# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2017

####################################################################### 
# 
# 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_klenik1
_database_code_depnum_ccdc_archive 'CCDC 851945'
_audit_update_record             
;
2011-11-02 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;
#TrackingRef 'deposit1.cif.data'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H34 N4 O2'
_chemical_formula_sum            'C32 H34 N4 O2'
_chemical_formula_weight         506.63

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.9834(8)
_cell_length_b                   6.4373(8)
_cell_length_c                   18.610(2)
_cell_angle_alpha                89.153(2)
_cell_angle_beta                 87.364(2)
_cell_angle_gamma                78.992(2)
_cell_volume                     702.85(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    171(2)
_cell_measurement_reflns_used    1168
_cell_measurement_theta_min      3
_cell_measurement_theta_max      23

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             270
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2000)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      171(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  SIEMENS_SMART_CCD
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4303
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_sigmaI/netI    0.1698
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.15
_reflns_number_total             2400
_reflns_number_gt                1103
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'SMART (Siemens, 1995)'
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.02P)²] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2399
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1571
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1179
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_restrained_S_all      0.939
_refine_ls_shift/su_max          0.002
_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
O1 O -0.2937(4) -0.1532(3) 0.39734(11) 0.0434(7) Uani 1 1 d . . .
N1 N 0.9668(5) 0.4123(4) -0.00119(14) 0.0363(8) Uani 1 1 d . . .
N2 N -0.2272(4) 0.0043(4) 0.36686(13) 0.0316(7) Uani 1 1 d . . .
C7 C 0.2310(6) 0.2998(5) 0.18682(17) 0.0334(9) Uani 1 1 d . . .
C4 C 0.4108(5) 0.3358(5) 0.13730(16) 0.0274(8) Uani 1 1 d . . .
C9 C -0.0521(5) 0.2112(5) 0.28970(16) 0.0257(8) Uani 1 1 d . . .
C1 C 0.7747(6) 0.3993(5) 0.04688(16) 0.0317(9) Uani 1 1 d . . .
C10 C -0.1729(5) 0.3373(5) 0.33939(16) 0.0316(9) Uani 1 1 d . . .
H10A H -0.1797 0.4859 0.3400 0.038 Uiso 1 1 calc R . .
C8 C 0.0935(6) 0.2665(5) 0.23315(17) 0.0313(9) Uani 1 1 d . . .
C12 C -0.0737(5) -0.0184(5) 0.30181(16) 0.0242(8) Uani 1 1 d . . .
C11 C -0.2969(5) 0.2242(5) 0.39403(16) 0.0261(8) Uani 1 1 d . . .
C3 C 0.5114(6) 0.1825(5) 0.08826(17) 0.0394(9) Uani 1 1 d . . .
H3A H 0.4541 0.0552 0.0854 0.047 Uiso 1 1 calc R . .
C6 C 0.6750(6) 0.5547(5) 0.09434(17) 0.0395(10) Uani 1 1 d . . .
H6A H 0.7297 0.6836 0.0963 0.047 Uiso 1 1 calc R . .
C16 C 0.1519(5) -0.1602(4) 0.31729(16) 0.0357(9) Uani 1 1 d . . .
H16A H 0.2169 -0.1057 0.3589 0.053 Uiso 1 1 calc R . .
H16B H 0.2571 -0.1625 0.2753 0.053 Uiso 1 1 calc R . .
H16C H 0.1275 -0.3040 0.3278 0.053 Uiso 1 1 calc R . .
C5 C 0.4954(6) 0.5218(5) 0.13885(17) 0.0419(10) Uani 1 1 d . . .
H5A H 0.4271 0.6296 0.1717 0.050 Uiso 1 1 calc R . .
C2 C 0.6942(6) 0.2117(5) 0.04327(17) 0.0387(10) Uani 1 1 d . . .
H2A H 0.7635 0.1045 0.0104 0.046 Uiso 1 1 calc R . .
C13 C -0.2161(6) 0.2428(5) 0.46987(15) 0.0408(10) Uani 1 1 d . . .
H13A H -0.2937 0.1578 0.5032 0.061 Uiso 1 1 calc R . .
H13B H -0.2518 0.3913 0.4848 0.061 Uiso 1 1 calc R . .
H13C H -0.0511 0.1913 0.4703 0.061 Uiso 1 1 calc R . .
C15 C -0.1864(6) -0.1032(5) 0.24003(15) 0.0398(10) Uani 1 1 d . . .
H15A H -0.2060 -0.2480 0.2512 0.060 Uiso 1 1 calc R . .
H15B H -0.0902 -0.1030 0.1960 0.060 Uiso 1 1 calc R . .
H15C H -0.3356 -0.0132 0.2331 0.060 Uiso 1 1 calc R . .
C14 C -0.5549(5) 0.2920(5) 0.39263(17) 0.0399(10) Uani 1 1 d . . .
H14A H -0.6045 0.2726 0.3441 0.060 Uiso 1 1 calc R . .
H14B H -0.5988 0.4415 0.4060 0.060 Uiso 1 1 calc R . .
H14C H -0.6275 0.2056 0.4269 0.060 Uiso 1 1 calc R . .

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
O1 0.0517(17) 0.0266(13) 0.0525(16) 0.0043(12) 0.0150(12) -0.0135(12)
N1 0.0309(18) 0.048(2) 0.0303(16) 0.0096(16) 0.0054(14) -0.0113(16)
N2 0.0357(19) 0.0201(16) 0.0383(18) 0.0008(14) 0.0092(15) -0.0061(14)
C7 0.037(2) 0.032(2) 0.032(2) 0.0048(17) -0.0030(19) -0.0095(18)
C4 0.028(2) 0.031(2) 0.023(2) 0.0025(17) 0.0020(17) -0.0045(17)
C9 0.027(2) 0.0225(19) 0.028(2) 0.0014(16) 0.0015(17) -0.0066(16)
C1 0.034(2) 0.040(2) 0.021(2) -0.0014(17) 0.0019(17) -0.0062(19)
C10 0.034(2) 0.0223(19) 0.040(2) 0.0071(17) -0.0019(18) -0.0076(17)
C8 0.036(2) 0.027(2) 0.031(2) 0.0010(17) -0.0003(19) -0.0071(18)
C12 0.024(2) 0.0213(18) 0.026(2) -0.0011(15) 0.0037(17) -0.0027(16)
C11 0.026(2) 0.0188(18) 0.032(2) -0.0038(15) 0.0042(16) -0.0020(15)
C3 0.042(3) 0.035(2) 0.044(2) 0.0000(19) 0.003(2) -0.0161(19)
C6 0.044(3) 0.036(2) 0.041(2) -0.0062(19) 0.014(2) -0.0175(19)
C16 0.034(2) 0.028(2) 0.044(2) -0.0007(17) -0.0012(17) -0.0034(17)
C5 0.051(3) 0.034(2) 0.041(2) -0.0141(18) 0.016(2) -0.013(2)
C2 0.042(3) 0.038(2) 0.036(2) -0.0068(18) 0.0078(19) -0.0082(19)
C13 0.048(3) 0.037(2) 0.037(2) -0.0024(18) -0.0011(19) -0.0078(19)
C15 0.047(3) 0.035(2) 0.039(2) 0.0016(18) -0.0048(19) -0.0115(19)
C14 0.032(2) 0.038(2) 0.047(2) 0.0033(18) 0.0059(18) -0.0008(18)

_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
O1 N2 1.274(3) . ?
N1 N1 1.269(5) 2_765 ?
N1 C1 1.438(4) . ?
N2 C12 1.477(4) . ?
N2 C11 1.486(4) . ?
C7 C8 1.209(4) . ?
C7 C4 1.434(4) . ?
C4 C3 1.385(4) . ?
C4 C5 1.388(4) . ?
C9 C10 1.332(4) . ?
C9 C8 1.420(4) . ?
C9 C12 1.521(4) . ?
C1 C6 1.373(4) . ?
C1 C2 1.386(4) . ?
C10 C11 1.493(4) . ?
C12 C16 1.515(4) . ?
C12 C15 1.518(4) . ?
C11 C14 1.524(4) . ?
C11 C13 1.526(4) . ?
C3 C2 1.387(4) . ?
C6 C5 1.373(4) . ?

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
N1 N1 C1 113.8(3) 2_765 . ?
O1 N2 C12 122.4(2) . . ?
O1 N2 C11 122.7(2) . . ?
C12 N2 C11 114.9(2) . . ?
C8 C7 C4 174.2(4) . . ?
C3 C4 C5 117.8(3) . . ?
C3 C4 C7 121.0(3) . . ?
C5 C4 C7 121.1(3) . . ?
C10 C9 C8 128.0(3) . . ?
C10 C9 C12 111.6(3) . . ?
C8 C9 C12 120.3(3) . . ?
C6 C1 C2 120.6(3) . . ?
C6 C1 N1 124.7(3) . . ?
C2 C1 N1 114.8(3) . . ?
C9 C10 C11 114.0(3) . . ?
C7 C8 C9 174.6(4) . . ?
N2 C12 C16 110.4(2) . . ?
N2 C12 C15 110.3(3) . . ?
C16 C12 C15 111.2(3) . . ?
N2 C12 C9 99.9(2) . . ?
C16 C12 C9 112.6(3) . . ?
C15 C12 C9 111.9(2) . . ?
N2 C11 C10 99.6(2) . . ?
N2 C11 C14 109.7(3) . . ?
C10 C11 C14 113.0(3) . . ?
N2 C11 C13 111.1(2) . . ?
C10 C11 C13 112.3(3) . . ?
C14 C11 C13 110.6(3) . . ?
C4 C3 C2 121.2(3) . . ?
C5 C6 C1 119.3(3) . . ?
C6 C5 C4 121.9(3) . . ?
C1 C2 C3 119.2(3) . . ?

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
N1 N1 C1 C6 -3.1(5) 2_765 . . . ?
N1 N1 C1 C2 177.8(3) 2_765 . . . ?
C8 C9 C10 C11 -176.2(3) . . . . ?
C12 C9 C10 C11 0.3(4) . . . . ?
O1 N2 C12 C16 -61.2(4) . . . . ?
C11 N2 C12 C16 118.6(3) . . . . ?
O1 N2 C12 C15 62.1(4) . . . . ?
C11 N2 C12 C15 -118.1(3) . . . . ?
O1 N2 C12 C9 -179.9(3) . . . . ?
C11 N2 C12 C9 -0.1(3) . . . . ?
C10 C9 C12 N2 -0.1(3) . . . . ?
C8 C9 C12 N2 176.7(3) . . . . ?
C10 C9 C12 C16 -117.2(3) . . . . ?
C8 C9 C12 C16 59.6(4) . . . . ?
C10 C9 C12 C15 116.7(3) . . . . ?
C8 C9 C12 C15 -66.6(4) . . . . ?
O1 N2 C11 C10 -180.0(3) . . . . ?
C12 N2 C11 C10 0.3(3) . . . . ?
O1 N2 C11 C14 -61.2(4) . . . . ?
C12 N2 C11 C14 119.1(3) . . . . ?
O1 N2 C11 C13 61.4(4) . . . . ?
C12 N2 C11 C13 -118.3(3) . . . . ?
C9 C10 C11 N2 -0.3(3) . . . . ?
C9 C10 C11 C14 -116.7(3) . . . . ?
C9 C10 C11 C13 117.4(3) . . . . ?
C5 C4 C3 C2 1.5(5) . . . . ?
C7 C4 C3 C2 -176.1(3) . . . . ?
C2 C1 C6 C5 0.6(5) . . . . ?
N1 C1 C6 C5 -178.4(3) . . . . ?
C1 C6 C5 C4 -0.1(5) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C7 C4 C5 C6 176.7(3) . . . . ?
C6 C1 C2 C3 0.0(5) . . . . ?
N1 C1 C2 C3 179.1(3) . . . . ?
C4 C3 C2 C1 -1.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.950
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.049


