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_7159262
_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         'C34 H31 N2, 1(B F4)'
_chemical_formula_sum            'C34 H31 B F4 N2'
_chemical_formula_weight         554.42
_chemical_melting_point          'decomposed above 300 deg.C'
_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             2022-03-24
_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                90
_cell_angle_beta                 98.224(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.6368(5)
_cell_length_b                   7.90950(10)
_cell_length_c                   15.4739(3)
_cell_measurement_reflns_used    13326
_cell_measurement_temperature    100.02(13)
_cell_measurement_theta_max      75.8220
_cell_measurement_theta_min      5.8300
_cell_volume                     2742.05(9)
_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 0.998
_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    6.43    --  -40.82 125.00   0.00   81
  2  \w   -115.00 -16.00   1.00    6.43    --  -40.82 -38.00 150.00   99
  3  \w    -87.00  -6.00   1.00    6.43    --  -40.82 125.00  90.00   81
  4  \w      8.00  42.00   1.00    6.43    --   40.82  78.00 141.80   34
  5  \w      6.00  82.00   1.00    6.43    --   40.82 -99.00   0.00   76
  6  \w      4.00  30.00   1.00    6.43    --   40.82  89.00 -92.45   26
  7  \w    104.00 178.00   1.00   25.72    --  112.00 111.00  30.00   74
  8  \w    103.00 178.00   1.00   25.72    --  112.00  77.00-180.00   75
  9  \w     39.00 138.00   1.00   25.72    --  112.00 -45.00-180.00   99
 10  \w     61.00 146.00   1.00   25.72    --  112.00 178.00-120.00   85
 11  \w     83.00 178.00   1.00   25.72    --  112.00  61.00  60.00   95
 12  \w     84.00 178.00   1.00   25.72    --  112.00  30.00 -90.00   94
 13  \w     38.00 137.00   1.00   25.72    --  112.00 -39.00 106.54   99
 14  \w    104.00 178.00   1.00   25.72    --  112.00 111.00  60.00   74
 15  \w     83.00 178.00   1.00   25.72    --  112.00  61.00 120.00   95
 16  \w     86.00 178.00   1.00   25.72    --  112.00  45.00-150.00   92
 17  \w    103.00 178.00   1.00   25.72    --  112.00  77.00 150.00   75
 18  \w     36.00 109.00   1.00   25.72    --  112.00-111.00  30.00   73
 19  \w     39.00 136.00   1.00   25.72    --  112.00 -45.00   0.00   97
 20  \w     62.00 145.00   1.00   25.72    --  112.00 178.00  30.00   83
 21  \w    126.00 153.00   1.00   25.72    --  112.00  30.00  60.00   27
 22  \w     37.00  62.00   1.00   25.72    --  112.00-111.00 -90.00   25
 23  \w     54.00 140.00   1.00   25.72    --  112.00 -30.00 -30.00   86
 24  \w     37.00  74.00   1.00   25.72    --  112.00-111.00-150.00   37
 25  \w    123.00 150.00   1.00   25.72    --  112.00  77.00 120.00   27
 26  \w     31.00  58.00   1.00   25.72    --  112.00 -95.00 -90.00   27
 27  \w     40.00  67.00   1.00   25.72    --  112.00 -77.00 -30.00   27
;
_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      0.0653245000
_diffrn_orient_matrix_UB_12      0.0608844000
_diffrn_orient_matrix_UB_13      0.0132106000
_diffrn_orient_matrix_UB_21      -0.0104878000
_diffrn_orient_matrix_UB_22      0.0931857000
_diffrn_orient_matrix_UB_23      0.0838764000
_diffrn_orient_matrix_UB_31      0.0187180000
_diffrn_orient_matrix_UB_32      -0.1598184000
_diffrn_orient_matrix_UB_33      0.0539768000
_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  0.0417
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29400
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.222
_diffrn_reflns_theta_min         3.946
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.618
_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    1.343
_exptl_crystal_description       plate
_exptl_crystal_F_000             1160
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile/dichloromethane'
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.137
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         5710
_refine_ls_number_restraints     679
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.1039
_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^)+(0.1720P)^2^+4.5376P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3147
_refine_ls_wR_factor_ref         0.3205
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5044
_reflns_number_total             5710
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00286a2.cif
_cod_data_source_block           Structure-3c-HBF4
_cod_depositor_comments
'Adding full bibliography for 7159260--7159267.cif.'
_cod_original_cell_volume        2742.04(9)
_cod_database_code               7159262
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C34 H31 B F4 N2'
_shelx_estimated_absorpt_t_max   0.899
_shelx_estimated_absorpt_t_min   0.811
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 B2-F3 = B2-F4 = B2-F5 = B2-F6
 1.42 with sigma of 0.02
 B1-F1 = B1-F2 = B1-F7 = B1-F8
 1.42 with sigma of 0.02
 B3-F9 = B3-F10 = B3-F11 = B3-F12
 1.42 with sigma of 0.02
 C29-C30 \\sim C29A-C30A
 with sigma of 0.02
 C6-C34 \\sim C6-C34A
 with sigma of 0.04
 C26-C27 \\sim C26A-C27A
 with sigma of 0.02
 C26-C25 \\sim C26A-C25A
 with sigma of 0.02
 C27-C28 \\sim C27A-C28A
 with sigma of 0.02
 C6-C25 \\sim C6-C25A
 with sigma of 0.02
 C25-C34 \\sim C25A-C34A
 with sigma of 0.02
 C29-C34 \\sim C29A-C34A
 with sigma of 0.02
 C29-C28 \\sim C29A-C28A
 with sigma of 0.02
 C34-C33 \\sim C34A-C33A
 with sigma of 0.02
 C34-C30 \\sim C34A-C30A
 with sigma of 0.04
 C32-C30 \\sim C32A-C30A
 with sigma of 0.04
 C32-C33 \\sim C32A-C33A
 with sigma of 0.02
 C32-C31 \\sim C32A-C31A
 with sigma of 0.02
 C25-C33 \\sim C25A-C33A
 with sigma of 0.04
 C34-C32 \\sim C34A-C32A
 with sigma of 0.04
 C34-C28 \\sim C34A-C28A
 with sigma of 0.04
 C30-C31 \\sim C30A-C31A
 with sigma of 0.02
 C29-C27 \\sim C29A-C27A
 with sigma of 0.04
 C29-C25 \\sim C29A-C25A
 with sigma of 0.04
 C29-C33 \\sim C29A-C33A
 with sigma of 0.04
 C33-C31 \\sim C33A-C31A
 with sigma of 0.04
 C29-C31 \\sim C29A-C31A
 with sigma of 0.04
 C28-C30 \\sim C28A-C30A
 with sigma of 0.04
 C26-C6 \\sim C26A-C6
 with sigma of 0.04
 C26-C34 \\sim C26A-C34A
 with sigma of 0.04
 C26-C28 \\sim C26A-C28A
 with sigma of 0.04
 C27-C25 \\sim C27A-C25A
 with sigma of 0.04
 F3-F4 \\sim F4-F5 \\sim F5-F6 \\sim F6-F3 \\sim F4-F6 \\sim F3-F5
 with sigma of 0.04
 B2-F3 \\sim B2-F4 \\sim B2-F5 \\sim B2-F6
 with sigma of 0.02
 B1-F1 \\sim B1-F2 \\sim B1-F7 \\sim B1-F8
 with sigma of 0.02
 F1-F2 \\sim F2-F7 \\sim F7-F8 \\sim F8-F1 \\sim F2-F8 \\sim F1-F7
 with sigma of 0.04
 F9-F10 \\sim F10-F11 \\sim F11-F12 \\sim F12-F9 \\sim F10-F12 \\sim F9-F11
 with sigma of 0.04
 B3-F9 \\sim B3-F10 \\sim B3-F11 \\sim B3-F12
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
B2 \\sim F3 \\sim F4 \\sim F5 \\sim F6: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
B1 \\sim F1 \\sim F2 \\sim F7 \\sim F8: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
B3 \\sim F9 \\sim F10 \\sim F11 \\sim F12: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
Uanis(C7) = Uanis(C7A)
Uanis(C29A) = Uanis(C29)
Uanis(C28A) = Uanis(C31A)
Uanis(C30A) = Uanis(C30)
Uanis(C32A) = Uanis(C27)
Uanis(C27A) = Uanis(C27)
Uanis(C31A) = Uanis(C31)
Uanis(C28A) = Uanis(C28)
Uanis(C33A) = Uanis(C26A)
4. 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
5. Others
 Sof(H8B)=Sof(C7A)=Sof(H7A)=Sof(C6A)=1-FVAR(1)
 Sof(H8A)=Sof(C6)=Sof(C7)=Sof(H7)=FVAR(1)
 Sof(C25A)=Sof(C34A)=Sof(C33A)=Sof(H33A)=Sof(C32A)=Sof(H32A)=Sof(C31A)=
 Sof(H31A)=Sof(C30A)=Sof(H30A)=Sof(C29A)=Sof(C28A)=Sof(H28A)=Sof(C27A)=
 Sof(H27A)=Sof(C26A)=Sof(H26A)=1-FVAR(2)
 Sof(C29)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=Sof(C25)=Sof(C34)=Sof(C32)=
 Sof(H32)=Sof(C33)=Sof(H33)=Sof(C28)=Sof(H28)=Sof(C30)=Sof(H30)=Sof(C31)=
 Sof(H31)=FVAR(2)
 Fixed Sof: B2(0.33333) F3(0.33333) F4(0.33333) F5(0.33333) F6(0.33333)
 B1(0.33333) F1(0.33333) F2(0.33333) F7(0.33333) F8(0.33333) B3(0.33333)
 F9(0.33333) F10(0.33333) F11(0.33333) F12(0.33333)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C16(H16), C17(H17), C8(H8A), C8(H8B), C18(H18), C3(H3), C20(H20),
 C23(H23), C26(H26), C22(H22), C27(H27), C21(H21), C7(H7), C32(H32), C33(H33),
 C28(H28), C30(H30), C31(H31), C7A(H7A), C33A(H33A), C32A(H32A), C31A(H31A),
 C30A(H30A), C28A(H28A), C27A(H27A), C26A(H26A)
6.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C)
;
_shelx_res_checksum              86780
_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 1.913
_oxdiff_exptl_absorpt_empirical_full_min 0.748