#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/25/1502503.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_1502503
loop_
_publ_author_name
'Lv, Hui'
'Mo, Junming'
'Fang, Xinqiang'
'Chi, Yonggui Robin'
_publ_section_title
;
 Formal Diels-Alder reactions of chalcones and formylcyclopropanes
 catalyzed by chiral N-heterocyclic carbenes.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5366
_journal_page_last               5369
_journal_paper_doi               10.1021/ol202250s
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C27 H26 O4'
_chemical_formula_sum            'C27 H26 O4'
_chemical_formula_weight         414.48
_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                   10.1002(2)
_cell_length_b                   13.2118(3)
_cell_length_c                   16.2598(3)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      33.77
_cell_measurement_theta_min      2.51
_cell_volume                     2169.74(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            41929
_diffrn_reflns_theta_full        33.87
_diffrn_reflns_theta_max         33.87
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9719
_exptl_absorpt_correction_T_min  0.9671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0717P)²+0.1658P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                4410
_reflns_number_total             4846
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202250s_si_002.cif
_cod_data_source_block           cyg21s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1502503
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
C1 C 0.39806(12) 0.97701(9) 0.99190(7) 0.01187(19) Uani 1 1 d .
C2 C 0.43671(12) 0.89884(9) 0.92467(6) 0.01130(19) Uani 1 1 d .
H2 H 0.5354 0.8961 0.9207 0.014 Uiso 1 1 calc R
C3 C 0.38503(13) 0.79284(9) 0.94589(7) 0.0133(2) Uani 1 1 d .
H3A H 0.4123 0.7443 0.9027 0.016 Uiso 1 1 calc R
H3B H 0.2871 0.7938 0.9481 0.016 Uiso 1 1 calc R
C4 C 0.44063(12) 0.75913(9) 1.02935(6) 0.01153(18) Uani 1 1 d .
H4 H 0.5394 0.7570 1.0259 0.014 Uiso 1 1 calc R
C5 C 0.40008(12) 0.83411(9) 1.09791(6) 0.01167(19) Uani 1 1 d .
H5 H 0.3012 0.8359 1.1004 0.014 Uiso 1 1 calc R
C6 C 0.44902(13) 0.94082(9) 1.07572(7) 0.01281(19) Uani 1 1 d .
H6A H 0.4196 0.9889 1.1187 0.015 Uiso 1 1 calc R
H6B H 0.5470 0.9410 1.0751 0.015 Uiso 1 1 calc R
C7 C 0.45872(12) 1.07933(9) 0.96903(7) 0.01268(19) Uani 1 1 d .
C8 C 0.38018(14) 1.15984(10) 0.94365(8) 0.0188(2) Uani 1 1 d .
H8 H 0.2867 1.1521 0.9412 0.023 Uiso 1 1 calc R
C9 C 0.43774(17) 1.25203(10) 0.92166(9) 0.0245(3) Uani 1 1 d .
H9 H 0.3831 1.3066 0.9044 0.029 Uiso 1 1 calc R
C10 C 0.57386(17) 1.26478(10) 0.92477(9) 0.0232(3) Uani 1 1 d .
H10 H 0.6125 1.3281 0.9109 0.028 Uiso 1 1 calc R
C11 C 0.65315(15) 1.18389(10) 0.94832(8) 0.0195(2) Uani 1 1 d .
H11 H 0.7467 1.1915 0.9496 0.023 Uiso 1 1 calc R
C12 C 0.59625(13) 1.09215(9) 0.96998(8) 0.0153(2) Uani 1 1 d .
H12 H 0.6514 1.0372 0.9857 0.018 Uiso 1 1 calc R
C13 C 0.38142(12) 0.93421(9) 0.84244(7) 0.0136(2) Uani 1 1 d .
C14 C 0.47053(12) 0.96290(9) 0.77316(7) 0.01242(19) Uani 1 1 d .
C15 C 0.41170(14) 1.00255(10) 0.70196(7) 0.0166(2) Uani 1 1 d .
H15 H 0.3182 1.0092 0.6990 0.020 Uiso 1 1 calc R
C16 C 0.48924(15) 1.03206(10) 0.63587(7) 0.0191(2) Uani 1 1 d .
H16 H 0.4490 1.0588 0.5877 0.023 Uiso 1 1 calc R
C17 C 0.62625(14) 1.02240(10) 0.64023(7) 0.0181(2) Uani 1 1 d .
H17 H 0.6796 1.0433 0.5952 0.022 Uiso 1 1 calc R
C18 C 0.68513(13) 0.98241(11) 0.71000(8) 0.0186(2) Uani 1 1 d .
H18 H 0.7786 0.9753 0.7124 0.022 Uiso 1 1 calc R
C19 C 0.60786(13) 0.95271(10) 0.77652(7) 0.0165(2) Uani 1 1 d .
H19 H 0.6486 0.9255 0.8243 0.020 Uiso 1 1 calc R
C20 C 0.39043(12) 0.65499(9) 1.05124(7) 0.01242(19) Uani 1 1 d .
C21 C 0.45110(15) 0.49312(10) 1.10248(9) 0.0224(3) Uani 1 1 d .
H21A H 0.4376 0.4496 1.0544 0.034 Uiso 1 1 calc R
H21B H 0.3689 0.4968 1.1344 0.034 Uiso 1 1 calc R
H21C H 0.5218 0.4650 1.1369 0.034 Uiso 1 1 calc R
C22 C 0.45093(13) 0.80040(9) 1.18116(7) 0.0136(2) Uani 1 1 d .
C23 C 0.58665(14) 0.79492(10) 1.19677(7) 0.0177(2) Uani 1 1 d .
H23 H 0.6476 0.8153 1.1555 0.021 Uiso 1 1 calc R
C24 C 0.63382(16) 0.76007(11) 1.27196(8) 0.0230(3) Uani 1 1 d .
H24 H 0.7264 0.7568 1.2818 0.028 Uiso 1 1 calc R
C25 C 0.54517(18) 0.73000(11) 1.33282(8) 0.0246(3) Uani 1 1 d .
H25 H 0.5771 0.7055 1.3840 0.029 Uiso 1 1 calc R
C26 C 0.41047(18) 0.73599(12) 1.31837(8) 0.0245(3) Uani 1 1 d .
H26 H 0.3498 0.7162 1.3600 0.029 Uiso 1 1 calc R
C27 C 0.36315(15) 0.77095(10) 1.24280(7) 0.0196(2) Uani 1 1 d .
H27 H 0.2705 0.7747 1.2334 0.024 Uiso 1 1 calc R
O1 O 0.25791(9) 0.98410(8) 0.99993(6) 0.01638(17) Uani 1 1 d .
H1 H 0.2220 0.9689 0.9550 0.025 Uiso 1 1 calc R
O2 O 0.26103(10) 0.94119(9) 0.83470(6) 0.0214(2) Uani 1 1 d .
O3 O 0.27487(10) 0.63009(7) 1.04818(6) 0.01799(18) Uani 1 1 d .
O4 O 0.48797(10) 0.59368(7) 1.07551(6) 0.01685(18) 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 0.0033 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
O1 C1 C7 111.23(10)
O1 C1 C6 105.83(9)
C7 C1 C6 110.92(9)
O1 C1 C2 110.96(9)
C7 C1 C2 108.40(9)
C6 C1 C2 109.50(9)
C13 C2 C3 110.67(9)
C13 C2 C1 108.77(9)
C3 C2 C1 111.29(9)
C13 C2 H2 108.7
C3 C2 H2 108.7
C1 C2 H2 108.7
C2 C3 C4 109.84(9)
C2 C3 H3A 109.7
C4 C3 H3A 109.7
C2 C3 H3B 109.7
C4 C3 H3B 109.7
H3A C3 H3B 108.2
C20 C4 C3 110.50(10)
C20 C4 C5 108.97(9)
C3 C4 C5 110.77(9)
C20 C4 H4 108.9
C3 C4 H4 108.9
C5 C4 H4 108.9
C22 C5 C6 111.74(9)
C22 C5 C4 111.47(9)
C6 C5 C4 109.47(9)
C22 C5 H5 108.0
C6 C5 H5 108.0
C4 C5 H5 108.0
C1 C6 C5 112.75(9)
C1 C6 H6A 109.0
C5 C6 H6A 109.0
C1 C6 H6B 109.0
C5 C6 H6B 109.0
H6A C6 H6B 107.8
C8 C7 C12 118.51(11)
C8 C7 C1 121.32(11)
C12 C7 C1 120.11(10)
C7 C8 C9 120.40(13)
C7 C8 H8 119.8
C9 C8 H8 119.8
C10 C9 C8 120.64(13)
C10 C9 H9 119.7
C8 C9 H9 119.7
C9 C10 C11 119.24(13)
C9 C10 H10 120.4
C11 C10 H10 120.4
C12 C11 C10 120.23(13)
C12 C11 H11 119.9
C10 C11 H11 119.9
C11 C12 C7 120.94(12)
C11 C12 H12 119.5
C7 C12 H12 119.5
O2 C13 C14 120.14(11)
O2 C13 C2 118.50(11)
C14 C13 C2 121.34(10)
C19 C14 C15 119.31(11)
C19 C14 C13 123.11(10)
C15 C14 C13 117.57(11)
C16 C15 C14 120.38(12)
C16 C15 H15 119.8
C14 C15 H15 119.8
C15 C16 C17 119.79(11)
C15 C16 H16 120.1
C17 C16 H16 120.1
C18 C17 C16 120.23(12)
C18 C17 H17 119.9
C16 C17 H17 119.9
C17 C18 C19 120.24(12)
C17 C18 H18 119.9
C19 C18 H18 119.9
C18 C19 C14 120.04(11)
C18 C19 H19 120.0
C14 C19 H19 120.0
O3 C20 O4 123.87(11)
O3 C20 C4 124.11(11)
O4 C20 C4 112.02(10)
O4 C21 H21A 109.5
O4 C21 H21B 109.5
H21A C21 H21B 109.5
O4 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C27 C22 C23 118.66(11)
C27 C22 C5 120.60(12)
C23 C22 C5 120.71(10)
C24 C23 C22 120.90(12)
C24 C23 H23 119.6
C22 C23 H23 119.6
C23 C24 C25 119.93(14)
C23 C24 H24 120.0
C25 C24 H24 120.0
C26 C25 C24 119.71(12)
C26 C25 H25 120.1
C24 C25 H25 120.1
C25 C26 C27 120.33(13)
C25 C26 H26 119.8
C27 C26 H26 119.8
C22 C27 C26 120.48(14)
C22 C27 H27 119.8
C26 C27 H27 119.8
C1 O1 H1 109.5
C20 O4 C21 117.16(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.4246(15)
C1 C7 1.5301(16)
C1 C6 1.5332(16)
C1 C2 1.5537(16)
C2 C13 1.5225(15)
C2 C3 1.5339(16)
C2 H2 1.0000
C3 C4 1.5346(16)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C20 1.5089(16)
C4 C5 1.5465(16)
C4 H4 1.0000
C5 C22 1.5149(16)
C5 C6 1.5369(16)
C5 H5 1.0000
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.3896(17)
C7 C12 1.3995(18)
C8 C9 1.396(2)
C8 H8 0.9500
C9 C10 1.386(2)
C9 H9 0.9500
C10 C11 1.389(2)
C10 H10 0.9500
C11 C12 1.3869(18)
C11 H11 0.9500
C12 H12 0.9500
C13 O2 1.2259(16)
C13 C14 1.4909(16)
C14 C19 1.3947(18)
C14 C15 1.4028(16)
C15 C16 1.3855(18)
C15 H15 0.9500
C16 C17 1.391(2)
C16 H16 0.9500
C17 C18 1.3856(18)
C17 H17 0.9500
C18 C19 1.3902(17)
C18 H18 0.9500
C19 H19 0.9500
C20 O3 1.2137(16)
C20 O4 1.3351(15)
C21 O4 1.4478(16)
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
C22 C27 1.3935(17)
C22 C23 1.3960(19)
C23 C24 1.3905(17)
C23 H23 0.9500
C24 C25 1.392(2)
C24 H24 0.9500
C25 C26 1.383(2)
C25 H25 0.9500
C26 C27 1.3970(18)
C26 H26 0.9500
C27 H27 0.9500
O1 H1 0.8400
