#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/70/2017046.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2017046
loop_
_publ_author_name
'Vallat, Olivier'
'Buciumas, Ana-Maria'
'Neier, Reinhard'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 5-Hydroxyalkyl derivatives of tert-butyl
 2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate:
 diastereoselectivity of the Mukaiyama crossed-aldol-type reaction
;
_journal_coeditor_code           GA3120
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o171
_journal_page_last               o175
_journal_paper_doi               10.1107/S0108270109008877
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H20 Br N O4'
_chemical_formula_moiety         'C13 H20 Br N O4'
_chemical_formula_sum            'C13 H20 Br N O4'
_chemical_formula_weight         334.21
_chemical_name_systematic
;
tert-butyl
2-(4-bromo-1-hydroxybutyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.176(7)
_cell_angle_beta                 113.759(7)
_cell_angle_gamma                101.367(8)
_cell_formula_units_Z            2
_cell_length_a                   8.8340(9)
_cell_length_b                   9.0750(9)
_cell_length_c                   10.7283(10)
_cell_measurement_reflns_used    12982
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.74
_cell_measurement_theta_min      2.23
_cell_volume                     719.57(14)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2006)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2006)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2006)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON  (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 0.81\%A
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       'φ and ω'
_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  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9956
_diffrn_reflns_theta_full        29.20
_diffrn_reflns_theta_max         29.20
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.866
_exptl_absorpt_correction_T_max  0.47217
_exptl_absorpt_correction_T_min  0.30730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULscanABS in PLATON; Spek, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.779
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0236P)²+0.4857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0662
_reflns_number_gt                3587
_reflns_number_total             3862
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ga3120.cif
_cod_data_source_block           III
_cod_original_cell_volume        719.57(12)
_cod_database_code               2017046
_cod_database_fobs_code          2017046
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Br Br1 1.47778(2) 0.30287(2) 1.13729(2) 0.03290(10) Uani . . 1.000
O O1 0.31030(14) -0.11093(15) 0.53882(12) 0.0262(3) Uani . . 1.000
O O2 0.52777(14) -0.25263(14) 0.45870(12) 0.0245(3) Uani . . 1.000
O O3 0.80224(14) -0.16522(13) 0.64932(12) 0.0231(3) Uani . . 1.000
O O4 0.82532(15) 0.30771(13) 0.76664(12) 0.0245(3) Uani . . 1.000
N N1 0.61400(16) -0.04621(15) 0.67145(13) 0.0192(3) Uani . . 1.000
C C1 0.44905(19) -0.03668(18) 0.64902(16) 0.0211(4) Uani . . 1.000
C C2 0.4806(2) 0.0789(2) 0.78665(18) 0.0247(4) Uani . . 1.000
C C3 0.6499(2) 0.13381(19) 0.88148(17) 0.0236(4) Uani . . 1.000
C C4 0.75282(19) 0.06297(18) 0.81779(15) 0.0201(3) Uani . . 1.000
C C5 0.63877(19) -0.16534(17) 0.58003(16) 0.0200(3) Uani . . 1.000
C C6 0.8667(2) -0.28116(19) 0.57988(17) 0.0230(4) Uani . . 1.000
C C7 0.7644(3) -0.4500(2) 0.5536(2) 0.0342(5) Uani . . 1.000
C C8 0.8571(3) -0.2594(2) 0.4414(2) 0.0336(5) Uani . . 1.000
C C9 1.0554(2) -0.2308(3) 0.6973(2) 0.0385(6) Uani . . 1.000
C C10 0.89225(19) 0.19009(18) 0.81204(16) 0.0200(3) Uani . . 1.000
C C11 1.05272(19) 0.27493(19) 0.96104(16) 0.0229(4) Uani . . 1.000
C C12 1.1980(2) 0.39234(19) 0.95675(17) 0.0240(4) Uani . . 1.000
C C13 1.3675(2) 0.46521(19) 1.09855(17) 0.0244(4) Uani . . 1.000
H H4 0.81030 -0.00080 0.87430 0.0240 Uiso calc R 1.000
H H2 0.39270 0.10970 0.80500 0.0300 Uiso calc R 1.000
H H3 0.69970 0.20910 0.97810 0.0280 Uiso calc R 1.000
H H4O 0.75420 0.26750 0.67690 0.0370 Uiso calc R 1.000
H H7A 0.76700 -0.45500 0.64460 0.0510 Uiso calc R 1.000
H H7B 0.64260 -0.47870 0.47880 0.0510 Uiso calc R 1.000
H H7C 0.81720 -0.52580 0.52020 0.0510 Uiso calc R 1.000
H H8A 0.91190 -0.14520 0.46220 0.0500 Uiso calc R 1.000
H H8B 0.73400 -0.29600 0.36660 0.0500 Uiso calc R 1.000
H H8C 0.91910 -0.32290 0.40610 0.0500 Uiso calc R 1.000
H H9A 1.05770 -0.24010 0.78710 0.0580 Uiso calc R 1.000
H H9B 1.11690 -0.11880 0.71640 0.0580 Uiso calc R 1.000
H H9C 1.11350 -0.30100 0.66420 0.0580 Uiso calc R 1.000
H H10 0.92810 0.13480 0.74120 0.0240 Uiso calc R 1.000
H H11A 1.09730 0.19350 0.99690 0.0270 Uiso calc R 1.000
H H11B 1.01900 0.33430 1.03060 0.0270 Uiso calc R 1.000
H H12A 1.22070 0.33530 0.87830 0.0290 Uiso calc R 1.000
H H12B 1.15710 0.48030 0.93160 0.0290 Uiso calc R 1.000
H H13A 1.34380 0.51190 1.17960 0.0290 Uiso calc R 1.000
H H13B 1.44870 0.55330 1.09370 0.0290 Uiso calc R 1.000
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'
N N 0.0061 0.0033 '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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 O3 C6 . . . 121.31(12) no
C10 O4 H4O . . . 109.00 no
C1 N1 C4 . . . 111.34(13) no
C4 N1 C5 . . . 123.47(14) no
C1 N1 C5 . . . 124.00(13) no
O1 C1 N1 . . . 126.53(15) no
N1 C1 C2 . . . 105.51(14) no
O1 C1 C2 . . . 127.96(17) no
C1 C2 C3 . . . 109.86(17) no
C2 C3 C4 . . . 111.62(15) no
N1 C4 C10 . . . 112.27(12) no
C3 C4 C10 . . . 113.40(14) no
N1 C4 C3 . . . 101.63(14) no
O2 C5 N1 . . . 124.16(17) no
O3 C5 N1 . . . 108.81(13) no
O2 C5 O3 . . . 127.03(16) no
O3 C6 C7 . . . 109.20(16) no
O3 C6 C8 . . . 110.36(15) no
C7 C6 C8 . . . 112.91(14) no
C7 C6 C9 . . . 111.11(17) no
O3 C6 C9 . . . 101.43(14) no
C8 C6 C9 . . . 111.24(18) no
O4 C10 C11 . . . 108.24(13) no
C4 C10 C11 . . . 110.71(13) no
O4 C10 C4 . . . 111.18(15) no
C10 C11 C12 . . . 112.01(13) no
C11 C12 C13 . . . 113.79(14) no
Br1 C13 C12 . . . 111.00(12) no
C1 C2 H2 . . . 125.00 no
C3 C2 H2 . . . 125.00 no
C2 C3 H3 . . . 124.00 no
C4 C3 H3 . . . 124.00 no
N1 C4 H4 . . . 110.00 no
C3 C4 H4 . . . 110.00 no
C10 C4 H4 . . . 110.00 no
C6 C7 H7A . . . 109.00 no
C6 C7 H7B . . . 109.00 no
C6 C7 H7C . . . 109.00 no
H7A C7 H7B . . . 110.00 no
H7A C7 H7C . . . 109.00 no
H7B C7 H7C . . . 109.00 no
C6 C8 H8A . . . 109.00 no
C6 C8 H8B . . . 109.00 no
C6 C8 H8C . . . 109.00 no
H8A C8 H8B . . . 109.00 no
H8A C8 H8C . . . 110.00 no
H8B C8 H8C . . . 110.00 no
C6 C9 H9A . . . 109.00 no
C6 C9 H9B . . . 109.00 no
C6 C9 H9C . . . 109.00 no
H9A C9 H9B . . . 109.00 no
H9A C9 H9C . . . 109.00 no
H9B C9 H9C . . . 109.00 no
O4 C10 H10 . . . 109.00 no
C4 C10 H10 . . . 109.00 no
C11 C10 H10 . . . 109.00 no
C10 C11 H11A . . . 109.00 no
C10 C11 H11B . . . 109.00 no
C12 C11 H11A . . . 109.00 no
C12 C11 H11B . . . 109.00 no
H11A C11 H11B . . . 108.00 no
C11 C12 H12A . . . 109.00 no
C11 C12 H12B . . . 109.00 no
C13 C12 H12A . . . 109.00 no
C13 C12 H12B . . . 109.00 no
H12A C12 H12B . . . 108.00 no
Br1 C13 H13A . . . 109.00 no
Br1 C13 H13B . . . 109.00 no
C12 C13 H13A . . . 109.00 no
C12 C13 H13B . . . 109.00 no
H13A C13 H13B . . . 108.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C13 . . 1.9575(19) no
O1 C1 . . 1.213(2) no
O2 C5 . . 1.2015(19) no
O3 C5 . . 1.331(2) no
O3 C6 . . 1.477(2) no
O4 C10 . . 1.413(2) no
O4 H4O . . 0.8400 no
N1 C4 . . 1.4691(19) no
N1 C5 . . 1.388(2) no
N1 C1 . . 1.402(2) no
C1 C2 . . 1.467(2) no
C2 C3 . . 1.324(3) no
C3 C4 . . 1.491(3) no
C4 C10 . . 1.545(2) no
C6 C8 . . 1.517(3) no
C6 C9 . . 1.517(3) no
C6 C7 . . 1.510(3) no
C10 C11 . . 1.516(2) no
C11 C12 . . 1.522(3) no
C12 C13 . . 1.508(2) no
C2 H2 . . 0.9500 no
C3 H3 . . 0.9500 no
C4 H4 . . 1.0000 no
C7 H7A . . 0.9800 no
C7 H7B . . 0.9800 no
C7 H7C . . 0.9800 no
C8 H8A . . 0.9800 no
C8 H8B . . 0.9800 no
C8 H8C . . 0.9800 no
C9 H9A . . 0.9800 no
C9 H9B . . 0.9800 no
C9 H9C . . 0.9800 no
C10 H10 . . 1.0000 no
C11 H11A . . 0.9900 no
C11 H11B . . 0.9900 no
C12 H12A . . 0.9900 no
C12 H12B . . 0.9900 no
C13 H13A . . 0.9900 no
C13 H13B . . 0.9900 no
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
O4 H4O O1 2_656 0.84 2.17 2.9138(16) 148.00 yes
O4 H4O O2 2_656 0.84 2.28 2.9225(18) 134.00 yes
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
C6 O3 C5 O2 . . . . -0.7(3) no
C6 O3 C5 N1 . . . . 179.11(13) no
C5 O3 C6 C7 . . . . -64.05(19) no
C5 O3 C6 C8 . . . . 60.6(2) no
C5 O3 C6 C9 . . . . 178.60(16) no
C4 N1 C1 O1 . . . . 179.21(17) no
C4 N1 C1 C2 . . . . -1.66(18) no
C5 N1 C1 O1 . . . . -12.9(3) no
C5 N1 C1 C2 . . . . 166.25(15) no
C1 N1 C4 C3 . . . . 2.02(17) no
C1 N1 C4 C10 . . . . -119.46(16) no
C5 N1 C4 C3 . . . . -165.97(15) no
C5 N1 C4 C10 . . . . 72.6(2) no
C1 N1 C5 O2 . . . . 15.6(3) no
C1 N1 C5 O3 . . . . -164.30(14) no
C4 N1 C5 O2 . . . . -177.97(16) no
C4 N1 C5 O3 . . . . 2.2(2) no
O1 C1 C2 C3 . . . . 179.65(18) no
N1 C1 C2 C3 . . . . 0.5(2) no
C1 C2 C3 C4 . . . . 0.8(2) no
C2 C3 C4 N1 . . . . -1.68(19) no
C2 C3 C4 C10 . . . . 119.01(16) no
N1 C4 C10 O4 . . . . 72.57(17) no
N1 C4 C10 C11 . . . . -167.08(14) no
C3 C4 C10 O4 . . . . -41.91(17) no
C3 C4 C10 C11 . . . . 78.44(17) no
O4 C10 C11 C12 . . . . -62.07(19) no
C4 C10 C11 C12 . . . . 175.84(14) no
C10 C11 C12 C13 . . . . -173.35(15) no
C11 C12 C13 Br1 . . . . 68.73(17) no
