#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/36/2213669.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2213669
loop_
_publ_author_name
'Alouani, Khaled'
'Guesmi, Abderrahmen'
'Driss, Ahmed'
_publ_section_title
;Le ligand neutre
 bis(N,N,N',N'-tétraméthylsélénophosphoramidoyl)méthylamine
;
_journal_coeditor_code           BH2099
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2972
_journal_page_last               o2972
_journal_paper_doi               10.1107/S1600536807022970
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C9 H27 N5 P2 Se2'
_chemical_formula_moiety         'C9 H27 N5 P2 Se2'
_chemical_formula_sum            'C9 H27 N5 P2 Se2'
_chemical_formula_weight         425.22
_chemical_name_common            C9H27N5P2Se2
_chemical_name_systematic
;
bis(N,N,N',N'-tetramethylselenophosphoramidoyl)methylamine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.68(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.525(4)
_cell_length_b                   11.202(6)
_cell_length_c                   12.908(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.91
_cell_measurement_theta_min      11.40
_cell_volume                     1658.3(13)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Duisenberg, 1992)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1998)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0785
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3163
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         2.41
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    4.645
_exptl_absorpt_correction_T_max  0.498
_exptl_absorpt_correction_T_min  0.381
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.195
_refine_diff_density_min         -0.754
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3007
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.1415
_refine_ls_R_factor_gt           0.0665
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1128P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.1930
_reflns_number_gt                1584
_reflns_number_total             3007
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2099.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2213669
_cod_database_fobs_code          2213669
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
P P1 0.34331(18) 0.48657(17) 0.19364(15) 0.0375(5) Uani d . 1
P P2 0.13366(19) 0.46216(17) 0.31991(15) 0.0381(5) Uani d . 1
Se Se1 0.31423(10) 0.65203(8) 0.15216(9) 0.0694(4) Uani d . 1
Se Se2 0.12448(11) 0.34297(9) 0.43767(8) 0.0694(4) Uani d . 1
N N1 0.2247(5) 0.4206(5) 0.2309(4) 0.0356(15) Uani d . 1
N N2 0.4459(5) 0.4667(6) 0.2909(5) 0.0448(16) Uani d . 1
N N3 0.3857(6) 0.4187(6) 0.0935(5) 0.0490(18) Uani d . 1
N N4 0.0090(6) 0.4783(7) 0.2482(5) 0.0516(18) Uani d . 1
N N5 0.1756(6) 0.5829(6) 0.3662(5) 0.0443(16) Uani d . 1
C C1 0.2007(9) 0.3098(8) 0.1906(8) 0.065(3) Uani d . 1
H H1 0.1930 0.3140 0.1160 0.080 Uiso calc R 1
H H2 0.1292 0.2812 0.2139 0.080 Uiso calc R 1
H H3 0.2630 0.2563 0.2136 0.080 Uiso calc R 1
C C2 0.4459(9) 0.3796(9) 0.3679(7) 0.065(3) Uani d . 1
H H4 0.5001 0.3177 0.3548 0.080 Uiso calc R 1
H H5 0.3691 0.3463 0.3674 0.080 Uiso calc R 1
H H6 0.4684 0.4149 0.4347 0.080 Uiso calc R 1
C C3 0.2662(9) 0.5941(9) 0.4530(7) 0.071(3) Uani d . 1
H H7 0.3285 0.6427 0.4323 0.080 Uiso calc R 1
H H8 0.2957 0.5164 0.4727 0.080 Uiso calc R 1
H H9 0.2340 0.6307 0.5110 0.080 Uiso calc R 1
C C4 -0.1022(8) 0.4755(10) 0.2966(9) 0.076(3) Uani d . 1
H H10 -0.1348 0.5543 0.2962 0.080 Uiso calc R 1
H H11 -0.0879 0.4477 0.3671 0.080 Uiso calc R 1
H H12 -0.1558 0.4226 0.2579 0.080 Uiso calc R 1
C C5 0.5581(9) 0.5224(11) 0.2896(9) 0.081(3) Uani d . 1
H H13 0.5840 0.5511 0.3581 0.080 Uiso calc R 1
H H14 0.5521 0.5881 0.2416 0.080 Uiso calc R 1
H H15 0.6130 0.4652 0.2683 0.080 Uiso calc R 1
C C6 0.4616(10) 0.3235(8) 0.1027(9) 0.076(3) Uani d . 1
H H16 0.4182 0.2503 0.0979 0.080 Uiso calc R 1
H H17 0.5077 0.3273 0.1687 0.080 Uiso calc R 1
H H18 0.5119 0.3266 0.0477 0.080 Uiso calc R 1
C C7 0.1145(9) 0.6847(8) 0.3385(8) 0.068(3) Uani d . 1
H H19 0.0667 0.7059 0.3924 0.080 Uiso calc R 1
H H20 0.0660 0.6712 0.2747 0.080 Uiso calc R 1
H H21 0.1681 0.7485 0.3288 0.080 Uiso calc R 1
C C8 -0.0029(9) 0.5091(11) 0.1383(8) 0.080(3) Uani d . 1
H H22 -0.0530 0.4523 0.1004 0.080 Uiso calc R 1
H H23 0.0724 0.5079 0.1126 0.080 Uiso calc R 1
H H24 -0.0360 0.5875 0.1293 0.080 Uiso calc R 1
C C9 0.3327(11) 0.4376(10) -0.0141(7) 0.081(4) Uani d . 1
H H25 0.3929 0.4409 -0.0604 0.080 Uiso calc R 1
H H26 0.2901 0.5114 -0.0179 0.080 Uiso calc R 1
H H27 0.2806 0.3729 -0.0341 0.080 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
P P 0.1023 0.0942 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 7 5
1 6 4
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N3 P1 N2 107.1(4)
N3 P1 N1 110.1(3)
N2 P1 N1 105.5(3)
N3 P1 Se1 106.6(3)
N2 P1 Se1 115.3(3)
N1 P1 Se1 112.2(2)
N5 P2 N4 110.2(4)
N5 P2 N1 108.2(3)
N4 P2 N1 102.4(3)
N5 P2 Se2 109.0(3)
N4 P2 Se2 112.7(3)
N1 P2 Se2 114.1(2)
C1 N1 P1 115.8(5)
C1 N1 P2 113.1(5)
P1 N1 P2 130.9(4)
C2 N2 C5 112.1(7)
C2 N2 P1 125.8(6)
C5 N2 P1 120.7(6)
C6 N3 C9 113.1(8)
C6 N3 P1 122.4(6)
C9 N3 P1 123.7(7)
C8 N4 C4 114.6(8)
C8 N4 P2 124.7(6)
C4 N4 P2 120.4(7)
C7 N5 C3 116.1(7)
C7 N5 P2 119.9(6)
C3 N5 P2 123.2(6)
N1 C1 H1 109.5
N1 C1 H2 109.5
H1 C1 H2 109.5
N1 C1 H3 109.5
H1 C1 H3 109.5
H2 C1 H3 109.5
N2 C2 H4 109.5
N2 C2 H5 109.5
H4 C2 H5 109.5
N2 C2 H6 109.5
H4 C2 H6 109.5
H5 C2 H6 109.5
N5 C3 H7 109.5
N5 C3 H8 109.5
H7 C3 H8 109.5
N5 C3 H9 109.5
H7 C3 H9 109.5
H8 C3 H9 109.5
N4 C4 H10 109.5
N4 C4 H11 109.5
H10 C4 H11 109.5
N4 C4 H12 109.5
H10 C4 H12 109.5
H11 C4 H12 109.5
N2 C5 H13 109.5
N2 C5 H14 109.5
H13 C5 H14 109.5
N2 C5 H15 109.5
H13 C5 H15 109.5
H14 C5 H15 109.5
N3 C6 H16 109.5
N3 C6 H17 109.5
H16 C6 H17 109.5
N3 C6 H18 109.5
H16 C6 H18 109.5
H17 C6 H18 109.5
N5 C7 H19 109.5
N5 C7 H20 109.5
H19 C7 H20 109.5
N5 C7 H21 109.5
H19 C7 H21 109.5
H20 C7 H21 109.5
N4 C8 H22 109.5
N4 C8 H23 109.5
H22 C8 H23 109.5
N4 C8 H24 109.5
H22 C8 H24 109.5
H23 C8 H24 109.5
N3 C9 H25 109.5
N3 C9 H26 109.5
H25 C9 H26 109.5
N3 C9 H27 109.5
H25 C9 H27 109.5
H26 C9 H27 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 N3 1.617(7)
P1 N2 1.652(7)
P1 N1 1.665(6)
P1 Se1 1.949(2)
P2 N5 1.537(7)
P2 N4 1.641(7)
P2 N1 1.696(6)
P2 Se2 2.034(2)
N1 C1 1.364(10)
N2 C2 1.394(10)
N2 C5 1.436(11)
N3 C6 1.377(12)
N3 C9 1.476(11)
N4 C8 1.453(11)
N4 C4 1.480(12)
N5 C7 1.369(10)
N5 C3 1.459(11)
C1 H1 0.9600
C1 H2 0.9600
C1 H3 0.9600
C2 H4 0.9600
C2 H5 0.9600
C2 H6 0.9600
C3 H7 0.9600
C3 H8 0.9600
C3 H9 0.9600
C4 H10 0.9600
C4 H11 0.9600
C4 H12 0.9600
C5 H13 0.9600
C5 H14 0.9600
C5 H15 0.9600
C6 H16 0.9600
C6 H17 0.9600
C6 H18 0.9600
C7 H19 0.9600
C7 H20 0.9600
C7 H21 0.9600
C8 H22 0.9600
C8 H23 0.9600
C8 H24 0.9600
C9 H25 0.9600
C9 H26 0.9600
C9 H27 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1 H1 Se2 4_565 0.96 2.94 3.714(9) 138.4
C2 H4 Se1 2_645 0.96 2.84 3.788(10) 169.5
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655241
