#------------------------------------------------------------------------------
#$Date: 2015-07-09 01:06:54 +0300 (Thu, 09 Jul 2015) $
#$Revision: 141402 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/03/1520317.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_1520317
loop_
_publ_author_name
'Roßbach, Jan'
'Harms, Klaus'
'Koert, Ulrich'
_publ_section_title
;
 α-Crotyl-α-difluoroboranyloxy-amides: Structure and Reactivity of
 Isolable Intermediates in Stereospecific α-Ketol Rearrangements.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3122
_journal_page_last               3125
_journal_paper_doi               10.1021/acs.orglett.5b01427
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C8 H11 Br O4'
_chemical_formula_sum            'C8 H11 Br O4'
_chemical_formula_weight         251.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.753(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8688(4)
_cell_length_b                   18.0772(8)
_cell_length_c                   6.0396(3)
_cell_measurement_reflns_used    5075
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.2291
_cell_measurement_theta_min      2.2532
_cell_volume                     964.96(8)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER APEX2 2014.9-0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT V2014/1 (Bruker AXS Inc., 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 QUEST area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            12918
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.245
_diffrn_reflns_theta_min         2.253
_diffrn_source                   'microfocus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.240
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.42
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.802
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0236
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0242P)²+0.6873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0510
_refine_ls_wR_factor_ref         0.0538
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1505
_reflns_number_total             1751
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5b01427_si_002.cif
_cod_data_source_block           JR21551_0m
_cod_depositor_comments
'Adding full bibliography for 1520305--1520319.cif.'
_cod_database_code               1520317
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.282
_shelx_estimated_absorpt_t_max   0.849
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 1.0498(3) 0.34153(14) 0.3972(4) 0.0232(5) Uani 1 1 d . .
H1A H 1.1602 0.3459 0.4028 0.035 Uiso 1 1 calc R U
H1B H 1.0182 0.2945 0.3272 0.035 Uiso 1 1 calc R U
H1C H 1.0176 0.3432 0.5485 0.035 Uiso 1 1 calc R U
C2 C 0.9790(2) 0.40388(13) 0.2654(3) 0.0177(5) Uani 1 1 d . .
C3 C 0.8118(2) 0.39830(12) 0.1802(3) 0.0135(4) Uani 1 1 d . .
C4 C 0.7034(2) 0.37395(12) 0.3500(3) 0.0126(4) Uani 1 1 d . .
H4 H 0.7551 0.3345 0.4443 0.015 Uiso 1 1 calc R U
C5 C 0.5750(2) 0.33704(12) 0.2024(4) 0.0144(4) Uani 1 1 d . .
H5 H 0.5294 0.2965 0.2876 0.017 Uiso 1 1 calc R U
C6 C 0.4518(2) 0.38828(12) 0.1091(4) 0.0172(5) Uani 1 1 d . .
H6A H 0.4970 0.4292 0.0279 0.021 Uiso 1 1 calc R U
H6B H 0.3993 0.4100 0.2322 0.021 Uiso 1 1 calc R U
C7 C 0.7877(2) 0.33711(12) 0.0045(4) 0.0149(4) Uani 1 1 d . .
C8 C 0.6563(3) 0.43457(13) 0.5040(4) 0.0210(5) Uani 1 1 d . .
H8A H 0.5780 0.4157 0.5945 0.031 Uiso 1 1 calc R U
H8B H 0.6162 0.4767 0.4156 0.031 Uiso 1 1 calc R U
H8C H 0.7442 0.4505 0.6013 0.031 Uiso 1 1 calc R U
O1 O 1.04807(19) 0.45893(10) 0.2200(3) 0.0281(4) Uani 1 1 d . .
O2 O 0.7604(2) 0.46474(9) 0.0769(3) 0.0179(4) Uani 1 1 d . .
H2 H 0.826(3) 0.4841(16) 0.042(5) 0.030(9) Uiso 1 1 d . .
O3 O 0.65181(17) 0.30508(9) 0.0204(3) 0.0171(3) Uani 1 1 d . .
O4 O 0.86921(19) 0.31941(9) -0.1354(3) 0.0223(4) Uani 1 1 d . .
Br1 Br 0.30660(3) 0.33512(2) -0.09145(4) 0.02551(10) 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'
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
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O1 C2 C1 123.0(2)
O1 C2 C3 118.1(2)
C1 C2 C3 118.90(19)
O2 C3 C4 110.09(17)
O2 C3 C2 111.14(18)
C4 C3 C2 116.04(17)
O2 C3 C7 106.63(16)
C4 C3 C7 101.35(17)
C2 C3 C7 110.82(18)
C8 C4 C3 115.08(18)
C8 C4 C5 116.09(18)
C3 C4 C5 102.27(16)
C8 C4 H4 107.6
C3 C4 H4 107.6
C5 C4 H4 107.6
O3 C5 C6 109.33(17)
O3 C5 C4 103.83(16)
C6 C5 C4 115.41(18)
O3 C5 H5 109.3
C6 C5 H5 109.3
C4 C5 H5 109.3
C5 C6 Br1 110.56(15)
C5 C6 H6A 109.5
Br1 C6 H6A 109.5
C5 C6 H6B 109.5
Br1 C6 H6B 109.5
H6A C6 H6B 108.1
O4 C7 O3 122.0(2)
O4 C7 C3 128.4(2)
O3 C7 C3 109.55(17)
C4 C8 H8A 109.5
C4 C8 H8B 109.5
H8A C8 H8B 109.5
C4 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C3 O2 H2 108(2)
C7 O3 C5 111.08(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.488(3)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 O1 1.212(3)
C2 C3 1.532(3)
C3 O2 1.411(3)
C3 C4 1.528(3)
C3 C7 1.536(3)
C4 C8 1.518(3)
C4 C5 1.539(3)
C4 H4 1.0000
C5 O3 1.459(3)
C5 C6 1.506(3)
C5 H5 1.0000
C6 Br1 1.947(2)
C6 H6A 0.9900
C6 H6B 0.9900
C7 O4 1.200(3)
C7 O3 1.347(3)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
O2 H2 0.72(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.72(3) 2.21(3) 2.627(2) 117(3) .
O2 H2 O1 0.72(3) 2.26(3) 2.917(2) 152(3) 3_765
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
O1 C2 C3 O2 -6.1(3)
C1 C2 C3 O2 174.57(19)
O1 C2 C3 C4 -132.9(2)
C1 C2 C3 C4 47.8(3)
O1 C2 C3 C7 112.2(2)
C1 C2 C3 C7 -67.0(3)
O2 C3 C4 C8 -46.6(2)
C2 C3 C4 C8 80.7(2)
C7 C3 C4 C8 -159.19(18)
O2 C3 C4 C5 80.2(2)
C2 C3 C4 C5 -152.51(18)
C7 C3 C4 C5 -32.4(2)
C8 C4 C5 O3 158.49(18)
C3 C4 C5 O3 32.4(2)
C8 C4 C5 C6 38.9(3)
C3 C4 C5 C6 -87.3(2)
O3 C5 C6 Br1 59.05(19)
C4 C5 C6 Br1 175.62(14)
O2 C3 C7 O4 84.6(3)
C4 C3 C7 O4 -160.2(2)
C2 C3 C7 O4 -36.5(3)
O2 C3 C7 O3 -92.8(2)
C4 C3 C7 O3 22.4(2)
C2 C3 C7 O3 146.16(17)
O4 C7 O3 C5 -179.5(2)
C3 C7 O3 C5 -1.9(2)
C6 C5 O3 C7 104.2(2)
C4 C5 O3 C7 -19.5(2)
