# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_AY51
_database_code_depnum_ccdc_archive 'CCDC 1436533'
_audit_update_record             
;
2015-11-12 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H13 Cl O3'
_chemical_formula_sum            'C13 H13 Cl O3'
_chemical_formula_weight         252.68

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                   7.1086(14)
_cell_length_b                   6.9376(14)
_cell_length_c                   12.442(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.573(3)
_cell_angle_gamma                90
_cell_volume                     611.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2882
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      24.61

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.305
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'SADABS; Bruker,2001'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6788
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.642
_diffrn_reflns_theta_max         28.383
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2841
_reflns_number_gt                2359
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_max     0.890
_reflns_Friedel_fraction_full    0.996

_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXL2014 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0476P)²+0.1148P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 880 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2841
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1040
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
C2 C -0.0675(4) 1.0034(5) 0.8974(3) 0.0548(8) Uani 1 1 d . . . . .
C3 C -0.0094(5) 1.1434(5) 0.8159(3) 0.0612(8) Uani 1 1 d . . . . .
H3A H -0.0290 1.2730 0.8421 0.073 Uiso 1 1 calc R U . . .
H3B H -0.0902 1.1269 0.7500 0.073 Uiso 1 1 calc R U . . .
C4 C 0.1936(5) 1.1238(4) 0.7901(3) 0.0553(7) Uani 1 1 d . . . . .
H4 H 0.2322 1.2377 0.7508 0.066 Uiso 1 1 calc R U . . .
C5 C 0.3121(4) 1.1053(5) 0.8957(3) 0.0626(9) Uani 1 1 d . . . . .
H5A H 0.4453 1.1093 0.8839 0.075 Uiso 1 1 calc R U . . .
H5B H 0.2846 1.2097 0.9440 0.075 Uiso 1 1 calc R U . . .
C6 C 0.2625(4) 0.9165(5) 0.9426(2) 0.0567(8) Uani 1 1 d . . . . .
H6 H 0.3334 0.9026 1.0130 0.068 Uiso 1 1 calc R U . . .
C7 C 0.3160(5) 0.7508(5) 0.8708(2) 0.0561(8) Uani 1 1 d . . . . .
H7A H 0.2168 0.6545 0.8675 0.067 Uiso 1 1 calc R U . . .
H7B H 0.4309 0.6908 0.9020 0.067 Uiso 1 1 calc R U . . .
C8 C 0.3460(4) 0.8194(4) 0.7569(2) 0.0444(6) Uani 1 1 d . . . . .
H8 H 0.4697 0.8817 0.7567 0.053 Uiso 1 1 calc R U . . .
C11 C 0.3343(4) 0.6571(4) 0.6765(2) 0.0466(6) Uani 1 1 d . . . . .
C12 C 0.1676(5) 0.6224(5) 0.6129(3) 0.0646(9) Uani 1 1 d . . . . .
H12 H 0.0630 0.6998 0.6216 0.077 Uiso 1 1 calc R U . . .
C13 C 0.1533(7) 0.4777(8) 0.5381(4) 0.0941(14) Uani 1 1 d . . . . .
H13 H 0.0406 0.4587 0.4962 0.113 Uiso 1 1 calc R U . . .
C14 C 0.3035(8) 0.3618(8) 0.5251(4) 0.1026(16) Uani 1 1 d . . . . .
H14 H 0.2931 0.2640 0.4739 0.123 Uiso 1 1 calc R U . . .
C15 C 0.4703(7) 0.3872(6) 0.5865(3) 0.0854(13) Uani 1 1 d . . . . .
H15 H 0.5727 0.3069 0.5777 0.103 Uiso 1 1 calc R U . . .
C16 C 0.4841(5) 0.5351(5) 0.6622(3) 0.0591(8) Uani 1 1 d . . . . .
Cl1 Cl 0.69655(13) 0.56808(16) 0.73964(9) 0.0843(4) Uani 1 1 d . . . . .
O1 O 0.0616(3) 0.9067(4) 0.95816(17) 0.0627(6) Uani 1 1 d . . . . .
O9 O 0.2023(3) 0.9550(3) 0.72366(15) 0.0520(5) Uani 1 1 d . . . . .
O10 O -0.2300(3) 0.9781(5) 0.9141(2) 0.0847(9) Uani 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
C2 O10 1.203(4) . ?
C2 O1 1.325(4) . ?
C2 C3 1.486(5) . ?
C3 C4 1.509(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O9 1.437(4) . ?
C4 C5 1.509(5) . ?
C4 H4 0.9800 . ?
C5 C6 1.487(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O1 1.458(4) . ?
C6 C7 1.523(4) . ?
C6 H6 0.9800 . ?
C7 C8 1.526(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O9 1.425(3) . ?
C8 C11 1.504(4) . ?
C8 H8 0.9800 . ?
C11 C16 1.383(4) . ?
C11 C12 1.392(5) . ?
C12 C13 1.367(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.356(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.370(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.391(5) . ?
C15 H15 0.9300 . ?
C16 Cl1 1.740(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
O10 C2 O1 117.3(3) . . ?
O10 C2 C3 122.5(3) . . ?
O1 C2 C3 120.2(3) . . ?
C2 C3 C4 114.1(3) . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
O9 C4 C3 106.3(3) . . ?
O9 C4 C5 112.6(3) . . ?
C3 C4 C5 107.4(3) . . ?
O9 C4 H4 110.1 . . ?
C3 C4 H4 110.1 . . ?
C5 C4 H4 110.1 . . ?
C6 C5 C4 106.4(3) . . ?
C6 C5 H5A 110.4 . . ?
C4 C5 H5A 110.4 . . ?
C6 C5 H5B 110.4 . . ?
C4 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
O1 C6 C5 111.0(2) . . ?
O1 C6 C7 109.6(3) . . ?
C5 C6 C7 110.9(3) . . ?
O1 C6 H6 108.4 . . ?
C5 C6 H6 108.4 . . ?
C7 C6 H6 108.4 . . ?
C6 C7 C8 111.7(3) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
O9 C8 C11 107.5(2) . . ?
O9 C8 C7 109.0(2) . . ?
C11 C8 C7 112.3(2) . . ?
O9 C8 H8 109.3 . . ?
C11 C8 H8 109.3 . . ?
C7 C8 H8 109.3 . . ?
C16 C11 C12 116.8(3) . . ?
C16 C11 C8 122.8(3) . . ?
C12 C11 C8 120.5(3) . . ?
C13 C12 C11 121.8(4) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C14 C13 C12 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.8(4) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C16 118.9(4) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C11 C16 C15 121.7(4) . . ?
C11 C16 Cl1 119.4(3) . . ?
C15 C16 Cl1 118.9(3) . . ?
C2 O1 C6 122.8(3) . . ?
C8 O9 C4 115.7(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
O10 C2 C3 C4 -167.5(3) . . . . ?
O1 C2 C3 C4 15.4(4) . . . . ?
C2 C3 C4 O9 74.9(3) . . . . ?
C2 C3 C4 C5 -46.0(4) . . . . ?
O9 C4 C5 C6 -49.1(3) . . . . ?
C3 C4 C5 C6 67.6(3) . . . . ?
C4 C5 C6 O1 -58.6(3) . . . . ?
C4 C5 C6 C7 63.5(3) . . . . ?
O1 C6 C7 C8 104.9(3) . . . . ?
C5 C6 C7 C8 -18.0(4) . . . . ?
C6 C7 C8 O9 -41.8(3) . . . . ?
C6 C7 C8 C11 -160.8(3) . . . . ?
O9 C8 C11 C16 158.3(3) . . . . ?
C7 C8 C11 C16 -81.8(3) . . . . ?
O9 C8 C11 C12 -22.2(4) . . . . ?
C7 C8 C11 C12 97.7(3) . . . . ?
C16 C11 C12 C13 -1.4(5) . . . . ?
C8 C11 C12 C13 179.1(4) . . . . ?
C11 C12 C13 C14 0.7(7) . . . . ?
C12 C13 C14 C15 0.3(9) . . . . ?
C13 C14 C15 C16 -0.5(8) . . . . ?
C12 C11 C16 C15 1.2(5) . . . . ?
C8 C11 C16 C15 -179.3(3) . . . . ?
C12 C11 C16 Cl1 -179.5(2) . . . . ?
C8 C11 C16 Cl1 0.0(4) . . . . ?
C14 C15 C16 C11 -0.3(6) . . . . ?
C14 C15 C16 Cl1 -179.6(4) . . . . ?
O10 C2 O1 C6 176.8(3) . . . . ?
C3 C2 O1 C6 -6.0(4) . . . . ?
C5 C6 O1 C2 28.5(4) . . . . ?
C7 C6 O1 C2 -94.3(3) . . . . ?
C11 C8 O9 C4 -178.8(2) . . . . ?
C7 C8 O9 C4 59.2(3) . . . . ?
C3 C4 O9 C8 -129.6(3) . . . . ?
C5 C4 O9 C8 -12.2(4) . . . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.037

