#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:36:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178474 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/95/4029595.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_4029595
loop_
_publ_author_name
'Dev, Dharm'
'Palakurthy, Nani Babu'
'Thalluri, Kishore'
'Chandra, Jyoti'
'Mandal, Bhubaneswar'
_publ_section_title
;
 Ethyl 2-Cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate (o-NosylOXY): A
 Recyclable Coupling Reagent for Racemization-Free Synthesis of Peptide,
 Amide, Hydroxamate, and Ester.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5420
_journal_page_last               5431
_journal_paper_doi               10.1021/jo500292m
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C16 H13 N2 O4'
_chemical_formula_weight         297.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9579(4)
_cell_length_b                   8.2268(7)
_cell_length_c                   29.991(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1469.99(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.873
_diffrn_measured_fraction_theta_max 0.873
_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  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0884
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            4355
_diffrn_reflns_theta_full        28.82
_diffrn_reflns_theta_max         28.82
_diffrn_reflns_theta_min         3.21
_exptl_absorpt_coefficient_mu    0.098
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             620
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0612
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1567
_refine_ls_wR_factor_ref         0.1986
_reflns_number_gt                1834
_reflns_number_total             3019
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500292m_si_002.cif
_cod_data_source_block           exp_783
_cod_depositor_comments          'Adding full bibliography for 4029595.cif.'
_cod_original_cell_volume        1470.0(2)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               4029595
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
C5 C 0.4066(5) 0.5224(4) 0.51061(11) 0.0362(8) Uani 1 1 d .
C7 C 0.6622(6) 0.5309(4) 0.44708(11) 0.0384(8) Uani 1 1 d .
H7 H 0.7955 0.4993 0.4335 0.046 Uiso 1 1 calc R
C8 C 0.5149(5) 0.6290(4) 0.42452(11) 0.0363(7) Uani 1 1 d .
C6 C 0.6143(5) 0.4776(4) 0.49057(11) 0.0337(7) Uani 1 1 d .
C1 C 0.7662(6) 0.3822(4) 0.51564(12) 0.0408(8) Uani 1 1 d .
H1 H 0.9015 0.3505 0.5029 0.049 Uiso 1 1 calc R
C3 C 0.5154(6) 0.3815(5) 0.57774(14) 0.0564(11) Uani 1 1 d .
H3 H 0.4852 0.3507 0.6070 0.068 Uiso 1 1 calc R
C12 C 1.0249(6) 0.6670(5) 0.31271(13) 0.0487(9) Uani 1 1 d .
C11 C 0.5636(6) 0.7000(5) 0.38076(13) 0.0456(9) Uani 1 1 d .
C10 C 0.2546(5) 0.6183(4) 0.48565(13) 0.0408(8) Uani 1 1 d .
H10 H 0.1166 0.6454 0.4981 0.049 Uiso 1 1 calc R
C9 C 0.3047(6) 0.6718(4) 0.44407(12) 0.0433(9) Uani 1 1 d .
H9 H 0.2030 0.7359 0.4284 0.052 Uiso 1 1 calc R
C4 C 0.3605(7) 0.4709(5) 0.55472(13) 0.0486(9) Uani 1 1 d .
H4 H 0.2246 0.4979 0.5680 0.058 Uiso 1 1 calc R
C2 C 0.7180(7) 0.3359(5) 0.55806(13) 0.0529(10) Uani 1 1 d .
H2 H 0.8204 0.2736 0.5740 0.063 Uiso 1 1 calc R
C14 C 1.1381(8) 0.7517(6) 0.27401(14) 0.0606(11) Uani 1 1 d .
O1 O 0.4512(5) 0.7960(4) 0.36057(10) 0.0618(8) Uani 1 1 d .
O2 O 0.7697(4) 0.6449(3) 0.36480(8) 0.0507(7) Uani 1 1 d .
O4 O 1.3148(5) 0.6691(4) 0.26230(10) 0.0636(8) Uani 1 1 d .
O3 O 1.0691(7) 0.8714(5) 0.25750(12) 0.1027(15) Uani 1 1 d .
N1 N 0.8454(6) 0.7311(4) 0.32720(11) 0.0558(9) Uani 1 1 d .
C15 C 1.4473(9) 0.7290(7) 0.22421(16) 0.0818(16) Uani 1 1 d .
H15A H 1.4337 0.8463 0.2224 0.098 Uiso 1 1 calc R
H15B H 1.6043 0.7029 0.2288 0.098 Uiso 1 1 calc R
C16 C 1.3741(14) 0.6592(9) 0.1839(2) 0.147(4) Uani 1 1 d .
H16A H 1.3646 0.5434 0.1873 0.221 Uiso 1 1 calc R
H16B H 1.4787 0.6850 0.1606 0.221 Uiso 1 1 calc R
H16C H 1.2289 0.7017 0.1764 0.221 Uiso 1 1 calc R
C13 C 1.1250(7) 0.5243(5) 0.33199(13) 0.0502(9) Uani 1 1 d .
N2 N 1.2004(7) 0.4126(5) 0.34841(13) 0.0729(12) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C10 C5 C4 122.5(3)
C10 C5 C6 118.5(3)
C4 C5 C6 119.0(3)
C8 C7 C6 120.8(3)
C7 C8 C9 120.3(3)
C7 C8 C11 123.3(3)
C9 C8 C11 116.3(3)
C7 C6 C1 122.4(3)
C7 C6 C5 119.2(3)
C1 C6 C5 118.4(3)
C2 C1 C6 121.2(3)
C4 C3 C2 121.0(4)
N1 C12 C13 123.4(3)
N1 C12 C14 116.6(3)
C13 C12 C14 120.0(3)
O1 C11 O2 122.2(3)
O1 C11 C8 127.1(4)
O2 C11 C8 110.6(3)
C9 C10 C5 121.8(3)
C10 C9 C8 119.4(3)
C3 C4 C5 120.1(3)
C1 C2 C3 120.2(4)
O3 C14 O4 127.3(4)
O3 C14 C12 123.6(4)
O4 C14 C12 109.1(4)
C11 O2 N1 113.2(3)
C14 O4 C15 117.9(4)
C12 N1 O2 109.6(3)
C16 C15 O4 111.3(5)
N2 C13 C12 177.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C5 C10 1.416(5)
C5 C4 1.416(5)
C5 C6 1.424(4)
C7 C8 1.371(4)
C7 C6 1.405(4)
C8 C9 1.427(5)
C8 C11 1.465(5)
C6 C1 1.415(4)
C1 C2 1.359(5)
C3 C4 1.367(5)
C3 C2 1.395(5)
C12 N1 1.269(5)
C12 C13 1.439(6)
C12 C14 1.512(5)
C11 O1 1.199(4)
C11 O2 1.394(4)
C10 C9 1.356(5)
C14 O3 1.176(5)
C14 O4 1.301(5)
O2 N1 1.407(4)
O4 C15 1.473(5)
C15 C16 1.407(8)
C13 N2 1.135(5)
