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#$Date: 2016-03-23 16:46:31 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179393 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/90/4329015.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_4329015
loop_
_publ_author_name
'Peter De Vreese'
'Neil R. Brooks'
'Kristof Van Hecke'
'Luc Van Meervelt'
'Edward Matthijs'
'Koen Binnemans'
'Rik Van Deun'
_publ_contact_author_address
;Katholieke Universiteit Leuven 
Department of chemistry 
Laboratory of coordination chemistry 
Celestijnenlaan 200f, bus 2404 
B-3001 Leuven (Belgium) 
;
_publ_contact_author_email       koen.binnemans@chem.kuleuven.be
_publ_contact_author_fax         '+32 16 32 79 92'
_publ_contact_author_name        'Koen Binnemans'
_publ_contact_author_phone       '+32 16 32 74 46'
_publ_section_title
;
 Speciation of Copper(II) Complexes in an Ionic Liquid Based on Choline
 Chloride and in Choline Chloride/Water Mixtures
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4972
_journal_page_last               4981
_journal_paper_doi               10.1021/ic202341m
_journal_volume                  51
_journal_year                    2012
_chemical_formula_moiety         'C5 H14 Cl3 Cu N O'
_chemical_formula_sum            'C5 H14 Cl3 Cu N O'
_chemical_formula_weight         274.06
_chemical_name_common
; 
 choline copper trichloride 
;
_chemical_name_systematic
; 
 choline copper trichloride 
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.829(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9847(4)
_cell_length_b                   7.8230(4)
_cell_length_c                   16.5567(7)
_cell_measurement_reflns_used    2928
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.122
_cell_measurement_theta_min      5.344
_cell_volume                     1034.09(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SAINT'
_computing_data_reduction        'Bruker SMART'
_computing_publication_material
; 
A.L.Spek (2010) PLATON, A Multipurpose Crystallographic Tool, Utrecht University
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SMART 6000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'crossed G\"obel mirrors'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13501
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         71.03
_diffrn_reflns_theta_min         5.34
_exptl_absorpt_coefficient_mu    9.719
_exptl_absorpt_correction_T_max  0.2467
_exptl_absorpt_correction_T_min  0.1122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(17)
_refine_ls_extinction_coef       0.0065(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3900
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0255P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0749
_reflns_number_gt                3715
_reflns_number_total             3900
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic202341m_si_001.cif
_cod_data_source_block           kb19
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               4329015
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu 0.53177(7) 0.23507(7) 0.14141(3) 0.02863(15) Uani 1 1 d .
Cl1 Cl 0.58738(12) 0.00110(11) 0.06387(6) 0.0345(2) Uani 1 1 d .
Cl2 Cl 0.71790(11) 0.15836(11) 0.24014(5) 0.0317(2) Uani 1 1 d .
Cl3 Cl 0.35034(13) 0.34379(12) 0.04869(5) 0.0384(2) Uani 1 1 d .
O1 O 0.4686(4) 0.4411(3) 0.21217(15) 0.0274(5) Uani 1 1 d .
H1A H 0.370(8) 0.436(6) 0.219(3) 0.029(12) Uiso 1 1 d .
C2 C 0.5130(5) 0.6139(4) 0.1908(2) 0.0293(8) Uani 1 1 d .
H2A H 0.4181 0.6910 0.2026 0.035 Uiso 1 1 calc R
H2B H 0.5345 0.6198 0.1321 0.035 Uiso 1 1 calc R
C3 C 0.6649(5) 0.6729(4) 0.2364(2) 0.0257(7) Uani 1 1 d .
H3A H 0.6989 0.7850 0.2143 0.031 Uiso 1 1 calc R
H3B H 0.7569 0.5913 0.2259 0.031 Uiso 1 1 calc R
N4 N 0.6481(4) 0.6913(4) 0.32756(17) 0.0254(6) Uani 1 1 d .
C5 C 0.8040(6) 0.7760(6) 0.3584(3) 0.0442(10) Uani 1 1 d .
H5A H 0.8183 0.8860 0.3311 0.066 Uiso 1 1 calc R
H5B H 0.9007 0.7027 0.3478 0.066 Uiso 1 1 calc R
H5C H 0.7953 0.7950 0.4167 0.066 Uiso 1 1 calc R
C6 C 0.6334(7) 0.5210(5) 0.3682(2) 0.0421(10) Uani 1 1 d .
H6A H 0.6200 0.5378 0.4264 0.063 Uiso 1 1 calc R
H6B H 0.7349 0.4539 0.3587 0.063 Uiso 1 1 calc R
H6C H 0.5358 0.4599 0.3462 0.063 Uiso 1 1 calc R
C7 C 0.5022(6) 0.8003(6) 0.3480(3) 0.0455(11) Uani 1 1 d .
H7A H 0.5022 0.8215 0.4064 0.068 Uiso 1 1 calc R
H7B H 0.3984 0.7418 0.3320 0.068 Uiso 1 1 calc R
H7C H 0.5099 0.9094 0.3192 0.068 Uiso 1 1 calc R
Cu2 Cu 1.03583(7) 0.25817(6) 0.15796(3) 0.02837(15) Uani 1 1 d .
Cl4 Cl 1.09334(12) 0.49126(11) 0.23665(5) 0.0330(2) Uani 1 1 d .
Cl5 Cl 0.85741(13) 0.40451(11) 0.07518(6) 0.0364(2) Uani 1 1 d .
Cl6 Cl 1.23110(12) 0.09853(11) 0.22355(5) 0.0327(2) Uani 1 1 d .
O8 O 0.9636(4) 0.0487(3) 0.09150(14) 0.0265(5) Uani 1 1 d .
H8A H 0.857(7) 0.060(6) 0.088(3) 0.028(11) Uiso 1 1 d .
C9 C 0.9995(5) -0.1312(4) 0.1042(2) 0.0278(7) Uani 1 1 d .
H9A H 0.9017 -0.1998 0.0860 0.033 Uiso 1 1 calc R
H9B H 1.0172 -0.1523 0.1626 0.033 Uiso 1 1 calc R
C10 C 1.1502(5) -0.1876(4) 0.05976(18) 0.0253(7) Uani 1 1 d .
H10A H 1.1737 -0.3079 0.0746 0.030 Uiso 1 1 calc R
H10B H 1.2467 -0.1183 0.0788 0.030 Uiso 1 1 calc R
N11 N 1.1409(4) -0.1759(4) -0.03229(15) 0.0246(6) Uani 1 1 d .
C12 C 1.1565(7) 0.0050(5) -0.0595(2) 0.0411(10) Uani 1 1 d .
H12A H 1.1591 0.0088 -0.1186 0.062 Uiso 1 1 calc R
H12B H 1.2603 0.0542 -0.0372 0.062 Uiso 1 1 calc R
H12C H 1.0605 0.0710 -0.0404 0.062 Uiso 1 1 calc R
C13 C 1.2891(8) -0.2688(7) -0.0646(3) 0.0546(14) Uani 1 1 d .
H13A H 1.2837 -0.3893 -0.0487 0.082 Uiso 1 1 calc R
H13B H 1.3921 -0.2177 -0.0425 0.082 Uiso 1 1 calc R
H13C H 1.2889 -0.2603 -0.1236 0.082 Uiso 1 1 calc R
C14 C 0.9832(8) -0.2501(7) -0.0643(3) 0.0574(14) Uani 1 1 d .
H14A H 0.8882 -0.1825 -0.0454 0.086 Uiso 1 1 calc R
H14B H 0.9724 -0.3682 -0.0453 0.086 Uiso 1 1 calc R
H14C H 0.9846 -0.2489 -0.1235 0.086 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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
O1 Cu1 Cl3 86.10(8) . .
O1 Cu1 Cl2 87.74(8) . .
Cl3 Cu1 Cl2 173.13(4) . .
O1 Cu1 Cl1 176.87(10) . .
Cl3 Cu1 Cl1 92.73(4) . .
Cl2 Cu1 Cl1 93.57(4) . .
O1 Cu1 Cl6 79.33(9) . 1_455
Cl3 Cu1 Cl6 86.11(4) . 1_455
Cl2 Cu1 Cl6 95.74(3) . 1_455
Cl1 Cu1 Cl6 97.70(4) . 1_455
O1 Cu1 Cl5 94.56(9) . .
Cl3 Cu1 Cl5 97.48(4) . .
Cl2 Cu1 Cl5 79.98(3) . .
Cl1 Cu1 Cl5 88.47(4) . .
Cl6 Cu1 Cl5 172.74(3) 1_455 .
Cu1 Cl2 Cu2 98.85(3) . .
C2 O1 Cu1 122.0(2) . .
O1 C2 C3 111.5(3) . .
C2 C3 N4 116.6(3) . .
C7 N4 C5 108.6(3) . .
C7 N4 C6 109.9(4) . .
C5 N4 C6 108.1(3) . .
C7 N4 C3 111.1(3) . .
C5 N4 C3 107.2(3) . .
C6 N4 C3 111.7(3) . .
O8 Cu2 Cl6 90.17(8) . .
O8 Cu2 Cl5 84.84(8) . .
Cl6 Cu2 Cl5 171.58(5) . .
O8 Cu2 Cl4 174.98(9) . .
Cl6 Cu2 Cl4 92.03(4) . .
Cl5 Cu2 Cl4 93.50(4) . .
O8 Cu2 Cl2 78.59(8) . .
Cl6 Cu2 Cl2 102.73(4) . .
Cl5 Cu2 Cl2 82.96(4) . .
Cl4 Cu2 Cl2 96.52(4) . .
O8 Cu2 Cl3 94.65(8) . 1_655
Cl6 Cu2 Cl3 81.10(3) . 1_655
Cl5 Cu2 Cl3 92.53(4) . 1_655
Cl4 Cu2 Cl3 90.14(4) . 1_655
Cl2 Cu2 Cl3 172.15(3) . 1_655
Cu2 Cl5 Cu1 95.28(4) . .
C9 O8 Cu2 130.1(2) . .
O8 C9 C10 112.1(3) . .
C9 C10 N11 116.6(3) . .
C14 N11 C12 109.8(4) . .
C14 N11 C13 110.8(4) . .
C12 N11 C13 106.5(4) . .
C14 N11 C10 111.3(3) . .
C12 N11 C10 110.8(3) . .
C13 N11 C10 107.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 2.060(3) .
Cu1 Cl3 2.2614(10) .
Cu1 Cl2 2.2739(9) .
Cu1 Cl1 2.2830(10) .
Cu1 Cl6 2.9747(12) 1_455
Cu1 Cl5 3.1309(13) .
Cl2 Cu2 3.0009(12) .
O1 C2 1.443(4) .
C2 C3 1.493(5) .
C3 N4 1.523(4) .
N4 C7 1.487(5) .
N4 C5 1.494(5) .
N4 C6 1.498(5) .
Cu2 O8 2.052(2) .
Cu2 Cl6 2.2630(10) .
Cu2 Cl5 2.2720(10) .
Cu2 Cl4 2.2838(9) .
Cu2 Cl3 3.1873(13) 1_655
O8 C9 1.450(4) .
C9 C10 1.487(5) .
C10 N11 1.527(4) .
N11 C14 1.477(6) .
N11 C12 1.491(5) .
N11 C13 1.494(6) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A Cl4 0.79(6) 2.28(6) 3.054(3) 166(5) 1_455
O8 H8A Cl1 0.86(6) 2.23(6) 3.055(3) 161(4) .
