#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/31/1503170.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_1503170
loop_
_publ_author_name
'Yang, Luo'
'Lei, Chuan-Hu'
'Wang, De-Xian'
'Huang, Zhi-Tang'
'Wang, Mei-Xiang'
_publ_section_title
;
 Highly efficient and expedient synthesis of
 5-hydroxy-1H-pyrrol-2-(5H)-ones from FeCl3-catalyzed tandem
 intramolecular enaminic addition of tertiary enamides to ketones and
 1,3-hydroxy rearrangement.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3918
_journal_page_last               3921
_journal_paper_doi               10.1021/ol101607z
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C24 H21 N O2'
_chemical_formula_weight         355.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 101.57(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5467(17)
_cell_length_b                   10.490(2)
_cell_length_c                   21.228(4)
_cell_measurement_reflns_used    5493
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.96
_cell_volume                     1864.5(7)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Raxis Rapid IP'
_diffrn_measurement_method       oscillation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5493
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_correction_T_min  0.9740
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   abscor
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.0085(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0535
_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)+(0.0726P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1373
_reflns_number_gt                2572
_reflns_number_total             3272
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101607z_si_002.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1864.6(6)
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               1503170
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.16964(15) 0.91413(13) 0.17686(6) 0.0434(4) Uani 1 1 d .
O2 O 0.04978(16) 0.64884(13) 0.15790(6) 0.0436(4) Uani 1 1 d .
N1 N 0.16224(17) 0.86344(14) 0.28183(7) 0.0321(4) Uani 1 1 d .
C1 C 0.1207(2) 0.84959(17) 0.21645(8) 0.0325(4) Uani 1 1 d .
C4 C 0.0965(2) 0.76026(17) 0.31245(8) 0.0320(4) Uani 1 1 d .
C7 C -0.1624(2) 0.78457(17) 0.17162(8) 0.0336(4) Uani 1 1 d .
C19 C 0.4348(2) 0.87963(19) 0.34965(9) 0.0373(5) Uani 1 1 d .
C18 C 0.1051(2) 0.8525(2) 0.42262(9) 0.0414(5) Uani 1 1 d .
H18A H 0.0877 0.9338 0.4052 0.050 Uiso 1 1 calc R
C2 C 0.0034(2) 0.73551(18) 0.20254(9) 0.0339(4) Uani 1 1 d .
C5 C 0.2903(2) 0.94863(18) 0.31256(9) 0.0380(5) Uani 1 1 d .
H5A H 0.2493 1.0050 0.3416 0.046 Uiso 1 1 calc R
H5B H 0.3230 1.0009 0.2798 0.046 Uiso 1 1 calc R
C3 C 0.0105(2) 0.68405(18) 0.26892(9) 0.0371(5) Uani 1 1 d .
H3A H -0.0385 0.6092 0.2783 0.045 Uiso 1 1 calc R
C13 C 0.1190(2) 0.74966(18) 0.38302(8) 0.0334(5) Uani 1 1 d .
C12 C -0.2173(2) 0.7803(2) 0.10594(10) 0.0460(5) Uani 1 1 d .
H12A H -0.1530 0.7460 0.0797 0.055 Uiso 1 1 calc R
C8 C -0.2603(3) 0.8375(2) 0.20882(10) 0.0524(6) Uani 1 1 d .
H8A H -0.2259 0.8406 0.2532 0.063 Uiso 1 1 calc R
C14 C 0.1459(3) 0.6294(2) 0.41043(9) 0.0471(5) Uani 1 1 d .
H14A H 0.1566 0.5595 0.3847 0.056 Uiso 1 1 calc R
C20 C 0.4921(2) 0.7691(2) 0.32699(11) 0.0504(6) Uani 1 1 d .
H20A H 0.4385 0.7341 0.2884 0.061 Uiso 1 1 calc R
C17 C 0.1170(3) 0.8346(2) 0.48779(10) 0.0492(6) Uani 1 1 d .
H17A H 0.1074 0.9041 0.5140 0.059 Uiso 1 1 calc R
C24 C 0.5158(2) 0.9288(2) 0.40766(10) 0.0491(6) Uani 1 1 d .
H24A H 0.4790 1.0027 0.4241 0.059 Uiso 1 1 calc R
C11 C -0.3671(3) 0.8266(2) 0.07879(10) 0.0567(6) Uani 1 1 d .
H11A H -0.4033 0.8224 0.0345 0.068 Uiso 1 1 calc R
C10 C -0.4623(3) 0.8786(2) 0.11677(12) 0.0584(6) Uani 1 1 d .
H10A H -0.5635 0.9087 0.0984 0.070 Uiso 1 1 calc R
C16 C 0.1429(3) 0.7150(2) 0.51439(10) 0.0531(6) Uani 1 1 d .
H16A H 0.1508 0.7035 0.5584 0.064 Uiso 1 1 calc R
C9 C -0.4082(3) 0.8860(3) 0.18154(11) 0.0606(7) Uani 1 1 d .
H9A H -0.4711 0.9238 0.2074 0.073 Uiso 1 1 calc R
C15 C 0.1568(3) 0.6132(2) 0.47579(10) 0.0564(6) Uani 1 1 d .
H15A H 0.1738 0.5322 0.4936 0.068 Uiso 1 1 calc R
C21 C 0.6278(3) 0.7095(3) 0.36067(12) 0.0602(7) Uani 1 1 d .
H21A H 0.6653 0.6357 0.3445 0.072 Uiso 1 1 calc R
C6 C 0.2095(3) 0.6041(2) 0.17549(10) 0.0574(6) Uani 1 1 d .
H6A H 0.2314 0.5468 0.1431 0.086 Uiso 1 1 calc R
H6B H 0.2233 0.5602 0.2159 0.086 Uiso 1 1 calc R
H6C H 0.2816 0.6751 0.1794 0.086 Uiso 1 1 calc R
C23 C 0.6511(3) 0.8685(3) 0.44121(11) 0.0618(7) Uani 1 1 d .
H23A H 0.7050 0.9022 0.4801 0.074 Uiso 1 1 calc R
C22 C 0.7063(3) 0.7594(3) 0.41757(12) 0.0609(7) Uani 1 1 d .
H22A H 0.7974 0.7194 0.4404 0.073 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
C6 O2 C2 114.60(14)
C1 N1 C4 109.51(14)
C1 N1 C5 122.39(15)
C4 N1 C5 125.85(14)
O1 C1 N1 125.87(17)
O1 C1 C2 126.61(16)
N1 C1 C2 107.50(15)
C3 C4 N1 110.59(16)
C3 C4 C13 127.06(17)
N1 C4 C13 122.27(15)
C8 C7 C12 118.01(18)
C8 C7 C2 120.51(16)
C12 C7 C2 121.46(17)
C20 C19 C24 118.24(19)
C20 C19 C5 122.05(17)
C24 C19 C5 119.70(19)
C17 C18 C13 120.29(19)
C17 C18 H18A 119.9
C13 C18 H18A 119.9
O2 C2 C3 115.54(15)
O2 C2 C7 106.68(13)
C3 C2 C7 112.61(16)
O2 C2 C1 111.30(15)
C3 C2 C1 101.32(14)
C7 C2 C1 109.31(14)
N1 C5 C19 113.62(15)
N1 C5 H5A 108.8
C19 C5 H5A 108.8
N1 C5 H5B 108.8
C19 C5 H5B 108.8
H5A C5 H5B 107.7
C4 C3 C2 110.49(17)
C4 C3 H3A 124.8
C2 C3 H3A 124.8
C18 C13 C14 118.63(18)
C18 C13 C4 123.17(17)
C14 C13 C4 118.08(17)
C7 C12 C11 120.6(2)
C7 C12 H12A 119.7
C11 C12 H12A 119.7
C7 C8 C9 121.30(19)
C7 C8 H8A 119.4
C9 C8 H8A 119.4
C15 C14 C13 120.3(2)
C15 C14 H14A 119.9
C13 C14 H14A 119.9
C19 C20 C21 121.2(2)
C19 C20 H20A 119.4
C21 C20 H20A 119.4
C16 C17 C18 120.6(2)
C16 C17 H17A 119.7
C18 C17 H17A 119.7
C23 C24 C19 120.3(2)
C23 C24 H24A 119.9
C19 C24 H24A 119.9
C10 C11 C12 120.3(2)
C10 C11 H11A 119.9
C12 C11 H11A 119.9
C9 C10 C11 119.8(2)
C9 C10 H10A 120.1
C11 C10 H10A 120.1
C15 C16 C17 119.5(2)
C15 C16 H16A 120.2
C17 C16 H16A 120.2
C10 C9 C8 120.0(2)
C10 C9 H9A 120.0
C8 C9 H9A 120.0
C16 C15 C14 120.7(2)
C16 C15 H15A 119.7
C14 C15 H15A 119.7
C22 C21 C20 119.9(2)
C22 C21 H21A 120.1
C20 C21 H21A 120.1
O2 C6 H6A 109.5
O2 C6 H6B 109.5
H6A C6 H6B 109.5
O2 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C22 C23 C24 120.5(2)
C22 C23 H23A 119.8
C24 C23 H23A 119.8
C21 C22 C23 120.0(2)
C21 C22 H22A 120.0
C23 C22 H22A 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.217(2)
O2 C6 1.420(2)
O2 C2 1.426(2)
N1 C1 1.370(2)
N1 C4 1.434(2)
N1 C5 1.462(2)
C1 C2 1.551(3)
C4 C3 1.327(2)
C4 C13 1.476(3)
C7 C8 1.378(3)
C7 C12 1.380(3)
C7 C2 1.527(3)
C19 C20 1.382(3)
C19 C24 1.386(3)
C19 C5 1.509(3)
C18 C17 1.379(3)
C18 C13 1.387(3)
C18 H18A 0.9300
C2 C3 1.499(3)
C5 H5A 0.9700
C5 H5B 0.9700
C3 H3A 0.9300
C13 C14 1.389(3)
C12 C11 1.382(3)
C12 H12A 0.9300
C8 C9 1.378(3)
C8 H8A 0.9300
C14 C15 1.382(3)
C14 H14A 0.9300
C20 C21 1.383(3)
C20 H20A 0.9300
C17 C16 1.376(3)
C17 H17A 0.9300
C24 C23 1.384(3)
C24 H24A 0.9300
C11 C10 1.368(3)
C11 H11A 0.9300
C10 C9 1.362(3)
C10 H10A 0.9300
C16 C15 1.365(3)
C16 H16A 0.9300
C9 H9A 0.9300
C15 H15A 0.9300
C21 C22 1.363(3)
C21 H21A 0.9300
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C23 C22 1.371(4)
C23 H23A 0.9300
C22 H22A 0.9300
