# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_liaoxb-1
_database_code_depnum_ccdc_archive 'CCDC 1040494'
_audit_update_record             
;
2014-12-20 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H25 N5 O2'
_chemical_formula_sum            'C27 H25 N5 O2'
_chemical_formula_weight         451.52
_chemical_absolute_configuration syn

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.295(5)
_cell_length_b                   12.390(4)
_cell_length_c                   16.088(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2251.5(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    49
_cell_measurement_theta_min      5.07
_cell_measurement_theta_max      12.53

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    0.087
_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      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3065
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2882
_reflns_number_gt                2321
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'XSCANS (Bruker, 1997)'
_computing_cell_refinement       'XSCANS (Bruker, 1997)'
_computing_data_reduction        'XSCANS (Bruker, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 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)+(0.0010P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0043(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2882
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0739
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
O1 O 0.00152(15) 0.46553(15) 0.88800(11) 0.0544(5) Uani 1 1 d . . .
O2 O 0.23937(17) 0.46238(16) 0.60063(10) 0.0590(5) Uani 1 1 d . . .
N1 N 0.17082(18) 0.49082(16) 0.81727(12) 0.0450(5) Uani 1 1 d . . .
N2 N 0.06593(19) 0.44633(19) 0.66860(13) 0.0531(6) Uani 1 1 d . . .
N3 N 0.18768(19) 0.63507(18) 0.91949(13) 0.0483(6) Uani 1 1 d . . .
H3 H 0.151(2) 0.620(2) 0.9638(16) 0.058 Uiso 1 1 d . . .
N4 N 0.4621(2) 0.50540(17) 0.86669(13) 0.0505(6) Uani 1 1 d . . .
N5 N 0.43884(19) 0.41377(17) 0.88923(14) 0.0522(6) Uani 1 1 d . . .
C1 C 0.0568(2) 0.4602(2) 0.82334(16) 0.0452(6) Uani 1 1 d . . .
C2 C -0.0010(2) 0.4221(2) 0.74388(17) 0.0529(7) Uani 1 1 d . . .
H2 H -0.0762 0.4612 0.7393 0.063 Uiso 1 1 calc R . .
C3 C 0.1841(2) 0.4582(2) 0.66549(16) 0.0471(7) Uani 1 1 d . . .
C4 C 0.2468(2) 0.4670(2) 0.74689(14) 0.0429(6) Uani 1 1 d . . .
H4 H 0.2887 0.3992 0.7577 0.052 Uiso 1 1 calc R . .
C5 C 0.3349(2) 0.5593(2) 0.75160(15) 0.0470(6) Uani 1 1 d . . .
H5A H 0.3018 0.6250 0.7285 0.056 Uiso 1 1 calc R . .
H5B H 0.4074 0.5417 0.7223 0.056 Uiso 1 1 calc R . .
C6 C 0.3572(2) 0.5710(2) 0.84568(15) 0.0428(6) Uani 1 1 d . . .
C7 C 0.2374(2) 0.5362(2) 0.88653(15) 0.0430(6) Uani 1 1 d . . .
H7 H 0.2500 0.4827 0.9305 0.052 Uiso 1 1 calc R . .
C8 C 0.3739(2) 0.6830(2) 0.87710(15) 0.0439(6) Uani 1 1 d . . .
C9 C 0.2763(2) 0.7133(2) 0.92328(15) 0.0468(7) Uani 1 1 d . . .
C10 C 0.2730(3) 0.8116(2) 0.96417(17) 0.0589(8) Uani 1 1 d . . .
H10 H 0.2076 0.8314 0.9958 0.071 Uiso 1 1 calc R . .
C11 C 0.3693(3) 0.8794(2) 0.95676(19) 0.0668(9) Uani 1 1 d . . .
H11 H 0.3693 0.9450 0.9848 0.080 Uiso 1 1 calc R . .
C12 C 0.4651(3) 0.8517(2) 0.90863(19) 0.0652(9) Uani 1 1 d . . .
H12 H 0.5280 0.8996 0.9029 0.078 Uiso 1 1 calc R . .
C13 C 0.4687(3) 0.7531(2) 0.86867(18) 0.0585(8) Uani 1 1 d . . .
H13 H 0.5339 0.7340 0.8365 0.070 Uiso 1 1 calc R . .
C14 C -0.0325(2) 0.3022(2) 0.75096(19) 0.0600(8) Uani 1 1 d . . .
H14A H -0.0838 0.2920 0.7987 0.072 Uiso 1 1 calc R . .
H14B H -0.0763 0.2807 0.7018 0.072 Uiso 1 1 calc R . .
C15 C 0.0728(2) 0.2309(2) 0.75988(17) 0.0512(7) Uani 1 1 d . . .
C16 C 0.1154(3) 0.2017(2) 0.83635(18) 0.0635(8) Uani 1 1 d . . .
H16 H 0.0753 0.2236 0.8840 0.076 Uiso 1 1 calc R . .
C17 C 0.2162(3) 0.1408(3) 0.8438(2) 0.0779(10) Uani 1 1 d . . .
H17 H 0.2438 0.1214 0.8962 0.093 Uiso 1 1 calc R . .
C18 C 0.2761(3) 0.1086(3) 0.7745(2) 0.0784(10) Uani 1 1 d . . .
H18 H 0.3446 0.0675 0.7794 0.094 Uiso 1 1 calc R . .
C19 C 0.2352(3) 0.1369(2) 0.6984(2) 0.0756(10) Uani 1 1 d . . .
H19 H 0.2763 0.1154 0.6512 0.091 Uiso 1 1 calc R . .
C20 C 0.1342(3) 0.1966(2) 0.69049(18) 0.0628(9) Uani 1 1 d . . .
H20 H 0.1065 0.2143 0.6378 0.075 Uiso 1 1 calc R . .
C21 C 0.0032(3) 0.4389(3) 0.58915(18) 0.0752(10) Uani 1 1 d . . .
H21A H 0.0255 0.3734 0.5613 0.113 Uiso 1 1 calc R . .
H21B H 0.0236 0.4997 0.5550 0.113 Uiso 1 1 calc R . .
H21C H -0.0806 0.4387 0.5990 0.113 Uiso 1 1 calc R . .
C22 C 0.5410(2) 0.3487(2) 0.90803(16) 0.0475(7) Uani 1 1 d . . .
C23 C 0.5187(3) 0.2436(2) 0.92742(16) 0.0513(7) Uani 1 1 d . . .
H23 H 0.4412 0.2182 0.9270 0.062 Uiso 1 1 calc R . .
C24 C 0.6095(3) 0.1750(2) 0.94758(17) 0.0576(8) Uani 1 1 d . . .
H24 H 0.5939 0.1031 0.9600 0.069 Uiso 1 1 calc R . .
C25 C 0.7238(3) 0.2133(2) 0.94922(17) 0.0553(8) Uani 1 1 d . . .
H25 H 0.7858 0.1674 0.9632 0.066 Uiso 1 1 calc R . .
C26 C 0.7461(3) 0.3180(2) 0.93043(18) 0.0583(8) Uani 1 1 d . . .
H26 H 0.8235 0.3435 0.9315 0.070 Uiso 1 1 calc R . .
C27 C 0.6555(2) 0.3864(2) 0.90993(19) 0.0617(9) Uani 1 1 d . . .
H27 H 0.6714 0.4582 0.8973 0.074 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.215(3) . ?
O2 C3 1.217(3) . ?
N1 C1 1.346(3) . ?
N1 C4 1.451(3) . ?
N1 C7 1.458(3) . ?
N2 C3 1.344(3) . ?
N2 C2 1.459(3) . ?
N2 C21 1.464(3) . ?
N3 C9 1.395(3) . ?
N3 C7 1.448(3) . ?
N3 H3 0.85(3) . ?
N4 N5 1.221(3) . ?
N4 C6 1.476(3) . ?
N5 C22 1.440(3) . ?
C1 C2 1.512(4) . ?
C2 C14 1.531(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.493(3) . ?
C4 C5 1.517(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.541(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C8 1.489(3) . ?
C6 C7 1.565(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.381(4) . ?
C8 C13 1.386(4) . ?
C9 C10 1.385(4) . ?
C10 C11 1.379(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.488(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.370(4) . ?
C15 C20 1.381(4) . ?
C16 C17 1.372(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.353(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.365(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.363(4) . ?
C22 C27 1.375(4) . ?
C23 C24 1.371(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.376(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.356(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.369(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?

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
C1 N1 C4 124.4(2) . . ?
C1 N1 C7 123.2(2) . . ?
C4 N1 C7 111.68(19) . . ?
C3 N2 C2 124.6(2) . . ?
C3 N2 C21 117.1(2) . . ?
C2 N2 C21 117.4(2) . . ?
C9 N3 C7 109.0(2) . . ?
C9 N3 H3 117.8(18) . . ?
C7 N3 H3 108.7(18) . . ?
N5 N4 C6 114.0(2) . . ?
N4 N5 C22 114.2(2) . . ?
O1 C1 N1 122.6(2) . . ?
O1 C1 C2 121.2(2) . . ?
N1 C1 C2 116.1(2) . . ?
N2 C2 C1 114.4(2) . . ?
N2 C2 C14 112.4(2) . . ?
C1 C2 C14 109.9(2) . . ?
N2 C2 H2 106.5 . . ?
C1 C2 H2 106.5 . . ?
C14 C2 H2 106.5 . . ?
O2 C3 N2 123.1(3) . . ?
O2 C3 C4 120.4(2) . . ?
N2 C3 C4 116.5(2) . . ?
N1 C4 C3 114.7(2) . . ?
N1 C4 C5 101.30(19) . . ?
C3 C4 C5 114.2(2) . . ?
N1 C4 H4 108.8 . . ?
C3 C4 H4 108.8 . . ?
C5 C4 H4 108.8 . . ?
C4 C5 C6 103.1(2) . . ?
C4 C5 H5A 111.1 . . ?
C6 C5 H5A 111.1 . . ?
C4 C5 H5B 111.1 . . ?
C6 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
N4 C6 C8 109.5(2) . . ?
N4 C6 C5 107.7(2) . . ?
C8 C6 C5 116.2(2) . . ?
N4 C6 C7 116.53(19) . . ?
C8 C6 C7 102.9(2) . . ?
C5 C6 C7 104.2(2) . . ?
N3 C7 N1 114.0(2) . . ?
N3 C7 C6 104.9(2) . . ?
N1 C7 C6 103.38(19) . . ?
N3 C7 H7 111.4 . . ?
N1 C7 H7 111.4 . . ?
C6 C7 H7 111.4 . . ?
C9 C8 C13 119.9(2) . . ?
C9 C8 C6 109.6(2) . . ?
C13 C8 C6 130.4(3) . . ?
C8 C9 C10 121.1(3) . . ?
C8 C9 N3 111.1(2) . . ?
C10 C9 N3 127.8(3) . . ?
C11 C10 C9 118.3(3) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 119.1(3) . . ?
C12 C13 H13 120.4 . . ?
C8 C13 H13 120.4 . . ?
C15 C14 C2 113.4(2) . . ?
C15 C14 H14A 108.9 . . ?
C2 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C2 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C20 117.9(3) . . ?
C16 C15 C14 121.6(3) . . ?
C20 C15 C14 120.4(3) . . ?
C15 C16 C17 121.0(3) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 120.0(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 120.7(3) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 119.5(3) . . ?
C23 C22 N5 115.8(2) . . ?
C27 C22 N5 124.7(2) . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C25 119.5(3) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C26 C25 C24 120.0(3) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.5(3) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C22 119.9(3) . . ?
C26 C27 H27 120.1 . . ?
C22 C27 H27 120.1 . . ?

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
N3 H3 O2 0.85(3) 2.73(3) 3.260(3) 122(2) 2_565

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.051
