#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/46/1504605.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_1504605
loop_
_publ_author_name
'Adams, Harry'
'Gilmore, Nathan J.'
'Jones, Simon'
'Muldowney, Mark P.'
'von Reuss, Stephan H.'
'Vemula, Ramesh'
_publ_section_title
;
 Asymmetric synthesis of corsifuran A by an enantioselective
 oxazaborolidine reduction.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1457
_journal_page_last               1460
_journal_paper_doi               10.1021/ol800239q
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H17 Br O3'
_chemical_formula_sum            'C16 H17 Br O3'
_chemical_formula_weight         337.21
_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                   4.656(2)
_cell_length_b                   13.095(6)
_cell_length_c                   23.986(11)
_cell_measurement_reflns_used    5019
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      53.245
_cell_measurement_theta_min      4.605
_cell_volume                     1462.4(11)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      150(2)
_diffrn_detector_area_resol_mean 100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART1000'
_diffrn_measurement_method       '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  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            15086
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.70
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.815
_exptl_absorpt_correction_T_max  0.8957
_exptl_absorpt_correction_T_min  0.3513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0311
_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)+(0.0234P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0651
_reflns_number_gt                2865
_reflns_number_total             3304
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800239q-file004.cif
_cod_data_source_block           osj39m
_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 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1462.5(11)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1504605
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 -0.28213(6) -0.09967(2) 0.122219(11) 0.03319(9) Uani 1 1 d .
O1 O -0.1078(4) -0.07560(13) -0.12628(8) 0.0352(5) Uani 1 1 d .
O2 O -0.1054(4) 0.22008(13) 0.02775(7) 0.0242(4) Uani 1 1 d .
H2 H 0.0508 0.2355 0.0124 0.036 Uiso 1 1 calc R
O3 O 0.5376(5) 0.33459(15) 0.25734(8) 0.0373(5) Uani 1 1 d .
C1 C -0.2380(5) -0.08372(17) 0.04328(10) 0.0245(5) Uani 1 1 d .
C2 C -0.4022(6) -0.1471(2) 0.01039(12) 0.0275(6) Uani 1 1 d .
H2A H -0.5373 -0.1921 0.0270 0.033 Uiso 1 1 calc R
C3 C -0.3697(6) -0.14504(19) -0.04716(12) 0.0296(7) Uani 1 1 d .
H3 H -0.4835 -0.1879 -0.0702 0.036 Uiso 1 1 calc R
C4 C -0.1700(6) -0.07986(18) -0.07036(11) 0.0258(6) Uani 1 1 d .
C5 C -0.0129(6) -0.0143(2) -0.03668(11) 0.0255(6) Uani 1 1 d .
H5 H 0.1201 0.0314 -0.0534 0.031 Uiso 1 1 calc R
C6 C -0.0452(6) -0.01382(19) 0.02098(11) 0.0226(6) Uani 1 1 d .
C7 C 0.1225(6) 0.06005(18) 0.05657(11) 0.0237(6) Uani 1 1 d .
H7A H 0.2941 0.0827 0.0356 0.028 Uiso 1 1 calc R
H7B H 0.1899 0.0240 0.0904 0.028 Uiso 1 1 calc R
C8 C -0.0510(5) 0.15468(18) 0.07436(10) 0.0213(6) Uani 1 1 d .
H8 H -0.2406 0.1304 0.0887 0.026 Uiso 1 1 calc R
C9 C 0.1020(5) 0.20869(17) 0.12185(11) 0.0218(5) Uani 1 1 d .
C10 C 0.0785(7) 0.1701(2) 0.17578(12) 0.0324(7) Uani 1 1 d .
H10 H -0.0437 0.1134 0.1826 0.039 Uiso 1 1 calc R
C11 C 0.2289(7) 0.2126(2) 0.21953(11) 0.0343(7) Uani 1 1 d .
H11 H 0.2132 0.1840 0.2558 0.041 Uiso 1 1 calc R
C12 C 0.4016(6) 0.2963(2) 0.21093(11) 0.0274(6) Uani 1 1 d .
C13 C 0.4274(6) 0.3361(2) 0.15810(11) 0.0287(6) Uani 1 1 d .
H13 H 0.5488 0.3932 0.1515 0.034 Uiso 1 1 calc R
C14 C 0.2757(6) 0.29265(18) 0.11454(11) 0.0290(6) Uani 1 1 d .
H14 H 0.2920 0.3217 0.0784 0.035 Uiso 1 1 calc R
C15 C 0.7204(7) 0.4206(2) 0.24992(12) 0.0396(7) Uani 1 1 d .
H15A H 0.6079 0.4782 0.2357 0.059 Uiso 1 1 calc R
H15B H 0.8722 0.4036 0.2232 0.059 Uiso 1 1 calc R
H15C H 0.8071 0.4392 0.2857 0.059 Uiso 1 1 calc R
C16 C -0.2909(7) -0.1331(2) -0.16210(12) 0.0456(8) Uani 1 1 d .
H16A H -0.4911 -0.1132 -0.1557 0.068 Uiso 1 1 calc R
H16B H -0.2678 -0.2061 -0.1542 0.068 Uiso 1 1 calc R
H16C H -0.2398 -0.1196 -0.2010 0.068 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
C4 O1 C16 116.2(2)
C8 O2 H2 109.5
C12 O3 C15 117.5(2)
C2 C1 C6 122.4(2)
C2 C1 Br1 116.2(2)
C6 C1 Br1 121.44(19)
C1 C2 C3 119.8(3)
C1 C2 H2A 120.1
C3 C2 H2A 120.1
C4 C3 C2 119.1(3)
C4 C3 H3 120.5
C2 C3 H3 120.5
O1 C4 C3 124.1(2)
O1 C4 C5 115.6(2)
C3 C4 C5 120.2(3)
C4 C5 C6 121.6(2)
C4 C5 H5 119.2
C6 C5 H5 119.2
C1 C6 C5 116.7(2)
C1 C6 C7 122.6(2)
C5 C6 C7 120.6(2)
C6 C7 C8 113.7(2)
C6 C7 H7A 108.8
C8 C7 H7A 108.8
C6 C7 H7B 108.8
C8 C7 H7B 108.8
H7A C7 H7B 107.7
O2 C8 C9 113.0(2)
O2 C8 C7 111.0(2)
C9 C8 C7 109.7(2)
O2 C8 H8 107.7
C9 C8 H8 107.7
C7 C8 H8 107.7
C14 C9 C10 117.0(2)
C14 C9 C8 123.5(2)
C10 C9 C8 119.4(2)
C11 C10 C9 121.3(3)
C11 C10 H10 119.3
C9 C10 H10 119.3
C12 C11 C10 120.3(3)
C12 C11 H11 119.8
C10 C11 H11 119.8
O3 C12 C11 116.0(2)
O3 C12 C13 124.6(3)
C11 C12 C13 119.4(3)
C12 C13 C14 119.7(3)
C12 C13 H13 120.2
C14 C13 H13 120.2
C9 C14 C13 122.2(2)
C9 C14 H14 118.9
C13 C14 H14 118.9
O3 C15 H15A 109.5
O3 C15 H15B 109.5
H15A C15 H15B 109.5
O3 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
O1 C16 H16A 109.5
O1 C16 H16B 109.5
H16A C16 H16B 109.5
O1 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.916(3)
O1 C4 1.373(3)
O1 C16 1.426(3)
O2 C8 1.431(3)
O2 H2 0.8400
O3 C12 1.375(3)
O3 C15 1.423(3)
C1 C2 1.376(4)
C1 C6 1.389(4)
C2 C3 1.389(4)
C2 H2A 0.9500
C3 C4 1.379(4)
C3 H3 0.9500
C4 C5 1.387(4)
C5 C6 1.391(4)
C5 H5 0.9500
C6 C7 1.508(3)
C7 C8 1.540(3)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.518(4)
C8 H8 1.0000
C9 C14 1.376(3)
C9 C10 1.393(4)
C10 C11 1.379(4)
C10 H10 0.9500
C11 C12 1.375(4)
C11 H11 0.9500
C12 C13 1.375(4)
C13 C14 1.384(3)
C13 H13 0.9500
C14 H14 0.9500
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
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 O2 0.84 1.96 2.794(2) 174.8 4
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139038662
