#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/57/2215757.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_2215757
loop_
_publ_author_name
'Xuemei Chen'
'Wensheng Xiao'
'Ping Jiao'
_publ_section_title
;
 1,4-Bis(5,5-dimethyl-2-oxo-4-phenyl-1,3,2-dioxaphosphorinan-2-yl)piperazine
;
_journal_coeditor_code           BG2110
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4271
_journal_page_last               o4271
_journal_paper_doi               10.1107/S1600536807048349
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C26 H36 N2 O6 P2'
_chemical_formula_moiety         'C26 H36 N2 O6 P2'
_chemical_formula_sum            'C26 H36 N2 O6 P2'
_chemical_formula_weight         534.51
_chemical_name_systematic
;
1,4-Bis(5,5-dimethyl-2-oxo-4-phenyl-1,3,2-dioxaphosphorinan-2-yl)piperazine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                65.680(2)
_cell_angle_beta                 86.755(2)
_cell_angle_gamma                72.641(2)
_cell_formula_units_Z            1
_cell_length_a                   6.4436(7)
_cell_length_b                   10.4563(11)
_cell_length_c                   11.5762(13)
_cell_measurement_reflns_used    1049
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      19.96
_cell_measurement_theta_min      2.28
_cell_volume                     676.40(13)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  'SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0630
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7086
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.9505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0717P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1507
_reflns_number_gt                1754
_reflns_number_total             2616
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2110.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_cell_volume        676.40(18)
_cod_database_code               2215757
_cod_database_fobs_code          2215757
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.8132(4) 0.8979(3) 0.2863(3) 0.0363(7) Uani d . 1
C C2 0.7646(5) 0.9464(4) 0.3830(3) 0.0539(9) Uani d . 1
H H2 0.8259 0.8852 0.4654 0.065 Uiso calc R 1
C C3 0.6243(6) 1.0863(4) 0.3556(4) 0.0690(11) Uani d . 1
H H3 0.5952 1.1192 0.4200 0.083 Uiso calc R 1
C C4 0.5276(6) 1.1771(4) 0.2359(4) 0.0685(11) Uani d . 1
H H4 0.4326 1.2703 0.2192 0.082 Uiso calc R 1
C C5 0.5726(5) 1.1291(3) 0.1405(3) 0.0578(9) Uani d . 1
H H5 0.5079 1.1899 0.0588 0.069 Uiso calc R 1
C C6 0.7137(5) 0.9904(3) 0.1661(3) 0.0441(8) Uani d . 1
H H6 0.7423 0.9586 0.1011 0.053 Uiso calc R 1
C C7 0.9697(4) 0.7486(3) 0.3152(2) 0.0353(7) Uani d . 1
H H7 0.9530 0.6826 0.4022 0.042 Uiso calc R 1
C C8 1.2127(5) 0.7404(3) 0.3031(3) 0.0403(7) Uani d . 1
C C9 1.2908(5) 0.7813(4) 0.4025(3) 0.0565(9) Uani d . 1
H H9A 1.4460 0.7625 0.4026 0.085 Uiso calc R 1
H H9B 1.2541 0.7231 0.4851 0.085 Uiso calc R 1
H H9C 1.2211 0.8838 0.3819 0.085 Uiso calc R 1
C C10 1.2518(5) 0.8427(4) 0.1706(3) 0.0517(9) Uani d . 1
H H10A 1.1765 0.9430 0.1558 0.078 Uiso calc R 1
H H10B 1.1983 0.8196 0.1082 0.078 Uiso calc R 1
H H10C 1.4052 0.8301 0.1644 0.078 Uiso calc R 1
C C11 1.3430(5) 0.5815(4) 0.3337(3) 0.0519(9) Uani d . 1
H H11A 1.4967 0.5736 0.3281 0.062 Uiso calc R 1
H H11B 1.3227 0.5200 0.4203 0.062 Uiso calc R 1
C C12 0.8516(5) 0.4487(3) 0.0935(3) 0.0468(8) Uani d . 1
H H12A 0.7105 0.5178 0.0542 0.056 Uiso calc R 1
H H12B 0.8300 0.3779 0.1758 0.056 Uiso calc R 1
C C13 1.0454(5) 0.6299(3) -0.0110(3) 0.0474(8) Uani d . 1
H H13A 1.1448 0.6754 0.0054 0.057 Uiso calc R 1
H H13B 0.9129 0.7072 -0.0553 0.057 Uiso calc R 1
N N1 0.9939(4) 0.5274(3) 0.1097(2) 0.0446(7) Uani d . 1
O O6 1.2784(3) 0.5277(2) 0.2478(2) 0.0523(6) Uani d . 1
O O7 0.9065(3) 0.69522(19) 0.22708(16) 0.0366(5) Uani d . 1
O O8 0.9706(4) 0.4198(2) 0.35255(19) 0.0615(7) Uani d . 1
P P1 1.03157(13) 0.53246(8) 0.24428(7) 0.0406(3) 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 0.0000 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
C6 C1 C2 . . 118.4(3)
C6 C1 C7 . . 122.1(2)
C2 C1 C7 . . 119.5(3)
C3 C2 C1 . . 119.6(3)
C3 C2 H2 . . 120.2
C1 C2 H2 . . 120.2
C4 C3 C2 . . 121.3(3)
C4 C3 H3 . . 119.3
C2 C3 H3 . . 119.3
C3 C4 C5 . . 119.3(3)
C3 C4 H4 . . 120.3
C5 C4 H4 . . 120.3
C4 C5 C6 . . 120.0(3)
C4 C5 H5 . . 120.0
C6 C5 H5 . . 120.0
C1 C6 C5 . . 121.3(3)
C1 C6 H6 . . 119.3
C5 C6 H6 . . 119.3
O7 C7 C1 . . 107.3(2)
O7 C7 C8 . . 108.33(19)
C1 C7 C8 . . 116.0(2)
O7 C7 H7 . . 108.3
C1 C7 H7 . . 108.3
C8 C7 H7 . . 108.3
C11 C8 C10 . . 111.0(2)
C11 C8 C9 . . 107.0(2)
C10 C8 C9 . . 109.4(2)
C11 C8 C7 . . 107.8(2)
C10 C8 C7 . . 111.6(2)
C9 C8 C7 . . 109.9(2)
C8 C9 H9A . . 109.5
C8 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
C8 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
C8 C10 H10A . . 109.5
C8 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C8 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
O6 C11 C8 . . 112.3(2)
O6 C11 H11A . . 109.1
C8 C11 H11A . . 109.1
O6 C11 H11B . . 109.1
C8 C11 H11B . . 109.1
H11A C11 H11B . . 107.9
N1 C12 C13 . 2_765 109.5(2)
N1 C12 H12A . . 109.8
C13 C12 H12A 2_765 . 109.8
N1 C12 H12B . . 109.8
C13 C12 H12B 2_765 . 109.8
H12A C12 H12B . . 108.2
N1 C13 C12 . 2_765 110.8(2)
N1 C13 H13A . . 109.5
C12 C13 H13A 2_765 . 109.5
N1 C13 H13B . . 109.5
C12 C13 H13B 2_765 . 109.5
H13A C13 H13B . . 108.1
C13 N1 C12 . . 113.1(2)
C13 N1 P1 . . 123.04(18)
C12 N1 P1 . . 121.8(2)
C11 O6 P1 . . 116.17(17)
C7 O7 P1 . . 118.41(16)
O8 P1 O6 . . 115.83(13)
O8 P1 O7 . . 113.86(12)
O6 P1 O7 . . 102.54(10)
O8 P1 N1 . . 114.05(12)
O6 P1 N1 . . 103.11(12)
O7 P1 N1 . . 106.11(11)
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
P1 N1 . 1.615(2) yes
P1 O6 . 1.578(2) yes
P1 O7 . 1.583(2) yes
P1 O8 . 1.455(2) yes
C1 C6 . 1.380(4) ?
C1 C2 . 1.392(3) ?
C1 C7 . 1.495(4) ?
C2 C3 . 1.386(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.368(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.374(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.381(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O7 . 1.473(3) ?
C7 C8 . 1.544(4) ?
C7 H7 . 0.9800 ?
C8 C11 . 1.519(4) ?
C8 C10 . 1.525(4) ?
C8 C9 . 1.536(4) ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 O6 . 1.458(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 N1 . 1.466(4) y
C12 C13 2_765 1.509(4) y
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 N1 . 1.462(4) y
C13 C12 2_765 1.509(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C12 H12B O8 . 0.97 2.53 3.008(4) 111 ?
C9 H9B O8 2_766 0.96 2.56 3.459(4) 157 yes
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_site_symmetry_1
_geom_torsion
C6 C1 C2 C3 . -1.9(5)
C7 C1 C2 C3 . 178.2(3)
C1 C2 C3 C4 . 1.7(5)
C2 C3 C4 C5 . -0.7(6)
C3 C4 C5 C6 . 0.1(5)
C2 C1 C6 C5 . 1.3(5)
C7 C1 C6 C5 . -178.8(3)
C4 C5 C6 C1 . -0.4(5)
C6 C1 C7 O7 . -29.3(3)
C2 C1 C7 O7 . 150.5(2)
C6 C1 C7 C8 . 91.9(3)
C2 C1 C7 C8 . -88.3(3)
O7 C7 C8 C11 . -58.3(3)
C1 C7 C8 C11 . -179.0(2)
O7 C7 C8 C10 . 63.8(3)
C1 C7 C8 C10 . -56.9(3)
O7 C7 C8 C9 . -174.7(2)
C1 C7 C8 C9 . 64.7(3)
C10 C8 C11 O6 . -62.6(3)
C9 C8 C11 O6 . 178.1(2)
C7 C8 C11 O6 . 59.9(3)
C12 C13 N1 C12 2_765 -56.6(4)
C12 C13 N1 P1 2_765 139.4(2)
C13 C12 N1 C13 2_765 55.9(4)
C13 C12 N1 P1 2_765 -139.9(2)
C8 C11 O6 P1 . -58.8(3)
C1 C7 O7 P1 . -174.51(16)
C8 C7 O7 P1 . 59.6(3)
C11 O6 P1 O8 . -75.5(2)
C11 O6 P1 O7 . 49.2(2)
C11 O6 P1 N1 . 159.3(2)
C7 O7 P1 O8 . 74.4(2)
C7 O7 P1 O6 . -51.54(19)
C7 O7 P1 N1 . -159.37(17)
C13 N1 P1 O8 . -179.7(2)
C12 N1 P1 O8 . 17.8(3)
C13 N1 P1 O6 . -53.2(3)
C12 N1 P1 O6 . 144.2(2)
C13 N1 P1 O7 . 54.2(3)
C12 N1 P1 O7 . -108.4(2)
