#------------------------------------------------------------------------------
#$Date: 2019-06-20 16:09:02 +0300 (Thu, 20 Jun 2019) $
#$Revision: 216388 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/17/1551776.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_1551776
loop_
_publ_author_name
'WANG, Tian-tian'
'LV, Zhi-liang'
'FENG, Ji-lu'
'SUN, Hai-ling'
'LIU, Jia'
'LI, Ke'
_publ_section_title
;
 Crystal Structure of
 (Z)-(+-)-2-(3,5-dimethoxyphenyl)-4-(4-methoxybenzylidene)tetrahydrofuran-3-carboxylic
 Acid
;
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              77
_journal_paper_doi               10.2116/xraystruct.25.77
_journal_volume                  25
_journal_year                    2009
_chemical_formula_sum            'C21 H22 O6'
_chemical_formula_weight         370.39
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.586(7)
_cell_angle_beta                 93.277(7)
_cell_angle_gamma                111.067(6)
_cell_formula_units_Z            2
_cell_length_a                   8.768(5)
_cell_length_b                   9.974(6)
_cell_length_c                   11.576(6)
_cell_measurement_reflns_used    814
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.022
_cell_measurement_theta_min      2.512
_cell_volume                     920.2(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3820
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_correction_T_min  0.9769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0600
_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)+(0.1301P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.1769
_reflns_number_gt                2481
_reflns_number_total             3172
_reflns_threshold_expression     ?>2sigma(I)
_cod_data_source_file            25_77_1.cif
_cod_data_source_block           f80905b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/andrius/struct/COD-crude-data/automatic-downloads/current/J-STAGE/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 6524 2018-11-02 12:15:13Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1551776
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.40982(18) 0.57555(14) 0.59805(11) 0.0485(4) Uani 1 1 d .
C1 C 0.3816(2) 0.6234(2) 0.71651(15) 0.0384(5) Uani 1 1 d .
H1 H 0.2888 0.6560 0.7140 0.046 Uiso 1 1 calc R
C2 C 0.5407(2) 0.75534(19) 0.76828(15) 0.0357(5) Uani 1 1 d .
H2 H 0.6227 0.7191 0.7969 0.043 Uiso 1 1 calc R
C3 C 0.5962(2) 0.8194(2) 0.66121(15) 0.0375(5) Uani 1 1 d .
C4 C 0.4884(3) 0.7058(2) 0.55543(16) 0.0466(5) Uani 1 1 d .
H4A H 0.4070 0.7385 0.5227 0.056 Uiso 1 1 calc R
H4B H 0.5543 0.6879 0.4943 0.056 Uiso 1 1 calc R
C5 C 0.3444(2) 0.5007(2) 0.78116(16) 0.0385(5) Uani 1 1 d .
C6 C 0.2114(2) 0.4684(2) 0.84369(18) 0.0448(5) Uani 1 1 d .
H6 H 0.1418 0.5201 0.8432 0.054 Uiso 1 1 calc R
C7 C 0.1816(2) 0.3584(2) 0.90748(18) 0.0466(5) Uani 1 1 d .
C8 C 0.2826(2) 0.2806(2) 0.90833(17) 0.0464(5) Uani 1 1 d .
H8 H 0.2608 0.2053 0.9494 0.056 Uiso 1 1 calc R
C9 C 0.4185(2) 0.3162(2) 0.84666(18) 0.0436(5) Uani 1 1 d .
C10 C 0.4495(2) 0.4242(2) 0.78303(16) 0.0420(5) Uani 1 1 d .
H10 H 0.5400 0.4463 0.7415 0.050 Uiso 1 1 calc R
C11 C 0.0137(3) 0.2260(3) 1.0347(2) 0.0727(8) Uani 1 1 d .
H11A H -0.0091 0.1320 0.9830 0.109 Uiso 1 1 calc R
H11B H -0.0805 0.2229 1.0741 0.109 Uiso 1 1 calc R
H11C H 0.1072 0.2485 1.0926 0.109 Uiso 1 1 calc R
C12 C 0.6714(3) 0.2850(3) 0.8206(3) 0.0685(7) Uani 1 1 d .
H12A H 0.6615 0.2748 0.7361 0.103 Uiso 1 1 calc R
H12B H 0.7313 0.2279 0.8430 0.103 Uiso 1 1 calc R
H12C H 0.7294 0.3868 0.8587 0.103 Uiso 1 1 calc R
C13 C 0.5208(2) 0.86430(19) 0.86902(15) 0.0346(4) Uani 1 1 d .
C14 C 0.7199(2) 0.9464(2) 0.66652(16) 0.0422(5) Uani 1 1 d .
H14 H 0.7741 0.9943 0.7426 0.051 Uiso 1 1 calc R
C15 C 0.7863(2) 1.0248(2) 0.57449(17) 0.0409(5) Uani 1 1 d .
C16 C 0.7125(3) 0.9855(2) 0.45618(18) 0.0487(5) Uani 1 1 d .
H16 H 0.6158 0.9026 0.4318 0.058 Uiso 1 1 calc R
C17 C 0.7803(3) 1.0674(2) 0.37581(19) 0.0528(6) Uani 1 1 d .
H17 H 0.7297 1.0389 0.2977 0.063 Uiso 1 1 calc R
C18 C 0.9234(2) 1.1919(2) 0.40977(17) 0.0462(5) Uani 1 1 d .
C19 C 0.9994(3) 1.2322(2) 0.52488(18) 0.0518(6) Uani 1 1 d .
H19 H 1.0966 1.3147 0.5487 0.062 Uiso 1 1 calc R
C20 C 0.9296(3) 1.1491(2) 0.60427(18) 0.0519(6) Uani 1 1 d .
H20 H 0.9814 1.1780 0.6821 0.062 Uiso 1 1 calc R
C21 C 1.1161(3) 1.4023(3) 0.3570(2) 0.0691(7) Uani 1 1 d .
H21A H 1.0908 1.4685 0.4169 0.104 Uiso 1 1 calc R
H21B H 1.1407 1.4450 0.2891 0.104 Uiso 1 1 calc R
H21C H 1.2098 1.3851 0.3877 0.104 Uiso 1 1 calc R
O2 O 0.38268(16) 0.86523(15) 0.88527(12) 0.0495(4) Uani 1 1 d .
O3 O 0.65436(16) 0.95387(15) 0.93397(11) 0.0465(4) Uani 1 1 d .
H3A H 0.6326 1.0065 0.9883 0.070 Uiso 1 1 calc R
O4 O 0.04815(19) 0.3350(2) 0.96793(16) 0.0699(5) Uani 1 1 d .
O5 O 0.51253(19) 0.23438(16) 0.85582(16) 0.0640(5) Uani 1 1 d .
O6 O 0.97938(19) 1.26764(19) 0.32354(14) 0.0653(5) 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 0.0016 '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'
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
C4 O1 C1 106.32(14)
O1 C1 C5 110.43(15)
O1 C1 C2 103.14(14)
C5 C1 C2 114.37(15)
O1 C1 H1 109.6
C5 C1 H1 109.6
C2 C1 H1 109.6
C13 C2 C3 113.66(15)
C13 C2 C1 114.00(15)
C3 C2 C1 103.38(15)
C13 C2 H2 108.5
C3 C2 H2 108.5
C1 C2 H2 108.5
C14 C3 C4 130.12(17)
C14 C3 C2 124.59(17)
C4 C3 C2 105.22(15)
O1 C4 C3 105.84(15)
O1 C4 H4A 110.6
C3 C4 H4A 110.6
O1 C4 H4B 110.6
C3 C4 H4B 110.6
H4A C4 H4B 108.7
C6 C5 C10 120.00(19)
C6 C5 C1 120.14(18)
C10 C5 C1 119.77(17)
C5 C6 C7 119.84(19)
C5 C6 H6 120.1
C7 C6 H6 120.1
O4 C7 C8 123.4(2)
O4 C7 C6 115.87(19)
C8 C7 C6 120.70(18)
C7 C8 C9 118.90(19)
C7 C8 H8 120.5
C9 C8 H8 120.5
O5 C9 C10 124.89(18)
O5 C9 C8 113.97(18)
C10 C9 C8 121.14(19)
C9 C10 C5 119.39(18)
C9 C10 H10 120.3
C5 C10 H10 120.3
O4 C11 H11A 109.5
O4 C11 H11B 109.5
H11A C11 H11B 109.5
O4 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O5 C12 H12A 109.5
O5 C12 H12B 109.5
H12A C12 H12B 109.5
O5 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
O2 C13 O3 123.56(17)
O2 C13 C2 120.89(16)
O3 C13 C2 115.56(17)
C3 C14 C15 131.68(18)
C3 C14 H14 114.2
C15 C14 H14 114.2
C20 C15 C16 116.26(18)
C20 C15 C14 119.02(17)
C16 C15 C14 124.70(19)
C17 C16 C15 121.1(2)
C17 C16 H16 119.4
C15 C16 H16 119.4
C16 C17 C18 120.67(19)
C16 C17 H17 119.7
C18 C17 H17 119.7
O6 C18 C19 124.35(19)
O6 C18 C17 116.17(18)
C19 C18 C17 119.49(19)
C20 C19 C18 119.1(2)
C20 C19 H19 120.5
C18 C19 H19 120.5
C19 C20 C15 123.39(19)
C19 C20 H20 118.3
C15 C20 H20 118.3
O6 C21 H21A 109.5
O6 C21 H21B 109.5
H21A C21 H21B 109.5
O6 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C13 O3 H3A 109.5
C7 O4 C11 118.05(19)
C9 O5 C12 117.53(17)
C18 O6 C21 117.92(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.427(2)
O1 C1 1.433(2)
C1 C5 1.497(3)
C1 C2 1.527(3)
C1 H1 0.9800
C2 C13 1.505(2)
C2 C3 1.523(3)
C2 H2 0.9800
C3 C14 1.327(3)
C3 C4 1.505(3)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.378(3)
C5 C10 1.393(3)
C6 C7 1.389(3)
C6 H6 0.9300
C7 O4 1.368(2)
C7 C8 1.373(3)
C8 C9 1.393(3)
C8 H8 0.9300
C9 O5 1.365(2)
C9 C10 1.371(3)
C10 H10 0.9300
C11 O4 1.403(3)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 O5 1.413(3)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 O2 1.239(2)
C13 O3 1.279(2)
C14 C15 1.461(3)
C14 H14 0.9300
C15 C20 1.382(3)
C15 C16 1.403(3)
C16 C17 1.371(3)
C16 H16 0.9300
C17 C18 1.384(3)
C17 H17 0.9300
C18 O6 1.369(2)
C18 C19 1.375(3)
C19 C20 1.373(3)
C19 H19 0.9300
C20 H20 0.9300
C21 O6 1.410(3)
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
O3 H3A 0.8200
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O2 0.82 1.80 2.617(2) 171.5 2_677
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
O1 C1 C2 C3 31.39(18)
C1 C2 C3 C4 -11.09(19)
C2 C3 C4 O1 -13.2(2)
C3 C4 O1 C1 34.5(2)
C2 C3 C14 C15 -178.44(19)
