# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_0356_131113_skp_74_1_0m
_database_code_depnum_ccdc_archive 'CCDC 989506'
_audit_update_record             
;
2014-03-02 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H26 N2'
_chemical_formula_sum            'C34 H26 N2'
_chemical_formula_weight         462.57

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.594(5)
_cell_length_b                   9.946(5)
_cell_length_c                   17.135(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 109.110(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2511.1(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7057
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      25.96

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      1.223
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9824
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18214
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4405
_reflns_number_gt                3359
_reflns_threshold_expression     >2σ(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2σ(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)+(0.0750P)²+0.4194P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4405
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1420
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.47828(10) 0.05993(16) 0.68324(10) 0.0555(4) Uani 1 1 d . . .
H1 H 0.4452 -0.0130 0.6475 0.067 Uiso 1 1 calc R . .
C2 C 0.58144(11) 0.04702(17) 0.69275(11) 0.0607(4) Uani 1 1 d . . .
H2 H 0.6170 0.0590 0.7512 0.073 Uiso 1 1 calc R . .
C3 C 0.59758(13) 0.16568(19) 0.64591(14) 0.0776(6) Uani 1 1 d . . .
H3 H 0.6526 0.1822 0.6375 0.093 Uiso 1 1 calc R . .
C4 C 0.52605(12) 0.24466(19) 0.61769(12) 0.0698(5) Uani 1 1 d . . .
H4 H 0.5253 0.3236 0.5884 0.084 Uiso 1 1 calc R . .
C5 C 0.44869(10) 0.19355(16) 0.63796(9) 0.0538(4) Uani 1 1 d . . .
C6 C 0.36562(10) 0.24877(15) 0.62167(9) 0.0510(4) Uani 1 1 d . . .
C7 C 0.34339(11) 0.38669(17) 0.58846(10) 0.0578(4) Uani 1 1 d . . .
C8 C 0.40397(15) 0.49314(19) 0.61542(14) 0.0767(5) Uani 1 1 d . . .
H8 H 0.4590 0.4792 0.6571 0.092 Uiso 1 1 calc R . .
C9 C 0.3828(2) 0.6198(2) 0.58054(19) 0.1052(8) Uani 1 1 d . . .
H9 H 0.4240 0.6899 0.5989 0.126 Uiso 1 1 calc R . .
C10 C 0.3022(2) 0.6429(3) 0.5196(2) 0.1170(10) Uani 1 1 d . . .
H10 H 0.2892 0.7275 0.4956 0.140 Uiso 1 1 calc R . .
C11 C 0.24051(19) 0.5400(3) 0.49385(16) 0.1008(8) Uani 1 1 d . . .
H11 H 0.1850 0.5558 0.4532 0.121 Uiso 1 1 calc R . .
C12 C 0.26043(13) 0.4130(2) 0.52812(11) 0.0717(5) Uani 1 1 d . . .
H12 H 0.2179 0.3444 0.5106 0.086 Uiso 1 1 calc R . .
C13 C 0.29138(10) 0.16890(16) 0.63600(9) 0.0525(4) Uani 1 1 d . . .
C14 C 0.25378(12) 0.20520(18) 0.69542(11) 0.0653(5) Uani 1 1 d . . .
H14 H 0.2724 0.2841 0.7253 0.078 Uiso 1 1 calc R . .
C15 C 0.18852(14) 0.1253(2) 0.71112(14) 0.0818(6) Uani 1 1 d . . .
H15 H 0.1644 0.1501 0.7520 0.098 Uiso 1 1 calc R . .
C16 C 0.15941(14) 0.0098(2) 0.66666(16) 0.0858(7) Uani 1 1 d . . .
H16 H 0.1159 -0.0440 0.6776 0.103 Uiso 1 1 calc R . .
C17 C 0.19443(14) -0.0260(2) 0.60637(15) 0.0840(6) Uani 1 1 d . . .
H17 H 0.1742 -0.1036 0.5756 0.101 Uiso 1 1 calc R . .
C18 C 0.25962(12) 0.05271(18) 0.59111(11) 0.0679(5) Uani 1 1 d . . .
H18 H 0.2829 0.0275 0.5498 0.081 Uiso 1 1 calc R . .
C19 C 0.45961(10) 0.05264(16) 0.76310(10) 0.0556(4) Uani 1 1 d . . .
C20 C 0.40797(13) -0.03983(19) 0.78492(12) 0.0715(5) Uani 1 1 d . . .
H20 H 0.3798 -0.1126 0.7526 0.086 Uiso 1 1 calc R . .
C21 C 0.45272(12) 0.1022(2) 0.89107(11) 0.0680(5) Uani 1 1 d . . .
C22 C 0.48975(10) 0.14499(16) 0.83078(10) 0.0561(4) Uani 1 1 d . . .
C23 C 0.54351(12) 0.26020(19) 0.84633(12) 0.0699(5) Uani 1 1 d . . .
H23 H 0.5682 0.2916 0.8072 0.084 Uiso 1 1 calc R . .
C24 C 0.55965(15) 0.3268(2) 0.91972(13) 0.0838(6) Uani 1 1 d . . .
H24 H 0.5957 0.4035 0.9301 0.101 Uiso 1 1 calc R . .
C25 C 0.52318(15) 0.2821(3) 0.97877(13) 0.0874(6) Uani 1 1 d . . .
H25 H 0.5356 0.3289 1.0282 0.105 Uiso 1 1 calc R . .
C26 C 0.46944(14) 0.1708(3) 0.96553(12) 0.0849(6) Uani 1 1 d . . .
H26 H 0.4446 0.1413 1.0050 0.102 Uiso 1 1 calc R . .
C27 C 0.60563(11) -0.08589(19) 0.66521(10) 0.0624(4) Uani 1 1 d . . .
C28 C 0.61529(16) -0.1157(3) 0.59143(14) 0.0943(7) Uani 1 1 d . . .
H28 H 0.6068 -0.0553 0.5481 0.113 Uiso 1 1 calc R . .
C29 C 0.64568(13) -0.3060(2) 0.66326(17) 0.0851(7) Uani 1 1 d . . .
C30 C 0.66771(17) -0.4359(3) 0.6913(3) 0.1189(11) Uani 1 1 d . . .
H30 H 0.6823 -0.5002 0.6583 0.143 Uiso 1 1 calc R . .
C31 C 0.66748(17) -0.4671(3) 0.7687(3) 0.1273(13) Uani 1 1 d . . .
H31 H 0.6825 -0.5539 0.7888 0.153 Uiso 1 1 calc R . .
C32 C 0.64514(17) -0.3711(3) 0.81824(19) 0.1087(8) Uani 1 1 d . . .
H32 H 0.6453 -0.3948 0.8708 0.130 Uiso 1 1 calc R . .
C33 C 0.62286(14) -0.2418(2) 0.79052(13) 0.0782(5) Uani 1 1 d . . .
H33 H 0.6074 -0.1787 0.8236 0.094 Uiso 1 1 calc R . .
C34 C 0.62380(11) -0.20711(17) 0.71249(11) 0.0620(4) Uani 1 1 d . . .
N1 N 0.40311(11) -0.01092(18) 0.86124(10) 0.0833(5) Uani 1 1 d . . .
H1A H 0.3735 -0.0567 0.8866 0.100 Uiso 1 1 calc R . .
N2 N 0.63919(15) -0.2467(3) 0.58992(15) 0.1128(7) Uani 1 1 d . . .
H2A H 0.6488 -0.2862 0.5489 0.135 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C19 1.491(2) . ?
C1 C5 1.532(2) . ?
C1 C2 1.568(2) . ?
C1 H1 0.9800 . ?
C2 C27 1.493(2) . ?
C2 C3 1.494(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.320(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.452(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.349(2) . ?
C6 C7 1.482(2) . ?
C6 C13 1.489(2) . ?
C7 C12 1.391(2) . ?
C7 C8 1.393(3) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.365(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.379(2) . ?
C13 C18 1.387(2) . ?
C14 C15 1.385(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.353(2) . ?
C19 C22 1.433(2) . ?
C20 N1 1.365(3) . ?
C20 H20 0.9300 . ?
C21 N1 1.366(3) . ?
C21 C26 1.394(3) . ?
C21 C22 1.404(2) . ?
C22 C23 1.393(2) . ?
C23 C24 1.370(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.386(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.362(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.354(3) . ?
C27 C34 1.428(3) . ?
C28 N2 1.358(3) . ?
C28 H28 0.9300 . ?
C29 N2 1.362(3) . ?
C29 C30 1.382(4) . ?
C29 C34 1.408(3) . ?
C30 C31 1.362(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.396(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.375(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.386(3) . ?
C33 H33 0.9300 . ?
N1 H1A 0.8600 . ?
N2 H2A 0.8600 . ?

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
C19 C1 C5 112.96(13) . . ?
C19 C1 C2 113.73(13) . . ?
C5 C1 C2 104.61(12) . . ?
C19 C1 H1 108.4 . . ?
C5 C1 H1 108.4 . . ?
C2 C1 H1 108.4 . . ?
C27 C2 C3 115.16(16) . . ?
C27 C2 C1 113.35(14) . . ?
C3 C2 C1 103.12(13) . . ?
C27 C2 H2 108.3 . . ?
C3 C2 H2 108.3 . . ?
C1 C2 H2 108.3 . . ?
C4 C3 C2 113.33(16) . . ?
C4 C3 H3 123.3 . . ?
C2 C3 H3 123.3 . . ?
C3 C4 C5 111.89(16) . . ?
C3 C4 H4 124.1 . . ?
C5 C4 H4 124.1 . . ?
C6 C5 C4 128.65(15) . . ?
C6 C5 C1 124.57(14) . . ?
C4 C5 C1 106.78(13) . . ?
C5 C6 C7 122.97(14) . . ?
C5 C6 C13 119.62(14) . . ?
C7 C6 C13 117.40(13) . . ?
C12 C7 C8 117.92(17) . . ?
C12 C7 C6 120.20(16) . . ?
C8 C7 C6 121.88(16) . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.5(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C14 C13 C18 117.82(16) . . ?
C14 C13 C6 121.56(15) . . ?
C18 C13 C6 120.59(15) . . ?
C13 C14 C15 120.69(18) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.86(19) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 121.41(19) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
C20 C19 C22 106.22(16) . . ?
C20 C19 C1 126.81(16) . . ?
C22 C19 C1 126.92(14) . . ?
C19 C20 N1 110.25(18) . . ?
C19 C20 H20 124.9 . . ?
N1 C20 H20 124.9 . . ?
N1 C21 C26 131.19(18) . . ?
N1 C21 C22 107.05(17) . . ?
C26 C21 C22 121.76(19) . . ?
C23 C22 C21 118.37(17) . . ?
C23 C22 C19 134.39(16) . . ?
C21 C22 C19 107.23(15) . . ?
C24 C23 C22 119.44(18) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 121.3(2) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C26 C25 C24 121.1(2) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C21 118.1(2) . . ?
C25 C26 H26 121.0 . . ?
C21 C26 H26 121.0 . . ?
C28 C27 C34 106.42(18) . . ?
C28 C27 C2 127.28(19) . . ?
C34 C27 C2 126.29(16) . . ?
C27 C28 N2 110.1(2) . . ?
C27 C28 H28 125.0 . . ?
N2 C28 H28 125.0 . . ?
N2 C29 C30 131.4(3) . . ?
N2 C29 C34 106.9(2) . . ?
C30 C29 C34 121.7(3) . . ?
C31 C30 C29 118.2(3) . . ?
C31 C30 H30 120.9 . . ?
C29 C30 H30 120.9 . . ?
C30 C31 C32 121.1(3) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C33 C32 C31 121.0(3) . . ?
C33 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
C32 C33 C34 119.0(2) . . ?
C32 C33 H33 120.5 . . ?
C34 C33 H33 120.5 . . ?
C33 C34 C29 119.0(2) . . ?
C33 C34 C27 134.02(17) . . ?
C29 C34 C27 106.95(19) . . ?
C20 N1 C21 109.25(15) . . ?
C20 N1 H1A 125.4 . . ?
C21 N1 H1A 125.4 . . ?
C28 N2 C29 109.62(19) . . ?
C28 N2 H2A 125.2 . . ?
C29 N2 H2A 125.2 . . ?

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
C19 C1 C2 C27 106.09(17) . . . . ?
C5 C1 C2 C27 -130.20(15) . . . . ?
C19 C1 C2 C3 -128.74(16) . . . . ?
C5 C1 C2 C3 -5.02(17) . . . . ?
C27 C2 C3 C4 128.16(19) . . . . ?
C1 C2 C3 C4 4.2(2) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C3 C4 C5 C6 177.82(18) . . . . ?
C3 C4 C5 C1 -2.1(2) . . . . ?
C19 C1 C5 C6 -51.3(2) . . . . ?
C2 C1 C5 C6 -175.47(15) . . . . ?
C19 C1 C5 C4 128.68(15) . . . . ?
C2 C1 C5 C4 4.47(17) . . . . ?
C4 C5 C6 C7 -8.9(3) . . . . ?
C1 C5 C6 C7 171.07(14) . . . . ?
C4 C5 C6 C13 170.20(16) . . . . ?
C1 C5 C6 C13 -9.9(2) . . . . ?
C5 C6 C7 C12 139.66(17) . . . . ?
C13 C6 C7 C12 -39.4(2) . . . . ?
C5 C6 C7 C8 -39.8(2) . . . . ?
C13 C6 C7 C8 141.14(17) . . . . ?
C12 C7 C8 C9 -2.3(3) . . . . ?
C6 C7 C8 C9 177.16(18) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C11 1.6(4) . . . . ?
C9 C10 C11 C12 -1.4(4) . . . . ?
C10 C11 C12 C7 -0.6(3) . . . . ?
C8 C7 C12 C11 2.5(3) . . . . ?
C6 C7 C12 C11 -177.01(16) . . . . ?
C5 C6 C13 C14 114.45(18) . . . . ?
C7 C6 C13 C14 -66.4(2) . . . . ?
C5 C6 C13 C18 -63.7(2) . . . . ?
C7 C6 C13 C18 115.42(17) . . . . ?
C18 C13 C14 C15 2.0(3) . . . . ?
C6 C13 C14 C15 -176.19(16) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C16 C17 C18 C13 0.1(3) . . . . ?
C14 C13 C18 C17 -1.6(3) . . . . ?
C6 C13 C18 C17 176.64(16) . . . . ?
C5 C1 C19 C20 121.76(18) . . . . ?
C2 C1 C19 C20 -119.19(18) . . . . ?
C5 C1 C19 C22 -55.6(2) . . . . ?
C2 C1 C19 C22 63.5(2) . . . . ?
C22 C19 C20 N1 0.5(2) . . . . ?
C1 C19 C20 N1 -177.25(15) . . . . ?
N1 C21 C22 C23 179.72(15) . . . . ?
C26 C21 C22 C23 -0.8(2) . . . . ?
N1 C21 C22 C19 0.33(18) . . . . ?
C26 C21 C22 C19 179.76(16) . . . . ?
C20 C19 C22 C23 -179.78(18) . . . . ?
C1 C19 C22 C23 -2.0(3) . . . . ?
C20 C19 C22 C21 -0.53(18) . . . . ?
C1 C19 C22 C21 177.25(14) . . . . ?
C21 C22 C23 C24 0.9(3) . . . . ?
C19 C22 C23 C24 -179.92(18) . . . . ?
C22 C23 C24 C25 -0.2(3) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C24 C25 C26 C21 0.5(3) . . . . ?
N1 C21 C26 C25 179.41(19) . . . . ?
C22 C21 C26 C25 0.1(3) . . . . ?
C3 C2 C27 C28 -20.2(3) . . . . ?
C1 C2 C27 C28 98.2(2) . . . . ?
C3 C2 C27 C34 159.36(17) . . . . ?
C1 C2 C27 C34 -82.2(2) . . . . ?
C34 C27 C28 N2 -0.7(2) . . . . ?
C2 C27 C28 N2 178.95(19) . . . . ?
N2 C29 C30 C31 -179.1(2) . . . . ?
C34 C29 C30 C31 0.3(3) . . . . ?
C29 C30 C31 C32 0.4(4) . . . . ?
C30 C31 C32 C33 -0.1(4) . . . . ?
C31 C32 C33 C34 -0.7(3) . . . . ?
C32 C33 C34 C29 1.3(3) . . . . ?
C32 C33 C34 C27 -179.51(19) . . . . ?
N2 C29 C34 C33 178.37(18) . . . . ?
C30 C29 C34 C33 -1.1(3) . . . . ?
N2 C29 C34 C27 -1.0(2) . . . . ?
C30 C29 C34 C27 179.50(18) . . . . ?
C28 C27 C34 C33 -178.2(2) . . . . ?
C2 C27 C34 C33 2.2(3) . . . . ?
C28 C27 C34 C29 1.0(2) . . . . ?
C2 C27 C34 C29 -178.60(16) . . . . ?
C19 C20 N1 C21 -0.3(2) . . . . ?
C26 C21 N1 C20 -179.36(19) . . . . ?
C22 C21 N1 C20 0.0(2) . . . . ?
C27 C28 N2 C29 0.0(3) . . . . ?
C30 C29 N2 C28 -180.0(2) . . . . ?
C34 C29 N2 C28 0.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_sc_585_2
_audit_block_doi                 10.5517/cc13qq0k
_database_code_depnum_ccdc_archive 'CCDC 1034718'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        sc_585_2
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H29 N3 O4'
_chemical_formula_sum            'C23 H29 N3 O4'
_chemical_formula_weight         411.49

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   '
_symmetry_space_group_name_Hall  '-P 1  '

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

_cell_length_a                   8.5916(2)
_cell_length_b                   9.5191(3)
_cell_length_c                   14.2137(4)
_cell_angle_alpha                81.1780(10)
_cell_angle_beta                 86.5720(10)
_cell_angle_gamma                87.3920(10)
_cell_volume                     1145.87(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6522
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      24.67

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      1.192
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17414
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4025
_reflns_number_gt                3008
_reflns_threshold_expression     >2σ(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2σ(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)+(0.1074P)²+0.1548P] 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         4025
_refine_ls_number_parameters     279
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1735
_refine_ls_wR_factor_gt          0.1453
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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 0.7050(2) 0.0976(2) 0.71626(14) 0.0593(5) Uani 1 1 d . . .
H1 H 0.7958 0.1470 0.6844 0.071 Uiso 1 1 calc R . .
C2 C 0.7284(2) 0.0608(2) 0.82110(14) 0.0597(5) Uani 1 1 d . . .
C3 C 0.7959(2) 0.1479(2) 0.87941(15) 0.0637(6) Uani 1 1 d U . .
C4 C 0.8627(3) 0.2807(3) 0.8611(2) 0.0832(7) Uani 1 1 d U . .
H4 H 0.8679 0.3313 0.7997 0.100 Uiso 1 1 calc R . .
C5 C 0.9204(5) 0.3353(4) 0.9349(3) 0.1180(11) Uani 1 1 d U . .
H5 H 0.9643 0.4243 0.9233 0.142 Uiso 1 1 calc R . .
C6 C 0.9147(5) 0.2611(5) 1.0260(3) 0.1251(12) Uani 1 1 d U . .
H6 H 0.9572 0.3005 1.0743 0.150 Uiso 1 1 calc R . .
C7 C 0.8488(4) 0.1315(4) 1.0480(2) 0.1064(10) Uani 1 1 d U . .
H7 H 0.8450 0.0829 1.1100 0.128 Uiso 1 1 calc R . .
C8 C 0.7870(3) 0.0744(3) 0.97373(16) 0.0777(7) Uani 1 1 d U . .
C9 C 0.6802(5) -0.1571(4) 1.0555(2) 0.1330(14) Uani 1 1 d . . .
H9A H 0.6297 -0.2345 1.0355 0.200 Uiso 1 1 calc R . .
H9B H 0.6125 -0.1154 1.1007 0.200 Uiso 1 1 calc R . .
H9C H 0.7753 -0.1917 1.0846 0.200 Uiso 1 1 calc R . .
C10 C 0.6817(3) -0.0576(3) 0.88073(18) 0.0805(7) Uani 1 1 d . . .
H10 H 0.6334 -0.1332 0.8616 0.097 Uiso 1 1 calc R . .
C12 C 0.6766(3) -0.0300(2) 0.66940(17) 0.0785(7) Uani 1 1 d . . .
H12 H 0.7509 -0.1026 0.6635 0.094 Uiso 1 1 calc R . .
C13 C 0.5361(4) -0.0278(2) 0.63779(17) 0.0756(7) Uani 1 1 d . . .
H13 H 0.4993 -0.0991 0.6079 0.091 Uiso 1 1 calc R . .
C14 C 0.4448(3) 0.09834(19) 0.65481(14) 0.0558(5) Uani 1 1 d . . .
C15 C 0.5540(2) 0.19225(18) 0.69581(12) 0.0479(4) Uani 1 1 d . . .
H15 H 0.5069 0.2160 0.7562 0.058 Uiso 1 1 calc R . .
C16 C 0.2938(3) 0.1301(2) 0.64105(17) 0.0690(6) Uani 1 1 d . . .
C17 C 0.2162(3) 0.2651(3) 0.6648(2) 0.0892(8) Uani 1 1 d . . .
H17A H 0.2847 0.3113 0.7003 0.134 Uiso 1 1 calc R . .
H17B H 0.1212 0.2439 0.7023 0.134 Uiso 1 1 calc R . .
H17C H 0.1931 0.3269 0.6070 0.134 Uiso 1 1 calc R . .
C18 C 0.1900(4) 0.0335(3) 0.6009(3) 0.1077(10) Uani 1 1 d . . .
H18A H 0.2473 -0.0529 0.5921 0.161 Uiso 1 1 calc R . .
H18B H 0.1550 0.0800 0.5407 0.161 Uiso 1 1 calc R . .
H18C H 0.1015 0.0116 0.6443 0.161 Uiso 1 1 calc R . .
C19 C 0.5761(2) 0.45806(19) 0.65345(14) 0.0511(5) Uani 1 1 d . . .
C20 C 0.5125(4) 0.5922(3) 0.7772(2) 0.0952(9) Uani 1 1 d . . .
H20A H 0.6090 0.6428 0.7677 0.114 Uiso 1 1 calc R . .
H20B H 0.4334 0.6490 0.7410 0.114 Uiso 1 1 calc R . .
C21 C 0.4647(7) 0.5688(4) 0.8753(3) 0.1519(17) Uani 1 1 d . . .
H21A H 0.3718 0.5150 0.8843 0.228 Uiso 1 1 calc R . .
H21B H 0.4440 0.6586 0.8973 0.228 Uiso 1 1 calc R . .
H21C H 0.5461 0.5169 0.9109 0.228 Uiso 1 1 calc R . .
C22 C 0.7843(2) 0.33457(19) 0.51027(13) 0.0520(5) Uani 1 1 d . . .
C23 C 0.9673(3) 0.3561(3) 0.37953(18) 0.0812(7) Uani 1 1 d . . .
H23A H 1.0293 0.2749 0.4084 0.097 Uiso 1 1 calc R . .
H23B H 1.0100 0.4419 0.3949 0.097 Uiso 1 1 calc R . .
C24 C 0.9711(4) 0.3605(4) 0.2760(2) 0.1082(10) Uani 1 1 d . . .
H24A H 0.9302 0.2745 0.2616 0.162 Uiso 1 1 calc R . .
H24B H 1.0767 0.3692 0.2504 0.162 Uiso 1 1 calc R . .
H24C H 0.9087 0.4407 0.2482 0.162 Uiso 1 1 calc R . .
N1 N 0.58312(18) 0.32455(15) 0.63012(10) 0.0480(4) Uani 1 1 d . . .
N2 N 0.63075(18) 0.31208(16) 0.53652(10) 0.0495(4) Uani 1 1 d D . .
N3 N 0.7156(3) -0.0497(2) 0.97270(15) 0.0889(7) Uani 1 1 d . . .
O1 O 0.60128(16) 0.56490(13) 0.59785(10) 0.0630(4) Uani 1 1 d . . .
O2 O 0.5349(2) 0.45559(14) 0.74572(10) 0.0705(5) Uani 1 1 d . . .
O3 O 0.88563(17) 0.33858(17) 0.56406(11) 0.0719(5) Uani 1 1 d . . .
O4 O 0.80500(16) 0.34473(15) 0.41574(9) 0.0624(4) Uani 1 1 d . . .
H2 H 0.5520(19) 0.346(2) 0.4903(12) 0.064(6) Uiso 1 1 d D . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.501(3) . ?
C1 C12 1.507(3) . ?
C1 C15 1.561(3) . ?
C1 H1 0.9800 . ?
C2 C10 1.363(3) . ?
C2 C3 1.422(3) . ?
C3 C4 1.393(3) . ?
C3 C8 1.413(3) . ?
C4 C5 1.368(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.366(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.400(4) . ?
C7 H7 0.9300 . ?
C8 N3 1.358(4) . ?
C9 N3 1.462(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N3 1.370(3) . ?
C10 H10 0.9300 . ?
C12 C13 1.311(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.448(3) . ?
C13 H13 0.9300 . ?
C14 C16 1.338(3) . ?
C14 C15 1.524(3) . ?
C15 N1 1.470(2) . ?
C15 H15 0.9800 . ?
C16 C17 1.496(4) . ?
C16 C18 1.504(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O1 1.208(2) . ?
C19 O2 1.335(2) . ?
C19 N1 1.360(2) . ?
C20 C21 1.417(4) . ?
C20 O2 1.440(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 O3 1.198(2) . ?
C22 O4 1.334(2) . ?
C22 N2 1.367(3) . ?
C23 O4 1.460(3) . ?
C23 C24 1.464(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 N2 1.389(2) . ?
N2 H2 0.982(10) . ?

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 C12 113.32(17) . . ?
C2 C1 C15 112.00(16) . . ?
C12 C1 C15 102.36(17) . . ?
C2 C1 H1 109.6 . . ?
C12 C1 H1 109.6 . . ?
C15 C1 H1 109.6 . . ?
C10 C2 C3 106.0(2) . . ?
C10 C2 C1 127.5(2) . . ?
C3 C2 C1 126.40(18) . . ?
C4 C3 C8 119.3(2) . . ?
C4 C3 C2 133.6(2) . . ?
C8 C3 C2 107.1(2) . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 122.2(3) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C6 C7 C8 117.6(3) . . ?
C6 C7 H7 121.2 . . ?
C8 C7 H7 121.2 . . ?
N3 C8 C7 131.4(3) . . ?
N3 C8 C3 107.8(2) . . ?
C7 C8 C3 120.8(3) . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 N3 110.6(2) . . ?
C2 C10 H10 124.7 . . ?
N3 C10 H10 124.7 . . ?
C13 C12 C1 113.0(2) . . ?
C13 C12 H12 123.5 . . ?
C1 C12 H12 123.5 . . ?
C12 C13 C14 112.2(2) . . ?
C12 C13 H13 123.9 . . ?
C14 C13 H13 123.9 . . ?
C16 C14 C13 128.9(2) . . ?
C16 C14 C15 124.62(19) . . ?
C13 C14 C15 106.45(19) . . ?
N1 C15 C14 111.51(14) . . ?
N1 C15 C1 113.12(15) . . ?
C14 C15 C1 105.01(15) . . ?
N1 C15 H15 109.0 . . ?
C14 C15 H15 109.0 . . ?
C1 C15 H15 109.0 . . ?
C14 C16 C17 122.0(2) . . ?
C14 C16 C18 122.8(2) . . ?
C17 C16 C18 115.3(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 O2 124.47(18) . . ?
O1 C19 N1 124.59(18) . . ?
O2 C19 N1 110.93(15) . . ?
C21 C20 O2 107.9(2) . . ?
C21 C20 H20A 110.1 . . ?
O2 C20 H20A 110.1 . . ?
C21 C20 H20B 110.1 . . ?
O2 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?
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 . . ?
O3 C22 O4 125.28(19) . . ?
O3 C22 N2 125.29(18) . . ?
O4 C22 N2 109.36(16) . . ?
O4 C23 C24 107.9(2) . . ?
O4 C23 H23A 110.1 . . ?
C24 C23 H23A 110.1 . . ?
O4 C23 H23B 110.1 . . ?
C24 C23 H23B 110.1 . . ?
H23A C23 H23B 108.4 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 N1 N2 116.57(14) . . ?
C19 N1 C15 126.09(15) . . ?
N2 N1 C15 117.23(14) . . ?
C22 N2 N1 116.82(15) . . ?
C22 N2 H2 118.5(12) . . ?
N1 N2 H2 113.9(13) . . ?
C8 N3 C10 108.45(19) . . ?
C8 N3 C9 126.0(3) . . ?
C10 N3 C9 125.5(3) . . ?
C19 O2 C20 115.87(17) . . ?
C22 O4 C23 114.56(17) . . ?

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
C12 C1 C2 C10 -21.6(3) . . . . ?
C15 C1 C2 C10 93.6(3) . . . . ?
C12 C1 C2 C3 162.6(2) . . . . ?
C15 C1 C2 C3 -82.2(2) . . . . ?
C10 C2 C3 C4 -179.4(3) . . . . ?
C1 C2 C3 C4 -2.9(4) . . . . ?
C10 C2 C3 C8 0.5(2) . . . . ?
C1 C2 C3 C8 176.96(19) . . . . ?
C8 C3 C4 C5 1.1(4) . . . . ?
C2 C3 C4 C5 -179.0(3) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C4 C5 C6 C7 -1.4(6) . . . . ?
C5 C6 C7 C8 0.5(6) . . . . ?
C6 C7 C8 N3 179.8(3) . . . . ?
C6 C7 C8 C3 1.2(4) . . . . ?
C4 C3 C8 N3 179.0(2) . . . . ?
C2 C3 C8 N3 -0.9(3) . . . . ?
C4 C3 C8 C7 -2.0(4) . . . . ?
C2 C3 C8 C7 178.0(2) . . . . ?
C3 C2 C10 N3 0.1(3) . . . . ?
C1 C2 C10 N3 -176.3(2) . . . . ?
C2 C1 C12 C13 114.1(2) . . . . ?
C15 C1 C12 C13 -6.7(3) . . . . ?
C1 C12 C13 C14 0.9(3) . . . . ?
C12 C13 C14 C16 -172.8(2) . . . . ?
C12 C13 C14 C15 5.5(3) . . . . ?
C16 C14 C15 N1 -67.9(2) . . . . ?
C13 C14 C15 N1 113.61(17) . . . . ?
C16 C14 C15 C1 169.21(19) . . . . ?
C13 C14 C15 C1 -9.3(2) . . . . ?
C2 C1 C15 N1 125.81(17) . . . . ?
C12 C1 C15 N1 -112.47(17) . . . . ?
C2 C1 C15 C14 -112.37(18) . . . . ?
C12 C1 C15 C14 9.35(19) . . . . ?
C13 C14 C16 C17 178.5(2) . . . . ?
C15 C14 C16 C17 0.4(3) . . . . ?
C13 C14 C16 C18 -1.5(4) . . . . ?
C15 C14 C16 C18 -179.6(2) . . . . ?
O1 C19 N1 N2 3.6(3) . . . . ?
O2 C19 N1 N2 -177.60(15) . . . . ?
O1 C19 N1 C15 179.70(17) . . . . ?
O2 C19 N1 C15 -1.5(3) . . . . ?
C14 C15 N1 C19 132.55(19) . . . . ?
C1 C15 N1 C19 -109.4(2) . . . . ?
C14 C15 N1 N2 -51.3(2) . . . . ?
C1 C15 N1 N2 66.8(2) . . . . ?
O3 C22 N2 N1 14.2(3) . . . . ?
O4 C22 N2 N1 -168.68(14) . . . . ?
C19 N1 N2 C22 70.9(2) . . . . ?
C15 N1 N2 C22 -105.62(18) . . . . ?
C7 C8 N3 C10 -177.8(3) . . . . ?
C3 C8 N3 C10 0.9(3) . . . . ?
C7 C8 N3 C9 2.3(5) . . . . ?
C3 C8 N3 C9 -178.9(3) . . . . ?
C2 C10 N3 C8 -0.6(3) . . . . ?
C2 C10 N3 C9 179.2(3) . . . . ?
O1 C19 O2 C20 3.3(3) . . . . ?
N1 C19 O2 C20 -175.6(2) . . . . ?
C21 C20 O2 C19 178.1(3) . . . . ?
O3 C22 O4 C23 2.4(3) . . . . ?
N2 C22 O4 C23 -174.74(17) . . . . ?
C24 C23 O4 C22 177.8(2) . . . . ?

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
C1 H1 O3 0.98 2.42 3.279(2) 145.9 .
C23 H23B O3 0.97 2.47 3.444(3) 178.9 2_766
N2 H2 O1 0.982(10) 1.946(10) 2.924(2) 173.8(18) 2_666

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.125
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
