# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1481274'
_audit_update_record             
;
2016-05-26 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 Cl N O2'
_chemical_formula_weight         361.81

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'
N N 0.0061 0.0033 '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)/n  '

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

_cell_length_a                   11.366(4)
_cell_length_b                   11.305(4)
_cell_length_c                   14.788(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.536(6)
_cell_angle_gamma                90.00
_cell_volume                     1779.4(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3621
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      26.79

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8741
_exptl_absorpt_correction_T_max  0.9553
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8874
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3130
_reflns_number_gt                2489
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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     
'calc w=1/[σ²(Fo²)+(0.0808P)²+0.1750P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3130
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_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
Cl Cl 0.35125(5) 0.52820(5) -0.00275(5) 0.0823(2) Uani 1 1 d . . .
N1 N -0.11578(12) 0.60727(12) -0.14405(10) 0.0470(3) Uani 1 1 d . . .
C1 C 0.21577(16) 0.59508(16) 0.00091(14) 0.0533(4) Uani 1 1 d . . .
C2 C 0.22541(16) 0.67506(18) 0.07486(14) 0.0584(5) Uani 1 1 d . . .
H2B H 0.3029 0.6899 0.1225 0.070 Uiso 1 1 calc R . .
C3 C 0.10406(16) 0.57018(14) -0.06893(13) 0.0492(4) Uani 1 1 d . . .
H3A H 0.0996 0.5145 -0.1163 0.059 Uiso 1 1 calc R . .
C4 C 0.12013(15) 0.73136(16) 0.07674(12) 0.0510(4) Uani 1 1 d . . .
H4A H 0.1265 0.7839 0.1266 0.061 Uiso 1 1 calc R . .
C5 C -0.00567(14) 0.62933(13) -0.06925(11) 0.0404(4) Uani 1 1 d . . .
C6 C 0.00145(14) 0.71145(13) 0.00433(11) 0.0390(3) Uani 1 1 d . . .
C9 C -0.21481(15) 0.66804(14) -0.14583(11) 0.0453(4) Uani 1 1 d . . .
H9A H -0.2895 0.6534 -0.1966 0.054 Uiso 1 1 calc R . .
C10 C -0.21787(14) 0.75359(13) -0.07748(10) 0.0380(3) Uani 1 1 d . . .
C12 C -0.33811(13) 0.81733(13) -0.09198(10) 0.0395(4) Uani 1 1 d . . .
C13 C -0.37442(15) 0.90960(14) -0.15807(11) 0.0437(4) Uani 1 1 d . . .
C14 C -0.41574(16) 0.78657(15) -0.04186(12) 0.0507(4) Uani 1 1 d . . .
H14A H -0.3923 0.7249 0.0025 0.061 Uiso 1 1 calc R . .
C15 C -0.48564(16) 0.97049(16) -0.17047(13) 0.0542(4) Uani 1 1 d . . .
H15A H -0.5088 1.0339 -0.2131 0.065 Uiso 1 1 calc R . .
C16 C -0.52697(18) 0.84510(17) -0.05596(15) 0.0622(5) Uani 1 1 d . . .
H16A H -0.5786 0.8222 -0.0222 0.075 Uiso 1 1 calc R . .
C17 C -0.10933(14) 0.77454(13) 0.00000(10) 0.0372(3) Uani 1 1 d . . .
C18 C -0.10508(13) 0.86292(13) 0.07548(10) 0.0384(3) Uani 1 1 d . . .
C19 C -0.08611(17) 0.82979(15) 0.16979(12) 0.0510(4) Uani 1 1 d . . .
H19A H -0.0751 0.7502 0.1866 0.061 Uiso 1 1 calc R . .
C20 C -0.12083(15) 0.98217(14) 0.05316(11) 0.0416(4) Uani 1 1 d . . .
H20A H -0.1346 1.0064 -0.0098 0.050 Uiso 1 1 calc R . .
C21 C -0.08323(18) 0.91202(16) 0.23913(12) 0.0550(5) Uani 1 1 d . . .
H21A H -0.0709 0.8877 0.3019 0.066 Uiso 1 1 calc R . .
C22 C -0.09871(16) 1.03078(15) 0.21549(11) 0.0474(4) Uani 1 1 d . . .
C23 C -0.11662(16) 1.06611(14) 0.12225(12) 0.0458(4) Uani 1 1 d . . .
H23A H -0.1258 1.1459 0.1060 0.055 Uiso 1 1 calc R . .
C24 C -0.1163(3) 1.2265(2) 0.26709(17) 0.0901(8) Uani 1 1 d . . .
H24A H -0.1120 1.2688 0.3245 0.135 Uiso 1 1 calc R . .
H24B H -0.1977 1.2376 0.2185 0.135 Uiso 1 1 calc R . .
H24C H -0.0529 1.2558 0.2438 0.135 Uiso 1 1 calc R . .
C25 C -0.56104(17) 0.93730(17) -0.12004(14) 0.0593(5) Uani 1 1 d . . .
H25A H -0.6357 0.9776 -0.1294 0.071 Uiso 1 1 calc R . .
O1 O -0.09629(15) 1.10578(12) 0.28831(9) 0.0727(4) Uani 1 1 d . . .
O2 O -0.29716(13) 0.93864(13) -0.20661(10) 0.0671(4) Uani 1 1 d . . .
H2 H -0.3296(11) 0.997(2) -0.2457(13) 0.101 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
Cl C1 1.7332(17) . ?
N1 C9 1.311(2) . ?
N1 C5 1.371(2) . ?
C1 C3 1.356(3) . ?
C1 C2 1.393(3) . ?
C2 C4 1.364(2) . ?
C2 H2B 0.9300 . ?
C3 C5 1.414(2) . ?
C3 H3A 0.9300 . ?
C4 C6 1.415(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.411(2) . ?
C6 C17 1.429(2) . ?
C9 C10 1.408(2) . ?
C9 H9A 0.9300 . ?
C10 C17 1.378(2) . ?
C10 C12 1.492(2) . ?
C12 C14 1.381(2) . ?
C12 C13 1.389(2) . ?
C13 O2 1.355(2) . ?
C13 C15 1.394(2) . ?
C14 C16 1.376(2) . ?
C14 H14A 0.9300 . ?
C15 C25 1.371(3) . ?
C15 H15A 0.9300 . ?
C16 C25 1.370(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.486(2) . ?
C18 C20 1.385(2) . ?
C18 C19 1.386(2) . ?
C19 C21 1.376(2) . ?
C19 H19A 0.9300 . ?
C20 C23 1.383(2) . ?
C20 H20A 0.9300 . ?
C21 C22 1.383(3) . ?
C21 H21A 0.9300 . ?
C22 O1 1.363(2) . ?
C22 C23 1.380(2) . ?
C23 H23A 0.9300 . ?
C24 O1 1.401(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9300 . ?
O2 H2 0.8729 . ?

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
C9 N1 C5 117.06(13) . . ?
C3 C1 C2 121.83(15) . . ?
C3 C1 Cl 119.37(15) . . ?
C2 C1 Cl 118.78(14) . . ?
C4 C2 C1 119.38(16) . . ?
C4 C2 H2B 120.3 . . ?
C1 C2 H2B 120.3 . . ?
C1 C3 C5 119.58(16) . . ?
C1 C3 H3A 120.2 . . ?
C5 C3 H3A 120.2 . . ?
C2 C4 C6 121.35(17) . . ?
C2 C4 H4A 119.3 . . ?
C6 C4 H4A 119.3 . . ?
N1 C5 C6 122.08(13) . . ?
N1 C5 C3 118.10(14) . . ?
C6 C5 C3 119.79(14) . . ?
C5 C6 C4 118.02(14) . . ?
C5 C6 C17 118.86(14) . . ?
C4 C6 C17 123.05(14) . . ?
N1 C9 C10 125.64(14) . . ?
N1 C9 H9A 117.2 . . ?
C10 C9 H9A 117.2 . . ?
C17 C10 C9 118.33(14) . . ?
C17 C10 C12 122.96(13) . . ?
C9 C10 C12 118.71(13) . . ?
C14 C12 C13 118.58(14) . . ?
C14 C12 C10 121.76(14) . . ?
C13 C12 C10 119.65(13) . . ?
O2 C13 C12 117.82(14) . . ?
O2 C13 C15 122.47(15) . . ?
C12 C13 C15 119.69(15) . . ?
C16 C14 C12 121.56(16) . . ?
C16 C14 H14A 119.2 . . ?
C12 C14 H14A 119.2 . . ?
C25 C15 C13 120.29(16) . . ?
C25 C15 H15A 119.9 . . ?
C13 C15 H15A 119.9 . . ?
C25 C16 C14 119.49(17) . . ?
C25 C16 H16A 120.3 . . ?
C14 C16 H16A 120.3 . . ?
C10 C17 C6 117.98(14) . . ?
C10 C17 C18 121.58(13) . . ?
C6 C17 C18 120.40(13) . . ?
C20 C18 C19 117.67(14) . . ?
C20 C18 C17 120.55(13) . . ?
C19 C18 C17 121.78(14) . . ?
C21 C19 C18 121.47(16) . . ?
C21 C19 H19A 119.3 . . ?
C18 C19 H19A 119.3 . . ?
C18 C20 C23 121.60(14) . . ?
C18 C20 H20A 119.2 . . ?
C23 C20 H20A 119.2 . . ?
C19 C21 C22 119.99(15) . . ?
C19 C21 H21A 120.0 . . ?
C22 C21 H21A 120.0 . . ?
O1 C22 C23 124.34(16) . . ?
O1 C22 C21 116.01(15) . . ?
C23 C22 C21 119.64(15) . . ?
C20 C23 C22 119.62(15) . . ?
C20 C23 H23A 120.2 . . ?
C22 C23 H23A 120.2 . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C16 C25 C15 120.37(16) . . ?
C16 C25 H25A 119.8 . . ?
C15 C25 H25A 119.8 . . ?
C22 O1 C24 118.17(15) . . ?
C13 O2 H2 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.035
