#------------------------------------------------------------------------------
#$Date: 2017-06-29 04:44:30 +0300 (Thu, 29 Jun 2017) $
#$Revision: 198224 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/85/7228594.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_7228594
loop_
_publ_author_name
'Goswami, Pramod Kumar'
'Kumar, Vineet'
'Thaimattam, Ram'
'Ramanan , A.'
_publ_section_title
;
 Structural landscape of multicomponent solids of 5-aminosalicylic acid
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01008G
_journal_year                    2017
_chemical_formula_moiety         'C7 H6 N O3, 0.5(C4 H12 N2)'
_chemical_formula_sum            'C9 H12 N2 O3'
_chemical_formula_weight         196.21
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'SHELXTL-NT2000 ver.6.12'
_audit_update_record
;
2017-06-24 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.731(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5529(10)
_cell_length_b                   17.206(3)
_cell_length_c                   8.5190(13)
_cell_measurement_reflns_used    2022
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.81
_cell_measurement_theta_min      2.37
_cell_volume                     936.9(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8881
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         2.722
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.401
_exptl_crystal_size_mid          0.318
_exptl_crystal_size_min          0.225
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1643
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.210
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0767
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0622P)²+0.9645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1696
_refine_ls_wR_factor_ref         0.1748
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1484
_reflns_number_total             1643
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce01008g2.cif
_cod_data_source_block           solid6
_cod_database_code               7228594
_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O -0.0886(4) 0.60242(15) 0.3240(3) 0.0557(8) Uani 1 1 d . .
O2 O 0.1778(4) 0.52323(14) 0.3330(3) 0.0540(7) Uani 1 1 d . .
O3 O -0.0662(3) 0.71954(14) 0.5004(3) 0.0479(7) Uani 1 1 d . .
H3 H -0.1215 0.6877 0.4327 0.072 Uiso 1 1 calc R U
N1 N 0.6831(4) 0.54563(15) 0.0601(3) 0.0383(7) Uani 1 1 d . .
H1A H 0.7001 0.5704 -0.0279 0.046 Uiso 1 1 calc R U
H1B H 0.7847 0.5608 0.1419 0.046 Uiso 1 1 calc R U
N2 N 0.7478(4) 0.63267(15) 0.7888(3) 0.0389(7) Uani 1 1 d . .
H2A H 0.8006 0.5905 0.7609 0.047 Uiso 1 1 calc R U
H2B H 0.8189 0.6608 0.8650 0.047 Uiso 1 1 calc R U
C1 C 0.0982(5) 0.58016(18) 0.3819(3) 0.0347(7) Uani 1 1 d . .
C2 C 0.2204(4) 0.62965(16) 0.5151(3) 0.0290(7) Uani 1 1 d . .
C3 C 0.4273(4) 0.61162(16) 0.5865(3) 0.0303(7) Uani 1 1 d . .
H6 H 0.4888 0.5684 0.5504 0.036 Uiso 1 1 calc R U
C4 C 0.5439(4) 0.65587(17) 0.7092(3) 0.0302(7) Uani 1 1 d . .
C5 C 0.4507(5) 0.72052(18) 0.7617(4) 0.0395(8) Uani 1 1 d . .
H7 H 0.5258 0.7507 0.8454 0.047 Uiso 1 1 calc R U
C6 C 0.2484(5) 0.74014(18) 0.6908(4) 0.0400(8) Uani 1 1 d . .
H8 H 0.1887 0.7838 0.7270 0.048 Uiso 1 1 calc R U
C7 C 0.1314(5) 0.69658(17) 0.5670(3) 0.0327(7) Uani 1 1 d . .
C8 C 0.4778(5) 0.5671(2) 0.0936(4) 0.0428(8) Uani 1 1 d . .
H10A H 0.4698 0.6232 0.1025 0.051 Uiso 1 1 calc R U
H9B H 0.4657 0.5448 0.1957 0.051 Uiso 1 1 calc R U
C9 C 0.7003(5) 0.46089(18) 0.0365(4) 0.0382(8) Uani 1 1 d . .
H11A H 0.6985 0.4340 0.1362 0.046 Uiso 1 1 calc R U
H12B H 0.8320 0.4493 0.0072 0.046 Uiso 1 1 calc R U
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_site_symmetry_1
_geom_angle_site_symmetry_3
C7 O3 H3 109.5 . .
C9 N1 C8 111.8(2) . .
C9 N1 H1A 109.3 . .
C8 N1 H1A 109.3 . .
C9 N1 H1B 109.3 . .
C8 N1 H1B 109.3 . .
H1A N1 H1B 107.9 . .
C4 N2 H2A 120.0 . .
C4 N2 H2B 120.0 . .
H2A N2 H2B 120.0 . .
O2 C1 O1 123.6(3) . .
O2 C1 C2 121.0(3) . .
O1 C1 C2 115.4(3) . .
C3 C2 C7 118.5(3) . .
C3 C2 C1 120.6(3) . .
C7 C2 C1 120.9(3) . .
C4 C3 C2 122.1(3) . .
C4 C3 H6 119.0 . .
C2 C3 H6 119.0 . .
C3 C4 C5 118.4(3) . .
C3 C4 N2 120.9(3) . .
C5 C4 N2 120.5(3) . .
C6 C5 C4 120.4(3) . .
C6 C5 H7 119.8 . .
C4 C5 H7 119.8 . .
C5 C6 C7 121.5(3) . .
C5 C6 H8 119.2 . .
C7 C6 H8 119.2 . .
O3 C7 C6 118.7(3) . .
O3 C7 C2 122.2(3) . .
C6 C7 C2 119.1(3) . .
N1 C8 C9 111.6(3) . 3_665
N1 C8 H10A 109.3 . .
C9 C8 H10A 109.3 3_665 .
N1 C8 H9B 109.3 . .
C9 C8 H9B 109.3 3_665 .
H10A C8 H9B 108.0 . .
N1 C9 C8 110.3(3) . 3_665
N1 C9 H11A 109.6 . .
C8 C9 H11A 109.6 3_665 .
N1 C9 H12B 109.6 . .
C8 C9 H12B 109.6 3_665 .
H11A C9 H12B 108.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.273(4) .
O2 C1 1.225(4) .
O3 C7 1.353(4) .
O3 H3 0.8200 .
N1 C9 1.480(4) .
N1 C8 1.482(4) .
N1 H1A 0.8900 .
N1 H1B 0.8900 .
N2 C4 1.416(4) .
N2 H2A 0.8600 .
N2 H2B 0.8600 .
C1 C2 1.501(4) .
C2 C3 1.393(4) .
C2 C7 1.405(4) .
C3 C4 1.380(4) .
C3 H6 0.9300 .
C4 C5 1.390(4) .
C5 C6 1.372(4) .
C5 H7 0.9300 .
C6 C7 1.381(4) .
C6 H8 0.9300 .
C8 C9 1.501(4) 3_665
C8 H10A 0.9700 .
C8 H9B 0.9700 .
C9 C8 1.501(4) 3_665
C9 H11A 0.9700 .
C9 H12B 0.9700 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H9B O2 0.97 2.46 3.219(4) 135.2 .
N2 H2B O3 0.86 2.40 3.199(3) 155.0 4_676
N2 H2A O2 0.86 2.13 2.955(4) 160.6 3_666
N1 H1B O1 0.89 1.74 2.601(3) 160.8 1_655
N1 H1A N2 0.89 1.98 2.863(4) 175.2 1_554
O3 H3 O1 0.82 1.77 2.499(3) 146.6 .
O3 H3 O1 0.82 1.77 2.499(3) 146.6 .
N1 H1A N2 0.89 1.98 2.863(4) 175.2 1_554
N1 H1B O1 0.89 1.74 2.601(3) 160.8 1_655
N2 H2A O2 0.86 2.13 2.955(4) 160.6 3_666
N2 H2B O3 0.86 2.40 3.199(3) 155.0 4_676
C8 H9B O2 0.97 2.46 3.219(4) 135.2 .
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
_geom_torsion_site_symmetry_4
O2 C1 C2 C3 -0.3(4) .
O1 C1 C2 C3 -179.2(3) .
O2 C1 C2 C7 177.6(3) .
O1 C1 C2 C7 -1.3(4) .
C7 C2 C3 C4 2.1(4) .
C1 C2 C3 C4 -180.0(3) .
C2 C3 C4 C5 -0.3(4) .
C2 C3 C4 N2 174.6(3) .
C3 C4 C5 C6 -1.0(4) .
N2 C4 C5 C6 -176.0(3) .
C4 C5 C6 C7 0.4(5) .
C5 C6 C7 O3 -179.1(3) .
C5 C6 C7 C2 1.5(5) .
C3 C2 C7 O3 177.9(3) .
C1 C2 C7 O3 0.0(4) .
C3 C2 C7 C6 -2.7(4) .
C1 C2 C7 C6 179.4(3) .
C9 N1 C8 C9 -55.9(4) 3_665
C8 N1 C9 C8 55.1(4) 3_665
