#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/42/4024296.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_4024296
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            'C17 H22 O6'
_chemical_formula_weight         322.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                   22.5294(12)
_cell_length_b                   13.8214(8)
_cell_length_c                   10.7410(6)
_cell_measurement_reflns_used    5285
_cell_measurement_temperature    297(1)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      2.57
_cell_volume                     3344.6(3)
_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      297(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  0.0591
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22868
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Needle prism fragment'
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0041(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.992
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0280P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                2761
_reflns_number_total             3421
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802311w_si_005.cif
_cod_data_source_block           ef1267rm
_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      Pbcn
_cod_database_code               4024296
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, 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 0.09339(6) 0.05569(9) 0.80231(11) 0.0626(4) Uani 1 1 d . . .
C2 C 0.10914(9) -0.00314(14) 0.69809(17) 0.0617(5) Uani 1 1 d . . .
O3 O 0.16174(6) 0.03427(9) 0.64161(12) 0.0640(4) Uani 1 1 d . . .
C4 C 0.16891(8) 0.13023(13) 0.62419(16) 0.0504(4) Uani 1 1 d . . .
C5 C 0.12171(8) 0.19575(13) 0.67874(16) 0.0489(4) Uani 1 1 d . . .
C6 C 0.09558(9) 0.15269(14) 0.79580(18) 0.0620(5) Uani 1 1 d . . .
C7 C 0.12577(12) -0.10012(15) 0.7506(3) 0.0993(8) Uani 1 1 d . . .
H7X H 0.1578 -0.0925 0.8088 0.149 Uiso 1 1 calc R . .
H7Y H 0.1381 -0.1421 0.6843 0.149 Uiso 1 1 calc R . .
H7Z H 0.0921 -0.1278 0.7923 0.149 Uiso 1 1 calc R . .
C8 C 0.05900(10) -0.00664(19) 0.60613(19) 0.0851(7) Uani 1 1 d . . .
H8X H 0.0698 -0.0475 0.5375 0.128 Uiso 1 1 calc R . .
H8Y H 0.0509 0.0575 0.5762 0.128 Uiso 1 1 calc R . .
H8Z H 0.0242 -0.0321 0.6459 0.128 Uiso 1 1 calc R . .
O9 O 0.21129(6) 0.15595(9) 0.56781(13) 0.0680(4) Uani 1 1 d . . .
O10 O 0.07661(9) 0.19629(11) 0.88290(15) 0.1033(6) Uani 1 1 d . . .
C11 C 0.14184(8) 0.30364(13) 0.68949(16) 0.0512(4) Uani 1 1 d . . .
C12 C 0.16307(7) 0.34080(12) 0.56187(15) 0.0462(4) Uani 1 1 d . . .
C13 C 0.21732(8) 0.38876(13) 0.54961(17) 0.0559(5) Uani 1 1 d . . .
H13 H 0.2411 0.3971 0.6196 0.067 Uiso 1 1 calc R . .
C14 C 0.23646(8) 0.42390(14) 0.43720(17) 0.0597(5) Uani 1 1 d . . .
H14 H 0.2723 0.4570 0.4329 0.072 Uiso 1 1 calc R . .
C15 C 0.20360(8) 0.41102(13) 0.33115(17) 0.0544(5) Uani 1 1 d . . .
H15 H 0.2175 0.4336 0.2550 0.065 Uiso 1 1 calc R . .
C16 C 0.14960(7) 0.36420(13) 0.33856(16) 0.0490(4) Uani 1 1 d . . .
C17 C 0.12889(7) 0.33230(12) 0.45433(15) 0.0477(4) Uani 1 1 d . . .
O18 O 0.11397(5) 0.34531(10) 0.23873(11) 0.0629(4) Uani 1 1 d . . .
C19 C 0.13862(9) 0.35837(16) 0.11780(17) 0.0703(6) Uani 1 1 d . . .
H19X H 0.1757 0.3244 0.1123 0.105 Uiso 1 1 calc R . .
H19Y H 0.1451 0.4261 0.1031 0.105 Uiso 1 1 calc R . .
H19Z H 0.1116 0.3335 0.0565 0.105 Uiso 1 1 calc R . .
O20 O 0.07495(5) 0.28420(11) 0.45998(11) 0.0653(4) Uani 1 1 d . . .
C21 C 0.02372(9) 0.3405(2) 0.4286(2) 0.1042(10) Uani 1 1 d . . .
H21X H 0.0237 0.3534 0.3408 0.156 Uiso 1 1 calc R . .
H21Y H 0.0247 0.4005 0.4736 0.156 Uiso 1 1 calc R . .
H21Z H -0.0115 0.3053 0.4505 0.156 Uiso 1 1 calc R . .
C22 C 0.19078(9) 0.30949(15) 0.78849(17) 0.0670(5) Uani 1 1 d . . .
H22X H 0.2004 0.3761 0.8039 0.100 Uiso 1 1 calc R . .
H22Y H 0.2254 0.2760 0.7593 0.100 Uiso 1 1 calc R . .
H22Z H 0.1771 0.2800 0.8641 0.100 Uiso 1 1 calc R . .
C23 C 0.08945(9) 0.36859(14) 0.73044(19) 0.0675(6) Uani 1 1 d . . .
H23X H 0.0554 0.3550 0.6795 0.101 Uiso 1 1 calc R . .
H23Y H 0.1003 0.4354 0.7212 0.101 Uiso 1 1 calc R . .
H23Z H 0.0800 0.3557 0.8160 0.101 Uiso 1 1 calc R . .
H5 H 0.0906(7) 0.1950(10) 0.6205(15) 0.037(4) 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 121.21(14) . . ?
O3 C2 O1 109.44(14) . . ?
O3 C2 C8 110.89(16) . . ?
O1 C2 C8 110.30(16) . . ?
O3 C2 C7 106.00(16) . . ?
O1 C2 C7 106.01(17) . . ?
C8 C2 C7 113.96(19) . . ?
C4 O3 C2 120.94(14) . . ?
O9 C4 O3 117.53(15) . . ?
O9 C4 C5 125.72(17) . . ?
O3 C4 C5 116.75(15) . . ?
C6 C5 C4 111.10(15) . . ?
C6 C5 C11 115.30(14) . . ?
C4 C5 C11 113.29(14) . . ?
O10 C6 O1 116.77(17) . . ?
O10 C6 C5 126.43(18) . . ?
O1 C6 C5 116.80(15) . . ?
C22 C11 C12 112.10(15) . . ?
C22 C11 C23 108.71(15) . . ?
C12 C11 C23 107.25(14) . . ?
C22 C11 C5 108.06(15) . . ?
C12 C11 C5 110.03(13) . . ?
C23 C11 C5 110.70(14) . . ?
C17 C12 C13 116.46(15) . . ?
C17 C12 C11 122.56(15) . . ?
C13 C12 C11 120.94(15) . . ?
C14 C13 C12 121.76(17) . . ?
C15 C14 C13 121.08(17) . . ?
C14 C15 C16 119.29(16) . . ?
O18 C16 C15 124.25(15) . . ?
O18 C16 C17 116.21(15) . . ?
C15 C16 C17 119.53(16) . . ?
O20 C17 C12 119.25(14) . . ?
O20 C17 C16 118.83(14) . . ?
C12 C17 C16 121.72(15) . . ?
C16 O18 C19 117.58(14) . . ?
C17 O20 C21 115.83(17) . . ?
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 1.343(2) . ?
O1 C2 1.428(2) . ?
C2 O3 1.428(2) . ?
C2 C8 1.501(3) . ?
C2 C7 1.502(3) . ?
O3 C4 1.349(2) . ?
C4 O9 1.185(2) . ?
C4 C5 1.515(2) . ?
C5 C6 1.510(2) . ?
C5 C11 1.563(3) . ?
C6 O10 1.192(2) . ?
C11 C22 1.534(3) . ?
C11 C12 1.540(2) . ?
C11 C23 1.547(2) . ?
C12 C17 1.393(2) . ?
C12 C13 1.397(2) . ?
C13 C14 1.371(3) . ?
C14 C15 1.370(3) . ?
C15 C16 1.380(2) . ?
C16 O18 1.365(2) . ?
C16 C17 1.399(2) . ?
C17 O20 1.3865(19) . ?
O18 C19 1.424(2) . ?
O20 C21 1.432(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9613509
