#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/47/2014758.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_2014758
loop_
_publ_author_name
'Genivaldo Julio Perpétuo'
'Jan Janczak'
_publ_section_title
;
 Tetramethylammonium 2,5-dinitrophenolate monohydrate
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o165
_journal_page_last               o167
_journal_paper_doi               10.1107/S0108270105001253
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C4 H12 N +, C6 H3 N2 O5 -, H2 O'
_chemical_formula_moiety         'C4 H12 N +, C6 H3 N2 O5 -, H2 O'
_chemical_formula_sum            'C10 H17 N3 O6'
_chemical_formula_weight         275.27
_chemical_name_systematic
;
Tetramethylammonium 2,5-dinitrophenolate monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                106.38(2)
_cell_angle_beta                 104.80(2)
_cell_angle_gamma                102.23(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8080(10)
_cell_length_b                   9.995(2)
_cell_length_c                   11.421(2)
_cell_measurement_reflns_used    1225
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      3.19
_cell_volume                     686.3(3)
_computing_cell_refinement       'KM-4 CCD Software'
_computing_data_collection       'KM-4 CCD Software (Kuma, 2001)'
_computing_data_reduction        'KM-4 CCD Software'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Kuma KM-4'
_diffrn_measurement_method       '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  0.0123
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8043
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9735
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(face-indexed; SHELXTL; Sheldrick, 1990)
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      1.33
_exptl_crystal_density_method
;
floatation in the mixture of chloroform/1,2-dichloropropane
;
_exptl_crystal_description       paralellepiped
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.119
_refine_ls_extinction_coef       0.037(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0358
_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)+(0.0192P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0561
_refine_ls_wR_factor_ref         0.0639
_reflns_number_gt                2196
_reflns_number_total             3291
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sx1165.cif
_cod_data_source_block           I
_cod_database_code               2014758
_cod_database_fobs_code          2014758
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.29807(18) 0.18171(14) 0.49353(12) 0.0515(3) Uani d . 1 . . C
C2 0.31451(18) 0.09588(14) 0.57434(12) 0.0484(3) Uani d . 1 . . C
C3 0.24927(18) -0.05542(14) 0.52451(13) 0.0487(3) Uani d . 1 . . C
H3 0.2631 -0.1062 0.5815 0.064 Uiso calc R 1 . . H
C4 0.16540(18) -0.13276(13) 0.39477(13) 0.0523(3) Uani d . 1 . . C
H4 0.1218 -0.2346 0.3619 0.064 Uiso calc R 1 . . H
C5 0.14844(17) -0.05180(14) 0.31420(11) 0.0509(3) Uani d . 1 . . C
C6 0.20846(18) 0.09638(13) 0.35884(12) 0.0507(3) Uani d . 1 . . C
H6 0.1906 0.1440 0.2995 0.061 Uiso calc R 1 . . H
N1 0.40279(18) 0.16458(15) 0.71323(11) 0.0562(3) Uani d . 1 . . N
N2 0.06143(17) -0.12978(15) 0.17232(11) 0.0565(3) Uani d . 1 . . N
O1 0.35274(15) 0.32038(10) 0.53181(8) 0.0812(3) Uani d . 1 . . O
O2 0.4716(2) 0.29680(14) 0.76263(10) 0.0724(5) Uani d . 1 . . O
O3 0.41611(18) 0.08932(12) 0.78045(9) 0.0617(4) Uani d . 1 . . O
O4 0.00922(18) -0.26199(12) 0.13078(10) 0.0630(4) Uani d . 1 . . O
O5 0.04471(18) -0.05940(12) 0.10185(9) 0.0694(4) Uani d . 1 . . O
N3 0.66820(17) 0.32464(11) 0.16506(9) 0.0603(3) Uani d . 1 . . N
O6 0.24871(16) 0.46115(12) 0.35502(11) 0.0937(4) Uani d . 1 . . O
H61 0.289(3) 0.4125(18) 0.4118(17) 0.141 Uiso d . 1 . . H
H62 0.354(3) 0.5375(18) 0.3732(18) 0.141 Uiso d . 1 . . H
C7 0.7248(2) 0.37880(16) 0.30752(13) 0.0808(5) Uani d . 1 . . C
H7A 0.8752 0.3979 0.3471 0.126 Uiso calc R 1 . . H
H7B 0.6473 0.3062 0.3328 0.126 Uiso calc R 1 . . H
H7C 0.6885 0.4675 0.3353 0.126 Uiso calc R 1 . . H
C8 0.7793(3) 0.43892(16) 0.12623(17) 0.0798(6) Uani d . 1 . . C
H8A 0.7387 0.5256 0.1550 0.122 Uiso calc R 1 . . H
H8B 0.7409 0.4046 0.0336 0.122 Uiso calc R 1 . . H
H8C 0.9307 0.4612 0.1648 0.122 Uiso calc R 1 . . H
C9 0.7430(3) 0.19690(16) 0.12205(16) 0.0819(6) Uani d . 1 . . C
H9A 0.8916 0.2210 0.1701 0.128 Uiso calc R 1 . . H
H9B 0.7232 0.1709 0.0313 0.128 Uiso calc R 1 . . H
H9C 0.6627 0.1157 0.1368 0.128 Uiso calc R 1 . . H
C10 0.4361(3) 0.2863(2) 0.10159(16) 0.0879(7) Uani d . 1 . . C
H10A 0.3650 0.2003 0.1141 0.122 Uiso calc R 1 . . H
H10B 0.4049 0.2675 0.0105 0.122 Uiso calc R 1 . . H
H10C 0.3872 0.3661 0.1388 0.122 Uiso calc R 1 . . H
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C6 120.45(12) ?
O1 C1 C2 126.06(12) ?
C6 C1 C2 113.49(11) ?
C3 C2 C1 122.34(12) ?
C3 C2 N1 116.80(12) ?
C1 C2 N1 120.85(12) ?
C4 C3 C2 122.23(12) ?
C4 C3 H3 118.9 ?
C2 C3 H3 118.9 ?
C3 C4 C5 116.52(12) ?
C3 C4 H4 121.7 ?
C5 C4 H4 121.7 ?
C6 C5 C4 123.22(11) ?
C6 C5 N2 117.83(12) ?
C4 C5 N2 118.95(12) ?
C5 C6 C1 122.19(12) ?
C5 C6 H6 118.9 ?
C1 C6 H6 118.9 ?
O2 N1 O3 120.15(13) y
O2 N1 C2 119.96(13) ?
O3 N1 C2 119.81(13) ?
O4 N2 O5 122.24(13) y
O4 N2 C5 118.70(13) ?
O5 N2 C5 119.06(12) ?
C8 N3 C10 109.42(12) y
C8 N3 C9 106.68(12) y
C10 N3 C9 110.53(12) y
C8 N3 C7 109.32(11) y
C10 N3 C7 110.67(11) y
C9 N3 C7 110.13(11) y
H61 O6 H62 108.3(17) ?
N3 C7 H7A 109.5 ?
N3 C7 H7B 109.5 ?
H7A C7 H7B 109.5 ?
N3 C7 H7C 109.5 ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
N3 C8 H8A 109.5 ?
N3 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
N3 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
N3 C9 H9A 109.5 ?
N3 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
N3 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
N3 C10 H10A 109.5 ?
N3 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
N3 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.2677(13) y
C1 C6 . 1.4235(16) y
C1 C2 . 1.4264(16) y
C2 C3 . 1.3816(15) y
C2 N1 . 1.4397(16) y
C3 C4 . 1.3616(16) y
C3 H3 . 0.9300 ?
C4 C5 . 1.3857(15) y
C4 H4 . 0.9300 ?
C5 C6 . 1.3534(15) y
C5 N2 . 1.4785(16) y
C6 H6 . 0.9300 ?
N1 O2 . 1.2109(13) y
N1 O3 . 1.2176(13) y
N2 O4 . 1.2078(13) y
N2 O5 . 1.2091(13) y
N3 C8 . 1.4711(16) y
N3 C10 . 1.4732(17) y
N3 C9 . 1.4764(16) y
N3 C7 . 1.4776(15) y
O6 H61 . 0.936(17) ?
O6 H62 . 0.861(17) ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
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
_geom_hbond_publ_flag
O6 H61 O1 1_555 0.936(17) 1.868(17) 2.8021(15) 174.9(17) y
O6 H62 O1 2_666 0.861(17) 2.001(18) 2.8119(17) 156.5(17) y
