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#$Date: 2019-11-25 11:30:28 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240766 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/02/4130264.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_4130264
loop_
_publ_author_name
'Landry, Matthew L.'
'Hu, Dennis X.'
'McKenna, Grace M.'
'Burns, Noah Z.'
_publ_section_title
;
 Catalytic Enantioselective Dihalogenation and the Selective Synthesis of
 (-)-Deschloromytilipin A and (-)-Danicalipin A.
;
_journal_issue                   15
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5150
_journal_page_last               5158
_journal_paper_doi               10.1021/jacs.6b01643
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H16 Br6 O3'
_chemical_formula_sum            'C15 H16 Br6 O3'
_chemical_formula_weight         723.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 110.597(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.9618(12)
_cell_length_b                   5.2143(3)
_cell_length_c                   18.6577(11)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.33
_cell_volume                     2000.0(2)
_computing_cell_refinement       'Bruker SAINT v8.34A'
_computing_data_collection       'Bruker APEX-II v2014-11.0'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa X8-APEX-II'
_diffrn_measurement_method       'combination of ω and φ-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  0.0346
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            27414
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.397
_diffrn_reflns_theta_min         1.913
_exptl_absorpt_coefficient_mu    12.056
_exptl_absorpt_correction_T_max  0.7656
_exptl_absorpt_correction_T_min  0.1116
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2014/5 (Sheldrick, 2014)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.404
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 1997 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         4981
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0197
_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)+(0.0193P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0399
_refine_ls_wR_factor_ref         0.0407
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4685
_reflns_number_total             4981
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b01643_si_005.cif
_cod_data_source_block           su1502
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4130264
_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   0.163
_shelx_estimated_absorpt_t_max   0.613
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Br1 Br 0.47440(2) 0.65585(11) 0.90150(2) 0.03398(12) Uani 1 1 d . .
Br2 Br 0.51740(2) 0.95214(8) 0.75642(2) 0.02088(9) Uani 1 1 d . .
Br3 Br 0.47275(2) 0.43403(7) 0.60224(2) 0.01655(9) Uani 1 1 d . .
Br4 Br 0.30433(2) 1.01121(7) 0.50899(2) 0.01333(8) Uani 1 1 d . .
Br5 Br 0.41439(2) 0.96521(7) 0.41677(2) 0.01678(8) Uani 1 1 d . .
Br6 Br 0.36092(3) 0.07207(15) -0.00528(3) 0.0613(2) Uani 1 1 d . .
O1 O 0.34707(13) 0.5534(6) 0.65175(16) 0.0191(6) Uani 1 1 d . .
H1O H 0.320(2) 0.604(11) 0.663(3) 0.048(18) Uiso 1 1 d . .
O2 O 0.32485(12) 0.5255(5) 0.31519(15) 0.0172(6) Uani 1 1 d . .
O3 O 0.24749(13) 0.2235(6) 0.28928(17) 0.0236(7) Uani 1 1 d . .
C1 C 0.3905(2) 1.0288(9) 0.8071(3) 0.0327(11) Uani 1 1 d . .
H1A H 0.3674 1.0305 0.8435 0.049 Uiso 1 1 calc R U
H1B H 0.3610 1.0848 0.7568 0.049 Uiso 1 1 calc R U
H1C H 0.4278 1.1454 0.8250 0.049 Uiso 1 1 calc R U
C2 C 0.41410(19) 0.7597(9) 0.8012(2) 0.0211(9) Uani 1 1 d . .
H2A H 0.3755 0.6438 0.7884 0.025 Uiso 1 1 calc R U
C3 C 0.44489(18) 0.7162(7) 0.7408(2) 0.0163(8) Uani 1 1 d . .
H3A H 0.4618 0.5366 0.7458 0.020 Uiso 1 1 calc R U
C4 C 0.39423(17) 0.7498(7) 0.6613(2) 0.0140(8) Uani 1 1 d . .
H4A H 0.3724 0.9193 0.6594 0.017 Uiso 1 1 calc R U
C5 C 0.41778(17) 0.7350(7) 0.5935(2) 0.0124(7) Uani 1 1 d . .
H5A H 0.4430 0.8932 0.5920 0.015 Uiso 1 1 calc R U
C6 C 0.36048(16) 0.7098(7) 0.5186(2) 0.0120(7) Uani 1 1 d . .
H6A H 0.3348 0.5580 0.5245 0.014 Uiso 1 1 calc R U
C7 C 0.37292(17) 0.6707(7) 0.4449(2) 0.0130(7) Uani 1 1 d . .
H7A H 0.4030 0.5210 0.4523 0.016 Uiso 1 1 calc R U
C8 C 0.31062(17) 0.6053(8) 0.3808(2) 0.0184(8) Uani 1 1 d . .
H8A H 0.2878 0.4660 0.3972 0.022 Uiso 1 1 calc R U
H8B H 0.2818 0.7572 0.3678 0.022 Uiso 1 1 calc R U
C9 C 0.28933(18) 0.3348(7) 0.2732(2) 0.0166(8) Uani 1 1 d . .
C10 C 0.30689(18) 0.2766(8) 0.2062(2) 0.0169(8) Uani 1 1 d . .
C11 C 0.35305(18) 0.4205(9) 0.1888(2) 0.0226(9) Uani 1 1 d . .
H11A H 0.3744 0.5585 0.2211 0.027 Uiso 1 1 calc R U
C12 C 0.3680(2) 0.3635(9) 0.1246(3) 0.0301(11) Uani 1 1 d . .
H12A H 0.3988 0.4635 0.1118 0.036 Uiso 1 1 calc R U
C13 C 0.3374(2) 0.1604(11) 0.0796(2) 0.0331(11) Uani 1 1 d . .
C14 C 0.2917(2) 0.0148(11) 0.0954(3) 0.0365(12) Uani 1 1 d . .
H14A H 0.2713 -0.1254 0.0634 0.044 Uiso 1 1 calc R U
C15 C 0.2757(2) 0.0762(9) 0.1588(3) 0.0286(10) Uani 1 1 d . .
H15A H 0.2433 -0.0196 0.1699 0.034 Uiso 1 1 calc R U
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
C9 O2 C8 117.5(3)
C1 C2 C3 116.5(4)
C1 C2 Br1 108.7(3)
C3 C2 Br1 109.9(3)
C4 C3 C2 110.0(3)
C4 C3 Br2 110.6(3)
C2 C3 Br2 110.4(3)
O1 C4 C3 106.9(3)
O1 C4 C5 107.6(3)
C3 C4 C5 117.2(3)
C6 C5 C4 110.7(3)
C6 C5 Br3 107.2(2)
C4 C5 Br3 110.5(2)
C7 C6 C5 119.5(3)
C7 C6 Br4 109.5(2)
C5 C6 Br4 107.7(2)
C8 C7 C6 110.5(3)
C8 C7 Br5 110.1(3)
C6 C7 Br5 113.0(2)
O2 C8 C7 109.6(3)
O3 C9 O2 123.4(4)
O3 C9 C10 124.3(4)
O2 C9 C10 112.3(3)
C15 C10 C11 119.7(4)
C15 C10 C9 118.9(4)
C11 C10 C9 121.4(4)
C12 C11 C10 120.2(4)
C13 C12 C11 118.9(4)
C12 C13 C14 122.2(4)
C12 C13 Br6 118.9(4)
C14 C13 Br6 118.8(4)
C13 C14 C15 118.7(5)
C10 C15 C14 120.3(4)
C4 O1 H1O 109(4)
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
C1 C2 H2A 107.1
C3 C2 H2A 107.1
Br1 C2 H2A 107.1
C4 C3 H3A 108.6
C2 C3 H3A 108.6
Br2 C3 H3A 108.6
O1 C4 H4A 108.3
C3 C4 H4A 108.3
C5 C4 H4A 108.3
C6 C5 H5A 109.5
C4 C5 H5A 109.5
Br3 C5 H5A 109.5
C7 C6 H6A 106.5
C5 C6 H6A 106.5
Br4 C6 H6A 106.5
C8 C7 H7A 107.7
C6 C7 H7A 107.7
Br5 C7 H7A 107.7
O2 C8 H8A 109.8
C7 C8 H8A 109.8
O2 C8 H8B 109.8
C7 C8 H8B 109.8
H8A C8 H8B 108.2
C12 C11 H11A 119.9
C10 C11 H11A 119.9
C13 C12 H12A 120.5
C11 C12 H12A 120.5
C13 C14 H14A 120.6
C15 C14 H14A 120.6
C10 C15 H15A 119.9
C14 C15 H15A 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.951(4)
Br2 C3 1.951(4)
Br3 C5 1.951(3)
Br4 C6 1.966(3)
Br5 C7 1.950(4)
Br6 C13 1.887(4)
O1 C4 1.422(4)
O2 C9 1.334(4)
O2 C8 1.428(4)
O3 C9 1.210(4)
C1 C2 1.513(6)
C2 C3 1.520(5)
C3 C4 1.519(5)
C4 C5 1.529(5)
C5 C6 1.521(5)
C6 C7 1.507(5)
C7 C8 1.506(5)
C9 C10 1.464(5)
C10 C15 1.385(6)
C10 C11 1.389(5)
C11 C12 1.381(6)
C12 C13 1.371(7)
C13 C14 1.372(7)
C14 C15 1.385(6)
O1 H1O 0.76(5)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 H2A 1.0000
C3 H3A 1.0000
C4 H4A 1.0000
C5 H5A 1.0000
C6 H6A 1.0000
C7 H7A 1.0000
C8 H8A 0.9900
C8 H8B 0.9900
C11 H11A 0.9500
C12 H12A 0.9500
C14 H14A 0.9500
C15 H15A 0.9500
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
O1 H1O O3 0.76(5) 2.06(5) 2.814(4) 172(6) 4_556
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
C1 C2 C3 C4 -66.2(5)
Br1 C2 C3 C4 169.6(3)
C1 C2 C3 Br2 56.1(4)
Br1 C2 C3 Br2 -68.1(3)
C2 C3 C4 O1 -64.1(4)
Br2 C3 C4 O1 173.7(2)
C2 C3 C4 C5 175.1(3)
Br2 C3 C4 C5 52.9(4)
O1 C4 C5 C6 46.4(4)
C3 C4 C5 C6 166.8(3)
O1 C4 C5 Br3 -72.2(3)
C3 C4 C5 Br3 48.3(4)
C4 C5 C6 C7 -175.1(3)
Br3 C5 C6 C7 -54.5(4)
C4 C5 C6 Br4 59.2(3)
Br3 C5 C6 Br4 179.79(16)
C5 C6 C7 C8 170.2(3)
Br4 C6 C7 C8 -65.0(3)
C5 C6 C7 Br5 -65.9(4)
Br4 C6 C7 Br5 59.0(3)
C9 O2 C8 C7 142.2(3)
C6 C7 C8 O2 -169.9(3)
Br5 C7 C8 O2 64.5(4)
C8 O2 C9 O3 -2.1(5)
C8 O2 C9 C10 178.0(3)
O3 C9 C10 C15 -2.3(6)
O2 C9 C10 C15 177.6(4)
O3 C9 C10 C11 176.6(4)
O2 C9 C10 C11 -3.5(5)
C15 C10 C11 C12 -0.2(6)
C9 C10 C11 C12 -179.0(4)
C10 C11 C12 C13 -1.3(7)
C11 C12 C13 C14 1.3(7)
C11 C12 C13 Br6 -176.9(3)
C12 C13 C14 C15 0.2(7)
Br6 C13 C14 C15 178.4(4)
C11 C10 C15 C14 1.7(7)
C9 C10 C15 C14 -179.4(4)
C13 C14 C15 C10 -1.7(7)
