# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_pblr120703
_database_code_depnum_ccdc_archive 'CCDC 1531548'
_audit_update_record             
;
2017-02-07 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 N4 O2'
_chemical_formula_sum            'C20 H20 N4 O2'
_chemical_formula_weight         348.40

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                   9.4739(8)
_cell_length_b                   10.4564(10)
_cell_length_c                   10.8136(16)
_cell_angle_alpha                109.389(3)
_cell_angle_beta                 110.956(2)
_cell_angle_gamma                104.273(2)
_cell_volume                     858.68(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2297
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      28.66

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9840
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  triumph
_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            10895
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0604
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         29.03
_reflns_number_total             4555
_reflns_number_gt                2732
_reflns_threshold_expression     I>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)+(0.0488P)²+0.1428P] 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         4555
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 1.01687(18) 0.96947(18) 0.83316(18) 0.0237(4) Uani 1 1 d . . .
H1 H 0.9296 0.8724 0.7698 0.028 Uiso 1 1 calc R . .
C2 C 0.98081(17) 1.09261(18) 0.87268(17) 0.0219(3) Uani 1 1 d . . .
C3 C 1.11798(19) 1.25011(19) 0.97431(18) 0.0262(4) Uani 1 1 d . . .
C4 C 1.28206(19) 1.26344(19) 1.02805(19) 0.0280(4) Uani 1 1 d . . .
H4 H 1.3695 1.3596 1.0968 0.034 Uiso 1 1 calc R . .
C5 C 1.32329(18) 1.14338(19) 0.98594(18) 0.0257(4) Uani 1 1 d . . .
C6 C 1.18170(18) 0.98877(18) 0.88684(17) 0.0230(4) Uani 1 1 d . . .
C7 C 0.67882(17) 0.94896(18) 0.74744(18) 0.0251(4) Uani 1 1 d . . .
H7A H 0.5958 0.9690 0.7769 0.030 Uiso 1 1 calc R . .
H7B H 0.7051 0.8747 0.7779 0.030 Uiso 1 1 calc R . .
C8 C 0.60039(17) 0.88073(17) 0.57916(17) 0.0217(3) Uani 1 1 d . . .
C9 C 0.66628(18) 0.93483(18) 0.50196(18) 0.0247(4) Uani 1 1 d . . .
H9 H 0.7716 1.0170 0.5561 0.030 Uiso 1 1 calc R . .
C10 C 0.58157(19) 0.87142(19) 0.34724(19) 0.0267(4) Uani 1 1 d . . .
H10 H 0.6299 0.9100 0.2968 0.032 Uiso 1 1 calc R . .
C11 C 0.42583(18) 0.75133(18) 0.26495(18) 0.0242(4) Uani 1 1 d . . .
C12 C 0.36170(19) 0.69309(19) 0.34146(19) 0.0282(4) Uani 1 1 d . . .
H12 H 0.2578 0.6092 0.2875 0.034 Uiso 1 1 calc R . .
C13 C 0.44828(18) 0.75656(19) 0.49535(19) 0.0274(4) Uani 1 1 d . . .
H13 H 0.4031 0.7146 0.5455 0.033 Uiso 1 1 calc R . .
C14 C 1.1187(2) 0.72019(19) 0.7722(2) 0.0306(4) Uani 1 1 d . . .
H14A H 1.0531 0.6939 0.8207 0.037 Uiso 1 1 calc R . .
H14B H 1.1864 0.6616 0.7715 0.037 Uiso 1 1 calc R . .
C15 C 1.00182(19) 0.67839(18) 0.61356(19) 0.0261(4) Uani 1 1 d . . .
C16 C 1.0595(2) 0.7141(2) 0.5227(2) 0.0353(4) Uani 1 1 d . . .
H16 H 1.1757 0.7637 0.5610 0.042 Uiso 1 1 calc R . .
C17 C 0.9528(2) 0.6794(2) 0.3787(2) 0.0360(4) Uani 1 1 d . . .
H17 H 0.9961 0.7040 0.3187 0.043 Uiso 1 1 calc R . .
C18 C 0.7815(2) 0.60822(18) 0.32040(19) 0.0287(4) Uani 1 1 d . . .
C19 C 0.7222(2) 0.5704(2) 0.4093(2) 0.0318(4) Uani 1 1 d . . .
H19 H 0.6061 0.5203 0.3709 0.038 Uiso 1 1 calc R . .
C20 C 0.83095(19) 0.60511(19) 0.5533(2) 0.0293(4) Uani 1 1 d . . .
H20 H 0.7880 0.5783 0.6125 0.035 Uiso 1 1 calc R . .
N1 N 0.82916(15) 1.08621(16) 0.83049(15) 0.0242(3) Uani 1 1 d . . .
N2 N 0.3295(2) 0.6956(2) 0.11037(18) 0.0329(4) Uani 1 1 d . . .
N3 N 1.22990(16) 0.87960(16) 0.86037(16) 0.0272(3) Uani 1 1 d . . .
N4 N 0.6724(2) 0.57119(19) 0.17335(18) 0.0394(4) Uani 1 1 d . . .
O1 O 1.07439(14) 1.35461(13) 1.00044(15) 0.0403(3) Uani 1 1 d . . .
O2 O 1.46787(13) 1.15111(14) 1.02296(14) 0.0359(3) Uani 1 1 d . . .
H1N H 0.822(2) 1.171(2) 0.865(2) 0.033(5) Uiso 1 1 d . . .
H3N H 1.344(2) 0.906(2) 0.907(2) 0.046(6) Uiso 1 1 d . . .
H2A H 0.388(2) 0.714(2) 0.068(2) 0.046(6) Uiso 1 1 d . . .
H2B H 0.256(3) 0.606(2) 0.068(2) 0.045(6) Uiso 1 1 d . . .
H4A H 0.716(3) 0.626(3) 0.135(3) 0.075(8) Uiso 1 1 d . . .
H4B H 0.569(3) 0.569(3) 0.158(3) 0.074(8) Uiso 1 1 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 1.383(2) . ?
C1 C6 1.391(2) . ?
C1 H1 0.9500 . ?
C2 N1 1.3191(18) . ?
C2 C3 1.526(2) . ?
C3 O1 1.2432(19) . ?
C3 C4 1.402(2) . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 O2 1.2549(17) . ?
C5 C6 1.521(2) . ?
C6 N3 1.314(2) . ?
C7 N1 1.455(2) . ?
C7 C8 1.511(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.385(2) . ?
C8 C13 1.395(2) . ?
C9 C10 1.387(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.397(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(2) . ?
C11 N2 1.402(2) . ?
C12 C13 1.380(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 N3 1.469(2) . ?
C14 C15 1.505(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.389(2) . ?
C15 C20 1.391(2) . ?
C16 C17 1.378(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.395(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(2) . ?
C18 N4 1.402(2) . ?
C19 C20 1.383(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
N1 H1N 0.870(19) . ?
N2 H2A 0.86(2) . ?
N2 H2B 0.86(2) . ?
N3 H3N 0.932(19) . ?
N4 H4A 0.91(3) . ?
N4 H4B 0.93(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
C2 C1 C6 119.55(15) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
N1 C2 C1 124.31(15) . . ?
N1 C2 C3 114.14(14) . . ?
C1 C2 C3 121.54(13) . . ?
O1 C3 C4 126.02(16) . . ?
O1 C3 C2 117.25(14) . . ?
C4 C3 C2 116.73(15) . . ?
C5 C4 C3 123.37(15) . . ?
C5 C4 H4 118.3 . . ?
C3 C4 H4 118.3 . . ?
O2 C5 C4 125.60(16) . . ?
O2 C5 C6 116.90(15) . . ?
C4 C5 C6 117.50(13) . . ?
N3 C6 C1 124.58(15) . . ?
N3 C6 C5 114.29(13) . . ?
C1 C6 C5 121.12(14) . . ?
N1 C7 C8 115.83(13) . . ?
N1 C7 H7A 108.3 . . ?
C8 C7 H7A 108.3 . . ?
N1 C7 H7B 108.3 . . ?
C8 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C9 C8 C13 117.57(15) . . ?
C9 C8 C7 124.78(14) . . ?
C13 C8 C7 117.62(14) . . ?
C8 C9 C10 121.33(15) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C11 120.54(15) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 118.37(15) . . ?
C12 C11 N2 119.78(15) . . ?
C10 C11 N2 121.72(16) . . ?
C13 C12 C11 120.34(15) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C8 121.75(16) . . ?
C12 C13 H13 119.1 . . ?
C8 C13 H13 119.1 . . ?
N3 C14 C15 112.62(14) . . ?
N3 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
N3 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C20 117.40(16) . . ?
C16 C15 C14 121.56(15) . . ?
C20 C15 C14 121.02(15) . . ?
C17 C16 C15 121.81(16) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C18 120.26(17) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 118.55(17) . . ?
C19 C18 N4 120.90(16) . . ?
C17 C18 N4 120.52(17) . . ?
C20 C19 C18 120.50(15) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C15 121.46(16) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
C2 N1 C7 124.58(14) . . ?
C2 N1 H1N 116.2(12) . . ?
C7 N1 H1N 118.8(12) . . ?
C11 N2 H2A 112.9(13) . . ?
C11 N2 H2B 112.4(14) . . ?
H2A N2 H2B 116.5(19) . . ?
C6 N3 C14 125.25(13) . . ?
C6 N3 H3N 116.8(12) . . ?
C14 N3 H3N 117.8(12) . . ?
C18 N4 H4A 114.4(16) . . ?
C18 N4 H4B 114.4(15) . . ?
H4A N4 H4B 111(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
C6 C1 C2 N1 -178.51(15) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
N1 C2 C3 O1 -3.5(2) . . . . ?
C1 C2 C3 O1 177.89(15) . . . . ?
N1 C2 C3 C4 177.33(15) . . . . ?
C1 C2 C3 C4 -1.3(2) . . . . ?
O1 C3 C4 C5 -174.94(17) . . . . ?
C2 C3 C4 C5 4.2(2) . . . . ?
C3 C4 C5 O2 174.87(16) . . . . ?
C3 C4 C5 C6 -5.4(2) . . . . ?
C2 C1 C6 N3 177.70(15) . . . . ?
C2 C1 C6 C5 -1.2(2) . . . . ?
O2 C5 C6 N3 4.6(2) . . . . ?
C4 C5 C6 N3 -175.20(15) . . . . ?
O2 C5 C6 C1 -176.39(15) . . . . ?
C4 C5 C6 C1 3.8(2) . . . . ?
N1 C7 C8 C9 3.7(2) . . . . ?
N1 C7 C8 C13 -174.44(14) . . . . ?
C13 C8 C9 C10 2.3(2) . . . . ?
C7 C8 C9 C10 -175.89(14) . . . . ?
C8 C9 C10 C11 0.6(2) . . . . ?
C9 C10 C11 C12 -2.8(2) . . . . ?
C9 C10 C11 N2 172.93(15) . . . . ?
C10 C11 C12 C13 2.2(2) . . . . ?
N2 C11 C12 C13 -173.64(15) . . . . ?
C11 C12 C13 C8 0.7(2) . . . . ?
C9 C8 C13 C12 -2.9(2) . . . . ?
C7 C8 C13 C12 175.39(14) . . . . ?
N3 C14 C15 C16 53.3(2) . . . . ?
N3 C14 C15 C20 -125.30(17) . . . . ?
C20 C15 C16 C17 0.3(3) . . . . ?
C14 C15 C16 C17 -178.35(16) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C16 C17 C18 C19 -1.6(3) . . . . ?
C16 C17 C18 N4 -179.30(17) . . . . ?
C17 C18 C19 C20 1.1(3) . . . . ?
N4 C18 C19 C20 178.88(16) . . . . ?
C18 C19 C20 C15 0.0(3) . . . . ?
C16 C15 C20 C19 -0.7(2) . . . . ?
C14 C15 C20 C19 177.93(16) . . . . ?
C1 C2 N1 C7 5.6(3) . . . . ?
C3 C2 N1 C7 -173.02(14) . . . . ?
C8 C7 N1 C2 -89.33(18) . . . . ?
C1 C6 N3 C14 -0.9(3) . . . . ?
C5 C6 N3 C14 178.03(15) . . . . ?
C15 C14 N3 C6 60.2(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
N1 H1N N2 0.870(19) 2.256(19) 3.048(2) 151.2(16) 2_676
N2 H2A O2 0.86(2) 2.40(2) 3.214(2) 157.7(18) 2_776
N2 H2B O1 0.86(2) 2.45(2) 3.294(2) 168.1(19) 1_444
N3 H3N O2 0.932(19) 1.99(2) 2.8340(17) 149.3(17) 2_877

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        29.03
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_pblr140716
_database_code_depnum_ccdc_archive 'CCDC 1531546'
_audit_update_record             
;
2017-02-07 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 N2 O2'
_chemical_formula_sum            'C22 H22 N2 O2'
_chemical_formula_weight         346.41

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   12.666(2)
_cell_length_b                   13.200(3)
_cell_length_c                   13.728(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2295.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1478
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      21.25

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.002
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6225
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus 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            16743
_diffrn_reflns_av_unetI/netI     0.1671
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.140
_diffrn_reflns_theta_max         28.022
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5471
_reflns_number_gt                2056
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_max     0.971
_reflns_Friedel_fraction_full    0.982

_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-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1394P)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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 602 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -2.6(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5471
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2113
_refine_ls_R_factor_gt           0.0921
_refine_ls_wR_factor_ref         0.2808
_refine_ls_wR_factor_gt          0.2355
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_restrained_S_all      0.927
_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_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 0.1433(4) 0.0660(5) 0.7846(5) 0.0415(16) Uani 1 1 d . . . . .
C2 C 0.1841(5) -0.0421(6) 0.7780(4) 0.0414(17) Uani 1 1 d . . . . .
C3 C 0.2422(5) -0.0802(6) 0.8558(5) 0.0539(19) Uani 1 1 d . . . . .
H3 H 0.2685 -0.1475 0.8525 0.065 Uiso 1 1 calc R U . . .
C4 C 0.2632(5) -0.0212(6) 0.9399(4) 0.0465(18) Uani 1 1 d . . . . .
C5 C 0.2270(4) 0.0878(6) 0.9378(4) 0.0453(18) Uani 1 1 d . . . . .
C6 C 0.1657(4) 0.1268(5) 0.8625(4) 0.0367(15) Uani 1 1 d . . . . .
H6 H 0.1399 0.1944 0.8652 0.044 Uiso 1 1 calc R U . . .
C7 C 0.0441(5) 0.1931(7) 0.6927(5) 0.059(2) Uani 1 1 d . . . . .
H7 H -0.0040 0.2050 0.7494 0.071 Uiso 1 1 calc R U . . .
C8 C -0.0235(6) 0.1889(8) 0.5989(6) 0.079(3) Uani 1 1 d . . . . .
H8A H -0.0310 0.1184 0.5778 0.118 Uiso 1 1 calc R U . . .
H8B H 0.0112 0.2282 0.5474 0.118 Uiso 1 1 calc R U . . .
H8C H -0.0934 0.2176 0.6119 0.118 Uiso 1 1 calc R U . . .
C9 C 0.1228(6) 0.2783(8) 0.6885(5) 0.068(3) Uani 1 1 d . . . . .
C10 C 0.0976(6) 0.3737(7) 0.7338(6) 0.061(2) Uani 1 1 d . . . . .
H10 H 0.0314 0.3832 0.7651 0.074 Uiso 1 1 calc R U . . .
C11 C 0.1682(8) 0.4483(8) 0.7313(7) 0.087(3) Uani 1 1 d . . . . .
H11 H 0.1539 0.5098 0.7647 0.105 Uiso 1 1 calc R U . . .
C12 C 0.2621(10) 0.4378(9) 0.6810(7) 0.103(4) Uani 1 1 d . . . . .
H12 H 0.3089 0.4939 0.6775 0.124 Uiso 1 1 calc R U . . .
C13 C 0.2899(7) 0.3480(9) 0.6356(6) 0.083(3) Uani 1 1 d . . . . .
H13 H 0.3556 0.3410 0.6030 0.100 Uiso 1 1 calc R U . . .
C14 C 0.2191(5) 0.2693(6) 0.6393(6) 0.062(2) Uani 1 1 d . . . . .
H14 H 0.2359 0.2073 0.6077 0.074 Uiso 1 1 calc R U . . .
C15 C 0.2565(6) 0.2534(6) 1.0172(5) 0.057(2) Uani 1 1 d . . . . .
H15 H 0.2592 0.2812 0.9495 0.069 Uiso 1 1 calc R U . . .
C16 C 0.3534(6) 0.2945(7) 1.0722(5) 0.069(2) Uani 1 1 d . . . . .
H16A H 0.3480 0.3684 1.0778 0.103 Uiso 1 1 calc R U . . .
H16B H 0.4178 0.2770 1.0363 0.103 Uiso 1 1 calc R U . . .
H16C H 0.3562 0.2645 1.1374 0.103 Uiso 1 1 calc R U . . .
C17 C 0.1557(4) 0.2854(6) 1.0606(4) 0.1108(18) Uani 1 1 d G . . . .
C18 C 0.1139(5) 0.2341(5) 1.1401(5) 0.1108(18) Uani 1 1 d G . . . .
H18 H 0.1474 0.1745 1.1637 0.133 Uiso 1 1 calc R U . . .
C19 C 0.0230(5) 0.2699(6) 1.1853(4) 0.1108(18) Uani 1 1 d G . . . .
H19 H -0.0055 0.2349 1.2397 0.133 Uiso 1 1 calc R U . . .
C20 C -0.0260(4) 0.3571(6) 1.1509(4) 0.1108(18) Uani 1 1 d G . . . .
H20 H -0.0881 0.3815 1.1817 0.133 Uiso 1 1 calc R U . . .
C21 C 0.0158(5) 0.4084(5) 1.0713(5) 0.1108(18) Uani 1 1 d G . . . .
H21 H -0.0177 0.4679 1.0478 0.133 Uiso 1 1 calc R U . . .
C22 C 0.1066(5) 0.3725(6) 1.0261(4) 0.1108(18) Uani 1 1 d G . . . .
H22 H 0.1352 0.4076 0.9718 0.133 Uiso 1 1 calc R U . . .
N1 N 0.0949(4) 0.0961(5) 0.7054(4) 0.0482(15) Uani 1 1 d . . . . .
H1N H 0.0933 0.0538 0.6559 0.058 Uiso 1 1 calc R U . . .
N2 N 0.2670(4) 0.1436(5) 1.0101(3) 0.0510(16) Uani 1 1 d . . . . .
H2N H 0.3019 0.1121 1.0564 0.061 Uiso 1 1 calc R U . . .
O1 O 0.1596(4) -0.0908(4) 0.7034(3) 0.0600(14) Uani 1 1 d . . . . .
O2 O 0.3179(4) -0.0493(4) 1.0103(3) 0.0585(14) 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 N1 1.310(8) . ?
C1 C6 1.367(9) . ?
C1 C2 1.520(9) . ?
C2 O1 1.248(7) . ?
C2 C3 1.391(9) . ?
C3 C4 1.418(9) . ?
C3 H3 0.9500 . ?
C4 O2 1.246(8) . ?
C4 C5 1.510(10) . ?
C5 N2 1.335(8) . ?
C5 C6 1.392(8) . ?
C6 H6 0.9500 . ?
C7 N1 1.444(10) . ?
C7 C9 1.504(11) . ?
C7 C8 1.548(10) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C14 1.400(9) . ?
C9 C10 1.441(12) . ?
C10 C11 1.332(12) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(13) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(13) . ?
C12 H12 0.9500 . ?
C13 C14 1.373(12) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 N2 1.458(9) . ?
C15 C17 1.471(8) . ?
C15 C16 1.540(10) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.3900 . ?
C17 C22 1.3900 . ?
C18 C19 1.3900 . ?
C18 H18 0.9500 . ?
C19 C20 1.3900 . ?
C19 H19 0.9500 . ?
C20 C21 1.3900 . ?
C20 H20 0.9500 . ?
C21 C22 1.3900 . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
N1 H1N 0.8800 . ?
N2 H2N 0.8800 . ?

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 C1 C6 124.6(6) . . ?
N1 C1 C2 113.3(5) . . ?
C6 C1 C2 121.8(5) . . ?
O1 C2 C3 125.1(7) . . ?
O1 C2 C1 116.6(5) . . ?
C3 C2 C1 118.3(5) . . ?
C2 C3 C4 121.7(7) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
O2 C4 C3 125.0(7) . . ?
O2 C4 C5 117.8(6) . . ?
C3 C4 C5 116.8(6) . . ?
N2 C5 C6 124.0(7) . . ?
N2 C5 C4 113.4(6) . . ?
C6 C5 C4 122.4(6) . . ?
C1 C6 C5 118.6(6) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N1 C7 C9 111.8(6) . . ?
N1 C7 C8 108.4(7) . . ?
C9 C7 C8 111.1(7) . . ?
N1 C7 H7 108.5 . . ?
C9 C7 H7 108.5 . . ?
C8 C7 H7 108.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 118.4(8) . . ?
C14 C9 C7 122.3(8) . . ?
C10 C9 C7 119.3(7) . . ?
C11 C10 C9 119.1(8) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 121.2(10) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 121.9(10) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C14 C13 C12 117.7(8) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
C13 C14 C9 121.5(8) . . ?
C13 C14 H14 119.2 . . ?
C9 C14 H14 119.2 . . ?
N2 C15 C17 113.0(6) . . ?
N2 C15 C16 108.1(6) . . ?
C17 C15 C16 113.1(6) . . ?
N2 C15 H15 107.4 . . ?
C17 C15 H15 107.4 . . ?
C16 C15 H15 107.4 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 120.0 . . ?
C18 C17 C15 120.6(5) . . ?
C22 C17 C15 119.2(5) . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 120.0 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 120.0 . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
C1 N1 C7 125.3(6) . . ?
C1 N1 H1N 117.3 . . ?
C7 N1 H1N 117.3 . . ?
C5 N2 C15 124.3(6) . . ?
C5 N2 H2N 117.8 . . ?
C15 N2 H2N 117.8 . . ?

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 C1 C2 O1 -5.7(8) . . . . ?
C6 C1 C2 O1 -179.6(5) . . . . ?
N1 C1 C2 C3 176.3(5) . . . . ?
C6 C1 C2 C3 2.5(9) . . . . ?
O1 C2 C3 C4 -177.3(6) . . . . ?
C1 C2 C3 C4 0.4(9) . . . . ?
C2 C3 C4 O2 -177.1(6) . . . . ?
C2 C3 C4 C5 -4.8(9) . . . . ?
O2 C4 C5 N2 5.3(8) . . . . ?
C3 C4 C5 N2 -167.6(6) . . . . ?
O2 C4 C5 C6 179.9(6) . . . . ?
C3 C4 C5 C6 7.0(8) . . . . ?
N1 C1 C6 C5 -173.5(5) . . . . ?
C2 C1 C6 C5 -0.4(8) . . . . ?
N2 C5 C6 C1 169.6(6) . . . . ?
C4 C5 C6 C1 -4.4(8) . . . . ?
N1 C7 C9 C14 39.7(9) . . . . ?
C8 C7 C9 C14 -81.6(9) . . . . ?
N1 C7 C9 C10 -142.2(7) . . . . ?
C8 C7 C9 C10 96.5(8) . . . . ?
C14 C9 C10 C11 -3.0(12) . . . . ?
C7 C9 C10 C11 178.8(7) . . . . ?
C9 C10 C11 C12 4.0(13) . . . . ?
C10 C11 C12 C13 -3.7(15) . . . . ?
C11 C12 C13 C14 2.1(14) . . . . ?
C12 C13 C14 C9 -1.1(13) . . . . ?
C10 C9 C14 C13 1.5(12) . . . . ?
C7 C9 C14 C13 179.6(8) . . . . ?
N2 C15 C17 C18 41.2(7) . . . . ?
C16 C15 C17 C18 -82.1(7) . . . . ?
N2 C15 C17 C22 -143.9(5) . . . . ?
C16 C15 C17 C22 92.8(7) . . . . ?
C22 C17 C18 C19 0.0 . . . . ?
C15 C17 C18 C19 174.8(6) . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C20 C21 C22 C17 0.0 . . . . ?
C18 C17 C22 C21 0.0 . . . . ?
C15 C17 C22 C21 -174.9(6) . . . . ?
C6 C1 N1 C7 -9.5(10) . . . . ?
C2 C1 N1 C7 176.9(6) . . . . ?
C9 C7 N1 C1 69.5(8) . . . . ?
C8 C7 N1 C1 -167.7(6) . . . . ?
C6 C5 N2 C15 -3.3(9) . . . . ?
C4 C5 N2 C15 171.2(6) . . . . ?
C17 C15 N2 C5 83.1(7) . . . . ?
C16 C15 N2 C5 -150.9(6) . . . . ?

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
N2 H2N O1 0.88 2.09 2.898(6) 151.3 4
N1 H1N O2 0.88 2.29 2.961(7) 132.7 4_554

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.057

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.059 -0.058 0.097 133.9 45.2
2 0.059 0.442 0.403 133.8 45.1
3 0.441 0.558 0.903 133.9 45.2
4 0.559 0.058 0.597 133.9 45.1
_platon_squeeze_details          
;
 The residual electron density was assigned to a molecule of the pentane
 solvent [181/4 = 45 e par asymmetric unit; one molecule of C5H12
 would give 42e].
;

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_pblr110323_02
_database_code_depnum_ccdc_archive 'CCDC 1531551'
_audit_update_record             
;
2017-02-07 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 N2 O2'
_chemical_formula_sum            'C24 H26 N2 O2'
_chemical_formula_weight         374.47

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                   7.9425(3)
_cell_length_b                   11.2305(5)
_cell_length_c                   12.3864(5)
_cell_angle_alpha                69.7420(10)
_cell_angle_beta                 88.5510(10)
_cell_angle_gamma                74.2780(10)
_cell_volume                     994.85(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4850
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      29.93

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9804
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  triumph
_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            15982
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         30.07
_reflns_number_total             5808
_reflns_number_gt                3836
_reflns_threshold_expression     I>2sigma(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 > 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)+(0.0616P)²+0.0531P] 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         5808
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1208
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.04172(14) 0.88815(12) 0.22138(9) 0.0230(2) Uani 1 1 d . . .
H1 H 0.0632 0.8311 0.2088 0.028 Uiso 1 1 calc R . .
C2 C -0.19033(14) 0.93196(11) 0.14620(9) 0.0212(2) Uani 1 1 d . . .
C3 C -0.35951(14) 1.02384(11) 0.16516(9) 0.0225(2) Uani 1 1 d . . .
C4 C -0.35735(14) 1.07037(12) 0.25587(10) 0.0249(2) Uani 1 1 d . . .
H4 H -0.4599 1.1320 0.2653 0.030 Uiso 1 1 calc R . .
C5 C -0.21110(14) 1.03022(12) 0.33320(10) 0.0235(2) Uani 1 1 d . . .
C6 C -0.04950(14) 0.92946(11) 0.31583(9) 0.0210(2) Uani 1 1 d . . .
C7 C -0.05380(15) 0.81273(12) 0.01918(10) 0.0258(3) Uani 1 1 d . . .
H7A H -0.0053 0.7294 0.0849 0.031 Uiso 1 1 calc R . .
H7B H 0.0402 0.8572 -0.0038 0.031 Uiso 1 1 calc R . .
C8 C -0.11203(16) 0.78163(13) -0.08120(10) 0.0288(3) Uani 1 1 d . . .
H8A H -0.1674 0.8653 -0.1450 0.035 Uiso 1 1 calc R . .
H8B H -0.2011 0.7326 -0.0566 0.035 Uiso 1 1 calc R . .
C9 C 0.04095(15) 0.69961(13) -0.12471(10) 0.0289(3) Uani 1 1 d . . .
H9A H 0.1282 0.7501 -0.1507 0.035 Uiso 1 1 calc R . .
H9B H 0.0983 0.6176 -0.0598 0.035 Uiso 1 1 calc R . .
C10 C -0.01083(14) 0.66257(12) -0.22278(10) 0.0250(2) Uani 1 1 d . . .
C11 C 0.05624(16) 0.53497(13) -0.22257(11) 0.0324(3) Uani 1 1 d . . .
H11 H 0.1337 0.4704 -0.1597 0.039 Uiso 1 1 calc R . .
C12 C 0.01192(17) 0.50018(14) -0.31277(12) 0.0388(3) Uani 1 1 d . . .
H12 H 0.0594 0.4123 -0.3112 0.047 Uiso 1 1 calc R . .
C13 C -0.10047(17) 0.59220(15) -0.40462(12) 0.0372(3) Uani 1 1 d . . .
H13 H -0.1311 0.5679 -0.4661 0.045 Uiso 1 1 calc R . .
C14 C -0.16815(17) 0.71975(14) -0.40667(11) 0.0345(3) Uani 1 1 d . . .
H14 H -0.2456 0.7838 -0.4698 0.041 Uiso 1 1 calc R . .
C15 C -0.12323(17) 0.75483(13) -0.31649(11) 0.0313(3) Uani 1 1 d . . .
H15 H -0.1700 0.8431 -0.3189 0.038 Uiso 1 1 calc R . .
C16 C 0.23911(14) 0.78284(12) 0.40927(10) 0.0249(2) Uani 1 1 d . . .
H16A H 0.2186 0.7190 0.3761 0.030 Uiso 1 1 calc R . .
H16B H 0.2783 0.7343 0.4919 0.030 Uiso 1 1 calc R . .
C17 C 0.38208(15) 0.84023(12) 0.34782(11) 0.0290(3) Uani 1 1 d . . .
H17A H 0.4151 0.8937 0.3882 0.035 Uiso 1 1 calc R . .
H17B H 0.3370 0.8992 0.2680 0.035 Uiso 1 1 calc R . .
C18 C 0.54469(15) 0.73077(12) 0.34433(11) 0.0293(3) Uani 1 1 d . . .
H18A H 0.6398 0.7710 0.3118 0.035 Uiso 1 1 calc R . .
H18B H 0.5855 0.6695 0.4241 0.035 Uiso 1 1 calc R . .
C19 C 0.51035(15) 0.65331(12) 0.27334(11) 0.0278(3) Uani 1 1 d . . .
C20 C 0.5196(2) 0.52091(14) 0.32390(13) 0.0408(3) Uani 1 1 d . . .
H20 H 0.5493 0.4780 0.4045 0.049 Uiso 1 1 calc R . .
C21 C 0.4863(2) 0.44942(17) 0.25957(16) 0.0569(5) Uani 1 1 d . . .
H21 H 0.4946 0.3582 0.2957 0.068 Uiso 1 1 calc R . .
C22 C 0.4411(2) 0.51181(19) 0.14225(16) 0.0555(5) Uani 1 1 d . . .
H22 H 0.4154 0.4641 0.0978 0.067 Uiso 1 1 calc R . .
C23 C 0.43351(19) 0.64377(17) 0.09017(14) 0.0474(4) Uani 1 1 d . . .
H23 H 0.4048 0.6864 0.0094 0.057 Uiso 1 1 calc R . .
C24 C 0.46742(17) 0.71401(14) 0.15499(11) 0.0353(3) Uani 1 1 d . . .
H24 H 0.4614 0.8048 0.1184 0.042 Uiso 1 1 calc R . .
N1 N -0.20023(13) 0.89807(10) 0.05527(8) 0.0244(2) Uani 1 1 d . . .
N2 N 0.07553(12) 0.88519(10) 0.39895(8) 0.0246(2) Uani 1 1 d . . .
O1 O -0.48890(11) 1.05140(9) 0.09671(7) 0.0328(2) Uani 1 1 d . . .
O2 O -0.20046(11) 1.06615(9) 0.41676(8) 0.0345(2) Uani 1 1 d . . .
H1N H -0.305(2) 0.9282(16) 0.0153(14) 0.047(4) Uiso 1 1 d . . .
H2N H 0.061(2) 0.9222(16) 0.4558(14) 0.053(5) Uiso 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 C2 1.3878(15) . ?
C1 C6 1.3944(15) . ?
C1 H1 0.9500 . ?
C2 N1 1.3181(14) . ?
C2 C3 1.5251(15) . ?
C3 O1 1.2493(13) . ?
C3 C4 1.3958(15) . ?
C4 C5 1.3941(15) . ?
C4 H4 0.9500 . ?
C5 O2 1.2464(13) . ?
C5 C6 1.5302(15) . ?
C6 N2 1.3126(13) . ?
C7 N1 1.4620(14) . ?
C7 C8 1.5163(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5230(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5118(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3860(17) . ?
C10 C15 1.3914(17) . ?
C11 C12 1.3862(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3771(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3898(17) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 N2 1.4570(14) . ?
C16 C17 1.5157(17) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.5345(16) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5082(17) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.3809(19) . ?
C19 C24 1.3918(18) . ?
C20 C21 1.385(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
N1 H1N 0.898(17) . ?
N2 H2N 0.924(17) . ?

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 C6 118.67(10) . . ?
C2 C1 H1 120.7 . . ?
C6 C1 H1 120.7 . . ?
N1 C2 C1 124.34(10) . . ?
N1 C2 C3 114.40(9) . . ?
C1 C2 C3 121.25(10) . . ?
O1 C3 C4 125.60(10) . . ?
O1 C3 C2 116.37(10) . . ?
C4 C3 C2 118.03(9) . . ?
C5 C4 C3 122.80(10) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
O2 C5 C4 126.31(10) . . ?
O2 C5 C6 116.76(9) . . ?
C4 C5 C6 116.90(9) . . ?
N2 C6 C1 124.52(10) . . ?
N2 C6 C5 113.47(9) . . ?
C1 C6 C5 121.99(9) . . ?
N1 C7 C8 111.10(9) . . ?
N1 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C9 111.87(9) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 114.02(9) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C15 118.02(11) . . ?
C11 C10 C9 120.37(11) . . ?
C15 C10 C9 121.60(11) . . ?
C10 C11 C12 120.97(12) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 120.43(12) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.51(12) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.09(12) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 120.98(12) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
N2 C16 C17 111.81(10) . . ?
N2 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N2 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 C18 111.24(10) . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C17 112.89(9) . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 C24 118.30(12) . . ?
C20 C19 C18 121.03(11) . . ?
C24 C19 C18 120.67(12) . . ?
C19 C20 C21 121.40(14) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 119.57(16) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C23 C22 C21 119.71(15) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C24 C23 C22 120.25(15) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C19 120.75(14) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
C2 N1 C7 124.01(9) . . ?
C2 N1 H1N 116.7(10) . . ?
C7 N1 H1N 119.3(10) . . ?
C6 N2 C16 125.63(10) . . ?
C6 N2 H2N 118.1(10) . . ?
C16 N2 H2N 116.3(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 N1 -178.77(11) . . . . ?
C6 C1 C2 C3 0.20(17) . . . . ?
N1 C2 C3 O1 3.18(16) . . . . ?
C1 C2 C3 O1 -175.89(11) . . . . ?
N1 C2 C3 C4 -176.50(11) . . . . ?
C1 C2 C3 C4 4.43(17) . . . . ?
O1 C3 C4 C5 176.42(12) . . . . ?
C2 C3 C4 C5 -3.93(18) . . . . ?
C3 C4 C5 O2 -179.02(12) . . . . ?
C3 C4 C5 C6 -0.77(18) . . . . ?
C2 C1 C6 N2 173.04(11) . . . . ?
C2 C1 C6 C5 -5.22(17) . . . . ?
O2 C5 C6 N2 5.65(16) . . . . ?
C4 C5 C6 N2 -172.77(11) . . . . ?
O2 C5 C6 C1 -175.90(11) . . . . ?
C4 C5 C6 C1 5.68(17) . . . . ?
N1 C7 C8 C9 176.58(10) . . . . ?
C7 C8 C9 C10 178.39(11) . . . . ?
C8 C9 C10 C11 -135.48(13) . . . . ?
C8 C9 C10 C15 45.86(17) . . . . ?
C15 C10 C11 C12 -0.32(19) . . . . ?
C9 C10 C11 C12 -179.03(12) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 C10 -0.4(2) . . . . ?
C11 C10 C15 C14 0.57(19) . . . . ?
C9 C10 C15 C14 179.27(12) . . . . ?
N2 C16 C17 C18 -171.83(9) . . . . ?
C16 C17 C18 C19 65.13(14) . . . . ?
C17 C18 C19 C20 -114.81(13) . . . . ?
C17 C18 C19 C24 64.80(15) . . . . ?
C24 C19 C20 C21 -0.3(2) . . . . ?
C18 C19 C20 C21 179.28(13) . . . . ?
C19 C20 C21 C22 -0.7(2) . . . . ?
C20 C21 C22 C23 1.5(2) . . . . ?
C21 C22 C23 C24 -1.3(2) . . . . ?
C22 C23 C24 C19 0.3(2) . . . . ?
C20 C19 C24 C23 0.55(19) . . . . ?
C18 C19 C24 C23 -179.07(11) . . . . ?
C1 C2 N1 C7 -2.00(19) . . . . ?
C3 C2 N1 C7 178.96(10) . . . . ?
C8 C7 N1 C2 174.37(11) . . . . ?
C1 C6 N2 C16 -2.52(19) . . . . ?
C5 C6 N2 C16 175.88(11) . . . . ?
C17 C16 N2 C6 89.41(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
N1 H1N O1 0.898(17) 2.084(17) 2.9493(12) 161.4(14) 2_475
N2 H2N O2 0.924(17) 2.013(17) 2.7867(13) 140.2(14) 2_576

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.07
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_pblr11080316
_database_code_depnum_ccdc_archive 'CCDC 1531545'
_audit_update_record             
;
2017-02-07 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 N2 O2'
_chemical_formula_sum            'C24 H26 N2 O2'
_chemical_formula_weight         374.47
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21 '
_symmetry_space_group_name_Hall  'P 2yb '

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

_cell_length_a                   6.0492(4)
_cell_length_b                   13.9149(9)
_cell_length_c                   12.3077(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.355(4)
_cell_angle_gamma                90.00
_cell_volume                     1027.46(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5226
_cell_measurement_theta_min      4.82
_cell_measurement_theta_max      66.00

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7505
_exptl_absorpt_correction_T_max  0.9702
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Cu-ImuS microfocus tube'
_diffrn_radiation_monochromator  mirror
_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            6751
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.82
_diffrn_reflns_theta_max         66.35
_reflns_number_total             3057
_reflns_number_gt                2947
_reflns_threshold_expression     I>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)+(0.0659P)²+0.0872P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_number_reflns         3057
_refine_ls_number_parameters     263
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.033
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2360(3) 0.88035(12) 0.87876(14) 0.0271(4) Uani 1 1 d . . .
H1 H 0.3612 0.8784 0.8394 0.033 Uiso 1 1 calc R . .
C2 C 0.0992(3) 0.80031(13) 0.88171(13) 0.0253(4) Uani 1 1 d . . .
C3 C -0.1042(3) 0.80129(13) 0.94421(14) 0.0266(4) Uani 1 1 d . . .
C4 C -0.1367(3) 0.88291(13) 1.00548(14) 0.0277(4) Uani 1 1 d . . .
H4 H -0.2551 0.8830 1.0493 0.033 Uiso 1 1 calc R . .
C5 C -0.0030(3) 0.96476(13) 1.00545(13) 0.0253(4) Uani 1 1 d . . .
C6 C 0.1875(3) 0.96298(13) 0.93392(13) 0.0243(4) Uani 1 1 d . . .
C7 C 0.2930(3) 0.69862(13) 0.75822(15) 0.0314(4) Uani 1 1 d . . .
H7 H 0.4391 0.7252 0.7924 0.038 Uiso 1 1 calc R . .
C8 C 0.2274(5) 0.74949(15) 0.64814(18) 0.0472(6) Uani 1 1 d . . .
H8A H 0.0818 0.7243 0.6140 0.057 Uiso 1 1 calc R . .
H8B H 0.2093 0.8190 0.6615 0.057 Uiso 1 1 calc R . .
C9 C 0.3980(7) 0.73601(19) 0.5692(3) 0.0808(10) Uani 1 1 d . . .
H9A H 0.5445 0.7573 0.6041 0.121 Uiso 1 1 calc R . .
H9B H 0.3543 0.7741 0.5030 0.121 Uiso 1 1 calc R . .
H9C H 0.4053 0.6679 0.5497 0.121 Uiso 1 1 calc R . .
C10 C 0.3185(3) 0.59099(13) 0.74463(14) 0.0299(4) Uani 1 1 d . . .
C11 C 0.5219(3) 0.54709(15) 0.77809(14) 0.0343(4) Uani 1 1 d . . .
H11 H 0.6435 0.5843 0.8118 0.041 Uiso 1 1 calc R . .
C12 C 0.5487(4) 0.44945(15) 0.76268(17) 0.0400(5) Uani 1 1 d . . .
H12 H 0.6886 0.4201 0.7857 0.048 Uiso 1 1 calc R . .
C13 C 0.3733(4) 0.39449(14) 0.71397(16) 0.0392(5) Uani 1 1 d . . .
H13 H 0.3927 0.3276 0.7027 0.047 Uiso 1 1 calc R . .
C14 C 0.1691(4) 0.43741(15) 0.68162(16) 0.0390(5) Uani 1 1 d . . .
H14 H 0.0476 0.3998 0.6487 0.047 Uiso 1 1 calc R . .
C15 C 0.1413(3) 0.53506(14) 0.69714(15) 0.0340(4) Uani 1 1 d . . .
H15 H 0.0004 0.5640 0.6752 0.041 Uiso 1 1 calc R . .
C16 C 0.4837(3) 1.06479(12) 0.87227(14) 0.0262(4) Uani 1 1 d . . .
H16 H 0.6103 1.0228 0.9035 0.031 Uiso 1 1 calc R . .
C17 C 0.5534(3) 1.17000(13) 0.89242(15) 0.0304(4) Uani 1 1 d . . .
H17A H 0.4281 1.2123 0.8633 0.036 Uiso 1 1 calc R . .
H17B H 0.5850 1.1813 0.9723 0.036 Uiso 1 1 calc R . .
C18 C 0.7583(3) 1.19673(14) 0.83895(17) 0.0356(4) Uani 1 1 d . . .
H18A H 0.8803 1.1525 0.8639 0.053 Uiso 1 1 calc R . .
H18B H 0.8034 1.2626 0.8594 0.053 Uiso 1 1 calc R . .
H18C H 0.7230 1.1923 0.7591 0.053 Uiso 1 1 calc R . .
C19 C 0.4320(3) 1.04323(13) 0.75080(14) 0.0279(4) Uani 1 1 d . . .
C20 C 0.5903(3) 0.99753(14) 0.69641(17) 0.0357(4) Uani 1 1 d . . .
H20 H 0.7274 0.9776 0.7364 0.043 Uiso 1 1 calc R . .
C21 C 0.5506(4) 0.98082(15) 0.58510(18) 0.0449(5) Uani 1 1 d . . .
H21 H 0.6611 0.9502 0.5490 0.054 Uiso 1 1 calc R . .
C22 C 0.3530(4) 1.00812(18) 0.52631(18) 0.0475(6) Uani 1 1 d . . .
H22 H 0.3260 0.9965 0.4497 0.057 Uiso 1 1 calc R . .
C23 C 0.1931(4) 1.0527(2) 0.57941(17) 0.0480(5) Uani 1 1 d . . .
H23 H 0.0548 1.0707 0.5392 0.058 Uiso 1 1 calc R . .
C24 C 0.2327(3) 1.07123(16) 0.69043(16) 0.0371(4) Uani 1 1 d . . .
H24 H 0.1230 1.1033 0.7257 0.045 Uiso 1 1 calc R . .
N1 N 0.1252(3) 0.71824(11) 0.83186(12) 0.0277(3) Uani 1 1 d . . .
N2 N 0.2926(2) 1.04569(11) 0.93190(12) 0.0254(3) Uani 1 1 d . . .
O1 O -0.2232(2) 0.72780(9) 0.93548(11) 0.0347(3) Uani 1 1 d . . .
O2 O -0.0262(2) 1.04050(9) 1.05599(11) 0.0339(3) Uani 1 1 d . . .
H1N H 0.044(4) 0.6713(18) 0.8505(18) 0.033(5) Uiso 1 1 d . . .
H2N H 0.256(3) 1.0895(16) 0.9733(16) 0.019(5) Uiso 1 1 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 C6 1.386(3) . ?
C1 C2 1.391(3) . ?
C1 H1 0.9500 . ?
C2 N1 1.315(2) . ?
C2 C3 1.532(2) . ?
C3 O1 1.247(2) . ?
C3 C4 1.391(3) . ?
C4 C5 1.397(3) . ?
C4 H4 0.9500 . ?
C5 O2 1.241(2) . ?
C5 C6 1.537(2) . ?
C6 N2 1.317(2) . ?
C7 N1 1.470(2) . ?
C7 C10 1.517(3) . ?
C7 C8 1.535(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.516(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.388(3) . ?
C10 C15 1.391(3) . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 N2 1.471(2) . ?
C16 C19 1.518(2) . ?
C16 C17 1.535(2) . ?
C16 H16 1.0000 . ?
C17 C18 1.522(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C24 1.388(3) . ?
C19 C20 1.391(3) . ?
C20 C21 1.380(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.370(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
N1 H1N 0.86(3) . ?
N2 H2N 0.84(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
C6 C1 C2 119.17(15) . . ?
C6 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
N1 C2 C1 125.15(16) . . ?
N1 C2 C3 113.20(15) . . ?
C1 C2 C3 121.65(15) . . ?
O1 C3 C4 126.58(16) . . ?
O1 C3 C2 116.17(15) . . ?
C4 C3 C2 117.25(15) . . ?
C3 C4 C5 122.90(15) . . ?
C3 C4 H4 118.5 . . ?
C5 C4 H4 118.5 . . ?
O2 C5 C4 126.11(16) . . ?
O2 C5 C6 116.24(16) . . ?
C4 C5 C6 117.62(15) . . ?
N2 C6 C1 125.64(15) . . ?
N2 C6 C5 113.33(15) . . ?
C1 C6 C5 121.03(15) . . ?
N1 C7 C10 109.84(15) . . ?
N1 C7 C8 109.75(16) . . ?
C10 C7 C8 112.11(16) . . ?
N1 C7 H7 108.4 . . ?
C10 C7 H7 108.4 . . ?
C8 C7 H7 108.4 . . ?
C9 C8 C7 112.8(2) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 118.97(18) . . ?
C11 C10 C7 120.04(17) . . ?
C15 C10 C7 120.98(18) . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.59(19) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 120.41(19) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
N2 C16 C19 112.31(14) . . ?
N2 C16 C17 107.99(14) . . ?
C19 C16 C17 111.44(14) . . ?
N2 C16 H16 108.3 . . ?
C19 C16 H16 108.3 . . ?
C17 C16 H16 108.3 . . ?
C18 C17 C16 112.66(15) . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 118.35(17) . . ?
C24 C19 C16 121.82(16) . . ?
C20 C19 C16 119.78(17) . . ?
C21 C20 C19 120.8(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 120.46(19) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.41(19) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C24 C23 C22 120.6(2) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C19 120.39(19) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C2 N1 C7 125.61(16) . . ?
C2 N1 H1N 115.2(15) . . ?
C7 N1 H1N 118.9(15) . . ?
C6 N2 C16 125.44(16) . . ?
C6 N2 H2N 117.0(13) . . ?
C16 N2 H2N 117.2(13) . . ?

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 N1 179.08(17) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
N1 C2 C3 O1 -3.5(2) . . . . ?
C1 C2 C3 O1 175.52(16) . . . . ?
N1 C2 C3 C4 175.85(16) . . . . ?
C1 C2 C3 C4 -5.1(2) . . . . ?
O1 C3 C4 C5 -175.92(17) . . . . ?
C2 C3 C4 C5 4.8(2) . . . . ?
C3 C4 C5 O2 178.17(17) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C2 C1 C6 N2 -174.99(16) . . . . ?
C2 C1 C6 C5 5.0(3) . . . . ?
O2 C5 C6 N2 -3.6(2) . . . . ?
C4 C5 C6 N2 174.69(15) . . . . ?
O2 C5 C6 C1 176.42(16) . . . . ?
C4 C5 C6 C1 -5.3(2) . . . . ?
N1 C7 C8 C9 177.6(2) . . . . ?
C10 C7 C8 C9 -60.1(3) . . . . ?
N1 C7 C10 C11 -118.17(18) . . . . ?
C8 C7 C10 C11 119.5(2) . . . . ?
N1 C7 C10 C15 62.9(2) . . . . ?
C8 C7 C10 C15 -59.4(2) . . . . ?
C15 C10 C11 C12 1.1(3) . . . . ?
C7 C10 C11 C12 -177.85(18) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C10 0.4(3) . . . . ?
C11 C10 C15 C14 -1.2(3) . . . . ?
C7 C10 C15 C14 177.68(17) . . . . ?
N2 C16 C17 C18 177.16(15) . . . . ?
C19 C16 C17 C18 -59.0(2) . . . . ?
N2 C16 C19 C24 43.9(2) . . . . ?
C17 C16 C19 C24 -77.4(2) . . . . ?
N2 C16 C19 C20 -138.66(17) . . . . ?
C17 C16 C19 C20 100.02(19) . . . . ?
C24 C19 C20 C21 0.3(3) . . . . ?
C16 C19 C20 C21 -177.26(17) . . . . ?
C19 C20 C21 C22 -0.7(3) . . . . ?
C20 C21 C22 C23 0.0(3) . . . . ?
C21 C22 C23 C24 1.1(4) . . . . ?
C22 C23 C24 C19 -1.6(3) . . . . ?
C20 C19 C24 C23 0.9(3) . . . . ?
C16 C19 C24 C23 178.33(19) . . . . ?
C1 C2 N1 C7 -4.6(3) . . . . ?
C3 C2 N1 C7 174.45(16) . . . . ?
C10 C7 N1 C2 162.88(17) . . . . ?
C8 C7 N1 C2 -73.4(2) . . . . ?
C1 C6 N2 C16 -1.2(3) . . . . ?
C5 C6 N2 C16 178.81(14) . . . . ?
C19 C16 N2 C6 56.7(2) . . . . ?
C17 C16 N2 C6 180.00(16) . . . . ?

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
N1 H1N O2 0.86(3) 2.16(3) 2.931(2) 147.7(19) 2_547
N2 H2N O1 0.84(2) 2.25(2) 3.072(2) 165.3(17) 2_557

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        66.35
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_pblr110509
_database_code_depnum_ccdc_archive 'CCDC 1531550'
_audit_update_record             
;
2017-02-07 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H34 N2 O2'
_chemical_formula_sum            'C36 H34 N2 O2'
_chemical_formula_weight         526.65

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc '

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

_cell_length_a                   8.284(9)
_cell_length_b                   30.84(3)
_cell_length_c                   11.178(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.85(3)
_cell_angle_gamma                90.00
_cell_volume                     2822(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2444
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      25.83

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  triumph
_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            16427
_diffrn_reflns_av_R_equivalents  0.1031
_diffrn_reflns_av_sigmaI/netI    0.1424
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         29.02
_reflns_number_total             6552
_reflns_number_gt                2632
_reflns_threshold_expression     I>2sigma(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 > 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)+(0.1121P)²+0.0000P] 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         6552
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2266
_refine_ls_R_factor_gt           0.0996
_refine_ls_wR_factor_ref         0.2609
_refine_ls_wR_factor_gt          0.2065
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0774(4) 0.96754(12) 0.1401(4) 0.0388(9) Uani 1 1 d . . .
H1 H 1.0022 0.9485 0.0936 0.047 Uiso 1 1 calc R . .
C2 C 1.0458(4) 0.98318(11) 0.2506(4) 0.0361(9) Uani 1 1 d . . .
C3 C 1.1595(5) 1.01514(13) 0.3232(4) 0.0464(10) Uani 1 1 d . . .
C4 C 1.3008(5) 1.02779(12) 0.2766(4) 0.0470(11) Uani 1 1 d . . .
H4 H 1.3715 1.0486 0.3201 0.056 Uiso 1 1 calc R . .
C5 C 1.3409(4) 1.01134(12) 0.1707(4) 0.0421(10) Uani 1 1 d . . .
C6 C 1.2198(4) 0.97989(11) 0.0982(4) 0.0374(9) Uani 1 1 d . . .
C7 C 0.7940(4) 0.94016(13) 0.2488(4) 0.0453(10) Uani 1 1 d . . .
H7A H 0.8461 0.9115 0.2423 0.054 Uiso 1 1 calc R . .
H7B H 0.7447 0.9494 0.1664 0.054 Uiso 1 1 calc R . .
C8 C 0.6613(4) 0.93626(12) 0.3283(4) 0.0424(10) Uani 1 1 d . . .
H8A H 0.5998 0.9639 0.3252 0.051 Uiso 1 1 calc R . .
H8B H 0.7132 0.9316 0.4132 0.051 Uiso 1 1 calc R . .
C9 C 0.5413(4) 0.89905(12) 0.2900(4) 0.0419(10) Uani 1 1 d . . .
H9 H 0.4954 0.9037 0.2028 0.050 Uiso 1 1 calc R . .
C10 C 0.3966(5) 0.89845(13) 0.3611(4) 0.0465(11) Uani 1 1 d . . .
C11 C 0.3876(5) 0.92565(15) 0.4581(5) 0.0617(13) Uani 1 1 d . . .
H11 H 0.4713 0.9464 0.4816 0.074 Uiso 1 1 calc R . .
C12 C 0.2549(6) 0.92268(17) 0.5219(5) 0.0779(17) Uani 1 1 d . . .
H12 H 0.2505 0.9408 0.5901 0.093 Uiso 1 1 calc R . .
C13 C 0.1313(6) 0.8936(2) 0.4859(7) 0.086(2) Uani 1 1 d . . .
H13 H 0.0398 0.8923 0.5276 0.103 Uiso 1 1 calc R . .
C14 C 0.1397(6) 0.86644(18) 0.3899(6) 0.0824(18) Uani 1 1 d . . .
H14 H 0.0553 0.8459 0.3664 0.099 Uiso 1 1 calc R . .
C15 C 0.2699(5) 0.86894(15) 0.3277(5) 0.0631(13) Uani 1 1 d . . .
H15 H 0.2740 0.8502 0.2607 0.076 Uiso 1 1 calc R . .
C16 C 0.6234(5) 0.85478(13) 0.2996(4) 0.0438(10) Uani 1 1 d . . .
C17 C 0.7135(5) 0.84083(14) 0.4076(4) 0.0523(11) Uani 1 1 d . . .
H17 H 0.7277 0.8600 0.4749 0.063 Uiso 1 1 calc R . .
C18 C 0.7832(6) 0.80027(16) 0.4210(5) 0.0686(14) Uani 1 1 d . . .
H18 H 0.8430 0.7916 0.4966 0.082 Uiso 1 1 calc R . .
C19 C 0.7652(7) 0.77251(18) 0.3238(7) 0.0823(17) Uani 1 1 d . . .
H19 H 0.8155 0.7448 0.3313 0.099 Uiso 1 1 calc R . .
C20 C 0.6758(9) 0.78462(19) 0.2171(6) 0.0930(19) Uani 1 1 d . . .
H20 H 0.6605 0.7649 0.1510 0.112 Uiso 1 1 calc R . .
C21 C 0.6060(7) 0.82585(17) 0.2036(5) 0.0753(15) Uani 1 1 d . . .
H21 H 0.5459 0.8342 0.1278 0.090 Uiso 1 1 calc R . .
C22 C 1.1795(5) 0.93335(12) -0.0826(4) 0.0436(10) Uani 1 1 d . . .
H22A H 1.2185 0.9344 -0.1619 0.052 Uiso 1 1 calc R . .
H22B H 1.0613 0.9401 -0.0960 0.052 Uiso 1 1 calc R . .
C23 C 1.2062(5) 0.88777(12) -0.0293(4) 0.0446(10) Uani 1 1 d . . .
H23A H 1.1690 0.8873 0.0507 0.054 Uiso 1 1 calc R . .
H23B H 1.3248 0.8815 -0.0161 0.054 Uiso 1 1 calc R . .
C24 C 1.1172(5) 0.85126(12) -0.1083(4) 0.0442(10) Uani 1 1 d . . .
H24 H 1.1597 0.8518 -0.1873 0.053 Uiso 1 1 calc R . .
C25 C 1.1667(5) 0.80750(13) -0.0488(4) 0.0503(11) Uani 1 1 d . . .
C26 C 1.2877(6) 0.78250(15) -0.0890(5) 0.0671(14) Uani 1 1 d . . .
H26 H 1.3378 0.7924 -0.1549 0.081 Uiso 1 1 calc R . .
C27 C 1.3359(8) 0.74324(18) -0.0339(6) 0.0849(17) Uani 1 1 d . . .
H27 H 1.4172 0.7262 -0.0630 0.102 Uiso 1 1 calc R . .
C28 C 1.2660(8) 0.72902(18) 0.0626(7) 0.0888(18) Uani 1 1 d . . .
H28 H 1.2990 0.7022 0.1004 0.107 Uiso 1 1 calc R . .
C29 C 1.1498(7) 0.75334(17) 0.1042(5) 0.0780(16) Uani 1 1 d . . .
H29 H 1.1031 0.7436 0.1718 0.094 Uiso 1 1 calc R . .
C30 C 1.0984(6) 0.79225(15) 0.0491(5) 0.0624(13) Uani 1 1 d . . .
H30 H 1.0158 0.8087 0.0786 0.075 Uiso 1 1 calc R . .
C31 C 0.9309(5) 0.85724(13) -0.1373(4) 0.0456(10) Uani 1 1 d . . .
C32 C 0.8405(5) 0.87330(15) -0.0523(5) 0.0585(12) Uani 1 1 d . . .
H32 H 0.8945 0.8809 0.0260 0.070 Uiso 1 1 calc R . .
C33 C 0.6731(6) 0.87833(16) -0.0800(5) 0.0683(14) Uani 1 1 d . . .
H33 H 0.6141 0.8903 -0.0215 0.082 Uiso 1 1 calc R . .
C34 C 0.5903(6) 0.86604(17) -0.1926(5) 0.0707(15) Uani 1 1 d . . .
H34 H 0.4753 0.8696 -0.2117 0.085 Uiso 1 1 calc R . .
C35 C 0.6771(6) 0.84883(16) -0.2751(5) 0.0716(15) Uani 1 1 d . . .
H35 H 0.6216 0.8394 -0.3514 0.086 Uiso 1 1 calc R . .
C36 C 0.8468(6) 0.84482(14) -0.2490(4) 0.0567(12) Uani 1 1 d . . .
H36 H 0.9055 0.8334 -0.3086 0.068 Uiso 1 1 calc R . .
N1 N 0.9179(4) 0.97180(10) 0.2999(3) 0.0427(8) Uani 1 1 d . . .
H1A H 0.9058 0.9841 0.3690 0.051 Uiso 1 1 calc R . .
N2 N 1.2660(3) 0.96547(9) -0.0023(3) 0.0382(8) Uani 1 1 d . . .
H2 H 1.3566 0.9762 -0.0223 0.046 Uiso 1 1 calc R . .
O1 O 1.1175(4) 1.02841(10) 0.4195(3) 0.0664(10) Uani 1 1 d . . .
O2 O 1.4677(3) 1.02001(9) 0.1269(3) 0.0593(9) 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 C2 1.387(5) . ?
C1 C6 1.389(5) . ?
C1 H1 0.9500 . ?
C2 N1 1.315(4) . ?
C2 C3 1.511(6) . ?
C3 O1 1.250(5) . ?
C3 C4 1.408(5) . ?
C4 C5 1.374(5) . ?
C4 H4 0.9500 . ?
C5 O2 1.254(4) . ?
C5 C6 1.534(5) . ?
C6 N2 1.319(5) . ?
C7 N1 1.467(5) . ?
C7 C8 1.521(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.535(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C16 1.522(6) . ?
C9 C10 1.537(5) . ?
C9 H9 1.0000 . ?
C10 C11 1.382(6) . ?
C10 C15 1.396(6) . ?
C11 C12 1.402(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.372(6) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.386(6) . ?
C16 C17 1.387(6) . ?
C17 C18 1.376(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.374(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.356(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(8) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 N2 1.450(5) . ?
C22 C23 1.529(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.546(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.532(6) . ?
C24 C31 1.538(6) . ?
C24 H24 1.0000 . ?
C25 C30 1.389(6) . ?
C25 C26 1.393(6) . ?
C26 C27 1.389(7) . ?
C26 H26 0.9500 . ?
C27 C28 1.372(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.358(8) . ?
C28 H28 0.9500 . ?
C29 C30 1.385(7) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C36 1.387(6) . ?
C31 C32 1.388(6) . ?
C32 C33 1.382(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.390(7) . ?
C33 H33 0.9500 . ?
C34 C35 1.361(7) . ?
C34 H34 0.9500 . ?
C35 C36 1.397(7) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
N1 H1A 0.8800 . ?
N2 H2 0.8800 . ?

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 C6 119.5(4) . . ?
C2 C1 H1 120.3 . . ?
C6 C1 H1 120.3 . . ?
N1 C2 C1 123.7(3) . . ?
N1 C2 C3 115.1(3) . . ?
C1 C2 C3 121.2(3) . . ?
O1 C3 C4 125.8(4) . . ?
O1 C3 C2 116.3(3) . . ?
C4 C3 C2 117.8(4) . . ?
C5 C4 C3 122.8(4) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
O2 C5 C4 125.8(4) . . ?
O2 C5 C6 116.5(3) . . ?
C4 C5 C6 117.6(3) . . ?
N2 C6 C1 124.6(4) . . ?
N2 C6 C5 114.3(3) . . ?
C1 C6 C5 121.0(3) . . ?
N1 C7 C8 110.5(3) . . ?
N1 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C9 113.0(3) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C16 C9 C8 112.8(3) . . ?
C16 C9 C10 109.1(3) . . ?
C8 C9 C10 112.8(3) . . ?
C16 C9 H9 107.3 . . ?
C8 C9 H9 107.3 . . ?
C10 C9 H9 107.3 . . ?
C11 C10 C15 118.5(4) . . ?
C11 C10 C9 122.6(4) . . ?
C15 C10 C9 118.9(4) . . ?
C10 C11 C12 120.0(5) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.0(5) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.0(5) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 121.2(5) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C21 C16 C17 116.9(4) . . ?
C21 C16 C9 122.1(4) . . ?
C17 C16 C9 121.0(4) . . ?
C18 C17 C16 122.5(5) . . ?
C18 C17 H17 118.7 . . ?
C16 C17 H17 118.7 . . ?
C19 C18 C17 119.2(5) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C20 C19 C18 120.2(5) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.5(5) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 120.8(5) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
N2 C22 C23 111.0(3) . . ?
N2 C22 H22A 109.4 . . ?
C23 C22 H22A 109.4 . . ?
N2 C22 H22B 109.4 . . ?
C23 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 C24 114.8(4) . . ?
C22 C23 H23A 108.6 . . ?
C24 C23 H23A 108.6 . . ?
C22 C23 H23B 108.6 . . ?
C24 C23 H23B 108.6 . . ?
H23A C23 H23B 107.5 . . ?
C25 C24 C31 113.0(3) . . ?
C25 C24 C23 108.7(4) . . ?
C31 C24 C23 114.1(3) . . ?
C25 C24 H24 106.9 . . ?
C31 C24 H24 106.9 . . ?
C23 C24 H24 106.9 . . ?
C30 C25 C26 117.9(4) . . ?
C30 C25 C24 121.7(4) . . ?
C26 C25 C24 120.3(4) . . ?
C27 C26 C25 120.7(5) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C28 C27 C26 120.0(5) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C29 C28 C27 120.0(5) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.8(5) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C29 C30 C25 120.6(5) . . ?
C29 C30 H30 119.7 . . ?
C25 C30 H30 119.7 . . ?
C36 C31 C32 117.7(4) . . ?
C36 C31 C24 120.4(4) . . ?
C32 C31 C24 121.9(4) . . ?
C33 C32 C31 121.0(5) . . ?
C33 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
C32 C33 C34 120.7(5) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C35 C34 C33 118.7(5) . . ?
C35 C34 H34 120.6 . . ?
C33 C34 H34 120.6 . . ?
C34 C35 C36 120.8(5) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 H35 119.6 . . ?
C31 C36 C35 120.9(4) . . ?
C31 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C2 N1 C7 125.1(3) . . ?
C2 N1 H1A 117.4 . . ?
C7 N1 H1A 117.4 . . ?
C6 N2 C22 125.2(3) . . ?
C6 N2 H2 117.4 . . ?
C22 N2 H2 117.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_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 N1 -176.9(4) . . . . ?
C6 C1 C2 C3 3.0(6) . . . . ?
N1 C2 C3 O1 -2.4(6) . . . . ?
C1 C2 C3 O1 177.7(4) . . . . ?
N1 C2 C3 C4 178.5(4) . . . . ?
C1 C2 C3 C4 -1.5(6) . . . . ?
O1 C3 C4 C5 178.9(4) . . . . ?
C2 C3 C4 C5 -2.0(6) . . . . ?
C3 C4 C5 O2 -177.1(4) . . . . ?
C3 C4 C5 C6 3.6(6) . . . . ?
C2 C1 C6 N2 176.6(3) . . . . ?
C2 C1 C6 C5 -1.3(6) . . . . ?
O2 C5 C6 N2 0.5(5) . . . . ?
C4 C5 C6 N2 179.9(3) . . . . ?
O2 C5 C6 C1 178.7(4) . . . . ?
C4 C5 C6 C1 -1.9(6) . . . . ?
N1 C7 C8 C9 -171.7(3) . . . . ?
C7 C8 C9 C16 62.3(5) . . . . ?
C7 C8 C9 C10 -173.5(3) . . . . ?
C16 C9 C10 C11 119.3(4) . . . . ?
C8 C9 C10 C11 -6.9(6) . . . . ?
C16 C9 C10 C15 -59.9(5) . . . . ?
C8 C9 C10 C15 173.9(4) . . . . ?
C15 C10 C11 C12 1.2(7) . . . . ?
C9 C10 C11 C12 -178.0(4) . . . . ?
C10 C11 C12 C13 -1.9(8) . . . . ?
C11 C12 C13 C14 2.0(9) . . . . ?
C12 C13 C14 C15 -1.5(9) . . . . ?
C13 C14 C15 C10 0.8(8) . . . . ?
C11 C10 C15 C14 -0.6(7) . . . . ?
C9 C10 C15 C14 178.6(4) . . . . ?
C8 C9 C16 C21 -127.6(4) . . . . ?
C10 C9 C16 C21 106.1(5) . . . . ?
C8 C9 C16 C17 55.3(5) . . . . ?
C10 C9 C16 C17 -70.9(4) . . . . ?
C21 C16 C17 C18 -0.2(6) . . . . ?
C9 C16 C17 C18 177.0(4) . . . . ?
C16 C17 C18 C19 0.9(7) . . . . ?
C17 C18 C19 C20 -1.9(8) . . . . ?
C18 C19 C20 C21 2.2(9) . . . . ?
C17 C16 C21 C20 0.5(7) . . . . ?
C9 C16 C21 C20 -176.7(4) . . . . ?
C19 C20 C21 C16 -1.5(9) . . . . ?
N2 C22 C23 C24 179.5(3) . . . . ?
C22 C23 C24 C25 175.3(3) . . . . ?
C22 C23 C24 C31 -57.7(4) . . . . ?
C31 C24 C25 C30 -48.8(5) . . . . ?
C23 C24 C25 C30 78.9(5) . . . . ?
C31 C24 C25 C26 133.8(4) . . . . ?
C23 C24 C25 C26 -98.6(5) . . . . ?
C30 C25 C26 C27 1.1(7) . . . . ?
C24 C25 C26 C27 178.6(5) . . . . ?
C25 C26 C27 C28 -1.1(8) . . . . ?
C26 C27 C28 C29 0.0(9) . . . . ?
C27 C28 C29 C30 1.0(9) . . . . ?
C28 C29 C30 C25 -1.0(8) . . . . ?
C26 C25 C30 C29 -0.1(7) . . . . ?
C24 C25 C30 C29 -177.6(4) . . . . ?
C25 C24 C31 C36 -91.0(5) . . . . ?
C23 C24 C31 C36 144.1(4) . . . . ?
C25 C24 C31 C32 86.2(5) . . . . ?
C23 C24 C31 C32 -38.7(5) . . . . ?
C36 C31 C32 C33 -2.5(6) . . . . ?
C24 C31 C32 C33 -179.8(4) . . . . ?
C31 C32 C33 C34 2.2(7) . . . . ?
C32 C33 C34 C35 0.2(8) . . . . ?
C33 C34 C35 C36 -2.1(7) . . . . ?
C32 C31 C36 C35 0.7(6) . . . . ?
C24 C31 C36 C35 178.0(4) . . . . ?
C34 C35 C36 C31 1.6(7) . . . . ?
C1 C2 N1 C7 2.2(6) . . . . ?
C3 C2 N1 C7 -177.7(4) . . . . ?
C8 C7 N1 C2 -178.2(4) . . . . ?
C1 C6 N2 C22 -2.5(6) . . . . ?
C5 C6 N2 C22 175.6(3) . . . . ?
C23 C22 N2 C6 -75.9(4) . . . . ?

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
N1 H1A O1 0.88 2.43 3.194(6) 145.2 3_776
N2 H2 O2 0.88 2.01 2.820(4) 153.3 3_875

_diffrn_measured_fraction_theta_max 0.871
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_pblr110804
_database_code_depnum_ccdc_archive 'CCDC 1531549'
_audit_update_record             
;
2017-02-07 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H30 N2 O2, H2 O'
_chemical_formula_sum            'C26 H32 N2 O3'
_chemical_formula_weight         420.54

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                   9.1007(11)
_cell_length_b                   9.4113(11)
_cell_length_c                   15.0880(18)
_cell_angle_alpha                97.591(3)
_cell_angle_beta                 90.128(3)
_cell_angle_gamma                116.126(2)
_cell_volume                     1147.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2204
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      26.04

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9689
_exptl_absorpt_correction_T_max  0.9984
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  triumph
_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            12917
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0798
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         28.12
_reflns_number_total             5574
_reflns_number_gt                2895
_reflns_threshold_expression     I>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)+(0.0818P)²+0.2407P] 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         5574
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1440
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.1845
_refine_ls_wR_factor_gt          0.1538
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 1.0688(3) 0.4867(3) 0.38146(15) 0.0292(5) Uani 1 1 d . . .
H1 H 0.9963 0.3959 0.3410 0.035 Uiso 1 1 calc R . .
C2 C 1.2161(3) 0.4964(3) 0.41410(15) 0.0287(5) Uani 1 1 d . . .
C3 C 1.3378(3) 0.6450(3) 0.47538(16) 0.0313(5) Uani 1 1 d . . .
C4 C 1.2955(3) 0.7680(3) 0.50026(17) 0.0337(6) Uani 1 1 d . . .
H4 H 1.3711 0.8611 0.5381 0.040 Uiso 1 1 calc R . .
C5 C 1.1455(3) 0.7604(3) 0.47175(16) 0.0305(5) Uani 1 1 d . . .
C6 C 1.0284(3) 0.6114(3) 0.40869(15) 0.0276(5) Uani 1 1 d . . .
C7 C 1.1685(3) 0.2332(3) 0.33695(18) 0.0361(6) Uani 1 1 d . . .
H7A H 1.1445 0.2573 0.2782 0.043 Uiso 1 1 calc R . .
H7B H 1.0626 0.1741 0.3630 0.043 Uiso 1 1 calc R . .
C8 C 1.2552(3) 0.1278(3) 0.32256(17) 0.0343(6) Uani 1 1 d . . .
H8A H 1.2631 0.0881 0.3791 0.041 Uiso 1 1 calc R . .
H8B H 1.3679 0.1908 0.3050 0.041 Uiso 1 1 calc R . .
C9 C 1.1618(3) -0.0131(3) 0.24970(18) 0.0397(6) Uani 1 1 d . . .
H9A H 1.1622 0.0279 0.1925 0.048 Uiso 1 1 calc R . .
H9B H 1.0462 -0.0683 0.2650 0.048 Uiso 1 1 calc R . .
C10 C 1.2318(3) -0.1344(3) 0.23619(19) 0.0420(7) Uani 1 1 d . . .
H10A H 1.2206 -0.1836 0.2914 0.050 Uiso 1 1 calc R . .
H10B H 1.1656 -0.2205 0.1870 0.050 Uiso 1 1 calc R . .
C11 C 1.4092(3) -0.0644(3) 0.21444(17) 0.0360(6) Uani 1 1 d . . .
C12 C 1.4590(4) 0.0027(4) 0.13741(19) 0.0560(8) Uani 1 1 d . . .
H12 H 1.3797 0.0023 0.0962 0.067 Uiso 1 1 calc R . .
C13 C 1.6228(4) 0.0705(5) 0.1191(2) 0.0659(9) Uani 1 1 d . . .
H13 H 1.6545 0.1161 0.0656 0.079 Uiso 1 1 calc R . .
C14 C 1.7396(4) 0.0725(4) 0.1774(2) 0.0551(8) Uani 1 1 d . . .
H14 H 1.8521 0.1204 0.1650 0.066 Uiso 1 1 calc R . .
C15 C 1.6926(3) 0.0050(4) 0.2537(2) 0.0549(8) Uani 1 1 d . . .
H15 H 1.7724 0.0045 0.2942 0.066 Uiso 1 1 calc R . .
C16 C 1.5295(3) -0.0626(3) 0.27183(19) 0.0465(7) Uani 1 1 d . . .
H16 H 1.4986 -0.1091 0.3251 0.056 Uiso 1 1 calc R . .
C17 C 0.7564(3) 0.4990(3) 0.32540(18) 0.0398(6) Uani 1 1 d . . .
H17A H 0.6523 0.4984 0.3449 0.048 Uiso 1 1 calc R A 1
H17B H 0.7485 0.3909 0.3264 0.048 Uiso 1 1 calc R A 1
C18 C 0.7841(8) 0.5419(10) 0.2281(5) 0.0468(7) Uani 0.50 1 d P B 1
H18A H 0.8185 0.6579 0.2303 0.056 Uiso 0.50 1 calc PR B 1
H18B H 0.8743 0.5194 0.2044 0.056 Uiso 0.50 1 calc PR B 1
C19 C 0.6306(7) 0.4482(7) 0.1640(4) 0.0468(7) Uani 0.50 1 d P B 1
H19A H 0.5850 0.3332 0.1697 0.056 Uiso 0.50 1 calc PR B 1
H19B H 0.6618 0.4601 0.1016 0.056 Uiso 0.50 1 calc PR B 1
C20 C 0.4947(7) 0.5061(7) 0.1830(4) 0.0468(7) Uani 0.50 1 d P B 1
H20A H 0.4669 0.4967 0.2460 0.056 Uiso 0.50 1 calc PR B 1
H20B H 0.5416 0.6210 0.1768 0.056 Uiso 0.50 1 calc PR B 1
C21 C 0.3397(8) 0.4191(9) 0.1243(5) 0.0585(5) Uani 0.50 1 d P B 1
C22 C 0.2181(9) 0.4676(11) 0.1279(6) 0.0585(5) Uani 0.50 1 d P B 1
H22 H 0.2287 0.5530 0.1729 0.070 Uiso 0.50 1 calc PR B 1
C25 C 0.1649(9) 0.2049(10) 0.0068(5) 0.0585(5) Uani 0.50 1 d P B 1
H25 H 0.1446 0.1095 -0.0323 0.070 Uiso 0.50 1 calc PR B 1
C26 C 0.3083(8) 0.2819(8) 0.0619(5) 0.0585(5) Uani 0.50 1 d P B 1
H26 H 0.3872 0.2412 0.0575 0.070 Uiso 0.50 1 calc PR B 1
C18B C 0.7406(8) 0.5596(9) 0.2427(5) 0.0468(7) Uani 0.50 1 d P B 2
H18C H 0.8182 0.5480 0.1999 0.056 Uiso 0.50 1 calc PR B 2
H18D H 0.7681 0.6747 0.2566 0.056 Uiso 0.50 1 calc PR B 2
C19B C 0.5619(7) 0.4644(7) 0.1998(4) 0.0468(7) Uani 0.50 1 d P B 2
H19C H 0.5333 0.3489 0.1896 0.056 Uiso 0.50 1 calc PR B 2
H19D H 0.4856 0.4802 0.2423 0.056 Uiso 0.50 1 calc PR B 2
C20B C 0.5396(6) 0.5141(7) 0.1144(4) 0.0468(7) Uani 0.50 1 d P B 2
H20C H 0.6088 0.4905 0.0700 0.056 Uiso 0.50 1 calc PR B 2
H20D H 0.5750 0.6310 0.1234 0.056 Uiso 0.50 1 calc PR B 2
C21B C 0.3638(8) 0.4281(9) 0.0794(5) 0.0585(5) Uani 0.50 1 d P B 2
C22B C 0.2497(9) 0.4828(11) 0.1061(6) 0.0585(5) Uani 0.50 1 d P B 2
H22B H 0.2823 0.5768 0.1488 0.070 Uiso 0.50 1 calc PR B 2
C25B C 0.1549(10) 0.2188(10) -0.0220(5) 0.0585(5) Uani 0.50 1 d P B 2
H25B H 0.1218 0.1297 -0.0682 0.070 Uiso 0.50 1 calc PR B 2
C26B C 0.3152(8) 0.2957(8) 0.0124(5) 0.0585(5) Uani 0.50 1 d P B 2
H26B H 0.3923 0.2592 -0.0093 0.070 Uiso 0.50 1 calc PR B 2
C23 C 0.0831(4) 0.3985(4) 0.0700(2) 0.0585(5) Uani 1 1 d . . .
H23 H 0.0088 0.4448 0.0728 0.070 Uiso 1 1 calc R B 1
C24 C 0.0477(4) 0.2671(4) 0.0083(2) 0.0585(5) Uani 1 1 d . B .
H24 H -0.0485 0.2200 -0.0311 0.070 Uiso 1 1 calc R C 1
N1 N 1.2644(2) 0.3833(2) 0.39601(14) 0.0310(5) Uani 1 1 d . . .
N2 N 0.8922(2) 0.6161(2) 0.38608(14) 0.0319(5) Uani 1 1 d . B .
O1 O 1.47037(19) 0.6442(2) 0.49810(13) 0.0439(5) Uani 1 1 d . . .
O2 O 1.0979(2) 0.8650(2) 0.49218(13) 0.0431(5) Uani 1 1 d . . .
O3 O 0.7523(3) 0.8271(3) 0.41791(14) 0.0449(5) Uani 1 1 d . . .
H1N H 1.360(3) 0.399(3) 0.4230(17) 0.038(7) Uiso 1 1 d . . .
H2N H 0.883(3) 0.701(3) 0.4095(18) 0.043(8) Uiso 1 1 d . . .
H1W H 0.657(5) 0.780(4) 0.443(2) 0.077(12) Uiso 1 1 d . . .
H2W H 0.794(4) 0.922(4) 0.448(2) 0.071(11) Uiso 1 1 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 1.387(3) . ?
C1 C6 1.391(3) . ?
C1 H1 0.9500 . ?
C2 N1 1.318(3) . ?
C2 C3 1.525(3) . ?
C3 O1 1.258(3) . ?
C3 C4 1.380(3) . ?
C4 C5 1.399(3) . ?
C4 H4 0.9500 . ?
C5 O2 1.245(3) . ?
C5 C6 1.528(3) . ?
C6 N2 1.306(3) . ?
C7 N1 1.459(3) . ?
C7 C8 1.512(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.519(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.527(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.507(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.378(4) . ?
C11 C16 1.387(4) . ?
C12 C13 1.384(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.371(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.366(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N2 1.452(3) . ?
C17 C18B 1.470(8) . ?
C17 C18 1.566(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.532(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.569(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.493(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.369(11) . ?
C21 C26 1.410(10) . ?
C22 C23 1.355(9) . ?
C22 H22 0.9500 . ?
C25 C26 1.386(9) . ?
C25 C24 1.424(9) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C18B C19B 1.557(8) . ?
C18B H18C 0.9900 . ?
C18B H18D 0.9900 . ?
C19B C20B 1.471(8) . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C20B C21B 1.496(8) . ?
C20B H20C 0.9900 . ?
C20B H20D 0.9900 . ?
C21B C22B 1.387(10) . ?
C21B C26B 1.397(10) . ?
C22B C23 1.431(9) . ?
C22B H22B 0.9500 . ?
C25B C24 1.306(9) . ?
C25B C26B 1.374(9) . ?
C25B H25B 0.9500 . ?
C26B H26B 0.9500 . ?
C23 C24 1.358(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
N1 H1N 0.90(3) . ?
N2 H2N 0.87(3) . ?
O3 H1W 0.89(4) . ?
O3 H2W 0.86(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
C2 C1 C6 119.3(2) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
N1 C2 C1 124.7(2) . . ?
N1 C2 C3 114.23(19) . . ?
C1 C2 C3 121.1(2) . . ?
O1 C3 C4 125.7(2) . . ?
O1 C3 C2 115.9(2) . . ?
C4 C3 C2 118.38(19) . . ?
C3 C4 C5 122.4(2) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
O2 C5 C4 126.1(2) . . ?
O2 C5 C6 116.1(2) . . ?
C4 C5 C6 117.8(2) . . ?
N2 C6 C1 126.0(2) . . ?
N2 C6 C5 113.0(2) . . ?
C1 C6 C5 121.08(19) . . ?
N1 C7 C8 112.96(18) . . ?
N1 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C9 110.16(19) . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C10 113.9(2) . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 114.1(2) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C16 117.2(3) . . ?
C12 C11 C10 121.4(2) . . ?
C16 C11 C10 121.4(3) . . ?
C11 C12 C13 121.1(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 121.8(3) . . ?
C15 C16 H16 119.1 . . ?
C11 C16 H16 119.1 . . ?
N2 C17 C18B 112.5(3) . . ?
N2 C17 C18 109.6(3) . . ?
N2 C17 H17A 109.8 . . ?
C18B C17 H17A 90.9 . . ?
C18 C17 H17A 109.8 . . ?
N2 C17 H17B 109.8 . . ?
C18B C17 H17B 123.6 . . ?
C18 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
C19 C18 C17 112.9(5) . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 C20 112.7(5) . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 116.1(5) . . ?
C21 C20 H20A 108.3 . . ?
C19 C20 H20A 108.3 . . ?
C21 C20 H20B 108.3 . . ?
C19 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
C22 C21 C26 115.5(6) . . ?
C22 C21 C20 121.9(7) . . ?
C26 C21 C20 122.5(6) . . ?
C23 C22 C21 122.6(8) . . ?
C23 C22 H22 118.7 . . ?
C21 C22 H22 118.7 . . ?
C26 C25 C24 120.8(7) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C21 121.6(6) . . ?
C25 C26 H26 119.2 . . ?
C21 C26 H26 119.2 . . ?
C17 C18B C19B 109.9(5) . . ?
C17 C18B H18C 109.7 . . ?
C19B C18B H18C 109.7 . . ?
C17 C18B H18D 109.7 . . ?
C19B C18B H18D 109.7 . . ?
H18C C18B H18D 108.2 . . ?
C20B C19B C18B 112.6(5) . . ?
C20B C19B H19C 109.1 . . ?
C18B C19B H19C 109.1 . . ?
C20B C19B H19D 109.1 . . ?
C18B C19B H19D 109.1 . . ?
H19C C19B H19D 107.8 . . ?
C19B C20B C21B 110.6(5) . . ?
C19B C20B H20C 109.5 . . ?
C21B C20B H20C 109.5 . . ?
C19B C20B H20D 109.5 . . ?
C21B C20B H20D 109.5 . . ?
H20C C20B H20D 108.1 . . ?
C22B C21B C26B 118.6(6) . . ?
C22B C21B C20B 122.1(6) . . ?
C26B C21B C20B 119.1(6) . . ?
C21B C22B C23 120.5(7) . . ?
C21B C22B H22B 119.8 . . ?
C23 C22B H22B 119.8 . . ?
C24 C25B C26B 120.7(7) . . ?
C24 C25B H25B 119.7 . . ?
C26B C25B H25B 119.7 . . ?
C25B C26B C21B 119.5(7) . . ?
C25B C26B H26B 120.3 . . ?
C21B C26B H26B 120.3 . . ?
C22 C23 C24 123.9(5) . . ?
C24 C23 C22B 115.9(5) . . ?
C22 C23 H23 118.0 . . ?
C24 C23 H23 118.0 . . ?
C22B C23 H23 123.3 . . ?
C25B C24 C23 124.7(4) . . ?
C23 C24 C25 115.2(4) . . ?
C25B C24 H24 110.2 . . ?
C23 C24 H24 122.4 . . ?
C25 C24 H24 122.4 . . ?
C2 N1 C7 123.18(19) . . ?
C2 N1 H1N 118.0(16) . . ?
C7 N1 H1N 118.8(16) . . ?
C6 N2 C17 128.1(2) . . ?
C6 N2 H2N 115.6(17) . . ?
C17 N2 H2N 116.3(17) . . ?
H1W O3 H2W 102(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
C6 C1 C2 N1 177.1(2) . . . . ?
C6 C1 C2 C3 -3.1(3) . . . . ?
N1 C2 C3 O1 2.6(3) . . . . ?
C1 C2 C3 O1 -177.1(2) . . . . ?
N1 C2 C3 C4 -178.1(2) . . . . ?
C1 C2 C3 C4 2.2(4) . . . . ?
O1 C3 C4 C5 179.6(2) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 O2 179.0(3) . . . . ?
C3 C4 C5 C6 -1.8(4) . . . . ?
C2 C1 C6 N2 -177.4(2) . . . . ?
C2 C1 C6 C5 1.7(3) . . . . ?
O2 C5 C6 N2 -0.7(3) . . . . ?
C4 C5 C6 N2 -180.0(2) . . . . ?
O2 C5 C6 C1 -179.9(2) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
N1 C7 C8 C9 -171.1(2) . . . . ?
C7 C8 C9 C10 -174.8(2) . . . . ?
C8 C9 C10 C11 -57.2(3) . . . . ?
C9 C10 C11 C12 -62.8(3) . . . . ?
C9 C10 C11 C16 116.1(3) . . . . ?
C16 C11 C12 C13 -0.8(4) . . . . ?
C10 C11 C12 C13 178.3(3) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C12 C13 C14 C15 0.8(5) . . . . ?
C13 C14 C15 C16 -0.8(5) . . . . ?
C14 C15 C16 C11 0.0(5) . . . . ?
C12 C11 C16 C15 0.8(4) . . . . ?
C10 C11 C16 C15 -178.2(3) . . . . ?
N2 C17 C18 C19 -167.1(4) . . . . ?
C18B C17 C18 C19 -65.0(14) . . . . ?
C17 C18 C19 C20 72.3(7) . . . . ?
C18 C19 C20 C21 -179.1(6) . . . . ?
C19 C20 C21 C22 -173.5(7) . . . . ?
C19 C20 C21 C26 6.7(10) . . . . ?
C26 C21 C22 C23 -6.0(11) . . . . ?
C20 C21 C22 C23 174.2(6) . . . . ?
C24 C25 C26 C21 3.3(11) . . . . ?
C22 C21 C26 C25 1.5(11) . . . . ?
C20 C21 C26 C25 -178.7(7) . . . . ?
N2 C17 C18B C19B -157.2(4) . . . . ?
C18 C17 C18B C19B 117.3(17) . . . . ?
C17 C18B C19B C20B -177.3(5) . . . . ?
C18B C19B C20B C21B -175.8(5) . . . . ?
C19B C20B C21B C22B 85.3(8) . . . . ?
C19B C20B C21B C26B -99.9(8) . . . . ?
C26B C21B C22B C23 4.2(11) . . . . ?
C20B C21B C22B C23 179.0(6) . . . . ?
C24 C25B C26B C21B -0.9(11) . . . . ?
C22B C21B C26B C25B -3.2(11) . . . . ?
C20B C21B C26B C25B -178.1(6) . . . . ?
C21 C22 C23 C24 5.9(10) . . . . ?
C21 C22 C23 C22B -62(2) . . . . ?
C21B C22B C23 C22 120(3) . . . . ?
C21B C22B C23 C24 -1.2(9) . . . . ?
C26B C25B C24 C23 4.2(9) . . . . ?
C26B C25B C24 C25 -63.1(16) . . . . ?
C22 C23 C24 C25B -21.3(8) . . . . ?
C22B C23 C24 C25B -3.1(7) . . . . ?
C22 C23 C24 C25 -0.8(7) . . . . ?
C22B C23 C24 C25 17.4(7) . . . . ?
C26 C25 C24 C25B 119(2) . . . . ?
C26 C25 C24 C23 -3.6(9) . . . . ?
C1 C2 N1 C7 1.4(4) . . . . ?
C3 C2 N1 C7 -178.4(2) . . . . ?
C8 C7 N1 C2 176.5(2) . . . . ?
C1 C6 N2 C17 -3.0(4) . . . . ?
C5 C6 N2 C17 177.8(2) . . . . ?
C18B C17 N2 C6 -111.9(4) . . . . ?
C18 C17 N2 C6 -90.8(4) . . . . ?

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
N1 H1N O1 0.90(3) 2.15(3) 3.015(3) 159(2) 2_866
N2 H2N O3 0.87(3) 2.01(3) 2.788(3) 148(2) .
N2 H2N O2 0.87(3) 2.14(3) 2.586(3) 111(2) .
O3 H1W O1 0.89(4) 1.90(4) 2.772(3) 167(3) 1_455
O3 H2W O2 0.86(4) 1.90(4) 2.751(3) 175(3) 2_776

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.12
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_pbag111114
_database_code_depnum_ccdc_archive 'CCDC 1531553'
_audit_update_record             
;
2017-02-07 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 N2 O2'
_chemical_formula_sum            'C22 H22 N2 O2'
_chemical_formula_weight         346.42

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                   5.0542(5)
_cell_length_b                   9.8327(9)
_cell_length_c                   18.1540(17)
_cell_angle_alpha                97.826(2)
_cell_angle_beta                 91.725(2)
_cell_angle_gamma                96.982(2)
_cell_volume                     886.16(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3427
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      29.53

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9753
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  triumph
_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            13229
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0781
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         29.75
_reflns_number_total             4968
_reflns_number_gt                2940
_reflns_threshold_expression     I>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)+(0.0632P)²+1.0016P] 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         4968
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1351
_refine_ls_R_factor_gt           0.0727
_refine_ls_wR_factor_ref         0.1941
_refine_ls_wR_factor_gt          0.1620
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.6113(4) 0.8165(2) 0.59169(12) 0.0171(4) Uani 1 1 d . . .
H1 H 0.6796 0.8553 0.6403 0.020 Uiso 1 1 calc R . .
C2 C 0.7148(4) 0.7040(2) 0.55396(11) 0.0148(4) Uani 1 1 d . . .
C3 C 0.6209(4) 0.6450(2) 0.47443(12) 0.0159(4) Uani 1 1 d . . .
C4 C 0.4109(4) 0.7019(2) 0.44355(11) 0.0163(4) Uani 1 1 d . . .
H4 H 0.3423 0.6632 0.3949 0.020 Uiso 1 1 calc R . .
C5 C 0.2964(4) 0.8127(2) 0.48051(11) 0.0154(4) Uani 1 1 d . . .
C6 C 0.4077(4) 0.8722(2) 0.55808(11) 0.0147(4) Uani 1 1 d . . .
C7 C 1.0076(4) 0.6769(2) 0.65962(12) 0.0213(5) Uani 1 1 d . . .
H7A H 1.0511 0.7787 0.6707 0.026 Uiso 1 1 calc R . .
H7B H 1.1757 0.6358 0.6642 0.026 Uiso 1 1 calc R . .
C8 C 0.8179(5) 0.6273(3) 0.71681(14) 0.0316(6) Uani 1 1 d . A .
H8A H 0.6361 0.6479 0.7045 0.038 Uiso 1 1 calc R . .
H8B H 0.8110 0.5258 0.7146 0.038 Uiso 1 1 calc R . .
C9 C 0.9049(5) 0.6962(3) 0.79458(13) 0.0288(5) Uani 1 1 d . . .
C10 C 0.9364(12) 0.6230(7) 0.8505(3) 0.0400(7) Uani 0.50 1 d P A 1
H10 H 0.8999 0.5250 0.8408 0.048 Uiso 0.50 1 calc PR A 1
C11 C 1.0205(12) 0.6848(7) 0.9224(3) 0.0400(7) Uani 0.50 1 d P A 1
H11 H 1.0400 0.6295 0.9608 0.048 Uiso 0.50 1 calc PR A 1
C10B C 1.1587(13) 0.6751(7) 0.8260(3) 0.0400(7) Uani 0.50 1 d P A 2
H10B H 1.2686 0.6157 0.7993 0.048 Uiso 0.50 1 calc PR A 2
C11B C 1.2389(13) 0.7439(6) 0.8967(3) 0.0400(7) Uani 0.50 1 d P A 2
H11B H 1.4094 0.7347 0.9175 0.048 Uiso 0.50 1 calc PR A 2
C12 C 1.0746(7) 0.8254(4) 0.93710(16) 0.0495(8) Uani 1 1 d . . .
H12 H 1.1403 0.8672 0.9855 0.059 Uiso 1 1 calc R A 1
C13 C 1.0370(13) 0.9066(7) 0.8842(3) 0.0418(7) Uani 0.50 1 d P A 1
H13 H 1.0705 1.0045 0.8959 0.050 Uiso 0.50 1 calc PR A 1
C14 C 0.9492(13) 0.8462(6) 0.8131(3) 0.0418(7) Uani 0.50 1 d P A 1
H14 H 0.9178 0.9028 0.7761 0.050 Uiso 0.50 1 calc PR A 1
C13B C 0.8280(13) 0.8383(6) 0.9047(3) 0.0418(7) Uani 0.50 1 d P A 2
H13B H 0.7117 0.8937 0.9316 0.050 Uiso 0.50 1 calc PR A 2
C14B C 0.7489(14) 0.7713(6) 0.8336(3) 0.0418(7) Uani 0.50 1 d P A 2
H14B H 0.5781 0.7805 0.8130 0.050 Uiso 0.50 1 calc PR A 2
C15 C 0.3853(4) 1.0494(2) 0.66433(12) 0.0189(4) Uani 1 1 d . . .
H15A H 0.5621 1.1032 0.6608 0.023 Uiso 1 1 calc R . .
H15B H 0.4071 0.9804 0.6983 0.023 Uiso 1 1 calc R . .
C16 C 0.1948(5) 1.1461(3) 0.69698(13) 0.0290(6) Uani 1 1 d . B .
H16A H 0.1849 1.2203 0.6656 0.035 Uiso 1 1 calc R . .
H16B H 0.0141 1.0942 0.6967 0.035 Uiso 1 1 calc R . .
C17 C 0.2814(5) 1.2105(3) 0.77563(13) 0.0250(5) Uani 1 1 d . . .
C18 C 0.3538(11) 1.3452(6) 0.7896(3) 0.0366(7) Uani 0.50 1 d P B 1
H18 H 0.3444 1.4004 0.7508 0.044 Uiso 0.50 1 calc PR B 1
C19 C 0.4440(11) 1.4068(6) 0.8609(3) 0.0366(7) Uani 0.50 1 d P B 1
H19 H 0.5096 1.5026 0.8695 0.044 Uiso 0.50 1 calc PR B 1
C18B C 0.1031(12) 1.2719(6) 0.8214(3) 0.0366(7) Uani 0.50 1 d P B 2
H18B H -0.0715 1.2761 0.8017 0.044 Uiso 0.50 1 calc PR B 2
C19B C 0.1692(12) 1.3276(6) 0.8948(3) 0.0366(7) Uani 0.50 1 d P B 2
H19B H 0.0405 1.3638 0.9264 0.044 Uiso 0.50 1 calc PR B 2
C20 C 0.4393(7) 1.3282(3) 0.92115(16) 0.0436(7) Uani 1 1 d . . .
H20 H 0.4805 1.3713 0.9709 0.052 Uiso 1 1 calc R B 1
C21 C 0.3738(11) 1.1894(6) 0.9047(3) 0.0370(6) Uani 0.50 1 d P B 1
H21 H 0.3886 1.1333 0.9429 0.044 Uiso 0.50 1 calc PR B 1
C22 C 0.2856(12) 1.1264(6) 0.8334(3) 0.0370(6) Uani 0.50 1 d P B 1
H22 H 0.2295 1.0297 0.8236 0.044 Uiso 0.50 1 calc PR B 1
C21B C 0.6114(12) 1.2721(6) 0.8801(3) 0.0370(6) Uani 0.50 1 d P B 2
H21B H 0.7853 1.2683 0.9005 0.044 Uiso 0.50 1 calc PR B 2
C22B C 0.5448(12) 1.2171(6) 0.8065(3) 0.0370(6) Uani 0.50 1 d P B 2
H22B H 0.6786 1.1832 0.7760 0.044 Uiso 0.50 1 calc PR B 2
N1 N 0.8976(4) 0.64059(19) 0.58352(10) 0.0174(4) Uani 1 1 d . . .
N2 N 0.2944(4) 0.97705(18) 0.59074(10) 0.0169(4) Uani 1 1 d . . .
O1 O 0.7359(3) 0.54909(16) 0.44303(9) 0.0215(4) Uani 1 1 d . . .
O2 O 0.1117(3) 0.86834(16) 0.45453(9) 0.0218(4) Uani 1 1 d . . .
H1N H 0.953(6) 0.574(3) 0.5557(15) 0.028(7) Uiso 1 1 d . . .
H2N H 0.175(6) 1.012(3) 0.5626(17) 0.043(9) Uiso 1 1 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 C6 1.386(3) . ?
C1 C2 1.386(3) . ?
C1 H1 0.9500 . ?
C2 N1 1.316(3) . ?
C2 C3 1.520(3) . ?
C3 O1 1.249(2) . ?
C3 C4 1.395(3) . ?
C4 C5 1.396(3) . ?
C4 H4 0.9500 . ?
C5 O2 1.249(2) . ?
C5 C6 1.513(3) . ?
C6 N2 1.319(3) . ?
C7 N1 1.455(3) . ?
C7 C8 1.523(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.508(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14B 1.304(6) . ?
C9 C10 1.338(6) . ?
C9 C10B 1.438(6) . ?
C9 C14 1.455(7) . ?
C10 C11 1.394(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.364(7) . ?
C11 H11 0.9500 . ?
C10B C11B 1.390(8) . ?
C10B H10B 0.9500 . ?
C11B C12 1.381(7) . ?
C11B H11B 0.9500 . ?
C12 C13 1.353(7) . ?
C12 C13B 1.389(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(8) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C13B C14B 1.391(8) . ?
C13B H13B 0.9500 . ?
C14B H14B 0.9500 . ?
C15 N2 1.458(3) . ?
C15 C16 1.512(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.510(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.318(6) . ?
C17 C18B 1.381(6) . ?
C17 C22B 1.419(6) . ?
C17 C22 1.422(6) . ?
C18 C19 1.391(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.421(7) . ?
C19 H19 0.9500 . ?
C18B C19B 1.385(7) . ?
C18B H18B 0.9500 . ?
C19B C20 1.432(6) . ?
C19B H19B 0.9500 . ?
C20 C21B 1.288(6) . ?
C20 C21 1.355(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(7) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C21B C22B 1.388(7) . ?
C21B H21B 0.9500 . ?
C22B H22B 0.9500 . ?
N1 H1N 0.85(3) . ?
N2 H2N 0.91(3) . ?

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 119.69(19) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
N1 C2 C1 123.34(19) . . ?
N1 C2 C3 115.30(18) . . ?
C1 C2 C3 121.35(18) . . ?
O1 C3 C4 126.0(2) . . ?
O1 C3 C2 117.19(18) . . ?
C4 C3 C2 116.85(18) . . ?
C3 C4 C5 123.33(19) . . ?
C3 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
O2 C5 C4 125.5(2) . . ?
O2 C5 C6 117.08(18) . . ?
C4 C5 C6 117.45(18) . . ?
N2 C6 C1 123.48(19) . . ?
N2 C6 C5 115.36(18) . . ?
C1 C6 C5 121.15(18) . . ?
N1 C7 C8 113.0(2) . . ?
N1 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 111.6(2) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C14B C9 C10 91.1(4) . . ?
C14B C9 C10B 120.3(4) . . ?
C10 C9 C10B 55.4(4) . . ?
C14B C9 C14 54.6(4) . . ?
C10 C9 C14 116.6(4) . . ?
C10B C9 C14 94.7(4) . . ?
C14B C9 C8 120.4(4) . . ?
C10 C9 C8 121.9(4) . . ?
C10B C9 C8 119.3(3) . . ?
C14 C9 C8 121.4(3) . . ?
C9 C10 C11 122.7(6) . . ?
C9 C10 H10 118.6 . . ?
C11 C10 H10 118.6 . . ?
C12 C11 C10 119.3(5) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11B C10B C9 118.2(5) . . ?
C11B C10B H10B 120.9 . . ?
C9 C10B H10B 120.9 . . ?
C12 C11B C10B 121.1(5) . . ?
C12 C11B H11B 119.4 . . ?
C10B C11B H11B 119.4 . . ?
C13 C12 C11 121.5(4) . . ?
C13 C12 C11B 96.1(4) . . ?
C11 C12 C11B 57.1(4) . . ?
C13 C12 C13B 55.4(4) . . ?
C11 C12 C13B 90.1(4) . . ?
C11B C12 C13B 118.1(4) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C11B C12 H12 116.5 . . ?
C13B C12 H12 125.4 . . ?
C12 C13 C14 119.5(5) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C9 120.3(5) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C12 C13B C14B 121.0(5) . . ?
C12 C13B H13B 119.5 . . ?
C14B C13B H13B 119.5 . . ?
C9 C14B C13B 121.3(6) . . ?
C9 C14B H14B 119.4 . . ?
C13B C14B H14B 119.4 . . ?
N2 C15 C16 112.85(18) . . ?
N2 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
N2 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 111.79(19) . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 C18B 69.9(4) . . ?
C18 C17 C22B 78.3(4) . . ?
C18B C17 C22B 115.9(4) . . ?
C18 C17 C22 120.8(4) . . ?
C18B C17 C22 81.3(4) . . ?
C22B C17 C22 69.5(4) . . ?
C18 C17 C16 118.9(3) . . ?
C18B C17 C16 120.2(3) . . ?
C22B C17 C16 123.8(3) . . ?
C22 C17 C16 120.3(3) . . ?
C17 C18 C19 120.3(5) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C20 120.8(5) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C17 C18B C19B 122.5(5) . . ?
C17 C18B H18B 118.7 . . ?
C19B C18B H18B 118.7 . . ?
C18B C19B C20 117.3(5) . . ?
C18B C19B H19B 121.3 . . ?
C20 C19B H19B 121.3 . . ?
C21B C20 C21 68.1(4) . . ?
C21B C20 C19 78.9(4) . . ?
C21 C20 C19 117.3(4) . . ?
C21B C20 C19B 121.8(4) . . ?
C21 C20 C19B 82.0(4) . . ?
C19 C20 C19B 72.3(4) . . ?
C21B C20 H20 122.9 . . ?
C21 C20 H20 121.4 . . ?
C19 C20 H20 121.4 . . ?
C19B C20 H20 115.2 . . ?
C20 C21 C22 122.0(5) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 H21 119.0 . . ?
C21 C22 C17 118.4(5) . . ?
C21 C22 H22 120.8 . . ?
C17 C22 H22 120.8 . . ?
C20 C21B C22B 120.5(5) . . ?
C20 C21B H21B 119.7 . . ?
C22B C21B H21B 119.7 . . ?
C21B C22B C17 121.5(5) . . ?
C21B C22B H22B 119.2 . . ?
C17 C22B H22B 119.2 . . ?
C2 N1 C7 124.28(18) . . ?
C2 N1 H1N 116.8(18) . . ?
C7 N1 H1N 118.9(18) . . ?
C6 N2 C15 122.16(18) . . ?
C6 N2 H2N 117.0(19) . . ?
C15 N2 H2N 120.1(19) . . ?

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 N1 -176.1(2) . . . . ?
C6 C1 C2 C3 3.6(3) . . . . ?
N1 C2 C3 O1 -4.5(3) . . . . ?
C1 C2 C3 O1 175.8(2) . . . . ?
N1 C2 C3 C4 174.6(2) . . . . ?
C1 C2 C3 C4 -5.2(3) . . . . ?
O1 C3 C4 C5 -177.6(2) . . . . ?
C2 C3 C4 C5 3.4(3) . . . . ?
C3 C4 C5 O2 178.7(2) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C2 C1 C6 N2 178.4(2) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
O2 C5 C6 N2 0.7(3) . . . . ?
C4 C5 C6 N2 179.72(19) . . . . ?
O2 C5 C6 C1 179.5(2) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
N1 C7 C8 C9 -165.5(2) . . . . ?
C7 C8 C9 C14B 119.6(4) . . . . ?
C7 C8 C9 C10 -127.3(4) . . . . ?
C7 C8 C9 C10B -62.0(4) . . . . ?
C7 C8 C9 C14 55.0(4) . . . . ?
C14B C9 C10 C11 -53.6(7) . . . . ?
C10B C9 C10 C11 73.3(6) . . . . ?
C14 C9 C10 C11 -3.2(8) . . . . ?
C8 C9 C10 C11 179.0(5) . . . . ?
C9 C10 C11 C12 -0.3(9) . . . . ?
C14B C9 C10B C11B -4.1(8) . . . . ?
C10 C9 C10B C11B -72.0(6) . . . . ?
C14 C9 C10B C11B 47.3(6) . . . . ?
C8 C9 C10B C11B 177.6(4) . . . . ?
C9 C10B C11B C12 2.9(9) . . . . ?
C10 C11 C12 C13 3.0(8) . . . . ?
C10 C11 C12 C11B -72.6(6) . . . . ?
C10 C11 C12 C13B 51.4(6) . . . . ?
C10B C11B C12 C13 -54.7(7) . . . . ?
C10B C11B C12 C11 69.1(6) . . . . ?
C10B C11B C12 C13B -0.9(8) . . . . ?
C11 C12 C13 C14 -2.0(8) . . . . ?
C11B C12 C13 C14 53.0(7) . . . . ?
C13B C12 C13 C14 -67.2(6) . . . . ?
C12 C13 C14 C9 -1.7(9) . . . . ?
C14B C9 C14 C13 75.0(6) . . . . ?
C10 C9 C14 C13 4.2(8) . . . . ?
C10B C9 C14 C13 -49.2(6) . . . . ?
C8 C9 C14 C13 -178.0(5) . . . . ?
C13 C12 C13B C14B 77.0(6) . . . . ?
C11 C12 C13B C14B -52.2(6) . . . . ?
C11B C12 C13B C14B -0.1(8) . . . . ?
C10 C9 C14B C13B 52.9(7) . . . . ?
C10B C9 C14B C13B 3.2(8) . . . . ?
C14 C9 C14B C13B -69.5(6) . . . . ?
C8 C9 C14B C13B -178.5(5) . . . . ?
C12 C13B C14B C9 -1.1(9) . . . . ?
N2 C15 C16 C17 175.2(2) . . . . ?
C15 C16 C17 C18 114.6(4) . . . . ?
C15 C16 C17 C18B -163.1(4) . . . . ?
C15 C16 C17 C22B 19.3(5) . . . . ?
C15 C16 C17 C22 -65.1(4) . . . . ?
C18B C17 C18 C19 68.2(5) . . . . ?
C22B C17 C18 C19 -55.3(5) . . . . ?
C22 C17 C18 C19 2.1(7) . . . . ?
C16 C17 C18 C19 -177.6(4) . . . . ?
C17 C18 C19 C20 -5.2(8) . . . . ?
C18 C17 C18B C19B -70.1(6) . . . . ?
C22B C17 C18B C19B -4.8(8) . . . . ?
C22 C17 C18B C19B 57.3(6) . . . . ?
C16 C17 C18B C19B 177.4(5) . . . . ?
C17 C18B C19B C20 4.3(9) . . . . ?
C18 C19 C20 C21B 65.6(6) . . . . ?
C18 C19 C20 C21 7.5(7) . . . . ?
C18 C19 C20 C19B -63.2(5) . . . . ?
C18B C19B C20 C21B -4.1(8) . . . . ?
C18B C19B C20 C21 -62.1(6) . . . . ?
C18B C19B C20 C19 60.0(5) . . . . ?
C21B C20 C21 C22 -70.8(6) . . . . ?
C19 C20 C21 C22 -7.0(7) . . . . ?
C19B C20 C21 C22 58.2(6) . . . . ?
C20 C21 C22 C17 4.1(8) . . . . ?
C18 C17 C22 C21 -1.5(7) . . . . ?
C18B C17 C22 C21 -61.7(5) . . . . ?
C22B C17 C22 C21 60.2(5) . . . . ?
C16 C17 C22 C21 178.2(4) . . . . ?
C21 C20 C21B C22B 69.4(6) . . . . ?
C19 C20 C21B C22B -56.2(6) . . . . ?
C19B C20 C21B C22B 4.6(8) . . . . ?
C20 C21B C22B C17 -5.2(9) . . . . ?
C18 C17 C22B C21B 65.7(6) . . . . ?
C18B C17 C22B C21B 5.1(7) . . . . ?
C22 C17 C22B C21B -63.8(6) . . . . ?
C16 C17 C22B C21B -177.2(4) . . . . ?
C1 C2 N1 C7 2.1(3) . . . . ?
C3 C2 N1 C7 -177.67(19) . . . . ?
C8 C7 N1 C2 75.8(3) . . . . ?
C1 C6 N2 C15 3.7(3) . . . . ?
C5 C6 N2 C15 -177.58(19) . . . . ?
C16 C15 N2 C6 -168.6(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
N1 H1N O1 0.85(3) 2.10(3) 2.791(2) 138(2) 2_766
N2 H2N O2 0.91(3) 2.02(3) 2.863(2) 155(3) 2_576

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        29.75
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.066







####################################################################### 
# 
# 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_pblr140528
_database_code_depnum_ccdc_archive 'CCDC 1531547'
_audit_update_record             
;
2017-02-07 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 N2 O2'
_chemical_formula_sum            'C22 H22 N2 O2'
_chemical_formula_weight         346.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   4.7968(8)
_cell_length_b                   12.304(2)
_cell_length_c                   16.302(2)
_cell_angle_alpha                101.238(8)
_cell_angle_beta                 95.761(8)
_cell_angle_gamma                95.785(13)
_cell_volume                     931.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3524
_cell_measurement_theta_min      4.14
_cell_measurement_theta_max      66.49

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.632
_shelx_estimated_absorpt_T_min   0.843
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5091
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_source                   'Cu-ImuS microfocus tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8622
_diffrn_reflns_av_unetI/netI     0.0900
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.691
_diffrn_reflns_theta_max         66.806
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measured_fraction_theta_full 0.881
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_Laue_measured_fraction_full 0.881
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_point_group_measured_fraction_full 0.881
_reflns_number_total             2978
_reflns_number_gt                2248
_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    '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)+(0.2000P)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         2978
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1349
_refine_ls_R_factor_gt           0.1053
_refine_ls_wR_factor_ref         0.2991
_refine_ls_wR_factor_gt          0.2521
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_restrained_S_all      1.202
_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_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 0.6807(6) 0.2403(2) 0.10427(12) 0.0272(6) Uani 1 1 d . . . . .
H1 H 0.7685 0.2381 0.1587 0.033 Uiso 1 1 calc R U . . .
C2 C 0.4546(6) 0.1619(2) 0.06575(12) 0.0246(6) Uani 1 1 d . . . . .
C3 C 0.2958(5) 0.1692(2) -0.01897(12) 0.0256(6) Uani 1 1 d . . . . .
C4 C 0.4059(6) 0.2508(2) -0.05919(13) 0.0307(7) Uani 1 1 d . . . . .
H4 H 0.3152 0.2542 -0.1130 0.037 Uiso 1 1 calc R U . . .
C5 C 0.6408(6) 0.3276(3) -0.02498(14) 0.0323(7) Uani 1 1 d . . . . .
C6 C 0.7781(6) 0.3221(2) 0.06245(13) 0.0268(6) Uani 1 1 d . . . . .
C7 C 0.4735(6) 0.0368(3) 0.16811(14) 0.0316(7) Uani 1 1 d . . . . .
H7A H 0.6633 0.0785 0.1882 0.038 Uiso 1 1 calc R U . . .
H7B H 0.4963 -0.0433 0.1513 0.038 Uiso 1 1 calc R U . . .
C8 C 0.2931(6) 0.0519(3) 0.23982(13) 0.0296(7) Uani 1 1 d . . . . .
C9 C 0.2740(9) 0.1560(3) 0.28706(16) 0.0499(10) Uani 1 1 d . . . . .
H9 H 0.3726 0.2201 0.2740 0.060 Uiso 1 1 calc R U . . .
C10 C 0.1107(11) 0.1687(4) 0.35427(19) 0.0673(14) Uani 1 1 d . . . . .
H10 H 0.0993 0.2412 0.3861 0.081 Uiso 1 1 calc R U . . .
C11 C -0.0334(9) 0.0767(5) 0.37449(18) 0.0637(14) Uani 1 1 d . . . . .
C12 C -0.0147(9) -0.0270(5) 0.3273(2) 0.0631(13) Uani 1 1 d . . . . .
H12 H -0.1131 -0.0912 0.3403 0.076 Uiso 1 1 calc R U . . .
C13 C 0.1473(8) -0.0394(3) 0.26012(16) 0.0452(9) Uani 1 1 d . . . . .
H13 H 0.1568 -0.1119 0.2280 0.054 Uiso 1 1 calc R U . . .
C14 C -0.2183(12) 0.0883(8) 0.4451(2) 0.112(3) Uani 1 1 d . . . . .
H14A H -0.1236 0.1449 0.4933 0.169 Uiso 1 1 calc R U . . .
H14B H -0.2516 0.0165 0.4623 0.169 Uiso 1 1 calc R U . . .
H14C H -0.3993 0.1108 0.4255 0.169 Uiso 1 1 calc R U . . .
C15 C 1.1363(6) 0.4236(3) 0.17714(15) 0.0350(7) Uani 1 1 d . . . . .
H15A H 1.3219 0.4675 0.1785 0.042 Uiso 1 1 calc R U . . .
H15B H 1.1704 0.3521 0.1933 0.042 Uiso 1 1 calc R U . . .
C16 C 0.9694(6) 0.4871(3) 0.23992(15) 0.0331(7) Uani 1 1 d . . . . .
C17 C 0.8840(9) 0.5873(3) 0.22825(19) 0.0506(9) Uani 1 1 d . . . . .
H17 H 0.9339 0.6164 0.1811 0.061 Uiso 1 1 calc R U . . .
C18 C 0.7274(11) 0.6461(4) 0.2838(2) 0.0650(12) Uani 1 1 d . . . . .
H18 H 0.6668 0.7138 0.2732 0.078 Uiso 1 1 calc R U . . .
C19 C 0.6565(9) 0.6092(5) 0.3543(2) 0.0696(15) Uani 1 1 d . . . . .
C20 C 0.7374(12) 0.5088(6) 0.3651(2) 0.0775(16) Uani 1 1 d . . . . .
H20 H 0.6864 0.4803 0.4123 0.093 Uiso 1 1 calc R U . . .
C21 C 0.8925(10) 0.4468(4) 0.3089(2) 0.0602(11) Uani 1 1 d . . . . .
H21 H 0.9448 0.3773 0.3181 0.072 Uiso 1 1 calc R U . . .
C22 C 0.4851(13) 0.6757(7) 0.4138(3) 0.104(2) Uani 1 1 d . . . . .
H22A H 0.5643 0.6785 0.4721 0.156 Uiso 1 1 calc R U . . .
H22B H 0.2892 0.6402 0.4044 0.156 Uiso 1 1 calc R U . . .
H22C H 0.4906 0.7518 0.4037 0.156 Uiso 1 1 calc R U . . .
N1 N 0.3536(5) 0.0752(2) 0.09474(11) 0.0295(6) Uani 1 1 d . . . . .
H1A H 0.1971 0.0363 0.0668 0.035 Uiso 1 1 calc R U . . .
N2 N 0.9893(5) 0.4010(2) 0.09230(12) 0.0338(6) Uani 1 1 d . . . . .
H2 H 1.0462 0.4435 0.0581 0.041 Uiso 1 1 calc R U . . .
O1 O 0.0853(5) 0.1001(2) -0.04627(11) 0.0407(6) Uani 1 1 d . . . . .
O2 O 0.7491(6) 0.4013(2) -0.05854(12) 0.0532(8) 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 C2 1.384(4) . ?
C1 C6 1.390(4) . ?
C1 H1 0.9500 . ?
C2 N1 1.317(4) . ?
C2 C3 1.532(3) . ?
C3 O1 1.237(4) . ?
C3 C4 1.392(4) . ?
C4 C5 1.388(4) . ?
C4 H4 0.9500 . ?
C5 O2 1.244(4) . ?
C5 C6 1.526(3) . ?
C6 N2 1.313(4) . ?
C7 N1 1.456(3) . ?
C7 C8 1.517(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.376(5) . ?
C8 C9 1.377(5) . ?
C9 C10 1.403(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.372(8) . ?
C11 C14 1.517(5) . ?
C12 C13 1.398(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N2 1.450(3) . ?
C15 C16 1.510(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.379(5) . ?
C16 C21 1.382(5) . ?
C17 C18 1.378(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.375(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.369(9) . ?
C19 C22 1.509(6) . ?
C20 C21 1.397(7) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N1 H1A 0.8800 . ?
N2 H2 0.8800 . ?

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 C6 119.3(2) . . ?
C2 C1 H1 120.3 . . ?
C6 C1 H1 120.3 . . ?
N1 C2 C1 126.0(2) . . ?
N1 C2 C3 112.8(2) . . ?
C1 C2 C3 121.1(2) . . ?
O1 C3 C4 126.0(2) . . ?
O1 C3 C2 116.9(2) . . ?
C4 C3 C2 117.1(2) . . ?
C5 C4 C3 123.6(2) . . ?
C5 C4 H4 118.2 . . ?
C3 C4 H4 118.2 . . ?
O2 C5 C4 126.2(2) . . ?
O2 C5 C6 116.7(3) . . ?
C4 C5 C6 117.1(2) . . ?
N2 C6 C1 125.1(2) . . ?
N2 C6 C5 113.4(2) . . ?
C1 C6 C5 121.5(2) . . ?
N1 C7 C8 113.0(2) . . ?
N1 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C13 C8 C9 118.2(3) . . ?
C13 C8 C7 120.3(3) . . ?
C9 C8 C7 121.4(3) . . ?
C8 C9 C10 120.9(4) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 120.5(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 118.6(3) . . ?
C12 C11 C14 119.8(5) . . ?
C10 C11 C14 121.6(5) . . ?
C11 C12 C13 120.8(4) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 121.0(4) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C16 111.6(2) . . ?
N2 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
N2 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C21 118.1(3) . . ?
C17 C16 C15 120.0(3) . . ?
C21 C16 C15 121.9(3) . . ?
C18 C17 C16 121.1(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 121.6(5) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C20 C19 C18 117.2(4) . . ?
C20 C19 C22 122.6(5) . . ?
C18 C19 C22 120.2(6) . . ?
C19 C20 C21 122.2(4) . . ?
C19 C20 H20 118.9 . . ?
C21 C20 H20 118.9 . . ?
C16 C21 C20 119.6(5) . . ?
C16 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C2 N1 C7 126.9(2) . . ?
C2 N1 H1A 116.5 . . ?
C7 N1 H1A 116.5 . . ?
C6 N2 C15 125.2(2) . . ?
C6 N2 H2 117.4 . . ?
C15 N2 H2 117.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_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 N1 174.6(2) . . . . ?
C6 C1 C2 C3 -4.8(4) . . . . ?
N1 C2 C3 O1 5.1(3) . . . . ?
C1 C2 C3 O1 -175.4(2) . . . . ?
N1 C2 C3 C4 -173.1(2) . . . . ?
C1 C2 C3 C4 6.3(4) . . . . ?
O1 C3 C4 C5 179.0(3) . . . . ?
C2 C3 C4 C5 -2.9(4) . . . . ?
C3 C4 C5 O2 179.3(3) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C2 C1 C6 N2 179.7(3) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
O2 C5 C6 N2 2.8(4) . . . . ?
C4 C5 C6 N2 -176.6(3) . . . . ?
O2 C5 C6 C1 -177.5(3) . . . . ?
C4 C5 C6 C1 3.1(4) . . . . ?
N1 C7 C8 C13 109.0(3) . . . . ?
N1 C7 C8 C9 -72.1(3) . . . . ?
C13 C8 C9 C10 0.2(5) . . . . ?
C7 C8 C9 C10 -178.8(3) . . . . ?
C8 C9 C10 C11 0.2(5) . . . . ?
C9 C10 C11 C12 -0.4(5) . . . . ?
C9 C10 C11 C14 -178.2(3) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C14 C11 C12 C13 178.0(3) . . . . ?
C9 C8 C13 C12 -0.4(5) . . . . ?
C7 C8 C13 C12 178.5(3) . . . . ?
C11 C12 C13 C8 0.3(6) . . . . ?
N2 C15 C16 C17 -55.8(4) . . . . ?
N2 C15 C16 C21 122.8(3) . . . . ?
C21 C16 C17 C18 0.3(6) . . . . ?
C15 C16 C17 C18 178.9(3) . . . . ?
C16 C17 C18 C19 1.8(7) . . . . ?
C17 C18 C19 C20 -2.8(7) . . . . ?
C17 C18 C19 C22 179.9(4) . . . . ?
C18 C19 C20 C21 1.8(7) . . . . ?
C22 C19 C20 C21 179.0(5) . . . . ?
C17 C16 C21 C20 -1.3(6) . . . . ?
C15 C16 C21 C20 -179.9(4) . . . . ?
C19 C20 C21 C16 0.2(8) . . . . ?
C1 C2 N1 C7 -6.7(4) . . . . ?
C3 C2 N1 C7 172.7(2) . . . . ?
C8 C7 N1 C2 111.7(3) . . . . ?
C1 C6 N2 C15 -7.1(5) . . . . ?
C5 C6 N2 C15 172.5(3) . . . . ?
C16 C15 N2 C6 -78.1(4) . . . . ?

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
N1 H1A O1 0.88 2.00 2.792(3) 149.3 2
N2 H2 O2 0.88 2.06 2.800(4) 141.7 2_765
N1 H1A O1 0.88 2.00 2.792(3) 149.3 2
N2 H2 O2 0.88 2.06 2.800(4) 141.7 2_765

_refine_diff_density_max         0.593
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.127

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_pblr110322
_database_code_depnum_ccdc_archive 'CCDC 1531552'
_audit_update_record             
;
2017-02-07 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H30 N2 O6'
_chemical_formula_sum            'C26 H30 N2 O6'
_chemical_formula_weight         466.52

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           Monoclinic
_symmetry_space_group_name_H-M   ' P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc '

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

_cell_length_a                   12.5230(4)
_cell_length_b                   9.9321(3)
_cell_length_c                   20.2298(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.348(2)
_cell_angle_gamma                90.00
_cell_volume                     2343.53(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7529
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         ' sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11737
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         27.46
_reflns_number_total             5334
_reflns_number_gt                4097
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_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)+(0.0622P)²+0.8453P] 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         5334
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.1282
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.59352(13) 0.64776(17) 1.02038(8) 0.0289(3) Uani 1 1 d . . .
H1 H 0.6327 0.6214 0.9901 0.035 Uiso 1 1 calc R . .
C2 C 0.51808(13) 0.75582(17) 1.00315(8) 0.0277(3) Uani 1 1 d . . .
C3 C 0.45737(14) 0.80503(17) 1.05217(9) 0.0315(4) Uani 1 1 d . . .
C4 C 0.48047(15) 0.73554(18) 1.11574(8) 0.0329(4) Uani 1 1 d . . .
H4 H 0.4457 0.7656 1.1477 0.040 Uiso 1 1 calc R . .
C5 C 0.55235(13) 0.62412(18) 1.13421(8) 0.0307(4) Uani 1 1 d . . .
C6 C 0.60986(12) 0.57961(17) 1.08289(8) 0.0274(3) Uani 1 1 d . . .
C7 C 0.52931(15) 0.80385(19) 0.88569(8) 0.0355(4) Uani 1 1 d . . .
H7A H 0.5239 0.7070 0.8733 0.043 Uiso 1 1 calc R . .
H7B H 0.6106 0.8315 0.9002 0.043 Uiso 1 1 calc R . .
C8 C 0.45630(15) 0.88565(19) 0.82151(9) 0.0361(4) Uani 1 1 d . . .
H8A H 0.4625 0.9822 0.8345 0.043 Uiso 1 1 calc R . .
H8B H 0.4866 0.8740 0.7830 0.043 Uiso 1 1 calc R . .
C9 C 0.33101(15) 0.84484(17) 0.79437(8) 0.0323(4) Uani 1 1 d . . .
C10 C 0.29420(15) 0.72999(17) 0.75149(8) 0.0311(4) Uani 1 1 d . . .
H10 H 0.3483 0.6791 0.7390 0.037 Uiso 1 1 calc R . .
C11 C 0.18074(15) 0.68954(17) 0.72711(8) 0.0324(4) Uani 1 1 d . . .
C12 C 0.10081(15) 0.76291(19) 0.74715(9) 0.0361(4) Uani 1 1 d . . .
C13 C 0.13583(16) 0.87703(19) 0.78836(9) 0.0392(4) Uani 1 1 d . . .
H13 H 0.0820 0.9282 0.8009 0.047 Uiso 1 1 calc R . .
C14 C 0.25033(16) 0.91708(18) 0.81159(9) 0.0374(4) Uani 1 1 d . . .
H14 H 0.2735 0.9958 0.8399 0.045 Uiso 1 1 calc R . .
C15 C 0.21354(18) 0.5089(2) 0.65837(10) 0.0459(5) Uani 1 1 d . . .
H15A H 0.2413 0.5703 0.6302 0.069 Uiso 1 1 calc R . .
H15B H 0.1722 0.4340 0.6284 0.069 Uiso 1 1 calc R . .
H15C H 0.2788 0.4738 0.6983 0.069 Uiso 1 1 calc R . .
C16 C -0.09059(18) 0.7771(2) 0.74566(12) 0.0538(5) Uani 1 1 d . . .
H16A H -0.0645 0.7720 0.7975 0.081 Uiso 1 1 calc R . .
H16B H -0.1648 0.7317 0.7247 0.081 Uiso 1 1 calc R . .
H16C H -0.0986 0.8717 0.7309 0.081 Uiso 1 1 calc R . .
C17 C 0.74000(14) 0.40160(18) 1.06958(9) 0.0335(4) Uani 1 1 d . . .
H17A H 0.7022 0.4128 1.0176 0.040 Uiso 1 1 calc R . .
H17B H 0.7430 0.3042 1.0804 0.040 Uiso 1 1 calc R . .
C18 C 0.86051(14) 0.45740(19) 1.09350(9) 0.0351(4) Uani 1 1 d . . .
H18A H 0.8945 0.4537 1.1460 0.042 Uiso 1 1 calc R . .
H18B H 0.8564 0.5533 1.0794 0.042 Uiso 1 1 calc R . .
C19 C 0.93953(13) 0.38440(17) 1.06378(8) 0.0300(4) Uani 1 1 d . . .
C20 C 1.05469(14) 0.42268(18) 1.08984(9) 0.0312(4) Uani 1 1 d . . .
H20 H 1.0796 0.4919 1.1245 0.037 Uiso 1 1 calc R . .
C21 C 1.13283(13) 0.36162(17) 1.06610(8) 0.0301(4) Uani 1 1 d . . .
C22 C 1.09759(13) 0.25855(16) 1.01542(8) 0.0271(3) Uani 1 1 d . . .
C23 C 0.98399(14) 0.22088(18) 0.98884(9) 0.0331(4) Uani 1 1 d . . .
H23 H 0.9590 0.1524 0.9537 0.040 Uiso 1 1 calc R . .
C24 C 0.90520(14) 0.28340(19) 1.01348(9) 0.0360(4) Uani 1 1 d . . .
H24 H 0.8272 0.2559 0.9953 0.043 Uiso 1 1 calc R . .
C25 C 1.28751(17) 0.4842(3) 1.14746(12) 0.0601(7) Uani 1 1 d . . .
H25A H 1.2477 0.5708 1.1348 0.090 Uiso 1 1 calc R . .
H25B H 1.3701 0.4981 1.1602 0.090 Uiso 1 1 calc R . .
H25C H 1.2731 0.4453 1.1879 0.090 Uiso 1 1 calc R . .
C26 C 1.15331(16) 0.09212(19) 0.94918(10) 0.0408(4) Uani 1 1 d . . .
H26A H 1.1168 0.0217 0.9676 0.061 Uiso 1 1 calc R . .
H26B H 1.2227 0.0560 0.9440 0.061 Uiso 1 1 calc R . .
H26C H 1.1000 0.1225 0.9028 0.061 Uiso 1 1 calc R . .
N1 N 0.48940(13) 0.82551(15) 0.94431(7) 0.0336(3) Uani 1 1 d . . .
H1A H 0.4410 0.8924 0.9396 0.040 Uiso 1 1 calc R . .
N2 N 0.67341(11) 0.47080(15) 1.10518(7) 0.0326(3) Uani 1 1 d . . .
H2 H 0.6758 0.4365 1.1458 0.039 Uiso 1 1 calc R . .
O1 O 0.39196(12) 0.90322(13) 1.03092(7) 0.0450(3) Uani 1 1 d . . .
O2 O 0.57385(11) 0.55379(14) 1.18890(6) 0.0423(3) Uani 1 1 d . . .
O3 O 0.13775(11) 0.58027(13) 0.68502(6) 0.0400(3) Uani 1 1 d . . .
O4 O -0.00890(11) 0.71282(15) 0.72218(7) 0.0482(3) Uani 1 1 d . . .
O5 O 1.24637(10) 0.39469(14) 1.08843(7) 0.0452(4) Uani 1 1 d . . .
O6 O 1.18305(10) 0.20269(13) 0.99723(6) 0.0360(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 1.382(2) . ?
C1 C2 1.388(2) . ?
C1 H1 0.9500 . ?
C2 N1 1.309(2) . ?
C2 C3 1.533(2) . ?
C3 O1 1.245(2) . ?
C3 C4 1.394(2) . ?
C4 C5 1.389(2) . ?
C4 H4 0.9500 . ?
C5 O2 1.252(2) . ?
C5 C6 1.529(2) . ?
C6 N2 1.320(2) . ?
C7 N1 1.461(2) . ?
C7 C8 1.522(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.517(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.383(2) . ?
C9 C10 1.405(2) . ?
C10 C11 1.383(2) . ?
C10 H10 0.9500 . ?
C11 O3 1.363(2) . ?
C11 C12 1.412(2) . ?
C12 O4 1.373(2) . ?
C12 C13 1.381(3) . ?
C13 C14 1.394(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 O3 1.437(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O4 1.426(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N2 1.457(2) . ?
C17 C18 1.512(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.516(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C24 1.381(2) . ?
C19 C20 1.396(2) . ?
C20 C21 1.378(2) . ?
C20 H20 0.9500 . ?
C21 O5 1.3660(19) . ?
C21 C22 1.402(2) . ?
C22 O6 1.3695(18) . ?
C22 C23 1.377(2) . ?
C23 C24 1.402(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 O5 1.426(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 O6 1.423(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N1 H1A 0.8800 . ?
N2 H2 0.8800 . ?

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 117.96(14) . . ?
C6 C1 H1 121.0 . . ?
C2 C1 H1 121.0 . . ?
N1 C2 C1 125.00(15) . . ?
N1 C2 C3 112.53(14) . . ?
C1 C2 C3 122.46(14) . . ?
O1 C3 C4 126.58(15) . . ?
O1 C3 C2 116.43(15) . . ?
C4 C3 C2 116.99(14) . . ?
C5 C4 C3 122.63(15) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
O2 C5 C4 126.31(15) . . ?
O2 C5 C6 115.84(14) . . ?
C4 C5 C6 117.84(14) . . ?
N2 C6 C1 125.68(14) . . ?
N2 C6 C5 112.29(14) . . ?
C1 C6 C5 122.03(14) . . ?
N1 C7 C8 109.70(14) . . ?
N1 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
N1 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C7 112.77(14) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C14 C9 C10 118.09(16) . . ?
C14 C9 C8 121.63(16) . . ?
C10 C9 C8 120.27(16) . . ?
C11 C10 C9 121.30(16) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
O3 C11 C10 125.08(16) . . ?
O3 C11 C12 115.48(15) . . ?
C10 C11 C12 119.43(16) . . ?
O4 C12 C13 125.11(17) . . ?
O4 C12 C11 115.24(16) . . ?
C13 C12 C11 119.65(17) . . ?
C12 C13 C14 119.96(17) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 121.53(17) . . ?
C9 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C18 110.67(14) . . ?
N2 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 C19 114.65(14) . . ?
C17 C18 H18A 108.6 . . ?
C19 C18 H18A 108.6 . . ?
C17 C18 H18B 108.6 . . ?
C19 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C24 C19 C20 118.53(14) . . ?
C24 C19 C18 124.49(15) . . ?
C20 C19 C18 116.97(14) . . ?
C21 C20 C19 121.04(15) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
O5 C21 C20 124.39(15) . . ?
O5 C21 C22 115.48(13) . . ?
C20 C21 C22 120.13(14) . . ?
O6 C22 C23 125.62(14) . . ?
O6 C22 C21 115.06(13) . . ?
C23 C22 C21 119.32(14) . . ?
C22 C23 C24 120.10(15) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C19 C24 C23 120.86(15) . . ?
C19 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
O5 C25 H25A 109.5 . . ?
O5 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O5 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O6 C26 H26A 109.5 . . ?
O6 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O6 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C2 N1 C7 126.77(15) . . ?
C2 N1 H1A 116.6 . . ?
C7 N1 H1A 116.6 . . ?
C6 N2 C17 126.83(14) . . ?
C6 N2 H2 116.6 . . ?
C17 N2 H2 116.6 . . ?
C11 O3 C15 117.53(14) . . ?
C12 O4 C16 117.29(16) . . ?
C21 O5 C25 116.23(13) . . ?
C22 O6 C26 117.40(13) . . ?

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 N1 -176.33(15) . . . . ?
C6 C1 C2 C3 2.8(2) . . . . ?
N1 C2 C3 O1 -1.0(2) . . . . ?
C1 C2 C3 O1 179.77(16) . . . . ?
N1 C2 C3 C4 178.78(15) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
O1 C3 C4 C5 178.02(17) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
C3 C4 C5 O2 -177.20(17) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C2 C1 C6 N2 176.11(15) . . . . ?
C2 C1 C6 C5 -3.0(2) . . . . ?
O2 C5 C6 N2 0.6(2) . . . . ?
C4 C5 C6 N2 -178.26(15) . . . . ?
O2 C5 C6 C1 179.85(15) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
N1 C7 C8 C9 -61.68(19) . . . . ?
C7 C8 C9 C14 99.2(2) . . . . ?
C7 C8 C9 C10 -79.75(19) . . . . ?
C14 C9 C10 C11 -0.1(2) . . . . ?
C8 C9 C10 C11 178.91(14) . . . . ?
C9 C10 C11 O3 179.53(15) . . . . ?
C9 C10 C11 C12 -1.7(2) . . . . ?
O3 C11 C12 O4 0.8(2) . . . . ?
C10 C11 C12 O4 -178.08(14) . . . . ?
O3 C11 C12 C13 -178.47(15) . . . . ?
C10 C11 C12 C13 2.6(2) . . . . ?
O4 C12 C13 C14 179.00(16) . . . . ?
C11 C12 C13 C14 -1.8(3) . . . . ?
C10 C9 C14 C13 1.0(2) . . . . ?
C8 C9 C14 C13 -178.01(15) . . . . ?
C12 C13 C14 C9 0.0(3) . . . . ?
N2 C17 C18 C19 175.39(14) . . . . ?
C17 C18 C19 C24 6.2(3) . . . . ?
C17 C18 C19 C20 -173.54(15) . . . . ?
C24 C19 C20 C21 0.1(3) . . . . ?
C18 C19 C20 C21 179.78(16) . . . . ?
C19 C20 C21 O5 179.17(16) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
O5 C21 C22 O6 2.0(2) . . . . ?
C20 C21 C22 O6 -178.26(15) . . . . ?
O5 C21 C22 C23 -178.58(15) . . . . ?
C20 C21 C22 C23 1.1(3) . . . . ?
O6 C22 C23 C24 178.01(16) . . . . ?
C21 C22 C23 C24 -1.3(3) . . . . ?
C20 C19 C24 C23 -0.2(3) . . . . ?
C18 C19 C24 C23 -179.93(17) . . . . ?
C22 C23 C24 C19 0.9(3) . . . . ?
C1 C2 N1 C7 0.5(3) . . . . ?
C3 C2 N1 C7 -178.69(15) . . . . ?
C8 C7 N1 C2 167.66(16) . . . . ?
C1 C6 N2 C17 0.9(3) . . . . ?
C5 C6 N2 C17 -179.91(15) . . . . ?
C18 C17 N2 C6 90.4(2) . . . . ?
C10 C11 O3 C15 -6.2(2) . . . . ?
C12 C11 O3 C15 174.95(15) . . . . ?
C13 C12 O4 C16 -5.7(3) . . . . ?
C11 C12 O4 C16 175.09(16) . . . . ?
C20 C21 O5 C25 9.5(3) . . . . ?
C22 C21 O5 C25 -170.75(18) . . . . ?
C23 C22 O6 C26 -3.0(2) . . . . ?
C21 C22 O6 C26 176.31(15) . . . . ?

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
N1 H1A O1 0.88 2.15 2.5905(19) 110.2 .
N2 H2 O2 0.88 2.14 2.5767(18) 110.3 .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.074
