 
data_05src0194
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C22 H8 F10 N2 Zn'
_chemical_formula_sum
 'C22 H8 F10 N2 Zn'
_chemical_formula_weight          555.67
 
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'
 'F'  'F'   0.0171   0.0103
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Zn'  'Zn'   0.2839   1.4301
 '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)/c
_symmetry_space_group_name_hall   '-P 2ybc'
 
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'
 
_cell_length_a                    8.0151(8)
_cell_length_b                    15.5644(14)
_cell_length_c                    16.6592(10)
_cell_angle_alpha                 90.00
_cell_angle_beta                  102.337(5)
_cell_angle_gamma                 90.00
_cell_volume                      2030.2(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4731
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.818
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1096
_exptl_absorpt_coefficient_mu     1.315
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7790
_exptl_absorpt_correction_T_max   0.7790
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   '10cm confocal mirrors'
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          none
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         negligible
_diffrn_reflns_number             28500
_diffrn_reflns_av_R_equivalents   0.0366
_diffrn_reflns_av_sigmaI/netI     0.0248
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        20
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          2.91
_diffrn_reflns_theta_max          27.50
_reflns_number_total              4632
_reflns_number_gt                 4296
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_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 > 2σ(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)+(0.0330P)²+1.3758P] 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      SHELXL
_refine_ls_extinction_coef        0.0055(7)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          4632
_refine_ls_number_parameters      317
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0297
_refine_ls_R_factor_gt            0.0266
_refine_ls_wR_factor_ref          0.0704
_refine_ls_wR_factor_gt           0.0681
_refine_ls_goodness_of_fit_ref    1.023
_refine_ls_restrained_S_all       1.023
_refine_ls_shift/su_max           0.002
_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 -0.05422(19) 0.96388(10) 0.26402(9) 0.0185(3) Uani 1 1 d . . .
C2 C -0.0903(2) 1.01146(11) 0.32796(10) 0.0217(3) Uani 1 1 d . . .
C3 C -0.2024(2) 1.07960(11) 0.31826(11) 0.0250(3) Uani 1 1 d . . .
C4 C -0.2842(2) 1.10332(10) 0.24023(11) 0.0252(3) Uani 1 1 d . . .
C5 C -0.2515(2) 1.05905(11) 0.17351(10) 0.0247(3) Uani 1 1 d . . .
C6 C -0.1386(2) 0.99115(11) 0.18732(10) 0.0211(3) Uani 1 1 d . . .
C7 C -0.03974(18) 0.74548(10) 0.29931(9) 0.0186(3) Uani 1 1 d . . .
C8 C -0.06099(19) 0.72196(11) 0.37624(9) 0.0209(3) Uani 1 1 d . . .
C9 C -0.1572(2) 0.65306(11) 0.39220(10) 0.0244(3) Uani 1 1 d . . .
C10 C -0.2384(2) 0.60308(11) 0.32731(11) 0.0241(3) Uani 1 1 d . . .
C11 C -0.2227(2) 0.62358(11) 0.24882(10) 0.0231(3) Uani 1 1 d . . .
C12 C -0.12497(19) 0.69326(11) 0.23688(9) 0.0201(3) Uani 1 1 d . . .
C13 C 0.3425(2) 0.88016(12) 0.44391(10) 0.0248(3) Uani 1 1 d . . .
H13 H 0.2456 0.8845 0.4680 0.030 Uiso 1 1 calc R . .
C14 C 0.5034(2) 0.88614(13) 0.49424(11) 0.0296(4) Uani 1 1 d . . .
H14 H 0.5169 0.8938 0.5518 0.036 Uiso 1 1 calc R . .
C15 C 0.6443(2) 0.88065(13) 0.45890(11) 0.0303(4) Uani 1 1 d . . .
H15 H 0.7564 0.8846 0.4919 0.036 Uiso 1 1 calc R . .
C16 C 0.6200(2) 0.86935(11) 0.37487(11) 0.0250(3) Uani 1 1 d . . .
H16 H 0.7153 0.8656 0.3496 0.030 Uiso 1 1 calc R . .
C17 C 0.45475(19) 0.86355(10) 0.32773(10) 0.0188(3) Uani 1 1 d . . .
C18 C 0.41682(19) 0.85092(9) 0.23742(10) 0.0187(3) Uani 1 1 d . . .
C19 C 0.5432(2) 0.84654(11) 0.19214(11) 0.0243(3) Uani 1 1 d . . .
H19 H 0.6601 0.8521 0.2185 0.029 Uiso 1 1 calc R . .
C20 C 0.4968(2) 0.83396(12) 0.10797(11) 0.0285(4) Uani 1 1 d . . .
H20 H 0.5816 0.8315 0.0759 0.034 Uiso 1 1 calc R . .
C21 C 0.3268(2) 0.82503(12) 0.07131(11) 0.0269(4) Uani 1 1 d . . .
H21 H 0.2925 0.8157 0.0138 0.032 Uiso 1 1 calc R . .
C22 C 0.2065(2) 0.82997(11) 0.11990(10) 0.0225(3) Uani 1 1 d . . .
H22 H 0.0890 0.8240 0.0947 0.027 Uiso 1 1 calc R . .
N1 N 0.31795(16) 0.86853(9) 0.36265(8) 0.0196(3) Uani 1 1 d . . .
N2 N 0.25024(16) 0.84290(8) 0.20117(8) 0.0184(3) Uani 1 1 d . . .
F1 F -0.01511(14) 0.98998(7) 0.40673(6) 0.0325(2) Uani 1 1 d . . .
F2 F -0.23400(16) 1.12332(8) 0.38316(7) 0.0394(3) Uani 1 1 d . . .
F3 F -0.39481(14) 1.16896(7) 0.22871(8) 0.0370(3) Uani 1 1 d . . .
F4 F -0.33149(15) 1.08240(8) 0.09756(7) 0.0390(3) Uani 1 1 d . . .
F5 F -0.11485(14) 0.94806(7) 0.11974(6) 0.0338(3) Uani 1 1 d . . .
F6 F -0.11687(13) 0.71119(7) 0.15766(6) 0.0291(2) Uani 1 1 d . . .
F7 F -0.30479(14) 0.57496(7) 0.18552(6) 0.0327(2) Uani 1 1 d . . .
F8 F -0.33383(14) 0.53575(7) 0.34012(7) 0.0347(3) Uani 1 1 d . . .
F9 F -0.17525(16) 0.63508(8) 0.46860(7) 0.0383(3) Uani 1 1 d . . .
F10 F 0.01178(13) 0.77088(7) 0.44242(6) 0.0290(2) Uani 1 1 d . . .
Zn1 Zn 0.08468(2) 0.854676(11) 0.280701(10) 0.01719(8) Uani 1 1 d . . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.379(2) . ?
C1 C2 1.378(2) . ?
C1 Zn1 2.0182(16) . ?
C2 F1 1.3635(18) . ?
C2 C3 1.377(2) . ?
C3 F2 1.3467(19) . ?
C3 C4 1.376(2) . ?
C4 F3 1.3395(19) . ?
C4 C5 1.380(3) . ?
C5 F4 1.3407(19) . ?
C5 C6 1.378(2) . ?
C6 F5 1.3583(18) . ?
C7 C8 1.378(2) . ?
C7 C12 1.380(2) . ?
C7 Zn1 2.0277(16) . ?
C8 F10 1.3642(18) . ?
C8 C9 1.380(2) . ?
C9 F9 1.341(2) . ?
C9 C10 1.377(2) . ?
C10 F8 1.3411(19) . ?
C10 C11 1.377(2) . ?
C11 F7 1.3494(18) . ?
C11 C12 1.377(2) . ?
C12 F6 1.3640(18) . ?
C13 N1 1.338(2) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(2) . ?
C16 H16 0.9500 . ?
C17 N1 1.349(2) . ?
C17 C18 1.483(2) . ?
C18 N2 1.348(2) . ?
C18 C19 1.388(2) . ?
C19 C20 1.386(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.376(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(2) . ?
C21 H21 0.9500 . ?
C22 N2 1.339(2) . ?
C22 H22 0.9500 . ?
N1 Zn1 2.0773(13) . ?
N2 Zn1 2.0739(13) . ?
 
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
C6 C1 C2 114.11(14) . . ?
C6 C1 Zn1 122.26(12) . . ?
C2 C1 Zn1 123.16(12) . . ?
F1 C2 C3 116.41(14) . . ?
F1 C2 C1 119.32(14) . . ?
C3 C2 C1 124.25(15) . . ?
F2 C3 C2 121.68(16) . . ?
F2 C3 C4 119.31(16) . . ?
C2 C3 C4 119.01(15) . . ?
F3 C4 C3 120.49(16) . . ?
F3 C4 C5 119.96(16) . . ?
C3 C4 C5 119.55(15) . . ?
F4 C5 C6 122.00(15) . . ?
F4 C5 C4 119.35(15) . . ?
C6 C5 C4 118.64(15) . . ?
F5 C6 C1 119.22(14) . . ?
F5 C6 C5 116.33(14) . . ?
C1 C6 C5 124.42(15) . . ?
C8 C7 C12 113.87(14) . . ?
C8 C7 Zn1 121.83(12) . . ?
C12 C7 Zn1 123.97(12) . . ?
F10 C8 C9 115.99(14) . . ?
F10 C8 C7 119.14(14) . . ?
C9 C8 C7 124.83(15) . . ?
F9 C9 C10 119.90(15) . . ?
F9 C9 C8 121.56(15) . . ?
C10 C9 C8 118.53(15) . . ?
F8 C10 C9 120.42(15) . . ?
F8 C10 C11 120.19(15) . . ?
C9 C10 C11 119.39(15) . . ?
F7 C11 C12 121.75(15) . . ?
F7 C11 C10 118.94(15) . . ?
C12 C11 C10 119.31(15) . . ?
F6 C12 C11 116.56(14) . . ?
F6 C12 C7 119.36(14) . . ?
C11 C12 C7 124.07(15) . . ?
N1 C13 C14 122.63(16) . . ?
N1 C13 H13 118.7 . . ?
C14 C13 H13 118.7 . . ?
C15 C14 C13 118.56(16) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 119.18(15) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C17 119.41(16) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
N1 C17 C16 121.11(15) . . ?
N1 C17 C18 115.84(13) . . ?
C16 C17 C18 123.05(15) . . ?
N2 C18 C19 121.32(15) . . ?
N2 C18 C17 115.81(13) . . ?
C19 C18 C17 122.87(14) . . ?
C20 C19 C18 119.22(16) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C21 C20 C19 119.30(16) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 118.78(16) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
N2 C22 C21 122.23(15) . . ?
N2 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
C13 N1 C17 119.11(14) . . ?
C13 N1 Zn1 126.61(11) . . ?
C17 N1 Zn1 114.27(10) . . ?
C22 N2 C18 119.15(14) . . ?
C22 N2 Zn1 126.43(11) . . ?
C18 N2 Zn1 114.41(10) . . ?
C1 Zn1 C7 116.88(6) . . ?
C1 Zn1 N2 113.32(6) . . ?
C7 Zn1 N2 115.23(6) . . ?
C1 Zn1 N1 113.30(6) . . ?
C7 Zn1 N1 112.93(6) . . ?
N2 Zn1 N1 79.64(5) . . ?
 
_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    0.362
_refine_diff_density_min   -0.361
_refine_diff_density_rms    0.056
