#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/39/2013981.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_2013981
loop_
_publ_author_name
'Britton, Doyle'
'Sowa Jr, John R.'
'Mann, Kent R.'
_publ_section_title
;
 p-Decylphenyl isocyanide and p-decylbenzonitrile:
 isomorphous isonitrile/nitrile isomers
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o418
_journal_page_last               o420
_journal_paper_doi               10.1107/S0108270104008388
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C17 H25 N'
_chemical_formula_moiety         'C17 H25 N'
_chemical_formula_sum            'C17 H25 N'
_chemical_formula_weight         243.38
_chemical_name_systematic
;
p-decylbenzonitrile
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.500(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.6526(12)
_cell_length_b                   7.801(2)
_cell_length_c                   20.466(5)
_cell_measurement_reflns_used    1019
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.8
_cell_volume                     742.8(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
;
 Siemens SMART area-detector
;
_diffrn_measurement_method       '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  0.070
_diffrn_reflns_av_sigmaI/netI    0.066
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8715
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        'less than 1'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.088
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.16
_refine_ls_extinction_coef       0.053(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   0.74
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         1812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.74
_refine_ls_R_factor_all          0.128
_refine_ls_R_factor_gt           0.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 calc w=1/[σ²(Fo²)+(0.104P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.093
_refine_ls_wR_factor_ref         0.107
_reflns_number_gt                918
_reflns_number_total             1812
_reflns_threshold_expression     'I>2σ(I) '
_cod_data_source_file            fr1469.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2013981
_cod_database_fobs_code          2013981
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_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
_atom_site_type_symbol
N1 -0.0006(5) 0.2500 1.04131(9) 0.0530(6) Uani d S 1 . . N
C2 0.1548(5) 0.2500 0.99777(11) 0.0400(6) Uani d S 1 . . C
C3 0.3533(5) 0.2500 0.94377(9) 0.0339(6) Uani d S 1 . . C
C4 0.4504(3) 0.4039(2) 0.91927(6) 0.0387(5) Uani d . 1 . . C
H4A 0.3839 0.5093 0.9368 0.046 Uiso calc R 1 . . H
C5 0.6463(3) 0.4027(2) 0.86865(6) 0.0381(5) Uani d . 1 . . C
H5A 0.7144 0.5083 0.8516 0.046 Uiso calc R 1 . . H
C6 0.7443(4) 0.2500 0.84258(9) 0.0329(6) Uani d S 1 . . C
C7 0.9381(5) 0.2500 0.78401(8) 0.0390(6) Uani d S 1 . . C
H7A 1.0630 0.1473 0.7854 0.047 Uiso calc PR 0.50 . . H
H7B 1.0630 0.3527 0.7854 0.047 Uiso calc PR 0.50 . . H
C8 0.7625(5) 0.2500 0.72056(8) 0.0368(6) Uani d S 1 . . C
H8A 0.6370 0.1475 0.7199 0.044 Uiso calc PR 0.50 . . H
H8B 0.6370 0.3525 0.7199 0.044 Uiso calc PR 0.50 . . H
C9 0.9458(5) 0.2500 0.65944(9) 0.0351(6) Uani d S 1 . . C
H9A 1.0712 0.3525 0.6600 0.042 Uiso calc PR 0.50 . . H
H9B 1.0712 0.1475 0.6600 0.042 Uiso calc PR 0.50 . . H
C10 0.7683(5) 0.2500 0.59677(9) 0.0375(6) Uani d S 1 . . C
H10A 0.6428 0.1475 0.5964 0.045 Uiso calc PR 0.50 . . H
H10B 0.6428 0.3525 0.5964 0.045 Uiso calc PR 0.50 . . H
C11 0.9478(5) 0.2500 0.53518(9) 0.0363(6) Uani d S 1 . . C
H11A 1.0733 0.1475 0.5355 0.044 Uiso calc PR 0.50 . . H
H11B 1.0733 0.3525 0.5355 0.044 Uiso calc PR 0.50 . . H
C12 0.7700(5) 0.2500 0.47260(9) 0.0373(6) Uani d S 1 . . C
H12A 0.6445 0.1475 0.4721 0.045 Uiso calc PR 0.50 . . H
H12B 0.6445 0.3525 0.4721 0.045 Uiso calc PR 0.50 . . H
C13 0.9527(5) 0.2500 0.41105(8) 0.0370(6) Uani d S 1 . . C
H13A 1.0781 0.3525 0.4115 0.044 Uiso calc PR 0.50 . . H
H13B 1.0781 0.1475 0.4115 0.044 Uiso calc PR 0.50 . . H
C14 0.7750(5) 0.2500 0.34829(8) 0.0361(6) Uani d S 1 . . C
H14A 0.6495 0.1475 0.3478 0.043 Uiso calc PR 0.50 . . H
H14B 0.6495 0.3525 0.3478 0.043 Uiso calc PR 0.50 . . H
C15 0.9561(5) 0.2500 0.28701(9) 0.0397(6) Uani d S 1 . . C
H15A 1.0814 0.1475 0.2873 0.048 Uiso calc PR 0.50 . . H
H15B 1.0814 0.3525 0.2873 0.048 Uiso calc PR 0.50 . . H
C16 0.7753(5) 0.2500 0.22464(9) 0.0520(7) Uani d S 1 . . C
H16A 0.9021 0.2500 0.1866 0.078 Uiso calc SR 1 . . H
H16B 0.6538 0.3526 0.2236 0.078 Uiso calc PR 0.50 . . H
H16C 0.6538 0.1474 0.2236 0.078 Uiso calc PR 0.50 . . H
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'
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
N1 C2 C3 . . 179.2(2)
C4 C3 C4 . 4_565 121.1(2)
C4 C3 C2 . . 119.42(10)
C4 C3 C2 4_565 . 119.42(10)
C5 C4 C3 . . 119.04(17)
C5 C4 H4A . . 120.5
C3 C4 H4A . . 120.5
C4 C5 C6 . . 121.00(17)
C4 C5 H5A . . 119.5
C6 C5 H5A . . 119.5
C5 C6 C5 4_565 . 118.8(2)
C5 C6 C7 4_565 . 120.54(10)
C5 C6 C7 . . 120.54(10)
C6 C7 C8 . . 110.93(17)
C6 C7 H7A . . 109.5
C8 C7 H7A . . 109.5
C6 C7 H7B . . 109.5
C8 C7 H7B . . 109.5
H7A C7 H7B . . 108.0
C9 C8 C7 . . 113.55(18)
C9 C8 H8A . . 108.9
C7 C8 H8A . . 108.9
C9 C8 H8B . . 108.9
C7 C8 H8B . . 108.9
H8A C8 H8B . . 107.7
C10 C9 C8 . . 112.94(17)
C10 C9 H9A . . 109.0
C8 C9 H9A . . 109.0
C10 C9 H9B . . 109.0
C8 C9 H9B . . 109.0
H9A C9 H9B . . 107.8
C11 C10 C9 . . 113.70(17)
C11 C10 H10A . . 108.8
C9 C10 H10A . . 108.8
C11 C10 H10B . . 108.8
C9 C10 H10B . . 108.8
H10A C10 H10B . . 107.7
C10 C11 C12 . . 113.61(17)
C10 C11 H11A . . 108.8
C12 C11 H11A . . 108.8
C10 C11 H11B . . 108.8
C12 C11 H11B . . 108.8
H11A C11 H11B . . 107.7
C13 C12 C11 . . 113.13(17)
C13 C12 H12A . . 109.0
C11 C12 H12A . . 109.0
C13 C12 H12B . . 109.0
C11 C12 H12B . . 109.0
H12A C12 H12B . . 107.8
C14 C13 C12 . . 113.24(18)
C14 C13 H13A . . 108.9
C12 C13 H13A . . 108.9
C14 C13 H13B . . 108.9
C12 C13 H13B . . 108.9
H13A C13 H13B . . 107.7
C15 C14 C13 . . 113.36(17)
C15 C14 H14A . . 108.9
C13 C14 H14A . . 108.9
C15 C14 H14B . . 108.9
C13 C14 H14B . . 108.9
H14A C14 H14B . . 107.7
C14 C15 C16 . . 112.74(18)
C14 C15 H15A . . 109.0
C16 C15 H15A . . 109.0
C14 C15 H15B . . 109.0
C16 C15 H15B . . 109.0
H15A C15 H15B . . 107.8
C15 C16 H16A . . 109.5
C15 C16 H16B . . 109.5
H16A C16 H16B . . 109.5
C15 C16 H16C . . 109.5
H16A C16 H16C . . 109.5
H16B C16 H16C . . 109.5
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
N1 C2 . 1.153(2) ?
C2 C3 . 1.446(3) ?
C3 C4 . 1.3789(17) ?
C3 C4 4_565 1.3789(17) ?
C4 C5 . 1.3860(19) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.3842(17) ?
C5 H5A . 0.9500 ?
C6 C5 4_565 1.3842(17) ?
C6 C7 . 1.506(3) ?
C7 C8 . 1.528(3) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C9 . 1.520(2) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.519(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.518(2) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.519(2) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.526(2) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C14 . 1.521(3) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.517(2) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.522(3) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
