Crystal structure of N-(diaminomethylene)-1-(dimethylamino)-1-iminiomethanaminium dichloride, C4H13Cl2N5
Xia, Yu-Pei; Zeitschrift für Kristallographie - New Crystal Structures 238 (2023) 799–800; doi:10.1515/ncrs-2023-0218

data_8107566
_publ_section_title
;
 Crystal structure of
 N-(diaminomethylene)-1-(dimethylamino)-1-iminiomethanaminium dichloride,
 C4H13Cl2N5
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur 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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0619P)^2^] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0218_suppl_001.cif
_cod_data_source_block           h
_cod_database_code               8107566
_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'