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_7250809
_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         'C N S, C18 H27 N2'
_chemical_formula_sum            'C19 H27 N3 S'
_chemical_formula_weight         329.49
_chemical_melting_point          525.1(10)
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-13
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-06-13 deposited with the CCDC.	2025-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.02790(10)
_cell_length_b                   11.51430(10)
_cell_length_c                   12.81780(10)
_cell_measurement_reflns_used    6838
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.1750
_cell_measurement_theta_min      5.0120
_cell_volume                     1775.17(3)
_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 1.000
_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    -77.00  36.00   1.00    1.00    --  -42.10  85.00 -51.00  113
  2  \w     85.00 178.00   1.00    1.00    --  112.00  50.00-169.00   93
  3  \w    101.00 178.00   1.00    1.00    --  112.00  91.00  49.00   77
  4  \w     30.00 147.00   1.00    1.00    --  112.00 -85.00-169.00  117
  5  \w    -68.00  29.00   1.00    1.00    --  -42.10  50.00-169.00   97
  6  \w      3.00  54.00   1.00    1.00    --   42.10 -99.00  60.00   51
  7  \w     30.00  90.00   1.00    1.00    --  112.00 -95.00  90.00   60
  8  \w    112.00 175.00   1.00    1.00    --  112.00  45.00 -60.00   63
  9  \w     31.00 104.00   1.00    1.00    --  112.00 -95.00-120.00   73
 10  \w     88.00 139.00   1.00    1.00    --  112.00  30.00  60.00   51
 11  \w     84.00 155.00   1.00    1.00    --  112.00  61.00-120.00   71
 12  \w     96.00 144.00   1.00    1.00    --  112.00 178.00 -60.00   48
 13  \w     69.00 112.00   1.00    1.00    --  112.00 -61.00-150.00   43
 14  \w    130.00 156.00   1.00    1.00    --  112.00  36.00 104.57   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      0.0396106000
_diffrn_orient_matrix_UB_12      0.1213916000
_diffrn_orient_matrix_UB_13      -0.0341769000
_diffrn_orient_matrix_UB_21      0.1065366000
_diffrn_orient_matrix_UB_22      -0.0151011000
_diffrn_orient_matrix_UB_23      0.0653728000
_diffrn_orient_matrix_UB_31      0.0590814000
_diffrn_orient_matrix_UB_32      -0.0541761000
_diffrn_orient_matrix_UB_33      -0.0948765000
_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  0.0208
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10355
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.355
_diffrn_reflns_theta_min         5.042
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.626
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.232
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Toluene'
_exptl_crystal_size_max          0.479
_exptl_crystal_size_mid          0.351
_exptl_crystal_size_min          0.205
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0628P)^2^+0.9929P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1883
_reflns_number_total             1958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00621j2.cif
_cod_data_source_block           Str_7xHSCN
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '251-253 deg.C' was changed
to '525.1(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               7250809
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C19 H27 N3 S'
_shelx_estimated_absorpt_t_max   0.732
_shelx_estimated_absorpt_t_min   0.510
_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:
 C3(H3)
2.b Idealised Me refined as rotating group:
 C00A(H00A,H00B,H00C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              71762
_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 1.450
_oxdiff_exptl_absorpt_empirical_full_min 0.767