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_7250811
_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         'C16 H23 N2 S2, B F4'
_chemical_formula_sum            'C16 H23 B F4 N2 S2'
_chemical_formula_weight         394.29
_chemical_melting_point          491.1(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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-24
_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                86.404(2)
_cell_angle_beta                 76.855(2)
_cell_angle_gamma                81.590(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7857(2)
_cell_length_b                   8.4721(2)
_cell_length_c                   14.0062(4)
_cell_measurement_reflns_used    14410
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.8670
_cell_measurement_theta_min      5.2470
_cell_volume                     889.57(4)
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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   -115.00 -16.00   1.00    1.00    --  -40.82 -38.00 -60.00   99
  2  \w    -65.00  33.00   1.00    1.00    --  -40.82  38.00 120.00   98
  3  \w   -113.00 -13.00   1.00    1.00    --  -40.82 -57.00-150.00  100
  4  \w     27.00  97.00   1.00    1.00    --   40.82-125.00 -60.00   70
  5  \w      6.00  82.00   1.00    1.00    --   40.82 -99.00 150.00   76
  6  \w      5.00  31.00   1.00    1.00    --   40.82  86.00   4.18   26
  7  \w     40.00 141.00   1.00    1.00    --  112.00 -61.00 -90.00  101
  8  \w     61.00 146.00   1.00    1.00    --  112.00 178.00 120.00   85
  9  \w     59.00 178.00   1.00    1.00    --  112.00  15.00   0.00  119
 10  \w     36.00 109.00   1.00    1.00    --  112.00-111.00   0.00   73
 11  \w     36.00 109.00   1.00    1.00    --  112.00-111.00 -90.00   73
 12  \w     84.00 178.00   1.00    1.00    --  112.00  30.00  30.00   94
 13  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00-180.00   76
 14  \w     84.00 178.00   1.00    1.00    --  112.00  30.00 -90.00   94
 15  \w    104.00 178.00   1.00    1.00    --  112.00 111.00  30.00   74
 16  \w     39.00 138.00   1.00    1.00    --  112.00 -45.00 -30.00   99
 17  \w     61.00 146.00   1.00    1.00    --  112.00 178.00 150.00   85
 18  \w     39.00 138.00   1.00    1.00    --  112.00 -45.00 -90.00   99
 19  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00  90.00   76
 20  \w    104.00 178.00   1.00    1.00    --  112.00 111.00-120.00   74
 21  \w     36.00 109.00   1.00    1.00    --  112.00-111.00-120.00   73
 22  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00 150.00   76
 23  \w     40.00 141.00   1.00    1.00    --  112.00 -61.00-120.00  101
 24  \w     39.00 115.00   1.00    1.00    --  112.00-128.00-171.00   76
 25  \w     61.00 146.00   1.00    1.00    --  112.00 178.00  60.00   85
 26  \w     61.00 146.00   1.00    1.00    --  112.00 178.00  90.00   85
 27  \w     39.00 138.00   1.00    1.00    --  112.00 -45.00   0.00   99
 28  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00-150.00   76
 29  \w     36.00 109.00   1.00    1.00    --  112.00-111.00-150.00   73
 30  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00-120.00   76
 31  \w     36.00 109.00   1.00    1.00    --  112.00-111.00  90.00   73
 32  \w     61.00 146.00   1.00    1.00    --  112.00 178.00 -30.00   85
 33  \w     86.00 178.00   1.00    1.00    --  112.00  45.00 -60.00   92
 34  \w     36.00 140.00   1.00    1.00    --  112.00 -30.00  77.70  104
 35  \w     40.00 141.00   1.00    1.00    --  112.00 -61.00-150.00  101
 36  \w     36.00 145.00   1.00    1.00    --  112.00 -77.00 150.00  109
 37  \w   -113.00 -13.00   1.00    1.00    --  -40.82 -57.00  90.00  100
 38  \w   -113.00 -48.00   1.00    1.00    --  -40.82 -57.00  30.00   65
 39  \w    -65.00  33.00   1.00    1.00    --  -40.82  38.00   0.00   98
 40  \w      4.00  30.00   1.00    1.00    --   40.82  89.00-138.83   26
 41  \w      5.00  31.00   1.00    1.00    --   40.82  86.00  66.94   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      -0.0420411000
_diffrn_orient_matrix_UB_12      0.1255195000
_diffrn_orient_matrix_UB_13      -0.0788628000
_diffrn_orient_matrix_UB_21      0.1171714000
_diffrn_orient_matrix_UB_22      -0.1086816000
_diffrn_orient_matrix_UB_23      -0.0806948000
_diffrn_orient_matrix_UB_31      -0.1629954000
_diffrn_orient_matrix_UB_32      -0.0790751000
_diffrn_orient_matrix_UB_33      -0.0062367000
_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  0.0205
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18512
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.178
_diffrn_reflns_theta_min         3.242
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.097
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.457
_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    1.472
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CD3CN/CH2Cl2'
_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.109
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0030(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3713
_refine_ls_number_restraints     205
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0327
_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^)+(0.0136P)^2^+1.0958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0801
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3620
_reflns_number_total             3713
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00621j2.cif
_cod_data_source_block           Str_17xHBF4
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '217-219 deg.C' was changed
to '491.1(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               7250811
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16 H23 B F4 N2 S2'
_shelx_estimated_absorpt_t_max   0.729
_shelx_estimated_absorpt_t_min   0.375
_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. Restrained distances
 F1-B1 \\sim F5-B1
 with sigma of 0.02
 F4-B1 \\sim F6-B1
 with sigma of 0.02
 F3-B1 \\sim F7-B1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F4) = Uanis(F6)
Uanis(F7) = Uanis(F3)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F6)=Sof(F5)=Sof(F7)=1-FVAR(1)
 Sof(F1)=Sof(F3)=Sof(F4)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2), C8(H8), C7(H7)
6.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C12(H12A,H12B,H12C), C11(H11A,H11B,
 H11C), C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              76595
_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 1.293
_oxdiff_exptl_absorpt_empirical_full_min 0.807