#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/93/2209367.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_2209367
loop_
_publ_author_name
'Shao-Min Shi'
'Bing Jia'
'Yu Wu'
'Xiao-Dong Liu'
'Zong-Qiu Hu'
_publ_section_title
;
 Phenyl 2-picolinamidobenzoate
;
_journal_coeditor_code           YM2001
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2278
_journal_page_last               o2280
_journal_paper_doi               10.1107/S1600536806016382
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C19 H14 N2 O3'
_chemical_formula_moiety         'C19 H14 N2 O3'
_chemical_formula_sum            'C19 H14 N2 O3'
_chemical_formula_weight         318.32
_chemical_name_systematic
;
Phenyl 2-nicotinamidobenzoate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.910(8)
_cell_angle_beta                 97.291(9)
_cell_angle_gamma                96.008(7)
_cell_formula_units_Z            2
_cell_length_a                   5.657(2)
_cell_length_b                   11.700(4)
_cell_length_c                   11.793(4)
_cell_measurement_reflns_used    1525
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      1.7
_cell_volume                     758.7(5)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material
'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      292(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method       ω
_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  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0604
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8013
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         1.7
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.91
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.91
_refine_ls_R_factor_all          0.078
_refine_ls_R_factor_gt           0.048
_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)+(0.0404P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.088
_refine_ls_wR_factor_ref         0.100
_reflns_number_gt                1895
_reflns_number_total             2965
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ym2001.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2209367
_cod_database_fobs_code          2209367
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O O2 0.5737(2) 0.77499(11) 0.08049(10) 0.0550(4) Uani d . 1
O O1 0.2550(2) 0.64053(11) 0.06645(10) 0.0562(4) Uani d . 1
O O3 1.1388(2) 0.89121(12) 0.45048(11) 0.0658(4) Uani d . 1
N N1 0.8591(2) 0.83152(12) 0.28852(11) 0.0445(4) Uani d . 1
H H1B 0.8314 0.8381 0.2166 0.053 Uiso calc R 1
N N2 1.1266(3) 0.95815(13) 0.16759(12) 0.0491(4) Uani d . 1
C C1 0.0137(3) 0.69998(17) -0.08912(16) 0.0552(5) Uani d . 1
H H1A -0.0710 0.7388 -0.0358 0.066 Uiso calc R 1
C C2 -0.0474(3) 0.69855(17) -0.20690(17) 0.0576(5) Uani d . 1
H H2A -0.1731 0.7376 -0.2330 0.069 Uiso calc R 1
C C3 0.0760(3) 0.64012(16) -0.28502(16) 0.0518(5) Uani d . 1
H H3A 0.0333 0.6390 -0.3640 0.062 Uiso calc R 1
C C4 0.2623(4) 0.58332(16) -0.24673(16) 0.0552(5) Uani d . 1
H H4A 0.3458 0.5436 -0.3000 0.066 Uiso calc R 1
C C5 0.3269(3) 0.58463(15) -0.12995(16) 0.0525(5) Uani d . 1
H H5A 0.4538 0.5464 -0.1037 0.063 Uiso calc R 1
C C6 0.2004(3) 0.64334(15) -0.05317(15) 0.0445(4) Uani d . 1
C C7 0.4492(3) 0.71242(15) 0.12722(14) 0.0410(4) Uani d . 1
C C8 0.4817(3) 0.70152(14) 0.25079(14) 0.0386(4) Uani d . 1
C C9 0.3088(3) 0.63207(15) 0.29266(15) 0.0471(5) Uani d . 1
H H9A 0.1756 0.5930 0.2418 0.056 Uiso calc R 1
C C10 0.3304(4) 0.62008(16) 0.40706(15) 0.0554(5) Uani d . 1
H H10A 0.2133 0.5735 0.4337 0.066 Uiso calc R 1
C C11 0.5280(4) 0.67786(17) 0.48205(16) 0.0603(6) Uani d . 1
H H11A 0.5434 0.6701 0.5599 0.072 Uiso calc R 1
C C12 0.7026(3) 0.74675(16) 0.44408(15) 0.0549(5) Uani d . 1
H H12A 0.8349 0.7846 0.4963 0.066 Uiso calc R 1
C C13 0.6839(3) 0.76068(14) 0.32821(14) 0.0406(4) Uani d . 1
C C14 1.0681(3) 0.89158(15) 0.34899(15) 0.0440(4) Uani d . 1
C C15 1.2137(3) 0.96070(14) 0.27886(14) 0.0418(4) Uani d . 1
C C16 1.2623(3) 1.02017(17) 0.10772(16) 0.0560(5) Uani d . 1
H H16A 1.2050 1.0204 0.0303 0.067 Uiso calc R 1
C C17 1.4809(3) 1.08338(16) 0.15369(16) 0.0557(5) Uani d . 1
H H17A 1.5678 1.1255 0.1085 0.067 Uiso calc R 1
C C18 1.5680(3) 1.08327(16) 0.26667(17) 0.0572(5) Uani d . 1
H H18A 1.7166 1.1244 0.2999 0.069 Uiso calc R 1
C C19 1.4315(3) 1.02104(16) 0.33077(16) 0.0529(5) Uani d . 1
H H19A 1.4863 1.0199 0.4083 0.063 Uiso calc R 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
_geom_angle_publ_flag
C7 O1 C6 117.79(13) y
C14 N1 C13 128.46(14) y
C14 N1 H1B 115.8 ?
C13 N1 H1B 115.8 ?
C15 N2 C16 116.32(16) ?
C6 C1 C2 118.54(18) ?
C6 C1 H1A 120.7 ?
C2 C1 H1A 120.7 ?
C3 C2 C1 120.43(19) ?
C3 C2 H2A 119.8 ?
C1 C2 H2A 119.8 ?
C2 C3 C4 119.91(18) ?
C2 C3 H3A 120.0 ?
C4 C3 H3A 120.0 ?
C3 C4 C5 120.47(18) ?
C3 C4 H4A 119.8 ?
C5 C4 H4A 119.8 ?
C6 C5 C4 118.68(18) ?
C6 C5 H5A 120.7 ?
C4 C5 H5A 120.7 ?
C1 C6 C5 121.96(17) ?
C1 C6 O1 118.34(16) ?
C5 C6 O1 119.62(17) ?
O2 C7 O1 121.33(15) ?
O2 C7 C8 126.91(16) ?
O1 C7 C8 111.76(14) ?
C9 C8 C13 119.16(15) ?
C9 C8 C7 119.44(16) ?
C13 C8 C7 121.40(15) ?
C10 C9 C8 121.49(17) ?
C10 C9 H9A 119.3 ?
C8 C9 H9A 119.3 ?
C9 C10 C11 119.07(17) ?
C9 C10 H10A 120.5 ?
C11 C10 H10A 120.5 ?
C12 C11 C10 121.18(17) ?
C12 C11 H11A 119.4 ?
C10 C11 H11A 119.4 ?
C11 C12 C13 120.78(18) ?
C11 C12 H12A 119.6 ?
C13 C12 H12A 119.6 ?
C12 C13 N1 121.42(16) ?
C12 C13 C8 118.32(16) ?
N1 C13 C8 120.27(15) ?
O3 C14 N1 125.03(17) ?
O3 C14 C15 120.68(16) ?
N1 C14 C15 114.29(15) ?
N2 C15 C19 123.10(16) ?
N2 C15 C14 118.07(15) ?
C19 C15 C14 118.81(16) ?
N2 C16 C17 124.00(18) ?
N2 C16 H16A 118.0 ?
C17 C16 H16A 118.0 ?
C18 C17 C16 118.70(18) ?
C18 C17 H17A 120.7 ?
C16 C17 H17A 120.7 ?
C17 C18 C19 118.64(18) ?
C17 C18 H18A 120.7 ?
C19 C18 H18A 120.7 ?
C15 C19 C18 119.24(18) ?
C15 C19 H19A 120.4 ?
C18 C19 H19A 120.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O2 C7 1.2046(18) ?
O1 C7 1.3593(19) ?
O1 C6 1.412(2) y
O3 C14 1.2137(19) ?
N1 C14 1.363(2) y
N1 C13 1.398(2) ?
N1 H1B 0.8600 ?
N2 C15 1.337(2) ?
N2 C16 1.340(2) ?
C1 C6 1.362(2) ?
C1 C2 1.385(2) ?
C1 H1A 0.9300 ?
C2 C3 1.368(2) ?
C2 H2A 0.9300 ?
C3 C4 1.370(2) ?
C3 H3A 0.9300 ?
C4 C5 1.377(2) ?
C4 H4A 0.9300 ?
C5 C6 1.370(2) ?
C5 H5A 0.9300 ?
C7 C8 1.472(2) ?
C8 C9 1.393(2) ?
C8 C13 1.412(2) ?
C9 C10 1.369(2) ?
C9 H9A 0.9300 ?
C10 C11 1.376(3) ?
C10 H10A 0.9300 ?
C11 C12 1.372(3) ?
C11 H11A 0.9300 ?
C12 C13 1.393(2) ?
C12 H12A 0.9300 ?
C14 C15 1.503(2) ?
C15 C19 1.372(2) ?
C16 C17 1.373(3) ?
C16 H16A 0.9300 ?
C17 C18 1.361(2) ?
C17 H17A 0.9300 ?
C18 C19 1.378(2) ?
C18 H18A 0.9300 ?
C19 H19A 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
N1 H1B O2 1_555 0.86 2.02 2.708(2) 137 yes
N1 H1B N2 1_555 0.86 2.26 2.693(2) 111 yes
C9 H9A O1 1_555 0.93 2.31 2.665(2) 102 no
C12 H12A O3 1_555 0.93 2.19 2.827(2) 125 no
C19 H19A O3 2_876 0.93 2.54 3.269(2) 133 yes
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_publ_flag
C6 C1 C2 C3 0.8(3) ?
C1 C2 C3 C4 -0.5(3) ?
C2 C3 C4 C5 -0.1(3) ?
C3 C4 C5 C6 0.3(3) ?
C2 C1 C6 C5 -0.6(3) ?
C2 C1 C6 O1 -177.17(16) ?
C4 C5 C6 C1 0.1(3) ?
C4 C5 C6 O1 176.58(15) ?
C7 O1 C6 C1 -103.79(19) y
C7 O1 C6 C5 79.6(2) ?
C6 O1 C7 O2 -1.4(2) ?
C6 O1 C7 C8 179.06(14) y
O2 C7 C8 C9 174.51(17) ?
O1 C7 C8 C9 -6.0(2) ?
O2 C7 C8 C13 -5.0(3) ?
O1 C7 C8 C13 174.50(15) ?
C13 C8 C9 C10 0.1(3) ?
C7 C8 C9 C10 -179.47(16) ?
C8 C9 C10 C11 -0.1(3) ?
C9 C10 C11 C12 -0.1(3) ?
C10 C11 C12 C13 0.4(3) ?
C11 C12 C13 N1 179.33(17) ?
C11 C12 C13 C8 -0.4(3) ?
C14 N1 C13 C12 2.7(3) ?
C14 N1 C13 C8 -177.59(16) ?
C9 C8 C13 C12 0.2(2) ?
C7 C8 C13 C12 179.74(15) ?
C9 C8 C13 N1 -179.56(15) ?
C7 C8 C13 N1 0.0(2) ?
C13 N1 C14 O3 1.3(3) y
C13 N1 C14 C15 -179.28(14) y
C16 N2 C15 C19 -1.1(3) ?
C16 N2 C15 C14 -179.53(15) ?
O3 C14 C15 N2 -179.80(16) ?
N1 C14 C15 N2 0.7(2) ?
O3 C14 C15 C19 1.7(3) ?
N1 C14 C15 C19 -177.75(15) ?
C15 N2 C16 C17 0.6(3) ?
N2 C16 C17 C18 0.4(3) ?
C16 C17 C18 C19 -0.9(3) ?
N2 C15 C19 C18 0.6(3) ?
C14 C15 C19 C18 179.05(16) ?
C17 C18 C19 C15 0.4(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128063
