#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/99/2009991.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2009991
loop_
_publ_author_name
'Valla, Alain'
'Giraud, Michel'
'Ginderow, Daria'
_publ_section_title
;Synthèses et structures de deux acides
 5,6-dihydro-6-[aryl]-4-{2-[aryl]-éthényl}-2-oxo-2H-pyrane-3-carboxylique
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1314
_journal_page_last               1318
_journal_paper_doi               10.1107/S0108270194001423
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C22 H20 O6'
_chemical_formula_sum            'C22 H20 O6'
_chemical_formula_weight         380.40
_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_type_scat_source           IntTabIV
_cell_angle_alpha                90.0
_cell_angle_beta                 99.57(4)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   20.533(8)
_cell_length_b                   7.683(3)
_cell_length_c                   12.088(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      22
_cell_measurement_theta_min      11
_cell_volume                     1880.4(13)
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Philips PW1100'
_diffrn_measurement_method       "'flying stepscan' (Logiciel Philips)"
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'tube \`a rayons X'
_diffrn_radiation_type           'radiation: Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3483
_diffrn_reflns_theta_max         68.15
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        <2.9
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.78
_exptl_absorpt_correction_type   'pas de correction d'absorption'
_exptl_crystal_colour            jaune-orange
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       prismatique
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.139
_refine_ls_extinction_method     'pas de correction d'extinction'
_refine_ls_goodness_of_fit_obs   1.849
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           compl\`ete
_refine_ls_number_constraints    0
_refine_ls_number_parameters     253
_refine_ls_number_reflns         1303
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.041
_refine_ls_shift/esd_max         0.093
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=1
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.040
_reflns_number_observed          1303
_reflns_number_total             3087
_reflns_observed_criterion
;F>5.48 (\'echelle absolue)
0.090<Sin\q/\l<0.540 \%A^-1^
;
_cod_data_source_file            pa1097.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w=1' was changed to 'calc'. New
tag '_refine_ls_weighting_details' was created. The value of the new
tag was set to 'w=1'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1880.41
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2009991
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, 1/2-y, 1/2+z'
'-x, -y, -z'
'-x, 1/2+y, 1/2-z'
loop_
_atom_site_aniso_label
_atom_site_aniso_type_symbol
O(1) O
O(2) O
O(3) O
O(4) O
O(5) O
O(6) O
C(2) C
C(3) C
C(4) C
C(5) C
C(6) C
C(7) C
C(8) C
C(9) C
C(10) C
C(11) C
C(12) C
C(13) C
C(14) C
C(15) C
C(16) C
C(17) C
C(18) C
C(19) C
C(20) C
C(21) C
C(22) C
C(23) C
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_type_symbol
O(1) 0.14900(10) -0.0157(4) 0.0873(3) Beq ? ? O
O(2) 0.1445(2) 0.1160(5) 0.2452(3) Beq ? ? O
O(3) 0.3200(2) -0.0812(5) 0.4042(3) Beq ? ? O
O(4) 0.2303(2) 0.0702(5) 0.4172(3) Beq ? ? O
O(5) 0.0241(2) -0.1386(5) -0.4013(2) Beq ? ? O
O(6) 0.6743(2) -0.1519(5) 0.2127(3) Beq ? ? O
C(2) 0.1772(2) 0.0252(7) 0.1915(4) Beq ? ? C
C(3) 0.2452(2) -0.0304(6) 0.2341(4) Beq ? ? C
C(4) 0.2857(2) -0.0702(6) 0.1585(4) Beq ? ? C
C(5) 0.2540(2) -0.0890(6) 0.0369(3) Beq ? ? C
C(6) 0.1836(2) -0.1430(6) 0.0261(4) Beq ? ? C
C(7) 0.1440(2) -0.1508(6) -0.0905(4) Beq ? ? C
C(8) 0.0942(2) -0.2702(7) -0.1146(4) Beq ? ? C
C(9) 0.0529(2) -0.2712(7) -0.2173(4) Beq ? ? C
C(10) 0.0627(2) -0.1521(7) -0.2978(4) Beq ? ? C
C(11) 0.1131(2) -0.0346(7) -0.2770(4) Beq ? ? C
C(12) 0.1541(2) -0.0322(7) -0.1721(4) Beq ? ? C
C(13) 0.2693(3) -0.0153(7) 0.3582(4) Beq ? ? C
C(14) 0.3565(2) -0.0855(6) 0.1867(4) Beq ? ? C
C(15) 0.3975(2) -0.1283(6) 0.1158(4) Beq ? ? C
C(16) 0.4686(2) -0.1332(6) 0.1441(4) Beq ? ? C
C(17) 0.5069(2) -0.1963(7) 0.0676(4) Beq ? ? C
C(18) 0.5749(2) -0.2038(7) 0.0924(4) Beq ? ? C
C(19) 0.6069(2) -0.1425(6) 0.1947(4) Beq ? ? C
C(20) 0.5707(2) -0.0781(7) 0.2721(4) Beq ? ? C
C(21) 0.5027(3) -0.0727(7) 0.2466(4) Beq ? ? C
C(22) 0.7085(2) -0.0966(7) 0.3200(5) Beq ? ? C
C(23) -0.0277(3) -0.2627(8) -0.4300(4) Beq ? ? C
H(4) 0.194(2) 0.123(5) 0.359(3) Biso ? ? H
H(5a) 0.279(2) -0.177(6) -0.001(3) Biso ? ? H
H(5b) 0.260(2) 0.038(6) 0.000(3) Biso ? ? H
H(6) 0.180(2) -0.267(5) 0.066(3) Biso ? ? H
H(8) 0.090(2) -0.368(5) -0.056(3) Biso ? ? H
H(9) 0.021(2) -0.369(5) -0.235(3) Biso ? ? H
H(11) 0.116(2) 0.066(5) -0.331(3) Biso ? ? H
H(12) 0.190(2) 0.057(5) -0.163(3) Biso ? ? H
H(14) 0.376(2) -0.055(5) 0.262(3) Biso ? ? H
H(15) 0.379(2) -0.164(6) 0.036(3) Biso ? ? H
H(17) 0.482(2) -0.242(5) -0.007(3) Biso ? ? H
H(18) 0.605(2) -0.242(5) 0.038(3) Biso ? ? H
H(20) 0.590(2) -0.035(5) 0.344(3) Biso ? ? H
H(21) 0.478(2) -0.019(5) 0.301(3) Biso ? ? H
H(22a) 0.701(2) 0.029(6) 0.329(3) Biso ? ? H
H(22b) 0.693(2) -0.178(6) 0.380(3) Biso ? ? H
H(22c) 0.758(2) -0.128(6) 0.326(3) Biso ? ? H
H(23a) -0.061(2) -0.248(5) -0.378(3) Biso ? ? H
H(23b) -0.047(2) -0.241(5) -0.502(3) Biso ? ? H
H(23c) -0.012(2) -0.392(6) -0.428(3) Biso ? ? H
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 2 -2
2 2 0
0 -2 2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(2) O(1) C(6) 117.4(3) yes
C(10) O(5) C(23) 117.7(4) yes
C(19) O(6) C(22) 117.4(4) yes
O(2) C(2) O(1) 116.4(4) yes
O(2) C(2) C(3) 123.5(4) yes
O(1) C(2) C(3) 120.0(4) yes
C(4) C(3) C(2) 118.6(4) yes
C(4) C(3) C(13) 123.2(4) yes
C(2) C(3) C(13) 117.5(4) yes
C(3) C(4) C(14) 124.1(4) yes
C(3) C(4) C(5) 117.3(4) yes
C(14) C(4) C(5) 118.5(4) yes
C(6) C(5) C(4) 111.5(4) yes
O(1) C(6) C(5) 108.2(3) yes
O(1) C(6) C(7) 105.3(3) yes
C(5) C(6) C(7) 117.3(4) yes
C(8) C(7) C(12) 119.0(4) yes
C(8) C(7) C(6) 119.6(4) yes
C(12) C(7) C(6) 121.3(4) yes
C(7) C(8) C(9) 121.3(5) yes
C(10) C(9) C(8) 119.5(4) yes
C(11) C(10) O(5) 115.1(4) yes
C(11) C(10) C(9) 120.4(4) yes
O(5) C(10) C(9) 124.5(4) yes
C(10) C(11) C(12) 119.9(5) yes
C(7) C(12) C(11) 119.9(4) yes
O(3) C(13) O(4) 120.7(4) yes
O(3) C(13) C(3) 122.8(5) yes
O(4) C(13) C(3) 116.4(4) yes
C(15) C(14) C(4) 125.8(4) yes
C(14) C(15) C(16) 125.0(4) yes
C(17) C(16) C(21) 116.7(4) yes
C(17) C(16) C(15) 120.7(4) yes
C(21) C(16) C(15) 122.6(4) yes
C(18) C(17) C(16) 122.1(4) yes
C(17) C(18) C(19) 119.5(5) yes
O(6) C(19) C(20) 123.8(4) yes
O(6) C(19) C(18) 116.3(4) yes
C(20) C(19) C(18) 120.0(4) yes
C(21) C(20) C(19) 119.9(4) yes
C(20) C(21) C(16) 121.8(5) yes
H(4) O(4) C(13) 105(2) ?
H(5a) C(5) H(5b) 108(3) ?
H(5a) C(5) C(6) 109(2) ?
H(5a) C(5) C(4) 110(2) ?
H(5b) C(5) C(6) 113(2) ?
H(5b) C(5) C(4) 105(2) ?
H(6) C(6) O(1) 107(2) ?
H(6) C(6) C(5) 110(2) ?
H(6) C(6) C(7) 108(2) ?
H(8) C(8) C(7) 118(2) ?
H(8) C(8) C(9) 120(2) ?
H(9) C(9) C(10) 121(2) ?
H(9) C(9) C(8) 119(2) ?
H(11) C(11) C(10) 121(2) ?
H(11) C(11) C(12) 118(2) ?
H(12) C(12) C(7) 125(2) ?
H(12) C(12) C(11) 116(2) ?
H(14) C(14) C(15) 118(2) ?
H(14) C(14) C(4) 116(2) ?
H(15) C(15) C(14) 119(2) ?
H(15) C(15) C(16) 116(2) ?
H(17) C(17) C(18) 121(2) ?
H(17) C(17) C(16) 117(2) ?
H(18) C(18) C(17) 125(2) ?
H(18) C(18) C(19) 115(2) ?
H(20) C(20) C(21) 116(2) ?
H(20) C(20) C(19) 124(2) ?
H(21) C(21) C(20) 119(2) ?
H(21) C(21) C(16) 119(2) ?
H(22a) C(22) H(22b) 116(3) ?
H(22a) C(22) H(22c) 113(3) ?
H(22a) C(22) O(6) 109(2) ?
H(22b) C(22) H(22c) 103(3) ?
H(22b) C(22) O(6) 107(2) ?
H(22c) C(22) O(6) 109(2) ?
H(23b) C(23) H(23a) 111(3) ?
H(23b) C(23) H(23c) 106(3) ?
H(23b) C(23) O(5) 107(3) ?
H(23a) C(23) H(23c) 109(3) ?
H(23a) C(23) O(5) 109(2) ?
H(23c) C(23) O(5) 114(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(2) . . 1.333(5) yes
O(1) C(6) . . 1.478(6) yes
O(2) C(2) . . 1.226(6) yes
O(3) C(13) . . 1.206(6) yes
O(4) C(13) . . 1.331(7) yes
O(5) C(10) . . 1.368(5) yes
O(5) C(23) . . 1.428(6) yes
O(6) C(19) . . 1.366(5) yes
O(6) C(22) . . 1.434(6) yes
C(2) C(3) . . 1.471(6) yes
C(3) C(4) . . 1.368(6) yes
C(3) C(13) . . 1.504(6) yes
C(4) C(14) . . 1.442(6) yes
C(4) C(5) . . 1.513(6) yes
C(5) C(6) . . 1.488(6) yes
C(6) C(7) . . 1.507(6) yes
C(7) C(8) . . 1.369(7) yes
C(7) C(12) . . 1.383(7) yes
C(8) C(9) . . 1.382(6) yes
C(9) C(10) . . 1.375(7) yes
C(10) C(11) . . 1.364(7) yes
C(11) C(12) . . 1.401(6) yes
C(14) C(15) . . 1.338(7) yes
C(15) C(16) . . 1.444(6) yes
C(16) C(17) . . 1.397(7) yes
C(16) C(21) . . 1.397(6) yes
C(17) C(18) . . 1.379(7) yes
C(18) C(19) . . 1.382(6) yes
C(19) C(20) . . 1.380(7) yes
C(20) C(21) . . 1.379(7) yes
O(4) H(4) . . 1.02(4) ?
C(5) H(5a) . . 1.00(4) ?
C(5) H(5b) . . 1.09(4) ?
C(6) H(6) . . 1.07(4) ?
C(8) H(8) . . 1.05(4) ?
C(9) H(9) . . 1.00(4) ?
C(11) H(11) . . 1.02(4) ?
C(12) H(12) . . 0.99(4) ?
C(14) H(14) . . 0.95(4) ?
C(15) H(15) . . 1.01(4) ?
C(17) H(17) . . 1.02(4) ?
C(18) H(18) . . 1.01(4) ?
C(20) H(20) . . 0.95(4) ?
C(21) H(21) . . 0.98(4) ?
C(22) H(22a) . . 0.98(4) ?
C(22) H(22b) . . 1.04(4) ?
C(22) H(22c) . . 1.05(4) ?
C(23) H(23b) . . 0.91(4) ?
C(23) H(23a) . . 1.01(4) ?
C(23) H(23c) . . 1.04(4) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C(6) O(1) C(2) O(2) -172.3(4)
C(2) O(1) C(6) C(7) -175.1(4)
C(23) O(5) C(10) C(9) -3.5(7)
C(23) O(5) C(10) C(11) 177.3(4)
C(22) O(6) C(19) C(18) -177.2(4)
C(22) O(6) C(19) C(20) 2.2(7)
O(1) C(2) C(3) C(13) -167.1(4)
O(2) C(2) C(3) C(4) -154.9(5)
O(2) C(2) C(3) C(13) 16.4(7)
C(2) C(3) C(4) C(14) 164.5(4)
C(13) C(3) C(4) C(5) 177.3(4)
C(13) C(3) C(4) C(14) -6.2(7)
C(2) C(3) C(13) O(3) 168.2(5)
C(2) C(3) C(13) O(4) -9.3(7)
C(4) C(3) C(13) O(3) -20.9(8)
C(4) C(3) C(13) O(4) 161.6(5)
C(14) C(4) C(5) C(6) 156.4(4)
C(3) C(4) C(14) C(15) 178.3(5)
C(5) C(4) C(14) C(15) -5.3(7)
C(4) C(5) C(6) C(7) 174.5(4)
O(1) C(6) C(7) C(8) -91.0(5)
O(1) C(6) C(7) C(12) 84.8(5)
C(5) C(6) C(7) C(8) 148.6(5)
C(5) C(6) C(7) C(12) -35.6(6)
C(6) C(7) C(8) C(9) 174.1(4)
C(6) C(7) C(12) C(11) -175.1(5)
C(8) C(9) C(10) O(5) -178.5(5)
O(5) C(10) C(11) C(12) 177.5(4)
C(4) C(14) C(15) C(16) 176.2(5)
C(14) C(15) C(16) C(17) 173.5(5)
C(14) C(15) C(16) C(21) -8.0(8)
C(15) C(16) C(17) C(18) -179.5(5)
C(15) C(16) C(21) C(20) -179.9(10)
C(17) C(18) C(19) O(6) -179.1(4)
O(6) C(19) C(20) C(21) 179.6(6)
