#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:37:58 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178908 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/37/4113726.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_4113726
loop_
_publ_author_name
'Ajay Mandal'
'Donald Hilvert'
_publ_section_title
;
 Charge Optimization Increases the Potency and Selectivity of a Chorismate
 Mutase Inhibitor
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5598
_journal_page_last               5599
_journal_paper_doi               10.1021/ja029447t
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C9 H10 N2 O4'
_chemical_formula_weight         210.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 119.69(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.707(7)
_cell_length_b                   7.050(4)
_cell_length_c                   13.174(7)
_cell_measurement_reflns_used    16
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.1
_cell_measurement_theta_min      7.9
_cell_volume                     1912.8(18)
_computing_cell_refinement       CAD4
_computing_data_collection       CAD4
_computing_data_reduction        MolEN
_computing_molecular_graphics    'Ortep, Platon'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.657
_diffrn_measured_fraction_theta_max 0.658
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       ο/2π
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0114
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            1877
_diffrn_reflns_theta_full        24.96
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  10000s
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.117
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          .35
_exptl_crystal_size_mid          .35
_exptl_crystal_size_min          .1
_refine_diff_density_max         2.468
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   6.823
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      6.462
_refine_ls_R_factor_all          0.2672
_refine_ls_R_factor_gt           0.2676
_refine_ls_shift/su_max          0.246
_refine_ls_shift/su_mean         0.053
_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          0.6371
_refine_ls_wR_factor_ref         0.6819
_reflns_number_gt                1107
_reflns_number_total             1721
_reflns_threshold_expression     >3sigma(I)
_cod_data_source_file            ja029447tsi20021126_094215.cif
_cod_data_source_block           h031001
_cod_original_cell_volume        1912.8(16)
_cod_original_sg_symbol_H-M      'C 1 c 1'
_cod_database_code               4113726
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.2909(5) 0.1517(18) 0.1396(10) 0.068(4) Uani 1 1 d .
C2 C 0.3826(7) 0.274(2) 0.3696(12) 0.050(4) Uani 1 1 d .
O3 O 0.3308(6) 0.6484(14) 0.2371(17) 0.103(6) Uani 1 1 d .
C4 C 0.3072(6) 0.3125(18) 0.3005(16) 0.049(4) Uani 1 1 d .
H4A H 0.2836 0.2115 0.3132 0.059 Uiso 1 1 calc R
H4B H 0.2968 0.4322 0.3237 0.059 Uiso 1 1 calc R
C5 C 0.3957(9) 0.082(2) 0.323(2) 0.122(11) Uani 1 1 d .
H5A H 0.4418 0.0706 0.3504 0.146 Uiso 1 1 calc R
H5B H 0.3830 -0.0234 0.3546 0.146 Uiso 1 1 calc R
O6 O 0.4697(7) 0.222(2) 0.5624(11) 0.100(6) Uani 1 1 d .
C7 C 0.3860(14) 0.535(4) 0.2401(18) 0.124(12) Uani 1 1 d .
H7 H 0.4144 0.5966 0.2158 0.149 Uiso 1 1 calc R
C8 C 0.3158(9) 0.482(3) 0.1454(18) 0.077(5) Uani 1 1 d .
H8 H 0.3000 0.5105 0.0628 0.092 Uiso 1 1 calc R
C9 C 0.3578(9) 0.073(2) 0.1891(16) 0.068(5) Uani 1 1 d .
H9 H 0.3540 -0.0603 0.1663 0.082 Uiso 1 1 calc R
N10 N 0.4135(12) 0.221(3) 0.4950(16) 0.119(9) Uani 1 1 d .
C11 C 0.2921(9) 0.3181(18) 0.1792(14) 0.074(6) Uani 1 1 d .
C12 C 0.4132(9) 0.467(3) 0.3551(13) 0.081(7) Uani 1 1 d .
H12A H 0.4082 0.5640 0.4023 0.097 Uiso 1 1 calc R
H12B H 0.4593 0.4480 0.3858 0.097 Uiso 1 1 calc R
C13 C 0.3898(8) 0.184(3) 0.1245(17) 0.082(7) Uani 1 1 d .
N14 N 0.4261(14) 0.231(2) 0.0996(18) 0.112(8) Uani 1 1 d .
O15 O 0.3729(10) 0.227(3) 0.5359(15) 0.151(9) 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
C11 O1 C9 110.9(13)
N10 C2 C5 97.7(17)
N10 C2 C4 118.6(15)
C5 C2 C4 108.0(11)
N10 C2 C12 110.0(13)
C5 C2 C12 119.8(17)
C4 C2 C12 103.6(13)
C7 O3 C8 59.8(10)
C11 C4 C2 103.2(12)
C9 C5 C2 111.5(13)
C12 C7 O3 97.8(16)
C12 C7 C8 121.5(15)
O3 C7 C8 62.5(16)
C11 C8 C7 111.7(16)
C11 C8 O3 109.3(16)
C7 C8 O3 57.7(14)
O1 C9 C5 112.2(14)
O1 C9 C13 105.7(14)
C5 C9 C13 115.6(15)
O6 N10 O15 118.4(19)
O6 N10 C2 125.9(18)
O15 N10 C2 113(2)
O1 C11 C8 122.7(19)
O1 C11 C4 111.6(12)
C8 C11 C4 115.9(13)
C7 C12 C2 115.2(12)
N14 C13 C9 161(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C11 1.278(19)
O1 C9 1.49(2)
C2 N10 1.49(2)
C2 C5 1.57(2)
C2 C4 1.577(19)
C2 C12 1.60(2)
O3 C7 1.52(3)
O3 C8 1.59(2)
C4 C11 1.46(2)
C5 C9 1.54(3)
O6 N10 1.18(2)
C7 C12 1.40(3)
C7 C8 1.55(3)
C8 C11 1.45(2)
C9 C13 1.60(3)
N10 O15 1.32(3)
C13 N14 1.11(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
N10 C2 C4 C11 -168.1(15)
C5 C2 C4 C11 -58.4(18)
C12 C2 C4 C11 69.6(13)
N10 C2 C5 C9 169.1(17)
C4 C2 C5 C9 46(2)
C12 C2 C5 C9 -72.5(19)
C8 O3 C7 C12 -121.5(15)
C12 C7 C8 C11 -18(3)
O3 C7 C8 C11 -100(2)
C12 C7 C8 O3 82(2)
C7 O3 C8 C11 104.0(17)
C11 O1 C9 C5 52.7(18)
C11 O1 C9 C13 -74.0(17)
C2 C5 C9 O1 -40(2)
C2 C5 C9 C13 81(2)
C5 C2 N10 O6 79(3)
C4 C2 N10 O6 -165(2)
C12 C2 N10 O6 -46(3)
C5 C2 N10 O15 -120(2)
C4 C2 N10 O15 -5(3)
C12 C2 N10 O15 114(2)
C9 O1 C11 C8 71(2)
C9 O1 C11 C4 -73.2(18)
C7 C8 C11 O1 -101(2)
O3 C8 C11 O1 -162.8(14)
C7 C8 C11 C4 42(2)
O3 C8 C11 C4 -20(2)
C2 C4 C11 O1 76.1(16)
C2 C4 C11 C8 -70.9(19)
O3 C7 C12 C2 87.3(19)
C8 C7 C12 C2 25(3)
N10 C2 C12 C7 -178(2)
C5 C2 C12 C7 70(3)
C4 C2 C12 C7 -50(2)
O1 C9 C13 N14 178(5)
C5 C9 C13 N14 54(6)
