# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_141013
_database_code_depnum_ccdc_archive 'CCDC 1530820'
_audit_update_record             
;
2017-02-03 deposited with the CCDC.
2017-09-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 Cl N2 O2'
_chemical_formula_sum            'C23 H15 Cl N2 O2'
_chemical_formula_weight         386.82

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'
N N 0.0061 0.0033 '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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.1098(6)
_cell_length_b                   10.3956(10)
_cell_length_c                   11.5000(16)
_cell_angle_alpha                88.824(10)
_cell_angle_beta                 77.369(10)
_cell_angle_gamma                87.304(7)
_cell_volume                     944.96(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2057
_cell_measurement_theta_min      3.1634
_cell_measurement_theta_max      28.8775

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9546
_exptl_absorpt_correction_T_max  0.9632
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5577
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3266
_reflns_number_gt                2726
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
omit -2 50
 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)+(0.0782P)²+9.9560P] 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     SHELXL
_refine_ls_extinction_coef       0.033(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3266
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1406
_refine_ls_R_factor_gt           0.1277
_refine_ls_wR_factor_ref         0.3431
_refine_ls_wR_factor_gt          0.3374
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_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
C1 C 0.1897(11) 0.4388(8) -0.1460(7) 0.0434(19) Uani 1 1 d . . .
H1 H 0.1224 0.3694 -0.1199 0.052 Uiso 1 1 calc R . .
C2 C 0.2187(13) 0.4798(11) -0.2638(8) 0.062(3) Uani 1 1 d . . .
H2 H 0.1713 0.4363 -0.3175 0.075 Uiso 1 1 calc R . .
C3 C 0.3136(13) 0.5812(12) -0.3025(8) 0.068(3) Uani 1 1 d . . .
H3 H 0.3327 0.6052 -0.3825 0.082 Uiso 1 1 calc R . .
C4 C 0.3844(11) 0.6512(10) -0.2240(8) 0.057(3) Uani 1 1 d . . .
H4 H 0.4476 0.7226 -0.2503 0.069 Uiso 1 1 calc R . .
C5 C 0.3572(10) 0.6107(9) -0.1057(8) 0.046(2) Uani 1 1 d . . .
H5 H 0.4023 0.6558 -0.0518 0.055 Uiso 1 1 calc R . .
C6 C 0.2647(9) 0.5048(7) -0.0675(7) 0.0349(17) Uani 1 1 d . . .
C7 C 0.2423(9) 0.4608(7) 0.0589(6) 0.0308(16) Uani 1 1 d . . .
C8 C 0.2178(9) 0.3333(7) 0.1067(6) 0.0329(16) Uani 1 1 d . . .
C9 C 0.2037(9) 0.3491(7) 0.2259(7) 0.0348(17) Uani 1 1 d . . .
H9 H 0.1872 0.2842 0.2836 0.042 Uiso 1 1 calc R . .
C10 C 0.2390(10) 0.2064(7) 0.0479(7) 0.0388(18) Uani 1 1 d . . .
C11 C 0.1337(10) 0.1004(7) 0.1060(7) 0.0353(17) Uani 1 1 d . . .
C12 C -0.0251(11) 0.1269(9) 0.1771(7) 0.047(2) Uani 1 1 d . . .
H12 H -0.0660 0.2116 0.1904 0.056 Uiso 1 1 calc R . .
C13 C -0.1225(13) 0.0260(10) 0.2282(9) 0.059(3) Uani 1 1 d . . .
H13 H -0.2294 0.0434 0.2757 0.070 Uiso 1 1 calc R . .
C14 C -0.0638(14) -0.0975(9) 0.2097(8) 0.058(3) Uani 1 1 d . . .
H14 H -0.1296 -0.1643 0.2458 0.070 Uiso 1 1 calc R . .
C15 C 0.0927(15) -0.1248(8) 0.1379(9) 0.060(3) Uani 1 1 d . . .
H15 H 0.1322 -0.2099 0.1250 0.072 Uiso 1 1 calc R . .
C16 C 0.1913(12) -0.0255(8) 0.0846(8) 0.048(2) Uani 1 1 d . . .
H16 H 0.2961 -0.0438 0.0346 0.058 Uiso 1 1 calc R . .
C17 C 0.3816(10) 0.7257(8) 0.2888(7) 0.045(2) Uani 1 1 d . . .
H17 H 0.4508 0.6794 0.2271 0.054 Uiso 1 1 calc R . .
C18 C 0.4133(11) 0.8533(8) 0.3060(7) 0.046(2) Uani 1 1 d . . .
H18 H 0.5048 0.8924 0.2575 0.055 Uiso 1 1 calc R . .
C19 C 0.3072(11) 0.9204(7) 0.3959(8) 0.0420(19) Uani 1 1 d . . .
C20 C 0.1719(11) 0.8640(8) 0.4697(7) 0.045(2) Uani 1 1 d . . .
H20 H 0.0996 0.9121 0.5286 0.054 Uiso 1 1 calc R . .
C21 C 0.1445(11) 0.7366(8) 0.4558(7) 0.0427(19) Uani 1 1 d . . .
H21 H 0.0574 0.6962 0.5078 0.051 Uiso 1 1 calc R . .
C22 C 0.2494(10) 0.6680(7) 0.3622(6) 0.0348(17) Uani 1 1 d . . .
C23 C 0.2166(10) 0.5293(8) 0.3577(6) 0.0370(17) Uani 1 1 d . . .
Cl1 Cl 0.3427(4) 1.0811(2) 0.4177(2) 0.0679(9) Uani 1 1 d . . .
N1 N 0.2180(8) 0.4750(6) 0.2457(5) 0.0343(14) Uani 1 1 d . . .
N2 N 0.2393(8) 0.5461(5) 0.1424(5) 0.0310(14) Uani 1 1 d . . .
O1 O 0.3458(9) 0.1901(6) -0.0432(6) 0.063(2) Uani 1 1 d . . .
O2 O 0.1864(9) 0.4589(6) 0.4432(5) 0.0543(17) 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 C2 1.385(12) . ?
C1 C6 1.400(11) . ?
C1 H1 0.9300 . ?
C2 C3 1.344(16) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(16) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.489(10) . ?
C7 N2 1.316(9) . ?
C7 C8 1.431(10) . ?
C8 C9 1.363(10) . ?
C8 C10 1.480(10) . ?
C9 N1 1.348(9) . ?
C9 H9 0.9300 . ?
C10 O1 1.213(9) . ?
C10 C11 1.483(11) . ?
C11 C16 1.377(11) . ?
C11 C12 1.385(11) . ?
C12 C13 1.385(12) . ?
C12 H12 0.9300 . ?
C13 C14 1.353(14) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(15) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(13) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.366(11) . ?
C17 C18 1.389(12) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(12) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(12) . ?
C19 Cl1 1.741(8) . ?
C20 C21 1.372(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.402(11) . ?
C21 H21 0.9300 . ?
C22 C23 1.482(11) . ?
C23 O2 1.203(9) . ?
C23 N1 1.415(9) . ?
N1 N2 1.368(8) . ?

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
C2 C1 C6 118.1(9) . . ?
C2 C1 H1 121.0 . . ?
C6 C1 H1 121.0 . . ?
C3 C2 C1 121.6(10) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 121.0(9) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.0(9) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C6 C5 C4 120.7(9) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.5(8) . . ?
C5 C6 C7 119.6(7) . . ?
C1 C6 C7 119.9(7) . . ?
N2 C7 C8 112.1(6) . . ?
N2 C7 C6 119.3(6) . . ?
C8 C7 C6 128.5(6) . . ?
C9 C8 C7 103.5(6) . . ?
C9 C8 C10 123.9(7) . . ?
C7 C8 C10 131.3(7) . . ?
N1 C9 C8 108.2(7) . . ?
N1 C9 H9 125.9 . . ?
C8 C9 H9 125.9 . . ?
O1 C10 C8 119.7(7) . . ?
O1 C10 C11 121.8(7) . . ?
C8 C10 C11 118.5(6) . . ?
C16 C11 C12 119.8(8) . . ?
C16 C11 C10 119.6(7) . . ?
C12 C11 C10 120.5(7) . . ?
C13 C12 C11 119.4(9) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.7(10) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.3(9) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 120.0(9) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 119.7(9) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C22 C17 C18 120.3(7) . . ?
C22 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 118.7(7) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C18 C19 C20 121.6(7) . . ?
C18 C19 Cl1 119.5(7) . . ?
C20 C19 Cl1 118.8(6) . . ?
C21 C20 C19 119.7(7) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 119.1(7) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C17 C22 C21 120.5(7) . . ?
C17 C22 C23 123.8(7) . . ?
C21 C22 C23 115.5(7) . . ?
O2 C23 N1 117.0(7) . . ?
O2 C23 C22 124.6(7) . . ?
N1 C23 C22 118.4(6) . . ?
C9 N1 N2 111.7(6) . . ?
C9 N1 C23 125.3(6) . . ?
N2 N1 C23 123.0(6) . . ?
C7 N2 N1 104.4(6) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.891
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.108
