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_7250808
_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         'C14 H17 N2 S2, C H2 Cl2, B F4'
_chemical_formula_sum            'C15 H19 B Cl2 F4 N2 S2'
_chemical_formula_weight         449.15
_chemical_temperature_decomposition 519.6(15)
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-11
_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                90
_cell_angle_beta                 97.067(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3768(2)
_cell_length_b                   12.6149(3)
_cell_length_c                   13.7199(2)
_cell_measurement_reflns_used    7114
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.0810
_cell_measurement_theta_min      5.1990
_cell_volume                     1954.08(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (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 0.999
_diffrn_measured_fraction_theta_max 0.998
_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 -10.00   1.00    1.00    --  -42.10 -77.00 159.00  108
  2  \w     36.00 145.00   1.00    1.32    --  112.00 -77.00 159.00  109
  3  \w     79.00 178.00   1.00    1.32    --  112.00  77.00 -74.00   99
  4  \w    -75.00  34.00   1.00    1.00    --  -42.10  77.00 -74.00  109
  5  \w     23.00  98.00   1.00    1.00    --   42.10-125.00-180.00   75
  6  \w      1.00  83.00   1.00    1.00    --   42.10 -99.00  30.00   82
  7  \w     83.00 178.00   1.00    1.32    --  112.00  61.00-180.00   95
  8  \w     79.00 178.00   1.00    1.32    --  112.00  77.00-120.00   99
  9  \w     83.00 178.00   1.00    1.32    --  112.00  61.00-150.00   95
 10  \w     30.00 110.00   1.00    1.32    --  112.00 -95.00 150.00   80
 11  \w     40.00 141.00   1.00    1.32    --  112.00 -61.00  60.00  101
 12  \w     39.00 138.00   1.00    1.32    --  112.00 -45.00-180.00   99
 13  \w     83.00 178.00   1.00    1.32    --  112.00  61.00 120.00   95
 14  \w     36.00 113.00   1.00    1.32    --  112.00-111.00  60.00   77
 15  \w     38.00 137.00   1.00    1.32    --  112.00 -40.00  52.64   99
 16  \w     39.00 138.00   1.00    1.32    --  112.00 -45.00-150.00   99
 17  \w     30.00 110.00   1.00    1.32    --  112.00 -95.00-150.00   80
 18  \w     38.00 107.00   1.00    1.32    --  112.00 -72.00 165.85   69
 19  \w     37.00 113.00   1.00    1.32    --  112.00-111.00   0.00   76
;
_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      -0.0336531000
_diffrn_orient_matrix_UB_12      0.0759205000
_diffrn_orient_matrix_UB_13      0.0799994000
_diffrn_orient_matrix_UB_21      0.1090646000
_diffrn_orient_matrix_UB_22      0.0688235000
_diffrn_orient_matrix_UB_23      -0.0121258000
_diffrn_orient_matrix_UB_31      -0.0747052000
_diffrn_orient_matrix_UB_32      0.0664331000
_diffrn_orient_matrix_UB_33      -0.0791275000
_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  0.0300
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10653
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.415
_diffrn_reflns_theta_min         5.258
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.355
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.449
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.863
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2144
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0727P)^2^+4.2499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2038
_reflns_number_total             2144
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00621j2.cif
_cod_data_source_block           Str_15xHBF4
_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 '245-248 deg.C (decomp.)'. The value was changed to '519.6(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_database_code               7250808
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C14 H18 N2 S2, B F4'
_shelx_estimated_absorpt_t_max   0.559
_shelx_estimated_absorpt_t_min   0.229
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 F1, F3, F2, B1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F3, B1, F1, F2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: H1(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
4.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              45383
_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 1.495
_oxdiff_exptl_absorpt_empirical_full_min 0.718