# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_data
_database_code_depnum_ccdc_archive 'CCDC 1837613'
_audit_update_record             
;
2018-04-17 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 Cl N2 O2'
_chemical_formula_sum            'C19 H21 Cl N2 O2'
_chemical_formula_weight         344.83

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'
N N 0.0311 0.0180 '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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.2234(2)
_cell_length_b                   10.9322(2)
_cell_length_c                   17.6251(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1777.17(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    250.0(1)
_cell_measurement_reflns_used    10818
_cell_measurement_theta_min      4.7400
_cell_measurement_theta_max      71.6950

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    2.007
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.71339
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250.0(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            26755
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.760
_diffrn_reflns_theta_max         71.882
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3479
_reflns_number_gt                3246
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_max     0.985
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0629P)²+0.2849P] 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 1288 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(6)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3479
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_restrained_S_all      0.970
_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
Cl1 Cl 0.03319(8) 0.58935(8) 0.52922(4) 0.0640(2) Uani 1 1 d . . . . .
O1 O 0.2143(2) 0.4911(2) 0.17879(11) 0.0566(5) Uani 1 1 d . . . . .
O2 O 0.6815(2) 0.4575(2) 0.17483(13) 0.0645(6) Uani 1 1 d . . . . .
N1 N 0.2714(2) 0.7784(2) 0.08946(14) 0.0506(5) Uani 1 1 d . . . . .
N2 N 0.1072(2) 0.6391(2) 0.05581(12) 0.0484(5) Uani 1 1 d . . . . .
C1 C 0.2802(3) 0.4541(2) 0.36371(14) 0.0435(5) Uani 1 1 d . . . . .
H1 H 0.300332 0.377319 0.343593 0.052 Uiso 1 1 calc R U . . .
C2 C 0.1823(3) 0.4635(3) 0.42317(14) 0.0462(6) Uani 1 1 d . . . . .
H2 H 0.136458 0.394351 0.442312 0.055 Uiso 1 1 calc R U . . .
C3 C 0.1543(3) 0.5777(3) 0.45339(13) 0.0459(6) Uani 1 1 d . . . . .
C4 C 0.2196(3) 0.6804(3) 0.42465(16) 0.0513(6) Uani 1 1 d . . . . .
H4 H 0.199261 0.756913 0.445170 0.062 Uiso 1 1 calc R U . . .
C5 C 0.3162(3) 0.6694(2) 0.36476(16) 0.0480(6) Uani 1 1 d . . . . .
H5 H 0.359910 0.739313 0.345179 0.058 Uiso 1 1 calc R U . . .
C6 C 0.3492(2) 0.5559(2) 0.33332(13) 0.0381(5) Uani 1 1 d . . . . .
C7 C 0.4542(2) 0.5404(2) 0.26757(13) 0.0387(5) Uani 1 1 d . . . . .
H7 H 0.441125 0.456623 0.249081 0.046 Uiso 1 1 calc R U . . .
C8 C 0.6144(3) 0.5499(2) 0.29373(13) 0.0402(5) Uani 1 1 d . . . . .
H8 H 0.622411 0.500312 0.339860 0.048 Uiso 1 1 calc R U . . .
C9 C 0.6673(3) 0.6785(3) 0.31488(19) 0.0561(7) Uani 1 1 d . . . . .
H9A H 0.607355 0.710537 0.355520 0.067 Uiso 1 1 calc R U . . .
H9B H 0.656521 0.732116 0.271384 0.067 Uiso 1 1 calc R U . . .
C10 C 0.8264(3) 0.6785(3) 0.3404(2) 0.0660(8) Uani 1 1 d . . . . .
H10A H 0.856939 0.761786 0.350593 0.079 Uiso 1 1 calc R U . . .
H10B H 0.835638 0.632005 0.386984 0.079 Uiso 1 1 calc R U . . .
C11 C 0.9237(3) 0.6235(3) 0.2805(2) 0.0650(8) Uani 1 1 d . . . . .
H11A H 1.022885 0.622227 0.298846 0.078 Uiso 1 1 calc R U . . .
H11B H 0.920667 0.673660 0.235149 0.078 Uiso 1 1 calc R U . . .
C12 C 0.8758(3) 0.4937(3) 0.26123(18) 0.0574(7) Uani 1 1 d . . . . .
H12A H 0.935909 0.461311 0.220759 0.069 Uiso 1 1 calc R U . . .
H12B H 0.887204 0.441436 0.305320 0.069 Uiso 1 1 calc R U . . .
C13 C 0.7192(3) 0.4947(2) 0.23662(15) 0.0469(6) Uani 1 1 d . . . . .
C14 C 0.4160(3) 0.6245(2) 0.20108(14) 0.0439(6) Uani 1 1 d . . . . .
H14A H 0.405723 0.707765 0.219408 0.053 Uiso 1 1 calc R U . . .
H14B H 0.494220 0.623251 0.164325 0.053 Uiso 1 1 calc R U . . .
C15 C 0.2762(3) 0.5852(2) 0.16279(13) 0.0422(5) Uani 1 1 d . . . . .
C16 C 0.2195(3) 0.6679(3) 0.10337(13) 0.0425(5) Uani 1 1 d . . . . .
C17 C 0.1893(3) 0.8226(3) 0.03137(18) 0.0579(7) Uani 1 1 d . . . . .
H17 H 0.200319 0.899469 0.009443 0.070 Uiso 1 1 calc R U . . .
C18 C 0.0886(3) 0.7379(3) 0.01001(16) 0.0568(7) Uani 1 1 d . . . . .
H18 H 0.020354 0.746129 -0.028495 0.068 Uiso 1 1 calc R U . . .
C19 C 0.0250(3) 0.5249(3) 0.04944(17) 0.0615(7) Uani 1 1 d . . . . .
H19A H 0.089784 0.456609 0.054496 0.092 Uiso 1 1 calc R U . . .
H19B H -0.021804 0.521524 0.000830 0.092 Uiso 1 1 calc R U . . .
H19C H -0.046825 0.521570 0.088806 0.092 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 C3 1.746(3) . ?
O1 C15 1.210(3) . ?
O2 C13 1.213(3) . ?
N1 C16 1.322(4) . ?
N1 C17 1.362(4) . ?
N2 C18 1.359(4) . ?
N2 C16 1.369(3) . ?
N2 C19 1.465(4) . ?
C1 C2 1.387(4) . ?
C1 C6 1.389(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.382(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(4) . ?
C4 C5 1.387(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.520(3) . ?
C7 C14 1.531(3) . ?
C7 C8 1.551(3) . ?
C7 H7 0.9800 . ?
C8 C13 1.521(3) . ?
C8 C9 1.534(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.535(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.509(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.525(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.508(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C15 1.517(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.479(4) . ?
C17 C18 1.365(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
C16 N1 C17 105.2(2) . . ?
C18 N2 C16 106.0(2) . . ?
C18 N2 C19 124.5(2) . . ?
C16 N2 C19 129.4(2) . . ?
C2 C1 C6 122.0(2) . . ?
C2 C1 H1 119.0 . . ?
C6 C1 H1 119.0 . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 Cl1 120.3(2) . . ?
C2 C3 Cl1 118.7(2) . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 117.4(2) . . ?
C1 C6 C7 119.8(2) . . ?
C5 C6 C7 122.8(2) . . ?
C6 C7 C14 111.7(2) . . ?
C6 C7 C8 111.89(19) . . ?
C14 C7 C8 114.03(19) . . ?
C6 C7 H7 106.2 . . ?
C14 C7 H7 106.2 . . ?
C8 C7 H7 106.2 . . ?
C13 C8 C9 108.8(2) . . ?
C13 C8 C7 112.5(2) . . ?
C9 C8 C7 115.9(2) . . ?
C13 C8 H8 106.4 . . ?
C9 C8 H8 106.4 . . ?
C7 C8 H8 106.4 . . ?
C8 C9 C10 112.0(2) . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 111.4(3) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 110.7(3) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C11 109.6(2) . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
O2 C13 C12 122.0(3) . . ?
O2 C13 C8 123.0(2) . . ?
C12 C13 C8 114.9(2) . . ?
C15 C14 C7 111.5(2) . . ?
C15 C14 H14A 109.3 . . ?
C7 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C7 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
O1 C15 C16 121.2(2) . . ?
O1 C15 C14 122.6(2) . . ?
C16 C15 C14 116.3(2) . . ?
N1 C16 N2 111.7(2) . . ?
N1 C16 C15 124.2(2) . . ?
N2 C16 C15 124.1(2) . . ?
N1 C17 C18 110.1(3) . . ?
N1 C17 H17 124.9 . . ?
C18 C17 H17 124.9 . . ?
N2 C18 C17 106.8(2) . . ?
N2 C18 H18 126.6 . . ?
C17 C18 H18 126.6 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.032



