Positively and negatively charged NHN hydrogen bonds in one molecule: synergistic strengthening effect, superbasicity and acetonitrile capture
Vlasenko, Marina P.; Ozeryanskii, Valery A.; Pozharskii, Alexander F.; Khoroshilova, Olesya V.; New Journal of Chemistry 43 (2019) 7557–; doi:10.1039/C9NJ00965E

data_7058322
_publ_section_title
;
 Positively and negatively charged NHN hydrogen bonds in one molecule:
 synergistic strengthening effect, superbasicity and acetonitrile capture
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7557
_journal_paper_doi               10.1039/C9NJ00965E
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C28 H33 N4 O4 S2, B F4'
_chemical_formula_sum            'C28 H33 B F4 N4 O4 S2'
_chemical_formula_weight         640.51
_chemical_melting_point          'decomp. above 215 deg.C'
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-21 deposited with the CCDC.    2019-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.1510(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.09480(10)
_cell_length_b                   12.45500(10)
_cell_length_c                   22.3878(2)
_cell_measurement_reflns_used    17650
_cell_measurement_temperature    100(5)
_cell_measurement_theta_max      72.6550
_cell_measurement_theta_min      3.9630
_cell_volume                     3069.61(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (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_environment      N~2~
_diffrn_ambient_temperature      100(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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     18.00  66.00   0.50    0.28    --   38.95 -83.00-130.00   96
  2  \w    -28.00   9.00   0.50    0.28    --   38.95 -83.00-130.00   74
  3  \w     72.00 112.00   0.50    1.11    --  104.92 -83.00-130.00   80
  4  \w     86.00 156.00   0.50    1.11    --  104.92  83.00  -9.00  140
  5  \w    -49.00 -20.00   0.50    0.28    --  -38.95 -21.00  30.00   58
  6  \w    -56.00 -13.00   0.50    0.28    --  -38.95  43.00 -30.00   86
  7  \w    -51.00 -18.00   0.50    0.28    --  -38.95  83.00  -9.00   66
  8  \w     -8.00  29.00   0.50    0.28    --  -38.95  83.00  -9.00   74
  9  \w   -100.00 -57.00   0.50    0.28    --  -38.95 -21.00  30.00   86
 10  \w     -8.00  27.00   0.50    0.28    --  -38.95  43.00 -30.00   70
 11  \w     22.00  61.00   0.50    0.28    --   38.95  21.00 -30.00   78
 12  \w     26.00  52.00   0.50    0.28    --   38.95  32.00 150.00   52
 13  \w     86.00 111.00   0.50    0.28    --   38.95  21.00 -30.00   50
 14  \w    -22.00  51.00   0.50    0.28    --   38.95 -32.00 120.00  146
 15  \w     70.00  96.00   0.50    0.28    --   38.95  65.00   0.00   52
 16  \w     22.00  48.00   0.50    0.28    --   38.95-138.00 -60.00   52
 17  \w     16.00  66.00   0.50    0.28    --   38.95  65.00   0.00  100
 18  \w     79.00 106.00   0.50    0.28    --   38.95  32.00 -60.00   54
 19  \w     76.00 101.00   0.50    0.28    --   38.95  65.00 -30.00   50
 20  \w     26.00  63.00   0.50    0.28    --   38.95  65.00 -30.00   74
 21  \w     37.00  87.00   0.50    0.28    --   38.95  43.00  90.00  100
 22  \w     69.00  94.00   0.50    0.28    --   38.95  32.00 150.00   50
 23  \w     40.00  82.00   0.50    1.11    --  104.92 -61.00 -30.00   84
 24  \w     91.00 157.00   0.50    1.11    --  104.92  22.00 120.00  132
 25  \w     40.00 119.00   0.50    1.11    --  104.92 -45.00  60.00  158
 26  \w     54.00  94.00   0.50    1.11    --  104.92 -61.00 -90.00   80
 27  \w     82.00 114.00   0.50    1.11    --  104.92-111.00 -90.00   64
 28  \w     41.00 109.00   0.50    1.11    --  104.92 -45.00-180.00  136
 29  \w     86.00 157.00   0.50    1.11    --  104.92  53.00 -90.00  142
 30  \w     44.00  78.00   0.50    1.11    --  104.92-111.00 -90.00   68
 31  \w    102.00 157.00   0.50    1.11    --  104.92  45.00 150.00  110
 32  \w     99.00 124.00   0.50    1.11    --  104.92  30.00-150.00   50
 33  \w    121.00 155.00   0.50    1.11    --  104.92 111.00  90.00   68
 34  \w    132.00 157.00   0.50    1.11    --  104.92  93.00 -60.00   50
 35  \w     88.00 154.00   0.50    1.11    --  104.92  61.00  30.00  132
 36  \w     91.00 118.00   0.50    1.11    --  104.92  37.00 -30.00   54
 37  \w     97.00 122.00   0.50    1.11    --  104.92  53.00 -60.00   50
 38  \w     88.00 127.00   0.50    1.11    --  104.92 -61.00 -30.00   78
 39  \w     87.00 144.00   0.50    1.11    --  104.92  22.00 -90.00  114
 40  \w     87.00 117.00   0.50    1.11    --  104.92  93.00 -60.00   60
 41  \w     16.00  41.00   0.50    0.28    --   38.95 -83.00-130.00   50
 42  \w    -20.00  16.00   0.50    0.28    --  -38.95 104.00  90.00   72
 43  \w    -37.00 -11.00   0.50    0.28    --  -38.95  32.00 150.00   52
 44  \w    -76.00 -50.00   0.50    0.28    --  -38.95 104.00  90.00   52
 45  \w     32.00  58.00   0.50    0.28    --   38.95  32.00  90.00   52
 46  \w     13.00  39.00   0.50    0.28    --   38.95 -43.00-120.00   52
 47  \w     13.00  39.00   0.50    0.28    --   38.95-138.00 -60.00   52
 48  \w      9.00  48.00   0.50    0.28    --   38.95 -32.00 -90.00   78
 49  \w     79.00 104.00   0.50    0.28    --   38.95  54.00 150.00   50
 50  \w    -24.00   8.00   0.50    0.28    --   38.95 -43.00-120.00   64
 51  \w     83.00 108.00   0.50    0.28    --   38.95  32.00  90.00   50
 52  \w    -28.00  -2.00   0.50    0.28    --   38.95 -32.00 -90.00   52
 53  \w     48.00  74.00   0.50    0.28    --   38.95-138.00 -60.00   52
 54  \w     39.00  64.00   0.50    0.28    --   38.95  54.00 150.00   50
 55  \w     79.00 105.00   0.50    1.11    --  104.92  77.00  90.00   52
 56  \w     93.00 123.00   0.50    1.11    --  104.92 -86.00 -90.00   60
 57  \w     89.00 114.00   0.50    1.11    --  104.92-111.00 -30.00   50
 58  \w     58.00  84.00   0.50    1.11    --  104.92 -86.00 -90.00   52
 59  \w    101.00 127.00   0.50    1.11    --  104.92  69.00-120.00   52
 60  \w     37.00  64.00   0.50    1.11    --  104.92-111.00 -30.00   54
 61  \w    123.00 157.00   0.50    1.11    --  104.92  69.00 120.00   68
 62  \w     83.00 108.00   0.50    1.11    --  104.92  61.00  90.00   50
 63  \w     34.00  81.00   0.50    1.11    --  104.92   0.00-180.00   94
 64  \w     74.00 124.00   0.50    1.11    --  104.92 -22.00  90.00  100
 65  \w    132.00 157.00   0.50    1.11    --  104.92  69.00-120.00   50
 66  \w     54.00 120.00   0.50    1.11    --  104.92-133.00 -90.00  132
 67  \w     35.00  60.00   0.50    1.11    --  104.92 -22.00  90.00   50
 68  \w     89.00 115.00   0.50    1.11    --  104.92  53.00 120.00   52
 69  \w    119.00 157.00   0.50    1.11    --  104.92  15.00   0.00   76
 70  \w     86.00 120.00   0.50    1.11    --  104.92  53.00  60.00   68
 71  \w     38.00 108.00   0.50    1.11    --  104.92 -37.00 -60.00  140
 72  \w     88.00 128.00   0.50    1.11    --  104.92 -77.00-180.00   80
 73  \w     38.00  64.00   0.50    1.11    --  104.92 -77.00-180.00   52
 74  \w     86.00 136.00   0.50    1.11    --  104.92  93.00 -90.00  100
 75  \w    129.00 157.00   0.50    1.11    --  104.92  77.00  90.00   56
 76  \w     96.00 122.00   0.50    1.11    --  104.92  37.00  90.00   52
 77  \w     36.00  90.50   0.50    1.11    --  104.92 -22.00-180.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0363605000
_diffrn_orient_matrix_UB_12      -0.0371417000
_diffrn_orient_matrix_UB_13      -0.0609089000
_diffrn_orient_matrix_UB_21      -0.0576714000
_diffrn_orient_matrix_UB_22      0.1020909000
_diffrn_orient_matrix_UB_23      -0.0301181000
_diffrn_orient_matrix_UB_31      0.1222136000
_diffrn_orient_matrix_UB_32      0.0591965000
_diffrn_orient_matrix_UB_33      0.0138101000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29610
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.872
_diffrn_reflns_theta_min         3.980
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.140
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       prism
_exptl_crystal_F_000             1336
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.914
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0800P)^2^+2.1645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1376
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5577
_reflns_number_total             6112
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj00965e2.cif
_cod_data_source_block           7680-11822_sp-10
_cod_depositor_comments
'Adding full bibliography for 7058322--7058323.cif.'
_cod_database_code               7058322
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'B F4 N4 S2 O4 C28'
_shelx_estimated_absorpt_t_max   0.687
_shelx_estimated_absorpt_t_min   0.489
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N3(H3)
2.b Ternary CH refined with riding coordinates:
 N1(H1)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3A), C23(H23), C8(H8), C2(H2), C24(H24), C16(H16), C20(H20),
 C27(H27), C26(H26), C17(H17), C19(H19)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C28(H28A,H28B,H28C), C14(H14A,H14B,
 H14C), C21(H21A,H21B,H21C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              9350
_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 1.591
_oxdiff_exptl_absorpt_empirical_full_min 0.666