#------------------------------------------------------------------------------
#$Date: 2019-11-24 16:26:42 +0100 (dom 24 de nov de 2019) $
#$Revision: 238821 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/55/1555510.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_1555510
loop_
_publ_author_name
'Raja, Arun'
'Hong, Bor-Cherng'
'Liao, Ju-Hsiou'
'Lee, Gene-Hsiang'
_publ_section_title
;
 Organocatalytic Enantioselective Michael-Michael-Henry Reaction Cascade.
 An Entry to Highly Functionalized Hajos-Parrish-Type Ketones with Five to
 Six Contiguous Stereogenic Centers and Two Quaternary Carbons.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1760
_journal_page_last               1763
_journal_paper_doi               10.1021/acs.orglett.6b00459
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H23 N O5'
_chemical_formula_sum            'C23 H23 N O5'
_chemical_formula_weight         393.42
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 97.222(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.5186(17)
_cell_length_b                   6.7973(7)
_cell_length_c                   17.4934(18)
_cell_measurement_reflns_used    584
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.529
_cell_measurement_theta_min      2.28
_cell_volume                     1948.6(3)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    Ortep-3
_computing_publication_material  'Wingx publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       'phi-omega scan'
_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  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18547
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.60
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.180
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0595
_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)+(0.0845P)²+1.4870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1630
_refine_ls_wR_factor_ref         0.1719
_reflns_number_gt                3294
_reflns_number_total             3629
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00459_si_004.cif
_cod_data_source_block           ar04
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Empirical' was
changed to 'empirical' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1555510
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.94999(11) -0.2366(3) -0.00037(11) 0.0409(5) Uani 1 1 d .
O2 O 0.80106(10) -0.1391(2) 0.12543(9) 0.0273(4) Uani 1 1 d .
H2 H 0.836(2) -0.250(5) 0.1414(19) 0.059(10) Uiso 1 1 d .
O3 O 0.89518(11) 0.5238(2) 0.15860(11) 0.0375(4) Uani 1 1 d .
O4 O 0.69779(11) 0.5975(3) -0.04434(10) 0.0380(4) Uani 1 1 d .
O5 O 0.65244(10) 0.3107(3) -0.08297(10) 0.0366(4) Uani 1 1 d .
N1 N 0.70189(11) 0.4170(3) -0.04529(10) 0.0270(4) Uani 1 1 d .
C1 C 0.78162(15) -0.0058(4) -0.16024(13) 0.0324(5) Uani 1 1 d .
H1 H 0.7431 -0.0994 -0.1468 0.039 Uiso 1 1 calc R
C2 C 0.80555(16) -0.0090(4) -0.23367(14) 0.0372(6) Uani 1 1 d .
H2A H 0.7844 -0.1065 -0.2696 0.045 Uiso 1 1 calc R
C3 C 0.85982(14) 0.1287(4) -0.25428(13) 0.0339(6) Uani 1 1 d .
H3 H 0.8757 0.1268 -0.3046 0.041 Uiso 1 1 calc R
C4 C 0.89143(13) 0.2703(4) -0.20178(13) 0.0298(5) Uani 1 1 d .
H4 H 0.9282 0.3668 -0.2163 0.036 Uiso 1 1 calc R
C5 C 0.86899(13) 0.2705(3) -0.12785(12) 0.0254(5) Uani 1 1 d .
H5 H 0.8917 0.3656 -0.0915 0.031 Uiso 1 1 calc R
C6 C 0.81353(12) 0.1329(3) -0.10640(12) 0.0236(5) Uani 1 1 d .
C7 C 0.79195(12) 0.1230(3) -0.02410(12) 0.0218(5) Uani 1 1 d .
H7 H 0.7441 0.0336 -0.0227 0.026 Uiso 1 1 calc R
C8 C 0.86597(12) 0.0391(3) 0.02876(12) 0.0220(5) Uani 1 1 d .
H8 H 0.9144 0.1249 0.0245 0.026 Uiso 1 1 calc R
C9 C 0.88351(14) -0.1652(3) -0.00025(12) 0.0268(5) Uani 1 1 d .
H9 H 0.8379 -0.2432 -0.0200 0.032 Uiso 1 1 calc R
C10 C 0.85306(13) 0.0233(3) 0.11508(12) 0.0228(5) Uani 1 1 d .
C11 C 0.93679(14) 0.0050(3) 0.16430(13) 0.0287(5) Uani 1 1 d .
H11A H 0.9312 -0.0565 0.2147 0.034 Uiso 1 1 calc R
H11B H 0.9744 -0.0756 0.1375 0.034 Uiso 1 1 calc R
C12 C 0.96855(14) 0.2173(4) 0.17526(14) 0.0305(5) Uani 1 1 d .
H12A H 0.9948 0.2381 0.2287 0.037 Uiso 1 1 calc R
H12B H 1.0088 0.2463 0.1393 0.037 Uiso 1 1 calc R
C13 C 0.89415(13) 0.3463(3) 0.15817(12) 0.0265(5) Uani 1 1 d .
C14 C 0.81716(13) 0.2180(3) 0.14320(11) 0.0215(5) Uani 1 1 d .
C15 C 0.79110(15) 0.1915(4) 0.22437(13) 0.0302(5) Uani 1 1 d .
H15A H 0.8359 0.1313 0.2585 0.045 Uiso 1 1 calc R
H15B H 0.7430 0.1062 0.2211 0.045 Uiso 1 1 calc R
H15C H 0.7780 0.3201 0.2449 0.045 Uiso 1 1 calc R
C16 C 0.74883(12) 0.3231(3) 0.08964(12) 0.0228(5) Uani 1 1 d .
H16 H 0.7513 0.4639 0.1063 0.027 Uiso 1 1 calc R
C17 C 0.77184(12) 0.3236(3) 0.00643(12) 0.0226(5) Uani 1 1 d .
H17 H 0.8209 0.4095 0.0058 0.027 Uiso 1 1 calc R
C18 C 0.66087(13) 0.2581(3) 0.09398(12) 0.0265(5) Uani 1 1 d .
C19 C 0.60345(14) 0.4065(4) 0.09757(13) 0.0318(5) Uani 1 1 d .
H19 H 0.6204 0.5401 0.0988 0.038 Uiso 1 1 calc R
C20 C 0.52149(15) 0.3620(4) 0.09936(15) 0.0416(7) Uani 1 1 d .
H20 H 0.4830 0.4650 0.1016 0.050 Uiso 1 1 calc R
C21 C 0.49617(15) 0.1705(5) 0.09791(16) 0.0440(7) Uani 1 1 d .
H21 H 0.4402 0.1404 0.0993 0.053 Uiso 1 1 calc R
C22 C 0.55211(16) 0.0211(4) 0.09449(16) 0.0408(6) Uani 1 1 d .
H22 H 0.5345 -0.1120 0.0939 0.049 Uiso 1 1 calc R
C23 C 0.63405(14) 0.0638(4) 0.09193(14) 0.0335(5) Uani 1 1 d .
H23 H 0.6719 -0.0401 0.0888 0.040 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
O5 N1 O4 124.34(19)
O5 N1 C17 118.90(18)
O4 N1 C17 116.72(18)
C6 C1 C2 120.6(2)
C3 C2 C1 120.1(2)
C2 C3 C4 120.2(2)
C3 C4 C5 119.7(2)
C4 C5 C6 120.7(2)
C1 C6 C5 118.7(2)
C1 C6 C7 119.73(19)
C5 C6 C7 121.49(19)
C17 C7 C6 112.34(17)
C17 C7 C8 108.23(17)
C6 C7 C8 108.60(16)
C9 C8 C7 107.88(17)
C9 C8 C10 108.45(17)
C7 C8 C10 114.30(16)
O1 C9 C8 125.7(2)
O2 C10 C11 112.34(17)
O2 C10 C8 109.61(16)
C11 C10 C8 108.99(17)
O2 C10 C14 111.07(16)
C11 C10 C14 104.08(17)
C8 C10 C14 110.65(16)
C12 C11 C10 105.19(17)
C13 C12 C11 105.29(18)
O3 C13 C12 124.7(2)
O3 C13 C14 125.4(2)
C12 C13 C14 109.89(18)
C13 C14 C15 103.29(17)
C13 C14 C16 111.50(17)
C15 C14 C16 110.13(17)
C13 C14 C10 101.32(16)
C15 C14 C10 110.64(17)
C16 C14 C10 118.62(17)
C18 C16 C14 117.50(18)
C18 C16 C17 113.20(17)
C14 C16 C17 108.87(16)
N1 C17 C7 110.55(17)
N1 C17 C16 107.65(16)
C7 C17 C16 114.78(17)
C19 C18 C23 118.2(2)
C19 C18 C16 116.8(2)
C23 C18 C16 125.0(2)
C18 C19 C20 120.9(2)
C21 C20 C19 120.2(2)
C20 C21 C22 119.8(2)
C21 C22 C23 120.5(3)
C22 C23 C18 120.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.201(3)
O2 C10 1.424(3)
O3 C13 1.207(3)
O4 N1 1.229(3)
O5 N1 1.220(3)
N1 C17 1.515(3)
C1 C6 1.389(3)
C1 C2 1.391(3)
C2 C3 1.375(4)
C3 C4 1.386(4)
C4 C5 1.389(3)
C5 C6 1.394(3)
C6 C7 1.527(3)
C7 C17 1.516(3)
C7 C8 1.546(3)
C8 C9 1.519(3)
C8 C10 1.555(3)
C10 C11 1.540(3)
C10 C14 1.555(3)
C11 C12 1.539(3)
C12 C13 1.509(3)
C13 C14 1.537(3)
C14 C15 1.545(3)
C14 C16 1.548(3)
C16 C18 1.530(3)
C16 C17 1.550(3)
C18 C19 1.391(3)
C18 C23 1.392(3)
C19 C20 1.392(4)
C20 C21 1.366(4)
C21 C22 1.380(4)
C22 C23 1.391(3)
