#------------------------------------------------------------------------------
#$Date: 2018-11-16 05:33:51 +0200 (Fri, 16 Nov 2018) $
#$Revision: 212003 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/13/2021352.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_2021352
loop_
_publ_author_name
'Rosiak, Damian'
'Okuniewski, Andrzej'
'Chojnacki, Jarosław'
_publ_section_title
;
 Copper(I) iodide ribbons coordinated with thiourea derivatives
;
_journal_coeditor_code           QF3017
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618015620
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          '[Cu Br I (C14 H11 N2 O1 S1)], 0.5C3 H6 O'
_chemical_formula_moiety         'C14 H11 Br Cu I N2 O S, 0.5(C3 H6 O)'
_chemical_formula_sum            'C15.5 H14 Br Cu I N2 O1.5 S'
_chemical_formula_weight         554.70
_chemical_name_systematic
;
Poly[[1-benzoyl-3-(4-bromophenyl)thiourea-κS]-μ₃-iodido-copper(I)]
acetone hemisolvate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                102.079(6)
_cell_angle_beta                 94.047(6)
_cell_angle_gamma                94.299(6)
_cell_formula_units_Z            2
_cell_length_a                   4.0594(3)
_cell_length_b                   10.8684(8)
_cell_length_c                   20.7336(15)
_cell_measurement_reflns_used    6948
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.46
_cell_measurement_theta_min      2.47
_cell_volume                     888.48(12)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2009)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2009)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2009)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7687
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.990
_diffrn_reflns_theta_min         2.469
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    5.339
_exptl_absorpt_correction_T_max  0.9048
_exptl_absorpt_correction_T_min  0.3583
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
[X-RED32 (Stoe & Cie, 2009), by Gaussian integration, analogous
to Coppens (1970)]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.073
_exptl_crystal_description       needle
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.022
_refine_diff_density_max         1.885
_refine_diff_density_min         -2.957
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3446
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.808
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0632
_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/[σ²(Fo²)+(0.1209P)²+2.3538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1677
_refine_ls_wR_factor_ref         0.1746
_reflns_number_gt                3069
_reflns_number_total             3446
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            qf3017sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        888.48(11)
_cod_original_formula_sum        'C15.50 H14 Br Cu I N2 O1.50 S'
_cod_database_code               2021352
_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   0.204
_shelx_estimated_absorpt_t_max   0.892
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
Cu Cu1 0.7353(2) 0.50967(9) 0.45015(4) 0.0367(3) Uani d 0.900(2) A 1
I I1 0.72245(10) 0.32964(4) 0.51899(2) 0.0331(2) Uani d 0.900(2) A 1
Br Br1 0.3217(2) -0.09639(9) 0.07159(5) 0.0580(3) Uani d 0.900(2) A 1
S S1 0.6415(5) 0.39525(19) 0.34375(9) 0.0395(4) Uani d 0.900(2) A 1
Cu Cu1A 0.785(4) 0.6685(15) 0.4747(8) 0.029(4) Uiso d 0.0453(18) B 2
I I1A 0.776(3) 0.4872(10) 0.5400(5) 0.038(3) Uiso d 0.0453(18) B 2
Br Br1A 0.338(15) 0.041(6) 0.078(3) 0.151(18) Uiso d 0.0453(18) B 2
S S1A 0.68(2) 0.558(9) 0.364(5) 0.10(2) Uiso d 0.0453(18) B 2
Cu Cu1B 0.678(5) 0.351(2) 0.4294(10) 0.060(5) Uiso d 0.0551(18) C 3
I I1B 0.666(3) 0.1721(12) 0.4984(6) 0.062(3) Uiso d 0.0551(18) C 3
Br Br1B 0.250(3) -0.2533(12) 0.0517(6) 0.038(3) Uiso d 0.0551(18) C 3
S S1B 0.583(9) 0.241(3) 0.3243(18) 0.047(8) Uiso d 0.0551(18) C 3
N N1 0.8582(17) 0.6097(6) 0.3122(3) 0.0463(14) Uani d 1 A 1
H H1 0.860628 0.638312 0.355249 0.056 Uiso calc 1 A 1
N N2 0.7669(19) 0.4367(7) 0.2243(3) 0.0522(16) Uani d 1 A 1
H H2 0.832923 0.490828 0.200671 0.063 Uiso calc 1 A 1
O O1 0.967(2) 0.6685(6) 0.2156(3) 0.0693(19) Uani d 1 A 1
C C1 0.7634(19) 0.4798(8) 0.2899(3) 0.0437(16) Uani d 1 A 1
C C16 0.8901(19) 0.8737(7) 0.3752(4) 0.0448(16) Uani d 1 A 1
H H16 0.775127 0.815977 0.396345 0.054 Uiso calc 1 A 1
C C23 0.685(2) 0.0867(9) 0.1746(4) 0.0531(19) Uani d 1 A 1
H H23 0.762630 0.015384 0.188674 0.064 Uiso calc 1 A 1
C C10 0.948(2) 0.6993(9) 0.2763(4) 0.0525(19) Uani d 1 A 1
C C15 0.944(2) 1.0023(8) 0.4061(4) 0.0466(17) Uani d 1 A 1
H H15 0.858246 1.032465 0.447361 0.056 Uiso calc 1 A 1
C C25 0.362(2) 0.1708(9) 0.0960(4) 0.057(2) Uani d 1 A 1
H H25 0.220284 0.157117 0.056229 0.068 Uiso calc 1 A 1
C C21 0.670(2) 0.3085(8) 0.1901(4) 0.0479(18) Uani d 1 A 1
C C11 1.0076(19) 0.8305(8) 0.3129(4) 0.0459(16) Uani d 1 A 1
C C22 0.786(2) 0.2072(8) 0.2109(4) 0.0485(18) Uani d 1 A 1
H H22 0.933850 0.219393 0.249789 0.058 Uiso calc 1 A 1
C C24 0.474(2) 0.0701(9) 0.1188(4) 0.0522(19) Uani d 1 A 1
C C12 1.183(2) 0.9161(8) 0.2840(4) 0.0474(17) Uani d 1 A 1
H H12 1.264643 0.887651 0.242164 0.057 Uiso calc 1 A 1
C C13 1.239(2) 1.0424(8) 0.3152(4) 0.0496(18) Uani d 1 A 1
H H13 1.360063 1.099932 0.294903 0.060 Uiso calc 1 A 1
C C14 1.120(2) 1.0847(8) 0.3762(4) 0.0484(17) Uani d 1 A 1
H H14 1.160847 1.171341 0.397616 0.058 Uiso calc 1 A 1
C C26 0.460(2) 0.2948(9) 0.1323(4) 0.056(2) Uani d 1 A 1
H H26 0.384693 0.366188 0.117945 0.067 Uiso calc 1 A 1
O O1S -0.072(7) 0.3846(16) 0.0058(12) 0.142(7) Uani d 0.5 D -1
C C2S 0.030(5) 0.4885(15) 0.0000(8) 0.120(7) Uani d 0.5 D -1
C C3S 0.060(9) 0.521(2) -0.0666(9) 0.118(8) Uani d 0.5 D -1
H H3SA -0.156737 0.502748 -0.092409 0.177 Uiso calc 0.5 D -1
H H3SB 0.221112 0.469917 -0.090205 0.177 Uiso calc 0.5 D -1
H H3SC 0.133864 0.610672 -0.060622 0.177 Uiso calc 0.5 D -1
C C1S 0.128(9) 0.5950(18) 0.0589(10) 0.120(8) Uani d 0.5 D -1
H H1SA 0.329045 0.577161 0.083131 0.180 Uiso calc 0.5 D -1
H H1SB -0.052060 0.603279 0.088163 0.180 Uiso calc 0.5 D -1
H H1SC 0.171456 0.673967 0.043958 0.180 Uiso calc 0.5 D -1
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
Cu1 Cu1 Cu1 2_766 2_666 87.58(5)
I1 Cu1 Cu1 . 2_766 56.65(3)
I1 Cu1 Cu1 2_766 2_666 120.17(5)
I1 Cu1 Cu1 2_666 2_666 56.22(3)
I1 Cu1 Cu1 2_766 2_766 56.47(3)
I1 Cu1 Cu1 2_666 2_766 120.04(5)
I1 Cu1 Cu1 . 2_666 56.62(3)
I1 Cu1 I1 . 2_766 113.12(4)
I1 Cu1 I1 . 2_666 112.84(3)
I1 Cu1 I1 2_766 2_666 99.42(3)
S1 Cu1 Cu1 . 2_666 121.97(7)
S1 Cu1 Cu1 . 2_766 127.74(8)
S1 Cu1 I1 . 2_766 117.82(6)
S1 Cu1 I1 . 2_666 112.19(7)
S1 Cu1 I1 . . 101.98(6)
Cu1 I1 Cu1 2_766 2_666 99.42(3)
Cu1 I1 Cu1 . 2_766 66.88(4)
Cu1 I1 Cu1 . 2_666 67.15(3)
C1 S1 Cu1 . . 111.3(3)
I1A Cu1A I1A 2_766 . 60.3(5)
S1A Cu1A I1A . 2_766 76(2)
S1A Cu1A I1A . . 103(2)
Cu1A I1A Cu1A 2_766 . 119.7(5)
Cu1A I1A I1A 2_766 2_766 61.3(6)
I1A I1A Cu1A 2_766 . 58.4(5)
S1B Cu1B I1B . . 102.9(13)
C1 N1 H1 . . 115.3
C10 N1 H1 . . 115.3
C10 N1 C1 . . 129.4(6)
C1 N2 H2 . . 117.7
C1 N2 C21 . . 124.6(7)
C21 N2 H2 . . 117.7
N1 C1 S1 . . 119.3(5)
N2 C1 S1 . . 125.9(6)
N2 C1 N1 . . 114.7(7)
C15 C16 H16 . . 120.1
C15 C16 C11 . . 119.7(7)
C11 C16 H16 . . 120.1
C22 C23 H23 . . 120.0
C24 C23 H23 . . 120.0
C24 C23 C22 . . 120.1(9)
N1 C10 C11 . . 116.8(7)
O1 C10 N1 . . 120.8(8)
O1 C10 C11 . . 122.3(8)
C16 C15 H15 . . 120.1
C14 C15 C16 . . 119.8(7)
C14 C15 H15 . . 120.1
C24 C25 H25 . . 120.3
C24 C25 C26 . . 119.4(8)
C26 C25 H25 . . 120.3
C22 C21 N2 . . 122.7(7)
C22 C21 C26 . . 122.2(8)
C26 C21 N2 . . 115.1(8)
C16 C11 C10 . . 123.0(7)
C12 C11 C16 . . 119.0(7)
C12 C11 C10 . . 118.0(7)
C23 C22 H22 . . 120.4
C21 C22 C23 . . 119.1(8)
C21 C22 H22 . . 120.4
C23 C24 Br1 . . 119.6(7)
C23 C24 C25 . . 121.7(9)
C25 C24 Br1 . . 118.7(7)
C11 C12 H12 . . 119.6
C13 C12 C11 . . 120.9(7)
C13 C12 H12 . . 119.6
C12 C13 H13 . . 120.0
C12 C13 C14 . . 119.9(8)
C14 C13 H13 . . 120.0
C15 C14 C13 . . 120.6(8)
C15 C14 H14 . . 119.7
C13 C14 H14 . . 119.7
C25 C26 H26 . . 121.3
C21 C26 C25 . . 117.5(9)
C21 C26 H26 . . 121.3
O1S C2S C3S . . 122.2
O1S C2S C1S . . 122.0
C1S C2S C3S . . 115.8
C2S C3S H3SA . . 109.5
C2S C3S H3SB . . 109.5
C2S C3S H3SC . . 109.5
H3SA C3S H3SB . . 109.5
H3SA C3S H3SC . . 109.5
H3SB C3S H3SC . . 109.5
C2S C1S H1SA . . 109.5
C2S C1S H1SB . . 109.5
C2S C1S H1SC . . 109.5
H1SA C1S H1SB . . 109.5
H1SA C1S H1SC . . 109.5
H1SB C1S H1SC . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 Cu1 2_766 2.9257(19)
Cu1 Cu1 2_666 2.9402(18)
Cu1 I1 2_666 2.6643(10)
Cu1 I1 . 2.6520(10)
Cu1 I1 2_766 2.6576(11)
Cu1 S1 . 2.285(2)
Br1 C24 . 1.903(9)
S1 C1 . 1.666(7)
Cu1A I1A 2_666 2.69(2)
Cu1A I1A . 2.614(18)
Cu1A I1A 2_766 2.540(19)
Cu1A S1A . 2.35(9)
I1A I1A 2_766 2.59(2)
I1A I1A 2_666 2.76(2)
Cu1B I1B . 2.64(2)
Cu1B S1B . 2.25(4)
N1 H1 . 0.8800
N1 C1 . 1.405(10)
N1 C10 . 1.388(11)
N2 H2 . 0.8800
N2 C1 . 1.343(10)
N2 C21 . 1.436(10)
O1 C10 . 1.242(10)
C16 H16 . 0.9500
C16 C15 . 1.404(11)
C16 C11 . 1.408(11)
C23 H23 . 0.9500
C23 C22 . 1.384(12)
C23 C24 . 1.362(13)
C10 C11 . 1.462(12)
C15 H15 . 0.9500
C15 C14 . 1.377(11)
C25 H25 . 0.9500
C25 C24 . 1.374(14)
C25 C26 . 1.411(13)
C21 C22 . 1.366(12)
C21 C26 . 1.398(12)
C11 C12 . 1.387(11)
C22 H22 . 0.9500
C12 H12 . 0.9500
C12 C13 . 1.384(12)
C13 H13 . 0.9500
C13 C14 . 1.386(12)
C14 H14 . 0.9500
C26 H26 . 0.9500
O1S C2S . 1.2070
C2S C3S . 1.5042
C2S C1S . 1.5040
C3S H3SA . 0.9800
C3S H3SB . 0.9800
C3S H3SC . 0.9800
C1S H1SA . 0.9800
C1S H1SB . 0.9800
C1S H1SC . 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 I1 2_766 0.88 2.95 3.688(6) 142.8 yes
N2 H2 O1 . 0.88 1.92 2.635(10) 137.2 yes
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
Cu1 S1 C1 N1 -9.1(7)
Cu1 S1 C1 N2 174.3(6)
N1 C10 C11 C16 -18.5(12)
N1 C10 C11 C12 162.6(8)
N2 C21 C22 C23 -179.0(7)
N2 C21 C26 C25 178.8(7)
O1 C10 C11 C16 159.2(9)
O1 C10 C11 C12 -19.6(13)
C1 N1 C10 O1 -2.9(15)
C1 N1 C10 C11 174.8(8)
C1 N2 C21 C22 -48.9(12)
C1 N2 C21 C26 133.6(9)
C16 C15 C14 C13 1.5(12)
C16 C11 C12 C13 -0.6(12)
C10 N1 C1 S1 -175.8(7)
C10 N1 C1 N2 1.2(12)
C10 C11 C12 C13 178.3(8)
C15 C16 C11 C10 -177.1(8)
C15 C16 C11 C12 1.7(11)
C21 N2 C1 S1 -1.2(12)
C21 N2 C1 N1 -178.1(7)
C11 C16 C15 C14 -2.2(12)
C11 C12 C13 C14 -0.1(12)
C22 C23 C24 Br1 -177.2(6)
C22 C23 C24 C25 1.5(13)
C22 C21 C26 C25 1.3(12)
C24 C23 C22 C21 0.3(12)
C24 C25 C26 C21 0.5(12)
C12 C13 C14 C15 -0.3(12)
C26 C25 C24 Br1 176.8(6)
C26 C25 C24 C23 -1.9(13)
C26 C21 C22 C23 -1.7(12)

_cod_database_fobs_code 2021352
