# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_F139
_database_code_depnum_ccdc_archive 'CCDC 2161058'
loop_
_audit_author_name
_audit_author_address
'Lukasz Wojtas'
;university of south florida
United States of America
;
_audit_update_record             
;
2022-03-22 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;
_audit_creation_date             2022-03-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C41 H29 N3 O5 S, C4 H8 O2, 0.916(C H2 Cl2)'
_chemical_formula_sum            'C45.92 H38.83 Cl1.83 N3 O7 S'
_chemical_formula_weight         841.72
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.6653(3)
_cell_length_b                   12.1532(3)
_cell_length_c                   16.9707(5)
_cell_angle_alpha                70.450(1)
_cell_angle_beta                 89.007(1)
_cell_angle_gamma                74.967(1)
_cell_volume                     1996.1(1)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      79.39
_cell_measurement_theta_min      4.01
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.653
_exptl_absorpt_coefficient_mu    2.327
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0776 before and 0.0537 after correction.
The Ratio of minimum to maximum transmission is 0.8335.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             877
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            40341
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.467
_diffrn_reflns_theta_min         2.771
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker PHOTON II CMOS area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec Imus'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7646
_reflns_number_total             8344
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         8344
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+1.3162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0977
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl66-C64 = Cl65-C64
 1.75 with sigma of 0.02
 Cl65-Cl66
 2.9 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C64, Cl65, Cl66
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C61)=Sof(H61A)=Sof(H61B)=Sof(Cl62)=Sof(Cl63)=FVAR(1)
 Sof(C64)=Sof(H64A)=Sof(H64B)=Sof(Cl65)=Sof(Cl66)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C52(H52A,H52B), C61(H61A,H61B), C64(H64A,H64B)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C14(H14), C16(H16), C18(H18), C24(H24),
 C30(H30), C31(H31), C32(H32), C33(H33), C34(H34), C36(H36), C37(H37), C38(H38),
  C39(H39), C40(H40), C45(H45), C46(H46), C47(H47), C48(H48), C49(H49)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C51(H51A,H51B,H51C), C56(H56A,H56B,H56C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.16706(16) 0.96507(17) 0.84207(12) 0.0304(4) Uani 1 1 d . . . . .
H1A H 0.180664 0.914502 0.901513 0.046 Uiso 1 1 calc R U . . .
H1B H 0.092992 0.952498 0.816159 0.046 Uiso 1 1 calc R U . . .
H1C H 0.149132 1.050572 0.836890 0.046 Uiso 1 1 calc R U . . .
C2 C 0.28759(15) 0.93071(14) 0.79847(10) 0.0206(3) Uani 1 1 d . . . . .
C3 C 0.39661(15) 0.84169(14) 0.84308(9) 0.0214(3) Uani 1 1 d . . . . .
H3 H 0.395493 0.803507 0.901833 0.026 Uiso 1 1 calc R U . . .
O004 O 0.52752(10) 0.59895(9) 0.73301(6) 0.0192(2) Uani 1 1 d . . . . .
C4 C 0.50744(15) 0.80741(13) 0.80327(9) 0.0188(3) Uani 1 1 d . . . . .
H4 H 0.581506 0.746079 0.834230 0.023 Uiso 1 1 calc R U . . .
C5 C 0.50797(14) 0.86432(13) 0.71759(9) 0.0159(3) Uani 1 1 d . . . . .
C6 C 0.40083(15) 0.95552(13) 0.67153(9) 0.0188(3) Uani 1 1 d . . . . .
H6 H 0.402876 0.994667 0.612976 0.023 Uiso 1 1 calc R U . . .
C7 C 0.29092(15) 0.98844(14) 0.71240(10) 0.0212(3) Uani 1 1 d . . . . .
H7 H 0.217412 1.050714 0.681586 0.025 Uiso 1 1 calc R U . . .
S8 S 0.64097(3) 0.81441(3) 0.66397(2) 0.01618(9) Uani 1 1 d . . . . .
O9 O 0.74565(10) 0.73335(11) 0.72351(7) 0.0230(2) Uani 1 1 d . . . . .
O10 O 0.66277(11) 0.91579(10) 0.59739(7) 0.0226(2) Uani 1 1 d . . . . .
N11 N 0.58412(12) 0.73709(11) 0.61528(7) 0.0158(2) Uani 1 1 d . . . . .
C12 C 0.52092(13) 0.64730(12) 0.65758(9) 0.0149(3) Uani 1 1 d . . . . .
C13 C 0.44995(13) 0.62983(12) 0.59067(8) 0.0139(3) Uani 1 1 d . . . . .
C14 C 0.37113(13) 0.55394(12) 0.59890(8) 0.0144(3) Uani 1 1 d . . . . .
H14 H 0.354588 0.505310 0.652748 0.017 Uiso 1 1 calc R U . . .
C15 C 0.31505(13) 0.54999(12) 0.52499(8) 0.0138(3) Uani 1 1 d . . . . .
C16 C 0.23157(13) 0.47453(12) 0.52982(9) 0.0148(3) Uani 1 1 d . . . . .
H16 H 0.209590 0.428250 0.582806 0.018 Uiso 1 1 calc R U . . .
C17 C 0.18263(13) 0.46882(12) 0.45720(9) 0.0142(3) Uani 1 1 d . . . . .
C18 C 0.21096(13) 0.54045(13) 0.37745(9) 0.0150(3) Uani 1 1 d . . . . .
H18 H 0.176712 0.535116 0.327953 0.018 Uiso 1 1 calc R U . . .
C19 C 0.28787(13) 0.61763(12) 0.37150(8) 0.0141(3) Uani 1 1 d . . . . .
C20 C 0.34532(13) 0.62207(12) 0.44535(8) 0.0132(3) Uani 1 1 d . . . . .
C21 C 0.43084(13) 0.69698(12) 0.43914(9) 0.0140(3) Uani 1 1 d . . . . .
C22 C 0.47732(13) 0.70267(12) 0.51257(9) 0.0140(3) Uani 1 1 d . . . . .
C23 C 0.55869(14) 0.78150(13) 0.52314(8) 0.0155(3) Uani 1 1 d . . . . .
H23A H 0.640510 0.769266 0.494857 0.019 Uiso 1 1 calc R U . . .
H23B H 0.510285 0.868358 0.501441 0.019 Uiso 1 1 calc R U . . .
C24 C 0.47475(13) 0.75130(12) 0.35768(9) 0.0150(3) Uani 1 1 d . . . . .
H24 H 0.542901 0.789702 0.353293 0.018 Uiso 1 1 calc R U . . .
C25 C 0.41985(13) 0.74784(12) 0.28820(9) 0.0151(3) Uani 1 1 d . . . . .
N26 N 0.30993(12) 0.70079(11) 0.29343(7) 0.0157(2) Uani 1 1 d . . . . .
C27 C 0.21542(14) 0.75048(14) 0.22478(9) 0.0188(3) Uani 1 1 d . . . . .
O28 O 0.14952(12) 0.69176(11) 0.20883(7) 0.0283(3) Uani 1 1 d . . . . .
C29 C 0.19437(13) 0.88259(14) 0.17513(9) 0.0175(3) Uani 1 1 d . . . . .
C30 C 0.15774(15) 0.92281(14) 0.08956(9) 0.0209(3) Uani 1 1 d . . . . .
H30 H 0.153507 0.866115 0.063093 0.025 Uiso 1 1 calc R U . . .
C31 C 0.12749(16) 1.04558(15) 0.04313(10) 0.0236(3) Uani 1 1 d . . . . .
H31 H 0.104166 1.072613 -0.015339 0.028 Uiso 1 1 calc R U . . .
C32 C 0.13113(15) 1.12903(15) 0.08160(11) 0.0246(3) Uani 1 1 d . . . . .
H32 H 0.109783 1.213064 0.049579 0.030 Uiso 1 1 calc R U . . .
C33 C 0.16601(15) 1.08978(15) 0.16702(11) 0.0253(3) Uani 1 1 d . . . . .
H33 H 0.167780 1.146970 0.193532 0.030 Uiso 1 1 calc R U . . .
C34 C 0.19822(14) 0.96694(15) 0.21349(10) 0.0216(3) Uani 1 1 d . . . . .
H34 H 0.223039 0.940121 0.271752 0.026 Uiso 1 1 calc R U . . .
C35 C 0.47644(13) 0.77720(13) 0.20573(9) 0.0158(3) Uani 1 1 d . . . . .
C36 C 0.49448(15) 0.69434(14) 0.16311(9) 0.0195(3) Uani 1 1 d . . . . .
H36 H 0.467346 0.622224 0.185960 0.023 Uiso 1 1 calc R U . . .
C37 C 0.55226(15) 0.71759(15) 0.08716(10) 0.0229(3) Uani 1 1 d . . . . .
H37 H 0.565351 0.660840 0.058556 0.027 Uiso 1 1 calc R U . . .
C38 C 0.59070(15) 0.82331(15) 0.05321(9) 0.0232(3) Uani 1 1 d . . . . .
H38 H 0.629055 0.839525 0.001045 0.028 Uiso 1 1 calc R U . . .
C39 C 0.57306(15) 0.90561(15) 0.09560(9) 0.0217(3) Uani 1 1 d . . . . .
H39 H 0.599875 0.977833 0.072372 0.026 Uiso 1 1 calc R U . . .
C40 C 0.51641(14) 0.88288(13) 0.17177(9) 0.0178(3) Uani 1 1 d . . . . .
H40 H 0.504972 0.939235 0.200609 0.021 Uiso 1 1 calc R U . . .
N41 N 0.10204(12) 0.39388(11) 0.45558(8) 0.0162(2) Uani 1 1 d . . . . .
C42 C 0.08778(14) 0.29550(13) 0.51986(9) 0.0169(3) Uani 1 1 d . . . . .
O43 O 0.14340(11) 0.26131(10) 0.58997(7) 0.0257(2) Uani 1 1 d . . . . .
C44 C -0.00014(13) 0.22834(13) 0.50004(9) 0.0168(3) Uani 1 1 d . . . . .
C45 C -0.06123(14) 0.16417(13) 0.56603(10) 0.0192(3) Uani 1 1 d . . . . .
H45 H -0.047267 0.165045 0.620926 0.023 Uiso 1 1 calc R U . . .
C46 C -0.14241(15) 0.09899(14) 0.55187(10) 0.0225(3) Uani 1 1 d . . . . .
H46 H -0.184498 0.056008 0.596978 0.027 Uiso 1 1 calc R U . . .
C47 C -0.16224(15) 0.09644(14) 0.47199(11) 0.0229(3) Uani 1 1 d . . . . .
H47 H -0.218385 0.052303 0.462288 0.027 Uiso 1 1 calc R U . . .
C48 C -0.10015(16) 0.15826(14) 0.40653(10) 0.0244(3) Uani 1 1 d . . . . .
H48 H -0.112855 0.155625 0.351996 0.029 Uiso 1 1 calc R U . . .
C49 C -0.01889(15) 0.22452(14) 0.42019(10) 0.0210(3) Uani 1 1 d . . . . .
H49 H 0.023548 0.266949 0.375034 0.025 Uiso 1 1 calc R U . . .
C51 C 0.7944(2) 0.3747(2) 0.19066(14) 0.0430(5) Uani 1 1 d . . . . .
H51A H 0.810450 0.290974 0.191985 0.064 Uiso 1 1 calc R U . . .
H51B H 0.720736 0.426676 0.150103 0.064 Uiso 1 1 calc R U . . .
H51C H 0.774305 0.378271 0.246467 0.064 Uiso 1 1 calc R U . . .
C52 C 0.9138(2) 0.41814(18) 0.16519(12) 0.0373(4) Uani 1 1 d . . . . .
H52A H 0.987418 0.368018 0.207435 0.045 Uiso 1 1 calc R U . . .
H52B H 0.937975 0.409111 0.110651 0.045 Uiso 1 1 calc R U . . .
O53 O 0.88949(13) 0.54554(12) 0.15809(8) 0.0334(3) Uani 1 1 d . . . . .
C54 C 0.90326(16) 0.56640(16) 0.22963(10) 0.0253(3) Uani 1 1 d . . . . .
O55 O 0.94640(14) 0.48731(12) 0.29518(8) 0.0361(3) Uani 1 1 d . . . . .
C56 C 0.85748(18) 0.69778(17) 0.21839(12) 0.0329(4) Uani 1 1 d . . . . .
H56A H 0.891229 0.744724 0.167788 0.049 Uiso 1 1 calc R U . . .
H56B H 0.889021 0.711516 0.267266 0.049 Uiso 1 1 calc R U . . .
H56C H 0.762089 0.723536 0.212726 0.049 Uiso 1 1 calc R U . . .
C61 C 0.2227(3) 0.5159(2) 0.10161(15) 0.0275(5) Uani 0.8409(18) 1 d . . P A 1
H61A H 0.138507 0.544727 0.123599 0.033 Uiso 0.8409(18) 1 calc R U P A 1
H61B H 0.289905 0.476786 0.149251 0.033 Uiso 0.8409(18) 1 calc R U P A 1
Cl62 Cl 0.21013(5) 0.40924(4) 0.05417(3) 0.02732(15) Uani 0.8409(18) 1 d . . P
A 1
Cl63 Cl 0.26432(10) 0.63953(6) 0.02810(4) 0.0562(2) Uani 0.8409(18) 1 d . . P A
1
C64 C 0.276(2) 0.532(3) 0.0950(14) 0.046(9) Uani 0.075(2) 1 d D . P B 2
H64A H 0.247560 0.457099 0.119714 0.055 Uiso 0.075(2) 1 calc R U P B 2
H64B H 0.296861 0.558265 0.141336 0.055 Uiso 0.075(2) 1 calc R U P B 2
Cl65 Cl 0.4157(8) 0.5016(7) 0.0412(5) 0.051(2) Uani 0.075(2) 1 d D . P B 2
Cl66 Cl 0.1508(14) 0.6439(12) 0.0285(8) 0.092(4) Uani 0.075(2) 1 d D . P B 2
H41 H 0.056(2) 0.4146(18) 0.4119(13) 0.024(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.506(2) . ?
C2 C3 1.388(2) . ?
C2 C7 1.397(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(2) . ?
O004 C12 1.2112(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(2) . ?
C5 C6 1.393(2) . ?
C5 S8 1.7568(14) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(2) . ?
C7 H7 0.9500 . ?
S8 O9 1.4284(11) . ?
S8 O10 1.4341(11) . ?
S8 N11 1.6631(12) . ?
N11 C12 1.4145(18) . ?
N11 C23 1.4778(17) . ?
C12 C13 1.4772(19) . ?
C13 C14 1.3743(19) . ?
C13 C22 1.4004(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.4193(19) . ?
C15 C16 1.4182(19) . ?
C15 C20 1.4274(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.3765(19) . ?
C17 C18 1.4194(19) . ?
C17 N41 1.4115(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.377(2) . ?
C19 C20 1.4276(19) . ?
C19 N26 1.4314(17) . ?
C20 C21 1.4266(19) . ?
C21 C22 1.3785(19) . ?
C21 C24 1.4469(19) . ?
C22 C23 1.5016(19) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24 0.9500 . ?
C24 C25 1.3435(19) . ?
C25 N26 1.4211(18) . ?
C25 C35 1.4827(19) . ?
N26 C27 1.4113(18) . ?
C27 O28 1.2136(19) . ?
C27 C29 1.501(2) . ?
C29 C30 1.395(2) . ?
C29 C34 1.395(2) . ?
C30 H30 0.9500 . ?
C30 C31 1.387(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.386(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.390(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.387(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.399(2) . ?
C35 C40 1.394(2) . ?
C36 H36 0.9500 . ?
C36 C37 1.393(2) . ?
C37 H37 0.9500 . ?
C37 C38 1.386(2) . ?
C38 H38 0.9500 . ?
C38 C39 1.390(2) . ?
C39 H39 0.9500 . ?
C39 C40 1.390(2) . ?
C40 H40 0.9500 . ?
N41 C42 1.3632(19) . ?
N41 H41 0.83(2) . ?
C42 O43 1.2272(18) . ?
C42 C44 1.5001(19) . ?
C44 C45 1.393(2) . ?
C44 C49 1.391(2) . ?
C45 H45 0.9500 . ?
C45 C46 1.387(2) . ?
C46 H46 0.9500 . ?
C46 C47 1.388(2) . ?
C47 H47 0.9500 . ?
C47 C48 1.382(2) . ?
C48 H48 0.9500 . ?
C48 C49 1.395(2) . ?
C49 H49 0.9500 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C51 C52 1.505(3) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C52 O53 1.465(2) . ?
O53 C54 1.338(2) . ?
C54 O55 1.203(2) . ?
C54 C56 1.490(2) . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C61 Cl62 1.772(2) . ?
C61 Cl63 1.756(2) . ?
C64 H64A 0.9900 . ?
C64 H64B 0.9900 . ?
C64 Cl65 1.757(18) . ?
C64 Cl66 1.728(18) . ?
Cl65 Cl65 2.259(17) 2_665 ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 120.59(15) . . ?
C3 C2 C7 119.15(14) . . ?
C7 C2 C1 120.26(15) . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.13(14) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.82(14) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 121.27(13) . . ?
C4 C5 S8 119.90(11) . . ?
C6 C5 S8 118.69(11) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.07(14) . . ?
C7 C6 H6 120.5 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.55(14) . . ?
C6 C7 H7 119.7 . . ?
O9 S8 C5 109.21(7) . . ?
O9 S8 O10 120.10(7) . . ?
O9 S8 N11 109.05(6) . . ?
O10 S8 C5 109.72(7) . . ?
O10 S8 N11 104.38(6) . . ?
N11 S8 C5 102.94(6) . . ?
C12 N11 S8 122.24(9) . . ?
C12 N11 C23 113.42(11) . . ?
C23 N11 S8 121.75(9) . . ?
O004 C12 N11 124.60(13) . . ?
O004 C12 C13 130.27(13) . . ?
N11 C12 C13 105.13(11) . . ?
C14 C13 C12 128.22(13) . . ?
C14 C13 C22 122.69(13) . . ?
C22 C13 C12 109.07(12) . . ?
C13 C14 H14 120.8 . . ?
C13 C14 C15 118.38(12) . . ?
C15 C14 H14 120.8 . . ?
C14 C15 C20 118.98(12) . . ?
C16 C15 C14 120.75(12) . . ?
C16 C15 C20 120.27(12) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.54(13) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 120.94(13) . . ?
C16 C17 N41 123.75(13) . . ?
N41 C17 C18 115.31(12) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.29(12) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C20 120.43(12) . . ?
C18 C19 N26 123.15(12) . . ?
C20 C19 N26 116.35(12) . . ?
C15 C20 C19 118.41(12) . . ?
C21 C20 C15 121.14(12) . . ?
C21 C20 C19 120.45(12) . . ?
C20 C21 C24 118.14(12) . . ?
C22 C21 C20 117.67(12) . . ?
C22 C21 C24 123.82(13) . . ?
C13 C22 C23 110.73(12) . . ?
C21 C22 C13 120.97(13) . . ?
C21 C22 C23 128.30(13) . . ?
N11 C23 C22 101.39(11) . . ?
N11 C23 H23A 111.5 . . ?
N11 C23 H23B 111.5 . . ?
C22 C23 H23A 111.5 . . ?
C22 C23 H23B 111.5 . . ?
H23A C23 H23B 109.3 . . ?
C21 C24 H24 119.8 . . ?
C25 C24 C21 120.49(13) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 N26 119.94(12) . . ?
C24 C25 C35 123.59(13) . . ?
N26 C25 C35 116.07(12) . . ?
C25 N26 C19 119.53(11) . . ?
C27 N26 C19 121.19(12) . . ?
C27 N26 C25 118.65(12) . . ?
N26 C27 C29 116.52(12) . . ?
O28 C27 N26 122.16(14) . . ?
O28 C27 C29 121.22(13) . . ?
C30 C29 C27 118.48(13) . . ?
C34 C29 C27 121.80(13) . . ?
C34 C29 C30 119.43(14) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 119.99(14) . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 119.8 . . ?
C32 C31 C30 120.34(15) . . ?
C32 C31 H31 119.8 . . ?
C31 C32 H32 120.0 . . ?
C31 C32 C33 120.00(15) . . ?
C33 C32 H32 120.0 . . ?
C32 C33 H33 120.1 . . ?
C34 C33 C32 119.89(15) . . ?
C34 C33 H33 120.1 . . ?
C29 C34 H34 119.8 . . ?
C33 C34 C29 120.35(14) . . ?
C33 C34 H34 119.8 . . ?
C36 C35 C25 118.90(13) . . ?
C40 C35 C25 121.37(13) . . ?
C40 C35 C36 119.68(13) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 C35 119.98(14) . . ?
C37 C36 H36 120.0 . . ?
C36 C37 H37 119.9 . . ?
C38 C37 C36 120.15(14) . . ?
C38 C37 H37 119.9 . . ?
C37 C38 H38 120.0 . . ?
C37 C38 C39 119.91(14) . . ?
C39 C38 H38 120.0 . . ?
C38 C39 H39 119.8 . . ?
C38 C39 C40 120.42(14) . . ?
C40 C39 H39 119.8 . . ?
C35 C40 H40 120.1 . . ?
C39 C40 C35 119.85(14) . . ?
C39 C40 H40 120.1 . . ?
C17 N41 H41 116.1(14) . . ?
C42 N41 C17 126.87(12) . . ?
C42 N41 H41 117.0(14) . . ?
N41 C42 C44 115.94(13) . . ?
O43 C42 N41 123.25(13) . . ?
O43 C42 C44 120.81(13) . . ?
C45 C44 C42 117.53(13) . . ?
C49 C44 C42 122.90(13) . . ?
C49 C44 C45 119.54(13) . . ?
C44 C45 H45 119.9 . . ?
C46 C45 C44 120.24(14) . . ?
C46 C45 H45 119.9 . . ?
C45 C46 H46 119.9 . . ?
C45 C46 C47 120.15(14) . . ?
C47 C46 H46 119.9 . . ?
C46 C47 H47 120.1 . . ?
C48 C47 C46 119.87(14) . . ?
C48 C47 H47 120.1 . . ?
C47 C48 H48 119.8 . . ?
C47 C48 C49 120.32(15) . . ?
C49 C48 H48 119.8 . . ?
C44 C49 C48 119.87(14) . . ?
C44 C49 H49 120.1 . . ?
C48 C49 H49 120.1 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C52 C51 H51A 109.5 . . ?
C52 C51 H51B 109.5 . . ?
C52 C51 H51C 109.5 . . ?
C51 C52 H52A 109.6 . . ?
C51 C52 H52B 109.6 . . ?
H52A C52 H52B 108.1 . . ?
O53 C52 C51 110.39(16) . . ?
O53 C52 H52A 109.6 . . ?
O53 C52 H52B 109.6 . . ?
C54 O53 C52 116.11(14) . . ?
O53 C54 C56 112.16(14) . . ?
O55 C54 O53 123.33(16) . . ?
O55 C54 C56 124.50(16) . . ?
C54 C56 H56A 109.5 . . ?
C54 C56 H56B 109.5 . . ?
C54 C56 H56C 109.5 . . ?
H56A C56 H56B 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
H61A C61 H61B 108.1 . . ?
Cl62 C61 H61A 109.6 . . ?
Cl62 C61 H61B 109.6 . . ?
Cl63 C61 H61A 109.6 . . ?
Cl63 C61 H61B 109.6 . . ?
Cl63 C61 Cl62 110.14(14) . . ?
H64A C64 H64B 108.0 . . ?
Cl65 C64 H64A 109.4 . . ?
Cl65 C64 H64B 109.4 . . ?
Cl66 C64 H64A 109.4 . . ?
Cl66 C64 H64B 109.4 . . ?
Cl66 C64 Cl65 111.1(14) . . ?
C64 Cl65 Cl65 169.7(12) . 2_665 ?

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 C2 C3 C4 178.66(14) . . . . ?
C1 C2 C7 C6 -178.73(14) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C2 C7 C6 1.4(2) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
C3 C4 C5 S8 -174.65(11) . . . . ?
O004 C12 C13 C14 1.2(2) . . . . ?
O004 C12 C13 C22 -177.22(14) . . . . ?
C4 C5 C6 C7 -0.9(2) . . . . ?
C4 C5 S8 O9 -12.05(14) . . . . ?
C4 C5 S8 O10 -145.61(11) . . . . ?
C4 C5 S8 N11 103.71(12) . . . . ?
C5 C6 C7 C2 -0.2(2) . . . . ?
C5 S8 N11 C12 -49.70(13) . . . . ?
C5 S8 N11 C23 110.82(11) . . . . ?
C6 C5 S8 O9 172.31(11) . . . . ?
C6 C5 S8 O10 38.75(13) . . . . ?
C6 C5 S8 N11 -71.92(12) . . . . ?
C7 C2 C3 C4 -1.4(2) . . . . ?
S8 C5 C6 C7 174.63(11) . . . . ?
S8 N11 C12 O004 -17.5(2) . . . . ?
S8 N11 C12 C13 162.31(10) . . . . ?
S8 N11 C23 C22 -165.24(9) . . . . ?
O9 S8 N11 C12 66.18(13) . . . . ?
O9 S8 N11 C23 -133.29(11) . . . . ?
O10 S8 N11 C12 -164.30(11) . . . . ?
O10 S8 N11 C23 -3.78(13) . . . . ?
N11 C12 C13 C14 -178.61(13) . . . . ?
N11 C12 C13 C22 2.98(15) . . . . ?
C12 N11 C23 C22 -3.14(15) . . . . ?
C12 C13 C14 C15 -178.47(13) . . . . ?
C12 C13 C22 C21 175.22(12) . . . . ?
C12 C13 C22 C23 -5.15(15) . . . . ?
C13 C14 C15 C16 -179.15(12) . . . . ?
C13 C14 C15 C20 1.69(19) . . . . ?
C13 C22 C23 N11 4.98(14) . . . . ?
C14 C13 C22 C21 -3.3(2) . . . . ?
C14 C13 C22 C23 176.34(12) . . . . ?
C14 C15 C16 C17 -177.45(13) . . . . ?
C14 C15 C20 C19 -179.76(12) . . . . ?
C14 C15 C20 C21 0.25(19) . . . . ?
C15 C16 C17 C18 -2.1(2) . . . . ?
C15 C16 C17 N41 178.08(12) . . . . ?
C15 C20 C21 C22 -3.62(19) . . . . ?
C15 C20 C21 C24 169.66(12) . . . . ?
C16 C15 C20 C19 1.08(19) . . . . ?
C16 C15 C20 C21 -178.91(12) . . . . ?
C16 C17 C18 C19 -0.3(2) . . . . ?
C16 C17 N41 C42 -18.8(2) . . . . ?
C17 C18 C19 C20 3.2(2) . . . . ?
C17 C18 C19 N26 -173.75(12) . . . . ?
C17 N41 C42 O43 1.9(2) . . . . ?
C17 N41 C42 C44 -177.36(12) . . . . ?
C18 C17 N41 C42 161.42(13) . . . . ?
C18 C19 C20 C15 -3.51(19) . . . . ?
C18 C19 C20 C21 176.48(13) . . . . ?
C18 C19 N26 C25 -159.60(13) . . . . ?
C18 C19 N26 C27 29.6(2) . . . . ?
C19 C20 C21 C22 176.39(12) . . . . ?
C19 C20 C21 C24 -10.33(19) . . . . ?
C19 N26 C27 O28 -37.7(2) . . . . ?
C19 N26 C27 C29 138.61(13) . . . . ?
C20 C15 C16 C17 1.7(2) . . . . ?
C20 C19 N26 C25 23.38(18) . . . . ?
C20 C19 N26 C27 -147.46(13) . . . . ?
C20 C21 C22 C13 5.09(19) . . . . ?
C20 C21 C22 C23 -174.47(13) . . . . ?
C20 C21 C24 C25 10.9(2) . . . . ?
C21 C22 C23 N11 -175.41(13) . . . . ?
C21 C24 C25 N26 5.9(2) . . . . ?
C21 C24 C25 C35 -166.50(13) . . . . ?
C22 C13 C14 C15 -0.3(2) . . . . ?
C22 C21 C24 C25 -176.30(13) . . . . ?
C23 N11 C12 O004 -179.51(13) . . . . ?
C23 N11 C12 C13 0.31(15) . . . . ?
C24 C21 C22 C13 -167.77(13) . . . . ?
C24 C21 C22 C23 12.7(2) . . . . ?
C24 C25 N26 C19 -23.68(19) . . . . ?
C24 C25 N26 C27 147.38(14) . . . . ?
C24 C25 C35 C36 127.90(16) . . . . ?
C24 C25 C35 C40 -49.5(2) . . . . ?
C25 N26 C27 O28 151.34(14) . . . . ?
C25 N26 C27 C29 -32.31(18) . . . . ?
C25 C35 C36 C37 -177.42(13) . . . . ?
C25 C35 C40 C39 177.86(13) . . . . ?
N26 C19 C20 C15 173.60(12) . . . . ?
N26 C19 C20 C21 -6.41(19) . . . . ?
N26 C25 C35 C36 -44.79(18) . . . . ?
N26 C25 C35 C40 137.77(14) . . . . ?
N26 C27 C29 C30 148.61(13) . . . . ?
N26 C27 C29 C34 -37.6(2) . . . . ?
C27 C29 C30 C31 174.91(14) . . . . ?
C27 C29 C34 C33 -173.75(14) . . . . ?
O28 C27 C29 C30 -35.0(2) . . . . ?
O28 C27 C29 C34 138.77(16) . . . . ?
C29 C30 C31 C32 -1.2(2) . . . . ?
C30 C29 C34 C33 0.0(2) . . . . ?
C30 C31 C32 C33 0.4(2) . . . . ?
C31 C32 C33 C34 0.6(2) . . . . ?
C32 C33 C34 C29 -0.7(2) . . . . ?
C34 C29 C30 C31 1.0(2) . . . . ?
C35 C25 N26 C19 149.30(12) . . . . ?
C35 C25 N26 C27 -39.64(18) . . . . ?
C35 C36 C37 C38 -0.7(2) . . . . ?
C36 C35 C40 C39 0.4(2) . . . . ?
C36 C37 C38 C39 0.8(2) . . . . ?
C37 C38 C39 C40 -0.3(2) . . . . ?
C38 C39 C40 C35 -0.3(2) . . . . ?
C40 C35 C36 C37 0.1(2) . . . . ?
N41 C17 C18 C19 179.51(12) . . . . ?
N41 C42 C44 C45 -153.40(13) . . . . ?
N41 C42 C44 C49 28.9(2) . . . . ?
C42 C44 C45 C46 -179.18(13) . . . . ?
C42 C44 C49 C48 178.73(14) . . . . ?
O43 C42 C44 C45 27.3(2) . . . . ?
O43 C42 C44 C49 -150.42(15) . . . . ?
C44 C45 C46 C47 0.6(2) . . . . ?
C45 C44 C49 C48 1.0(2) . . . . ?
C45 C46 C47 C48 0.5(2) . . . . ?
C46 C47 C48 C49 -0.8(2) . . . . ?
C47 C48 C49 C44 0.1(2) . . . . ?
C49 C44 C45 C46 -1.4(2) . . . . ?
C51 C52 O53 C54 83.03(19) . . . . ?
C52 O53 C54 O55 7.9(2) . . . . ?
C52 O53 C54 C56 -171.37(15) . . . . ?
Cl66 C64 Cl65 Cl65 35(9) . . . 2_665 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_F89
_database_code_depnum_ccdc_archive 'CCDC 2161061'
loop_
_audit_author_name
_audit_author_address
'Lukasz Wojtas'
;university of south florida
United States of America
;
_audit_update_record             
;
2022-03-22 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;
_audit_creation_date             2022-03-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 O2'
_chemical_formula_sum            'C20 H12 O2'
_chemical_formula_weight         284.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.0281(2)
_cell_length_b                   5.29640(10)
_cell_length_c                   16.7488(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.9850(10)
_cell_angle_gamma                90
_cell_volume                     1400.29(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9350
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      80.04
_cell_measurement_theta_min      5.36
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    0.690
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1304 before and 0.0601 after correction.
The Ratio of minimum to maximum transmission is 0.8525.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26828
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.050
_diffrn_reflns_theta_min         2.799
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker PHOTON II CMOS area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon-II CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec Imus'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2728
_reflns_number_total             3037
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3037
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0539P)²+0.3921P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0989
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C21(H21), C5(H5), C7(H7), C6(H6), C25(H25), C1(H1), C34(H34),
 C32(H32), C30(H30)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O8 O 0.54787(5) 1.17806(14) 0.28482(4) 0.02075(18) Uani 1 1 d . . . . .
O9 O 0.46153(5) 1.14839(16) 0.37679(5) 0.0265(2) Uani 1 1 d . . . . .
C11 C 0.70381(6) 0.66711(18) 0.34029(6) 0.0168(2) Uani 1 1 d . . . . .
C12 C 0.58329(6) 0.7130(2) 0.44659(6) 0.0185(2) Uani 1 1 d . . . . .
H12 H 0.543012 0.732789 0.481585 0.022 Uiso 1 1 calc R U . . .
C14 C 0.64020(6) 0.84553(19) 0.32778(6) 0.0169(2) Uani 1 1 d . . . . .
C15 C 0.87566(6) 0.65271(19) 0.18792(6) 0.0173(2) Uani 1 1 d . . . . .
C16 C 0.70777(6) 0.50100(19) 0.40865(6) 0.0173(2) Uani 1 1 d . . . . .
C17 C 0.76447(6) 0.65363(19) 0.28696(6) 0.0188(2) Uani 1 1 d . . . . .
C18 C 0.58109(6) 0.86424(19) 0.37995(6) 0.0178(2) Uani 1 1 d . . . . .
C19 C 0.64728(6) 0.5264(2) 0.46186(6) 0.0178(2) Uani 1 1 d . . . . .
C20 C 0.81451(6) 0.64977(19) 0.24124(6) 0.0190(2) Uani 1 1 d . . . . .
C21 C 0.99701(7) 0.6674(2) 0.08703(6) 0.0214(2) Uani 1 1 d . . . . .
H21 H 1.038681 0.673633 0.053077 0.026 Uiso 1 1 calc R U . . .
C23 C 0.62002(6) 1.04396(19) 0.26362(6) 0.0187(2) Uani 1 1 d . . . . .
H23A H 0.668691 1.159341 0.264043 0.022 Uiso 1 1 calc R U . . .
H23B H 0.605365 0.966318 0.209221 0.022 Uiso 1 1 calc R U . . .
C10 C 0.52246(7) 1.0718(2) 0.35067(6) 0.0197(2) Uani 1 1 d . . . . .
C5 C 0.93817(7) 0.4657(2) 0.19377(6) 0.0198(2) Uani 1 1 d . . . . .
H5 H 0.939424 0.333332 0.232243 0.024 Uiso 1 1 calc R U . . .
C7 C 0.87393(7) 0.8453(2) 0.13053(7) 0.0210(2) Uani 1 1 d . . . . .
H7 H 0.831303 0.971713 0.125730 0.025 Uiso 1 1 calc R U . . .
C6 C 0.65223(7) 0.3602(2) 0.52916(6) 0.0206(2) Uani 1 1 d . . . . .
H6 H 0.612910 0.377641 0.565221 0.025 Uiso 1 1 calc R U . . .
C25 C 0.77013(6) 0.3097(2) 0.42535(6) 0.0203(2) Uani 1 1 d . . . . .
H25 H 0.811010 0.291205 0.390919 0.024 Uiso 1 1 calc R U . . .
C1 C 0.71278(7) 0.1752(2) 0.54287(6) 0.0225(2) Uani 1 1 d . . . . .
H1 H 0.714627 0.063766 0.587580 0.027 Uiso 1 1 calc R U . . .
C34 C 0.99842(7) 0.4738(2) 0.14324(6) 0.0216(2) Uani 1 1 d . . . . .
H34 H 1.040699 0.346478 0.147166 0.026 Uiso 1 1 calc R U . . .
C32 C 0.93459(7) 0.8516(2) 0.08058(7) 0.0232(2) Uani 1 1 d . . . . .
H32 H 0.933367 0.982826 0.041729 0.028 Uiso 1 1 calc R U . . .
C30 C 0.77253(7) 0.1506(2) 0.49034(7) 0.0226(2) Uani 1 1 d . . . . .
H30 H 0.814665 0.022783 0.500145 0.027 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
O8 C23 1.4527(12) . ?
O8 C10 1.3619(13) . ?
O9 C10 1.2074(13) . ?
C11 C14 1.3793(14) . ?
C11 C16 1.4367(14) . ?
C11 C17 1.4315(14) . ?
C12 H12 0.9500 . ?
C12 C18 1.3693(14) . ?
C12 C19 1.4152(14) . ?
C14 C18 1.3993(14) . ?
C14 C23 1.4978(14) . ?
C15 C20 1.4359(14) . ?
C15 C5 1.4002(14) . ?
C15 C7 1.3986(14) . ?
C16 C19 1.4324(14) . ?
C16 C25 1.4168(14) . ?
C17 C20 1.2012(15) . ?
C18 C10 1.4738(14) . ?
C19 C6 1.4218(14) . ?
C21 H21 0.9500 . ?
C21 C34 1.3895(15) . ?
C21 C32 1.3882(16) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C5 H5 0.9500 . ?
C5 C34 1.3908(14) . ?
C7 H7 0.9500 . ?
C7 C32 1.3887(15) . ?
C6 H6 0.9500 . ?
C6 C1 1.3699(15) . ?
C25 H25 0.9500 . ?
C25 C30 1.3718(15) . ?
C1 H1 0.9500 . ?
C1 C30 1.4145(16) . ?
C34 H34 0.9500 . ?
C32 H32 0.9500 . ?
C30 H30 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O8 C23 111.00(8) . . ?
C14 C11 C16 118.03(9) . . ?
C14 C11 C17 120.23(9) . . ?
C17 C11 C16 121.73(9) . . ?
C18 C12 H12 120.9 . . ?
C18 C12 C19 118.11(9) . . ?
C19 C12 H12 120.9 . . ?
C11 C14 C18 121.09(9) . . ?
C11 C14 C23 130.67(9) . . ?
C18 C14 C23 108.24(9) . . ?
C5 C15 C20 120.41(9) . . ?
C7 C15 C20 120.07(9) . . ?
C7 C15 C5 119.52(9) . . ?
C19 C16 C11 119.81(9) . . ?
C25 C16 C11 121.83(9) . . ?
C25 C16 C19 118.35(9) . . ?
C20 C17 C11 177.90(11) . . ?
C12 C18 C14 122.89(9) . . ?
C12 C18 C10 129.22(9) . . ?
C14 C18 C10 107.86(9) . . ?
C12 C19 C16 120.05(9) . . ?
C12 C19 C6 120.98(9) . . ?
C6 C19 C16 118.96(9) . . ?
C17 C20 C15 178.05(11) . . ?
C34 C21 H21 120.1 . . ?
C32 C21 H21 120.1 . . ?
C32 C21 C34 119.89(10) . . ?
O8 C23 C14 104.46(8) . . ?
O8 C23 H23A 110.9 . . ?
O8 C23 H23B 110.9 . . ?
C14 C23 H23A 110.9 . . ?
C14 C23 H23B 110.9 . . ?
H23A C23 H23B 108.9 . . ?
O8 C10 C18 108.35(8) . . ?
O9 C10 O8 121.92(10) . . ?
O9 C10 C18 129.73(10) . . ?
C15 C5 H5 120.0 . . ?
C34 C5 C15 119.98(10) . . ?
C34 C5 H5 120.0 . . ?
C15 C7 H7 120.0 . . ?
C32 C7 C15 119.94(10) . . ?
C32 C7 H7 120.0 . . ?
C19 C6 H6 119.5 . . ?
C1 C6 C19 121.08(10) . . ?
C1 C6 H6 119.5 . . ?
C16 C25 H25 119.4 . . ?
C30 C25 C16 121.18(10) . . ?
C30 C25 H25 119.4 . . ?
C6 C1 H1 120.1 . . ?
C6 C1 C30 119.88(10) . . ?
C30 C1 H1 120.1 . . ?
C21 C34 C5 120.23(10) . . ?
C21 C34 H34 119.9 . . ?
C5 C34 H34 119.9 . . ?
C21 C32 C7 120.44(10) . . ?
C21 C32 H32 119.8 . . ?
C7 C32 H32 119.8 . . ?
C25 C30 C1 120.52(10) . . ?
C25 C30 H30 119.7 . . ?
C1 C30 H30 119.7 . . ?

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
C11 C14 C18 C12 1.31(15) . . . . ?
C11 C14 C18 C10 179.69(9) . . . . ?
C11 C14 C23 O8 -177.89(10) . . . . ?
C11 C16 C19 C12 0.65(14) . . . . ?
C11 C16 C19 C6 179.98(9) . . . . ?
C11 C16 C25 C30 -179.25(9) . . . . ?
C12 C18 C10 O8 176.28(10) . . . . ?
C12 C18 C10 O9 -3.27(19) . . . . ?
C12 C19 C6 C1 178.31(10) . . . . ?
C14 C11 C16 C19 -0.80(14) . . . . ?
C14 C11 C16 C25 178.97(9) . . . . ?
C14 C18 C10 O8 -1.97(11) . . . . ?
C14 C18 C10 O9 178.48(11) . . . . ?
C15 C5 C34 C21 0.18(15) . . . . ?
C15 C7 C32 C21 0.15(16) . . . . ?
C16 C11 C14 C18 -0.13(14) . . . . ?
C16 C11 C14 C23 179.34(9) . . . . ?
C16 C19 C6 C1 -1.01(15) . . . . ?
C16 C25 C30 C1 -0.46(16) . . . . ?
C17 C11 C14 C18 -179.02(9) . . . . ?
C17 C11 C14 C23 0.46(16) . . . . ?
C17 C11 C16 C19 178.07(9) . . . . ?
C17 C11 C16 C25 -2.16(15) . . . . ?
C18 C12 C19 C16 0.45(14) . . . . ?
C18 C12 C19 C6 -178.86(9) . . . . ?
C18 C14 C23 O8 1.63(10) . . . . ?
C19 C12 C18 C14 -1.44(15) . . . . ?
C19 C12 C18 C10 -179.46(10) . . . . ?
C19 C16 C25 C30 0.53(15) . . . . ?
C19 C6 C1 C30 1.10(15) . . . . ?
C20 C15 C5 C34 -178.37(9) . . . . ?
C20 C15 C7 C32 178.21(9) . . . . ?
C23 O8 C10 O9 -177.31(9) . . . . ?
C23 O8 C10 C18 3.10(11) . . . . ?
C23 C14 C18 C12 -178.27(9) . . . . ?
C23 C14 C18 C10 0.11(11) . . . . ?
C10 O8 C23 C14 -2.95(10) . . . . ?
C5 C15 C7 C32 -0.78(15) . . . . ?
C7 C15 C5 C34 0.61(15) . . . . ?
C6 C1 C30 C25 -0.36(16) . . . . ?
C25 C16 C19 C12 -179.13(9) . . . . ?
C25 C16 C19 C6 0.19(14) . . . . ?
C34 C21 C32 C7 0.65(16) . . . . ?
C32 C21 C34 C5 -0.82(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_f111
_database_code_depnum_ccdc_archive 'CCDC 2161060'
loop_
_audit_author_name
_audit_author_address
'Lukasz Wojtas'
;university of south florida
United States of America
;
_audit_update_record             
;
2022-03-22 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;
_audit_creation_date             2022-03-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H17 Br F N O3 S'
_chemical_formula_sum            'C27 H17 Br F N O3 S'
_chemical_formula_weight         534.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9493(2)
_cell_length_b                   24.1157(5)
_cell_length_c                   11.4002(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.3000(10)
_cell_angle_gamma                90
_cell_volume                     2184.89(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      79.17
_cell_measurement_theta_min      3.67
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.516
_exptl_absorpt_coefficient_mu    3.806
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.5499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1031 before and 0.0682 after correction.
The Ratio of minimum to maximum transmission is 0.7290.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            52092
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.586
_diffrn_reflns_theta_min         3.666
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker PHOTON II CMOS area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec Imus'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4213
_reflns_number_total             4705
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4705
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+1.9627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0733
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C21(H21), C22(H22), C24(H24), C25(H25), C30(H30),
 C31(H31), C32(H32), C33(H33), C34(H34)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.86690(3) 0.61587(2) 0.68875(2) 0.02654(7) Uani 1 1 d . . . . .
C2 C 0.7628(2) 0.59741(8) 0.54242(16) 0.0201(4) Uani 1 1 d . . . . .
C3 C 0.7087(2) 0.64189(8) 0.47689(17) 0.0238(4) Uani 1 1 d . . . . .
H3 H 0.729137 0.678388 0.505142 0.029 Uiso 1 1 calc R U . . .
C4 C 0.6233(2) 0.63442(8) 0.36831(17) 0.0244(4) Uani 1 1 d . . . . .
H4 H 0.588243 0.665235 0.321947 0.029 Uiso 1 1 calc R U . . .
C5 C 0.5931(2) 0.58181(8) 0.33249(16) 0.0216(4) Uani 1 1 d . . . . .
C6 C 0.6491(2) 0.53408(8) 0.39412(15) 0.0183(3) Uani 1 1 d . . . . .
C7 C 0.6185(2) 0.48114(8) 0.34557(15) 0.0180(3) Uani 1 1 d . . . . .
H7 H 0.558062 0.477005 0.273258 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6785(2) 0.43594(8) 0.40568(15) 0.0180(3) Uani 1 1 d . . . . .
C9 C 0.6705(2) 0.37679(8) 0.37154(16) 0.0195(4) Uani 1 1 d . . . . .
N10 N 0.7498(2) 0.34830(6) 0.46474(13) 0.0204(3) Uani 1 1 d . . . . .
C11 C 0.8156(2) 0.38513(8) 0.55900(15) 0.0192(4) Uani 1 1 d . . . . .
H11A H 0.939311 0.381818 0.568608 0.023 Uiso 1 1 calc R U . . .
H11B H 0.762417 0.377144 0.634834 0.023 Uiso 1 1 calc R U . . .
C12 C 0.7655(2) 0.44131(8) 0.51280(15) 0.0181(3) Uani 1 1 d . . . . .
C13 C 0.8000(2) 0.49232(8) 0.56391(15) 0.0183(3) Uani 1 1 d . . . . .
C14 C 0.7397(2) 0.54127(8) 0.50406(15) 0.0177(3) Uani 1 1 d . . . . .
F15 F 0.50492(15) 0.57317(5) 0.23123(10) 0.0260(2) Uani 1 1 d . . . . .
O16 O 0.61088(17) 0.35615(6) 0.28330(11) 0.0240(3) Uani 1 1 d . . . . .
S17 S 0.78947(6) 0.28029(2) 0.46491(4) 0.02148(10) Uani 1 1 d . . . . .
O18 O 0.86514(19) 0.26607(6) 0.35624(12) 0.0275(3) Uani 1 1 d . . . . .
O19 O 0.87828(18) 0.27148(6) 0.57388(12) 0.0263(3) Uani 1 1 d . . . . .
C20 C 0.5915(2) 0.24826(8) 0.46922(16) 0.0218(4) Uani 1 1 d . . . . .
C21 C 0.4999(3) 0.23914(8) 0.36541(17) 0.0249(4) Uani 1 1 d . . . . .
H21 H 0.542115 0.250911 0.292212 0.030 Uiso 1 1 calc R U . . .
C22 C 0.3456(3) 0.21250(8) 0.37122(17) 0.0257(4) Uani 1 1 d . . . . .
H22 H 0.281338 0.206560 0.301089 0.031 Uiso 1 1 calc R U . . .
C23 C 0.2828(3) 0.19423(8) 0.47789(17) 0.0240(4) Uani 1 1 d . . . . .
C24 C 0.3771(3) 0.20444(8) 0.58105(16) 0.0233(4) Uani 1 1 d . . . . .
H24 H 0.334789 0.192805 0.654329 0.028 Uiso 1 1 calc R U . . .
C25 C 0.5307(3) 0.23118(8) 0.57774(16) 0.0226(4) Uani 1 1 d . . . . .
H25 H 0.594058 0.237871 0.647973 0.027 Uiso 1 1 calc R U . . .
C26 C 0.1192(3) 0.16315(9) 0.4825(2) 0.0306(4) Uani 1 1 d . . . . .
H26A H 0.050434 0.171699 0.412368 0.046 Uiso 1 1 calc R U . . .
H26B H 0.058627 0.174271 0.552653 0.046 Uiso 1 1 calc R U . . .
H26C H 0.141718 0.123219 0.485499 0.046 Uiso 1 1 calc R U . . .
C27 C 0.8983(2) 0.49057(8) 0.67011(16) 0.0205(4) Uani 1 1 d . . . . .
C28 C 0.9858(2) 0.47878(8) 0.75382(16) 0.0218(4) Uani 1 1 d . . . . .
C29 C 1.0925(2) 0.46806(8) 0.85418(16) 0.0203(4) Uani 1 1 d . . . . .
C30 C 1.1746(2) 0.51173(8) 0.91340(16) 0.0217(4) Uani 1 1 d . . . . .
H30 H 1.158830 0.548889 0.887746 0.026 Uiso 1 1 calc R U . . .
C31 C 1.2788(2) 0.50033(9) 1.00948(17) 0.0247(4) Uani 1 1 d . . . . .
H31 H 1.334980 0.529817 1.049376 0.030 Uiso 1 1 calc R U . . .
C32 C 1.3019(2) 0.44633(9) 1.04783(17) 0.0267(4) Uani 1 1 d . . . . .
H32 H 1.373315 0.438892 1.113884 0.032 Uiso 1 1 calc R U . . .
C33 C 1.2205(3) 0.40306(9) 0.98970(18) 0.0273(4) Uani 1 1 d . . . . .
H33 H 1.236322 0.366031 1.016122 0.033 Uiso 1 1 calc R U . . .
C34 C 1.1167(2) 0.41365(8) 0.89372(17) 0.0239(4) Uani 1 1 d . . . . .
H34 H 1.061335 0.383868 0.854280 0.029 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.8983(18) . ?
C2 C3 1.371(3) . ?
C2 C14 1.433(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.410(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.353(3) . ?
C5 C6 1.415(3) . ?
C5 F15 1.353(2) . ?
C6 C7 1.410(3) . ?
C6 C14 1.442(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.368(3) . ?
C8 C9 1.480(2) . ?
C8 C12 1.396(2) . ?
C9 N10 1.403(2) . ?
C9 O16 1.209(2) . ?
N10 C11 1.481(2) . ?
N10 S17 1.6703(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.504(3) . ?
C12 C13 1.386(3) . ?
C13 C14 1.440(3) . ?
C13 C27 1.427(2) . ?
S17 O18 1.4310(14) . ?
S17 O19 1.4308(14) . ?
S17 C20 1.755(2) . ?
C20 C21 1.393(3) . ?
C20 C25 1.400(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.396(3) . ?
C23 C24 1.402(3) . ?
C23 C26 1.503(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.382(3) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.202(3) . ?
C28 C29 1.432(3) . ?
C29 C30 1.404(3) . ?
C29 C34 1.399(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.386(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.384(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.388(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.379(3) . ?
C34 H34 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 Br1 114.86(14) . . ?
C3 C2 C14 122.45(17) . . ?
C14 C2 Br1 122.68(14) . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.15(18) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 121.2 . . ?
C5 C4 C3 117.62(18) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 C6 124.14(18) . . ?
C4 C5 F15 119.15(17) . . ?
F15 C5 C6 116.72(16) . . ?
C5 C6 C14 118.63(16) . . ?
C7 C6 C5 119.46(16) . . ?
C7 C6 C14 121.89(16) . . ?
C6 C7 H7 121.0 . . ?
C8 C7 C6 118.03(16) . . ?
C8 C7 H7 121.0 . . ?
C7 C8 C9 128.63(16) . . ?
C7 C8 C12 121.64(17) . . ?
C12 C8 C9 109.70(16) . . ?
N10 C9 C8 104.89(15) . . ?
O16 C9 C8 128.99(17) . . ?
O16 C9 N10 126.12(17) . . ?
C9 N10 C11 113.67(15) . . ?
C9 N10 S17 124.29(13) . . ?
C11 N10 S17 121.63(12) . . ?
N10 C11 H11A 111.5 . . ?
N10 C11 H11B 111.5 . . ?
N10 C11 C12 101.52(14) . . ?
H11A C11 H11B 109.3 . . ?
C12 C11 H11A 111.5 . . ?
C12 C11 H11B 111.5 . . ?
C8 C12 C11 110.17(16) . . ?
C13 C12 C8 122.66(17) . . ?
C13 C12 C11 127.15(16) . . ?
C12 C13 C14 117.88(16) . . ?
C12 C13 C27 115.46(17) . . ?
C27 C13 C14 126.63(17) . . ?
C2 C14 C6 115.91(16) . . ?
C2 C14 C13 126.20(16) . . ?
C13 C14 C6 117.89(16) . . ?
N10 S17 C20 105.22(9) . . ?
O18 S17 N10 108.51(8) . . ?
O18 S17 C20 108.28(9) . . ?
O19 S17 N10 103.67(8) . . ?
O19 S17 O18 120.48(9) . . ?
O19 S17 C20 109.60(9) . . ?
C21 C20 S17 119.84(15) . . ?
C21 C20 C25 121.34(19) . . ?
C25 C20 S17 118.80(15) . . ?
C20 C21 H21 120.7 . . ?
C22 C21 C20 118.57(18) . . ?
C22 C21 H21 120.7 . . ?
C21 C22 H22 119.3 . . ?
C21 C22 C23 121.45(18) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 C24 118.68(19) . . ?
C22 C23 C26 120.98(18) . . ?
C24 C23 C26 120.33(18) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 C23 120.99(18) . . ?
C25 C24 H24 119.5 . . ?
C20 C25 H25 120.5 . . ?
C24 C25 C20 118.95(18) . . ?
C24 C25 H25 120.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C13 167.6(2) . . ?
C27 C28 C29 176.7(2) . . ?
C30 C29 C28 120.61(18) . . ?
C34 C29 C28 120.07(17) . . ?
C34 C29 C30 119.32(17) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 C29 119.62(18) . . ?
C31 C30 H30 120.2 . . ?
C30 C31 H31 119.7 . . ?
C32 C31 C30 120.57(18) . . ?
C32 C31 H31 119.7 . . ?
C31 C32 H32 120.0 . . ?
C31 C32 C33 119.96(18) . . ?
C33 C32 H32 120.0 . . ?
C32 C33 H33 119.9 . . ?
C34 C33 C32 120.24(19) . . ?
C34 C33 H33 119.9 . . ?
C29 C34 H34 119.9 . . ?
C33 C34 C29 120.29(18) . . ?
C33 C34 H34 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C2 C3 C4 -177.54(15) . . . . ?
Br1 C2 C14 C6 176.27(12) . . . . ?
Br1 C2 C14 C13 -4.7(3) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
C3 C2 C14 C6 -2.6(3) . . . . ?
C3 C2 C14 C13 176.45(18) . . . . ?
C3 C4 C5 C6 -3.4(3) . . . . ?
C3 C4 C5 F15 177.12(16) . . . . ?
C4 C5 C6 C7 -176.51(18) . . . . ?
C4 C5 C6 C14 2.1(3) . . . . ?
C5 C6 C7 C8 178.17(16) . . . . ?
C5 C6 C14 C2 0.9(2) . . . . ?
C5 C6 C14 C13 -178.22(16) . . . . ?
C6 C7 C8 C9 -176.87(17) . . . . ?
C6 C7 C8 C12 0.9(3) . . . . ?
C7 C6 C14 C2 179.49(16) . . . . ?
C7 C6 C14 C13 0.3(3) . . . . ?
C7 C8 C9 N10 -179.73(17) . . . . ?
C7 C8 C9 O16 0.7(3) . . . . ?
C7 C8 C12 C11 179.75(16) . . . . ?
C7 C8 C12 C13 -1.4(3) . . . . ?
C8 C9 N10 C11 -1.7(2) . . . . ?
C8 C9 N10 S17 -174.41(12) . . . . ?
C8 C12 C13 C14 1.3(3) . . . . ?
C8 C12 C13 C27 -176.61(16) . . . . ?
C9 C8 C12 C11 -2.1(2) . . . . ?
C9 C8 C12 C13 176.71(16) . . . . ?
C9 N10 C11 C12 0.46(19) . . . . ?
C9 N10 S17 O18 47.74(17) . . . . ?
C9 N10 S17 O19 176.93(15) . . . . ?
C9 N10 S17 C20 -67.98(17) . . . . ?
N10 C11 C12 C8 1.04(19) . . . . ?
N10 C11 C12 C13 -177.72(17) . . . . ?
N10 S17 C20 C21 85.09(16) . . . . ?
N10 S17 C20 C25 -96.41(16) . . . . ?
C11 N10 S17 O18 -124.45(14) . . . . ?
C11 N10 S17 O19 4.74(16) . . . . ?
C11 N10 S17 C20 119.83(15) . . . . ?
C11 C12 C13 C14 179.96(16) . . . . ?
C11 C12 C13 C27 2.0(3) . . . . ?
C12 C8 C9 N10 2.3(2) . . . . ?
C12 C8 C9 O16 -177.25(19) . . . . ?
C12 C13 C14 C2 -179.84(17) . . . . ?
C12 C13 C14 C6 -0.8(2) . . . . ?
C12 C13 C27 C28 11.2(10) . . . . ?
C14 C2 C3 C4 1.4(3) . . . . ?
C14 C6 C7 C8 -0.4(3) . . . . ?
C14 C13 C27 C28 -166.5(8) . . . . ?
F15 C5 C6 C7 3.0(3) . . . . ?
F15 C5 C6 C14 -178.37(15) . . . . ?
O16 C9 N10 C11 177.91(18) . . . . ?
O16 C9 N10 S17 5.2(3) . . . . ?
S17 N10 C11 C12 173.42(12) . . . . ?
S17 C20 C21 C22 178.42(14) . . . . ?
S17 C20 C25 C24 -178.06(15) . . . . ?
O18 S17 C20 C21 -30.79(18) . . . . ?
O18 S17 C20 C25 147.72(15) . . . . ?
O19 S17 C20 C21 -164.00(15) . . . . ?
O19 S17 C20 C25 14.51(18) . . . . ?
C20 C21 C22 C23 -0.9(3) . . . . ?
C21 C20 C25 C24 0.4(3) . . . . ?
C21 C22 C23 C24 1.5(3) . . . . ?
C21 C22 C23 C26 -177.23(18) . . . . ?
C22 C23 C24 C25 -1.1(3) . . . . ?
C23 C24 C25 C20 0.2(3) . . . . ?
C25 C20 C21 C22 -0.1(3) . . . . ?
C26 C23 C24 C25 177.63(18) . . . . ?
C27 C13 C14 C2 -2.2(3) . . . . ?
C27 C13 C14 C6 176.90(17) . . . . ?
C28 C29 C30 C31 -179.24(17) . . . . ?
C28 C29 C34 C33 179.43(18) . . . . ?
C29 C30 C31 C32 -0.3(3) . . . . ?
C30 C29 C34 C33 -0.2(3) . . . . ?
C30 C31 C32 C33 0.2(3) . . . . ?
C31 C32 C33 C34 0.0(3) . . . . ?
C32 C33 C34 C29 0.0(3) . . . . ?
C34 C29 C30 C31 0.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_F161
_database_code_depnum_ccdc_archive 'CCDC 2161059'
loop_
_audit_author_name
_audit_author_address
'Lukasz Wojtas'
;university of south florida
United States of America
;
_audit_update_record             
;
2022-03-22 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;
_audit_creation_date             2022-03-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H20 N4 O3 S'
_chemical_formula_sum            'C27 H20 N4 O3 S'
_chemical_formula_weight         480.53
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.2159(2)
_cell_length_b                   24.1709(5)
_cell_length_c                   21.1041(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.4372(7)
_cell_angle_gamma                90
_cell_volume                     4607.73(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    296.00
_cell_measurement_theta_max      79.99
_cell_measurement_theta_min      4.27
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.755
_exptl_absorpt_coefficient_mu    1.565
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0956 before and 0.0665 after correction.
The Ratio of minimum to maximum transmission is 0.8857.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            99565
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.365
_diffrn_reflns_theta_min         2.812
_diffrn_ambient_temperature      296.00
_diffrn_detector                 'Bruker PHOTON II CMOS area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon-II CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec Imus'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8302
_reflns_number_total             10021
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     641
_refine_ls_number_reflns         10021
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0629P)²+1.0535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1242
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C63(H63A,H63B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C30(H30), C31(H31), C33(H33), C34(H34), C41(H41), C42(H42),
  C43(H43), C44(H44), C45(H45), C54(H54), C55(H55), C56(H56), C57(H57),
 C59(H59), C70(H70), C71(H71), C73(H73), C74(H74)
2.c Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C75(H75A,H75B,H75C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 -0.0477(2) 0.28415(8) 0.39622(10) 0.0646(5) Uani 1 1 d . . . . .
H1 H -0.016076 0.312803 0.425065 0.077 Uiso 1 1 calc R U . . .
C2 C -0.0307(3) 0.22962(10) 0.41715(13) 0.0822(7) Uani 1 1 d . . . . .
H2 H 0.010496 0.221864 0.460124 0.099 Uiso 1 1 calc R U . . .
C3 C -0.0749(3) 0.18681(9) 0.37404(16) 0.0913(8) Uani 1 1 d . . . . .
H3 H -0.064104 0.150304 0.388098 0.110 Uiso 1 1 calc R U . . .
C4 C -0.1349(3) 0.19832(9) 0.31039(15) 0.0853(7) Uani 1 1 d . . . . .
H4 H -0.162010 0.169500 0.281264 0.102 Uiso 1 1 calc R U . . .
C5 C -0.1549(2) 0.25222(8) 0.28959(11) 0.0676(5) Uani 1 1 d . . . . .
H5 H -0.197363 0.259577 0.246669 0.081 Uiso 1 1 calc R U . . .
C6 C -0.11177(18) 0.29610(7) 0.33248(9) 0.0535(4) Uani 1 1 d . . . . .
C7 C -0.13863(17) 0.35327(7) 0.30825(7) 0.0466(3) Uani 1 1 d . . . . .
N8 N -0.24663(16) 0.36342(6) 0.25681(7) 0.0539(3) Uani 1 1 d . . . . .
N9 N -0.23720(16) 0.41685(6) 0.24730(6) 0.0519(3) Uani 1 1 d . . . . .
H9 H -0.299(2) 0.4335(9) 0.2138(11) 0.070(6) Uiso 1 1 d . . . . .
N10 N -0.13255(15) 0.44363(6) 0.28763(6) 0.0489(3) Uani 1 1 d . . . . .
C11 C -0.06743(17) 0.40370(6) 0.32750(6) 0.0425(3) Uani 1 1 d . . . . .
C12 C 0.05914(17) 0.41696(6) 0.38071(7) 0.0418(3) Uani 1 1 d . . . . .
C13 C 0.20530(17) 0.42519(6) 0.36907(7) 0.0430(3) Uani 1 1 d . . . . .
C14 C 0.23820(19) 0.42323(7) 0.30626(8) 0.0509(4) Uani 1 1 d . . . . .
H14 H 0.163219 0.414928 0.271106 0.061 Uiso 1 1 calc R U . . .
C15 C 0.3781(2) 0.43330(8) 0.29638(9) 0.0617(4) Uani 1 1 d . . . . .
H15 H 0.396578 0.432145 0.254646 0.074 Uiso 1 1 calc R U . . .
C16 C 0.4940(2) 0.44535(9) 0.34847(10) 0.0650(5) Uani 1 1 d . . . . .
H16 H 0.588404 0.452620 0.341127 0.078 Uiso 1 1 calc R U . . .
C17 C 0.46817(19) 0.44637(8) 0.40966(9) 0.0576(4) Uani 1 1 d . . . . .
H17 H 0.546017 0.453617 0.444021 0.069 Uiso 1 1 calc R U . . .
C18 C 0.32529(18) 0.43664(6) 0.42200(7) 0.0465(3) Uani 1 1 d . . . . .
C19 C 0.29774(18) 0.43979(7) 0.48546(7) 0.0497(4) Uani 1 1 d . . . . .
H19 H 0.374705 0.446205 0.520454 0.060 Uiso 1 1 calc R U . . .
C20 C 0.15623(18) 0.43325(7) 0.49439(7) 0.0471(3) Uani 1 1 d . . . . .
C21 C 0.1013(2) 0.43628(7) 0.55522(7) 0.0532(4) Uani 1 1 d . . . . .
N22 N -0.05341(17) 0.42880(6) 0.53771(6) 0.0547(3) Uani 1 1 d . . . . .
C23 C -0.10394(19) 0.41854(8) 0.46776(7) 0.0521(4) Uani 1 1 d . . . . .
H23A H -0.174263 0.446450 0.448072 0.063 Uiso 1 1 calc R U . . .
H23B H -0.148941 0.382272 0.459860 0.063 Uiso 1 1 calc R U . . .
C24 C 0.03727(17) 0.42209(6) 0.44286(7) 0.0442(3) Uani 1 1 d . . . . .
O25 O 0.17102(16) 0.44412(7) 0.60922(6) 0.0738(4) Uani 1 1 d . . . . .
S26 S -0.16225(5) 0.41108(2) 0.58860(2) 0.05938(13) Uani 1 1 d . . . . .
O27 O -0.10702(19) 0.43814(6) 0.64809(6) 0.0755(4) Uani 1 1 d . . . . .
O28 O -0.30881(16) 0.42068(7) 0.55374(7) 0.0806(4) Uani 1 1 d . . . . .
C29 C -0.13539(19) 0.33950(8) 0.59804(8) 0.0536(4) Uani 1 1 d . . . . .
C30 C -0.0095(2) 0.32012(8) 0.63863(9) 0.0651(5) Uani 1 1 d . . . . .
H30 H 0.059928 0.344754 0.660853 0.078 Uiso 1 1 calc R U . . .
C31 C 0.0122(2) 0.26374(9) 0.64589(12) 0.0726(5) Uani 1 1 d . . . . .
H31 H 0.098156 0.250745 0.672502 0.087 Uiso 1 1 calc R U . . .
C32 C -0.0900(2) 0.22635(9) 0.61475(12) 0.0715(6) Uani 1 1 d . . . . .
C33 C -0.2143(3) 0.24698(11) 0.57369(13) 0.0850(7) Uani 1 1 d . . . . .
H33 H -0.283796 0.222299 0.551602 0.102 Uiso 1 1 calc R U . . .
C34 C -0.2383(2) 0.30298(11) 0.56454(11) 0.0737(6) Uani 1 1 d . . . . .
H34 H -0.322012 0.315932 0.536381 0.088 Uiso 1 1 calc R U . . .
C35 C -0.0664(4) 0.16516(10) 0.62590(18) 0.1068(10) Uani 1 1 d . . . . .
H35A H -0.041860 0.148465 0.588103 0.160 Uiso 1 1 calc R U . . .
H35B H -0.155301 0.148714 0.634497 0.160 Uiso 1 1 calc R U . . .
H35C H 0.013149 0.159305 0.662217 0.160 Uiso 1 1 calc R U . . .
C41 C 0.5120(2) 0.30482(7) 0.86253(9) 0.0578(4) Uani 1 1 d . . . . .
H41 H 0.587236 0.331056 0.870353 0.069 Uiso 1 1 calc R U . . .
C42 C 0.5408(3) 0.25102(9) 0.88378(12) 0.0755(6) Uani 1 1 d . . . . .
H42 H 0.634562 0.241414 0.906439 0.091 Uiso 1 1 calc R U . . .
C43 C 0.4312(3) 0.21193(9) 0.87141(16) 0.0929(8) Uani 1 1 d . . . . .
H43 H 0.450452 0.175715 0.885476 0.112 Uiso 1 1 calc R U . . .
C44 C 0.2935(3) 0.22628(10) 0.83836(18) 0.1028(10) Uani 1 1 d . . . . .
H44 H 0.219539 0.199576 0.829733 0.123 Uiso 1 1 calc R U . . .
C45 C 0.2629(2) 0.27979(9) 0.81767(13) 0.0750(6) Uani 1 1 d . . . . .
H45 H 0.168450 0.289017 0.795496 0.090 Uiso 1 1 calc R U . . .
C46 C 0.37222(17) 0.32003(6) 0.82973(8) 0.0468(3) Uani 1 1 d . . . . .
C47 C 0.33978(16) 0.37681(6) 0.80594(7) 0.0414(3) Uani 1 1 d . . . . .
N48 N 0.22806(15) 0.38788(6) 0.75636(6) 0.0498(3) Uani 1 1 d . . . . .
N49 N 0.23496(16) 0.44166(6) 0.74913(6) 0.0506(3) Uani 1 1 d . . . . .
H49 H 0.172(3) 0.4590(10) 0.7189(11) 0.076(7) Uiso 1 1 d . . . . .
N50 N 0.34223(15) 0.46782(6) 0.78917(6) 0.0474(3) Uani 1 1 d . . . . .
C51 C 0.41095(16) 0.42696(6) 0.82634(6) 0.0390(3) Uani 1 1 d . . . . .
C52 C 0.53484(16) 0.43653(6) 0.88156(6) 0.0380(3) Uani 1 1 d . . . . .
C53 C 0.68212(16) 0.44836(6) 0.87377(7) 0.0395(3) Uani 1 1 d . . . . .
C54 C 0.71920(18) 0.45441(7) 0.81210(7) 0.0476(3) Uani 1 1 d . . . . .
H54 H 0.645360 0.451239 0.775215 0.057 Uiso 1 1 calc R U . . .
C55 C 0.8615(2) 0.46482(8) 0.80582(9) 0.0564(4) Uani 1 1 d . . . . .
H55 H 0.883320 0.468742 0.764885 0.068 Uiso 1 1 calc R U . . .
C56 C 0.97479(19) 0.46963(8) 0.86086(9) 0.0589(4) Uani 1 1 d . . . . .
H56 H 1.070907 0.477525 0.856223 0.071 Uiso 1 1 calc R U . . .
C57 C 0.94467(18) 0.46281(7) 0.92086(8) 0.0516(4) Uani 1 1 d . . . . .
H57 H 1.021301 0.465108 0.956810 0.062 Uiso 1 1 calc R U . . .
C58 C 0.79857(16) 0.45225(6) 0.92971(7) 0.0422(3) Uani 1 1 d . . . . .
C59 C 0.76700(17) 0.44436(6) 0.99192(7) 0.0452(3) Uani 1 1 d . . . . .
H59 H 0.842072 0.446407 1.028486 0.054 Uiso 1 1 calc R U . . .
C60 C 0.62452(17) 0.43369(6) 0.99755(7) 0.0427(3) Uani 1 1 d . . . . .
C61 C 0.56380(19) 0.42207(7) 1.05589(7) 0.0492(4) Uani 1 1 d . . . . .
N62 N 0.41297(16) 0.41090(6) 1.03347(6) 0.0514(3) Uani 1 1 d . . . . .
C63 C 0.36778(17) 0.41411(7) 0.96265(7) 0.0480(3) Uani 1 1 d . . . . .
H63A H 0.292486 0.442183 0.949769 0.058 Uiso 1 1 calc R U . . .
H63B H 0.330928 0.378803 0.944349 0.058 Uiso 1 1 calc R U . . .
C64 C 0.50955(16) 0.42949(6) 0.94291(7) 0.0403(3) Uani 1 1 d . . . . .
O65 O 0.62624(16) 0.42098(6) 1.11191(5) 0.0672(4) Uani 1 1 d . . . . .
S66 S 0.29743(5) 0.38616(2) 1.07811(2) 0.05735(12) Uani 1 1 d . . . . .
O67 O 0.3129(2) 0.41811(6) 1.13519(7) 0.0803(4) Uani 1 1 d . . . . .
O68 O 0.15883(14) 0.38342(7) 1.03340(7) 0.0778(4) Uani 1 1 d . . . . .
C69 C 0.35816(18) 0.31879(7) 1.09915(8) 0.0507(4) Uani 1 1 d . . . . .
C70 C 0.4265(2) 0.30695(8) 1.16199(8) 0.0583(4) Uani 1 1 d . . . . .
H70 H 0.446804 0.335041 1.192571 0.070 Uiso 1 1 calc R U . . .
C71 C 0.4642(2) 0.25297(9) 1.17885(10) 0.0662(5) Uani 1 1 d . . . . .
H71 H 0.509648 0.245049 1.221275 0.079 Uiso 1 1 calc R U . . .
C72 C 0.4365(2) 0.21023(8) 1.13447(11) 0.0657(5) Uani 1 1 d . . . . .
C73 C 0.3706(3) 0.22328(9) 1.07151(12) 0.0766(6) Uani 1 1 d . . . . .
H73 H 0.352706 0.195250 1.040756 0.092 Uiso 1 1 calc R U . . .
C74 C 0.3310(2) 0.27669(9) 1.05324(10) 0.0691(5) Uani 1 1 d . . . . .
H74 H 0.286483 0.284607 1.010695 0.083 Uiso 1 1 calc R U . . .
C75 C 0.4772(3) 0.15148(10) 1.15436(15) 0.0950(8) Uani 1 1 d . . . . .
H75A H 0.394161 0.133586 1.166851 0.142 Uiso 1 1 calc R U . . .
H75B H 0.559628 0.151497 1.190192 0.142 Uiso 1 1 calc R U . . .
H75C H 0.503594 0.131926 1.118704 0.142 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
C1 H1 0.9300 . ?
C1 C2 1.389(3) . ?
C1 C6 1.388(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.400(3) . ?
C6 C7 1.477(2) . ?
C7 N8 1.3420(19) . ?
C7 C11 1.406(2) . ?
N8 N9 1.313(2) . ?
N9 H9 0.91(2) . ?
N9 N10 1.3221(18) . ?
N10 C11 1.3414(19) . ?
C11 C12 1.4848(19) . ?
C12 C13 1.430(2) . ?
C12 C24 1.372(2) . ?
C13 C14 1.418(2) . ?
C13 C18 1.434(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.368(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.403(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.359(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.412(2) . ?
C18 C19 1.414(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.363(2) . ?
C20 C21 1.472(2) . ?
C20 C24 1.409(2) . ?
C21 N22 1.412(2) . ?
C21 O25 1.2070(19) . ?
N22 C23 1.4782(19) . ?
N22 S26 1.6644(15) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.499(2) . ?
S26 O27 1.4176(14) . ?
S26 O28 1.4232(15) . ?
S26 C29 1.753(2) . ?
C29 C30 1.380(3) . ?
C29 C34 1.383(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.382(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.375(3) . ?
C32 C33 1.385(4) . ?
C32 C35 1.507(3) . ?
C33 H33 0.9300 . ?
C33 C34 1.379(4) . ?
C34 H34 0.9300 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C41 H41 0.9300 . ?
C41 C42 1.384(3) . ?
C41 C46 1.386(2) . ?
C42 H42 0.9300 . ?
C42 C43 1.370(3) . ?
C43 H43 0.9300 . ?
C43 C44 1.366(4) . ?
C44 H44 0.9300 . ?
C44 C45 1.376(3) . ?
C45 H45 0.9300 . ?
C45 C46 1.387(2) . ?
C46 C47 1.471(2) . ?
C47 N48 1.3414(18) . ?
C47 C51 1.404(2) . ?
N48 N49 1.312(2) . ?
N49 H49 0.88(2) . ?
N49 N50 1.3266(18) . ?
N50 C51 1.3398(18) . ?
C51 C52 1.4790(18) . ?
C52 C53 1.428(2) . ?
C52 C64 1.3708(19) . ?
C53 C54 1.417(2) . ?
C53 C58 1.4325(19) . ?
C54 H54 0.9300 . ?
C54 C55 1.367(2) . ?
C55 H55 0.9300 . ?
C55 C56 1.404(3) . ?
C56 H56 0.9300 . ?
C56 C57 1.359(3) . ?
C57 H57 0.9300 . ?
C57 C58 1.419(2) . ?
C58 C59 1.413(2) . ?
C59 H59 0.9300 . ?
C59 C60 1.366(2) . ?
C60 C61 1.477(2) . ?
C60 C64 1.4064(18) . ?
C61 N62 1.403(2) . ?
C61 O65 1.2083(18) . ?
N62 C63 1.4719(18) . ?
N62 S66 1.6663(14) . ?
C63 H63A 0.9700 . ?
C63 H63B 0.9700 . ?
C63 C64 1.495(2) . ?
S66 O67 1.4141(15) . ?
S66 O68 1.4312(15) . ?
S66 C69 1.7504(18) . ?
C69 C70 1.380(2) . ?
C69 C74 1.393(3) . ?
C70 H70 0.9300 . ?
C70 C71 1.379(3) . ?
C71 H71 0.9300 . ?
C71 C72 1.384(3) . ?
C72 C73 1.383(3) . ?
C72 C75 1.507(3) . ?
C73 H73 0.9300 . ?
C73 C74 1.376(3) . ?
C74 H74 0.9300 . ?
C75 H75A 0.9600 . ?
C75 H75B 0.9600 . ?
C75 H75C 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
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.4(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.73(17) . . ?
C1 C6 C7 122.69(16) . . ?
C5 C6 C7 118.57(16) . . ?
N8 C7 C6 119.84(14) . . ?
N8 C7 C11 107.71(13) . . ?
C11 C7 C6 132.42(14) . . ?
N9 N8 C7 104.04(13) . . ?
N8 N9 H9 120.4(14) . . ?
N8 N9 N10 116.44(13) . . ?
N10 N9 H9 123.1(14) . . ?
N9 N10 C11 103.31(13) . . ?
C7 C11 C12 131.10(13) . . ?
N10 C11 C7 108.51(12) . . ?
N10 C11 C12 120.39(13) . . ?
C13 C12 C11 121.71(13) . . ?
C24 C12 C11 120.02(14) . . ?
C24 C12 C13 118.27(13) . . ?
C12 C13 C18 120.00(14) . . ?
C14 C13 C12 122.62(13) . . ?
C14 C13 C18 117.37(15) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.28(15) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.77(17) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.90(18) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.19(16) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C13 119.45(15) . . ?
C17 C18 C19 121.01(14) . . ?
C19 C18 C13 119.51(15) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 C18 118.76(13) . . ?
C20 C19 H19 120.6 . . ?
C19 C20 C21 128.20(14) . . ?
C19 C20 C24 122.33(14) . . ?
C24 C20 C21 109.46(14) . . ?
N22 C21 C20 105.62(13) . . ?
O25 C21 C20 128.36(17) . . ?
O25 C21 N22 126.01(17) . . ?
C21 N22 C23 112.63(14) . . ?
C21 N22 S26 124.80(11) . . ?
C23 N22 S26 119.37(12) . . ?
N22 C23 H23A 111.3 . . ?
N22 C23 H23B 111.3 . . ?
N22 C23 C24 102.53(13) . . ?
H23A C23 H23B 109.2 . . ?
C24 C23 H23A 111.3 . . ?
C24 C23 H23B 111.3 . . ?
C12 C24 C20 121.07(15) . . ?
C12 C24 C23 129.22(13) . . ?
C20 C24 C23 109.70(13) . . ?
N22 S26 C29 103.75(8) . . ?
O27 S26 N22 107.23(9) . . ?
O27 S26 O28 121.32(10) . . ?
O27 S26 C29 109.68(8) . . ?
O28 S26 N22 104.84(8) . . ?
O28 S26 C29 108.53(10) . . ?
C30 C29 S26 119.19(14) . . ?
C30 C29 C34 120.5(2) . . ?
C34 C29 S26 120.32(16) . . ?
C29 C30 H30 120.4 . . ?
C29 C30 C31 119.28(18) . . ?
C31 C30 H30 120.4 . . ?
C30 C31 H31 119.2 . . ?
C32 C31 C30 121.7(2) . . ?
C32 C31 H31 119.2 . . ?
C31 C32 C33 117.8(2) . . ?
C31 C32 C35 120.4(2) . . ?
C33 C32 C35 121.8(2) . . ?
C32 C33 H33 119.0 . . ?
C34 C33 C32 122.06(19) . . ?
C34 C33 H33 119.0 . . ?
C29 C34 H34 120.6 . . ?
C33 C34 C29 118.7(2) . . ?
C33 C34 H34 120.6 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C42 C41 H41 119.6 . . ?
C42 C41 C46 120.73(18) . . ?
C46 C41 H41 119.6 . . ?
C41 C42 H42 120.0 . . ?
C43 C42 C41 119.9(2) . . ?
C43 C42 H42 120.0 . . ?
C42 C43 H43 120.1 . . ?
C44 C43 C42 119.8(2) . . ?
C44 C43 H43 120.1 . . ?
C43 C44 H44 119.6 . . ?
C43 C44 C45 120.8(2) . . ?
C45 C44 H44 119.6 . . ?
C44 C45 H45 119.8 . . ?
C44 C45 C46 120.3(2) . . ?
C46 C45 H45 119.8 . . ?
C41 C46 C45 118.36(17) . . ?
C41 C46 C47 121.58(14) . . ?
C45 C46 C47 120.03(15) . . ?
N48 C47 C46 121.65(13) . . ?
N48 C47 C51 107.85(13) . . ?
C51 C47 C46 130.49(13) . . ?
N49 N48 C47 103.95(12) . . ?
N48 N49 H49 121.0(16) . . ?
N48 N49 N50 116.44(12) . . ?
N50 N49 H49 122.6(16) . . ?
N49 N50 C51 103.16(13) . . ?
C47 C51 C52 128.11(13) . . ?
N50 C51 C47 108.60(12) . . ?
N50 C51 C52 123.19(13) . . ?
C53 C52 C51 122.92(12) . . ?
C64 C52 C51 118.39(13) . . ?
C64 C52 C53 118.49(12) . . ?
C52 C53 C58 119.48(13) . . ?
C54 C53 C52 122.28(13) . . ?
C54 C53 C58 118.19(14) . . ?
C53 C54 H54 119.4 . . ?
C55 C54 C53 121.24(15) . . ?
C55 C54 H54 119.4 . . ?
C54 C55 H55 119.8 . . ?
C54 C55 C56 120.35(16) . . ?
C56 C55 H55 119.8 . . ?
C55 C56 H56 119.8 . . ?
C57 C56 C55 120.31(16) . . ?
C57 C56 H56 119.8 . . ?
C56 C57 H57 119.4 . . ?
C56 C57 C58 121.27(15) . . ?
C58 C57 H57 119.4 . . ?
C57 C58 C53 118.61(14) . . ?
C59 C58 C53 119.89(14) . . ?
C59 C58 C57 121.49(13) . . ?
C58 C59 H59 120.5 . . ?
C60 C59 C58 119.00(13) . . ?
C60 C59 H59 120.5 . . ?
C59 C60 C61 129.64(13) . . ?
C59 C60 C64 121.54(14) . . ?
C64 C60 C61 108.75(13) . . ?
N62 C61 C60 105.63(12) . . ?
O65 C61 C60 129.37(16) . . ?
O65 C61 N62 125.00(16) . . ?
C61 N62 C63 113.21(13) . . ?
C61 N62 S66 125.45(11) . . ?
C63 N62 S66 120.61(11) . . ?
N62 C63 H63A 111.4 . . ?
N62 C63 H63B 111.4 . . ?
N62 C63 C64 102.07(12) . . ?
H63A C63 H63B 109.2 . . ?
C64 C63 H63A 111.4 . . ?
C64 C63 H63B 111.4 . . ?
C52 C64 C60 121.59(14) . . ?
C52 C64 C63 128.00(12) . . ?
C60 C64 C63 110.33(12) . . ?
N62 S66 C69 105.62(8) . . ?
O67 S66 N62 108.53(9) . . ?
O67 S66 O68 120.87(10) . . ?
O67 S66 C69 108.59(8) . . ?
O68 S66 N62 103.33(7) . . ?
O68 S66 C69 108.83(9) . . ?
C70 C69 S66 119.90(14) . . ?
C70 C69 C74 120.10(18) . . ?
C74 C69 S66 119.92(14) . . ?
C69 C70 H70 120.4 . . ?
C71 C70 C69 119.20(18) . . ?
C71 C70 H70 120.4 . . ?
C70 C71 H71 119.1 . . ?
C70 C71 C72 121.90(19) . . ?
C72 C71 H71 119.1 . . ?
C71 C72 C75 120.8(2) . . ?
C73 C72 C71 117.84(19) . . ?
C73 C72 C75 121.3(2) . . ?
C72 C73 H73 119.2 . . ?
C74 C73 C72 121.64(19) . . ?
C74 C73 H73 119.2 . . ?
C69 C74 H74 120.4 . . ?
C73 C74 C69 119.30(19) . . ?
C73 C74 H74 120.4 . . ?
C72 C75 H75A 109.5 . . ?
C72 C75 H75B 109.5 . . ?
C72 C75 H75C 109.5 . . ?
H75A C75 H75B 109.5 . . ?
H75A C75 H75C 109.5 . . ?
H75B C75 H75C 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 C2 C3 C4 0.4(4) . . . . ?
C1 C6 C7 N8 -154.33(18) . . . . ?
C1 C6 C7 C11 28.0(3) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C2 C1 C6 C7 177.27(19) . . . . ?
C2 C3 C4 C5 -1.7(4) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4 C5 C6 C7 -178.62(19) . . . . ?
C5 C6 C7 N8 24.6(3) . . . . ?
C5 C6 C7 C11 -153.01(19) . . . . ?
C6 C1 C2 C3 1.3(3) . . . . ?
C6 C7 N8 N9 -178.13(15) . . . . ?
C6 C7 C11 N10 177.72(17) . . . . ?
C6 C7 C11 C12 -1.6(3) . . . . ?
C7 N8 N9 N10 0.1(2) . . . . ?
C7 C11 C12 C13 101.4(2) . . . . ?
C7 C11 C12 C24 -79.2(2) . . . . ?
N8 C7 C11 N10 -0.14(19) . . . . ?
N8 C7 C11 C12 -179.49(16) . . . . ?
N8 N9 N10 C11 -0.15(19) . . . . ?
N9 N10 C11 C7 0.16(18) . . . . ?
N9 N10 C11 C12 179.60(14) . . . . ?
N10 C11 C12 C13 -77.9(2) . . . . ?
N10 C11 C12 C24 101.54(18) . . . . ?
C11 C7 N8 N9 0.05(18) . . . . ?
C11 C12 C13 C14 2.3(2) . . . . ?
C11 C12 C13 C18 -178.52(13) . . . . ?
C11 C12 C24 C20 178.37(14) . . . . ?
C11 C12 C24 C23 -2.9(2) . . . . ?
C12 C13 C14 C15 177.55(16) . . . . ?
C12 C13 C18 C17 -178.07(15) . . . . ?
C12 C13 C18 C19 -0.1(2) . . . . ?
C13 C12 C24 C20 -2.2(2) . . . . ?
C13 C12 C24 C23 176.55(15) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C13 C18 C19 C20 -1.7(2) . . . . ?
C14 C13 C18 C17 1.2(2) . . . . ?
C14 C13 C18 C19 179.14(14) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C15 C16 C17 C18 -1.4(3) . . . . ?
C16 C17 C18 C13 0.3(3) . . . . ?
C16 C17 C18 C19 -177.61(18) . . . . ?
C17 C18 C19 C20 176.20(16) . . . . ?
C18 C13 C14 C15 -1.7(2) . . . . ?
C18 C19 C20 C21 -178.27(16) . . . . ?
C18 C19 C20 C24 1.6(2) . . . . ?
C19 C20 C21 N22 177.68(17) . . . . ?
C19 C20 C21 O25 -1.5(3) . . . . ?
C19 C20 C24 C12 0.4(2) . . . . ?
C19 C20 C24 C23 -178.61(15) . . . . ?
C20 C21 N22 C23 2.37(19) . . . . ?
C20 C21 N22 S26 161.86(12) . . . . ?
C21 C20 C24 C12 -179.70(14) . . . . ?
C21 C20 C24 C23 1.32(18) . . . . ?
C21 N22 C23 C24 -1.58(19) . . . . ?
C21 N22 S26 O27 36.98(17) . . . . ?
C21 N22 S26 O28 167.16(15) . . . . ?
C21 N22 S26 C29 -79.06(16) . . . . ?
N22 C23 C24 C12 -178.77(15) . . . . ?
N22 C23 C24 C20 0.10(18) . . . . ?
N22 S26 C29 C30 78.57(16) . . . . ?
N22 S26 C29 C34 -100.60(16) . . . . ?
C23 N22 S26 O27 -164.80(13) . . . . ?
C23 N22 S26 O28 -34.62(16) . . . . ?
C23 N22 S26 C29 79.16(14) . . . . ?
C24 C12 C13 C14 -177.15(14) . . . . ?
C24 C12 C13 C18 2.1(2) . . . . ?
C24 C20 C21 N22 -2.24(18) . . . . ?
C24 C20 C21 O25 178.56(19) . . . . ?
O25 C21 N22 C23 -178.41(18) . . . . ?
O25 C21 N22 S26 -18.9(3) . . . . ?
S26 N22 C23 C24 -162.30(11) . . . . ?
S26 C29 C30 C31 -179.68(17) . . . . ?
S26 C29 C34 C33 -179.30(17) . . . . ?
O27 S26 C29 C30 -35.72(18) . . . . ?
O27 S26 C29 C34 145.10(16) . . . . ?
O28 S26 C29 C30 -170.33(15) . . . . ?
O28 S26 C29 C34 10.50(18) . . . . ?
C29 C30 C31 C32 -1.4(3) . . . . ?
C30 C29 C34 C33 1.5(3) . . . . ?
C30 C31 C32 C33 2.2(3) . . . . ?
C30 C31 C32 C35 -177.3(2) . . . . ?
C31 C32 C33 C34 -1.2(3) . . . . ?
C32 C33 C34 C29 -0.7(3) . . . . ?
C34 C29 C30 C31 -0.5(3) . . . . ?
C35 C32 C33 C34 178.4(2) . . . . ?
C41 C42 C43 C44 -0.3(4) . . . . ?
C41 C46 C47 N48 155.81(16) . . . . ?
C41 C46 C47 C51 -23.2(3) . . . . ?
C42 C41 C46 C45 -1.2(3) . . . . ?
C42 C41 C46 C47 -179.13(18) . . . . ?
C42 C43 C44 C45 -0.5(5) . . . . ?
C43 C44 C45 C46 0.5(5) . . . . ?
C44 C45 C46 C41 0.4(4) . . . . ?
C44 C45 C46 C47 178.4(2) . . . . ?
C45 C46 C47 N48 -22.1(2) . . . . ?
C45 C46 C47 C51 158.94(19) . . . . ?
C46 C41 C42 C43 1.2(4) . . . . ?
C46 C47 N48 N49 -179.46(14) . . . . ?
C46 C47 C51 N50 179.08(15) . . . . ?
C46 C47 C51 C52 -4.5(3) . . . . ?
C47 N48 N49 N50 0.49(19) . . . . ?
C47 C51 C52 C53 107.52(18) . . . . ?
C47 C51 C52 C64 -67.3(2) . . . . ?
N48 C47 C51 N50 -0.01(17) . . . . ?
N48 C47 C51 C52 176.36(14) . . . . ?
N48 N49 N50 C51 -0.49(18) . . . . ?
N49 N50 C51 C47 0.28(16) . . . . ?
N49 N50 C51 C52 -176.31(14) . . . . ?
N50 C51 C52 C53 -76.59(19) . . . . ?
N50 C51 C52 C64 108.61(17) . . . . ?
C51 C47 N48 N49 -0.27(16) . . . . ?
C51 C52 C53 C54 3.1(2) . . . . ?
C51 C52 C53 C58 -174.47(13) . . . . ?
C51 C52 C64 C60 175.05(13) . . . . ?
C51 C52 C64 C63 -1.6(2) . . . . ?
C52 C53 C54 C55 -178.89(15) . . . . ?
C52 C53 C58 C57 178.61(13) . . . . ?
C52 C53 C58 C59 0.0(2) . . . . ?
C53 C52 C64 C60 0.0(2) . . . . ?
C53 C52 C64 C63 -176.58(14) . . . . ?
C53 C54 C55 C56 0.2(3) . . . . ?
C53 C58 C59 C60 -0.7(2) . . . . ?
C54 C53 C58 C57 1.0(2) . . . . ?
C54 C53 C58 C59 -177.61(14) . . . . ?
C54 C55 C56 C57 1.4(3) . . . . ?
C55 C56 C57 C58 -1.8(3) . . . . ?
C56 C57 C58 C53 0.5(2) . . . . ?
C56 C57 C58 C59 179.11(16) . . . . ?
C57 C58 C59 C60 -179.26(15) . . . . ?
C58 C53 C54 C55 -1.3(2) . . . . ?
C58 C59 C60 C61 177.60(15) . . . . ?
C58 C59 C60 C64 1.1(2) . . . . ?
C59 C60 C61 N62 -176.53(16) . . . . ?
C59 C60 C61 O65 2.4(3) . . . . ?
C59 C60 C64 C52 -0.7(2) . . . . ?
C59 C60 C64 C63 176.41(14) . . . . ?
C60 C61 N62 C63 0.22(18) . . . . ?
C60 C61 N62 S66 170.41(12) . . . . ?
C61 C60 C64 C52 -177.92(13) . . . . ?
C61 C60 C64 C63 -0.77(18) . . . . ?
C61 N62 C63 C64 -0.65(18) . . . . ?
C61 N62 S66 O67 49.42(17) . . . . ?
C61 N62 S66 O68 178.88(15) . . . . ?
C61 N62 S66 C69 -66.87(16) . . . . ?
N62 C63 C64 C52 177.77(15) . . . . ?
N62 C63 C64 C60 0.85(17) . . . . ?
N62 S66 C69 C70 108.32(15) . . . . ?
N62 S66 C69 C74 -74.83(16) . . . . ?
C63 N62 S66 O67 -141.07(14) . . . . ?
C63 N62 S66 O68 -11.61(16) . . . . ?
C63 N62 S66 C69 102.64(14) . . . . ?
C64 C52 C53 C54 177.84(14) . . . . ?
C64 C52 C53 C58 0.3(2) . . . . ?
C64 C60 C61 N62 0.34(17) . . . . ?
C64 C60 C61 O65 179.24(17) . . . . ?
O65 C61 N62 C63 -178.74(17) . . . . ?
O65 C61 N62 S66 -8.6(3) . . . . ?
S66 N62 C63 C64 -171.36(11) . . . . ?
S66 C69 C70 C71 175.44(15) . . . . ?
S66 C69 C74 C73 -175.76(17) . . . . ?
O67 S66 C69 C70 -7.93(18) . . . . ?
O67 S66 C69 C74 168.93(16) . . . . ?
O68 S66 C69 C70 -141.30(15) . . . . ?
O68 S66 C69 C74 35.56(18) . . . . ?
C69 C70 C71 C72 0.4(3) . . . . ?
C70 C69 C74 C73 1.1(3) . . . . ?
C70 C71 C72 C73 0.8(3) . . . . ?
C70 C71 C72 C75 -179.2(2) . . . . ?
C71 C72 C73 C74 -1.2(3) . . . . ?
C72 C73 C74 C69 0.2(3) . . . . ?
C74 C69 C70 C71 -1.4(3) . . . . ?
C75 C72 C73 C74 178.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
