#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/57/1515759.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_1515759
loop_
_publ_author_name
'Miura, Tomoya'
'Funakoshi, Yuuta'
'Tanaka, Takamasa'
'Murakami, Masahiro'
_publ_section_title
;
 Direct Production of Enaminones from Terminal Alkynes via
 Rhodium-Catalyzed Reaction of Formamides with N-Sulfonyl-1,2,3-triazoles.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2760
_journal_page_last               2763
_journal_paper_doi               10.1021/ol5010774
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C18 H20 N2 O3 S'
_chemical_formula_weight         344.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 103.988(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5437(6)
_cell_length_b                   22.8556(14)
_cell_length_c                   9.3763(7)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.03
_cell_volume                     1776.6(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'Yadokari-XG (Wakita, 2000)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, 2000)'
_computing_publication_material  'Yadokari-XG (Wakita, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16278
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.8727
_exptl_absorpt_correction_T_min  0.8564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.70
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         4068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0603
_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)+(0.0579P)²+0.4581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1238
_reflns_number_gt                3209
_reflns_number_total             4068
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol5010774_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 1515759.cif.'
_cod_original_sg_symbol_Hall     -p_2yn
_cod_original_sg_symbol_H-M      p_21/n
_cod_database_code               1515759
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.71800(5) 0.375050(19) 0.59907(5) 0.01577(13) Uani 1 1 d .
O2 O 0.38472(14) 0.45946(6) 0.38067(15) 0.0175(3) Uani 1 1 d .
N7 N 0.70030(18) 0.43337(7) 0.49438(17) 0.0138(3) Uani 1 1 d .
O4 O 0.84143(16) 0.33847(6) 0.56528(17) 0.0229(3) Uani 1 1 d .
O5 O 0.73791(16) 0.39591(6) 0.74723(15) 0.0223(3) Uani 1 1 d .
N6 N 0.87362(18) 0.40491(7) 0.25335(18) 0.0179(3) Uani 1 1 d .
C7 C 0.4575(2) 0.43768(7) 0.2938(2) 0.0134(4) Uani 1 1 d .
C8 C 0.1609(2) 0.40462(9) -0.1378(2) 0.0229(4) Uani 1 1 d .
H1 H 0.0942 0.3976 -0.2304 0.027 Uiso 1 1 calc R
C9 C 0.3624(2) 0.42603(8) 0.1391(2) 0.0145(4) Uani 1 1 d .
C10 C 0.2694(2) 0.47101(8) 0.0612(2) 0.0205(4) Uani 1 1 d .
H2 H 0.2739 0.5083 0.1018 0.025 Uiso 1 1 calc R
C11 C 0.5364(2) 0.33492(7) 0.5474(2) 0.0153(4) Uani 1 1 d .
C12 C 0.4068(2) 0.34982(8) 0.6056(2) 0.0194(4) Uani 1 1 d .
H3 H 0.4147 0.3809 0.6708 0.023 Uiso 1 1 calc R
C13 C 0.6286(2) 0.42514(7) 0.3399(2) 0.0134(4) Uani 1 1 d .
C14 C 0.2650(2) 0.31739(8) 0.5645(2) 0.0199(4) Uani 1 1 d .
H4 H 0.1789 0.3265 0.6051 0.024 Uiso 1 1 calc R
C15 C 0.3529(2) 0.37008(8) 0.0783(2) 0.0171(4) Uani 1 1 d .
H5 H 0.4140 0.3398 0.1300 0.020 Uiso 1 1 calc R
C16 C 0.2518(2) 0.35947(8) -0.0600(2) 0.0202(4) Uani 1 1 d .
H6 H 0.2454 0.3221 -0.1001 0.024 Uiso 1 1 calc R
C17 C 0.5242(2) 0.28899(8) 0.4480(2) 0.0221(4) Uani 1 1 d .
H7 H 0.6115 0.2793 0.4096 0.027 Uiso 1 1 calc R
C18 C 0.7151(2) 0.40911(8) 0.2400(2) 0.0162(4) Uani 1 1 d .
H19 H 0.6522 0.3996 0.1473 0.019 Uiso 1 1 calc R
C19 C 0.2496(2) 0.27169(8) 0.4642(2) 0.0207(4) Uani 1 1 d .
C20 C 0.1696(2) 0.46026(9) -0.0775(2) 0.0248(4) Uani 1 1 d .
H8 H 0.1087 0.4905 -0.1297 0.030 Uiso 1 1 calc R
C21 C 0.3808(3) 0.25771(8) 0.4065(2) 0.0256(5) Uani 1 1 d .
H9 H 0.3723 0.2272 0.3395 0.031 Uiso 1 1 calc R
C22 C 0.9341(3) 0.37721(10) 0.1363(3) 0.0306(5) Uani 1 1 d .
H10 H 0.9855 0.3409 0.1713 0.046 Uiso 1 1 calc R
H11 H 1.0106 0.4027 0.1079 0.046 Uiso 1 1 calc R
H12 H 0.8458 0.3700 0.0531 0.046 Uiso 1 1 calc R
C23 C 0.9949(2) 0.42911(10) 0.3767(2) 0.0262(5) Uani 1 1 d .
H13 H 0.9552 0.4648 0.4088 0.039 Uiso 1 1 calc R
H14 H 1.0923 0.4369 0.3461 0.039 Uiso 1 1 calc R
H15 H 1.0168 0.4015 0.4562 0.039 Uiso 1 1 calc R
C24 C 0.0930(3) 0.23818(10) 0.4189(3) 0.0330(5) Uani 1 1 d .
H16 H 0.0437 0.2458 0.3172 0.050 Uiso 1 1 calc R
H17 H 0.0215 0.2504 0.4780 0.050 Uiso 1 1 calc R
H18 H 0.1141 0.1971 0.4326 0.050 Uiso 1 1 calc R
H20 H 0.654(3) 0.4606(10) 0.533(3) 0.023(6) Uiso 1 1 d .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O5 S1 O4 118.86(9)
O5 S1 N7 106.30(8)
O4 S1 N7 107.86(8)
O5 S1 C11 109.12(9)
O4 S1 C11 106.24(8)
N7 S1 C11 108.06(8)
C13 N7 S1 116.76(12)
C18 N6 C23 123.83(16)
C18 N6 C22 119.67(17)
C23 N6 C22 116.44(16)
O2 C7 C13 120.82(16)
O2 C7 C9 117.60(15)
C13 C7 C9 121.57(15)
C20 C8 C16 119.97(18)
C10 C9 C15 119.51(17)
C10 C9 C7 118.78(16)
C15 C9 C7 121.40(16)
C9 C10 C20 120.13(17)
C12 C11 C17 120.69(17)
C12 C11 S1 119.71(14)
C17 C11 S1 119.61(14)
C11 C12 C14 118.91(18)
C18 C13 N7 123.44(16)
C18 C13 C7 121.22(17)
N7 C13 C7 115.28(15)
C19 C14 C12 121.36(18)
C16 C15 C9 120.12(17)
C8 C16 C15 120.10(17)
C21 C17 C11 119.61(18)
N6 C18 C13 130.98(18)
C14 C19 C21 118.77(17)
C14 C19 C24 120.23(18)
C21 C19 C24 121.01(19)
C8 C20 C10 120.17(18)
C17 C21 C19 120.65(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O5 1.4394(14)
S1 O4 1.4397(14)
S1 N7 1.6405(16)
S1 C11 1.7663(18)
O2 C7 1.242(2)
N7 C13 1.442(2)
N6 C18 1.333(2)
N6 C23 1.462(3)
N6 C22 1.465(3)
C7 C13 1.449(2)
C7 C9 1.505(2)
C8 C20 1.386(3)
C8 C16 1.388(3)
C9 C10 1.393(3)
C9 C15 1.395(2)
C10 C20 1.394(3)
C11 C12 1.389(3)
C11 C17 1.391(3)
C12 C14 1.393(3)
C13 C18 1.376(3)
C14 C19 1.391(3)
C15 C16 1.394(3)
C17 C21 1.390(3)
C19 C21 1.395(3)
C19 C24 1.511(3)
