#------------------------------------------------------------------------------
#$Date: 2018-11-10 05:39:06 +0200 (Sat, 10 Nov 2018) $
#$Revision: 211893 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/27/2242731.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_2242731
loop_
_publ_author_name
'Wardell, James L.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Crystal structures of the 1:1 salts of 2-amino-4-nitrobenzoate with each
 of (2-hydroxyethyl)dimethylazanium,
 tert-butyl(2-hydroxyethyl)azanium and
 1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium
;
_journal_coeditor_code           HB7785
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1735
_journal_page_last               1740
_journal_paper_doi               10.1107/S2056989018015578
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C6 H16 N O +, C7 H5 N2 O4 -'
_chemical_formula_moiety         'C6 H16 N O +, C7 H5 N2 O4 -'
_chemical_formula_sum            'C13 H21 N3 O5'
_chemical_formula_weight         299.33
_chemical_name_systematic
;
2-Amino-4-nitrobenzoate tert-butyl(2-hydroxyethyl)azanium
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 120.627(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.1138(5)
_cell_length_b                   12.3635(5)
_cell_length_c                   13.1909(4)
_cell_measurement_reflns_used    8229
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2963.02(18)
_computing_cell_refinement
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_data_collection
;
COLLECT (Hooft, 1998)
;
_computing_data_reduction
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Bruker--Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker--Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18353
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         3.040
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2007)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       slab
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.331
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3406
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0499
_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)+(0.0712P)²+0.7685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1353
_reflns_number_gt                2349
_reflns_number_total             3406
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7785sup1.cif
_cod_data_source_block           II
_cod_original_cell_volume        2963.02(17)
_cod_database_code               2242731
_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.
;
_shelx_estimated_absorpt_t_min   0.939
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
O O1 0.38287(6) 0.76025(10) 0.01169(10) 0.0301(3) Uani d 1
O O2 0.29310(6) 0.63783(10) -0.04670(10) 0.0263(3) Uani d 1
O O3 0.63480(6) 0.33794(10) 0.24135(11) 0.0305(3) Uani d 1
O O4 0.54488(7) 0.22405(10) 0.17418(13) 0.0400(4) Uani d 1
N N1 0.52324(7) 0.69991(12) 0.14202(13) 0.0241(3) Uani d 1
N N2 0.56872(7) 0.31665(12) 0.18823(12) 0.0241(3) Uani d 1
C C1 0.41726(8) 0.57689(13) 0.05554(13) 0.0188(4) Uani d 1
C C2 0.49416(8) 0.59915(13) 0.12014(12) 0.0187(4) Uani d 1
C C3 0.54245(8) 0.51022(13) 0.16275(13) 0.0192(4) Uani d 1
H H3 0.5941 0.5221 0.2073 0.023 Uiso calc 1
C C4 0.51565(8) 0.40665(13) 0.14053(13) 0.0195(4) Uani d 1
C C5 0.44091(8) 0.38249(14) 0.07707(13) 0.0215(4) Uani d 1
H H5 0.4235 0.3101 0.0624 0.026 Uiso calc 1
C C6 0.39357(8) 0.46956(14) 0.03667(13) 0.0214(4) Uani d 1
H H6 0.3421 0.4558 -0.0063 0.026 Uiso calc 1
C C7 0.36039(8) 0.66455(14) 0.00382(13) 0.0216(4) Uani d 1
O O5 0.69062(6) 0.71809(10) 0.29593(11) 0.0303(3) Uani d 1
N N3 0.79731(7) 0.56819(12) 0.45647(12) 0.0231(3) Uani d 1
C C8 0.84793(9) 0.47891(15) 0.53503(16) 0.0292(4) Uani d 1
C C9 0.80464(11) 0.37480(16) 0.5120(2) 0.0444(5) Uani d 1
H H9A 0.7623 0.3876 0.5219 0.067 Uiso calc 1
H H9B 0.8363 0.3192 0.5678 0.067 Uiso calc 1
H H9C 0.7873 0.3503 0.4313 0.067 Uiso calc 1
C C10 0.87684(12) 0.51860(17) 0.66040(17) 0.0448(5) Uani d 1
H H10A 0.8355 0.5298 0.6732 0.067 Uiso calc 1
H H10B 0.9032 0.5870 0.6724 0.067 Uiso calc 1
H H10C 0.9104 0.4646 0.7163 0.067 Uiso calc 1
C C11 0.91074(10) 0.46495(17) 0.51089(19) 0.0402(5) Uani d 1
H H11A 0.9478 0.4160 0.5696 0.060 Uiso calc 1
H H11B 0.9333 0.5355 0.5155 0.060 Uiso calc 1
H H11C 0.8916 0.4344 0.4320 0.060 Uiso calc 1
C C12 0.75766(9) 0.54960(16) 0.32642(15) 0.0310(4) Uani d 1
H H12A 0.7141 0.5033 0.3028 0.037 Uiso calc 1
H H12B 0.7905 0.5118 0.3049 0.037 Uiso calc 1
C C13 0.73361(9) 0.65690(16) 0.26214(15) 0.0301(4) Uani d 1
H H13A 0.7777 0.6992 0.2789 0.036 Uiso calc 1
H H13B 0.7046 0.6434 0.1762 0.036 Uiso calc 1
H H1N 0.4925(9) 0.7539(12) 0.1137(17) 0.036 Uiso d 1
H H2N 0.5715(5) 0.7082(16) 0.1885(15) 0.036 Uiso d 1
H H5O 0.7197(10) 0.7625(14) 0.3464(15) 0.045 Uiso d 1
H H3N 0.8263(9) 0.6272(11) 0.4739(16) 0.036 Uiso d 1
H H4N 0.7637(8) 0.5810(16) 0.4767(16) 0.036 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
C2 N1 H1N 117.1(13)
C2 N1 H2N 119.3(13)
H1N N1 H2N 123.4(19)
O4 N2 O3 123.05(14)
O4 N2 C4 118.44(13)
O3 N2 C4 118.50(14)
C6 C1 C2 119.11(14)
C6 C1 C7 118.37(13)
C2 C1 C7 122.50(14)
N1 C2 C3 118.44(13)
N1 C2 C1 124.09(14)
C3 C2 C1 117.46(14)
C4 C3 C2 120.56(14)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 123.22(15)
C3 C4 N2 118.23(13)
C5 C4 N2 118.54(14)
C6 C5 C4 116.24(15)
C6 C5 H5 121.9
C4 C5 H5 121.9
C5 C6 C1 123.40(14)
C5 C6 H6 118.3
C1 C6 H6 118.3
O1 C7 O2 124.24(15)
O1 C7 C1 117.45(13)
O2 C7 C1 118.31(15)
C13 O5 H5O 105.7(15)
C12 N3 C8 117.35(14)
C12 N3 H3N 109.1(12)
C8 N3 H3N 105.3(12)
C12 N3 H4N 107.8(12)
C8 N3 H4N 108.4(13)
H3N N3 H4N 108.6(18)
C9 C8 N3 109.71(14)
C9 C8 C11 111.21(16)
N3 C8 C11 108.94(15)
C9 C8 C10 111.00(17)
N3 C8 C10 105.08(14)
C11 C8 C10 110.70(16)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C8 C10 H10A 109.5
C8 C10 H10B 109.5
H10A C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C8 C11 H11A 109.5
C8 C11 H11B 109.5
H11A C11 H11B 109.5
C8 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
N3 C12 C13 109.85(14)
N3 C12 H12A 109.7
C13 C12 H12A 109.7
N3 C12 H12B 109.7
C13 C12 H12B 109.7
H12A C12 H12B 108.2
O5 C13 C12 112.15(15)
O5 C13 H13A 109.2
C12 C13 H13A 109.2
O5 C13 H13B 109.2
C12 C13 H13B 109.2
H13A C13 H13B 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.259(2)
O2 C7 1.2678(19)
O3 N2 1.2292(17)
O4 N2 1.2262(18)
N1 C2 1.353(2)
N1 H1N 0.872(9)
N1 H2N 0.887(9)
N2 C4 1.473(2)
C1 C6 1.395(2)
C1 C2 1.424(2)
C1 C7 1.499(2)
C2 C3 1.407(2)
C3 C4 1.370(2)
C3 H3 0.9500
C4 C5 1.391(2)
C5 C6 1.378(2)
C5 H5 0.9500
C6 H6 0.9500
O5 C13 1.417(2)
O5 H5O 0.841(10)
N3 C12 1.494(2)
N3 C8 1.519(2)
N3 H3N 0.903(9)
N3 H4N 0.890(9)
C8 C9 1.517(3)
C8 C11 1.523(3)
C8 C10 1.523(3)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C13 1.516(3)
C12 H12A 0.9900
C12 H12B 0.9900
C13 H13A 0.9900
C13 H13B 0.9900
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 . 0.871(18) 2.00(2) 2.665(2) 132.3(15)
N1 H2N O5 . 0.888(16) 2.172(15) 3.058(2) 175.8(18)
N3 H3N O1 8_565 0.904(17) 1.733(17) 2.637(2) 178(2)
N3 H4N O2 2_655 0.89(2) 1.98(2) 2.849(2) 165.6(17)
O5 H5O O2 8_565 0.840(18) 1.919(18) 2.7546(18) 173(2)
C11 H11A O4 8_555 0.98 2.49 3.450(3) 165
C12 H12A O3 . 0.99 2.50 3.445(2) 159
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 N1 178.92(14)
C7 C1 C2 N1 0.6(2)
C6 C1 C2 C3 -0.6(2)
C7 C1 C2 C3 -178.87(13)
N1 C2 C3 C4 -178.52(14)
C1 C2 C3 C4 1.0(2)
C2 C3 C4 C5 -0.6(2)
C2 C3 C4 N2 -179.45(13)
O4 N2 C4 C3 176.00(14)
O3 N2 C4 C3 -3.2(2)
O4 N2 C4 C5 -2.9(2)
O3 N2 C4 C5 177.91(14)
C3 C4 C5 C6 -0.2(2)
N2 C4 C5 C6 178.59(13)
C4 C5 C6 C1 0.7(2)
C2 C1 C6 C5 -0.3(2)
C7 C1 C6 C5 178.09(14)
C6 C1 C7 O1 -173.13(14)
C2 C1 C7 O1 5.2(2)
C6 C1 C7 O2 5.6(2)
C2 C1 C7 O2 -176.12(14)
C12 N3 C8 C9 -58.0(2)
C12 N3 C8 C11 63.99(19)
C12 N3 C8 C10 -177.36(15)
C8 N3 C12 C13 -159.11(14)
N3 C12 C13 O5 -55.18(18)

_cod_database_fobs_code 2242731
