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#$Date: 2025-08-20 22:19:29 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301836 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/98/4309843.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4309843
loop_
_publ_author_name
'Neil Burford'
'T. Stanley Cameron'
'Charles L. B. Macdonald'
'Katherine N. Robertson'
'Robert Schurko'
'Denise Walsh'
'Robert McDonald'
'Roderick E. Wasylishen'
_publ_contact_author_address
;
Department of Chemistry
Dalhousie University
Halifax, Nova Scotia
B3H 4J3
Canada
;
_publ_contact_author_email       ' neil.burford@dal.ca '
_publ_contact_author_fax         ' (902) 494-1310 '
_publ_contact_author_name        ' Neil Burford'
_publ_contact_author_phone       ' (902) 494-3190 '
_publ_section_title
;
Dissociation of
2,4-Bis(2,4,6-tri-tert-butylphenyl)-cyclo-1,3-dipnicta-2,4-diazanes (pnict
= P, As, Sb) Imposed by Substituent Steric Strain: A Cyclobutane/Olefin
Analogy
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              8058
_journal_page_last               8064
_journal_paper_doi               10.1021/ic050770h
_journal_volume                  44
_journal_year                    2005
_chemical_formula_moiety         'C36 H58 As2 Cl2 N2 '
_chemical_formula_sum            'C36 H58 As2 Cl2 N2'
_chemical_formula_weight         739.62
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 113.66(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.397(7)
_cell_length_b                   17.611(6)
_cell_length_c                   11.442(7)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      18.2
_cell_measurement_theta_min      15.0
_cell_volume                     1919(2)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction
;
teXsan for Windows version 1.06 (MSC, 1997-1999)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
SIR97 (Altomare, et. al. 1997)
;
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device       'Rigaku AFC5R'
_diffrn_measurement_method       ω-2θ
_diffrn_orient_matrix_UB_11      -0.05606
_diffrn_orient_matrix_UB_12      -0.02396
_diffrn_orient_matrix_UB_13      0.04360
_diffrn_orient_matrix_UB_21      0.00391
_diffrn_orient_matrix_UB_22      -0.04982
_diffrn_orient_matrix_UB_23      -0.04037
_diffrn_orient_matrix_UB_31      0.08871
_diffrn_orient_matrix_UB_32      -0.01295
_diffrn_orient_matrix_UB_33      0.07465
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.04973
_diffrn_reflns_av_sigmaI/netI    0.178
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3493
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        -5.08
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.906
_exptl_absorpt_correction_T_max  0.8323
_exptl_absorpt_correction_T_min  0.5987
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North,Phillips & Mathews, 1968
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             776.00
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.621
_refine_diff_density_min         -1.161
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3165
_refine_ls_number_restraints     112
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.2660
_refine_ls_R_factor_gt           0.0554
_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/[σ²(Fo²)+(0.0000P)²+18.9382P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1738
_reflns_number_gt                1158
_reflns_number_total             3165
_reflns_threshold_expression     I>2.00σ(I)
_cod_data_source_file            ic050770hsi20050513_022640_3.cif
_cod_data_source_block           '[Mes*NAsCl]2'
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_original_formula_sum        'C36 H58 As2 Cl2 N2 '
_cod_database_code               4309843
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
As1 As 0.45996(12) 0.03687(6) -0.11896(11) 0.0238(3) Uani 1 1 d U . .
Cl1 Cl 0.6153(4) 0.00414(18) -0.1998(3) 0.0446(9) Uani 1 1 d U . .
N1 N 0.5743(8) 0.0524(4) 0.0502(7) 0.0180(19) Uani 1 1 d U . .
C1 C 0.6788(9) 0.1135(5) 0.0812(9) 0.018(2) Uani 1 1 d DU . .
C2 C 0.8259(9) 0.1005(5) 0.1336(10) 0.023(2) Uani 1 1 d DU . .
C3 C 0.9120(10) 0.1553(5) 0.1171(9) 0.022(2) Uani 1 1 d DU . .
H3 H 1.0038 0.1370 0.1403 0.027 Uiso 1 1 d R . .
C4 C 0.8638(9) 0.2245(5) 0.0587(10) 0.023(2) Uani 1 1 d DU . .
C5 C 0.7229(9) 0.2389(5) 0.0280(9) 0.022(2) Uani 1 1 d DU . .
H5 H 0.7001 0.2876 -0.0078 0.026 Uiso 1 1 d R . .
C6 C 0.6295(9) 0.1876(4) 0.0445(9) 0.015(2) Uani 1 1 d DU . .
C7 C 0.8945(9) 0.0285(6) 0.2134(9) 0.030(2) Uani 1 1 d DU . .
C8 C 0.9641(10) 0.2802(5) 0.0340(9) 0.025(2) Uani 1 1 d DU . .
C9 C 0.4873(10) 0.2233(5) 0.0302(8) 0.019(2) Uani 1 1 d DU . .
C10 C 0.8401(12) 0.0210(6) 0.3211(10) 0.039(3) Uani 1 1 d DU . .
H10A H 0.8790 -0.0245 0.3706 0.059 Uiso 1 1 calc R . .
H10B H 0.7384 0.0176 0.2836 0.059 Uiso 1 1 calc R . .
H10C H 0.8688 0.0651 0.3764 0.059 Uiso 1 1 calc R . .
C11 C 0.8637(12) -0.0432(6) 0.1294(10) 0.040(3) Uani 1 1 d DU . .
H11A H 0.7652 -0.0440 0.0720 0.060 Uiso 1 1 calc R . .
H11B H 0.8856 -0.0880 0.1833 0.060 Uiso 1 1 calc R . .
H11C H 0.9209 -0.0428 0.0802 0.060 Uiso 1 1 calc R . .
C12 C 1.0552(9) 0.0346(7) 0.2820(11) 0.045(3) Uani 1 1 d DU . .
H12A H 1.0795 0.0796 0.3353 0.068 Uiso 1 1 calc R . .
H12B H 1.0959 0.0380 0.2193 0.068 Uiso 1 1 calc R . .
H12C H 1.0915 -0.0101 0.3347 0.068 Uiso 1 1 calc R . .
C13 C 1.0120(13) 0.2422(7) -0.0628(11) 0.049(4) Uani 1 1 d DU . .
H13A H 1.0874 0.2717 -0.0699 0.073 Uiso 1 1 calc R . .
H13B H 0.9337 0.2397 -0.1454 0.073 Uiso 1 1 calc R . .
H13C H 1.0453 0.1913 -0.0341 0.073 Uiso 1 1 calc R . .
C14 C 1.0921(11) 0.2950(7) 0.1568(10) 0.037(3) Uani 1 1 d DU . .
H14A H 1.1377 0.2471 0.1915 0.056 Uiso 1 1 calc R . .
H14B H 1.0630 0.3195 0.2181 0.056 Uiso 1 1 calc R . .
H14C H 1.1572 0.3277 0.1391 0.056 Uiso 1 1 calc R . .
C15 C 0.8923(12) 0.3552(6) -0.0230(13) 0.048(4) Uani 1 1 d DU . .
H15A H 0.8111 0.3453 -0.1014 0.073 Uiso 1 1 calc R . .
H15B H 0.9576 0.3875 -0.0409 0.073 Uiso 1 1 calc R . .
H15C H 0.8625 0.3804 0.0373 0.073 Uiso 1 1 calc R . .
C16 C 0.5181(11) 0.3003(5) 0.0993(10) 0.026(3) Uani 1 1 d DU . .
H16A H 0.5804 0.2928 0.1881 0.039 Uiso 1 1 calc R . .
H16B H 0.4309 0.3228 0.0942 0.039 Uiso 1 1 calc R . .
H16C H 0.5625 0.3338 0.0593 0.039 Uiso 1 1 calc R . .
C17 C 0.3886(10) 0.2366(6) -0.1092(9) 0.028(3) Uani 1 1 d DU . .
H17A H 0.4394 0.2619 -0.1530 0.042 Uiso 1 1 calc R . .
H17B H 0.3106 0.2682 -0.1130 0.042 Uiso 1 1 calc R . .
H17C H 0.3533 0.1883 -0.1500 0.042 Uiso 1 1 calc R . .
C18 C 0.4104(11) 0.1767(6) 0.0969(10) 0.032(3) Uani 1 1 d DU . .
H18A H 0.4734 0.1676 0.1850 0.049 Uiso 1 1 calc R . .
H18B H 0.3804 0.1285 0.0533 0.049 Uiso 1 1 calc R . .
H18C H 0.3290 0.2047 0.0944 0.049 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
As As 0.0499 2.0058 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 As1 N1 80.4(3) . 3_655 ?
N1 As1 Cl1 101.8(3) . . ?
N1 As1 Cl1 104.5(3) 3_655 . ?
C1 N1 As1 117.8(6) . . ?
C1 N1 As1 140.2(6) . 3_655 ?
As1 N1 As1 99.6(3) . 3_655 ?
C6 C1 C2 118.7(8) . . ?
C6 C1 N1 117.6(7) . . ?
C2 C1 N1 123.4(7) . . ?
C3 C2 C1 118.4(9) . . ?
C3 C2 C7 118.7(8) . . ?
C1 C2 C7 122.9(8) . . ?
C2 C3 C4 123.6(9) . . ?
C2 C3 H3 111.2 . . ?
C4 C3 H3 124.7 . . ?
C3 C4 C5 115.1(9) . . ?
C3 C4 C8 120.7(8) . . ?
C5 C4 C8 124.2(8) . . ?
C4 C5 C6 124.8(9) . . ?
C4 C5 H5 109.5 . . ?
C6 C5 H5 125.7 . . ?
C5 C6 C1 116.9(8) . . ?
C5 C6 C9 114.1(7) . . ?
C1 C6 C9 128.8(8) . . ?
C12 C7 C11 106.7(9) . . ?
C12 C7 C10 105.5(8) . . ?
C11 C7 C10 111.9(9) . . ?
C12 C7 C2 113.1(8) . . ?
C11 C7 C2 111.7(8) . . ?
C10 C7 C2 107.9(8) . . ?
C14 C8 C15 110.1(9) . . ?
C14 C8 C13 108.9(9) . . ?
C15 C8 C13 108.3(9) . . ?
C14 C8 C4 110.2(8) . . ?
C15 C8 C4 112.2(8) . . ?
C13 C8 C4 107.1(8) . . ?
C17 C9 C16 108.4(8) . . ?
C17 C9 C18 109.5(8) . . ?
C16 C9 C18 104.9(8) . . ?
C17 C9 C6 112.5(7) . . ?
C16 C9 C6 108.1(7) . . ?
C18 C9 C6 113.1(8) . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 C18 H18A 109.5 . . ?
C9 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C9 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
As1 N1 1.840(8) . ?
As1 N1 1.855(7) 3_655 ?
As1 Cl1 2.235(4) . ?
N1 C1 1.469(11) . ?
N1 As1 1.855(7) 3_655 ?
C1 C6 1.402(8) . ?
C1 C2 1.419(8) . ?
C2 C3 1.380(8) . ?
C2 C7 1.557(13) . ?
C3 C4 1.383(8) . ?
C3 H3 0.9400 . ?
C4 C5 1.386(8) . ?
C4 C8 1.539(13) . ?
C5 C6 1.394(8) . ?
C5 H5 0.9400 . ?
C6 C9 1.553(12) . ?
C7 C12 1.538(10) . ?
C7 C11 1.540(11) . ?
C7 C10 1.556(11) . ?
C8 C14 1.521(10) . ?
C8 C15 1.528(11) . ?
C8 C13 1.538(11) . ?
C9 C17 1.530(10) . ?
C9 C16 1.537(10) . ?
C9 C18 1.545(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 As1 N1 C1 166.0(8) 3_655 . . . ?
Cl1 As1 N1 C1 63.0(6) . . . . ?
N1 As1 N1 As1 0.0 3_655 . . 3_655 ?
Cl1 As1 N1 As1 -103.0(3) . . . 3_655 ?
As1 N1 C1 C6 59.5(10) . . . . ?
As1 N1 C1 C6 -142.3(8) 3_655 . . . ?
As1 N1 C1 C2 -113.6(9) . . . . ?
As1 N1 C1 C2 44.5(15) 3_655 . . . ?
C6 C1 C2 C3 -16.2(15) . . . . ?
N1 C1 C2 C3 156.9(10) . . . . ?
C6 C1 C2 C7 161.3(9) . . . . ?
N1 C1 C2 C7 -25.5(15) . . . . ?
C1 C2 C3 C4 4.0(17) . . . . ?
C7 C2 C3 C4 -173.7(9) . . . . ?
C2 C3 C4 C5 6.0(16) . . . . ?
C2 C3 C4 C8 -175.0(10) . . . . ?
C3 C4 C5 C6 -4.2(15) . . . . ?
C8 C4 C5 C6 176.9(9) . . . . ?
C4 C5 C6 C1 -7.6(15) . . . . ?
C4 C5 C6 C9 167.5(9) . . . . ?
C2 C1 C6 C5 17.6(14) . . . . ?
N1 C1 C6 C5 -155.9(9) . . . . ?
C2 C1 C6 C9 -156.6(9) . . . . ?
N1 C1 C6 C9 29.9(14) . . . . ?
C3 C2 C7 C12 9.1(14) . . . . ?
C1 C2 C7 C12 -168.4(10) . . . . ?
C3 C2 C7 C11 -111.2(11) . . . . ?
C1 C2 C7 C11 71.2(12) . . . . ?
C3 C2 C7 C10 125.4(10) . . . . ?
C1 C2 C7 C10 -52.2(12) . . . . ?
C3 C4 C8 C14 -53.1(13) . . . . ?
C5 C4 C8 C14 125.7(11) . . . . ?
C3 C4 C8 C15 -176.1(10) . . . . ?
C5 C4 C8 C15 2.7(15) . . . . ?
C3 C4 C8 C13 65.2(12) . . . . ?
C5 C4 C8 C13 -116.0(11) . . . . ?
C5 C6 C9 C17 77.3(10) . . . . ?
C1 C6 C9 C17 -108.4(11) . . . . ?
C5 C6 C9 C16 -42.3(11) . . . . ?
C1 C6 C9 C16 132.0(10) . . . . ?
C5 C6 C9 C18 -158.0(9) . . . . ?
C1 C6 C9 C18 16.4(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101379755
