#------------------------------------------------------------------------------
#$Date: 2016-03-22 22:06:50 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179032 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/30/4123092.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_4123092
loop_
_publ_author_name
'Yao, Weijun'
'Dou, Xiaowei'
'Lu, Yixin'
_publ_section_title
;
 Highly Enantioselective Synthesis of 3,4-Dihydropyrans through a
 Phosphine-Catalyzed [4+2] Annulation of Allenones and β,γ-Unsaturated
 α-Keto Esters.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              54
_journal_page_last               57
_journal_paper_doi               10.1021/ja5109358
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C18 H20 O4'
_chemical_formula_weight         300.34
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5979(6)
_cell_length_b                   11.4138(13)
_cell_length_c                   23.919(3)
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.31
_cell_measurement_theta_min      3.70
_cell_volume                     1528.3(3)
_computing.cell_refinement       'APEX2 v2013.6--2 (Bruker AXS)'
_computing.data_collection       'APEX2 (Bruker AXS)'
_computing.data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing.molecular_graphics    'Bruker SHELXTL'
_computing.publication_material  'Bruker SHELXTL'
_computing.structure_refinement  'SHELXL--2013 (Sheldrick 2013)'
_computing.structure_solution    'SHELXS--97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            25256
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.322
_diffrn_reflns_theta_min         3.696
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
; 
 Flack x determined using 1136 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.024
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0384P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0876
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2780
_reflns_number_total             2810
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5109358_si_002.cif
_cod_data_source_block           D707
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/COD-crude-data--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 2935 2014-11-11 08:27:57Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 4123091--4123092.cif.
;
_cod_original_cell_volume        1528.2(3)
_cod_database_code               4123092
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.4309(2) 0.39258(10) 0.68741(5) 0.0221(3) Uani 1 1 d . .
O2 O 1.0076(2) 0.42060(10) 0.57213(5) 0.0280(3) Uani 1 1 d . .
O3 O 0.1098(2) 0.33175(10) 0.76200(5) 0.0248(3) Uani 1 1 d . .
O4 O -0.0730(2) 0.50697(11) 0.75680(5) 0.0218(3) Uani 1 1 d . .
C1 C 0.2729(3) 0.47956(14) 0.70306(6) 0.0183(3) Uani 1 1 d . .
C2 C 0.2912(3) 0.59115(14) 0.68811(6) 0.0192(3) Uani 1 1 d . .
H2 H 0.1745 0.6461 0.7001 0.023 Uiso 1 1 calc R U
C3 C 0.4959(3) 0.63078(13) 0.65221(7) 0.0182(3) Uani 1 1 d . .
H3 H 0.6291 0.6564 0.6772 0.022 Uiso 1 1 calc R U
C4 C 0.5846(3) 0.52668(13) 0.61670(6) 0.0201(4) Uani 1 1 d . .
H4A H 0.4724 0.5145 0.5852 0.024 Uiso 1 1 calc R U
H4B H 0.7424 0.5468 0.6006 0.024 Uiso 1 1 calc R U
C5 C 0.6071(3) 0.41454(14) 0.64867(6) 0.0180(3) Uani 1 1 d . .
C6 C 0.7636(3) 0.32585(14) 0.64092(6) 0.0193(4) Uani 1 1 d . .
C7 C 0.7341(3) 0.21263(15) 0.67298(7) 0.0238(4) Uani 1 1 d . .
H7A H 0.6071 0.2218 0.7009 0.036 Uiso 1 1 calc R U
H7B H 0.8843 0.1932 0.6918 0.036 Uiso 1 1 calc R U
H7C H 0.6916 0.1495 0.6470 0.036 Uiso 1 1 calc R U
C8 C 0.9619(3) 0.33368(14) 0.59969(7) 0.0196(3) Uani 1 1 d . .
C9 C 1.1168(3) 0.22538(15) 0.59292(8) 0.0265(4) Uani 1 1 d . .
H9A H 1.1957 0.2081 0.6290 0.032 Uiso 1 1 calc R U
H9B H 1.0133 0.1578 0.5835 0.032 Uiso 1 1 calc R U
C10 C 1.3065(3) 0.23831(16) 0.54802(7) 0.0265(4) Uani 1 1 d . .
H10A H 1.2297 0.2430 0.5113 0.040 Uiso 1 1 calc R U
H10B H 1.4135 0.1704 0.5490 0.040 Uiso 1 1 calc R U
H10C H 1.3988 0.3099 0.5548 0.040 Uiso 1 1 calc R U
C11 C 0.0966(3) 0.42942(14) 0.74328(6) 0.0183(3) Uani 1 1 d . .
C12 C -0.2413(3) 0.46609(15) 0.79830(7) 0.0243(4) Uani 1 1 d . .
H12A H -0.3206 0.3951 0.7847 0.036 Uiso 1 1 calc R U
H12B H -0.3610 0.5270 0.8053 0.036 Uiso 1 1 calc R U
H12C H -0.1562 0.4485 0.8331 0.036 Uiso 1 1 calc R U
C13 C 0.4337(3) 0.73169(13) 0.61328(6) 0.0175(3) Uani 1 1 d . .
C14 C 0.5926(3) 0.82487(14) 0.60639(6) 0.0195(3) Uani 1 1 d . .
H14 H 0.7350 0.8279 0.6279 0.023 Uiso 1 1 calc R U
C15 C 0.5430(3) 0.91344(14) 0.56804(7) 0.0228(4) Uani 1 1 d . .
H15 H 0.6525 0.9762 0.5633 0.027 Uiso 1 1 calc R U
C16 C 0.3342(3) 0.91048(14) 0.53662(7) 0.0228(4) Uani 1 1 d . .
H16 H 0.3003 0.9714 0.5107 0.027 Uiso 1 1 calc R U
C17 C 0.1757(3) 0.81819(14) 0.54325(7) 0.0227(4) Uani 1 1 d . .
H17 H 0.0331 0.8155 0.5218 0.027 Uiso 1 1 calc R U
C18 C 0.2256(3) 0.72945(14) 0.58139(7) 0.0200(4) Uani 1 1 d . .
H18 H 0.1162 0.6665 0.5857 0.024 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C5 O1 C1 120.69(12)
C11 O4 C12 114.50(13)
C2 C1 O1 124.58(15)
C2 C1 C11 126.35(15)
O1 C1 C11 108.82(13)
C1 C2 C3 120.14(15)
C1 C2 H2 119.9
C3 C2 H2 119.9
C2 C3 C13 113.80(13)
C2 C3 C4 109.18(13)
C13 C3 C4 108.64(12)
C2 C3 H3 108.4
C13 C3 H3 108.4
C4 C3 H3 108.4
C5 C4 C3 113.86(13)
C5 C4 H4A 108.8
C3 C4 H4A 108.8
C5 C4 H4B 108.8
C3 C4 H4B 108.8
H4A C4 H4B 107.7
C6 C5 O1 114.86(14)
C6 C5 C4 128.69(15)
O1 C5 C4 116.08(14)
C5 C6 C8 121.98(15)
C5 C6 C7 119.99(15)
C8 C6 C7 117.98(14)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
O2 C8 C6 124.37(15)
O2 C8 C9 119.03(14)
C6 C8 C9 116.60(14)
C10 C9 C8 113.31(14)
C10 C9 H9A 108.9
C8 C9 H9A 108.9
C10 C9 H9B 108.9
C8 C9 H9B 108.9
H9A C9 H9B 107.7
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O3 C11 O4 124.52(15)
O3 C11 C1 123.65(16)
O4 C11 C1 111.81(13)
O4 C12 H12A 109.5
O4 C12 H12B 109.5
H12A C12 H12B 109.5
O4 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C18 C13 C14 118.82(14)
C18 C13 C3 120.83(15)
C14 C13 C3 120.22(15)
C15 C14 C13 120.24(15)
C15 C14 H14 119.9
C13 C14 H14 119.9
C16 C15 C14 120.40(16)
C16 C15 H15 119.8
C14 C15 H15 119.8
C17 C16 C15 119.65(15)
C17 C16 H16 120.2
C15 C16 H16 120.2
C16 C17 C18 119.98(16)
C16 C17 H17 120.0
C18 C17 H17 120.0
C17 C18 C13 120.90(15)
C17 C18 H18 119.6
C13 C18 H18 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.376(2)
O1 C1 1.381(2)
O2 C8 1.218(2)
O3 C11 1.204(2)
O4 C11 1.338(2)
O4 C12 1.446(2)
C1 C2 1.327(2)
C1 C11 1.493(2)
C2 C3 1.502(2)
C2 H2 0.9500
C3 C13 1.521(2)
C3 C4 1.543(2)
C3 H3 1.0000
C4 C5 1.496(2)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.351(2)
C6 C8 1.488(2)
C6 C7 1.512(2)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 C9 1.519(2)
C9 C10 1.518(2)
C9 H9A 0.9900
C9 H9B 0.9900
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 C18 1.393(2)
C13 C14 1.396(2)
C14 C15 1.393(2)
C14 H14 0.9500
C15 C16 1.390(2)
C15 H15 0.9500
C16 C17 1.386(2)
C16 H16 0.9500
C17 C18 1.391(2)
C17 H17 0.9500
C18 H18 0.9500
