data_bertozzi04
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 bertozzi04
;
_chemical_name_common             EMS-VIII-007C
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C24 H20 F4 O2'
_chemical_formula_weight          416.40
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 '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'
 'O'  'O'   0.0492   0.0322
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F'  'F'   0.0727   0.0534
 '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
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.5863(4)
_cell_length_b                    8.9598(5)
_cell_length_c                    14.6268(8)
_cell_angle_alpha                 91.070(3)
_cell_angle_beta                  96.218(2)
_cell_angle_gamma                 104.754(3)
_cell_volume                      954.66(9)
_cell_formula_units_Z             2
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     9896
_cell_measurement_theta_min       5.11
_cell_measurement_theta_max       67.85
 
_exptl_crystal_description        prism
_exptl_crystal_colour             colorless
_exptl_crystal_size_max           0.12
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.449
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              432
_exptl_absorpt_coefficient_mu     0.999
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8895
_exptl_absorpt_correction_T_max   0.9517
_exptl_absorpt_process_details    SADABS

_diffrn_refln_scan_width					1.0
_diffrn_refln_scan_rate						5
_space_group.centring_type			  primitive
_space_group.IT_number						2
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_radiation_source          'microfocus rotating anode'
_diffrn_radiation_monochromator   'HELIOS multilayer mirrors'
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'phi and omega scans'
_diffrn_detector_area_resol_mean  8.366
_diffrn_reflns_number             16000
_diffrn_reflns_av_R_equivalents   0.0180
_diffrn_reflns_av_sigmaI/netI     0.0141
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          3.04
_diffrn_reflns_theta_max          68.25
_reflns_number_total              3374
_reflns_number_gt                 3104
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'Bruker APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SIR-2008'
_computing_structure_refinement   'SHELXL-97'
_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^)+(0.0470P)^2^+0.3902P] 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          3374
_refine_ls_number_parameters      271
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0351
_refine_ls_R_factor_gt            0.0322
_refine_ls_wR_factor_ref          0.0883
_refine_ls_wR_factor_gt           0.0853
_refine_ls_goodness_of_fit_ref    1.036
_refine_ls_restrained_S_all       1.036
_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 1.22517(16) 0.29612(14) 0.68962(8) 0.0177(3) Uani 1 1 d . . .
C2 C 1.25157(17) 0.19321(14) 0.76880(8) 0.0186(3) Uani 1 1 d . . .
C3 C 1.40680(17) 0.11813(13) 0.77786(8) 0.0184(3) Uani 1 1 d . . .
C4 C 1.40734(18) 0.01935(14) 0.85111(9) 0.0221(3) Uani 1 1 d . . .
H4 H 1.3087 0.0003 0.8878 0.026 Uiso 1 1 calc R . .
C5 C 1.54864(19) -0.05075(15) 0.87084(10) 0.0259(3) Uani 1 1 d . . .
H5 H 1.5478 -0.1165 0.9211 0.031 Uiso 1 1 calc R . .
C6 C 1.69156(19) -0.02441(16) 0.81675(10) 0.0282(3) Uani 1 1 d . . .
H6 H 1.7895 -0.0719 0.8299 0.034 Uiso 1 1 calc R . .
C7 C 1.69123(19) 0.07126(16) 0.74357(10) 0.0261(3) Uani 1 1 d . . .
H7 H 1.7895 0.0874 0.7067 0.031 Uiso 1 1 calc R . .
C8 C 1.55152(17) 0.14486(14) 0.72207(9) 0.0201(3) Uani 1 1 d . . .
C9 C 1.56778(17) 0.24327(15) 0.63869(9) 0.0213(3) Uani 1 1 d . . .
H9A H 1.6972 0.2714 0.6258 0.026 Uiso 1 1 calc R . .
H9B H 1.5341 0.3401 0.6531 0.026 Uiso 1 1 calc R . .
C10 C 1.44480(19) 0.16164(15) 0.55153(9) 0.0227(3) Uani 1 1 d . . .
H10A H 1.5199 0.1735 0.4995 0.027 Uiso 1 1 calc R . .
H10B H 1.4037 0.0498 0.5618 0.027 Uiso 1 1 calc R . .
C11 C 1.27605(18) 0.22075(15) 0.52382(9) 0.0211(3) Uani 1 1 d . . .
H11A H 1.3165 0.3305 0.5087 0.025 Uiso 1 1 calc R . .
H11B H 1.2069 0.1617 0.4676 0.025 Uiso 1 1 calc R . .
C12 C 1.15019(17) 0.20716(14) 0.59766(9) 0.0207(3) Uani 1 1 d . . .
C13 C 1.25584(16) 0.44740(14) 0.70964(8) 0.0179(3) Uani 1 1 d . . .
C14 C 1.33255(17) 0.50577(13) 0.80836(8) 0.0179(3) Uani 1 1 d . . .
C15 C 1.22647(17) 0.57222(13) 0.87110(8) 0.0177(3) Uani 1 1 d . . .
C16 C 1.31743(18) 0.61939(14) 0.95970(9) 0.0201(3) Uani 1 1 d . . .
H16 H 1.4365 0.6049 0.9757 0.024 Uiso 1 1 calc R . .
C17 C 1.23713(19) 0.68646(14) 1.02399(9) 0.0234(3) Uani 1 1 d . . .
H17 H 1.2997 0.7163 1.0840 0.028 Uiso 1 1 calc R . .
C18 C 1.06459(19) 0.70997(15) 1.00048(9) 0.0246(3) Uani 1 1 d . . .
H18 H 1.0102 0.7596 1.0435 0.029 Uiso 1 1 calc R . .
C19 C 0.97202(18) 0.66092(14) 0.91419(9) 0.0221(3) Uani 1 1 d . . .
H19 H 0.8531 0.6762 0.8992 0.027 Uiso 1 1 calc R . .
C20 C 1.04794(17) 0.58940(14) 0.84824(9) 0.0192(3) Uani 1 1 d . . .
C21 C 0.93250(18) 0.53673(16) 0.75735(9) 0.0245(3) Uani 1 1 d . . .
H21A H 0.8014 0.5194 0.7662 0.029 Uiso 1 1 calc R . .
H21B H 0.9516 0.4368 0.7366 0.029 Uiso 1 1 calc R . .
C22 C 0.9776(2) 0.65343(18) 0.68193(10) 0.0303(3) Uani 1 1 d . . .
H22A H 0.9085 0.6061 0.6227 0.036 Uiso 1 1 calc R . .
H22B H 0.9343 0.7453 0.6969 0.036 Uiso 1 1 calc R . .
C23 C 1.1806(2) 0.70613(15) 0.66971(9) 0.0248(3) Uani 1 1 d . . .
H23A H 1.1971 0.7831 0.6216 0.030 Uiso 1 1 calc R . .
H23B H 1.2494 0.7578 0.7280 0.030 Uiso 1 1 calc R . .
C24 C 1.26019(18) 0.57652(15) 0.64328(9) 0.0222(3) Uani 1 1 d . . .
O1 O 1.14262(13) 0.17729(11) 0.82515(7) 0.0276(2) Uani 1 1 d . . .
O2 O 1.48697(12) 0.49489(11) 0.83327(7) 0.0268(2) Uani 1 1 d . . .
F1 F 0.98982(10) 0.24114(10) 0.56413(5) 0.0290(2) Uani 1 1 d . . .
F2 F 1.09469(11) 0.05262(8) 0.61816(5) 0.02641(19) Uani 1 1 d . . .
F3 F 1.18425(14) 0.52076(9) 0.55674(5) 0.0344(2) Uani 1 1 d . . .
F4 F 1.44464(12) 0.63702(11) 0.63503(7) 0.0399(2) Uani 1 1 d . . .
 
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 0.0153(6) 0.0228(6) 0.0163(6) 0.0003(5) 0.0042(5) 0.0066(5)
C2 0.0198(6) 0.0175(6) 0.0171(6) -0.0015(5) 0.0029(5) 0.0021(5)
C3 0.0198(6) 0.0156(6) 0.0180(6) -0.0005(5) 0.0008(5) 0.0019(5)
C4 0.0231(6) 0.0196(6) 0.0203(6) 0.0005(5) 0.0017(5) 0.0000(5)
C5 0.0311(7) 0.0192(6) 0.0245(7) 0.0054(5) -0.0032(6) 0.0037(5)
C6 0.0274(7) 0.0247(7) 0.0344(8) 0.0033(6) -0.0012(6) 0.0122(6)
C7 0.0245(7) 0.0271(7) 0.0290(7) 0.0027(5) 0.0057(6) 0.0096(5)
C8 0.0210(6) 0.0182(6) 0.0205(6) 0.0001(5) 0.0024(5) 0.0043(5)
C9 0.0192(6) 0.0233(6) 0.0234(7) 0.0049(5) 0.0076(5) 0.0070(5)
C10 0.0299(7) 0.0231(6) 0.0190(6) 0.0028(5) 0.0102(5) 0.0110(5)
C11 0.0268(7) 0.0219(6) 0.0151(6) -0.0015(5) 0.0028(5) 0.0073(5)
C12 0.0203(6) 0.0211(6) 0.0205(7) -0.0013(5) 0.0012(5) 0.0058(5)
C13 0.0169(6) 0.0226(6) 0.0158(6) 0.0013(5) 0.0037(5) 0.0075(5)
C14 0.0193(6) 0.0160(6) 0.0178(6) 0.0027(5) 0.0027(5) 0.0029(5)
C15 0.0216(6) 0.0152(6) 0.0158(6) 0.0018(4) 0.0043(5) 0.0029(5)
C16 0.0228(6) 0.0181(6) 0.0175(6) 0.0034(5) 0.0017(5) 0.0018(5)
C17 0.0321(7) 0.0200(6) 0.0149(6) 0.0000(5) 0.0043(5) 0.0002(5)
C18 0.0326(7) 0.0197(6) 0.0223(7) 0.0005(5) 0.0132(6) 0.0046(5)
C19 0.0235(6) 0.0198(6) 0.0247(7) 0.0035(5) 0.0080(5) 0.0062(5)
C20 0.0219(6) 0.0165(6) 0.0190(6) 0.0024(5) 0.0049(5) 0.0036(5)
C21 0.0192(6) 0.0321(7) 0.0231(7) -0.0033(5) 0.0005(5) 0.0096(5)
C22 0.0367(8) 0.0410(8) 0.0200(7) 0.0008(6) -0.0009(6) 0.0241(7)
C23 0.0391(8) 0.0204(6) 0.0167(6) 0.0026(5) 0.0020(6) 0.0116(6)
C24 0.0269(7) 0.0260(7) 0.0152(6) 0.0032(5) 0.0042(5) 0.0087(5)
O1 0.0290(5) 0.0313(5) 0.0264(5) 0.0078(4) 0.0134(4) 0.0103(4)
O2 0.0209(5) 0.0357(5) 0.0246(5) -0.0050(4) -0.0002(4) 0.0103(4)
F1 0.0217(4) 0.0444(5) 0.0218(4) -0.0039(3) -0.0022(3) 0.0125(3)
F2 0.0302(4) 0.0214(4) 0.0233(4) -0.0025(3) 0.0050(3) -0.0018(3)
F3 0.0647(6) 0.0320(4) 0.0135(4) 0.0005(3) 0.0013(4) 0.0264(4)
F4 0.0318(5) 0.0453(5) 0.0480(6) 0.0269(4) 0.0180(4) 0.0126(4)
 
_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 C13 1.3367(18) . ?
C1 C2 1.5217(17) . ?
C1 C12 1.5269(17) . ?
C2 O1 1.2144(15) . ?
C2 C3 1.4933(17) . ?
C3 C4 1.4027(18) . ?
C3 C8 1.4128(18) . ?
C4 C5 1.3819(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3960(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.5157(17) . ?
C9 C10 1.5462(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5247(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5040(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 F1 1.3705(15) . ?
C12 F2 1.3894(15) . ?
C13 C24 1.5202(17) . ?
C13 C14 1.5271(17) . ?
C14 O2 1.2172(16) . ?
C14 C15 1.4925(17) . ?
C15 C16 1.4041(18) . ?
C15 C20 1.4071(18) . ?
C16 C17 1.3806(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.3992(18) . ?
C19 H19 0.9500 . ?
C20 C21 1.5070(18) . ?
C21 C22 1.539(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.523(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5014(18) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 F3 1.3621(15) . ?
C24 F4 1.3853(16) . ?
 
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
C13 C1 C2 117.47(11) . . ?
C13 C1 C12 128.58(12) . . ?
C2 C1 C12 113.73(10) . . ?
O1 C2 C3 121.58(11) . . ?
O1 C2 C1 116.93(11) . . ?
C3 C2 C1 121.48(10) . . ?
C4 C3 C8 119.64(12) . . ?
C4 C3 C2 115.06(11) . . ?
C8 C3 C2 125.24(11) . . ?
C5 C4 C3 121.22(12) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.47(12) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 119.80(12) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 122.28(13) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
C7 C8 C3 117.59(12) . . ?
C7 C8 C9 116.26(11) . . ?
C3 C8 C9 126.13(11) . . ?
C8 C9 C10 113.26(10) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 115.11(10) . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C10 113.26(11) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
F1 C12 F2 103.67(10) . . ?
F1 C12 C11 110.31(10) . . ?
F2 C12 C11 108.22(10) . . ?
F1 C12 C1 109.52(10) . . ?
F2 C12 C1 105.89(10) . . ?
C11 C12 C1 118.15(11) . . ?
C1 C13 C24 128.07(11) . . ?
C1 C13 C14 117.45(11) . . ?
C24 C13 C14 113.32(10) . . ?
O2 C14 C15 121.57(11) . . ?
O2 C14 C13 115.77(11) . . ?
C15 C14 C13 122.66(11) . . ?
C16 C15 C20 119.40(11) . . ?
C16 C15 C14 115.14(11) . . ?
C20 C15 C14 125.46(11) . . ?
C17 C16 C15 121.25(12) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 119.56(12) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 119.70(12) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 122.08(12) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C19 C20 C15 117.92(12) . . ?
C19 C20 C21 117.50(12) . . ?
C15 C20 C21 124.58(11) . . ?
C20 C21 C22 113.06(11) . . ?
C20 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
C20 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C23 C22 C21 114.45(11) . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22B 108.6 . . ?
C21 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C24 C23 C22 113.44(11) . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
F3 C24 F4 104.44(10) . . ?
F3 C24 C23 108.69(11) . . ?
F4 C24 C23 108.52(11) . . ?
F3 C24 C13 111.77(11) . . ?
F4 C24 C13 104.68(10) . . ?
C23 C24 C13 117.80(10) . . ?
 
_diffrn_measured_fraction_theta_max    0.965
_diffrn_reflns_theta_full              67.00
_diffrn_measured_fraction_theta_full   0.977
_refine_diff_density_max    0.272
_refine_diff_density_min   -0.204
_refine_diff_density_rms    0.039