# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_cdp297_0m
_database_code_depnum_ccdc_archive 'CCDC 1493290'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2017-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H22 N2'
_chemical_formula_weight         302.41

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   7.9533(6)
_cell_length_b                   9.1569(7)
_cell_length_c                   11.6700(8)
_cell_angle_alpha                83.471(4)
_cell_angle_beta                 82.104(4)
_cell_angle_gamma                88.025(4)
_cell_volume                     836.23(11)
_cell_formula_units_Z            2
_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          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9861
_exptl_absorpt_correction_T_max  0.9916
_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17049
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         30.39
_reflns_number_total             4865
_reflns_number_gt                2855
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1048P)²+0.0659P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4865
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1981
_refine_ls_wR_factor_gt          0.1701
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.006
_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 0.7155(3) 0.3676(2) -0.19325(16) 0.0695(5) Uani 1 1 d . . .
H1 H 0.6786 0.4423 -0.2455 0.083 Uiso 1 1 calc R . .
C2 C 0.6071(2) 0.30905(18) -0.09597(14) 0.0539(4) Uani 1 1 d . . .
C3 C 0.6615(2) 0.19633(16) -0.01456(13) 0.0496(4) Uani 1 1 d . . .
C4 C 0.8279(2) 0.1427(2) -0.03503(15) 0.0613(5) Uani 1 1 d . . .
H4 H 0.8672 0.0682 0.0162 0.074 Uiso 1 1 calc R . .
C5 C 0.9335(3) 0.2008(2) -0.13169(18) 0.0764(6) Uani 1 1 d . . .
H5 H 1.0444 0.1649 -0.1450 0.092 Uiso 1 1 calc R . .
C6 C 0.8779(3) 0.3117(2) -0.20954(18) 0.0798(6) Uani 1 1 d . . .
H6 H 0.9523 0.3489 -0.2740 0.096 Uiso 1 1 calc R . .
C7 C 0.3880(2) 0.25222(17) 0.04348(14) 0.0531(4) Uani 1 1 d . . .
C8 C 0.5211(2) 0.16298(16) 0.07315(13) 0.0480(4) Uani 1 1 d . . .
C9 C 0.5188(2) 0.05062(17) 0.17833(14) 0.0518(4) Uani 1 1 d . . .
H9A H 0.4280 -0.0173 0.1780 0.062 Uiso 1 1 calc R . .
H9B H 0.6250 -0.0052 0.1717 0.062 Uiso 1 1 calc R . .
C10 C 0.49502(18) 0.11341(16) 0.29246(13) 0.0448(4) Uani 1 1 d . . .
C11 C 0.35626(19) 0.10008(17) 0.37660(14) 0.0509(4) Uani 1 1 d . . .
C12 C 0.5362(2) 0.24309(17) 0.44221(14) 0.0516(4) Uani 1 1 d . . .
C13 C 0.6185(3) 0.3307(2) 0.50629(17) 0.0680(5) Uani 1 1 d . . .
H13 H 0.5663 0.3574 0.5773 0.082 Uiso 1 1 calc R . .
C14 C 0.7784(3) 0.3762(2) 0.4616(2) 0.0739(6) Uani 1 1 d . . .
H14 H 0.8353 0.4349 0.5031 0.089 Uiso 1 1 calc R . .
C15 C 0.8582(2) 0.3368(2) 0.35555(19) 0.0675(5) Uani 1 1 d . . .
H15 H 0.9677 0.3682 0.3279 0.081 Uiso 1 1 calc R . .
C16 C 0.7761(2) 0.25103(18) 0.29063(15) 0.0544(4) Uani 1 1 d . . .
H16 H 0.8294 0.2257 0.2194 0.065 Uiso 1 1 calc R . .
C17 C 0.61320(19) 0.20359(15) 0.33336(13) 0.0447(4) Uani 1 1 d . . .
C18 C 0.3378(3) 0.4507(2) -0.11984(19) 0.0774(6) Uani 1 1 d . . .
H18A H 0.4072 0.5320 -0.1547 0.116 Uiso 1 1 calc R . .
H18B H 0.2473 0.4848 -0.0655 0.116 Uiso 1 1 calc R . .
H18C H 0.2910 0.4075 -0.1794 0.116 Uiso 1 1 calc R . .
C19 C 0.2127(2) 0.2614(2) 0.10458(18) 0.0716(5) Uani 1 1 d . . .
H19A H 0.1947 0.1811 0.1651 0.107 Uiso 1 1 calc R . .
H19B H 0.1333 0.2565 0.0502 0.107 Uiso 1 1 calc R . .
H19C H 0.1964 0.3527 0.1381 0.107 Uiso 1 1 calc R . .
C20 C 0.1976(2) 0.0154(2) 0.38260(18) 0.0702(5) Uani 1 1 d . . .
H20A H 0.2058 -0.0405 0.3172 0.105 Uiso 1 1 calc R . .
H20B H 0.1021 0.0823 0.3811 0.105 Uiso 1 1 calc R . .
H20C H 0.1828 -0.0501 0.4534 0.105 Uiso 1 1 calc R . .
C21 C 0.2625(3) 0.1903(2) 0.57267(18) 0.0800(6) Uani 1 1 d . . .
H21A H 0.1500 0.2109 0.5532 0.120 Uiso 1 1 calc R . .
H21B H 0.2962 0.2678 0.6131 0.120 Uiso 1 1 calc R . .
H21C H 0.2636 0.0987 0.6217 0.120 Uiso 1 1 calc R . .
N1 N 0.4407(2) 0.34135(15) -0.05919(13) 0.0593(4) Uani 1 1 d . . .
N2 N 0.38004(18) 0.18021(16) 0.46672(12) 0.0576(4) 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 1.370(3) . ?
C1 C2 1.394(3) . ?
C1 H1 0.9300 . ?
C2 N1 1.367(2) . ?
C2 C3 1.419(2) . ?
C3 C4 1.395(2) . ?
C3 C8 1.423(2) . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.373(2) . ?
C7 N1 1.393(2) . ?
C7 C19 1.480(3) . ?
C8 C9 1.508(2) . ?
C9 C10 1.496(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.372(2) . ?
C10 C17 1.435(2) . ?
C11 N2 1.386(2) . ?
C11 C20 1.493(2) . ?
C12 N2 1.368(2) . ?
C12 C13 1.392(2) . ?
C12 C17 1.412(2) . ?
C13 C14 1.367(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.390(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(2) . ?
C16 H16 0.9300 . ?
C18 N1 1.454(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N2 1.454(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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 117.92(18) . . ?
C6 C1 H1 121.0 . . ?
C2 C1 H1 121.0 . . ?
N1 C2 C1 130.58(17) . . ?
N1 C2 C3 107.52(15) . . ?
C1 C2 C3 121.90(17) . . ?
C4 C3 C2 118.08(16) . . ?
C4 C3 C8 134.57(15) . . ?
C2 C3 C8 107.34(14) . . ?
C5 C4 C3 119.50(18) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 121.21(19) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 N1 109.27(15) . . ?
C8 C7 C19 129.06(16) . . ?
N1 C7 C19 121.67(15) . . ?
C7 C8 C3 106.93(14) . . ?
C7 C8 C9 126.56(16) . . ?
C3 C8 C9 126.51(14) . . ?
C10 C9 C8 114.69(13) . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C17 106.68(14) . . ?
C11 C10 C9 127.32(14) . . ?
C17 C10 C9 125.99(14) . . ?
C10 C11 N2 109.65(14) . . ?
C10 C11 C20 130.22(16) . . ?
N2 C11 C20 120.12(15) . . ?
N2 C12 C13 130.37(17) . . ?
N2 C12 C17 108.10(14) . . ?
C13 C12 C17 121.54(16) . . ?
C14 C13 C12 117.97(18) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C13 C14 C15 121.62(17) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 120.68(18) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.12(18) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C12 119.05(15) . . ?
C16 C17 C10 134.10(15) . . ?
C12 C17 C10 106.82(14) . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 C19 H19A 109.5 . . ?
C7 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C7 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11 C20 H20A 109.5 . . ?
C11 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C11 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 N1 C7 108.95(14) . . ?
C2 N1 C18 124.52(16) . . ?
C7 N1 C18 126.53(17) . . ?
C12 N2 C11 108.74(13) . . ?
C12 N2 C21 125.36(16) . . ?
C11 N2 C21 125.84(16) . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        30.39
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_PARAN05_0m
_database_code_depnum_ccdc_archive 'CCDC 1520633'
_audit_update_record             
;
2016-12-04 deposited with the CCDC.
2017-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N2'
_chemical_formula_sum            'C18 H16 N2'
_chemical_formula_weight         260.33

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.1110(8)
_cell_length_b                   10.0955(7)
_cell_length_c                   23.0729(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.385(3)
_cell_angle_gamma                90
_cell_volume                     2816.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5343
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      23.64

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24898
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.203
_diffrn_reflns_theta_max         28.033
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6759
_reflns_number_gt                4307
_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    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1015P)²+0.0696P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6759
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1783
_refine_ls_wR_factor_gt          0.1500
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.023
_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 0.68041(13) 0.34127(16) 0.00018(8) 0.0471(4) Uani 1 1 d . . . . .
H1 H 0.627538 0.351177 -0.030412 0.056 Uiso 1 1 calc R U . . .
C2 C 0.84375(13) 0.32431(15) 0.04840(8) 0.0446(4) Uani 1 1 d . . . . .
H2A H 0.5064(17) 0.744(2) 0.1367(10) 0.091(7) Uiso 1 1 d . . . . .
C3 C 0.95603(14) 0.31913(19) 0.06486(10) 0.0611(5) Uani 1 1 d . . . . .
H3 H 1.009544 0.328776 0.037873 0.073 Uiso 1 1 calc R U . . .
C4 C 0.98409(17) 0.2994(2) 0.12215(11) 0.0753(7) Uani 1 1 d . . . . .
H4 H 1.058555 0.296207 0.134481 0.090 Uiso 1 1 calc R U . . .
H4A H 0.2281(16) 0.430(2) -0.0165(8) 0.067(6) Uiso 1 1 d . . . . .
C5 C 0.9042(2) 0.2835(2) 0.16324(10) 0.0751(6) Uani 1 1 d . . . . .
H5 H 0.926554 0.270465 0.202072 0.090 Uiso 1 1 calc R U . . .
C6 C 0.79206(17) 0.28714(19) 0.14669(8) 0.0595(5) Uani 1 1 d . . . . .
H6 H 0.739129 0.275011 0.173811 0.071 Uiso 1 1 calc R U . . .
C7 C 0.76103(13) 0.30935(15) 0.08852(7) 0.0430(4) Uani 1 1 d . . . . .
C8 C 0.65643(12) 0.32043(15) 0.05643(8) 0.0435(4) Uani 1 1 d . . . . .
C9 C 0.54425(13) 0.31300(17) 0.08074(9) 0.0539(5) Uani 1 1 d . . . . .
H9A H 0.544724 0.241820 0.108994 0.065 Uiso 1 1 calc R U . . .
H9B H 0.490360 0.290397 0.049541 0.065 Uiso 1 1 calc R U . . .
C10 C 0.50734(13) 0.43841(15) 0.10933(7) 0.0423(4) Uani 1 1 d . . . . .
C11 C 0.55050(14) 0.56192(17) 0.10402(8) 0.0499(4) Uani 1 1 d . . . . .
H11 H 0.610970 0.582618 0.082682 0.060 Uiso 1 1 calc R U . . .
C12 C 0.40846(14) 0.58657(17) 0.16064(7) 0.0472(4) Uani 1 1 d . . . . .
C13 C 0.32694(16) 0.6353(2) 0.19526(8) 0.0604(5) Uani 1 1 d . . . . .
H13 H 0.322348 0.724946 0.204051 0.072 Uiso 1 1 calc R U . . .
C14 C 0.25364(16) 0.5450(2) 0.21585(9) 0.0654(5) Uani 1 1 d . . . . .
H14 H 0.197911 0.574315 0.238779 0.078 Uiso 1 1 calc R U . . .
C15 C 0.26130(15) 0.4117(2) 0.20308(8) 0.0602(5) Uani 1 1 d . . . . .
H15 H 0.211183 0.353104 0.218215 0.072 Uiso 1 1 calc R U . . .
C16 C 0.34102(13) 0.36299(18) 0.16857(7) 0.0488(4) Uani 1 1 d . . . . .
H16 H 0.344808 0.272913 0.160488 0.059 Uiso 1 1 calc R U . . .
C17 C 0.41652(13) 0.45199(15) 0.14580(7) 0.0406(4) Uani 1 1 d . . . . .
C18 C 0.84735(18) 0.3568(2) -0.05999(9) 0.0696(6) Uani 1 1 d . . . . .
H18A H 0.907225 0.418908 -0.055378 0.104 Uiso 1 1 calc R U . . .
H18B H 0.795216 0.386899 -0.090085 0.104 Uiso 1 1 calc R U . . .
H18C H 0.875688 0.271708 -0.070325 0.104 Uiso 1 1 calc R U . . .
C19 C 0.25568(14) -0.00082(17) 0.09447(8) 0.0500(4) Uani 1 1 d . . . . .
C20 C 0.21966(15) 0.02203(18) 0.14889(9) 0.0555(5) Uani 1 1 d . . . . .
H20 H 0.146437 0.037919 0.156822 0.067 Uiso 1 1 calc R U . . .
C21 C 0.40186(13) -0.00646(16) 0.16211(7) 0.0442(4) Uani 1 1 d . . . . .
C22 C 0.51046(15) -0.01683(19) 0.18480(8) 0.0567(5) Uani 1 1 d . . . . .
H22 H 0.528446 -0.007125 0.224317 0.068 Uiso 1 1 calc R U . . .
C23 C 0.59099(15) -0.04238(19) 0.14570(9) 0.0591(5) Uani 1 1 d . . . . .
H23 H 0.664664 -0.048789 0.159221 0.071 Uiso 1 1 calc R U . . .
C24 C 0.56361(15) -0.05835(18) 0.08735(8) 0.0545(5) Uani 1 1 d . . . . .
H24 H 0.619342 -0.075704 0.062353 0.065 Uiso 1 1 calc R U . . .
C25 C 0.45529(13) -0.04924(16) 0.06492(7) 0.0454(4) Uani 1 1 d . . . . .
H25 H 0.437961 -0.062444 0.025535 0.054 Uiso 1 1 calc R U . . .
C26 C 0.37266(13) -0.01987(16) 0.10256(7) 0.0435(4) Uani 1 1 d . . . . .
C27 C 0.18935(15) -0.00218(18) 0.03702(8) 0.0558(5) Uani 1 1 d . . . . .
H27A H 0.217416 -0.072264 0.013180 0.067 Uiso 1 1 calc R U . . .
H27B H 0.113156 -0.023420 0.044002 0.067 Uiso 1 1 calc R U . . .
C28 C 0.19128(12) 0.12561(15) 0.00362(7) 0.0429(4) Uani 1 1 d . . . . .
C29 C 0.22812(13) 0.24534(16) 0.02277(8) 0.0468(4) Uani 1 1 d . . . . .
H29 H 0.260122 0.261641 0.059719 0.056 Uiso 1 1 calc R U . . .
C30 C 0.16288(12) 0.28034(16) -0.06876(7) 0.0441(4) Uani 1 1 d . . . . .
C31 C 0.13080(15) 0.3335(2) -0.12251(8) 0.0595(5) Uani 1 1 d . . . . .
H31 H 0.139471 0.423170 -0.130229 0.071 Uiso 1 1 calc R U . . .
C32 C 0.08572(16) 0.2486(2) -0.16393(9) 0.0671(6) Uani 1 1 d . . . . .
H32 H 0.062419 0.281439 -0.200274 0.081 Uiso 1 1 calc R U . . .
C33 C 0.07430(16) 0.1138(2) -0.15240(9) 0.0654(6) Uani 1 1 d . . . . .
H33 H 0.045275 0.058296 -0.181650 0.078 Uiso 1 1 calc R U . . .
C34 C 0.10485(14) 0.06080(18) -0.09890(8) 0.0540(5) Uani 1 1 d . . . . .
H34 H 0.095718 -0.029044 -0.091660 0.065 Uiso 1 1 calc R U . . .
C35 C 0.15000(11) 0.14531(15) -0.05560(7) 0.0405(4) Uani 1 1 d . . . . .
C36 C 0.3009(2) 0.0447(3) 0.25153(9) 0.0838(7) Uani 1 1 d . . . . .
H36A H 0.342055 -0.021705 0.273322 0.126 Uiso 1 1 calc R U . . .
H36B H 0.225167 0.042983 0.261697 0.126 Uiso 1 1 calc R U . . .
H36C H 0.331981 0.130365 0.260311 0.126 Uiso 1 1 calc R U . . .
N1 N 0.79256(11) 0.34579(13) -0.00559(6) 0.0478(4) Uani 1 1 d . . . . .
N2 N 0.49182(13) 0.65168(15) 0.13475(7) 0.0563(4) Uani 1 1 d . . . . .
N3 N 0.30607(13) 0.01828(16) 0.18995(6) 0.0571(4) Uani 1 1 d . . . . .
N4 N 0.21167(12) 0.33976(15) -0.02000(7) 0.0512(4) 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 C8 1.363(2) . ?
C1 N1 1.373(2) . ?
C1 H1 0.9300 . ?
C2 N1 1.376(2) . ?
C2 C3 1.391(2) . ?
C2 C7 1.412(2) . ?
C3 C4 1.360(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.404(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.433(2) . ?
C8 C9 1.502(2) . ?
C9 C10 1.507(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.360(2) . ?
C10 C17 1.430(2) . ?
C11 N2 1.374(2) . ?
C11 H11 0.9300 . ?
C12 N2 1.371(2) . ?
C12 C13 1.396(2) . ?
C12 C17 1.406(2) . ?
C13 C14 1.376(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.406(2) . ?
C16 H16 0.9300 . ?
C18 N1 1.458(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.373(3) . ?
C19 C26 1.431(2) . ?
C19 C27 1.509(3) . ?
C20 N3 1.370(3) . ?
C20 H20 0.9300 . ?
C21 N3 1.382(2) . ?
C21 C22 1.391(2) . ?
C21 C26 1.405(2) . ?
C22 C23 1.391(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.377(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.385(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.395(2) . ?
C25 H25 0.9300 . ?
C27 C28 1.504(2) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.354(2) . ?
C28 C35 1.441(2) . ?
C29 N4 1.378(2) . ?
C29 H29 0.9300 . ?
C30 N4 1.377(2) . ?
C30 C31 1.386(2) . ?
C30 C35 1.407(2) . ?
C31 C32 1.373(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.395(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.376(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.400(2) . ?
C34 H34 0.9300 . ?
C36 N3 1.451(2) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
N2 H2A 0.95(2) . ?
N4 H4A 0.94(2) . ?

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
C8 C1 N1 111.41(15) . . ?
C8 C1 H1 124.3 . . ?
N1 C1 H1 124.3 . . ?
N1 C2 C3 129.35(17) . . ?
N1 C2 C7 108.14(13) . . ?
C3 C2 C7 122.49(17) . . ?
C4 C3 C2 117.06(19) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
C3 C4 C5 122.04(18) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 120.88(19) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 118.28(19) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C6 C7 C2 119.23(15) . . ?
C6 C7 C8 133.74(16) . . ?
C2 C7 C8 107.02(15) . . ?
C1 C8 C7 105.80(15) . . ?
C1 C8 C9 127.71(16) . . ?
C7 C8 C9 126.48(16) . . ?
C8 C9 C10 114.81(13) . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.5 . . ?
C11 C10 C17 106.14(14) . . ?
C11 C10 C9 127.22(15) . . ?
C17 C10 C9 126.59(14) . . ?
C10 C11 N2 110.16(16) . . ?
C10 C11 H11 124.9 . . ?
N2 C11 H11 124.9 . . ?
N2 C12 C13 130.13(17) . . ?
N2 C12 C17 107.08(15) . . ?
C13 C12 C17 122.78(17) . . ?
C14 C13 C12 117.19(18) . . ?
C14 C13 H13 121.4 . . ?
C12 C13 H13 121.4 . . ?
C13 C14 C15 121.23(18) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 121.91(18) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C17 118.79(17) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C16 C17 C12 118.08(15) . . ?
C16 C17 C10 134.30(15) . . ?
C12 C17 C10 107.62(14) . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C26 105.60(16) . . ?
C20 C19 C27 128.57(17) . . ?
C26 C19 C27 125.81(16) . . ?
N3 C20 C19 110.91(16) . . ?
N3 C20 H20 124.5 . . ?
C19 C20 H20 124.5 . . ?
N3 C21 C22 129.80(16) . . ?
N3 C21 C26 107.60(14) . . ?
C22 C21 C26 122.60(15) . . ?
C21 C22 C23 116.97(17) . . ?
C21 C22 H22 121.5 . . ?
C23 C22 H22 121.5 . . ?
C24 C23 C22 121.22(17) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 121.73(16) . . ?
C23 C24 H24 119.1 . . ?
C25 C24 H24 119.1 . . ?
C24 C25 C26 118.68(16) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
C25 C26 C21 118.75(15) . . ?
C25 C26 C19 133.50(16) . . ?
C21 C26 C19 107.74(15) . . ?
C28 C27 C19 114.76(14) . . ?
C28 C27 H27A 108.6 . . ?
C19 C27 H27A 108.6 . . ?
C28 C27 H27B 108.6 . . ?
C19 C27 H27B 108.6 . . ?
H27A C27 H27B 107.6 . . ?
C29 C28 C35 106.00(14) . . ?
C29 C28 C27 127.85(16) . . ?
C35 C28 C27 126.12(14) . . ?
C28 C29 N4 110.66(15) . . ?
C28 C29 H29 124.7 . . ?
N4 C29 H29 124.7 . . ?
N4 C30 C31 130.30(17) . . ?
N4 C30 C35 107.06(15) . . ?
C31 C30 C35 122.64(16) . . ?
C32 C31 C30 117.41(19) . . ?
C32 C31 H31 121.3 . . ?
C30 C31 H31 121.3 . . ?
C31 C32 C33 121.07(19) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 H32 119.5 . . ?
C34 C33 C32 121.74(18) . . ?
C34 C33 H33 119.1 . . ?
C32 C33 H33 119.1 . . ?
C33 C34 C35 118.43(18) . . ?
C33 C34 H34 120.8 . . ?
C35 C34 H34 120.8 . . ?
C34 C35 C30 118.68(16) . . ?
C34 C35 C28 133.75(15) . . ?
C30 C35 C28 107.56(14) . . ?
N3 C36 H36A 109.5 . . ?
N3 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N3 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C1 N1 C2 107.60(14) . . ?
C1 N1 C18 126.08(16) . . ?
C2 N1 C18 126.01(15) . . ?
C12 N2 C11 108.98(15) . . ?
C12 N2 H2A 126.1(14) . . ?
C11 N2 H2A 124.9(14) . . ?
C20 N3 C21 108.15(15) . . ?
C20 N3 C36 126.63(18) . . ?
C21 N3 C36 125.09(17) . . ?
C30 N4 C29 108.71(14) . . ?
C30 N4 H4A 125.0(12) . . ?
C29 N4 H4A 126.2(12) . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.158

