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_7250802
_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         'B F4, C16 H22 D N2'
_chemical_formula_sum            'C16 H22 B D F4 N2'
_chemical_formula_weight         331.18
_chemical_name_common
'2-Methoxy-1,8-bis(dimethylamino)naphthalene hydrogen tetrafluoroborate'
_chemical_temperature_decomposition 501.6(5)
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-17
_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                   7.15330(10)
_cell_length_b                   13.3033(2)
_cell_length_c                   17.4216(2)
_cell_measurement_reflns_used    6632
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.1240
_cell_measurement_theta_min      4.1460
_cell_volume                     1657.88(4)
_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      99.99(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   -115.00 -64.00   1.00    1.00    --  -42.10-139.00 -55.00   51
  2  \w     33.00 150.00   1.00    3.19    --  112.00 -21.00 168.00  117
  3  \w     39.00 121.00   1.00    3.19    --  112.00-130.00 118.00   82
  4  \w    101.00 178.00   1.00    3.19    --  112.00 104.00 114.00   77
  5  \w   -121.00  -5.00   1.00    1.00    --  -42.10 -21.00 168.00  116
  6  \w   -116.00 -18.00   1.00    1.00    --  -42.10 -38.00  90.00   98
  7  \w     23.00  98.00   1.00    1.00    --   42.10-125.00   0.00   75
  8  \w     36.00 113.00   1.00    3.19    --  112.00-111.00   0.00   77
  9  \w     86.00 171.00   1.00    3.19    --  112.00  45.00  30.00   85
 10  \w    139.00 165.00   1.00    3.19    --  112.00 111.00-120.00   26
 11  \w     81.00 122.00   1.00    3.19    --  112.00 -30.00-150.00   41
 12  \w     40.00  89.00   1.00    3.19    --  112.00-111.00 -60.00   49
 13  \w     36.00 113.00   1.00    3.19    --  112.00-111.00-150.00   77
 14  \w    115.00 142.00   1.00    3.19    --  112.00 111.00-150.00   27
 15  \w     88.00 113.00   1.00    3.19    --  112.00-111.00 -30.00   25
;
_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      0.0191774000
_diffrn_orient_matrix_UB_12      -0.1045532000
_diffrn_orient_matrix_UB_13      -0.0371890000
_diffrn_orient_matrix_UB_21      0.0554446000
_diffrn_orient_matrix_UB_22      0.0496456000
_diffrn_orient_matrix_UB_23      -0.0765642000
_diffrn_orient_matrix_UB_31      0.2072105000
_diffrn_orient_matrix_UB_32      -0.0036074000
_diffrn_orient_matrix_UB_33      0.0239952000
_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  0.0249
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10264
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.234
_diffrn_reflns_theta_min         4.181
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.925
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.522
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CD3OD'
_exptl_crystal_size_max          0.458
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1280 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3369
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0487P)^2^+0.2025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                3226
_reflns_number_total             3369
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00621j2.cif
_cod_data_source_block           Str_21xDBF4
_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 '228-229 deg.C (decomp.)'. The value was changed to '501.6(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               7250802
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C16 H22 B D F4 N2'
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.677
_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
 F2-B1 \\sim F2A-B1
 with sigma of 0.02
 F1-B1 \\sim F1A-B1
 with sigma of 0.02
 F4-B1 \\sim F4A-B1
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F3, F2, F1, F4, B1, F2A, F1A, F4A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F2A)=Sof(F1A)=Sof(F4A)=1-FVAR(1)
 Sof(F2)=Sof(F1)=Sof(F4)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C3(H3), C7(H7)
5.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C14(H14A,H14B,H14C), C11(H11A,H11B,H11C), C15(H15A,H15B,
 H15C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              286
_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 1.263
_oxdiff_exptl_absorpt_empirical_full_min 0.762