#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/87/2218773.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_2218773
loop_
_publ_author_name
'Wojciechowski, Jakub'
'Krawczyk, Henryk'
'Albrecht, Łukasz'
'Wolf, Wojciech M.'
_publ_section_title
;rac-(1S,2R)-Diethyl
 6-hydroxy-1-(4-methoxyphenyl)-3-oxo-2,3-dihydro-1H-benzo[f]chromen-2-yl]phosphonate
;
_journal_coeditor_code           NG2458
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1240
_journal_page_last               o1241
_journal_paper_doi               10.1107/S1600536808015857
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C24 H25 O7 P'
_chemical_formula_moiety         'C24 H25 O7 P'
_chemical_formula_sum            'C24 H25 O7 P'
_chemical_formula_weight         456.41
_chemical_melting_point_gt       396
_chemical_melting_point_lt       398
_chemical_name_systematic
;
rac-(1S,2R)-Diethyl
6-hydroxy-1-(4-methoxyphenyl)-3-oxo-2,3-dihydro-1H-
benzo[f]chromen-2-yl]phosphonate
;
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.8060(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.6231(17)
_cell_length_b                   10.0018(8)
_cell_length_c                   22.4011(17)
_cell_measurement_reflns_used    8721
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.274
_cell_measurement_theta_min      2.236
_cell_volume                     4498.0(6)
_computing_cell_refinement       'SMART (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2008)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ω
_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  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            37601
_diffrn_reflns_theta_full        27.36
_diffrn_reflns_theta_max         27.36
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.364
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0450
_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)+(0.0691P)²+2.0425P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1366
_reflns_number_gt                3585
_reflns_number_total             5076
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2458.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2218773
_cod_database_fobs_code          2218773
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
P P 0.85826(2) 0.18689(5) 0.93687(3) 0.04719(16) Uani d . 1
O O1 0.86909(7) 0.50338(13) 0.99316(6) 0.0501(3) Uani d . 1
O O2 0.82123(8) 0.38041(16) 1.04447(7) 0.0612(4) Uani d . 1
O O3 0.82989(9) 0.07064(16) 0.96515(11) 0.0843(6) Uani d . 1
O O4 0.92748(7) 0.22132(16) 0.97264(8) 0.0645(4) Uani d . 1
O O5 0.84281(8) 0.14572(19) 0.86632(8) 0.0751(5) Uani d . 1
O O6 1.00680(7) 0.72224(17) 0.90165(8) 0.0694(5) Uani d . 1
O O7 0.54354(8) 0.70103(17) 0.84382(11) 0.0838(6) Uani d . 1
C C1 0.82904(10) 0.40053(19) 0.99520(10) 0.0464(4) Uani d . 1
C C2 0.79907(9) 0.31862(18) 0.93467(9) 0.0445(4) Uani d . 1
C C3 0.77848(9) 0.40694(18) 0.87347(9) 0.0433(4) Uani d . 1
C C4 0.83847(9) 0.49031(17) 0.87772(9) 0.0411(4) Uani d . 1
C C5 0.85316(9) 0.53228(18) 0.82352(9) 0.0432(4) Uani d . 1
C C6 0.91093(9) 0.60975(19) 0.83255(9) 0.0457(4) Uani d . 1
C C7 0.95280(9) 0.6475(2) 0.89610(10) 0.0492(5) Uani d . 1
C C8 0.93774(10) 0.60900(19) 0.94736(10) 0.0484(5) Uani d . 1
C C9 0.88100(9) 0.53133(18) 0.93693(9) 0.0435(4) Uani d . 1
C C10 0.81079(11) 0.5026(2) 0.75920(10) 0.0540(5) Uani d . 1
C C11 0.82642(13) 0.5444(2) 0.70810(11) 0.0616(6) Uani d . 1
C C12 0.88486(13) 0.6152(2) 0.71814(12) 0.0636(6) Uani d . 1
C C13 0.92573(12) 0.6490(2) 0.77862(11) 0.0567(5) Uani d . 1
C C14 0.71632(9) 0.48976(18) 0.86470(9) 0.0436(4) Uani d . 1
C C15 0.65938(10) 0.4277(2) 0.86667(12) 0.0596(6) Uani d . 1
C C16 0.60208(11) 0.4993(2) 0.85812(13) 0.0667(6) Uani d . 1
C C17 0.60088(11) 0.6368(2) 0.84824(11) 0.0589(5) Uani d . 1
C C18 0.65601(11) 0.6988(2) 0.84519(11) 0.0586(5) Uani d . 1
C C19 0.71301(11) 0.6250(2) 0.85320(10) 0.0525(5) Uani d . 1
C C20 0.85865(19) -0.0622(3) 0.97519(18) 0.0957(10) Uani d . 1
C C21 0.80938(19) -0.1530(3) 0.98260(16) 0.0963(10) Uani d . 1
C C22 0.89018(18) 0.1465(3) 0.83444(15) 0.0930(9) Uani d . 1
C C23 0.90252(16) 0.0103(4) 0.81830(16) 0.0989(10) Uani d . 1
C C24 0.54361(16) 0.8430(3) 0.84361(19) 0.1038(12) Uani d . 1
H H6 1.0276 0.7404 0.9401 0.083 Uiso calc R 1
H H21 0.7610 0.2782 0.9357 0.053 Uiso calc R 1
H H31 0.7679 0.3463 0.8355 0.049 Uiso calc R 1
H H81 0.9632 0.6325 0.9862 0.058 Uiso calc R 1
H H101 0.7706 0.4525 0.7514 0.065 Uiso calc R 1
H H111 0.7983 0.5257 0.6674 0.074 Uiso calc R 1
H H121 0.8960 0.6395 0.6832 0.076 Uiso calc R 1
H H131 0.9646 0.6994 0.7848 0.068 Uiso calc R 1
H H151 0.6601 0.3230 0.8750 0.071 Uiso calc R 1
H H161 0.5596 0.4502 0.8591 0.080 Uiso calc R 1
H H181 0.6553 0.7910 0.8377 0.070 Uiso calc R 1
H H191 0.7487 0.6669 0.8508 0.063 Uiso calc R 1
H H201 0.9030 -0.0639 1.0173 0.115 Uiso calc R 1
H H202 0.8708 -0.0913 0.9351 0.115 Uiso calc R 1
H H211 0.7686 -0.1586 0.9396 0.116 Uiso calc R 1
H H212 0.7941 -0.1177 1.0185 0.116 Uiso calc R 1
H H213 0.8303 -0.2473 0.9950 0.116 Uiso calc R 1
H H221 0.9333 0.1881 0.8636 0.112 Uiso calc R 1
H H222 0.8721 0.2019 0.7940 0.112 Uiso calc R 1
H H231 0.8583 -0.0365 0.7950 0.119 Uiso calc R 1
H H232 0.9286 -0.0405 0.8593 0.119 Uiso calc R 1
H H233 0.9293 0.0130 0.7894 0.119 Uiso calc R 1
H H241 0.5474 0.8736 0.8060 0.125 Uiso calc R 1
H H242 0.5793 0.8740 0.8787 0.125 Uiso calc R 1
H H243 0.5042 0.8741 0.8460 0.125 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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
_geom_angle_publ_flag
O4 P O5 114.48(10) y
O4 P O3 115.74(11) y
O5 P O3 104.43(11) y
O4 P C2 114.36(9) y
O5 P C2 106.37(9) y
O3 P C2 99.90(9) y
C1 O1 C9 120.89(15) n
C20 O3 P 122.52(17) n
C22 O5 P 125.35(18) n
C7 O6 H6 109.5 ?
C17 O7 C24 117.9(2) ?
O2 C1 O1 118.05(18) ?
O2 C1 C2 125.32(18) ?
O1 C1 C2 116.61(16) ?
C1 C2 C3 111.81(15) ?
C1 C2 P 107.75(13) ?
C3 C2 P 113.78(13) ?
C1 C2 H21 107.8 ?
C3 C2 H21 107.8 ?
P C2 H21 107.8 ?
C4 C3 C14 113.67(15) ?
C4 C3 C2 107.47(15) ?
C14 C3 C2 111.86(15) ?
C4 C3 H31 107.9 ?
C14 C3 H31 107.9 ?
C2 C3 H31 107.9 ?
C9 C4 C5 117.07(17) ?
C9 C4 C3 118.56(16) ?
C5 C4 C3 124.35(16) ?
C6 C5 C10 117.40(18) ?
C6 C5 C4 120.10(17) ?
C10 C5 C4 122.48(18) ?
C13 C6 C5 119.73(19) ?
C13 C6 C7 121.19(19) ?
C5 C6 C7 119.08(17) ?
O6 C7 C8 123.23(19) ?
O6 C7 C6 116.41(18) ?
C8 C7 C6 120.37(18) ?
C7 C8 C9 119.15(19) ?
C7 C8 H81 120.4 ?
C9 C8 H81 120.4 ?
C4 C9 C8 124.20(17) ?
C4 C9 O1 121.96(17) ?
C8 C9 O1 113.77(16) ?
C11 C10 C5 121.0(2) ?
C11 C10 H101 119.5 ?
C5 C10 H101 119.5 ?
C10 C11 C12 120.7(2) ?
C10 C11 H111 119.7 ?
C12 C11 H111 119.7 ?
C13 C12 C11 120.2(2) ?
C13 C12 H121 119.9 ?
C11 C12 H121 119.9 ?
C12 C13 C6 120.9(2) ?
C12 C13 H131 119.6 ?
C6 C13 H131 119.6 ?
C19 C14 C15 117.34(18) ?
C19 C14 C3 122.67(17) ?
C15 C14 C3 119.98(17) ?
C16 C15 C14 121.5(2) ?
C16 C15 H151 119.3 ?
C14 C15 H151 119.3 ?
C15 C16 C17 119.8(2) ?
C15 C16 H161 120.1 ?
C17 C16 H161 120.1 ?
O7 C17 C18 124.5(2) ?
O7 C17 C16 116.0(2) ?
C18 C17 C16 119.4(2) ?
C17 C18 C19 120.0(2) ?
C17 C18 H181 120.0 ?
C19 C18 H181 120.0 ?
C14 C19 C18 121.9(2) ?
C14 C19 H191 119.0 ?
C18 C19 H191 119.0 ?
O3 C20 C21 107.4(3) ?
O3 C20 H201 110.2 ?
C21 C20 H201 110.2 ?
O3 C20 H202 110.2 ?
C21 C20 H202 110.2 ?
H201 C20 H202 108.5 ?
C20 C21 H211 109.5 ?
C20 C21 H212 109.5 ?
H211 C21 H212 109.5 ?
C20 C21 H213 109.5 ?
H211 C21 H213 109.5 ?
H212 C21 H213 109.5 ?
O5 C22 C23 110.2(3) ?
O5 C22 H221 109.6 ?
C23 C22 H221 109.6 ?
O5 C22 H222 109.6 ?
C23 C22 H222 109.6 ?
H221 C22 H222 108.1 ?
C22 C23 H231 109.5 ?
C22 C23 H232 109.5 ?
H231 C23 H232 109.5 ?
C22 C23 H233 109.5 ?
H231 C23 H233 109.5 ?
H232 C23 H233 109.5 ?
O7 C24 H241 109.5 ?
O7 C24 H242 109.5 ?
H241 C24 H242 109.5 ?
O7 C24 H243 109.5 ?
H241 C24 H243 109.5 ?
H242 C24 H243 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P O4 1.4524(15) y
P O5 1.5449(17) y
P O3 1.5551(16) y
P C2 1.8248(19) y
O1 C1 1.356(2) y
O1 C9 1.404(2) y
O2 C1 1.194(2) y
O3 C20 1.449(3) y
O5 C22 1.450(3) y
O6 C7 1.352(2) y
O6 H6 0.8309 ?
O7 C17 1.367(3) ?
O7 C24 1.420(3) ?
C1 C2 1.509(3) ?
C2 C3 1.551(3) ?
C2 H21 0.9241 ?
C3 C4 1.515(2) ?
C3 C14 1.528(3) ?
C3 H31 1.0001 ?
C4 C9 1.366(3) ?
C4 C5 1.428(3) ?
C5 C6 1.419(3) ?
C5 C10 1.422(3) ?
C6 C13 1.415(3) ?
C6 C7 1.425(3) ?
C7 C8 1.360(3) ?
C8 C9 1.397(3) ?
C8 H81 0.8711 ?
C10 C11 1.374(3) ?
C10 H101 0.9613 ?
C11 C12 1.392(3) ?
C11 H111 0.9082 ?
C12 C13 1.357(3) ?
C12 H121 0.9322 ?
C13 H131 0.9462 ?
C14 C19 1.374(3) ?
C14 C15 1.394(3) ?
C15 C16 1.381(3) ?
C15 H151 1.0672 ?
C16 C17 1.391(3) ?
C16 H161 1.0483 ?
C17 C18 1.368(3) ?
C18 C19 1.390(3) ?
C18 H181 0.9346 ?
C19 H191 0.8967 ?
C20 C21 1.455(4) ?
C20 H201 1.0668 ?
C20 H202 1.0668 ?
C21 H211 1.0385 ?
C21 H212 1.0385 ?
C21 H213 1.0385 ?
C22 C23 1.459(4) ?
C22 H221 1.0092 ?
C22 H222 1.0092 ?
C23 H231 1.0166 ?
C23 H232 1.0166 ?
C23 H233 1.0166 ?
C24 H241 0.9270 ?
C24 H242 0.9270 ?
C24 H243 0.9270 ?
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
_geom_hbond_publ_flag
O6 H6 O4 5_767 0.83 1.87 2.701(2) 178 y
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
_geom_torsion_publ_flag
O4 P C2 C1 -28.73(16) y
O5 P C2 C3 -31.54(16) y
O4 P O3 C20 -58.5(3) ?
O5 P O3 C20 68.3(3) ?
C2 P O3 C20 178.2(2) ?
O4 P O5 C22 -3.4(3) ?
O3 P O5 C22 -131.0(2) ?
C2 P O5 C22 123.9(2) ?
C9 O1 C1 O2 179.21(17) ?
C9 O1 C1 C2 0.5(2) ?
O2 C1 C2 C3 143.09(19) ?
O1 C1 C2 C3 -38.3(2) ?
O2 C1 C2 P -91.2(2) ?
O1 C1 C2 P 87.41(17) ?
O5 P C2 C1 -156.12(13) ?
O3 P C2 C1 95.53(15) ?
O4 P C2 C3 95.84(15) ?
O5 P C2 C3 -31.54(16) ?
O3 P C2 C3 -139.90(15) ?
C1 C2 C3 C4 52.53(19) ?
P C2 C3 C4 -69.83(17) ?
C1 C2 C3 C14 -72.89(19) ?
P C2 C3 C14 164.74(12) ?
C14 C3 C4 C9 90.9(2) ?
C2 C3 C4 C9 -33.4(2) ?
C14 C3 C4 C5 -87.6(2) ?
C2 C3 C4 C5 148.11(17) ?
C9 C4 C5 C6 1.9(3) ?
C3 C4 C5 C6 -179.65(16) ?
C9 C4 C5 C10 -176.39(17) ?
C3 C4 C5 C10 2.1(3) ?
C10 C5 C6 C13 -2.8(3) ?
C4 C5 C6 C13 178.90(17) ?
C10 C5 C6 C7 176.76(17) ?
C4 C5 C6 C7 -1.6(3) ?
C13 C6 C7 O6 0.0(3) ?
C5 C6 C7 O6 -179.46(17) ?
C13 C6 C7 C8 179.94(18) ?
C5 C6 C7 C8 0.4(3) ?
O6 C7 C8 C9 -179.72(18) ?
C6 C7 C8 C9 0.4(3) ?
C5 C4 C9 C8 -1.1(3) ?
C3 C4 C9 C8 -179.64(17) ?
C5 C4 C9 O1 175.78(15) ?
C3 C4 C9 O1 -2.8(3) ?
C7 C8 C9 C4 -0.1(3) ?
C7 C8 C9 O1 -177.13(17) ?
C1 O1 C9 C4 22.1(3) ?
C1 O1 C9 C8 -160.77(17) ?
C6 C5 C10 C11 1.8(3) ?
C4 C5 C10 C11 -179.95(18) ?
C5 C10 C11 C12 1.1(3) ?
C10 C11 C12 C13 -3.0(3) ?
C11 C12 C13 C6 1.9(3) ?
C5 C6 C13 C12 1.0(3) ?
C7 C6 C13 C12 -178.5(2) ?
C4 C3 C14 C19 8.2(3) ?
C2 C3 C14 C19 130.13(19) ?
C4 C3 C14 C15 -173.41(18) ?
C2 C3 C14 C15 -51.5(2) ?
C19 C14 C15 C16 -0.7(3) ?
C3 C14 C15 C16 -179.2(2) ?
C14 C15 C16 C17 -1.0(4) ?
C24 O7 C17 C18 -7.7(4) ?
C24 O7 C17 C16 170.6(3) ?
C15 C16 C17 O7 -176.4(2) ?
C15 C16 C17 C18 2.0(4) ?
O7 C17 C18 C19 177.0(2) ?
C16 C17 C18 C19 -1.3(4) ?
C15 C14 C19 C18 1.4(3) ?
C3 C14 C19 C18 179.84(19) ?
C17 C18 C19 C14 -0.4(3) ?
P O3 C20 C21 -162.7(2) ?
P O5 C22 C23 114.1(3) ?
