#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/24/2222435.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_2222435
loop_
_publ_author_name
'Gowda, B. Thimme'
'Foro, Sabine'
'Fuess, Hartmut'
_publ_section_title
;
 N-Phenylformamide
;
_journal_coeditor_code           RK2151
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1633
_journal_paper_doi               10.1107/S1600536809022776
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C7 H7 N O'
_chemical_formula_moiety         'C7 H7 N O'
_chemical_formula_sum            'C7 H7 N O'
_chemical_formula_weight         121.14
_chemical_name_systematic
;
N-Phenylformamide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 113.140(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   30.923(3)
_cell_length_b                   6.1737(6)
_cell_length_c                   14.8140(10)
_cell_measurement_reflns_used    2475
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.66
_cell_volume                     2600.6(4)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method       'ω and φ'
_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  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8394
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.76
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9691
_exptl_absorpt_correction_T_min  0.9657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.099
_refine_ls_extinction_coef       0.0028(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2383
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0368
_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)+(0.0651P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                1679
_reflns_number_total             2383
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2151.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2222435
_cod_database_fobs_code          2222435
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_disorder_assembly
_atom_site_disorder_group
O O1 0.09999(4) 0.21410(18) 0.62537(8) 0.0921(4) Uani d . 1 . .
N N1 0.04841(4) 0.34831(19) 0.47961(9) 0.0694(4) Uani d . 1 . .
H H1N 0.0202(6) 0.322(2) 0.4332(11) 0.083 Uiso d . 1 . .
C C1 0.07229(4) 0.5289(2) 0.46365(9) 0.0561(3) Uani d . 1 . .
C C2 0.04734(5) 0.6657(3) 0.38753(10) 0.0727(4) Uani d . 1 . .
H H2 0.0159 0.6367 0.3491 0.087 Uiso calc R 1 . .
C C3 0.06857(6) 0.8441(3) 0.36825(12) 0.0893(5) Uani d . 1 . .
H H3 0.0515 0.9351 0.3164 0.107 Uiso calc R 1 . .
C C4 0.11462(6) 0.8895(3) 0.42461(12) 0.0890(5) Uani d . 1 . .
H H4 0.1289 1.0119 0.4119 0.107 Uiso calc R 1 . .
C C5 0.13948(6) 0.7535(3) 0.49972(12) 0.0828(5) Uani d . 1 . .
H H5 0.1709 0.7834 0.5378 0.099 Uiso calc R 1 . .
C C6 0.11890(5) 0.5734(2) 0.51989(11) 0.0687(4) Uani d . 1 . .
H H6 0.1363 0.4818 0.5712 0.082 Uiso calc R 1 . .
C C7 0.06296(6) 0.2094(2) 0.55435(12) 0.0792(5) Uani d . 1 . .
H H7 0.0426 0.0966 0.5518 0.095 Uiso calc R 1 . .
O O2 0.04140(4) 0.2563(2) 0.16582(9) 0.0996(4) Uani d . 1 . .
N N2 0.11861(4) 0.1904(2) 0.22825(8) 0.0628(3) Uani d . 1 . .
H H2N 0.1131(5) 0.067(3) 0.1994(10) 0.075 Uiso d . 1 . .
C C8 0.16640(5) 0.2389(2) 0.28235(9) 0.0565(3) Uani d . 1 . .
C C9 0.18179(6) 0.4299(3) 0.33258(13) 0.0862(5) Uani d . 1 . .
H H9 0.1603 0.5369 0.3309 0.103 Uiso calc R 1 . .
C C10 0.22921(7) 0.4618(3) 0.38543(14) 0.1024(6) Uani d . 1 . .
H H10 0.2394 0.5901 0.4202 0.123 Uiso calc R 1 . .
C C11 0.26131(6) 0.3093(3) 0.38760(14) 0.0963(6) Uani d . 1 . .
H H11 0.2932 0.3324 0.4235 0.116 Uiso calc R 1 . .
C C12 0.24605(6) 0.1230(3) 0.33668(13) 0.0919(5) Uani d . 1 . .
H H12 0.2678 0.0184 0.3371 0.110 Uiso calc R 1 . .
C C13 0.19895(5) 0.0867(2) 0.28451(11) 0.0750(4) Uani d . 1 . .
H H13 0.1891 -0.0425 0.2503 0.090 Uiso calc R 1 . .
C C14 0.08175(6) 0.3109(3) 0.21441(12) 0.0771(4) Uani d . 1 . .
H H14 0.0867 0.4471 0.2436 0.093 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C1 . . 128.45(13) ?
C7 N1 H1N . . 115.8(10) ?
C1 N1 H1N . . 115.7(10) ?
C2 C1 C6 . . 119.24(13) ?
C2 C1 N1 . . 117.46(12) ?
C6 C1 N1 . . 123.29(12) ?
C3 C2 C1 . . 120.27(14) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C4 C3 C2 . . 120.51(15) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C5 C4 C3 . . 119.30(15) ?
C5 C4 H4 . . 120.4 ?
C3 C4 H4 . . 120.4 ?
C4 C5 C6 . . 121.06(15) ?
C4 C5 H5 . . 119.5 ?
C6 C5 H5 . . 119.5 ?
C5 C6 C1 . . 119.62(14) ?
C5 C6 H6 . . 120.2 ?
C1 C6 H6 . . 120.2 ?
O1 C7 N1 . . 126.94(14) ?
O1 C7 H7 . . 116.5 ?
N1 C7 H7 . . 116.5 ?
C14 N2 C8 . . 128.51(14) ?
C14 N2 H2N . . 115.9(10) ?
C8 N2 H2N . . 115.6(10) ?
C13 C8 C9 . . 118.76(14) ?
C13 C8 N2 . . 117.69(12) ?
C9 C8 N2 . . 123.55(13) ?
C8 C9 C10 . . 119.64(16) ?
C8 C9 H9 . . 120.2 ?
C10 C9 H9 . . 120.2 ?
C11 C10 C9 . . 121.22(17) ?
C11 C10 H10 . . 119.4 ?
C9 C10 H10 . . 119.4 ?
C12 C11 C10 . . 118.93(17) ?
C12 C11 H11 . . 120.5 ?
C10 C11 H11 . . 120.5 ?
C11 C12 C13 . . 120.85(17) ?
C11 C12 H12 . . 119.6 ?
C13 C12 H12 . . 119.6 ?
C8 C13 C12 . . 120.59(15) ?
C8 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
O2 C14 N2 . . 124.22(16) ?
O2 C14 H14 . . 117.9 ?
N2 C14 H14 . . 117.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.2132(17) ?
N1 C7 . 1.3314(19) ?
N1 C1 . 1.4076(17) ?
N1 H1N . 0.888(16) ?
C1 C2 . 1.3771(19) ?
C1 C6 . 1.3797(18) ?
C2 C3 . 1.369(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.367(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.365(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.371(2) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
O2 C14 . 1.2178(18) ?
N2 C14 . 1.3082(19) ?
N2 C8 . 1.4089(17) ?
N2 H2N . 0.857(16) ?
C8 C13 . 1.3684(19) ?
C8 C9 . 1.375(2) ?
C9 C10 . 1.378(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.359(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.354(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.373(2) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 H14 . 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
N1 H1N O2 2 0.888(16) 1.936(16) 2.8239(17) 178.1(14)
N2 H2N O1 6 0.857(16) 2.007(16) 2.8637(17) 177.0(14)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C1 C2 . . . . -171.26(15) ?
C7 N1 C1 C6 . . . . 9.0(2) ?
C6 C1 C2 C3 . . . . -0.2(2) ?
N1 C1 C2 C3 . . . . 180.00(14) ?
C1 C2 C3 C4 . . . . -0.5(3) ?
C2 C3 C4 C5 . . . . 0.8(3) ?
C3 C4 C5 C6 . . . . -0.5(3) ?
C4 C5 C6 C1 . . . . -0.2(2) ?
C2 C1 C6 C5 . . . . 0.5(2) ?
N1 C1 C6 C5 . . . . -179.70(14) ?
C1 N1 C7 O1 . . . . 1.5(3) ?
C14 N2 C8 C13 . . . . -178.73(14) ?
C14 N2 C8 C9 . . . . 1.3(2) ?
C13 C8 C9 C10 . . . . -1.4(2) ?
N2 C8 C9 C10 . . . . 178.58(15) ?
C8 C9 C10 C11 . . . . 1.1(3) ?
C9 C10 C11 C12 . . . . 0.0(3) ?
C10 C11 C12 C13 . . . . -0.8(3) ?
C9 C8 C13 C12 . . . . 0.7(2) ?
N2 C8 C13 C12 . . . . -179.34(13) ?
C11 C12 C13 C8 . . . . 0.4(3) ?
C8 N2 C14 O2 . . . . 179.62(13) ?
