# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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data_z153

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 Cl N2 O2'
_chemical_formula_weight         340.80
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   7.3534(3)
_cell_length_b                   25.5994(8)
_cell_length_c                   9.1479(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.024(2)
_cell_angle_gamma                90.00
_cell_volume                     1715.41(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2374
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      53.37

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    2.078
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6694
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7617
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.45
_diffrn_reflns_theta_max         54.35
_reflns_number_total             3195
_reflns_number_gt                2650
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_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)+(0.1107P)²+0.0000P] 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       0.0031(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_number_reflns         3195
_refine_ls_number_parameters     438
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1637
_refine_ls_wR_factor_gt          0.1445
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_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 0.6951(8) 0.8206(2) 0.1623(6) 0.0782(14) Uani 1 1 d . . .
C2 C 0.8348(9) 0.7841(2) 0.1733(7) 0.0873(16) Uani 1 1 d . . .
C3 C 1.0103(9) 0.7982(2) 0.1384(8) 0.0956(18) Uani 1 1 d . . .
H3 H 1.1021 0.7731 0.1426 0.115 Uiso 1 1 calc R . .
C4 C 1.0485(8) 0.8482(2) 0.0983(7) 0.0828(16) Uani 1 1 d . . .
H4 H 1.1662 0.8570 0.0777 0.099 Uiso 1 1 calc R . .
C5 C 0.9100(8) 0.88646(19) 0.0880(6) 0.0729(13) Uani 1 1 d . . .
C6 C 0.7304(7) 0.87176(19) 0.1203(6) 0.0739(14) Uani 1 1 d . . .
C7 C 0.4916(11) 0.8109(4) 0.3418(10) 0.132(3) Uani 1 1 d . . .
H7A H 0.5769 0.7893 0.3996 0.198 Uiso 1 1 calc R . .
H7B H 0.3694 0.8000 0.3556 0.198 Uiso 1 1 calc R . .
H7C H 0.5077 0.8467 0.3718 0.198 Uiso 1 1 calc R . .
C8 C 0.9225(14) 0.6953(3) 0.2215(13) 0.149(4) Uani 1 1 d . . .
H8A H 0.9729 0.6930 0.1284 0.223 Uiso 1 1 calc R . .
H8B H 0.8661 0.6627 0.2428 0.223 Uiso 1 1 calc R . .
H8C H 1.0180 0.7030 0.2967 0.223 Uiso 1 1 calc R . .
C9 C 0.6359(9) 0.9540(3) 0.0761(9) 0.112(2) Uani 1 1 d . . .
H9 H 0.5418 0.9784 0.0707 0.134 Uiso 1 1 calc R . .
C10 C 0.9360(8) 0.93919(19) 0.0519(7) 0.0805(15) Uani 1 1 d . . .
C11 C 1.1180(8) 0.9631(2) 0.0247(7) 0.0848(15) Uani 1 1 d . . .
H11 H 1.2131 0.9362 0.0354 0.102 Uiso 1 1 calc R . .
C12 C 1.1253(10) 0.9910(2) -0.1248(7) 0.0959(18) Uani 1 1 d . . .
H12A H 1.1776 0.9681 -0.1944 0.115 Uiso 1 1 calc R . .
H12B H 1.0033 1.0007 -0.1644 0.115 Uiso 1 1 calc R . .
C13 C 1.2421(10) 1.0391(2) -0.0986(7) 0.0951(18) Uani 1 1 d . . .
H13A H 1.3662 1.0326 -0.1220 0.114 Uiso 1 1 calc R . .
H13B H 1.1926 1.0682 -0.1571 0.114 Uiso 1 1 calc R . .
C14 C 1.2358(7) 1.04975(19) 0.0618(6) 0.0758(14) Uani 1 1 d . . .
C15 C 1.1670(7) 1.00755(19) 0.1320(6) 0.0710(13) Uani 1 1 d . . .
C16 C 1.1436(8) 1.0101(2) 0.2791(7) 0.0874(17) Uani 1 1 d . . .
H16 H 1.0971 0.9817 0.3272 0.105 Uiso 1 1 calc R . .
C17 C 1.1902(8) 1.0554(3) 0.3540(7) 0.0884(16) Uani 1 1 d . . .
C18 C 1.2628(8) 1.0970(2) 0.2868(8) 0.0918(17) Uani 1 1 d . . .
H18 H 1.2962 1.1268 0.3407 0.110 Uiso 1 1 calc R . .
C19 C 1.2866(8) 1.0950(2) 0.1408(7) 0.0823(15) Uani 1 1 d . . .
H19 H 1.3359 1.1234 0.0943 0.099 Uiso 1 1 calc R . .
C20 C 0.1826(7) 0.3736(2) 0.3240(6) 0.0776(14) Uani 1 1 d . . .
C21 C 0.3127(9) 0.4117(2) 0.3505(7) 0.0899(17) Uani 1 1 d . . .
C22 C 0.4913(9) 0.4016(2) 0.3204(8) 0.0945(18) Uani 1 1 d . . .
H22 H 0.5777 0.4281 0.3338 0.113 Uiso 1 1 calc R . .
C23 C 0.5435(8) 0.3542(2) 0.2720(7) 0.0797(15) Uani 1 1 d . . .
H23 H 0.6649 0.3484 0.2556 0.096 Uiso 1 1 calc R . .
C24 C 0.4155(7) 0.31423(18) 0.2469(6) 0.0694(13) Uani 1 1 d . . .
C25 C 0.2319(7) 0.3248(2) 0.2718(6) 0.0733(13) Uani 1 1 d . . .
C26 C -0.0290(10) 0.3729(3) 0.5009(9) 0.111(2) Uani 1 1 d . . .
H26A H -0.0156 0.3362 0.5198 0.167 Uiso 1 1 calc R . .
H26B H -0.1510 0.3835 0.5166 0.167 Uiso 1 1 calc R . .
H26C H 0.0565 0.3919 0.5660 0.167 Uiso 1 1 calc R . .
C27 C 0.3856(15) 0.4963(3) 0.4499(16) 0.180(5) Uani 1 1 d . . .
H27A H 0.4781 0.4813 0.5179 0.270 Uiso 1 1 calc R . .
H27B H 0.3274 0.5246 0.4963 0.270 Uiso 1 1 calc R . .
H27C H 0.4404 0.5090 0.3654 0.270 Uiso 1 1 calc R . .
C28 C 0.1561(9) 0.2437(3) 0.2001(8) 0.101(2) Uani 1 1 d . . .
H28 H 0.0648 0.2192 0.1761 0.121 Uiso 1 1 calc R . .
C29 C 0.4558(7) 0.2623(2) 0.2061(6) 0.0757(14) Uani 1 1 d . . .
C30 C 0.6509(7) 0.2422(2) 0.2070(6) 0.0800(15) Uani 1 1 d . . .
H30 H 0.7310 0.2705 0.1791 0.096 Uiso 1 1 calc R . .
C31 C 0.7178(9) 0.2219(3) 0.3589(8) 0.1042(19) Uani 1 1 d . . .
H31A H 0.8173 0.2434 0.4012 0.125 Uiso 1 1 calc R . .
H31B H 0.6196 0.2232 0.4230 0.125 Uiso 1 1 calc R . .
C32 C 0.7824(10) 0.1659(3) 0.3447(8) 0.110(2) Uani 1 1 d . . .
H32A H 0.9119 0.1630 0.3747 0.132 Uiso 1 1 calc R . .
H32B H 0.7160 0.1426 0.4045 0.132 Uiso 1 1 calc R . .
C33 C 0.7441(7) 0.1533(2) 0.1851(7) 0.0799(15) Uani 1 1 d . . .
C34 C 0.6697(7) 0.19540(19) 0.1070(7) 0.0726(13) Uani 1 1 d . . .
C35 C 0.6205(8) 0.1920(2) -0.0417(7) 0.0809(15) Uani 1 1 d . . .
H35 H 0.5683 0.2202 -0.0936 0.097 Uiso 1 1 calc R . .
C36 C 0.6514(8) 0.1452(2) -0.1111(7) 0.0853(15) Uani 1 1 d . . .
C37 C 0.7290(8) 0.1025(2) -0.0358(7) 0.0864(16) Uani 1 1 d . . .
H37 H 0.7478 0.0713 -0.0845 0.104 Uiso 1 1 calc R . .
C38 C 0.7772(8) 0.1071(2) 0.1112(8) 0.0920(17) Uani 1 1 d . . .
H38 H 0.8327 0.0792 0.1625 0.110 Uiso 1 1 calc R . .
Cl1 Cl 0.5893(3) 0.13896(7) -0.2983(2) 0.1245(7) Uani 1 1 d . . .
Cl2 Cl 1.1519(4) 1.05971(10) 0.5396(2) 0.1442(8) Uani 1 1 d . . .
N1 N 0.5912(7) 0.90735(18) 0.1145(6) 0.0909(14) Uani 1 1 d . . .
N2 N 0.8005(7) 0.97249(18) 0.0427(7) 0.1052(17) Uani 1 1 d . . .
N3 N 0.0997(6) 0.28760(18) 0.2462(6) 0.0856(13) Uani 1 1 d . . .
N4 N 0.3267(6) 0.22735(18) 0.1807(6) 0.0923(14) Uani 1 1 d . . .
O1 O 0.5221(6) 0.80620(14) 0.1924(5) 0.0907(11) Uani 1 1 d . . .
O2 O 0.7889(7) 0.73595(16) 0.2161(6) 0.1159(15) Uani 1 1 d . . .
O3 O 0.0047(5) 0.38334(15) 0.3546(5) 0.0911(12) Uani 1 1 d . . .
O4 O 0.2543(7) 0.45770(16) 0.4059(6) 0.1198(16) 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 O1 1.375(7) . ?
C1 C2 1.386(8) . ?
C1 C6 1.396(7) . ?
C2 O2 1.345(7) . ?
C2 C3 1.404(8) . ?
C3 C4 1.368(9) . ?
C4 C5 1.410(8) . ?
C5 C10 1.407(7) . ?
C5 C6 1.429(7) . ?
C6 N1 1.368(7) . ?
C7 O1 1.409(9) . ?
C8 O2 1.429(9) . ?
C9 N1 1.296(8) . ?
C9 N2 1.359(8) . ?
C10 N2 1.309(7) . ?
C10 C11 1.512(8) . ?
C11 C15 1.525(8) . ?
C11 C12 1.548(9) . ?
C12 C13 1.508(9) . ?
C13 C14 1.497(8) . ?
C14 C15 1.375(7) . ?
C14 C19 1.399(8) . ?
C15 C16 1.373(8) . ?
C16 C17 1.375(9) . ?
C17 C18 1.360(9) . ?
C17 Cl2 1.749(6) . ?
C18 C19 1.364(8) . ?
C20 C21 1.373(8) . ?
C20 O3 1.384(7) . ?
C20 C25 1.398(8) . ?
C21 O4 1.365(7) . ?
C21 C22 1.390(9) . ?
C22 C23 1.358(9) . ?
C23 C24 1.396(7) . ?
C24 C25 1.415(7) . ?
C24 C29 1.419(7) . ?
C25 N3 1.366(7) . ?
C26 O3 1.408(8) . ?
C27 O4 1.414(10) . ?
C28 N3 1.282(8) . ?
C28 N4 1.349(8) . ?
C29 N4 1.311(7) . ?
C29 C30 1.523(8) . ?
C30 C34 1.521(8) . ?
C30 C31 1.525(9) . ?
C31 C32 1.518(10) . ?
C32 C33 1.498(9) . ?
C33 C34 1.380(8) . ?
C33 C38 1.392(9) . ?
C34 C35 1.379(8) . ?
C35 C36 1.383(8) . ?
C36 C37 1.388(8) . ?
C36 Cl1 1.740(6) . ?
C37 C38 1.365(9) . ?

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
O1 C1 C2 119.8(5) . . ?
O1 C1 C6 120.3(5) . . ?
C2 C1 C6 119.9(5) . . ?
O2 C2 C1 115.8(6) . . ?
O2 C2 C3 124.1(5) . . ?
C1 C2 C3 120.0(5) . . ?
C4 C3 C2 121.1(6) . . ?
C3 C4 C5 120.3(6) . . ?
C10 C5 C4 124.7(5) . . ?
C10 C5 C6 116.6(5) . . ?
C4 C5 C6 118.6(5) . . ?
N1 C6 C1 118.6(5) . . ?
N1 C6 C5 121.2(5) . . ?
C1 C6 C5 120.1(5) . . ?
N1 C9 N2 129.3(6) . . ?
N2 C10 C5 121.5(5) . . ?
N2 C10 C11 113.9(5) . . ?
C5 C10 C11 124.6(5) . . ?
C10 C11 C15 111.0(5) . . ?
C10 C11 C12 115.6(5) . . ?
C15 C11 C12 101.5(4) . . ?
C13 C12 C11 107.4(5) . . ?
C14 C13 C12 103.8(5) . . ?
C15 C14 C19 120.2(5) . . ?
C15 C14 C13 111.0(5) . . ?
C19 C14 C13 128.8(5) . . ?
C16 C15 C14 120.2(5) . . ?
C16 C15 C11 128.6(5) . . ?
C14 C15 C11 111.2(5) . . ?
C15 C16 C17 118.8(5) . . ?
C18 C17 C16 121.7(6) . . ?
C18 C17 Cl2 119.5(5) . . ?
C16 C17 Cl2 118.8(5) . . ?
C17 C18 C19 120.2(6) . . ?
C18 C19 C14 119.0(5) . . ?
C21 C20 O3 119.5(5) . . ?
C21 C20 C25 119.9(5) . . ?
O3 C20 C25 120.5(5) . . ?
O4 C21 C20 116.2(6) . . ?
O4 C21 C22 124.6(6) . . ?
C20 C21 C22 119.2(5) . . ?
C23 C22 C21 122.0(5) . . ?
C22 C23 C24 120.2(6) . . ?
C23 C24 C25 118.2(5) . . ?
C23 C24 C29 125.3(5) . . ?
C25 C24 C29 116.4(4) . . ?
N3 C25 C20 118.6(5) . . ?
N3 C25 C24 121.0(5) . . ?
C20 C25 C24 120.4(5) . . ?
N3 C28 N4 130.3(5) . . ?
N4 C29 C24 121.4(5) . . ?
N4 C29 C30 116.0(5) . . ?
C24 C29 C30 122.2(4) . . ?
C34 C30 C29 113.4(4) . . ?
C34 C30 C31 103.9(5) . . ?
C29 C30 C31 110.4(5) . . ?
C32 C31 C30 108.8(5) . . ?
C33 C32 C31 104.7(6) . . ?
C34 C33 C38 119.3(6) . . ?
C34 C33 C32 111.5(6) . . ?
C38 C33 C32 129.1(6) . . ?
C35 C34 C33 121.2(5) . . ?
C35 C34 C30 127.8(5) . . ?
C33 C34 C30 111.0(5) . . ?
C34 C35 C36 118.0(5) . . ?
C35 C36 C37 122.1(6) . . ?
C35 C36 Cl1 119.5(5) . . ?
C37 C36 Cl1 118.5(5) . . ?
C38 C37 C36 118.7(5) . . ?
C37 C38 C33 120.7(6) . . ?
C9 N1 C6 114.7(5) . . ?
C10 N2 C9 116.6(5) . . ?
C28 N3 C25 114.9(5) . . ?
C29 N4 C28 115.6(5) . . ?
C1 O1 C7 113.5(5) . . ?
C2 O2 C8 119.2(6) . . ?
C20 O3 C26 114.0(5) . . ?
C21 O4 C27 118.5(6) . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        54.35
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.043
_database_code_depnum_ccdc_archive 'CCDC 990952'
