#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/59/1515979.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_1515979
loop_
_publ_author_name
'Jhuo, Dai-Huei'
'Hong, Bor-Cherng'
'Chang, Chun-Wei'
'Lee, Gene-Hsiang'
_publ_section_title
;
 One-pot organocatalytic enantioselective Michael-Michael-aldol-Henry
 reaction cascade. A facile entry to the steroid system with six
 contiguous stereogenic centers.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2724
_journal_page_last               2727
_journal_paper_doi               10.1021/ol501011t
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H19 N O4'
_chemical_formula_weight         265.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3853(2)
_cell_length_b                   10.1226(2)
_cell_length_c                   17.8638(3)
_cell_measurement_reflns_used    13945
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.28
_cell_volume                     1335.47(5)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'NONIUS COLLECT'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'NONIUS KappaCCD'
_diffrn_measurement_method       'ω 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  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13945
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.133
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(1)
_refine_ls_extinction_coef       0.100(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0395
_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)+(0.0689P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1045
_reflns_number_gt                2613
_reflns_number_total             3054
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501011t_si_003.cif
_cod_data_source_block           ic15968
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1515977--1515979.cif.
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1515979
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
O1 O 0.93796(15) 0.89228(12) 0.54324(5) 0.0484(3) Uani 1 1 d .
O2 O 0.87850(16) 1.01770(11) 0.10611(6) 0.0492(3) Uani 1 1 d .
H2 H 0.7910 1.0648 0.0923 0.074 Uiso 1 1 calc R
O3 O 0.77538(17) 0.60830(11) 0.22124(6) 0.0524(3) Uani 1 1 d .
O4 O 0.59656(18) 0.67433(12) 0.13477(7) 0.0614(4) Uani 1 1 d .
N1 N 0.71868(17) 0.69453(12) 0.17992(7) 0.0398(3) Uani 1 1 d .
C1 C 0.93856(19) 0.87701(15) 0.47502(7) 0.0370(3) Uani 1 1 d .
C2 C 0.76651(19) 0.85329(15) 0.43134(8) 0.0392(4) Uani 1 1 d .
H2A H 0.6672 0.9054 0.4540 0.047 Uiso 1 1 calc R
H2B H 0.7335 0.7587 0.4349 0.047 Uiso 1 1 calc R
C3 C 0.78516(17) 0.89099(14) 0.34939(7) 0.0319(3) Uani 1 1 d .
H3 H 0.8165 0.9870 0.3475 0.038 Uiso 1 1 calc R
C4 C 0.61073(17) 0.87230(15) 0.30474(8) 0.0375(3) Uani 1 1 d .
H4A H 0.5129 0.9261 0.3273 0.045 Uiso 1 1 calc R
H4B H 0.5735 0.7784 0.3067 0.045 Uiso 1 1 calc R
C5 C 0.63888(19) 0.91384(15) 0.22330(8) 0.0382(3) Uani 1 1 d .
H5A H 0.6675 1.0093 0.2215 0.046 Uiso 1 1 calc R
H5B H 0.5251 0.8995 0.1951 0.046 Uiso 1 1 calc R
C6 C 0.79181(18) 0.83644(14) 0.18571(8) 0.0340(3) Uani 1 1 d .
C7 C 0.8271(2) 0.88210(17) 0.10383(8) 0.0421(4) Uani 1 1 d .
H7 H 0.7136 0.8723 0.0738 0.050 Uiso 1 1 calc R
C8 C 0.9773(2) 0.8025(2) 0.06793(8) 0.0521(4) Uani 1 1 d .
H8A H 0.9990 0.8357 0.0166 0.063 Uiso 1 1 calc R
H8B H 0.9393 0.7089 0.0642 0.063 Uiso 1 1 calc R
C9 C 1.1527(2) 0.8109(2) 0.11273(8) 0.0542(5) Uani 1 1 d .
H9A H 1.1982 0.9029 0.1119 0.065 Uiso 1 1 calc R
H9B H 1.2455 0.7537 0.0893 0.065 Uiso 1 1 calc R
C10 C 1.1229(2) 0.76774(17) 0.19382(8) 0.0429(4) Uani 1 1 d .
H10A H 1.2360 0.7812 0.2225 0.051 Uiso 1 1 calc R
H10B H 1.0937 0.6723 0.1949 0.051 Uiso 1 1 calc R
C11 C 0.96909(18) 0.84532(14) 0.23105(7) 0.0305(3) Uani 1 1 d .
H11 H 1.0065 0.9402 0.2286 0.037 Uiso 1 1 calc R
C12 C 0.94454(16) 0.81478(13) 0.31512(7) 0.0294(3) Uani 1 1 d .
H12 H 0.9187 0.7182 0.3203 0.035 Uiso 1 1 calc R
C13 C 1.11117(19) 0.84531(14) 0.35992(7) 0.0346(3) Uani 1 1 d .
H13 H 1.2252 0.8419 0.3354 0.042 Uiso 1 1 calc R
C14 C 1.10747(19) 0.87706(16) 0.43261(8) 0.0380(3) Uani 1 1 d .
H14 H 1.2171 0.9001 0.4571 0.046 Uiso 1 1 calc R
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
O3 N1 O4 122.13(13)
O3 N1 C6 120.54(11)
O4 N1 C6 117.25(12)
O1 C1 C14 121.20(13)
O1 C1 C2 121.97(13)
C14 C1 C2 116.80(11)
C1 C2 C3 112.44(11)
C2 C3 C4 113.31(11)
C2 C3 C12 109.12(11)
C4 C3 C12 112.11(11)
C3 C4 C5 110.39(11)
C4 C5 C6 112.17(11)
C5 C6 N1 104.39(11)
C5 C6 C11 111.49(11)
N1 C6 C11 112.82(11)
C5 C6 C7 112.60(12)
N1 C6 C7 105.85(11)
C11 C6 C7 109.52(11)
O2 C7 C8 109.27(14)
O2 C7 C6 107.70(11)
C8 C7 C6 111.28(13)
C7 C8 C9 111.73(13)
C8 C9 C10 111.01(14)
C9 C10 C11 111.81(13)
C10 C11 C6 111.79(11)
C10 C11 C12 113.99(10)
C6 C11 C12 113.55(11)
C13 C12 C3 108.23(10)
C13 C12 C11 112.41(10)
C3 C12 C11 112.17(10)
C14 C13 C12 123.40(13)
C13 C14 C1 121.41(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2285(17)
O2 C7 1.425(2)
O3 N1 1.2174(17)
O4 N1 1.2271(16)
N1 C6 1.5381(18)
C1 C14 1.460(2)
C1 C2 1.510(2)
C2 C3 1.5192(19)
C3 C4 1.5269(18)
C3 C12 1.5348(17)
C4 C5 1.529(2)
C5 C6 1.530(2)
C6 C11 1.5422(18)
C6 C7 1.556(2)
C7 C8 1.514(2)
C8 C9 1.525(2)
C9 C10 1.529(2)
C10 C11 1.533(2)
C11 C12 1.5439(17)
C12 C13 1.5001(19)
C13 C14 1.338(2)
