#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/42/4024297.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_4024297
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            'C16 H20 O5'
_chemical_formula_weight         292.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.2119(4)
_cell_length_b                   9.6137(4)
_cell_length_c                   38.6588(18)
_cell_measurement_reflns_used    7846
_cell_measurement_temperature    180(1)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.70
_cell_volume                     3052.0(2)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      180(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       Omega
_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  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            18787
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Plate fragment'
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.960
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.960
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0783
_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)+(0.0270P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1282
_reflns_number_gt                3289
_reflns_number_total             3781
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802311w_si_006.cif
_cod_data_source_block           ef1347m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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      Pbca
_cod_database_code               4024297
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 0.35025(15) 0.44212(12) 0.21774(3) 0.0282(3) Uani 1 1 d . . .
C2 C 0.2191(2) 0.54039(17) 0.21303(4) 0.0263(4) Uani 1 1 d . . .
O3 O 0.27110(15) 0.64598(12) 0.18865(3) 0.0278(3) Uani 1 1 d . . .
C4 C 0.3598(2) 0.61114(18) 0.16045(4) 0.0256(4) Uani 1 1 d . . .
C5 C 0.3930(2) 0.45663(17) 0.15561(4) 0.0232(4) Uani 1 1 d . . .
H5 H 0.2850 0.4138 0.1502 0.028 Uiso 1 1 calc R . .
C6 C 0.4421(2) 0.39804(18) 0.19073(5) 0.0266(4) Uani 1 1 d . . .
C7 C 0.2021(2) 0.61347(18) 0.24728(5) 0.0307(4) Uani 1 1 d . . .
H7X H 0.1806 0.5448 0.2655 0.046 Uiso 1 1 calc R . .
H7Y H 0.1114 0.6796 0.2461 0.046 Uiso 1 1 calc R . .
H7Z H 0.3030 0.6635 0.2526 0.046 Uiso 1 1 calc R . .
C8 C 0.0632(2) 0.47052(19) 0.20142(5) 0.0318(4) Uani 1 1 d . . .
H8X H 0.0834 0.4186 0.1800 0.048 Uiso 1 1 calc R . .
H8Y H -0.0204 0.5413 0.1973 0.048 Uiso 1 1 calc R . .
H8Z H 0.0258 0.4064 0.2195 0.048 Uiso 1 1 calc R . .
O9 O 0.40543(16) 0.70323(13) 0.14184(3) 0.0346(3) Uani 1 1 d . . .
O10 O 0.55259(15) 0.32050(13) 0.19656(3) 0.0332(3) Uani 1 1 d . . .
C11 C 0.5044(2) 0.42030(19) 0.12465(5) 0.0305(4) Uani 1 1 d . . .
C12 C 0.4299(2) 0.48329(19) 0.09144(5) 0.0303(4) Uani 1 1 d . . .
C13 C 0.2765(3) 0.4426(2) 0.07999(5) 0.0381(5) Uani 1 1 d . . .
H13 H 0.2148 0.3790 0.0935 0.046 Uiso 1 1 calc R . .
C14 C 0.2118(3) 0.4924(2) 0.04939(5) 0.0440(5) Uani 1 1 d . . .
H14 H 0.1062 0.4638 0.0423 0.053 Uiso 1 1 calc R . .
C15 C 0.3001(3) 0.5838(2) 0.02909(5) 0.0405(5) Uani 1 1 d . . .
C16 C 0.4511(3) 0.6267(2) 0.04010(5) 0.0438(5) Uani 1 1 d . . .
H16 H 0.5126 0.6903 0.0265 0.053 Uiso 1 1 calc R . .
C17 C 0.5133(3) 0.5771(2) 0.07102(5) 0.0400(5) Uani 1 1 d . . .
H17 H 0.6172 0.6087 0.0784 0.048 Uiso 1 1 calc R . .
O18 O 0.2292(2) 0.62424(17) -0.00159(4) 0.0555(4) Uani 1 1 d . . .
C19 C 0.3270(4) 0.7076(3) -0.02396(6) 0.0661(8) Uani 1 1 d . . .
H19X H 0.3434 0.7994 -0.0135 0.099 Uiso 1 1 calc R . .
H19Y H 0.2721 0.7182 -0.0463 0.099 Uiso 1 1 calc R . .
H19Z H 0.4328 0.6625 -0.0274 0.099 Uiso 1 1 calc R . .
C20 C 0.5094(3) 0.2609(2) 0.11990(5) 0.0389(5) Uani 1 1 d . . .
H20X H 0.5548 0.2176 0.1407 0.058 Uiso 1 1 calc R . .
H20Y H 0.5779 0.2378 0.0999 0.058 Uiso 1 1 calc R . .
H20Z H 0.3988 0.2259 0.1160 0.058 Uiso 1 1 calc R . .
C21 C 0.6797(2) 0.4729(2) 0.13163(6) 0.0438(5) Uani 1 1 d . . .
H21X H 0.6777 0.5738 0.1354 0.066 Uiso 1 1 calc R . .
H21Y H 0.7490 0.4515 0.1117 0.066 Uiso 1 1 calc R . .
H21Z H 0.7232 0.4269 0.1523 0.066 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
C6 O1 C2 121.49(13) . . ?
O1 C2 O3 108.70(13) . . ?
O1 C2 C7 105.32(14) . . ?
O3 C2 C7 105.82(13) . . ?
O1 C2 C8 112.19(14) . . ?
O3 C2 C8 111.51(14) . . ?
C7 C2 C8 112.89(15) . . ?
C4 O3 C2 120.59(13) . . ?
O9 C4 O3 117.90(16) . . ?
O9 C4 C5 126.19(16) . . ?
O3 C4 C5 115.91(14) . . ?
C4 C5 C6 107.38(14) . . ?
C4 C5 C11 114.92(14) . . ?
C6 C5 C11 116.72(14) . . ?
O10 C6 O1 118.16(16) . . ?
O10 C6 C5 126.79(17) . . ?
O1 C6 C5 115.04(14) . . ?
C20 C11 C12 107.51(15) . . ?
C20 C11 C5 109.38(15) . . ?
C12 C11 C5 108.68(14) . . ?
C20 C11 C21 108.66(16) . . ?
C12 C11 C21 112.62(16) . . ?
C5 C11 C21 109.92(15) . . ?
C17 C12 C13 116.82(18) . . ?
C17 C12 C11 122.30(18) . . ?
C13 C12 C11 120.83(17) . . ?
C14 C13 C12 121.51(19) . . ?
C13 C14 C15 120.3(2) . . ?
C16 C15 O18 124.3(2) . . ?
C16 C15 C14 119.23(19) . . ?
O18 C15 C14 116.5(2) . . ?
C15 C16 C17 119.8(2) . . ?
C12 C17 C16 122.4(2) . . ?
C15 O18 C19 116.26(19) . . ?
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 C6 1.356(2) . ?
O1 C2 1.444(2) . ?
C2 O3 1.450(2) . ?
C2 C7 1.506(2) . ?
C2 C8 1.514(2) . ?
O3 C4 1.353(2) . ?
C4 O9 1.201(2) . ?
C4 C5 1.522(2) . ?
C5 C6 1.524(2) . ?
C5 C11 1.547(2) . ?
C6 O10 1.196(2) . ?
C11 C20 1.544(3) . ?
C11 C12 1.546(3) . ?
C11 C21 1.549(3) . ?
C12 C17 1.380(3) . ?
C12 C13 1.391(3) . ?
C13 C14 1.383(3) . ?
C14 C15 1.383(3) . ?
C15 C16 1.374(3) . ?
C15 O18 1.377(2) . ?
C16 C17 1.385(3) . ?
O18 C19 1.427(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658881
