#------------------------------------------------------------------------------
#$Date: 2016-03-23 01:52:49 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179159 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/20/4312081.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_4312081
loop_
_publ_author_name
'June-Ho Jung'
'Srinagesh K. Potluri'
'Hongming Zhang'
'Patty Wisian-Neilson'
_publ_contact_author
;
      Patty Wisian-Neilson
      Department of Chemistry
      Southern Methodist University
      Dallas, Texas 75275
      USA
;
_publ_contact_author_email       pwisian@smu.edu
_publ_contact_author_fax         '+1 214 768 4089'
_publ_contact_author_phone       '+1 214 768 2483'
_publ_section_title
;
 Synthesis and Structure of Nongeminally Substituted Cyclic Phosphazenes
 with Haloalkyl and Thioester Functional Groups
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7784
_journal_page_last               7791
_journal_paper_doi               10.1021/ic049063z
_journal_volume                  43
_journal_year                    2004
_chemical_formula_sum            'C21 H22 Br2 N3 P3'
_chemical_formula_weight         569.15
_chemical_name_systematic
; 
 ? 
;
_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                 105.310(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9206(6)
_cell_length_b                   12.6846(9)
_cell_length_c                   17.7519(16)
_cell_measurement_reflns_used    28
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     2371.8(3)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker XSCANS'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_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  0.032
_diffrn_reflns_av_sigmaI/netI    0.069
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5272
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        7.12
_diffrn_standards_interval_count 147
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.633
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_type   '\y scan'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.57
_refine_diff_density_min         -0.43
_refine_diff_density_rms         0.08
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.100
_refine_ls_R_factor_gt           0.050
_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/[σ²(Fo²)+(0.0601P)²+0.7558P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.113
_refine_ls_wR_factor_ref         0.126
_reflns_number_gt                2589
_reflns_number_total             4123
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic049063zsi20040715_125537_6.cif
_cod_data_source_block           7_[jh-br2]
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+0.7558P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+0.7558P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4312081
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.39311(14) 0.01692(11) 0.13180(8) 0.0370(4) Uani 1 d . . .
P2 P 0.36535(14) -0.08677(11) 0.26344(8) 0.0372(4) Uani 1 d . . .
P3 P 0.42538(13) -0.20093(11) 0.14425(8) 0.0361(3) Uani 1 d . . .
N1 N 0.4084(4) -0.0951(3) 0.0940(2) 0.0402(11) Uani 1 d . . .
N2 N 0.3949(4) 0.0188(3) 0.2221(3) 0.0416(11) Uani 1 d . . .
N3 N 0.4040(5) -0.1956(3) 0.2298(2) 0.0443(12) Uani 1 d . . .
Br1 Br 0.68276(6) 0.04872(6) 0.16063(4) 0.0619(2) Uani 1 d . . .
Br3 Br 0.63646(7) -0.28438(6) 0.06814(4) 0.0674(3) Uani 1 d . . .
C1 C 0.5151(5) 0.1057(5) 0.1184(3) 0.0477(15) Uani 1 d . . .
H1A H 0.5080 0.1723 0.1438 0.057 Uiso 1 calc R . .
H1B H 0.5022 0.1193 0.0631 0.057 Uiso 1 calc R . .
C2 C 0.4441(6) -0.0786(5) 0.3655(3) 0.0477(15) Uani 1 d . . .
H2A H 0.5340 -0.0853 0.3729 0.071 Uiso 1 calc R . .
H2B H 0.4146 -0.1344 0.3928 0.071 Uiso 1 calc R . .
H2C H 0.4258 -0.0118 0.3855 0.071 Uiso 1 calc R . .
C3 C 0.5836(5) -0.2529(5) 0.1617(3) 0.0461(14) Uani 1 d . . .
H3A H 0.5891 -0.3169 0.1923 0.055 Uiso 1 calc R . .
H3B H 0.6425 -0.2024 0.1927 0.055 Uiso 1 calc R . .
C11 C 0.2531(5) 0.0806(4) 0.0739(3) 0.0394(13) Uani 1 d . . .
C12 C 0.2108(7) 0.1731(5) 0.0992(4) 0.070(2) Uani 1 d . . .
H12 H 0.2542 0.2013 0.1472 0.085 Uiso 1 calc R . .
C13 C 0.1049(7) 0.2243(6) 0.0544(5) 0.085(2) Uani 1 d . . .
H13 H 0.0774 0.2863 0.0726 0.102 Uiso 1 calc R . .
C14 C 0.0402(7) 0.1850(6) -0.0164(4) 0.069(2) Uani 1 d . . .
H14 H -0.0312 0.2196 -0.0464 0.083 Uiso 1 calc R . .
C15 C 0.0813(6) 0.0949(6) -0.0423(4) 0.0663(19) Uani 1 d . . .
H15 H 0.0379 0.0677 -0.0907 0.080 Uiso 1 calc R . .
C16 C 0.1877(6) 0.0424(5) 0.0023(3) 0.0559(16) Uani 1 d . . .
H16 H 0.2147 -0.0194 -0.0166 0.067 Uiso 1 calc R . .
C21 C 0.1981(5) -0.0923(4) 0.2601(3) 0.0381(13) Uani 1 d . . .
C22 C 0.1353(6) -0.0044(5) 0.2746(4) 0.0569(17) Uani 1 d . . .
H22 H 0.1771 0.0601 0.2827 0.068 Uiso 1 calc R . .
C23 C 0.0093(6) -0.0110(6) 0.2772(4) 0.0676(19) Uani 1 d . . .
H23 H -0.0320 0.0490 0.2880 0.081 Uiso 1 calc R . .
C24 C -0.0535(6) -0.1038(6) 0.2642(4) 0.068(2) Uani 1 d . . .
H24 H -0.1379 -0.1076 0.2656 0.081 Uiso 1 calc R . .
C25 C 0.0073(7) -0.1917(6) 0.2489(4) 0.071(2) Uani 1 d . . .
H25 H -0.0355 -0.2558 0.2403 0.086 Uiso 1 calc R . .
C26 C 0.1313(6) -0.1860(5) 0.2463(4) 0.0566(16) Uani 1 d . . .
H26 H 0.1714 -0.2464 0.2351 0.068 Uiso 1 calc R . .
C31 C 0.3233(5) -0.3005(4) 0.0877(3) 0.0373(12) Uani 1 d . . .
C32 C 0.2729(5) -0.2883(5) 0.0078(3) 0.0487(15) Uani 1 d . . .
H32 H 0.2912 -0.2283 -0.0173 0.058 Uiso 1 calc R . .
C33 C 0.1956(6) -0.3656(6) -0.0338(4) 0.0636(19) Uani 1 d . . .
H33 H 0.1605 -0.3571 -0.0872 0.076 Uiso 1 calc R . .
C34 C 0.1693(6) -0.4559(6) 0.0027(4) 0.0670(19) Uani 1 d . . .
H34 H 0.1180 -0.5086 -0.0255 0.080 Uiso 1 calc R . .
C35 C 0.2209(7) -0.4656(6) 0.0814(4) 0.072(2) Uani 1 d . . .
H35 H 0.2034 -0.5257 0.1068 0.086 Uiso 1 calc R . .
C36 C 0.2979(6) -0.3888(5) 0.1241(4) 0.0575(17) Uani 1 d . . .
H36 H 0.3324 -0.3973 0.1776 0.069 Uiso 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'
Br Br -0.2901 2.4595 '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
N2 P1 N1 117.4(2) . . y
N2 P1 C11 110.6(2) . . y
N1 P1 C11 109.1(2) . . y
N2 P1 C1 107.9(3) . . y
N1 P1 C1 109.6(3) . . y
C11 P1 C1 101.0(2) . . y
N2 P2 N3 116.4(2) . . y
N2 P2 C2 108.3(3) . . y
N3 P2 C2 108.8(3) . . y
N2 P2 C21 109.9(3) . . y
N3 P2 C21 108.5(3) . . y
C2 P2 C21 104.2(3) . . y
N1 P3 N3 118.1(2) . . y
N1 P3 C3 111.7(3) . . y
N3 P3 C3 103.1(2) . . y
N1 P3 C31 108.3(2) . . y
N3 P3 C31 109.6(2) . . y
C3 P3 C31 105.3(3) . . y
P3 N1 P1 121.5(3) . . y
P1 N2 P2 119.8(3) . . y
P3 N3 P2 120.6(3) . . y
P1 C1 Br1 111.9(3) . . y
P3 C3 Br3 114.7(3) . . y
C16 C11 C12 117.7(5) . . ?
C16 C11 P1 121.9(4) . . ?
C12 C11 P1 120.3(5) . . ?
C11 C12 C13 120.9(7) . . ?
C14 C13 C12 120.7(7) . . ?
C15 C14 C13 119.1(6) . . ?
C14 C15 C16 120.8(7) . . ?
C11 C16 C15 120.8(6) . . ?
C22 C21 C26 117.8(6) . . ?
C22 C21 P2 120.9(5) . . ?
C26 C21 P2 121.3(4) . . ?
C21 C22 C23 120.5(6) . . ?
C24 C23 C22 120.5(7) . . ?
C23 C24 C25 119.7(6) . . ?
C24 C25 C26 120.2(6) . . ?
C25 C26 C21 121.3(6) . . ?
C36 C31 C32 120.2(5) . . ?
C36 C31 P3 119.1(4) . . ?
C32 C31 P3 120.7(4) . . ?
C33 C32 C31 119.4(6) . . ?
C32 C33 C34 120.8(6) . . ?
C35 C34 C33 118.3(6) . . ?
C34 C35 C36 121.7(7) . . ?
C31 C36 C35 119.6(6) . . ?
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 N2 1.599(4) . y
P1 N1 1.599(4) . y
P1 C11 1.794(5) . y
P1 C1 1.808(5) . y
P2 N2 1.600(4) . y
P2 N3 1.604(4) . y
P2 C2 1.792(5) . y
P2 C21 1.813(6) . y
P3 N1 1.596(4) . y
P3 N3 1.598(4) . y
P3 C3 1.798(5) . y
P3 C31 1.804(5) . y
Br1 C1 1.927(5) . y
Br3 C3 1.939(5) . y
C11 C16 1.371(8) . ?
C11 C12 1.379(8) . ?
C12 C13 1.381(9) . ?
C13 C14 1.362(9) . ?
C14 C15 1.352(9) . ?
C15 C16 1.391(9) . ?
C21 C22 1.368(8) . ?
C21 C26 1.382(8) . ?
C22 C23 1.391(9) . ?
C23 C24 1.352(9) . ?
C24 C25 1.360(9) . ?
C25 C26 1.369(9) . ?
C31 C36 1.358(7) . ?
C31 C32 1.388(7) . ?
C32 C33 1.376(8) . ?
C33 C34 1.383(10) . ?
C34 C35 1.367(9) . ?
C35 C36 1.377(8) . ?
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
C11 P1 C1 Br1 -171.0(3) . . . . ?
N1 P1 C1 Br1 -56.0(4) . . . . ?
C31 P3 C3 Br3 59.0(4) . . . . ?
N3 P3 C3 Br3 173.9(3) . . . . ?
