#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:32:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180304 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/18/7151821.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_7151821
loop_
_publ_author_name
'Wu, Yan-Chao'
'Li, Hui-Jing'
'Liu, Li'
'Liu, Zhe'
'Wang, Dong'
'Chen, Yong-Jun'
_publ_section_title
;
 Cascade reaction of β,γ-unsaturated α-ketoesters with phenols in
 trityl chloride/TFA system. Highly selective synthesis of
 4-aryl-2H-chromenes and their applications.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2868
_journal_page_last               2877
_journal_paper_doi               10.1039/c0ob01143f
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C21 H22 O4'
_chemical_formula_weight         338.39
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.567(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.3688(8)
_cell_length_b                   7.7163(4)
_cell_length_c                   18.1469(11)
_cell_measurement_temperature    293(2)
_cell_volume                     1871.15(18)
_computing_cell_refinement       'RAPID AUTO (Rigaku, 2001)'
_computing_data_collection       'RAPID AUTO (Rigaku, 2001)'
_computing_data_reduction        'RAPID AUTO (Rigaku, 2001)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1994)'
_computing_publication_material  'SHELXTL (Siemens, 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Rigaku R-axis RAPID IP'
_diffrn_measurement_method       Oscillation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1574
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3958
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9733
_exptl_absorpt_correction_T_min  0.9382
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Psi scan'
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.73
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.673
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.673
_refine_ls_R_factor_all          0.1399
_refine_ls_R_factor_gt           0.0521
_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)+(0.0600P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1338
_reflns_number_gt                1238
_reflns_number_total             3958
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob01143f.txt
_cod_data_source_block           3a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Empirical' changed to 'empirical'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7151821
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.00143(17) 0.6975(3) 0.04171(13) 0.0825(7) Uani 1 1 d . . .
O2 O 0.01757(15) 0.8291(3) 0.15401(11) 0.0715(6) Uani 1 1 d . . .
O3 O -0.03921(14) 0.3926(2) 0.09552(11) 0.0664(6) Uani 1 1 d . . .
H3A H -0.0143 0.4030 0.0617 0.100 Uiso 1 1 calc R . .
O4 O 0.09379(13) 0.4988(2) 0.20233(11) 0.0595(5) Uani 1 1 d . . .
C1 C 0.0354(3) 0.9936(3) 0.1217(2) 0.0907(11) Uani 1 1 d . . .
H1A H 0.0444 1.0837 0.1602 0.136 Uiso 1 1 calc R . .
H1B H -0.0209 1.0209 0.0746 0.136 Uiso 1 1 calc R . .
H1C H 0.0945 0.9845 0.1091 0.136 Uiso 1 1 calc R . .
C2 C 0.00377(19) 0.6941(4) 0.10773(18) 0.0540(7) Uani 1 1 d . . .
C3 C -0.0075(2) 0.5268(3) 0.14920(16) 0.0498(7) Uani 1 1 d . . .
C4 C -0.07650(18) 0.5382(3) 0.19410(15) 0.0497(7) Uani 1 1 d . . .
H4B H -0.1309 0.6132 0.1765 0.060 Uiso 1 1 calc R . .
C5 C -0.06151(18) 0.4436(3) 0.25843(16) 0.0464(7) Uani 1 1 d . . .
C6 C -0.13240(18) 0.4527(3) 0.30064(17) 0.0475(7) Uani 1 1 d . . .
C7 C -0.2350(2) 0.4439(4) 0.25856(19) 0.0635(8) Uani 1 1 d . . .
H7A H -0.2594 0.4204 0.2045 0.076 Uiso 1 1 calc R . .
C8 C -0.3012(2) 0.4705(4) 0.2977(2) 0.0790(10) Uani 1 1 d . . .
H8A H -0.3697 0.4645 0.2691 0.095 Uiso 1 1 calc R . .
C9 C -0.2684(3) 0.5045(4) 0.3760(2) 0.0807(10) Uani 1 1 d . . .
H9A H -0.3137 0.5236 0.4009 0.097 Uiso 1 1 calc R . .
C10 C -0.1675(3) 0.5106(4) 0.41835(19) 0.0753(9) Uani 1 1 d . . .
H10A H -0.1439 0.5333 0.4725 0.090 Uiso 1 1 calc R . .
C11 C -0.1005(2) 0.4833(3) 0.38090(17) 0.0603(8) Uani 1 1 d . . .
H11A H -0.0322 0.4856 0.4107 0.072 Uiso 1 1 calc R . .
C12 C 0.02982(18) 0.3381(3) 0.28822(15) 0.0466(7) Uani 1 1 d . . .
C13 C 0.1055(2) 0.3706(3) 0.25910(16) 0.0521(7) Uani 1 1 d . . .
C14 C 0.1948(2) 0.2825(4) 0.28588(17) 0.0649(8) Uani 1 1 d . . .
H14A H 0.2456 0.3115 0.2679 0.078 Uiso 1 1 calc R . .
C15 C 0.2080(2) 0.1497(4) 0.34008(17) 0.0646(8) Uani 1 1 d . . .
H15A H 0.2682 0.0895 0.3582 0.078 Uiso 1 1 calc R . .
C16 C 0.13300(19) 0.1039(4) 0.36827(16) 0.0534(7) Uani 1 1 d . . .
C17 C 0.04555(18) 0.2015(3) 0.34197(15) 0.0519(7) Uani 1 1 d . . .
H17A H -0.0046 0.1747 0.3610 0.062 Uiso 1 1 calc R . .
C18 C 0.1461(2) -0.0501(4) 0.42421(17) 0.0608(8) Uani 1 1 d . . .
C19 C 0.2255(5) -0.1708(7) 0.4213(4) 0.272(4) Uani 1 1 d . . .
H19A H 0.2312 -0.2661 0.4567 0.408 Uiso 1 1 calc R . .
H19B H 0.2882 -0.1104 0.4369 0.408 Uiso 1 1 calc R . .
H19C H 0.2082 -0.2139 0.3683 0.408 Uiso 1 1 calc R . .
C20 C 0.0546(3) -0.1486(6) 0.4054(3) 0.211(3) Uani 1 1 d . . .
H20A H 0.0655 -0.2432 0.4420 0.317 Uiso 1 1 calc R . .
H20B H 0.0347 -0.1930 0.3525 0.317 Uiso 1 1 calc R . .
H20C H 0.0028 -0.0749 0.4094 0.317 Uiso 1 1 calc R . .
C21 C 0.1772(4) 0.0115(5) 0.5062(2) 0.194(3) Uani 1 1 d . . .
H21A H 0.1842 -0.0855 0.5409 0.291 Uiso 1 1 calc R . .
H21D H 0.1276 0.0896 0.5108 0.291 Uiso 1 1 calc R . .
H21B H 0.2401 0.0708 0.5204 0.291 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 C1 116.3(2) . . ?
C3 O3 H3A 109.5 . . ?
C13 O4 C3 114.84(19) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 124.9(3) . . ?
O1 C2 C3 123.1(3) . . ?
O2 C2 C3 112.0(2) . . ?
O3 C3 O4 110.6(2) . . ?
O3 C3 C4 108.4(2) . . ?
O4 C3 C4 110.7(2) . . ?
O3 C3 C2 110.6(2) . . ?
O4 C3 C2 101.1(2) . . ?
C4 C3 C2 115.3(2) . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 H4B 119.3 . . ?
C3 C4 H4B 119.3 . . ?
C4 C5 C12 117.6(2) . . ?
C4 C5 C6 120.6(2) . . ?
C12 C5 C6 121.7(2) . . ?
C11 C6 C7 117.6(3) . . ?
C11 C6 C5 122.0(2) . . ?
C7 C6 C5 120.3(3) . . ?
C6 C7 C8 119.8(3) . . ?
C6 C7 H7A 120.1 . . ?
C8 C7 H7A 120.1 . . ?
C9 C8 C7 121.7(3) . . ?
C9 C8 H8A 119.2 . . ?
C7 C8 H8A 119.2 . . ?
C8 C9 C10 119.1(3) . . ?
C8 C9 H9A 120.4 . . ?
C10 C9 H9A 120.4 . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C6 C11 C10 121.6(3) . . ?
C6 C11 H11A 119.2 . . ?
C10 C11 H11A 119.2 . . ?
C13 C12 C17 116.8(2) . . ?
C13 C12 C5 118.5(2) . . ?
C17 C12 C5 124.7(2) . . ?
C14 C13 O4 117.2(2) . . ?
C14 C13 C12 122.3(3) . . ?
O4 C13 C12 120.6(2) . . ?
C13 C14 C15 119.0(3) . . ?
C13 C14 H14A 120.5 . . ?
C15 C14 H14A 120.5 . . ?
C14 C15 C16 121.7(3) . . ?
C14 C15 H15A 119.2 . . ?
C16 C15 H15A 119.2 . . ?
C17 C16 C15 117.3(3) . . ?
C17 C16 C18 121.6(3) . . ?
C15 C16 C18 121.1(2) . . ?
C16 C17 C12 122.8(3) . . ?
C16 C17 H17A 118.6 . . ?
C12 C17 H17A 118.6 . . ?
C20 C18 C21 108.7(4) . . ?
C20 C18 C19 107.7(4) . . ?
C21 C18 C19 106.7(4) . . ?
C20 C18 C16 111.9(3) . . ?
C21 C18 C16 109.8(3) . . ?
C19 C18 C16 111.8(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21D 109.5 . . ?
H21A C21 H21D 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21D C21 H21B 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.186(3) . ?
O2 C2 1.307(3) . ?
O2 C1 1.460(3) . ?
O3 C3 1.379(3) . ?
O3 H3A 0.8200 . ?
O4 C13 1.393(3) . ?
O4 C3 1.436(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.532(4) . ?
C3 C4 1.500(3) . ?
C4 C5 1.325(3) . ?
C4 H4B 0.9300 . ?
C5 C12 1.468(3) . ?
C5 C6 1.484(3) . ?
C6 C11 1.377(3) . ?
C6 C7 1.390(3) . ?
C7 C8 1.397(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.347(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.370(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.383(4) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.395(3) . ?
C12 C17 1.397(3) . ?
C13 C14 1.373(3) . ?
C14 C15 1.384(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.397(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.390(3) . ?
C16 C18 1.529(4) . ?
C17 H17A 0.9300 . ?
C18 C20 1.447(4) . ?
C18 C21 1.466(4) . ?
C18 C19 1.489(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21D 0.9600 . ?
C21 H21B 0.9600 . ?
