#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/43/4024305.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_4024305
loop_
_publ_author_name
'Eric Fillion'
'Ashraf Wilsily'
'Dan Fishlock'
_publ_section_title
;
Probing Persistent Intramolecular C-H...X (X = O, S, Br, Cl, and F)
Bonding in Solution Using Benzyl Meldrum's Acid Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1259
_journal_page_last               1267
_journal_paper_doi               10.1021/jo802311w
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C20 H26 O6'
_chemical_formula_weight         362.41
_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                 97.923(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.017(3)
_cell_length_b                   12.411(5)
_cell_length_c                   18.403(7)
_cell_measurement_temperature    180(2)
_cell_volume                     1813.6(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13217
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.9733
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'APEX II'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0032(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.396
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.396
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0556
_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)+(0.0020P)²+0.9654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1257
_reflns_number_gt                3101
_reflns_number_total             4241
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802311w_si_014.cif
_cod_data_source_block           aw-2-257c_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2_1/n
_cod_database_code               4024305
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
O20 O 0.91045(19) 0.46604(12) 0.14076(8) 0.0314(4) Uani 1 1 d . . .
O18 O 0.7054(2) 0.40827(14) 0.02007(10) 0.0441(5) Uani 1 1 d . . .
O1 O 0.8365(2) 0.30460(12) 0.34759(9) 0.0360(4) Uani 1 1 d . . .
O3 O 1.0322(2) 0.43524(13) 0.39529(9) 0.0385(4) Uani 1 1 d . . .
O10 O 0.9120(2) 0.18748(12) 0.26876(10) 0.0399(4) Uani 1 1 d . . .
O9 O 1.2848(2) 0.42852(14) 0.36381(10) 0.0411(4) Uani 1 1 d . . .
C5 C 1.0544(3) 0.36076(16) 0.27555(12) 0.0258(4) Uani 1 1 d . . .
H5 H 0.9837 0.4184 0.2514 0.031 Uiso 1 1 calc R . .
C17 C 0.9324(3) 0.36548(17) 0.11058(12) 0.0284(5) Uani 1 1 d . . .
C11 C 1.1676(3) 0.32430(16) 0.21787(12) 0.0276(5) Uani 1 1 d . . .
C26 C 1.2814(3) 0.41915(17) 0.19961(13) 0.0327(5) Uani 1 1 d . . .
H26X H 1.2111 0.4758 0.1754 0.039 Uiso 1 1 calc R . .
H26Y H 1.3401 0.4484 0.2449 0.039 Uiso 1 1 calc R . .
C12 C 1.0494(3) 0.29290(17) 0.14735(12) 0.0280(5) Uani 1 1 d . . .
C16 C 0.8243(3) 0.33414(19) 0.04775(13) 0.0346(5) Uani 1 1 d . . .
C6 C 0.9305(3) 0.27542(17) 0.29479(12) 0.0299(5) Uani 1 1 d . . .
C4 C 1.1391(3) 0.40998(17) 0.34642(13) 0.0322(5) Uani 1 1 d . . .
C22 C 1.2837(3) 0.23143(18) 0.25021(14) 0.0344(5) Uani 1 1 d . . .
H22X H 1.3326 0.2514 0.2995 0.041 Uiso 1 1 calc R . .
H22Y H 1.2147 0.1680 0.2541 0.041 Uiso 1 1 calc R . .
C13 C 1.0543(3) 0.18965(18) 0.11717(14) 0.0350(5) Uani 1 1 d . . .
H13 H 1.1277 0.1388 0.1409 0.042 Uiso 1 1 calc R . .
C2 C 0.8547(3) 0.40984(19) 0.38064(14) 0.0376(6) Uani 1 1 d . . .
C7 C 0.7567(3) 0.49464(19) 0.33335(14) 0.0394(6) Uani 1 1 d . . .
H7X H 0.7981 0.4988 0.2869 0.059 Uiso 1 1 calc R . .
H7Y H 0.7703 0.5633 0.3575 0.059 Uiso 1 1 calc R . .
H7Z H 0.6395 0.4756 0.3256 0.059 Uiso 1 1 calc R . .
C25 C 1.4096(3) 0.3849(2) 0.15062(15) 0.0436(6) Uani 1 1 d . . .
H25X H 1.4757 0.4468 0.1397 0.052 Uiso 1 1 calc R . .
H25Y H 1.3517 0.3571 0.1047 0.052 Uiso 1 1 calc R . .
C14 C 0.9540(3) 0.16145(19) 0.05366(15) 0.0428(6) Uani 1 1 d . . .
H14 H 0.9635 0.0929 0.0343 0.051 Uiso 1 1 calc R . .
C15 C 0.8392(3) 0.2329(2) 0.01807(14) 0.0418(6) Uani 1 1 d . . .
H15 H 0.7727 0.2132 -0.0253 0.050 Uiso 1 1 calc R . .
C21 C 0.9351(3) 0.55824(19) 0.09574(14) 0.0438(6) Uani 1 1 d . . .
H21X H 0.9165 0.6231 0.1219 0.066 Uiso 1 1 calc R . .
H21Y H 0.8571 0.5552 0.0513 0.066 Uiso 1 1 calc R . .
H21Z H 1.0482 0.5579 0.0840 0.066 Uiso 1 1 calc R . .
C23 C 1.4268(3) 0.2010(2) 0.20699(16) 0.0430(6) Uani 1 1 d . . .
H23X H 1.5020 0.1510 0.2358 0.052 Uiso 1 1 calc R . .
H23Y H 1.3800 0.1648 0.1620 0.052 Uiso 1 1 calc R . .
C24 C 1.5260(3) 0.2983(2) 0.18821(17) 0.0473(7) Uani 1 1 d . . .
H24X H 1.6062 0.2767 0.1560 0.057 Uiso 1 1 calc R . .
H24Y H 1.5887 0.3275 0.2327 0.057 Uiso 1 1 calc R . .
C8 C 0.7961(4) 0.3989(2) 0.45434(16) 0.0547(8) Uani 1 1 d . . .
H8X H 0.8614 0.3445 0.4824 0.082 Uiso 1 1 calc R . .
H8Y H 0.6794 0.3788 0.4479 0.082 Uiso 1 1 calc R . .
H8Z H 0.8100 0.4665 0.4799 0.082 Uiso 1 1 calc R . .
C19 C 0.5800(4) 0.3722(3) -0.03729(16) 0.0588(8) Uani 1 1 d . . .
H19X H 0.5039 0.4303 -0.0523 0.088 Uiso 1 1 calc R . .
H19Y H 0.5186 0.3134 -0.0199 0.088 Uiso 1 1 calc R . .
H19Z H 0.6329 0.3487 -0.0783 0.088 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
C17 O20 C21 116.66(18) . . ?
C16 O18 C19 116.6(2) . . ?
C6 O1 C2 120.64(17) . . ?
C4 O3 C2 121.28(18) . . ?
C4 C5 C6 108.01(18) . . ?
C4 C5 C11 118.06(18) . . ?
C6 C5 C11 114.56(17) . . ?
O20 C17 C16 118.8(2) . . ?
O20 C17 C12 119.82(19) . . ?
C16 C17 C12 121.0(2) . . ?
C12 C11 C22 113.65(18) . . ?
C12 C11 C26 108.61(18) . . ?
C22 C11 C26 107.90(17) . . ?
C12 C11 C5 107.33(17) . . ?
C22 C11 C5 109.31(18) . . ?
C26 C11 C5 110.01(17) . . ?
C25 C26 C11 112.45(19) . . ?
C13 C12 C17 116.7(2) . . ?
C13 C12 C11 121.1(2) . . ?
C17 C12 C11 122.23(18) . . ?
O18 C16 C15 123.8(2) . . ?
O18 C16 C17 116.1(2) . . ?
C15 C16 C17 120.1(2) . . ?
O10 C6 O1 118.7(2) . . ?
O10 C6 C5 126.2(2) . . ?
O1 C6 C5 115.08(18) . . ?
O9 C4 O3 117.5(2) . . ?
O9 C4 C5 128.1(2) . . ?
O3 C4 C5 114.42(19) . . ?
C23 C22 C11 116.0(2) . . ?
C14 C13 C12 121.8(2) . . ?
O1 C2 O3 108.47(17) . . ?
O1 C2 C8 105.9(2) . . ?
O3 C2 C8 105.9(2) . . ?
O1 C2 C7 111.9(2) . . ?
O3 C2 C7 112.0(2) . . ?
C8 C2 C7 112.3(2) . . ?
C26 C25 C24 110.5(2) . . ?
C13 C14 C15 121.1(2) . . ?
C14 C15 C16 119.1(2) . . ?
C24 C23 C22 112.2(2) . . ?
C23 C24 C25 111.0(2) . . ?
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
O20 C17 1.387(2) . ?
O20 C21 1.442(3) . ?
O18 C16 1.371(3) . ?
O18 C19 1.426(3) . ?
O1 C6 1.359(2) . ?
O1 C2 1.440(3) . ?
O3 C4 1.362(3) . ?
O3 C2 1.446(3) . ?
O10 C6 1.193(3) . ?
O9 C4 1.190(3) . ?
C5 C4 1.514(3) . ?
C5 C6 1.526(3) . ?
C5 C11 1.556(3) . ?
C17 C16 1.401(3) . ?
C17 C12 1.405(3) . ?
C11 C12 1.548(3) . ?
C11 C22 1.548(3) . ?
C11 C26 1.554(3) . ?
C26 C25 1.519(3) . ?
C12 C13 1.399(3) . ?
C16 C15 1.382(3) . ?
C22 C23 1.531(3) . ?
C13 C14 1.370(4) . ?
C2 C8 1.502(3) . ?
C2 C7 1.515(3) . ?
C25 C24 1.525(4) . ?
C14 C15 1.376(4) . ?
C23 C24 1.513(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658885
