data_shelxl
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             hya4
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C21 H20 Cl Fe N5 O2'
_chemical_formula_weight          465.72
 
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                    8.6726(6)
_cell_length_b                    12.8597(8)
_cell_length_c                    19.4545(12)
_cell_angle_alpha                 90.00
_cell_angle_beta                  92.648(4)
_cell_angle_gamma                 90.00
_cell_volume                      2167.4(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     8249
_cell_measurement_theta_min       2.53
_cell_measurement_theta_max       25.35
 
_exptl_crystal_description        block
_exptl_crystal_colour             orange
_exptl_crystal_size_max           8.00
_exptl_crystal_size_mid           5.00
_exptl_crystal_size_min           2.00
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.427
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              960
_exptl_absorpt_coefficient_mu     0.846
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.0564
_exptl_absorpt_correction_T_max   0.2824
_exptl_absorpt_process_details    SADABS
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'microfocus sealed tube'
_diffrn_radiation_monochromator   'QUAZAR multilayer mirrors'
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        '\f and \w scans'
_diffrn_detector_area_resol_mean  8.366
_diffrn_reflns_number             21054
_diffrn_reflns_av_R_equivalents   0.0603
_diffrn_reflns_av_sigmaI/netI     0.0634
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -23
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          1.90
_diffrn_reflns_theta_max          25.47
_reflns_number_total              3991
_reflns_number_gt                 2868
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     SIR-2004
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     ORTEP-32
_computing_publication_material   WINGX
 
_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^)+(0.1061P)^2^+7.1575P] 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     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          3991
_refine_ls_number_parameters      257
_refine_ls_number_restraints      257
_refine_ls_R_factor_all           0.1044
_refine_ls_R_factor_gt            0.0715
_refine_ls_wR_factor_ref          0.2031
_refine_ls_wR_factor_gt           0.1842
_refine_ls_goodness_of_fit_ref    1.033
_refine_ls_restrained_S_all       1.005
_refine_ls_shift/su_max           0.014
_refine_ls_shift/su_mean          0.001
 
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 0.3368(8) 0.3138(5) 0.6835(3) 0.0419(14) Uani 1 1 d U . .
H1 H 0.3069 0.3865 0.6953 0.050 Uiso 1 1 calc R . .
C2 C 0.4794(8) 0.2792(5) 0.7251(3) 0.0431(14) Uani 1 1 d U . .
C3 C 0.5819(9) 0.3467(7) 0.7579(3) 0.0629(19) Uani 1 1 d U . .
H3 H 0.5640 0.4196 0.7571 0.075 Uiso 1 1 calc R . .
C4 C 0.7115(9) 0.3058(8) 0.7921(4) 0.074(2) Uani 1 1 d U . .
H4 H 0.7830 0.3514 0.8150 0.089 Uiso 1 1 calc R . .
C5 C 0.7386(8) 0.2021(8) 0.7935(3) 0.066(2) Uani 1 1 d U . .
H5 H 0.8280 0.1744 0.8170 0.080 Uiso 1 1 calc R . .
C6 C 0.6305(7) 0.1366(7) 0.7592(3) 0.0519(17) Uani 1 1 d U . .
H6 H 0.6474 0.0636 0.7600 0.062 Uiso 1 1 calc R . .
C7 C 0.3721(9) 0.3039(4) 0.6078(3) 0.0456(16) Uani 1 1 d U . .
C8 C 0.3909(12) 0.3886(5) 0.5652(3) 0.071(3) Uani 1 1 d U . .
H8 H 0.3815 0.4576 0.5821 0.085 Uiso 1 1 calc R . .
C9 C 0.4243(11) 0.3699(6) 0.4967(4) 0.069(2) Uani 1 1 d U . .
H9 H 0.4316 0.4259 0.4652 0.083 Uiso 1 1 calc R . .
C10 C 0.4464(10) 0.2693(5) 0.4755(3) 0.056(2) Uani 1 1 d U . .
H10 H 0.4786 0.2554 0.4304 0.067 Uiso 1 1 calc R . .
C11 C 0.4215(7) 0.1888(4) 0.5203(2) 0.0316(13) Uani 1 1 d U . .
H11 H 0.4326 0.1193 0.5047 0.038 Uiso 1 1 calc R . .
C12 C 0.0688(7) 0.2563(5) 0.6510(3) 0.0457(14) Uani 1 1 d U . .
H12A H -0.0078 0.2953 0.6771 0.055 Uiso 1 1 calc R . .
H12B H 0.0948 0.2992 0.6109 0.055 Uiso 1 1 calc R . .
C13 C -0.0012(7) 0.1588(6) 0.6262(3) 0.0425(14) Uani 1 1 d U . .
C14 C -0.1650(8) 0.1503(7) 0.6056(3) 0.0619(19) Uani 1 1 d U . .
H14 H -0.2320 0.2078 0.6111 0.074 Uiso 1 1 calc R . .
C15 C -0.2187(10) 0.0628(9) 0.5793(4) 0.075(2) Uani 1 1 d U . .
H15 H -0.3245 0.0580 0.5647 0.090 Uiso 1 1 calc R . .
C16 C -0.1235(9) -0.0225(7) 0.5727(4) 0.067(2) Uani 1 1 d U . .
H16 H -0.1622 -0.0863 0.5542 0.080 Uiso 1 1 calc R . .
C17 C 0.0305(8) -0.0115(6) 0.5939(3) 0.0481(16) Uani 1 1 d U . .
H17 H 0.0971 -0.0696 0.5900 0.058 Uiso 1 1 calc R . .
C18 C 0.1780(7) 0.2319(4) 0.7700(2) 0.0312(12) Uani 1 1 d U . .
H18A H 0.0807 0.2696 0.7775 0.037 Uiso 1 1 calc R . .
H18B H 0.2612 0.2657 0.7985 0.037 Uiso 1 1 calc R . .
C19 C 0.1611(6) 0.1192(4) 0.7935(2) 0.0289(12) Uani 1 1 d U . .
C101 C 0.4425(16) 0.1511(10) 0.9393(7) 0.132(4) Uiso 1 1 d U . .
H10A H 0.3834 0.1381 0.9802 0.198 Uiso 1 1 calc R . .
H10B H 0.3722 0.1726 0.9011 0.198 Uiso 1 1 calc R . .
H10C H 0.5182 0.2063 0.9493 0.198 Uiso 1 1 calc R . .
C102 C 0.5218(18) 0.0572(12) 0.9208(8) 0.136(5) Uiso 1 1 d U . .
N1 N 0.2141(6) 0.2403(4) 0.6969(2) 0.0336(10) Uani 1 1 d U . .
N2 N 0.5066(5) 0.1733(4) 0.7260(2) 0.0363(11) Uani 1 1 d U . .
N3 N 0.3816(5) 0.2054(3) 0.5857(2) 0.0285(10) Uani 1 1 d U . .
N4 N 0.0899(5) 0.0782(4) 0.6198(2) 0.0374(11) Uani 1 1 d U . .
N101 N 0.6048(18) -0.0305(13) 0.9170(8) 0.185(6) Uiso 1 1 d U . .
O1 O 0.2219(4) 0.0487(3) 0.75763(16) 0.0302(9) Uani 1 1 d U . .
O2 O 0.0941(5) 0.1045(3) 0.84738(19) 0.0458(11) Uani 1 1 d U . .
Cl1 Cl 0.43355(19) -0.05552(11) 0.62195(7) 0.0406(4) Uani 1 1 d U . .
Fe1 Fe 0.32218(8) 0.09191(5) 0.66470(3) 0.0199(2) Uani 1 1 d U . .
 
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
C1 0.066(4) 0.029(3) 0.032(3) -0.008(2) 0.012(3) -0.004(3)
C2 0.057(4) 0.046(3) 0.029(3) -0.020(2) 0.023(2) -0.029(3)
C3 0.063(4) 0.076(5) 0.052(4) -0.035(3) 0.023(3) -0.033(4)
C4 0.054(4) 0.115(6) 0.055(4) -0.054(5) 0.017(3) -0.029(4)
C5 0.036(4) 0.121(6) 0.043(4) -0.042(4) 0.010(3) -0.009(4)
C6 0.032(3) 0.090(5) 0.034(3) -0.018(3) 0.007(2) -0.003(3)
C7 0.084(5) 0.023(3) 0.032(3) -0.002(2) 0.021(3) -0.006(3)
C8 0.141(8) 0.029(4) 0.045(3) -0.004(3) 0.037(4) -0.007(4)
C9 0.129(7) 0.036(3) 0.045(3) 0.005(3) 0.040(4) -0.012(4)
C10 0.105(6) 0.035(3) 0.030(3) -0.002(2) 0.034(3) -0.005(4)
C11 0.050(4) 0.026(3) 0.019(2) -0.005(2) 0.009(2) 0.003(3)
C12 0.048(3) 0.054(4) 0.035(3) 0.009(3) 0.006(3) 0.030(3)
C13 0.039(3) 0.067(4) 0.021(2) 0.004(3) 0.006(2) 0.010(3)
C14 0.038(4) 0.103(6) 0.045(4) 0.018(4) 0.009(3) 0.013(4)
C15 0.040(4) 0.127(7) 0.058(4) 0.011(5) -0.006(4) -0.017(4)
C16 0.055(4) 0.096(6) 0.048(4) 0.013(4) -0.011(3) -0.037(4)
C17 0.046(4) 0.066(4) 0.031(3) 0.003(3) -0.001(3) -0.025(3)
C18 0.039(3) 0.034(3) 0.021(2) -0.004(2) 0.012(2) 0.008(3)
C19 0.030(3) 0.036(3) 0.021(2) -0.001(2) 0.005(2) 0.002(2)
N1 0.049(3) 0.029(2) 0.024(2) 0.0008(18) 0.0106(19) 0.010(2)
N2 0.027(2) 0.060(3) 0.023(2) -0.009(2) 0.0068(18) -0.007(2)
N3 0.041(3) 0.026(2) 0.0189(18) -0.0016(16) 0.0044(18) -0.006(2)
N4 0.026(2) 0.063(3) 0.024(2) 0.000(2) 0.0045(18) -0.005(2)
O1 0.038(2) 0.031(2) 0.0222(16) 0.0018(15) 0.0096(15) -0.0023(17)
O2 0.063(3) 0.046(3) 0.030(2) 0.0030(17) 0.026(2) 0.004(2)
Cl1 0.0599(10) 0.0271(8) 0.0362(7) -0.0012(6) 0.0172(7) 0.0088(7)
Fe1 0.0211(4) 0.0214(4) 0.0173(4) -0.0021(3) 0.0037(3) 0.0001(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
C1 N1 1.456(8) . ?
C1 C2 1.513(10) . ?
C1 C7 1.524(7) . ?
C1 H1 1.0000 . ?
C2 C3 1.378(9) . ?
C2 N2 1.383(8) . ?
C3 C4 1.383(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.354(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(10) . ?
C5 H5 0.9500 . ?
C6 N2 1.315(8) . ?
C6 H6 0.9500 . ?
C7 N3 1.341(7) . ?
C7 C8 1.382(9) . ?
C8 C9 1.398(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.374(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(8) . ?
C10 H10 0.9500 . ?
C11 N3 1.351(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.465(10) . ?
C12 N1 1.525(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N4 1.312(8) . ?
C13 C14 1.462(9) . ?
C14 C15 1.313(12) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(10) . ?
C16 H16 0.9500 . ?
C17 N4 1.351(8) . ?
C17 H17 0.9500 . ?
C18 N1 1.473(6) . ?
C18 C19 1.529(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O2 1.236(6) . ?
C19 O1 1.273(6) . ?
C101 C102 1.443(18) . ?
C101 H10A 0.9800 . ?
C101 H10B 0.9800 . ?
C101 H10C 0.9800 . ?
C102 N101 1.343(18) . ?
N1 Fe1 2.229(4) . ?
N2 Fe1 2.214(5) . ?
N3 Fe1 2.198(4) . ?
N4 Fe1 2.166(5) . ?
O1 Fe1 2.116(3) . ?
Cl1 Fe1 2.3007(15) . ?
 
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 107.4(5) . . ?
N1 C1 C7 107.5(5) . . ?
C2 C1 C7 107.3(5) . . ?
N1 C1 H1 111.5 . . ?
C2 C1 H1 111.5 . . ?
C7 C1 H1 111.5 . . ?
C3 C2 N2 120.6(7) . . ?
C3 C2 C1 123.8(7) . . ?
N2 C2 C1 115.5(5) . . ?
C2 C3 C4 118.4(8) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 121.5(7) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 117.9(8) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
N2 C6 C5 122.0(8) . . ?
N2 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
N3 C7 C8 122.8(5) . . ?
N3 C7 C1 114.0(5) . . ?
C8 C7 C1 123.2(5) . . ?
C7 C8 C9 118.0(6) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 H8 121.0 . . ?
C10 C9 C8 119.1(6) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 119.3(5) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
N3 C11 C10 122.1(5) . . ?
N3 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C13 C12 N1 113.3(5) . . ?
C13 C12 H12A 108.9 . . ?
N1 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
N1 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
N4 C13 C14 119.8(7) . . ?
N4 C13 C12 117.7(6) . . ?
C14 C13 C12 122.4(6) . . ?
C15 C14 C13 119.6(8) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.9(8) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C17 117.5(8) . . ?
C15 C16 H16 121.2 . . ?
C17 C16 H16 121.2 . . ?
N4 C17 C16 122.9(8) . . ?
N4 C17 H17 118.5 . . ?
C16 C17 H17 118.5 . . ?
N1 C18 C19 112.7(4) . . ?
N1 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
N1 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
O2 C19 O1 125.4(5) . . ?
O2 C19 C18 117.0(5) . . ?
O1 C19 C18 117.6(4) . . ?
C102 C101 H10A 109.5 . . ?
C102 C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
C102 C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
N101 C102 C101 168.4(16) . . ?
C1 N1 C18 114.3(4) . . ?
C1 N1 C12 113.4(5) . . ?
C18 N1 C12 111.6(4) . . ?
C1 N1 Fe1 100.7(3) . . ?
C18 N1 Fe1 108.6(3) . . ?
C12 N1 Fe1 107.3(3) . . ?
C6 N2 C2 119.7(6) . . ?
C6 N2 Fe1 130.4(5) . . ?
C2 N2 Fe1 109.9(4) . . ?
C7 N3 C11 118.2(4) . . ?
C7 N3 Fe1 112.6(3) . . ?
C11 N3 Fe1 129.2(4) . . ?
C13 N4 C17 119.2(6) . . ?
C13 N4 Fe1 116.7(4) . . ?
C17 N4 Fe1 123.5(5) . . ?
C19 O1 Fe1 118.6(3) . . ?
O1 Fe1 N4 84.95(15) . . ?
O1 Fe1 N3 152.94(16) . . ?
N4 Fe1 N3 90.91(18) . . ?
O1 Fe1 N2 88.78(15) . . ?
N4 Fe1 N2 153.04(19) . . ?
N3 Fe1 N2 82.87(17) . . ?
O1 Fe1 N1 77.85(15) . . ?
N4 Fe1 N1 77.76(19) . . ?
N3 Fe1 N1 75.14(16) . . ?
N2 Fe1 N1 75.28(19) . . ?
O1 Fe1 Cl1 106.76(11) . . ?
N4 Fe1 Cl1 100.68(15) . . ?
N3 Fe1 Cl1 100.29(12) . . ?
N2 Fe1 Cl1 106.24(14) . . ?
N1 Fe1 Cl1 175.07(11) . . ?
 
_diffrn_measured_fraction_theta_max    0.991
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    1.242
_refine_diff_density_min   -0.698
_refine_diff_density_rms    0.117