#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/54/2235410.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_2235410
loop_
_publ_author_name
'Burnham, Lauren E.'
'Gano, Katrina J.'
'Young, Amber M.'
'Risley, John M.'
'Jones, Daniel S.'
_publ_section_title
;
 N-(4-Isocyanophenyl)succinamic acid
;
_journal_coeditor_code           FJ2512
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2078
_journal_paper_doi               10.1107/S1600536812025226
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H10 N2 O3'
_chemical_formula_moiety         'C11 H10 N2 O3'
_chemical_formula_sum            'C11 H10 N2 O3'
_chemical_formula_weight         218.21
_chemical_name_systematic
;
N-(4-Isocyanophenyl)succinamic acid
;
_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           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 94.771(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0974(2)
_cell_length_b                   16.2774(7)
_cell_length_c                   12.5674(6)
_cell_measurement_reflns_used    2647
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      66.8489
_cell_measurement_theta_min      3.5262
_cell_volume                     1039.13(8)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2011)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2011)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2011)
;
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 1997) and Mercury (Macrae et
al., 2006)
;
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_detector_area_resol_mean 10.4419
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Agilent Xcalibur Atlas Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54182
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7543
_diffrn_reflns_theta_full        66.96
_diffrn_reflns_theta_max         66.96
_diffrn_reflns_theta_min         4.45
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.74566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2011)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.246
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0476P)²+0.2570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                1527
_reflns_number_total             1839
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            fj2512.cif
_cod_data_source_block           I
_cod_database_code               2235410
_cod_database_fobs_code          2235410
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
H HN2 -0.184(4) 0.6215(11) 0.6545(15) 0.028(5) Uiso d . 1
H HO3 0.484(5) 0.4256(16) 0.9999(19) 0.064(7) Uiso d . 1
O O3 0.3472(2) 0.40108(7) 0.95600(10) 0.0327(3) Uani d . 1
O O2 0.2537(2) 0.53307(7) 0.92254(10) 0.0307(3) Uani d . 1
O O1 0.2238(2) 0.48805(7) 0.66450(9) 0.0302(3) Uani d . 1
N N2 -0.0524(3) 0.59719(8) 0.63180(11) 0.0246(3) Uani d . 1
N N1 0.4162(3) 0.77295(8) 0.31697(11) 0.0286(3) Uani d . 1
C C4 -0.0207(3) 0.71789(10) 0.52404(13) 0.0254(4) Uani d . 1
H H4 -0.1583 0.7404 0.5585 0.03 Uiso calc R 1
C C7 0.3901(3) 0.65037(10) 0.42199(13) 0.0261(4) Uani d . 1
H H7 0.5285 0.6283 0.3875 0.031 Uiso calc R 1
C C2 0.2966(3) 0.72819(10) 0.39560(12) 0.0248(4) Uani d . 1
C C6 0.2774(3) 0.60562(10) 0.49959(13) 0.0254(4) Uani d . 1
H H6 0.339 0.5531 0.517 0.03 Uiso calc R 1
C C3 0.0902(3) 0.76253(10) 0.44606(13) 0.0268(4) Uani d . 1
H H3 0.028 0.8147 0.4275 0.032 Uiso calc R 1
C C8 0.0281(3) 0.52704(10) 0.68370(13) 0.0246(4) Uani d . 1
C C9 -0.1502(3) 0.49859(10) 0.76713(13) 0.0269(4) Uani d . 1
H H9A -0.3155 0.4793 0.7321 0.032 Uiso calc R 1
H H9B -0.188 0.5445 0.8127 0.032 Uiso calc R 1
C C5 0.0710(3) 0.63904(9) 0.55200(12) 0.0234(3) Uani d . 1
C C11 0.2059(3) 0.46016(10) 0.90780(13) 0.0256(4) Uani d . 1
C C1 0.5262(4) 0.80691(11) 0.25313(15) 0.0351(4) Uani d . 1
C C10 -0.0224(3) 0.43002(10) 0.83482(14) 0.0281(4) Uani d . 1
H H10C -0.1525 0.4056 0.8772 0.034 Uiso calc R 1
H H10D 0.0385 0.3877 0.7884 0.034 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 O3 HO3 108.1(15)
C8 N2 C5 127.90(14)
C8 N2 HN2 116.4(12)
C5 N2 HN2 115.4(12)
C1 N1 C2 176.27(17)
C3 C4 C5 120.89(14)
C3 C4 H4 119.6
C5 C4 H4 119.6
C6 C7 C2 119.82(14)
C6 C7 H7 120.1
C2 C7 H7 120.1
C7 C2 C3 121.15(15)
C7 C2 N1 118.79(14)
C3 C2 N1 120.06(14)
C7 C6 C5 120.10(15)
C7 C6 H6 119.9
C5 C6 H6 119.9
C4 C3 C2 118.89(15)
C4 C3 H3 120.6
C2 C3 H3 120.6
O1 C8 N2 123.98(15)
O1 C8 C9 121.58(15)
N2 C8 C9 114.42(14)
C8 C9 C10 111.00(13)
C8 C9 H9A 109.4
C10 C9 H9A 109.4
C8 C9 H9B 109.4
C10 C9 H9B 109.4
H9A C9 H9B 108
C6 C5 C4 119.16(14)
C6 C5 N2 123.20(14)
C4 C5 N2 117.64(13)
O2 C11 O3 122.96(15)
O2 C11 C10 122.95(15)
O3 C11 C10 114.08(14)
C11 C10 C9 112.13(13)
C11 C10 H10C 109.2
C9 C10 H10C 109.2
C11 C10 H10D 109.2
C9 C10 H10D 109.2
H10C C10 H10D 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C11 1.318(2)
O3 HO3 0.94(3)
O2 C11 1.2226(19)
O1 C8 1.2235(19)
N2 C8 1.361(2)
N2 C5 1.404(2)
N2 HN2 0.85(2)
N1 C1 1.157(2)
N1 C2 1.407(2)
C4 C3 1.378(2)
C4 C5 1.401(2)
C4 H4 0.93
C7 C6 1.380(2)
C7 C2 1.384(2)
C7 H7 0.93
C2 C3 1.390(2)
C6 C5 1.397(2)
C6 H6 0.93
C3 H3 0.93
C8 C9 1.516(2)
C9 C10 1.517(2)
C9 H9A 0.97
C9 H9B 0.97
C11 C10 1.503(2)
C10 H10C 0.97
C10 H10D 0.97
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
O3 HO3 O2 3_667 0.94(3) 1.72(3) 2.6646(17) 177(2)
