#------------------------------------------------------------------------------
#$Date: 2019-11-24 17:03:57 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238709 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/78/7237889.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_7237889
loop_
_publ_author_name
'Yano, Yoshio'
'Ono, Toshikazu'
'Hatanaka, Sou'
'Gryko, Daniel T.'
'Hisaeda, Yoshio'
_publ_section_title
;
 Salt--cocrystal continuum for photofunction modulation:
 stimuli-responsive fluorescence color-tuning of pyridine-modified
 intramolecular charge-transfer dyes and acid complexes
;
_journal_issue                   29
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              8847
_journal_paper_doi               10.1039/C9TC02524C
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         'C30 H24 N4, 2(C7 H6 O3)'
_chemical_formula_sum            'C44 H36 N4 O6'
_chemical_formula_weight         716.77
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-20
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha                112.739(6)
_cell_angle_beta                 101.751(5)
_cell_angle_gamma                102.668(4)
_cell_formula_units_Z            1
_cell_length_a                   6.5494(3)
_cell_length_b                   12.4521(7)
_cell_length_c                   12.9443(8)
_cell_measurement_reflns_used    2690
_cell_measurement_temperature    123
_cell_measurement_theta_max      33.1660
_cell_measurement_theta_min      3.0430
_cell_volume                     899.79(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   45.23    --   30.00  54.00 -90.00  193
  2  ω    -74.00 -35.00   1.00   45.23    --   30.00  54.00   0.00   39
  3  ω     36.00 109.00   1.00   45.23    --   30.00  54.00   0.00   73
  4  ω    -70.00 114.00   1.00   45.23    --   30.00  54.00 150.00  184
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0300639000
_diffrn_orient_matrix_UB_12      -0.0275848000
_diffrn_orient_matrix_UB_13      -0.0625733000
_diffrn_orient_matrix_UB_21      0.0196994000
_diffrn_orient_matrix_UB_22      0.0591346000
_diffrn_orient_matrix_UB_23      0.0018185000
_diffrn_orient_matrix_UB_31      0.1115357000
_diffrn_orient_matrix_UB_32      0.0048089000
_diffrn_orient_matrix_UB_33      0.0039353000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7850
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.136
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0590P)²+0.3020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1186
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2977
_reflns_number_total             3668
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9tc02524c14.cif
_cod_data_source_block           yano047
_cod_original_cell_volume        899.78(10)
_cod_database_code               7237889
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C44 H36 N4 O6 '
_chemical_oxdiff_usercomment     'yo-20-Salicylic acid'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_diffrn_oxdiff_ac3_digest_frames
;
0189bba689e80defb3ec6878d4bbbe280200489f651
;
_diffrn_oxdiff_ac3_digest_hkl
;
01525ebf5b74b825e9baec2a6d88bce22c4c32
;
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C3A(H3Aa), C4A(H4A), C5A(H5A), C6A(H6A)
2.b Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
2.c Idealised tetrahedral OH refined as rotating group:
 O3A(H3A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.095
_oxdiff_exptl_absorpt_empirical_full_min 0.908
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
N1 N 0.48012(19) 0.13174(10) 0.10441(10) 0.0195(3) Uani 1 1 d .
N2 N 0.1951(2) 0.41695(11) 0.09341(11) 0.0228(3) Uani 1 1 d .
C1 C 0.5610(2) 0.03543(12) 0.05915(13) 0.0194(3) Uani 1 1 d .
C2 C 0.3061(2) 0.11763(13) 0.01143(13) 0.0200(3) Uani 1 1 d .
C3 C 0.2784(2) 0.01563(12) -0.09038(13) 0.0202(3) Uani 1 1 d .
H3 H 0.175422 -0.013614 -0.164386 0.024 Uiso 1 1 calc R
C4 C 0.1878(2) 0.20705(13) 0.02416(13) 0.0194(3) Uani 1 1 d .
C5 C 0.2991(2) 0.33406(13) 0.08228(13) 0.0217(3) Uani 1 1 d .
H5 H 0.452204 0.362116 0.114602 0.026 Uiso 1 1 calc R
C6 C -0.0262(2) 0.37736(14) 0.04722(14) 0.0241(3) Uani 1 1 d .
H6 H -0.098848 0.435162 0.056950 0.029 Uiso 1 1 calc R
C7 C -0.1489(2) 0.25334(13) -0.01429(13) 0.0234(3) Uani 1 1 d .
H7 H -0.301589 0.227983 -0.047072 0.028 Uiso 1 1 calc R
C8 C -0.0410(2) 0.16750(13) -0.02631(13) 0.0212(3) Uani 1 1 d .
H8 H -0.120822 0.083646 -0.067963 0.025 Uiso 1 1 calc R
C9 C 0.5407(2) 0.21162(12) 0.22756(13) 0.0199(3) Uani 1 1 d .
C10 C 0.7633(2) 0.27217(13) 0.29301(13) 0.0227(3) Uani 1 1 d .
H10 H 0.870155 0.265909 0.255493 0.027 Uiso 1 1 calc R
C11 C 0.8251(3) 0.34187(13) 0.41437(14) 0.0266(3) Uani 1 1 d .
H11 H 0.974446 0.380632 0.457695 0.032 Uiso 1 1 calc R
C12 C 0.6703(3) 0.35545(13) 0.47308(14) 0.0285(4) Uani 1 1 d .
C13 C 0.4480(3) 0.29714(14) 0.40508(14) 0.0296(4) Uani 1 1 d .
H13 H 0.340754 0.307083 0.441937 0.035 Uiso 1 1 calc R
C14 C 0.3825(2) 0.22459(13) 0.28367(14) 0.0250(3) Uani 1 1 d .
H14 H 0.233302 0.184934 0.240293 0.030 Uiso 1 1 calc R
C15 C 0.7382(3) 0.42703(16) 0.60562(15) 0.0414(4) Uani 1 1 d .
H15A H 0.698792 0.371505 0.638592 0.062 Uiso 1 1 calc GR
H15B H 0.663998 0.486970 0.625877 0.062 Uiso 1 1 calc GR
H15C H 0.895071 0.468250 0.636864 0.062 Uiso 1 1 calc GR
O1A O 0.72658(18) 0.60975(10) 0.19214(11) 0.0367(3) Uani 1 1 d .
O2A O 0.40893(17) 0.64949(9) 0.18558(10) 0.0269(3) Uani 1 1 d .
H2A H 0.332(4) 0.553(2) 0.147(2) 0.073(7) Uiso 1 1 d .
O3A O 1.09252(18) 0.79418(11) 0.28473(12) 0.0361(3) Uani 1 1 d .
H3A H 1.013543 0.721632 0.251076 0.054 Uiso 1 1 calc GR
C1A C 0.7364(2) 0.81893(13) 0.28017(13) 0.0215(3) Uani 1 1 d .
C2A C 0.9672(2) 0.86694(14) 0.31072(14) 0.0246(3) Uani 1 1 d .
C3A C 1.0728(2) 0.99452(15) 0.37142(14) 0.0278(4) Uani 1 1 d .
H3AA H 1.224798 1.027096 0.389345 0.033 Uiso 1 1 calc R
C4A C 0.9525(2) 1.07180(14) 0.40460(14) 0.0263(3) Uani 1 1 d .
H4A H 1.024691 1.156516 0.446515 0.032 Uiso 1 1 calc R
C5A C 0.7240(3) 1.02551(14) 0.37655(14) 0.0262(3) Uani 1 1 d .
H5A H 0.644097 1.078739 0.399620 0.031 Uiso 1 1 calc R
C6A C 0.6176(2) 0.89972(13) 0.31415(13) 0.0231(3) Uani 1 1 d .
H6A H 0.464975 0.868363 0.294476 0.028 Uiso 1 1 calc R
C7A C 0.6240(2) 0.68347(13) 0.21548(13) 0.0232(3) Uani 1 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 0.0000 0.0000 '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 0.0060 '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
C1 N1 C2 107.06(11) . .
C1 N1 C9 123.39(11) . .
C2 N1 C9 128.47(12) . .
C5 N2 C6 119.08(12) . .
N1 C1 C3 142.75(13) . 2_655
C1 C1 N1 107.73(15) 2_655 .
C1 C1 C3 109.51(15) 2_655 2_655
N1 C2 C4 122.77(12) . .
C3 C2 N1 110.04(12) . .
C3 C2 C4 127.04(13) . .
C1 C3 H3 127.2 2_655 .
C2 C3 C1 105.65(12) . 2_655
C2 C3 H3 127.2 . .
C5 C4 C2 121.78(12) . .
C8 C4 C2 120.77(12) . .
C8 C4 C5 117.39(13) . .
N2 C5 C4 122.79(13) . .
N2 C5 H5 118.6 . .
C4 C5 H5 118.6 . .
N2 C6 H6 119.0 . .
N2 C6 C7 121.95(13) . .
C7 C6 H6 119.0 . .
C6 C7 H7 120.5 . .
C6 C7 C8 118.93(13) . .
C8 C7 H7 120.5 . .
C4 C8 H8 120.1 . .
C7 C8 C4 119.81(13) . .
C7 C8 H8 120.1 . .
C10 C9 N1 119.10(13) . .
C14 C9 N1 121.06(13) . .
C14 C9 C10 119.75(14) . .
C9 C10 H10 120.2 . .
C11 C10 C9 119.66(14) . .
C11 C10 H10 120.2 . .
C10 C11 H11 119.1 . .
C10 C11 C12 121.82(14) . .
C12 C11 H11 119.1 . .
C11 C12 C13 117.46(14) . .
C11 C12 C15 121.67(15) . .
C13 C12 C15 120.84(16) . .
C12 C13 H13 119.2 . .
C14 C13 C12 121.64(15) . .
C14 C13 H13 119.2 . .
C9 C14 C13 119.62(14) . .
C9 C14 H14 120.2 . .
C13 C14 H14 120.2 . .
C12 C15 H15A 109.5 . .
C12 C15 H15B 109.5 . .
C12 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C7A O2A H2A 113.5(13) . .
C2A O3A H3A 109.5 . .
C2A C1A C7A 119.54(13) . .
C6A C1A C2A 119.28(13) . .
C6A C1A C7A 121.15(13) . .
O3A C2A C1A 122.36(14) . .
O3A C2A C3A 118.16(13) . .
C3A C2A C1A 119.48(14) . .
C2A C3A H3AA 120.0 . .
C4A C3A C2A 120.04(14) . .
C4A C3A H3AA 120.0 . .
C3A C4A H4A 119.4 . .
C3A C4A C5A 121.12(14) . .
C5A C4A H4A 119.4 . .
C4A C5A H5A 120.4 . .
C6A C5A C4A 119.21(14) . .
C6A C5A H5A 120.4 . .
C1A C6A H6A 119.6 . .
C5A C6A C1A 120.82(13) . .
C5A C6A H6A 119.6 . .
O1A C7A O2A 123.23(14) . .
O1A C7A C1A 122.42(13) . .
O2A C7A C1A 114.35(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3873(18) .
N1 C2 1.4028(18) .
N1 C9 1.4252(18) .
N2 C5 1.3356(18) .
N2 C6 1.3441(19) .
C1 C1 1.382(3) 2_655
C1 C3 1.4112(19) 2_655
C2 C3 1.375(2) .
C2 C4 1.4686(19) .
C3 H3 0.9300 .
C4 C5 1.3963(19) .
C4 C8 1.3938(19) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C6 C7 1.382(2) .
C7 H7 0.9300 .
C7 C8 1.383(2) .
C8 H8 0.9300 .
C9 C10 1.390(2) .
C9 C14 1.384(2) .
C10 H10 0.9300 .
C10 C11 1.385(2) .
C11 H11 0.9300 .
C11 C12 1.387(2) .
C12 C13 1.394(2) .
C12 C15 1.506(2) .
C13 H13 0.9300 .
C13 C14 1.389(2) .
C14 H14 0.9300 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
O1A C7A 1.2347(18) .
O2A H2A 1.06(3) .
O2A C7A 1.3047(17) .
O3A H3A 0.8200 .
O3A C2A 1.3453(18) .
C1A C2A 1.406(2) .
C1A C6A 1.397(2) .
C1A C7A 1.484(2) .
C2A C3A 1.397(2) .
C3A H3AA 0.9300 .
C3A C4A 1.372(2) .
C4A H4A 0.9300 .
C4A C5A 1.394(2) .
C5A H5A 0.9300 .
C5A C6A 1.380(2) .
C6A H6A 0.9300 .
