#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/54/2225489.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_2225489
loop_
_publ_author_name
'Kadirova, Zukhra Ch.'
'Chepulsky, Stanislav A.'
'Parpiev, Nusrat A.'
'Talipov, Samat A.'
'Sharipov, Khasan T.'
_publ_section_title
;
 Bis(7-methoxy-1-methyl-4,9-dihydro-3H-β-carbolinium)
 tetrachloridozincate
;
_journal_coeditor_code           BV2139
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m473
_journal_paper_doi               10.1107/S1600536810010822
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '(C13 H15 N2 O)2 [Zn Cl4]'
_chemical_formula_sum            'C26 H30 Cl4 N4 O2 Zn'
_chemical_formula_weight         637.71
_chemical_name_common            'di(harmalinium) tetrachloridozincate'
_chemical_name_systematic
;
Bis(7-methoxy-1-methyl-4,9-dihydro-3H-β-carbolinium)
tetrachloridozincate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.0797(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2314(2)
_cell_length_b                   19.1274(2)
_cell_length_c                   13.5614(2)
_cell_measurement_reflns_used    4954
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.99
_cell_measurement_theta_min      4.12
_cell_volume                     2784.87(7)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       'heavy atom'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12418
_diffrn_reflns_theta_full        70.99
_diffrn_reflns_theta_max         70.99
_diffrn_reflns_theta_min         4.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.014
_exptl_absorpt_correction_T_max  0.644
_exptl_absorpt_correction_T_min  0.544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.461
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0431
_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)+(0.0588P)²+1.2361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1161
_reflns_number_gt                3724
_reflns_number_total             4954
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bv2139.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225489
_cod_database_fobs_code          2225489
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_disorder_assembly
_atom_site_disorder_group
Zn Zn1 0.76391(4) 0.05281(2) 0.78045(4) 0.04473(15) Uani d . 1 . .
Cl Cl1 0.80185(10) 0.14137(5) 0.68163(7) 0.0583(3) Uani d . 1 . .
Cl Cl2 0.90754(9) -0.03331(5) 0.80919(8) 0.0623(3) Uani d . 1 . .
Cl Cl3 0.57608(8) 0.00479(5) 0.70451(9) 0.0678(3) Uani d . 1 . .
Cl Cl4 0.77170(12) 0.10536(5) 0.93383(8) 0.0734(3) Uani d . 1 . .
O O1 0.1080(2) 0.18482(13) 0.5051(2) 0.0595(7) Uani d . 1 . .
N N1 0.0972(2) -0.04362(13) 0.6637(2) 0.0402(6) Uani d . 1 . .
H H1A 0.0414 -0.0400 0.6953 0.048 Uiso calc R 1 . .
N N2 0.2328(3) -0.21801(15) 0.6886(2) 0.0480(7) Uani d . 1 . .
H H2A 0.2367 -0.2566 0.7221 0.058 Uiso calc R 1 . .
C C1 0.1660(3) -0.10271(17) 0.6593(2) 0.0400(7) Uani d . 1 . .
C C2 0.1632(3) -0.16743(17) 0.7074(3) 0.0444(8) Uani d . 1 . .
C C3 0.3039(3) -0.21253(19) 0.6142(3) 0.0540(9) Uani d . 1 . .
H H3A 0.2531 -0.2301 0.5482 0.065 Uiso calc R 1 . .
H H3B 0.3768 -0.2423 0.6369 0.065 Uiso calc R 1 . .
C C4 0.3451(3) -0.14021(19) 0.5997(3) 0.0508(9) Uani d . 1 . .
H H4A 0.4222 -0.1300 0.6529 0.061 Uiso calc R 1 . .
H H4B 0.3613 -0.1370 0.5334 0.061 Uiso calc R 1 . .
C C5 0.2495(3) -0.08782(17) 0.6044(2) 0.0390(7) Uani d . 1 . .
C C6 0.2285(3) -0.01784(17) 0.5711(2) 0.0388(7) Uani d . 1 . .
C C7 0.2806(3) 0.02628(19) 0.5116(2) 0.0476(8) Uani d . 1 . .
H H7A 0.3440 0.0104 0.4860 0.057 Uiso calc R 1 . .
C C8 0.2367(3) 0.0920(2) 0.4926(3) 0.0521(9) Uani d . 1 . .
H H8A 0.2696 0.1214 0.4526 0.063 Uiso calc R 1 . .
C C9 0.1411(3) 0.11741(18) 0.5325(2) 0.0451(8) Uani d . 1 . .
C C10 0.0876(3) 0.07649(17) 0.5905(2) 0.0402(7) Uani d . 1 . .
H H10A 0.0247 0.0932 0.6161 0.048 Uiso calc R 1 . .
C C11 0.1329(3) 0.00793(16) 0.6094(2) 0.0357(7) Uani d . 1 . .
C C12 0.0871(4) -0.1803(2) 0.7790(3) 0.0640(11) Uani d . 1 . .
H H12A 0.0985 -0.2277 0.8032 0.096 Uiso calc R 1 . .
H H12B 0.0007 -0.1725 0.7433 0.096 Uiso calc R 1 . .
H H12C 0.1130 -0.1490 0.8367 0.096 Uiso calc R 1 . .
C C13 0.0274(4) 0.2179(2) 0.5539(3) 0.0582(10) Uani d . 1 . .
H H13A 0.0111 0.2649 0.5286 0.087 Uiso calc R 1 . .
H H13B 0.0661 0.2188 0.6271 0.087 Uiso calc R 1 . .
H H13C -0.0495 0.1925 0.5389 0.087 Uiso calc R 1 . .
N N3 0.3936(3) 0.10991(15) 0.7707(2) 0.0473(7) Uani d . 1 . .
H H3C 0.4395 0.0784 0.7550 0.057 Uiso calc R 1 . .
N N4 0.2175(3) 0.03927(17) 0.9329(2) 0.0573(8) Uani d . 1 . .
H H4C 0.2128 0.0035 0.9700 0.069 Uiso calc R 1 . .
O O2 0.4732(3) 0.32178(13) 0.5990(2) 0.0626(7) Uani d . 1 . .
C C14 0.3153(3) 0.10024(18) 0.8312(2) 0.0437(8) Uani d . 1 . .
C C15 0.3010(3) 0.03874(19) 0.8826(3) 0.0482(8) Uani d . 1 . .
C C16 0.1328(5) 0.0970(2) 0.9292(4) 0.0863(15) Uani d . 1 . .
H H16A 0.0549 0.0866 0.8771 0.104 Uiso calc R 1 . .
H H16B 0.1153 0.0994 0.9950 0.104 Uiso calc R 1 . .
C C17 0.1742(4) 0.1655(2) 0.9072(3) 0.0649(11) Uani d . 1 . .
H H17A 0.2174 0.1882 0.9717 0.078 Uiso calc R 1 . .
H H17B 0.1019 0.1937 0.8734 0.078 Uiso calc R 1 . .
C C18 0.2582(3) 0.16256(18) 0.8406(2) 0.0442(8) Uani d . 1 . .
C C19 0.3027(3) 0.21319(18) 0.7847(2) 0.0422(7) Uani d . 1 . .
C C20 0.2842(3) 0.28532(19) 0.7657(3) 0.0495(8) Uani d . 1 . .
H H20A 0.2319 0.3102 0.7949 0.059 Uiso calc R 1 . .
C C21 0.3427(3) 0.31842(18) 0.7049(3) 0.0508(9) Uani d . 1 . .
H H21A 0.3302 0.3661 0.6926 0.061 Uiso calc R 1 . .
C C22 0.4230(3) 0.28139(18) 0.6597(3) 0.0474(8) Uani d . 1 . .
C C23 0.4460(3) 0.21113(18) 0.6765(3) 0.0462(8) Uani d . 1 . .
H H23A 0.4988 0.1870 0.6470 0.055 Uiso calc R 1 . .
C C24 0.3857(3) 0.17796(17) 0.7401(2) 0.0418(7) Uani d . 1 . .
C C25 0.3748(4) -0.0254(2) 0.8814(3) 0.0622(10) Uani d . 1 . .
H H25A 0.3504 -0.0613 0.9209 0.093 Uiso calc R 1 . .
H H25B 0.4618 -0.0154 0.9108 0.093 Uiso calc R 1 . .
H H25C 0.3601 -0.0410 0.8115 0.093 Uiso calc R 1 . .
C C26 0.5400(4) 0.2872(2) 0.5392(3) 0.0639(11) Uani d . 1 . .
H H26A 0.5706 0.3211 0.5003 0.096 Uiso calc R 1 . .
H H26B 0.4858 0.2550 0.4929 0.096 Uiso calc R 1 . .
H H26C 0.6090 0.2622 0.5841 0.096 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
O O 0.0492 0.0322 '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'
Zn Zn -1.5491 0.6778 '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'
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
Cl3 Zn1 Cl2 . . 107.88(4) ?
Cl3 Zn1 Cl1 . . 110.26(4) ?
Cl2 Zn1 Cl1 . . 113.37(4) ?
Cl3 Zn1 Cl4 . . 112.03(4) ?
Cl2 Zn1 Cl4 . . 109.20(4) ?
Cl1 Zn1 Cl4 . . 104.15(4) ?
C9 O1 C13 . . 117.1(3) ?
C11 N1 C1 . . 108.2(2) ?
C2 N2 C3 . . 123.8(3) ?
N1 C1 C5 . . 109.3(3) ?
N1 C1 C2 . . 127.8(3) ?
C5 C1 C2 . . 122.8(3) ?
N2 C2 C1 . . 117.6(3) ?
N2 C2 C12 . . 119.5(3) ?
C1 C2 C12 . . 122.9(3) ?
N2 C3 C4 . . 114.3(3) ?
C5 C4 C3 . . 111.4(3) ?
C1 C5 C6 . . 106.9(3) ?
C1 C5 C4 . . 119.7(3) ?
C6 C5 C4 . . 133.0(3) ?
C7 C6 C5 . . 134.0(3) ?
C7 C6 C11 . . 119.4(3) ?
C5 C6 C11 . . 106.7(3) ?
C8 C7 C6 . . 118.6(3) ?
C7 C8 C9 . . 121.4(3) ?
O1 C9 C10 . . 124.6(3) ?
O1 C9 C8 . . 113.3(3) ?
C10 C9 C8 . . 122.1(3) ?
C9 C10 C11 . . 116.3(3) ?
N1 C11 C10 . . 128.9(3) ?
N1 C11 C6 . . 108.8(3) ?
C10 C11 C6 . . 122.2(3) ?
C24 N3 C14 . . 108.3(3) ?
C15 N4 C16 . . 123.4(3) ?
C22 O2 C26 . . 117.5(3) ?
C18 C14 N3 . . 109.5(3) ?
C18 C14 C15 . . 123.8(3) ?
N3 C14 C15 . . 126.5(3) ?
N4 C15 C14 . . 117.1(3) ?
N4 C15 C25 . . 120.0(3) ?
C14 C15 C25 . . 122.9(3) ?
C17 C16 N4 . . 116.7(4) ?
C16 C17 C18 . . 113.0(3) ?
C14 C18 C19 . . 107.3(3) ?
C14 C18 C17 . . 119.0(3) ?
C19 C18 C17 . . 133.6(3) ?
C20 C19 C18 . . 135.7(3) ?
C20 C19 C24 . . 117.8(3) ?
C18 C19 C24 . . 106.5(3) ?
C21 C20 C19 . . 119.9(3) ?
C20 C21 C22 . . 120.9(3) ?
O2 C22 C23 . . 124.2(3) ?
O2 C22 C21 . . 113.9(3) ?
C23 C22 C21 . . 121.9(3) ?
C22 C23 C24 . . 116.4(3) ?
N3 C24 C23 . . 128.5(3) ?
N3 C24 C19 . . 108.4(3) ?
C23 C24 C19 . . 123.1(3) ?
C1 N1 H1A . . 126 ?
C11 N1 H1A . . 126 ?
C2 N2 H2A . . 118 ?
C3 N2 H2A . . 118 ?
N2 C3 H3A . . 109 ?
N2 C3 H3B . . 109 ?
C4 C3 H3A . . 109 ?
C4 C3 H3B . . 109 ?
H3A C3 H3B . . 108 ?
C3 C4 H4A . . 109 ?
C3 C4 H4B . . 109 ?
C5 C4 H4A . . 109 ?
C5 C4 H4B . . 109 ?
H4A C4 H4B . . 108 ?
C6 C7 H7A . . 121 ?
C8 C7 H7A . . 121 ?
C7 C8 H8A . . 119 ?
C9 C8 H8A . . 119 ?
C9 C10 H10A . . 122 ?
C11 C10 H10A . . 122 ?
C2 C12 H12A . . 110 ?
C2 C12 H12B . . 109 ?
C2 C12 H12C . . 109 ?
H12A C12 H12B . . 109 ?
H12A C12 H12C . . 109 ?
H12B C12 H12C . . 109 ?
O1 C13 H13A . . 109 ?
O1 C13 H13B . . 109 ?
O1 C13 H13C . . 109 ?
H13A C13 H13B . . 109 ?
H13A C13 H13C . . 109 ?
H13B C13 H13C . . 110 ?
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
Zn1 Cl3 . 2.2536(10) ?
Zn1 Cl2 . 2.2580(10) ?
Zn1 Cl1 . 2.2765(9) ?
Zn1 Cl4 . 2.2885(10) ?
O1 C9 . 1.363(4) ?
O1 C13 . 1.417(4) ?
N1 C11 . 1.359(4) ?
N1 C1 . 1.380(4) ?
N2 C2 . 1.315(4) ?
N2 C3 . 1.463(4) ?
C1 C5 . 1.388(4) ?
C1 C2 . 1.404(4) ?
C2 C12 . 1.491(5) ?
C3 C4 . 1.490(5) ?
C4 C5 . 1.484(4) ?
C5 C6 . 1.410(5) ?
C6 C7 . 1.407(4) ?
C6 C11 . 1.412(4) ?
C7 C8 . 1.348(5) ?
C8 C9 . 1.422(5) ?
C9 C10 . 1.367(4) ?
C10 C11 . 1.403(4) ?
N3 C24 . 1.361(4) ?
N3 C14 . 1.381(4) ?
N4 C15 . 1.312(5) ?
N4 C16 . 1.450(5) ?
O2 C22 . 1.365(4) ?
O2 C26 . 1.420(4) ?
C14 C18 . 1.377(5) ?
C14 C15 . 1.400(5) ?
C15 C25 . 1.484(5) ?
C16 C17 . 1.449(6) ?
C17 C18 . 1.487(5) ?
C18 C19 . 1.409(5) ?
C19 C20 . 1.407(5) ?
C19 C24 . 1.422(4) ?
C20 C21 . 1.353(5) ?
C21 C22 . 1.420(5) ?
C22 C23 . 1.375(5) ?
C23 C24 . 1.396(5) ?
N1 H1A . 0.86 ?
N2 H2A . 0.86 ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
C7 H7A . 0.93 ?
C8 H8A . 0.93 ?
C10 H10A . 0.93 ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?
C13 H13A . 0.96 ?
C13 H13B . 0.96 ?
C13 H13C . 0.96 ?
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 H1A Cl2 1_455 0.86 2.45 3.307(3) 171 yes
N2 H2A Cl1 2_646 0.86 2.46 3.299(3) 166 yes
N3 H3C Cl3 . 0.86 2.33 3.183(3) 173 yes
N4 H4C Cl4 3_657 0.86 2.44 3.287(3) 170 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 O1 C9 C8 . . . . -170.7(3) n
C13 O1 C9 C10 . . . . 10.7(4) n
C11 N1 C1 C2 . . . . 177.5(3) n
C11 N1 C1 C5 . . . . 2.0(3) n
C1 N1 C11 C6 . . . . -1.3(3) n
C1 N1 C11 C10 . . . . 178.6(3) n
C3 N2 C2 C1 . . . . -5.5(5) n
C3 N2 C2 C12 . . . . 175.5(3) n
C2 N2 C3 C4 . . . . 29.2(5) n
N1 C1 C2 N2 . . . . 176.8(3) n
N1 C1 C2 C12 . . . . -4.2(6) n
C5 C1 C2 N2 . . . . -8.3(5) n
C5 C1 C2 C12 . . . . 170.7(3) n
N1 C1 C5 C4 . . . . 172.5(3) n
N1 C1 C5 C6 . . . . -1.9(3) n
C2 C1 C5 C4 . . . . -3.3(5) n
C2 C1 C5 C6 . . . . -177.7(3) n
N2 C3 C4 C5 . . . . -36.8(4) n
C3 C4 C5 C1 . . . . 25.9(4) n
C3 C4 C5 C6 . . . . -161.5(3) n
C1 C5 C6 C7 . . . . -178.5(3) n
C1 C5 C6 C11 . . . . 1.1(3) n
C4 C5 C6 C7 . . . . 8.2(6) n
C4 C5 C6 C11 . . . . -172.2(3) n
C5 C6 C7 C8 . . . . 179.2(3) n
C11 C6 C7 C8 . . . . -0.4(4) n
C5 C6 C11 N1 . . . . 0.1(3) n
C5 C6 C11 C10 . . . . -179.83 n
C7 C6 C11 N1 . . . . 179.8(3) n
C7 C6 C11 C10 . . . . -0.2(4) n
C6 C7 C8 C9 . . . . 0.9(5) n
C7 C8 C9 O1 . . . . -179.7(3) n
C7 C8 C9 C10 . . . . -1.1(5) n
O1 C9 C10 C11 . . . . 179.0(3) n
C8 C9 C10 C11 . . . . 0.5(4) n
C9 C10 C11 N1 . . . . -179.8(3) n
C9 C10 C11 C6 . . . . 0.1(4) n
