##############################################################################
# #
# This CIF contains the data in a paper accepted for publication in #
# Acta Crystallographica Section E. It conforms to the requirements of #
# Notes for Authors for Acta Crystallographica Section E, and has been #
# peer reviewed under the auspices of the IUCr Commission on Journals. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary is obtainable from #
# ftp://ftp.iucr.org/pub/cif_core.dic. #
# #
# Software is freely available for graphical display of the structure(s) #
# in this CIF. For information consult the CIF software page #
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data_global
_audit_creation_method SHELXL-97
_journal_date_recd_electronic 2012-03-12
_journal_date_accepted 2012-03-16
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2012
_journal_volume 68
_journal_issue 4
_journal_page_first o1138
_journal_page_last o1139
_journal_paper_category QO
_journal_paper_doi 10.1107/S1600536812011440
_journal_coeditor_code HB6679
_publ_contact_author_name ' Edward RT Tiekink '
_publ_contact_author_address
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email
;
edward.tiekink@gmail.com
;
_publ_contact_author_fax ' +60 3 7967 4193 '
_publ_contact_author_phone ' +60 3 7967 6775 '
_publ_section_title
;\
(2S,3R)-tert-Butyl
N-[4-(N-benzyl-4-fluorobenzenesulfonamido)-3-hydroxy-1-\
phenylbutan-2-yl]carbamate
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Marcele Moreth' .
;
Instituto de Tecnologia em F\'armacos--Farmanguinhos,
FioCruz--Funda\,c\~ao Oswaldo Cruz, R. Sizenando Nabuco, 100, Manguinhos,
21041-250 Rio de Janeiro,
RJ, Brazil
;
'Marcus V.N. de Souza' .
;
Instituto de Tecnologia em F\'armacos--Farmanguinhos,
FioCruz--Funda\,c\~ao Oswaldo Cruz, R. Sizenando Nabuco, 100, Manguinhos,
21041-250 Rio de Janeiro,
RJ, Brazil
;
'Wardell, James L.'
;
Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.
;
;
Centro de Desenvolvimento Tecnol\'ogico em Sa\'ude (CDTS),
Funda\,c\~ao Oswaldo Cruz (FIOCRUZ), Casa Amarela,
Campus de Manguinhos, Av. Brasil 4365,
21040-900 Rio de Janeiro, RJ, Brazil
;
'Solange M. S. V. Wardell' .
;
CHEMSOL, 1 Harcourt Road, Aberdeen, AB15 5NY, Scotland
;
'Tiekink, Edward R. T.' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
data_I
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(2S,3R)-tert-Butyl
N-[4-(N-benzyl-4-fluorobenzenesulfonamido)-3-hydroxy-1-
phenylbutan-2-yl]carbamate
;
_chemical_name_common ?
_chemical_formula_moiety 'C28 H33 F N2 O5 S'
_chemical_formula_sum 'C28 H33 F N2 O5 S'
_chemical_formula_iupac 'C28 H33 F N2 O5 S'
_chemical_formula_weight 528.62
_chemical_melting_point ?
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21'
_symmetry_space_group_name_Hall 'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 5.41160(10)
_cell_length_b 25.5513(8)
_cell_length_c 9.8615(3)
_cell_angle_alpha 90.00
_cell_angle_beta 101.641(2)
_cell_angle_gamma 90.00
_cell_volume 1335.54(6)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 11534
_cell_measurement_theta_min 2.91
_cell_measurement_theta_max 27.48
_cell_measurement_temperature 120(2)
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.50
_exptl_crystal_size_mid 0.24
_exptl_crystal_size_min 0.18
_exptl_crystal_density_diffrn 1.315
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 560
_exptl_absorpt_coefficient_mu 0.169
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2007)'
_exptl_absorpt_correction_T_min 0.6535
_exptl_absorpt_correction_T_max 0.7456
_diffrn_ambient_temperature 120(2)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'Bruker--Nonius FR591 rotating anode'
_diffrn_radiation_monochromator 'graphite'
_diffrn_measurement_device_type
;
Bruker--Nonius Roper CCD camera on a \k-goniostat
;
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_reflns_number 12832
_diffrn_reflns_av_R_equivalents 0.0401
_diffrn_reflns_av_sigmaI/netI 0.0619
_diffrn_reflns_theta_min 3.19
_diffrn_reflns_theta_max 27.50
_diffrn_reflns_theta_full 27.50
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_k_min -32
_diffrn_reflns_limit_k_max 33
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
2\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total 5956
_reflns_number_gt 5075
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0547
_refine_ls_R_factor_gt 0.0424
_refine_ls_wR_factor_gt 0.0956
_refine_ls_wR_factor_ref 0.1027
_refine_ls_goodness_of_fit_ref 1.013
_refine_ls_restrained_S_all 1.012
_refine_ls_number_reflns 5956
_refine_ls_number_parameters 343
_refine_ls_number_restraints 3
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0535P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.206
_refine_diff_density_min -0.334
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack (1983), 2848 Friedel pairs'
_refine_ls_abs_structure_Flack 0.06(6)
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'
'F' 'F' 0.0171 0.0103
'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'
_computing_data_collection 'COLLECT (Hooft, 1998)'
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material 'publCIF (Westrip, 2010)'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.52180(9) 0.91034(2) 0.52242(6) 0.02540(14) Uani d . 1 1 . .
F F1 1.2856(3) 0.99049(6) 0.98111(16) 0.0480(4) Uani d . 1 1 . .
O O1 0.4439(3) 0.95265(6) 0.42835(19) 0.0382(4) Uani d . 1 1 . .
O O2 0.3377(3) 0.88381(6) 0.58349(18) 0.0320(4) Uani d . 1 1 . .
O O3 0.9825(3) 0.81562(6) 0.68221(15) 0.0258(3) Uani d D 1 1 . .
H H3O 1.088(4) 0.8377(8) 0.667(3) 0.039 Uiso d D 1 1 . .
O O4 0.4133(2) 0.69554(6) 0.41684(14) 0.0213(3) Uani d . 1 1 . .
O O5 0.6340(3) 0.65982(6) 0.26540(15) 0.0221(3) Uani d . 1 1 . .
N N1 0.6512(3) 0.86650(7) 0.44103(19) 0.0247(4) Uani d . 1 1 . .
N N2 0.8407(3) 0.70276(7) 0.44759(18) 0.0196(4) Uani d D 1 1 . .
H H2N 0.976(3) 0.6946(9) 0.415(2) 0.024 Uiso d D 1 1 . .
C C1 0.7491(4) 0.93595(8) 0.6604(2) 0.0227(5) Uani d . 1 1 . .
C C2 0.7357(4) 0.92322(9) 0.7956(3) 0.0305(5) Uani d . 1 1 . .
H H2 0.6034 0.9015 0.8134 0.037 Uiso calc R 1 1 . .
C C3 0.9165(5) 0.94237(10) 0.9048(3) 0.0369(6) Uani d . 1 1 . .
H H3 0.9092 0.9344 0.9980 0.044 Uiso calc R 1 1 . .
C C4 1.1047(5) 0.97287(9) 0.8743(3) 0.0335(6) Uani d . 1 1 . .
C C5 1.1211(4) 0.98673(10) 0.7422(3) 0.0333(6) Uani d . 1 1 . .
H H5 1.2540 1.0086 0.7260 0.040 Uiso calc R 1 1 . .
C C6 0.9407(4) 0.96826(9) 0.6328(3) 0.0274(5) Uani d . 1 1 . .
H H6 0.9473 0.9775 0.5402 0.033 Uiso calc R 1 1 . .
C C7 0.7982(5) 0.88253(9) 0.3363(2) 0.0286(5) Uani d . 1 1 . .
H H7A 0.9790 0.8747 0.3714 0.034 Uiso calc R 1 1 . .
H H7B 0.7809 0.9208 0.3209 0.034 Uiso calc R 1 1 . .
C C8 0.7080(4) 0.85424(8) 0.2005(2) 0.0237(5) Uani d . 1 1 . .
C C9 0.4706(4) 0.86529(9) 0.1202(2) 0.0286(5) Uani d . 1 1 . .
H H9 0.3643 0.8901 0.1520 0.034 Uiso calc R 1 1 . .
C C10 0.3890(4) 0.84028(10) -0.0058(2) 0.0294(5) Uani d . 1 1 . .
H H10 0.2262 0.8477 -0.0593 0.035 Uiso calc R 1 1 . .
C C11 0.5432(4) 0.80475(9) -0.0538(2) 0.0299(5) Uani d . 1 1 . .
H H11 0.4876 0.7881 -0.1407 0.036 Uiso calc R 1 1 . .
C C12 0.7775(5) 0.79355(10) 0.0244(3) 0.0353(6) Uani d . 1 1 . .
H H12 0.8841 0.7690 -0.0081 0.042 Uiso calc R 1 1 . .
C C13 0.8579(4) 0.81823(10) 0.1514(2) 0.0311(5) Uani d . 1 1 . .
H H13 1.0195 0.8101 0.2053 0.037 Uiso calc R 1 1 . .
C C14 0.6509(4) 0.81084(8) 0.4777(2) 0.0227(5) Uani d . 1 1 . .
H H14A 0.5950 0.7903 0.3919 0.027 Uiso calc R 1 1 . .
H H14B 0.5254 0.8054 0.5368 0.027 Uiso calc R 1 1 . .
C C15 0.9042(4) 0.78940(8) 0.5533(2) 0.0188(4) Uani d . 1 1 . .
H H15 1.0331 0.7949 0.4949 0.023 Uiso calc R 1 1 . .
C C16 0.8788(4) 0.73051(8) 0.5795(2) 0.0185(4) Uani d . 1 1 . .
H H16 0.7262 0.7251 0.6205 0.022 Uiso calc R 1 1 . .
C C17 0.6120(4) 0.68657(8) 0.3804(2) 0.0184(4) Uani d . 1 1 . .
C C18 0.4078(4) 0.64183(8) 0.1668(2) 0.0216(5) Uani d . 1 1 . .
C C19 0.2370(4) 0.68815(9) 0.1142(2) 0.0282(5) Uani d . 1 1 . .
H H19A 0.3397 0.7173 0.0918 0.042 Uiso calc R 1 1 . .
H H19B 0.1466 0.6992 0.1860 0.042 Uiso calc R 1 1 . .
H H19C 0.1152 0.6778 0.0309 0.042 Uiso calc R 1 1 . .
C C20 0.5227(4) 0.61986(10) 0.0506(2) 0.0308(5) Uani d . 1 1 . .
H H20A 0.6410 0.5918 0.0868 0.046 Uiso calc R 1 1 . .
H H20B 0.6125 0.6477 0.0123 0.046 Uiso calc R 1 1 . .
H H20C 0.3886 0.6059 -0.0223 0.046 Uiso calc R 1 1 . .
C C21 0.2728(4) 0.59978(9) 0.2324(3) 0.0297(5) Uani d . 1 1 . .
H H21A 0.1835 0.6159 0.2989 0.045 Uiso calc R 1 1 . .
H H21B 0.3963 0.5745 0.2804 0.045 Uiso calc R 1 1 . .
H H21C 0.1514 0.5818 0.1603 0.045 Uiso calc R 1 1 . .
C C22 1.1081(4) 0.70785(8) 0.6797(2) 0.0207(4) Uani d . 1 1 . .
H H22A 1.2620 0.7146 0.6427 0.025 Uiso calc R 1 1 . .
H H22B 1.1273 0.7259 0.7700 0.025 Uiso calc R 1 1 . .
C C23 1.0838(4) 0.64964(8) 0.7015(2) 0.0198(4) Uani d . 1 1 . .
C C24 1.2408(4) 0.61396(9) 0.6537(2) 0.0240(5) Uani d . 1 1 . .
H H24 1.3646 0.6263 0.6055 0.029 Uiso calc R 1 1 . .
C C25 1.2194(4) 0.56056(10) 0.6754(3) 0.0312(5) Uani d . 1 1 . .
H H25 1.3294 0.5366 0.6435 0.037 Uiso calc R 1 1 . .
C C26 1.0372(5) 0.54250(9) 0.7437(3) 0.0320(6) Uani d . 1 1 . .
H H26 1.0212 0.5060 0.7582 0.038 Uiso calc R 1 1 . .
C C27 0.8783(4) 0.57718(9) 0.7909(3) 0.0287(5) Uani d . 1 1 . .
H H27 0.7521 0.5645 0.8370 0.034 Uiso calc R 1 1 . .
C C28 0.9026(4) 0.63017(9) 0.7710(2) 0.0236(5) Uani d . 1 1 . .
H H28 0.7944 0.6538 0.8052 0.028 Uiso calc R 1 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0209(3) 0.0212(3) 0.0315(3) -0.0010(2) -0.0008(2) 0.0019(2)
F1 0.0509(9) 0.0460(9) 0.0388(9) -0.0038(8) -0.0106(7) -0.0181(7)
O1 0.0352(10) 0.0244(9) 0.0473(11) 0.0013(7) -0.0099(8) 0.0079(8)
O2 0.0186(8) 0.0303(9) 0.0468(11) -0.0037(6) 0.0056(7) -0.0027(8)
O3 0.0302(8) 0.0282(9) 0.0167(8) -0.0058(7) -0.0009(6) -0.0049(7)
O4 0.0173(7) 0.0293(8) 0.0178(8) -0.0033(6) 0.0050(6) -0.0059(6)
O5 0.0160(7) 0.0316(8) 0.0176(8) -0.0012(6) 0.0012(6) -0.0076(6)
N1 0.0297(10) 0.0237(10) 0.0206(10) -0.0041(8) 0.0050(8) 0.0039(8)
N2 0.0165(9) 0.0280(10) 0.0140(9) -0.0019(7) 0.0025(7) -0.0040(7)
C1 0.0194(10) 0.0211(11) 0.0269(13) 0.0018(9) 0.0028(9) -0.0028(9)
C2 0.0316(12) 0.0276(13) 0.0335(14) -0.0022(10) 0.0091(10) 0.0039(10)
C3 0.0454(15) 0.0358(14) 0.0272(14) 0.0024(12) 0.0016(11) -0.0034(11)
C4 0.0383(14) 0.0243(12) 0.0329(14) 0.0041(10) -0.0044(11) -0.0102(10)
C5 0.0262(12) 0.0296(13) 0.0436(16) -0.0063(10) 0.0059(11) -0.0124(11)
C6 0.0282(12) 0.0237(11) 0.0309(13) -0.0039(9) 0.0073(10) -0.0052(10)
C7 0.0288(12) 0.0325(13) 0.0235(12) -0.0097(10) 0.0028(10) 0.0057(10)
C8 0.0231(11) 0.0250(11) 0.0221(12) -0.0057(9) 0.0027(9) 0.0073(9)
C9 0.0288(12) 0.0340(13) 0.0222(12) 0.0030(10) 0.0034(9) 0.0024(10)
C10 0.0241(11) 0.0432(14) 0.0192(12) -0.0031(10) -0.0001(9) 0.0014(10)
C11 0.0362(13) 0.0315(13) 0.0223(12) -0.0071(10) 0.0064(10) 0.0000(10)
C12 0.0348(13) 0.0356(14) 0.0365(15) 0.0038(11) 0.0094(11) -0.0026(11)
C13 0.0225(11) 0.0396(14) 0.0300(14) 0.0011(11) 0.0024(9) 0.0064(11)
C14 0.0224(10) 0.0229(11) 0.0217(11) -0.0047(9) 0.0018(8) 0.0005(9)
C15 0.0187(10) 0.0230(11) 0.0146(10) -0.0048(8) 0.0028(8) -0.0019(8)
C16 0.0185(10) 0.0244(10) 0.0126(10) -0.0033(8) 0.0031(8) -0.0034(8)
C17 0.0213(10) 0.0187(10) 0.0150(10) -0.0010(8) 0.0033(8) 0.0003(8)
C18 0.0178(10) 0.0270(11) 0.0179(11) -0.0037(9) -0.0015(8) -0.0059(9)
C19 0.0291(12) 0.0306(13) 0.0228(12) 0.0025(10) 0.0004(9) 0.0007(10)
C20 0.0281(12) 0.0425(14) 0.0212(12) -0.0018(11) 0.0035(9) -0.0140(11)
C21 0.0283(12) 0.0263(12) 0.0344(14) -0.0023(10) 0.0063(10) -0.0048(10)
C22 0.0188(10) 0.0265(11) 0.0164(11) -0.0017(9) 0.0024(8) -0.0024(9)
C23 0.0179(10) 0.0273(12) 0.0121(10) 0.0003(9) -0.0015(8) -0.0015(8)
C24 0.0221(10) 0.0316(12) 0.0183(11) -0.0004(9) 0.0044(9) -0.0028(9)
C25 0.0314(13) 0.0309(13) 0.0311(14) 0.0052(10) 0.0058(11) -0.0085(10)
C26 0.0330(13) 0.0256(12) 0.0349(15) -0.0027(10) 0.0007(11) -0.0016(10)
C27 0.0248(12) 0.0338(13) 0.0275(13) -0.0020(10) 0.0051(10) 0.0028(10)
C28 0.0210(11) 0.0292(12) 0.0202(12) 0.0016(9) 0.0030(8) 0.0002(9)
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.4313(17) ?
S1 O2 . 1.4341(17) ?
S1 N1 . 1.618(2) ?
S1 C1 . 1.765(2) ?
F1 C4 . 1.362(3) ?
O3 C15 . 1.424(2) ?
O3 H3O . 0.840(10) ?
O4 C17 . 1.222(2) ?
O5 C17 . 1.350(2) ?
O5 C18 . 1.475(2) ?
N1 C14 . 1.468(3) ?
N1 C7 . 1.483(3) ?
N2 C17 . 1.346(3) ?
N2 C16 . 1.459(3) ?
N2 H2N . 0.877(10) ?
C1 C2 . 1.389(3) ?
C1 C6 . 1.394(3) ?
C2 C3 . 1.390(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.363(4) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.371(4) ?
C5 C6 . 1.383(3) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.514(3) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C13 . 1.377(3) ?
C8 C9 . 1.395(3) ?
C9 C10 . 1.388(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.380(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.375(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.391(3) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 C15 . 1.524(3) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.537(3) ?
C15 H15 . 1.0000 ?
C16 C22 . 1.535(3) ?
C16 H16 . 1.0000 ?
C18 C20 . 1.517(3) ?
C18 C21 . 1.516(3) ?
C18 C19 . 1.527(3) ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
C22 C23 . 1.512(3) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 C24 . 1.392(3) ?
C23 C28 . 1.397(3) ?
C24 C25 . 1.390(3) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.380(4) ?
C25 H25 . 0.9500 ?
C26 C27 . 1.380(3) ?
C26 H26 . 0.9500 ?
C27 C28 . 1.378(3) ?
C27 H27 . 0.9500 ?
C28 H28 . 0.9500 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . 119.38(10) ?
O1 S1 N1 . . 107.57(11) ?
O2 S1 N1 . . 106.73(10) ?
O1 S1 C1 . . 106.72(10) ?
O2 S1 C1 . . 106.66(10) ?
N1 S1 C1 . . 109.56(10) ?
C15 O3 H3O . . 104.1(18) ?
C17 O5 C18 . . 120.63(16) ?
C14 N1 C7 . . 117.84(19) ?
C14 N1 S1 . . 121.78(15) ?
C7 N1 S1 . . 120.07(16) ?
C17 N2 C16 . . 122.62(17) ?
C17 N2 H2N . . 119.9(15) ?
C16 N2 H2N . . 117.3(15) ?
C2 C1 C6 . . 120.7(2) ?
C2 C1 S1 . . 119.32(17) ?
C6 C1 S1 . . 119.95(18) ?
C3 C2 C1 . . 119.8(2) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C4 C3 C2 . . 118.1(2) ?
C4 C3 H3 . . 121.0 ?
C2 C3 H3 . . 121.0 ?
F1 C4 C3 . . 118.1(2) ?
F1 C4 C5 . . 118.4(2) ?
C3 C4 C5 . . 123.5(2) ?
C4 C5 C6 . . 118.8(2) ?
C4 C5 H5 . . 120.6 ?
C6 C5 H5 . . 120.6 ?
C5 C6 C1 . . 119.0(2) ?
C5 C6 H6 . . 120.5 ?
C1 C6 H6 . . 120.5 ?
N1 C7 C8 . . 111.22(18) ?
N1 C7 H7A . . 109.4 ?
C8 C7 H7A . . 109.4 ?
N1 C7 H7B . . 109.4 ?
C8 C7 H7B . . 109.4 ?
H7A C7 H7B . . 108.0 ?
C13 C8 C9 . . 118.4(2) ?
C13 C8 C7 . . 121.49(19) ?
C9 C8 C7 . . 120.1(2) ?
C10 C9 C8 . . 120.3(2) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C11 C10 C9 . . 120.3(2) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
C12 C11 C10 . . 119.8(2) ?
C12 C11 H11 . . 120.1 ?
C10 C11 H11 . . 120.1 ?
C11 C12 C13 . . 119.8(2) ?
C11 C12 H12 . . 120.1 ?
C13 C12 H12 . . 120.1 ?
C8 C13 C12 . . 121.3(2) ?
C8 C13 H13 . . 119.3 ?
C12 C13 H13 . . 119.3 ?
N1 C14 C15 . . 115.05(17) ?
N1 C14 H14A . . 108.5 ?
C15 C14 H14A . . 108.5 ?
N1 C14 H14B . . 108.5 ?
C15 C14 H14B . . 108.5 ?
H14A C14 H14B . . 107.5 ?
O3 C15 C14 . . 110.10(17) ?
O3 C15 C16 . . 109.35(16) ?
C14 C15 C16 . . 109.39(16) ?
O3 C15 H15 . . 109.3 ?
C14 C15 H15 . . 109.3 ?
C16 C15 H15 . . 109.3 ?
N2 C16 C22 . . 109.95(16) ?
N2 C16 C15 . . 109.11(16) ?
C22 C16 C15 . . 112.91(16) ?
N2 C16 H16 . . 108.3 ?
C22 C16 H16 . . 108.3 ?
C15 C16 H16 . . 108.3 ?
O4 C17 N2 . . 125.01(19) ?
O4 C17 O5 . . 125.03(18) ?
N2 C17 O5 . . 109.95(17) ?
O5 C18 C20 . . 101.61(16) ?
O5 C18 C21 . . 110.29(17) ?
C20 C18 C21 . . 111.49(18) ?
O5 C18 C19 . . 110.33(17) ?
C20 C18 C19 . . 110.02(19) ?
C21 C18 C19 . . 112.58(18) ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C18 C20 H20A . . 109.5 ?
C18 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C18 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C18 C21 H21A . . 109.5 ?
C18 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C18 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C23 C22 C16 . . 112.36(17) ?
C23 C22 H22A . . 109.1 ?
C16 C22 H22A . . 109.1 ?
C23 C22 H22B . . 109.1 ?
C16 C22 H22B . . 109.1 ?
H22A C22 H22B . . 107.9 ?
C24 C23 C28 . . 118.0(2) ?
C24 C23 C22 . . 121.33(19) ?
C28 C23 C22 . . 120.64(19) ?
C25 C24 C23 . . 121.0(2) ?
C25 C24 H24 . . 119.5 ?
C23 C24 H24 . . 119.5 ?
C26 C25 C24 . . 119.6(2) ?
C26 C25 H25 . . 120.2 ?
C24 C25 H25 . . 120.2 ?
C25 C26 C27 . . 120.3(2) ?
C25 C26 H26 . . 119.8 ?
C27 C26 H26 . . 119.8 ?
C28 C27 C26 . . 119.9(2) ?
C28 C27 H27 . . 120.0 ?
C26 C27 H27 . . 120.0 ?
C27 C28 C23 . . 121.1(2) ?
C27 C28 H28 . . 119.4 ?
C23 C28 H28 . . 119.4 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 N1 C14 . . . . -152.35(16) ?
O2 S1 N1 C14 . . . . -23.12(19) ?
C1 S1 N1 C14 . . . . 92.00(18) ?
O1 S1 N1 C7 . . . . 34.24(19) ?
O2 S1 N1 C7 . . . . 163.48(15) ?
C1 S1 N1 C7 . . . . -81.40(18) ?
O1 S1 C1 C2 . . . . 135.22(18) ?
O2 S1 C1 C2 . . . . 6.6(2) ?
N1 S1 C1 C2 . . . . -108.60(19) ?
O1 S1 C1 C6 . . . . -45.3(2) ?
O2 S1 C1 C6 . . . . -173.95(17) ?
N1 S1 C1 C6 . . . . 70.89(19) ?
C6 C1 C2 C3 . . . . -0.7(3) ?
S1 C1 C2 C3 . . . . 178.78(18) ?
C1 C2 C3 C4 . . . . -0.8(4) ?
C2 C3 C4 F1 . . . . -178.3(2) ?
C2 C3 C4 C5 . . . . 1.8(4) ?
F1 C4 C5 C6 . . . . 178.8(2) ?
C3 C4 C5 C6 . . . . -1.2(4) ?
C4 C5 C6 C1 . . . . -0.3(3) ?
C2 C1 C6 C5 . . . . 1.3(3) ?
S1 C1 C6 C5 . . . . -178.21(18) ?
C14 N1 C7 C8 . . . . 58.6(3) ?
S1 N1 C7 C8 . . . . -127.76(17) ?
N1 C7 C8 C13 . . . . -112.8(2) ?
N1 C7 C8 C9 . . . . 68.8(3) ?
C13 C8 C9 C10 . . . . 0.1(3) ?
C7 C8 C9 C10 . . . . 178.6(2) ?
C8 C9 C10 C11 . . . . -0.9(4) ?
C9 C10 C11 C12 . . . . 0.9(4) ?
C10 C11 C12 C13 . . . . -0.2(4) ?
C9 C8 C13 C12 . . . . 0.6(3) ?
C7 C8 C13 C12 . . . . -177.9(2) ?
C11 C12 C13 C8 . . . . -0.5(4) ?
C7 N1 C14 C15 . . . . 66.9(2) ?
S1 N1 C14 C15 . . . . -106.61(19) ?
N1 C14 C15 O3 . . . . 62.2(2) ?
N1 C14 C15 C16 . . . . -177.57(18) ?
C17 N2 C16 C22 . . . . 135.09(19) ?
C17 N2 C16 C15 . . . . -100.6(2) ?
O3 C15 C16 N2 . . . . -170.49(15) ?
C14 C15 C16 N2 . . . . 68.9(2) ?
O3 C15 C16 C22 . . . . -47.9(2) ?
C14 C15 C16 C22 . . . . -168.55(17) ?
C16 N2 C17 O4 . . . . 4.3(3) ?
C16 N2 C17 O5 . . . . -176.89(17) ?
C18 O5 C17 O4 . . . . 4.3(3) ?
C18 O5 C17 N2 . . . . -174.58(17) ?
C17 O5 C18 C20 . . . . 174.12(18) ?
C17 O5 C18 C21 . . . . -67.5(2) ?
C17 O5 C18 C19 . . . . 57.5(2) ?
N2 C16 C22 C23 . . . . -56.3(2) ?
C15 C16 C22 C23 . . . . -178.44(17) ?
C16 C22 C23 C24 . . . . 112.4(2) ?
C16 C22 C23 C28 . . . . -67.9(2) ?
C28 C23 C24 C25 . . . . -0.5(3) ?
C22 C23 C24 C25 . . . . 179.28(19) ?
C23 C24 C25 C26 . . . . 0.9(3) ?
C24 C25 C26 C27 . . . . -0.4(3) ?
C25 C26 C27 C28 . . . . -0.6(4) ?
C26 C27 C28 C23 . . . . 1.1(3) ?
C24 C23 C28 C27 . . . . -0.5(3) ?
C22 C23 C28 C27 . . . . 179.71(19) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2n O4 1_655 0.882(17) 2.363(17) 3.179(2) 154.0(17)
O3 H3o O2 1_655 0.84(2) 2.08(2) 2.904(2) 166(3)
C7 H7A O2 1_655 0.99 2.56 3.405(3) 143
C22 H22A O4 1_655 0.99 2.57 3.358(2) 137
C20 H20C Cg1 1_454 0.98 2.78 3.719(2) 160