#------------------------------------------------------------------------------
#$Date: 2016-02-16 21:30:59 +0100 (mar 16 de feb de 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/13/4501307.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4501307
loop_
_publ_author_name
'Fujii, Kotaro'
'Sakon, Aya'
'Sekine, Akiko'
'Uekusa, Hidehiro'
_publ_section_title
;
 Reversible Color Switching of an Organic Crystal Induced by Organic
 Solvent Vapors
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4305
_journal_paper_doi               10.1021/cg2010437
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C8 H7 N O4, HO0.5'
_chemical_formula_sum            'C8 H8 N O4.5'
_chemical_formula_weight         190.15
_chemical_name_common            '5-aminoisophthalic acid hemihydrate'
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 94.266(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.1448(10)
_cell_length_b                   17.478(3)
_cell_length_c                   11.1576(15)
_cell_measurement_reflns_used    7673
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      3.21
_cell_volume                     1583.9(4)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_pressure         101.3
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7673
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.21
_diffrn_source                   'fine-focus rotating anode x-ray'
_diffrn_source_type              RIGAKU
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_correction_T_min  0.7295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'abscor Higashi RIGAKU'
_exptl_crystal_colour            'pale pink'
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_recrystallization_method evaporation
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         1816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0403
_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)+(0.0766P)²+0.1194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                1574
_reflns_number_total             1816
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg2010437_si_001.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        1584.0(4)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C8 H8 N O4.50'
_cod_database_code               4501307
loop_
_symmetry_equiv_pos_as_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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O5 O 0.0000 0.18191(6) 0.7500 0.0153(3) Uani 1 2 d S
H1A H 0.317(2) 0.6211(8) 0.7858(14) 0.028(4) Uiso 1 1 d .
H1B H 0.1520(17) 0.6142(8) 0.8407(14) 0.023(4) Uiso 1 1 d .
H1C H 0.1608(18) 0.6124(8) 0.7090(15) 0.026(4) Uiso 1 1 d .
H5 H 0.023(2) 0.2138(10) 0.8119(15) 0.041(5) Uiso 1 1 d .
H3 H 0.456(2) 0.2645(12) 0.5424(18) 0.056(6) Uiso 1 1 d .
O2 O 0.05510(10) 0.27856(5) 0.94191(7) 0.0205(2) Uani 1 1 d .
O3 O 0.39973(11) 0.28451(5) 0.60469(8) 0.0222(2) Uani 1 1 d .
O1 O 0.04443(9) 0.38225(4) 1.05775(7) 0.0160(2) Uani 1 1 d .
O4 O 0.42534(10) 0.39228(5) 0.49769(7) 0.0211(2) Uani 1 1 d .
N1 N 0.21367(11) 0.59871(5) 0.77937(8) 0.0138(2) Uani 1 1 d .
C5 C 0.30419(12) 0.39891(6) 0.68593(9) 0.0135(3) Uani 1 1 d .
C3 C 0.16338(12) 0.39415(6) 0.86948(9) 0.0128(2) Uani 1 1 d .
C6 C 0.29860(12) 0.47867(6) 0.68649(9) 0.0134(2) Uani 1 1 d .
H6 H 0.3428 0.5076 0.6243 0.016 Uiso 1 1 calc R
C2 C 0.16051(12) 0.47392(6) 0.87258(9) 0.0129(2) Uani 1 1 d .
H2 H 0.1141 0.5000 0.9367 0.015 Uiso 1 1 calc R
C8 C 0.38273(12) 0.35858(6) 0.58587(10) 0.0150(2) Uani 1 1 d .
C1 C 0.22659(11) 0.51472(6) 0.78052(9) 0.0124(2) Uani 1 1 d .
C4 C 0.23607(11) 0.35670(6) 0.77642(9) 0.0135(3) Uani 1 1 d .
H4 H 0.2393 0.3024 0.7746 0.016 Uiso 1 1 calc R
C7 C 0.08271(12) 0.34826(6) 0.96387(10) 0.0129(2) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O5 0.0202(5) 0.0135(5) 0.0127(6) 0.000 0.0033(4) 0.000
O2 0.0340(5) 0.0130(4) 0.0160(4) -0.0017(3) 0.0113(3) -0.0058(3)
O3 0.0342(5) 0.0156(4) 0.0187(5) -0.0017(3) 0.0138(3) 0.0031(3)
O1 0.0208(4) 0.0163(4) 0.0115(4) -0.0019(3) 0.0060(3) -0.0004(3)
O4 0.0289(5) 0.0223(5) 0.0131(4) 0.0020(3) 0.0080(3) 0.0036(3)
N1 0.0168(5) 0.0121(5) 0.0129(5) 0.0002(3) 0.0028(4) -0.0006(3)
C5 0.0130(5) 0.0167(5) 0.0111(5) -0.0014(4) 0.0019(4) -0.0005(4)
C3 0.0132(5) 0.0150(5) 0.0104(5) -0.0002(4) 0.0018(4) -0.0012(3)
C6 0.0131(5) 0.0164(5) 0.0110(5) 0.0006(4) 0.0020(4) -0.0011(4)
C2 0.0134(5) 0.0151(5) 0.0103(5) -0.0018(4) 0.0015(4) -0.0001(4)
C8 0.0154(5) 0.0177(5) 0.0120(5) -0.0015(4) 0.0023(4) 0.0001(4)
C1 0.0130(5) 0.0113(5) 0.0129(5) -0.0008(4) 0.0003(4) -0.0009(3)
C4 0.0144(5) 0.0128(5) 0.0133(6) -0.0013(4) 0.0017(4) -0.0010(3)
C7 0.0140(5) 0.0135(5) 0.0116(5) -0.0006(4) 0.0025(4) -0.0001(4)
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
C8 O3 H3 107.6(12)
C1 N1 H1A 110.8(9)
C1 N1 H1B 109.2(9)
H1A N1 H1B 111.2(13)
C1 N1 H1C 107.6(9)
H1A N1 H1C 109.2(14)
H1B N1 H1C 108.6(13)
C6 C5 C4 120.62(10)
C6 C5 C8 119.21(10)
C4 C5 C8 120.17(10)
C2 C3 C4 119.74(9)
C2 C3 C7 120.26(9)
C4 C3 C7 119.97(10)
C1 C6 C5 118.17(10)
C1 C6 H6 120.9
C5 C6 H6 120.9
C1 C2 C3 119.07(10)
C1 C2 H2 120.5
C3 C2 H2 120.5
O4 C8 O3 124.80(10)
O4 C8 C5 122.37(10)
O3 C8 C5 112.83(9)
C6 C1 C2 122.20(10)
C6 C1 N1 118.64(9)
C2 C1 N1 119.10(9)
C3 C4 C5 120.18(10)
C3 C4 H4 119.9
C5 C4 H4 119.9
O2 C7 O1 124.37(10)
O2 C7 C3 117.26(9)
O1 C7 C3 118.35(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O5 H5 0.896(17)
O2 C7 1.2596(13)
O3 C8 1.3172(14)
O3 H3 0.93(2)
O1 C7 1.2632(13)
O4 C8 1.2191(14)
N1 C1 1.4718(14)
N1 H1A 0.928(16)
N1 H1B 0.919(15)
N1 H1C 0.899(16)
C5 C6 1.3948(15)
C5 C4 1.3982(14)
C5 C8 1.5029(14)
C3 C2 1.3948(14)
C3 C4 1.3959(14)
C3 C7 1.5124(14)
C6 C1 1.3904(14)
C6 H6 0.9500
C2 C1 1.3912(14)
C2 H2 0.9500
C4 H4 0.9500
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
C4 C5 C6 C1 1.26(14)
C8 C5 C6 C1 -179.46(9)
C4 C3 C2 C1 1.73(14)
C7 C3 C2 C1 -176.04(9)
C6 C5 C8 O4 -8.51(15)
C4 C5 C8 O4 170.78(10)
C6 C5 C8 O3 171.36(9)
C4 C5 C8 O3 -9.36(14)
C5 C6 C1 C2 -0.18(14)
C5 C6 C1 N1 -177.44(9)
C3 C2 C1 C6 -1.32(14)
C3 C2 C1 N1 175.93(9)
C2 C3 C4 C5 -0.68(14)
C7 C3 C4 C5 177.09(9)
C6 C5 C4 C3 -0.84(14)
C8 C5 C4 C3 179.89(9)
C2 C3 C7 O2 163.89(10)
C4 C3 C7 O2 -13.88(14)
C2 C3 C7 O1 -14.65(14)
C4 C3 C7 O1 167.58(9)
