# 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_cu_180312E_0m
_database_code_depnum_ccdc_archive 'CCDC 1830066'
_audit_update_record             
;
2018-03-15 deposited with the CCDC.
2018-05-02 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         ?
_chemical_formula_sum            'C17 H18 Cl N O2'
_chemical_formula_weight         303.77

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'
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      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                   5.9758(3)
_cell_length_b                   8.5937(4)
_cell_length_c                   15.7695(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.352(2)
_cell_angle_gamma                90
_cell_volume                     808.45(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5164
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      70.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.118
_shelx_estimated_absorpt_T_min   0.677
_shelx_estimated_absorpt_T_max   0.816
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7618
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.807
_diffrn_reflns_theta_max         64.999
_diffrn_reflns_theta_full        64.999
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.946
_reflns_number_total             2587
_reflns_number_gt                2388
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_max     0.924
_reflns_Friedel_fraction_full    0.925

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0780P)²+0.0039P] 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 965 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.052(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2587
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_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 -0.3969(8) 0.7927(5) 0.5988(2) 0.0789(11) Uani 1 1 d . . . . .
C2 C -0.1955(8) 0.7196(6) 0.5896(2) 0.0856(12) Uani 1 1 d . . . . .
H2 H -0.1230 0.7303 0.5393 0.103 Uiso 1 1 calc R U . . .
C3 C -0.1015(6) 0.6311(5) 0.65434(18) 0.0680(9) Uani 1 1 d . . . . .
H3 H 0.0330 0.5798 0.6471 0.082 Uiso 1 1 calc R U . . .
C4 C -0.2044(5) 0.6167(3) 0.73098(17) 0.0495(7) Uani 1 1 d . . . . .
C5 C -0.4058(6) 0.6937(5) 0.7392(2) 0.0690(9) Uani 1 1 d . . . . .
H5 H -0.4772 0.6872 0.7899 0.083 Uiso 1 1 calc R U . . .
C6 C -0.5021(6) 0.7805(5) 0.6720(3) 0.0784(11) Uani 1 1 d . . . . .
H6 H -0.6387 0.8301 0.6776 0.094 Uiso 1 1 calc R U . . .
C7 C -0.0873(5) 0.5323(3) 0.80475(16) 0.0471(6) Uani 1 1 d . . . . .
H7 H 0.0164 0.4569 0.7819 0.057 Uiso 1 1 calc R U . . .
C8 C 0.0493(4) 0.6475(4) 0.85950(17) 0.0488(6) Uani 1 1 d . . . . .
H8A H -0.0530 0.7161 0.8870 0.059 Uiso 1 1 calc R U . . .
H8B H 0.1369 0.7110 0.8228 0.059 Uiso 1 1 calc R U . . .
C9 C 0.2079(5) 0.5737(4) 0.92767(17) 0.0503(6) Uani 1 1 d . . . . .
H9A H 0.1246 0.5045 0.9628 0.060 Uiso 1 1 calc R U . . .
H9B H 0.3212 0.5130 0.9010 0.060 Uiso 1 1 calc R U . . .
C10 C 0.3194(6) 0.7003(4) 0.9824(2) 0.0622(9) Uani 1 1 d . . . . .
H10A H 0.3675 0.7828 0.9456 0.075 Uiso 1 1 calc R U . . .
H10B H 0.2093 0.7439 1.0184 0.075 Uiso 1 1 calc R U . . .
C11 C 0.5186(5) 0.6463(4) 1.03771(18) 0.0501(6) Uani 1 1 d . . . . .
C12 C 0.6818(5) 0.6616(3) 1.18693(17) 0.0479(6) Uani 1 1 d . . . . .
C13 C 0.8794(5) 0.5820(4) 1.1778(2) 0.0587(7) Uani 1 1 d . . . . .
H13 H 0.9096 0.5390 1.1255 0.070 Uiso 1 1 calc R U . . .
C14 C 1.0319(6) 0.5663(5) 1.2462(2) 0.0738(10) Uani 1 1 d . . . . .
H14 H 1.1649 0.5125 1.2400 0.089 Uiso 1 1 calc R U . . .
C15 C 0.9884(7) 0.6304(5) 1.3243(2) 0.0792(11) Uani 1 1 d . . . . .
H15 H 1.0918 0.6194 1.3704 0.095 Uiso 1 1 calc R U . . .
C16 C 0.7915(8) 0.7103(6) 1.3334(2) 0.0786(11) Uani 1 1 d . . . . .
H16 H 0.7620 0.7550 1.3853 0.094 Uiso 1 1 calc R U . . .
C17 C 0.6368(6) 0.7237(4) 1.26414(19) 0.0621(8) Uani 1 1 d . . . . .
H17 H 0.5018 0.7753 1.2704 0.075 Uiso 1 1 calc R U . . .
Cl1 Cl -0.5164(3) 0.9061(2) 0.51685(7) 0.1352(7) Uani 1 1 d . . . . .
N2 N 0.5151(4) 0.6842(3) 1.12035(15) 0.0492(6) Uani 1 1 d . . . . .
H2A H 0.3941 0.7285 1.1349 0.059 Uiso 1 1 calc R U . . .
O1 O -0.2408(4) 0.4496(3) 0.85297(12) 0.0583(6) Uani 1 1 d . . . . .
H1 H -0.2595 0.4968 0.8972 0.087 Uiso 1 1 calc R U . . .
O2 O 0.6738(4) 0.5748(3) 1.00823(13) 0.0658(6) 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
C1 C6 1.351(6) . ?
C1 C2 1.372(6) . ?
C1 Cl1 1.738(4) . ?
C2 C3 1.367(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(5) . ?
C4 C7 1.508(4) . ?
C5 C6 1.392(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.416(3) . ?
C7 C8 1.520(4) . ?
C7 H7 0.9800 . ?
C8 C9 1.529(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.518(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.507(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O2 1.227(4) . ?
C11 N2 1.345(4) . ?
C12 C17 1.370(4) . ?
C12 C13 1.380(4) . ?
C12 N2 1.418(3) . ?
C13 C14 1.378(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.394(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
N2 H2A 0.8600 . ?
O1 H1 0.8200 . ?

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
C6 C1 C2 120.6(3) . . ?
C6 C1 Cl1 119.2(3) . . ?
C2 C1 Cl1 120.2(3) . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 C7 121.6(3) . . ?
C3 C4 C7 120.2(3) . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.0(4) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O1 C7 C4 111.7(2) . . ?
O1 C7 C8 111.4(2) . . ?
C4 C7 C8 109.5(2) . . ?
O1 C7 H7 108.0 . . ?
C4 C7 H7 108.0 . . ?
C8 C7 H7 108.0 . . ?
C7 C8 C9 114.8(3) . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.5 . . ?
C10 C9 C8 109.7(3) . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C11 C10 C9 114.5(3) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
O2 C11 N2 122.9(3) . . ?
O2 C11 C10 121.6(3) . . ?
N2 C11 C10 115.5(3) . . ?
C17 C12 C13 120.0(3) . . ?
C17 C12 N2 116.0(3) . . ?
C13 C12 N2 124.0(2) . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 119.5(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C12 C17 C16 120.5(3) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C11 N2 C12 129.4(2) . . ?
C11 N2 H2A 115.3 . . ?
C12 N2 H2A 115.3 . . ?
C7 O1 H1 109.5 . . ?

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 1.2(7) . . . . ?
Cl1 C1 C2 C3 179.7(4) . . . . ?
C1 C2 C3 C4 -1.6(7) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C2 C3 C4 C7 -173.8(4) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C7 C4 C5 C6 175.1(3) . . . . ?
C2 C1 C6 C5 0.2(7) . . . . ?
Cl1 C1 C6 C5 -178.3(3) . . . . ?
C4 C5 C6 C1 -1.3(6) . . . . ?
C5 C4 C7 O1 41.0(4) . . . . ?
C3 C4 C7 O1 -144.9(3) . . . . ?
C5 C4 C7 C8 -83.0(3) . . . . ?
C3 C4 C7 C8 91.2(3) . . . . ?
O1 C7 C8 C9 65.9(3) . . . . ?
C4 C7 C8 C9 -170.0(2) . . . . ?
C7 C8 C9 C10 -175.3(3) . . . . ?
C8 C9 C10 C11 -166.0(3) . . . . ?
C9 C10 C11 O2 52.2(5) . . . . ?
C9 C10 C11 N2 -128.8(3) . . . . ?
C17 C12 C13 C14 -0.6(5) . . . . ?
N2 C12 C13 C14 179.8(3) . . . . ?
C12 C13 C14 C15 -0.1(6) . . . . ?
C13 C14 C15 C16 -0.1(7) . . . . ?
C14 C15 C16 C17 1.0(7) . . . . ?
C13 C12 C17 C16 1.5(6) . . . . ?
N2 C12 C17 C16 -178.9(4) . . . . ?
C15 C16 C17 C12 -1.7(7) . . . . ?
O2 C11 N2 C12 4.2(5) . . . . ?
C10 C11 N2 C12 -174.7(3) . . . . ?
C17 C12 N2 C11 175.1(3) . . . . ?
C13 C12 N2 C11 -5.3(5) . . . . ?

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
C10 H10A O2 0.97 2.63 3.222(4) 119.8 2_657
C13 H13 O2 0.93 2.28 2.877(4) 121.5 .
N2 H2A O1 0.86 2.12 2.854(3) 142.6 2_557
O1 H1 O2 0.82 1.94 2.749(3) 170.0 1_455

_refine_diff_density_max         0.133
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.043



