##############################################################################
#                                                                            #
# 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                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-2013
_journal_date_recd_electronic     2013-12-09
_journal_date_accepted     2014-01-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      2
_journal_page_first     o153
_journal_page_last     o153
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536814000257
_journal_coeditor_code     FK2077
_publ_contact_author_name     'Carsten, Strohmann'
_publ_contact_author_address
;
Fachbereich Chemie
Technische Universität Dortmund
Otto-Hahn-Strasse 6
44221 Dortmund
Germany
;
_publ_contact_author_email     'carsten.strohmann@tu-dortmund.de'
_publ_contact_author_fax     '49-231-755-3797'
_publ_contact_author_phone     '49-231-755-3825'
_publ_section_title
;
rac-2-Phenyl-1-[(2,4,6-triisopropylbenzene)sulfonyl]aziridine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Golz, Christopher' .
;
Fakultät für Chemie und Chemische Biologie
Technische Universität Dortmund
Otto-Hahn-Strasse 6
44221 Dortmund
Germany
;
    'Preut, Hans' .
;
Fakultät für Chemie und Chemische Biologie
Technische Universität Dortmund
Otto-Hahn-Strasse 6
44221 Dortmund
Germany
;
    'Strohmann, Carsten' .
;
Fakultät für Chemie und Chemische Biologie
Technische Universität Dortmund
Otto-Hahn-Strasse 6
44221 Dortmund
Germany
;
_database_code_depnum_ccdc_archive     'CCDC 979593'
_chemical_name_systematic
;
rac-2-Phenyl-1-[(2,4,6-triisopropylbenzene)sulfonyl]aziridine
;
_chemical_name_common     'N-Tris-2-phenylaziridine'
_chemical_formula_moiety     'C23 H31 N O2 S'
_chemical_formula_sum     'C23 H31 N O2 S'
_chemical_formula_iupac     'C23 H31 N O2 S'
_chemical_formula_weight     385.55
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.3037(3)
_cell_length_b     9.6995(5)
_cell_length_c     18.6675(9)
_cell_angle_alpha     75.280(4)
_cell_angle_beta     86.842(4)
_cell_angle_gamma     84.404(4)
_cell_volume     1098.11(10)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5958
_cell_measurement_theta_min     2.7080
_cell_measurement_theta_max     28.7650
_cell_measurement_temperature     173(2)
_cell_special_details     ?
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.31
_exptl_crystal_size_mid     0.05
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.166
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     416
_exptl_absorpt_coefficient_mu     0.164
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2012)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.95174
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details
;
Absorption correction: CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Agilent Xcalibur Sapphire3'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     16.0560
_diffrn_reflns_number     17550
_diffrn_reflns_av_R_equivalents     0.0445
_diffrn_reflns_theta_min     2.257
_diffrn_reflns_theta_max     25.996
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_refine_special_details     ?
_reflns_number_total     4314
_reflns_number_gt     3633
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0518
_refine_ls_R_factor_gt     0.0417
_refine_ls_wR_factor_gt     0.1007
_refine_ls_wR_factor_ref     0.1072
_refine_ls_goodness_of_fit_ref     1.058
_refine_ls_restrained_S_all     1.058
_refine_ls_number_reflns     4314
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0409P)²+0.5494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.344
_refine_diff_density_min     -0.349
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection     'CrysAlis CCD (Oxford Diffraction, 2012)'
_computing_cell_refinement     'CrysAlis CCD (Oxford Diffraction, 2012)'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2012)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL2013 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S 0.05721(6) 0.42978(4) 0.83601(2) 0.02251(13) Uani d 1 . .
    N N 0.2890(2) 0.41306(14) 0.87676(7) 0.0216(3) Uani d 1 . .
    O O1 0.01403(19) 0.28743(12) 0.83621(7) 0.0304(3) Uani d 1 . .
    O O2 -0.10310(19) 0.51063(13) 0.87007(7) 0.0319(3) Uani d 1 . .
    C C1 0.3327(3) 0.52186(18) 0.91561(10) 0.0292(4) Uani d 1 . .
    H H1A 0.2270 0.6057 0.9118 0.035 Uiso calc 1 . .
    H H1B 0.4829 0.5424 0.9172 0.035 Uiso calc 1 . .
    C C2 0.2698(3) 0.38042(18) 0.95994(9) 0.0247(4) Uani d 1 . .
    H H2 0.1206 0.3805 0.9811 0.030 Uiso calc 1 . .
    C C3 0.4221(3) 0.26355(17) 1.00030(9) 0.0228(4) Uani d 1 . .
    C C4 0.6286(3) 0.24228(19) 0.97333(10) 0.0298(4) Uani d 1 . .
    H H4 0.6741 0.3024 0.9277 0.036 Uiso calc 1 . .
    C C5 0.7692(3) 0.1342(2) 1.01235(11) 0.0349(4) Uani d 1 . .
    H H5 0.9114 0.1220 0.9939 0.042 Uiso calc 1 . .
    C C6 0.7035(3) 0.0440(2) 1.07802(11) 0.0382(5) Uani d 1 . .
    H H6 0.7998 -0.0303 1.1047 0.046 Uiso calc 1 . .
    C C7 0.4971(4) 0.0628(2) 1.10443(11) 0.0419(5) Uani d 1 . .
    H H7 0.4508 0.0002 1.1492 0.050 Uiso calc 1 . .
    C C8 0.3560(3) 0.1726(2) 1.06619(10) 0.0322(4) Uani d 1 . .
    H H8 0.2144 0.1853 1.0851 0.039 Uiso calc 1 . .
    C C9 0.1211(3) 0.52378(17) 0.74302(9) 0.0205(3) Uani d 1 . .
    C C10 0.0207(3) 0.66079(17) 0.71038(9) 0.0238(4) Uani d 1 . .
    C C11 0.0609(3) 0.71662(18) 0.63479(9) 0.0282(4) Uani d 1 . .
    H H11 -0.0067 0.8077 0.6116 0.034 Uiso calc 1 . .
    C C12 0.1947(3) 0.64572(19) 0.59189(9) 0.0286(4) Uani d 1 . .
    C C13 0.2961(3) 0.51463(18) 0.62672(9) 0.0272(4) Uani d 1 . .
    H H13 0.3914 0.4663 0.5981 0.033 Uiso calc 1 . .
    C C14 0.2649(3) 0.45043(17) 0.70157(9) 0.0222(4) Uani d 1 . .
    C C15 -0.0578(5) 0.9059(2) 0.73340(15) 0.0609(7) Uani d 1 . .
    H H15A -0.0836 0.9553 0.6815 0.091 Uiso calc 1 . .
    H H15B 0.0946 0.9011 0.7426 0.091 Uiso calc 1 . .
    H H15C -0.1392 0.9585 0.7658 0.091 Uiso calc 1 . .
    C C16 -0.1279(3) 0.75541(18) 0.74931(10) 0.0309(4) Uani d 1 . .
    H H16 -0.1170 0.7129 0.8038 0.037 Uiso calc 1 . .
    C C17 -0.3564(4) 0.7547(3) 0.73040(19) 0.0728(9) Uani d 1 . .
    H H17A -0.3732 0.7958 0.6771 0.109 Uiso calc 1 . .
    H H17B -0.4484 0.8118 0.7581 0.109 Uiso calc 1 . .
    H H17C -0.3968 0.6562 0.7436 0.109 Uiso calc 1 . .
    C C18 0.3517(5) 0.8457(3) 0.49803(14) 0.0692(8) Uani d 1 . .
    H H18A 0.2633 0.9177 0.5174 0.104 Uiso calc 1 . .
    H H18B 0.3815 0.8837 0.4450 0.104 Uiso calc 1 . .
    H H18C 0.4862 0.8219 0.5241 0.104 Uiso calc 1 . .
    C C19 0.2340(3) 0.7118(2) 0.50981(10) 0.0397(5) Uani d 1 . .
    H H19 0.3278 0.6407 0.4894 0.048 Uiso calc 1 . .
    C C20 0.0285(4) 0.7429(3) 0.46754(13) 0.0653(7) Uani d 1 . .
    H H20A -0.0443 0.6551 0.4762 0.098 Uiso calc 1 . .
    H H20B 0.0615 0.7777 0.4144 0.098 Uiso calc 1 . .
    H H20C -0.0642 0.8160 0.4847 0.098 Uiso calc 1 . .
    C C21 0.6302(3) 0.3192(2) 0.71540(13) 0.0451(5) Uani d 1 . .
    H H21A 0.6587 0.3397 0.6618 0.068 Uiso calc 1 . .
    H H21B 0.7101 0.2292 0.7397 0.068 Uiso calc 1 . .
    H H21C 0.6746 0.3971 0.7342 0.068 Uiso calc 1 . .
    C C22 0.3917(3) 0.30635(18) 0.73179(10) 0.0258(4) Uani d 1 . .
    H H22 0.3678 0.2782 0.7868 0.031 Uiso calc 1 . .
    C C23 0.3133(4) 0.1912(2) 0.69989(12) 0.0403(5) Uani d 1 . .
    H H23A 0.1611 0.1835 0.7123 0.060 Uiso calc 1 . .
    H H23B 0.3933 0.0992 0.7209 0.060 Uiso calc 1 . .
    H H23C 0.3352 0.2168 0.6459 0.060 Uiso calc 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'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
    S O1 . 1.4322(12) ?
    S O2 . 1.4382(13) ?
    S N . 1.6597(14) ?
    S C9 . 1.7880(16) ?
    N C1 . 1.478(2) ?
    N C2 . 1.504(2) ?
    C1 C2 . 1.489(2) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 C3 . 1.486(2) ?
    C2 H2 . 1.0000 ?
    C3 C4 . 1.385(2) ?
    C3 C8 . 1.389(2) ?
    C4 C5 . 1.384(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.382(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.378(3) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.390(3) ?
    C7 H7 . 0.9500 ?
    C8 H8 . 0.9500 ?
    C9 C14 . 1.415(2) ?
    C9 C10 . 1.416(2) ?
    C10 C11 . 1.396(2) ?
    C10 C16 . 1.531(2) ?
    C11 C12 . 1.385(2) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.384(2) ?
    C12 C19 . 1.520(2) ?
    C13 C14 . 1.389(2) ?
    C13 H13 . 0.9500 ?
    C14 C22 . 1.530(2) ?
    C15 C16 . 1.518(3) ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C15 H15C . 0.9800 ?
    C16 C17 . 1.503(3) ?
    C16 H16 . 1.0000 ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C18 C19 . 1.519(3) ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    C19 C20 . 1.519(3) ?
    C19 H19 . 1.0000 ?
    C20 H20A . 0.9800 ?
    C20 H20B . 0.9800 ?
    C20 H20C . 0.9800 ?
    C21 C22 . 1.528(3) ?
    C21 H21A . 0.9800 ?
    C21 H21B . 0.9800 ?
    C21 H21C . 0.9800 ?
    C22 C23 . 1.525(2) ?
    C22 H22 . 1.0000 ?
    C23 H23A . 0.9800 ?
    C23 H23B . 0.9800 ?
    C23 H23C . 0.9800 ?
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 S O2 . . 116.59(8) ?
    O1 S N . . 105.66(7) ?
    O2 S N . . 111.07(7) ?
    O1 S C9 . . 108.62(7) ?
    O2 S C9 . . 111.50(7) ?
    N S C9 . . 102.29(7) ?
    C1 N C2 . . 59.91(11) ?
    C1 N S . . 118.58(11) ?
    C2 N S . . 113.79(11) ?
    N C1 C2 . . 60.94(10) ?
    N C1 H1A . . 117.7 ?
    C2 C1 H1A . . 117.7 ?
    N C1 H1B . . 117.7 ?
    C2 C1 H1B . . 117.7 ?
    H1A C1 H1B . . 114.8 ?
    C3 C2 C1 . . 124.07(16) ?
    C3 C2 N . . 115.58(13) ?
    C1 C2 N . . 59.15(10) ?
    C3 C2 H2 . . 115.3 ?
    C1 C2 H2 . . 115.3 ?
    N C2 H2 . . 115.3 ?
    C4 C3 C8 . . 119.08(16) ?
    C4 C3 C2 . . 121.46(15) ?
    C8 C3 C2 . . 119.45(16) ?
    C5 C4 C3 . . 120.59(17) ?
    C5 C4 H4 . . 119.7 ?
    C3 C4 H4 . . 119.7 ?
    C6 C5 C4 . . 120.28(18) ?
    C6 C5 H5 . . 119.9 ?
    C4 C5 H5 . . 119.9 ?
    C7 C6 C5 . . 119.43(18) ?
    C7 C6 H6 . . 120.3 ?
    C5 C6 H6 . . 120.3 ?
    C6 C7 C8 . . 120.63(18) ?
    C6 C7 H7 . . 119.7 ?
    C8 C7 H7 . . 119.7 ?
    C3 C8 C7 . . 119.96(18) ?
    C3 C8 H8 . . 120.0 ?
    C7 C8 H8 . . 120.0 ?
    C14 C9 C10 . . 121.29(15) ?
    C14 C9 S . . 116.84(12) ?
    C10 C9 S . . 121.69(12) ?
    C11 C10 C9 . . 117.04(15) ?
    C11 C10 C16 . . 116.07(14) ?
    C9 C10 C16 . . 126.88(15) ?
    C12 C11 C10 . . 123.22(15) ?
    C12 C11 H11 . . 118.4 ?
    C10 C11 H11 . . 118.4 ?
    C13 C12 C11 . . 117.74(16) ?
    C13 C12 C19 . . 121.16(16) ?
    C11 C12 C19 . . 121.07(16) ?
    C12 C13 C14 . . 123.04(16) ?
    C12 C13 H13 . . 118.5 ?
    C14 C13 H13 . . 118.5 ?
    C13 C14 C9 . . 117.56(15) ?
    C13 C14 C22 . . 116.53(15) ?
    C9 C14 C22 . . 125.91(15) ?
    C16 C15 H15A . . 109.5 ?
    C16 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C16 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C17 C16 C15 . . 112.2(2) ?
    C17 C16 C10 . . 111.28(16) ?
    C15 C16 C10 . . 111.45(16) ?
    C17 C16 H16 . . 107.2 ?
    C15 C16 H16 . . 107.2 ?
    C10 C16 H16 . . 107.2 ?
    C16 C17 H17A . . 109.5 ?
    C16 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C16 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C19 C18 H18A . . 109.5 ?
    C19 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C19 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    C20 C19 C18 . . 111.1(2) ?
    C20 C19 C12 . . 111.87(18) ?
    C18 C19 C12 . . 110.91(17) ?
    C20 C19 H19 . . 107.6 ?
    C18 C19 H19 . . 107.6 ?
    C12 C19 H19 . . 107.6 ?
    C19 C20 H20A . . 109.5 ?
    C19 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    C19 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    C22 C21 H21A . . 109.5 ?
    C22 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C22 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    C23 C22 C21 . . 111.22(16) ?
    C23 C22 C14 . . 110.57(14) ?
    C21 C22 C14 . . 110.51(15) ?
    C23 C22 H22 . . 108.1 ?
    C21 C22 H22 . . 108.1 ?
    C14 C22 H22 . . 108.1 ?
    C22 C23 H23A . . 109.5 ?
    C22 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C22 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
_shelxl_version_number        2.013
