#------------------------------------------------------------------------------
#$Date: 2015-06-05 02:56:31 +0300 (Fri, 05 Jun 2015) $
#$Revision: 138039 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/29/4512954.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_4512954
loop_
_publ_author_name
'Kohmoto, Shigeo'
'Chuko, Tomotaka'
'Hisamatsu, Shugo'
'Okuda, Yasuhiro'
'Masu, Hyuma'
'Takahashi, Masahiro'
'Kishikawa, Keiki'
_publ_section_title
;
 Piezoluminescence and Liquid Crystallinity of
 4,4′-(9,10-Anthracenediyl)bispyridinium Salts
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2723
_journal_paper_doi               10.1021/acs.cgd.5b00028
_journal_volume                  15
_journal_year                    2015
_chemical_formula_sum            'C48 H50 Cl2 N2 O8'
_chemical_formula_weight         853.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 126.2930(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.258(2)
_cell_length_b                   8.1420(6)
_cell_length_c                   22.6504(17)
_cell_measurement_temperature    173.(2)
_cell_volume                     4349.0(5)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173.(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'graphite '
_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11845
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.23
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.389
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0397
_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)+(0.0475P)²+3.9260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1090
_reflns_number_gt                4044
_reflns_number_total             4895
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5b00028_si_002.cif
_cod_data_source_block           1/1a(EtOAc)_a130722his2
_cod_depositor_comments
'Adding full bibliography for 4512954--4512957.cif.'
_cod_original_cell_volume        4349.0(6)
_cod_database_code               4512954
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C26 0.4574(3) 0.0641(10) 0.3747(3) 0.079(2) Uani d . P . 0.5 A -2
H H26A 0.4407 -0.0456 0.3654 0.119 Uiso calc U P R 0.5 A -2
H H26B 0.4689 0.0835 0.3425 0.119 Uiso calc U P R 0.5 A -2
H H26C 0.4294 0.1468 0.3651 0.119 Uiso calc U P R 0.5 A -2
C C25 0.50799(19) 0.0759(6) 0.4527(2) 0.0552(10) Uani d . P . 0.5 A -2
H H25A 0.5409 0.0252 0.4577 0.066 Uiso calc U P R 0.5 A -2
H H25B 0.517 0.1931 0.4664 0.066 Uiso calc U P R 0.5 A -2
C C23 0.4865(3) 0.0536(9) 0.3870(4) 0.0696(17) Uani d . P . 0.5 A -1
H H23A 0.4592 0.0253 0.3351 0.104 Uiso calc U P R 0.5 A -1
H H23B 0.5238 0.0092 0.4053 0.104 Uiso calc U P R 0.5 A -1
H H23C 0.4889 0.1733 0.3926 0.104 Uiso calc U P R 0.5 A -1
C C24 0.46729(17) -0.0182(5) 0.4298(2) 0.0476(9) Uani d . P . 0.5 A -1
O O5 0.42000(12) -0.0643(4) 0.40328(17) 0.0551(7) Uani d . P . 0.5 A -1
C C1 0.45353(7) 0.3777(2) 0.57204(9) 0.0362(4) Uani d . . . 1 . .
H H1 0.414 0.3576 0.5452 0.043 Uiso calc U . R 1 . .
C C2 0.48782(7) 0.3481(2) 0.64526(9) 0.0395(4) Uani d . . . 1 . .
H H2 0.4722 0.3052 0.6687 0.047 Uiso calc U . R 1 . .
C C3 0.54676(7) 0.3808(2) 0.68690(9) 0.0368(4) Uani d . . . 1 . .
H H3 0.5703 0.3598 0.7381 0.044 Uiso calc U . R 1 . .
C C4 0.56995(6) 0.4419(2) 0.65438(9) 0.0328(3) Uani d . . . 1 . .
H H4 0.6093 0.4661 0.6834 0.039 Uiso calc U . R 1 . .
C C5 0.53596(6) 0.47035(19) 0.57689(8) 0.0294(3) Uani d . . . 1 . .
C C6 0.47586(6) 0.43836(19) 0.53467(9) 0.0303(3) Uani d . . . 1 . .
C C7 0.44131(6) 0.46903(19) 0.45871(9) 0.0293(3) Uani d . . . 1 . .
C C8 0.37879(6) 0.43836(19) 0.41466(8) 0.0274(3) Uani d . . . 1 . .
C C9 0.35704(6) 0.2800(2) 0.40087(9) 0.0338(3) Uani d . . . 1 . .
H H9 0.3821 0.1887 0.4211 0.041 Uiso calc U . R 1 . .
C C10 0.29933(6) 0.25472(19) 0.35803(9) 0.0314(3) Uani d . . . 1 . .
H H10 0.2848 0.146 0.348 0.038 Uiso calc U . R 1 . .
C C11 0.34039(6) 0.56788(18) 0.38501(8) 0.0282(3) Uani d . . . 1 . .
H H11 0.3538 0.6778 0.3936 0.034 Uiso calc U . R 1 . .
C C12 0.28298(6) 0.53782(19) 0.34326(8) 0.0280(3) Uani d . . . 1 . .
H H12 0.257 0.627 0.3235 0.034 Uiso calc U . R 1 . .
C C13 0.20097(6) 0.3523(2) 0.28351(8) 0.0299(3) Uani d . . . 1 . .
H H13A 0.1931 0.2387 0.2643 0.036 Uiso calc U . R 1 . .
H H13B 0.182 0.4286 0.2413 0.036 Uiso calc U . R 1 . .
C C14 0.17760(6) 0.37702(19) 0.32707(8) 0.0277(3) Uani d . . . 1 . .
C C15 0.18519(6) 0.25318(19) 0.37451(8) 0.0281(3) Uani d . . . 1 . .
H H15 0.2025 0.1523 0.3769 0.034 Uiso calc U . R 1 . .
C C16 0.16705(6) 0.27903(19) 0.41856(8) 0.0288(3) Uani d . . . 1 . .
C C17 0.14021(6) 0.4261(2) 0.41336(9) 0.0308(3) Uani d . . . 1 . .
C C18 0.13065(6) 0.5457(2) 0.36319(9) 0.0321(3) Uani d . . . 1 . .
C C19 0.15045(6) 0.5230(2) 0.32090(8) 0.0310(3) Uani d . . . 1 . .
H H19 0.1454 0.6064 0.2882 0.037 Uiso calc U . R 1 . .
C C20 0.20022(8) 0.0158(2) 0.47541(10) 0.0382(4) Uani d . . . 1 . .
H H20A 0.1783 -0.0398 0.4278 0.057 Uiso calc U . R 1 . .
H H20B 0.2011 -0.0528 0.5116 0.057 Uiso calc U . R 1 . .
H H20C 0.239 0.0345 0.4911 0.057 Uiso calc U . R 1 . .
C C21 0.15176(10) 0.5731(3) 0.51121(12) 0.0552(5) Uani d . . . 1 . .
H H21A 0.1926 0.5508 0.5411 0.083 Uiso calc U . R 1 . .
H H21B 0.1389 0.5743 0.5425 0.083 Uiso calc U . R 1 . .
H H21C 0.1441 0.6801 0.4872 0.083 Uiso calc U . R 1 . .
C C22 0.08513(8) 0.7991(2) 0.30392(10) 0.0475(5) Uani d . . . 1 . .
H H22A 0.1187 0.84 0.3087 0.071 Uiso calc U . R 1 . .
H H22B 0.0657 0.891 0.3084 0.071 Uiso calc U . R 1 . .
H H22C 0.0593 0.7468 0.256 0.071 Uiso calc U . R 1 . .
Cl Cl1 0.21480(2) 0.90299(5) 0.30004(2) 0.03535(12) Uani d . . . 1 . .
N N1 0.26360(5) 0.38243(15) 0.33040(6) 0.0248(3) Uani d . . . 1 . .
O O1 0.17430(5) 0.16976(14) 0.46918(7) 0.0373(3) Uani d . . . 1 . .
O O2 0.12208(5) 0.44788(15) 0.45683(7) 0.0391(3) Uani d . . . 1 . .
O O3 0.10210(5) 0.68220(15) 0.36026(7) 0.0432(3) Uani d . . . 1 . .
O O4 0.5 0 0.5 0.0945(10) Uani d . P S 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'
Cl Cl 0.1484 0.1585 '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
C25 C26 H26A . 109.5
C25 C26 H26B . 109.5
H26A C26 H26B . 109.5
C25 C26 H26C . 109.5
H26A C26 H26C . 109.5
H26B C26 H26C . 109.5
O4 C25 C26 . 112.8(5)
O4 C25 H25A . 109.0
C26 C25 H25A . 109.0
O4 C25 H25B . 109.0
C26 C25 H25B . 109.0
H25A C25 H25B . 107.8
C24 C23 H23A . 109.5
C24 C23 H23B . 109.5
H23A C23 H23B . 109.5
C24 C23 H23C . 109.5
H23A C23 H23C . 109.5
H23B C23 H23C . 109.5
O5 C24 O4 . 116.7(4)
O5 C24 C23 . 124.2(4)
O4 C24 C23 . 117.7(4)
C2 C1 C6 . 121.22(14)
C2 C1 H1 . 119.4
C6 C1 H1 . 119.4
C1 C2 C3 . 120.50(15)
C1 C2 H2 . 119.7
C3 C2 H2 . 119.7
C4 C3 C2 . 120.66(15)
C4 C3 H3 . 119.7
C2 C3 H3 . 119.7
C3 C4 C5 . 121.08(14)
C3 C4 H4 . 119.5
C5 C4 H4 . 119.5
C7 C5 C4 5_666 122.59(13)
C7 C5 C6 5_666 119.22(14)
C4 C5 C6 . 118.17(14)
C7 C6 C1 . 122.37(14)
C7 C6 C5 . 119.30(14)
C1 C6 C5 . 118.33(14)
C5 C7 C6 5_666 121.48(13)
C5 C7 C8 5_666 118.88(13)
C6 C7 C8 . 119.64(14)
C9 C8 C11 . 117.64(13)
C9 C8 C7 . 121.39(14)
C11 C8 C7 . 120.96(13)
C10 C9 C8 . 120.31(14)
C10 C9 H9 . 119.8
C8 C9 H9 . 119.8
N1 C10 C9 . 120.41(14)
N1 C10 H10 . 119.8
C9 C10 H10 . 119.8
C12 C11 C8 . 120.37(14)
C12 C11 H11 . 119.8
C8 C11 H11 . 119.8
N1 C12 C11 . 120.15(14)
N1 C12 H12 . 119.9
C11 C12 H12 . 119.9
N1 C13 C14 . 110.61(11)
N1 C13 H13A . 109.5
C14 C13 H13A . 109.5
N1 C13 H13B . 109.5
C14 C13 H13B . 109.5
H13A C13 H13B . 108.1
C19 C14 C15 . 121.17(14)
C19 C14 C13 . 120.08(14)
C15 C14 C13 . 118.73(14)
C14 C15 C16 . 119.21(14)
C14 C15 H15 . 120.4
C16 C15 H15 . 120.4
O1 C16 C15 . 124.49(14)
O1 C16 C17 . 115.43(14)
C15 C16 C17 . 120.07(14)
O2 C17 C18 . 121.09(14)
O2 C17 C16 . 118.96(14)
C18 C17 C16 . 119.92(14)
O3 C18 C17 . 115.42(14)
O3 C18 C19 . 124.36(15)
C17 C18 C19 . 120.21(15)
C14 C19 C18 . 119.30(15)
C14 C19 H19 . 120.4
C18 C19 H19 . 120.4
O1 C20 H20A . 109.5
O1 C20 H20B . 109.5
H20A C20 H20B . 109.5
O1 C20 H20C . 109.5
H20A C20 H20C . 109.5
H20B C20 H20C . 109.5
O2 C21 H21A . 109.5
O2 C21 H21B . 109.5
H21A C21 H21B . 109.5
O2 C21 H21C . 109.5
H21A C21 H21C . 109.5
H21B C21 H21C . 109.5
O3 C22 H22A . 109.5
O3 C22 H22B . 109.5
H22A C22 H22B . 109.5
O3 C22 H22C . 109.5
H22A C22 H22C . 109.5
H22B C22 H22C . 109.5
C10 N1 C12 . 121.11(12)
C10 N1 C13 . 119.58(13)
C12 N1 C13 . 119.31(12)
C16 O1 C20 . 117.68(12)
C17 O2 C21 . 114.38(13)
C18 O3 C22 . 117.71(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C26 C25 . 1.491(7)
C26 H26A . 0.98
C26 H26B . 0.98
C26 H26C . 0.98
C25 O4 . 1.372(5)
C25 H25A . 0.99
C25 H25B . 0.99
C23 C24 . 1.497(8)
C23 H23A . 0.98
C23 H23B . 0.98
C23 H23C . 0.98
C24 O5 . 1.197(5)
C24 O4 . 1.290(4)
C1 C2 . 1.358(2)
C1 C6 . 1.429(2)
C1 H1 . 0.95
C2 C3 . 1.417(2)
C2 H2 . 0.95
C3 C4 . 1.357(2)
C3 H3 . 0.95
C4 C5 . 1.434(2)
C4 H4 . 0.95
C5 C7 5_666 1.404(2)
C5 C6 . 1.443(2)
C6 C7 . 1.409(2)
C7 C5 5_666 1.404(2)
C7 C8 . 1.4978(19)
C8 C9 . 1.389(2)
C8 C11 . 1.390(2)
C9 C10 . 1.377(2)
C9 H9 . 0.95
C10 N1 . 1.3384(19)
C10 H10 . 0.95
C11 C12 . 1.377(2)
C11 H11 . 0.95
C12 N1 . 1.3460(19)
C12 H12 . 0.95
C13 N1 . 1.4974(17)
C13 C14 . 1.510(2)
C13 H13A . 0.99
C13 H13B . 0.99
C14 C19 . 1.390(2)
C14 C15 . 1.392(2)
C15 C16 . 1.396(2)
C15 H15 . 0.95
C16 O1 . 1.3649(19)
C16 C17 . 1.398(2)
C17 O2 . 1.3784(19)
C17 C18 . 1.393(2)
C18 O3 . 1.3680(19)
C18 C19 . 1.394(2)
C19 H19 . 0.95
C20 O1 . 1.428(2)
C20 H20A . 0.98
C20 H20B . 0.98
C20 H20C . 0.98
C21 O2 . 1.430(2)
C21 H21A . 0.98
C21 H21B . 0.98
C21 H21C . 0.98
C22 O3 . 1.425(2)
C22 H22A . 0.98
C22 H22B . 0.98
C22 H22C . 0.98
