#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/96/2219630.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_2219630
loop_
_publ_author_name
'Zhuang, Yu-Guo'
'Jiang, Hua-Jiang'
'Hong, Zhi'
'Qiu, Fang-Li'
_publ_section_title
;
 N-Phenylpyridine-2-carbamide
;
_journal_coeditor_code           IM2083
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1904
_journal_paper_doi               10.1107/S1600536808028274
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C12 H10 N2 O'
_chemical_formula_moiety         'C12 H10 N2 O'
_chemical_formula_sum            'C12 H10 N2 O'
_chemical_formula_weight         198.22
_chemical_name_systematic
;
N-Phenylpyridine-2-carbamide
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.752(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.7469(2)
_cell_length_b                   6.2382(2)
_cell_length_c                   14.0158(3)
_cell_measurement_reflns_used    2226
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      2.9
_cell_volume                     500.74(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia,1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5000
_diffrn_reflns_theta_full        27.66
_diffrn_reflns_theta_max         27.66
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0300
_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)+(0.0365P)²+0.0548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0749
_reflns_number_gt                1036
_reflns_number_total             1162
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2083.cif
_cod_data_source_block           I
_cod_database_code               2219630
_cod_database_fobs_code          2219630
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, 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
N N1 -0.0173(3) 0.2086(3) 0.59409(11) 0.0452(4) Uani d . 1
H H101 -0.1420 0.2510 0.6183 0.054 Uiso calc R 1
C C8 0.1414(3) 0.5113(3) 0.68241(13) 0.0435(4) Uani d . 1
C C6 -0.0401(3) 0.0235(3) 0.53631(12) 0.0412(4) Uani d . 1
C C1 0.1246(4) -0.0375(4) 0.47407(15) 0.0509(5) Uani d . 1
H H1 0.2570 0.0459 0.4685 0.061 Uiso calc R 1
C C7 0.1751(4) 0.3270(3) 0.61595(15) 0.0475(5) Uani d . 1
C C2 0.0901(4) -0.2230(4) 0.42049(16) 0.0569(5) Uani d . 1
H H2 0.1999 -0.2635 0.3787 0.068 Uiso calc R 1
N N2 -0.0537(3) 0.5139(3) 0.72828(12) 0.0526(4) Uani d . 1
C C5 -0.2373(4) -0.1016(3) 0.54213(15) 0.0476(5) Uani d . 1
H H5 -0.3507 -0.0595 0.5819 0.057 Uiso calc R 1
O O1 0.3656(3) 0.2937(3) 0.58575(15) 0.0753(6) Uani d . 1
C C10 0.2767(5) 0.8384(3) 0.75234(17) 0.0575(5) Uani d . 1
H H10 0.3863 0.9481 0.7597 0.069 Uiso calc R 1
C C11 0.0794(4) 0.8441(4) 0.80026(16) 0.0612(6) Uani d . 1
H H11 0.0523 0.9575 0.8410 0.073 Uiso calc R 1
C C3 -0.1044(4) -0.3483(4) 0.42826(16) 0.0553(5) Uani d . 1
H H3 -0.1255 -0.4731 0.3923 0.066 Uiso calc R 1
C C12 -0.0787(4) 0.6788(4) 0.78711(17) 0.0629(6) Uani d . 1
H H12 -0.2107 0.6823 0.8213 0.076 Uiso calc R 1
C C9 0.3106(4) 0.6677(3) 0.69302(15) 0.0516(5) Uani d . 1
H H9 0.4451 0.6581 0.6607 0.062 Uiso calc R 1
C C4 -0.2676(4) -0.2879(4) 0.48961(17) 0.0553(5) Uani d . 1
H H4 -0.3986 -0.3728 0.4956 0.066 Uiso calc R 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
N1 0.0458(9) 0.0397(9) 0.0515(9) -0.0007(7) 0.0121(7) -0.0031(7)
C8 0.0478(10) 0.0408(10) 0.0422(10) 0.0013(8) 0.0051(8) 0.0021(8)
C6 0.0458(10) 0.0369(10) 0.0408(10) 0.0030(8) 0.0042(8) 0.0021(8)
C1 0.0504(11) 0.0521(12) 0.0517(11) -0.0041(10) 0.0120(9) -0.0028(10)
C7 0.0497(11) 0.0398(11) 0.0539(12) -0.0030(9) 0.0092(9) -0.0007(9)
C2 0.0594(13) 0.0609(14) 0.0515(12) 0.0060(11) 0.0117(9) -0.0103(10)
N2 0.0477(9) 0.0540(10) 0.0566(10) -0.0015(8) 0.0067(8) -0.0096(8)
C5 0.0464(10) 0.0458(11) 0.0515(10) -0.0004(9) 0.0088(8) -0.0024(9)
O1 0.0531(9) 0.0669(11) 0.1095(15) -0.0111(9) 0.0283(9) -0.0330(10)
C10 0.0699(14) 0.0471(11) 0.0550(11) -0.0102(12) 0.0014(10) -0.0007(11)
C11 0.0714(16) 0.0553(14) 0.0559(13) 0.0065(12) -0.0002(11) -0.0156(11)
C3 0.0652(13) 0.0459(11) 0.0537(11) 0.0014(11) -0.0023(10) -0.0119(10)
C12 0.0561(13) 0.0705(15) 0.0635(14) 0.0047(11) 0.0122(11) -0.0168(12)
C9 0.0559(11) 0.0486(12) 0.0513(11) -0.0086(10) 0.0116(9) -0.0018(9)
C4 0.0550(12) 0.0506(13) 0.0598(12) -0.0070(10) 0.0027(10) -0.0027(11)
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C7 N1 C6 128.07(17)
C7 N1 H101 116.0
C6 N1 H101 116.0
N2 C8 C9 123.48(19)
N2 C8 C7 117.62(17)
C9 C8 C7 118.89(18)
C5 C6 C1 119.06(17)
C5 C6 N1 117.74(17)
C1 C6 N1 123.19(17)
C2 C1 C6 119.57(19)
C2 C1 H1 120.2
C6 C1 H1 120.2
O1 C7 N1 124.81(19)
O1 C7 C8 120.61(18)
N1 C7 C8 114.58(18)
C3 C2 C1 120.8(2)
C3 C2 H2 119.6
C1 C2 H2 119.6
C12 N2 C8 116.38(18)
C4 C5 C6 120.77(19)
C4 C5 H5 119.6
C6 C5 H5 119.6
C11 C10 C9 118.9(2)
C11 C10 H10 120.6
C9 C10 H10 120.6
C10 C11 C12 118.7(2)
C10 C11 H11 120.7
C12 C11 H11 120.7
C2 C3 C4 119.6(2)
C2 C3 H3 120.2
C4 C3 H3 120.2
N2 C12 C11 123.8(2)
N2 C12 H12 118.1
C11 C12 H12 118.1
C10 C9 C8 118.7(2)
C10 C9 H9 120.6
C8 C9 H9 120.6
C3 C4 C5 120.1(2)
C3 C4 H4 119.9
C5 C4 H4 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.344(3)
N1 C6 1.410(2)
N1 H101 0.8600
C8 N2 1.338(2)
C8 C9 1.377(3)
C8 C7 1.502(3)
C6 C5 1.384(3)
C6 C1 1.392(3)
C1 C2 1.385(3)
C1 H1 0.9300
C7 O1 1.223(3)
C2 C3 1.376(4)
C2 H2 0.9300
N2 C12 1.333(3)
C5 C4 1.379(3)
C5 H5 0.9300
C10 C11 1.365(4)
C10 C9 1.375(3)
C10 H10 0.9300
C11 C12 1.377(3)
C11 H11 0.9300
C3 C4 1.377(3)
C3 H3 0.9300
C12 H12 0.9300
C9 H9 0.9300
C4 H4 0.9300
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_publ_flag
N1 H101 N2 0.86 2.28 2.697(2) 110.0 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5383604
