# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1434961'
_audit_update_record             
;
2015-11-03 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H17 F N2 O2'
_chemical_formula_weight         396.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.9284(9)
_cell_length_b                   18.6077(14)
_cell_length_c                   10.9054(8)
_cell_angle_alpha                90
_cell_angle_beta                 118.516(2)
_cell_angle_gamma                90
_cell_volume                     1948.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    0(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44308
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.121
_diffrn_reflns_theta_max         28.310
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4838
_reflns_number_gt                3519
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+0.4715P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4838
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002

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
F1 F 0.46465(11) 0.16955(6) 0.00943(13) 0.0744(4) Uani 1 1 d . . . . .
O1 O 1.00947(12) 0.24423(7) 0.18273(13) 0.0582(3) Uani 1 1 d . . . . .
O2 O 1.29188(12) 0.35469(6) 0.69174(11) 0.0499(3) Uani 1 1 d . . . . .
N1 N 1.03790(12) 0.33202(6) 0.33794(12) 0.0361(3) Uani 1 1 d . . . . .
N2 N 1.13144(12) 0.36683(6) 0.46325(12) 0.0338(3) Uani 1 1 d . . . . .
C1 C 0.66469(19) 0.56591(10) -0.21121(17) 0.0559(5) Uani 1 1 d . . . . .
H1 H 0.6410 0.5851 -0.3005 0.067 Uiso 1 1 calc R U . . .
C2 C 0.7716(2) 0.51739(11) -0.14919(19) 0.0614(5) Uani 1 1 d . . . . .
H7 H 0.8223 0.5031 -0.1957 0.074 Uiso 1 1 calc R U . . .
C3 C 0.80609(18) 0.48908(9) -0.01887(17) 0.0489(4) Uani 1 1 d . . . . .
H8 H 0.8808 0.4558 0.0234 0.059 Uiso 1 1 calc R U . . .
C4 C 0.73305(14) 0.50875(7) 0.04993(14) 0.0324(3) Uani 1 1 d . . . . .
C5 C 0.76133(14) 0.47748(8) 0.18974(14) 0.0336(3) Uani 1 1 d . . . . .
H10 H 0.7610 0.5171 0.2501 0.040 Uiso 1 1 calc R U . . .
H9 H 0.6841 0.4445 0.1743 0.040 Uiso 1 1 calc R U . . .
C6 C 0.89644(14) 0.43722(7) 0.26608(13) 0.0310(3) Uani 1 1 d . . . . .
C7 C 0.90462(14) 0.36541(7) 0.26101(13) 0.0326(3) Uani 1 1 d . . . . .
C8 C 1.07216(16) 0.26696(8) 0.30170(17) 0.0448(4) Uani 1 1 d . . . . .
C9 C 1.17367(18) 0.22589(9) 0.4208(2) 0.0606(5) Uani 1 1 d . . . . .
H4 H 1.1999 0.1794 0.4055 0.073 Uiso 1 1 calc R U . . .
C10 C 1.23018(18) 0.25149(9) 0.5493(2) 0.0565(5) Uani 1 1 d . . . . .
H2 H 1.2796 0.2196 0.6253 0.068 Uiso 1 1 calc R U . . .
C11 C 0.56955(17) 0.21850(9) 0.07095(19) 0.0487(4) Uani 1 1 d . . . . .
C12 C 0.57596(18) 0.27378(10) -0.00756(18) 0.0532(4) Uani 1 1 d . . . . .
H17 H 0.5070 0.2794 -0.1023 0.064 Uiso 1 1 calc R U . . .
C13 C 0.68592(16) 0.32169(9) 0.05461(16) 0.0458(4) Uani 1 1 d . . . . .
H3 H 0.6929 0.3602 0.0011 0.055 Uiso 1 1 calc R U . . .
C14 C 0.78577(14) 0.31450(8) 0.19315(14) 0.0352(3) Uani 1 1 d . . . . .
C15 C 1.21920(15) 0.32705(8) 0.57836(15) 0.0391(3) Uani 1 1 d . . . . .
C16 C 1.14403(14) 0.44220(7) 0.44690(13) 0.0307(3) Uani 1 1 d . . . . .
C17 C 1.02445(14) 0.47819(7) 0.34954(13) 0.0306(3) Uani 1 1 d . . . . .
C18 C 0.59216(17) 0.58648(9) -0.14339(17) 0.0470(4) Uani 1 1 d . . . . .
H6 H 0.5182 0.6202 -0.1858 0.056 Uiso 1 1 calc R U . . .
C19 C 0.62603(14) 0.55847(8) -0.01378(15) 0.0373(3) Uani 1 1 d . . . . .
H5 H 0.5755 0.5734 0.0325 0.045 Uiso 1 1 calc R U . . .
C20 C 1.03253(16) 0.55268(8) 0.33870(15) 0.0380(3) Uani 1 1 d . . . . .
H14 H 0.9518 0.5787 0.2764 0.046 Uiso 1 1 calc R U . . .
C21 C 1.15582(17) 0.58904(8) 0.41697(16) 0.0447(4) Uani 1 1 d . . . . .
H13 H 1.1592 0.6398 0.4097 0.054 Uiso 1 1 calc R U . . .
C22 C 1.27400(17) 0.55157(8) 0.50575(16) 0.0442(4) Uani 1 1 d . . . . .
H12 H 1.3597 0.5765 0.5561 0.053 Uiso 1 1 calc R U . . .
C23 C 1.26917(15) 0.47819(8) 0.52244(14) 0.0380(3) Uani 1 1 d . . . . .
H11 H 1.3506 0.4527 0.5849 0.046 Uiso 1 1 calc R U . . .
C24 C 0.77285(17) 0.25818(9) 0.26986(16) 0.0455(4) Uani 1 1 d . . . . .
H15 H 0.8393 0.2530 0.3656 0.055 Uiso 1 1 calc R U . . .
C25 C 0.66432(19) 0.20958(9) 0.20837(19) 0.0524(4) Uani 1 1 d . . . . .
H16 H 0.6559 0.1708 0.2606 0.063 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C11 1.3636(18) . ?
O1 C8 1.2177(19) . ?
O2 C15 1.2193(17) . ?
N1 C8 1.3795(19) . ?
N1 N2 1.4136(15) . ?
N1 C7 1.4300(17) . ?
N2 C15 1.3763(18) . ?
N2 C16 1.4286(17) . ?
C1 C18 1.372(3) . ?
C1 C2 1.372(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(2) . ?
C2 H7 0.9500 . ?
C3 C4 1.381(2) . ?
C3 H8 0.9500 . ?
C4 C19 1.3896(19) . ?
C4 C5 1.5196(19) . ?
C5 C6 1.5036(18) . ?
C5 H10 0.9900 . ?
C5 H9 0.9900 . ?
C6 C7 1.342(2) . ?
C6 C17 1.4666(19) . ?
C7 C14 1.4881(19) . ?
C8 C9 1.458(2) . ?
C9 C10 1.322(3) . ?
C9 H4 0.9500 . ?
C10 C15 1.459(2) . ?
C10 H2 0.9500 . ?
C11 C12 1.361(3) . ?
C11 C25 1.365(3) . ?
C12 C13 1.386(2) . ?
C12 H17 0.9500 . ?
C13 C14 1.385(2) . ?
C13 H3 0.9500 . ?
C14 C24 1.390(2) . ?
C16 C23 1.3863(19) . ?
C16 C17 1.3995(18) . ?
C17 C20 1.3976(19) . ?
C18 C19 1.381(2) . ?
C18 H6 0.9500 . ?
C19 H5 0.9500 . ?
C20 C21 1.380(2) . ?
C20 H14 0.9500 . ?
C21 C22 1.378(2) . ?
C21 H13 0.9500 . ?
C22 C23 1.382(2) . ?
C22 H12 0.9500 . ?
C23 H11 0.9500 . ?
C24 C25 1.384(2) . ?
C24 H15 0.9500 . ?
C25 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 N2 120.61(11) . . ?
C8 N1 C7 123.57(11) . . ?
N2 N1 C7 115.59(10) . . ?
C15 N2 N1 120.18(11) . . ?
C15 N2 C16 125.11(11) . . ?
N1 N2 C16 113.42(10) . . ?
C18 C1 C2 119.55(15) . . ?
C18 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C1 C2 C3 120.33(17) . . ?
C1 C2 H7 119.8 . . ?
C3 C2 H7 119.8 . . ?
C4 C3 C2 120.73(15) . . ?
C4 C3 H8 119.6 . . ?
C2 C3 H8 119.6 . . ?
C3 C4 C19 118.16(13) . . ?
C3 C4 C5 123.39(13) . . ?
C19 C4 C5 118.43(12) . . ?
C6 C5 C4 114.95(11) . . ?
C6 C5 H10 108.5 . . ?
C4 C5 H10 108.5 . . ?
C6 C5 H9 108.5 . . ?
C4 C5 H9 108.5 . . ?
H10 C5 H9 107.5 . . ?
C7 C6 C17 118.72(12) . . ?
C7 C6 C5 122.71(12) . . ?
C17 C6 C5 118.57(12) . . ?
C6 C7 N1 118.54(12) . . ?
C6 C7 C14 126.50(12) . . ?
N1 C7 C14 114.70(12) . . ?
O1 C8 N1 121.23(14) . . ?
O1 C8 C9 124.66(15) . . ?
N1 C8 C9 113.58(14) . . ?
C10 C9 C8 121.82(15) . . ?
C10 C9 H4 119.1 . . ?
C8 C9 H4 119.1 . . ?
C9 C10 C15 122.18(15) . . ?
C9 C10 H2 118.9 . . ?
C15 C10 H2 118.9 . . ?
C12 C11 F1 118.61(16) . . ?
C12 C11 C25 122.84(15) . . ?
F1 C11 C25 118.55(16) . . ?
C11 C12 C13 118.12(15) . . ?
C11 C12 H17 120.9 . . ?
C13 C12 H17 120.9 . . ?
C14 C13 C12 121.29(15) . . ?
C14 C13 H3 119.4 . . ?
C12 C13 H3 119.4 . . ?
C13 C14 C24 118.43(14) . . ?
C13 C14 C7 121.82(13) . . ?
C24 C14 C7 119.75(13) . . ?
O2 C15 N2 122.07(13) . . ?
O2 C15 C10 123.07(14) . . ?
N2 C15 C10 114.46(13) . . ?
C23 C16 C17 121.25(12) . . ?
C23 C16 N2 121.77(12) . . ?
C17 C16 N2 116.98(12) . . ?
C20 C17 C16 117.71(13) . . ?
C20 C17 C6 122.90(12) . . ?
C16 C17 C6 119.38(12) . . ?
C1 C18 C19 120.34(15) . . ?
C1 C18 H6 119.8 . . ?
C19 C18 H6 119.8 . . ?
C18 C19 C4 120.89(14) . . ?
C18 C19 H5 119.6 . . ?
C4 C19 H5 119.6 . . ?
C21 C20 C17 121.10(14) . . ?
C21 C20 H14 119.4 . . ?
C17 C20 H14 119.4 . . ?
C22 C21 C20 119.84(14) . . ?
C22 C21 H13 120.1 . . ?
C20 C21 H13 120.1 . . ?
C21 C22 C23 120.71(14) . . ?
C21 C22 H12 119.6 . . ?
C23 C22 H12 119.6 . . ?
C22 C23 C16 119.20(14) . . ?
C22 C23 H11 120.4 . . ?
C16 C23 H11 120.4 . . ?
C25 C24 C14 120.74(15) . . ?
C25 C24 H15 119.6 . . ?
C14 C24 H15 119.6 . . ?
C11 C25 C24 118.56(16) . . ?
C11 C25 H16 120.7 . . ?
C24 C25 H16 120.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 N2 C15 -31.7(2) . . . . ?
C7 N1 N2 C15 143.03(13) . . . . ?
C8 N1 N2 C16 135.97(14) . . . . ?
C7 N1 N2 C16 -49.29(16) . . . . ?
C18 C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C19 -1.1(3) . . . . ?
C2 C3 C4 C5 177.34(16) . . . . ?
C3 C4 C5 C6 14.4(2) . . . . ?
C19 C4 C5 C6 -167.17(12) . . . . ?
C4 C5 C6 C7 -97.35(16) . . . . ?
C4 C5 C6 C17 82.69(15) . . . . ?
C17 C6 C7 N1 0.33(19) . . . . ?
C5 C6 C7 N1 -179.63(12) . . . . ?
C17 C6 C7 C14 174.10(12) . . . . ?
C5 C6 C7 C14 -5.9(2) . . . . ?
C8 N1 C7 C6 -153.29(14) . . . . ?
N2 N1 C7 C6 32.15(18) . . . . ?
C8 N1 C7 C14 32.22(19) . . . . ?
N2 N1 C7 C14 -142.34(12) . . . . ?
N2 N1 C8 O1 -163.19(15) . . . . ?
C7 N1 C8 O1 22.5(2) . . . . ?
N2 N1 C8 C9 24.8(2) . . . . ?
C7 N1 C8 C9 -149.51(15) . . . . ?
O1 C8 C9 C10 -174.52(19) . . . . ?
N1 C8 C9 C10 -2.8(3) . . . . ?
C8 C9 C10 C15 -13.6(3) . . . . ?
F1 C11 C12 C13 -177.64(15) . . . . ?
C25 C11 C12 C13 1.8(3) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C12 C13 C14 C24 -0.6(2) . . . . ?
C12 C13 C14 C7 179.78(15) . . . . ?
C6 C7 C14 C13 54.4(2) . . . . ?
N1 C7 C14 C13 -131.67(15) . . . . ?
C6 C7 C14 C24 -125.27(16) . . . . ?
N1 C7 C14 C24 48.71(18) . . . . ?
N1 N2 C15 O2 -173.02(14) . . . . ?
C16 N2 C15 O2 20.8(2) . . . . ?
N1 N2 C15 C10 14.0(2) . . . . ?
C16 N2 C15 C10 -152.10(15) . . . . ?
C9 C10 C15 O2 -165.09(19) . . . . ?
C9 C10 C15 N2 7.8(3) . . . . ?
C15 N2 C16 C23 21.9(2) . . . . ?
N1 N2 C16 C23 -145.06(13) . . . . ?
C15 N2 C16 C17 -158.90(13) . . . . ?
N1 N2 C16 C17 34.14(16) . . . . ?
C23 C16 C17 C20 -4.84(19) . . . . ?
N2 C16 C17 C20 175.96(12) . . . . ?
C23 C16 C17 C6 176.44(12) . . . . ?
N2 C16 C17 C6 -2.77(18) . . . . ?
C7 C6 C17 C20 166.12(13) . . . . ?
C5 C6 C17 C20 -13.92(19) . . . . ?
C7 C6 C17 C16 -15.23(19) . . . . ?
C5 C6 C17 C16 164.74(12) . . . . ?
C2 C1 C18 C19 -0.2(3) . . . . ?
C1 C18 C19 C4 -0.5(2) . . . . ?
C3 C4 C19 C18 1.1(2) . . . . ?
C5 C4 C19 C18 -177.41(13) . . . . ?
C16 C17 C20 C21 2.7(2) . . . . ?
C6 C17 C20 C21 -178.58(13) . . . . ?
C17 C20 C21 C22 1.1(2) . . . . ?
C20 C21 C22 C23 -3.1(2) . . . . ?
C21 C22 C23 C16 1.0(2) . . . . ?
C17 C16 C23 C22 3.0(2) . . . . ?
N2 C16 C23 C22 -177.81(13) . . . . ?
C13 C14 C24 C25 1.3(2) . . . . ?
C7 C14 C24 C25 -179.05(14) . . . . ?
C12 C11 C25 C24 -1.1(3) . . . . ?
F1 C11 C25 C24 178.34(14) . . . . ?
C14 C24 C25 C11 -0.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C23 H11 O2 0.95 2.41 2.8832(18) 110.5 .
C23 H11 O2 0.95 2.41 2.8832(18) 110.5 .

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.048

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1434966'
_audit_update_record             
;
2015-11-03 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H30 N6 O8'
_chemical_formula_weight         794.76

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   22.748(6)
_cell_length_b                   10.773(3)
_cell_length_c                   15.613(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.346(8)
_cell_angle_gamma                90
_cell_volume                     3737.9(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    0(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34212
_diffrn_reflns_av_unetI/netI     0.1224
_diffrn_reflns_av_R_equivalents  0.1066
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.101
_diffrn_reflns_theta_max         28.619
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             9084
_reflns_number_gt                4523
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1267P)²+6.3489P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9084
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2069
_refine_ls_R_factor_gt           0.1076
_refine_ls_wR_factor_ref         0.3199
_refine_ls_wR_factor_gt          0.2679
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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
O107 O 0.5890(3) 0.4532(5) 1.2327(3) 0.0985(15) Uani 1 1 d . . . . .
C132 C 0.7420(2) 0.7024(5) 0.7917(3) 0.0498(12) Uani 1 1 d . . . . .
H132 H 0.7738 0.6684 0.7685 0.060 Uiso 1 1 calc R U . . .
O105 O 0.74780(15) 1.0641(3) 0.8903(2) 0.0606(9) Uani 1 1 d . . . . .
O108 O 0.4952(3) 0.5058(5) 1.2140(4) 0.1097(18) Uani 1 1 d . . . . .
C104 C 0.9820(2) 0.2716(5) 0.8995(3) 0.0490(11) Uani 1 1 d . . . . .
H104 H 0.9995 0.2319 0.9532 0.059 Uiso 1 1 calc R U . . .
C120 C 0.8162(2) 0.3394(5) 1.0267(3) 0.0518(12) Uani 1 1 d . . . . .
H120 H 0.8165 0.3360 0.9660 0.062 Uiso 1 1 calc R U . . .
C122 C 0.7947(2) 0.2402(5) 1.0660(3) 0.0552(13) Uani 1 1 d . . . . .
H122 H 0.7807 0.1679 1.0330 0.066 Uiso 1 1 calc R U . . .
O103 O 0.7557(3) 0.0470(5) 1.1499(4) 0.1067(17) Uani 1 1 d . . . . .
O104 O 0.7706(3) 0.1444(5) 1.2727(4) 0.1147(19) Uani 1 1 d . . . . .
C119 C 0.8364(2) 0.4456(5) 1.1635(3) 0.0524(12) Uani 1 1 d . . . . .
H119 H 0.8518 0.5159 1.1978 0.063 Uiso 1 1 calc R U . . .
O101 O 0.88395(16) 0.6240(4) 0.7532(2) 0.0646(10) Uani 1 1 d . . . . .
C101 C 0.9317(2) 0.3853(5) 0.7419(3) 0.0551(13) Uani 1 1 d . . . . .
H101 H 0.9148 0.4249 0.6879 0.066 Uiso 1 1 calc R U . . .
C102 C 0.9634(2) 0.2754(6) 0.7422(4) 0.0606(14) Uani 1 1 d . . . . .
H102 H 0.9672 0.2378 0.6886 0.073 Uiso 1 1 calc R U . . .
O102 O 0.95467(14) 0.3787(3) 1.0534(2) 0.0519(8) Uani 1 1 d . . . . .
C115 C 0.9153(2) 0.8230(5) 0.8744(4) 0.0557(13) Uani 1 1 d . . . . .
H115 H 0.9307 0.8003 0.8247 0.067 Uiso 1 1 calc R U . . .
C114 C 0.9163(3) 0.9446(6) 0.9010(4) 0.0695(16) Uani 1 1 d . . . . .
H114 H 0.9329 1.0060 0.8695 0.083 Uiso 1 1 calc R U . . .
C112 C 0.8697(2) 0.8895(5) 1.0182(3) 0.0566(13) Uani 1 1 d . . . . .
H112 H 0.8539 0.9131 1.0674 0.068 Uiso 1 1 calc R U . . .
C134 C 0.6436(2) 0.6815(5) 0.8245(3) 0.0455(11) Uani 1 1 d . . . . .
H134 H 0.6081 0.6342 0.8226 0.055 Uiso 1 1 calc R U . . .
C135 C 0.64930(18) 0.7987(4) 0.8624(3) 0.0382(9) Uani 1 1 d . . . . .
N105 N 0.61763(16) 0.9486(4) 0.9569(2) 0.0435(9) Uani 1 1 d . . . . .
C147 C 0.59907(18) 0.9669(4) 1.0385(3) 0.0408(10) Uani 1 1 d . . . . .
C149 C 0.5321(2) 0.8409(5) 1.1133(3) 0.0495(12) Uani 1 1 d . . . . .
H149 H 0.5043 0.9079 1.1058 0.059 Uiso 1 1 calc R U . . .
C131 C 0.74752(19) 0.8198(5) 0.8278(3) 0.0458(11) Uani 1 1 d . . . . .
H131 H 0.7824 0.8682 0.8274 0.055 Uiso 1 1 calc R U . . .
N104 N 0.66205(16) 1.0312(4) 0.9394(2) 0.0438(9) Uani 1 1 d . . . . .
C140 C 0.6622(3) 1.2511(5) 0.8979(4) 0.0613(14) Uani 1 1 d . . . . .
H140 H 0.6828 1.2319 0.8527 0.074 Uiso 1 1 calc R U . . .
C141 C 0.6471(3) 1.3713(6) 0.9125(4) 0.0791(18) Uani 1 1 d . . . . .
H141 H 0.6580 1.4361 0.8777 0.095 Uiso 1 1 calc R U . . .
C142 C 0.6162(3) 1.3994(6) 0.9770(4) 0.084(2) Uani 1 1 d . . . . .
H142 H 0.6058 1.4831 0.9858 0.100 Uiso 1 1 calc R U . . .
C150 C 0.6259(2) 0.7545(5) 1.0947(3) 0.0472(11) Uani 1 1 d . . . . .
H150 H 0.6621 0.7614 1.0741 0.057 Uiso 1 1 calc R U . . .
O106 O 0.55582(13) 0.7876(3) 0.9081(2) 0.0532(9) Uani 1 1 d . . . . .
C103 C 0.9891(2) 0.2215(5) 0.8209(4) 0.0615(14) Uani 1 1 d . . . . .
H103 H 1.0124 0.1481 0.8214 0.074 Uiso 1 1 calc R U . . .
C105 C 0.94941(17) 0.3798(4) 0.8994(3) 0.0397(10) Uani 1 1 d . . . . .
N102 N 0.89847(15) 0.5275(4) 0.9738(2) 0.0408(9) Uani 1 1 d . . . . .
C118 C 0.83759(18) 0.4445(4) 1.0748(3) 0.0410(10) Uani 1 1 d . . . . .
N101 N 0.89059(15) 0.6051(4) 0.8992(2) 0.0418(9) Uani 1 1 d . . . . .
C107 C 0.89693(19) 0.5610(5) 0.8195(3) 0.0462(11) Uani 1 1 d . . . . .
C106 C 0.92472(18) 0.4374(5) 0.8196(3) 0.0429(10) Uani 1 1 d . . . . .
C113 C 0.8937(3) 0.9791(6) 0.9725(4) 0.0705(16) Uani 1 1 d . . . . .
H113 H 0.8946 1.0635 0.9903 0.085 Uiso 1 1 calc R U . . .
C133 C 0.6900(2) 0.6338(5) 0.7894(3) 0.0523(12) Uani 1 1 d . . . . .
H133 H 0.6861 0.5536 0.7635 0.063 Uiso 1 1 calc R U . . .
C138 C 0.60222(18) 0.8422(4) 0.9063(3) 0.0415(10) Uani 1 1 d . . . . .
C148 C 0.58524(19) 0.8531(4) 1.0829(3) 0.0418(10) Uani 1 1 d . . . . .
C151 C 0.5192(2) 0.7347(5) 1.1534(3) 0.0550(13) Uani 1 1 d . . . . .
H151 H 0.4829 0.7270 1.1738 0.066 Uiso 1 1 calc R U . . .
C152 C 0.5603(2) 0.6391(5) 1.1636(3) 0.0546(13) Uani 1 1 d . . . . .
N106 N 0.5472(3) 0.5248(5) 1.2069(3) 0.0723(14) Uani 1 1 d . . . . .
C136 C 0.70181(18) 0.8663(4) 0.8645(3) 0.0374(9) Uani 1 1 d . . . . .
C137 C 0.7073(2) 0.9937(5) 0.8999(3) 0.0443(11) Uani 1 1 d . . . . .
C139 C 0.6466(2) 1.1580(5) 0.9506(3) 0.0479(11) Uani 1 1 d . . . . .
C143 C 0.6004(3) 1.3066(5) 1.0288(4) 0.0689(16) Uani 1 1 d . . . . .
H143 H 0.5790 1.3265 1.0731 0.083 Uiso 1 1 calc R U . . .
C144 C 0.6157(2) 1.1842(5) 1.0159(3) 0.0506(12) Uani 1 1 d . . . . .
C145 C 0.5995(2) 1.0835(5) 1.0700(3) 0.0467(11) Uani 1 1 d . . . . .
C153 C 0.6140(2) 0.6474(5) 1.1357(3) 0.0506(12) Uani 1 1 d . . . . .
H153 H 0.6419 0.5807 1.1448 0.061 Uiso 1 1 calc R U . . .
C108 C 0.93744(17) 0.4275(4) 0.9824(3) 0.0386(10) Uani 1 1 d . . . . .
C109 C 0.85938(18) 0.5525(4) 1.0324(3) 0.0401(10) Uani 1 1 d . . . . .
C123 C 0.7936(2) 0.2468(5) 1.1532(3) 0.0530(13) Uani 1 1 d . . . . .
N103 N 0.7712(2) 0.1391(6) 1.1948(4) 0.0739(14) Uani 1 1 d . . . . .
C121 C 0.8137(2) 0.3483(6) 1.2026(3) 0.0603(14) Uani 1 1 d . . . . .
H121 H 0.8120 0.3517 1.2628 0.072 Uiso 1 1 calc R U . . .
C110 C 0.89157(18) 0.7343(4) 0.9211(3) 0.0418(10) Uani 1 1 d . . . . .
C111 C 0.86818(18) 0.7659(5) 0.9937(3) 0.0428(10) Uani 1 1 d . . . . .
C117 C 0.84210(19) 0.6703(5) 1.0402(3) 0.0449(11) Uani 1 1 d . . . . .
C146 C 0.5874(2) 1.1135(5) 1.1583(3) 0.0576(13) Uani 1 1 d . . . . .
H14A H 0.5900 1.2034 1.1677 0.086 Uiso 1 1 calc R U . . .
H14B H 0.5470 1.0846 1.1613 0.086 Uiso 1 1 calc R U . . .
H14C H 0.6173 1.0719 1.2038 0.086 Uiso 1 1 calc R U . . .
C116 C 0.7940(2) 0.7076(6) 1.0882(4) 0.0610(14) Uani 1 1 d . . . . .
H11A H 0.7890 0.7980 1.0854 0.092 Uiso 1 1 calc R U . . .
H11B H 0.7559 0.6676 1.0608 0.092 Uiso 1 1 calc R U . . .
H11C H 0.8058 0.6815 1.1496 0.092 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O107 N106 1.225(7) . ?
C132 C131 1.379(7) . ?
C132 C133 1.389(7) . ?
C132 H132 0.9500 . ?
O105 C137 1.227(5) . ?
O108 N106 1.227(7) . ?
C104 C103 1.380(7) . ?
C104 C105 1.382(7) . ?
C104 H104 0.9500 . ?
C120 C122 1.373(7) . ?
C120 C118 1.388(7) . ?
C120 H120 0.9500 . ?
C122 C123 1.370(7) . ?
C122 H122 0.9500 . ?
O103 N103 1.223(7) . ?
O104 N103 1.222(7) . ?
C119 C121 1.369(7) . ?
C119 C118 1.390(6) . ?
C119 H119 0.9500 . ?
O101 C107 1.220(5) . ?
C101 C106 1.377(6) . ?
C101 C102 1.386(8) . ?
C101 H101 0.9500 . ?
C102 C103 1.372(8) . ?
C102 H102 0.9500 . ?
O102 C108 1.215(5) . ?
C115 C114 1.373(8) . ?
C115 C110 1.380(7) . ?
C115 H115 0.9500 . ?
C114 C113 1.377(8) . ?
C114 H114 0.9500 . ?
C112 C113 1.380(8) . ?
C112 C111 1.383(7) . ?
C112 H112 0.9500 . ?
C134 C133 1.387(6) . ?
C134 C135 1.390(6) . ?
C134 H134 0.9500 . ?
C135 C136 1.393(6) . ?
C135 C138 1.466(6) . ?
N105 C138 1.394(6) . ?
N105 N104 1.416(5) . ?
N105 C147 1.439(5) . ?
C147 C145 1.348(7) . ?
C147 C148 1.475(6) . ?
C149 C151 1.367(7) . ?
C149 C148 1.395(6) . ?
C149 H149 0.9500 . ?
C131 C136 1.384(6) . ?
C131 H131 0.9500 . ?
N104 C137 1.369(6) . ?
N104 C139 1.430(6) . ?
C140 C141 1.371(8) . ?
C140 C139 1.391(7) . ?
C140 H140 0.9500 . ?
C141 C142 1.378(9) . ?
C141 H141 0.9500 . ?
C142 C143 1.382(9) . ?
C142 H142 0.9500 . ?
C150 C153 1.375(7) . ?
C150 C148 1.394(6) . ?
C150 H150 0.9500 . ?
O106 C138 1.213(5) . ?
C103 H103 0.9500 . ?
C105 C106 1.398(6) . ?
C105 C108 1.472(6) . ?
N102 C108 1.383(6) . ?
N102 N101 1.414(5) . ?
N102 C109 1.431(5) . ?
C118 C109 1.476(6) . ?
N101 C107 1.367(6) . ?
N101 C110 1.432(6) . ?
C107 C106 1.474(7) . ?
C113 H113 0.9500 . ?
C133 H133 0.9500 . ?
C151 C152 1.376(8) . ?
C151 H151 0.9500 . ?
C152 C153 1.384(7) . ?
C152 N106 1.466(7) . ?
C136 C137 1.475(6) . ?
C139 C144 1.385(7) . ?
C143 C144 1.391(7) . ?
C143 H143 0.9500 . ?
C144 C145 1.469(7) . ?
C145 C146 1.499(7) . ?
C153 H153 0.9500 . ?
C109 C117 1.342(7) . ?
C123 C121 1.360(8) . ?
C123 N103 1.471(7) . ?
C121 H121 0.9500 . ?
C110 C111 1.393(6) . ?
C111 C117 1.458(7) . ?
C117 C116 1.507(6) . ?
C146 H14A 0.9800 . ?
C146 H14B 0.9800 . ?
C146 H14C 0.9800 . ?
C116 H11A 0.9800 . ?
C116 H11B 0.9800 . ?
C116 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C131 C132 C133 120.1(4) . . ?
C131 C132 H132 119.9 . . ?
C133 C132 H132 119.9 . . ?
C103 C104 C105 119.6(5) . . ?
C103 C104 H104 120.2 . . ?
C105 C104 H104 120.2 . . ?
C122 C120 C118 120.7(4) . . ?
C122 C120 H120 119.6 . . ?
C118 C120 H120 119.6 . . ?
C123 C122 C120 119.2(5) . . ?
C123 C122 H122 120.4 . . ?
C120 C122 H122 120.4 . . ?
C121 C119 C118 121.8(5) . . ?
C121 C119 H119 119.1 . . ?
C118 C119 H119 119.1 . . ?
C106 C101 C102 120.2(5) . . ?
C106 C101 H101 119.9 . . ?
C102 C101 H101 119.9 . . ?
C103 C102 C101 119.2(5) . . ?
C103 C102 H102 120.4 . . ?
C101 C102 H102 120.4 . . ?
C114 C115 C110 118.9(5) . . ?
C114 C115 H115 120.5 . . ?
C110 C115 H115 120.5 . . ?
C115 C114 C113 121.2(5) . . ?
C115 C114 H114 119.4 . . ?
C113 C114 H114 119.4 . . ?
C113 C112 C111 121.3(5) . . ?
C113 C112 H112 119.3 . . ?
C111 C112 H112 119.3 . . ?
C133 C134 C135 119.7(4) . . ?
C133 C134 H134 120.2 . . ?
C135 C134 H134 120.2 . . ?
C134 C135 C136 119.1(4) . . ?
C134 C135 C138 118.6(4) . . ?
C136 C135 C138 122.1(4) . . ?
C138 N105 N104 120.7(3) . . ?
C138 N105 C147 121.9(4) . . ?
N104 N105 C147 116.2(3) . . ?
C145 C147 N105 118.0(4) . . ?
C145 C147 C148 126.1(4) . . ?
N105 C147 C148 115.8(4) . . ?
C151 C149 C148 121.4(5) . . ?
C151 C149 H149 119.3 . . ?
C148 C149 H149 119.3 . . ?
C132 C131 C136 119.3(4) . . ?
C132 C131 H131 120.3 . . ?
C136 C131 H131 120.3 . . ?
C137 N104 N105 122.5(4) . . ?
C137 N104 C139 124.5(4) . . ?
N105 N104 C139 111.8(4) . . ?
C141 C140 C139 118.6(5) . . ?
C141 C140 H140 120.7 . . ?
C139 C140 H140 120.7 . . ?
C140 C141 C142 120.9(6) . . ?
C140 C141 H141 119.6 . . ?
C142 C141 H141 119.6 . . ?
C141 C142 C143 120.4(6) . . ?
C141 C142 H142 119.8 . . ?
C143 C142 H142 119.8 . . ?
C153 C150 C148 120.7(4) . . ?
C153 C150 H150 119.7 . . ?
C148 C150 H150 119.7 . . ?
C102 C103 C104 121.4(5) . . ?
C102 C103 H103 119.3 . . ?
C104 C103 H103 119.3 . . ?
C104 C105 C106 119.3(4) . . ?
C104 C105 C108 119.6(4) . . ?
C106 C105 C108 121.0(4) . . ?
C108 N102 N101 120.4(3) . . ?
C108 N102 C109 123.9(4) . . ?
N101 N102 C109 115.4(3) . . ?
C120 C118 C119 117.8(4) . . ?
C120 C118 C109 120.9(4) . . ?
C119 C118 C109 121.3(4) . . ?
C107 N101 N102 121.6(4) . . ?
C107 N101 C110 123.8(4) . . ?
N102 N101 C110 112.6(3) . . ?
O101 C107 N101 121.7(5) . . ?
O101 C107 C106 122.0(4) . . ?
N101 C107 C106 116.2(4) . . ?
C101 C106 C105 120.3(5) . . ?
C101 C106 C107 119.8(4) . . ?
C105 C106 C107 119.5(4) . . ?
C114 C113 C112 119.2(6) . . ?
C114 C113 H113 120.4 . . ?
C112 C113 H113 120.4 . . ?
C134 C133 C132 120.5(5) . . ?
C134 C133 H133 119.7 . . ?
C132 C133 H133 119.7 . . ?
O106 C138 N105 120.0(4) . . ?
O106 C138 C135 125.6(4) . . ?
N105 C138 C135 114.0(4) . . ?
C150 C148 C149 118.8(4) . . ?
C150 C148 C147 119.6(4) . . ?
C149 C148 C147 121.6(4) . . ?
C149 C151 C152 118.2(4) . . ?
C149 C151 H151 120.9 . . ?
C152 C151 H151 120.9 . . ?
C151 C152 C153 122.6(5) . . ?
C151 C152 N106 118.8(5) . . ?
C153 C152 N106 118.6(5) . . ?
O107 N106 O108 124.1(6) . . ?
O107 N106 C152 117.4(5) . . ?
O108 N106 C152 118.5(6) . . ?
C131 C136 C135 121.2(4) . . ?
C131 C136 C137 118.8(4) . . ?
C135 C136 C137 119.8(4) . . ?
O105 C137 N104 121.9(5) . . ?
O105 C137 C136 122.3(4) . . ?
N104 C137 C136 115.6(4) . . ?
C144 C139 C140 121.5(5) . . ?
C144 C139 N104 117.5(4) . . ?
C140 C139 N104 121.0(4) . . ?
C142 C143 C144 119.8(5) . . ?
C142 C143 H143 120.1 . . ?
C144 C143 H143 120.1 . . ?
C139 C144 C143 118.8(5) . . ?
C139 C144 C145 120.1(4) . . ?
C143 C144 C145 121.0(5) . . ?
C147 C145 C144 117.5(4) . . ?
C147 C145 C146 123.2(5) . . ?
C144 C145 C146 119.2(4) . . ?
C150 C153 C152 118.4(5) . . ?
C150 C153 H153 120.8 . . ?
C152 C153 H153 120.8 . . ?
O102 C108 N102 120.0(4) . . ?
O102 C108 C105 124.6(4) . . ?
N102 C108 C105 115.0(4) . . ?
C117 C109 N102 118.0(4) . . ?
C117 C109 C118 124.9(4) . . ?
N102 C109 C118 116.9(4) . . ?
C121 C123 C122 122.0(5) . . ?
C121 C123 N103 119.3(5) . . ?
C122 C123 N103 118.6(5) . . ?
O104 N103 O103 123.0(6) . . ?
O104 N103 C123 118.8(6) . . ?
O103 N103 C123 118.2(5) . . ?
C123 C121 C119 118.5(5) . . ?
C123 C121 H121 120.8 . . ?
C119 C121 H121 120.8 . . ?
C115 C110 C111 121.4(5) . . ?
C115 C110 N101 122.3(4) . . ?
C111 C110 N101 116.3(4) . . ?
C112 C111 C110 118.0(4) . . ?
C112 C111 C117 122.1(4) . . ?
C110 C111 C117 120.0(4) . . ?
C109 C117 C111 117.7(4) . . ?
C109 C117 C116 123.7(4) . . ?
C111 C117 C116 118.4(4) . . ?
C145 C146 H14A 109.5 . . ?
C145 C146 H14B 109.5 . . ?
H14A C146 H14B 109.5 . . ?
C145 C146 H14C 109.5 . . ?
H14A C146 H14C 109.5 . . ?
H14B C146 H14C 109.5 . . ?
C117 C116 H11A 109.5 . . ?
C117 C116 H11B 109.5 . . ?
H11A C116 H11B 109.5 . . ?
C117 C116 H11C 109.5 . . ?
H11A C116 H11C 109.5 . . ?
H11B C116 H11C 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
C118 C120 C122 C123 1.1(7) . . . . ?
C106 C101 C102 C103 -2.0(8) . . . . ?
C110 C115 C114 C113 -0.6(8) . . . . ?
C133 C134 C135 C136 0.0(6) . . . . ?
C133 C134 C135 C138 -174.4(4) . . . . ?
C138 N105 C147 C145 -160.4(4) . . . . ?
N104 N105 C147 C145 31.9(6) . . . . ?
C138 N105 C147 C148 23.7(6) . . . . ?
N104 N105 C147 C148 -144.0(4) . . . . ?
C133 C132 C131 C136 2.5(7) . . . . ?
C138 N105 N104 C137 -26.2(6) . . . . ?
C147 N105 N104 C137 141.6(4) . . . . ?
C138 N105 N104 C139 141.7(4) . . . . ?
C147 N105 N104 C139 -50.5(5) . . . . ?
C139 C140 C141 C142 -1.1(9) . . . . ?
C140 C141 C142 C143 0.6(10) . . . . ?
C101 C102 C103 C104 2.8(8) . . . . ?
C105 C104 C103 C102 -1.4(7) . . . . ?
C103 C104 C105 C106 -0.7(7) . . . . ?
C103 C104 C105 C108 174.8(4) . . . . ?
C122 C120 C118 C119 0.0(7) . . . . ?
C122 C120 C118 C109 -178.5(4) . . . . ?
C121 C119 C118 C120 -1.5(7) . . . . ?
C121 C119 C118 C109 176.9(4) . . . . ?
C108 N102 N101 C107 29.7(6) . . . . ?
C109 N102 N101 C107 -144.0(4) . . . . ?
C108 N102 N101 C110 -134.9(4) . . . . ?
C109 N102 N101 C110 51.4(5) . . . . ?
N102 N101 C107 O101 172.1(4) . . . . ?
C110 N101 C107 O101 -25.1(6) . . . . ?
N102 N101 C107 C106 -12.6(6) . . . . ?
C110 N101 C107 C106 150.2(4) . . . . ?
C102 C101 C106 C105 -0.1(7) . . . . ?
C102 C101 C106 C107 173.2(4) . . . . ?
C104 C105 C106 C101 1.4(6) . . . . ?
C108 C105 C106 C101 -174.0(4) . . . . ?
C104 C105 C106 C107 -171.9(4) . . . . ?
C108 C105 C106 C107 12.7(6) . . . . ?
O101 C107 C106 C101 -5.9(7) . . . . ?
N101 C107 C106 C101 178.8(4) . . . . ?
O101 C107 C106 C105 167.5(4) . . . . ?
N101 C107 C106 C105 -7.9(6) . . . . ?
C115 C114 C113 C112 0.1(9) . . . . ?
C111 C112 C113 C114 0.3(8) . . . . ?
C135 C134 C133 C132 -0.1(7) . . . . ?
C131 C132 C133 C134 -1.1(7) . . . . ?
N104 N105 C138 O106 -163.3(4) . . . . ?
C147 N105 C138 O106 29.6(6) . . . . ?
N104 N105 C138 C135 23.5(6) . . . . ?
C147 N105 C138 C135 -143.6(4) . . . . ?
C134 C135 C138 O106 -4.9(7) . . . . ?
C136 C135 C138 O106 -179.1(4) . . . . ?
C134 C135 C138 N105 167.8(4) . . . . ?
C136 C135 C138 N105 -6.4(6) . . . . ?
C153 C150 C148 C149 -0.3(7) . . . . ?
C153 C150 C148 C147 -179.9(4) . . . . ?
C151 C149 C148 C150 -0.4(7) . . . . ?
C151 C149 C148 C147 179.2(4) . . . . ?
C145 C147 C148 C150 -126.6(5) . . . . ?
N105 C147 C148 C150 49.0(6) . . . . ?
C145 C147 C148 C149 53.8(6) . . . . ?
N105 C147 C148 C149 -130.6(4) . . . . ?
C148 C149 C151 C152 0.2(7) . . . . ?
C149 C151 C152 C153 0.8(8) . . . . ?
C149 C151 C152 N106 179.7(4) . . . . ?
C151 C152 N106 O107 -164.1(5) . . . . ?
C153 C152 N106 O107 14.9(7) . . . . ?
C151 C152 N106 O108 17.0(7) . . . . ?
C153 C152 N106 O108 -164.0(5) . . . . ?
C132 C131 C136 C135 -2.6(6) . . . . ?
C132 C131 C136 C137 -177.8(4) . . . . ?
C134 C135 C136 C131 1.4(6) . . . . ?
C138 C135 C136 C131 175.6(4) . . . . ?
C134 C135 C136 C137 176.5(4) . . . . ?
C138 C135 C136 C137 -9.4(6) . . . . ?
N105 N104 C137 O105 -175.1(4) . . . . ?
C139 N104 C137 O105 18.6(7) . . . . ?
N105 N104 C137 C136 8.9(6) . . . . ?
C139 N104 C137 C136 -157.4(4) . . . . ?
C131 C136 C137 O105 7.4(7) . . . . ?
C135 C136 C137 O105 -167.8(4) . . . . ?
C131 C136 C137 N104 -176.6(4) . . . . ?
C135 C136 C137 N104 8.2(6) . . . . ?
C141 C140 C139 C144 0.9(8) . . . . ?
C141 C140 C139 N104 -178.9(5) . . . . ?
C137 N104 C139 C144 -158.1(4) . . . . ?
N105 N104 C139 C144 34.3(5) . . . . ?
C137 N104 C139 C140 21.7(7) . . . . ?
N105 N104 C139 C140 -145.9(4) . . . . ?
C141 C142 C143 C144 0.1(10) . . . . ?
C140 C139 C144 C143 -0.3(8) . . . . ?
N104 C139 C144 C143 179.6(4) . . . . ?
C140 C139 C144 C145 179.5(4) . . . . ?
N104 C139 C144 C145 -0.7(7) . . . . ?
C142 C143 C144 C139 -0.3(8) . . . . ?
C142 C143 C144 C145 -180.0(5) . . . . ?
N105 C147 C145 C144 3.3(6) . . . . ?
C148 C147 C145 C144 178.8(4) . . . . ?
N105 C147 C145 C146 -173.5(4) . . . . ?
C148 C147 C145 C146 2.0(7) . . . . ?
C139 C144 C145 C147 -19.2(7) . . . . ?
C143 C144 C145 C147 160.5(5) . . . . ?
C139 C144 C145 C146 157.7(4) . . . . ?
C143 C144 C145 C146 -22.6(7) . . . . ?
C148 C150 C153 C152 1.2(7) . . . . ?
C151 C152 C153 C150 -1.4(7) . . . . ?
N106 C152 C153 C150 179.6(4) . . . . ?
N101 N102 C108 O102 163.2(4) . . . . ?
C109 N102 C108 O102 -23.6(6) . . . . ?
N101 N102 C108 C105 -23.4(6) . . . . ?
C109 N102 C108 C105 149.7(4) . . . . ?
C104 C105 C108 O102 0.5(7) . . . . ?
C106 C105 C108 O102 175.9(4) . . . . ?
C104 C105 C108 N102 -172.5(4) . . . . ?
C106 C105 C108 N102 2.9(6) . . . . ?
C108 N102 C109 C117 154.2(4) . . . . ?
N101 N102 C109 C117 -32.3(5) . . . . ?
C108 N102 C109 C118 -30.1(6) . . . . ?
N101 N102 C109 C118 143.3(4) . . . . ?
C120 C118 C109 C117 129.9(5) . . . . ?
C119 C118 C109 C117 -48.5(6) . . . . ?
C120 C118 C109 N102 -45.4(6) . . . . ?
C119 C118 C109 N102 136.2(4) . . . . ?
C120 C122 C123 C121 -0.6(8) . . . . ?
C120 C122 C123 N103 -179.1(4) . . . . ?
C121 C123 N103 O104 0.9(8) . . . . ?
C122 C123 N103 O104 179.4(5) . . . . ?
C121 C123 N103 O103 -177.0(6) . . . . ?
C122 C123 N103 O103 1.5(8) . . . . ?
C122 C123 C121 C119 -0.9(8) . . . . ?
N103 C123 C121 C119 177.6(5) . . . . ?
C118 C119 C121 C123 2.0(8) . . . . ?
C114 C115 C110 C111 0.7(7) . . . . ?
C114 C115 C110 N101 -178.0(5) . . . . ?
C107 N101 C110 C115 -18.6(6) . . . . ?
N102 N101 C110 C115 145.6(4) . . . . ?
C107 N101 C110 C111 162.6(4) . . . . ?
N102 N101 C110 C111 -33.2(5) . . . . ?
C113 C112 C111 C110 -0.1(7) . . . . ?
C113 C112 C111 C117 -179.0(5) . . . . ?
C115 C110 C111 C112 -0.4(6) . . . . ?
N101 C110 C111 C112 178.5(4) . . . . ?
C115 C110 C111 C117 178.5(4) . . . . ?
N101 C110 C111 C117 -2.7(6) . . . . ?
N102 C109 C117 C111 -4.7(6) . . . . ?
C118 C109 C117 C111 -180.0(4) . . . . ?
N102 C109 C117 C116 170.3(4) . . . . ?
C118 C109 C117 C116 -5.0(7) . . . . ?
C112 C111 C117 C109 -158.5(4) . . . . ?
C110 C111 C117 C109 22.7(6) . . . . ?
C112 C111 C117 C116 26.2(6) . . . . ?
C110 C111 C117 C116 -152.6(4) . . . . ?

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.077

_shelxl_version_number           2014-3

