#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/45/2234572.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_2234572
loop_
_publ_author_name
'Ge, Chunhua'
'Zhang, Rui'
'Zhang, Xiangdong'
'Zhang, Chenglong'
'Zhang, Meiyin'
_publ_section_title
;
 N-(3-Hydroxyphenyl)nicotinamide
;
_journal_coeditor_code           CV5281
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1499
_journal_paper_doi               10.1107/S1600536812015620
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C12 H10 N2 O2'
_chemical_formula_moiety         'C12 H10 N2 O2'
_chemical_formula_sum            'C12 H10 N2 O2'
_chemical_formula_weight         214.22
_chemical_name_systematic
;
N-(3-Hydroxyphenyl)nicotinamide
;
_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                 94.428(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1741(13)
_cell_length_b                   5.2613(6)
_cell_length_c                   15.3113(16)
_cell_measurement_reflns_used    82
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.31
_cell_measurement_theta_min      2.23
_cell_volume                     977.79(18)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω 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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5813
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1928
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0396
_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)+(0.0441P)²+0.3178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                1572
_reflns_number_total             1928
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5281.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2234572
_cod_database_fobs_code          2234572
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_symmetry_multiplicity
O O2 0.10112(9) 0.0774(2) 0.89614(8) 0.0393(3) Uani d . 1 1
H H2B 0.1369 -0.0179 0.9298 0.059 Uiso calc R 1 1
N N2 0.46607(10) 0.4089(3) 0.86950(8) 0.0293(3) Uani d . 1 1
C C12 0.28388(12) 0.2438(3) 0.88031(10) 0.0289(3) Uani d . 1 1
H H12 0.3155 0.1113 0.9137 0.035 Uiso calc R 1 1
O O1 0.51225(9) 0.8283(2) 0.87911(8) 0.0403(3) Uani d . 1 1
C C5 0.73908(12) 0.6822(3) 0.88082(10) 0.0309(4) Uani d . 1 1
H H5 0.7221 0.8299 0.8493 0.037 Uiso calc R 1 1
N N1 0.79027(10) 0.2474(3) 0.97897(9) 0.0327(3) Uani d . 1 1
C C11 0.17038(12) 0.2524(3) 0.86264(10) 0.0310(4) Uani d . 1 1
C C6 0.53822(12) 0.6020(3) 0.88392(10) 0.0279(3) Uani d . 1 1
C C2 0.86888(13) 0.3961(3) 0.95025(10) 0.0339(4) Uani d . 1 1
H H2 0.9420 0.3493 0.9632 0.041 Uiso calc R 1 1
C C9 0.19122(13) 0.6308(3) 0.77876(10) 0.0354(4) Uani d . 1 1
H H9 0.1596 0.7605 0.7441 0.042 Uiso calc R 1 1
C C8 0.30484(13) 0.6289(3) 0.79759(10) 0.0310(4) Uani d . 1 1
H H8 0.3490 0.7560 0.7767 0.037 Uiso calc R 1 1
C C4 0.65565(12) 0.5257(3) 0.90684(9) 0.0267(3) Uani d . 1 1
C C7 0.35048(12) 0.4310(3) 0.84863(9) 0.0267(3) Uani d . 1 1
C C1 0.84752(13) 0.6154(3) 0.90241(11) 0.0349(4) Uani d . 1 1
H H1 0.9048 0.7159 0.8851 0.042 Uiso calc R 1 1
C C3 0.68548(12) 0.3122(3) 0.95639(10) 0.0307(4) Uani d . 1 1
H H3 0.6298 0.2087 0.9749 0.037 Uiso calc R 1 1
C C10 0.12390(13) 0.4454(3) 0.81013(10) 0.0349(4) Uani d . 1 1
H H10 0.0482 0.4501 0.7962 0.042 Uiso calc R 1 1
H H2A 0.4898(13) 0.261(4) 0.8741(10) 0.030(5) Uiso d . 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O2 0.0341(6) 0.0315(7) 0.0528(8) 0.0008(5) 0.0074(5) 0.0036(5)
N2 0.0292(7) 0.0198(7) 0.0385(8) 0.0021(6) -0.0012(5) 0.0000(6)
C12 0.0318(8) 0.0221(8) 0.0323(8) 0.0038(6) -0.0013(6) -0.0014(6)
O1 0.0347(6) 0.0231(6) 0.0624(8) 0.0011(5) -0.0004(5) -0.0003(5)
C5 0.0350(8) 0.0266(8) 0.0311(8) -0.0025(7) 0.0027(6) 0.0010(6)
N1 0.0306(7) 0.0273(7) 0.0396(7) 0.0001(6) -0.0012(6) -0.0012(6)
C11 0.0303(8) 0.0270(8) 0.0360(8) -0.0001(7) 0.0037(6) -0.0074(7)
C6 0.0301(8) 0.0238(8) 0.0298(8) 0.0004(6) 0.0027(6) -0.0003(6)
C2 0.0276(8) 0.0333(9) 0.0402(9) 0.0008(7) -0.0006(7) -0.0051(7)
C9 0.0422(9) 0.0320(9) 0.0311(8) 0.0121(8) -0.0025(7) -0.0001(7)
C8 0.0366(8) 0.0268(8) 0.0294(8) 0.0010(7) 0.0007(6) -0.0011(6)
C4 0.0299(8) 0.0228(8) 0.0274(7) 0.0000(6) 0.0023(6) -0.0049(6)
C7 0.0283(7) 0.0229(8) 0.0284(7) 0.0021(6) -0.0002(6) -0.0044(6)
C1 0.0301(8) 0.0372(9) 0.0381(9) -0.0065(7) 0.0062(7) -0.0026(7)
C3 0.0295(8) 0.0266(8) 0.0360(8) -0.0034(6) 0.0021(6) -0.0018(7)
C10 0.0289(8) 0.0383(10) 0.0370(9) 0.0070(7) -0.0010(7) -0.0069(7)
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
C11 O2 H2B 109.5
C6 N2 C7 126.48(14)
C6 N2 H2A 118.2(12)
C7 N2 H2A 115.3(11)
C7 C12 C11 120.56(14)
C7 C12 H12 119.7
C11 C12 H12 119.7
C1 C5 C4 119.16(15)
C1 C5 H5 120.4
C4 C5 H5 120.4
C2 N1 C3 117.27(14)
O2 C11 C12 122.38(14)
O2 C11 C10 118.15(14)
C12 C11 C10 119.47(14)
O1 C6 N2 123.82(14)
O1 C6 C4 120.52(14)
N2 C6 C4 115.67(13)
N1 C2 C1 123.60(15)
N1 C2 H2 118.2
C1 C2 H2 118.2
C10 C9 C8 121.96(15)
C10 C9 H9 119.0
C8 C9 H9 119.0
C9 C8 C7 117.99(15)
C9 C8 H8 121.0
C7 C8 H8 121.0
C3 C4 C5 118.02(14)
C3 C4 C6 123.28(13)
C5 C4 C6 118.62(14)
C12 C7 C8 120.59(14)
C12 C7 N2 117.24(13)
C8 C7 N2 122.16(14)
C2 C1 C5 118.47(15)
C2 C1 H1 120.8
C5 C1 H1 120.8
N1 C3 C4 123.40(14)
N1 C3 H3 118.3
C4 C3 H3 118.3
C9 C10 C11 119.38(14)
C9 C10 H10 120.3
C11 C10 H10 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C11 1.3741(19)
O2 H2B 0.8200
N2 C6 1.350(2)
N2 C7 1.4234(19)
N2 H2A 0.831(18)
C12 C7 1.387(2)
C12 C11 1.388(2)
C12 H12 0.9300
O1 C6 1.2325(18)
C5 C1 1.381(2)
C5 C4 1.389(2)
C5 H5 0.9300
N1 C2 1.336(2)
N1 C3 1.3396(19)
C11 C10 1.388(2)
C6 C4 1.500(2)
C2 C1 1.381(2)
C2 H2 0.9300
C9 C10 1.384(2)
C9 C8 1.391(2)
C9 H9 0.9300
C8 C7 1.391(2)
C8 H8 0.9300
C4 C3 1.388(2)
C1 H1 0.9300
C3 H3 0.9300
C10 H10 0.9300
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
_geom_hbond_publ_flag
O2 H2B N1 3_657 0.82 2.00 2.817(2) 173 yes
N2 H2A O1 1_545 0.83(2) 2.29(2) 3.107(2) 166 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 589712
