#------------------------------------------------------------------------------
#$Date: 2019-11-24 17:02:53 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238703 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/78/7237885.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_7237885
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 H3 F3 O2), C30 H24 N4'
_chemical_formula_sum            'C44 H30 F6 N4 O4'
_chemical_formula_weight         792.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-30
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.591(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9103(5)
_cell_length_b                   18.358(2)
_cell_length_c                   17.0558(19)
_cell_measurement_reflns_used    874
_cell_measurement_temperature    123
_cell_measurement_theta_max      22.6360
_cell_measurement_theta_min      3.2210
_cell_volume                     1848.7(3)
_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   96.20    --   30.00  54.00-180.00  193
  2  ω    -72.00 112.00   1.00   96.20    --   30.00  54.00  60.00  184
;
_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      -0.0150524000
_diffrn_orient_matrix_UB_12      -0.0379924000
_diffrn_orient_matrix_UB_13      0.0050796000
_diffrn_orient_matrix_UB_21      -0.0001364000
_diffrn_orient_matrix_UB_22      0.0050079000
_diffrn_orient_matrix_UB_23      0.0412525000
_diffrn_orient_matrix_UB_31      -0.1192166000
_diffrn_orient_matrix_UB_32      0.0047467000
_diffrn_orient_matrix_UB_33      -0.0025601000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1341
_diffrn_reflns_av_unetI/netI     0.1633
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11892
_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         26.371
_diffrn_reflns_theta_min         2.520
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63922
_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    1.424
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1866
_refine_ls_R_factor_gt           0.0732
_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)+(0.0640P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.2228
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1613
_reflns_number_total             3775
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9tc02524c12.cif
_cod_data_source_block           yano089
_cod_database_code               7237885
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N O F Cl'
_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
;
013fb9b8fe0356bbd23126c83485c7aab500377b815
;
_diffrn_oxdiff_ac3_digest_hkl
;
01f1b1069274f1751882b2e188a7951c022cda
;
_reflns_odcompleteness_completeness 99.87
_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), C10(H10), C5(H5), C8(H8), C11(H11), C14(H14), C2A(H2A), C6(H6),
 C6A(H6A), C7(H7), C13(H13)
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 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.794
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
F3A F -0.1292(5) 0.46909(15) 0.38785(17) 0.0463(8) Uani 1 1 d .
F4A F -0.3083(5) 0.54895(16) 0.26718(17) 0.0472(8) Uani 1 1 d .
F5A F -0.0965(5) 0.67026(17) 0.21816(18) 0.0566(9) Uani 1 1 d .
O1A O 0.5711(6) 0.70430(18) 0.4049(2) 0.0380(9) Uani 1 1 d .
O2A O 0.5961(5) 0.59953(18) 0.4747(2) 0.0387(9) Uani 1 1 d .
N1 N 1.2962(6) 0.9442(2) 0.4547(2) 0.0264(9) Uani 1 1 d .
N2 N 0.9162(6) 0.7444(2) 0.4996(2) 0.0304(9) Uani 1 1 d .
C1 C 1.4300(7) 1.0059(2) 0.4666(2) 0.0254(10) Uani 1 1 d .
C4 C 1.2378(7) 0.8244(2) 0.5254(2) 0.0251(10) Uani 1 1 d .
C9 C 1.1494(7) 0.9306(2) 0.3870(3) 0.0272(11) Uani 1 1 d .
C3 C 1.5234(7) 0.9252(2) 0.5647(3) 0.0271(11) Uani 1 1 d .
H3 H 1.592054 0.904294 0.609391 0.033 Uiso 1 1 calc R
C2 C 1.3542(7) 0.8945(2) 0.5158(2) 0.0255(10) Uani 1 1 d .
C10 C 0.9615(8) 0.9747(2) 0.3732(3) 0.0314(11) Uani 1 1 d .
H10 H 0.938677 1.015050 0.404891 0.038 Uiso 1 1 calc R
C5 C 1.0169(8) 0.8102(3) 0.4955(3) 0.0286(11) Uani 1 1 d .
H5 H 0.935708 0.848180 0.471632 0.034 Uiso 1 1 calc R
C7A C 0.4987(8) 0.6374(3) 0.4248(3) 0.0333(12) Uani 1 1 d .
C1A C 0.2877(8) 0.6143(2) 0.3796(3) 0.0298(11) Uani 1 1 d .
C8 C 1.3481(8) 0.7673(3) 0.5667(3) 0.0318(11) Uani 1 1 d .
H8 H 1.492744 0.774123 0.589290 0.038 Uiso 1 1 calc R
C11 C 0.8069(8) 0.9584(3) 0.3116(3) 0.0342(12) Uani 1 1 d .
H11 H 0.680204 0.987743 0.302559 0.041 Uiso 1 1 calc R
C14 C 1.1909(8) 0.8722(3) 0.3380(3) 0.0322(12) Uani 1 1 d .
H14 H 1.321208 0.844286 0.345982 0.039 Uiso 1 1 calc R
C2A C 0.1820(7) 0.5505(2) 0.4039(3) 0.0313(11) Uani 1 1 d .
H2A H 0.244827 0.522590 0.444887 0.038 Uiso 1 1 calc R
C12 C 0.8407(8) 0.8979(3) 0.2632(3) 0.0330(12) Uani 1 1 d .
C3A C -0.0161(8) 0.5304(3) 0.3656(3) 0.0335(12) Uani 1 1 d .
C6 C 1.0298(8) 0.6910(3) 0.5380(3) 0.0328(12) Uani 1 1 d .
H6 H 0.963061 0.645221 0.540501 0.039 Uiso 1 1 calc R
C4A C -0.1120(8) 0.5703(3) 0.3040(3) 0.0336(12) Uani 1 1 d .
C6A C 0.1958(8) 0.6551(3) 0.3174(3) 0.0348(12) Uani 1 1 d .
H6A H 0.266539 0.697511 0.301559 0.042 Uiso 1 1 calc R
C7 C 1.2400(8) 0.7011(3) 0.5736(3) 0.0344(12) Uani 1 1 d .
H7 H 1.309468 0.663532 0.602186 0.041 Uiso 1 1 calc R
C5A C -0.0002(8) 0.6318(3) 0.2799(3) 0.0361(12) Uani 1 1 d .
C13 C 1.0345(8) 0.8560(3) 0.2767(3) 0.0365(12) Uani 1 1 d .
H13 H 1.060373 0.816386 0.244233 0.044 Uiso 1 1 calc R
C15 C 0.6677(8) 0.8780(3) 0.1987(3) 0.0435(14) Uani 1 1 d .
H15A H 0.526927 0.901989 0.207766 0.065 Uiso 1 1 calc GR
H15B H 0.645073 0.826243 0.198285 0.065 Uiso 1 1 calc GR
H15C H 0.721364 0.893213 0.148937 0.065 Uiso 1 1 calc GR
H1A H 0.693(8) 0.719(2) 0.442(3) 0.036(14) 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
C7A O1A H1A 109(3) . .
C1 N1 C9 125.3(4) . .
C1 N1 C2 107.5(3) . .
C2 N1 C9 126.8(4) . .
C6 N2 C5 117.8(4) . .
N1 C1 C1 107.7(5) . 3_876
N1 C1 C3 142.9(4) . 3_876
C1 C1 C3 109.4(5) 3_876 3_876
C5 C4 C2 123.6(4) . .
C5 C4 C8 116.5(4) . .
C8 C4 C2 119.9(4) . .
C10 C9 N1 119.1(4) . .
C10 C9 C14 120.8(4) . .
C14 C9 N1 120.1(4) . .
C1 C3 H3 126.7 3_876 .
C2 C3 C1 106.6(4) . 3_876
C2 C3 H3 126.7 . .
N1 C2 C4 123.1(4) . .
C3 C2 N1 108.9(4) . .
C3 C2 C4 127.9(4) . .
C9 C10 H10 120.2 . .
C9 C10 C11 119.7(4) . .
C11 C10 H10 120.2 . .
N2 C5 C4 123.5(4) . .
N2 C5 H5 118.2 . .
C4 C5 H5 118.2 . .
O1A C7A C1A 113.2(4) . .
O2A C7A O1A 123.2(5) . .
O2A C7A C1A 123.6(5) . .
C2A C1A C7A 117.2(4) . .
C6A C1A C7A 121.9(4) . .
C6A C1A C2A 120.9(4) . .
C4 C8 H8 120.3 . .
C7 C8 C4 119.5(4) . .
C7 C8 H8 120.3 . .
C10 C11 H11 119.7 . .
C10 C11 C12 120.5(4) . .
C12 C11 H11 119.7 . .
C9 C14 H14 120.4 . .
C9 C14 C13 119.1(4) . .
C13 C14 H14 120.4 . .
C1A C2A H2A 121.0 . .
C3A C2A C1A 118.0(5) . .
C3A C2A H2A 121.0 . .
C11 C12 C15 120.7(4) . .
C13 C12 C11 118.7(4) . .
C13 C12 C15 120.7(4) . .
F3A C3A C4A 117.2(4) . .
C2A C3A F3A 120.5(4) . .
C2A C3A C4A 122.3(5) . .
N2 C6 H6 118.6 . .
N2 C6 C7 122.7(4) . .
C7 C6 H6 118.6 . .
F4A C4A C3A 120.9(4) . .
F4A C4A C5A 120.7(4) . .
C5A C4A C3A 118.4(4) . .
C1A C6A H6A 120.6 . .
C5A C6A C1A 118.9(5) . .
C5A C6A H6A 120.6 . .
C8 C7 H7 120.1 . .
C6 C7 C8 119.7(4) . .
C6 C7 H7 120.1 . .
F5A C5A C4A 117.6(4) . .
C6A C5A F5A 120.8(5) . .
C6A C5A C4A 121.6(5) . .
C14 C13 H13 119.4 . .
C12 C13 C14 121.1(5) . .
C12 C13 H13 119.4 . .
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
F3A C3A 1.372(5) .
F4A C4A 1.353(5) .
F5A C5A 1.370(5) .
O1A C7A 1.349(6) .
O1A H1A 0.97(5) .
O2A C7A 1.222(5) .
N1 C1 1.392(5) .
N1 C9 1.434(6) .
N1 C2 1.416(5) .
N2 C5 1.350(5) .
N2 C6 1.342(5) .
C1 C1 1.395(8) 3_876
C1 C3 1.404(6) 3_876
C4 C2 1.472(6) .
C4 C5 1.404(6) .
C4 C8 1.406(6) .
C9 C10 1.386(6) .
C9 C14 1.387(6) .
C3 H3 0.9300 .
C3 C2 1.392(6) .
C10 H10 0.9300 .
C10 C11 1.393(6) .
C5 H5 0.9300 .
C7A C1A 1.497(6) .
C1A C2A 1.400(6) .
C1A C6A 1.388(6) .
C8 H8 0.9300 .
C8 C7 1.381(6) .
C11 H11 0.9300 .
C11 C12 1.402(6) .
C14 H14 0.9300 .
C14 C13 1.398(6) .
C2A H2A 0.9300 .
C2A C3A 1.365(6) .
C12 C13 1.391(7) .
C12 C15 1.513(6) .
C3A C4A 1.381(7) .
C6 H6 0.9300 .
C6 C7 1.371(6) .
C4A C5A 1.379(7) .
C6A H6A 0.9300 .
C6A C5A 1.367(6) .
C7 H7 0.9300 .
C13 H13 0.9300 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
