# Electronic Supplementary Material (ESI) for Chemical Science
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 922344'
#TrackingRef 'web_deposit_cif_file_0_JosefinaPerles_1359471416.datos_m.cif'
_chemical_name_systematic        ?
_chemical_name_common            DPAP
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20.50 H13 Cl N3'
_chemical_formula_iupac          ?
_chemical_formula_weight         336.79
_chemical_melting_point          ?
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   8.1851(4)
_cell_length_b                   8.5344(5)
_cell_length_c                   13.5521(9)
_cell_angle_alpha                94.129(5)
_cell_angle_beta                 99.175(4)
_cell_angle_gamma                114.976(4)
_cell_volume                     836.84(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    100.(2)
_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    2.058
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_T_max  0.85
_exptl_special_details           
;
;
_diffrn_ambient_temperature      100.(2)
_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9154
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         67.37
_diffrn_reflns_theta_full        67.37
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.948
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_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.
;
_reflns_number_total             2854
_reflns_number_gt                2520
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_gt          0.1614
_refine_ls_wR_factor_ref         0.1682
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_number_reflns         2854
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0847P)^2^+1.0465P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.646
_refine_diff_density_min         -1.028
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_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  ?
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1673(3) 0.1868(3) 0.38509(18) 0.0222(5) Uani d . 1 . .
C C2 0.1705(3) 0.3522(3) 0.40424(18) 0.0214(5) Uani d . 1 . .
C C3 0.2505(3) 0.4524(3) 0.49982(18) 0.0213(5) Uani d . 1 . .
C C4 0.3288(3) 0.3911(3) 0.57858(18) 0.0224(5) Uani d . 1 . .
C C5 0.3221(4) 0.2256(3) 0.55896(19) 0.0254(6) Uani d . 1 . .
C C6 0.2429(4) 0.1249(3) 0.46482(19) 0.0255(6) Uani d . 1 . .
C C7 0.2541(3) 0.6227(3) 0.51838(18) 0.0246(6) Uani d . 1 . .
C C8 0.4164(3) 0.4975(3) 0.67653(19) 0.0260(6) Uani d . 1 . .
C C9 0.1278(3) -0.0620(3) 0.26508(17) 0.0230(5) Uani d . 1 . .
C C10 0.3041(4) -0.0405(4) 0.26098(19) 0.0271(6) Uani d . 1 . .
C C11 0.3309(4) -0.1862(4) 0.2317(2) 0.0323(6) Uani d . 1 . .
C C12 0.1837(5) -0.3508(4) 0.2077(2) 0.0345(7) Uani d . 1 . .
C C13 0.0093(5) -0.3716(4) 0.2128(2) 0.0374(7) Uani d . 1 . .
C C14 -0.0203(4) -0.2273(4) 0.2409(2) 0.0300(6) Uani d . 1 . .
C C15 -0.0145(3) 0.1260(3) 0.21065(18) 0.0229(5) Uani d . 1 . .
C C16 0.0428(4) 0.1523(4) 0.11962(19) 0.0276(6) Uani d . 1 . .
C C17 -0.0658(4) 0.1789(4) 0.0395(2) 0.0306(6) Uani d . 1 . .
C C18 -0.2307(4) 0.1799(3) 0.0501(2) 0.0302(6) Uani d . 1 . .
C C19 -0.2860(4) 0.1565(3) 0.1414(2) 0.0285(6) Uani d . 1 . .
C C20 -0.1790(4) 0.1292(3) 0.22210(19) 0.0250(6) Uani d . 1 . .
C C21 0.6106(9) 0.5111(9) 0.0041(5) 0.0463(16) Uani d P 0.5 . .
N N1 0.0941(3) 0.0871(3) 0.29039(15) 0.0235(5) Uani d . 1 . .
N N2 0.2588(3) 0.7583(3) 0.53531(18) 0.0334(6) Uani d . 1 . .
N N3 0.4861(3) 0.5810(3) 0.75489(17) 0.0345(6) Uani d . 1 . .
Cl Cl1 0.59869(12) 0.68944(13) 0.04061(6) 0.0552(3) Uani d . 1 . .
H H2 0.120(4) 0.395(4) 0.354(2) 0.020(7) Uiso d . 1 . .
H H5 0.377(4) 0.189(4) 0.608(2) 0.027(7) Uiso d . 1 . .
H H6 0.239(4) 0.019(4) 0.455(2) 0.030(8) Uiso d . 1 . .
H H10 0.396(5) 0.070(5) 0.278(2) 0.031(8) Uiso d . 1 . .
H H11 0.451(5) -0.175(5) 0.227(3) 0.042(9) Uiso d . 1 . .
H H12 0.200(4) -0.443(5) 0.188(2) 0.035(8) Uiso d . 1 . .
H H13 -0.082(5) -0.477(5) 0.198(2) 0.034(8) Uiso d . 1 . .
H H14 -0.139(5) -0.238(4) 0.242(2) 0.031(8) Uiso d . 1 . .
H H16 0.155(5) 0.155(4) 0.113(2) 0.036(8) Uiso d . 1 . .
H H17 -0.023(4) 0.200(4) -0.022(2) 0.031(8) Uiso d . 1 . .
H H18 -0.301(4) 0.203(4) -0.004(2) 0.027(7) Uiso d . 1 . .
H H19 -0.393(5) 0.158(4) 0.149(2) 0.030(8) Uiso d . 1 . .
H H20 -0.213(4) 0.116(4) 0.281(2) 0.028(7) Uiso d . 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0209(12) 0.0220(12) 0.0221(12) 0.0076(10) 0.0048(9) 0.0042(10)
C2 0.0232(12) 0.0222(12) 0.0202(12) 0.0111(10) 0.0041(9) 0.0064(10)
C3 0.0200(11) 0.0207(12) 0.0231(12) 0.0084(10) 0.0058(9) 0.0043(10)
C4 0.0217(12) 0.0234(12) 0.0197(12) 0.0080(10) 0.0040(9) 0.0028(10)
C5 0.0310(13) 0.0272(13) 0.0202(12) 0.0151(11) 0.0031(10) 0.0079(11)
C6 0.0316(13) 0.0207(12) 0.0252(13) 0.0128(11) 0.0051(10) 0.0043(10)
C7 0.0247(12) 0.0277(14) 0.0205(12) 0.0111(11) 0.0038(9) 0.0031(10)
C8 0.0270(13) 0.0250(13) 0.0255(14) 0.0104(11) 0.0059(10) 0.0068(11)
C9 0.0322(13) 0.0212(12) 0.0160(11) 0.0128(11) 0.0027(9) 0.0033(9)
C10 0.0303(14) 0.0233(13) 0.0251(13) 0.0116(12) 0.0003(10) 0.0016(11)
C11 0.0413(16) 0.0395(16) 0.0230(13) 0.0261(14) 0.0024(11) 0.0024(11)
C12 0.062(2) 0.0274(14) 0.0230(13) 0.0284(14) 0.0071(12) 0.0030(11)
C13 0.0518(19) 0.0191(14) 0.0315(15) 0.0080(13) 0.0047(13) 0.0029(12)
C14 0.0330(15) 0.0266(14) 0.0260(13) 0.0088(12) 0.0068(11) 0.0046(11)
C15 0.0279(13) 0.0178(11) 0.0202(12) 0.0092(10) 0.0003(10) 0.0013(9)
C16 0.0293(14) 0.0298(13) 0.0251(13) 0.0143(12) 0.0062(10) 0.0038(11)
C17 0.0420(16) 0.0319(14) 0.0202(13) 0.0184(12) 0.0065(11) 0.0055(11)
C18 0.0399(15) 0.0265(13) 0.0238(13) 0.0181(12) -0.0035(11) 0.0020(11)
C19 0.0274(13) 0.0264(13) 0.0310(14) 0.0136(11) 0.0013(11) -0.0002(11)
C20 0.0292(13) 0.0242(13) 0.0204(13) 0.0111(11) 0.0044(10) 0.0020(10)
C21 0.033(3) 0.040(3) 0.058(4) 0.013(3) 0.002(3) -0.003(3)
N1 0.0289(11) 0.0227(10) 0.0182(10) 0.0124(9) 0.0008(8) 0.0010(8)
N2 0.0418(13) 0.0289(12) 0.0324(12) 0.0190(11) 0.0060(10) 0.0034(10)
N3 0.0391(13) 0.0311(12) 0.0259(12) 0.0110(11) 0.0018(10) 0.0006(10)
Cl1 0.0459(5) 0.0642(6) 0.0453(5) 0.0168(4) 0.0029(4) 0.0094(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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.377(3) ?
C1 C2 . 1.405(3) ?
C1 C6 . 1.405(4) ?
C2 C3 . 1.391(3) ?
C2 H2 . 0.92(3) ?
C3 C4 . 1.404(4) ?
C3 C7 . 1.444(4) ?
C4 C5 . 1.394(4) ?
C4 C8 . 1.440(3) ?
C5 C6 . 1.376(4) ?
C5 H5 . 0.89(3) ?
C6 H6 . 0.89(3) ?
C7 N2 . 1.146(4) ?
C8 N3 . 1.147(3) ?
C9 C10 . 1.387(4) ?
C9 C14 . 1.389(4) ?
C9 N1 . 1.440(3) ?
C10 C11 . 1.393(4) ?
C10 H10 . 0.91(3) ?
C11 C12 . 1.382(4) ?
C11 H11 . 0.96(4) ?
C12 C13 . 1.376(5) ?
C12 H12 . 0.88(3) ?
C13 C14 . 1.390(4) ?
C13 H13 . 0.88(4) ?
C14 H14 . 0.94(3) ?
C15 C16 . 1.389(4) ?
C15 C20 . 1.391(4) ?
C15 N1 . 1.436(3) ?
C16 C17 . 1.386(4) ?
C16 H16 . 0.93(3) ?
C17 C18 . 1.383(4) ?
C17 H17 . 0.95(3) ?
C18 C19 . 1.383(4) ?
C18 H18 . 0.94(3) ?
C19 C20 . 1.387(4) ?
C19 H19 . 0.91(3) ?
C20 H20 . 0.88(3) ?
C21 Cl1 . 1.613(7) ?
C21 C21 2_665 1.723(13) ?
C21 Cl1 2_665 1.809(6) ?
Cl1 C21 2_665 1.809(6) ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 121.4(2) ?
N1 C1 C6 . . 120.1(2) ?
C2 C1 C6 . . 118.5(2) ?
C3 C2 C1 . . 120.2(2) ?
C3 C2 H2 . . 119.5(17) ?
C1 C2 H2 . . 120.4(17) ?
C2 C3 C4 . . 121.0(2) ?
C2 C3 C7 . . 119.6(2) ?
C4 C3 C7 . . 119.4(2) ?
C5 C4 C3 . . 118.2(2) ?
C5 C4 C8 . . 120.9(2) ?
C3 C4 C8 . . 120.8(2) ?
C6 C5 C4 . . 121.3(2) ?
C6 C5 H5 . . 120.5(19) ?
C4 C5 H5 . . 118.1(19) ?
C5 C6 C1 . . 120.8(2) ?
C5 C6 H6 . . 119.(2) ?
C1 C6 H6 . . 120.(2) ?
N2 C7 C3 . . 178.5(3) ?
N3 C8 C4 . . 179.4(3) ?
C10 C9 C14 . . 120.3(2) ?
C10 C9 N1 . . 120.6(2) ?
C14 C9 N1 . . 119.0(2) ?
C9 C10 C11 . . 119.3(3) ?
C9 C10 H10 . . 117.(2) ?
C11 C10 H10 . . 124.(2) ?
C12 C11 C10 . . 120.4(3) ?
C12 C11 H11 . . 118.(2) ?
C10 C11 H11 . . 121.(2) ?
C13 C12 C11 . . 120.0(3) ?
C13 C12 H12 . . 120.(2) ?
C11 C12 H12 . . 120.(2) ?
C12 C13 C14 . . 120.3(3) ?
C12 C13 H13 . . 119.(2) ?
C14 C13 H13 . . 121.(2) ?
C9 C14 C13 . . 119.6(3) ?
C9 C14 H14 . . 119.(2) ?
C13 C14 H14 . . 122.(2) ?
C16 C15 C20 . . 120.2(2) ?
C16 C15 N1 . . 118.8(2) ?
C20 C15 N1 . . 120.9(2) ?
C17 C16 C15 . . 119.8(3) ?
C17 C16 H16 . . 120.(2) ?
C15 C16 H16 . . 120.(2) ?
C18 C17 C16 . . 120.2(3) ?
C18 C17 H17 . . 120.9(18) ?
C16 C17 H17 . . 118.9(18) ?
C19 C18 C17 . . 119.9(2) ?
C19 C18 H18 . . 120.7(18) ?
C17 C18 H18 . . 119.3(18) ?
C18 C19 C20 . . 120.5(3) ?
C18 C19 H19 . . 120.4(19) ?
C20 C19 H19 . . 119.1(19) ?
C19 C20 C15 . . 119.4(2) ?
C19 C20 H20 . . 121.(2) ?
C15 C20 H20 . . 119.6(19) ?
Cl1 C21 C21 . 2_665 65.6(4) ?
Cl1 C21 Cl1 . 2_665 119.9(4) ?
C21 C21 Cl1 2_665 2_665 54.3(3) ?
C1 N1 C15 . . 123.1(2) ?
C1 N1 C9 . . 121.0(2) ?
C15 N1 C9 . . 115.92(19) ?
C21 Cl1 C21 . 2_665 60.1(4) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . -178.0(2) ?
C6 C1 C2 C3 . . . . 1.2(4) ?
C1 C2 C3 C4 . . . . 0.0(4) ?
C1 C2 C3 C7 . . . . 179.6(2) ?
C2 C3 C4 C5 . . . . -0.9(4) ?
C7 C3 C4 C5 . . . . 179.4(2) ?
C2 C3 C4 C8 . . . . 178.1(2) ?
C7 C3 C4 C8 . . . . -1.5(4) ?
C3 C4 C5 C6 . . . . 0.7(4) ?
C8 C4 C5 C6 . . . . -178.3(2) ?
C4 C5 C6 C1 . . . . 0.4(4) ?
N1 C1 C6 C5 . . . . 177.8(2) ?
C2 C1 C6 C5 . . . . -1.4(4) ?
C2 C3 C7 N2 . . . . 180.(100) ?
C4 C3 C7 N2 . . . . -2.(11) ?
C5 C4 C8 N3 . . . . -10.(30) ?
C3 C4 C8 N3 . . . . 170.(100) ?
C14 C9 C10 C11 . . . . 0.5(4) ?
N1 C9 C10 C11 . . . . -177.0(2) ?
C9 C10 C11 C12 . . . . -0.5(4) ?
C10 C11 C12 C13 . . . . -0.1(4) ?
C11 C12 C13 C14 . . . . 0.8(4) ?
C10 C9 C14 C13 . . . . 0.2(4) ?
N1 C9 C14 C13 . . . . 177.7(2) ?
C12 C13 C14 C9 . . . . -0.8(4) ?
C20 C15 C16 C17 . . . . -1.1(4) ?
N1 C15 C16 C17 . . . . 175.9(2) ?
C15 C16 C17 C18 . . . . 0.2(4) ?
C16 C17 C18 C19 . . . . 0.9(4) ?
C17 C18 C19 C20 . . . . -1.1(4) ?
C18 C19 C20 C15 . . . . 0.2(4) ?
C16 C15 C20 C19 . . . . 0.9(4) ?
N1 C15 C20 C19 . . . . -176.0(2) ?
C2 C1 N1 C15 . . . . -12.5(4) ?
C6 C1 N1 C15 . . . . 168.4(2) ?
C2 C1 N1 C9 . . . . 165.8(2) ?
C6 C1 N1 C9 . . . . -13.4(4) ?
C16 C15 N1 C1 . . . . 122.6(3) ?
C20 C15 N1 C1 . . . . -60.4(3) ?
C16 C15 N1 C9 . . . . -55.8(3) ?
C20 C15 N1 C9 . . . . 121.2(2) ?
C10 C9 N1 C1 . . . . -65.7(3) ?
C14 C9 N1 C1 . . . . 116.8(3) ?
C10 C9 N1 C15 . . . . 112.7(3) ?
C14 C9 N1 C15 . . . . -64.8(3) ?
Cl1 C21 Cl1 C21 2_665 . . 2_665 0 ?