#------------------------------------------------------------------------------
#$Date: 2017-02-18 22:30:37 +0200 (Sat, 18 Feb 2017) $
#$Revision: 192273 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/96/7119680.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_7119680
loop_
_publ_author_name
'Kai Sun'
'Xin Wang'
'Yunhe Lv'
'Gang Li'
'Hezhen Jiao'
'Changwei Dai'
'Yangyang Li'
'Chong Zhang'
'Lin Liu'
_publ_section_title
;
 Peroxodisulfate-mediated selenoamination of alkenes yielding
 amidoselenide-containing sulfamides and azoles
;
_journal_name_full               Chem.Commun.
_journal_page_first              8471
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C21 H17 N O3 S Se'
_chemical_formula_weight         442.38
_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
_audit_update_record
;
2016-05-19 deposited with the CCDC.
2016-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                102.367(3)
_cell_angle_beta                 94.393(3)
_cell_angle_gamma                107.218(3)
_cell_formula_units_Z            4
_cell_length_a                   9.7234(4)
_cell_length_b                   9.8305(4)
_cell_length_c                   22.0952(9)
_cell_measurement_reflns_used    6383
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.73
_cell_measurement_theta_min      2.24
_cell_volume                     1948.22(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21294
_diffrn_reflns_theta_full        25.60
_diffrn_reflns_theta_max         25.60
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    2.055
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         7204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0331
_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)+(0.0393P)²+0.5465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0846
_reflns_number_gt                5259
_reflns_number_total             7204
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc04225b2.cif
_cod_data_source_block           1
_cod_original_cell_volume        1948.22(14)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7119680
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
Se1 Se 0.32713(3) 0.80343(3) 0.116142(14) 0.05833(11) Uani 1 1 d . . .
Se2 Se -0.16655(3) 0.57190(4) 0.446373(15) 0.06436(11) Uani 1 1 d . . .
S2 S 0.26068(7) 0.65472(7) 0.40434(3) 0.04264(16) Uani 1 1 d . . .
S1 S 0.34069(8) 0.24916(9) 0.07288(4) 0.0573(2) Uani 1 1 d . . .
O3 O 0.0293(2) 0.3218(2) -0.00896(9) 0.0634(5) Uani 1 1 d . . .
O4 O 0.1763(2) 0.50541(19) 0.39683(9) 0.0603(5) Uani 1 1 d . . .
C23 C 0.3433(3) 0.8398(3) 0.51134(12) 0.0438(6) Uani 1 1 d . . .
C31 C 0.0701(3) 0.8797(3) 0.34782(12) 0.0399(6) Uani 1 1 d . . .
O5 O 0.3313(2) 0.6913(2) 0.35345(9) 0.0623(5) Uani 1 1 d . . .
O6 O 0.1590(2) 0.9555(2) 0.50489(9) 0.0658(6) Uani 1 1 d . . .
C30 C 0.0338(3) 0.7549(3) 0.38060(11) 0.0405(6) Uani 1 1 d . . .
H30A H 0.0129 0.6635 0.3480 0.049 Uiso 1 1 calc R . .
C22 C 0.2125(3) 0.8642(3) 0.48281(12) 0.0449(6) Uani 1 1 d . . .
C16 C 0.4886(3) 0.7973(3) 0.16953(13) 0.0476(7) Uani 1 1 d . . .
N1 N 0.2282(2) 0.3427(2) 0.05952(10) 0.0482(5) Uani 1 1 d . . .
C21 C 0.4749(3) 0.7836(3) 0.22961(13) 0.0537(7) Uani 1 1 d . . .
H21A H 0.3873 0.7788 0.2447 0.064 Uiso 1 1 calc R . .
C8 C 0.2481(3) 0.4892(3) 0.10187(11) 0.0451(6) Uani 1 1 d . . .
H8A H 0.3376 0.5133 0.1312 0.054 Uiso 1 1 calc R . .
C2 C 0.1427(3) 0.1335(3) -0.02330(12) 0.0498(7) Uani 1 1 d . . .
C290 C -0.1026(3) 0.7425(3) 0.41202(14) 0.0525(7) Uani 1 1 d . . .
H29A H -0.1813 0.7397 0.3815 0.063 Uiso 1 1 calc R . .
H29B H -0.0839 0.8304 0.4456 0.063 Uiso 1 1 calc R . .
C9 C 0.2764(3) 0.6043(3) 0.06372(12) 0.0505(7) Uani 1 1 d . . .
H9A H 0.1900 0.5846 0.0339 0.061 Uiso 1 1 calc R . .
H9B H 0.3552 0.5965 0.0402 0.061 Uiso 1 1 calc R . .
N2 N 0.1607(2) 0.7640(2) 0.42512(9) 0.0389(5) Uani 1 1 d . . .
C24 C 0.4272(3) 0.9173(3) 0.56884(13) 0.0590(8) Uani 1 1 d . . .
H24A H 0.4049 0.9941 0.5942 0.071 Uiso 1 1 calc R . .
C13 C -0.0949(4) 0.4575(3) 0.21407(15) 0.0675(9) Uani 1 1 d . . .
H13A H -0.1696 0.4483 0.2383 0.081 Uiso 1 1 calc R . .
C1 C 0.1221(3) 0.2728(3) 0.00757(12) 0.0478(7) Uani 1 1 d . . .
C37 C -0.2636(3) 0.4278(3) 0.37005(15) 0.0580(8) Uani 1 1 d . . .
C29 C 0.4976(3) 0.6874(3) 0.49250(15) 0.0597(8) Uani 1 1 d . . .
H29C H 0.5204 0.6112 0.4670 0.072 Uiso 1 1 calc R . .
C36 C 0.1159(3) 0.8564(3) 0.28987(13) 0.0484(7) Uani 1 1 d . . .
H36A H 0.1254 0.7657 0.2719 0.058 Uiso 1 1 calc R . .
C14 C 0.0303(4) 0.4358(3) 0.23430(14) 0.0658(9) Uani 1 1 d . . .
H14A H 0.0413 0.4121 0.2725 0.079 Uiso 1 1 calc R . .
C28 C 0.3799(3) 0.7281(3) 0.47472(12) 0.0424(6) Uani 1 1 d . . .
C32 C 0.0549(3) 1.0149(3) 0.37349(14) 0.0533(7) Uani 1 1 d . . .
H32A H 0.0229 1.0319 0.4121 0.064 Uiso 1 1 calc R . .
C7 C 0.2571(3) 0.1053(3) 0.00718(13) 0.0532(7) Uani 1 1 d . . .
C10 C 0.1268(3) 0.4825(3) 0.14080(12) 0.0450(6) Uani 1 1 d . . .
O2 O 0.3182(3) 0.2050(3) 0.12958(10) 0.0818(7) Uani 1 1 d . . .
C20 C 0.5900(4) 0.7770(4) 0.26733(14) 0.0655(9) Uani 1 1 d . . .
H20A H 0.5804 0.7684 0.3080 0.079 Uiso 1 1 calc R . .
C11 C -0.0013(3) 0.5055(3) 0.12106(14) 0.0562(7) Uani 1 1 d . . .
H11A H -0.0132 0.5297 0.0830 0.067 Uiso 1 1 calc R . .
C15 C 0.1415(3) 0.4487(3) 0.19847(12) 0.0536(7) Uani 1 1 d . . .
H15A H 0.2273 0.4346 0.2130 0.064 Uiso 1 1 calc R . .
C17 C 0.6191(3) 0.8046(4) 0.14816(15) 0.0673(9) Uani 1 1 d . . .
H17A H 0.6298 0.8146 0.1077 0.081 Uiso 1 1 calc R . .
C12 C -0.1113(4) 0.4929(3) 0.15760(16) 0.0664(9) Uani 1 1 d . . .
H12A H -0.1970 0.5085 0.1439 0.080 Uiso 1 1 calc R . .
C25 C 0.5458(3) 0.8764(4) 0.58728(15) 0.0679(9) Uani 1 1 d . . .
H25A H 0.6032 0.9260 0.6259 0.081 Uiso 1 1 calc R . .
C42 C -0.2184(4) 0.3078(4) 0.3500(2) 0.0834(11) Uani 1 1 d . . .
H42A H -0.1380 0.2988 0.3724 0.100 Uiso 1 1 calc R . .
O1 O 0.4843(2) 0.3290(3) 0.06632(12) 0.0867(7) Uani 1 1 d . . .
C38 C -0.3838(4) 0.4389(4) 0.33599(17) 0.0718(9) Uani 1 1 d . . .
H38A H -0.4168 0.5185 0.3490 0.086 Uiso 1 1 calc R . .
C26 C 0.5799(3) 0.7644(4) 0.54967(16) 0.0714(9) Uani 1 1 d . . .
H26A H 0.6604 0.7401 0.5632 0.086 Uiso 1 1 calc R . .
C33 C 0.0874(3) 1.1250(3) 0.34164(18) 0.0659(9) Uani 1 1 d . . .
H33A H 0.0776 1.2158 0.3592 0.079 Uiso 1 1 calc R . .
C6 C 0.2951(4) -0.0184(3) -0.01448(17) 0.0709(9) Uani 1 1 d . . .
H6A H 0.3715 -0.0362 0.0069 0.085 Uiso 1 1 calc R . .
C34 C 0.1338(3) 1.1010(4) 0.28464(19) 0.0705(9) Uani 1 1 d . . .
H34A H 0.1560 1.1756 0.2637 0.085 Uiso 1 1 calc R . .
C3 C 0.0623(4) 0.0333(4) -0.07795(14) 0.0686(9) Uani 1 1 d . . .
H3A H -0.0162 0.0488 -0.0989 0.082 Uiso 1 1 calc R . .
C35 C 0.1477(3) 0.9670(4) 0.25829(15) 0.0637(8) Uani 1 1 d . . .
H35A H 0.1783 0.9503 0.2193 0.076 Uiso 1 1 calc R . .
C19 C 0.7194(4) 0.7830(4) 0.24539(17) 0.0760(10) Uani 1 1 d . . .
H19A H 0.7971 0.7775 0.2710 0.091 Uiso 1 1 calc R . .
C4 C 0.1017(5) -0.0898(4) -0.10041(18) 0.0864(12) Uani 1 1 d . . .
H4B H 0.0502 -0.1569 -0.1374 0.104 Uiso 1 1 calc R . .
C5 C 0.2152(5) -0.1149(4) -0.0692(2) 0.0921(13) Uani 1 1 d . . .
H5B H 0.2389 -0.1990 -0.0854 0.111 Uiso 1 1 calc R . .
C39 C -0.4543(5) 0.3304(5) 0.2824(2) 0.0967(13) Uani 1 1 d . . .
H39A H -0.5342 0.3382 0.2592 0.116 Uiso 1 1 calc R . .
C18 C 0.7337(4) 0.7971(4) 0.18609(18) 0.0814(11) Uani 1 1 d . . .
H18A H 0.8214 0.8017 0.1712 0.098 Uiso 1 1 calc R . .
C41 C -0.2923(7) 0.2007(5) 0.2964(3) 0.1154(18) Uani 1 1 d . . .
H41A H -0.2617 0.1195 0.2831 0.138 Uiso 1 1 calc R . .
C40 C -0.4086(7) 0.2131(6) 0.2634(3) 0.1210(18) Uani 1 1 d . . .
H40A H -0.4575 0.1408 0.2274 0.145 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'
Se Se -0.0929 2.2259 '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
C16 Se1 C9 97.06(11) . .
C37 Se2 C290 98.51(12) . .
O5 S2 O4 117.25(13) . .
O5 S2 N2 109.68(11) . .
O4 S2 N2 110.17(11) . .
O5 S2 C28 111.18(13) . .
O4 S2 C28 112.90(12) . .
N2 S2 C28 93.01(11) . .
O1 S1 O2 118.30(15) . .
O1 S1 N1 109.48(13) . .
O2 S1 N1 109.27(13) . .
O1 S1 C7 111.73(15) . .
O2 S1 C7 111.93(14) . .
N1 S1 C7 93.21(13) . .
C28 C23 C24 119.8(3) . .
C28 C23 C22 113.6(2) . .
C24 C23 C22 126.6(3) . .
C36 C31 C32 118.8(2) . .
C36 C31 C30 119.2(2) . .
C32 C31 C30 122.0(2) . .
N2 C30 C31 111.46(19) . .
N2 C30 C290 111.6(2) . .
C31 C30 C290 113.3(2) . .
O6 C22 N2 124.7(2) . .
O6 C22 C23 126.7(2) . .
N2 C22 C23 108.6(2) . .
C21 C16 C17 119.1(3) . .
C21 C16 Se1 120.3(2) . .
C17 C16 Se1 120.6(2) . .
C1 N1 C8 125.7(2) . .
C1 N1 S1 114.44(19) . .
C8 N1 S1 119.89(16) . .
C20 C21 C16 120.2(3) . .
N1 C8 C10 111.1(2) . .
N1 C8 C9 109.0(2) . .
C10 C8 C9 116.9(2) . .
C7 C2 C3 119.2(3) . .
C7 C2 C1 113.6(2) . .
C3 C2 C1 127.2(3) . .
C30 C290 Se2 114.99(18) . .
C8 C9 Se1 112.38(17) . .
C22 N2 C30 125.6(2) . .
C22 N2 S2 114.65(16) . .
C30 N2 S2 119.58(15) . .
C23 C24 C25 117.7(3) . .
C14 C13 C12 119.9(3) . .
O3 C1 N1 124.1(3) . .
O3 C1 C2 126.8(2) . .
N1 C1 C2 109.1(2) . .
C42 C37 C38 119.0(3) . .
C42 C37 Se2 120.0(3) . .
C38 C37 Se2 120.9(3) . .
C26 C29 C28 117.0(3) . .
C31 C36 C35 120.7(3) . .
C13 C14 C15 120.4(3) . .
C23 C28 C29 122.9(2) . .
C23 C28 S2 110.04(18) . .
C29 C28 S2 127.0(2) . .
C31 C32 C33 120.1(3) . .
C6 C7 C2 122.6(3) . .
C6 C7 S1 127.8(3) . .
C2 C7 S1 109.6(2) . .
C11 C10 C15 118.1(3) . .
C11 C10 C8 122.7(2) . .
C15 C10 C8 119.1(2) . .
C21 C20 C19 120.3(3) . .
C12 C11 C10 120.4(3) . .
C14 C15 C10 120.8(3) . .
C18 C17 C16 120.4(3) . .
C13 C12 C11 120.3(3) . .
C26 C25 C24 121.3(3) . .
C37 C42 C41 120.1(4) . .
C39 C38 C37 119.3(4) . .
C25 C26 C29 121.4(3) . .
C34 C33 C32 120.5(3) . .
C7 C6 C5 117.1(4) . .
C33 C34 C35 120.0(3) . .
C4 C3 C2 118.4(3) . .
C34 C35 C36 119.9(3) . .
C18 C19 C20 119.8(3) . .
C5 C4 C3 121.1(4) . .
C4 C5 C6 121.6(4) . .
C40 C39 C38 120.9(5) . .
C19 C18 C17 120.2(3) . .
C40 C41 C42 120.4(5) . .
C41 C40 C39 120.3(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 C16 1.914(3) .
Se1 C9 1.946(3) .
Se2 C37 1.919(3) .
Se2 C290 1.943(3) .
S2 O5 1.4180(19) .
S2 O4 1.4202(19) .
S2 N2 1.669(2) .
S2 C28 1.741(3) .
S1 O1 1.420(2) .
S1 O2 1.423(2) .
S1 N1 1.671(2) .
S1 C7 1.740(3) .
O3 C1 1.210(3) .
C23 C28 1.371(4) .
C23 C24 1.385(4) .
C23 C22 1.482(4) .
C31 C36 1.383(4) .
C31 C32 1.384(4) .
C31 C30 1.522(3) .
O6 C22 1.200(3) .
C30 N2 1.487(3) .
C30 C290 1.528(4) .
C22 N2 1.385(3) .
C16 C21 1.375(4) .
C16 C17 1.375(4) .
N1 C1 1.384(3) .
N1 C8 1.489(3) .
C21 C20 1.369(4) .
C8 C10 1.507(4) .
C8 C9 1.525(3) .
C2 C7 1.383(4) .
C2 C3 1.389(4) .
C2 C1 1.471(4) .
C24 C25 1.390(4) .
C13 C14 1.355(5) .
C13 C12 1.376(4) .
C37 C42 1.377(5) .
C37 C38 1.385(4) .
C29 C26 1.373(4) .
C29 C28 1.377(4) .
C36 C35 1.387(4) .
C14 C15 1.380(4) .
C32 C33 1.388(4) .
C7 C6 1.375(4) .
C10 C11 1.385(4) .
C10 C15 1.391(3) .
C20 C19 1.373(4) .
C11 C12 1.382(4) .
C17 C18 1.371(4) .
C25 C26 1.370(5) .
C42 C41 1.384(6) .
C38 C39 1.382(5) .
C33 C34 1.367(5) .
C6 C5 1.376(5) .
C34 C35 1.372(5) .
C3 C4 1.380(5) .
C19 C18 1.360(5) .
C4 C5 1.368(5) .
C39 C40 1.352(7) .
C41 C40 1.349(7) .
