#------------------------------------------------------------------------------
#$Date: 2019-11-23 22:58:58 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235474 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/69/4036959.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_4036959
loop_
_publ_author_name
'Romero, R Martín'
'Souto, José A'
'Muñiz, Kilian'
_publ_section_title
;
 Substitution Effects of Hypervalent Iodine(III) Reagents in the
 Diamination of Styrene.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6118
_journal_page_last               6122
_journal_paper_doi               10.1021/acs.joc.6b01070
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C22 H24 I N O5 S2'
_chemical_formula_weight         573.46
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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
_cell_angle_alpha                101.3780(10)
_cell_angle_beta                 101.2430(10)
_cell_angle_gamma                109.5590(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4165(2)
_cell_length_b                   10.5253(2)
_cell_length_c                   12.9540(4)
_cell_measurement_reflns_used    7793
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.38
_cell_measurement_theta_min      3.58
_cell_volume                     1137.70(5)
_computing_cell_refinement       'Bruker APEX2 v2009.1-0'
_computing_data_collection       'Bruker APEX2 v2009.1-0'
_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    'SHELXS-97 (Sheldrick, 2008)'
_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 0.968
_diffrn_measured_fraction_theta_max 0.618
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support
'magnetic support whith 10 micron nylon fiber cryoloop'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9595
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         36.40
_diffrn_reflns_theta_min         2.50
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_current           70
_diffrn_source_power             50
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_source_type              'Bruker-Nonius FR 591'
_exptl_absorpt_coefficient_mu    1.625
_exptl_absorpt_correction_T_max  0.9641
_exptl_absorpt_correction_T_min  0.8828
_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            colourless
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.228
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         6860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0231
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0392P)²+0.2501P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0685
_reflns_number_gt                6557
_reflns_number_total             6860
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b01070_si_002.cif
_cod_data_source_block           js275
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_diffrn_measurement_specimen_suppport' was replaced with
'_diffrn_measurement_specimen_support' as specified in the
replacement file
'/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/lists/replacement-tags.lst'.

Automatic conversion script
Id: cif_correct_tags 6909 2019-04-08 15:41:33Z antanas 

The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C22 H24 I1 N1 O5 S2'
_cod_database_code               4036959
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
C1 C 0.71481(17) 0.31862(17) 0.27800(16) 0.0121(3) Uani 1 1 d .
C2 C 0.65039(17) 0.31002(18) 0.16973(18) 0.0149(4) Uani 1 1 d .
H2 H 0.5434 0.2970 0.1440 0.018 Uiso 1 1 calc R
C3 C 0.74595(18) 0.32095(19) 0.09946(18) 0.0156(4) Uani 1 1 d .
H3 H 0.7040 0.3174 0.0256 0.019 Uiso 1 1 calc R
C4 C 0.90251(18) 0.33705(18) 0.13590(18) 0.0158(4) Uani 1 1 d .
C5 C 0.96294(17) 0.34279(18) 0.24505(17) 0.0153(4) Uani 1 1 d .
H5 H 1.0686 0.3520 0.2701 0.018 Uiso 1 1 calc R
C6 C 0.87107(17) 0.33531(18) 0.31790(18) 0.0151(4) Uani 1 1 d .
H6 H 0.9134 0.3414 0.3924 0.018 Uiso 1 1 calc R
C7 C 1.0038(2) 0.3470(2) 0.0588(2) 0.0241(5) Uani 1 1 d .
H7A H 0.9420 0.3394 -0.0140 0.036 Uiso 1 1 calc R
H7B H 1.0417 0.2706 0.0537 0.036 Uiso 1 1 calc R
H7C H 1.0936 0.4376 0.0866 0.036 Uiso 1 1 calc R
C8 C 0.51079(17) 0.66477(17) 0.20249(16) 0.0123(3) Uani 1 1 d .
C9 C 0.49992(19) 0.79562(18) 0.22375(18) 0.0155(4) Uani 1 1 d .
H9 H 0.4474 0.8203 0.2752 0.019 Uiso 1 1 calc R
C10 C 0.5673(2) 0.88960(18) 0.16827(19) 0.0177(4) Uani 1 1 d .
H10 H 0.5604 0.9791 0.1820 0.021 Uiso 1 1 calc R
C11 C 0.64501(19) 0.85414(18) 0.09249(18) 0.0171(4) Uani 1 1 d .
C12 C 0.65291(19) 0.72185(19) 0.07228(18) 0.0165(4) Uani 1 1 d .
H12 H 0.7038 0.6960 0.0201 0.020 Uiso 1 1 calc R
C13 C 0.58697(18) 0.62739(17) 0.12783(17) 0.0136(4) Uani 1 1 d .
H13 H 0.5942 0.5380 0.1146 0.016 Uiso 1 1 calc R
C14 C 0.7215(3) 0.9565(2) 0.0343(2) 0.0271(5) Uani 1 1 d .
H14A H 0.6616 1.0151 0.0225 0.041 Uiso 1 1 calc R
H14B H 0.7237 0.9046 -0.0367 0.041 Uiso 1 1 calc R
H14C H 0.8292 1.0163 0.0791 0.041 Uiso 1 1 calc R
C15 C 0.85251(16) 0.76729(17) 0.37459(17) 0.0133(4) Uani 1 1 d .
C16 C 0.87732(18) 0.90461(18) 0.37322(18) 0.0167(4) Uani 1 1 d .
H16 H 0.8220 0.9529 0.4074 0.020 Uiso 1 1 calc R
C17 C 0.98476(19) 0.97055(19) 0.32088(19) 0.0189(4) Uani 1 1 d .
H17 H 1.0023 1.0645 0.3198 0.023 Uiso 1 1 calc R
C18 C 1.06610(19) 0.9020(2) 0.27069(18) 0.0193(4) Uani 1 1 d .
C19 C 1.03855(19) 0.7627(2) 0.27198(19) 0.0201(4) Uani 1 1 d .
H19 H 1.0927 0.7140 0.2370 0.024 Uiso 1 1 calc R
C20 C 0.93244(19) 0.69582(19) 0.32423(19) 0.0176(4) Uani 1 1 d .
H20 H 0.9147 0.6019 0.3255 0.021 Uiso 1 1 calc R
C21 C 1.1847(2) 0.9752(2) 0.2166(2) 0.0299(5) Uani 1 1 d .
H21A H 1.1785 1.0655 0.2135 0.045 Uiso 1 1 calc R
H21B H 1.1621 0.9162 0.1419 0.045 Uiso 1 1 calc R
H21C H 1.2905 0.9914 0.2591 0.045 Uiso 1 1 calc R
C22 C 0.6719(2) 0.1250(2) 0.4906(2) 0.0223(5) Uani 1 1 d .
H22A H 0.7802 0.1696 0.4880 0.033 Uiso 1 1 calc R
H22B H 0.6515 0.0287 0.4944 0.033 Uiso 1 1 calc R
H22C H 0.6570 0.1787 0.5556 0.033 Uiso 1 1 calc R
I1 I 0.574301(10) 0.310854(10) 0.384926(10) 0.01197(4) Uani 1 1 d .
N1 N 0.58913(14) 0.54294(14) 0.35862(14) 0.0121(3) Uani 1 1 d .
O1 O 0.36030(13) 0.40613(13) 0.20181(13) 0.0160(3) Uani 1 1 d .
O2 O 0.34228(13) 0.59936(14) 0.33454(13) 0.0173(3) Uani 1 1 d .
O3 O 0.65919(14) 0.78339(13) 0.49008(13) 0.0172(3) Uani 1 1 d .
O4 O 0.81166(14) 0.63670(14) 0.52261(13) 0.0195(3) Uani 1 1 d .
O5 O 0.56462(15) 0.12214(13) 0.39312(14) 0.0183(3) Uani 1 1 d .
S1 S 0.43593(4) 0.54648(4) 0.27673(4) 0.01185(9) Uani 1 1 d .
S2 S 0.72439(4) 0.68514(4) 0.44653(4) 0.01218(9) Uani 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'
I I -0.4742 1.8119 '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
C2 C1 C6 122.11(15)
C2 C1 I1 118.55(11)
C6 C1 I1 119.32(14)
C1 C2 C3 118.58(15)
C2 C3 C4 121.11(19)
C3 C4 C5 118.83(16)
C3 C4 C7 120.56(19)
C5 C4 C7 120.61(15)
C6 C5 C4 121.31(15)
C5 C6 C1 118.03(18)
C13 C8 C9 121.25(13)
C13 C8 S1 118.60(12)
C9 C8 S1 120.06(13)
C10 C9 C8 118.83(17)
C9 C10 C11 120.91(16)
C12 C11 C10 118.94(14)
C12 C11 C14 119.83(18)
C10 C11 C14 121.22(17)
C13 C12 C11 120.65(17)
C8 C13 C12 119.40(15)
C16 C15 C20 120.81(14)
C16 C15 S2 119.55(14)
C20 C15 S2 119.58(11)
C15 C16 C17 118.92(17)
C18 C17 C16 121.37(15)
C17 C18 C19 118.97(14)
C17 C18 C21 121.02(17)
C19 C18 C21 120.01(19)
C20 C19 C18 120.35(18)
C19 C20 C15 119.57(15)
O5 I1 C1 91.99(6)
O5 I1 N1 175.12(6)
C1 I1 N1 83.73(5)
S2 N1 S1 121.70(8)
S2 N1 I1 118.57(7)
S1 N1 I1 117.44(7)
C22 O5 I1 113.70(12)
O2 S1 O1 117.55(8)
O2 S1 N1 113.00(9)
O1 S1 N1 104.11(8)
O2 S1 C8 107.38(8)
O1 S1 C8 108.35(9)
N1 S1 C8 105.80(7)
O4 S2 O3 118.14(10)
O4 S2 N1 105.06(8)
O3 S2 N1 111.75(8)
O4 S2 C15 107.00(7)
O3 S2 C15 107.33(7)
N1 S2 C15 106.99(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.387(3)
C1 C6 1.399(2)
C1 I1 2.0887(16)
C2 C3 1.394(2)
C3 C4 1.398(2)
C4 C5 1.399(3)
C4 C7 1.504(3)
C5 C6 1.395(3)
C8 C13 1.384(2)
C8 C9 1.392(2)
C8 S1 1.7667(14)
C9 C10 1.391(2)
C10 C11 1.399(3)
C11 C12 1.395(3)
C11 C14 1.504(2)
C12 C13 1.391(2)
C15 C16 1.389(2)
C15 C20 1.391(3)
C15 S2 1.7690(14)
C16 C17 1.396(2)
C17 C18 1.381(3)
C18 C19 1.405(3)
C18 C21 1.508(2)
C19 C20 1.390(2)
C22 O5 1.443(3)
I1 O5 1.9825(11)
I1 N1 2.4943(12)
N1 S2 1.6263(16)
N1 S1 1.6317(14)
O1 S1 1.4462(15)
O2 S1 1.4388(14)
O3 S2 1.4473(15)
O4 S2 1.4386(13)
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
C6 C1 C2 C3 -1.2(3)
I1 C1 C2 C3 177.42(13)
C1 C2 C3 C4 1.4(3)
C2 C3 C4 C5 -0.3(3)
C2 C3 C4 C7 179.29(18)
C3 C4 C5 C6 -1.1(3)
C7 C4 C5 C6 179.25(18)
C4 C5 C6 C1 1.4(3)
C2 C1 C6 C5 -0.2(3)
I1 C1 C6 C5 -178.81(12)
C13 C8 C9 C10 0.1(3)
S1 C8 C9 C10 176.61(15)
C8 C9 C10 C11 -0.1(3)
C9 C10 C11 C12 0.6(3)
C9 C10 C11 C14 -178.47(19)
C10 C11 C12 C13 -1.1(3)
C14 C11 C12 C13 178.03(19)
C9 C8 C13 C12 -0.5(3)
S1 C8 C13 C12 -177.10(14)
C11 C12 C13 C8 1.0(3)
C20 C15 C16 C17 -0.4(3)
S2 C15 C16 C17 176.78(15)
C15 C16 C17 C18 0.1(3)
C16 C17 C18 C19 0.5(3)
C16 C17 C18 C21 -178.6(2)
C17 C18 C19 C20 -0.8(3)
C21 C18 C19 C20 178.3(2)
C18 C19 C20 C15 0.5(3)
C16 C15 C20 C19 0.1(3)
S2 C15 C20 C19 -177.08(16)
C2 C1 I1 O5 110.21(13)
C6 C1 I1 O5 -71.16(14)
C2 C1 I1 N1 -67.43(13)
C6 C1 I1 N1 111.19(13)
O5 I1 N1 S2 -122.8(5)
C1 I1 N1 S2 -93.95(9)
O5 I1 N1 S1 74.1(6)
C1 I1 N1 S1 102.94(10)
C1 I1 O5 C22 99.88(13)
N1 I1 O5 C22 128.6(5)
S2 N1 S1 O2 -60.18(11)
I1 N1 S1 O2 102.37(9)
S2 N1 S1 O1 171.15(10)
I1 N1 S1 O1 -26.30(10)
S2 N1 S1 C8 57.04(13)
I1 N1 S1 C8 -140.41(9)
C13 C8 S1 O2 -171.10(14)
C9 C8 S1 O2 12.27(17)
C13 C8 S1 O1 -43.19(16)
C9 C8 S1 O1 140.18(15)
C13 C8 S1 N1 67.96(17)
C9 C8 S1 N1 -108.67(15)
S1 N1 S2 O4 163.87(10)
I1 N1 S2 O4 1.51(11)
S1 N1 S2 O3 34.59(13)
I1 N1 S2 O3 -127.77(8)
S1 N1 S2 C15 -82.62(11)
I1 N1 S2 C15 115.01(8)
C16 C15 S2 O4 -125.14(16)
C20 C15 S2 O4 52.02(19)
C16 C15 S2 O3 2.60(18)
C20 C15 S2 O3 179.76(16)
C16 C15 S2 N1 122.68(15)
C20 C15 S2 N1 -60.16(17)
