#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:28:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178813 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/67/4106774.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_4106774
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             2011-05-02T22:45:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 109.883(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.985(4)
_cell_length_b                   10.427(3)
_cell_length_c                   14.899(4)
_cell_measurement_reflns_used    3957
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.4913
_cell_measurement_theta_min      3.2193
_cell_volume                     1897.0(9)
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0416
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14566
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.9001
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       Block
_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         0.323
_refine_diff_density_min         -0.443
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_gt           0.0814
_refine_ls_shift/su_max          0.024
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0353P)²+3.1319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1811
_reflns_number_gt                3159
_reflns_number_total             4296
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2054176_si_003.cif
_cod_data_source_block           p56
_cod_original_cell_volume        1896.9(9)
_cod_database_code               4106774
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
_atom_site_disorder_group
_atom_site_disorder_assembly
C21A C 0.4184(7) 0.0312(8) 0.6353(6) 0.0223(16) Uani 0.5 d P 1 A
C22A C 0.4268(5) -0.0908(6) 0.6020(4) 0.0280(14) Uani 0.5 d P 1 A
H22A H 0.4023 -0.1644 0.6264 0.034 Uiso 0.5 calc PR 1 A
C23 C 0.4726(5) -0.0995(6) 0.5318(4) 0.0337(14) Uani 0.5 d P 1 .
C25A C 0.4987(5) 0.1324(8) 0.5257(4) 0.0366(15) Uani 0.5 d P 1 .
O3A O 0.4534(5) 0.1333(6) 0.6000(5) 0.0415(15) Uani 0.5 d P 1 A
O4A O 0.5260(9) 0.2309(10) 0.4974(7) 0.082(4) Uani 0.5 d P 1 .
C21B C 0.4088(8) -0.0275(10) 0.6362(8) 0.041(3) Uani 0.5 d P 2 A
H21B H 0.4055 -0.1185 0.6334 0.049 Uiso 0.5 calc PR 2 A
C22B C 0.4509(5) 0.0376(7) 0.5808(5) 0.0316(13) Uani 0.5 d P 2 A
C25B C 0.5141(8) 0.2181(15) 0.5147(8) 0.0291(19) Uiso 0.5 d P 2 A
O3B O 0.4577(6) 0.1725(6) 0.5836(5) 0.0342(18) Uiso 0.5 d P 2 A
O4B O 0.5251(4) 0.3243(6) 0.5073(4) 0.0518(13) Uiso 0.5 d P 2 A
C24 C 0.5 0 0.5 0.0399(11) Uani 1 d S . .
O1 O 0.0098(2) 0.6238(2) 0.88077(15) 0.0396(6) Uani 1 d . . .
O2 O 0.3097(2) -0.1254(2) 1.24730(17) 0.0459(6) Uani 1 d . . .
N1 N 0.2068(2) 0.1435(2) 0.90337(17) 0.0316(6) Uani 1 d . . .
C1 C 0.1554(2) 0.2659(3) 0.89992(19) 0.0266(6) Uani 1 d . . .
C2 C 0.0722(2) 0.3046(3) 0.8175(2) 0.0295(6) Uani 1 d . . .
H2 H 0.0485 0.2492 0.7637 0.035 Uiso 1 calc R . .
C3 C 0.0239(2) 0.4234(3) 0.8136(2) 0.0316(7) Uani 1 d . . .
H3 H -0.0327 0.4496 0.7571 0.038 Uiso 1 calc R . .
C4 C 0.0578(2) 0.5054(3) 0.8927(2) 0.0297(6) Uani 1 d . . .
C5 C 0.1378(2) 0.4650(3) 0.9762(2) 0.0306(6) Uani 1 d . . .
H5 H 0.1596 0.5184 1.0311 0.037 Uiso 1 calc R . .
C6 C 0.1856(2) 0.3448(3) 0.97836(19) 0.0284(6) Uani 1 d . . .
H6 H 0.2403 0.3169 1.0355 0.034 Uiso 1 calc R . .
C7 C 0.0583(3) 0.7177(3) 0.9525(2) 0.0488(9) Uani 1 d . . .
H7A H 0.0472 0.693 1.012 0.059 Uiso 1 calc R . .
H7B H 0.024 0.8013 0.9314 0.059 Uiso 1 calc R . .
H7C H 0.1369 0.7233 0.9633 0.059 Uiso 1 calc R . .
C8 C 0.2308(2) 0.0701(3) 0.9890(2) 0.0288(6) Uani 1 d . . .
C9 C 0.3356(3) 0.0235(3) 1.0374(2) 0.0392(8) Uani 1 d . . .
H9 H 0.3923 0.0372 1.0117 0.047 Uiso 1 calc R . .
C10 C 0.3578(3) -0.0417(3) 1.1215(2) 0.0383(7) Uani 1 d . . .
H10 H 0.4294 -0.0742 1.1528 0.046 Uiso 1 calc R . .
C11 C 0.2775(2) -0.0609(3) 1.1613(2) 0.0314(7) Uani 1 d . . .
C12 C 0.1728(3) -0.0151(3) 1.1148(2) 0.0352(7) Uani 1 d . . .
H12 H 0.117 -0.027 1.1419 0.042 Uiso 1 calc R . .
C13 C 0.1497(2) 0.0484(3) 1.0281(2) 0.0332(7) Uani 1 d . . .
H13 H 0.0772 0.0773 0.9952 0.04 Uiso 1 calc R . .
C14 C 0.2336(3) -0.1325(4) 1.2956(3) 0.0591(11) Uani 1 d . . .
H14A H 0.1675 -0.1771 1.2555 0.071 Uiso 1 calc R . .
H14B H 0.2142 -0.0456 1.3094 0.071 Uiso 1 calc R . .
H14C H 0.266 -0.1796 1.3556 0.071 Uiso 1 calc R . .
C15 C 0.2602(2) 0.1141(3) 0.8381(2) 0.0327(7) Uani 1 d . . A
C16 C 0.2955(2) 0.2089(4) 0.7893(2) 0.0372(7) Uani 1 d . . .
H16 H 0.2838 0.2966 0.8001 0.045 Uiso 1 calc R . .
C17 C 0.3476(2) 0.1763(4) 0.7249(2) 0.0448(9) Uani 1 d . . A
H17 H 0.3719 0.2421 0.6929 0.054 Uiso 1 calc R . .
C18 C 0.3646(3) 0.0474(4) 0.7067(2) 0.0489(10) Uani 1 d . . .
C19 C 0.3296(3) -0.0455(4) 0.7562(2) 0.0496(10) Uani 1 d . . A
H19 H 0.3409 -0.1333 0.7455 0.06 Uiso 1 calc R . .
C20 C 0.2788(3) -0.0137(4) 0.8205(2) 0.0406(8) Uani 1 d . . .
H20 H 0.2562 -0.0798 0.8535 0.049 Uiso 1 calc R . A
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
O3A C21A C22A 120.8(6) . .
O3A C21A C18 120.3(7) . .
C22A C21A C18 118.8(6) . .
C23 C22A C21A 116.3(6) . .
C23 C22A H22A 121.9 . .
C21A C22A H22A 121.9 . .
C25A C23 C24 75.3(6) 3_656 .
C25A C23 C22A 164.9(8) 3_656 .
C24 C23 C22A 119.4(5) . .
C25A C23 O4A 54.8(6) 3_656 3_656
C24 C23 O4A 130.1(6) . 3_656
C22A C23 O4A 110.3(6) . 3_656
C23 C25A O4A 77.1(7) 3_656 .
C23 C25A O3A 161.9(9) 3_656 .
O4A C25A O3A 120.9(9) . .
C23 C25A C24 56.9(5) 3_656 .
O4A C25A C24 134.0(7) . .
O3A C25A C24 105.1(5) . .
C21A O3A C25A 126.2(7) . .
C25A O4A C23 48.0(6) . 3_656
C22B C21B C18 119.1(8) . .
C22B C21B H21B 120.4 . .
C18 C21B H21B 120.4 . .
C21B C22B O3B 121.9(8) . .
C21B C22B C24 134.7(7) . .
O3B C22B C24 103.4(5) . .
O4B C25B O3B 118.5(10) . .
C22B O3B C25B 109.3(8) . .
C23 C24 C23 180.0(3) 3_656 .
C23 C24 C25A 132.2(4) 3_656 3_656
C23 C24 C25A 47.8(4) . 3_656
C23 C24 C25A 47.8(4) 3_656 .
C23 C24 C25A 132.2(4) . .
C25A C24 C25A 180.0(5) 3_656 .
C23 C24 C22B 71.1(4) 3_656 3_656
C23 C24 C22B 108.9(4) . 3_656
C25A C24 C22B 61.1(3) 3_656 3_656
C25A C24 C22B 118.9(3) . 3_656
C23 C24 C22B 108.9(4) 3_656 .
C23 C24 C22B 71.1(4) . .
C25A C24 C22B 118.9(3) 3_656 .
C25A C24 C22B 61.1(3) . .
C22B C24 C22B 180.0(2) 3_656 .
C4 O1 C7 117.2(3) . .
C11 O2 C14 117.1(3) . .
C15 N1 C8 119.5(2) . .
C15 N1 C1 120.1(2) . .
C8 N1 C1 117.8(2) . .
C6 C1 C2 119.2(3) . .
C6 C1 N1 120.6(3) . .
C2 C1 N1 120.2(3) . .
C3 C2 C1 120.1(3) . .
C3 C2 H2 119.9 . .
C1 C2 H2 119.9 . .
C2 C3 C4 120.3(3) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.9 . .
O1 C4 C5 124.0(3) . .
O1 C4 C3 116.3(3) . .
C5 C4 C3 119.7(3) . .
C4 C5 C6 119.0(3) . .
C4 C5 H5 120.5 . .
C6 C5 H5 120.5 . .
C1 C6 C5 121.5(3) . .
C1 C6 H6 119.2 . .
C5 C6 H6 119.2 . .
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 118.3(3) . .
C13 C8 N1 119.8(3) . .
C9 C8 N1 121.9(3) . .
C10 C9 C8 120.9(3) . .
C10 C9 H9 119.6 . .
C8 C9 H9 119.6 . .
C9 C10 C11 120.7(3) . .
C9 C10 H10 119.6 . .
C11 C10 H10 119.6 . .
C10 C11 O2 115.8(3) . .
C10 C11 C12 119.5(3) . .
O2 C11 C12 124.7(3) . .
C11 C12 C13 119.6(3) . .
C11 C12 H12 120.2 . .
C13 C12 H12 120.2 . .
C8 C13 C12 120.9(3) . .
C8 C13 H13 119.5 . .
C12 C13 H13 119.5 . .
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 118.1(3) . .
C16 C15 N1 122.2(3) . .
C20 C15 N1 119.7(3) . .
C17 C16 C15 120.7(3) . .
C17 C16 H16 119.7 . .
C15 C16 H16 119.7 . .
C16 C17 C18 120.8(3) . .
C16 C17 H17 119.6 . .
C18 C17 H17 119.6 . .
C19 C18 C17 117.7(3) . .
C19 C18 C21A 129.0(5) . .
C17 C18 C21A 113.3(5) . .
C19 C18 C21B 105.7(5) . .
C17 C18 C21B 136.5(5) . .
C21A C18 C21B 23.5(3) . .
C20 C19 C18 121.6(4) . .
C20 C19 H19 119.2 . .
C18 C19 H19 119.2 . .
C19 C20 C15 121.0(4) . .
C19 C20 H20 119.5 . .
C15 C20 H20 119.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C21A O3A 1.334(10) .
C21A C22A 1.384(9) .
C21A C18 1.467(8) .
C22A C23 1.370(8) .
C22A H22A 0.95 .
C23 C25A 1.098(8) 3_656
C23 C24 1.242(6) .
C23 O4A 1.440(13) 3_656
C25A C23 1.098(8) 3_656
C25A O4A 1.208(12) .
C25A O3A 1.420(9) .
C25A C24 1.434(8) .
O4A C23 1.440(13) 3_656
C21B C22B 1.322(11) .
C21B C18 1.566(13) .
C21B H21B 0.95 .
C22B O3B 1.410(8) .
C22B C24 1.591(7) .
C25B O4B 1.126(17) .
C25B O3B 1.526(13) .
C24 C23 1.242(6) 3_656
C24 C25A 1.434(8) 3_656
C24 C22B 1.591(7) 3_656
O1 C4 1.368(4) .
O1 C7 1.428(4) .
O2 C11 1.380(4) .
O2 C14 1.409(4) .
N1 C15 1.406(4) .
N1 C8 1.428(4) .
N1 C1 1.433(4) .
C1 C6 1.373(4) .
C1 C2 1.392(4) .
C2 C3 1.381(4) .
C2 H2 0.95 .
C3 C4 1.399(4) .
C3 H3 0.95 .
C4 C5 1.387(4) .
C5 C6 1.394(4) .
C5 H5 0.95 .
C6 H6 0.95 .
C7 H7A 0.98 .
C7 H7B 0.98 .
C7 H7C 0.98 .
C8 C13 1.384(4) .
C8 C9 1.393(4) .
C9 C10 1.366(4) .
C9 H9 0.95 .
C10 C11 1.379(4) .
C10 H10 0.95 .
C11 C12 1.384(4) .
C12 C13 1.390(4) .
C12 H12 0.95 .
C13 H13 0.95 .
C14 H14A 0.98 .
C14 H14B 0.98 .
C14 H14C 0.98 .
C15 C16 1.394(5) .
C15 C20 1.395(5) .
C16 C17 1.391(4) .
C16 H16 0.95 .
C17 C18 1.403(6) .
C17 H17 0.95 .
C18 C19 1.384(6) .
C19 C20 1.376(4) .
C19 H19 0.95 .
C20 H20 0.95 .
