#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/48/2224825.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_2224825
loop_
_publ_author_name
'Wang, Yifeng'
'Zhang, Wei'
'Xu, Xiangsheng'
'Zhang, Guangcun'
_publ_section_title
;(4R)-Ethyl
 4-(4-chlorophenyl)-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano[3,2-c]chromene-2-carboxylate
;
_journal_coeditor_code           ZQ2019
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o217
_journal_paper_doi               10.1107/S1600536809051976
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H17 Cl O6'
_chemical_formula_moiety         'C21 H17 Cl O6'
_chemical_formula_sum            'C21 H17 Cl O6'
_chemical_formula_weight         400.80
_chemical_name_systematic
;
(4R)-Ethyl 4-(4-chlorophenyl)-2-hydroxy
-5-oxo-2,3,4,5-tetrahydropyrano[3,2-c]chromene-2-carboxylate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 94.6807(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.4818(3)
_cell_length_b                   14.8358(7)
_cell_length_c                   11.3403(6)
_cell_measurement_reflns_used    7553
_cell_measurement_temperature    296.0(10)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.3
_cell_volume                     919.20(8)
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku, 2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku, 2006)'
_computing_data_reduction        'CrystalStructure (Rigaku, 2007)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.0(10)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rolling anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8978
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.198
_refine_ls_abs_structure_details 'Flack (1983), 1434 Friedel pairs'
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3606
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.040
_refine_ls_R_factor_gt           0.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0403P)²+0.1100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.073
_refine_ls_wR_factor_ref         0.080
_reflns_number_gt                3027
_reflns_number_total             3606
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            zq2019.cif
_cod_data_source_block           I
_cod_database_code               2224825
_cod_database_fobs_code          2224825
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C19 0.7695(3) 0.87640(13) 0.68614(17) 0.0368(4) Uani d . 1 . .
O O6 0.9549(3) 0.87424(10) 0.76723(12) 0.0456(3) Uani d . 1 . .
O O5 0.6200(3) 0.93532(10) 0.67137(15) 0.0542(4) Uani d . 1 . .
C C20 0.9886(5) 0.95257(18) 0.8444(2) 0.0577(6) Uani d . 1 . .
H H20A 0.8533 0.9579 0.8940 0.069 Uiso calc R 1 . .
H H20B 0.9965 1.0072 0.7978 0.069 Uiso calc R 1 . .
C C21 1.2228(5) 0.9388(2) 0.9187(2) 0.0677(7) Uani d . 1 . .
H H21A 1.3564 0.9380 0.8690 0.081 Uiso calc R 1 . .
H H21B 1.2169 0.8825 0.9600 0.081 Uiso calc R 1 . .
H H21C 1.2458 0.9871 0.9749 0.081 Uiso calc R 1 . .
Cl Cl1 0.78443(13) 0.72613(6) -0.01510(5) 0.0714(2) Uani d . 1 . .
O O3 0.6428(2) 0.72598(9) 0.68482(11) 0.0369(3) Uani d . 1 . .
C C9 0.5060(3) 0.57839(13) 0.71703(16) 0.0345(4) Uani d . 1 . .
O O4 0.6019(2) 0.80479(9) 0.50872(12) 0.0396(3) Uani d . 1 . .
H H4 0.5259 0.8519 0.5155 0.047 Uiso calc R 1 . .
C C10 0.6604(3) 0.63786(12) 0.65397(16) 0.0325(4) Uani d . 1 . .
O O2 0.6645(3) 0.45423(9) 0.60916(14) 0.0467(4) Uani d . 1 . .
O O1 0.9452(3) 0.47428(10) 0.48350(16) 0.0577(5) Uani d . 1 . .
C C14 1.0913(3) 0.72144(15) 0.31531(17) 0.0407(4) Uani d . 1 . .
H H14 1.2357 0.7420 0.3552 0.049 Uiso calc R 1 . .
C C13 0.9207(3) 0.67714(13) 0.37856(16) 0.0334(4) Uani d . 1 . .
C C2 0.8067(3) 0.60639(12) 0.57288(16) 0.0335(4) Uani d . 1 . .
C C1 0.9793(3) 0.66573(12) 0.51166(16) 0.0332(4) Uani d . 1 . .
H H1 1.1406 0.6370 0.5222 0.040 Uiso calc R 1 . .
C C8 0.3482(4) 0.60857(15) 0.79984(18) 0.0429(5) Uani d . 1 . .
H H8 0.3403 0.6695 0.8184 0.051 Uiso calc R 1 . .
C C15 1.0524(4) 0.73588(16) 0.19483(18) 0.0459(5) Uani d . 1 . .
H H15 1.1688 0.7657 0.1540 0.055 Uiso calc R 1 . .
C C5 0.3671(5) 0.42524(15) 0.7439(2) 0.0547(6) Uani d . 1 . .
H H5 0.3721 0.3644 0.7248 0.066 Uiso calc R 1 . .
C C11 0.7569(3) 0.79097(12) 0.60903(16) 0.0320(4) Uani d . 1 . .
C C6 0.2158(5) 0.45589(17) 0.8250(2) 0.0603(7) Uani d . 1 . .
H H6 0.1184 0.4149 0.8618 0.072 Uiso calc R 1 . .
C C16 0.8385(4) 0.70536(14) 0.13638(18) 0.0438(5) Uani d . 1 . .
C C17 0.6664(4) 0.65979(16) 0.19587(19) 0.0476(5) Uani d . 1 . .
H H17 0.5232 0.6388 0.1554 0.057 Uiso calc R 1 . .
C C3 0.8158(4) 0.51022(13) 0.54999(19) 0.0421(5) Uani d . 1 . .
C C12 1.0021(3) 0.75658(12) 0.57806(17) 0.0334(4) Uani d . 1 . .
H H12A 1.1086 0.7491 0.6500 0.040 Uiso calc R 1 . .
H H12B 1.0763 0.8007 0.5289 0.040 Uiso calc R 1 . .
C C4 0.5140(4) 0.48726(14) 0.69059(19) 0.0414(5) Uani d . 1 . .
C C18 0.7094(3) 0.64567(14) 0.31706(18) 0.0409(4) Uani d . 1 . .
H H18 0.5944 0.6146 0.3573 0.049 Uiso calc R 1 . .
C C7 0.2036(4) 0.54659(17) 0.8539(2) 0.0544(6) Uani d . 1 . .
H H7 0.0988 0.5658 0.9093 0.065 Uiso calc R 1 . .
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O5 C19 O6 . . 126.54(19) ?
O5 C19 C11 . . 121.49(18) ?
O6 C19 C11 . . 111.95(17) ?
C19 O6 C20 . . 116.98(18) ?
O6 C20 C21 . . 106.9(2) ?
O6 C20 H20A . . 110.3 ?
C21 C20 H20A . . 110.3 ?
O6 C20 H20B . . 110.3 ?
C21 C20 H20B . . 110.3 ?
H20A C20 H20B . . 108.6 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C10 O3 C11 . . 116.05(14) ?
C4 C9 C8 . . 119.26(17) ?
C4 C9 C10 . . 117.16(18) ?
C8 C9 C10 . . 123.56(18) ?
C11 O4 H4 . . 109.5 ?
C2 C10 O3 . . 124.48(16) ?
C2 C10 C9 . . 121.85(17) ?
O3 C10 C9 . . 113.68(16) ?
C4 O2 C3 . . 121.76(15) ?
C15 C14 C13 . . 121.85(17) ?
C15 C14 H14 . . 119.1 ?
C13 C14 H14 . . 119.1 ?
C18 C13 C14 . . 118.06(17) ?
C18 C13 C1 . . 124.12(17) ?
C14 C13 C1 . . 117.82(15) ?
C10 C2 C3 . . 119.47(17) ?
C10 C2 C1 . . 122.87(17) ?
C3 C2 C1 . . 117.45(17) ?
C2 C1 C13 . . 115.59(15) ?
C2 C1 C12 . . 108.35(15) ?
C13 C1 C12 . . 112.80(15) ?
C2 C1 H1 . . 106.5 ?
C13 C1 H1 . . 106.5 ?
C12 C1 H1 . . 106.5 ?
C7 C8 C9 . . 119.3(2) ?
C7 C8 H8 . . 120.3 ?
C9 C8 H8 . . 120.3 ?
C16 C15 C14 . . 118.80(19) ?
C16 C15 H15 . . 120.6 ?
C14 C15 H15 . . 120.6 ?
C6 C5 C4 . . 118.5(2) ?
C6 C5 H5 . . 120.8 ?
C4 C5 H5 . . 120.8 ?
O4 C11 O3 . . 108.53(14) ?
O4 C11 C12 . . 111.09(15) ?
O3 C11 C12 . . 110.24(14) ?
O4 C11 C19 . . 110.03(15) ?
O3 C11 C19 . . 102.12(14) ?
C12 C11 C19 . . 114.36(15) ?
C5 C6 C7 . . 121.7(2) ?
C5 C6 H6 . . 119.2 ?
C7 C6 H6 . . 119.2 ?
C15 C16 C17 . . 121.02(19) ?
C15 C16 Cl1 . . 119.04(17) ?
C17 C16 Cl1 . . 119.94(16) ?
C16 C17 C18 . . 119.28(18) ?
C16 C17 H17 . . 120.4 ?
C18 C17 H17 . . 120.4 ?
O1 C3 O2 . . 116.45(18) ?
O1 C3 C2 . . 125.38(19) ?
O2 C3 C2 . . 118.17(17) ?
C11 C12 C1 . . 111.80(14) ?
C11 C12 H12A . . 109.3 ?
C1 C12 H12A . . 109.3 ?
C11 C12 H12B . . 109.3 ?
C1 C12 H12B . . 109.3 ?
H12A C12 H12B . . 107.9 ?
O2 C4 C9 . . 121.55(17) ?
O2 C4 C5 . . 117.07(19) ?
C9 C4 C5 . . 121.4(2) ?
C13 C18 C17 . . 120.96(19) ?
C13 C18 H18 . . 119.5 ?
C17 C18 H18 . . 119.5 ?
C8 C7 C6 . . 119.9(2) ?
C8 C7 H7 . . 120.1 ?
C6 C7 H7 . . 120.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C19 O5 . 1.201(3) ?
C19 O6 . 1.314(2) ?
C19 C11 . 1.538(3) ?
O6 C20 . 1.457(3) ?
C20 C21 . 1.491(3) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
Cl1 C16 . 1.747(2) ?
O3 C10 . 1.359(2) ?
O3 C11 . 1.466(2) ?
C9 C4 . 1.386(3) ?
C9 C8 . 1.401(3) ?
C9 C10 . 1.451(3) ?
O4 C11 . 1.379(2) ?
O4 H4 . 0.8200 ?
C10 C2 . 1.352(3) ?
O2 C4 . 1.378(2) ?
O2 C3 . 1.385(3) ?
O1 C3 . 1.202(3) ?
C14 C15 . 1.382(3) ?
C14 C13 . 1.389(3) ?
C14 H14 . 0.9300 ?
C13 C18 . 1.384(3) ?
C13 C1 . 1.527(3) ?
C2 C3 . 1.452(3) ?
C2 C1 . 1.503(3) ?
C1 C12 . 1.544(2) ?
C1 H1 . 0.9800 ?
C8 C7 . 1.389(3) ?
C8 H8 . 0.9300 ?
C15 C16 . 1.376(3) ?
C15 H15 . 0.9300 ?
C5 C6 . 1.366(4) ?
C5 C4 . 1.393(3) ?
C5 H5 . 0.9300 ?
C11 C12 . 1.506(2) ?
C6 C7 . 1.388(4) ?
C6 H6 . 0.9300 ?
C16 C17 . 1.381(3) ?
C17 C18 . 1.391(3) ?
C17 H17 . 0.9300 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C18 H18 . 0.9300 ?
C7 H7 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O4 H4 O2 2_656 0.82 2.27 2.9184(19) 136
O4 H4 O5 . 0.82 2.19 2.671(2) 118
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O5 C19 O6 C20 . . . . -2.5(3) ?
C11 C19 O6 C20 . . . . 178.81(17) ?
C19 O6 C20 C21 . . . . -173.86(19) ?
C11 O3 C10 C2 . . . . 11.5(3) ?
C11 O3 C10 C9 . . . . -168.76(14) ?
C4 C9 C10 C2 . . . . -0.1(3) ?
C8 C9 C10 C2 . . . . -178.63(19) ?
C4 C9 C10 O3 . . . . -179.89(16) ?
C8 C9 C10 O3 . . . . 1.6(3) ?
C15 C14 C13 C18 . . . . 1.2(3) ?
C15 C14 C13 C1 . . . . -179.16(19) ?
O3 C10 C2 C3 . . . . 178.07(17) ?
C9 C10 C2 C3 . . . . -1.7(3) ?
O3 C10 C2 C1 . . . . 3.5(3) ?
C9 C10 C2 C1 . . . . -176.26(16) ?
C10 C2 C1 C13 . . . . -114.25(19) ?
C3 C2 C1 C13 . . . . 71.1(2) ?
C10 C2 C1 C12 . . . . 13.4(2) ?
C3 C2 C1 C12 . . . . -161.21(16) ?
C18 C13 C1 C2 . . . . 7.8(3) ?
C14 C13 C1 C2 . . . . -171.77(17) ?
C18 C13 C1 C12 . . . . -117.64(19) ?
C14 C13 C1 C12 . . . . 62.8(2) ?
C4 C9 C8 C7 . . . . 0.1(3) ?
C10 C9 C8 C7 . . . . 178.6(2) ?
C13 C14 C15 C16 . . . . 0.0(3) ?
C10 O3 C11 O4 . . . . 79.38(18) ?
C10 O3 C11 C12 . . . . -42.5(2) ?
C10 O3 C11 C19 . . . . -164.42(14) ?
O5 C19 C11 O4 . . . . 16.0(2) ?
O6 C19 C11 O4 . . . . -165.19(15) ?
O5 C19 C11 O3 . . . . -99.1(2) ?
O6 C19 C11 O3 . . . . 79.70(17) ?
O5 C19 C11 C12 . . . . 141.84(19) ?
O6 C19 C11 C12 . . . . -39.4(2) ?
C4 C5 C6 C7 . . . . 0.7(4) ?
C14 C15 C16 C17 . . . . -1.0(3) ?
C14 C15 C16 Cl1 . . . . 178.24(17) ?
C15 C16 C17 C18 . . . . 0.8(3) ?
Cl1 C16 C17 C18 . . . . -178.46(16) ?
C4 O2 C3 O1 . . . . 177.8(2) ?
C4 O2 C3 C2 . . . . -2.0(3) ?
C10 C2 C3 O1 . . . . -177.1(2) ?
C1 C2 C3 O1 . . . . -2.2(3) ?
C10 C2 C3 O2 . . . . 2.7(3) ?
C1 C2 C3 O2 . . . . 177.59(16) ?
O4 C11 C12 C1 . . . . -60.5(2) ?
O3 C11 C12 C1 . . . . 59.81(19) ?
C19 C11 C12 C1 . . . . 174.18(15) ?
C2 C1 C12 C11 . . . . -44.01(19) ?
C13 C1 C12 C11 . . . . 85.26(18) ?
C3 O2 C4 C9 . . . . 0.2(3) ?
C3 O2 C4 C5 . . . . 179.2(2) ?
C8 C9 C4 O2 . . . . 179.47(18) ?
C10 C9 C4 O2 . . . . 0.9(3) ?
C8 C9 C4 C5 . . . . 0.5(3) ?
C10 C9 C4 C5 . . . . -178.09(19) ?
C6 C5 C4 O2 . . . . -180.0(2) ?
C6 C5 C4 C9 . . . . -0.9(3) ?
C14 C13 C18 C17 . . . . -1.5(3) ?
C1 C13 C18 C17 . . . . 178.97(18) ?
C16 C17 C18 C13 . . . . 0.5(3) ?
C9 C8 C7 C6 . . . . -0.3(3) ?
C5 C6 C7 C8 . . . . -0.1(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744058
