#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/26/2202647.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_2202647
loop_
_publ_author_name
'Zeller, Matthias'
'Hunter, Allen D.'
'Perrine, Cynthia L.'
_publ_section_title
;
 p-Diisocyanotetramethylbenzene
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1655
_journal_page_last               o1656
_journal_paper_doi               10.1107/S1600536803020087
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C12 H12 N2'
_chemical_formula_sum            'C12 H12 N2'
_chemical_formula_weight         184.24
_chemical_name_common            '1,4-bisisocyano-2,3,5,6-tetramethyl benzene'
_chemical_name_systematic        '1,4-bisisocyano-2,3,5,6-tetramethyl benzene'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 112.010(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.1518(17)
_cell_length_b                   5.1324(5)
_cell_length_c                   12.3670(12)
_cell_measurement_reflns_used    4202
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3175
_cell_measurement_theta_min      2.5615
_cell_volume                     1009.32(17)
_computing_cell_refinement       'SAINT-Plus (Bruker 1997-1999)'
_computing_data_collection       'SMART (Bruker 1997-2000)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4935
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         3.52
_diffrn_standards_decay_%        stable
_diffrn_standards_number         no
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.268
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     69
_refine_ls_number_reflns         1257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0698P)²+0.6662P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1312
_reflns_number_gt                1181
_reflns_number_total             1257
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            fl6059.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      'C 2/c'
_cod_database_code               2202647
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_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 0.35731(5) 1.04662(17) 0.68084(7) 0.0217(3) Uani d . 1 . . N
C3 0.33877(6) 0.71435(19) 0.53560(8) 0.0190(3) Uani d . 1 . . C
C4 0.28404(6) 0.56146(19) 0.44509(8) 0.0189(3) Uani d . 1 . . C
C1 0.40179(7) 1.1675(2) 0.75919(9) 0.0288(3) Uani d . 1 . . C
C2 0.30288(6) 0.89616(19) 0.58851(8) 0.0188(3) Uani d . 1 . . C
C5 0.43300(6) 0.6884(2) 0.57347(9) 0.0245(3) Uani d . 1 . . C
H5A 0.4605 0.8340 0.6249 0.037 Uiso calc PR 0.899(16) . . H
H5B 0.4483 0.6906 0.5047 0.037 Uiso calc PR 0.899(16) . . H
H5C 0.4513 0.5237 0.6155 0.037 Uiso calc PR 0.899(16) . . H
H5D 0.4462 0.5315 0.5385 0.037 Uiso calc PR 0.101(16) . . H
H5E 0.4585 0.6749 0.6587 0.037 Uiso calc PR 0.101(16) . . H
H5F 0.4555 0.8418 0.5479 0.037 Uiso calc PR 0.101(16) . . H
C6 0.31677(6) 0.3562(2) 0.38534(9) 0.0242(3) Uani d . 1 . . C
H6A 0.2740 0.2207 0.3533 0.036 Uiso calc PR 0.721(16) . . H
H6B 0.3680 0.2782 0.4419 0.036 Uiso calc PR 0.721(16) . . H
H6C 0.3296 0.4365 0.3220 0.036 Uiso calc PR 0.721(16) . . H
H6D 0.3737 0.4029 0.3915 0.036 Uiso calc PR 0.279(16) . . H
H6E 0.2797 0.3454 0.3029 0.036 Uiso calc PR 0.279(16) . . H
H6F 0.3181 0.1872 0.4228 0.036 Uiso calc PR 0.279(16) . . H
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 0.0224(4) 0.0249(5) 0.0205(4) -0.0007(3) 0.0111(3) -0.0005(3)
C3 0.0198(5) 0.0224(5) 0.0175(4) 0.0016(3) 0.0100(4) 0.0030(3)
C4 0.0220(5) 0.0204(5) 0.0179(5) 0.0014(3) 0.0114(4) 0.0018(3)
C1 0.0261(5) 0.0349(6) 0.0265(5) -0.0015(4) 0.0110(4) -0.0056(4)
C2 0.0211(5) 0.0212(5) 0.0160(4) -0.0010(3) 0.0091(3) 0.0006(3)
C5 0.0193(5) 0.0319(6) 0.0237(5) 0.0022(4) 0.0096(4) -0.0003(4)
C6 0.0277(5) 0.0248(5) 0.0257(5) 0.0021(4) 0.0163(4) -0.0022(4)
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
_geom_angle_publ_flag
C1 N1 C2 . . 178.30(10) yes
C4 C3 C2 . . 117.65(9) yes
C4 C3 C5 . . 121.14(8) yes
C2 C3 C5 . . 121.20(9) yes
C3 C4 C2 . 7_566 117.92(9) yes
C3 C4 C6 . . 121.39(8) yes
C2 C4 C6 7_566 . 120.69(9) yes
N1 C2 C4 . 7_566 117.59(8) yes
N1 C2 C3 . . 117.99(8) yes
C4 C2 C3 7_566 . 124.42(9) yes
C3 C5 H5A . . 109.5 no
C3 C5 H5B . . 109.5 no
H5A C5 H5B . . 109.5 no
C3 C5 H5C . . 109.5 no
H5A C5 H5C . . 109.5 no
H5B C5 H5C . . 109.5 no
C3 C5 H5D . . 109.5 no
H5A C5 H5D . . 141.1 no
H5B C5 H5D . . 56.3 no
H5C C5 H5D . . 56.3 no
C3 C5 H5E . . 109.5 no
H5A C5 H5E . . 56.3 no
H5B C5 H5E . . 141.1 no
H5C C5 H5E . . 56.3 no
H5D C5 H5E . . 109.5 no
C3 C5 H5F . . 109.5 no
H5A C5 H5F . . 56.3 no
H5B C5 H5F . . 56.3 no
H5C C5 H5F . . 141.1 no
H5D C5 H5F . . 109.5 no
H5E C5 H5F . . 109.5 no
C4 C6 H6A . . 109.5 no
C4 C6 H6B . . 109.5 no
H6A C6 H6B . . 109.5 no
C4 C6 H6C . . 109.5 no
H6A C6 H6C . . 109.5 no
H6B C6 H6C . . 109.5 no
C4 C6 H6D . . 109.5 no
H6A C6 H6D . . 141.1 no
H6B C6 H6D . . 56.3 no
H6C C6 H6D . . 56.3 no
C4 C6 H6E . . 109.5 no
H6A C6 H6E . . 56.3 no
H6B C6 H6E . . 141.1 no
H6C C6 H6E . . 56.3 no
H6D C6 H6E . . 109.5 no
C4 C6 H6F . . 109.5 no
H6A C6 H6F . . 56.3 no
H6B C6 H6F . . 56.3 no
H6C C6 H6F . . 141.1 no
H6D C6 H6F . . 109.5 no
H6E C6 H6F . . 109.5 no
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 C1 . 1.1628(14) yes
N1 C2 . 1.4045(12) yes
C3 C4 . 1.4008(13) yes
C3 C2 . 1.4070(13) yes
C3 C5 . 1.5106(13) yes
C4 C6 . 1.5105(13) yes
C2 C4 7_566 1.4065(13) yes
C5 H5A . 0.9800 no
C5 H5B . 0.9800 no
C5 H5C . 0.9800 no
C5 H5D . 0.9800 no
C5 H5E . 0.9800 no
C5 H5F . 0.9800 no
C6 H6A . 0.9800 no
C6 H6B . 0.9800 no
C6 H6C . 0.9800 no
C6 H6D . 0.9800 no
C6 H6E . 0.9800 no
C6 H6F . 0.9800 no
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_4
_geom_torsion
_geom_torsion_publ_flag
C2 C3 C4 C2 7_566 1.38(15) no
C5 C3 C4 C2 7_566 -177.49(8) no
C2 C3 C4 C6 . -178.34(8) no
C5 C3 C4 C6 . 2.79(14) no
C4 C3 C2 N1 . 178.78(8) no
C5 C3 C2 N1 . -2.35(14) no
C4 C3 C2 C4 7_566 -1.48(16) no
C5 C3 C2 C4 7_566 177.39(9) no
