# Electronic Supplementary Material (ESI) for Catalysis Science & Technology
# This journal is © The Royal Society of Chemistry 2013


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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
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#  except for the purpose of generating routine backup copies 
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#  data retrieval see:
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data_kdmm
_database_code_depnum_ccdc_archive 'CCDC 846722'
#TrackingRef '- KDMm cif (1).cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 Cl N4 O3'
_chemical_formula_sum            'C17 H15 Cl N4 O3'
_chemical_formula_weight         358.78
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           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a                   7.129(3)
_cell_length_b                   11.454(5)
_cell_length_c                   19.387(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1583.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    421
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      17.71
_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.518
_exptl_crystal_size_mid          0.316
_exptl_crystal_size_min          0.174
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744.0
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      273(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            7593
_diffrn_reflns_av_R_equivalents  0.1079
_diffrn_reflns_av_sigmaI/netI    0.1306
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2766
_reflns_number_gt                1989
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1824P)^2^+5.1065P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.9(7)
_refine_ls_number_reflns         2766
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1887
_refine_ls_R_factor_gt           0.1524
_refine_ls_wR_factor_ref         0.3845
_refine_ls_wR_factor_gt          0.3606
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_restrained_S_all      1.184
_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 0.837(2) 1.0810(12) 0.7268(7) 0.052(5) Uani 1 1 d . . .
H1 H 0.8192 1.1157 0.6839 0.062 Uiso 1 1 calc R . .
C2 C 0.8673(19) 0.9678(16) 0.7316(5) 0.057(5) Uani 1 1 d . . .
H2 H 0.8559 0.9227 0.6919 0.069 Uiso 1 1 calc R . .
C3 C 0.915(2) 0.9131(11) 0.7917(6) 0.041(3) Uani 1 1 d . . .
H3 H 0.9502 0.8349 0.7922 0.050 Uiso 1 1 calc R . .
C4 C 0.9094(17) 0.9790(11) 0.8527(5) 0.034(3) Uani 1 1 d . . .
C5 C 0.8716(17) 1.1017(9) 0.8451(7) 0.038(3) Uani 1 1 d . . .
H5 H 0.8766 1.1499 0.8836 0.046 Uiso 1 1 calc R . .
C6 C 0.8305(18) 1.1466(10) 0.7853(7) 0.037(3) Uani 1 1 d . . .
H6 H 0.7963 1.2248 0.7825 0.044 Uiso 1 1 calc R . .
C7 C 0.9540(17) 0.8289(8) 0.9441(5) 0.023(3) Uani 1 1 d . . .
C8 C 0.9863(14) 0.8256(8) 1.0140(4) 0.016(2) Uani 1 1 d . . .
C9 C 1.0193(16) 0.9471(8) 1.0266(5) 0.027(3) Uani 1 1 d . . .
C10 C 1.062(2) 1.0028(9) 1.0937(5) 0.039(3) Uani 1 1 d . . .
H10A H 1.1827 0.9776 1.1094 0.059 Uiso 1 1 calc R . .
H10B H 0.9680 0.9807 1.1268 0.059 Uiso 1 1 calc R . .
H10C H 1.0615 1.0861 1.0883 0.059 Uiso 1 1 calc R . .
C11 C 0.9694(15) 0.7431(8) 1.0640(5) 0.017(2) Uani 1 1 d . . .
H11 H 0.9711 0.7783 1.1073 0.020 Uiso 1 1 calc R . .
C12 C 0.9500(16) 0.6204(8) 1.0714(5) 0.023(3) Uani 1 1 d . . .
C13 C 0.9839(15) 0.5385(7) 1.0166(6) 0.026(3) Uani 1 1 d . . .
C14 C 1.032(2) 0.3373(9) 0.9807(6) 0.045(4) Uani 1 1 d . . .
H14A H 0.9214 0.3113 0.9567 0.067 Uiso 1 1 calc R . .
H14B H 1.0931 0.2715 1.0014 0.067 Uiso 1 1 calc R . .
H14C H 1.1153 0.3745 0.9487 0.067 Uiso 1 1 calc R . .
C15 C 0.9234(17) 0.3755(9) 1.0968(6) 0.030(3) Uani 1 1 d . . .
C16 C 0.847(2) 0.4111(10) 1.2186(5) 0.033(3) Uani 1 1 d . . .
H16A H 0.9503 0.4244 1.2492 0.049 Uiso 1 1 calc R . .
H16B H 0.8237 0.3288 1.2148 0.049 Uiso 1 1 calc R . .
H16C H 0.7367 0.4490 1.2365 0.049 Uiso 1 1 calc R . .
C17 C 0.911(2) 0.5814(11) 1.1429(7) 0.042(5) Uani 1.00(4) 1 d . . .
N1 N 0.9555(14) 0.9317(6) 0.9192(4) 0.025(2) Uani 1 1 d . . .
N2 N 0.9993(14) 1.0055(8) 0.9721(5) 0.032(2) Uani 1 1 d . . .
N3 N 0.9773(12) 0.4211(7) 1.0348(4) 0.022(2) Uani 1 1 d . . .
N4 N 0.8918(13) 0.4600(7) 1.1486(5) 0.025(2) Uani 1 1 d . . .
Cl1 Cl 0.9044(13) 0.7356(6) 0.9037(4) 0.142(3) Uani 1 1 d . . .
O1 O 1.0357(11) 0.5631(6) 0.9589(3) 0.0262(19) Uani 1 1 d . . .
O2 O 0.9100(15) 0.2760(6) 1.1086(5) 0.046(3) Uani 1 1 d . . .
O3 O 0.8833(13) 0.6420(6) 1.1905(3) 0.034(2) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.061(10) 0.041(8) 0.053(9) 0.059(8) -0.020(8) -0.009(7)
C2 0.035(8) 0.135(15) 0.002(5) 0.025(7) -0.002(5) -0.017(9)
C3 0.042(9) 0.042(7) 0.039(7) 0.002(6) 0.010(6) 0.017(7)
C4 0.022(7) 0.057(8) 0.022(6) 0.010(5) 0.004(5) 0.011(6)
C5 0.034(8) 0.014(5) 0.066(8) 0.023(6) -0.002(7) -0.019(5)
C6 0.034(8) 0.021(6) 0.055(8) 0.027(6) -0.006(6) -0.023(5)
C7 0.041(7) 0.011(5) 0.018(4) -0.001(4) 0.018(5) 0.015(5)
C8 0.020(6) 0.014(4) 0.015(4) -0.007(4) 0.008(4) 0.003(4)
C9 0.031(7) 0.015(5) 0.037(6) 0.007(4) -0.029(5) -0.021(5)
C10 0.072(10) 0.018(5) 0.027(6) 0.016(4) 0.006(6) 0.015(6)
C11 0.013(6) 0.021(5) 0.016(4) -0.020(4) 0.014(4) -0.002(4)
C12 0.030(7) 0.007(4) 0.031(6) -0.007(4) 0.007(5) -0.004(5)
C13 0.022(7) 0.004(4) 0.053(7) 0.000(4) 0.017(6) 0.015(4)
C14 0.068(10) 0.013(5) 0.054(7) -0.026(5) -0.010(7) 0.016(6)
C15 0.017(7) 0.026(6) 0.046(7) 0.003(5) -0.005(6) 0.008(5)
C16 0.061(9) 0.037(6) 0.000(4) 0.001(4) 0.008(5) -0.014(6)
C17 0.041(9) 0.039(8) 0.047(8) 0.002(6) 0.018(7) 0.011(6)
N1 0.039(6) 0.002(4) 0.033(5) -0.009(3) 0.010(5) -0.010(4)
N2 0.028(6) 0.033(5) 0.036(5) -0.004(4) 0.004(5) 0.010(4)
N3 0.025(5) 0.011(4) 0.031(5) -0.009(3) -0.002(4) 0.011(4)
N4 0.023(5) 0.012(4) 0.041(5) 0.010(4) 0.000(5) 0.002(4)
Cl1 0.163(7) 0.132(6) 0.133(6) 0.009(5) -0.007(6) -0.010(5)
O1 0.047(5) 0.019(3) 0.012(3) -0.009(3) 0.010(4) -0.001(4)
O2 0.068(7) 0.012(4) 0.058(5) 0.014(4) -0.005(5) -0.008(4)
O3 0.068(6) 0.016(4) 0.016(4) -0.004(3) 0.030(4) -0.007(4)
_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 1.32(2) . ?
C1 C6 1.362(18) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(16) . ?
C3 H3 0.9300 . ?
C4 N1 1.437(13) . ?
C4 C5 1.439(16) . ?
C5 C6 1.301(16) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.272(12) . ?
C7 Cl1 1.371(12) . ?
C7 C8 1.376(14) . ?
C8 C11 1.360(13) . ?
C8 C9 1.431(13) . ?
C9 N2 1.259(13) . ?
C9 C10 1.479(15) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.419(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.438(14) . ?
C12 C17 1.483(16) . ?
C13 O1 1.212(13) . ?
C13 N3 1.390(12) . ?
C14 N3 1.474(13) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O2 1.166(12) . ?
C15 N3 1.367(14) . ?
C15 N4 1.411(14) . ?
C16 N4 1.504(12) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O3 1.171(14) . ?
C17 N4 1.402(15) . ?
N1 N2 1.366(12) . ?
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 119.2(10) . . ?
C2 C1 H1 120.5 . . ?
C6 C1 H1 120.3 . . ?
C1 C2 C3 123.5(14) . . ?
C1 C2 H2 118.2 . . ?
C3 C2 H2 118.3 . . ?
C2 C3 C4 117.7(13) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C3 C4 N1 123.2(10) . . ?
C3 C4 C5 116.4(10) . . ?
N1 C4 C5 120.2(10) . . ?
C6 C5 C4 121.3(12) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 121.2(11) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.5 . . ?
N1 C7 Cl1 120.5(9) . . ?
N1 C7 C8 113.3(9) . . ?
Cl1 C7 C8 125.8(9) . . ?
C11 C8 C7 135.0(9) . . ?
C11 C8 C9 124.6(8) . . ?
C7 C8 C9 99.8(8) . . ?
N2 C9 C8 110.8(9) . . ?
N2 C9 C10 122.1(8) . . ?
C8 C9 C10 127.1(9) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.4 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 C12 140.2(9) . . ?
C8 C11 H11 109.9 . . ?
C12 C11 H11 109.9 . . ?
C11 C12 C13 123.8(9) . . ?
C11 C12 C17 114.2(9) . . ?
C13 C12 C17 121.7(9) . . ?
O1 C13 N3 118.0(9) . . ?
O1 C13 C12 125.5(8) . . ?
N3 C13 C12 116.0(9) . . ?
N3 C14 H14A 109.4 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 N3 124.7(11) . . ?
O2 C15 N4 121.2(11) . . ?
N3 C15 N4 114.1(9) . . ?
N4 C16 H16A 109.6 . . ?
N4 C16 H16B 109.4 . . ?
H16A C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 N4 120.7(11) . . ?
O3 C17 C12 126.1(11) . . ?
N4 C17 C12 113.0(10) . . ?
C7 N1 N2 106.9(8) . . ?
C7 N1 C4 133.4(9) . . ?
N2 N1 C4 119.5(8) . . ?
C9 N2 N1 109.1(8) . . ?
C15 N3 C13 127.0(9) . . ?
C15 N3 C14 116.8(9) . . ?
C13 N3 C14 116.1(9) . . ?
C17 N4 C15 127.5(10) . . ?
C17 N4 C16 117.4(9) . . ?
C15 N4 C16 114.9(8) . . ?
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
C6 C1 C2 C3 -8(2) . . . . ?
C1 C2 C3 C4 8(2) . . . . ?
C2 C3 C4 N1 179.7(12) . . . . ?
C2 C3 C4 C5 -6.1(19) . . . . ?
C3 C4 C5 C6 5.2(18) . . . . ?
N1 C4 C5 C6 179.6(12) . . . . ?
C4 C5 C6 C1 -5(2) . . . . ?
C2 C1 C6 C5 6(2) . . . . ?
N1 C7 C8 C11 167.5(12) . . . . ?
Cl1 C7 C8 C11 -6(2) . . . . ?
N1 C7 C8 C9 -3.3(13) . . . . ?
Cl1 C7 C8 C9 -176.5(11) . . . . ?
C11 C8 C9 N2 -169.6(11) . . . . ?
C7 C8 C9 N2 2.5(12) . . . . ?
C11 C8 C9 C10 7.4(19) . . . . ?
C7 C8 C9 C10 179.4(12) . . . . ?
C7 C8 C11 C12 16(2) . . . . ?
C9 C8 C11 C12 -174.7(14) . . . . ?
C8 C11 C12 C13 14(2) . . . . ?
C8 C11 C12 C17 -171.8(14) . . . . ?
C11 C12 C13 O1 2(2) . . . . ?
C17 C12 C13 O1 -171.9(12) . . . . ?
C11 C12 C13 N3 173.5(10) . . . . ?
C17 C12 C13 N3 0.1(17) . . . . ?
C11 C12 C17 O3 5(2) . . . . ?
C13 C12 C17 O3 179.4(13) . . . . ?
C11 C12 C17 N4 179.8(11) . . . . ?
C13 C12 C17 N4 -6.2(18) . . . . ?
Cl1 C7 N1 N2 176.5(10) . . . . ?
C8 C7 N1 N2 2.9(13) . . . . ?
Cl1 C7 N1 C4 1.7(19) . . . . ?
C8 C7 N1 C4 -171.9(11) . . . . ?
C3 C4 N1 C7 -24(2) . . . . ?
C5 C4 N1 C7 161.5(12) . . . . ?
C3 C4 N1 N2 161.3(12) . . . . ?
C5 C4 N1 N2 -12.8(16) . . . . ?
C8 C9 N2 N1 -1.0(13) . . . . ?
C10 C9 N2 N1 -178.1(11) . . . . ?
C7 N1 N2 C9 -1.1(13) . . . . ?
C4 N1 N2 C9 174.5(10) . . . . ?
O2 C15 N3 C13 175.5(13) . . . . ?
N4 C15 N3 C13 -7.3(15) . . . . ?
O2 C15 N3 C14 -3.4(17) . . . . ?
N4 C15 N3 C14 173.8(10) . . . . ?
O1 C13 N3 C15 180.0(11) . . . . ?
C12 C13 N3 C15 7.4(16) . . . . ?
O1 C13 N3 C14 -1.2(16) . . . . ?
C12 C13 N3 C14 -173.7(10) . . . . ?
O3 C17 N4 C15 -178.7(12) . . . . ?
C12 C17 N4 C15 6.6(18) . . . . ?
O3 C17 N4 C16 -3.6(19) . . . . ?
C12 C17 N4 C16 -178.3(11) . . . . ?
O2 C15 N4 C17 176.9(13) . . . . ?
N3 C15 N4 C17 -0.4(17) . . . . ?
O2 C15 N4 C16 1.7(17) . . . . ?
N3 C15 N4 C16 -175.6(10) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.871
_refine_diff_density_rms         0.155