#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/89/1508968.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_1508968
loop_
_publ_author_name
'Keilitz, Juliane'
'Newman, Stephen G.'
'Lautens, Mark'
_publ_section_title
;
 Enantioselective rh-catalyzed domino transformations of
 alkynylcyclohexadienones with organoboron reagents.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1148
_journal_page_last               1151
_journal_paper_doi               10.1021/ol400363f
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H15 Br O2'
_chemical_formula_sum            'C16 H15 Br O2'
_chemical_formula_weight         319.19
_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                   7.3452(9)
_cell_length_b                   9.9405(13)
_cell_length_c                   18.551(2)
_cell_measurement_reflns_used    8999
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.32
_cell_volume                     1354.5(3)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Bruker Triumph'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16628
_diffrn_reflns_theta_full        27.60
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         2.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.029
_exptl_absorpt_correction_T_max  0.6942
_exptl_absorpt_correction_T_min  0.5180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.016(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.922
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0227
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0135P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0374
_refine_ls_wR_factor_ref         0.0381
_reflns_number_gt                2761
_reflns_number_total             3138
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol400363f_si_002.cif
_cod_data_source_block           d1238
_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_database_code               1508968
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'
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 0.46153(3) 0.17225(2) 0.585252(12) 0.03033(6) Uani 1 1 d .
O1 O 0.49936(17) 0.94542(12) 0.31310(7) 0.0217(3) Uani 1 1 d .
O2 O 1.0502(2) 0.62435(13) 0.34514(7) 0.0302(3) Uani 1 1 d .
C1 C 0.5834(2) 0.8308(2) 0.27851(9) 0.0198(4) Uani 1 1 d .
C2 C 0.7761(3) 0.87057(19) 0.26077(10) 0.0234(5) Uani 1 1 d .
H2A H 0.7929 0.9487 0.2321 0.028 Uiso 1 1 calc R
C3 C 0.9231(3) 0.80579(19) 0.28179(10) 0.0243(5) Uani 1 1 d .
H3A H 1.0392 0.8422 0.2703 0.029 Uiso 1 1 calc R
C4 C 0.9136(3) 0.6794(2) 0.32229(9) 0.0220(4) Uani 1 1 d .
C5 C 0.7281(3) 0.61741(18) 0.32962(11) 0.0199(4) Uani 1 1 d .
H5A H 0.7272 0.5592 0.3729 0.024 Uiso 1 1 calc R
H5B H 0.7056 0.5592 0.2872 0.024 Uiso 1 1 calc R
C6 C 0.5726(3) 0.71883(17) 0.33578(10) 0.0164(4) Uani 1 1 d .
H6A H 0.4546 0.6699 0.3297 0.020 Uiso 1 1 calc R
C7 C 0.5665(2) 0.79701(16) 0.40638(10) 0.0174(4) Uani 1 1 d .
C8 C 0.5674(3) 0.94355(18) 0.38593(9) 0.0216(5) Uani 1 1 d .
H8A H 0.4874 0.9962 0.4183 0.026 Uiso 1 1 calc R
H8B H 0.6921 0.9810 0.3882 0.026 Uiso 1 1 calc R
C9 C 0.4781(3) 0.79736(18) 0.21053(10) 0.0274(5) Uani 1 1 d .
H9A H 0.4894 0.8717 0.1761 0.041 Uiso 1 1 calc R
H9B H 0.3495 0.7838 0.2225 0.041 Uiso 1 1 calc R
H9C H 0.5274 0.7150 0.1890 0.041 Uiso 1 1 calc R
C10 C 0.5538(3) 0.75181(19) 0.47341(10) 0.0198(4) Uani 1 1 d .
H10A H 0.5577 0.8183 0.5102 0.024 Uiso 1 1 calc R
C11 C 0.5343(3) 0.61125(18) 0.49844(9) 0.0185(4) Uani 1 1 d .
C12 C 0.4314(3) 0.51698(19) 0.46121(10) 0.0228(5) Uani 1 1 d .
H12A H 0.3730 0.5423 0.4176 0.027 Uiso 1 1 calc R
C13 C 0.4122(3) 0.3864(2) 0.48663(10) 0.0234(5) Uani 1 1 d .
H13A H 0.3432 0.3225 0.4601 0.028 Uiso 1 1 calc R
C14 C 0.4936(2) 0.35061(18) 0.55020(10) 0.0198(5) Uani 1 1 d .
C15 C 0.5935(2) 0.44158(18) 0.58965(11) 0.0225(4) Uani 1 1 d .
H15A H 0.6483 0.4158 0.6339 0.027 Uiso 1 1 calc R
C16 C 0.6130(3) 0.57229(19) 0.56346(10) 0.0215(5) Uani 1 1 d .
H16A H 0.6812 0.6359 0.5905 0.026 Uiso 1 1 calc R
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
C8 O1 C1 104.95(13)
O1 C1 C2 106.96(15)
O1 C1 C9 108.91(14)
C2 C1 C9 110.81(16)
O1 C1 C6 103.95(13)
C2 C1 C6 112.88(15)
C9 C1 C6 112.87(16)
C3 C2 C1 125.31(18)
C3 C2 H2A 117.3
C1 C2 H2A 117.3
C2 C3 C4 122.15(18)
C2 C3 H3A 118.9
C4 C3 H3A 118.9
O2 C4 C3 121.58(18)
O2 C4 C5 122.11(19)
C3 C4 C5 116.19(17)
C4 C5 C6 114.50(16)
C4 C5 H5A 108.6
C6 C5 H5A 108.6
C4 C5 H5B 108.6
C6 C5 H5B 108.6
H5A C5 H5B 107.6
C7 C6 C5 115.01(15)
C7 C6 C1 103.04(14)
C5 C6 C1 112.73(15)
C7 C6 H6A 108.6
C5 C6 H6A 108.6
C1 C6 H6A 108.6
C10 C7 C8 124.38(17)
C10 C7 C6 129.46(15)
C8 C7 C6 106.08(14)
O1 C8 C7 104.32(14)
O1 C8 H8A 110.9
C7 C8 H8A 110.9
O1 C8 H8B 110.9
C7 C8 H8B 110.9
H8A C8 H8B 108.9
C1 C9 H9A 109.5
C1 C9 H9B 109.5
H9A C9 H9B 109.5
C1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C7 C10 C11 128.42(17)
C7 C10 H10A 115.8
C11 C10 H10A 115.8
C12 C11 C16 117.99(17)
C12 C11 C10 122.27(18)
C16 C11 C10 119.65(18)
C13 C12 C11 121.16(18)
C13 C12 H12A 119.4
C11 C12 H12A 119.4
C14 C13 C12 119.44(18)
C14 C13 H13A 120.3
C12 C13 H13A 120.3
C13 C14 C15 121.35(18)
C13 C14 Br1 118.85(14)
C15 C14 Br1 119.78(14)
C14 C15 C16 118.81(19)
C14 C15 H15A 120.6
C16 C15 H15A 120.6
C11 C16 C15 121.23(18)
C11 C16 H16A 119.4
C15 C16 H16A 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C14 1.9031(18)
O1 C8 1.441(2)
O1 C1 1.446(2)
O2 C4 1.219(2)
C1 C2 1.506(2)
C1 C9 1.516(2)
C1 C6 1.541(2)
C2 C3 1.316(3)
C2 H2A 0.9500
C3 C4 1.466(3)
C3 H3A 0.9500
C4 C5 1.501(2)
C5 C6 1.528(2)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.523(2)
C6 H6A 1.0000
C7 C10 1.326(2)
C7 C8 1.505(2)
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 C11 1.479(2)
C10 H10A 0.9500
C11 C12 1.388(3)
C11 C16 1.392(3)
C12 C13 1.388(3)
C12 H12A 0.9500
C13 C14 1.369(3)
C13 H13A 0.9500
C14 C15 1.375(3)
C15 C16 1.395(3)
C15 H15A 0.9500
C16 H16A 0.9500
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
C8 O1 C1 C2 -77.96(16)
C8 O1 C1 C9 162.23(15)
C8 O1 C1 C6 41.68(17)
O1 C1 C2 C3 123.9(2)
C9 C1 C2 C3 -117.5(2)
C6 C1 C2 C3 10.2(3)
C1 C2 C3 C4 4.0(3)
C2 C3 C4 O2 -175.63(18)
C2 C3 C4 C5 8.3(3)
O2 C4 C5 C6 149.66(18)
C3 C4 C5 C6 -34.3(2)
C4 C5 C6 C7 -70.1(2)
C4 C5 C6 C1 47.6(2)
O1 C1 C6 C7 -25.92(17)
C2 C1 C6 C7 89.61(18)
C9 C1 C6 C7 -143.77(16)
O1 C1 C6 C5 -150.51(14)
C2 C1 C6 C5 -35.0(2)
C9 C1 C6 C5 91.64(19)
C5 C6 C7 C10 -58.1(3)
C1 C6 C7 C10 178.8(2)
C5 C6 C7 C8 124.99(16)
C1 C6 C7 C8 1.91(18)
C1 O1 C8 C7 -40.43(17)
C10 C7 C8 O1 -154.24(18)
C6 C7 C8 O1 22.86(18)
C8 C7 C10 C11 173.7(2)
C6 C7 C10 C11 -2.7(4)
C7 C10 C11 C12 -36.6(4)
C7 C10 C11 C16 146.9(2)
C16 C11 C12 C13 -2.1(3)
C10 C11 C12 C13 -178.65(19)
C11 C12 C13 C14 1.2(3)
C12 C13 C14 C15 0.3(3)
C12 C13 C14 Br1 178.68(14)
C13 C14 C15 C16 -0.7(3)
Br1 C14 C15 C16 -179.07(14)
C12 C11 C16 C15 1.7(3)
C10 C11 C16 C15 178.33(18)
C14 C15 C16 C11 -0.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652133
2 PubChem 139040797
