#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/42/4024299.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_4024299
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 H17 F O4'
_chemical_formula_weight         280.29
_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                 98.917(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8109(17)
_cell_length_b                   20.468(5)
_cell_length_c                   10.125(3)
_cell_measurement_temperature    180(2)
_cell_volume                     1394.4(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12854
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.9743
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'APEX II'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0054(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   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         4064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0412
_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)+(0.0249P)²+0.2943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                3170
_reflns_number_total             4064
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802311w_si_008.cif
_cod_data_source_block           aw-2-221_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
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               4024299
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 0.82896(13) 0.55722(4) 0.60227(8) 0.0367(2) Uani 1 1 d . . .
C2 C 0.8388(2) 0.62431(6) 0.64449(12) 0.0380(3) Uani 1 1 d . . .
O3 O 0.88894(13) 0.66516(4) 0.53893(8) 0.0370(2) Uani 1 1 d . . .
C4 C 0.80092(16) 0.65615(6) 0.41170(11) 0.0285(2) Uani 1 1 d . . .
C5 C 0.66854(16) 0.59597(5) 0.38458(11) 0.0273(2) Uani 1 1 d . . .
H5 H 0.5389 0.6087 0.4120 0.033 Uiso 1 1 calc R . .
C6 C 0.74640(17) 0.54001(6) 0.47710(12) 0.0325(3) Uani 1 1 d . . .
C7 C 1.0141(3) 0.62840(8) 0.75533(15) 0.0598(4) Uani 1 1 d . . .
H7X H 1.1339 0.6130 0.7224 0.090 Uiso 1 1 calc R . .
H7Y H 0.9892 0.6010 0.8304 0.090 Uiso 1 1 calc R . .
H7Z H 1.0330 0.6738 0.7852 0.090 Uiso 1 1 calc R . .
C8 C 0.6464(2) 0.64661(7) 0.68610(14) 0.0470(3) Uani 1 1 d . . .
H8X H 0.5388 0.6428 0.6101 0.071 Uiso 1 1 calc R . .
H8Y H 0.6591 0.6922 0.7154 0.071 Uiso 1 1 calc R . .
H8Z H 0.6162 0.6192 0.7598 0.071 Uiso 1 1 calc R . .
O9 O 0.83232(12) 0.69504(4) 0.32942(8) 0.0352(2) Uani 1 1 d . . .
O10 O 0.73644(16) 0.48310(4) 0.45021(10) 0.0470(2) Uani 1 1 d . . .
C11 C 0.61853(16) 0.57958(6) 0.23254(11) 0.0292(2) Uani 1 1 d . . .
C12 C 0.50722(16) 0.63719(6) 0.15839(11) 0.0282(2) Uani 1 1 d . . .
C13 C 0.56670(18) 0.66725(6) 0.04738(12) 0.0337(3) Uani 1 1 d . . .
H13 H 0.6883 0.6543 0.0203 0.040 Uiso 1 1 calc R . .
C14 C 0.45385(19) 0.71550(7) -0.02470(12) 0.0382(3) Uani 1 1 d . . .
H14 H 0.4988 0.7346 -0.1002 0.046 Uiso 1 1 calc R . .
C15 C 0.27654(19) 0.73615(7) 0.01214(13) 0.0389(3) Uani 1 1 d . . .
H15 H 0.1995 0.7691 -0.0376 0.047 Uiso 1 1 calc R . .
C16 C 0.21319(18) 0.70821(7) 0.12208(13) 0.0369(3) Uani 1 1 d . . .
H16 H 0.0926 0.7218 0.1498 0.044 Uiso 1 1 calc R . .
C17 C 0.32782(17) 0.66026(6) 0.19075(11) 0.0318(3) Uani 1 1 d . . .
F18 F 0.25830(10) 0.63402(4) 0.29890(7) 0.0434(2) Uani 1 1 d . . .
C19 C 0.81115(18) 0.56261(7) 0.17894(13) 0.0370(3) Uani 1 1 d . . .
H19X H 0.7803 0.5522 0.0835 0.056 Uiso 1 1 calc R . .
H19Y H 0.8741 0.5247 0.2274 0.056 Uiso 1 1 calc R . .
H19Z H 0.9020 0.6000 0.1917 0.056 Uiso 1 1 calc R . .
C20 C 0.4774(2) 0.52006(6) 0.20766(14) 0.0403(3) Uani 1 1 d . . .
H20X H 0.4490 0.5109 0.1116 0.060 Uiso 1 1 calc R . .
H20Y H 0.3530 0.5297 0.2411 0.060 Uiso 1 1 calc R . .
H20Z H 0.5408 0.4818 0.2546 0.060 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'
F F 0.0171 0.0103 '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 121.44(9) . . ?
O1 C2 O3 109.87(10) . . ?
O1 C2 C8 111.71(11) . . ?
O3 C2 C8 110.37(11) . . ?
O1 C2 C7 105.63(11) . . ?
O3 C2 C7 105.58(11) . . ?
C8 C2 C7 113.40(12) . . ?
C4 O3 C2 120.61(9) . . ?
O9 C4 O3 118.32(10) . . ?
O9 C4 C5 125.22(10) . . ?
O3 C4 C5 116.47(10) . . ?
C6 C5 C4 110.91(9) . . ?
C6 C5 C11 116.57(9) . . ?
C4 C5 C11 112.55(9) . . ?
O10 C6 O1 117.91(11) . . ?
O10 C6 C5 126.22(11) . . ?
O1 C6 C5 115.84(10) . . ?
C12 C11 C19 112.67(10) . . ?
C12 C11 C20 106.14(9) . . ?
C19 C11 C20 107.91(10) . . ?
C12 C11 C5 109.47(9) . . ?
C19 C11 C5 109.24(9) . . ?
C20 C11 C5 111.39(9) . . ?
C13 C12 C17 114.45(11) . . ?
C13 C12 C11 123.37(10) . . ?
C17 C12 C11 121.98(10) . . ?
C14 C13 C12 122.09(11) . . ?
C15 C14 C13 120.72(12) . . ?
C16 C15 C14 119.09(12) . . ?
C17 C16 C15 118.71(12) . . ?
F18 C17 C16 116.44(10) . . ?
F18 C17 C12 118.63(11) . . ?
C16 C17 C12 124.93(11) . . ?
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 1.3511(15) . ?
O1 C2 1.4366(15) . ?
C2 O3 1.4392(15) . ?
C2 C8 1.508(2) . ?
C2 C7 1.509(2) . ?
O3 C4 1.3465(14) . ?
C4 O9 1.1953(14) . ?
C4 C5 1.5261(16) . ?
C5 C6 1.5220(17) . ?
C5 C11 1.5606(16) . ?
C6 O10 1.1958(15) . ?
C11 C12 1.5337(17) . ?
C11 C19 1.5353(16) . ?
C11 C20 1.5482(16) . ?
C12 C13 1.3953(16) . ?
C12 C17 1.3955(16) . ?
C13 C14 1.3874(18) . ?
C14 C15 1.3842(18) . ?
C15 C16 1.3788(18) . ?
C16 C17 1.3740(18) . ?
C17 F18 1.3684(13) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658883
