#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:08:27 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178422 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/43/4024303.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_4024303
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_moiety         'C19 H22 O5'
_chemical_formula_sum            'C19 H22 O5'
_chemical_formula_weight         330.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.029(5)
_cell_angle_beta                 100.953(6)
_cell_angle_gamma                100.439(6)
_cell_formula_units_Z            2
_cell_length_a                   6.0581(5)
_cell_length_b                   9.1995(10)
_cell_length_c                   15.9090(17)
_cell_measurement_reflns_used    2917
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.6
_cell_volume                     851.03(15)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0104
_diffrn_reflns_av_sigmaI/netI    0.0778
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2917
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.019
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0851
_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)+(0.0971P)²+0.9439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2371
_refine_ls_wR_factor_ref         0.2538
_reflns_number_gt                2122
_reflns_number_total             2917
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo802311w_si_012.cif
_cod_data_source_block           k08204
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               4024303
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.7448(6) 0.1142(3) 0.5663(2) 0.0533(8) Uani 1 1 d . . .
O3 O 1.0394(5) 0.3087(4) 0.5519(2) 0.0520(8) Uani 1 1 d . . .
O9 O 1.3103(5) 0.3877(4) 0.6675(2) 0.0575(9) Uani 1 1 d . . .
O10 O 0.7290(6) 0.0406(3) 0.6940(2) 0.0579(9) Uani 1 1 d . . .
O18 O 0.8557(5) 0.5818(3) 0.7315(2) 0.0540(9) Uani 1 1 d . . .
C2 C 0.8059(8) 0.2309(5) 0.5151(3) 0.0519(11) Uani 1 1 d . . .
C4 C 1.1107(8) 0.3357(5) 0.6387(3) 0.0460(10) Uani 1 1 d . . .
C5 C 0.9267(7) 0.2947(4) 0.6896(3) 0.0408(10) Uani 1 1 d . . .
H5 H 0.8171 0.3626 0.6745 0.049 Uiso 1 1 calc R . .
C6 C 0.7930(8) 0.1404(5) 0.6547(3) 0.0469(11) Uani 1 1 d . . .
C7 C 0.8181(10) 0.1559(7) 0.4288(3) 0.0685(15) Uani 1 1 d . . .
H7X H 0.9345 0.0938 0.4370 0.103 Uiso 1 1 calc R . .
H7Y H 0.8594 0.2316 0.3911 0.103 Uiso 1 1 calc R . .
H7Z H 0.6685 0.0935 0.4023 0.103 Uiso 1 1 calc R . .
C8 C 0.6369(9) 0.3352(6) 0.5066(3) 0.0633(14) Uani 1 1 d . . .
H8X H 0.6414 0.3856 0.5634 0.095 Uiso 1 1 calc R . .
H8Y H 0.4818 0.2780 0.4829 0.095 Uiso 1 1 calc R . .
H8Z H 0.6784 0.4093 0.4680 0.095 Uiso 1 1 calc R . .
C11 C 1.0091(7) 0.3233(4) 0.7900(3) 0.0406(10) Uani 1 1 d . . .
C12 C 1.1476(7) 0.4828(5) 0.8169(3) 0.0426(10) Uani 1 1 d . . .
C13 C 1.3558(7) 0.5101(5) 0.8749(3) 0.0450(10) Uani 1 1 d . . .
H13 H 1.4162 0.4280 0.8957 0.054 Uiso 1 1 calc R . .
C14 C 1.4801(8) 0.6532(5) 0.9040(3) 0.0528(12) Uani 1 1 d . . .
H14 H 1.6226 0.6677 0.9438 0.063 Uiso 1 1 calc R . .
C15 C 1.3956(9) 0.7732(5) 0.8750(3) 0.0561(12) Uani 1 1 d . . .
H15 H 1.4799 0.8712 0.8945 0.067 Uiso 1 1 calc R . .
C16 C 1.1866(8) 0.7516(5) 0.8171(3) 0.0529(12) Uani 1 1 d . . .
H16 H 1.1278 0.8346 0.7971 0.063 Uiso 1 1 calc R . .
C17 C 1.0639(8) 0.6083(5) 0.7886(3) 0.0446(10) Uani 1 1 d . . .
C19 C 0.7371(9) 0.7017(5) 0.7176(3) 0.0548(12) Uani 1 1 d . . .
H19X H 0.5772 0.6620 0.6889 0.082 Uiso 1 1 calc R . .
H19Y H 0.8111 0.7684 0.6812 0.082 Uiso 1 1 calc R . .
H19Z H 0.7418 0.7569 0.7731 0.082 Uiso 1 1 calc R . .
C20 C 0.7954(7) 0.3059(5) 0.8308(3) 0.0452(10) Uani 1 1 d . . .
H20X H 0.7213 0.3925 0.8212 0.054 Uiso 1 1 calc R . .
H20Y H 0.6838 0.2154 0.8026 0.054 Uiso 1 1 calc R . .
C21 C 0.8601(8) 0.2946(5) 0.9269(3) 0.0503(11) Uani 1 1 d . . .
H21X H 0.9767 0.3831 0.9548 0.060 Uiso 1 1 calc R . .
H21Y H 0.7231 0.2921 0.9526 0.060 Uiso 1 1 calc R . .
C22 C 0.9550(8) 0.1552(5) 0.9427(3) 0.0529(12) Uani 1 1 d . . .
H22X H 1.0293 0.1608 1.0043 0.063 Uiso 1 1 calc R . .
H22Y H 0.8275 0.0675 0.9296 0.063 Uiso 1 1 calc R . .
C23 C 1.1258(8) 0.1368(5) 0.8882(3) 0.0497(11) Uani 1 1 d . . .
H23 H 1.2223 0.0678 0.9029 0.060 Uiso 1 1 calc R . .
C24 C 1.1518(8) 0.2096(5) 0.8211(3) 0.0460(11) Uani 1 1 d . . .
H24 H 1.2654 0.1901 0.7905 0.055 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 120.5(3) . . ?
C4 O3 C2 119.7(3) . . ?
C17 O18 C19 118.8(3) . . ?
O1 C2 O3 108.7(4) . . ?
O1 C2 C7 106.4(4) . . ?
O3 C2 C7 104.9(4) . . ?
O1 C2 C8 111.9(4) . . ?
O3 C2 C8 112.2(4) . . ?
C7 C2 C8 112.3(5) . . ?
O9 C4 O3 118.2(4) . . ?
O9 C4 C5 126.6(4) . . ?
O3 C4 C5 115.2(4) . . ?
C4 C5 C6 108.4(3) . . ?
C4 C5 C11 115.4(3) . . ?
C6 C5 C11 115.8(4) . . ?
O10 C6 O1 117.5(4) . . ?
O10 C6 C5 128.2(4) . . ?
O1 C6 C5 114.2(4) . . ?
C24 C11 C12 110.9(4) . . ?
C24 C11 C20 109.4(4) . . ?
C12 C11 C20 108.0(3) . . ?
C24 C11 C5 109.5(3) . . ?
C12 C11 C5 110.6(3) . . ?
C20 C11 C5 108.3(3) . . ?
C13 C12 C17 116.7(4) . . ?
C13 C12 C11 120.9(4) . . ?
C17 C12 C11 122.3(4) . . ?
C12 C13 C14 122.5(4) . . ?
C15 C14 C13 119.6(5) . . ?
C14 C15 C16 120.0(4) . . ?
C17 C16 C15 119.9(4) . . ?
O18 C17 C16 121.8(4) . . ?
O18 C17 C12 116.9(4) . . ?
C16 C17 C12 121.3(4) . . ?
C21 C20 C11 110.9(4) . . ?
C22 C21 C20 110.3(4) . . ?
C23 C22 C21 111.3(4) . . ?
C24 C23 C22 124.6(4) . . ?
C23 C24 C11 123.5(4) . . ?
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 1.375(6) . ?
O1 C2 1.430(6) . ?
O3 C4 1.357(5) . ?
O3 C2 1.455(6) . ?
O9 C4 1.204(6) . ?
O10 C6 1.195(5) . ?
O18 C17 1.378(5) . ?
O18 C19 1.429(5) . ?
C2 C7 1.514(7) . ?
C2 C8 1.520(7) . ?
C4 C5 1.508(6) . ?
C5 C6 1.510(6) . ?
C5 C11 1.569(6) . ?
C11 C24 1.525(6) . ?
C11 C12 1.539(6) . ?
C11 C20 1.543(6) . ?
C12 C13 1.385(6) . ?
C12 C17 1.410(6) . ?
C13 C14 1.391(6) . ?
C14 C15 1.371(7) . ?
C15 C16 1.389(7) . ?
C16 C17 1.389(6) . ?
C20 C21 1.520(6) . ?
C21 C22 1.515(6) . ?
C22 C23 1.495(7) . ?
C23 C24 1.318(7) . ?
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_site_symmetry_A
C19 H19A O9 0.98 2.70 3.442(6) 132.9 1_455
