#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/77/1507729.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_1507729
loop_
_publ_author_name
'Huang, Ping'
'Chen, Zhiyuan'
'Yang, Qin'
'Peng, Yiyuan'
_publ_section_title
;
 Silver Triflate and Palladium Acetate Co-catalyzed Reaction of
 N'-(2-Alkynylbenzylidene)hydrazide with N-Allyl Ynamide.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2790
_journal_page_last               2793
_journal_paper_doi               10.1021/ol301023m
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C34 H31 N3 O3 S'
_chemical_formula_weight         561.68
_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                 99.406(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.193(4)
_cell_length_b                   19.516(7)
_cell_length_c                   15.403(5)
_cell_measurement_reflns_used    889
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.6652
_cell_measurement_theta_min      2.2385
_cell_volume                     3022.9(19)
_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      293(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  0.1033
_diffrn_reflns_av_sigmaI/netI    0.0812
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14417
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.9729
_exptl_absorpt_correction_T_min  0.9701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         1.174
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       0.027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         5280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0877
_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)+(0.1908P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2214
_refine_ls_wR_factor_ref         0.2586
_reflns_number_gt                3272
_reflns_number_total             5280
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301023m_si_002.cif
_cod_data_source_block           a20321b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3023.0(18)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1507729
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 0.38506(10) 0.24416(5) 0.08682(7) 0.0732(4) Uani 1 1 d .
O1 O 0.3503(3) 0.28646(14) 0.01088(17) 0.0834(8) Uani 1 1 d .
O2 O 0.4121(3) 0.17329(14) 0.0764(2) 0.1035(10) Uani 1 1 d .
N1 N 0.2357(2) 0.36149(12) 0.18920(17) 0.0561(7) Uani 1 1 d .
N2 N 0.2596(3) 0.24738(12) 0.14111(18) 0.0614(7) Uani 1 1 d .
N3 N 0.1418(2) 0.41064(12) 0.16995(16) 0.0518(6) Uani 1 1 d .
C1 C 0.3960(4) 0.47781(18) 0.2652(3) 0.0742(10) Uani 1 1 d .
H1 H 0.4109 0.4527 0.2165 0.089 Uiso 1 1 calc R
C2 C 0.5034(4) 0.5009(2) 0.3248(3) 0.0888(12) Uani 1 1 d .
H2 H 0.5895 0.4920 0.3152 0.107 Uiso 1 1 calc R
C3 C 0.4837(6) 0.5366(2) 0.3972(3) 0.0955(14) Uani 1 1 d .
H3 H 0.5562 0.5514 0.4375 0.115 Uiso 1 1 calc R
C4 C 0.3550(6) 0.5510(2) 0.4111(3) 0.0944(14) Uani 1 1 d .
H4 H 0.3414 0.5758 0.4604 0.113 Uiso 1 1 calc R
C5 C 0.2482(4) 0.52857(18) 0.3518(2) 0.0730(10) Uani 1 1 d .
H5 H 0.1623 0.5381 0.3614 0.088 Uiso 1 1 calc R
C6 C 0.2673(3) 0.49134(16) 0.2768(2) 0.0605(8) Uani 1 1 d .
C7 C 0.1511(3) 0.47477(15) 0.2110(2) 0.0572(8) Uani 1 1 d .
C8 C 0.0484(3) 0.51832(16) 0.1853(2) 0.0655(9) Uani 1 1 d .
H8 H 0.0508 0.5610 0.2124 0.079 Uiso 1 1 calc R
C9 C -0.0615(3) 0.50299(17) 0.1202(2) 0.0638(9) Uani 1 1 d .
C10 C -0.1616(4) 0.5509(2) 0.0915(3) 0.0828(11) Uani 1 1 d .
H10 H -0.1586 0.5934 0.1190 0.099 Uiso 1 1 calc R
C11 C -0.2626(5) 0.5372(2) 0.0248(3) 0.0918(13) Uani 1 1 d .
H11 H -0.3279 0.5698 0.0066 0.110 Uiso 1 1 calc R
C12 C -0.2666(4) 0.4739(2) -0.0155(3) 0.0883(12) Uani 1 1 d .
H12 H -0.3350 0.4644 -0.0617 0.106 Uiso 1 1 calc R
C13 C -0.1739(4) 0.42502(19) 0.0102(2) 0.0703(9) Uani 1 1 d .
H13 H -0.1798 0.3827 -0.0179 0.084 Uiso 1 1 calc R
C14 C -0.0692(3) 0.43827(16) 0.0791(2) 0.0580(8) Uani 1 1 d .
C15 C 0.0352(3) 0.38948(15) 0.10873(19) 0.0524(7) Uani 1 1 d .
C16 C 0.0634(3) 0.32186(15) 0.08784(19) 0.0548(8) Uani 1 1 d .
C17 C -0.0215(3) 0.27053(16) 0.0335(2) 0.0590(8) Uani 1 1 d .
C18 C -0.1441(4) 0.25273(18) 0.0538(2) 0.0715(10) Uani 1 1 d .
H18 H -0.1755 0.2746 0.1000 0.086 Uiso 1 1 calc R
C19 C -0.2206(4) 0.2026(2) 0.0063(3) 0.0857(12) Uani 1 1 d .
H19 H -0.3035 0.1914 0.0200 0.103 Uiso 1 1 calc R
C20 C -0.1735(5) 0.1691(2) -0.0620(3) 0.0847(12) Uani 1 1 d .
H20 H -0.2239 0.1349 -0.0937 0.102 Uiso 1 1 calc R
C21 C -0.0543(5) 0.1865(2) -0.0817(3) 0.0824(11) Uani 1 1 d .
H21 H -0.0230 0.1641 -0.1275 0.099 Uiso 1 1 calc R
C22 C 0.0235(4) 0.23732(18) -0.0352(2) 0.0691(9) Uani 1 1 d .
H22 H 0.1053 0.2488 -0.0503 0.083 Uiso 1 1 calc R
C23 C 0.1876(3) 0.30948(15) 0.1385(2) 0.0531(7) Uani 1 1 d .
C24 C 0.2698(4) 0.20644(19) 0.2244(3) 0.0798(11) Uani 1 1 d .
H24A H 0.3254 0.1666 0.2201 0.096 Uiso 1 1 calc R
H24B H 0.3123 0.2341 0.2734 0.096 Uiso 1 1 calc R
C25 C 0.1395(5) 0.1840(2) 0.2415(3) 0.0910(12) Uani 1 1 d .
H25 H 0.0772 0.1721 0.1928 0.109 Uiso 1 1 calc R
C26 C 0.1030(6) 0.1790(3) 0.3163(4) 0.1162(17) Uani 1 1 d .
H26 H 0.1633 0.1944 0.3642 0.139 Uiso 1 1 calc R
C27 C -0.0238(7) 0.1517(4) 0.3360(5) 0.166(3) Uani 1 1 d .
H27A H -0.0881 0.1505 0.2830 0.250 Uiso 1 1 calc R
H27B H -0.0558 0.1807 0.3784 0.250 Uiso 1 1 calc R
H27C H -0.0101 0.1062 0.3594 0.250 Uiso 1 1 calc R
C28 C 0.5236(3) 0.27981(19) 0.1535(2) 0.0670(9) Uani 1 1 d .
C29 C 0.5969(4) 0.2428(2) 0.2191(3) 0.0896(13) Uani 1 1 d .
H29 H 0.5745 0.1975 0.2279 0.108 Uiso 1 1 calc R
C30 C 0.7037(5) 0.2718(3) 0.2724(3) 0.1053(16) Uani 1 1 d .
H30 H 0.7498 0.2462 0.3184 0.126 Uiso 1 1 calc R
C31 C 0.7442(4) 0.3374(3) 0.2596(3) 0.0923(14) Uani 1 1 d .
C32 C 0.8662(5) 0.3653(4) 0.3148(4) 0.142(2) Uani 1 1 d .
H32A H 0.9435 0.3483 0.2936 0.213 Uiso 1 1 calc R
H32B H 0.8688 0.3512 0.3748 0.213 Uiso 1 1 calc R
H32C H 0.8649 0.4145 0.3117 0.213 Uiso 1 1 calc R
C33 C 0.6706(4) 0.3754(2) 0.1922(3) 0.0825(11) Uani 1 1 d .
H33 H 0.6956 0.4203 0.1824 0.099 Uiso 1 1 calc R
C34 C 0.5620(4) 0.3476(2) 0.1401(3) 0.0737(10) Uani 1 1 d .
H34 H 0.5134 0.3738 0.0956 0.088 Uiso 1 1 calc R
O3 O 0.0319(5) 0.47204(19) 0.5082(3) 0.0757(15) Uani 0.50 1 d P
H3A H 0.0452 0.4291 0.5117 0.091 Uiso 0.50 1 d PR
H3B H 0.1068 0.4918 0.5219 0.091 Uiso 0.50 1 d PR
O4 O 0.8568(4) 0.5487(2) 0.3692(4) 0.0783(15) Uani 0.50 1 d P
H4A H 0.9228 0.5220 0.3694 0.094 Uiso 0.50 1 d PR
H4B H 0.8381 0.5660 0.3180 0.094 Uiso 0.50 1 d PR
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
_geom_angle_site_symmetry_1
O2 S1 O1 119.68(19) .
O2 S1 N2 106.05(16) .
O1 S1 N2 106.61(15) .
O2 S1 C28 107.46(18) .
O1 S1 C28 108.62(17) .
N2 S1 C28 107.92(15) .
C23 N1 N3 103.5(2) .
C23 N2 C24 116.4(3) .
C23 N2 S1 117.6(2) .
C24 N2 S1 117.7(2) .
N1 N3 C15 112.8(2) .
N1 N3 C7 122.8(3) .
C15 N3 C7 124.3(3) .
C6 C1 C2 121.2(4) .
C6 C1 H1 119.4 .
C2 C1 H1 119.4 .
C3 C2 C1 120.3(4) .
C3 C2 H2 119.8 .
C1 C2 H2 119.8 .
C2 C3 C4 120.0(4) .
C2 C3 H3 120.0 .
C4 C3 H3 120.0 .
C5 C4 C3 119.8(4) .
C5 C4 H4 120.1 .
C3 C4 H4 120.1 .
C4 C5 C6 120.7(4) .
C4 C5 H5 119.7 .
C6 C5 H5 119.7 .
C1 C6 C5 118.0(3) .
C1 C6 C7 123.2(3) .
C5 C6 C7 118.6(3) .
C8 C7 N3 115.9(3) .
C8 C7 C6 124.2(3) .
N3 C7 C6 119.9(3) .
C7 C8 C9 124.1(3) .
C7 C8 H8 117.9 .
C9 C8 H8 117.9 .
C10 C9 C8 122.5(3) .
C10 C9 C14 118.2(3) .
C8 C9 C14 119.3(3) .
C11 C10 C9 122.1(4) .
C11 C10 H10 119.0 .
C9 C10 H10 119.0 .
C10 C11 C12 118.6(4) .
C10 C11 H11 120.7 .
C12 C11 H11 120.7 .
C13 C12 C11 122.1(4) .
C13 C12 H12 119.0 .
C11 C12 H12 119.0 .
C12 C13 C14 120.0(4) .
C12 C13 H13 120.0 .
C14 C13 H13 120.0 .
C13 C14 C9 119.0(3) .
C13 C14 C15 123.2(3) .
C9 C14 C15 117.7(3) .
N3 C15 C16 105.7(3) .
N3 C15 C14 118.4(3) .
C16 C15 C14 135.8(3) .
C23 C16 C15 103.7(3) .
C23 C16 C17 126.1(3) .
C15 C16 C17 129.9(3) .
C22 C17 C18 118.7(3) .
C22 C17 C16 120.7(3) .
C18 C17 C16 120.4(3) .
C17 C18 C19 120.7(3) .
C17 C18 H18 119.7 .
C19 C18 H18 119.7 .
C18 C19 C20 120.0(4) .
C18 C19 H19 120.0 .
C20 C19 H19 120.0 .
C21 C20 C19 119.2(3) .
C21 C20 H20 120.4 .
C19 C20 H20 120.4 .
C20 C21 C22 121.6(4) .
C20 C21 H21 119.2 .
C22 C21 H21 119.2 .
C17 C22 C21 119.7(4) .
C17 C22 H22 120.1 .
C21 C22 H22 120.1 .
N1 C23 C16 114.3(3) .
N1 C23 N2 120.0(3) .
C16 C23 N2 125.7(3) .
C25 C24 N2 112.1(3) .
C25 C24 H24A 109.2 .
N2 C24 H24A 109.2 .
C25 C24 H24B 109.2 .
N2 C24 H24B 109.2 .
H24A C24 H24B 107.9 .
C26 C25 C24 126.5(5) .
C26 C25 H25 116.7 .
C24 C25 H25 116.7 .
C25 C26 C27 127.6(6) .
C25 C26 H26 116.2 .
C27 C26 H26 116.2 .
C26 C27 H27A 109.5 .
C26 C27 H27B 109.5 .
H27A C27 H27B 109.5 .
C26 C27 H27C 109.5 .
H27A C27 H27C 109.5 .
H27B C27 H27C 109.5 .
C29 C28 C34 118.4(4) .
C29 C28 S1 121.2(3) .
C34 C28 S1 120.4(3) .
C28 C29 C30 120.7(4) .
C28 C29 H29 119.7 .
C30 C29 H29 119.7 .
C31 C30 C29 121.8(4) .
C31 C30 H30 119.1 .
C29 C30 H30 119.1 .
C30 C31 C33 117.9(4) .
C30 C31 C32 120.2(5) .
C33 C31 C32 121.9(6) .
C31 C32 H32A 109.5 .
C31 C32 H32B 109.5 .
H32A C32 H32B 109.5 .
C31 C32 H32C 109.5 .
H32A C32 H32C 109.5 .
H32B C32 H32C 109.5 .
C34 C33 C31 120.7(4) .
C34 C33 H33 119.6 .
C31 C33 H33 119.6 .
C33 C34 C28 120.4(4) .
C33 C34 H34 119.8 .
C28 C34 H34 119.8 .
O3 O3 H3A 158.2 3_566
O3 O3 H3B 94.0 3_566
H3A O3 H3B 107.7 .
H4A O4 H4B 107.7 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.425(3) .
S1 O1 1.428(3) .
S1 N2 1.640(3) .
S1 C28 1.749(4) .
N1 C23 1.325(4) .
N1 N3 1.353(3) .
N2 C23 1.414(4) .
N2 C24 1.500(5) .
N3 C15 1.380(4) .
N3 C7 1.399(4) .
C1 C6 1.378(5) .
C1 C2 1.384(6) .
C1 H1 0.9300 .
C2 C3 1.356(7) .
C2 H2 0.9300 .
C3 C4 1.393(7) .
C3 H3 0.9300 .
C4 C5 1.374(6) .
C4 H4 0.9300 .
C5 C6 1.404(5) .
C5 H5 0.9300 .
C6 C7 1.464(5) .
C7 C8 1.356(5) .
C8 C9 1.409(5) .
C8 H8 0.9300 .
C9 C10 1.400(5) .
C9 C14 1.409(5) .
C10 C11 1.357(6) .
C10 H10 0.9300 .
C11 C12 1.380(6) .
C11 H11 0.9300 .
C12 C13 1.355(5) .
C12 H12 0.9300 .
C13 C14 1.401(5) .
C13 H13 0.9300 .
C14 C15 1.445(4) .
C15 C16 1.400(4) .
C16 C23 1.395(5) .
C16 C17 1.488(4) .
C17 C22 1.381(5) .
C17 C18 1.382(5) .
C18 C19 1.383(5) .
C18 H18 0.9300 .
C19 C20 1.389(6) .
C19 H19 0.9300 .
C20 C21 1.343(6) .
C20 H20 0.9300 .
C21 C22 1.393(5) .
C21 H21 0.9300 .
C22 H22 0.9300 .
C24 C25 1.463(6) .
C24 H24A 0.9700 .
C24 H24B 0.9700 .
C25 C26 1.271(6) .
C25 H25 0.9300 .
C26 C27 1.475(8) .
C26 H26 0.9300 .
C27 H27A 0.9600 .
C27 H27B 0.9600 .
C27 H27C 0.9600 .
C28 C29 1.362(5) .
C28 C34 1.405(5) .
C29 C30 1.374(7) .
C29 H29 0.9300 .
C30 C31 1.368(7) .
C30 H30 0.9300 .
C31 C33 1.392(6) .
C31 C32 1.491(7) .
C32 H32A 0.9600 .
C32 H32B 0.9600 .
C32 H32C 0.9600 .
C33 C34 1.369(5) .
C33 H33 0.9300 .
C34 H34 0.9300 .
O3 O3 1.275(9) 3_566
O3 H3A 0.8500 .
O3 H3B 0.8500 .
O4 H4A 0.8501 .
O4 H4B 0.8500 .
