# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc20w2bb
_database_code_depnum_ccdc_archive 'CCDC 1873061'
_audit_update_record             
;
2018-10-12 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Cl2 O'
_chemical_formula_sum            'C12 H12 Cl2 O'
_chemical_formula_weight         243.12

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   10.442(2)
_cell_length_b                   4.8336(11)
_cell_length_c                   12.394(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.794(5)
_cell_angle_gamma                90
_cell_volume                     576.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7154
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      30.6

_exptl_crystal_description       lath
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.532
_shelx_estimated_absorpt_T_min   0.781
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
SADABS. G. M. Sheldrick. Apex II release 2010, Bruker AXS, Inc.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD with Bruker Apex II detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14723
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.253
_diffrn_reflns_theta_max         30.603
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3482
_reflns_number_gt                3308
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_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       'Apex II release 2010, Bruker AXS, Inc.'
_computing_cell_refinement       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'

_computing_structure_solution    
;

Sheldrick, G. M. (2015).  SHELXT.  Acta Cryst. A71, 3-8.

;
_computing_structure_refinement  'Shelxl-2016/6, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'SHELXL-2016/6, Sheldrick, G. M.'






_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+0.0770P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.00(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3482
_refine_ls_number_parameters     141
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0660
_refine_ls_wR_factor_gt          0.0648
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_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
C1 C 0.53963(19) 0.1802(4) 0.81306(15) 0.0119(3) Uani 1 1 d . . . . .
C2 C 0.43900(19) 0.2944(4) 0.71315(16) 0.0133(3) Uani 1 1 d . . . . .
H2 H 0.344886 0.235944 0.685929 0.016 Uiso 1 1 calc R U . . .
C3 C 0.48121(19) 0.4965(4) 0.65486(15) 0.0127(4) Uani 1 1 d . . . . .
C4 C 0.61800(19) 0.5831(4) 0.69259(15) 0.0121(3) Uani 1 1 d . . . . .
H4 H 0.643909 0.722176 0.650782 0.014 Uiso 1 1 calc R U . . .
C5 C 0.71787(18) 0.4638(4) 0.79293(14) 0.0098(3) Uani 1 1 d . . . . .
C6 C 0.67811(19) 0.2620(4) 0.85426(16) 0.0113(3) Uani 1 1 d . . . . .
H6 H 0.744604 0.181595 0.923135 0.014 Uiso 1 1 calc R U . . .
C7 C 0.86847(18) 0.5504(4) 0.82867(14) 0.0098(3) Uani 1 1 d . . . . .
H7 H 0.869174 0.743204 0.799631 0.012 Uiso 1 1 calc R U . . .
C8 C 0.94178(19) 0.3632(4) 0.76989(16) 0.0123(3) Uani 1 1 d . . . . .
H8A H 0.955269 0.177731 0.806484 0.015 Uiso 1 1 calc R U . . .
H8B H 0.881068 0.341700 0.686149 0.015 Uiso 1 1 calc R U . . .
C9 C 1.08086(19) 0.4740(4) 0.77926(15) 0.0132(4) Uani 1 1 d . . . . .
C10 C 1.0843(2) 0.6939(4) 0.69865(17) 0.0188(4) Uani 1 1 d . . . . .
H10 H 1.172397 0.773146 0.712080 0.023 Uiso 1 1 calc R U . . .
C11 C 0.9770(3) 0.7925(5) 0.6093(2) 0.0259(5) Uani 1 1 d . . . . .
H11A H 0.886676 0.720081 0.592166 0.031 Uiso 1 1 calc R U . . .
H11B H 0.990302 0.935707 0.562148 0.031 Uiso 1 1 calc R U . . .
C12 C 1.1989(2) 0.3782(4) 0.85985(18) 0.0192(4) Uani 1 1 d . . . . .
H12A H 1.285453 0.452066 0.865211 0.023 Uiso 1 1 calc R U . . .
H12B H 1.196432 0.235926 0.911914 0.023 Uiso 1 1 calc R U . . .
O1 O 0.94143(14) 0.5534(3) 0.95293(11) 0.0124(3) Uani 1 1 d . . . . .
Cl1 Cl 0.48933(5) -0.07054(9) 0.88942(4) 0.01559(10) Uani 1 1 d . . . . .
Cl2 Cl 0.35772(5) 0.65010(10) 0.53119(4) 0.02013(12) Uani 1 1 d . . . . .
H1O H 0.972(3) 0.416(8) 0.971(2) 0.034(9) Uiso 1 1 d . . . . .


_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
C1 C2 1.391(3) . ?
C1 C6 1.391(3) . ?
C1 Cl1 1.7392(18) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(3) . ?
C3 Cl2 1.7412(18) . ?
C4 C5 1.401(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(2) . ?
C5 C7 1.518(2) . ?
C6 H6 0.9500 . ?
C7 O1 1.430(2) . ?
C7 C8 1.539(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.510(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C12 1.333(3) . ?
C9 C10 1.468(3) . ?
C10 C11 1.322(3) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9500 . ?
C11 H11B 0.9500 . ?
C12 H12A 0.9500 . ?
C12 H12B 0.9500 . ?
O1 H1O 0.73(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_3
_geom_angle_publ_flag
C2 C1 C6 122.22(17) . . ?
C2 C1 Cl1 118.54(14) . . ?
C6 C1 Cl1 119.23(14) . . ?
C3 C2 C1 117.47(17) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C4 C3 C2 122.16(16) . . ?
C4 C3 Cl2 118.94(13) . . ?
C2 C3 Cl2 118.89(14) . . ?
C3 C4 C5 119.44(16) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 119.68(17) . . ?
C6 C5 C7 121.81(15) . . ?
C4 C5 C7 118.45(15) . . ?
C1 C6 C5 119.02(16) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
O1 C7 C5 112.12(14) . . ?
O1 C7 C8 111.15(14) . . ?
C5 C7 C8 110.42(14) . . ?
O1 C7 H7 107.6 . . ?
C5 C7 H7 107.6 . . ?
C8 C7 H7 107.6 . . ?
C9 C8 C7 113.28(14) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C12 C9 C10 120.14(18) . . ?
C12 C9 C8 121.12(17) . . ?
C10 C9 C8 118.73(16) . . ?
C11 C10 C9 126.5(2) . . ?
C11 C10 H10 116.7 . . ?
C9 C10 H10 116.7 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C9 C12 H12A 120.0 . . ?
C9 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
C7 O1 H1O 108(2) . . ?

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
C6 C1 C2 C3 -0.2(3) . . . . ?
Cl1 C1 C2 C3 179.06(14) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C1 C2 C3 Cl2 -178.62(14) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
Cl2 C3 C4 C5 179.09(14) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C3 C4 C5 C7 176.61(16) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
Cl1 C1 C6 C5 -179.79(13) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C7 C5 C6 C1 -176.25(16) . . . . ?
C6 C5 C7 O1 -36.7(2) . . . . ?
C4 C5 C7 O1 146.07(16) . . . . ?
C6 C5 C7 C8 87.9(2) . . . . ?
C4 C5 C7 C8 -89.40(19) . . . . ?
O1 C7 C8 C9 -67.75(19) . . . . ?
C5 C7 C8 C9 167.16(14) . . . . ?
C7 C8 C9 C12 99.6(2) . . . . ?
C7 C8 C9 C10 -79.6(2) . . . . ?
C12 C9 C10 C11 174.3(2) . . . . ?
C8 C9 C10 C11 -6.6(3) . . . . ?



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
O1 H1O O1 0.73(4) 2.03(4) 2.7555(14) 170(3) 2_747

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.055


