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_7250812
_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         'C18 H27 N2 S2, B F4'
_chemical_formula_sum            'C18 H27 B F4 N2 S2'
_chemical_formula_weight         422.34
_chemical_temperature_decomposition 551.6(15)
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-04
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2025-06-13 deposited with the CCDC.	2025-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                106.729(2)
_cell_angle_beta                 108.330(2)
_cell_angle_gamma                104.687(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0876(2)
_cell_length_b                   10.7862(2)
_cell_length_c                   11.0225(3)
_cell_measurement_reflns_used    15070
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.8780
_cell_measurement_theta_min      4.5860
_cell_volume                     1009.18(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_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    -69.00  32.00   1.00    1.00    --  -40.82  57.00  60.00  101
  2  \w    -65.00  33.00   1.00    1.00    --  -40.82  38.00-150.00   98
  3  \w    -69.00  32.00   1.00    1.00    --  -40.82  57.00 -60.00  101
  4  \w      7.00  34.00   1.00    1.00    --   40.82  83.00-176.91   27
  5  \w      8.00  42.00   1.00    1.00    --   40.82  80.00  64.51   34
  6  \w     16.00 115.00   1.00    1.00    --   40.82  38.00 150.00   99
  7  \w      6.00  32.00   1.00    1.00    --   40.82  85.00 -54.39   26
  8  \w      5.00  31.00   1.00    1.00    --   40.82  87.00 145.98   26
  9  \w     36.00 109.00   1.00    1.00    --  112.00-111.00  60.00   73
 10  \w     36.00 109.00   1.00    1.00    --  112.00-111.00-180.00   73
 11  \w     39.00 138.00   1.00    1.00    --  112.00 -45.00 -30.00   99
 12  \w     36.00 145.00   1.00    1.00    --  112.00 -77.00-150.00  109
 13  \w     84.00 178.00   1.00    1.00    --  112.00  30.00 -30.00   94
 14  \w     84.00 178.00   1.00    1.00    --  112.00  30.00 150.00   94
 15  \w     38.00 143.00   1.00    1.00    --  112.00 -71.00  60.03  105
 16  \w     86.00 178.00   1.00    1.00    --  112.00  45.00  90.00   92
 17  \w     36.00 109.00   1.00    1.00    --  112.00-111.00 -60.00   73
 18  \w     36.00 109.00   1.00    1.00    --  112.00-111.00   0.00   73
 19  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00 -90.00   76
 20  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00-180.00   76
 21  \w     36.00 145.00   1.00    1.00    --  112.00 -77.00  30.00  109
 22  \w     36.00 145.00   1.00    1.00    --  112.00 -77.00-180.00  109
 23  \w    103.00 178.00   1.00    1.00    --  112.00  77.00-150.00   75
 24  \w     61.00 146.00   1.00    1.00    --  112.00 178.00  30.00   85
 25  \w     36.00 109.00   1.00    1.00    --  112.00-111.00 150.00   73
 26  \w    104.00 178.00   1.00    1.00    --  112.00 111.00-180.00   74
 27  \w     36.00 145.00   1.00    1.00    --  112.00 -77.00 -30.00  109
 28  \w     86.00 178.00   1.00    1.00    --  112.00  45.00   0.00   92
 29  \w    103.00 178.00   1.00    1.00    --  112.00  77.00 -60.00   75
 30  \w     61.00 146.00   1.00    1.00    --  112.00 178.00 120.00   85
 31  \w     36.00 109.00   1.00    1.00    --  112.00-111.00 -90.00   73
 32  \w     40.00 141.00   1.00    1.00    --  112.00 -61.00 -30.00  101
 33  \w     30.00 165.00   1.00    1.00    --  112.00 -15.00 120.00  135
 34  \w     36.00 109.00   1.00    1.00    --  112.00-111.00 120.00   73
 35  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00  30.00   76
 36  \w     61.00 146.00   1.00    1.00    --  112.00 178.00  60.00   85
 37  \w     61.00 146.00   1.00    1.00    --  112.00 178.00 150.00   85
 38  \w     86.00 178.00   1.00    1.00    --  112.00  45.00-120.00   92
 39  \w     83.00 178.00   1.00    1.00    --  112.00  61.00 150.00   95
 40  \w     80.00 106.00   1.00    1.00    --  112.00 -82.00 -10.05   26
 41  \w     53.00  79.00   1.00    1.00    --  112.00 -82.00 -10.05   26
;
_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      -0.0227062000
_diffrn_orient_matrix_UB_12      0.0378455000
_diffrn_orient_matrix_UB_13      0.1358734000
_diffrn_orient_matrix_UB_21      0.1579592000
_diffrn_orient_matrix_UB_22      0.1176290000
_diffrn_orient_matrix_UB_23      0.0772024000
_diffrn_orient_matrix_UB_31      -0.0688728000
_diffrn_orient_matrix_UB_32      0.1034048000
_diffrn_orient_matrix_UB_33      -0.0373290000
_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  0.0389
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20852
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.145
_diffrn_reflns_theta_min         4.612
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.766
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.394
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone'
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.212
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0305
_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^)+(0.0449P)^2^+0.3857P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0823
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4089
_reflns_number_total             4205
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00621j2.cif
_cod_data_source_block           Str_8xHBF4
_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 '277-280 deg.C (decomp.)'. The value was changed to '551.6(15)' --
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_original_cell_volume        1009.18(4)
_cod_database_code               7250812
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H27 B F4 N2 S2'
_shelx_estimated_absorpt_t_max   0.592
_shelx_estimated_absorpt_t_min   0.385
_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:
 C7(H7), C3(H3)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C11(H11A,H11B,H11C), C17(H17A,H17B,
 H17C), C15(H15A,H15B,H15C), C13(H13A,H13B,H13C), C18(H18A,H18B,H18C), C14(H14A,
 H14B,H14C)
;
_shelx_res_checksum              80994
_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 1.435
_oxdiff_exptl_absorpt_empirical_full_min 0.701