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_7159263
_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         'C19 H19 N3'
_chemical_formula_sum            'C19 H19 N3'
_chemical_formula_weight         289.37
_chemical_melting_point          378.6(5)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-21
_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                 95.8360(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.90120(10)
_cell_length_b                   11.66600(10)
_cell_length_c                   23.8047(2)
_cell_measurement_reflns_used    19218
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.4300
_cell_measurement_theta_min      3.7660
_cell_volume                     3011.63(5)
_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      100.01(10)
_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   -113.00 -13.00   1.00    1.00    --  -40.82 -57.00 -60.00  100
  2  \w    -65.00  33.00   1.00    1.00    --  -40.82  38.00-180.00   98
  3  \w    -65.00  33.00   1.00    1.00    --  -40.82  38.00  90.00   98
  4  \w    -87.00  -6.00   1.00    1.00    --  -40.82 125.00 150.00   81
  5  \w      4.00  30.00   1.00    1.00    --   40.82  89.00 -50.81   26
  6  \w     30.00 106.00   1.00    1.20    --  112.00 -95.00 120.00   76
  7  \w     30.00 106.00   1.00    1.20    --  112.00 -95.00 -30.00   76
  8  \w    104.00 178.00   1.00    1.20    --  112.00 111.00 150.00   74
  9  \w     36.00 109.00   1.00    1.20    --  112.00-111.00  60.00   73
 10  \w     61.00 146.00   1.00    1.20    --  112.00 178.00   0.00   85
 11  \w     30.00 106.00   1.00    1.20    --  112.00 -95.00 150.00   76
 12  \w     61.00 146.00   1.00    1.20    --  112.00 178.00  60.00   85
 13  \w     30.00 106.00   1.00    1.20    --  112.00 -95.00  90.00   76
 14  \w     34.00 139.00   1.00    1.20    --  112.00 -26.00-166.09  105
 15  \w     58.00 109.00   1.00    1.20    --  112.00-111.00 150.00   51
 16  \w     30.00  59.00   1.00    1.20    --  112.00 -95.00-120.00   29
 17  \w    105.00 165.00   1.00    1.20    --  112.00 111.00-150.00   60
 18  \w     45.00 105.00   1.00    1.20    --  112.00-111.00  30.00   60
 19  \w     61.00  92.00   1.00    1.20    --  112.00 178.00 -90.00   31
 20  \w    106.00 174.00   1.00    1.20    --  112.00  30.00 120.00   68
 21  \w     74.00 102.00   1.00    1.20    --  112.00-111.00 -30.00   28
 22  \w     80.00 109.00   1.00    1.20    --  112.00-111.00  90.00   29
 23  \w     80.00 138.00   1.00    1.20    --  112.00 178.00  30.00   58
 24  \w     40.00 115.00   1.00    1.20    --  112.00 -45.00 150.00   75
 25  \w     60.00  92.00   1.00    1.20    --  112.00  15.00  60.00   32
 26  \w    123.00 149.00   1.00    1.20    --  112.00  15.00  60.00   26
 27  \w     46.00  79.00   1.00    1.20    --  112.00-111.00-120.00   33
 28  \w     53.00  80.00   1.00    1.20    --  112.00 -95.00 -60.00   27
 29  \w     70.00  96.00   1.00    1.20    --  112.00 -26.00-136.32   26
 30  \w     32.00  94.00   1.00    1.20    --  112.00 -95.00-150.00   62
;
_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      -0.1056914000
_diffrn_orient_matrix_UB_12      0.0110399000
_diffrn_orient_matrix_UB_13      -0.0478267000
_diffrn_orient_matrix_UB_21      0.0178324000
_diffrn_orient_matrix_UB_22      0.1309846000
_diffrn_orient_matrix_UB_23      -0.0001450000
_diffrn_orient_matrix_UB_31      0.0933634000
_diffrn_orient_matrix_UB_32      -0.0124691000
_diffrn_orient_matrix_UB_33      -0.0440491000
_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  0.0206
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            32597
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.068
_diffrn_reflns_theta_min         3.733
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.281
_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    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.515
_exptl_crystal_size_mid          0.399
_exptl_crystal_size_min          0.295
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.00051(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   1.286
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         6278
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.286
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0603
_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^)+(0.0168P)^2^+3.2372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1305
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6154
_reflns_number_total             6278
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00286a2.cif
_cod_data_source_block           Structure-9
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '105-106 deg.C' was changed
to '378.6(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               7159263
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C19 H19 N3'
_shelx_estimated_absorpt_t_max   0.844
_shelx_estimated_absorpt_t_min   0.749
_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. Uiso/Uaniso restraints and constraints
Uanis(C32) \\sim Ueq, Uanis(C32A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N6A) = Uanis(N6)
Uanis(C31A) = Uanis(C31)
Uanis(C34) = Uanis(C30)
Uanis(C32A) = Uanis(C32)
3. Others
 Sof(H32A)=Sof(C31)=Sof(H31)=Sof(N6)=Sof(H32C)=1-FVAR(1)
 Sof(N6A)=Sof(C31A)=Sof(H31A)=Sof(H32)=Sof(H32B)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C31A(H31A), C7(H7), C27(H27), C12(H12), C8(H8), C26(H26), C3(H3), C2(H2),
 C21(H21), C22(H22), C32(H32), C32(H32A), C13(H13), C14(H14), C31(H31),
 C32A(H32B), C32A(H32C)
4.b Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C19(H19A,H19B,H19C), C16(H16A,H16B,H16C), C37(H37A,H37B,
 H37C), C35(H35A,H35B,H35C), C18(H18A,H18B,H18C), C36(H36A,H36B,H36C), C17(H17A,
 H17B,H17C)
;
_shelx_res_checksum              9258
_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 1.214
_oxdiff_exptl_absorpt_empirical_full_min 0.894