#------------------------------------------------------------------------------
#$Date: 2022-10-04 01:04:23 +0300 (Tue, 04 Oct 2022) $
#$Revision: 278327 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/77/1567706.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_1567706
loop_
_publ_author_name
'Stegbauer, Simone'
'Jandl, Christian'
'Bach, Thorsten'
_publ_section_title
;
 Chiral Lewis acid catalysis in a visible light-triggered
 cycloaddition/rearrangement cascade
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC03159K
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C17 H17 Cl O2'
_chemical_formula_sum            'C17 H17 Cl O2'
_chemical_formula_weight         288.76
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2022-03-12 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.320(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0803(3)
_cell_length_b                   8.5188(4)
_cell_length_c                   13.8407(6)
_cell_measurement_reflns_used    9872
_cell_measurement_temperature    123
_cell_measurement_theta_max      28.3564
_cell_measurement_theta_min      2.8077
_cell_volume                     716.89(6)
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_collection       'APEX III Control Software (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2004)'
_computing_structure_refinement
'SHELXL (Sheldrick, 2018), SHELXLE (Huebschle, 2011)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123
_diffrn_detector                 ' Bruker Photon-100 CMOS '
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker D8 Venture '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_radiation_monochromator  'Helios optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'TXS rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24577
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7193
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2, Bruker, 2016'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.099
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.015(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3555
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0247
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'W=1/[Σ²(FO²)+(0.0336P)²+0.1944P] WHERE P=(FO²+2FC²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0667
_reflns_number_gt                3527
_reflns_number_total             3555
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            d2sc03159k2.cif
_cod_data_source_block           compound_8m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1567706
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,1/2+y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl Uani 0.27122(9) 0.43045(6) 0.24174(3) 1.000 0.0320(1) d . . .
O1 O Uani 0.4782(2) 0.27439(17) 0.81897(9) 1.000 0.0285(4) d . . .
O2 O Uani 0.6609(2) 0.5767(2) 0.93251(11) 1.000 0.0387(5) d . . .
C1 C Uani 0.2875(3) 0.4225(2) 0.36688(10) 1.000 0.0218(4) d . . .
C2 C Uani 0.4626(3) 0.3394(2) 0.40973(12) 1.000 0.0236(5) d . . .
C3 C Uani 0.4744(3) 0.3288(2) 0.50845(12) 1.000 0.0206(4) d . . .
C4 C Uani 0.3142(2) 0.40077(17) 0.56858(11) 1.000 0.0153(4) d . . .
C5 C Uani 0.1430(3) 0.48770(19) 0.52354(11) 1.000 0.0164(4) d . . .
C6 C Uani 0.1322(3) 0.4964(2) 0.42134(12) 1.000 0.0210(4) d . . .
C7 C Uani 0.3179(3) 0.38587(17) 0.67133(11) 1.000 0.0155(4) d . . .
C8 C Uani 0.1616(2) 0.46009(17) 0.72705(10) 1.000 0.0150(4) d . . .
C9 C Uani -0.0048(3) 0.5502(2) 0.68059(11) 1.000 0.0192(4) d . . .
C10 C Uani -0.0151(3) 0.5633(2) 0.58234(12) 1.000 0.0215(4) d . . .
C11 C Uani 0.4847(3) 0.2776(2) 0.71689(12) 1.000 0.0253(4) d . . .
C12 C Uani 0.2572(3) 0.2725(2) 0.85427(13) 1.000 0.0271(5) d . . .
C13 C Uani 0.1559(2) 0.4335(2) 0.83571(10) 1.000 0.0174(4) d . . .
C14 C Uani 0.2711(2) 0.5628(2) 0.89809(11) 1.000 0.0164(4) d . . .
C15 C Uani 0.5134(3) 0.5730(2) 0.87416(13) 1.000 0.0234(5) d . . .
C16 C Uani 0.2373(3) 0.5315(2) 1.00574(12) 1.000 0.0248(5) d . . .
C17 C Uani 0.1797(3) 0.7267(2) 0.87320(13) 1.000 0.0225(4) d . . .
H2 H Uiso 0.57138 0.29114 0.37069 1.000 0.0280 c RU . .
H3 H Uiso 0.59217 0.27215 0.53738 1.000 0.0250 c RU . .
H6 H Uiso 0.01716 0.55365 0.39079 1.000 0.0250 c RU . .
H9 H Uiso -0.11140 0.60252 0.71879 1.000 0.0230 c RU . .
H10 H Uiso -0.12907 0.62342 0.55318 1.000 0.0260 c RU . .
H11A H Uiso 0.45974 0.16992 0.69225 1.000 0.0300 c RU . .
H11B H Uiso 0.63355 0.31053 0.69648 1.000 0.0300 c RU . .
H12A H Uiso 0.25688 0.24914 0.92434 1.000 0.0330 c RU . .
H12B H Uiso 0.17081 0.19044 0.82054 1.000 0.0330 c RU . .
H13 H Uiso -0.00182 0.42870 0.85553 1.000 0.0210 c RU . .
H15 H Uiso 0.55211 0.57669 0.80779 1.000 0.0280 c RU . .
H16A H Uiso 0.07978 0.52059 1.01883 1.000 0.0370 c RU . .
H16B H Uiso 0.29695 0.61931 1.04337 1.000 0.0370 c RU . .
H16C H Uiso 0.31346 0.43447 1.02405 1.000 0.0370 c RU . .
H17A H Uiso 0.21106 0.75100 0.80546 1.000 0.0340 c RU . .
H17B H Uiso 0.24949 0.80537 0.91493 1.000 0.0340 c RU . .
H17C H Uiso 0.02029 0.72794 0.88338 1.000 0.0340 c RU . .
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'
Cl Cl 0.1484 0.1585 ' 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 111.87(13) . . . yes
Cl1 C1 C2 118.63(13) . . . yes
Cl1 C1 C6 119.81(13) . . . yes
C2 C1 C6 121.56(14) . . . no
C1 C2 C3 119.25(16) . . . no
C2 C3 C4 121.48(16) . . . no
C3 C4 C5 118.08(14) . . . no
C3 C4 C7 122.48(14) . . . no
C5 C4 C7 119.43(13) . . . no
C4 C5 C6 119.70(15) . . . no
C4 C5 C10 118.88(14) . . . no
C6 C5 C10 121.42(16) . . . no
C1 C6 C5 119.90(16) . . . no
C4 C7 C8 120.57(14) . . . no
C4 C7 C11 118.56(14) . . . no
C8 C7 C11 120.70(14) . . . no
C7 C8 C9 119.03(13) . . . no
C7 C8 C13 120.24(12) . . . no
C9 C8 C13 120.51(12) . . . no
C8 C9 C10 121.56(15) . . . no
C5 C10 C9 120.47(16) . . . no
O1 C11 C7 114.05(14) . . . yes
O1 C12 C13 108.14(13) . . . yes
C8 C13 C12 106.80(12) . . . no
C8 C13 C14 115.37(13) . . . no
C12 C13 C14 111.19(12) . . . no
C13 C14 C15 110.68(12) . . . no
C13 C14 C16 110.69(13) . . . no
C13 C14 C17 110.80(12) . . . no
C15 C14 C16 111.07(13) . . . no
C15 C14 C17 104.43(13) . . . no
C16 C14 C17 109.01(13) . . . no
O2 C15 C14 125.22(16) . . . yes
C1 C2 H2 120.00 . . . no
C3 C2 H2 120.00 . . . no
C2 C3 H3 119.00 . . . no
C4 C3 H3 119.00 . . . no
C1 C6 H6 120.00 . . . no
C5 C6 H6 120.00 . . . no
C8 C9 H9 119.00 . . . no
C10 C9 H9 119.00 . . . no
C5 C10 H10 120.00 . . . no
C9 C10 H10 120.00 . . . no
O1 C11 H11A 109.00 . . . no
O1 C11 H11B 109.00 . . . no
C7 C11 H11A 109.00 . . . no
C7 C11 H11B 109.00 . . . no
H11A C11 H11B 108.00 . . . no
O1 C12 H12A 110.00 . . . no
O1 C12 H12B 110.00 . . . no
C13 C12 H12A 110.00 . . . no
C13 C12 H12B 110.00 . . . no
H12A C12 H12B 108.00 . . . no
C8 C13 H13 108.00 . . . no
C12 C13 H13 108.00 . . . no
C14 C13 H13 108.00 . . . no
O2 C15 H15 117.00 . . . no
C14 C15 H15 117.00 . . . no
C14 C16 H16A 109.00 . . . no
C14 C16 H16B 109.00 . . . no
C14 C16 H16C 109.00 . . . no
H16A C16 H16B 109.00 . . . no
H16A C16 H16C 109.00 . . . no
H16B C16 H16C 109.00 . . . no
C14 C17 H17A 109.00 . . . no
C14 C17 H17B 109.00 . . . no
C14 C17 H17C 109.00 . . . no
H17A C17 H17B 109.00 . . . no
H17A C17 H17C 109.00 . . . no
H17B C17 H17C 109.00 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7356(14) . . yes
O1 C11 1.414(2) . . yes
O1 C12 1.433(2) . . yes
O2 C15 1.204(2) . . yes
C1 C2 1.407(2) . . no
C1 C6 1.365(2) . . no
C2 C3 1.371(2) . . no
C3 C4 1.424(2) . . no
C4 C5 1.419(2) . . no
C4 C7 1.428(2) . . no
C5 C6 1.418(2) . . no
C5 C10 1.418(2) . . no
C7 C8 1.381(2) . . no
C7 C11 1.507(2) . . no
C8 C9 1.421(2) . . no
C8 C13 1.522(2) . . no
C9 C10 1.366(2) . . no
C12 C13 1.525(2) . . no
C13 C14 1.563(2) . . no
C14 C15 1.514(2) . . no
C14 C16 1.529(2) . . no
C14 C17 1.541(2) . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C6 H6 0.9500 . . no
C9 H9 0.9500 . . no
C10 H10 0.9500 . . no
C11 H11A 0.9900 . . no
C11 H11B 0.9900 . . no
C12 H12A 0.9900 . . no
C12 H12B 0.9900 . . no
C13 H13 1.0000 . . no
C15 H15 0.9500 . . no
C16 H16A 0.9800 . . no
C16 H16B 0.9800 . . no
C16 H16C 0.9800 . . no
C17 H17A 0.9800 . . no
C17 H17B 0.9800 . . no
C17 H17C 0.9800 . . no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C11 H11A Cl1 0.9900 2.7700 3.3566(18) 119.00 2_646 yes
C12 H12A O2 0.9900 2.5100 3.424(2) 153.00 2_647 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 O1 C11 C7 41.70(19) . . . . no
C11 O1 C12 C13 -70.93(17) . . . . no
Cl1 C1 C2 C3 -178.36(14) . . . . no
C6 C1 C2 C3 1.8(3) . . . . no
Cl1 C1 C6 C5 178.88(13) . . . . no
C2 C1 C6 C5 -1.3(3) . . . . no
C1 C2 C3 C4 -0.4(3) . . . . no
C2 C3 C4 C5 -1.4(2) . . . . no
C2 C3 C4 C7 177.33(16) . . . . no
C3 C4 C5 C6 1.9(2) . . . . no
C3 C4 C5 C10 -178.53(15) . . . . no
C7 C4 C5 C6 -176.87(15) . . . . no
C7 C4 C5 C10 2.7(2) . . . . no
C3 C4 C7 C8 178.78(15) . . . . no
C3 C4 C7 C11 -5.9(2) . . . . no
C5 C4 C7 C8 -2.5(2) . . . . no
C5 C4 C7 C11 172.82(15) . . . . no
C4 C5 C6 C1 -0.6(3) . . . . no
C10 C5 C6 C1 179.84(17) . . . . no
C4 C5 C10 C9 -1.2(3) . . . . no
C6 C5 C10 C9 178.37(17) . . . . no
C4 C7 C8 C9 0.7(2) . . . . no
C4 C7 C8 C13 175.25(13) . . . . no
C11 C7 C8 C9 -174.48(15) . . . . no
C11 C7 C8 C13 0.1(2) . . . . no
C4 C7 C11 O1 178.48(14) . . . . no
C8 C7 C11 O1 -6.2(2) . . . . no
C7 C8 C9 C10 0.8(2) . . . . no
C13 C8 C9 C10 -173.68(15) . . . . no
C7 C8 C13 C12 -26.20(18) . . . . no
C7 C8 C13 C14 97.94(16) . . . . no
C9 C8 C13 C12 148.26(14) . . . . no
C9 C8 C13 C14 -87.61(16) . . . . no
C8 C9 C10 C5 -0.6(3) . . . . no
O1 C12 C13 C8 59.96(15) . . . . no
O1 C12 C13 C14 -66.70(16) . . . . no
C8 C13 C14 C15 -61.48(16) . . . . no
C8 C13 C14 C16 174.93(12) . . . . no
C8 C13 C14 C17 53.89(15) . . . . no
C12 C13 C14 C15 60.33(17) . . . . no
C12 C13 C14 C16 -63.26(15) . . . . no
C12 C13 C14 C17 175.69(13) . . . . no
C13 C14 C15 O2 -132.39(18) . . . . no
C16 C14 C15 O2 -9.0(2) . . . . no
C17 C14 C15 O2 108.3(2) . . . . no
