#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/39/4023968.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_4023968
loop_
_publ_author_name
'Dhevalapally B. Ramachary'
'Mamillapalli Kishor'
_publ_section_title
;
 Organocatalytic Sequential One-Pot Double Cascade Asymmetric
 Synthesis of Wieland-Miescher Ketone Analogues from a
 Knoevenagel/Hydrogenation/Robinson Annulation Sequence:
 Scope and Applications of Organocatalytic Biomimetic Reductions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5056
_journal_page_last               5068
_journal_paper_doi               10.1021/jo070277i
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C13 H14 O2'
_chemical_formula_sum            'C13 H14 O2'
_chemical_formula_weight         202.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_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                 92.578(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.953(3)
_cell_length_b                   7.622(3)
_cell_length_c                   20.585(7)
_cell_measurement_reflns_used    1775
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.62
_cell_measurement_theta_min      2.85
_cell_volume                     1089.9(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5698
_diffrn_reflns_theta_full        26.09
_diffrn_reflns_theta_max         26.09
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0680
_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)+(0.0971P)²+0.3313P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1753
_refine_ls_wR_factor_ref         0.1966
_reflns_number_gt                1422
_reflns_number_total             2158
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070277isi20070209_033659.cif
_cod_data_source_block           dbr7aa
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023968
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0569(3) 0.6893(3) 0.05764(9) 0.0560(6) Uani 1 1 d . . .
O2 O 0.5879(3) 0.7271(4) 0.01048(13) 0.0864(8) Uani 1 1 d . . .
C1 C 0.0811(3) 0.7200(3) 0.01554(11) 0.0385(6) Uani 1 1 d . . .
C2 C 0.0167(4) 0.7764(4) -0.05122(12) 0.0473(7) Uani 1 1 d . . .
H2A H -0.0230 0.8983 -0.0501 0.057 Uiso 1 1 calc R . .
H2B H -0.0939 0.7069 -0.0658 0.057 Uiso 1 1 calc R . .
C3 C 0.1726(5) 0.7561(6) -0.09860(15) 0.0813(11) Uani 1 1 d . . .
H3A H 0.1793 0.6339 -0.1115 0.098 Uiso 1 1 calc R . .
H3B H 0.1387 0.8243 -0.1372 0.098 Uiso 1 1 calc R . .
C4 C 0.3630(4) 0.8116(5) -0.07310(15) 0.0721(9) Uani 1 1 d . . .
H4A H 0.3666 0.9388 -0.0718 0.087 Uiso 1 1 calc R . .
H4B H 0.4587 0.7731 -0.1029 0.087 Uiso 1 1 calc R . .
C5 C 0.4163(4) 0.7430(4) -0.00717(15) 0.0537(7) Uani 1 1 d . . .
C6 C 0.2672(3) 0.6995(3) 0.03621(11) 0.0410(6) Uani 1 1 d . . .
C7 C 0.3251(4) 0.6362(4) 0.10359(12) 0.0532(7) Uani 1 1 d . . .
H7A H 0.4323 0.5557 0.1007 0.064 Uiso 1 1 calc R . .
H7B H 0.2184 0.5714 0.1207 0.064 Uiso 1 1 calc R . .
C8 C 0.3823(4) 0.7808(3) 0.15104(11) 0.0457(6) Uani 1 1 d . . .
C9 C 0.5673(4) 0.7899(4) 0.17980(13) 0.0572(7) Uani 1 1 d . . .
H9 H 0.6589 0.7074 0.1689 0.069 Uiso 1 1 calc R . .
C10 C 0.6164(4) 0.9196(5) 0.22424(14) 0.0676(9) Uani 1 1 d . . .
H10 H 0.7405 0.9240 0.2430 0.081 Uiso 1 1 calc R . .
C11 C 0.4825(5) 1.0423(4) 0.24085(14) 0.0692(9) Uani 1 1 d . . .
H11 H 0.5148 1.1283 0.2715 0.083 Uiso 1 1 calc R . .
C12 C 0.2999(4) 1.0370(4) 0.21184(13) 0.0644(8) Uani 1 1 d . . .
H12 H 0.2096 1.1214 0.2222 0.077 Uiso 1 1 calc R . .
C13 C 0.2511(4) 0.9078(4) 0.16782(12) 0.0521(7) Uani 1 1 d . . .
H13 H 0.1273 0.9054 0.1488 0.063 Uiso 1 1 calc R . .
H1 H -0.171(5) 0.702(5) 0.0391(16) 0.084(11) Uiso 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 0.0033 0.0000 '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'
O O 0.0106 0.0000 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 111(2) . . ?
O1 C1 C6 118.6(2) . . ?
O1 C1 C2 116.9(2) . . ?
C6 C1 C2 124.6(2) . . ?
C1 C2 C3 112.0(2) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 113.9(3) . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 C5 114.2(3) . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
O2 C5 C6 120.5(3) . . ?
O2 C5 C4 120.0(3) . . ?
C6 C5 C4 119.5(2) . . ?
C1 C6 C5 119.0(2) . . ?
C1 C6 C7 122.6(2) . . ?
C5 C6 C7 118.4(2) . . ?
C6 C7 C8 114.4(2) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C13 C8 C9 117.7(2) . . ?
C13 C8 C7 120.9(2) . . ?
C9 C8 C7 121.4(2) . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 121.4(3) . . ?
C12 C13 H13 119.3 . . ?
C8 C13 H13 119.3 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.343(3) . ?
O1 H1 0.87(4) . ?
O2 C5 1.238(3) . ?
C1 C6 1.353(3) . ?
C1 C2 1.489(3) . ?
C2 C3 1.499(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.465(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.486(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.437(4) . ?
C6 C7 1.506(3) . ?
C7 C8 1.514(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C13 1.385(4) . ?
C8 C9 1.393(4) . ?
C9 C10 1.379(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658817
