#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/42/4024293.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_4024293
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            'C15 H18 O6'
_chemical_formula_weight         294.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 104.548(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4134(14)
_cell_length_b                   20.429(4)
_cell_length_c                   9.8491(19)
_cell_measurement_reflns_used    7261
_cell_measurement_temperature    180(1)
_cell_measurement_theta_max      30.08
_cell_measurement_theta_min      2.36
_cell_volume                     1443.8(5)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10218
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0168(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   2.156
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.156
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0414
_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          0.0756
_refine_ls_wR_factor_ref         0.0765
_reflns_number_gt                2942
_reflns_number_total             3431
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802311w_si_002.cif
_cod_data_source_block           ef1233m
_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)/c
_cod_database_code               4024293
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 -0.09587(11) 0.34272(4) 0.19206(8) 0.0321(2) Uani 1 1 d . . .
C2 C -0.10484(16) 0.38311(6) 0.07043(13) 0.0303(3) Uani 1 1 d . . .
O3 O 0.08006(11) 0.39409(4) 0.05158(9) 0.0332(2) Uani 1 1 d . . .
C4 C 0.20933(17) 0.34573(6) 0.07502(13) 0.0299(3) Uani 1 1 d . . .
C5 C 0.15490(16) 0.28165(6) 0.12927(12) 0.0262(3) Uani 1 1 d . . .
C6 C 0.02051(16) 0.29109(6) 0.22044(12) 0.0282(3) Uani 1 1 d . . .
C7 C -0.17131(19) 0.44900(6) 0.10741(15) 0.0440(4) Uani 1 1 d . . .
H7X H -0.2994 0.4451 0.1169 0.066 Uiso 1 1 calc R . .
H7Y H -0.1677 0.4805 0.0331 0.066 Uiso 1 1 calc R . .
H7Z H -0.0901 0.4642 0.1963 0.066 Uiso 1 1 calc R . .
C8 C -0.22927(17) 0.35264(6) -0.05820(13) 0.0348(3) Uani 1 1 d . . .
H8X H -0.1789 0.3099 -0.0752 0.052 Uiso 1 1 calc R . .
H8Y H -0.2356 0.3812 -0.1392 0.052 Uiso 1 1 calc R . .
H8Z H -0.3546 0.3469 -0.0441 0.052 Uiso 1 1 calc R . .
O9 O 0.35875(12) 0.35695(4) 0.05361(10) 0.0435(3) Uani 1 1 d . . .
O10 O 0.01025(11) 0.25505(4) 0.31442(9) 0.0383(2) Uani 1 1 d . . .
C11 C 0.32291(16) 0.23906(6) 0.20185(13) 0.0327(3) Uani 1 1 d . . .
H11X H 0.4211 0.2679 0.2579 0.039 Uiso 1 1 calc R . .
H11Y H 0.2835 0.2090 0.2678 0.039 Uiso 1 1 calc R . .
C12 C 0.40620(16) 0.19901(5) 0.10411(12) 0.0277(3) Uani 1 1 d . . .
C13 C 0.58487(17) 0.21152(6) 0.08895(14) 0.0362(3) Uani 1 1 d . . .
H13 H 0.6540 0.2472 0.1378 0.043 Uiso 1 1 calc R . .
C14 C 0.66261(17) 0.17282(6) 0.00409(14) 0.0393(3) Uani 1 1 d . . .
H14 H 0.7849 0.1820 -0.0044 0.047 Uiso 1 1 calc R . .
C15 C 0.56452(17) 0.12078(6) -0.06889(14) 0.0360(3) Uani 1 1 d . . .
H15 H 0.6188 0.0944 -0.1276 0.043 Uiso 1 1 calc R . .
C16 C 0.38620(16) 0.10734(5) -0.05571(13) 0.0299(3) Uani 1 1 d . . .
C17 C 0.30872(15) 0.14640(5) 0.03191(12) 0.0262(3) Uani 1 1 d . . .
O18 O 0.27609(11) 0.05700(4) -0.12234(9) 0.0416(2) Uani 1 1 d . . .
C19 C 0.3566(2) 0.01299(6) -0.20325(14) 0.0478(4) Uani 1 1 d . . .
H19X H 0.3903 0.0371 -0.2794 0.072 Uiso 1 1 calc R . .
H19Y H 0.2663 -0.0213 -0.2430 0.072 Uiso 1 1 calc R . .
H19Z H 0.4685 -0.0070 -0.1430 0.072 Uiso 1 1 calc R . .
O20 O 0.12880(10) 0.13447(4) 0.04375(9) 0.0324(2) Uani 1 1 d . . .
C21 C 0.11549(19) 0.08010(7) 0.13269(16) 0.0507(4) Uani 1 1 d . . .
H21X H 0.1532 0.0399 0.0928 0.076 Uiso 1 1 calc R . .
H21Y H -0.0134 0.0757 0.1398 0.076 Uiso 1 1 calc R . .
H21Z H 0.1976 0.0875 0.2262 0.076 Uiso 1 1 calc R . .
H5 H 0.0815(15) 0.2588(5) 0.0473(13) 0.028(3) Uiso 1 1 d . . .
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 120.92(9) . . ?
O1 C2 O3 110.36(9) . . ?
O1 C2 C8 110.73(9) . . ?
O3 C2 C8 110.92(10) . . ?
O1 C2 C7 105.04(10) . . ?
O3 C2 C7 105.67(9) . . ?
C8 C2 C7 113.86(11) . . ?
C4 O3 C2 121.16(9) . . ?
O9 C4 O3 118.36(11) . . ?
O9 C4 C5 124.70(11) . . ?
O3 C4 C5 116.93(10) . . ?
C4 C5 C6 112.02(10) . . ?
C4 C5 C11 113.45(10) . . ?
C6 C5 C11 111.91(10) . . ?
O10 C6 O1 118.63(10) . . ?
O10 C6 C5 123.98(11) . . ?
O1 C6 C5 117.38(10) . . ?
C12 C11 C5 115.03(10) . . ?
C17 C12 C13 118.29(11) . . ?
C17 C12 C11 120.21(10) . . ?
C13 C12 C11 121.42(11) . . ?
C14 C13 C12 120.91(12) . . ?
C13 C14 C15 120.73(12) . . ?
C14 C15 C16 119.49(12) . . ?
O18 C16 C15 124.71(11) . . ?
O18 C16 C17 115.77(10) . . ?
C15 C16 C17 119.52(11) . . ?
C12 C17 O20 118.71(10) . . ?
C12 C17 C16 121.06(10) . . ?
O20 C17 C16 120.19(10) . . ?
C16 O18 C19 117.16(10) . . ?
C17 O20 C21 113.71(9) . . ?
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 1.3469(14) . ?
O1 C2 1.4422(14) . ?
C2 O3 1.4462(13) . ?
C2 C8 1.5021(17) . ?
C2 C7 1.5091(16) . ?
O3 C4 1.3553(13) . ?
C4 O9 1.2006(13) . ?
C4 C5 1.5068(16) . ?
C5 C6 1.5118(16) . ?
C5 C11 1.5401(16) . ?
C6 O10 1.1999(13) . ?
C11 C12 1.5086(16) . ?
C12 C17 1.3873(15) . ?
C12 C13 1.3934(16) . ?
C13 C14 1.3775(18) . ?
C14 C15 1.3832(18) . ?
C15 C16 1.3878(16) . ?
C16 O18 1.3731(14) . ?
C16 C17 1.4002(16) . ?
C17 O20 1.3893(12) . ?
O18 C19 1.4279(14) . ?
O20 C21 1.4334(14) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9452826
