data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr. Craig Matthews
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C24 H24 Cl2 Cu2 N10 O12'
_chemical_formula_weight          842.51
 
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'
 'Cu'  'Cu'   0.3201   1.2651
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Triclinic
_symmetry_space_group_name_H-M    P-1
_symmetry_space_group_name_hall   '-P 1'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    9.3024(5)
_cell_length_b                    9.7983(6)
_cell_length_c                    10.0972(6)
_cell_angle_alpha                 110.719(2)
_cell_angle_beta                  109.620(2)
_cell_angle_gamma                 102.964(2)
_cell_volume                      746.81(8)
_cell_formula_units_Z             1
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3108
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Blue
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.12
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.873
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              426
_exptl_absorpt_coefficient_mu     1.686
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7291
_exptl_absorpt_correction_T_max   0.8233
_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             12263
_diffrn_reflns_av_R_equivalents   0.0549
_diffrn_reflns_av_sigmaI/netI     0.0629
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.64
_diffrn_reflns_theta_max          27.43
_reflns_number_total              3346
_reflns_number_gt                 2394
_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)+(0.0627P)²+1.6883P] where P=(Fo²+2Fc²)/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      SHELXL
_refine_ls_extinction_coef        0.030(4)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3346
_refine_ls_number_parameters      239
_refine_ls_number_restraints      6
_refine_ls_R_factor_all           0.0841
_refine_ls_R_factor_gt            0.0532
_refine_ls_wR_factor_ref          0.1470
_refine_ls_wR_factor_gt           0.1325
_refine_ls_goodness_of_fit_ref    1.036
_refine_ls_restrained_S_all       1.035
_refine_ls_shift/su_max           0.000
_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 0.3095(6) 0.5736(6) 0.2998(5) 0.0328(10) Uani 1 1 d . . .
H1 H 0.4202 0.5801 0.3405 0.039 Uiso 1 1 calc R . .
C2 C 0.2830(6) 0.7120(6) 0.3408(5) 0.0340(10) Uani 1 1 d . . .
H2 H 0.3740 0.8116 0.4063 0.041 Uiso 1 1 calc R . .
C3 C 0.1228(6) 0.7044(6) 0.2858(5) 0.0344(10) Uani 1 1 d . . .
H3 H 0.1018 0.7985 0.3141 0.041 Uiso 1 1 calc R . .
C4 C -0.0067(5) 0.5581(5) 0.1889(5) 0.0324(10) Uani 1 1 d . . .
H4 H -0.1181 0.5501 0.1497 0.039 Uiso 1 1 calc R . .
C5 C 0.0278(5) 0.4238(5) 0.1501(5) 0.0303(9) Uani 1 1 d . . .
C6 C -0.0970(5) 0.2630(5) 0.0510(6) 0.0314(10) Uani 1 1 d . . .
C7 C -0.3029(5) 0.0484(5) -0.0884(5) 0.0301(10) Uani 1 1 d . . .
C8 C -0.4613(5) -0.0860(5) -0.1807(5) 0.0302(9) Uani 1 1 d . . .
C9 C -0.6141(5) -0.0756(6) -0.2335(5) 0.0351(10) Uani 1 1 d . . .
H9 H -0.6214 0.0244 -0.2126 0.042 Uiso 1 1 calc R . .
C10 C -0.7567(6) -0.2126(7) -0.3172(6) 0.0418(12) Uani 1 1 d . . .
H10 H -0.8627 -0.2079 -0.3560 0.050 Uiso 1 1 calc R . .
C11 C -0.7424(6) -0.3558(6) -0.3434(5) 0.0366(11) Uani 1 1 d . . .
H11 H -0.8380 -0.4514 -0.3998 0.044 Uiso 1 1 calc R . .
C12 C -0.5854(5) -0.3566(6) -0.2856(5) 0.0334(10) Uani 1 1 d . . .
H12 H -0.5758 -0.4551 -0.3015 0.040 Uiso 1 1 calc R . .
N1 N 0.1866(4) 0.4303(4) 0.2055(4) 0.0297(8) Uani 1 1 d . . .
N2 N -0.0383(5) 0.1493(5) 0.0359(6) 0.0394(10) Uani 1 1 d . . .
N3 N -0.1705(4) 0.0109(5) -0.0537(5) 0.0366(9) Uani 1 1 d . . .
N4 N -0.2632(4) 0.2060(4) -0.0245(4) 0.0296(8) Uani 1 1 d . . .
N5 N -0.4474(4) -0.2275(4) -0.2091(4) 0.0298(8) Uani 1 1 d . . .
O1 O 0.2125(4) 0.2285(4) -0.0874(4) 0.0361(7) Uani 1 1 d D . .
Cu1 Cu 0.20073(6) 0.20925(7) 0.12291(8) 0.0381(3) Uani 1 1 d . . .
H1A H 0.309(2) 0.253(6) -0.078(6) 0.057 Uiso 1 1 d D . .
H1B H 0.149(4) 0.156(5) -0.180(3) 0.057 Uiso 1 1 d D . .
O21 O -0.1649(5) -0.2643(5) -0.5943(5) 0.0597(11) Uani 1 1 d . . .
O22 O -0.2805(5) -0.2757(4) -0.4256(4) 0.0508(9) Uani 1 1 d . . .
O23 O -0.3042(5) -0.0999(5) -0.5303(5) 0.0623(11) Uani 1 1 d . . .
O24 O -0.0474(4) -0.0533(4) -0.3375(4) 0.0518(10) Uani 1 1 d . . .
Cl21 Cl -0.19916(12) -0.17256(13) -0.47204(12) 0.0307(3) Uani 1 1 d . . .
O1W O -0.5023(5) -0.3525(7) -0.9096(6) 0.0700(14) Uani 1 1 d D . .
H1WA H -0.575(7) -0.321(8) -0.947(7) 0.105 Uiso 1 1 d D . .
H1WB H -0.457(9) -0.299(8) -0.8104(15) 0.105 Uiso 1 1 d 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 1.337(6) . ?
C1 C2 1.376(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.378(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(6) . ?
C4 H4 0.9500 . ?
C5 N1 1.369(5) . ?
C5 C6 1.455(7) . ?
C6 N2 1.330(5) . ?
C6 N4 1.343(5) . ?
C7 N3 1.334(5) . ?
C7 N4 1.347(6) . ?
C7 C8 1.454(6) . ?
C8 N5 1.358(6) . ?
C8 C9 1.382(6) . ?
C9 C10 1.385(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(6) . ?
C11 H11 0.9500 . ?
C12 N5 1.327(6) . ?
C12 H12 0.9500 . ?
N1 Cu1 2.081(4) . ?
N2 N3 1.344(6) . ?
N2 Cu1 1.949(4) . ?
N3 Cu1 1.936(4) 2 ?
N5 Cu1 2.102(3) 2 ?
O1 Cu1 2.233(3) . ?
O1 H1A 0.837(10) . ?
O1 H1B 0.837(10) . ?
Cu1 N3 1.936(4) 2 ?
Cu1 N5 2.102(3) 2 ?
O21 Cl21 1.429(4) . ?
O22 Cl21 1.430(4) . ?
O23 Cl21 1.425(4) . ?
O24 Cl21 1.433(3) . ?
O1W H1WA 0.840(10) . ?
O1W H1WB 0.838(10) . ?
 
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(4) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 119.1(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 119.1(4) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 119.0(4) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 122.2(4) . . ?
N1 C5 C6 113.3(4) . . ?
C4 C5 C6 124.5(4) . . ?
N2 C6 N4 112.8(4) . . ?
N2 C6 C5 115.1(4) . . ?
N4 C6 C5 132.0(4) . . ?
N3 C7 N4 112.9(4) . . ?
N3 C7 C8 114.8(4) . . ?
N4 C7 C8 132.2(4) . . ?
N5 C8 C9 121.5(4) . . ?
N5 C8 C7 113.6(3) . . ?
C9 C8 C7 124.8(4) . . ?
C8 C9 C10 119.3(4) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 119.0(4) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 118.3(5) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
N5 C12 C11 123.5(4) . . ?
N5 C12 H12 118.2 . . ?
C11 C12 H12 118.2 . . ?
C1 N1 C5 117.4(4) . . ?
C1 N1 Cu1 129.0(3) . . ?
C5 N1 Cu1 113.6(3) . . ?
C6 N2 N3 106.6(3) . . ?
C6 N2 Cu1 118.6(3) . . ?
N3 N2 Cu1 134.6(3) . . ?
C7 N3 N2 105.8(4) . . ?
C7 N3 Cu1 119.5(3) . 2 ?
N2 N3 Cu1 134.5(3) . 2 ?
C6 N4 C7 101.8(3) . . ?
C12 N5 C8 118.2(4) . . ?
C12 N5 Cu1 128.4(3) . 2 ?
C8 N5 Cu1 113.4(3) . 2 ?
Cu1 O1 H1A 113(4) . . ?
Cu1 O1 H1B 121(4) . . ?
H1A O1 H1B 107.5(17) . . ?
N3 Cu1 N2 90.41(15) 2 . ?
N3 Cu1 N1 167.00(14) 2 . ?
N2 Cu1 N1 78.88(15) . . ?
N3 Cu1 N5 78.51(15) 2 2 ?
N2 Cu1 N5 168.68(15) . 2 ?
N1 Cu1 N5 111.78(14) . 2 ?
N3 Cu1 O1 98.47(15) 2 . ?
N2 Cu1 O1 94.14(15) . . ?
N1 Cu1 O1 89.71(13) . . ?
N5 Cu1 O1 89.82(13) 2 . ?
O23 Cl21 O21 109.8(3) . . ?
O23 Cl21 O22 109.5(3) . . ?
O21 Cl21 O22 108.5(2) . . ?
O23 Cl21 O24 109.8(2) . . ?
O21 Cl21 O24 109.8(2) . . ?
O22 Cl21 O24 109.3(2) . . ?
H1WA O1W H1WB 107.3(18) . . ?
 
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
O1 H1A O1W  0.837(10) 1.91(2) 2.712(5) 160(6) 2_554
O1 H1B O24  0.837(10) 2.03(3) 2.796(4) 152(5) .
O1W H1WA N4  0.840(10) 2.08(2) 2.894(5) 165(6) 2_454
O1W H1WB O23  0.838(10) 2.45(2) 3.271(7) 168(8) .
 
_diffrn_measured_fraction_theta_max    0.981
_diffrn_reflns_theta_full              27.43
_diffrn_measured_fraction_theta_full   0.981
_refine_diff_density_max    0.779
_refine_diff_density_min   -0.899
_refine_diff_density_rms    0.104
