# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_Probe5
_database_code_depnum_ccdc_archive 'CCDC 1059196'
_audit_update_record             
;
2015-04-13 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        Probe5
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 N6 O'
_chemical_formula_sum            'C21 H20 N6 O'
_chemical_formula_weight         372.43

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5739(12)
_cell_length_b                   8.8346(11)
_cell_length_c                   12.8819(17)
_cell_angle_alpha                85.544(3)
_cell_angle_beta                 78.226(3)
_cell_angle_gamma                80.599(3)
_cell_volume                     941.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4518
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      29.10

_exptl_crystal_description       cube
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             392.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17238
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.616
_diffrn_reflns_theta_max         28.469
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4729
_reflns_number_gt                3464
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4729
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1429
_refine_ls_wR_factor_gt          0.1241
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_restrained_S_all      0.947
_refine_ls_shift/su_max          0.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.13717(15) 0.54773(15) 0.17022(10) 0.0223(3) Uani 1 1 d . . . . .
C2 C 0.26030(16) 0.63437(16) 0.16613(10) 0.0248(3) Uani 1 1 d . . . . .
H2 H 0.3341 0.6458 0.1033 0.030 Uiso 1 1 calc R U . . .
C3 C 0.27147(16) 0.70326(16) 0.25669(10) 0.0254(3) Uani 1 1 d . . . . .
H3 H 0.3544 0.7602 0.2544 0.031 Uiso 1 1 calc R U . . .
C4 C 0.16088(15) 0.68909(14) 0.35144(10) 0.0217(3) Uani 1 1 d . . . . .
C5 C 0.03998(16) 0.60110(16) 0.35371(10) 0.0245(3) Uani 1 1 d . . . . .
H5 H -0.0342 0.5898 0.4164 0.029 Uiso 1 1 calc R U . . .
C6 C 0.02793(16) 0.53005(16) 0.26436(10) 0.0272(3) Uani 1 1 d . . . . .
H6 H -0.0531 0.4706 0.2673 0.033 Uiso 1 1 calc R U . . .
C7 C 0.17168(17) 0.76302(15) 0.45022(10) 0.0251(3) Uani 1 1 d . . . . .
H7A H 0.0663 0.7804 0.4962 0.030 Uiso 1 1 calc R U . . .
H7B H 0.2446 0.6965 0.4885 0.030 Uiso 1 1 calc R U . . .
C8 C 0.25609(15) 0.99115(15) 0.49713(9) 0.0208(3) Uani 1 1 d . . . . .
C9 C 0.33255(15) 1.12210(15) 0.45938(9) 0.0202(3) Uani 1 1 d . . . . .
C10 C 0.37106(14) 1.15677(15) 0.34851(10) 0.0212(3) Uani 1 1 d . . . . .
H10 H 0.3366 1.0921 0.3071 0.025 Uiso 1 1 calc R U . . .
C11 C 0.44999(15) 1.26870(14) 0.29189(9) 0.0209(3) Uani 1 1 d . . . . .
C12 C 0.46620(15) 1.28059(15) 0.17857(10) 0.0224(3) Uani 1 1 d . . . . .
C13 C 0.52544(16) 1.37633(15) 0.33424(10) 0.0246(3) Uani 1 1 d . . . . .
C14 C 0.36221(15) 1.21059(15) 0.53816(10) 0.0224(3) Uani 1 1 d . . . . .
H14 H 0.4139 1.2957 0.5167 0.027 Uiso 1 1 calc R U . . .
C15 C 0.31846(15) 1.17667(15) 0.64418(10) 0.0234(3) Uani 1 1 d . . . . .
H15 H 0.3422 1.2375 0.6929 0.028 Uiso 1 1 calc R U . . .
C16 C 0.23707(15) 1.04938(15) 0.68078(9) 0.0209(3) Uani 1 1 d . . . . .
C17 C 0.21049(15) 0.95567(15) 0.60360(9) 0.0219(3) Uani 1 1 d . . . . .
H17 H 0.1615 0.8690 0.6253 0.026 Uiso 1 1 calc R U . . .
C18 C 0.19330(17) 1.12479(16) 0.86594(10) 0.0262(3) Uani 1 1 d . . . . .
H18A H 0.1023 1.1197 0.9242 0.031 Uiso 1 1 calc R U . . .
H18B H 0.1834 1.2285 0.8346 0.031 Uiso 1 1 calc R U . . .
C19 C 0.34730(19) 1.09120(18) 0.90920(12) 0.0355(4) Uani 1 1 d . . . . .
H19A H 0.3554 0.9905 0.9434 0.053 Uiso 1 1 calc R U . . .
H19B H 0.3461 1.1660 0.9597 0.053 Uiso 1 1 calc R U . . .
H19C H 0.4380 1.0958 0.8520 0.053 Uiso 1 1 calc R U . . .
C20 C 0.10815(17) 0.88434(16) 0.82519(10) 0.0265(3) Uani 1 1 d . . . . .
H20A H 0.1244 0.8558 0.8969 0.032 Uiso 1 1 calc R U . . .
H20B H 0.1581 0.7987 0.7811 0.032 Uiso 1 1 calc R U . . .
C21 C -0.07085(18) 0.91361(19) 0.82525(12) 0.0377(4) Uani 1 1 d . . . . .
H21A H -0.1214 0.9969 0.8700 0.057 Uiso 1 1 calc R U . . .
H21B H -0.1169 0.8228 0.8515 0.057 Uiso 1 1 calc R U . . .
H21C H -0.0877 0.9398 0.7542 0.057 Uiso 1 1 calc R U . . .
N1 N 0.27437(17) 0.49418(16) -0.08866(10) 0.0390(3) Uani 1 1 d . . . . .
N2 N 0.20372(14) 0.49021(14) -0.00472(9) 0.0283(3) Uani 1 1 d . . . . .
N3 N 0.11177(15) 0.47361(14) 0.08212(9) 0.0307(3) Uani 1 1 d . . . . .
N4 N 0.48031(15) 1.29012(14) 0.08801(9) 0.0315(3) Uani 1 1 d . . . . .
N5 N 0.59119(17) 1.46110(15) 0.36514(9) 0.0385(3) Uani 1 1 d . . . . .
O1 O 0.23001(11) 0.90647(10) 0.41990(7) 0.0268(2) Uani 1 1 d . . . . .
N7 N 0.18691(13) 1.01788(13) 0.78605(8) 0.0242(3) 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 C6 1.3881(18) . ?
C1 C2 1.3922(19) . ?
C1 N3 1.4238(16) . ?
C2 C3 1.3840(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.3954(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.3881(18) . ?
C4 C7 1.5005(18) . ?
C5 C6 1.3826(18) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.4350(15) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C17 1.3735(17) . ?
C8 O1 1.3640(15) . ?
C8 C9 1.4265(18) . ?
C9 C14 1.4140(17) . ?
C9 C10 1.4196(17) . ?
C10 C11 1.3685(18) . ?
C10 H10 0.9300 . ?
C11 C13 1.4303(18) . ?
C11 C12 1.4351(17) . ?
C12 N4 1.1458(17) . ?
C13 N5 1.1458(18) . ?
C14 C15 1.3639(17) . ?
C14 H14 0.9300 . ?
C15 C16 1.4189(18) . ?
C15 H15 0.9300 . ?
C16 N7 1.3578(15) . ?
C16 C17 1.4171(17) . ?
C17 H17 0.9300 . ?
C18 N7 1.4647(16) . ?
C18 C19 1.513(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N7 1.4598(17) . ?
C20 C21 1.514(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 N2 1.1274(16) . ?
N2 N3 1.2437(16) . ?

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
C6 C1 C2 120.20(12) . . ?
C6 C1 N3 115.45(12) . . ?
C2 C1 N3 124.35(11) . . ?
C3 C2 C1 119.18(12) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 121.36(12) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 118.35(12) . . ?
C5 C4 C7 119.72(11) . . ?
C3 C4 C7 121.91(12) . . ?
C6 C5 C4 121.11(12) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 119.78(12) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O1 C7 C4 108.34(10) . . ?
O1 C7 H7A 110.0 . . ?
C4 C7 H7A 110.0 . . ?
O1 C7 H7B 110.0 . . ?
C4 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C17 C8 O1 123.06(12) . . ?
C17 C8 C9 121.92(11) . . ?
O1 C8 C9 115.01(10) . . ?
C14 C9 C10 124.58(11) . . ?
C14 C9 C8 115.92(11) . . ?
C10 C9 C8 119.49(11) . . ?
C11 C10 C9 131.29(12) . . ?
C11 C10 H10 114.4 . . ?
C9 C10 H10 114.4 . . ?
C10 C11 C13 126.23(11) . . ?
C10 C11 C12 119.14(11) . . ?
C13 C11 C12 114.60(11) . . ?
N4 C12 C11 179.51(14) . . ?
N5 C13 C11 177.30(15) . . ?
C15 C14 C9 122.94(12) . . ?
C15 C14 H14 118.5 . . ?
C9 C14 H14 118.5 . . ?
C14 C15 C16 120.59(12) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
N7 C16 C17 121.06(11) . . ?
N7 C16 C15 121.27(11) . . ?
C17 C16 C15 117.67(11) . . ?
C8 C17 C16 120.88(12) . . ?
C8 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
N7 C18 C19 113.05(11) . . ?
N7 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
N7 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N7 C20 C21 112.64(11) . . ?
N7 C20 H20A 109.1 . . ?
C21 C20 H20A 109.1 . . ?
N7 C20 H20B 109.1 . . ?
C21 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 N2 N3 170.70(14) . . ?
N2 N3 C1 117.72(11) . . ?
C8 O1 C7 118.63(9) . . ?
C16 N7 C20 121.98(11) . . ?
C16 N7 C18 121.61(11) . . ?
C20 N7 C18 116.10(10) . . ?

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 -0.5(2) . . . . ?
N3 C1 C2 C3 178.95(12) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C2 C3 C4 C5 1.3(2) . . . . ?
C2 C3 C4 C7 179.93(12) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C7 C4 C5 C6 -179.25(12) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
C2 C1 C6 C5 1.2(2) . . . . ?
N3 C1 C6 C5 -178.30(12) . . . . ?
C5 C4 C7 O1 -146.56(12) . . . . ?
C3 C4 C7 O1 34.79(17) . . . . ?
C17 C8 C9 C14 1.60(19) . . . . ?
O1 C8 C9 C14 -179.37(11) . . . . ?
C17 C8 C9 C10 -177.41(12) . . . . ?
O1 C8 C9 C10 1.62(17) . . . . ?
C14 C9 C10 C11 4.7(2) . . . . ?
C8 C9 C10 C11 -176.40(13) . . . . ?
C9 C10 C11 C13 4.7(2) . . . . ?
C9 C10 C11 C12 -177.43(13) . . . . ?
C10 C9 C14 C15 177.66(12) . . . . ?
C8 C9 C14 C15 -1.29(19) . . . . ?
C9 C14 C15 C16 -1.0(2) . . . . ?
C14 C15 C16 N7 -177.27(12) . . . . ?
C14 C15 C16 C17 3.00(19) . . . . ?
O1 C8 C17 C16 -178.55(11) . . . . ?
C9 C8 C17 C16 0.4(2) . . . . ?
N7 C16 C17 C8 177.58(12) . . . . ?
C15 C16 C17 C8 -2.69(19) . . . . ?
C6 C1 N3 N2 177.84(12) . . . . ?
C2 C1 N3 N2 -1.6(2) . . . . ?
C17 C8 O1 C7 -8.40(18) . . . . ?
C9 C8 O1 C7 172.58(11) . . . . ?
C4 C7 O1 C8 -177.23(10) . . . . ?
C17 C16 N7 C20 1.94(19) . . . . ?
C15 C16 N7 C20 -177.78(12) . . . . ?
C17 C16 N7 C18 -171.42(11) . . . . ?
C15 C16 N7 C18 8.86(19) . . . . ?
C21 C20 N7 C16 -83.73(15) . . . . ?
C21 C20 N7 C18 89.98(14) . . . . ?
C19 C18 N7 C16 -92.95(15) . . . . ?
C19 C18 N7 C20 93.31(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C21 H21B N3 0.96 2.69 3.583(2) 155.6 2_566
C19 H19B N4 0.96 2.59 3.4713(19) 152.1 1_556
C19 H19A N4 0.96 2.66 3.451(2) 140.0 2_676
C19 H19A N4 0.96 2.66 3.451(2) 140.0 2_676
C19 H19B N4 0.96 2.59 3.4713(19) 152.1 1_556
C21 H21B N3 0.96 2.69 3.583(2) 155.6 2_566
C19 H19A N4 0.96 2.66 3.451(2) 140.0 2_676
C19 H19B N4 0.96 2.59 3.4713(19) 152.1 1_556
C21 H21B N3 0.96 2.69 3.583(2) 155.6 2_566
C19 H19A N4 0.96 2.66 3.451(2) 140.0 2_676
C19 H19B N4 0.96 2.59 3.4713(19) 152.1 1_556
C21 H21B N3 0.96 2.69 3.583(2) 155.6 2_566

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
