#------------------------------------------------------------------------------
#$Date: 2021-11-06 20:36:17 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270346 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/91/7129105.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_7129105
loop_
_publ_author_name
'Del Río-Rodríguez, Roberto'
'Laina-Martín, Víctor'
'Fernández-Salas, Jose A'
'Alemán, José'
_publ_section_title
;
 Enantioselective vinylogous Mukaiyama aldol reaction of α-ketoesters
 under bifunctional organocatalysis.
;
_journal_issue                   88
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11665
_journal_page_last               11668
_journal_paper_doi               10.1039/d1cc04263g
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H13 Br O3'
_chemical_formula_weight         285.13
_chemical_name_common            RR-626-F1_200K
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc28jcsz
_audit_update_record
;
2021-08-03 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.8320(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3815(2)
_cell_length_b                   7.13240(10)
_cell_length_c                   10.0251(2)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      26.1462
_cell_measurement_theta_min      2.5026
_cell_volume                     581.92(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22324
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.09
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    3.521
_exptl_absorpt_correction_T_max  0.80
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.295
_refine_ls_abs_structure_details
;

Flack x determined using 906 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2111
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.0195
_refine_ls_R_factor_gt           0.0183
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0223P)²+0.1857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0462
_refine_ls_wR_factor_ref         0.0547
_reflns_number_gt                2051
_reflns_number_total             2111
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc04263g2.cif
_cod_data_source_block           03363
_cod_depositor_comments          'Adding full bibliography for 7129105.cif.'
_cod_database_code               7129105
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 -0.12221(4) 0.01906(8) 0.76130(4) 0.05028(14) Uani d . . . 1 . .
C C1 0.5415(5) 0.5982(5) 0.5775(4) 0.0352(8) Uani d . . . 1 . .
C C2 0.6765(4) 0.4976(8) 0.6758(4) 0.0452(9) Uani d . . . 1 . .
H H2A 0.776193 0.577061 0.693162 0.054 Uiso calc U . R 1 . .
H H2B 0.701529 0.380941 0.631267 0.054 Uiso calc U . R 1 . .
C C3 0.6415(5) 0.4464(6) 0.8137(4) 0.0440(9) Uani d . . . 1 . .
H H3A 0.573179 0.331645 0.804012 0.053 Uiso calc U . R 1 . .
H H3B 0.745843 0.421539 0.882118 0.053 Uiso calc U . R 1 . .
C C4 0.5517(5) 0.6081(6) 0.8614(4) 0.0389(8) Uani d . . . 1 . .
H H4A 0.621211 0.721886 0.871835 0.047 Uiso calc U . R 1 . .
H H4B 0.530989 0.577818 0.952154 0.047 Uiso calc U . R 1 . .
C C5 0.3895(4) 0.6466(5) 0.7595(3) 0.0314(7) Uani d . . . 1 . .
C C6 0.2634(4) 0.4928(6) 0.7566(3) 0.0290(7) Uani d . . . 1 . .
C C7 0.2164(5) 0.4458(5) 0.8772(4) 0.0396(9) Uani d . . . 1 . .
H H7 0.263725 0.511187 0.959742 0.048 Uiso calc U . R 1 . .
C C8 0.1021(5) 0.3060(6) 0.8787(4) 0.0405(9) Uani d . . . 1 . .
H H8 0.071568 0.275225 0.961414 0.049 Uiso calc U . R 1 . .
C C9 0.0334(4) 0.2123(5) 0.7586(4) 0.0347(8) Uani d . . . 1 . .
C C10 0.0741(5) 0.2565(5) 0.6380(4) 0.0384(8) Uani d . . . 1 . .
H H10 0.024327 0.191984 0.555614 0.046 Uiso calc U . R 1 . .
C C11 0.1887(5) 0.3964(5) 0.6375(3) 0.0344(8) Uani d . . . 1 . .
H H11 0.216902 0.42719 0.553785 0.041 Uiso calc U . R 1 . .
C C12 0.3177(5) 0.8357(5) 0.7864(4) 0.0416(9) Uani d . . . 1 . .
H H12A 0.220153 0.862584 0.711072 0.05 Uiso calc U . R 1 . .
H H12B 0.280777 0.828018 0.872937 0.05 Uiso calc U . R 1 . .
O O1 0.4132(3) 0.6681(4) 0.6196(2) 0.0338(5) Uani d . . . 1 . .
O O2 0.5421(4) 0.6257(5) 0.4588(3) 0.0554(8) Uani d . . . 1 . .
O O3 0.4306(4) 0.9853(4) 0.7963(3) 0.0520(8) Uani d . . . 1 . .
H H3O 0.435225 1.019407 0.717114 0.078 Uiso calc U . R 1 . .
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'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 C1 O1 . . 116.3(4) ?
O2 C1 C2 . . 123.1(3) ?
O1 C1 C2 . . 120.6(3) ?
C1 C2 C3 . . 115.7(3) ?
C4 C3 C2 . . 108.7(3) ?
C3 C4 C5 . . 111.0(3) ?
O1 C5 C4 . . 110.9(3) ?
O1 C5 C6 . . 108.0(3) ?
C4 C5 C6 . . 112.9(3) ?
O1 C5 C12 . . 103.0(3) ?
C4 C5 C12 . . 111.6(3) ?
C6 C5 C12 . . 109.9(3) ?
C11 C6 C7 . . 117.5(3) ?
C11 C6 C5 . . 122.8(3) ?
C7 C6 C5 . . 119.7(3) ?
C8 C7 C6 . . 121.3(3) ?
C9 C8 C7 . . 119.0(3) ?
C10 C9 C8 . . 121.3(4) ?
C10 C9 Br1 . . 119.7(3) ?
C8 C9 Br1 . . 119.0(3) ?
C9 C10 C11 . . 119.2(3) ?
C10 C11 C6 . . 121.5(3) ?
O3 C12 C5 . . 113.2(3) ?
C1 O1 C5 . . 124.2(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C9 . 1.902(4) ?
C1 O2 . 1.208(5) ?
C1 O1 . 1.341(4) ?
C1 C2 . 1.495(6) ?
C2 C3 . 1.525(6) ?
C3 C4 . 1.516(5) ?
C4 C5 . 1.517(5) ?
C5 O1 . 1.471(4) ?
C5 C6 . 1.519(5) ?
C5 C12 . 1.527(5) ?
C6 C11 . 1.390(5) ?
C6 C7 . 1.400(5) ?
C7 C8 . 1.385(5) ?
C8 C9 . 1.377(5) ?
C9 C10 . 1.370(5) ?
C10 C11 . 1.386(5) ?
C12 O3 . 1.414(5) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2B Br1 1_655 0.99 3.10 3.813(5) 129.8 ?
C4 H4B O3 2_647 0.99 2.55 3.510(5) 163.0 ?
O3 H3O O2 2_656 0.84 1.97 2.806(4) 173.5 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 C1 C2 C3 . . . . -169.8(4) ?
O1 C1 C2 C3 . . . . 12.0(6) ?
C1 C2 C3 C4 . . . . -40.2(5) ?
C2 C3 C4 C5 . . . . 60.7(4) ?
C3 C4 C5 O1 . . . . -51.8(4) ?
C3 C4 C5 C6 . . . . 69.6(4) ?
C3 C4 C5 C12 . . . . -166.0(3) ?
O1 C5 C6 C11 . . . . -0.3(4) ?
C4 C5 C6 C11 . . . . -123.3(4) ?
C12 C5 C6 C11 . . . . 111.4(4) ?
O1 C5 C6 C7 . . . . -179.1(3) ?
C4 C5 C6 C7 . . . . 57.9(4) ?
C12 C5 C6 C7 . . . . -67.4(4) ?
C11 C6 C7 C8 . . . . 1.3(6) ?
C5 C6 C7 C8 . . . . -179.8(3) ?
C6 C7 C8 C9 . . . . -0.2(6) ?
C7 C8 C9 C10 . . . . -1.0(6) ?
C7 C8 C9 Br1 . . . . 179.5(3) ?
C8 C9 C10 C11 . . . . 1.1(6) ?
Br1 C9 C10 C11 . . . . -179.5(3) ?
C9 C10 C11 C6 . . . . 0.1(5) ?
C7 C6 C11 C10 . . . . -1.2(5) ?
C5 C6 C11 C10 . . . . 180.0(3) ?
O1 C5 C12 O3 . . . . -67.6(4) ?
C4 C5 C12 O3 . . . . 51.5(4) ?
C6 C5 C12 O3 . . . . 177.5(3) ?
O2 C1 O1 C5 . . . . 179.0(3) ?
C2 C1 O1 C5 . . . . -2.7(5) ?
C4 C5 O1 C1 . . . . 22.6(5) ?
C6 C5 O1 C1 . . . . -101.6(3) ?
C12 C5 O1 C1 . . . . 142.2(3) ?
