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_7159265
_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 H30 N2'
_chemical_formula_sum            'C34 H30 N2'
_chemical_formula_weight         466.60
_chemical_melting_point          471.6(5)
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-27
_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                 98.5100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.85600(10)
_cell_length_b                   18.3880(2)
_cell_length_c                   8.83630(10)
_cell_measurement_reflns_used    18071
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.7650
_cell_measurement_theta_min      4.7920
_cell_volume                     1262.40(3)
_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_temperature      100
_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 0.998
_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    -73.00  35.00   1.00    1.00    --  -42.10  27.00 165.00  108
  2  \w   -119.00 -11.00   1.00    1.00    --  -42.10 -27.00   3.00  108
  3  \w     11.00 119.00   1.00    1.00    --   42.10  27.00 165.00  108
  4  \w     81.00 178.00   1.00    1.00    --  112.00  27.00 165.00   97
  5  \w     35.00 143.00   1.00    1.00    --  112.00 -27.00   3.00  108
  6  \w   -118.00 -10.00   1.00    1.00    --  -42.10 -77.00 -90.00  108
  7  \w   -116.00 -18.00   1.00    1.00    --  -42.10 -38.00 150.00   98
  8  \w   -115.00 -14.00   1.00    1.00    --  -42.10 -57.00 -60.00  101
  9  \w   -115.00 -14.00   1.00    1.00    --  -42.10 -57.00 -90.00  101
 10  \w     23.00  98.00   1.00    1.00    --   42.10-125.00-180.00   75
 11  \w    -35.00  73.00   1.00    1.00    --   42.10 -27.00   3.00  108
 12  \w     23.00  98.00   1.00    1.00    --   42.10-125.00  30.00   75
 13  \w     79.00 178.00   1.00    1.00    --  112.00  77.00-139.77   99
 14  \w     86.00 178.00   1.00    1.00    --  112.00  48.00   9.70   92
 15  \w     30.00 110.00   1.00    1.00    --  112.00 -95.00 -30.00   80
 16  \w     79.00 178.00   1.00    1.00    --  112.00  77.00-150.00   99
 17  \w     30.00 110.00   1.00    1.00    --  112.00 -95.00 120.00   80
 18  \w     86.00 178.00   1.00    1.00    --  112.00  45.00 -60.00   92
 19  \w     83.00 178.00   1.00    1.00    --  112.00  61.00 -90.00   95
 20  \w     57.00 150.00   1.00    1.00    --  112.00 178.00  30.00   93
 21  \w     80.00 178.00   1.00    1.00    --  112.00  74.00 -65.90   98
 22  \w     79.00 178.00   1.00    1.00    --  112.00  77.00 -90.00   99
 23  \w     86.00 178.00   1.00    1.00    --  112.00  45.00  60.00   92
 24  \w     79.00 178.00   1.00    1.00    --  112.00  77.00 -30.00   99
 25  \w     84.00 110.00   1.00    1.00    --  112.00 -95.00 -90.00   26
 26  \w     65.00  92.00   1.00    1.00    --  112.00 -15.00 120.00   27
 27  \w     80.00 105.00   1.00    1.00    --  112.00  77.00 -60.00   25
 28  \w    122.00 177.00   1.00    1.00    --  112.00  77.00 -60.00   55
 29  \w     37.00  64.00   1.00    1.00    --  112.00 -95.00  30.00   27
 30  \w     85.00 110.00   1.00    1.00    --  112.00  30.00 -30.00   25
 31  \w     79.00 106.00   1.00    1.00    --  112.00  77.00-120.00   27
 32  \w     51.00 105.00   1.00    1.00    --  112.00 -95.00-180.00   54
 33  \w     68.00  95.00   1.00    1.00    --  112.00 -61.00 150.00   27
 34  \w     86.00 113.00   1.00    1.00    --  112.00  45.00 -90.00   27
 35  \w    141.00 168.00   1.00    1.00    --  112.00  61.00-150.00   27
 36  \w    100.00 141.00   1.00    1.00    --  112.00 -61.00 150.00   41
 37  \w     86.00 115.00   1.00    1.00    --  112.00  45.00-120.00   29
 38  \w     88.00 135.00   1.00    1.00    --  112.00  45.00 -30.00   47
 39  \w     86.00 140.00   1.00    1.00    --  112.00  30.00-120.00   54
 40  \w     87.00 114.00   1.00    1.00    --  112.00  61.00-120.00   27
 41  \w     83.00 110.00   1.00    1.00    --  112.00  61.00 -60.00   27
 42  \w     84.00 111.00   1.00    1.00    --  112.00  61.00-180.00   27
 43  \w    120.00 147.00   1.00    1.00    --  112.00  77.00-180.00   27
 44  \w     85.00 112.00   1.00    1.00    --  112.00  77.00-180.00   27
 45  \w     41.00  66.00   1.00    1.00    --  112.00 -61.00-150.00   25
 46  \w     84.00 111.00   1.00    1.00    --  112.00 -61.00-150.00   27
 47  \w     84.00 111.00   1.00    1.00    --  112.00  61.00-150.00   27
 48  \w    127.00 153.00   1.00    1.00    --  112.00 -15.00 120.00   26
 49  \w     58.00  85.00   1.00    1.00    --  112.00-111.00 150.00   27
 50  \w     86.00 113.00   1.00    1.00    --  112.00  45.00-150.00   27
 51  \w     97.00 149.00   1.00    1.00    --  112.00 178.00 -90.00   52
 52  \w    106.00 133.00   1.00    1.00    --  112.00 178.00   0.00   27
 53  \w    133.00 171.00   1.00    1.00    --  112.00  30.00 -90.00   38
 54  \w     89.00 127.00   1.00    1.00    --  112.00  30.00 -60.00   38
 55  \w     84.00 115.00   1.00    1.00    --  112.00  61.00 -30.00   31
 56  \w     35.00 103.00   1.00    1.00    --  112.00 -95.00  60.00   68
 57  \w    -42.00 -17.00   1.00    1.00    --  -41.60  27.00 165.00   25
 58  \w     41.00  67.00   1.00    1.00    --  112.00 -95.00 -60.00   26
 59  \w     80.00 106.00   1.00    1.00    --  112.00 178.00 150.00   26
 60  \w    110.00 136.00   1.00    1.00    --  112.00 178.00 150.00   26
 61  \w     83.00 109.00   1.00    1.00    --  112.00  61.00-180.00   26
 62  \w    127.00 153.00   1.00    1.00    --  112.00  61.00-180.00   26
 63  \w     85.00 137.00   1.00    1.00    --  112.00  77.00   0.00   52
 64  \w     48.00  74.00   1.00    1.00    --  112.00-111.00 -90.00   26
 65  \w     87.00 113.00   1.00    1.00    --  112.00  45.00 -60.00   26
 66  \w    137.00 163.00   1.00    1.00    --  112.00  30.00-180.00   26
 67  \w     92.00 118.00   1.00    1.00    --  112.00  30.00 -90.00   26
 68  \w    103.00 129.00   1.00    1.00    --  112.00  30.00 120.00   26
 69  \w     83.00 109.00   1.00    1.00    --  112.00  61.00-150.00   26
 70  \w     76.00 102.00   1.00    1.00    --  112.00 -70.00 -17.09   26
 71  \w     72.00  98.00   1.00    1.00    --  112.00 -15.00 -90.00   26
 72  \w     60.00  86.00   1.00    1.00    --  112.00-111.00-120.00   26
;
_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      -0.1981970000
_diffrn_orient_matrix_UB_12      0.0026812000
_diffrn_orient_matrix_UB_13      -0.0272432000
_diffrn_orient_matrix_UB_21      0.0035739000
_diffrn_orient_matrix_UB_22      0.0301548000
_diffrn_orient_matrix_UB_23      -0.1621497000
_diffrn_orient_matrix_UB_31      -0.0055804000
_diffrn_orient_matrix_UB_32      -0.0781070000
_diffrn_orient_matrix_UB_33      -0.0635903000
_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  0.0264
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            28780
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.198
_diffrn_reflns_theta_min         4.810
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.340
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.197
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2232 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.28(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5043
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.2159P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0808
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.922
_reflns_Friedel_fraction_max     0.916
_reflns_number_gt                4937
_reflns_number_total             5043
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00286a2.cif
_cod_data_source_block           Structure-3d
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '198-199 deg.C' was changed
to '471.6(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               7159265
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C34 H30 N2'
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.820
_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:
 C7(H7), C27(H27), C3(H3), C8(H8), C34(H34), C2(H2), C24(H24), C32(H32),
 C16(H16), C26(H26), C22(H22), C29(H29), C17(H17), C19(H19), C20(H20), C31(H31),
  C30(H30), C21(H21)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C11(H11A,H11B,
 H11C)
;
_shelx_res_checksum              73704
_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 1.292
_oxdiff_exptl_absorpt_empirical_full_min 0.832