#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/58/4025836.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_4025836
loop_
_publ_author_name
'Nohemy A. Sorto'
'Marilyn M. Olmstead'
'Jared T. Shaw'
_publ_section_title
;
 Practical Synthesis of PC190723, an Inhibitor of the Bacterial Cell
 Division Protein FtsZ
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7946
_journal_page_last               7949
_journal_paper_doi               10.1021/jo101720y
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C14 H7 Cl2 F N2 O3'
_chemical_formula_sum            'C14 H7 Cl2 F N2 O3'
_chemical_formula_weight         341.12
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                63.0260(10)
_cell_angle_beta                 77.877(2)
_cell_angle_gamma                71.216(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4638(11)
_cell_length_b                   9.5592(13)
_cell_length_c                   10.0336(14)
_cell_measurement_reflns_used    9224
_cell_measurement_temperature    87(2)
_cell_measurement_theta_max      30.6
_cell_measurement_theta_min      2.45
_cell_volume                     682.97(16)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'Apex2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      87(2)
_diffrn_detector_area_resol_mean 0.833
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART Apex DUO'
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9949
_diffrn_reflns_theta_full        29.13
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.501
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3652
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0421P)²+0.3458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0871
_reflns_number_gt                3535
_reflns_number_total             3652
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo101720y_si_001.cif
_cod_data_source_block           mn2021
_cod_database_code               4025836
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 Cl 0.21717(4) 0.69730(3) 0.19671(3) 0.02287(9) Uani 1 1 d . . .
Cl2 Cl 0.30797(5) 0.14657(4) 0.00476(3) 0.02636(9) Uani 1 1 d . . .
F1 F -0.16658(9) 0.07318(10) 0.61432(9) 0.02334(17) Uani 1 1 d . . .
O1 O -0.05768(11) 0.48475(11) 0.33627(10) 0.02262(19) Uani 1 1 d . . .
O2 O 0.44801(11) 0.10239(10) 0.66990(10) 0.01799(17) Uani 1 1 d . . .
O3 O 0.52186(11) 0.42977(11) 0.36034(10) 0.02010(18) Uani 1 1 d . . .
N1 N 0.29133(12) 0.33181(12) 0.41566(10) 0.01373(18) Uani 1 1 d . . .
N2 N 0.24471(16) 0.57524(13) 0.00675(12) 0.0231(2) Uani 1 1 d . . .
C1 C -0.07629(15) 0.34918(16) 0.41294(14) 0.0202(2) Uani 1 1 d . . .
H1 H -0.1762 0.3288 0.4058 0.024 Uiso 1 1 calc R . .
C2 C 0.04516(14) 0.21320(14) 0.51672(12) 0.0153(2) Uani 1 1 d . . .
C3 C -0.00997(14) 0.07789(15) 0.62342(14) 0.0176(2) Uani 1 1 d . . .
C4 C 0.08059(16) -0.04841(15) 0.73885(14) 0.0202(2) Uani 1 1 d . . .
H4 H 0.0388 -0.1395 0.8058 0.024 Uiso 1 1 calc R . .
C5 C 0.23533(16) -0.03788(14) 0.75399(13) 0.0197(2) Uani 1 1 d . . .
H5 H 0.2995 -0.1206 0.8346 0.024 Uiso 1 1 calc R . .
C6 C 0.29598(14) 0.09380(14) 0.65094(12) 0.0155(2) Uani 1 1 d . . .
C7 C 0.20775(14) 0.21545(13) 0.52777(12) 0.0133(2) Uani 1 1 d . . .
C8 C 0.44904(15) 0.26933(14) 0.61997(13) 0.0168(2) Uani 1 1 d . . .
H8A H 0.5561 0.2746 0.6402 0.020 Uiso 1 1 calc R . .
H8B H 0.3564 0.3226 0.6738 0.020 Uiso 1 1 calc R . .
C9 C 0.42784(14) 0.35408(13) 0.45352(13) 0.0151(2) Uani 1 1 d . . .
C10 C 0.27977(14) 0.37504(13) 0.26072(12) 0.0139(2) Uani 1 1 d . . .
C11 C 0.25116(15) 0.53548(14) 0.15064(13) 0.0170(2) Uani 1 1 d . . .
C12 C 0.26261(18) 0.45685(16) -0.03626(14) 0.0232(3) Uani 1 1 d . . .
H12 H 0.2578 0.4844 -0.1392 0.028 Uiso 1 1 calc R . .
C13 C 0.28799(15) 0.29492(14) 0.06561(13) 0.0180(2) Uani 1 1 d . . .
C14 C 0.29926(14) 0.25243(14) 0.21594(12) 0.0152(2) Uani 1 1 d . . .
H14 H 0.3199 0.1419 0.2865 0.018 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
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
C6 O2 C8 110.48(8) . . ?
C9 N1 C7 118.70(9) . . ?
C9 N1 C10 117.86(9) . . ?
C7 N1 C10 119.10(9) . . ?
C11 N2 C12 118.58(10) . . ?
O1 C1 C2 124.86(11) . . ?
O1 C1 H1 117.6 . . ?
C2 C1 H1 117.6 . . ?
C3 C2 C7 116.57(10) . . ?
C3 C2 C1 117.93(10) . . ?
C7 C2 C1 125.15(10) . . ?
F1 C3 C4 117.74(10) . . ?
F1 C3 C2 117.46(10) . . ?
C4 C3 C2 124.78(11) . . ?
C3 C4 C5 117.62(11) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C6 C5 C4 119.86(11) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
O2 C6 C5 118.63(10) . . ?
O2 C6 C7 119.54(10) . . ?
C5 C6 C7 121.82(11) . . ?
C6 C7 C2 118.97(10) . . ?
C6 C7 N1 117.66(10) . . ?
C2 C7 N1 123.30(10) . . ?
O2 C8 C9 107.65(9) . . ?
O2 C8 H8A 110.2 . . ?
C9 C8 H8A 110.2 . . ?
O2 C8 H8B 110.2 . . ?
C9 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
O3 C9 N1 122.66(10) . . ?
O3 C9 C8 124.33(10) . . ?
N1 C9 C8 112.97(10) . . ?
C14 C10 C11 117.85(10) . . ?
C14 C10 N1 118.70(10) . . ?
C11 C10 N1 123.44(10) . . ?
N2 C11 C10 123.51(11) . . ?
N2 C11 Cl1 115.24(9) . . ?
C10 C11 Cl1 121.23(9) . . ?
N2 C12 C13 121.80(11) . . ?
N2 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 119.72(11) . . ?
C14 C13 Cl2 120.22(9) . . ?
C12 C13 Cl2 120.05(9) . . ?
C10 C14 C13 118.50(10) . . ?
C10 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
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
Cl1 C11 1.7307(12) . ?
Cl2 C13 1.7321(12) . ?
F1 C3 1.3640(13) . ?
O1 C1 1.2133(16) . ?
O2 C6 1.3724(14) . ?
O2 C8 1.4421(14) . ?
O3 C9 1.2146(14) . ?
N1 C9 1.3931(14) . ?
N1 C7 1.4284(14) . ?
N1 C10 1.4326(14) . ?
N2 C11 1.3243(15) . ?
N2 C12 1.3399(17) . ?
C1 C2 1.4805(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.3999(16) . ?
C2 C7 1.4113(15) . ?
C3 C4 1.3765(17) . ?
C4 C5 1.3895(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3891(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.4007(15) . ?
C8 C9 1.5109(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C14 1.3874(16) . ?
C10 C11 1.4025(15) . ?
C12 C13 1.3891(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3888(16) . ?
C14 H14 0.9500 . ?
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
O1 C1 C2 C3 164.66(13) . . . . ?
O1 C1 C2 C7 -8.3(2) . . . . ?
C7 C2 C3 F1 -179.78(10) . . . . ?
C1 C2 C3 F1 6.70(16) . . . . ?
C7 C2 C3 C4 1.97(18) . . . . ?
C1 C2 C3 C4 -171.56(12) . . . . ?
F1 C3 C4 C5 -175.68(11) . . . . ?
C2 C3 C4 C5 2.57(19) . . . . ?
C3 C4 C5 C6 -2.50(19) . . . . ?
C8 O2 C6 C5 -146.43(11) . . . . ?
C8 O2 C6 C7 34.68(14) . . . . ?
C4 C5 C6 O2 179.01(11) . . . . ?
C4 C5 C6 C7 -2.12(19) . . . . ?
O2 C6 C7 C2 -174.38(10) . . . . ?
C5 C6 C7 C2 6.76(17) . . . . ?
O2 C6 C7 N1 8.45(16) . . . . ?
C5 C6 C7 N1 -170.41(11) . . . . ?
C3 C2 C7 C6 -6.47(16) . . . . ?
C1 C2 C7 C6 166.53(11) . . . . ?
C3 C2 C7 N1 170.53(10) . . . . ?
C1 C2 C7 N1 -16.47(18) . . . . ?
C9 N1 C7 C6 -20.85(15) . . . . ?
C10 N1 C7 C6 135.28(11) . . . . ?
C9 N1 C7 C2 162.12(11) . . . . ?
C10 N1 C7 C2 -41.76(15) . . . . ?
C6 O2 C8 C9 -63.64(12) . . . . ?
C7 N1 C9 O3 167.68(11) . . . . ?
C10 N1 C9 O3 11.26(16) . . . . ?
C7 N1 C9 C8 -10.09(14) . . . . ?
C10 N1 C9 C8 -166.51(9) . . . . ?
O2 C8 C9 O3 -126.23(12) . . . . ?
O2 C8 C9 N1 51.49(12) . . . . ?
C9 N1 C10 C14 112.01(12) . . . . ?
C7 N1 C10 C14 -44.32(14) . . . . ?
C9 N1 C10 C11 -67.37(15) . . . . ?
C7 N1 C10 C11 136.30(12) . . . . ?
C12 N2 C11 C10 1.6(2) . . . . ?
C12 N2 C11 Cl1 -177.15(10) . . . . ?
C14 C10 C11 N2 -1.18(18) . . . . ?
N1 C10 C11 N2 178.20(11) . . . . ?
C14 C10 C11 Cl1 177.45(9) . . . . ?
N1 C10 C11 Cl1 -3.16(16) . . . . ?
C11 N2 C12 C13 -0.2(2) . . . . ?
N2 C12 C13 C14 -1.5(2) . . . . ?
N2 C12 C13 Cl2 179.24(11) . . . . ?
C11 C10 C14 C13 -0.57(16) . . . . ?
N1 C10 C14 C13 -179.98(10) . . . . ?
C12 C13 C14 C10 1.85(18) . . . . ?
Cl2 C13 C14 C10 -178.92(9) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659309
