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_7159260
_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 H26 N2'
_chemical_formula_sum            'C26 H26 N2'
_chemical_formula_weight         366.49
_chemical_melting_point          434.6(5)
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-15
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.01180(10)
_cell_length_b                   12.18120(10)
_cell_length_c                   13.61280(10)
_cell_measurement_reflns_used    9415
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.8700
_cell_measurement_theta_min      3.6010
_cell_volume                     1991.80(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_environment      N~2~
_diffrn_ambient_temperature      100.00(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   -129.00  47.00   1.00    1.00    --  -40.82   0.00-150.00  176
  2  \w      5.00  31.00   1.00    1.00    --   40.82  87.00-100.81   26
  3  \w     36.00 109.00   1.00    1.00    --  112.00-111.00 150.00   73
  4  \w     83.00 178.00   1.00    1.00    --  112.00  61.00 -90.00   95
  5  \w     39.00 138.00   1.00    1.00    --  112.00 -47.00   6.00   99
  6  \w     36.00 109.00   1.00    1.00    --  112.00-111.00-150.00   73
  7  \w     86.00 178.00   1.00    1.00    --  112.00  45.00-180.00   92
  8  \w     30.00 106.00   1.00    1.00    --  112.00 -95.00  60.00   76
  9  \w     84.00 117.00   1.00    1.00    --  112.00  61.00 -60.00   33
 10  \w    128.00 167.00   1.00    1.00    --  112.00  61.00 -60.00   39
 11  \w    131.00 157.00   1.00    1.00    --  112.00  77.00-120.00   26
 12  \w     34.00  77.00   1.00    1.00    --  112.00-104.00 -82.00   43
 13  \w    143.00 169.00   1.00    1.00    --  112.00 111.00  90.00   26
 14  \w    111.00 178.00   1.00    1.00    --  112.00 111.00  30.00   67
 15  \w    132.00 158.00   1.00    1.00    --  112.00  77.00-150.00   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      -0.0115929000
_diffrn_orient_matrix_UB_12      -0.1030562000
_diffrn_orient_matrix_UB_13      -0.0647805000
_diffrn_orient_matrix_UB_21      -0.0731884000
_diffrn_orient_matrix_UB_22      0.0649793000
_diffrn_orient_matrix_UB_23      -0.0725213000
_diffrn_orient_matrix_UB_31      0.1046916000
_diffrn_orient_matrix_UB_32      0.0339883000
_diffrn_orient_matrix_UB_33      -0.0578545000
_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  0.0165
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11906
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.016
_diffrn_reflns_theta_min         4.872
_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  0.195
_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    1.222
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.454
_exptl_crystal_size_mid          0.381
_exptl_crystal_size_min          0.255
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1684 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(13)
_refine_ls_extinction_coef       0.0024(3)
_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   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0270
_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^)+(0.0365P)^2^+0.3186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0716
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                4034
_reflns_number_total             4090
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00286a2.cif
_cod_data_source_block           Structure-3a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '161-162 deg.C' was changed
to '434.6(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               7159260
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C26 H26 N2'
_shelx_estimated_absorpt_t_max   0.874
_shelx_estimated_absorpt_t_min   0.791
_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), C22(H22), C3(H3), C2(H2), C8(H8), C23(H23), C26(H26), C16(H16),
 C20(H20), C25(H25), C24(H24), C19(H19), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C11(H11A,H11B,H11C), C13(H13A,H13B,
 H13C)
;
_shelx_res_checksum              47183
_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 1.225
_oxdiff_exptl_absorpt_empirical_full_min 0.778