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#$Date: 2025-08-20 17:59:05 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301833 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/20/4112041.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_4112041
loop_
_publ_author_name
'Michael A. Calter'
'Ryan M. Phillips'
'Christine Flaschenriem'
_publ_section_title
;
 Catalytic, Asymmetric, "Interrupted" Feist-Bénary Reactions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14566
_journal_page_last               14567
_journal_paper_doi               10.1021/ja055752d
_journal_volume                  127
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H17 Br O5'
_chemical_formula_sum            'C17 H17 Br O5'
_chemical_formula_weight         381.22
_chemical_name_common            CALRP04
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 106.2290(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3924(4)
_cell_length_b                   9.3336(5)
_cell_length_c                   11.8117(7)
_cell_measurement_reflns_used    6629
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.70
_cell_measurement_theta_min      2.83
_cell_volume                     782.51(8)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12005
_diffrn_reflns_theta_full        31.12
_diffrn_reflns_theta_max         31.12
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    2.650
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_meas      0
_exptl_crystal_description       Needle
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4644
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0234
_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)+(0.0391P)²+0.0761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0588
_refine_ls_wR_factor_ref         0.0678
_reflns_number_gt                4342
_reflns_number_total             4644
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja055752dsi20050815_031952.cif
_cod_data_source_block           asd
_cod_database_code               4112041
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 0.95207(2) 0.35706(2) -0.008018(14) 0.02386(6) Uani 1 1 d .
O2 O 0.92423(17) 0.3627(2) 0.72678(11) 0.0235(3) Uani 1 1 d .
O3 O 0.45895(19) 0.45855(17) 0.55229(13) 0.0205(3) Uani 1 1 d .
H3 H 0.4997 0.5042 0.5032 0.031 Uiso 1 1 calc R
O4 O 0.5233(2) 0.55570(16) 0.82298(14) 0.0190(3) Uani 1 1 d .
O1 O 0.80587(19) 0.40335(15) 0.53349(12) 0.0175(3) Uani 1 1 d .
O5 O 0.5481(2) 0.12342(17) 0.64022(14) 0.0243(3) Uani 1 1 d .
C14 C 0.3310(3) 0.2031(2) 0.87536(19) 0.0197(4) Uani 1 1 d .
H14A H 0.3124 0.1513 0.9444 0.024 Uiso 1 1 calc R
H14B H 0.2059 0.2153 0.8177 0.024 Uiso 1 1 calc R
C4 C 0.9766(2) 0.3625(3) 0.39112(14) 0.0164(3) Uani 1 1 d .
C1 C 0.9610(2) 0.3596(3) 0.15442(13) 0.0179(3) Uani 1 1 d .
C15 C 0.4550(3) 0.1126(2) 0.8195(2) 0.0210(4) Uani 1 1 d .
H15A H 0.5697 0.0842 0.8816 0.025 Uiso 1 1 calc R
H15B H 0.3860 0.0241 0.7872 0.025 Uiso 1 1 calc R
C17 C 0.5356(2) 0.3416(2) 0.73535(14) 0.0138(3) Uani 1 1 d .
C13 C 0.4141(2) 0.3507(3) 0.91490(14) 0.0181(3) Uani 1 1 d .
H13A H 0.3152 0.4140 0.9290 0.022 Uiso 1 1 calc R
H13B H 0.5158 0.3418 0.9896 0.022 Uiso 1 1 calc R
C16 C 0.5132(3) 0.1886(2) 0.72189(17) 0.0161(3) Uani 1 1 d .
C10 C 0.6356(3) 0.5808(2) 0.73930(19) 0.0177(4) Uani 1 1 d .
H10 H 0.7718 0.5849 0.7846 0.021 Uiso 1 1 calc R
C3 C 1.0524(3) 0.4753(2) 0.34226(17) 0.0164(3) Uani 1 1 d .
H3A H 1.1105 0.5532 0.3907 0.020 Uiso 1 1 calc R
C12 C 0.4907(3) 0.4141(2) 0.82274(16) 0.0141(3) Uani 1 1 d .
C8 C 0.7943(3) 0.39718(19) 0.64440(16) 0.0158(3) Uani 1 1 d .
C9 C 0.6027(3) 0.4447(2) 0.65806(17) 0.0146(3) Uani 1 1 d .
C6 C 0.8856(3) 0.2456(2) 0.20082(19) 0.0207(4) Uani 1 1 d .
H6 H 0.8287 0.1675 0.1522 0.025 Uiso 1 1 calc R
C11 C 0.5818(3) 0.7208(2) 0.6764(2) 0.0270(5) Uani 1 1 d .
H11A H 0.4500 0.7168 0.6288 0.040 Uiso 1 1 calc R
H11B H 0.6628 0.7388 0.6249 0.040 Uiso 1 1 calc R
H11C H 0.5976 0.7983 0.7343 0.040 Uiso 1 1 calc R
C7 C 0.9897(2) 0.3616(3) 0.52009(15) 0.0183(3) Uani 1 1 d .
H7A H 1.0240 0.2647 0.5532 0.022 Uiso 1 1 calc R
H7B H 1.0877 0.4298 0.5627 0.022 Uiso 1 1 calc R
C2 C 1.0441(3) 0.4750(2) 0.22319(17) 0.0178(3) Uani 1 1 d .
H2 H 1.0944 0.5526 0.1896 0.021 Uiso 1 1 calc R
C5 C 0.8948(3) 0.2475(2) 0.31982(18) 0.0196(4) Uani 1 1 d .
H5 H 0.8447 0.1695 0.3531 0.024 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
C12 O4 C10 106.76(15)
C8 O1 C7 114.18(14)
C15 C14 C13 113.11(16)
C3 C4 C5 119.29(16)
C3 C4 C7 120.4(2)
C5 C4 C7 120.2(2)
C6 C1 C2 121.84(16)
C6 C1 Br1 119.07(18)
C2 C1 Br1 119.08(17)
C16 C15 C14 113.78(16)
C12 C17 C16 122.38(17)
C12 C17 C9 109.70(18)
C16 C17 C9 127.89(16)
C12 C13 C14 109.82(15)
O5 C16 C17 122.34(18)
O5 C16 C15 122.23(18)
C17 C16 C15 115.33(17)
O4 C10 C11 110.41(16)
O4 C10 C9 105.13(14)
C11 C10 C9 115.32(18)
C2 C3 C4 120.58(18)
O4 C12 C17 114.36(17)
O4 C12 C13 119.74(17)
C17 C12 C13 125.90(19)
O2 C8 O1 123.23(17)
O2 C8 C9 122.89(16)
O1 C8 C9 113.82(16)
O3 C9 C17 107.68(14)
O3 C9 C8 115.16(15)
C17 C9 C8 110.51(15)
O3 C9 C10 114.79(15)
C17 C9 C10 99.64(15)
C8 C9 C10 107.94(15)
C1 C6 C5 118.68(19)
O1 C7 C4 108.08(14)
C1 C2 C3 118.81(18)
C6 C5 C4 120.79(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.9014(15)
O2 C8 1.204(2)
O3 C9 1.402(2)
O4 C12 1.343(2)
O4 C10 1.477(2)
O1 C8 1.338(2)
O1 C7 1.464(2)
O5 C16 1.227(2)
C14 C15 1.525(3)
C14 C13 1.528(3)
C4 C3 1.392(3)
C4 C5 1.394(3)
C4 C7 1.499(2)
C1 C6 1.384(3)
C1 C2 1.385(3)
C15 C16 1.515(3)
C17 C12 1.351(3)
C17 C16 1.442(3)
C17 C9 1.503(3)
C13 C12 1.484(3)
C10 C11 1.501(3)
C10 C9 1.570(3)
C3 C2 1.390(3)
C8 C9 1.535(3)
C6 C5 1.388(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139118887
