#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:44:39 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180313 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/27/7152795.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7152795
loop_
_publ_author_name
'Yang, Yan'
'Gao, Meng'
'Shu, Wen-Ming'
'Wu, Liu-Ming'
'Zhang, Dong-Xue'
'Wu, An-Xin'
_publ_section_title
;
 Synthesis of α-iodoketals from methyl ketones via sustainable and
 orthogonal tandem catalysis.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1226
_journal_page_last               1233
_journal_paper_doi               10.1039/c2ob27028e
_journal_volume                  11
_journal_year                    2013
_chemical_formula_sum            'C17 H13 F O2'
_chemical_formula_weight         268.27
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.0702(12)
_cell_length_b                   15.872(2)
_cell_length_c                   19.619(3)
_cell_measurement_reflns_used    5759
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.71
_cell_measurement_theta_min      2.25
_cell_volume                     2824.4(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20476
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.9892
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0034(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0677P)²+0.4112P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1478
_reflns_number_gt                2328
_reflns_number_total             3242
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob27028e.txt
_cod_data_source_block           mo_120314f_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2824.3(6)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7152795
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'
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
C1 C 1.32606(18) 0.46248(11) 0.15177(10) 0.0700(5) Uani 1 1 d .
C2 C 1.35457(19) 0.45198(14) 0.08452(11) 0.0871(6) Uani 1 1 d .
H2 H 1.4482 0.4621 0.0670 0.104 Uiso 1 1 calc R
C3 C 1.24111(18) 0.42580(13) 0.04265(9) 0.0736(5) Uani 1 1 d .
H3 H 1.2596 0.4182 -0.0036 0.088 Uiso 1 1 calc R
C4 C 1.10085(16) 0.41055(9) 0.06732(8) 0.0575(4) Uani 1 1 d .
C5 C 1.0790(2) 0.42368(16) 0.13678(10) 0.0909(6) Uani 1 1 d .
H5 H 0.9856 0.4149 0.1550 0.109 Uiso 1 1 calc R
C6 C 1.1911(2) 0.44926(15) 0.17920(10) 0.0882(6) Uani 1 1 d .
H6 H 1.1745 0.4573 0.2255 0.106 Uiso 1 1 calc R
C7 C 0.98929(18) 0.38192(10) 0.01901(8) 0.0613(4) Uani 1 1 d .
H7 H 1.0224 0.3759 -0.0256 0.074 Uiso 1 1 calc R
C8 C 0.84660(17) 0.36286(9) 0.02856(8) 0.0559(4) Uani 1 1 d .
C9 C 0.7499(2) 0.33339(11) -0.02718(9) 0.0703(5) Uani 1 1 d .
C10 C 0.8121(3) 0.31360(17) -0.09598(11) 0.1029(7) Uani 1 1 d .
H10A H 0.7341 0.2958 -0.1258 0.154 Uiso 1 1 calc R
H10B H 0.8836 0.2693 -0.0919 0.154 Uiso 1 1 calc R
H10C H 0.8585 0.3630 -0.1144 0.154 Uiso 1 1 calc R
C11 C 0.76552(16) 0.36997(9) 0.09519(8) 0.0545(4) Uani 1 1 d .
C12 C 0.73823(16) 0.29153(9) 0.13380(7) 0.0532(4) Uani 1 1 d .
C13 C 0.6350(2) 0.29197(14) 0.18599(9) 0.0813(5) Uani 1 1 d .
H13 H 0.5860 0.3416 0.1971 0.098 Uiso 1 1 calc R
C14 C 0.6053(3) 0.2196(2) 0.22097(12) 0.1159(9) Uani 1 1 d .
H14 H 0.5348 0.2200 0.2554 0.139 Uiso 1 1 calc R
C15 C 0.6776(4) 0.14727(19) 0.20599(14) 0.1198(10) Uani 1 1 d .
H15 H 0.6568 0.0985 0.2304 0.144 Uiso 1 1 calc R
C16 C 0.7820(3) 0.14516(12) 0.15483(12) 0.0970(7) Uani 1 1 d .
H16 H 0.8314 0.0953 0.1449 0.116 Uiso 1 1 calc R
C17 C 0.8125(2) 0.21765(9) 0.11842(8) 0.0657(4) Uani 1 1 d .
H17 H 0.8826 0.2168 0.0838 0.079 Uiso 1 1 calc R
F1 F 1.43588(11) 0.48813(8) 0.19407(7) 0.1018(4) Uani 1 1 d .
O1 O 0.72114(14) 0.43788(7) 0.11484(7) 0.0823(4) Uani 1 1 d .
O2 O 0.61893(15) 0.32480(10) -0.01538(8) 0.0940(5) Uani 1 1 d .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 122.73(17)
C6 C1 F1 117.82(17)
C2 C1 F1 119.45(15)
C1 C2 C3 118.30(16)
C1 C2 H2 120.8
C3 C2 H2 120.8
C2 C3 C4 122.02(16)
C2 C3 H3 119.0
C4 C3 H3 119.0
C3 C4 C5 116.58(15)
C3 C4 C7 117.72(14)
C5 C4 C7 125.70(14)
C6 C5 C4 122.08(16)
C6 C5 H5 119.0
C4 C5 H5 119.0
C1 C6 C5 118.28(18)
C1 C6 H6 120.9
C5 C6 H6 120.9
C8 C7 C4 130.40(14)
C8 C7 H7 114.8
C4 C7 H7 114.8
C7 C8 C9 122.69(15)
C7 C8 C11 125.16(14)
C9 C8 C11 112.13(14)
O2 C9 C8 118.27(17)
O2 C9 C10 121.03(18)
C8 C9 C10 120.70(17)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O1 C11 C12 121.98(14)
O1 C11 C8 120.33(14)
C12 C11 C8 117.65(12)
C17 C12 C13 119.55(16)
C17 C12 C11 121.30(14)
C13 C12 C11 119.14(15)
C14 C13 C12 120.0(2)
C14 C13 H13 120.0
C12 C13 H13 120.0
C15 C14 C13 120.6(2)
C15 C14 H14 119.7
C13 C14 H14 119.7
C14 C15 C16 120.7(2)
C14 C15 H15 119.6
C16 C15 H15 119.6
C15 C16 C17 119.6(2)
C15 C16 H16 120.2
C17 C16 H16 120.2
C16 C17 C12 119.62(19)
C16 C17 H17 120.2
C12 C17 H17 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.354(2)
C1 C2 1.355(3)
C1 F1 1.3589(19)
C2 C3 1.381(3)
C2 H2 0.9300
C3 C4 1.383(2)
C3 H3 0.9300
C4 C5 1.393(2)
C4 C7 1.459(2)
C5 C6 1.375(3)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.342(2)
C7 H7 0.9300
C8 C9 1.478(2)
C8 C11 1.504(2)
C9 O2 1.218(2)
C9 C10 1.496(3)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 O1 1.2135(17)
C11 C12 1.478(2)
C12 C17 1.386(2)
C12 C13 1.387(2)
C13 C14 1.365(3)
C13 H13 0.9300
C14 C15 1.355(4)
C14 H14 0.9300
C15 C16 1.380(4)
C15 H15 0.9300
C16 C17 1.382(3)
C16 H16 0.9300
C17 H17 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 -0.7(3)
F1 C1 C2 C3 179.95(18)
C1 C2 C3 C4 0.2(3)
C2 C3 C4 C5 0.6(3)
C2 C3 C4 C7 -179.13(18)
C3 C4 C5 C6 -0.9(3)
C7 C4 C5 C6 178.7(2)
C2 C1 C6 C5 0.4(3)
F1 C1 C6 C5 179.7(2)
C4 C5 C6 C1 0.5(4)
C3 C4 C7 C8 -179.81(17)
C5 C4 C7 C8 0.5(3)
C4 C7 C8 C9 -179.13(15)
C4 C7 C8 C11 2.0(3)
C7 C8 C9 O2 -173.48(16)
C11 C8 C9 O2 5.5(2)
C7 C8 C9 C10 7.3(3)
C11 C8 C9 C10 -173.72(17)
C7 C8 C11 O1 79.6(2)
C9 C8 C11 O1 -99.31(17)
C7 C8 C11 C12 -102.41(17)
C9 C8 C11 C12 78.64(17)
O1 C11 C12 C17 -167.28(15)
C8 C11 C12 C17 14.8(2)
O1 C11 C12 C13 13.4(2)
C8 C11 C12 C13 -164.53(15)
C17 C12 C13 C14 -1.2(3)
C11 C12 C13 C14 178.18(18)
C12 C13 C14 C15 1.1(4)
C13 C14 C15 C16 -0.4(4)
C14 C15 C16 C17 -0.2(4)
C15 C16 C17 C12 0.1(3)
C13 C12 C17 C16 0.6(2)
C11 C12 C17 C16 -178.77(15)
