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_7250807
_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 H20 D7 N2, 0.5(B2 F8)'
_chemical_formula_sum            'C18 H20 B D7 F4 N2'
_chemical_formula_weight         365.27
_chemical_name_common
'2-Methoxy-1,8-bis(dimethylamino)naphthalene hydrogen tetrafluoroborate'
_chemical_temperature_decomposition 573.6(5)
_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             2022-03-25
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.19780(10)
_cell_length_b                   11.48030(10)
_cell_length_c                   12.6584(2)
_cell_measurement_reflns_used    5786
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.8430
_cell_measurement_theta_min      5.1710
_cell_volume                     1772.61(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      100.00(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 0.999
_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   -113.00 -13.00   1.00    1.00    --  -41.19 -57.00  90.00  100
  2  \w    -21.00  74.00   1.00    1.00    --   41.19 -77.00 -90.00   95
  3  \w      8.00  42.00   1.00    1.00    --   41.19  80.00 175.40   34
  4  \w     86.00 178.00   1.00    1.12    --  112.00  45.00  90.00   92
  5  \w     36.00 109.00   1.00    1.12    --  112.00-111.00   0.00   73
  6  \w     30.00 106.00   1.00    1.12    --  112.00 -95.00 120.00   76
  7  \w    104.00 178.00   1.00    1.12    --  112.00 111.00 -90.00   74
  8  \w     36.00 109.00   1.00    1.12    --  112.00-111.00 120.00   73
  9  \w     86.00 178.00   1.00    1.12    --  112.00  45.00-180.00   92
 10  \w    104.00 178.00   1.00    1.12    --  112.00 111.00 120.00   74
 11  \w     86.00 174.00   1.00    1.12    --  112.00  45.00-120.00   88
 12  \w     37.00  87.00   1.00    1.12    --  112.00 -77.00 120.00   50
 13  \w    113.00 139.00   1.00    1.12    --  112.00  32.00  55.00   26
 14  \w     59.00  93.00   1.00    1.12    --  112.00 -95.00  30.00   34
;
_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      -0.0471359000
_diffrn_orient_matrix_UB_12      -0.0614644000
_diffrn_orient_matrix_UB_13      0.0980994000
_diffrn_orient_matrix_UB_21      0.0209054000
_diffrn_orient_matrix_UB_22      -0.1192369000
_diffrn_orient_matrix_UB_23      -0.0520951000
_diffrn_orient_matrix_UB_31      0.1153023000
_diffrn_orient_matrix_UB_32      -0.0035171000
_diffrn_orient_matrix_UB_33      0.0497181000
_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  0.0177
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10119
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.200
_diffrn_reflns_theta_min         5.035
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.906
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.465
_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    1.369
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CD3OD'
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.274
_exptl_crystal_size_min          0.251
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0035(4)
_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   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0526P)^2^+0.9447P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1801
_reflns_number_total             1948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00621j2.cif
_cod_data_source_block           Str_11xDBF4
_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 '300-301 deg.C (decomp.)'. The value was changed to '573.6(5)' --
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               7250807
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H20 B D7 F4 N2'
_shelx_estimated_absorpt_t_max   0.804
_shelx_estimated_absorpt_t_min   0.740
_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. Others
 Fixed Sof: F1(0.5) F2(0.5) F4(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
3.b Idealised Me refined as rotating group:
 C7(D7A,D7B,D7C), C10(H10A,H10B,H10C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              69299
_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 1.187
_oxdiff_exptl_absorpt_empirical_full_min 0.848