#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/62/1506206.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_1506206
loop_
_publ_author_name
'Yeager, Adam R.'
'Min, Geanna K.'
'Porco, Jr, John A'
'Schaus, Scott E.'
_publ_section_title
;
 Exploring skeletal diversity via ring contraction of glycal-derived
 scaffolds.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5065
_journal_page_last               5068
_journal_paper_doi               10.1021/ol0618252
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C26 H23 Br O5'
_chemical_formula_weight         495.35
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.015(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.1894(18)
_cell_length_b                   5.1990(10)
_cell_length_c                   17.152(3)
_cell_measurement_reflns_used    2492
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.87
_cell_measurement_theta_min      2.53
_cell_volume                     1105.1(3)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and 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  0.0515
_diffrn_reflns_av_sigmaI/netI    0.0764
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8090
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    1.896
_exptl_absorpt_correction_T_max  0.9631
_exptl_absorpt_correction_T_min  0.2529
_exptl_absorpt_correction_type   'semiempirical by SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             508
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.872
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.021(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0365P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0857
_reflns_number_gt                2590
_reflns_number_total             3034
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0618252si20060724_122752.cif
_cod_data_source_block           porco41
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      P2(1)
_cod_database_code               1506206
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 0.19758(3) 0.06252(11) 0.62419(3) 0.03624(19) Uani 1 1 d .
O1 O -0.1072(3) 1.1408(6) 0.9596(2) 0.0319(10) Uani 1 1 d .
O2 O -0.0656(3) 0.9035(6) 0.7929(2) 0.0273(9) Uani 1 1 d .
O3 O -0.1476(3) 1.0027(7) 0.6580(2) 0.0386(12) Uani 1 1 d .
O4 O -0.2648(3) 0.7511(6) 0.7904(2) 0.0287(9) Uani 1 1 d .
O5 O -0.6583(3) 0.7718(7) 0.5321(2) 0.0344(10) Uani 1 1 d .
C1 C -0.0583(4) 1.2058(12) 0.9005(4) 0.0343(14) Uani 1 1 d .
C2 C -0.1274(4) 1.1035(11) 0.8161(3) 0.0263(13) Uani 1 1 d .
C3 C -0.2228(4) 0.9778(10) 0.8353(3) 0.0249(14) Uani 1 1 d .
C4 C -0.1734(4) 0.9168(11) 0.9272(4) 0.0292(14) Uani 1 1 d .
C5 C -0.0838(4) 0.8770(10) 0.7119(3) 0.0238(12) Uani 1 1 d .
C6 C -0.0166(4) 0.6698(9) 0.6940(3) 0.0227(12) Uani 1 1 d .
C7 C -0.0326(4) 0.6164(10) 0.6122(3) 0.0238(14) Uani 1 1 d .
C8 C 0.0295(4) 0.4299(11) 0.5906(4) 0.0296(13) Uani 1 1 d .
C9 C 0.1094(4) 0.3087(10) 0.6535(3) 0.0264(13) Uani 1 1 d .
C10 C 0.1287(4) 0.3566(11) 0.7363(4) 0.0291(13) Uani 1 1 d .
C11 C 0.0641(3) 0.5411(14) 0.7567(3) 0.0282(11) Uani 1 1 d .
C12 C -0.2502(4) 0.8835(11) 0.9729(3) 0.0282(13) Uani 1 1 d .
C13 C -0.2597(4) 0.6705(12) 1.0117(3) 0.0297(14) Uani 1 1 d .
C14 C -0.3300(4) 0.6256(8) 1.0610(3) 0.0227(13) Uani 1 1 d .
C15 C -0.3120(4) 0.4139(11) 1.1136(4) 0.0305(14) Uani 1 1 d .
C16 C -0.3717(5) 0.3796(13) 1.1661(4) 0.0382(16) Uani 1 1 d .
C17 C -0.4507(4) 0.5549(16) 1.1653(3) 0.0339(12) Uani 1 1 d .
C18 C -0.4705(4) 0.7609(11) 1.1124(4) 0.0319(14) Uani 1 1 d .
C19 C -0.4120(4) 0.7982(11) 1.0598(3) 0.0281(13) Uani 1 1 d .
C20 C -0.3636(4) 0.7744(9) 0.7239(3) 0.0247(12) Uani 1 1 d .
C21 C -0.4409(4) 0.5838(14) 0.7188(3) 0.0295(12) Uani 1 1 d .
C22 C -0.5386(4) 0.5920(14) 0.6545(3) 0.0311(14) Uani 1 1 d .
C23 C -0.5591(4) 0.7839(10) 0.5947(3) 0.0292(13) Uani 1 1 d .
C24 C -0.4830(4) 0.9709(10) 0.5995(4) 0.0317(15) Uani 1 1 d .
C25 C -0.3833(4) 0.9635(10) 0.6652(3) 0.0295(14) Uani 1 1 d .
C26 C -0.6799(4) 0.9614(11) 0.4689(3) 0.0363(15) Uani 1 1 d .
H26A H -0.6837 1.1311 0.4926 0.054 Uiso 1 1 calc R
H26B H -0.7489 0.9232 0.4253 0.054 Uiso 1 1 calc R
H26C H -0.6221 0.9607 0.4451 0.054 Uiso 1 1 calc R
H11 H 0.078(3) 0.542(12) 0.819(3) 0.021(11) Uiso 1 1 d .
H12 H -0.286(4) 1.058(15) 0.978(3) 0.043(13) Uiso 1 1 d .
H17 H -0.495(4) 0.552(15) 1.206(3) 0.054(14) Uiso 1 1 d .
H24 H -0.501(4) 1.122(10) 0.559(3) 0.030(15) Uiso 1 1 d .
H2 H -0.145(3) 1.236(9) 0.774(3) 0.011(12) Uiso 1 1 d .
H8 H 0.018(3) 0.417(8) 0.532(3) 0.017(13) Uiso 1 1 d .
H22 H -0.581(4) 0.469(10) 0.653(3) 0.027(16) Uiso 1 1 d .
H21 H -0.426(4) 0.471(10) 0.758(3) 0.026(16) Uiso 1 1 d .
H10 H 0.186(4) 0.287(10) 0.778(3) 0.036(16) Uiso 1 1 d .
H15 H -0.260(4) 0.295(10) 1.114(3) 0.028(15) Uiso 1 1 d .
H13 H -0.220(3) 0.549(10) 1.013(2) 0.001(11) Uiso 1 1 d .
H7 H -0.099(4) 0.714(10) 0.560(3) 0.042(15) Uiso 1 1 d .
H3 H -0.274(4) 1.089(12) 0.836(3) 0.027(14) Uiso 1 1 d .
H19 H -0.423(4) 0.933(9) 1.021(3) 0.032(15) Uiso 1 1 d .
H4 H -0.132(3) 0.768(9) 0.933(2) 0.003(11) Uiso 1 1 d .
H25 H -0.334(4) 1.090(13) 0.661(3) 0.035(14) Uiso 1 1 d .
H18 H -0.525(4) 0.901(10) 1.111(3) 0.030(14) Uiso 1 1 d .
H1B H 0.010(4) 1.123(9) 0.913(3) 0.024(13) Uiso 1 1 d .
H1A H -0.057(4) 1.402(12) 0.907(3) 0.053(18) Uiso 1 1 d .
H16 H -0.354(4) 0.258(11) 1.202(3) 0.042(18) Uiso 1 1 d .
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
C1 O1 C4 106.2(4)
C5 O2 C2 116.1(4)
C20 O4 C3 116.7(4)
C23 O5 C26 116.9(4)
O1 C1 C2 109.1(4)
O2 C2 C1 107.5(4)
O2 C2 C3 109.1(4)
C1 C2 C3 102.2(4)
O4 C3 C4 109.9(4)
O4 C3 C2 115.5(4)
C4 C3 C2 102.6(4)
O1 C4 C12 108.7(4)
O1 C4 C3 102.6(4)
C12 C4 C3 116.3(4)
O3 C5 O2 124.9(5)
O3 C5 C6 122.7(5)
O2 C5 C6 112.4(4)
C7 C6 C11 120.0(5)
C7 C6 C5 117.5(4)
C11 C6 C5 122.4(5)
C6 C7 C8 120.8(5)
C9 C8 C7 118.1(5)
C8 C9 C10 123.2(5)
C8 C9 Br1 118.2(4)
C10 C9 Br1 118.6(4)
C9 C10 C11 117.8(5)
C6 C11 C10 120.1(5)
C13 C12 C4 124.2(5)
C12 C13 C14 127.5(5)
C15 C14 C19 118.4(5)
C15 C14 C13 119.8(5)
C19 C14 C13 121.7(5)
C14 C15 C16 120.8(6)
C17 C16 C15 120.0(6)
C16 C17 C18 119.6(5)
C17 C18 C19 121.2(5)
C18 C19 C14 120.0(5)
C25 C20 C21 120.7(5)
C25 C20 O4 123.2(5)
C21 C20 O4 116.0(5)
C22 C21 C20 119.2(6)
C21 C22 C23 120.3(6)
C24 C23 O5 123.7(5)
C24 C23 C22 120.5(5)
O5 C23 C22 115.8(5)
C23 C24 C25 119.3(5)
C20 C25 C24 120.0(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C9 1.909(5)
O1 C1 1.417(7)
O1 C4 1.448(6)
O2 C5 1.334(6)
O2 C2 1.457(6)
O3 C5 1.208(6)
O4 C20 1.412(6)
O4 C3 1.413(6)
O5 C23 1.381(6)
O5 C26 1.420(6)
C1 C2 1.519(7)
C2 C3 1.551(7)
C3 C4 1.520(8)
C4 C12 1.488(7)
C5 C6 1.492(7)
C6 C7 1.374(6)
C6 C11 1.398(7)
C7 C8 1.398(7)
C8 C9 1.376(7)
C9 C10 1.377(7)
C10 C11 1.404(8)
C12 C13 1.319(8)
C13 C14 1.472(7)
C14 C15 1.392(7)
C14 C19 1.401(7)
C15 C16 1.395(8)
C16 C17 1.381(9)
C17 C18 1.371(9)
C18 C19 1.386(7)
C20 C25 1.367(7)
C20 C21 1.403(8)
C21 C22 1.381(7)
C22 C23 1.390(8)
C23 C24 1.380(7)
C24 C25 1.409(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21199684
2 PubChem 139039488
