# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_P17471
_database_code_depnum_ccdc_archive 'CCDC 1815141'
_audit_update_record             
;
2018-01-06 deposited with the CCDC.
2018-01-15 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         'C17 H19 Cl O4'
_chemical_formula_sum            'C17 H19 Cl O4'
_chemical_formula_weight         322.77


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   6.9832(6)
_cell_length_b                   8.5007(7)
_cell_length_c                   26.483(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1572.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9823
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      74.27

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.289
_shelx_estimated_absorpt_T_min   0.547
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6272
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            25120
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.337
_diffrn_reflns_theta_max         74.260
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3188
_reflns_number_gt                3089
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.999

_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       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT v8.38A (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT v8.38A (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+0.2378P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 1246 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.061(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3188
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0664
_refine_ls_wR_factor_gt          0.0656
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
O1 O 0.09283(18) 0.78055(15) 0.44186(5) 0.0232(3) Uani 1 1 d . . . . .
C1 C 0.0835(2) 0.6277(2) 0.43097(6) 0.0172(3) Uani 1 1 d . . . . .
O2 O -0.07128(18) 0.56373(16) 0.43128(5) 0.0244(3) Uani 1 1 d . . . . .
C2 C 0.2622(2) 0.53803(19) 0.41400(7) 0.0160(3) Uani 1 1 d . . . . .
C3 C 0.4511(2) 0.6200(2) 0.42895(7) 0.0193(4) Uani 1 1 d . . . . .
H3A H 0.477097 0.602296 0.465256 0.023 Uiso 1 1 calc R U . . .
H3B H 0.558491 0.574737 0.409320 0.023 Uiso 1 1 calc R U . . .
C4 C 0.4363(3) 0.7952(2) 0.41855(8) 0.0242(4) Uani 1 1 d . . . . .
H4A H 0.558258 0.847722 0.427406 0.029 Uiso 1 1 calc R U . . .
H4B H 0.410809 0.813285 0.382240 0.029 Uiso 1 1 calc R U . . .
C5 C 0.2756(3) 0.8620(2) 0.44978(7) 0.0257(4) Uani 1 1 d . . . . .
H5A H 0.310559 0.855097 0.485937 0.031 Uiso 1 1 calc R U . . .
H5B H 0.259436 0.974639 0.441287 0.031 Uiso 1 1 calc R U . . .
C6 C 0.2541(2) 0.3772(2) 0.43984(6) 0.0172(3) Uani 1 1 d . . . . .
O3 O 0.25963(19) 0.25233(14) 0.41858(5) 0.0243(3) Uani 1 1 d . . . . .
C7 C 0.2528(3) 0.2501(2) 0.52016(7) 0.0202(3) Uani 1 1 d . . . . .
H7A H 0.368863 0.188407 0.511872 0.024 Uiso 1 1 calc R U . . .
H7B H 0.138683 0.184338 0.513398 0.024 Uiso 1 1 calc R U . . .
O4 O 0.24619(17) 0.39390(14) 0.49012(5) 0.0192(3) Uani 1 1 d . . . . .
C8 C 0.2567(3) 0.3008(2) 0.57471(7) 0.0266(4) Uani 1 1 d . . . . .
H8A H 0.364532 0.372623 0.580174 0.040 Uiso 1 1 calc R U . . .
H8B H 0.271410 0.208187 0.596382 0.040 Uiso 1 1 calc R U . . .
H8C H 0.136664 0.354664 0.583019 0.040 Uiso 1 1 calc R U . . .
C9 C 0.2380(3) 0.5189(2) 0.35610(7) 0.0200(3) Uani 1 1 d . . . . .
H9A H 0.132930 0.443291 0.349660 0.024 Uiso 1 1 calc R U . . .
H9B H 0.199135 0.621449 0.341659 0.024 Uiso 1 1 calc R U . . .
C10 C 0.4143(3) 0.4629(2) 0.32905(8) 0.0206(3) Uani 1 1 d . . . . .
H10 H 0.481284 0.375099 0.342490 0.025 Uiso 1 1 calc R U . . .
C11 C 0.4812(3) 0.5296(2) 0.28738(7) 0.0220(4) Uani 1 1 d . . . . .
H11 H 0.411468 0.617138 0.274780 0.026 Uiso 1 1 calc R U . . .
C12 C 0.6521(2) 0.4825(2) 0.25858(7) 0.0207(4) Uani 1 1 d . . . . .
C13 C 0.7937(3) 0.3834(3) 0.27837(7) 0.0268(4) Uani 1 1 d . . . . .
H13 H 0.778159 0.341284 0.311346 0.032 Uiso 1 1 calc R U . . .
C14 C 0.9558(3) 0.3457(3) 0.25084(8) 0.0294(4) Uani 1 1 d . . . . .
H14 H 1.050461 0.278186 0.264797 0.035 Uiso 1 1 calc R U . . .
C15 C 0.9789(3) 0.4068(2) 0.20299(7) 0.0236(4) Uani 1 1 d . . . . .
Cl1 Cl 1.18557(7) 0.36058(7) 0.16920(2) 0.03444(14) Uani 1 1 d . . . . .
C16 C 0.8423(3) 0.5039(2) 0.18162(7) 0.0243(4) Uani 1 1 d . . . . .
H16 H 0.858884 0.544704 0.148509 0.029 Uiso 1 1 calc R U . . .
C17 C 0.6799(3) 0.5404(2) 0.20973(7) 0.0236(4) Uani 1 1 d . . . . .
H17 H 0.585069 0.606679 0.195285 0.028 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
O1 C1 1.333(2) . ?
O1 C5 1.467(2) . ?
C1 O2 1.210(2) . ?
C1 C2 1.530(2) . ?
C2 C6 1.530(2) . ?
C2 C3 1.543(2) . ?
C2 C9 1.551(2) . ?
C3 C4 1.518(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.505(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O3 1.202(2) . ?
C6 O4 1.340(2) . ?
C7 O4 1.459(2) . ?
C7 C8 1.508(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.502(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.326(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.472(3) . ?
C11 H11 0.9500 . ?
C12 C17 1.397(3) . ?
C12 C13 1.401(3) . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(3) . ?
C15 Cl1 1.7431(19) . ?
C16 C17 1.392(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

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 C5 122.26(14) . . ?
O2 C1 O1 118.72(16) . . ?
O2 C1 C2 120.46(16) . . ?
O1 C1 C2 120.61(15) . . ?
C1 C2 C6 106.47(13) . . ?
C1 C2 C3 113.40(14) . . ?
C6 C2 C3 108.67(14) . . ?
C1 C2 C9 104.69(14) . . ?
C6 C2 C9 110.14(14) . . ?
C3 C2 C9 113.22(14) . . ?
C4 C3 C2 109.75(14) . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 108.75(16) . . ?
C5 C4 H4A 109.9 . . ?
C3 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
O1 C5 C4 113.07(15) . . ?
O1 C5 H5A 109.0 . . ?
C4 C5 H5A 109.0 . . ?
O1 C5 H5B 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
O3 C6 O4 124.08(16) . . ?
O3 C6 C2 125.33(16) . . ?
O4 C6 C2 110.55(14) . . ?
O4 C7 C8 106.47(14) . . ?
O4 C7 H7A 110.4 . . ?
C8 C7 H7A 110.4 . . ?
O4 C7 H7B 110.4 . . ?
C8 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
C6 O4 C7 116.84(13) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C2 114.54(15) . . ?
C10 C9 H9A 108.6 . . ?
C2 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C2 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 123.40(17) . . ?
C11 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
C10 C11 C12 126.94(18) . . ?
C10 C11 H11 116.5 . . ?
C12 C11 H11 116.5 . . ?
C17 C12 C13 117.39(17) . . ?
C17 C12 C11 119.79(17) . . ?
C13 C12 C11 122.81(17) . . ?
C14 C13 C12 121.30(18) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C13 119.48(18) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 121.37(18) . . ?
C14 C15 Cl1 118.91(15) . . ?
C16 C15 Cl1 119.72(15) . . ?
C15 C16 C17 118.44(17) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C16 C17 C12 122.01(18) . . ?
C16 C17 H17 119.0 . . ?
C12 C17 H17 119.0 . . ?

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
C5 O1 C1 O2 170.67(16) . . . . ?
C5 O1 C1 C2 -14.5(2) . . . . ?
O2 C1 C2 C6 -45.3(2) . . . . ?
O1 C1 C2 C6 139.99(16) . . . . ?
O2 C1 C2 C3 -164.76(17) . . . . ?
O1 C1 C2 C3 20.5(2) . . . . ?
O2 C1 C2 C9 71.34(19) . . . . ?
O1 C1 C2 C9 -103.36(18) . . . . ?
C1 C2 C3 C4 -43.6(2) . . . . ?
C6 C2 C3 C4 -161.81(15) . . . . ?
C9 C2 C3 C4 75.47(19) . . . . ?
C2 C3 C4 C5 60.8(2) . . . . ?
C1 O1 C5 C4 32.0(2) . . . . ?
C3 C4 C5 O1 -54.7(2) . . . . ?
C1 C2 C6 O3 124.19(18) . . . . ?
C3 C2 C6 O3 -113.33(19) . . . . ?
C9 C2 C6 O3 11.2(2) . . . . ?
C1 C2 C6 O4 -57.84(17) . . . . ?
C3 C2 C6 O4 64.64(18) . . . . ?
C9 C2 C6 O4 -170.80(13) . . . . ?
O3 C6 O4 C7 2.6(2) . . . . ?
C2 C6 O4 C7 -175.38(13) . . . . ?
C8 C7 O4 C6 175.89(14) . . . . ?
C1 C2 C9 C10 168.24(15) . . . . ?
C6 C2 C9 C10 -77.66(18) . . . . ?
C3 C2 C9 C10 44.2(2) . . . . ?
C2 C9 C10 C11 -132.25(19) . . . . ?
C9 C10 C11 C12 -179.98(17) . . . . ?
C10 C11 C12 C17 165.5(2) . . . . ?
C10 C11 C12 C13 -16.1(3) . . . . ?
C17 C12 C13 C14 0.7(3) . . . . ?
C11 C12 C13 C14 -177.81(19) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C13 C14 C15 Cl1 179.04(16) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
Cl1 C15 C16 C17 -179.20(15) . . . . ?
C15 C16 C17 C12 0.2(3) . . . . ?
C13 C12 C17 C16 -0.8(3) . . . . ?
C11 C12 C17 C16 177.69(18) . . . . ?

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038

