#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/70/1507078.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_1507078
loop_
_publ_author_name
'He, Ling'
'Chan, Philip Wai Hong'
'Tsui, Wai-Man'
'Yu, Wing-Yiu'
'Che, Chi-Ming'
_publ_section_title
;
 Ruthenium(II) porphyrin-catalyzed amidation of aromatic heterocycles.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2405
_journal_page_last               2408
_journal_paper_doi               10.1021/ol049232j
_journal_volume                  6
_journal_year                    2004
_chemical_formula_moiety         'C18 H20 N3 O3 S'
_chemical_formula_sum            'C18 H20 N3 O3 S'
_chemical_formula_weight         358.43
_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                 101.95(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.785(2)
_cell_length_b                   6.1130(12)
_cell_length_c                   25.017(5)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    253(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1763.2(6)
_computing_cell_refinement       Scalepack
_computing_data_collection       Marcontrol
_computing_data_reduction        Denzo
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Shelxs-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      253(2)
_diffrn_measured_fraction_theta_full 0.841
_diffrn_measured_fraction_theta_max 0.841
_diffrn_measurement_device_type  'marresearch IPDS mar300'
_diffrn_measurement_method       Oscillation
_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  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            9460
_diffrn_reflns_theta_full        25.41
_diffrn_reflns_theta_max         25.41
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0546
_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)+(0.0970P)²+0.2485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1638
_reflns_number_gt                2117
_reflns_number_total             2740
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol049232jsi20040427_125843.cif
_cod_data_source_block           mar1068
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1507078
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
S1 S 0.35549(6) 0.58372(10) 0.31326(3) 0.0420(3) Uani 0.957(3) 1 d P
O1 O 0.42141(19) 0.6199(3) 0.36758(8) 0.0623(6) Uani 1 1 d .
O2 O 0.3213(2) 0.7727(3) 0.27921(9) 0.0613(6) Uani 1 1 d .
N1 N 0.42971(19) 0.4110(3) 0.28703(8) 0.0437(6) Uani 1 1 d .
N2 N 0.35310(19) 0.4111(3) 0.14328(8) 0.0419(6) Uani 1 1 d .
N3 N 0.38307(18) 0.3785(3) 0.23106(8) 0.0393(5) Uani 1 1 d .
C1 C 0.4050(2) 0.5013(4) 0.19062(10) 0.0417(6) Uani 1 1 d .
H1 H 0.4491 0.6287 0.1946 0.050 Uiso 1 1 calc R
C2 C 0.3161(2) 0.2023(4) 0.20899(11) 0.0460(7) Uani 1 1 d .
H2 H 0.2891 0.0903 0.2282 0.055 Uiso 1 1 calc R
C3 C 0.2974(2) 0.2237(4) 0.15442(11) 0.0473(7) Uani 1 1 d .
H3 H 0.2547 0.1292 0.1288 0.057 Uiso 1 1 calc R
C4 C 0.2239(2) 0.4557(4) 0.31969(10) 0.0435(7) Uani 1 1 d .
C5 C 0.2265(3) 0.2478(5) 0.34214(12) 0.0546(8) Uani 1 1 d .
H5 H 0.2964 0.1732 0.3526 0.066 Uiso 1 1 calc R
C6 C 0.1229(3) 0.1521(6) 0.34884(13) 0.0661(9) Uani 1 1 d .
H6 H 0.1246 0.0126 0.3638 0.079 Uiso 1 1 calc R
C7 C 0.0171(3) 0.2601(6) 0.33371(13) 0.0661(9) Uani 1 1 d .
C8 C 0.0171(3) 0.4625(6) 0.31012(15) 0.0701(10) Uani 1 1 d .
H8 H -0.0530 0.5355 0.2987 0.084 Uiso 1 1 calc R
C9 C 0.1183(3) 0.5611(5) 0.30288(13) 0.0587(8) Uani 1 1 d .
H9 H 0.1157 0.6984 0.2867 0.070 Uiso 1 1 calc R
C10 C -0.0933(3) 0.1550(8) 0.34230(17) 0.0989(14) Uani 1 1 d .
H10A H -0.1059 0.1927 0.3779 0.148 Uiso 1 1 calc R
H10B H -0.0872 -0.0010 0.3396 0.148 Uiso 1 1 calc R
H10C H -0.1573 0.2064 0.3150 0.148 Uiso 1 1 calc R
C11 C 0.3592(2) 0.4953(5) 0.09038(11) 0.0479(7) Uani 1 1 d .
C12 C 0.3205(3) 0.3656(6) 0.04449(13) 0.0695(10) Uani 1 1 d .
H12 H 0.2896 0.2273 0.0476 0.083 Uiso 1 1 calc R
C13 C 0.3293(4) 0.4494(8) -0.00614(14) 0.0896(13) Uani 1 1 d .
H13 H 0.3044 0.3647 -0.0372 0.107 Uiso 1 1 calc R
C14 C 0.3737(4) 0.6534(8) -0.01147(15) 0.0879(12) Uani 1 1 d .
H14 H 0.3780 0.7070 -0.0458 0.105 Uiso 1 1 calc R
C15 C 0.4119(3) 0.7782(6) 0.03442(15) 0.0787(11) Uani 1 1 d .
H15 H 0.4426 0.9164 0.0310 0.094 Uiso 1 1 calc R
C16 C 0.4052(3) 0.7008(5) 0.08555(13) 0.0600(8) Uani 1 1 d .
H16 H 0.4313 0.7861 0.1164 0.072 Uiso 1 1 calc R
O3 O 0.0900(11) 0.0245(19) 0.0464(5) 0.179(4) Uiso 0.50 1 d P
O4 O -0.1107(11) 0.112(2) 0.0502(5) 0.204(5) Uiso 0.50 1 d P
C17 C 0.0061(18) 0.022(4) 0.0275(7) 0.158(6) Uiso 0.50 1 d P
C18 C -0.0620(14) 0.225(3) 0.0324(6) 0.156(5) Uiso 0.50 1 d P
C19 C 0.0270(17) 0.124(3) -0.0010(11) 0.188(7) Uiso 0.50 1 d P
C20 C -0.025(2) 0.402(3) 0.0185(9) 0.229(9) Uiso 0.50 1 d P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
O1 S1 O2 117.77(13) . .
O1 S1 N1 104.82(13) . .
O2 S1 N1 113.37(12) . .
O1 S1 C4 107.10(13) . .
O2 S1 C4 105.33(14) . .
N1 S1 C4 108.01(12) . .
N3 N1 S1 111.59(16) . .
C1 N2 C3 108.3(2) . .
C1 N2 C11 124.6(2) . .
C3 N2 C11 127.0(2) . .
C1 N3 C2 108.8(2) . .
C1 N3 N1 125.5(2) . .
C2 N3 N1 125.5(2) . .
N3 C1 N2 108.5(2) . .
C3 C2 N3 106.8(2) . .
C2 C3 N2 107.6(2) . .
C9 C4 C5 119.5(3) . .
C9 C4 S1 120.9(2) . .
C5 C4 S1 119.6(2) . .
C4 C5 C6 119.1(3) . .
C7 C6 C5 121.7(3) . .
C8 C7 C6 117.7(3) . .
C8 C7 C10 121.6(4) . .
C6 C7 C10 120.7(4) . .
C7 C8 C9 121.8(3) . .
C8 C9 C4 120.2(3) . .
C16 C11 C12 120.9(3) . .
C16 C11 N2 120.1(3) . .
C12 C11 N2 119.0(3) . .
C13 C12 C11 117.9(4) . .
C14 C13 C12 121.8(4) . .
C13 C14 C15 119.3(3) . .
C14 C15 C16 120.8(4) . .
C15 C16 C11 119.4(3) . .
C17 O3 C19 46.4(14) . .
C17 O3 C19 33.1(13) . 3
C19 O3 C19 59.6(15) . 3
C18 O4 C17 61.0(13) . .
O3 C17 C19 88(2) . .
O3 C17 C19 118(2) . 3
C19 C17 C19 100(3) . 3
O3 C17 C17 111(2) . 3
C19 C17 C17 53.9(17) . 3
C19 C17 C17 46.3(15) 3 3
O3 C17 C18 116(2) . .
C19 C17 C18 76(2) . .
C19 C17 C18 125(2) 3 .
C17 C17 C18 107(2) 3 .
O3 C17 O4 129.1(18) . .
C19 C17 O4 112(2) . .
C19 C17 O4 104(2) 3 .
C17 C17 O4 119(2) 3 .
C18 C17 O4 38.2(8) . .
O4 C18 C20 160(2) . .
O4 C18 C17 80.8(15) . .
C20 C18 C17 118(2) . .
O4 C18 C19 116.3(18) . .
C20 C18 C19 83.2(17) . .
C17 C18 C19 38.2(9) . .
C17 C19 C17 80(3) . 3
C17 C19 O3 45.7(15) . .
C17 C19 O3 102(2) 3 .
C17 C19 C18 65.6(18) . .
C17 C19 C18 115(2) 3 .
O3 C19 C18 90.9(16) . .
C17 C19 C19 42.5(16) . 3
C17 C19 C19 37.2(13) 3 3
O3 C19 C19 73.4(17) . 3
C18 C19 C19 92.3(19) . 3
C17 C19 O3 83(2) . 3
C17 C19 O3 28.9(11) 3 3
O3 C19 O3 120.4(15) . 3
C18 C19 O3 91.4(11) . 3
C19 C19 O3 47.1(13) 3 3
C17 C19 C20 103(2) . .
C17 C19 C20 140.1(19) 3 .
O3 C19 C20 108.2(17) . .
C18 C19 C20 40.6(10) . .
C19 C19 C20 132(2) 3 .
O3 C19 C20 111.3(13) 3 .
C18 C20 C20 162(3) . 3_565
C18 C20 C19 56.2(12) . .
C20 C20 C19 109.0(18) 3_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.436(2) .
S1 O2 1.442(2) .
S1 N1 1.596(2) .
S1 C4 1.774(3) .
N1 N3 1.409(3) .
N2 C1 1.334(3) .
N2 C3 1.377(3) .
N2 C11 1.436(3) .
N3 C1 1.328(3) .
N3 C2 1.381(3) .
C2 C3 1.343(4) .
C4 C9 1.387(4) .
C4 C5 1.387(4) .
C5 C6 1.395(4) .
C6 C7 1.393(5) .
C7 C8 1.371(5) .
C7 C10 1.506(5) .
C8 C9 1.382(4) .
C11 C16 1.383(4) .
C11 C12 1.392(4) .
C12 C13 1.390(5) .
C13 C14 1.370(6) .
C14 C15 1.374(5) .
C15 C16 1.381(4) .
O3 C17 1.004(18) .
O3 C19 1.40(2) .
O3 C19 1.83(3) 3
O4 C18 1.055(18) .
O4 C17 1.69(2) .
C17 C19 1.01(2) .
C17 C19 1.134(18) 3
C17 C17 1.38(3) 3
C17 C18 1.49(2) .
C18 C20 1.25(2) .
C18 C19 1.59(3) .
C19 C17 1.134(18) 3
C19 C19 1.65(4) 3
C19 O3 1.83(3) 3
C19 C20 1.90(3) .
C20 C20 1.69(4) 3_565
