#------------------------------------------------------------------------------
#$Date: 2020-03-11 08:36:20 +0200 (Wed, 11 Mar 2020) $
#$Revision: 249272 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/33/2243313.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_2243313
loop_
_publ_author_name
'Moon, Dohyun'
'Choi, Jong-Ha'
_publ_section_title
;
 Crystal structure of
 1,4,8,11-tetramethyl-1,4,8,11-tetraazoniacyclotetradecane
 bis[chloridochromate(VI)] dichloride from synchrotron X-ray data
;
_journal_coeditor_code           VM2229
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              523
_journal_page_last               526
_journal_paper_doi               10.1107/S2056989020003059
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          '(C14 H36 N4) [Cr O3 Cl]2 Cl2'
_chemical_formula_moiety         'C14 H36 N4 4+, 2(Cr O3 Cl -), 2(Cl -)'
_chemical_formula_sum            'C14 H36 Cl4 Cr2 N4 O6'
_chemical_formula_weight         602.27
_chemical_name_systematic
;
1,4,8,11-Tetramethyl-1,4,8,11-tetraazoniacyclotetradecane
bis[chloridochromate(VI)] dichloride
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                77.61(3)
_cell_angle_beta                 88.20(3)
_cell_angle_gamma                79.39(3)
_cell_formula_units_Z            1
_cell_length_a                   7.0610(14)
_cell_length_b                   8.6740(17)
_cell_length_c                   10.775(2)
_cell_measurement_reflns_used    41622
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      33.679
_cell_measurement_theta_min      0.350
_cell_volume                     633.5(2)
_computing_cell_refinement
;
HKL3000sm (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
PAL BL2D-SMDC (Shin et al., 2016)
;
_computing_data_reduction
;
HKL3000sm (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics
;
DIAMOND4 (Putz & Brandenburg, 2014)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.610
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6933
_diffrn_reflns_theta_full        21.469
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         1.661
_diffrn_source                   'PLSII 2D bending magnet'
_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.552
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
(HKL3000sm Scalepack; Otwinowski & Minor, 1997)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.111
_refine_diff_density_max         0.814
_refine_diff_density_min         -1.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         3503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1021P)²+0.4428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1496
_reflns_number_gt                3357
_reflns_number_total             3503
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm2229sup1.cif
_cod_data_source_block           I
_cod_database_code               2243313
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.839
_shelx_estimated_absorpt_t_max   0.911
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.5951(2) 0.43908(19) 0.24944(14) 0.0197(3) Uani d 1 . .
H H1 0.655924 0.528759 0.203398 0.024 Uiso calc 1 . .
N N2 0.3111(2) 0.75634(17) 0.10259(15) 0.0178(3) Uani d 1 . .
H H2 0.448197 0.736710 0.077822 0.021 Uiso calc 1 . .
C C1 0.8079(3) 0.1708(2) 0.01696(18) 0.0203(3) Uani d 1 . .
H H1A 0.942223 0.140900 -0.007767 0.024 Uiso calc 1 . .
H H1AB 0.763915 0.071671 0.058488 0.024 Uiso calc 1 . .
C C2 0.8030(2) 0.2755(2) 0.11389(17) 0.0202(3) Uani d 1 . .
H H2A 0.850838 0.373545 0.074404 0.024 Uiso calc 1 . .
H H2AB 0.889395 0.217967 0.184918 0.024 Uiso calc 1 . .
C C3 0.6013(3) 0.3211(2) 0.16488(18) 0.0216(3) Uani d 1 . .
H H3A 0.511705 0.368064 0.093415 0.026 Uiso calc 1 . .
H H3AB 0.559012 0.224125 0.212911 0.026 Uiso calc 1 . .
C C4 0.7083(4) 0.3635(3) 0.3696(2) 0.0350(5) Uani d 1 . .
H H4A 0.710246 0.443738 0.419628 0.052 Uiso calc 1 . .
H H4B 0.839127 0.320257 0.348638 0.052 Uiso calc 1 . .
H H4C 0.648561 0.277582 0.418098 0.052 Uiso calc 1 . .
C C5 0.3917(3) 0.5084(2) 0.28166(17) 0.0214(3) Uani d 1 . .
H H5A 0.398383 0.581772 0.338417 0.026 Uiso calc 1 . .
H H5AB 0.331618 0.420559 0.329015 0.026 Uiso calc 1 . .
C C6 0.2612(2) 0.5985(2) 0.16973(17) 0.0191(3) Uani d 1 . .
H H6A 0.265642 0.529620 0.108100 0.023 Uiso calc 1 . .
H H6AB 0.128516 0.617792 0.200171 0.023 Uiso calc 1 . .
C C7 0.2870(3) 0.8760(2) 0.1871(2) 0.0287(4) Uani d 1 . .
H H7A 0.309296 0.978749 0.138299 0.043 Uiso calc 1 . .
H H7B 0.378911 0.838265 0.256843 0.043 Uiso calc 1 . .
H H7C 0.157143 0.888100 0.220467 0.043 Uiso calc 1 . .
Cr Cr1 0.20005(5) 0.19152(4) 0.58525(3) 0.02581(14) Uani d 1 . .
Cl Cl1 0.21038(11) 0.11680(9) 0.40216(7) 0.04726(19) Uani d 1 . .
O O1 0.2178(4) 0.0382(3) 0.6983(2) 0.0578(6) Uani d 1 . .
O O2 0.0005(3) 0.3102(3) 0.59266(19) 0.0461(5) Uani d 1 . .
O O3 0.3790(3) 0.2812(3) 0.5855(2) 0.0459(5) Uani d 1 . .
Cl Cl2 0.74460(6) 0.71108(6) 0.05475(5) 0.02599(15) Uani d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0019 0.0011 '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 0.0040 0.0024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0074 0.0043 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1166 0.1176 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cr Cr 0.2796 0.4720 '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
C4 N1 C3 . . 110.93(15) ?
C4 N1 C5 . . 109.63(15) ?
C3 N1 C5 . . 112.58(14) ?
C4 N1 H1 . . 107.8 ?
C3 N1 H1 . . 107.8 ?
C5 N1 H1 . . 107.8 ?
C6 N2 C7 . . 112.00(15) ?
C6 N2 C1 . 2_665 112.21(14) ?
C7 N2 C1 . 2_665 108.81(14) ?
C6 N2 H2 . . 107.9 ?
C7 N2 H2 . . 107.9 ?
C1 N2 H2 2_665 . 107.9 ?
N2 C1 C2 2_665 . 116.39(14) ?
N2 C1 H1A 2_665 . 108.2 ?
C2 C1 H1A . . 108.2 ?
N2 C1 H1AB 2_665 . 108.2 ?
C2 C1 H1AB . . 108.2 ?
H1A C1 H1AB . . 107.3 ?
C1 C2 C3 . . 112.61(15) ?
C1 C2 H2A . . 109.1 ?
C3 C2 H2A . . 109.1 ?
C1 C2 H2AB . . 109.1 ?
C3 C2 H2AB . . 109.1 ?
H2A C2 H2AB . . 107.8 ?
N1 C3 C2 . . 111.86(15) ?
N1 C3 H3A . . 109.2 ?
C2 C3 H3A . . 109.2 ?
N1 C3 H3AB . . 109.2 ?
C2 C3 H3AB . . 109.2 ?
H3A C3 H3AB . . 107.9 ?
N1 C4 H4A . . 109.5 ?
N1 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
N1 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N1 C5 C6 . . 116.12(14) ?
N1 C5 H5A . . 108.3 ?
C6 C5 H5A . . 108.3 ?
N1 C5 H5AB . . 108.3 ?
C6 C5 H5AB . . 108.3 ?
H5A C5 H5AB . . 107.4 ?
N2 C6 C5 . . 115.04(15) ?
N2 C6 H6A . . 108.5 ?
C5 C6 H6A . . 108.5 ?
N2 C6 H6AB . . 108.5 ?
C5 C6 H6AB . . 108.5 ?
H6A C6 H6AB . . 107.5 ?
N2 C7 H7A . . 109.5 ?
N2 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
N2 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O1 Cr1 O2 . . 110.49(14) ?
O1 Cr1 O3 . . 111.05(14) ?
O2 Cr1 O3 . . 111.22(13) ?
O1 Cr1 Cl1 . . 109.69(10) ?
O2 Cr1 Cl1 . . 108.34(8) ?
O3 Cr1 Cl1 . . 105.90(9) ?
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
N1 C4 . 1.501(2) ?
N1 C3 . 1.503(2) ?
N1 C5 . 1.511(2) ?
N1 H1 . 0.9900 ?
N2 C6 . 1.503(2) ?
N2 C7 . 1.505(2) ?
N2 C1 2_665 1.513(2) ?
N2 H2 . 0.9900 ?
C1 C2 . 1.520(3) ?
C1 H1A . 0.9800 ?
C1 H1AB . 0.9800 ?
C2 C3 . 1.524(2) ?
C2 H2A . 0.9800 ?
C2 H2AB . 0.9800 ?
C3 H3A . 0.9800 ?
C3 H3AB . 0.9800 ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C4 H4C . 0.9700 ?
C5 C6 . 1.521(3) ?
C5 H5A . 0.9800 ?
C5 H5AB . 0.9800 ?
C6 H6A . 0.9800 ?
C6 H6AB . 0.9800 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C7 H7C . 0.9700 ?
Cr1 O1 . 1.588(2) ?
Cr1 O2 . 1.596(2) ?
Cr1 O3 . 1.602(2) ?
Cr1 Cl1 . 2.2000(9) ?
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 H1 Cl2 . 0.99 2.16 3.120(2) 162.6 yes
N2 H2 Cl2 . 0.99 2.08 3.0553(17) 169.6 yes
C2 H2A Cl2 . 0.98 2.85 3.642(2) 138.6 yes
C4 H4C O3 . 0.97 2.58 3.299(4) 130.9 yes
C5 H5AB Cl1 . 0.98 2.86 3.804(2) 161.4 yes
C3 H3A Cl2 2_665 0.98 2.72 3.541(2) 141.5 yes
C1 H1A Cl2 2_765 0.98 2.74 3.511(2) 136.3 yes
C1 H1AB O1 2_656 0.98 2.59 3.230(3) 123.2 yes
C2 H2AB O1 2_656 0.98 2.54 3.047(3) 112.1 yes
C3 H3AB O1 2_656 0.98 2.53 3.193(3) 124.6 yes
C4 H4A O3 2_666 0.97 2.34 3.168(3) 142.6 yes
C5 H5A O3 2_666 0.98 2.40 3.218(3) 141.0 yes
C7 H7B O3 2_666 0.97 2.38 3.343(3) 172.7 yes
C4 H4B Cl1 1_655 0.97 2.88 3.773(3) 154.1 yes
C6 H6AB O2 2_566 0.98 2.54 3.260(3) 130.1 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
N2 C1 C2 C3 2_665 . . . 61.3(2) ?
C4 N1 C3 C2 . . . . -67.1(2) ?
C5 N1 C3 C2 . . . . 169.64(15) ?
C1 C2 C3 N1 . . . . -173.71(14) ?
C4 N1 C5 C6 . . . . 176.52(17) ?
C3 N1 C5 C6 . . . . -59.5(2) ?
C7 N2 C6 C5 . . . . -64.42(19) ?
C1 N2 C6 C5 2_665 . . . 172.85(14) ?
N1 C5 C6 N2 . . . . -69.9(2) ?

_cod_database_fobs_code 2243313
