#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/94/2219436.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_2219436
loop_
_publ_author_name
'Shukla, Deepak'
'Rajeswaran, Manju'
_publ_section_title
;
 N,N'-Dicyclohexylnaphthalene-1,8;4:5-dicarboximide
;
_journal_coeditor_code           SJ2528
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1735
_journal_paper_doi               10.1107/S1600536808025221
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C26 H26 N2 O4'
_chemical_formula_moiety         'C26 H26 N2 O4'
_chemical_formula_sum            'C26 H26 N2 O4'
_chemical_formula_weight         430.49
_chemical_name_common            NDICHex
_chemical_name_systematic
;
N,N'-dicyclohexylnaphthalene-1,8;4:5-dicarboximide
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00000
_cell_angle_beta                 102.4790(18)
_cell_angle_gamma                90.00000
_cell_formula_units_Z            2
_cell_length_a                   8.5410(2)
_cell_length_b                   6.6780(2)
_cell_length_c                   18.4270(9)
_cell_measurement_reflns_used    21067
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1026.19(6)
_computing_cell_refinement
;
SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
COLLECT (Nonius, 2000)
;
_computing_data_reduction
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics
;
SHELXTL  (Sheldrick, 2008)
;
_computing_publication_material  'publCIF (Westrip, 2007)'
_computing_structure_refinement
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_solution
;
SIR97 (Altomare et al., 1999)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0870
_diffrn_reflns_av_sigmaI/netI    0.0659
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3354
_diffrn_reflns_theta_full        27.35
_diffrn_reflns_theta_max         27.35
_diffrn_reflns_theta_min         4.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.291
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1227
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0665
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0638P)²+1.0546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.1821
_reflns_number_gt                787
_reflns_number_total             1227
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2528.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               2219436
_cod_database_fobs_code          2219436
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
O O1 0.2160(3) 0.0000 0.28476(12) 0.0594(8) Uani d S 1
O O2 0.7630(3) 0.0000 0.33332(13) 0.0647(8) Uani d S 1
N N1 0.4894(3) 0.0000 0.30625(13) 0.0431(7) Uani d S 1
C C1 0.6391(4) 0.0000 0.35566(18) 0.0457(8) Uani d S 1
C C2 0.6418(3) 0.0000 0.43622(17) 0.0422(8) Uani d S 1
C C3 0.7854(4) 0.0000 0.48703(18) 0.0510(9) Uani d S 1
H H3 0.8806 0.0000 0.4703 0.061 Uiso calc SR 1
C C4 0.4979(3) 0.0000 0.46157(16) 0.0384(7) Uani d S 1
C C5 0.2086(4) 0.0000 0.43639(18) 0.0494(9) Uani d S 1
H H5 0.1100 0.0000 0.4030 0.059 Uiso calc SR 1
C C6 0.3486(3) 0.0000 0.41020(17) 0.0410(7) Uani d S 1
C C7 0.3427(4) 0.0000 0.32968(18) 0.0446(8) Uani d S 1
C C8 0.4868(4) 0.0000 0.22507(16) 0.0460(8) Uani d S 1
H H8 0.5991 0.0000 0.2207 0.055 Uiso calc SR 1
C C9 0.4125(3) 0.1896(4) 0.18665(13) 0.0591(7) Uani d . 1
H H9A 0.4684 0.3060 0.2110 0.071 Uiso calc R 1
H H9B 0.3010 0.1986 0.1901 0.071 Uiso calc R 1
C C10 0.4238(3) 0.1862(5) 0.10529(14) 0.0708(9) Uani d . 1
H H10A 0.3699 0.3031 0.0803 0.085 Uiso calc R 1
H H10B 0.5356 0.1926 0.1022 0.085 Uiso calc R 1
C C11 0.3488(5) 0.0000 0.0665(2) 0.0664(11) Uani d S 1
H H11A 0.3624 0.0000 0.0156 0.080 Uiso calc SR 1
H H11B 0.2348 0.0000 0.0654 0.080 Uiso calc SR 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'
O O 0.0106 0.0060 '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 N1 C7 . . 123.2(3)
C1 N1 C8 . . 117.8(3)
C7 N1 C8 . . 119.0(2)
O2 C1 N1 . . 121.3(3)
O2 C1 C2 . . 120.9(3)
N1 C1 C2 . . 117.8(3)
C3 C2 C4 . . 119.3(3)
C3 C2 C1 . . 120.1(3)
C4 C2 C1 . . 120.5(3)
C2 C3 C5 . 5_656 121.3(3)
C2 C3 H3 . . 119.3
C5 C3 H3 5_656 . 119.3
C2 C4 C4 . 5_656 120.0(3)
C2 C4 C6 . . 120.3(3)
C4 C4 C6 5_656 . 119.7(3)
C6 C5 C3 . 5_656 120.4(3)
C6 C5 H5 . . 119.8
C3 C5 H5 5_656 . 119.8
C5 C6 C4 . . 119.3(3)
C5 C6 C7 . . 120.5(3)
C4 C6 C7 . . 120.2(3)
O1 C7 N1 . . 120.8(3)
O1 C7 C6 . . 121.2(3)
N1 C7 C6 . . 118.0(2)
N1 C8 C9 . 6 112.42(17)
N1 C8 C9 . . 112.42(17)
C9 C8 C9 6 . 112.7(3)
N1 C8 H8 . . 106.2
C9 C8 H8 6 . 106.2
C9 C8 H8 . . 106.2
C8 C9 C10 . . 109.7(2)
C8 C9 H9A . . 109.7
C10 C9 H9A . . 109.7
C8 C9 H9B . . 109.7
C10 C9 H9B . . 109.7
H9A C9 H9B . . 108.2
C11 C10 C9 . . 111.6(3)
C11 C10 H10A . . 109.3
C9 C10 H10A . . 109.3
C11 C10 H10B . . 109.3
C9 C10 H10B . . 109.3
H10A C10 H10B . . 108.0
C10 C11 C10 . 6 111.3(3)
C10 C11 H11A . . 109.4
C10 C11 H11A 6 . 109.4
C10 C11 H11B . . 109.4
C10 C11 H11B 6 . 109.4
H11A C11 H11B . . 108.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C7 . 1.212(3)
O2 C1 . 1.216(4)
N1 C1 . 1.401(4)
N1 C7 . 1.411(4)
N1 C8 . 1.491(4)
C1 C2 . 1.480(4)
C2 C3 . 1.373(4)
C2 C4 . 1.406(4)
C3 C5 5_656 1.401(4)
C3 H3 . 0.9300
C4 C4 5_656 1.409(6)
C4 C6 . 1.415(4)
C5 C6 . 1.382(4)
C5 C3 5_656 1.401(4)
C5 H5 . 0.9300
C6 C7 . 1.474(4)
C8 C9 6 1.521(3)
C8 C9 . 1.521(3)
C8 H8 . 0.9800
C9 C10 . 1.523(3)
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 C11 . 1.506(4)
C10 H10A . 0.9700
C10 H10B . 0.9700
C11 C10 6 1.506(4)
C11 H11A . 0.9700
C11 H11B . 0.9700
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_1
_geom_torsion_site_symmetry_4
_geom_torsion
C7 N1 C1 O2 . . 180.0
C8 N1 C1 O2 . . 0.0
C7 N1 C1 C2 . . 0.0
C8 N1 C1 C2 . . 180.0
O2 C1 C2 C3 . . 0.0
N1 C1 C2 C3 . . 180.0
O2 C1 C2 C4 . . 180.0
N1 C1 C2 C4 . . 0.0
C4 C2 C3 C5 . 5_656 0.0000(10)
C1 C2 C3 C5 . 5_656 180.0
C3 C2 C4 C4 . 5_656 0.0
C1 C2 C4 C4 . 5_656 180.0
C3 C2 C4 C6 . . 180.0
C1 C2 C4 C6 . . 0.0
C3 C5 C6 C4 5_656 . 0.0000(10)
C3 C5 C6 C7 5_656 . 180.0
C2 C4 C6 C5 . . 180.0
C4 C4 C6 C5 5_656 . 0.0000(10)
C2 C4 C6 C7 . . 0.0
C4 C4 C6 C7 5_656 . 180.0
C1 N1 C7 O1 . . 180.0
C8 N1 C7 O1 . . 0.0
C1 N1 C7 C6 . . 0.0
C8 N1 C7 C6 . . 180.0
C5 C6 C7 O1 . . 0.0
C4 C6 C7 O1 . . 180.0
C5 C6 C7 N1 . . 180.0
C4 C6 C7 N1 . . 0.0
C1 N1 C8 C9 . 6 115.76(19)
C7 N1 C8 C9 . 6 -64.24(19)
C1 N1 C8 C9 . . -115.76(19)
C7 N1 C8 C9 . . 64.24(19)
N1 C8 C9 C10 . . 176.2(2)
C9 C8 C9 C10 6 . -55.5(4)
C8 C9 C10 C11 . . 55.2(3)
C9 C10 C11 C10 . 6 -56.5(4)
