#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/43/4024306.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_4024306
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            'C23 H28 O6'
_chemical_formula_weight         400.45
_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                 110.720(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3229(7)
_cell_length_b                   9.9293(5)
_cell_length_c                   16.8309(9)
_cell_measurement_reflns_used    4820
_cell_measurement_temperature    180(1)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.42
_cell_volume                     2082.50(19)
_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 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12701
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Rhombic plate'
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0101(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.356
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         5050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.356
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0489
_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)+(0.0100P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0774
_reflns_number_gt                3232
_reflns_number_total             5050
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802311w_si_015.cif
_cod_data_source_block           ef1351m
_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.

'_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      P2(1)/n
_cod_database_code               4024306
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 0.67500(8) 0.71036(10) 0.23814(7) 0.0392(3) Uani 1 1 d . . .
C2 C 0.73641(12) 0.58790(15) 0.25050(11) 0.0352(4) Uani 1 1 d . . .
O3 O 0.66812(8) 0.47964(10) 0.20559(6) 0.0346(3) Uani 1 1 d . . .
C4 C 0.56778(12) 0.46515(15) 0.20707(9) 0.0312(4) Uani 1 1 d . . .
C5 C 0.52747(11) 0.57637(14) 0.25023(9) 0.0291(4) Uani 1 1 d . . .
H5 H 0.5626 0.5571 0.3123 0.035 Uiso 1 1 calc R . .
C6 C 0.57357(12) 0.71109(16) 0.23818(10) 0.0346(4) Uani 1 1 d . . .
C7 C 0.81587(12) 0.60933(15) 0.20675(11) 0.0458(5) Uani 1 1 d . . .
H7X H 0.8580 0.5270 0.2108 0.069 Uiso 1 1 calc R . .
H7Y H 0.8640 0.6838 0.2341 0.069 Uiso 1 1 calc R . .
H7Z H 0.7775 0.6312 0.1468 0.069 Uiso 1 1 calc R . .
C8 C 0.78945(13) 0.55525(17) 0.34321(10) 0.0492(5) Uani 1 1 d . . .
H8X H 0.7346 0.5451 0.3691 0.074 Uiso 1 1 calc R . .
H8Y H 0.8385 0.6283 0.3716 0.074 Uiso 1 1 calc R . .
H8Z H 0.8299 0.4710 0.3494 0.074 Uiso 1 1 calc R . .
O9 O 0.51901(8) 0.36581(10) 0.17535(7) 0.0403(3) Uani 1 1 d . . .
O10 O 0.52847(8) 0.81793(10) 0.22978(8) 0.0459(3) Uani 1 1 d . . .
C11 C 0.40490(11) 0.57295(15) 0.23466(9) 0.0301(4) Uani 1 1 d . . .
C12 C 0.33095(11) 0.59372(14) 0.14091(9) 0.0282(3) Uani 1 1 d . . .
C13 C 0.36449(12) 0.61653(14) 0.07194(10) 0.0301(4) Uani 1 1 d . . .
C14 C 0.29365(12) 0.62768(14) -0.01127(10) 0.0349(4) Uani 1 1 d . . .
H14 H 0.3200 0.6396 -0.0564 0.042 Uiso 1 1 calc R . .
C15 C 0.18535(13) 0.62137(15) -0.02779(10) 0.0397(4) Uani 1 1 d . . .
H15 H 0.1365 0.6293 -0.0846 0.048 Uiso 1 1 calc R . .
C16 C 0.14700(13) 0.60367(15) 0.03717(10) 0.0385(4) Uani 1 1 d . . .
H16 H 0.0719 0.6011 0.0256 0.046 Uiso 1 1 calc R . .
C17 C 0.21873(12) 0.58953(14) 0.12000(10) 0.0331(4) Uani 1 1 d . . .
O18 O 0.47331(8) 0.62493(10) 0.08889(7) 0.0388(3) Uani 1 1 d . . .
C19 C 0.51033(13) 0.69308(18) 0.03011(11) 0.0554(5) Uani 1 1 d . . .
H19X H 0.4935 0.6392 -0.0218 0.083 Uiso 1 1 calc R . .
H19Y H 0.5881 0.7061 0.0555 0.083 Uiso 1 1 calc R . .
H19Z H 0.4748 0.7809 0.0161 0.083 Uiso 1 1 calc R . .
O20 O 0.18362(8) 0.57125(11) 0.18639(7) 0.0438(3) Uani 1 1 d . . .
C21 C 0.07230(12) 0.56408(17) 0.17074(11) 0.0487(5) Uani 1 1 d . . .
H21X H 0.0384 0.6497 0.1468 0.073 Uiso 1 1 calc R . .
H21Y H 0.0607 0.5464 0.2241 0.073 Uiso 1 1 calc R . .
H21Z H 0.0406 0.4912 0.1304 0.073 Uiso 1 1 calc R . .
C22 C 0.38314(12) 0.68271(16) 0.29263(10) 0.0394(4) Uani 1 1 d . . .
H22X H 0.3771 0.7709 0.2652 0.059 Uiso 1 1 calc R . .
H22Y H 0.4426 0.6843 0.3474 0.059 Uiso 1 1 calc R . .
H22Z H 0.3161 0.6620 0.3018 0.059 Uiso 1 1 calc R . .
C23 C 0.38117(12) 0.43424(15) 0.26713(10) 0.0403(4) Uani 1 1 d . . .
H23X H 0.3119 0.4380 0.2752 0.060 Uiso 1 1 calc R . .
H23Y H 0.4379 0.4128 0.3213 0.060 Uiso 1 1 calc R . .
H23Z H 0.3788 0.3644 0.2253 0.060 Uiso 1 1 calc R . .
C24 C 0.33935(16) 0.1176(3) 0.08341(13) 0.0679(6) Uani 1 1 d . . .
H24 H 0.4139 0.1279 0.1145 0.081 Uiso 1 1 calc R . .
C25 C 0.28008(19) 0.2247(2) 0.04859(14) 0.0614(6) Uani 1 1 d . . .
H25 H 0.3128 0.3110 0.0553 0.074 Uiso 1 1 calc R . .
C26 C 0.17641(19) 0.2130(2) 0.00485(13) 0.0694(6) Uani 1 1 d . . .
H26 H 0.1358 0.2909 -0.0194 0.083 Uiso 1 1 calc R . .
C27 C 0.12777(18) 0.0933(4) -0.00591(14) 0.0863(9) Uani 1 1 d . . .
H27 H 0.0532 0.0865 -0.0378 0.104 Uiso 1 1 calc R . .
C28 C 0.1857(3) -0.0202(3) 0.02927(19) 0.1022(12) Uani 1 1 d . . .
H28 H 0.1523 -0.1061 0.0225 0.123 Uiso 1 1 calc R . .
C29 C 0.2941(3) -0.0052(3) 0.07475(16) 0.0880(9) Uani 1 1 d . . .
H29 H 0.3365 -0.0815 0.0998 0.106 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 121.45(12) . . ?
O3 C2 O1 109.51(11) . . ?
O3 C2 C8 111.23(13) . . ?
O1 C2 C8 111.52(13) . . ?
O3 C2 C7 105.82(12) . . ?
O1 C2 C7 105.81(13) . . ?
C8 C2 C7 112.65(13) . . ?
C4 O3 C2 121.00(11) . . ?
O9 C4 O3 117.57(14) . . ?
O9 C4 C5 125.69(14) . . ?
O3 C4 C5 116.73(13) . . ?
C6 C5 C4 110.41(12) . . ?
C6 C5 C11 116.52(12) . . ?
C4 C5 C11 115.45(12) . . ?
O10 C6 O1 117.56(14) . . ?
O10 C6 C5 125.81(15) . . ?
O1 C6 C5 116.62(13) . . ?
C12 C11 C23 109.91(12) . . ?
C12 C11 C22 110.65(12) . . ?
C23 C11 C22 107.08(12) . . ?
C12 C11 C5 114.74(12) . . ?
C23 C11 C5 106.92(12) . . ?
C22 C11 C5 107.18(12) . . ?
C13 C12 C17 114.74(14) . . ?
C13 C12 C11 126.18(13) . . ?
C17 C12 C11 119.08(13) . . ?
O18 C13 C14 119.60(14) . . ?
O18 C13 C12 117.31(13) . . ?
C14 C13 C12 123.08(14) . . ?
C15 C14 C13 119.46(15) . . ?
C14 C15 C16 120.41(15) . . ?
C15 C16 C17 119.62(15) . . ?
O20 C17 C16 121.34(14) . . ?
O20 C17 C12 116.03(14) . . ?
C16 C17 C12 122.62(15) . . ?
C13 O18 C19 118.88(12) . . ?
C17 O20 C21 119.61(13) . . ?
C25 C24 C29 120.2(2) . . ?
C26 C25 C24 121.0(2) . . ?
C25 C26 C27 121.1(2) . . ?
C26 C27 C28 120.0(2) . . ?
C27 C28 C29 117.8(2) . . ?
C24 C29 C28 119.9(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
O1 C6 1.3516(16) . ?
O1 C2 1.4389(17) . ?
C2 O3 1.4382(16) . ?
C2 C8 1.503(2) . ?
C2 C7 1.503(2) . ?
O3 C4 1.3534(17) . ?
C4 O9 1.1979(16) . ?
C4 C5 1.5204(19) . ?
C5 C6 1.515(2) . ?
C5 C11 1.5600(19) . ?
C6 O10 1.2027(16) . ?
C11 C12 1.5502(19) . ?
C11 C23 1.5549(19) . ?
C11 C22 1.5569(19) . ?
C12 C13 1.402(2) . ?
C12 C17 1.4102(19) . ?
C13 O18 1.3776(16) . ?
C13 C14 1.389(2) . ?
C14 C15 1.3709(19) . ?
C15 C16 1.372(2) . ?
C16 C17 1.391(2) . ?
C17 O20 1.3676(17) . ?
O18 C19 1.4230(17) . ?
O20 C21 1.4134(16) . ?
C24 C25 1.331(3) . ?
C24 C29 1.346(3) . ?
C25 C26 1.320(3) . ?
C26 C27 1.335(3) . ?
C27 C28 1.376(3) . ?
C28 C29 1.382(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658886
