#------------------------------------------------------------------------------
#$Date: 2019-11-24 17:04:24 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238712 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/78/7237891.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_7237891
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(C6 H6 O)'
_chemical_formula_sum            'C42 H36 N4 O2'
_chemical_formula_weight         628.75
_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             2019-02-16
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha                93.146(6)
_cell_angle_beta                 90.933(6)
_cell_angle_gamma                112.034(7)
_cell_formula_units_Z            1
_cell_length_a                   8.9338(7)
_cell_length_b                   9.6930(8)
_cell_length_c                   10.7136(8)
_cell_measurement_reflns_used    1566
_cell_measurement_temperature    298
_cell_measurement_theta_max      22.8660
_cell_measurement_theta_min      2.8440
_cell_volume                     858.01(12)
_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      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 6.827
_diffrn_detector_type            CCD
_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   75.00    --   30.00  54.00 120.00  193
  2  ω    -71.00  31.00   1.00   75.00    --   30.00  54.00   0.00  102
  3  ω    -72.00  31.00   1.00   75.00    --   30.00  54.00-120.00  103
  4  ω    -74.00  32.00   1.00   75.00    --   30.00  54.00 120.00  106
;
_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      0.0047199000
_diffrn_orient_matrix_UB_12      0.0400969000
_diffrn_orient_matrix_UB_13      0.0582959000
_diffrn_orient_matrix_UB_21      -0.0684798000
_diffrn_orient_matrix_UB_22      -0.0595117000
_diffrn_orient_matrix_UB_23      0.0194681000
_diffrn_orient_matrix_UB_31      0.0513420000
_diffrn_orient_matrix_UB_32      -0.0333108000
_diffrn_orient_matrix_UB_33      0.0250202000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7709
_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         26.367
_diffrn_reflns_theta_min         2.647
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98877
_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    1.217
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3502
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0510
_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)+(0.0470P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1420
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1980
_reflns_number_total             3502
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9tc02524c6.cif
_cod_data_source_block           yano104
_cod_database_code               7237891
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_usercomment     'm-PyPP-Phenol 298 K'
_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
;
017f92f5643da8897dfbbf7e4edc0fc6df0050414c5
;
_diffrn_oxdiff_ac3_digest_hkl
;
0125ec1ed91202df8e5f0f222143a04593231d
;
_reflns_odcompleteness_completeness 99.89
_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
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C10(H10), C13(H13), C8(H8), C11(H11), C5(H5), C6A(H6A),
 C7(H7), C2A(H2A), C6(H6), C5A(H5A), C4A(H4A), C3A(H3A)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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 1.078
_oxdiff_exptl_absorpt_empirical_full_min 0.920
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 0.84804(19) 0.88038(18) 0.58536(15) 0.0425(4) Uani 1 1 d .
O1A O 0.3553(2) 0.2194(2) 0.69288(18) 0.0819(6) Uani 1 1 d .
N2 N 0.6692(2) 0.4089(2) 0.6685(2) 0.0691(6) Uani 1 1 d .
C1 C 0.9312(2) 1.0070(2) 0.52253(17) 0.0420(5) Uani 1 1 d .
C9 C 0.7166(2) 0.8688(2) 0.66348(19) 0.0411(5) Uani 1 1 d .
C4 C 0.8843(2) 0.6391(2) 0.62245(19) 0.0439(5) Uani 1 1 d .
C2 C 0.9380(2) 0.7881(2) 0.57689(18) 0.0430(5) Uani 1 1 d .
C3 C 1.0741(2) 0.8567(2) 0.51026(18) 0.0449(5) Uani 1 1 d .
H3 H 1.153796 0.819807 0.490892 0.054 Uiso 1 1 calc R
C14 C 0.7191(3) 0.8320(2) 0.78696(19) 0.0483(5) Uani 1 1 d .
H14 H 0.806253 0.813040 0.819151 0.058 Uiso 1 1 calc R
C12 C 0.4629(3) 0.8577(2) 0.8180(2) 0.0518(6) Uani 1 1 d .
C10 C 0.5889(2) 0.9009(2) 0.6183(2) 0.0515(6) Uani 1 1 d .
H10 H 0.585716 0.924901 0.535691 0.062 Uiso 1 1 calc R
C13 C 0.5919(3) 0.8238(2) 0.8617(2) 0.0523(6) Uani 1 1 d .
H13 H 0.592374 0.795048 0.943043 0.063 Uiso 1 1 calc R
C8 C 0.9960(3) 0.5802(2) 0.6621(2) 0.0532(6) Uani 1 1 d .
H8 H 1.106060 0.636444 0.659879 0.064 Uiso 1 1 calc R
C11 C 0.4654(3) 0.8974(3) 0.6957(2) 0.0589(6) Uani 1 1 d .
H11 H 0.381681 0.922407 0.664746 0.071 Uiso 1 1 calc R
C1A C 0.2786(3) 0.2605(3) 0.7879(2) 0.0570(6) Uani 1 1 d .
C5 C 0.7222(3) 0.5458(2) 0.6257(2) 0.0581(6) Uani 1 1 d .
H5 H 0.645436 0.580829 0.596156 0.070 Uiso 1 1 calc R
C6A C 0.1303(3) 0.1579(3) 0.8202(2) 0.0594(6) Uani 1 1 d .
H6A H 0.086993 0.064684 0.777128 0.071 Uiso 1 1 calc R
C7 C 0.9437(3) 0.4383(3) 0.7047(2) 0.0648(7) Uani 1 1 d .
H7 H 1.017624 0.398077 0.730571 0.078 Uiso 1 1 calc R
C2A C 0.3401(3) 0.3991(3) 0.8518(2) 0.0647(7) Uani 1 1 d .
H2A H 0.438074 0.469901 0.830084 0.078 Uiso 1 1 calc R
C6 C 0.7810(3) 0.3581(3) 0.7082(2) 0.0679(7) Uani 1 1 d .
H6 H 0.746410 0.264064 0.739556 0.082 Uiso 1 1 calc R
C5A C 0.0473(3) 0.1932(3) 0.9156(2) 0.0656(7) Uani 1 1 d .
H5A H -0.051604 0.123467 0.936828 0.079 Uiso 1 1 calc R
C4A C 0.1090(3) 0.3305(3) 0.9799(2) 0.0696(7) Uani 1 1 d .
H4A H 0.052205 0.354340 1.044049 0.083 Uiso 1 1 calc R
C3A C 0.2556(3) 0.4321(3) 0.9482(2) 0.0713(7) Uani 1 1 d .
H3A H 0.298750 0.524619 0.992326 0.086 Uiso 1 1 calc R
C15 C 0.3258(3) 0.8525(3) 0.9008(2) 0.0766(8) Uani 1 1 d .
H15A H 0.232314 0.764648 0.877368 0.115 Uiso 1 1 calc GR
H15B H 0.300616 0.939407 0.891129 0.115 Uiso 1 1 calc GR
H15C H 0.357251 0.850163 0.986532 0.115 Uiso 1 1 calc GR
H1A H 0.464(4) 0.291(3) 0.680(3) 0.106(10) Uiso 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 C9 123.14(15) . .
C1 N1 C2 107.15(15) . .
C2 N1 C9 128.49(16) . .
C1A O1A H1A 114.6(17) . .
C5 N2 C6 117.3(2) . .
N1 C1 C3 142.74(17) . 2_776
C1 C1 N1 107.9(2) 2_776 .
C1 C1 C3 109.3(2) 2_776 2_776
C14 C9 N1 120.75(18) . .
C10 C9 N1 119.84(18) . .
C10 C9 C14 119.35(19) . .
C8 C4 C2 120.69(19) . .
C5 C4 C2 123.19(19) . .
C5 C4 C8 116.1(2) . .
N1 C2 C4 123.95(17) . .
C3 C2 N1 109.03(17) . .
C3 C2 C4 126.81(18) . .
C1 C3 H3 126.7 2_776 .
C2 C3 C1 106.56(18) . 2_776
C2 C3 H3 126.7 . .
C9 C14 H14 120.1 . .
C13 C14 C9 119.86(19) . .
C13 C14 H14 120.1 . .
C13 C12 C15 121.5(2) . .
C11 C12 C13 117.4(2) . .
C11 C12 C15 121.1(2) . .
C9 C10 H10 120.0 . .
C9 C10 C11 120.0(2) . .
C11 C10 H10 120.0 . .
C14 C13 C12 121.5(2) . .
C14 C13 H13 119.3 . .
C12 C13 H13 119.3 . .
C4 C8 H8 119.9 . .
C7 C8 C4 120.2(2) . .
C7 C8 H8 119.9 . .
C12 C11 H11 119.1 . .
C10 C11 C12 121.8(2) . .
C10 C11 H11 119.1 . .
O1A C1A C6A 117.8(2) . .
O1A C1A C2A 123.2(2) . .
C2A C1A C6A 119.0(2) . .
N2 C5 C4 124.5(2) . .
N2 C5 H5 117.8 . .
C4 C5 H5 117.8 . .
C1A C6A H6A 119.8 . .
C5A C6A C1A 120.3(2) . .
C5A C6A H6A 119.8 . .
C8 C7 H7 120.6 . .
C6 C7 C8 118.8(2) . .
C6 C7 H7 120.6 . .
C1A C2A H2A 120.1 . .
C1A C2A C3A 119.8(2) . .
C3A C2A H2A 120.1 . .
N2 C6 C7 123.0(2) . .
N2 C6 H6 118.5 . .
C7 C6 H6 118.5 . .
C6A C5A H5A 119.7 . .
C4A C5A C6A 120.7(2) . .
C4A C5A H5A 119.7 . .
C5A C4A H4A 120.5 . .
C3A C4A C5A 119.1(2) . .
C3A C4A H4A 120.5 . .
C2A C3A H3A 119.5 . .
C4A C3A C2A 121.1(3) . .
C4A C3A H3A 119.5 . .
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 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.391(2) .
N1 C9 1.427(2) .
N1 C2 1.410(2) .
O1A C1A 1.359(3) .
O1A H1A 0.98(3) .
N2 C5 1.341(3) .
N2 C6 1.341(3) .
C1 C1 1.379(4) 2_776
C1 C3 1.403(3) 2_776
C9 C14 1.391(3) .
C9 C10 1.378(3) .
C4 C2 1.455(3) .
C4 C8 1.394(3) .
C4 C5 1.392(3) .
C2 C3 1.380(3) .
C3 H3 0.9300 .
C14 H14 0.9300 .
C14 C13 1.382(3) .
C12 C13 1.391(3) .
C12 C11 1.384(3) .
C12 C15 1.512(3) .
C10 H10 0.9300 .
C10 C11 1.382(3) .
C13 H13 0.9300 .
C8 H8 0.9300 .
C8 C7 1.382(3) .
C11 H11 0.9300 .
C1A C6A 1.389(3) .
C1A C2A 1.381(3) .
C5 H5 0.9300 .
C6A H6A 0.9300 .
C6A C5A 1.374(3) .
C7 H7 0.9300 .
C7 C6 1.369(3) .
C2A H2A 0.9300 .
C2A C3A 1.382(3) .
C6 H6 0.9300 .
C5A H5A 0.9300 .
C5A C4A 1.373(3) .
C4A H4A 0.9300 .
C4A C3A 1.372(3) .
C3A H3A 0.9300 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
