#------------------------------------------------------------------------------
#$Date: 2016-03-03 04:58:15 +0200 (Thu, 03 Mar 2016) $
#$Revision: 177152 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/15/2241587.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_2241587
loop_
_publ_author_name
'Jiang, Zhi-Hao'
'Zhao, Jian-Ping'
'Ma, Xiu-Ming'
'Bai, Sheng-Di'
_publ_section_title
;
 Crystal structure of bis(N-tert-butylbenzamidinium)
 hexachloridozirconate(IV) dichloromethane disolvate
;
_journal_coeditor_code           XU5884
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              432
_journal_page_last               435
_journal_paper_doi               10.1107/S2056989016003030
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          '(C11 H17 N2) [Zr Cl6], 2C H2 Cl2'
_chemical_formula_moiety         '2(C11 H17 N2 +), Cl6 Zr 2-, 2(C H2 Cl2)'
_chemical_formula_sum            'C24 H38 Cl10 N4 Zr'
_chemical_formula_weight         828.30
_chemical_name_systematic
;
Bis(N-tert-butylbenzamidinium)
hexachloridozirconate(IV) dichloromethane disolvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.259(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.443(5)
_cell_length_b                   16.154(9)
_cell_length_c                   10.891(6)
_cell_measurement_reflns_used    2094
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.945
_cell_measurement_theta_min      2.256
_cell_volume                     1836.8(17)
_computing_cell_refinement
;
SAINT (Bruker, 2000)
;
_computing_data_collection
;
SMART (Bruker, 2000)
;
_computing_data_reduction
;
SAINT (Bruker, 2000)
;
_computing_molecular_graphics
;
SHELXTL/PC (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART area-detector'
_diffrn_measurement_method       'φ and ω scan'
_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  0.0614
_diffrn_reflns_av_sigmaI/netI    0.0676
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10309
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    1.048
_exptl_absorpt_correction_T_max  0.8586
_exptl_absorpt_correction_T_min  0.8177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.731
_refine_diff_density_min         -0.897
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3410
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0714
_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)+(0.1176P)²+2.8350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1839
_refine_ls_wR_factor_ref         0.2132
_reflns_number_gt                2255
_reflns_number_total             3410
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            xu5884sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1836.9(17)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2241587
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Zr Zr1 1.0000 0.0000 0.5000 0.0430(3) Uani d S 1 2
Cl Cl1 0.79402(15) 0.05446(10) 0.41944(16) 0.0611(5) Uani d . 1 1
Cl Cl2 1.08156(15) 0.14274(9) 0.52270(16) 0.0589(5) Uani d . 1 1
Cl Cl3 0.91663(19) 0.00651(11) 0.70660(16) 0.0667(5) Uani d . 1 1
N N1 0.7169(5) 0.7997(3) 0.7141(5) 0.0614(15) Uani d . 1 1
H H1 0.7742 0.8232 0.6673 0.074 Uiso calc R 1 1
N N2 0.6913(6) 0.7035(4) 0.8664(6) 0.0803(19) Uani d . 1 1
H H2A 0.6097 0.7159 0.8731 0.096 Uiso calc R 1 1
H H2B 0.7259 0.6649 0.9135 0.096 Uiso calc R 1 1
C C1 0.5840(7) 0.8317(4) 0.6987(8) 0.0678(19) Uani d . 1 1
C C2 0.5393(11) 0.8666(7) 0.8189(11) 0.116(4) Uani d . 1 1
H H2C 0.5848 0.8390 0.8871 0.175 Uiso calc R 1 1
H H2D 0.4470 0.8573 0.8258 0.175 Uiso calc R 1 1
H H2E 0.5571 0.9261 0.8219 0.175 Uiso calc R 1 1
C C3 0.5923(8) 0.9014(6) 0.6076(10) 0.097(3) Uani d . 1 1
H H3A 0.6571 0.9413 0.6360 0.145 Uiso calc R 1 1
H H3B 0.5089 0.9290 0.6000 0.145 Uiso calc R 1 1
H H3C 0.6161 0.8793 0.5275 0.145 Uiso calc R 1 1
C C4 0.4977(8) 0.7642(6) 0.6490(11) 0.105(3) Uani d . 1 1
H H4A 0.5305 0.7441 0.5708 0.157 Uiso calc R 1 1
H H4B 0.4110 0.7862 0.6360 0.157 Uiso calc R 1 1
H H4C 0.4954 0.7184 0.7079 0.157 Uiso calc R 1 1
C C5 0.7605(6) 0.7420(4) 0.7870(7) 0.0595(17) Uani d . 1 1
C C6 0.8982(7) 0.7194(4) 0.7806(7) 0.0614(17) Uani d . 1 1
C C7 0.9913(7) 0.7784(5) 0.7678(7) 0.070(2) Uani d . 1 1
H H7 0.9687 0.8353 0.7640 0.084 Uiso calc R 1 1
C C8 1.1165(8) 0.7553(6) 0.7606(8) 0.084(2) Uani d . 1 1
H H8 1.1813 0.7962 0.7540 0.100 Uiso calc R 1 1
C C9 1.1485(9) 0.6735(6) 0.7630(9) 0.095(3) Uani d . 1 1
H H9 1.2358 0.6577 0.7575 0.113 Uiso calc R 1 1
C C10 1.0578(9) 0.6150(6) 0.7731(11) 0.105(3) Uani d . 1 1
H H10 1.0814 0.5582 0.7733 0.127 Uiso calc R 1 1
C C11 0.9321(9) 0.6364(5) 0.7831(9) 0.092(3) Uani d . 1 1
H H11 0.8684 0.5949 0.7916 0.110 Uiso calc R 1 1
C C12 0.335(2) 0.4738(14) 0.5569(19) 0.248(13) Uani d . 1 1
H H12A 0.4220 0.4533 0.5391 0.298 Uiso calc R 1 1
H H12B 0.3246 0.4692 0.6468 0.298 Uiso calc R 1 1
Cl Cl4 0.2363(6) 0.4119(4) 0.4939(5) 0.232(3) Uani d . 1 1
Cl Cl5 0.3316(6) 0.5793(3) 0.5205(4) 0.1913(19) Uani 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 0.0000 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -2.9673 0.5597 '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
Cl3 Zr1 Cl3 3_756 . 180.0000(10)
Cl3 Zr1 Cl1 3_756 . 90.77(7)
Cl3 Zr1 Cl1 . . 89.23(7)
Cl3 Zr1 Cl1 3_756 3_756 89.23(7)
Cl3 Zr1 Cl1 . 3_756 90.77(7)
Cl1 Zr1 Cl1 . 3_756 180.00(8)
Cl3 Zr1 Cl2 3_756 3_756 89.81(6)
Cl3 Zr1 Cl2 . 3_756 90.19(6)
Cl1 Zr1 Cl2 . 3_756 90.07(6)
Cl1 Zr1 Cl2 3_756 3_756 89.93(6)
Cl3 Zr1 Cl2 3_756 . 90.19(6)
Cl3 Zr1 Cl2 . . 89.81(6)
Cl1 Zr1 Cl2 . . 89.93(6)
Cl1 Zr1 Cl2 3_756 . 90.07(6)
Cl2 Zr1 Cl2 3_756 . 180.00(8)
C5 N1 C1 . . 129.1(6)
C5 N1 H1 . . 115.4
C1 N1 H1 . . 115.4
C5 N2 H2A . . 120.0
C5 N2 H2B . . 120.0
H2A N2 H2B . . 120.0
N1 C1 C3 . . 105.5(6)
N1 C1 C4 . . 109.8(6)
C3 C1 C4 . . 110.3(8)
N1 C1 C2 . . 109.7(7)
C3 C1 C2 . . 108.4(8)
C4 C1 C2 . . 112.8(8)
C1 C2 H2C . . 109.5
C1 C2 H2D . . 109.5
H2C C2 H2D . . 109.5
C1 C2 H2E . . 109.5
H2C C2 H2E . . 109.5
H2D C2 H2E . . 109.5
C1 C3 H3A . . 109.5
C1 C3 H3B . . 109.5
H3A C3 H3B . . 109.5
C1 C3 H3C . . 109.5
H3A C3 H3C . . 109.5
H3B C3 H3C . . 109.5
C1 C4 H4A . . 109.5
C1 C4 H4B . . 109.5
H4A C4 H4B . . 109.5
C1 C4 H4C . . 109.5
H4A C4 H4C . . 109.5
H4B C4 H4C . . 109.5
N2 C5 N1 . . 123.9(6)
N2 C5 C6 . . 117.8(6)
N1 C5 C6 . . 118.3(6)
C7 C6 C11 . . 119.5(7)
C7 C6 C5 . . 121.5(6)
C11 C6 C5 . . 118.9(7)
C8 C7 C6 . . 119.9(7)
C8 C7 H7 . . 120.1
C6 C7 H7 . . 120.1
C7 C8 C9 . . 120.0(8)
C7 C8 H8 . . 120.0
C9 C8 H8 . . 120.0
C10 C9 C8 . . 120.6(9)
C10 C9 H9 . . 119.7
C8 C9 H9 . . 119.7
C9 C10 C11 . . 120.6(9)
C9 C10 H10 . . 119.7
C11 C10 H10 . . 119.7
C10 C11 C6 . . 119.3(9)
C10 C11 H11 . . 120.4
C6 C11 H11 . . 120.4
Cl4 C12 Cl5 . . 120.5(12)
Cl4 C12 H12A . . 107.2
Cl5 C12 H12A . . 107.2
Cl4 C12 H12B . . 107.2
Cl5 C12 H12B . . 107.2
H12A C12 H12B . . 106.8
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
Zr1 Cl1 . 2.4674(18) y
Zr1 Cl1 3_756 2.4674(18) ?
Zr1 Cl2 3_756 2.4687(19) ?
Zr1 Cl2 . 2.4687(19) y
Zr1 Cl3 3_756 2.433(2) ?
Zr1 Cl3 . 2.433(2) y
N1 C5 . 1.300(8) ?
N1 C1 . 1.487(9) ?
N1 H1 . 0.8800 ?
N2 C5 . 1.299(9) ?
N2 H2A . 0.8800 ?
N2 H2B . 0.8800 ?
C1 C3 . 1.505(11) ?
C1 C4 . 1.508(12) ?
C1 C2 . 1.509(13) ?
C2 H2C . 0.9800 ?
C2 H2D . 0.9800 ?
C2 H2E . 0.9800 ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C3 H3C . 0.9800 ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C4 H4C . 0.9800 ?
C5 C6 . 1.487(10) ?
C6 C7 . 1.371(10) ?
C6 C11 . 1.387(10) ?
C7 C8 . 1.363(11) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.364(12) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.345(13) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.365(13) ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
C12 Cl4 . 1.583(17) ?
C12 Cl5 . 1.75(2) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
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
N1 H1 Cl2 3_766 0.88 2.64 3.491(6) 162
N2 H2A Cl2 2_656 0.88 2.60 3.270(7) 133
N2 H2B Cl1 2_656 0.88 2.56 3.353(7) 150
C12 H12A Cl5 3_666 0.99 2.72 3.70(2) 171

_cod_database_fobs_code 2241587
