# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_erk6444
_database_code_depnum_ccdc_archive 'CCDC 1008256'
_audit_update_record             
;
2014-06-13 deposited with the CCDC.
2015-04-23 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 H25 N3'
_chemical_formula_weight         319.44

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'

_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                   11.8867(3)
_cell_length_b                   12.5284(6)
_cell_length_c                   13.0514(4)
_cell_angle_alpha                79.096(4)
_cell_angle_beta                 89.444(2)
_cell_angle_gamma                77.230(5)
_cell_volume                     1860.29(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    5664
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8266
_exptl_absorpt_correction_T_max  0.9259
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(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  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21856
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.45
_diffrn_reflns_theta_max         67.02
_reflns_number_total             6335
_reflns_number_gt                5970
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The hydrogens at N4A and N4B atoms were refined freely, but with N-H 
 distance restraints (SADI).
;

_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)+(0.0549P)²+0.4229P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   'at N1 from difmap, others geom'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6335
_refine_ls_number_parameters     441
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
N4A N 0.64584(12) 0.76417(13) 0.42831(10) 0.0610(3) Uani 1 1 d D . .
H01A H 0.6832(16) 0.8050(16) 0.3796(15) 0.077(6) Uiso 1 1 d D . .
N1A N 0.35088(9) 0.73300(9) 0.28109(9) 0.0477(3) Uani 1 1 d . . .
N3A N 0.52298(9) 0.79866(9) 0.27745(8) 0.0394(2) Uani 1 1 d . . .
C4A C 0.55459(11) 0.75497(11) 0.38333(10) 0.0437(3) Uani 1 1 d . . .
C5A C 0.47283(12) 0.69467(11) 0.43956(11) 0.0455(3) Uani 1 1 d . . .
C6A C 0.49233(14) 0.64481(12) 0.54484(12) 0.0565(4) Uani 1 1 d . . .
H6A H 0.5570 0.6522 0.5816 0.068 Uiso 1 1 calc R . .
C7A C 0.41673(17) 0.58477(14) 0.59497(14) 0.0686(5) Uani 1 1 d . . .
H7A H 0.4297 0.5516 0.6660 0.082 Uiso 1 1 calc R . .
C8A C 0.32201(16) 0.57332(14) 0.54105(15) 0.0705(5) Uani 1 1 d . . .
H8A H 0.2717 0.5311 0.5754 0.085 Uiso 1 1 calc R . .
C9A C 0.30068(14) 0.62278(13) 0.43838(14) 0.0608(4) Uani 1 1 d . . .
H9A H 0.2352 0.6154 0.4029 0.073 Uiso 1 1 calc R . .
C10A C 0.37635(12) 0.68468(11) 0.38566(11) 0.0466(3) Uani 1 1 d . . .
C2A C 0.42232(11) 0.78679(10) 0.23203(10) 0.0416(3) Uani 1 1 d . . .
C11A C 0.39609(13) 0.84154(13) 0.12051(11) 0.0524(3) Uani 1 1 d . . .
H11A H 0.3243 0.8272 0.0978 0.079 Uiso 1 1 calc R . .
H11B H 0.4581 0.8117 0.0779 0.079 Uiso 1 1 calc R . .
H11C H 0.3888 0.9213 0.1133 0.079 Uiso 1 1 calc R . .
C21A C 0.60012(10) 0.85765(10) 0.21480(10) 0.0387(3) Uani 1 1 d . . .
C22A C 0.69055(11) 0.79606(11) 0.16588(10) 0.0418(3) Uani 1 1 d . . .
C23A C 0.76361(11) 0.85472(12) 0.10636(10) 0.0457(3) Uani 1 1 d . . .
H23A H 0.8247 0.8161 0.0719 0.055 Uiso 1 1 calc R . .
C24A C 0.74711(11) 0.96857(12) 0.09752(11) 0.0466(3) Uani 1 1 d . . .
H24A H 0.7974 1.0066 0.0575 0.056 Uiso 1 1 calc R . .
C25A C 0.65772(12) 1.02728(11) 0.14668(11) 0.0455(3) Uani 1 1 d . . .
H25A H 0.6480 1.1048 0.1400 0.055 Uiso 1 1 calc R . .
C26A C 0.58143(11) 0.97306(11) 0.20630(10) 0.0409(3) Uani 1 1 d . . .
C27A C 0.71145(13) 0.67091(12) 0.17465(12) 0.0534(4) Uani 1 1 d . . .
H27A H 0.6483 0.6451 0.2150 0.064 Uiso 1 1 calc R . .
C28A C 0.70956(19) 0.63856(15) 0.06747(16) 0.0778(5) Uani 1 1 d . . .
H28A H 0.6365 0.6757 0.0311 0.117 Uiso 1 1 calc R . .
H28B H 0.7188 0.5584 0.0762 0.117 Uiso 1 1 calc R . .
H28C H 0.7722 0.6611 0.0271 0.117 Uiso 1 1 calc R . .
C29A C 0.82513(17) 0.61206(15) 0.23372(17) 0.0801(5) Uani 1 1 d . . .
H29A H 0.8248 0.6325 0.3018 0.120 Uiso 1 1 calc R . .
H29B H 0.8887 0.6343 0.1946 0.120 Uiso 1 1 calc R . .
H29C H 0.8341 0.5320 0.2423 0.120 Uiso 1 1 calc R . .
C30A C 0.48299(12) 1.04004(11) 0.25895(11) 0.0470(3) Uani 1 1 d . . .
H30A H 0.4315 0.9900 0.2870 0.056 Uiso 1 1 calc R . .
C31A C 0.52811(15) 1.07971(17) 0.35017(15) 0.0706(5) Uani 1 1 d . . .
H31A H 0.5733 1.0163 0.3980 0.106 Uiso 1 1 calc R . .
H31B H 0.4636 1.1166 0.3862 0.106 Uiso 1 1 calc R . .
H31C H 0.5762 1.1316 0.3245 0.106 Uiso 1 1 calc R . .
C32A C 0.41155(16) 1.13829(14) 0.18136(15) 0.0723(5) Uani 1 1 d . . .
H32A H 0.3498 1.1791 0.2175 0.108 Uiso 1 1 calc R . .
H32B H 0.3789 1.1106 0.1266 0.108 Uiso 1 1 calc R . .
H32C H 0.4607 1.1874 0.1509 0.108 Uiso 1 1 calc R . .
N4B N -0.04178(11) 0.76489(13) 0.92439(10) 0.0630(4) Uani 1 1 d D . .
H01B H -0.0994(16) 0.8040(16) 0.8762(15) 0.081(6) Uiso 1 1 d D . .
N1B N 0.27282(9) 0.73261(9) 0.77964(9) 0.0445(3) Uani 1 1 d . . .
N3B N 0.06960(9) 0.79435(9) 0.77321(8) 0.0399(2) Uani 1 1 d . . .
C4B C 0.05516(11) 0.75421(11) 0.87958(10) 0.0441(3) Uani 1 1 d . . .
C5B C 0.16340(11) 0.69785(11) 0.93801(10) 0.0427(3) Uani 1 1 d . . .
C6B C 0.16449(13) 0.65264(12) 1.04444(11) 0.0529(3) Uani 1 1 d . . .
H6B H 0.0946 0.6566 1.0794 0.063 Uiso 1 1 calc R . .
C7B C 0.26721(15) 0.60233(13) 1.09839(12) 0.0587(4) Uani 1 1 d . . .
H7B H 0.2675 0.5721 1.1700 0.070 Uiso 1 1 calc R . .
C8B C 0.37056(14) 0.59630(12) 1.04685(13) 0.0569(4) Uani 1 1 d . . .
H8B H 0.4407 0.5627 1.0841 0.068 Uiso 1 1 calc R . .
C9B C 0.37098(12) 0.63898(11) 0.94226(12) 0.0511(3) Uani 1 1 d . . .
H9B H 0.4414 0.6337 0.9080 0.061 Uiso 1 1 calc R . .
C10B C 0.26730(11) 0.69043(10) 0.88578(11) 0.0420(3) Uani 1 1 d . . .
C2B C 0.17718(11) 0.78170(10) 0.72875(10) 0.0413(3) Uani 1 1 d . . .
C11B C 0.18043(12) 0.82967(13) 0.61541(11) 0.0537(4) Uani 1 1 d . . .
H11D H 0.2596 0.8155 0.5934 0.080 Uiso 1 1 calc R . .
H11E H 0.1488 0.9095 0.6035 0.080 Uiso 1 1 calc R . .
H11F H 0.1350 0.7953 0.5756 0.080 Uiso 1 1 calc R . .
C21B C -0.03323(10) 0.85324(11) 0.71007(10) 0.0402(3) Uani 1 1 d . . .
C22B C -0.09442(11) 0.79163(11) 0.66180(10) 0.0438(3) Uani 1 1 d . . .
C23B C -0.19392(12) 0.85040(13) 0.60308(11) 0.0485(3) Uani 1 1 d . . .
H23B H -0.2366 0.8118 0.5690 0.058 Uiso 1 1 calc R . .
C24B C -0.23053(12) 0.96408(13) 0.59432(11) 0.0494(3) Uani 1 1 d . . .
H24B H -0.2983 1.0020 0.5550 0.059 Uiso 1 1 calc R . .
C25B C -0.16875(11) 1.02305(12) 0.64269(11) 0.0473(3) Uani 1 1 d . . .
H25B H -0.1950 1.1006 0.6360 0.057 Uiso 1 1 calc R . .
C26B C -0.06805(11) 0.96907(11) 0.70130(10) 0.0423(3) Uani 1 1 d . . .
C27B C -0.05658(13) 0.66618(12) 0.67204(12) 0.0528(3) Uani 1 1 d . . .
H27B H 0.0194 0.6420 0.7097 0.063 Uiso 1 1 calc R . .
C28B C -0.1402(2) 0.60697(16) 0.7364(2) 0.0933(7) Uani 1 1 d . . .
H28D H -0.1482 0.6293 0.8038 0.140 Uiso 1 1 calc R . .
H28E H -0.1108 0.5269 0.7463 0.140 Uiso 1 1 calc R . .
H28F H -0.2149 0.6270 0.7000 0.140 Uiso 1 1 calc R . .
C29B C -0.0414(2) 0.63138(17) 0.56645(16) 0.0840(6) Uani 1 1 d . . .
H29D H 0.0128 0.6690 0.5268 0.126 Uiso 1 1 calc R . .
H29E H -0.1152 0.6516 0.5286 0.126 Uiso 1 1 calc R . .
H29F H -0.0121 0.5513 0.5765 0.126 Uiso 1 1 calc R . .
C30B C -0.00080(12) 1.03582(12) 0.75295(11) 0.0484(3) Uani 1 1 d . . .
H30B H 0.0737 0.9857 0.7802 0.058 Uiso 1 1 calc R . .
C31B C 0.02571(18) 1.13383(15) 0.67478(16) 0.0757(5) Uani 1 1 d . . .
H31D H 0.0684 1.1746 0.7102 0.114 Uiso 1 1 calc R . .
H31E H -0.0460 1.1830 0.6450 0.114 Uiso 1 1 calc R . .
H31F H 0.0715 1.1060 0.6196 0.114 Uiso 1 1 calc R . .
C32B C -0.06478(15) 1.07584(17) 0.84484(15) 0.0722(5) Uani 1 1 d . . .
H32D H -0.0808 1.0125 0.8933 0.108 Uiso 1 1 calc R . .
H32E H -0.1368 1.1277 0.8199 0.108 Uiso 1 1 calc R . .
H32F H -0.0176 1.1129 0.8800 0.108 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
N4A C4A 1.2757(19) . ?
N4A H01A 0.914(17) . ?
N1A C2A 1.2901(17) . ?
N1A C10A 1.3911(19) . ?
N3A C2A 1.3897(16) . ?
N3A C4A 1.4083(17) . ?
N3A C21A 1.4533(15) . ?
C4A C5A 1.4679(19) . ?
C5A C10A 1.392(2) . ?
C5A C6A 1.396(2) . ?
C6A C7A 1.379(2) . ?
C6A H6A 0.9400 . ?
C7A C8A 1.381(3) . ?
C7A H7A 0.9400 . ?
C8A C9A 1.366(3) . ?
C8A H8A 0.9400 . ?
C9A C10A 1.406(2) . ?
C9A H9A 0.9400 . ?
C2A C11A 1.4908(19) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C11A H11C 0.9700 . ?
C21A C26A 1.3965(18) . ?
C21A C22A 1.4017(18) . ?
C22A C23A 1.3967(18) . ?
C22A C27A 1.5145(19) . ?
C23A C24A 1.379(2) . ?
C23A H23A 0.9400 . ?
C24A C25A 1.3790(19) . ?
C24A H24A 0.9400 . ?
C25A C26A 1.3956(18) . ?
C25A H25A 0.9400 . ?
C26A C30A 1.5211(18) . ?
C27A C29A 1.526(2) . ?
C27A C28A 1.530(2) . ?
C27A H27A 0.9900 . ?
C28A H28A 0.9700 . ?
C28A H28B 0.9700 . ?
C28A H28C 0.9700 . ?
C29A H29A 0.9700 . ?
C29A H29B 0.9700 . ?
C29A H29C 0.9700 . ?
C30A C31A 1.519(2) . ?
C30A C32A 1.531(2) . ?
C30A H30A 0.9900 . ?
C31A H31A 0.9700 . ?
C31A H31B 0.9700 . ?
C31A H31C 0.9700 . ?
C32A H32A 0.9700 . ?
C32A H32B 0.9700 . ?
C32A H32C 0.9700 . ?
N4B C4B 1.2790(18) . ?
N4B H01B 0.920(17) . ?
N1B C2B 1.2894(17) . ?
N1B C10B 1.3926(18) . ?
N3B C2B 1.3886(16) . ?
N3B C4B 1.4067(17) . ?
N3B C21B 1.4520(16) . ?
C4B C5B 1.4660(19) . ?
C5B C6B 1.396(2) . ?
C5B C10B 1.3984(19) . ?
C6B C7B 1.376(2) . ?
C6B H6B 0.9400 . ?
C7B C8B 1.389(2) . ?
C7B H7B 0.9400 . ?
C8B C9B 1.369(2) . ?
C8B H8B 0.9400 . ?
C9B C10B 1.4015(19) . ?
C9B H9B 0.9400 . ?
C2B C11B 1.4913(19) . ?
C11B H11D 0.9700 . ?
C11B H11E 0.9700 . ?
C11B H11F 0.9700 . ?
C21B C26B 1.4010(19) . ?
C21B C22B 1.4010(19) . ?
C22B C23B 1.3955(19) . ?
C22B C27B 1.516(2) . ?
C23B C24B 1.377(2) . ?
C23B H23B 0.9400 . ?
C24B C25B 1.382(2) . ?
C24B H24B 0.9400 . ?
C25B C26B 1.3927(19) . ?
C25B H25B 0.9400 . ?
C26B C30B 1.5206(19) . ?
C27B C29B 1.520(2) . ?
C27B C28B 1.523(2) . ?
C27B H27B 0.9900 . ?
C28B H28D 0.9700 . ?
C28B H28E 0.9700 . ?
C28B H28F 0.9700 . ?
C29B H29D 0.9700 . ?
C29B H29E 0.9700 . ?
C29B H29F 0.9700 . ?
C30B C32B 1.520(2) . ?
C30B C31B 1.529(2) . ?
C30B H30B 0.9900 . ?
C31B H31D 0.9700 . ?
C31B H31E 0.9700 . ?
C31B H31F 0.9700 . ?
C32B H32D 0.9700 . ?
C32B H32E 0.9700 . ?
C32B H32F 0.9700 . ?

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
C4A N4A H01A 107.0(12) . . ?
C2A N1A C10A 117.79(12) . . ?
C2A N3A C4A 122.47(11) . . ?
C2A N3A C21A 119.79(10) . . ?
C4A N3A C21A 117.73(10) . . ?
N4A C4A N3A 124.59(13) . . ?
N4A C4A C5A 121.63(13) . . ?
N3A C4A C5A 113.77(12) . . ?
C10A C5A C6A 119.89(13) . . ?
C10A C5A C4A 119.07(12) . . ?
C6A C5A C4A 121.02(14) . . ?
C7A C6A C5A 119.99(17) . . ?
C7A C6A H6A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C6A C7A C8A 120.12(16) . . ?
C6A C7A H7A 119.9 . . ?
C8A C7A H7A 119.9 . . ?
C9A C8A C7A 120.70(15) . . ?
C9A C8A H8A 119.7 . . ?
C7A C8A H8A 119.7 . . ?
C8A C9A C10A 120.21(17) . . ?
C8A C9A H9A 119.9 . . ?
C10A C9A H9A 119.9 . . ?
N1A C10A C5A 123.02(12) . . ?
N1A C10A C9A 117.91(14) . . ?
C5A C10A C9A 119.07(14) . . ?
N1A C2A N3A 123.81(12) . . ?
N1A C2A C11A 119.03(12) . . ?
N3A C2A C11A 117.15(11) . . ?
C2A C11A H11A 109.5 . . ?
C2A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C2A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C26A C21A C22A 122.80(11) . . ?
C26A C21A N3A 118.68(11) . . ?
C22A C21A N3A 118.52(11) . . ?
C23A C22A C21A 117.37(12) . . ?
C23A C22A C27A 119.47(12) . . ?
C21A C22A C27A 123.16(12) . . ?
C24A C23A C22A 120.74(12) . . ?
C24A C23A H23A 119.6 . . ?
C22A C23A H23A 119.6 . . ?
C23A C24A C25A 120.81(12) . . ?
C23A C24A H24A 119.6 . . ?
C25A C24A H24A 119.6 . . ?
C24A C25A C26A 120.87(12) . . ?
C24A C25A H25A 119.6 . . ?
C26A C25A H25A 119.6 . . ?
C25A C26A C21A 117.40(12) . . ?
C25A C26A C30A 119.76(12) . . ?
C21A C26A C30A 122.84(11) . . ?
C22A C27A C29A 111.04(13) . . ?
C22A C27A C28A 111.73(13) . . ?
C29A C27A C28A 110.30(15) . . ?
C22A C27A H27A 107.9 . . ?
C29A C27A H27A 107.9 . . ?
C28A C27A H27A 107.9 . . ?
C27A C28A H28A 109.5 . . ?
C27A C28A H28B 109.5 . . ?
H28A C28A H28B 109.5 . . ?
C27A C28A H28C 109.5 . . ?
H28A C28A H28C 109.5 . . ?
H28B C28A H28C 109.5 . . ?
C27A C29A H29A 109.5 . . ?
C27A C29A H29B 109.5 . . ?
H29A C29A H29B 109.5 . . ?
C27A C29A H29C 109.5 . . ?
H29A C29A H29C 109.5 . . ?
H29B C29A H29C 109.5 . . ?
C31A C30A C26A 110.84(12) . . ?
C31A C30A C32A 110.90(14) . . ?
C26A C30A C32A 111.67(12) . . ?
C31A C30A H30A 107.7 . . ?
C26A C30A H30A 107.7 . . ?
C32A C30A H30A 107.7 . . ?
C30A C31A H31A 109.5 . . ?
C30A C31A H31B 109.5 . . ?
H31A C31A H31B 109.5 . . ?
C30A C31A H31C 109.5 . . ?
H31A C31A H31C 109.5 . . ?
H31B C31A H31C 109.5 . . ?
C30A C32A H32A 109.5 . . ?
C30A C32A H32B 109.5 . . ?
H32A C32A H32B 109.5 . . ?
C30A C32A H32C 109.5 . . ?
H32A C32A H32C 109.5 . . ?
H32B C32A H32C 109.5 . . ?
C4B N4B H01B 109.0(13) . . ?
C2B N1B C10B 117.67(11) . . ?
C2B N3B C4B 122.51(11) . . ?
C2B N3B C21B 120.06(10) . . ?
C4B N3B C21B 117.41(10) . . ?
N4B C4B N3B 124.86(13) . . ?
N4B C4B C5B 121.27(13) . . ?
N3B C4B C5B 113.88(11) . . ?
C6B C5B C10B 119.71(13) . . ?
C6B C5B C4B 121.28(12) . . ?
C10B C5B C4B 119.00(12) . . ?
C7B C6B C5B 120.38(14) . . ?
C7B C6B H6B 119.8 . . ?
C5B C6B H6B 119.8 . . ?
C6B C7B C8B 119.92(14) . . ?
C6B C7B H7B 120.0 . . ?
C8B C7B H7B 120.0 . . ?
C9B C8B C7B 120.47(14) . . ?
C9B C8B H8B 119.8 . . ?
C7B C8B H8B 119.8 . . ?
C8B C9B C10B 120.54(14) . . ?
C8B C9B H9B 119.7 . . ?
C10B C9B H9B 119.7 . . ?
N1B C10B C5B 122.91(12) . . ?
N1B C10B C9B 118.12(12) . . ?
C5B C10B C9B 118.97(13) . . ?
N1B C2B N3B 124.02(12) . . ?
N1B C2B C11B 118.95(11) . . ?
N3B C2B C11B 117.02(11) . . ?
C2B C11B H11D 109.5 . . ?
C2B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C2B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C26B C21B C22B 122.77(12) . . ?
C26B C21B N3B 118.60(11) . . ?
C22B C21B N3B 118.62(12) . . ?
C23B C22B C21B 117.24(13) . . ?
C23B C22B C27B 120.25(13) . . ?
C21B C22B C27B 122.51(12) . . ?
C24B C23B C22B 121.01(13) . . ?
C24B C23B H23B 119.5 . . ?
C22B C23B H23B 119.5 . . ?
C23B C24B C25B 120.70(13) . . ?
C23B C24B H24B 119.7 . . ?
C25B C24B H24B 119.7 . . ?
C24B C25B C26B 120.86(13) . . ?
C24B C25B H25B 119.6 . . ?
C26B C25B H25B 119.6 . . ?
C25B C26B C21B 117.41(12) . . ?
C25B C26B C30B 119.95(12) . . ?
C21B C26B C30B 122.64(12) . . ?
C22B C27B C29B 112.15(13) . . ?
C22B C27B C28B 111.24(13) . . ?
C29B C27B C28B 110.45(16) . . ?
C22B C27B H27B 107.6 . . ?
C29B C27B H27B 107.6 . . ?
C28B C27B H27B 107.6 . . ?
C27B C28B H28D 109.5 . . ?
C27B C28B H28E 109.5 . . ?
H28D C28B H28E 109.5 . . ?
C27B C28B H28F 109.5 . . ?
H28D C28B H28F 109.5 . . ?
H28E C28B H28F 109.5 . . ?
C27B C29B H29D 109.5 . . ?
C27B C29B H29E 109.5 . . ?
H29D C29B H29E 109.5 . . ?
C27B C29B H29F 109.5 . . ?
H29D C29B H29F 109.5 . . ?
H29E C29B H29F 109.5 . . ?
C32B C30B C26B 110.94(12) . . ?
C32B C30B C31B 110.82(14) . . ?
C26B C30B C31B 111.58(13) . . ?
C32B C30B H30B 107.8 . . ?
C26B C30B H30B 107.8 . . ?
C31B C30B H30B 107.8 . . ?
C30B C31B H31D 109.5 . . ?
C30B C31B H31E 109.5 . . ?
H31D C31B H31E 109.5 . . ?
C30B C31B H31F 109.5 . . ?
H31D C31B H31F 109.5 . . ?
H31E C31B H31F 109.5 . . ?
C30B C32B H32D 109.5 . . ?
C30B C32B H32E 109.5 . . ?
H32D C32B H32E 109.5 . . ?
C30B C32B H32F 109.5 . . ?
H32D C32B H32F 109.5 . . ?
H32E C32B H32F 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
C2A N3A C4A N4A -179.77(13) . . . . ?
C21A N3A C4A N4A 0.5(2) . . . . ?
C2A N3A C4A C5A 1.09(17) . . . . ?
C21A N3A C4A C5A -178.66(10) . . . . ?
N4A C4A C5A C10A -178.21(14) . . . . ?
N3A C4A C5A C10A 0.95(17) . . . . ?
N4A C4A C5A C6A -0.1(2) . . . . ?
N3A C4A C5A C6A 179.05(12) . . . . ?
C10A C5A C6A C7A 0.7(2) . . . . ?
C4A C5A C6A C7A -177.39(13) . . . . ?
C5A C6A C7A C8A 0.4(2) . . . . ?
C6A C7A C8A C9A -1.2(2) . . . . ?
C7A C8A C9A C10A 1.1(2) . . . . ?
C2A N1A C10A C5A 1.91(19) . . . . ?
C2A N1A C10A C9A -177.88(12) . . . . ?
C6A C5A C10A N1A 179.36(12) . . . . ?
C4A C5A C10A N1A -2.52(19) . . . . ?
C6A C5A C10A C9A -0.86(19) . . . . ?
C4A C5A C10A C9A 177.26(12) . . . . ?
C8A C9A C10A N1A 179.78(13) . . . . ?
C8A C9A C10A C5A 0.0(2) . . . . ?
C10A N1A C2A N3A 0.29(19) . . . . ?
C10A N1A C2A C11A -178.71(12) . . . . ?
C4A N3A C2A N1A -1.83(19) . . . . ?
C21A N3A C2A N1A 177.91(12) . . . . ?
C4A N3A C2A C11A 177.19(12) . . . . ?
C21A N3A C2A C11A -3.06(17) . . . . ?
C2A N3A C21A C26A 88.15(15) . . . . ?
C4A N3A C21A C26A -92.10(14) . . . . ?
C2A N3A C21A C22A -92.18(14) . . . . ?
C4A N3A C21A C22A 87.58(14) . . . . ?
C26A C21A C22A C23A -0.18(19) . . . . ?
N3A C21A C22A C23A -179.84(11) . . . . ?
C26A C21A C22A C27A -179.99(13) . . . . ?
N3A C21A C22A C27A 0.35(19) . . . . ?
C21A C22A C23A C24A 0.60(19) . . . . ?
C27A C22A C23A C24A -179.59(13) . . . . ?
C22A C23A C24A C25A -0.4(2) . . . . ?
C23A C24A C25A C26A -0.2(2) . . . . ?
C24A C25A C26A C21A 0.6(2) . . . . ?
C24A C25A C26A C30A -179.49(12) . . . . ?
C22A C21A C26A C25A -0.43(19) . . . . ?
N3A C21A C26A C25A 179.23(11) . . . . ?
C22A C21A C26A C30A 179.71(12) . . . . ?
N3A C21A C26A C30A -0.63(18) . . . . ?
C23A C22A C27A C29A 66.20(18) . . . . ?
C21A C22A C27A C29A -114.00(16) . . . . ?
C23A C22A C27A C28A -57.41(18) . . . . ?
C21A C22A C27A C28A 122.40(15) . . . . ?
C25A C26A C30A C31A -71.76(17) . . . . ?
C21A C26A C30A C31A 108.10(15) . . . . ?
C25A C26A C30A C32A 52.44(18) . . . . ?
C21A C26A C30A C32A -127.70(15) . . . . ?
C2B N3B C4B N4B 179.16(14) . . . . ?
C21B N3B C4B N4B 0.7(2) . . . . ?
C2B N3B C4B C5B -0.34(18) . . . . ?
C21B N3B C4B C5B -178.83(11) . . . . ?
N4B C4B C5B C6B 0.7(2) . . . . ?
N3B C4B C5B C6B -179.73(12) . . . . ?
N4B C4B C5B C10B -178.68(14) . . . . ?
N3B C4B C5B C10B 0.84(18) . . . . ?
C10B C5B C6B C7B 0.9(2) . . . . ?
C4B C5B C6B C7B -178.50(13) . . . . ?
C5B C6B C7B C8B 0.0(2) . . . . ?
C6B C7B C8B C9B -0.7(2) . . . . ?
C7B C8B C9B C10B 0.7(2) . . . . ?
C2B N1B C10B C5B 0.92(19) . . . . ?
C2B N1B C10B C9B -178.69(12) . . . . ?
C6B C5B C10B N1B 179.38(12) . . . . ?
C4B C5B C10B N1B -1.18(19) . . . . ?
C6B C5B C10B C9B -1.01(19) . . . . ?
C4B C5B C10B C9B 178.43(12) . . . . ?
C8B C9B C10B N1B 179.86(12) . . . . ?
C8B C9B C10B C5B 0.2(2) . . . . ?
C10B N1B C2B N3B -0.37(19) . . . . ?
C10B N1B C2B C11B 178.85(12) . . . . ?
C4B N3B C2B N1B 0.1(2) . . . . ?
C21B N3B C2B N1B 178.56(12) . . . . ?
C4B N3B C2B C11B -179.11(12) . . . . ?
C21B N3B C2B C11B -0.66(18) . . . . ?
C2B N3B C21B C26B -88.31(15) . . . . ?
C4B N3B C21B C26B 90.21(14) . . . . ?
C2B N3B C21B C22B 92.65(14) . . . . ?
C4B N3B C21B C22B -88.83(14) . . . . ?
C26B C21B C22B C23B -0.04(19) . . . . ?
N3B C21B C22B C23B 178.96(11) . . . . ?
C26B C21B C22B C27B -179.69(12) . . . . ?
N3B C21B C22B C27B -0.70(18) . . . . ?
C21B C22B C23B C24B -0.71(19) . . . . ?
C27B C22B C23B C24B 178.95(13) . . . . ?
C22B C23B C24B C25B 0.7(2) . . . . ?
C23B C24B C25B C26B 0.1(2) . . . . ?
C24B C25B C26B C21B -0.77(19) . . . . ?
C24B C25B C26B C30B 179.39(12) . . . . ?
C22B C21B C26B C25B 0.76(19) . . . . ?
N3B C21B C26B C25B -178.23(11) . . . . ?
C22B C21B C26B C30B -179.40(12) . . . . ?
N3B C21B C26B C30B 1.60(18) . . . . ?
C23B C22B C27B C29B 55.81(19) . . . . ?
C21B C22B C27B C29B -124.54(16) . . . . ?
C23B C22B C27B C28B -68.45(19) . . . . ?
C21B C22B C27B C28B 111.19(17) . . . . ?
C25B C26B C30B C32B 71.76(17) . . . . ?
C21B C26B C30B C32B -108.07(16) . . . . ?
C25B C26B C30B C31B -52.34(18) . . . . ?
C21B C26B C30B C31B 127.83(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.955
_diffrn_reflns_theta_full        67.02
_diffrn_measured_fraction_theta_full 0.955
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.028
####################################################################### 
# 
# 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_erk7412
_database_code_depnum_ccdc_archive 'CCDC 1008257'
_audit_update_record             
;
2014-06-13 deposited with the CCDC.
2015-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H27 N3'
_chemical_formula_weight         381.51

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'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   P-4

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

_cell_length_a                   16.4490(8)
_cell_length_b                   16.4490(8)
_cell_length_c                   8.4714(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2292.10(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2409
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8934
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(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  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8679
_diffrn_reflns_av_R_equivalents  0.058
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.80
_diffrn_reflns_theta_max         67.45
_reflns_number_total             3410
_reflns_number_gt                2945
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The hydrogen at N3 atom were refined freely, but with N-H distance 
 restraints (DFIX and U-fixed value).
 A badly half disordered dichloromethane molecule was found in the 
 asymmetrical unit and could not be satisfactorily refined. The program 
 SQUEEZE (A. L. Spek J. Appl. Cryst., 2003, 36, 7-13) was therefore used to
 remove mathematically the effect of the solvent. 
 The quoted formula and derived parameters are not included the squeezed
 solvent molecule. 
;

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.500 -0.002 208 25 ' '
2 0.000 0.500 0.330 16 0 ' '
3 0.500 0.000 0.670 16 0 ' '


_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)+(0.0925P)²+0.7740P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(9)
_refine_ls_number_reflns         3410
_refine_ls_number_parameters     269
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1621
_refine_ls_wR_factor_gt          0.1527
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
N3 N 0.33159(14) 0.83448(14) 0.1758(3) 0.0306(6) Uani 1 1 d . . .
N1 N 0.37459(16) 0.71001(15) 0.2896(3) 0.0373(6) Uani 1 1 d . . .
N4 N 0.41542(18) 0.94966(17) 0.1727(4) 0.0494(7) Uani 1 1 d D . .
H01 H 0.382(2) 0.979(2) 0.107(4) 0.059 Uiso 1 1 d D . .
C2 C 0.32299(19) 0.75151(17) 0.2081(4) 0.0320(7) Uani 1 1 d . . .
C10 C 0.44223(18) 0.74944(19) 0.3517(4) 0.0341(7) Uani 1 1 d . . .
C9 C 0.4965(2) 0.7046(2) 0.4440(4) 0.0452(8) Uani 1 1 d . . .
H9 H 0.4863 0.6492 0.4626 0.054 Uiso 1 1 calc R . .
C8 C 0.5641(2) 0.7397(2) 0.5074(5) 0.0491(9) Uani 1 1 d . . .
H8 H 0.6001 0.7088 0.5693 0.059 Uiso 1 1 calc R . .
C5 C 0.45807(18) 0.83156(18) 0.3229(4) 0.0333(7) Uani 1 1 d . . .
C7 C 0.5792(2) 0.8214(2) 0.4801(4) 0.0473(9) Uani 1 1 d . . .
H7 H 0.6255 0.8459 0.5243 0.057 Uiso 1 1 calc R . .
C6 C 0.52746(19) 0.8670(2) 0.3892(4) 0.0428(8) Uani 1 1 d . . .
H6 H 0.5386 0.9223 0.3715 0.051 Uiso 1 1 calc R . .
C4 C 0.40271(18) 0.87709(18) 0.2217(4) 0.0335(7) Uani 1 1 d . . .
C21 C 0.27338(18) 0.87769(17) 0.0788(4) 0.0316(7) Uani 1 1 d . . .
C22 C 0.21874(18) 0.93082(17) 0.1513(4) 0.0326(7) Uani 1 1 d . . .
C23 C 0.1637(2) 0.9714(2) 0.0539(4) 0.0416(8) Uani 1 1 d . . .
H23 H 0.1262 1.0077 0.0993 0.050 Uiso 1 1 calc R . .
C24 C 0.1629(2) 0.9597(2) -0.1065(4) 0.0454(8) Uani 1 1 d . . .
H24 H 0.1247 0.9873 -0.1694 0.054 Uiso 1 1 calc R . .
C25 C 0.2180(2) 0.9076(2) -0.1754(4) 0.0456(8) Uani 1 1 d . . .
H25 H 0.2167 0.8999 -0.2854 0.055 Uiso 1 1 calc R . .
C26 C 0.27569(19) 0.86594(19) -0.0852(4) 0.0379(7) Uani 1 1 d . . .
C27 C 0.2175(2) 0.9471(2) 0.3280(4) 0.0402(8) Uani 1 1 d . . .
H27 H 0.2547 0.9079 0.3795 0.048 Uiso 1 1 calc R . .
C28 C 0.2481(3) 1.0329(3) 0.3630(6) 0.0654(12) Uani 1 1 d . . .
H28A H 0.2091 1.0723 0.3242 0.098 Uiso 1 1 calc R . .
H28B H 0.3000 1.0413 0.3111 0.098 Uiso 1 1 calc R . .
H28C H 0.2547 1.0396 0.4761 0.098 Uiso 1 1 calc R . .
C29 C 0.1333(2) 0.9355(2) 0.3979(4) 0.0514(9) Uani 1 1 d . . .
H29A H 0.0958 0.9737 0.3496 0.077 Uiso 1 1 calc R . .
H29B H 0.1353 0.9450 0.5108 0.077 Uiso 1 1 calc R . .
H29C H 0.1149 0.8804 0.3779 0.077 Uiso 1 1 calc R . .
C30 C 0.3385(2) 0.8149(2) -0.1684(4) 0.0505(9) Uani 1 1 d . . .
H30 H 0.3684 0.7839 -0.0868 0.061 Uiso 1 1 calc R . .
C31 C 0.3992(3) 0.8693(3) -0.2513(6) 0.0729(13) Uani 1 1 d . . .
H31A H 0.3715 0.9009 -0.3316 0.109 Uiso 1 1 calc R . .
H31B H 0.4409 0.8361 -0.3004 0.109 Uiso 1 1 calc R . .
H31C H 0.4240 0.9056 -0.1752 0.109 Uiso 1 1 calc R . .
C32 C 0.3010(3) 0.7531(3) -0.2832(6) 0.0731(13) Uani 1 1 d . . .
H32A H 0.2586 0.7227 -0.2297 0.110 Uiso 1 1 calc R . .
H32B H 0.3428 0.7160 -0.3197 0.110 Uiso 1 1 calc R . .
H32C H 0.2778 0.7816 -0.3728 0.110 Uiso 1 1 calc R . .
C11 C 0.25432(19) 0.70467(19) 0.1412(4) 0.0366(7) Uani 1 1 d . . .
C12 C 0.1730(2) 0.7266(2) 0.1509(5) 0.0495(9) Uani 1 1 d . . .
H12 H 0.1584 0.7768 0.1960 0.059 Uiso 1 1 calc R . .
C13 C 0.1135(2) 0.6751(2) 0.0947(7) 0.0672(13) Uani 1 1 d . . .
H13 H 0.0586 0.6905 0.1021 0.081 Uiso 1 1 calc R . .
C14 C 0.1331(3) 0.6024(2) 0.0287(7) 0.0741(15) Uani 1 1 d . . .
H14 H 0.0920 0.5679 -0.0092 0.089 Uiso 1 1 calc R . .
C15 C 0.2137(3) 0.5793(2) 0.0173(6) 0.0661(12) Uani 1 1 d . . .
H15 H 0.2278 0.5294 -0.0292 0.079 Uiso 1 1 calc R . .
C16 C 0.2727(2) 0.6300(2) 0.0747(5) 0.0526(9) Uani 1 1 d . . .
H16 H 0.3274 0.6137 0.0687 0.063 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
N3 C2 1.399(4) . ?
N3 C4 1.418(4) . ?
N3 C21 1.448(4) . ?
N1 C2 1.290(4) . ?
N1 C10 1.391(4) . ?
N4 C4 1.281(4) . ?
N4 H01 0.925(19) . ?
C2 C11 1.480(4) . ?
C10 C5 1.397(4) . ?
C10 C9 1.398(4) . ?
C9 C8 1.362(5) . ?
C9 H9 0.9400 . ?
C8 C7 1.386(5) . ?
C8 H8 0.9400 . ?
C5 C6 1.399(4) . ?
C5 C4 1.457(4) . ?
C7 C6 1.370(5) . ?
C7 H7 0.9400 . ?
C6 H6 0.9400 . ?
C21 C22 1.396(4) . ?
C21 C26 1.404(4) . ?
C22 C23 1.395(4) . ?
C22 C27 1.520(4) . ?
C23 C24 1.373(5) . ?
C23 H23 0.9400 . ?
C24 C25 1.377(5) . ?
C24 H24 0.9400 . ?
C25 C26 1.398(5) . ?
C25 H25 0.9400 . ?
C26 C30 1.506(5) . ?
C27 C29 1.519(5) . ?
C27 C28 1.528(5) . ?
C27 H27 0.9900 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 H28C 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 H29C 0.9700 . ?
C30 C31 1.512(6) . ?
C30 C32 1.537(6) . ?
C30 H30 0.9900 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 H31C 0.9700 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 H32C 0.9700 . ?
C11 C16 1.384(5) . ?
C11 C12 1.388(5) . ?
C12 C13 1.380(5) . ?
C12 H12 0.9400 . ?
C13 C14 1.359(6) . ?
C13 H13 0.9400 . ?
C14 C15 1.382(6) . ?
C14 H14 0.9400 . ?
C15 C16 1.369(5) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N3 C4 120.8(2) . . ?
C2 N3 C21 121.5(2) . . ?
C4 N3 C21 117.3(2) . . ?
C2 N1 C10 118.8(3) . . ?
C4 N4 H01 126(3) . . ?
N1 C2 N3 123.7(3) . . ?
N1 C2 C11 115.6(3) . . ?
N3 C2 C11 120.7(3) . . ?
N1 C10 C5 122.3(3) . . ?
N1 C10 C9 118.5(3) . . ?
C5 C10 C9 119.2(3) . . ?
C8 C9 C10 121.2(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C5 C6 119.0(3) . . ?
C10 C5 C4 118.9(3) . . ?
C6 C5 C4 122.1(3) . . ?
C6 C7 C8 120.8(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N4 C4 N3 120.4(3) . . ?
N4 C4 C5 124.6(3) . . ?
N3 C4 C5 115.0(3) . . ?
C22 C21 C26 122.6(3) . . ?
C22 C21 N3 118.9(3) . . ?
C26 C21 N3 118.4(3) . . ?
C23 C22 C21 117.2(3) . . ?
C23 C22 C27 119.3(3) . . ?
C21 C22 C27 123.5(3) . . ?
C24 C23 C22 121.6(3) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 C24 C25 120.1(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C26 121.3(3) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C25 C26 C21 117.1(3) . . ?
C25 C26 C30 118.9(3) . . ?
C21 C26 C30 123.9(3) . . ?
C29 C27 C22 112.0(3) . . ?
C29 C27 C28 109.9(3) . . ?
C22 C27 C28 110.4(3) . . ?
C29 C27 H27 108.1 . . ?
C22 C27 H27 108.1 . . ?
C28 C27 H27 108.1 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C26 C30 C31 109.9(3) . . ?
C26 C30 C32 112.9(3) . . ?
C31 C30 C32 111.2(4) . . ?
C26 C30 H30 107.5 . . ?
C31 C30 H30 107.5 . . ?
C32 C30 H30 107.5 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C16 C11 C12 117.7(3) . . ?
C16 C11 C2 116.8(3) . . ?
C12 C11 C2 125.3(3) . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.9(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 119.9(4) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 119.2(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C11 122.0(4) . . ?
C15 C16 H16 119.0 . . ?
C11 C16 H16 119.0 . . ?

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
C10 N1 C2 N3 1.0(5) . . . . ?
C10 N1 C2 C11 177.8(3) . . . . ?
C4 N3 C2 N1 5.2(5) . . . . ?
C21 N3 C2 N1 177.7(3) . . . . ?
C4 N3 C2 C11 -171.5(3) . . . . ?
C21 N3 C2 C11 1.1(4) . . . . ?
C2 N1 C10 C5 -2.9(4) . . . . ?
C2 N1 C10 C9 178.0(3) . . . . ?
N1 C10 C9 C8 179.7(3) . . . . ?
C5 C10 C9 C8 0.7(5) . . . . ?
C10 C9 C8 C7 0.0(6) . . . . ?
N1 C10 C5 C6 -179.9(3) . . . . ?
C9 C10 C5 C6 -0.9(5) . . . . ?
N1 C10 C5 C4 -1.2(4) . . . . ?
C9 C10 C5 C4 177.8(3) . . . . ?
C9 C8 C7 C6 -0.4(6) . . . . ?
C8 C7 C6 C5 0.2(5) . . . . ?
C10 C5 C6 C7 0.5(5) . . . . ?
C4 C5 C6 C7 -178.1(3) . . . . ?
C2 N3 C4 N4 170.0(3) . . . . ?
C21 N3 C4 N4 -2.8(4) . . . . ?
C2 N3 C4 C5 -8.8(4) . . . . ?
C21 N3 C4 C5 178.3(3) . . . . ?
C10 C5 C4 N4 -171.9(3) . . . . ?
C6 C5 C4 N4 6.7(5) . . . . ?
C10 C5 C4 N3 6.9(4) . . . . ?
C6 C5 C4 N3 -174.5(3) . . . . ?
C2 N3 C21 C22 106.1(3) . . . . ?
C4 N3 C21 C22 -81.1(3) . . . . ?
C2 N3 C21 C26 -75.5(4) . . . . ?
C4 N3 C21 C26 97.3(3) . . . . ?
C26 C21 C22 C23 1.6(4) . . . . ?
N3 C21 C22 C23 179.9(3) . . . . ?
C26 C21 C22 C27 -177.4(3) . . . . ?
N3 C21 C22 C27 0.9(4) . . . . ?
C21 C22 C23 C24 0.1(5) . . . . ?
C27 C22 C23 C24 179.2(3) . . . . ?
C22 C23 C24 C25 -0.8(5) . . . . ?
C23 C24 C25 C26 -0.3(5) . . . . ?
C24 C25 C26 C21 1.9(5) . . . . ?
C24 C25 C26 C30 -175.2(3) . . . . ?
C22 C21 C26 C25 -2.6(5) . . . . ?
N3 C21 C26 C25 179.1(3) . . . . ?
C22 C21 C26 C30 174.3(3) . . . . ?
N3 C21 C26 C30 -4.0(5) . . . . ?
C23 C22 C27 C29 53.2(4) . . . . ?
C21 C22 C27 C29 -127.8(3) . . . . ?
C23 C22 C27 C28 -69.7(4) . . . . ?
C21 C22 C27 C28 109.3(3) . . . . ?
C25 C26 C30 C31 71.6(4) . . . . ?
C21 C26 C30 C31 -105.3(4) . . . . ?
C25 C26 C30 C32 -53.2(5) . . . . ?
C21 C26 C30 C32 129.9(4) . . . . ?
N1 C2 C11 C16 -42.9(4) . . . . ?
N3 C2 C11 C16 134.0(3) . . . . ?
N1 C2 C11 C12 131.8(4) . . . . ?
N3 C2 C11 C12 -51.3(5) . . . . ?
C16 C11 C12 C13 -0.4(6) . . . . ?
C2 C11 C12 C13 -175.0(4) . . . . ?
C11 C12 C13 C14 -0.2(7) . . . . ?
C12 C13 C14 C15 0.0(8) . . . . ?
C13 C14 C15 C16 0.7(8) . . . . ?
C14 C15 C16 C11 -1.3(7) . . . . ?
C12 C11 C16 C15 1.1(6) . . . . ?
C2 C11 C16 C15 176.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 N1 0.94 2.57 3.501(4) 173.2 3_566
C14 H14 N4 0.94 2.73 3.479(5) 136.8 3_465

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        67.45
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.041
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_erk7434
_database_code_depnum_ccdc_archive 'CCDC 1008258'
_audit_update_record             
;
2014-06-13 deposited with the CCDC.
2015-04-23 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 H17 N3 O'
_chemical_formula_weight         327.38

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                   12.9137(5)
_cell_length_b                   14.1902(4)
_cell_length_c                   14.6060(6)
_cell_angle_alpha                107.781(2)
_cell_angle_beta                 90.352(2)
_cell_angle_gamma                98.594(2)
_cell_volume                     2516.23(16)
_cell_formula_units_Z            6
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    8057
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7813
_exptl_absorpt_correction_T_max  0.9745
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(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  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            34337
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         67.52
_reflns_number_total             8764
_reflns_number_gt                7650
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The hydrogens at N4A, N4B and N4C atoms were refined freely.
;

_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)+(0.0517P)²+0.4312P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8764
_refine_ls_number_parameters     691
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1046
_refine_ls_wR_factor_gt          0.1002
_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
N1A N 0.61229(8) 0.49015(8) 0.60263(8) 0.0465(3) Uani 1 1 d . . .
N3A N 0.73307(8) 0.45613(8) 0.70693(8) 0.0472(3) Uani 1 1 d . . .
N4A N 0.90225(12) 0.42185(15) 0.65611(12) 0.0829(5) Uani 1 1 d . . .
H01A H 0.9085(18) 0.4176(17) 0.7152(17) 0.104(7) Uiso 1 1 d . . .
O1A O 0.86416(10) 0.45538(10) 1.07109(8) 0.0738(3) Uani 1 1 d . . .
C2A C 0.63826(10) 0.48152(9) 0.68501(9) 0.0435(3) Uani 1 1 d . . .
C4A C 0.81212(11) 0.44079(11) 0.63945(10) 0.0537(3) Uani 1 1 d . . .
C5A C 0.78314(10) 0.45033(10) 0.54624(10) 0.0478(3) Uani 1 1 d . . .
C6A C 0.85374(12) 0.43786(11) 0.47290(10) 0.0557(3) Uani 1 1 d . . .
H6A H 0.9204 0.4228 0.4834 0.067 Uiso 1 1 calc R . .
C7A C 0.82610(13) 0.44745(11) 0.38582(11) 0.0592(4) Uani 1 1 d . . .
H7A H 0.8741 0.4398 0.3370 0.071 Uiso 1 1 calc R . .
C8A C 0.72711(12) 0.46842(11) 0.36964(10) 0.0565(4) Uani 1 1 d . . .
H8A H 0.7080 0.4735 0.3093 0.068 Uiso 1 1 calc R . .
C9A C 0.65690(11) 0.48185(10) 0.44122(10) 0.0505(3) Uani 1 1 d . . .
H9A H 0.5902 0.4964 0.4298 0.061 Uiso 1 1 calc R . .
C10A C 0.68470(10) 0.47390(9) 0.53109(9) 0.0448(3) Uani 1 1 d . . .
C11A C 0.56109(10) 0.50157(10) 0.76111(9) 0.0462(3) Uani 1 1 d . . .
C12A C 0.52254(11) 0.59144(11) 0.78291(10) 0.0546(3) Uani 1 1 d . . .
H12A H 0.5469 0.6385 0.7514 0.066 Uiso 1 1 calc R . .
C13A C 0.44836(13) 0.61201(14) 0.85087(12) 0.0682(4) Uani 1 1 d . . .
H13A H 0.4227 0.6732 0.8657 0.082 Uiso 1 1 calc R . .
C14A C 0.41193(14) 0.54350(16) 0.89680(13) 0.0767(5) Uani 1 1 d . . .
H14A H 0.3619 0.5581 0.9435 0.092 Uiso 1 1 calc R . .
C15A C 0.44866(14) 0.45318(14) 0.87452(13) 0.0748(5) Uani 1 1 d . . .
H15A H 0.4227 0.4058 0.9053 0.090 Uiso 1 1 calc R . .
C16A C 0.52348(12) 0.43207(12) 0.80714(11) 0.0597(4) Uani 1 1 d . . .
H16A H 0.5489 0.3707 0.7925 0.072 Uiso 1 1 calc R . .
C21A C 0.76214(10) 0.45813(10) 0.80339(9) 0.0471(3) Uani 1 1 d . . .
C22A C 0.76316(12) 0.36894(11) 0.82361(11) 0.0574(4) Uani 1 1 d . . .
H22A H 0.7405 0.3073 0.7760 0.069 Uiso 1 1 calc R . .
C23A C 0.79751(13) 0.37117(12) 0.91376(11) 0.0615(4) Uani 1 1 d . . .
H23A H 0.7978 0.3108 0.9277 0.074 Uiso 1 1 calc R . .
C24A C 0.83175(11) 0.46207(12) 0.98430(10) 0.0556(3) Uani 1 1 d . . .
C25A C 0.82983(11) 0.55125(11) 0.96422(10) 0.0547(3) Uani 1 1 d . . .
H25A H 0.8519 0.6130 1.0118 0.066 Uiso 1 1 calc R . .
C26A C 0.79500(11) 0.54824(10) 0.87326(10) 0.0501(3) Uani 1 1 d . . .
H26A H 0.7938 0.6084 0.8592 0.060 Uiso 1 1 calc R . .
C27A C 0.89836(18) 0.54681(18) 1.14538(13) 0.0898(6) Uani 1 1 d . . .
H27A H 0.9569 0.5850 1.1244 0.135 Uiso 1 1 calc R . .
H27B H 0.9203 0.5325 1.2027 0.135 Uiso 1 1 calc R . .
H27C H 0.8412 0.5854 1.1597 0.135 Uiso 1 1 calc R . .
N1B N 0.73865(8) 0.80598(9) 0.24855(8) 0.0472(3) Uani 1 1 d . . .
N3B N 0.61581(8) 0.82725(8) 0.37015(7) 0.0416(2) Uani 1 1 d . . .
N4B N 0.43727(9) 0.83249(10) 0.33530(9) 0.0544(3) Uani 1 1 d . . .
H01B H 0.4343(16) 0.8319(15) 0.3973(15) 0.090(6) Uiso 1 1 d . . .
O1B O 0.50835(8) 0.81505(7) 0.73610(7) 0.0546(2) Uani 1 1 d . . .
C2B C 0.71458(10) 0.81470(9) 0.33591(9) 0.0419(3) Uani 1 1 d . . .
C4B C 0.53124(10) 0.82913(9) 0.30947(9) 0.0432(3) Uani 1 1 d . . .
C5B C 0.55989(10) 0.82597(9) 0.21207(9) 0.0434(3) Uani 1 1 d . . .
C6B C 0.48576(11) 0.83300(11) 0.14526(10) 0.0528(3) Uani 1 1 d . . .
H6B H 0.4167 0.8397 0.1629 0.063 Uiso 1 1 calc R . .
C7B C 0.51350(13) 0.83017(13) 0.05428(11) 0.0622(4) Uani 1 1 d . . .
H7B H 0.4638 0.8364 0.0100 0.075 Uiso 1 1 calc R . .
C8B C 0.61497(13) 0.81812(13) 0.02702(11) 0.0632(4) Uani 1 1 d . . .
H8B H 0.6333 0.8158 -0.0357 0.076 Uiso 1 1 calc R . .
C9B C 0.68846(12) 0.80955(12) 0.09104(10) 0.0557(3) Uani 1 1 d . . .
H9B H 0.7567 0.8009 0.0720 0.067 Uiso 1 1 calc R . .
C10B C 0.66171(10) 0.81375(10) 0.18488(9) 0.0450(3) Uani 1 1 d . . .
C11B C 0.79843(10) 0.81119(10) 0.40480(9) 0.0430(3) Uani 1 1 d . . .
C12B C 0.83669(12) 0.72276(11) 0.39265(10) 0.0537(3) Uani 1 1 d . . .
H12B H 0.8074 0.6649 0.3430 0.064 Uiso 1 1 calc R . .
C13B C 0.91769(12) 0.71842(12) 0.45265(12) 0.0608(4) Uani 1 1 d . . .
H13B H 0.9429 0.6576 0.4439 0.073 Uiso 1 1 calc R . .
C14B C 0.96131(11) 0.80239(12) 0.52478(11) 0.0566(4) Uani 1 1 d . . .
H14B H 1.0161 0.7993 0.5660 0.068 Uiso 1 1 calc R . .
C15B C 0.92462(13) 0.89116(12) 0.53667(12) 0.0641(4) Uani 1 1 d . . .
H15B H 0.9552 0.9491 0.5856 0.077 Uiso 1 1 calc R . .
C16B C 0.84317(12) 0.89603(11) 0.47730(11) 0.0586(4) Uani 1 1 d . . .
H16B H 0.8182 0.9570 0.4862 0.070 Uiso 1 1 calc R . .
C21B C 0.59251(9) 0.82678(9) 0.46671(9) 0.0414(3) Uani 1 1 d . . .
C22B C 0.58643(10) 0.91536(9) 0.53810(9) 0.0447(3) Uani 1 1 d . . .
H22B H 0.6009 0.9765 0.5245 0.054 Uiso 1 1 calc R . .
C23B C 0.55910(10) 0.91509(10) 0.62976(9) 0.0457(3) Uani 1 1 d . . .
H23B H 0.5552 0.9756 0.6782 0.055 Uiso 1 1 calc R . .
C24B C 0.53751(10) 0.82429(10) 0.64922(9) 0.0443(3) Uani 1 1 d . . .
C25B C 0.54423(11) 0.73521(10) 0.57701(10) 0.0490(3) Uani 1 1 d . . .
H25B H 0.5306 0.6739 0.5904 0.059 Uiso 1 1 calc R . .
C26B C 0.57067(10) 0.73636(10) 0.48608(9) 0.0461(3) Uani 1 1 d . . .
H26B H 0.5739 0.6759 0.4373 0.055 Uiso 1 1 calc R . .
C27B C 0.49671(12) 0.90421(12) 0.81121(10) 0.0592(4) Uani 1 1 d . . .
H27D H 0.5645 0.9464 0.8299 0.089 Uiso 1 1 calc R . .
H27E H 0.4685 0.8867 0.8663 0.089 Uiso 1 1 calc R . .
H27F H 0.4492 0.9401 0.7885 0.089 Uiso 1 1 calc R . .
N1C N 0.97492(8) 0.81135(8) 0.03348(8) 0.0463(3) Uani 1 1 d . . .
N3C N 1.11670(8) 0.86311(8) -0.05169(7) 0.0432(2) Uani 1 1 d . . .
N4C N 1.28283(9) 0.94355(11) 0.02818(10) 0.0609(3) Uani 1 1 d . . .
H01C H 1.2959(14) 0.9471(14) -0.0346(14) 0.076(5) Uiso 1 1 d . . .
O1C O 1.23516(9) 0.90844(8) -0.40436(7) 0.0618(3) Uani 1 1 d . . .
C2C C 1.01332(10) 0.82240(9) -0.04454(9) 0.0423(3) Uani 1 1 d . . .
C4C C 1.18888(10) 0.89992(10) 0.02897(9) 0.0453(3) Uani 1 1 d . . .
C5C C 1.14670(10) 0.88420(9) 0.11694(9) 0.0435(3) Uani 1 1 d . . .
C6C C 1.20956(11) 0.91257(11) 0.20205(10) 0.0530(3) Uani 1 1 d . . .
H6C H 1.2794 0.9437 0.2035 0.064 Uiso 1 1 calc R . .
C7C C 1.17037(12) 0.89535(12) 0.28340(11) 0.0594(4) Uani 1 1 d . . .
H7C H 1.2136 0.9135 0.3400 0.071 Uiso 1 1 calc R . .
C8C C 1.06676(12) 0.85105(12) 0.28231(11) 0.0581(4) Uani 1 1 d . . .
H8C H 1.0402 0.8391 0.3382 0.070 Uiso 1 1 calc R . .
C9C C 1.00271(11) 0.82455(11) 0.19996(10) 0.0515(3) Uani 1 1 d . . .
H9C H 0.9323 0.7958 0.2002 0.062 Uiso 1 1 calc R . .
C10C C 1.04210(10) 0.84025(9) 0.11589(9) 0.0436(3) Uani 1 1 d . . .
C11C C 0.94183(10) 0.79192(10) -0.13280(9) 0.0455(3) Uani 1 1 d . . .
C12C C 0.85291(11) 0.83631(12) -0.12999(11) 0.0573(4) Uani 1 1 d . . .
H12C H 0.8388 0.8849 -0.0733 0.069 Uiso 1 1 calc R . .
C13C C 0.78483(13) 0.80925(15) -0.21046(13) 0.0736(5) Uani 1 1 d . . .
H13C H 0.7250 0.8401 -0.2084 0.088 Uiso 1 1 calc R . .
C14C C 0.80408(14) 0.73759(16) -0.29340(12) 0.0752(5) Uani 1 1 d . . .
H14C H 0.7578 0.7199 -0.3480 0.090 Uiso 1 1 calc R . .
C15C C 0.89075(13) 0.69206(13) -0.29619(11) 0.0660(4) Uani 1 1 d . . .
H15C H 0.9035 0.6426 -0.3527 0.079 Uiso 1 1 calc R . .
C16C C 0.95983(11) 0.71846(11) -0.21616(10) 0.0535(3) Uani 1 1 d . . .
H16C H 1.0189 0.6865 -0.2184 0.064 Uiso 1 1 calc R . .
C21C C 1.15170(9) 0.87570(9) -0.14186(9) 0.0429(3) Uani 1 1 d . . .
C22C C 1.21031(10) 0.80939(10) -0.19916(10) 0.0469(3) Uani 1 1 d . . .
H22C H 1.2301 0.7580 -0.1781 0.056 Uiso 1 1 calc R . .
C23C C 1.24039(10) 0.81786(10) -0.28767(10) 0.0487(3) Uani 1 1 d . . .
H23C H 1.2801 0.7723 -0.3268 0.058 Uiso 1 1 calc R . .
C24C C 1.21125(10) 0.89421(10) -0.31781(10) 0.0473(3) Uani 1 1 d . . .
C25C C 1.15430(11) 0.96231(10) -0.25921(10) 0.0522(3) Uani 1 1 d . . .
H25C H 1.1354 1.0145 -0.2796 0.063 Uiso 1 1 calc R . .
C26C C 1.12532(11) 0.95356(10) -0.17107(10) 0.0491(3) Uani 1 1 d . . .
H26C H 1.0877 1.0004 -0.1309 0.059 Uiso 1 1 calc R . .
C27C C 1.26840(14) 0.82789(14) -0.47611(11) 0.0667(4) Uani 1 1 d . . .
H27M H 1.3366 0.8177 -0.4562 0.100 Uiso 1 1 calc R . .
H27N H 1.2733 0.8435 -0.5363 0.100 Uiso 1 1 calc R . .
H27O H 1.2181 0.7674 -0.4849 0.100 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
N1A C2A 1.2932(17) . ?
N1A C10A 1.3961(17) . ?
N3A C2A 1.3889(17) . ?
N3A C4A 1.4173(17) . ?
N3A C21A 1.4466(17) . ?
N4A C4A 1.2712(19) . ?
N4A H01A 0.89(2) . ?
O1A C24A 1.3675(18) . ?
O1A C27A 1.421(2) . ?
C2A C11A 1.4882(18) . ?
C4A C5A 1.461(2) . ?
C5A C10A 1.3949(19) . ?
C5A C6A 1.3980(19) . ?
C6A C7A 1.370(2) . ?
C6A H6A 0.9400 . ?
C7A C8A 1.390(2) . ?
C7A H7A 0.9400 . ?
C8A C9A 1.376(2) . ?
C8A H8A 0.9400 . ?
C9A C10A 1.4005(19) . ?
C9A H9A 0.9400 . ?
C11A C12A 1.385(2) . ?
C11A C16A 1.388(2) . ?
C12A C13A 1.381(2) . ?
C12A H12A 0.9400 . ?
C13A C14A 1.372(3) . ?
C13A H13A 0.9400 . ?
C14A C15A 1.379(3) . ?
C14A H14A 0.9400 . ?
C15A C16A 1.382(2) . ?
C15A H15A 0.9400 . ?
C16A H16A 0.9400 . ?
C21A C26A 1.3755(19) . ?
C21A C22A 1.387(2) . ?
C22A C23A 1.376(2) . ?
C22A H22A 0.9400 . ?
C23A C24A 1.390(2) . ?
C23A H23A 0.9400 . ?
C24A C25A 1.387(2) . ?
C25A C26A 1.386(2) . ?
C25A H25A 0.9400 . ?
C26A H26A 0.9400 . ?
C27A H27A 0.9700 . ?
C27A H27B 0.9700 . ?
C27A H27C 0.9700 . ?
N1B C2B 1.2883(16) . ?
N1B C10B 1.3959(17) . ?
N3B C2B 1.3894(16) . ?
N3B C4B 1.4108(16) . ?
N3B C21B 1.4457(16) . ?
N4B C4B 1.2764(17) . ?
N4B H01B 0.91(2) . ?
O1B C24B 1.3645(15) . ?
O1B C27B 1.4276(18) . ?
C2B C11B 1.4902(18) . ?
C4B C5B 1.4613(18) . ?
C5B C10B 1.3962(19) . ?
C5B C6B 1.3981(19) . ?
C6B C7B 1.369(2) . ?
C6B H6B 0.9400 . ?
C7B C8B 1.392(2) . ?
C7B H7B 0.9400 . ?
C8B C9B 1.372(2) . ?
C8B H8B 0.9400 . ?
C9B C10B 1.4012(19) . ?
C9B H9B 0.9400 . ?
C11B C12B 1.3787(19) . ?
C11B C16B 1.3822(19) . ?
C12B C13B 1.381(2) . ?
C12B H12B 0.9400 . ?
C13B C14B 1.368(2) . ?
C13B H13B 0.9400 . ?
C14B C15B 1.374(2) . ?
C14B H14B 0.9400 . ?
C15B C16B 1.382(2) . ?
C15B H15B 0.9400 . ?
C16B H16B 0.9400 . ?
C21B C22B 1.3797(18) . ?
C21B C26B 1.3858(18) . ?
C22B C23B 1.3876(18) . ?
C22B H22B 0.9400 . ?
C23B C24B 1.3914(18) . ?
C23B H23B 0.9400 . ?
C24B C25B 1.3919(19) . ?
C25B C26B 1.3776(19) . ?
C25B H25B 0.9400 . ?
C26B H26B 0.9400 . ?
C27B H27D 0.9700 . ?
C27B H27E 0.9700 . ?
C27B H27F 0.9700 . ?
N1C C2C 1.2892(16) . ?
N1C C10C 1.3961(17) . ?
N3C C2C 1.3910(16) . ?
N3C C4C 1.4123(16) . ?
N3C C21C 1.4483(16) . ?
N4C C4C 1.2789(17) . ?
N4C H01C 0.949(19) . ?
O1C C24C 1.3698(16) . ?
O1C C27C 1.418(2) . ?
C2C C11C 1.4922(18) . ?
C4C C5C 1.4644(18) . ?
C5C C6C 1.3967(19) . ?
C5C C10C 1.3987(18) . ?
C6C C7C 1.369(2) . ?
C6C H6C 0.9400 . ?
C7C C8C 1.388(2) . ?
C7C H7C 0.9400 . ?
C8C C9C 1.375(2) . ?
C8C H8C 0.9400 . ?
C9C C10C 1.3989(18) . ?
C9C H9C 0.9400 . ?
C11C C12C 1.385(2) . ?
C11C C16C 1.3870(19) . ?
C12C C13C 1.383(2) . ?
C12C H12C 0.9400 . ?
C13C C14C 1.375(3) . ?
C13C H13C 0.9400 . ?
C14C C15C 1.368(3) . ?
C14C H14C 0.9400 . ?
C15C C16C 1.386(2) . ?
C15C H15C 0.9400 . ?
C16C H16C 0.9400 . ?
C21C C22C 1.3778(19) . ?
C21C C26C 1.3847(19) . ?
C22C C23C 1.3869(19) . ?
C22C H22C 0.9400 . ?
C23C C24C 1.3857(19) . ?
C23C H23C 0.9400 . ?
C24C C25C 1.386(2) . ?
C25C C26C 1.3793(19) . ?
C25C H25C 0.9400 . ?
C26C H26C 0.9400 . ?
C27C H27M 0.9700 . ?
C27C H27N 0.9700 . ?
C27C H27O 0.9700 . ?

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
C2A N1A C10A 117.94(11) . . ?
C2A N3A C4A 121.41(11) . . ?
C2A N3A C21A 121.72(11) . . ?
C4A N3A C21A 116.29(11) . . ?
C4A N4A H01A 110.9(15) . . ?
C24A O1A C27A 117.10(14) . . ?
N1A C2A N3A 124.42(12) . . ?
N1A C2A C11A 117.14(12) . . ?
N3A C2A C11A 118.44(11) . . ?
N4A C4A N3A 124.73(14) . . ?
N4A C4A C5A 120.90(14) . . ?
N3A C4A C5A 114.36(12) . . ?
C10A C5A C6A 119.83(13) . . ?
C10A C5A C4A 119.52(12) . . ?
C6A C5A C4A 120.64(13) . . ?
C7A C6A C5A 120.26(14) . . ?
C7A C6A H6A 119.9 . . ?
C5A C6A H6A 119.9 . . ?
C6A C7A C8A 120.07(14) . . ?
C6A C7A H7A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
C9A C8A C7A 120.52(14) . . ?
C9A C8A H8A 119.7 . . ?
C7A C8A H8A 119.7 . . ?
C8A C9A C10A 120.03(14) . . ?
C8A C9A H9A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C5A C10A N1A 122.31(12) . . ?
C5A C10A C9A 119.26(12) . . ?
N1A C10A C9A 118.42(12) . . ?
C12A C11A C16A 119.46(13) . . ?
C12A C11A C2A 118.03(12) . . ?
C16A C11A C2A 122.45(12) . . ?
C13A C12A C11A 120.11(15) . . ?
C13A C12A H12A 119.9 . . ?
C11A C12A H12A 119.9 . . ?
C14A C13A C12A 120.30(16) . . ?
C14A C13A H13A 119.8 . . ?
C12A C13A H13A 119.8 . . ?
C13A C14A C15A 120.01(15) . . ?
C13A C14A H14A 120.0 . . ?
C15A C14A H14A 120.0 . . ?
C14A C15A C16A 120.19(16) . . ?
C14A C15A H15A 119.9 . . ?
C16A C15A H15A 119.9 . . ?
C15A C16A C11A 119.92(16) . . ?
C15A C16A H16A 120.0 . . ?
C11A C16A H16A 120.0 . . ?
C26A C21A C22A 120.05(13) . . ?
C26A C21A N3A 120.00(12) . . ?
C22A C21A N3A 119.82(12) . . ?
C23A C22A C21A 119.64(14) . . ?
C23A C22A H22A 120.2 . . ?
C21A C22A H22A 120.2 . . ?
C22A C23A C24A 120.49(14) . . ?
C22A C23A H23A 119.8 . . ?
C24A C23A H23A 119.8 . . ?
O1A C24A C25A 124.68(14) . . ?
O1A C24A C23A 115.51(14) . . ?
C25A C24A C23A 119.80(13) . . ?
C26A C25A C24A 119.27(13) . . ?
C26A C25A H25A 120.4 . . ?
C24A C25A H25A 120.4 . . ?
C21A C26A C25A 120.73(13) . . ?
C21A C26A H26A 119.6 . . ?
C25A C26A H26A 119.6 . . ?
O1A C27A H27A 109.5 . . ?
O1A C27A H27B 109.5 . . ?
H27A C27A H27B 109.5 . . ?
O1A C27A H27C 109.5 . . ?
H27A C27A H27C 109.5 . . ?
H27B C27A H27C 109.5 . . ?
C2B N1B C10B 117.94(11) . . ?
C2B N3B C4B 121.67(10) . . ?
C2B N3B C21B 120.88(10) . . ?
C4B N3B C21B 117.04(10) . . ?
C4B N4B H01B 109.1(13) . . ?
C24B O1B C27B 117.80(11) . . ?
N1B C2B N3B 124.39(11) . . ?
N1B C2B C11B 117.75(11) . . ?
N3B C2B C11B 117.86(11) . . ?
N4B C4B N3B 124.13(12) . . ?
N4B C4B C5B 121.85(12) . . ?
N3B C4B C5B 114.01(11) . . ?
C10B C5B C6B 119.69(12) . . ?
C10B C5B C4B 119.65(11) . . ?
C6B C5B C4B 120.65(12) . . ?
C7B C6B C5B 120.16(14) . . ?
C7B C6B H6B 119.9 . . ?
C5B C6B H6B 119.9 . . ?
C6B C7B C8B 120.25(14) . . ?
C6B C7B H7B 119.9 . . ?
C8B C7B H7B 119.9 . . ?
C9B C8B C7B 120.49(14) . . ?
C9B C8B H8B 119.8 . . ?
C7B C8B H8B 119.8 . . ?
C8B C9B C10B 119.94(14) . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
N1B C10B C5B 122.06(11) . . ?
N1B C10B C9B 118.50(12) . . ?
C5B C10B C9B 119.44(12) . . ?
C12B C11B C16B 119.05(13) . . ?
C12B C11B C2B 119.33(12) . . ?
C16B C11B C2B 121.51(12) . . ?
C11B C12B C13B 120.63(14) . . ?
C11B C12B H12B 119.7 . . ?
C13B C12B H12B 119.7 . . ?
C14B C13B C12B 120.16(14) . . ?
C14B C13B H13B 119.9 . . ?
C12B C13B H13B 119.9 . . ?
C13B C14B C15B 119.63(14) . . ?
C13B C14B H14B 120.2 . . ?
C15B C14B H14B 120.2 . . ?
C14B C15B C16B 120.59(14) . . ?
C14B C15B H15B 119.7 . . ?
C16B C15B H15B 119.7 . . ?
C15B C16B C11B 119.93(14) . . ?
C15B C16B H16B 120.0 . . ?
C11B C16B H16B 120.0 . . ?
C22B C21B C26B 120.00(12) . . ?
C22B C21B N3B 120.28(11) . . ?
C26B C21B N3B 119.64(11) . . ?
C21B C22B C23B 120.63(12) . . ?
C21B C22B H22B 119.7 . . ?
C23B C22B H22B 119.7 . . ?
C22B C23B C24B 119.34(12) . . ?
C22B C23B H23B 120.3 . . ?
C24B C23B H23B 120.3 . . ?
O1B C24B C23B 124.31(12) . . ?
O1B C24B C25B 115.92(11) . . ?
C23B C24B C25B 119.76(12) . . ?
C26B C25B C24B 120.38(12) . . ?
C26B C25B H25B 119.8 . . ?
C24B C25B H25B 119.8 . . ?
C25B C26B C21B 119.89(12) . . ?
C25B C26B H26B 120.1 . . ?
C21B C26B H26B 120.1 . . ?
O1B C27B H27D 109.5 . . ?
O1B C27B H27E 109.5 . . ?
H27D C27B H27E 109.5 . . ?
O1B C27B H27F 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 109.5 . . ?
C2C N1C C10C 117.84(11) . . ?
C2C N3C C4C 121.90(10) . . ?
C2C N3C C21C 120.37(10) . . ?
C4C N3C C21C 117.58(10) . . ?
C4C N4C H01C 109.4(11) . . ?
C24C O1C C27C 117.45(11) . . ?
N1C C2C N3C 124.40(11) . . ?
N1C C2C C11C 118.09(11) . . ?
N3C C2C C11C 117.49(11) . . ?
N4C C4C N3C 124.77(12) . . ?
N4C C4C C5C 121.41(12) . . ?
N3C C4C C5C 113.82(10) . . ?
C6C C5C C10C 119.45(12) . . ?
C6C C5C C4C 120.88(12) . . ?
C10C C5C C4C 119.66(11) . . ?
C7C C6C C5C 120.57(13) . . ?
C7C C6C H6C 119.7 . . ?
C5C C6C H6C 119.7 . . ?
C6C C7C C8C 120.05(14) . . ?
C6C C7C H7C 120.0 . . ?
C8C C7C H7C 120.0 . . ?
C9C C8C C7C 120.42(13) . . ?
C9C C8C H8C 119.8 . . ?
C7C C8C H8C 119.8 . . ?
C8C C9C C10C 120.17(13) . . ?
C8C C9C H9C 119.9 . . ?
C10C C9C H9C 119.9 . . ?
N1C C10C C5C 122.22(11) . . ?
N1C C10C C9C 118.46(12) . . ?
C5C C10C C9C 119.31(12) . . ?
C12C C11C C16C 119.15(13) . . ?
C12C C11C C2C 118.69(12) . . ?
C16C C11C C2C 122.13(12) . . ?
C13C C12C C11C 120.05(15) . . ?
C13C C12C H12C 120.0 . . ?
C11C C12C H12C 120.0 . . ?
C14C C13C C12C 120.49(16) . . ?
C14C C13C H13C 119.8 . . ?
C12C C13C H13C 119.8 . . ?
C15C C14C C13C 119.81(15) . . ?
C15C C14C H14C 120.1 . . ?
C13C C14C H14C 120.1 . . ?
C14C C15C C16C 120.39(16) . . ?
C14C C15C H15C 119.8 . . ?
C16C C15C H15C 119.8 . . ?
C15C C16C C11C 120.09(15) . . ?
C15C C16C H16C 120.0 . . ?
C11C C16C H16C 120.0 . . ?
C22C C21C C26C 119.97(12) . . ?
C22C C21C N3C 119.92(11) . . ?
C26C C21C N3C 120.10(12) . . ?
C21C C22C C23C 120.55(12) . . ?
C21C C22C H22C 119.7 . . ?
C23C C22C H22C 119.7 . . ?
C24C C23C C22C 119.24(13) . . ?
C24C C23C H23C 120.4 . . ?
C22C C23C H23C 120.4 . . ?
O1C C24C C23C 124.08(13) . . ?
O1C C24C C25C 115.69(12) . . ?
C23C C24C C25C 120.22(12) . . ?
C26C C25C C24C 120.06(13) . . ?
C26C C25C H25C 120.0 . . ?
C24C C25C H25C 120.0 . . ?
C25C C26C C21C 119.91(13) . . ?
C25C C26C H26C 120.0 . . ?
C21C C26C H26C 120.0 . . ?
O1C C27C H27M 109.5 . . ?
O1C C27C H27N 109.5 . . ?
H27M C27C H27N 109.5 . . ?
O1C C27C H27O 109.5 . . ?
H27M C27C H27O 109.5 . . ?
H27N C27C H27O 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
C10A N1A C2A N3A -0.68(19) . . . . ?
C10A N1A C2A C11A 178.55(11) . . . . ?
C4A N3A C2A N1A 2.3(2) . . . . ?
C21A N3A C2A N1A 173.25(12) . . . . ?
C4A N3A C2A C11A -176.93(12) . . . . ?
C21A N3A C2A C11A -5.97(18) . . . . ?
C2A N3A C4A N4A 176.72(16) . . . . ?
C21A N3A C4A N4A 5.3(2) . . . . ?
C2A N3A C4A C5A -2.15(19) . . . . ?
C21A N3A C4A C5A -173.57(12) . . . . ?
N4A C4A C5A C10A -178.22(16) . . . . ?
N3A C4A C5A C10A 0.69(19) . . . . ?
N4A C4A C5A C6A 0.6(2) . . . . ?
N3A C4A C5A C6A 179.52(12) . . . . ?
C10A C5A C6A C7A -0.8(2) . . . . ?
C4A C5A C6A C7A -179.66(14) . . . . ?
C5A C6A C7A C8A -0.8(2) . . . . ?
C6A C7A C8A C9A 1.4(2) . . . . ?
C7A C8A C9A C10A -0.3(2) . . . . ?
C6A C5A C10A N1A -178.04(12) . . . . ?
C4A C5A C10A N1A 0.81(19) . . . . ?
C6A C5A C10A C9A 1.86(19) . . . . ?
C4A C5A C10A C9A -179.30(12) . . . . ?
C2A N1A C10A C5A -0.87(18) . . . . ?
C2A N1A C10A C9A 179.24(12) . . . . ?
C8A C9A C10A C5A -1.27(19) . . . . ?
C8A C9A C10A N1A 178.62(12) . . . . ?
N1A C2A C11A C12A -52.81(17) . . . . ?
N3A C2A C11A C12A 126.47(14) . . . . ?
N1A C2A C11A C16A 124.21(15) . . . . ?
N3A C2A C11A C16A -56.52(18) . . . . ?
C16A C11A C12A C13A 0.9(2) . . . . ?
C2A C11A C12A C13A 177.98(13) . . . . ?
C11A C12A C13A C14A -0.4(2) . . . . ?
C12A C13A C14A C15A -0.6(3) . . . . ?
C13A C14A C15A C16A 1.1(3) . . . . ?
C14A C15A C16A C11A -0.6(3) . . . . ?
C12A C11A C16A C15A -0.4(2) . . . . ?
C2A C11A C16A C15A -177.37(15) . . . . ?
C2A N3A C21A C26A -75.64(17) . . . . ?
C4A N3A C21A C26A 95.75(15) . . . . ?
C2A N3A C21A C22A 108.44(15) . . . . ?
C4A N3A C21A C22A -80.17(17) . . . . ?
C26A C21A C22A C23A -0.2(2) . . . . ?
N3A C21A C22A C23A 175.70(14) . . . . ?
C21A C22A C23A C24A -0.4(2) . . . . ?
C27A O1A C24A C25A -0.2(2) . . . . ?
C27A O1A C24A C23A -179.16(16) . . . . ?
C22A C23A C24A O1A -179.97(14) . . . . ?
C22A C23A C24A C25A 1.0(2) . . . . ?
O1A C24A C25A C26A -179.87(14) . . . . ?
C23A C24A C25A C26A -0.9(2) . . . . ?
C22A C21A C26A C25A 0.3(2) . . . . ?
N3A C21A C26A C25A -175.63(12) . . . . ?
C24A C25A C26A C21A 0.3(2) . . . . ?
C10B N1B C2B N3B 2.76(19) . . . . ?
C10B N1B C2B C11B -177.16(11) . . . . ?
C4B N3B C2B N1B 1.53(19) . . . . ?
C21B N3B C2B N1B 173.99(12) . . . . ?
C4B N3B C2B C11B -178.54(11) . . . . ?
C21B N3B C2B C11B -6.09(16) . . . . ?
C2B N3B C4B N4B 174.23(13) . . . . ?
C21B N3B C4B N4B 1.50(18) . . . . ?
C2B N3B C4B C5B -5.25(16) . . . . ?
C21B N3B C4B C5B -177.98(10) . . . . ?
N4B C4B C5B C10B -174.57(13) . . . . ?
N3B C4B C5B C10B 4.92(17) . . . . ?
N4B C4B C5B C6B 4.1(2) . . . . ?
N3B C4B C5B C6B -176.40(12) . . . . ?
C10B C5B C6B C7B -1.5(2) . . . . ?
C4B C5B C6B C7B 179.86(13) . . . . ?
C5B C6B C7B C8B 1.4(2) . . . . ?
C6B C7B C8B C9B -0.4(3) . . . . ?
C7B C8B C9B C10B -0.5(2) . . . . ?
C2B N1B C10B C5B -2.92(19) . . . . ?
C2B N1B C10B C9B 176.78(12) . . . . ?
C6B C5B C10B N1B -179.77(12) . . . . ?
C4B C5B C10B N1B -1.08(19) . . . . ?
C6B C5B C10B C9B 0.54(19) . . . . ?
C4B C5B C10B C9B 179.23(12) . . . . ?
C8B C9B C10B N1B -179.25(13) . . . . ?
C8B C9B C10B C5B 0.4(2) . . . . ?
N1B C2B C11B C12B -67.86(16) . . . . ?
N3B C2B C11B C12B 112.21(14) . . . . ?
N1B C2B C11B C16B 108.25(15) . . . . ?
N3B C2B C11B C16B -71.67(16) . . . . ?
C16B C11B C12B C13B 0.8(2) . . . . ?
C2B C11B C12B C13B 177.01(13) . . . . ?
C11B C12B C13B C14B -0.3(2) . . . . ?
C12B C13B C14B C15B -0.5(2) . . . . ?
C13B C14B C15B C16B 0.9(2) . . . . ?
C14B C15B C16B C11B -0.4(3) . . . . ?
C12B C11B C16B C15B -0.4(2) . . . . ?
C2B C11B C16B C15B -176.54(14) . . . . ?
C2B N3B C21B C22B 104.30(14) . . . . ?
C4B N3B C21B C22B -82.90(15) . . . . ?
C2B N3B C21B C26B -79.19(15) . . . . ?
C4B N3B C21B C26B 93.60(14) . . . . ?
C26B C21B C22B C23B 0.35(19) . . . . ?
N3B C21B C22B C23B 176.85(11) . . . . ?
C21B C22B C23B C24B -0.15(19) . . . . ?
C27B O1B C24B C23B 1.63(18) . . . . ?
C27B O1B C24B C25B -177.74(12) . . . . ?
C22B C23B C24B O1B -178.93(12) . . . . ?
C22B C23B C24B C25B 0.42(19) . . . . ?
O1B C24B C25B C26B 178.48(12) . . . . ?
C23B C24B C25B C26B -0.9(2) . . . . ?
C24B C25B C26B C21B 1.1(2) . . . . ?
C22B C21B C26B C25B -0.84(19) . . . . ?
N3B C21B C26B C25B -177.36(12) . . . . ?
C10C N1C C2C N3C -1.39(19) . . . . ?
C10C N1C C2C C11C -179.83(11) . . . . ?
C4C N3C C2C N1C -2.38(19) . . . . ?
C21C N3C C2C N1C -177.85(12) . . . . ?
C4C N3C C2C C11C 176.07(11) . . . . ?
C21C N3C C2C C11C 0.60(17) . . . . ?
C2C N3C C4C N4C -175.57(13) . . . . ?
C21C N3C C4C N4C 0.0(2) . . . . ?
C2C N3C C4C C5C 4.25(17) . . . . ?
C21C N3C C4C C5C 179.84(10) . . . . ?
N4C C4C C5C C6C -2.9(2) . . . . ?
N3C C4C C5C C6C 177.32(12) . . . . ?
N4C C4C C5C C10C 177.12(13) . . . . ?
N3C C4C C5C C10C -2.71(17) . . . . ?
C10C C5C C6C C7C 1.7(2) . . . . ?
C4C C5C C6C C7C -178.35(13) . . . . ?
C5C C6C C7C C8C -1.2(2) . . . . ?
C6C C7C C8C C9C -0.3(2) . . . . ?
C7C C8C C9C C10C 1.3(2) . . . . ?
C2C N1C C10C C5C 2.91(18) . . . . ?
C2C N1C C10C C9C -177.18(12) . . . . ?
C6C C5C C10C N1C 179.23(12) . . . . ?
C4C C5C C10C N1C -0.75(19) . . . . ?
C6C C5C C10C C9C -0.68(19) . . . . ?
C4C C5C C10C C9C 179.34(12) . . . . ?
C8C C9C C10C N1C 179.32(12) . . . . ?
C8C C9C C10C C5C -0.8(2) . . . . ?
N1C C2C C11C C12C 58.03(17) . . . . ?
N3C C2C C11C C12C -120.52(14) . . . . ?
N1C C2C C11C C16C -119.82(14) . . . . ?
N3C C2C C11C C16C 61.63(17) . . . . ?
C16C C11C C12C C13C -1.7(2) . . . . ?
C2C C11C C12C C13C -179.66(14) . . . . ?
C11C C12C C13C C14C 0.7(3) . . . . ?
C12C C13C C14C C15C 0.5(3) . . . . ?
C13C C14C C15C C16C -0.6(3) . . . . ?
C14C C15C C16C C11C -0.5(2) . . . . ?
C12C C11C C16C C15C 1.7(2) . . . . ?
C2C C11C C16C C15C 179.49(12) . . . . ?
C2C N3C C21C C22C -102.83(14) . . . . ?
C4C N3C C21C C22C 81.51(15) . . . . ?
C2C N3C C21C C26C 76.42(15) . . . . ?
C4C N3C C21C C26C -99.24(14) . . . . ?
C26C C21C C22C C23C -2.14(19) . . . . ?
N3C C21C C22C C23C 177.11(12) . . . . ?
C21C C22C C23C C24C 0.3(2) . . . . ?
C27C O1C C24C C23C 16.0(2) . . . . ?
C27C O1C C24C C25C -164.02(13) . . . . ?
C22C C23C C24C O1C -178.86(12) . . . . ?
C22C C23C C24C C25C 1.2(2) . . . . ?
O1C C24C C25C C26C 179.23(12) . . . . ?
C23C C24C C25C C26C -0.8(2) . . . . ?
C24C C25C C26C C21C -1.1(2) . . . . ?
C22C C21C C26C C25C 2.5(2) . . . . ?
N3C C21C C26C C25C -176.74(12) . . . . ?

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
C13C H13C O1B 0.94 2.85 3.668(2) 146.6 1_554
C23B H23B N4B 0.94 2.78 3.4534(18) 129.6 2_676
C27A H27B N4A 0.97 2.93 3.743(2) 141.7 2_767
C13B H13B N4A 0.94 2.67 3.375(2) 132.7 2_766
C9A H9A N1A 0.94 2.70 3.6322(18) 171.4 2_666
C16B H16B O1C 0.94 2.71 3.5338(18) 147.1 2_775
C25C H25C N1B 0.94 2.72 3.3277(17) 123.2 2_775
C14A H14A O1A 0.94 2.90 3.601(2) 132.4 2_667

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        67.52
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.029
####################################################################### 
# 
# 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_5cd
_database_code_depnum_ccdc_archive 'CCDC 1008259'
_audit_update_record             
;
2014-06-13 deposited with the CCDC.
2015-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Cl N3'
_chemical_formula_weight         333.81

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   14.6582(9)
_cell_length_b                   17.3558(12)
_cell_length_c                   7.0639(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.146(3)
_cell_angle_gamma                90.00
_cell_volume                     1779.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      4.694
_cell_measurement_theta_max      51.005

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14711
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3634
_reflns_number_gt                2634
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
 
 The hydrogens at N4 atom were refined freely, but with N-H distance 
 restraints (SADI).

 A badly disordered methanol molecule over tree positions was found in the
 asymmetrical unit and could not be satisfactorily refined. The program 
 SQUEEZE (A. L. Spek J. Appl. Cryst., 2003, 36, 7-13) was therefore used to
 remove mathematically the effect of the solvent. 
 The quoted formula and derived parameters are not included the squeezed
 solvent molecule. 
;

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.270 0.250 -0.033 72 25 ' '
2 0.730 0.750 -0.003 72 25 ' '

_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)+(0.0621P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3634
_refine_ls_number_parameters     225
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_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
Cl1 Cl 0.36913(3) 0.05943(2) 0.35957(7) 0.06172(18) Uani 1 1 d . . .
N1 N 0.74570(8) 0.25735(7) 0.20260(17) 0.0372(3) Uani 1 1 d . . .
C2 C 0.77271(10) 0.18652(8) 0.2076(2) 0.0353(3) Uani 1 1 d . . .
N3 N 0.71859(8) 0.12513(7) 0.25544(16) 0.0362(3) Uani 1 1 d . . .
N4 N 0.58003(10) 0.07744(8) 0.3268(2) 0.0447(3) Uani 1 1 d D . .
H01 H 0.5212(11) 0.0845(10) 0.339(3) 0.064(6) Uiso 1 1 d D . .
H02 H 0.6084(14) 0.0318(10) 0.373(3) 0.080(6) Uiso 1 1 d D . .
C4 C 0.62895(10) 0.13614(8) 0.28350(19) 0.0347(3) Uani 1 1 d . . .
C5 C 0.59493(10) 0.21394(8) 0.2720(2) 0.0356(3) Uani 1 1 d . . .
C6 C 0.50568(10) 0.23327(9) 0.3033(2) 0.0430(4) Uani 1 1 d . . .
H6 H 0.4637 0.1947 0.3208 0.052 Uiso 1 1 calc R . .
C7 C 0.48018(11) 0.30881(9) 0.3081(2) 0.0496(4) Uani 1 1 d . . .
H7 H 0.4205 0.3214 0.3270 0.060 Uiso 1 1 calc R . .
C8 C 0.54256(11) 0.36699(10) 0.2849(2) 0.0480(4) Uani 1 1 d . . .
H8 H 0.5249 0.4182 0.2921 0.058 Uiso 1 1 calc R . .
C9 C 0.63003(11) 0.34954(8) 0.2515(2) 0.0410(4) Uani 1 1 d . . .
H9 H 0.6711 0.3889 0.2345 0.049 Uiso 1 1 calc R . .
C10 C 0.65759(10) 0.27255(8) 0.24307(19) 0.0357(3) Uani 1 1 d . . .
C11 C 0.86657(10) 0.16879(9) 0.1626(2) 0.0376(3) Uani 1 1 d . . .
C12 C 0.88279(12) 0.11497(9) 0.0249(2) 0.0476(4) Uani 1 1 d . . .
H12 H 0.8340 0.0874 -0.0413 0.057 Uiso 1 1 calc R . .
C13 C 0.97133(13) 0.10266(10) -0.0130(3) 0.0567(5) Uani 1 1 d . . .
H13 H 0.9821 0.0670 -0.1055 0.068 Uiso 1 1 calc R . .
C14 C 1.04405(12) 0.14299(11) 0.0859(3) 0.0591(5) Uani 1 1 d . . .
H14 H 1.1038 0.1338 0.0614 0.071 Uiso 1 1 calc R . .
C15 C 1.02847(12) 0.19670(10) 0.2201(3) 0.0562(5) Uani 1 1 d . . .
H15 H 1.0776 0.2242 0.2856 0.067 Uiso 1 1 calc R . .
C16 C 0.94021(11) 0.21004(9) 0.2583(2) 0.0470(4) Uani 1 1 d . . .
H16 H 0.9299 0.2469 0.3486 0.056 Uiso 1 1 calc R . .
C21 C 0.76058(10) 0.04963(8) 0.2938(2) 0.0409(4) Uani 1 1 d . . .
C22 C 0.73549(12) -0.01074(10) 0.1700(3) 0.0536(4) Uani 1 1 d . . .
H22 H 0.6910 -0.0044 0.0635 0.064 Uiso 1 1 calc R . .
C23 C 0.77877(16) -0.08098(11) 0.2094(4) 0.0724(6) Uani 1 1 d . . .
H23 H 0.7627 -0.1228 0.1295 0.087 Uiso 1 1 calc R . .
C24 C 0.84530(18) -0.08935(13) 0.3657(4) 0.0876(8) Uani 1 1 d . . .
H24 H 0.8748 -0.1365 0.3892 0.105 Uiso 1 1 calc R . .
C25 C 0.86839(15) -0.02924(14) 0.4863(3) 0.0790(7) Uani 1 1 d . . .
H25 H 0.9134 -0.0357 0.5919 0.095 Uiso 1 1 calc R . .
C26 C 0.82547(12) 0.04147(10) 0.4531(3) 0.0549(5) Uani 1 1 d . . .
H26 H 0.8402 0.0825 0.5366 0.066 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
N1 C2 1.2905(18) . ?
N1 C10 1.3872(18) . ?
C2 N3 1.3982(18) . ?
C2 C11 1.487(2) . ?
N3 C4 1.3697(18) . ?
N3 C21 1.4567(18) . ?
N4 C4 1.3069(19) . ?
N4 H01 0.887(16) . ?
N4 H02 0.932(16) . ?
C4 C5 1.438(2) . ?
C5 C6 1.398(2) . ?
C5 C10 1.405(2) . ?
C6 C7 1.365(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.370(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.400(2) . ?
C9 H9 0.9300 . ?
C11 C16 1.388(2) . ?
C11 C12 1.393(2) . ?
C12 C13 1.378(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C26 1.374(2) . ?
C21 C22 1.381(2) . ?
C22 C23 1.384(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.373(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.359(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.384(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C10 117.81(12) . . ?
N1 C2 N3 123.38(13) . . ?
N1 C2 C11 118.73(13) . . ?
N3 C2 C11 117.89(12) . . ?
C4 N3 C2 121.16(12) . . ?
C4 N3 C21 119.16(11) . . ?
C2 N3 C21 119.42(11) . . ?
C4 N4 H01 119.1(12) . . ?
C4 N4 H02 120.8(13) . . ?
H01 N4 H02 118.4(17) . . ?
N4 C4 N3 119.63(13) . . ?
N4 C4 C5 123.23(14) . . ?
N3 C4 C5 117.07(12) . . ?
C6 C5 C10 119.66(13) . . ?
C6 C5 C4 122.77(13) . . ?
C10 C5 C4 117.36(13) . . ?
C7 C6 C5 120.01(14) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.58(15) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 120.52(15) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.08(14) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
N1 C10 C9 118.24(13) . . ?
N1 C10 C5 122.64(13) . . ?
C9 C10 C5 119.11(13) . . ?
C16 C11 C12 119.20(14) . . ?
C16 C11 C2 117.91(13) . . ?
C12 C11 C2 122.85(14) . . ?
C13 C12 C11 119.87(16) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.30(17) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.15(16) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.15(17) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.31(16) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C26 C21 C22 122.13(15) . . ?
C26 C21 N3 118.06(14) . . ?
C22 C21 N3 119.80(15) . . ?
C21 C22 C23 117.86(19) . . ?
C21 C22 H22 121.1 . . ?
C23 C22 H22 121.1 . . ?
C24 C23 C22 120.5(2) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 120.5(2) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 120.5(2) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 118.39(19) . . ?
C21 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C2 N3 -1.4(2) . . . . ?
C10 N1 C2 C11 179.34(12) . . . . ?
N1 C2 N3 C4 6.1(2) . . . . ?
C11 C2 N3 C4 -174.68(12) . . . . ?
N1 C2 N3 C21 -168.05(13) . . . . ?
C11 C2 N3 C21 11.18(19) . . . . ?
C2 N3 C4 N4 179.53(13) . . . . ?
C21 N3 C4 N4 -6.3(2) . . . . ?
C2 N3 C4 C5 -3.37(19) . . . . ?
C21 N3 C4 C5 170.79(12) . . . . ?
N4 C4 C5 C6 -1.1(2) . . . . ?
N3 C4 C5 C6 -178.11(13) . . . . ?
N4 C4 C5 C10 173.75(14) . . . . ?
N3 C4 C5 C10 -3.24(19) . . . . ?
C10 C5 C6 C7 -0.9(2) . . . . ?
C4 C5 C6 C7 173.87(14) . . . . ?
C5 C6 C7 C8 -0.9(2) . . . . ?
C6 C7 C8 C9 1.8(3) . . . . ?
C7 C8 C9 C10 -0.9(2) . . . . ?
C2 N1 C10 C9 175.50(13) . . . . ?
C2 N1 C10 C5 -5.7(2) . . . . ?
C8 C9 C10 N1 177.87(13) . . . . ?
C8 C9 C10 C5 -0.9(2) . . . . ?
C6 C5 C10 N1 -176.95(12) . . . . ?
C4 C5 C10 N1 8.0(2) . . . . ?
C6 C5 C10 C9 1.8(2) . . . . ?
C4 C5 C10 C9 -173.22(13) . . . . ?
N1 C2 C11 C16 50.90(19) . . . . ?
N3 C2 C11 C16 -128.37(15) . . . . ?
N1 C2 C11 C12 -126.78(16) . . . . ?
N3 C2 C11 C12 53.95(19) . . . . ?
C16 C11 C12 C13 0.8(2) . . . . ?
C2 C11 C12 C13 178.43(14) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C14 C15 C16 C11 0.6(3) . . . . ?
C12 C11 C16 C15 -1.3(2) . . . . ?
C2 C11 C16 C15 -179.09(14) . . . . ?
C4 N3 C21 C26 -107.65(16) . . . . ?
C2 N3 C21 C26 66.60(18) . . . . ?
C4 N3 C21 C22 73.18(18) . . . . ?
C2 N3 C21 C22 -112.57(16) . . . . ?
C26 C21 C22 C23 -0.7(2) . . . . ?
N3 C21 C22 C23 178.45(14) . . . . ?
C21 C22 C23 C24 -0.9(3) . . . . ?
C22 C23 C24 C25 1.3(3) . . . . ?
C23 C24 C25 C26 -0.2(3) . . . . ?
C22 C21 C26 C25 1.8(2) . . . . ?
N3 C21 C26 C25 -177.40(16) . . . . ?
C24 C25 C26 C21 -1.3(3) . . . . ?

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
N4 H01 Cl1 0.887(16) 2.296(17) 3.1483(15) 161.0(16) .
N4 H02 Cl1 0.932(16) 2.450(18) 3.2616(15) 145.6(17) 3_656

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.039
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_erk7548
_database_code_depnum_ccdc_archive 'CCDC 1008260'
_audit_update_record             
;
2014-06-13 deposited with the CCDC.
2015-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 N3 O'
_chemical_formula_weight         265.31

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   8.9276(2)
_cell_length_b                   9.0785(2)
_cell_length_c                   16.8687(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.058(2)
_cell_angle_gamma                90.00
_cell_volume                     1359.56(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2733
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9753
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8031
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.17
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2695
_reflns_number_gt                2386
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The hydrogens at O1 atom were refined freely.
;

_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)+(0.0382P)²+0.5074P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2695
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
N1 N 0.49623(13) 0.55700(13) 0.15125(7) 0.0385(3) Uani 1 1 d . . .
N3 N 0.28864(12) 0.41144(13) 0.10479(7) 0.0382(3) Uani 1 1 d . . .
N4 N 0.04342(13) 0.47928(15) 0.10140(8) 0.0458(3) Uani 1 1 d . . .
O1 O 0.78538(15) 0.66508(15) 0.11227(9) 0.0638(4) Uani 1 1 d . . .
H01 H 0.705(3) 0.617(2) 0.1281(14) 0.085(7) Uiso 1 1 d . . .
H02 H 0.861(3) 0.595(3) 0.1114(14) 0.093(8) Uiso 1 1 d . . .
C2 C 0.43894(15) 0.43250(15) 0.12408(8) 0.0361(3) Uani 1 1 d . . .
C11 C 0.54103(15) 0.30547(15) 0.11451(9) 0.0381(3) Uani 1 1 d . . .
C12 C 0.54739(17) 0.23947(18) 0.04081(9) 0.0462(4) Uani 1 1 d . . .
H12 H 0.4873 0.2753 -0.0042 0.055 Uiso 1 1 calc R . .
C13 C 0.64233(19) 0.12066(19) 0.03342(10) 0.0511(4) Uani 1 1 d . . .
H13 H 0.6483 0.0778 -0.0169 0.061 Uiso 1 1 calc R . .
C14 C 0.72817(17) 0.06485(18) 0.09945(11) 0.0493(4) Uani 1 1 d . . .
H14 H 0.7899 -0.0178 0.0944 0.059 Uiso 1 1 calc R . .
C15 C 0.72306(17) 0.13086(17) 0.17305(10) 0.0473(4) Uani 1 1 d . . .
H15 H 0.7821 0.0935 0.2180 0.057 Uiso 1 1 calc R . .
C16 C 0.63105(16) 0.25205(17) 0.18065(9) 0.0423(3) Uani 1 1 d . . .
H16 H 0.6295 0.2981 0.2305 0.051 Uiso 1 1 calc R . .
C10 C 0.39698(15) 0.67384(15) 0.16053(8) 0.0365(3) Uani 1 1 d . . .
C9 C 0.45746(17) 0.80900(16) 0.18840(9) 0.0425(3) Uani 1 1 d . . .
H9 H 0.5623 0.8196 0.1996 0.051 Uiso 1 1 calc R . .
C8 C 0.36424(18) 0.92617(17) 0.19941(9) 0.0458(4) Uani 1 1 d . . .
H8 H 0.4059 1.0166 0.2177 0.055 Uiso 1 1 calc R . .
C7 C 0.20854(18) 0.91188(17) 0.18372(10) 0.0470(4) Uani 1 1 d . . .
H7 H 0.1457 0.9921 0.1923 0.056 Uiso 1 1 calc R . .
C6 C 0.14653(17) 0.78092(17) 0.15570(9) 0.0436(3) Uani 1 1 d . . .
H6 H 0.0415 0.7717 0.1449 0.052 Uiso 1 1 calc R . .
C5 C 0.23993(15) 0.66142(16) 0.14336(8) 0.0372(3) Uani 1 1 d . . .
C4 C 0.18086(15) 0.51963(16) 0.11528(8) 0.0376(3) Uani 1 1 d . . .
C21 C 0.04354(17) 0.32223(18) 0.07894(11) 0.0516(4) Uani 1 1 d . . .
H21A H -0.0089 0.3085 0.0254 0.062 Uiso 1 1 calc R . .
H21B H -0.0078 0.2635 0.1166 0.062 Uiso 1 1 calc R . .
C22 C 0.20821(18) 0.27416(17) 0.08071(11) 0.0524(4) Uani 1 1 d . . .
H22A H 0.2325 0.1954 0.1197 0.063 Uiso 1 1 calc R . .
H22B H 0.2315 0.2410 0.0281 0.063 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
N1 C2 1.3037(18) . ?
N1 C10 1.4014(17) . ?
N3 C2 1.3604(17) . ?
N3 C4 1.3992(18) . ?
N3 C22 1.4739(18) . ?
N4 C4 1.2783(18) . ?
N4 C21 1.475(2) . ?
O1 H01 0.90(3) . ?
O1 H02 0.93(3) . ?
C2 C11 1.4892(19) . ?
C11 C12 1.387(2) . ?
C11 C16 1.392(2) . ?
C12 C13 1.385(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.380(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.384(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C10 C9 1.402(2) . ?
C10 C5 1.4060(19) . ?
C9 C8 1.375(2) . ?
C9 H9 0.9400 . ?
C8 C7 1.393(2) . ?
C8 H8 0.9400 . ?
C7 C6 1.374(2) . ?
C7 H7 0.9400 . ?
C6 C5 1.397(2) . ?
C6 H6 0.9400 . ?
C5 C4 1.452(2) . ?
C21 C22 1.531(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 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
C2 N1 C10 117.79(11) . . ?
C2 N3 C4 123.04(12) . . ?
C2 N3 C22 128.63(12) . . ?
C4 N3 C22 107.87(11) . . ?
C4 N4 C21 107.29(12) . . ?
H01 O1 H02 106(2) . . ?
N1 C2 N3 123.12(13) . . ?
N1 C2 C11 119.19(12) . . ?
N3 C2 C11 117.69(12) . . ?
C12 C11 C16 119.56(14) . . ?
C12 C11 C2 121.02(13) . . ?
C16 C11 C2 119.42(13) . . ?
C13 C12 C11 120.03(14) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.41(15) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.81(15) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.16(14) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 119.99(14) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
N1 C10 C9 118.32(12) . . ?
N1 C10 C5 123.01(13) . . ?
C9 C10 C5 118.67(13) . . ?
C8 C9 C10 120.35(13) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C8 C7 120.54(14) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C6 C7 C8 120.23(14) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C6 C5 119.86(14) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C5 C10 120.33(13) . . ?
C6 C5 C4 122.36(13) . . ?
C10 C5 C4 117.28(12) . . ?
N4 C4 N3 115.81(13) . . ?
N4 C4 C5 128.50(13) . . ?
N3 C4 C5 115.65(12) . . ?
N4 C21 C22 107.29(12) . . ?
N4 C21 H21A 110.3 . . ?
C22 C21 H21A 110.3 . . ?
N4 C21 H21B 110.3 . . ?
C22 C21 H21B 110.3 . . ?
H21A C21 H21B 108.5 . . ?
N3 C22 C21 101.73(12) . . ?
N3 C22 H22A 111.4 . . ?
C21 C22 H22A 111.4 . . ?
N3 C22 H22B 111.4 . . ?
C21 C22 H22B 111.4 . . ?
H22A C22 H22B 109.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C2 N3 -0.2(2) . . . . ?
C10 N1 C2 C11 -179.20(11) . . . . ?
C4 N3 C2 N1 -2.6(2) . . . . ?
C22 N3 C2 N1 -173.87(15) . . . . ?
C4 N3 C2 C11 176.43(12) . . . . ?
C22 N3 C2 C11 5.2(2) . . . . ?
N1 C2 C11 C12 -121.14(15) . . . . ?
N3 C2 C11 C12 59.78(18) . . . . ?
N1 C2 C11 C16 59.04(18) . . . . ?
N3 C2 C11 C16 -120.04(15) . . . . ?
C16 C11 C12 C13 0.3(2) . . . . ?
C2 C11 C12 C13 -179.49(14) . . . . ?
C11 C12 C13 C14 1.7(2) . . . . ?
C12 C13 C14 C15 -2.1(2) . . . . ?
C13 C14 C15 C16 0.5(2) . . . . ?
C14 C15 C16 C11 1.4(2) . . . . ?
C12 C11 C16 C15 -1.9(2) . . . . ?
C2 C11 C16 C15 177.95(13) . . . . ?
C2 N1 C10 C9 -178.92(12) . . . . ?
C2 N1 C10 C5 1.2(2) . . . . ?
N1 C10 C9 C8 -179.16(13) . . . . ?
C5 C10 C9 C8 0.7(2) . . . . ?
C10 C9 C8 C7 0.6(2) . . . . ?
C9 C8 C7 C6 -1.1(2) . . . . ?
C8 C7 C6 C5 0.4(2) . . . . ?
C7 C6 C5 C10 0.9(2) . . . . ?
C7 C6 C5 C4 178.85(13) . . . . ?
N1 C10 C5 C6 178.42(13) . . . . ?
C9 C10 C5 C6 -1.4(2) . . . . ?
N1 C10 C5 C4 0.4(2) . . . . ?
C9 C10 C5 C4 -179.48(12) . . . . ?
C21 N4 C4 N3 1.01(18) . . . . ?
C21 N4 C4 C5 -176.45(14) . . . . ?
C2 N3 C4 N4 -173.76(13) . . . . ?
C22 N3 C4 N4 -0.93(18) . . . . ?
C2 N3 C4 C5 4.03(19) . . . . ?
C22 N3 C4 C5 176.86(12) . . . . ?
C6 C5 C4 N4 -3.4(2) . . . . ?
C10 C5 C4 N4 174.63(14) . . . . ?
C6 C5 C4 N3 179.15(13) . . . . ?
C10 C5 C4 N3 -2.83(18) . . . . ?
C4 N4 C21 C22 -0.68(18) . . . . ?
C2 N3 C22 C21 172.69(14) . . . . ?
C4 N3 C22 C21 0.39(16) . . . . ?
N4 C21 C22 N3 0.14(17) . . . . ?

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
O1 H01 N1 0.90(3) 2.02(3) 2.9012(18) 165(2) .
O1 H02 N4 0.93(3) 1.96(3) 2.8766(19) 168(2) 1_655

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.030
#=============================================================================
#  end of cif data for "erk7548" (compound 9)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================
####################################################################### 
# 
# 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_dan7902
_database_code_depnum_ccdc_archive 'CCDC 1057208'
_audit_update_record             
;
2015-03-31 deposited with the CCDC.
2015-04-23 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 Cl N3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         411.87

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7886(2)
_cell_length_b                   9.9350(3)
_cell_length_c                   13.6151(4)
_cell_angle_alpha                83.463(2)
_cell_angle_beta                 84.947(2)
_cell_angle_gamma                73.188(2)
_cell_volume                     1000.26(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6019
_cell_measurement_theta_min      4.6697
_cell_measurement_theta_max      65.2262
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432

_exptl_absorpt_coefficient_mu    1.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'KappaCCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            16418
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_theta_min         4.67
_diffrn_reflns_theta_max         65.20
_diffrn_reflns_theta_full        65.20
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
 The hydrogens at N2 and O3 atoms were refined freely.

 One hydrogen from water molecule is disordered over two positions.
 The SADI restraint was used in order to improve refinement stability.
;

_reflns_number_total             3365
_reflns_number_gt                2859
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0910
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_number_reflns         3365
_refine_ls_number_parameters     285
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²+0.3760P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX2 v.2014.5-0 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 1.28696(6) 0.59842(5) 0.31019(3) 0.02280(14) Uani d . . . 1.0 . .
N N1 1.5688(2) 0.85610(16) 0.68102(11) 0.0197(3) Uani d . . . 1.0 . .
N N2 1.2918(2) 0.64396(17) 0.54030(13) 0.0220(4) Uani d . . . 1.0 . .
H H1 1.309(3) 0.637(2) 0.475(2) 0.033(6) Uiso d . . . 1.0 . .
H H2 1.203(4) 0.615(3) 0.576(2) 0.055(8) Uiso d . . . 1.0 . .
N N3 1.36035(19) 0.72256(15) 0.68157(11) 0.0163(3) Uani d . . . 1.0 . .
O O1 1.04132(17) 0.90852(12) 0.72548(9) 0.0200(3) Uani d . . . 1.0 . .
O O2 1.15669(17) 0.34124(13) 0.85202(10) 0.0224(3) Uani d . . . 1.0 . .
O O3 0.9829(2) 0.56098(17) 0.59056(12) 0.0281(3) Uani d . . D 1.0 . .
H H3 0.920(4) 0.515(3) 0.627(2) 0.039(7) Uiso d . . . 1.0 . .
H H4 1.003(8) 0.514(6) 0.536(3) 0.06(2) Uiso d . P D 0.55(6) A 1
H H4A 0.905(8) 0.649(5) 0.587(5) 0.06(3) Uiso d . P D 0.45(6) A 2
C C2 1.4545(2) 0.79686(18) 0.72728(13) 0.0173(4) Uani d . . . 1.0 . .
C C4 1.3895(2) 0.70619(18) 0.58271(13) 0.0181(4) Uani d . . . 1.0 . .
C C5 1.5812(3) 0.7393(2) 0.43007(14) 0.0223(4) Uani d . . . 1.0 . .
H H5 1.5259 0.6875 0.3947 0.027 Uiso calc U . R 1.0 . .
C C6 1.7134(3) 0.7940(2) 0.38381(15) 0.0264(5) Uani d . . . 1.0 . .
H H6 1.7512 0.7783 0.3168 0.032 Uiso calc U . R 1.0 . .
C C7 1.7931(3) 0.8730(2) 0.43490(15) 0.0277(5) Uani d . . . 1.0 . .
H H7 1.8836 0.9113 0.402 0.033 Uiso calc U . R 1.0 . .
C C8 1.7411(3) 0.8954(2) 0.53204(14) 0.0246(4) Uani d . . . 1.0 . .
H H8 1.7949 0.9498 0.5659 0.029 Uiso calc U . R 1.0 . .
C C9 1.6092(2) 0.83839(19) 0.58123(14) 0.0202(4) Uani d . . . 1.0 . .
C C10 1.5277(2) 0.76008(18) 0.52988(13) 0.0182(4) Uani d . . . 1.0 . .
C C11 1.4250(2) 0.80184(19) 0.83615(14) 0.0184(4) Uani d . . . 1.0 . .
C C12 1.4894(3) 0.6791(2) 0.89817(14) 0.0209(4) Uani d . . . 1.0 . .
H H12 1.5395 0.5913 0.8709 0.025 Uiso calc U . R 1.0 . .
C C13 1.4805(3) 0.6851(2) 0.99961(14) 0.0240(4) Uani d . . . 1.0 . .
H H13 1.5277 0.6016 1.0416 0.029 Uiso calc U . R 1.0 . .
C C14 1.4037(3) 0.8113(2) 1.04013(15) 0.0271(5) Uani d . . . 1.0 . .
H H14 1.3952 0.8145 1.1099 0.032 Uiso calc U . R 1.0 . .
C C15 1.3388(3) 0.9338(2) 0.97839(15) 0.0305(5) Uani d . . . 1.0 . .
H H15 1.2852 1.0209 1.0061 0.037 Uiso calc U . R 1.0 . .
C C16 1.3517(3) 0.9295(2) 0.87659(15) 0.0256(4) Uani d . . . 1.0 . .
H H16 1.3105 1.014 0.8345 0.031 Uiso calc U . R 1.0 . .
C C21 1.2213(2) 0.67236(19) 0.73907(13) 0.0168(4) Uani d . . . 1.0 . .
C C22 1.0583(2) 0.77103(18) 0.76207(13) 0.0172(4) Uani d . . . 1.0 . .
C C23 0.9276(2) 0.72385(19) 0.81943(13) 0.0190(4) Uani d . . . 1.0 . .
H H23 0.8168 0.7893 0.8375 0.023 Uiso calc U . R 1.0 . .
C C24 0.9579(2) 0.58106(19) 0.85071(13) 0.0192(4) Uani d . . . 1.0 . .
H H24 0.8673 0.5498 0.8899 0.023 Uiso calc U . R 1.0 . .
C C25 1.1187(2) 0.48393(18) 0.82529(13) 0.0183(4) Uani d . . . 1.0 . .
C C26 1.2527(2) 0.53012(19) 0.76990(13) 0.0173(4) Uani d . . . 1.0 . .
H H26 1.3646 0.4649 0.7534 0.021 Uiso calc U . R 1.0 . .
C C27 0.8929(3) 1.01319(19) 0.76705(15) 0.0246(4) Uani d . . . 1.0 . .
H H27A 0.7799 0.9971 0.7523 0.037 Uiso calc U . R 1.0 . .
H H27B 0.8966 1.1074 0.7383 0.037 Uiso calc U . R 1.0 . .
H H27C 0.9009 1.0065 0.839 0.037 Uiso calc U . R 1.0 . .
C C28 1.0123(3) 0.2924(2) 0.90041(14) 0.0234(4) Uani d . . . 1.0 . .
H H28A 0.9769 0.3335 0.9638 0.035 Uiso calc U . R 1.0 . .
H H28B 1.0515 0.1892 0.9123 0.035 Uiso calc U . R 1.0 . .
H H28C 0.9096 0.3209 0.8584 0.035 Uiso calc U . R 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.286(2) ?
N1 C9 . 1.387(2) ?
N2 C4 . 1.313(2) ?
N2 H1 . 0.89(3) ?
N2 H2 . 0.90(3) ?
N3 C4 . 1.365(2) ?
N3 C2 . 1.403(2) ?
N3 C21 . 1.452(2) ?
O1 C22 . 1.372(2) ?
O1 C27 . 1.436(2) ?
O2 C25 . 1.374(2) ?
O2 C28 . 1.431(2) ?
O3 H3 . 0.85(3) ?
O3 H4 . 0.90(4) ?
O3 H4A . 0.90(4) ?
C2 C11 . 1.484(3) ?
C4 C10 . 1.440(3) ?
C5 C6 . 1.373(3) ?
C5 C10 . 1.406(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.403(3) ?
C6 H6 . 0.95 ?
C7 C8 . 1.372(3) ?
C7 H7 . 0.95 ?
C8 C9 . 1.398(3) ?
C8 H8 . 0.95 ?
C9 C10 . 1.409(3) ?
C11 C16 . 1.387(3) ?
C11 C12 . 1.392(3) ?
C12 C13 . 1.384(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.378(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.389(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.385(3) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C21 C26 . 1.384(3) ?
C21 C22 . 1.397(3) ?
C22 C23 . 1.385(3) ?
C23 C24 . 1.391(3) ?
C23 H23 . 0.95 ?
C24 C25 . 1.386(3) ?
C24 H24 . 0.95 ?
C25 C26 . 1.389(3) ?
C26 H26 . 0.95 ?
C27 H27A . 0.98 ?
C27 H27B . 0.98 ?
C27 H27C . 0.98 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C9 . . 118.03(16) ?
C4 N2 H1 . . 119.0(15) ?
C4 N2 H2 . . 120.5(18) ?
H1 N2 H2 . . 120.(2) ?
C4 N3 C2 . . 120.64(16) ?
C4 N3 C21 . . 120.09(14) ?
C2 N3 C21 . . 119.10(14) ?
C22 O1 C27 . . 116.13(15) ?
C25 O2 C28 . . 116.26(14) ?
H3 O3 H4 . . 101.(4) ?
H3 O3 H4A . . 101.(4) ?
N1 C2 N3 . . 123.91(16) ?
N1 C2 C11 . . 118.51(16) ?
N3 C2 C11 . . 117.53(16) ?
N2 C4 N3 . . 119.55(18) ?
N2 C4 C10 . . 123.23(17) ?
N3 C4 C10 . . 117.22(16) ?
C6 C5 C10 . . 119.84(18) ?
C6 C5 H5 . . 120.1 ?
C10 C5 H5 . . 120.1 ?
C5 C6 C7 . . 120.41(18) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
C8 C7 C6 . . 120.41(19) ?
C8 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
C7 C8 C9 . . 120.19(18) ?
C7 C8 H8 . . 119.9 ?
C9 C8 H8 . . 119.9 ?
N1 C9 C8 . . 118.25(17) ?
N1 C9 C10 . . 122.14(18) ?
C8 C9 C10 . . 119.55(18) ?
C5 C10 C9 . . 119.59(18) ?
C5 C10 C4 . . 122.71(17) ?
C9 C10 C4 . . 117.70(17) ?
C16 C11 C12 . . 119.68(17) ?
C16 C11 C2 . . 120.65(16) ?
C12 C11 C2 . . 119.30(16) ?
C13 C12 C11 . . 119.93(17) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C14 C13 C12 . . 120.49(18) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C15 . . 119.64(18) ?
C13 C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
C16 C15 C14 . . 120.28(18) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C15 C16 C11 . . 119.94(18) ?
C15 C16 H16 . . 120.0 ?
C11 C16 H16 . . 120.0 ?
C26 C21 C22 . . 121.86(17) ?
C26 C21 N3 . . 119.91(16) ?
C22 C21 N3 . . 118.23(16) ?
O1 C22 C23 . . 125.19(16) ?
O1 C22 C21 . . 116.56(16) ?
C23 C22 C21 . . 118.25(16) ?
C22 C23 C24 . . 120.32(17) ?
C22 C23 H23 . . 119.8 ?
C24 C23 H23 . . 119.8 ?
C25 C24 C23 . . 120.75(18) ?
C25 C24 H24 . . 119.6 ?
C23 C24 H24 . . 119.6 ?
O2 C25 C24 . . 123.94(17) ?
O2 C25 C26 . . 116.47(16) ?
C24 C25 C26 . . 119.59(17) ?
C21 C26 C25 . . 119.20(17) ?
C21 C26 H26 . . 120.4 ?
C25 C26 H26 . . 120.4 ?
O1 C27 H27A . . 109.5 ?
O1 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
O1 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
O2 C28 H28A . . 109.5 ?
O2 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
O2 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 C2 N3 . . . . -4.0(3) ?
C9 N1 C2 C11 . . . . 173.44(15) ?
C4 N3 C2 N1 . . . . 1.6(3) ?
C21 N3 C2 N1 . . . . -173.76(16) ?
C4 N3 C2 C11 . . . . -175.89(15) ?
C21 N3 C2 C11 . . . . 8.8(2) ?
C2 N3 C4 N2 . . . . -175.76(16) ?
C21 N3 C4 N2 . . . . -0.5(2) ?
C2 N3 C4 C10 . . . . 3.9(2) ?
C21 N3 C4 C10 . . . . 179.17(15) ?
C10 C5 C6 C7 . . . . -1.3(3) ?
C5 C6 C7 C8 . . . . 0.6(3) ?
C6 C7 C8 C9 . . . . 0.6(3) ?
C2 N1 C9 C8 . . . . -176.24(17) ?
C2 N1 C9 C10 . . . . 0.9(3) ?
C7 C8 C9 N1 . . . . 176.03(18) ?
C7 C8 C9 C10 . . . . -1.2(3) ?
C6 C5 C10 C9 . . . . 0.7(3) ?
C6 C5 C10 C4 . . . . 179.70(17) ?
N1 C9 C10 C5 . . . . -176.56(16) ?
C8 C9 C10 C5 . . . . 0.5(3) ?
N1 C9 C10 C4 . . . . 4.4(3) ?
C8 C9 C10 C4 . . . . -178.53(16) ?
N2 C4 C10 C5 . . . . -5.9(3) ?
N3 C4 C10 C5 . . . . 174.43(16) ?
N2 C4 C10 C9 . . . . 173.08(17) ?
N3 C4 C10 C9 . . . . -6.5(2) ?
N1 C2 C11 C16 . . . . 64.7(2) ?
N3 C2 C11 C16 . . . . -117.71(19) ?
N1 C2 C11 C12 . . . . -108.3(2) ?
N3 C2 C11 C12 . . . . 69.3(2) ?
C16 C11 C12 C13 . . . . -0.1(3) ?
C2 C11 C12 C13 . . . . 172.91(17) ?
C11 C12 C13 C14 . . . . 1.8(3) ?
C12 C13 C14 C15 . . . . -1.6(3) ?
C13 C14 C15 C16 . . . . -0.3(3) ?
C14 C15 C16 C11 . . . . 1.9(3) ?
C12 C11 C16 C15 . . . . -1.7(3) ?
C2 C11 C16 C15 . . . . -174.65(19) ?
C4 N3 C21 C26 . . . . 78.7(2) ?
C2 N3 C21 C26 . . . . -105.90(19) ?
C4 N3 C21 C22 . . . . -101.58(19) ?
C2 N3 C21 C22 . . . . 73.8(2) ?
C27 O1 C22 C23 . . . . 13.5(2) ?
C27 O1 C22 C21 . . . . -166.34(15) ?
C26 C21 C22 O1 . . . . -178.53(15) ?
N3 C21 C22 O1 . . . . 1.8(2) ?
C26 C21 C22 C23 . . . . 1.6(3) ?
N3 C21 C22 C23 . . . . -178.08(15) ?
O1 C22 C23 C24 . . . . 178.51(16) ?
C21 C22 C23 C24 . . . . -1.6(3) ?
C22 C23 C24 C25 . . . . 0.1(3) ?
C28 O2 C25 C24 . . . . 6.3(2) ?
C28 O2 C25 C26 . . . . -173.97(15) ?
C23 C24 C25 O2 . . . . -178.81(16) ?
C23 C24 C25 C26 . . . . 1.5(3) ?
C22 C21 C26 C25 . . . . 0.0(3) ?
N3 C21 C26 C25 . . . . 179.65(15) ?
O2 C25 C26 C21 . . . . 178.76(15) ?
C24 C25 C26 C21 . . . . -1.5(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H1 Cl1 . 0.89(3) 2.35(3) 3.2209(18) 165.(2) ?
N2 H2 O3 . 0.90(3) 1.93(3) 2.769(2) 154.(3) ?
O3 H3 Cl1 2_766 0.85(3) 2.28(3) 3.1126(17) 165.(2) ?
O3 H4 O3 2_766 0.90(4) 1.93(4) 2.828(3) 171.(5) ?

