#------------------------------------------------------------------------------
#$Date: 2017-07-25 12:37:42 +0300 (Tue, 25 Jul 2017) $
#$Revision: 199153 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/21/2242183.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_2242183
loop_
_publ_author_name
'Issaoui, Chokri'
'Chebbi, Hammouda'
'Alouani, Khaled'
'Guesmi, Abderrahmen'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of the new
 cyclodiphosphazane [EtNP(S)NMe₂]₂
;
_journal_coeditor_code           PK2598
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              682
_journal_page_last               686
_journal_paper_doi               10.1107/S2056989017005187
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C8 H22 N4 P2 S2'
_chemical_formula_moiety         'C8 H22 N4 P2 S2'
_chemical_formula_sum            'C8 H22 N4 P2 S2'
_chemical_formula_weight         300.35
_chemical_name_common
;
2,4-Bis(dimethylamino)-1,3-diethylcyclodiphosphazane-2,4-dithione
;
_chemical_name_systematic
2,4-Bis(dimethylamino)-1,3-diethyl-1,3,2λ⁵,4λ⁵-diazadiphosphetidine-2,4-dithione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.39(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1975(10)
_cell_length_b                   11.448(2)
_cell_length_c                   9.645(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     789.8(2)
_computing_cell_refinement
;
CAD-4 EXPRESS (Duisenberg, 1992; Macíček & Yordanov, 1992)
;
_computing_data_collection
;
CAD-4 EXPRESS (Duisenberg, 1992; Macíček & Yordanov, 1992)
;
_computing_data_reduction
;
XCAD4 (Harms & Wocadlo, 1995)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2006)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3150
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.971
_diffrn_reflns_theta_min         2.772
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.524
_exptl_absorpt_correction_T_max  0.9997
_exptl_absorpt_correction_T_min  0.9994
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
(North et al.,1968)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         1724
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0405
_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)+(0.0779P)²+0.1315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1267
_reflns_number_gt                1463
_reflns_number_total             1724
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            pk2598sup1.cif
_cod_data_source_block           I
_cod_database_code               2242183
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/7
loop_
_space_group_symop_operation_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_occupancy
P P1 0.50835(7) 0.50319(4) 0.13083(5) 0.0515(2) Uani d 1
S S1 0.33563(10) 0.44283(7) 0.25236(6) 0.0790(3) Uani d 1
N N1 0.4319(2) 0.58738(14) -0.00532(16) 0.0535(4) Uani d 1
N N2 0.6900(3) 0.56638(18) 0.21583(18) 0.0670(5) Uani d 1
C C1 0.7415(5) 0.5568(3) 0.3657(3) 0.0952(9) Uani d 1
H H1A 0.8411 0.5013 0.3838 0.143 Uiso calc 1
H H1B 0.6352 0.5313 0.4096 0.143 Uiso calc 1
H H1C 0.7821 0.6316 0.4024 0.143 Uiso calc 1
C C2 0.8350(4) 0.6172(3) 0.1411(3) 0.0814(7) Uani d 1
H H2A 0.8611 0.6952 0.1740 0.122 Uiso calc 1
H H2B 0.7932 0.6190 0.0431 0.122 Uiso calc 1
H H2C 0.9465 0.5708 0.1569 0.122 Uiso calc 1
C C3 0.3911(4) 0.7123(2) -0.0151(3) 0.0779(7) Uani d 1
H H3A 0.4058 0.7454 0.0781 0.093 Uiso calc 1
H H3B 0.4816 0.7496 -0.0679 0.093 Uiso calc 1
C C4 0.2046(5) 0.7387(3) -0.0806(5) 0.1204(13) Uani d 1
H H4A 0.1842 0.7000 -0.1692 0.181 Uiso calc 1
H H4B 0.1921 0.8216 -0.0940 0.181 Uiso calc 1
H H4C 0.1139 0.7121 -0.0218 0.181 Uiso calc 1
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
-4 -3 -2
-4 -2 -3
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N2 P1 N1 . . 108.31(10)
N2 P1 N1 . 3_665 112.28(10)
N1 P1 N1 . 3_665 83.02(8)
N2 P1 S1 . . 112.81(8)
N1 P1 S1 . . 120.38(7)
N1 P1 S1 3_665 . 116.69(7)
N2 P1 P1 . 3_665 117.58(8)
S1 P1 P1 . 3_665 129.60(4)
C3 N1 P1 . . 131.38(16)
C3 N1 P1 . 3_665 128.43(17)
P1 N1 P1 . 3_665 96.98(8)
C2 N2 C1 . . 113.9(2)
C2 N2 P1 . . 120.47(15)
C1 N2 P1 . . 124.5(2)
N2 C1 H1A . . 109.5
N2 C1 H1B . . 109.5
H1A C1 H1B . . 109.5
N2 C1 H1C . . 109.5
H1A C1 H1C . . 109.5
H1B C1 H1C . . 109.5
N2 C2 H2A . . 109.5
N2 C2 H2B . . 109.5
H2A C2 H2B . . 109.5
N2 C2 H2C . . 109.5
H2A C2 H2C . . 109.5
H2B C2 H2C . . 109.5
C4 C3 N1 . . 113.7(2)
C4 C3 H3A . . 108.8
N1 C3 H3A . . 108.8
C4 C3 H3B . . 108.8
N1 C3 H3B . . 108.8
H3A C3 H3B . . 107.7
C3 C4 H4A . . 109.5
C3 C4 H4B . . 109.5
H4A C4 H4B . . 109.5
C3 C4 H4C . . 109.5
H4A C4 H4C . . 109.5
H4B C4 H4C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
P1 N2 . 1.6325(19)
P1 N1 . 1.6719(16)
P1 N1 3_665 1.6856(17)
P1 S1 . 1.9291(9)
P1 P1 3_665 2.5143(10)
N1 C3 . 1.460(3)
N1 P1 3_665 1.6857(17)
N2 C2 . 1.455(3)
N2 C1 . 1.456(3)
C1 H1A . 0.9600
C1 H1B . 0.9600
C1 H1C . 0.9600
C2 H2A . 0.9600
C2 H2B . 0.9600
C2 H2C . 0.9600
C3 C4 . 1.450(4)
C3 H3A . 0.9700
C3 H3B . 0.9700
C4 H4A . 0.9600
C4 H4B . 0.9600
C4 H4C . 0.9600

_cod_database_fobs_code 2242183
