#------------------------------------------------------------------------------
#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/36/4123606.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_4123606
loop_
_publ_author_name
'Tanioka, Masaru'
'Kamino, Shinichiro'
'Muranaka, Atsuya'
'Ooyama, Yousuke'
'Ota, Hiromi'
'Shirasaki, Yoshinao'
'Horigome, Jun'
'Ueda, Masashi'
'Uchiyama, Masanobu'
'Sawada, Daisuke'
'Enomoto, Shuichi'
_publ_section_title
;
 Reversible near-infrared/blue mechanofluorochromism of
 aminobenzopyranoxanthene.
;
_journal_issue                   20
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6436
_journal_page_last               6439
_journal_paper_doi               10.1021/jacs.5b00877
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C42 H36 N2 O6'
_chemical_formula_sum            'C42 H36 N2 O6'
_chemical_formula_weight         664.76
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_Hall           '-C 2ac 2'
_space_group_name_H-M_alt        'C m c e'
_symmetry_space_group_name_Hall  '-C 2ac 2'
_symmetry_space_group_name_H-M   'C m c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   26.038(6)
_cell_length_b                   17.781(4)
_cell_length_c                   15.709(3)
_cell_measurement_reflns_used    9066
_cell_measurement_temperature    110
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.00
_cell_volume                     7273(3)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            56964
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_min         3.063
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2800.00
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0662
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0939P)²+5.3956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1885
_refine_ls_wR_factor_ref         0.1925
_reflns_number_gt                4047
_reflns_number_total             4281
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja5b00877_si_007.cif
_cod_data_source_block           No121
_cod_depositor_comments
'Adding full bibliography for 4123606--4123614.cif.'
_cod_database_code               4123606
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,+Z
3 +X,1/2-Y,1/2+Z
4 -X,1/2-Y,1/2+Z
5 -X,-Y,-Z
6 +X,-Y,-Z
7 -X,1/2+Y,1/2-Z
8 +X,1/2+Y,1/2-Z
9 1/2+X,1/2+Y,+Z
10 1/2-X,1/2+Y,+Z
11 1/2+X,-Y,1/2+Z
12 1/2-X,-Y,1/2+Z
13 1/2-X,1/2-Y,-Z
14 1/2+X,1/2-Y,-Z
15 1/2-X,+Y,1/2-Z
16 1/2+X,+Y,1/2-Z
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_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.58912(5) 0.45221(7) 0.90961(8) 0.0245(3) Uani 1 16 d .
O2 O 0.59837(5) 0.67184(7) 0.90970(8) 0.0240(3) Uani 1 16 d .
O3 O 0.59849(7) 0.79761(8) 0.90734(9) 0.0379(4) Uani 1 16 d .
N1 N 0.76931(6) 0.42060(9) 0.92252(10) 0.0281(4) Uani 1 16 d .
C1 C 0.64174(7) 0.55783(10) 0.86366(11) 0.0213(4) Uani 1 16 d .
C2 C 0.69194(7) 0.58259(10) 0.85099(11) 0.0244(4) Uani 1 16 d .
C3 C 0.73415(7) 0.53856(11) 0.86854(11) 0.0255(4) Uani 1 16 d .
C4 C 0.72786(7) 0.46495(11) 0.90159(11) 0.0240(4) Uani 1 16 d .
C5 C 0.67772(7) 0.43918(10) 0.91323(11) 0.0238(4) Uani 1 16 d .
C6 C 0.63635(7) 0.48522(10) 0.89506(11) 0.0214(4) Uani 1 16 d .
C7 C 0.54581(7) 0.49234(10) 0.89180(11) 0.0223(4) Uani 1 16 d .
C8 C 0.5 0.45521(14) 0.90617(16) 0.0228(5) Uani 1 8 d .
C9 C 0.5 0.60112(14) 0.84677(16) 0.0222(5) Uani 1 8 d .
C10 C 0.54687(7) 0.56626(10) 0.86167(11) 0.0218(4) Uani 1 16 d .
C11 C 0.59655(7) 0.60765(10) 0.84710(11) 0.0218(4) Uani 1 16 d .
C12 C 0.59724(7) 0.64902(10) 0.76290(11) 0.0227(4) Uani 1 16 d .
C13 C 0.59598(7) 0.62013(11) 0.68116(12) 0.0290(4) Uani 1 16 d .
C14 C 0.59443(8) 0.67051(12) 0.61375(13) 0.0316(5) Uani 1 16 d .
C15 C 0.59304(8) 0.74793(12) 0.62726(14) 0.0338(5) Uani 1 16 d .
C16 C 0.59383(8) 0.77637(11) 0.70946(14) 0.0317(5) Uani 1 16 d .
C17 C 0.59641(7) 0.72513(10) 0.77601(12) 0.0246(4) Uani 1 16 d .
C18 C 0.59777(7) 0.73901(11) 0.86883(12) 0.0262(4) Uani 1 16 d .
C19 C 0.82167(8) 0.44444(12) 0.90332(12) 0.0300(4) Uani 1 16 d .
C20 C 0.83601(9) 0.43306(12) 0.81094(13) 0.0349(5) Uani 1 16 d .
C21 C 0.76153(8) 0.34198(11) 0.94503(13) 0.0323(5) Uani 1 16 d .
C22 C 0.74757(9) 0.29098(12) 0.87070(14) 0.0377(5) Uani 1 16 d .
H2 H 0.69727 0.63187 0.82935 0.0293 Uiso 1 16 calc R
H3 H 0.76768 0.55764 0.85844 0.0305 Uiso 1 16 calc R
H5 H 0.67197 0.38965 0.93378 0.0286 Uiso 1 16 calc R
H8 H 0.5 0.40466 0.92574 0.0274 Uiso 1 8 calc R
H9 H 0.5 0.6511 0.8254 0.0266 Uiso 1 8 calc R
H13 H 0.59618 0.56739 0.67147 0.0348 Uiso 1 16 calc R
H14 H 0.59431 0.65179 0.55711 0.0379 Uiso 1 16 calc R
H15 H 0.59154 0.78129 0.58008 0.0405 Uiso 1 16 calc R
H16 H 0.59265 0.82898 0.71985 0.0381 Uiso 1 16 calc R
H19A H 0.84584 0.41573 0.93953 0.0360 Uiso 1 16 calc R
H19B H 0.8254 0.49836 0.91777 0.0360 Uiso 1 16 calc R
H20A H 0.8714 0.44994 0.80169 0.0419 Uiso 1 16 calc R
H20B H 0.83319 0.3796 0.79651 0.0419 Uiso 1 16 calc R
H20C H 0.81273 0.46226 0.77474 0.0419 Uiso 1 16 calc R
H21A H 0.73385 0.33901 0.98811 0.0388 Uiso 1 16 calc R
H21B H 0.79336 0.32271 0.97172 0.0388 Uiso 1 16 calc R
H22A H 0.74304 0.23938 0.89128 0.0453 Uiso 1 16 calc R
H22B H 0.71552 0.30854 0.84469 0.0453 Uiso 1 16 calc R
H22C H 0.77515 0.29221 0.82827 0.0453 Uiso 1 16 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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(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_publ_flag
_geom_angle_site_symmetry_3
C6 O1 C7 118.68(14) yes .
C11 O2 C18 110.96(13) yes .
C4 N1 C19 121.11(16) yes .
C4 N1 C21 119.93(16) yes .
C19 N1 C21 117.33(16) yes .
C2 C1 C6 116.05(16) yes .
C2 C1 C11 121.73(16) yes .
C6 C1 C11 122.19(16) yes .
C1 C2 C3 122.71(17) yes .
C2 C3 C4 120.40(17) yes .
N1 C4 C3 121.73(17) yes .
N1 C4 C5 120.93(17) yes .
C3 C4 C5 117.34(17) yes .
C4 C5 C6 120.48(17) yes .
O1 C6 C1 122.92(16) yes .
O1 C6 C5 114.06(15) yes .
C1 C6 C5 123.01(17) yes .
O1 C7 C8 115.49(16) yes .
O1 C7 C10 123.05(16) yes .
C8 C7 C10 121.45(17) yes .
C7 C8 C7 119.3(2) yes 2_655
C10 C9 C10 123.0(2) yes 2_655
C7 C10 C9 117.36(17) yes .
C7 C10 C11 121.89(16) yes .
C9 C10 C11 120.74(17) yes .
O2 C11 C1 108.08(14) yes .
O2 C11 C10 107.33(14) yes .
O2 C11 C12 101.64(13) yes .
C1 C11 C10 111.10(15) yes .
C1 C11 C12 115.50(15) yes .
C10 C11 C12 112.37(15) yes .
C11 C12 C13 129.08(17) yes .
C11 C12 C17 110.41(15) yes .
C13 C12 C17 120.42(17) yes .
C12 C13 C14 117.99(18) yes .
C13 C14 C15 121.49(19) yes .
C14 C15 C16 120.11(19) yes .
C15 C16 C17 117.55(18) yes .
C12 C17 C16 122.42(18) yes .
C12 C17 C18 108.23(16) yes .
C16 C17 C18 129.34(17) yes .
O2 C18 O3 121.58(17) yes .
O2 C18 C17 108.66(15) yes .
O3 C18 C17 129.75(18) yes .
N1 C19 C20 112.97(17) yes .
N1 C21 C22 114.76(17) yes .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
O1 C6 1.382(2) yes .
O1 C7 1.364(2) yes .
O2 C11 1.507(2) yes .
O2 C18 1.356(2) yes .
O3 C18 1.205(2) yes .
N1 C4 1.377(2) yes .
N1 C19 1.459(3) yes .
N1 C21 1.456(3) yes .
C1 C2 1.394(3) yes .
C1 C6 1.389(3) yes .
C1 C11 1.496(3) yes .
C2 C3 1.377(3) yes .
C3 C4 1.418(3) yes .
C4 C5 1.396(3) yes .
C5 C6 1.383(3) yes .
C7 C8 1.382(2) yes .
C7 C10 1.397(3) yes .
C9 C10 1.389(2) yes .
C9 C10 1.389(2) yes 2_655
C10 C11 1.506(3) yes .
C11 C12 1.514(2) yes .
C12 C13 1.383(3) yes .
C12 C17 1.369(3) yes .
C13 C14 1.388(3) yes .
C14 C15 1.393(3) yes .
C15 C16 1.387(3) yes .
C16 C17 1.388(3) yes .
C17 C18 1.479(3) yes .
C19 C20 1.512(3) yes .
C21 C22 1.522(3) yes .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.000 242 26 ' '
2 0.000 0.500 0.000 242 26 ' '
3 0.000 0.000 0.500 241 26 ' '
4 0.500 0.500 0.500 241 26 ' '
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 122368909
