#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:07:09 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180375 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/44/7204459.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_7204459
loop_
_publ_author_name
'Chong, Hyun-soon'
'Ganguly, Bishwajit'
'Broker, Grant A.'
'Rogers, Robin D.'
'Brechbiel, Martin W.'
_publ_section_title
;
 Stereoselective and regioselective synthesis of azepane and azepine
 derivatives via piperidine ring expansion
;
_journal_issue                   18
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2080
_journal_paper_doi               10.1039/b204677f
_journal_year                    2002
_chemical_formula_moiety         'C28 H35 N3 O4 S2, C H2 Cl2'
_chemical_formula_sum            'C29 H37 Cl2 N3 O4 S2'
_chemical_formula_weight         626.64
_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                79.037(13)
_cell_angle_beta                 88.444(13)
_cell_angle_gamma                65.605(11)
_cell_formula_units_Z            2
_cell_length_a                   10.245(8)
_cell_length_b                   10.338(8)
_cell_length_c                   15.970(12)
_cell_measurement_reflns_used    975
_cell_measurement_temperature    173(2)
_cell_volume                     1510(2)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6846
_diffrn_reflns_theta_full        23.27
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.393
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_type   SADABS
_exptl_absorpt_process_details
;    
2-theta dependent absorption corrections applied for an effective sphere
with mu*diameter =   0.040
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         4308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0629P)²+1.1604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1096
_reflns_number_gt                3814
_reflns_number_total             4308
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b204677f.txt
_cod_data_source_block           g1obal
_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_original_cell_volume        1509.7(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204459
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
Cl1 Cl 0.14330(8) -0.38691(8) 0.13713(6) 0.0534(2) Uani 1 1 d . . .
Cl2 Cl -0.15602(8) -0.19937(9) 0.15271(6) 0.0565(2) Uani 1 1 d . . .
S1 S 0.57811(6) 0.55991(6) 0.10532(4) 0.02730(18) Uani 1 1 d . . .
S2 S 0.16823(7) 0.19592(7) 0.37504(4) 0.03470(19) Uani 1 1 d . . .
O1 O 0.43426(18) 0.64921(17) 0.07029(10) 0.0329(4) Uani 1 1 d . . .
O2 O 0.69233(19) 0.58979(19) 0.06438(11) 0.0363(4) Uani 1 1 d . . .
O3 O 0.0490(2) 0.3178(2) 0.32940(13) 0.0461(5) Uani 1 1 d . . .
O4 O 0.2068(2) 0.1954(2) 0.46066(12) 0.0453(5) Uani 1 1 d . . .
N1 N 0.6211(2) 0.3893(2) 0.10735(14) 0.0286(5) Uani 1 1 d . . .
H1N1 H 0.652(3) 0.372(3) 0.057(2) 0.045(8) Uiso 1 1 d . . .
N2 N 0.4701(2) 0.1205(2) 0.18198(13) 0.0265(4) Uani 1 1 d . . .
N3 N 0.3038(2) 0.1785(2) 0.31778(15) 0.0327(5) Uani 1 1 d . . .
H1N3 H 0.281(3) 0.214(3) 0.2691(18) 0.028(8) Uiso 1 1 d . . .
C1 C 0.5855(3) 0.1719(3) 0.17291(16) 0.0282(5) Uani 1 1 d . . .
H1C H 0.6504 0.1251 0.1292 0.034 Uiso 1 1 calc R . .
C2 C 0.4882(3) -0.0004(3) 0.25241(16) 0.0295(6) Uani 1 1 d . . .
H2B H 0.5905 -0.0697 0.2595 0.035 Uiso 1 1 calc R . .
H2C H 0.4316 -0.0516 0.2379 0.035 Uiso 1 1 calc R . .
C3 C 0.4407(3) 0.0494(3) 0.33657(16) 0.0310(6) Uani 1 1 d . . .
H3C H 0.4210 -0.0285 0.3746 0.037 Uiso 1 1 calc R . .
C4 C 0.5496(3) 0.0778(3) 0.38479(17) 0.0367(6) Uani 1 1 d . . .
H4B H 0.5070 0.1121 0.4371 0.044 Uiso 1 1 calc R . .
H4C H 0.6351 -0.0147 0.4027 0.044 Uiso 1 1 calc R . .
C5 C 0.5974(3) 0.1887(3) 0.33305(17) 0.0387(6) Uani 1 1 d . . .
H5A H 0.6608 0.2075 0.3702 0.046 Uiso 1 1 calc R . .
H5B H 0.5120 0.2808 0.3143 0.046 Uiso 1 1 calc R . .
C6 C 0.6772(3) 0.1400(3) 0.25459(17) 0.0350(6) Uani 1 1 d . . .
H6A H 0.7358 0.0342 0.2696 0.042 Uiso 1 1 calc R . .
H6B H 0.7445 0.1869 0.2419 0.042 Uiso 1 1 calc R . .
C7 C 0.5129(3) 0.3347(3) 0.13773(16) 0.0279(5) Uani 1 1 d . . .
H7A H 0.4433 0.3548 0.0900 0.033 Uiso 1 1 calc R . .
H7B H 0.4598 0.3852 0.1830 0.033 Uiso 1 1 calc R . .
C8 C 0.5809(3) 0.5700(2) 0.21417(15) 0.0265(5) Uani 1 1 d . . .
C9 C 0.4558(3) 0.6478(3) 0.25054(16) 0.0303(6) Uani 1 1 d . . .
H9A H 0.3666 0.6910 0.2181 0.036 Uiso 1 1 calc R . .
C10 C 0.4615(3) 0.6621(3) 0.33447(16) 0.0323(6) Uani 1 1 d . . .
H10A H 0.3753 0.7145 0.3596 0.039 Uiso 1 1 calc R . .
C11 C 0.5908(3) 0.6013(3) 0.38290(16) 0.0322(6) Uani 1 1 d . . .
C12 C 0.7157(3) 0.5219(3) 0.34488(16) 0.0338(6) Uani 1 1 d . . .
H12A H 0.8051 0.4787 0.3771 0.041 Uiso 1 1 calc R . .
C13 C 0.7112(3) 0.5054(3) 0.26147(16) 0.0311(6) Uani 1 1 d . . .
H13A H 0.7966 0.4503 0.2366 0.037 Uiso 1 1 calc R . .
C14 C 0.5971(3) 0.6198(3) 0.47367(18) 0.0464(7) Uani 1 1 d . . .
H14A H 0.4998 0.6736 0.4905 0.070 Uiso 1 1 calc R . .
H14B H 0.6554 0.6734 0.4782 0.070 Uiso 1 1 calc R . .
H14C H 0.6404 0.5244 0.5114 0.070 Uiso 1 1 calc R . .
C15 C 0.4333(3) 0.0937(3) 0.10007(16) 0.0302(6) Uani 1 1 d . . .
H15A H 0.4992 -0.0055 0.0939 0.036 Uiso 1 1 calc R . .
H15B H 0.4475 0.1627 0.0525 0.036 Uiso 1 1 calc R . .
C16 C 0.2807(3) 0.1098(3) 0.09388(15) 0.0277(5) Uani 1 1 d . . .
C17 C 0.2494(3) -0.0058(3) 0.08645(16) 0.0329(6) Uani 1 1 d . . .
H17A H 0.3256 -0.0976 0.0855 0.039 Uiso 1 1 calc R . .
C18 C 0.1087(3) 0.0104(3) 0.08032(17) 0.0382(6) Uani 1 1 d . . .
H18A H 0.0890 -0.0702 0.0758 0.046 Uiso 1 1 calc R . .
C19 C -0.0027(3) 0.1429(3) 0.08081(18) 0.0407(7) Uani 1 1 d . . .
H19A H -0.0992 0.1539 0.0765 0.049 Uiso 1 1 calc R . .
C20 C 0.0260(3) 0.2599(3) 0.08752(17) 0.0380(6) Uani 1 1 d . . .
H20A H -0.0509 0.3515 0.0879 0.046 Uiso 1 1 calc R . .
C21 C 0.1664(3) 0.2440(3) 0.09368(16) 0.0335(6) Uani 1 1 d . . .
H21A H 0.1853 0.3252 0.0978 0.040 Uiso 1 1 calc R . .
C22 C 0.1376(3) 0.0384(3) 0.37999(16) 0.0329(6) Uani 1 1 d . . .
C23 C 0.0920(3) 0.0131(3) 0.30606(18) 0.0394(6) Uani 1 1 d . . .
H23A H 0.0805 0.0780 0.2532 0.047 Uiso 1 1 calc R . .
C24 C 0.0634(3) -0.1072(3) 0.30995(19) 0.0422(7) Uani 1 1 d . . .
H24A H 0.0324 -0.1242 0.2592 0.051 Uiso 1 1 calc R . .
C25 C 0.0788(3) -0.2041(3) 0.38658(19) 0.0407(7) Uani 1 1 d . . .
C26 C 0.1275(3) -0.1783(3) 0.45919(18) 0.0418(7) Uani 1 1 d . . .
H26A H 0.1412 -0.2443 0.5119 0.050 Uiso 1 1 calc R . .
C27 C 0.1563(3) -0.0579(3) 0.45624(17) 0.0377(6) Uani 1 1 d . . .
H27A H 0.1890 -0.0417 0.5067 0.045 Uiso 1 1 calc R . .
C28 C 0.0441(4) -0.3332(4) 0.3900(2) 0.0571(8) Uani 1 1 d . . .
H28A H 0.1172 -0.4039 0.3615 0.086 Uiso 1 1 calc R . .
H28B H -0.0502 -0.3017 0.3610 0.086 Uiso 1 1 calc R . .
H28C H 0.0426 -0.3778 0.4497 0.086 Uiso 1 1 calc R . .
C29 C -0.0319(3) -0.3757(3) 0.1468(2) 0.0494(8) Uani 1 1 d . . .
H29A H -0.0346 -0.4439 0.1989 0.059 Uiso 1 1 calc R . .
H29B H -0.0597 -0.4050 0.0970 0.059 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'
S S 0.1246 0.1234 '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
O1 S1 O2 117.51(12) . . ?
O1 S1 N1 111.83(11) . . ?
O2 S1 N1 105.70(11) . . ?
O1 S1 C8 107.15(11) . . ?
O2 S1 C8 110.13(11) . . ?
N1 S1 C8 103.67(11) . . ?
O3 S2 O4 119.35(12) . . ?
O3 S2 N3 106.04(13) . . ?
O4 S2 N3 108.69(13) . . ?
O3 S2 C22 108.93(13) . . ?
O4 S2 C22 106.21(12) . . ?
N3 S2 C22 107.08(12) . . ?
C7 N1 S1 116.48(16) . . ?
C2 N2 C1 117.33(19) . . ?
C2 N2 C15 111.34(19) . . ?
C1 N2 C15 111.14(18) . . ?
C3 N3 S2 121.67(19) . . ?
N2 C1 C7 106.40(19) . . ?
N2 C1 C6 115.5(2) . . ?
C7 C1 C6 110.5(2) . . ?
N2 C2 C3 112.4(2) . . ?
N3 C3 C4 111.4(2) . . ?
N3 C3 C2 107.2(2) . . ?
C4 C3 C2 115.5(2) . . ?
C5 C4 C3 113.9(2) . . ?
C4 C5 C6 113.2(2) . . ?
C5 C6 C1 116.8(2) . . ?
N1 C7 C1 110.1(2) . . ?
C9 C8 C13 120.6(2) . . ?
C9 C8 S1 120.27(19) . . ?
C13 C8 S1 119.07(19) . . ?
C10 C9 C8 119.4(2) . . ?
C9 C10 C11 121.3(2) . . ?
C10 C11 C12 118.1(2) . . ?
C10 C11 C14 121.2(2) . . ?
C12 C11 C14 120.7(2) . . ?
C13 C12 C11 121.1(2) . . ?
C12 C13 C8 119.4(2) . . ?
N2 C15 C16 112.35(19) . . ?
C17 C16 C21 118.2(2) . . ?
C17 C16 C15 121.5(2) . . ?
C21 C16 C15 120.3(2) . . ?
C18 C17 C16 121.0(2) . . ?
C19 C18 C17 120.2(2) . . ?
C18 C19 C20 119.8(3) . . ?
C19 C20 C21 120.1(3) . . ?
C20 C21 C16 120.7(2) . . ?
C27 C22 C23 119.8(3) . . ?
C27 C22 S2 121.0(2) . . ?
C23 C22 S2 119.2(2) . . ?
C24 C23 C22 119.5(3) . . ?
C23 C24 C25 121.5(3) . . ?
C26 C25 C24 117.9(3) . . ?
C26 C25 C28 121.3(3) . . ?
C24 C25 C28 120.8(3) . . ?
C27 C26 C25 121.2(3) . . ?
C22 C27 C26 120.0(3) . . ?
Cl1 C29 Cl2 111.68(16) . . ?
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 C29 1.755(3) . ?
Cl2 C29 1.759(3) . ?
S1 O1 1.436(2) . ?
S1 O2 1.4396(19) . ?
S1 N1 1.626(2) . ?
S1 C8 1.763(3) . ?
S2 O3 1.428(2) . ?
S2 O4 1.432(2) . ?
S2 N3 1.608(2) . ?
S2 C22 1.768(3) . ?
N1 C7 1.471(3) . ?
N2 C2 1.465(3) . ?
N2 C1 1.477(3) . ?
N2 C15 1.477(3) . ?
N3 C3 1.471(3) . ?
C1 C7 1.527(3) . ?
C1 C6 1.530(4) . ?
C2 C3 1.526(4) . ?
C3 C4 1.526(4) . ?
C4 C5 1.523(4) . ?
C5 C6 1.528(4) . ?
C8 C9 1.383(4) . ?
C8 C13 1.388(4) . ?
C9 C10 1.382(4) . ?
C10 C11 1.390(4) . ?
C11 C12 1.400(4) . ?
C11 C14 1.504(4) . ?
C12 C13 1.379(4) . ?
C15 C16 1.506(4) . ?
C16 C17 1.385(4) . ?
C16 C21 1.398(4) . ?
C17 C18 1.385(4) . ?
C18 C19 1.375(4) . ?
C19 C20 1.381(4) . ?
C20 C21 1.383(4) . ?
C22 C27 1.380(4) . ?
C22 C23 1.389(4) . ?
C23 C24 1.380(4) . ?
C24 C25 1.393(4) . ?
C25 C26 1.387(4) . ?
C25 C28 1.508(4) . ?
C26 C27 1.385(4) . ?
