#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:59:53 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178415 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/36/4023667.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023667
loop_
_publ_author_name
'Gui-Hong Liao'
'Lin Luo'
'Hong-Xia Xu'
'Xiao-Ling Wu'
'Lei Lei'
'Chen-Ho Tung'
'Li-Zhu Wu'
_publ_section_title
;
 Formation of Cubane-like Photodimers from 2-Naphthalenecarbonitrile
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7345
_journal_page_last               7348
_journal_paper_doi               10.1021/jo800927t
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C22 H14 N2'
_chemical_formula_weight         306.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 105.96(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.397(3)
_cell_length_b                   8.5763(17)
_cell_length_c                   15.405(3)
_cell_measurement_reflns_used    8637
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.47
_cell_volume                     1574.7(5)
_computing_cell_refinement       Rapid-AUTO
_computing_data_collection       'Rapid-AUTO (Rigaku,2000)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC,2000)'
_computing_molecular_graphics    'Siemens SHELXTL V4.2,(Sheldrick,1990)'
_computing_publication_material  SHELXL-97,(Sheldrick,1997)
_computing_structure_refinement  SHELXL-97,(Sheldrick,1997)
_computing_structure_solution    SHELXS-97,(Sheldrick,1997)
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8637
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
                                  HIGASHI, T. (1995). Abscor-Empirical
                                  Absorption Correction based on Fourier
                                  Series Approximation.
                                  Rigaku Corporation,Tokyo,Japan.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.069(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   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0405
_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)+(0.0550P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                1829
_reflns_number_total             2757
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800927t_si_001_1.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023667
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.55645(16) 0.7023(2) 0.60870(12) 0.0701(5) Uani 1 1 d . . .
N2 N 0.64923(15) 0.0437(2) 0.52298(11) 0.0636(5) Uani 1 1 d . . .
C1 C 0.55685(14) 0.4294(2) 0.68053(10) 0.0394(4) Uani 1 1 d . . .
C2 C 0.47738(14) 0.3049(2) 0.62389(10) 0.0397(4) Uani 1 1 d . . .
H2 H 0.4405 0.3288 0.5604 0.048 Uiso 1 1 calc R . .
C3 C 0.57503(13) 0.1839(2) 0.64484(10) 0.0390(4) Uani 1 1 d . . .
C4 C 0.65493(14) 0.3089(2) 0.70084(11) 0.0418(5) Uani 1 1 d . . .
H4 H 0.7230 0.3354 0.6834 0.050 Uiso 1 1 calc R . .
C5 C 0.66030(14) 0.3115(2) 0.80275(11) 0.0419(4) Uani 1 1 d . . .
H5 H 0.7305 0.3596 0.8378 0.050 Uiso 1 1 calc R . .
C6 C 0.56154(14) 0.4346(2) 0.78299(10) 0.0391(4) Uani 1 1 d . . .
H6 H 0.5894 0.5361 0.8089 0.047 Uiso 1 1 calc R . .
C7 C 0.41192(13) 0.2061(2) 0.67634(10) 0.0371(4) Uani 1 1 d . . .
H7 H 0.3444 0.1620 0.6346 0.044 Uiso 1 1 calc R . .
C8 C 0.51025(14) 0.0815(2) 0.69757(10) 0.0380(4) Uani 1 1 d . . .
H8 H 0.4852 -0.0161 0.6652 0.046 Uiso 1 1 calc R . .
C9 C 0.56829(14) 0.0500(2) 0.79510(11) 0.0395(4) Uani 1 1 d . . .
C10 C 0.54656(16) -0.0858(2) 0.83704(13) 0.0547(5) Uani 1 1 d . . .
H10 H 0.4994 -0.1614 0.8034 0.066 Uiso 1 1 calc R . .
C11 C 0.5946(2) -0.1086(3) 0.92823(14) 0.0740(7) Uani 1 1 d . . .
H11 H 0.5788 -0.1985 0.9562 0.089 Uiso 1 1 calc R . .
C12 C 0.6663(2) 0.0024(3) 0.97777(14) 0.0739(7) Uani 1 1 d . . .
H12 H 0.6989 -0.0133 1.0391 0.089 Uiso 1 1 calc R . .
C13 C 0.68968(16) 0.1354(3) 0.93717(12) 0.0576(6) Uani 1 1 d . . .
H13 H 0.7387 0.2089 0.9711 0.069 Uiso 1 1 calc R . .
C14 C 0.64058(14) 0.1619(2) 0.84522(11) 0.0408(4) Uani 1 1 d . . .
C15 C 0.45540(13) 0.39399(19) 0.80563(10) 0.0363(4) Uani 1 1 d . . .
C16 C 0.42831(15) 0.4637(2) 0.87878(10) 0.0448(5) Uani 1 1 d . . .
H16 H 0.4760 0.5386 0.9126 0.054 Uiso 1 1 calc R . .
C17 C 0.33207(16) 0.4234(2) 0.90177(11) 0.0499(5) Uani 1 1 d . . .
H17 H 0.3159 0.4696 0.9514 0.060 Uiso 1 1 calc R . .
C18 C 0.26008(16) 0.3148(2) 0.85112(12) 0.0519(5) Uani 1 1 d . . .
H18 H 0.1948 0.2880 0.8662 0.062 Uiso 1 1 calc R . .
C19 C 0.28482(15) 0.2450(2) 0.77733(11) 0.0473(5) Uani 1 1 d . . .
H19 H 0.2356 0.1720 0.7431 0.057 Uiso 1 1 calc R . .
C20 C 0.38269(13) 0.2835(2) 0.75411(10) 0.0375(4) Uani 1 1 d . . .
C21 C 0.55766(16) 0.5802(2) 0.63914(12) 0.0480(5) Uani 1 1 d . . .
C22 C 0.61541(15) 0.1059(2) 0.57587(11) 0.0443(5) Uani 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 C1 C2 116.70(14) . . ?
C21 C1 C4 125.61(15) . . ?
C2 C1 C4 89.79(13) . . ?
C21 C1 C6 114.68(15) . . ?
C2 C1 C6 115.44(14) . . ?
C4 C1 C6 90.34(12) . . ?
C7 C2 C1 115.30(13) . . ?
C7 C2 C3 90.91(12) . . ?
C1 C2 C3 90.29(13) . . ?
C7 C2 H2 117.9 . . ?
C1 C2 H2 117.9 . . ?
C3 C2 H2 117.9 . . ?
C22 C3 C4 115.37(14) . . ?
C22 C3 C2 123.91(14) . . ?
C4 C3 C2 89.73(13) . . ?
C22 C3 C8 116.82(15) . . ?
C4 C3 C8 116.16(13) . . ?
C2 C3 C8 90.05(12) . . ?
C3 C4 C5 114.54(14) . . ?
C3 C4 C1 90.18(13) . . ?
C5 C4 C1 90.44(12) . . ?
C3 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
C1 C4 H4 118.3 . . ?
C14 C5 C4 117.69(15) . . ?
C14 C5 C6 116.58(14) . . ?
C4 C5 C6 89.95(12) . . ?
C14 C5 H5 110.4 . . ?
C4 C5 H5 110.4 . . ?
C6 C5 H5 110.4 . . ?
C15 C6 C1 116.02(14) . . ?
C15 C6 C5 119.01(14) . . ?
C1 C6 C5 89.27(12) . . ?
C15 C6 H6 110.3 . . ?
C1 C6 H6 110.3 . . ?
C5 C6 H6 110.3 . . ?
C20 C7 C2 116.87(14) . . ?
C20 C7 C8 118.34(13) . . ?
C2 C7 C8 89.59(12) . . ?
C20 C7 H7 110.2 . . ?
C2 C7 H7 110.2 . . ?
C8 C7 H7 110.2 . . ?
C9 C8 C3 116.67(14) . . ?
C9 C8 C7 117.23(13) . . ?
C3 C8 C7 89.45(12) . . ?
C9 C8 H8 110.6 . . ?
C3 C8 H8 110.6 . . ?
C7 C8 H8 110.6 . . ?
C14 C9 C10 119.72(16) . . ?
C14 C9 C8 119.25(15) . . ?
C10 C9 C8 120.95(16) . . ?
C11 C10 C9 120.39(19) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.44(19) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.66(19) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C9 C14 C13 118.97(17) . . ?
C9 C14 C5 120.54(14) . . ?
C13 C14 C5 120.41(17) . . ?
C20 C15 C16 119.26(16) . . ?
C20 C15 C6 119.93(14) . . ?
C16 C15 C6 120.81(16) . . ?
C17 C16 C15 121.18(18) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C18 C17 C16 119.76(17) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.04(18) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 120.68(18) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 119.07(15) . . ?
C15 C20 C7 119.68(14) . . ?
C19 C20 C7 121.24(16) . . ?
N1 C21 C1 177.3(2) . . ?
N2 C22 C3 178.54(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C21 1.146(2) . ?
N2 C22 1.145(2) . ?
C1 C21 1.443(2) . ?
C1 C2 1.549(2) . ?
C1 C4 1.560(2) . ?
C1 C6 1.564(2) . ?
C2 C7 1.546(2) . ?
C2 C3 1.560(2) . ?
C2 H2 0.9800 . ?
C3 C22 1.456(2) . ?
C3 C4 1.551(2) . ?
C3 C8 1.560(2) . ?
C4 C5 1.553(2) . ?
C4 H4 0.9800 . ?
C5 C14 1.491(2) . ?
C5 C6 1.582(2) . ?
C5 H5 0.9800 . ?
C6 C15 1.492(2) . ?
C6 H6 0.9800 . ?
C7 C20 1.499(2) . ?
C7 C8 1.586(2) . ?
C7 H7 0.9800 . ?
C8 C9 1.501(2) . ?
C8 H8 0.9800 . ?
C9 C14 1.393(2) . ?
C9 C10 1.393(2) . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.398(2) . ?
C13 H13 0.9300 . ?
C15 C20 1.395(2) . ?
C15 C16 1.396(2) . ?
C16 C17 1.378(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.375(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.391(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.396(2) . ?
C19 H19 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 C1 C2 C7 -137.83(15) . . . . ?
C4 C1 C2 C7 91.63(15) . . . . ?
C6 C1 C2 C7 1.4(2) . . . . ?
C21 C1 C2 C3 131.03(15) . . . . ?
C4 C1 C2 C3 0.49(12) . . . . ?
C6 C1 C2 C3 -89.78(16) . . . . ?
C7 C2 C3 C22 123.33(17) . . . . ?
C1 C2 C3 C22 -121.36(17) . . . . ?
C7 C2 C3 C4 -115.80(12) . . . . ?
C1 C2 C3 C4 -0.49(12) . . . . ?
C7 C2 C3 C8 0.36(12) . . . . ?
C1 C2 C3 C8 115.67(12) . . . . ?
C22 C3 C4 C5 -140.98(15) . . . . ?
C2 C3 C4 C5 91.05(15) . . . . ?
C8 C3 C4 C5 1.1(2) . . . . ?
C22 C3 C4 C1 128.46(14) . . . . ?
C2 C3 C4 C1 0.49(12) . . . . ?
C8 C3 C4 C1 -89.43(15) . . . . ?
C21 C1 C4 C3 -123.86(17) . . . . ?
C2 C1 C4 C3 -0.49(12) . . . . ?
C6 C1 C4 C3 114.95(13) . . . . ?
C21 C1 C4 C5 121.59(17) . . . . ?
C2 C1 C4 C5 -115.04(13) . . . . ?
C6 C1 C4 C5 0.40(13) . . . . ?
C3 C4 C5 C14 29.5(2) . . . . ?
C1 C4 C5 C14 119.92(15) . . . . ?
C3 C4 C5 C6 -90.80(15) . . . . ?
C1 C4 C5 C6 -0.40(13) . . . . ?
C21 C1 C6 C15 107.32(18) . . . . ?
C2 C1 C6 C15 -32.7(2) . . . . ?
C4 C1 C6 C15 -122.63(15) . . . . ?
C21 C1 C6 C5 -130.45(15) . . . . ?
C2 C1 C6 C5 89.53(15) . . . . ?
C4 C1 C6 C5 -0.40(13) . . . . ?
C14 C5 C6 C15 -1.2(2) . . . . ?
C4 C5 C6 C15 120.04(15) . . . . ?
C14 C5 C6 C1 -120.88(15) . . . . ?
C4 C5 C6 C1 0.40(13) . . . . ?
C1 C2 C7 C20 30.8(2) . . . . ?
C3 C2 C7 C20 121.56(14) . . . . ?
C1 C2 C7 C8 -91.10(15) . . . . ?
C3 C2 C7 C8 -0.35(12) . . . . ?
C22 C3 C8 C9 110.45(17) . . . . ?
C4 C3 C8 C9 -31.1(2) . . . . ?
C2 C3 C8 C9 -120.83(15) . . . . ?
C22 C3 C8 C7 -129.07(14) . . . . ?
C4 C3 C8 C7 89.38(15) . . . . ?
C2 C3 C8 C7 -0.35(12) . . . . ?
C20 C7 C8 C9 -0.3(2) . . . . ?
C2 C7 C8 C9 120.35(15) . . . . ?
C20 C7 C8 C3 -120.29(15) . . . . ?
C2 C7 C8 C3 0.35(12) . . . . ?
C3 C8 C9 C14 31.7(2) . . . . ?
C7 C8 C9 C14 -72.6(2) . . . . ?
C3 C8 C9 C10 -151.51(16) . . . . ?
C7 C8 C9 C10 104.2(2) . . . . ?
C14 C9 C10 C11 1.2(3) . . . . ?
C8 C9 C10 C11 -175.59(18) . . . . ?
C9 C10 C11 C12 -1.2(3) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C10 C9 C14 C13 -0.2(3) . . . . ?
C8 C9 C14 C13 176.60(16) . . . . ?
C10 C9 C14 C5 -176.81(16) . . . . ?
C8 C9 C14 C5 0.0(2) . . . . ?
C12 C13 C14 C9 -0.7(3) . . . . ?
C12 C13 C14 C5 175.90(19) . . . . ?
C4 C5 C14 C9 -31.8(2) . . . . ?
C6 C5 C14 C9 73.4(2) . . . . ?
C4 C5 C14 C13 151.71(17) . . . . ?
C6 C5 C14 C13 -103.13(19) . . . . ?
C1 C6 C15 C20 33.3(2) . . . . ?
C5 C6 C15 C20 -71.47(19) . . . . ?
C1 C6 C15 C16 -147.64(15) . . . . ?
C5 C6 C15 C16 107.62(18) . . . . ?
C20 C15 C16 C17 1.0(2) . . . . ?
C6 C15 C16 C17 -178.06(16) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C16 C15 C20 C19 -0.2(2) . . . . ?
C6 C15 C20 C19 178.86(15) . . . . ?
C16 C15 C20 C7 -179.00(15) . . . . ?
C6 C15 C20 C7 0.1(2) . . . . ?
C18 C19 C20 C15 -0.4(3) . . . . ?
C18 C19 C20 C7 178.32(16) . . . . ?
C2 C7 C20 C15 -33.2(2) . . . . ?
C8 C7 C20 C15 72.1(2) . . . . ?
C2 C7 C20 C19 148.08(16) . . . . ?
C8 C7 C20 C19 -106.60(19) . . . . ?
C2 C1 C21 N1 112(5) . . . . ?
C4 C1 C21 N1 -137(5) . . . . ?
C6 C1 C21 N1 -27(5) . . . . ?
C4 C3 C22 N2 55(8) . . . . ?
C2 C3 C22 N2 163(8) . . . . ?
C8 C3 C22 N2 -87(8) . . . . ?
