#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/86/4118638.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_4118638
loop_
_publ_author_name
'José A. Souto'
'Peter Becker'
'Álvaro Iglesias'
'Kilian Muñiz'
_publ_section_title
;
 Metal-Free Iodine(III)-Promoted Direct Intermolecular C-H Amination
 Reactions of Acetylenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15505
_journal_page_last               15511
_journal_paper_doi               10.1021/ja306211q
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C29 H24 N2 O5 S2'
_chemical_formula_weight         544.62
_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                 91.546(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.984(4)
_cell_length_b                   15.221(4)
_cell_length_c                   15.456(5)
_cell_measurement_reflns_used    5511
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.16
_cell_measurement_theta_min      2.13
_cell_volume                     2583.1(14)
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support whith MicroMount'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            273086
_diffrn_reflns_theta_full        30.57
_diffrn_reflns_theta_max         30.57
_diffrn_reflns_theta_min         1.85
_diffrn_source                   'Micorfocus source E025 IuS'
_diffrn_source_current           0.6
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.9635
_exptl_absorpt_correction_T_min  0.9517
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         8290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0436
_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)+(0.0541P)²+1.4628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1196
_reflns_number_gt                6737
_reflns_number_total             8290
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja306211q_si_002.cif
_cod_data_source_block           mo_js1137_05
_cod_original_cell_volume        2583.2(14)
_cod_database_code               4118638
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 0.79005(3) 0.11958(2) 0.13973(2) 0.02332(9) Uani 1 1 d .
S2 S 0.81032(3) -0.07001(3) 0.10708(2) 0.02430(9) Uani 1 1 d .
N1 N 0.87494(10) 0.02748(9) 0.13024(8) 0.0235(2) Uani 1 1 d .
N2 N 1.13187(11) 0.10266(9) 0.38607(9) 0.0266(3) Uani 1 1 d .
O1 O 0.68631(9) 0.09783(8) 0.18964(7) 0.0273(2) Uani 1 1 d .
O2 O 0.87499(10) 0.18452(8) 0.17026(8) 0.0287(2) Uani 1 1 d .
O3 O 0.69508(9) -0.05117(8) 0.06542(7) 0.0275(2) Uani 1 1 d .
O4 O 0.90147(11) -0.11830(8) 0.06253(8) 0.0354(3) Uani 1 1 d .
O5 O 0.97912(9) 0.04763(8) 0.29065(7) 0.0248(2) Uani 1 1 d .
C1 C 1.00432(12) 0.03087(10) 0.14271(10) 0.0234(3) Uani 1 1 d .
H1 H 1.0549 0.0247 0.0942 0.028 Uiso 1 1 calc R
C2 C 1.05567(12) 0.04252(10) 0.22140(9) 0.0214(3) Uani 1 1 d .
C3 C 1.18572(12) 0.05350(10) 0.24085(10) 0.0218(3) Uani 1 1 d .
C4 C 1.27576(13) 0.03601(10) 0.18064(10) 0.0239(3) Uani 1 1 d .
H4 H 1.2535 0.0141 0.1248 0.029 Uiso 1 1 calc R
C5 C 1.39723(13) 0.05067(11) 0.20258(10) 0.0270(3) Uani 1 1 d .
H5 H 1.4582 0.0387 0.1618 0.032 Uiso 1 1 calc R
C6 C 1.43020(14) 0.08305(12) 0.28440(11) 0.0310(3) Uani 1 1 d .
H6 H 1.5136 0.0933 0.2989 0.037 Uiso 1 1 calc R
C7 C 1.34219(14) 0.10037(12) 0.34463(11) 0.0314(3) Uani 1 1 d .
H7 H 1.3651 0.1223 0.4003 0.038 Uiso 1 1 calc R
C8 C 1.21913(13) 0.08545(10) 0.32312(10) 0.0248(3) Uani 1 1 d .
C9 C 1.02142(13) 0.08163(10) 0.36805(9) 0.0232(3) Uani 1 1 d .
C10 C 0.92333(13) 0.09017(10) 0.43096(10) 0.0240(3) Uani 1 1 d .
C11 C 0.80197(14) 0.07457(13) 0.40669(11) 0.0314(3) Uani 1 1 d .
H11 H 0.7810 0.0583 0.3489 0.038 Uiso 1 1 calc R
C12 C 0.71155(15) 0.08306(14) 0.46799(11) 0.0366(4) Uani 1 1 d .
H12 H 0.6288 0.0727 0.4517 0.044 Uiso 1 1 calc R
C13 C 0.74181(16) 0.10652(13) 0.55228(11) 0.0346(4) Uani 1 1 d .
H13 H 0.6798 0.1124 0.5936 0.042 Uiso 1 1 calc R
C14 C 0.86253(16) 0.12142(11) 0.57665(10) 0.0296(3) Uani 1 1 d .
H14 H 0.8831 0.1372 0.6347 0.036 Uiso 1 1 calc R
C15 C 0.95352(14) 0.11331(10) 0.51634(10) 0.0267(3) Uani 1 1 d .
H15 H 1.0361 0.1235 0.5332 0.032 Uiso 1 1 calc R
C16 C 0.74054(13) 0.14580(10) 0.03402(10) 0.0241(3) Uani 1 1 d .
C17 C 0.82646(13) 0.17328(11) -0.02510(10) 0.0269(3) Uani 1 1 d .
H17 H 0.9098 0.1791 -0.0080 0.032 Uiso 1 1 calc R
C18 C 0.78809(14) 0.19184(11) -0.10888(11) 0.0294(3) Uani 1 1 d .
H18 H 0.8461 0.2101 -0.1497 0.035 Uiso 1 1 calc R
C19 C 0.66578(15) 0.18432(11) -0.13505(11) 0.0285(3) Uani 1 1 d .
C20 C 0.58120(14) 0.15887(12) -0.07401(11) 0.0306(3) Uani 1 1 d .
H20 H 0.4975 0.1549 -0.0905 0.037 Uiso 1 1 calc R
C21 C 0.61783(13) 0.13931(12) 0.01047(11) 0.0299(3) Uani 1 1 d .
H21 H 0.5599 0.1217 0.0516 0.036 Uiso 1 1 calc R
C22 C 0.62627(18) 0.19918(14) -0.22776(12) 0.0393(4) Uani 1 1 d .
H22A H 0.6911 0.2296 -0.2582 0.059 Uiso 1 1 calc R
H22B H 0.5523 0.2352 -0.2298 0.059 Uiso 1 1 calc R
H22C H 0.6097 0.1425 -0.2557 0.059 Uiso 1 1 calc R
C23 C 0.78605(13) -0.12084(10) 0.20676(10) 0.0241(3) Uani 1 1 d .
C24 C 0.68131(14) -0.10053(11) 0.25129(11) 0.0285(3) Uani 1 1 d .
H24 H 0.6244 -0.0591 0.2282 0.034 Uiso 1 1 calc R
C25 C 0.66101(15) -0.14145(12) 0.32963(11) 0.0312(3) Uani 1 1 d .
H25 H 0.5900 -0.1271 0.3604 0.037 Uiso 1 1 calc R
C26 C 0.74226(16) -0.20305(11) 0.36425(11) 0.0320(3) Uani 1 1 d .
C27 C 0.84678(16) -0.22187(12) 0.31870(13) 0.0374(4) Uani 1 1 d .
H27 H 0.9037 -0.2631 0.3419 0.045 Uiso 1 1 calc R
C28 C 0.86974(14) -0.18174(11) 0.24012(13) 0.0326(3) Uani 1 1 d .
H28 H 0.9412 -0.1955 0.2096 0.039 Uiso 1 1 calc R
C29 C 0.7176(2) -0.24785(13) 0.44861(12) 0.0440(5) Uani 1 1 d .
H29A H 0.7326 -0.3110 0.4430 0.066 Uiso 1 1 calc R
H29B H 0.6326 -0.2381 0.4637 0.066 Uiso 1 1 calc R
H29C H 0.7715 -0.2236 0.4942 0.066 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 S1 O1 120.23(7)
O2 S1 N1 104.18(7)
O1 S1 N1 107.67(7)
O2 S1 C16 109.46(7)
O1 S1 C16 108.86(7)
N1 S1 C16 105.39(7)
O4 S2 O3 120.43(8)
O4 S2 N1 105.00(7)
O3 S2 N1 106.38(7)
O4 S2 C23 108.73(8)
O3 S2 C23 109.27(7)
N1 S2 C23 106.05(7)
C1 N1 S2 118.26(10)
C1 N1 S1 120.42(10)
S2 N1 S1 121.32(7)
C9 N2 C8 117.55(13)
C9 O5 C2 119.86(11)
C2 C1 N1 121.34(12)
C1 C2 O5 117.47(12)
C1 C2 C3 125.99(12)
O5 C2 C3 116.51(13)
C8 C3 C4 119.76(13)
C8 C3 C2 117.20(12)
C4 C3 C2 123.02(13)
C5 C4 C3 119.92(14)
C4 C5 C6 120.21(14)
C7 C6 C5 120.49(14)
C6 C7 C8 119.71(15)
C3 C8 C7 119.92(14)
C3 C8 N2 121.67(13)
C7 C8 N2 118.41(14)
N2 C9 O5 125.53(13)
N2 C9 C10 122.67(14)
O5 C9 C10 111.79(12)
C11 C10 C15 119.84(14)
C11 C10 C9 121.11(14)
C15 C10 C9 119.04(14)
C10 C11 C12 119.56(15)
C13 C12 C11 120.38(16)
C12 C13 C14 120.12(15)
C13 C14 C15 120.16(15)
C14 C15 C10 119.94(15)
C21 C16 C17 121.19(15)
C21 C16 S1 120.12(11)
C17 C16 S1 118.69(11)
C18 C17 C16 118.75(14)
C17 C18 C19 121.45(14)
C20 C19 C18 118.63(15)
C20 C19 C22 120.37(15)
C18 C19 C22 120.95(15)
C21 C20 C19 120.91(14)
C20 C21 C16 119.04(14)
C24 C23 C28 120.70(15)
C24 C23 S2 118.99(12)
C28 C23 S2 120.30(12)
C25 C24 C23 119.16(15)
C24 C25 C26 121.50(16)
C25 C26 C27 118.24(16)
C25 C26 C29 120.71(18)
C27 C26 C29 121.05(17)
C28 C27 C26 121.56(16)
C27 C28 C23 118.83(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4305(12)
S1 O1 1.4320(11)
S1 N1 1.6923(14)
S1 C16 1.7541(17)
S2 O4 1.4333(12)
S2 O3 1.4336(12)
S2 N1 1.6793(14)
S2 C23 1.7509(17)
N1 C1 1.4299(18)
N2 C9 1.2781(19)
N2 C8 1.4087(18)
O5 C9 1.3730(18)
O5 C2 1.3810(16)
C1 C2 1.339(2)
C2 C3 1.4615(19)
C3 C8 1.401(2)
C3 C4 1.4017(19)
C4 C5 1.386(2)
C5 C6 1.396(2)
C6 C7 1.385(2)
C7 C8 1.402(2)
C9 C10 1.476(2)
C10 C11 1.395(2)
C10 C15 1.397(2)
C11 C12 1.397(2)
C12 C13 1.383(3)
C13 C14 1.387(3)
C14 C15 1.390(2)
C16 C21 1.390(2)
C16 C17 1.3954(19)
C17 C18 1.380(2)
C18 C19 1.397(2)
C19 C20 1.397(2)
C19 C22 1.503(2)
C20 C21 1.388(2)
C23 C24 1.391(2)
C23 C28 1.394(2)
C24 C25 1.385(2)
C25 C26 1.391(2)
C26 C27 1.393(3)
C26 C29 1.502(3)
C27 C28 1.389(3)
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
O4 S2 N1 C1 -29.03(13)
O3 S2 N1 C1 -157.74(11)
C23 S2 N1 C1 86.00(12)
O4 S2 N1 S1 151.57(9)
O3 S2 N1 S1 22.86(11)
C23 S2 N1 S1 -93.40(10)
O2 S1 N1 C1 -6.63(13)
O1 S1 N1 C1 -135.35(12)
C16 S1 N1 C1 108.58(12)
O2 S1 N1 S2 172.76(8)
O1 S1 N1 S2 44.04(11)
C16 S1 N1 S2 -72.03(10)
S2 N1 C1 C2 -107.78(15)
S1 N1 C1 C2 71.62(18)
N1 C1 C2 O5 2.5(2)
N1 C1 C2 C3 -175.18(14)
C9 O5 C2 C1 -163.14(14)
C9 O5 C2 C3 14.8(2)
C1 C2 C3 C8 165.16(15)
O5 C2 C3 C8 -12.6(2)
C1 C2 C3 C4 -13.0(2)
O5 C2 C3 C4 169.31(14)
C8 C3 C4 C5 -0.2(2)
C2 C3 C4 C5 177.85(14)
C3 C4 C5 C6 -0.2(2)
C4 C5 C6 C7 0.4(3)
C5 C6 C7 C8 -0.2(3)
C4 C3 C8 C7 0.4(2)
C2 C3 C8 C7 -177.74(15)
C4 C3 C8 N2 -179.03(14)
C2 C3 C8 N2 2.8(2)
C6 C7 C8 C3 -0.3(3)
C6 C7 C8 N2 179.24(16)
C9 N2 C8 C3 5.4(2)
C9 N2 C8 C7 -174.13(16)
C8 N2 C9 O5 -3.5(2)
C8 N2 C9 C10 175.31(14)
C2 O5 C9 N2 -7.0(2)
C2 O5 C9 C10 174.05(13)
N2 C9 C10 C11 173.84(16)
O5 C9 C10 C11 -7.2(2)
N2 C9 C10 C15 -6.9(2)
O5 C9 C10 C15 172.06(14)
C15 C10 C11 C12 0.6(3)
C9 C10 C11 C12 179.84(16)
C10 C11 C12 C13 -0.2(3)
C11 C12 C13 C14 -0.3(3)
C12 C13 C14 C15 0.3(3)
C13 C14 C15 C10 0.1(2)
C11 C10 C15 C14 -0.5(2)
C9 C10 C15 C14 -179.80(14)
O2 S1 C16 C21 -136.08(13)
O1 S1 C16 C21 -2.85(16)
N1 S1 C16 C21 112.41(14)
O2 S1 C16 C17 43.73(14)
O1 S1 C16 C17 176.96(12)
N1 S1 C16 C17 -67.78(14)
C21 C16 C17 C18 -1.8(2)
S1 C16 C17 C18 178.41(12)
C16 C17 C18 C19 0.5(2)
C17 C18 C19 C20 1.1(2)
C17 C18 C19 C22 -176.11(17)
C18 C19 C20 C21 -1.5(3)
C22 C19 C20 C21 175.70(17)
C19 C20 C21 C16 0.3(3)
C17 C16 C21 C20 1.4(3)
S1 C16 C21 C20 -178.83(13)
O4 S2 C23 C24 -163.37(12)
O3 S2 C23 C24 -30.13(15)
N1 S2 C23 C24 84.17(14)
O4 S2 C23 C28 15.64(15)
O3 S2 C23 C28 148.89(13)
N1 S2 C23 C28 -96.81(14)
C28 C23 C24 C25 0.2(2)
S2 C23 C24 C25 179.18(13)
C23 C24 C25 C26 -0.7(3)
C24 C25 C26 C27 1.1(3)
C24 C25 C26 C29 -178.96(17)
C25 C26 C27 C28 -0.9(3)
C29 C26 C27 C28 179.13(17)
C26 C27 C28 C23 0.4(3)
C24 C23 C28 C27 0.0(2)
S2 C23 C28 C27 -179.01(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660658
