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#$Date: 2023-09-28 10:41:30 +0300 (Thu, 28 Sep 2023) $
#$Revision: 286577 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/75/8107566.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_8107566
loop_
_publ_author_name
'Xia, Yu-Pei'
_publ_section_title
;
 Crystal structure of
 N-(diaminomethylene)-1-(dimethylamino)-1-iminiomethanaminium dichloride,
 C4H13Cl2N5
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              799
_journal_page_last               800
_journal_paper_doi               10.1515/ncrs-2023-0218
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C4 H13 N5, 2(Cl)'
_chemical_formula_sum            'C4 H13 Cl2 N5'
_chemical_formula_weight         202.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 105.134(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1868(6)
_cell_length_b                   5.8408(4)
_cell_length_c                   12.6534(11)
_cell_measurement_reflns_used    2350
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      0.763
_cell_measurement_theta_min      0.753
_cell_volume                     512.73(7)
_computing_cell_refinement       'SAINT v6.02A (Bruker, 2001) [1]'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v6.02A (Bruker, 2001) [1]'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009) [2]'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009) [2]'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015) [3]'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015) [4]'
_diffrn_ambient_temperature      298.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3305
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.350
_diffrn_reflns_theta_min         2.974
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.46
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 919 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_coef       1.55(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         2382
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0619P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.945
_reflns_Friedel_fraction_max     0.866
_reflns_number_gt                2268
_reflns_number_total             2382
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0218_suppl_001.cif
_cod_data_source_block           h
_cod_database_code               8107566
_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_max   0.774
_shelx_estimated_absorpt_t_min   0.757
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H2d-H2b
 2.1 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N3(H3)
3.b X=CH2 refined with riding coordinates:
 N2(H2d,H2e), N4(H4a,H4b), N5(H5a,H5b)
3.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C2(H2a,H2b,H2c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.4706(5) -0.2228(6) 0.7169(3) 0.0444(7) Uani 1 1 d . . . . .
H1A H -0.415971 -0.371277 0.737610 0.067 Uiso 1 1 calc R U . . .
H1B H -0.441084 -0.175112 0.650455 0.067 Uiso 1 1 calc R U . . .
H1C H -0.607927 -0.229900 0.705353 0.067 Uiso 1 1 calc R U . . .
C2 C -0.4158(6) -0.1130(8) 0.9128(3) 0.0598(12) Uani 1 1 d . . . . .
H2A H -0.540060 -0.181902 0.904399 0.090 Uiso 1 1 calc R U . . .
H2B H -0.407448 0.024582 0.955346 0.090 Uiso 1 1 calc DR U . . .
H2C H -0.317222 -0.217948 0.949508 0.090 Uiso 1 1 calc R U . . .
C3 C -0.2648(4) 0.1060(5) 0.7946(2) 0.0303(6) Uani 1 1 d . . . . .
C4 C -0.0943(4) 0.2179(5) 0.6582(2) 0.0311(6) Uani 1 1 d . . . . .
Cl1 Cl 0.07056(11) 0.67390(13) 0.85708(6) 0.0431(3) Uani 1 1 d . . . . .
Cl2 Cl 0.33337(9) 0.30461(12) 0.55093(5) 0.0369(2) Uani 1 1 d . . . . .
N1 N -0.3892(4) -0.0572(5) 0.8045(2) 0.0365(6) Uani 1 1 d . . . . .
N2 N -0.1567(4) 0.2194(5) 0.8788(2) 0.0390(6) Uani 1 1 d . . . . .
H2D H -0.164402 0.189245 0.944057 0.047 Uiso 1 1 calc DR U . . .
H2E H -0.078514 0.323250 0.868395 0.047 Uiso 1 1 calc R U . . .
N3 N -0.2598(3) 0.1716(5) 0.69010(19) 0.0367(6) Uani 1 1 d . . . . .
H3 H -0.368037 0.184353 0.641486 0.044 Uiso 1 1 calc R U . . .
N4 N -0.1068(4) 0.3607(5) 0.5753(2) 0.0407(6) Uani 1 1 d . . . . .
H4A H -0.006283 0.390569 0.552836 0.049 Uiso 1 1 calc R U . . .
H4B H -0.215358 0.423575 0.543873 0.049 Uiso 1 1 calc R U . . .
N5 N 0.0688(4) 0.1192(5) 0.7078(2) 0.0398(6) Uani 1 1 d . . . . .
H5A H 0.171062 0.146583 0.686744 0.048 Uiso 1 1 calc R U . . .
H5B H 0.073526 0.027053 0.761466 0.048 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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'
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
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N1 C1 H1A 109.5 . .
N1 C1 H1B 109.5 . .
N1 C1 H1C 109.5 . .
H2A C2 H2B 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
N1 C2 H2A 109.5 . .
N1 C2 H2B 109.5 . .
N1 C2 H2C 109.5 . .
N1 C3 N3 118.2(2) . .
N2 C3 N1 123.3(2) . .
N2 C3 N3 118.3(3) . .
N4 C4 N3 118.1(3) . .
N5 C4 N3 120.4(3) . .
N5 C4 N4 121.6(3) . .
C2 N1 C1 115.7(3) . .
C3 N1 C1 122.9(2) . .
C3 N1 C2 120.0(3) . .
C3 N2 H2D 120.0 . .
C3 N2 H2E 120.0 . .
H2D N2 H2E 120.0 . .
C3 N3 H3 117.5 . .
C4 N3 C3 125.0(2) . .
C4 N3 H3 117.5 . .
C4 N4 H4A 120.0 . .
C4 N4 H4B 120.0 . .
H4A N4 H4B 120.0 . .
C4 N5 H5A 120.0 . .
C4 N5 H5B 120.0 . .
H5A N5 H5B 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C1 N1 1.473(4) .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
C2 N1 1.469(4) .
C3 N1 1.335(4) .
C3 N2 1.321(4) .
C3 N3 1.386(3) .
C4 N3 1.378(3) .
C4 N4 1.325(4) .
C4 N5 1.310(4) .
N2 H2D 0.8600 .
N2 H2E 0.8600 .
N3 H3 0.8600 .
N4 H4A 0.8600 .
N4 H4B 0.8600 .
N5 H5A 0.8600 .
N5 H5B 0.8600 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N1 C3 N3 C4 -139.2(3) . . . .
N2 C3 N1 C1 -163.5(3) . . . .
N2 C3 N1 C2 2.2(5) . . . .
N2 C3 N3 C4 45.6(4) . . . .
N3 C3 N1 C1 21.6(4) . . . .
N3 C3 N1 C2 -172.8(3) . . . .
N4 C4 N3 C3 -153.4(3) . . . .
N5 C4 N3 C3 27.8(5) . . . .
