#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:45:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180314 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/28/7152824.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_7152824
loop_
_publ_author_name
'Arróniz, Carlos'
'Molina, Juan'
'Abás, Sonia'
'Molins, Elies'
'Campanera, Josep M.'
'Luque, F. Javier'
'Escolano, Carmen'
_publ_section_title
;
 First diastereoselective [3 + 2] cycloaddition reaction of diethyl
 isocyanomethylphosphonate and maleimides.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1640
_journal_page_last               1649
_journal_paper_doi               10.1039/c3ob26766k
_journal_volume                  11
_journal_year                    2013
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H19 N2 O5 P1'
_chemical_formula_sum            'C16 H19 N2 O5 P'
_chemical_formula_weight         350.3
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-02-27T17:03:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                111.01(7)
_cell_angle_beta                 92.49(7)
_cell_angle_gamma                101.66(8)
_cell_formula_units_Z            2
_cell_length_a                   6.116(6)
_cell_length_b                   11.264(7)
_cell_length_c                   13.284(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      3
_cell_measurement_wavelength     0.71073
_cell_volume                     829.9(12)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_orient_matrix_type
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.007368
_diffrn_orient_matrix_UB_12      -0.001921
_diffrn_orient_matrix_UB_13      -0.075917
_diffrn_orient_matrix_UB_21      -0.01403
_diffrn_orient_matrix_UB_22      0.092892
_diffrn_orient_matrix_UB_23      0.027542
_diffrn_orient_matrix_UB_31      0.167495
_diffrn_orient_matrix_UB_32      0.030487
_diffrn_orient_matrix_UB_33      0.009508
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1558
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2918
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         1.66
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_correction_T_min  0.8895
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.23
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.898
_refine_ls_R_factor_all          0.1876
_refine_ls_R_factor_gt           0.0659
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0676P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1696
_reflns_number_gt                1204
_reflns_number_total             2918
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob26766k.txt
_cod_data_source_block           jb93
_cod_database_code               7152824
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 -0.1021(3) 0.38829(16) 0.63258(13) 0.0565(5) Uani 1 1 d .
O1 O -0.2033(6) 0.4536(4) 0.5726(3) 0.0624(11) Uani 1 1 d .
O2 O 0.1266(6) 0.4657(4) 0.7066(3) 0.0749(12) Uani 1 1 d .
O3 O -0.2592(6) 0.3546(4) 0.7124(3) 0.0713(12) Uani 1 1 d .
O6 O 0.4413(6) 0.0193(4) 0.3577(3) 0.0676(11) Uani 1 1 d .
O8 O -0.1588(7) 0.1739(4) 0.2874(3) 0.0730(12) Uani 1 1 d .
N1 N 0.0526(8) 0.1700(4) 0.6003(4) 0.0604(13) Uani 1 1 d .
N7 N 0.1329(7) 0.0770(4) 0.2975(4) 0.0527(11) Uani 1 1 d .
C2 C 0.2396(10) 0.1541(5) 0.5661(5) 0.0628(16) Uani 1 1 d .
H2 H 0.332 0.1149 0.5949 0.075 Uiso 1 1 calc R
C3 C 0.3039(8) 0.2014(5) 0.4774(4) 0.0526(14) Uani 1 1 d .
H3 H 0.4447 0.269 0.4987 0.063 Uiso 1 1 calc R
C4 C 0.1008(8) 0.2524(5) 0.4550(4) 0.0497(14) Uani 1 1 d .
H4 H 0.1462 0.3444 0.4635 0.06 Uiso 1 1 calc R
C5 C -0.0547(9) 0.2353(5) 0.5413(4) 0.0552(15) Uani 1 1 d .
H5 H -0.2002 0.1778 0.5033 0.066 Uiso 1 1 calc R
C6 C 0.3076(8) 0.0875(5) 0.3736(4) 0.0510(14) Uani 1 1 d .
C8 C 0.0006(9) 0.1652(5) 0.3378(5) 0.0566(15) Uani 1 1 d .
C21 C 0.3107(11) 0.5402(7) 0.6771(5) 0.088(2) Uani 1 1 d .
H21A H 0.2537 0.5855 0.6357 0.106 Uiso 1 1 calc R
H21B H 0.3934 0.4816 0.6308 0.106 Uiso 1 1 calc R
C22 C 0.4609(11) 0.6342(6) 0.7701(5) 0.091(2) Uani 1 1 d .
H22A H 0.3796 0.692 0.8165 0.136 Uiso 1 1 calc R
H22B H 0.58 0.6838 0.7466 0.136 Uiso 1 1 calc R
H22C H 0.5235 0.5895 0.8094 0.136 Uiso 1 1 calc R
C31 C -0.1996(12) 0.3256(7) 0.8054(5) 0.093(2) Uani 1 1 d .
H31A H -0.0371 0.3486 0.823 0.112 Uiso 1 1 calc R
H31B H -0.2519 0.2326 0.7888 0.112 Uiso 1 1 calc R
C32 C -0.2996(16) 0.3982(9) 0.8979(6) 0.149(4) Uani 1 1 d .
H32A H -0.4557 0.3893 0.876 0.223 Uiso 1 1 calc R
H32B H -0.2229 0.4889 0.9245 0.223 Uiso 1 1 calc R
H32C H -0.2865 0.3646 0.9543 0.223 Uiso 1 1 calc R
C71 C 0.0917(9) -0.0174(6) 0.1877(4) 0.0550(14) Uani 1 1 d .
C72 C 0.2620(10) -0.0227(6) 0.1237(5) 0.0683(17) Uani 1 1 d .
H72 H 0.4038 0.0323 0.1519 0.082 Uiso 1 1 calc R
C73 C 0.2222(12) -0.1097(7) 0.0178(5) 0.082(2) Uani 1 1 d .
H73 H 0.3378 -0.1143 -0.0257 0.098 Uiso 1 1 calc R
C74 C 0.0122(13) -0.1899(7) -0.0242(5) 0.082(2) Uani 1 1 d .
H74 H -0.0139 -0.2478 -0.0963 0.099 Uiso 1 1 calc R
C75 C -0.1612(11) -0.1855(6) 0.0397(5) 0.0781(19) Uani 1 1 d .
H75 H -0.3029 -0.2405 0.011 0.094 Uiso 1 1 calc R
C76 C -0.1212(10) -0.0973(6) 0.1482(5) 0.0653(17) Uani 1 1 d .
H76 H -0.2353 -0.0926 0.1925 0.078 Uiso 1 1 calc R
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'
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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 0 0
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 P1 O3 111.4(2)
O1 P1 O2 117.2(2)
O3 P1 O2 103.7(2)
O1 P1 C5 110.9(3)
O3 P1 C5 106.5(3)
O2 P1 C5 106.5(3)
C21 O2 P1 125.4(4)
C31 O3 P1 128.0(4)
C2 N1 C5 109.6(5)
C8 N7 C6 113.6(5)
C8 N7 C71 122.8(4)
C6 N7 C71 123.5(4)
N1 C2 C3 116.9(5)
C2 C3 C6 110.6(5)
C2 C3 C4 102.5(4)
C6 C3 C4 105.2(4)
C3 C4 C8 105.1(4)
C3 C4 C5 104.2(4)
C8 C4 C5 113.8(4)
N1 C5 C4 106.7(4)
N1 C5 P1 111.5(4)
C4 C5 P1 112.8(4)
O6 C6 N7 125.4(5)
O6 C6 C3 126.4(5)
N7 C6 C3 108.2(4)
O8 C8 N7 125.4(5)
O8 C8 C4 126.7(5)
N7 C8 C4 107.8(5)
O2 C21 C22 112.3(6)
O3 C31 C32 110.3(6)
C72 C71 C76 121.6(6)
C72 C71 N7 119.3(5)
C76 C71 N7 119.1(5)
C71 C72 C73 119.7(6)
C74 C73 C72 120.2(6)
C73 C74 C75 120.7(6)
C74 C75 C76 119.4(6)
C71 C76 C75 118.5(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.455(4)
P1 O3 1.556(4)
P1 O2 1.567(4)
P1 C5 1.805(6)
O2 C21 1.421(7)
O3 C31 1.437(7)
O6 C6 1.206(6)
O8 C8 1.198(6)
N1 C2 1.271(7)
N1 C5 1.465(7)
N7 C8 1.382(6)
N7 C6 1.395(6)
N7 C71 1.438(7)
C2 C3 1.494(7)
C3 C6 1.514(7)
C3 C4 1.529(7)
C4 C8 1.531(8)
C4 C5 1.561(7)
C21 C22 1.436(8)
C31 C32 1.448(8)
C71 C72 1.370(7)
C71 C76 1.381(7)
C72 C73 1.373(8)
C73 C74 1.372(8)
C74 C75 1.385(8)
C75 C76 1.403(8)
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
O1 P1 O2 C21 -43.5(6)
O3 P1 O2 C21 -166.7(5)
C5 P1 O2 C21 81.2(5)
O1 P1 O3 C31 -160.7(5)
O2 P1 O3 C31 -33.8(6)
C5 P1 O3 C31 78.4(6)
C5 N1 C2 C3 -0.7(7)
N1 C2 C3 C6 -113.6(6)
N1 C2 C3 C4 -1.9(6)
C2 C3 C4 C8 -116.6(4)
C6 C3 C4 C8 -0.9(6)
C2 C3 C4 C5 3.4(5)
C6 C3 C4 C5 119.1(4)
C2 N1 C5 C4 2.9(6)
C2 N1 C5 P1 -120.7(5)
C3 C4 C5 N1 -3.9(5)
C8 C4 C5 N1 110.0(5)
C3 C4 C5 P1 118.8(4)
C8 C4 C5 P1 -127.3(4)
O1 P1 C5 N1 178.5(3)
O3 P1 C5 N1 -60.2(4)
O2 P1 C5 N1 50.0(4)
O1 P1 C5 C4 58.5(4)
O3 P1 C5 C4 179.8(4)
O2 P1 C5 C4 -70.0(4)
C8 N7 C6 O6 178.4(5)
C71 N7 C6 O6 -0.9(8)
C8 N7 C6 C3 -3.4(6)
C71 N7 C6 C3 177.2(5)
C2 C3 C6 O6 -69.4(7)
C4 C3 C6 O6 -179.3(5)
C2 C3 C6 N7 112.5(5)
C4 C3 C6 N7 2.5(6)
C6 N7 C8 O8 -179.8(5)
C71 N7 C8 O8 -0.4(9)
C6 N7 C8 C4 2.8(6)
C71 N7 C8 C4 -177.8(4)
C3 C4 C8 O8 -178.4(6)
C5 C4 C8 O8 68.2(7)
C3 C4 C8 N7 -1.0(6)
C5 C4 C8 N7 -114.4(5)
P1 O2 C21 C22 159.8(5)
P1 O3 C31 C32 133.5(6)
C8 N7 C71 C72 125.9(6)
C6 N7 C71 C72 -54.8(7)
C8 N7 C71 C76 -51.8(7)
C6 N7 C71 C76 127.5(6)
C76 C71 C72 C73 -0.3(9)
N7 C71 C72 C73 -178.0(5)
C71 C72 C73 C74 0.7(10)
C72 C73 C74 C75 -0.8(10)
C73 C74 C75 C76 0.4(10)
C72 C71 C76 C75 0.0(9)
N7 C71 C76 C75 177.7(5)
C74 C75 C76 C71 -0.1(9)
