#------------------------------------------------------------------------------
#$Date: 2024-11-05 03:32:48 +0200 (Tue, 05 Nov 2024) $
#$Revision: 295769 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160205.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7160205
loop_
_publ_author_name
'Liu, Pan'
'Geng, Yang'
'Zou, Dapeng'
'Wu, Yangjie'
'Wu, Yusheng'
_publ_section_title
;
Silver-mediated radical cascade trifluoromethylthiolation/cyclization of
benzimidazole derivatives with AgSCF3.
;
_journal_name_full 'Organic & biomolecular chemistry'
_journal_paper_doi 10.1039/d4ob01582g
_journal_year 2024
_chemical_formula_moiety 'C13 H13 F3 N2 S'
_chemical_formula_sum 'C13 H13 F3 N2 S'
_chemical_formula_weight 286.31
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_Hall '-P 1'
_space_group_name_H-M_alt 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_audit_creation_date 2024-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-06-04 deposited with the CCDC. 2024-10-28 downloaded from the CCDC.
;
_cell_angle_alpha 67.284(6)
_cell_angle_beta 85.636(5)
_cell_angle_gamma 87.696(5)
_cell_formula_units_Z 4
_cell_length_a 6.5464(4)
_cell_length_b 13.7584(8)
_cell_length_c 16.2007(10)
_cell_measurement_reflns_used 2645
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 70.7140
_cell_measurement_theta_min 3.5960
_cell_volume 1341.98(15)
_computing_cell_refinement 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction 'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature 293(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):
# Type Start End Width t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w -56.00 37.00 1.00 1.00 -- -33.50 37.00 -60.00 93
2 \w -104.00 -11.00 1.00 1.00 -- -33.50 -37.00 126.00 93
3 \w -52.00 35.00 1.00 1.00 -- -33.50 57.00 60.00 87
4 \w 18.00 105.00 1.00 1.00 -- 36.47 57.00 0.00 87
5 \w -18.00 65.00 1.00 1.00 -- 36.47 -77.00 0.00 83
6 \w -30.00 -4.00 1.00 1.00 -- 36.47 -57.00-150.00 26
7 \w -12.00 15.00 1.00 1.00 -- 36.47 -37.00-150.00 27
8 \w 67.00 110.00 1.00 1.00 -- 36.47 178.00-180.00 43
9 \w 38.00 64.00 1.00 1.00 -- 36.47 -99.00 30.00 26
10 \w -5.00 21.00 1.00 1.00 -- 36.47 -77.00-150.00 26
11 \w 34.00 59.00 1.00 1.00 -- 36.47 -37.00-150.00 25
12 \w 37.00 73.00 1.00 1.00 -- 36.47 -99.00-120.00 36
13 \w 6.00 34.00 1.00 1.00 -- 36.47 -99.00 30.00 28
14 \w 7.00 74.00 1.00 1.00 -- 36.47 -99.00 120.00 67
15 \w 6.00 55.00 1.00 1.00 -- 36.47 -57.00-150.00 49
16 \w 55.00 98.00 1.00 7.50 -- 108.00 -94.00-180.00 43
17 \w 37.00 92.00 1.00 7.50 -- 108.00 -30.00 -30.00 55
18 \w 149.00 176.00 1.00 7.50 -- 108.00 61.00-150.00 27
19 \w 38.00 128.00 1.00 7.50 -- 108.00 -45.00-120.00 90
20 \w 52.00 123.00 1.00 7.50 -- 108.00 -61.00 -60.00 71
21 \w 92.00 124.00 1.00 7.50 -- 108.00 61.00-150.00 32
22 \w 74.00 100.00 1.00 7.50 -- 108.00-111.00 90.00 26
23 \w 41.00 108.00 1.00 7.50 -- 108.00-111.00 120.00 67
24 \w 62.00 117.00 1.00 7.50 -- 108.00 178.00 -60.00 55
25 \w 113.00 169.00 1.00 7.50 -- 108.00 77.00 30.00 56
26 \w 48.00 74.00 1.00 7.50 -- 108.00-111.00 -30.00 26
27 \w 42.00 119.00 1.00 7.50 -- 108.00 -45.00 60.00 77
28 \w 66.00 104.00 1.00 7.50 -- 108.00 -94.00 -30.00 38
29 \w 45.00 71.00 1.00 7.50 -- 108.00 -61.00 60.00 26
30 \w 42.00 109.00 1.00 7.50 -- 108.00-111.00 -90.00 67
31 \w 41.00 173.00 1.00 7.50 -- 108.00 0.00 0.00 132
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Eos, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 0.1768513000
_diffrn_orient_matrix_UB_12 -0.0421558000
_diffrn_orient_matrix_UB_13 -0.0457434000
_diffrn_orient_matrix_UB_21 -0.1523465000
_diffrn_orient_matrix_UB_22 -0.0677461000
_diffrn_orient_matrix_UB_23 -0.0219021000
_diffrn_orient_matrix_UB_31 -0.0350024000
_diffrn_orient_matrix_UB_32 0.0914902000
_diffrn_orient_matrix_UB_33 -0.0900064000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_reflns_av_R_equivalents 0.0297
_diffrn_reflns_av_unetI/netI 0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_number 9426
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full 67.078
_diffrn_reflns_theta_max 67.078
_diffrn_reflns_theta_min 3.483
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu 2.381
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.49754
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.417
_exptl_crystal_description block
_exptl_crystal_F_000 592
_exptl_crystal_size_max 0.17
_exptl_crystal_size_mid 0.11
_exptl_crystal_size_min 0.04
_refine_diff_density_max 0.679
_refine_diff_density_min -0.433
_refine_diff_density_rms 0.073
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.197
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 402
_refine_ls_number_reflns 4763
_refine_ls_number_restraints 113
_refine_ls_restrained_S_all 1.283
_refine_ls_R_factor_all 0.1330
_refine_ls_R_factor_gt 0.1078
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2300P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.3296
_refine_ls_wR_factor_ref 0.3717
_reflns_Friedel_coverage 0.000
_reflns_number_gt 3273
_reflns_number_total 4763
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file d4ob01582g2.cif
_cod_data_source_block 202405199b_auto
_cod_database_code 7160205
_shelx_shelxl_version_number 2014/7
_chemical_oxdiff_formula C20H2N1O4S1F2
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max 0.911
_shelx_estimated_absorpt_t_min 0.688
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 66.97
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
C10'-C9'
1.64 with sigma of 0.02
C10'-C11'
1.64 with sigma of 0.02
C10B-C11'
1.54 with sigma of 0.02
C9'A-C10B
1.54 with sigma of 0.02
S1'A-C13B
1.78 with sigma of 0.02
F2'A-S1'A
2.5 with sigma of 0.02
C11A-C10A
1.54 with sigma of 0.02
S1A-C12A
1.78 with sigma of 0.02
C8A-C12A
1.54 with sigma of 0.02
C10-C9
1.54 with sigma of 0.02
C9A-C8A
1.54 with sigma of 0.02
C10A-C9A
1.54 with sigma of 0.02
S1A-F2A
2.2 with sigma of 0.02
S1A-F3A
2.3 with sigma of 0.02
C11A-N2
1.45 with sigma of 0.02
S1'A-F3'A
2.3 with sigma of 0.02
S1'A-F1'A
2.3 with sigma of 0.02
F3A-F2A
1.8 with sigma of 0.02
F3A-F1A
1.8 with sigma of 0.02
C13B-F1'A = C13B-F3'A = C13B-F2'A
1.35 with sigma of 0.02
C13A-F3A
1.35 with sigma of 0.02
C8'-C12'
1.68 with sigma of 0.02
C8'A-C12B
1.54 with sigma of 0.02
C9'-C8'
1.78 with sigma of 0.02
C9'A-C8'A
1.54 with sigma of 0.02
S1'-C12'
1.78 with sigma of 0.02
C7'-C8'A
1.54 with sigma of 0.02
F3'-F1' \\sim F3'-F2' \\sim F1'-F2'
with sigma of 0.04
C13'-F3' \\sim C13'-F1' \\sim C13'-F2'
with sigma of 0.02
F1'A-F3'A \\sim F1'A-F2'A \\sim F3'A-F2'A
with sigma of 0.04
C13B-F1'A \\sim C13B-F3'A \\sim C13B-F2'A
with sigma of 0.02
F3A-F2A \\sim F3A-F1A \\sim F2A-F1A
with sigma of 0.04
C13A-F3A \\sim C13A-F2A \\sim C13A-F1A
with sigma of 0.02
F1-F2 \\sim F1-F3 \\sim F2-F3
with sigma of 0.04
C13-F1 \\sim C13-F2 \\sim C13-F3
with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C10B) \\sim Ueq, Uanis(C10') \\sim Ueq, Uanis(C9'A) \\sim Ueq, Uanis(C9')
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F2'A) \\sim Ueq, Uanis(F2') \\sim Ueq, Uanis(F3') \\sim Ueq, Uanis(F3'A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C8') \\sim Ueq, Uanis(C8'A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C10') = Uanis(C10B)
Uanis(C9') = Uanis(C9'A)
Uanis(C8') = Uanis(C8'A)
Uanis(C12') = Uanis(C12B)
Uanis(S1') = Uanis(S1'A)
Uanis(C13') = Uanis(C13B)
Uanis(F1') = Uanis(F1'A)
Uanis(F3') = Uanis(F3'A)
Uanis(F2') = Uanis(F2'A)
Uanis(C11) = Uanis(C11A)
Uanis(C10) = Uanis(C10A)
Uanis(C9) = Uanis(C9A)
Uanis(C8) = Uanis(C8A)
Uanis(C12) = Uanis(C12A)
Uanis(S1) = Uanis(S1A)
Uanis(C13) = Uanis(C13A)
Uanis(F3) = Uanis(F3A)
Uanis(F2) = Uanis(F2A)
Uanis(F1) = Uanis(F1A)
4. Others
Sof(S1'A)=Sof(F1'A)=Sof(F2'A)=Sof(F3'A)=Sof(C8'A)=Sof(H8'A)=Sof(C9'A)=
Sof(H9'C)=Sof(H9'D)=Sof(C10B)=Sof(H10G)=Sof(H10H)=Sof(H11G)=Sof(H11H)=
Sof(C12B)=Sof(H12G)=Sof(H12H)=Sof(C13B)=1-FVAR(1)
Sof(S1')=Sof(F1')=Sof(F2')=Sof(F3')=Sof(C8')=Sof(H8')=Sof(C9')=Sof(H9'A)=
Sof(H9'B)=Sof(C10')=Sof(H10E)=Sof(H10F)=Sof(H11E)=Sof(H11F)=Sof(C12')=
Sof(H12E)=Sof(H12F)=Sof(C13')=FVAR(1)
Sof(S1A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9AA)=
Sof(H9AB)=Sof(C10A)=Sof(H10C)=Sof(H10D)=Sof(C11A)=Sof(H11C)=Sof(H11D)=
Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=1-FVAR(2)
Sof(S1)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9A)=Sof(H9B)=
Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=
Sof(H12B)=Sof(C13)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
C8(H8), C8A(H8A), C8'(H8'), C8'A(H8'A)
5.b Secondary CH2 refined with riding coordinates:
C9(H9A,H9B), C9A(H9AA,H9AB), C10(H10A,H10B), C10A(H10C,H10D), C11(H11A,H11B),
C11A(H11C,H11D), C12(H12A,H12B), C12A(H12C,H12D), C9'(H9'A,H9'B), C9'A(H9'C,
H9'D), C10'(H10E,H10F), C10B(H10G,H10H), C11'(H11E,H11F), C11'(H11G,H11H),
C12'(H12E,H12F), C12B(H12G,H12H)
5.c Aromatic/amide H refined with riding coordinates:
C1(H1), C2(H2), C3(H3), C4(H4), C1'(H1'), C2'(H2'), C3'(H3'), C4'(H4')
;
_shelx_res_file
;
202405199b_auto.res created by SHELXL-2014/7
TITL 202405199b_auto_a.res in P-1
CELL 1.54184 6.5464 13.7584 16.2007 67.284 85.636 87.696
ZERR 4 0.0004 0.0008 0.001 0.006 0.005 0.005
LATT 1
SFAC C H F N S
UNIT 52 52 12 8 4
DFIX 1.64 C10' C9'
DFIX 1.64 C10' C11'
DFIX 1.54 C10B C11'
DFIX 1.54 C9'A C10B
DFIX 1.78 S1'A C13B
DFIX 2.5 F2'A S1'A
DFIX 1.54 C11A C10A
DFIX 1.78 S1A C12A
DFIX 1.54 C8A C12A
DFIX 1.54 C10 C9
DFIX 1.54 C9A C8A
DFIX 1.54 C10A C9A
DFIX 2.2 S1A F2A
DFIX 2.3 S1A F3A
DFIX 1.45 C11A N2
DFIX 2.3 S1'A F3'A
DFIX 2.3 S1'A F1'A
DFIX 1.8 F3A F2A
DFIX 1.8 F3A F1A
DFIX 1.35 C13B F1'A C13B F3'A C13B F2'A
DFIX 1.35 C13A F3A
DFIX 1.68 C8' C12'
DFIX 1.54 C8'A C12B
DFIX 1.78 C9' C8'
DFIX 1.54 C9'A C8'A
DFIX 1.78 S1' C12'
DFIX 1.54 C7' C8'A
SADI 0.04 F3' F1' F3' F2' F1' F2'
SADI C13' F3' C13' F1' C13' F2'
SADI 0.04 F1'A F3'A F1'A F2'A F3'A F2'A
SADI C13B F1'A C13B F3'A C13B F2'A
SADI 0.04 F3A F2A F3A F1A F2A F1A
SADI C13A F3A C13A F2A C13A F1A
SADI 0.04 F1 F2 F1 F3 F2 F3
SADI C13 F1 C13 F2 C13 F3
ISOR 0.01 0.02 C10B C10' C9'A C9'
ISOR 0.01 0.02 F2'A F2' F3' F3'A
ISOR 0.01 0.02 C8' C8'A
EADP C10' C10B
EADP C9' C9'A
EADP C8' C8'A
EADP C12' C12B
EADP S1' S1'A
EADP C13' C13B
EADP F1' F1'A
EADP F3' F3'A
EADP F2' F2'A
EADP C11 C11A
EADP C10 C10A
EADP C9 C9A
EADP C8 C8A
EADP C12 C12A
EADP S1 S1A
EADP C13 C13A
EADP F3 F3A
EADP F2 F2A
EADP F1 F1A
L.S. 54 0 0
PLAN 20
SIZE 0.04 0.11 0.17
BOND $H
list 4
fmap 2
acta
SHEL 999 0.837
OMIT 0 -1 5
OMIT 0 2 7
OMIT -1 -5 2
OMIT -1 4 3
OMIT 2 3 3
OMIT 1 7 7
OMIT 0 7 5
OMIT 0 0 5
OMIT -1 5 2
OMIT -1 2 4
OMIT -1 1 3
OMIT 3 -1 3
OMIT 0 3 8
OMIT -4 2 2
REM
REM
REM
WGHT 0.230000
FVAR 0.54671 0.82353 0.83233
PART 1
S1 5 0.470262 0.701601 0.387912 31.00000 0.12224 0.12039 =
0.09068 -0.05802 0.01513 0.00092
PART 0
PART 2
S1A 5 0.455858 0.670980 0.423665 -31.00000 0.12224 0.12039 =
0.09068 -0.05802 0.01513 0.00092
PART 0
PART 1
F1 3 0.074398 0.670230 0.394873 31.00000 0.11245 0.14561 =
0.15102 -0.06567 -0.01417 0.02380
PART 0
PART 2
F1A 3 0.084770 0.646153 0.447346 -31.00000 0.11245 0.14561 =
0.15102 -0.06567 -0.01417 0.02380
PART 0
PART 1
F2 3 0.273258 0.544844 0.385466 31.00000 0.18494 0.11057 =
0.17031 -0.09842 -0.02518 0.01847
PART 0
PART 2
F2A 3 0.236365 0.578093 0.386820 -31.00000 0.18494 0.11057 =
0.17031 -0.09842 -0.02518 0.01847
PART 0
PART 1
F3 3 0.224934 0.568942 0.510931 31.00000 0.26418 0.13096 =
0.10702 -0.03993 0.00605 -0.05551
PART 0
PART 2
F3A 3 0.239737 0.534395 0.506981 -31.00000 0.26418 0.13096 =
0.10702 -0.03993 0.00605 -0.05551
PART 0
N1 4 0.244597 0.889428 0.560405 11.00000 0.07315 0.10632 =
0.09949 -0.05836 -0.02592 0.02526
N2 4 0.517117 0.847035 0.641985 11.00000 0.06195 0.07262 =
0.07172 -0.02820 -0.01186 0.00425
C1 1 0.428216 0.956263 0.735313 11.00000 0.10312 0.07970 =
0.07931 -0.03147 -0.01821 -0.00519
AFIX 43
H1 2 0.541900 0.938655 0.769559 11.00000 -1.20000
AFIX 0
C2 1 0.279044 1.022707 0.746792 11.00000 0.13231 0.08162 =
0.08032 -0.04047 -0.00195 -0.00621
AFIX 43
H2 2 0.290858 1.050498 0.790194 11.00000 -1.20000
AFIX 0
C3 1 0.108899 1.050156 0.695083 11.00000 0.10852 0.07111 =
0.08545 -0.03033 0.00878 0.00841
AFIX 43
H3 2 0.010247 1.095811 0.704818 11.00000 -1.20000
AFIX 0
C4 1 0.083853 1.011346 0.630245 11.00000 0.08066 0.07511 =
0.08165 -0.02764 0.00112 0.00760
AFIX 43
H4 2 -0.028923 1.030409 0.595467 11.00000 -1.20000
AFIX 0
C5 1 0.234092 0.942197 0.618517 11.00000 0.06655 0.06925 =
0.07572 -0.03063 -0.00394 -0.00010
C6 1 0.402998 0.915457 0.669513 11.00000 0.06899 0.06209 =
0.06889 -0.02012 -0.00245 -0.00735
C7 1 0.410584 0.832684 0.578364 11.00000 0.07062 0.09630 =
0.07700 -0.04168 -0.01382 0.01481
PART 1
C8 1 0.480242 0.751212 0.540328 31.00000 0.08366 0.07949 =
0.07429 -0.03056 0.00207 0.01065
AFIX 13
H8 2 0.409184 0.685436 0.576323 31.00000 -1.20000
AFIX 0
PART 0
PART 2
C8A 1 0.538967 0.805927 0.503822 -31.00000 0.08366 0.07949 =
0.07429 -0.03056 0.00207 0.01065
AFIX 13
H8A 2 0.610801 0.861952 0.453822 -31.00000 -1.20000
AFIX 0
PART 0
PART 1
C9 1 0.713201 0.729941 0.549726 31.00000 0.07493 0.07941 =
0.09569 -0.02954 0.00730 0.01857
AFIX 23
H9A 2 0.753127 0.670531 0.533662 31.00000 -1.20000
H9B 2 0.788081 0.791048 0.508698 31.00000 -1.20000
AFIX 0
PART 0
PART 2
C9A 1 0.661768 0.713937 0.569550 -31.00000 0.07493 0.07941 =
0.09569 -0.02954 0.00730 0.01857
AFIX 23
H9AA 2 0.570363 0.669690 0.618448 -31.00000 -1.20000
H9AB 2 0.724308 0.671179 0.538662 -31.00000 -1.20000
AFIX 0
PART 0
PART 1
C10 1 0.767929 0.706847 0.643625 31.00000 0.07557 0.08484 =
0.11304 -0.02915 -0.01446 0.02024
AFIX 23
H10A 2 0.913357 0.690908 0.647966 31.00000 -1.20000
H10B 2 0.694199 0.645147 0.684359 31.00000 -1.20000
AFIX 0
PART 0
PART 2
C10A 1 0.828301 0.757736 0.606766 -31.00000 0.07557 0.08484 =
0.11304 -0.02915 -0.01446 0.02024
AFIX 23
H10C 2 0.891552 0.819768 0.561134 -31.00000 -1.20000
H10D 2 0.933087 0.705221 0.633049 -31.00000 -1.20000
AFIX 0
PART 0
PART 1
C11 1 0.716219 0.800100 0.672401 31.00000 0.06441 0.08674 =
0.10893 -0.03737 -0.02482 0.00626
AFIX 23
H11A 2 0.713689 0.775644 0.737212 31.00000 -1.20000
H11B 2 0.821604 0.853025 0.647153 31.00000 -1.20000
AFIX 0
PART 0
PART 2
C11A 1 0.697693 0.785004 0.678683 -31.00000 0.06441 0.08674 =
0.10893 -0.03737 -0.02482 0.00626
AFIX 23
H11C 2 0.655610 0.720373 0.727891 -31.00000 -1.20000
H11D 2 0.780023 0.824274 0.702186 -31.00000 -1.20000
AFIX 0
PART 0
PART 1
C12 1 0.410624 0.788595 0.444105 31.00000 0.12160 0.06404 =
0.06206 -0.01803 -0.00123 0.00704
AFIX 23
H12A 2 0.473135 0.856070 0.408863 31.00000 -1.20000
H12B 2 0.263413 0.799851 0.446127 31.00000 -1.20000
AFIX 0
PART 0
PART 2
C12A 1 0.359497 0.747701 0.486019 -31.00000 0.12160 0.06404 =
0.06206 -0.01803 -0.00123 0.00704
AFIX 23
H12C 2 0.259081 0.798594 0.452505 -31.00000 -1.20000
H12D 2 0.292830 0.702087 0.542576 -31.00000 -1.20000
AFIX 0
PART 0
PART 1
C13 1 0.241170 0.614811 0.423254 31.00000 0.13471 0.09300 =
0.09409 -0.05786 -0.02208 0.00550
PART 0
PART 2
C13A 1 0.278684 0.624900 0.439350 -31.00000 0.13471 0.09300 =
0.09409 -0.05786 -0.02208 0.00550
PART 0
PART 1
S1' 5 0.074812 0.811067 0.140875 21.00000 0.14438 0.10030 =
0.20384 -0.09063 0.05804 -0.00936
PART 0
PART 2
S1'A 5 0.222367 0.789970 0.174937 -21.00000 0.14438 0.10030 =
0.20384 -0.09063 0.05804 -0.00936
PART 0
PART 1
F1' 3 0.294653 0.913034 -0.001821 21.00000 0.22270 0.16142 =
0.13392 -0.04392 0.03826 -0.03565
PART 0
PART 2
F1'A 3 0.069463 0.899157 0.054019 -21.00000 0.22270 0.16142 =
0.13392 -0.04392 0.03826 -0.03565
PART 0
PART 1
F2' 3 0.472685 0.844566 0.108929 21.00000 0.14050 0.15974 =
0.27737 -0.11914 -0.03347 0.00308
PART 0
PART 2
F2'A 3 0.433417 0.885848 0.035813 -21.00000 0.14050 0.15974 =
0.27737 -0.11914 -0.03347 0.00308
PART 0
PART 1
F3' 3 0.271017 0.979284 0.093742 21.00000 0.22406 0.12067 =
0.25510 -0.12565 0.04444 -0.02713
PART 0
PART 2
F3'A 3 0.287344 0.964191 0.130167 -21.00000 0.22406 0.12067 =
0.25510 -0.12565 0.04444 -0.02713
PART 0
N1' 4 0.238419 0.504330 0.096402 11.00000 0.06518 0.07793 =
0.09298 -0.03855 0.01765 -0.01087
N2' 4 -0.071381 0.440555 0.157159 11.00000 0.04907 0.08309 =
0.07254 -0.02547 0.00424 -0.00675
C1' 1 -0.036264 0.265771 0.139335 11.00000 0.08508 0.08227 =
0.08206 -0.02492 -0.00505 -0.02216
AFIX 43
H1' 2 -0.164536 0.239171 0.164837 11.00000 -1.20000
AFIX 0
C2' 1 0.101316 0.209188 0.107940 11.00000 0.13426 0.07311 =
0.08662 -0.03399 -0.00578 -0.01745
AFIX 43
H2' 2 0.066059 0.142472 0.112339 11.00000 -1.20000
AFIX 0
C3' 1 0.291723 0.248328 0.069764 11.00000 0.11392 0.08491 =
0.07775 -0.03917 -0.00264 0.01070
AFIX 43
H3' 2 0.381648 0.206970 0.049569 11.00000 -1.20000
AFIX 0
C4' 1 0.351980 0.346109 0.060770 11.00000 0.07635 0.08817 =
0.06884 -0.03147 0.00926 0.00245
AFIX 43
H4' 2 0.480122 0.371820 0.034271 11.00000 -1.20000
AFIX 0
C5' 1 0.215397 0.406120 0.092552 11.00000 0.06443 0.07082 =
0.05876 -0.02399 0.00529 -0.00570
C6' 1 0.023226 0.365126 0.131640 11.00000 0.05741 0.07266 =
0.05732 -0.01959 -0.00262 -0.00792
C7' 1 0.063871 0.520566 0.135431 11.00000 0.06736 0.07511 =
0.08074 -0.03424 0.00926 -0.00034
PART 1
C8' 1 0.019128 0.611908 0.163408 21.00000 0.10251 0.08971 =
0.11187 -0.05150 0.02676 -0.00317
AFIX 13
H8' 2 0.094067 0.586614 0.218071 21.00000 -1.20000
AFIX 0
PART 0
PART 2
C8'A 1 -0.033097 0.629734 0.123720 -21.00000 0.10251 0.08971 =
0.11187 -0.05150 0.02676 -0.00317
AFIX 13
H8'A 2 -0.061182 0.670439 0.061007 -21.00000 -1.20000
AFIX 0
PART 0
PART 1
C9' 1 -0.187508 0.612059 0.204615 21.00000 0.10651 0.12289 =
0.13870 -0.07536 0.01666 0.01137
AFIX 23
H9'A 2 -0.256945 0.674470 0.165211 21.00000 -1.20000
H9'B 2 -0.172548 0.622184 0.259864 21.00000 -1.20000
AFIX 0
PART 0
PART 2
C9'A 1 -0.228833 0.603431 0.182705 -21.00000 0.10651 0.12289 =
0.13870 -0.07536 0.01666 0.01137
AFIX 23
H9'C 2 -0.338299 0.611235 0.143404 -21.00000 -1.20000
H9'D 2 -0.250440 0.658233 0.206323 -21.00000 -1.20000
AFIX 0
PART 0
PART 1
C10' 1 -0.328755 0.523926 0.226719 21.00000 0.09368 0.12178 =
0.13772 -0.05327 0.03617 0.00253
AFIX 23
H10E 2 -0.454782 0.553331 0.198513 21.00000 -1.20000
H10F 2 -0.361097 0.497704 0.290965 21.00000 -1.20000
AFIX 0
PART 0
PART 2
C10B 1 -0.264104 0.497770 0.262757 -21.00000 0.09368 0.12178 =
0.13772 -0.05327 0.03617 0.00253
AFIX 23
H10G 2 -0.391230 0.497023 0.297900 -21.00000 -1.20000
H10H 2 -0.150317 0.477235 0.301230 -21.00000 -1.20000
AFIX 0
PART 0
C11' 1 -0.274478 0.431332 0.204268 11.00000 0.05429 0.13334 =
0.09632 -0.03701 0.01073 -0.00412
PART 1
AFIX 23
H11E 2 -0.277041 0.368528 0.259032 21.00000 -1.20000
H11F 2 -0.376239 0.423443 0.166860 21.00000 -1.20000
AFIX 23
PART 0
PART 2
H11G 2 -0.304065 0.358317 0.241576 -21.00000 -1.20000
H11H 2 -0.379849 0.458809 0.161882 -21.00000 -1.20000
AFIX 0
PART 0
PART 1
C12' 1 0.148136 0.702414 0.109647 21.00000 0.14041 0.08521 =
0.17646 -0.07142 0.05512 -0.02127
AFIX 23
H12E 2 0.130654 0.721415 0.046367 21.00000 -1.20000
H12F 2 0.291187 0.684368 0.120234 21.00000 -1.20000
AFIX 0
PART 0
PART 2
C12B 1 0.152056 0.674419 0.150394 -21.00000 0.14041 0.08521 =
0.17646 -0.07142 0.05512 -0.02127
AFIX 23
H12G 2 0.256432 0.675602 0.104199 -21.00000 -1.20000
H12H 2 0.190823 0.615787 0.203760 -21.00000 -1.20000
AFIX 0
PART 0
PART 1
C13' 1 0.286417 0.884270 0.089267 21.00000 0.16680 0.09764 =
0.18084 -0.09017 0.01774 -0.00607
PART 0
PART 2
C13B 1 0.260739 0.908047 0.078525 -21.00000 0.16680 0.09764 =
0.18084 -0.09017 0.01774 -0.00607
HKLF 4
REM 202405199b_auto_a.res in P-1
REM R1 = 0.1078 for 3273 Fo > 4sig(Fo) and 0.1330 for all 4763 data
REM 402 parameters refined using 113 restraints
END
WGHT 0.2000 0.0000
REM Highest difference peak 0.679, deepest hole -0.433, 1-sigma level 0.073
Q1 1 0.2150 0.7178 0.4765 11.00000 0.05 0.68
Q2 1 0.3095 0.7458 0.0896 11.00000 0.05 0.61
Q3 1 0.1044 0.8388 0.0693 11.00000 0.05 0.58
Q4 1 0.3124 0.7868 0.1472 11.00000 0.05 0.42
Q5 1 0.3721 0.8247 0.1948 11.00000 0.05 0.40
Q6 1 -0.1604 0.5659 0.2431 11.00000 0.05 0.38
Q7 1 0.4527 0.8737 0.5470 11.00000 0.05 0.32
Q8 1 0.1865 0.6596 0.3635 11.00000 0.05 0.32
Q9 1 0.1229 0.5233 0.5032 11.00000 0.05 0.27
Q10 1 0.4169 0.5585 0.4797 11.00000 0.05 0.27
Q11 1 0.3080 0.9364 0.5229 11.00000 0.05 0.26
Q12 1 -0.1931 0.6868 0.2141 11.00000 0.05 0.26
Q13 1 0.1967 0.8801 0.5589 11.00000 0.05 0.25
Q14 1 0.0686 0.3936 0.1012 11.00000 0.05 0.25
Q15 1 0.5607 0.8473 0.6103 11.00000 0.05 0.25
Q16 1 -0.3271 0.5044 0.1827 11.00000 0.05 0.25
Q17 1 0.7879 0.7874 0.6232 11.00000 0.05 0.24
Q18 1 -0.3408 0.5539 0.1801 11.00000 0.05 0.24
Q19 1 -0.0424 0.5011 0.1307 11.00000 0.05 0.23
Q20 1 -0.2041 0.4558 0.1622 11.00000 0.05 0.23
;
_shelx_res_checksum 14794
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.721
_oxdiff_exptl_absorpt_empirical_full_min 0.737
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.4703(4) 0.7016(3) 0.3879(2) 0.1071(8) Uani 0.832(7) 1 d . . P A 1
S1A S 0.456(3) 0.6710(13) 0.4237(10) 0.1071(8) Uani 0.168(7) 1 d D . P A 2
F1 F 0.0744(10) 0.6702(6) 0.3949(5) 0.134(2) Uani 0.832(7) 1 d D . P A 1
F1A F 0.085(5) 0.646(3) 0.447(3) 0.134(2) Uani 0.168(7) 1 d D . P A 2
F2 F 0.2733(12) 0.5448(5) 0.3855(5) 0.142(2) Uani 0.832(7) 1 d D . P A 1
F2A F 0.236(5) 0.578(2) 0.387(2) 0.142(2) Uani 0.168(7) 1 d D . P A 2
F3 F 0.2249(17) 0.5689(6) 0.5109(5) 0.169(3) Uani 0.832(7) 1 d D . P A 1
F3A F 0.240(6) 0.534(2) 0.507(2) 0.169(3) Uani 0.168(7) 1 d D . P A 2
N1 N 0.2446(7) 0.8894(4) 0.5604(3) 0.0869(12) Uani 1 1 d . . . . .
N2 N 0.5171(6) 0.8470(3) 0.6420(2) 0.0684(9) Uani 1 1 d D . . . .
C1 C 0.4282(10) 0.9563(4) 0.7353(4) 0.0863(14) Uani 1 1 d . . . . .
H1 H 0.5419 0.9387 0.7696 0.104 Uiso 1 1 calc R . . . .
C2 C 0.2790(11) 1.0227(4) 0.7468(4) 0.0954(17) Uani 1 1 d . . . . .
H2 H 0.2909 1.0505 0.7902 0.114 Uiso 1 1 calc R . . . .
C3 C 0.1089(10) 1.0502(4) 0.6951(4) 0.0894(15) Uani 1 1 d . . . . .
H3 H 0.0102 1.0958 0.7048 0.107 Uiso 1 1 calc R . . . .
C4 C 0.0839(8) 1.0113(4) 0.6302(3) 0.0805(12) Uani 1 1 d . . . . .
H4 H -0.0289 1.0304 0.5955 0.097 Uiso 1 1 calc R . . . .
C5 C 0.2341(7) 0.9422(3) 0.6185(3) 0.0697(10) Uani 1 1 d . . . . .
C6 C 0.4030(7) 0.9155(3) 0.6695(3) 0.0681(10) Uani 1 1 d . . . . .
C7 C 0.4106(8) 0.8327(4) 0.5784(3) 0.0787(12) Uani 1 1 d . . . . .
C8 C 0.4802(10) 0.7512(5) 0.5403(4) 0.0796(16) Uani 0.832(7) 1 d . . P A 1
H8 H 0.4092 0.6854 0.5763 0.096 Uiso 0.832(7) 1 calc R . P A 1
C8A C 0.539(4) 0.806(3) 0.504(2) 0.0796(16) Uani 0.168(7) 1 d D . P A 2
H8A H 0.6108 0.8620 0.4538 0.096 Uiso 0.168(7) 1 calc R . P A 2
C9 C 0.7132(11) 0.7299(7) 0.5497(5) 0.086(2) Uani 0.832(7) 1 d D . P A 1
H9A H 0.7531 0.6705 0.5337 0.103 Uiso 0.832(7) 1 calc R . P A 1
H9B H 0.7881 0.7910 0.5087 0.103 Uiso 0.832(7) 1 calc R . P A 1
C9A C 0.662(6) 0.714(3) 0.570(3) 0.086(2) Uani 0.168(7) 1 d D . P A 2
H9AA H 0.5704 0.6697 0.6184 0.103 Uiso 0.168(7) 1 calc R . P A 2
H9AB H 0.7243 0.6712 0.5387 0.103 Uiso 0.168(7) 1 calc R . P A 2
C10 C 0.7679(12) 0.7068(6) 0.6436(5) 0.094(2) Uani 0.832(7) 1 d D . P A 1
H10A H 0.9134 0.6909 0.6480 0.113 Uiso 0.832(7) 1 calc R . P A 1
H10B H 0.6942 0.6451 0.6844 0.113 Uiso 0.832(7) 1 calc R . P A 1
C10A C 0.828(6) 0.758(3) 0.607(3) 0.094(2) Uani 0.168(7) 1 d D . P A 2
H10C H 0.8916 0.8198 0.5611 0.113 Uiso 0.168(7) 1 calc R . P A 2
H10D H 0.9331 0.7052 0.6330 0.113 Uiso 0.168(7) 1 calc R . P A 2
C11 C 0.7162(19) 0.8001(14) 0.6724(8) 0.086(3) Uani 0.832(7) 1 d . . P A 1
H11A H 0.7137 0.7756 0.7372 0.103 Uiso 0.832(7) 1 calc R . P A 1
H11B H 0.8216 0.8530 0.6472 0.103 Uiso 0.832(7) 1 calc R . P A 1
C11A C 0.698(11) 0.785(9) 0.679(4) 0.086(3) Uani 0.168(7) 1 d D . P A 2
H11C H 0.6556 0.7204 0.7279 0.103 Uiso 0.168(7) 1 calc R . P A 2
H11D H 0.7800 0.8243 0.7022 0.103 Uiso 0.168(7) 1 calc R . P A 2
C12 C 0.4106(12) 0.7886(5) 0.4441(4) 0.0850(18) Uani 0.832(7) 1 d . . P A 1
H12A H 0.4731 0.8561 0.4089 0.102 Uiso 0.832(7) 1 calc R . P A 1
H12B H 0.2634 0.7999 0.4461 0.102 Uiso 0.832(7) 1 calc R . P A 1
C12A C 0.359(5) 0.748(2) 0.486(2) 0.0850(18) Uani 0.168(7) 1 d D . P A 2
H12C H 0.2591 0.7986 0.4525 0.102 Uiso 0.168(7) 1 calc R . P A 2
H12D H 0.2928 0.7021 0.5426 0.102 Uiso 0.168(7) 1 calc R . P A 2
C13 C 0.2412(14) 0.6148(6) 0.4233(5) 0.100(2) Uani 0.832(7) 1 d D . P A 1
C13A C 0.279(6) 0.625(2) 0.4394(19) 0.100(2) Uani 0.168(7) 1 d D . P A 2
S1' S 0.0748(6) 0.8111(2) 0.1409(3) 0.1434(13) Uani 0.824(4) 1 d D . P B 1
S1'A S 0.222(3) 0.7900(9) 0.1749(11) 0.1434(13) Uani 0.176(4) 1 d D . P B 2
F1' F 0.2947(16) 0.9130(7) -0.0018(5) 0.178(3) Uani 0.824(4) 1 d D . P B 1
F1'A F 0.069(5) 0.899(3) 0.0540(17) 0.178(3) Uani 0.176(4) 1 d D . P B 2
F2' F 0.4727(12) 0.8446(7) 0.1089(8) 0.181(3) Uani 0.824(4) 1 d D U P B 1
F2'A F 0.433(5) 0.886(3) 0.036(2) 0.181(3) Uani 0.176(4) 1 d D U P B 2
F3' F 0.271(2) 0.9793(6) 0.0937(7) 0.186(4) Uani 0.824(4) 1 d D U P B 1
F3'A F 0.287(9) 0.964(2) 0.130(3) 0.186(4) Uani 0.176(4) 1 d D U P B 2
N1' N 0.2384(6) 0.5043(3) 0.0964(3) 0.0779(10) Uani 1 1 d . . . . .
N2' N -0.0714(5) 0.4406(3) 0.1572(2) 0.0699(9) Uani 1 1 d . . . . .
C1' C -0.0363(9) 0.2658(4) 0.1393(4) 0.0846(13) Uani 1 1 d . . . . .
H1' H -0.1645 0.2392 0.1648 0.101 Uiso 1 1 calc R . . . .
C2' C 0.1013(11) 0.2092(4) 0.1079(4) 0.0966(17) Uani 1 1 d . . . . .
H2' H 0.0661 0.1425 0.1123 0.116 Uiso 1 1 calc R . . . .
C3' C 0.2917(10) 0.2483(4) 0.0698(4) 0.0903(15) Uani 1 1 d . . . . .
H3' H 0.3816 0.2070 0.0496 0.108 Uiso 1 1 calc R . . . .
C4' C 0.3520(8) 0.3461(4) 0.0608(3) 0.0783(12) Uani 1 1 d . . . . .
H4' H 0.4801 0.3718 0.0343 0.094 Uiso 1 1 calc R . . . .
C5' C 0.2154(7) 0.4061(3) 0.0926(3) 0.0653(10) Uani 1 1 d . . . . .
C6' C 0.0232(6) 0.3651(3) 0.1316(3) 0.0640(9) Uani 1 1 d . . . . .
C7' C 0.0639(7) 0.5206(4) 0.1354(3) 0.0739(11) Uani 1 1 d D . . . .
C8' C 0.0191(14) 0.6119(6) 0.1634(6) 0.099(2) Uani 0.824(4) 1 d D U P B 1
H8' H 0.0941 0.5866 0.2181 0.119 Uiso 0.824(4) 1 calc R . P B 1
C8'A C -0.033(6) 0.630(2) 0.124(3) 0.099(2) Uani 0.176(4) 1 d D U P B 2
H8'A H -0.0612 0.6704 0.0610 0.119 Uiso 0.176(4) 1 calc R . P B 2
C9' C -0.1875(15) 0.6121(9) 0.2046(8) 0.117(3) Uani 0.824(4) 1 d D U P B 1
H9'A H -0.2569 0.6745 0.1652 0.140 Uiso 0.824(4) 1 calc R . P B 1
H9'B H -0.1725 0.6222 0.2599 0.140 Uiso 0.824(4) 1 calc R . P B 1
C9'A C -0.229(8) 0.603(4) 0.183(3) 0.117(3) Uani 0.176(4) 1 d D U P B 2
H9'C H -0.3383 0.6112 0.1434 0.140 Uiso 0.176(4) 1 calc R . P B 2
H9'D H -0.2504 0.6582 0.2063 0.140 Uiso 0.176(4) 1 calc R . P B 2
C10' C -0.3288(14) 0.5239(7) 0.2267(8) 0.119(3) Uani 0.824(4) 1 d D U P B 1
H10E H -0.4548 0.5533 0.1985 0.143 Uiso 0.824(4) 1 calc R . P B 1
H10F H -0.3611 0.4977 0.2910 0.143 Uiso 0.824(4) 1 calc R . P B 1
C10B C -0.264(8) 0.498(3) 0.263(3) 0.119(3) Uani 0.176(4) 1 d D U P B 2
H10G H -0.3912 0.4970 0.2979 0.143 Uiso 0.176(4) 1 calc R . P B 2
H10H H -0.1503 0.4772 0.3012 0.143 Uiso 0.176(4) 1 calc R . P B 2
C11' C -0.2745(8) 0.4313(6) 0.2043(4) 0.0976(17) Uani 1 1 d D . . . .
H11E H -0.2770 0.3685 0.2590 0.117 Uiso 0.824(4) 1 calc R . P B 1
H11F H -0.3762 0.4234 0.1669 0.117 Uiso 0.824(4) 1 calc R . P B 1
H11G H -0.3041 0.3583 0.2416 0.117 Uiso 0.176(4) 1 calc R . P B 2
H11H H -0.3798 0.4588 0.1619 0.117 Uiso 0.176(4) 1 calc R . P B 2
C12' C 0.148(2) 0.7024(8) 0.1096(9) 0.131(4) Uani 0.824(4) 1 d D . P B 1
H12E H 0.1307 0.7214 0.0464 0.157 Uiso 0.824(4) 1 calc R . P B 1
H12F H 0.2912 0.6844 0.1202 0.157 Uiso 0.824(4) 1 calc R . P B 1
C12B C 0.152(9) 0.674(5) 0.150(5) 0.131(4) Uani 0.176(4) 1 d D . P B 2
H12G H 0.2564 0.6756 0.1042 0.157 Uiso 0.176(4) 1 calc R . P B 2
H12H H 0.1908 0.6158 0.2038 0.157 Uiso 0.176(4) 1 calc R . P B 2
C13' C 0.2864(19) 0.8843(8) 0.0893(8) 0.139(3) Uani 0.824(4) 1 d D . P B 1
C13B C 0.261(5) 0.908(2) 0.0785(18) 0.139(3) Uani 0.176(4) 1 d D . P B 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.1222(15) 0.1204(19) 0.0907(17) -0.0580(15) 0.0151(13) 0.0009(13)
S1A 0.1222(15) 0.1204(19) 0.0907(17) -0.0580(15) 0.0151(13) 0.0009(13)
F1 0.112(3) 0.146(5) 0.151(5) -0.066(5) -0.014(4) 0.024(3)
F1A 0.112(3) 0.146(5) 0.151(5) -0.066(5) -0.014(4) 0.024(3)
F2 0.185(6) 0.111(4) 0.170(4) -0.098(4) -0.025(4) 0.018(4)
F2A 0.185(6) 0.111(4) 0.170(4) -0.098(4) -0.025(4) 0.018(4)
F3 0.264(8) 0.131(5) 0.107(3) -0.040(4) 0.006(4) -0.056(5)
F3A 0.264(8) 0.131(5) 0.107(3) -0.040(4) 0.006(4) -0.056(5)
N1 0.073(2) 0.106(3) 0.099(3) -0.058(2) -0.026(2) 0.025(2)
N2 0.0620(19) 0.073(2) 0.0717(19) -0.0282(16) -0.0119(15) 0.0042(16)
C1 0.103(4) 0.080(3) 0.079(3) -0.031(2) -0.018(3) -0.005(3)
C2 0.132(5) 0.082(3) 0.080(3) -0.040(2) -0.002(3) -0.006(3)
C3 0.109(4) 0.071(3) 0.085(3) -0.030(2) 0.009(3) 0.008(3)
C4 0.081(3) 0.075(3) 0.082(3) -0.028(2) 0.001(2) 0.008(2)
C5 0.067(2) 0.069(2) 0.076(2) -0.0306(19) -0.0039(19) -0.0001(19)
C6 0.069(2) 0.062(2) 0.069(2) -0.0201(18) -0.0025(18) -0.0073(18)
C7 0.071(3) 0.096(3) 0.077(3) -0.042(2) -0.014(2) 0.015(2)
C8 0.084(4) 0.079(4) 0.074(3) -0.031(3) 0.002(3) 0.011(3)
C8A 0.084(4) 0.079(4) 0.074(3) -0.031(3) 0.002(3) 0.011(3)
C9 0.075(5) 0.079(4) 0.096(5) -0.030(3) 0.007(3) 0.019(3)
C9A 0.075(5) 0.079(4) 0.096(5) -0.030(3) 0.007(3) 0.019(3)
C10 0.076(4) 0.085(5) 0.113(5) -0.029(4) -0.014(4) 0.020(3)
C10A 0.076(4) 0.085(5) 0.113(5) -0.029(4) -0.014(4) 0.020(3)
C11 0.064(4) 0.087(7) 0.109(4) -0.037(4) -0.025(3) 0.006(5)
C11A 0.064(4) 0.087(7) 0.109(4) -0.037(4) -0.025(3) 0.006(5)
C12 0.122(5) 0.064(3) 0.062(3) -0.018(3) -0.001(3) 0.007(3)
C12A 0.122(5) 0.064(3) 0.062(3) -0.018(3) -0.001(3) 0.007(3)
C13 0.135(7) 0.093(4) 0.094(4) -0.058(4) -0.022(4) 0.006(4)
C13A 0.135(7) 0.093(4) 0.094(4) -0.058(4) -0.022(4) 0.006(4)
S1' 0.144(2) 0.1003(14) 0.204(3) -0.0906(18) 0.058(2) -0.0094(15)
S1'A 0.144(2) 0.1003(14) 0.204(3) -0.0906(18) 0.058(2) -0.0094(15)
F1' 0.223(9) 0.161(6) 0.134(5) -0.044(4) 0.038(5) -0.036(6)
F1'A 0.223(9) 0.161(6) 0.134(5) -0.044(4) 0.038(5) -0.036(6)
F2' 0.140(5) 0.160(6) 0.277(9) -0.119(6) -0.033(6) 0.003(4)
F2'A 0.140(5) 0.160(6) 0.277(9) -0.119(6) -0.033(6) 0.003(4)
F3' 0.224(7) 0.121(4) 0.255(9) -0.126(5) 0.044(7) -0.027(4)
F3'A 0.224(7) 0.121(4) 0.255(9) -0.126(5) 0.044(7) -0.027(4)
N1' 0.065(2) 0.078(2) 0.093(2) -0.0386(19) 0.0177(18) -0.0109(17)
N2' 0.0491(17) 0.083(2) 0.0725(19) -0.0255(17) 0.0042(14) -0.0067(16)
C1' 0.085(3) 0.082(3) 0.082(3) -0.025(2) -0.005(2) -0.022(2)
C2' 0.134(5) 0.073(3) 0.087(3) -0.034(3) -0.006(3) -0.017(3)
C3' 0.114(4) 0.085(3) 0.078(3) -0.039(2) -0.003(3) 0.011(3)
C4' 0.076(3) 0.088(3) 0.069(2) -0.031(2) 0.009(2) 0.002(2)
C5' 0.064(2) 0.071(2) 0.0588(19) -0.0240(17) 0.0053(16) -0.0057(18)
C6' 0.057(2) 0.073(2) 0.0573(19) -0.0196(17) -0.0026(15) -0.0079(17)
C7' 0.067(2) 0.075(3) 0.081(3) -0.034(2) 0.009(2) 0.000(2)
C8' 0.103(4) 0.090(4) 0.112(5) -0.052(4) 0.027(4) -0.003(3)
C8'A 0.103(4) 0.090(4) 0.112(5) -0.052(4) 0.027(4) -0.003(3)
C9' 0.107(5) 0.123(5) 0.139(6) -0.075(4) 0.017(4) 0.011(4)
C9'A 0.107(5) 0.123(5) 0.139(6) -0.075(4) 0.017(4) 0.011(4)
C10' 0.094(5) 0.122(5) 0.138(6) -0.053(4) 0.036(4) 0.003(4)
C10B 0.094(5) 0.122(5) 0.138(6) -0.053(4) 0.036(4) 0.003(4)
C11' 0.054(3) 0.133(5) 0.096(3) -0.037(3) 0.011(2) -0.004(3)
C12' 0.140(7) 0.085(7) 0.176(11) -0.071(8) 0.055(8) -0.021(5)
C12B 0.140(7) 0.085(7) 0.176(11) -0.071(8) 0.055(8) -0.021(5)
C13' 0.167(9) 0.098(6) 0.181(9) -0.090(6) 0.018(7) -0.006(6)
C13B 0.167(9) 0.098(6) 0.181(9) -0.090(6) 0.018(7) -0.006(6)
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'
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C12 S1 C13 101.3(3) . . ?
C13A S1A C12A 89.0(19) . . ?
C7 N1 C5 104.8(4) . . ?
C6 N2 C7 106.2(4) . . ?
C6 N2 C11 127.3(7) . . ?
C6 N2 C11A 130(3) . . ?
C7 N2 C11 126.5(7) . . ?
C7 N2 C11A 123(4) . . ?
C2 C1 H1 121.4 . . ?
C2 C1 C6 117.2(5) . . ?
C6 C1 H1 121.4 . . ?
C1 C2 H2 119.2 . . ?
C1 C2 C3 121.7(5) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.5(5) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 121.3 . . ?
C3 C4 C5 117.4(5) . . ?
C5 C4 H4 121.3 . . ?
N1 C5 C4 129.5(4) . . ?
C6 C5 N1 109.5(4) . . ?
C6 C5 C4 121.0(4) . . ?
N2 C6 C1 132.7(4) . . ?
N2 C6 C5 106.1(4) . . ?
C5 C6 C1 121.2(5) . . ?
N1 C7 N2 113.4(4) . . ?
N1 C7 C8 125.8(5) . . ?
N1 C7 C8A 121.0(11) . . ?
N2 C7 C8 120.7(5) . . ?
N2 C7 C8A 116.9(11) . . ?
C7 C8 H8 107.7 . . ?
C7 C8 C9 109.8(6) . . ?
C7 C8 C12 108.1(5) . . ?
C9 C8 H8 107.7 . . ?
C12 C8 H8 107.7 . . ?
C12 C8 C9 115.5(6) . . ?
C7 C8A H8A 120.0 . . ?
C9A C8A C7 96(3) . . ?
C9A C8A H8A 120.0 . . ?
C9A C8A C12A 102(3) . . ?
C12A C8A C7 93.5(18) . . ?
C12A C8A H8A 120.0 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.2(6) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8A C9A H9AA 109.7 . . ?
C8A C9A H9AB 109.7 . . ?
H9AA C9A H9AB 108.2 . . ?
C10A C9A C8A 110(3) . . ?
C10A C9A H9AA 109.7 . . ?
C10A C9A H9AB 109.7 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C9 C10 C11 112.2(7) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9A C10A H10C 111.8 . . ?
C9A C10A H10D 111.8 . . ?
C9A C10A C11A 100(5) . . ?
H10C C10A H10D 109.5 . . ?
C11A C10A H10C 111.8 . . ?
C11A C10A H10D 111.8 . . ?
N2 C11 C10 110.8(11) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
N2 C11A C10A 111(3) . . ?
N2 C11A H11C 109.3 . . ?
N2 C11A H11D 109.3 . . ?
C10A C11A H11C 109.3 . . ?
C10A C11A H11D 109.3 . . ?
H11C C11A H11D 108.0 . . ?
S1 C12 H12A 108.4 . . ?
S1 C12 H12B 108.4 . . ?
C8 C12 S1 115.5(4) . . ?
C8 C12 H12A 108.4 . . ?
C8 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
S1A C12A H12C 109.8 . . ?
S1A C12A H12D 109.8 . . ?
C8A C12A S1A 110(2) . . ?
C8A C12A H12C 109.8 . . ?
C8A C12A H12D 109.8 . . ?
H12C C12A H12D 108.2 . . ?
F1 C13 S1 110.4(6) . . ?
F1 C13 F2 110.1(7) . . ?
F2 C13 S1 105.9(7) . . ?
F3 C13 S1 109.3(6) . . ?
F3 C13 F1 109.6(8) . . ?
F3 C13 F2 111.5(7) . . ?
S1A C13A F3A 123(3) . . ?
F1A C13A S1A 140(3) . . ?
F1A C13A F2A 89(3) . . ?
F1A C13A F3A 86(2) . . ?
F2A C13A S1A 117(2) . . ?
F2A C13A F3A 87(2) . . ?
C13' S1' C12' 95.2(4) . . ?
C13B S1'A C12B 114(3) . . ?
C7' N1' C5' 104.1(4) . . ?
C6' N2' C11' 125.4(4) . . ?
C7' N2' C6' 106.8(3) . . ?
C7' N2' C11' 127.7(5) . . ?
C2' C1' H1' 121.4 . . ?
C2' C1' C6' 117.2(5) . . ?
C6' C1' H1' 121.4 . . ?
C1' C2' H2' 119.2 . . ?
C1' C2' C3' 121.7(5) . . ?
C3' C2' H2' 119.2 . . ?
C2' C3' H3' 119.0 . . ?
C4' C3' C2' 121.9(5) . . ?
C4' C3' H3' 119.0 . . ?
C3' C4' H4' 121.0 . . ?
C3' C4' C5' 118.0(5) . . ?
C5' C4' H4' 121.0 . . ?
N1' C5' C4' 130.5(4) . . ?
N1' C5' C6' 110.0(4) . . ?
C4' C5' C6' 119.5(4) . . ?
N2' C6' C1' 132.8(4) . . ?
N2' C6' C5' 105.5(4) . . ?
C1' C6' C5' 121.7(5) . . ?
N1' C7' N2' 113.7(4) . . ?
N1' C7' C8' 124.9(5) . . ?
N1' C7' C8'A 126.0(14) . . ?
N2' C7' C8' 121.1(5) . . ?
N2' C7' C8'A 115.3(15) . . ?
C7' C8' H8' 98.4 . . ?
C9' C8' C7' 114.0(7) . . ?
C9' C8' H8' 98.4 . . ?
C9' C8' C12' 128.5(9) . . ?
C12' C8' C7' 111.1(6) . . ?
C12' C8' H8' 98.4 . . ?
C7' C8'A H8'A 111.0 . . ?
C9'A C8'A C7' 104(3) . . ?
C9'A C8'A H8'A 111.0 . . ?
C9'A C8'A C12B 121(5) . . ?
C12B C8'A C7' 97(3) . . ?
C12B C8'A H8'A 111.0 . . ?
C8' C9' H9'A 106.7 . . ?
C8' C9' H9'B 106.7 . . ?
C8' C9' C10' 122.6(8) . . ?
H9'A C9' H9'B 106.6 . . ?
C10' C9' H9'A 106.7 . . ?
C10' C9' H9'B 106.7 . . ?
C8'A C9'A H9'C 106.5 . . ?
C8'A C9'A H9'D 106.5 . . ?
C8'A C9'A C10B 123(4) . . ?
H9'C C9'A H9'D 106.5 . . ?
C10B C9'A H9'C 106.5 . . ?
C10B C9'A H9'D 106.5 . . ?
C9' C10' H10E 106.9 . . ?
C9' C10' H10F 106.9 . . ?
C9' C10' C11' 121.8(7) . . ?
H10E C10' H10F 106.7 . . ?
C11' C10' H10E 106.9 . . ?
C11' C10' H10F 106.9 . . ?
C9'A C10B H10G 112.7 . . ?
C9'A C10B H10H 112.7 . . ?
C9'A C10B C11' 95(3) . . ?
H10G C10B H10H 110.2 . . ?
C11' C10B H10G 112.7 . . ?
C11' C10B H10H 112.7 . . ?
N2' C11' C10' 112.3(6) . . ?
N2' C11' C10B 105.2(18) . . ?
N2' C11' H11E 109.1 . . ?
N2' C11' H11F 109.1 . . ?
N2' C11' H11G 110.7 . . ?
N2' C11' H11H 110.7 . . ?
C10' C11' H11E 109.1 . . ?
C10' C11' H11F 109.1 . . ?
C10B C11' H11G 110.7 . . ?
C10B C11' H11H 110.7 . . ?
H11E C11' H11F 107.9 . . ?
H11G C11' H11H 108.8 . . ?
S1' C12' H12E 109.9 . . ?
S1' C12' H12F 109.9 . . ?
C8' C12' S1' 108.8(7) . . ?
C8' C12' H12E 109.9 . . ?
C8' C12' H12F 109.9 . . ?
H12E C12' H12F 108.3 . . ?
S1'A C12B H12G 102.0 . . ?
S1'A C12B H12H 102.0 . . ?
C8'A C12B S1'A 140(4) . . ?
C8'A C12B H12G 102.0 . . ?
C8'A C12B H12H 102.0 . . ?
H12G C12B H12H 104.8 . . ?
F1' C13' S1' 111.8(9) . . ?
F2' C13' S1' 120.5(9) . . ?
F2' C13' F1' 102.0(10) . . ?
F2' C13' F3' 109.7(10) . . ?
F3' C13' S1' 110.7(9) . . ?
F3' C13' F1' 99.9(9) . . ?
F1'A C13B S1'A 89.8(14) . . ?
F1'A C13B F2'A 122(2) . . ?
F2'A C13B S1'A 102.9(17) . . ?
F3'A C13B S1'A 91.5(15) . . ?
F3'A C13B F1'A 120(2) . . ?
F3'A C13B F2'A 116(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C12 1.779(6) . ?
S1 C13 1.868(11) . ?
S1A C12A 1.790(18) . ?
S1A C13A 1.30(4) . ?
F1 C13 1.313(9) . ?
F1A C13A 1.30(3) . ?
F2 C13 1.328(7) . ?
F2A C13A 1.30(2) . ?
F3 C13 1.310(9) . ?
F3A C13A 1.321(19) . ?
N1 C5 1.390(6) . ?
N1 C7 1.296(6) . ?
N2 C6 1.364(6) . ?
N2 C7 1.366(6) . ?
N2 C11 1.464(9) . ?
N2 C11A 1.45(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.362(8) . ?
C1 C6 1.405(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.396(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(7) . ?
C5 C6 1.383(6) . ?
C7 C8 1.515(7) . ?
C7 C8A 1.57(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.549(10) . ?
C8 C12 1.540(9) . ?
C8A H8A 0.9800 . ?
C8A C9A 1.55(2) . ?
C8A C12A 1.55(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.498(10) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C9A C10A 1.53(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.543(17) . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C10A C11A 1.55(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
S1' C12' 1.792(10) . ?
S1' C13' 1.708(13) . ?
S1'A C12B 1.86(5) . ?
S1'A C13B 1.78(2) . ?
F1' C13' 1.370(11) . ?
F1'A C13B 1.366(15) . ?
F2' C13' 1.326(11) . ?
F2'A C13B 1.366(15) . ?
F3' C13' 1.336(9) . ?
F3'A C13B 1.363(15) . ?
N1' C5' 1.391(6) . ?
N1' C7' 1.317(6) . ?
N2' C6' 1.368(6) . ?
N2' C7' 1.361(6) . ?
N2' C11' 1.467(6) . ?
C1' H1' 0.9300 . ?
C1' C2' 1.362(9) . ?
C1' C6' 1.393(7) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.380(9) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.367(8) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.395(6) . ?
C5' C6' 1.401(6) . ?
C7' C8' 1.504(8) . ?
C7' C8'A 1.554(19) . ?
C8' H8' 0.9800 . ?
C8' C9' 1.463(10) . ?
C8' C12' 1.469(11) . ?
C8'A H8'A 0.9800 . ?
C8'A C9'A 1.51(2) . ?
C8'A C12B 1.54(2) . ?
C9' H9'A 0.9700 . ?
C9' H9'B 0.9700 . ?
C9' C10' 1.469(11) . ?
C9'A H9'C 0.9700 . ?
C9'A H9'D 0.9700 . ?
C9'A C10B 1.54(2) . ?
C10' H10E 0.9700 . ?
C10' H10F 0.9700 . ?
C10' C11' 1.478(10) . ?
C10B H10G 0.9700 . ?
C10B H10H 0.9700 . ?
C10B C11' 1.56(2) . ?
C11' H11E 0.9700 . ?
C11' H11F 0.9700 . ?
C11' H11G 0.9700 . ?
C11' H11H 0.9700 . ?
C12' H12E 0.9700 . ?
C12' H12F 0.9700 . ?
C12B H12G 0.9700 . ?
C12B H12H 0.9700 . ?