#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/39/2013980.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_2013980
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-decylphenyl isocyanide
;
_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                 91.130(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.6642(12)
_cell_length_b                   7.831(2)
_cell_length_c                   20.607(5)
_cell_measurement_reflns_used    985
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.6
_cell_volume                     752.5(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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.024
_diffrn_reflns_av_sigmaI/netI    0.026
_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            6459
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        'less than 1'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS; Sheldrick, 2002; Blessing, 1995
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.074
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.065
_refine_ls_R_factor_gt           0.038
_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)+(0.054P)²+0.023P] where
P=(Fo²+2Fc²)/3'
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.098
_refine_ls_wR_factor_ref         0.106
_reflns_number_gt                1190
_reflns_number_total             1827
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fr1469.cif
_cod_data_source_block           I
_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               2013980
_cod_database_fobs_code          2013980
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
C1 0.0163(4) 0.2500 1.03516(8) 0.0444(4) Uani d S 1 . . C
N2 0.1757(3) 0.2500 0.99256(6) 0.0348(3) Uani d S 1 . . N
C3 0.3717(3) 0.2500 0.94150(6) 0.0301(4) Uani d S 1 . . C
C4 0.4675(2) 0.40436(15) 0.91720(5) 0.0333(3) Uani d . 1 . . C
H4 0.394(2) 0.5105(15) 0.9357(4) 0.034(3) Uiso d . 1 . . H
C5 0.6616(2) 0.40270(15) 0.86747(5) 0.0326(3) Uani d . 1 . . C
H5 0.727(2) 0.5103(16) 0.8499(5) 0.039(3) Uiso d . 1 . . H
C6 0.7598(3) 0.2500 0.84119(6) 0.0300(4) Uani d S 1 . . C
C7 0.9508(3) 0.2500 0.78310(7) 0.0343(4) Uani d S 1 . . C
H7 1.076(2) 0.3521(14) 0.7848(5) 0.039(3) Uiso d . 1 . . H
C8 0.7741(3) 0.2500 0.71951(7) 0.0313(4) Uani d S 1 . . C
H8 0.646(2) 0.3515(14) 0.7196(5) 0.037(3) Uiso d . 1 . . H
C9 0.9539(3) 0.2500 0.65875(7) 0.0311(4) Uani d S 1 . . C
H9 1.084(2) 0.3516(14) 0.6590(5) 0.037(3) Uiso d . 1 . . H
C10 0.7736(3) 0.2500 0.59617(7) 0.0324(4) Uani d S 1 . . C
H10 0.643(2) 0.3508(15) 0.5956(5) 0.040(3) Uiso d . 1 . . H
C11 0.9507(3) 0.2500 0.53483(7) 0.0322(4) Uani d S 1 . . C
H11 1.082(2) 0.3521(14) 0.5353(5) 0.039(3) Uiso d . 1 . . H
C12 0.7700(3) 0.2500 0.47233(7) 0.0332(4) Uani d S 1 . . C
H12 0.642(2) 0.3518(15) 0.4721(5) 0.041(3) Uiso d . 1 . . H
C13 0.9488(3) 0.2500 0.41132(7) 0.0322(4) Uani d S 1 . . C
H13 1.079(2) 0.3508(14) 0.4115(5) 0.036(3) Uiso d . 1 . . H
C14 0.7697(3) 0.2500 0.34850(7) 0.0330(4) Uani d S 1 . . C
H14 0.638(2) 0.3502(14) 0.3480(5) 0.038(3) Uiso d . 1 . . H
C15 0.9467(3) 0.2500 0.28737(7) 0.0346(4) Uani d S 1 . . C
H15 1.078(2) 0.3515(14) 0.2881(5) 0.041(3) Uiso d . 1 . . H
C16 0.7633(4) 0.2500 0.22568(8) 0.0461(5) Uani d S 1 . . C
H16B 0.635(3) 0.3539(17) 0.2245(6) 0.066(4) Uiso d . 1 . . H
H16A 0.881(4) 0.2500 0.1867(9) 0.053(5) Uiso d S 1 . . 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
C1 N2 C3 . . 179.30(15)
C4 C3 C4 . 4_565 121.45(14)
C4 C3 N2 . . 119.27(7)
C4 C3 N2 4_565 . 119.27(7)
C5 C4 C3 . . 118.73(11)
C5 C4 H4 . . 122.4(6)
C3 C4 H4 . . 118.9(6)
C4 C5 C6 . . 121.45(12)
C4 C5 H5 . . 119.1(6)
C6 C5 H5 . . 119.4(6)
C5 C6 C5 4_565 . 118.16(14)
C5 C6 C7 4_565 . 120.86(7)
C5 C6 C7 . . 120.86(7)
C6 C7 C8 . . 111.27(12)
C6 C7 H7 . . 109.2(6)
C8 C7 H7 . . 109.6(6)
C9 C8 C7 . . 114.05(12)
C9 C8 H8 . . 110.0(6)
C7 C8 H8 . . 108.2(6)
C8 C9 C10 . . 113.09(12)
C8 C9 H9 . . 109.9(6)
C10 C9 H9 . . 109.2(6)
C11 C10 C9 . . 113.74(13)
C11 C10 H10 . . 109.4(6)
C9 C10 H10 . . 109.6(6)
C10 C11 C12 . . 113.64(13)
C10 C11 H11 . . 109.4(6)
C12 C11 H11 . . 109.5(6)
C13 C12 C11 . . 113.25(13)
C13 C12 H12 . . 109.5(6)
C11 C12 H12 . . 108.9(6)
C12 C13 C14 . . 113.61(13)
C12 C13 H13 . . 109.9(6)
C14 C13 H13 . . 109.1(6)
C15 C14 C13 . . 113.93(13)
C15 C14 H14 . . 109.6(6)
C13 C14 H14 . . 109.6(6)
C16 C15 C14 . . 112.83(14)
C16 C15 H15 . . 110.3(6)
C14 C15 H15 . . 109.2(6)
C15 C16 H16B . . 110.1(7)
C15 C16 H16A . . 111.8(10)
H7 C7 H7 4_565 . 107.8(9)
H8 C8 H8 4_565 . 106.1(9)
H9 C9 H9 4_565 . 105.3(9)
H10 C10 H10 4_565 . 104.7(9)
H11 C11 H11 4_565 . 105.2(9)
H12 C12 H12 4_565 . 106.5(9)
H13 C13 H13 4_565 . 104.9(9)
H14 C14 H14 4_565 . 104.0(9)
H15 C15 H15 4_565 . 104.8(9)
H16B C16 H16B 4_565 . 107.4(9)
H16B C16 H16A . . 108.6(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
C1 N2 . 1.1616(18) ?
N2 C3 . 1.4072(18) ?
C3 C4 . 1.3858(13) ?
C3 C4 4_565 1.3858(13) ?
C4 C5 . 1.3808(15) ?
C4 H4 . 0.979(11) ?
C5 C6 . 1.3939(13) ?
C5 H5 . 0.969(12) ?
C6 C5 4_565 1.3939(13) ?
C6 C7 . 1.506(2) ?
C7 C8 . 1.5342(19) ?
C7 H7 . 0.989(11) ?
C8 C9 . 1.521(2) ?
C8 H8 . 0.995(11) ?
C9 C10 . 1.5255(19) ?
C9 H9 . 1.001(11) ?
C10 C11 . 1.523(2) ?
C10 H10 . 0.997(11) ?
C11 C12 . 1.5252(19) ?
C11 H11 . 1.007(11) ?
C12 C13 . 1.523(2) ?
C12 H12 . 0.995(11) ?
C13 C14 . 1.527(2) ?
C13 H13 . 0.995(11) ?
C14 C15 . 1.520(2) ?
C14 H14 . 0.996(11) ?
C15 C16 . 1.518(2) ?
C15 H15 . 1.003(11) ?
C16 H16B . 1.009(13) ?
C16 H16A . 0.979(18) ?
