#------------------------------------------------------------------------------
#$Date: 2017-08-31 16:49:38 +0300 (Thu, 31 Aug 2017) $
#$Revision: 200043 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/08/2020876.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_2020876
loop_
_publ_author_name
'Kelley, Annette'
'Nalla, Sowjanya'
'Bond, Marcus R.'
_publ_section_title
;
 The square-planar to flattened-tetrahedral CuX42−(X= Cl, Br)
 structural phase transition in 1,2,6-trimethylpyridinium salts
;
_journal_coeditor_code           OG5072
_journal_issue                   1
_journal_name_full
'Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials'
_journal_page_first              48
_journal_page_last               60
_journal_paper_doi               10.1107/S205252061402664X
_journal_volume                  71
_journal_year                    2015
_chemical_formula_moiety         '2(C9 H14 N1 1+), (C14 Cu1 2-)'
_chemical_formula_sum            'C18 H28 Cl4 Cu N2'
_chemical_formula_weight         477.76
_chemical_name_systematic
;
bis(methyl(2-phenylethyl)ammonium tetrachloridocuprate(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 116.3140(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.42340(10)
_cell_length_b                   22.4819(4)
_cell_length_c                   8.45520(10)
_cell_measurement_reflns_used    3915
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.03
_cell_measurement_theta_min      1
_cell_volume                     1094.49(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3814
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        32.03
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         3.24
_exptl_absorpt_coefficient_mu    1.49
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.45
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             494
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.507
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     171
_refine_ls_number_reflns         3814
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0234
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0207P)²+0.1059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.055
_refine_ls_wR_factor_ref         0.0572
_reflns_number_gt                3186
_reflns_number_total             3814
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            og5072sup1_nmphcucl4.cif
_cod_data_source_block           nmphcucl4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2020876
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0 0 0 0.01156(5) Uani d S 1 2 . .
Cl Cl1 -0.22895(4) -0.042521(11) 0.10657(3) 0.01423(6) Uani d . 1 1 . .
Cl Cl2 0.10995(4) 0.071176(13) 0.21497(4) 0.01842(7) Uani d . 1 1 . .
C C1 0.3837(2) 0.27495(6) 0.13980(16) 0.0210(2) Uani d . 1 1 . .
H H1 0.237(3) 0.2550(6) 0.0950(19) 0.025(4) Uiso d . 1 1 . .
C C2 0.3916(2) 0.33518(6) 0.17589(16) 0.0245(3) Uani d . 1 1 . .
H H2 0.256(3) 0.3559(8) 0.157(2) 0.038(4) Uiso d . 1 1 . .
C C3 0.6017(2) 0.36514(6) 0.24559(16) 0.0233(3) Uani d . 1 1 . .
H H3 0.606(3) 0.4046(7) 0.274(2) 0.031(4) Uiso d . 1 1 . .
C C4 0.8038(2) 0.33486(6) 0.27757(16) 0.0227(2) Uani d . 1 1 . .
H H4 0.945(3) 0.3540(8) 0.329(2) 0.036(4) Uiso d . 1 1 . .
C C5 0.7958(2) 0.27460(5) 0.23977(15) 0.0191(2) Uani d . 1 1 . .
H H5 0.931(3) 0.2539(7) 0.260(2) 0.025(4) Uiso d . 1 1 . .
C C6 0.58655(19) 0.24371(5) 0.17151(14) 0.0159(2) Uani d . 1 1 . .
C C7 0.5811(2) 0.17769(5) 0.13885(15) 0.0194(2) Uani d . 1 1 . .
H H7A 0.425(3) 0.1656(6) 0.0577(19) 0.025(4) Uiso d . 1 1 . .
H H7B 0.681(2) 0.1673(6) 0.0894(19) 0.023(4) Uiso d . 1 1 . .
C C8 0.65191(19) 0.14323(5) 0.30936(14) 0.0147(2) Uani d . 1 1 . .
H H8A 0.547(2) 0.1494(6) 0.3587(18) 0.016(3) Uiso d . 1 1 . .
H H8B 0.805(2) 0.1538(6) 0.3945(18) 0.018(3) Uiso d . 1 1 . .
N N9 0.65539(16) 0.07808(4) 0.27732(12) 0.01320(17) Uani d . 1 1 . .
H H9A 0.523(3) 0.0694(6) 0.1929(19) 0.020(4) Uiso d . 1 1 . .
H H9B 0.764(3) 0.0706(6) 0.2383(18) 0.021(4) Uiso d . 1 1 . .
C C10 0.7111(2) 0.04144(5) 0.43702(15) 0.0172(2) Uani d . 1 1 . .
H H10A 0.598(2) 0.0473(6) 0.4812(18) 0.015(3) Uiso d . 1 1 . .
H H10B 0.858(3) 0.0539(6) 0.5284(19) 0.021(4) Uiso d . 1 1 . .
H H10C 0.707(3) 0.0019(7) 0.406(2) 0.023(4) Uiso d . 1 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 0 '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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
Cl1 Cu1 Cl2 . . 90.309(9)
C6 C1 C2 . . 120.63(11)
C6 C1 H1 . . 120.8(9)
C2 C1 H1 . . 118.6(9)
C1 C2 C3 . . 120.22(12)
C1 C2 H2 . . 120.5(10)
C3 C2 H2 . . 119.3(10)
C2 C3 C4 . . 119.83(12)
C2 C3 H3 . . 119.5(10)
C4 C3 H3 . . 120.6(10)
C3 C4 C5 . . 120.00(12)
C3 C4 H4 . . 120.5(10)
C5 C4 H4 . . 119.4(11)
C4 C5 C6 . . 120.89(11)
C4 C5 H5 . . 120.6(9)
C6 C5 H5 . . 118.6(9)
C5 C6 C1 . . 118.43(11)
C5 C6 C7 . . 120.50(11)
C1 C6 C7 . . 121.04(11)
C6 C7 C8 . . 110.84(9)
C6 C7 H7A . . 109.7(9)
C8 C7 H7A . . 108.0(9)
C6 C7 H7B . . 111.2(9)
C8 C7 H7B . . 108.7(9)
H7A C7 H7B . . 108.3(12)
C7 C8 N9 . . 110.55(9)
C7 C8 H8A . . 111.8(8)
N9 C8 H8A . . 107.2(8)
C7 C8 H8B . . 111.3(8)
N9 C8 H8B . . 106.7(8)
H8A C8 H8B . . 109.1(11)
C8 N9 C10 . . 113.39(9)
C8 N9 H9A . . 106.7(10)
C10 N9 H9A . . 112.5(10)
C8 N9 H9B . . 108.8(9)
C10 N9 H9B . . 108.2(9)
H9A N9 H9B . . 107.0(13)
N9 C10 H10A . . 111.0(8)
N9 C10 H10B . . 109.0(8)
H10A C10 H10B . . 106.9(11)
N9 C10 H10C . . 108.3(10)
H10A C10 H10C . . 108.0(12)
H10B C10 H10C . . 113.7(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 Cl1 . 2.2502(2)
Cu1 Cl2 . 2.2858(3)
C6 C1 . 1.3974(16)
C1 C2 . 1.3840(18)
C1 H1 . 0.960(15)
C2 C3 . 1.3845(19)
C2 H2 . 0.938(17)
C3 C4 . 1.3822(19)
C3 H3 . 0.917(16)
C4 C5 . 1.3878(18)
C4 H4 . 0.921(17)
C5 C6 . 1.3906(16)
C5 H5 . 0.930(15)
C6 C7 . 1.5074(16)
C7 C8 . 1.5179(16)
C7 H7A . 0.971(15)
C7 H7B . 0.936(14)
C8 N9 . 1.4914(15)
C8 H8A . 0.947(13)
C8 H8B . 0.956(14)
N9 C10 . 1.4838(14)
N9 H9A . 0.855(15)
N9 H9B . 0.912(14)
C10 H10A . 0.960(13)
C10 H10B . 0.960(15)
C10 H10C . 0.924(15)
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
N9 H9A Cl1 3 0.855(13) 2.471(13) 3.2860(10) 159.6(14) yes
N9 H9A Cl2 . 0.855(13) 2.744(19) 3.3070(10) 124.9(14) yes
N9 H9B Cl2 1_655 0.912(19) 2.314(18) 3.1930(10) 161.7(15) yes
N9 H9B Cl1 1_655 0.912(19) 2.785(15) 3.3070(10) 117.6(11) yes

_cod_database_fobs_code 2020876
