#------------------------------------------------------------------------------
#$Date: 2019-11-24 17:04:14 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238711 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/78/7237890.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_7237890
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         '2(C6 H6 O), C30 H24 N4'
_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             2019-02-15
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha                93.787(5)
_cell_angle_beta                 91.373(5)
_cell_angle_gamma                112.630(6)
_cell_formula_units_Z            1
_cell_length_a                   8.8912(5)
_cell_length_b                   9.5438(6)
_cell_length_c                   10.6502(7)
_cell_measurement_reflns_used    2500
_cell_measurement_temperature    123
_cell_measurement_theta_max      32.4470
_cell_measurement_theta_min      2.8610
_cell_volume                     831.13(10)
_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_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 -60.00  193
  2  ω    -74.00 119.00   1.00   75.00    --   30.00  54.00  30.00  193
  3  ω    -74.00 119.00   1.00   75.00    --   30.00  54.00-180.00  193
;
_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      0.0086605000
_diffrn_orient_matrix_UB_12      0.0409827000
_diffrn_orient_matrix_UB_13      0.0595692000
_diffrn_orient_matrix_UB_21      -0.0694638000
_diffrn_orient_matrix_UB_22      -0.0598948000
_diffrn_orient_matrix_UB_23      0.0197940000
_diffrn_orient_matrix_UB_31      0.0509067000
_diffrn_orient_matrix_UB_32      -0.0354963000
_diffrn_orient_matrix_UB_33      0.0229680000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8591
_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         26.366
_diffrn_reflns_theta_min         2.663
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98301
_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    1.256
_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         0.198
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0414
_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)+(0.0430P)²+0.1380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.1030
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2442
_reflns_number_total             3388
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9tc02524c5.cif
_cod_data_source_block           yano103
_cod_database_code               7237890
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'm-PyPP-Phenol 123 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
;
01113ec7d0e422ef83b370d06ec96478270057974c4
;
_diffrn_oxdiff_ac3_digest_hkl
;
015940d6b04693e6405e6861f1c0cc8ade7d87
;
_reflns_odcompleteness_completeness 99.91
_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:
 C14(H14), C10(H10), C3(H3), C13(H13), C8(H8), C11(H11), C5(H5), C6A(H6A),
 C7(H7), C2A(H2A), C5A(H5A), C3A(H3A), C6(H6), C4A(H4A)
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 1.040
_oxdiff_exptl_absorpt_empirical_full_min 0.955
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
O1A O 0.64469(15) 0.78974(14) 0.30450(11) 0.0348(3) Uani 1 1 d .
N1 N 0.15250(15) 0.12215(14) 0.41501(12) 0.0197(3) Uani 1 1 d .
N2 N 0.32702(17) 0.59941(15) 0.32449(13) 0.0296(3) Uani 1 1 d .
C1 C 0.06981(18) -0.00588(17) 0.47791(14) 0.0201(3) Uani 1 1 d .
C9 C 0.28362(17) 0.13343(16) 0.33559(14) 0.0193(3) Uani 1 1 d .
C2 C 0.06022(18) 0.21337(17) 0.42184(14) 0.0201(3) Uani 1 1 d .
C4 C 0.11267(18) 0.36495(17) 0.37445(14) 0.0208(3) Uani 1 1 d .
C12 C 0.53708(19) 0.14305(17) 0.18017(15) 0.0229(4) Uani 1 1 d .
C14 C 0.28023(19) 0.17029(17) 0.21196(15) 0.0220(3) Uani 1 1 d .
H14 H 0.191018 0.190627 0.179238 0.026 Uiso 1 1 calc R
C10 C 0.41297(18) 0.10091(18) 0.38226(15) 0.0230(3) Uani 1 1 d .
H10 H 0.416896 0.077070 0.467164 0.028 Uiso 1 1 calc R
C3 C -0.07768(18) 0.14320(17) 0.48808(14) 0.0209(3) Uani 1 1 d .
H3 H -0.160472 0.180105 0.506721 0.025 Uiso 1 1 calc R
C13 C 0.40736(19) 0.17738(17) 0.13624(15) 0.0238(4) Uani 1 1 d .
H13 H 0.405947 0.206240 0.052680 0.029 Uiso 1 1 calc R
C8 C -0.0030(2) 0.42171(18) 0.33642(14) 0.0230(3) Uani 1 1 d .
H8 H -0.116022 0.362347 0.341333 0.028 Uiso 1 1 calc R
C11 C 0.53659(19) 0.10356(18) 0.30364(15) 0.0252(4) Uani 1 1 d .
H11 H 0.622745 0.077784 0.335006 0.030 Uiso 1 1 calc R
C5 C 0.27662(19) 0.46124(18) 0.36933(15) 0.0255(4) Uani 1 1 d .
H5 H 0.357124 0.427094 0.399273 0.031 Uiso 1 1 calc R
C1A C 0.72121(19) 0.74438(18) 0.21052(15) 0.0244(4) Uani 1 1 d .
C6A C 0.87155(19) 0.84816(18) 0.17753(15) 0.0258(4) Uani 1 1 d .
H6A H 0.917658 0.946819 0.220672 0.031 Uiso 1 1 calc R
C7 C 0.0477(2) 0.56489(18) 0.29150(15) 0.0274(4) Uani 1 1 d .
H7 H -0.029799 0.604707 0.265506 0.033 Uiso 1 1 calc R
C2A C 0.65510(19) 0.59970(18) 0.14620(15) 0.0271(4) Uani 1 1 d .
H2A H 0.553291 0.527390 0.168387 0.033 Uiso 1 1 calc R
C5A C 0.9542(2) 0.80797(19) 0.08188(16) 0.0282(4) Uani 1 1 d .
H5A H 1.056978 0.879294 0.060405 0.034 Uiso 1 1 calc R
C3A C 0.7386(2) 0.56176(19) 0.04964(16) 0.0301(4) Uani 1 1 d .
H3A H 0.692255 0.463833 0.005280 0.036 Uiso 1 1 calc R
C6 C 0.2127(2) 0.64859(18) 0.28519(16) 0.0286(4) Uani 1 1 d .
H6 H 0.246857 0.745121 0.251601 0.034 Uiso 1 1 calc R
C4A C 0.8884(2) 0.66474(19) 0.01727(16) 0.0297(4) Uani 1 1 d .
H4A H 0.945222 0.637704 -0.048247 0.036 Uiso 1 1 calc R
C15 C 0.6746(2) 0.1487(2) 0.09696(17) 0.0324(4) Uani 1 1 d .
H15A H 0.635810 0.134334 0.008299 0.049 Uiso 1 1 calc GR
H15B H 0.711546 0.067539 0.115824 0.049 Uiso 1 1 calc GR
H15C H 0.765569 0.247723 0.112878 0.049 Uiso 1 1 calc GR
H1A H 0.533(3) 0.715(2) 0.311(2) 0.057(6) 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
C1A O1A H1A 111.2(12) . .
C1 N1 C9 123.08(12) . .
C1 N1 C2 106.97(12) . .
C2 N1 C9 128.40(12) . .
C6 N2 C5 117.84(14) . .
N1 C1 C3 142.35(13) . 2_556
C1 C1 N1 108.28(16) 2_556 .
C1 C1 C3 109.36(16) 2_556 2_556
C14 C9 N1 121.07(13) . .
C14 C9 C10 119.81(14) . .
C10 C9 N1 119.07(13) . .
N1 C2 C4 123.90(13) . .
C3 C2 N1 109.53(13) . .
C3 C2 C4 126.37(13) . .
C8 C4 C2 120.24(14) . .
C8 C4 C5 116.78(14) . .
C5 C4 C2 122.93(13) . .
C13 C12 C15 121.39(15) . .
C11 C12 C13 117.80(14) . .
C11 C12 C15 120.81(14) . .
C9 C14 H14 120.1 . .
C13 C14 C9 119.88(14) . .
C13 C14 H14 120.1 . .
C9 C10 H10 120.3 . .
C9 C10 C11 119.48(15) . .
C11 C10 H10 120.3 . .
C1 C3 H3 127.1 2_556 .
C2 C3 C1 105.85(13) . 2_556
C2 C3 H3 127.1 . .
C12 C13 H13 119.3 . .
C14 C13 C12 121.38(15) . .
C14 C13 H13 119.3 . .
C4 C8 H8 120.1 . .
C7 C8 C4 119.84(15) . .
C7 C8 H8 120.1 . .
C12 C11 H11 119.2 . .
C10 C11 C12 121.58(14) . .
C10 C11 H11 119.2 . .
N2 C5 C4 123.78(15) . .
N2 C5 H5 118.1 . .
C4 C5 H5 118.1 . .
O1A C1A C6A 117.94(15) . .
O1A C1A C2A 122.89(15) . .
C6A C1A C2A 119.17(15) . .
C1A C6A H6A 119.9 . .
C5A C6A C1A 120.25(16) . .
C5A C6A H6A 119.9 . .
C8 C7 H7 120.6 . .
C6 C7 C8 118.86(15) . .
C6 C7 H7 120.6 . .
C1A C2A H2A 120.1 . .
C3A C2A C1A 119.88(15) . .
C3A C2A H2A 120.1 . .
C6A C5A H5A 119.6 . .
C6A C5A C4A 120.71(15) . .
C4A C5A H5A 119.6 . .
C2A C3A H3A 119.5 . .
C4A C3A C2A 120.92(16) . .
C4A C3A H3A 119.5 . .
N2 C6 C7 122.80(15) . .
N2 C6 H6 118.6 . .
C7 C6 H6 118.6 . .
C5A C4A H4A 120.5 . .
C3A C4A C5A 119.06(16) . .
C3A C4A H4A 120.5 . .
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
O1A C1A 1.3617(19) .
O1A H1A 0.98(2) .
N1 C1 1.3866(18) .
N1 C9 1.4314(18) .
N1 C2 1.4073(18) .
N2 C5 1.344(2) .
N2 C6 1.342(2) .
C1 C1 1.380(3) 2_556
C1 C3 1.409(2) 2_556
C9 C14 1.388(2) .
C9 C10 1.391(2) .
C2 C4 1.467(2) .
C2 C3 1.386(2) .
C4 C8 1.397(2) .
C4 C5 1.397(2) .
C12 C13 1.393(2) .
C12 C11 1.391(2) .
C12 C15 1.514(2) .
C14 H14 0.9500 .
C14 C13 1.387(2) .
C10 H10 0.9500 .
C10 C11 1.391(2) .
C3 H3 0.9500 .
C13 H13 0.9500 .
C8 H8 0.9500 .
C8 C7 1.386(2) .
C11 H11 0.9500 .
C5 H5 0.9500 .
C1A C6A 1.393(2) .
C1A C2A 1.397(2) .
C6A H6A 0.9500 .
C6A C5A 1.388(2) .
C7 H7 0.9500 .
C7 C6 1.380(2) .
C2A H2A 0.9500 .
C2A C3A 1.391(2) .
C5A H5A 0.9500 .
C5A C4A 1.388(2) .
C3A H3A 0.9500 .
C3A C4A 1.385(2) .
C6 H6 0.9500 .
C4A H4A 0.9500 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
