C1A C2A C3A 118.7(3) . . ?
C1A C2A H2A 120.6 . . ?
C3A C2A H2A 120.6 . . ?
C2A C3A C4A 117.9(3) . . ?
C2A C3A C9A 120.5(3) . . ?
C4A C3A C9A 121.5(3) . . ?
N1A C4A C3A 123.8(3) . . ?
N1A C4A C10A 114.5(3) . . ?
C3A C4A C10A 121.7(3) . . ?
N1A C5A C1A 123.8(3) . . ?
N1A C5A H5A 118.1 . . ?
C1A C5A H5A 118.1 . . ?
N3A C6A N2A 106.9(2) . . ?
N3A C6A S1A 127.7(2) . . ?
N2A C6A S1A 125.3(2) . . ?
N3A C7A C8A 101.0(2) . . ?
N3A C7A C17A 119.9(3) . . ?
C8A C7A C17A 115.1(3) . . ?
N3A C7A C18A 119.9(2) . . ?
C8A C7A C18A 114.0(3) . . ?
C17A C7A C18A 87.8(3) . . ?
O1A C8A N2A 125.4(3) . . ?
O1A C8A C7A 127.3(3) . . ?
N2A C8A C7A 107.3(2) . . ?
F3A C9A F2A 108.1(4) . . ?
F11 C9A F21 114.1(16) . . ?
F3A C9A F1A 104.5(4) . . ?
F2A C9A F1A 102.7(4) . . ?
F11 C9A F31 108.4(16) . . ?
F21 C9A F31 105.8(14) . . ?
F11 C9A C3A 109.5(9) . . ?
F3A C9A C3A 115.3(3) . . ?
F2A C9A C3A 113.2(3) . . ?
F21 C9A C3A 114.3(10) . . ?
F1A C9A C3A 111.9(3) . . ?
F31 C9A C3A 104.1(9) . . ?
N4A C10A C4A 177.2(5) . . ?
C16A C11A C12A 120.6(2) . . ?
C16A C11A N3A 120.7(3) . . ?
C12A C11A N3A 118.6(2) . . ?
C13A C12A C11A 118.2(3) . . ?
C13A C12A H12 120.9 . . ?
C11A C12A H12 120.9 . . ?
F4A C13A C12A 118.1(3) . . ?
F4A C13A C14A 118.6(3) . . ?
C12A C13A C14A 123.3(3) . . ?
C12A C13A H131 118.3 . . ?
C14A C13A H131 118.3 . . ?
C15A C14A C13A 116.7(2) . . ?
C15A C14A C20A 122.9(3) . . ?
C13A C14A C20A 120.4(3) . . ?
F41 C15A C14A 119.2(9) . . ?
F41 C15A C16A 118.0(10) . . ?
C14A C15A C16A 122.0(3) . . ?
C14A C15A H15A 119.0 . . ?
C16A C15A H15A 119.0 . . ?
C11A C16A C15A 119.1(3) . . ?
C11A C16A H16 120.4 . . ?
C15A C16A H16 120.4 . . ?
C19A C17A C7A 89.1(3) . . ?
C19A C17A H17A 113.8 . . ?
C7A C17A H17A 113.8 . . ?
C19A C17A H17B 113.8 . . ?
C7A C17A H17B 113.8 . . ?
H17A C17A H17B 111.0 . . ?
C19A C18A C7A 89.2(3) . . ?
C19A C18A H18A 113.8 . . ?
C7A C18A H18A 113.8 . . ?
C19A C18A H18B 113.8 . . ?
C7A C18A H18B 113.8 . . ?
H18A C18A H18B 111.0 . . ?
C18A C19A C17A 89.7(3) . . ?
C18A C19A H19A 113.7 . . ?
C17A C19A H19A 113.7 . . ?
C18A C19A H19B 113.7 . . ?
C17A C19A H19B 113.7 . . ?
H19A C19A H19B 110.9 . . ?
O2A C20A N5A 123.5(3) . . ?
O2A C20A C14A 120.6(3) . . ?
N5A C20A C14A 116.0(2) . . ?
N5A C21A H21A 109.5 . . ?
N5A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
N5A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C5A N1A C4A 116.8(3) . . ?
C8A N2A C6A 111.4(2) . . ?
C8A N2A C1A 123.1(2) . . ?
C6A N2A C1A 124.8(2) . . ?
C6A N3A C11A 123.5(2) . . ?
C6A N3A C7A 113.3(2) . . ?
C11A N3A C7A 122.9(2) . . ?
C20A N5A C21A 122.1(3) . . ?
C20A N5A H5NA 120(2) . . ?
C21A N5A H5NA 118(2) . . ?
C2B C1B C5B 120.1(3) . . ?
C2B C1B N2B 120.9(2) . . ?
C5B C1B N2B 119.0(3) . . ?
C1B C2B C3B 118.5(3) . . ?
C1B C2B H2B 120.7 . . ?
C3B C2B H2B 120.7 . . ?
C2B C3B C4B 117.2(3) . . ?
C2B C3B C9B 120.2(3) . . ?
C4B C3B C9B 122.6(3) . . ?
N1B C4B C3B 124.4(3) . . ?
N1B C4B C10B 113.6(3) . . ?
C3B C4B C10B 121.9(3) . . ?
N1B C5B C1B 122.2(3) . . ?
N1B C5B H5B 118.9 . . ?
C1B C5B H5B 118.9 . . ?
N3B C6B N2B 106.1(2) . . ?
N3B C6B S1B 127.60(19) . . ?
N2B C6B S1B 126.2(2) . . ?
N3B C7B C8B 101.3(2) . . ?
N3B C7B C17B 120.7(2) . . ?
C8B C7B C17B 113.7(2) . . ?
N3B C7B C18B 120.3(2) . . ?
C8B C7B C18B 113.2(2) . . ?
C17B C7B C18B 88.3(2) . . ?
O1B C8B N2B 125.1(3) . . ?
O1B C8B C7B 127.8(3) . . ?
N2B C8B C7B 107.1(2) . . ?
F2B C9B F3B 111.5(4) . . ?
F2B C9B F1B 94.3(6) . . ?
F3B C9B F1B 107.9(5) . . ?
F3B C9B F12 94.4(12) . . ?
F3B C9B F22 81.6(8) . . ?
F12 C9B F22 143.8(13) . . ?
F2B C9B C3B 112.7(4) . . ?
F3B C9B C3B 113.9(3) . . ?
F1B C9B C3B 115.0(4) . . ?
F12 C9B C3B 107.4(12) . . ?
F22 C9B C3B 107.0(8) . . ?
N4B C10B C4B 177.4(4) . . ?
C16B C11B C12B 120.4(2) . . ?
C16B C11B N3B 119.9(2) . . ?
C12B C11B N3B 119.8(2) . . ?
C13B C12B C11B 118.7(3) . . ?
C13B C12B H12B 120.6 . . ?
C11B C12B H12B 120.6 . . ?
F4B C13B C12B 116.7(3) . . ?
F4B C13B C14B 120.3(2) . . ?
C12B C13B C14B 123.0(2) . . ?
C12B C13B H132 118.5 . . ?
C14B C13B H132 118.5 . . ?
C13B C14B C15B 116.7(2) . . ?
C13B C14B C20B 121.4(2) . . ?
C15B C14B C20B 121.9(2) . . ?
C16B C15B F42 114.3(4) . . ?
C16B C15B C14B 121.7(3) . . ?
F42 C15B C14B 122.5(4) . . ?
C16B C15B H15B 119.1 . . ?
C14B C15B H15B 119.1 . . ?
C15B C16B C11B 119.5(2) . . ?
C15B C16B H16B 120.3 . . ?
C11B C16B H16B 120.3 . . ?
C19B C17B C7B 88.7(3) . . ?
C19B C17B H17C 113.9 . . ?
C7B C17B H17C 113.9 . . ?
C19B C17B H17D 113.9 . . ?
C7B C17B H17D 113.9 . . ?
H17C C17B H17D 111.1 . . ?
C19B C18B C7B 88.3(3) . . ?
C19B C18B H18C 113.9 . . ?
C7B C18B H18C 113.9 . . ?
C19B C18B H18D 113.9 . . ?
C7B C18B H18D 113.9 . . ?
H18C C18B H18D 111.1 . . ?
C17B C19B C18B 89.3(2) . . ?
C17B C19B H19C 113.8 . . ?
C18B C19B H19C 113.8 . . ?
C17B C19B H19D 113.8 . . ?
C18B C19B H19D 113.8 . . ?
H19C C19B H19D 111.0 . . ?
O2B C20B N5B 123.6(3) . . ?
O2B C20B C14B 121.0(3) . . ?
N5B C20B C14B 115.4(2) . . ?
N5B C21B H21D 109.5 . . ?
N5B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
N5B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C4B N1B C5B 117.3(3) . . ?
C8B N2B C6B 111.6(2) . . ?
C8B N2B C1B 124.1(2) . . ?
C6B N2B C1B 124.2(2) . . ?
C6B N3B C11B 122.1(2) . . ?
C6B N3B C7B 113.8(2) . . ?
C11B N3B C7B 124.1(2) . . ?
C20B N5B C21B 122.7(3) . . ?
C20B N5B H5NB 122(2) . . ?
C21B N5B H5NB 114(2) . . ?
O3A C22A N6A 117.5(11) . . ?
O3A C22A C23A 119.9(10) . . ?
N6A C22A C23A 122.3(9) . . ?
C22A C23A H23A 109.5 . . ?
C22A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C22A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
N6A C24A H24A 109.5 . . ?
N6A C24A H24B 109.5 . . ?
H24A C24A H24B 109.5 . . ?
N6A C24A H24C 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
N6A C25A H25A 109.5 . . ?
N6A C25A H25B 109.5 . . ?
H25A C25A H25B 109.5 . . ?
N6A C25A H25C 109.5 . . ?
H25A C25A H25C 109.5 . . ?
H25B C25A H25C 109.5 . . ?
C22A N6A C25A 115.6(8) . . ?
C22A N6A C24A 113.6(9) . . ?
C25A N6A C24A 130.7(9) . . ?
O31 C221 N61 117(3) . . ?
O31 C221 C231 142(3) . . ?
N61 C221 C231 99.0(18) . . ?
C221 C231 C241 79.4(15) . . ?
C221 C231 H23D 109.5 . . ?
C241 C231 H23D 72.3 . . ?
C221 C231 H23E 109.5 . . ?
C241 C231 H23E 169.0 . . ?
H23D C231 H23E 109.5 . . ?
C221 C231 H23F 109.5 . . ?
C241 C231 H23F 60.5 . . ?
H23D C231 H23F 109.5 . . ?
H23E C231 H23F 109.5 . . ?
N61 C241 C231 75.5(13) . . ?
N61 C241 H24D 109.5 . . ?
C231 C241 H24D 59.2 . . ?
N61 C241 H24E 109.5 . . ?
C231 C241 H24E 168.6 . . ?
H24D C241 H24E 109.5 . . ?
N61 C241 H24F 109.5 . . ?
C231 C241 H24F 77.4 . . ?
H24D C241 H24F 109.5 . . ?
H24E C241 H24F 109.5 . . ?
N61 C251 H25D 109.5 . . ?
N61 C251 H25E 109.5 . . ?
H25D C251 H25E 109.5 . . ?
N61 C251 H25F 109.5 . . ?
H25D C251 H25F 109.5 . . ?
H25E C251 H25F 109.5 . . ?
C221 N61 C251 116.2(18) . . ?
C221 N61 C241 106(2) . . ?
C251 N61 C241 137.7(17) . . ?
O3B C22B N6B 121.8(16) . . ?
O3B C22B C23B 116.5(12) . . ?
N6B C22B C23B 121.7(14) . . ?
C22B C23B H23G 109.5 . . ?
C22B C23B H23H 109.5 . . ?
H23G C23B H23H 109.5 . . ?
C22B C23B H23I 109.5 . . ?
H23G C23B H23I 109.5 . . ?
H23H C23B H23I 109.5 . . ?
N6B C24B H24G 109.5 . . ?
N6B C24B H24H 109.5 . . ?
H24G C24B H24H 109.5 . . ?
N6B C24B H24I 109.5 . . ?
H24G C24B H24I 109.5 . . ?
H24H C24B H24I 109.5 . . ?
N6B C25B H25G 109.5 . . ?
N6B C25B H25H 109.5 . . ?
H25G C25B H25H 109.5 . . ?
N6B C25B H25I 109.5 . . ?
H25G C25B H25I 109.5 . . ?
H25H C25B H25I 109.5 . . ?
C22B N6B C24B 129.5(15) . . ?
C22B N6B C25B 122.3(16) . . ?
C24B N6B C25B 107.1(13) . . ?
O32 C222 N62 121(2) . . ?
O32 C222 C232 116(2) . . ?
N62 C222 C232 122(2) . . ?
C222 C232 H23J 109.5 . . ?
C222 C232 H23K 109.5 . . ?
H23J C232 H23K 109.5 . . ?
C222 C232 H23L 109.5 . . ?
H23J C232 H23L 109.5 . . ?
H23K C232 H23L 109.5 . . ?
N62 C242 H24J 109.5 . . ?
N62 C242 H24K 109.5 . . ?
H24J C242 H24K 109.5 . . ?
N62 C242 H24L 109.5 . . ?
H24J C242 H24L 109.5 . . ?
H24K C242 H24L 109.5 . . ?
N62 C252 H25J 109.5 . . ?
N62 C252 H25K 109.5 . . ?
H25J C252 H25K 109.5 . . ?
N62 C252 H25L 109.5 . . ?
H25J C252 H25L 109.5 . . ?
H25K C252 H25L 109.5 . . ?
C222 N62 C242 126(2) . . ?
C222 N62 C252 132(2) . . ?
C242 N62 C252 101.7(17) . . ?

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
C5A C1A C2A C3A -0.2(4) . . . . ?
N2A C1A C2A C3A -177.3(2) . . . . ?
C1A C2A C3A C4A -0.2(4) . . . . ?
C1A C2A C3A C9A 179.1(3) . . . . ?
C2A C3A C4A N1A 0.6(5) . . . . ?
C9A C3A C4A N1A -178.7(3) . . . . ?
C2A C3A C4A C10A -176.8(3) . . . . ?
C9A C3A C4A C10A 3.9(5) . . . . ?
C2A C1A C5A N1A 0.3(5) . . . . ?
N2A C1A C5A N1A 177.5(3) . . . . ?
N3A C7A C8A O1A 178.5(3) . . . . ?
C17A C7A C8A O1A 47.8(5) . . . . ?
C18A C7A C8A O1A -51.6(5) . . . . ?
N3A C7A C8A N2A 0.0(3) . . . . ?
C17A C7A C8A N2A -130.7(3) . . . . ?
C18A C7A C8A N2A 130.0(3) . . . . ?
C2A C3A C9A F11 47.2(16) . . . . ?
C4A C3A C9A F11 -133.6(16) . . . . ?
C2A C3A C9A F3A -122.3(5) . . . . ?
C4A C3A C9A F3A 56.9(6) . . . . ?
C2A C3A C9A F2A 112.5(4) . . . . ?
C4A C3A C9A F2A -68.2(5) . . . . ?
C2A C3A C9A F21 176.5(14) . . . . ?
C4A C3A C9A F21 -4.2(15) . . . . ?
C2A C3A C9A F1A -3.0(5) . . . . ?
C4A C3A C9A F1A 176.2(4) . . . . ?
C2A C3A C9A F31 -68.6(12) . . . . ?
C4A C3A C9A F31 110.7(12) . . . . ?
C16A C11A C12A C13A 1.1(4) . . . . ?
N3A C11A C12A C13A 179.6(2) . . . . ?
C11A C12A C13A F4A 179.2(3) . . . . ?
C11A C12A C13A C14A -2.0(4) . . . . ?
F4A C13A C14A C15A 180.0(3) . . . . ?
C12A C13A C14A C15A 1.2(4) . . . . ?
F4A C13A C14A C20A -2.1(4) . . . . ?
C12A C13A C14A C20A 179.1(3) . . . . ?
C13A C14A C15A F41 169.7(14) . . . . ?
C20A C14A C15A F41 -8.2(15) . . . . ?
C13A C14A C15A C16A 0.5(4) . . . . ?
C20A C14A C15A C16A -177.4(3) . . . . ?
C12A C11A C16A C15A 0.4(4) . . . . ?
N3A C11A C16A C15A -178.0(3) . . . . ?
F41 C15A C16A C11A -170.6(14) . . . . ?
C14A C15A C16A C11A -1.2(5) . . . . ?
N3A C7A C17A C19A 138.8(3) . . . . ?
C8A C7A C17A C19A -100.3(3) . . . . ?
C18A C7A C17A C19A 15.3(3) . . . . ?
N3A C7A C18A C19A -138.9(3) . . . . ?
C8A C7A C18A C19A 101.3(3) . . . . ?
C17A C7A C18A C19A -15.3(3) . . . . ?
C7A C18A C19A C17A 15.6(3) . . . . ?
C7A C17A C19A C18A -15.6(3) . . . . ?
C15A C14A C20A O2A 123.4(4) . . . . ?
C13A C14A C20A O2A -54.4(4) . . . . ?
C15A C14A C20A N5A -57.4(4) . . . . ?
C13A C14A C20A N5A 124.8(3) . . . . ?
C1A C5A N1A C4A 0.1(5) . . . . ?
C3A C4A N1A C5A -0.5(5) . . . . ?
C10A C4A N1A C5A 177.1(3) . . . . ?
O1A C8A N2A C6A -179.7(3) . . . . ?
C7A C8A N2A C6A -1.2(3) . . . . ?
O1A C8A N2A C1A 8.8(5) . . . . ?
C7A C8A N2A C1A -172.7(3) . . . . ?
N3A C6A N2A C8A 2.1(3) . . . . ?
S1A C6A N2A C8A 179.2(2) . . . . ?
N3A C6A N2A C1A 173.4(2) . . . . ?
S1A C6A N2A C1A -9.5(4) . . . . ?
C5A C1A N2A C8A -75.8(4) . . . . ?
C2A C1A N2A C8A 101.3(3) . . . . ?
C5A C1A N2A C6A 113.8(3) . . . . ?
C2A C1A N2A C6A -69.0(4) . . . . ?
N2A C6A N3A C11A -176.0(2) . . . . ?
S1A C6A N3A C11A 6.9(4) . . . . ?
N2A C6A N3A C7A -2.1(3) . . . . ?
S1A C6A N3A C7A -179.1(2) . . . . ?
C16A C11A N3A C6A -102.8(3) . . . . ?
C12A C11A N3A C6A 78.8(4) . . . . ?
C16A C11A N3A C7A 83.9(4) . . . . ?
C12A C11A N3A C7A -94.6(3) . . . . ?
C8A C7A N3A C6A 1.3(3) . . . . ?
C17A C7A N3A C6A 128.9(3) . . . . ?
C18A C7A N3A C6A -124.9(3) . . . . ?
C8A C7A N3A C11A 175.3(3) . . . . ?
C17A C7A N3A C11A -57.1(4) . . . . ?
C18A C7A N3A C11A 49.1(4) . . . . ?
O2A C20A N5A C21A -4.8(5) . . . . ?
C14A C20A N5A C21A 175.9(3) . . . . ?
C5B C1B C2B C3B 3.2(4) . . . . ?
N2B C1B C2B C3B -176.4(2) . . . . ?
C1B C2B C3B C4B -0.7(4) . . . . ?
C1B C2B C3B C9B 177.1(3) . . . . ?
C2B C3B C4B N1B -2.8(4) . . . . ?
C9B C3B C4B N1B 179.4(3) . . . . ?
C2B C3B C4B C10B 175.5(3) . . . . ?
C9B C3B C4B C10B -2.3(4) . . . . ?
C2B C1B C5B N1B -2.5(4) . . . . ?
N2B C1B C5B N1B 177.1(2) . . . . ?
N3B C7B C8B O1B 179.4(3) . . . . ?
C17B C7B C8B O1B -49.6(5) . . . . ?
C18B C7B C8B O1B 49.2(5) . . . . ?
N3B C7B C8B N2B 0.7(3) . . . . ?
C17B C7B C8B N2B 131.7(3) . . . . ?
C18B C7B C8B N2B -129.5(3) . . . . ?
C2B C3B C9B F2B -103.0(5) . . . . ?
C4B C3B C9B F2B 74.7(5) . . . . ?
C2B C3B C9B F3B 128.7(3) . . . . ?
C4B C3B C9B F3B -53.6(5) . . . . ?
C2B C3B C9B F1B 3.4(6) . . . . ?
C4B C3B C9B F1B -178.9(5) . . . . ?
C2B C3B C9B F12 25.5(12) . . . . ?
C4B C3B C9B F12 -156.7(12) . . . . ?
C2B C3B C9B F22 -143.2(8) . . . . ?
C4B C3B C9B F22 34.5(8) . . . . ?
C16B C11B C12B C13B -0.9(4) . . . . ?
N3B C11B C12B C13B -179.8(2) . . . . ?
C11B C12B C13B F4B -180.0(3) . . . . ?
C11B C12B C13B C14B 0.6(4) . . . . ?
F4B C13B C14B C15B -179.3(3) . . . . ?
C12B C13B C14B C15B 0.1(4) . . . . ?
F4B C13B C14B C20B -0.6(4) . . . . ?
C12B C13B C14B C20B 178.8(3) . . . . ?
C13B C14B C15B C16B -0.4(4) . . . . ?
C20B C14B C15B C16B -179.2(3) . . . . ?
C13B C14B C15B F42 164.7(5) . . . . ?
C20B C14B C15B F42 -14.1(6) . . . . ?
F42 C15B C16B C11B -166.2(4) . . . . ?
C14B C15B C16B C11B 0.1(4) . . . . ?
C12B C11B C16B C15B 0.6(4) . . . . ?
N3B C11B C16B C15B 179.5(2) . . . . ?
N3B C7B C17B C19B -142.1(3) . . . . ?
C8B C7B C17B C19B 97.3(3) . . . . ?
C18B C7B C17B C19B -17.4(3) . . . . ?
N3B C7B C18B C19B 142.3(3) . . . . ?
C8B C7B C18B C19B -97.8(3) . . . . ?
C17B C7B C18B C19B 17.3(3) . . . . ?
C7B C17B C19B C18B 17.5(3) . . . . ?
C7B C18B C19B C17B -17.5(3) . . . . ?
C13B C14B C20B O2B -42.4(4) . . . . ?
C15B C14B C20B O2B 136.3(3) . . . . ?
C13B C14B C20B N5B 137.9(3) . . . . ?
C15B C14B C20B N5B -43.4(4) . . . . ?
C3B C4B N1B C5B 3.6(4) . . . . ?
C10B C4B N1B C5B -174.9(3) . . . . ?
C1B C5B N1B C4B -0.9(4) . . . . ?
O1B C8B N2B C6B -178.3(3) . . . . ?
C7B C8B N2B C6B 0.4(3) . . . . ?
O1B C8B N2B C1B 2.5(5) . . . . ?
C7B C8B N2B C1B -178.7(2) . . . . ?
N3B C6B N2B C8B -1.5(3) . . . . ?
S1B C6B N2B C8B 179.7(2) . . . . ?
N3B C6B N2B C1B 177.6(2) . . . . ?
S1B C6B N2B C1B -1.1(4) . . . . ?
C2B C1B N2B C8B -127.4(3) . . . . ?
C5B C1B N2B C8B 53.0(4) . . . . ?
C2B C1B N2B C6B 53.6(4) . . . . ?
C5B C1B N2B C6B -126.0(3) . . . . ?
N2B C6B N3B C11B -179.0(2) . . . . ?
S1B C6B N3B C11B -0.3(4) . . . . ?
N2B C6B N3B C7B 2.0(3) . . . . ?
S1B C6B N3B C7B -179.2(2) . . . . ?
C16B C11B N3B C6B -79.8(3) . . . . ?
C12B C11B N3B C6B 99.1(3) . . . . ?
C16B C11B N3B C7B 99.1(3) . . . . ?
C12B C11B N3B C7B -82.1(3) . . . . ?
C8B C7B N3B C6B -1.7(3) . . . . ?
C17B C7B N3B C6B -128.2(3) . . . . ?
C18B C7B N3B C6B 123.9(3) . . . . ?
C8B C7B N3B C11B 179.4(2) . . . . ?
C17B C7B N3B C11B 52.9(4) . . . . ?
C18B C7B N3B C11B -55.0(4) . . . . ?
O2B C20B N5B C21B -3.2(5) . . . . ?
C14B C20B N5B C21B 176.6(3) . . . . ?
O3A C22A N6A C25A -6.8(13) . . . . ?
C23A C22A N6A C25A 179.4(12) . . . . ?
O3A C22A N6A C24A 174.9(10) . . . . ?
C23A C22A N6A C24A 1.0(13) . . . . ?
O31 C221 C231 C241 -162(3) . . . . ?
N61 C221 C231 C241 -2.6(16) . . . . ?
O31 C221 N61 C251 -14(3) . . . . ?
C231 C221 N61 C251 179(2) . . . . ?
O31 C221 N61 C241 170(2) . . . . ?
C231 C221 N61 C241 3(2) . . . . ?
C231 C241 N61 C221 -2.7(17) . . . . ?
C231 C241 N61 C251 -177(3) . . . . ?
O3B C22B N6B C24B 165.3(15) . . . . ?
C23B C22B N6B C24B -14.1(19) . . . . ?
O3B C22B N6B C25B -1(2) . . . . ?
C23B C22B N6B C25B 179.6(14) . . . . ?
O32 C222 N62 C242 -17(3) . . . . ?
C232 C222 N62 C242 177(2) . . . . ?
O32 C222 N62 C252 171(2) . . . . ?
C232 C222 N62 C252 5(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
_geom_hbond_publ_flag
N5A H5NA O2B 0.85(3) 2.12(3) 2.974(3) 177(3) 4_575 yes
N5B H5NB O2A 0.79(3) 2.06(3) 2.847(4) 171(3) . yes
C2A H2A O3A 0.93 2.46 3.158(17) 132 . yes
C5A H5A S1B 0.93 2.81 3.697(3) 159 4_585 yes
C5B H5B O3B 0.93 2.32 3.197(19) 157 . yes
C23B H23H N4A 0.96 2.52 3.448(15) 162 4_586 yes

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2151553'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H16 F4 N5 O2 S, C3 H7 N O'
_chemical_formula_sum            'C24 H23 F4 N6 O3 S'
_chemical_formula_weight         551.54

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   17.3059(19)
_cell_length_b                   12.2220(13)
_cell_length_c                   47.409(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10027.6(19)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9926
_cell_measurement_theta_min      2.214
_cell_measurement_theta_max      24.189

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             4560
_exptl_transmission_factor_min   0.6760
_exptl_transmission_factor_max   0.8620
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            62354
_diffrn_reflns_av_unetI/netI     0.0884
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_theta_min         1.875
_diffrn_reflns_theta_max         26.000
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             19646
_reflns_number_gt                14434
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.972
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+20.3391P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00077(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.25(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         19646
_refine_ls_number_parameters     1433
_refine_ls_number_restraints     67
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0698
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1421
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.075
_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 0.62686(12) 0.63096(17) 0.41261(5) 0.0275(5) Uani 1 1 d . . . . .
F1A F 0.6630(7) 0.9117(9) 0.5121(2) 0.039(4) Uani 0.464(12) 1 d . . P A 1
F1B F 0.5573(5) 1.0847(7) 0.43450(19) 0.030(3) Uani 0.536(12) 1 d . . P A 2
F11A F 0.7212(13) 0.6755(9) 0.2824(3) 0.053(6) Uiso 0.38(3) 1 d D . P B 9
F12A F 0.6231(7) 0.564(2) 0.2786(5) 0.075(7) Uiso 0.38(3) 1 d D . P B 9
F13A F 0.7398(9) 0.5058(15) 0.2711(4) 0.058(7) Uiso 0.38(3) 1 d D . P B 9
F11B F 0.6797(8) 0.6750(7) 0.2863(2) 0.056(4) Uiso 0.62(3) 1 d D . P B 10
F12B F 0.6227(5) 0.5178(10) 0.2852(2) 0.049(3) Uiso 0.62(3) 1 d D . P B 10
F13B F 0.7421(6) 0.5338(11) 0.2686(2) 0.050(4) Uiso 0.62(3) 1 d D . P B 10
O11 O 0.4782(3) 1.0642(5) 0.48611(14) 0.0354(15) Uani 1 1 d . . . . .
O12 O 0.8740(3) 0.7526(5) 0.36819(13) 0.0275(14) Uani 1 1 d . . . . .
N11 N 0.5798(4) 1.1070(6) 0.51420(15) 0.0247(16) Uani 1 1 d . . . . .
H1 H 0.629(5) 1.108(7) 0.5151(19) 0.030 Uiso 1 1 d . U . . .
N12 N 0.7342(4) 0.7890(5) 0.42060(14) 0.0215(15) Uani 1 1 d . U . . .
N13 N 0.7633(4) 0.6726(5) 0.38659(14) 0.0197(14) Uani 1 1 d . . . . .
N14 N 0.7396(5) 0.4012(6) 0.35405(17) 0.038(2) Uani 1 1 d . . . . .
N15 N 0.6851(5) 0.2757(8) 0.2929(2) 0.060(3) Uani 1 1 d . . . . .
C1 C 0.5337(5) 1.1711(7) 0.53393(19) 0.032(2) Uani 1 1 d . . . . .
H1A H 0.562765 1.236248 0.539656 0.048 Uiso 1 1 calc R U . . .
H1B H 0.521928 1.126701 0.550595 0.048 Uiso 1 1 calc R U . . .
H1C H 0.485400 1.193506 0.524806 0.048 Uiso 1 1 calc R U . . .
C10 C 0.5475(5) 1.0572(6) 0.49216(17) 0.0222(18) Uani 1 1 d . . . . .
C11 C 0.6006(5) 0.9903(6) 0.47370(17) 0.0219(18) Uani 1 1 d . . . . .
C12 C 0.6513(5) 0.9141(7) 0.48484(18) 0.030(2) Uani 1 1 d . . . . .
H12A H 0.656762 0.908882 0.504731 0.036 Uiso 1 1 calc R U . A 2
C13 C 0.6943(6) 0.8454(7) 0.46781(17) 0.029(2) Uani 1 1 d . U . . .
H13A H 0.728656 0.793041 0.475733 0.035 Uiso 1 1 calc R U . . .
C14 C 0.6860(5) 0.8550(6) 0.43907(18) 0.0215(17) Uani 1 1 d . U . . .
C15 C 0.6385(5) 0.9306(7) 0.42706(18) 0.0255(19) Uani 1 1 d . U . . .
H15A H 0.634611 0.937392 0.407151 0.031 Uiso 1 1 calc R U . . .
C16 C 0.5963(5) 0.9965(7) 0.44470(18) 0.028(2) Uani 1 1 d . . . . .
H16A H 0.562613 1.049010 0.436543 0.034 Uiso 1 1 calc R U . A 1
C17 C 0.8075(5) 0.8289(6) 0.40956(17) 0.0201(17) Uani 1 1 d . . . . .
C18 C 0.8192(5) 0.9505(7) 0.40196(18) 0.0258(19) Uani 1 1 d . . . . .
H18A H 0.783612 1.000625 0.411954 0.031 Uiso 1 1 calc R U . . .
H18B H 0.819082 0.965024 0.381419 0.031 Uiso 1 1 calc R U . . .
C19 C 0.9010(5) 0.9457(6) 0.41498(19) 0.0267(19) Uani 1 1 d . . . . .
H19A H 0.912170 1.006325 0.428217 0.032 Uiso 1 1 calc R U . . .
H19B H 0.942821 0.937499 0.400907 0.032 Uiso 1 1 calc R U . . .
C20 C 0.8778(5) 0.8363(7) 0.42984(19) 0.027(2) Uani 1 1 d . . . . .
H20A H 0.915875 0.776651 0.427361 0.033 Uiso 1 1 calc R U . . .
H20B H 0.863447 0.845040 0.449929 0.033 Uiso 1 1 calc R U . . .
C21 C 0.7086(5) 0.7004(6) 0.40690(17) 0.0201(17) Uani 1 1 d . . . . .
C22 C 0.8219(5) 0.7506(6) 0.38529(18) 0.0235(18) Uani 1 1 d . . . . .
C23 C 0.7538(5) 0.4813(7) 0.37249(19) 0.0275(19) Uani 1 1 d . . . . .
H23A H 0.766928 0.461764 0.391281 0.033 Uiso 1 1 calc R U . . .
C24 C 0.7503(5) 0.5918(7) 0.36564(17) 0.0243(18) Uani 1 1 d . . . . .
C25 C 0.7335(6) 0.6220(8) 0.3382(2) 0.040(2) Uani 1 1 d . . . . .
H25A H 0.731373 0.696940 0.332936 0.048 Uiso 1 1 calc R U . . .
C26 C 0.7196(6) 0.5394(8) 0.3184(2) 0.039(2) Uani 1 1 d . . . . .
C27 C 0.7231(5) 0.4321(8) 0.3275(2) 0.034(2) Uani 1 1 d . . . . .
C28 C 0.6948(5) 0.5687(6) 0.2889(2) 0.068(4) Uani 1 1 d D . . . .
C29 C 0.7047(5) 0.3423(9) 0.3081(2) 0.044(3) Uani 1 1 d . . . . .
S2 S 0.45871(12) 0.86751(16) 0.58807(5) 0.0251(5) Uani 1 1 d . . . . .
F2A F 0.4247(9) 0.5873(9) 0.4888(2) 0.034(4) Uani 0.397(12) 1 d . . P C 3
F2B F 0.5338(5) 0.4171(7) 0.56624(18) 0.041(3) Uani 0.603(12) 1 d . . P C 4
F21 F 0.3865(3) 1.0067(4) 0.72845(10) 0.0444(14) Uani 1 1 d . . . . .
F22 F 0.3961(4) 0.8409(4) 0.71492(11) 0.0483(15) Uani 1 1 d . . . . .
F23 F 0.2839(3) 0.9097(5) 0.72361(11) 0.0465(14) Uani 1 1 d . . . . .
O21 O 0.6090(3) 0.4372(5) 0.51408(14) 0.0354(16) Uani 1 1 d . . . . .
O22 O 0.2120(3) 0.7428(4) 0.63223(12) 0.0248(13) Uani 1 1 d . . . . .
N21 N 0.5077(4) 0.3900(6) 0.48669(15) 0.0253(16) Uani 1 1 d . . . . .
H2 H 0.464(6) 0.386(8) 0.486(2) 0.030 Uiso 1 1 d . U . . .
N22 N 0.3535(4) 0.7078(5) 0.58043(14) 0.0206(15) Uani 1 1 d . . . . .
N23 N 0.3221(4) 0.8227(5) 0.61376(14) 0.0202(14) Uani 1 1 d . . . . .
N24 N 0.3452(4) 1.0986(5) 0.64447(15) 0.0221(15) Uani 1 1 d . . . . .
N25 N 0.3741(5) 1.2448(6) 0.70325(17) 0.0384(19) Uani 1 1 d . . . . .
C2 C 0.5542(5) 0.3267(7) 0.46674(18) 0.030(2) Uani 1 1 d . . . . .
H2A H 0.521824 0.270906 0.457783 0.045 Uiso 1 1 calc R U . . .
H2B H 0.596852 0.291167 0.476811 0.045 Uiso 1 1 calc R U . . .
H2C H 0.575205 0.375660 0.452264 0.045 Uiso 1 1 calc R U . . .
C30 C 0.5396(5) 0.4409(6) 0.50843(19) 0.0243(19) Uani 1 1 d . . . . .
C31 C 0.4869(4) 0.5092(6) 0.52658(17) 0.0194(17) Uani 1 1 d . . . . .
C32 C 0.4909(5) 0.5006(6) 0.55552(18) 0.0242(18) Uani 1 1 d . . . . .
H32A H 0.524328 0.446974 0.563379 0.029 Uiso 1 1 calc R U . C 3
C33 C 0.4492(4) 0.5655(6) 0.57357(18) 0.0217(18) Uani 1 1 d . . . . .
H33A H 0.454333 0.557987 0.593431 0.026 Uiso 1 1 calc R U . . .
C34 C 0.3987(5) 0.6434(6) 0.56193(17) 0.0208(17) Uani 1 1 d . . . . .
C35 C 0.3916(5) 0.6531(7) 0.53299(18) 0.0244(18) Uani 1 1 d . . . . .
H35A H 0.357223 0.704766 0.524868 0.029 Uiso 1 1 calc R U . . .
C36 C 0.4365(5) 0.5849(7) 0.51609(18) 0.0263(19) Uani 1 1 d . . . . .
H36A H 0.431719 0.591358 0.496197 0.032 Uiso 1 1 calc R U . C 4
C37 C 0.2786(5) 0.6680(6) 0.59106(18) 0.0213(17) Uani 1 1 d . . . . .
C38 C 0.2094(5) 0.6570(7) 0.57069(19) 0.0249(19) Uani 1 1 d . . . . .
H38A H 0.224400 0.646725 0.550712 0.030 Uiso 1 1 calc R U . . .
H38B H 0.170370 0.715702 0.572668 0.030 Uiso 1 1 calc R U . . .
C39 C 0.1879(5) 0.5495(7) 0.5861(2) 0.032(2) Uani 1 1 d . . . . .
H39A H 0.146604 0.558389 0.600351 0.039 Uiso 1 1 calc R U . . .
H39B H 0.176246 0.487969 0.573201 0.039 Uiso 1 1 calc R U . . .
C40 C 0.2697(4) 0.5448(6) 0.59880(18) 0.0220(18) Uani 1 1 d . . . . .
H40A H 0.305586 0.495840 0.588544 0.026 Uiso 1 1 calc R U . . .
H40B H 0.270673 0.529970 0.619329 0.026 Uiso 1 1 calc R U . . .
C41 C 0.3786(5) 0.7986(6) 0.59352(16) 0.0208(17) Uani 1 1 d . . . . .
C42 C 0.2641(4) 0.7453(7) 0.61521(17) 0.0221(18) Uani 1 1 d . . . . .
C43 C 0.3345(5) 1.0181(7) 0.62570(18) 0.0246(18) Uani 1 1 d . . . . .
H43A H 0.329693 1.035342 0.606245 0.030 Uiso 1 1 calc R U . . .
C44 C 0.3302(4) 0.9083(6) 0.63445(17) 0.0194(17) Uani 1 1 d . . . . .
C45 C 0.3362(5) 0.8819(7) 0.66241(18) 0.0247(18) Uani 1 1 d . . . . .
H45A H 0.333479 0.807690 0.668312 0.030 Uiso 1 1 calc R U . . .
C46 C 0.3461(5) 0.9642(7) 0.68183(18) 0.0267(19) Uani 1 1 d . . . . .
C47 C 0.3509(5) 1.0734(7) 0.67171(18) 0.0251(18) Uani 1 1 d . . . . .
C48 C 0.3533(6) 0.9319(8) 0.7123(2) 0.037(2) Uani 1 1 d . . . . .
C49 C 0.3625(5) 1.1667(7) 0.69023(18) 0.030(2) Uani 1 1 d . . . . .
S3 S 0.42492(13) 0.47443(16) 0.41707(4) 0.0251(5) Uani 1 1 d . . . . .
F3A F 0.2134(5) 0.8190(8) 0.4469(2) 0.034(3) Uani 0.562(12) 1 d . . P D 5
F3B F 0.4661(6) 0.8220(9) 0.4873(2) 0.026(3) Uani 0.438(12) 1 d . . P D 6
F31 F 0.6347(3) 0.2212(4) 0.39388(11) 0.0433(15) Uani 1 1 d . . . . .
F32 F 0.6673(3) 0.1610(4) 0.35329(12) 0.0405(14) Uani 1 1 d . . . . .
F33 F 0.5668(3) 0.0954(4) 0.37361(11) 0.0335(12) Uani 1 1 d . . . . .
O31 O 0.2428(4) 0.8445(5) 0.50434(13) 0.0324(15) Uani 1 1 d . . . . .
O32 O 0.5289(4) 0.6599(5) 0.33129(12) 0.0303(14) Uani 1 1 d . . . . .
N31 N 0.3433(5) 0.9656(6) 0.50485(15) 0.0292(17) Uani 1 1 d . . . . .
H3 H 0.390(5) 0.987(7) 0.4955(18) 0.035 Uiso 1 1 d . U . . .
N32 N 0.4302(4) 0.6779(5) 0.39550(14) 0.0215(15) Uani 1 1 d . . . . .
N33 N 0.4778(4) 0.5521(5) 0.36682(14) 0.0211(15) Uani 1 1 d . . . . .
N34 N 0.4755(4) 0.3260(5) 0.31617(14) 0.0229(15) Uani 1 1 d . . . . .
N35 N 0.5314(4) 0.0697(6) 0.30246(15) 0.0302(17) Uani 1 1 d . . . . .
C3 C 0.3225(6) 1.0176(8) 0.53157(19) 0.039(2) Uani 1 1 d . . . . .
H3A H 0.313905 1.095975 0.528491 0.058 Uiso 1 1 calc R U . . .
H3B H 0.364484 1.007556 0.545194 0.058 Uiso 1 1 calc R U . . .
H3C H 0.275129 0.984204 0.538924 0.058 Uiso 1 1 calc R U . . .
C50 C 0.3043(5) 0.8822(7) 0.49426(18) 0.0266(19) Uani 1 1 d . . . . .
C51 C 0.3367(5) 0.8310(6) 0.46788(16) 0.0201(17) Uani 1 1 d . . . . .
C52 C 0.2914(5) 0.8014(6) 0.44535(18) 0.0211(18) Uani 1 1 d . . . . .
H52A H 0.237551 0.816269 0.446288 0.025 Uiso 1 1 calc R U . D 6
C53 C 0.3198(5) 0.7510(6) 0.42139(18) 0.0227(18) Uani 1 1 d . . . . .
H53A H 0.286364 0.731636 0.406310 0.027 Uiso 1 1 calc R U . . .
C54 C 0.3988(5) 0.7294(6) 0.41992(17) 0.0240(18) Uani 1 1 d . . . . .
C55 C 0.4469(5) 0.7553(7) 0.44192(17) 0.0240(18) Uani 1 1 d . . . . .
H55A H 0.500378 0.738295 0.441163 0.029 Uiso 1 1 calc R U . . .
C56 C 0.4151(5) 0.8076(6) 0.46560(18) 0.0258(19) Uani 1 1 d . . . . .
H56A H 0.448451 0.827859 0.480641 0.031 Uiso 1 1 calc R U . D 5
C57 C 0.4535(5) 0.7389(7) 0.37007(17) 0.0231(18) Uani 1 1 d . . . . .
C58 C 0.5014(5) 0.8435(6) 0.37265(18) 0.0248(19) Uani 1 1 d . . . . .
H58A H 0.556852 0.833402 0.368274 0.030 Uiso 1 1 calc R U . . .
H58B H 0.494410 0.882404 0.390791 0.030 Uiso 1 1 calc R U . . .
C59 C 0.4542(5) 0.8921(7) 0.34820(19) 0.030(2) Uani 1 1 d . . . . .
H59A H 0.436085 0.967705 0.351676 0.036 Uiso 1 1 calc R U . . .
H59B H 0.480017 0.886195 0.329625 0.036 Uiso 1 1 calc R U . . .
C60 C 0.3921(5) 0.8045(7) 0.35323(19) 0.030(2) Uani 1 1 d . . . . .
H60A H 0.374261 0.767590 0.335829 0.036 Uiso 1 1 calc R U . . .
H60B H 0.347950 0.829995 0.364752 0.036 Uiso 1 1 calc R U . . .
C61 C 0.4444(4) 0.5694(6) 0.39344(16) 0.0171(16) Uani 1 1 d . . . . .
C62 C 0.4927(5) 0.6502(6) 0.35284(17) 0.0213(17) Uani 1 1 d . . . . .
C63 C 0.4649(5) 0.4220(6) 0.32896(17) 0.0219(17) Uani 1 1 d . . . . .
H63A H 0.434562 0.475795 0.319628 0.026 Uiso 1 1 calc R U . . .
C64 C 0.4955(4) 0.4474(6) 0.35507(17) 0.0189(16) Uani 1 1 d . . . . .
C65 C 0.5438(5) 0.3728(6) 0.36834(18) 0.0224(18) Uani 1 1 d . . . . .
H65A H 0.567602 0.390031 0.385845 0.027 Uiso 1 1 calc R U . . .
C66 C 0.5564(5) 0.2737(7) 0.35559(18) 0.0232(18) Uani 1 1 d . . . . .
C67 C 0.5208(5) 0.2541(6) 0.32938(18) 0.0221(18) Uani 1 1 d . . . . .
C68 C 0.6060(5) 0.1879(7) 0.3689(2) 0.029(2) Uani 1 1 d . . . . .
C69 C 0.5289(5) 0.1506(7) 0.31465(17) 0.0236(18) Uani 1 1 d . . . . .
S4 S 0.66149(12) 1.02606(16) 0.58466(4) 0.0239(4) Uani 1 1 d . . . . .
F4A F 0.8729(5) 0.6842(7) 0.55480(19) 0.020(3) Uani 0.490(12) 1 d . . P E 7
F4B F 0.6210(6) 0.6773(8) 0.5133(2) 0.035(3) Uani 0.510(12) 1 d . . P E 8
F41 F 0.4213(3) 1.3421(4) 0.64650(12) 0.0403(14) Uani 1 1 d . . . . .
F42 F 0.5249(3) 1.4033(4) 0.62729(11) 0.0348(12) Uani 1 1 d . . . . .
F43 F 0.4575(3) 1.2782(4) 0.60645(12) 0.0403(14) Uani 1 1 d . . . . .
O41 O 0.8443(3) 0.6589(5) 0.49676(13) 0.0297(14) Uani 1 1 d . . . . .
O42 O 0.5621(4) 0.8356(4) 0.67068(12) 0.0299(14) Uani 1 1 d . . . . .
N41 N 0.7446(4) 0.5383(6) 0.49578(16) 0.0278(17) Uani 1 1 d . . . . .
H4 H 0.708(5) 0.513(8) 0.5033(19) 0.033 Uiso 1 1 d . U . . .
N42 N 0.6567(4) 0.8215(5) 0.60600(14) 0.0206(15) Uani 1 1 d . . . . .
N43 N 0.6092(4) 0.9464(5) 0.63468(13) 0.0177(14) Uani 1 1 d . . . . .
N44 N 0.6050(4) 1.1684(5) 0.68661(15) 0.0257(16) Uani 1 1 d . . . . .
N45 N 0.5518(5) 1.4261(6) 0.69945(17) 0.038(2) Uani 1 1 d . . . . .
C4 C 0.7659(6) 0.4847(8) 0.46940(19) 0.041(2) Uani 1 1 d . . . . .
H4A H 0.733122 0.420346 0.466517 0.062 Uiso 1 1 calc R U . . .
H4B H 0.820179 0.462028 0.470274 0.062 Uiso 1 1 calc R U . . .
H4C H 0.758802 0.535874 0.453688 0.062 Uiso 1 1 calc R U . . .
C70 C 0.7841(4) 0.6218(6) 0.50679(17) 0.0187(17) Uani 1 1 d . . . . .
C71 C 0.7483(5) 0.6711(6) 0.53292(17) 0.0219(18) Uani 1 1 d . . . . .
C72 C 0.7961(4) 0.7007(6) 0.55558(17) 0.0214(18) Uani 1 1 d . . . . .
H72A H 0.850003 0.686639 0.554346 0.026 Uiso 1 1 calc R U . E 8
C73 C 0.7669(5) 0.7500(6) 0.57982(17) 0.0231(18) Uani 1 1 d . . . . .
H73A H 0.799962 0.767836 0.595147 0.028 Uiso 1 1 calc R U . . .
C74 C 0.6885(5) 0.7724(6) 0.58101(16) 0.0190(17) Uani 1 1 d . . . . .
C75 C 0.6389(4) 0.7436(6) 0.55885(17) 0.0182(17) Uani 1 1 d . . . . .
H75A H 0.584940 0.757476 0.559963 0.022 Uiso 1 1 calc R U . . .
C76 C 0.6705(4) 0.6949(6) 0.53560(17) 0.0198(17) Uani 1 1 d . . . . .
H76A H 0.637102 0.676455 0.520410 0.024 Uiso 1 1 calc R U . E 7
C77 C 0.6333(5) 0.7594(6) 0.63075(17) 0.0203(17) Uani 1 1 d . . . . .
C78 C 0.5827(5) 0.6538(6) 0.62780(17) 0.0255(19) Uani 1 1 d . . . . .
H78A H 0.527459 0.664827 0.632488 0.031 Uiso 1 1 calc R U . . .
H78B H 0.588688 0.615591 0.609520 0.031 Uiso 1 1 calc R U . . .
C79 C 0.6311(5) 0.6037(7) 0.65213(18) 0.029(2) Uani 1 1 d . . . . .
H79A H 0.606102 0.609526 0.670863 0.035 Uiso 1 1 calc R U . . .
H79B H 0.648474 0.527864 0.648456 0.035 Uiso 1 1 calc R U . . .
C80 C 0.6942(5) 0.6911(6) 0.64688(18) 0.0229(18) Uani 1 1 d . . . . .
H80A H 0.713502 0.726552 0.664283 0.027 Uiso 1 1 calc R U . . .
H80B H 0.737493 0.665250 0.634955 0.027 Uiso 1 1 calc R U . . .
C81 C 0.6421(5) 0.9315(6) 0.60799(16) 0.0215(18) Uani 1 1 d . . . . .
C82 C 0.5967(5) 0.8464(6) 0.64863(18) 0.0239(19) Uani 1 1 d . . . . .
C83 C 0.6188(5) 1.0727(7) 0.67348(18) 0.0264(19) Uani 1 1 d . . . . .
H83A H 0.649602 1.019351 0.682769 0.032 Uiso 1 1 calc R U . . .
C84 C 0.5898(5) 1.0490(6) 0.64688(17) 0.0212(17) Uani 1 1 d . . . . .
C85 C 0.5434(5) 1.1230(6) 0.63289(18) 0.0229(18) Uani 1 1 d . . . . .
H85A H 0.520966 1.106205 0.615113 0.028 Uiso 1 1 calc R U . . .
C86 C 0.5306(5) 1.2249(6) 0.64614(19) 0.0235(19) Uani 1 1 d . . . . .
C87 C 0.5626(5) 1.2424(6) 0.67229(17) 0.0237(18) Uani 1 1 d . . . . .
C88 C 0.4836(5) 1.3106(7) 0.63151(19) 0.0269(19) Uani 1 1 d . . . . .
C89 C 0.5549(5) 1.3458(7) 0.68754(19) 0.029(2) Uani 1 1 d . . . . .
O1 O 0.7015(4) 0.8742(5) 0.35590(12) 0.0327(15) Uani 1 1 d . . . . .
N1 N 0.7322(4) 0.9170(6) 0.31026(14) 0.0303(17) Uani 1 1 d . . . . .
C5 C 0.6845(5) 0.9060(7) 0.33195(18) 0.0271(19) Uani 1 1 d . . . . .
H5A H 0.631946 0.924573 0.328766 0.032 Uiso 1 1 calc R U . . .
C90 C 0.8151(6) 0.8969(13) 0.3127(3) 0.073(4) Uani 1 1 d . . . . .
H90A H 0.827042 0.871751 0.331835 0.109 Uiso 1 1 calc R U . . .
H90B H 0.843390 0.964658 0.308810 0.109 Uiso 1 1 calc R U . . .
H90C H 0.830484 0.840626 0.299071 0.109 Uiso 1 1 calc R U . . .
C91 C 0.7052(5) 0.9547(9) 0.28300(19) 0.038(2) Uani 1 1 d . . . . .
H91A H 0.648964 0.964205 0.283563 0.057 Uiso 1 1 calc R U . . .
H91B H 0.718561 0.900655 0.268542 0.057 Uiso 1 1 calc R U . . .
H91C H 0.729748 1.024792 0.278473 0.057 Uiso 1 1 calc R U . . .
O2 O 0.2119(4) 0.1156(5) 0.70853(15) 0.0420(17) Uani 1 1 d . . . . .
N2 N 0.1266(5) 0.2121(8) 0.73495(17) 0.050(2) Uani 1 1 d . U . . .
C6 C 0.1900(6) 0.1994(8) 0.7195(2) 0.040(2) Uani 1 1 d . U . . .
H6A H 0.221255 0.262386 0.716850 0.048 Uiso 1 1 calc R U . . .
C92 C 0.0784(7) 0.1170(14) 0.7387(2) 0.085(5) Uani 1 1 d . U . . .
H92A H 0.110996 0.051827 0.740556 0.127 Uiso 1 1 calc R U . . .
H92B H 0.044276 0.108806 0.722377 0.127 Uiso 1 1 calc R U . . .
H92C H 0.047202 0.125824 0.755829 0.127 Uiso 1 1 calc R U . . .
C93 C 0.0989(10) 0.3169(13) 0.7439(3) 0.108(7) Uani 1 1 d . U . . .
H93A H 0.138110 0.372696 0.740003 0.161 Uiso 1 1 calc R U . . .
H93B H 0.088193 0.314998 0.764214 0.161 Uiso 1 1 calc R U . . .
H93C H 0.051323 0.334721 0.733678 0.161 Uiso 1 1 calc R U . . .
O3 O 0.3716(4) 0.6106(5) 0.29491(15) 0.0417(17) Uani 1 1 d . . . . .
N3 N 0.4312(4) 0.7430(6) 0.26831(17) 0.0369(19) Uani 1 1 d . . . . .
C7 C 0.4278(6) 0.6461(8) 0.28152(19) 0.037(2) Uani 1 1 d . . . . .
H7A H 0.472327 0.600805 0.280539 0.045 Uiso 1 1 calc R U . . .
C94 C 0.3659(6) 0.8177(10) 0.2684(3) 0.067(4) Uani 1 1 d . . . . .
H94A H 0.324006 0.786571 0.279819 0.100 Uiso 1 1 calc R U . . .
H94B H 0.347716 0.828904 0.249072 0.100 Uiso 1 1 calc R U . . .
H94C H 0.381806 0.887970 0.276508 0.100 Uiso 1 1 calc R U . . .
C95 C 0.5015(6) 0.7814(9) 0.2557(2) 0.049(3) Uani 1 1 d . . . . .
H95A H 0.540307 0.723125 0.256168 0.073 Uiso 1 1 calc R U . . .
H95B H 0.520529 0.845031 0.266151 0.073 Uiso 1 1 calc R U . . .
H95C H 0.491513 0.802368 0.236046 0.073 Uiso 1 1 calc R U . . .
O4 O 0.3841(4) 0.6276(5) 0.64601(12) 0.0296(14) Uani 1 1 d . . . . .
N4 N 0.3563(4) 0.5828(6) 0.69173(15) 0.0317(18) Uani 1 1 d . . . . .
C8 C 0.4022(5) 0.6038(7) 0.67010(19) 0.032(2) Uani 1 1 d . . . . .
H8A H 0.456116 0.599681 0.673785 0.038 Uiso 1 1 calc R U . . .
C96 C 0.2740(6) 0.5861(12) 0.6889(2) 0.065(4) Uani 1 1 d . . . . .
H96A H 0.260470 0.617327 0.670495 0.098 Uiso 1 1 calc R U . . .
H96B H 0.252048 0.631461 0.703912 0.098 Uiso 1 1 calc R U . . .
H96C H 0.253232 0.511705 0.690270 0.098 Uiso 1 1 calc R U . . .
C97 C 0.3851(7) 0.5528(9) 0.71959(19) 0.049(3) Uani 1 1 d . . . . .
H97A H 0.441595 0.548277 0.719091 0.074 Uiso 1 1 calc R U . . .
H97B H 0.363697 0.481593 0.725036 0.074 Uiso 1 1 calc R U . . .
H97C H 0.369269 0.608252 0.733351 0.074 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
S1 C21 1.672(8) . ?
F1A C12 1.310(13) . ?
F1B C16 1.361(11) . ?
F11A C28 1.417(10) . ?
F12A C28 1.335(11) . ?
F13A C28 1.382(10) . ?
F11B C28 1.331(9) . ?
F12B C28 1.405(9) . ?
F13B C28 1.333(9) . ?
O11 C10 1.237(10) . ?
O12 C22 1.213(10) . ?
N11 C10 1.332(11) . ?
N11 C1 1.457(10) . ?
N11 H1 0.86(9) . ?
N12 C21 1.338(10) . ?
N12 C14 1.453(10) . ?
N12 C17 1.455(10) . ?
N13 C21 1.392(10) . ?
N13 C22 1.394(10) . ?
N13 C24 1.418(10) . ?
N14 C23 1.335(11) . ?
N14 C27 1.344(12) . ?
N15 C29 1.140(12) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C10 C11 1.509(11) . ?
C11 C16 1.379(12) . ?
C11 C12 1.385(12) . ?
C12 C13 1.382(12) . ?
C12 H12A 0.9500 . ?
C13 C14 1.375(12) . ?
C13 H13A 0.9500 . ?
C14 C15 1.362(12) . ?
C15 C16 1.371(12) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C22 1.517(11) . ?
C17 C18 1.542(11) . ?
C17 C20 1.554(11) . ?
C18 C19 1.544(12) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.564(11) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C23 C24 1.390(11) . ?
C23 H23A 0.9500 . ?
C24 C25 1.383(12) . ?
C25 C26 1.398(12) . ?
C25 H25A 0.9500 . ?
C26 C27 1.381(13) . ?
C26 C28 1.508(15) . ?
C27 C29 1.467(13) . ?
S2 C41 1.642(8) . ?
F2A C36 1.312(13) . ?
F2B C32 1.361(11) . ?
F21 C48 1.322(10) . ?
F22 C48 1.342(10) . ?
F23 C48 1.343(11) . ?
O21 C30 1.231(10) . ?
O22 C42 1.210(9) . ?
N21 C30 1.323(11) . ?
N21 C2 1.463(10) . ?
N21 H2 0.75(9) . ?
N22 C41 1.345(10) . ?
N22 C34 1.414(10) . ?
N22 C37 1.473(10) . ?
N23 C42 1.382(10) . ?
N23 C41 1.401(10) . ?
N23 C44 1.441(10) . ?
N24 C47 1.331(11) . ?
N24 C43 1.340(10) . ?
N25 C49 1.154(11) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C30 C31 1.507(11) . ?
C31 C36 1.365(11) . ?
C31 C32 1.378(11) . ?
C32 C33 1.372(11) . ?
C32 H32A 0.9500 . ?
C33 C34 1.406(11) . ?
C33 H33A 0.9500 . ?
C34 C35 1.382(12) . ?
C35 C36 1.392(12) . ?
C35 H35A 0.9500 . ?
C36 H36A 0.9500 . ?
C37 C42 1.505(11) . ?
C37 C38 1.544(11) . ?
C37 C40 1.558(10) . ?
C38 C39 1.549(12) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.539(12) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C43 C44 1.406(11) . ?
C43 H43A 0.9500 . ?
C44 C45 1.368(11) . ?
C45 C46 1.375(11) . ?
C45 H45A 0.9500 . ?
C46 C47 1.420(12) . ?
C46 C48 1.504(13) . ?
C47 C49 1.453(11) . ?
S3 C61 1.648(8) . ?
F3A C52 1.368(11) . ?
F3B C56 1.365(13) . ?
F31 C68 1.347(10) . ?
F32 C68 1.334(10) . ?
F33 C68 1.337(9) . ?
O31 C50 1.254(10) . ?
O32 C62 1.204(9) . ?
N31 C50 1.322(11) . ?
N31 C3 1.462(10) . ?
N31 H3 0.96(9) . ?
N32 C61 1.352(10) . ?
N32 C54 1.426(10) . ?
N32 C57 1.473(10) . ?
N33 C62 1.395(10) . ?
N33 C61 1.404(10) . ?
N33 C64 1.429(9) . ?
N34 C63 1.333(10) . ?
N34 C67 1.334(10) . ?
N35 C69 1.146(10) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C50 C51 1.506(11) . ?
C51 C52 1.374(11) . ?
C51 C56 1.391(12) . ?
C52 C53 1.382(12) . ?
C52 H52A 0.9500 . ?
C53 C54 1.394(12) . ?
C53 H53A 0.9500 . ?
C54 C55 1.371(12) . ?
C55 C56 1.404(11) . ?
C55 H55A 0.9500 . ?
C56 H56A 0.9500 . ?
C57 C62 1.518(11) . ?
C57 C58 1.529(11) . ?
C57 C60 1.551(12) . ?
C58 C59 1.537(12) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C59 C60 1.535(12) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C60 H60A 0.9900 . ?
C60 H60B 0.9900 . ?
C63 C64 1.382(11) . ?
C63 H63A 0.9500 . ?
C64 C65 1.387(11) . ?
C65 C66 1.371(11) . ?
C65 H65A 0.9500 . ?
C66 C67 1.407(12) . ?
C66 C68 1.496(12) . ?
C67 C69 1.452(11) . ?
S4 C81 1.634(8) . ?
F4A C72 1.345(11) . ?
F4B C76 1.376(12) . ?
F41 C88 1.347(10) . ?
F42 C88 1.355(10) . ?
F43 C88 1.331(10) . ?
O41 C70 1.231(9) . ?
O42 C82 1.212(10) . ?
N41 C70 1.335(10) . ?
N41 C4 1.460(11) . ?
N41 H4 0.79(9) . ?
N42 C81 1.371(10) . ?
N42 C74 1.437(10) . ?
N42 C77 1.455(10) . ?
N43 C81 1.400(10) . ?
N43 C82 1.406(10) . ?
N43 C84 1.422(9) . ?
N44 C83 1.347(10) . ?
N44 C87 1.348(11) . ?
N45 C89 1.133(11) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C70 C71 1.510(11) . ?
C71 C76 1.385(11) . ?
C71 C72 1.403(11) . ?
C72 C73 1.392(11) . ?
C72 H72A 0.9500 . ?
C73 C74 1.386(11) . ?
C73 H73A 0.9500 . ?
C74 C75 1.402(11) . ?
C75 C76 1.367(11) . ?
C75 H75A 0.9500 . ?
C76 H76A 0.9500 . ?
C77 C82 1.501(11) . ?
C77 C80 1.547(11) . ?
C77 C78 1.566(11) . ?
C78 C79 1.552(12) . ?
C78 H78A 0.9900 . ?
C78 H78B 0.9900 . ?
C79 C80 1.549(12) . ?
C79 H79A 0.9900 . ?
C79 H79B 0.9900 . ?
C80 H80A 0.9900 . ?
C80 H80B 0.9900 . ?
C83 C84 1.388(12) . ?
C83 H83A 0.9500 . ?
C84 C85 1.380(11) . ?
C85 C86 1.412(11) . ?
C85 H85A 0.9500 . ?
C86 C87 1.374(12) . ?
C86 C88 1.497(11) . ?
C87 C89 1.462(11) . ?
O1 C5 1.236(10) . ?
N1 C5 1.325(11) . ?
N1 C91 1.449(10) . ?
N1 C90 1.461(13) . ?
C5 H5A 0.9500 . ?
C90 H90A 0.9800 . ?
C90 H90B 0.9800 . ?
C90 H90C 0.9800 . ?
C91 H91A 0.9800 . ?
C91 H91B 0.9800 . ?
C91 H91C 0.9800 . ?
O2 C6 1.210(11) . ?
N2 C6 1.326(12) . ?
N2 C93 1.432(15) . ?
N2 C92 1.442(16) . ?
C6 H6A 0.9500 . ?
C92 H92A 0.9800 . ?
C92 H92B 0.9800 . ?
C92 H92C 0.9800 . ?
C93 H93A 0.9800 . ?
C93 H93B 0.9800 . ?
C93 H93C 0.9800 . ?
O3 C7 1.241(11) . ?
N3 C7 1.340(11) . ?
N3 C95 1.435(12) . ?
N3 C94 1.453(12) . ?
C7 H7A 0.9500 . ?
C94 H94A 0.9800 . ?
C94 H94B 0.9800 . ?
C94 H94C 0.9800 . ?
C95 H95A 0.9800 . ?
C95 H95B 0.9800 . ?
C95 H95C 0.9800 . ?
O4 C8 1.220(10) . ?
N4 C8 1.323(11) . ?
N4 C96 1.430(13) . ?
N4 C97 1.458(11) . ?
C8 H8A 0.9500 . ?
C96 H96A 0.9800 . ?
C96 H96B 0.9800 . ?
C96 H96C 0.9800 . ?
C97 H97A 0.9800 . ?
C97 H97B 0.9800 . ?
C97 H97C 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
C10 N11 C1 121.3(8) . . ?
C10 N11 H1 118(6) . . ?
C1 N11 H1 121(6) . . ?
C21 N12 C14 123.5(7) . . ?
C21 N12 C17 112.6(7) . . ?
C14 N12 C17 122.0(6) . . ?
C21 N13 C22 110.9(6) . . ?
C21 N13 C24 123.2(7) . . ?
C22 N13 C24 124.1(7) . . ?
C23 N14 C27 116.5(8) . . ?
N11 C1 H1A 109.5 . . ?
N11 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N11 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O11 C10 N11 123.8(8) . . ?
O11 C10 C11 119.6(7) . . ?
N11 C10 C11 116.6(7) . . ?
C16 C11 C12 116.8(8) . . ?
C16 C11 C10 121.1(8) . . ?
C12 C11 C10 122.0(7) . . ?
F1A C12 C13 118.7(9) . . ?
F1A C12 C11 119.3(9) . . ?
C13 C12 C11 121.8(8) . . ?
C13 C12 H12A 119.1 . . ?
C11 C12 H12A 119.1 . . ?
C14 C13 C12 118.1(8) . . ?
C14 C13 H13A 121.0 . . ?
C12 C13 H13A 121.0 . . ?
C15 C14 C13 122.4(8) . . ?
C15 C14 N12 118.1(7) . . ?
C13 C14 N12 119.3(7) . . ?
C14 C15 C16 117.7(8) . . ?
C14 C15 H15A 121.1 . . ?
C16 C15 H15A 121.1 . . ?
F1B C16 C15 120.8(8) . . ?
F1B C16 C11 115.1(8) . . ?
C15 C16 C11 123.2(8) . . ?
C15 C16 H16A 118.4 . . ?
C11 C16 H16A 118.4 . . ?
N12 C17 C22 101.8(6) . . ?
N12 C17 C18 121.5(7) . . ?
C22 C17 C18 114.1(7) . . ?
N12 C17 C20 118.6(7) . . ?
C22 C17 C20 112.1(7) . . ?
C18 C17 C20 89.1(6) . . ?
C17 C18 C19 89.5(6) . . ?
C17 C18 H18A 113.7 . . ?
C19 C18 H18A 113.7 . . ?
C17 C18 H18B 113.7 . . ?
C19 C18 H18B 113.7 . . ?
H18A C18 H18B 111.0 . . ?
C18 C19 C20 88.7(6) . . ?
C18 C19 H19A 113.9 . . ?
C20 C19 H19A 113.9 . . ?
C18 C19 H19B 113.9 . . ?
C20 C19 H19B 113.9 . . ?
H19A C19 H19B 111.1 . . ?
C17 C20 C19 88.4(6) . . ?
C17 C20 H20A 113.9 . . ?
C19 C20 H20A 113.9 . . ?
C17 C20 H20B 113.9 . . ?
C19 C20 H20B 113.9 . . ?
H20A C20 H20B 111.1 . . ?
N12 C21 N13 108.0(7) . . ?
N12 C21 S1 127.7(6) . . ?
N13 C21 S1 124.2(6) . . ?
O12 C22 N13 125.8(7) . . ?
O12 C22 C17 128.1(8) . . ?
N13 C22 C17 106.2(7) . . ?
N14 C23 C24 123.5(8) . . ?
N14 C23 H23A 118.3 . . ?
C24 C23 H23A 118.3 . . ?
C25 C24 C23 119.2(8) . . ?
C25 C24 N13 120.4(7) . . ?
C23 C24 N13 120.4(8) . . ?
C24 C25 C26 118.3(9) . . ?
C24 C25 H25A 120.9 . . ?
C26 C25 H25A 120.9 . . ?
C27 C26 C25 118.0(9) . . ?
C27 C26 C28 121.8(8) . . ?
C25 C26 C28 120.0(8) . . ?
N14 C27 C26 124.6(8) . . ?
N14 C27 C29 115.0(9) . . ?
C26 C27 C29 120.4(9) . . ?
F11B C28 F13B 111.5(9) . . ?
F12A C28 F13A 106.1(10) . . ?
F11B C28 F12B 104.2(8) . . ?
F13B C28 F12B 108.3(8) . . ?
F12A C28 F11A 104.9(10) . . ?
F13A C28 F11A 101.5(9) . . ?
F11B C28 C26 112.0(8) . . ?
F13B C28 C26 114.8(10) . . ?
F12A C28 C26 126.5(13) . . ?
F13A C28 C26 105.9(12) . . ?
F12B C28 C26 105.2(9) . . ?
F11A C28 C26 109.2(10) . . ?
N15 C29 C27 174.9(11) . . ?
C30 N21 C2 121.5(7) . . ?
C30 N21 H2 117(8) . . ?
C2 N21 H2 121(8) . . ?
C41 N22 C34 124.5(7) . . ?
C41 N22 C37 113.5(6) . . ?
C34 N22 C37 121.0(6) . . ?
C42 N23 C41 113.4(6) . . ?
C42 N23 C44 122.3(7) . . ?
C41 N23 C44 123.4(6) . . ?
C47 N24 C43 119.0(7) . . ?
N21 C2 H2A 109.5 . . ?
N21 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N21 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O21 C30 N21 123.9(8) . . ?
O21 C30 C31 119.1(8) . . ?
N21 C30 C31 117.0(7) . . ?
C36 C31 C32 116.6(7) . . ?
C36 C31 C30 123.7(8) . . ?
C32 C31 C30 119.7(7) . . ?
F2B C32 C33 119.2(8) . . ?
F2B C32 C31 117.2(8) . . ?
C33 C32 C31 123.4(8) . . ?
C33 C32 H32A 118.3 . . ?
C31 C32 H32A 118.3 . . ?
C32 C33 C34 118.3(8) . . ?
C32 C33 H33A 120.9 . . ?
C34 C33 H33A 120.9 . . ?
C35 C34 C33 120.2(7) . . ?
C35 C34 N22 121.3(7) . . ?
C33 C34 N22 118.5(7) . . ?
C34 C35 C36 118.1(8) . . ?
C34 C35 H35A 120.9 . . ?
C36 C35 H35A 120.9 . . ?
F2A C36 C31 118.3(9) . . ?
F2A C36 C35 117.9(9) . . ?
C31 C36 C35 123.5(8) . . ?
C31 C36 H36A 118.3 . . ?
C35 C36 H36A 118.3 . . ?
N22 C37 C42 101.5(6) . . ?
N22 C37 C38 119.8(7) . . ?
C42 C37 C38 113.7(7) . . ?
N22 C37 C40 119.1(6) . . ?
C42 C37 C40 114.3(7) . . ?
C38 C37 C40 89.2(6) . . ?
C37 C38 C39 88.0(6) . . ?
C37 C38 H38A 114.0 . . ?
C39 C38 H38A 114.0 . . ?
C37 C38 H38B 114.0 . . ?
C39 C38 H38B 114.0 . . ?
H38A C38 H38B 111.2 . . ?
C40 C39 C38 89.7(6) . . ?
C40 C39 H39A 113.7 . . ?
C38 C39 H39A 113.7 . . ?
C40 C39 H39B 113.7 . . ?
C38 C39 H39B 113.7 . . ?
H39A C39 H39B 110.9 . . ?
C39 C40 C37 87.8(6) . . ?
C39 C40 H40A 114.0 . . ?
C37 C40 H40A 114.0 . . ?
C39 C40 H40B 114.0 . . ?
C37 C40 H40B 114.0 . . ?
H40A C40 H40B 111.2 . . ?
N22 C41 N23 105.3(7) . . ?
N22 C41 S2 128.6(6) . . ?
N23 C41 S2 126.1(6) . . ?
O22 C42 N23 126.3(7) . . ?
O22 C42 C37 128.0(7) . . ?
N23 C42 C37 105.7(7) . . ?
N24 C43 C44 120.8(8) . . ?
N24 C43 H43A 119.6 . . ?
C44 C43 H43A 119.6 . . ?
C45 C44 C43 120.5(7) . . ?
C45 C44 N23 119.7(7) . . ?
C43 C44 N23 119.8(7) . . ?
C44 C45 C46 119.0(8) . . ?
C44 C45 H45A 120.5 . . ?
C46 C45 H45A 120.5 . . ?
C45 C46 C47 118.0(8) . . ?
C45 C46 C48 117.5(8) . . ?
C47 C46 C48 124.5(7) . . ?
N24 C47 C46 122.7(7) . . ?
N24 C47 C49 114.5(7) . . ?
C46 C47 C49 122.8(8) . . ?
F21 C48 F22 106.3(7) . . ?
F21 C48 F23 107.3(7) . . ?
F22 C48 F23 106.8(8) . . ?
F21 C48 C46 114.2(8) . . ?
F22 C48 C46 110.6(7) . . ?
F23 C48 C46 111.2(8) . . ?
N25 C49 C47 175.0(10) . . ?
C50 N31 C3 122.6(8) . . ?
C50 N31 H3 118(5) . . ?
C3 N31 H3 120(6) . . ?
C61 N32 C54 124.1(7) . . ?
C61 N32 C57 112.8(6) . . ?
C54 N32 C57 123.0(6) . . ?
C62 N33 C61 112.0(6) . . ?
C62 N33 C64 123.0(6) . . ?
C61 N33 C64 125.0(6) . . ?
C63 N34 C67 116.6(7) . . ?
N31 C3 H3A 109.5 . . ?
N31 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N31 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O31 C50 N31 124.9(8) . . ?
O31 C50 C51 118.6(8) . . ?
N31 C50 C51 116.5(7) . . ?
C52 C51 C56 116.3(7) . . ?
C52 C51 C50 122.9(7) . . ?
C56 C51 C50 120.8(7) . . ?
F3A C52 C51 118.8(8) . . ?
F3A C52 C53 117.6(8) . . ?
C51 C52 C53 123.6(8) . . ?
C51 C52 H52A 118.2 . . ?
C53 C52 H52A 118.2 . . ?
C52 C53 C54 118.3(8) . . ?
C52 C53 H53A 120.8 . . ?
C54 C53 H53A 120.8 . . ?
C55 C54 C53 120.9(8) . . ?
C55 C54 N32 119.2(8) . . ?
C53 C54 N32 119.9(8) . . ?
C54 C55 C56 118.4(8) . . ?
C54 C55 H55A 120.8 . . ?
C56 C55 H55A 120.8 . . ?
F3B C56 C51 123.1(9) . . ?
F3B C56 C55 114.0(9) . . ?
C51 C56 C55 122.5(8) . . ?
C51 C56 H56A 118.7 . . ?
C55 C56 H56A 118.7 . . ?
N32 C57 C62 101.6(6) . . ?
N32 C57 C58 120.4(7) . . ?
C62 C57 C58 113.4(7) . . ?
N32 C57 C60 119.7(7) . . ?
C62 C57 C60 113.5(7) . . ?
C58 C57 C60 88.8(6) . . ?
C57 C58 C59 88.5(6) . . ?
C57 C58 H58A 113.9 . . ?
C59 C58 H58A 113.9 . . ?
C57 C58 H58B 113.9 . . ?
C59 C58 H58B 113.9 . . ?
H58A C58 H58B 111.1 . . ?
C60 C59 C58 89.2(6) . . ?
C60 C59 H59A 113.8 . . ?
C58 C59 H59A 113.8 . . ?
C60 C59 H59B 113.8 . . ?
C58 C59 H59B 113.8 . . ?
H59A C59 H59B 111.0 . . ?
C59 C60 C57 87.8(6) . . ?
C59 C60 H60A 114.0 . . ?
C57 C60 H60A 114.0 . . ?
C59 C60 H60B 114.0 . . ?
C57 C60 H60B 114.0 . . ?
H60A C60 H60B 111.2 . . ?
N32 C61 N33 106.7(6) . . ?
N32 C61 S3 127.2(6) . . ?
N33 C61 S3 126.1(6) . . ?
O32 C62 N33 125.8(7) . . ?
O32 C62 C57 128.3(7) . . ?
N33 C62 C57 105.9(7) . . ?
N34 C63 C64 123.5(7) . . ?
N34 C63 H63A 118.3 . . ?
C64 C63 H63A 118.3 . . ?
C63 C64 C65 119.4(7) . . ?
C63 C64 N33 117.9(7) . . ?
C65 C64 N33 122.7(7) . . ?
C66 C65 C64 118.4(8) . . ?
C66 C65 H65A 120.8 . . ?
C64 C65 H65A 120.8 . . ?
C65 C66 C67 118.1(7) . . ?
C65 C66 C68 121.6(8) . . ?
C67 C66 C68 120.3(7) . . ?
N34 C67 C66 124.0(7) . . ?
N34 C67 C69 113.9(7) . . ?
C66 C67 C69 122.1(8) . . ?
F32 C68 F33 106.7(7) . . ?
F32 C68 F31 105.6(7) . . ?
F33 C68 F31 107.2(7) . . ?
F32 C68 C66 113.2(8) . . ?
F33 C68 C66 111.8(7) . . ?
F31 C68 C66 111.8(7) . . ?
N35 C69 C67 176.3(10) . . ?
C70 N41 C4 123.3(8) . . ?
C70 N41 H4 122(7) . . ?
C4 N41 H4 114(7) . . ?
C81 N42 C74 122.4(6) . . ?
C81 N42 C77 113.9(6) . . ?
C74 N42 C77 123.6(6) . . ?
C81 N43 C82 112.0(6) . . ?
C81 N43 C84 125.4(6) . . ?
C82 N43 C84 122.6(6) . . ?
C83 N44 C87 116.5(7) . . ?
N41 C4 H4A 109.5 . . ?
N41 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N41 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O41 C70 N41 124.3(8) . . ?
O41 C70 C71 121.1(7) . . ?
N41 C70 C71 114.5(7) . . ?
C76 C71 C72 116.7(7) . . ?
C76 C71 C70 123.9(7) . . ?
C72 C71 C70 119.3(7) . . ?
F4A C72 C73 116.5(8) . . ?
F4A C72 C71 121.5(8) . . ?
C73 C72 C71 122.0(7) . . ?
C73 C72 H72A 119.0 . . ?
C71 C72 H72A 119.0 . . ?
C74 C73 C72 118.3(7) . . ?
C74 C73 H73A 120.8 . . ?
C72 C73 H73A 120.8 . . ?
C73 C74 C75 121.3(7) . . ?
C73 C74 N42 119.4(7) . . ?
C75 C74 N42 119.2(7) . . ?
C76 C75 C74 118.0(7) . . ?
C76 C75 H75A 121.0 . . ?
C74 C75 H75A 121.0 . . ?
C75 C76 F4B 116.0(8) . . ?
C75 C76 C71 123.7(8) . . ?
F4B C76 C71 120.2(8) . . ?
C75 C76 H76A 118.2 . . ?
C71 C76 H76A 118.2 . . ?
N42 C77 C82 101.7(6) . . ?
N42 C77 C80 119.4(7) . . ?
C82 C77 C80 113.0(7) . . ?
N42 C77 C78 120.9(7) . . ?
C82 C77 C78 113.5(7) . . ?
C80 C77 C78 88.9(6) . . ?
C79 C78 C77 87.5(6) . . ?
C79 C78 H78A 114.1 . . ?
C77 C78 H78A 114.1 . . ?
C79 C78 H78B 114.1 . . ?
C77 C78 H78B 114.1 . . ?
H78A C78 H78B 111.2 . . ?
C80 C79 C78 89.4(6) . . ?
C80 C79 H79A 113.8 . . ?
C78 C79 H79A 113.8 . . ?
C80 C79 H79B 113.8 . . ?
C78 C79 H79B 113.8 . . ?
H79A C79 H79B 111.0 . . ?
C77 C80 C79 88.3(6) . . ?
C77 C80 H80A 113.9 . . ?
C79 C80 H80A 113.9 . . ?
C77 C80 H80B 113.9 . . ?
C79 C80 H80B 113.9 . . ?
H80A C80 H80B 111.1 . . ?
N42 C81 N43 105.3(6) . . ?
N42 C81 S4 127.5(6) . . ?
N43 C81 S4 127.1(6) . . ?
O42 C82 N43 125.2(7) . . ?
O42 C82 C77 128.2(7) . . ?
N43 C82 C77 106.6(7) . . ?
N44 C83 C84 122.5(8) . . ?
N44 C83 H83A 118.8 . . ?
C84 C83 H83A 118.8 . . ?
C85 C84 C83 120.7(7) . . ?
C85 C84 N43 121.4(7) . . ?
C83 C84 N43 117.9(7) . . ?
C84 C85 C86 117.1(8) . . ?
C84 C85 H85A 121.5 . . ?
C86 C85 H85A 121.5 . . ?
C87 C86 C85 118.4(8) . . ?
C87 C86 C88 121.9(7) . . ?
C85 C86 C88 119.7(8) . . ?
N44 C87 C86 124.7(7) . . ?
N44 C87 C89 112.4(7) . . ?
C86 C87 C89 122.9(8) . . ?
F43 C88 F41 106.5(7) . . ?
F43 C88 F42 107.2(7) . . ?
F41 C88 F42 105.2(6) . . ?
F43 C88 C86 112.9(7) . . ?
F41 C88 C86 113.0(7) . . ?
F42 C88 C86 111.5(7) . . ?
N45 C89 C87 177.4(11) . . ?
C5 N1 C91 121.6(8) . . ?
C5 N1 C90 122.2(8) . . ?
C91 N1 C90 116.2(8) . . ?
O1 C5 N1 126.7(8) . . ?
O1 C5 H5A 116.6 . . ?
N1 C5 H5A 116.6 . . ?
N1 C90 H90A 109.5 . . ?
N1 C90 H90B 109.5 . . ?
H90A C90 H90B 109.5 . . ?
N1 C90 H90C 109.5 . . ?
H90A C90 H90C 109.5 . . ?
H90B C90 H90C 109.5 . . ?
N1 C91 H91A 109.5 . . ?
N1 C91 H91B 109.5 . . ?
H91A C91 H91B 109.5 . . ?
N1 C91 H91C 109.5 . . ?
H91A C91 H91C 109.5 . . ?
H91B C91 H91C 109.5 . . ?
C6 N2 C93 123.1(12) . . ?
C6 N2 C92 116.9(10) . . ?
C93 N2 C92 119.3(11) . . ?
O2 C6 N2 126.6(10) . . ?
O2 C6 H6A 116.7 . . ?
N2 C6 H6A 116.7 . . ?
N2 C92 H92A 109.5 . . ?
N2 C92 H92B 109.5 . . ?
H92A C92 H92B 109.5 . . ?
N2 C92 H92C 109.5 . . ?
H92A C92 H92C 109.5 . . ?
H92B C92 H92C 109.5 . . ?
N2 C93 H93A 109.5 . . ?
N2 C93 H93B 109.5 . . ?
H93A C93 H93B 109.5 . . ?
N2 C93 H93C 109.5 . . ?
H93A C93 H93C 109.5 . . ?
H93B C93 H93C 109.5 . . ?
C7 N3 C95 121.4(8) . . ?
C7 N3 C94 121.3(8) . . ?
C95 N3 C94 117.1(8) . . ?
O3 C7 N3 125.6(9) . . ?
O3 C7 H7A 117.2 . . ?
N3 C7 H7A 117.2 . . ?
N3 C94 H94A 109.5 . . ?
N3 C94 H94B 109.5 . . ?
H94A C94 H94B 109.5 . . ?
N3 C94 H94C 109.5 . . ?
H94A C94 H94C 109.5 . . ?
H94B C94 H94C 109.5 . . ?
N3 C95 H95A 109.5 . . ?
N3 C95 H95B 109.5 . . ?
H95A C95 H95B 109.5 . . ?
N3 C95 H95C 109.5 . . ?
H95A C95 H95C 109.5 . . ?
H95B C95 H95C 109.5 . . ?
C8 N4 C96 121.3(8) . . ?
C8 N4 C97 123.1(8) . . ?
C96 N4 C97 115.6(8) . . ?
O4 C8 N4 128.1(9) . . ?
O4 C8 H8A 115.9 . . ?
N4 C8 H8A 115.9 . . ?
N4 C96 H96A 109.5 . . ?
N4 C96 H96B 109.5 . . ?
H96A C96 H96B 109.5 . . ?
N4 C96 H96C 109.5 . . ?
H96A C96 H96C 109.5 . . ?
H96B C96 H96C 109.5 . . ?
N4 C97 H97A 109.5 . . ?
N4 C97 H97B 109.5 . . ?
H97A C97 H97B 109.5 . . ?
N4 C97 H97C 109.5 . . ?
H97A C97 H97C 109.5 . . ?
H97B C97 H97C 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
C1 N11 C10 O11 2.8(13) . . . . ?
C1 N11 C10 C11 -178.1(7) . . . . ?
O11 C10 C11 C16 43.4(12) . . . . ?
N11 C10 C11 C16 -135.7(8) . . . . ?
O11 C10 C11 C12 -131.6(9) . . . . ?
N11 C10 C11 C12 49.3(11) . . . . ?
C16 C11 C12 F1A 173.6(10) . . . . ?
C10 C11 C12 F1A -11.2(14) . . . . ?
C16 C11 C12 C13 -1.7(13) . . . . ?
C10 C11 C12 C13 173.5(8) . . . . ?
F1A C12 C13 C14 -174.8(10) . . . . ?
C11 C12 C13 C14 0.5(14) . . . . ?
C12 C13 C14 C15 1.3(14) . . . . ?
C12 C13 C14 N12 175.9(8) . . . . ?
C21 N12 C14 C15 -81.1(10) . . . . ?
C17 N12 C14 C15 82.2(10) . . . . ?
C21 N12 C14 C13 104.0(10) . . . . ?
C17 N12 C14 C13 -92.6(9) . . . . ?
C13 C14 C15 C16 -1.9(13) . . . . ?
N12 C14 C15 C16 -176.5(7) . . . . ?
C14 C15 C16 F1B 169.5(9) . . . . ?
C14 C15 C16 C11 0.6(13) . . . . ?
C12 C11 C16 F1B -168.3(8) . . . . ?
C10 C11 C16 F1B 16.4(12) . . . . ?
C12 C11 C16 C15 1.1(13) . . . . ?
C10 C11 C16 C15 -174.1(8) . . . . ?
C21 N12 C17 C22 2.2(8) . . . . ?
C14 N12 C17 C22 -162.8(7) . . . . ?
C21 N12 C17 C18 130.3(8) . . . . ?
C14 N12 C17 C18 -34.7(11) . . . . ?
C21 N12 C17 C20 -121.4(8) . . . . ?
C14 N12 C17 C20 73.6(9) . . . . ?
N12 C17 C18 C19 139.2(8) . . . . ?
C22 C17 C18 C19 -98.3(8) . . . . ?
C20 C17 C18 C19 15.7(7) . . . . ?
C17 C18 C19 C20 -15.6(6) . . . . ?
N12 C17 C20 C19 -141.4(7) . . . . ?
C22 C17 C20 C19 100.3(7) . . . . ?
C18 C17 C20 C19 -15.5(6) . . . . ?
C18 C19 C20 C17 15.4(6) . . . . ?
C14 N12 C21 N13 166.7(7) . . . . ?
C17 N12 C21 N13 1.9(9) . . . . ?
C14 N12 C21 S1 -14.3(12) . . . . ?
C17 N12 C21 S1 -179.0(6) . . . . ?
C22 N13 C21 N12 -5.7(9) . . . . ?
C24 N13 C21 N12 -171.1(7) . . . . ?
C22 N13 C21 S1 175.1(6) . . . . ?
C24 N13 C21 S1 9.7(11) . . . . ?
C21 N13 C22 O12 -174.0(8) . . . . ?
C24 N13 C22 O12 -8.8(13) . . . . ?
C21 N13 C22 C17 7.0(8) . . . . ?
C24 N13 C22 C17 172.2(7) . . . . ?
N12 C17 C22 O12 175.7(8) . . . . ?
C18 C17 C22 O12 43.0(12) . . . . ?
C20 C17 C22 O12 -56.5(11) . . . . ?
N12 C17 C22 N13 -5.4(8) . . . . ?
C18 C17 C22 N13 -138.1(7) . . . . ?
C20 C17 C22 N13 122.5(7) . . . . ?
C27 N14 C23 C24 1.6(13) . . . . ?
N14 C23 C24 C25 -1.9(14) . . . . ?
N14 C23 C24 N13 177.7(8) . . . . ?
C21 N13 C24 C25 103.3(10) . . . . ?
C22 N13 C24 C25 -60.2(12) . . . . ?
C21 N13 C24 C23 -76.3(11) . . . . ?
C22 N13 C24 C23 120.3(9) . . . . ?
C23 C24 C25 C26 0.8(14) . . . . ?
N13 C24 C25 C26 -178.8(9) . . . . ?
C24 C25 C26 C27 0.4(15) . . . . ?
C24 C25 C26 C28 175.1(9) . . . . ?
C23 N14 C27 C26 -0.2(14) . . . . ?
C23 N14 C27 C29 -177.6(8) . . . . ?
C25 C26 C27 N14 -0.8(15) . . . . ?
C28 C26 C27 N14 -175.3(8) . . . . ?
C25 C26 C27 C29 176.5(9) . . . . ?
C28 C26 C27 C29 2.0(14) . . . . ?
C27 C26 C28 F11B 166.6(10) . . . . ?
C25 C26 C28 F11B -7.8(14) . . . . ?
C27 C26 C28 F13B -65.0(13) . . . . ?
C25 C26 C28 F13B 120.6(11) . . . . ?
C27 C26 C28 F12A 73.1(15) . . . . ?
C25 C26 C28 F12A -101.3(15) . . . . ?
C27 C26 C28 F13A -51.7(14) . . . . ?
C25 C26 C28 F13A 133.9(12) . . . . ?
C27 C26 C28 F12B 54.0(12) . . . . ?
C25 C26 C28 F12B -120.5(10) . . . . ?
C27 C26 C28 F11A -160.2(13) . . . . ?
C25 C26 C28 F11A 25.4(15) . . . . ?
C2 N21 C30 O21 -1.9(14) . . . . ?
C2 N21 C30 C31 176.4(7) . . . . ?
O21 C30 C31 C36 129.0(9) . . . . ?
N21 C30 C31 C36 -49.4(12) . . . . ?
O21 C30 C31 C32 -47.8(11) . . . . ?
N21 C30 C31 C32 133.8(8) . . . . ?
C36 C31 C32 F2B 172.4(8) . . . . ?
C30 C31 C32 F2B -10.6(12) . . . . ?
C36 C31 C32 C33 -2.0(12) . . . . ?
C30 C31 C32 C33 175.0(8) . . . . ?
F2B C32 C33 C34 -173.1(8) . . . . ?
C31 C32 C33 C34 1.2(12) . . . . ?
C32 C33 C34 C35 0.2(12) . . . . ?
C32 C33 C34 N22 177.8(7) . . . . ?
C41 N22 C34 C35 -99.9(10) . . . . ?
C37 N22 C34 C35 91.8(9) . . . . ?
C41 N22 C34 C33 82.6(10) . . . . ?
C37 N22 C34 C33 -85.7(9) . . . . ?
C33 C34 C35 C36 -0.8(12) . . . . ?
N22 C34 C35 C36 -178.2(7) . . . . ?
C32 C31 C36 F2A -172.6(10) . . . . ?
C30 C31 C36 F2A 10.5(14) . . . . ?
C32 C31 C36 C35 1.4(13) . . . . ?
C30 C31 C36 C35 -175.5(8) . . . . ?
C34 C35 C36 F2A 174.0(10) . . . . ?
C34 C35 C36 C31 0.0(13) . . . . ?
C41 N22 C37 C42 -4.8(8) . . . . ?
C34 N22 C37 C42 164.7(7) . . . . ?
C41 N22 C37 C38 121.3(8) . . . . ?
C34 N22 C37 C38 -69.2(9) . . . . ?
C41 N22 C37 C40 -131.2(8) . . . . ?
C34 N22 C37 C40 38.3(11) . . . . ?
N22 C37 C38 C39 140.5(7) . . . . ?
C42 C37 C38 C39 -99.3(7) . . . . ?
C40 C37 C38 C39 17.0(6) . . . . ?
C37 C38 C39 C40 -17.2(6) . . . . ?
C38 C39 C40 C37 17.1(6) . . . . ?
N22 C37 C40 C39 -141.3(7) . . . . ?
C42 C37 C40 C39 98.6(7) . . . . ?
C38 C37 C40 C39 -17.1(6) . . . . ?
C34 N22 C41 N23 -168.2(7) . . . . ?
C37 N22 C41 N23 0.8(9) . . . . ?
C34 N22 C41 S2 10.6(12) . . . . ?
C37 N22 C41 S2 179.6(6) . . . . ?
C42 N23 C41 N22 4.1(9) . . . . ?
C44 N23 C41 N22 173.6(7) . . . . ?
C42 N23 C41 S2 -174.7(6) . . . . ?
C44 N23 C41 S2 -5.3(11) . . . . ?
C41 N23 C42 O22 174.2(8) . . . . ?
C44 N23 C42 O22 4.6(12) . . . . ?
C41 N23 C42 C37 -7.1(9) . . . . ?
C44 N23 C42 C37 -176.7(7) . . . . ?
N22 C37 C42 O22 -174.5(8) . . . . ?
C38 C37 C42 O22 55.4(11) . . . . ?
C40 C37 C42 O22 -45.1(11) . . . . ?
N22 C37 C42 N23 6.8(8) . . . . ?
C38 C37 C42 N23 -123.2(7) . . . . ?
C40 C37 C42 N23 136.3(7) . . . . ?
C47 N24 C43 C44 -0.7(11) . . . . ?
N24 C43 C44 C45 0.7(12) . . . . ?
N24 C43 C44 N23 -177.3(7) . . . . ?
C42 N23 C44 C45 55.1(10) . . . . ?
C41 N23 C44 C45 -113.4(9) . . . . ?
C42 N23 C44 C43 -126.9(8) . . . . ?
C41 N23 C44 C43 64.5(10) . . . . ?
C43 C44 C45 C46 0.2(12) . . . . ?
N23 C44 C45 C46 178.1(7) . . . . ?
C44 C45 C46 C47 -0.9(12) . . . . ?
C44 C45 C46 C48 -179.4(8) . . . . ?
C43 N24 C47 C46 0.0(12) . . . . ?
C43 N24 C47 C49 179.9(7) . . . . ?
C45 C46 C47 N24 0.9(13) . . . . ?
C48 C46 C47 N24 179.2(8) . . . . ?
C45 C46 C47 C49 -179.1(8) . . . . ?
C48 C46 C47 C49 -0.8(14) . . . . ?
C45 C46 C48 F21 159.5(8) . . . . ?
C47 C46 C48 F21 -18.8(13) . . . . ?
C45 C46 C48 F22 39.7(11) . . . . ?
C47 C46 C48 F22 -138.6(9) . . . . ?
C45 C46 C48 F23 -78.8(10) . . . . ?
C47 C46 C48 F23 102.9(10) . . . . ?
C3 N31 C50 O31 5.9(14) . . . . ?
C3 N31 C50 C51 -174.9(8) . . . . ?
O31 C50 C51 C52 42.4(11) . . . . ?
N31 C50 C51 C52 -136.9(8) . . . . ?
O31 C50 C51 C56 -135.3(9) . . . . ?
N31 C50 C51 C56 45.5(11) . . . . ?
C56 C51 C52 F3A 177.8(8) . . . . ?
C50 C51 C52 F3A 0.0(12) . . . . ?
C56 C51 C52 C53 0.0(11) . . . . ?
C50 C51 C52 C53 -177.8(7) . . . . ?
F3A C52 C53 C54 -178.0(8) . . . . ?
C51 C52 C53 C54 -0.2(12) . . . . ?
C52 C53 C54 C55 1.3(12) . . . . ?
C52 C53 C54 N32 -179.8(7) . . . . ?
C61 N32 C54 C55 81.9(10) . . . . ?
C57 N32 C54 C55 -95.8(9) . . . . ?
C61 N32 C54 C53 -97.0(10) . . . . ?
C57 N32 C54 C53 85.3(10) . . . . ?
C53 C54 C55 C56 -2.2(12) . . . . ?
N32 C54 C55 C56 179.0(7) . . . . ?
C52 C51 C56 F3B -173.3(9) . . . . ?
C50 C51 C56 F3B 4.6(13) . . . . ?
C52 C51 C56 C55 -0.9(12) . . . . ?
C50 C51 C56 C55 176.9(7) . . . . ?
C54 C55 C56 F3B 175.0(8) . . . . ?
C54 C55 C56 C51 2.0(12) . . . . ?
C61 N32 C57 C62 -5.8(9) . . . . ?
C54 N32 C57 C62 172.1(7) . . . . ?
C61 N32 C57 C58 -131.9(8) . . . . ?
C54 N32 C57 C58 45.9(11) . . . . ?
C61 N32 C57 C60 120.1(8) . . . . ?
C54 N32 C57 C60 -62.0(11) . . . . ?
N32 C57 C58 C59 -142.1(8) . . . . ?
C62 C57 C58 C59 97.4(8) . . . . ?
C60 C57 C58 C59 -17.8(6) . . . . ?
C57 C58 C59 C60 18.0(6) . . . . ?
C58 C59 C60 C57 -17.7(6) . . . . ?
N32 C57 C60 C59 142.7(8) . . . . ?
C62 C57 C60 C59 -97.3(8) . . . . ?
C58 C57 C60 C59 17.8(6) . . . . ?
C54 N32 C61 N33 -177.7(7) . . . . ?
C57 N32 C61 N33 0.2(9) . . . . ?
C54 N32 C61 S3 3.5(12) . . . . ?
C57 N32 C61 S3 -178.6(6) . . . . ?
C62 N33 C61 N32 6.3(9) . . . . ?
C64 N33 C61 N32 -174.2(7) . . . . ?
C62 N33 C61 S3 -174.9(6) . . . . ?
C64 N33 C61 S3 4.6(11) . . . . ?
C61 N33 C62 O32 171.0(8) . . . . ?
C64 N33 C62 O32 -8.6(13) . . . . ?
C61 N33 C62 C57 -9.8(9) . . . . ?
C64 N33 C62 C57 170.7(7) . . . . ?
N32 C57 C62 O32 -171.8(8) . . . . ?
C58 C57 C62 O32 -41.1(12) . . . . ?
C60 C57 C62 O32 58.3(12) . . . . ?
N32 C57 C62 N33 9.0(8) . . . . ?
C58 C57 C62 N33 139.7(7) . . . . ?
C60 C57 C62 N33 -120.9(7) . . . . ?
C67 N34 C63 C64 -2.5(12) . . . . ?
N34 C63 C64 C65 3.9(12) . . . . ?
N34 C63 C64 N33 -178.2(7) . . . . ?
C62 N33 C64 C63 -55.8(10) . . . . ?
C61 N33 C64 C63 124.7(8) . . . . ?
C62 N33 C64 C65 122.0(9) . . . . ?
C61 N33 C64 C65 -57.4(11) . . . . ?
C63 C64 C65 C66 -3.2(12) . . . . ?
N33 C64 C65 C66 179.0(7) . . . . ?
C64 C65 C66 C67 1.3(12) . . . . ?
C64 C65 C66 C68 -178.4(8) . . . . ?
C63 N34 C67 C66 0.5(12) . . . . ?
C63 N34 C67 C69 178.9(7) . . . . ?
C65 C66 C67 N34 0.0(12) . . . . ?
C68 C66 C67 N34 179.7(8) . . . . ?
C65 C66 C67 C69 -178.3(8) . . . . ?
C68 C66 C67 C69 1.5(12) . . . . ?
C65 C66 C68 F32 -119.2(9) . . . . ?
C67 C66 C68 F32 61.1(10) . . . . ?
C65 C66 C68 F33 120.2(9) . . . . ?
C67 C66 C68 F33 -59.5(11) . . . . ?
C65 C66 C68 F31 0.0(12) . . . . ?
C67 C66 C68 F31 -179.7(7) . . . . ?
C4 N41 C70 O41 -3.7(13) . . . . ?
C4 N41 C70 C71 175.2(8) . . . . ?
O41 C70 C71 C76 133.9(9) . . . . ?
N41 C70 C71 C76 -45.0(10) . . . . ?
O41 C70 C71 C72 -42.5(11) . . . . ?
N41 C70 C71 C72 138.6(8) . . . . ?
C76 C71 C72 F4A -178.0(8) . . . . ?
C70 C71 C72 F4A -1.4(12) . . . . ?
C76 C71 C72 C73 1.0(11) . . . . ?
C70 C71 C72 C73 177.7(7) . . . . ?
F4A C72 C73 C74 177.5(8) . . . . ?
C71 C72 C73 C74 -1.6(11) . . . . ?
C72 C73 C74 C75 1.8(11) . . . . ?
C72 C73 C74 N42 178.9(7) . . . . ?
C81 N42 C74 C73 98.8(9) . . . . ?
C77 N42 C74 C73 -84.5(9) . . . . ?
C81 N42 C74 C75 -84.0(9) . . . . ?
C77 N42 C74 C75 92.6(9) . . . . ?
C73 C74 C75 C76 -1.6(11) . . . . ?
N42 C74 C75 C76 -178.6(7) . . . . ?
C74 C75 C76 F4B -174.2(8) . . . . ?
C74 C75 C76 C71 1.0(12) . . . . ?
C72 C71 C76 C75 -0.8(12) . . . . ?
C70 C71 C76 C75 -177.2(7) . . . . ?
C72 C71 C76 F4B 174.3(8) . . . . ?
C70 C71 C76 F4B -2.2(13) . . . . ?
C81 N42 C77 C82 3.2(9) . . . . ?
C74 N42 C77 C82 -173.7(7) . . . . ?
C81 N42 C77 C80 -122.0(8) . . . . ?
C74 N42 C77 C80 61.1(10) . . . . ?
C81 N42 C77 C78 129.9(8) . . . . ?
C74 N42 C77 C78 -47.0(11) . . . . ?
N42 C77 C78 C79 142.2(7) . . . . ?
C82 C77 C78 C79 -96.6(7) . . . . ?
C80 C77 C78 C79 18.1(6) . . . . ?
C77 C78 C79 C80 -18.1(6) . . . . ?
N42 C77 C80 C79 -143.5(7) . . . . ?
C82 C77 C80 C79 97.0(7) . . . . ?
C78 C77 C80 C79 -18.2(6) . . . . ?
C78 C79 C80 C77 18.3(6) . . . . ?
C74 N42 C81 N43 177.8(7) . . . . ?
C77 N42 C81 N43 0.9(9) . . . . ?
C74 N42 C81 S4 -3.9(12) . . . . ?
C77 N42 C81 S4 179.1(6) . . . . ?
C82 N43 C81 N42 -5.1(9) . . . . ?
C84 N43 C81 N42 175.2(7) . . . . ?
C82 N43 C81 S4 176.7(6) . . . . ?
C84 N43 C81 S4 -3.1(12) . . . . ?
C81 N43 C82 O42 -172.3(8) . . . . ?
C84 N43 C82 O42 7.5(13) . . . . ?
C81 N43 C82 C77 7.1(9) . . . . ?
C84 N43 C82 C77 -173.1(7) . . . . ?
N42 C77 C82 O42 173.4(9) . . . . ?
C80 C77 C82 O42 -57.3(12) . . . . ?
C78 C77 C82 O42 42.0(12) . . . . ?
N42 C77 C82 N43 -5.9(8) . . . . ?
C80 C77 C82 N43 123.3(7) . . . . ?
C78 C77 C82 N43 -137.4(7) . . . . ?
C87 N44 C83 C84 -1.5(12) . . . . ?
N44 C83 C84 C85 -1.5(13) . . . . ?
N44 C83 C84 N43 178.7(7) . . . . ?
C81 N43 C84 C85 53.5(12) . . . . ?
C82 N43 C84 C85 -126.3(9) . . . . ?
C81 N43 C84 C83 -126.7(9) . . . . ?
C82 N43 C84 C83 53.6(11) . . . . ?
C83 C84 C85 C86 3.3(12) . . . . ?
N43 C84 C85 C86 -176.8(7) . . . . ?
C84 C85 C86 C87 -2.2(12) . . . . ?
C84 C85 C86 C88 177.4(8) . . . . ?
C83 N44 C87 C86 2.6(12) . . . . ?
C83 N44 C87 C89 -176.4(7) . . . . ?
C85 C86 C87 N44 -0.7(13) . . . . ?
C88 C86 C87 N44 179.6(8) . . . . ?
C85 C86 C87 C89 178.2(8) . . . . ?
C88 C86 C87 C89 -1.4(13) . . . . ?
C87 C86 C88 F43 -179.8(8) . . . . ?
C85 C86 C88 F43 0.5(11) . . . . ?
C87 C86 C88 F41 -58.8(11) . . . . ?
C85 C86 C88 F41 121.5(9) . . . . ?
C87 C86 C88 F42 59.4(11) . . . . ?
C85 C86 C88 F42 -120.3(8) . . . . ?
C91 N1 C5 O1 179.6(9) . . . . ?
C90 N1 C5 O1 -3.3(16) . . . . ?
C93 N2 C6 O2 -170.9(11) . . . . ?
C92 N2 C6 O2 -0.9(15) . . . . ?
C95 N3 C7 O3 173.9(10) . . . . ?
C94 N3 C7 O3 -0.4(16) . . . . ?
C96 N4 C8 O4 0.1(16) . . . . ?
C97 N4 C8 O4 178.7(9) . . . . ?

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
_geom_hbond_publ_flag
N11 H1 O31 0.86(9) 2.11(9) 2.921(10) 157(9) 3_575 yes
N21 H2 O41 0.75(9) 2.20(10) 2.930(10) 162(10) 3_465 yes
N31 H3 O11 0.96(9) 1.85(9) 2.772(10) 161(8) . yes
N41 H4 O21 0.79(9) 2.01(9) 2.791(10) 168(9) . yes

_refine_diff_density_max         0.596
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_KA1087_0m_APA-DMF-2-1
_database_code_depnum_ccdc_archive 'CCDC 2152151'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-02-15 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            Apalutamide-Dimethylformamaide-2:1
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C21 H15 F4 N5 O2 S), C3 H7 N O'
_chemical_formula_sum            'C45 H37 F8 N11 O5 S2'
_chemical_formula_weight         1027.97

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'
F F 0.0171 0.0103 '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                   12.3588(11)
_cell_length_b                   17.3486(15)
_cell_length_c                   23.177(2)
_cell_angle_alpha                68.252(5)
_cell_angle_beta                 81.670(5)
_cell_angle_gamma                89.735(5)
_cell_volume                     4560.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9864
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      29.77

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             2112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.210
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6521
_exptl_absorpt_correction_T_max  0.7833
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45004
_diffrn_reflns_av_unetI/netI     0.0940
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.147
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             45004
_reflns_number_gt                32486
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+25.5581P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         45004
_refine_ls_number_parameters     1352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0816
_refine_ls_wR_factor_ref         0.1932
_refine_ls_wR_factor_gt          0.1779
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_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
C1A C 0.7347(5) 0.3556(3) 0.1853(3) 0.0175(14) Uani 1 1 d . . . . .
C2A C 0.7235(5) 0.3403(3) 0.1326(3) 0.0199(15) Uani 1 1 d . . . . .
H2A H 0.655351 0.320487 0.127647 0.024 Uiso 1 1 calc R U . . .
C3A C 0.8150(6) 0.3547(4) 0.0865(3) 0.0208(15) Uani 1 1 d . . . . .
C4A C 0.9120(6) 0.3825(4) 0.0972(3) 0.0264(16) Uani 1 1 d . . . . .
C5A C 0.8353(6) 0.3825(4) 0.1927(4) 0.0329(18) Uani 1 1 d . . . . .
H5A H 0.841436 0.391892 0.229988 0.039 Uiso 1 1 calc R U . . .
C6A C 0.6024(5) 0.2685(3) 0.2789(3) 0.0181(14) Uani 1 1 d . . . . .
C7A C 0.4793(5) 0.3685(4) 0.2863(3) 0.0200(15) Uani 1 1 d . . . . .
C8A C 0.5693(5) 0.4066(4) 0.2318(3) 0.0199(15) Uani 1 1 d . . . . .
C9A C 0.8080(7) 0.3403(4) 0.0273(3) 0.0361(19) Uani 1 1 d . . . . .
C10A C 1.0117(7) 0.3986(4) 0.0503(4) 0.0363(19) Uani 1 1 d . . . . .
C11A C 0.4317(5) 0.2159(3) 0.3525(3) 0.0155(14) Uani 1 1 d . . . . .
C12A C 0.3591(5) 0.1813(3) 0.3278(3) 0.0196(15) Uani 1 1 d . . . . .
H12A H 0.360874 0.199037 0.283616 0.024 Uiso 1 1 calc R U . . .
C13A C 0.2843(5) 0.1204(3) 0.3688(3) 0.0223(15) Uani 1 1 d . . . . .
H131 H 0.234125 0.096269 0.352097 0.027 Uiso 0.434(9) 1 calc R U P A 2
C14A C 0.2786(5) 0.0925(3) 0.4332(3) 0.0146(14) Uani 1 1 d . . . . .
C15A C 0.3525(6) 0.1299(4) 0.4557(3) 0.0247(16) Uani 1 1 d . . . . .
H15A H 0.350121 0.112649 0.499908 0.030 Uiso 0.566(9) 1 calc R U P A 1
C16A C 0.4297(5) 0.1916(4) 0.4162(3) 0.0232(15) Uani 1 1 d . . . . .
H16A H 0.479628 0.216238 0.432643 0.028 Uiso 1 1 calc R U . . .
C17A C 0.3603(5) 0.3879(4) 0.2731(3) 0.0235(16) Uani 1 1 d . . . . .
H17A H 0.354477 0.412444 0.227815 0.028 Uiso 1 1 calc R U . A 1
H17B H 0.306920 0.340076 0.295390 0.028 Uiso 1 1 calc R U . A 1
C18A C 0.4633(6) 0.4122(4) 0.3343(3) 0.0268(17) Uani 1 1 d . . . . .
H18A H 0.522570 0.453954 0.328143 0.032 Uiso 1 1 calc R U . A 1
H18B H 0.447023 0.373598 0.378710 0.032 Uiso 1 1 calc R U . A 1
C19A C 0.3570(13) 0.4508(8) 0.3039(8) 0.022(4) Uani 0.566(9) 1 d . . P A 1
H19A H 0.290721 0.444368 0.335306 0.027 Uiso 0.566(9) 1 calc R U P A 1
H19B H 0.369423 0.509069 0.273727 0.027 Uiso 0.566(9) 1 calc R U P A 1
C19' C 0.3471(17) 0.4092(15) 0.3326(11) 0.037(5) Uani 0.434(9) 1 d . . P A 2
H19C H 0.314176 0.463233 0.326385 0.044 Uiso 0.434(9) 1 calc R U P A 2
H19D H 0.306175 0.364762 0.369899 0.044 Uiso 0.434(9) 1 calc R U P A 2
C20A C 0.2017(5) 0.0210(4) 0.4749(3) 0.0199(15) Uani 1 1 d . . . . .
C21A C 0.0631(5) -0.0364(4) 0.5691(3) 0.0248(16) Uani 1 1 d . . . . .
H21A H -0.002570 -0.011672 0.582372 0.037 Uiso 1 1 calc R U . . .
H21B H 0.097510 -0.067667 0.605805 0.037 Uiso 1 1 calc R U . . .
H21C H 0.042583 -0.074066 0.549199 0.037 Uiso 1 1 calc R U . . .
S1A S 0.66612(13) 0.18102(9) 0.29218(8) 0.0227(4) Uani 1 1 d . . . . .
F1A F 0.8708(4) 0.2803(2) 0.02149(19) 0.0431(11) Uani 1 1 d . . . . .
F2A F 0.7045(4) 0.3214(3) 0.02344(19) 0.0478(12) Uani 1 1 d . . . . .
F3A F 0.8406(4) 0.4098(2) -0.02349(18) 0.0446(12) Uani 1 1 d . . . . .
F4A F 0.2001(5) 0.0923(3) 0.3491(3) 0.026(2) Uani 0.566(9) 1 d . . P A 1
F5A F 0.3435(7) 0.1130(5) 0.5146(4) 0.031(3) Uani 0.434(9) 1 d . . P A 2
O1A O 0.5797(4) 0.4779(2) 0.1937(2) 0.0278(11) Uani 1 1 d . . . . .
O2A O 0.1978(3) -0.0428(2) 0.4629(2) 0.0258(11) Uani 1 1 d . . . . .
N1A N 0.9238(5) 0.3958(4) 0.1490(3) 0.0385(16) Uani 1 1 d . . . . .
N2A N 0.6424(4) 0.3450(3) 0.2336(2) 0.0171(12) Uani 1 1 d . . . . .
N3A N 0.5076(4) 0.2814(3) 0.3100(2) 0.0177(12) Uani 1 1 d . . . . .
N4A N 1.0875(6) 0.4113(4) 0.0133(3) 0.0505(19) Uani 1 1 d . . . . .
N5A N 0.1401(4) 0.0292(3) 0.5242(3) 0.0191(13) Uani 1 1 d . . . . .
H5NA H 0.133(5) 0.073(4) 0.528(3) 0.023 Uiso 1 1 d . U . . .
C1B C -0.2142(5) 0.6173(3) 0.1848(3) 0.0149(14) Uani 1 1 d . . . . .
C2B C -0.2986(5) 0.6430(3) 0.2196(3) 0.0140(14) Uani 1 1 d . . . . .
H2B H -0.292910 0.640975 0.260596 0.017 Uiso 1 1 calc R U . . .
C3B C -0.3907(5) 0.6714(3) 0.1922(3) 0.0163(14) Uani 1 1 d . . . . .
C4B C -0.3942(5) 0.6739(3) 0.1316(3) 0.0186(15) Uani 1 1 d . . . . .
C5B C -0.2233(5) 0.6243(4) 0.1244(3) 0.0217(15) Uani 1 1 d . . . . .
H5B H -0.163988 0.608425 0.100944 0.026 Uiso 1 1 calc R U . . .
C6B C -0.1177(5) 0.5202(3) 0.2686(3) 0.0136(13) Uani 1 1 d . . . . .
C7B C 0.0643(5) 0.5560(3) 0.2175(3) 0.0149(14) Uani 1 1 d . . . . .
C8B C -0.0122(5) 0.6136(4) 0.1779(3) 0.0175(14) Uani 1 1 d . . . . .
C9B C -0.4861(6) 0.6964(4) 0.2284(3) 0.0243(16) Uani 1 1 d . . . . .
C10B C -0.4904(6) 0.6988(4) 0.1011(3) 0.0233(16) Uani 1 1 d . . . . .
C11B C 0.0246(4) 0.4459(3) 0.3277(3) 0.0105(13) Uani 1 1 d . . . . .
C12B C 0.0437(5) 0.3651(3) 0.3306(3) 0.0168(14) Uani 1 1 d . . . . .
H12B H 0.031900 0.348792 0.297042 0.020 Uiso 1 1 calc R U . . .
C13B C 0.0799(5) 0.3099(3) 0.3830(3) 0.0162(14) Uani 1 1 d . . . . .
H132 H 0.090598 0.254480 0.385711 0.019 Uiso 0.408(9) 1 calc R U P B 2
C14B C 0.1013(5) 0.3317(3) 0.4317(3) 0.0147(14) Uani 1 1 d . . . . .
C15B C 0.0822(5) 0.4128(3) 0.4269(3) 0.0189(15) Uani 1 1 d . . . . .
H15B H 0.096039 0.429457 0.459978 0.023 Uiso 0.592(9) 1 calc R U P B 1
C16B C 0.0438(5) 0.4698(3) 0.3757(3) 0.0153(14) Uani 1 1 d . . . . .
H16B H 0.030837 0.524705 0.373603 0.018 Uiso 1 1 calc R U . . .
C17B C 0.1403(5) 0.5117(3) 0.1803(3) 0.0164(14) Uani 1 1 d . . . . .
H17C H 0.159936 0.455577 0.206685 0.020 Uiso 1 1 calc R U . . .
H17D H 0.113572 0.511232 0.142155 0.020 Uiso 1 1 calc R U . . .
C18B C 0.1667(5) 0.6020(3) 0.2223(3) 0.0172(14) Uani 1 1 d . . . . .
H18C H 0.195267 0.575666 0.262471 0.021 Uiso 1 1 calc R U . . .
H18D H 0.158700 0.662202 0.212167 0.021 Uiso 1 1 calc R U . . .
C19B C 0.2292(5) 0.5811(3) 0.1672(3) 0.0183(14) Uani 1 1 d . . . . .
H19E H 0.232560 0.626561 0.125545 0.022 Uiso 1 1 calc R U . . .
H19F H 0.302801 0.560253 0.174246 0.022 Uiso 1 1 calc R U . . .
C20B C 0.1401(5) 0.2686(3) 0.4887(3) 0.0169(14) Uani 1 1 d . . . . .
C21B C 0.2638(7) 0.2456(4) 0.5661(3) 0.037(2) Uani 1 1 d . . . . .
H21D H 0.343968 0.248114 0.557106 0.056 Uiso 1 1 calc R U . . .
H21E H 0.235745 0.187828 0.579719 0.056 Uiso 1 1 calc R U . . .
H21F H 0.240918 0.266663 0.599551 0.056 Uiso 1 1 calc R U . . .
S1B S -0.22450(13) 0.47202(9) 0.31989(7) 0.0183(4) Uani 1 1 d . . . . .
F1B F -0.5772(3) 0.6492(2) 0.23536(19) 0.0368(10) Uani 1 1 d . . . . .
F2B F -0.4692(3) 0.6890(2) 0.28494(18) 0.0336(10) Uani 1 1 d . . . . .
F3B F -0.5119(3) 0.7750(2) 0.19924(18) 0.0358(10) Uani 1 1 d . . . . .
F4B F 0.0920(5) 0.2310(3) 0.3854(3) 0.026(2) Uani 0.592(9) 1 d . . P B 1
F5B F 0.0829(7) 0.4381(5) 0.4754(4) 0.022(3) Uani 0.408(9) 1 d . . P B 2
O1B O 0.0092(4) 0.6714(3) 0.1297(2) 0.0255(11) Uani 1 1 d . . . . .
O2B O 0.0983(4) 0.1968(2) 0.5125(2) 0.0249(11) Uani 1 1 d . . . . .
N1B N -0.3110(4) 0.6521(3) 0.0977(2) 0.0191(12) Uani 1 1 d . . . . .
N2B N -0.1191(4) 0.5845(3) 0.2103(2) 0.0132(11) Uani 1 1 d . . . . .
N3B N -0.0110(4) 0.5047(3) 0.2729(2) 0.0134(11) Uani 1 1 d . . . . .
N4B N -0.5658(5) 0.7152(3) 0.0766(3) 0.0333(15) Uani 1 1 d . . . . .
N5B N 0.2206(5) 0.2961(3) 0.5097(3) 0.0245(14) Uani 1 1 d . . . . .
H5NB H 0.254(5) 0.350(4) 0.491(3) 0.021(17) Uiso 1 1 d . . . . .
C1C C 0.8774(5) 0.1038(3) 0.1782(3) 0.0161(14) Uani 1 1 d . . . . .
C2C C 0.9353(5) 0.1438(3) 0.2066(3) 0.0158(14) Uani 1 1 d . . . . .
H2C H 0.903585 0.151322 0.243875 0.019 Uiso 1 1 calc R U . . .
C3C C 1.0416(5) 0.1723(3) 0.1784(3) 0.0186(15) Uani 1 1 d . . . . .
C4C C 1.0824(5) 0.1598(4) 0.1237(3) 0.0207(15) Uani 1 1 d . . . . .
C5C C 0.9230(5) 0.0969(4) 0.1229(3) 0.0195(15) Uani 1 1 d . . . . .
H5C H 0.879587 0.071274 0.103633 0.023 Uiso 1 1 calc R U . . .
C6C C 0.7329(5) 0.0142(3) 0.2650(3) 0.0150(14) Uani 1 1 d . . . . .
C7C C 0.5805(5) 0.0443(3) 0.2118(3) 0.0133(13) Uani 1 1 d . . . . .
C8C C 0.6787(5) 0.0945(4) 0.1700(3) 0.0201(15) Uani 1 1 d . . . . .
C9C C 1.1108(6) 0.2140(4) 0.2074(4) 0.0295(17) Uani 1 1 d . . . . .
C10C C 1.1944(6) 0.1842(4) 0.0932(3) 0.0272(17) Uani 1 1 d . . . . .
C11C C 0.5597(5) -0.0582(3) 0.3252(3) 0.0111(13) Uani 1 1 d . . . . .
C12C C 0.5227(5) -0.0309(3) 0.3734(3) 0.0152(14) Uani 1 1 d . . . . .
H12C H 0.540585 0.024078 0.369814 0.018 Uiso 1 1 calc R U . . .
C13C C 0.4591(5) -0.0859(3) 0.4270(3) 0.0166(14) Uani 1 1 d . . . . .
H133 H 0.432991 -0.067096 0.459850 0.020 Uiso 0.477(9) 1 calc R U P C 2
C14C C 0.4315(5) -0.1670(3) 0.4351(3) 0.0143(14) Uani 1 1 d . . . . .
C15C C 0.4710(5) -0.1919(3) 0.3856(3) 0.0137(13) Uani 1 1 d . . . . .
H15C H 0.454403 -0.247189 0.389641 0.016 Uiso 0.523(9) 1 calc R U P C 1
C16C C 0.5333(5) -0.1391(3) 0.3312(3) 0.0164(14) Uani 1 1 d . . . D 1
H16C H 0.558070 -0.157585 0.298041 0.020 Uiso 1 1 calc R U . D 1
C17C C 0.4789(5) 0.0979(3) 0.2149(3) 0.0175(14) Uani 1 1 d . . . E 1
H17E H 0.429672 0.077028 0.255776 0.021 Uiso 1 1 calc R U . E 1
H17F H 0.497497 0.158102 0.201050 0.021 Uiso 1 1 calc R U . E 1
C18C C 0.5169(5) -0.0010(4) 0.1799(3) 0.0224(15) Uani 1 1 d . . . E 1
H18E H 0.480131 -0.054629 0.209202 0.027 Uiso 1 1 calc R U . E 1
H18F H 0.560228 -0.006947 0.142557 0.027 Uiso 1 1 calc R U . E 1
C19C C 0.4401(5) 0.0722(4) 0.1641(3) 0.0232(16) Uani 1 1 d . . . E 1
H19G H 0.459563 0.114060 0.120953 0.028 Uiso 1 1 calc R U . E 1
H19H H 0.361433 0.054447 0.173078 0.028 Uiso 1 1 calc R U . E 1
C20C C 0.3683(5) -0.2275(3) 0.4950(3) 0.0172(14) Uani 1 1 d . . . F 1
C21C C 0.2161(6) -0.2466(4) 0.5798(3) 0.040(2) Uani 1 1 d . . . G 1
H21G H 0.138435 -0.243768 0.575292 0.060 Uiso 1 1 calc R U . G 1
H21H H 0.229457 -0.223465 0.610946 0.060 Uiso 1 1 calc R U . G 1
H21I H 0.236106 -0.304737 0.593711 0.060 Uiso 1 1 calc R U . G 1
S1C S 0.81067(13) -0.02458(9) 0.31944(7) 0.0177(4) Uani 1 1 d . . . H 1
F1C F 1.2017(3) 0.1729(2) 0.2213(2) 0.0394(11) Uani 1 1 d . . . I 1
F2C F 1.0581(4) 0.2196(3) 0.2591(2) 0.0490(12) Uani 1 1 d . . . J 1
F3C F 1.1451(4) 0.2920(2) 0.1674(2) 0.0510(13) Uani 1 1 d . . . K 1
F4C F 0.4347(5) -0.0583(4) 0.4742(3) 0.019(2) Uani 0.523(9) 1 d . . P C 1
F5C F 0.4502(6) -0.2707(4) 0.3920(3) 0.021(2) Uani 0.477(9) 1 d . . P C 2
O1C O 0.6859(4) 0.1456(3) 0.1171(2) 0.0314(12) Uani 1 1 d . . . . .
O2C O 0.4014(4) -0.2984(2) 0.5194(2) 0.0261(11) Uani 1 1 d . . . . .
N1C N 1.0251(4) 0.1242(3) 0.0948(2) 0.0244(13) Uani 1 1 d . . . . .
N2C N 0.7661(4) 0.0712(3) 0.2039(2) 0.0145(11) Uani 1 1 d . . . . .
N3C N 0.6249(4) -0.0033(3) 0.2689(2) 0.0140(11) Uani 1 1 d . . . . .
N4C N 1.2829(5) 0.2032(4) 0.0695(3) 0.0430(17) Uani 1 1 d . . . . .
N5C N 0.2820(5) -0.1991(3) 0.5196(3) 0.0223(13) Uani 1 1 d . . . . .
H5NC H 0.253(5) -0.156(4) 0.502(3) 0.014(18) Uiso 1 1 d . . . . .
C1D C -0.0880(5) 0.8490(3) 0.2140(3) 0.0164(14) Uani 1 1 d . . . . .
C2D C -0.0522(5) 0.8615(3) 0.1527(3) 0.0190(14) Uani 1 1 d . . . . .
H2D H 0.024032 0.864278 0.137729 0.023 Uiso 1 1 calc R U . . .
C3D C -0.1267(5) 0.8699(3) 0.1129(3) 0.0184(15) Uani 1 1 d . . . . .
C4D C -0.2384(5) 0.8679(3) 0.1367(3) 0.0171(14) Uani 1 1 d . . . . .
C5D C -0.2012(5) 0.8451(4) 0.2350(3) 0.0197(15) Uani 1 1 d . . . . .
H5D H -0.225383 0.835409 0.278009 0.024 Uiso 1 1 calc R U . . .
C6D C 0.0014(5) 0.7635(3) 0.3039(3) 0.0170(14) Uani 1 1 d . . . . .
C7D C 0.1305(5) 0.8633(3) 0.3022(3) 0.0157(14) Uani 1 1 d . . . . .
C8D C 0.0673(5) 0.9007(4) 0.2493(3) 0.0178(14) Uani 1 1 d . . . . .
C9D C -0.0924(6) 0.8781(4) 0.0464(3) 0.0231(16) Uani 1 1 d . . . . .
C10D C -0.3228(6) 0.8790(4) 0.0975(3) 0.0202(15) Uani 1 1 d . . . . .
C11D C 0.1391(5) 0.7122(3) 0.3725(3) 0.0185(15) Uani 1 1 d . . . . .
C12D C 0.2161(5) 0.6710(3) 0.3459(3) 0.0176(14) Uani 1 1 d . . . . .
H12D H 0.230943 0.685391 0.301687 0.021 Uiso 1 1 calc R U . . .
C13D C 0.2697(5) 0.6090(3) 0.3857(3) 0.0220(16) Uani 1 1 d . . . . .
H134 H 0.319865 0.578885 0.368211 0.026 Uiso 0.397(9) 1 calc R U P L 2
C14D C 0.2541(5) 0.5884(3) 0.4497(3) 0.0190(15) Uani 1 1 d . . . . .
C15D C 0.1791(5) 0.6330(4) 0.4739(3) 0.0249(16) Uani 1 1 d . . . . .
H15F H 0.167184 0.620606 0.517873 0.030 Uiso 0.603(9) 1 calc R U P L 1
C16D C 0.1216(5) 0.6947(4) 0.4359(3) 0.0222(15) Uani 1 1 d . . . . .
H16D H 0.070773 0.724463 0.453322 0.027 Uiso 1 1 calc R U . . .
C17D C 0.2564(5) 0.8809(4) 0.2833(3) 0.0201(15) Uani 1 1 d . . . . .
H17G H 0.299557 0.835028 0.307300 0.024 Uiso 1 1 calc R U . . .
H17H H 0.281838 0.898998 0.237549 0.024 Uiso 1 1 calc R U . . .
C18D C 0.1312(5) 0.9158(3) 0.3434(3) 0.0200(15) Uani 1 1 d . . . . .
H18G H 0.130133 0.882286 0.388563 0.024 Uiso 1 1 calc R U . . .
H18H H 0.074138 0.957099 0.337268 0.024 Uiso 1 1 calc R U . . .
C19D C 0.2469(5) 0.9533(4) 0.3075(3) 0.0253(16) Uani 1 1 d . . . . .
H19I H 0.246324 1.008748 0.273844 0.030 Uiso 1 1 calc R U . . .
H19J H 0.300778 0.952992 0.335274 0.030 Uiso 1 1 calc R U . . .
C20D C 0.3128(5) 0.5166(4) 0.4903(3) 0.0244(16) Uani 1 1 d . . . . .
C21D C 0.4123(6) 0.4617(4) 0.5777(3) 0.0343(19) Uani 1 1 d . . . . .
H21J H 0.449718 0.428999 0.554973 0.052 Uiso 1 1 calc R U . . .
H21K H 0.358386 0.425679 0.612469 0.052 Uiso 1 1 calc R U . . .
H21L H 0.466151 0.485705 0.594321 0.052 Uiso 1 1 calc R U . . .
S1D S -0.07013(14) 0.67638(9) 0.32033(8) 0.0230(4) Uani 1 1 d . . . . .
F1D F -0.1418(3) 0.8186(2) 0.03413(16) 0.0284(9) Uani 1 1 d . . . . .
F2D F 0.0157(3) 0.8734(2) 0.03276(17) 0.0306(9) Uani 1 1 d . . . . .
F3D F -0.1187(3) 0.9516(2) 0.00562(17) 0.0296(9) Uani 1 1 d . . . . .
F4D F 0.3437(5) 0.5676(4) 0.3641(3) 0.032(2) Uani 0.603(9) 1 d . . P L 1
F5D F 0.1624(7) 0.6142(5) 0.5305(4) 0.026(3) Uani 0.397(9) 1 d . . P L 2
O1D O 0.0758(3) 0.9697(2) 0.2094(2) 0.0213(10) Uani 1 1 d . . . . .
O2D O 0.3177(5) 0.4518(3) 0.4802(3) 0.0555(18) Uani 1 1 d . . . . .
N1D N -0.2757(4) 0.8544(3) 0.1974(2) 0.0186(12) Uani 1 1 d . . . . .
N2D N -0.0133(4) 0.8393(3) 0.2567(2) 0.0139(11) Uani 1 1 d . . . . .
N3D N 0.0853(4) 0.7773(3) 0.3306(2) 0.0192(12) Uani 1 1 d . . . . .
N4D N -0.3889(5) 0.8908(3) 0.0657(3) 0.0283(14) Uani 1 1 d . . . . .
N5D N 0.3571(4) 0.5282(3) 0.5349(2) 0.0217(13) Uani 1 1 d . . . . .
H5ND H 0.370(5) 0.580(4) 0.535(3) 0.017(17) Uiso 1 1 d . . . . .
C22A C 0.4423(6) 0.3275(4) 0.1124(4) 0.0356(19) Uani 1 1 d . . . . .
H22A H 0.456729 0.282666 0.098697 0.043 Uiso 1 1 calc R U . . .
C23A C 0.3735(7) 0.4637(5) 0.0914(4) 0.049(2) Uani 1 1 d . . . . .
H23A H 0.382678 0.515784 0.054473 0.074 Uiso 1 1 calc R U . . .
H23B H 0.420105 0.467022 0.121292 0.074 Uiso 1 1 calc R U . . .
H23C H 0.296765 0.454713 0.111450 0.074 Uiso 1 1 calc R U . . .
C24A C 0.3782(7) 0.4003(5) 0.0115(3) 0.046(2) Uani 1 1 d . . . . .
H24A H 0.415047 0.450323 -0.021715 0.069 Uiso 1 1 calc R U . . .
H24B H 0.298829 0.403003 0.012256 0.069 Uiso 1 1 calc R U . . .
H24C H 0.402915 0.351073 0.003236 0.069 Uiso 1 1 calc R U . . .
O3A O 0.4601(4) 0.3169(3) 0.1648(2) 0.0329(12) Uani 1 1 d . . . . .
N6A N 0.4047(5) 0.3950(4) 0.0720(3) 0.0320(15) Uani 1 1 d . . . . .
C22B C 0.2302(5) 0.8186(4) 0.1233(3) 0.0242(16) Uani 1 1 d . . . . .
H22B H 0.214770 0.772058 0.113054 0.029 Uiso 1 1 calc R U . . .
C23B C 0.3125(7) 0.9574(4) 0.0898(3) 0.039(2) Uani 1 1 d . . . . .
H23D H 0.306835 1.007976 0.053116 0.058 Uiso 1 1 calc R U . . .
H23E H 0.388337 0.953115 0.097932 0.058 Uiso 1 1 calc R U . . .
H23F H 0.264349 0.959738 0.126527 0.058 Uiso 1 1 calc R U . . .
C24B C 0.3113(7) 0.8859(4) 0.0142(3) 0.039(2) Uani 1 1 d . . . . .
H24D H 0.277631 0.931994 -0.015573 0.059 Uiso 1 1 calc R U . . .
H24E H 0.286456 0.833285 0.012582 0.059 Uiso 1 1 calc R U . . .
H24F H 0.391171 0.893127 0.003049 0.059 Uiso 1 1 calc R U . . .
O3B O 0.2021(4) 0.8116(3) 0.1784(2) 0.0278(11) Uani 1 1 d . . . . .
N6B N 0.2796(5) 0.8848(3) 0.0774(2) 0.0251(13) Uani 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
C1A C2A 1.366(8) . ?
C1A C5A 1.386(9) . ?
C1A N2A 1.438(8) . ?
C2A C3A 1.392(9) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.383(9) . ?
C3A C9A 1.497(9) . ?
C4A N1A 1.332(9) . ?
C4A C10A 1.473(10) . ?
C5A N1A 1.335(9) . ?
C5A H5A 0.9500 . ?
C6A N3A 1.347(8) . ?
C6A N2A 1.390(7) . ?
C6A S1A 1.653(6) . ?
C7A N3A 1.464(7) . ?
C7A C8A 1.501(9) . ?
C7A C18A 1.551(9) . ?
C7A C17A 1.556(9) . ?
C8A O1A 1.219(7) . ?
C8A N2A 1.388(7) . ?
C9A F1A 1.331(8) . ?
C9A F2A 1.345(8) . ?
C9A F3A 1.349(7) . ?
C10A N4A 1.136(9) . ?
C11A C16A 1.372(8) . ?
C11A C12A 1.380(8) . ?
C11A N3A 1.433(7) . ?
C12A C13A 1.374(9) . ?
C12A H12A 0.9500 . ?
C13A F4A 1.356(8) . ?
C13A C14A 1.378(9) . ?
C13A H131 0.9500 . ?
C14A C15A 1.386(9) . ?
C14A C20A 1.495(8) . ?
C15A F5A 1.272(10) . ?
C15A C16A 1.388(9) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C17A C19A 1.506(16) . ?
C17A C19' 1.54(2) . ?
C17A H17A 0.9900 . ?
C17A H17B 0.9900 . ?
C18A C19' 1.44(2) . ?
C18A C19A 1.607(16) . ?
C18A H18A 0.9900 . ?
C18A H18B 0.9900 . ?
C19A H19A 0.9900 . ?
C19A H19B 0.9900 . ?
C19' H19C 0.9900 . ?
C19' H19D 0.9900 . ?
C20A O2A 1.238(7) . ?
C20A N5A 1.332(8) . ?
C21A N5A 1.460(8) . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
N5A H5NA 0.80(6) . ?
C1B C5B 1.380(8) . ?
C1B C2B 1.399(8) . ?
C1B N2B 1.414(7) . ?
C2B C3B 1.383(8) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.396(9) . ?
C3B C9B 1.502(9) . ?
C4B N1B 1.342(8) . ?
C4B C10B 1.453(9) . ?
C5B N1B 1.327(8) . ?
C5B H5B 0.9500 . ?
C6B N3B 1.355(7) . ?
C6B N2B 1.400(7) . ?
C6B S1B 1.635(6) . ?
C7B N3B 1.457(7) . ?
C7B C8B 1.516(8) . ?
C7B C18B 1.539(8) . ?
C7B C17B 1.570(8) . ?
C8B O1B 1.188(7) . ?
C8B N2B 1.414(8) . ?
C9B F2B 1.317(7) . ?
C9B F3B 1.340(7) . ?
C9B F1B 1.350(7) . ?
C10B N4B 1.142(8) . ?
C11B C16B 1.372(8) . ?
C11B C12B 1.399(7) . ?
C11B N3B 1.430(7) . ?
C12B C13B 1.372(8) . ?
C12B H12B 0.9500 . ?
C13B F4B 1.358(7) . ?
C13B C14B 1.376(8) . ?
C13B H132 0.9500 . ?
C14B C15B 1.392(8) . ?
C14B C20B 1.510(8) . ?
C15B F5B 1.349(10) . ?
C15B C16B 1.379(8) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
C17B C19B 1.548(8) . ?
C17B H17C 0.9900 . ?
C17B H17D 0.9900 . ?
C18B C19B 1.554(8) . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?
C19B H19E 0.9900 . ?
C19B H19F 0.9900 . ?
C20B O2B 1.239(7) . ?
C20B N5B 1.331(8) . ?
C21B N5B 1.453(8) . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
N5B H5NB 0.94(6) . ?
C1C C5C 1.371(8) . ?
C1C C2C 1.380(8) . ?
C1C N2C 1.444(7) . ?
C2C C3C 1.385(8) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.387(9) . ?
C3C C9C 1.496(9) . ?
C4C N1C 1.336(8) . ?
C4C C10C 1.447(9) . ?
C5C N1C 1.334(8) . ?
C5C H5C 0.9500 . ?
C6C N3C 1.353(7) . ?
C6C N2C 1.396(7) . ?
C6C S1C 1.639(6) . ?
C7C N3C 1.460(7) . ?
C7C C8C 1.488(8) . ?
C7C C18C 1.544(8) . ?
C7C C17C 1.568(8) . ?
C8C O1C 1.208(7) . ?
C8C N2C 1.398(8) . ?
C9C F2C 1.315(8) . ?
C9C F1C 1.343(8) . ?
C9C F3C 1.353(7) . ?
C10C N4C 1.141(8) . ?
C11C C12C 1.387(8) . ?
C11C C16C 1.394(8) . ?
C11C N3C 1.427(7) . ?
C12C C13C 1.384(8) . ?
C12C H12C 0.9500 . ?
C13C F4C 1.345(8) . ?
C13C C14C 1.386(8) . ?
C13C H133 0.9500 . ?
C14C C15C 1.393(8) . ?
C14C C20C 1.502(8) . ?
C15C F5C 1.343(8) . ?
C15C C16C 1.375(8) . ?
C15C H15C 0.9500 . ?
C16C H16C 0.9500 . ?
C17C C19C 1.539(9) . ?
C17C H17E 0.9900 . ?
C17C H17F 0.9900 . ?
C18C C19C 1.545(8) . ?
C18C H18E 0.9900 . ?
C18C H18F 0.9900 . ?
C19C H19G 0.9900 . ?
C19C H19H 0.9900 . ?
C20C O2C 1.244(6) . ?
C20C N5C 1.316(8) . ?
C21C N5C 1.454(8) . ?
C21C H21G 0.9800 . ?
C21C H21H 0.9800 . ?
C21C H21I 0.9800 . ?
N5C H5NC 0.82(6) . ?
C1D C2D 1.361(8) . ?
C1D C5D 1.406(9) . ?
C1D N2D 1.415(7) . ?
C2D C3D 1.365(8) . ?
C2D H2D 0.9500 . ?
C3D C4D 1.406(9) . ?
C3D C9D 1.493(9) . ?
C4D N1D 1.348(8) . ?
C4D C10D 1.447(9) . ?
C5D N1D 1.326(8) . ?
C5D H5D 0.9500 . ?
C6D N3D 1.347(8) . ?
C6D N2D 1.396(7) . ?
C6D S1D 1.643(6) . ?
C7D N3D 1.464(7) . ?
C7D C8D 1.489(9) . ?
C7D C18D 1.545(8) . ?
C7D C17D 1.554(8) . ?
C8D O1D 1.205(7) . ?
C8D N2D 1.407(7) . ?
C9D F2D 1.337(7) . ?
C9D F1D 1.338(7) . ?
C9D F3D 1.348(7) . ?
C10D N4D 1.146(8) . ?
C11D C16D 1.368(9) . ?
C11D C12D 1.396(8) . ?
C11D N3D 1.424(7) . ?
C12D C13D 1.371(8) . ?
C12D H12D 0.9500 . ?
C13D F4D 1.315(8) . ?
C13D C14D 1.375(9) . ?
C13D H134 0.9500 . ?
C14D C15D 1.392(9) . ?
C14D C20D 1.511(8) . ?
C15D F5D 1.215(10) . ?
C15D C16D 1.379(8) . ?
C15D H15F 0.9500 . ?
C16D H16D 0.9500 . ?
C17D C19D 1.550(8) . ?
C17D H17G 0.9900 . ?
C17D H17H 0.9900 . ?
C18D C19D 1.557(9) . ?
C18D H18G 0.9900 . ?
C18D H18H 0.9900 . ?
C19D H19I 0.9900 . ?
C19D H19J 0.9900 . ?
C20D O2D 1.231(7) . ?
C20D N5D 1.316(8) . ?
C21D N5D 1.456(8) . ?
C21D H21J 0.9800 . ?
C21D H21K 0.9800 . ?
C21D H21L 0.9800 . ?
N5D H5ND 0.92(6) . ?
C22A O3A 1.212(8) . ?
C22A N6A 1.332(8) . ?
C22A H22A 0.9500 . ?
C23A N6A 1.455(9) . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C24A N6A 1.456(9) . ?
C24A H24A 0.9800 . ?
C24A H24B 0.9800 . ?
C24A H24C 0.9800 . ?
C22B O3B 1.233(7) . ?
C22B N6B 1.318(8) . ?
C22B H22B 0.9500 . ?
C23B N6B 1.463(8) . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
C24B N6B 1.452(8) . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 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
C2A C1A C5A 120.4(6) . . ?
C2A C1A N2A 120.8(6) . . ?
C5A C1A N2A 118.8(6) . . ?
C1A C2A C3A 118.1(6) . . ?
C1A C2A H2A 120.9 . . ?
C3A C2A H2A 120.9 . . ?
C4A C3A C2A 117.9(6) . . ?
C4A C3A C9A 121.3(6) . . ?
C2A C3A C9A 120.8(6) . . ?
N1A C4A C3A 124.2(6) . . ?
N1A C4A C10A 115.3(6) . . ?
C3A C4A C10A 120.5(7) . . ?
N1A C5A C1A 122.0(7) . . ?
N1A C5A H5A 119.0 . . ?
C1A C5A H5A 119.0 . . ?
N3A C6A N2A 107.0(5) . . ?
N3A C6A S1A 128.3(5) . . ?
N2A C6A S1A 124.6(5) . . ?
N3A C7A C8A 101.6(5) . . ?
N3A C7A C18A 117.0(5) . . ?
C8A C7A C18A 115.1(5) . . ?
N3A C7A C17A 118.1(5) . . ?
C8A C7A C17A 116.5(5) . . ?
C18A C7A C17A 89.4(5) . . ?
O1A C8A N2A 125.5(6) . . ?
O1A C8A C7A 127.9(6) . . ?
N2A C8A C7A 106.6(5) . . ?
F1A C9A F2A 108.6(6) . . ?
F1A C9A F3A 107.1(6) . . ?
F2A C9A F3A 105.9(6) . . ?
F1A C9A C3A 112.6(6) . . ?
F2A C9A C3A 111.7(6) . . ?
F3A C9A C3A 110.5(6) . . ?
N4A C10A C4A 178.8(8) . . ?
C16A C11A C12A 121.8(6) . . ?
C16A C11A N3A 119.9(6) . . ?
C12A C11A N3A 118.3(5) . . ?
C13A C12A C11A 118.0(6) . . ?
C13A C12A H12A 121.0 . . ?
C11A C12A H12A 121.0 . . ?
F4A C13A C12A 121.5(6) . . ?
F4A C13A C14A 114.7(6) . . ?
C12A C13A C14A 123.1(6) . . ?
C12A C13A H131 118.4 . . ?
C14A C13A H131 118.4 . . ?
C13A C14A C15A 116.6(6) . . ?
C13A C14A C20A 120.2(6) . . ?
C15A C14A C20A 123.0(6) . . ?
F5A C15A C14A 119.3(7) . . ?
F5A C15A C16A 118.0(7) . . ?
C14A C15A C16A 122.4(6) . . ?
C14A C15A H15A 118.8 . . ?
C16A C15A H15A 118.8 . . ?
C11A C16A C15A 118.1(6) . . ?
C11A C16A H16A 121.0 . . ?
C15A C16A H16A 121.0 . . ?
C19A C17A C7A 90.4(7) . . ?
C19' C17A C7A 84.8(9) . . ?
C19A C17A H17A 113.6 . . ?
C7A C17A H17A 113.6 . . ?
C19A C17A H17B 113.6 . . ?
C7A C17A H17B 113.6 . . ?
H17A C17A H17B 110.8 . . ?
C19' C18A C7A 88.3(10) . . ?
C7A C18A C19A 87.0(7) . . ?
C7A C18A H18A 114.2 . . ?
C19A C18A H18A 114.2 . . ?
C7A C18A H18B 114.2 . . ?
C19A C18A H18B 114.2 . . ?
H18A C18A H18B 111.3 . . ?
C17A C19A C18A 89.1(8) . . ?
C17A C19A H19A 113.8 . . ?
C18A C19A H19A 113.8 . . ?
C17A C19A H19B 113.8 . . ?
C18A C19A H19B 113.8 . . ?
H19A C19A H19B 111.0 . . ?
C18A C19' C17A 94.1(13) . . ?
C18A C19' H19C 112.9 . . ?
C17A C19' H19C 112.9 . . ?
C18A C19' H19D 112.9 . . ?
C17A C19' H19D 112.9 . . ?
H19C C19' H19D 110.3 . . ?
O2A C20A N5A 122.9(6) . . ?
O2A C20A C14A 119.7(6) . . ?
N5A C20A C14A 117.4(5) . . ?
N5A C21A H21A 109.5 . . ?
N5A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
N5A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C4A N1A C5A 117.4(6) . . ?
C8A N2A C6A 111.6(5) . . ?
C8A N2A C1A 123.1(5) . . ?
C6A N2A C1A 123.9(5) . . ?
C6A N3A C11A 123.8(5) . . ?
C6A N3A C7A 112.6(5) . . ?
C11A N3A C7A 122.5(5) . . ?
C20A N5A C21A 122.9(5) . . ?
C20A N5A H5NA 123(5) . . ?
C21A N5A H5NA 113(5) . . ?
C5B C1B C2B 119.6(6) . . ?
C5B C1B N2B 119.3(6) . . ?
C2B C1B N2B 121.1(5) . . ?
C3B C2B C1B 117.6(6) . . ?
C3B C2B H2B 121.2 . . ?
C1B C2B H2B 121.2 . . ?
C2B C3B C4B 118.8(6) . . ?
C2B C3B C9B 120.1(6) . . ?
C4B C3B C9B 121.1(6) . . ?
N1B C4B C3B 123.1(6) . . ?
N1B C4B C10B 114.9(6) . . ?
C3B C4B C10B 122.0(6) . . ?
N1B C5B C1B 123.0(6) . . ?
N1B C5B H5B 118.5 . . ?
C1B C5B H5B 118.5 . . ?
N3B C6B N2B 106.3(5) . . ?
N3B C6B S1B 127.3(4) . . ?
N2B C6B S1B 126.4(5) . . ?
N3B C7B C8B 102.1(5) . . ?
N3B C7B C18B 122.0(5) . . ?
C8B C7B C18B 113.0(5) . . ?
N3B C7B C17B 118.5(4) . . ?
C8B C7B C17B 112.8(5) . . ?
C18B C7B C17B 88.8(4) . . ?
O1B C8B N2B 125.3(6) . . ?
O1B C8B C7B 129.1(6) . . ?
N2B C8B C7B 105.5(5) . . ?
F2B C9B F3B 106.8(5) . . ?
F2B C9B F1B 107.4(5) . . ?
F3B C9B F1B 105.6(5) . . ?
F2B C9B C3B 112.9(5) . . ?
F3B C9B C3B 112.9(5) . . ?
F1B C9B C3B 110.8(5) . . ?
N4B C10B C4B 177.1(7) . . ?
C16B C11B C12B 120.7(5) . . ?
C16B C11B N3B 120.0(5) . . ?
C12B C11B N3B 119.3(5) . . ?
C13B C12B C11B 118.5(6) . . ?
C13B C12B H12B 120.7 . . ?
C11B C12B H12B 120.8 . . ?
F4B C13B C12B 116.7(6) . . ?
F4B C13B C14B 120.7(6) . . ?
C12B C13B C14B 122.6(5) . . ?
C12B C13B H132 118.7 . . ?
C14B C13B H132 118.7 . . ?
C13B C14B C15B 117.2(5) . . ?
C13B C14B C20B 120.7(5) . . ?
C15B C14B C20B 122.1(6) . . ?
F5B C15B C16B 114.3(6) . . ?
F5B C15B C14B 122.8(6) . . ?
C16B C15B C14B 122.1(6) . . ?
C16B C15B H15B 118.9 . . ?
C14B C15B H15B 118.9 . . ?
C11B C16B C15B 118.9(5) . . ?
C11B C16B H16B 120.5 . . ?
C15B C16B H16B 120.5 . . ?
C19B C17B C7B 87.5(4) . . ?
C19B C17B H17C 114.1 . . ?
C7B C17B H17C 114.1 . . ?
C19B C17B H17D 114.1 . . ?
C7B C17B H17D 114.1 . . ?
H17C C17B H17D 111.2 . . ?
C7B C18B C19B 88.4(5) . . ?
C7B C18B H18C 113.9 . . ?
C19B C18B H18C 113.9 . . ?
C7B C18B H18D 113.9 . . ?
C19B C18B H18D 113.9 . . ?
H18C C18B H18D 111.1 . . ?
C17B C19B C18B 89.1(4) . . ?
C17B C19B H19E 113.8 . . ?
C18B C19B H19E 113.8 . . ?
C17B C19B H19F 113.8 . . ?
C18B C19B H19F 113.8 . . ?
H19E C19B H19F 111.0 . . ?
O2B C20B N5B 124.3(6) . . ?
O2B C20B C14B 120.6(6) . . ?
N5B C20B C14B 115.1(5) . . ?
N5B C21B H21D 109.5 . . ?
N5B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
N5B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C5B N1B C4B 117.8(5) . . ?
C6B N2B C1B 125.5(5) . . ?
C6B N2B C8B 112.1(5) . . ?
C1B N2B C8B 122.5(5) . . ?
C6B N3B C11B 123.2(5) . . ?
C6B N3B C7B 113.6(4) . . ?
C11B N3B C7B 123.1(5) . . ?
C20B N5B C21B 122.7(5) . . ?
C20B N5B H5NB 125(4) . . ?
C21B N5B H5NB 112(4) . . ?
C5C C1C C2C 120.5(6) . . ?
C5C C1C N2C 117.8(5) . . ?
C2C C1C N2C 121.6(5) . . ?
C1C C2C C3C 117.1(6) . . ?
C1C C2C H2C 121.5 . . ?
C3C C2C H2C 121.5 . . ?
C2C C3C C4C 118.4(6) . . ?
C2C C3C C9C 120.2(6) . . ?
C4C C3C C9C 121.3(6) . . ?
N1C C4C C3C 124.6(6) . . ?
N1C C4C C10C 113.7(6) . . ?
C3C C4C C10C 121.7(6) . . ?
N1C C5C C1C 123.4(6) . . ?
N1C C5C H5C 118.3 . . ?
C1C C5C H5C 118.3 . . ?
N3C C6C N2C 105.8(5) . . ?
N3C C6C S1C 127.7(5) . . ?
N2C C6C S1C 126.5(4) . . ?
N3C C7C C8C 102.2(5) . . ?
N3C C7C C18C 120.1(5) . . ?
C8C C7C C18C 113.2(5) . . ?
N3C C7C C17C 120.3(5) . . ?
C8C C7C C17C 112.8(4) . . ?
C18C C7C C17C 88.6(4) . . ?
O1C C8C N2C 124.7(6) . . ?
O1C C8C C7C 129.0(6) . . ?
N2C C8C C7C 106.4(5) . . ?
F2C C9C F1C 108.2(6) . . ?
F2C C9C F3C 107.4(5) . . ?
F1C C9C F3C 106.2(5) . . ?
F2C C9C C3C 112.4(6) . . ?
F1C C9C C3C 111.0(5) . . ?
F3C C9C C3C 111.4(6) . . ?
N4C C10C C4C 179.4(8) . . ?
C12C C11C C16C 120.3(5) . . ?
C12C C11C N3C 120.1(5) . . ?
C16C C11C N3C 119.6(5) . . ?
C13C C12C C11C 118.2(5) . . ?
C13C C12C H12C 120.9 . . ?
C11C C12C H12C 120.9 . . ?
F4C C13C C12C 115.2(6) . . ?
F4C C13C C14C 121.1(6) . . ?
C12C C13C C14C 123.3(6) . . ?
C12C C13C H133 118.3 . . ?
C14C C13C H133 118.3 . . ?
C13C C14C C15C 116.4(5) . . ?
C13C C14C C20C 122.7(6) . . ?
C15C C14C C20C 120.8(5) . . ?
F5C C15C C14C 118.9(6) . . ?
C16C C15C C14C 122.3(5) . . ?
C16C C15C H15C 118.9 . . ?
C14C C15C H15C 118.9 . . ?
C15C C16C C11C 119.4(6) . . ?
C15C C16C H16C 120.3 . . ?
C11C C16C H16C 120.3 . . ?
C19C C17C C7C 87.5(4) . . ?
C19C C17C H17E 114.1 . . ?
C7C C17C H17E 114.1 . . ?
C19C C17C H17F 114.1 . . ?
C7C C17C H17F 114.1 . . ?
H17E C17C H17F 111.2 . . ?
C7C C18C C19C 88.2(4) . . ?
C7C C18C H18E 114.0 . . ?
C19C C18C H18E 114.0 . . ?
C7C C18C H18F 114.0 . . ?
C19C C18C H18F 114.0 . . ?
H18E C18C H18F 111.2 . . ?
C17C C19C C18C 89.7(5) . . ?
C17C C19C H19G 113.7 . . ?
C18C C19C H19G 113.7 . . ?
C17C C19C H19H 113.7 . . ?
C18C C19C H19H 113.7 . . ?
H19G C19C H19H 111.0 . . ?
O2C C20C N5C 124.4(6) . . ?
O2C C20C C14C 119.6(6) . . ?
N5C C20C C14C 115.9(5) . . ?
N5C C21C H21G 109.5 . . ?
N5C C21C H21H 109.5 . . ?
H21G C21C H21H 109.5 . . ?
N5C C21C H21I 109.5 . . ?
H21G C21C H21I 109.5 . . ?
H21H C21C H21I 109.5 . . ?
C5C N1C C4C 115.9(5) . . ?
C6C N2C C8C 112.3(5) . . ?
C6C N2C C1C 124.5(5) . . ?
C8C N2C C1C 123.2(5) . . ?
C6C N3C C11C 122.9(5) . . ?
C6C N3C C7C 113.3(5) . . ?
C11C N3C C7C 123.6(5) . . ?
C20C N5C C21C 123.6(6) . . ?
C20C N5C H5NC 126(4) . . ?
C21C N5C H5NC 110(4) . . ?
C2D C1D C5D 119.2(6) . . ?
C2D C1D N2D 121.0(6) . . ?
C5D C1D N2D 119.8(6) . . ?
C1D C2D C3D 119.4(6) . . ?
C1D C2D H2D 120.3 . . ?
C3D C2D H2D 120.3 . . ?
C2D C3D C4D 118.3(6) . . ?
C2D C3D C9D 121.6(6) . . ?
C4D C3D C9D 120.0(6) . . ?
N1D C4D C3D 123.2(6) . . ?
N1D C4D C10D 114.7(5) . . ?
C3D C4D C10D 122.1(6) . . ?
N1D C5D C1D 123.0(6) . . ?
N1D C5D H5D 118.5 . . ?
C1D C5D H5D 118.5 . . ?
N3D C6D N2D 106.1(5) . . ?
N3D C6D S1D 128.8(5) . . ?
N2D C6D S1D 125.1(5) . . ?
N3D C7D C8D 102.6(5) . . ?
N3D C7D C18D 119.7(5) . . ?
C8D C7D C18D 112.5(5) . . ?
N3D C7D C17D 119.6(5) . . ?
C8D C7D C17D 114.2(5) . . ?
C18D C7D C17D 88.7(4) . . ?
O1D C8D N2D 124.7(6) . . ?
O1D C8D C7D 129.7(6) . . ?
N2D C8D C7D 105.5(5) . . ?
F2D C9D F1D 107.8(5) . . ?
F2D C9D F3D 106.8(5) . . ?
F1D C9D F3D 107.0(5) . . ?
F2D C9D C3D 112.2(6) . . ?
F1D C9D C3D 111.2(5) . . ?
F3D C9D C3D 111.5(5) . . ?
N4D C10D C4D 177.5(6) . . ?
C16D C11D C12D 121.4(6) . . ?
C16D C11D N3D 121.3(6) . . ?
C12D C11D N3D 117.2(6) . . ?
C13D C12D C11D 117.8(6) . . ?
C13D C12D H12D 121.1 . . ?
C11D C12D H12D 121.1 . . ?
F4D C13D C12D 121.3(6) . . ?
F4D C13D C14D 115.6(6) . . ?
C12D C13D C14D 123.0(6) . . ?
C12D C13D H134 118.5 . . ?
C14D C13D H134 118.5 . . ?
C13D C14D C15D 117.1(6) . . ?
C13D C14D C20D 119.5(6) . . ?
C15D C14D C20D 123.4(6) . . ?
F5D C15D C16D 120.1(7) . . ?
F5D C15D C14D 117.9(7) . . ?
C16D C15D C14D 122.0(7) . . ?
C16D C15D H15F 119.0 . . ?
C14D C15D H15F 119.0 . . ?
C11D C16D C15D 118.7(6) . . ?
C11D C16D H16D 120.7 . . ?
C15D C16D H16D 120.7 . . ?
C19D C17D C7D 89.0(5) . . ?
C19D C17D H17G 113.8 . . ?
C7D C17D H17G 113.8 . . ?
C19D C17D H17H 113.8 . . ?
C7D C17D H17H 113.8 . . ?
H17G C17D H17H 111.0 . . ?
C7D C18D C19D 89.1(5) . . ?
C7D C18D H18G 113.8 . . ?
C19D C18D H18G 113.8 . . ?
C7D C18D H18H 113.8 . . ?
C19D C18D H18H 113.8 . . ?
H18G C18D H18H 111.0 . . ?
C17D C19D C18D 88.4(5) . . ?
C17D C19D H19I 113.9 . . ?
C18D C19D H19I 113.9 . . ?
C17D C19D H19J 113.9 . . ?
C18D C19D H19J 113.9 . . ?
H19I C19D H19J 111.1 . . ?
O2D C20D N5D 123.6(6) . . ?
O2D C20D C14D 119.7(6) . . ?
N5D C20D C14D 116.7(6) . . ?
N5D C21D H21J 109.5 . . ?
N5D C21D H21K 109.5 . . ?
H21J C21D H21K 109.5 . . ?
N5D C21D H21L 109.5 . . ?
H21J C21D H21L 109.5 . . ?
H21K C21D H21L 109.5 . . ?
C5D N1D C4D 116.9(5) . . ?
C6D N2D C8D 112.3(5) . . ?
C6D N2D C1D 123.4(5) . . ?
C8D N2D C1D 123.4(5) . . ?
C6D N3D C11D 123.2(5) . . ?
C6D N3D C7D 113.0(5) . . ?
C11D N3D C7D 122.6(5) . . ?
C20D N5D C21D 120.7(6) . . ?
C20D N5D H5ND 122(4) . . ?
C21D N5D H5ND 115(4) . . ?
O3A C22A N6A 127.2(7) . . ?
O3A C22A H22A 116.4 . . ?
N6A C22A H22A 116.4 . . ?
N6A C23A H23A 109.5 . . ?
N6A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
N6A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
N6A C24A H24A 109.5 . . ?
N6A C24A H24B 109.5 . . ?
H24A C24A H24B 109.5 . . ?
N6A C24A H24C 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
C22A N6A C23A 119.5(6) . . ?
C22A N6A C24A 123.5(6) . . ?
C23A N6A C24A 116.5(6) . . ?
O3B C22B N6B 126.0(6) . . ?
O3B C22B H22B 117.0 . . ?
N6B C22B H22B 117.0 . . ?
N6B C23B H23D 109.5 . . ?
N6B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
N6B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
N6B C24B H24D 109.5 . . ?
N6B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
N6B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
C22B N6B C24B 121.5(6) . . ?
C22B N6B C23B 120.6(6) . . ?
C24B N6B C23B 117.7(6) . . ?

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
C5A C1A C2A C3A -1.6(9) . . . . ?
N2A C1A C2A C3A 177.7(5) . . . . ?
C1A C2A C3A C4A 0.9(9) . . . . ?
C1A C2A C3A C9A -179.2(6) . . . . ?
C2A C3A C4A N1A 0.5(10) . . . . ?
C9A C3A C4A N1A -179.4(6) . . . . ?
C2A C3A C4A C10A 179.8(6) . . . . ?
C9A C3A C4A C10A -0.1(10) . . . . ?
C2A C1A C5A N1A 1.1(10) . . . . ?
N2A C1A C5A N1A -178.3(6) . . . . ?
N3A C7A C8A O1A 175.1(6) . . . . ?
C18A C7A C8A O1A -57.4(9) . . . . ?
C17A C7A C8A O1A 45.4(9) . . . . ?
N3A C7A C8A N2A -6.5(6) . . . . ?
C18A C7A C8A N2A 121.0(6) . . . . ?
C17A C7A C8A N2A -136.3(5) . . . . ?
C4A C3A C9A F1A 63.6(8) . . . . ?
C2A C3A C9A F1A -116.3(7) . . . . ?
C4A C3A C9A F2A -173.8(6) . . . . ?
C2A C3A C9A F2A 6.2(9) . . . . ?
C4A C3A C9A F3A -56.1(9) . . . . ?
C2A C3A C9A F3A 123.9(7) . . . . ?
C16A C11A C12A C13A -0.7(9) . . . . ?
N3A C11A C12A C13A -178.0(5) . . . . ?
C11A C12A C13A F4A 169.8(6) . . . . ?
C11A C12A C13A C14A 0.0(9) . . . . ?
F4A C13A C14A C15A -169.7(6) . . . . ?
C12A C13A C14A C15A 0.7(9) . . . . ?
F4A C13A C14A C20A 14.9(8) . . . . ?
C12A C13A C14A C20A -174.7(6) . . . . ?
C13A C14A C15A F5A 172.6(7) . . . . ?
C20A C14A C15A F5A -12.1(10) . . . . ?
C13A C14A C15A C16A -0.8(9) . . . . ?
C20A C14A C15A C16A 174.4(6) . . . . ?
C12A C11A C16A C15A 0.6(9) . . . . ?
N3A C11A C16A C15A 177.9(5) . . . . ?
F5A C15A C16A C11A -173.3(7) . . . . ?
C14A C15A C16A C11A 0.2(10) . . . . ?
N3A C7A C17A C19A 136.4(8) . . . . ?
C8A C7A C17A C19A -102.2(8) . . . . ?
C18A C7A C17A C19A 15.8(7) . . . . ?
N3A C7A C17A C19' 107.4(11) . . . . ?
C8A C7A C17A C19' -131.2(10) . . . . ?
C18A C7A C17A C19' -13.2(10) . . . . ?
N3A C7A C18A C19' -107.5(11) . . . . ?
C8A C7A C18A C19' 133.2(11) . . . . ?
C17A C7A C18A C19' 14.0(11) . . . . ?
N3A C7A C18A C19A -136.3(7) . . . . ?
C8A C7A C18A C19A 104.4(7) . . . . ?
C17A C7A C18A C19A -14.8(7) . . . . ?
C7A C17A C19A C18A -15.2(7) . . . . ?
C7A C18A C19A C17A 15.3(7) . . . . ?
C7A C18A C19' C17A -14.2(10) . . . . ?
C7A C17A C19' C18A 14.2(10) . . . . ?
C13A C14A C20A O2A 47.2(8) . . . . ?
C15A C14A C20A O2A -127.9(7) . . . . ?
C13A C14A C20A N5A -133.2(6) . . . . ?
C15A C14A C20A N5A 51.7(8) . . . . ?
C3A C4A N1A C5A -1.1(10) . . . . ?
C10A C4A N1A C5A 179.5(6) . . . . ?
C1A C5A N1A C4A 0.3(10) . . . . ?
O1A C8A N2A C6A -174.4(6) . . . . ?
C7A C8A N2A C6A 7.2(7) . . . . ?
O1A C8A N2A C1A -7.5(10) . . . . ?
C7A C8A N2A C1A 174.1(5) . . . . ?
N3A C6A N2A C8A -4.7(7) . . . . ?
S1A C6A N2A C8A 177.9(5) . . . . ?
N3A C6A N2A C1A -171.5(5) . . . . ?
S1A C6A N2A C1A 11.2(8) . . . . ?
C2A C1A N2A C8A -85.7(7) . . . . ?
C5A C1A N2A C8A 93.6(7) . . . . ?
C2A C1A N2A C6A 79.6(8) . . . . ?
C5A C1A N2A C6A -101.1(7) . . . . ?
N2A C6A N3A C11A 168.4(5) . . . . ?
S1A C6A N3A C11A -14.4(9) . . . . ?
N2A C6A N3A C7A 0.1(7) . . . . ?
S1A C6A N3A C7A 177.3(5) . . . . ?
C16A C11A N3A C6A 100.6(7) . . . . ?
C12A C11A N3A C6A -82.1(8) . . . . ?
C16A C11A N3A C7A -92.3(7) . . . . ?
C12A C11A N3A C7A 85.1(7) . . . . ?
C8A C7A N3A C6A 4.0(7) . . . . ?
C18A C7A N3A C6A -122.3(6) . . . . ?
C17A C7A N3A C6A 132.8(6) . . . . ?
C8A C7A N3A C11A -164.4(5) . . . . ?
C18A C7A N3A C11A 69.3(8) . . . . ?
C17A C7A N3A C11A -35.7(8) . . . . ?
O2A C20A N5A C21A 0.7(10) . . . . ?
C14A C20A N5A C21A -178.9(5) . . . . ?
C5B C1B C2B C3B 2.7(8) . . . . ?
N2B C1B C2B C3B -177.6(5) . . . . ?
C1B C2B C3B C4B -0.7(8) . . . . ?
C1B C2B C3B C9B 177.3(5) . . . . ?
C2B C3B C4B N1B -1.9(8) . . . . ?
C9B C3B C4B N1B -179.9(5) . . . . ?
C2B C3B C4B C10B 176.6(5) . . . . ?
C9B C3B C4B C10B -1.4(8) . . . . ?
C2B C1B C5B N1B -2.3(9) . . . . ?
N2B C1B C5B N1B 178.1(5) . . . . ?
N3B C7B C8B O1B 174.1(6) . . . . ?
C18B C7B C8B O1B 41.2(9) . . . . ?
C17B C7B C8B O1B -57.7(8) . . . . ?
N3B C7B C8B N2B -5.9(6) . . . . ?
C18B C7B C8B N2B -138.8(5) . . . . ?
C17B C7B C8B N2B 122.3(5) . . . . ?
C2B C3B C9B F2B 1.1(8) . . . . ?
C4B C3B C9B F2B 179.1(5) . . . . ?
C2B C3B C9B F3B 122.3(6) . . . . ?
C4B C3B C9B F3B -59.6(7) . . . . ?
C2B C3B C9B F1B -119.5(6) . . . . ?
C4B C3B C9B F1B 58.5(7) . . . . ?
C16B C11B C12B C13B 1.3(8) . . . . ?
N3B C11B C12B C13B 178.8(5) . . . . ?
C11B C12B C13B F4B 176.7(6) . . . . ?
C11B C12B C13B C14B -2.1(9) . . . . ?
F4B C13B C14B C15B -177.2(6) . . . . ?
C12B C13B C14B C15B 1.5(9) . . . . ?
F4B C13B C14B C20B 0.7(9) . . . . ?
C12B C13B C14B C20B 179.5(6) . . . . ?
C13B C14B C15B F5B 169.0(7) . . . . ?
C20B C14B C15B F5B -8.8(10) . . . . ?
C13B C14B C15B C16B -0.2(9) . . . . ?
C20B C14B C15B C16B -178.1(6) . . . . ?
C12B C11B C16B C15B -0.1(9) . . . . ?
N3B C11B C16B C15B -177.5(5) . . . . ?
F5B C15B C16B C11B -170.6(6) . . . . ?
C14B C15B C16B C11B -0.5(9) . . . . ?
N3B C7B C17B C19B -144.9(5) . . . . ?
C8B C7B C17B C19B 95.9(5) . . . . ?
C18B C7B C17B C19B -18.6(4) . . . . ?
N3B C7B C18B C19B 141.9(5) . . . . ?
C8B C7B C18B C19B -95.8(5) . . . . ?
C17B C7B C18B C19B 18.5(4) . . . . ?
C7B C17B C19B C18B 18.5(4) . . . . ?
C7B C18B C19B C17B -18.8(4) . . . . ?
C13B C14B C20B O2B -42.2(9) . . . . ?
C15B C14B C20B O2B 135.6(6) . . . . ?
C13B C14B C20B N5B 137.4(6) . . . . ?
C15B C14B C20B N5B -44.8(8) . . . . ?
C1B C5B N1B C4B -0.3(8) . . . . ?
C3B C4B N1B C5B 2.4(8) . . . . ?
C10B C4B N1B C5B -176.2(5) . . . . ?
N3B C6B N2B C1B 176.2(5) . . . . ?
S1B C6B N2B C1B -2.2(8) . . . . ?
N3B C6B N2B C8B -2.7(6) . . . . ?
S1B C6B N2B C8B 178.9(4) . . . . ?
C5B C1B N2B C6B -129.1(6) . . . . ?
C2B C1B N2B C6B 51.3(8) . . . . ?
C5B C1B N2B C8B 49.8(8) . . . . ?
C2B C1B N2B C8B -129.9(6) . . . . ?
O1B C8B N2B C6B -174.4(6) . . . . ?
C7B C8B N2B C6B 5.6(6) . . . . ?
O1B C8B N2B C1B 6.6(9) . . . . ?
C7B C8B N2B C1B -173.4(5) . . . . ?
N2B C6B N3B C11B 176.2(5) . . . . ?
S1B C6B N3B C11B -5.4(8) . . . . ?
N2B C6B N3B C7B -1.5(6) . . . . ?
S1B C6B N3B C7B 176.8(4) . . . . ?
C16B C11B N3B C6B -86.9(7) . . . . ?
C12B C11B N3B C6B 95.6(7) . . . . ?
C16B C11B N3B C7B 90.6(7) . . . . ?
C12B C11B N3B C7B -86.9(7) . . . . ?
C8B C7B N3B C6B 4.7(6) . . . . ?
C18B C7B N3B C6B 132.0(6) . . . . ?
C17B C7B N3B C6B -119.8(6) . . . . ?
C8B C7B N3B C11B -173.0(5) . . . . ?
C18B C7B N3B C11B -45.7(8) . . . . ?
C17B C7B N3B C11B 62.4(7) . . . . ?
O2B C20B N5B C21B -4.1(11) . . . . ?
C14B C20B N5B C21B 176.4(6) . . . . ?
C5C C1C C2C C3C -2.9(8) . . . . ?
N2C C1C C2C C3C 179.7(5) . . . . ?
C1C C2C C3C C4C 0.6(8) . . . . ?
C1C C2C C3C C9C -178.2(5) . . . . ?
C2C C3C C4C N1C 2.2(9) . . . . ?
C9C C3C C4C N1C -179.1(6) . . . . ?
C2C C3C C4C C10C -176.9(5) . . . . ?
C9C C3C C4C C10C 1.9(9) . . . . ?
C2C C1C C5C N1C 2.9(9) . . . . ?
N2C C1C C5C N1C -179.6(5) . . . . ?
N3C C7C C8C O1C -178.7(7) . . . . ?
C18C C7C C8C O1C 50.7(9) . . . . ?
C17C C7C C8C O1C -48.1(9) . . . . ?
N3C C7C C8C N2C 1.6(6) . . . . ?
C18C C7C C8C N2C -129.0(5) . . . . ?
C17C C7C C8C N2C 132.2(5) . . . . ?
C2C C3C C9C F2C -0.8(8) . . . . ?
C4C C3C C9C F2C -179.6(5) . . . . ?
C2C C3C C9C F1C 120.5(6) . . . . ?
C4C C3C C9C F1C -58.2(8) . . . . ?
C2C C3C C9C F3C -121.3(6) . . . . ?
C4C C3C C9C F3C 59.9(8) . . . . ?
C16C C11C C12C C13C -0.3(9) . . . . ?
N3C C11C C12C C13C 179.5(5) . . . . ?
C11C C12C C13C F4C 174.0(6) . . . . ?
C11C C12C C13C C14C 0.7(9) . . . . ?
F4C C13C C14C C15C -173.2(6) . . . . ?
C12C C13C C14C C15C -0.3(9) . . . . ?
F4C C13C C14C C20C 3.2(9) . . . . ?
C12C C13C C14C C20C 176.1(6) . . . . ?
C13C C14C C15C F5C 177.5(6) . . . . ?
C13C C14C C15C C16C -0.6(9) . . . . ?
C20C C14C C15C C16C -177.1(5) . . . . ?
C14C C15C C16C C11C 1.0(9) . . . . ?
C12C C11C C16C C15C -0.6(9) . . . . ?
N3C C11C C16C C15C 179.6(5) . . . . ?
N3C C7C C17C C19C -142.9(5) . . . . ?
C8C C7C C17C C19C 96.3(5) . . . . ?
C18C C7C C17C C19C -18.4(4) . . . . ?
N3C C7C C18C C19C 143.0(5) . . . . ?
C8C C7C C18C C19C -96.0(5) . . . . ?
C17C C7C C18C C19C 18.3(4) . . . . ?
C7C C17C C19C C18C 18.4(4) . . . . ?
C7C C18C C19C C17C -18.6(5) . . . . ?
C13C C14C C20C O2C -131.7(6) . . . . ?
C15C C14C C20C O2C 44.5(8) . . . . ?
C13C C14C C20C N5C 45.5(8) . . . . ?
C15C C14C C20C N5C -138.2(6) . . . . ?
C1C C5C N1C C4C -0.2(9) . . . . ?
C3C C4C N1C C5C -2.3(9) . . . . ?
C10C C4C N1C C5C 176.8(5) . . . . ?
N3C C6C N2C C8C 3.9(6) . . . . ?
S1C C6C N2C C8C -177.4(5) . . . . ?
N3C C6C N2C C1C -176.8(5) . . . . ?
S1C C6C N2C C1C 1.8(8) . . . . ?
O1C C8C N2C C6C 176.8(6) . . . . ?
C7C C8C N2C C6C -3.4(6) . . . . ?
O1C C8C N2C C1C -2.5(10) . . . . ?
C7C C8C N2C C1C 177.3(5) . . . . ?
C5C C1C N2C C6C 126.2(6) . . . . ?
C2C C1C N2C C6C -56.3(8) . . . . ?
C5C C1C N2C C8C -54.6(8) . . . . ?
C2C C1C N2C C8C 122.9(6) . . . . ?
N2C C6C N3C C11C -178.3(5) . . . . ?
S1C C6C N3C C11C 3.1(8) . . . . ?
N2C C6C N3C C7C -2.8(6) . . . . ?
S1C C6C N3C C7C 178.5(4) . . . . ?
C12C C11C N3C C6C 78.3(7) . . . . ?
C16C C11C N3C C6C -101.9(7) . . . . ?
C12C C11C N3C C7C -96.7(7) . . . . ?
C16C C11C N3C C7C 83.1(7) . . . . ?
C8C C7C N3C C6C 0.8(6) . . . . ?
C18C C7C N3C C6C 127.1(6) . . . . ?
C17C C7C N3C C6C -125.1(5) . . . . ?
C8C C7C N3C C11C 176.2(5) . . . . ?
C18C C7C N3C C11C -57.5(8) . . . . ?
C17C C7C N3C C11C 50.4(7) . . . . ?
O2C C20C N5C C21C 2.0(10) . . . . ?
C14C C20C N5C C21C -175.1(6) . . . . ?
C5D C1D C2D C3D 0.0(8) . . . . ?
N2D C1D C2D C3D 179.5(5) . . . . ?
C1D C2D C3D C4D 2.0(8) . . . . ?
C1D C2D C3D C9D -175.9(5) . . . . ?
C2D C3D C4D N1D -3.1(9) . . . . ?
C9D C3D C4D N1D 174.8(5) . . . . ?
C2D C3D C4D C10D 178.0(5) . . . . ?
C9D C3D C4D C10D -4.1(9) . . . . ?
C2D C1D C5D N1D -1.1(9) . . . . ?
N2D C1D C5D N1D 179.4(5) . . . . ?
N3D C7D C8D O1D -176.6(6) . . . . ?
C18D C7D C8D O1D 53.5(9) . . . . ?
C17D C7D C8D O1D -45.6(9) . . . . ?
N3D C7D C8D N2D 6.9(6) . . . . ?
C18D C7D C8D N2D -123.0(5) . . . . ?
C17D C7D C8D N2D 137.9(5) . . . . ?
C2D C3D C9D F2D 2.0(8) . . . . ?
C4D C3D C9D F2D -175.8(5) . . . . ?
C2D C3D C9D F1D 122.9(6) . . . . ?
C4D C3D C9D F1D -55.0(7) . . . . ?
C2D C3D C9D F3D -117.8(6) . . . . ?
C4D C3D C9D F3D 64.4(7) . . . . ?
C16D C11D C12D C13D 3.5(9) . . . . ?
N3D C11D C12D C13D 179.1(5) . . . . ?
C11D C12D C13D F4D -179.7(6) . . . . ?
C11D C12D C13D C14D -2.8(9) . . . . ?
F4D C13D C14D C15D 177.9(6) . . . . ?
C12D C13D C14D C15D 0.8(9) . . . . ?
F4D C13D C14D C20D -5.7(9) . . . . ?
C12D C13D C14D C20D 177.2(6) . . . . ?
C13D C14D C15D F5D 178.2(8) . . . . ?
C20D C14D C15D F5D 1.9(11) . . . . ?
C13D C14D C15D C16D 0.6(9) . . . . ?
C20D C14D C15D C16D -175.7(6) . . . . ?
C12D C11D C16D C15D -2.2(9) . . . . ?
N3D C11D C16D C15D -177.6(5) . . . . ?
F5D C15D C16D C11D -177.4(8) . . . . ?
C14D C15D C16D C11D 0.1(9) . . . . ?
N3D C7D C17D C19D -140.4(6) . . . . ?
C8D C7D C17D C19D 97.6(5) . . . . ?
C18D C7D C17D C19D -16.6(5) . . . . ?
N3D C7D C18D C19D 140.3(5) . . . . ?
C8D C7D C18D C19D -99.2(5) . . . . ?
C17D C7D C18D C19D 16.5(5) . . . . ?
C7D C17D C19D C18D 16.5(5) . . . . ?
C7D C18D C19D C17D -16.6(5) . . . . ?
C13D C14D C20D O2D -43.0(9) . . . . ?
C15D C14D C20D O2D 133.2(7) . . . . ?
C13D C14D C20D N5D 136.5(7) . . . . ?
C15D C14D C20D N5D -47.3(9) . . . . ?
C1D C5D N1D C4D 0.1(8) . . . . ?
C3D C4D N1D C5D 2.0(8) . . . . ?
C10D C4D N1D C5D -179.0(5) . . . . ?
N3D C6D N2D C8D 5.0(7) . . . . ?
S1D C6D N2D C8D -173.7(5) . . . . ?
N3D C6D N2D C1D 174.4(5) . . . . ?
S1D C6D N2D C1D -4.3(9) . . . . ?
O1D C8D N2D C6D 175.6(6) . . . . ?
C7D C8D N2D C6D -7.7(7) . . . . ?
O1D C8D N2D C1D 6.2(10) . . . . ?
C7D C8D N2D C1D -177.1(5) . . . . ?
C2D C1D N2D C6D -107.5(7) . . . . ?
C5D C1D N2D C6D 72.0(7) . . . . ?
C2D C1D N2D C8D 60.7(8) . . . . ?
C5D C1D N2D C8D -119.8(6) . . . . ?
N2D C6D N3D C11D -167.6(5) . . . . ?
S1D C6D N3D C11D 11.0(9) . . . . ?
N2D C6D N3D C7D 0.0(7) . . . . ?
S1D C6D N3D C7D 178.6(5) . . . . ?
C16D C11D N3D C6D -105.3(7) . . . . ?
C12D C11D N3D C6D 79.1(8) . . . . ?
C16D C11D N3D C7D 88.3(8) . . . . ?
C12D C11D N3D C7D -87.3(7) . . . . ?
C8D C7D N3D C6D -4.4(7) . . . . ?
C18D C7D N3D C6D 121.0(6) . . . . ?
C17D C7D N3D C6D -132.0(6) . . . . ?
C8D C7D N3D C11D 163.3(5) . . . . ?
C18D C7D N3D C11D -71.4(8) . . . . ?
C17D C7D N3D C11D 35.7(8) . . . . ?
O2D C20D N5D C21D -2.4(10) . . . . ?
C14D C20D N5D C21D 178.1(6) . . . . ?
O3A C22A N6A C23A -4.3(12) . . . . ?
O3A C22A N6A C24A -175.4(7) . . . . ?
O3B C22B N6B C24B 178.6(6) . . . . ?
O3B C22B N6B C23B 3.8(10) . . . . ?

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
_geom_hbond_publ_flag
N5A H5NA O2B 0.80(6) 2.10(6) 2.870(6) 162(6) . yes
N5B H5NB O2D 0.94(6) 1.85(6) 2.761(7) 163(5) . yes
N5C H5NC O2A 0.82(6) 2.00(6) 2.811(7) 172(6) . yes
N5D H5ND O2C 0.92(6) 2.03(6) 2.939(7) 170(5) 1_565 yes
C2A H2A O3A 0.95 2.43 3.226(8) 141 . yes
C16B H16B S1D 0.95 2.83 3.680(6) 149 . yes
C17B H17D F3A 0.99 2.55 3.348(7) 137 2_665 yes
C18B H18D O3B 0.99 2.45 3.405(7) 162 . yes
C21C H21I S1B 0.98 2.84 3.746(7) 154 2_556 yes
C2D H2D O3B 0.95 2.55 3.334(8) 140 . yes
C24A H24B N4A 0.98 2.61 3.592(11) 180 1_455 yes

_refine_diff_density_max         0.678
_refine_diff_density_min         -0.756
_refine_diff_density_rms         0.108

####################################################################### 
# 
# 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_a_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2151552'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2022-02-11 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 F4 N5 O2 S'
_chemical_formula_sum            'C21 H15 F4 N5 O2 S'
_chemical_formula_weight         477.44

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                   17.7813(6)
_cell_length_b                   13.0140(4)
_cell_length_c                   18.4676(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.8839(11)
_cell_angle_gamma                90
_cell_volume                     4196.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9982
_cell_measurement_theta_min      2.246
_cell_measurement_theta_max      30.501

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_F_000             1952
_exptl_transmission_factor_min   0.7323
_exptl_transmission_factor_max   0.8622
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.220
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42501
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.139
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9154
_reflns_number_gt                7500
_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       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0461P)²+3.5415P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9154
_refine_ls_number_parameters     616
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.27638(3) 0.41307(4) 0.37722(3) 0.02259(11) Uani 1 1 d . . . . .
F1 F 0.33750(7) 0.80846(10) 0.46622(7) 0.0322(3) Uani 1 1 d . . . . .
F11 F -0.00964(10) 0.32512(14) 0.34368(11) 0.0748(6) Uani 1 1 d . . . . .
F12 F -0.07980(7) 0.26902(13) 0.24320(8) 0.0499(4) Uani 1 1 d . . . . .
F13 F -0.01925(7) 0.16607(11) 0.32234(7) 0.0407(3) Uani 1 1 d . . . . .
O11 O 0.49629(9) 0.80746(11) 0.54435(7) 0.0280(3) Uani 1 1 d . . . . .
O12 O 0.18793(9) 0.47655(12) 0.10802(8) 0.0338(4) Uani 1 1 d . . . . .
N11 N 0.53869(9) 0.87800(12) 0.44733(9) 0.0197(3) Uani 1 1 d . . . . .
H11 H 0.5341(13) 0.8764(17) 0.4003(13) 0.023(6) Uiso 1 1 d . . . . .
N12 N 0.29576(9) 0.55514(12) 0.27622(8) 0.0193(3) Uani 1 1 d . . . . .
N13 N 0.21519(9) 0.43184(12) 0.23165(8) 0.0186(3) Uani 1 1 d . . . . .
N14 N 0.12266(10) 0.18963(13) 0.16441(9) 0.0243(4) Uani 1 1 d . . . . .
N15 N -0.03902(12) 0.04786(15) 0.16847(11) 0.0377(5) Uani 1 1 d . . . . .
C11 C 0.26266(10) 0.46884(14) 0.29558(10) 0.0181(4) Uani 1 1 d . . . . .
C12 C 0.27211(11) 0.58193(14) 0.19844(10) 0.0192(4) Uani 1 1 d . . . . .
C13 C 0.22045(11) 0.49322(15) 0.17002(10) 0.0218(4) Uani 1 1 d . . . . .
C14 C 0.33213(12) 0.60690(16) 0.15020(11) 0.0255(4) Uani 1 1 d . . . . .
H14A H 0.380917 0.634439 0.178289 0.031 Uiso 1 1 calc R U . . .
H14B H 0.341406 0.549851 0.117530 0.031 Uiso 1 1 calc R U . . .
C15 C 0.27711(12) 0.69027(16) 0.11112(11) 0.0259(4) Uani 1 1 d . . . . .
H15A H 0.245568 0.667387 0.063854 0.031 Uiso 1 1 calc R U . . .
H15B H 0.302386 0.756710 0.105224 0.031 Uiso 1 1 calc R U . . .
C16 C 0.23437(12) 0.68790(15) 0.17666(11) 0.0241(4) Uani 1 1 d . . . . .
H16A H 0.177920 0.685183 0.161795 0.029 Uiso 1 1 calc R U . . .
H16B H 0.250353 0.742586 0.213630 0.029 Uiso 1 1 calc R U . . .
C21 C 0.34686(11) 0.61763(14) 0.32729(10) 0.0190(4) Uani 1 1 d . . . . .
C22 C 0.31660(11) 0.68383(15) 0.37319(10) 0.0210(4) Uani 1 1 d . . . . .
H22A H 0.262944 0.687309 0.371607 0.025 Uiso 1 1 calc R U . . .
C23 C 0.36650(11) 0.74436(14) 0.42113(10) 0.0209(4) Uani 1 1 d . . . . .
C24 C 0.44501(11) 0.74365(14) 0.42407(10) 0.0184(4) Uani 1 1 d . . . . .
C25 C 0.47368(11) 0.67718(15) 0.37673(11) 0.0223(4) Uani 1 1 d . . . . .
H25A H 0.527167 0.675483 0.377142 0.027 Uiso 1 1 calc R U . . .
C26 C 0.42501(11) 0.61338(14) 0.32895(11) 0.0217(4) Uani 1 1 d . . . . .
H26A H 0.445162 0.567178 0.297646 0.026 Uiso 1 1 calc R U . . .
C27 C 0.49636(11) 0.81237(14) 0.47784(10) 0.0189(4) Uani 1 1 d . . . . .
C28 C 0.59167(12) 0.94886(15) 0.49170(11) 0.0253(4) Uani 1 1 d . . . . .
H28A H 0.622410 0.983641 0.460266 0.038 Uiso 0.06(2) 1 calc R U P . .
H28B H 0.625521 0.910668 0.530518 0.038 Uiso 0.06(2) 1 calc R U P . .
H28C H 0.562754 1.000001 0.514188 0.038 Uiso 0.06(2) 1 calc R U P . .
H28D H 0.584714 0.945899 0.543049 0.038 Uiso 0.94(2) 1 calc R U P . .
H28E H 0.581602 1.018872 0.472796 0.038 Uiso 0.94(2) 1 calc R U P . .
H28F H 0.644369 0.929539 0.489127 0.038 Uiso 0.94(2) 1 calc R U P . .
C31 C 0.17213(11) 0.26794(15) 0.17849(11) 0.0225(4) Uani 1 1 d . . . . .
H31A H 0.214355 0.269812 0.153754 0.027 Uiso 1 1 calc R U . . .
C32 C 0.16471(10) 0.34627(14) 0.22735(10) 0.0190(4) Uani 1 1 d . . . . .
C33 C 0.10563(11) 0.34369(15) 0.26653(11) 0.0214(4) Uani 1 1 d . . . . .
H33A H 0.100577 0.395423 0.301584 0.026 Uiso 1 1 calc R U . . .
C34 C 0.05408(10) 0.26291(15) 0.25278(10) 0.0202(4) Uani 1 1 d . . . . .
C35 C 0.06428(11) 0.18939(14) 0.20077(10) 0.0201(4) Uani 1 1 d . . . . .
C36 C 0.00829(12) 0.10818(16) 0.18161(11) 0.0261(4) Uani 1 1 d . . . . .
C37 C -0.01420(12) 0.25717(17) 0.29017(12) 0.0287(5) Uani 1 1 d . . . . .
S2 S 0.31926(3) 0.26992(3) 0.56165(3) 0.01943(11) Uani 1 1 d . . . . .
F2A F 0.38813(9) 0.58938(12) 0.78798(8) 0.0299(5) Uani 0.795(4) 1 d . . P A 1
F2B F 0.4966(3) 0.5883(4) 0.5682(3) 0.0245(16) Uani 0.205(4) 1 d . . P A 2
F21 F 0.25708(9) 0.06766(12) 0.34018(9) 0.0557(5) Uani 1 1 d . . . . .
F22 F 0.14989(8) -0.00235(11) 0.29420(7) 0.0397(3) Uani 1 1 d . . . . .
F23 F 0.22271(9) -0.07130(11) 0.38584(8) 0.0489(4) Uani 1 1 d . . . . .
O21 O 0.54472(8) 0.62077(11) 0.78601(7) 0.0262(3) Uani 1 1 d . . . . .
O22 O 0.05935(8) 0.41877(11) 0.47390(9) 0.0302(3) Uani 1 1 d . . . . .
N21 N 0.54127(10) 0.73258(13) 0.69139(9) 0.0235(4) Uani 1 1 d . . . . .
H21 H 0.5197(13) 0.7489(17) 0.6485(13) 0.022(6) Uiso 1 1 d . . . . .
N22 N 0.24803(8) 0.45194(11) 0.56364(8) 0.0168(3) Uani 1 1 d . . . . .
N23 N 0.17380(8) 0.33037(11) 0.50542(8) 0.0168(3) Uani 1 1 d . . . . .
N24 N 0.05542(9) 0.09698(12) 0.47545(9) 0.0212(3) Uani 1 1 d . . . . .
N25 N 0.04193(12) -0.13979(14) 0.39659(11) 0.0357(4) Uani 1 1 d . . . . .
C41 C 0.24756(10) 0.35235(14) 0.54339(9) 0.0160(3) Uani 1 1 d . . . . .
C42 C 0.17553(10) 0.50467(14) 0.53630(10) 0.0183(4) Uani 1 1 d . . . . .
C43 C 0.12633(11) 0.41721(14) 0.50125(11) 0.0202(4) Uani 1 1 d . . . . .
C44 C 0.13611(11) 0.57229(15) 0.58744(11) 0.0233(4) Uani 1 1 d . . . . .
H44A H 0.091802 0.538889 0.603143 0.028 Uiso 1 1 calc R U . . .
H44B H 0.171883 0.601198 0.630210 0.028 Uiso 1 1 calc R U . . .
C45 C 0.11377(11) 0.64845(15) 0.52287(12) 0.0246(4) Uani 1 1 d . . . . .
H45A H 0.124126 0.721221 0.536932 0.029 Uiso 1 1 calc R U . . .
H45B H 0.060755 0.639555 0.495288 0.029 Uiso 1 1 calc R U . . .
C46 C 0.17524(11) 0.59920(14) 0.48474(11) 0.0206(4) Uani 1 1 d . . . . .
H46A H 0.224320 0.637256 0.492537 0.025 Uiso 1 1 calc R U . . .
H46B H 0.157020 0.583717 0.431847 0.025 Uiso 1 1 calc R U . . .
C51 C 0.31482(10) 0.50263(13) 0.60297(10) 0.0169(4) Uani 1 1 d . . . . .
C52 C 0.32027(11) 0.52222(14) 0.67763(10) 0.0200(4) Uani 1 1 d . . . . .
H52A H 0.280521 0.501948 0.702487 0.024 Uiso 1 1 calc R U . . .
C53 C 0.38475(11) 0.57186(14) 0.71510(10) 0.0196(4) Uani 1 1 d . . . . .
H53A H 0.388566 0.585232 0.766233 0.024 Uiso 0.205(4) 1 calc R U P A 2
C54 C 0.44414(10) 0.60293(14) 0.68099(10) 0.0184(4) Uani 1 1 d . . . . .
C55 C 0.43641(11) 0.58221(14) 0.60552(10) 0.0200(4) Uani 1 1 d . . . . .
H55A H 0.476072 0.602621 0.580585 0.024 Uiso 0.795(4) 1 calc R U P A 1
C56 C 0.37254(11) 0.53279(14) 0.56622(10) 0.0194(4) Uani 1 1 d . . . . .
H56A H 0.368268 0.519734 0.514991 0.023 Uiso 1 1 calc R U . . .
C57 C 0.51479(11) 0.65289(14) 0.72453(10) 0.0199(4) Uani 1 1 d . . . . .
C58 C 0.61141(12) 0.78605(17) 0.72392(12) 0.0295(5) Uani 1 1 d . . . . .
H58A H 0.610051 0.856143 0.704320 0.044 Uiso 1 1 calc R U . . .
H58B H 0.655528 0.749387 0.711735 0.044 Uiso 1 1 calc R U . . .
H58C H 0.615874 0.788623 0.777594 0.044 Uiso 1 1 calc R U . . .
C61 C 0.08235(10) 0.18988(14) 0.49751(10) 0.0195(4) Uani 1 1 d . . . . .
H61A H 0.055427 0.229365 0.527603 0.023 Uiso 1 1 calc R U . . .
C62 C 0.14801(10) 0.23151(14) 0.47847(10) 0.0171(4) Uani 1 1 d . . . . .
C63 C 0.18632(10) 0.17699(14) 0.43218(10) 0.0190(4) Uani 1 1 d . . . . .
H63A H 0.230071 0.204985 0.416774 0.023 Uiso 1 1 calc R U . . .
C64 C 0.15893(10) 0.08020(14) 0.40894(10) 0.0196(4) Uani 1 1 d . . . . .
C65 C 0.09419(11) 0.04316(14) 0.43327(10) 0.0200(4) Uani 1 1 d . . . . .
C66 C 0.06412(12) -0.05923(16) 0.41291(11) 0.0251(4) Uani 1 1 d . . . . .
C67 C 0.19740(12) 0.01853(16) 0.35755(11) 0.0267(4) Uani 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 C11 1.6494(19) . ?
F1 C23 1.348(2) . ?
F11 C37 1.317(3) . ?
F12 C37 1.325(3) . ?
F13 C37 1.337(3) . ?
O11 C27 1.230(2) . ?
O12 C13 1.201(2) . ?
N11 C27 1.332(2) . ?
N11 C28 1.455(2) . ?
N11 H11 0.86(2) . ?
N12 C11 1.347(2) . ?
N12 C21 1.433(2) . ?
N12 C12 1.461(2) . ?
N13 C11 1.401(2) . ?
N13 C13 1.408(2) . ?
N13 C32 1.423(2) . ?
N14 C35 1.339(3) . ?
N14 C31 1.339(2) . ?
N15 C36 1.143(3) . ?
C12 C13 1.507(3) . ?
C12 C14 1.548(3) . ?
C12 C16 1.553(3) . ?
C14 C15 1.545(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.546(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C21 C26 1.385(3) . ?
C21 C22 1.387(3) . ?
C22 C23 1.377(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.387(3) . ?
C24 C25 1.393(3) . ?
C24 C27 1.509(3) . ?
C25 C26 1.389(3) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C28 H28D 0.9800 . ?
C28 H28E 0.9800 . ?
C28 H28F 0.9800 . ?
C31 C32 1.384(3) . ?
C31 H31A 0.9500 . ?
C32 C33 1.384(3) . ?
C33 C34 1.386(3) . ?
C33 H33A 0.9500 . ?
C34 C35 1.392(3) . ?
C34 C37 1.508(3) . ?
C35 C36 1.449(3) . ?
S2 C41 1.6516(18) . ?
F2A C53 1.355(2) . ?
F2B C55 1.381(5) . ?
F21 C67 1.329(2) . ?
F22 C67 1.335(2) . ?
F23 C67 1.324(3) . ?
O21 C57 1.232(2) . ?
O22 C43 1.203(2) . ?
N21 C57 1.334(2) . ?
N21 C58 1.455(3) . ?
N21 H21 0.84(2) . ?
N22 C41 1.349(2) . ?
N22 C51 1.431(2) . ?
N22 C42 1.464(2) . ?
N23 C41 1.395(2) . ?
N23 C43 1.404(2) . ?
N23 C62 1.424(2) . ?
N24 C65 1.332(2) . ?
N24 C61 1.335(2) . ?
N25 C66 1.141(3) . ?
C42 C43 1.505(3) . ?
C42 C44 1.552(3) . ?
C42 C46 1.555(3) . ?
C44 C45 1.544(3) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.547(3) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C51 C52 1.387(3) . ?
C51 C56 1.390(3) . ?
C52 C53 1.382(3) . ?
C52 H52A 0.9500 . ?
C53 C54 1.388(3) . ?
C53 H53A 0.9500 . ?
C54 C55 1.401(3) . ?
C54 C57 1.505(3) . ?
C55 C56 1.385(3) . ?
C55 H55A 0.9500 . ?
C56 H56A 0.9500 . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C61 C62 1.391(3) . ?
C61 H61A 0.9500 . ?
C62 C63 1.385(3) . ?
C63 C64 1.389(3) . ?
C63 H63A 0.9500 . ?
C64 C65 1.398(3) . ?
C64 C67 1.503(3) . ?
C65 C66 1.458(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
C27 N11 C28 121.72(17) . . ?
C27 N11 H11 117.4(15) . . ?
C28 N11 H11 120.9(15) . . ?
C11 N12 C21 123.57(15) . . ?
C11 N12 C12 113.63(15) . . ?
C21 N12 C12 122.74(15) . . ?
C11 N13 C13 111.40(15) . . ?
C11 N13 C32 126.11(15) . . ?
C13 N13 C32 122.44(15) . . ?
C35 N14 C31 116.59(16) . . ?
N12 C11 N13 106.67(15) . . ?
N12 C11 S1 127.79(14) . . ?
N13 C11 S1 125.51(14) . . ?
N12 C12 C13 101.72(14) . . ?
N12 C12 C14 120.95(16) . . ?
C13 C12 C14 113.68(16) . . ?
N12 C12 C16 119.78(15) . . ?
C13 C12 C16 112.64(16) . . ?
C14 C12 C16 88.61(14) . . ?
O12 C13 N13 125.07(18) . . ?
O12 C13 C12 128.51(18) . . ?
N13 C13 C12 106.40(15) . . ?
C15 C14 C12 88.38(14) . . ?
C15 C14 H14A 113.9 . . ?
C12 C14 H14A 113.9 . . ?
C15 C14 H14B 113.9 . . ?
C12 C14 H14B 113.9 . . ?
H14A C14 H14B 111.1 . . ?
C14 C15 C16 88.96(14) . . ?
C14 C15 H15A 113.8 . . ?
C16 C15 H15A 113.8 . . ?
C14 C15 H15B 113.8 . . ?
C16 C15 H15B 113.8 . . ?
H15A C15 H15B 111.0 . . ?
C15 C16 C12 88.18(14) . . ?
C15 C16 H16A 114.0 . . ?
C12 C16 H16A 114.0 . . ?
C15 C16 H16B 114.0 . . ?
C12 C16 H16B 114.0 . . ?
H16A C16 H16B 111.2 . . ?
C26 C21 C22 120.98(17) . . ?
C26 C21 N12 120.06(17) . . ?
C22 C21 N12 118.94(17) . . ?
C23 C22 C21 118.12(17) . . ?
C23 C22 H22A 120.9 . . ?
C21 C22 H22A 120.9 . . ?
F1 C23 C22 118.42(17) . . ?
F1 C23 C24 118.67(16) . . ?
C22 C23 C24 122.90(17) . . ?
C23 C24 C25 117.68(17) . . ?
C23 C24 C27 120.08(16) . . ?
C25 C24 C27 122.23(17) . . ?
C26 C25 C24 120.80(18) . . ?
C26 C25 H25A 119.6 . . ?
C24 C25 H25A 119.6 . . ?
C21 C26 C25 119.50(17) . . ?
C21 C26 H26A 120.3 . . ?
C25 C26 H26A 120.3 . . ?
O11 C27 N11 124.26(17) . . ?
O11 C27 C24 120.78(17) . . ?
N11 C27 C24 114.94(16) . . ?
N11 C28 H28A 109.5 . . ?
N11 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N11 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N11 C28 H28D 109.5 . . ?
H28A C28 H28D 141.1 . . ?
H28B C28 H28D 56.3 . . ?
H28C C28 H28D 56.3 . . ?
N11 C28 H28E 109.5 . . ?
H28A C28 H28E 56.3 . . ?
H28B C28 H28E 141.1 . . ?
H28C C28 H28E 56.3 . . ?
H28D C28 H28E 109.5 . . ?
N11 C28 H28F 109.5 . . ?
H28A C28 H28F 56.3 . . ?
H28B C28 H28F 56.3 . . ?
H28C C28 H28F 141.1 . . ?
H28D C28 H28F 109.5 . . ?
H28E C28 H28F 109.5 . . ?
N14 C31 C32 123.17(18) . . ?
N14 C31 H31A 118.4 . . ?
C32 C31 H31A 118.4 . . ?
C33 C32 C31 119.88(17) . . ?
C33 C32 N13 121.52(17) . . ?
C31 C32 N13 118.42(17) . . ?
C32 C33 C34 117.62(17) . . ?
C32 C33 H33A 121.2 . . ?
C34 C33 H33A 121.2 . . ?
C33 C34 C35 118.67(17) . . ?
C33 C34 C37 121.03(17) . . ?
C35 C34 C37 120.22(17) . . ?
N14 C35 C34 123.99(17) . . ?
N14 C35 C36 116.19(17) . . ?
C34 C35 C36 119.79(17) . . ?
N15 C36 C35 175.6(2) . . ?
F11 C37 F12 109.57(19) . . ?
F11 C37 F13 105.19(19) . . ?
F12 C37 F13 105.63(17) . . ?
F11 C37 C34 111.69(17) . . ?
F12 C37 C34 112.33(17) . . ?
F13 C37 C34 112.02(17) . . ?
C57 N21 C58 122.11(17) . . ?
C57 N21 H21 119.4(15) . . ?
C58 N21 H21 118.2(15) . . ?
C41 N22 C51 123.02(15) . . ?
C41 N22 C42 113.32(15) . . ?
C51 N22 C42 123.48(14) . . ?
C41 N23 C43 111.15(15) . . ?
C41 N23 C62 124.83(15) . . ?
C43 N23 C62 123.89(15) . . ?
C65 N24 C61 117.32(16) . . ?
N22 C41 N23 107.01(15) . . ?
N22 C41 S2 127.11(14) . . ?
N23 C41 S2 125.85(14) . . ?
N22 C42 C43 101.32(14) . . ?
N22 C42 C44 121.71(15) . . ?
C43 C42 C44 113.45(15) . . ?
N22 C42 C46 118.88(15) . . ?
C43 C42 C46 113.60(15) . . ?
C44 C42 C46 88.53(14) . . ?
O22 C43 N23 125.02(18) . . ?
O22 C43 C42 128.08(17) . . ?
N23 C43 C42 106.89(15) . . ?
C45 C44 C42 88.50(14) . . ?
C45 C44 H44A 113.9 . . ?
C42 C44 H44A 113.9 . . ?
C45 C44 H44B 113.9 . . ?
C42 C44 H44B 113.9 . . ?
H44A C44 H44B 111.1 . . ?
C44 C45 C46 89.12(14) . . ?
C44 C45 H45A 113.8 . . ?
C46 C45 H45A 113.8 . . ?
C44 C45 H45B 113.8 . . ?
C46 C45 H45B 113.8 . . ?
H45A C45 H45B 111.0 . . ?
C45 C46 C42 88.28(14) . . ?
C45 C46 H46A 113.9 . . ?
C42 C46 H46A 113.9 . . ?
C45 C46 H46B 113.9 . . ?
C42 C46 H46B 113.9 . . ?
H46A C46 H46B 111.1 . . ?
C52 C51 C56 120.93(17) . . ?
C52 C51 N22 118.99(16) . . ?
C56 C51 N22 120.07(16) . . ?
C53 C52 C51 118.62(17) . . ?
C53 C52 H52A 120.7 . . ?
C51 C52 H52A 120.7 . . ?
F2A C53 C52 116.92(17) . . ?
F2A C53 C54 120.45(17) . . ?
C52 C53 C54 122.62(17) . . ?
C52 C53 H53A 118.7 . . ?
C54 C53 H53A 118.7 . . ?
C53 C54 C55 117.09(17) . . ?
C53 C54 C57 120.87(16) . . ?
C55 C54 C57 122.00(17) . . ?
F2B C55 C56 113.7(3) . . ?
F2B C55 C54 123.1(3) . . ?
C56 C55 C54 121.83(17) . . ?
C56 C55 H55A 119.1 . . ?
C54 C55 H55A 119.1 . . ?
C55 C56 C51 118.90(17) . . ?
C55 C56 H56A 120.6 . . ?
C51 C56 H56A 120.6 . . ?
O21 C57 N21 123.89(18) . . ?
O21 C57 C54 121.16(17) . . ?
N21 C57 C54 114.95(16) . . ?
N21 C58 H58A 109.5 . . ?
N21 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
N21 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
N24 C61 C62 123.03(17) . . ?
N24 C61 H61A 118.5 . . ?
C62 C61 H61A 118.5 . . ?
C63 C62 C61 119.38(17) . . ?
C63 C62 N23 121.01(16) . . ?
C61 C62 N23 119.59(16) . . ?
C62 C63 C64 118.08(17) . . ?
C62 C63 H63A 121.0 . . ?
C64 C63 H63A 121.0 . . ?
C63 C64 C65 118.38(17) . . ?
C63 C64 C67 120.30(17) . . ?
C65 C64 C67 121.30(17) . . ?
N24 C65 C64 123.70(17) . . ?
N24 C65 C66 115.22(17) . . ?
C64 C65 C66 121.08(17) . . ?
N25 C66 C65 178.6(2) . . ?
F23 C67 F21 107.01(18) . . ?
F23 C67 F22 106.12(17) . . ?
F21 C67 F22 106.76(17) . . ?
F23 C67 C64 112.56(17) . . ?
F21 C67 C64 112.03(17) . . ?
F22 C67 C64 111.95(17) . . ?

_refine_diff_density_max         1.007
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.056

