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_7250804
_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 H15 Br4 N2, B F4'
_chemical_formula_sum            'C14 H15 B Br4 F4 N2'
_chemical_formula_weight         617.73
_chemical_temperature_decomposition 486.6(15)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-06-13 deposited with the CCDC.	2025-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.6600(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.75460(10)
_cell_length_b                   9.55370(10)
_cell_length_c                   14.49040(10)
_cell_measurement_reflns_used    9730
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.6690
_cell_measurement_theta_min      3.2160
_cell_volume                     1904.02(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_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     92.00 175.00   0.50    0.15    --  113.25  77.00   0.00  166
  2  \w    148.00 174.00   0.50    0.15    --  113.25  61.00 -30.00   52
  3  \w    107.00 136.00   0.50    0.15    --  113.25  61.00 -30.00   58
  4  \w    140.00 167.00   0.50    0.15    --  113.25  45.00  30.00   54
  5  \w    106.00 178.00   0.50    0.15    --  113.25  30.00  60.00  144
  6  \w    109.00 154.00   0.50    0.15    --  113.25  30.00 150.00   90
  7  \w    -94.00 -37.00   0.50    0.15    -- -106.00  77.00  60.00  114
  8  \w    -66.00 -33.00   0.50    0.15    -- -106.00  61.00  90.00   66
  9  \w    -70.00 -34.00   0.50    0.15    -- -106.00  61.00  60.00   72
 10  \w    -84.00 -33.00   0.50    0.15    -- -106.00  77.00 -90.00  102
 11  \w    -60.00 -33.00   0.50    0.15    -- -106.00  61.00-150.00   54
 12  \w     74.00 103.00   0.50    0.05    --   47.44 125.00  30.00   58
 13  \w     74.00  99.00   0.50    0.05    --   47.44 125.00   0.00   50
 14  \w    143.00 169.00   0.50    0.15    --  113.25  87.00  79.00   52
 15  \w    -26.00  38.00   0.50    0.05    --   47.44 -37.00-150.00  128
 16  \w     44.00  70.00   0.50    0.15    --  113.25 -61.00-150.00   52
 17  \w     46.00  71.00   0.50    0.15    --  113.25 -61.00 -30.00   50
 18  \w     43.00  69.00   0.50    0.15    --  113.25 -61.00 120.00   52
 19  \w    108.00 139.00   0.50    0.15    --  113.25 -87.00 -38.00   62
 20  \w     43.00 102.00   0.50    0.15    --  113.25 -87.00 -38.00  118
 21  \w     61.00  99.00   0.50    0.15    --  113.25 -94.00-150.00   76
 22  \w    -21.00  57.00   0.50    0.05    --   47.44 -87.00 -38.00  156
 23  \w    -62.00 -36.00   0.50    0.15    -- -106.00  87.00  79.00   52
 24  \w    -74.00  22.00   0.50    0.05    --  -47.44  87.00  79.00  192
 25  \w    -78.00 -38.00   0.50    0.15    -- -106.00 125.00-120.00   80
 26  \w   -110.00 -82.00   0.50    0.15    -- -106.00 125.00-120.00   56
 27  \w   -176.00 -80.00   0.50    0.15    -- -106.00 -87.00 -38.00  192
 28  \w   -109.00 -74.00   0.50    0.05    --  -47.44-125.00  30.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0461856000
_diffrn_orient_matrix_UB_12      -0.1356480000
_diffrn_orient_matrix_UB_13      0.0367046000
_diffrn_orient_matrix_UB_21      0.1007628000
_diffrn_orient_matrix_UB_22      -0.0505780000
_diffrn_orient_matrix_UB_23      0.0335916000
_diffrn_orient_matrix_UB_31      -0.0164726000
_diffrn_orient_matrix_UB_32      0.0709849000
_diffrn_orient_matrix_UB_33      0.0939220000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14556
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.995
_diffrn_reflns_theta_min         3.213
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.155
_exptl_crystal_description       plate
_exptl_crystal_F_000             1176
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.045
_refine_diff_density_min         -0.861
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3612
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0275
_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^)+(0.0419P)^2^+1.4385P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0724
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3400
_reflns_number_total             3612
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00621j2.cif
_cod_data_source_block           Str_4xHBF4
_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 '212-215 deg.C (decomp.)'. The value was changed to '486.6(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               7250804
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C14 H15 Br4 N2 B F4'
_shelx_estimated_absorpt_t_max   0.815
_shelx_estimated_absorpt_t_min   0.280
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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
 N1-H1
 1 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_shelx_res_checksum              63578
_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 2.351
_oxdiff_exptl_absorpt_empirical_full_min 0.616