Synthesis and crystal structures of 4,4′-methylenebis(2,6-diethylaniline) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline)
Smirnov, Daniil E.; Morozov, Oleg S.; Afanasyeva, Ekaterina S.; Avdeev, Viktor V.; Acta Crystallographica Section E Crystallographic Communications 81 (2025) –; doi:10.1107/S2056989025000234

data_2023356
_publ_section_title
;
 Synthesis and crystal structures of
 4,4&#x2032;-methylenebis(2,6-diethylaniline) and
 4,4&#x2032;-methylenebis(3-chloro-2,6-diethylaniline)
;
_journal_coeditor_code           NY2009
_journal_issue                   2
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989025000234
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C21 H30 N2'
_chemical_formula_moiety         'C21 H30 N2'
_chemical_formula_sum            'C21 H30 N2'
_chemical_formula_weight         310.47
_chemical_name_common
;
4,4'-Methylenebis(2,6-diethylaniline)
;
_chemical_name_systematic
;
4,4'-(Methanediyl)bis(2,6-diethylaniline)
;
_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_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 102.4188(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9895(3)
_cell_length_b                   11.8589(3)
_cell_length_c                   17.6765(5)
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      69.56
_cell_measurement_theta_min      4.52
_cell_volume                     1840.32(9)
_computing_cell_refinement
;
APEX3 v.2017.3_0 (Bruker, 2016)
;
_computing_data_collection
;
APEX3 v.2017.3_0 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT v.8.38A (Bruker, 2016)
;
_computing_molecular_graphics
;
Olex2 1.3 (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
Olex2 1.3 (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
<i>SHELXL2019/3</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2014/5</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22931
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.564
_diffrn_reflns_theta_min         4.523
_diffrn_source                   'microfocus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.490
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.6389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.327
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3455
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0668P)^2^+0.8039P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1345
_reflns_number_gt                3212
_reflns_number_total             3455
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ny2009.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2023356
_shelx_estimated_absorpt_t_min   0.859
_shelx_estimated_absorpt_t_max   0.939
_shelx_hkl_checksum              32923
_shelx_res_checksum              2514