De-epimerizing DyKAT of β-lactones generated by isothiourea-catalysed enantioselective [2 + 2] cycloaddition.
Conboy, Aífe; Goodfellow, Alister S.; Kasten, Kevin; Dunne, Joanne; Cordes, David B.; Bühl, Michael; Smith, Andrew D.; Chemical science 15 (2024) 8896–8904; doi:10.1039/d4sc01410c

data_1571482
_publ_section_title
;
 De-epimerizing DyKAT of &#x3b2;-lactones generated by
 isothiourea-catalysed enantioselective [2 + 2] cycloaddition.
;
_journal_issue                   23
_journal_name_full               'Chemical science'
_journal_page_first              8896
_journal_page_last               8904
_journal_paper_doi               10.1039/d4sc01410c
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H22 Cl N3 O4, C H Cl3'
_chemical_formula_sum            'C23 H23 Cl4 N3 O4'
_chemical_formula_weight         547.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2hp63j
_audit_creation_date             2023-12-13
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-13 deposited with the CCDC.	2024-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.043(2)
_cell_length_b                   10.783(3)
_cell_length_c                   28.473(8)
_cell_measurement_reflns_used    4274
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.4
_cell_volume                     2469.4(12)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)
;
_computing_data_collection
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS P200K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
scan:
	Number of images: 324
	           Slice: -112.0000 - 50.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 160.0000
	             XTD: 50.0488
	          2theta: -22.1712
scan:
	Number of images: 346
	           Slice: -109.0000 - 64.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: -20.0000
	             XTD: 50.0488
	          2theta: -22.1712
scan:
	Number of images: 168
	           Slice: -88.0000 - -4.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 305.0000
	             XTD: 50.0488
	          2theta: -22.1712
scan:
	Number of images: 90
	           Slice: -102.0000 - -57.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 16.0000
	             XTD: 50.0488
	          2theta: -22.1712
scan:
	Number of images: 360
	           Slice: -112.0000 - 68.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 52.0000
	             XTD: 50.0488
	          2theta: -22.1712
scan:
	Number of images: 248
	           Slice: -79.5000 - 44.5000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 88.0000
	             XTD: 50.0488
	          2theta: -22.1712
;
_diffrn_measurement_device       'AFC10: Fixed \c 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.053152
_diffrn_orient_matrix_UB_12      -0.040637
_diffrn_orient_matrix_UB_13      -0.104798
_diffrn_orient_matrix_UB_21      -0.037052
_diffrn_orient_matrix_UB_22      0.071232
_diffrn_orient_matrix_UB_23      -0.046414
_diffrn_orient_matrix_UB_31      0.028481
_diffrn_orient_matrix_UB_32      0.019340
_diffrn_orient_matrix_UB_33      0.006946
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            32369
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.338
_diffrn_reflns_theta_min         2.369
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           66.0
_diffrn_source_power             3.0
_diffrn_source_type              'Rigaku FR-X'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.515
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1128
_exptl_crystal_preparation       Loop
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform/hexane/ethyl acetate'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1530 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4495
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0462
_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/[\s^2^(Fo^2^)+(0.0871P)^2^+1.3115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1390
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3977
_reflns_number_total             4495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc01410c2.cif
_cod_data_source_block           21
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1571481--1571482.cif.
;
_cod_original_cell_volume        2469.3(11)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1571482
_shelx_shelxl_version_number     2019/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-H1
 0.98 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C6(H6), C31(H31)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25)
3.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              22392