#------------------------------------------------------------------------------
#$Date: 2017-03-04 15:58:23 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193508 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/54/4125451.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_4125451
loop_
_publ_author_name
'Maestre, Lourdes'
'Dorel, Ruth'
'Pablo, Óscar'
'Escofet, Imma'
'Sameera, W. M. C.'
'Álvarez, Eleuterio'
'Maseras, Feliu'
'Díaz-Requejo, M Mar'
'Echavarren, Antonio M.'
'Pérez, Pedro J'
_publ_section_title
;
 Functional-Group-Tolerant, Silver-Catalyzed N-N Bond Formation by Nitrene
 Transfer to Amines.
;
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2216
_journal_page_last               2223
_journal_paper_doi               10.1021/jacs.6b08219
_journal_volume                  139
_journal_year                    2017
_chemical_formula_sum            'C16 H24 N2 O3 S'
_chemical_formula_weight         324.43
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 91.8438(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3182(13)
_cell_length_b                   7.3622(7)
_cell_length_c                   15.3001(13)
_cell_measurement_temperature    100(2)
_cell_volume                     1612.0(3)
_computing_cell_refinement
'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_reduction
'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 200
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.795
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.795
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            79700
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.795
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         62.577
_diffrn_reflns_theta_min         2.664
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_current           24
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       Unknown
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         20935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0531P)²+0.0776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.1040
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17307
_reflns_number_total             20935
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b08219_si_006.cif
_cod_data_source_block           OS475
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4125450--4125451.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4125451
_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.
;
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.958
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
C1 C 0.27985(2) 0.27973(4) 0.08427(2) 0.01216(4) Uani 1 1 d
C2 C 0.24889(2) 0.30264(4) -0.01104(2) 0.01431(4) Uani 1 1 d
C3 C 0.40206(2) 0.28894(5) -0.05695(2) 0.01408(4) Uani 1 1 d
C4 C 0.43984(2) 0.26229(4) 0.03541(2) 0.01197(4) Uani 1 1 d
C5 C 0.41128(2) 0.29801(4) 0.19273(2) 0.01245(4) Uani 1 1 d
C6 C 0.50894(2) 0.36211(5) 0.21046(2) 0.01391(4) Uani 1 1 d
C7 C 0.58421(2) 0.25836(5) 0.22823(2) 0.01616(5) Uani 1 1 d
C8 C 0.67928(3) 0.34458(8) 0.23945(3) 0.02254(7) Uani 1 1 d
C9 C 0.58346(4) 0.05511(7) 0.23746(4) 0.02636(8) Uani 1 1 d
C10 C 0.22198(2) 0.73029(4) 0.06957(2) 0.01246(4) Uani 1 1 d
C11 C 0.22940(2) 0.81969(5) -0.01035(2) 0.01528(4) Uani 1 1 d
C12 C 0.15007(3) 0.84486(5) -0.06382(2) 0.01638(5) Uani 1 1 d
C13 C 0.06235(2) 0.78171(5) -0.03940(2) 0.01531(4) Uani 1 1 d
C14 C 0.05614(2) 0.69481(5) 0.04148(2) 0.01574(4) Uani 1 1 d
C15 C 0.13516(2) 0.66902(4) 0.09587(2) 0.01396(4) Uani 1 1 d
C16 C -0.02249(3) 0.80823(6) -0.09896(3) 0.02153(6) Uani 1 1 d
H6 H 0.5175(6) 0.4911(14) 0.2054(6) 0.025(2) Uiso 1 1 d
H11 H 0.2831(6) 0.1522(12) 0.0984(6) 0.0183(18) Uiso 1 1 d
H12 H 0.2398(6) 0.3432(12) 0.1232(6) 0.0202(18) Uiso 1 1 d
H21 H 0.2433(6) 0.4263(12) -0.0253(5) 0.0180(17) Uiso 1 1 d
H22 H 0.1908(6) 0.2373(12) -0.0206(6) 0.0186(17) Uiso 1 1 d
H31 H 0.3990(6) 0.4167(12) -0.0695(5) 0.0162(16) Uiso 1 1 d
H32 H 0.4437(6) 0.2214(12) -0.0957(6) 0.0195(18) Uiso 1 1 d
H41 H 0.5008(7) 0.3176(12) 0.0416(6) 0.022(2) Uiso 1 1 d
H42 H 0.4406(6) 0.1426(13) 0.0485(6) 0.022(2) Uiso 1 1 d
H51 H 0.4082(6) 0.1701(11) 0.1931(6) 0.0169(17) Uiso 1 1 d
H52 H 0.3691(6) 0.3513(12) 0.2315(6) 0.0198(18) Uiso 1 1 d
H81 H 0.6754(7) 0.4730(14) 0.2346(6) 0.029(2) Uiso 1 1 d
H82 H 0.7217(7) 0.2982(14) 0.1977(7) 0.031(2) Uiso 1 1 d
H83 H 0.7062(7) 0.3178(13) 0.2944(7) 0.031(2) Uiso 1 1 d
H91 H 0.6285(7) 0.0044(16) 0.2006(7) 0.039(3) Uiso 1 1 d
H92 H 0.5236(7) 0.0054(17) 0.2290(7) 0.042(3) Uiso 1 1 d
H93 H 0.6050(7) 0.0227(15) 0.2967(7) 0.039(3) Uiso 1 1 d
H161 H -0.0672(9) 0.7048(17) -0.0904(9) 0.055(4) Uiso 1 1 d
H162 H -0.0027(11) 0.823(2) -0.1572(11) 0.073(5) Uiso 1 1 d
H163 H -0.0597(8) 0.9049(16) -0.0809(7) 0.043(3) Uiso 1 1 d
H11A H 0.2907(6) 0.8610(12) -0.0284(6) 0.0212(19) Uiso 1 1 d
H12A H 0.1554(7) 0.9099(13) -0.1173(6) 0.027(2) Uiso 1 1 d
H14A H -0.0009(6) 0.6475(12) 0.0604(6) 0.0210(19) Uiso 1 1 d
H15A H 0.1299(6) 0.6095(12) 0.1518(6) 0.0209(19) Uiso 1 1 d
N1 N 0.38928(2) 0.54800(3) 0.08397(2) 0.01168(3) Uani 1 1 d
N2 N 0.37758(2) 0.35369(3) 0.10049(2) 0.01009(3) Uani 1 1 d
O1 O 0.29420(2) 0.62944(4) 0.21850(2) 0.01697(4) Uani 1 1 d
O2 O 0.37737(2) 0.85847(3) 0.13056(2) 0.01840(4) Uani 1 1 d
O3 O 0.31074(2) 0.21254(4) -0.06778(2) 0.01508(4) Uani 1 1 d
S1 S 0.32566(2) 0.68910(2) 0.13413(2) 0.01192(2) 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'
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
N2 C1 C2 110.90(2)
O3 C2 C1 111.43(3)
O3 C3 C4 110.89(3)
C3 C4 N2 110.89(3)
C6 C5 N2 110.38(2)
C7 C6 C5 126.77(3)
C6 C7 C9 125.29(3)
C6 C7 C8 120.01(4)
C9 C7 C8 114.70(4)
C15 C10 C11 119.95(3)
C15 C10 S1 121.30(2)
C11 C10 S1 118.70(2)
C12 C11 C10 119.64(3)
C11 C12 C13 121.40(3)
C14 C13 C12 118.08(3)
C14 C13 C16 121.41(3)
C12 C13 C16 120.50(3)
C15 C14 C13 121.10(3)
C10 C15 C14 119.82(3)
N2 N1 S1 118.909(19)
N1 N2 C1 115.69(2)
N1 N2 C4 104.34(2)
C1 N2 C4 107.02(2)
N1 N2 C5 112.72(2)
C1 N2 C5 108.46(2)
C4 N2 C5 108.17(2)
C2 O3 C3 109.32(2)
O1 S1 O2 117.859(19)
O1 S1 N1 115.472(16)
O2 S1 N1 103.973(17)
O1 S1 C10 105.546(17)
O2 S1 C10 104.457(17)
N1 S1 C10 108.817(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.5145(4)
C1 C2 1.5199(5)
C2 O3 1.4239(4)
C3 O3 1.4281(4)
C3 C4 1.5097(5)
C4 N2 1.5153(4)
C5 C6 1.4923(5)
C5 N2 1.5326(4)
C6 C7 1.3416(5)
C7 C9 1.5031(6)
C7 C8 1.5068(6)
C10 C15 1.3939(4)
C10 C11 1.3957(5)
C10 S1 1.7825(3)
C11 C12 1.3907(5)
C12 C13 1.4012(5)
C13 C14 1.3985(5)
C13 C16 1.5076(6)
C14 C15 1.3957(5)
N1 N2 1.4632(4)
N1 S1 1.5947(3)
O1 S1 1.4491(3)
O2 S1 1.4521(3)
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
N2 C1 C2 O3 58.65(3)
O3 C3 C4 N2 -60.35(3)
N2 C5 C6 C7 -118.43(3)
C5 C6 C7 C9 -2.77(6)
C5 C6 C7 C8 176.43(3)
C15 C10 C11 C12 -0.87(5)
S1 C10 C11 C12 176.68(3)
C10 C11 C12 C13 -0.22(6)
C11 C12 C13 C14 1.13(6)
C11 C12 C13 C16 -179.16(4)
C12 C13 C14 C15 -0.98(5)
C16 C13 C14 C15 179.31(4)
C11 C10 C15 C14 1.01(5)
S1 C10 C15 C14 -176.47(3)
C13 C14 C15 C10 -0.08(5)
S1 N1 N2 C1 56.49(3)
S1 N1 N2 C4 173.76(2)
S1 N1 N2 C5 -69.12(3)
C2 C1 N2 N1 61.84(3)
C2 C1 N2 C4 -53.93(3)
C2 C1 N2 C5 -170.41(2)
C3 C4 N2 N1 -68.10(3)
C3 C4 N2 C1 55.00(3)
C3 C4 N2 C5 171.67(2)
C6 C5 N2 N1 -52.70(3)
C6 C5 N2 C1 177.88(2)
C6 C5 N2 C4 62.13(3)
C1 C2 O3 C3 -60.98(3)
C4 C3 O3 C2 61.78(4)
N2 N1 S1 O1 27.85(3)
N2 N1 S1 O2 158.54(2)
N2 N1 S1 C10 -90.57(2)
C15 C10 S1 O1 -13.56(3)
C11 C10 S1 O1 168.93(3)
C15 C10 S1 O2 -138.49(3)
C11 C10 S1 O2 43.99(3)
C15 C10 S1 N1 110.94(3)
C11 C10 S1 N1 -66.57(3)
