#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/97/2209737.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_2209737
loop_
_publ_author_name
'Da-Quan Peng'
_publ_section_title
4-Butyl-2-phenyl-2-(trimethylsilyloxy)-3,4-dihydro-2H,5H-pyrano[3,2-c][1]benzopyran-5-one
_journal_coeditor_code           AT2061
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3572
_journal_page_last               o3573
_journal_paper_doi               10.1107/S1600536806028686
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C25 H30 O4 Si'
_chemical_formula_moiety         'C25 H30 O4 Si'
_chemical_formula_sum            'C25 H30 O4 Si'
_chemical_formula_weight         422.58
_chemical_melting_point          389.2
_chemical_name_systematic
;
4-Butyl-2-phenyl-2-(trimethylsilyloxy)-3,4-dihydro-2H,5H-
pyrano[3,2-c][1]benzopyran-5-one
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 90.20(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.138(2)
_cell_length_b                   12.874(3)
_cell_length_c                   15.300(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     2390.8(8)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0783
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4420
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XCAD4; Harms & Wocadlo, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.35
_refine_ls_extinction_coef       0.0192(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0603
_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)+(0.0463P)²+1.79P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1538
_reflns_number_gt                2484
_reflns_number_total             4208
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2061.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2209737
_cod_database_fobs_code          2209737
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_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
O O1 0.31524(15) 0.35280(16) 0.37902(13) 0.0530(6) Uani d . 1
O O2 0.38656(16) 0.20111(17) 0.43653(13) 0.0551(6) Uani d . 1
O O3 -0.02571(19) 0.2168(2) 0.27937(17) 0.0780(8) Uani d . 1
O O4 -0.01687(17) 0.3763(2) 0.32973(15) 0.0662(7) Uani d . 1
C C1 0.1766(6) -0.0827(5) 0.5075(4) 0.163 Uani d . 1
H H1A 0.1453 -0.1435 0.5339 0.244 Uiso calc R 1
H H1B 0.1305 -0.0238 0.5192 0.244 Uiso calc R 1
H H1C 0.2488 -0.0706 0.5313 0.244 Uiso calc R 1
C C2 0.1843(6) -0.0973(4) 0.4182(4) 0.155(3) Uani d . 1
H H2A 0.1106 -0.1118 0.3967 0.186 Uiso calc R 1
H H2B 0.2276 -0.1596 0.4089 0.186 Uiso calc R 1
C C3 0.2323(4) -0.0132(3) 0.3609(3) 0.0876(13) Uani d . 1
H H3A 0.3103 -0.0064 0.3737 0.105 Uiso calc R 1
H H3B 0.2250 -0.0338 0.3001 0.105 Uiso calc R 1
C C4 0.1782(3) 0.0894(3) 0.3732(2) 0.0656(10) Uani d . 1
H H4A 0.1992 0.1162 0.4301 0.079 Uiso calc R 1
H H4B 0.0991 0.0789 0.3737 0.079 Uiso calc R 1
C C5 0.2052(2) 0.1727(3) 0.3037(2) 0.0547(8) Uani d . 1
H H5 0.1743 0.1489 0.2479 0.066 Uiso calc R 1
C C6 0.3277(2) 0.1963(3) 0.2888(2) 0.0549(8) Uani d . 1
H H6A 0.3673 0.1311 0.2836 0.066 Uiso calc R 1
H H6B 0.3354 0.2333 0.2340 0.066 Uiso calc R 1
C C7 0.3804(2) 0.2601(3) 0.3608(2) 0.0514(8) Uani d . 1
C C8 0.2791(3) 0.2880(4) 0.5860(3) 0.0943(14) Uani d . 1
H H8A 0.2615 0.3525 0.5578 0.141 Uiso calc R 1
H H8B 0.2885 0.2993 0.6476 0.141 Uiso calc R 1
H H8C 0.2204 0.2393 0.5765 0.141 Uiso calc R 1
C C9 0.4452(4) 0.1116(3) 0.5922(3) 0.0910(14) Uani d . 1
H H9A 0.3861 0.0628 0.5850 0.136 Uiso calc R 1
H H9B 0.4586 0.1228 0.6534 0.136 Uiso calc R 1
H H9C 0.5107 0.0846 0.5654 0.136 Uiso calc R 1
C C10 0.5174(4) 0.3332(4) 0.5508(3) 0.1016(15) Uani d . 1
H H10A 0.4948 0.3966 0.5229 0.152 Uiso calc R 1
H H10B 0.5833 0.3079 0.5235 0.152 Uiso calc R 1
H H10C 0.5317 0.3462 0.6116 0.152 Uiso calc R 1
C C11 0.4935(2) 0.3022(3) 0.3343(2) 0.0581(9) Uani d . 1
C C12 0.5092(3) 0.4015(3) 0.3041(3) 0.0753(11) Uani d . 1
H H12 0.4491 0.4460 0.2996 0.090 Uiso calc R 1
C C13 0.6122(4) 0.4367(4) 0.2803(3) 0.1034(15) Uani d . 1
H H13 0.6215 0.5043 0.2603 0.124 Uiso calc R 1
C C14 0.7001(4) 0.3710(6) 0.2863(3) 0.1095(19) Uani d . 1
H H14 0.7697 0.3941 0.2700 0.131 Uiso calc R 1
C C15 0.6874(3) 0.2729(5) 0.3157(3) 0.1055(18) Uani d . 1
H H15 0.7485 0.2296 0.3203 0.127 Uiso calc R 1
C C16 0.5830(3) 0.2356(4) 0.3394(2) 0.0827(13) Uani d . 1
H H16 0.5740 0.1674 0.3582 0.099 Uiso calc R 1
C C17 0.2050(2) 0.3529(3) 0.36205(18) 0.0467(8) Uani d . 1
C C18 0.1500(2) 0.2730(3) 0.32634(19) 0.0485(8) Uani d . 1
C C19 0.0324(3) 0.2835(3) 0.3100(2) 0.0571(9) Uani d . 1
C C20 0.0399(2) 0.4571(3) 0.3666(2) 0.0547(9) Uani d . 1
C C21 -0.0177(3) 0.5462(3) 0.3865(2) 0.0686(10) Uani d . 1
H H21 -0.0920 0.5516 0.3723 0.082 Uiso calc R 1
C C22 0.0346(3) 0.6261(3) 0.4271(3) 0.0763(11) Uani d . 1
H H22 -0.0044 0.6862 0.4404 0.092 Uiso calc R 1
C C23 0.1447(3) 0.6193(3) 0.4487(3) 0.0705(10) Uani d . 1
H H23 0.1794 0.6740 0.4775 0.085 Uiso calc R 1
C C24 0.2031(3) 0.5317(3) 0.4275(2) 0.0592(9) Uani d . 1
H H24 0.2778 0.5280 0.4409 0.071 Uiso calc R 1
C C25 0.1520(2) 0.4487(3) 0.38645(19) 0.0481(8) Uani d . 1
Si Si 0.40752(7) 0.23564(8) 0.54003(6) 0.0574(3) Uani d . 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'
Si Si 0.0817 0.0704 '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
C17 O1 C7 119.8(2) yes
C7 O2 Si 131.0(2) yes
C20 O4 C19 122.3(2) yes
C2 C1 H1A 109.5 ?
C2 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
C2 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
C1 C2 C3 120.2(5) ?
C1 C2 H2A 107.3 ?
C3 C2 H2A 107.3 ?
C1 C2 H2B 107.3 ?
C3 C2 H2B 107.3 ?
H2A C2 H2B 106.9 ?
C4 C3 C2 113.0(4) ?
C4 C3 H3A 109.0 ?
C2 C3 H3A 109.0 ?
C4 C3 H3B 109.0 ?
C2 C3 H3B 109.0 ?
H3A C3 H3B 107.8 ?
C3 C4 C5 115.7(3) ?
C3 C4 H4A 108.4 ?
C5 C4 H4A 108.4 ?
C3 C4 H4B 108.4 ?
C5 C4 H4B 108.4 ?
H4A C4 H4B 107.4 ?
C18 C5 C6 107.4(3) ?
C18 C5 C4 110.0(3) ?
C6 C5 C4 116.5(3) ?
C18 C5 H5 107.5 ?
C6 C5 H5 107.5 ?
C4 C5 H5 107.5 ?
C7 C6 C5 114.0(2) yes
C7 C6 H6A 108.7 ?
C5 C6 H6A 108.7 ?
C7 C6 H6B 108.7 ?
C5 C6 H6B 108.7 ?
H6A C6 H6B 107.6 ?
O2 C7 O1 108.4(2) ?
O2 C7 C6 109.4(3) ?
O1 C7 C6 110.8(2) ?
O2 C7 C11 111.7(2) ?
O1 C7 C11 104.4(3) ?
C6 C7 C11 112.1(2) ?
Si C8 H8A 109.5 ?
Si C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
Si C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
Si C9 H9A 109.5 ?
Si C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
Si C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
Si C10 H10A 109.5 ?
Si C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
Si C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
C12 C11 C16 119.0(3) ?
C12 C11 C7 123.0(3) ?
C16 C11 C7 118.0(4) ?
C11 C12 C13 121.5(4) ?
C11 C12 H12 119.3 ?
C13 C12 H12 119.3 ?
C14 C13 C12 119.2(5) ?
C14 C13 H13 120.4 ?
C12 C13 H13 120.4 ?
C15 C14 C13 120.8(5) ?
C15 C14 H14 119.6 ?
C13 C14 H14 119.6 ?
C14 C15 C16 120.7(5) ?
C14 C15 H15 119.7 ?
C16 C15 H15 119.7 ?
C11 C16 C15 118.8(5) ?
C11 C16 H16 120.6 ?
C15 C16 H16 120.6 ?
C18 C17 O1 124.3(3) ?
C18 C17 C25 122.7(3) ?
O1 C17 C25 112.9(3) ?
C17 C18 C19 119.0(3) ?
C17 C18 C5 122.3(3) ?
C19 C18 C5 118.7(3) ?
O3 C19 O4 116.9(3) ?
O3 C19 C18 124.9(3) ?
O4 C19 C18 118.2(3) ?
O4 C20 C21 118.0(3) ?
O4 C20 C25 121.3(3) ?
C21 C20 C25 120.7(3) ?
C22 C21 C20 119.7(3) ?
C22 C21 H21 120.1 ?
C20 C21 H21 120.1 ?
C21 C22 C23 120.8(4) ?
C21 C22 H22 119.6 ?
C23 C22 H22 119.6 ?
C24 C23 C22 119.8(4) ?
C24 C23 H23 120.1 ?
C22 C23 H23 120.1 ?
C23 C24 C25 120.7(3) ?
C23 C24 H24 119.6 ?
C25 C24 H24 119.6 ?
C24 C25 C20 118.3(3) ?
C24 C25 C17 125.4(3) ?
C20 C25 C17 116.4(3) ?
O2 Si C8 109.55(16) ?
O2 Si C10 112.09(16) ?
C8 Si C10 109.3(2) ?
O2 Si C9 102.59(15) ?
C8 Si C9 111.2(2) ?
C10 Si C9 112.0(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C17 1.362(3) ?
O1 C7 1.459(4) ?
O2 C7 1.387(4) yes
O2 Si 1.664(2) yes
O3 C19 1.205(4) yes
O4 C20 1.368(4) ?
O4 C19 1.369(4) ?
C1 C2 1.382(7) ?
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 C3 1.512(6) ?
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
C3 C4 1.487(5) ?
C3 H3A 0.9700 ?
C3 H3B 0.9700 ?
C4 C5 1.546(5) ?
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C5 C18 1.496(4) ?
C5 C6 1.535(4) ?
C5 H5 0.9800 ?
C6 C7 1.514(4) ?
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C7 C11 1.532(4) yes
C8 Si 1.840(4) ?
C8 H8A 0.9600 ?
C8 H8B 0.9600 ?
C8 H8C 0.9600 ?
C9 Si 1.842(4) ?
C9 H9A 0.9600 ?
C9 H9B 0.9600 ?
C9 H9C 0.9600 ?
C10 Si 1.840(4) ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
C11 C12 1.373(5) ?
C11 C16 1.385(5) ?
C12 C13 1.379(5) ?
C12 H12 0.9300 ?
C13 C14 1.365(7) ?
C13 H13 0.9300 ?
C14 C15 1.349(7) ?
C14 H14 0.9300 ?
C15 C16 1.405(6) ?
C15 H15 0.9300 ?
C16 H16 0.9300 ?
C17 C18 1.341(4) ?
C17 C25 1.441(4) ?
C18 C19 1.455(4) ?
C20 C21 1.378(5) ?
C20 C25 1.398(4) ?
C21 C22 1.357(5) ?
C21 H21 0.9300 ?
C22 C23 1.379(5) ?
C22 H22 0.9300 ?
C23 C24 1.371(5) ?
C23 H23 0.9300 ?
C24 C25 1.384(4) ?
C24 H24 0.9300 ?
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_publ_flag
C4 H4A O2 0.97 2.52 3.064(4) 115 yes
C12 H12 O1 0.93 2.36 2.696(4) 101 yes
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
C1 C2 C3 C4 -53.4(8)
C2 C3 C4 C5 -167.4(4)
C3 C4 C5 C18 -177.2(3)
C3 C4 C5 C6 -54.8(4)
C18 C5 C6 C7 49.2(4)
C4 C5 C6 C7 -74.7(4)
Si O2 C7 O1 -42.7(3)
Si O2 C7 C6 -163.5(2)
Si O2 C7 C11 71.8(3)
C17 O1 C7 O2 -93.6(3)
C17 O1 C7 C6 26.4(4)
C17 O1 C7 C11 147.2(2)
C5 C6 C7 O2 68.4(3)
C5 C6 C7 O1 -51.1(4)
C5 C6 C7 C11 -167.2(3)
O2 C7 C11 C12 -138.4(3)
O1 C7 C11 C12 -21.5(4)
C6 C7 C11 C12 98.4(4)
O2 C7 C11 C16 43.2(4)
O1 C7 C11 C16 160.1(3)
C6 C7 C11 C16 -80.0(4)
C16 C11 C12 C13 -1.1(6)
C7 C11 C12 C13 -179.6(3)
C11 C12 C13 C14 0.5(7)
C12 C13 C14 C15 -0.4(8)
C13 C14 C15 C16 1.0(8)
C12 C11 C16 C15 1.7(5)
C7 C11 C16 C15 -179.8(3)
C14 C15 C16 C11 -1.7(7)
C7 O1 C17 C18 -2.1(4)
C7 O1 C17 C25 178.0(2)
O1 C17 C18 C19 -178.9(3)
C25 C17 C18 C19 1.0(4)
O1 C17 C18 C5 1.9(5)
C25 C17 C18 C5 -178.2(3)
C6 C5 C18 C17 -25.0(4)
C4 C5 C18 C17 102.7(3)
C6 C5 C18 C19 155.7(3)
C4 C5 C18 C19 -76.5(3)
C20 O4 C19 O3 178.5(3)
C20 O4 C19 C18 -2.2(4)
C17 C18 C19 O3 -179.0(3)
C5 C18 C19 O3 0.3(5)
C17 C18 C19 O4 1.8(4)
C5 C18 C19 O4 -179.0(3)
C19 O4 C20 C21 -178.0(3)
C19 O4 C20 C25 -0.2(4)
O4 C20 C21 C22 176.8(3)
C25 C20 C21 C22 -1.0(5)
C20 C21 C22 C23 0.0(6)
C21 C22 C23 C24 1.3(6)
C22 C23 C24 C25 -1.6(5)
C23 C24 C25 C20 0.5(5)
C23 C24 C25 C17 -179.4(3)
O4 C20 C25 C24 -177.0(3)
C21 C20 C25 C24 0.8(4)
O4 C20 C25 C17 2.9(4)
C21 C20 C25 C17 -179.3(3)
C18 C17 C25 C24 176.5(3)
O1 C17 C25 C24 -3.6(4)
C18 C17 C25 C20 -3.4(4)
O1 C17 C25 C20 176.6(2)
C7 O2 Si C8 78.3(3)
C7 O2 Si C10 -43.2(3)
C7 O2 Si C9 -163.5(3)
