#------------------------------------------------------------------------------
#$Date: 2018-09-24 09:49:13 +0300 (Mon, 24 Sep 2018) $
#$Revision: 211137 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/40/1544020.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_1544020
loop_
_publ_author_name
'Wang Jing-lin'
'Zhao Ya-qin'
'Yang Bin-sheng'
_publ_section_title
;
 Transition metal complexes of asymmetrical aroyl-hydrazone ligand:
 Syntheses, structures, DNA binding and cleavage studies
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              484
_journal_page_last               496
_journal_paper_doi               10.1016/j.ica.2013.09.001
_journal_volume                  409B
_journal_year                    2014
_chemical_formula_sum            'C15 H19 Cl2 Fe N4 O6'
_chemical_formula_weight         478.09
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 103.019(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8267(12)
_cell_length_b                   22.497(3)
_cell_length_c                   8.5677(10)
_cell_measurement_reflns_used    2472
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.191
_cell_measurement_theta_min      2.603
_cell_volume                     2033.2(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            10158
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    1.043
_exptl_absorpt_correction_T_max  0.7953
_exptl_absorpt_correction_T_min  0.6289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            dark
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0411
_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)+(0.0381P)²+1.1631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                2381
_reflns_number_total             3588
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2014-409B-484-496-4.cif
_cod_data_source_block           090105d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 4624 2016-04-14 12:54:50Z antanas 

The following automatic conversions were performed:

'_journal_paper_doi' value
'http://dx.doi.org/10.1016/j.ica.2013.09.001' was changed to
'10.1016/j.ica.2013.09.001'.

Automatic conversion script
Id: cif_fix_values 6433 2018-09-21 13:16:33Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1544020
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
Fe1 Fe 0.66249(5) 0.61517(2) 0.38703(6) 0.03332(17) Uani 1 1 d . . .
Cl1 Cl 0.81683(10) 0.64285(5) 0.26233(14) 0.0571(3) Uani 1 1 d . . .
Cl2 Cl 0.61616(10) 0.52807(4) 0.23321(12) 0.0488(3) Uani 1 1 d . . .
N1 N 0.8984(3) 0.47311(13) 0.7928(4) 0.0413(8) Uani 1 1 d . . .
N2 N 0.8161(4) 0.39124(16) 1.1115(4) 0.0567(10) Uani 1 1 d . . .
N3 N 0.5936(3) 0.54738(12) 0.6510(4) 0.0370(8) Uani 1 1 d . . .
H3 H 0.5518 0.5304 0.7130 0.044 Uiso 1 1 calc R . .
N4 N 0.5374(3) 0.58728(12) 0.5338(3) 0.0295(7) Uani 1 1 d . . .
O1 O 0.7732(2) 0.56312(11) 0.5709(3) 0.0405(6) Uani 1 1 d . . .
O2 O 0.7150(4) 0.38782(14) 1.1514(4) 0.0762(10) Uani 1 1 d . . .
O3 O 0.9097(4) 0.36340(18) 1.1742(5) 0.1022(14) Uani 1 1 d . . .
O4 O 0.5218(2) 0.66158(10) 0.2803(3) 0.0361(6) Uani 1 1 d . . .
O5 O 0.7138(2) 0.68366(11) 0.5522(3) 0.0490(7) Uani 1 1 d . . .
H5 H 0.6698 0.7137 0.5374 0.074 Uiso 1 1 d R . .
O6 O 0.5749(3) 0.72153(12) 1.0145(3) 0.0549(8) Uani 1 1 d . . .
H6 H 0.5782 0.7037 1.0988 0.082 Uiso 1 1 calc R . .
C1 C 0.7164(4) 0.53671(15) 0.6623(4) 0.0332(9) Uani 1 1 d . . .
C2 C 0.7768(4) 0.49434(15) 0.7820(4) 0.0339(9) Uani 1 1 d . . .
C3 C 0.7291(4) 0.46700(16) 0.9001(4) 0.0401(10) Uani 1 1 d . . .
H3A H 0.6498 0.4730 0.9223 0.048 Uiso 1 1 calc R . .
C4 C 0.8230(4) 0.42883(16) 0.9788(5) 0.0427(10) Uani 1 1 d . . .
C5 C 0.9264(4) 0.43358(17) 0.9121(5) 0.0507(11) Uani 1 1 d . . .
H5A H 1.0024 0.4130 0.9442 0.061 Uiso 1 1 calc R . .
C6 C 0.9840(4) 0.48677(19) 0.6875(6) 0.0651(14) Uani 1 1 d . . .
H6A H 1.0656 0.4695 0.7307 0.098 Uiso 1 1 calc R . .
H6B H 0.9924 0.5291 0.6798 0.098 Uiso 1 1 calc R . .
H6C H 0.9500 0.4706 0.5829 0.098 Uiso 1 1 calc R . .
C7 C 0.4225(3) 0.60264(14) 0.5297(4) 0.0329(9) Uani 1 1 d . . .
H7 H 0.3824 0.5865 0.6051 0.039 Uiso 1 1 calc R . .
C8 C 0.3531(3) 0.64351(15) 0.4142(4) 0.0304(8) Uani 1 1 d . . .
C9 C 0.4038(3) 0.67093(15) 0.2949(4) 0.0311(8) Uani 1 1 d . . .
C10 C 0.3269(4) 0.71015(17) 0.1899(5) 0.0443(10) Uani 1 1 d . . .
H10 H 0.3583 0.7288 0.1100 0.053 Uiso 1 1 calc R . .
C11 C 0.2051(4) 0.72141(18) 0.2037(5) 0.0497(11) Uani 1 1 d . . .
H11 H 0.1559 0.7481 0.1330 0.060 Uiso 1 1 calc R . .
C12 C 0.1532(4) 0.69442(18) 0.3194(5) 0.0480(11) Uani 1 1 d . . .
H12 H 0.0702 0.7022 0.3262 0.058 Uiso 1 1 calc R . .
C13 C 0.2283(4) 0.65587(16) 0.4235(5) 0.0400(9) Uani 1 1 d . . .
H13 H 0.1953 0.6375 0.5025 0.048 Uiso 1 1 calc R . .
C14 C 0.8390(4) 0.6987(2) 0.6373(7) 0.0825(17) Uani 1 1 d . . .
H14A H 0.8742 0.7276 0.5773 0.124 Uiso 1 1 calc R . .
H14B H 0.8910 0.6636 0.6516 0.124 Uiso 1 1 calc R . .
H14C H 0.8360 0.7148 0.7401 0.124 Uiso 1 1 calc R . .
C15 C 0.5772(6) 0.6806(2) 0.8921(6) 0.0897(18) Uani 1 1 d . . .
H15A H 0.6632 0.6746 0.8833 0.135 Uiso 1 1 calc R . .
H15B H 0.5281 0.6957 0.7925 0.135 Uiso 1 1 calc R . .
H15C H 0.5421 0.6435 0.9166 0.135 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'
Fe Fe 0.3463 0.8444 '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'
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
O4 Fe1 O5 88.99(10) . .
O4 Fe1 O1 157.45(10) . .
O5 Fe1 O1 83.31(10) . .
O4 Fe1 N4 84.20(10) . .
O5 Fe1 N4 85.68(11) . .
O1 Fe1 N4 74.13(10) . .
O4 Fe1 Cl1 102.62(8) . .
O5 Fe1 Cl1 90.29(8) . .
O1 Fe1 Cl1 98.60(8) . .
N4 Fe1 Cl1 172.04(8) . .
O4 Fe1 Cl2 98.13(8) . .
O5 Fe1 Cl2 171.33(8) . .
O1 Fe1 Cl2 88.25(8) . .
N4 Fe1 Cl2 90.10(8) . .
Cl1 Fe1 Cl2 92.96(4) . .
C5 N1 C2 109.2(3) . .
C5 N1 C6 123.0(3) . .
C2 N1 C6 127.7(3) . .
O3 N2 O2 123.9(4) . .
O3 N2 C4 118.0(4) . .
O2 N2 C4 118.1(4) . .
C1 N3 N4 116.0(3) . .
C1 N3 H3 122.0 . .
N4 N3 H3 122.0 . .
C7 N4 N3 117.4(3) . .
C7 N4 Fe1 130.0(2) . .
N3 N4 Fe1 112.6(2) . .
C1 O1 Fe1 117.1(2) . .
C9 O4 Fe1 136.5(2) . .
C14 O5 Fe1 126.8(3) . .
C14 O5 H5 109.6 . .
Fe1 O5 H5 116.6 . .
C15 O6 H6 109.5 . .
O1 C1 N3 119.5(3) . .
O1 C1 C2 123.4(3) . .
N3 C1 C2 117.0(3) . .
C3 C2 N1 107.7(3) . .
C3 C2 C1 129.1(4) . .
N1 C2 C1 123.1(3) . .
C2 C3 C4 106.2(4) . .
C2 C3 H3A 126.9 . .
C4 C3 H3A 126.9 . .
C5 C4 C3 109.1(3) . .
C5 C4 N2 124.8(4) . .
C3 C4 N2 126.0(4) . .
N1 C5 C4 107.7(4) . .
N1 C5 H5A 126.1 . .
C4 C5 H5A 126.1 . .
N1 C6 H6A 109.5 . .
N1 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
N1 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N4 C7 C8 123.1(3) . .
N4 C7 H7 118.5 . .
C8 C7 H7 118.5 . .
C13 C8 C9 119.6(3) . .
C13 C8 C7 116.8(3) . .
C9 C8 C7 123.6(3) . .
O4 C9 C10 119.1(3) . .
O4 C9 C8 122.7(3) . .
C10 C9 C8 118.2(3) . .
C11 C10 C9 120.4(4) . .
C11 C10 H10 119.8 . .
C9 C10 H10 119.8 . .
C10 C11 C12 122.2(4) . .
C10 C11 H11 118.9 . .
C12 C11 H11 118.9 . .
C13 C12 C11 117.8(4) . .
C13 C12 H12 121.1 . .
C11 C12 H12 121.1 . .
C12 C13 C8 121.8(4) . .
C12 C13 H13 119.1 . .
C8 C13 H13 119.1 . .
O5 C14 H14A 109.5 . .
O5 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
O5 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
O6 C15 H15A 109.5 . .
O6 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
O6 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 O4 1.902(2) .
Fe1 O5 2.081(3) .
Fe1 O1 2.107(2) .
Fe1 N4 2.140(3) .
Fe1 Cl1 2.2640(11) .
Fe1 Cl2 2.3516(11) .
N1 C5 1.338(5) .
N1 C2 1.383(5) .
N1 C6 1.464(5) .
N2 O3 1.209(4) .
N2 O2 1.220(5) .
N2 C4 1.433(5) .
N3 C1 1.333(5) .
N3 N4 1.382(4) .
N3 H3 0.8600 .
N4 C7 1.284(4) .
O1 C1 1.250(4) .
O4 C9 1.328(4) .
O5 C14 1.428(5) .
O5 H5 0.8200 .
O6 C15 1.400(5) .
O6 H6 0.8200 .
C1 C2 1.445(5) .
C2 C3 1.379(5) .
C3 C4 1.385(5) .
C3 H3A 0.9300 .
C4 C5 1.370(6) .
C5 H5A 0.9300 .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 C8 1.433(5) .
C7 H7 0.9300 .
C8 C13 1.399(5) .
C8 C9 1.407(5) .
C9 C10 1.394(5) .
C10 C11 1.373(5) .
C10 H10 0.9300 .
C11 C12 1.385(6) .
C11 H11 0.9300 .
C12 C13 1.372(5) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
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
C1 N3 N4 C7 -173.7(3) . . . .
C1 N3 N4 Fe1 5.2(4) . . . .
O4 Fe1 N4 C7 -1.2(3) . . . .
O5 Fe1 N4 C7 88.2(3) . . . .
O1 Fe1 N4 C7 172.5(3) . . . .
Cl1 Fe1 N4 C7 148.0(5) . . . .
Cl2 Fe1 N4 C7 -99.3(3) . . . .
O4 Fe1 N4 N3 180.0(2) . . . .
O5 Fe1 N4 N3 -90.6(2) . . . .
O1 Fe1 N4 N3 -6.3(2) . . . .
Cl1 Fe1 N4 N3 -30.8(7) . . . .
Cl2 Fe1 N4 N3 81.8(2) . . . .
O4 Fe1 O1 C1 23.9(4) . . . .
O5 Fe1 O1 C1 94.7(3) . . . .
N4 Fe1 O1 C1 7.3(2) . . . .
Cl1 Fe1 O1 C1 -176.0(2) . . . .
Cl2 Fe1 O1 C1 -83.3(2) . . . .
O5 Fe1 O4 C9 -85.6(3) . . . .
O1 Fe1 O4 C9 -15.8(5) . . . .
N4 Fe1 O4 C9 0.2(3) . . . .
Cl1 Fe1 O4 C9 -175.6(3) . . . .
Cl2 Fe1 O4 C9 89.5(3) . . . .
O4 Fe1 O5 C14 -149.8(4) . . . .
O1 Fe1 O5 C14 51.4(4) . . . .
N4 Fe1 O5 C14 125.9(4) . . . .
Cl1 Fe1 O5 C14 -47.2(4) . . . .
Cl2 Fe1 O5 C14 64.9(7) . . . .
Fe1 O1 C1 N3 -7.1(4) . . . .
Fe1 O1 C1 C2 172.9(2) . . . .
N4 N3 C1 O1 1.0(5) . . . .
N4 N3 C1 C2 -178.9(3) . . . .
C5 N1 C2 C3 0.4(4) . . . .
C6 N1 C2 C3 176.4(4) . . . .
C5 N1 C2 C1 -178.4(3) . . . .
C6 N1 C2 C1 -2.3(6) . . . .
O1 C1 C2 C3 172.6(4) . . . .
N3 C1 C2 C3 -7.4(6) . . . .
O1 C1 C2 N1 -8.9(5) . . . .
N3 C1 C2 N1 171.1(3) . . . .
N1 C2 C3 C4 -0.9(4) . . . .
C1 C2 C3 C4 177.8(3) . . . .
C2 C3 C4 C5 1.0(4) . . . .
C2 C3 C4 N2 179.5(4) . . . .
O3 N2 C4 C5 3.2(6) . . . .
O2 N2 C4 C5 -174.6(4) . . . .
O3 N2 C4 C3 -175.0(4) . . . .
O2 N2 C4 C3 7.2(6) . . . .
C2 N1 C5 C4 0.3(4) . . . .
C6 N1 C5 C4 -176.0(4) . . . .
C3 C4 C5 N1 -0.8(5) . . . .
N2 C4 C5 N1 -179.3(3) . . . .
N3 N4 C7 C8 -179.9(3) . . . .
Fe1 N4 C7 C8 1.4(5) . . . .
N4 C7 C8 C13 179.7(3) . . . .
N4 C7 C8 C9 -0.2(5) . . . .
Fe1 O4 C9 C10 179.5(3) . . . .
Fe1 O4 C9 C8 0.6(5) . . . .
C13 C8 C9 O4 179.3(3) . . . .
C7 C8 C9 O4 -0.8(5) . . . .
C13 C8 C9 C10 0.4(5) . . . .
C7 C8 C9 C10 -179.7(3) . . . .
O4 C9 C10 C11 -179.0(3) . . . .
C8 C9 C10 C11 0.0(5) . . . .
C9 C10 C11 C12 -0.7(6) . . . .
C10 C11 C12 C13 0.8(6) . . . .
C11 C12 C13 C8 -0.4(6) . . . .
C9 C8 C13 C12 -0.2(5) . . . .
C7 C8 C13 C12 179.9(3) . . . .
