# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011
data_global
_journal_name_full Org.Biomol.Chem.
_journal_coden_cambridge 0177
_publ_section_references
;
Jacobson, R. (1998). REQAB. Version 1.1. Molecular Structure
Corporation, The Woodlands, Texas, USA.
Molecular Structure Corporation & Rigaku (2006). CrystalClear MSC, The
Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). SHELXTL.Version 6.10 Acta Cryst. A64, 112-122.
;
loop_
_publ_author_name
J.D.Moody
S.T.Iacono
D.VanDerveer
D.W.
'.Smith Junior'
_publ_contact_author_name 'Smith, Dennis W., Jr.'
_publ_contact_author_email dwsmith@clemson.edu
data_jm1
_database_code_depnum_ccdc_archive 'CCDC 656776'
#TrackingRef '4428_web_deposit_cif_file_0_ScottIacono_1298927023.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C14 H8 Br2 F2 O2'
_chemical_formula_weight 406.02
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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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
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 4.0930(8)
_cell_length_b 5.6694(11)
_cell_length_c 28.901(6)
_cell_angle_alpha 90.00
_cell_angle_beta 91.42(3)
_cell_angle_gamma 90.00
_cell_volume 670.4(2)
_cell_formula_units_Z 2
_cell_measurement_temperature 153(2)
_cell_measurement_reflns_used 1645
_cell_measurement_theta_min 3.6618
_cell_measurement_theta_max 25.9729
_exptl_crystal_description prism
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.16
_exptl_crystal_size_min 0.11
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 2.011
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 392
_exptl_absorpt_coefficient_mu 6.066
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.3124
_exptl_absorpt_correction_T_max 0.5551
_exptl_absorpt_process_details 'Jacobson, R., (1998)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 153(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Sealed Tube'
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_radiation_detector CCD
_diffrn_measurement_device
;
Mercury CCD
;
_diffrn_detector_area_resol_mean 14.6306
_diffrn_measurement_method omega
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_measurement_details
;
scan:
Number of images: 260
Slice: -40.0000 - 90.0000
Image width: 0.5000
Exp time: 10.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 45.0000
Phi: 0.0000
XTD: 37.8844
2theta: 7.8422
scan:
Number of images: 240
Slice: -30.0000 - 90.0000
Image width: 0.5000
Exp time: 10.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 45.0000
Phi: 90.0000
XTD: 37.8844
2theta: 7.8422
;
_diffrn_measurement_device_details
;
AFC8: Eulerian 3 circle
;
_diffrn_standards_number 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_decay_% 0
_diffrn_reflns_number 3085
_diffrn_reflns_av_R_equivalents 0.0347
_diffrn_reflns_av_sigmaI/netI 0.0366
_diffrn_reflns_limit_h_min -3
_diffrn_reflns_limit_h_max 4
_diffrn_reflns_limit_k_min -5
_diffrn_reflns_limit_k_max 6
_diffrn_reflns_limit_l_min -32
_diffrn_reflns_limit_l_max 34
_diffrn_reflns_theta_min 3.66
_diffrn_reflns_theta_max 25.01
_reflns_number_total 1145
_reflns_number_gt 1049
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrystalClear (Rigaku/MSC,2006)'
_computing_cell_refinement 'CrystalClear (Rigaku/MSC,2006)'
_computing_data_reduction 'CrystalClear (Rigaku/MSC,2006)'
_computing_structure_solution 'SHELXTL 6.10 (Sheldrick,2008)'
_computing_structure_refinement 'SHELXTL 6.10 (Sheldrick,2008)'
_computing_molecular_graphics 'SHELXTL 6.10 (Sheldrick,2008)'
_computing_publication_material 'SHELXTL 6.10 (Sheldrick,2008)'
_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^)+(0.0263P)^2^+0.8403P] 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 1145
_refine_ls_number_parameters 91
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0356
_refine_ls_R_factor_gt 0.0315
_refine_ls_wR_factor_ref 0.0688
_refine_ls_wR_factor_gt 0.0663
_refine_ls_goodness_of_fit_ref 1.118
_refine_ls_restrained_S_all 1.118
_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
Br1 Br 0.40152(8) 0.14356(6) 0.209721(12) 0.02579(16) Uani 1 1 d . . .
O1 O -0.1280(6) -0.5010(4) 0.05915(9) 0.0275(6) Uani 1 1 d . . .
F1 F -0.2920(5) -0.2717(4) -0.00172(8) 0.0344(5) Uani 1 1 d . . .
C1 C 0.2381(8) -0.0548(6) 0.16164(12) 0.0209(8) Uani 1 1 d . . .
C2 C 0.2840(8) 0.0065(6) 0.11581(12) 0.0223(8) Uani 1 1 d . . .
H2 H 0.3982 0.1490 0.1084 0.027 Uiso 1 1 calc R . .
C3 C 0.1646(9) -0.1383(6) 0.08067(13) 0.0237(8) Uani 1 1 d . . .
H3 H 0.1944 -0.0978 0.0488 0.028 Uiso 1 1 calc R . .
C4 C 0.0014(8) -0.3427(6) 0.09251(12) 0.0204(8) Uani 1 1 d . . .
C5 C -0.0488(8) -0.4052(6) 0.13786(12) 0.0230(8) Uani 1 1 d . . .
H5 H -0.1651 -0.5470 0.1451 0.028 Uiso 1 1 calc R . .
C6 C 0.0729(8) -0.2585(6) 0.17297(13) 0.0229(8) Uani 1 1 d . . .
H6 H 0.0420 -0.2988 0.2048 0.027 Uiso 1 1 calc R . .
C7 C -0.0929(9) -0.4466(6) 0.01432(13) 0.0260(8) 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
Br1 0.0306(3) 0.0271(2) 0.0195(2) -0.00415(15) -0.00206(16) -0.00096(14)
O1 0.0384(15) 0.0266(13) 0.0178(14) -0.0038(11) 0.0039(11) -0.0107(11)
F1 0.0363(12) 0.0306(11) 0.0362(14) 0.0020(10) -0.0010(10) 0.0018(10)
C1 0.0227(18) 0.0188(17) 0.0214(19) -0.0030(15) 0.0007(14) 0.0042(14)
C2 0.0281(19) 0.0185(17) 0.020(2) 0.0028(15) -0.0004(15) -0.0018(14)
C3 0.030(2) 0.0244(18) 0.0173(19) 0.0017(16) 0.0037(15) -0.0017(15)
C4 0.0212(18) 0.0204(17) 0.0196(19) -0.0031(15) 0.0029(14) -0.0003(14)
C5 0.0210(18) 0.0251(19) 0.023(2) 0.0024(16) 0.0029(15) -0.0038(14)
C6 0.0269(19) 0.0251(18) 0.0168(19) 0.0023(16) 0.0020(14) 0.0037(15)
C7 0.034(2) 0.0240(18) 0.0202(19) 0.0005(16) -0.0015(15) -0.0061(15)
_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
Br1 C1 1.896(4) . ?
O1 C7 1.343(4) . ?
O1 C4 1.411(4) . ?
F1 C7 1.358(4) . ?
C1 C6 1.382(5) . ?
C1 C2 1.387(5) . ?
C2 C3 1.385(5) . ?
C2 H2 0.9600 . ?
C3 C4 1.384(5) . ?
C3 H3 0.9600 . ?
C4 C5 1.378(5) . ?
C5 C6 1.394(5) . ?
C5 H5 0.9600 . ?
C6 H6 0.9600 . ?
C7 C7 1.289(7) 3_545 ?
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
C7 O1 C4 117.8(3) . . ?
C6 C1 C2 121.0(3) . . ?
C6 C1 Br1 119.2(3) . . ?
C2 C1 Br1 119.9(3) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 118.6(3) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C5 C4 C3 122.3(3) . . ?
C5 C4 O1 115.1(3) . . ?
C3 C4 O1 122.6(3) . . ?
C4 C5 C6 118.7(3) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 119.6(3) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C7 C7 O1 126.2(5) 3_545 . ?
C7 C7 F1 118.8(4) 3_545 . ?
O1 C7 F1 114.8(3) . . ?
_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full 25.01
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max 0.727
_refine_diff_density_min -0.518
_refine_diff_density_rms 0.095
# Attachment '4429_web_deposit_cif_file_1_ScottIacono_1298927023.cif'
_publ_section_references
;
Jacobson, R. (1998). REQAB. Version 1.1. Molecular Structure
Corporation, The Woodlands, Texas, USA.
Molecular Structure Corporation & Rigaku (2006). CrystalClear MSC, The
Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). SHELXTL.Version 6.10 Acta Cryst. A64, 112-122.
;
data_jm2
_database_code_depnum_ccdc_archive 'CCDC 656777'
#TrackingRef '4430_web_deposit_cif_file_2_ScottIacono_1298927023.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C14 H9 Br2 F3 O2'
_chemical_formula_weight 426.03
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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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
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 12.711(3)
_cell_length_b 4.8861(10)
_cell_length_c 11.507(2)
_cell_angle_alpha 90.00
_cell_angle_beta 96.33(3)
_cell_angle_gamma 90.00
_cell_volume 710.3(2)
_cell_formula_units_Z 2
_cell_measurement_temperature 153(2)
_cell_measurement_reflns_used 2194
_cell_measurement_theta_min 3.5627
_cell_measurement_theta_max 26.4354
_exptl_crystal_description chip
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.67
_exptl_crystal_size_mid 0.62
_exptl_crystal_size_min 0.26
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.992
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 412
_exptl_absorpt_coefficient_mu 5.740
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.1137
_exptl_absorpt_correction_T_max 0.3168
_exptl_absorpt_process_details 'Jacobson, R., (1998)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 153(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Sealed Tube'
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_radiation_detector CCD
_diffrn_measurement_device
;
Mercury CCD
;
_diffrn_detector_area_resol_mean 14.6306
_diffrn_measurement_method omega
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_measurement_details
;
scan:
Number of images: 260
Slice: -40.0000 - 90.0000
Image width: 0.5000
Exp time: 15.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 45.0000
Phi: 0.0000
XTD: 27.6256
2theta: -0.1262
scan:
Number of images: 220
Slice: -30.0000 - 80.0000
Image width: 0.5000
Exp time: 15.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 45.0000
Phi: 90.0000
XTD: 27.6256
2theta: -0.1262
;
_diffrn_measurement_device_details
;
AFC8: Eulerian 3 circle
;
_diffrn_standards_number 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_decay_% 0
_diffrn_reflns_number 4677
_diffrn_reflns_av_R_equivalents 0.0378
_diffrn_reflns_av_sigmaI/netI 0.0282
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -5
_diffrn_reflns_limit_k_max 5
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_theta_min 3.56
_diffrn_reflns_theta_max 25.52
_reflns_number_total 1300
_reflns_number_gt 1211
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrystalClear (Rigaku/MSC,2006)'
_computing_cell_refinement 'CrystalClear (Rigaku/MSC,2006)'
_computing_data_reduction 'CrystalClear (Rigaku/MSC,2006)'
_computing_structure_solution 'SHELXTL 6.10 (Sheldrick,2008)'
_computing_structure_refinement 'SHELXTL 6.10 (Sheldrick,2008)'
_computing_molecular_graphics 'SHELXTL 6.10 (Sheldrick,2008)'
_computing_publication_material 'SHELXTL 6.10 (Sheldrick,2008)'
_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^)+(0.0457P)^2^+0.8265P] 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 1300
_refine_ls_number_parameters 100
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0346
_refine_ls_R_factor_gt 0.0325
_refine_ls_wR_factor_ref 0.0851
_refine_ls_wR_factor_gt 0.0833
_refine_ls_goodness_of_fit_ref 1.148
_refine_ls_restrained_S_all 1.148
_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
Br1 Br 0.93185(2) 0.07494(6) 0.82473(3) 0.02488(17) Uani 1 1 d . . .
F1 F 0.5312(2) 1.0837(5) 0.8592(2) 0.0366(6) Uani 0.83 1 d P . .
F2 F 0.4716(3) 0.7003(7) 0.9175(3) 0.0424(8) Uani 0.67 1 d P . .
C1 C 0.8355(2) 0.3294(7) 0.8794(3) 0.0223(6) Uani 1 1 d . . .
C2 C 0.7526(3) 0.4254(7) 0.8033(3) 0.0256(7) Uani 1 1 d . . .
H2 H 0.7438 0.3650 0.7235 0.031 Uiso 1 1 calc R . .
C3 C 0.6817(3) 0.6108(7) 0.8431(3) 0.0305(8) Uani 1 1 d . . .
H3 H 0.6238 0.6812 0.7909 0.037 Uiso 1 1 calc R . .
C4 C 0.6956(3) 0.6920(7) 0.9584(3) 0.0281(7) Uani 1 1 d . . .
C5 C 0.7794(3) 0.5956(7) 1.0350(3) 0.0294(8) Uani 1 1 d . . .
H5 H 0.7879 0.6542 1.1151 0.035 Uiso 1 1 calc R . .
C6 C 0.8500(3) 0.4153(7) 0.9948(3) 0.0254(7) Uani 1 1 d . . .
H6 H 0.9091 0.3491 1.0463 0.031 Uiso 1 1 calc R . .
C7 C 0.5299(3) 0.9219(6) 0.9573(3) 0.0252(7) Uani 1 1 d . . .
H7A H 0.4938 0.7533 0.9350 0.030 Uiso 0.32 1 d P . .
H7B H 0.5307 1.0310 0.8861 0.030 Uiso 0.18 1 d P . .
O1 O 0.6287(2) 0.8750(7) 1.0091(2) 0.0443(8) 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
Br1 0.0248(2) 0.0272(2) 0.0231(2) 0.00009(11) 0.00453(14) 0.00410(11)
F1 0.0411(15) 0.0377(15) 0.0313(14) 0.0079(10) 0.0050(11) 0.0070(11)
F2 0.0379(18) 0.0392(19) 0.050(2) -0.0160(16) 0.0053(15) -0.0044(14)
C1 0.0186(15) 0.0240(16) 0.0245(15) 0.0014(13) 0.0033(12) -0.0023(12)
C2 0.0246(17) 0.0310(18) 0.0205(17) -0.0039(12) -0.0001(13) 0.0008(12)
C3 0.0223(17) 0.0394(19) 0.0276(18) -0.0037(15) -0.0069(13) 0.0067(14)
C4 0.0227(16) 0.0338(19) 0.0275(17) -0.0056(14) 0.0013(13) 0.0052(14)
C5 0.0264(18) 0.036(2) 0.0243(18) -0.0021(14) -0.0048(14) 0.0079(14)
C6 0.0224(17) 0.0310(18) 0.0219(16) 0.0027(12) -0.0020(13) 0.0053(12)
C7 0.0195(16) 0.0268(18) 0.0280(17) -0.0010(13) -0.0034(13) 0.0012(12)
O1 0.0262(14) 0.0660(19) 0.0380(15) -0.0216(14) -0.0093(11) 0.0218(13)
_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
Br1 C1 1.900(3) . ?
F1 C7 1.381(4) . ?
F1 H7B 0.404(2) . ?
F2 C7 1.363(5) . ?
F2 H7A 0.418(3) . ?
C1 C2 1.376(5) . ?
C1 C6 1.385(5) . ?
C2 C3 1.391(5) . ?
C2 H2 0.9600 . ?
C3 C4 1.377(5) . ?
C3 H3 0.9600 . ?
C4 C5 1.388(5) . ?
C4 O1 1.404(4) . ?
C5 C6 1.374(5) . ?
C5 H5 0.9600 . ?
C6 H6 0.9600 . ?
C7 O1 1.349(4) . ?
C7 C7 1.513(7) 3_677 ?
C7 H7A 0.964(3) . ?
C7 H7B 0.979(3) . ?
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
C7 F1 H7B 4.7(3) . . ?
C7 F2 H7A 14.6(4) . . ?
C2 C1 C6 121.2(3) . . ?
C2 C1 Br1 119.3(2) . . ?
C6 C1 Br1 119.5(2) . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 O1 124.3(3) . . ?
C5 C4 O1 114.2(3) . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
O1 C7 F2 117.3(3) . . ?
O1 C7 F1 111.4(3) . . ?
F2 C7 F1 103.5(3) . . ?
O1 C7 C7 108.0(3) . 3_677 ?
F2 C7 C7 109.0(4) . 3_677 ?
F1 C7 C7 107.1(3) . 3_677 ?
O1 C7 H7A 111.5(3) . . ?
F2 C7 H7A 6.27(16) . . ?
F1 C7 H7A 108.6(3) . . ?
C7 C7 H7A 110.2(4) 3_677 . ?
O1 C7 H7B 111.5(3) . . ?
F2 C7 H7B 101.9(3) . . ?
F1 C7 H7B 1.93(12) . . ?
C7 C7 H7B 108.7(3) 3_677 . ?
H7A C7 H7B 106.9(3) . . ?
C7 O1 C4 120.1(3) . . ?
_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full 25.52
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max 1.200
_refine_diff_density_min -0.538
_refine_diff_density_rms 0.102
data_jm3
_database_code_depnum_ccdc_archive 'CCDC 656778'
#TrackingRef '4429_web_deposit_cif_file_1_ScottIacono_1298927023.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C16 H14 F2 O4'
_chemical_formula_weight 308.27
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'
O O 0.0106 0.0060 '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'
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M Pbca
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
_cell_length_a 10.434(2)
_cell_length_b 7.7903(16)
_cell_length_c 17.852(4)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1451.0(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 153(2)
_cell_measurement_reflns_used 2772
_cell_measurement_theta_min 3.0034
_cell_measurement_theta_max 26.3607
_exptl_crystal_description rod
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.48
_exptl_crystal_size_mid 0.17
_exptl_crystal_size_min 0.12
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.411
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 640
_exptl_absorpt_coefficient_mu 0.117
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9458
_exptl_absorpt_correction_T_max 0.9861
_exptl_absorpt_process_details 'Jacobson, R., (1998)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 153(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Sealed Tube'
_diffrn_radiation_monochromator 'Graphite Monochromator'
_diffrn_radiation_detector CCD
_diffrn_measurement_device
;
Mercury CCD
;
_diffrn_detector_area_resol_mean 14.6306
_diffrn_measurement_method omega
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_measurement_details
;
scan:
Number of images: 260
Slice: -40.0000 - 90.0000
Image width: 0.5000
Exp time: 80.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 45.0000
Phi: 0.0000
XTD: 27.7129
2theta: -0.1763
scan:
Number of images: 220
Slice: -30.0000 - 80.0000
Image width: 0.5000
Exp time: 80.0000
Rotation axis: Omega
Omega: 0.0000
Chi: 45.0000
Phi: 90.0000
XTD: 27.7129
2theta: -0.1763
;
_diffrn_measurement_device_details
;
AFC8: Eulerian 3 circle
;
_diffrn_standards_number 0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_decay_% 0
_diffrn_reflns_number 8770
_diffrn_reflns_av_R_equivalents 0.0520
_diffrn_reflns_av_sigmaI/netI 0.0277
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 21
_diffrn_reflns_theta_min 3.00
_diffrn_reflns_theta_max 25.04
_reflns_number_total 1270
_reflns_number_gt 1032
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker XSCANS'
_computing_cell_refinement 'Bruker XSCANS'
_computing_data_reduction 'Bruker SHELXTL'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_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^)+(0.1431P)^2^+1.4540P] 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 SHELXL
_refine_ls_extinction_coef ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 1270
_refine_ls_number_parameters 102
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1011
_refine_ls_R_factor_gt 0.0875
_refine_ls_wR_factor_ref 0.2567
_refine_ls_wR_factor_gt 0.2396
_refine_ls_goodness_of_fit_ref 1.086
_refine_ls_restrained_S_all 1.086
_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
O1 O 0.4066(3) 0.1559(3) 0.54999(14) 0.0571(9) Uani 1 1 d . . .
O2 O 0.3397(3) 0.1629(3) 0.85712(14) 0.0561(9) Uani 1 1 d . . .
C1 C 0.3657(3) 0.1538(3) 0.78168(18) 0.0421(9) Uani 1 1 d . . .
C2 C 0.2801(3) 0.2409(4) 0.73563(19) 0.0454(9) Uani 1 1 d . . .
H2 H 0.2091 0.3017 0.7573 0.054 Uiso 1 1 calc R . .
C3 C 0.2966(3) 0.2402(4) 0.6593(2) 0.0478(10) Uani 1 1 d . . .
H3 H 0.2382 0.3013 0.6275 0.057 Uiso 1 1 calc R . .
C4 C 0.3982(3) 0.1505(4) 0.62889(18) 0.0421(9) Uani 1 1 d . . .
C5 C 0.4840(3) 0.0643(4) 0.67354(18) 0.0432(9) Uani 1 1 d . . .
H5 H 0.5545 0.0034 0.6515 0.052 Uiso 1 1 calc R . .
C6 C 0.4681(3) 0.0659(4) 0.75047(18) 0.0419(9) Uani 1 1 d . . .
H6 H 0.5277 0.0063 0.7821 0.050 Uiso 1 1 calc R . .
C7 C 0.4974(5) 0.0663(7) 0.5164(2) 0.0837(17) Uani 1 1 d . . .
C8 C 0.4112(4) 0.0544(5) 0.9051(2) 0.0632(11) Uani 1 1 d . . .
H8A H 0.4036 -0.0623 0.8884 0.095 Uiso 1 1 calc R . .
H8B H 0.3788 0.0638 0.9553 0.095 Uiso 1 1 calc R . .
H8C H 0.4997 0.0880 0.9042 0.095 Uiso 1 1 calc R . .
F1 F 0.6186(3) 0.1557(4) 0.50969(19) 0.0984(12) 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
O1 0.0651(16) 0.0559(15) 0.0502(15) 0.0029(11) 0.0030(11) 0.0190(12)
O2 0.0671(17) 0.0471(14) 0.0542(16) -0.0053(10) 0.0135(12) 0.0074(11)
C1 0.0449(17) 0.0305(15) 0.0509(19) -0.0055(12) 0.0096(13) -0.0046(12)
C2 0.0414(16) 0.0333(15) 0.062(2) -0.0048(14) 0.0073(13) 0.0021(12)
C3 0.0422(17) 0.0337(16) 0.068(2) -0.0002(14) 0.0002(14) 0.0045(13)
C4 0.0442(17) 0.0355(16) 0.0466(18) 0.0005(12) 0.0039(13) 0.0022(12)
C5 0.0407(16) 0.0392(16) 0.0496(18) -0.0009(13) 0.0054(13) 0.0039(12)
C6 0.0423(16) 0.0344(15) 0.0492(18) -0.0008(12) 0.0031(13) -0.0003(12)
C7 0.107(4) 0.090(3) 0.053(2) 0.005(2) 0.001(2) 0.049(3)
C8 0.078(3) 0.065(2) 0.046(2) -0.0056(17) 0.0008(17) 0.006(2)
F1 0.0727(18) 0.092(2) 0.130(3) 0.0228(17) -0.0160(15) -0.0363(15)
_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
O1 C7 1.321(5) . ?
O1 C4 1.412(4) . ?
O2 C1 1.375(4) . ?
O2 C8 1.416(5) . ?
C1 C6 1.387(4) . ?
C1 C2 1.391(5) . ?
C2 C3 1.373(5) . ?
C2 H2 0.9600 . ?
C3 C4 1.381(4) . ?
C3 H3 0.9600 . ?
C4 C5 1.373(5) . ?
C5 C6 1.383(5) . ?
C5 H5 0.9600 . ?
C6 H6 0.9600 . ?
C7 C7 1.189(10) 5_656 ?
C7 F1 1.449(7) . ?
C8 H8A 0.9599 . ?
C8 H8B 0.9599 . ?
C8 H8C 0.9599 . ?
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
C7 O1 C4 118.7(3) . . ?
C1 O2 C8 117.3(3) . . ?
O2 C1 C6 124.8(3) . . ?
O2 C1 C2 115.3(3) . . ?
C6 C1 C2 119.9(3) . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 O1 123.6(3) . . ?
C3 C4 O1 115.1(3) . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C7 C7 O1 135.7(8) 5_656 . ?
C7 C7 F1 109.7(6) 5_656 . ?
O1 C7 F1 114.2(4) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full 25.04
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max 0.697
_refine_diff_density_min -0.533
_refine_diff_density_rms 0.066
# Attachment '4430_web_deposit_cif_file_2_ScottIacono_1298927023.cif'
_publ_section_references
;
Jacobson, R. (1998). REQAB. Version 1.1. Molecular Structure
Corporation, The Woodlands, Texas, USA.
Molecular Structure Corporation & Rigaku (2006). CrystalClear MSC, The
Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). SHELXTL.Version 6.10 Acta Cryst. A64, 112-122.
;