#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:28:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178813 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/67/4106773.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_4106773
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         'C62 H54 N2 O8'
_chemical_formula_sum            'C62 H54 N2 O8'
_chemical_formula_weight         955.07
_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             2011-04-22T23:18:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 97.016(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.164(2)
_cell_length_b                   9.4753(18)
_cell_length_c                   23.560(5)
_cell_measurement_reflns_used    5762
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.5184
_cell_measurement_theta_min      3.0251
_cell_volume                     2473.6(8)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device
;
        Saturn724 (4x4 bin mode)
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19170
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.9004
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.259
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0606P)²+0.3517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                4509
_reflns_number_total             5646
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2054176_si_002.cif
_cod_data_source_block           auto
_cod_original_cell_volume        2473.6(9)
_cod_database_code               4106773
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
O001 O 0.58641(11) -0.05318(12) 0.45705(5) 0.0293(3) Uani 1 d .
O002 O 1.09827(10) -0.28867(12) 0.17540(5) 0.0277(3) Uani 1 d .
O003 O 0.26627(10) -0.00460(12) 0.00463(5) 0.0256(3) Uani 1 d .
O004 O 0.15084(11) 0.06859(14) -0.07534(5) 0.0332(3) Uani 1 d .
N005 N 0.64216(12) -0.13426(15) 0.22694(6) 0.0253(3) Uani 1 d .
C006 C 0.57971(14) 0.00878(17) 0.30526(7) 0.0235(4) Uani 1 d .
H006 H 0.5551 0.0819 0.2788 0.028 Uiso 1 calc R
C007 C 0.60376(14) -0.07994(17) 0.40149(7) 0.0226(3) Uani 1 d .
C008 C 0.77125(14) -0.30175(18) 0.18342(7) 0.0261(4) Uani 1 d .
H008 H 0.7028 -0.3593 0.1723 0.031 Uiso 1 calc R
C009 C 0.56682(14) 0.02602(17) 0.36227(7) 0.0235(3) Uani 1 d .
H009 H 0.5326 0.1105 0.3749 0.028 Uiso 1 calc R
C010 C 0.88369(15) -0.34274(17) 0.16980(7) 0.0252(4) Uani 1 d .
H010 H 0.8922 -0.4271 0.1489 0.03 Uiso 1 calc R
C011 C 0.56280(15) -0.09193(17) 0.12734(7) 0.0244(4) Uani 1 d .
H011 H 0.6423 -0.0901 0.1168 0.029 Uiso 1 calc R
C012 C 0.97100(15) -0.13637(18) 0.21789(7) 0.0247(4) Uani 1 d .
H012 H 1.04 -0.0807 0.2303 0.03 Uiso 1 calc R
C013 C 0.62865(14) -0.11554(17) 0.28612(7) 0.0224(3) Uani 1 d .
C014 C 0.75801(14) -0.17748(17) 0.21317(7) 0.0236(3) Uani 1 d .
C015 C 0.06068(14) -0.00733(17) 0.00912(7) 0.0234(3) Uani 1 d .
C016 C 0.98322(14) -0.25932(17) 0.18705(7) 0.0227(3) Uani 1 d .
C017 C 0.46465(15) -0.07125(17) 0.08630(7) 0.0241(3) Uani 1 d .
H017 H 0.478 -0.0543 0.0478 0.029 Uiso 1 calc R
C018 C 0.65451(15) -0.20273(17) 0.38314(7) 0.0261(4) Uani 1 d .
H018 H 0.6813 -0.2748 0.4097 0.031 Uiso 1 calc R
C019 C 0.32957(14) -0.10109(17) 0.15709(7) 0.0232(3) Uani 1 d .
H019 H 0.25 -0.1057 0.1674 0.028 Uiso 1 calc R
C020 C 0.42641(14) -0.12042(17) 0.19834(7) 0.0229(3) Uani 1 d .
H020 H 0.4128 -0.1373 0.2368 0.027 Uiso 1 calc R
C021 C 1.11027(16) -0.3921(2) 0.13234(8) 0.0318(4) Uani 1 d .
H02A H 1.1958 -0.404 0.1278 0.048 Uiso 1 calc R
H02B H 1.066 -0.361 0.096 0.048 Uiso 1 calc R
H02C H 1.0772 -0.4822 0.1437 0.048 Uiso 1 calc R
C022 C 0.24234(14) -0.04759(16) 0.05879(7) 0.0223(3) Uani 1 d .
C023 C 0.34618(14) -0.07476(16) 0.10010(7) 0.0219(3) Uani 1 d .
C024 C 0.15541(15) 0.02399(18) -0.02758(7) 0.0252(4) Uani 1 d .
C025 C 0.6183(2) -0.1629(2) 0.49785(8) 0.0400(5) Uani 1 d .
H02D H 0.6021 -0.1314 0.5358 0.06 Uiso 1 calc R
H02E H 0.7043 -0.185 0.4988 0.06 Uiso 1 calc R
H02F H 0.5703 -0.2474 0.4869 0.06 Uiso 1 calc R
C026 C 0.54494(14) -0.11563(17) 0.18455(7) 0.0222(3) Uani 1 d .
C027 C 0.91165(17) 0.2509(2) 0.13550(9) 0.0358(4) Uani 1 d .
H027 H 0.9432 0.2114 0.1713 0.043 Uiso 1 calc R
C028 C 0.12208(14) -0.05019(17) 0.06270(7) 0.0235(3) Uani 1 d .
H028 H 0.0854 -0.0761 0.0955 0.028 Uiso 1 calc R
C029 C 0.9433(2) 0.3334(2) 0.04272(10) 0.0463(5) Uani 1 d .
H029 H 0.9958 0.3512 0.0147 0.056 Uiso 1 calc R
C030 C 0.74584(19) 0.3385(2) 0.07206(9) 0.0408(5) Uani 1 d .
H030 H 0.6624 0.36 0.0637 0.049 Uiso 1 calc R
C031 C 0.8222(2) 0.3641(2) 0.03143(9) 0.0459(5) Uani 1 d .
H031 H 0.7912 0.4032 -0.0045 0.055 Uiso 1 calc R
C032 C 0.66591(15) -0.21949(18) 0.32524(7) 0.0264(4) Uani 1 d .
H032 H 0.6999 -0.304 0.3126 0.032 Uiso 1 calc R
C033 C 0.85853(15) -0.09491(18) 0.23052(7) 0.0254(4) Uani 1 d .
H033 H 0.85 -0.0099 0.2511 0.03 Uiso 1 calc R
C034 C 0.78910(17) 0.28179(19) 0.12504(8) 0.0353(4) Uani 1 d .
C035 C 0.98810(18) 0.2765(2) 0.09496(9) 0.0408(5) Uani 1 d .
H035 H 1.0716 0.2549 0.103 0.049 Uiso 1 calc R
C036 C 0.7073(2) 0.2555(2) 0.16968(10) 0.0490(5) Uani 1 d .
H03A H 0.6247 0.283 0.1548 0.073 Uiso 1 calc R
H03B H 0.7345 0.3114 0.2039 0.073 Uiso 1 calc R
H03C H 0.709 0.155 0.1796 0.073 Uiso 1 calc R
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
C007 O001 C025 117.05(13) .
C016 O002 C021 116.86(13) .
C022 O003 C024 107.30(12) .
C026 N005 C014 121.34(13) .
C026 N005 C013 121.12(13) .
C014 N005 C013 117.51(12) .
C009 C006 C013 120.43(15) .
C009 C006 H006 119.8 .
C013 C006 H006 119.8 .
O001 C007 C018 124.35(14) .
O001 C007 C009 115.82(14) .
C018 C007 C009 119.82(15) .
C014 C008 C010 120.62(15) .
C014 C008 H008 119.7 .
C010 C008 H008 119.7 .
C006 C009 C007 120.25(15) .
C006 C009 H009 119.9 .
C007 C009 H009 119.9 .
C016 C010 C008 119.25(16) .
C016 C010 H010 120.4 .
C008 C010 H010 120.4 .
C017 C011 C026 120.00(15) .
C017 C011 H011 120 .
C026 C011 H011 120 .
C033 C012 C016 120.07(15) .
C033 C012 H012 120 .
C016 C012 H012 120 .
C032 C013 C006 119.01(15) .
C032 C013 N005 120.25(14) .
C006 C013 N005 120.73(14) .
C008 C014 C033 119.66(15) .
C008 C014 N005 120.83(15) .
C033 C014 N005 119.50(15) .
C015 C015 C028 131.0(2) 3
C015 C015 C024 123.02(19) 3
C028 C015 C024 106.00(14) .
O002 C016 C010 124.22(15) .
O002 C016 C012 115.36(14) .
C010 C016 C012 120.41(15) .
C011 C017 C023 121.60(15) .
C011 C017 H017 119.2 .
C023 C017 H017 119.2 .
C007 C018 C032 119.37(15) .
C007 C018 H018 120.3 .
C032 C018 H018 120.3 .
C020 C019 C023 121.11(15) .
C020 C019 H019 119.4 .
C023 C019 H019 119.4 .
C019 C020 C026 121.01(15) .
C019 C020 H020 119.5 .
C026 C020 H020 119.5 .
O002 C021 H02A 109.5 .
O002 C021 H02B 109.5 .
H02A C021 H02B 109.5 .
O002 C021 H02C 109.5 .
H02A C021 H02C 109.5 .
H02B C021 H02C 109.5 .
C028 C022 O003 111.63(14) .
C028 C022 C023 132.14(15) .
O003 C022 C023 116.17(13) .
C019 C023 C017 117.80(14) .
C019 C023 C022 119.28(14) .
C017 C023 C022 122.88(14) .
O004 C024 O003 120.81(15) .
O004 C024 C015 132.10(16) .
O003 C024 C015 107.07(13) .
O001 C025 H02D 109.5 .
O001 C025 H02E 109.5 .
H02D C025 H02E 109.5 .
O001 C025 H02F 109.5 .
H02D C025 H02F 109.5 .
H02E C025 H02F 109.5 .
N005 C026 C020 120.31(14) .
N005 C026 C011 121.24(14) .
C020 C026 C011 118.45(14) .
C035 C027 C034 121.27(19) .
C035 C027 H027 119.4 .
C034 C027 H027 119.4 .
C022 C028 C015 107.97(15) .
C022 C028 H028 126 .
C015 C028 H028 126 .
C031 C029 C035 119.7(2) .
C031 C029 H029 120.2 .
C035 C029 H029 120.2 .
C031 C030 C034 120.97(19) .
C031 C030 H030 119.5 .
C034 C030 H030 119.5 .
C029 C031 C030 120.3(2) .
C029 C031 H031 119.8 .
C030 C031 H031 119.8 .
C013 C032 C018 121.11(15) .
C013 C032 H032 119.4 .
C018 C032 H032 119.4 .
C012 C033 C014 119.96(16) .
C012 C033 H033 120 .
C014 C033 H033 120 .
C030 C034 C027 117.82(19) .
C030 C034 C036 121.37(19) .
C027 C034 C036 120.81(19) .
C027 C035 C029 120.0(2) .
C027 C035 H035 120 .
C029 C035 H035 120 .
C034 C036 H03A 109.5 .
C034 C036 H03B 109.5 .
H03A C036 H03B 109.5 .
C034 C036 H03C 109.5 .
H03A C036 H03C 109.5 .
H03B C036 H03C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O001 C007 1.3700(19) .
O001 C025 1.431(2) .
O002 C016 1.3742(19) .
O002 C021 1.429(2) .
O003 C022 1.3960(19) .
O003 C024 1.3970(19) .
O004 C024 1.197(2) .
N005 C026 1.394(2) .
N005 C014 1.431(2) .
N005 C013 1.432(2) .
C006 C009 1.378(2) .
C006 C013 1.396(2) .
C006 H006 0.95 .
C007 C018 1.386(2) .
C007 C009 1.393(2) .
C008 C014 1.387(2) .
C008 C010 1.388(2) .
C008 H008 0.95 .
C009 H009 0.95 .
C010 C016 1.384(2) .
C010 H010 0.95 .
C011 C017 1.384(2) .
C011 C026 1.404(2) .
C011 H011 0.95 .
C012 C033 1.382(2) .
C012 C016 1.389(2) .
C012 H012 0.95 .
C013 C032 1.378(2) .
C014 C033 1.388(2) .
C015 C015 1.377(3) 3
C015 C028 1.420(2) .
C015 C024 1.476(2) .
C017 C023 1.401(2) .
C017 H017 0.95 .
C018 C032 1.394(2) .
C018 H018 0.95 .
C019 C020 1.375(2) .
C019 C023 1.400(2) .
C019 H019 0.95 .
C020 C026 1.401(2) .
C020 H020 0.95 .
C021 H02A 0.98 .
C021 H02B 0.98 .
C021 H02C 0.98 .
C022 C028 1.357(2) .
C022 C023 1.443(2) .
C025 H02D 0.98 .
C025 H02E 0.98 .
C025 H02F 0.98 .
C027 C035 1.378(3) .
C027 C034 1.391(3) .
C027 H027 0.95 .
C028 H028 0.95 .
C029 C031 1.377(3) .
C029 C035 1.380(3) .
C029 H029 0.95 .
C030 C031 1.379(3) .
C030 C034 1.390(3) .
C030 H030 0.95 .
C031 H031 0.95 .
C032 H032 0.95 .
C033 H033 0.95 .
C034 C036 1.496(3) .
C035 H035 0.95 .
C036 H03A 0.98 .
C036 H03B 0.98 .
C036 H03C 0.98 .
