#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/74/1507476.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_1507476
loop_
_publ_author_name
'Yamada, Ken-ichi'
'Fujihara, Hidetaka'
'Yamamoto, Yasutomo'
'Miwa, Yoshihisa'
'Taga, Tooru'
'Tomioka, Kiyoshi'
_publ_section_title
;
 Radical Addition of Ethers to Imines Initiated by Dimethylzinc
;
_journal_issue                   20
_journal_name_full               'Organic Letters'
_journal_page_first              3509
_journal_paper_doi               10.1021/ol0266572
_journal_volume                  4
_journal_year                    2002
_chemical_compound_source        synthetic
_chemical_formula_sum            'C18 H20 Cl N O3 S'
_chemical_formula_weight         365.86
_chemical_name_common            gouseiyamada
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                98.16(2)
_cell_angle_beta                 101.84(2)
_cell_angle_gamma                84.16(2)
_cell_formula_units_Z            2
_cell_length_a                   10.218(2)
_cell_length_b                   11.247(3)
_cell_length_c                   8.086(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295.0
_cell_measurement_theta_max      24.89
_cell_measurement_theta_min      22.81
_cell_volume                     897.7(4)
_computing_cell_refinement       NSC/AFC
_computing_data_collection       Rigaku/AFC5
_computing_data_reduction        NSC/AFC
_computing_molecular_graphics    KPPXRAY
_computing_publication_material  EDCIF-J
_computing_structure_refinement  'Full Matrix Least Squares'
_computing_structure_solution    MULTAN88
_diffrn_ambient_temperature      295.0
_diffrn_measurement_device       diffractometer
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphaite
_diffrn_radiation_source         rotarix
_diffrn_radiation_type           CU
_diffrn_radiation_wavelength     1.54051
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2812
_diffrn_reflns_reduction_process NSC/AFC
_diffrn_reflns_theta_max         60
_diffrn_reflns_theta_min         1
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 56
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.3532
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.45
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.02
_refine_ls_hydrogen_treatment    'refxyz from D-map'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         2557
_refine_ls_R_factor_obs          0.051
_refine_ls_shift/esd_max         0.08
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=1/(σ²(F)+0.023)
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.063
_reflns_number_total             2719
_reflns_observed_criterion       F>3\s(F)
_cod_data_source_file            ol0266572_s2.cif
_cod_data_source_block           GOUSEI
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w=1/(\s^2^(F)+0.023)' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w=1/(\s^2^(F)+0.023)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        897.7
_cod_original_formula_sum        'C18 H20 O3 N1 S1 Cl1'
_cod_database_code               1507476
loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
-X,-Y,-Z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
Cl1 1.1664(1) 0.1426(1) 0.3533(2) .0920(5) Ueq
S1 0.51348(8) 0.32054(7) 0.5980(1) .0392(4) Ueq
C1 0.7990(5) 0.6601(4) 0.9478(6) .065(2) Ueq
C2 0.7757(6) 0.6225(5) 1.1089(7) .073(2) Ueq
C3 0.7331(5) 0.4955(4) 1.0524(5) .062(2) Ueq
C4 0.8196(4) 0.4495(3) 0.9215(5) .046(1) Ueq
C5 0.7603(3) 0.3551(3) 0.7787(4) .042(1) Ueq
C6 0.8602(3) 0.3027(3) 0.6659(4) .040(1) Ueq
C7 0.8854(4) 0.3630(3) 0.5395(5) .053(1) Ueq
C8 0.9808(4) 0.3144(4) 0.4420(5) .059(2) Ueq
C9 1.0483(4) 0.2056(3) 0.4757(5) .055(1) Ueq
C10 1.0259(4) 0.1456(4) 0.6000(5) .058(2) Ueq
C11 0.9303(4) 0.1944(3) 0.6949(5) .051(1) Ueq
C12 0.6964(8) 0.0095(6) 0.0016(9) .089(3) Ueq
C13 0.6476(4) 0.0867(3) 0.1501(5) .054(2) Ueq
C14 0.6409(4) 0.0378(4) 0.2940(6) .060(2) Ueq
C15 0.5988(4) 0.1084(3) 0.4322(5) .051(1) Ueq
C16 0.5621(3) 0.2284(3) 0.4212(4) .039(1) Ueq
C17 0.5659(4) 0.2778(3) 0.2776(5) .052(1) Ueq
C18 0.6082(4) 0.2055(4) 0.1432(5) .060(2) Ueq
N1 0.6340(3) 0.4053(3) 0.6869(4) .041(1) Ueq
O1 0.5001(2) 0.2434(2) 0.7174(3) .0506(9) Ueq
O2 0.4027(2) 0.4019(2) 0.5356(3) .0491(9) Ueq
O3 0.8408(2) 0.5522(2) 0.8479(3) .0544(9) Ueq
H1 0.624(4) 0.474(3) 0.638(5) .08(1) Uiso
H1A 0.874(4) 0.720(4) 0.977(5) .09(1) Uiso
H1B 0.713(5) 0.697(4) 0.874(6) .10(1) Uiso
H2A 0.713(4) 0.678(3) 1.134(5) .08(1) Uiso
H2B 0.860(5) 0.625(4) 1.191(5) .09(1) Uiso
H3A 0.627(4) 0.498(3) 0.992(5) .08(1) Uiso
H3B 0.749(4) 0.451(3) 1.141(5) .05(1) Uiso
H4 0.903(4) 0.414(3) 0.979(4) .06(1) Uiso
H5 0.741(3) 0.285(3) 0.835(4) .041(9) Uiso
H7 0.837(3) 0.439(3) 0.505(4) .06(1) Uiso
H8 0.999(4) 0.354(3) 0.349(5) .06(1) Uiso
H10 1.074(4) 0.071(3) 0.621(5) .08(1) Uiso
H11 0.914(3) 0.150(3) 0.783(4) .05(1) Uiso
H12A 0.685(5) 0.039(5) -0.095(7) .13(3) Uiso
H12B 0.647(5) -0.063(4) -0.039(6) .11(3) Uiso
H12C 0.785(5) -0.004(5) 0.032(6) .11(3) Uiso
H14 0.664(3) -0.045(3) 0.305(4) .06(1) Uiso
H15 0.597(3) 0.071(3) 0.533(4) .06(1) Uiso
H17 0.551(4) 0.359(3) 0.271(4) .06(1) Uiso
H18 0.610(4) 0.243(3) 0.053(5) .08(1) Uiso
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 36 0.017 0.009 International_Tables_Vol_IV_Table_2.2B
H 0 40 0.000 0.000 International_Tables_Vol_IV_Table_2.2B
O 0 6 0.047 0.032 International_Tables_Vol_IV_Table_2.2B
N 0 2 0.029 0.018 International_Tables_Vol_IV_Table_2.2B
S 0 2 0.319 0.557 International_Tables_Vol_IV_Table_2.2B
CL 0 2 0.355 1.423 International_Tables_Vol_IV_Table_2.2B
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C16 S1 N1 108.3(2) yes
C16 S1 O1 107.4(2) yes
C16 S1 O2 108.2(1) yes
N1 S1 O1 107.4(2) yes
N1 S1 O2 105.2(1) yes
O1 S1 O2 119.9(1) yes
C2 C1 O3 106.4(4) yes
C1 C2 C3 102.7(4) yes
C2 C3 C4 101.8(4) yes
C3 C4 C5 115.8(3) yes
C3 C4 O3 106.1(3) yes
C5 C4 O3 108.5(3) yes
C4 C5 C6 112.3(3) yes
C4 C5 N1 109.2(3) yes
C6 C5 N1 114.3(3) yes
C5 C6 C7 121.9(3) yes
C5 C6 C11 118.9(3) yes
C7 C6 C11 119.2(3) yes
C6 C7 C8 120.5(3) yes
C7 C8 C9 118.2(4) yes
Cl1 C9 C8 118.8(3) yes
Cl1 C9 C10 119.0(3) yes
C8 C9 C10 122.2(4) yes
C9 C10 C11 119.0(4) yes
C6 C11 C10 120.9(4) yes
C12 C13 C14 120.6(4) yes
C12 C13 C18 121.0(4) yes
C14 C13 C18 118.4(4) yes
C13 C14 C15 121.1(4) yes
C14 C15 C16 118.7(4) yes
S1 C16 C15 119.3(3) yes
S1 C16 C17 119.8(3) yes
C15 C16 C17 120.9(3) yes
C16 C17 C18 119.0(3) yes
C13 C18 C17 122.0(4) yes
S1 N1 C5 121.2(3) yes
C1 O3 C4 109.6(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
CL1 C9 1.748(4) yes
S1 C16 1.769(3) yes
S1 N1 1.620(3) yes
S1 O1 1.421(3) yes
S1 O2 1.435(2) yes
C1 C2 1.496(8) yes
C1 O3 1.437(5) yes
C2 C3 1.516(7) yes
C3 C4 1.518(6) yes
C4 C5 1.524(5) yes
C4 O3 1.426(5) yes
C5 C6 1.526(5) yes
C5 N1 1.454(4) yes
C6 C7 1.382(6) yes
C6 C11 1.373(5) yes
C7 C8 1.398(6) yes
C8 C9 1.376(5) yes
C9 C10 1.355(6) yes
C10 C11 1.387(6) yes
C12 C13 1.519(8) yes
C13 C14 1.372(7) yes
C13 C18 1.361(6) yes
C14 C15 1.393(6) yes
C15 C16 1.374(5) yes
C16 C17 1.365(6) yes
C17 C18 1.378(6) yes
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_publ_flag
Cl1 C9 C10 C11 -178.7(3) no
S1 C16 C17 C18 177.9(3) no
C1 C2 C3 C4 36.0(4) no
C2 C1 O3 C4 11.2(4) no
C2 C3 C4 C5 -150.6(3) no
C2 C3 C4 O3 -30.2(4) no
C3 C4 C5 C6 -172.9(3) no
C3 C4 C5 N1 59.3(4) no
C3 C4 O3 C1 12.3(4) no
C4 C5 C6 C7 -79.7(4) no
C4 C5 C6 C11 98.1(4) no
C4 C5 N1 S1 -149.3(3) no
C5 C4 O3 C1 137.3(3) no
C5 C6 C7 C8 177.9(3) no
C5 C6 C11 C10 -177.5(3) no
C6 C5 N1 S1 84.1(4) no
C6 C7 C8 C9 -0.1(4) no
C7 C6 C11 C10 0.3(5) no
C7 C8 C9 CL1 179.2(3) no
C7 C8 C9 C10 -0.5(6) no
C8 C9 C10 C11 1.0(6) no
C9 C10 C11 C6 -0.9(5) no
C11 C6 C7 C8 0.1(5) no
C12 C13 C14 C15 178.7(5) no
C12 C13 C18 C17 -178.8(5) no
C13 C14 C15 C16 0.9(6) no
C14 C13 C18 C17 1.9(6) no
C14 C15 C16 S1 -178.0(3) no
C14 C15 C16 C17 0.4(5) no
C15 C16 C17 C18 -0.4(5) no
C16 S1 N1 C5 -70.0(3) no
C16 C17 C18 C13 -0.7(6) no
C18 C13 C14 C15 -1.9(6) no
N1 S1 C16 C15 105.9(3) no
N1 S1 C16 C17 -72.5(3) no
N1 C5 C6 C7 45.3(4) no
N1 C5 C6 C11 -137.0(3) no
O1 S1 C16 C15 -9.8(3) no
O1 S1 C16 C17 171.8(3) no
O1 S1 N1 C5 45.7(3) no
O2 S1 C16 C15 -140.6(3) no
O2 S1 C16 C17 41.1(3) no
O2 S1 N1 C5 174.5(3) no
O3 C1 C2 C3 -29.9(5) no
O3 C4 C5 C6 68.0(3) no
O3 C4 C5 N1 -59.8(4) no
