#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/21/7102172.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_7102172
loop_
_publ_author_name
'Alemán, José'
'Reyes, Efraím'
'Richter, Bo'
'Overgaard, Jacob'
'Jørgensen, Karl Anker'
_publ_section_title
;
 Organocatalytic asymmetric "anti-Michael" reaction of beta-ketoesters.
;
_journal_issue                   38
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3921
_journal_page_last               3923
_journal_paper_doi               10.1039/b710393j
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H19 N1 O3'
_chemical_formula_sum            'C18 H19 N O3'
_chemical_formula_weight         297.34
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2007-06-15T13:08:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 97.319(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2084(2)
_cell_length_b                   10.3461(3)
_cell_length_c                   12.6475(3)
_cell_measurement_reflns_used    8707
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      55.38
_cell_measurement_theta_min      3.523
_cell_measurement_wavelength     0.71073
_cell_volume                     805.76(4)
_computing_cell_refinement       'Saint+ (Bruker-Nonius, 2006)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2006)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 0.0833
_diffrn_measured_fraction_theta_full 0.865
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method       'φ-scans and ω-scans'
_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
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1687
_diffrn_reflns_theta_full        56.11
_diffrn_reflns_theta_max         56.11
_diffrn_reflns_theta_min         7.6
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.03
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 719 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       0.0111(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         1687
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0471P)²+0.1100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0778
_reflns_number_gt                1661
_reflns_number_total             1687
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b710393j.txt
_cod_data_source_block           07jo0022_0m
_cod_database_code               7102172
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
C1 C 0.8711(4) 0.5364(2) 0.14053(16) 0.0274(6) Uani 1 1 d .
C2 C 0.9088(4) 0.2988(2) 0.12985(18) 0.0361(7) Uani 1 1 d .
H2 H 1.0361 0.3127 0.0969 0.043 Uiso 1 1 calc R
C3 C 0.8386(5) 0.1742(3) 0.1445(2) 0.0439(7) Uani 1 1 d .
H3 H 0.918 0.1026 0.1228 0.053 Uiso 1 1 calc R
C4 C 0.6515(5) 0.1545(3) 0.1912(2) 0.0472(7) Uani 1 1 d .
H4 H 0.601 0.069 0.2002 0.057 Uiso 1 1 calc R
C5 C 0.5378(4) 0.2579(2) 0.22480(19) 0.0387(7) Uani 1 1 d .
H5 H 0.4102 0.2429 0.2572 0.046 Uiso 1 1 calc R
C6 C 0.4831(4) 0.4969(2) 0.24816(18) 0.0328(6) Uani 1 1 d .
H6A H 0.5337 0.5146 0.3242 0.039 Uiso 1 1 calc R
H6B H 0.327 0.4743 0.242 0.039 Uiso 1 1 calc R
C7 C 0.5110(3) 0.6189(2) 0.18267(18) 0.0296(6) Uani 1 1 d .
H7A H 0.4366 0.6924 0.2128 0.036 Uiso 1 1 calc R
H7B H 0.4432 0.6055 0.1083 0.036 Uiso 1 1 calc R
C8 C 0.7528(3) 0.6509(2) 0.18368(17) 0.0253(6) Uani 1 1 d .
C9 C 0.7949(4) 0.4042(2) 0.16289(16) 0.0275(6) Uani 1 1 d .
C10 C 0.6075(4) 0.3842(3) 0.21177(16) 0.0301(6) Uani 1 1 d .
C11 C 0.7873(4) 0.7735(2) 0.12034(17) 0.0287(6) Uani 1 1 d .
C12 C 0.9986(5) 0.8314(3) 0.14004(18) 0.0326(6) Uani 1 1 d .
C13 C 0.6391(4) 0.8304(3) 0.05166(17) 0.0361(6) Uani 1 1 d .
H13A H 0.6738 0.9077 0.0169 0.043 Uiso 1 1 calc R
H13B H 0.4979 0.7942 0.0371 0.043 Uiso 1 1 calc R
C14 C 0.8544(4) 0.6717(2) 0.29976(18) 0.0279(6) Uani 1 1 d .
C15 C 0.8458(4) 0.8240(3) 0.44878(17) 0.0344(6) Uani 1 1 d .
C16 C 1.0866(4) 0.8515(3) 0.4598(2) 0.0500(8) Uani 1 1 d .
H16A H 1.1157 0.9172 0.4077 0.075 Uiso 1 1 calc R
H16B H 1.165 0.772 0.447 0.075 Uiso 1 1 calc R
H16C H 1.1353 0.8831 0.532 0.075 Uiso 1 1 calc R
C17 C 0.7158(4) 0.9480(3) 0.4521(2) 0.0495(8) Uani 1 1 d .
H17A H 0.5605 0.9274 0.4448 0.074 Uiso 1 1 calc R
H17B H 0.7451 1.0046 0.3935 0.074 Uiso 1 1 calc R
H17C H 0.7578 0.9919 0.5203 0.074 Uiso 1 1 calc R
C18 C 0.7871(5) 0.7271(3) 0.5289(2) 0.0583(9) Uani 1 1 d .
H18A H 0.6312 0.7085 0.5154 0.087 Uiso 1 1 calc R
H18B H 0.8222 0.7624 0.6009 0.087 Uiso 1 1 calc R
H18C H 0.8694 0.6473 0.5226 0.087 Uiso 1 1 calc R
N1 N 1.1644(4) 0.8815(2) 0.16000(17) 0.0455(6) Uani 1 1 d .
O1 O 1.0215(2) 0.55444(16) 0.08890(12) 0.0345(5) Uani 1 1 d .
O2 O 0.9893(3) 0.60103(17) 0.34553(12) 0.0399(5) Uani 1 1 d .
O3 O 0.7711(2) 0.77646(16) 0.33909(11) 0.0308(4) 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 C9 121.7(2)
O1 C1 C8 120.5(2)
C9 C1 C8 117.76(19)
C3 C2 C9 120.6(2)
C3 C2 H2 119.7
C9 C2 H2 119.7
C2 C3 C4 119.5(3)
C2 C3 H3 120.3
C4 C3 H3 120.3
C5 C4 C3 120.5(3)
C5 C4 H4 119.7
C3 C4 H4 119.7
C4 C5 C10 120.8(2)
C4 C5 H5 119.6
C10 C5 H5 119.6
C10 C6 C7 112.07(18)
C10 C6 H6A 109.2
C7 C6 H6A 109.2
C10 C6 H6B 109.2
C7 C6 H6B 109.2
H6A C6 H6B 107.9
C6 C7 C8 110.55(18)
C6 C7 H7A 109.5
C8 C7 H7A 109.5
C6 C7 H7B 109.5
C8 C7 H7B 109.5
H7A C7 H7B 108.1
C11 C8 C1 110.45(18)
C11 C8 C7 112.10(18)
C1 C8 C7 110.07(19)
C11 C8 C14 108.47(18)
C1 C8 C14 106.95(17)
C7 C8 C14 108.63(18)
C2 C9 C10 119.9(2)
C2 C9 C1 118.54(19)
C10 C9 C1 121.5(2)
C5 C10 C9 118.6(2)
C5 C10 C6 120.8(2)
C9 C10 C6 120.6(2)
C13 C11 C12 118.2(2)
C13 C11 C8 125.6(2)
C12 C11 C8 116.2(2)
N1 C12 C11 176.5(3)
C11 C13 H13A 120
C11 C13 H13B 120
H13A C13 H13B 120
O2 C14 O3 126.7(2)
O2 C14 C8 123.4(2)
O3 C14 C8 109.92(19)
O3 C15 C18 109.5(2)
O3 C15 C16 109.60(18)
C18 C15 C16 112.7(2)
O3 C15 C17 101.63(18)
C18 C15 C17 111.6(2)
C16 C15 C17 111.2(2)
C15 C16 H16A 109.5
C15 C16 H16B 109.5
H16A C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C15 C17 H17A 109.5
C15 C17 H17B 109.5
H17A C17 H17B 109.5
C15 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C15 C18 H18A 109.5
C15 C18 H18B 109.5
H18A C18 H18B 109.5
C15 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C14 O3 C15 122.01(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.220(3)
C1 C9 1.486(3)
C1 C8 1.531(3)
C2 C3 1.381(4)
C2 C9 1.393(3)
C2 H2 0.95
C3 C4 1.383(4)
C3 H3 0.95
C4 C5 1.379(4)
C4 H4 0.95
C5 C10 1.393(4)
C5 H5 0.95
C6 C10 1.502(3)
C6 C7 1.532(3)
C6 H6A 0.99
C6 H6B 0.99
C7 C8 1.536(3)
C7 H7A 0.99
C7 H7B 0.99
C8 C11 1.529(3)
C8 C14 1.537(3)
C9 C10 1.401(3)
C11 C13 1.321(3)
C11 C12 1.435(4)
C12 N1 1.151(3)
C13 H13A 0.95
C13 H13B 0.95
C14 O2 1.203(3)
C14 O3 1.325(3)
C15 O3 1.489(3)
C15 C18 1.503(4)
C15 C16 1.510(3)
C15 C17 1.519(4)
C16 H16A 0.98
C16 H16B 0.98
C16 H16C 0.98
C17 H17A 0.98
C17 H17B 0.98
C17 H17C 0.98
C18 H18A 0.98
C18 H18B 0.98
C18 H18C 0.98
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
C9 C2 C3 C4 0.9(4)
C2 C3 C4 C5 -1.2(4)
C3 C4 C5 C10 0.5(4)
C10 C6 C7 C8 -54.6(2)
O1 C1 C8 C11 21.4(3)
C9 C1 C8 C11 -158.06(18)
O1 C1 C8 C7 145.67(18)
C9 C1 C8 C7 -33.8(2)
O1 C1 C8 C14 -96.5(2)
C9 C1 C8 C14 84.1(2)
C6 C7 C8 C11 -179.20(18)
C6 C7 C8 C1 57.4(2)
C6 C7 C8 C14 -59.3(2)
C3 C2 C9 C10 0.2(3)
C3 C2 C9 C1 -177.1(2)
O1 C1 C9 C2 4.4(3)
C8 C1 C9 C2 -176.17(19)
O1 C1 C9 C10 -172.77(19)
C8 C1 C9 C10 6.6(3)
C4 C5 C10 C9 0.6(3)
C4 C5 C10 C6 179.8(2)
C2 C9 C10 C5 -0.9(3)
C1 C9 C10 C5 176.3(2)
C2 C9 C10 C6 179.83(19)
C1 C9 C10 C6 -3.0(3)
C7 C6 C10 C5 -152.0(2)
C7 C6 C10 C9 27.2(3)
C1 C8 C11 C13 107.8(2)
C7 C8 C11 C13 -15.3(3)
C14 C8 C11 C13 -135.3(2)
C1 C8 C11 C12 -73.5(2)
C7 C8 C11 C12 163.33(19)
C14 C8 C11 C12 43.4(3)
C11 C8 C14 O2 -124.3(2)
C1 C8 C14 O2 -5.1(3)
C7 C8 C14 O2 113.6(2)
C11 C8 C14 O3 55.7(2)
C1 C8 C14 O3 174.87(18)
C7 C8 C14 O3 -66.4(2)
O2 C14 O3 C15 2.7(3)
C8 C14 O3 C15 -177.31(18)
C18 C15 O3 C14 -65.6(3)
C16 C15 O3 C14 58.4(3)
C17 C15 O3 C14 176.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21197983
