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#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/98/1519837.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_1519837
loop_
_publ_author_name
'Berry, D.'
'Blagden, N.'
'Coles, Simon J.'
'Hursthouse, Michael B.'
'Coles, Simon J.'
_publ_section_title
;
 2-Hydroxy-benzoic acid nicotinamide
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              295
_journal_year                    2007
_chemical_formula_sum            'C13 H12 N2 O4'
_chemical_formula_weight         260.25
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 97.5560(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0751(2)
_cell_length_b                   4.94410(10)
_cell_length_c                   22.8470(5)
_cell_measurement_reflns_used    3121
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1240.16(4)
_computing_cell_refinement       'DENZO, COLLECT'
_computing_data_reduction        'DENZO, COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'φ and 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  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18385
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9989
_exptl_absorpt_correction_T_min  0.9542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0542P)²+0.5739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1226
_reflns_number_gt                2214
_reflns_number_total             2853
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-295.cif
_cod_data_source_block           2007src0325
_cod_depositor_comments
;
Citation :
Berry, D and Blagden, N and Coles, Simon J. and Hursthouse, Michael B. and 
Coles, Simon J. (2007) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/295)

More at:
http://ecrystals.chem.soton.ac.uk/295/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1519837
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.00826(13) 1.0462(3) 0.28292(6) 0.0196(3) Uani 1 1 d . . .
C2 C 0.97753(13) 1.2578(3) 0.32436(6) 0.0198(3) Uani 1 1 d . . .
C3 C 1.06209(14) 1.3245(3) 0.37376(7) 0.0227(3) Uani 1 1 d . . .
C4 C 1.03362(16) 1.5208(4) 0.41354(7) 0.0291(4) Uani 1 1 d . . .
H4 H 1.0903 1.5644 0.4471 0.035 Uiso 1 1 calc R . .
C5 C 0.92264(16) 1.6515(4) 0.40391(8) 0.0325(4) Uani 1 1 d . . .
H5 H 0.9036 1.7857 0.4310 0.039 Uiso 1 1 calc R . .
C6 C 0.83812(16) 1.5891(4) 0.35495(8) 0.0307(4) Uani 1 1 d . . .
H6 H 0.7621 1.6808 0.3486 0.037 Uiso 1 1 calc R . .
C7 C 0.86587(14) 1.3929(3) 0.31573(7) 0.0249(3) Uani 1 1 d . . .
H7 H 0.8083 1.3494 0.2825 0.030 Uiso 1 1 calc R . .
O1 O 0.92465(9) 0.9936(2) 0.23870(5) 0.0232(3) Uani 1 1 d . . .
H1 H 0.9496 0.8719 0.2176 0.035 Uiso 1 1 calc R . .
O2 O 1.10869(10) 0.9304(2) 0.28991(5) 0.0259(3) Uani 1 1 d . . .
O3 O 1.17286(10) 1.2023(3) 0.38394(5) 0.0301(3) Uani 1 1 d . . .
H3 H 1.1788 1.0869 0.3575 0.045 Uiso 1 1 calc R . .
H2N H 0.7566(17) 0.397(4) -0.0351(9) 0.031(5) Uiso 1 1 d . . .
H1N H 0.8177(17) 0.623(4) 0.0093(8) 0.030(5) Uiso 1 1 d . . .
C8 C 0.86250(14) 0.2510(3) 0.03241(7) 0.0212(3) Uani 1 1 d . . .
C9 C 0.94553(14) 0.3305(3) 0.08699(6) 0.0200(3) Uani 1 1 d . . .
C10 C 0.91886(14) 0.5446(3) 0.12247(6) 0.0206(3) Uani 1 1 d . . .
H10 H 0.8472 0.6476 0.1110 0.025 Uiso 1 1 calc R . .
C11 C 1.09316(14) 0.4703(3) 0.18771(7) 0.0226(3) Uani 1 1 d . . .
H11 H 1.1452 0.5205 0.2224 0.027 Uiso 1 1 calc R . .
C12 C 1.12631(14) 0.2530(3) 0.15477(7) 0.0246(3) Uani 1 1 d . . .
H12 H 1.1993 0.1558 0.1668 0.029 Uiso 1 1 calc R . .
C13 C 1.05055(14) 0.1810(3) 0.10393(7) 0.0222(3) Uani 1 1 d . . .
H13 H 1.0702 0.0311 0.0810 0.027 Uiso 1 1 calc R . .
N1 N 0.99087(12) 0.6117(3) 0.17251(6) 0.0217(3) Uani 1 1 d . . .
N2 N 0.80259(13) 0.4487(3) 0.00129(6) 0.0270(3) Uani 1 1 d . . .
O4 O 0.85171(11) 0.0098(2) 0.01844(5) 0.0274(3) Uani 1 1 d . . .
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
O2 C1 O1 122.71(14) . .
O2 C1 C2 121.38(13) . .
O1 C1 C2 115.91(13) . .
C7 C2 C3 118.98(14) . .
C7 C2 C1 121.44(13) . .
C3 C2 C1 119.58(13) . .
O3 C3 C4 118.31(14) . .
O3 C3 C2 121.55(14) . .
C4 C3 C2 120.15(14) . .
C5 C4 C3 119.68(15) . .
C4 C5 C6 120.92(15) . .
C7 C6 C5 119.45(16) . .
C6 C7 C2 120.82(15) . .
O4 C8 N2 123.03(14) . .
O4 C8 C9 119.66(14) . .
N2 C8 C9 117.31(13) . .
C10 C9 C13 118.52(14) . .
C10 C9 C8 122.03(14) . .
C13 C9 C8 119.41(14) . .
N1 C10 C9 122.38(14) . .
N1 C11 C12 122.61(14) . .
C13 C12 C11 118.60(15) . .
C12 C13 C9 119.26(15) . .
C11 N1 C10 118.60(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O2 1.2424(18) .
C1 O1 1.3037(17) .
C1 C2 1.480(2) .
C2 C7 1.397(2) .
C2 C3 1.408(2) .
C3 O3 1.3597(19) .
C3 C4 1.394(2) .
C4 C5 1.380(2) .
C5 C6 1.395(3) .
C6 C7 1.383(2) .
C8 O4 1.2362(19) .
C8 N2 1.333(2) .
C8 C9 1.501(2) .
C9 C10 1.389(2) .
C9 C13 1.390(2) .
C10 N1 1.3465(19) .
C11 N1 1.338(2) .
C11 C12 1.388(2) .
C12 C13 1.387(2) .
