#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:32:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178786 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/40/4104088.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_4104088
loop_
_publ_author_name
'Takeo Fukuzumi'
'Jeffrey W. Bode'
_publ_section_title
;
 A Reagent for the Convenient, Solid-Phase Synthesis of N-Terminal Peptide
 Hydroxylamines for Chemoselective Ligations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3864
_journal_page_last               3865
_journal_paper_doi               10.1021/ja900601c
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H9 N O4 S'
_chemical_formula_weight         287.28
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_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
_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                   7.3767(6)
_cell_length_b                   10.9197(9)
_cell_length_c                   15.7341(14)
_cell_measurement_temperature    153(1)
_cell_volume                     1267.40(19)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      153(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5822
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8699
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0284
_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)+(0.0377P)²+0.2459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0692
_reflns_number_gt                2202
_reflns_number_total             2237
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja900601c_si_003.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4104088
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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 0.7881(2) 0.54207(16) 0.32611(10) 0.0240(4) Uani 1 1 d .
C2 C 0.7871(3) 0.57002(16) 0.24053(11) 0.0289(4) Uani 1 1 d .
H2 H 0.8794 0.5439 0.2046 0.038 Uiso 1 1 calc R
C3 C 0.6426(3) 0.63872(17) 0.21037(11) 0.0313(4) Uani 1 1 d .
H3 H 0.6371 0.6584 0.1529 0.042 Uiso 1 1 calc R
C4 C 0.5067(3) 0.67849(16) 0.26420(11) 0.0315(4) Uani 1 1 d .
H4 H 0.4109 0.7240 0.2423 0.042 Uiso 1 1 calc R
C5 C 0.5110(2) 0.65130(15) 0.35101(11) 0.0271(4) Uani 1 1 d .
H5 H 0.4198 0.6783 0.3873 0.036 Uiso 1 1 calc R
C6 C 0.6551(2) 0.58294(14) 0.38137(10) 0.0231(4) Uani 1 1 d .
C7 C 0.6946(2) 0.55400(15) 0.47243(10) 0.0234(3) Uani 1 1 d .
C8 C 0.5447(2) 0.54818(15) 0.53643(10) 0.0226(3) Uani 1 1 d .
C9 C 0.4151(2) 0.45372(16) 0.53682(10) 0.0243(4) Uani 1 1 d .
C10 C 0.2763(2) 0.45614(18) 0.59671(11) 0.0299(4) Uani 1 1 d .
H10 H 0.1907 0.3937 0.5973 0.040 Uiso 1 1 calc R
C11 C 0.2640(3) 0.55032(18) 0.65540(11) 0.0337(4) Uani 1 1 d .
H11 H 0.1716 0.5508 0.6956 0.045 Uiso 1 1 calc R
C12 C 0.3900(3) 0.64309(16) 0.65364(12) 0.0328(4) Uani 1 1 d .
H12 H 0.3816 0.7069 0.6926 0.044 Uiso 1 1 calc R
C13 C 0.5301(3) 0.64282(16) 0.59432(11) 0.0285(4) Uani 1 1 d .
H13 H 0.6140 0.7064 0.5937 0.038 Uiso 1 1 calc R
C14 C 0.4204(2) 0.35003(16) 0.47717(11) 0.0279(4) Uani 1 1 d .
H14 H 0.3247 0.2947 0.4788 0.037 Uiso 1 1 calc R
N1 N 0.8559(2) 0.47726(14) 0.48269(9) 0.0287(3) Uani 1 1 d .
O1 O 1.12491(18) 0.51806(14) 0.38018(9) 0.0430(4) Uani 1 1 d .
O2 O 0.9425(2) 0.33055(11) 0.36643(8) 0.0415(4) Uani 1 1 d .
O3 O 0.85738(18) 0.61255(12) 0.50077(7) 0.0314(3) Uani 1 1 d .
O4 O 0.53988(19) 0.33137(11) 0.42620(8) 0.0338(3) Uani 1 1 d .
S1 S 0.95285(6) 0.45865(4) 0.38235(3) 0.02939(13) 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
C2 C1 C6 122.50(16)
C2 C1 S1 127.53(14)
C6 C1 S1 109.92(12)
C1 C2 C3 117.21(17)
C4 C3 C2 121.17(16)
C3 C4 C5 121.00(17)
C6 C5 C4 118.00(16)
C5 C6 C1 120.08(15)
C5 C6 C7 126.46(15)
C1 C6 C7 113.29(15)
O3 C7 N1 62.59(10)
O3 C7 C6 111.56(13)
N1 C7 C6 112.63(14)
O3 C7 C8 115.40(13)
N1 C7 C8 120.11(13)
C6 C7 C8 120.63(15)
C13 C8 C9 119.51(15)
C13 C8 C7 117.99(15)
C9 C8 C7 122.43(14)
C10 C9 C8 119.29(16)
C10 C9 C14 117.80(16)
C8 C9 C14 122.91(15)
C11 C10 C9 120.91(17)
C12 C11 C10 119.30(17)
C11 C12 C13 120.90(17)
C8 C13 C12 120.08(17)
O4 C14 C9 124.93(16)
C7 N1 O3 57.64(10)
C7 N1 S1 107.45(10)
O3 N1 S1 106.41(10)
C7 O3 N1 59.77(10)
O2 S1 O1 119.39(9)
O2 S1 N1 104.58(8)
O1 S1 N1 109.48(8)
O2 S1 C1 112.57(9)
O1 S1 C1 111.57(8)
N1 S1 C1 96.41(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.381(2)
C1 C6 1.385(2)
C1 S1 1.7578(17)
C2 C3 1.387(3)
C3 C4 1.383(3)
C4 C5 1.398(2)
C5 C6 1.384(2)
C6 C7 1.496(2)
C7 O3 1.432(2)
C7 N1 1.464(2)
C7 C8 1.497(2)
C8 C13 1.382(2)
C8 C9 1.407(2)
C9 C10 1.391(2)
C9 C14 1.471(2)
C10 C11 1.385(3)
C11 C12 1.375(3)
C12 C13 1.393(3)
C14 O4 1.209(2)
N1 O3 1.5045(19)
N1 S1 1.7452(15)
O1 S1 1.4259(14)
O2 S1 1.4231(14)
