#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:46:54 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180315 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/29/7152916.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7152916
loop_
_publ_author_name
'Fan, Weidong'
'Kong, Shasha'
'Cai, Yan'
'Wu, Guiping'
'Miao, Zhiwei'
_publ_section_title
;
 Diastereo- and enantioselective nitro-Mannich reaction of α-substituted
 nitroacetates to N-phosphoryl imines catalyzed by cinchona alkaloid
 thiourea organocatalysts.
;
_journal_issue                   19
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3223
_journal_page_last               3229
_journal_paper_doi               10.1039/c3ob40335a
_journal_volume                  11
_journal_year                    2013
_chemical_formula_sum            'C15 H23 N2 O7 P'
_chemical_formula_weight         374.32
_chemical_name_systematic
;
?
;
_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           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                   9.992(2)
_cell_length_b                   10.278(2)
_cell_length_c                   17.851(4)
_cell_measurement_reflns_used    6592
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.0
_cell_volume                     1833.3(7)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.22
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18945
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.9777
_exptl_absorpt_correction_T_min  0.9633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         4376
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0285
_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)+(0.0373P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0650
_refine_ls_wR_factor_ref         0.0668
_reflns_number_gt                3689
_reflns_number_total             4376
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob40335a.txt
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1833.4(7)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7152916
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.77874(3) 0.68615(3) 0.99435(2) 0.01626(8) Uani 1 1 d .
O1 O 0.65317(11) 1.07563(12) 0.84082(6) 0.0339(3) Uani 1 1 d .
O2 O 0.79834(13) 1.07120(15) 0.75185(7) 0.0541(4) Uani 1 1 d .
O3 O 0.93948(11) 0.76269(11) 0.79602(6) 0.0334(3) Uani 1 1 d .
O4 O 0.71743(11) 0.78778(10) 0.81292(6) 0.0268(2) Uani 1 1 d .
O5 O 0.63448(9) 0.71117(9) 0.99524(6) 0.0245(2) Uani 1 1 d .
O6 O 0.81135(9) 0.56841(9) 0.94120(5) 0.0197(2) Uani 1 1 d .
O7 O 0.84213(10) 0.63687(9) 1.06980(5) 0.0223(2) Uani 1 1 d .
N1 N 0.86269(11) 0.81516(11) 0.97000(6) 0.0157(2) Uani 1 1 d D
N2 N 0.76143(13) 1.04311(12) 0.81487(7) 0.0260(3) Uani 1 1 d .
C1 C 0.94819(14) 1.05713(15) 1.03671(8) 0.0231(3) Uani 1 1 d .
H1A H 1.0094 0.9864 1.0364 0.028 Uiso 1 1 calc R
C2 C 0.97436(15) 1.16549(15) 1.08061(8) 0.0264(3) Uani 1 1 d .
H2 H 1.0535 1.1682 1.1101 0.032 Uiso 1 1 calc R
C3 C 0.88687(16) 1.26952(15) 1.08205(8) 0.0271(3) Uani 1 1 d .
H3 H 0.9067 1.3445 1.1111 0.033 Uiso 1 1 calc R
C4 C 0.76994(16) 1.26313(14) 1.04068(8) 0.0277(3) Uani 1 1 d .
H4 H 0.7081 1.3333 1.0422 0.033 Uiso 1 1 calc R
C5 C 0.74256(14) 1.15448(13) 0.99684(8) 0.0220(3) Uani 1 1 d .
H5 H 0.6614 1.1507 0.9692 0.026 Uiso 1 1 calc R
C6 C 0.83250(13) 1.05112(12) 0.99283(8) 0.0163(3) Uani 1 1 d .
C7 C 0.80340(13) 0.93489(13) 0.94193(7) 0.0161(3) Uani 1 1 d .
H7 H 0.7042 0.9226 0.9398 0.019 Uiso 1 1 calc R
C8 C 0.85532(14) 0.95432(13) 0.85990(8) 0.0188(3) Uani 1 1 d .
C9 C 0.99573(15) 1.00946(16) 0.85444(8) 0.0273(4) Uani 1 1 d .
H9A H 1.0570 0.9558 0.8841 0.041 Uiso 1 1 calc R
H9B H 0.9963 1.0988 0.8737 0.041 Uiso 1 1 calc R
H9C H 1.0246 1.0094 0.8020 0.041 Uiso 1 1 calc R
C10 C 0.84574(15) 0.82309(15) 0.81873(8) 0.0220(3) Uani 1 1 d .
C11 C 0.69327(18) 0.66419(16) 0.77611(9) 0.0370(4) Uani 1 1 d .
H11A H 0.7464 0.6595 0.7300 0.056 Uiso 1 1 calc R
H11B H 0.5980 0.6566 0.7638 0.056 Uiso 1 1 calc R
H11C H 0.7191 0.5930 0.8097 0.056 Uiso 1 1 calc R
C12 C 0.94874(15) 0.52383(15) 0.93080(9) 0.0269(3) Uani 1 1 d .
H12A H 0.9864 0.4946 0.9792 0.032 Uiso 1 1 calc R
H12B H 1.0048 0.5959 0.9116 0.032 Uiso 1 1 calc R
C13 C 0.94815(18) 0.41298(17) 0.87576(9) 0.0360(4) Uani 1 1 d .
H13A H 0.8969 0.3401 0.8966 0.054 Uiso 1 1 calc R
H13B H 1.0403 0.3850 0.8661 0.054 Uiso 1 1 calc R
H13C H 0.9068 0.4416 0.8288 0.054 Uiso 1 1 calc R
C14 C 0.8468(2) 0.72518(16) 1.13381(9) 0.0361(4) Uani 1 1 d .
H14A H 0.7624 0.7754 1.1372 0.043 Uiso 1 1 calc R
H14B H 0.9219 0.7872 1.1281 0.043 Uiso 1 1 calc R
C15 C 0.86549(18) 0.64509(16) 1.20281(8) 0.0303(4) Uani 1 1 d .
H15A H 0.7882 0.5875 1.2094 0.045 Uiso 1 1 calc R
H15B H 0.8736 0.7025 1.2464 0.045 Uiso 1 1 calc R
H15C H 0.9469 0.5927 1.1979 0.045 Uiso 1 1 calc R
H1 H 0.9449(10) 0.8171(17) 0.9827(8) 0.031(5) Uiso 1 1 d D
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
O5 P1 O6 110.23(6)
O5 P1 O7 116.35(6)
O6 P1 O7 100.69(5)
O5 P1 N1 111.53(6)
O6 P1 N1 111.04(6)
O7 P1 N1 106.47(6)
C10 O4 C11 115.63(12)
C12 O6 P1 120.90(9)
C14 O7 P1 118.87(9)
C7 N1 P1 124.82(9)
C7 N1 H1 117.7(12)
P1 N1 H1 116.4(12)
O2 N2 O1 123.53(13)
O2 N2 C8 116.04(12)
O1 N2 C8 120.29(12)
C2 C1 C6 120.54(14)
C2 C1 H1A 119.7
C6 C1 H1A 119.7
C3 C2 C1 120.86(14)
C3 C2 H2 119.6
C1 C2 H2 119.6
C2 C3 C4 119.18(14)
C2 C3 H3 120.4
C4 C3 H3 120.4
C3 C4 C5 120.30(14)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C6 120.94(13)
C4 C5 H5 119.5
C6 C5 H5 119.5
C5 C6 C1 118.10(12)
C5 C6 C7 120.24(12)
C1 C6 C7 121.66(12)
N1 C7 C6 112.26(11)
N1 C7 C8 107.16(10)
C6 C7 C8 113.14(11)
N1 C7 H7 108.0
C6 C7 H7 108.0
C8 C7 H7 108.0
C9 C8 N2 108.02(12)
C9 C8 C10 110.76(12)
N2 C8 C10 103.46(10)
C9 C8 C7 114.48(12)
N2 C8 C7 111.26(11)
C10 C8 C7 108.31(11)
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
O3 C10 O4 125.79(15)
O3 C10 C8 124.66(14)
O4 C10 C8 109.55(12)
O4 C11 H11A 109.5
O4 C11 H11B 109.5
H11A C11 H11B 109.5
O4 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O6 C12 C13 108.50(12)
O6 C12 H12A 110.0
C13 C12 H12A 110.0
O6 C12 H12B 110.0
C13 C12 H12B 110.0
H12A C12 H12B 108.4
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
O7 C14 C15 107.86(13)
O7 C14 H14A 110.1
C15 C14 H14A 110.1
O7 C14 H14B 110.1
C15 C14 H14B 110.1
H14A C14 H14B 108.4
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O5 1.4644(10)
P1 O6 1.5720(10)
P1 O7 1.5722(11)
P1 N1 1.6281(12)
O1 N2 1.2233(15)
O2 N2 1.2187(17)
O3 C10 1.1946(17)
O4 C10 1.3365(18)
O4 C11 1.4504(18)
O6 C12 1.4591(17)
O7 C14 1.4600(17)
N1 C7 1.4548(17)
N1 H1 0.852(9)
N2 C8 1.5360(18)
C1 C2 1.387(2)
C1 C6 1.3977(19)
C1 H1A 0.9500
C2 C3 1.381(2)
C2 H2 0.9500
C3 C4 1.384(2)
C3 H3 0.9500
C4 C5 1.391(2)
C4 H4 0.9500
C5 C6 1.3933(18)
C5 H5 0.9500
C6 C7 1.5289(18)
C7 C8 1.5662(19)
C7 H7 1.0000
C8 C9 1.516(2)
C8 C10 1.539(2)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C13 1.505(2)
C12 H12A 0.9900
C12 H12B 0.9900
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 C15 1.493(2)
C14 H14A 0.9900
C14 H14B 0.9900
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O5 0.852(9) 1.957(10) 2.7988(16) 169.4(17) 4_567
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
O5 P1 O6 C12 -179.84(10)
O7 P1 O6 C12 -56.41(11)
N1 P1 O6 C12 56.04(12)
O5 P1 O7 C14 -67.46(13)
O6 P1 O7 C14 173.45(11)
N1 P1 O7 C14 57.55(13)
O5 P1 N1 C7 -8.46(13)
O6 P1 N1 C7 114.91(10)
O7 P1 N1 C7 -136.36(10)
C6 C1 C2 C3 0.1(2)
C1 C2 C3 C4 1.9(2)
C2 C3 C4 C5 -1.5(2)
C3 C4 C5 C6 -0.9(2)
C4 C5 C6 C1 2.8(2)
C4 C5 C6 C7 -177.55(13)
C2 C1 C6 C5 -2.4(2)
C2 C1 C6 C7 177.94(13)
P1 N1 C7 C6 118.23(11)
P1 N1 C7 C8 -116.96(11)
C5 C6 C7 N1 -150.98(12)
C1 C6 C7 N1 28.66(17)
C5 C6 C7 C8 87.58(15)
C1 C6 C7 C8 -92.78(15)
O2 N2 C8 C9 48.71(17)
O1 N2 C8 C9 -135.38(14)
O2 N2 C8 C10 -68.75(17)
O1 N2 C8 C10 107.16(14)
O2 N2 C8 C7 175.16(14)
O1 N2 C8 C7 -8.93(18)
N1 C7 C8 C9 -79.36(14)
C6 C7 C8 C9 44.91(16)
N1 C7 C8 N2 157.83(11)
C6 C7 C8 N2 -77.90(13)
N1 C7 C8 C10 44.76(14)
C6 C7 C8 C10 169.03(11)
C11 O4 C10 O3 0.6(2)
C11 O4 C10 C8 -179.09(11)
C9 C8 C10 O3 11.14(19)
N2 C8 C10 O3 126.67(15)
C7 C8 C10 O3 -115.17(16)
C9 C8 C10 O4 -169.18(12)
N2 C8 C10 O4 -53.66(14)
C7 C8 C10 O4 64.51(13)
P1 O6 C12 C13 -178.59(10)
P1 O7 C14 C15 160.70(11)
