#------------------------------------------------------------------------------
#$Date: 2024-10-31 04:59:29 +0200 (Thu, 31 Oct 2024) $
#$Revision: 295688 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/26/2312677.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2312677
loop_
_publ_author_name
'Wang, Hui'
'Wu, Wen Xin'
'Jin, Wei Jun'
_publ_section_title
;
Cocrystals assembled from iodoperfluorobenzene and flexible NTPO via
halogen and π-hole bonds.
;
_journal_coeditor_code BS3005
_journal_issue 'Pt 2'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first 36
_journal_page_last 42
_journal_paper_doi 10.1107/S2053229622011822
_journal_volume 79
_journal_year 2023
_chemical_formula_iupac 'C6 F4 I2, C16 H13 N O S'
_chemical_formula_moiety 'C6 F4 I2, C16 H13 N O S'
_chemical_formula_sum 'C22 H13 F4 I2 N O S'
_chemical_formula_weight 669.19
_chemical_name_systematic
'1,4-Diiodotetrafluorobenzene--2-{[(naphthalen-2-yl)methyl]sulfanyl}pyridine 1-oxide (1/1)'
_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_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_cell_angle_alpha 71.495(4)
_cell_angle_beta 82.851(4)
_cell_angle_gamma 87.566(4)
_cell_formula_units_Z 2
_cell_length_a 6.9303(3)
_cell_length_b 12.6026(5)
_cell_length_c 13.1299(6)
_cell_measurement_reflns_used 5647
_cell_measurement_temperature 100.00(10)
_cell_measurement_theta_max 73.0730
_cell_measurement_theta_min 3.5680
_cell_volume 1079.01(8)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2019 (Sheldrick, 2015a)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015b)
;
_diffrn_ambient_temperature 100.00(10)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku OD SuperNova Dual source diffractometer with an AtlasS2 detector'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_wavelength 1.54184
_diffrn_reflns_av_R_equivalents 0.0341
_diffrn_reflns_av_unetI/netI 0.0350
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 6503
_diffrn_reflns_theta_full 66.594
_diffrn_reflns_theta_max 66.594
_diffrn_reflns_theta_min 3.574
_diffrn_source 'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu 24.249
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.58025
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2017)
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 2.060
_exptl_crystal_description plate
_exptl_crystal_F_000 636
_exptl_crystal_size_max 0.1
_exptl_crystal_size_mid 0.1
_exptl_crystal_size_min 0.05
_exptl_crystal_size_rad 0.0800
_refine_diff_density_max 1.544
_refine_diff_density_min -1.373
_refine_ls_extinction_coef 0.00114(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2019 (Sheldrick, 2015a)
;
_refine_ls_goodness_of_fit_ref 1.086
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 281
_refine_ls_number_reflns 3808
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.086
_refine_ls_R_factor_all 0.0350
_refine_ls_R_factor_gt 0.0343
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0661P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0936
_refine_ls_wR_factor_ref 0.0947
_reflns_number_gt 3699
_reflns_number_total 3808
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file bs3005sup1.cif
_cod_data_source_block 1
_cod_database_code 2312677
_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_min 0.195
_shelx_estimated_absorpt_t_max 0.377
_shelx_hkl_file
;
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0 0 8 354.304 15.662 0
0 0 9 1491.40 27.6374 0
0 0 9 1395.94 32.6213 0
0 0 10 10.5658 2.35158 0
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0 0 12 26.8349 3.42053 0
0 0 13 436.757 12.4339 0
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0 -1 7 35.4582 4.76155 0
0 -1 6 16.3473 3.0092 0
0 -1 5 11.5493 2.34072 0
0 -1 4 14.3516 2.39044 0
0 -1 3 719.139 15.2024 0
0 1 -2 13.1709 0.98348 0
0 -1 2 17.8666 2.0441 0
0 1 -1 207.699 4.23272 0
0 -1 1 208.939 5.66988 0
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0 1 1 6.93664 0.80267 0
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0 1 3 448.524 6.0734 0
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0 2 -14 22.0441 1.91263 0
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0 -2 8 723.725 24.0029 0
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0 2 1 167.567 4.34897 0
0 2 1 163.003 3.5769 0
0 2 2 277.467 7.03711 0
0 2 2 254.633 6.2337 0
0 2 3 2575.23 22.0881 0
0 2 3 2555.60 21.7941 0
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0 -3 4 3.78509 1.55609 0
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0 3 1 154.545 5.2264 0
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-7 3 1 70.8765 7.72535 0
-7 3 1 60.1266 3.98165 0
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7 -3 5 38.2088 2.97208 0
7 -3 6 9.39966 1.37365 0
7 -3 7 3.1993 0.73208 0
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7 -2 5 140.165 6.15599 0
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7 -2 6 301.417 8.65417 0
7 -2 7 328.502 8.46192 0
7 -2 8 82.7707 3.80279 0
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-7 1 0 11.7849 1.85161 0
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-7 1 -3 6.18839 1.34813 0
7 -1 4 7.80299 1.57663 0
-7 1 -4 8.1397 1.48043 0
7 -1 5 35.2756 3.23263 0
-7 1 -5 31.6021 2.88628 0
-7 1 -6 3.496 0.87656 0
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-7 0 -1 168.613 7.34988 0
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7 0 7 612.554 12.8176 0
-7 0 -7 598.082 11.897 0
7 0 8 4.83091 1.06809 0
-7 0 -8 6.14397 1.04359 0
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-7 -1 -3 1.85081 0.7228 0
7 1 4 78.1149 4.95236 0
-7 -1 -4 76.8294 5.15306 0
-7 -1 -5 1.57653 0.81231 0
7 1 5 1.47499 0.67337 0
7 1 6 90.8712 5.24277 0
-7 -1 -6 93.5424 5.41037 0
7 1 7 34.7408 3.10487 0
-7 -1 -7 33.316 3.01805 0
7 1 8 165.05 6.32177 0
-7 -1 -8 170.812 6.2425 0
7 1 9 17.5773 1.87491 0
-7 -1 -9 17.606 1.69316 0
7 1 10 21.5287 1.77339 0
-7 -2 6 245.798 7.11834 0
-7 -2 5 21.4549 2.49154 0
-7 -2 4 180.99 8.20885 0
-7 -2 4 157.283 4.90257 0
-7 -2 3 298.986 7.04718 0
-7 -2 3 306.568 8.85989 0
-7 -2 2 296.312 7.17237 0
-7 -2 2 265.539 8.41474 0
-7 -2 1 196.029 5.85107 0
-7 -2 1 182.171 7.26725 0
-7 -2 0 44.3398 3.64052 0
-7 -2 -1 489.11 12.6664 0
-7 -2 -2 44.5307 3.97068 0
-7 -2 -3 357.30 11.2923 0
-7 -2 -4 10.2641 1.92824 0
7 2 5 517.353 12.4242 0
-7 -2 -5 534.049 13.7714 0
7 2 6 43.7945 3.53757 0
-7 -2 -6 48.1613 4.02569 0
7 2 7 338.104 9.50926 0
-7 -2 -7 341.375 10.1706 0
7 2 8 161.507 6.19227 0
-7 -2 -8 171.441 6.63066 0
7 2 9 97.2615 4.37893 0
-7 -2 -9 107.734 4.65352 0
7 2 10 236.886 5.90049 0
-7 -2 -10 248.701 5.77071 0
-7 -3 5 135.77 5.52209 0
-7 -3 4 78.275 4.91821 0
-7 -3 4 72.9308 3.23846 0
-7 -3 3 18.4366 2.60739 0
-7 -3 3 16.2787 1.59341 0
-7 -3 3 18.0769 1.99301 0
-7 -3 2 158.199 5.19517 0
-7 -3 2 156.204 6.20036 0
-7 -3 1 40.6433 2.69279 0
-7 -3 1 37.9767 3.21668 0
-7 -3 0 279.037 7.0486 0
-7 -3 0 253.728 8.50198 0
-7 -3 -1 18.3332 2.4107 0
-7 -3 -2 427.345 11.9926 0
-7 -3 -3 1.2979 0.71384 0
-7 -3 -4 223.731 9.07055 0
-7 -3 -5 158.767 7.56564 0
7 3 6 233.791 7.88576 0
-7 -3 -6 255.309 9.38134 0
7 3 7 36.9824 3.00341 0
-7 -3 -7 39.8068 3.52019 0
7 3 8 44.7388 3.10811 0
-7 -3 -8 46.8906 3.59624 0
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7 4 8 123.014 4.77874 0
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7 4 9 23.4881 1.89327 0
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7 5 1 46.8595 2.98061 0
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-7 -6 2 54.9323 2.70614 0
-7 -6 1 63.7178 3.1149 0
-7 -6 0 4.77234 0.98109 0
7 6 1 2.29323 0.59584 0
7 6 2 99.6954 4.24419 0
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7 6 3 30.9498 2.31818 0
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-7 -6 -7 0.39337 0.23602 0
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-7 -6 -10 5.8892 0.92175 0
-7 -7 2 172.237 4.2296 0
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-7 -7 0 138.412 4.42625 0
7 7 1 290.946 6.62538 0
7 7 2 6.28836 0.96405 0
7 7 3 526.094 9.12316 0
7 7 4 8.53362 1.11973 0
-7 -7 -4 8.99236 1.32197 0
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7 8 2 1.56342 0.40498 0
7 8 3 2.8394 0.57453 0
7 8 4 5.87228 0.84298 0
7 8 5 15.4397 1.34486 0
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-7 -9 -2 31.0448 1.71245 0
7 9 3 210.267 4.4698 0
7 9 4 36.1664 1.8568 0
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-8 3 0 52.6219 2.73415 0
-8 3 -1 10.9999 1.21182 0
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-8 2 2 4.5204 0.83075 0
-8 2 1 442.515 8.48873 0
-8 2 0 14.042 1.51703 0
-8 2 -1 259.586 6.3418 0
-8 2 -2 12.9183 1.35158 0
-8 2 -3 134.319 4.13203 0
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-8 1 1 1.12234 0.38359 0
-8 1 0 23.7708 2.01796 0
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-8 0 2 124.694 4.54247 0
-8 0 1 238.944 6.52971 0
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-8 0 -1 158.899 5.36211 0
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-8 0 -6 325.678 5.98811 0
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-8 -1 2 11.3583 1.34445 0
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-8 -1 -5 47.6405 2.75848 0
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-8 -2 2 282.894 7.92817 0
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-8 -3 1 95.5501 3.57726 0
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-8 -4 -6 1.18862 0.43598 0
-8 -4 -7 109.548 3.67652 0
-8 -5 -3 24.1875 1.7415 0
-8 -5 -4 432.378 7.4563 0
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-8 -5 -6 116.474 3.78043 0
0 0 0 0. 0.
;
_shelx_hkl_checksum 61651
_shelx_res_file
;
TITL 1.res in P-1
1.res
created by SHELXL-2018/3 at 20:53:28 on 23-Dec-2022
CELL 1.54184 6.9303 12.6026 13.1299 71.495 82.851 87.566
ZERR 2 0.0003 0.0005 0.0006 0.004 0.004 0.004
LATT 1
SFAC C H F I N O S
UNIT 44 26 8 4 2 2 2
L.S. 8
ACTA
BOND $H
FMAP 2
PLAN 1
SHEL 999 0.84
MORE -1
CONF
SIZE 0.05 0.1 0.1
TEMP -173
WGHT 0.066100
EXTI 0.001139
FVAR 0.31492
I1 4 0.792246 0.520963 0.772018 11.00000 0.01637 0.01961 =
0.01874 -0.00488 -0.00222 0.00049
I2 4 0.802144 1.075285 0.773511 11.00000 0.01732 0.01868 =
0.01657 -0.00338 -0.00186 0.00037
S1 7 0.756155 0.371176 0.530456 11.00000 0.01613 0.02707 =
0.01025 -0.00372 0.00003 -0.00062
F1 3 0.757246 0.628882 0.968515 11.00000 0.03659 0.02254 =
0.01201 0.00251 -0.00048 -0.00216
F2 3 0.762872 0.840371 0.967894 11.00000 0.02710 0.02640 =
0.01114 -0.00497 0.00032 -0.00013
F3 3 0.845596 0.965256 0.585595 11.00000 0.03260 0.02420 =
0.00907 0.00183 -0.00088 0.00023
F4 3 0.846044 0.754191 0.585430 11.00000 0.03010 0.03079 =
0.01145 -0.00795 0.00014 -0.00087
O1 6 0.743561 0.312188 0.747515 11.00000 0.01358 0.02017 =
0.01476 -0.00332 -0.00461 0.00187
N1 5 0.564035 0.311141 0.722330 11.00000 0.01522 0.01856 =
0.01230 -0.00390 0.00021 0.00133
C1 1 0.411525 0.288648 0.800813 11.00000 0.01914 0.02713 =
0.01274 -0.00314 -0.00197 0.00186
AFIX 43
H1 2 0.432518 0.277221 0.873673 11.00000 -1.20000
AFIX 0
C2 1 0.225721 0.282164 0.775919 11.00000 0.01730 0.02873 =
0.01946 -0.00046 0.00226 0.00042
AFIX 43
H2 2 0.118240 0.266720 0.830856 11.00000 -1.20000
AFIX 0
C3 1 0.199060 0.298651 0.669070 11.00000 0.01709 0.02765 =
0.02634 -0.00433 -0.00489 0.00094
AFIX 43
H3 2 0.072534 0.292280 0.650896 11.00000 -1.20000
AFIX 0
C4 1 0.354247 0.324197 0.588906 11.00000 0.01933 0.02431 =
0.01915 -0.00491 -0.00579 0.00006
AFIX 43
H4 2 0.334957 0.335891 0.515755 11.00000 -1.20000
AFIX 0
C5 1 0.540169 0.332723 0.616271 11.00000 0.02064 0.01939 =
0.00829 -0.00086 0.00093 -0.00167
C6 1 0.674084 0.403851 0.398108 11.00000 0.02404 0.02631 =
0.00925 0.00040 0.00037 -0.00123
AFIX 23
H6A 2 0.538940 0.432272 0.402571 11.00000 -1.20000
H6B 2 0.755586 0.465276 0.347165 11.00000 -1.20000
AFIX 0
C7 1 0.678790 0.308267 0.350929 11.00000 0.01074 0.02902 =
0.01586 -0.00651 0.00009 0.00371
C8 1 0.703250 0.333834 0.240233 11.00000 0.01697 0.02672 =
0.01243 -0.00150 -0.00119 -0.00013
AFIX 43
H8 2 0.717933 0.409959 0.196803 11.00000 -1.20000
AFIX 0
C9 1 0.707234 0.250785 0.189164 11.00000 0.01382 0.02926 =
0.01259 -0.00208 -0.00179 0.00018
C10 1 0.734522 0.277238 0.075191 11.00000 0.01592 0.03541 =
0.01305 -0.00313 -0.00129 0.00200
AFIX 43
H10 2 0.744941 0.353242 0.030931 11.00000 -1.20000
AFIX 0
C11 1 0.746043 0.193738 0.028139 11.00000 0.01925 0.05026 =
0.01402 -0.01329 -0.00218 0.00479
AFIX 43
H11 2 0.768778 0.212136 -0.048326 11.00000 -1.20000
AFIX 0
C12 1 0.724154 0.080385 0.093202 11.00000 0.01770 0.04296 =
0.02433 -0.01877 -0.00523 0.00483
AFIX 43
H12 2 0.729514 0.023243 0.060029 11.00000 -1.20000
AFIX 0
C13 1 0.695400 0.052627 0.203278 11.00000 0.01844 0.02888 =
0.02229 -0.00587 -0.00287 -0.00318
AFIX 43
H13 2 0.679585 -0.023726 0.245824 11.00000 -1.20000
AFIX 0
C14 1 0.688806 0.135717 0.254877 11.00000 0.01248 0.02956 =
0.01817 -0.00424 -0.00227 0.00045
C15 1 0.663335 0.110857 0.368457 11.00000 0.01425 0.02539 =
0.01782 -0.00196 -0.00140 0.00367
AFIX 43
H15 2 0.649819 0.035091 0.413066 11.00000 -1.20000
AFIX 0
C16 1 0.657683 0.194308 0.415928 11.00000 0.02116 0.02617 =
0.01014 -0.00064 0.00189 -0.00090
AFIX 43
H16 2 0.639583 0.175524 0.492495 11.00000 -1.20000
AFIX 0
C17 1 0.800482 0.684623 0.777053 11.00000 0.01659 0.01861 =
0.01553 -0.00052 -0.00179 0.00064
C18 1 0.780036 0.711413 0.872536 11.00000 0.01834 0.02228 =
0.00965 0.00204 0.00070 -0.00267
C19 1 0.783032 0.820340 0.872401 11.00000 0.01405 0.02412 =
0.01084 -0.00283 -0.00081 0.00225
C20 1 0.803999 0.909516 0.776693 11.00000 0.01820 0.01728 =
0.01269 -0.00009 0.00158 -0.00131
C21 1 0.826398 0.883408 0.680686 11.00000 0.01717 0.02368 =
0.00764 0.00059 0.00091 -0.00101
C22 1 0.823916 0.774500 0.680914 11.00000 0.01520 0.02297 =
0.01356 -0.00296 -0.00266 0.00302
HKLF 4
REM 1.res in P-1
REM wR2 = 0.0947, GooF = S = 1.086, Restrained GooF = 1.086 for all data
REM R1 = 0.0343 for 3699 Fo > 4sig(Fo) and 0.0350 for all 3808 data
REM 281 parameters refined using 0 restraints
END
WGHT 0.0661 0.0000
REM Highest difference peak 1.544, deepest hole -1.373, 1-sigma level 0.163
Q1 1 0.8689 1.0571 0.7168 11.00000 0.05 1.54
;
_shelx_res_checksum 73698
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.79225(3) 0.52096(2) 0.77202(2) 0.01851(12) Uani d 1 . .
I I2 0.80214(3) 1.07529(2) 0.77351(2) 0.01806(13) Uani d 1 . .
S S1 0.75615(13) 0.37118(8) 0.53046(7) 0.0185(2) Uani d 1 . .
F F1 0.7572(4) 0.6289(2) 0.9685(2) 0.0257(5) Uani d 1 . .
F F2 0.7629(4) 0.8404(2) 0.96789(19) 0.0220(5) Uani d 1 . .
F F3 0.8456(4) 0.9653(2) 0.58559(19) 0.0238(5) Uani d 1 . .
F F4 0.8460(4) 0.7542(2) 0.58543(19) 0.0240(5) Uani d 1 . .
O O1 0.7436(4) 0.3122(2) 0.7475(2) 0.0165(5) Uani d 1 . .
N N1 0.5640(5) 0.3111(3) 0.7223(3) 0.0158(6) Uani d 1 . .
C C1 0.4115(6) 0.2886(3) 0.8008(3) 0.0205(8) Uani d 1 . .
H H1 0.432518 0.277221 0.873673 0.025 Uiso calc 1 . .
C C2 0.2257(6) 0.2822(4) 0.7759(4) 0.0239(9) Uani d 1 . .
H H2 0.118240 0.266720 0.830856 0.029 Uiso calc 1 . .
C C3 0.1991(6) 0.2987(3) 0.6691(4) 0.0245(8) Uani d 1 . .
H H3 0.072534 0.292280 0.650896 0.029 Uiso calc 1 . .
C C4 0.3542(6) 0.3242(3) 0.5889(3) 0.0211(8) Uani d 1 . .
H H4 0.334957 0.335891 0.515755 0.025 Uiso calc 1 . .
C C5 0.5402(6) 0.3327(3) 0.6163(3) 0.0171(7) Uani d 1 . .
C C6 0.6741(6) 0.4039(3) 0.3981(3) 0.0215(8) Uani d 1 . .
H H6A 0.538940 0.432272 0.402571 0.026 Uiso calc 1 . .
H H6B 0.755586 0.465276 0.347165 0.026 Uiso calc 1 . .
C C7 0.6788(6) 0.3083(4) 0.3509(3) 0.0189(8) Uani d 1 . .
C C8 0.7032(6) 0.3338(4) 0.2402(3) 0.0199(8) Uani d 1 . .
H H8 0.717933 0.409959 0.196803 0.024 Uiso calc 1 . .
C C9 0.7072(6) 0.2508(4) 0.1892(3) 0.0196(8) Uani d 1 . .
C C10 0.7345(6) 0.2772(4) 0.0752(3) 0.0226(9) Uani d 1 . .
H H10 0.744941 0.353242 0.030931 0.027 Uiso calc 1 . .
C C11 0.7460(7) 0.1937(4) 0.0281(4) 0.0272(10) Uani d 1 . .
H H11 0.768778 0.212136 -0.048326 0.033 Uiso calc 1 . .
C C12 0.7242(6) 0.0804(4) 0.0932(4) 0.0263(9) Uani d 1 . .
H H12 0.729514 0.023243 0.060029 0.032 Uiso calc 1 . .
C C13 0.6954(6) 0.0526(4) 0.2033(4) 0.0236(9) Uani d 1 . .
H H13 0.679585 -0.023726 0.245824 0.028 Uiso calc 1 . .
C C14 0.6888(6) 0.1357(4) 0.2549(3) 0.0208(8) Uani d 1 . .
C C15 0.6633(6) 0.1109(4) 0.3685(3) 0.0205(8) Uani d 1 . .
H H15 0.649819 0.035091 0.413066 0.025 Uiso calc 1 . .
C C16 0.6577(6) 0.1943(4) 0.4159(3) 0.0207(8) Uani d 1 . .
H H16 0.639583 0.175524 0.492495 0.025 Uiso calc 1 . .
C C17 0.8005(6) 0.6846(3) 0.7771(3) 0.0181(8) Uani d 1 . .
C C18 0.7800(6) 0.7114(3) 0.8725(3) 0.0186(8) Uani d 1 . .
C C19 0.7830(6) 0.8203(3) 0.8724(3) 0.0171(8) Uani d 1 . .
C C20 0.8040(6) 0.9095(3) 0.7767(3) 0.0174(8) Uani d 1 . .
C C21 0.8264(6) 0.8834(3) 0.6807(3) 0.0177(8) Uani d 1 . .
C C22 0.8239(6) 0.7745(3) 0.6809(3) 0.0179(8) Uani d 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
I1 0.01637(17) 0.01961(17) 0.01874(17) 0.00049(10) -0.00222(11) -0.00488(11)
I2 0.01732(17) 0.01868(17) 0.01657(17) 0.00037(11) -0.00186(11) -0.00338(11)
S1 0.0161(4) 0.0271(5) 0.0102(4) -0.0006(3) 0.0000(3) -0.0037(3)
F1 0.0366(14) 0.0225(11) 0.0120(12) -0.0022(10) -0.0005(10) 0.0025(9)
F2 0.0271(12) 0.0264(12) 0.0111(11) -0.0001(10) 0.0003(9) -0.0050(9)
F3 0.0326(13) 0.0242(11) 0.0091(11) 0.0002(10) -0.0009(9) 0.0018(9)
F4 0.0301(13) 0.0308(12) 0.0115(11) -0.0009(10) 0.0001(10) -0.0079(9)
O1 0.0136(13) 0.0202(12) 0.0148(13) 0.0019(10) -0.0046(11) -0.0033(10)
N1 0.0152(16) 0.0186(15) 0.0123(15) 0.0013(12) 0.0002(12) -0.0039(12)
C1 0.019(2) 0.027(2) 0.0127(18) 0.0019(16) -0.0020(15) -0.0031(15)
C2 0.017(2) 0.029(2) 0.019(2) 0.0004(17) 0.0023(16) -0.0005(16)
C3 0.0171(19) 0.028(2) 0.026(2) 0.0009(16) -0.0049(16) -0.0043(17)
C4 0.019(2) 0.024(2) 0.019(2) 0.0001(15) -0.0058(16) -0.0049(16)
C5 0.0206(19) 0.0194(17) 0.0083(17) -0.0017(14) 0.0009(14) -0.0009(14)
C6 0.024(2) 0.0263(19) 0.0093(17) -0.0012(16) 0.0004(15) 0.0004(15)
C7 0.0107(17) 0.029(2) 0.0159(19) 0.0037(15) 0.0001(14) -0.0065(16)
C8 0.0170(19) 0.027(2) 0.0124(18) -0.0001(15) -0.0012(14) -0.0015(16)
C9 0.0138(18) 0.029(2) 0.0126(19) 0.0002(16) -0.0018(15) -0.0021(16)
C10 0.0159(19) 0.035(2) 0.0131(19) 0.0020(16) -0.0013(15) -0.0031(17)
C11 0.019(2) 0.050(3) 0.014(2) 0.0048(19) -0.0022(16) -0.0133(19)
C12 0.018(2) 0.043(2) 0.024(2) 0.0048(18) -0.0052(17) -0.0188(19)
C13 0.018(2) 0.029(2) 0.022(2) -0.0032(16) -0.0029(16) -0.0059(17)
C14 0.0125(19) 0.030(2) 0.018(2) 0.0005(15) -0.0023(15) -0.0042(17)
C15 0.0143(19) 0.0254(19) 0.018(2) 0.0037(15) -0.0014(15) -0.0020(16)
C16 0.021(2) 0.026(2) 0.0101(18) -0.0009(16) 0.0019(15) -0.0006(16)
C17 0.0166(19) 0.0186(18) 0.016(2) 0.0006(15) -0.0018(15) -0.0005(15)
C18 0.0183(19) 0.0223(19) 0.0097(18) -0.0027(15) 0.0007(14) 0.0020(15)
C19 0.0140(18) 0.0241(19) 0.0108(18) 0.0022(15) -0.0008(14) -0.0028(15)
C20 0.0182(19) 0.0173(18) 0.0127(19) -0.0013(15) 0.0016(14) -0.0001(15)
C21 0.0172(19) 0.0237(19) 0.0076(18) -0.0010(15) 0.0009(14) 0.0006(15)
C22 0.0152(19) 0.0230(19) 0.0136(19) 0.0030(15) -0.0027(14) -0.0030(15)
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'
I I -0.3257 6.8362 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 S1 C6 . . 102.10(19) ?
O1 N1 C1 . . 120.2(3) ?
O1 N1 C5 . . 118.0(3) ?
C1 N1 C5 . . 121.8(3) ?
N1 C1 C2 . . 120.5(4) ?
N1 C1 H1 . . 119.7 ?
C2 C1 H1 . . 119.7 ?
C1 C2 C3 . . 118.6(4) ?
C1 C2 H2 . . 120.7 ?
C3 C2 H2 . . 120.7 ?
C4 C3 C2 . . 120.7(4) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C3 C4 C5 . . 119.4(4) ?
C3 C4 H4 . . 120.3 ?
C5 C4 H4 . . 120.3 ?
N1 C5 C4 . . 118.8(4) ?
N1 C5 S1 . . 112.8(3) ?
C4 C5 S1 . . 128.4(3) ?
C7 C6 S1 . . 116.2(3) ?
C7 C6 H6A . . 108.2 ?
S1 C6 H6A . . 108.2 ?
C7 C6 H6B . . 108.2 ?
S1 C6 H6B . . 108.2 ?
H6A C6 H6B . . 107.4 ?
C8 C7 C16 . . 118.9(4) ?
C8 C7 C6 . . 118.1(4) ?
C16 C7 C6 . . 122.9(4) ?
C7 C8 C9 . . 122.1(4) ?
C7 C8 H8 . . 118.9 ?
C9 C8 H8 . . 118.9 ?
C8 C9 C10 . . 122.0(4) ?
C8 C9 C14 . . 118.9(4) ?
C10 C9 C14 . . 119.1(4) ?
C11 C10 C9 . . 120.5(4) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
C10 C11 C12 . . 120.2(4) ?
C10 C11 H11 . . 119.9 ?
C12 C11 H11 . . 119.9 ?
C13 C12 C11 . . 120.5(4) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
C12 C13 C14 . . 121.0(4) ?
C12 C13 H13 . . 119.5 ?
C14 C13 H13 . . 119.5 ?
C15 C14 C13 . . 123.0(4) ?
C15 C14 C9 . . 118.3(4) ?
C13 C14 C9 . . 118.7(4) ?
C16 C15 C14 . . 121.4(4) ?
C16 C15 H15 . . 119.3 ?
C14 C15 H15 . . 119.3 ?
C15 C16 C7 . . 120.4(4) ?
C15 C16 H16 . . 119.8 ?
C7 C16 H16 . . 119.8 ?
C18 C17 C22 . . 116.4(4) ?
C18 C17 I1 . . 123.4(3) ?
C22 C17 I1 . . 120.2(3) ?
F1 C18 C19 . . 118.7(4) ?
F1 C18 C17 . . 119.7(4) ?
C19 C18 C17 . . 121.6(4) ?
F2 C19 C18 . . 118.6(4) ?
F2 C19 C20 . . 119.7(4) ?
C18 C19 C20 . . 121.8(4) ?
C21 C20 C19 . . 117.0(4) ?
C21 C20 I2 . . 120.2(3) ?
C19 C20 I2 . . 122.8(3) ?
F3 C21 C22 . . 118.7(4) ?
F3 C21 C20 . . 120.1(4) ?
C22 C21 C20 . . 121.2(4) ?
F4 C22 C21 . . 118.6(4) ?
F4 C22 C17 . . 119.4(4) ?
C21 C22 C17 . . 122.0(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 C17 . 2.088(4) ?
I2 C20 . 2.076(4) ?
S1 C5 . 1.744(4) ?
S1 C6 . 1.812(4) ?
F1 C18 . 1.352(5) ?
F2 C19 . 1.345(5) ?
F3 C21 . 1.339(5) ?
F4 C22 . 1.347(5) ?
O1 N1 . 1.328(4) ?
N1 C1 . 1.352(5) ?
N1 C5 . 1.361(5) ?
C1 C2 . 1.379(6) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.386(6) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.379(6) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.397(6) ?
C4 H4 . 0.9500 ?
C6 C7 . 1.517(6) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.375(6) ?
C7 C16 . 1.422(6) ?
C8 C9 . 1.409(6) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.416(6) ?
C9 C14 . 1.434(7) ?
C10 C11 . 1.374(7) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.416(7) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.365(6) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.413(6) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.413(6) ?
C15 C16 . 1.379(6) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 C18 . 1.388(6) ?
C17 C22 . 1.400(6) ?
C18 C19 . 1.373(7) ?
C19 C20 . 1.391(6) ?
C20 C21 . 1.390(6) ?
C21 C22 . 1.372(6) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 N1 C1 C2 . . . . -176.9(4) ?
C5 N1 C1 C2 . . . . 2.8(6) ?
N1 C1 C2 C3 . . . . 0.3(6) ?
C1 C2 C3 C4 . . . . -1.9(6) ?
C2 C3 C4 C5 . . . . 0.4(6) ?
O1 N1 C5 C4 . . . . 175.5(3) ?
C1 N1 C5 C4 . . . . -4.2(6) ?
O1 N1 C5 S1 . . . . -5.6(4) ?
C1 N1 C5 S1 . . . . 174.7(3) ?
C3 C4 C5 N1 . . . . 2.6(6) ?
C3 C4 C5 S1 . . . . -176.1(3) ?
C6 S1 C5 N1 . . . . -175.9(3) ?
C6 S1 C5 C4 . . . . 2.9(4) ?
C5 S1 C6 C7 . . . . -91.4(3) ?
S1 C6 C7 C8 . . . . -151.7(3) ?
S1 C6 C7 C16 . . . . 28.7(5) ?
C16 C7 C8 C9 . . . . 0.3(6) ?
C6 C7 C8 C9 . . . . -179.3(4) ?
C7 C8 C9 C10 . . . . -179.3(4) ?
C7 C8 C9 C14 . . . . -1.2(7) ?
C8 C9 C10 C11 . . . . 177.2(4) ?
C14 C9 C10 C11 . . . . -0.9(7) ?
C9 C10 C11 C12 . . . . 2.1(7) ?
C10 C11 C12 C13 . . . . -1.3(7) ?
C11 C12 C13 C14 . . . . -0.7(7) ?
C12 C13 C14 C15 . . . . -178.7(4) ?
C12 C13 C14 C9 . . . . 1.8(7) ?
C8 C9 C14 C15 . . . . 1.3(7) ?
C10 C9 C14 C15 . . . . 179.5(3) ?
C8 C9 C14 C13 . . . . -179.2(3) ?
C10 C9 C14 C13 . . . . -1.0(7) ?
C13 C14 C15 C16 . . . . 180.0(4) ?
C9 C14 C15 C16 . . . . -0.5(7) ?
C14 C15 C16 C7 . . . . -0.4(7) ?
C8 C7 C16 C15 . . . . 0.5(6) ?
C6 C7 C16 C15 . . . . -179.9(4) ?
C22 C17 C18 F1 . . . . -179.9(3) ?
I1 C17 C18 F1 . . . . 1.4(6) ?
C22 C17 C18 C19 . . . . -0.1(6) ?
I1 C17 C18 C19 . . . . -178.9(3) ?
F1 C18 C19 F2 . . . . -0.1(6) ?
C17 C18 C19 F2 . . . . -179.8(3) ?
F1 C18 C19 C20 . . . . -179.3(4) ?
C17 C18 C19 C20 . . . . 0.9(7) ?
F2 C19 C20 C21 . . . . 179.3(3) ?
C18 C19 C20 C21 . . . . -1.4(6) ?
F2 C19 C20 I2 . . . . -0.8(5) ?
C18 C19 C20 I2 . . . . 178.4(3) ?
C19 C20 C21 F3 . . . . 179.4(3) ?
I2 C20 C21 F3 . . . . -0.4(5) ?
C19 C20 C21 C22 . . . . 1.3(6) ?
I2 C20 C21 C22 . . . . -178.6(3) ?
F3 C21 C22 F4 . . . . 1.7(6) ?
C20 C21 C22 F4 . . . . 179.9(3) ?
F3 C21 C22 C17 . . . . -178.7(3) ?
C20 C21 C22 C17 . . . . -0.5(7) ?
C18 C17 C22 F4 . . . . 179.5(4) ?
I1 C17 C22 F4 . . . . -1.7(5) ?
C18 C17 C22 C21 . . . . -0.1(6) ?
I1 C17 C22 C21 . . . . 178.7(3) ?
_cod_database_fobs_code 2312677