#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/43/2104371.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_2104371
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_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 O4 P3'
_chemical_formula_weight         467.33
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           145
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_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                120.00
_cell_formula_units_Z            3
_cell_length_a                   10.49200(10)
_cell_length_b                   10.49200(10)
_cell_length_c                   16.6645(3)
_cell_measurement_reflns_used    2347
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1588.69(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, 1990)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4871
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.32
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.8998
_exptl_absorpt_correction_T_min  0.8575
_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    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.383
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4848
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0389P)²+0.8904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0715
_reflns_number_gt                4802
_reflns_number_total             4848
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ry5024.cif
_cod_data_source_block           5a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal' 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 'Trigonal' changed to 'trigonal'
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      P3(2)
_cod_database_code               2104371
_cod_database_fobs_code          2104371
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
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 0.5989(3) 1.0664(3) 0.99501(16) 0.0175(5) Uani d . 1 . .
C C2 0.6981(3) 1.2019(3) 0.96413(18) 0.0249(6) Uani d . 1 . .
H H2 0.6980 1.2215 0.9085 0.030 Uiso calc R 1 . .
C C3 0.7981(4) 1.3094(4) 1.0152(2) 0.0316(7) Uani d . 1 . .
H H3 0.8664 1.4039 0.9947 0.038 Uiso calc R 1 . .
C C4 0.7987(4) 1.2796(4) 1.0961(2) 0.0315(7) Uani d . 1 . .
H H4 0.8672 1.3540 1.1310 0.038 Uiso calc R 1 . .
C C5 0.7003(4) 1.1423(4) 1.12636(18) 0.0302(7) Uani d . 1 . .
H H5 0.7020 1.1220 1.1818 0.036 Uiso calc R 1 . .
C C6 0.5991(3) 1.0343(3) 1.07577(18) 0.0251(6) Uani d . 1 . .
H H6 0.5309 0.9396 1.0961 0.030 Uiso calc R 1 . .
C C7 0.3613(3) 0.6262(3) 0.81817(16) 0.0148(5) Uani d . 1 . .
C C8 0.3212(3) 0.4953(3) 0.85581(17) 0.0232(6) Uani d . 1 . .
H H8 0.3098 0.4869 0.9125 0.028 Uiso calc R 1 . .
C C9 0.2974(4) 0.3749(3) 0.80942(19) 0.0277(7) Uani d . 1 . .
H H9 0.2696 0.2834 0.8346 0.033 Uiso calc R 1 . .
C C10 0.3140(3) 0.3878(3) 0.72724(18) 0.0218(6) Uani d . 1 . .
H H10 0.2991 0.3058 0.6960 0.026 Uiso calc R 1 . .
C C11 0.3523(3) 0.5202(3) 0.69040(16) 0.0235(6) Uani d . 1 . .
H H11 0.3621 0.5285 0.6337 0.028 Uiso calc R 1 . .
C C12 0.3765(3) 0.6414(3) 0.73619(16) 0.0221(6) Uani d . 1 . .
H H12 0.4029 0.7328 0.7113 0.026 Uiso calc R 1 . .
C C13 0.6087(3) 0.5161(3) 1.02805(18) 0.0235(6) Uani d . 1 . .
H H13A 0.5877 0.4137 1.0209 0.028 Uiso calc R 1 . .
H H13B 0.5137 0.5148 1.0285 0.028 Uiso calc R 1 . .
C C14 0.6869(4) 0.5755(4) 1.10715(19) 0.0261(7) Uani d . 1 . .
H H14A 0.7762 0.5662 1.1087 0.031 Uiso calc R 1 . .
H H14B 0.6215 0.5154 1.1514 0.031 Uiso calc R 1 . .
C C15 0.7306(3) 0.7351(4) 1.12042(16) 0.0231(6) Uani d . 1 . .
H H15A 0.6414 0.7437 1.1264 0.028 Uiso calc R 1 . .
H H15B 0.7894 0.7718 1.1702 0.028 Uiso calc R 1 . .
N N4 0.8183(3) 0.8242(3) 1.05117(13) 0.0173(5) Uani d D 1 . .
C C16 0.9219(3) 1.1999(3) 0.76421(16) 0.0200(6) Uani d . 1 . .
H H16A 1.0010 1.3035 0.7705 0.024 Uiso calc R 1 . .
H H16B 0.8261 1.1966 0.7674 0.024 Uiso calc R 1 . .
C C17 0.9363(3) 1.1422(3) 0.68278(17) 0.0221(6) Uani d . 1 . .
H H17A 0.9231 1.2000 0.6400 0.027 Uiso calc R 1 . .
H H17B 1.0367 1.1568 0.6775 0.027 Uiso calc R 1 . .
C C18 0.8257(3) 0.9813(3) 0.67088(15) 0.0207(6) Uani d . 1 . .
H H18A 0.7250 0.9669 0.6698 0.025 Uiso calc R 1 . .
H H18B 0.8440 0.9474 0.6189 0.025 Uiso calc R 1 . .
N N5 0.8383(3) 0.8942(3) 0.73720(13) 0.0160(4) Uani d D 1 . .
N N1 0.5814(2) 0.7685(3) 0.96406(13) 0.0139(4) Uani d . 1 . .
N N2 0.8474(2) 0.8609(3) 0.89470(14) 0.0147(4) Uani d . 1 . .
N N3 0.6528(2) 0.9339(3) 0.83125(13) 0.0151(4) Uani d . 1 . .
O O1 0.4938(2) 0.9583(2) 0.94427(11) 0.0155(4) Uani d . 1 . .
O O2 0.3803(2) 0.7472(2) 0.86408(11) 0.0151(4) Uani d . 1 . .
O O3 0.6979(2) 0.6057(2) 0.96134(11) 0.0178(4) Uani d . 1 . .
O O4 0.9321(2) 1.1113(2) 0.82846(11) 0.0165(4) Uani d . 1 . .
P P1 0.53976(7) 0.85171(7) 0.90071(4) 0.01200(11) Uani d . 1 . .
P P2 0.73541(7) 0.77205(7) 0.96437(3) 0.01212(12) Uani d . 1 . .
P P3 0.80971(7) 0.94302(7) 0.82731(4) 0.01249(12) Uani d . 1 . .
H H5N 0.794(4) 0.8026(13) 0.732(3) 0.041(12) Uiso d D 1 . .
H H4N 0.857(4) 0.9153(14) 1.060(2) 0.035(11) 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'
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 . . 121.5(3) ?
C2 C1 O1 . . 119.6(2) ?
C6 C1 O1 . . 119.0(3) ?
C1 C2 C3 . . 119.1(3) ?
C2 C3 C4 . . 120.2(3) ?
C5 C4 C3 . . 120.3(3) ?
C4 C5 C6 . . 119.9(3) ?
C5 C6 C1 . . 119.0(3) ?
C8 C7 C12 . . 122.1(3) ?
C8 C7 O2 . . 119.3(2) ?
C12 C7 O2 . . 118.6(2) ?
C7 C8 C9 . . 118.7(3) ?
C10 C9 C8 . . 120.4(3) ?
C9 C10 C11 . . 119.9(3) ?
C10 C11 C12 . . 120.2(3) ?
C7 C12 C11 . . 118.7(3) ?
O3 C13 C14 . . 111.0(2) ?
C13 C14 C15 . . 112.7(2) ?
N4 C15 C14 . . 109.5(2) ?
C15 N4 P2 . . 114.82(19) ?
O4 C16 C17 . . 110.3(2) ?
C18 C17 C16 . . 112.8(2) ?
N5 C18 C17 . . 109.6(2) ?
C18 N5 P3 . . 113.47(18) ?
P1 N1 P2 . . 123.40(14) ?
P3 N2 P2 . . 121.82(13) ?
P1 N3 P3 . . 122.32(14) ?
C1 O1 P1 . . 116.74(16) ?
C7 O2 P1 . . 117.07(16) ?
C13 O3 P2 . . 114.37(17) ?
C16 O4 P3 . . 115.24(16) ?
N1 P1 N3 . . 117.27(11) ?
N1 P1 O2 . . 111.37(12) ?
N3 P1 O2 . . 109.89(11) ?
N1 P1 O1 . . 110.52(11) ?
N3 P1 O1 . . 111.13(11) ?
O2 P1 O1 . . 94.31(9) ?
N2 P2 O3 . . 109.11(12) ?
N2 P2 N1 . . 117.16(11) ?
O3 P2 N1 . . 106.41(12) ?
N2 P2 N4 . . 109.75(12) ?
O3 P2 N4 . . 101.20(11) ?
N1 P2 N4 . . 111.92(12) ?
O4 P3 N2 . . 108.37(11) ?
O4 P3 N3 . . 107.64(12) ?
N2 P3 N3 . . 117.90(12) ?
O4 P3 N5 . . 100.61(11) ?
N2 P3 N5 . . 109.91(12) ?
N3 P3 N5 . . 110.93(12) ?
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 . 1.375(4) ?
C1 C6 . 1.388(4) ?
C1 O1 . 1.403(3) ?
C2 C3 . 1.383(4) ?
C3 C4 . 1.386(5) ?
C4 C5 . 1.381(5) ?
C5 C6 . 1.386(4) ?
C7 C8 . 1.370(4) ?
C7 C12 . 1.376(4) ?
C7 O2 . 1.408(3) ?
C8 C9 . 1.393(4) ?
C9 C10 . 1.379(4) ?
C10 C11 . 1.382(4) ?
C11 C12 . 1.393(4) ?
C13 O3 . 1.455(3) ?
C13 C14 . 1.512(5) ?
C14 C15 . 1.514(5) ?
C15 N4 . 1.480(3) ?
N4 P2 . 1.635(2) ?
C16 O4 . 1.456(3) ?
C16 C17 . 1.524(4) ?
C17 C18 . 1.509(4) ?
C18 N5 . 1.482(3) ?
N5 P3 . 1.662(2) ?
N1 P1 . 1.565(2) ?
N1 P2 . 1.597(2) ?
N2 P3 . 1.582(2) ?
N2 P2 . 1.582(2) ?
N3 P1 . 1.571(2) ?
N3 P3 . 1.602(2) ?
O1 P1 . 1.5969(19) ?
O2 P1 . 1.5936(18) ?
O3 P2 . 1.5862(19) ?
O4 P3 . 1.5805(19) ?
