#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/33/1503395.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_1503395
loop_
_publ_author_name
'Xu, Silong'
'Zhou, Lili'
'Ma, Renqin'
'Song, Haibin'
'He, Zhengjie'
_publ_section_title
;
 Phosphine-mediated stereoselective reductive cyclopropanation of
 alpha-substituted allenoates with aromatic aldehydes.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              544
_journal_page_last               547
_journal_paper_doi               10.1021/ol902747c
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C15 H14 N2 O4'
_chemical_formula_weight         286.28
_chemical_name_systematic
; 
 ? 
;
_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                 90.14(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.852(2)
_cell_length_b                   12.744(3)
_cell_length_c                   10.025(2)
_cell_measurement_reflns_used    2807
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.876
_cell_measurement_theta_min      1.817
_cell_volume                     1386.4(5)
_computing_cell_refinement       crystalclear
_computing_data_collection       'crystalclear(Rigaku/MSC Inc., 2005)'
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'rigaku saturn CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6764
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_correction_T_min  0.9801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.023(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.180
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0575
_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)+(0.1069P)²+0.2082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1859
_refine_ls_wR_factor_ref         0.1955
_reflns_number_gt                1982
_reflns_number_total             2429
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902747c_si_003.cif
_cod_data_source_block           r90630b1
_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 2.4.2 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.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' 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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1503395
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_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
O1 O 0.63777(17) 0.37268(15) 0.0250(2) 0.0329(6) Uani 1 1 d .
O2 O 0.65070(17) 0.24148(15) -0.1113(2) 0.0309(5) Uani 1 1 d .
O3 O 0.11501(16) 0.07461(14) 0.17360(19) 0.0287(5) Uani 1 1 d .
O4 O -0.05869(18) -0.01187(15) 0.2255(2) 0.0361(6) Uani 1 1 d .
N1 N 0.5899(2) 0.30444(17) -0.0451(2) 0.0258(6) Uani 1 1 d .
N2 N -0.3548(2) 0.03660(19) 0.2127(3) 0.0325(6) Uani 1 1 d .
C1 C 0.2598(2) 0.3583(2) 0.0251(3) 0.0231(6) Uani 1 1 d .
H1 H 0.2121 0.4067 0.0713 0.028 Uiso 1 1 calc R
C2 C 0.3870(2) 0.3691(2) 0.0236(3) 0.0233(6) Uani 1 1 d .
H2 H 0.4253 0.4237 0.0691 0.028 Uiso 1 1 calc R
C3 C 0.4554(2) 0.2965(2) -0.0473(3) 0.0216(6) Uani 1 1 d .
C4 C 0.4020(2) 0.2148(2) -0.1176(3) 0.0244(6) Uani 1 1 d .
H4 H 0.4500 0.1677 -0.1656 0.029 Uiso 1 1 calc R
C5 C 0.2750(2) 0.2051(2) -0.1144(3) 0.0253(6) Uani 1 1 d .
H5 H 0.2373 0.1508 -0.1612 0.030 Uiso 1 1 calc R
C6 C 0.2025(2) 0.2753(2) -0.0420(3) 0.0214(6) Uani 1 1 d .
C7 C 0.0682(2) 0.2543(2) -0.0312(2) 0.0220(6) Uani 1 1 d .
H7 H 0.0372 0.1992 -0.0906 0.026 Uiso 1 1 calc R
C8 C -0.0265(2) 0.3361(2) 0.0083(3) 0.0261(7) Uani 1 1 d .
H8A H 0.0022 0.4073 0.0225 0.031 Uiso 1 1 calc R
H8B H -0.1082 0.3305 -0.0303 0.031 Uiso 1 1 calc R
C9 C 0.0111(2) 0.2551(2) 0.1072(3) 0.0217(6) Uani 1 1 d .
H9 H 0.0659 0.2808 0.1779 0.026 Uiso 1 1 calc R
C10 C -0.0690(2) 0.1664(2) 0.1474(2) 0.0212(6) Uani 1 1 d .
C11 C -0.1919(2) 0.1750(2) 0.1498(3) 0.0227(6) Uani 1 1 d .
H11 H -0.2248 0.2397 0.1258 0.027 Uiso 1 1 calc R
C12 C -0.2777(2) 0.0943(2) 0.1856(3) 0.0257(7) Uani 1 1 d .
C13 C -0.0068(2) 0.0660(2) 0.1870(3) 0.0235(6) Uani 1 1 d .
C14 C 0.1901(2) -0.0149(2) 0.2134(3) 0.0309(7) Uani 1 1 d .
H14A H 0.1665 -0.0769 0.1634 0.037 Uiso 1 1 calc R
H14B H 0.1798 -0.0292 0.3077 0.037 Uiso 1 1 calc R
C15 C 0.3218(2) 0.0140(2) 0.1841(3) 0.0308(7) Uani 1 1 d .
H15A H 0.3319 0.0230 0.0897 0.046 Uiso 1 1 calc R
H15B H 0.3753 -0.0409 0.2150 0.046 Uiso 1 1 calc R
H15C H 0.3420 0.0783 0.2289 0.046 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 0.0000 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C13 O3 C14 117.5(2)
O1 N1 O2 122.8(2)
O1 N1 C3 118.5(2)
O2 N1 C3 118.8(2)
C2 C1 C6 120.7(2)
C2 C1 H1 119.6
C6 C1 H1 119.6
C3 C2 C1 118.3(2)
C3 C2 H2 120.9
C1 C2 H2 120.9
C4 C3 C2 122.7(2)
C4 C3 N1 118.5(2)
C2 C3 N1 118.8(2)
C5 C4 C3 118.1(2)
C5 C4 H4 120.9
C3 C4 H4 120.9
C4 C5 C6 121.2(2)
C4 C5 H5 119.4
C6 C5 H5 119.4
C5 C6 C1 119.0(2)
C5 C6 C7 118.5(2)
C1 C6 C7 122.4(2)
C6 C7 C8 124.1(2)
C6 C7 C9 117.9(2)
C8 C7 C9 58.63(17)
C6 C7 H7 114.8
C8 C7 H7 114.8
C9 C7 H7 114.8
C9 C8 C7 60.81(17)
C9 C8 H8A 117.7
C7 C8 H8A 117.7
C9 C8 H8B 117.7
C7 C8 H8B 117.7
H8A C8 H8B 114.8
C10 C9 C8 123.4(2)
C10 C9 C7 118.9(2)
C8 C9 C7 60.56(17)
C10 C9 H9 114.4
C8 C9 H9 114.4
C7 C9 H9 114.4
C11 C10 C9 121.8(2)
C11 C10 C13 120.9(2)
C9 C10 C13 117.3(2)
C10 C11 C12 126.4(2)
C10 C11 H11 116.8
C12 C11 H11 116.8
N2 C12 C11 173.6(3)
O4 C13 O3 124.3(2)
O4 C13 C10 125.3(2)
O3 C13 C10 110.4(2)
O3 C14 C15 106.6(2)
O3 C14 H14A 110.4
C15 C14 H14A 110.4
O3 C14 H14B 110.4
C15 C14 H14B 110.4
H14A C14 H14B 108.6
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
O1 N1 1.232(3)
O2 N1 1.233(3)
O3 C13 1.334(3)
O3 C14 1.457(3)
O4 C13 1.205(3)
N1 C3 1.464(3)
N2 C12 1.147(3)
C1 C2 1.387(4)
C1 C6 1.399(4)
C1 H1 0.9300
C2 C3 1.385(4)
C2 H2 0.9300
C3 C4 1.384(4)
C4 C5 1.383(4)
C4 H4 0.9300
C5 C6 1.396(4)
C5 H5 0.9300
C6 C7 1.486(3)
C7 C8 1.517(4)
C7 C9 1.521(4)
C7 H7 0.9800
C8 C9 1.488(4)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.482(4)
C9 H9 0.9800
C10 C11 1.338(4)
C10 C13 1.499(4)
C11 C12 1.434(4)
C11 H11 0.9300
C14 C15 1.505(4)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
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 0.8(4)
C1 C2 C3 C4 0.8(4)
C1 C2 C3 N1 -177.5(2)
O1 N1 C3 C4 -175.0(2)
O2 N1 C3 C4 3.7(4)
O1 N1 C3 C2 3.3(3)
O2 N1 C3 C2 -178.0(2)
C2 C3 C4 C5 -1.0(4)
N1 C3 C4 C5 177.2(2)
C3 C4 C5 C6 -0.2(4)
C4 C5 C6 C1 1.7(4)
C4 C5 C6 C7 -173.8(2)
C2 C1 C6 C5 -2.0(4)
C2 C1 C6 C7 173.4(2)
C5 C6 C7 C8 -161.9(3)
C1 C6 C7 C8 22.7(4)
C5 C6 C7 C9 128.8(3)
C1 C6 C7 C9 -46.6(3)
C6 C7 C8 C9 -104.4(3)
C7 C8 C9 C10 -107.0(3)
C6 C7 C9 C10 -131.0(2)
C8 C7 C9 C10 114.2(3)
C6 C7 C9 C8 114.8(3)
C8 C9 C10 C11 -31.2(4)
C7 C9 C10 C11 -103.2(3)
C8 C9 C10 C13 149.4(2)
C7 C9 C10 C13 77.3(3)
C9 C10 C11 C12 179.3(2)
C13 C10 C11 C12 -1.2(4)
C10 C11 C12 N2 177(2)
C14 O3 C13 O4 -2.5(4)
C14 O3 C13 C10 177.4(2)
C11 C10 C13 O4 -1.7(4)
C9 C10 C13 O4 177.8(3)
C11 C10 C13 O3 178.4(2)
C9 C10 C13 O3 -2.2(3)
C13 O3 C14 C15 178.2(2)
