#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/13/2211306.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_2211306
loop_
_publ_author_name
'Li, Yin-Huai'
_publ_section_title
;
 6-tert-Butylnaphthalene-2,3-dicarbonitrile
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5935
_journal_page_last               o5936
_journal_paper_doi               10.1107/S1600536806050525
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C16 H14 N2'
_chemical_formula_sum            'C16 H14 N2'
_chemical_formula_weight         234.29
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1480(2)
_cell_length_b                   7.0072(2)
_cell_length_c                   16.7188(4)
_cell_measurement_reflns_used    1567
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.19
_cell_volume                     1306.01(5)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Smart CCD'
_diffrn_measurement_method       'ω scan'
_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  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10458
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_correction_T_min  0.9825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.141
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1399
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0364
_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)+(0.0615P)²+0.1377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                1062
_reflns_number_total             1399
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2213.cif
_cod_data_source_block           I
_cod_database_code               2211306
_cod_database_fobs_code          2211306
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
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
N N1 0.67990(15) 0.2500 0.27160(10) 0.0717(5) Uani d S 1
N N2 0.81811(14) 0.2500 0.48887(11) 0.0729(6) Uani d S 1
H H14B 0.1169 0.2500 0.7833 0.109 Uiso d SR 1
H H14A 0.2265 0.1420 0.7464 0.109 Uiso d R 1
C C1 0.61659(15) 0.2500 0.32500(10) 0.0501(5) Uani d S 1
C C2 0.71716(15) 0.2500 0.48083(10) 0.0482(4) Uani d S 1
C C3 0.53742(14) 0.2500 0.39309(9) 0.0404(4) Uani d S 1
C C4 0.58906(13) 0.2500 0.47134(9) 0.0391(4) Uani d S 1
C C5 0.41579(14) 0.2500 0.38425(9) 0.0419(4) Uani d S 1
H H5 0.3830 0.2500 0.3331 0.050 Uiso calc SR 1
C C6 0.51555(14) 0.2500 0.53673(9) 0.0410(4) Uani d S 1
H H6 0.5496 0.2500 0.5875 0.049 Uiso calc SR 1
C C7 0.33891(13) 0.2500 0.45124(9) 0.0378(4) Uani d S 1
C C8 0.38993(13) 0.2500 0.52944(8) 0.0373(4) Uani d S 1
C C9 0.21278(14) 0.2500 0.44446(10) 0.0470(4) Uani d S 1
H H9 0.1775 0.2500 0.3941 0.056 Uiso calc SR 1
C C10 0.31335(14) 0.2500 0.59644(9) 0.0424(4) Uani d S 1
H H10 0.3471 0.2500 0.6473 0.051 Uiso calc SR 1
C C11 0.14235(15) 0.2500 0.51082(10) 0.0487(4) Uani d S 1
H H11 0.0595 0.2500 0.5046 0.058 Uiso calc SR 1
C C12 0.19093(14) 0.2500 0.58935(10) 0.0434(4) Uani d S 1
C C13 0.10586(15) 0.2500 0.66087(11) 0.0555(5) Uani d S 1
C C14 0.1737(2) 0.2500 0.74021(12) 0.0857(8) Uani d S 1
C C15 0.02692(14) 0.0720(2) 0.65696(10) 0.0830(5) Uani d . 1
H H15A 0.0765 -0.0399 0.6589 0.124 Uiso calc R 1
H H15B -0.0181 0.0727 0.6080 0.124 Uiso calc R 1
H H15C -0.0273 0.0714 0.7016 0.124 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C3 . 179.47(18) n
N2 C2 C4 . 179.52(19) n
C5 C3 C4 . 119.97(14) n
C5 C3 C1 . 121.57(14) no
C4 C3 C1 . 118.46(14) no
C6 C4 C3 . 119.39(14) no
C6 C4 C2 . 120.52(14) no
C3 C4 C2 . 120.09(14) no
C3 C5 C7 . 121.20(14) no
C3 C5 H5 . 119.4 no
C7 C5 H5 . 119.4 no
C4 C6 C8 . 121.88(14) no
C4 C6 H6 . 119.1 no
C8 C6 H6 . 119.1 no
C5 C7 C9 . 122.82(14) no
C5 C7 C8 . 119.07(14) no
C9 C7 C8 . 118.11(14) no
C6 C8 C10 . 122.34(13) no
C6 C8 C7 . 118.48(13) no
C10 C8 C7 . 119.18(14) no
C11 C9 C7 . 120.68(14) no
C11 C9 H9 . 119.7 no
C7 C9 H9 . 119.7 no
C12 C10 C8 . 122.35(14) no
C12 C10 H10 . 118.8 no
C8 C10 H10 . 118.8 no
C9 C11 C12 . 122.30(15) no
C9 C11 H11 . 118.9 no
C12 C11 H11 . 118.9 no
C10 C12 C11 . 117.38(14) no
C10 C12 C13 . 123.46(15) no
C11 C12 C13 . 119.16(14) no
C12 C13 C14 . 111.89(14) n
C12 C13 C15 . 108.93(10) n
C14 C13 C15 . 108.82(11) n
C12 C13 C15 8_565 108.93(10) ?
C14 C13 C15 8_565 108.82(11) ?
C15 C13 C15 8_565 109.44(17) ?
C13 C14 H14B . 109.0 no
C13 C14 H14A . 113.3 no
H14B C14 H14A . 108.8 no
C13 C15 H15A . 109.5 no
C13 C15 H15B . 109.5 no
H15A C15 H15B . 109.5 no
C13 C15 H15C . 109.5 no
H15A C15 H15C . 109.5 no
H15B C15 H15C . 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 . 1.138(2) n
N2 C2 . 1.133(2) n
C1 C3 . 1.440(2) n
C2 C4 . 1.437(2) n
C3 C5 . 1.364(2) no
C3 C4 . 1.429(2) no
C4 C6 . 1.366(2) no
C5 C7 . 1.410(2) no
C5 H5 . 0.9300 no
C6 C8 . 1.406(2) no
C6 H6 . 0.9300 no
C7 C9 . 1.411(2) no
C7 C8 . 1.426(2) no
C8 C10 . 1.408(2) no
C9 C11 . 1.359(2) no
C9 H9 . 0.9300 no
C10 C12 . 1.370(2) no
C10 H10 . 0.9300 no
C11 C12 . 1.420(2) no
C11 H11 . 0.9300 no
C12 C13 . 1.526(2) n
C13 C14 . 1.527(3) n
C13 C15 . 1.5278(18) n
C13 C15 8_565 1.5278(18) n
C14 H14B . 0.9595 no
C14 H14A . 0.9637 no
C15 H15A . 0.9600 no
C15 H15B . 0.9600 no
C15 H15C . 0.9600 no
