#------------------------------------------------------------------------------
#$Date: 2015-06-05 07:12:11 +0300 (Fri, 05 Jun 2015) $
#$Revision: 138216 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/36/4123614.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_4123614
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         'C43 H38 Cl2 N2 O6'
_chemical_formula_sum            'C43 H38 Cl2 N2 O6'
_chemical_formula_weight         749.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 112.188(4)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   15.709(4)
_cell_length_b                   15.886(4)
_cell_length_c                   15.961(4)
_cell_measurement_reflns_used    10685
_cell_measurement_temperature    273
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.04
_cell_volume                     3688.2(16)
_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    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273
_diffrn_detector_area_resol_mean 29.257
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_laue_measured_fraction_full 0.997
_diffrn_reflns_laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            58325
_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         27.493
_diffrn_reflns_theta_min         3.040
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1568.00
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     478
_refine_ls_number_reflns         8441
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0558P)²+0.9898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                7329
_reflns_number_total             8441
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja5b00877_si_002.cif
_cod_data_source_block           No106_CH2Cl2_EtOAc
_cod_depositor_comments
'Adding full bibliography for 4123606--4123614.cif.'
_cod_original_cell_volume        3688.1(16)
_cod_database_code               4123614
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-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
Cl91 Cl 0.45552(3) 0.97128(3) 0.58454(3) 0.03086(11) Uani 1 4 d .
Cl92 Cl 0.53689(4) 0.81225(3) 0.56197(5) 0.05320(17) Uani 1 4 d .
O1 O 0.44332(7) 0.59401(7) 0.64973(7) 0.0191(2) Uani 1 4 d .
O2 O 0.20985(7) 0.58948(6) 0.44343(7) 0.0174(2) Uani 1 4 d .
O3 O 0.08349(7) 0.58623(7) 0.31645(7) 0.0248(2) Uani 1 4 d .
O11 O 0.61760(7) 0.58913(7) 0.47104(7) 0.0191(2) Uani 1 4 d .
O12 O 0.40147(7) 0.58590(6) 0.24430(7) 0.0180(2) Uani 1 4 d .
O13 O 0.27013(8) 0.58600(7) 0.12140(8) 0.0276(3) Uani 1 4 d .
N1 N 0.29834(9) 0.58214(8) 0.86098(9) 0.0222(3) Uani 1 4 d .
N11 N 0.82942(9) 0.57712(8) 0.32615(9) 0.0213(3) Uani 1 4 d .
C1 C 0.28401(10) 0.64036(9) 0.59724(10) 0.0166(3) Uani 1 4 d .
C2 C 0.20928(10) 0.65430(9) 0.62309(10) 0.0191(3) Uani 1 4 d .
C3 C 0.21299(11) 0.63712(10) 0.70893(10) 0.0204(3) Uani 1 4 d .
C4 C 0.29410(11) 0.60392(9) 0.77589(10) 0.0190(3) Uani 1 4 d .
C5 C 0.37000(11) 0.59237(9) 0.75120(10) 0.0187(3) Uani 1 4 d .
C6 C 0.36335(10) 0.60983(9) 0.66422(10) 0.0167(3) Uani 1 4 d .
C7 C 0.44399(10) 0.60935(9) 0.56552(10) 0.0165(3) Uani 1 4 d .
C8 C 0.52709(10) 0.59398(9) 0.55687(10) 0.0174(3) Uani 1 4 d .
C9 C 0.37775(10) 0.65171(9) 0.41125(10) 0.0168(3) Uani 1 4 d .
C10 C 0.36753(10) 0.63807(9) 0.49306(10) 0.0158(3) Uani 1 4 d .
C11 C 0.27676(10) 0.65337(9) 0.50191(10) 0.0159(3) Uani 1 4 d .
C12 C 0.23333(10) 0.73520(9) 0.45720(10) 0.0161(3) Uani 1 4 d .
C13 C 0.26475(11) 0.81693(9) 0.47988(10) 0.0207(3) Uani 1 4 d .
C14 C 0.21702(11) 0.88128(10) 0.42227(11) 0.0241(3) Uani 1 4 d .
C15 C 0.14025(11) 0.86476(10) 0.34388(11) 0.0250(3) Uani 1 4 d .
C16 C 0.10909(11) 0.78312(10) 0.32152(11) 0.0233(3) Uani 1 4 d .
C17 C 0.15710(10) 0.71898(9) 0.38014(10) 0.0174(3) Uani 1 4 d .
C18 C 0.14263(10) 0.62686(9) 0.37280(10) 0.0176(3) Uani 1 4 d .
C19 C 0.22237(12) 0.59989(10) 0.88957(11) 0.0244(3) Uani 1 4 d .
C20 C 0.21711(12) 0.69108(11) 0.91552(12) 0.0294(4) Uani 1 4 d .
C21 C 0.38604(12) 0.55840(11) 0.93118(11) 0.0273(4) Uani 1 4 d .
C22 C 0.45210(13) 0.63137(12) 0.97028(12) 0.0344(4) Uani 1 4 d .
C31 C 0.56126(10) 0.63169(9) 0.31271(10) 0.0168(3) Uani 1 4 d .
C32 C 0.58637(10) 0.64403(9) 0.23823(10) 0.0191(3) Uani 1 4 d .
C33 C 0.67344(10) 0.62755(9) 0.24122(11) 0.0201(3) Uani 1 4 d .
C34 C 0.74254(10) 0.59644(9) 0.32146(11) 0.0184(3) Uani 1 4 d .
C35 C 0.71836(10) 0.58508(9) 0.39672(10) 0.0181(3) Uani 1 4 d .
C36 C 0.63025(10) 0.60237(9) 0.39090(10) 0.0168(3) Uani 1 4 d .
C37 C 0.53368(10) 0.60731(9) 0.47389(10) 0.0166(3) Uani 1 4 d .
C40 C 0.45925(10) 0.63632(9) 0.39912(10) 0.0161(3) Uani 1 4 d .
C41 C 0.46570(10) 0.64853(9) 0.30785(10) 0.0160(3) Uani 1 4 d .
C42 C 0.42425(10) 0.73132(9) 0.26382(10) 0.0162(3) Uani 1 4 d .
C43 C 0.45452(11) 0.81309(10) 0.28887(11) 0.0223(3) Uani 1 4 d .
C44 C 0.40247(12) 0.87855(10) 0.23746(11) 0.0264(4) Uani 1 4 d .
C45 C 0.32023(12) 0.86388(10) 0.16391(11) 0.0274(4) Uani 1 4 d .
C46 C 0.28961(11) 0.78238(10) 0.13961(10) 0.0243(3) Uani 1 4 d .
C47 C 0.34378(10) 0.71688(9) 0.19008(10) 0.0182(3) Uani 1 4 d .
C48 C 0.33057(10) 0.62501(9) 0.17821(10) 0.0187(3) Uani 1 4 d .
C49 C 0.85643(11) 0.59091(10) 0.24964(11) 0.0225(3) Uani 1 4 d .
C50 C 0.88285(12) 0.68163(10) 0.24078(12) 0.0261(3) Uani 1 4 d .
C51 C 0.90153(11) 0.55488(10) 0.41256(11) 0.0240(3) Uani 1 4 d .
C52 C 0.93902(12) 0.62889(11) 0.47691(12) 0.0301(4) Uani 1 4 d .
C91 C 0.55875(12) 0.91351(11) 0.60934(12) 0.0288(4) Uani 1 4 d .
H2 H 0.15516 0.67596 0.58068 0.0229 Uiso 1 4 calc R
H3 H 0.16176 0.64738 0.72323 0.0245 Uiso 1 4 calc R
H5 H 0.42521 0.5728 0.79372 0.0225 Uiso 1 4 calc R
H8 H 0.57758 0.57503 0.60601 0.0209 Uiso 1 4 calc R
H9 H 0.32772 0.67205 0.36255 0.0202 Uiso 1 4 calc R
H13 H 0.31603 0.82827 0.53187 0.0248 Uiso 1 4 calc R
H14 H 0.23666 0.93658 0.43627 0.0289 Uiso 1 4 calc R
H15 H 0.10977 0.90898 0.30635 0.0299 Uiso 1 4 calc R
H16 H 0.0581 0.77144 0.2694 0.0279 Uiso 1 4 calc R
H19A H 0.22846 0.56442 0.94099 0.0293 Uiso 1 4 calc R
H19B H 0.16516 0.58505 0.84079 0.0293 Uiso 1 4 calc R
H20A H 0.16576 0.69823 0.93355 0.0352 Uiso 1 4 calc R
H20B H 0.2728 0.70602 0.96487 0.0352 Uiso 1 4 calc R
H20C H 0.20944 0.72667 0.86457 0.0352 Uiso 1 4 calc R
H21A H 0.41578 0.5175 0.90616 0.0328 Uiso 1 4 calc R
H21B H 0.37407 0.53117 0.98002 0.0328 Uiso 1 4 calc R
H22A H 0.5078 0.61058 1.01574 0.0412 Uiso 1 4 calc R
H22B H 0.46595 0.65791 0.92289 0.0412 Uiso 1 4 calc R
H22C H 0.42417 0.6716 0.99687 0.0412 Uiso 1 4 calc R
H32 H 0.54243 0.66418 0.18462 0.0229 Uiso 1 4 calc R
H33 H 0.68713 0.63689 0.19016 0.0241 Uiso 1 4 calc R
H35 H 0.76201 0.56576 0.45093 0.0217 Uiso 1 4 calc R
H43 H 0.50818 0.82356 0.33873 0.0268 Uiso 1 4 calc R
H44 H 0.42268 0.93362 0.25219 0.0316 Uiso 1 4 calc R
H45 H 0.28597 0.90905 0.13119 0.0328 Uiso 1 4 calc R
H46 H 0.23475 0.77176 0.09123 0.0292 Uiso 1 4 calc R
H49A H 0.80593 0.57483 0.19455 0.0270 Uiso 1 4 calc R
H49B H 0.90822 0.55471 0.25591 0.0270 Uiso 1 4 calc R
H50A H 0.89994 0.68669 0.18925 0.0313 Uiso 1 4 calc R
H50B H 0.83146 0.71779 0.23304 0.0313 Uiso 1 4 calc R
H50C H 0.93381 0.69766 0.29444 0.0313 Uiso 1 4 calc R
H51A H 0.95192 0.52904 0.40092 0.0288 Uiso 1 4 calc R
H51B H 0.87742 0.51323 0.44223 0.0288 Uiso 1 4 calc R
H52A H 0.98589 0.60928 0.53191 0.0362 Uiso 1 4 calc R
H52B H 0.96468 0.6699 0.44897 0.0362 Uiso 1 4 calc R
H52C H 0.89007 0.65407 0.49035 0.0362 Uiso 1 4 calc R
H91A H 0.59872 0.94341 0.58571 0.0345 Uiso 1 4 calc R
H91B H 0.59029 0.909 0.67443 0.0345 Uiso 1 4 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)
;
Cl Cl 0.1484 0.1585
;
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
C6 O1 C7 118.40(11) yes
C11 O2 C18 111.25(10) yes
C36 O11 C37 118.42(11) yes
C41 O12 C48 111.40(10) yes
C4 N1 C19 121.29(12) yes
C4 N1 C21 120.11(16) yes
C19 N1 C21 117.19(14) yes
C34 N11 C49 121.35(12) yes
C34 N11 C51 120.42(16) yes
C49 N11 C51 117.51(14) yes
C2 C1 C6 115.92(15) yes
C2 C1 C11 121.80(12) yes
C6 C1 C11 122.20(16) yes
C1 C2 C3 122.45(13) yes
C2 C3 C4 120.77(17) yes
N1 C4 C3 122.05(17) yes
N1 C4 C5 120.95(13) yes
C3 C4 C5 116.99(15) yes
C4 C5 C6 120.46(13) yes
O1 C6 C1 122.88(15) yes
O1 C6 C5 113.76(12) yes
C1 C6 C5 123.36(17) yes
O1 C7 C8 115.03(12) yes
O1 C7 C10 123.32(16) yes
C8 C7 C10 121.65(16) yes
C7 C8 C37 118.85(12) yes
C10 C9 C40 122.91(12) yes
C7 C10 C9 117.48(16) yes
C7 C10 C11 121.71(15) yes
C9 C10 C11 120.81(12) yes
O2 C11 C1 107.73(13) yes
O2 C11 C10 107.30(12) yes
O2 C11 C12 101.63(10) yes
C1 C11 C10 111.23(11) yes
C1 C11 C12 116.43(14) yes
C10 C11 C12 111.62(14) yes
C11 C12 C13 128.85(12) yes
C11 C12 C17 110.16(12) yes
C13 C12 C17 120.74(13) yes
C12 C13 C14 117.76(12) yes
C13 C14 C15 121.48(14) yes
C14 C15 C16 120.58(14) yes
C15 C16 C17 117.51(13) yes
C12 C17 C16 121.93(13) yes
C12 C17 C18 108.14(12) yes
C16 C17 C18 129.88(12) yes
O2 C18 O3 121.58(13) yes
O2 C18 C17 108.62(11) yes
O3 C18 C17 129.80(12) yes
N1 C19 C20 113.93(15) yes
N1 C21 C22 114.67(14) yes
C32 C31 C36 115.82(15) yes
C32 C31 C41 121.95(12) yes
C36 C31 C41 122.24(16) yes
C31 C32 C33 122.62(13) yes
C32 C33 C34 120.62(17) yes
N11 C34 C33 122.21(17) yes
N11 C34 C35 120.66(13) yes
C33 C34 C35 117.12(15) yes
C34 C35 C36 120.43(13) yes
O11 C36 C31 123.13(15) yes
O11 C36 C35 113.49(12) yes
C31 C36 C35 123.38(16) yes
O11 C37 C8 114.92(12) yes
O11 C37 C40 123.23(16) yes
C8 C37 C40 121.84(16) yes
C9 C40 C37 117.26(16) yes
C9 C40 C41 120.91(12) yes
C37 C40 C41 121.81(15) yes
O12 C41 C31 108.70(12) yes
O12 C41 C40 107.04(12) yes
O12 C41 C42 101.52(10) yes
C31 C41 C40 110.98(11) yes
C31 C41 C42 115.17(14) yes
C40 C41 C42 112.62(14) yes
C41 C42 C43 129.56(12) yes
C41 C42 C47 110.18(12) yes
C43 C42 C47 120.24(13) yes
C42 C43 C44 118.06(13) yes
C43 C44 C45 121.60(14) yes
C44 C45 C46 120.27(14) yes
C45 C46 C47 117.71(13) yes
C42 C47 C46 122.08(13) yes
C42 C47 C48 108.20(12) yes
C46 C47 C48 129.73(12) yes
O12 C48 O13 121.95(13) yes
O12 C48 C47 108.52(11) yes
O13 C48 C47 129.53(12) yes
N11 C49 C50 113.43(15) yes
N11 C51 C52 114.47(13) yes
Cl91 C91 Cl92 111.38(9) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl91 C91 1.7731(19) yes
Cl92 C91 1.7553(19) yes
O1 C6 1.384(2) yes
O1 C7 1.370(2) yes
O2 C11 1.5050(16) yes
O2 C18 1.3562(16) yes
O3 C18 1.2073(16) yes
O11 C36 1.383(2) yes
O11 C37 1.367(2) yes
O12 C41 1.5046(16) yes
O12 C48 1.3608(16) yes
O13 C48 1.2072(17) yes
N1 C4 1.378(2) yes
N1 C19 1.457(3) yes
N1 C21 1.4594(19) yes
N11 C34 1.373(2) yes
N11 C49 1.453(3) yes
N11 C51 1.4595(18) yes
C1 C2 1.401(3) yes
C1 C6 1.3875(18) yes
C1 C11 1.497(2) yes
C2 C3 1.376(2) yes
C3 C4 1.420(2) yes
C4 C5 1.402(3) yes
C5 C6 1.380(2) yes
C7 C8 1.385(2) yes
C7 C10 1.3925(18) yes
C8 C37 1.383(2) yes
C9 C10 1.391(2) yes
C9 C40 1.387(2) yes
C10 C11 1.505(2) yes
C11 C12 1.516(2) yes
C12 C13 1.388(2) yes
C12 C17 1.3787(18) yes
C13 C14 1.390(2) yes
C14 C15 1.396(2) yes
C15 C16 1.385(2) yes
C16 C17 1.396(2) yes
C17 C18 1.479(2) yes
C19 C20 1.517(2) yes
C21 C22 1.523(2) yes
C31 C32 1.400(3) yes
C31 C36 1.3883(18) yes
C31 C41 1.498(2) yes
C32 C33 1.376(2) yes
C33 C34 1.4187(19) yes
C34 C35 1.402(3) yes
C35 C36 1.379(2) yes
C37 C40 1.3963(18) yes
C40 C41 1.510(2) yes
C41 C42 1.517(2) yes
C42 C43 1.389(2) yes
C42 C47 1.3828(18) yes
C43 C44 1.384(2) yes
C44 C45 1.399(2) yes
C45 C46 1.385(2) yes
C46 C47 1.392(2) yes
C47 C48 1.476(2) yes
C49 C50 1.521(2) yes
C51 C52 1.526(2) yes
