#------------------------------------------------------------------------------
#$Date: 2019-07-09 11:38:00 +0300 (Tue, 09 Jul 2019) $
#$Revision: 216883 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/20/1552065.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_1552065
loop_
_publ_author_name
'Gang Liu'
'Morgan E. Shirley'
'Khoi N. Van'
'Rae Lynn McFarlin'
'Daniel Romo'
_publ_section_title
;
 Rapid assembly of complex cyclopentanes employing chiral,
 alpha,beta-unsaturated acylammonium intermediates
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              1049
_journal_page_last               1057
_journal_paper_doi               10.1038/nchem.1788
_journal_volume                  5
_journal_year                    2013
_chemical_formula_sum            'C12 H16 O6'
_chemical_formula_weight         256.25
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                102.611(7)
_cell_angle_beta                 90.215(7)
_cell_angle_gamma                106.979(7)
_cell_formula_units_Z            2
_cell_length_a                   6.891(4)
_cell_length_b                   9.592(6)
_cell_length_c                   10.273(7)
_cell_measurement_reflns_used    1001
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.62
_cell_measurement_theta_min      2.69
_cell_volume                     632.1(7)
_computing_cell_refinement
; 
  APEX-II(BRUKER-NONIUS, 2003) 
;
_computing_data_collection       'APEX-II (BRUKER-NONIUS, 2003)'
_computing_data_reduction        APEX-II
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'APEX II'
_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  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7210
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.69
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_correction_T_min  0.9397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0371
_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)+(0.0463P)²+0.1226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                2434
_reflns_number_total             2858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            nchem.1788-s3.cif
_cod_data_source_block           drb
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1552065
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.90810(18) 0.09861(13) 0.68328(12) 0.0233(2) Uani 1 1 d . . .
H1A H 1.0128 0.0485 0.6504 0.028 Uiso 1 1 calc R . .
C2 C 0.98254(17) 0.26775(12) 0.67760(11) 0.0203(2) Uani 1 1 d . . .
C3 C 0.87762(18) 0.34558(13) 0.79127(11) 0.0240(2) Uani 1 1 d . . .
H3A H 0.9597 0.4513 0.8259 0.029 Uiso 1 1 calc R . .
H3B H 0.7410 0.3432 0.7587 0.029 Uiso 1 1 calc R . .
C4 C 0.86101(18) 0.25864(15) 0.89937(12) 0.0276(3) Uani 1 1 d . . .
C5 C 0.88436(18) 0.10417(14) 0.83332(12) 0.0271(3) Uani 1 1 d . . .
H5A H 0.7770 0.0170 0.8529 0.033 Uiso 1 1 calc R . .
C6 C 0.70326(19) 0.01466(14) 0.60502(13) 0.0307(3) Uani 1 1 d . . .
H6A H 0.6583 -0.0881 0.6174 0.046 Uiso 1 1 calc R . .
H6B H 0.7175 0.0126 0.5098 0.046 Uiso 1 1 calc R . .
H6C H 0.6026 0.0656 0.6376 0.046 Uiso 1 1 calc R . .
C7 C 0.6997(2) 0.27079(19) 0.99492(14) 0.0406(4) Uani 1 1 d . . .
H7A H 0.7238 0.3759 1.0407 0.061 Uiso 1 1 calc R . .
H7B H 0.7041 0.2118 1.0611 0.061 Uiso 1 1 calc R . .
H7C H 0.5659 0.2326 0.9455 0.061 Uiso 1 1 calc R . .
C8 C 1.07842(19) 0.15574(15) 0.92413(13) 0.0311(3) Uani 1 1 d . . .
C9 C 1.21490(17) 0.32974(13) 0.69731(11) 0.0215(2) Uani 1 1 d . . .
C10 C 1.4893(2) 0.54762(15) 0.70176(16) 0.0357(3) Uani 1 1 d . . .
H10A H 1.5144 0.6463 0.6814 0.054 Uiso 1 1 calc R . .
H10B H 1.5532 0.4866 0.6372 0.054 Uiso 1 1 calc R . .
H10C H 1.5471 0.5596 0.7923 0.054 Uiso 1 1 calc R . .
C11 C 0.91862(18) 0.28913(13) 0.54197(12) 0.0237(2) Uani 1 1 d . . .
C12 C 0.9766(2) 0.24876(16) 0.31252(12) 0.0348(3) Uani 1 1 d . . .
H12A H 1.0767 0.2228 0.2519 0.052 Uiso 1 1 calc R . .
H12B H 0.9754 0.3509 0.3135 0.052 Uiso 1 1 calc R . .
H12C H 0.8414 0.1786 0.2817 0.052 Uiso 1 1 calc R . .
O1 O 1.06532(13) 0.29653(11) 0.97597(9) 0.0334(2) Uani 1 1 d . . .
O2 O 1.20540(14) 0.10441(12) 0.95395(11) 0.0415(3) Uani 1 1 d . . .
O3 O 1.32922(13) 0.26003(9) 0.71257(9) 0.0291(2) Uani 1 1 d . . .
O4 O 1.27258(13) 0.47450(9) 0.69355(9) 0.0282(2) Uani 1 1 d . . .
O5 O 0.78493(15) 0.33976(12) 0.52232(9) 0.0388(3) Uani 1 1 d . . .
O6 O 1.03075(13) 0.23991(9) 0.44654(8) 0.0268(2) Uani 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'
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
C6 C1 C5 109.34(10) . .
C6 C1 C2 112.57(9) . .
C5 C1 C2 103.56(9) . .
C6 C1 H1A 110.4 . .
C5 C1 H1A 110.4 . .
C2 C1 H1A 110.4 . .
C9 C2 C11 107.45(9) . .
C9 C2 C3 112.15(9) . .
C11 C2 C3 110.86(10) . .
C9 C2 C1 111.06(9) . .
C11 C2 C1 111.11(9) . .
C3 C2 C1 104.27(10) . .
C4 C3 C2 105.91(10) . .
C4 C3 H3A 110.6 . .
C2 C3 H3A 110.6 . .
C4 C3 H3B 110.6 . .
C2 C3 H3B 110.6 . .
H3A C3 H3B 108.7 . .
C7 C4 C3 116.40(11) . .
C7 C4 O1 110.06(11) . .
C3 C4 O1 110.77(10) . .
C7 C4 C5 120.45(12) . .
C3 C4 C5 107.13(10) . .
O1 C4 C5 88.59(9) . .
C8 C5 C1 117.03(10) . .
C8 C5 C4 84.68(10) . .
C1 C5 C4 107.60(10) . .
C8 C5 H5A 114.6 . .
C1 C5 H5A 114.6 . .
C4 C5 H5A 114.6 . .
C1 C6 H6A 109.5 . .
C1 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C1 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C4 C7 H7A 109.5 . .
C4 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C4 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
O2 C8 O1 126.70(12) . .
O2 C8 C5 137.87(14) . .
O1 C8 C5 95.38(10) . .
O3 C9 O4 124.76(11) . .
O3 C9 C2 125.87(11) . .
O4 C9 C2 109.37(9) . .
O4 C10 H10A 109.5 . .
O4 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
O4 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
O5 C11 O6 124.16(11) . .
O5 C11 C2 125.19(11) . .
O6 C11 C2 110.63(10) . .
O6 C12 H12A 109.5 . .
O6 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
O6 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C8 O1 C4 91.10(9) . .
C9 O4 C10 116.33(9) . .
C11 O6 C12 115.23(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.5272(17) .
C1 C5 1.5415(19) .
C1 C2 1.5667(18) .
C1 H1A 1.0000 .
C2 C9 1.5321(18) .
C2 C11 1.5331(17) .
C2 C3 1.5442(17) .
C3 C4 1.5137(18) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C7 1.4988(19) .
C4 O1 1.5171(16) .
C4 C5 1.544(2) .
C5 C8 1.5186(18) .
C5 H5A 1.0000 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 O2 1.1905(16) .
C8 O1 1.3687(19) .
C9 O3 1.2021(14) .
C9 O4 1.3374(16) .
C10 O4 1.4460(17) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 O5 1.1950(15) .
C11 O6 1.3408(15) .
C12 O6 1.4518(16) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 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
C6 C1 C2 C9 -153.96(10) . . . .
C5 C1 C2 C9 88.05(11) . . . .
C6 C1 C2 C11 -34.42(13) . . . .
C5 C1 C2 C11 -152.40(10) . . . .
C6 C1 C2 C3 85.06(12) . . . .
C5 C1 C2 C3 -32.93(11) . . . .
C9 C2 C3 C4 -87.74(11) . . . .
C11 C2 C3 C4 152.15(10) . . . .
C1 C2 C3 C4 32.51(11) . . . .
C2 C3 C4 C7 -157.32(11) . . . .
C2 C3 C4 O1 75.97(12) . . . .
C2 C3 C4 C5 -19.15(12) . . . .
C6 C1 C5 C8 168.31(11) . . . .
C2 C1 C5 C8 -71.48(13) . . . .
C6 C1 C5 C4 -98.68(11) . . . .
C2 C1 C5 C4 21.53(11) . . . .
C7 C4 C5 C8 -108.99(13) . . . .
C3 C4 C5 C8 114.88(10) . . . .
O1 C4 C5 C8 3.56(8) . . . .
C7 C4 C5 C1 134.31(12) . . . .
C3 C4 C5 C1 -1.82(12) . . . .
O1 C4 C5 C1 -113.14(9) . . . .
C1 C5 C8 O2 -79.72(19) . . . .
C4 C5 C8 O2 173.23(17) . . . .
C1 C5 C8 O1 103.09(11) . . . .
C4 C5 C8 O1 -3.97(9) . . . .
C11 C2 C9 O3 -120.26(12) . . . .
C3 C2 C9 O3 117.66(13) . . . .
C1 C2 C9 O3 1.44(16) . . . .
C11 C2 C9 O4 59.07(11) . . . .
C3 C2 C9 O4 -63.00(12) . . . .
C1 C2 C9 O4 -179.22(9) . . . .
C9 C2 C11 O5 -132.88(13) . . . .
C3 C2 C11 O5 -10.01(17) . . . .
C1 C2 C11 O5 105.45(14) . . . .
C9 C2 C11 O6 48.51(12) . . . .
C3 C2 C11 O6 171.37(9) . . . .
C1 C2 C11 O6 -73.17(12) . . . .
O2 C8 O1 C4 -173.63(13) . . . .
C5 C8 O1 C4 4.02(9) . . . .
C7 C4 O1 C8 118.12(12) . . . .
C3 C4 O1 C8 -111.74(11) . . . .
C5 C4 O1 C8 -3.94(9) . . . .
O3 C9 O4 C10 3.33(17) . . . .
C2 C9 O4 C10 -176.02(10) . . . .
O5 C11 O6 C12 -1.25(18) . . . .
C2 C11 O6 C12 177.38(10) . . . .
