#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:47:24 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178444 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/65/4026591.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_4026591
loop_
_publ_author_name
'Silong Xu'
'Rongshun Chen'
'Zhengjie He'
_publ_section_title
;
 PBu3-Mediated Vinylogous Wittig Reaction of α-Methyl Allenoates with
 Aldehydes and Mechanistic Investigations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7528
_journal_page_last               7538
_journal_paper_doi               10.1021/jo201466k
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C15 H17 N O5'
_chemical_formula_sum            'C15 H17 N O5'
_chemical_formula_weight         291.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 102.794(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.261(4)
_cell_length_b                   7.7830(10)
_cell_length_c                   13.361(2)
_cell_measurement_reflns_used    5068
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      1.60
_cell_volume                     2865.9(7)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17703
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         1.48
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_correction_T_min  0.9779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       prism
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0387
_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)+(0.0724P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1095
_reflns_number_gt                2476
_reflns_number_total             3416
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201466k_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4026591
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.03675(3) -0.32274(10) -0.01435(6) 0.0276(2) Uani 1 1 d .
O2 O 0.11072(4) -0.40702(11) 0.16994(6) 0.0372(2) Uani 1 1 d .
O3 O 0.05538(3) -0.29578(12) 0.23911(6) 0.0348(2) Uani 1 1 d .
O4 O 0.19616(3) -0.10614(10) 0.43342(6) 0.0302(2) Uani 1 1 d .
O5 O 0.20854(3) 0.05504(10) 0.57512(6) 0.0247(2) Uani 1 1 d .
N1 N 0.08218(3) -0.29220(12) 0.17880(7) 0.0234(2) Uani 1 1 d .
C1 C 0.05498(4) -0.16281(14) 0.01025(8) 0.0205(2) Uani 1 1 d .
C2 C 0.07964(4) -0.14050(14) 0.11202(8) 0.0187(2) Uani 1 1 d .
C3 C 0.10054(4) 0.01340(14) 0.15271(8) 0.0190(2) Uani 1 1 d .
C4 C 0.09574(4) 0.15177(15) 0.08409(8) 0.0227(2) Uani 1 1 d .
H4 H 0.1096 0.2597 0.1074 0.027 Uiso 1 1 calc R
C5 C 0.07114(4) 0.13350(15) -0.01683(8) 0.0250(3) Uani 1 1 d .
H5 H 0.0682 0.2298 -0.0615 0.030 Uiso 1 1 calc R
C6 C 0.05060(4) -0.02242(15) -0.05483(8) 0.0236(3) Uani 1 1 d .
H6 H 0.0338 -0.0324 -0.1245 0.028 Uiso 1 1 calc R
C7 C 0.01527(4) -0.35528(18) -0.12010(8) 0.0308(3) Uani 1 1 d .
H7A H -0.0133 -0.2816 -0.1421 0.037 Uiso 1 1 calc R
H7B H 0.0054 -0.4761 -0.1287 0.037 Uiso 1 1 calc R
H7C H 0.0389 -0.3305 -0.1618 0.037 Uiso 1 1 calc R
C8 C 0.12708(4) 0.02193(14) 0.26016(8) 0.0202(2) Uani 1 1 d .
H8 H 0.1360 -0.0838 0.2948 0.024 Uiso 1 1 calc R
C9 C 0.13974(4) 0.16740(14) 0.31358(8) 0.0196(2) Uani 1 1 d .
H9 H 0.1304 0.2718 0.2778 0.024 Uiso 1 1 calc R
C10 C 0.16632(4) 0.18382(13) 0.42044(8) 0.0191(2) Uani 1 1 d .
C11 C 0.16902(4) 0.33225(14) 0.47283(8) 0.0233(2) Uani 1 1 d .
H11 H 0.1884 0.3306 0.5407 0.028 Uiso 1 1 calc R
C12 C 0.14531(5) 0.49904(15) 0.43716(9) 0.0295(3) Uani 1 1 d .
H12A H 0.1333 0.4959 0.3625 0.035 Uiso 1 1 calc R
H12B H 0.1689 0.5924 0.4553 0.035 Uiso 1 1 calc R
H12C H 0.1181 0.5186 0.4702 0.035 Uiso 1 1 calc R
C13 C 0.19132(4) 0.02952(14) 0.47429(8) 0.0200(2) Uani 1 1 d .
C14 C 0.23293(4) -0.09105(15) 0.63199(8) 0.0269(3) Uani 1 1 d .
H14A H 0.2557 -0.1437 0.5944 0.032 Uiso 1 1 calc R
H14B H 0.2089 -0.1789 0.6410 0.032 Uiso 1 1 calc R
C15 C 0.26005(4) -0.02626(17) 0.73484(9) 0.0308(3) Uani 1 1 d .
H15A H 0.2834 0.0617 0.7250 0.037 Uiso 1 1 calc R
H15B H 0.2774 -0.1218 0.7746 0.037 Uiso 1 1 calc R
H15C H 0.2370 0.0235 0.7719 0.037 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
C1 O1 C7 117.12(9)
C13 O5 C14 115.69(8)
O3 N1 O2 124.31(10)
O3 N1 C2 117.63(9)
O2 N1 C2 118.06(9)
O1 C1 C6 126.46(10)
O1 C1 C2 115.51(9)
C6 C1 C2 118.02(10)
C3 C2 C1 124.42(10)
C3 C2 N1 119.60(9)
C1 C2 N1 115.96(9)
C2 C3 C4 115.76(9)
C2 C3 C8 120.14(9)
C4 C3 C8 124.06(10)
C5 C4 C3 120.98(10)
C5 C4 H4 119.5
C3 C4 H4 119.5
C4 C5 C6 121.68(10)
C4 C5 H5 119.2
C6 C5 H5 119.2
C1 C6 C5 119.13(10)
C1 C6 H6 120.4
C5 C6 H6 120.4
O1 C7 H7A 109.5
O1 C7 H7B 109.5
H7A C7 H7B 109.5
O1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 C3 125.19(10)
C9 C8 H8 117.4
C3 C8 H8 117.4
C8 C9 C10 127.60(10)
C8 C9 H9 116.2
C10 C9 H9 116.2
C11 C10 C9 122.72(10)
C11 C10 C13 118.27(10)
C9 C10 C13 119.01(9)
C10 C11 C12 127.78(10)
C10 C11 H11 116.1
C12 C11 H11 116.1
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
O4 C13 O5 122.01(10)
O4 C13 C10 124.91(10)
O5 C13 C10 113.08(9)
O5 C14 C15 107.57(9)
O5 C14 H14A 110.2
C15 C14 H14A 110.2
O5 C14 H14B 110.2
C15 C14 H14B 110.2
H14A C14 H14B 108.5
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 C1 1.3593(13)
O1 C7 1.4315(13)
O2 N1 1.2271(12)
O3 N1 1.2222(12)
O4 C13 1.2103(13)
O5 C13 1.3419(13)
O5 C14 1.4538(13)
N1 C2 1.4721(14)
C1 C6 1.3848(15)
C1 C2 1.3946(14)
C2 C3 1.3917(15)
C3 C4 1.4013(15)
C3 C8 1.4666(14)
C4 C5 1.3807(15)
C4 H4 0.9500
C5 C6 1.3918(16)
C5 H5 0.9500
C6 H6 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 C9 1.3440(15)
C8 H8 0.9500
C9 C10 1.4642(15)
C9 H9 0.9500
C10 C11 1.3441(14)
C10 C13 1.4946(15)
C11 C12 1.4899(16)
C11 H11 0.9500
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C14 C15 1.5045(16)
C14 H14A 0.9900
C14 H14B 0.9900
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
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
C7 O1 C1 C6 7.00(16)
C7 O1 C1 C2 -174.20(9)
O1 C1 C2 C3 -179.38(9)
C6 C1 C2 C3 -0.47(16)
O1 C1 C2 N1 -0.51(14)
C6 C1 C2 N1 178.41(9)
O3 N1 C2 C3 75.28(13)
O2 N1 C2 C3 -105.18(12)
O3 N1 C2 C1 -103.66(11)
O2 N1 C2 C1 75.89(13)
C1 C2 C3 C4 -0.17(16)
N1 C2 C3 C4 -179.01(9)
C1 C2 C3 C8 -178.05(9)
N1 C2 C3 C8 3.11(15)
C2 C3 C4 C5 0.72(15)
C8 C3 C4 C5 178.50(10)
C3 C4 C5 C6 -0.63(17)
O1 C1 C6 C5 179.35(10)
C2 C1 C6 C5 0.57(16)
C4 C5 C6 C1 -0.04(16)
C2 C3 C8 C9 -165.17(10)
C4 C3 C8 C9 17.14(17)
C3 C8 C9 C10 -179.71(9)
C8 C9 C10 C11 -166.64(11)
C8 C9 C10 C13 12.96(16)
C9 C10 C11 C12 2.74(18)
C13 C10 C11 C12 -176.86(10)
C14 O5 C13 O4 -0.54(15)
C14 O5 C13 C10 179.51(9)
C11 C10 C13 O4 -171.68(11)
C9 C10 C13 O4 8.70(16)
C11 C10 C13 O5 8.27(14)
C9 C10 C13 O5 -171.35(9)
C13 O5 C14 C15 166.06(9)
