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#$Date: 2019-11-23 23:01:21 +0200 (Sat, 23 Nov 2019) $
#$Revision: 235484 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/69/4036965.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_4036965
loop_
_publ_author_name
'Reckenthäler, Melissa'
'Neudörfl, Jörg-M'
'Zorlu, Elif'
'Griesbeck, Axel G.'
_publ_section_title
;
 Combined Photoredox and Lewis Acid Catalyzed α-Hydroxyalkylation of
 Cyclic Ethers with Aromatic Ketones.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7211
_journal_page_last               7216
_journal_paper_doi               10.1021/acs.joc.6b01085
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C12 H16 O3'
_chemical_formula_sum            'C12 H16 O3'
_chemical_formula_weight         208.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.1720(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1871(4)
_cell_length_b                   8.1671(3)
_cell_length_c                   11.3491(4)
_cell_measurement_reflns_used    14120
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.739
_cell_measurement_theta_min      6.715
_cell_volume                     1111.86(7)
_computing_cell_refinement       'Bruker APEX 2'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker APEX 2'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXt  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14120
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.739
_diffrn_reflns_theta_min         6.715
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.028(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0575P)²+0.4530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2075
_reflns_number_total             2202
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b01085_si_001.cif
_cod_data_source_block           mr327
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036965
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.813
_shelx_estimated_absorpt_t_max   0.931
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
O1 O 0.30749(7) 0.78363(11) 0.16255(7) 0.0177(2) Uani 1 1 d
O2 O 0.46517(6) 0.86788(9) 0.36964(7) 0.0151(2) Uani 1 1 d
O3 O 0.56725(7) 0.55618(10) 0.39424(7) 0.0183(2) Uani 1 1 d
C1 C 0.28701(9) 0.76196(14) 0.28182(10) 0.0139(3) Uani 1 1 d
C2 C 0.39772(9) 0.72398(13) 0.36712(10) 0.0132(3) Uani 1 1 d
C3 C 0.57206(10) 0.84323(15) 0.44274(11) 0.0180(3) Uani 1 1 d
C4 C 0.63157(10) 0.70312(15) 0.39505(11) 0.0191(3) Uani 1 1 d
C5 C 0.45790(10) 0.57925(14) 0.32387(11) 0.0170(3) Uani 1 1 d
C6 C 0.20866(9) 0.61610(14) 0.28046(10) 0.0155(3) Uani 1 1 d
C7 C 0.17295(10) 0.56740(16) 0.38577(12) 0.0215(3) Uani 1 1 d
C8 C 0.10310(11) 0.43274(18) 0.38571(14) 0.0287(3) Uani 1 1 d
C9 C 0.06739(11) 0.34477(17) 0.28142(15) 0.0316(4) Uani 1 1 d
C10 C 0.10058(11) 0.39466(18) 0.17642(15) 0.0312(4) Uani 1 1 d
C11 C 0.17073(10) 0.52925(16) 0.17576(12) 0.0229(3) Uani 1 1 d
C12 C 0.23356(10) 0.91770(15) 0.32133(11) 0.0190(3) Uani 1 1 d
H1 H 0.4647(11) 0.5958(18) 0.2399(13) 0.015(3) Uiso 1 1 d
H2 H 0.4181(12) 0.4767(19) 0.3318(13) 0.020(4) Uiso 1 1 d
H3 H 0.3858(11) 0.7025(17) 0.4495(12) 0.011(3) Uiso 1 1 d
H4 H 0.2846(13) 1.012(2) 0.3201(14) 0.025(4) Uiso 1 1 d
H5 H 0.2179(13) 0.906(2) 0.4023(14) 0.024(4) Uiso 1 1 d
H6 H 0.6132(13) 0.947(2) 0.4408(14) 0.022(4) Uiso 1 1 d
H7 H 0.5648(12) 0.8203(18) 0.5272(13) 0.018(3) Uiso 1 1 d
H8 H 0.6421(12) 0.7295(18) 0.3134(14) 0.019(3) Uiso 1 1 d
H9 H 0.1649(15) 0.944(2) 0.2658(16) 0.033(4) Uiso 1 1 d
H10 H 0.1936(14) 0.563(2) 0.1010(15) 0.031(4) Uiso 1 1 d
H11 H 0.0783(15) 0.403(2) 0.4607(17) 0.040(5) Uiso 1 1 d
H12 H 0.7032(13) 0.678(2) 0.4464(14) 0.024(4) Uiso 1 1 d
H13 H 0.1968(13) 0.627(2) 0.4598(15) 0.024(4) Uiso 1 1 d
H14 H 0.0192(16) 0.249(3) 0.2820(17) 0.043(5) Uiso 1 1 d
H15 H 0.3509(16) 0.866(3) 0.1607(16) 0.040(5) Uiso 1 1 d
H16 H 0.0747(14) 0.339(2) 0.1007(17) 0.038(5) 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 0.0181 0.0091 '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 0.0492 0.0322 '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
C1 O1 H15 109.3(12)
C3 O2 C2 110.92(8)
C4 O3 C5 110.23(8)
O1 C1 C6 107.50(9)
O1 C1 C12 109.19(9)
C6 C1 C12 110.71(9)
O1 C1 C2 109.79(9)
C6 C1 C2 108.97(9)
C12 C1 C2 110.63(9)
O2 C2 C5 109.71(9)
O2 C2 C1 106.39(9)
C5 C2 C1 111.82(9)
O2 C2 H3 107.9(8)
C5 C2 H3 109.1(8)
C1 C2 H3 111.8(8)
O2 C3 C4 110.23(9)
O2 C3 H6 106.3(9)
C4 C3 H6 111.4(9)
O2 C3 H7 111.0(8)
C4 C3 H7 109.5(9)
H6 C3 H7 108.3(12)
O3 C4 C3 109.95(9)
O3 C4 H8 109.9(9)
C3 C4 H8 108.9(9)
O3 C4 H12 104.9(10)
C3 C4 H12 112.3(9)
H8 C4 H12 110.8(12)
O3 C5 C2 112.04(9)
O3 C5 H1 109.2(8)
C2 C5 H1 109.6(8)
O3 C5 H2 105.2(9)
C2 C5 H2 111.1(9)
H1 C5 H2 109.6(12)
C11 C6 C7 118.55(11)
C11 C6 C1 121.34(10)
C7 C6 C1 120.12(11)
C8 C7 C6 120.45(13)
C8 C7 H13 119.2(9)
C6 C7 H13 120.4(9)
C9 C8 C7 120.65(13)
C9 C8 H11 120.9(11)
C7 C8 H11 118.4(11)
C10 C9 C8 119.09(12)
C10 C9 H14 120.5(11)
C8 C9 H14 120.4(11)
C9 C10 C11 120.61(13)
C9 C10 H16 121.4(11)
C11 C10 H16 117.9(11)
C6 C11 C10 120.62(13)
C6 C11 H10 119.6(10)
C10 C11 H10 119.8(10)
C1 C12 H4 110.0(9)
C1 C12 H5 111.2(9)
H4 C12 H5 108.3(13)
C1 C12 H9 110.7(10)
H4 C12 H9 106.7(14)
H5 C12 H9 109.8(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4300(13)
O1 H15 0.86(2)
O2 C3 1.4297(14)
O2 C2 1.4316(13)
O3 C4 1.4326(14)
O3 C5 1.4399(14)
C1 C6 1.5251(15)
C1 C12 1.5318(15)
C1 C2 1.5468(15)
C2 C5 1.5176(15)
C2 H3 0.987(14)
C3 C4 1.5056(17)
C3 H6 0.985(16)
C3 H7 0.996(15)
C4 H8 0.981(15)
C4 H12 0.982(16)
C5 H1 0.981(15)
C5 H2 0.980(16)
C6 C11 1.3910(17)
C6 C7 1.4000(17)
C7 C8 1.3907(18)
C7 H13 0.971(17)
C8 C9 1.387(2)
C8 H11 0.983(19)
C9 C10 1.386(2)
C9 H14 0.98(2)
C10 C11 1.3934(19)
C10 H16 0.976(19)
C11 H10 0.979(17)
C12 H4 0.993(17)
C12 H5 0.975(16)
C12 H9 0.978(18)
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
C3 O2 C2 C5 -56.50(11)
C3 O2 C2 C1 -177.63(8)
O1 C1 C2 O2 65.54(10)
C6 C1 C2 O2 -176.97(8)
C12 C1 C2 O2 -55.03(11)
O1 C1 C2 C5 -54.23(12)
C6 C1 C2 C5 63.26(12)
C12 C1 C2 C5 -174.80(9)
C2 O2 C3 C4 59.62(12)
C5 O3 C4 C3 57.39(12)
O2 C3 C4 O3 -59.68(12)
C4 O3 C5 C2 -55.78(12)
O2 C2 C5 O3 54.87(12)
C1 C2 C5 O3 172.66(9)
O1 C1 C6 C11 0.46(15)
C12 C1 C6 C11 119.65(12)
C2 C1 C6 C11 -118.46(12)
O1 C1 C6 C7 -179.24(10)
C12 C1 C6 C7 -60.05(14)
C2 C1 C6 C7 61.84(13)
C11 C6 C7 C8 1.44(18)
C1 C6 C7 C8 -178.85(11)
C6 C7 C8 C9 -0.2(2)
C7 C8 C9 C10 -1.2(2)
C8 C9 C10 C11 1.3(2)
C7 C6 C11 C10 -1.32(19)
C1 C6 C11 C10 178.98(11)
C9 C10 C11 C6 -0.1(2)
