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_7159261
_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         'C28 H30 N2'
_chemical_formula_sum            'C28 H30 N2'
_chemical_formula_weight         394.54
_chemical_melting_point          428.6(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             2022-04-25
_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                90
_cell_angle_beta                 98.8830(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.47430(10)
_cell_length_b                   10.54700(10)
_cell_length_c                   12.44470(10)
_cell_measurement_reflns_used    17308
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.9540
_cell_measurement_theta_min      4.1900
_cell_volume                     1098.947(19)
_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 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  27.00-141.00  108
  2  \w   -119.00 -11.00   1.00    1.00    --  -42.10 -27.00  55.00  108
  3  \w    -35.00  73.00   1.00    1.00    --   42.10 -27.00  55.00  108
  4  \w     11.00 119.00   1.00    1.00    --   42.10  27.00-141.00  108
  5  \w     35.00 143.00   1.00    1.00    --  112.00 -27.00  55.00  108
  6  \w     81.00 178.00   1.00    1.00    --  112.00  27.00-141.00   97
  7  \w   -116.00 -18.00   1.00    1.00    --  -42.10 -38.00 150.00   98
  8  \w   -118.00 -10.00   1.00    1.00    --  -42.10 -77.00 -90.00  108
  9  \w   -115.00 -14.00   1.00    1.00    --  -42.10 -57.00 -30.00  101
 10  \w   -116.00 -18.00   1.00    1.00    --  -42.10 -38.00-120.00   98
 11  \w     23.00  98.00   1.00    1.00    --   42.10-125.00  60.00   75
 12  \w     14.00 115.00   1.00    1.00    --   42.10  57.00 -30.00  101
 13  \w     23.00  98.00   1.00    1.00    --   42.10-125.00-180.00   75
 14  \w     18.00 116.00   1.00    1.00    --   42.10  38.00 -90.00   98
 15  \w     79.00 178.00   1.00    1.00    --  112.00  77.00-150.00   99
 16  \w     79.00 178.00   1.00    1.00    --  112.00  77.00-120.00   99
 17  \w     83.00 178.00   1.00    1.00    --  112.00  61.00 -60.00   95
 18  \w     79.00 178.00   1.00    1.00    --  112.00  77.00 -30.00   99
 19  \w     36.00 113.00   1.00    1.00    --  112.00-111.00 -60.00   77
 20  \w     59.00 178.00   1.00    1.00    --  112.00  15.00 -30.00  119
 21  \w     79.00 178.00   1.00    1.00    --  112.00  77.00 -90.00   99
 22  \w     45.00  90.00   1.00    1.00    --  112.00 -45.00-150.00   45
 23  \w     84.00 110.00   1.00    1.00    --  112.00  61.00 -30.00   26
 24  \w     84.00 116.00   1.00    1.00    --  112.00  61.00 -90.00   32
 25  \w     84.00 126.00   1.00    1.00    --  112.00  61.00  30.00   42
 26  \w     86.00 116.00   1.00    1.00    --  112.00  30.00 -30.00   30
 27  \w     59.00  85.00   1.00    1.00    --  112.00-111.00-120.00   26
 28  \w     83.00 118.00   1.00    1.00    --  112.00  61.00-120.00   35
 29  \w    132.00 157.00   1.00    1.00    --  112.00  61.00-120.00   25
 30  \w     87.00 129.00   1.00    1.00    --  112.00  45.00 120.00   42
 31  \w    151.00 177.00   1.00    1.00    --  112.00  45.00 120.00   26
 32  \w     41.00  75.00   1.00    1.00    --  112.00 -61.00   0.00   34
 33  \w     88.00 114.00   1.00    1.00    --  112.00 -61.00   0.00   26
 34  \w     79.00 106.00   1.00    1.00    --  112.00  77.00 -12.85   27
 35  \w     39.00 113.00   1.00    1.00    --  112.00-111.00 -30.00   74
 36  \w     45.00 115.00   1.00    1.00    --  112.00 -84.00 140.95   70
 37  \w     83.00 136.00   1.00    1.00    --  112.00  61.00   0.00   53
 38  \w     80.00 173.00   1.00    1.00    --  112.00  77.00   0.00   93
 39  \w     79.00 106.00   1.00    1.00    --  112.00  77.00 -60.00   27
 40  \w     39.00  64.00   1.00    1.00    --  112.00-111.00 -90.00   25
 41  \w     79.00 113.00   1.00    1.00    --  112.00-111.00 -90.00   34
 42  \w    121.00 147.00   1.00    1.00    --  112.00 111.00 -60.00   26
 43  \w     88.00 177.00   1.00    1.00    --  112.00  45.00 150.00   89
 44  \w    132.00 158.00   1.00    1.00    --  112.00  45.00  30.00   26
 45  \w     31.00  81.00   1.00    1.00    --  112.00 -15.00-180.00   50
 46  \w     54.00  80.00   1.00    1.00    --  112.00-111.00   0.00   26
 47  \w     40.00  66.00   1.00    1.00    --  112.00-111.00  30.00   26
 48  \w     86.00 111.00   1.00    1.00    --  112.00  30.00 -60.00   25
 49  \w    137.00 177.00   1.00    1.00    --  112.00  30.00 -60.00   40
 50  \w     86.00 113.00   1.00    1.00    --  112.00  45.00  30.00   27
 51  \w     97.00 123.00   1.00    1.00    --  112.00  62.00   1.05   26
 52  \w     86.00 142.00   1.00    1.00    --  112.00  45.00 -30.00   56
 53  \w     86.00 113.00   1.00    1.00    --  112.00  45.00 -60.00   27
 54  \w     33.00  87.00   1.00    1.00    --  112.00 -95.00 120.00   54
;
_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      -0.1574565000
_diffrn_orient_matrix_UB_12      -0.0374517000
_diffrn_orient_matrix_UB_13      -0.0721412000
_diffrn_orient_matrix_UB_21      0.0723273000
_diffrn_orient_matrix_UB_22      0.0353643000
_diffrn_orient_matrix_UB_23      -0.1021882000
_diffrn_orient_matrix_UB_31      0.0618962000
_diffrn_orient_matrix_UB_32      -0.1367188000
_diffrn_orient_matrix_UB_33      -0.0066589000
_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  0.0201
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22153
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.271
_diffrn_reflns_theta_min         3.595
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.435
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.273
_exptl_crystal_size_min          0.258
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 1921 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.30(11)
_refine_ls_extinction_coef       0.0042(5)
_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   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4395
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0255
_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^)+(0.0352P)^2^+0.1517P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0662
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_full    0.911
_reflns_Friedel_fraction_max     0.903
_reflns_number_gt                4347
_reflns_number_total             4395
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00286a2.cif
_cod_data_source_block           Structure-3b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '155-156 deg.C' was changed
to '428.6(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_original_cell_volume        1098.946(19)
_cod_database_code               7159261
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C28 H30 N2'
_shelx_estimated_absorpt_t_max   0.877
_shelx_estimated_absorpt_t_min   0.806
_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:
 C2(H2), C23(H23), C8(H8), C16(H16), C20(H20), C7(H7), C3(H3), C18(H18),
 C25(H25), C27(H27), C19(H19), C26(H26)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C28(H28A,H28B,H28C), C21(H21A,H21B,
 H21C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              58076
_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 1.209
_oxdiff_exptl_absorpt_empirical_full_min 0.805