data_tba _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H16 Cl Fe N4 O3, C H4 O' _chemical_formula_sum 'C16 H20 Cl Fe N4 O4' _chemical_formula_weight 423.66 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' 'Cl' 'Cl' 0.1484 0.1585 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.493(2) _cell_length_b 6.9716(9) _cell_length_c 17.778(2) _cell_angle_alpha 90.00 _cell_angle_beta 116.838(3) _cell_angle_gamma 90.00 _cell_volume 1824.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 85(2) _cell_measurement_reflns_used 9347 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 36.32 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 1.003 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7529 _exptl_absorpt_correction_T_max 0.8977 _exptl_absorpt_process_details ? _exptl_special_details ; 5190 frames @ 5.055 cm; 0.5 deg. steps in omega, 0.45 deg. in phi ; _diffrn_ambient_temperature 85(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 108861 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 36.36 _reflns_number_total 8840 _reflns_number_gt 7927 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART-APEX' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0461P)^2^+0.5017P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8840 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0330 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0794 _refine_ls_wR_factor_gt 0.0760 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 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 0.721531(11) 0.36986(2) 0.635264(10) 0.01373(3) Uani 1 1 d . . . Fe1 Fe 0.785960(6) 0.200423(14) 0.558564(6) 0.01010(2) Uani 1 1 d . . . O1 O 0.91113(4) 0.30967(8) 0.63182(3) 0.01398(9) Uani 1 1 d . . . O2 O 1.05132(4) 0.34434(9) 0.73383(4) 0.01928(11) Uani 1 1 d . . . O3 O 0.68928(5) 0.47122(12) 0.42824(5) 0.03297(17) Uani 1 1 d . . . O4 O 1.08965(5) 0.70014(9) 0.69759(5) 0.02519(14) Uani 1 1 d . . . H4 H 1.0725(10) 0.607(2) 0.7057(9) 0.031(4) Uiso 1 1 d . . . N1 N 0.81541(4) -0.05015(8) 0.64402(3) 0.01094(9) Uani 1 1 d . . . N2 N 0.66571(4) 0.02038(9) 0.50052(4) 0.01246(10) Uani 1 1 d . . . N3 N 0.84865(4) 0.00635(9) 0.50654(4) 0.01191(9) Uani 1 1 d . . . N4 N 0.74558(4) 0.37350(9) 0.47583(4) 0.01587(11) Uani 1 1 d . . . C1 C 0.97873(5) 0.25349(10) 0.69943(4) 0.01311(11) Uani 1 1 d . . . C2 C 0.97414(5) 0.06394(11) 0.73986(5) 0.01572(12) Uani 1 1 d . . . H2A H 1.0168 0.0711 0.8007 0.019 Uiso 1 1 calc R . . H2B H 0.9964 -0.0385 0.7153 0.019 Uiso 1 1 calc R . . C3 C 0.88149(4) 0.00356(10) 0.73110(4) 0.01307(11) Uani 1 1 d . . . H3A H 0.8897 -0.1070 0.7688 0.016 Uiso 1 1 calc R . . H3B H 0.8558 0.1105 0.7502 0.016 Uiso 1 1 calc R . . C4 C 0.72742(4) -0.10112(10) 0.64283(4) 0.01199(10) Uani 1 1 d . . . H4A H 0.7121 -0.0060 0.6758 0.014 Uiso 1 1 calc R . . H4B H 0.7320 -0.2289 0.6688 0.014 Uiso 1 1 calc R . . C5 C 0.65437(4) -0.10362(10) 0.55308(4) 0.01234(11) Uani 1 1 d . . . C6 C 0.57916(5) -0.22379(11) 0.52601(5) 0.01584(12) Uani 1 1 d . . . H6A H 0.5727 -0.3106 0.5641 0.019 Uiso 1 1 calc R . . C7 C 0.51362(5) -0.21516(11) 0.44238(5) 0.01870(14) Uani 1 1 d . . . H7A H 0.4610 -0.2939 0.4227 0.022 Uiso 1 1 calc R . . C8 C 0.52637(5) -0.08923(12) 0.38789(5) 0.01846(13) Uani 1 1 d . . . H8A H 0.4831 -0.0822 0.3302 0.022 Uiso 1 1 calc R . . C9 C 0.60319(5) 0.02563(11) 0.41910(4) 0.01517(12) Uani 1 1 d . . . H9A H 0.6120 0.1110 0.3818 0.018 Uiso 1 1 calc R . . C10 C 0.84795(5) -0.21665(10) 0.61242(4) 0.01356(11) Uani 1 1 d . . . H10A H 0.8009 -0.3181 0.5938 0.016 Uiso 1 1 calc R . . H10B H 0.9033 -0.2692 0.6596 0.016 Uiso 1 1 calc R . . C11 C 0.86916(4) -0.16937(10) 0.54049(4) 0.01148(10) Uani 1 1 d . . . C12 C 0.90617(5) -0.30980(10) 0.50919(5) 0.01414(11) Uani 1 1 d . . . H12A H 0.9206 -0.4332 0.5345 0.017 Uiso 1 1 calc R . . C13 C 0.92160(5) -0.26659(12) 0.44070(5) 0.01713(12) Uani 1 1 d . . . H13A H 0.9449 -0.3612 0.4172 0.021 Uiso 1 1 calc R . . C14 C 0.90236(5) -0.08224(12) 0.40671(5) 0.01672(12) Uani 1 1 d . . . H14A H 0.9137 -0.0481 0.3606 0.020 Uiso 1 1 calc R . . C15 C 0.86644(5) 0.04971(11) 0.44143(4) 0.01417(11) Uani 1 1 d . . . H15A H 0.8538 0.1757 0.4187 0.017 Uiso 1 1 calc R . . C16 C 1.17946(6) 0.72026(15) 0.76245(6) 0.02733(18) Uani 1 1 d . . . H16A H 1.1840 0.6618 0.8144 0.041 Uiso 1 1 calc R . . H16B H 1.1949 0.8567 0.7722 0.041 Uiso 1 1 calc R . . H16C H 1.2217 0.6562 0.7457 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01612(6) 0.01131(6) 0.01642(6) -0.00138(5) 0.00968(5) 0.00002(5) Fe1 0.01187(4) 0.00875(4) 0.01028(4) 0.00040(3) 0.00553(3) -0.00018(3) O1 0.01376(19) 0.0129(2) 0.0144(2) 0.00104(15) 0.00553(16) -0.00134(16) O2 0.0182(2) 0.0217(3) 0.0152(2) -0.00122(19) 0.00513(18) -0.0079(2) O3 0.0271(3) 0.0315(4) 0.0311(3) 0.0161(3) 0.0049(3) 0.0038(3) O4 0.0213(3) 0.0179(3) 0.0276(3) 0.0051(2) 0.0033(2) -0.0002(2) N1 0.01267(19) 0.0107(2) 0.01083(19) -0.00001(16) 0.00651(16) -0.00011(17) N2 0.0134(2) 0.0121(2) 0.0116(2) -0.00036(17) 0.00546(17) -0.00068(17) N3 0.0139(2) 0.0111(2) 0.0121(2) 0.00053(17) 0.00704(17) -0.00019(17) N4 0.0183(2) 0.0129(2) 0.0170(2) 0.00042(19) 0.0083(2) -0.00146(19) C1 0.0143(2) 0.0144(3) 0.0119(2) -0.0013(2) 0.00708(19) -0.0014(2) C2 0.0130(2) 0.0169(3) 0.0159(3) 0.0037(2) 0.0054(2) -0.0005(2) C3 0.0134(2) 0.0152(3) 0.0105(2) 0.00125(19) 0.00526(19) -0.0008(2) C4 0.0129(2) 0.0122(2) 0.0121(2) 0.00064(19) 0.00671(19) -0.00115(19) C5 0.0130(2) 0.0113(2) 0.0132(2) -0.00054(19) 0.00634(19) -0.00087(19) C6 0.0150(2) 0.0136(3) 0.0186(3) -0.0008(2) 0.0073(2) -0.0030(2) C7 0.0159(3) 0.0172(3) 0.0198(3) -0.0037(2) 0.0053(2) -0.0047(2) C8 0.0163(3) 0.0188(3) 0.0157(3) -0.0029(2) 0.0032(2) -0.0027(2) C9 0.0157(2) 0.0156(3) 0.0124(2) -0.0006(2) 0.0047(2) -0.0008(2) C10 0.0188(2) 0.0099(2) 0.0157(2) 0.00152(19) 0.0111(2) 0.0016(2) C11 0.0119(2) 0.0115(2) 0.0119(2) -0.00019(18) 0.00622(18) -0.00029(19) C12 0.0152(2) 0.0134(3) 0.0159(3) 0.0000(2) 0.0089(2) 0.0021(2) C13 0.0186(3) 0.0192(3) 0.0168(3) 0.0003(2) 0.0107(2) 0.0042(2) C14 0.0180(3) 0.0207(3) 0.0146(3) 0.0015(2) 0.0100(2) 0.0030(2) C15 0.0163(2) 0.0149(3) 0.0136(2) 0.0017(2) 0.0087(2) 0.0008(2) C16 0.0223(3) 0.0296(4) 0.0244(4) 0.0039(3) 0.0056(3) -0.0046(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Fe1 2.3858(3) . ? Fe1 N4 1.7828(7) . ? Fe1 O1 2.0274(6) . ? Fe1 N3 2.1491(6) . ? Fe1 N2 2.1739(6) . ? Fe1 N1 2.2202(6) . ? O1 C1 1.2772(8) . ? O2 C1 1.2439(9) . ? O3 N4 1.1545(9) . ? O4 C16 1.4147(11) . ? N1 C3 1.4837(9) . ? N1 C4 1.4850(9) . ? N1 C10 1.4911(9) . ? N2 C9 1.3462(9) . ? N2 C5 1.3465(9) . ? N3 C11 1.3399(9) . ? N3 C15 1.3506(9) . ? C1 C2 1.5225(11) . ? C2 C3 1.5237(10) . ? C4 C5 1.5040(9) . ? C5 C6 1.3904(10) . ? C6 C7 1.3898(11) . ? C7 C8 1.3919(12) . ? C8 C9 1.3855(11) . ? C10 C11 1.5065(10) . ? C11 C12 1.3956(10) . ? C12 C13 1.3848(11) . ? C13 C14 1.3945(11) . ? C14 C15 1.3815(11) . ? 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 N4 Fe1 O1 99.70(3) . . ? N4 Fe1 N3 98.29(3) . . ? O1 Fe1 N3 87.98(2) . . ? N4 Fe1 N2 94.49(3) . . ? O1 Fe1 N2 165.47(2) . . ? N3 Fe1 N2 86.86(2) . . ? N4 Fe1 N1 169.08(3) . . ? O1 Fe1 N1 90.65(2) . . ? N3 Fe1 N1 78.46(2) . . ? N2 Fe1 N1 75.01(2) . . ? N4 Fe1 Cl1 92.27(2) . . ? O1 Fe1 Cl1 91.946(19) . . ? N3 Fe1 Cl1 169.307(17) . . ? N2 Fe1 Cl1 90.623(19) . . ? N1 Fe1 Cl1 90.847(18) . . ? C1 O1 Fe1 133.83(5) . . ? C3 N1 C4 109.14(5) . . ? C3 N1 C10 111.70(5) . . ? C4 N1 C10 108.91(5) . . ? C3 N1 Fe1 110.25(4) . . ? C4 N1 Fe1 105.55(4) . . ? C10 N1 Fe1 111.07(4) . . ? C9 N2 C5 118.99(6) . . ? C9 N2 Fe1 125.91(5) . . ? C5 N2 Fe1 115.09(4) . . ? C11 N3 C15 118.85(6) . . ? C11 N3 Fe1 117.02(5) . . ? C15 N3 Fe1 124.11(5) . . ? O3 N4 Fe1 151.80(7) . . ? O2 C1 O1 122.97(7) . . ? O2 C1 C2 116.86(6) . . ? O1 C1 C2 120.13(6) . . ? C1 C2 C3 116.94(6) . . ? N1 C3 C2 113.99(6) . . ? N1 C4 C5 109.11(5) . . ? N2 C5 C6 121.90(6) . . ? N2 C5 C4 115.66(6) . . ? C6 C5 C4 122.43(6) . . ? C7 C6 C5 119.06(7) . . ? C6 C7 C8 118.88(7) . . ? C9 C8 C7 118.95(7) . . ? N2 C9 C8 122.20(7) . . ? N1 C10 C11 114.23(6) . . ? N3 C11 C12 121.91(6) . . ? N3 C11 C10 118.32(6) . . ? C12 C11 C10 119.73(6) . . ? C13 C12 C11 119.02(7) . . ? C12 C13 C14 119.04(7) . . ? C15 C14 C13 118.66(7) . . ? N3 C15 C14 122.47(7) . . ? 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 O4 H4 O2 0.747(16) 1.971(16) 2.7084(10) 169.0(16) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 36.36 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.028 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.077