#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/26/8102695.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_8102695
loop_
_publ_author_name
'Chun-Yan Liu'
'Fu-An Sun'
'Ming-Yang He'
_publ_section_title
;
 Crystal structure of
 1,1,3,3-tetramethyl-2-(1,3-dimethylimidazolidin-2-yl)guanidinium
 chloride, (C10H24N5)Cl
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              327
_journal_volume                  225
_journal_year                    2010
_chemical_formula_moiety         'C10 H24 N5, Cl'
_chemical_formula_sum            'C10 H24 Cl N5'
_chemical_formula_weight         249.79
_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                 97.634(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0491(16)
_cell_length_b                   6.7268(9)
_cell_length_c                   16.947(2)
_cell_measurement_reflns_used    3621
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.31
_cell_measurement_theta_min      2.22
_cell_volume                     1361.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.1829
_diffrn_reflns_av_sigmaI/netI    0.1189
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7893
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.9688
_exptl_absorpt_correction_T_min  0.9292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.031(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0671
_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)+(0.0954P)²+0.2798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1870
_refine_ls_wR_factor_ref         0.2027
_reflns_number_gt                2072
_reflns_number_total             2675
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2964.cff
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               8102695
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.72180(17) 0.2203(3) 0.54329(12) 0.0297(5) Uani 1 1 d . . .
C2 C 0.92935(19) 0.2159(4) 0.56916(17) 0.0466(6) Uani 1 1 d . . .
H2A H 0.9168 0.0896 0.5928 0.070 Uiso 1 1 calc R . .
H2B H 0.9671 0.3030 0.6089 0.070 Uiso 1 1 calc R . .
H2C H 0.9747 0.1976 0.5272 0.070 Uiso 1 1 calc R . .
C3 C 0.8308(2) 0.4782(4) 0.48686(17) 0.0514(7) Uani 1 1 d . . .
H3A H 0.8615 0.4401 0.4396 0.077 Uiso 1 1 calc R . .
H3B H 0.8792 0.5739 0.5160 0.077 Uiso 1 1 calc R . .
H3C H 0.7581 0.5357 0.4723 0.077 Uiso 1 1 calc R . .
C4 C 0.7735(2) 0.1711(5) 0.68788(14) 0.0508(7) Uani 1 1 d . . .
H4A H 0.8254 0.0658 0.7039 0.076 Uiso 1 1 calc R . .
H4B H 0.7232 0.1866 0.7269 0.076 Uiso 1 1 calc R . .
H4C H 0.8139 0.2928 0.6835 0.076 Uiso 1 1 calc R . .
C5 C 0.6200(2) -0.0214(4) 0.61266(17) 0.0566(7) Uani 1 1 d . . .
H5A H 0.5667 0.0288 0.6451 0.085 Uiso 1 1 calc R . .
H5B H 0.6507 -0.1442 0.6347 0.085 Uiso 1 1 calc R . .
H5C H 0.5833 -0.0440 0.5596 0.085 Uiso 1 1 calc R . .
C6 C 0.63966(16) 0.2405(3) 0.41102(13) 0.0292(5) Uani 1 1 d . . .
H6 H 0.7031 0.3328 0.4179 0.035 Uiso 1 1 calc R . .
C7 C 0.6826(2) 0.1582(4) 0.28604(13) 0.0419(6) Uani 1 1 d . . .
H7A H 0.6642 0.0400 0.2542 0.050 Uiso 1 1 calc R . .
H7B H 0.7499 0.2180 0.2708 0.050 Uiso 1 1 calc R . .
C8 C 0.5859(2) 0.3047(4) 0.27745(14) 0.0449(6) Uani 1 1 d . . .
H8A H 0.6013 0.4179 0.2452 0.054 Uiso 1 1 calc R . .
H8B H 0.5168 0.2419 0.2540 0.054 Uiso 1 1 calc R . .
C9 C 0.5065(2) 0.5193(4) 0.38030(16) 0.0517(7) Uani 1 1 d . . .
H9A H 0.4321 0.4675 0.3792 0.078 Uiso 1 1 calc R . .
H9B H 0.5058 0.6264 0.3428 0.078 Uiso 1 1 calc R . .
H9C H 0.5328 0.5675 0.4328 0.078 Uiso 1 1 calc R . .
C10 C 0.7707(3) -0.0425(4) 0.40416(17) 0.0545(7) Uani 1 1 d . . .
H10A H 0.8466 -0.0039 0.4009 0.082 Uiso 1 1 calc R . .
H10B H 0.7540 -0.1631 0.3746 0.082 Uiso 1 1 calc R . .
H10C H 0.7611 -0.0639 0.4589 0.082 Uiso 1 1 calc R . .
Cl1 Cl 0.48752(7) 0.78948(11) 0.18027(5) 0.0657(3) Uani 1 1 d . . .
N1 N 0.63231(14) 0.2431(3) 0.48840(11) 0.0342(5) Uani 1 1 d . . .
H1 H 0.5708 0.2944 0.4994 0.051 Uiso 1 1 d R . .
N2 N 0.82131(15) 0.3038(3) 0.53629(12) 0.0361(5) Uani 1 1 d . . .
N3 N 0.70943(16) 0.1225(3) 0.61063(11) 0.0376(5) Uani 1 1 d . . .
N5 N 0.58020(16) 0.3634(3) 0.35944(11) 0.0409(5) Uani 1 1 d . . .
N6 N 0.69594(16) 0.1125(3) 0.37126(11) 0.0378(5) Uani 1 1 d . . .
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'
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
_geom_angle_publ_flag
N1 C1 N3 118.54(19) . . ?
N1 C1 N2 122.51(19) . . ?
N3 C1 N2 118.76(19) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 N6 127.89(19) . . ?
N1 C6 N5 122.45(19) . . ?
N6 C6 N5 109.43(19) . . ?
N1 C6 H6 91.6 . . ?
N6 C6 H6 91.6 . . ?
N5 C6 H6 91.6 . . ?
N6 C7 C8 102.31(18) . . ?
N6 C7 H7A 111.3 . . ?
C8 C7 H7A 111.3 . . ?
N6 C7 H7B 111.3 . . ?
C8 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
N5 C8 C7 102.57(19) . . ?
N5 C8 H8A 111.3 . . ?
C7 C8 H8A 111.3 . . ?
N5 C8 H8B 111.3 . . ?
C7 C8 H8B 111.3 . . ?
H8A C8 H8B 109.2 . . ?
N5 C9 H9A 109.5 . . ?
N5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N6 C10 H10A 109.5 . . ?
N6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 N1 C1 122.22(18) . . ?
C6 N1 H1 113.1 . . ?
C1 N1 H1 122.3 . . ?
C1 N2 C3 121.85(19) . . ?
C1 N2 C2 123.63(19) . . ?
C3 N2 C2 114.13(19) . . ?
C1 N3 C5 120.87(19) . . ?
C1 N3 C4 123.0(2) . . ?
C5 N3 C4 115.6(2) . . ?
C6 N5 C9 125.45(19) . . ?
C6 N5 C8 111.50(19) . . ?
C9 N5 C8 122.55(19) . . ?
C6 N6 C10 127.3(2) . . ?
C6 N6 C7 111.50(18) . . ?
C10 N6 C7 121.0(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.336(3) . ?
C1 N3 1.342(3) . ?
C1 N2 1.344(3) . ?
C2 N2 1.471(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 N2 1.455(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 N3 1.466(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 N3 1.453(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N1 1.326(3) . ?
C6 N6 1.333(3) . ?
C6 N5 1.340(3) . ?
C6 H6 0.9800 . ?
C7 N6 1.464(3) . ?
C7 C8 1.518(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N5 1.455(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N5 1.448(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N6 1.441(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N1 H1 0.8603 . ?
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
_geom_torsion_publ_flag
N6 C7 C8 N5 15.6(3) . . . . ?
N6 C6 N1 C1 45.6(3) . . . . ?
N5 C6 N1 C1 -140.6(2) . . . . ?
N3 C1 N1 C6 -145.0(2) . . . . ?
N2 C1 N1 C6 40.1(3) . . . . ?
N1 C1 N2 C3 23.0(3) . . . . ?
N3 C1 N2 C3 -151.9(2) . . . . ?
N1 C1 N2 C2 -149.4(2) . . . . ?
N3 C1 N2 C2 35.7(3) . . . . ?
N1 C1 N3 C5 24.8(3) . . . . ?
N2 C1 N3 C5 -160.1(2) . . . . ?
N1 C1 N3 C4 -146.8(2) . . . . ?
N2 C1 N3 C4 28.3(3) . . . . ?
N1 C6 N5 C9 3.6(4) . . . . ?
N6 C6 N5 C9 178.4(2) . . . . ?
N1 C6 N5 C8 -168.5(2) . . . . ?
N6 C6 N5 C8 6.4(3) . . . . ?
C7 C8 N5 C6 -14.3(3) . . . . ?
C7 C8 N5 C9 173.4(2) . . . . ?
N1 C6 N6 C10 -6.3(4) . . . . ?
N5 C6 N6 C10 179.2(2) . . . . ?
N1 C6 N6 C7 179.5(2) . . . . ?
N5 C6 N6 C7 5.0(3) . . . . ?
C8 C7 N6 C6 -13.4(3) . . . . ?
C8 C7 N6 C10 172.0(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9359342
