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_2023357
_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_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 H28 Cl2 N2'
_chemical_formula_moiety         'C21 H28 Cl2 N2'
_chemical_formula_sum            'C21 H28 Cl2 N2'
_chemical_formula_weight         379.35
_chemical_name_common
;
4,4'-Methylenebis(3-chloro-2,6-diethylaniline)
;
_chemical_name_systematic
;
4,4'-(MethAnediyl)bis(3-chloro-2,6-diethylaniline)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                69.352(11)
_cell_angle_beta                 77.257(12)
_cell_angle_gamma                87.670(8)
_cell_formula_units_Z            2
_cell_length_a                   8.993(3)
_cell_length_b                   9.6540(13)
_cell_length_c                   12.216(4)
_cell_measurement_reflns_used    5979
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.985
_cell_measurement_theta_min      1.674
_cell_volume                     967.2(5)
_computing_cell_refinement
;
<i>XDS</i> (Kabsch, 2010)
;
_computing_data_collection
;
<i>Marccd</i> (Doyle, 2011)
;
_computing_data_reduction
;
<i>XDS</i> (Kabsch, 2010)
;
_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      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       \f
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.75268
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17607
_diffrn_reflns_theta_full        26.847
_diffrn_reflns_theta_max         30.520
_diffrn_reflns_theta_min         2.390
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.001
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
[<i>XDS</i> (Kabsch, 2010)]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       plate
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.558
_refine_ls_extinction_coef       0.090(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2019/2 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0506
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0847P)^2^+0.2296P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1471
_reflns_number_gt                3879
_reflns_number_total             4844
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ny2009.cif
_cod_data_source_block           2
_cod_database_code               2023357
_shelx_estimated_absorpt_t_min   0.928
_shelx_estimated_absorpt_t_max   0.980
_shelx_hkl_checksum              9855
_shelx_res_checksum              78341