#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:53:30 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179027 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/25/4122549.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_4122549
loop_
_publ_author_name
'Bagchi, Vivek'
'Paraskevopoulou, Patrina'
'Das, Purak'
'Chi, Lingyu'
'Wang, Qiuwen'
'Choudhury, Amitava'
'Mathieson, Jennifer S.'
'Cronin, Leroy'
'Pardue, Daniel B.'
'Cundari, Thomas R.'
'Mitrikas, George'
'Sanakis, Yiannis'
'Stavropoulos, Pericles'
_publ_section_title
;
 A Versatile Tripodal Cu(I) Reagent for C-N Bond Construction via
 Nitrene-Transfer Chemistry: Catalytic Perspectives and Mechanistic
 Insights on C-H Aminations/Amidinations and Olefin Aziridinations.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11362
_journal_page_last               11381
_journal_paper_doi               10.1021/ja503869j
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C16 H19 N O2 S'
_chemical_formula_sum            'C16 H19 N O2 S'
_chemical_formula_weight         289.38
_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                 94.663(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.736(3)
_cell_length_b                   10.298(4)
_cell_length_c                   16.885(6)
_cell_measurement_reflns_used    1009
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.19
_cell_measurement_theta_min      2.34
_cell_volume                     1514.0(10)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2008)'
_computing_data_collection       'Bruker SMART (Bruker, 2001)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Smart-Apex CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18367
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_correction_T_min  0.9384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangularparallelopiped
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0554
_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)+(0.0789P)²+0.2443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1622
_reflns_number_gt                2315
_reflns_number_total             3750
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            Cumene_NHTs.cif
_cod_data_source_block           sad
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1514.1(9)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4122549
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
C1 C 0.7423(2) 0.7886(2) 0.64838(12) 0.0499(5) Uani 1 1 d .
C2 C 0.7808(3) 0.9154(2) 0.63355(15) 0.0664(7) Uani 1 1 d .
H2A H 0.7067 0.9711 0.6100 0.080 Uiso 1 1 calc R
C3 C 0.9274(4) 0.9613(3) 0.65302(19) 0.0876(9) Uani 1 1 d .
H3A H 0.9504 1.0476 0.6430 0.105 Uiso 1 1 calc R
C4 C 1.0385(4) 0.8818(4) 0.6866(2) 0.0925(10) Uani 1 1 d .
H4A H 1.1377 0.9127 0.6986 0.111 Uiso 1 1 calc R
C5 C 1.0028(3) 0.7557(3) 0.70263(18) 0.0825(9) Uani 1 1 d .
H5A H 1.0781 0.7007 0.7259 0.099 Uiso 1 1 calc R
C6 C 0.8562(3) 0.7097(2) 0.68451(15) 0.0629(6) Uani 1 1 d .
H6A H 0.8331 0.6242 0.6967 0.075 Uiso 1 1 calc R
C7 C 0.5798(3) 0.7357(2) 0.62845(13) 0.0551(6) Uani 1 1 d .
C8 C 0.5871(3) 0.6096(3) 0.58074(16) 0.0798(8) Uani 1 1 d .
H8A H 0.4850 0.5770 0.5683 0.120 Uiso 1 1 calc R
H8B H 0.6466 0.5464 0.6116 0.120 Uiso 1 1 calc R
H8C H 0.6343 0.6265 0.5324 0.120 Uiso 1 1 calc R
C9 C 0.4744(3) 0.8305(3) 0.58046(18) 0.0840(8) Uani 1 1 d .
H9A H 0.3749 0.7918 0.5697 0.126 Uiso 1 1 calc R
H9B H 0.5172 0.8501 0.5313 0.126 Uiso 1 1 calc R
H9C H 0.4650 0.9090 0.6103 0.126 Uiso 1 1 calc R
N1 N 0.5070(2) 0.69841(17) 0.70254(11) 0.0548(5) Uani 1 1 d .
H1A H 0.4739 0.6200 0.7049 0.066 Uiso 1 1 calc R
S1 S 0.48430(6) 0.78948(5) 0.77816(4) 0.0548(2) Uani 1 1 d .
O1 O 0.44841(19) 0.91760(15) 0.74941(11) 0.0692(5) Uani 1 1 d .
O2 O 0.37902(19) 0.72269(18) 0.82374(11) 0.0774(5) Uani 1 1 d .
C10 C 0.6596(2) 0.79831(19) 0.83768(13) 0.0484(5) Uani 1 1 d .
C11 C 0.7531(2) 0.9062(2) 0.83603(14) 0.0555(5) Uani 1 1 d .
H11A H 0.7229 0.9773 0.8045 0.067 Uiso 1 1 calc R
C12 C 0.8909(3) 0.9078(3) 0.88121(15) 0.0647(6) Uani 1 1 d .
H12A H 0.9535 0.9807 0.8799 0.078 Uiso 1 1 calc R
C13 C 0.9388(3) 0.8041(3) 0.92846(14) 0.0658(7) Uani 1 1 d .
C14 C 0.8415(3) 0.6983(3) 0.93069(15) 0.0714(7) Uani 1 1 d .
H14A H 0.8699 0.6285 0.9636 0.086 Uiso 1 1 calc R
C15 C 0.7038(3) 0.6945(2) 0.88526(15) 0.0622(6) Uani 1 1 d .
H15A H 0.6408 0.6219 0.8867 0.075 Uiso 1 1 calc R
C16 C 1.0939(4) 0.8037(4) 0.9755(2) 0.1017(11) Uani 1 1 d .
H16A H 1.1072 0.7235 1.0042 0.153 Uiso 1 1 calc R
H16B H 1.0995 0.8749 1.0123 0.153 Uiso 1 1 calc R
H16C H 1.1734 0.8124 0.9398 0.153 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
C2 C1 C6 117.3(2)
C2 C1 C7 122.2(2)
C6 C1 C7 120.4(2)
C1 C2 C3 121.2(3)
C1 C2 H2A 119.4
C3 C2 H2A 119.4
C4 C3 C2 120.7(3)
C4 C3 H3A 119.6
C2 C3 H3A 119.6
C3 C4 C5 119.2(3)
C3 C4 H4A 120.4
C5 C4 H4A 120.4
C4 C5 C6 120.4(3)
C4 C5 H5A 119.8
C6 C5 H5A 119.8
C5 C6 C1 121.1(3)
C5 C6 H6A 119.4
C1 C6 H6A 119.4
N1 C7 C9 109.16(19)
N1 C7 C8 105.10(18)
C9 C7 C8 108.1(2)
N1 C7 C1 110.85(17)
C9 C7 C1 113.4(2)
C8 C7 C1 109.85(19)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C7 N1 S1 126.95(14)
C7 N1 H1A 116.5
S1 N1 H1A 116.5
O2 S1 O1 119.69(12)
O2 S1 N1 105.92(11)
O1 S1 N1 107.80(11)
O2 S1 C10 106.61(11)
O1 S1 C10 107.56(10)
N1 S1 C10 108.94(10)
C15 C10 C11 120.0(2)
C15 C10 S1 118.87(17)
C11 C10 S1 121.16(17)
C12 C11 C10 119.5(2)
C12 C11 H11A 120.3
C10 C11 H11A 120.3
C11 C12 C13 121.6(2)
C11 C12 H12A 119.2
C13 C12 H12A 119.2
C12 C13 C14 117.9(2)
C12 C13 C16 121.5(3)
C14 C13 C16 120.6(3)
C15 C14 C13 121.3(2)
C15 C14 H14A 119.4
C13 C14 H14A 119.4
C14 C15 C10 119.7(2)
C14 C15 H15A 120.1
C10 C15 H15A 120.1
C13 C16 H16A 109.5
C13 C16 H16B 109.5
H16A C16 H16B 109.5
C13 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.376(3)
C1 C6 1.387(3)
C1 C7 1.533(3)
C2 C3 1.379(4)
C2 H2A 0.9300
C3 C4 1.358(5)
C3 H3A 0.9300
C4 C5 1.367(4)
C4 H4A 0.9300
C5 C6 1.377(4)
C5 H5A 0.9300
C6 H6A 0.9300
C7 N1 1.499(3)
C7 C9 1.528(3)
C7 C8 1.532(3)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
N1 S1 1.6096(19)
N1 H1A 0.8600
S1 O2 1.4235(18)
S1 O1 1.4318(18)
S1 C10 1.764(2)
C10 C15 1.374(3)
C10 C11 1.381(3)
C11 C12 1.372(3)
C11 H11A 0.9300
C12 C13 1.378(4)
C12 H12A 0.9300
C13 C14 1.384(4)
C13 C16 1.514(4)
C14 C15 1.373(4)
C14 H14A 0.9300
C15 H15A 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
