#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:56:18 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178412 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/33/4023378.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_4023378
loop_
_publ_author_name
'Yun-Yun Yang'
'Wang-Ge Shou'
'Deng Hong'
'Yan-Guang Wang'
_publ_section_title
;
 Selective Synthesis of 4-Alkylidene-β-lactams and
 N,N'-Diarylamidines from Azides and Aryloxyacetyl Chlorides via a
 Ketenimine-Participating One-Pot Cascade Process
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3574
_journal_page_last               3577
_journal_paper_doi               10.1021/jo702733h
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C23 H19 N O3'
_chemical_formula_weight         357.39
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                104.469(2)
_cell_angle_beta                 91.025(2)
_cell_angle_gamma                105.824(2)
_cell_formula_units_Z            2
_cell_length_a                   6.7674(8)
_cell_length_b                   11.3499(13)
_cell_length_c                   13.1617(15)
_cell_measurement_reflns_used    2190
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.958
_cell_measurement_theta_min      5.644
_cell_volume                     937.76(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1474
_diffrn_reflns_av_sigmaI/netI    0.1061
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5169
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75045
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.422
_exptl_crystal_size_min          0.349
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.058(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0716
_refine_ls_shift/su_max          0.044
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1249P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1932
_refine_ls_wR_factor_ref         0.2076
_reflns_number_gt                2728
_reflns_number_total             3619
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702733h-File003.cif
_cod_data_source_block           cd2706
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023378
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.2585(2) 1.10960(16) 0.04876(12) 0.0744(5) Uani 1 1 d . . .
O2 O 1.0400(2) 1.27106(13) 0.21721(12) 0.0648(4) Uani 1 1 d . . .
O3 O 0.8527(2) 0.94010(16) 0.35017(12) 0.0698(5) Uani 1 1 d . . .
N1 N 1.0800(2) 0.99434(16) 0.16120(12) 0.0555(4) Uani 1 1 d . . .
C1 C 1.1321(3) 1.0882(2) 0.10923(15) 0.0576(5) Uani 1 1 d . . .
C2 C 0.9629(3) 1.14480(19) 0.15730(16) 0.0572(5) Uani 1 1 d . . .
H2 H 0.8479 1.1320 0.1056 0.069 Uiso 1 1 calc R . .
C3 C 0.9263(3) 1.04331(19) 0.21558(15) 0.0555(5) Uani 1 1 d . . .
C4 C 0.8204(3) 1.0217(2) 0.29528(16) 0.0611(5) Uani 1 1 d . . .
H4 H 0.7205 1.0632 0.3148 0.073 Uiso 1 1 calc R . .
C5 C 0.6933(3) 0.88313(19) 0.40232(15) 0.0575(5) Uani 1 1 d . . .
C6 C 0.7534(4) 0.8454(2) 0.48637(18) 0.0690(6) Uani 1 1 d . . .
H6 H 0.8927 0.8613 0.5065 0.083 Uiso 1 1 calc R . .
C7 C 0.6051(4) 0.7838(2) 0.54042(19) 0.0800(7) Uani 1 1 d . . .
H7 H 0.6442 0.7588 0.5980 0.096 Uiso 1 1 calc R . .
C8 C 0.4006(4) 0.7591(2) 0.5099(2) 0.0825(8) Uani 1 1 d . . .
H8 H 0.3006 0.7154 0.5453 0.099 Uiso 1 1 calc R . .
C9 C 0.3442(4) 0.7987(3) 0.4274(2) 0.0832(7) Uani 1 1 d . . .
H9 H 0.2049 0.7840 0.4081 0.100 Uiso 1 1 calc R . .
C10 C 0.4905(3) 0.8605(2) 0.37184(17) 0.0704(6) Uani 1 1 d . . .
H10 H 0.4510 0.8861 0.3147 0.084 Uiso 1 1 calc R . .
C11 C 0.9023(3) 1.33856(18) 0.25370(15) 0.0546(5) Uani 1 1 d . . .
C12 C 0.6994(3) 1.3054(2) 0.21359(18) 0.0645(6) Uani 1 1 d . . .
H12 H 0.6443 1.2314 0.1601 0.077 Uiso 1 1 calc R . .
C13 C 0.5791(3) 1.3832(2) 0.2538(2) 0.0746(7) Uani 1 1 d . . .
H13 H 0.4427 1.3618 0.2261 0.090 Uiso 1 1 calc R . .
C14 C 0.6567(4) 1.4914(2) 0.3335(2) 0.0775(7) Uani 1 1 d . . .
H14 H 0.5742 1.5435 0.3597 0.093 Uiso 1 1 calc R . .
C15 C 0.8572(4) 1.5222(2) 0.3744(2) 0.0760(7) Uani 1 1 d . . .
H15 H 0.9105 1.5949 0.4294 0.091 Uiso 1 1 calc R . .
C16 C 0.9806(3) 1.4459(2) 0.33449(18) 0.0676(6) Uani 1 1 d . . .
H16 H 1.1169 1.4674 0.3624 0.081 Uiso 1 1 calc R . .
C17 C 1.1302(3) 0.87810(19) 0.14486(14) 0.0554(5) Uani 1 1 d . . .
C18 C 1.3153(3) 0.8694(2) 0.10417(16) 0.0635(6) Uani 1 1 d . . .
H18 H 1.4059 0.9391 0.0886 0.076 Uiso 1 1 calc R . .
C19 C 1.3626(4) 0.7559(3) 0.08722(17) 0.0726(7) Uani 1 1 d . . .
H19 H 1.4859 0.7497 0.0595 0.087 Uiso 1 1 calc R . .
C20 C 1.2319(4) 0.6510(3) 0.11030(18) 0.0752(7) Uani 1 1 d . . .
C21 C 1.0482(4) 0.6622(2) 0.14932(19) 0.0756(6) Uani 1 1 d . . .
H21 H 0.9583 0.5926 0.1653 0.091 Uiso 1 1 calc R . .
C22 C 0.9940(3) 0.7735(2) 0.16526(18) 0.0658(6) Uani 1 1 d . . .
H22 H 0.8673 0.7780 0.1895 0.079 Uiso 1 1 calc R . .
C23 C 1.2889(6) 0.5286(3) 0.0957(3) 0.1130(11) Uani 1 1 d . . .
H23A H 1.1807 0.4675 0.1168 0.129 Uiso 1 1 calc R . .
H23B H 1.4149 0.5441 0.1381 0.129 Uiso 1 1 calc R . .
H23C H 1.3074 0.4964 0.0229 0.129 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 C2 118.80(15) . . ?
C4 O3 C5 118.79(16) . . ?
C1 N1 C17 130.75(16) . . ?
C1 N1 C3 93.75(15) . . ?
C17 N1 C3 134.03(16) . . ?
O1 C1 N1 132.0(2) . . ?
O1 C1 C2 136.9(2) . . ?
N1 C1 C2 91.13(15) . . ?
O2 C2 C3 117.25(17) . . ?
O2 C2 C1 112.91(15) . . ?
C3 C2 C1 84.80(14) . . ?
O2 C2 H2 113.0 . . ?
C3 C2 H2 113.0 . . ?
C1 C2 H2 113.0 . . ?
C4 C3 N1 134.7(2) . . ?
C4 C3 C2 134.4(2) . . ?
N1 C3 C2 90.14(14) . . ?
C3 C4 O3 122.04(19) . . ?
C3 C4 H4 119.0 . . ?
O3 C4 H4 119.0 . . ?
C10 C5 C6 121.2(2) . . ?
C10 C5 O3 123.56(19) . . ?
C6 C5 O3 115.24(19) . . ?
C5 C6 C7 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 121.0(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C5 C10 C9 118.7(2) . . ?
C5 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C16 C11 C12 120.06(19) . . ?
C16 C11 O2 115.43(17) . . ?
C12 C11 O2 124.51(19) . . ?
C13 C12 C11 119.2(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 119.2(2) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C16 120.4(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 119.9(2) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C22 C17 C18 120.3(2) . . ?
C22 C17 N1 120.56(17) . . ?
C18 C17 N1 119.09(19) . . ?
C19 C18 C17 119.0(2) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C20 121.8(2) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C21 C20 C19 117.8(2) . . ?
C21 C20 C23 120.7(3) . . ?
C19 C20 C23 121.5(2) . . ?
C22 C21 C20 122.0(2) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C21 C22 C17 119.1(2) . . ?
C21 C22 H22 120.5 . . ?
C17 C22 H22 120.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.196(2) . ?
O2 C11 1.381(2) . ?
O2 C2 1.400(2) . ?
O3 C4 1.366(3) . ?
O3 C5 1.386(2) . ?
N1 C1 1.377(2) . ?
N1 C17 1.417(3) . ?
N1 C3 1.430(2) . ?
C1 C2 1.532(3) . ?
C2 C3 1.506(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.317(3) . ?
C4 H4 0.9300 . ?
C5 C10 1.359(3) . ?
C5 C6 1.374(3) . ?
C6 C7 1.376(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.360(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C16 1.370(3) . ?
C11 C12 1.378(3) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.380(3) . ?
C17 C18 1.390(3) . ?
C18 C19 1.376(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(3) . ?
C20 C23 1.509(4) . ?
C21 C22 1.377(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 N1 C1 O1 -14.2(4) . . . . ?
C3 N1 C1 O1 178.5(2) . . . . ?
C17 N1 C1 C2 164.0(2) . . . . ?
C3 N1 C1 C2 -3.34(15) . . . . ?
C11 O2 C2 C3 -92.1(2) . . . . ?
C11 O2 C2 C1 171.77(16) . . . . ?
O1 C1 C2 O2 -61.4(3) . . . . ?
N1 C1 C2 O2 120.61(17) . . . . ?
O1 C1 C2 C3 -178.8(3) . . . . ?
N1 C1 C2 C3 3.18(14) . . . . ?
C1 N1 C3 C4 -167.3(2) . . . . ?
C17 N1 C3 C4 26.1(4) . . . . ?
C1 N1 C3 C2 3.40(15) . . . . ?
C17 N1 C3 C2 -163.3(2) . . . . ?
O2 C2 C3 C4 54.5(3) . . . . ?
C1 C2 C3 C4 167.7(2) . . . . ?
O2 C2 C3 N1 -116.19(17) . . . . ?
C1 C2 C3 N1 -3.06(14) . . . . ?
N1 C3 C4 O3 3.5(4) . . . . ?
C2 C3 C4 O3 -163.3(2) . . . . ?
C5 O3 C4 C3 -154.90(19) . . . . ?
C4 O3 C5 C10 27.2(3) . . . . ?
C4 O3 C5 C6 -155.23(18) . . . . ?
C10 C5 C6 C7 0.0(3) . . . . ?
O3 C5 C6 C7 -177.7(2) . . . . ?
C5 C6 C7 C8 0.8(4) . . . . ?
C6 C7 C8 C9 -1.7(4) . . . . ?
C7 C8 C9 C10 1.9(4) . . . . ?
C6 C5 C10 C9 0.2(3) . . . . ?
O3 C5 C10 C9 177.6(2) . . . . ?
C8 C9 C10 C5 -1.1(4) . . . . ?
C2 O2 C11 C16 162.25(18) . . . . ?
C2 O2 C11 C12 -18.6(3) . . . . ?
C16 C11 C12 C13 1.8(3) . . . . ?
O2 C11 C12 C13 -177.37(19) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 C16 1.0(4) . . . . ?
C12 C11 C16 C15 -1.2(3) . . . . ?
O2 C11 C16 C15 178.03(19) . . . . ?
C14 C15 C16 C11 -0.2(4) . . . . ?
C1 N1 C17 C22 -147.9(2) . . . . ?
C3 N1 C17 C22 14.4(3) . . . . ?
C1 N1 C17 C18 29.7(3) . . . . ?
C3 N1 C17 C18 -167.96(19) . . . . ?
C22 C17 C18 C19 -1.6(3) . . . . ?
N1 C17 C18 C19 -179.24(18) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C18 C19 C20 C21 1.3(4) . . . . ?
C18 C19 C20 C23 -177.4(2) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C23 C20 C21 C22 178.8(3) . . . . ?
C20 C21 C22 C17 -2.1(4) . . . . ?
C18 C17 C22 C21 2.9(3) . . . . ?
N1 C17 C22 C21 -179.50(19) . . . . ?
