#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/56/7005666.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_7005666
loop_
_publ_author_name
'Bernhardt, Paul V.'
'Chin, Piao'
'Sharpe, Philip C.'
'Richardson, Des R.'
_publ_section_title
;
 Hydrazone chelators for the treatment of iron overload disorders: iron
 coordination chemistry and biological activity.
;
_journal_issue                   30
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3232
_journal_page_last               3244
_journal_paper_doi               10.1039/b704102k
_journal_year                    2007
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C13 H11 Br1 N3 O, Cl O4, 2(H2 O))'
_chemical_formula_sum            'C13 H15 Br Cl N3 O7'
_chemical_formula_weight         440.64
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2007-03-16T15:16:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90.079(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.839(5)
_cell_length_b                   16.527(5)
_cell_length_c                   15.507(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.234
_cell_measurement_theta_min      10.135
_cell_measurement_wavelength     0.71073
_cell_volume                     1752.7(15)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_orient_matrix_type
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      0.108239
_diffrn_orient_matrix_UB_12      -0.017424
_diffrn_orient_matrix_UB_13      0.039227
_diffrn_orient_matrix_UB_21      -0.00943
_diffrn_orient_matrix_UB_22      -0.056252
_diffrn_orient_matrix_UB_23      -0.023385
_diffrn_orient_matrix_UB_31      0.097873
_diffrn_orient_matrix_UB_32      0.013887
_diffrn_orient_matrix_UB_33      -0.045533
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3356
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.8
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        -3
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.538
_exptl_absorpt_correction_T_max  0.8843
_exptl_absorpt_correction_T_min  0.7669
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was 5
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.67
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.08
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0574P)²+1.2660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1
_refine_ls_wR_factor_ref         0.1157
_reflns_number_gt                1991
_reflns_number_total             3082
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b704102k.txt
_cod_data_source_block           2049ac43
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7005666
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
C1 C -0.6626(7) 0.0635(3) 1.1506(3) 0.0770(14) Uani 1 1 d . . .
H1 H -0.6498 0.0075 1.15 0.092 Uiso 1 1 calc R . .
C2 C -0.8230(7) 0.0987(4) 1.1878(3) 0.0864(17) Uani 1 1 d . . .
H2 H -0.9201 0.0668 1.2124 0.104 Uiso 1 1 calc R . .
C3 C -0.8387(7) 0.1804(4) 1.1885(3) 0.0794(15) Uani 1 1 d . . .
H3 H -0.9467 0.205 1.2138 0.095 Uiso 1 1 calc R . .
C4 C -0.6957(6) 0.2265(3) 1.1520(3) 0.0628(12) Uani 1 1 d . . .
H4 H -0.7061 0.2826 1.1529 0.075 Uiso 1 1 calc R . .
C5 C -0.5367(6) 0.1908(2) 1.1140(2) 0.0488(10) Uani 1 1 d . . .
C6 C -0.3807(6) 0.2371(3) 1.0737(2) 0.0507(10) Uani 1 1 d . . .
H6 H -0.3841 0.2933 1.0725 0.061 Uiso 1 1 calc R . .
C7 C 0.0522(6) 0.1986(2) 0.9650(2) 0.0486(9) Uani 1 1 d . . .
C8 C 0.2168(5) 0.2449(2) 0.9250(2) 0.0475(9) Uani 1 1 d . . .
C9 C 0.3567(6) 0.2003(2) 0.8807(2) 0.0496(10) Uani 1 1 d . . .
H9 H 0.3415 0.1447 0.8741 0.06 Uiso 1 1 calc R . .
C10 C 0.5176(6) 0.2386(3) 0.8468(2) 0.0521(10) Uani 1 1 d . . .
C11 C 0.5412(6) 0.3214(3) 0.8549(3) 0.0624(11) Uani 1 1 d . . .
H11 H 0.65 0.3469 0.8313 0.075 Uiso 1 1 calc R . .
C12 C 0.4020(6) 0.3656(3) 0.8980(3) 0.0663(12) Uani 1 1 d . . .
H12 H 0.4164 0.4213 0.9036 0.08 Uiso 1 1 calc R . .
C13 C 0.2405(6) 0.3275(3) 0.9331(3) 0.0605(11) Uani 1 1 d . . .
H13 H 0.1472 0.3577 0.9624 0.073 Uiso 1 1 calc R . .
N1 N -0.5251(5) 0.1098(2) 1.1152(2) 0.0571(9) Uani 1 1 d . . .
H1A H -0.425 0.0869 1.0923 0.068 Uiso 1 1 calc R . .
N2 N -0.2403(5) 0.19844(19) 1.0404(2) 0.0489(8) Uani 1 1 d . . .
N3 N -0.0940(4) 0.2414(2) 1.0015(2) 0.0493(8) Uani 1 1 d . . .
H3A H -0.0951 0.2935 1.0004 0.059 Uiso 1 1 calc R . .
O1 O 0.0521(4) 0.12431(17) 0.96593(19) 0.0633(8) Uani 1 1 d . . .
O2 O 0.0916(7) 0.3969(3) 1.2027(3) 0.1348(18) Uani 1 1 d . . .
O3 O 0.3413(8) 0.4429(3) 1.1214(4) 0.160(2) Uani 1 1 d . . .
O4 O 0.0771(9) 0.5210(3) 1.1439(3) 0.154(2) Uani 1 1 d . . .
O5 O 0.2798(8) 0.4991(4) 1.2537(3) 0.157(2) Uani 1 1 d . . .
O6 O -0.2532(5) 0.02399(19) 1.0300(2) 0.0868(11) Uani 1 1 d . . .
H61 H -0.1595 0.0544 1.0137 0.13 Uiso 1 1 d R . .
H62 H -0.2022 -0.0167 1.054 0.13 Uiso 1 1 d R . .
O7 O -0.1809(5) 0.40850(19) 1.0266(2) 0.0800(9) Uani 1 1 d . . .
H71 H -0.1454 0.4301 1.0726 0.12 Uiso 1 1 d R . .
H72 H -0.1783 0.4353 0.9803 0.12 Uiso 1 1 d R . .
Cl1 Cl 0.20073(18) 0.46403(7) 1.18157(8) 0.0676(3) Uani 1 1 d . . .
Br1 Br 0.71160(6) 0.17798(3) 0.78876(3) 0.0674(2) 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 0 '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 0.006 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
3 -4 5
0 -9 -3
2 2 -8
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
N1 C1 C2 119.8(5) . . ?
C3 C2 C1 119.3(5) . . ?
C2 C3 C4 119.8(5) . . ?
C3 C4 C5 120.5(5) . . ?
N1 C5 C4 118.0(4) . . ?
N1 C5 C6 119.2(3) . . ?
C4 C5 C6 122.7(4) . . ?
N2 C6 C5 117.9(4) . . ?
O1 C7 N3 121.3(4) . . ?
O1 C7 C8 121.1(4) . . ?
N3 C7 C8 117.6(4) . . ?
C13 C8 C9 119.2(4) . . ?
C13 C8 C7 123.8(4) . . ?
C9 C8 C7 116.9(4) . . ?
C10 C9 C8 119.8(4) . . ?
C9 C10 C11 120.9(4) . . ?
C9 C10 Br1 120.0(3) . . ?
C11 C10 Br1 119.0(3) . . ?
C12 C11 C10 119.2(4) . . ?
C11 C12 C13 120.3(4) . . ?
C8 C13 C12 120.5(4) . . ?
C1 N1 C5 122.6(4) . . ?
C6 N2 N3 118.3(3) . . ?
C7 N3 N2 117.0(3) . . ?
O5 Cl1 O2 111.1(4) . . ?
O5 Cl1 O3 112.5(4) . . ?
O2 Cl1 O3 109.6(3) . . ?
O5 Cl1 O4 107.2(4) . . ?
O2 Cl1 O4 108.4(4) . . ?
O3 Cl1 O4 108.0(4) . . ?
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
C1 N1 1.331(6) . ?
C1 C2 1.370(7) . ?
C2 C3 1.355(8) . ?
C3 C4 1.363(7) . ?
C4 C5 1.372(6) . ?
C5 N1 1.342(5) . ?
C5 C6 1.454(5) . ?
C6 N2 1.264(5) . ?
C7 O1 1.228(5) . ?
C7 N3 1.350(5) . ?
C7 C8 1.497(5) . ?
C8 C13 1.380(6) . ?
C8 C9 1.390(5) . ?
C9 C10 1.375(5) . ?
C10 C11 1.384(6) . ?
C10 Br1 1.891(4) . ?
C11 C12 1.374(6) . ?
C12 C13 1.384(6) . ?
N2 N3 1.368(4) . ?
O2 Cl1 1.377(4) . ?
O3 Cl1 1.386(5) . ?
O4 Cl1 1.393(5) . ?
O5 Cl1 1.370(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652689
