#------------------------------------------------------------------------------
#$Date: 2019-11-24 17:04:41 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238714 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/78/7237892.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_7237892
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 H F5 O), C30 H24 N4'
_chemical_formula_sum            'C42 H26 F10 N4 O2'
_chemical_formula_weight         808.67
_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             2019-02-01
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha                109.633(7)
_cell_angle_beta                 106.637(6)
_cell_angle_gamma                90.162(6)
_cell_formula_units_Z            1
_cell_length_a                   7.1878(5)
_cell_length_b                   11.3276(9)
_cell_length_c                   12.0753(8)
_cell_measurement_reflns_used    3211
_cell_measurement_temperature    123
_cell_measurement_theta_max      33.1400
_cell_measurement_theta_min      2.9740
_cell_volume                     881.90(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      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_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   15.00    --   30.00  54.00-120.00  193
  2  ω    -74.00 119.00   1.00   15.00    --   30.00  54.00   0.00  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      0.0528001000
_diffrn_orient_matrix_UB_12      0.0466618000
_diffrn_orient_matrix_UB_13      0.0571184000
_diffrn_orient_matrix_UB_21      0.0031100000
_diffrn_orient_matrix_UB_22      -0.0445882000
_diffrn_orient_matrix_UB_23      0.0298330000
_diffrn_orient_matrix_UB_31      0.0891031000
_diffrn_orient_matrix_UB_32      -0.0175607000
_diffrn_orient_matrix_UB_33      -0.0116632000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6129
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.976
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98667
_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    1.523
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0550P)²+0.3710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1006
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3074
_reflns_number_total             3562
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9tc02524c9.cif
_cod_data_source_block           yano092
_cod_database_code               7237892
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N O F'
_chemical_oxdiff_usercomment     'm-PyPP-F3 Phenol at 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
;
017dd93cddaff38a5250c3044ff5bad487003868488
;
_diffrn_oxdiff_ac3_digest_hkl
;
01e8f688b7f05794dfa5b3f38e0a52ca05a5c4
;
_reflns_odcompleteness_completeness 99.39
_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:
 C5(H5), C3(H3), C8(H8), C10(H10), C14(H14), C13(H13), C7(H7), C11(H11), C6(H6)
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 1.049
_oxdiff_exptl_absorpt_empirical_full_min 0.953
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
F6A F 0.18226(13) 0.42904(7) 0.19215(7) 0.0256(2) Uani 1 1 d .
F2A F 0.29030(15) 0.81176(8) 0.53112(7) 0.0310(2) Uani 1 1 d .
F4A F 0.29832(14) 0.81640(8) 0.14488(8) 0.0308(2) Uani 1 1 d .
F3A F 0.32843(14) 0.94056(8) 0.38694(8) 0.0290(2) Uani 1 1 d .
F5A F 0.22307(15) 0.56061(8) 0.04897(8) 0.0344(2) Uani 1 1 d .
O1A O 0.22303(15) 0.54456(9) 0.43454(9) 0.0231(2) Uani 1 1 d .
N1 N 0.83894(16) 0.91687(10) 1.03727(10) 0.0168(2) Uani 1 1 d .
N2 N 0.31815(17) 0.65285(11) 0.67153(10) 0.0215(3) Uani 1 1 d .
C1 C 1.00167(19) 0.99580(12) 1.05601(11) 0.0161(3) Uani 1 1 d .
C4 C 0.54480(19) 0.80081(12) 0.85536(12) 0.0165(3) Uani 1 1 d .
C5 C 0.4933(2) 0.71936(13) 0.73245(12) 0.0185(3) Uani 1 1 d .
H5 H 0.587940 0.710829 0.689940 0.022 Uiso 1 1 calc R
C3 C 0.83124(19) 0.93021(12) 0.85146(12) 0.0172(3) Uani 1 1 d .
H3 H 0.792364 0.919338 0.766227 0.021 Uiso 1 1 calc R
C1A C 0.24155(19) 0.61508(13) 0.36798(12) 0.0176(3) Uani 1 1 d .
C9 C 0.81295(19) 0.86799(13) 1.12759(12) 0.0163(3) Uani 1 1 d .
C2 C 0.73537(19) 0.87658(12) 0.91063(11) 0.0166(3) Uani 1 1 d .
C3A C 0.2943(2) 0.81400(13) 0.33875(13) 0.0200(3) Uani 1 1 d .
C8 C 0.4040(2) 0.80958(13) 0.91644(12) 0.0188(3) Uani 1 1 d .
H8 H 0.431150 0.864426 0.999730 0.023 Uiso 1 1 calc R
C6A C 0.22262(19) 0.55561(12) 0.24277(12) 0.0182(3) Uani 1 1 d .
C4A C 0.2790(2) 0.75180(14) 0.21668(13) 0.0211(3) Uani 1 1 d .
C2A C 0.2753(2) 0.74650(13) 0.41225(12) 0.0194(3) Uani 1 1 d .
C12 C 0.78314(19) 0.77427(14) 1.31021(13) 0.0204(3) Uani 1 1 d .
C10 C 0.8261(2) 0.95094(13) 1.24496(12) 0.0207(3) Uani 1 1 d .
H10 H 0.844652 1.039393 1.263682 0.025 Uiso 1 1 calc R
C14 C 0.78224(19) 0.73850(13) 1.10034(12) 0.0188(3) Uani 1 1 d .
H14 H 0.772869 0.681522 1.020076 0.023 Uiso 1 1 calc R
C5A C 0.2422(2) 0.62224(14) 0.16888(12) 0.0216(3) Uani 1 1 d .
C13 C 0.7653(2) 0.69276(13) 1.19106(13) 0.0207(3) Uani 1 1 d .
H13 H 0.741190 0.604462 1.171315 0.025 Uiso 1 1 calc R
C7 C 0.2241(2) 0.73748(14) 0.85434(13) 0.0212(3) Uani 1 1 d .
H7 H 0.128835 0.740389 0.895579 0.025 Uiso 1 1 calc R
C11 C 0.8119(2) 0.90331(14) 1.33516(12) 0.0225(3) Uani 1 1 d .
H11 H 0.822076 0.960329 1.415550 0.027 Uiso 1 1 calc R
C6 C 0.1850(2) 0.66129(14) 0.73171(13) 0.0221(3) Uani 1 1 d .
H6 H 0.060569 0.613695 0.688968 0.027 Uiso 1 1 calc R
C15 C 0.7745(2) 0.72355(16) 1.41013(14) 0.0277(3) Uani 1 1 d .
H15A H 0.673558 0.651510 1.375146 0.041 Uiso 1 1 calc GR
H15B H 0.742988 0.789818 1.476670 0.041 Uiso 1 1 calc GR
H15C H 0.901441 0.696519 1.443171 0.041 Uiso 1 1 calc GR
H1A H 0.261(4) 0.590(2) 0.527(2) 0.068(7) 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'
F F 0.0171 0.0103 '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 116.0(14) . .
C1 N1 C9 123.71(11) . .
C1 N1 C2 106.89(10) . .
C2 N1 C9 128.12(11) . .
C5 N2 C6 118.79(12) . .
N1 C1 C3 142.35(12) . 2_777
C1 C1 N1 108.39(14) 2_777 .
C1 C1 C3 109.26(14) 2_777 2_777
C5 C4 C2 119.16(12) . .
C5 C4 C8 117.00(12) . .
C8 C4 C2 123.75(12) . .
N2 C5 C4 123.54(12) . .
N2 C5 H5 118.2 . .
C4 C5 H5 118.2 . .
C1 C3 H3 127.1 2_777 .
C2 C3 C1 105.80(11) . 2_777
C2 C3 H3 127.1 . .
O1A C1A C6A 119.06(12) . .
O1A C1A C2A 125.46(12) . .
C2A C1A C6A 115.47(12) . .
C10 C9 N1 119.31(12) . .
C10 C9 C14 119.88(12) . .
C14 C9 N1 120.77(12) . .
N1 C2 C4 123.72(11) . .
C3 C2 N1 109.66(11) . .
C3 C2 C4 126.31(12) . .
F3A C3A C4A 119.99(12) . .
F3A C3A C2A 119.96(12) . .
C4A C3A C2A 120.06(13) . .
C4 C8 H8 120.3 . .
C7 C8 C4 119.46(12) . .
C7 C8 H8 120.3 . .
F6A C6A C1A 118.92(12) . .
F6A C6A C5A 118.88(12) . .
C5A C6A C1A 122.20(13) . .
F4A C4A C3A 120.48(13) . .
F4A C4A C5A 120.46(12) . .
C3A C4A C5A 119.06(13) . .
F2A C2A C1A 119.47(12) . .
F2A C2A C3A 117.85(12) . .
C3A C2A C1A 122.68(12) . .
C13 C12 C15 120.84(13) . .
C11 C12 C13 118.08(12) . .
C11 C12 C15 121.07(13) . .
C9 C10 H10 120.3 . .
C9 C10 C11 119.45(13) . .
C11 C10 H10 120.3 . .
C9 C14 H14 120.1 . .
C13 C14 C9 119.85(12) . .
C13 C14 H14 120.1 . .
F5A C5A C6A 119.93(13) . .
F5A C5A C4A 119.55(12) . .
C4A C5A C6A 120.51(12) . .
C12 C13 C14 121.13(13) . .
C12 C13 H13 119.4 . .
C14 C13 H13 119.4 . .
C8 C7 H7 120.3 . .
C6 C7 C8 119.37(13) . .
C6 C7 H7 120.3 . .
C12 C11 C10 121.58(13) . .
C12 C11 H11 119.2 . .
C10 C11 H11 119.2 . .
N2 C6 C7 121.79(13) . .
N2 C6 H6 119.1 . .
C7 C6 H6 119.1 . .
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
F6A C6A 1.3493(16) .
F2A C2A 1.3479(15) .
F4A C4A 1.3421(16) .
F3A C3A 1.3452(16) .
F5A C5A 1.3450(15) .
O1A C1A 1.3394(16) .
O1A H1A 1.01(2) .
N1 C1 1.3876(17) .
N1 C9 1.4328(16) .
N1 C2 1.4065(16) .
N2 C5 1.3363(18) .
N2 C6 1.3438(18) .
C1 C1 1.381(2) 2_777
C1 C3 1.4107(18) 2_777
C4 C5 1.3981(18) .
C4 C2 1.4640(18) .
C4 C8 1.3992(19) .
C5 H5 0.9500 .
C3 H3 0.9500 .
C3 C2 1.3876(18) .
C1A C6A 1.3984(18) .
C1A C2A 1.3963(19) .
C9 C10 1.3887(18) .
C9 C14 1.3931(19) .
C3A C4A 1.375(2) .
C3A C2A 1.384(2) .
C8 H8 0.9500 .
C8 C7 1.388(2) .
C6A C5A 1.3819(19) .
C4A C5A 1.378(2) .
C12 C13 1.3929(19) .
C12 C11 1.392(2) .
C12 C15 1.5161(18) .
C10 H10 0.9500 .
C10 C11 1.3951(19) .
C14 H14 0.9500 .
C14 C13 1.3930(19) .
C13 H13 0.9500 .
C7 H7 0.9500 .
C7 C6 1.385(2) .
C11 H11 0.9500 .
C6 H6 0.9500 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
