#------------------------------------------------------------------------------
#$Date: 2016-07-30 04:26:18 +0300 (Sat, 30 Jul 2016) $
#$Revision: 184734 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/17/2241793.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_2241793
loop_
_publ_author_name
'Katinaitė, Judita'
'Harrison, William T. A.'
_publ_section_title
;
 Different cation-protonation patterns in molecular salts of unsymmetrical
 dimethyhydrazine: C₂H₉N₂·Br and
 C₂H₉N₂·H₂PO₃
;
_journal_coeditor_code           SU5314
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1206
_journal_page_last               1210
_journal_paper_doi               10.1107/S2056989016011993
_journal_volume                  72
_journal_year                    2016
_chemical_formula_moiety         'C2 H9 N2 +, Br -'
_chemical_formula_sum            'C2 H9 Br N2'
_chemical_formula_weight         141.02
_chemical_name_systematic
;
1,1-Dimethylhydrazin-1-ium bromide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.838(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2423(2)
_cell_length_b                   5.12390(10)
_cell_length_c                   16.1839(3)
_cell_measurement_reflns_used    5743
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.52
_cell_volume                     1094.20(3)
_computing_cell_refinement
;
CrystalClear (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear (Rigaku, 2012)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6485
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.526
_exptl_absorpt_coefficient_mu    7.361
_exptl_absorpt_correction_T_max  0.557
_exptl_absorpt_correction_T_min  0.282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrystalClear; Rigaku, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_description       rod
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.475
_refine_ls_extinction_coef       0.0151(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         1258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0202
_refine_ls_R_factor_gt           0.0197
_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)+(0.0349P)²+0.3874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0506
_refine_ls_wR_factor_ref         0.0509
_reflns_number_gt                1224
_reflns_number_total             1258
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5314sup1.cif
_cod_data_source_block           I
_cod_database_code               2241793
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
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
N N1 0.13506(11) 0.3029(3) 0.30499(9) 0.0197(3) Uani d 1
H H1n 0.1888(17) 0.204(4) 0.3204(13) 0.024 Uiso d 1
H H2n 0.1477(17) 0.393(3) 0.2599(15) 0.024 Uiso d 1
N N2 0.13068(10) 0.4851(2) 0.37297(8) 0.0170(3) Uani d 1
H H3n 0.1867(17) 0.574(4) 0.3765(12) 0.020 Uiso d 1
C C1 0.11750(14) 0.3372(3) 0.45000(11) 0.0191(3) Uani d 1
H H1a 0.1708 0.2047 0.4582 0.029 Uiso calc 1
H H1b 0.0510 0.2519 0.4454 0.029 Uiso calc 1
H H1c 0.1220 0.4571 0.4973 0.029 Uiso calc 1
C C2 0.04544(15) 0.6693(3) 0.35325(15) 0.0278(4) Uani d 1
H H2a 0.0567 0.7656 0.3025 0.042 Uiso calc 1
H H2b 0.0416 0.7925 0.3992 0.042 Uiso calc 1
H H2c -0.0182 0.5715 0.3450 0.042 Uiso calc 1
Br Br1 0.17057(2) 0.64136(3) 0.12100(2) 0.01501(11) 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 0.0033 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'
Br Br -0.2901 2.4595 '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
N2 N1 H1n 103.6(14)
N2 N1 H2n 108.0(12)
H1n N1 H2n 108.8(19)
N1 N2 C1 108.93(12)
N1 N2 C2 108.97(14)
C1 N2 C2 111.38(14)
N1 N2 H3n 107.4(13)
C1 N2 H3n 111.9(13)
C2 N2 H3n 108.1(13)
N2 C1 H1a 109.5
N2 C1 H1b 109.5
H1a C1 H1b 109.5
N2 C1 H1c 109.5
H1a C1 H1c 109.5
H1b C1 H1c 109.5
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.4478(19)
N1 H1n 0.89(2)
N1 H2n 0.89(2)
N2 C1 1.482(2)
N2 C2 1.485(2)
N2 H3n 0.87(2)
C1 H1a 0.98
C1 H1b 0.98
C1 H1c 0.98
C2 H2a 0.98
C2 H2b 0.98
C2 H2c 0.98
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 H1n Br1 7 0.89(2) 2.68(3) 3.5666(15) 170.7(18)
N1 H2n Br1 . 0.89(2) 2.62(2) 3.5117(14) 175.0(19)
N2 H3n Br1 7_565 0.87(2) 2.39(2) 3.2490(13) 173.3(17)
C1 H1a Br1 7 0.98 3.11 3.9690(18) 148
C1 H1b Br1 4_445 0.98 3.09 4.0175(19) 158
C1 H1c Br1 8_565 0.98 2.90 3.8682(17) 168
C2 H2c Br1 4_445 0.98 3.07 3.9843(18) 156

_cod_database_fobs_code 2241793
