#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:26:39 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178812 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/66/4106651.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_4106651
loop_
_publ_author_name
'Risong Na'
'Chengfeng Jing'
'Qihai Xu'
'Hui Jiang'
'Xi Wu'
'Jiayan Shi'
'Jiangchun Zhong'
'Min Wang'
'Diego Benitez'
'Ekaterina Tkatchouk'
'William A. Goddard'
'Hongchao Guo'
'Ohyun Kwon'
_publ_section_title
;
 Phosphine-Catalyzed Annulations of Azomethine Imines: Allene-Dependent [3
 + 2], [3 + 3], [4 + 3], and [3 + 2 + 3] Pathways
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13337
_journal_page_last               13348
_journal_paper_doi               10.1021/ja200231v
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C20 H23 N3 O7'
_chemical_formula_sum            'C20 H23 N3 O7'
_chemical_formula_weight         417.41
_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                 107.406(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.759(2)
_cell_length_b                   23.045(4)
_cell_length_c                   7.7057(14)
_cell_measurement_reflns_used    6066
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.98
_cell_measurement_theta_min      3.84
_cell_volume                     1992.5(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            27165
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         30.76
_diffrn_reflns_theta_min         3.74
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_correction_T_min  0.9378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Bruker)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0592P)²+0.4470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1219
_reflns_number_gt                4460
_reflns_number_total             5876
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja200231v_si_005.cif
_cod_data_source_block           kw210sa
_cod_original_cell_volume        1992.6(6)
_cod_database_code               4106651
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 0.58175(9) 0.14506(4) 0.57466(15) 0.0312(2) Uani 1 1 d .
O2 O 0.72307(9) 0.18685(4) 0.49505(16) 0.0355(3) Uani 1 1 d .
O3 O 0.16915(9) 0.54083(4) 0.63533(14) 0.0294(2) Uani 1 1 d .
O4 O 0.35800(8) 0.51798(4) 0.31671(14) 0.0265(2) Uani 1 1 d .
O5 O 0.18580(8) 0.48983(4) 0.11530(13) 0.0235(2) Uani 1 1 d .
O6 O 0.23618(9) 0.34289(4) -0.01503(14) 0.0276(2) Uani 1 1 d .
O7 O 0.07955(8) 0.30657(4) 0.05813(12) 0.01994(19) Uani 1 1 d .
N1 N 0.62905(10) 0.18823(4) 0.53335(15) 0.0228(2) Uani 1 1 d .
N2 N 0.32236(9) 0.41089(4) 0.62401(14) 0.0189(2) Uani 1 1 d .
N3 N 0.22539(9) 0.45084(4) 0.56379(14) 0.0194(2) Uani 1 1 d .
C1 C 0.56941(11) 0.24474(5) 0.52912(17) 0.0197(2) Uani 1 1 d .
C2 C 0.45710(12) 0.24576(5) 0.55033(19) 0.0238(3) Uani 1 1 d .
H2 H 0.4195 0.2109 0.5702 0.029 Uiso 1 1 calc R
C3 C 0.40029(11) 0.29893(5) 0.54198(19) 0.0234(3) Uani 1 1 d .
H3 H 0.3232 0.3006 0.5576 0.028 Uiso 1 1 calc R
C4 C 0.45488(11) 0.35007(5) 0.51095(16) 0.0178(2) Uani 1 1 d .
C5 C 0.56945(11) 0.34747(5) 0.49433(18) 0.0209(2) Uani 1 1 d .
H5 H 0.6081 0.3822 0.4771 0.025 Uiso 1 1 calc R
C6 C 0.62808(11) 0.29460(5) 0.50258(18) 0.0221(3) Uani 1 1 d .
H6 H 0.7060 0.2927 0.4904 0.027 Uiso 1 1 calc R
C7 C 0.39015(10) 0.40790(5) 0.48874(16) 0.0169(2) Uani 1 1 d .
H7 H 0.4507 0.4397 0.5155 0.020 Uiso 1 1 calc R
C8 C 0.39626(12) 0.43695(5) 0.79831(17) 0.0225(3) Uani 1 1 d .
H8A H 0.4819 0.4288 0.8182 0.027 Uiso 1 1 calc R
H8B H 0.3728 0.4214 0.9023 0.027 Uiso 1 1 calc R
C9 C 0.37149(11) 0.50206(5) 0.77659(18) 0.0233(3) Uani 1 1 d .
H9A H 0.3785 0.5208 0.8950 0.028 Uiso 1 1 calc R
H9B H 0.4260 0.5215 0.7189 0.028 Uiso 1 1 calc R
C10 C 0.24426(12) 0.50287(5) 0.65376(17) 0.0210(2) Uani 1 1 d .
C11 C 0.10949(11) 0.42502(6) 0.48324(19) 0.0244(3) Uani 1 1 d .
H11A H 0.0496 0.4562 0.4421 0.029 Uiso 1 1 calc R
H11B H 0.0874 0.4019 0.5766 0.029 Uiso 1 1 calc R
C12 C 0.10682(11) 0.38678(5) 0.32559(17) 0.0196(2) Uani 1 1 d .
H12 H 0.0370 0.3641 0.2776 0.024 Uiso 1 1 calc R
C13 C 0.19207(10) 0.38110(5) 0.24494(16) 0.0165(2) Uani 1 1 d .
C14 C 0.30707(10) 0.41584(5) 0.29312(16) 0.0165(2) Uani 1 1 d .
H14 H 0.3527 0.4008 0.2119 0.020 Uiso 1 1 calc R
C15 C 0.28694(11) 0.48046(5) 0.24753(17) 0.0183(2) Uani 1 1 d .
C16 C 0.15815(13) 0.55032(5) 0.06043(19) 0.0272(3) Uani 1 1 d .
H16A H 0.1084 0.5518 -0.0683 0.033 Uiso 1 1 calc R
H16B H 0.2329 0.5718 0.0714 0.033 Uiso 1 1 calc R
C17 C 0.09278(15) 0.57839(6) 0.1785(2) 0.0353(3) Uani 1 1 d .
H17A H 0.0180 0.5576 0.1655 0.053 Uiso 1 1 calc R
H17B H 0.0753 0.6189 0.1413 0.053 Uiso 1 1 calc R
H17C H 0.1423 0.5770 0.3057 0.053 Uiso 1 1 calc R
C18 C 0.17346(11) 0.34230(5) 0.08407(16) 0.0177(2) Uani 1 1 d .
C19 C 0.05405(12) 0.27092(5) -0.10513(18) 0.0239(3) Uani 1 1 d .
H19A H 0.1172 0.2414 -0.0920 0.029 Uiso 1 1 calc R
H19B H 0.0509 0.2954 -0.2121 0.029 Uiso 1 1 calc R
C20 C -0.06418(12) 0.24200(6) -0.12965(19) 0.0263(3) Uani 1 1 d .
H20A H -0.0582 0.2155 -0.0278 0.039 Uiso 1 1 calc R
H20B H -0.0868 0.2201 -0.2439 0.039 Uiso 1 1 calc R
H20C H -0.1248 0.2715 -0.1332 0.039 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
C15 O5 C16 116.45(10)
C18 O7 C19 114.94(10)
O1 N1 O2 123.52(11)
O1 N1 C1 118.17(11)
O2 N1 C1 118.31(10)
N3 N2 C8 103.07(9)
N3 N2 C7 110.11(9)
C8 N2 C7 111.04(10)
C10 N3 N2 113.99(10)
C10 N3 C11 124.53(10)
N2 N3 C11 115.58(9)
C2 C1 C6 122.68(11)
C2 C1 N1 118.59(11)
C6 C1 N1 118.73(11)
C1 C2 C3 118.32(11)
C1 C2 H2 120.8
C3 C2 H2 120.8
C2 C3 C4 120.90(12)
C2 C3 H3 119.6
C4 C3 H3 119.6
C5 C4 C3 119.11(11)
C5 C4 C7 119.58(10)
C3 C4 C7 121.28(11)
C6 C5 C4 120.88(11)
C6 C5 H5 119.6
C4 C5 H5 119.6
C1 C6 C5 118.07(12)
C1 C6 H6 121.0
C5 C6 H6 121.0
N2 C7 C4 108.44(9)
N2 C7 C14 111.28(9)
C4 C7 C14 111.33(9)
N2 C7 H7 108.6
C4 C7 H7 108.6
C14 C7 H7 108.6
N2 C8 C9 104.85(10)
N2 C8 H8A 110.8
C9 C8 H8A 110.8
N2 C8 H8B 110.8
C9 C8 H8B 110.8
H8A C8 H8B 108.9
C10 C9 C8 101.60(10)
C10 C9 H9A 111.4
C8 C9 H9A 111.4
C10 C9 H9B 111.5
C8 C9 H9B 111.4
H9A C9 H9B 109.3
O3 C10 N3 124.50(12)
O3 C10 C9 128.87(11)
N3 C10 C9 106.62(10)
N3 C11 C12 112.32(10)
N3 C11 H11A 109.1
C12 C11 H11A 109.1
N3 C11 H11B 109.1
C12 C11 H11B 109.1
H11A C11 H11B 107.9
C13 C12 C11 126.92(11)
C13 C12 H12 116.5
C11 C12 H12 116.5
C12 C13 C18 120.15(11)
C12 C13 C14 124.91(11)
C18 C13 C14 114.71(10)
C13 C14 C15 113.03(9)
C13 C14 C7 115.70(9)
C15 C14 C7 110.41(9)
C13 C14 H14 105.6
C15 C14 H14 105.6
C7 C14 H14 105.6
O4 C15 O5 124.21(11)
O4 C15 C14 123.69(11)
O5 C15 C14 111.98(10)
O5 C16 C17 110.17(11)
O5 C16 H16A 109.6
C17 C16 H16A 109.6
O5 C16 H16B 109.6
C17 C16 H16B 109.6
H16A C16 H16B 108.1
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
O6 C18 O7 122.82(11)
O6 C18 C13 123.54(11)
O7 C18 C13 113.64(10)
O7 C19 C20 107.61(10)
O7 C19 H19A 110.2
C20 C19 H19A 110.2
O7 C19 H19B 110.2
C20 C19 H19B 110.2
H19A C19 H19B 108.5
C19 C20 H20A 109.5
C19 C20 H20B 109.5
H20A C20 H20B 109.5
C19 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.2273(14)
O2 N1 1.2272(15)
O3 C10 1.2208(15)
O4 C15 1.2097(15)
O5 C15 1.3320(15)
O5 C16 1.4647(14)
O6 C18 1.2100(15)
O7 C18 1.3438(14)
O7 C19 1.4566(14)
N1 C1 1.4747(15)
N2 N3 1.4307(14)
N2 C8 1.4905(16)
N2 C7 1.4912(16)
N3 C10 1.3695(15)
N3 C11 1.4460(16)
C1 C2 1.3787(18)
C1 C6 1.3865(17)
C2 C3 1.3878(17)
C2 H2 0.9500
C3 C4 1.3966(16)
C3 H3 0.9500
C4 C5 1.3922(17)
C4 C7 1.5189(15)
C5 C6 1.3921(16)
C5 H5 0.9500
C6 H6 0.9500
C7 C14 1.5425(16)
C7 H7 1.0000
C8 C9 1.5281(18)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.5125(18)
C9 H9A 0.9900
C9 H9B 0.9900
C11 C12 1.4935(17)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.3346(17)
C12 H12 0.9500
C13 C18 1.4905(16)
C13 C14 1.5190(16)
C14 C15 1.5320(16)
C14 H14 1.0000
C16 C17 1.502(2)
C16 H16A 0.9900
C16 H16B 0.9900
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C19 C20 1.5020(18)
C19 H19A 0.9900
C19 H19B 0.9900
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 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
C8 N2 N3 C10 14.02(13)
C7 N2 N3 C10 -104.50(11)
C8 N2 N3 C11 -140.26(11)
C7 N2 N3 C11 101.22(12)
O1 N1 C1 C2 -7.56(17)
O2 N1 C1 C2 172.28(12)
O1 N1 C1 C6 172.93(12)
O2 N1 C1 C6 -7.23(17)
C6 C1 C2 C3 1.0(2)
N1 C1 C2 C3 -178.52(11)
C1 C2 C3 C4 0.7(2)
C2 C3 C4 C5 -2.1(2)
C2 C3 C4 C7 175.77(12)
C3 C4 C5 C6 2.02(19)
C7 C4 C5 C6 -175.92(12)
C2 C1 C6 C5 -1.1(2)
N1 C1 C6 C5 178.42(11)
C4 C5 C6 C1 -0.46(19)
N3 N2 C7 C4 -156.42(9)
C8 N2 C7 C4 90.07(11)
N3 N2 C7 C14 -33.64(12)
C8 N2 C7 C14 -147.16(9)
C5 C4 C7 N2 -141.36(11)
C3 C4 C7 N2 40.74(15)
C5 C4 C7 C14 95.89(13)
C3 C4 C7 C14 -82.01(14)
N3 N2 C8 C9 -27.81(12)
C7 N2 C8 C9 90.06(11)
N2 C8 C9 C10 31.02(12)
N2 N3 C10 O3 -172.98(12)
C11 N3 C10 O3 -21.4(2)
N2 N3 C10 C9 6.06(14)
C11 N3 C10 C9 157.69(12)
C8 C9 C10 O3 156.16(14)
C8 C9 C10 N3 -22.83(13)
C10 N3 C11 C12 152.16(12)
N2 N3 C11 C12 -56.61(15)
N3 C11 C12 C13 -8.86(19)
C11 C12 C13 C18 -177.90(12)
C11 C12 C13 C14 -3.74(19)
C12 C13 C14 C15 -66.71(15)
C18 C13 C14 C15 107.73(11)
C12 C13 C14 C7 61.97(15)
C18 C13 C14 C7 -123.59(11)
N2 C7 C14 C13 -45.82(13)
C4 C7 C14 C13 75.28(12)
N2 C7 C14 C15 84.14(11)
C4 C7 C14 C15 -154.76(10)
C16 O5 C15 O4 -3.63(18)
C16 O5 C15 C14 -179.73(10)
C13 C14 C15 O4 158.93(12)
C7 C14 C15 O4 27.56(16)
C13 C14 C15 O5 -24.94(14)
C7 C14 C15 O5 -156.31(10)
C15 O5 C16 C17 -86.91(14)
C19 O7 C18 O6 -3.67(16)
C19 O7 C18 C13 175.95(9)
C12 C13 C18 O6 166.16(12)
C14 C13 C18 O6 -8.56(16)
C12 C13 C18 O7 -13.46(15)
C14 C13 C18 O7 171.82(9)
C18 O7 C19 C20 -170.25(10)
