#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/70/2017044.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_2017044
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          'C17 H20 N2 O6'
_chemical_formula_moiety         'C17 H20 N2 O6'
_chemical_formula_sum            'C17 H20 N2 O6'
_chemical_formula_weight         348.35
_chemical_name_systematic
;
tert-butyl 2-(1-hydroxyethyl)-3-(2-nitrophenyl)-5-oxo-2,5-dihydro-
1H-pyrrole-1-carboxylate
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                120.00
_cell_formula_units_Z            18
_cell_length_a                   21.1117(8)
_cell_length_b                   21.1117(8)
_cell_length_c                   20.3244(9)
_cell_measurement_reflns_used    37232
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.58
_cell_measurement_theta_min      1.93
_cell_volume                     7845.0(5)
_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_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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  0.0893
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            39673
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.26
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale violet'
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3312
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.170
_refine_ls_extinction_coef       0.00059(14)
_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   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4718
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0345P)²+5.9651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0980
_reflns_number_gt                4041
_reflns_number_total             4718
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ga3120.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               2017044
_cod_database_fobs_code          2017044
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -y,x-y,z
3 -x+y,-x,z
4 -x,-y,-z
5 y,-x+y,-z
6 x-y,x,-z
7 1/3+x,2/3+y,2/3+z
8 1/3-y,2/3+x-y,2/3+z
9 1/3-x+y,2/3-x,2/3+z
10 1/3-x,2/3-y,2/3-z
11 1/3+y,2/3-x+y,2/3-z
12 1/3+x-y,2/3+x,2/3-z
13 2/3+x,1/3+y,1/3+z
14 2/3-y,1/3+x-y,1/3+z
15 2/3-x+y,1/3-x,1/3+z
16 2/3-x,1/3-y,1/3-z
17 2/3+y,1/3-x+y,1/3-z
18 2/3+x-y,1/3+x,1/3-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
O O1 0.29424(5) 0.41562(5) 0.00122(5) 0.0391(3) Uani . . 1.000
O O2 0.21212(5) 0.28894(5) 0.07457(5) 0.0480(3) Uani . . 1.000
O O3 0.25771(5) 0.21244(4) 0.06812(4) 0.0371(3) Uani . . 1.000
O O4 0.41816(5) 0.23954(4) -0.06199(5) 0.0372(3) Uani . . 1.000
O O5 0.50360(5) 0.38580(5) 0.09835(4) 0.0417(3) Uani . . 1.000
O O6 0.56788(6) 0.33232(5) 0.09317(5) 0.0447(3) Uani . . 1.000
N N1 0.31770(5) 0.32006(5) 0.01879(5) 0.0294(3) Uani . . 1.000
N N2 0.54177(5) 0.36699(5) 0.06844(4) 0.0295(2) Uani . . 1.000
C C1 0.33427(6) 0.39007(6) -0.00134(5) 0.0287(3) Uani . . 1.000
C C2 0.40944(6) 0.42536(5) -0.02579(5) 0.0278(3) Uani . . 1.000
C C3 0.43615(5) 0.38024(5) -0.02026(5) 0.0244(2) Uani . . 1.000
C C4 0.37748(5) 0.30600(5) 0.00296(6) 0.0270(3) Uani . . 1.000
C C5 0.25675(6) 0.27380(6) 0.05644(6) 0.0320(3) Uani . . 1.000
C C6 0.20133(6) 0.15371(6) 0.10954(6) 0.0353(3) Uani . . 1.000
C C7 0.20589(10) 0.18259(9) 0.17826(7) 0.0559(5) Uani . . 1.000
C C8 0.12653(8) 0.12481(9) 0.07984(9) 0.0595(5) Uani . . 1.000
C C9 0.22464(9) 0.09680(8) 0.10738(8) 0.0513(5) Uani . . 1.000
C C10 0.35612(6) 0.24733(6) -0.05118(6) 0.0342(3) Uani . . 1.000
C C11 0.33351(8) 0.26656(8) -0.11510(8) 0.0489(4) Uani . . 1.000
C C12 0.51070(5) 0.39876(5) -0.03979(5) 0.0234(3) Uani . . 1.000
C C13 0.53620(6) 0.42848(5) -0.10190(5) 0.0273(3) Uani . . 1.000
C C14 0.60600(6) 0.44736(6) -0.12258(5) 0.0305(3) Uani . . 1.000
C C15 0.65207(6) 0.43617(6) -0.08213(6) 0.0322(3) Uani . . 1.000
C C16 0.62888(6) 0.40740(6) -0.02006(5) 0.0286(3) Uani . . 1.000
C C17 0.55966(5) 0.39000(5) -0.00005(5) 0.0243(3) Uani . . 1.000
H H2 0.43550 0.47360 -0.04310 0.0330 Uiso calc R 1.000
H H4 0.39390 0.29140 0.04350 0.0320 Uiso calc R 1.000
H H4O 0.4094(9) 0.1984(10) -0.0466(8) 0.050(4) Uiso . . 1.000
H H7A 0.19070 0.21950 0.17780 0.0840 Uiso calc R 1.000
H H7B 0.25630 0.20470 0.19420 0.0840 Uiso calc R 1.000
H H7C 0.17350 0.14230 0.20740 0.0840 Uiso calc R 1.000
H H8A 0.12740 0.11170 0.03370 0.0890 Uiso calc R 1.000
H H8B 0.11250 0.16250 0.08220 0.0890 Uiso calc R 1.000
H H8C 0.09100 0.08140 0.10420 0.0890 Uiso calc R 1.000
H H9A 0.22470 0.08200 0.06170 0.0770 Uiso calc R 1.000
H H9B 0.27390 0.11730 0.12580 0.0770 Uiso calc R 1.000
H H9C 0.19040 0.05410 0.13320 0.0770 Uiso calc R 1.000
H H10 0.31500 0.19980 -0.03470 0.0410 Uiso calc R 1.000
H H11A 0.37550 0.30970 -0.13440 0.0730 Uiso calc R 1.000
H H11B 0.31630 0.22530 -0.14570 0.0730 Uiso calc R 1.000
H H11C 0.29400 0.27720 -0.10680 0.0730 Uiso calc R 1.000
H H13 0.50510 0.43600 -0.13070 0.0330 Uiso calc R 1.000
H H14 0.62230 0.46820 -0.16500 0.0370 Uiso calc R 1.000
H H15 0.69950 0.44820 -0.09700 0.0390 Uiso calc R 1.000
H H16 0.66010 0.39970 0.00840 0.0340 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'
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 . . . 121.44(11) no
C10 O4 H4O . . . 108.6(14) no
C1 N1 C5 . . . 123.85(11) no
C4 N1 C5 . . . 124.37(10) no
C1 N1 C4 . . . 111.29(10) no
O5 N2 O6 . . . 123.86(10) no
O6 N2 C17 . . . 118.15(10) no
O5 N2 C17 . . . 117.93(10) no
O1 C1 N1 . . . 126.66(12) no
N1 C1 C2 . . . 105.79(11) no
O1 C1 C2 . . . 127.56(10) no
C1 C2 C3 . . . 110.28(9) no
C2 C3 C12 . . . 124.42(9) no
C4 C3 C12 . . . 124.99(9) no
C2 C3 C4 . . . 110.39(10) no
N1 C4 C10 . . . 112.45(10) no
C3 C4 C10 . . . 111.66(10) no
N1 C4 C3 . . . 101.58(8) no
O2 C5 N1 . . . 123.91(11) no
O3 C5 N1 . . . 108.86(11) no
O2 C5 O3 . . . 127.24(12) no
O3 C6 C7 . . . 109.05(10) no
O3 C6 C9 . . . 101.81(11) no
C7 C6 C8 . . . 112.16(14) no
O3 C6 C8 . . . 110.67(11) no
C8 C6 C9 . . . 111.04(12) no
C7 C6 C9 . . . 111.62(13) no
O4 C10 C11 . . . 109.46(11) no
C4 C10 C11 . . . 113.72(10) no
O4 C10 C4 . . . 106.69(10) no
C3 C12 C17 . . . 124.93(9) no
C13 C12 C17 . . . 116.07(11) no
C3 C12 C13 . . . 118.99(10) no
C12 C13 C14 . . . 121.37(11) no
C13 C14 C15 . . . 120.59(10) no
C14 C15 C16 . . . 119.64(13) no
C15 C16 C17 . . . 118.87(12) no
N2 C17 C16 . . . 115.68(10) no
C12 C17 C16 . . . 123.44(10) no
N2 C17 C12 . . . 120.69(10) no
C1 C2 H2 . . . 125.00 no
C3 C2 H2 . . . 125.00 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 . . . 110.00 no
C6 C8 H8A . . . 110.00 no
C6 C8 H8B . . . 109.00 no
C6 C8 H8C . . . 109.00 no
H8A C8 H8B . . . 109.00 no
H8A C8 H8C . . . 109.00 no
H8B C8 H8C . . . 110.00 no
C6 C9 H9A . . . 110.00 no
C6 C9 H9B . . . 110.00 no
C6 C9 H9C . . . 109.00 no
H9A C9 H9B . . . 109.00 no
H9A C9 H9C . . . 109.00 no
H9B C9 H9C . . . 110.00 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 . . . 110.00 no
C10 C11 H11C . . . 109.00 no
H11A C11 H11B . . . 109.00 no
H11A C11 H11C . . . 109.00 no
H11B C11 H11C . . . 109.00 no
C12 C13 H13 . . . 119.00 no
C14 C13 H13 . . . 119.00 no
C13 C14 H14 . . . 120.00 no
C15 C14 H14 . . . 120.00 no
C14 C15 H15 . . . 120.00 no
C16 C15 H15 . . . 120.00 no
C15 C16 H16 . . . 121.00 no
C17 C16 H16 . . . 121.00 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
O1 C1 . . 1.2098(18) no
O2 C5 . . 1.1945(18) no
O3 C5 . . 1.3271(15) no
O3 C6 . . 1.4788(15) no
O4 C10 . . 1.4164(18) no
O5 N2 . . 1.2234(15) no
O6 N2 . . 1.2230(16) no
O4 H4O . . 0.852(18) no
N1 C1 . . 1.3990(15) no
N1 C5 . . 1.3923(16) no
N1 C4 . . 1.4694(17) no
N2 C17 . . 1.4604(13) no
C1 C2 . . 1.4622(18) no
C2 C3 . . 1.3323(16) no
C3 C12 . . 1.4738(16) no
C3 C4 . . 1.5074(14) no
C4 C10 . . 1.5459(16) no
C6 C8 . . 1.506(2) no
C6 C9 . . 1.510(2) no
C6 C7 . . 1.5077(19) no
C10 C11 . . 1.508(2) no
C12 C17 . . 1.3950(16) no
C12 C13 . . 1.3926(14) no
C13 C14 . . 1.3855(19) no
C14 C15 . . 1.3811(19) no
C15 C16 . . 1.3794(16) no
C16 C17 . . 1.3781(18) no
C2 H2 . . 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 . . 0.9800 no
C11 H11B . . 0.9800 no
C11 H11C . . 0.9800 no
C13 H13 . . 0.9500 no
C14 H14 . . 0.9500 no
C15 H15 . . 0.9500 no
C16 H16 . . 0.9500 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 5_555 0.852(18) 1.930(19) 2.7600(15) 164.3(19) 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 . . . . -2.40(19) no
C6 O3 C5 N1 . . . . 177.35(10) no
C5 O3 C6 C7 . . . . -62.67(16) no
C5 O3 C6 C8 . . . . 61.16(14) no
C5 O3 C6 C9 . . . . 179.26(11) no
C4 N1 C1 O1 . . . . 175.08(11) no
C4 N1 C1 C2 . . . . -4.97(12) no
C5 N1 C1 O1 . . . . -12.66(19) no
C5 N1 C1 C2 . . . . 167.29(10) no
C1 N1 C4 C3 . . . . 7.80(12) no
C1 N1 C4 C10 . . . . -111.70(10) no
C5 N1 C4 C3 . . . . -164.42(10) no
C5 N1 C4 C10 . . . . 76.09(14) no
C1 N1 C5 O2 . . . . 0.98(19) no
C1 N1 C5 O3 . . . . -178.78(10) no
C4 N1 C5 O2 . . . . 172.23(12) no
C4 N1 C5 O3 . . . . -7.52(16) no
O5 N2 C17 C12 . . . . -31.70(14) no
O5 N2 C17 C16 . . . . 143.49(11) no
O6 N2 C17 C12 . . . . 150.83(10) no
O6 N2 C17 C16 . . . . -33.99(14) no
O1 C1 C2 C3 . . . . 179.47(11) no
N1 C1 C2 C3 . . . . -0.48(12) no
C1 C2 C3 C4 . . . . 5.58(12) no
C1 C2 C3 C12 . . . . -179.43(9) no
C2 C3 C4 N1 . . . . -8.07(12) no
C2 C3 C4 C10 . . . . 111.98(11) no
C12 C3 C4 N1 . . . . 176.97(10) no
C12 C3 C4 C10 . . . . -62.99(14) no
C2 C3 C12 C13 . . . . -49.77(14) no
C2 C3 C12 C17 . . . . 129.10(11) no
C4 C3 C12 C13 . . . . 124.51(11) no
C4 C3 C12 C17 . . . . -56.63(15) no
N1 C4 C10 O4 . . . . 179.54(9) no
N1 C4 C10 C11 . . . . 58.76(14) no
C3 C4 C10 O4 . . . . 66.10(12) no
C3 C4 C10 C11 . . . . -54.68(15) no
C3 C12 C13 C14 . . . . 179.54(9) no
C17 C12 C13 C14 . . . . 0.57(14) no
C3 C12 C17 N2 . . . . -5.69(14) no
C3 C12 C17 C16 . . . . 179.51(10) no
C13 C12 C17 N2 . . . . 173.20(9) no
C13 C12 C17 C16 . . . . -1.60(14) no
C12 C13 C14 C15 . . . . 0.89(16) no
C13 C14 C15 C16 . . . . -1.41(17) no
C14 C15 C16 C17 . . . . 0.42(16) no
C15 C16 C17 N2 . . . . -173.92(9) no
C15 C16 C17 C12 . . . . 1.12(16) no
