#------------------------------------------------------------------------------
#$Date: 2016-03-23 01:52:49 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179159 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/20/4312080.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_4312080
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 H23 Br N3 P3'
_chemical_formula_weight         490.24
_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                 92.183(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.867(1)
_cell_length_b                   12.671(1)
_cell_length_c                   20.352(2)
_cell_measurement_reflns_used    41
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.0
_cell_measurement_theta_min      9.86
_cell_volume                     2285.0(4)
_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 0.936
_diffrn_measured_fraction_theta_max 0.936
_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  0.049
_diffrn_reflns_av_sigmaI/netI    0.111
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5228
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        7.21
_diffrn_standards_interval_count 147
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.021
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.21
_refine_diff_density_min         -0.55
_refine_diff_density_rms         0.09
_refine_ls_extinction_coef       0.0012(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.96
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.96
_refine_ls_R_factor_all          0.164
_refine_ls_R_factor_gt           0.074
_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)+(0.1171P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.186
_refine_ls_wR_factor_ref         0.216
_reflns_number_gt                1972
_reflns_number_total             3954
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic049063zsi20040715_125537_5.cif
_cod_data_source_block           6_[jh-br1]
_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^)+(0.1171P)^2^+0.0000P] 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^)+(0.1171P)^2^+0.0000P] 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               4312080
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
Br1 Br 0.38243(13) 0.88894(9) 0.34381(5) 0.0874(5) Uani 1 d . . .
P1 P 0.3236(2) 1.10098(16) 0.41457(9) 0.0431(5) Uani 1 d . . .
P2 P 0.3435(2) 1.21864(17) 0.29980(9) 0.0487(6) Uani 1 d . . .
P3 P 0.5907(2) 1.20661(16) 0.38886(9) 0.0460(6) Uani 1 d . . .
N1 N 0.4989(6) 1.1233(5) 0.4308(3) 0.0483(16) Uani 1 d . . .
N2 N 0.2514(6) 1.1452(5) 0.3473(3) 0.0536(17) Uani 1 d . . .
N3 N 0.5153(7) 1.2444(6) 0.3208(3) 0.0587(19) Uani 1 d . . .
C1 C 0.2958(9) 0.9582(6) 0.4177(4) 0.053(2) Uani 1 d . . .
H1A H 0.1886 0.9429 0.4179 0.064 Uiso 1 calc R . .
H1B H 0.3420 0.9307 0.4582 0.064 Uiso 1 calc R . .
C2 C 0.3432(10) 1.1567(8) 0.2201(4) 0.076(3) Uani 1 d . . .
H2A H 0.2413 1.1508 0.2028 0.113 Uiso 1 calc R . .
H2B H 0.3872 1.0877 0.2241 0.113 Uiso 1 calc R . .
H2C H 0.4009 1.1987 0.1909 0.113 Uiso 1 calc R . .
C3 C 0.7722(9) 1.1496(7) 0.3735(4) 0.070(3) Uani 1 d . . .
H3A H 0.8353 1.2019 0.3543 0.105 Uiso 1 calc R . .
H3B H 0.7594 1.0911 0.3439 0.105 Uiso 1 calc R . .
H3C H 0.8185 1.1256 0.4142 0.105 Uiso 1 calc R . .
C11 C 0.2135(8) 1.1448(6) 0.4824(3) 0.0430(18) Uani 1 d . . .
C12 C 0.2456(9) 1.1078(7) 0.5451(4) 0.056(2) Uani 1 d . . .
H12 H 0.3228 1.0590 0.5525 0.067 Uiso 1 calc R . .
C13 C 0.1629(10) 1.1434(8) 0.5970(4) 0.068(2) Uani 1 d . . .
H13 H 0.1831 1.1174 0.6391 0.082 Uiso 1 calc R . .
C14 C 0.0516(10) 1.2167(8) 0.5864(4) 0.068(3) Uani 1 d . . .
H14 H -0.0042 1.2398 0.6214 0.081 Uiso 1 calc R . .
C15 C 0.0213(9) 1.2565(7) 0.5245(5) 0.067(2) Uani 1 d . . .
H15 H -0.0535 1.3071 0.5175 0.081 Uiso 1 calc R . .
C16 C 0.1026(9) 1.2207(7) 0.4736(4) 0.057(2) Uani 1 d . . .
H16 H 0.0830 1.2481 0.4318 0.068 Uiso 1 calc R . .
C21 C 0.2408(9) 1.3388(7) 0.2904(3) 0.053(2) Uani 1 d . . .
C22 C 0.3133(12) 1.4376(8) 0.2938(4) 0.077(3) Uani 1 d . . .
H22 H 0.4173 1.4403 0.3017 0.093 Uiso 1 calc R . .
C23 C 0.2342(16) 1.5297(9) 0.2858(5) 0.101(4) Uani 1 d . . .
H23 H 0.2835 1.5945 0.2886 0.121 Uiso 1 calc R . .
C24 C 0.0784(17) 1.5250(11) 0.2732(5) 0.109(4) Uani 1 d . . .
H24 H 0.0230 1.5869 0.2674 0.131 Uiso 1 calc R . .
C25 C 0.0071(12) 1.4291(12) 0.2695(5) 0.098(4) Uani 1 d . . .
H25 H -0.0967 1.4261 0.2612 0.117 Uiso 1 calc R . .
C26 C 0.0871(5) 1.3381(4) 0.2777(2) 0.066(2) Uani 1 d . . .
H26 H 0.0367 1.2738 0.2747 0.080 Uiso 1 calc R . .
C31 C 0.6362(5) 1.3198(4) 0.4400(2) 0.053(2) Uani 1 d R . .
C32 C 0.7140(5) 1.4050(4) 0.4152(2) 0.083(3) Uani 1 d R . .
H32 H 0.7375 1.4061 0.3711 0.099 Uiso 1 calc R . .
C33 C 0.7571(12) 1.4888(8) 0.4560(7) 0.098(4) Uani 1 d . . .
H33 H 0.8130 1.5443 0.4394 0.118 Uiso 1 calc R . .
C34 C 0.7186(13) 1.4899(10) 0.5186(6) 0.098(4) Uani 1 d . . .
H34 H 0.7467 1.5459 0.5460 0.117 Uiso 1 calc R . .
C35 C 0.6385(13) 1.4087(10) 0.5415(6) 0.096(3) Uani 1 d . . .
H35 H 0.6101 1.4112 0.5850 0.115 Uiso 1 calc R . .
C36 C 0.5971(9) 1.3241(7) 0.5051(4) 0.058(2) Uani 1 d . . .
H36 H 0.5430 1.2693 0.5235 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 118.1(3) . . y
N2 P1 C11 109.7(3) . . y
N1 P1 C11 109.7(3) . . y
N2 P1 C1 109.2(4) . . y
N1 P1 C1 107.4(4) . . y
C11 P1 C1 101.5(3) . . y
N2 P2 N3 117.6(3) . . y
N2 P2 C21 107.0(4) . . y
N3 P2 C21 109.4(4) . . y
N2 P2 C2 108.0(4) . . y
N3 P2 C2 107.3(4) . . y
C21 P2 C2 107.0(4) . . y
N3 P3 N1 117.3(3) . . y
N3 P3 C3 108.6(4) . . y
N1 P3 C3 107.7(4) . . y
N3 P3 C31 109.9(3) . . y
N1 P3 C31 108.9(3) . . y
C3 P3 C31 103.7(3) . . y
P3 N1 P1 121.1(4) . . y
P2 N2 P1 122.0(4) . . y
P3 N3 P2 122.4(4) . . y
P1 C1 Br1 111.4(4) . . y
C12 C11 C16 118.5(7) . . ?
C12 C11 P1 120.2(6) . . ?
C16 C11 P1 121.1(6) . . ?
C11 C12 C13 119.9(8) . . ?
C14 C13 C12 120.1(8) . . ?
C13 C14 C15 120.6(8) . . ?
C16 C15 C14 119.0(8) . . ?
C15 C16 C11 121.9(8) . . ?
C26 C21 C22 117.5(8) . . ?
C26 C21 P2 120.9(6) . . ?
C22 C21 P2 121.6(7) . . ?
C23 C22 C21 121.4(10) . . ?
C22 C23 C24 119.0(11) . . ?
C25 C24 C23 119.9(11) . . ?
C26 C25 C24 120.5(10) . . ?
C25 C26 C21 121.7(8) . . ?
C36 C31 C32 117.7(4) . . ?
C36 C31 P3 121.6(5) . . ?
C32 C31 P3 120.74(17) . . ?
C31 C32 C33 120.4(6) . . ?
C34 C33 C32 120.2(10) . . ?
C33 C34 C35 118.9(11) . . ?
C34 C35 C36 123.7(11) . . ?
C35 C36 C31 119.0(9) . . ?
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 1.591(6) . y
P1 N1 1.602(6) . y
P1 C11 1.809(7) . y
P1 C1 1.828(7) . y
P2 N2 1.590(6) . y
P2 N3 1.601(6) . y
P2 C21 1.780(8) . y
P2 C2 1.802(9) . y
P3 N3 1.589(6) . y
P3 N1 1.598(6) . y
P3 C3 1.802(8) . y
P3 C31 1.809(6) . y
Br1 C1 1.926(7) . y
C11 C12 1.378(10) . ?
C11 C16 1.382(10) . ?
C12 C13 1.385(11) . ?
C13 C14 1.366(12) . ?
C14 C15 1.374(11) . ?
C15 C16 1.362(11) . ?
C21 C26 1.377(9) . ?
C21 C22 1.409(12) . ?
C22 C23 1.368(13) . ?
C23 C24 1.397(16) . ?
C24 C25 1.371(16) . ?
C25 C26 1.360(14) . ?
C31 C36 1.384(9) . ?
C31 C32 1.3860 . ?
C32 C33 1.393(12) . ?
C33 C34 1.331(14) . ?
C34 C35 1.344(15) . ?
C35 C36 1.347(13) . ?
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 173.3(4) . . . . ?
N1 P1 C1 Br1 -71.6(4) . . . . ?
