#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:52:06 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180402 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/71/7207190.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_7207190
loop_
_publ_author_name
'Su, Chien-Cheng'
'Lee, Kwang-Ming'
_publ_section_title
;
 Ionic liquid crystal engineering of 3-carbamoyl-1-alkylpyridin-1-ium
 tetrachlorocuprate(II) and tetrachlorozincate(II) salts
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              1283
_journal_paper_doi               10.1039/c1ce06160g
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C36 H62 Cl4 Cu N4 O2'
_chemical_formula_weight         788.25
_chemical_name_systematic
;
?
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 106.286(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.8976(4)
_cell_length_b                   36.792(2)
_cell_length_c                   8.2696(5)
_cell_measurement_reflns_used    4336
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.2195
_cell_measurement_theta_min      2.7948
_cell_volume                     2014.4(2)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19202
_diffrn_reflns_theta_full        26.45
_diffrn_reflns_theta_max         26.45
_diffrn_reflns_theta_min         1.11
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.8975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Columnar
_exptl_crystal_F_000             838
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.975
_refine_diff_density_rms         0.151
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0641P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.1287
_reflns_number_gt                3200
_reflns_number_total             4218
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce06160g.txt
_cod_data_source_block           110443lt_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               7207190
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu 0.47366(7) 0.2500 0.06054(6) 0.01231(16) Uani 1 2 d S
Cl1 Cl 0.42699(10) 0.30738(2) 0.13454(9) 0.01586(19) Uani 1 1 d .
Cl2 Cl 0.82120(14) 0.2500 0.15687(13) 0.0156(2) Uani 1 2 d S
Cl3 Cl 0.28338(15) 0.2500 -0.20541(13) 0.0173(2) Uani 1 2 d S
O1 O 1.2777(3) 0.15066(6) 0.6009(3) 0.0218(5) Uani 1 1 d .
N2 N 1.1424(4) 0.19189(7) 0.3996(3) 0.0181(6) Uani 1 1 d .
H2A H 1.2366 0.1886 0.3480 0.022 Uiso 1 1 calc R
H2B H 1.0448 0.2077 0.3598 0.022 Uiso 1 1 calc R
N1 N 0.8664(3) 0.17048(7) 0.8600(3) 0.0123(5) Uani 1 1 d .
C1 C 1.1476(4) 0.17298(9) 0.5380(4) 0.0145(7) Uani 1 1 d .
C2 C 0.9796(4) 0.18011(8) 0.6180(4) 0.0117(6) Uani 1 1 d .
C3 C 1.0074(4) 0.16623(8) 0.7774(4) 0.0126(6) Uani 1 1 d .
H3 H 1.1283 0.1534 0.8299 0.015 Uiso 1 1 calc R
C4 C 0.8995(4) 0.15335(9) 1.0291(4) 0.0161(7) Uani 1 1 d .
H4A H 0.8213 0.1667 1.0936 0.019 Uiso 1 1 calc R
H4B H 1.0443 0.1550 1.0918 0.019 Uiso 1 1 calc R
C5 C 0.8349(4) 0.11367(8) 1.0136(4) 0.0154(7) Uani 1 1 d .
H5A H 0.8700 0.1028 1.1276 0.018 Uiso 1 1 calc R
H5B H 0.9126 0.1006 0.9476 0.018 Uiso 1 1 calc R
C6 C 0.6100(4) 0.10783(8) 0.9300(4) 0.0154(7) Uani 1 1 d .
H6A H 0.5316 0.1227 0.9892 0.018 Uiso 1 1 calc R
H6B H 0.5771 0.1165 0.8119 0.018 Uiso 1 1 calc R
C7 C 0.5451(4) 0.06834(8) 0.9308(4) 0.0150(7) Uani 1 1 d .
H7A H 0.5724 0.0600 1.0489 0.018 Uiso 1 1 calc R
H7B H 0.6270 0.0533 0.8756 0.018 Uiso 1 1 calc R
C8 C 0.3223(4) 0.06269(8) 0.8408(4) 0.0163(7) Uani 1 1 d .
H8A H 0.2957 0.0708 0.7225 0.020 Uiso 1 1 calc R
H8B H 0.2408 0.0781 0.8952 0.020 Uiso 1 1 calc R
C9 C 0.2538(4) 0.02321(8) 0.8422(4) 0.0165(7) Uani 1 1 d .
H9A H 0.3382 0.0077 0.7912 0.020 Uiso 1 1 calc R
H9B H 0.2762 0.0153 0.9605 0.020 Uiso 1 1 calc R
C10 C 0.0318(4) 0.01739(8) 0.7471(4) 0.0174(7) Uani 1 1 d .
H10A H -0.0522 0.0333 0.7969 0.021 Uiso 1 1 calc R
H10B H 0.0101 0.0250 0.6285 0.021 Uiso 1 1 calc R
C11 C -0.0394(4) -0.02180(8) 0.7501(4) 0.0168(7) Uani 1 1 d .
H11A H 0.0439 -0.0377 0.6998 0.020 Uiso 1 1 calc R
H11B H -0.0182 -0.0294 0.8685 0.020 Uiso 1 1 calc R
C12 C -0.2613(4) -0.02689(8) 0.6545(4) 0.0171(7) Uani 1 1 d .
H12A H -0.2811 -0.0194 0.5360 0.021 Uiso 1 1 calc R
H12B H -0.3433 -0.0105 0.7039 0.021 Uiso 1 1 calc R
C13 C -0.3404(4) -0.06559(8) 0.6559(4) 0.0168(7) Uani 1 1 d .
H13A H -0.2628 -0.0821 0.6027 0.020 Uiso 1 1 calc R
H13B H -0.3191 -0.0736 0.7739 0.020 Uiso 1 1 calc R
C14 C -0.5637(4) -0.06840(9) 0.5626(4) 0.0189(7) Uani 1 1 d .
H14A H -0.5837 -0.0608 0.4441 0.023 Uiso 1 1 calc R
H14B H -0.6400 -0.0513 0.6142 0.023 Uiso 1 1 calc R
C15 C -0.6498(5) -0.10653(9) 0.5645(5) 0.0268(8) Uani 1 1 d .
H15A H -0.5810 -0.1234 0.5071 0.040 Uiso 1 1 calc R
H15B H -0.7946 -0.1063 0.5063 0.040 Uiso 1 1 calc R
H15C H -0.6290 -0.1144 0.6813 0.040 Uiso 1 1 calc R
C16 C 0.8012(4) 0.19870(8) 0.5424(4) 0.0144(6) Uani 1 1 d .
H16 H 0.7778 0.2083 0.4319 0.017 Uiso 1 1 calc R
C17 C 0.6582(4) 0.20302(8) 0.6301(4) 0.0156(7) Uani 1 1 d .
H17 H 0.5363 0.2158 0.5805 0.019 Uiso 1 1 calc R
C18 C 0.6938(4) 0.18872(8) 0.7890(4) 0.0151(6) Uani 1 1 d .
H18 H 0.5963 0.1917 0.8494 0.018 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 0.0033 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'
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'
Cl Cl 0.1484 0.1585 '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'
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
Cl3 Cu1 Cl1 100.35(2) . 4_565
Cl3 Cu1 Cl1 100.35(2) . .
Cl1 Cu1 Cl1 140.05(4) 4_565 .
Cl3 Cu1 Cl2 127.62(4) . .
Cl1 Cu1 Cl2 96.92(2) 4_565 .
Cl1 Cu1 Cl2 96.92(2) . .
C1 N2 H2A 120.0 . .
C1 N2 H2B 120.0 . .
H2A N2 H2B 120.0 . .
C3 N1 C18 120.8(3) . .
C3 N1 C4 119.0(2) . .
C18 N1 C4 120.1(2) . .
O1 C1 N2 123.9(3) . .
O1 C1 C2 119.5(3) . .
N2 C1 C2 116.5(3) . .
C3 C2 C16 118.8(3) . .
C3 C2 C1 115.9(3) . .
C16 C2 C1 125.3(3) . .
N1 C3 C2 121.1(3) . .
N1 C3 H3 119.4 . .
C2 C3 H3 119.4 . .
N1 C4 C5 111.3(2) . .
N1 C4 H4A 109.4 . .
C5 C4 H4A 109.4 . .
N1 C4 H4B 109.4 . .
C5 C4 H4B 109.4 . .
H4A C4 H4B 108.0 . .
C4 C5 C6 114.2(2) . .
C4 C5 H5A 108.7 . .
C6 C5 H5A 108.7 . .
C4 C5 H5B 108.7 . .
C6 C5 H5B 108.7 . .
H5A C5 H5B 107.6 . .
C7 C6 C5 113.3(2) . .
C7 C6 H6A 108.9 . .
C5 C6 H6A 108.9 . .
C7 C6 H6B 108.9 . .
C5 C6 H6B 108.9 . .
H6A C6 H6B 107.7 . .
C6 C7 C8 112.7(2) . .
C6 C7 H7A 109.1 . .
C8 C7 H7A 109.1 . .
C6 C7 H7B 109.1 . .
C8 C7 H7B 109.1 . .
H7A C7 H7B 107.8 . .
C7 C8 C9 113.4(3) . .
C7 C8 H8A 108.9 . .
C9 C8 H8A 108.9 . .
C7 C8 H8B 108.9 . .
C9 C8 H8B 108.9 . .
H8A C8 H8B 107.7 . .
C10 C9 C8 113.4(3) . .
C10 C9 H9A 108.9 . .
C8 C9 H9A 108.9 . .
C10 C9 H9B 108.9 . .
C8 C9 H9B 108.9 . .
H9A C9 H9B 107.7 . .
C11 C10 C9 113.9(3) . .
C11 C10 H10A 108.8 . .
C9 C10 H10A 108.8 . .
C11 C10 H10B 108.8 . .
C9 C10 H10B 108.8 . .
H10A C10 H10B 107.7 . .
C12 C11 C10 112.9(3) . .
C12 C11 H11A 109.0 . .
C10 C11 H11A 109.0 . .
C12 C11 H11B 109.0 . .
C10 C11 H11B 109.0 . .
H11A C11 H11B 107.8 . .
C11 C12 C13 114.8(3) . .
C11 C12 H12A 108.6 . .
C13 C12 H12A 108.6 . .
C11 C12 H12B 108.6 . .
C13 C12 H12B 108.6 . .
H12A C12 H12B 107.5 . .
C14 C13 C12 111.9(3) . .
C14 C13 H13A 109.2 . .
C12 C13 H13A 109.2 . .
C14 C13 H13B 109.2 . .
C12 C13 H13B 109.2 . .
H13A C13 H13B 107.9 . .
C13 C14 C15 113.5(3) . .
C13 C14 H14A 108.9 . .
C15 C14 H14A 108.9 . .
C13 C14 H14B 108.9 . .
C15 C14 H14B 108.9 . .
H14A C14 H14B 107.7 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C17 C16 C2 119.3(3) . .
C17 C16 H16 120.4 . .
C2 C16 H16 120.4 . .
C18 C17 C16 119.6(3) . .
C18 C17 H17 120.2 . .
C16 C17 H17 120.2 . .
N1 C18 C17 120.4(3) . .
N1 C18 H18 119.8 . .
C17 C18 H18 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Cl3 2.2227(12) .
Cu1 Cl1 2.2459(7) 4_565
Cu1 Cl1 2.2461(7) .
Cu1 Cl2 2.3044(11) .
O1 C1 1.220(3) .
N2 C1 1.331(4) .
N2 H2A 0.8800 .
N2 H2B 0.8800 .
N1 C3 1.345(3) .
N1 C18 1.349(4) .
N1 C4 1.492(4) .
C1 C2 1.510(4) .
C2 C3 1.375(4) .
C2 C16 1.393(4) .
C3 H3 0.9500 .
C4 C5 1.521(4) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.526(4) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.521(4) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.522(4) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.528(4) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.528(4) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.526(4) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.525(4) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.526(4) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.521(4) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.525(4) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C17 1.388(4) .
C16 H16 0.9500 .
C17 C18 1.372(4) .
C17 H17 0.9500 .
C18 H18 0.9500 .
