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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/75/1507527.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_1507527
loop_
_publ_author_name
'Runcie, Karen A.'
'Taylor, Richard J. K.'
_publ_contact_author             'Professor R.J.K. Taylor'
_publ_section_title
;
 A Short and Efficient Route to Novel Scyphostatin Analogues
;
_journal_issue                   21
_journal_name_full               'Organic Letters'
_journal_page_first              3237
_journal_paper_doi               10.1021/ol0164132
_journal_volume                  3
_journal_year                    2001
_chemical_formula_sum            'C11 H15 Br O4'
_chemical_formula_weight         291.14
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 118.02(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.541(3)
_cell_length_b                   8.7123(4)
_cell_length_c                   12.566(3)
_cell_measurement_reflns_used    40
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      10.625
_cell_measurement_theta_min      8.52
_cell_volume                     1212.0(5)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan (MSC,1992-1997)'
_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_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  Rigaku-AFC6S
_diffrn_measurement_method       ω--2θ
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2131
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.98
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.388
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.7967
_exptl_absorpt_correction_type   'semi empirical'
_exptl_absorpt_process_details   psi-scans
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0363P)²+0.4038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0746
_reflns_number_gt                1570
_reflns_number_total             2131
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0164132_s2.cif
_cod_data_source_block           rjkt0112
_cod_original_cell_volume        1212.1(4)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1507527
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1A Br -0.0039(5) 0.8749(7) 0.3645(11) 0.0379(10) Uani 0.69(7) 1 d P A 1
Br1B Br -0.0069(11) 0.8813(13) 0.3523(19) 0.0293(17) Uani 0.31(7) 1 d P A 2
C1 C 0.1542(2) 0.9597(4) 0.4329(3) 0.0214(7) Uani 1 1 d . . .
C2 C 0.2501(3) 0.8535(3) 0.5143(3) 0.0222(6) Uani 1 1 d . A .
H2 H 0.2253 0.7628 0.5433 0.027 Uiso 1 1 calc R . .
O1 O 0.35184(18) 0.8377(2) 0.49005(19) 0.0232(5) Uani 1 1 d . . .
C3 C 0.3681(3) 0.9231(3) 0.5953(3) 0.0198(6) Uani 1 1 d . A .
H3 H 0.4147 0.8708 0.6727 0.024 Uiso 1 1 calc R . .
C4 C 0.3819(2) 1.0961(3) 0.5982(2) 0.0164(6) Uani 1 1 d . . .
C7 C 0.3433(3) 1.1597(3) 0.6887(2) 0.0205(6) Uani 1 1 d . A .
H7A H 0.3614 1.2686 0.6994 0.025 Uiso 1 1 calc R . .
H7B H 0.2565 1.1482 0.6552 0.025 Uiso 1 1 calc R . .
C8 C 0.4037(3) 1.0826(4) 0.8100(3) 0.0252(7) Uani 1 1 d . . .
H8 H 0.4877 1.0839 0.8521 0.030 Uiso 1 1 calc R A .
C9 C 0.3455(3) 1.0135(4) 0.8605(3) 0.0299(7) Uani 1 1 d . A .
H9A H 0.2615 1.0103 0.8209 0.036 Uiso 1 1 calc R . .
H9B H 0.3883 0.9680 0.9359 0.036 Uiso 1 1 calc R . .
O2 O 0.50596(16) 1.1369(2) 0.64473(17) 0.0212(4) Uani 1 1 d . A .
H2A H 0.5313 1.1045 0.5995 0.032 Uiso 1 1 calc R . .
C5 C 0.3021(2) 1.1677(3) 0.4718(3) 0.0178(6) Uani 1 1 d . A .
O3 O 0.36504(16) 1.1394(2) 0.40543(16) 0.0205(4) Uani 1 1 d . . .
C10 C 0.3013(3) 1.1816(4) 0.2803(3) 0.0309(8) Uani 1 1 d . A .
H10A H 0.3504 1.1587 0.2424 0.046 Uiso 1 1 calc R . .
H10B H 0.2838 1.2895 0.2736 0.046 Uiso 1 1 calc R . .
H10C H 0.2272 1.1248 0.2413 0.046 Uiso 1 1 calc R . .
O4 O 0.28062(18) 1.3278(2) 0.47640(19) 0.0225(5) Uani 1 1 d . . .
C11 C 0.3832(3) 1.4274(4) 0.5113(3) 0.0332(8) Uani 1 1 d . A .
H11A H 0.3589 1.5319 0.5112 0.050 Uiso 1 1 calc R . .
H11B H 0.4148 1.4164 0.4553 0.050 Uiso 1 1 calc R . .
H11C H 0.4445 1.4003 0.5908 0.050 Uiso 1 1 calc R . .
C6 C 0.1751(2) 1.1019(3) 0.4116(2) 0.0194(6) Uani 1 1 d . A .
H6 H 0.1110 1.1627 0.3589 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
C6 C1 C2 123.6(3)
C6 C1 Br1A 122.5(4)
C2 C1 Br1A 113.9(3)
C6 C1 Br1B 119.3(5)
C2 C1 Br1B 117.1(5)
Br1A C1 Br1B 4.5(8)
O1 C2 C3 59.20(18)
O1 C2 C1 115.0(2)
C3 C2 C1 116.4(3)
C3 O1 C2 61.27(18)
O1 C3 C2 59.53(18)
O1 C3 C4 120.0(2)
C2 C3 C4 119.4(3)
O2 C4 C3 110.4(2)
O2 C4 C7 105.7(2)
C3 C4 C7 107.8(2)
O2 C4 C5 111.9(2)
C3 C4 C5 111.3(2)
C7 C4 C5 109.7(2)
C8 C7 C4 113.9(2)
C9 C8 C7 124.2(3)
O3 C5 O4 111.3(2)
O3 C5 C6 112.7(2)
O4 C5 C6 102.4(2)
O3 C5 C4 105.3(2)
O4 C5 C4 113.2(2)
C6 C5 C4 112.2(2)
C5 O3 C10 115.1(2)
C5 O4 C11 116.3(2)
C1 C6 C5 121.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1A C1 1.901(7)
Br1B C1 1.911(13)
C1 C6 1.319(4)
C1 C2 1.481(4)
C2 O1 1.451(3)
C2 C3 1.477(4)
O1 C3 1.446(4)
C3 C4 1.515(4)
C4 O2 1.426(3)
C4 C7 1.534(4)
C4 C5 1.556(4)
C7 C8 1.505(4)
C8 C9 1.317(4)
C5 O3 1.413(3)
C5 O4 1.427(3)
C5 C6 1.519(4)
O3 C10 1.437(3)
O4 C11 1.439(4)
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
C6 C1 C2 O1 -52.0(4)
Br1A C1 C2 O1 129.8(4)
Br1B C1 C2 O1 126.3(7)
C6 C1 C2 C3 14.5(4)
Br1A C1 C2 C3 -163.7(4)
Br1B C1 C2 C3 -167.2(7)
C1 C2 O1 C3 107.1(3)
C2 O1 C3 C4 -108.6(3)
C1 C2 C3 O1 -104.7(3)
O1 C2 C3 C4 109.5(3)
C1 C2 C3 C4 4.8(4)
O1 C3 C4 O2 -89.1(3)
C2 C3 C4 O2 -158.8(2)
O1 C3 C4 C7 156.0(2)
C2 C3 C4 C7 86.3(3)
O1 C3 C4 C5 35.7(3)
C2 C3 C4 C5 -34.0(4)
O2 C4 C7 C8 -66.8(3)
C3 C4 C7 C8 51.2(3)
C5 C4 C7 C8 172.5(2)
C4 C7 C8 C9 -122.3(3)
O2 C4 C5 O3 46.5(3)
C3 C4 C5 O3 -77.5(3)
C7 C4 C5 O3 163.4(2)
O2 C4 C5 O4 -75.3(3)
C3 C4 C5 O4 160.7(2)
C7 C4 C5 O4 41.6(3)
O2 C4 C5 C6 169.4(2)
C3 C4 C5 C6 45.4(3)
C7 C4 C5 C6 -73.7(3)
O4 C5 O3 C10 -63.4(3)
C6 C5 O3 C10 51.0(3)
C4 C5 O3 C10 173.6(2)
O3 C5 O4 C11 -49.5(3)
C6 C5 O4 C11 -170.2(2)
C4 C5 O4 C11 68.8(3)
C2 C1 C6 C5 -0.5(4)
Br1A C1 C6 C5 177.5(4)
Br1B C1 C6 C5 -178.8(7)
O3 C5 C6 C1 88.2(3)
O4 C5 C6 C1 -152.1(3)
C4 C5 C6 C1 -30.4(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139040106
