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_1554222
_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         'C34 H42 F2 N8 O8'
_chemical_formula_sum            'C34 H42 F2 N8 O8'
_chemical_formula_weight         728.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-03-22 deposited with the CCDC.
2018-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.648(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0537(2)
_cell_length_b                   17.8869(4)
_cell_length_c                   22.6505(4)
_cell_measurement_reflns_used    11633
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.5670
_cell_measurement_theta_min      4.6060
_cell_volume                     3664.16(13)
_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 1.000
_diffrn_measured_fraction_theta_max 0.987
_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    -49.00   9.00   1.00    5.00    --  -17.77 -57.00-180.00   58
  2  \w   -105.00 -66.00   1.00    5.00    --  -17.77 178.00 -60.00   39
  3  \w    -55.00 -28.00   1.00    5.00    --  -17.77 -57.00 -60.00   27
  4  \w    -98.00 -38.00   1.00    5.00    --  -17.77 -19.00-180.00   60
  5  \w    -31.00   7.00   1.00    5.00    --  -17.77 -38.00 -60.00   38
  6  \w   -105.00 -35.00   1.00    5.00    --  -17.77 178.00-120.00   70
  7  \w    -78.00 -52.00   1.00    5.00    --  -17.77 -57.00 -90.00   26
  8  \w    -35.00  -9.00   1.00    5.00    --  -17.77 -57.00 120.00   26
  9  \w    -70.00 -44.00   1.00    5.00    --  -17.77 -38.00 -90.00   26
 10  \w    -22.00  18.00   1.00    5.00    --  -17.77 -19.00-180.00   40
 11  \w    -91.00   5.00   1.00    5.00    --  -17.77 -38.00  90.00   96
 12  \w     73.00  98.00   1.00    5.00    --   17.77  19.00  90.00   25
 13  \w     62.00  87.00   1.00    5.00    --   17.77-178.00  90.00   25
 14  \w     10.00  92.00   1.00    5.00    --   17.77  38.00   0.00   82
 15  \w     39.00  66.00   1.00    5.00    --   17.77  19.00  90.00   27
 16  \w     20.00  45.00   1.00    5.00    --   17.77  77.00 -60.00   25
 17  \w     70.00 153.00   1.00   30.00    --  101.41  77.00-150.00   83
 18  \w     76.00 102.00   1.00   30.00    --  101.41  45.00  30.00   26
 19  \w     72.00  98.00   1.00   30.00    --  101.41  61.00-120.00   26
 20  \w     76.00 102.00   1.00   30.00    --  101.41  45.00 -30.00   26
 21  \w    147.00 172.00   1.00   30.00    --  101.41  61.00 -90.00   25
 22  \w    126.00 157.00   1.00   30.00    --  101.41  77.00   0.00   31
 23  \w     69.00  96.00   1.00   30.00    --  101.41  77.00   0.00   27
 24  \w     72.00  98.00   1.00   30.00    --  101.41  61.00 -90.00   26
 25  \w     69.00  95.00   1.00   30.00    --  101.41  77.00-120.00   26
 26  \w     72.00  98.00   1.00   30.00    --  101.41  61.00 -30.00   26
 27  \w     46.00  72.00   1.00   30.00    --  101.41 -94.00-120.00   26
 28  \w     84.00 109.00   1.00   30.00    --  101.41 -94.00-120.00   25
 29  \w     72.00  98.00   1.00   30.00    --  101.41  61.00   0.00   26
 30  \w     77.00 102.00   1.00   30.00    --  101.41  45.00 -60.00   25
 31  \w     69.00  95.00   1.00   30.00    --  101.41  77.00 -60.00   26
 32  \w     74.00 108.00   1.00   30.00    --  101.41  30.00 -30.00   34
 33  \w     69.00  95.00   1.00   30.00    --  101.41  77.00 -90.00   26
 34  \w    144.00 170.00   1.00   30.00    --  101.41  61.00 -60.00   26
 35  \w    107.00 177.00   1.00   30.00    --  101.41  77.00 -30.00   70
 36  \w     73.00 100.00   1.00   30.00    --  101.41  61.00  30.00   27
 37  \w     74.00 177.00   1.00   30.00    --  101.41  30.00 -90.00  103
 38  \w     73.00 100.00   1.00   30.00    --  101.41  30.00 -60.00   27
 39  \w     73.00 100.00   1.00   30.00    --  101.41  30.00   0.00   27
 40  \w     77.00 102.00   1.00   30.00    --  101.41  45.00 -90.00   25
 41  \w     77.00 102.00   1.00   30.00    --  101.41  45.00   0.00   25
 42  \w     69.00 100.00   1.00   30.00    --  101.41  77.00 -30.00   31
 43  \w     72.00  98.00   1.00   30.00    --  101.41  61.00 -60.00   26
 44  \w     29.00 130.00   1.00   30.00    --  101.41 -61.00  60.00  101
 45  \w     70.00  95.00   1.00   30.00    --  101.41  77.00  30.00   25
 46  \w     51.00  94.00   1.00   30.00    --  101.41  15.00  30.00   43
 47  \w     25.00 134.00   1.00   30.00    --  101.41 -77.00-120.00  109
;
_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      -0.0162381000
_diffrn_orient_matrix_UB_12      -0.0145407000
_diffrn_orient_matrix_UB_13      -0.0670322000
_diffrn_orient_matrix_UB_21      0.1674178000
_diffrn_orient_matrix_UB_22      0.0122273000
_diffrn_orient_matrix_UB_23      -0.0050707000
_diffrn_orient_matrix_UB_31      0.0271111000
_diffrn_orient_matrix_UB_32      -0.0839783000
_diffrn_orient_matrix_UB_33      0.0108557000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            36478
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.155
_diffrn_reflns_theta_min         3.907
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.862
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81420
_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            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         7011
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0727
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1125P)^2^+2.4762P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2032
_refine_ls_wR_factor_ref         0.2245
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5254
_reflns_number_total             7011
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qm00171e2.cif
_cod_data_source_block           spo77
_cod_database_code               1554222
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c34 h40 f2 n8 o8'
_diffrn_oxdiff_ac3_digest_frames
;
0150175dc1f029244ab48b827e5605fcb00002821ea
;
_diffrn_oxdiff_ac3_digest_hkl
;
0146668b883e479d37170ebbe83e397732f6f4
;
_reflns_odcompleteness_completeness 99.95
_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 C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C32-C35
 1.54 with sigma of 0.02
 C32-C33
 1.54 with sigma of 0.02
 C35-C36
 1.54 with sigma of 0.02
 C33-C34
 1.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C31 \\sim C32 \\sim C35: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C31 \\sim C32 \\sim C33: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C32 \\sim C35 \\sim C36: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C32 \\sim C33 \\sim C34: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
Uanis(C35) = Uanis(C33)
Uanis(C36) = Uanis(C34)
4. Others
 Fixed Sof: H32A(0.5) H32B(0.5) H32C(0.5) H32D(0.5) C33(0.5) H33A(0.5)
 H33B(0.5) C34(0.5) H34A(0.5) H34B(0.5) H34C(0.5) C35(0.5) H35A(0.5) H35B(0.5)
 C36(0.5) H36A(0.5) H36B(0.5) H36C(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,
 H17B), C18(H18A,H18B), C19(H19A,H19B), C27(H27A,H27B), C28(H28A,H28B),
 C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C32(H32C,H32D),
  C33(H33A,H33B), C35(H35A,H35B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), C3(H3), C6(H6), C9(H9), C12(H12), C22(H22), C25(H25)
5.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C34(H34A,H34B,H34C), C36(H36A,H36B,H36C)
;
_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 1.528
_oxdiff_exptl_absorpt_empirical_full_min 0.573