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_7250805
_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         '2(Br), C18 H27 N2, H4 N'
_chemical_formula_sum            'C18 H31 Br2 N3'
_chemical_formula_weight         449.28
_chemical_temperature_decomposition 501.1(10)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-22
_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                 107.6710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.84420(10)
_cell_length_b                   8.77120(10)
_cell_length_c                   19.1298(2)
_cell_measurement_reflns_used    12954
_cell_measurement_temperature    100.01(16)
_cell_measurement_theta_max      75.9330
_cell_measurement_theta_min      3.6340
_cell_volume                     2053.46(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      100.01(16)
_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 0.997
_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    -89.00  39.00   1.00    1.00    --  -42.10  17.00 111.00  128
  2  \w   -123.00   4.00   1.00    1.00    --  -42.10 -17.00 -57.00  127
  3  \w     -4.00 123.00   1.00    1.00    --   42.10  17.00 111.00  127
  4  \w     65.00 178.00   1.00    1.21    --  112.00  17.00 111.00  113
  5  \w     31.00 159.00   1.00    1.21    --  112.00 -17.00 -57.00  128
  6  \w      1.00  83.00   1.00    1.00    --   42.10 -99.00-120.00   82
  7  \w      1.00  83.00   1.00    1.00    --   42.10 -99.00 -90.00   82
  8  \w     36.00 113.00   1.00    1.21    --  112.00-111.00  90.00   77
  9  \w     39.00 138.00   1.00    1.21    --  112.00 -45.00  30.00   99
 10  \w     39.00  83.00   1.00    1.21    --  112.00-111.00-120.00   44
 11  \w     85.00 178.00   1.00    1.21    --  112.00  30.00   0.00   93
 12  \w     54.00 110.00   1.00    1.21    --  112.00-111.00   0.00   56
 13  \w     93.00 160.00   1.00    1.21    --  112.00  30.00  60.00   67
 14  \w     41.00 109.00   1.00    1.21    --  112.00 -45.00  90.00   68
 15  \w     85.00 178.00   1.00    1.21    --  112.00  30.00 -90.00   93
 16  \w     37.00  63.00   1.00    1.21    --  112.00-111.00-150.00   26
 17  \w     85.00 111.00   1.00    1.21    --  112.00-111.00-150.00   26
 18  \w     31.00  56.00   1.00    1.21    --  112.00 -95.00  60.00   25
 19  \w     74.00 100.00   1.00    1.21    --  112.00 -95.00  60.00   26
 20  \w    109.00 143.00   1.00    1.21    --  112.00  61.00 -60.00   34
 21  \w     41.00 110.00   1.00    1.21    --  112.00 -95.00 -90.00   69
 22  \w    120.00 176.00   1.00    1.21    --  112.00 111.00 120.00   56
 23  \w     75.00 101.00   1.00    1.21    --  112.00 178.00-120.00   26
 24  \w    124.00 150.00   1.00    1.21    --  112.00 178.00-120.00   26
 25  \w     77.00 111.00   1.00    1.21    --  112.00-111.00  60.00   34
 26  \w    147.00 174.00   1.00    1.21    --  112.00 111.00-120.00   27
 27  \w    101.00 127.00   1.00    1.21    --  112.00 111.00  60.00   26
 28  \w     33.00  87.00   1.00    1.21    --  112.00 -95.00 -60.00   54
;
_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      0.0804130000
_diffrn_orient_matrix_UB_12      0.0346283000
_diffrn_orient_matrix_UB_13      0.0762834000
_diffrn_orient_matrix_UB_21      -0.0966718000
_diffrn_orient_matrix_UB_22      0.0184210000
_diffrn_orient_matrix_UB_23      0.0311648000
_diffrn_orient_matrix_UB_31      0.0058773000
_diffrn_orient_matrix_UB_32      -0.1712521000
_diffrn_orient_matrix_UB_33      0.0187225000
_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  0.0247
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21893
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.269
_diffrn_reflns_theta_min         3.689
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.017
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.745
_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    1.453
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile/chloroform'
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0232
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0297P)^2^+1.0738P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0602
_refine_ls_wR_factor_ref         0.0615
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3974
_reflns_number_total             4288
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00621j2.cif
_cod_data_source_block           Str_7xHBrxNH4Br
_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 '227-229 deg.C (decomp.)'. The value was changed to '501.1(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_original_cell_volume        2053.45(4)
_cod_database_code               7250805
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C18 H27 Br N2'
_shelx_estimated_absorpt_t_max   0.672
_shelx_estimated_absorpt_t_min   0.254
_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), C7(H7)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C14(H14A,H14B,
 H14C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C18(H18A,
 H18B,H18C)
;
_shelx_res_checksum              23657
_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 2.032
_oxdiff_exptl_absorpt_empirical_full_min 0.621