Synthesis, conformational stability and molecular structure of 4-aryl- and 4,5-diaryl-1,8-bis(dimethylamino)naphthalenes.
Filatova, Ekaterina A.; Ermolenko, Eugeny A.; Pozharskii, Alexander F.; Ozeryanskii, Valery A.; Demidov, Oleg P.; Chernyshev, Anatoly V.; Metelitsa, Anatoly V.; Gulevskaya, Anna V.; Organic & biomolecular chemistry 21 (2023) 3388–3401; doi:10.1039/d3ob00286a

data_7159264
_publ_section_title
;
 Synthesis, conformational stability and molecular structure of 4-aryl-
 and 4,5-diaryl-1,8-bis(dimethylamino)naphthalenes.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3388
_journal_page_last               3401
_journal_paper_doi               10.1039/d3ob00286a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'B F4, 1(C28 H31 N2)'
_chemical_formula_sum            'C28 H31 B F4 N2'
_chemical_formula_weight         482.36
_chemical_melting_point          543.1(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
_audit_creation_date             2022-04-25
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2023-02-22 deposited with the CCDC.	2023-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                78.2030(19)
_cell_angle_beta                 89.1878(17)
_cell_angle_gamma                76.9905(14)
_cell_formula_units_Z            4
_cell_length_a                   7.79528(12)
_cell_length_b                   15.4280(3)
_cell_length_c                   21.7637(6)
_cell_measurement_reflns_used    23764
_cell_measurement_temperature    100
_cell_measurement_theta_max      76.1590
_cell_measurement_theta_min      4.6010
_cell_volume                     2494.98(10)
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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    -88.00   4.00   1.00    3.12    --  -42.10 118.00 -46.00   92
  2  \w   -119.00 -50.00   1.00    3.12    --  -42.10-159.00  73.00   69
  3  \w   -114.00 -20.00   1.00    3.12    --  -42.10 159.00 106.00   94
  4  \w     18.00  94.00   1.00    3.12    --   42.10-118.00-132.00   76
  5  \w     72.00 118.00   1.00    3.12    --   42.10 159.00 106.00   46
  6  \w     42.00 120.00   1.00    3.12    --   42.10-159.00  73.00   78
  7  \w     42.00 140.00   1.00   12.46    --  112.00-159.00  73.00   98
  8  \w     98.00 178.00   1.00   12.46    --  112.00 118.00 -46.00   80
  9  \w     71.00 164.00   1.00   12.46    --  112.00 159.00 106.00   93
 10  \w     37.00 114.00   1.00   12.46    --  112.00-118.00-132.00   77
 11  \w   -116.00 -18.00   1.00    3.12    --  -42.10 -38.00  60.00   98
 12  \w    -67.00  32.00   1.00    3.12    --  -42.10  38.00-120.00   99
 13  \w     18.00 116.00   1.00    3.12    --   42.10  38.00 -30.00   98
 14  \w      1.00  83.00   1.00    3.12    --   42.10 -99.00  90.00   82
 15  \w     36.00 113.00   1.00   12.46    --  112.00-111.00  60.00   77
 16  \w     57.00 150.00   1.00   12.46    --  112.00 178.00  30.00   93
 17  \w     40.00 141.00   1.00   12.46    --  112.00 -61.00   0.00  101
 18  \w     57.00 150.00   1.00   12.46    --  112.00 178.00  60.00   93
 19  \w     84.00 178.00   1.00   12.46    --  112.00  30.00-180.00   94
 20  \w     36.00 113.00   1.00   12.46    --  112.00-111.00-120.00   77
 21  \w     39.00 142.00   1.00   12.46    --  112.00 -65.00 -90.68  103
 22  \w     86.00 178.00   1.00   12.46    --  112.00  45.00 120.00   92
 23  \w    119.00 160.00   1.00   12.46    --  112.00 111.00 -60.00   41
 24  \w     39.00  84.00   1.00   12.46    --  112.00 -95.00   0.00   45
 25  \w     79.00 105.00   1.00   12.46    --  112.00-111.00 120.00   26
 26  \w     62.00 115.00   1.00   12.46    --  112.00 178.00 150.00   53
 27  \w     38.00 113.00   1.00   12.46    --  112.00-111.00 -90.00   75
 28  \w     45.00  70.00   1.00   12.46    --  112.00 -95.00 150.00   25
 29  \w     83.00 109.00   1.00   12.46    --  112.00 -95.00 150.00   26
 30  \w    124.00 150.00   1.00   12.46    --  112.00 111.00 -30.00   26
 31  \w     85.00 113.00   1.00   12.46    --  112.00-111.00  90.00   28
 32  \w    112.00 138.00   1.00   12.46    --  112.00  30.00 120.00   26
 33  \w     87.00 146.00   1.00   12.46    --  112.00  61.00 120.00   59
 34  \w     42.00 137.00   1.00   12.46    --  112.00 -30.00-180.00   95
 35  \w     90.00 120.00   1.00   12.46    --  112.00  77.00  60.00   30
 36  \w    101.00 127.00   1.00   12.46    --  112.00  45.00   0.00   26
 37  \w     75.00 101.00   1.00   12.46    --  112.00 -61.00 150.00   26
 38  \w    116.00 141.00   1.00   12.46    --  112.00 -61.00 150.00   25
 39  \w    101.00 127.00   1.00   12.46    --  112.00 -77.00 -30.00   26
 40  \w     94.00 144.00   1.00   12.46    --  112.00 -77.00  60.00   50
 41  \w    101.00 138.00   1.00   12.46    --  112.00 111.00  30.00   37
 42  \w     67.00  93.00   1.00   12.46    --  112.00 -45.00 150.00   26
 43  \w     91.00 118.00   1.00   12.46    --  112.00 -77.00-150.00   27
 44  \w     72.00 113.00   1.00   12.46    --  112.00-111.00 150.00   41
 45  \w     69.00 108.00   1.00   12.46    --  112.00 178.00-120.00   39
 46  \w    136.00 168.00   1.00   12.46    --  112.00  30.00  90.00   32
 47  \w     46.00  72.00   1.00   12.46    --  112.00-111.00 120.00   26
 48  \w     80.00 141.00   1.00   12.46    --  112.00  77.00 150.00   61
 49  \w     55.00 107.00   1.00   12.46    --  112.00 -45.00 -90.00   52
 50  \w     31.00 100.00   1.00   12.46    --  112.00 -15.00 -90.00   69
 51  \w    112.00 165.00   1.00   12.46    --  112.00 -15.00 -90.00   53
 52  \w     42.00  68.00   1.00   12.46    --  112.00-111.00   0.00   26
 53  \w    117.00 142.00   1.00   12.46    --  112.00 111.00  60.00   25
 54  \w     59.00  88.00   1.00   12.46    --  112.00 178.00 -60.00   29
 55  \w     61.00  97.00   1.00   12.46    --  112.00 178.00   0.00   36
 56  \w     41.00  81.00   1.00   12.46    --  112.00 -45.00-180.00   40
 57  \w     84.00 119.00   1.00   12.46    --  112.00  61.00  30.00   35
 58  \w    128.00 154.00   1.00   12.46    --  112.00  50.00  59.90   26
 59  \w    102.00 128.00   1.00   12.46    --  112.00 -77.00 -60.00   26
 60  \w     81.00 107.00   1.00   12.46    --  112.00 -83.00 179.06   26
 61  \w     94.00 126.00   1.00   12.46    --  112.00  50.00  59.90   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17038
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.255
_diffrn_reflns_theta_min         3.990
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.471
_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    1.284
_exptl_crystal_description       plate
_exptl_crystal_F_000             1016
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.457
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0012(3)
_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   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     857
_refine_ls_number_reflns         17038
_refine_ls_number_restraints     726
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0488
_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^)+(0.1005P)^2^+0.0444P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1428
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14326
_reflns_number_total             17038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00286a2.cif
_cod_data_source_block           Structure-3b-HBF4
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '269-271 deg.C' was changed
to '543.1(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 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7159260--7159267.cif.
;
_cod_original_cell_volume        2494.98(9)
_cod_database_code               7159264
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.715
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5585(9)
 0.4415(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(C16A)=Sof(H16A)=Sof(C15A)=Sof(C14A)=
 Sof(H14A)=Sof(C13A)=Sof(H13A)=Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(C11)=Sof(C16)=Sof(H16)=Sof(C12)=Sof(H12)=Sof(C15)=Sof(C13)=Sof(H13)=
 Sof(C14)=Sof(H14)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(1)
 Sof(C42A)=Sof(H42A)=Sof(C43A)=Sof(H43A)=Sof(C44A)=Sof(H44A)=Sof(C68)=
 Sof(C40A)=Sof(H40A)=Sof(C41A)=Sof(C52A)=Sof(H52D)=Sof(H52E)=Sof(H52F)=1-FVAR(2)
 Sof(C39)=Sof(C40)=Sof(H40)=Sof(C41)=Sof(C42)=Sof(H42)=Sof(C44)=Sof(H44)=
 Sof(C43)=Sof(H43)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(H52C)=FVAR(2)
 Sof(F8A)=Sof(F7A)=Sof(F5A)=Sof(F6A)=1-FVAR(3)
 Sof(F6)=Sof(F7)=Sof(F5)=Sof(F8)=FVAR(3)
 Sof(F4A)=Sof(F2A)=Sof(F1A)=Sof(F3A)=1-FVAR(4)
 Sof(F1)=Sof(F3)=Sof(F2)=Sof(F4)=FVAR(4)
5.a Aromatic/amide H refined with riding coordinates:
 C36(H36), C2(H2), C8(H8), C30(H30), C3(H3), C35(H35), C31(H31), C46(H46),
 C7(H7), C18(H18), C48(H48), C22(H22), C16(H16), C40(H40), C50(H50), C12(H12),
 C20(H20), C49(H49), C21(H21), C42(H42), C44(H44), C13(H13), C43(H43), C14(H14),
  C12A(H12A), C16A(H16A), C14A(H14A), C13A(H13A), C42A(H42A), C43A(H43A),
 C44A(H44A), C40A(H40A)
5.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C54(H54A,H54B,H54C), C53(H53A,H53B,H53C), C26(H26A,H26B,
 H26C), C56(H56A,H56B,H56C), C27(H27A,H27B,H27C), C55(H55A,H55B,H55C), C28(H28A,
 H28B,H28C), C23(H23A,H23B,H23C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C),
 C24(H24A,H24B,H24C), C24A(H24D,H24E,H24F), C52A(H52D,H52E,H52F)
;
_shelx_res_checksum              38700
_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
;