#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/35/7003564.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_7003564
loop_
_publ_author_name
'Burck, Sebastian'
'Gudat, Dietrich'
'Nieger, Martin'
'Schalley, Christoph A.'
'Weilandt, Torsten'
_publ_section_title
;
 Phosphazene vs.diazaphospholene PN-bond cleavage in spirocyclic
 cyclodiphosphazenes
;
_journal_issue                   26
_journal_name_full               'Dalton Transactions'
_journal_page_first              3478
_journal_page_last               3485
_journal_paper_doi               10.1039/b717219b
_journal_year                    2008
_chemical_formula_moiety         'C18 H20 N5 P'
_chemical_formula_sum            'C18 H20 N5 P'
_chemical_formula_weight         337.36
_chemical_name_common
2-Azido-1,3-bis(2,6-dimethylphenyl)-1,3,2-diazaphospholene
_chemical_name_systematic
;
2-Azido-1,3-bis(2,6-dimethylphenyl)-1,3,2-diazaphospholene
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.415(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7383(8)
_cell_length_b                   10.8003(8)
_cell_length_c                   12.8025(6)
_cell_measurement_reflns_used    5135
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1761.29(19)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       Collect
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 2 deg.'
_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  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16649
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4028
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0516P)²+0.6189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                3189
_reflns_number_total             4028
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b717219b.txt
_cod_data_source_block           gudat130_compound_2a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7003564
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_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
P1 P 0.77400(3) 0.70689(4) 0.42106(3) 0.02488(12) Uani 1 1 d . . .
N11 N 0.68400(11) 0.63259(14) 0.32447(10) 0.0318(3) Uani 1 1 d . . .
N12 N 0.72986(11) 0.56467(14) 0.26285(10) 0.0348(3) Uani 1 1 d . . .
N13 N 0.76927(15) 0.50010(18) 0.20517(14) 0.0555(5) Uani 1 1 d . . .
N2 N 0.69586(10) 0.82408(12) 0.45863(9) 0.0249(3) Uani 1 1 d . . .
C3 C 0.63384(12) 0.79355(15) 0.54618(12) 0.0285(3) Uani 1 1 d . . .
H3 H 0.5787 0.8439 0.5722 0.034 Uiso 1 1 calc R . .
C4 C 0.66224(12) 0.68567(15) 0.58753(12) 0.0291(3) Uani 1 1 d . . .
H4 H 0.6299 0.6492 0.6467 0.035 Uiso 1 1 calc R . .
N5 N 0.74632(9) 0.63211(12) 0.53272(9) 0.0251(3) Uani 1 1 d . . .
C6 C 0.68528(11) 0.93756(14) 0.40129(10) 0.0234(3) Uani 1 1 d . . .
C7 C 0.77128(11) 1.01774(15) 0.39518(11) 0.0258(3) Uani 1 1 d . . .
C8 C 0.75999(12) 1.12708(15) 0.33893(12) 0.0293(3) Uani 1 1 d . . .
H8 H 0.8177 1.1824 0.3339 0.035 Uiso 1 1 calc R . .
C9 C 0.66605(12) 1.15662(16) 0.29024(12) 0.0307(3) Uani 1 1 d . . .
H9 H 0.6595 1.2318 0.2522 0.037 Uiso 1 1 calc R . .
C10 C 0.58153(12) 1.07667(16) 0.29697(11) 0.0292(3) Uani 1 1 d . . .
H10 H 0.5172 1.0976 0.2633 0.035 Uiso 1 1 calc R . .
C11 C 0.58935(11) 0.96601(15) 0.35231(11) 0.0257(3) Uani 1 1 d . . .
C12 C 0.49632(13) 0.87969(17) 0.35626(15) 0.0369(4) Uani 1 1 d . . .
H12A H 0.4583 0.8927 0.4216 0.055 Uiso 1 1 calc R . .
H12B H 0.5208 0.7938 0.3529 0.055 Uiso 1 1 calc R . .
H12C H 0.4495 0.8965 0.2969 0.055 Uiso 1 1 calc R . .
C13 C 0.87496(12) 0.98976(17) 0.44727(13) 0.0333(4) Uani 1 1 d . . .
H13A H 0.8627 0.9565 0.5174 0.050 Uiso 1 1 calc R . .
H13B H 0.9165 1.0659 0.4526 0.050 Uiso 1 1 calc R . .
H13C H 0.9132 0.9286 0.4057 0.050 Uiso 1 1 calc R . .
C14 C 0.79806(12) 0.51928(15) 0.56349(11) 0.0274(3) Uani 1 1 d . . .
C15 C 0.89702(13) 0.52856(18) 0.61192(12) 0.0339(4) Uani 1 1 d . . .
C16 C 0.94772(15) 0.4178(2) 0.63766(13) 0.0449(5) Uani 1 1 d . . .
H16 H 1.0148 0.4207 0.6704 0.054 Uiso 1 1 calc R . .
C17 C 0.90275(17) 0.30509(19) 0.61672(14) 0.0477(5) Uani 1 1 d . . .
H17 H 0.9398 0.2312 0.6333 0.057 Uiso 1 1 calc R . .
C18 C 0.80399(16) 0.29797(18) 0.57165(13) 0.0421(4) Uani 1 1 d . . .
H18 H 0.7730 0.2193 0.5592 0.051 Uiso 1 1 calc R . .
C19 C 0.74940(13) 0.40541(16) 0.54424(12) 0.0317(4) Uani 1 1 d . . .
C20 C 0.64034(14) 0.39676(17) 0.49983(14) 0.0393(4) Uani 1 1 d . . .
H20A H 0.6271 0.3119 0.4760 0.059 Uiso 1 1 calc R . .
H20B H 0.6333 0.4539 0.4407 0.059 Uiso 1 1 calc R . .
H20C H 0.5895 0.4188 0.5538 0.059 Uiso 1 1 calc R . .
C21 C 0.94554(15) 0.6517(2) 0.63589(14) 0.0454(5) Uani 1 1 d . . .
H21A H 1.0088 0.6397 0.6787 0.068 Uiso 1 1 calc R . .
H21B H 0.8953 0.7029 0.6742 0.068 Uiso 1 1 calc R . .
H21C H 0.9643 0.6931 0.5705 0.068 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'
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'
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
N5 P1 N2 89.44(6) . . ?
N5 P1 N11 103.04(6) . . ?
N2 P1 N11 98.71(6) . . ?
N12 N11 P1 112.99(11) . . ?
N13 N12 N11 177.80(19) . . ?
C3 N2 C6 123.61(12) . . ?
C3 N2 P1 112.71(10) . . ?
C6 N2 P1 123.37(9) . . ?
C4 C3 N2 111.59(13) . . ?
C4 C3 H3 124.2 . . ?
N2 C3 H3 124.2 . . ?
C3 C4 N5 111.55(13) . . ?
C3 C4 H4 124.2 . . ?
N5 C4 H4 124.2 . . ?
C4 N5 C14 124.03(12) . . ?
C4 N5 P1 113.02(10) . . ?
C14 N5 P1 122.76(10) . . ?
C7 C6 C11 121.27(14) . . ?
C7 C6 N2 119.13(13) . . ?
C11 C6 N2 119.60(13) . . ?
C8 C7 C6 118.47(14) . . ?
C8 C7 C13 119.14(14) . . ?
C6 C7 C13 122.39(14) . . ?
C9 C8 C7 121.04(15) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 119.96(15) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 120.97(14) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C6 118.29(14) . . ?
C10 C11 C12 119.61(14) . . ?
C6 C11 C12 122.09(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 122.41(15) . . ?
C19 C14 N5 119.67(14) . . ?
C15 C14 N5 117.93(15) . . ?
C16 C15 C14 117.05(17) . . ?
C16 C15 C21 121.50(16) . . ?
C14 C15 C21 121.45(16) . . ?
C17 C16 C15 121.47(17) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 120.57(17) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 120.59(19) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 117.85(16) . . ?
C18 C19 C20 120.11(17) . . ?
C14 C19 C20 121.99(15) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C21 H21A 109.5 . . ?
C15 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C15 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
P1 N5 1.6815(12) . ?
P1 N2 1.6826(13) . ?
P1 N11 1.8620(14) . ?
N11 N12 1.2282(19) . ?
N12 N13 1.135(2) . ?
N2 C3 1.4150(19) . ?
N2 C6 1.4345(19) . ?
C3 C4 1.329(2) . ?
C3 H3 0.9500 . ?
C4 N5 1.4089(19) . ?
C4 H4 0.9500 . ?
N5 C14 1.439(2) . ?
C6 C7 1.399(2) . ?
C6 C11 1.403(2) . ?
C7 C8 1.390(2) . ?
C7 C13 1.506(2) . ?
C8 C9 1.383(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.509(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.398(2) . ?
C14 C15 1.404(2) . ?
C15 C16 1.398(3) . ?
C15 C21 1.497(3) . ?
C16 C17 1.371(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.396(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.500(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
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
N5 P1 N11 N12 -107.84(12) . . . . ?
N2 P1 N11 N12 160.71(12) . . . . ?
P1 N11 N12 N13 161(5) . . . . ?
N5 P1 N2 C3 -11.69(11) . . . . ?
N11 P1 N2 C3 91.42(11) . . . . ?
N5 P1 N2 C6 174.55(12) . . . . ?
N11 P1 N2 C6 -82.35(12) . . . . ?
C6 N2 C3 C4 -177.43(14) . . . . ?
P1 N2 C3 C4 8.83(17) . . . . ?
N2 C3 C4 N5 0.14(19) . . . . ?
C3 C4 N5 C14 175.87(14) . . . . ?
C3 C4 N5 P1 -9.08(17) . . . . ?
N2 P1 N5 C4 11.82(11) . . . . ?
N11 P1 N5 C4 -86.99(11) . . . . ?
N2 P1 N5 C14 -173.06(12) . . . . ?
N11 P1 N5 C14 88.13(13) . . . . ?
C3 N2 C6 C7 119.75(16) . . . . ?
P1 N2 C6 C7 -67.16(17) . . . . ?
C3 N2 C6 C11 -60.38(19) . . . . ?
P1 N2 C6 C11 112.71(13) . . . . ?
C11 C6 C7 C8 -0.2(2) . . . . ?
N2 C6 C7 C8 179.70(13) . . . . ?
C11 C6 C7 C13 179.78(14) . . . . ?
N2 C6 C7 C13 -0.4(2) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C13 C7 C8 C9 -179.75(14) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C9 C10 C11 C6 0.0(2) . . . . ?
C9 C10 C11 C12 -178.76(14) . . . . ?
C7 C6 C11 C10 0.0(2) . . . . ?
N2 C6 C11 C10 -179.82(13) . . . . ?
C7 C6 C11 C12 178.82(14) . . . . ?
N2 C6 C11 C12 -1.0(2) . . . . ?
C4 N5 C14 C19 76.70(19) . . . . ?
P1 N5 C14 C19 -97.88(15) . . . . ?
C4 N5 C14 C15 -103.57(17) . . . . ?
P1 N5 C14 C15 81.84(16) . . . . ?
C19 C14 C15 C16 2.1(2) . . . . ?
N5 C14 C15 C16 -177.66(13) . . . . ?
C19 C14 C15 C21 -177.33(15) . . . . ?
N5 C14 C15 C21 2.9(2) . . . . ?
C14 C15 C16 C17 -0.1(2) . . . . ?
C21 C15 C16 C17 179.28(16) . . . . ?
C15 C16 C17 C18 -1.7(3) . . . . ?
C16 C17 C18 C19 1.6(3) . . . . ?
C17 C18 C19 C14 0.3(2) . . . . ?
C17 C18 C19 C20 -177.25(15) . . . . ?
C15 C14 C19 C18 -2.1(2) . . . . ?
N5 C14 C19 C18 177.58(13) . . . . ?
C15 C14 C19 C20 175.32(14) . . . . ?
N5 C14 C19 C20 -5.0(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 29330081
