#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:43:41 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179761 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/57/7005768.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_7005768
loop_
_publ_author_name
'Charkoudian, Louise K.'
'Pham, David M.'
'Kwon, Ashley M.'
'Vangeloff, Abbey D.'
'Franz, Katherine J.'
_publ_section_title
;
 Modifications of boronic ester pro-chelators triggered by hydrogen
 peroxide tune reactivity to inhibit metal-promoted oxidative stress.
;
_journal_issue                   43
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5031
_journal_page_last               5042
_journal_paper_doi               10.1039/b705199a
_journal_year                    2007
_chemical_formula_moiety         'C16 H16 N2 O3'
_chemical_formula_sum            'C16 H16 N2 O3'
_chemical_formula_weight         284.31
_chemical_name_common            SBH(m-OEt)
_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                 110.1330(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5979(3)
_cell_length_b                   14.0704(3)
_cell_length_c                   9.4947(3)
_cell_measurement_reflns_used    649
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.42
_cell_measurement_theta_min      3.69
_cell_volume                     1454.74(7)
_computing_cell_refinement       SAINT
_computing_data_collection       'Apex II 2.0 Rev.2 (Bruker, 2005)'
_computing_data_reduction        'SAINT 7.12A (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL 5.1, XP (Sheldrick, 1994)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ω
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2985
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         2.37
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.9820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Sheldrick, 2004)'
_exptl_crystal_colour            'Colorless '
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needles
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0392
_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)+(0.0611P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                1954
_reflns_number_total             2985
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b705199a.txt
_cod_data_source_block           dp235
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7005768
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21916(9) 0.30620(7) 0.64770(8) 0.0519(3) Uani 1 1 d . . .
O2 O 0.10568(10) 0.63878(7) 0.43200(10) 0.0592(3) Uani 1 1 d . . .
O3 O 0.39042(12) 0.06791(9) 0.79918(10) 0.0800(4) Uani 1 1 d . . .
H3A H 0.3526 0.1093 0.7408 0.096 Uiso 0.50 1 calc PR . .
N1 N 0.27799(10) 0.14580(8) 0.53707(10) 0.0456(3) Uani 1 1 d . . .
H1A H 0.2951 0.1481 0.6326 0.055 Uiso 0.50 1 calc PR . .
N2 N 0.22350(11) 0.22164(8) 0.44772(11) 0.0473(3) Uani 1 1 d . . .
H2A H 0.2071 0.2192 0.3523 0.057 Uiso 1 1 calc R . .
C1 C 0.40545(15) -0.00855(11) 0.72077(15) 0.0548(4) Uani 1 1 d . . .
C2 C 0.46668(16) -0.08748(13) 0.79994(18) 0.0719(5) Uani 1 1 d . . .
H2B H 0.4958 -0.0869 0.9043 0.086 Uiso 1 1 calc R . .
C3 C 0.48415(16) -0.16615(13) 0.7246(2) 0.0721(5) Uani 1 1 d . . .
H3B H 0.5247 -0.2186 0.7788 0.087 Uiso 1 1 calc R . .
C4 C 0.44331(15) -0.16901(12) 0.5715(2) 0.0669(5) Uani 1 1 d . . .
H4A H 0.4553 -0.2230 0.5218 0.080 Uiso 1 1 calc R . .
C5 C 0.38403(14) -0.09067(11) 0.49171(16) 0.0565(4) Uani 1 1 d . . .
H5A H 0.3572 -0.0921 0.3875 0.068 Uiso 1 1 calc R . .
C6 C 0.36334(12) -0.00954(10) 0.56336(14) 0.0450(4) Uani 1 1 d . . .
C7 C 0.30245(13) 0.07219(10) 0.47495(13) 0.0458(4) Uani 1 1 d . . .
H7A H 0.2810 0.0705 0.3712 0.055 Uiso 1 1 calc R . .
C8 C 0.19614(12) 0.30007(9) 0.51217(12) 0.0406(3) Uani 1 1 d . . .
C9 C 0.13645(12) 0.37932(9) 0.40849(13) 0.0406(3) Uani 1 1 d . . .
C10 C 0.15266(13) 0.47023(10) 0.46947(13) 0.0446(4) Uani 1 1 d . . .
H10A H 0.2016 0.4793 0.5692 0.054 Uiso 1 1 calc R . .
C11 C 0.09627(14) 0.54728(10) 0.38253(14) 0.0466(4) Uani 1 1 d . . .
C12 C 0.02215(14) 0.53245(11) 0.23460(14) 0.0528(4) Uani 1 1 d . . .
H12A H -0.0170 0.5837 0.1757 0.063 Uiso 1 1 calc R . .
C13 C 0.00624(14) 0.44293(11) 0.17458(14) 0.0538(4) Uani 1 1 d . . .
H13A H -0.0436 0.4341 0.0752 0.065 Uiso 1 1 calc R . .
C14 C 0.06333(13) 0.36526(11) 0.25981(13) 0.0472(4) Uani 1 1 d . . .
H14A H 0.0528 0.3047 0.2181 0.057 Uiso 1 1 calc R . .
C15 C 0.17890(14) 0.65671(11) 0.58459(14) 0.0550(4) Uani 1 1 d . . .
H15A H 0.2647 0.6443 0.6004 0.066 Uiso 1 1 calc R . .
H15C H 0.1535 0.6158 0.6508 0.066 Uiso 1 1 calc R . .
C16 C 0.16123(17) 0.75878(12) 0.61637(18) 0.0678(5) Uani 1 1 d . . .
H16D H 0.2061 0.7723 0.7199 0.102 Uiso 1 1 calc R . .
H16A H 0.0755 0.7709 0.5956 0.102 Uiso 1 1 calc R . .
H16B H 0.1907 0.7986 0.5540 0.102 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 C15 117.79(11) . . ?
C1 O3 H3A 109.5 . . ?
C7 N1 N2 118.35(10) . . ?
C7 N1 H1A 120.8 . . ?
N2 N1 H1A 120.8 . . ?
C8 N2 N1 118.96(10) . . ?
C8 N2 H2A 120.5 . . ?
N1 N2 H2A 120.5 . . ?
O3 C1 C2 118.41(13) . . ?
O3 C1 C6 122.02(13) . . ?
C2 C1 C6 119.55(14) . . ?
C3 C2 C1 120.15(15) . . ?
C3 C2 H2B 119.9 . . ?
C1 C2 H2B 119.9 . . ?
C4 C3 C2 121.35(16) . . ?
C4 C3 H3B 119.3 . . ?
C2 C3 H3B 119.3 . . ?
C3 C4 C5 119.07(16) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C4 C5 C6 121.60(14) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C5 C6 C1 118.26(13) . . ?
C5 C6 C7 119.83(12) . . ?
C1 C6 C7 121.89(13) . . ?
N1 C7 C6 121.18(11) . . ?
N1 C7 H7A 119.4 . . ?
C6 C7 H7A 119.4 . . ?
O1 C8 N2 122.24(12) . . ?
O1 C8 C9 121.67(12) . . ?
N2 C8 C9 116.09(10) . . ?
C14 C9 C10 120.17(12) . . ?
C14 C9 C8 123.17(12) . . ?
C10 C9 C8 116.60(11) . . ?
C11 C10 C9 120.29(12) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
O2 C11 C10 124.74(12) . . ?
O2 C11 C12 116.08(12) . . ?
C10 C11 C12 119.16(13) . . ?
C13 C12 C11 120.52(13) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C12 C13 C14 120.93(13) . . ?
C12 C13 H13A 119.5 . . ?
C14 C13 H13A 119.5 . . ?
C13 C14 C9 118.91(13) . . ?
C13 C14 H14A 120.5 . . ?
C9 C14 H14A 120.5 . . ?
O2 C15 C16 107.42(12) . . ?
O2 C15 H15A 110.2 . . ?
C16 C15 H15A 110.2 . . ?
O2 C15 H15C 110.2 . . ?
C16 C15 H15C 110.2 . . ?
H15A C15 H15C 108.5 . . ?
C15 C16 H16D 109.5 . . ?
C15 C16 H16A 109.5 . . ?
H16D C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16D C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.2240(14) . ?
O2 C11 1.3618(16) . ?
O2 C15 1.4272(15) . ?
O3 C1 1.3532(18) . ?
O3 H3A 0.8200 . ?
N1 C7 1.2713(16) . ?
N1 N2 1.3743(14) . ?
N1 H1A 0.8600 . ?
N2 C8 1.3515(16) . ?
N2 H2A 0.8600 . ?
C1 C2 1.391(2) . ?
C1 C6 1.4035(18) . ?
C2 C3 1.371(2) . ?
C2 H2B 0.9300 . ?
C3 C4 1.365(2) . ?
C3 H3B 0.9300 . ?
C4 C5 1.380(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.3914(19) . ?
C5 H5A 0.9300 . ?
C6 C7 1.4553(18) . ?
C7 H7A 0.9300 . ?
C8 C9 1.4910(18) . ?
C9 C14 1.3882(17) . ?
C9 C10 1.3898(18) . ?
C10 C11 1.3831(18) . ?
C10 H10A 0.9300 . ?
C11 C12 1.3871(19) . ?
C12 C13 1.3686(19) . ?
C12 H12A 0.9300 . ?
C13 C14 1.3851(19) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C16 1.496(2) . ?
C15 H15A 0.9700 . ?
C15 H15C 0.9700 . ?
C16 H16D 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A N1 0.82 1.90 2.6193(13) 146.3 .
N1 H1A O3 0.86 1.95 2.6193(13) 134.1 .
N2 H2A O1 0.86 2.03 2.8586(12) 162.4 4_565
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C8 179.49(12) . . . . ?
O3 C1 C2 C3 -179.74(16) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C4 C5 C6 C7 178.87(14) . . . . ?
O3 C1 C6 C5 179.18(14) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
O3 C1 C6 C7 0.9(2) . . . . ?
C2 C1 C6 C7 -177.89(15) . . . . ?
N2 N1 C7 C6 178.19(12) . . . . ?
C5 C6 C7 N1 177.18(14) . . . . ?
C1 C6 C7 N1 -4.5(2) . . . . ?
N1 N2 C8 O1 0.6(2) . . . . ?
N1 N2 C8 C9 -179.62(11) . . . . ?
O1 C8 C9 C14 -151.79(14) . . . . ?
N2 C8 C9 C14 28.45(19) . . . . ?
O1 C8 C9 C10 25.41(19) . . . . ?
N2 C8 C9 C10 -154.36(12) . . . . ?
C14 C9 C10 C11 -0.1(2) . . . . ?
C8 C9 C10 C11 -177.38(12) . . . . ?
C15 O2 C11 C10 0.0(2) . . . . ?
C15 O2 C11 C12 178.62(13) . . . . ?
C9 C10 C11 O2 179.50(13) . . . . ?
C9 C10 C11 C12 0.9(2) . . . . ?
O2 C11 C12 C13 -179.64(13) . . . . ?
C10 C11 C12 C13 -0.9(2) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C9 0.7(2) . . . . ?
C10 C9 C14 C13 -0.7(2) . . . . ?
C8 C9 C14 C13 176.42(13) . . . . ?
C11 O2 C15 C16 -172.67(12) . . . . ?
