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

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

data_436
_database_code_depnum_ccdc_archive 'CCDC 1407107'
_audit_update_record             
;
2015-06-16 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
_audit_creation_date             2015-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H21 N2, Br, 0.5(H2 O)'
_chemical_formula_sum            'C28 H22.50 Br N2 O0.50'
_chemical_formula_weight         474.89
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C28 H21 Br N2'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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                   9.9409(5)
_cell_length_b                   10.7823(5)
_cell_length_c                   11.4682(6)
_cell_angle_alpha                67.893(5)
_cell_angle_beta                 76.899(5)
_cell_angle_gamma                87.268(4)
_cell_volume                     1108.25(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4118
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5100
_cell_measurement_theta_min      3.1830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.875
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             487
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9310
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.994
_diffrn_reflns_theta_min         2.818
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -36.00   47.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777   57.0000  -60.0000 83

#__ type_ start__ end____ width___ exp.time_
  2 omega  -13.00   23.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00    0.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega   -1.00   86.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   57.0000 -120.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega   -7.00   81.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   38.0000   60.0000 88

#__ type_ start__ end____ width___ exp.time_
  6 omega  -51.00   42.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -77.0000  120.0000 93
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0475405000
_diffrn_orient_matrix_UB_12      -0.0002396000
_diffrn_orient_matrix_UB_13      -0.0376387000
_diffrn_orient_matrix_UB_21      -0.0429148000
_diffrn_orient_matrix_UB_22      -0.0482219000
_diffrn_orient_matrix_UB_23      0.0550779000
_diffrn_orient_matrix_UB_31      -0.0356991000
_diffrn_orient_matrix_UB_32      0.0522008000
_diffrn_orient_matrix_UB_33      0.0156564000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4050
_reflns_number_total             4771
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4771
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+1.4940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1109
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1-H1A
 0.85 with sigma of 0.02
 H1A-H1B
 1.5 with sigma of 0.02
3. Others
 Fixed Sof: O1(0.5) H1A(0.5) H1B(0.5)
4.a Free rotating group:
 O1(H1A,H1B)
4.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
4.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C20(H20), C26(H26), C3(H3), C1(H1), C28(H28), C10(H10), C8(H8),
 C17(H17), C7(H7), C24(H24), C15(H15), C27(H27), C2(H2), C16(H16), C25(H25),
 C19(H19), C4(H4), C18(H18)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3056(2) 0.4597(2) 0.4979(2) 0.0152(5) Uani 1 1 d . . . . .
N2 N 0.2418(2) 0.7745(2) 0.5273(2) 0.0147(5) Uani 1 1 d . . . . .
C9 C 0.3662(3) 0.5246(4) 0.9002(3) 0.0328(8) Uani 1 1 d . . . . .
H9 H 0.3678 0.5543 0.9662 0.039 Uiso 1 1 calc R . . . .
C23 C 0.1678(3) 0.6841(3) 0.2687(3) 0.0141(5) Uani 1 1 d . . . . .
C22 C 0.2618(3) 0.5893(3) 0.4846(3) 0.0129(5) Uani 1 1 d . . . . .
C21 C 0.2088(3) 0.6878(3) 0.3843(2) 0.0133(5) Uani 1 1 d . . . . .
C12 C 0.2779(3) 0.6433(3) 0.5742(3) 0.0137(5) Uani 1 1 d . . . . .
C20 C 0.2012(3) 0.7993(3) 0.4145(3) 0.0161(6) Uani 1 1 d . . . . .
H20 H 0.1721 0.8815 0.3649 0.019 Uiso 1 1 calc R . . . .
C26 C 0.0914(3) 0.6841(3) 0.0497(3) 0.0247(7) Uani 1 1 d . . . . .
H26 H 0.0659 0.6840 -0.0235 0.030 Uiso 1 1 calc R . . . .
C14 C 0.1149(3) 0.8825(3) 0.6768(3) 0.0168(6) Uani 1 1 d . . . . .
C3 C 0.3981(3) 0.2100(3) 0.5143(4) 0.0324(8) Uani 1 1 d . . . . .
H3 H 0.4279 0.1250 0.5209 0.039 Uiso 1 1 calc R . . . .
C1 C 0.3047(3) 0.4143(3) 0.4007(3) 0.0217(6) Uani 1 1 d . . . . .
H1 H 0.2726 0.4692 0.3288 0.026 Uiso 1 1 calc R . . . .
C28 C 0.2406(3) 0.7649(3) 0.1455(3) 0.0158(5) Uani 1 1 d . . . . .
H28 H 0.3155 0.8189 0.1364 0.019 Uiso 1 1 calc R . . . .
C5 C 0.3549(3) 0.3820(3) 0.6045(3) 0.0194(6) Uani 1 1 d . . . . .
C10 C 0.3268(3) 0.6094(3) 0.7903(3) 0.0234(6) Uani 1 1 d . . . . .
H10 H 0.3034 0.6963 0.7823 0.028 Uiso 1 1 calc R . . . .
C8 C 0.4036(3) 0.3951(4) 0.9130(3) 0.0362(9) Uani 1 1 d . . . . .
H8 H 0.4315 0.3391 0.9869 0.043 Uiso 1 1 calc R . . . .
C17 C -0.1218(3) 0.9042(3) 0.8525(3) 0.0263(7) Uani 1 1 d . . . . .
H17 H -0.2008 0.9118 0.9106 0.032 Uiso 1 1 calc R . . . .
C7 C 0.3997(3) 0.3493(3) 0.8175(3) 0.0303(8) Uani 1 1 d . . . . .
H7 H 0.4239 0.2620 0.8276 0.036 Uiso 1 1 calc R . . . .
C24 C 0.0560(3) 0.6036(3) 0.2804(3) 0.0238(7) Uani 1 1 d . . . . .
H24 H 0.0061 0.5497 0.3619 0.029 Uiso 1 1 calc R . . . .
C6 C 0.3593(3) 0.4329(3) 0.7036(3) 0.0196(6) Uani 1 1 d . . . . .
C15 C 0.1148(3) 0.9691(3) 0.7408(3) 0.0197(6) Uani 1 1 d . . . . .
H15 H 0.1945 1.0201 0.7254 0.024 Uiso 1 1 calc R . . . .
C27 C 0.2017(3) 0.7650(3) 0.0366(3) 0.0211(6) Uani 1 1 d . . . . .
H27 H 0.2500 0.8197 -0.0452 0.025 Uiso 1 1 calc R . . . .
C2 C 0.3496(3) 0.2914(3) 0.4071(4) 0.0288(7) Uani 1 1 d . . . . .
H2 H 0.3479 0.2622 0.3407 0.035 Uiso 1 1 calc R . . . .
C13 C 0.2450(3) 0.8796(3) 0.5784(3) 0.0175(6) Uani 1 1 d . . . . .
H13A H 0.2590 0.9658 0.5070 0.021 Uiso 1 1 calc R . . . .
H13B H 0.3234 0.8672 0.6183 0.021 Uiso 1 1 calc R . . . .
C11 C 0.3217(3) 0.5657(3) 0.6901(3) 0.0167(6) Uani 1 1 d . . . . .
C16 C -0.0031(3) 0.9805(3) 0.8278(3) 0.0240(7) Uani 1 1 d . . . . .
H16 H -0.0022 1.0395 0.8694 0.029 Uiso 1 1 calc R . . . .
C25 C 0.0187(3) 0.6035(4) 0.1707(3) 0.0282(7) Uani 1 1 d . . . . .
H25 H -0.0554 0.5490 0.1789 0.034 Uiso 1 1 calc R . . . .
C19 C -0.0046(3) 0.8059(3) 0.7020(3) 0.0228(6) Uani 1 1 d . . . . .
H19 H -0.0062 0.7473 0.6600 0.027 Uiso 1 1 calc R . . . .
C4 C 0.4019(3) 0.2548(3) 0.6093(4) 0.0293(8) Uani 1 1 d . . . . .
H4 H 0.4364 0.2002 0.6797 0.035 Uiso 1 1 calc R . . . .
C18 C -0.1222(3) 0.8172(3) 0.7905(3) 0.0282(7) Uani 1 1 d . . . . .
H18 H -0.2017 0.7652 0.8077 0.034 Uiso 1 1 calc R . . . .
Br1 Br 0.48317(3) 0.07510(3) 0.24066(3) 0.02844(12) Uani 1 1 d . . . . .
O1 O 0.4355(5) 0.0545(5) 0.9646(4) 0.0283(10) Uani 0.5 1 d D . P . .
H1A H 0.3528 0.0588 0.9703 0.043 Uiso 0.5 1 d DG . P . .
H1B H 0.4794 0.0244 1.0245 0.043 Uiso 0.5 1 d DG . P . .


_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 C22 1.406(3) . ?
N1 C1 1.378(4) . ?
N1 C5 1.378(4) . ?
N2 C12 1.373(3) . ?
N2 C20 1.368(3) . ?
N2 C13 1.463(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(4) . ?
C9 C8 1.390(6) . ?
C23 C21 1.488(4) . ?
C23 C28 1.396(4) . ?
C23 C24 1.394(4) . ?
C22 C21 1.425(4) . ?
C22 C12 1.398(4) . ?
C21 C20 1.365(4) . ?
C12 C11 1.430(4) . ?
C20 H20 0.9300 . ?
C26 H26 0.9300 . ?
C26 C27 1.380(4) . ?
C26 C25 1.378(4) . ?
C14 C15 1.389(4) . ?
C14 C13 1.518(4) . ?
C14 C19 1.391(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.390(5) . ?
C3 C4 1.356(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.359(4) . ?
C28 H28 0.9300 . ?
C28 C27 1.388(4) . ?
C5 C6 1.445(4) . ?
C5 C4 1.413(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.408(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.369(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.384(5) . ?
C17 C18 1.375(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.413(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.390(4) . ?
C6 C11 1.422(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(4) . ?
C27 H27 0.9300 . ?
C2 H2 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C16 H16 0.9300 . ?
C25 H25 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.398(4) . ?
C4 H4 0.9300 . ?
C18 H18 0.9300 . ?
O1 O1 1.816(9) 2_657 ?
O1 H1A 0.8104 . ?
O1 H1B 0.8500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C22 119.3(2) . . ?
C1 N1 C5 120.7(2) . . ?
C5 N1 C22 119.9(2) . . ?
C12 N2 C13 130.0(2) . . ?
C20 N2 C12 108.6(2) . . ?
C20 N2 C13 121.4(2) . . ?
C10 C9 H9 119.7 . . ?
C10 C9 C8 120.5(3) . . ?
C8 C9 H9 119.7 . . ?
C28 C23 C21 119.6(2) . . ?
C24 C23 C21 121.5(2) . . ?
C24 C23 C28 118.9(2) . . ?
N1 C22 C21 130.4(2) . . ?
C12 C22 N1 120.1(2) . . ?
C12 C22 C21 109.3(2) . . ?
C22 C21 C23 132.4(2) . . ?
C20 C21 C23 123.3(2) . . ?
C20 C21 C22 104.3(2) . . ?
N2 C12 C22 106.3(2) . . ?
N2 C12 C11 131.3(3) . . ?
C22 C12 C11 122.4(2) . . ?
N2 C20 H20 124.3 . . ?
C21 C20 N2 111.3(2) . . ?
C21 C20 H20 124.3 . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.3(3) . . ?
C15 C14 C13 118.0(2) . . ?
C15 C14 C19 118.9(3) . . ?
C19 C14 C13 123.0(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.8(3) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 N1 121.6(3) . . ?
C2 C1 H1 119.2 . . ?
C23 C28 H28 119.8 . . ?
C27 C28 C23 120.4(3) . . ?
C27 C28 H28 119.8 . . ?
N1 C5 C6 120.0(2) . . ?
N1 C5 C4 116.9(3) . . ?
C4 C5 C6 123.1(3) . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C8 H8 119.8 . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C18 C17 C16 119.5(3) . . ?
C8 C7 H7 119.6 . . ?
C8 C7 C6 120.8(3) . . ?
C6 C7 H7 119.6 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.9 . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 C11 118.8(3) . . ?
C11 C6 C5 121.3(3) . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.7(3) . . ?
C16 C15 H15 119.7 . . ?
C26 C27 C28 120.0(3) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C3 C2 H2 120.5 . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H2 120.5 . . ?
N2 C13 C14 114.2(2) . . ?
N2 C13 H13A 108.7 . . ?
N2 C13 H13B 108.7 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C10 C11 C12 125.4(3) . . ?
C10 C11 C6 118.8(3) . . ?
C6 C11 C12 115.8(3) . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C26 C25 C24 120.1(3) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C14 C19 H19 120.0 . . ?
C14 C19 C18 119.9(3) . . ?
C18 C19 H19 120.0 . . ?
C3 C4 C5 122.0(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C17 C18 C19 120.7(3) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
O1 O1 H1A 141.7 2_657 . ?
O1 O1 H1B 30.3 2_657 . ?
H1A O1 H1B 128.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C22 C21 C23 7.6(5) . . . . ?
N1 C22 C21 C20 -172.3(3) . . . . ?
N1 C22 C12 N2 172.9(2) . . . . ?
N1 C22 C12 C11 -8.2(4) . . . . ?
N1 C1 C2 C3 -0.3(4) . . . . ?
N1 C5 C6 C7 175.1(2) . . . . ?
N1 C5 C6 C11 -4.0(4) . . . . ?
N1 C5 C4 C3 -0.5(4) . . . . ?
N2 C12 C11 C10 5.4(5) . . . . ?
N2 C12 C11 C6 -176.3(3) . . . . ?
C9 C10 C11 C12 177.7(3) . . . . ?
C9 C10 C11 C6 -0.6(4) . . . . ?
C9 C8 C7 C6 0.8(5) . . . . ?
C23 C21 C20 N2 178.5(2) . . . . ?
C23 C28 C27 C26 -0.6(4) . . . . ?
C23 C24 C25 C26 -0.7(5) . . . . ?
C22 N1 C1 C2 178.2(3) . . . . ?
C22 N1 C5 C6 1.0(4) . . . . ?
C22 N1 C5 C4 -177.7(2) . . . . ?
C22 C21 C20 N2 -1.7(3) . . . . ?
C22 C12 C11 C10 -173.2(3) . . . . ?
C22 C12 C11 C6 5.1(4) . . . . ?
C21 C23 C28 C27 -178.5(3) . . . . ?
C21 C23 C24 C25 179.0(3) . . . . ?
C21 C22 C12 N2 -2.7(3) . . . . ?
C21 C22 C12 C11 176.2(2) . . . . ?
C12 N2 C20 C21 0.1(3) . . . . ?
C12 N2 C13 C14 -87.0(3) . . . . ?
C12 C22 C21 C23 -177.5(3) . . . . ?
C12 C22 C21 C20 2.7(3) . . . . ?
C20 N2 C12 C22 1.6(3) . . . . ?
C20 N2 C12 C11 -177.2(3) . . . . ?
C20 N2 C13 C14 94.5(3) . . . . ?
C14 C15 C16 C17 0.6(4) . . . . ?
C14 C19 C18 C17 0.6(5) . . . . ?
C1 N1 C22 C21 2.4(4) . . . . ?
C1 N1 C22 C12 -172.1(2) . . . . ?
C1 N1 C5 C6 178.0(2) . . . . ?
C1 N1 C5 C4 -0.8(4) . . . . ?
C28 C23 C21 C22 -116.1(3) . . . . ?
C28 C23 C21 C20 63.7(4) . . . . ?
C28 C23 C24 C25 0.5(4) . . . . ?
C5 N1 C22 C21 179.4(3) . . . . ?
C5 N1 C22 C12 4.9(4) . . . . ?
C5 N1 C1 C2 1.2(4) . . . . ?
C5 C6 C11 C12 1.0(4) . . . . ?
C5 C6 C11 C10 179.4(2) . . . . ?
C10 C9 C8 C7 -1.0(5) . . . . ?
C8 C9 C10 C11 1.0(5) . . . . ?
C8 C7 C6 C5 -179.5(3) . . . . ?
C8 C7 C6 C11 -0.4(4) . . . . ?
C7 C6 C11 C12 -178.2(2) . . . . ?
C7 C6 C11 C10 0.3(4) . . . . ?
C24 C23 C21 C22 65.4(4) . . . . ?
C24 C23 C21 C20 -114.8(3) . . . . ?
C24 C23 C28 C27 0.1(4) . . . . ?
C6 C5 C4 C3 -179.2(3) . . . . ?
C15 C14 C13 N2 173.0(2) . . . . ?
C15 C14 C19 C18 0.1(4) . . . . ?
C27 C26 C25 C24 0.2(5) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C13 N2 C12 C22 -177.0(3) . . . . ?
C13 N2 C12 C11 4.2(5) . . . . ?
C13 N2 C20 C21 178.9(2) . . . . ?
C13 C14 C15 C16 177.2(3) . . . . ?
C13 C14 C19 C18 -177.7(3) . . . . ?
C16 C17 C18 C19 -0.6(5) . . . . ?
C25 C26 C27 C28 0.4(5) . . . . ?
C19 C14 C15 C16 -0.7(4) . . . . ?
C19 C14 C13 N2 -9.2(4) . . . . ?
C4 C3 C2 C1 -1.0(5) . . . . ?
C4 C5 C6 C7 -6.2(4) . . . . ?
C4 C5 C6 C11 174.7(3) . . . . ?
C18 C17 C16 C15 0.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ole_392
_database_code_depnum_ccdc_archive 'CCDC 1407108'
_audit_update_record             
;
2015-06-16 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
_audit_creation_date             2015-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 N2, C H4 O, I'
_chemical_formula_sum            'C23 H21 I N2 O'
_chemical_formula_weight         468.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H17 I N2'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.5184(9)
_cell_length_b                   8.2523(2)
_cell_length_c                   18.6675(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.173(3)
_cell_angle_gamma                90
_cell_volume                     3923.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5040
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.7380
_cell_measurement_theta_min      3.1930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11477
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.594
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -22.00   24.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
  2 omega  -13.00   12.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega   70.00   95.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152 -178.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega    3.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   38.0000 -150.0000 88

#__ type_ start__ end____ width___ exp.time_
  5 omega    2.00   78.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152    0.0000  150.0000 76

#__ type_ start__ end____ width___ exp.time_
  6 omega  -45.00   -6.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -57.0000 -180.0000 39
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0065936000
_diffrn_orient_matrix_UB_12      -0.0834292000
_diffrn_orient_matrix_UB_13      -0.0039649000
_diffrn_orient_matrix_UB_21      0.0269351000
_diffrn_orient_matrix_UB_22      -0.0205760000
_diffrn_orient_matrix_UB_23      0.0137792000
_diffrn_orient_matrix_UB_31      -0.0024624000
_diffrn_orient_matrix_UB_32      -0.0012685000
_diffrn_orient_matrix_UB_33      0.0368895000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3831
_reflns_number_total             4420
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4420
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0193P)²+5.7602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0565
_refine_ls_wR_factor_ref         0.0598
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C14(H14),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C23(H23A,H23B,H23C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.67528(8) 0.1780(2) 0.39347(10) 0.0139(4) Uani 1 1 d . . . . .
N2 N 0.68977(8) -0.0449(3) 0.56061(10) 0.0165(4) Uani 1 1 d . . . . .
C1 C 0.63464(10) 0.2666(3) 0.34886(13) 0.0180(5) Uani 1 1 d . . . . .
H1 H 0.6022 0.2662 0.3590 0.022 Uiso 1 1 calc R . . . .
C2 C 0.64075(10) 0.3549(3) 0.29007(13) 0.0202(5) Uani 1 1 d . . . . .
H2 H 0.6129 0.4149 0.2606 0.024 Uiso 1 1 calc R . . . .
C3 C 0.68910(11) 0.3541(3) 0.27484(13) 0.0212(6) Uani 1 1 d . . . . .
H3 H 0.6939 0.4124 0.2346 0.025 Uiso 1 1 calc R . . . .
C4 C 0.72976(10) 0.2667(3) 0.31953(13) 0.0192(5) Uani 1 1 d . . . . .
H4 H 0.7621 0.2672 0.3092 0.023 Uiso 1 1 calc R . . . .
C5 C 0.72392(10) 0.1767(3) 0.38042(13) 0.0152(5) Uani 1 1 d . . . . .
C6 C 0.76665(9) 0.0868(3) 0.43010(12) 0.0150(5) Uani 1 1 d . . . . .
C7 C 0.81661(10) 0.0825(3) 0.41662(14) 0.0201(5) Uani 1 1 d . . . . .
H7 H 0.8220 0.1397 0.3765 0.024 Uiso 1 1 calc R . . . .
C8 C 0.85711(10) -0.0046(3) 0.46167(14) 0.0237(6) Uani 1 1 d . . . . .
H8 H 0.8895 -0.0071 0.4516 0.028 Uiso 1 1 calc R . . . .
C9 C 0.84988(10) -0.0894(3) 0.52259(14) 0.0224(6) Uani 1 1 d . . . . .
H9 H 0.8774 -0.1492 0.5527 0.027 Uiso 1 1 calc R . . . .
C10 C 0.80232(10) -0.0852(3) 0.53861(13) 0.0187(5) Uani 1 1 d . . . . .
H10 H 0.7982 -0.1413 0.5798 0.022 Uiso 1 1 calc R . . . .
C11 C 0.75984(9) 0.0030(3) 0.49330(12) 0.0143(5) Uani 1 1 d . . . . .
C12 C 0.70872(9) 0.0133(3) 0.50397(12) 0.0140(5) Uani 1 1 d . . . . .
C13 C 0.71636(10) -0.1421(3) 0.62577(13) 0.0200(5) Uani 1 1 d . . . . .
H13A H 0.7228 -0.2489 0.6100 0.030 Uiso 1 1 calc GR . . . .
H13B H 0.6946 -0.1492 0.6590 0.030 Uiso 1 1 calc GR . . . .
H13C H 0.7491 -0.0918 0.6511 0.030 Uiso 1 1 calc GR . . . .
C14 C 0.63758(9) -0.0089(3) 0.54427(12) 0.0177(5) Uani 1 1 d . . . . .
H14 H 0.6163 -0.0354 0.5746 0.021 Uiso 1 1 calc R . . . .
C15 C 0.62047(10) 0.0710(3) 0.47784(12) 0.0160(5) Uani 1 1 d . . . . .
C16 C 0.66664(9) 0.0888(3) 0.45322(12) 0.0146(5) Uani 1 1 d . . . . .
C17 C 0.56458(10) 0.1123(3) 0.44323(13) 0.0180(5) Uani 1 1 d . . . . .
C18 C 0.53797(11) 0.0522(4) 0.37302(14) 0.0281(6) Uani 1 1 d . . . . .
H18 H 0.5556 -0.0126 0.3470 0.034 Uiso 1 1 calc R . . . .
C19 C 0.48542(11) 0.0886(4) 0.34186(15) 0.0374(8) Uani 1 1 d . . . . .
H19 H 0.4679 0.0475 0.2952 0.045 Uiso 1 1 calc R . . . .
C20 C 0.45917(12) 0.1848(4) 0.37939(18) 0.0390(8) Uani 1 1 d . . . . .
H20 H 0.4242 0.2120 0.3576 0.047 Uiso 1 1 calc R . . . .
C21 C 0.48485(12) 0.2411(4) 0.44971(18) 0.0385(8) Uani 1 1 d . . . . .
H21 H 0.4667 0.3039 0.4757 0.046 Uiso 1 1 calc R . . . .
C22 C 0.53719(11) 0.2050(3) 0.48189(16) 0.0272(6) Uani 1 1 d . . . . .
H22 H 0.5540 0.2430 0.5294 0.033 Uiso 1 1 calc R . . . .
O1 O 0.43733(9) 0.5807(3) 0.35302(12) 0.0453(6) Uani 1 1 d . . . . .
H1A H 0.4179 0.6488 0.3274 0.068 Uiso 1 1 calc GR . . . .
C23 C 0.48889(17) 0.6051(6) 0.3487(2) 0.0702(13) Uani 1 1 d . . . . .
H23A H 0.4891 0.6048 0.2973 0.105 Uiso 1 1 calc GR . . . .
H23B H 0.5111 0.5197 0.3749 0.105 Uiso 1 1 calc GR . . . .
H23C H 0.5017 0.7074 0.3708 0.105 Uiso 1 1 calc GR . . . .
I1 I 0.65081(2) 0.15762(2) 0.76341(2) 0.02011(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.375(3) . ?
N1 C5 1.378(3) . ?
N1 C16 1.407(3) . ?
N2 C12 1.377(3) . ?
N2 C13 1.463(3) . ?
N2 C14 1.364(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.364(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.370(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.402(3) . ?
C5 C6 1.452(3) . ?
C6 C7 1.416(3) . ?
C6 C11 1.422(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.369(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.393(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.375(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.409(3) . ?
C11 C12 1.427(3) . ?
C12 C16 1.393(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C15 1.366(3) . ?
C15 C16 1.430(3) . ?
C15 C17 1.482(3) . ?
C17 C18 1.395(4) . ?
C17 C22 1.388(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.385(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.370(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.383(4) . ?
C22 H22 0.9300 . ?
O1 H1A 0.8200 . ?
O1 C23 1.406(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 120.8(2) . . ?
C1 N1 C16 119.0(2) . . ?
C5 N1 C16 120.2(2) . . ?
C12 N2 C13 129.4(2) . . ?
C14 N2 C12 108.46(19) . . ?
C14 N2 C13 121.9(2) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 N1 121.5(2) . . ?
C2 C1 H1 119.2 . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.8(2) . . ?
C5 C4 H4 119.1 . . ?
N1 C5 C4 117.3(2) . . ?
N1 C5 C6 119.6(2) . . ?
C4 C5 C6 123.1(2) . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 C11 118.5(2) . . ?
C11 C6 C5 121.4(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.7(2) . . ?
C11 C10 H10 119.6 . . ?
C6 C11 C12 115.6(2) . . ?
C10 C11 C6 119.0(2) . . ?
C10 C11 C12 125.4(2) . . ?
N2 C12 C11 130.6(2) . . ?
N2 C12 C16 106.5(2) . . ?
C16 C12 C11 122.9(2) . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14 124.2 . . ?
N2 C14 C15 111.6(2) . . ?
C15 C14 H14 124.2 . . ?
C14 C15 C16 104.1(2) . . ?
C14 C15 C17 123.1(2) . . ?
C16 C15 C17 132.7(2) . . ?
N1 C16 C15 130.7(2) . . ?
C12 C16 N1 119.8(2) . . ?
C12 C16 C15 109.3(2) . . ?
C18 C17 C15 120.7(2) . . ?
C22 C17 C15 120.3(2) . . ?
C22 C17 C18 118.9(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C21 119.7(3) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.7(3) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 H22 120.0 . . ?
C21 C22 C17 120.0(3) . . ?
C21 C22 H22 120.0 . . ?
C23 O1 H1A 109.5 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
N1 C1 C2 C3 0.5(4) . . . . ?
N1 C5 C6 C7 179.0(2) . . . . ?
N1 C5 C6 C11 -1.6(3) . . . . ?
N2 C12 C16 N1 172.2(2) . . . . ?
N2 C12 C16 C15 -2.2(3) . . . . ?
N2 C14 C15 C16 -1.8(3) . . . . ?
N2 C14 C15 C17 174.6(2) . . . . ?
C1 N1 C5 C4 -1.0(3) . . . . ?
C1 N1 C5 C6 177.7(2) . . . . ?
C1 N1 C16 C12 -172.8(2) . . . . ?
C1 N1 C16 C15 0.3(4) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 N1 0.6(3) . . . . ?
C3 C4 C5 C6 -178.1(2) . . . . ?
C4 C5 C6 C7 -2.3(4) . . . . ?
C4 C5 C6 C11 177.0(2) . . . . ?
C5 N1 C1 C2 0.5(3) . . . . ?
C5 N1 C16 C12 6.9(3) . . . . ?
C5 N1 C16 C15 180.0(2) . . . . ?
C5 C6 C7 C8 -178.4(2) . . . . ?
C5 C6 C11 C10 178.6(2) . . . . ?
C5 C6 C11 C12 0.2(3) . . . . ?
C6 C7 C8 C9 -0.8(4) . . . . ?
C6 C11 C12 N2 -176.1(2) . . . . ?
C6 C11 C12 C16 5.0(3) . . . . ?
C7 C6 C11 C10 -2.1(3) . . . . ?
C7 C6 C11 C12 179.5(2) . . . . ?
C7 C8 C9 C10 -0.7(4) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C9 C10 C11 C6 0.6(4) . . . . ?
C9 C10 C11 C12 178.9(2) . . . . ?
C10 C11 C12 N2 5.6(4) . . . . ?
C10 C11 C12 C16 -173.3(2) . . . . ?
C11 C6 C7 C8 2.2(4) . . . . ?
C11 C12 C16 N1 -8.7(3) . . . . ?
C11 C12 C16 C15 176.9(2) . . . . ?
C12 N2 C14 C15 0.5(3) . . . . ?
C13 N2 C12 C11 -3.0(4) . . . . ?
C13 N2 C12 C16 176.0(2) . . . . ?
C13 N2 C14 C15 -174.8(2) . . . . ?
C14 N2 C12 C11 -177.9(2) . . . . ?
C14 N2 C12 C16 1.1(3) . . . . ?
C14 C15 C16 N1 -171.1(2) . . . . ?
C14 C15 C16 C12 2.5(3) . . . . ?
C14 C15 C17 C18 -119.6(3) . . . . ?
C14 C15 C17 C22 57.2(4) . . . . ?
C15 C17 C18 C19 178.6(3) . . . . ?
C15 C17 C22 C21 -179.0(3) . . . . ?
C16 N1 C1 C2 -179.8(2) . . . . ?
C16 N1 C5 C4 179.4(2) . . . . ?
C16 N1 C5 C6 -1.9(3) . . . . ?
C16 C15 C17 C18 55.6(4) . . . . ?
C16 C15 C17 C22 -127.6(3) . . . . ?
C17 C15 C16 N1 13.0(4) . . . . ?
C17 C15 C16 C12 -173.4(3) . . . . ?
C17 C18 C19 C20 0.4(4) . . . . ?
C18 C17 C22 C21 -2.2(4) . . . . ?
C18 C19 C20 C21 -2.2(5) . . . . ?
C19 C20 C21 C22 1.7(5) . . . . ?
C20 C21 C22 C17 0.5(5) . . . . ?
C22 C17 C18 C19 1.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ole468
_database_code_depnum_ccdc_archive 'CCDC 1407277'
_audit_update_record             
;
2015-06-17 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
_audit_creation_date             2014-12-30
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H14 N2, 0.5(H2 O)'
_chemical_formula_sum            'C21 H15 N2 O0.50'
_chemical_formula_weight         303.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 N2 h18'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.5157(6)
_cell_length_b                   8.5175(2)
_cell_length_c                   19.8322(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.754(3)
_cell_angle_gamma                90.00
_cell_volume                     2943.85(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8150
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.9590
_cell_measurement_theta_min      4.4910
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            45149
_diffrn_reflns_theta_full        72.49
_diffrn_reflns_theta_max         72.49
_diffrn_reflns_theta_min         3.21
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9843
_diffrn_measured_fraction_theta_max 0.9843
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -110.00  -15.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
  2 omega  -50.00   21.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -60.0000 71

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   35.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
  4 omega   39.00   66.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   63.00   94.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
  6 omega  145.00  176.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega  104.00  131.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   57.00   86.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
  9 omega   54.00   90.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 36

#__ type_ start__ end____ width___ exp.time_
 10 omega  119.00  144.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega  109.00  142.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
 12 omega  152.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   40.00   76.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
 14 omega   30.00   59.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 29

#__ type_ start__ end____ width___ exp.time_
 15 omega   48.00   90.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 42

#__ type_ start__ end____ width___ exp.time_
 16 omega   41.00   75.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00   95.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 56

#__ type_ start__ end____ width___ exp.time_
 18 omega   58.00  146.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 88

#__ type_ start__ end____ width___ exp.time_
 19 omega   73.00  109.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
 20 omega  100.00  127.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 21 omega  143.00  168.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega   45.00   70.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega  102.00  143.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -150.0000 41

#__ type_ start__ end____ width___ exp.time_
 24 omega   52.00   77.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 25 omega  100.00  142.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
 26 omega   94.00  144.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
 27 omega  112.00  138.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega  -35.00    6.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -19.0000  -60.0000 41

#__ type_ start__ end____ width___ exp.time_
 29 omega  -93.00  -48.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -19.0000  -60.0000 45

#__ type_ start__ end____ width___ exp.time_
 30 omega   66.00  116.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   38.0000  120.0000 50

#__ type_ start__ end____ width___ exp.time_
 31 omega   28.00   56.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   38.0000  120.0000 28

#__ type_ start__ end____ width___ exp.time_
 32 omega   11.00   49.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   57.0000  -30.0000 38

#__ type_ start__ end____ width___ exp.time_
 33 omega   57.00  123.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  120.0000 66

#__ type_ start__ end____ width___ exp.time_
 34 omega   58.00  128.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -90.0000 70

#__ type_ start__ end____ width___ exp.time_
 35 omega   83.00  146.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 63

#__ type_ start__ end____ width___ exp.time_
 36 omega   83.00  115.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
 37 omega   65.00  114.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  120.0000 49

#__ type_ start__ end____ width___ exp.time_
 38 omega   90.00  165.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 75

#__ type_ start__ end____ width___ exp.time_
 39 omega  103.00  146.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
 40 omega   68.00  115.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
 41 omega   41.00   84.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 43

#__ type_ start__ end____ width___ exp.time_
 42 omega   85.00  117.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
 43 omega  149.00  176.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 44 omega   34.00   79.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   30.0000 45

#__ type_ start__ end____ width___ exp.time_
 45 omega  101.00  127.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 46 omega  151.00  176.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 47 omega   62.00  108.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
 48 omega   58.00  100.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 42

#__ type_ start__ end____ width___ exp.time_
 49 omega   58.00   87.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
 50 omega   47.00   73.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 51 omega   31.00   58.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 52 omega   85.00  111.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 53 omega  130.00  156.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 54 omega  148.00  174.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 55 omega   77.00  106.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
 56 omega   55.00  100.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 45

#__ type_ start__ end____ width___ exp.time_
 57 omega   65.00   92.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 58 omega   40.00   66.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 59 omega   96.00  121.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 60 omega  135.00  166.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
 61 omega  116.00  143.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 62 omega   43.00   69.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 63 omega   44.00   69.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 64 omega   61.00   87.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 65 omega   96.00  133.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   60.0000 37

#__ type_ start__ end____ width___ exp.time_
 66 omega   85.00  143.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
 67 omega  144.00  169.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   12.0000  -78.0145 25

#__ type_ start__ end____ width___ exp.time_
 68 omega  104.00  144.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   60.0000 40

#__ type_ start__ end____ width___ exp.time_
 69 omega   95.00  141.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
 70 omega  121.00  147.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 71 omega  137.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000    0.0000 41

#__ type_ start__ end____ width___ exp.time_
 72 omega   92.00  118.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 73 omega   30.00   56.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 74 omega   45.00   71.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   12.0000  -78.0145 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0854452000
_diffrn_orient_matrix_UB_12      -0.0378845000
_diffrn_orient_matrix_UB_13      0.0039609000
_diffrn_orient_matrix_UB_21      0.0054853000
_diffrn_orient_matrix_UB_22      -0.1358826000
_diffrn_orient_matrix_UB_23      -0.0505978000
_diffrn_orient_matrix_UB_31      0.0220268000
_diffrn_orient_matrix_UB_32      -0.1131518000
_diffrn_orient_matrix_UB_33      0.0593306000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3646
_reflns_number_total             5846
_reflns_odcompleteness_completeness 94.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     440
_refine_ls_number_reflns         5846
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0617P)²+0.9001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1499
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
C11 C 0.55516(10) 0.6237(2) 0.07540(9) 0.0330(4) Uani 1 1 d . . .
N2 N 0.50307(9) 0.77916(19) -0.04825(7) 0.0355(4) Uani 1 1 d . . .
N1 N 0.44284(9) 0.76050(18) 0.11917(7) 0.0340(3) Uani 1 1 d . . .
C6 C 0.59138(10) 0.5984(2) 0.01550(9) 0.0359(4) Uani 1 1 d . . .
C15 C 0.46582(11) 0.8029(2) 0.00957(9) 0.0333(4) Uani 1 1 d . . .
C7 C 0.65434(11) 0.4948(2) 0.01832(10) 0.0422(5) Uani 1 1 d . . .
H7 H 0.6784 0.4763 -0.0206 0.051 Uiso 1 1 calc R . .
C1 C 0.47813(12) 0.8604(2) -0.10651(9) 0.0413(5) Uani 1 1 d . . .
H1 H 0.4376 0.9308 -0.1058 0.050 Uiso 1 1 calc R . .
C5 C 0.56392(11) 0.6754(2) -0.04736(9) 0.0365(4) Uani 1 1 d . . .
C12 C 0.49013(10) 0.7255(2) 0.07097(9) 0.0322(4) Uani 1 1 d . . .
C8 C 0.68071(11) 0.4206(2) 0.07754(11) 0.0445(5) Uani 1 1 d . . .
H8 H 0.7223 0.3526 0.0785 0.053 Uiso 1 1 calc R . .
C14 C 0.40058(11) 0.8898(2) 0.02030(9) 0.0359(4) Uani 1 1 d . . .
H14 H 0.3716 0.9536 -0.0106 0.043 Uiso 1 1 calc R . .
C10 C 0.58313(11) 0.5462(2) 0.13575(10) 0.0368(4) Uani 1 1 d . . .
H10 H 0.5595 0.5622 0.1751 0.044 Uiso 1 1 calc R . .
C4 C 0.59609(12) 0.6518(3) -0.10888(10) 0.0447(5) Uani 1 1 d . . .
H4 H 0.6357 0.5795 -0.1103 0.054 Uiso 1 1 calc R . .
C16 C 0.32452(10) 0.9186(2) 0.12341(9) 0.0348(4) Uani 1 1 d . . .
C9 C 0.64504(11) 0.4472(2) 0.13655(10) 0.0416(5) Uani 1 1 d . . .
H9 H 0.6635 0.3975 0.1767 0.050 Uiso 1 1 calc R . .
C21 C 0.27884(12) 1.0430(2) 0.09625(10) 0.0421(5) Uani 1 1 d . . .
H21 H 0.2899 1.0900 0.0560 0.050 Uiso 1 1 calc R . .
C13 C 0.38832(10) 0.8598(2) 0.08782(9) 0.0340(4) Uani 1 1 d . . .
C2 C 0.51143(13) 0.8396(3) -0.16484(10) 0.0475(5) Uani 1 1 d . . .
H2 H 0.4947 0.8970 -0.2034 0.057 Uiso 1 1 calc R . .
C19 C 0.19979(12) 1.0280(3) 0.18858(11) 0.0516(6) Uani 1 1 d . . .
H19 H 0.1581 1.0631 0.2100 0.062 Uiso 1 1 calc R . .
C20 C 0.21727(12) 1.0969(3) 0.12867(11) 0.0497(5) Uani 1 1 d . . .
H20 H 0.1876 1.1797 0.1101 0.060 Uiso 1 1 calc R . .
C3 C 0.57103(12) 0.7314(3) -0.16635(10) 0.0498(6) Uani 1 1 d . . .
H3 H 0.5934 0.7139 -0.2063 0.060 Uiso 1 1 calc R . .
C17 C 0.30713(11) 0.8529(3) 0.18390(9) 0.0397(4) Uani 1 1 d . . .
H17 H 0.3374 0.7717 0.2032 0.048 Uiso 1 1 calc R . .
C18 C 0.24521(11) 0.9061(3) 0.21623(10) 0.0465(5) Uani 1 1 d . . .
H18 H 0.2342 0.8598 0.2566 0.056 Uiso 1 1 calc R . .
N2A N 0.00063(9) 0.78067(19) 0.04270(7) 0.0369(4) Uani 1 1 d . . .
N1A N 0.06177(9) 0.76317(18) -0.12445(7) 0.0351(4) Uani 1 1 d . . .
C6A C -0.08722(11) 0.6004(2) -0.02218(9) 0.0354(4) Uani 1 1 d . . .
C12A C 0.01431(10) 0.7282(2) -0.07664(9) 0.0338(4) Uani 1 1 d . . .
C5A C -0.06112(11) 0.6782(2) 0.04076(9) 0.0382(4) Uani 1 1 d . . .
C11A C -0.05077(10) 0.6271(2) -0.08176(9) 0.0335(4) Uani 1 1 d . . .
C10A C -0.07868(11) 0.5510(2) -0.14266(9) 0.0361(4) Uani 1 1 d . . .
H10A H -0.0552 0.5692 -0.1820 0.043 Uiso 1 1 calc R . .
C15A C 0.03881(11) 0.8040(2) -0.01499(9) 0.0364(4) Uani 1 1 d . . .
C9A C -0.14004(11) 0.4508(2) -0.14418(10) 0.0408(4) Uani 1 1 d . . .
H9A H -0.1582 0.4019 -0.1846 0.049 Uiso 1 1 calc R . .
C8A C -0.17544(12) 0.4215(2) -0.08532(11) 0.0441(5) Uani 1 1 d . . .
H8A H -0.2167 0.3523 -0.0866 0.053 Uiso 1 1 calc R . .
C7A C -0.14963(11) 0.4944(2) -0.02571(10) 0.0424(5) Uani 1 1 d . . .
H7A H -0.1736 0.4737 0.0131 0.051 Uiso 1 1 calc R . .
C13A C 0.11652(11) 0.8615(2) -0.09230(9) 0.0363(4) Uani 1 1 d . . .
C4A C -0.09546(12) 0.6572(3) 0.10117(10) 0.0465(5) Uani 1 1 d . . .
H4A H -0.1359 0.5867 0.1018 0.056 Uiso 1 1 calc R . .
C14A C 0.10421(11) 0.8901(2) -0.02474(9) 0.0386(4) Uani 1 1 d . . .
H14A H 0.1333 0.9526 0.0066 0.046 Uiso 1 1 calc R . .
C1A C 0.02477(12) 0.8615(2) 0.10094(9) 0.0432(5) Uani 1 1 d . . .
H1A H 0.0659 0.9305 0.1009 0.052 Uiso 1 1 calc R . .
C16A C 0.18004(11) 0.9204(2) -0.12795(10) 0.0390(4) Uani 1 1 d . . .
C2A C -0.01005(13) 0.8431(3) 0.15847(10) 0.0483(5) Uani 1 1 d . . .
H2A H 0.0066 0.9001 0.1972 0.058 Uiso 1 1 calc R . .
C21A C 0.19601(11) 0.8568(3) -0.18918(10) 0.0444(5) Uani 1 1 d . . .
H21A H 0.1647 0.7779 -0.2090 0.053 Uiso 1 1 calc R . .
C20A C 0.25806(12) 0.9088(3) -0.22146(12) 0.0527(6) Uani 1 1 d . . .
H20A H 0.2681 0.8636 -0.2623 0.063 Uiso 1 1 calc R . .
C3A C -0.07115(13) 0.7376(3) 0.15919(10) 0.0512(6) Uani 1 1 d . . .
H3A H -0.0950 0.7223 0.1985 0.061 Uiso 1 1 calc R . .
C17A C 0.22706(12) 1.0426(3) -0.10015(11) 0.0479(5) Uani 1 1 d . . .
H17A H 0.2169 1.0887 -0.0595 0.058 Uiso 1 1 calc R . .
C19A C 0.30483(13) 1.0269(3) -0.19349(13) 0.0591(7) Uani 1 1 d . . .
H19A H 0.3468 1.0607 -0.2149 0.071 Uiso 1 1 calc R . .
C18A C 0.28836(13) 1.0946(3) -0.13285(13) 0.0581(7) Uani 1 1 d . . .
H18A H 0.3189 1.1759 -0.1141 0.070 Uiso 1 1 calc R . .
O1 O 0.46679(11) 0.6358(2) 0.25161(8) 0.0339(5) Uani 0.649(3) 1 d PG A 1
H1B H 0.4981 0.6885 0.2782 0.051 Uiso 0.649(3) 1 d PG A 1
H1C H 0.4596 0.6821 0.2135 0.051 Uiso 0.649(3) 1 d PG A 1
O1A O 0.0344(3) 0.6359(6) -0.2533(2) 0.0560(13) Uani 0.351(3) 1 d PG A 2
H1AA H 0.0433 0.6697 -0.2131 0.084 Uiso 0.351(3) 1 d PG A 2
H1AB H 0.0033 0.6977 -0.2759 0.084 Uiso 0.351(3) 1 d PG A 2


_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
C11 C6 1.418(3) . ?
C11 C12 1.427(3) . ?
C11 C10 1.411(3) . ?
N2 C15 1.390(2) . ?
N2 C1 1.379(2) . ?
N2 C5 1.383(3) . ?
N1 C12 1.359(2) . ?
N1 C13 1.377(2) . ?
C6 C7 1.409(3) . ?
C6 C5 1.448(3) . ?
C15 C12 1.412(2) . ?
C15 C14 1.396(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.372(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.358(3) . ?
C5 C4 1.409(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.399(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.401(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.372(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.361(3) . ?
C16 C21 1.402(3) . ?
C16 C13 1.468(3) . ?
C16 C17 1.385(3) . ?
C9 H9 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.388(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.395(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(3) . ?
C19 C18 1.387(3) . ?
C20 H20 0.9300 . ?
C3 H3 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.390(3) . ?
C18 H18 0.9300 . ?
N2A C5A 1.387(3) . ?
N2A C15A 1.396(2) . ?
N2A C1A 1.374(2) . ?
N1A C12A 1.355(2) . ?
N1A C13A 1.380(2) . ?
C6A C5A 1.447(3) . ?
C6A C11A 1.417(3) . ?
C6A C7A 1.414(3) . ?
C12A C11A 1.424(3) . ?
C12A C15A 1.411(2) . ?
C5A C4A 1.405(3) . ?
C11A C10A 1.414(2) . ?
C10A H10A 0.9300 . ?
C10A C9A 1.371(3) . ?
C15A C14A 1.390(3) . ?
C9A H9A 0.9300 . ?
C9A C8A 1.398(3) . ?
C8A H8A 0.9300 . ?
C8A C7A 1.371(3) . ?
C7A H7A 0.9300 . ?
C13A C14A 1.400(3) . ?
C13A C16A 1.465(3) . ?
C4A H4A 0.9300 . ?
C4A C3A 1.370(3) . ?
C14A H14A 0.9300 . ?
C1A H1A 0.9300 . ?
C1A C2A 1.356(3) . ?
C16A C21A 1.384(3) . ?
C16A C17A 1.405(3) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.398(3) . ?
C21A H21A 0.9300 . ?
C21A C20A 1.388(3) . ?
C20A H20A 0.9300 . ?
C20A C19A 1.378(3) . ?
C3A H3A 0.9300 . ?
C17A H17A 0.9300 . ?
C17A C18A 1.382(3) . ?
C19A H19A 0.9300 . ?
C19A C18A 1.390(4) . ?
C18A H18A 0.9300 . ?
O1 H1B 0.8496 . ?
O1 H1C 0.8500 . ?
O1A H1AA 0.8488 . ?
O1A H1AB 0.8512 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C11 C12 117.53(16) . . ?
C10 C11 C6 119.51(18) . . ?
C10 C11 C12 122.94(17) . . ?
C1 N2 C15 118.86(17) . . ?
C1 N2 C5 120.66(17) . . ?
C5 N2 C15 120.48(16) . . ?
C12 N1 C13 105.13(15) . . ?
C11 C6 C5 120.94(18) . . ?
C7 C6 C11 118.43(18) . . ?
C7 C6 C5 120.62(18) . . ?
N2 C15 C12 121.18(17) . . ?
N2 C15 C14 131.47(17) . . ?
C14 C15 C12 107.26(16) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.15(19) . . ?
C8 C7 H7 119.4 . . ?
N2 C1 H1 119.3 . . ?
C2 C1 N2 121.4(2) . . ?
C2 C1 H1 119.3 . . ?
N2 C5 C6 119.32(17) . . ?
N2 C5 C4 117.05(18) . . ?
C4 C5 C6 123.63(19) . . ?
N1 C12 C11 128.95(16) . . ?
N1 C12 C15 110.60(17) . . ?
C15 C12 C11 120.42(16) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.07(19) . . ?
C9 C8 H8 120.0 . . ?
C15 C14 H14 127.6 . . ?
C15 C14 C13 104.80(16) . . ?
C13 C14 H14 127.6 . . ?
C11 C10 H10 119.9 . . ?
C9 C10 C11 120.27(18) . . ?
C9 C10 H10 119.9 . . ?
C5 C4 H4 119.0 . . ?
C3 C4 C5 122.1(2) . . ?
C3 C4 H4 119.0 . . ?
C21 C16 C13 120.36(18) . . ?
C17 C16 C21 118.14(19) . . ?
C17 C16 C13 121.49(18) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.56(19) . . ?
C10 C9 H9 119.7 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.8(2) . . ?
C20 C21 H21 119.6 . . ?
N1 C13 C14 112.20(16) . . ?
N1 C13 C16 121.29(16) . . ?
C14 C13 C16 126.47(17) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.3(2) . . ?
C3 C2 H2 120.3 . . ?
C20 C19 H19 120.4 . . ?
C20 C19 C18 119.2(2) . . ?
C18 C19 H19 120.4 . . ?
C21 C20 H20 119.8 . . ?
C19 C20 C21 120.4(2) . . ?
C19 C20 H20 119.8 . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.1(2) . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C5A N2A C15A 120.20(16) . . ?
C1A N2A C5A 120.79(18) . . ?
C1A N2A C15A 119.01(18) . . ?
C12A N1A C13A 104.88(15) . . ?
C11A C6A C5A 121.08(18) . . ?
C7A C6A C5A 120.75(18) . . ?
C7A C6A C11A 118.17(17) . . ?
N1A C12A C11A 128.74(16) . . ?
N1A C12A C15A 110.55(17) . . ?
C15A C12A C11A 120.68(18) . . ?
N2A C5A C6A 119.36(17) . . ?
N2A C5A C4A 117.11(18) . . ?
C4A C5A C6A 123.5(2) . . ?
C6A C11A C12A 117.53(17) . . ?
C10A C11A C6A 119.52(18) . . ?
C10A C11A C12A 122.93(17) . . ?
C11A C10A H10A 119.8 . . ?
C9A C10A C11A 120.49(18) . . ?
C9A C10A H10A 119.8 . . ?
N2A C15A C12A 121.06(18) . . ?
C14A C15A N2A 131.18(18) . . ?
C14A C15A C12A 107.71(17) . . ?
C10A C9A H9A 119.8 . . ?
C10A C9A C8A 120.35(18) . . ?
C8A C9A H9A 119.8 . . ?
C9A C8A H8A 119.9 . . ?
C7A C8A C9A 120.24(19) . . ?
C7A C8A H8A 119.9 . . ?
C6A C7A H7A 119.4 . . ?
C8A C7A C6A 121.21(19) . . ?
C8A C7A H7A 119.4 . . ?
N1A C13A C14A 112.41(17) . . ?
N1A C13A C16A 120.73(17) . . ?
C14A C13A C16A 126.83(18) . . ?
C5A C4A H4A 119.0 . . ?
C3A C4A C5A 122.0(2) . . ?
C3A C4A H4A 119.0 . . ?
C15A C14A C13A 104.45(17) . . ?
C15A C14A H14A 127.8 . . ?
C13A C14A H14A 127.8 . . ?
N2A C1A H1A 119.2 . . ?
C2A C1A N2A 121.5(2) . . ?
C2A C1A H1A 119.2 . . ?
C21A C16A C13A 121.29(18) . . ?
C21A C16A C17A 118.2(2) . . ?
C17A C16A C13A 120.53(19) . . ?
C1A C2A H2A 120.2 . . ?
C1A C2A C3A 119.5(2) . . ?
C3A C2A H2A 120.2 . . ?
C16A C21A H21A 119.5 . . ?
C16A C21A C20A 121.1(2) . . ?
C20A C21A H21A 119.5 . . ?
C21A C20A H20A 119.7 . . ?
C19A C20A C21A 120.6(2) . . ?
C19A C20A H20A 119.7 . . ?
C4A C3A C2A 119.1(2) . . ?
C4A C3A H3A 120.4 . . ?
C2A C3A H3A 120.4 . . ?
C16A C17A H17A 119.8 . . ?
C18A C17A C16A 120.4(2) . . ?
C18A C17A H17A 119.8 . . ?
C20A C19A H19A 120.5 . . ?
C20A C19A C18A 119.0(2) . . ?
C18A C19A H19A 120.5 . . ?
C17A C18A C19A 120.8(2) . . ?
C17A C18A H18A 119.6 . . ?
C19A C18A H18A 119.6 . . ?
H1AA O1A H1AB 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
C11 C6 C7 C8 -0.5(3) . . . . ?
C11 C6 C5 N2 2.2(3) . . . . ?
C11 C6 C5 C4 -178.23(18) . . . . ?
C11 C10 C9 C8 -0.7(3) . . . . ?
N2 C15 C12 C11 1.6(3) . . . . ?
N2 C15 C12 N1 -176.84(16) . . . . ?
N2 C15 C14 C13 176.12(19) . . . . ?
N2 C1 C2 C3 1.4(3) . . . . ?
N2 C5 C4 C3 2.6(3) . . . . ?
C6 C11 C12 N1 175.23(17) . . . . ?
C6 C11 C12 C15 -2.9(3) . . . . ?
C6 C11 C10 C9 0.2(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C6 C5 C4 C3 -177.03(19) . . . . ?
C15 N2 C1 C2 -178.74(18) . . . . ?
C15 N2 C5 C6 -3.6(3) . . . . ?
C15 N2 C5 C4 176.81(16) . . . . ?
C15 C14 C13 N1 0.5(2) . . . . ?
C15 C14 C13 C16 -177.26(18) . . . . ?
C7 C6 C5 N2 -178.58(17) . . . . ?
C7 C6 C5 C4 1.0(3) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C1 N2 C15 C12 -178.53(17) . . . . ?
C1 N2 C15 C14 5.4(3) . . . . ?
C1 N2 C5 C6 176.70(16) . . . . ?
C1 N2 C5 C4 -2.9(3) . . . . ?
C1 C2 C3 C4 -1.8(3) . . . . ?
C5 N2 C15 C12 1.7(3) . . . . ?
C5 N2 C15 C14 -174.35(19) . . . . ?
C5 N2 C1 C2 1.0(3) . . . . ?
C5 C6 C7 C8 -179.76(18) . . . . ?
C5 C4 C3 C2 -0.3(3) . . . . ?
C12 C11 C6 C7 -178.22(17) . . . . ?
C12 C11 C6 C5 1.1(3) . . . . ?
C12 C11 C10 C9 178.71(17) . . . . ?
C12 N1 C13 C14 -0.5(2) . . . . ?
C12 N1 C13 C16 177.44(16) . . . . ?
C12 C15 C14 C13 -0.4(2) . . . . ?
C14 C15 C12 C11 178.54(16) . . . . ?
C14 C15 C12 N1 0.1(2) . . . . ?
C10 C11 C6 C7 0.4(3) . . . . ?
C10 C11 C6 C5 179.68(17) . . . . ?
C10 C11 C12 N1 -3.3(3) . . . . ?
C10 C11 C12 C15 178.51(17) . . . . ?
C16 C21 C20 C19 -0.2(3) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C21 C16 C13 N1 167.03(17) . . . . ?
C21 C16 C13 C14 -15.3(3) . . . . ?
C21 C16 C17 C18 1.3(3) . . . . ?
C13 N1 C12 C11 -178.04(18) . . . . ?
C13 N1 C12 C15 0.2(2) . . . . ?
C13 C16 C21 C20 178.43(18) . . . . ?
C13 C16 C17 C18 -178.04(18) . . . . ?
C20 C19 C18 C17 -0.5(3) . . . . ?
C17 C16 C21 C20 -0.9(3) . . . . ?
C17 C16 C13 N1 -13.6(3) . . . . ?
C17 C16 C13 C14 164.01(19) . . . . ?
C18 C19 C20 C21 0.9(3) . . . . ?
N2A C5A C4A C3A 2.1(3) . . . . ?
N2A C15A C14A C13A 176.86(19) . . . . ?
N2A C1A C2A C3A 1.1(3) . . . . ?
N1A C12A C11A C6A 174.89(17) . . . . ?
N1A C12A C11A C10A -3.6(3) . . . . ?
N1A C12A C15A N2A -177.39(16) . . . . ?
N1A C12A C15A C14A 0.1(2) . . . . ?
N1A C13A C14A C15A 0.4(2) . . . . ?
N1A C13A C16A C21A -12.9(3) . . . . ?
N1A C13A C16A C17A 167.85(17) . . . . ?
C6A C5A C4A C3A -177.37(19) . . . . ?
C6A C11A C10A C9A -0.7(3) . . . . ?
C12A N1A C13A C14A -0.3(2) . . . . ?
C12A N1A C13A C16A 177.95(16) . . . . ?
C12A C11A C10A C9A 177.81(18) . . . . ?
C12A C15A C14A C13A -0.3(2) . . . . ?
C5A N2A C15A C12A 1.9(3) . . . . ?
C5A N2A C15A C14A -174.93(19) . . . . ?
C5A N2A C1A C2A 0.7(3) . . . . ?
C5A C6A C11A C12A 2.5(3) . . . . ?
C5A C6A C11A C10A -178.92(17) . . . . ?
C5A C6A C7A C8A 179.16(18) . . . . ?
C5A C4A C3A C2A -0.4(3) . . . . ?
C11A C6A C5A N2A 0.0(3) . . . . ?
C11A C6A C5A C4A 179.43(18) . . . . ?
C11A C6A C7A C8A -1.3(3) . . . . ?
C11A C12A C15A N2A 0.8(3) . . . . ?
C11A C12A C15A C14A 178.24(17) . . . . ?
C11A C10A C9A C8A -0.5(3) . . . . ?
C10A C9A C8A C7A 0.8(3) . . . . ?
C15A N2A C5A C6A -2.2(3) . . . . ?
C15A N2A C5A C4A 178.31(17) . . . . ?
C15A N2A C1A C2A -179.82(18) . . . . ?
C15A C12A C11A C6A -2.9(3) . . . . ?
C15A C12A C11A C10A 178.59(17) . . . . ?
C9A C8A C7A C6A 0.2(3) . . . . ?
C7A C6A C5A N2A 179.51(17) . . . . ?
C7A C6A C5A C4A -1.1(3) . . . . ?
C7A C6A C11A C12A -177.01(17) . . . . ?
C7A C6A C11A C10A 1.6(3) . . . . ?
C13A N1A C12A C11A -177.83(18) . . . . ?
C13A N1A C12A C15A 0.1(2) . . . . ?
C13A C16A C21A C20A -177.46(19) . . . . ?
C13A C16A C17A C18A 177.99(18) . . . . ?
C14A C13A C16A C21A 165.13(19) . . . . ?
C14A C13A C16A C17A -14.2(3) . . . . ?
C1A N2A C5A C6A 177.23(17) . . . . ?
C1A N2A C5A C4A -2.2(3) . . . . ?
C1A N2A C15A C12A -177.59(17) . . . . ?
C1A N2A C15A C14A 5.6(3) . . . . ?
C1A C2A C3A C4A -1.2(3) . . . . ?
C16A C13A C14A C15A -177.77(18) . . . . ?
C16A C21A C20A C19A -0.8(3) . . . . ?
C16A C17A C18A C19A -0.3(3) . . . . ?
C21A C16A C17A C18A -1.3(3) . . . . ?
C21A C20A C19A C18A -0.8(3) . . . . ?
C20A C19A C18A C17A 1.4(3) . . . . ?
C17A C16A C21A C20A 1.8(3) . . . . ?

####################################################################### 
# 
# 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_734
_database_code_depnum_ccdc_archive 'CCDC 1412486'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
_audit_creation_date             2015-07-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C27 H18 N2), 2(H2 O)'
_chemical_formula_sum            'C54 H40 N4 O2'
_chemical_formula_weight         776.90
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H15 N5'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   16.6795(12)
_cell_length_b                   8.7264(8)
_cell_length_c                   26.906(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.297(7)
_cell_angle_gamma                90
_cell_volume                     3840.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1687
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.0840
_cell_measurement_theta_min      5.3820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1615
_diffrn_reflns_av_unetI/netI     0.1578
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            30214
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.996
_diffrn_reflns_theta_min         3.350
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -106.00  -36.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  178.0000   90.0000 70

#__ type_ start__ end____ width___ exp.time_
  2 omega -117.00  -11.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -77.0000   90.0000 106

#__ type_ start__ end____ width___ exp.time_
  3 omega   72.00   98.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega    1.00   45.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000  -60.0000 44

#__ type_ start__ end____ width___ exp.time_
  5 omega   83.00  109.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   48.00   74.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  121.00  165.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
  8 omega   77.00  103.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   35.00   90.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 55

#__ type_ start__ end____ width___ exp.time_
 10 omega   44.00   73.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
 11 omega   85.00  138.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega  110.00  136.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   98.0000  176.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega  144.00  178.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   98.0000  176.0000 34

#__ type_ start__ end____ width___ exp.time_
 14 omega   86.00  178.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 92

#__ type_ start__ end____ width___ exp.time_
 15 omega   35.00   99.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 64

#__ type_ start__ end____ width___ exp.time_
 16 omega  111.00  143.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   90.0000 32

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00   97.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
 18 omega   29.00   55.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   42.00   79.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
 20 omega   39.00   98.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 59

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   62.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega   70.00   96.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   30.00   97.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 67

#__ type_ start__ end____ width___ exp.time_
 24 omega   64.00   98.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
 25 omega  142.00  167.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 26 omega   88.00  127.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -180.0000 39

#__ type_ start__ end____ width___ exp.time_
 27 omega  104.00  129.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 28 omega   73.00   98.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -115.0000  171.0000 25

#__ type_ start__ end____ width___ exp.time_
 29 omega   37.00   62.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 30 omega    8.00   34.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   19.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega -104.00  -14.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -77.0000    0.0000 90

#__ type_ start__ end____ width___ exp.time_
 32 omega  -85.00  -51.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   19.0000 -120.0000 34

#__ type_ start__ end____ width___ exp.time_
 33 omega  102.00  128.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   48.00   76.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
 35 omega   63.00  109.00   1.0000   17.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -180.0000 46
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0437318000
_diffrn_orient_matrix_UB_12      -0.0911189000
_diffrn_orient_matrix_UB_13      0.0359088000
_diffrn_orient_matrix_UB_21      -0.0547146000
_diffrn_orient_matrix_UB_22      0.1396263000
_diffrn_orient_matrix_UB_23      0.0043288000
_diffrn_orient_matrix_UB_31      -0.0628876000
_diffrn_orient_matrix_UB_32      -0.0582356000
_diffrn_orient_matrix_UB_33      -0.0458505000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2956
_reflns_number_total             7285
_reflns_odcompleteness_completeness 94.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         7285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1812
_refine_ls_R_factor_gt           0.0723
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.2400
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1B,H1C), O1A(H1AA,H1AB)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13),
 C14(H14), C15(H15), C16(H16), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27), C1A(H1A), C2A(H2A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A),
 C9A(H9A), C10A(H10A), C13A(H13A), C14A(H14A), C15A(H15A), C16A(H16A),
 C20A(H20A), C23A(H23A), C24A(H24A), C25A(H25A), C26A(H26A), C27A(H27A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2628(2) 0.3210(5) 0.77679(15) 0.0258(9) Uani 1 1 d . . . . .
N2 N 0.3085(2) 0.3018(5) 0.65164(15) 0.0268(9) Uani 1 1 d . . . . .
C1 C 0.2942(3) 0.4025(6) 0.82032(18) 0.0298(11) Uani 1 1 d . . . . .
H1 H 0.3360 0.4730 0.8201 0.036 Uiso 1 1 calc R . . . .
C2 C 0.2646(3) 0.3809(6) 0.86368(17) 0.0274(11) Uani 1 1 d . . . . .
H2 H 0.2850 0.4388 0.8924 0.033 Uiso 1 1 calc R . . . .
C3 C 0.2029(3) 0.2705(6) 0.86511(17) 0.0271(10) Uani 1 1 d . . . . .
C4 C 0.1731(3) 0.2358(7) 0.91232(17) 0.0290(11) Uani 1 1 d . . . . .
C5 C 0.1519(4) 0.0861(7) 0.92209(19) 0.0370(13) Uani 1 1 d . . . . .
H5 H 0.1564 0.0085 0.8991 0.044 Uiso 1 1 calc R . . . .
C6 C 0.1239(4) 0.0528(8) 0.9667(2) 0.0448(15) Uani 1 1 d . . . . .
H6 H 0.1104 -0.0474 0.9736 0.054 Uiso 1 1 calc R . . . .
C7 C 0.1161(4) 0.1689(7) 1.0006(2) 0.0418(14) Uani 1 1 d . . . . .
H7 H 0.0963 0.1468 1.0298 0.050 Uiso 1 1 calc R . . . .
C8 C 0.1378(3) 0.3181(7) 0.99099(19) 0.0334(12) Uani 1 1 d . . . . .
H8 H 0.1324 0.3958 1.0138 0.040 Uiso 1 1 calc R . . . .
C9 C 0.1674(3) 0.3514(6) 0.94753(18) 0.0296(11) Uani 1 1 d . . . . .
H9 H 0.1835 0.4508 0.9418 0.036 Uiso 1 1 calc R . . . .
C10 C 0.1709(3) 0.1951(6) 0.82101(18) 0.0270(11) Uani 1 1 d . . . . .
H10 H 0.1290 0.1249 0.8212 0.032 Uiso 1 1 calc R . . . .
C11 C 0.1987(3) 0.2192(6) 0.77521(18) 0.0250(10) Uani 1 1 d . . . . .
C12 C 0.1643(3) 0.1424(6) 0.72867(18) 0.0262(10) Uani 1 1 d . . . . .
C13 C 0.0961(3) 0.0415(6) 0.72589(18) 0.0286(11) Uani 1 1 d . . . . .
H13 H 0.0750 0.0229 0.7548 0.034 Uiso 1 1 calc R . . . .
C14 C 0.0615(3) -0.0279(7) 0.68137(19) 0.0317(12) Uani 1 1 d . . . . .
H14 H 0.0172 -0.0932 0.6802 0.038 Uiso 1 1 calc R . . . .
C15 C 0.0931(3) -0.0008(7) 0.63708(18) 0.0327(12) Uani 1 1 d . . . . .
H15 H 0.0687 -0.0474 0.6068 0.039 Uiso 1 1 calc R . . . .
C16 C 0.1590(3) 0.0933(6) 0.63840(18) 0.0292(11) Uani 1 1 d . . . . .
H16 H 0.1798 0.1087 0.6092 0.035 Uiso 1 1 calc R . . . .
C17 C 0.1955(3) 0.1672(6) 0.68378(18) 0.0259(10) Uani 1 1 d . . . . .
C18 C 0.2643(3) 0.2667(6) 0.68738(17) 0.0260(10) Uani 1 1 d . . . . .
C19 C 0.2964(3) 0.3434(6) 0.73336(17) 0.0274(11) Uani 1 1 d . . . . .
C20 C 0.3638(3) 0.4312(6) 0.72561(18) 0.0296(11) Uani 1 1 d . . . . .
H20 H 0.3975 0.4944 0.7486 0.036 Uiso 1 1 calc R . . . .
C21 C 0.3681(3) 0.4005(6) 0.67481(19) 0.0299(11) Uani 1 1 d . . . . .
C22 C 0.4277(3) 0.4636(7) 0.64682(19) 0.0310(12) Uani 1 1 d . . . . .
C23 C 0.4377(3) 0.3963(7) 0.6016(2) 0.0340(12) Uani 1 1 d . . . . .
H23 H 0.4070 0.3104 0.5896 0.041 Uiso 1 1 calc R . . . .
C24 C 0.4938(3) 0.4567(7) 0.5738(2) 0.0378(13) Uani 1 1 d . . . . .
H24 H 0.5001 0.4106 0.5437 0.045 Uiso 1 1 calc R . . . .
C25 C 0.5396(3) 0.5856(7) 0.5918(2) 0.0415(14) Uani 1 1 d . . . . .
H25 H 0.5765 0.6266 0.5736 0.050 Uiso 1 1 calc R . . . .
C26 C 0.5296(3) 0.6526(7) 0.6369(2) 0.0408(14) Uani 1 1 d . . . . .
H26 H 0.5600 0.7391 0.6487 0.049 Uiso 1 1 calc R . . . .
C27 C 0.4747(3) 0.5925(7) 0.6650(2) 0.0341(12) Uani 1 1 d . . . . .
H27 H 0.4694 0.6377 0.6954 0.041 Uiso 1 1 calc R . . . .
N1A N 0.2389(2) 0.2465(5) 0.21946(14) 0.0259(9) Uani 1 1 d . . . . .
N2A N 0.1944(2) 0.2301(5) 0.34474(15) 0.0272(9) Uani 1 1 d . . . . .
C1A C 0.2076(3) 0.3238(6) 0.17569(17) 0.0275(11) Uani 1 1 d . . . . .
H1A H 0.1651 0.3928 0.1757 0.033 Uiso 1 1 calc R . . . .
C2A C 0.2363(3) 0.3037(6) 0.13197(18) 0.0303(11) Uani 1 1 d . . . . .
H2A H 0.2137 0.3589 0.1030 0.036 Uiso 1 1 calc R . . . .
C3A C 0.3006(3) 0.1987(6) 0.13075(17) 0.0270(11) Uani 1 1 d . . . . .
C4A C 0.3320(3) 0.1645(6) 0.08427(17) 0.0265(11) Uani 1 1 d . . . . .
C5A C 0.3617(4) 0.0204(7) 0.07738(18) 0.0378(13) Uani 1 1 d . . . . .
H5A H 0.3598 -0.0560 0.1012 0.045 Uiso 1 1 calc R . . . .
C6A C 0.3947(4) -0.0110(7) 0.03479(19) 0.0392(14) Uani 1 1 d . . . . .
H6A H 0.4166 -0.1072 0.0307 0.047 Uiso 1 1 calc R . . . .
C7A C 0.3947(3) 0.1020(8) -0.00180(19) 0.0421(16) Uani 1 1 d . . . . .
H7A H 0.4152 0.0802 -0.0308 0.051 Uiso 1 1 calc R . . . .
C8A C 0.3646(3) 0.2458(8) 0.00490(18) 0.0385(14) Uani 1 1 d . . . . .
H8A H 0.3659 0.3217 -0.0192 0.046 Uiso 1 1 calc R . . . .
C9A C 0.3321(3) 0.2779(7) 0.04790(17) 0.0321(12) Uani 1 1 d . . . . .
H9A H 0.3108 0.3744 0.0522 0.038 Uiso 1 1 calc R . . . .
C10A C 0.3328(3) 0.1243(6) 0.17575(17) 0.0266(11) Uani 1 1 d . . . . .
H10A H 0.3758 0.0564 0.1761 0.032 Uiso 1 1 calc R . . . .
C11A C 0.3036(3) 0.1460(6) 0.22117(17) 0.0239(10) Uani 1 1 d . . . . .
C12A C 0.3383(3) 0.0689(6) 0.26786(17) 0.0223(9) Uani 1 1 d . . . . .
C13A C 0.4042(3) -0.0358(6) 0.27014(17) 0.0277(11) Uani 1 1 d . . . . .
H13A H 0.4249 -0.0555 0.2411 0.033 Uiso 1 1 calc R . . . .
C14A C 0.4376(3) -0.1080(7) 0.31464(18) 0.0304(12) Uani 1 1 d . . . . .
H14A H 0.4818 -0.1737 0.3157 0.036 Uiso 1 1 calc R . . . .
C15A C 0.4055(3) -0.0837(6) 0.35886(18) 0.0287(11) Uani 1 1 d . . . . .
H15A H 0.4280 -0.1343 0.3888 0.034 Uiso 1 1 calc R . . . .
C16A C 0.3409(3) 0.0151(6) 0.35745(17) 0.0276(11) Uani 1 1 d . . . . .
H16A H 0.3200 0.0311 0.3866 0.033 Uiso 1 1 calc R . . . .
C17A C 0.3060(3) 0.0921(6) 0.31275(17) 0.0227(10) Uani 1 1 d . . . . .
C18A C 0.2380(3) 0.1928(6) 0.30856(17) 0.0231(10) Uani 1 1 d . . . . .
C19A C 0.2051(3) 0.2693(6) 0.26238(17) 0.0256(10) Uani 1 1 d . . . . .
C20A C 0.1376(3) 0.3550(6) 0.26996(18) 0.0272(10) Uani 1 1 d . . . . .
H20A H 0.1031 0.4159 0.2467 0.033 Uiso 1 1 calc R . . . .
C21A C 0.1339(3) 0.3274(6) 0.32111(18) 0.0251(10) Uani 1 1 d . . . . .
C22A C 0.0745(3) 0.3945(6) 0.34861(18) 0.0277(11) Uani 1 1 d . . . . .
C23A C 0.0617(3) 0.3298(7) 0.39410(19) 0.0318(12) Uani 1 1 d . . . . .
H23A H 0.0899 0.2414 0.4064 0.038 Uiso 1 1 calc R . . . .
C24A C 0.0075(3) 0.3950(7) 0.4213(2) 0.0369(13) Uani 1 1 d . . . . .
H24A H 0.0014 0.3521 0.4520 0.044 Uiso 1 1 calc R . . . .
C25A C -0.0376(3) 0.5242(7) 0.4028(2) 0.0353(12) Uani 1 1 d . . . . .
H25A H -0.0752 0.5665 0.4203 0.042 Uiso 1 1 calc R . . . .
C26A C -0.0252(3) 0.5882(7) 0.3578(2) 0.0350(12) Uani 1 1 d . . . . .
H26A H -0.0539 0.6761 0.3455 0.042 Uiso 1 1 calc R . . . .
C27A C 0.0295(3) 0.5234(6) 0.33042(18) 0.0305(11) Uani 1 1 d . . . . .
H27A H 0.0358 0.5671 0.2999 0.037 Uiso 1 1 calc R . . . .
O1 O 0.2150(2) 0.3540(6) 0.54833(15) 0.0454(11) Uani 1 1 d . . . . .
H1B H 0.2297 0.2920 0.5275 0.068 Uiso 1 1 d G . . . .
H1C H 0.2469 0.3456 0.5770 0.068 Uiso 1 1 d G . . . .
O1A O 0.2746(3) 0.2680(5) 0.45236(15) 0.0471(11) Uani 1 1 d . . . . .
H1AA H 0.2607 0.2599 0.4204 0.071 Uiso 1 1 d G . . . .
H1AB H 0.2892 0.3597 0.4601 0.071 Uiso 1 1 d G . . . .


_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 C1 1.383(6) . ?
N1 C11 1.384(6) . ?
N1 C19 1.405(6) . ?
N2 C18 1.356(6) . ?
N2 C21 1.370(7) . ?
C1 H1 0.9300 . ?
C1 C2 1.366(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.415(7) . ?
C3 C4 1.483(7) . ?
C3 C10 1.370(7) . ?
C4 C5 1.392(8) . ?
C4 C9 1.400(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.401(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.389(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.415(7) . ?
C11 C12 1.437(7) . ?
C12 C13 1.429(7) . ?
C12 C17 1.422(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.365(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.413(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.367(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.409(7) . ?
C17 C18 1.427(7) . ?
C18 C19 1.416(7) . ?
C19 C20 1.411(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.408(7) . ?
C21 C22 1.467(7) . ?
C22 C23 1.390(7) . ?
C22 C27 1.403(8) . ?
C23 H23 0.9300 . ?
C23 C24 1.409(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.392(9) . ?
C25 H25 0.9300 . ?
C25 C26 1.388(9) . ?
C26 H26 0.9300 . ?
C26 C27 1.397(7) . ?
C27 H27 0.9300 . ?
N1A C1A 1.369(6) . ?
N1A C11A 1.385(6) . ?
N1A C19A 1.395(6) . ?
N2A C18A 1.363(6) . ?
N2A C21A 1.376(6) . ?
C1A H1A 0.9300 . ?
C1A C2A 1.366(7) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.416(7) . ?
C3A C4A 1.477(6) . ?
C3A C10A 1.386(7) . ?
C4A C5A 1.378(8) . ?
C4A C9A 1.392(7) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.392(7) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.394(8) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.376(9) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.399(7) . ?
C9A H9A 0.9300 . ?
C10A H10A 0.9300 . ?
C10A C11A 1.414(6) . ?
C11A C12A 1.442(6) . ?
C12A C13A 1.422(7) . ?
C12A C17A 1.430(6) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.371(7) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.413(7) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.375(7) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.401(7) . ?
C17A C18A 1.422(7) . ?
C18A C19A 1.422(6) . ?
C19A C20A 1.399(7) . ?
C20A H20A 0.9300 . ?
C20A C21A 1.410(7) . ?
C21A C22A 1.469(6) . ?
C22A C23A 1.402(7) . ?
C22A C27A 1.387(7) . ?
C23A H23A 0.9300 . ?
C23A C24A 1.390(7) . ?
C24A H24A 0.9300 . ?
C24A C25A 1.391(8) . ?
C25A H25A 0.9300 . ?
C25A C26A 1.387(8) . ?
C26A H26A 0.9300 . ?
C26A C27A 1.399(7) . ?
C27A H27A 0.9300 . ?
O1 H1B 0.8504 . ?
O1 H1C 0.8499 . ?
O1A H1AA 0.8497 . ?
O1A H1AB 0.8499 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 121.2(4) . . ?
C1 N1 C19 119.1(4) . . ?
C11 N1 C19 119.7(4) . . ?
C18 N2 C21 105.5(4) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 N1 120.7(5) . . ?
C2 C1 H1 119.6 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.3(5) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 122.0(5) . . ?
C10 C3 C2 117.7(4) . . ?
C10 C3 C4 120.3(5) . . ?
C5 C4 C3 119.6(5) . . ?
C5 C4 C9 119.7(5) . . ?
C9 C4 C3 120.8(5) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(5) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.1(6) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.1(5) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.1(5) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 119.9 . . ?
C8 C9 C4 120.2(5) . . ?
C8 C9 H9 119.9 . . ?
C3 C10 H10 118.5 . . ?
C3 C10 C11 122.9(5) . . ?
C11 C10 H10 118.5 . . ?
N1 C11 C10 116.9(4) . . ?
N1 C11 C12 120.0(4) . . ?
C10 C11 C12 123.1(5) . . ?
C13 C12 C11 120.7(4) . . ?
C17 C12 C11 121.3(5) . . ?
C17 C12 C13 118.0(5) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(4) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(5) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(5) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(4) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C18 117.3(4) . . ?
C16 C17 C12 119.9(5) . . ?
C16 C17 C18 122.9(4) . . ?
N2 C18 C17 129.1(5) . . ?
N2 C18 C19 110.4(5) . . ?
C19 C18 C17 120.5(4) . . ?
N1 C19 C18 121.1(5) . . ?
N1 C19 C20 131.2(5) . . ?
C20 C19 C18 107.7(4) . . ?
C19 C20 H20 128.2 . . ?
C21 C20 C19 103.5(4) . . ?
C21 C20 H20 128.2 . . ?
N2 C21 C20 113.0(4) . . ?
N2 C21 C22 120.5(5) . . ?
C20 C21 C22 126.5(5) . . ?
C23 C22 C21 120.0(5) . . ?
C23 C22 C27 119.2(5) . . ?
C27 C22 C21 120.7(5) . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.8(6) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 120.2 . . ?
C25 C24 C23 119.6(6) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.5(5) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 119.4 . . ?
C25 C26 C27 121.2(6) . . ?
C27 C26 H26 119.4 . . ?
C22 C27 H27 120.2 . . ?
C26 C27 C22 119.6(5) . . ?
C26 C27 H27 120.2 . . ?
C1A N1A C11A 120.3(4) . . ?
C1A N1A C19A 119.6(4) . . ?
C11A N1A C19A 120.1(4) . . ?
C18A N2A C21A 105.2(4) . . ?
N1A C1A H1A 118.7 . . ?
C2A C1A N1A 122.6(5) . . ?
C2A C1A H1A 118.7 . . ?
C1A C2A H2A 120.1 . . ?
C1A C2A C3A 119.9(5) . . ?
C3A C2A H2A 120.1 . . ?
C2A C3A C4A 123.1(4) . . ?
C10A C3A C2A 116.6(4) . . ?
C10A C3A C4A 120.3(5) . . ?
C5A C4A C3A 119.7(5) . . ?
C5A C4A C9A 120.3(5) . . ?
C9A C4A C3A 120.1(5) . . ?
C4A C5A H5A 120.0 . . ?
C4A C5A C6A 120.1(5) . . ?
C6A C5A H5A 120.0 . . ?
C5A C6A H6A 120.1 . . ?
C5A C6A C7A 119.8(6) . . ?
C7A C6A H6A 120.1 . . ?
C6A C7A H7A 119.9 . . ?
C8A C7A C6A 120.1(5) . . ?
C8A C7A H7A 119.9 . . ?
C7A C8A H8A 119.9 . . ?
C7A C8A C9A 120.1(5) . . ?
C9A C8A H8A 119.9 . . ?
C4A C9A C8A 119.6(6) . . ?
C4A C9A H9A 120.2 . . ?
C8A C9A H9A 120.2 . . ?
C3A C10A H10A 118.2 . . ?
C3A C10A C11A 123.6(5) . . ?
C11A C10A H10A 118.2 . . ?
N1A C11A C10A 117.0(4) . . ?
N1A C11A C12A 120.1(4) . . ?
C10A C11A C12A 122.9(5) . . ?
C13A C12A C11A 120.8(4) . . ?
C13A C12A C17A 118.1(4) . . ?
C17A C12A C11A 121.1(4) . . ?
C12A C13A H13A 119.6 . . ?
C14A C13A C12A 120.8(4) . . ?
C14A C13A H13A 119.6 . . ?
C13A C14A H14A 119.6 . . ?
C13A C14A C15A 120.7(5) . . ?
C15A C14A H14A 119.6 . . ?
C14A C15A H15A 120.2 . . ?
C16A C15A C14A 119.7(5) . . ?
C16A C15A H15A 120.2 . . ?
C15A C16A H16A 119.5 . . ?
C15A C16A C17A 121.1(4) . . ?
C17A C16A H16A 119.5 . . ?
C16A C17A C12A 119.7(5) . . ?
C16A C17A C18A 123.7(4) . . ?
C18A C17A C12A 116.6(4) . . ?
N2A C18A C17A 128.3(4) . . ?
N2A C18A C19A 110.1(4) . . ?
C17A C18A C19A 121.6(4) . . ?
N1A C19A C18A 120.4(4) . . ?
N1A C19A C20A 131.6(5) . . ?
C20A C19A C18A 107.9(4) . . ?
C19A C20A H20A 128.0 . . ?
C19A C20A C21A 104.0(4) . . ?
C21A C20A H20A 128.0 . . ?
N2A C21A C20A 112.8(4) . . ?
N2A C21A C22A 121.3(4) . . ?
C20A C21A C22A 125.9(5) . . ?
C23A C22A C21A 120.9(5) . . ?
C27A C22A C21A 121.1(5) . . ?
C27A C22A C23A 118.1(5) . . ?
C22A C23A H23A 119.3 . . ?
C24A C23A C22A 121.4(5) . . ?
C24A C23A H23A 119.3 . . ?
C23A C24A H24A 119.8 . . ?
C23A C24A C25A 120.4(5) . . ?
C25A C24A H24A 119.8 . . ?
C24A C25A H25A 120.8 . . ?
C26A C25A C24A 118.4(5) . . ?
C26A C25A H25A 120.8 . . ?
C25A C26A H26A 119.3 . . ?
C25A C26A C27A 121.4(5) . . ?
C27A C26A H26A 119.3 . . ?
C22A C27A C26A 120.4(5) . . ?
C22A C27A H27A 119.8 . . ?
C26A C27A H27A 119.8 . . ?
H1B O1 H1C 109.5 . . ?
H1AA O1A H1AB 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
N1 C1 C2 C3 2.1(8) . . . . ?
N1 C11 C12 C13 -177.6(5) . . . . ?
N1 C11 C12 C17 0.9(8) . . . . ?
N1 C19 C20 C21 177.4(6) . . . . ?
N2 C18 C19 N1 -177.6(5) . . . . ?
N2 C18 C19 C20 0.3(6) . . . . ?
N2 C21 C22 C23 -16.2(8) . . . . ?
N2 C21 C22 C27 163.3(5) . . . . ?
C1 N1 C11 C10 -4.2(7) . . . . ?
C1 N1 C11 C12 176.5(5) . . . . ?
C1 N1 C19 C18 -177.7(5) . . . . ?
C1 N1 C19 C20 5.0(9) . . . . ?
C1 C2 C3 C4 175.7(5) . . . . ?
C1 C2 C3 C10 -4.2(8) . . . . ?
C2 C3 C4 C5 -143.8(5) . . . . ?
C2 C3 C4 C9 35.1(8) . . . . ?
C2 C3 C10 C11 2.2(8) . . . . ?
C3 C4 C5 C6 179.9(5) . . . . ?
C3 C4 C9 C8 178.6(5) . . . . ?
C3 C10 C11 N1 1.9(7) . . . . ?
C3 C10 C11 C12 -178.8(5) . . . . ?
C4 C3 C10 C11 -177.7(5) . . . . ?
C4 C5 C6 C7 0.9(10) . . . . ?
C5 C4 C9 C8 -2.5(8) . . . . ?
C5 C6 C7 C8 -1.4(10) . . . . ?
C6 C7 C8 C9 -0.1(9) . . . . ?
C7 C8 C9 C4 2.1(8) . . . . ?
C9 C4 C5 C6 1.0(9) . . . . ?
C10 C3 C4 C5 36.2(7) . . . . ?
C10 C3 C4 C9 -145.0(5) . . . . ?
C10 C11 C12 C13 3.1(8) . . . . ?
C10 C11 C12 C17 -178.4(5) . . . . ?
C11 N1 C1 C2 2.3(8) . . . . ?
C11 N1 C19 C18 1.8(8) . . . . ?
C11 N1 C19 C20 -175.6(5) . . . . ?
C11 C12 C13 C14 177.9(5) . . . . ?
C11 C12 C17 C16 -178.3(5) . . . . ?
C11 C12 C17 C18 2.3(8) . . . . ?
C12 C13 C14 C15 0.1(8) . . . . ?
C12 C17 C18 N2 175.5(5) . . . . ?
C12 C17 C18 C19 -3.5(8) . . . . ?
C13 C12 C17 C16 0.2(8) . . . . ?
C13 C12 C17 C18 -179.2(5) . . . . ?
C13 C14 C15 C16 0.9(9) . . . . ?
C14 C15 C16 C17 -1.3(9) . . . . ?
C15 C16 C17 C12 0.7(8) . . . . ?
C15 C16 C17 C18 -179.9(5) . . . . ?
C16 C17 C18 N2 -3.8(9) . . . . ?
C16 C17 C18 C19 177.2(5) . . . . ?
C17 C12 C13 C14 -0.6(8) . . . . ?
C17 C18 C19 N1 1.5(8) . . . . ?
C17 C18 C19 C20 179.4(5) . . . . ?
C18 N2 C21 C20 -0.1(6) . . . . ?
C18 N2 C21 C22 -179.7(5) . . . . ?
C18 C19 C20 C21 -0.3(6) . . . . ?
C19 N1 C1 C2 -178.3(5) . . . . ?
C19 N1 C11 C10 176.4(5) . . . . ?
C19 N1 C11 C12 -2.9(7) . . . . ?
C19 C20 C21 N2 0.2(6) . . . . ?
C19 C20 C21 C22 179.8(5) . . . . ?
C20 C21 C22 C23 164.2(5) . . . . ?
C20 C21 C22 C27 -16.2(9) . . . . ?
C21 N2 C18 C17 -179.2(5) . . . . ?
C21 N2 C18 C19 -0.1(6) . . . . ?
C21 C22 C23 C24 179.0(5) . . . . ?
C21 C22 C27 C26 -178.4(5) . . . . ?
C22 C23 C24 C25 -0.2(8) . . . . ?
C23 C22 C27 C26 1.1(8) . . . . ?
C23 C24 C25 C26 0.3(8) . . . . ?
C24 C25 C26 C27 0.4(9) . . . . ?
C25 C26 C27 C22 -1.1(8) . . . . ?
C27 C22 C23 C24 -0.5(8) . . . . ?
N1A C1A C2A C3A 0.4(8) . . . . ?
N1A C11A C12A C13A 179.4(5) . . . . ?
N1A C11A C12A C17A 1.0(7) . . . . ?
N1A C19A C20A C21A 178.3(6) . . . . ?
N2A C18A C19A N1A -178.8(5) . . . . ?
N2A C18A C19A C20A -1.1(6) . . . . ?
N2A C21A C22A C23A -18.8(8) . . . . ?
N2A C21A C22A C27A 161.1(5) . . . . ?
C1A N1A C11A C10A -2.3(7) . . . . ?
C1A N1A C11A C12A 177.8(5) . . . . ?
C1A N1A C19A C18A -178.5(5) . . . . ?
C1A N1A C19A C20A 4.4(9) . . . . ?
C1A C2A C3A C4A 176.6(5) . . . . ?
C1A C2A C3A C10A -1.9(8) . . . . ?
C2A C3A C4A C5A -148.1(5) . . . . ?
C2A C3A C4A C9A 32.5(8) . . . . ?
C2A C3A C10A C11A 1.4(8) . . . . ?
C3A C4A C5A C6A -177.2(5) . . . . ?
C3A C4A C9A C8A 177.8(5) . . . . ?
C3A C10A C11A N1A 0.7(8) . . . . ?
C3A C10A C11A C12A -179.4(5) . . . . ?
C4A C3A C10A C11A -177.2(5) . . . . ?
C4A C5A C6A C7A -2.4(9) . . . . ?
C5A C4A C9A C8A -1.6(8) . . . . ?
C5A C6A C7A C8A 2.0(9) . . . . ?
C6A C7A C8A C9A -1.5(9) . . . . ?
C7A C8A C9A C4A 1.3(8) . . . . ?
C9A C4A C5A C6A 2.2(8) . . . . ?
C10A C3A C4A C5A 30.4(7) . . . . ?
C10A C3A C4A C9A -149.0(5) . . . . ?
C10A C11A C12A C13A -0.6(7) . . . . ?
C10A C11A C12A C17A -178.9(5) . . . . ?
C11A N1A C1A C2A 1.8(8) . . . . ?
C11A N1A C19A C18A 1.6(7) . . . . ?
C11A N1A C19A C20A -175.5(5) . . . . ?
C11A C12A C13A C14A 179.4(5) . . . . ?
C11A C12A C17A C16A 179.8(5) . . . . ?
C11A C12A C17A C18A 0.8(7) . . . . ?
C12A C13A C14A C15A 2.0(8) . . . . ?
C12A C17A C18A N2A 177.5(5) . . . . ?
C12A C17A C18A C19A -1.5(7) . . . . ?
C13A C12A C17A C16A 1.5(7) . . . . ?
C13A C12A C17A C18A -177.5(4) . . . . ?
C13A C14A C15A C16A -0.9(8) . . . . ?
C14A C15A C16A C17A 0.2(8) . . . . ?
C15A C16A C17A C12A -0.5(8) . . . . ?
C15A C16A C17A C18A 178.5(5) . . . . ?
C16A C17A C18A N2A -1.5(8) . . . . ?
C16A C17A C18A C19A 179.6(5) . . . . ?
C17A C12A C13A C14A -2.2(8) . . . . ?
C17A C18A C19A N1A 0.3(8) . . . . ?
C17A C18A C19A C20A 178.0(5) . . . . ?
C18A N2A C21A C20A -0.3(6) . . . . ?
C18A N2A C21A C22A -179.1(5) . . . . ?
C18A C19A C20A C21A 0.9(6) . . . . ?
C19A N1A C1A C2A -178.1(5) . . . . ?
C19A N1A C11A C10A 177.7(5) . . . . ?
C19A N1A C11A C12A -2.3(7) . . . . ?
C19A C20A C21A N2A -0.4(6) . . . . ?
C19A C20A C21A C22A 178.4(5) . . . . ?
C20A C21A C22A C23A 162.5(5) . . . . ?
C20A C21A C22A C27A -17.6(8) . . . . ?
C21A N2A C18A C17A -178.2(5) . . . . ?
C21A N2A C18A C19A 0.8(6) . . . . ?
C21A C22A C23A C24A 177.9(5) . . . . ?
C21A C22A C27A C26A -178.3(5) . . . . ?
C22A C23A C24A C25A 2.2(8) . . . . ?
C23A C22A C27A C26A 1.6(8) . . . . ?
C23A C24A C25A C26A -2.0(8) . . . . ?
C24A C25A C26A C27A 1.7(8) . . . . ?
C25A C26A C27A C22A -1.5(8) . . . . ?
C27A C22A C23A C24A -2.0(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
