#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/32/2223255.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_2223255
loop_
_publ_author_name
'Gondo, Chenaimwoyo A.'
'Lynch, Daniel E.'
'Hamilton, Darren G.'
_publ_section_title
;
 N,N'-Bis(1-ethynylcyclohexyl)pyromellitic diimide
;
_journal_coeditor_code           ZS2003
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2122
_journal_paper_doi               10.1107/S1600536809030979
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C26 H24 N2 O4'
_chemical_formula_moiety         'C26 H24 N2 O4'
_chemical_formula_sum            'C26 H24 N2 O4'
_chemical_formula_weight         428.47
_chemical_melting_point_gt       492
_chemical_melting_point_lt       493
_chemical_name_systematic
;
N,N'-Bis(1-ethynylcyclohexyl)pyromellitic diimide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.4950(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.1774(3)
_cell_length_b                   7.15190(10)
_cell_length_c                   11.8104(3)
_cell_measurement_reflns_used    2528
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1028.36(4)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics    'PLATON97 (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12939
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.30
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.800
_refine_ls_extinction_coef       0.38(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.288
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.288
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0910P)²+0.2895P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1582
_reflns_number_gt                1898
_reflns_number_total             2022
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2003.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223255
_cod_database_fobs_code          2223255
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.06501(9) 0.08401(16) 0.34794(11) 0.0222(4) Uani d . 1 . .
O O2 0.22629(9) 0.66713(15) 0.40367(11) 0.0202(4) Uani d . 1 . .
N N1 0.16857(10) 0.35785(17) 0.36123(11) 0.0156(4) Uani d . 1 . .
C C2 0.08812(12) 0.2440(2) 0.37881(13) 0.0158(4) Uani d . 1 . .
C C3 0.03482(12) 0.3636(2) 0.44392(13) 0.0151(4) Uani d . 1 . .
C C4 0.07781(12) 0.5432(2) 0.45479(13) 0.0152(4) Uani d . 1 . .
C C5 0.16567(12) 0.5404(2) 0.40426(13) 0.0158(4) Uani d . 1 . .
C C6 -0.04412(12) 0.3126(2) 0.48923(13) 0.0162(4) Uani d . 1 . .
H H1 -0.0726 0.1893 0.4825 0.020 Uiso calc R 1 . .
C C7 0.25590(11) 0.3002(2) 0.31631(13) 0.0150(4) Uani d . 1 . .
C C8 0.36865(12) 0.3129(2) 0.42496(14) 0.0169(4) Uani d . 1 . .
H H2 0.3812 0.4431 0.4557 0.021 Uiso calc R 1 . .
H H3 0.3680 0.2316 0.4925 0.021 Uiso calc R 1 . .
C C9 0.46204(12) 0.2530(2) 0.38642(15) 0.0208(4) Uani d . 1 . .
H H4 0.4676 0.3424 0.3251 0.026 Uiso calc R 1 . .
H H5 0.5323 0.2563 0.4586 0.026 Uiso calc R 1 . .
C C10 0.44355(13) 0.0570(2) 0.33209(16) 0.0250(4) Uani d . 1 . .
H H6 0.4485 -0.0345 0.3969 0.031 Uiso calc R 1 . .
H H7 0.5020 0.0272 0.3017 0.031 Uiso calc R 1 . .
C C11 0.33156(13) 0.0392(2) 0.22690(15) 0.0210(4) Uani d . 1 . .
H H8 0.3201 -0.0920 0.1979 0.026 Uiso calc R 1 . .
H H9 0.3298 0.1191 0.1578 0.026 Uiso calc R 1 . .
C C12 0.23911(12) 0.0975(2) 0.26781(13) 0.0169(4) Uani d . 1 . .
H H10 0.2376 0.0120 0.3331 0.021 Uiso calc R 1 . .
H H11 0.1677 0.0875 0.1977 0.021 Uiso calc R 1 . .
C C13 0.25281(12) 0.4268(2) 0.21565(14) 0.0178(4) Uani d . 1 . .
C C14 0.25817(13) 0.5152(2) 0.13290(15) 0.0211(4) Uani d . 1 . .
H H12 0.2625 0.5858 0.0668 0.026 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'
O O 0.0106 0.0060 '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
C5 N1 C2 . . 110.85(12) ?
C5 N1 C7 . . 120.94(12) ?
C2 N1 C7 . . 127.92(12) ?
O1 C2 N1 . . 128.31(14) ?
O1 C2 C3 . . 125.88(13) ?
N1 C2 C3 . . 105.81(12) ?
C6 C3 C4 . . 123.13(14) ?
C6 C3 C2 . . 128.11(14) ?
C4 C3 C2 . . 108.76(13) ?
C3 C4 C6 . 3_566 122.54(14) ?
C3 C4 C5 . . 107.58(13) ?
C6 C4 C5 3_566 . 129.77(14) ?
O2 C5 N1 . . 125.73(14) ?
O2 C5 C4 . . 127.39(14) ?
N1 C5 C4 . . 106.83(12) ?
C3 C6 C4 . 3_566 114.32(14) ?
C3 C6 H1 . . 122.8 ?
C4 C6 H1 3_566 . 122.8 ?
C13 C7 N1 . . 109.08(12) ?
C13 C7 C12 . . 108.67(12) ?
N1 C7 C12 . . 111.69(12) ?
C13 C7 C8 . . 110.59(12) ?
N1 C7 C8 . . 108.28(11) ?
C12 C7 C8 . . 108.54(12) ?
C9 C8 C7 . . 111.30(12) ?
C9 C8 H2 . . 109.4 ?
C7 C8 H2 . . 109.4 ?
C9 C8 H3 . . 109.4 ?
C7 C8 H3 . . 109.4 ?
H2 C8 H3 . . 108.0 ?
C10 C9 C8 . . 111.50(13) ?
C10 C9 H4 . . 109.3 ?
C8 C9 H4 . . 109.3 ?
C10 C9 H5 . . 109.3 ?
C8 C9 H5 . . 109.3 ?
H4 C9 H5 . . 108.0 ?
C9 C10 C11 . . 111.64(13) ?
C9 C10 H6 . . 109.3 ?
C11 C10 H6 . . 109.3 ?
C9 C10 H7 . . 109.3 ?
C11 C10 H7 . . 109.3 ?
H6 C10 H7 . . 108.0 ?
C10 C11 C12 . . 111.00(12) ?
C10 C11 H8 . . 109.4 ?
C12 C11 H8 . . 109.4 ?
C10 C11 H9 . . 109.4 ?
C12 C11 H9 . . 109.4 ?
H8 C11 H9 . . 108.0 ?
C11 C12 C7 . . 110.79(12) ?
C11 C12 H10 . . 109.5 ?
C7 C12 H10 . . 109.5 ?
C11 C12 H11 . . 109.5 ?
C7 C12 H11 . . 109.5 ?
H10 C12 H11 . . 108.1 ?
C14 C13 C7 . . 172.85(16) ?
C13 C14 H12 . . 180.0 ?
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
O1 C2 . 1.2042(19) ?
O2 C5 . 1.2100(18) ?
N1 C5 . 1.4066(19) ?
N1 C2 . 1.4136(19) ?
N1 C7 . 1.4976(18) ?
C2 C3 . 1.493(2) ?
C3 C6 . 1.388(2) ?
C3 C4 . 1.389(2) ?
C4 C6 3_566 1.387(2) ?
C4 C5 . 1.492(2) ?
C6 C4 3_566 1.387(2) ?
C6 H1 . 0.95 ?
C7 C13 . 1.482(2) ?
C7 C12 . 1.543(2) ?
C7 C8 . 1.550(2) ?
C8 C9 . 1.528(2) ?
C8 H2 . 0.99 ?
C8 H3 . 0.99 ?
C9 C10 . 1.522(2) ?
C9 H4 . 0.99 ?
C9 H5 . 0.99 ?
C10 C11 . 1.528(2) ?
C10 H6 . 0.99 ?
C10 H7 . 0.99 ?
C11 C12 . 1.530(2) ?
C11 H8 . 0.99 ?
C11 H9 . 0.99 ?
C12 H10 . 0.99 ?
C12 H11 . 0.99 ?
C13 C14 . 1.188(2) ?
C14 H12 . 0.95 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C14 H12 O2 4_575 0.95 2.52 3.4349(19) 161.4 yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C2 O1 . . . . 176.47(15) ?
C7 N1 C2 O1 . . . . -9.7(2) ?
C5 N1 C2 C3 . . . . -3.03(16) ?
C7 N1 C2 C3 . . . . 170.78(13) ?
O1 C2 C3 C6 . . . . 5.3(3) ?
N1 C2 C3 C6 . . . . -175.23(14) ?
O1 C2 C3 C4 . . . . -175.27(14) ?
N1 C2 C3 C4 . . . . 4.25(16) ?
C6 C3 C4 C6 . . . 3_566 -0.8(3) ?
C2 C3 C4 C6 . . . 3_566 179.65(13) ?
C6 C3 C4 C5 . . . . 175.74(13) ?
C2 C3 C4 C5 . . . . -3.77(16) ?
C2 N1 C5 O2 . . . . 178.38(14) ?
C7 N1 C5 O2 . . . . 4.1(2) ?
C2 N1 C5 C4 . . . . 0.82(16) ?
C7 N1 C5 C4 . . . . -173.49(12) ?
C3 C4 C5 O2 . . . . -175.58(15) ?
C6 C4 C5 O2 3_566 . . . 0.7(3) ?
C3 C4 C5 N1 . . . . 1.92(16) ?
C6 C4 C5 N1 3_566 . . . 178.17(14) ?
C4 C3 C6 C4 . . . 3_566 0.8(2) ?
C2 C3 C6 C4 . . . 3_566 -179.81(14) ?
C5 N1 C7 C13 . . . . -57.01(17) ?
C2 N1 C7 C13 . . . . 129.74(15) ?
C5 N1 C7 C12 . . . . -177.14(12) ?
C2 N1 C7 C12 . . . . 9.6(2) ?
C5 N1 C7 C8 . . . . 63.40(17) ?
C2 N1 C7 C8 . . . . -109.86(16) ?
C13 C7 C8 C9 . . . . -61.41(16) ?
N1 C7 C8 C9 . . . . 179.13(12) ?
C12 C7 C8 C9 . . . . 57.70(16) ?
C7 C8 C9 C10 . . . . -56.05(17) ?
C8 C9 C10 C11 . . . . 54.10(18) ?
C9 C10 C11 C12 . . . . -54.98(18) ?
C10 C11 C12 C7 . . . . 57.87(17) ?
C13 C7 C12 C11 . . . . 61.74(15) ?
N1 C7 C12 C11 . . . . -177.88(11) ?
C8 C7 C12 C11 . . . . -58.57(15) ?
