#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/81/2208113.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_2208113
loop_
_publ_author_name
'Chang Liu'
'Yan Yu'
'Xingyu Yang'
_publ_section_title
;
 2-Benzylidenehydrazino-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinane
 2-oxide
;
_journal_coeditor_code           LH6543
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o536
_journal_page_last               o537
_journal_paper_doi               10.1107/S160053680504184X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H21 N2 O3 P'
_chemical_formula_moiety         'C18 H21 N2 O3 P'
_chemical_formula_sum            'C18 H21 N2 O3 P'
_chemical_formula_weight         344.34
_chemical_name_systematic
;
2-Benzylidenehydrazino-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinane 2-oxide
;
_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                 100.568(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5618(9)
_cell_length_b                   17.683(2)
_cell_length_c                   14.9324(17)
_cell_measurement_reflns_used    6100
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      25.98
_cell_measurement_theta_min      2.30
_cell_volume                     1962.8(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16102
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.80
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         4284
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.073P)²+0.3167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1405
_reflns_number_gt                3365
_reflns_number_total             4284
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6543.cif
_cod_data_source_block           I
_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:

'_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2208113
_cod_database_fobs_code          2208113
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_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_type_symbol
C1 -0.0128(3) 0.75010(12) 0.70630(19) 0.0795(7) Uani d . 1 C
H1 -0.0839 0.7660 0.7474 0.095 Uiso calc R 1 H
C2 0.0174(5) 0.79822(16) 0.6373(3) 0.1168(13) Uani d . 1 C
H2 -0.0338 0.8462 0.6321 0.140 Uiso calc R 1 H
C3 0.1220(5) 0.7753(2) 0.5772(3) 0.1243(15) Uani d . 1 C
H3 0.1430 0.8080 0.5314 0.149 Uiso calc R 1 H
C4 0.1957(4) 0.7051(2) 0.58377(18) 0.1016(10) Uani d . 1 C
H4 0.2660 0.6897 0.5421 0.122 Uiso calc R 1 H
C5 0.1670(3) 0.65612(14) 0.65211(14) 0.0666(6) Uani d . 1 C
H5 0.2182 0.6081 0.6561 0.080 Uiso calc R 1 H
C6 0.0630(2) 0.67818(11) 0.71421(13) 0.0528(5) Uani d . 1 C
C7 0.0385(2) 0.62835(10) 0.79211(12) 0.0468(4) Uani d . 1 C
H7 0.0225 0.6610 0.8430 0.056 Uiso calc R 1 H
C8 -0.1182(2) 0.57135(11) 0.77607(13) 0.0533(5) Uani d . 1 C
C9 -0.1059(3) 0.51627(13) 0.69918(15) 0.0686(6) Uani d . 1 C
H9A 0.0069 0.4899 0.7122 0.103 Uiso calc R 1 H
H9B -0.1140 0.5436 0.6430 0.103 Uiso calc R 1 H
H9C -0.2028 0.4805 0.6938 0.103 Uiso calc R 1 H
C10 -0.2975(3) 0.61423(16) 0.75654(18) 0.0862(8) Uani d . 1 C
H10A -0.3951 0.5790 0.7536 0.129 Uiso calc R 1 H
H10B -0.3080 0.6404 0.6994 0.129 Uiso calc R 1 H
H10C -0.3016 0.6501 0.8043 0.129 Uiso calc R 1 H
C11 -0.1129(3) 0.52920(13) 0.86531(14) 0.0634(5) Uani d . 1 C
H11A -0.1287 0.5650 0.9124 0.076 Uiso calc R 1 H
H11B -0.2120 0.4936 0.8583 0.076 Uiso calc R 1 H
C12 0.4547(2) 0.38363(11) 0.77664(12) 0.0515(4) Uani d . 1 C
H12 0.5512 0.3706 0.8221 0.062 Uiso calc R 1 H
C13 0.4305(2) 0.34491(11) 0.68865(12) 0.0513(4) Uani d . 1 C
C14 0.2966(3) 0.36485(16) 0.61591(15) 0.0834(8) Uani d . 1 C
H14 0.2194 0.4047 0.6221 0.100 Uiso calc R 1 H
C15 0.2771(4) 0.32615(19) 0.53471(17) 0.0991(9) Uani d . 1 C
H15 0.1872 0.3402 0.4863 0.119 Uiso calc R 1 H
C16 0.3892(3) 0.26709(16) 0.52479(16) 0.0830(7) Uani d . 1 C
H16 0.3758 0.2412 0.4698 0.100 Uiso calc R 1 H
C17 0.5192(3) 0.24670(14) 0.59504(16) 0.0760(6) Uani d . 1 C
H17 0.5948 0.2064 0.5886 0.091 Uiso calc R 1 H
C18 0.5405(3) 0.28540(12) 0.67635(14) 0.0629(5) Uani d . 1 C
H18 0.6314 0.2709 0.7240 0.076 Uiso calc R 1 H
N1 0.3812(2) 0.46926(9) 0.87674(11) 0.0570(4) Uani d D 1 N
N2 0.3460(2) 0.43469(10) 0.79176(10) 0.0565(4) Uani d . 1 N
O1 0.05506(16) 0.48862(7) 0.89385(8) 0.0540(3) Uani d . 1 O
O2 0.20848(15) 0.58760(7) 0.81882(8) 0.0482(3) Uani d . 1 O
O3 0.30688(17) 0.56563(7) 0.99049(8) 0.0534(3) Uani d . 1 O
P1 0.23943(6) 0.53121(3) 0.90162(3) 0.04369(16) Uani d . 1 P
H1A 0.4739(17) 0.4553(10) 0.9146(10) 0.052 Uiso d D 1 H
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
C2 C1 C6 120.2(3)
C2 C1 H1 119.9
C6 C1 H1 119.9
C3 C2 C1 120.1(3)
C3 C2 H2 119.9
C1 C2 H2 119.9
C4 C3 C2 120.3(3)
C4 C3 H3 119.9
C2 C3 H3 119.9
C3 C4 C5 120.5(3)
C3 C4 H4 119.8
C5 C4 H4 119.8
C6 C5 C4 120.3(2)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C1 118.6(2)
C5 C6 C7 121.57(17)
C1 C6 C7 119.7(2)
O2 C7 C6 105.87(14)
O2 C7 C8 109.41(14)
C6 C7 C8 117.74(15)
O2 C7 H7 107.8
C6 C7 H7 107.8
C8 C7 H7 107.8
C11 C8 C9 110.61(18)
C11 C8 C10 106.83(16)
C9 C8 C10 110.32(18)
C11 C8 C7 106.76(15)
C9 C8 C7 112.61(15)
C10 C8 C7 109.50(17)
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
O1 C11 C8 112.36(14)
O1 C11 H11A 109.1
C8 C11 H11A 109.1
O1 C11 H11B 109.1
C8 C11 H11B 109.1
H11A C11 H11B 107.9
N2 C12 C13 120.96(16)
N2 C12 H12 119.5
C13 C12 H12 119.5
C18 C13 C14 117.55(19)
C18 C13 C12 119.94(17)
C14 C13 C12 122.49(18)
C15 C14 C13 120.5(2)
C15 C14 H14 119.7
C13 C14 H14 119.7
C16 C15 C14 120.4(2)
C16 C15 H15 119.8
C14 C15 H15 119.8
C17 C16 C15 119.8(2)
C17 C16 H16 120.1
C15 C16 H16 120.1
C16 C17 C18 120.2(2)
C16 C17 H17 119.9
C18 C17 H17 119.9
C13 C18 C17 121.5(2)
C13 C18 H18 119.3
C17 C18 H18 119.3
N2 N1 P1 118.82(12)
N2 N1 H1A 118.4(13)
P1 N1 H1A 122.7(13)
C12 N2 N1 116.99(15)
C11 O1 P1 120.09(12)
C7 O2 P1 121.54(10)
O3 P1 O1 115.05(7)
O3 P1 O2 115.21(7)
O1 P1 O2 104.12(6)
O3 P1 N1 110.68(8)
O1 P1 N1 105.92(8)
O2 P1 N1 104.92(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.387(4) no
C1 C6 1.391(3) no
C1 H1 0.9300 no
C2 C3 1.362(5) no
C2 H2 0.9300 no
C3 C4 1.358(5) no
C3 H3 0.9300 no
C4 C5 1.385(3) no
C4 H4 0.9300 no
C5 C6 1.378(3) no
C5 H5 0.9300 no
C6 C7 1.498(2) no
C7 O2 1.4639(19) yes
C7 C8 1.541(3) yes
C7 H7 0.9800 no
C8 C11 1.521(3) yes
C8 C9 1.521(3) yes
C8 C10 1.534(3) yes
C9 H9A 0.9600 no
C9 H9B 0.9600 no
C9 H9C 0.9600 no
C10 H10A 0.9600 no
C10 H10B 0.9600 no
C10 H10C 0.9600 no
C11 O1 1.453(2) yes
C11 H11A 0.9700 no
C11 H11B 0.9700 no
C12 N2 1.268(2) yes
C12 C13 1.463(2) no
C12 H12 0.9300 no
C13 C18 1.375(3) no
C13 C14 1.388(3) no
C14 C15 1.376(3) no
C14 H14 0.9300 no
C15 C16 1.371(4) no
C15 H15 0.9300 no
C16 C17 1.348(3) no
C16 H16 0.9300 no
C17 C18 1.377(3) no
C17 H17 0.9300 no
C18 H18 0.9300 no
N1 N2 1.390(2) yes
N1 P1 1.6230(16) yes
N1 H1A 0.853(8) no
O1 P1 1.5701(13) yes
O2 P1 1.5721(12) yes
O3 P1 1.4641(13) yes
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
C2 H2 O1 2_556 0.93 2.55 3.429(3) 158 yes
N1 H1A O3 3_667 0.853(8) 2.008(9) 2.856(2) 173.5(18) 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
C6 C1 C2 C3 -0.2(4)
C1 C2 C3 C4 0.7(5)
C2 C3 C4 C5 -0.6(5)
C3 C4 C5 C6 0.1(4)
C4 C5 C6 C1 0.4(3)
C4 C5 C6 C7 -176.3(2)
C2 C1 C6 C5 -0.3(3)
C2 C1 C6 C7 176.4(2)
C5 C6 C7 O2 33.9(2)
C1 C6 C7 O2 -142.77(18)
C5 C6 C7 C8 -88.8(2)
C1 C6 C7 C8 94.6(2)
O2 C7 C8 C11 59.63(18)
C6 C7 C8 C11 -179.52(16)
O2 C7 C8 C9 -61.95(19)
C6 C7 C8 C9 58.9(2)
O2 C7 C8 C10 174.92(15)
C6 C7 C8 C10 -64.2(2)
C9 C8 C11 O1 62.5(2)
C10 C8 C11 O1 -177.43(18)
C7 C8 C11 O1 -60.3(2)
N2 C12 C13 C18 -174.41(19)
N2 C12 C13 C14 4.3(3)
C18 C13 C14 C15 -0.3(4)
C12 C13 C14 C15 -179.1(2)
C13 C14 C15 C16 0.3(5)
C14 C15 C16 C17 0.1(5)
C15 C16 C17 C18 -0.5(4)
C14 C13 C18 C17 -0.1(3)
C12 C13 C18 C17 178.7(2)
C16 C17 C18 C13 0.5(4)
C13 C12 N2 N1 -178.97(17)
P1 N1 N2 C12 -176.25(15)
C8 C11 O1 P1 53.1(2)
C6 C7 O2 P1 177.71(12)
C8 C7 O2 P1 -54.46(17)
C11 O1 P1 O3 89.17(14)
C11 O1 P1 O2 -37.87(15)
C11 O1 P1 N1 -148.23(14)
C7 O2 P1 O3 -87.17(13)
C7 O2 P1 O1 39.77(14)
C7 O2 P1 N1 150.86(13)
N2 N1 P1 O3 -175.32(14)
N2 N1 P1 O1 59.35(16)
N2 N1 P1 O2 -50.45(16)
