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#$Date: 2022-05-12 01:12:03 +0300 (Thu, 12 May 2022) $
#$Revision: 275346 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/69/1566956.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_1566956
loop_
_publ_author_name
'Sandvoß, Alexander'
'Maag, Henning'
'Daniliuc, Constantin G.'
'Schollmeyer, Dieter'
'Wahl, Johannes M.'
_publ_section_title
;
 Dynamic kinetic resolution of transient hemiketals: a strategy for the
 desymmetrisation of prochiral oxetanols
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC01547A
_journal_year                    2022
_chemical_formula_sum            'C15 H12 F3 N O4'
_chemical_formula_weight         327.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           'APEX3 v2016.1-0'
_audit_update_record
;
2021-12-21 deposited with the CCDC.	2022-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.5889(3)
_cell_length_b                   9.9317(2)
_cell_length_c                   20.9678(4)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      68.3384
_cell_measurement_theta_min      4.2170
_cell_volume                     2829.83(10)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22240
_diffrn_reflns_theta_full        68.36
_diffrn_reflns_theta_max         68.36
_diffrn_reflns_theta_min         4.22
_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    1.198
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.272
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0317P)²+1.4456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0827
_reflns_number_gt                2349
_reflns_number_total             2578
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc01547a2.cif
_cod_data_source_block           wie9750
_cod_database_code               1566956
loop_
_space_group_symop_operation_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.57497(10) 0.64451(13) 0.64723(6) 0.0166(3) Uani d . . . 1 . .
O O1 0.57958(7) 0.68339(9) 0.71167(4) 0.0166(2) Uani d . . . 1 . .
O O2 0.63916(7) 0.71685(11) 0.60836(5) 0.0208(2) Uani d . . . 1 . .
H H2 0.6326(14) 0.797(2) 0.6162(9) 0.032(5) Uiso d . . . 1 . .
C C2 0.46821(11) 0.67967(14) 0.62852(7) 0.0212(3) Uani d . . . 1 . .
F F1 0.40243(6) 0.62316(9) 0.66759(4) 0.0261(2) Uani d . . . 1 . .
F F2 0.45363(7) 0.81270(9) 0.63010(5) 0.0312(2) Uani d . . . 1 . .
F F3 0.44795(7) 0.63852(9) 0.56923(4) 0.0293(2) Uani d . . . 1 . .
C C3 0.67807(10) 0.68572(14) 0.73815(7) 0.0189(3) Uani d . . . 1 . .
H H3A 0.7161 0.7615 0.7199 0.023 Uiso calc U . R 1 . .
H H3B 0.7128 0.6007 0.7282 0.023 Uiso calc U . R 1 . .
C C11 0.66816(9) 0.70232(14) 0.80896(7) 0.0171(3) Uani d . . . 1 . .
C C12 0.68879(10) 0.82477(14) 0.83785(7) 0.0218(3) Uani d . . . 1 . .
H H12 0.7103 0.8986 0.8127 0.026 Uiso calc U . R 1 . .
C C13 0.67813(11) 0.84015(15) 0.90339(8) 0.0263(3) Uani d . . . 1 . .
H H13 0.6928 0.9242 0.9228 0.032 Uiso calc U . R 1 . .
C C14 0.64618(11) 0.73321(16) 0.94041(7) 0.0255(3) Uani d . . . 1 . .
H H14 0.6386 0.7438 0.9852 0.031 Uiso calc U . R 1 . .
C C15 0.62528(11) 0.61027(15) 0.91174(7) 0.0241(3) Uani d . . . 1 . .
H H15 0.6033 0.5366 0.9369 0.029 Uiso calc U . R 1 . .
C C16 0.63647(10) 0.59522(14) 0.84656(7) 0.0202(3) Uani d . . . 1 . .
H H16 0.6224 0.5109 0.8272 0.024 Uiso calc U . R 1 . .
C C21 0.59309(9) 0.49448(13) 0.63707(6) 0.0155(3) Uani d . . . 1 . .
C C22 0.56702(9) 0.40314(14) 0.68465(6) 0.0167(3) Uani d . . . 1 . .
H H22 0.5398 0.4349 0.7236 0.02 Uiso calc U . R 1 . .
C C23 0.58061(10) 0.26624(14) 0.67541(7) 0.0172(3) Uani d . . . 1 . .
H H23 0.5647 0.2034 0.708 0.021 Uiso calc U . R 1 . .
C C24 0.61794(10) 0.22361(13) 0.61743(7) 0.0171(3) Uani d . . . 1 . .
C C25 0.64305(10) 0.31139(14) 0.56880(7) 0.0189(3) Uani d . . . 1 . .
H H25 0.668 0.2788 0.5294 0.023 Uiso calc U . R 1 . .
C C26 0.63080(10) 0.44805(14) 0.57922(7) 0.0186(3) Uani d . . . 1 . .
H H26 0.6482 0.5105 0.5468 0.022 Uiso calc U . R 1 . .
N N1 0.63076(9) 0.07872(12) 0.60657(6) 0.0212(3) Uani d . . . 1 . .
O O3 0.62895(8) 0.00250(10) 0.65297(5) 0.0275(3) Uani d . . . 1 . .
O O4 0.64296(8) 0.03868(11) 0.55170(5) 0.0308(3) Uani d . . . 1 . .
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'
N N 0.0311 0.0180 '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'
F F 0.0727 0.0534 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 C1 O1 . . 113.10(11) ?
O2 C1 C21 . . 108.73(11) ?
O1 C1 C21 . . 113.27(11) ?
O2 C1 C2 . . 108.86(11) ?
O1 C1 C2 . . 102.95(10) ?
C21 C1 C2 . . 109.72(11) ?
C1 O1 C3 . . 114.43(10) ?
C1 O2 H2 . . 108.5(14) ?
F1 C2 F2 . . 107.51(11) ?
F1 C2 F3 . . 107.69(11) ?
F2 C2 F3 . . 107.14(12) ?
F1 C2 C1 . . 112.22(11) ?
F2 C2 C1 . . 110.90(12) ?
F3 C2 C1 . . 111.15(11) ?
O1 C3 C11 . . 107.35(10) ?
O1 C3 H3A . . 110.2 ?
C11 C3 H3A . . 110.2 ?
O1 C3 H3B . . 110.2 ?
C11 C3 H3B . . 110.2 ?
H3A C3 H3B . . 108.5 ?
C12 C11 C16 . . 119.01(13) ?
C12 C11 C3 . . 120.69(13) ?
C16 C11 C3 . . 120.29(12) ?
C11 C12 C13 . . 120.46(14) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C14 C13 C12 . . 120.15(14) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 119.67(14) ?
C13 C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
C16 C15 C14 . . 119.98(14) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
C15 C16 C11 . . 120.73(13) ?
C15 C16 H16 . . 119.6 ?
C11 C16 H16 . . 119.6 ?
C22 C21 C26 . . 120.03(12) ?
C22 C21 C1 . . 119.66(12) ?
C26 C21 C1 . . 120.23(12) ?
C23 C22 C21 . . 120.30(13) ?
C23 C22 H22 . . 119.8 ?
C21 C22 H22 . . 119.8 ?
C24 C23 C22 . . 118.16(13) ?
C24 C23 H23 . . 120.9 ?
C22 C23 H23 . . 120.9 ?
C23 C24 C25 . . 123.01(13) ?
C23 C24 N1 . . 118.68(12) ?
C25 C24 N1 . . 118.31(12) ?
C24 C25 C26 . . 118.13(13) ?
C24 C25 H25 . . 120.9 ?
C26 C25 H25 . . 120.9 ?
C25 C26 C21 . . 120.34(13) ?
C25 C26 H26 . . 119.8 ?
C21 C26 H26 . . 119.8 ?
O4 N1 O3 . . 122.88(12) ?
O4 N1 C24 . . 118.60(12) ?
O3 N1 C24 . . 118.51(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O2 . 1.3932(17) ?
C1 O1 . 1.4068(16) ?
C1 C21 . 1.5252(18) ?
C1 C2 . 1.5429(19) ?
O1 C3 . 1.4491(16) ?
O2 H2 . 0.82(2) ?
C2 F1 . 1.3361(18) ?
C2 F2 . 1.3364(17) ?
C2 F3 . 1.3371(17) ?
C3 C11 . 1.500(2) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C11 C12 . 1.387(2) ?
C11 C16 . 1.392(2) ?
C12 C13 . 1.390(2) ?
C12 H12 . 0.95 ?
C13 C14 . 1.385(2) ?
C13 H13 . 0.95 ?
C14 C15 . 1.390(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.383(2) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C21 C22 . 1.3942(19) ?
C21 C26 . 1.3953(19) ?
C22 C23 . 1.386(2) ?
C22 H22 . 0.95 ?
C23 C24 . 1.384(2) ?
C23 H23 . 0.95 ?
C24 C25 . 1.384(2) ?
C24 N1 . 1.4672(18) ?
C25 C26 . 1.385(2) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
N1 O4 . 1.2286(16) ?
N1 O3 . 1.2330(17) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 O3 1_565 0.82(2) 2.18(2) 2.9904(15) 169.6(19) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 C1 O1 C3 . . . . -51.21(15) ?
C21 C1 O1 C3 . . . . 73.08(14) ?
C2 C1 O1 C3 . . . . -168.51(10) ?
O2 C1 C2 F1 . . . . -174.40(11) ?
O1 C1 C2 F1 . . . . -54.14(14) ?
C21 C1 C2 F1 . . . . 66.72(14) ?
O2 C1 C2 F2 . . . . -54.14(15) ?
O1 C1 C2 F2 . . . . 66.12(14) ?
C21 C1 C2 F2 . . . . -173.02(11) ?
O2 C1 C2 F3 . . . . 64.94(14) ?
O1 C1 C2 F3 . . . . -174.80(11) ?
C21 C1 C2 F3 . . . . -53.94(15) ?
C1 O1 C3 C11 . . . . -169.21(11) ?
O1 C3 C11 C12 . . . . -105.24(14) ?
O1 C3 C11 C16 . . . . 73.71(15) ?
C16 C11 C12 C13 . . . . 0.1(2) ?
C3 C11 C12 C13 . . . . 179.07(13) ?
C11 C12 C13 C14 . . . . -0.4(2) ?
C12 C13 C14 C15 . . . . 0.3(2) ?
C13 C14 C15 C16 . . . . 0.0(2) ?
C14 C15 C16 C11 . . . . -0.3(2) ?
C12 C11 C16 C15 . . . . 0.2(2) ?
C3 C11 C16 C15 . . . . -178.74(12) ?
O2 C1 C21 C22 . . . . 156.42(11) ?
O1 C1 C21 C22 . . . . 29.79(17) ?
C2 C1 C21 C22 . . . . -84.62(15) ?
O2 C1 C21 C26 . . . . -26.90(16) ?
O1 C1 C21 C26 . . . . -153.54(12) ?
C2 C1 C21 C26 . . . . 92.06(14) ?
C26 C21 C22 C23 . . . . 1.58(19) ?
C1 C21 C22 C23 . . . . 178.26(12) ?
C21 C22 C23 C24 . . . . -1.71(19) ?
C22 C23 C24 C25 . . . . 0.7(2) ?
C22 C23 C24 N1 . . . . -178.77(11) ?
C23 C24 C25 C26 . . . . 0.5(2) ?
N1 C24 C25 C26 . . . . 179.97(12) ?
C24 C25 C26 C21 . . . . -0.7(2) ?
C22 C21 C26 C25 . . . . -0.3(2) ?
C1 C21 C26 C25 . . . . -177.00(12) ?
C23 C24 N1 O4 . . . . 164.32(12) ?
C25 C24 N1 O4 . . . . -15.13(18) ?
C23 C24 N1 O3 . . . . -15.77(18) ?
C25 C24 N1 O3 . . . . 164.77(12) ?
