#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/22/1512286.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_1512286
loop_
_publ_author_name
'Baran, Arif'
'Aydin, Gokay'
'Savran, Tahir'
'Sahin, Ertan'
'Balci, Metin'
_publ_section_title
;
 Trisequential photooxygenation reaction: application to the synthesis of
 carbasugars.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4350
_journal_page_last               4353
_journal_paper_doi               10.1021/ol401823m
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C8 H10 O6'
_chemical_formula_sum            'C8 H10 O6'
_chemical_formula_weight         202.16
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_date             2013-08-02T12:33:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 92.995(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0191(5)
_cell_length_b                   10.9331(7)
_cell_length_c                   13.1204(8)
_cell_measurement_temperature    293(2)
_cell_volume                     862.24(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device
;
RAXIS conversion
;
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_detector       RX
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16087
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.052
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0510P)²+0.5409P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.131
_reflns_number_gt                1515
_reflns_number_total             1520
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol401823m_si_002.cif
_cod_data_source_block           f2plus
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1512286
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
O5 O 2.2108(3) -0.02647(14) 0.67128(12) 0.0455(4) Uani 1 1 d .
O3 O 1.6257(2) 0.15512(15) 0.72023(12) 0.0433(4) Uani 1 1 d .
O4 O 1.7657(3) 0.20135(16) 0.63838(11) 0.0494(5) Uani 1 1 d .
O6 O 2.3394(3) 0.00905(19) 0.58438(13) 0.0570(5) Uani 1 1 d .
H6 H 2.4421 0.0538 0.6041 0.086 Uiso 1 1 calc R
C5 C 1.9939(3) 0.02355(19) 0.65410(15) 0.0361(5) Uani 1 1 d .
H5 H 1.9283 -0.0039 0.5881 0.043 Uiso 1 1 calc R
O1 O 1.8140(4) 0.1313(2) 1.00384(14) 0.0859(7) Uani 1 1 d .
C4 C 1.9946(4) 0.16316(19) 0.65941(16) 0.0393(5) Uani 1 1 d .
H4 H 2.0896 0.1968 0.6078 0.047 Uiso 1 1 calc R
C7 C 1.7615(3) 0.08497(19) 0.79558(15) 0.0350(5) Uani 1 1 d .
C2 C 1.9456(4) 0.16789(19) 0.83509(16) 0.0378(5) Uani 1 1 d .
O2 O 1.5913(4) 0.1368(2) 0.95266(16) 0.0800(7) Uani 1 1 d .
C6 C 1.8580(4) -0.02438(19) 0.74085(16) 0.0385(5) Uani 1 1 d .
H6A H 1.7389 -0.0767 0.7137 0.046 Uiso 1 1 calc R
H6B H 1.9522 -0.0719 0.7882 0.046 Uiso 1 1 calc R
C8 C 1.5988(4) 0.0485(3) 0.87456(19) 0.0539(6) Uani 1 1 d .
H8A H 1.4516 0.0391 0.8417 0.065 Uiso 1 1 calc R
H8B H 1.6429 -0.0297 0.9041 0.065 Uiso 1 1 calc R
C3 C 2.0706(4) 0.20708(19) 0.76216(18) 0.0428(5) Uani 1 1 d .
H3 H 2.1941 0.2572 0.7741 0.051 Uiso 1 1 calc R
C1 C 1.9579(6) 0.2046(3) 0.94526(19) 0.0670(8) Uani 1 1 d .
H1A H 2.1098 0.1959 0.9728 0.08 Uiso 1 1 calc R
H1B H 1.9161 0.2899 0.9509 0.08 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C5 O5 O6 107.03(15)
C7 O3 O4 110.35(13)
C4 O4 O3 109.42(13)
O5 O6 H6 109.5
O5 C5 C4 112.11(18)
O5 C5 C6 105.82(16)
C4 C5 C6 107.98(17)
O5 C5 H5 110.3
C4 C5 H5 110.3
C6 C5 H5 110.3
C1 O1 O2 107.1(2)
O4 C4 C3 108.95(17)
O4 C4 C5 106.15(18)
C3 C4 C5 111.44(18)
O4 C4 H4 110.1
C3 C4 H4 110.1
C5 C4 H4 110.1
O3 C7 C2 106.98(16)
O3 C7 C8 103.96(17)
C2 C7 C8 114.47(18)
O3 C7 C6 107.77(16)
C2 C7 C6 110.09(17)
C8 C7 C6 113.00(18)
C3 C2 C1 127.7(2)
C3 C2 C7 112.58(19)
C1 C2 C7 119.5(2)
C8 O2 O1 104.0(2)
C7 C6 C5 108.28(16)
C7 C6 H6A 110
C5 C6 H6A 110
C7 C6 H6B 110
C5 C6 H6B 110
H6A C6 H6B 108.4
O2 C8 C7 111.2(2)
O2 C8 H8A 109.4
C7 C8 H8A 109.4
O2 C8 H8B 109.4
C7 C8 H8B 109.4
H8A C8 H8B 108
C2 C3 C4 113.21(19)
C2 C3 H3 123.4
C4 C3 H3 123.4
O1 C1 C2 111.5(2)
O1 C1 H1A 109.3
C2 C1 H1A 109.3
O1 C1 H1B 109.3
C2 C1 H1B 109.3
H1A C1 H1B 108
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O5 C5 1.423(3)
O5 O6 1.464(2)
O3 C7 1.466(2)
O3 O4 1.488(2)
O4 C4 1.452(3)
O6 H6 0.82
C5 C4 1.528(3)
C5 C6 1.529(3)
C5 H5 0.98
O1 C1 1.432(4)
O1 O2 1.469(3)
C4 C3 1.481(3)
C4 H4 0.98
C7 C2 1.503(3)
C7 C8 1.516(3)
C7 C6 1.525(3)
C2 C3 1.319(3)
C2 C1 1.498(3)
O2 C8 1.411(3)
C6 H6A 0.97
C6 H6B 0.97
C8 H8A 0.97
C8 H8B 0.97
C3 H3 0.93
C1 H1A 0.97
C1 H1B 0.97
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C7 O3 O4 C4 -0.5(2)
O6 O5 C5 C4 -67.4(2)
O6 O5 C5 C6 175.09(15)
O3 O4 C4 C3 -56.3(2)
O3 O4 C4 C5 63.8(2)
O5 C5 C4 O4 178.74(15)
C6 C5 C4 O4 -65.1(2)
O5 C5 C4 C3 -62.8(2)
C6 C5 C4 C3 53.4(2)
O4 O3 C7 C2 56.7(2)
O4 O3 C7 C8 178.15(17)
O4 O3 C7 C6 -61.69(19)
O3 C7 C2 C3 -59.2(2)
C8 C7 C2 C3 -173.8(2)
C6 C7 C2 C3 57.6(2)
O3 C7 C2 C1 116.0(2)
C8 C7 C2 C1 1.4(3)
C6 C7 C2 C1 -127.2(2)
C1 O1 O2 C8 82.5(3)
O3 C7 C6 C5 58.2(2)
C2 C7 C6 C5 -58.1(2)
C8 C7 C6 C5 172.52(18)
O5 C5 C6 C7 123.93(18)
C4 C5 C6 C7 3.7(2)
O1 O2 C8 C7 -65.8(3)
O3 C7 C8 O2 -90.4(2)
C2 C7 C8 O2 25.9(3)
C6 C7 C8 O2 153.0(2)
C1 C2 C3 C4 -172.8(2)
C7 C2 C3 C4 1.9(3)
O4 C4 C3 C2 57.4(2)
C5 C4 C3 C2 -59.4(2)
O2 O1 C1 C2 -52.9(3)
C3 C2 C1 O1 -172.7(2)
C7 C2 C1 O1 13.0(3)
