#------------------------------------------------------------------------------
#$Date: 2016-03-21 16:56:25 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178761 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/15/4101598.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_4101598
loop_
_publ_author_name
'Liang, Yong'
'Jiao, Lei'
'Zhang, Shiwei'
'Yu, Zhi-Xiang'
'Xu, Jiaxi'
_publ_section_title
;
 New Insights into the Torquoselectivity of the Staudinger Reaction
;
_journal_issue                   4
_journal_name_full               'JOURNAL OF THE AMERICAN CHEMICAL SOCIETY'
_journal_page_first              1542
_journal_page_last               1549
_journal_paper_doi               10.1021/ja808046e
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C18 H14 Cl N O3'
_chemical_formula_weight         327.75
_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                 102.10(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.082(3)
_cell_length_b                   12.461(3)
_cell_length_c                   7.8035(16)
_cell_measurement_reflns_used    8224
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      3.06
_cell_volume                     1529.0(5)
_computing_cell_refinement       Rapid-AUTO
_computing_data_collection       'Rapid-AUTO (Rigaku,2000)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC,2000)'
_computing_molecular_graphics    'Siemens SHELXTL V4.2,(Sheldrick,1990)'
_computing_publication_material  SHELXL-97,(Sheldrick,1997)
_computing_structure_refinement  SHELXL-97,(Sheldrick,1997)
_computing_structure_solution    SHELXS-97,(Sheldrick,1997)
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       Ω
_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  0.0599
_diffrn_reflns_av_sigmaI/netI    0.0802
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8224
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
                                  HIGASHI, T. (1995). Abscor-Empirical
                                  Absorption Correction based on Fourier
                                  Series Approximation.
                                  Rigaku Corporation,Tokyo,Japan.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0133(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   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0434
_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)+(0.0250P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0901
_reflns_number_gt                1310
_reflns_number_total             2678
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            reformated.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4101598
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.06044(5) 0.62590(7) 0.00026(13) 0.0903(3) Uani 1 1 d . . .
O1 O 0.38162(11) 0.80475(14) -0.1130(2) 0.0570(5) Uani 1 1 d . . .
O2 O 0.13667(11) 1.01667(15) 0.0545(3) 0.0683(6) Uani 1 1 d . . .
O3 O 0.30924(12) 1.11805(15) 0.2649(3) 0.0704(6) Uani 1 1 d . . .
N1 N 0.33409(13) 0.98556(16) 0.0633(3) 0.0449(6) Uani 1 1 d . . .
C1 C 0.30548(17) 0.7641(2) -0.0805(3) 0.0486(7) Uani 1 1 d . . .
C2 C 0.29562(18) 0.6545(2) -0.0777(3) 0.0571(8) Uani 1 1 d . . .
H2 H 0.3400 0.6095 -0.0907 0.069 Uiso 1 1 calc R . .
C3 C 0.21939(19) 0.6115(2) -0.0554(3) 0.0598(8) Uani 1 1 d . . .
H3 H 0.2114 0.5376 -0.0546 0.072 Uiso 1 1 calc R . .
C4 C 0.15560(17) 0.6806(2) -0.0342(4) 0.0558(8) Uani 1 1 d . . .
C5 C 0.16497(17) 0.7908(2) -0.0370(4) 0.0536(8) Uani 1 1 d . . .
H5 H 0.1206 0.8355 -0.0226 0.064 Uiso 1 1 calc R . .
C6 C 0.24079(16) 0.8340(2) -0.0613(3) 0.0457(7) Uani 1 1 d . . .
C7 C 0.26015(16) 0.9509(2) -0.0757(4) 0.0497(7) Uani 1 1 d . . .
H7 H 0.2704 0.9673 -0.1923 0.060 Uiso 1 1 calc R . .
C8 C 0.41631(17) 0.9421(2) 0.1123(4) 0.0429(7) Uani 1 1 d . . .
C9 C 0.47638(17) 0.9875(2) 0.2466(4) 0.0528(8) Uani 1 1 d . . .
H9 H 0.4633 1.0490 0.3032 0.063 Uiso 1 1 calc R . .
C10 C 0.55622(17) 0.9405(2) 0.2959(4) 0.0591(8) Uani 1 1 d . . .
H10 H 0.5966 0.9712 0.3853 0.071 Uiso 1 1 calc R . .
C11 C 0.57630(18) 0.8493(2) 0.2145(4) 0.0609(8) Uani 1 1 d . . .
H11 H 0.6297 0.8181 0.2495 0.073 Uiso 1 1 calc R . .
C12 C 0.51700(18) 0.8042(2) 0.0805(4) 0.0558(8) Uani 1 1 d . . .
H12 H 0.5306 0.7430 0.0240 0.067 Uiso 1 1 calc R . .
C13 C 0.43724(17) 0.8502(2) 0.0301(4) 0.0474(7) Uani 1 1 d . . .
C14 C 0.29029(17) 1.0615(2) 0.1358(4) 0.0524(8) Uani 1 1 d . . .
C15 C 0.20976(18) 1.0437(2) -0.0099(4) 0.0543(8) Uani 1 1 d . . .
C16 C 0.18468(19) 1.1375(2) -0.1353(4) 0.0786(10) Uani 1 1 d . . .
H16A H 0.2319 1.1865 -0.1313 0.094 Uiso 1 1 calc R . .
H16B H 0.1648 1.1127 -0.2547 0.094 Uiso 1 1 calc R . .
C17 C 0.1149(2) 1.1887(3) -0.0661(5) 0.0982(12) Uani 1 1 d . . .
H17A H 0.1370 1.2436 0.0194 0.118 Uiso 1 1 calc R . .
H17B H 0.0733 1.2209 -0.1601 0.118 Uiso 1 1 calc R . .
C18 C 0.0772(2) 1.1011(3) 0.0153(6) 0.1163(16) Uani 1 1 d . . .
H18A H 0.0615 1.1261 0.1219 0.140 Uiso 1 1 calc R . .
H18B H 0.0262 1.0758 -0.0639 0.140 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'
Cl Cl 0.1484 0.1585 '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
C1 O1 C13 116.19(19) . . ?
C18 O2 C15 108.8(2) . . ?
C14 N1 C8 133.6(2) . . ?
C14 N1 C7 95.7(2) . . ?
C8 N1 C7 130.2(2) . . ?
C2 C1 C6 121.9(3) . . ?
C2 C1 O1 118.1(3) . . ?
C6 C1 O1 119.8(2) . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 118.5(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 122.2(3) . . ?
C3 C4 Cl1 118.3(2) . . ?
C5 C4 Cl1 119.5(2) . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 118.2(3) . . ?
C5 C6 C7 126.3(2) . . ?
C1 C6 C7 115.4(2) . . ?
N1 C7 C6 111.9(2) . . ?
N1 C7 C15 86.35(19) . . ?
C6 C7 C15 124.5(2) . . ?
N1 C7 H7 110.5 . . ?
C6 C7 H7 110.5 . . ?
C15 C7 H7 110.5 . . ?
C13 C8 C9 119.2(3) . . ?
C13 C8 N1 119.8(3) . . ?
C9 C8 N1 121.0(2) . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 119.7(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 119.9(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 120.7(3) . . ?
C12 C13 O1 117.3(3) . . ?
C8 C13 O1 121.8(2) . . ?
O3 C14 N1 132.9(3) . . ?
O3 C14 C15 135.8(3) . . ?
N1 C14 C15 91.2(2) . . ?
O2 C15 C16 106.5(2) . . ?
O2 C15 C14 113.7(2) . . ?
C16 C15 C14 115.4(2) . . ?
O2 C15 C7 118.0(2) . . ?
C16 C15 C7 116.3(2) . . ?
C14 C15 C7 86.3(2) . . ?
C17 C16 C15 102.4(3) . . ?
C17 C16 H16A 111.3 . . ?
C15 C16 H16A 111.3 . . ?
C17 C16 H16B 111.3 . . ?
C15 C16 H16B 111.3 . . ?
H16A C16 H16B 109.2 . . ?
C18 C17 C16 104.6(3) . . ?
C18 C17 H17A 110.8 . . ?
C16 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
C16 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?
O2 C18 C17 109.1(2) . . ?
O2 C18 H18A 109.9 . . ?
C17 C18 H18A 109.9 . . ?
O2 C18 H18B 109.9 . . ?
C17 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
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
Cl1 C4 1.747(3) . ?
O1 C1 1.397(3) . ?
O1 C13 1.396(3) . ?
O2 C18 1.412(3) . ?
O2 C15 1.413(3) . ?
O3 C14 1.215(3) . ?
N1 C14 1.371(3) . ?
N1 C8 1.405(3) . ?
N1 C7 1.495(3) . ?
C1 C2 1.375(3) . ?
C1 C6 1.389(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.499(3) . ?
C7 C15 1.559(3) . ?
C7 H7 0.9800 . ?
C8 C13 1.388(3) . ?
C8 C9 1.388(3) . ?
C9 C10 1.390(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(3) . ?
C12 H12 0.9300 . ?
C14 C15 1.550(4) . ?
C15 C16 1.523(4) . ?
C16 C17 1.488(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.457(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
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
C13 O1 C1 C2 -107.5(3) . . . . ?
C13 O1 C1 C6 75.8(3) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
O1 C1 C2 C3 -176.5(2) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C2 C3 C4 Cl1 -178.2(2) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
Cl1 C4 C5 C6 178.9(2) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C4 C5 C6 C7 177.1(3) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
O1 C1 C6 C5 177.2(2) . . . . ?
C2 C1 C6 C7 -177.3(3) . . . . ?
O1 C1 C6 C7 -0.7(4) . . . . ?
C14 N1 C7 C6 -120.6(2) . . . . ?
C8 N1 C7 C6 52.0(3) . . . . ?
C14 N1 C7 C15 5.2(2) . . . . ?
C8 N1 C7 C15 177.8(2) . . . . ?
C5 C6 C7 N1 120.8(3) . . . . ?
C1 C6 C7 N1 -61.5(3) . . . . ?
C5 C6 C7 C15 19.7(4) . . . . ?
C1 C6 C7 C15 -162.6(3) . . . . ?
C14 N1 C8 C13 167.2(2) . . . . ?
C7 N1 C8 C13 -2.6(4) . . . . ?
C14 N1 C8 C9 -10.4(4) . . . . ?
C7 N1 C8 C9 179.8(2) . . . . ?
C13 C8 C9 C10 0.2(4) . . . . ?
N1 C8 C9 C10 177.8(2) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C12 0.8(4) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C11 C12 C13 C8 0.5(4) . . . . ?
C11 C12 C13 O1 176.3(2) . . . . ?
C9 C8 C13 C12 -0.2(4) . . . . ?
N1 C8 C13 C12 -177.9(2) . . . . ?
C9 C8 C13 O1 -175.9(2) . . . . ?
N1 C8 C13 O1 6.5(3) . . . . ?
C1 O1 C13 C12 119.4(3) . . . . ?
C1 O1 C13 C8 -64.9(3) . . . . ?
C8 N1 C14 O3 1.9(5) . . . . ?
C7 N1 C14 O3 174.1(3) . . . . ?
C8 N1 C14 C15 -177.4(3) . . . . ?
C7 N1 C14 C15 -5.2(2) . . . . ?
C18 O2 C15 C16 -14.6(3) . . . . ?
C18 O2 C15 C14 113.6(3) . . . . ?
C18 O2 C15 C7 -147.5(3) . . . . ?
O3 C14 C15 O2 -55.3(4) . . . . ?
N1 C14 C15 O2 124.0(2) . . . . ?
O3 C14 C15 C16 68.2(4) . . . . ?
N1 C14 C15 C16 -112.5(2) . . . . ?
O3 C14 C15 C7 -174.3(3) . . . . ?
N1 C14 C15 C7 4.99(19) . . . . ?
N1 C7 C15 O2 -119.6(2) . . . . ?
C6 C7 C15 O2 -5.4(4) . . . . ?
N1 C7 C15 C16 112.1(3) . . . . ?
C6 C7 C15 C16 -133.8(3) . . . . ?
N1 C7 C15 C14 -4.58(18) . . . . ?
C6 C7 C15 C14 109.6(3) . . . . ?
O2 C15 C16 C17 26.9(3) . . . . ?
C14 C15 C16 C17 -100.3(3) . . . . ?
C7 C15 C16 C17 160.7(2) . . . . ?
C15 C16 C17 C18 -28.6(4) . . . . ?
C15 O2 C18 C17 -4.1(4) . . . . ?
C16 C17 C18 O2 21.3(4) . . . . ?
