#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:18:58 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178808 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/62/4106260.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_4106260
loop_
_publ_author_name
'Scott A. Snyder'
'Daniel A. Wespe'
'J. Marian von Hof'
_publ_section_title
;
 A Concise, Stereocontrolled Total Synthesis of Rippertenol
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8850
_journal_page_last               8853
_journal_paper_doi               10.1021/ja202859f
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C22 H25 Br O4'
_chemical_formula_weight         433.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 93.219(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.341(4)
_cell_length_b                   7.8924(15)
_cell_length_c                   11.615(2)
_cell_measurement_reflns_used    5948
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      28.75
_cell_measurement_theta_min      2.75
_cell_volume                     1953.2(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.1122
_diffrn_reflns_av_sigmaI/netI    0.0912
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27300
_diffrn_reflns_theta_full        29.13
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    2.130
_exptl_absorpt_correction_T_max  0.9197
_exptl_absorpt_correction_T_min  0.5771
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.384
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         5246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1301
_refine_ls_R_factor_gt           0.0708
_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)+(0.0920P)²+6.0147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1731
_refine_ls_wR_factor_ref         0.2027
_reflns_number_gt                3211
_reflns_number_total             5246
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja202859f_si_002.cif
_cod_data_source_block           dws10
_cod_original_cell_volume        1953.2(7)
_cod_database_code               4106260
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br Br 0.41315(3) -0.95930(8) -0.23287(5) 0.03174(19) Uani 1 1 d .
O1 O 0.93364(17) -0.1723(4) 0.2405(3) 0.0240(8) Uani 1 1 d .
O2 O 0.90029(15) -0.5386(4) -0.0793(3) 0.0175(7) Uani 1 1 d .
H2A H 0.9083 -0.4582 -0.1235 0.026 Uiso 1 1 calc R
O3 O 0.69665(16) -0.6987(4) 0.0012(3) 0.0209(7) Uani 1 1 d .
O4 O 0.63503(17) -0.5781(5) 0.1305(3) 0.0304(9) Uani 1 1 d .
C1 C 0.9371(2) -0.3661(6) 0.0824(4) 0.0153(9) Uani 1 1 d .
H1A H 0.9764 -0.4316 0.0775 0.018 Uiso 1 1 calc R
H1B H 0.9411 -0.2612 0.0366 0.018 Uiso 1 1 calc R
C2 C 0.9291(2) -0.3190(6) 0.2064(4) 0.0189(10) Uani 1 1 d .
C3 C 0.9152(2) -0.4660(7) 0.2841(4) 0.0232(10) Uani 1 1 d .
H3A H 0.9052 -0.4233 0.3610 0.028 Uiso 1 1 calc R
H3B H 0.9526 -0.5401 0.2937 0.028 Uiso 1 1 calc R
C4 C 0.8595(2) -0.5679(6) 0.2312(4) 0.0181(10) Uani 1 1 d .
H4A H 0.8212 -0.4971 0.2321 0.022 Uiso 1 1 calc R
H4B H 0.8529 -0.6683 0.2802 0.022 Uiso 1 1 calc R
C5 C 0.8678(2) -0.6283(6) 0.1055(4) 0.0166(9) Uani 1 1 d .
C6 C 0.8818(2) -0.4718(6) 0.0293(4) 0.0143(9) Uani 1 1 d .
C7 C 0.8229(2) -0.3638(6) 0.0093(4) 0.0153(9) Uani 1 1 d .
C8 C 0.8166(2) -0.1977(6) 0.0215(5) 0.0222(11) Uani 1 1 d .
H8A H 0.8500 -0.1251 0.0476 0.027 Uiso 1 1 calc R
C9 C 0.7509(2) -0.1360(7) -0.0105(5) 0.0259(11) Uani 1 1 d .
H9A H 0.7486 -0.0802 -0.0869 0.031 Uiso 1 1 calc R
H9B H 0.7362 -0.0561 0.0479 0.031 Uiso 1 1 calc R
C10 C 0.7129(2) -0.3011(6) -0.0126(5) 0.0266(12) Uani 1 1 d .
H10A H 0.6796 -0.2985 -0.0756 0.032 Uiso 1 1 calc R
H10B H 0.6929 -0.3175 0.0615 0.032 Uiso 1 1 calc R
C11 C 0.7606(2) -0.4465(6) -0.0328(4) 0.0185(10) Uani 1 1 d .
C12 C 0.7505(2) -0.5987(6) 0.0469(4) 0.0188(10) Uani 1 1 d .
H12A H 0.7415 -0.5558 0.1253 0.023 Uiso 1 1 calc R
C13 C 0.8072(2) -0.7167(6) 0.0575(4) 0.0185(10) Uani 1 1 d .
H13A H 0.8146 -0.7642 -0.0195 0.022 Uiso 1 1 calc R
H13B H 0.7976 -0.8123 0.1088 0.022 Uiso 1 1 calc R
C14 C 0.9211(2) -0.7582(6) 0.1043(5) 0.0231(11) Uani 1 1 d .
H14A H 0.9224 -0.8072 0.0270 0.035 Uiso 1 1 calc R
H14B H 0.9137 -0.8483 0.1600 0.035 Uiso 1 1 calc R
H14C H 0.9611 -0.7023 0.1251 0.035 Uiso 1 1 calc R
C15 C 0.7599(3) -0.4954(7) -0.1599(4) 0.0244(11) Uani 1 1 d .
H15A H 0.7918 -0.5822 -0.1709 0.037 Uiso 1 1 calc R
H15B H 0.7689 -0.3952 -0.2060 0.037 Uiso 1 1 calc R
H15C H 0.7184 -0.5401 -0.1846 0.037 Uiso 1 1 calc R
C16 C 0.6409(2) -0.6682(6) 0.0483(4) 0.0209(10) Uani 1 1 d .
C17 C 0.5874(2) -0.7521(6) -0.0173(4) 0.0180(9) Uani 1 1 d .
C18 C 0.5271(2) -0.7077(6) 0.0121(4) 0.0214(10) Uani 1 1 d .
H18A H 0.5216 -0.6347 0.0758 0.026 Uiso 1 1 calc R
C19 C 0.4748(2) -0.7700(7) -0.0516(4) 0.0235(11) Uani 1 1 d .
H19A H 0.4336 -0.7383 -0.0332 0.028 Uiso 1 1 calc R
C20 C 0.4843(2) -0.8798(6) -0.1426(4) 0.0203(10) Uani 1 1 d .
C21 C 0.5434(2) -0.9324(6) -0.1699(4) 0.0221(10) Uani 1 1 d .
H21A H 0.5485 -1.0121 -0.2299 0.026 Uiso 1 1 calc R
C22 C 0.5956(2) -0.8655(6) -0.1072(4) 0.0195(10) Uani 1 1 d .
H22A H 0.6367 -0.8975 -0.1259 0.023 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
C16 O3 C12 116.4(4)
C2 C1 C6 113.0(4)
O1 C2 C1 122.0(5)
O1 C2 C3 123.2(5)
C1 C2 C3 114.7(4)
C2 C3 C4 109.8(4)
C3 C4 C5 114.1(4)
C14 C5 C13 107.5(4)
C14 C5 C4 109.8(4)
C13 C5 C4 109.8(4)
C14 C5 C6 111.1(4)
C13 C5 C6 109.6(4)
C4 C5 C6 109.0(4)
O2 C6 C7 109.6(4)
O2 C6 C1 107.8(4)
C7 C6 C1 111.3(4)
O2 C6 C5 106.1(4)
C7 C6 C5 110.3(4)
C1 C6 C5 111.6(4)
C8 C7 C6 128.5(4)
C8 C7 C11 111.3(4)
C6 C7 C11 120.1(4)
C7 C8 C9 113.0(4)
C8 C9 C10 102.3(4)
C9 C10 C11 106.1(4)
C15 C11 C7 112.1(4)
C15 C11 C12 113.0(4)
C7 C11 C12 106.7(4)
C15 C11 C10 111.1(4)
C7 C11 C10 101.5(4)
C12 C11 C10 111.7(4)
O3 C12 C13 107.5(4)
O3 C12 C11 109.6(4)
C13 C12 C11 112.9(4)
C12 C13 C5 113.4(4)
O4 C16 O3 123.8(4)
O4 C16 C17 123.8(5)
O3 C16 C17 112.3(4)
C22 C17 C18 120.1(4)
C22 C17 C16 122.9(5)
C18 C17 C16 117.0(5)
C19 C18 C17 120.2(5)
C20 C19 C18 118.5(5)
C21 C20 C19 122.4(4)
C21 C20 Br 119.0(4)
C19 C20 Br 118.6(4)
C20 C21 C22 118.5(5)
C17 C22 C21 120.1(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C20 1.903(5)
O1 C2 1.226(6)
O2 C6 1.443(5)
O3 C16 1.358(6)
O3 C12 1.469(5)
O4 C16 1.203(6)
C1 C2 1.506(7)
C1 C6 1.545(6)
C2 C3 1.509(7)
C3 C4 1.535(7)
C4 C5 1.555(7)
C5 C14 1.531(7)
C5 C13 1.547(6)
C5 C6 1.558(7)
C6 C7 1.526(6)
C7 C8 1.326(7)
C7 C11 1.536(6)
C8 C9 1.511(7)
C9 C10 1.535(7)
C10 C11 1.561(7)
C11 C15 1.526(7)
C11 C12 1.539(7)
C12 C13 1.526(7)
C16 C17 1.492(7)
C17 C22 1.394(7)
C17 C18 1.395(7)
C18 C19 1.393(7)
C19 C20 1.390(7)
C20 C21 1.381(7)
C21 C22 1.400(7)
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 H2A O1 0.84 1.99 2.798(5) 162.1 4
