# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_bbtuan
_database_code_depnum_ccdc_archive 'CCDC 1023785'
_audit_update_record             
;
2014-09-11 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 N3 O'
_chemical_formula_weight         329.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.4339(17)
_cell_length_b                   10.588(2)
_cell_length_c                   10.687(2)
_cell_angle_alpha                66.082(2)
_cell_angle_beta                 82.662(2)
_cell_angle_gamma                82.739(2)
_cell_volume                     862.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4938
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.33

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9566
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(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  'APEX II'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9848
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         27.33
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0
_reflns_number_total             3835
_reflns_number_gt                3337
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX-II (BRUKER-NONIUS, 2003)'
_computing_cell_refinement       
; 
  APEX-II(BRUKER-NONIUS, 2003) 
;
_computing_data_reduction        APEX-II
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    Olex2
_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)+(0.0482P)²+0.2515P] 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         3835
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
O1 O 0.53357(10) 0.11578(8) 0.84347(8) 0.0215(2) Uani 1 1 d . . .
N1 N 0.71971(11) 0.27588(9) 0.80293(9) 0.0156(2) Uani 1 1 d . . .
N2 N 0.87612(11) 0.28394(9) 0.95906(10) 0.0170(2) Uani 1 1 d . . .
H2 H 0.9090 0.2527 1.0431 0.026 Uiso 1 1 d R . .
N3 N 0.71218(11) 0.10519(9) 1.03168(9) 0.0166(2) Uani 1 1 d . . .
H3 H 0.6410 0.0644 1.0085 0.025 Uiso 1 1 d R . .
C1 C 0.76481(13) 0.22083(11) 0.93005(11) 0.0145(2) Uani 1 1 d . . .
C2 C 0.61232(13) 0.21442(11) 0.76606(11) 0.0152(2) Uani 1 1 d . . .
C3 C 0.59020(13) 0.27762(11) 0.61499(11) 0.0156(2) Uani 1 1 d . . .
C4 C 0.68105(14) 0.38354(11) 0.52233(12) 0.0182(2) Uani 1 1 d . . .
H4 H 0.7615 0.4159 0.5539 0.022 Uiso 1 1 calc R . .
C5 C 0.65395(14) 0.44166(12) 0.38421(12) 0.0213(3) Uani 1 1 d . . .
H5 H 0.7164 0.5133 0.3213 0.026 Uiso 1 1 calc R . .
C6 C 0.53605(15) 0.39552(12) 0.33775(12) 0.0218(3) Uani 1 1 d . . .
H6 H 0.5168 0.4364 0.2433 0.026 Uiso 1 1 calc R . .
C7 C 0.44637(15) 0.29002(13) 0.42876(12) 0.0232(3) Uani 1 1 d . . .
H7 H 0.3661 0.2580 0.3967 0.028 Uiso 1 1 calc R . .
C8 C 0.47351(14) 0.23070(12) 0.56706(12) 0.0200(2) Uani 1 1 d . . .
H8 H 0.4121 0.1578 0.6292 0.024 Uiso 1 1 calc R . .
C9 C 0.94127(14) 0.41111(11) 0.86228(11) 0.0171(2) Uani 1 1 d . . .
H9A H 0.9327 0.4186 0.7679 0.021 Uiso 1 1 calc R . .
H9B H 1.0567 0.4056 0.8746 0.021 Uiso 1 1 calc R . .
C10 C 0.85946(13) 0.54155(11) 0.87605(11) 0.0155(2) Uani 1 1 d . . .
C11 C 0.72222(14) 0.54015(12) 0.96350(12) 0.0190(2) Uani 1 1 d . . .
H11 H 0.6764 0.4550 1.0170 0.023 Uiso 1 1 calc R . .
C12 C 0.65116(14) 0.66215(13) 0.97354(13) 0.0231(3) Uani 1 1 d . . .
H12 H 0.5580 0.6596 1.0344 0.028 Uiso 1 1 calc R . .
C13 C 0.71572(15) 0.78718(12) 0.89516(13) 0.0236(3) Uani 1 1 d . . .
H13 H 0.6667 0.8705 0.9013 0.028 Uiso 1 1 calc R . .
C14 C 0.85291(15) 0.78955(12) 0.80743(12) 0.0217(3) Uani 1 1 d . . .
H14 H 0.8979 0.8749 0.7533 0.026 Uiso 1 1 calc R . .
C15 C 0.92460(14) 0.66773(12) 0.79843(11) 0.0187(2) Uani 1 1 d . . .
H15 H 1.0190 0.6703 0.7388 0.022 Uiso 1 1 calc R . .
C16 C 0.77247(13) 0.04380(11) 1.16415(11) 0.0155(2) Uani 1 1 d . . .
C17 C 0.88132(14) -0.07217(12) 1.19501(12) 0.0204(2) Uani 1 1 d . . .
H17 H 0.9162 -0.1098 1.1282 0.024 Uiso 1 1 calc R . .
C18 C 0.93911(15) -0.13301(12) 1.32408(13) 0.0239(3) Uani 1 1 d . . .
H18 H 1.0131 -0.2129 1.3460 0.029 Uiso 1 1 calc R . .
C19 C 0.88900(15) -0.07731(13) 1.42081(12) 0.0237(3) Uani 1 1 d . . .
H19 H 0.9292 -0.1188 1.5089 0.028 Uiso 1 1 calc R . .
C20 C 0.78042(15) 0.03865(13) 1.38986(12) 0.0231(3) Uani 1 1 d . . .
H20 H 0.7464 0.0766 1.4565 0.028 Uiso 1 1 calc R . .
C21 C 0.72145(14) 0.09930(12) 1.26130(12) 0.0195(2) Uani 1 1 d . . .
H21 H 0.6465 0.1785 1.2399 0.023 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 C2 1.2453(13) . ?
N1 C1 1.3281(14) . ?
N1 C2 1.3591(14) . ?
N2 C1 1.3509(14) . ?
N2 C9 1.4483(14) . ?
N2 H2 0.8899 . ?
N3 C1 1.3460(14) . ?
N3 C16 1.4281(14) . ?
N3 H3 0.8934 . ?
C2 C3 1.5028(15) . ?
C3 C8 1.3916(16) . ?
C3 C4 1.3959(15) . ?
C4 C5 1.3871(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3856(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.3823(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3888(16) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.5177(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3893(16) . ?
C10 C15 1.3947(15) . ?
C11 C12 1.3928(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3846(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3891(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.3882(17) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.3869(16) . ?
C16 C21 1.3875(16) . ?
C17 C18 1.3882(16) . ?
C17 H17 0.9500 . ?
C18 C19 1.3839(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.3854(18) . ?
C19 H19 0.9500 . ?
C20 C21 1.3878(16) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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 C2 120.15(9) . . ?
C1 N2 C9 123.78(9) . . ?
C1 N2 H2 121.2 . . ?
C9 N2 H2 114.9 . . ?
C1 N3 C16 123.71(9) . . ?
C1 N3 H3 114.9 . . ?
C16 N3 H3 121.2 . . ?
N1 C1 N3 125.53(10) . . ?
N1 C1 N2 117.36(10) . . ?
N3 C1 N2 117.08(10) . . ?
O1 C2 N1 126.88(10) . . ?
O1 C2 C3 119.33(10) . . ?
N1 C2 C3 113.79(9) . . ?
C8 C3 C4 119.30(10) . . ?
C8 C3 C2 118.82(10) . . ?
C4 C3 C2 121.86(10) . . ?
C5 C4 C3 120.07(11) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.21(11) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 120.03(11) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.09(11) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C3 120.29(11) . . ?
C7 C8 H8 119.9 . . ?
C3 C8 H8 119.9 . . ?
N2 C9 C10 114.44(9) . . ?
N2 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
N2 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C15 118.61(10) . . ?
C11 C10 C9 122.51(10) . . ?
C15 C10 C9 118.88(10) . . ?
C10 C11 C12 120.72(10) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 120.30(11) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.37(11) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 120.32(11) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C10 120.68(11) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C17 C16 C21 120.40(10) . . ?
C17 C16 N3 119.44(10) . . ?
C21 C16 N3 120.16(10) . . ?
C16 C17 C18 119.65(11) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 120.00(11) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.32(11) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C21 119.90(11) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 119.72(11) . . ?
C16 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?

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
C2 N1 C1 N3 -0.41(16) . . . . ?
C2 N1 C1 N2 177.70(9) . . . . ?
C16 N3 C1 N1 175.23(10) . . . . ?
C16 N3 C1 N2 -2.88(15) . . . . ?
C9 N2 C1 N1 3.55(15) . . . . ?
C9 N2 C1 N3 -178.18(10) . . . . ?
C1 N1 C2 O1 8.44(17) . . . . ?
C1 N1 C2 C3 -172.23(9) . . . . ?
O1 C2 C3 C8 4.63(16) . . . . ?
N1 C2 C3 C8 -174.75(10) . . . . ?
O1 C2 C3 C4 -176.65(10) . . . . ?
N1 C2 C3 C4 3.97(15) . . . . ?
C8 C3 C4 C5 0.44(17) . . . . ?
C2 C3 C4 C5 -178.27(10) . . . . ?
C3 C4 C5 C6 0.41(17) . . . . ?
C4 C5 C6 C7 -0.84(18) . . . . ?
C5 C6 C7 C8 0.42(18) . . . . ?
C6 C7 C8 C3 0.43(18) . . . . ?
C4 C3 C8 C7 -0.86(17) . . . . ?
C2 C3 C8 C7 177.89(10) . . . . ?
C1 N2 C9 C10 95.87(12) . . . . ?
N2 C9 C10 C11 -6.97(15) . . . . ?
N2 C9 C10 C15 172.80(9) . . . . ?
C15 C10 C11 C12 -0.03(17) . . . . ?
C9 C10 C11 C12 179.74(10) . . . . ?
C10 C11 C12 C13 0.64(18) . . . . ?
C11 C12 C13 C14 -0.62(18) . . . . ?
C12 C13 C14 C15 0.00(18) . . . . ?
C13 C14 C15 C10 0.61(17) . . . . ?
C11 C10 C15 C14 -0.59(16) . . . . ?
C9 C10 C15 C14 179.63(10) . . . . ?
C1 N3 C16 C17 -101.78(13) . . . . ?
C1 N3 C16 C21 78.70(14) . . . . ?
C21 C16 C17 C18 0.13(17) . . . . ?
N3 C16 C17 C18 -179.39(10) . . . . ?
C16 C17 C18 C19 -0.48(17) . . . . ?
C17 C18 C19 C20 0.40(18) . . . . ?
C18 C19 C20 C21 0.04(18) . . . . ?
C17 C16 C21 C20 0.31(17) . . . . ?
N3 C16 C21 C20 179.82(10) . . . . ?
C19 C20 C21 C16 -0.39(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.33
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_bbtuea
_database_code_depnum_ccdc_archive 'CCDC 1023786'
_audit_update_record             
;
2014-09-11 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;
_audit_creation_date             2013-10-08
_audit_creation_method           
; 
Olex2 1.2-beta 
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601) 
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
; 
 ? 
;
_chemical_formula_moiety         'C23 H23 N3 O2'
_chemical_formula_sum            'C23 H23 N3 O2'
_chemical_formula_weight         373.44
_chemical_melting_point          ?
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'

_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. 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.8758(16)
_cell_length_b                   18.848(3)
_cell_length_c                   9.4682(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.429(2)
_cell_angle_gamma                90
_cell_volume                     1939.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.371
_cell_measurement_theta_min      2.409
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.1488 before and 0.0444 after correction. 
The Ratio of minimum to maximum transmission is 0.9087. 
The λ/2 correction factor is 0.0015. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.519
_exptl_crystal_size_mid          0.512
_exptl_crystal_size_min          0.206
_exptl_special_details           
; 
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22873
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.439
_diffrn_reflns_theta_min         1.874
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3926
_reflns_number_total             4741
_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. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
; 
  APEX-II(BRUKER-NONIUS, 2003) 
;
_computing_data_collection       'APEX-II (BRUKER-NONIUS, 2003)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    
; 
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, 
OLEX2: a complete structure solution, refinement and analysis program. 
J. Appl. Cryst. (2009). 42, 339-341. 
;
_computing_publication_material  
; 
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, 
OLEX2: a complete structure solution, refinement and analysis program. 
J. Appl. Cryst. (2009). 42, 339-341. 
;
_computing_structure_refinement  
; 
SHELX, G.M. Sheldrick, Acta Cryst. 
(2008). A64, 112-122 
;
_computing_structure_solution    APEX-II
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4741
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.5086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1037
_refine_special_details          
; 
 ? 
;
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All N(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 C17(H17A,H17B), C15(H15A,H15B) 
2.b Aromatic/amide H refined with riding coordinates: 
 N3(H3), N2(H2), C10(H10), C4(H4), C14(H14), C11(H11), C13(H13), C8(H8), 
 C5(H5), C23(H23), C6(H6), C7(H7), C19(H19), C22(H22), C20(H20), C21(H21) 
2.c Idealised Me refined as rotating group: 
 C16(H16A,H16B,H16C) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O2 O 0.17947(8) 0.51950(4) -0.16379(8) 0.02810(19) Uani 1 1 d . . . . .
O1 O 0.50264(8) 0.43583(4) 0.60022(9) 0.0316(2) Uani 1 1 d . . . . .
N1 N 0.38149(8) 0.33722(5) 0.54342(9) 0.0209(2) Uani 1 1 d . . . . .
N3 N 0.25374(9) 0.32137(5) 0.34890(10) 0.0236(2) Uani 1 1 d . . . . .
H3 H 0.2203 0.3375 0.2689 0.028 Uiso 1 1 calc R U . . .
N2 N 0.36254(9) 0.42562(5) 0.36319(10) 0.0241(2) Uani 1 1 d . . . . .
H2 H 0.4120 0.4546 0.4112 0.029 Uiso 1 1 calc R U . . .
C2 C 0.47014(9) 0.37326(6) 0.61779(11) 0.0207(2) Uani 1 1 d . . . . .
C1 C 0.33433(9) 0.36295(6) 0.42189(11) 0.0202(2) Uani 1 1 d . . . . .
C9 C 0.31570(10) 0.44722(6) 0.22610(12) 0.0218(2) Uani 1 1 d . . . . .
C3 C 0.53438(9) 0.32967(6) 0.73188(11) 0.0196(2) Uani 1 1 d . . . . .
C12 C 0.22858(10) 0.49349(6) -0.03914(12) 0.0220(2) Uani 1 1 d . . . . .
C18 C 0.11741(10) 0.25047(6) 0.49955(11) 0.0220(2) Uani 1 1 d . . . . .
C10 C 0.38196(10) 0.43377(6) 0.10757(12) 0.0238(2) Uani 1 1 d . . . . .
H10 H 0.4575 0.4085 0.1170 0.029 Uiso 1 1 calc R U . . .
C17 C 0.21954(10) 0.25120(6) 0.39599(12) 0.0228(2) Uani 1 1 d . . . . .
H17A H 0.2931 0.2281 0.4408 0.027 Uiso 1 1 calc R U . . .
H17B H 0.1934 0.2226 0.3123 0.027 Uiso 1 1 calc R U . . .
C4 C 0.52349(10) 0.25608(6) 0.73461(12) 0.0226(2) Uani 1 1 d . . . . .
H4 H 0.4696 0.2328 0.6680 0.027 Uiso 1 1 calc R U . . .
C14 C 0.20318(10) 0.48261(6) 0.21066(12) 0.0236(2) Uani 1 1 d . . . . .
H14 H 0.1558 0.4908 0.2911 0.028 Uiso 1 1 calc R U . . .
C11 C 0.33943(10) 0.45672(6) -0.02552(12) 0.0242(2) Uani 1 1 d . . . . .
H11 H 0.3857 0.4474 -0.1063 0.029 Uiso 1 1 calc R U . . .
C13 C 0.16025(10) 0.50580(6) 0.07946(12) 0.0236(2) Uani 1 1 d . . . . .
H13 H 0.0839 0.5302 0.0700 0.028 Uiso 1 1 calc R U . . .
C8 C 0.61202(10) 0.36324(6) 0.83181(12) 0.0253(2) Uani 1 1 d . . . . .
H8 H 0.6198 0.4134 0.8307 0.030 Uiso 1 1 calc R U . . .
C5 C 0.59125(10) 0.21670(6) 0.83454(12) 0.0252(2) Uani 1 1 d . . . . .
H5 H 0.5847 0.1664 0.8349 0.030 Uiso 1 1 calc R U . . .
C23 C 0.07455(11) 0.18484(7) 0.54441(13) 0.0282(3) Uani 1 1 d . . . . .
H23 H 0.1095 0.1425 0.5093 0.034 Uiso 1 1 calc R U . . .
C6 C 0.66814(10) 0.25034(6) 0.93343(12) 0.0265(2) Uani 1 1 d . . . . .
H6 H 0.7142 0.2232 1.0017 0.032 Uiso 1 1 calc R U . . .
C7 C 0.67796(11) 0.32381(7) 0.93285(13) 0.0286(3) Uani 1 1 d . . . . .
H7 H 0.7298 0.3470 1.0016 0.034 Uiso 1 1 calc R U . . .
C19 C 0.06421(11) 0.31174(7) 0.55048(13) 0.0289(3) Uani 1 1 d . . . . .
H19 H 0.0919 0.3568 0.5203 0.035 Uiso 1 1 calc R U . . .
C15 C 0.25197(12) 0.51256(7) -0.28675(12) 0.0317(3) Uani 1 1 d . . . . .
H15A H 0.2598 0.4620 -0.3129 0.038 Uiso 1 1 calc R U . . .
H15B H 0.3355 0.5321 -0.2674 0.038 Uiso 1 1 calc R U . . .
C22 C -0.01840(12) 0.18062(8) 0.63957(14) 0.0373(3) Uani 1 1 d . . . . .
H22 H -0.0464 0.1356 0.6699 0.045 Uiso 1 1 calc R U . . .
C20 C -0.02959(12) 0.30746(8) 0.64561(14) 0.0375(3) Uani 1 1 d . . . . .
H20 H -0.0658 0.3496 0.6799 0.045 Uiso 1 1 calc R U . . .
C21 C -0.07039(12) 0.24193(9) 0.69047(14) 0.0405(3) Uani 1 1 d . . . . .
H21 H -0.1339 0.2391 0.7561 0.049 Uiso 1 1 calc R U . . .
C16 C 0.18696(14) 0.55322(8) -0.40509(14) 0.0419(3) Uani 1 1 d . . . . .
H16A H 0.2375 0.5529 -0.4883 0.063 Uiso 1 1 calc R U . . .
H16B H 0.1737 0.6023 -0.3750 0.063 Uiso 1 1 calc R U . . .
H16C H 0.1074 0.5308 -0.4288 0.063 Uiso 1 1 calc R U . . .


_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
O2 C12 1.3656(13) . ?
O2 C15 1.4395(15) . ?
O1 C2 1.2442(14) . ?
N1 C2 1.3526(13) . ?
N1 C1 1.3313(14) . ?
N3 H3 0.8800 . ?
N3 C1 1.3449(14) . ?
N3 C17 1.4492(14) . ?
N2 H2 0.8800 . ?
N2 C1 1.3464(14) . ?
N2 C9 1.4331(14) . ?
C2 C3 1.5054(14) . ?
C9 C10 1.3826(16) . ?
C9 C14 1.3959(16) . ?
C3 C4 1.3925(15) . ?
C3 C8 1.3931(15) . ?
C12 C11 1.3919(15) . ?
C12 C13 1.3920(16) . ?
C18 C17 1.5125(16) . ?
C18 C23 1.3945(16) . ?
C18 C19 1.3872(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.3927(16) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C4 H4 0.9500 . ?
C4 C5 1.3893(16) . ?
C14 H14 0.9500 . ?
C14 C13 1.3796(16) . ?
C11 H11 0.9500 . ?
C13 H13 0.9500 . ?
C8 H8 0.9500 . ?
C8 C7 1.3871(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3826(17) . ?
C23 H23 0.9500 . ?
C23 C22 1.3846(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.3889(17) . ?
C7 H7 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.3915(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5084(17) . ?
C22 H22 0.9500 . ?
C22 C21 1.382(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(2) . ?
C21 H21 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C12 O2 C15 117.31(9) . . ?
C1 N1 C2 120.46(9) . . ?
C1 N3 H3 118.5 . . ?
C1 N3 C17 122.95(9) . . ?
C17 N3 H3 118.5 . . ?
C1 N2 H2 118.5 . . ?
C1 N2 C9 123.00(9) . . ?
C9 N2 H2 118.5 . . ?
O1 C2 N1 127.35(10) . . ?
O1 C2 C3 119.17(9) . . ?
N1 C2 C3 113.47(9) . . ?
N1 C1 N3 116.78(10) . . ?
N1 C1 N2 126.17(10) . . ?
N3 C1 N2 117.01(10) . . ?
C10 C9 N2 120.37(10) . . ?
C10 C9 C14 119.17(10) . . ?
C14 C9 N2 120.46(10) . . ?
C4 C3 C2 121.32(9) . . ?
C4 C3 C8 119.30(10) . . ?
C8 C3 C2 119.27(10) . . ?
O2 C12 C11 124.35(10) . . ?
O2 C12 C13 115.77(10) . . ?
C11 C12 C13 119.88(10) . . ?
C23 C18 C17 118.01(10) . . ?
C19 C18 C17 123.12(10) . . ?
C19 C18 C23 118.87(11) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.86(10) . . ?
C11 C10 H10 119.6 . . ?
N3 C17 C18 114.39(9) . . ?
N3 C17 H17A 108.7 . . ?
N3 C17 H17B 108.7 . . ?
C18 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.11(10) . . ?
C5 C4 H4 119.9 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.50(10) . . ?
C13 C14 H14 119.8 . . ?
C12 C11 C10 119.45(10) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.11(10) . . ?
C14 C13 H13 119.9 . . ?
C3 C8 H8 119.8 . . ?
C7 C8 C3 120.38(11) . . ?
C7 C8 H8 119.8 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.29(10) . . ?
C6 C5 H5 119.9 . . ?
C18 C23 H23 119.6 . . ?
C22 C23 C18 120.79(12) . . ?
C22 C23 H23 119.6 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 119.92(10) . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 119.96(11) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.32(12) . . ?
C20 C19 H19 119.8 . . ?
O2 C15 H15A 110.2 . . ?
O2 C15 H15B 110.2 . . ?
O2 C15 C16 107.40(10) . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 H15A 110.2 . . ?
C16 C15 H15B 110.2 . . ?
C23 C22 H22 120.0 . . ?
C21 C22 C23 119.97(12) . . ?
C21 C22 H22 120.0 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.21(13) . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 119.83(12) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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 H2 O1 0.88 2.04 2.6656(12) 127.4 .

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
O2 C12 C11 C10 178.75(10) . . . . ?
O2 C12 C13 C14 -178.94(10) . . . . ?
O1 C2 C3 C4 -164.28(11) . . . . ?
O1 C2 C3 C8 11.88(15) . . . . ?
N1 C2 C3 C4 14.95(14) . . . . ?
N1 C2 C3 C8 -168.88(10) . . . . ?
N2 C9 C10 C11 -177.71(10) . . . . ?
N2 C9 C14 C13 177.52(10) . . . . ?
C2 N1 C1 N3 174.90(9) . . . . ?
C2 N1 C1 N2 -2.89(17) . . . . ?
C2 C3 C4 C5 174.99(10) . . . . ?
C2 C3 C8 C7 -176.14(10) . . . . ?
C1 N1 C2 O1 13.13(18) . . . . ?
C1 N1 C2 C3 -166.03(9) . . . . ?
C1 N3 C17 C18 84.60(13) . . . . ?
C1 N2 C9 C10 -92.74(13) . . . . ?
C1 N2 C9 C14 87.80(14) . . . . ?
C9 N2 C1 N1 174.57(10) . . . . ?
C9 N2 C1 N3 -3.22(16) . . . . ?
C9 C10 C11 C12 -0.19(17) . . . . ?
C9 C14 C13 C12 0.56(17) . . . . ?
C3 C4 C5 C6 1.18(17) . . . . ?
C3 C8 C7 C6 0.95(18) . . . . ?
C12 O2 C15 C16 -172.65(10) . . . . ?
C18 C23 C22 C21 0.45(18) . . . . ?
C18 C19 C20 C21 0.15(19) . . . . ?
C10 C9 C14 C13 -1.94(16) . . . . ?
C17 N3 C1 N1 -1.05(16) . . . . ?
C17 N3 C1 N2 176.95(10) . . . . ?
C17 C18 C23 C22 179.72(10) . . . . ?
C17 C18 C19 C20 179.95(11) . . . . ?
C4 C3 C8 C7 0.10(17) . . . . ?
C4 C5 C6 C7 -0.12(17) . . . . ?
C14 C9 C10 C11 1.75(16) . . . . ?
C11 C12 C13 C14 1.03(16) . . . . ?
C13 C12 C11 C10 -1.21(16) . . . . ?
C8 C3 C4 C5 -1.17(16) . . . . ?
C5 C6 C7 C8 -0.94(18) . . . . ?
C23 C18 C17 N3 176.70(9) . . . . ?
C23 C18 C19 C20 0.54(17) . . . . ?
C23 C22 C21 C20 0.25(19) . . . . ?
C19 C18 C17 N3 -2.71(15) . . . . ?
C19 C18 C23 C22 -0.84(17) . . . . ?
C19 C20 C21 C22 -0.55(19) . . . . ?
C15 O2 C12 C11 -4.59(16) . . . . ?
C15 O2 C12 C13 175.37(10) . . . . ?

####################################################################### 
# 
# 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_bbtunap
_database_code_depnum_ccdc_archive 'CCDC 1023787'
_audit_update_record             
;
2014-09-11 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 N3 O'
_chemical_formula_weight         379.45

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.2809(9)
_cell_length_b                   10.3681(9)
_cell_length_c                   10.6801(9)
_cell_angle_alpha                62.458(5)
_cell_angle_beta                 79.593(5)
_cell_angle_gamma                70.395(6)
_cell_volume                     950.45(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    5424
_cell_measurement_theta_min      4.57
_cell_measurement_theta_max      62.63

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9262
_exptl_absorpt_correction_T_max  0.9745
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER GADDS D8 Discover'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16951
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.57
_diffrn_reflns_theta_max         59.99
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0
_reflns_number_total             2765
_reflns_number_gt                2361
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'FRAMBO (BRUKER-NONIUS, 2003)'
_computing_cell_refinement       
; 
  CELL-NOW (Sheldrick, 2003) and SAINT (BRUKER-NONIUS, 2003) 
;
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    Olex2
_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)+(0.0612P)²+0.0299P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0128(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2765
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 0.20553(9) 0.77801(11) 0.95835(10) 0.0261(3) Uani 1 1 d . . .
N1 N 0.44253(11) 0.71365(12) 0.90644(11) 0.0181(3) Uani 1 1 d . . .
N2 N 0.31599(11) 0.64438(13) 0.79556(11) 0.0201(3) Uani 1 1 d . . .
H2 H 0.2438 0.6669 0.8481 0.024 Uiso 1 1 calc R . .
N3 N 0.55259(11) 0.60565(13) 0.75662(12) 0.0212(3) Uani 1 1 d . . .
H3 H 0.5493 0.5649 0.7014 0.025 Uiso 1 1 calc R . .
C1 C 0.43469(14) 0.65549(15) 0.82054(13) 0.0179(3) Uani 1 1 d . . .
C2 C 0.32668(13) 0.77241(14) 0.96923(13) 0.0182(3) Uani 1 1 d . . .
C3 C 0.35265(14) 0.83607(14) 1.06029(13) 0.0185(3) Uani 1 1 d . . .
C4 C 0.48517(14) 0.80178(15) 1.10298(14) 0.0206(3) Uani 1 1 d . . .
H4 H 0.5607 0.7365 1.0749 0.025 Uiso 1 1 calc R . .
C5 C 0.50757(15) 0.86232(16) 1.18624(14) 0.0250(3) Uani 1 1 d . . .
H5 H 0.5980 0.8371 1.2163 0.030 Uiso 1 1 calc R . .
C6 C 0.39786(16) 0.95965(16) 1.22546(15) 0.0271(4) Uani 1 1 d . . .
H6 H 0.4133 1.0030 1.2807 0.032 Uiso 1 1 calc R . .
C7 C 0.26566(16) 0.99370(16) 1.18395(15) 0.0274(4) Uani 1 1 d . . .
H7 H 0.1904 1.0596 1.2117 0.033 Uiso 1 1 calc R . .
C8 C 0.24257(15) 0.93182(15) 1.10184(14) 0.0232(3) Uani 1 1 d . . .
H8 H 0.1517 0.9549 1.0741 0.028 Uiso 1 1 calc R . .
C9 C 0.29215(13) 0.60096(15) 0.69517(14) 0.0185(3) Uani 1 1 d . . .
C10 C 0.20969(13) 0.49968(14) 0.74027(14) 0.0176(3) Uani 1 1 d . . .
C11 C 0.17849(13) 0.46263(15) 0.63804(14) 0.0185(3) Uani 1 1 d . . .
C12 C 0.23084(14) 0.52529(15) 0.49771(14) 0.0210(3) Uani 1 1 d . . .
H12 H 0.2103 0.5005 0.4297 0.025 Uiso 1 1 calc R . .
C13 C 0.31019(14) 0.62054(16) 0.45886(15) 0.0223(3) Uani 1 1 d . . .
H13 H 0.3458 0.6605 0.3646 0.027 Uiso 1 1 calc R . .
C14 C 0.33964(14) 0.66003(16) 0.55832(14) 0.0219(3) Uani 1 1 d . . .
H14 H 0.3932 0.7286 0.5297 0.026 Uiso 1 1 calc R . .
C15 C 0.15470(13) 0.43688(15) 0.87973(14) 0.0204(3) Uani 1 1 d . . .
H15 H 0.1749 0.4596 0.9494 0.024 Uiso 1 1 calc R . .
C16 C 0.07308(14) 0.34415(15) 0.91498(15) 0.0237(3) Uani 1 1 d . . .
H16 H 0.0367 0.3036 1.0089 0.028 Uiso 1 1 calc R . .
C17 C 0.04210(14) 0.30780(16) 0.81454(16) 0.0257(3) Uani 1 1 d . . .
H17 H -0.0149 0.2432 0.8406 0.031 Uiso 1 1 calc R . .
C18 C 0.09409(14) 0.36548(15) 0.67937(15) 0.0230(3) Uani 1 1 d . . .
H18 H 0.0732 0.3400 0.6121 0.028 Uiso 1 1 calc R . .
C19 C 0.68507(13) 0.61585(16) 0.77434(14) 0.0225(3) Uani 1 1 d . . .
H19A H 0.7541 0.5153 0.7977 0.027 Uiso 1 1 calc R . .
H19B H 0.6768 0.6397 0.8557 0.027 Uiso 1 1 calc R . .
C20 C 0.73827(13) 0.73375(15) 0.64652(14) 0.0199(3) Uani 1 1 d . . .
C21 C 0.65921(14) 0.84005(16) 0.52903(15) 0.0231(3) Uani 1 1 d . . .
H21 H 0.5671 0.8404 0.5269 0.028 Uiso 1 1 calc R . .
C22 C 0.71374(15) 0.94541(16) 0.41506(16) 0.0267(4) Uani 1 1 d . . .
H22 H 0.6586 1.0172 0.3356 0.032 Uiso 1 1 calc R . .
C23 C 0.84708(15) 0.94693(16) 0.41601(16) 0.0285(4) Uani 1 1 d . . .
H23 H 0.8840 1.0193 0.3377 0.034 Uiso 1 1 calc R . .
C24 C 0.92703(15) 0.84140(16) 0.53276(16) 0.0269(4) Uani 1 1 d . . .
H24 H 1.0191 0.8415 0.5345 0.032 Uiso 1 1 calc R . .
C25 C 0.87275(14) 0.73626(16) 0.64648(15) 0.0229(3) Uani 1 1 d . . .
H25 H 0.9282 0.6646 0.7258 0.027 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 C2 1.2513(16) . ?
N1 C1 1.3352(17) . ?
N1 C2 1.3570(17) . ?
N2 C1 1.3470(17) . ?
N2 C9 1.4239(17) . ?
N2 H2 0.8800 . ?
N3 C1 1.3451(17) . ?
N3 C19 1.4527(17) . ?
N3 H3 0.8800 . ?
C2 C3 1.5028(19) . ?
C3 C8 1.3911(19) . ?
C3 C4 1.3929(19) . ?
C4 C5 1.3873(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.3656(19) . ?
C9 C10 1.427(2) . ?
C10 C15 1.4171(19) . ?
C10 C11 1.4281(19) . ?
C11 C18 1.414(2) . ?
C11 C12 1.414(2) . ?
C12 C13 1.361(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.4104(19) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.365(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.404(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.366(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.514(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C25 1.3915(19) . ?
C20 C21 1.392(2) . ?
C21 C22 1.387(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.378(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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 C2 120.51(11) . . ?
C1 N2 C9 128.41(11) . . ?
C1 N2 H2 115.8 . . ?
C9 N2 H2 115.8 . . ?
C1 N3 C19 123.16(11) . . ?
C1 N3 H3 118.4 . . ?
C19 N3 H3 118.4 . . ?
N1 C1 N3 117.44(12) . . ?
N1 C1 N2 123.48(12) . . ?
N3 C1 N2 119.08(12) . . ?
O1 C2 N1 127.03(12) . . ?
O1 C2 C3 118.99(11) . . ?
N1 C2 C3 113.98(11) . . ?
C8 C3 C4 119.40(12) . . ?
C8 C3 C2 119.44(12) . . ?
C4 C3 C2 121.16(11) . . ?
C5 C4 C3 120.46(12) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 119.91(13) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C7 C6 C5 119.94(13) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.29(13) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C3 119.98(13) . . ?
C7 C8 H8 120.0 . . ?
C3 C8 H8 120.0 . . ?
C14 C9 N2 121.58(12) . . ?
C14 C9 C10 120.71(12) . . ?
N2 C9 C10 117.62(11) . . ?
C15 C10 C9 123.62(12) . . ?
C15 C10 C11 118.40(12) . . ?
C9 C10 C11 117.97(12) . . ?
C18 C11 C12 121.52(12) . . ?
C18 C11 C10 119.01(12) . . ?
C12 C11 C10 119.47(12) . . ?
C13 C12 C11 120.89(12) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.12(13) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 120.82(13) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C10 120.69(13) . . ?
C16 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C15 C16 C17 120.99(13) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 119.89(13) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C11 121.02(13) . . ?
C17 C18 H18 119.5 . . ?
C11 C18 H18 119.5 . . ?
N3 C19 C20 114.63(11) . . ?
N3 C19 H19A 108.6 . . ?
C20 C19 H19A 108.6 . . ?
N3 C19 H19B 108.6 . . ?
C20 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
C25 C20 C21 118.32(13) . . ?
C25 C20 C19 118.42(12) . . ?
C21 C20 C19 123.26(12) . . ?
C22 C21 C20 120.58(13) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 120.66(14) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 119.30(14) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C25 C24 C23 120.09(13) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C20 121.05(13) . . ?
C24 C25 H25 119.5 . . ?
C20 C25 H25 119.5 . . ?

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
C2 N1 C1 N3 176.95(11) . . . . ?
C2 N1 C1 N2 -3.16(19) . . . . ?
C19 N3 C1 N1 -1.53(19) . . . . ?
C19 N3 C1 N2 178.58(12) . . . . ?
C9 N2 C1 N1 172.23(12) . . . . ?
C9 N2 C1 N3 -7.9(2) . . . . ?
C1 N1 C2 O1 1.1(2) . . . . ?
C1 N1 C2 C3 -178.84(11) . . . . ?
O1 C2 C3 C8 -15.79(18) . . . . ?
N1 C2 C3 C8 164.18(12) . . . . ?
O1 C2 C3 C4 164.69(12) . . . . ?
N1 C2 C3 C4 -15.34(18) . . . . ?
C8 C3 C4 C5 0.0(2) . . . . ?
C2 C3 C4 C5 179.55(12) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C4 C5 C6 C7 1.4(2) . . . . ?
C5 C6 C7 C8 -0.6(2) . . . . ?
C6 C7 C8 C3 -0.4(2) . . . . ?
C4 C3 C8 C7 0.7(2) . . . . ?
C2 C3 C8 C7 -178.82(12) . . . . ?
C1 N2 C9 C14 -46.6(2) . . . . ?
C1 N2 C9 C10 136.95(14) . . . . ?
C14 C9 C10 C15 -178.62(12) . . . . ?
N2 C9 C10 C15 -2.13(19) . . . . ?
C14 C9 C10 C11 -0.11(19) . . . . ?
N2 C9 C10 C11 176.38(11) . . . . ?
C15 C10 C11 C18 0.15(18) . . . . ?
C9 C10 C11 C18 -178.44(12) . . . . ?
C15 C10 C11 C12 179.27(11) . . . . ?
C9 C10 C11 C12 0.68(18) . . . . ?
C18 C11 C12 C13 178.96(12) . . . . ?
C10 C11 C12 C13 -0.14(19) . . . . ?
C11 C12 C13 C14 -1.0(2) . . . . ?
N2 C9 C14 C13 -177.35(12) . . . . ?
C10 C9 C14 C13 -1.0(2) . . . . ?
C12 C13 C14 C9 1.6(2) . . . . ?
C9 C10 C15 C16 178.03(12) . . . . ?
C11 C10 C15 C16 -0.47(19) . . . . ?
C10 C15 C16 C17 0.4(2) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C16 C17 C18 C11 -0.4(2) . . . . ?
C12 C11 C18 C17 -178.82(12) . . . . ?
C10 C11 C18 C17 0.29(19) . . . . ?
C1 N3 C19 C20 -107.86(14) . . . . ?
N3 C19 C20 C25 -170.79(11) . . . . ?
N3 C19 C20 C21 9.34(18) . . . . ?
C25 C20 C21 C22 0.08(19) . . . . ?
C19 C20 C21 C22 179.95(12) . . . . ?
C20 C21 C22 C23 -0.1(2) . . . . ?
C21 C22 C23 C24 0.0(2) . . . . ?
C22 C23 C24 C25 0.0(2) . . . . ?
C23 C24 C25 C20 0.0(2) . . . . ?
C21 C20 C25 C24 -0.07(19) . . . . ?
C19 C20 C25 C24 -179.95(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        59.99
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_bbtuome
_database_code_depnum_ccdc_archive 'CCDC 1023788'
_audit_update_record             
;
2014-09-11 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 N3 O2'
_chemical_formula_weight         359.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           Trigonal
_symmetry_space_group_name_H-M   P3(2)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   9.9964(3)
_cell_length_b                   9.9964(3)
_cell_length_c                   16.0766(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1391.27(8)
_cell_formula_units_Z            3
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      5.11
_cell_measurement_theta_max      62.94

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             570
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9000
_exptl_absorpt_correction_T_max  0.9736
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER GADDS D8 Discover'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31224
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.80
_diffrn_reflns_theta_max         59.99
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0
_reflns_number_total             2729
_reflns_number_gt                2633
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'FRAMBO (BRUKER-NONIUS, 2003)'
_computing_cell_refinement       
; 
  CELL-NOW (Sheldrick, 2003) and SAINT (BRUKER-NONIUS, 2003) 
;
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    Olex2
_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)+(0.0448P)²+0.0592P] 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       0.0258(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(17)
_refine_ls_number_reflns         2729
_refine_ls_number_parameters     246
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0692
_refine_ls_wR_factor_gt          0.0686
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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
O1 O 0.44012(12) 0.91836(13) 0.00001(7) 0.0240(3) Uani 1 1 d . . .
O2 O 0.37274(13) 0.43743(12) 0.05219(7) 0.0282(3) Uani 1 1 d . . .
N1 N 0.62945(14) 0.92252(14) 0.08639(8) 0.0176(3) Uani 1 1 d . . .
N2 N 0.58861(14) 0.74777(14) 0.18934(8) 0.0193(3) Uani 1 1 d . . .
H2 H 0.5237 0.6688 0.2200 0.023 Uiso 1 1 calc R . .
N3 N 0.38265(14) 0.70034(15) 0.10631(8) 0.0191(3) Uani 1 1 d . . .
H3 H 0.3438 0.7323 0.0671 0.023 Uiso 1 1 calc R . .
C1 C 0.53279(17) 0.79106(17) 0.12580(9) 0.0166(4) Uani 1 1 d . . .
C2 C 0.57700(17) 0.97619(18) 0.02508(10) 0.0182(3) Uani 1 1 d . . .
C3 C 0.69809(18) 1.12127(18) -0.01613(10) 0.0194(4) Uani 1 1 d . . .
C4 C 0.6546(2) 1.19097(18) -0.07695(10) 0.0230(4) Uani 1 1 d . . .
H4 H 0.5483 1.1486 -0.0901 0.028 Uiso 1 1 calc R . .
C5 C 0.7642(2) 1.3214(2) -0.11868(10) 0.0266(4) Uani 1 1 d . . .
H5 H 0.7331 1.3677 -0.1603 0.032 Uiso 1 1 calc R . .
C6 C 0.9190(2) 1.3837(2) -0.09944(11) 0.0286(4) Uani 1 1 d . . .
H6 H 0.9947 1.4726 -0.1281 0.034 Uiso 1 1 calc R . .
C7 C 0.9635(2) 1.31632(19) -0.03826(11) 0.0273(4) Uani 1 1 d . . .
H7 H 1.0698 1.3594 -0.0250 0.033 Uiso 1 1 calc R . .
C8 C 0.85388(19) 1.18654(18) 0.00361(10) 0.0229(4) Uani 1 1 d . . .
H8 H 0.8852 1.1418 0.0460 0.027 Uiso 1 1 calc R . .
C9 C 0.75215(18) 0.82571(19) 0.21009(10) 0.0217(4) Uani 1 1 d . . .
H9A H 0.7633 0.8048 0.2691 0.026 Uiso 1 1 calc R . .
H9B H 0.7955 0.9385 0.2041 0.026 Uiso 1 1 calc R . .
C10 C 0.84529(18) 0.77696(18) 0.15675(9) 0.0195(4) Uani 1 1 d . . .
C11 C 1.00570(18) 0.86176(18) 0.16040(11) 0.0232(4) Uani 1 1 d . . .
H11 H 1.0547 0.9478 0.1969 0.028 Uiso 1 1 calc R . .
C12 C 1.09488(19) 0.8224(2) 0.11157(12) 0.0278(4) Uani 1 1 d . . .
H12 H 1.2043 0.8827 0.1138 0.033 Uiso 1 1 calc R . .
C13 C 1.0251(2) 0.6957(2) 0.05957(11) 0.0298(4) Uani 1 1 d . . .
H13 H 1.0863 0.6688 0.0260 0.036 Uiso 1 1 calc R . .
C14 C 0.8653(2) 0.6078(2) 0.05668(11) 0.0294(4) Uani 1 1 d . . .
H14 H 0.8168 0.5194 0.0218 0.035 Uiso 1 1 calc R . .
C15 C 0.77636(19) 0.64896(19) 0.10469(10) 0.0244(4) Uani 1 1 d . . .
H15 H 0.6669 0.5889 0.1020 0.029 Uiso 1 1 calc R . .
C16 C 0.28211(17) 0.55520(18) 0.14531(10) 0.0190(4) Uani 1 1 d . . .
C17 C 0.27738(17) 0.42053(18) 0.11684(10) 0.0209(4) Uani 1 1 d . . .
C18 C 0.1794(2) 0.2805(2) 0.15552(11) 0.0264(4) Uani 1 1 d . . .
H18 H 0.1761 0.1885 0.1372 0.032 Uiso 1 1 calc R . .
C19 C 0.0873(2) 0.2757(2) 0.22034(11) 0.0283(4) Uani 1 1 d . . .
H19 H 0.0200 0.1795 0.2462 0.034 Uiso 1 1 calc R . .
C20 C 0.09059(19) 0.40678(19) 0.24840(11) 0.0290(4) Uani 1 1 d . . .
H20 H 0.0262 0.4016 0.2932 0.035 Uiso 1 1 calc R . .
C21 C 0.18902(18) 0.54730(19) 0.21059(10) 0.0237(4) Uani 1 1 d . . .
H21 H 0.1922 0.6387 0.2299 0.028 Uiso 1 1 calc R . .
C22 C 0.3677(2) 0.3011(2) 0.02051(13) 0.0361(5) Uani 1 1 d . . .
H22A H 0.4400 0.3288 -0.0261 0.054 Uiso 1 1 calc R . .
H22B H 0.2628 0.2284 0.0013 0.054 Uiso 1 1 calc R . .
H22C H 0.3968 0.2529 0.0646 0.054 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 C2 1.2562(19) . ?
O2 C17 1.362(2) . ?
O2 C22 1.431(2) . ?
N1 C1 1.3387(19) . ?
N1 C2 1.347(2) . ?
N2 C1 1.336(2) . ?
N2 C9 1.455(2) . ?
N2 H2 0.8800 . ?
N3 C1 1.346(2) . ?
N3 C16 1.432(2) . ?
N3 H3 0.8800 . ?
C2 C3 1.501(2) . ?
C3 C4 1.391(2) . ?
C3 C8 1.391(2) . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.514(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.389(2) . ?
C10 C11 1.391(2) . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.378(2) . ?
C16 C17 1.400(2) . ?
C17 C18 1.391(2) . ?
C18 C19 1.375(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.371(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
C17 O2 C22 117.63(13) . . ?
C1 N1 C2 120.23(13) . . ?
C1 N2 C9 122.78(12) . . ?
C1 N2 H2 118.6 . . ?
C9 N2 H2 118.6 . . ?
C1 N3 C16 124.19(13) . . ?
C1 N3 H3 117.9 . . ?
C16 N3 H3 117.9 . . ?
N2 C1 N1 117.82(13) . . ?
N2 C1 N3 117.74(13) . . ?
N1 C1 N3 124.43(14) . . ?
O1 C2 N1 127.06(14) . . ?
O1 C2 C3 118.02(14) . . ?
N1 C2 C3 114.92(13) . . ?
C4 C3 C8 118.86(15) . . ?
C4 C3 C2 119.43(14) . . ?
C8 C3 C2 121.69(14) . . ?
C5 C4 C3 120.88(16) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 119.70(16) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 119.89(15) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.35(16) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C3 120.30(15) . . ?
C7 C8 H8 119.9 . . ?
C3 C8 H8 119.9 . . ?
N2 C9 C10 113.88(13) . . ?
N2 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
N2 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C15 C10 C11 118.46(15) . . ?
C15 C10 C9 122.40(14) . . ?
C11 C10 C9 119.14(14) . . ?
C12 C11 C10 120.86(15) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.18(15) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.65(16) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 120.01(16) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 120.82(15) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C21 C16 C17 119.77(14) . . ?
C21 C16 N3 120.21(14) . . ?
C17 C16 N3 120.02(15) . . ?
O2 C17 C18 124.26(15) . . ?
O2 C17 C16 116.42(14) . . ?
C18 C17 C16 119.32(15) . . ?
C19 C18 C17 119.76(16) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 121.34(16) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 119.29(16) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C16 C21 C20 120.52(16) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
C9 N2 C1 N1 -8.2(2) . . . . ?
C9 N2 C1 N3 172.53(13) . . . . ?
C2 N1 C1 N2 -176.10(13) . . . . ?
C2 N1 C1 N3 3.1(2) . . . . ?
C16 N3 C1 N2 -4.7(2) . . . . ?
C16 N3 C1 N1 176.04(14) . . . . ?
C1 N1 C2 O1 2.5(2) . . . . ?
C1 N1 C2 C3 -177.82(13) . . . . ?
O1 C2 C3 C4 3.4(2) . . . . ?
N1 C2 C3 C4 -176.38(14) . . . . ?
O1 C2 C3 C8 -175.22(14) . . . . ?
N1 C2 C3 C8 5.0(2) . . . . ?
C8 C3 C4 C5 1.3(2) . . . . ?
C2 C3 C4 C5 -177.28(14) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 C3 0.9(2) . . . . ?
C4 C3 C8 C7 -1.6(2) . . . . ?
C2 C3 C8 C7 176.97(14) . . . . ?
C1 N2 C9 C10 -80.69(18) . . . . ?
N2 C9 C10 C15 -12.0(2) . . . . ?
N2 C9 C10 C11 168.74(14) . . . . ?
C15 C10 C11 C12 1.8(2) . . . . ?
C9 C10 C11 C12 -178.92(15) . . . . ?
C10 C11 C12 C13 -1.4(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 1.2(3) . . . . ?
C13 C14 C15 C10 -0.7(3) . . . . ?
C11 C10 C15 C14 -0.8(2) . . . . ?
C9 C10 C15 C14 179.96(15) . . . . ?
C1 N3 C16 C21 95.78(18) . . . . ?
C1 N3 C16 C17 -84.62(19) . . . . ?
C22 O2 C17 C18 2.1(2) . . . . ?
C22 O2 C17 C16 -178.55(14) . . . . ?
C21 C16 C17 O2 -179.93(13) . . . . ?
N3 C16 C17 O2 0.5(2) . . . . ?
C21 C16 C17 C18 -0.6(2) . . . . ?
N3 C16 C17 C18 179.84(14) . . . . ?
O2 C17 C18 C19 -179.88(15) . . . . ?
C16 C17 C18 C19 0.8(2) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C17 C16 C21 C20 0.0(2) . . . . ?
N3 C16 C21 C20 179.63(15) . . . . ?
C19 C20 C21 C16 0.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        59.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.032
####################################################################### 
# 
# 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_rkb
_database_code_depnum_ccdc_archive 'CCDC 1023789'
_audit_update_record             
;
2014-09-11 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 N3 O'
_chemical_formula_weight         343.42

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

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

_cell_length_a                   12.6374(15)
_cell_length_b                   12.7890(15)
_cell_length_c                   12.8040(15)
_cell_angle_alpha                73.447(2)
_cell_angle_beta                 75.957(2)
_cell_angle_gamma                74.303(2)
_cell_volume                     1878.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.57

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.61
_exptl_crystal_size_min          0.53
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9522
_exptl_absorpt_correction_T_max  0.9608
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'APEX II'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25111
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         27.50
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0
_reflns_number_total             8452
_reflns_number_gt                7050
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX-II (BRUKER-NONIUS, 2003)'
_computing_cell_refinement       
; 
  APEX-II(BRUKER-NONIUS, 2003) 
;
_computing_data_reduction        APEX-II
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    Olex2
_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)+(0.0597P)²+0.3909P] 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         8452
_refine_ls_number_parameters     471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.1098
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 -0.13443(7) 1.20519(7) 0.74936(8) 0.0337(2) Uani 1 1 d . . .
N1 N -0.20962(8) 1.04846(8) 0.78998(8) 0.0256(2) Uani 1 1 d . . .
N2 N -0.02200(8) 1.01974(8) 0.69696(8) 0.0261(2) Uani 1 1 d . . .
H2 H -0.0254 1.0904 0.6930 0.031 Uiso 1 1 calc R . .
N3 N -0.11236(9) 0.87258(8) 0.77618(8) 0.0294(2) Uani 1 1 d . . .
H3 H -0.0544 0.8286 0.7451 0.035 Uiso 1 1 calc R . .
C1 C -0.21488(9) 1.15746(9) 0.77828(9) 0.0243(2) Uani 1 1 d . . .
C2 C -0.33093(9) 1.22582(10) 0.80131(9) 0.0251(2) Uani 1 1 d . . .
C3 C -0.42163(10) 1.17622(11) 0.85255(10) 0.0325(3) Uani 1 1 d . . .
H3A H -0.4106 1.0971 0.8752 0.039 Uiso 1 1 calc R . .
C4 C -0.52830(11) 1.24243(13) 0.87053(11) 0.0408(3) Uani 1 1 d . . .
H4 H -0.5900 1.2085 0.9060 0.049 Uiso 1 1 calc R . .
C5 C -0.54501(11) 1.35731(13) 0.83717(11) 0.0418(3) Uani 1 1 d . . .
H5 H -0.6180 1.4023 0.8500 0.050 Uiso 1 1 calc R . .
C6 C -0.45533(11) 1.40665(12) 0.78510(11) 0.0384(3) Uani 1 1 d . . .
H6 H -0.4670 1.4857 0.7613 0.046 Uiso 1 1 calc R . .
C7 C -0.34844(10) 1.34147(10) 0.76731(10) 0.0303(3) Uani 1 1 d . . .
H7 H -0.2871 1.3760 0.7318 0.036 Uiso 1 1 calc R . .
C8 C -0.11396(9) 0.98150(9) 0.75436(9) 0.0240(2) Uani 1 1 d . . .
C9 C 0.07934(9) 0.96301(9) 0.64202(9) 0.0236(2) Uani 1 1 d . . .
C10 C 0.17852(10) 0.98263(10) 0.65245(9) 0.0263(2) Uani 1 1 d . . .
H10 H 0.1775 1.0278 0.7003 0.032 Uiso 1 1 calc R . .
C11 C 0.27919(10) 0.93652(10) 0.59327(10) 0.0288(3) Uani 1 1 d . . .
H11 H 0.3465 0.9507 0.6011 0.035 Uiso 1 1 calc R . .
C12 C 0.28367(10) 0.86999(10) 0.52277(9) 0.0293(3) Uani 1 1 d . . .
C13 C 0.18351(10) 0.85055(10) 0.51380(9) 0.0287(3) Uani 1 1 d . . .
H13 H 0.1847 0.8048 0.4665 0.034 Uiso 1 1 calc R . .
C14 C 0.08186(10) 0.89625(9) 0.57226(9) 0.0261(2) Uani 1 1 d . . .
H14 H 0.0145 0.8820 0.5646 0.031 Uiso 1 1 calc R . .
C15 C 0.39288(12) 0.82254(13) 0.45553(12) 0.0421(3) Uani 1 1 d . . .
H15A H 0.4004 0.7421 0.4661 0.063 Uiso 1 1 calc R . .
H15B H 0.4550 0.8355 0.4799 0.063 Uiso 1 1 calc R . .
H15C H 0.3941 0.8593 0.3770 0.063 Uiso 1 1 calc R . .
C16 C -0.20309(11) 0.82426(10) 0.84950(10) 0.0307(3) Uani 1 1 d . . .
H16A H -0.2410 0.8715 0.9028 0.037 Uiso 1 1 calc R . .
H16B H -0.1706 0.7497 0.8925 0.037 Uiso 1 1 calc R . .
C17 C -0.29002(10) 0.81139(9) 0.79421(9) 0.0262(2) Uani 1 1 d . . .
C18 C -0.35905(11) 0.73850(11) 0.85490(10) 0.0334(3) Uani 1 1 d . . .
H18 H -0.3479 0.6969 0.9272 0.040 Uiso 1 1 calc R . .
C19 C -0.44365(11) 0.72552(12) 0.81168(12) 0.0396(3) Uani 1 1 d . . .
H19 H -0.4902 0.6755 0.8543 0.048 Uiso 1 1 calc R . .
C20 C -0.46049(11) 0.78530(12) 0.70662(12) 0.0388(3) Uani 1 1 d . . .
H20 H -0.5188 0.7770 0.6768 0.047 Uiso 1 1 calc R . .
C21 C -0.39200(12) 0.85718(11) 0.64519(12) 0.0389(3) Uani 1 1 d . . .
H21 H -0.4030 0.8979 0.5726 0.047 Uiso 1 1 calc R . .
C22 C -0.30702(11) 0.87064(10) 0.68848(11) 0.0330(3) Uani 1 1 d . . .
H22 H -0.2605 0.9206 0.6455 0.040 Uiso 1 1 calc R . .
O1B O 0.01831(7) 0.66367(7) 0.74556(8) 0.0336(2) Uani 1 1 d . . .
N1B N 0.05787(8) 0.47319(8) 0.82888(8) 0.0252(2) Uani 1 1 d . . .
N2B N -0.06459(8) 0.52366(8) 0.70059(8) 0.0268(2) Uani 1 1 d . . .
H2B H -0.0612 0.5933 0.6933 0.032 Uiso 1 1 calc R . .
N3B N -0.01891(8) 0.34153(8) 0.80182(8) 0.0272(2) Uani 1 1 d . . .
H3B H -0.0555 0.3223 0.7625 0.033 Uiso 1 1 calc R . .
C1B C 0.06740(9) 0.57949(9) 0.80875(9) 0.0241(2) Uani 1 1 d . . .
C2B C 0.14567(9) 0.59849(9) 0.86918(9) 0.0239(2) Uani 1 1 d . . .
C3B C 0.17397(10) 0.52581(10) 0.96706(10) 0.0284(2) Uani 1 1 d . . .
H3BA H 0.1463 0.4592 0.9959 0.034 Uiso 1 1 calc R . .
C4B C 0.24248(11) 0.55029(11) 1.02276(10) 0.0340(3) Uani 1 1 d . . .
H4B H 0.2603 0.5012 1.0904 0.041 Uiso 1 1 calc R . .
C5B C 0.28482(11) 0.64599(12) 0.97995(11) 0.0354(3) Uani 1 1 d . . .
H5B H 0.3318 0.6625 1.0180 0.042 Uiso 1 1 calc R . .
C6B C 0.25865(11) 0.71755(12) 0.88163(11) 0.0354(3) Uani 1 1 d . . .
H6B H 0.2888 0.7826 0.8515 0.042 Uiso 1 1 calc R . .
C7B C 0.18855(10) 0.69448(10) 0.82708(10) 0.0295(3) Uani 1 1 d . . .
H7B H 0.1696 0.7447 0.7604 0.035 Uiso 1 1 calc R . .
C8B C -0.00847(9) 0.44756(9) 0.77632(9) 0.0245(2) Uani 1 1 d . . .
C9B C -0.12831(9) 0.50892(9) 0.63081(9) 0.0256(2) Uani 1 1 d . . .
C10B C -0.22738(10) 0.58623(10) 0.61570(10) 0.0314(3) Uani 1 1 d . . .
H10B H -0.2531 0.6431 0.6558 0.038 Uiso 1 1 calc R . .
C11B C -0.28887(11) 0.58072(12) 0.54239(11) 0.0376(3) Uani 1 1 d . . .
H11B H -0.3566 0.6343 0.5327 0.045 Uiso 1 1 calc R . .
C12B C -0.25366(12) 0.49837(12) 0.48256(10) 0.0363(3) Uani 1 1 d . . .
C13B C -0.15379(11) 0.42277(11) 0.49791(10) 0.0344(3) Uani 1 1 d . . .
H13B H -0.1277 0.3663 0.4573 0.041 Uiso 1 1 calc R . .
C14B C -0.09090(10) 0.42705(10) 0.57078(10) 0.0296(3) Uani 1 1 d . . .
H14B H -0.0226 0.3743 0.5796 0.035 Uiso 1 1 calc R . .
C15B C -0.32095(15) 0.49296(16) 0.40264(13) 0.0546(4) Uani 1 1 d . . .
H15D H -0.3023 0.5443 0.3312 0.082 Uiso 1 1 calc R . .
H15E H -0.4008 0.5145 0.4322 0.082 Uiso 1 1 calc R . .
H15F H -0.3036 0.4166 0.3926 0.082 Uiso 1 1 calc R . .
C16B C 0.02741(10) 0.25652(10) 0.89148(10) 0.0305(3) Uani 1 1 d . . .
H16C H -0.0262 0.2076 0.9289 0.037 Uiso 1 1 calc R . .
H16D H 0.0354 0.2937 0.9464 0.037 Uiso 1 1 calc R . .
C17B C 0.13960(11) 0.18448(10) 0.85531(11) 0.0321(3) Uani 1 1 d . . .
C18B C 0.21223(11) 0.22143(12) 0.75941(13) 0.0411(3) Uani 1 1 d . . .
H18B H 0.1901 0.2927 0.7124 0.049 Uiso 1 1 calc R . .
C19B C 0.31691(12) 0.15509(15) 0.73160(17) 0.0568(5) Uani 1 1 d . . .
H19B H 0.3655 0.1812 0.6655 0.068 Uiso 1 1 calc R . .
C20B C 0.35054(15) 0.05250(16) 0.7987(2) 0.0643(6) Uani 1 1 d . . .
H20B H 0.4225 0.0079 0.7798 0.077 Uiso 1 1 calc R . .
C21B C 0.27978(18) 0.01452(14) 0.89352(18) 0.0634(6) Uani 1 1 d . . .
H21B H 0.3030 -0.0567 0.9401 0.076 Uiso 1 1 calc R . .
C22B C 0.17356(15) 0.07973(12) 0.92229(13) 0.0475(4) Uani 1 1 d . . .
H22B H 0.1248 0.0523 0.9876 0.057 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 1.2521(14) . ?
N1 C8 1.3407(14) . ?
N1 C1 1.3438(15) . ?
N2 C8 1.3484(15) . ?
N2 C9 1.4186(14) . ?
N2 H2 0.8800 . ?
N3 C8 1.3358(15) . ?
N3 C16 1.4520(16) . ?
N3 H3 0.8800 . ?
C1 C2 1.4984(15) . ?
C2 C7 1.3887(17) . ?
C2 C3 1.3921(17) . ?
C3 C4 1.3894(18) . ?
C3 H3A 0.9500 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.3861(17) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C10 1.3865(16) . ?
C9 C14 1.3905(16) . ?
C10 C11 1.3861(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3889(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3907(18) . ?
C12 C15 1.5107(17) . ?
C13 C14 1.3887(17) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.5088(17) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C22 1.3862(17) . ?
C17 C18 1.3900(17) . ?
C18 C19 1.383(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.380(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.379(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.3906(19) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
O1B C1B 1.2587(14) . ?
N1B C1B 1.3428(15) . ?
N1B C8B 1.3459(15) . ?
N2B C8B 1.3465(15) . ?
N2B C9B 1.4175(15) . ?
N2B H2B 0.8800 . ?
N3B C8B 1.3365(15) . ?
N3B C16B 1.4537(15) . ?
N3B H3B 0.8800 . ?
C1B C2B 1.4981(16) . ?
C2B C7B 1.3902(17) . ?
C2B C3B 1.3916(16) . ?
C3B C4B 1.3891(18) . ?
C3B H3BA 0.9500 . ?
C4B C5B 1.3837(19) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3833(18) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.3852(17) . ?
C6B H6B 0.9500 . ?
C7B H7B 0.9500 . ?
C9B C10B 1.3861(16) . ?
C9B C14B 1.3875(16) . ?
C10B C11B 1.3826(18) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.391(2) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.385(2) . ?
C12B C15B 1.5065(19) . ?
C13B C14B 1.3847(18) . ?
C13B H13B 0.9500 . ?
C14B H14B 0.9500 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C16B C17B 1.5136(17) . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
C17B C22B 1.3882(19) . ?
C17B C18B 1.389(2) . ?
C18B C19B 1.3903(19) . ?
C18B H18B 0.9500 . ?
C19B C20B 1.369(3) . ?
C19B H19B 0.9500 . ?
C20B C21B 1.372(3) . ?
C20B H20B 0.9500 . ?
C21B C22B 1.401(2) . ?
C21B H21B 0.9500 . ?
C22B H22B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 120.55(10) . . ?
C8 N2 C9 129.58(10) . . ?
C8 N2 H2 115.2 . . ?
C9 N2 H2 115.2 . . ?
C8 N3 C16 122.20(10) . . ?
C8 N3 H3 118.9 . . ?
C16 N3 H3 118.9 . . ?
O1 C1 N1 126.77(10) . . ?
O1 C1 C2 118.83(10) . . ?
N1 C1 C2 114.40(10) . . ?
C7 C2 C3 119.43(11) . . ?
C7 C2 C1 118.88(11) . . ?
C3 C2 C1 121.66(11) . . ?
C4 C3 C2 119.96(13) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C5 C4 C3 120.31(13) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.83(12) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 120.37(13) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C2 120.10(12) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
N3 C8 N1 117.33(10) . . ?
N3 C8 N2 119.71(10) . . ?
N1 C8 N2 122.95(10) . . ?
C10 C9 C14 119.45(10) . . ?
C10 C9 N2 117.88(10) . . ?
C14 C9 N2 122.48(10) . . ?
C11 C10 C9 120.18(11) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 121.37(11) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C13 117.72(11) . . ?
C11 C12 C15 121.47(12) . . ?
C13 C12 C15 120.79(12) . . ?
C14 C13 C12 121.70(11) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C9 119.58(11) . . ?
C13 C14 H14 120.2 . . ?
C9 C14 H14 120.2 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C17 115.95(10) . . ?
N3 C16 H16A 108.3 . . ?
C17 C16 H16A 108.3 . . ?
N3 C16 H16B 108.3 . . ?
C17 C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
C22 C17 C18 118.59(12) . . ?
C22 C17 C16 123.76(11) . . ?
C18 C17 C16 117.61(11) . . ?
C19 C18 C17 121.08(12) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 119.99(12) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 119.52(13) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.64(13) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 120.18(12) . . ?
C17 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C1B N1B C8B 119.73(10) . . ?
C8B N2B C9B 129.95(10) . . ?
C8B N2B H2B 115.0 . . ?
C9B N2B H2B 115.0 . . ?
C8B N3B C16B 123.10(10) . . ?
C8B N3B H3B 118.5 . . ?
C16B N3B H3B 118.5 . . ?
O1B C1B N1B 127.41(11) . . ?
O1B C1B C2B 117.14(10) . . ?
N1B C1B C2B 115.45(10) . . ?
C7B C2B C3B 119.11(11) . . ?
C7B C2B C1B 118.29(10) . . ?
C3B C2B C1B 122.57(11) . . ?
C4B C3B C2B 120.22(11) . . ?
C4B C3B H3BA 119.9 . . ?
C2B C3B H3BA 119.9 . . ?
C5B C4B C3B 120.13(11) . . ?
C5B C4B H4B 119.9 . . ?
C3B C4B H4B 119.9 . . ?
C6B C5B C4B 119.92(12) . . ?
C6B C5B H5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C5B C6B C7B 120.06(12) . . ?
C5B C6B H6B 120.0 . . ?
C7B C6B H6B 120.0 . . ?
C6B C7B C2B 120.53(11) . . ?
C6B C7B H7B 119.7 . . ?
C2B C7B H7B 119.7 . . ?
N3B C8B N1B 117.81(10) . . ?
N3B C8B N2B 119.18(11) . . ?
N1B C8B N2B 123.01(10) . . ?
C10B C9B C14B 119.43(11) . . ?
C10B C9B N2B 117.62(10) . . ?
C14B C9B N2B 122.72(11) . . ?
C11B C10B C9B 120.13(11) . . ?
C11B C10B H10B 119.9 . . ?
C9B C10B H10B 119.9 . . ?
C10B C11B C12B 121.36(12) . . ?
C10B C11B H11B 119.3 . . ?
C12B C11B H11B 119.3 . . ?
C13B C12B C11B 117.57(12) . . ?
C13B C12B C15B 121.32(13) . . ?
C11B C12B C15B 121.09(14) . . ?
C14B C13B C12B 121.93(12) . . ?
C14B C13B H13B 119.0 . . ?
C12B C13B H13B 119.0 . . ?
C13B C14B C9B 119.58(12) . . ?
C13B C14B H14B 120.2 . . ?
C9B C14B H14B 120.2 . . ?
C12B C15B H15D 109.5 . . ?
C12B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C12B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
N3B C16B C17B 114.38(10) . . ?
N3B C16B H16C 108.7 . . ?
C17B C16B H16C 108.7 . . ?
N3B C16B H16D 108.7 . . ?
C17B C16B H16D 108.7 . . ?
H16C C16B H16D 107.6 . . ?
C22B C17B C18B 118.58(13) . . ?
C22B C17B C16B 119.14(13) . . ?
C18B C17B C16B 122.23(11) . . ?
C17B C18B C19B 120.64(15) . . ?
C17B C18B H18B 119.7 . . ?
C19B C18B H18B 119.7 . . ?
C20B C19B C18B 120.53(18) . . ?
C20B C19B H19B 119.7 . . ?
C18B C19B H19B 119.7 . . ?
C19B C20B C21B 119.62(15) . . ?
C19B C20B H20B 120.2 . . ?
C21B C20B H20B 120.2 . . ?
C20B C21B C22B 120.64(15) . . ?
C20B C21B H21B 119.7 . . ?
C22B C21B H21B 119.7 . . ?
C17B C22B C21B 119.98(17) . . ?
C17B C22B H22B 120.0 . . ?
C21B C22B H22B 120.0 . . ?

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
C8 N1 C1 O1 -10.18(18) . . . . ?
C8 N1 C1 C2 168.73(10) . . . . ?
O1 C1 C2 C7 13.88(16) . . . . ?
N1 C1 C2 C7 -165.12(10) . . . . ?
O1 C1 C2 C3 -168.20(11) . . . . ?
N1 C1 C2 C3 12.79(15) . . . . ?
C7 C2 C3 C4 -0.83(18) . . . . ?
C1 C2 C3 C4 -178.74(11) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C7 -0.7(2) . . . . ?
C5 C6 C7 C2 0.34(19) . . . . ?
C3 C2 C7 C6 0.45(18) . . . . ?
C1 C2 C7 C6 178.41(11) . . . . ?
C16 N3 C8 N1 -9.28(16) . . . . ?
C16 N3 C8 N2 171.80(10) . . . . ?
C1 N1 C8 N3 175.03(10) . . . . ?
C1 N1 C8 N2 -6.09(17) . . . . ?
C9 N2 C8 N3 7.81(18) . . . . ?
C9 N2 C8 N1 -171.05(11) . . . . ?
C8 N2 C9 C10 -138.18(12) . . . . ?
C8 N2 C9 C14 46.88(17) . . . . ?
C14 C9 C10 C11 0.37(17) . . . . ?
N2 C9 C10 C11 -174.73(10) . . . . ?
C9 C10 C11 C12 -0.10(18) . . . . ?
C10 C11 C12 C13 -0.31(17) . . . . ?
C10 C11 C12 C15 178.10(12) . . . . ?
C11 C12 C13 C14 0.45(17) . . . . ?
C15 C12 C13 C14 -177.97(11) . . . . ?
C12 C13 C14 C9 -0.19(17) . . . . ?
C10 C9 C14 C13 -0.22(16) . . . . ?
N2 C9 C14 C13 174.64(10) . . . . ?
C8 N3 C16 C17 95.32(13) . . . . ?
N3 C16 C17 C22 -20.12(17) . . . . ?
N3 C16 C17 C18 162.12(11) . . . . ?
C22 C17 C18 C19 -0.50(18) . . . . ?
C16 C17 C18 C19 177.38(11) . . . . ?
C17 C18 C19 C20 0.1(2) . . . . ?
C18 C19 C20 C21 0.4(2) . . . . ?
C19 C20 C21 C22 -0.6(2) . . . . ?
C18 C17 C22 C21 0.34(18) . . . . ?
C16 C17 C22 C21 -177.39(11) . . . . ?
C20 C21 C22 C17 0.2(2) . . . . ?
C8B N1B C1B O1B 1.65(17) . . . . ?
C8B N1B C1B C2B -178.41(9) . . . . ?
O1B C1B C2B C7B -21.25(15) . . . . ?
N1B C1B C2B C7B 158.80(10) . . . . ?
O1B C1B C2B C3B 156.70(11) . . . . ?
N1B C1B C2B C3B -23.25(15) . . . . ?
C7B C2B C3B C4B 1.21(17) . . . . ?
C1B C2B C3B C4B -176.72(10) . . . . ?
C2B C3B C4B C5B -1.34(18) . . . . ?
C3B C4B C5B C6B 0.15(19) . . . . ?
C4B C5B C6B C7B 1.1(2) . . . . ?
C5B C6B C7B C2B -1.27(19) . . . . ?
C3B C2B C7B C6B 0.09(17) . . . . ?
C1B C2B C7B C6B 178.11(11) . . . . ?
C16B N3B C8B N1B 7.12(16) . . . . ?
C16B N3B C8B N2B -172.44(10) . . . . ?
C1B N1B C8B N3B -177.53(10) . . . . ?
C1B N1B C8B N2B 2.02(16) . . . . ?
C9B N2B C8B N3B -7.30(17) . . . . ?
C9B N2B C8B N1B 173.16(10) . . . . ?
C8B N2B C9B C10B 139.50(12) . . . . ?
C8B N2B C9B C14B -46.14(18) . . . . ?
C14B C9B C10B C11B 0.79(19) . . . . ?
N2B C9B C10B C11B 175.34(11) . . . . ?
C9B C10B C11B C12B 0.1(2) . . . . ?
C10B C11B C12B C13B -0.9(2) . . . . ?
C10B C11B C12B C15B -179.88(13) . . . . ?
C11B C12B C13B C14B 0.72(19) . . . . ?
C15B C12B C13B C14B 179.75(13) . . . . ?
C12B C13B C14B C9B 0.16(19) . . . . ?
C10B C9B C14B C13B -0.92(18) . . . . ?
N2B C9B C14B C13B -175.18(11) . . . . ?
C8B N3B C16B C17B -97.00(13) . . . . ?
N3B C16B C17B C22B -157.74(12) . . . . ?
N3B C16B C17B C18B 25.07(17) . . . . ?
C22B C17B C18B C19B -0.4(2) . . . . ?
C16B C17B C18B C19B 176.82(13) . . . . ?
C17B C18B C19B C20B -0.5(2) . . . . ?
C18B C19B C20B C21B 0.7(3) . . . . ?
C19B C20B C21B C22B -0.1(2) . . . . ?
C18B C17B C22B C21B 1.0(2) . . . . ?
C16B C17B C22B C21B -176.27(12) . . . . ?
C20B C21B C22B C17B -0.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_rkb
_database_code_depnum_ccdc_archive 'CCDC 1023790'
_audit_update_record             
;
2014-09-11 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H36 Cu N6 O2'
_chemical_formula_weight         720.31

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.4363(13)
_cell_length_b                   10.3390(16)
_cell_length_c                   10.9129(17)
_cell_angle_alpha                65.535(2)
_cell_angle_beta                 86.346(2)
_cell_angle_gamma                85.211(2)
_cell_volume                     862.9(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9924
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.54

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             375
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8874
_exptl_absorpt_correction_T_max  0.9733
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'APEX II'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14794
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         27.50
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0
_reflns_number_total             3925
_reflns_number_gt                3815
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX-II (BRUKER-NONIUS, 2003)'
_computing_cell_refinement       
; 
  APEX-II(BRUKER-NONIUS, 2003) 
;
_computing_data_reduction        APEX-II
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    Olex2
_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)+(0.0255P)²+0.7181P] 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         3925
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0853
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
Cu1 Cu 0.5000 0.5000 0.0000 0.01335(9) Uani 1 2 d S . .
O1 O 0.48669(15) 0.37800(13) 0.18701(11) 0.0236(3) Uani 1 1 d . . .
N1 N 0.31730(15) 0.41069(13) -0.03078(12) 0.0141(2) Uani 1 1 d . . .
N2 N 0.28480(16) 0.23301(14) 0.19528(13) 0.0162(3) Uani 1 1 d . . .
N3 N 0.13202(16) 0.23733(14) 0.02960(13) 0.0172(3) Uani 1 1 d . . .
H3 H 0.0991 0.2781 -0.0536 0.021 Uiso 1 1 calc R . .
C1 C 0.25055(17) 0.29754(15) 0.06253(15) 0.0138(3) Uani 1 1 d . . .
C2 C 0.39096(18) 0.27998(15) 0.24748(15) 0.0145(3) Uani 1 1 d . . .
C3 C 0.24879(18) 0.46873(16) -0.16138(15) 0.0145(3) Uani 1 1 d . . .
C4 C 0.1353(2) 0.58294(17) -0.19401(16) 0.0200(3) Uani 1 1 d . . .
H4 H 0.1037 0.6211 -0.1300 0.024 Uiso 1 1 calc R . .
C5 C 0.0682(2) 0.64107(18) -0.32021(18) 0.0245(4) Uani 1 1 d . . .
H5 H -0.0086 0.7192 -0.3422 0.029 Uiso 1 1 calc R . .
C6 C 0.1130(2) 0.58555(19) -0.41393(16) 0.0239(4) Uani 1 1 d . . .
H6 H 0.0671 0.6256 -0.5001 0.029 Uiso 1 1 calc R . .
C7 C 0.2253(2) 0.47094(19) -0.38141(16) 0.0223(3) Uani 1 1 d . . .
H7 H 0.2555 0.4322 -0.4453 0.027 Uiso 1 1 calc R . .
C8 C 0.29360(19) 0.41286(17) -0.25556(16) 0.0179(3) Uani 1 1 d . . .
H8 H 0.3708 0.3350 -0.2339 0.021 Uiso 1 1 calc R . .
C9 C 0.05614(18) 0.11076(16) 0.12178(15) 0.0165(3) Uani 1 1 d . . .
H9A H -0.0559 0.1184 0.0963 0.020 Uiso 1 1 calc R . .
H9B H 0.0552 0.1081 0.2136 0.020 Uiso 1 1 calc R . .
C10 C 0.13423(18) -0.02865(16) 0.12585(15) 0.0151(3) Uani 1 1 d . . .
C11 C 0.27184(18) -0.03542(17) 0.05095(16) 0.0190(3) Uani 1 1 d . . .
H11 H 0.3209 0.0497 -0.0050 0.023 Uiso 1 1 calc R . .
C12 C 0.3384(2) -0.16585(19) 0.05709(18) 0.0235(3) Uani 1 1 d . . .
H12 H 0.4325 -0.1691 0.0055 0.028 Uiso 1 1 calc R . .
C13 C 0.2679(2) -0.29102(18) 0.13831(18) 0.0239(3) Uani 1 1 d . . .
H13 H 0.3139 -0.3800 0.1431 0.029 Uiso 1 1 calc R . .
C14 C 0.1295(2) -0.28531(17) 0.21252(17) 0.0220(3) Uani 1 1 d . . .
H14 H 0.0802 -0.3706 0.2677 0.026 Uiso 1 1 calc R . .
C15 C 0.06311(19) -0.15525(17) 0.20618(16) 0.0185(3) Uani 1 1 d . . .
H15 H -0.0317 -0.1523 0.2570 0.022 Uiso 1 1 calc R . .
C16 C 0.40057(18) 0.21008(16) 0.39762(15) 0.0152(3) Uani 1 1 d . . .
C17 C 0.30426(19) 0.09966(17) 0.47591(16) 0.0190(3) Uani 1 1 d . . .
H17 H 0.2297 0.0683 0.4341 0.023 Uiso 1 1 calc R . .
C18 C 0.3176(2) 0.03584(18) 0.61480(17) 0.0242(4) Uani 1 1 d . . .
H18 H 0.2519 -0.0391 0.6679 0.029 Uiso 1 1 calc R . .
C19 C 0.4266(2) 0.08095(19) 0.67643(16) 0.0253(4) Uani 1 1 d . . .
H19 H 0.4352 0.0369 0.7715 0.030 Uiso 1 1 calc R . .
C20 C 0.5228(2) 0.19003(19) 0.59952(17) 0.0254(4) Uani 1 1 d . . .
H20 H 0.5976 0.2207 0.6417 0.030 Uiso 1 1 calc R . .
C21 C 0.5096(2) 0.25454(18) 0.46052(16) 0.0207(3) Uani 1 1 d . . .
H21 H 0.5754 0.3296 0.4079 0.025 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
Cu1 O1 1.9055(11) . ?
Cu1 O1 1.9055(11) 2_665 ?
Cu1 N1 1.9752(13) 2_665 ?
Cu1 N1 1.9752(13) . ?
O1 C2 1.2765(18) . ?
N1 C1 1.3315(19) . ?
N1 C3 1.4367(19) . ?
N2 C2 1.315(2) . ?
N2 C1 1.3595(19) . ?
N3 C1 1.3607(19) . ?
N3 C9 1.4497(19) . ?
N3 H3 0.8800 . ?
C2 C16 1.497(2) . ?
C3 C8 1.392(2) . ?
C3 C4 1.394(2) . ?
C4 C5 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.391(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.518(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.391(2) . ?
C10 C15 1.398(2) . ?
C11 C12 1.394(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.393(2) . ?
C16 C17 1.397(2) . ?
C17 C18 1.388(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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
O1 Cu1 O1 180.0 . 2_665 ?
O1 Cu1 N1 90.31(5) . 2_665 ?
O1 Cu1 N1 89.69(5) 2_665 2_665 ?
O1 Cu1 N1 89.69(5) . . ?
O1 Cu1 N1 90.31(5) 2_665 . ?
N1 Cu1 N1 180.0 2_665 . ?
C2 O1 Cu1 128.05(10) . . ?
C1 N1 C3 116.12(12) . . ?
C1 N1 Cu1 124.39(10) . . ?
C3 N1 Cu1 119.49(9) . . ?
C2 N2 C1 122.07(13) . . ?
C1 N3 C9 124.66(13) . . ?
C1 N3 H3 117.7 . . ?
C9 N3 H3 117.7 . . ?
N1 C1 N2 126.61(14) . . ?
N1 C1 N3 120.23(13) . . ?
N2 C1 N3 113.13(13) . . ?
O1 C2 N2 128.55(14) . . ?
O1 C2 C16 115.55(13) . . ?
N2 C2 C16 115.90(13) . . ?
C8 C3 C4 119.56(14) . . ?
C8 C3 N1 121.18(14) . . ?
C4 C3 N1 119.26(14) . . ?
C5 C4 C3 120.10(15) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.32(16) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 119.76(15) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C8 120.19(15) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C3 120.07(15) . . ?
C7 C8 H8 120.0 . . ?
C3 C8 H8 120.0 . . ?
N3 C9 C10 115.00(13) . . ?
N3 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
N3 C9 H9B 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C11 C10 C15 118.60(15) . . ?
C11 C10 C9 122.73(14) . . ?
C15 C10 C9 118.66(14) . . ?
C10 C11 C12 120.66(15) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 120.27(15) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.53(16) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 120.14(15) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 120.78(15) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C21 C16 C17 119.27(14) . . ?
C21 C16 C2 119.31(14) . . ?
C17 C16 C2 121.41(14) . . ?
C18 C17 C16 119.95(15) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.30(16) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 120.09(15) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 119.85(16) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C16 120.53(16) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?

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
O1 Cu1 O1 C2 -147(24) 2_665 . . . ?
N1 Cu1 O1 C2 -177.98(14) 2_665 . . . ?
N1 Cu1 O1 C2 2.02(14) . . . . ?
O1 Cu1 N1 C1 -6.93(12) . . . . ?
O1 Cu1 N1 C1 173.07(12) 2_665 . . . ?
N1 Cu1 N1 C1 131(14) 2_665 . . . ?
O1 Cu1 N1 C3 173.13(11) . . . . ?
O1 Cu1 N1 C3 -6.87(11) 2_665 . . . ?
N1 Cu1 N1 C3 -49(14) 2_665 . . . ?
C3 N1 C1 N2 -173.45(14) . . . . ?
Cu1 N1 C1 N2 6.6(2) . . . . ?
C3 N1 C1 N3 4.5(2) . . . . ?
Cu1 N1 C1 N3 -175.46(10) . . . . ?
C2 N2 C1 N1 1.2(2) . . . . ?
C2 N2 C1 N3 -176.89(14) . . . . ?
C9 N3 C1 N1 177.26(13) . . . . ?
C9 N3 C1 N2 -4.5(2) . . . . ?
Cu1 O1 C2 N2 4.6(2) . . . . ?
Cu1 O1 C2 C16 -175.08(10) . . . . ?
C1 N2 C2 O1 -7.4(3) . . . . ?
C1 N2 C2 C16 172.28(13) . . . . ?
C1 N1 C3 C8 -84.16(18) . . . . ?
Cu1 N1 C3 C8 95.79(15) . . . . ?
C1 N1 C3 C4 95.77(17) . . . . ?
Cu1 N1 C3 C4 -84.29(16) . . . . ?
C8 C3 C4 C5 -0.4(2) . . . . ?
N1 C3 C4 C5 179.65(14) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C3 0.5(2) . . . . ?
C4 C3 C8 C7 0.0(2) . . . . ?
N1 C3 C8 C7 179.95(14) . . . . ?
C1 N3 C9 C10 -89.89(18) . . . . ?
N3 C9 C10 C11 2.4(2) . . . . ?
N3 C9 C10 C15 -176.28(13) . . . . ?
C15 C10 C11 C12 -0.7(2) . . . . ?
C9 C10 C11 C12 -179.44(15) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C10 -0.2(3) . . . . ?
C11 C10 C15 C14 0.8(2) . . . . ?
C9 C10 C15 C14 179.58(14) . . . . ?
O1 C2 C16 C21 0.0(2) . . . . ?
N2 C2 C16 C21 -179.66(14) . . . . ?
O1 C2 C16 C17 -178.95(14) . . . . ?
N2 C2 C16 C17 1.3(2) . . . . ?
C21 C16 C17 C18 0.2(2) . . . . ?
C2 C16 C17 C18 179.15(14) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C20 C21 C16 -0.2(3) . . . . ?
C17 C16 C21 C20 0.0(2) . . . . ?
C2 C16 C21 C20 -178.99(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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_rkb
_database_code_depnum_ccdc_archive 'CCDC 1023791'
_audit_update_record             
;
2014-09-11 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H40 Cu N6 O2'
_chemical_formula_weight         748.36

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.1250(8)
_cell_length_b                   11.5140(14)
_cell_length_c                   13.2365(16)
_cell_angle_alpha                81.520(2)
_cell_angle_beta                 87.731(2)
_cell_angle_gamma                85.984(2)
_cell_volume                     920.6(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.50

_exptl_crystal_description       column
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             391
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7616
_exptl_absorpt_correction_T_max  0.8773
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2006)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'APEX II'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19956
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         27.49
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0
_reflns_number_total             4161
_reflns_number_gt                4052
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX-II (BRUKER-NONIUS, 2003)'
_computing_cell_refinement       
; 
  APEX-II(BRUKER-NONIUS, 2003) 
;
_computing_data_reduction        APEX-II
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    Olex2
_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)+(0.0316P)²+0.4310P] 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         4161
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0684
_refine_ls_wR_factor_gt          0.0677
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
Cu1 Cu 0.0000 0.0000 0.0000 0.01554(7) Uani 1 2 d S . .
O1 O 0.04821(16) 0.03931(9) 0.13238(7) 0.0264(2) Uani 1 1 d . . .
N1 N -0.24853(17) -0.04506(9) 0.22390(8) 0.0197(2) Uani 1 1 d . . .
N2 N -0.45312(18) -0.18960(9) 0.18970(8) 0.0212(2) Uani 1 1 d . . .
H2 H -0.4962 -0.2370 0.1491 0.025 Uiso 1 1 calc R . .
N3 N -0.21084(16) -0.11292(9) 0.06029(8) 0.0172(2) Uani 1 1 d . . .
C1 C -0.0813(2) 0.02149(10) 0.21014(9) 0.0181(2) Uani 1 1 d . . .
C2 C -0.0357(2) 0.08342(10) 0.29826(9) 0.0197(2) Uani 1 1 d . . .
C3 C 0.1594(2) 0.13795(12) 0.29989(10) 0.0267(3) Uani 1 1 d . . .
H3 H 0.2630 0.1372 0.2446 0.032 Uiso 1 1 calc R . .
C4 C 0.2027(3) 0.19378(13) 0.38284(11) 0.0323(3) Uani 1 1 d . . .
H4 H 0.3371 0.2299 0.3844 0.039 Uiso 1 1 calc R . .
C5 C 0.0514(3) 0.19696(13) 0.46277(11) 0.0333(3) Uani 1 1 d . . .
H5 H 0.0814 0.2353 0.5190 0.040 Uiso 1 1 calc R . .
C6 C -0.1443(3) 0.14397(15) 0.46062(11) 0.0362(3) Uani 1 1 d . . .
H6 H -0.2494 0.1470 0.5151 0.043 Uiso 1 1 calc R . .
C7 C -0.1872(2) 0.08644(13) 0.37910(11) 0.0286(3) Uani 1 1 d . . .
H7 H -0.3205 0.0490 0.3785 0.034 Uiso 1 1 calc R . .
C8 C -0.29916(19) -0.11369(10) 0.15374(9) 0.0172(2) Uani 1 1 d . . .
C9 C -0.5508(2) -0.19650(12) 0.29258(10) 0.0245(3) Uani 1 1 d . . .
H9A H -0.6358 -0.1218 0.3002 0.029 Uiso 1 1 calc R . .
H9B H -0.4342 -0.2090 0.3435 0.029 Uiso 1 1 calc R . .
C10 C -0.6992(2) -0.29692(11) 0.31112(9) 0.0198(2) Uani 1 1 d . . .
C11 C -0.6595(2) -0.39122(13) 0.38761(10) 0.0277(3) Uani 1 1 d . . .
H11 H -0.5371 -0.3927 0.4298 0.033 Uiso 1 1 calc R . .
C12 C -0.7972(3) -0.48376(13) 0.40322(11) 0.0339(3) Uani 1 1 d . . .
H12 H -0.7688 -0.5477 0.4561 0.041 Uiso 1 1 calc R . .
C13 C -0.9748(2) -0.48291(13) 0.34217(12) 0.0322(3) Uani 1 1 d . . .
H13 H -1.0681 -0.5464 0.3525 0.039 Uiso 1 1 calc R . .
C14 C -1.0162(2) -0.38922(13) 0.26586(12) 0.0308(3) Uani 1 1 d . . .
H14 H -1.1387 -0.3881 0.2238 0.037 Uiso 1 1 calc R . .
C15 C -0.8792(2) -0.29655(12) 0.25045(11) 0.0258(3) Uani 1 1 d . . .
H15 H -0.9090 -0.2324 0.1979 0.031 Uiso 1 1 calc R . .
C16 C -0.28743(19) -0.19633(10) 0.00117(9) 0.0166(2) Uani 1 1 d . . .
C17 C -0.4922(2) -0.17792(11) -0.04216(10) 0.0213(2) Uani 1 1 d . . .
H17 H -0.5813 -0.1088 -0.0340 0.026 Uiso 1 1 calc R . .
C18 C -0.5675(2) -0.26000(12) -0.09745(10) 0.0241(3) Uani 1 1 d . . .
H18 H -0.7084 -0.2466 -0.1261 0.029 Uiso 1 1 calc R . .
C19 C -0.4400(2) -0.36146(12) -0.11154(10) 0.0248(3) Uani 1 1 d . . .
C20 C -0.2331(2) -0.37772(12) -0.07000(11) 0.0264(3) Uani 1 1 d . . .
H20 H -0.1419 -0.4454 -0.0803 0.032 Uiso 1 1 calc R . .
C21 C -0.1573(2) -0.29663(11) -0.01367(10) 0.0215(2) Uani 1 1 d . . .
H21 H -0.0161 -0.3099 0.0147 0.026 Uiso 1 1 calc R . .
C22 C -0.5245(3) -0.45110(15) -0.17027(13) 0.0394(4) Uani 1 1 d . . .
H22A H -0.5706 -0.5187 -0.1223 0.059 Uiso 1 1 calc R . .
H22B H -0.4080 -0.4773 -0.2163 0.059 Uiso 1 1 calc R . .
H22C H -0.6495 -0.4154 -0.2103 0.059 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
Cu1 O1 1.9122(9) . ?
Cu1 O1 1.9122(9) 2 ?
Cu1 N3 1.9602(10) . ?
Cu1 N3 1.9602(10) 2 ?
O1 C1 1.2755(15) . ?
N1 C1 1.3126(16) . ?
N1 C8 1.3625(15) . ?
N2 C8 1.3554(15) . ?
N2 C9 1.4592(15) . ?
N2 H2 0.8800 . ?
N3 C8 1.3293(15) . ?
N3 C16 1.4382(14) . ?
C1 C2 1.4987(16) . ?
C2 C3 1.3904(18) . ?
C2 C7 1.3914(18) . ?
C3 C4 1.3945(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.3892(19) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C10 1.5063(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3861(19) . ?
C10 C15 1.3887(18) . ?
C11 C12 1.391(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3900(19) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.3897(17) . ?
C16 C21 1.3906(17) . ?
C17 C18 1.3903(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.3907(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.391(2) . ?
C19 C22 1.5102(18) . ?
C20 C21 1.3918(17) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
O1 Cu1 O1 180.0 . 2 ?
O1 Cu1 N3 90.03(4) . . ?
O1 Cu1 N3 89.97(4) 2 . ?
O1 Cu1 N3 89.96(4) . 2 ?
O1 Cu1 N3 90.04(4) 2 2 ?
N3 Cu1 N3 180.0 . 2 ?
C1 O1 Cu1 125.59(8) . . ?
C1 N1 C8 121.95(10) . . ?
C8 N2 C9 123.12(10) . . ?
C8 N2 H2 118.4 . . ?
C9 N2 H2 118.4 . . ?
C8 N3 C16 116.37(10) . . ?
C8 N3 Cu1 123.25(8) . . ?
C16 N3 Cu1 120.29(7) . . ?
O1 C1 N1 128.63(11) . . ?
O1 C1 C2 115.93(11) . . ?
N1 C1 C2 115.43(11) . . ?
C3 C2 C7 119.52(12) . . ?
C3 C2 C1 120.09(11) . . ?
C7 C2 C1 120.39(11) . . ?
C2 C3 C4 119.87(13) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.42(13) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.77(13) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 120.20(14) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 120.21(13) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
N3 C8 N2 120.85(11) . . ?
N3 C8 N1 126.68(11) . . ?
N2 C8 N1 112.45(10) . . ?
N2 C9 C10 109.49(10) . . ?
N2 C9 H9A 109.8 . . ?
C10 C9 H9A 109.8 . . ?
N2 C9 H9B 109.8 . . ?
C10 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C11 C10 C15 118.70(12) . . ?
C11 C10 C9 121.35(12) . . ?
C15 C10 C9 119.95(12) . . ?
C10 C11 C12 120.65(13) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 120.21(13) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.63(13) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.19(13) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.62(12) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C21 118.96(11) . . ?
C17 C16 N3 120.60(11) . . ?
C21 C16 N3 120.44(11) . . ?
C16 C17 C18 120.40(12) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C19 121.12(12) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C20 C19 C18 118.06(12) . . ?
C20 C19 C22 121.17(13) . . ?
C18 C19 C22 120.77(13) . . ?
C19 C20 C21 121.21(12) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C16 C21 C20 120.21(12) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
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 . . ?

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
O1 Cu1 O1 C1 -95(11) 2 . . . ?
N3 Cu1 O1 C1 -20.42(11) . . . . ?
N3 Cu1 O1 C1 159.58(11) 2 . . . ?
O1 Cu1 N3 C8 15.90(10) . . . . ?
O1 Cu1 N3 C8 -164.10(10) 2 . . . ?
N3 Cu1 N3 C8 -18.9(18) 2 . . . ?
O1 Cu1 N3 C16 -167.72(9) . . . . ?
O1 Cu1 N3 C16 12.28(9) 2 . . . ?
N3 Cu1 N3 C16 157.5(18) 2 . . . ?
Cu1 O1 C1 N1 14.2(2) . . . . ?
Cu1 O1 C1 C2 -166.58(8) . . . . ?
C8 N1 C1 O1 4.3(2) . . . . ?
C8 N1 C1 C2 -174.83(11) . . . . ?
O1 C1 C2 C3 -11.33(18) . . . . ?
N1 C1 C2 C3 167.96(12) . . . . ?
O1 C1 C2 C7 168.93(12) . . . . ?
N1 C1 C2 C7 -11.79(18) . . . . ?
C7 C2 C3 C4 0.8(2) . . . . ?
C1 C2 C3 C4 -178.94(13) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C2 -1.1(2) . . . . ?
C3 C2 C7 C6 0.3(2) . . . . ?
C1 C2 C7 C6 -179.98(13) . . . . ?
C16 N3 C8 N2 -0.12(17) . . . . ?
Cu1 N3 C8 N2 176.40(9) . . . . ?
C16 N3 C8 N1 178.30(11) . . . . ?
Cu1 N3 C8 N1 -5.18(18) . . . . ?
C9 N2 C8 N3 178.20(12) . . . . ?
C9 N2 C8 N1 -0.43(17) . . . . ?
C1 N1 C8 N3 -8.9(2) . . . . ?
C1 N1 C8 N2 169.66(11) . . . . ?
C8 N2 C9 C10 -174.76(11) . . . . ?
N2 C9 C10 C11 118.29(14) . . . . ?
N2 C9 C10 C15 -61.26(16) . . . . ?
C15 C10 C11 C12 0.1(2) . . . . ?
C9 C10 C11 C12 -179.48(13) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C12 C13 C14 -0.5(2) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C11 C10 C15 C14 -0.3(2) . . . . ?
C9 C10 C15 C14 179.27(13) . . . . ?
C13 C14 C15 C10 0.1(2) . . . . ?
C8 N3 C16 C17 75.03(15) . . . . ?
Cu1 N3 C16 C17 -101.59(12) . . . . ?
C8 N3 C16 C21 -105.10(13) . . . . ?
Cu1 N3 C16 C21 78.28(13) . . . . ?
C21 C16 C17 C18 1.48(18) . . . . ?
N3 C16 C17 C18 -178.65(11) . . . . ?
C16 C17 C18 C19 -0.6(2) . . . . ?
C17 C18 C19 C20 -1.0(2) . . . . ?
C17 C18 C19 C22 179.02(13) . . . . ?
C18 C19 C20 C21 1.6(2) . . . . ?
C22 C19 C20 C21 -178.36(13) . . . . ?
C17 C16 C21 C20 -0.83(19) . . . . ?
N3 C16 C21 C20 179.30(11) . . . . ?
C19 C20 C21 C16 -0.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.046
