#------------------------------------------------------------------------------
#$Date: 2019-11-24 16:59:05 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238684 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/78/7237876.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_7237876
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             2019-01-31
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha                109.165(5)
_cell_angle_beta                 106.484(5)
_cell_angle_gamma                91.817(5)
_cell_formula_units_Z            1
_cell_length_a                   7.3417(4)
_cell_length_b                   11.3589(7)
_cell_length_c                   12.1244(7)
_cell_measurement_reflns_used    2872
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.3260
_cell_measurement_theta_min      2.9260
_cell_volume                     907.06(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      298
_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   17.17    --   30.00  54.00 120.00  193
  2  ω    -71.00  32.00   1.00   17.17    --   30.00  54.00-120.00  103
  3  ω    -70.00  30.00   1.00   17.17    --   30.00  54.00   0.00  100
  4  ω    -73.00  29.00   1.00   17.17    --   30.00  54.00 120.00  102
;
_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      0.0539235000
_diffrn_orient_matrix_UB_12      0.0464089000
_diffrn_orient_matrix_UB_13      0.0568546000
_diffrn_orient_matrix_UB_21      0.0091018000
_diffrn_orient_matrix_UB_22      -0.0460675000
_diffrn_orient_matrix_UB_23      0.0282999000
_diffrn_orient_matrix_UB_31      0.0857757000
_diffrn_orient_matrix_UB_32      -0.0133758000
_diffrn_orient_matrix_UB_33      -0.0146609000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8137
_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         26.372
_diffrn_reflns_theta_min         2.921
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99921
_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    1.480
_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         0.175
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0387
_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)+(0.0530P)²+0.2440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2872
_reflns_number_total             3695
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9tc02524c10.cif
_cod_data_source_block           yano091
_cod_database_code               7237876
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N O F'
_chemical_oxdiff_usercomment     'm-PyPP-F3 Phenol at 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
;
01368098ca4757a0845cd609f06a94456b00498cc31
;
_diffrn_oxdiff_ac3_digest_hkl
;
01b5d94c8b9123856c9c70dd44ce86c389348c
;
_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), C5(H5), C8(H8), C14(H14), C10(H10), C13(H13), C6(H6), C11(H11), C7(H7)
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 1.037
_oxdiff_exptl_absorpt_empirical_full_min 0.978
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 0.18554(17) 0.43206(9) 0.19557(9) 0.0602(3) Uani 1 1 d .
F2A F 0.2872(2) 0.81337(10) 0.52956(9) 0.0698(3) Uani 1 1 d .
F3A F 0.32633(18) 0.94217(9) 0.38593(10) 0.0677(3) Uani 1 1 d .
F4A F 0.2989(2) 0.81878(11) 0.14660(11) 0.0726(4) Uani 1 1 d .
O1A O 0.22142(19) 0.54726(11) 0.43492(11) 0.0532(3) Uani 1 1 d .
F5A F 0.2261(2) 0.56357(11) 0.05256(10) 0.0802(4) Uani 1 1 d .
N1 N 0.83853(17) 0.91693(11) 1.03721(10) 0.0358(3) Uani 1 1 d .
N2 N 0.3181(2) 0.65555(13) 0.67247(12) 0.0469(3) Uani 1 1 d .
C1 C 1.0011(2) 0.99593(13) 1.05560(13) 0.0342(3) Uani 1 1 d .
C4 C 0.5465(2) 0.80098(13) 0.85598(13) 0.0350(3) Uani 1 1 d .
C9 C 0.8124(2) 0.86717(14) 1.12679(13) 0.0336(3) Uani 1 1 d .
C2 C 0.7367(2) 0.87625(13) 0.91101(13) 0.0349(3) Uani 1 1 d .
C3 C 0.8329(2) 0.92969(14) 0.85266(13) 0.0369(3) Uani 1 1 d .
H3 H 0.795717 0.918770 0.769549 0.044 Uiso 1 1 calc R
C1A C 0.2410(2) 0.61776(14) 0.36861(13) 0.0384(3) Uani 1 1 d .
C5 C 0.4924(2) 0.72049(15) 0.73363(14) 0.0409(4) Uani 1 1 d .
H5 H 0.583301 0.711668 0.692432 0.049 Uiso 1 1 calc R
C8 C 0.4089(2) 0.80962(15) 0.91618(14) 0.0412(4) Uani 1 1 d .
H8 H 0.437493 0.862440 0.997654 0.049 Uiso 1 1 calc R
C3A C 0.2931(2) 0.81575(15) 0.33868(15) 0.0444(4) Uani 1 1 d .
C12 C 0.7827(2) 0.77189(17) 1.30777(15) 0.0441(4) Uani 1 1 d .
C2A C 0.2742(2) 0.74865(15) 0.41204(14) 0.0431(4) Uani 1 1 d .
C14 C 0.7821(2) 0.73837(15) 1.10014(14) 0.0412(4) Uani 1 1 d .
H14 H 0.772680 0.682948 1.022127 0.049 Uiso 1 1 calc R
C6A C 0.2237(2) 0.55862(15) 0.24496(14) 0.0412(4) Uani 1 1 d .
C4A C 0.2790(2) 0.75402(17) 0.21827(16) 0.0469(4) Uani 1 1 d .
C10 C 0.8254(2) 0.94849(15) 1.24297(14) 0.0440(4) Uani 1 1 d .
H10 H 0.843363 1.035025 1.261204 0.053 Uiso 1 1 calc R
C5A C 0.2429(3) 0.62498(16) 0.17138(15) 0.0474(4) Uani 1 1 d .
C13 C 0.7658(2) 0.69246(16) 1.19035(16) 0.0450(4) Uani 1 1 d .
H13 H 0.742954 0.605966 1.171187 0.054 Uiso 1 1 calc R
C6 C 0.1885(2) 0.66461(17) 0.73242(15) 0.0494(4) Uani 1 1 d .
H6 H 0.066849 0.618982 0.690439 0.059 Uiso 1 1 calc R
C11 C 0.8117(3) 0.90052(17) 1.33244(15) 0.0489(4) Uani 1 1 d .
H11 H 0.822092 0.955876 1.410662 0.059 Uiso 1 1 calc R
C7 C 0.2293(2) 0.73929(17) 0.85432(15) 0.0473(4) Uani 1 1 d .
H7 H 0.137650 0.742358 0.894313 0.057 Uiso 1 1 calc R
C15 C 0.7735(3) 0.7210(2) 1.40736(19) 0.0631(5) Uani 1 1 d .
H15A H 0.673460 0.650697 1.373655 0.095 Uiso 1 1 calc GR
H15B H 0.747022 0.785710 1.472829 0.095 Uiso 1 1 calc GR
H15C H 0.894046 0.694284 1.438658 0.095 Uiso 1 1 calc GR
H1A H 0.258(4) 0.592(2) 0.525(2) 0.103(9) 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 115.9(15) . .
C1 N1 C9 123.63(11) . .
C1 N1 C2 106.64(11) . .
C2 N1 C9 128.19(12) . .
C5 N2 C6 118.44(14) . .
N1 C1 C3 142.41(13) . 2_777
C1 C1 N1 108.52(15) 2_777 .
C1 C1 C3 109.07(16) 2_777 2_777
C5 C4 C2 119.10(14) . .
C8 C4 C2 123.99(13) . .
C8 C4 C5 116.80(14) . .
C14 C9 N1 120.86(13) . .
C10 C9 N1 119.55(13) . .
C10 C9 C14 119.54(13) . .
N1 C2 C4 123.61(13) . .
C3 C2 N1 109.63(12) . .
C3 C2 C4 126.37(13) . .
C1 C3 H3 126.9 2_777 .
C2 C3 C1 106.14(13) . 2_777
C2 C3 H3 126.9 . .
O1A C1A C2A 125.36(14) . .
O1A C1A C6A 119.03(14) . .
C2A C1A C6A 115.59(14) . .
N2 C5 C4 123.71(15) . .
N2 C5 H5 118.1 . .
C4 C5 H5 118.1 . .
C4 C8 H8 120.1 . .
C7 C8 C4 119.77(15) . .
C7 C8 H8 120.1 . .
F3A C3A C2A 119.82(15) . .
F3A C3A C4A 120.03(15) . .
C4A C3A C2A 120.16(15) . .
C13 C12 C11 117.70(14) . .
C13 C12 C15 121.40(17) . .
C11 C12 C15 120.89(17) . .
F2A C2A C1A 119.46(14) . .
F2A C2A C3A 118.09(14) . .
C3A C2A C1A 122.45(15) . .
C9 C14 H14 120.1 . .
C9 C14 C13 119.74(15) . .
C13 C14 H14 120.1 . .
F6A C6A C1A 118.88(14) . .
F6A C6A C5A 118.88(14) . .
C5A C6A C1A 122.23(15) . .
F4A C4A C3A 120.45(16) . .
F4A C4A C5A 120.39(15) . .
C3A C4A C5A 119.16(15) . .
C9 C10 H10 120.1 . .
C9 C10 C11 119.77(15) . .
C11 C10 H10 120.1 . .
F5A C5A C6A 120.05(15) . .
F5A C5A C4A 119.56(15) . .
C4A C5A C6A 120.39(15) . .
C12 C13 C14 121.69(15) . .
C12 C13 H13 119.2 . .
C14 C13 H13 119.2 . .
N2 C6 H6 118.9 . .
N2 C6 C7 122.26(15) . .
C7 C6 H6 118.9 . .
C12 C11 C10 121.53(15) . .
C12 C11 H11 119.2 . .
C10 C11 H11 119.2 . .
C8 C7 H7 120.5 . .
C6 C7 C8 118.97(15) . .
C6 C7 H7 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
F6A C6A 1.3482(18) .
F2A C2A 1.3454(18) .
F3A C3A 1.3447(19) .
F4A C4A 1.3425(19) .
O1A C1A 1.3376(19) .
O1A H1A 0.99(3) .
F5A C5A 1.3456(19) .
N1 C1 1.3892(18) .
N1 C9 1.4319(18) .
N1 C2 1.4066(18) .
N2 C5 1.332(2) .
N2 C6 1.339(2) .
C1 C1 1.377(3) 2_777
C1 C3 1.408(2) 2_777
C4 C2 1.465(2) .
C4 C5 1.395(2) .
C4 C8 1.393(2) .
C9 C14 1.387(2) .
C9 C10 1.382(2) .
C2 C3 1.381(2) .
C3 H3 0.9300 .
C1A C2A 1.392(2) .
C1A C6A 1.393(2) .
C5 H5 0.9300 .
C8 H8 0.9300 .
C8 C7 1.384(2) .
C3A C2A 1.378(2) .
C3A C4A 1.368(2) .
C12 C13 1.380(2) .
C12 C11 1.388(2) .
C12 C15 1.516(2) .
C14 H14 0.9300 .
C14 C13 1.388(2) .
C6A C5A 1.375(2) .
C4A C5A 1.373(2) .
C10 H10 0.9300 .
C10 C11 1.389(2) .
C13 H13 0.9300 .
C6 H6 0.9300 .
C6 C7 1.380(2) .
C11 H11 0.9300 .
C7 H7 0.9300 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
