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_7250803
_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 H19 N2, Cl O4'
_chemical_formula_sum            'C14 H19 Cl N2 O4'
_chemical_formula_weight         314.76
_chemical_temperature_decomposition 570.1(10)
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-12-02
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-06-13 deposited with the CCDC.	2025-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                84.836(4)
_cell_angle_beta                 73.423(5)
_cell_angle_gamma                78.518(5)
_cell_formula_units_Z            2
_cell_length_a                   8.1255(5)
_cell_length_b                   8.1953(4)
_cell_length_c                   12.3764(6)
_cell_measurement_reflns_used    10417
_cell_measurement_temperature    296.17(16)
_cell_measurement_theta_max      75.7990
_cell_measurement_theta_min      3.6800
_cell_volume                     773.61(8)
_computing_cell_refinement       'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.90 64-bit (release 15-09-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_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      air
_diffrn_ambient_temperature      296.17(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 0.989
_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    -75.00  37.00   1.00    6.15    --  -41.19  81.00 -26.00  112
  2  \w    -21.00  75.00   1.00    6.15    --   41.19 -81.00-149.00   96
  3  \w     34.00 146.00   1.00   24.58    --  112.00 -81.00-149.00  112
  4  \w    103.00 178.00   1.00   24.58    --  112.00  81.00 -26.00   75
  5  \w    -87.00  -6.00   1.00    6.15    --  -41.19 125.00  90.00   81
  6  \w   -113.00 -13.00   1.00    6.15    --  -41.19 -57.00-150.00  100
  7  \w      6.00  32.00   1.00    6.15    --   41.19  85.00  62.81   26
  8  \w     17.00 115.00   1.00    6.15    --   41.19  38.00 120.00   98
  9  \w      7.00  34.00   1.00    6.15    --   41.19  83.00  88.39   27
 10  \w     39.00 138.00   1.00   24.58    --  112.00 -45.00  60.00   99
 11  \w    103.00 178.00   1.00   24.58    --  112.00  77.00 120.00   75
 12  \w     86.00 178.00   1.00   24.58    --  112.00  45.00  60.00   92
 13  \w     59.00 178.00   1.00   24.58    --  112.00  15.00-180.00  119
 14  \w     39.00 109.00   1.00   24.58    --  112.00-111.00 -60.00   70
 15  \w     59.00 178.00   1.00   24.58    --  112.00  15.00-180.00  119
 16  \w     39.00 109.00   1.00   24.58    --  112.00-111.00-150.00   70
 17  \w     39.00 109.00   1.00   24.58    --  112.00-111.00 -30.00   70
 18  \w     84.00 178.00   1.00   24.58    --  112.00  30.00-120.00   94
 19  \w    103.00 178.00   1.00   24.58    --  112.00  77.00 120.00   75
 20  \w     39.00 109.00   1.00   24.58    --  112.00-111.00 -60.00   70
 21  \w     39.00 109.00   1.00   24.58    --  112.00-111.00 120.00   70
 22  \w     30.00 106.00   1.00   24.58    --  112.00 -95.00  30.00   76
 23  \w     39.00 109.00   1.00   24.58    --  112.00-111.00   0.00   70
 24  \w    103.00 178.00   1.00   24.58    --  112.00  77.00-180.00   75
 25  \w     39.00 109.00   1.00   24.58    --  112.00-111.00 -90.00   70
 26  \w     84.00 178.00   1.00   24.58    --  112.00  30.00-120.00   94
 27  \w     39.00 109.00   1.00   24.58    --  112.00-111.00 150.00   70
 28  \w     40.00 141.00   1.00   24.58    --  112.00 -61.00 -90.00  101
 29  \w    103.00 178.00   1.00   24.58    --  112.00  77.00 -60.00   75
 30  \w     30.00 106.00   1.00   24.58    --  112.00 -95.00-150.00   76
 31  \w     36.00 140.00   1.00   24.58    --  112.00 -30.00-180.00  104
 32  \w     86.00 178.00   1.00   24.58    --  112.00  45.00  60.00   92
 33  \w     39.00 109.00   1.00   24.58    --  112.00-111.00  30.00   70
 34  \w     40.00 141.00   1.00   24.58    --  112.00 -61.00   0.00  101
 35  \w     36.00 140.00   1.00   24.58    --  112.00 -30.00 120.00  104
 36  \w     39.00 109.00   1.00   24.58    --  112.00-111.00  60.00   70
 37  \w    103.00 178.00   1.00   24.58    --  112.00  77.00 -90.00   75
 38  \w     61.00 146.00   1.00   24.58    --  112.00 178.00-120.00   85
 39  \w     61.00 146.00   1.00   24.58    --  112.00 178.00 -90.00   85
 40  \w     61.00 146.00   1.00   24.58    --  112.00 178.00  60.00   85
 41  \w     61.00 146.00   1.00   24.58    --  112.00 178.00  90.00   85
 42  \w     36.00 145.00   1.00   24.58    --  112.00 -77.00 150.00  109
 43  \w     40.00 141.00   1.00   24.58    --  112.00 -61.00   0.00  101
 44  \w   -113.00 -13.00   1.00    6.15    --  -41.19 -57.00  60.00  100
 45  \w   -115.00 -17.00   1.00    6.15    --  -41.19 -38.00 -60.00   98
 46  \w    -87.00  -6.00   1.00    6.15    --  -41.19 125.00  30.00   81
 47  \w   -113.00 -13.00   1.00    6.15    --  -41.19 -57.00 -90.00  100
 48  \w      8.00  42.00   1.00    6.15    --   41.19  80.00-170.14   34
 49  \w      6.00  32.00   1.00    6.15    --   41.19  85.00 138.05   26
 50  \w      6.00  32.00   1.00    6.15    --   41.19  85.00   1.00   26
 51  \w      6.00  32.00   1.00    6.15    --   41.19  85.00 -36.41   26
 52  \w      7.00  42.00   1.00    6.15    --   41.19  82.00-119.91   35
 53  \w     83.00 178.00   1.00   24.58    --  112.00  61.00-180.00   95
 54  \w     83.00 178.00   1.00   24.58    --  112.00  61.00 -60.00   95
 55  \w     83.00 178.00   1.00   24.58    --  112.00  61.00  90.00   95
 56  \w     83.00 178.00   1.00   24.58    --  112.00  61.00 -90.00   95
 57  \w     83.00 178.00   1.00   24.58    --  112.00  61.00 -30.00   95
 58  \w     83.00 178.00   1.00   24.58    --  112.00  61.00   0.00   95
;
_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      -0.1918492000
_diffrn_orient_matrix_UB_12      0.0393607000
_diffrn_orient_matrix_UB_13      -0.0036342000
_diffrn_orient_matrix_UB_21      -0.0524943000
_diffrn_orient_matrix_UB_22      -0.1010424000
_diffrn_orient_matrix_UB_23      0.1115790000
_diffrn_orient_matrix_UB_31      -0.0300954000
_diffrn_orient_matrix_UB_32      0.1583738000
_diffrn_orient_matrix_UB_33      0.0665216000
_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  0.0424
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21328
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.366
_diffrn_reflns_theta_min         3.729
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.346
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
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    1.351
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      1.195
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0632
_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^)+(0.1103P)^2^+0.2814P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1855
_refine_ls_wR_factor_ref         0.1921
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2798
_reflns_number_total             3209
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00621j2.cif
_cod_data_source_block           Str_1xHClO4
_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 '296-298 deg.C (decomp.)'. The value was changed to '570.1(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               7250803
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         'C14 H19 N2, Cl O4'
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.579
_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
 Cl1-O4 = Cl1-O2 = Cl1-O3 = Cl1-O5
 1.5 with sigma of 0.02
 Cl1-O4 \\sim Cl1-O2 \\sim Cl1-O3 \\sim Cl1-O5
 with sigma of 0.02
 O4-O3 \\sim O2-O5 \\sim O4-O5 \\sim O2-O3 \\sim O4-O2 \\sim O3-O5
 with sigma of 0.04
 Cl1-O4 \\sim Cl1-O8
 with sigma of 0.02
 Cl1-O2 \\sim Cl1-O6
 with sigma of 0.02
 Cl1-O3 \\sim Cl1-O9
 with sigma of 0.02
 Cl1-O5 \\sim Cl1-O7
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl1 \\sim O4 \\sim O2 \\sim O3 \\sim O5: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 Cl1, O4, O2, O3, O5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O8)=Sof(O7)=Sof(O6)=Sof(O9)=1-FVAR(1)
 Sof(O4)=Sof(O2)=Sof(O3)=Sof(O5)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C6(H6), C4(H4), C2(H2A), C7(H7), C3(H3)
6.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C)
;
_shelx_res_checksum              28506
_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 1.865
_oxdiff_exptl_absorpt_empirical_full_min 0.750