# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ga_91109a_a
_database_code_depnum_ccdc_archive 'CCDC 1975866'
loop_
_audit_author_name
_audit_author_address
'Kejie Zhu'
;Department of Chemistry, Fudan University Shanghai 
China
;
_audit_update_record             
;
2020-01-07 deposited with the CCDC.	2021-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
(3aR,6aS)-3,3-dichloro-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 Cl2 O2'
_chemical_formula_weight         193.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

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'

_cell_length_a                   7.6662(15)
_cell_length_b                   9.925(2)
_cell_length_c                   10.643(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     809.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      59.20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    4.502
_shelx_estimated_absorpt_T_min   0.365
_shelx_estimated_absorpt_T_max   0.614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.485
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14618
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.302
_diffrn_reflns_theta_max         58.961
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1748
_reflns_number_gt                1621
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0214P)²+0.1099P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 642 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.037(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1748
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0605
_refine_ls_wR_factor_gt          0.0594
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.90607(8) 0.50257(7) 0.57726(5) 0.0592(2) Uani 1 1 d . . . . .
Cl2 Cl 0.87617(9) 0.33821(6) 0.35251(6) 0.0637(2) Uani 1 1 d . . . . .
O1 O 0.6398(2) 0.67018(16) 0.38964(16) 0.0576(4) Uani 1 1 d . . . . .
O2 O 0.8974(3) 0.6419(2) 0.29813(16) 0.0688(5) Uani 1 1 d . . . . .
C3 C 0.5889(3) 0.4511(2) 0.47231(18) 0.0454(5) Uani 1 1 d . . . . .
H3 H 0.574963 0.407650 0.554407 0.054 Uiso 1 1 calc R U . . .
C1 C 0.7840(3) 0.6017(2) 0.3650(2) 0.0458(5) Uani 1 1 d . . . . .
C2 C 0.7797(3) 0.4693(2) 0.43831(17) 0.0420(5) Uani 1 1 d . . . . .
C4 C 0.4753(4) 0.3874(3) 0.3746(2) 0.0578(6) Uani 1 1 d . . . . .
H4 H 0.496056 0.302708 0.340257 0.069 Uiso 1 1 calc R U . . .
C5 C 0.3435(4) 0.4640(3) 0.3428(3) 0.0707(8) Uani 1 1 d . . . . .
H5 H 0.259749 0.439647 0.283784 0.085 Uiso 1 1 calc R U . . .
C6 C 0.3429(4) 0.5956(4) 0.4124(3) 0.0774(9) Uani 1 1 d . . . . .
H6A H 0.250823 0.598071 0.474837 0.093 Uiso 1 1 calc R U . . .
H6B H 0.328654 0.670974 0.355257 0.093 Uiso 1 1 calc R U . . .
C7 C 0.5206(4) 0.5973(3) 0.4733(2) 0.0557(6) Uani 1 1 d . . . . .
H7 H 0.517847 0.635800 0.558074 0.067 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.799(2) . ?
Cl2 C2 1.753(2) . ?
O1 C1 1.324(3) . ?
O1 C7 1.467(3) . ?
O2 C1 1.192(3) . ?
C3 C4 1.497(3) . ?
C3 C2 1.517(3) . ?
C3 C7 1.543(3) . ?
C3 H3 0.9800 . ?
C1 C2 1.529(3) . ?
C4 C5 1.309(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.502(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7 0.9800 . ?

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_3
_geom_angle_publ_flag
C1 O1 C7 112.79(17) . . ?
C4 C3 C2 116.46(18) . . ?
C4 C3 C7 101.8(2) . . ?
C2 C3 C7 102.51(18) . . ?
C4 C3 H3 111.7 . . ?
C2 C3 H3 111.7 . . ?
C7 C3 H3 111.7 . . ?
O2 C1 O1 123.7(2) . . ?
O2 C1 C2 127.4(2) . . ?
O1 C1 C2 108.80(18) . . ?
C3 C2 C1 104.18(18) . . ?
C3 C2 Cl2 116.26(16) . . ?
C1 C2 Cl2 111.28(14) . . ?
C3 C2 Cl1 110.18(13) . . ?
C1 C2 Cl1 104.48(15) . . ?
Cl2 C2 Cl1 109.72(12) . . ?
C5 C4 C3 112.6(2) . . ?
C5 C4 H4 123.7 . . ?
C3 C4 H4 123.7 . . ?
C4 C5 C6 112.3(3) . . ?
C4 C5 H5 123.8 . . ?
C6 C5 H5 123.8 . . ?
C5 C6 C7 102.6(2) . . ?
C5 C6 H6A 111.2 . . ?
C7 C6 H6A 111.2 . . ?
C5 C6 H6B 111.2 . . ?
C7 C6 H6B 111.2 . . ?
H6A C6 H6B 109.2 . . ?
O1 C7 C6 107.9(2) . . ?
O1 C7 C3 104.38(18) . . ?
C6 C7 C3 107.0(2) . . ?
O1 C7 H7 112.4 . . ?
C6 C7 H7 112.4 . . ?
C3 C7 H7 112.4 . . ?

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
C7 O1 C1 O2 179.3(2) . . . . ?
C7 O1 C1 C2 -2.3(2) . . . . ?
C4 C3 C2 C1 84.2(2) . . . . ?
C7 C3 C2 C1 -26.0(2) . . . . ?
C4 C3 C2 Cl2 -38.7(2) . . . . ?
C7 C3 C2 Cl2 -148.80(15) . . . . ?
C4 C3 C2 Cl1 -164.26(17) . . . . ?
C7 C3 C2 Cl1 85.59(17) . . . . ?
O2 C1 C2 C3 -163.0(2) . . . . ?
O1 C1 C2 C3 18.6(2) . . . . ?
O2 C1 C2 Cl2 -37.0(3) . . . . ?
O1 C1 C2 Cl2 144.66(16) . . . . ?
O2 C1 C2 Cl1 81.4(2) . . . . ?
O1 C1 C2 Cl1 -97.01(18) . . . . ?
C2 C3 C4 C5 -122.3(2) . . . . ?
C7 C3 C4 C5 -11.8(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C7 11.4(3) . . . . ?
C1 O1 C7 C6 -128.3(2) . . . . ?
C1 O1 C7 C3 -14.7(3) . . . . ?
C5 C6 C7 O1 93.7(3) . . . . ?
C5 C6 C7 C3 -18.1(3) . . . . ?
C4 C3 C7 O1 -95.9(2) . . . . ?
C2 C3 C7 O1 24.9(2) . . . . ?
C4 C3 C7 C6 18.3(3) . . . . ?
C2 C3 C7 C6 139.1(2) . . . . ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.030



