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_7159267
_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
'C26 H27 N2, 0.333(B0.507 F2.014), 0.667(B F3.999), 0.333(B0.493 F1.986)'
_chemical_formula_sum            'C26 H27 B F4 N2'
_chemical_formula_weight         454.30
_chemical_melting_point          519.6(5)
_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             2022-03-14
_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                99.3630(10)
_cell_angle_beta                 95.4340(10)
_cell_angle_gamma                95.9060(10)
_cell_formula_units_Z            6
_cell_length_a                   7.86640(10)
_cell_length_b                   22.4348(4)
_cell_length_c                   22.6910(3)
_cell_measurement_reflns_used    25876
_cell_measurement_temperature    100.02(13)
_cell_measurement_theta_max      75.9090
_cell_measurement_theta_min      2.5490
_cell_volume                     3904.79(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_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    -87.00  -6.00   1.00    6.00    --  -40.82 125.00 -30.00   81
  2  \w    -65.00  33.00   1.00    6.00    --  -40.82  38.00 120.00   98
  3  \w   -113.00 -13.00   1.00    6.00    --  -40.82 -57.00-180.00  100
  4  \w    -69.00  32.00   1.00    6.00    --  -40.82  57.00 -30.00  101
  5  \w      6.00  82.00   1.00    6.00    --   40.82 -99.00 120.00   76
  6  \w    -21.00  73.00   1.00    6.00    --   40.82 -77.00-180.00   94
  7  \w     36.00 140.00   1.00   24.00    --  112.00 -30.00-120.00  104
  8  \w    103.00 178.00   1.00   24.00    --  112.00  77.00   0.00   75
  9  \w     33.00 146.00   1.00   24.00    --  112.00 -82.00 -60.51  113
 10  \w     36.00 109.00   1.00   24.00    --  112.00-111.00  90.00   73
 11  \w     36.00 140.00   1.00   24.00    --  112.00 -30.00-150.00  104
 12  \w     36.00 109.00   1.00   24.00    --  112.00-111.00-180.00   73
 13  \w     86.00 178.00   1.00   24.00    --  112.00  45.00-180.00   92
 14  \w     39.00 138.00   1.00   24.00    --  112.00 -45.00   0.00   99
 15  \w     36.00 145.00   1.00   24.00    --  112.00 -77.00  60.00  109
 16  \w    104.00 178.00   1.00   24.00    --  112.00 111.00 -60.00   74
 17  \w     30.00 106.00   1.00   24.00    --  112.00 -95.00-120.00   76
 18  \w     84.00 178.00   1.00   24.00    --  112.00  30.00 120.00   94
 19  \w     36.00 109.00   1.00   24.00    --  112.00-111.00 -30.00   73
 20  \w     30.00 106.00   1.00   24.00    --  112.00 -95.00  90.00   76
 21  \w    103.00 178.00   1.00   24.00    --  112.00  77.00  30.00   75
 22  \w     39.00  66.00   1.00   24.00    --  112.00 -77.00-120.00   27
 23  \w     37.00  64.00   1.00   24.00    --  112.00 -95.00-180.00   27
 24  \w     42.00 109.00   1.00   24.00    --  112.00-111.00  60.00   67
 25  \w     30.00  65.00   1.00   24.00    --  112.00 -15.00-150.00   35
 26  \w     42.00  76.00   1.00   24.00    --  112.00-111.00 150.00   34
 27  \w     83.00 109.00   1.00   24.00    --  112.00-111.00 150.00   26
 28  \w    110.00 138.00   1.00   24.00    --  112.00 111.00   0.00   28
 29  \w     51.00  78.00   1.00   24.00    --  112.00 -95.00   0.00   27
 30  \w     74.00 103.00   1.00   24.00    --  112.00 -95.00-150.00   29
 31  \w     73.00 109.00   1.00   24.00    --  112.00-111.00 -60.00   36
 32  \w    109.00 136.00   1.00   24.00    --  112.00 -77.00  30.00   27
 33  \w     52.00  89.00   1.00   24.00    --  112.00 -45.00-150.00   37
 34  \w    112.00 163.00   1.00   24.00    --  112.00  77.00  90.00   51
 35  \w     70.00 140.00   1.00   24.00    --  112.00 178.00 -30.00   70
 36  \w     89.00 128.00   1.00   24.00    --  112.00 -61.00-180.00   39
 37  \w     59.00 100.00   1.00   24.00    --  112.00 -77.00  30.00   41
 38  \w     36.00  82.00   1.00   24.00    --  112.00-111.00-120.00   46
 39  \w    107.00 132.00   1.00   24.00    --  112.00 111.00  30.00   25
 40  \w    130.00 177.00   1.00   24.00    --  112.00  77.00 -30.00   47
 41  \w     30.00  59.00   1.00   24.00    --  112.00 -95.00 -30.00   29
 42  \w    106.00 144.00   1.00   24.00    --  112.00 178.00-180.00   38
 43  \w    111.00 138.00   1.00   24.00    --  112.00 -61.00   0.00   27
 44  \w     41.00 109.00   1.00   24.00    --  112.00-111.00   0.00   68
 45  \w     42.00  71.00   1.00   24.00    --  112.00 -95.00-150.00   29
 46  \w    105.00 130.00   1.00   24.00    --  112.00 -77.00-120.00   25
 47  \w     38.00  65.00   1.00   24.00    --  112.00 -77.00 -30.00   27
 48  \w     86.00 113.00   1.00   24.00    --  112.00 -77.00 -30.00   27
 49  \w     80.00 109.00   1.00   24.00    --  112.00-111.00-150.00   29
 50  \w     69.00 107.00   1.00   24.00    --  112.00-111.00 -90.00   38
 51  \w     80.00 107.00   1.00   24.00    --  112.00-111.00  30.00   27
 52  \w    120.00 177.00   1.00   24.00    --  112.00  77.00 -60.00   57
 53  \w    116.00 146.00   1.00   24.00    --  112.00 178.00  60.00   30
 54  \w    119.00 144.00   1.00   24.00    --  112.00 178.00  90.00   25
 55  \w     74.00  96.00   1.00   24.00    --  112.00 178.00 120.00   22
;
_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      -0.1423779000
_diffrn_orient_matrix_UB_12      0.0009374000
_diffrn_orient_matrix_UB_13      0.0422031000
_diffrn_orient_matrix_UB_21      0.0049893000
_diffrn_orient_matrix_UB_22      0.0692927000
_diffrn_orient_matrix_UB_23      0.0032400000
_diffrn_orient_matrix_UB_31      -0.1377465000
_diffrn_orient_matrix_UB_32      -0.0106058000
_diffrn_orient_matrix_UB_33      -0.0548183000
_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  0.0385
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            72975
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.268
_diffrn_reflns_theta_min         4.023
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.467
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.159
_exptl_crystal_description       plate
_exptl_crystal_F_000             1428
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1142
_refine_ls_number_reflns         16174
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0573
_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^)+(0.0840P)^2^+1.5351P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1610
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13477
_reflns_number_total             16174
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00286a2.cif
_cod_data_source_block           Structure-3a-HBF4
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '246-247 deg.C' was changed
to '519.6(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 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7159260--7159267.cif.
;
_cod_database_code               7159267
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C26 H27 B F4 N2'
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.756
_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. Uiso/Uaniso restraints and constraints
Uanis(F18) \\sim Ueq, Uanis(F15) \\sim Ueq, Uanis(F8) \\sim Ueq, Uanis(F17)
\\sim Ueq, Uanis(F8A) \\sim Ueq, Uanis(F14) \\sim Ueq, Uanis(F13) \\sim Ueq,
Uanis(F6) \\sim Ueq, Uanis(F6A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(F11A) = Uanis(F11)
Uanis(C67A) = Uanis(C67)
Uanis(C15A) = Uanis(C15)
Uanis(C11A) = Uanis(C11) = Uanis(C62B) = Uanis(C62A)
Uanis(C12A) = Uanis(C12)
Uanis(C16A) = Uanis(C16)
3. Others
 Sof(F1A)=Sof(F3A)=Sof(B1A)=Sof(F4A)=Sof(F2A)=1-FVAR(1)
 Sof(F4)=Sof(F1)=Sof(B1)=Sof(F3)=Sof(F2)=FVAR(1)
 Sof(F10A)=Sof(F9A)=Sof(F11A)=1-FVAR(2)
 Sof(F9)=Sof(F10)=Sof(F11)=FVAR(2)
 Sof(C63A)=Sof(H63A)=Sof(C64A)=Sof(H64A)=Sof(C65A)=Sof(H65A)=Sof(C66A)=
 Sof(H66A)=Sof(C67A)=Sof(H67A)=1-FVAR(3)
 Sof(C63)=Sof(H63)=Sof(C64)=Sof(H64)=Sof(C65)=Sof(H65)=Sof(C66)=Sof(H66)=
 Sof(C67)=Sof(H67)=FVAR(3)
 Sof(C16A)=Sof(H16A)=Sof(C12A)=Sof(H12A)=Sof(C15A)=Sof(H15A)=Sof(C14A)=
 Sof(H14A)=Sof(C13A)=Sof(H13A)=1-FVAR(4)
 Sof(C16)=Sof(H16)=Sof(C12)=Sof(H12)=Sof(C15)=Sof(H15)=Sof(C14)=Sof(H14)=
 Sof(C13)=Sof(H13)=FVAR(4)
 Sof(C11A)=1-FVAR(5)
 Sof(C11)=FVAR(5)
 Sof(C62B)=1-FVAR(6)
 Sof(C62A)=FVAR(6)
4.a Aromatic/amide H refined with riding coordinates:
 C34(H34), C33(H33), C54(H54), C7(H7), C28(H28), C29(H29), C42(H42), C8(H8),
 C3(H3), C48(H48), C2(H2A), C38(H38), C44(H44), C22(H22), C41(H41), C40(H40),
 C47(H47), C60(H60), C39(H39), C69(H69), C16(H16), C73(H73), C71(H71), C70(H70),
  C59(H59), C45(H45), C18(H18), C46(H46), C72(H72), C12(H12), C21(H21),
 C19(H19), C20(H20), C15(H15), C14(H14), C13(H13), C63(H63), C64(H64), C65(H65),
  C66(H66), C67(H67), C63A(H63A), C64A(H64A), C65A(H65A), C66A(H66A),
 C67A(H67A), C16A(H16A), C12A(H12A), C15A(H15A), C14A(H14A), C13A(H13A)
4.b Idealised Me refined as rotating group:
 C78(H78A,H78B,H78C), C75(H75A,H75B,H75C), C76(H76A,H76B,H76C), C51(H51A,H51B,
 H51C), C26(H26A,H26B,H26C), C77(H77A,H77B,H77C), C52(H52A,H52B,H52C), C25(H25A,
 H25B,H25C), C49(H49A,H49B,H49C), C23(H23A,H23B,H23C), C50(H50A,H50B,H50C),
 C24(H24A,H24B,H24C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              19201
_shelx_fab_checksum              50083
_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 1.486
_oxdiff_exptl_absorpt_empirical_full_min 0.794