Intramolecular hydrogen bonding in 1,8-bis(dimethylamino)naphthalenes containing two to four heteroatomic functions in the ortho- and peri-positions: from CD3 to sulfur and selenium
Ozeryanskii, Valery A.; Demidov, Oleg P.; Marchenko, Andrey V.; CrystEngComm 27 (2025) 6163–6173; doi:10.1039/D5CE00621J

data_7250806
_publ_section_title
;
 Intramolecular hydrogen bonding in 1,8-bis(dimethylamino)naphthalenes
 containing two to four heteroatomic functions in the ortho- and
 peri-positions: from CD3 to sulfur and selenium
;
_journal_issue                   37
_journal_name_full               CrystEngComm
_journal_page_first              6163
_journal_page_last               6173
_journal_paper_doi               10.1039/D5CE00621J
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         '2(C18 H27 N2 S4), 2(B F4), C7 H8'
_chemical_formula_sum            'C43 H62 B2 F8 N4 S8'
_chemical_formula_weight         1065.06
_chemical_temperature_decomposition 498.1(10)
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-06-07
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-06-13 deposited with the CCDC.	2025-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                71.122(2)
_cell_angle_beta                 78.938(2)
_cell_angle_gamma                80.513(2)
_cell_formula_units_Z            2
_cell_length_a                   12.0536(2)
_cell_length_b                   14.2355(4)
_cell_length_c                   15.5369(3)
_cell_measurement_reflns_used    19725
_cell_measurement_temperature    100.2(9)
_cell_measurement_theta_max      79.2660
_cell_measurement_theta_min      3.0430
_cell_volume                     2460.49(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.2(9)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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   -118.00 -39.00   0.50    0.25    --  -47.35 -42.00-106.00  158
  2  \w    -16.00  11.00   0.50    0.25    --  -47.35  42.00  45.00   54
  3  \w     58.00 113.00   0.50    0.25    --   47.35  42.00  45.00  110
  4  \w    -20.00  46.00   0.50    0.25    --   47.35 -42.00-106.00  132
  5  \w   -164.00-116.00   0.50    0.90    -- -106.00 -42.00-106.00   96
  6  \w    102.00 178.00   0.50    0.90    --  113.25  42.00  45.00  152
  7  \w   -119.00 -93.00   0.50    0.25    --  -47.35-125.00-150.00   52
  8  \w     -5.00  41.00   0.50    0.25    --   47.35 -37.00 -30.00   92
  9  \w     30.00  69.00   0.50    0.25    --   47.35 -77.00  60.00   78
 10  \w    -25.00  26.00   0.50    0.25    --   47.35 -19.00 120.00  102
 11  \w     34.00  85.00   0.50    0.25    --   47.35-125.00-150.00  102
 12  \w     76.00 102.00   0.50    0.25    --   47.35 125.00 -90.00   52
 13  \w    -11.00  14.00   0.50    0.25    --   47.35 -77.00  60.00   50
 14  \w   -112.00 -87.00   0.50    0.90    -- -106.00 125.00  90.00   50
 15  \w   -154.00 -94.00   0.50    0.90    -- -106.00 -15.00 -30.00  120
 16  \w    -81.00 -52.00   0.50    0.90    -- -106.00 135.00  85.81   58
 17  \w   -108.00 -82.00   0.50    0.90    -- -106.00 112.00 152.26   52
 18  \w   -102.00 -36.00   0.50    0.90    -- -106.00 125.00   0.00  132
 19  \w    -71.00 -43.00   0.50    0.90    -- -106.00  61.00-150.00   56
 20  \w    -79.00 -42.00   0.50    0.90    -- -106.00 125.00  90.00   74
 21  \w    -66.00 -40.00   0.50    0.90    -- -106.00  61.00 -60.00   52
 22  \w   -107.00 -81.00   0.50    0.90    -- -106.00 108.00  80.97   52
 23  \w    -82.00 -56.00   0.50    0.90    -- -106.00 143.00 -40.87   52
 24  \w    -81.00 -33.00   0.50    0.90    -- -106.00 137.00 -92.40   96
 25  \w   -125.00 -99.00   0.50    0.90    -- -106.00 143.00 -40.87   52
 26  \w   -141.00-106.00   0.50    0.90    -- -106.00 -30.00-150.00   70
 27  \w   -119.00 -85.00   0.50    0.90    -- -106.00 135.00  85.81   68
 28  \w    -60.00 -35.00   0.50    0.90    -- -106.00  61.00 -90.00   50
 29  \w    -69.00 -44.00   0.50    0.90    -- -106.00  61.00 -30.00   50
 30  \w   -120.00 -90.00   0.50    0.90    -- -106.00 137.00 -92.40   60
 31  \w     44.00  70.00   0.50    0.90    --  113.25 -77.00-150.00   52
 32  \w     64.00  91.00   0.50    0.90    --  113.25 -94.00 -30.00   54
 33  \w     93.00 129.00   0.50    0.90    --  113.25-149.00 -10.74   72
 34  \w     49.00  76.00   0.50    0.90    --  113.25-149.00 -10.74   54
 35  \w     98.00 173.00   0.50    0.90    --  113.25  61.00  60.00  150
 36  \w     72.00  98.00   0.50    0.90    --  113.25 -77.00-150.00   52
 37  \w    102.00 169.00   0.50    0.90    --  113.25  45.00   0.00  134
 38  \w    102.00 161.00   0.50    0.90    --  113.25  30.00-180.00  118
 39  \w     46.00  71.00   0.50    0.90    --  113.25 -61.00  60.00   50
 40  \w     51.00 105.00   0.50    0.90    --  113.25 -77.00  30.00  108
 41  \w    104.00 177.00   0.50    0.90    --  113.25  15.00 150.00  146
 42  \w     42.00  79.00   0.50    0.90    --  113.25 -94.00-180.00   74
 43  \w     43.00 110.00   0.50    0.90    --  113.25-125.00 -90.00  134
 44  \w    104.00 177.00   0.50    0.90    --  113.25  45.00  90.00  146
 45  \w     70.00 105.00   0.50    0.90    --  113.25 -94.00 150.00   70
 46  \w     56.00 107.00   0.50    0.90    --  113.25-125.00 150.00  102
 47  \w     46.00 109.00   0.50    0.90    --  113.25-125.00   0.00  126
 48  \w     42.00 104.50   0.50    0.90    --  113.25-125.00-120.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1057428000
_diffrn_orient_matrix_UB_12      0.0233516000
_diffrn_orient_matrix_UB_13      -0.0486320000
_diffrn_orient_matrix_UB_21      -0.0120864000
_diffrn_orient_matrix_UB_22      -0.1124476000
_diffrn_orient_matrix_UB_23      0.0284345000
_diffrn_orient_matrix_UB_31      -0.0764346000
_diffrn_orient_matrix_UB_32      0.0073029000
_diffrn_orient_matrix_UB_33      0.0897505000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28891
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.498
_diffrn_reflns_theta_max         67.498
_diffrn_reflns_theta_min         3.040
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.936
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       prism
_exptl_crystal_F_000             1116
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile/ethanol/toluene'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     611
_refine_ls_number_reflns         8824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0642P)^2^+0.9541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1116
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7861
_reflns_number_total             8824
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00621j2.cif
_cod_data_source_block           Str_12xHBF4
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_chemical_melting_point' was changed to
'_chemical_temperature_decomposition' since the value had been given
as '224-226 deg.C (decomp.)'. The value was changed to '498.1(10)' --
it was converted from degrees Celsius (C) to kelvins (K), the average
value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7250802--7250812.cif.
;
_cod_database_code               7250806
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C43 H62 S8 B2 F8 N4'
_shelx_estimated_absorpt_t_max   0.798
_shelx_estimated_absorpt_t_min   0.572
_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:
 C3A(H3A), C6A(H6A), C6(H6), C3(H3), C6S(H6S), C5S(H5S), C2S(H2S), C3S(H3S),
 C4S(H4S)
2.b Idealised Me refined as rotating group:
 C14A(H14D,H14E,H14F), C11A(H11D,H11E,H11F), C12(H12A,H12B,H12C), C17A(H17D,
 H17E,H17F), C17(H17A,H17B,H17C), C13A(H13D,H13E,H13F), C16(H16A,H16B,H16C),
 C12A(H12D,H12E,H12F), C15A(H15D,H15E,H15F), C13(H13A,H13B,H13C), C11(H11A,H11B,
 H11C), C18(H18A,H18B,H18C), C14(H14A,H14B,H14C), C16A(H16D,H16E,H16F),
 C15(H15A,H15B,H15C), C18A(H18D,H18E,H18F), C7S(H7SA,H7SB,H7SC)
;
_shelx_res_checksum              44304
_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 1.465
_oxdiff_exptl_absorpt_empirical_full_min 0.679