# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_20180907y03_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1867988'
_audit_update_record             
;
2018-09-15 deposited with the CCDC.
2018-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'3-(2-Fluorophenyl)-3-((6-methoxybenzo[d]thiazol-2-yl)amino)-1-phenyl propan-1-one'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C23H19FN2O2S
_chemical_formula_sum            'C46 H37 F2 N4 O4 S2'
_chemical_formula_weight         811.91

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.434(7)
_cell_length_b                   10.662(10)
_cell_length_c                   44.27(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3981(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.20

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             1692
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29211
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         2.120
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_full        25.007
_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             6998
_reflns_number_gt                6258
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.750
_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0582P)²+4.5197P] 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 
;
 Flack x determined using 2394 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         6998
_refine_ls_number_parameters     582
_refine_ls_number_restraints     366
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1260
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.064
_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 0.1488(5) 0.1417(6) 0.46718(13) 0.044(2) Uani 0.651(8) 1 d G U P A 1
H1A H 0.259885 0.156336 0.467272 0.053 Uiso 0.651(8) 1 calc R U P A 1
C2 C 0.0699(7) 0.1165(7) 0.49407(10) 0.057(3) Uani 0.651(8) 1 d G U P A 1
H2A H 0.127091 0.113903 0.512545 0.069 Uiso 0.651(8) 1 calc R U P A 1
C3 C -0.0927(7) 0.0951(7) 0.49393(11) 0.067(3) Uani 0.651(8) 1 d G U P A 1
H3A H -0.146579 0.077901 0.512306 0.080 Uiso 0.651(8) 1 calc R U P A 1
C4 C -0.1764(5) 0.0989(7) 0.46689(14) 0.072(3) Uani 0.651(8) 1 d G U P A 1
H4A H -0.287457 0.084331 0.466794 0.086 Uiso 0.651(8) 1 calc R U P A 1
C5 C -0.0975(7) 0.1242(6) 0.44000(11) 0.051(2) Uani 0.651(8) 1 d G U P A 1
H5A H -0.154667 0.126763 0.421521 0.061 Uiso 0.651(8) 1 calc R U P A 1
C6 C 0.0651(6) 0.1455(6) 0.44014(10) 0.0325(19) Uani 0.651(8) 1 d G U P A 1
C7 C 0.1541(6) 0.1669(5) 0.41301(12) 0.040 Uani 1 1 d . U . . .
C8 C 0.3032(6) 0.2452(5) 0.41240(11) 0.034 Uani 1 1 d . U . . .
H8A H 0.389934 0.196935 0.422013 0.041 Uiso 1 1 calc R U . . .
H8B H 0.285647 0.321586 0.424652 0.041 Uiso 1 1 calc R U . . .
C9 C 0.3560(5) 0.2843(4) 0.38077(9) 0.0245(9) Uani 1 1 d . U . . .
H9A H 0.344154 0.210442 0.367047 0.029 Uiso 1 1 calc R U . . .
C10 C 0.5292(5) 0.3237(4) 0.38068(9) 0.0240(9) Uani 1 1 d . U . . .
C11 C 0.6405(5) 0.2636(5) 0.36266(10) 0.0277(10) Uani 1 1 d . U . . .
H11A H 0.607908 0.196853 0.349859 0.033 Uiso 1 1 calc R U . . .
C12 C 0.7981(6) 0.2992(5) 0.36306(11) 0.0372(12) Uani 1 1 d . U . . .
H12A H 0.872909 0.257017 0.350650 0.045 Uiso 1 1 calc R U . . .
C13 C 0.8471(7) 0.3970(5) 0.38167(12) 0.0403(12) Uani 1 1 d . U . . .
H13A H 0.955550 0.420909 0.382036 0.048 Uiso 1 1 calc R U . . .
C14 C 0.7392(6) 0.4593(5) 0.39953(10) 0.0359(11) Uani 1 1 d . U . . .
H14A H 0.771526 0.526446 0.412221 0.043 Uiso 1 1 calc R U . . .
C15 C 0.5836(5) 0.4216(5) 0.39851(10) 0.0275(10) Uani 1 1 d . U . . .
C16 C 0.2225(5) 0.4051(4) 0.34027(9) 0.0229(9) Uani 1 1 d . U . . .
C17 C 0.1290(5) 0.4982(5) 0.29875(9) 0.0262(10) Uani 1 1 d . U . . .
C18 C 0.0575(6) 0.5879(5) 0.28058(10) 0.0305(10) Uani 1 1 d . U . . .
H18A H 0.016549 0.662664 0.289250 0.037 Uiso 1 1 calc R U . . .
C19 C 0.0461(6) 0.5677(5) 0.24954(11) 0.0339(11) Uani 1 1 d . U . . .
H19A H -0.002798 0.629096 0.237106 0.041 Uiso 1 1 calc R U . . .
C20 C 0.1056(6) 0.4585(5) 0.23660(10) 0.0307(11) Uani 1 1 d . U . . .
C21 C 0.1776(5) 0.3662(5) 0.25432(10) 0.0302(11) Uani 1 1 d . U . . .
H21A H 0.219555 0.292006 0.245539 0.036 Uiso 1 1 calc R U . . .
C22 C 0.1857(5) 0.3871(4) 0.28526(10) 0.0271(10) Uani 1 1 d . U . . .
C23 C 0.0879(8) 0.5344(6) 0.18606(13) 0.0550(15) Uani 1 1 d . U . . .
H23A H 0.080737 0.503528 0.165255 0.082 Uiso 1 1 calc R U . . .
H23B H -0.005602 0.585386 0.190704 0.082 Uiso 1 1 calc R U . . .
H23C H 0.183719 0.585556 0.188312 0.082 Uiso 1 1 calc R U . . .
C24 C 0.2969(6) 0.8653(5) 0.25622(10) 0.0345(11) Uani 1 1 d . U . . .
H24A H 0.243545 0.797163 0.265567 0.041 Uiso 1 1 calc R U . . .
C25 C 0.2991(6) 0.8747(5) 0.22490(11) 0.0393(12) Uani 1 1 d . U . . .
H25A H 0.247546 0.812784 0.212992 0.047 Uiso 1 1 calc R U . . .
C26 C 0.3751(6) 0.9729(5) 0.21113(12) 0.0407(12) Uani 1 1 d . U . . .
H26A H 0.377734 0.978385 0.189720 0.049 Uiso 1 1 calc R U . . .
C27 C 0.4481(7) 1.0639(6) 0.22851(12) 0.0454(14) Uani 1 1 d . U . . .
H27A H 0.498560 1.132823 0.218893 0.055 Uiso 1 1 calc R U . . .
C28 C 0.4487(6) 1.0559(5) 0.25977(11) 0.0368(12) Uani 1 1 d . U . . .
H28A H 0.500419 1.118420 0.271455 0.044 Uiso 1 1 calc R U . . .
C29 C 0.3727(5) 0.9553(4) 0.27406(10) 0.0265(10) Uani 1 1 d . U . . .
C30 C 0.3733(5) 0.9488(4) 0.30764(10) 0.0263(10) Uani 1 1 d . U . . .
C31 C 0.2875(6) 0.8414(5) 0.32306(9) 0.0304(10) Uani 1 1 d . U . . .
H31A H 0.320825 0.761612 0.313567 0.036 Uiso 1 1 calc R U . . .
H31B H 0.172121 0.851062 0.319642 0.036 Uiso 1 1 calc R U . . .
C32 C 0.3182(5) 0.8333(4) 0.35725(9) 0.0250(10) Uani 1 1 d . U . . .
C33 C 0.4935(5) 0.8105(7) 0.36214(16) 0.019(2) Uani 0.552(14) 1 d G U P B 1
C34 C 0.5667(7) 0.7075(6) 0.34886(16) 0.036(3) Uani 0.552(14) 1 d G U P B 1
H34A H 0.505687 0.648879 0.337634 0.043 Uiso 0.552(14) 1 calc R U P B 1
C35 C 0.7292(7) 0.6903(7) 0.35200(17) 0.048(3) Uani 0.552(14) 1 d G U P B 1
H35A H 0.779289 0.619927 0.342924 0.057 Uiso 0.552(14) 1 calc R U P B 1
C36 C 0.8186(5) 0.7761(8) 0.36842(17) 0.040(3) Uani 0.552(14) 1 d G U P B 1
H36A H 0.929633 0.764309 0.370572 0.048 Uiso 0.552(14) 1 calc R U P B 1
C37 C 0.7453(7) 0.8790(7) 0.38171(15) 0.046(3) Uani 0.552(14) 1 d G U P B 1
H37A H 0.806378 0.937643 0.392931 0.055 Uiso 0.552(14) 1 calc R U P B 1
C38 C 0.5828(7) 0.8962(6) 0.37856(15) 0.030(2) Uani 0.552(14) 1 d G U P B 1
F2 F 0.5007(6) 1.0049(4) 0.39200(9) 0.0575(11) Uani 0.8 1 d . U P B 1
C39 C 0.1973(5) 0.7037(4) 0.39774(9) 0.0237(9) Uani 1 1 d . U . . .
C40 C 0.1117(5) 0.6083(4) 0.43887(9) 0.0250(10) Uani 1 1 d . U . . .
C41 C 0.0425(5) 0.5159(5) 0.45720(10) 0.0289(10) Uani 1 1 d . U . . .
H41A H 0.006496 0.439314 0.448650 0.035 Uiso 1 1 calc R U . . .
C42 C 0.0273(6) 0.5380(5) 0.48807(10) 0.0327(11) Uani 1 1 d . U . . .
H42A H -0.020214 0.476019 0.500568 0.039 Uiso 1 1 calc R U . . .
C43 C 0.0807(6) 0.6497(5) 0.50090(10) 0.0326(11) Uani 1 1 d . U . . .
C44 C 0.1477(6) 0.7434(5) 0.48332(11) 0.0352(11) Uani 1 1 d . U . . .
H44A H 0.183171 0.820019 0.491957 0.042 Uiso 1 1 calc R U . . .
C45 C 0.1606(5) 0.7205(5) 0.45247(10) 0.0281(10) Uani 1 1 d . U . . .
C46 C 0.1194(8) 0.7699(6) 0.54595(13) 0.0549(15) Uani 1 1 d . U . . .
H46A H 0.099253 0.765860 0.567733 0.082 Uiso 1 1 calc R U . . .
H46B H 0.233736 0.777122 0.542376 0.082 Uiso 1 1 calc R U . . .
H46C H 0.065316 0.843111 0.537419 0.082 Uiso 1 1 calc R U . . .
F1 F 0.4767(3) 0.4856(3) 0.41609(6) 0.0422(7) Uani 1 1 d . U . . .
N1 N 0.2521(4) 0.3846(4) 0.36975(7) 0.0264(8) Uani 1 1 d . . . . .
H1B H 0.206602 0.434028 0.383104 0.032 Uiso 1 1 calc R U . . .
N2 N 0.1530(4) 0.5069(4) 0.33003(8) 0.0258(9) Uani 1 1 d . . . . .
N3 N 0.2277(5) 0.7258(4) 0.36807(7) 0.0295(9) Uani 1 1 d . . . . .
H3B H 0.190743 0.672279 0.354667 0.035 Uiso 1 1 calc R U . . .
N4 N 0.1353(4) 0.6000(4) 0.40786(8) 0.0260(8) Uani 1 1 d . . . . .
O1 O 0.0962(5) 0.1238(4) 0.39008(10) 0.0570(11) Uani 1 1 d . . . . .
O2 O 0.0951(5) 0.4315(3) 0.20614(7) 0.0446(10) Uani 1 1 d . . . . .
O3 O 0.4402(4) 1.0297(3) 0.32266(7) 0.0371(8) Uani 1 1 d . . . . .
O4 O 0.0609(5) 0.6581(4) 0.53181(7) 0.0441(9) Uani 1 1 d . . . . .
S1 S 0.26923(14) 0.28974(11) 0.31275(2) 0.0293(3) Uani 1 1 d . . . . .
S2 S 0.23743(16) 0.82106(12) 0.42482(2) 0.0337(3) Uani 1 1 d . . . . .
C1' C 0.1831(11) 0.1913(9) 0.4757(2) 0.037(4) Uani 0.349(8) 1 d G U P A 2
H1'A H 0.268709 0.248464 0.473424 0.044 Uiso 0.349(8) 1 calc R U P A 2
C2' C 0.1272(13) 0.1615(11) 0.50432(17) 0.050(4) Uani 0.349(8) 1 d G U P A 2
H2'A H 0.174598 0.198219 0.521656 0.060 Uiso 0.349(8) 1 calc R U P A 2
C3' C 0.0019(14) 0.0779(12) 0.50760(19) 0.062(5) Uani 0.349(8) 1 d G U P A 2
H3'A H -0.036276 0.057455 0.527179 0.074 Uiso 0.349(8) 1 calc R U P A 2
C4' C -0.0674(13) 0.0241(11) 0.4822(3) 0.066(6) Uani 0.349(8) 1 d G U P A 2
H4'A H -0.153040 -0.033065 0.484471 0.079 Uiso 0.349(8) 1 calc R U P A 2
C5' C -0.0115(13) 0.0539(11) 0.4536(2) 0.057(5) Uani 0.349(8) 1 d G U P A 2
H5'A H -0.058930 0.017177 0.436239 0.068 Uiso 0.349(8) 1 calc R U P A 2
C6' C 0.1137(12) 0.1375(9) 0.45030(17) 0.020(3) Uani 0.349(8) 1 d G U P A 2
C33' C 0.4967(7) 0.8355(9) 0.3668(2) 0.028(3) Uani 0.448(14) 1 d G U P B 2
C34' C 0.5603(9) 0.9354(8) 0.3830(2) 0.035(3) Uani 0.448(14) 1 d G U P B 2
H34B H 0.493483 1.001545 0.389659 0.041 Uiso 0.448(14) 1 calc R U P B 2
C35' C 0.7216(9) 0.9385(9) 0.3893(2) 0.048(4) Uani 0.448(14) 1 d G U P B 2
H35B H 0.765063 1.006731 0.400385 0.057 Uiso 0.448(14) 1 calc R U P B 2
C36' C 0.8194(6) 0.8417(10) 0.3796(2) 0.047(4) Uani 0.448(14) 1 d G U P B 2
H36B H 0.929650 0.843806 0.383922 0.057 Uiso 0.448(14) 1 calc R U P B 2
C37' C 0.7558(9) 0.7418(9) 0.3634(2) 0.053(4) Uani 0.448(14) 1 d G U P B 2
H37B H 0.822658 0.675693 0.356732 0.063 Uiso 0.448(14) 1 calc R U P B 2
C38' C 0.5945(9) 0.7388(8) 0.3570(2) 0.034(3) Uani 0.448(14) 1 d G U P B 2
F2' F 0.549(2) 0.645(2) 0.3446(4) 0.059(5) Uani 0.2 1 d . U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 H1A 0.9500 . ?
C2 C3 1.3900 . ?
C2 H2A 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3A 0.9500 . ?
C4 C5 1.3900 . ?
C4 H4A 0.9500 . ?
C5 C6 1.3900 . ?
C5 H5A 0.9500 . ?
C6 C7 1.435(6) . ?
C7 O1 1.216(7) . ?
C7 C8 1.510(7) . ?
C7 C6' 1.714(9) . ?
C8 C9 1.527(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.466(6) . ?
C9 C10 1.520(6) . ?
C9 H9A 1.0000 . ?
C10 C15 1.387(7) . ?
C10 C11 1.389(6) . ?
C11 C12 1.383(7) . ?
C11 H11A 0.9500 . ?
C12 C13 1.391(7) . ?
C12 H12A 0.9500 . ?
C13 C14 1.376(7) . ?
C13 H13A 0.9500 . ?
C14 C15 1.373(7) . ?
C14 H14A 0.9500 . ?
C15 F1 1.372(5) . ?
C16 N2 1.315(6) . ?
C16 N1 1.346(5) . ?
C16 S1 1.775(4) . ?
C17 C18 1.387(7) . ?
C17 N2 1.403(6) . ?
C17 C22 1.409(7) . ?
C18 C19 1.394(7) . ?
C18 H18A 0.9500 . ?
C19 C20 1.391(7) . ?
C19 H19A 0.9500 . ?
C20 O2 1.382(6) . ?
C20 C21 1.397(7) . ?
C21 C22 1.389(6) . ?
C21 H21A 0.9500 . ?
C22 S1 1.748(5) . ?
C23 O2 1.413(7) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.390(7) . ?
C24 C29 1.398(7) . ?
C24 H24A 0.9500 . ?
C25 C26 1.371(8) . ?
C25 H25A 0.9500 . ?
C26 C27 1.382(8) . ?
C26 H26A 0.9500 . ?
C27 C28 1.387(7) . ?
C27 H27A 0.9500 . ?
C28 C29 1.400(7) . ?
C28 H28A 0.9500 . ?
C29 C30 1.488(6) . ?
C30 O3 1.226(6) . ?
C30 C31 1.517(7) . ?
C31 C32 1.538(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 N3 1.459(6) . ?
C32 C33 1.514(6) . ?
C32 C33' 1.565(7) . ?
C33 C34 1.3900 . ?
C33 C38 1.3900 . ?
C34 C35 1.3900 . ?
C34 H34A 0.9500 . ?
C35 C36 1.3900 . ?
C35 H35A 0.9500 . ?
C36 C37 1.3900 . ?
C36 H36A 0.9500 . ?
C37 C38 1.3900 . ?
C37 H37A 0.9500 . ?
C38 F2 1.475(8) . ?
C39 N4 1.302(6) . ?
C39 N3 1.358(5) . ?
C39 S2 1.765(5) . ?
C40 N4 1.390(6) . ?
C40 C41 1.403(7) . ?
C40 C45 1.401(7) . ?
C41 C42 1.393(7) . ?
C41 H41A 0.9500 . ?
C42 C43 1.395(7) . ?
C42 H42A 0.9500 . ?
C43 O4 1.381(6) . ?
C43 C44 1.387(7) . ?
C44 C45 1.392(7) . ?
C44 H44A 0.9500 . ?
C45 S2 1.752(5) . ?
C46 O4 1.434(7) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
N1 H1B 0.8800 . ?
N3 H3B 0.8800 . ?
C1' C2' 1.3900 . ?
C1' C6' 1.3900 . ?
C1' H1'A 0.9500 . ?
C2' C3' 1.3900 . ?
C2' H2'A 0.9500 . ?
C3' C4' 1.3900 . ?
C3' H3'A 0.9500 . ?
C4' C5' 1.3900 . ?
C4' H4'A 0.9500 . ?
C5' C6' 1.3900 . ?
C5' H5'A 0.9500 . ?
C33' C34' 1.3900 . ?
C33' C38' 1.3900 . ?
C34' C35' 1.3900 . ?
C34' H34B 0.9500 . ?
C35' C36' 1.3900 . ?
C35' H35B 0.9500 . ?
C36' C37' 1.3900 . ?
C36' H36B 0.9500 . ?
C37' C38' 1.3900 . ?
C37' H37B 0.9500 . ?
C38' F2' 1.20(2) . ?

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 C6 120.0 . . ?
C2 C1 H1A 120.0 . . ?
C6 C1 H1A 120.0 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 122.6(4) . . ?
C1 C6 C7 117.4(4) . . ?
O1 C7 C6 115.4(5) . . ?
O1 C7 C8 121.9(5) . . ?
C6 C7 C8 122.6(5) . . ?
O1 C7 C6' 130.9(6) . . ?
C8 C7 C6' 106.5(5) . . ?
C7 C8 C9 114.2(4) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N1 C9 C10 111.9(4) . . ?
N1 C9 C8 109.3(4) . . ?
C10 C9 C8 111.0(4) . . ?
N1 C9 H9A 108.2 . . ?
C10 C9 H9A 108.2 . . ?
C8 C9 H9A 108.2 . . ?
C15 C10 C11 116.8(4) . . ?
C15 C10 C9 121.6(4) . . ?
C11 C10 C9 121.6(4) . . ?
C12 C11 C10 121.0(5) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
C11 C12 C13 119.9(5) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C14 C13 C12 120.4(5) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C15 C14 C13 118.1(5) . . ?
C15 C14 H14A 120.9 . . ?
C13 C14 H14A 120.9 . . ?
C14 C15 F1 117.6(4) . . ?
C14 C15 C10 123.7(4) . . ?
F1 C15 C10 118.6(4) . . ?
N2 C16 N1 123.4(4) . . ?
N2 C16 S1 115.8(3) . . ?
N1 C16 S1 120.8(3) . . ?
C18 C17 N2 126.1(4) . . ?
C18 C17 C22 118.7(4) . . ?
N2 C17 C22 115.2(4) . . ?
C17 C18 C19 119.7(5) . . ?
C17 C18 H18A 120.2 . . ?
C19 C18 H18A 120.2 . . ?
C18 C19 C20 120.7(5) . . ?
C18 C19 H19A 119.6 . . ?
C20 C19 H19A 119.6 . . ?
O2 C20 C21 115.4(4) . . ?
O2 C20 C19 123.6(4) . . ?
C21 C20 C19 121.0(4) . . ?
C22 C21 C20 117.5(5) . . ?
C22 C21 H21A 121.3 . . ?
C20 C21 H21A 121.3 . . ?
C21 C22 C17 122.4(4) . . ?
C21 C22 S1 127.6(4) . . ?
C17 C22 S1 109.9(3) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C29 120.6(5) . . ?
C25 C24 H24A 119.7 . . ?
C29 C24 H24A 119.7 . . ?
C26 C25 C24 120.3(5) . . ?
C26 C25 H25A 119.9 . . ?
C24 C25 H25A 119.9 . . ?
C25 C26 C27 119.8(5) . . ?
C25 C26 H26A 120.1 . . ?
C27 C26 H26A 120.1 . . ?
C26 C27 C28 120.9(6) . . ?
C26 C27 H27A 119.5 . . ?
C28 C27 H27A 119.5 . . ?
C27 C28 C29 119.8(5) . . ?
C27 C28 H28A 120.1 . . ?
C29 C28 H28A 120.1 . . ?
C24 C29 C28 118.7(4) . . ?
C24 C29 C30 122.3(4) . . ?
C28 C29 C30 119.0(4) . . ?
O3 C30 C29 120.7(4) . . ?
O3 C30 C31 120.4(4) . . ?
C29 C30 C31 118.9(4) . . ?
C30 C31 C32 113.9(4) . . ?
C30 C31 H31A 108.8 . . ?
C32 C31 H31A 108.8 . . ?
C30 C31 H31B 108.8 . . ?
C32 C31 H31B 108.8 . . ?
H31A C31 H31B 107.7 . . ?
N3 C32 C33 109.7(4) . . ?
N3 C32 C31 106.2(4) . . ?
C33 C32 C31 108.3(4) . . ?
N3 C32 C33' 115.3(5) . . ?
C31 C32 C33' 115.3(5) . . ?
C34 C33 C38 120.0 . . ?
C34 C33 C32 120.0(4) . . ?
C38 C33 C32 119.9(4) . . ?
C33 C34 C35 120.0 . . ?
C33 C34 H34A 120.0 . . ?
C35 C34 H34A 120.0 . . ?
C34 C35 C36 120.0 . . ?
C34 C35 H35A 120.0 . . ?
C36 C35 H35A 120.0 . . ?
C37 C36 C35 120.0 . . ?
C37 C36 H36A 120.0 . . ?
C35 C36 H36A 120.0 . . ?
C36 C37 C38 120.0 . . ?
C36 C37 H37A 120.0 . . ?
C38 C37 H37A 120.0 . . ?
C37 C38 C33 120.0 . . ?
C37 C38 F2 121.8(4) . . ?
C33 C38 F2 118.2(4) . . ?
N4 C39 N3 123.7(4) . . ?
N4 C39 S2 116.4(3) . . ?
N3 C39 S2 119.8(3) . . ?
N4 C40 C41 125.9(4) . . ?
N4 C40 C45 115.9(4) . . ?
C41 C40 C45 118.2(4) . . ?
C42 C41 C40 119.2(5) . . ?
C42 C41 H41A 120.4 . . ?
C40 C41 H41A 120.4 . . ?
C41 C42 C43 120.9(5) . . ?
C41 C42 H42A 119.5 . . ?
C43 C42 H42A 119.5 . . ?
O4 C43 C44 123.9(5) . . ?
O4 C43 C42 114.8(4) . . ?
C44 C43 C42 121.2(4) . . ?
C45 C44 C43 117.1(5) . . ?
C45 C44 H44A 121.4 . . ?
C43 C44 H44A 121.4 . . ?
C44 C45 C40 123.3(4) . . ?
C44 C45 S2 127.4(4) . . ?
C40 C45 S2 109.3(3) . . ?
O4 C46 H46A 109.5 . . ?
O4 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
O4 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C16 N1 C9 123.5(4) . . ?
C16 N1 H1B 118.3 . . ?
C9 N1 H1B 118.3 . . ?
C16 N2 C17 110.5(4) . . ?
C39 N3 C32 123.5(4) . . ?
C39 N3 H3B 118.2 . . ?
C32 N3 H3B 118.2 . . ?
C39 N4 C40 110.1(4) . . ?
C20 O2 C23 117.0(4) . . ?
C43 O4 C46 116.4(4) . . ?
C22 S1 C16 88.7(2) . . ?
C45 S2 C39 88.3(2) . . ?
C2' C1' C6' 120.0 . . ?
C2' C1' H1'A 120.0 . . ?
C6' C1' H1'A 120.0 . . ?
C3' C2' C1' 120.0 . . ?
C3' C2' H2'A 120.0 . . ?
C1' C2' H2'A 120.0 . . ?
C2' C3' C4' 120.0 . . ?
C2' C3' H3'A 120.0 . . ?
C4' C3' H3'A 120.0 . . ?
C5' C4' C3' 120.0 . . ?
C5' C4' H4'A 120.0 . . ?
C3' C4' H4'A 120.0 . . ?
C6' C5' C4' 120.0 . . ?
C6' C5' H5'A 120.0 . . ?
C4' C5' H5'A 120.0 . . ?
C5' C6' C1' 120.0 . . ?
C5' C6' C7 111.6(6) . . ?
C1' C6' C7 128.3(6) . . ?
C34' C33' C38' 120.0 . . ?
C34' C33' C32 121.5(5) . . ?
C38' C33' C32 118.4(5) . . ?
C35' C34' C33' 120.0 . . ?
C35' C34' H34B 120.0 . . ?
C33' C34' H34B 120.0 . . ?
C36' C35' C34' 120.0 . . ?
C36' C35' H35B 120.0 . . ?
C34' C35' H35B 120.0 . . ?
C35' C36' C37' 120.0 . . ?
C35' C36' H36B 120.0 . . ?
C37' C36' H36B 120.0 . . ?
C38' C37' C36' 120.0 . . ?
C38' C37' H37B 120.0 . . ?
C36' C37' H37B 120.0 . . ?
F2' C38' C37' 115.2(11) . . ?
F2' C38' C33' 124.6(11) . . ?
C37' C38' C33' 120.0 . . ?

_refine_diff_density_max         0.547
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.054



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
