#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/64/2226486.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_2226486
loop_
_publ_author_name
'Yu, Shu-Lan'
_publ_section_title
;
 2-Methylpropan-2-aminium 4-hydroxybenzoate
;
_journal_coeditor_code           HB5493
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1706
_journal_paper_doi               10.1107/S1600536810022592
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C4 H12 N +, C7 H5 O3 -'
_chemical_formula_moiety         'C4 H12 N +, C7 H5 O3 -'
_chemical_formula_sum            'C11 H17 N O3'
_chemical_formula_weight         211.26
_chemical_name_systematic
;
2-Methylpropan-2-aminium 4-hydroxybenzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 99.58(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8300(14)
_cell_length_b                   9.2790(19)
_cell_length_c                   19.831(4)
_cell_measurement_reflns_used    1804
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.96
_cell_measurement_theta_min      2.08
_cell_volume                     1239.3(5)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'phi and omega 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  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            2899
_diffrn_reflns_theta_full        26.96
_diffrn_reflns_theta_max         26.96
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bar
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.294
_refine_ls_extinction_coef       0.59(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2677
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0565
_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)+(0.0928P)²+0.1735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1679
_reflns_number_gt                1804
_reflns_number_total             2677
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5493.cif
_cod_data_source_block           I
_cod_original_cell_volume        1239.3(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226486
_cod_database_fobs_code          2226486
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1770(3) 0.81042(19) 0.40216(9) 0.0475(4) Uani d . 1 . .
C C2 0.2054(2) 0.70697(18) 0.34696(8) 0.0435(4) Uani d . 1 . .
C C3 0.3911(3) 0.6882(2) 0.32850(10) 0.0618(6) Uani d . 1 . .
H H3A 0.4999 0.7372 0.3523 0.074 Uiso calc R 1 . .
C C4 0.4170(3) 0.5976(3) 0.27512(12) 0.0728(7) Uani d . 1 . .
H H4A 0.5423 0.5872 0.2632 0.087 Uiso calc R 1 . .
C C5 0.2577(3) 0.5225(2) 0.23940(10) 0.0571(5) Uani d . 1 . .
C C6 0.0722(3) 0.5367(2) 0.25849(10) 0.0558(5) Uani d . 1 . .
H H6A -0.0351 0.4843 0.2359 0.067 Uiso calc R 1 . .
C C7 0.0470(2) 0.6290(2) 0.31113(9) 0.0513(5) Uani d . 1 . .
H H7A -0.0785 0.6393 0.3229 0.062 Uiso calc R 1 . .
O O1 0.00062(19) 0.84869(15) 0.40644(6) 0.0606(4) Uani d . 1 . .
O O2 0.3246(2) 0.85859(16) 0.44198(7) 0.0667(5) Uani d . 1 . .
O O3 0.2922(2) 0.4377(2) 0.18682(9) 0.0863(6) Uani d . 1 . .
H H3B 0.1865 0.4187 0.1622 0.129 Uiso calc R 1 . .
C C8 0.7450(4) 0.6075(3) 0.50722(16) 0.0949(9) Uani d . 1 . .
H H8A 0.6109 0.6040 0.4832 0.142 Uiso calc R 1 . .
H H8B 0.7693 0.5259 0.5372 0.142 Uiso calc R 1 . .
H H8C 0.8352 0.6053 0.4749 0.142 Uiso calc R 1 . .
C C9 0.6313(5) 0.7601(4) 0.59955(17) 0.1178(12) Uani d . 1 . .
H H9A 0.6486 0.8522 0.6218 0.177 Uiso calc R 1 . .
H H9B 0.6563 0.6850 0.6331 0.177 Uiso calc R 1 . .
H H9C 0.4977 0.7520 0.5754 0.177 Uiso calc R 1 . .
C C10 0.9911(4) 0.7600(3) 0.58411(13) 0.0806(7) Uani d . 1 . .
H H10A 1.0103 0.8519 0.6065 0.121 Uiso calc R 1 . .
H H10B 1.0772 0.7522 0.5507 0.121 Uiso calc R 1 . .
H H10C 1.0213 0.6845 0.6173 0.121 Uiso calc R 1 . .
C C11 0.7764(3) 0.7461(2) 0.54907(11) 0.0632(6) Uani d . 1 . .
N N1 0.7346(2) 0.86993(18) 0.49897(8) 0.0483(4) Uani d . 1 . .
H H1 0.734(3) 0.958(2) 0.5202(10) 0.058 Uiso d . 1 . .
H H2 0.815(3) 0.869(2) 0.4690(12) 0.058 Uiso d . 1 . .
H H3 0.608(3) 0.859(2) 0.4718(10) 0.058 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 C1 O1 . . 121.95(16) ?
O2 C1 C2 . . 120.11(16) ?
O1 C1 C2 . . 117.93(15) ?
C3 C2 C7 . . 117.80(15) ?
C3 C2 C1 . . 120.66(15) ?
C7 C2 C1 . . 121.53(15) ?
C4 C3 C2 . . 121.05(17) ?
C4 C3 H3A . . 119.5 ?
C2 C3 H3A . . 119.5 ?
C5 C4 C3 . . 120.47(18) ?
C5 C4 H4A . . 119.8 ?
C3 C4 H4A . . 119.8 ?
O3 C5 C4 . . 117.57(17) ?
O3 C5 C6 . . 123.22(17) ?
C4 C5 C6 . . 119.21(17) ?
C7 C6 C5 . . 119.93(16) ?
C7 C6 H6A . . 120.0 ?
C5 C6 H6A . . 120.0 ?
C6 C7 C2 . . 121.50(16) ?
C6 C7 H7A . . 119.3 ?
C2 C7 H7A . . 119.3 ?
C5 O3 H3B . . 109.5 ?
C11 C8 H8A . . 109.5 ?
C11 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C11 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C11 C9 H9A . . 109.5 ?
C11 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C11 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C11 C10 H10A . . 109.5 ?
C11 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C11 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N1 C11 C10 . . 107.33(16) ?
N1 C11 C8 . . 106.78(18) ?
C10 C11 C8 . . 110.92(19) ?
N1 C11 C9 . . 107.08(19) ?
C10 C11 C9 . . 112.0(2) ?
C8 C11 C9 . . 112.4(2) ?
C11 N1 H1 . . 113.0(13) ?
C11 N1 H2 . . 111.4(13) ?
H1 N1 H2 . . 111.9(19) ?
C11 N1 H3 . . 110.4(12) ?
H1 N1 H3 . . 106.4(18) ?
H2 N1 H3 . . 103.3(18) ?
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 O2 . 1.255(2) ?
C1 O1 . 1.272(2) ?
C1 C2 . 1.493(2) ?
C2 C3 . 1.388(2) ?
C2 C7 . 1.394(2) ?
C3 C4 . 1.386(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.384(3) ?
C4 H4A . 0.9300 ?
C5 O3 . 1.358(2) ?
C5 C6 . 1.388(3) ?
C6 C7 . 1.383(3) ?
C6 H6A . 0.9300 ?
C7 H7A . 0.9300 ?
O3 H3B . 0.8200 ?
C8 C11 . 1.527(3) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C11 . 1.527(3) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C11 . 1.520(3) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 N1 . 1.515(2) ?
N1 H1 . 0.92(2) ?
N1 H2 . 0.87(2) ?
N1 H3 . 0.94(2) ?
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
O3 H3B O1 2_545 0.82 1.83 2.621(2) 163
N1 H1 O2 3_676 0.92(2) 1.93(2) 2.835(2) 168.2(18)
N1 H3 O2 . 0.94(2) 1.93(2) 2.842(2) 162.2(18)
N1 H2 O1 1_655 0.87(2) 1.92(3) 2.796(2) 174.7(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656120
