# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1814286'
_audit_update_record             
;
2018-01-02 deposited with the CCDC.
2018-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H11 Cl N2 O2'
_chemical_formula_weight         346.76

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8729(11)
_cell_length_b                   9.3458(12)
_cell_length_c                   10.6991(14)
_cell_angle_alpha                68.9710(10)
_cell_angle_beta                 88.6400(10)
_cell_angle_gamma                69.7930(10)
_cell_volume                     772.05(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2307
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.99

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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            4634
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2687
_reflns_number_gt                2290
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0479P)²+0.1829P] 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         2687
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.00165(5) 1.19380(6) 0.05888(5) 0.05628(17) Uani 1 1 d . . .
O1 O 0.82342(15) 0.28858(16) 0.34055(14) 0.0534(3) Uani 1 1 d . . .
O2 O 0.51863(14) 0.67680(15) 0.47199(11) 0.0445(3) Uani 1 1 d . . .
N1 N 0.36048(16) 0.57092(18) 0.17478(14) 0.0401(3) Uani 1 1 d . . .
N2 N 0.61148(15) 0.53334(17) 0.27849(13) 0.0352(3) Uani 1 1 d . . .
C1 C 0.44802(18) 0.6193(2) 0.23334(16) 0.0350(4) Uani 1 1 d . . .
C2 C 0.68697(19) 0.3707(2) 0.28527(16) 0.0386(4) Uani 1 1 d . . .
C3 C 0.5893(2) 0.3154(2) 0.21867(16) 0.0386(4) Uani 1 1 d . . .
C4 C 0.6538(2) 0.1605(2) 0.21080(19) 0.0476(4) Uani 1 1 d . . .
H4A H 0.7567 0.0891 0.2528 0.057 Uiso 1 1 calc R . .
C5 C 0.5639(3) 0.1140(2) 0.1403(2) 0.0536(5) Uani 1 1 d . . .
H5A H 0.6059 0.0106 0.1351 0.064 Uiso 1 1 calc R . .
C6 C 0.4112(3) 0.2210(3) 0.0771(2) 0.0533(5) Uani 1 1 d . . .
H6A H 0.3532 0.1902 0.0267 0.064 Uiso 1 1 calc R . .
C7 C 0.3439(2) 0.3719(2) 0.08771(19) 0.0489(5) Uani 1 1 d . . .
H7A H 0.2398 0.4412 0.0470 0.059 Uiso 1 1 calc R . .
C8 C 0.4329(2) 0.4209(2) 0.16028(16) 0.0387(4) Uani 1 1 d . . .
C9 C 0.36374(19) 0.7741(2) 0.25556(16) 0.0364(4) Uani 1 1 d . . .
C10 C 0.23864(19) 0.8980(2) 0.15947(17) 0.0386(4) Uani 1 1 d . . .
H10A H 0.2174 0.8879 0.0790 0.046 Uiso 1 1 calc R . .
C11 C 0.14667(19) 1.0354(2) 0.18422(18) 0.0420(4) Uani 1 1 d . . .
C12 C 0.1715(2) 1.0523(2) 0.30441(19) 0.0484(4) Uani 1 1 d . . .
H12A H 0.1053 1.1438 0.3210 0.058 Uiso 1 1 calc R . .
C13 C 0.2963(2) 0.9310(2) 0.39912(18) 0.0464(4) Uani 1 1 d . . .
H13A H 0.3154 0.9407 0.4802 0.056 Uiso 1 1 calc R . .
C14 C 0.3926(2) 0.7954(2) 0.37394(16) 0.0391(4) Uani 1 1 d . . .
C15 C 0.6676(2) 0.6666(2) 0.42273(17) 0.0416(4) Uani 1 1 d . . .
C16 C 0.7677(3) 0.7239(2) 0.4719(2) 0.0554(5) Uani 1 1 d . . .
H16A H 0.7384 0.7641 0.5403 0.066 Uiso 1 1 calc R . .
C17 C 0.9110(3) 0.7213(3) 0.4190(2) 0.0640(6) Uani 1 1 d . . .
H17A H 0.9799 0.7577 0.4530 0.077 Uiso 1 1 calc R . .
C18 C 0.9528(2) 0.6649(3) 0.3160(2) 0.0596(6) Uani 1 1 d . . .
H18A H 1.0480 0.6670 0.2784 0.071 Uiso 1 1 calc R . .
C19 C 0.8537(2) 0.6051(2) 0.26800(19) 0.0480(4) Uani 1 1 d . . .
H19A H 0.8830 0.5656 0.1992 0.058 Uiso 1 1 calc R . .
C20 C 0.71050(19) 0.6043(2) 0.32281(16) 0.0383(4) 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
Cl1 C11 1.7422(17) . ?
O1 C2 1.213(2) . ?
O2 C14 1.395(2) . ?
O2 C15 1.396(2) . ?
N1 C1 1.292(2) . ?
N1 C8 1.390(2) . ?
N2 C1 1.390(2) . ?
N2 C2 1.408(2) . ?
N2 C20 1.444(2) . ?
C1 C9 1.483(2) . ?
C2 C3 1.459(2) . ?
C3 C4 1.394(2) . ?
C3 C8 1.394(2) . ?
C4 C5 1.377(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.384(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.374(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.404(2) . ?
C7 H7A 0.9300 . ?
C9 C14 1.393(2) . ?
C9 C10 1.393(2) . ?
C10 C11 1.376(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.382(3) . ?
C12 C13 1.378(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.376(2) . ?
C13 H13A 0.9300 . ?
C15 C20 1.379(2) . ?
C15 C16 1.381(2) . ?
C16 C17 1.376(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.375(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.384(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.388(2) . ?
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
C14 O2 C15 110.47(12) . . ?
C1 N1 C8 117.94(14) . . ?
C1 N2 C2 120.92(13) . . ?
C1 N2 C20 122.01(13) . . ?
C2 N2 C20 117.06(13) . . ?
N1 C1 N2 124.04(15) . . ?
N1 C1 C9 116.35(14) . . ?
N2 C1 C9 119.58(14) . . ?
O1 C2 N2 120.86(15) . . ?
O1 C2 C3 124.66(16) . . ?
N2 C2 C3 114.47(14) . . ?
C4 C3 C8 120.71(16) . . ?
C4 C3 C2 120.13(16) . . ?
C8 C3 C2 119.14(15) . . ?
C5 C4 C3 119.49(18) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
C4 C5 C6 120.08(18) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C7 C6 C5 121.09(18) . . ?
C7 C6 H6A 119.5 . . ?
C5 C6 H6A 119.5 . . ?
C6 C7 C8 119.66(18) . . ?
C6 C7 H7A 120.2 . . ?
C8 C7 H7A 120.2 . . ?
N1 C8 C3 122.20(15) . . ?
N1 C8 C7 118.91(15) . . ?
C3 C8 C7 118.87(16) . . ?
C14 C9 C10 118.18(15) . . ?
C14 C9 C1 123.08(15) . . ?
C10 C9 C1 118.42(14) . . ?
C11 C10 C9 119.71(15) . . ?
C11 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
C10 C11 C12 121.74(16) . . ?
C10 C11 Cl1 118.92(13) . . ?
C12 C11 Cl1 119.32(14) . . ?
C13 C12 C11 118.70(16) . . ?
C13 C12 H12A 120.6 . . ?
C11 C12 H12A 120.6 . . ?
C14 C13 C12 120.17(16) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C13 C14 C9 121.40(16) . . ?
C13 C14 O2 118.16(15) . . ?
C9 C14 O2 120.43(15) . . ?
C20 C15 C16 120.87(18) . . ?
C20 C15 O2 119.67(14) . . ?
C16 C15 O2 119.42(17) . . ?
C17 C16 C15 119.6(2) . . ?
C17 C16 H16A 120.2 . . ?
C15 C16 H16A 120.2 . . ?
C18 C17 C16 120.22(18) . . ?
C18 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
C17 C18 C19 120.2(2) . . ?
C17 C18 H18A 119.9 . . ?
C19 C18 H18A 119.9 . . ?
C18 C19 C20 119.83(19) . . ?
C18 C19 H19A 120.1 . . ?
C20 C19 H19A 120.1 . . ?
C15 C20 C19 119.20(16) . . ?
C15 C20 N2 120.79(15) . . ?
C19 C20 N2 119.97(16) . . ?

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
C8 N1 C1 N2 2.3(2) . . . . ?
C8 N1 C1 C9 -175.85(14) . . . . ?
C2 N2 C1 N1 -11.7(2) . . . . ?
C20 N2 C1 N1 169.51(15) . . . . ?
C2 N2 C1 C9 166.40(14) . . . . ?
C20 N2 C1 C9 -12.4(2) . . . . ?
C1 N2 C2 O1 -170.41(15) . . . . ?
C20 N2 C2 O1 8.4(2) . . . . ?
C1 N2 C2 C3 11.0(2) . . . . ?
C20 N2 C2 C3 -170.20(14) . . . . ?
O1 C2 C3 C4 -2.6(3) . . . . ?
N2 C2 C3 C4 175.98(15) . . . . ?
O1 C2 C3 C8 179.12(16) . . . . ?
N2 C2 C3 C8 -2.3(2) . . . . ?
C8 C3 C4 C5 2.4(3) . . . . ?
C2 C3 C4 C5 -175.90(16) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C7 -2.6(3) . . . . ?
C5 C6 C7 C8 1.9(3) . . . . ?
C1 N1 C8 C3 6.8(2) . . . . ?
C1 N1 C8 C7 -175.07(15) . . . . ?
C4 C3 C8 N1 175.09(15) . . . . ?
C2 C3 C8 N1 -6.6(2) . . . . ?
C4 C3 C8 C7 -3.0(2) . . . . ?
C2 C3 C8 C7 175.31(15) . . . . ?
C6 C7 C8 N1 -177.31(17) . . . . ?
C6 C7 C8 C3 0.8(3) . . . . ?
N1 C1 C9 C14 138.82(17) . . . . ?
N2 C1 C9 C14 -39.5(2) . . . . ?
N1 C1 C9 C10 -34.6(2) . . . . ?
N2 C1 C9 C10 147.16(15) . . . . ?
C14 C9 C10 C11 -0.8(2) . . . . ?
C1 C9 C10 C11 172.90(15) . . . . ?
C9 C10 C11 C12 -2.0(3) . . . . ?
C9 C10 C11 Cl1 176.44(12) . . . . ?
C10 C11 C12 C13 2.7(3) . . . . ?
Cl1 C11 C12 C13 -175.74(14) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 C9 -2.3(3) . . . . ?
C12 C13 C14 O2 179.20(16) . . . . ?
C10 C9 C14 C13 3.0(3) . . . . ?
C1 C9 C14 C13 -170.42(16) . . . . ?
C10 C9 C14 O2 -178.57(14) . . . . ?
C1 C9 C14 O2 8.0(2) . . . . ?
C15 O2 C14 C13 -116.13(17) . . . . ?
C15 O2 C14 C9 65.37(19) . . . . ?
C14 O2 C15 C20 -68.79(19) . . . . ?
C14 O2 C15 C16 109.15(17) . . . . ?
C20 C15 C16 C17 1.0(3) . . . . ?
O2 C15 C16 C17 -176.90(17) . . . . ?
C15 C16 C17 C18 1.3(3) . . . . ?
C16 C17 C18 C19 -2.3(3) . . . . ?
C17 C18 C19 C20 0.9(3) . . . . ?
C16 C15 C20 C19 -2.3(3) . . . . ?
O2 C15 C20 C19 175.57(15) . . . . ?
C16 C15 C20 N2 175.42(16) . . . . ?
O2 C15 C20 N2 -6.7(2) . . . . ?
C18 C19 C20 C15 1.4(3) . . . . ?
C18 C19 C20 N2 -176.42(16) . . . . ?
C1 N2 C20 C15 55.0(2) . . . . ?
C2 N2 C20 C15 -123.82(17) . . . . ?
C1 N2 C20 C19 -127.28(17) . . . . ?
C2 N2 C20 C19 53.9(2) . . . . ?

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 Cl1 0.93 2.89 3.6787(17) 142.9 2_575
C12 H12A O1 0.93 2.44 3.226(2) 141.8 1_465

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.036
