#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/98/2239884.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_2239884
loop_
_publ_author_name
'Singh, Pushpendra'
'Singh, Harkesh B.'
'Butcher, Ray J.'
_publ_section_title
;
 Crystal structure of
 N¹-benzyl-N¹,N²,N²-trimethylethane-1,2-diaminium
 dichloride
;
_journal_coeditor_code           HB7244
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o911
_journal_page_last               o912
_journal_paper_doi               10.1107/S1600536814015797
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C12 H22 N2 2+, 2Cl -'
_chemical_formula_moiety         'C12 H22 N2 2+, 2(Cl -)'
_chemical_formula_sum            'C12 H22 Cl2 N2'
_chemical_formula_weight         265.21
_chemical_name_systematic
'N¹-Benzyl-N¹,N²,N²-trimethylethane-1,2-diaminium dichloride'
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 105.372(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6744(7)
_cell_length_b                   22.384(3)
_cell_length_c                   5.9991(7)
_cell_measurement_reflns_used    1555
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      76.40
_cell_measurement_theta_min      3.95
_cell_volume                     734.72(16)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2012)
;
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.915
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_device_type  'Agilent Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2002
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         76.585
_diffrn_reflns_theta_min         3.950
_exptl_absorpt_coefficient_mu    3.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2012)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.150
_refine_diff_density_min         -0.624
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.25(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1986
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0823
_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)+(0.1591P)²+1.0863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2283
_refine_ls_wR_factor_ref         0.2290
_reflns_number_gt                1961
_reflns_number_total             1986
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7244sup1.cif
_cod_data_source_block           I
_cod_database_code               2239884
_cod_database_fobs_code          2239884
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelxl_version_number           .2013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
Cl Cl1 0.5443(3) 0.30227(7) 1.3350(2) 0.0313(4) Uani d 1
Cl Cl2 -0.5635(2) 0.48206(5) 0.67629(19) 0.0219(3) Uani d 1
N N1 0.0818(16) 0.3087(4) 0.9195(14) 0.052(2) Uani d 1
H H1A 0.2296 0.3060 1.0540 0.063 Uiso calc 1
N N2 -0.0884(18) 0.4633(5) 1.083(2) 0.061(2) Uani d 1
H H2B -0.2225 0.4640 0.9363 0.074 Uiso calc 1
C C1 0.092(2) 0.1998(6) 0.814(2) 0.065(3) Uani d 1
C C2 -0.012(3) 0.1787(6) 0.583(2) 0.078(4) Uani d 1
H H2A -0.1656 0.1919 0.4903 0.094 Uiso calc 1
C C3 0.141(3) 0.1344(6) 0.500(2) 0.075(3) Uani d 1
H H3A 0.0818 0.1180 0.3493 0.090 Uiso calc 1
C C4 0.359(3) 0.1172(6) 0.629(3) 0.092(4) Uani d 1
H H4A 0.4563 0.0907 0.5670 0.110 Uiso calc 1
C C5 0.446(3) 0.1374(7) 0.855(3) 0.094(5) Uani d 1
H H5A 0.6003 0.1239 0.9458 0.113 Uiso calc 1
C C6 0.310(2) 0.1772(6) 0.950(2) 0.074(3) Uani d 1
H H6A 0.3662 0.1887 1.1075 0.088 Uiso calc 1
C C7 -0.044(3) 0.2487(6) 0.896(2) 0.067(3) Uani d 1
H H7A -0.0677 0.2372 1.0479 0.080 Uiso calc 1
H H7B -0.2077 0.2525 0.7861 0.080 Uiso calc 1
C C8 0.171(2) 0.3228(4) 0.7060(17) 0.050(2) Uani d 1
H H8A 0.2488 0.3622 0.7239 0.074 Uiso calc 1
H H8B 0.0318 0.3227 0.5683 0.074 Uiso calc 1
H H8C 0.2896 0.2925 0.6890 0.074 Uiso calc 1
C C9 -0.065(2) 0.3554(5) 0.967(2) 0.057(3) Uani d 1
H H9A -0.1454 0.3416 1.0862 0.069 Uiso calc 1
H H9B -0.1955 0.3646 0.8253 0.069 Uiso calc 1
C C10 0.079(2) 0.4127(6) 1.0534(19) 0.058(3) Uani d 1
H H10A 0.1997 0.4047 1.2031 0.069 Uiso calc 1
H H10B 0.1706 0.4249 0.9411 0.069 Uiso calc 1
C C11 -0.205(3) 0.4576(7) 1.257(3) 0.075(4) Uani d 1
H H11A -0.0833 0.4579 1.4077 0.113 Uiso calc 1
H H11B -0.2958 0.4198 1.2383 0.113 Uiso calc 1
H H11C -0.3186 0.4910 1.2494 0.113 Uiso calc 1
C C12 0.045(3) 0.5223(6) 1.088(2) 0.066(3) Uani d 1
H H12A -0.0741 0.5546 1.0381 0.099 Uiso calc 1
H H12B 0.1517 0.5202 0.9838 0.099 Uiso calc 1
H H12C 0.1441 0.5304 1.2459 0.099 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C9 N1 C7 112.7(9)
C9 N1 C8 111.3(9)
C7 N1 C8 111.0(8)
C9 N1 H1A 107.2
C7 N1 H1A 107.2
C8 N1 H1A 107.2
C11 N2 C10 117.4(11)
C11 N2 C12 113.6(11)
C10 N2 C12 109.0(9)
C11 N2 H2B 105.2
C10 N2 H2B 105.2
C12 N2 H2B 105.2
C6 C1 C2 121.6(13)
C6 C1 C7 122.1(12)
C2 C1 C7 116.3(12)
C1 C2 C3 114.6(13)
C1 C2 H2A 122.7
C3 C2 H2A 122.7
C4 C3 C2 122.1(13)
C4 C3 H3A 118.9
C2 C3 H3A 118.9
C3 C4 C5 120.6(15)
C3 C4 H4A 119.7
C5 C4 H4A 119.7
C4 C5 C6 121.0(14)
C4 C5 H5A 119.5
C6 C5 H5A 119.5
C1 C6 C5 119.7(13)
C1 C6 H6A 120.1
C5 C6 H6A 120.1
C1 C7 N1 114.2(11)
C1 C7 H7A 108.7
N1 C7 H7A 108.7
C1 C7 H7B 108.7
N1 C7 H7B 108.7
H7A C7 H7B 107.6
N1 C8 H8A 109.5
N1 C8 H8B 109.5
H8A C8 H8B 109.5
N1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N1 C9 C10 113.1(9)
N1 C9 H9A 109.0
C10 C9 H9A 109.0
N1 C9 H9B 109.0
C10 C9 H9B 109.0
H9A C9 H9B 107.8
N2 C10 C9 111.4(9)
N2 C10 H10A 109.3
C9 C10 H10A 109.3
N2 C10 H10B 109.3
C9 C10 H10B 109.3
H10A C10 H10B 108.0
N2 C11 H11A 109.5
N2 C11 H11B 109.5
H11A C11 H11B 109.5
N2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
N2 C12 H12A 109.5
N2 C12 H12B 109.5
H12A C12 H12B 109.5
N2 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C9 1.413(15)
N1 C7 1.511(17)
N1 C8 1.530(14)
N1 H1A 1.0000
N2 C11 1.38(2)
N2 C10 1.520(16)
N2 C12 1.521(17)
N2 H2B 1.0000
C1 C6 1.382(18)
C1 C2 1.435(18)
C1 C7 1.497(18)
C2 C3 1.49(2)
C2 H2A 0.9500
C3 C4 1.33(2)
C3 H3A 0.9500
C4 C5 1.39(2)
C4 H4A 0.9500
C5 C6 1.40(2)
C5 H5A 0.9500
C6 H6A 0.9500
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C10 1.538(16)
C9 H9A 0.9900
C9 H9B 0.9900
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
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 H1A Cl1 . 1.00 2.11 3.107(8) 179
N2 H2B Cl2 . 1.00 2.18 3.148(11) 163
C7 H7B Cl1 1_454 0.99 2.92 3.749(13) 142
C8 H8A Cl2 1_655 0.98 2.93 3.893(10) 168
C8 H8B Cl1 1_454 0.98 2.79 3.690(11) 154
C8 H8C Cl1 1_554 0.98 2.88 3.486(12) 121
C9 H9A Cl1 1_455 0.99 2.74 3.711(12) 168
C10 H10A Cl1 . 0.99 2.98 3.682(11) 129
C10 H10B Cl2 1_655 0.99 2.78 3.750(13) 168
C11 H11B Cl1 1_455 0.98 2.89 3.831(17) 161
C12 H12B Cl2 1_655 0.98 2.89 3.842(15) 166
C12 H12C Cl2 1_656 0.98 2.88 3.747(13) 147
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
C6 C1 C2 C3 -4(2)
C7 C1 C2 C3 174.3(12)
C1 C2 C3 C4 -1(2)
C2 C3 C4 C5 4(2)
C3 C4 C5 C6 -1(3)
C2 C1 C6 C5 7(2)
C7 C1 C6 C5 -171.5(14)
C4 C5 C6 C1 -4(2)
C6 C1 C7 N1 69.3(16)
C2 C1 C7 N1 -108.9(14)
C9 N1 C7 C1 172.2(10)
C8 N1 C7 C1 46.6(13)
C7 N1 C9 C10 165.1(9)
C8 N1 C9 C10 -69.5(11)
C11 N2 C10 C9 67.8(13)
C12 N2 C10 C9 -161.2(10)
N1 C9 C10 N2 175.1(10)
