#------------------------------------------------------------------------------
#$Date: 2019-11-24 17:01:11 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238692 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/78/7237879.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_7237879
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(C7 H6 O3), C30 H24 N4'
_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             2018-12-17
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha                116.795(11)
_cell_angle_beta                 95.657(9)
_cell_angle_gamma                102.311(9)
_cell_formula_units_Z            1
_cell_length_a                   6.5951(7)
_cell_length_b                   12.5932(13)
_cell_length_c                   13.1549(16)
_cell_measurement_reflns_used    2545
_cell_measurement_temperature    298
_cell_measurement_theta_max      30.6210
_cell_measurement_theta_min      3.0600
_cell_volume                     928.8(2)
_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_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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   29.27    --   30.00  54.00  30.00  193
  2  ω    -74.00 119.00   1.00   29.27    --   30.00  54.00 -90.00  193
  3  ω    -74.00  -4.00   1.00   29.27    --   30.00  54.00 150.00   70
;
_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      0.0140835000
_diffrn_orient_matrix_UB_12      -0.0193745000
_diffrn_orient_matrix_UB_13      -0.0578281000
_diffrn_orient_matrix_UB_21      0.0250743000
_diffrn_orient_matrix_UB_22      0.0625238000
_diffrn_orient_matrix_UB_23      0.0113678000
_diffrn_orient_matrix_UB_31      0.1092085000
_diffrn_orient_matrix_UB_32      0.0079199000
_diffrn_orient_matrix_UB_33      0.0191535000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7632
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.117
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97191
_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    1.281
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0424
_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)+(0.0710P)²+0.1390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1346
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2861
_reflns_number_total             3789
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9tc02524c15.cif
_cod_data_source_block           yano072
_cod_database_code               7237879
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'm-PyPP-Salicylic acid r.t.'
_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
;
01a211a9501cbd94f9e0beef5940a1daa500456e6f0
;
_diffrn_oxdiff_ac3_digest_hkl
;
019d32b34a047a26bcd1a1f2fe23573c08741f
;
_reflns_odcompleteness_completeness 99.66
_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), C8(H8), C10(H10), C7(H7), C5(H5), C6A(H6A), C14(H14), C6(H6),
 C11(H11), C5A(H5A), C13(H13), C3A(H3AA), C4A(H4A)
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 1.134
_oxdiff_exptl_absorpt_empirical_full_min 0.918
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
O2A O 0.77749(19) 0.03854(12) 0.18666(12) 0.0588(3) Uani 1 1 d .
N1 N 0.62637(19) 0.47317(11) 0.10396(10) 0.0390(3) Uani 1 1 d .
N2 N 0.8971(2) 0.17869(12) 0.09440(12) 0.0478(3) Uani 1 1 d .
O1A O 0.4677(2) 0.08253(15) 0.19181(14) 0.0808(5) Uani 1 1 d .
O3A O 0.1968(2) -0.01121(16) 0.28149(16) 0.0824(5) Uani 1 1 d .
H3A H 0.240202 0.027140 0.247701 0.124 Uiso 1 1 calc GR
C9 C 0.6912(2) 0.51614(13) 0.22629(12) 0.0389(3) Uani 1 1 d .
C4 C 0.8351(2) 0.31828(13) 0.02525(12) 0.0375(3) Uani 1 1 d .
C1 C 0.4997(2) 0.52362(13) 0.05830(12) 0.0370(3) Uani 1 1 d .
C3 C 0.6274(2) 0.39433(13) -0.08888(13) 0.0397(3) Uani 1 1 d .
H3 H 0.653677 0.349450 -0.162290 0.048 Uiso 1 1 calc R
C2 C 0.7042(2) 0.39440(13) 0.01220(13) 0.0381(3) Uani 1 1 d .
C8 C 1.0115(2) 0.30721(14) -0.02397(14) 0.0437(4) Uani 1 1 d .
H8 H 1.049901 0.349413 -0.064934 0.052 Uiso 1 1 calc R
C10 C 0.5391(3) 0.52049(15) 0.29149(14) 0.0487(4) Uani 1 1 d .
H10 H 0.395296 0.489559 0.255154 0.058 Uiso 1 1 calc R
C1A C 0.5483(2) -0.03703(14) 0.27954(14) 0.0439(4) Uani 1 1 d .
C7 C 1.1301(3) 0.23350(15) -0.01218(15) 0.0496(4) Uani 1 1 d .
H7 H 1.248496 0.225600 -0.044798 0.060 Uiso 1 1 calc R
C5 C 0.7832(3) 0.25022(14) 0.08314(14) 0.0444(4) Uani 1 1 d .
H5 H 0.663946 0.254855 0.115343 0.053 Uiso 1 1 calc R
C6A C 0.7016(3) -0.08253(15) 0.31429(15) 0.0487(4) Uani 1 1 d .
H6A H 0.833930 -0.070060 0.295608 0.058 Uiso 1 1 calc R
C7A C 0.5940(3) 0.03316(15) 0.21558(15) 0.0494(4) Uani 1 1 d .
C14 C 0.9048(3) 0.55978(16) 0.28109(15) 0.0522(4) Uani 1 1 d .
H14 H 1.008687 0.556815 0.237749 0.063 Uiso 1 1 calc R
C6 C 1.0691(3) 0.17192(15) 0.04897(15) 0.0503(4) Uani 1 1 d .
H6 H 1.150615 0.124052 0.058862 0.060 Uiso 1 1 calc R
C11 C 0.6012(3) 0.57113(17) 0.41142(15) 0.0571(5) Uani 1 1 d .
H11 H 0.497197 0.574842 0.454770 0.069 Uiso 1 1 calc R
C2A C 0.3501(3) -0.05637(16) 0.30848(16) 0.0524(4) Uani 1 1 d .
C5A C 0.6591(3) -0.14568(17) 0.37595(16) 0.0568(4) Uani 1 1 d .
H5A H 0.762387 -0.174976 0.399545 0.068 Uiso 1 1 calc R
C12 C 0.8130(3) 0.61631(16) 0.46869(15) 0.0598(5) Uani 1 1 d .
C13 C 0.9625(3) 0.60785(17) 0.40085(16) 0.0629(5) Uani 1 1 d .
H13 H 1.106169 0.635265 0.436747 0.076 Uiso 1 1 calc R
C3A C 0.3079(3) -0.12230(17) 0.36925(17) 0.0599(5) Uani 1 1 d .
H3AA H 0.175292 -0.137035 0.387097 0.072 Uiso 1 1 calc R
C4A C 0.4611(3) -0.16503(16) 0.40238(16) 0.0582(5) Uani 1 1 d .
H4A H 0.431995 -0.208057 0.443567 0.070 Uiso 1 1 calc R
C15 C 0.8791(5) 0.6759(2) 0.60063(17) 0.0953(8) Uani 1 1 d .
H15A H 0.949958 0.762842 0.632827 0.143 Uiso 1 1 calc GR
H15B H 0.974069 0.636731 0.620730 0.143 Uiso 1 1 calc GR
H15C H 0.755153 0.665746 0.631796 0.143 Uiso 1 1 calc GR
H2A H 0.816(4) 0.097(2) 0.150(2) 0.106(8) 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
C7A O2A H2A 114.2(13) . .
C1 N1 C9 123.52(12) . .
C1 N1 C2 107.07(11) . .
C2 N1 C9 128.39(11) . .
C6 N2 C5 118.94(13) . .
C2A O3A H3A 109.5 . .
C10 C9 N1 119.35(13) . .
C10 C9 C14 119.59(14) . .
C14 C9 N1 120.97(14) . .
C8 C4 C2 121.14(12) . .
C8 C4 C5 117.05(13) . .
C5 C4 C2 121.76(13) . .
N1 C1 C3 142.65(13) . 2_665
C1 C1 N1 107.87(15) 2_665 .
C1 C1 C3 109.48(15) 2_665 2_665
C1 C3 H3 127.1 2_665 .
C2 C3 C1 105.85(13) . 2_665
C2 C3 H3 127.1 . .
N1 C2 C4 123.01(12) . .
C3 C2 N1 109.74(12) . .
C3 C2 C4 127.11(13) . .
C4 C8 H8 120.0 . .
C7 C8 C4 120.10(14) . .
C7 C8 H8 120.0 . .
C9 C10 H10 120.2 . .
C9 C10 C11 119.69(16) . .
C11 C10 H10 120.2 . .
C6A C1A C7A 121.16(14) . .
C6A C1A C2A 118.93(15) . .
C2A C1A C7A 119.90(14) . .
C8 C7 H7 120.7 . .
C6 C7 C8 118.64(15) . .
C6 C7 H7 120.7 . .
N2 C5 C4 122.98(14) . .
N2 C5 H5 118.5 . .
C4 C5 H5 118.5 . .
C1A C6A H6A 119.6 . .
C5A C6A C1A 120.76(16) . .
C5A C6A H6A 119.6 . .
O2A C7A C1A 114.61(13) . .
O1A C7A O2A 122.93(15) . .
O1A C7A C1A 122.46(16) . .
C9 C14 H14 120.2 . .
C13 C14 C9 119.55(17) . .
C13 C14 H14 120.2 . .
N2 C6 C7 122.26(14) . .
N2 C6 H6 118.9 . .
C7 C6 H6 118.9 . .
C10 C11 H11 119.0 . .
C12 C11 C10 122.04(17) . .
C12 C11 H11 119.0 . .
O3A C2A C1A 122.23(16) . .
O3A C2A C3A 118.04(16) . .
C3A C2A C1A 119.72(16) . .
C6A C5A H5A 120.4 . .
C6A C5A C4A 119.29(17) . .
C4A C5A H5A 120.4 . .
C11 C12 C13 117.12(16) . .
C11 C12 C15 121.5(2) . .
C13 C12 C15 121.4(2) . .
C14 C13 H13 119.0 . .
C12 C13 C14 121.97(17) . .
C12 C13 H13 119.0 . .
C2A C3A H3AA 120.0 . .
C4A C3A C2A 119.96(16) . .
C4A C3A H3AA 120.0 . .
C5A C4A H4A 119.3 . .
C3A C4A C5A 121.33(16) . .
C3A C4A H4A 119.3 . .
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
O2A C7A 1.301(2) .
O2A H2A 1.05(3) .
N1 C9 1.4303(18) .
N1 C1 1.3905(17) .
N1 C2 1.4015(19) .
N2 C5 1.3358(18) .
N2 C6 1.334(2) .
O1A C7A 1.2339(19) .
O3A H3A 0.8200 .
O3A C2A 1.352(2) .
C9 C10 1.377(2) .
C9 C14 1.385(2) .
C4 C2 1.4720(19) .
C4 C8 1.388(2) .
C4 C5 1.395(2) .
C1 C1 1.373(3) 2_665
C1 C3 1.4116(19) 2_665
C3 H3 0.9300 .
C3 C2 1.3751(19) .
C8 H8 0.9300 .
C8 C7 1.383(2) .
C10 H10 0.9300 .
C10 C11 1.385(2) .
C1A C6A 1.397(2) .
C1A C7A 1.479(2) .
C1A C2A 1.399(2) .
C7 H7 0.9300 .
C7 C6 1.380(2) .
C5 H5 0.9300 .
C6A H6A 0.9300 .
C6A C5A 1.379(2) .
C14 H14 0.9300 .
C14 C13 1.385(2) .
C6 H6 0.9300 .
C11 H11 0.9300 .
C11 C12 1.382(3) .
C2A C3A 1.396(3) .
C5A H5A 0.9300 .
C5A C4A 1.384(3) .
C12 C13 1.383(3) .
C12 C15 1.517(3) .
C13 H13 0.9300 .
C3A H3AA 0.9300 .
C3A C4A 1.363(3) .
C4A H4A 0.9300 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
