# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

data_yano090
_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)
;
_shelx_SHELXL_version_number      '2017/1'
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_id_orcid     ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          '2(C7 H3 F3 O2), C30 H24 N4'
_chemical_formula_sum             'C44 H30 F6 N4 O4'
_chemical_formula_weight          792.72
_chemical_melting_point           ?
_chemical_oxdiff_formula          'C H N O F'
_chemical_oxdiff_usercomment      'm-PyPP-F3 benzoic acid at 298 K'
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'

_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.
;
_space_group_crystal_system       'monoclinic'
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 1 21/c 1'
_space_group_name_Hall            '-P 2ybc'
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'

_cell_length_a                    5.8781(5)
_cell_length_b                    18.3134(19)
_cell_length_c                    17.3997(18)
_cell_angle_alpha                 90
_cell_angle_beta                  93.672(9)
_cell_angle_gamma                 90
_cell_volume                      1869.2(3)
_cell_formula_units_Z             2
_cell_measurement_reflns_used     984
_cell_measurement_temperature     298
_cell_measurement_theta_max       21.6480
_cell_measurement_theta_min       3.2020
_shelx_estimated_absorpt_T_max    ?
_shelx_estimated_absorpt_T_min    ?
_exptl_absorpt_coefficient_mu     0.112
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_correction_T_min   0.33907
_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_absorpt_special_details    ?
_exptl_crystal_colour             colourless
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.408
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_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
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.1041
_diffrn_reflns_av_unetI/netI      0.1305
_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        22
_diffrn_reflns_limit_k_min        -22
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_number             12241
_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          26.370
_diffrn_reflns_theta_min          2.515
_diffrn_ambient_temperature       298
_diffrn_detector                  'CCD plate'
_diffrn_detector_area_resol_mean  6.827
_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  100.00    --   30.00  54.00-180.00  193
  2  ω    -63.00 119.00   1.00  100.00    --   30.00  54.00 -60.00  182
;
_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       -0.0103221000
_diffrn_orient_matrix_UB_12       -0.0383276000
_diffrn_orient_matrix_UB_13       0.0044854000
_diffrn_orient_matrix_UB_21       0.0032615000
_diffrn_orient_matrix_UB_22       0.0043728000
_diffrn_orient_matrix_UB_23       0.0405716000
_diffrn_orient_matrix_UB_31       -0.1204044000
_diffrn_orient_matrix_UB_32       0.0034023000
_diffrn_orient_matrix_UB_33       -0.0019079000
_diffrn_oxdiff_ac3_digest_frames
;
01143cd81a10451942cb7b5b72de079fe000375756b
;
_diffrn_oxdiff_ac3_digest_hkl
;
010130d47e566593100f7fab04c14c59bc1a73
;
_diffrn_radiation_monochromator   graphite
_diffrn_radiation_probe           x-ray
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    'fine-focus sealed X-ray tube'
_diffrn_source_type               'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 1539
_reflns_number_total              3822
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric  1
_reflns_odcompleteness_theta      26.32
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression      'I > 2σ(I)'
_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)'
_refine_diff_density_max          0.168
_refine_diff_density_min          -0.247
_refine_diff_density_rms          0.049
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    0.992
_refine_ls_hydrogen_treatment     mixed
_refine_ls_matrix_type            full
_refine_ls_number_parameters      267
_refine_ls_number_reflns          3822
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1791
_refine_ls_R_factor_gt            0.0619
_refine_ls_restrained_S_all       0.992
_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)+(0.0350P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1164
_refine_ls_wR_factor_ref          0.1645
_refine_special_details           ?
_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), C10(H10), C15(H15), C8(H8), C11(H11), C14(H14), C6(H6),
 C2A(H2A), C7(H7), C6A(H6A)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens    mixed
_atom_sites_solution_primary      dual
_atom_sites_solution_secondary    ?
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
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 F001 F 1.3082(4) 0.45198(15) 0.73234(16) 0.0878(9) Uani 1 1 d . . . . .
 F002 F 1.1299(4) 0.53014(14) 0.61364(16) 0.0856(9) Uani 1 1 d . . . . .
 O1A O 0.4350(5) 0.29600(17) 0.59154(17) 0.0648(9) Uani 1 1 d . . . . .
 N1 N -0.2954(5) 0.05579(15) 0.54426(16) 0.0389(8) Uani 1 1 d . . . . .
 N2 N 0.0834(5) 0.25378(17) 0.49903(19) 0.0507(9) Uani 1 1 d . . . . .
 O2A O 0.4096(5) 0.39909(17) 0.52327(18) 0.0707(9) Uani 1 1 d . . . . .
 F007 F 1.0974(5) 0.33154(16) 0.77876(18) 0.1113(12) Uani 1 1 d . . . . .
 C1 C -0.4290(6) -0.0056(2) 0.5328(2) 0.0390(9) Uani 1 1 d . . . . .
 C3 C -0.5244(6) 0.07377(19) 0.4352(2) 0.0414(10) Uani 1 1 d . . . . .
 H3 H -0.593403 0.094227 0.390683 0.050 Uiso 1 1 calc R . . . .
 C2 C -0.3539(6) 0.1044(2) 0.4838(2) 0.0396(9) Uani 1 1 d . . . . .
 C4 C -0.2381(6) 0.1740(2) 0.4745(2) 0.0395(9) Uani 1 1 d . . . . .
 C9 C -0.1503(6) 0.0700(2) 0.6114(2) 0.0408(9) Uani 1 1 d . . . . .
 C5 C -0.0171(6) 0.1891(2) 0.5045(2) 0.0462(10) Uani 1 1 d . . . . .
 H5 H 0.064540 0.151672 0.529744 0.055 Uiso 1 1 calc R . . . .
 C10 C 0.0404(6) 0.0267(2) 0.6266(2) 0.0474(10) Uani 1 1 d . . . . .
 H10 H 0.066459 -0.013396 0.595583 0.057 Uiso 1 1 calc R . . . .
 C15 C -0.1934(6) 0.1268(2) 0.6590(2) 0.0502(11) Uani 1 1 d . . . . .
 H15 H -0.325118 0.154489 0.650354 0.060 Uiso 1 1 calc R . . . .
 C8 C -0.3470(7) 0.2299(2) 0.4319(2) 0.0505(11) Uani 1 1 d . . . . .
 H8 H -0.491625 0.222436 0.408292 0.061 Uiso 1 1 calc R . . . .
 C1A C 0.7168(6) 0.3857(2) 0.6178(2) 0.0517(11) Uani 1 1 d . . . . .
 C12 C 0.1563(6) 0.1022(2) 0.7351(2) 0.0506(11) Uani 1 1 d . . . . .
 C11 C 0.1916(6) 0.0435(2) 0.6881(2) 0.0521(11) Uani 1 1 d . . . . .
 H11 H 0.319851 0.014416 0.697968 0.063 Uiso 1 1 calc R . . . .
 C14 C -0.0395(7) 0.1430(2) 0.7207(2) 0.0557(12) Uani 1 1 d . . . . .
 H14 H -0.068858 0.182034 0.752843 0.067 Uiso 1 1 calc R . . . .
 C3A C 1.0188(7) 0.4696(2) 0.6337(3) 0.0569(12) Uani 1 1 d . . . . .
 C6 C -0.0271(7) 0.3070(2) 0.4603(2) 0.0557(11) Uani 1 1 d . . . . .
 H6 H 0.041261 0.352556 0.457212 0.067 Uiso 1 1 calc R . . . .
 C7A C 0.5049(7) 0.3624(2) 0.5724(3) 0.0564(12) Uani 1 1 d . . . . .
 C4A C 1.1116(7) 0.4301(3) 0.6952(3) 0.0614(12) Uani 1 1 d . . . . .
 C2A C 0.8207(7) 0.4491(2) 0.5953(2) 0.0555(11) Uani 1 1 d . . . . .
 H2A H 0.756655 0.477003 0.554823 0.067 Uiso 1 1 calc R . . . .
 C7 C -0.2403(7) 0.2961(2) 0.4248(2) 0.0580(12) Uani 1 1 d . . . . .
 H7 H -0.311779 0.333390 0.396165 0.070 Uiso 1 1 calc R . . . .
 C6A C 0.8067(7) 0.3453(2) 0.6794(3) 0.0640(13) Uani 1 1 d . . . . .
 H6A H 0.734694 0.303043 0.694742 0.077 Uiso 1 1 calc R . . . .
 C5A C 1.0045(8) 0.3689(2) 0.7174(3) 0.0664(13) Uani 1 1 d . . . . .
 C13 C 0.3281(7) 0.1224(3) 0.8000(2) 0.0732(15) Uani 1 1 d . . . . .
 H13A H 0.268048 0.110188 0.848415 0.110 Uiso 1 1 calc GR . . . .
 H13B H 0.358082 0.173892 0.798394 0.110 Uiso 1 1 calc GR . . . .
 H13C H 0.467079 0.095960 0.794490 0.110 Uiso 1 1 calc GR . . . .
 H1A H 0.296(9) 0.278(3) 0.555(3) 0.118(19) Uiso 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 F001 C4A 1.348(4) . ?
 F002 C3A 1.344(4) . ?
 O1A C7A 1.333(5) . ?
 O1A H1A 1.06(5) . ?
 N1 C1 1.378(4) . ?
 N1 C2 1.405(4) . ?
 N1 C9 1.426(4) . ?
 N2 C5 1.331(4) . ?
 N2 C6 1.330(4) . ?
 O2A C7A 1.197(5) . ?
 F007 C5A 1.353(5) . ?
 C1 C1 1.385(6) 3_456 ?
 C1 C3 1.401(5) 3_456 ?
 C3 H3 0.9300 . ?
 C3 C2 1.388(4) . ?
 C2 C4 1.459(5) . ?
 C4 C5 1.396(4) . ?
 C4 C8 1.395(5) . ?
 C9 C10 1.384(5) . ?
 C9 C15 1.364(5) . ?
 C5 H5 0.9300 . ?
 C10 H10 0.9300 . ?
 C10 C11 1.381(5) . ?
 C15 H15 0.9300 . ?
 C15 C14 1.391(5) . ?
 C8 H8 0.9300 . ?
 C8 C7 1.373(5) . ?
 C1A C7A 1.494(5) . ?
 C1A C2A 1.380(5) . ?
 C1A C6A 1.378(5) . ?
 C12 C11 1.374(5) . ?
 C12 C14 1.382(5) . ?
 C12 C13 1.512(5) . ?
 C11 H11 0.9300 . ?
 C14 H14 0.9300 . ?
 C3A C4A 1.375(6) . ?
 C3A C2A 1.358(5) . ?
 C6 H6 0.9300 . ?
 C6 C7 1.375(5) . ?
 C4A C5A 1.354(6) . ?
 C2A H2A 0.9300 . ?
 C7 H7 0.9300 . ?
 C6A H6A 0.9300 . ?
 C6A C5A 1.370(5) . ?
 C13 H13A 0.9600 . ?
 C13 H13B 0.9600 . ?
 C13 H13C 0.9600 . ?

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
  _geom_angle_publ_flag
 C7A O1A H1A 112(3) . . ?
 C1 N1 C2 107.4(3) . . ?
 C1 N1 C9 125.0(3) . . ?
 C2 N1 C9 127.1(3) . . ?
 C6 N2 C5 118.9(3) . . ?
 N1 C1 C1 107.8(4) . 3_456 ?
 N1 C1 C3 142.5(3) . 3_456 ?
 C1 C1 C3 109.6(4) 3_456 3_456 ?
 C1 C3 H3 127.1 3_456 . ?
 C2 C3 C1 105.7(3) . 3_456 ?
 C2 C3 H3 127.1 . . ?
 N1 C2 C4 123.0(3) . . ?
 C3 C2 N1 109.4(3) . . ?
 C3 C2 C4 127.6(3) . . ?
 C5 C4 C2 124.1(3) . . ?
 C8 C4 C2 119.9(3) . . ?
 C8 C4 C5 116.0(3) . . ?
 C10 C9 N1 119.1(3) . . ?
 C15 C9 N1 120.8(3) . . ?
 C15 C9 C10 120.0(3) . . ?
 N2 C5 C4 123.7(3) . . ?
 N2 C5 H5 118.1 . . ?
 C4 C5 H5 118.1 . . ?
 C9 C10 H10 120.2 . . ?
 C11 C10 C9 119.6(4) . . ?
 C11 C10 H10 120.2 . . ?
 C9 C15 H15 120.2 . . ?
 C9 C15 C14 119.7(4) . . ?
 C14 C15 H15 120.2 . . ?
 C4 C8 H8 120.1 . . ?
 C7 C8 C4 119.9(3) . . ?
 C7 C8 H8 120.1 . . ?
 C2A C1A C7A 117.3(4) . . ?
 C6A C1A C7A 121.6(4) . . ?
 C6A C1A C2A 121.2(4) . . ?
 C11 C12 C14 118.1(4) . . ?
 C11 C12 C13 121.1(4) . . ?
 C14 C12 C13 120.7(4) . . ?
 C10 C11 H11 119.3 . . ?
 C12 C11 C10 121.4(4) . . ?
 C12 C11 H11 119.3 . . ?
 C15 C14 H14 119.4 . . ?
 C12 C14 C15 121.1(4) . . ?
 C12 C14 H14 119.4 . . ?
 F002 C3A C4A 117.5(4) . . ?
 F002 C3A C2A 121.0(4) . . ?
 C2A C3A C4A 121.5(4) . . ?
 N2 C6 H6 119.2 . . ?
 N2 C6 C7 121.6(4) . . ?
 C7 C6 H6 119.2 . . ?
 O1A C7A C1A 112.8(4) . . ?
 O2A C7A O1A 123.6(4) . . ?
 O2A C7A C1A 123.6(4) . . ?
 F001 C4A C3A 120.1(4) . . ?
 F001 C4A C5A 120.6(4) . . ?
 C5A C4A C3A 119.3(4) . . ?
 C1A C2A H2A 120.9 . . ?
 C3A C2A C1A 118.3(4) . . ?
 C3A C2A H2A 120.9 . . ?
 C8 C7 C6 119.7(4) . . ?
 C8 C7 H7 120.1 . . ?
 C6 C7 H7 120.1 . . ?
 C1A C6A H6A 120.7 . . ?
 C5A C6A C1A 118.5(4) . . ?
 C5A C6A H6A 120.7 . . ?
 F007 C5A C4A 118.2(4) . . ?
 F007 C5A C6A 120.6(4) . . ?
 C4A C5A C6A 121.2(4) . . ?
 C12 C13 H13A 109.5 . . ?
 C12 C13 H13B 109.5 . . ?
 C12 C13 H13C 109.5 . . ?
 H13A C13 H13B 109.5 . . ?
 H13A C13 H13C 109.5 . . ?
 H13B C13 H13C 109.5 . . ?

_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 2.232
_oxdiff_exptl_absorpt_empirical_full_min 0.758
