#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/51/2235199.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_2235199
loop_
_publ_author_name
'Fulfer, Bradford W.'
'Fronczek, Frank R.'
'Watkins, Steven F.'
_publ_section_title
;
 (2R,4R)-4-(2-Ethoxy-2-oxoethyl)-2,6,6-trimethyl--2-oxo-1,3,6,2λ⁵-dioxazaphosphocan-6-ium
 iodide
;
_journal_coeditor_code           PV2538
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1596
_journal_paper_doi               10.1107/S1600536812018466
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H23 N O5 P +, I -'
_chemical_formula_moiety         'C11 H23 N O5 P +, I -'
_chemical_formula_sum            'C11 H23 I N O5 P'
_chemical_formula_weight         407.17
_chemical_name_systematic
;
(2R,4R)-4-(2-Ethoxy-2-oxoethyl)-2,6,6-trimethyl--2-oxo-
1,3,6,2λ⁵-dioxazaphosphocan-6-ium iodide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4882(2)
_cell_length_b                   11.7438(2)
_cell_length_c                   18.0235(4)
_cell_measurement_pressure       101.3
_cell_measurement_reflns_used    3522
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      33.7
_cell_measurement_theta_min      2.5
_cell_volume                     1584.99(6)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Bruker 2004)'
_computing_data_reduction
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997), and
SORTAV (Blessing, 1987, 1989)
;
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            26155
_diffrn_reflns_reduction_process '(SORTAV; Blessing, 1987, 1989)'
_diffrn_reflns_theta_full        33.72
_diffrn_reflns_theta_max         33.72
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    2.136
_exptl_absorpt_correction_T_max  0.7400
_exptl_absorpt_correction_T_min  0.5912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.66
_refine_ls_abs_structure_details 'Flack (1983), 2741 Friedel pairs'
_refine_ls_abs_structure_Flack   0.006(7)
_refine_ls_extinction_coef       0.0037(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     177
_refine_ls_number_reflns         6304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_gt           0.016
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0158P)²+0.6491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0386
_reflns_number_gt                6235
_reflns_number_total             6304
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2538.cif
_cod_data_source_block           I
_cod_database_code               2235199
_cod_database_fobs_code          2235199
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
I I1 0.043921(11) 0.959574(7) 0.228805(4) 0.01449(2) Uani d . 1
C C1 0.36047(17) 0.73826(11) 0.14505(7) 0.0118(2) Uani d . 1
H H1A 0.4184 0.762 0.0982 0.014 Uiso calc R 1
H H1B 0.3399 0.808 0.1747 0.014 Uiso calc R 1
C C2 0.17996(17) 0.68738(12) 0.12605(7) 0.0127(2) Uani d . 1
H H2A 0.122 0.662 0.1726 0.015 Uiso calc R 1
H H2B 0.1042 0.7478 0.1042 0.015 Uiso calc R 1
C C3 0.59764(16) 0.56554(10) 0.06758(7) 0.0098(2) Uani d . 1
H H3 0.6129 0.6486 0.0573 0.012 Uiso calc R 1
C C4 0.53465(16) 0.55152(10) 0.14844(6) 0.01054(18) Uani d . 1
H H4A 0.4272 0.5024 0.149 0.013 Uiso calc R 1
H H4B 0.6293 0.5121 0.1769 0.013 Uiso calc R 1
C C5 0.66050(17) 0.73081(11) 0.19789(7) 0.0135(2) Uani d . 1
H H5A 0.6346 0.7997 0.2266 0.02 Uiso calc R 1
H H5B 0.7092 0.7522 0.1494 0.02 Uiso calc R 1
H H5C 0.7479 0.6842 0.2246 0.02 Uiso calc R 1
C C6 0.41775(17) 0.63424(12) 0.26270(7) 0.0157(2) Uani d . 1
H H6A 0.5067 0.59 0.2903 0.024 Uiso calc R 1
H H6B 0.3084 0.5892 0.2572 0.024 Uiso calc R 1
H H6C 0.3908 0.7045 0.2898 0.024 Uiso calc R 1
C C7 0.17486(17) 0.50423(12) -0.06268(7) 0.0133(2) Uani d . 1
H H7A 0.0611 0.54 -0.0761 0.02 Uiso calc R 1
H H7B 0.1518 0.431 -0.0385 0.02 Uiso calc R 1
H H7C 0.2462 0.4919 -0.1075 0.02 Uiso calc R 1
C C8 0.77289(16) 0.50631(11) 0.05177(7) 0.0119(2) Uani d . 1
H H8A 0.7942 0.5088 -0.0024 0.014 Uiso calc R 1
H H8B 0.8696 0.5504 0.0758 0.014 Uiso calc R 1
C C9 0.78769(17) 0.38388(11) 0.07689(7) 0.0118(2) Uani d . 1
C C10 1.00454(18) 0.23653(11) 0.09371(9) 0.0171(2) Uani d . 1
H H10A 0.964 0.1762 0.0592 0.021 Uiso calc R 1
H H10B 0.9495 0.223 0.1429 0.021 Uiso calc R 1
C C11 1.2050(2) 0.23625(13) 0.09977(8) 0.0180(2) Uani d . 1
H H11A 1.2573 0.2507 0.0508 0.027 Uiso calc R 1
H H11B 1.2453 0.162 0.118 0.027 Uiso calc R 1
H H11C 1.2429 0.2959 0.1344 0.027 Uiso calc R 1
N N1 0.49050(13) 0.66341(9) 0.18714(6) 0.01052(17) Uani d . 1
O O1 0.46590(12) 0.52051(7) 0.01612(4) 0.01006(14) Uani d . 1
O O2 0.18599(12) 0.59216(8) 0.07507(5) 0.01138(16) Uani d . 1
O O3 0.32941(13) 0.71123(8) -0.02761(5) 0.01296(17) Uani d . 1
O O4 0.66875(13) 0.32687(9) 0.10299(6) 0.01603(18) Uani d . 1
O O5 0.95505(14) 0.34845(8) 0.06562(5) 0.01394(16) Uani d . 1
P P1 0.29315(4) 0.59443(3) -0.001033(16) 0.00900(5) Uani 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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 0.006 '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
N1 C1 C2 117.20(10)
N1 C1 H1A 108
C2 C1 H1A 108
N1 C1 H1B 108
C2 C1 H1B 108
H1A C1 H1B 107.2
O2 C2 C1 114.81(10)
O2 C2 H2A 108.6
C1 C2 H2A 108.6
O2 C2 H2B 108.6
C1 C2 H2B 108.6
H2A C2 H2B 107.5
O1 C3 C8 107.54(10)
O1 C3 C4 110.91(9)
C8 C3 C4 113.25(10)
O1 C3 H3 108.3
C8 C3 H3 108.3
C4 C3 H3 108.3
N1 C4 C3 114.03(9)
N1 C4 H4A 108.7
C3 C4 H4A 108.7
N1 C4 H4B 108.7
C3 C4 H4B 108.7
H4A C4 H4B 107.6
N1 C5 H5A 109.5
N1 C5 H5B 109.5
H5A C5 H5B 109.5
N1 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
N1 C6 H6A 109.5
N1 C6 H6B 109.5
H6A C6 H6B 109.5
N1 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
P1 C7 H7A 109.5
P1 C7 H7B 109.5
H7A C7 H7B 109.5
P1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 C3 116.40(10)
C9 C8 H8A 108.2
C3 C8 H8A 108.2
C9 C8 H8B 108.2
C3 C8 H8B 108.2
H8A C8 H8B 107.3
O4 C9 O5 125.27(12)
O4 C9 C8 126.10(12)
O5 C9 C8 108.63(11)
O5 C10 C11 106.31(11)
O5 C10 H10A 110.5
C11 C10 H10A 110.5
O5 C10 H10B 110.5
C11 C10 H10B 110.5
H10A C10 H10B 108.7
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C6 N1 C5 107.93(9)
C6 N1 C1 110.62(10)
C5 N1 C1 107.55(10)
C6 N1 C4 107.23(9)
C5 N1 C4 109.11(9)
C1 N1 C4 114.23(9)
C3 O1 P1 118.56(7)
C2 O2 P1 123.39(8)
C9 O5 C10 117.83(11)
O3 P1 O1 114.88(5)
O3 P1 O2 112.83(5)
O1 P1 O2 103.53(5)
O3 P1 C7 116.32(6)
O1 P1 C7 101.68(6)
O2 P1 C7 106.18(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.5153(16)
C1 C2 1.5170(18)
C1 H1A 0.99
C1 H1B 0.99
C2 O2 1.4481(16)
C2 H2A 0.99
C2 H2B 0.99
C3 O1 1.4536(15)
C3 C8 1.5123(17)
C3 C4 1.5407(16)
C3 H3 1
C4 N1 1.5239(15)
C4 H4A 0.99
C4 H4B 0.99
C5 N1 1.5115(16)
C5 H5A 0.98
C5 H5B 0.98
C5 H5C 0.98
C6 N1 1.5063(16)
C6 H6A 0.98
C6 H6B 0.98
C6 H6C 0.98
C7 P1 1.7723(13)
C7 H7A 0.98
C7 H7B 0.98
C7 H7C 0.98
C8 C9 1.5115(18)
C8 H8A 0.99
C8 H8B 0.99
C9 O4 1.2095(16)
C9 O5 1.3361(16)
C10 O5 1.4565(16)
C10 C11 1.505(2)
C10 H10A 0.99
C10 H10B 0.99
C11 H11A 0.98
C11 H11B 0.98
C11 H11C 0.98
O1 P1 1.5883(9)
O2 P1 1.5893(9)
O3 P1 1.4780(10)
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_publ_flag
O2 P1 O1 C3 -68.45(9) y
P1 O1 C3 C4 77.51(10) y
O1 C3 C4 N1 -111.53(11) y
C3 C4 N1 C1 52.59(13) y
C4 N1 C1 C2 57.38(13) y
N1 C1 C2 O2 -64.93(14) y
C1 C2 O2 P1 -49.45(14) y
C2 O2 P1 O1 103.91(10) y
C8 C3 C4 N1 127.45(11) ?
O1 C3 C8 C9 -73.74(13) ?
C4 C3 C8 C9 49.16(14) ?
C3 C8 C9 O4 6.12(19) ?
C3 C8 C9 O5 -173.79(11) ?
C2 C1 N1 C6 -63.71(13) ?
C2 C1 N1 C5 178.65(10) ?
C3 C4 N1 C6 175.54(10) ?
C3 C4 N1 C5 -67.81(12) ?
C8 C3 O1 P1 -158.16(8) ?
O4 C9 O5 C10 -6.70(19) ?
C8 C9 O5 C10 173.21(11) ?
C11 C10 O5 C9 -159.32(12) ?
C3 O1 P1 O3 55.03(9) ?
C3 O1 P1 C7 -178.47(9) ?
C2 O2 P1 O3 -20.90(11) ?
C2 O2 P1 C7 -149.44(10) ?
