#------------------------------------------------------------------------------
#$Date: 2016-07-30 04:26:18 +0300 (Sat, 30 Jul 2016) $
#$Revision: 184734 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/17/2241794.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_2241794
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_iupac          'C2 H9 N2 +, H2 P O3 -'
_chemical_formula_moiety         'C2 H9 N2 +, H2 O3 P -'
_chemical_formula_sum            'C2 H11 N2 O3 P'
_chemical_formula_weight         142.10
_chemical_name_systematic
;
2,2-Dimethylhydrazin-1-ium dihydrogen phosphite
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0690(2)
_cell_length_b                   6.9970(2)
_cell_length_c                   11.7001(6)
_cell_measurement_reflns_used    4031
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.37
_cell_volume                     660.57(4)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0232
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5347
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.393
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.279
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.15(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         1395
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0249
_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)+(0.0374P)²+0.2030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0645
_reflns_number_gt                1365
_reflns_number_total             1395
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5314sup1.cif
_cod_data_source_block           II
_cod_database_code               2241794
_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, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -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
N N1 0.5416(2) 0.5852(2) 0.22552(17) 0.0132(4) Uani d 1
H H1n 0.6455 0.5972 0.1962 0.016 Uiso calc 1
H H2n 0.4779 0.6848 0.2016 0.016 Uiso calc 1
H H3n 0.4960 0.4735 0.2011 0.016 Uiso calc 1
N N2 0.5499(2) 0.5853(3) 0.34964(17) 0.0145(4) Uani d 1
C C1 0.3807(3) 0.5724(3) 0.3936(3) 0.0189(5) Uani d 1
H H1a 0.3169 0.6834 0.3677 0.028 Uiso calc 1
H H1b 0.3832 0.5699 0.4773 0.028 Uiso calc 1
H H1c 0.3286 0.4551 0.3652 0.028 Uiso calc 1
C C2 0.6471(3) 0.4186(3) 0.3845(2) 0.0206(5) Uani d 1
H H2a 0.7575 0.4255 0.3499 0.031 Uiso calc 1
H H2b 0.5912 0.3018 0.3590 0.031 Uiso calc 1
H H2c 0.6576 0.4169 0.4679 0.031 Uiso calc 1
P P1 0.45797(6) 0.05934(7) 0.10615(6) 0.01209(15) Uani d 1
H H1 0.4666 0.0529 -0.0064 0.015 Uiso calc 1
O O1 0.35870(18) -0.1101(2) 0.14409(14) 0.0153(3) Uani d 1
O O2 0.39202(17) 0.2526(2) 0.13797(14) 0.0165(4) Uani d 1
O O3 0.63746(19) 0.0285(2) 0.15307(17) 0.0196(4) Uani d 1
H H1o 0.7059 0.1224 0.1417 0.024 Uiso 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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 109.5
N2 N1 H2n 109.5
H1n N1 H2n 109.5
N2 N1 H3n 109.5
H1n N1 H3n 109.5
H2n N1 H3n 109.5
N1 N2 C1 107.94(18)
N1 N2 C2 107.62(17)
C1 N2 C2 110.69(18)
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
O1 P1 O2 116.76(9)
O1 P1 O3 106.37(9)
O2 P1 O3 111.46(9)
O1 P1 H1 107.3
O2 P1 H1 107.3
O3 P1 H1 107.3
P1 O3 H1o 115.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.454(3)
N1 H1n 0.91
N1 H2n 0.91
N1 H3n 0.91
N2 C1 1.462(3)
N2 C2 1.463(3)
C1 H1a 0.98
C1 H1b 0.98
C1 H1c 0.98
C2 H2a 0.98
C2 H2b 0.98
C2 H2c 0.98
P1 O1 1.4982(15)
P1 O2 1.5003(16)
P1 O3 1.5638(16)
P1 H1 1.32
O3 H1o 0.8689
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 O1 4 0.91 1.83 2.736(2) 176
N1 H2n O1 1_565 0.91 1.85 2.762(2) 176
N1 H3n O2 . 0.91 1.91 2.814(2) 175
O3 H1o O2 4 0.87 1.74 2.568(2) 159

_cod_database_fobs_code 2241794
