#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/17/4101790.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_4101790
loop_
_publ_author_name
'Sheng Cui'
'Shawn D. Walker'
'Jacqueline C. S. Woo'
'Christopher J. Borths'
'Herschel Mukherjee'
'Maosheng J. Chen'
'Margaret M. Faul'
_publ_section_title
;
 Practical Asymmetric Conjugate Alkynylation of Meldrum's Acid-Derived
 Acceptors: Access to Chiral β-Alkynyl Acids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              436
_journal_page_last               437
_journal_paper_doi               10.1021/ja909105s
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H21 Br O5'
_chemical_formula_sum            'C23 H21 Br O5'
_chemical_formula_weight         457.31
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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                   5.55360(10)
_cell_length_b                   8.6287(2)
_cell_length_c                   42.4623(7)
_cell_measurement_reflns_used    5468
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.32
_cell_measurement_theta_min      4.16
_cell_volume                     2034.81(7)
_computing_cell_refinement       'APEX2 (BRUKER, V5-0, 2008)'
_computing_data_collection       'COSMO (BRUKER, V1.58, 2007)'
_computing_data_reduction        'SAINT (BRUKER, V7.56A, 2008)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_publication_material
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_refinement
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution
'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω,and/f 0.5 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            12637
_diffrn_reflns_theta_full        67.65
_diffrn_reflns_theta_max         67.65
_diffrn_reflns_theta_min         2.08
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.028
_exptl_absorpt_correction_T_max  0.7397
_exptl_absorpt_correction_T_min  0.2063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0495P)²+0.2943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.0996
_reflns_number_gt                3206
_reflns_number_total             3629
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja909105s_si_001.cif
_cod_data_source_block           amg509_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to the built-in table from CIF Core 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_Hall     'P 2ac 2ab '
_cod_database_code               4101790
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
Br1 Br 0.34167(9) 0.36588(7) -0.118061(10) 0.05625(17) Uani 1 1 d . . .
O1 O 0.7791(5) 0.5786(4) 0.01573(6) 0.0437(7) Uani 1 1 d . . .
O2 O 0.7753(4) 0.5036(3) 0.22439(5) 0.0302(5) Uani 1 1 d . . .
O3 O 0.4703(4) 0.3910(3) 0.19355(5) 0.0304(5) Uani 1 1 d . . .
O4 O 0.9907(5) 0.6981(3) 0.20674(6) 0.0427(7) Uani 1 1 d . . .
O5 O 0.3764(5) 0.4849(3) 0.14753(6) 0.0392(6) Uani 1 1 d . . .
C1 C 0.5524(7) 0.3643(5) -0.08228(8) 0.0369(8) Uani 1 1 d . . .
C2 C 0.4921(7) 0.4588(5) -0.05708(9) 0.0353(8) Uani 1 1 d . . .
H2 H 0.3535 0.5232 -0.0579 0.042 Uiso 1 1 calc R . .
C3 C 0.6383(7) 0.4573(4) -0.03055(8) 0.0334(8) Uani 1 1 d . . .
C4 C 0.8418(7) 0.3652(5) -0.03039(9) 0.0414(8) Uani 1 1 d . . .
H4 H 0.9431 0.3638 -0.0124 0.050 Uiso 1 1 calc R . .
C5 C 0.8996(7) 0.2742(5) -0.05646(11) 0.0477(11) Uani 1 1 d . . .
H5 H 1.0407 0.2119 -0.0562 0.057 Uiso 1 1 calc R . .
C6 C 0.7521(8) 0.2744(5) -0.08272(9) 0.0440(10) Uani 1 1 d . . .
H6 H 0.7900 0.2130 -0.1006 0.053 Uiso 1 1 calc R . .
C7 C 0.5703(7) 0.5553(5) -0.00255(9) 0.0404(10) Uani 1 1 d . . .
H7A H 0.5051 0.6561 -0.0097 0.049 Uiso 1 1 calc R . .
H7B H 0.4454 0.5021 0.0101 0.049 Uiso 1 1 calc R . .
C8 C 0.7565(6) 0.6136(5) 0.04739(8) 0.0323(8) Uani 1 1 d . . .
C9 C 0.5639(6) 0.6914(5) 0.06060(8) 0.0344(9) Uani 1 1 d . . .
H9 H 0.4329 0.7241 0.0478 0.041 Uiso 1 1 calc R . .
C10 C 0.5642(6) 0.7214(4) 0.09287(8) 0.0313(8) Uani 1 1 d . . .
H10 H 0.4325 0.7754 0.1020 0.038 Uiso 1 1 calc R . .
C11 C 0.7514(6) 0.6742(4) 0.11161(8) 0.0267(7) Uani 1 1 d . . .
C12 C 0.9438(6) 0.5982(5) 0.09777(9) 0.0355(9) Uani 1 1 d . . .
H12 H 1.0768 0.5673 0.1104 0.043 Uiso 1 1 calc R . .
C13 C 0.9447(7) 0.5667(5) 0.06587(9) 0.0387(9) Uani 1 1 d . . .
H13 H 1.0762 0.5124 0.0568 0.046 Uiso 1 1 calc R . .
C14 C 0.7644(6) 0.7069(4) 0.14715(8) 0.0280(7) Uani 1 1 d . . .
H14 H 0.9234 0.7581 0.1509 0.034 Uiso 1 1 calc R . .
C15 C 0.5816(7) 0.8150(4) 0.15881(8) 0.0292(8) Uani 1 1 d . . .
C16 C 0.4339(7) 0.9016(4) 0.16889(8) 0.0324(8) Uani 1 1 d . . .
C17 C 0.2541(7) 1.0113(5) 0.18077(9) 0.0409(9) Uani 1 1 d . . .
H17A H 0.2701 1.1101 0.1696 0.061 Uiso 1 1 calc R . .
H17B H 0.2796 1.0279 0.2034 0.061 Uiso 1 1 calc R . .
H17C H 0.0924 0.9691 0.1773 0.061 Uiso 1 1 calc R . .
C18 C 0.7641(6) 0.5570(4) 0.16778(8) 0.0282(7) Uani 1 1 d . . .
H18 H 0.8817 0.4835 0.1580 0.034 Uiso 1 1 calc R . .
C19 C 0.5219(6) 0.4768(4) 0.16793(8) 0.0265(7) Uani 1 1 d . . .
C20 C 0.8565(6) 0.5940(4) 0.20074(7) 0.0283(7) Uani 1 1 d . . .
C21 C 0.6475(6) 0.3630(4) 0.21779(7) 0.0286(7) Uani 1 1 d . . .
C22 C 0.8194(7) 0.2378(5) 0.20815(9) 0.0373(8) Uani 1 1 d . . .
H22A H 0.9207 0.2751 0.1908 0.056 Uiso 1 1 calc R . .
H22B H 0.7286 0.1466 0.2012 0.056 Uiso 1 1 calc R . .
H22C H 0.9212 0.2098 0.2261 0.056 Uiso 1 1 calc R . .
C23 C 0.5049(8) 0.3247(5) 0.24700(9) 0.0384(9) Uani 1 1 d . . .
H23A H 0.6155 0.3059 0.2646 0.058 Uiso 1 1 calc R . .
H23B H 0.4080 0.2316 0.2432 0.058 Uiso 1 1 calc R . .
H23C H 0.3985 0.4116 0.2522 0.058 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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C7 119.4(3) . . ?
C20 O2 C21 120.6(3) . . ?
C19 O3 C21 121.5(3) . . ?
C6 C1 C2 123.1(3) . . ?
C6 C1 Br1 119.5(3) . . ?
C2 C1 Br1 117.4(3) . . ?
C1 C2 C3 118.6(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 C7 121.6(3) . . ?
C2 C3 C7 119.2(4) . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C1 C6 C5 118.3(4) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
O1 C7 C3 108.0(3) . . ?
O1 C7 H7A 110.1 . . ?
C3 C7 H7A 110.1 . . ?
O1 C7 H7B 110.1 . . ?
C3 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C13 C8 C9 120.2(3) . . ?
C13 C8 O1 115.0(3) . . ?
C9 C8 O1 124.8(3) . . ?
C8 C9 C10 119.2(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 118.6(3) . . ?
C10 C11 C14 123.4(3) . . ?
C12 C11 C14 117.9(3) . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C8 C13 C12 120.1(3) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C11 114.6(3) . . ?
C15 C14 C18 109.7(3) . . ?
C11 C14 C18 113.5(3) . . ?
C15 C14 H14 106.1 . . ?
C11 C14 H14 106.1 . . ?
C18 C14 H14 106.1 . . ?
C16 C15 C14 178.7(4) . . ?
C15 C16 C17 178.6(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C20 113.0(3) . . ?
C19 C18 C14 112.5(3) . . ?
C20 C18 C14 109.9(3) . . ?
C19 C18 H18 107.0 . . ?
C20 C18 H18 107.0 . . ?
C14 C18 H18 107.0 . . ?
O5 C19 O3 118.5(3) . . ?
O5 C19 C18 125.1(3) . . ?
O3 C19 C18 116.4(3) . . ?
O4 C20 O2 119.0(3) . . ?
O4 C20 C18 124.3(3) . . ?
O2 C20 C18 116.7(3) . . ?
O2 C21 O3 109.6(3) . . ?
O2 C21 C22 110.4(3) . . ?
O3 C21 C22 111.1(3) . . ?
O2 C21 C23 106.6(3) . . ?
O3 C21 C23 105.4(3) . . ?
C22 C21 C23 113.6(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.918(3) . ?
O1 C8 1.384(4) . ?
O1 C7 1.410(4) . ?
O2 C20 1.349(4) . ?
O2 C21 1.433(4) . ?
O3 C19 1.347(4) . ?
O3 C21 1.444(4) . ?
O4 C20 1.195(4) . ?
O5 C19 1.187(4) . ?
C1 C6 1.353(6) . ?
C1 C2 1.386(6) . ?
C2 C3 1.389(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(6) . ?
C3 C7 1.507(5) . ?
C4 C5 1.395(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.368(5) . ?
C8 C9 1.382(5) . ?
C9 C10 1.394(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.371(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(5) . ?
C11 C14 1.537(4) . ?
C12 C13 1.381(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.464(5) . ?
C14 C18 1.562(5) . ?
C14 H14 1.0000 . ?
C15 C16 1.190(5) . ?
C16 C17 1.465(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.512(5) . ?
C18 C20 1.525(4) . ?
C18 H18 1.0000 . ?
C21 C22 1.499(5) . ?
C21 C23 1.509(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -2.3(6) . . . . ?
Br1 C1 C2 C3 178.5(3) . . . . ?
C1 C2 C3 C4 1.6(6) . . . . ?
C1 C2 C3 C7 -177.9(4) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C7 C3 C4 C5 179.3(4) . . . . ?
C3 C4 C5 C6 -0.5(7) . . . . ?
C2 C1 C6 C5 1.6(6) . . . . ?
Br1 C1 C6 C5 -179.3(3) . . . . ?
C4 C5 C6 C1 -0.1(6) . . . . ?
C8 O1 C7 C3 -156.6(3) . . . . ?
C4 C3 C7 O1 21.3(5) . . . . ?
C2 C3 C7 O1 -159.2(3) . . . . ?
C7 O1 C8 C13 151.6(4) . . . . ?
C7 O1 C8 C9 -29.1(6) . . . . ?
C13 C8 C9 C10 0.1(6) . . . . ?
O1 C8 C9 C10 -179.2(4) . . . . ?
C8 C9 C10 C11 -0.4(6) . . . . ?
C9 C10 C11 C12 1.2(6) . . . . ?
C9 C10 C11 C14 178.6(3) . . . . ?
C10 C11 C12 C13 -1.7(6) . . . . ?
C14 C11 C12 C13 -179.3(4) . . . . ?
C9 C8 C13 C12 -0.6(6) . . . . ?
O1 C8 C13 C12 178.7(4) . . . . ?
C11 C12 C13 C8 1.4(6) . . . . ?
C10 C11 C14 C15 -9.8(5) . . . . ?
C12 C11 C14 C15 167.7(3) . . . . ?
C10 C11 C14 C18 117.3(4) . . . . ?
C12 C11 C14 C18 -65.2(4) . . . . ?
C11 C14 C15 C16 160(17) . . . . ?
C18 C14 C15 C16 31(17) . . . . ?
C14 C15 C16 C17 141(17) . . . . ?
C15 C14 C18 C19 58.5(4) . . . . ?
C11 C14 C18 C19 -71.1(4) . . . . ?
C15 C14 C18 C20 -68.5(3) . . . . ?
C11 C14 C18 C20 161.9(3) . . . . ?
C21 O3 C19 O5 173.6(3) . . . . ?
C21 O3 C19 C18 -6.9(4) . . . . ?
C20 C18 C19 O5 151.6(4) . . . . ?
C14 C18 C19 O5 26.3(5) . . . . ?
C20 C18 C19 O3 -27.9(4) . . . . ?
C14 C18 C19 O3 -153.1(3) . . . . ?
C21 O2 C20 O4 -169.6(3) . . . . ?
C21 O2 C20 C18 11.7(4) . . . . ?
C19 C18 C20 O4 -153.0(3) . . . . ?
C14 C18 C20 O4 -26.4(5) . . . . ?
C19 C18 C20 O2 25.7(4) . . . . ?
C14 C18 C20 O2 152.3(3) . . . . ?
C20 O2 C21 O3 -45.3(4) . . . . ?
C20 O2 C21 C22 77.4(4) . . . . ?
C20 O2 C21 C23 -158.8(3) . . . . ?
C19 O3 C21 O2 42.9(4) . . . . ?
C19 O3 C21 C22 -79.3(4) . . . . ?
C19 O3 C21 C23 157.2(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660067
