# Electronic Supplementary Material (ESI) for MedChemComm.
# 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_exp_4271
_audit_block_doi                 10.5517/ccdc.csd.cc1myqbm
_database_code_depnum_ccdc_archive 'CCDC 1518111'
_audit_update_record             
;
2016-11-20 deposited with the CCDC.
2017-03-08 downloaded from the CCDC.
;
_audit_creation_date             2016-06-28
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H15 Cl N2 O3'
_chemical_formula_sum            'C17 H15 Cl N2 O3'
_chemical_formula_weight         330.76
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
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'
O O 0.0106 0.0060 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   8.7758(3)
_cell_length_b                   10.3761(4)
_cell_length_c                   16.7996(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1529.75(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3342
_cell_measurement_temperature    104.8
_cell_measurement_theta_max      29.1610
_cell_measurement_theta_min      3.2668
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6446
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.27
_diffrn_ambient_temperature      104.8
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   11.00   42.00   1.0000    1.8600
omega____ theta____ kappa____ phi______ frames
    -       21.1273  -49.0000  -46.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   31.00   1.0000    1.8600
omega____ theta____ kappa____ phi______ frames
    -       21.1273  -37.0000   90.0000 80

#__ type_ start__ end____ width___ exp.time_
  3 omega   -5.00   37.00   1.0000    1.8600
omega____ theta____ kappa____ phi______ frames
    -       21.1273   77.0000  -60.0000 42

#__ type_ start__ end____ width___ exp.time_
  4 omega  -12.00   22.00   1.0000    1.8600
omega____ theta____ kappa____ phi______ frames
    -      -15.8148  -90.0000  -30.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega  -84.00  -37.00   1.0000    1.8600
omega____ theta____ kappa____ phi______ frames
    -      -15.8148  -37.0000   60.0000 47
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0435064000
_diffrn_orient_matrix_UB_12      0.0556159000
_diffrn_orient_matrix_UB_13      -0.0092308000
_diffrn_orient_matrix_UB_21      -0.0220268000
_diffrn_orient_matrix_UB_22      -0.0282490000
_diffrn_orient_matrix_UB_23      -0.0367105000
_diffrn_orient_matrix_UB_31      -0.0644882000
_diffrn_orient_matrix_UB_32      -0.0278599000
_diffrn_orient_matrix_UB_33      0.0187524000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2832
_reflns_number_total             3009
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3009
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0289P)²+0.1821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0675
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.54661(5) 0.42905(5) 0.03455(3) 0.02105(12) Uani 1 1 d . . .
O3 O 0.73875(14) -0.15273(12) -0.38368(7) 0.0165(3) Uani 1 1 d . . .
N2 N 0.79907(15) -0.05553(16) -0.33475(8) 0.0152(3) Uani 1 1 d . . .
O1 O 0.67222(13) 0.25846(13) -0.35649(7) 0.0163(3) Uani 1 1 d . . .
O2 O 1.01124(13) 0.13705(13) -0.28173(7) 0.0186(3) Uani 1 1 d . . .
C3 C 0.80968(17) 0.07129(18) -0.46062(10) 0.0134(4) Uani 1 1 d . . .
C14 C 0.63690(18) 0.41440(19) -0.05785(10) 0.0153(4) Uani 1 1 d . . .
N1 N 0.82425(16) 0.26649(16) -0.32857(9) 0.0157(3) Uani 1 1 d . . .
C4 C 0.74112(19) 0.18354(19) -0.49086(10) 0.0148(4) Uani 1 1 d . . .
C5 C 0.6687(2) 0.28619(19) -0.44000(11) 0.0170(4) Uani 1 1 d . . .
H5A H 0.7220 0.3689 -0.4495 0.020 Uiso 1 1 calc R . .
H5B H 0.5613 0.2972 -0.4567 0.020 Uiso 1 1 calc R . .
C12 C 0.6565(2) 0.47475(18) -0.19437(10) 0.0160(4) Uani 1 1 d . . .
H12 H 0.6208 0.5235 -0.2385 0.019 Uiso 1 1 calc R . .
C6 C 0.86775(19) -0.02010(19) -0.51375(10) 0.0160(4) Uani 1 1 d . . .
H6 H 0.9172 -0.0947 -0.4935 0.019 Uiso 1 1 calc R . .
C2 C 0.82788(18) 0.04793(18) -0.37327(10) 0.0133(4) Uani 1 1 d . . .
C9 C 0.7304(2) 0.1991(2) -0.57328(11) 0.0196(4) Uani 1 1 d . . .
H9 H 0.6848 0.2749 -0.5942 0.023 Uiso 1 1 calc R . .
C10 C 0.86026(19) 0.38260(17) -0.28371(10) 0.0155(4) Uani 1 1 d . . .
H10A H 0.8330 0.4587 -0.3163 0.019 Uiso 1 1 calc R . .
H10B H 0.9716 0.3854 -0.2743 0.019 Uiso 1 1 calc R . .
C8 C 0.7847(2) 0.1061(2) -0.62511(11) 0.0214(4) Uani 1 1 d . . .
H8 H 0.7744 0.1175 -0.6810 0.026 Uiso 1 1 calc R . .
C15 C 0.7575(2) 0.32988(19) -0.06630(11) 0.0174(4) Uani 1 1 d . . .
H15 H 0.7913 0.2797 -0.0224 0.021 Uiso 1 1 calc R . .
C11 C 0.77909(19) 0.39186(17) -0.20447(10) 0.0134(4) Uani 1 1 d . . .
C1 C 0.89623(19) 0.15215(18) -0.32145(10) 0.0138(4) Uani 1 1 d . . .
C17 C 0.6885(2) -0.25648(19) -0.33383(11) 0.0192(4) Uani 1 1 d . . .
H17A H 0.6576 -0.3296 -0.3671 0.029 Uiso 1 1 calc R . .
H17B H 0.6016 -0.2278 -0.3017 0.029 Uiso 1 1 calc R . .
H17C H 0.7718 -0.2829 -0.2986 0.029 Uiso 1 1 calc R . .
C7 C 0.8545(2) -0.0039(2) -0.59513(11) 0.0200(4) Uani 1 1 d . . .
H7 H 0.8929 -0.0677 -0.6304 0.024 Uiso 1 1 calc R . .
C13 C 0.5849(2) 0.48786(19) -0.12108(11) 0.0181(4) Uani 1 1 d . . .
H13 H 0.5022 0.5459 -0.1145 0.022 Uiso 1 1 calc R . .
C16 C 0.8285(2) 0.31928(19) -0.13990(11) 0.0176(4) Uani 1 1 d . . .
H16 H 0.9118 0.2617 -0.1462 0.021 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
Cl1 C14 1.7494(17) . ?
O3 N2 1.4048(19) . ?
O3 C17 1.434(2) . ?
N2 C2 1.279(2) . ?
O1 N1 1.4167(17) . ?
O1 C5 1.432(2) . ?
O2 C1 1.220(2) . ?
C3 C4 1.406(3) . ?
C3 C6 1.398(2) . ?
C3 C2 1.496(2) . ?
C14 C15 1.382(3) . ?
C14 C13 1.385(3) . ?
N1 C10 1.456(2) . ?
N1 C1 1.349(2) . ?
C4 C5 1.506(3) . ?
C4 C9 1.397(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C12 H12 0.9500 . ?
C12 C11 1.388(2) . ?
C12 C13 1.389(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.382(2) . ?
C2 C1 1.512(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.384(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.513(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.390(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(3) . ?
C11 C16 1.390(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C7 H7 0.9500 . ?
C13 H13 0.9500 . ?
C16 H16 0.9500 . ?

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
N2 O3 C17 108.25(12) . . ?
C2 N2 O3 112.40(13) . . ?
N1 O1 C5 109.43(12) . . ?
C4 C3 C2 122.30(16) . . ?
C6 C3 C4 119.15(16) . . ?
C6 C3 C2 118.52(16) . . ?
C15 C14 Cl1 119.56(14) . . ?
C15 C14 C13 121.52(16) . . ?
C13 C14 Cl1 118.92(14) . . ?
O1 N1 C10 115.12(14) . . ?
C1 N1 O1 114.74(14) . . ?
C1 N1 C10 125.45(14) . . ?
C3 C4 C5 124.16(16) . . ?
C9 C4 C3 118.84(18) . . ?
C9 C4 C5 116.89(17) . . ?
O1 C5 C4 113.86(15) . . ?
O1 C5 H5A 108.8 . . ?
O1 C5 H5B 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.31(17) . . ?
C13 C12 H12 119.3 . . ?
C3 C6 H6 119.4 . . ?
C7 C6 C3 121.22(18) . . ?
C7 C6 H6 119.4 . . ?
N2 C2 C3 127.69(16) . . ?
N2 C2 C1 112.79(15) . . ?
C3 C2 C1 119.42(15) . . ?
C4 C9 H9 119.3 . . ?
C8 C9 C4 121.33(19) . . ?
C8 C9 H9 119.3 . . ?
N1 C10 H10A 108.8 . . ?
N1 C10 H10B 108.8 . . ?
N1 C10 C11 113.95(14) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C8 H8 120.1 . . ?
C9 C8 C7 119.74(17) . . ?
C7 C8 H8 120.1 . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 119.03(17) . . ?
C16 C15 H15 120.5 . . ?
C12 C11 C10 120.79(16) . . ?
C12 C11 C16 118.82(16) . . ?
C16 C11 C10 120.37(16) . . ?
O2 C1 N1 123.28(17) . . ?
O2 C1 C2 123.44(17) . . ?
N1 C1 C2 113.07(15) . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C7 C8 119.68(18) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C14 C13 C12 118.50(17) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C15 C16 C11 120.80(17) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?

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
Cl1 C14 C15 C16 -179.86(14) . . . . ?
Cl1 C14 C13 C12 -179.46(14) . . . . ?
O3 N2 C2 C3 -2.4(2) . . . . ?
O3 N2 C2 C1 -178.69(13) . . . . ?
N2 C2 C1 O2 55.6(2) . . . . ?
N2 C2 C1 N1 -129.43(16) . . . . ?
O1 N1 C10 C11 67.20(19) . . . . ?
O1 N1 C1 O2 -162.21(14) . . . . ?
O1 N1 C1 C2 22.8(2) . . . . ?
C3 C4 C5 O1 -1.4(2) . . . . ?
C3 C4 C9 C8 0.4(3) . . . . ?
C3 C6 C7 C8 1.2(3) . . . . ?
C3 C2 C1 O2 -121.05(19) . . . . ?
C3 C2 C1 N1 53.9(2) . . . . ?
C14 C15 C16 C11 -0.3(3) . . . . ?
N1 O1 C5 C4 69.47(19) . . . . ?
N1 C10 C11 C12 -104.76(19) . . . . ?
N1 C10 C11 C16 76.7(2) . . . . ?
C4 C3 C6 C7 -2.1(2) . . . . ?
C4 C3 C2 N2 134.29(19) . . . . ?
C4 C3 C2 C1 -49.6(2) . . . . ?
C4 C9 C8 C7 -1.4(3) . . . . ?
C5 O1 N1 C10 103.84(16) . . . . ?
C5 O1 N1 C1 -99.02(17) . . . . ?
C5 C4 C9 C8 -175.91(16) . . . . ?
C12 C11 C16 C15 -0.5(3) . . . . ?
C6 C3 C4 C5 177.34(16) . . . . ?
C6 C3 C4 C9 1.3(2) . . . . ?
C6 C3 C2 N2 -47.9(2) . . . . ?
C6 C3 C2 C1 128.19(17) . . . . ?
C2 C3 C4 C5 -4.9(3) . . . . ?
C2 C3 C4 C9 179.08(16) . . . . ?
C2 C3 C6 C7 -179.97(16) . . . . ?
C9 C4 C5 O1 174.77(15) . . . . ?
C9 C8 C7 C6 0.6(3) . . . . ?
C10 N1 C1 O2 -7.8(3) . . . . ?
C10 N1 C1 C2 177.22(15) . . . . ?
C10 C11 C16 C15 178.13(17) . . . . ?
C15 C14 C13 C12 0.3(3) . . . . ?
C11 C12 C13 C14 -1.1(3) . . . . ?
C1 N1 C10 C11 -87.1(2) . . . . ?
C17 O3 N2 C2 -171.16(15) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C13 C12 C11 C10 -177.42(16) . . . . ?
C13 C12 C11 C16 1.2(3) . . . . ?

