#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:28:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178813 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/67/4106775.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_4106775
loop_
_publ_author_name
'Mikihiro Hayashi'
'Fumiyuki Toshimitsu'
'Ryota Sakamoto'
'Hiroshi Nishihara'
_publ_section_title
;
 Double Lactonization in Triarylamine-Conjugated Dimethyl
 Diethynylfumarate: Formation of Intensely Colored and Luminescent
 Quadrupolar Molecules Including a Missing Structural Isomer of Pechmann
 Dyes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14518
_journal_page_last               14521
_journal_paper_doi               10.1021/ja2054176
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C48 H38 N2 O8'
_chemical_formula_sum            'C48 H38 N2 O8'
_chemical_formula_weight         770.8
_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'
_audit_creation_date             2011-05-02T21:44:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 109.689(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.930(4)
_cell_length_b                   10.396(3)
_cell_length_c                   14.846(5)
_cell_measurement_reflns_used    4143
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      3.168
_cell_volume                     1878.9(10)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
        ????
;
_diffrn_ambient_temperature      113
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device
;
        Saturn724 (4x4 bin mode)
;
_diffrn_measurement_method       dtintegrate.ref
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11772
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.9
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.404
_refine_diff_density_min         -0.529
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_gt           0.0862
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1410P)²+2.3550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.247
_reflns_number_gt                2787
_reflns_number_total             3296
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2054176_si_004.cif
_cod_data_source_block           p66-1
_cod_database_code               4106775
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_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_calc_flag
_atom_site_refinement_flags
O1 O 0.0112(2) 0.6276(2) 0.88197(17) 0.0407(7) Uani 1 d .
O2 O 0.3067(2) -0.1385(3) 1.23900(18) 0.0459(7) Uani 1 d .
O3 O 0.4582(2) 0.1688(3) 0.59950(18) 0.0456(7) Uani 1 d .
O4 O 0.5354(3) 0.2810(3) 0.5110(2) 0.0592(9) Uani 1 d .
N1 N 0.2079(2) 0.1460(3) 0.90087(18) 0.0293(6) Uani 1 d .
C1 C 0.1549(3) 0.2671(3) 0.8987(2) 0.0263(7) Uani 1 d .
C2 C 0.0716(3) 0.3073(3) 0.8162(2) 0.0290(7) Uani 1 d .
H2 H 0.0477 0.2525 0.7619 0.035 Uiso 1 calc R
C3 C 0.0237(3) 0.4270(3) 0.8134(2) 0.0307(7) Uani 1 d .
H3 H -0.0326 0.4544 0.7569 0.037 Uiso 1 calc R
C4 C 0.0581(3) 0.5080(3) 0.8934(2) 0.0306(7) Uani 1 d .
C5 C 0.1374(3) 0.4658(3) 0.9768(2) 0.0321(7) Uani 1 d .
H5 H 0.1593 0.5188 1.0321 0.039 Uiso 1 calc R
C6 C 0.1845(3) 0.3457(3) 0.9787(2) 0.0298(7) Uani 1 d .
H6 H 0.2383 0.3167 1.0361 0.036 Uiso 1 calc R
C7 C 0.0596(4) 0.7205(3) 0.9544(3) 0.0477(10) Uani 1 d .
H7A H 0.0447 0.6971 1.0128 0.057 Uiso 1 calc R
H7B H 0.0282 0.8054 0.9326 0.057 Uiso 1 calc R
H7C H 0.1391 0.7228 0.9677 0.057 Uiso 1 calc R
C8 C 0.2316(3) 0.0692(3) 0.9857(2) 0.0291(7) Uani 1 d .
C9 C 0.3361(3) 0.0205(3) 1.0321(2) 0.0344(8) Uani 1 d .
H9 H 0.3933 0.0356 1.0066 0.041 Uiso 1 calc R
C10 C 0.3573(3) -0.0503(3) 1.1158(2) 0.0374(8) Uani 1 d .
H10 H 0.4283 -0.0856 1.1462 0.045 Uiso 1 calc R
C11 C 0.2757(3) -0.0695(3) 1.1551(2) 0.0346(8) Uani 1 d .
C12 C 0.1712(3) -0.0209(3) 1.1098(2) 0.0339(8) Uani 1 d .
H12 H 0.1148 -0.0336 1.1365 0.041 Uiso 1 calc R
C13 C 0.1500(3) 0.0469(3) 1.0244(2) 0.0318(8) Uani 1 d .
H13 H 0.078 0.0784 0.9923 0.038 Uiso 1 calc R
C14 C 0.2297(3) -0.1467(4) 1.2877(3) 0.0483(10) Uani 1 d .
H14A H 0.1638 -0.1919 1.2474 0.058 Uiso 1 calc R
H14B H 0.2097 -0.0599 1.3017 0.058 Uiso 1 calc R
H14C H 0.2623 -0.1941 1.3477 0.058 Uiso 1 calc R
C15 C 0.2647(3) 0.1244(3) 0.8355(2) 0.0278(7) Uani 1 d .
C16 C 0.2989(3) 0.2254(3) 0.7918(2) 0.0299(7) Uani 1 d .
H16 H 0.2854 0.3113 0.8065 0.036 Uiso 1 calc R
C17 C 0.3526(2) 0.2029(3) 0.7266(2) 0.0294(7) Uani 1 d .
H17 H 0.3757 0.2734 0.6974 0.035 Uiso 1 calc R
C18 C 0.3730(3) 0.0769(3) 0.7034(2) 0.0292(7) Uani 1 d .
C19 C 0.3394(3) -0.0241(3) 0.7486(2) 0.0330(8) Uani 1 d .
H19 H 0.3528 -0.1103 0.7342 0.04 Uiso 1 calc R
C20 C 0.2870(3) -0.0011(3) 0.8140(2) 0.0316(8) Uani 1 d .
H20 H 0.2659 -0.0715 0.8447 0.038 Uiso 1 calc R
C21 C 0.4244(3) 0.0536(3) 0.6308(2) 0.0312(7) Uani 1 d .
C22 C 0.4340(3) -0.0598(4) 0.5917(3) 0.0465(10) Uani 1 d .
H22 H 0.4109 -0.1379 0.6123 0.056 Uiso 1 calc R
C23 C 0.5051(3) 0.1774(4) 0.5293(3) 0.0430(9) Uani 1 d .
C24 C 0.5162(3) 0.0565(3) 0.4874(3) 0.0376(8) Uani 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 0 '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 0.006 '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
C4 O1 C7 117.3(3) . .
C11 O2 C14 117.0(3) . .
C23 O3 C21 124.9(3) . .
C15 N1 C1 118.6(2) . .
C15 N1 C8 120.4(2) . .
C1 N1 C8 118.0(2) . .
C6 C1 C2 118.9(3) . .
C6 C1 N1 120.6(3) . .
C2 C1 N1 120.4(3) . .
C3 C2 C1 120.1(3) . .
C3 C2 H2 120 . .
C1 C2 H2 120 . .
C2 C3 C4 120.3(3) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.9 . .
O1 C4 C5 124.2(3) . .
O1 C4 C3 116.1(3) . .
C5 C4 C3 119.7(3) . .
C6 C5 C4 119.4(3) . .
C6 C5 H5 120.3 . .
C4 C5 H5 120.3 . .
C1 C6 C5 121.5(3) . .
C1 C6 H6 119.3 . .
C5 C6 H6 119.3 . .
O1 C7 H7A 109.5 . .
O1 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
O1 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C13 C8 C9 118.9(3) . .
C13 C8 N1 119.5(3) . .
C9 C8 N1 121.5(3) . .
C10 C9 C8 120.1(3) . .
C10 C9 H9 119.9 . .
C8 C9 H9 119.9 . .
C11 C10 C9 120.4(3) . .
C11 C10 H10 119.8 . .
C9 C10 H10 119.8 . .
O2 C11 C10 115.3(3) . .
O2 C11 C12 124.7(3) . .
C10 C11 C12 120.0(3) . .
C11 C12 C13 119.1(3) . .
C11 C12 H12 120.4 . .
C13 C12 H12 120.4 . .
C8 C13 C12 121.3(3) . .
C8 C13 H13 119.3 . .
C12 C13 H13 119.3 . .
O2 C14 H14A 109.5 . .
O2 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
O2 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C16 C15 C20 118.5(3) . .
C16 C15 N1 121.5(3) . .
C20 C15 N1 120.0(3) . .
C15 C16 C17 120.9(3) . .
C15 C16 H16 119.5 . .
C17 C16 H16 119.5 . .
C16 C17 C18 120.5(3) . .
C16 C17 H17 119.7 . .
C18 C17 H17 119.7 . .
C19 C18 C17 118.1(3) . .
C19 C18 C21 121.5(3) . .
C17 C18 C21 120.3(3) . .
C20 C19 C18 121.0(3) . .
C20 C19 H19 119.5 . .
C18 C19 H19 119.5 . .
C19 C20 C15 120.8(3) . .
C19 C20 H20 119.6 . .
C15 C20 H20 119.6 . .
C22 C21 O3 121.5(3) . .
C22 C21 C18 126.6(3) . .
O3 C21 C18 111.8(3) . .
C21 C22 C24 116.2(4) . 3_656
C21 C22 H22 121.9 . .
C24 C22 H22 121.9 3_656 .
O4 C23 O3 119.2(3) . .
O4 C23 C24 126.7(3) . .
O3 C23 C24 114.0(3) . .
C24 C24 C23 124.1(5) 3_656 .
C24 C24 C22 119.3(4) 3_656 3_656
C23 C24 C22 116.6(3) . 3_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.368(4) .
O1 C7 1.423(5) .
O2 C11 1.375(4) .
O2 C14 1.416(4) .
O3 C23 1.374(4) .
O3 C21 1.406(4) .
O4 C23 1.208(4) .
N1 C15 1.418(4) .
N1 C1 1.428(4) .
N1 C8 1.434(4) .
C1 C6 1.385(4) .
C1 C2 1.396(4) .
C2 C3 1.384(4) .
C2 H2 0.95 .
C3 C4 1.400(4) .
C3 H3 0.95 .
C4 C5 1.386(5) .
C5 C6 1.386(5) .
C5 H5 0.95 .
C6 H6 0.95 .
C7 H7A 0.98 .
C7 H7B 0.98 .
C7 H7C 0.98 .
C8 C13 1.380(4) .
C8 C9 1.390(5) .
C9 C10 1.389(5) .
C9 H9 0.95 .
C10 C11 1.381(5) .
C10 H10 0.95 .
C11 C12 1.386(5) .
C12 C13 1.394(5) .
C12 H12 0.95 .
C13 H13 0.95 .
C14 H14A 0.98 .
C14 H14B 0.98 .
C14 H14C 0.98 .
C15 C16 1.384(5) .
C15 C20 1.396(4) .
C16 C17 1.388(4) .
C16 H16 0.95 .
C17 C18 1.401(5) .
C17 H17 0.95 .
C18 C19 1.392(5) .
C18 C21 1.464(4) .
C19 C20 1.379(4) .
C19 H19 0.95 .
C20 H20 0.95 .
C21 C22 1.339(5) .
C22 C24 1.518(6) 3_656
C22 H22 0.95 .
C23 C24 1.431(5) .
C24 C24 1.342(7) 3_656
C24 C22 1.518(6) 3_656
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_4
C15 N1 C1 C6 -120.1(3) .
C8 N1 C1 C6 40.4(4) .
C15 N1 C1 C2 60.6(4) .
C8 N1 C1 C2 -138.9(3) .
C6 C1 C2 C3 3.3(5) .
N1 C1 C2 C3 -177.4(3) .
C1 C2 C3 C4 -0.4(5) .
C7 O1 C4 C5 10.6(5) .
C7 O1 C4 C3 -167.7(3) .
C2 C3 C4 O1 175.9(3) .
C2 C3 C4 C5 -2.4(5) .
O1 C4 C5 C6 -175.9(3) .
C3 C4 C5 C6 2.3(5) .
C2 C1 C6 C5 -3.4(5) .
N1 C1 C6 C5 177.2(3) .
C4 C5 C6 C1 0.6(5) .
C15 N1 C8 C13 -150.6(3) .
C1 N1 C8 C13 49.3(4) .
C15 N1 C8 C9 31.9(5) .
C1 N1 C8 C9 -128.2(3) .
C13 C8 C9 C10 0.5(5) .
N1 C8 C9 C10 178.0(3) .
C8 C9 C10 C11 -2.0(5) .
C14 O2 C11 C10 172.4(3) .
C14 O2 C11 C12 -7.9(5) .
C9 C10 C11 O2 -178.6(3) .
C9 C10 C11 C12 1.6(5) .
O2 C11 C12 C13 -179.6(3) .
C10 C11 C12 C13 0.1(5) .
C9 C8 C13 C12 1.3(5) .
N1 C8 C13 C12 -176.3(3) .
C11 C12 C13 C8 -1.6(5) .
C1 N1 C15 C16 20.1(4) .
C8 N1 C15 C16 -139.9(3) .
C1 N1 C15 C20 -159.8(3) .
C8 N1 C15 C20 40.2(4) .
C20 C15 C16 C17 1.1(5) .
N1 C15 C16 C17 -178.8(3) .
C15 C16 C17 C18 0.2(5) .
C16 C17 C18 C19 -0.9(5) .
C16 C17 C18 C21 176.7(3) .
C17 C18 C19 C20 0.3(5) .
C21 C18 C19 C20 -177.3(3) .
C18 C19 C20 C15 1.1(5) .
C16 C15 C20 C19 -1.7(5) .
N1 C15 C20 C19 178.2(3) .
C23 O3 C21 C22 -1.3(5) .
C23 O3 C21 C18 -177.4(3) .
C19 C18 C21 C22 8.1(6) .
C17 C18 C21 C22 -169.4(3) .
C19 C18 C21 O3 -176.1(3) .
C17 C18 C21 O3 6.4(4) .
O3 C21 C22 C24 0.4(5) 3_656
C18 C21 C22 C24 175.8(3) 3_656
C21 O3 C23 O4 -176.8(3) .
C21 O3 C23 C24 1.0(5) .
O4 C23 C24 C24 178.0(5) 3_656
O3 C23 C24 C24 0.4(6) 3_656
O4 C23 C24 C22 -3.2(6) 3_656
O3 C23 C24 C22 179.2(3) 3_656
