# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_chem_veerendraak_b2_35_3j_0ma
_database_code_depnum_ccdc_archive 'CCDC 1018656'

_audit_update_record             
;
2014-08-09 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H15 Cl N2 O'
_chemical_formula_sum            'C22 H16 Cl N2 O'
_chemical_formula_weight         359.82

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'
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   P12(1)/c1

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

_cell_length_a                   13.5275(10)
_cell_length_b                   7.5746(5)
_cell_length_c                   18.3908(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.098(2)
_cell_angle_gamma                90.00
_cell_volume                     1758.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10366
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         24.08
_reflns_number_total             2764
_reflns_number_gt                2007
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0606P)²+0.2123P] 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       0.0069(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2764
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.003

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 0.63815(5) 1.09980(10) 0.07479(4) 0.0916(3) Uani 1 1 d . . .
O1 O 1.01474(12) 0.7809(2) 0.50674(9) 0.0829(5) Uani 1 1 d . . .
N1 N 1.06200(12) 0.9002(2) 0.41164(10) 0.0582(5) Uani 1 1 d . . .
N2 N 1.13079(14) 1.0622(2) 0.33824(11) 0.0698(5) Uani 1 1 d . . .
C1 C 0.75624(17) 1.0634(3) 0.15232(13) 0.0669(6) Uani 1 1 d . . .
C2 C 0.84374(18) 1.0061(3) 0.13800(13) 0.0693(6) Uani 1 1 d . . .
H2 H 0.8403 0.9878 0.0871 0.083 Uiso 1 1 calc R . .
C3 C 0.93680(17) 0.9759(3) 0.19978(12) 0.0632(6) Uani 1 1 d . . .
H3 H 0.9959 0.9355 0.1903 0.076 Uiso 1 1 calc R . .
C4 C 0.94363(15) 1.0047(3) 0.27549(12) 0.0582(5) Uani 1 1 d . . .
C5 C 1.04552(16) 0.9853(3) 0.34003(12) 0.0607(6) Uani 1 1 d . . .
C6 C 0.99220(16) 0.8003(3) 0.43706(13) 0.0633(6) Uani 1 1 d . . .
C7 C 0.89923(15) 0.7206(3) 0.37825(12) 0.0592(5) Uani 1 1 d . . .
H7 H 0.8967 0.7078 0.3273 0.071 Uiso 1 1 calc R . .
C8 C 0.81847(16) 0.6663(3) 0.39732(12) 0.0622(6) Uani 1 1 d . . .
H8 H 0.8253 0.6829 0.4490 0.075 Uiso 1 1 calc R . .
C9 C 0.72084(15) 0.5843(3) 0.34723(12) 0.0601(6) Uani 1 1 d . . .
C10 C 0.69801(17) 0.5522(3) 0.26853(13) 0.0724(7) Uani 1 1 d . . .
H10 H 0.7463 0.5861 0.2458 0.087 Uiso 1 1 calc R . .
C11 C 0.60536(19) 0.4712(4) 0.22384(15) 0.0826(7) Uani 1 1 d . . .
H11 H 0.5916 0.4512 0.1712 0.099 Uiso 1 1 calc R . .
C12 C 0.53288(19) 0.4195(3) 0.25570(18) 0.0824(8) Uani 1 1 d . . .
H12 H 0.4706 0.3632 0.2253 0.099 Uiso 1 1 calc R . .
C13 C 0.85421(17) 1.0651(3) 0.28828(13) 0.0712(7) Uani 1 1 d . . .
H13 H 0.8577 1.0868 0.3389 0.085 Uiso 1 1 calc R . .
C14 C 0.76068(18) 1.0932(3) 0.22700(14) 0.0742(7) Uani 1 1 d . . .
H14 H 0.7009 1.1320 0.2361 0.089 Uiso 1 1 calc R . .
C15 C 1.20778(16) 1.0347(3) 0.41162(14) 0.0674(6) Uani 1 1 d . . .
C16 C 1.16770(15) 0.9351(3) 0.45806(13) 0.0620(6) Uani 1 1 d . . .
C17 C 0.64533(19) 0.5336(3) 0.37795(15) 0.0775(7) Uani 1 1 d . . .
H17 H 0.6574 0.5553 0.4302 0.093 Uiso 1 1 calc R . .
C18 C 0.55304(19) 0.4516(4) 0.33249(17) 0.0878(8) Uani 1 1 d . . .
H18 H 0.5039 0.4178 0.3545 0.105 Uiso 1 1 calc R . .
C19 C 1.22993(17) 0.8863(3) 0.53307(14) 0.0744(7) Uani 1 1 d . . .
H19 H 1.2037 0.8158 0.5634 0.089 Uiso 1 1 calc R . .
C20 C 1.3335(2) 0.9477(4) 0.56081(16) 0.0871(8) Uani 1 1 d . . .
H20 H 1.3778 0.9172 0.6109 0.105 Uiso 1 1 calc R . .
C21 C 1.3727(2) 1.0535(4) 0.51583(18) 0.0912(9) Uani 1 1 d . . .
H21 H 1.4418 1.0955 0.5371 0.109 Uiso 1 1 calc R . .
C22 C 1.31172(18) 1.0974(3) 0.44079(16) 0.0823(8) Uani 1 1 d . . .
H22 H 1.3386 1.1664 0.4104 0.099 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 C1 1.738(2) . ?
O1 C6 1.215(2) . ?
N1 C16 1.402(2) . ?
N1 C5 1.410(3) . ?
N1 C6 1.415(3) . ?
N2 C5 1.303(3) . ?
N2 C15 1.392(3) . ?
C1 C14 1.371(3) . ?
C1 C2 1.372(3) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C13 1.390(3) . ?
C4 C5 1.467(3) . ?
C6 C7 1.462(3) . ?
C7 C8 1.327(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.450(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(3) . ?
C9 C17 1.388(3) . ?
C10 C11 1.371(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.368(3) . ?
C11 H11 0.9300 . ?
C12 C18 1.360(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.388(3) . ?
C15 C22 1.395(3) . ?
C16 C19 1.383(3) . ?
C17 C18 1.375(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.387(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.387(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.370(4) . ?
C21 H21 0.9300 . ?
C22 H22 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
C16 N1 C5 105.44(17) . . ?
C16 N1 C6 123.75(18) . . ?
C5 N1 C6 130.80(17) . . ?
C5 N2 C15 105.59(18) . . ?
C14 C1 C2 120.9(2) . . ?
C14 C1 Cl1 119.44(18) . . ?
C2 C1 Cl1 119.62(18) . . ?
C1 C2 C3 119.3(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C13 118.5(2) . . ?
C3 C4 C5 120.20(18) . . ?
C13 C4 C5 121.15(19) . . ?
N2 C5 N1 112.60(18) . . ?
N2 C5 C4 121.1(2) . . ?
N1 C5 C4 126.02(18) . . ?
O1 C6 N1 118.00(19) . . ?
O1 C6 C7 123.6(2) . . ?
N1 C6 C7 118.37(19) . . ?
C8 C7 C6 120.20(19) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 127.79(19) . . ?
C7 C8 H8 116.1 . . ?
C9 C8 H8 116.1 . . ?
C10 C9 C17 117.1(2) . . ?
C10 C9 C8 123.19(19) . . ?
C17 C9 C8 119.7(2) . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C18 C12 C11 119.1(2) . . ?
C18 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C4 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C4 C13 H13 119.6 . . ?
C1 C14 C13 119.4(2) . . ?
C1 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
N2 C15 C16 110.87(18) . . ?
N2 C15 C22 128.4(2) . . ?
C16 C15 C22 120.7(2) . . ?
C19 C16 C15 121.8(2) . . ?
C19 C16 N1 132.7(2) . . ?
C15 C16 N1 105.47(18) . . ?
C18 C17 C9 121.2(2) . . ?
C18 C17 H17 119.4 . . ?
C9 C17 H17 119.4 . . ?
C12 C18 C17 120.7(2) . . ?
C12 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C16 C19 C20 116.6(3) . . ?
C16 C19 H19 121.7 . . ?
C20 C19 H19 121.7 . . ?
C21 C20 C19 121.8(3) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C22 C21 C20 121.3(2) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C15 117.6(3) . . ?
C21 C22 H22 121.2 . . ?
C15 C22 H22 121.2 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        24.08
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.028
_atom_sites_special_details      
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6].
RESPONSE: The crystal was poorly diffracting at higher Bragg angles.
The situation did not improve even after recrystallisation and
fresh data collection.
;
# end Validation Reply Form

