data_s93
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. Craig Matthews
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C44 H36 Cl4 Mn2 N16 O16'
_chemical_formula_weight          1296.57
 
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'
 'Mn'  'Mn'   0.3368   0.7283
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    Pbcn
_symmetry_space_group_name_hall   '-P 2n 2ab'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y+1/2, z+1/2'
 '-x, y, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y-1/2, -z-1/2'
 'x, -y, z-1/2'
 '-x-1/2, y-1/2, z'
 
_cell_length_a                    17.335(3)
_cell_length_b                    12.828(2)
_cell_length_c                    23.107(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      5138.4(15)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     6325
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Slab
_exptl_crystal_colour             Orange
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.16
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.676
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              2632
_exptl_absorpt_coefficient_mu     0.787
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8584
_exptl_absorpt_correction_T_max   0.9543
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
_exptl_special_details
;
 PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
 the entire data set is used to refine the cell, which is indexed from all
 observed reflections in a 10 degree phi range.
;
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             37974
_diffrn_reflns_av_R_equivalents   0.1823
_diffrn_reflns_av_sigmaI/netI     0.0859
_diffrn_reflns_limit_h_min        -19
_diffrn_reflns_limit_h_max        22
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -27
_diffrn_reflns_limit_l_max        29
_diffrn_reflns_theta_min          2.94
_diffrn_reflns_theta_max          27.33
_reflns_number_total              5772
_reflns_number_gt                 4484
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection
' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement        
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction         
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_computing_publication_material   ? 
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0514P)²+5.8559P] where P=(Fo²+2Fc²)/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          5772
_refine_ls_number_parameters      370
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0745
_refine_ls_R_factor_gt            0.0548
_refine_ls_wR_factor_ref          0.1422
_refine_ls_wR_factor_gt           0.1298
_refine_ls_goodness_of_fit_ref    1.066
_refine_ls_restrained_S_all       1.066
_refine_ls_shift/su_max           0.001
_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
C1 C 0.10688(16) 0.7000(2) 0.45539(14) 0.0266(6) Uani 1 1 d . . .
H1 H 0.1135 0.7731 0.4511 0.032 Uiso 1 1 calc R . .
C2 C 0.14409(16) 0.6505(2) 0.50059(14) 0.0283(7) Uani 1 1 d . . .
H2 H 0.1745 0.6889 0.5273 0.034 Uiso 1 1 calc R . .
C3 C 0.13591(16) 0.5429(2) 0.50607(14) 0.0282(7) Uani 1 1 d . . .
H3 H 0.1622 0.5063 0.5359 0.034 Uiso 1 1 calc R . .
C4 C 0.08897(15) 0.4901(2) 0.46758(14) 0.0253(6) Uani 1 1 d . . .
H4 H 0.0821 0.4169 0.4710 0.030 Uiso 1 1 calc R . .
C5 C 0.05173(14) 0.5453(2) 0.42365(12) 0.0188(6) Uani 1 1 d . . .
C6 C -0.00193(15) 0.4951(2) 0.38147(13) 0.0196(6) Uani 1 1 d . . .
C7 C -0.01886(15) 0.3885(2) 0.38029(13) 0.0230(6) Uani 1 1 d . . .
H7 H 0.0045 0.3425 0.4073 0.028 Uiso 1 1 calc R . .
C8 C -0.07012(16) 0.3509(2) 0.33931(14) 0.0247(6) Uani 1 1 d . . .
H8 H -0.0821 0.2787 0.3380 0.030 Uiso 1 1 calc R . .
C9 C -0.10387(16) 0.4193(2) 0.30021(13) 0.0238(6) Uani 1 1 d . . .
H9 H -0.1397 0.3950 0.2722 0.029 Uiso 1 1 calc R . .
C10 C -0.08394(14) 0.5244(2) 0.30311(13) 0.0198(6) Uani 1 1 d . . .
C11 C -0.10979(14) 0.6059(2) 0.26124(13) 0.0188(6) Uani 1 1 d . . .
C12 C 0.10457(15) 0.8637(2) 0.26459(13) 0.0192(6) Uani 1 1 d . . .
C13 C 0.07947(14) 0.9418(2) 0.30919(12) 0.0189(6) Uani 1 1 d . . .
C14 C 0.10091(16) 1.0460(2) 0.30958(14) 0.0246(6) Uani 1 1 d . . .
H14 H 0.1379 1.0721 0.2829 0.029 Uiso 1 1 calc R . .
C15 C 0.06659(17) 1.1109(2) 0.35025(14) 0.0286(7) Uani 1 1 d . . .
H15 H 0.0802 1.1826 0.3517 0.034 Uiso 1 1 calc R . .
C16 C 0.01282(15) 1.0717(2) 0.38856(14) 0.0252(6) Uani 1 1 d . . .
H16 H -0.0120 1.1163 0.4156 0.030 Uiso 1 1 calc R . .
C17 C -0.00450(14) 0.9654(2) 0.38703(13) 0.0199(6) Uani 1 1 d . . .
C18 C -0.06033(14) 0.9129(2) 0.42655(13) 0.0196(6) Uani 1 1 d . . .
C19 C -0.09807(16) 0.9633(2) 0.47155(14) 0.0268(6) Uani 1 1 d . . .
H19 H -0.0891 1.0352 0.4785 0.032 Uiso 1 1 calc R . .
C20 C -0.14926(16) 0.9076(3) 0.50644(14) 0.0311(7) Uani 1 1 d . . .
H20 H -0.1759 0.9412 0.5372 0.037 Uiso 1 1 calc R . .
C21 C -0.16055(16) 0.8026(3) 0.49538(15) 0.0315(7) Uani 1 1 d . . .
H21 H -0.1944 0.7625 0.5189 0.038 Uiso 1 1 calc R . .
C22 C -0.12184(16) 0.7572(2) 0.44966(15) 0.0270(7) Uani 1 1 d . . .
H22 H -0.1305 0.6854 0.4420 0.032 Uiso 1 1 calc R . .
N1 N 0.06149(12) 0.64941(18) 0.41706(11) 0.0216(5) Uani 1 1 d . . .
N2 N -0.03373(12) 0.56043(18) 0.34316(10) 0.0191(5) Uani 1 1 d . . .
N3 N -0.15066(13) 0.57928(18) 0.21446(11) 0.0234(5) Uani 1 1 d . . .
H3A H -0.1625 0.6267 0.1884 0.028 Uiso 1 1 calc R . .
H3B H -0.1657 0.5143 0.2097 0.028 Uiso 1 1 calc R . .
N4 N -0.08491(12) 0.70004(17) 0.27217(11) 0.0186(5) Uani 1 1 d . . .
N5 N 0.08523(12) 0.76702(17) 0.27646(11) 0.0188(5) Uani 1 1 d . . .
N6 N 0.13872(12) 0.89488(18) 0.21584(11) 0.0210(5) Uani 1 1 d . . .
H6A H 0.1499 0.8492 0.1887 0.025 Uiso 1 1 calc R . .
H6B H 0.1500 0.9611 0.2108 0.025 Uiso 1 1 calc R . .
N7 N 0.02878(12) 0.90238(17) 0.34794(10) 0.0188(5) Uani 1 1 d . . .
N8 N -0.07232(12) 0.80967(18) 0.41539(11) 0.0215(5) Uani 1 1 d . . .
Mn1 Mn -0.00254(2) 0.73176(3) 0.34464(2) 0.01907(14) Uani 1 1 d . . .
O1 O -0.24819(14) 0.7462(2) 0.34947(14) 0.0488(7) Uani 1 1 d . . .
O2 O -0.32459(17) 0.6575(2) 0.41481(13) 0.0584(8) Uani 1 1 d . . .
O3 O -0.33332(19) 0.6155(2) 0.31817(14) 0.0684(10) Uani 1 1 d . . .
O4 O -0.22294(14) 0.5690(2) 0.37071(13) 0.0544(8) Uani 1 1 d . . .
Cl1 Cl -0.28109(4) 0.64661(5) 0.36302(3) 0.02577(18) Uani 1 1 d . . .
O11 O -0.24130(12) 0.38407(19) 0.19056(11) 0.0393(6) Uani 1 1 d . . .
O12 O -0.27345(14) 0.3849(2) 0.09174(12) 0.0477(7) Uani 1 1 d . . .
O13 O -0.25367(13) 0.22486(17) 0.13951(11) 0.0361(6) Uani 1 1 d . . .
O14 O -0.14889(12) 0.33680(18) 0.12166(12) 0.0385(6) Uani 1 1 d . . .
Cl11 Cl -0.22964(4) 0.33285(5) 0.13574(3) 0.02332(17) Uani 1 1 d . . .
 
 
_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 1.351(4) . ?
C1 C2 1.382(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.393(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(4) . ?
C4 H4 0.9500 . ?
C5 N1 1.355(4) . ?
C5 C6 1.493(4) . ?
C6 N2 1.338(4) . ?
C6 C7 1.398(4) . ?
C7 C8 1.386(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(4) . ?
C9 H9 0.9500 . ?
C10 N2 1.352(4) . ?
C10 C11 1.494(4) . ?
C11 N4 1.306(3) . ?
C11 N3 1.337(4) . ?
C12 N5 1.314(3) . ?
C12 N6 1.334(4) . ?
C12 C13 1.501(4) . ?
C13 N7 1.352(3) . ?
C13 C14 1.388(4) . ?
C14 C15 1.390(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.396(4) . ?
C16 H16 0.9500 . ?
C17 N7 1.343(4) . ?
C17 C18 1.491(4) . ?
C18 N8 1.365(4) . ?
C18 C19 1.388(4) . ?
C19 C20 1.395(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.380(5) . ?
C21 H21 0.9500 . ?
C22 N8 1.348(4) . ?
C22 H22 0.9500 . ?
N1 Mn1 2.269(2) . ?
N2 Mn1 2.264(2) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 N5 1.415(3) 3 ?
N4 Mn1 2.238(2) . ?
N5 N4 1.415(3) 3 ?
N5 Mn1 2.236(2) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N7 Mn1 2.256(2) . ?
N8 Mn1 2.266(2) . ?
O1 Cl1 1.434(3) . ?
O2 Cl1 1.421(3) . ?
O3 Cl1 1.433(3) . ?
O4 Cl1 1.428(2) . ?
O11 Cl11 1.441(2) . ?
O12 Cl11 1.434(2) . ?
O13 Cl11 1.449(2) . ?
O14 Cl11 1.438(2) . ?
 
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 123.1(3) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 118.4(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 119.1(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.6(3) . . ?
N1 C5 C6 115.4(2) . . ?
C4 C5 C6 123.0(3) . . ?
N2 C6 C7 120.9(3) . . ?
N2 C6 C5 114.7(2) . . ?
C7 C6 C5 124.4(3) . . ?
C8 C7 C6 119.3(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 119.6(3) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 118.4(3) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
N2 C10 C9 121.6(3) . . ?
N2 C10 C11 113.4(2) . . ?
C9 C10 C11 124.9(3) . . ?
N4 C11 N3 124.6(3) . . ?
N4 C11 C10 115.0(2) . . ?
N3 C11 C10 120.2(2) . . ?
N5 C12 N6 124.9(3) . . ?
N5 C12 C13 114.4(2) . . ?
N6 C12 C13 120.6(2) . . ?
N7 C13 C14 122.0(3) . . ?
N7 C13 C12 113.2(2) . . ?
C14 C13 C12 124.7(3) . . ?
C13 C14 C15 117.9(3) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.0(3) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
N7 C17 C16 120.8(3) . . ?
N7 C17 C18 114.7(2) . . ?
C16 C17 C18 124.4(3) . . ?
N8 C18 C19 121.4(3) . . ?
N8 C18 C17 114.9(2) . . ?
C19 C18 C17 123.6(3) . . ?
C18 C19 C20 119.6(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 118.7(3) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C22 C21 C20 118.9(3) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
N8 C22 C21 123.2(3) . . ?
N8 C22 H22 118.4 . . ?
C21 C22 H22 118.4 . . ?
C1 N1 C5 118.2(3) . . ?
C1 N1 Mn1 123.02(19) . . ?
C5 N1 Mn1 118.74(19) . . ?
C6 N2 C10 120.3(2) . . ?
C6 N2 Mn1 119.99(19) . . ?
C10 N2 Mn1 119.75(18) . . ?
C11 N3 H3A 120.0 . . ?
C11 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C11 N4 N5 114.0(2) . 3 ?
C11 N4 Mn1 121.55(18) . . ?
N5 N4 Mn1 119.11(15) 3 . ?
C12 N5 N4 114.1(2) . 3 ?
C12 N5 Mn1 120.77(18) . . ?
N4 N5 Mn1 115.73(15) 3 . ?
C12 N6 H6A 120.0 . . ?
C12 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C17 N7 C13 120.0(2) . . ?
C17 N7 Mn1 120.24(18) . . ?
C13 N7 Mn1 119.75(18) . . ?
C22 N8 C18 118.1(3) . . ?
C22 N8 Mn1 122.9(2) . . ?
C18 N8 Mn1 118.88(18) . . ?
N5 Mn1 N4 86.78(9) . . ?
N5 Mn1 N7 70.36(8) . . ?
N4 Mn1 N7 110.81(8) . . ?
N5 Mn1 N2 110.37(8) . . ?
N4 Mn1 N2 70.11(8) . . ?
N7 Mn1 N2 178.92(9) . . ?
N5 Mn1 N8 141.46(8) . . ?
N4 Mn1 N8 106.23(8) . . ?
N7 Mn1 N8 71.11(8) . . ?
N2 Mn1 N8 108.16(8) . . ?
N5 Mn1 N1 106.31(8) . . ?
N4 Mn1 N1 141.19(8) . . ?
N7 Mn1 N1 108.00(8) . . ?
N2 Mn1 N1 71.09(8) . . ?
N8 Mn1 N1 86.24(9) . . ?
O2 Cl1 O4 109.78(18) . . ?
O2 Cl1 O3 107.5(2) . . ?
O4 Cl1 O3 109.99(17) . . ?
O2 Cl1 O1 107.89(17) . . ?
O4 Cl1 O1 111.57(17) . . ?
O3 Cl1 O1 109.97(18) . . ?
O12 Cl11 O14 109.81(16) . . ?
O12 Cl11 O11 109.68(16) . . ?
O14 Cl11 O11 108.61(14) . . ?
O12 Cl11 O13 109.59(15) . . ?
O14 Cl11 O13 109.09(14) . . ?
O11 Cl11 O13 110.04(15) . . ?
 
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
N3 H3A O13  0.88 2.23 3.039(3) 152.8 8_565
N3 H3B O11  0.88 2.17 3.007(3) 159.0 .
N6 H6A O1  0.88 2.33 3.084(3) 144.0 3
N6 H6B O3  0.88 2.11 2.977(4) 168.2 6_666
 
_diffrn_measured_fraction_theta_max    0.996
_diffrn_reflns_theta_full              27.33
_diffrn_measured_fraction_theta_full   0.996
_refine_diff_density_max    0.675
_refine_diff_density_min   -0.555
_refine_diff_density_rms    0.109
