# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_z
_database_code_depnum_ccdc_archive 'CCDC 1494872'
_audit_update_record             
;
2016-07-20 deposited with the CCDC.
2016-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 Cl O'
_chemical_formula_weight         296.78

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.8280(6)
_cell_length_b                   8.2327(8)
_cell_length_c                   16.8844(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.492(3)
_cell_angle_gamma                90.00
_cell_volume                     801.23(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5249
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.03

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8957
_exptl_absorpt_correction_T_max  0.9459
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9335
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2789
_reflns_number_gt                2598
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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     
'calc w=1/[σ²(Fo²)+(0.0462P)²+0.0645P] 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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_number_reflns         2789
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.80066(11) 0.70788(12) 0.00938(4) 0.1168(3) Uani 1 1 d . . .
O1 O 0.3764(3) 1.29025(18) -0.61777(8) 0.0807(4) Uani 1 1 d . . .
C1 C 0.4669(3) 0.9809(2) -0.16465(10) 0.0631(4) Uani 1 1 d . . .
H1A H 0.4973 1.0735 -0.1929 0.076 Uiso 1 1 calc R . .
C2 C 0.6355(3) 0.9213(3) -0.10645(11) 0.0700(5) Uani 1 1 d . . .
H2A H 0.7786 0.9729 -0.0950 0.084 Uiso 1 1 calc R . .
C3 C 0.5882(3) 0.7836(3) -0.06536(10) 0.0722(5) Uani 1 1 d . . .
C4 C 0.3798(3) 0.7070(3) -0.08092(11) 0.0758(5) Uani 1 1 d . . .
H4A H 0.3499 0.6150 -0.0521 0.091 Uiso 1 1 calc R . .
C5 C 0.2137(3) 0.7675(2) -0.13991(11) 0.0654(4) Uani 1 1 d . . .
H5A H 0.0721 0.7140 -0.1515 0.078 Uiso 1 1 calc R . .
C6 C 0.2524(3) 0.90608(19) -0.18232(9) 0.0529(3) Uani 1 1 d . . .
C7 C 0.1521(3) 1.26339(19) -0.39472(10) 0.0565(4) Uani 1 1 d . . .
C8 C 0.0475(3) 1.3626(2) -0.45653(11) 0.0646(4) Uani 1 1 d . . .
H8A H -0.0785 1.4264 -0.4483 0.077 Uiso 1 1 calc R . .
C9 C 0.1257(3) 1.3686(2) -0.52950(11) 0.0677(5) Uani 1 1 d . . .
H9A H 0.0504 1.4343 -0.5700 0.081 Uiso 1 1 calc R . .
C10 C 0.3144(3) 1.2782(2) -0.54275(10) 0.0603(4) Uani 1 1 d . . .
C11 C 0.4266(3) 1.1820(2) -0.48191(11) 0.0645(4) Uani 1 1 d . . .
H11A H 0.5562 1.1218 -0.4900 0.077 Uiso 1 1 calc R . .
C12 C 0.3458(3) 1.1756(2) -0.40937(10) 0.0635(4) Uani 1 1 d . . .
H12A H 0.4229 1.1107 -0.3689 0.076 Uiso 1 1 calc R . .
C13 C 0.5661(4) 1.1959(3) -0.63558(13) 0.0859(6) Uani 1 1 d . . .
H13A H 0.5911 1.2171 -0.6896 0.129 Uiso 1 1 calc R . .
H13B H 0.5325 1.0827 -0.6299 0.129 Uiso 1 1 calc R . .
H13C H 0.7031 1.2240 -0.5993 0.129 Uiso 1 1 calc R . .
C14 C 0.0679(3) 0.9694(2) -0.24371(9) 0.0591(4) Uani 1 1 d . . .
H14A H -0.0608 0.9031 -0.2580 0.071 Uiso 1 1 calc R . .
C15 C 0.0675(3) 1.1095(2) -0.28004(11) 0.0616(4) Uani 1 1 d . . .
C16 C 0.0584(3) 1.2481(2) -0.31827(10) 0.0618(4) Uani 1 1 d . . .
C17 C -0.0581(4) 1.3944(3) -0.28670(14) 0.0823(6) Uani 1 1 d . . .
H17A H 0.0399 1.4886 -0.2900 0.099 Uiso 1 1 calc R . .
H17B H -0.2035 1.4141 -0.3214 0.099 Uiso 1 1 calc R . .
C18 C -0.1058(5) 1.3798(3) -0.20450(16) 0.0958(7) Uani 1 1 d . . .
H18A H 0.0211 1.3548 -0.1663 0.115 Uiso 1 1 calc R . .
C19 C -0.2985(6) 1.3969(4) -0.1783(2) 0.1172(9) Uani 1 1 d . . .
H19C H -0.4321 1.4220 -0.2134 0.141 Uiso 1 1 calc R . .
H19A H -0.3055 1.3842 -0.1239 0.141 Uiso 1 1 calc R . .


_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 C3 1.747(2) . ?
O1 C10 1.371(2) . ?
O1 C13 1.419(3) . ?
C1 C2 1.374(3) . ?
C1 C6 1.386(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.378(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.359(3) . ?
C4 C5 1.376(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.383(2) . ?
C5 H5A 0.9300 . ?
C6 C14 1.474(2) . ?
C7 C8 1.393(2) . ?
C7 C12 1.393(2) . ?
C7 C16 1.479(2) . ?
C8 C9 1.376(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.373(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.383(2) . ?
C11 C12 1.377(2) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.306(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.308(3) . ?
C16 C17 1.518(3) . ?
C17 C18 1.460(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.275(4) . ?
C18 H18A 0.9300 . ?
C19 H19C 0.9300 . ?
C19 H19A 0.9300 . ?

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
C10 O1 C13 118.42(15) . . ?
C2 C1 C6 121.52(16) . . ?
C2 C1 H1A 119.2 . . ?
C6 C1 H1A 119.2 . . ?
C1 C2 C3 118.59(18) . . ?
C1 C2 H2A 120.7 . . ?
C3 C2 H2A 120.7 . . ?
C4 C3 C2 121.60(18) . . ?
C4 C3 Cl1 119.45(15) . . ?
C2 C3 Cl1 118.94(16) . . ?
C3 C4 C5 119.03(17) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C4 C5 C6 121.47(18) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C5 C6 C1 117.79(16) . . ?
C5 C6 C14 119.85(16) . . ?
C1 C6 C14 122.36(15) . . ?
C8 C7 C12 116.58(16) . . ?
C8 C7 C16 121.79(15) . . ?
C12 C7 C16 121.61(14) . . ?
C9 C8 C7 121.73(16) . . ?
C9 C8 H8A 119.1 . . ?
C7 C8 H8A 119.1 . . ?
C10 C9 C8 120.35(15) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
O1 C10 C9 115.97(15) . . ?
O1 C10 C11 124.58(16) . . ?
C9 C10 C11 119.45(16) . . ?
C12 C11 C10 119.76(16) . . ?
C12 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
C11 C12 C7 122.08(15) . . ?
C11 C12 H12A 119.0 . . ?
C7 C12 H12A 119.0 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C6 126.40(16) . . ?
C15 C14 H14A 116.8 . . ?
C6 C14 H14A 116.8 . . ?
C14 C15 C16 177.5(2) . . ?
C15 C16 C7 120.77(15) . . ?
C15 C16 C17 120.44(16) . . ?
C7 C16 C17 118.74(15) . . ?
C18 C17 C16 115.24(18) . . ?
C18 C17 H17A 108.5 . . ?
C16 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
C16 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C19 C18 C17 128.5(3) . . ?
C19 C18 H18A 115.7 . . ?
C17 C18 H18A 115.7 . . ?
C18 C19 H19C 120.0 . . ?
C18 C19 H19A 120.0 . . ?
H19C C19 H19A 120.0 . . ?

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
C6 C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C2 C3 Cl1 -179.48(14) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
Cl1 C3 C4 C5 -179.95(14) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C4 C5 C6 C1 1.3(2) . . . . ?
C4 C5 C6 C14 -178.47(16) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C1 C6 C14 179.06(16) . . . . ?
C12 C7 C8 C9 2.5(3) . . . . ?
C16 C7 C8 C9 -175.69(16) . . . . ?
C7 C8 C9 C10 -1.3(3) . . . . ?
C13 O1 C10 C9 -178.22(17) . . . . ?
C13 O1 C10 C11 1.2(3) . . . . ?
C8 C9 C10 O1 178.87(17) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
O1 C10 C11 C12 -178.24(17) . . . . ?
C9 C10 C11 C12 1.1(3) . . . . ?
C10 C11 C12 C7 0.2(3) . . . . ?
C8 C7 C12 C11 -1.9(3) . . . . ?
C16 C7 C12 C11 176.29(16) . . . . ?
C5 C6 C14 C15 169.74(17) . . . . ?
C1 C6 C14 C15 -10.0(3) . . . . ?
C6 C14 C15 C16 178(100) . . . . ?
C14 C15 C16 C7 -88(4) . . . . ?
C14 C15 C16 C17 89(4) . . . . ?
C8 C7 C16 C15 144.28(18) . . . . ?
C12 C7 C16 C15 -33.9(2) . . . . ?
C8 C7 C16 C17 -33.1(2) . . . . ?
C12 C7 C16 C17 148.76(18) . . . . ?
C15 C16 C17 C18 13.8(3) . . . . ?
C7 C16 C17 C18 -168.80(19) . . . . ?
C16 C17 C18 C19 -125.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.027
