#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/43/2104368.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_2104368
loop_
_publ_author_name
'Coles, Simon'
'Davies, David'
'Hursthouse, Michael'
'Yeşilot, Serkan'
'Çoşut, Bünyemin'
'Kılıç, Adem'
_publ_section_title
;
 Absolute structure determination as a reference for the enantiomeric
 resolution of racemic mixtures of cyclophosphazenes via chiral
 high-performance liquid chromatography
;
_journal_coeditor_code           RY5024
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              355
_journal_page_last               362
_journal_paper_doi               10.1107/S0108768109006120
_journal_volume                  65
_journal_year                    2009
_chemical_formula_sum            'C18 H24 N5 O2 P3 S2'
_chemical_formula_weight         499.45
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           76
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.49120(10)
_cell_length_b                   11.49120(10)
_cell_length_c                   16.7890(2)
_cell_measurement_reflns_used    25190
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2216.95(4)
_computing_cell_refinement       'DENZO, COLLECT'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_data_reduction        'DENZO, COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            41619
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.49
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_T_max  0.8302
_exptl_absorpt_correction_T_min  0.8118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.267
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         5057
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0188
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0283P)²+0.4819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0491
_refine_ls_wR_factor_ref         0.0494
_reflns_number_gt                4976
_reflns_number_total             5057
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ry5024.cif
_cod_data_source_block           3a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P4(1)
_cod_database_code               2104368
_cod_database_fobs_code          2104368
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.82968(12) 0.70919(12) -0.03729(9) 0.0140(3) Uani d . 1 . .
C C2 0.84909(14) 0.70813(13) -0.11901(9) 0.0213(3) Uani d . 1 . .
H H2 0.7906 0.6799 -0.1540 0.026 Uiso calc R 1 . .
C C3 0.95378(15) 0.74816(14) -0.14949(11) 0.0279(4) Uani d . 1 . .
H H3 0.9674 0.7470 -0.2053 0.033 Uiso calc R 1 . .
C C4 1.03848(14) 0.78984(15) -0.09813(13) 0.0323(4) Uani d . 1 . .
H H4 1.1100 0.8180 -0.1190 0.039 Uiso calc R 1 . .
C C5 1.01959(14) 0.79083(14) -0.01660(12) 0.0298(4) Uani d . 1 . .
H H5 1.0786 0.8186 0.0182 0.036 Uiso calc R 1 . .
C C6 0.91472(13) 0.75134(12) 0.01447(10) 0.0204(3) Uani d . 1 . .
H H6 0.9011 0.7530 0.0703 0.024 Uiso calc R 1 . .
C C7 0.83701(13) 0.29119(12) -0.05502(8) 0.0167(3) Uani d . 1 . .
C C8 0.95653(13) 0.29214(13) -0.06857(9) 0.0218(3) Uani d . 1 . .
H H8 0.9924 0.3590 -0.0910 0.026 Uiso calc R 1 . .
C C9 1.02309(14) 0.19564(15) -0.04931(11) 0.0270(3) Uani d . 1 . .
H H9 1.1047 0.1963 -0.0584 0.032 Uiso calc R 1 . .
C C10 0.97048(16) 0.09819(14) -0.01675(10) 0.0286(4) Uani d . 1 . .
H H10 1.0162 0.0321 -0.0034 0.034 Uiso calc R 1 . .
C C11 0.85125(15) 0.09674(14) -0.00354(10) 0.0274(3) Uani d . 1 . .
H H11 0.8157 0.0295 0.0187 0.033 Uiso calc R 1 . .
C C12 0.78345(14) 0.19330(14) -0.02264(9) 0.0226(3) Uani d . 1 . .
H H12 0.7018 0.1924 -0.0137 0.027 Uiso calc R 1 . .
C C13 1.06017(12) 0.55367(13) 0.19484(10) 0.0198(3) Uani d . 1 . .
H H13A 1.0897 0.6045 0.2379 0.024 Uiso calc R 1 . .
H H13B 1.0461 0.6026 0.1473 0.024 Uiso calc R 1 . .
C C14 1.15054(12) 0.46183(13) 0.17538(9) 0.0195(3) Uani d . 1 . .
H H14A 1.1703 0.4185 0.2245 0.023 Uiso calc R 1 . .
H H14B 1.2222 0.5005 0.1561 0.023 Uiso calc R 1 . .
C C15 1.10837(12) 0.37624(13) 0.11235(9) 0.0179(3) Uani d . 1 . .
H H15A 1.0932 0.4178 0.0617 0.021 Uiso calc R 1 . .
H H15B 1.1687 0.3165 0.1025 0.021 Uiso calc R 1 . .
C C16 0.48367(12) 0.21635(12) 0.14389(9) 0.0162(3) Uani d . 1 . .
H H16A 0.4673 0.1319 0.1401 0.019 Uiso calc R 1 . .
H H16B 0.4578 0.2534 0.0937 0.019 Uiso calc R 1 . .
C C17 0.41647(12) 0.26789(12) 0.21348(9) 0.0164(3) Uani d . 1 . .
H H17A 0.4364 0.2249 0.2627 0.020 Uiso calc R 1 . .
H H17B 0.3320 0.2584 0.2039 0.020 Uiso calc R 1 . .
C C18 0.44380(12) 0.39665(12) 0.22502(9) 0.0163(3) Uani d . 1 . .
H H18A 0.4192 0.4411 0.1774 0.020 Uiso calc R 1 . .
H H18B 0.4006 0.4270 0.2716 0.020 Uiso calc R 1 . .
N N1 0.86791(10) 0.48911(10) 0.07770(7) 0.0130(2) Uani d . 1 . .
N N2 0.78575(10) 0.35315(10) 0.19822(7) 0.0135(2) Uani d . 1 . .
N N3 0.63816(10) 0.43377(10) 0.08397(7) 0.0144(2) Uani d . 1 . .
N N4 0.99934(10) 0.31974(10) 0.14119(7) 0.0143(2) Uani d D 1 . .
N N5 0.57020(10) 0.41122(10) 0.23778(7) 0.0133(2) Uani d D 1 . .
O O1 0.95170(8) 0.49992(9) 0.21982(6) 0.0155(2) Uani d . 1 . .
O O2 0.60888(8) 0.23459(8) 0.15424(6) 0.01375(19) Uani d . 1 . .
P P1 0.74443(3) 0.48918(3) 0.03601(2) 0.01101(7) Uani d . 1 . .
P P2 0.89259(3) 0.41507(3) 0.156756(19) 0.01033(7) Uani d . 1 . .
P P3 0.65592(3) 0.36334(3) 0.166283(19) 0.01027(7) Uani d . 1 . .
S S1 0.69478(3) 0.65851(3) 0.00226(2) 0.01505(7) Uani d . 1 . .
S S2 0.75390(3) 0.41789(3) -0.07875(2) 0.01936(8) Uani d . 1 . .
H H4N 0.9798(15) 0.2640(10) 0.1107(8) 0.016(4) Uiso d D 1 . .
H H5N 0.5911(16) 0.4761(8) 0.2574(11) 0.027(5) Uiso d D 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'
O O 0.0106 0.0060 '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_
_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
_geom_angle_publ_flag
C2 C1 C6 . . 120.37(14) ?
C2 C1 S1 . . 120.26(12) ?
C6 C1 S1 . . 119.36(11) ?
C3 C2 C1 . . 120.05(16) ?
C2 C3 C4 . . 119.65(16) ?
C5 C4 C3 . . 120.49(16) ?
C4 C5 C6 . . 120.27(16) ?
C5 C6 C1 . . 119.16(15) ?
C8 C7 C12 . . 120.40(14) ?
C8 C7 S2 . . 118.99(11) ?
C12 C7 S2 . . 120.61(12) ?
C9 C8 C7 . . 120.01(14) ?
C8 C9 C10 . . 119.89(15) ?
C9 C10 C11 . . 120.24(16) ?
C10 C11 C12 . . 120.37(15) ?
C7 C12 C11 . . 119.08(15) ?
O1 C13 C14 . . 110.73(11) ?
C13 C14 C15 . . 112.40(11) ?
N4 C15 C14 . . 108.82(12) ?
O2 C16 C17 . . 110.61(11) ?
C16 C17 C18 . . 111.77(12) ?
N5 C18 C17 . . 109.32(11) ?
P1 N1 P2 . . 121.71(7) ?
P2 N2 P3 . . 123.18(7) ?
P1 N3 P3 . . 122.37(7) ?
C15 N4 P2 . . 112.53(9) ?
C18 N5 P3 . . 116.37(9) ?
C13 O1 P2 . . 115.76(9) ?
C16 O2 P3 . . 118.88(8) ?
N1 P1 N3 . . 117.58(6) ?
N1 P1 S2 . . 111.09(5) ?
N3 P1 S2 . . 110.34(5) ?
N1 P1 S1 . . 111.25(5) ?
N3 P1 S1 . . 107.29(5) ?
S2 P1 S1 . . 97.35(2) ?
N2 P2 O1 . . 108.32(6) ?
N2 P2 N1 . . 117.81(6) ?
O1 P2 N1 . . 107.54(6) ?
N2 P2 N4 . . 110.19(6) ?
O1 P2 N4 . . 101.13(6) ?
N1 P2 N4 . . 110.47(6) ?
O2 P3 N2 . . 107.08(6) ?
O2 P3 N3 . . 108.37(6) ?
N2 P3 N3 . . 116.38(6) ?
O2 P3 N5 . . 101.56(6) ?
N2 P3 N5 . . 109.88(6) ?
N3 P3 N5 . . 112.38(6) ?
C1 S1 P1 . . 99.58(5) ?
C7 S2 P1 . . 98.12(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.390(2) ?
C1 C6 . 1.395(2) ?
C1 S1 . 1.7841(14) ?
C2 C3 . 1.386(2) ?
C3 C4 . 1.386(3) ?
C4 C5 . 1.386(3) ?
C5 C6 . 1.389(2) ?
C7 C8 . 1.392(2) ?
C7 C12 . 1.393(2) ?
C7 S2 . 1.7861(15) ?
C8 C9 . 1.385(2) ?
C9 C10 . 1.385(3) ?
C10 C11 . 1.388(3) ?
C11 C12 . 1.393(2) ?
C13 O1 . 1.4529(17) ?
C13 C14 . 1.516(2) ?
C14 C15 . 1.524(2) ?
C15 N4 . 1.4919(17) ?
C16 O2 . 1.4643(16) ?
C16 C17 . 1.521(2) ?
C17 C18 . 1.5249(19) ?
C18 N5 . 1.4777(17) ?
N1 P1 . 1.5821(11) ?
N1 P2 . 1.6019(12) ?
N2 P2 . 1.5805(12) ?
N2 P3 . 1.5896(11) ?
N3 P1 . 1.5954(12) ?
N3 P3 . 1.6144(12) ?
N4 P2 . 1.6653(12) ?
N5 P3 . 1.6474(12) ?
O1 P2 . 1.5916(10) ?
O2 P3 . 1.5881(9) ?
P1 S2 . 2.0964(5) ?
P1 S1 . 2.1054(5) ?
