#------------------------------------------------------------------------------
#$Date: 2024-07-09 05:03:07 +0300 (Tue, 09 Jul 2024) $
#$Revision: 293325 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/25/2312541.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_2312541
loop_
_publ_author_name
'Ma, Yu Heng'
'Yang, Kang'
'Qian, Yan Ling'
'Hong, Wei Pu'
'Zhang, Kai Yue'
'Tao, Zhen Wei'
'Meng, Hui'
'Ma, Wen Jing'
_publ_section_title
;
Supramolecular interactions in cocrystals of benzoic acid derivatives
with selective COX-2 inhibitor etoricoxib.
;
_journal_coeditor_code YP3237
_journal_issue 8
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi 10.1107/S2053229624006193
_journal_volume 80
_journal_year 2024
_chemical_formula_iupac 'C18 H15 Cl N2 O2 S, C7 H6 O2'
_chemical_formula_moiety 'C18 H15 Cl N2 O2 S, C7 H6 O2'
_chemical_formula_sum 'C25 H21 Cl N2 O4 S'
_chemical_formula_weight 480.95
_chemical_name_common
;
Etoricoxib--benzoic acid (1/1)
;
_chemical_name_systematic
;
5-Chloro-2-(6-methylpyridin-3-yl)-3-[4-(methylsulfonyl)phenyl]pyridine--\
benzoic acid
;
_space_group_crystal_system orthorhombic
_space_group_IT_number 61
_space_group_name_Hall '-P 2ac 2ab'
_space_group_name_H-M_alt 'P b c a'
_atom_sites_solution_hydrogens geom
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_formula_units_Z 8
_cell_length_a 10.7920(2)
_cell_length_b 18.7130(4)
_cell_length_c 23.2990(5)
_cell_measurement_reflns_used 25
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 13
_cell_measurement_theta_min 9
_cell_volume 4705.25(17)
_computing_cell_refinement
;
CAD-4 Software (Enraf--Nonius, 1985)
;
_computing_data_collection
;
CAD-4 Software (Enraf--Nonius, 1985)
;
_computing_data_reduction
;
XCAD4 (Harms & Wocadlo, 1995)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009) and
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009) and
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
olex2.refine (Bourhis et al., 2015) and
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type 'Nonius CAD4'
_diffrn_measurement_method \w/2\q
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0943
_diffrn_reflns_av_unetI/netI 0.1156
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_h_min 0
_diffrn_reflns_limit_k_max 22
_diffrn_reflns_limit_k_min 0
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 7760
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 25.390
_diffrn_reflns_theta_min 2.573
_diffrn_standards_decay_% 1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time 2h
_diffrn_standards_number 3
_exptl_absorpt_coefficient_mu 0.286
_exptl_absorpt_correction_T_max 0.9720
_exptl_absorpt_correction_T_min 0.9192
_exptl_absorpt_correction_type psi-scan
_exptl_absorpt_process_details
;
(North et al., 1968)
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.358
_exptl_crystal_description needle
_exptl_crystal_F_000 2000
_exptl_crystal_size_max 0.46
_exptl_crystal_size_mid 0.1
_exptl_crystal_size_min 0.08
_refine_diff_density_max 0.293
_refine_diff_density_min -0.567
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.015
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 301
_refine_ls_number_reflns 4277
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.015
_refine_ls_R_factor_all 0.1591
_refine_ls_R_factor_gt 0.0681
_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^)+(0.0778P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1426
_refine_ls_wR_factor_ref 0.1922
_reflns_number_gt 2113
_reflns_number_total 4277
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file yp3237sup1.cif
_cod_data_source_block etr-bz
_cod_database_code 2312541
_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 0.880
_shelx_estimated_absorpt_t_max 0.978
_shelx_hkl_file
;
0 0 -18 1.09 9.43
0 0 -17 -17.28 11.87
0 0 -16 71.88 15.23
0 0 -15 -16.08 16.47
0 0 -14 52.95 18.96
0 0 -6 6659.99 111.14
0 0 -4 8825.70 101.82
0 0 4 8741.99 102.52
0 0 6 6261.16 108.46
0 0 14 14.59 19.18
0 0 15 -37.72 16.20
0 0 16 93.64 14.99
0 0 17 -60.31 13.18
0 0 18 -1.45 9.72
0 0 19 -85.40 12.19
0 0 20 619.01 18.82
0 0 22 -2.81 10.07
0 0 23 -48.21 12.64
0 0 24 210.07 14.96
0 0 25 -109.17 15.40
0 0 26 -7.65 10.58
0 0 27 -5.59 11.13
0 0 28 -12.44 10.49
0 1 28 3.28 7.84
0 1 27 8.09 7.79
0 1 26 7.66 6.32
0 1 25 3.91 6.72
0 1 24 3.16 6.20
0 1 23 -9.46 6.88
0 1 22 4.69 5.47
0 1 21 -3.98 5.25
0 1 20 2.08 5.83
0 1 19 -7.01 5.31
0 1 18 5.10 4.49
0 1 17 0.34 4.87
0 1 16 -7.59 4.52
0 1 15 2.06 3.23
0 1 14 2.44 3.22
0 1 13 3.50 2.83
0 1 12 1.83 3.33
0 1 11 1.25 2.70
0 1 10 1.32 2.49
0 1 9 0.51 2.28
0 1 8 1.19 2.20
0 1 7 0.00 1.66
0 1 6 1.79 1.68
0 1 5 2.34 2.23
0 1 4 3.87 3.44
0 1 3 -11.63 1.79
0 1 2 -0.55 0.79
0 1 1 5.58 0.70
0 1 -1 5.55 0.71
0 1 -2 -1.23 0.77
0 1 -3 -1.00 1.14
0 1 -4 3.64 3.41
0 1 -5 -1.50 2.48
0 1 -6 1.79 1.68
0 1 -7 0.13 1.75
0 1 -8 2.24 2.30
0 1 -9 0.84 2.40
0 1 -10 4.33 2.30
0 1 -11 0.42 3.03
0 1 -12 6.63 3.11
0 1 -13 2.75 3.23
0 1 -14 0.00 3.52
0 1 -15 5.28 3.45
0 1 -16 -0.95 4.35
0 1 -17 8.50 4.01
0 1 -18 1.46 4.52
0 2 -18 261.17 11.54
0 2 -17 71.03 7.35
0 2 -16 367.07 12.39
0 2 -15 -7.43 4.36
0 2 -14 172.12 7.86
0 2 -13 257.84 9.41
0 2 -12 208.26 8.22
0 2 -11 324.53 9.77
0 2 -10 1546.98 19.13
0 2 -9 -6.07 2.89
0 2 -6 177.22 5.30
0 2 -5 165.50 5.18
0 2 -4 6.58 1.32
0 2 -3 280.91 5.33
0 2 -2 197.32 4.12
0 2 0 2410.12 42.13
0 2 2 198.73 3.96
0 2 4 7.18 1.36
0 2 5 162.83 5.09
0 2 6 192.84 5.82
0 2 9 -8.15 2.98
0 2 10 1445.98 18.51
0 2 11 313.16 9.42
0 2 12 186.22 8.13
0 2 13 256.39 9.33
0 2 14 138.62 8.06
0 2 15 -7.72 4.35
0 2 16 351.80 12.47
0 2 17 66.93 7.59
0 2 18 251.31 11.35
0 2 19 0.39 10.75
0 2 20 321.56 14.95
0 2 22 -77.01 10.60
0 2 23 42.58 11.12
0 2 24 -67.36 12.92
0 2 25 -23.56 9.72
0 2 26 -7.11 8.58
0 2 27 -34.37 10.25
0 3 27 3.78 7.71
0 3 26 1.79 7.09
0 3 25 -2.83 6.81
0 3 24 3.75 6.45
0 3 23 -0.51 6.42
0 3 22 1.91 5.57
0 3 21 9.00 5.76
0 3 20 1.69 5.65
0 3 19 12.32 5.26
0 3 18 3.73 4.80
0 3 17 -6.28 4.98
0 3 16 -4.23 4.21
0 3 15 -9.69 6.10
0 3 14 -2.53 3.68
0 3 13 -0.52 3.03
0 3 12 -21.54 7.93
0 3 11 -0.44 2.88
0 3 10 3.60 2.77
0 3 9 -0.18 2.84
0 3 8 -0.49 2.17
0 3 7 2.05 2.22
0 3 6 1.55 1.59
0 3 5 -0.23 1.87
0 3 4 0.50 1.93
0 3 3 -14.35 2.80
0 3 2 1.23 1.24
0 3 1 2.31 1.01
0 3 -1 0.77 0.97
0 3 -2 -1.38 1.26
0 3 -4 -0.60 2.04
0 3 -5 0.00 1.79
0 3 -6 0.52 1.76
0 3 -7 0.73 1.95
0 3 -8 -3.27 2.32
0 3 -9 2.90 2.73
0 3 -10 5.60 2.80
0 3 -11 1.32 2.84
0 3 -12 -10.29 7.82
0 3 -13 1.56 3.12
0 3 -14 -5.34 3.36
0 3 -15 0.61 6.61
0 3 -16 4.55 4.01
0 3 -17 2.44 4.84
0 3 -18 -4.10 5.93
0 4 -18 -7.22 5.95
0 4 -17 11.39 5.18
0 4 -16 128.87 8.99
0 4 -15 1762.99 25.36
0 4 -14 0.87 3.98
0 4 -13 69.51 5.89
0 4 -12 198.61 8.32
0 4 -11 69.35 5.59
0 4 -10 1316.24 18.64
0 4 -9 1339.18 18.03
0 4 -8 -2.98 2.39
0 4 -7 10.95 2.62
0 4 -6 8.17 3.49
0 4 -5 663.79 10.72
0 4 -4 4.08 2.23
0 4 -3 5583.35 100.49
0 4 -2 7650.62 111.40
0 4 -1 230.83 5.53
0 4 0 5053.29 86.78
0 4 1 217.87 5.43
0 4 2 7074.02 106.56
0 4 4 1.87 2.26
0 4 5 615.58 10.35
0 4 6 -7.46 3.97
0 4 7 12.87 2.57
0 4 8 0.35 2.20
0 4 9 1256.46 17.29
0 4 10 1210.13 17.96
0 4 11 62.98 5.11
0 4 12 159.48 8.30
0 4 13 70.35 5.76
0 4 14 -1.74 4.01
0 4 15 1617.13 24.72
0 4 16 112.61 9.14
0 4 17 6.06 5.51
0 4 18 7.98 5.47
0 4 19 544.83 17.49
0 4 20 -16.35 6.80
0 4 21 48.88 7.90
0 4 22 40.20 7.20
0 4 23 10.25 6.68
0 4 24 62.34 8.72
0 4 25 -17.75 8.04
0 4 26 2.42 7.64
0 4 27 -6.36 8.44
0 5 27 7.09 8.18
0 5 26 -13.47 7.09
0 5 25 1.16 7.16
0 5 24 0.55 9.36
0 5 23 -3.13 6.76
0 5 22 5.92 5.67
0 5 21 5.59 5.71
0 5 20 -6.59 6.68
0 5 19 7.87 10.64
0 5 18 8.57 5.28
0 5 17 -0.73 4.80
0 5 16 -5.49 4.63
0 5 15 2.57 4.99
0 5 14 -7.20 4.15
0 5 13 -1.68 3.81
0 5 12 0.78 3.28
0 5 11 -0.24 3.11
0 5 10 -5.57 3.45
0 5 9 3.08 2.59
0 5 8 0.76 2.44
0 5 7 2.26 2.26
0 5 6 -2.08 2.34
0 5 5 -1.47 2.43
0 5 4 -2.85 1.90
0 5 3 -1.39 1.65
0 5 2 0.36 1.86
0 5 1 -1.15 1.47
0 5 -1 -1.04 1.53
0 5 -2 0.60 1.89
0 5 -3 -2.28 1.70
0 5 -4 -0.81 2.08
0 5 -5 -0.59 2.32
0 5 -6 1.60 1.98
0 5 -7 0.87 2.25
0 5 -8 -0.38 2.61
0 5 -9 -5.55 3.08
0 5 -10 0.22 3.33
0 5 -11 7.46 2.96
0 5 -12 -4.15 3.56
0 5 -13 -3.35 3.49
0 5 -14 -12.28 4.71
0 5 -15 1.28 5.43
0 5 -16 -3.77 4.91
0 5 -17 0.00 4.99
0 5 -18 -3.50 5.99
0 6 -18 69.71 9.05
0 6 -17 167.47 10.08
0 6 -16 5.32 4.56
0 6 -15 0.67 6.28
0 6 -14 392.37 12.78
0 6 -13 248.07 9.88
0 6 -12 59.80 5.45
0 6 -11 -1.02 3.38
0 6 -10 670.73 14.57
0 6 -9 1498.82 20.12
0 6 -8 834.61 14.89
0 6 -7 375.46 9.92
0 6 -6 382.01 9.29
0 6 -5 718.52 12.59
0 6 -4 20.97 2.80
0 6 -3 1784.74 23.18
0 6 -2 17.92 2.26
0 6 -1 64.81 4.01
0 6 1 72.30 4.06
0 6 2 14.08 2.55
0 6 3 1736.13 22.25
0 6 4 25.68 3.05
0 6 5 671.68 12.00
0 6 6 330.41 9.15
0 6 7 347.20 9.51
0 6 8 778.07 14.06
0 6 9 1351.75 19.30
0 6 10 600.39 13.64
0 6 11 -3.31 3.47
0 6 12 53.56 5.13
0 6 13 225.43 9.65
0 6 14 367.02 12.38
0 6 15 -8.00 5.77
0 6 16 0.71 4.71
0 6 17 164.56 9.73
0 6 18 80.58 8.48
0 6 19 8.08 5.22
0 6 20 31.98 7.31
0 6 21 35.75 7.79
0 6 22 5.54 6.96
0 6 23 15.96 7.26
0 6 24 -1.12 6.83
0 6 25 71.59 10.96
0 6 26 0.62 7.81
0 6 27 28.17 8.52
0 7 26 -2.54 6.66
0 7 25 -0.60 7.07
0 7 24 -6.89 7.03
0 7 23 0.00 7.43
0 7 22 -0.52 6.18
0 7 21 -0.49 6.09
0 7 20 6.49 6.35
0 7 19 -3.51 5.44
0 7 18 -8.28 5.62
0 7 17 -3.52 5.20
0 7 16 1.47 4.58
0 7 15 5.91 5.44
0 7 14 -1.63 4.47
0 7 13 3.07 3.50
0 7 12 5.49 3.75
0 7 11 0.00 3.81
0 7 10 -7.12 3.70
0 7 9 -1.19 3.42
0 7 8 2.24 3.14
0 7 7 -3.79 6.12
0 7 6 1.59 2.59
0 7 5 -1.50 2.14
0 7 4 3.03 2.39
0 7 3 -0.86 2.18
0 7 2 1.66 2.21
0 7 1 -1.62 2.08
0 7 -1 -0.32 1.89
0 7 -2 -0.83 2.08
0 7 -3 -0.17 2.71
0 7 -4 0.00 2.27
0 7 -5 -0.75 2.31
0 7 -6 0.00 2.66
0 7 -7 -7.57 6.46
0 7 -8 2.46 2.89
0 7 -9 5.01 3.17
0 7 -10 -3.30 3.88
0 7 -11 4.06 3.78
0 7 -12 -4.04 3.58
0 7 -13 0.61 3.93
0 7 -14 2.94 4.63
0 7 -15 -0.35 4.80
0 7 -16 13.27 4.04
0 7 -17 3.91 4.85
0 7 -18 -7.04 5.09
0 8 -18 7.72 6.22
0 8 -17 13.81 5.14
0 8 -16 17.67 5.70
0 8 -15 126.39 8.39
0 8 -14 350.65 12.64
0 8 -13 -0.65 4.47
0 8 -12 0.31 9.15
0 8 -11 448.40 12.71
0 8 -10 255.70 10.00
0 8 -9 638.22 14.54
0 8 -8 167.15 8.86
0 8 -7 12.01 3.18
0 8 -6 177.44 7.39
0 8 -5 -0.63 3.10
0 8 -4 76.30 10.86
0 8 -3 73.96 4.75
0 8 -2 225.80 7.92
0 8 -1 271.22 8.17
0 8 0 233.54 9.24
0 8 1 260.60 8.06
0 8 2 210.67 7.53
0 8 3 62.11 4.45
0 8 5 8.60 2.66
0 8 6 152.72 6.87
0 8 7 1.16 3.53
0 8 8 154.35 8.46
0 8 9 603.39 13.89
0 8 10 247.17 9.71
0 8 11 401.36 12.21
0 8 12 13.77 8.02
0 8 13 7.46 4.48
0 8 14 297.70 12.03
0 8 15 100.31 8.30
0 8 16 8.46 5.62
0 8 17 8.94 5.33
0 8 18 9.45 5.92
0 8 19 21.76 6.48
0 8 20 0.00 5.62
0 8 21 21.18 7.81
0 8 22 71.72 8.78
0 8 23 15.66 7.07
0 8 24 -1.76 7.96
0 8 25 -12.99 8.37
0 8 26 10.39 6.30
0 9 25 -4.44 8.05
0 9 24 -5.44 7.18
0 9 23 -1.15 7.68
0 9 22 0.55 5.87
0 9 21 1.04 6.79
0 9 20 -5.94 6.53
0 9 19 1.88 5.36
0 9 18 -1.34 5.52
0 9 17 0.00 6.23
0 9 16 6.43 5.45
0 9 15 1.14 5.87
0 9 14 -1.45 4.37
0 9 13 -1.71 4.46
0 9 12 -0.33 5.57
0 9 11 7.10 3.61
0 9 10 1.46 3.98
0 9 9 5.85 5.89
0 9 8 6.90 2.78
0 9 7 3.04 2.91
0 9 6 -13.82 3.96
0 9 5 -1.86 2.78
0 9 4 -4.51 3.20
0 9 3 -2.85 2.67
0 9 2 0.43 2.37
0 9 1 -3.39 2.40
0 9 0 -13.92 6.41
0 9 -1 -2.54 2.26
0 9 -2 -0.86 2.43
0 9 -3 5.04 2.67
0 9 -4 -4.50 2.85
0 9 -5 0.47 2.57
0 9 -6 0.24 3.09
0 9 -7 -4.30 3.05
0 9 -8 1.59 3.04
0 9 -9 1.11 5.93
0 9 -10 2.93 4.10
0 9 -11 0.00 3.70
0 9 -12 -1.95 5.57
0 9 -13 2.40 4.13
0 9 -14 2.89 4.54
0 9 -15 3.05 5.85
0 9 -16 -2.01 5.49
0 9 -17 -0.42 6.63
0 9 -18 -2.68 5.99
0 10 -18 54.88 8.11
0 10 -17 124.36 10.22
0 10 -16 115.39 9.44
0 10 -15 2.00 6.12
0 10 -14 14.49 6.08
0 10 -13 3.99 4.94
0 10 -12 203.30 10.41
0 10 -11 9.89 5.17
0 10 -10 229.57 10.99
0 10 -9 72.13 6.46
0 10 -8 14.39 3.55
0 10 -7 132.37 7.56
0 10 -6 2.66 3.30
0 10 -5 56.12 6.53
0 10 -4 453.70 12.01
0 10 -3 23.70 3.98
0 10 -2 21.14 4.19
0 10 -1 2.14 2.76
0 10 0 323.99 11.16
0 10 1 -2.61 2.92
0 10 2 27.39 3.72
0 10 3 20.78 3.93
0 10 4 418.89 12.00
0 10 5 50.48 6.11
0 10 6 2.40 2.88
0 10 7 128.03 6.85
0 10 8 8.06 3.97
0 10 9 66.17 5.74
0 10 10 242.96 10.78
0 10 11 7.92 5.24
0 10 12 194.48 9.84
0 10 13 -2.18 4.95
0 10 14 16.03 4.77
0 10 15 0.40 5.48
0 10 16 133.61 8.99
0 10 17 109.41 9.84
0 10 18 44.22 8.13
0 10 19 17.60 6.45
0 10 20 14.89 6.99
0 10 21 1.08 6.52
0 10 22 6.23 6.77
0 10 23 22.56 8.14
0 10 24 19.92 7.21
0 10 25 -2.61 8.04
0 11 24 10.92 6.65
0 11 23 3.07 7.18
0 11 22 3.52 7.46
0 11 21 0.56 6.31
0 11 20 11.75 5.65
0 11 19 -2.55 6.14
0 11 18 -0.97 6.03
0 11 17 -7.89 6.03
0 11 16 10.18 5.62
0 11 15 2.96 5.87
0 11 14 0.40 5.34
0 11 13 4.63 5.00
0 11 12 1.84 5.33
0 11 11 -7.41 7.20
0 11 10 -4.39 4.89
0 11 9 0.65 3.58
0 11 8 -5.00 4.07
0 11 7 0.00 3.83
0 11 6 0.00 3.42
0 11 5 -3.11 3.68
0 11 4 3.87 3.20
0 11 3 -5.41 3.29
0 11 2 -5.07 3.69
0 11 1 0.00 2.90
0 11 0 1.05 7.49
0 11 -1 -3.96 3.96
0 11 -2 -6.13 3.76
0 11 -3 -0.27 3.37
0 11 -4 -4.69 3.52
0 11 -5 1.98 3.41
0 11 -6 -0.58 3.82
0 11 -7 1.50 4.16
0 11 -8 9.36 3.58
0 11 -9 -1.30 4.52
0 11 -10 -0.68 4.58
0 11 -11 9.16 6.65
0 11 -12 5.15 4.80
0 11 -13 -7.32 5.72
0 11 -14 -5.64 5.64
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11 6 6 5.76 7.29
11 6 5 5.12 6.62
11 6 4 3.38 6.18
11 6 3 -2.24 7.03
11 6 2 3.34 7.21
11 6 1 3.88 6.39
11 6 0 3.32 6.64
11 6 -1 -1.66 6.72
11 6 -2 12.23 6.76
11 6 -3 -7.83 7.33
11 6 -4 -2.25 7.21
11 6 -5 -9.10 8.05
11 6 -6 -1.15 8.06
11 6 -7 8.17 7.87
11 6 -8 -3.56 7.55
11 6 -9 2.41 7.49
11 6 -10 2.46 7.48
11 6 -11 18.20 8.94
11 6 -12 10.91 9.00
11 6 -13 5.91 8.44
11 5 -13 0.65 8.55
11 5 -12 12.62 9.06
11 5 -11 12.96 6.84
11 5 -10 3.02 7.07
11 5 -9 5.93 6.91
11 5 -8 2.91 7.52
11 5 -7 -13.75 7.43
11 5 -6 -1.70 7.39
11 5 -5 13.96 7.39
11 5 -4 7.19 6.66
11 5 -3 8.78 7.07
11 5 -2 13.64 7.09
11 5 -1 3.81 6.94
11 5 0 -2.17 6.43
11 5 1 4.35 6.57
11 5 2 3.27 6.94
11 5 3 7.13 7.50
11 5 4 -3.32 7.54
11 5 5 -7.82 6.66
11 5 6 -11.88 7.90
11 5 7 2.30 7.26
11 5 8 8.16 5.95
11 5 9 -5.94 8.27
11 5 10 -0.61 6.43
11 5 11 -1.85 7.02
11 5 12 13.91 6.51
11 5 13 -5.18 8.49
11 4 14 5.24 9.13
11 4 13 -18.53 8.45
11 4 12 1.25 7.99
11 4 11 4.88 6.22
11 4 10 -5.97 7.21
11 4 9 -4.68 7.12
11 4 8 -1.72 7.11
11 4 7 -8.48 6.85
11 4 6 31.75 7.02
11 4 5 1.65 6.39
11 4 4 14.70 6.74
11 4 3 0.54 6.77
11 4 2 20.40 8.14
11 4 1 -17.66 7.24
11 4 0 14.43 5.93
11 4 -1 1.07 7.33
11 4 -2 21.47 7.51
11 4 -3 -1.62 7.30
11 4 -4 5.99 7.75
11 4 -5 2.20 6.95
11 4 -6 8.90 8.37
11 4 -7 1.69 6.84
11 4 -8 7.46 6.62
11 4 -9 14.02 7.01
11 4 -10 19.66 8.19
11 4 -11 15.22 7.33
11 4 -12 -8.09 9.86
11 4 -13 14.67 8.53
11 4 -14 5.23 8.83
11 3 -14 4.53 9.27
11 3 -13 -18.94 9.41
11 3 -12 16.02 7.74
11 3 -11 10.84 7.52
11 3 -10 7.07 7.77
11 3 -9 -4.62 7.83
11 3 -8 1.13 7.65
11 3 -7 -8.37 7.55
11 3 -6 30.24 7.99
11 3 -5 25.52 7.96
11 3 -4 7.52 7.13
11 3 -3 45.84 8.29
11 3 -2 2.12 6.70
11 3 -1 5.81 6.70
11 3 0 1.58 6.90
11 3 1 10.57 5.83
11 3 2 -9.01 7.01
11 3 3 32.00 8.47
11 3 4 -3.76 6.70
11 3 5 13.04 7.87
11 3 6 25.31 8.70
11 3 7 -1.12 6.79
11 3 8 3.41 6.52
11 3 9 5.78 6.74
11 3 10 3.54 5.96
11 3 11 -4.82 7.48
11 3 12 -7.41 7.41
11 3 13 5.06 7.32
11 3 14 5.84 7.02
11 2 14 33.50 8.30
11 2 13 3.14 7.81
11 2 12 14.08 7.17
11 2 11 0.60 7.78
11 2 10 15.22 7.76
11 2 9 12.62 6.23
11 2 8 12.38 7.51
11 2 7 29.34 7.15
11 2 6 1.09 7.24
11 2 5 17.77 8.90
11 2 4 18.65 7.81
11 2 3 0.53 7.46
11 2 2 1.05 7.32
11 2 1 -14.66 8.14
11 2 0 2.09 6.86
11 2 -1 -10.99 7.74
11 2 -2 0.53 7.63
11 2 -3 3.70 7.34
11 2 -4 30.89 8.91
11 2 -5 17.76 8.79
11 2 -6 12.53 7.41
11 2 -7 18.25 8.83
11 2 -8 17.43 7.69
11 2 -9 10.31 7.15
11 2 -10 28.05 8.35
11 2 -11 2.39 8.23
11 2 -12 15.89 7.54
11 2 -13 3.13 8.52
11 2 -14 45.01 10.87
11 1 -14 4.48 8.32
11 1 -13 11.23 8.78
11 1 -12 0.00 8.16
11 1 -11 -4.76 7.93
11 1 -10 -4.65 7.22
11 1 -9 30.20 8.12
11 1 -8 5.03 7.69
11 1 -7 19.80 6.60
11 1 -6 11.93 7.11
11 1 -5 2.14 8.26
11 1 -4 -2.65 7.58
11 1 -3 30.47 8.10
11 1 -2 -3.13 7.24
11 1 -1 32.79 7.27
11 1 0 2.08 6.45
11 1 1 36.43 7.17
11 1 2 8.36 7.09
11 1 3 2.63 6.91
11 1 4 2.12 6.83
11 1 5 9.11 7.96
11 1 6 -4.34 7.94
11 1 7 12.12 6.97
11 1 8 -6.16 6.60
11 1 9 19.97 7.63
11 1 10 -1.16 7.08
11 1 11 -1.19 6.94
11 1 12 -5.49 7.39
11 1 13 -3.75 7.34
11 1 14 -1.92 8.39
11 0 14 28.18 8.92
11 0 13 0.00 7.17
11 0 12 8.52 6.88
11 0 11 -2.97 6.70
11 0 10 -8.72 7.19
11 0 9 -2.85 6.72
11 0 8 3.91 6.73
11 0 7 8.80 5.66
11 0 6 59.58 8.83
11 0 5 9.62 6.28
11 0 4 3.17 6.08
11 0 3 -9.44 6.92
11 0 2 44.32 8.96
11 0 1 4.16 6.77
11 0 0 15.57 7.19
11 0 -1 -6.75 7.29
11 0 -2 33.36 9.00
11 0 -3 8.91 6.53
11 0 -4 -19.03 7.98
11 0 -5 4.27 6.97
11 0 -6 68.72 9.66
11 0 -7 -16.47 7.61
11 0 -8 9.49 7.60
11 0 -9 6.26 6.66
11 0 -10 19.16 8.11
11 0 -11 -2.37 8.01
11 0 -12 13.97 7.99
11 0 -13 1.87 8.70
11 0 -14 19.82 9.42
11 0 -15 -3.28 9.12
12 0 -10 -16.80 10.46
12 0 -9 0.00 7.77
12 0 -8 6.87 8.07
12 0 -7 5.54 7.76
12 0 -6 1.21 8.72
12 0 -5 -9.01 8.12
12 0 -4 17.85 8.50
12 0 -3 5.91 7.75
12 0 -2 104.04 12.34
12 0 -1 -1.17 7.69
12 0 0 39.81 9.97
12 0 1 -2.34 8.04
12 0 2 59.39 12.21
12 0 3 14.78 7.26
12 0 4 28.58 7.00
12 0 5 2.40 7.01
12 0 6 10.94 8.15
12 0 7 -4.31 7.52
12 0 8 2.50 7.45
12 0 9 2.54 6.73
12 0 10 -1.94 7.18
12 1 10 7.78 7.78
12 1 9 -3.18 6.82
12 1 8 5.63 7.11
12 1 7 18.50 7.85
12 1 6 -6.09 7.20
12 1 5 -4.21 7.64
12 1 4 -14.91 7.98
12 1 3 4.14 7.56
12 1 2 -2.36 7.95
12 1 1 9.39 7.56
12 1 0 4.69 7.37
12 1 -1 8.22 7.52
12 1 -2 -6.48 8.05
12 1 -3 14.79 6.98
12 1 -4 2.38 6.80
12 1 -5 -0.60 7.49
12 1 -6 -3.65 8.02
12 1 -7 7.39 7.24
12 1 -8 6.88 7.63
12 1 -9 0.64 8.41
12 1 -10 18.77 9.08
12 2 -10 -9.10 8.67
12 2 -9 -1.92 8.20
12 2 -8 2.51 8.24
12 2 -7 16.09 8.49
12 2 -6 3.67 7.92
12 2 -5 1.21 8.29
12 2 -4 -2.99 8.70
12 2 -3 2.38 9.17
12 2 -2 0.00 7.67
12 2 -1 7.67 8.69
12 2 0 4.71 6.97
12 2 1 -11.80 8.38
12 2 2 -5.33 7.46
12 2 3 1.78 9.04
12 2 4 1.20 7.53
12 2 5 -4.23 7.08
12 2 6 -1.22 7.29
12 2 7 -13.63 7.17
12 2 8 10.06 5.90
12 2 9 4.47 7.03
12 2 10 6.51 6.70
12 3 10 23.60 7.00
12 3 9 5.80 6.60
12 3 8 -1.90 7.68
12 3 7 3.75 6.84
12 3 6 -16.03 7.50
12 3 5 -14.63 8.31
12 3 4 10.87 7.69
12 3 3 37.78 8.75
12 3 2 17.90 9.47
12 3 1 2.97 7.55
12 3 0 -4.75 7.51
12 3 -1 -3.57 7.14
12 3 -2 41.75 9.08
12 3 -3 41.96 9.25
12 3 -4 10.87 8.23
12 3 -5 -8.53 8.13
12 3 -6 -6.16 7.89
12 3 -7 -0.62 7.77
12 3 -8 21.52 7.70
12 3 -9 13.51 8.41
12 3 -10 28.80 8.68
12 4 -9 14.94 8.98
12 4 -8 -1.92 9.33
12 4 -7 -6.93 8.05
12 4 -6 -12.45 8.44
12 4 -5 2.46 8.22
12 4 -4 13.43 7.72
12 4 -3 -9.09 9.56
12 4 -2 6.63 7.79
12 4 -1 14.43 9.08
12 4 0 -8.41 7.88
12 4 1 15.64 7.98
12 4 2 -11.46 8.07
12 4 3 -4.85 8.22
12 4 4 -0.61 8.44
12 4 5 9.24 7.47
12 4 6 -11.21 7.48
12 4 7 9.46 6.28
12 4 8 -5.76 7.10
12 4 9 11.71 8.13
12 5 8 7.78 8.10
12 5 7 -13.43 8.36
12 5 6 -4.42 7.71
12 5 5 3.12 7.47
12 5 4 -3.72 8.58
12 5 3 -1.23 8.06
12 5 2 5.51 7.26
12 5 1 1.83 7.54
12 5 0 -7.31 7.90
12 5 -1 -3.66 8.71
12 5 -2 -15.90 7.88
12 5 -3 -12.29 8.34
12 5 -4 -0.62 7.40
12 5 -5 -16.23 8.33
12 5 -6 6.94 8.44
12 5 -7 19.80 7.03
12 5 -8 0.00 8.84
12 6 -7 2.60 8.66
12 6 -6 1.92 7.78
12 6 -5 -3.17 7.80
12 6 -4 4.40 7.88
12 6 -3 16.25 7.55
12 6 -2 0.62 6.31
12 6 -1 19.23 7.92
12 6 0 6.82 7.56
12 6 1 21.71 7.26
12 6 2 -5.60 8.55
12 6 3 -1.25 7.45
12 6 4 3.78 7.07
12 6 5 -3.18 7.96
12 6 6 2.57 7.65
12 6 7 -5.85 7.72
12 7 6 -1.31 8.58
12 7 5 16.19 7.30
12 7 4 1.28 7.26
12 7 3 7.01 8.09
12 7 2 8.88 9.24
12 7 1 7.59 6.93
12 7 0 -0.63 7.40
12 7 -1 -5.69 8.83
12 7 -2 19.66 8.95
12 7 -3 -5.10 8.50
12 7 -4 3.21 7.99
12 7 -5 3.23 8.21
12 7 -6 1.31 9.10
12 8 -4 -8.52 8.00
12 8 -3 13.68 8.67
12 8 -2 11.02 7.42
12 8 -1 -17.46 9.17
12 8 0 18.74 7.73
12 8 1 -3.23 7.46
12 8 2 -1.95 8.63
12 8 3 5.21 7.88
12 8 4 6.56 6.56
13 1 0 -4.60 8.03
13 0 1 13.80 7.11
13 0 0 -11.82 8.81
13 0 -1 -5.91 7.97
0 0 0 0.00 0.00
_computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)'
;
_shelx_hkl_checksum 21816
_shelx_res_file
;
TITL etr-bz_a.res in P-1 New:Pbca
etr-bz.res
created by SHELXL-2018/3 at 16:43:49 on 29-Apr-2024
CELL 0.71073 10.792 18.713 23.299 90 90 90
ZERR 8 0.0002 0.0004 0.0005 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,0.5+Y,0.5-Z
SFAC C H Cl N O S
UNIT 200 168 8 16 32 8
L.S. 90
PLAN 2
SIZE 0.46 0.1 0.08
TEMP 20(2)
CONF
BOND $H
MORE -1
fmap 2
acta
OMIT 0 2 0
OMIT 1 1 1
REM
REM
REM
WGHT 0.077800
FVAR 0.30840
CL1 3 0.698797 0.045043 0.284057 11.00000 0.07375 0.06280 =
0.06918 0.00427 -0.01358 0.00954
S1 6 0.434930 0.265561 -0.047381 11.00000 0.06503 0.08293 =
0.02989 0.00804 -0.00044 0.00185
O2 5 0.520212 0.321824 -0.054692 11.00000 0.18648 0.22690 =
0.06316 0.06780 -0.03634 -0.13883
O1 5 0.450284 0.203165 -0.080329 11.00000 0.18992 0.11392 =
0.03282 -0.00399 0.01036 0.07876
N1 4 0.413867 0.175880 0.300432 11.00000 0.07721 0.04505 =
0.03033 0.00329 0.00097 0.00169
N2 4 0.203618 0.357916 0.287564 11.00000 0.05238 0.04373 =
0.04484 -0.00547 -0.00293 0.00058
C12 1 0.396565 0.200496 0.246368 11.00000 0.05588 0.03887 =
0.02902 -0.00127 0.00028 -0.00489
C1 1 0.436150 0.240521 0.025860 11.00000 0.05528 0.05721 =
0.02503 0.00117 0.00620 -0.00262
C13 1 0.299474 0.256488 0.241547 11.00000 0.04533 0.04247 =
0.03271 0.00006 0.00288 -0.00403
C4 1 0.452208 0.199780 0.139689 11.00000 0.04933 0.04865 =
0.02691 -0.00216 0.00201 -0.00060
C2 1 0.473276 0.289336 0.066787 11.00000 0.07086 0.05141 =
0.04219 0.00805 -0.00476 -0.00916
AFIX 43
H2 2 0.493560 0.335778 0.056123 11.00000 -1.20000
AFIX 0
C9 1 0.559615 0.124846 0.211682 11.00000 0.06549 0.04445 =
0.03566 -0.00501 0.00372 0.00564
AFIX 43
H9 2 0.607309 0.106448 0.181901 11.00000 -1.20000
AFIX 0
C3 1 0.480214 0.268769 0.124035 11.00000 0.07053 0.04768 =
0.03361 -0.00053 -0.00652 -0.01474
AFIX 43
H3 2 0.503856 0.301751 0.151813 11.00000 -1.20000
AFIX 0
C8 1 0.467166 0.174986 0.200746 11.00000 0.05125 0.03996 =
0.02905 -0.00275 -0.00048 -0.00437
C10 1 0.579015 0.103094 0.267238 11.00000 0.06007 0.03747 =
0.04325 0.00046 -0.01195 -0.00037
C6 1 0.405381 0.172719 0.040862 11.00000 0.08960 0.05407 =
0.03260 -0.00789 0.00284 -0.01092
AFIX 43
H6 2 0.378621 0.140473 0.013133 11.00000 -1.20000
AFIX 0
C15 1 0.128667 0.366630 0.241941 11.00000 0.04341 0.05012 =
0.05110 0.00410 0.00639 -0.00451
C11 1 0.502935 0.128927 0.310154 11.00000 0.07576 0.04666 =
0.03707 0.00542 -0.00824 0.00264
AFIX 43
H11 2 0.514870 0.112605 0.347448 11.00000 -1.20000
AFIX 0
C5 1 0.414159 0.151808 0.098013 11.00000 0.09236 0.04531 =
0.03952 -0.00350 0.00089 -0.01560
AFIX 43
H5 2 0.394291 0.105184 0.108323 11.00000 -1.20000
AFIX 0
C14 1 0.285884 0.305145 0.286445 11.00000 0.05505 0.04793 =
0.03367 -0.00142 -0.00214 -0.00503
AFIX 43
H14 2 0.338253 0.300286 0.317904 11.00000 -1.20000
AFIX 0
C7 1 0.288752 0.297326 -0.060297 11.00000 0.11394 0.16096 =
0.05825 0.00895 -0.00820 0.06489
AFIX 137
H7A 2 0.274659 0.339342 -0.037574 11.00000 -1.50000
H7B 2 0.228992 0.261414 -0.050318 11.00000 -1.50000
H7C 2 0.280659 0.309029 -0.100238 11.00000 -1.50000
AFIX 0
C18 1 0.037439 0.426549 0.245305 11.00000 0.06935 0.06162 =
0.08979 -0.00286 -0.00597 0.00660
AFIX 137
H18A 2 -0.029677 0.413189 0.270127 11.00000 -1.50000
H18B 2 0.005813 0.436600 0.207650 11.00000 -1.50000
H18C 2 0.077569 0.468353 0.260301 11.00000 -1.50000
AFIX 0
C16 1 0.133923 0.320328 0.195940 11.00000 0.05414 0.06616 =
0.03822 0.00198 -0.00565 -0.00681
AFIX 43
H16 2 0.079794 0.326161 0.165236 11.00000 -1.20000
AFIX 0
C17 1 0.218460 0.265859 0.195315 11.00000 0.05000 0.05691 =
0.03445 -0.00550 0.00483 -0.01079
AFIX 43
H17 2 0.222059 0.234995 0.164074 11.00000 -1.20000
AFIX 0
O3 5 0.181883 0.423858 0.389607 11.00000 0.07899 0.08800 =
0.06137 -0.03035 0.01324 -0.01810
AFIX 147
H3A 2 0.192143 0.411321 0.356220 11.00000 -1.50000
AFIX 0
O4 5 0.354203 0.484967 0.373042 11.00000 0.12909 0.12858 =
0.06354 -0.01410 0.03369 -0.05427
C19 1 0.270790 0.467010 0.404656 11.00000 0.06802 0.05585 =
0.05397 -0.00516 0.00228 -0.00662
C20 1 0.260504 0.493337 0.465133 11.00000 0.05828 0.03943 =
0.04744 -0.00013 -0.00477 -0.00479
C21 1 0.165078 0.475750 0.500372 11.00000 0.08527 0.07259 =
0.05796 -0.01450 0.00494 -0.02259
AFIX 43
H21 2 0.102760 0.445771 0.486944 11.00000 -1.20000
AFIX 0
C23 1 0.250652 0.545269 0.575738 11.00000 0.11509 0.07070 =
0.05259 -0.00571 -0.00442 -0.00258
AFIX 43
H23 2 0.246163 0.563413 0.612840 11.00000 -1.20000
AFIX 0
C25 1 0.352132 0.536539 0.486576 11.00000 0.08191 0.07458 =
0.07290 -0.00057 -0.00082 -0.02335
AFIX 43
H25 2 0.418658 0.548698 0.463158 11.00000 -1.20000
AFIX 0
C22 1 0.158945 0.501604 0.555809 11.00000 0.09966 0.09910 =
0.06233 -0.01573 0.01999 -0.02412
AFIX 43
H22 2 0.092771 0.489347 0.579407 11.00000 -1.20000
AFIX 0
C24 1 0.348175 0.562337 0.541796 11.00000 0.09455 0.08618 =
0.06527 -0.01357 -0.01865 -0.02248
AFIX 43
H24 2 0.411671 0.591152 0.555678 11.00000 -1.20000
AFIX 0
HKLF 4
REM etr-bz_a.res in P-1 New:Pbca
REM wR2 = 0.1922, GooF = S = 1.015, Restrained GooF = 1.015 for all data
REM R1 = 0.0681 for 2113 Fo > 4sig(Fo) and 0.1591 for all 4277 data
REM 301 parameters refined using 0 restraints
END
WGHT 0.0778 0.0000
REM Highest difference peak 0.293, deepest hole -0.567, 1-sigma level 0.090
Q1 1 0.4354 0.3504 -0.0339 11.00000 0.05 0.29
Q2 1 0.2305 0.1871 -0.0539 11.00000 0.05 0.27
;
_shelx_res_checksum 93364
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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
Cl Cl1 0.69880(12) 0.04504(7) 0.28406(5) 0.0686(4) Uani d 1 . .
S S1 0.43493(12) 0.26556(7) -0.04738(5) 0.0593(4) Uani d 1 . .
O O2 0.5202(5) 0.3218(3) -0.05469(17) 0.159(2) Uani d 1 . .
O O1 0.4503(4) 0.2032(2) -0.08033(14) 0.1122(17) Uani d 1 . .
N N1 0.4139(4) 0.17588(19) 0.30043(14) 0.0509(10) Uani d 1 . .
N N2 0.2036(3) 0.35792(18) 0.28756(15) 0.0470(9) Uani d 1 . .
C C12 0.3966(4) 0.2005(2) 0.24637(17) 0.0413(10) Uani d 1 . .
C C1 0.4362(4) 0.2405(2) 0.02586(17) 0.0458(11) Uani d 1 . .
C C13 0.2995(4) 0.2565(2) 0.24155(16) 0.0402(10) Uani d 1 . .
C C4 0.4522(4) 0.1998(2) 0.13969(16) 0.0416(10) Uani d 1 . .
C C2 0.4733(4) 0.2893(2) 0.06679(18) 0.0548(13) Uani d 1 . .
H H2 0.493560 0.335778 0.056123 0.066 Uiso calc 1 . .
C C9 0.5596(4) 0.1248(2) 0.21168(17) 0.0485(12) Uani d 1 . .
H H9 0.607309 0.106448 0.181901 0.058 Uiso calc 1 . .
C C3 0.4802(4) 0.2688(2) 0.12403(17) 0.0506(12) Uani d 1 . .
H H3 0.503856 0.301751 0.151813 0.061 Uiso calc 1 . .
C C8 0.4672(4) 0.1750(2) 0.20075(16) 0.0401(10) Uani d 1 . .
C C10 0.5790(4) 0.1031(2) 0.26724(18) 0.0469(11) Uani d 1 . .
C C6 0.4054(5) 0.1727(2) 0.04086(18) 0.0588(13) Uani d 1 . .
H H6 0.378621 0.140473 0.013133 0.071 Uiso calc 1 . .
C C15 0.1287(4) 0.3666(2) 0.2419(2) 0.0482(11) Uani d 1 . .
C C11 0.5029(5) 0.1289(2) 0.31015(19) 0.0532(12) Uani d 1 . .
H H11 0.514870 0.112605 0.347448 0.064 Uiso calc 1 . .
C C5 0.4142(5) 0.1518(2) 0.09801(18) 0.0591(13) Uani d 1 . .
H H5 0.394291 0.105184 0.108323 0.071 Uiso calc 1 . .
C C14 0.2859(4) 0.3051(2) 0.28645(17) 0.0455(11) Uani d 1 . .
H H14 0.338253 0.300286 0.317904 0.055 Uiso calc 1 . .
C C7 0.2888(6) 0.2973(4) -0.0603(2) 0.111(2) Uani d 1 . .
H H7A 0.274659 0.339342 -0.037574 0.167 Uiso calc 1 . .
H H7B 0.228992 0.261414 -0.050318 0.167 Uiso calc 1 . .
H H7C 0.280659 0.309029 -0.100238 0.167 Uiso calc 1 . .
C C18 0.0374(4) 0.4265(3) 0.2453(2) 0.0736(15) Uani d 1 . .
H H18A -0.029677 0.413189 0.270127 0.110 Uiso calc 1 . .
H H18B 0.005813 0.436600 0.207650 0.110 Uiso calc 1 . .
H H18C 0.077569 0.468353 0.260301 0.110 Uiso calc 1 . .
C C16 0.1339(4) 0.3203(3) 0.19594(18) 0.0528(12) Uani d 1 . .
H H16 0.079794 0.326161 0.165236 0.063 Uiso calc 1 . .
C C17 0.2185(4) 0.2659(2) 0.19531(17) 0.0471(11) Uani d 1 . .
H H17 0.222059 0.234995 0.164074 0.057 Uiso calc 1 . .
O O3 0.1819(3) 0.4239(2) 0.38961(14) 0.0761(10) Uani d 1 . .
H H3A 0.192143 0.411321 0.356220 0.114 Uiso calc 1 . .
O O4 0.3542(4) 0.4850(2) 0.37304(17) 0.1071(16) Uani d 1 . .
C C19 0.2708(5) 0.4670(3) 0.4047(2) 0.0593(13) Uani d 1 . .
C C20 0.2605(4) 0.4933(2) 0.46513(18) 0.0484(11) Uani d 1 . .
C C21 0.1651(6) 0.4758(3) 0.5004(2) 0.0719(16) Uani d 1 . .
H H21 0.102760 0.445771 0.486944 0.086 Uiso calc 1 . .
C C23 0.2507(6) 0.5453(3) 0.5757(2) 0.0795(17) Uani d 1 . .
H H23 0.246163 0.563413 0.612840 0.095 Uiso calc 1 . .
C C25 0.3521(5) 0.5365(3) 0.4866(2) 0.0765(16) Uani d 1 . .
H H25 0.418658 0.548698 0.463158 0.092 Uiso calc 1 . .
C C22 0.1589(6) 0.5016(3) 0.5558(2) 0.0870(18) Uani d 1 . .
H H22 0.092771 0.489347 0.579407 0.104 Uiso calc 1 . .
C C24 0.3482(6) 0.5623(3) 0.5418(2) 0.0820(17) Uani d 1 . .
H H24 0.411671 0.591152 0.555678 0.098 Uiso calc 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
Cl1 0.0738(9) 0.0628(8) 0.0692(8) 0.0095(7) -0.0136(7) 0.0043(6)
S1 0.0650(9) 0.0829(9) 0.0299(6) 0.0018(7) -0.0004(6) 0.0080(6)
O2 0.186(5) 0.227(5) 0.063(3) -0.139(5) -0.036(3) 0.068(3)
O1 0.190(5) 0.114(3) 0.033(2) 0.079(3) 0.010(2) -0.004(2)
N1 0.077(3) 0.045(2) 0.0303(19) 0.002(2) 0.0010(19) 0.0033(17)
N2 0.052(2) 0.044(2) 0.045(2) 0.0006(19) -0.0029(19) -0.0055(17)
C12 0.056(3) 0.039(2) 0.029(2) -0.005(2) 0.000(2) -0.0013(19)
C1 0.055(3) 0.057(3) 0.025(2) -0.003(2) 0.006(2) 0.001(2)
C13 0.045(3) 0.042(2) 0.033(2) -0.004(2) 0.003(2) 0.0001(19)
C4 0.049(3) 0.049(3) 0.027(2) -0.001(2) 0.0020(19) -0.0022(19)
C2 0.071(3) 0.051(3) 0.042(3) -0.009(3) -0.005(2) 0.008(2)
C9 0.065(3) 0.044(3) 0.036(3) 0.006(2) 0.004(2) -0.005(2)
C3 0.071(3) 0.048(3) 0.034(2) -0.015(2) -0.007(2) -0.001(2)
C8 0.051(3) 0.040(2) 0.029(2) -0.004(2) 0.000(2) -0.0027(18)
C10 0.060(3) 0.037(2) 0.043(3) 0.000(2) -0.012(2) 0.000(2)
C6 0.090(4) 0.054(3) 0.033(3) -0.011(3) 0.003(2) -0.008(2)
C15 0.043(3) 0.050(3) 0.051(3) -0.005(2) 0.006(2) 0.004(2)
C11 0.076(4) 0.047(3) 0.037(3) 0.003(3) -0.008(2) 0.005(2)
C5 0.092(4) 0.045(3) 0.040(3) -0.016(3) 0.001(3) -0.004(2)
C14 0.055(3) 0.048(3) 0.034(2) -0.005(2) -0.002(2) -0.001(2)
C7 0.114(5) 0.161(6) 0.058(3) 0.065(5) -0.008(4) 0.009(4)
C18 0.069(4) 0.062(3) 0.090(4) 0.007(3) -0.006(3) -0.003(3)
C16 0.054(3) 0.066(3) 0.038(3) -0.007(3) -0.006(2) 0.002(2)
C17 0.050(3) 0.057(3) 0.034(2) -0.011(2) 0.005(2) -0.006(2)
O3 0.079(2) 0.088(2) 0.061(2) -0.018(2) 0.0132(19) -0.030(2)
O4 0.129(4) 0.129(4) 0.064(3) -0.054(3) 0.034(3) -0.014(2)
C19 0.068(4) 0.056(3) 0.054(3) -0.007(3) 0.002(3) -0.005(3)
C20 0.058(3) 0.039(2) 0.047(3) -0.005(2) -0.005(2) 0.000(2)
C21 0.085(4) 0.073(4) 0.058(3) -0.023(3) 0.005(3) -0.015(3)
C23 0.115(5) 0.071(4) 0.053(3) -0.003(4) -0.004(4) -0.006(3)
C25 0.082(4) 0.075(4) 0.073(4) -0.023(3) -0.001(3) -0.001(3)
C22 0.100(5) 0.099(4) 0.062(4) -0.024(4) 0.020(3) -0.016(3)
C24 0.095(5) 0.086(4) 0.065(4) -0.022(4) -0.019(3) -0.014(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O2 S1 C1 . . 108.0(2) ?
O2 S1 C7 . . 108.7(4) ?
O1 S1 O2 . . 118.5(3) ?
O1 S1 C1 . . 107.8(2) ?
O1 S1 C7 . . 107.5(3) ?
C7 S1 C1 . . 105.6(2) ?
C11 N1 C12 . . 119.1(4) ?
C14 N2 C15 . . 118.4(4) ?
N1 C12 C13 . . 114.0(3) ?
N1 C12 C8 . . 121.2(4) ?
C8 C12 C13 . . 124.7(4) ?
C2 C1 S1 . . 119.6(3) ?
C6 C1 S1 . . 119.6(3) ?
C6 C1 C2 . . 120.8(4) ?
C14 C13 C12 . . 118.5(4) ?
C14 C13 C17 . . 115.5(4) ?
C17 C13 C12 . . 126.0(4) ?
C3 C4 C8 . . 121.1(4) ?
C3 C4 C5 . . 119.2(4) ?
C5 C4 C8 . . 119.7(4) ?
C1 C2 H2 . . 120.2 ?
C1 C2 C3 . . 119.7(4) ?
C3 C2 H2 . . 120.2 ?
C8 C9 H9 . . 120.6 ?
C10 C9 H9 . . 120.6 ?
C10 C9 C8 . . 118.8(4) ?
C4 C3 C2 . . 120.2(4) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C12 C8 C4 . . 123.9(4) ?
C12 C8 C9 . . 118.9(4) ?
C9 C8 C4 . . 117.2(4) ?
C9 C10 Cl1 . . 120.8(4) ?
C9 C10 C11 . . 119.2(4) ?
C11 C10 Cl1 . . 119.9(3) ?
C1 C6 H6 . . 120.2 ?
C1 C6 C5 . . 119.5(4) ?
C5 C6 H6 . . 120.2 ?
N2 C15 C18 . . 116.5(4) ?
N2 C15 C16 . . 120.9(4) ?
C16 C15 C18 . . 122.6(4) ?
N1 C11 C10 . . 122.7(4) ?
N1 C11 H11 . . 118.6 ?
C10 C11 H11 . . 118.6 ?
C4 C5 C6 . . 120.6(4) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
N2 C14 C13 . . 124.8(4) ?
N2 C14 H14 . . 117.6 ?
C13 C14 H14 . . 117.6 ?
S1 C7 H7A . . 109.5 ?
S1 C7 H7B . . 109.5 ?
S1 C7 H7C . . 109.5 ?
H7A C7 H7B . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C15 C18 H18A . . 109.5 ?
C15 C18 H18B . . 109.5 ?
C15 C18 H18C . . 109.5 ?
H18A C18 H18B . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C15 C16 H16 . . 119.9 ?
C17 C16 C15 . . 120.2(4) ?
C17 C16 H16 . . 119.9 ?
C13 C17 H17 . . 119.9 ?
C16 C17 C13 . . 120.1(4) ?
C16 C17 H17 . . 119.9 ?
C19 O3 H3A . . 109.5 ?
O3 C19 C20 . . 113.8(4) ?
O4 C19 O3 . . 123.8(5) ?
O4 C19 C20 . . 122.4(5) ?
C21 C20 C19 . . 123.1(5) ?
C21 C20 C25 . . 118.0(5) ?
C25 C20 C19 . . 118.9(5) ?
C20 C21 H21 . . 119.4 ?
C20 C21 C22 . . 121.1(5) ?
C22 C21 H21 . . 119.4 ?
C22 C23 H23 . . 119.8 ?
C24 C23 H23 . . 119.8 ?
C24 C23 C22 . . 120.4(5) ?
C20 C25 H25 . . 119.2 ?
C20 C25 C24 . . 121.7(5) ?
C24 C25 H25 . . 119.2 ?
C21 C22 H22 . . 120.2 ?
C23 C22 C21 . . 119.6(6) ?
C23 C22 H22 . . 120.2 ?
C23 C24 C25 . . 119.2(5) ?
C23 C24 H24 . . 120.4 ?
C25 C24 H24 . . 120.4 ?
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
Cl1 C10 . 1.733(4) ?
S1 O2 . 1.409(4) ?
S1 O1 . 1.407(4) ?
S1 C1 . 1.770(4) ?
S1 C7 . 1.712(6) ?
N1 C12 . 1.354(5) ?
N1 C11 . 1.322(5) ?
N2 C15 . 1.346(5) ?
N2 C14 . 1.328(5) ?
C12 C13 . 1.486(5) ?
C12 C8 . 1.392(5) ?
C1 C2 . 1.380(6) ?
C1 C6 . 1.357(6) ?
C13 C14 . 1.395(5) ?
C13 C17 . 1.398(5) ?
C4 C3 . 1.375(5) ?
C4 C8 . 1.505(5) ?
C4 C5 . 1.385(5) ?
C2 H2 . 0.9300 ?
C2 C3 . 1.390(6) ?
C9 H9 . 0.9300 ?
C9 C8 . 1.393(6) ?
C9 C10 . 1.373(6) ?
C3 H3 . 0.9300 ?
C10 C11 . 1.381(6) ?
C6 H6 . 0.9300 ?
C6 C5 . 1.391(6) ?
C15 C18 . 1.494(6) ?
C15 C16 . 1.379(6) ?
C11 H11 . 0.9300 ?
C5 H5 . 0.9300 ?
C14 H14 . 0.9300 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C16 H16 . 0.9300 ?
C16 C17 . 1.368(6) ?
C17 H17 . 0.9300 ?
O3 H3A . 0.8200 ?
O3 C19 . 1.302(5) ?
O4 C19 . 1.211(6) ?
C19 C20 . 1.497(6) ?
C20 C21 . 1.358(6) ?
C20 C25 . 1.372(6) ?
C21 H21 . 0.9300 ?
C21 C22 . 1.381(7) ?
C23 H23 . 0.9300 ?
C23 C22 . 1.365(7) ?
C23 C24 . 1.355(8) ?
C25 H25 . 0.9300 ?
C25 C24 . 1.375(7) ?
C22 H22 . 0.9300 ?
C24 H24 . 0.9300 ?
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
Cl1 C10 C11 N1 . . . . 176.7(3) ?
S1 C1 C2 C3 . . . . -176.8(4) ?
S1 C1 C6 C5 . . . . 175.8(4) ?
O2 S1 C1 C2 . . . . 24.4(5) ?
O2 S1 C1 C6 . . . . -153.0(5) ?
O1 S1 C1 C2 . . . . 153.5(4) ?
O1 S1 C1 C6 . . . . -23.8(5) ?
N1 C12 C13 C14 . . . . 35.2(5) ?
N1 C12 C13 C17 . . . . -145.1(4) ?
N1 C12 C8 C4 . . . . 179.7(4) ?
N1 C12 C8 C9 . . . . -2.0(6) ?
N2 C15 C16 C17 . . . . -2.0(6) ?
C12 N1 C11 C10 . . . . -0.6(7) ?
C12 C13 C14 N2 . . . . 179.6(4) ?
C12 C13 C17 C16 . . . . -179.2(4) ?
C1 C2 C3 C4 . . . . 1.1(7) ?
C1 C6 C5 C4 . . . . 0.9(8) ?
C13 C12 C8 C4 . . . . -1.5(6) ?
C13 C12 C8 C9 . . . . 176.8(4) ?
C2 C1 C6 C5 . . . . -1.5(8) ?
C9 C10 C11 N1 . . . . -2.3(7) ?
C3 C4 C8 C12 . . . . 66.2(6) ?
C3 C4 C8 C9 . . . . -112.2(5) ?
C3 C4 C5 C6 . . . . 0.6(7) ?
C8 C12 C13 C14 . . . . -143.7(4) ?
C8 C12 C13 C17 . . . . 36.0(6) ?
C8 C4 C3 C2 . . . . 175.9(4) ?
C8 C4 C5 C6 . . . . -176.9(4) ?
C8 C9 C10 Cl1 . . . . -176.0(3) ?
C8 C9 C10 C11 . . . . 2.9(6) ?
C10 C9 C8 C12 . . . . -0.9(6) ?
C10 C9 C8 C4 . . . . 177.5(4) ?
C6 C1 C2 C3 . . . . 0.5(7) ?
C15 N2 C14 C13 . . . . -1.3(6) ?
C15 C16 C17 C13 . . . . 0.5(6) ?
C11 N1 C12 C13 . . . . -176.1(4) ?
C11 N1 C12 C8 . . . . 2.8(6) ?
C5 C4 C3 C2 . . . . -1.6(7) ?
C5 C4 C8 C12 . . . . -116.3(5) ?
C5 C4 C8 C9 . . . . 65.4(6) ?
C14 N2 C15 C18 . . . . 179.8(4) ?
C14 N2 C15 C16 . . . . 2.3(6) ?
C14 C13 C17 C16 . . . . 0.5(6) ?
C7 S1 C1 C2 . . . . -91.8(5) ?
C7 S1 C1 C6 . . . . 90.8(5) ?
C18 C15 C16 C17 . . . . -179.3(4) ?
C17 C13 C14 N2 . . . . -0.2(6) ?
O3 C19 C20 C21 . . . . -2.1(7) ?
O3 C19 C20 C25 . . . . 177.0(4) ?
O4 C19 C20 C21 . . . . 177.5(5) ?
O4 C19 C20 C25 . . . . -3.4(8) ?
C19 C20 C21 C22 . . . . -179.6(5) ?
C19 C20 C25 C24 . . . . -179.9(5) ?
C20 C21 C22 C23 . . . . -0.4(9) ?
C20 C25 C24 C23 . . . . -0.7(9) ?
C21 C20 C25 C24 . . . . -0.7(8) ?
C25 C20 C21 C22 . . . . 1.2(8) ?
C22 C23 C24 C25 . . . . 1.6(9) ?
C24 C23 C22 C21 . . . . -1.0(10) ?
_cod_database_fobs_code 2312541