Controlling the canonical/zwitterionic balance through intramolecular proton transfer: a strategy for vapochromism
Pascal, Simon; Lavaud, Lucien; Azarias, Cloé; Canard, Gabriel; Giorgi, Michel; Jacquemin, Denis; Siri, Olivier; Materials Chemistry Frontiers 2 (2018) 1618–; doi:10.1039/C8QM00171E

data_1554221
_publ_section_title
;
 Controlling the canonical/zwitterionic balance through intramolecular
 proton transfer: a strategy for vapochromism
;
_journal_issue                   9
_journal_name_full               'Materials Chemistry Frontiers'
_journal_page_first              1618
_journal_paper_doi               10.1039/C8QM00171E
_journal_volume                  2
_journal_year                    2018
_chemical_formula_moiety         'C22 H12 F12 N4'
_chemical_formula_sum            'C22 H12 F12 N4'
_chemical_formula_weight         560.36
_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             2017-10-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-22 deposited with the CCDC.
2018-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.4090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.8769(2)
_cell_length_b                   17.4704(2)
_cell_length_c                   16.9020(2)
_cell_measurement_reflns_used    15921
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.8250
_cell_measurement_theta_min      3.7900
_cell_volume                     4595.57(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_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      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -107.00 -35.00   1.00    1.00    --  -17.77-178.00 -60.00   72
  2  \w    -92.00   3.00   1.00    1.00    --  -17.77 -38.00 120.00   95
  3  \w    -91.00 -36.00   1.00    1.00    --  -17.77 178.00 120.00   55
  4  \w    -91.00   4.00   1.00    1.00    --  -17.77 -57.00  60.00   95
  5  \w    -15.00  31.00   1.00    1.00    --   17.77  77.00 -60.00   46
  6  \w     62.00 104.00   1.00    1.00    --   17.77 178.00  30.00   42
  7  \w     15.00  63.00   1.00    1.00    --   17.77  77.00   0.00   48
  8  \w     39.00  94.00   1.00    1.00    --   17.77  77.00 -60.00   55
  9  \w    113.00 146.00   1.00   30.00    --  101.41 125.00 -60.00   33
 10  \w     25.00  76.00   1.00   30.00    --  101.41 -30.00 150.00   51
 11  \w     30.00 109.00   1.00   30.00    --  101.41 -94.00  60.00   79
 12  \w     59.00 120.00   1.00   30.00    --  101.41 -77.00 120.00   61
 13  \w     77.00 173.00   1.00   30.00    --  101.41  45.00  60.00   96
 14  \w     35.00 123.00   1.00   30.00    --  101.41 -45.00  30.00   88
 15  \w     72.00 104.00   1.00   30.00    --  101.41 -94.00 -30.00   32
 16  \w     95.00 173.00   1.00   30.00    --  101.41  45.00-180.00   78
 17  \w     30.00 114.00   1.00   30.00    --  101.41 -61.00 -90.00   84
 18  \w    112.00 139.00   1.00   30.00    --  101.41 125.00  60.00   27
 19  \w     28.00 121.00   1.00   30.00    --  101.41-125.00 -60.00   93
 20  \w     60.00 178.00   1.00   30.00    --  101.41  15.00 -30.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0486199000
_diffrn_orient_matrix_UB_12      -0.0583737000
_diffrn_orient_matrix_UB_13      -0.0425209000
_diffrn_orient_matrix_UB_21      -0.0266056000
_diffrn_orient_matrix_UB_22      -0.0646701000
_diffrn_orient_matrix_UB_23      0.0519936000
_diffrn_orient_matrix_UB_31      -0.0819969000
_diffrn_orient_matrix_UB_32      -0.0136570000
_diffrn_orient_matrix_UB_33      -0.0643337000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33093
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.952
_diffrn_reflns_theta_min         3.677
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.506
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.18b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_description       plate
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     850
_refine_ls_number_reflns         8752
_refine_ls_number_restraints     261
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0815
_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/[\s^2^(Fo^2^)+(0.1655P)^2^+1.8508P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2315
_refine_ls_wR_factor_ref         0.2431
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7519
_reflns_number_total             8752
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qm00171e2.cif
_cod_data_source_block           lnl294
_cod_database_code               1554221
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c22 h12 n12 o4'
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.520
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F26) = Uanis(F22)
Uanis(F19) = Uanis(F18)
Uanis(F27) = Uanis(F24)
Uanis(F25) = Uanis(F22)
3. Rigid body (RIGU) restrains
 F40, F41, F42, C43, F43, F44, F45
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F35, F34, F36, C44, F39, F38, F37
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F24, F23, C36, F22, F26, F25, F27
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F29, F30, F28, C35, F31, F32, F33
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F17, F18, F16, C22, F21, F20, F19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F11, F10, C21, F12, F14, F15, F13
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F4, C14, F5, F6, F7, F9, F8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: F4(0.8) F5(0.8) F6(0.8) F7(0.2) F8(0.2) F9(0.2) F10(0.8) F11(0.8)
 F12(0.8) F13(0.2) F14(0.2) F15(0.2) F16(0.8) F17(0.8) F18(0.8) F19(0.2)
 F20(0.2) F21(0.2) F22(0.8) F23(0.8) F24(0.8) F25(0.2) F26(0.2) F27(0.2)
 F28(0.8) F29(0.8) F30(0.8) F31(0.2) F32(0.2) F33(0.2) F34(0.8) F35(0.8)
 F36(0.8) F37(0.2) F38(0.2) F39(0.2) F40(0.8) F41(0.8) F42(0.8) F43(0.2)
 F44(0.2) F45(0.2)
5.a Riding coordinates:
 N3(H3), N8(H8)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C5(H5), C8(H8A), C10(H10), C12(H12), C16(H16), C18(H18),
 C20(H20), N6(H6), C24(H24), C27(H27), C30(H30), C32(H32), C34(H34), C38(H38),
 C40(H40), C42(H42)
5.c X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N7(H7A,H7B)
;
_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 1.687
_oxdiff_exptl_absorpt_empirical_full_min 0.429