#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/62/1516235.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_1516235
loop_
_publ_author_name
'Rout, Saroj Kumar'
'Guin, Srimanta'
'Ali, Wajid'
'Gogoi, Anupal'
'Patel, Bhisma K.'
_publ_section_title
;
 Copper-Catalyzed Esterification of Alkylbenzenes with Cyclic Ethers and
 Cycloalkanes via C(sp(3))-H Activation Following Cross-Dehydrogenative
 Coupling.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              3086
_journal_page_last               3089
_journal_paper_doi               10.1021/ol5011906
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C13 H16 O6'
_chemical_formula_sum            'C13 H16 O6'
_chemical_formula_weight         268.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   11.5879(2)
_cell_length_b                   11.6170(2)
_cell_length_c                   19.7761(4)
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.82
_cell_measurement_theta_min      2.69
_cell_volume                     2662.19(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0652
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28687
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          .22
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0710P)²+0.0030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                1594
_reflns_number_total             2340
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5011906_si_002.cif
_cod_data_source_block           skr-203_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1516235.cif.
;
_cod_database_code               1516235
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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
O4 O 0.99158(8) 0.66269(8) 0.42239(5) 0.0473(3) Uani 1 1 d .
O6 O 1.18637(10) 0.70192(10) 0.43828(5) 0.0603(3) Uani 1 1 d .
O1 O 1.02264(11) 0.70137(10) 0.27773(6) 0.0715(4) Uani 1 1 d .
C9 C 0.98401(12) 0.56417(12) 0.38670(7) 0.0396(3) Uani 1 1 d .
C6 C 0.89915(12) 0.57146(12) 0.33022(7) 0.0433(4) Uani 1 1 d .
O5 O 1.04595(12) 0.86949(10) 0.50047(6) 0.0739(4) Uani 1 1 d .
C10 C 1.08537(13) 0.67011(13) 0.47143(7) 0.0492(4) Uani 1 1 d .
H10 H 1.0965 0.5946 0.4925 0.059 Uiso 1 1 calc R
C5 C 0.79919(13) 0.50498(13) 0.33116(8) 0.0530(4) Uani 1 1 d .
C1 C 0.92570(14) 0.63630(14) 0.27274(8) 0.0545(4) Uani 1 1 d .
C11 C 1.04885(17) 0.75494(15) 0.52447(8) 0.0645(5) Uani 1 1 d .
H11A H 0.9727 0.7341 0.5408 0.077 Uiso 1 1 calc R
H11B H 1.1019 0.7504 0.5623 0.077 Uiso 1 1 calc R
C4 C 0.72825(16) 0.50123(18) 0.27469(11) 0.0769(6) Uani 1 1 d .
H4 H 0.6608 0.4579 0.2751 0.092 Uiso 1 1 calc R
C13 C 1.18335(17) 0.81989(15) 0.41495(10) 0.0714(5) Uani 1 1 d .
H13A H 1.1260 0.8275 0.3795 0.086 Uiso 1 1 calc R
H13B H 1.2579 0.8404 0.3961 0.086 Uiso 1 1 calc R
C2 C 0.85590(19) 0.63061(18) 0.21594(9) 0.0772(6) Uani 1 1 d .
H2 H 0.8742 0.6720 0.1772 0.093 Uiso 1 1 calc R
C12 C 1.15465(19) 0.89981(16) 0.47158(11) 0.0818(6) Uani 1 1 d .
H12A H 1.2143 0.8957 0.5059 0.098 Uiso 1 1 calc R
H12B H 1.1516 0.9782 0.4548 0.098 Uiso 1 1 calc R
C3 C 0.7592(2) 0.5625(2) 0.21816(11) 0.0881(7) Uani 1 1 d .
H3 H 0.7128 0.5577 0.1799 0.106 Uiso 1 1 calc R
O2 O 0.78018(9) 0.44643(9) 0.38997(6) 0.0649(4) Uani 1 1 d .
C8 C 0.67434(17) 0.38380(18) 0.39709(13) 0.0941(7) Uani 1 1 d .
H8A H 0.6103 0.4354 0.3917 0.141 Uiso 1 1 calc R
H8B H 0.6713 0.3492 0.4411 0.141 Uiso 1 1 calc R
H8C H 0.6705 0.3248 0.3632 0.141 Uiso 1 1 calc R
C7 C 1.0618(2) 0.7623(2) 0.21907(11) 0.1059(8) Uani 1 1 d .
H7A H 1.0767 0.7085 0.1833 0.159 Uiso 1 1 calc R
H7B H 1.1314 0.8033 0.2297 0.159 Uiso 1 1 calc R
H7C H 1.0035 0.8158 0.2049 0.159 Uiso 1 1 calc R
O3 O 1.04069(10) 0.47999(9) 0.39863(5) 0.0549(3) Uani 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
C9 O4 C10 116.54(11)
C10 O6 C13 112.43(12)
C1 O1 C7 118.56(15)
O3 C9 O4 123.57(13)
O3 C9 C6 123.64(12)
O4 C9 C6 112.78(12)
C5 C6 C1 119.52(14)
C5 C6 C9 120.49(13)
C1 C6 C9 119.65(13)
C11 O5 C12 110.23(14)
O6 C10 O4 109.21(11)
O6 C10 C11 113.09(13)
O4 C10 C11 107.06(13)
O2 C5 C4 125.07(16)
O2 C5 C6 114.95(13)
C4 C5 C6 119.98(16)
O1 C1 C2 124.65(16)
O1 C1 C6 115.03(13)
C2 C1 C6 120.33(17)
O5 C11 C10 112.99(14)
C3 C4 C5 118.98(19)
O6 C13 C12 110.82(15)
C3 C2 C1 118.58(19)
O5 C12 C13 110.10(15)
C4 C3 C2 122.55(18)
C5 O2 C8 118.33(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C9 1.3475(16)
O4 C10 1.4591(17)
O6 C10 1.3914(18)
O6 C13 1.4464(19)
O1 C1 1.3576(19)
O1 C7 1.432(2)
C9 O3 1.2014(16)
C9 C6 1.4905(19)
C6 C5 1.392(2)
C6 C1 1.398(2)
O5 C11 1.413(2)
O5 C12 1.427(2)
C10 C11 1.500(2)
C5 O2 1.3653(18)
C5 C4 1.387(2)
C1 C2 1.386(2)
C4 C3 1.373(3)
C13 C12 1.492(3)
C2 C3 1.372(3)
O2 C8 1.433(2)
