#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/99/2229949.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_2229949
loop_
_publ_author_name
'Liu, Yanju'
'Liu, Kai'
'Cao, Zhiqiang'
'Niu, Meiju'
_publ_section_title
;
 1,1'-[(1E,11E)-5,8-Dioxa-2,11-diazoniadodeca-1,11-diene-1,12-diyl]dinaphthalen-2-olate
;
_journal_coeditor_code           CV5066
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1074
_journal_paper_doi               10.1107/S1600536811012219
_journal_volume                  67
_journal_year                    2011
_chemical_formula_moiety         'C28 H28 N2 O4'
_chemical_formula_sum            'C28 H28 N2 O4'
_chemical_formula_weight         456.52
_chemical_name_systematic
;
1,1'-[(1E,11E)-5,8-Dioxa-2,11-diazoniadodeca-1,11-diene-\
1,12-diyl]dinaphthalen-2-olate
;
_space_group_IT_number           54
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2a 2ac'
_symmetry_space_group_name_H-M   'P c c 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                   44.704(4)
_cell_length_b                   6.3576(6)
_cell_length_c                   8.2074(9)
_cell_measurement_reflns_used    1398
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.6135
_cell_measurement_theta_min      2.734
_cell_volume                     2332.6(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0807
_diffrn_reflns_av_sigmaI/netI    0.0665
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9099
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_correction_T_min  0.9577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.192
_refine_ls_extinction_coef       0.0055(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0677
_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)+(0.0880P)²+3.8548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1864
_refine_ls_wR_factor_ref         0.2235
_reflns_number_gt                1162
_reflns_number_total             2060
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cv5066.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P c c a '
_cod_database_code               2229949
_cod_database_fobs_code          2229949
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x, -y, z-1/2'
'-x-1/2, y, 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
N N1 0.16369(7) 0.4462(5) 0.0795(4) 0.0479(10) Uani d . 1 . .
H H1A 0.1720 0.5537 0.1239 0.058 Uiso calc R 1 . .
C C2 0.11853(8) 0.6454(6) 0.0728(5) 0.0370(9) Uani d . 1 . .
O O1 0.15974(7) 0.8123(5) 0.2021(4) 0.0628(10) Uani d . 1 . .
O O2 0.22075(6) 0.4082(5) 0.2116(4) 0.0541(9) Uani d . 1 . .
C C11 0.08741(8) 0.6581(6) 0.0253(5) 0.0388(10) Uani d . 1 . .
C C1 0.13580(8) 0.4646(6) 0.0400(5) 0.0402(10) Uani d . 1 . .
H H1 0.1266 0.3525 -0.0129 0.048 Uiso calc R 1 . .
C C6 0.07056(9) 0.8373(6) 0.0703(5) 0.0464(11) Uani d . 1 . .
C C3 0.13216(10) 0.8124(6) 0.1618(5) 0.0463(11) Uani d . 1 . .
C C10 0.07267(8) 0.5045(7) -0.0672(5) 0.0469(11) Uani d . 1 . .
H H10 0.0832 0.3861 -0.1007 0.056 Uiso calc R 1 . .
C C12 0.18209(9) 0.2620(7) 0.0560(6) 0.0505(12) Uani d . 1 . .
H H12A 0.1941 0.2793 -0.0415 0.061 Uiso calc R 1 . .
H H12B 0.1694 0.1397 0.0410 0.061 Uiso calc R 1 . .
C C4 0.11373(10) 0.9880(7) 0.2060(6) 0.0557(12) Uani d . 1 . .
H H4 0.1220 1.0978 0.2657 0.067 Uiso calc R 1 . .
C C5 0.08502(10) 0.9976(7) 0.1636(5) 0.0550(12) Uani d . 1 . .
H H5 0.0739 1.1138 0.1962 0.066 Uiso calc R 1 . .
C C8 0.02674(10) 0.6990(9) -0.0632(6) 0.0650(14) Uani d . 1 . .
H H8 0.0067 0.7120 -0.0922 0.078 Uiso calc R 1 . .
C C7 0.04054(10) 0.8504(8) 0.0252(6) 0.0572(13) Uani d . 1 . .
H H7 0.0296 0.9677 0.0571 0.069 Uiso calc R 1 . .
C C9 0.04327(9) 0.5238(8) -0.1096(6) 0.0553(12) Uani d . 1 . .
H H9 0.0342 0.4182 -0.1703 0.066 Uiso calc R 1 . .
C C13 0.20210(9) 0.2282(7) 0.1994(6) 0.0566(13) Uani d . 1 . .
H H13A 0.1903 0.2115 0.2979 0.068 Uiso calc R 1 . .
H H13B 0.2141 0.1027 0.1840 0.068 Uiso calc R 1 . .
C C14 0.24105(8) 0.4015(7) 0.3430(5) 0.0507(12) Uani d . 1 . .
H H14A 0.2542 0.2808 0.3319 0.061 Uiso calc R 1 . .
H H14B 0.2302 0.3884 0.4449 0.061 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'
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
_geom_angle_publ_flag
C1 N1 C12 . . 126.1(4) ?
C1 N1 H1A . . 117.0 ?
C12 N1 H1A . . 117.0 ?
C1 C2 C3 . . 118.1(3) ?
C1 C2 C11 . . 121.4(3) ?
C3 C2 C11 . . 120.5(4) ?
C14 O2 C13 . . 114.1(3) ?
C10 C11 C6 . . 116.9(4) ?
C10 C11 C2 . . 124.0(4) ?
C6 C11 C2 . . 119.1(4) ?
N1 C1 C2 . . 123.6(4) ?
N1 C1 H1 . . 118.2 ?
C2 C1 H1 . . 118.2 ?
C7 C6 C11 . . 119.4(4) ?
C7 C6 C5 . . 122.3(4) ?
C11 C6 C5 . . 118.2(4) ?
O1 C3 C2 . . 123.1(4) ?
O1 C3 C4 . . 119.3(4) ?
C2 C3 C4 . . 117.6(4) ?
C9 C10 C11 . . 121.9(4) ?
C9 C10 H10 . . 119.1 ?
C11 C10 H10 . . 119.1 ?
N1 C12 C13 . . 110.7(4) ?
N1 C12 H12A . . 109.5 ?
C13 C12 H12A . . 109.5 ?
N1 C12 H12B . . 109.5 ?
C13 C12 H12B . . 109.5 ?
H12A C12 H12B . . 108.1 ?
C5 C4 C3 . . 121.6(4) ?
C5 C4 H4 . . 119.2 ?
C3 C4 H4 . . 119.2 ?
C4 C5 C6 . . 122.9(4) ?
C4 C5 H5 . . 118.6 ?
C6 C5 H5 . . 118.6 ?
C7 C8 C9 . . 118.3(4) ?
C7 C8 H8 . . 120.8 ?
C9 C8 H8 . . 120.8 ?
C8 C7 C6 . . 122.6(4) ?
C8 C7 H7 . . 118.7 ?
C6 C7 H7 . . 118.7 ?
C10 C9 C8 . . 120.9(5) ?
C10 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
O2 C13 C12 . . 106.9(4) ?
O2 C13 H13A . . 110.3 ?
C12 C13 H13A . . 110.3 ?
O2 C13 H13B . . 110.3 ?
C12 C13 H13B . . 110.3 ?
H13A C13 H13B . . 108.6 ?
O2 C14 C14 . 2_565 108.7(3) ?
O2 C14 H14A . . 109.9 ?
C14 C14 H14A 2_565 . 109.9 ?
O2 C14 H14B . . 109.9 ?
C14 C14 H14B 2_565 . 109.9 ?
H14A C14 H14B . . 108.3 ?
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 . 1.294(4) ?
N1 C12 . 1.444(5) ?
N1 H1A . 0.8600 ?
C2 C1 . 1.410(5) ?
C2 C3 . 1.426(5) ?
C2 C11 . 1.447(5) ?
O1 C3 . 1.276(5) ?
O2 C14 . 1.410(5) ?
O2 C13 . 1.420(5) ?
C11 C10 . 1.402(5) ?
C11 C6 . 1.415(5) ?
C1 H1 . 0.9300 ?
C6 C7 . 1.394(6) ?
C6 C5 . 1.429(6) ?
C3 C4 . 1.434(6) ?
C10 C9 . 1.365(5) ?
C10 H10 . 0.9300 ?
C12 C13 . 1.494(6) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C4 C5 . 1.331(6) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C8 C7 . 1.354(7) ?
C8 C9 . 1.390(6) ?
C8 H8 . 0.9300 ?
C7 H7 . 0.9300 ?
C9 H9 . 0.9300 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C14 2_565 1.486(8) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
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
N1 H1A O1 . 0.86 1.85 2.542(5) 136
C14 H14B O2 7_566 0.97 2.58 3.382(5) 141
C12 H12B O1 1_545 0.97 2.50 3.257(5) 134
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
C1 C2 C11 C10 . . . . -5.6(6) ?
C3 C2 C11 C10 . . . . 177.6(4) ?
C1 C2 C11 C6 . . . . 175.9(4) ?
C3 C2 C11 C6 . . . . -0.9(6) ?
C12 N1 C1 C2 . . . . 177.0(4) ?
C3 C2 C1 N1 . . . . -3.4(6) ?
C11 C2 C1 N1 . . . . 179.8(4) ?
C10 C11 C6 C7 . . . . 1.5(6) ?
C2 C11 C6 C7 . . . . -179.9(4) ?
C10 C11 C6 C5 . . . . -179.5(4) ?
C2 C11 C6 C5 . . . . -0.9(6) ?
C1 C2 C3 O1 . . . . 5.5(6) ?
C11 C2 C3 O1 . . . . -177.7(4) ?
C1 C2 C3 C4 . . . . -175.0(4) ?
C11 C2 C3 C4 . . . . 1.8(6) ?
C6 C11 C10 C9 . . . . -1.3(6) ?
C2 C11 C10 C9 . . . . -179.8(4) ?
C1 N1 C12 C13 . . . . -140.1(4) ?
O1 C3 C4 C5 . . . . 178.5(4) ?
C2 C3 C4 C5 . . . . -1.1(7) ?
C3 C4 C5 C6 . . . . -0.8(7) ?
C7 C6 C5 C4 . . . . -179.3(5) ?
C11 C6 C5 C4 . . . . 1.8(7) ?
C9 C8 C7 C6 . . . . 0.3(7) ?
C11 C6 C7 C8 . . . . -1.1(7) ?
C5 C6 C7 C8 . . . . 180.0(4) ?
C11 C10 C9 C8 . . . . 0.5(7) ?
C7 C8 C9 C10 . . . . 0.0(7) ?
C14 O2 C13 C12 . . . . 179.6(3) ?
N1 C12 C13 O2 . . . . -61.2(5) ?
C13 O2 C14 C14 . . . 2_565 -179.5(4) ?
