#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/43/1504312.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_1504312
loop_
_publ_author_name
'Zhao, Jun-Feng'
'Tjan, Teguh-Budiono W'
'Tan, Boon-Hong'
'Loh, Teck-Peng'
_publ_section_title
;
 Highly enantioselective ketone-ene reactions of trifluoropyruvate:
 significant counterion effect of the In(III)-pybox complex.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5714
_journal_page_last               5716
_journal_paper_doi               10.1021/ol902507x
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H12 Br F3 O3'
_chemical_formula_sum            'C13 H12 Br F3 O3'
_chemical_formula_weight         353.14
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   6.8098(4)
_cell_length_b                   8.2633(6)
_cell_length_c                   23.9486(18)
_cell_measurement_reflns_used    3043
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.82
_cell_measurement_theta_min      2.61
_cell_volume                     1347.62(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0678
_diffrn_reflns_av_sigmaI/netI    0.1102
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            16389
_diffrn_reflns_theta_full        34.86
_diffrn_reflns_theta_max         34.86
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    3.090
_exptl_absorpt_correction_T_max  0.3864
_exptl_absorpt_correction_T_min  0.3569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.032(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         5711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0030P)²+0.7733P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.1143
_reflns_number_gt                3116
_reflns_number_total             5711
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol902507x_si_003.cif
_cod_data_source_block           ltp147
_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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1504312
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'
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
Br1 Br 0.94731(6) 0.71197(6) 0.220908(17) 0.05002(14) Uani 1 1 d .
C1 C 0.7361(4) 0.7100(4) 0.27280(12) 0.0281(6) Uani 1 1 d .
C2 C 0.5785(5) 0.8118(4) 0.26465(12) 0.0291(7) Uani 1 1 d .
H2 H 0.5770 0.8849 0.2341 0.035 Uiso 1 1 calc R
C3 C 0.4220(4) 0.8061(4) 0.30159(11) 0.0254(6) Uani 1 1 d .
H3 H 0.3126 0.8754 0.2960 0.031 Uiso 1 1 calc R
C4 C 0.4230(4) 0.7000(4) 0.34690(10) 0.0205(6) Uani 1 1 d .
C5 C 0.5906(5) 0.6037(4) 0.35454(13) 0.0305(8) Uani 1 1 d .
H5 H 0.5976 0.5341 0.3861 0.037 Uiso 1 1 calc R
C6 C 0.7449(5) 0.6075(5) 0.31749(14) 0.0327(8) Uani 1 1 d .
H6 H 0.8560 0.5398 0.3229 0.039 Uiso 1 1 calc R
C7 C 0.2523(4) 0.6886(4) 0.38587(11) 0.0222(6) Uani 1 1 d .
C8 C 0.1883(5) 0.5456(5) 0.40232(14) 0.0322(8) Uani 1 1 d .
H8A H 0.2508 0.4499 0.3894 0.039 Uiso 1 1 calc R
H8B H 0.0798 0.5383 0.4271 0.039 Uiso 1 1 calc R
C9 C 0.1600(5) 0.8416(4) 0.40653(12) 0.0211(6) Uani 1 1 d .
H9A H 0.0277 0.8168 0.4213 0.025 Uiso 1 1 calc R
H9B H 0.1440 0.9173 0.3748 0.025 Uiso 1 1 calc R
C10 C 0.2816(4) 0.9247(4) 0.45249(12) 0.0187(6) Uani 1 1 d .
C11 C 0.1704(5) 1.0726(4) 0.47445(13) 0.0238(6) Uani 1 1 d .
C12 C 0.4832(4) 0.9773(4) 0.43073(11) 0.0187(6) Uani 1 1 d .
C13 C 0.6516(5) 1.1413(5) 0.36663(14) 0.0311(8) Uani 1 1 d .
H13A H 0.7353 1.1906 0.3952 0.047 Uiso 1 1 calc R
H13B H 0.6254 1.2205 0.3371 0.047 Uiso 1 1 calc R
H13C H 0.7183 1.0470 0.3507 0.047 Uiso 1 1 calc R
F1 F 0.0150(3) 1.0276(3) 0.50451(8) 0.0348(5) Uani 1 1 d .
F2 F 0.2838(3) 1.1617(3) 0.50796(9) 0.0422(6) Uani 1 1 d .
F3 F 0.1057(3) 1.1701(2) 0.43404(8) 0.0358(5) Uani 1 1 d .
O1 O 0.3225(3) 0.8244(3) 0.49810(8) 0.0278(5) Uani 1 1 d .
H1 H 0.2215 0.7712 0.5065 0.042 Uiso 1 1 calc R
O2 O 0.6380(3) 0.9219(3) 0.44621(10) 0.0302(5) Uani 1 1 d .
O3 O 0.4681(3) 1.0910(3) 0.39159(8) 0.0238(4) 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'
Br Br -0.2901 2.4595 '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 121.6(3)
C6 C1 Br1 119.0(2)
C2 C1 Br1 119.5(2)
C1 C2 C3 119.2(3)
C1 C2 H2 120.4
C3 C2 H2 120.4
C2 C3 C4 121.0(3)
C2 C3 H3 119.5
C4 C3 H3 119.5
C3 C4 C5 117.5(3)
C3 C4 C7 121.5(3)
C5 C4 C7 121.1(3)
C6 C5 C4 121.6(3)
C6 C5 H5 119.2
C4 C5 H5 119.2
C1 C6 C5 119.1(3)
C1 C6 H6 120.5
C5 C6 H6 120.5
C8 C7 C4 120.0(3)
C8 C7 C9 121.3(3)
C4 C7 C9 118.7(3)
C7 C8 H8A 120.0
C7 C8 H8B 120.0
H8A C8 H8B 120.0
C7 C9 C10 112.8(3)
C7 C9 H9A 109.0
C10 C9 H9A 109.0
C7 C9 H9B 109.0
C10 C9 H9B 109.0
H9A C9 H9B 107.8
O1 C10 C11 107.7(2)
O1 C10 C12 104.8(2)
C11 C10 C12 109.5(3)
O1 C10 C9 113.6(3)
C11 C10 C9 109.6(3)
C12 C10 C9 111.5(2)
F1 C11 F3 107.3(3)
F1 C11 F2 106.8(2)
F3 C11 F2 107.1(3)
F1 C11 C10 110.9(3)
F3 C11 C10 113.3(2)
F2 C11 C10 111.1(3)
O2 C12 O3 123.5(3)
O2 C12 C10 124.8(2)
O3 C12 C10 111.8(2)
O3 C13 H13A 109.5
O3 C13 H13B 109.5
H13A C13 H13B 109.5
O3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C10 O1 H1 109.5
C12 O3 C13 115.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.901(3)
C1 C6 1.366(5)
C1 C2 1.377(5)
C2 C3 1.386(4)
C2 H2 0.9500
C3 C4 1.395(4)
C3 H3 0.9500
C4 C5 1.403(4)
C4 C7 1.493(4)
C5 C6 1.376(5)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.320(5)
C7 C9 1.496(4)
C8 H8A 0.9500
C8 H8B 0.9500
C9 C10 1.539(4)
C9 H9A 0.9900
C9 H9B 0.9900
C10 O1 1.399(3)
C10 C11 1.531(4)
C10 C12 1.531(4)
C11 F1 1.333(3)
C11 F3 1.334(4)
C11 F2 1.335(4)
C12 O2 1.208(3)
C12 O3 1.331(3)
C13 O3 1.446(4)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
O1 H1 0.8400
