# 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_gz150209
_database_code_depnum_ccdc_archive 'CCDC 1053771'
_audit_update_record             
;
2015-03-16 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;
_audit_creation_date             2015-02-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H10 N4 O3'
_chemical_formula_sum            'C13 H10 N4 O3'
_chemical_formula_weight         270.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.21681(17)
_cell_length_b                   7.14117(12)
_cell_length_c                   19.9378(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.7636(15)
_cell_angle_gamma                90
_cell_volume                     1310.76(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6914
_cell_measurement_temperature    288.91(10)
_cell_measurement_theta_max      71.5480
_cell_measurement_theta_min      5.1680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9919
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.403
_diffrn_reflns_theta_min         4.804
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      288.91(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -99.0000   90.0000 75

#__ type_ start__ end____ width___ exp.time_
  2 omega  -35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -19.0000   30.0000 101

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -99.0000  -30.0000 75

#__ type_ start__ end____ width___ exp.time_
  4 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -57.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega   39.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000  120.0000 71

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000   30.0000 71

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -112.0000  -30.0000 78

#__ type_ start__ end____ width___ exp.time_
 14 omega   87.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 91

#__ type_ start__ end____ width___ exp.time_
 15 omega  101.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  112.0000   90.0000 77

#__ type_ start__ end____ width___ exp.time_
 16 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   77.0000   90.0000 94

#__ type_ start__ end____ width___ exp.time_
 17 omega   57.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  178.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
 18 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   57.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
 19 omega  -32.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203  -38.0000  150.0000 88

#__ type_ start__ end____ width___ exp.time_
 20 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7203   57.0000 -150.0000 84

#__ type_ start__ end____ width___ exp.time_
 21 omega   70.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 108

#__ type_ start__ end____ width___ exp.time_
 22 omega   91.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 85

#__ type_ start__ end____ width___ exp.time_
 23 omega   70.00  170.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0165474000
_diffrn_orient_matrix_UB_12      -0.1917369000
_diffrn_orient_matrix_UB_13      -0.0349917000
_diffrn_orient_matrix_UB_21      0.0425973000
_diffrn_orient_matrix_UB_22      -0.0987518000
_diffrn_orient_matrix_UB_23      0.0667680000
_diffrn_orient_matrix_UB_31      -0.1609241000
_diffrn_orient_matrix_UB_32      -0.0064612000
_diffrn_orient_matrix_UB_33      0.0174192000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2386
_reflns_number_total             2514
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2514
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.019
_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)+(0.0723P)²+0.3989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1231
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_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
O14 O 0.15167(11) 0.12794(15) 0.02621(5) 0.0426(3) Uani 1 1 d . . . . .
N1 N 0.34532(13) 0.23989(17) -0.03059(6) 0.0380(3) Uani 1 1 d . . . . .
H1 H 0.4039 0.2648 0.0031 0.046 Uiso 1 1 calc R . . . .
N11 N -0.01927(14) 0.40793(19) -0.10033(7) 0.0466(3) Uani 1 1 d . . . . .
C10 C -0.00684(14) 0.20146(19) -0.10939(7) 0.0365(3) Uani 1 1 d . . . . .
H10A H -0.0409 0.1691 -0.1547 0.044 Uiso 1 1 calc R . . . .
H10B H -0.0694 0.1392 -0.0786 0.044 Uiso 1 1 calc R . . . .
O13 O 0.08035(14) 0.49299(17) -0.07295(8) 0.0637(4) Uani 1 1 d . . . . .
C9 C 0.21141(14) 0.16829(18) -0.02500(6) 0.0322(3) Uani 1 1 d . . . . .
C8 C 0.14821(13) 0.12930(18) -0.09727(6) 0.0302(3) Uani 1 1 d . . . . .
C16 C 0.27362(16) -0.1795(2) -0.07579(7) 0.0380(3) Uani 1 1 d . . . . .
N17 N 0.37728(16) -0.2456(2) -0.05392(8) 0.0558(4) Uani 1 1 d . . . . .
C15 C 0.13886(14) -0.09021(18) -0.10242(6) 0.0321(3) Uani 1 1 d . . . . .
H15 H 0.0591 -0.1324 -0.0753 0.039 Uiso 1 1 calc R . . . .
C18 C 0.10881(17) -0.1545(2) -0.17182(8) 0.0441(4) Uani 1 1 d . . . . .
C2 C 0.37849(15) 0.26944(19) -0.09805(7) 0.0366(3) Uani 1 1 d . . . . .
C7 C 0.26298(14) 0.21202(18) -0.14006(7) 0.0340(3) Uani 1 1 d . . . . .
C6 C 0.26495(18) 0.2383(2) -0.20860(7) 0.0424(4) Uani 1 1 d . . . . .
H6 H 0.1864 0.2016 -0.2366 0.051 Uiso 1 1 calc R . . . .
C5 C 0.3873(2) 0.3212(2) -0.23531(8) 0.0509(4) Uani 1 1 d . . . . .
C3 C 0.50158(17) 0.3467(2) -0.12313(9) 0.0485(4) Uani 1 1 d . . . . .
H3 H 0.5803 0.3819 -0.0950 0.058 Uiso 1 1 calc R . . . .
O12 O -0.13173(17) 0.4796(2) -0.12135(11) 0.0959(6) Uani 1 1 d . . . . .
C4 C 0.50326(19) 0.3700(2) -0.19226(9) 0.0554(5) Uani 1 1 d . . . . .
H4 H 0.5858 0.4205 -0.2103 0.067 Uiso 1 1 calc R . . . .
N19 N 0.0871(2) -0.2042(3) -0.22528(8) 0.0739(5) Uani 1 1 d . . . . .
C20 C 0.3883(3) 0.3578(3) -0.31024(10) 0.0789(7) Uani 1 1 d . . . . .
H20A H 0.3191 0.2773 -0.3333 0.118 Uiso 1 1 calc GR . . . .
H20B H 0.4835 0.3332 -0.3257 0.118 Uiso 1 1 calc GR . . . .
H20C H 0.3630 0.4862 -0.3191 0.118 Uiso 1 1 calc GR . . . .


_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
O14 C9 1.2177(16) . ?
N1 C9 1.3456(17) . ?
N1 C2 1.4093(18) . ?
N11 C10 1.4906(19) . ?
N11 O13 1.2090(18) . ?
N11 O12 1.2123(18) . ?
C10 C8 1.5274(18) . ?
C9 C8 1.5531(17) . ?
C8 C15 1.5730(18) . ?
C8 C7 1.5109(17) . ?
C16 N17 1.134(2) . ?
C16 C15 1.4721(19) . ?
C15 C18 1.4714(19) . ?
C18 N19 1.132(2) . ?
C2 C7 1.3847(19) . ?
C2 C3 1.377(2) . ?
C7 C6 1.3804(19) . ?
C6 C5 1.401(2) . ?
C5 C4 1.383(3) . ?
C5 C20 1.517(2) . ?
C3 C4 1.389(3) . ?

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
C9 N1 C2 112.22(11) . . ?
O13 N11 C10 119.38(12) . . ?
O13 N11 O12 124.20(15) . . ?
O12 N11 C10 116.42(14) . . ?
N11 C10 C8 113.04(11) . . ?
O14 C9 N1 127.82(13) . . ?
O14 C9 C8 124.81(12) . . ?
N1 C9 C8 107.20(11) . . ?
C10 C8 C9 113.11(11) . . ?
C10 C8 C15 106.14(10) . . ?
C9 C8 C15 104.84(10) . . ?
C7 C8 C10 116.99(11) . . ?
C7 C8 C9 102.26(10) . . ?
C7 C8 C15 112.98(11) . . ?
N17 C16 C15 178.34(16) . . ?
C16 C15 C8 111.42(10) . . ?
C18 C15 C8 112.30(11) . . ?
C18 C15 C16 108.75(12) . . ?
N19 C18 C15 179.31(19) . . ?
C7 C2 N1 109.70(11) . . ?
C3 C2 N1 128.83(14) . . ?
C3 C2 C7 121.46(14) . . ?
C2 C7 C8 108.24(11) . . ?
C6 C7 C8 130.93(13) . . ?
C6 C7 C2 120.81(13) . . ?
C7 C6 C5 118.87(15) . . ?
C6 C5 C20 119.36(18) . . ?
C4 C5 C6 118.87(15) . . ?
C4 C5 C20 121.76(16) . . ?
C2 C3 C4 117.20(15) . . ?
C5 C4 C3 122.71(14) . . ?

_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_gz050305
_database_code_depnum_ccdc_archive 'CCDC 1053772'
_audit_update_record             
;
2015-03-13 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;
_audit_creation_date             2015-03-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C17 H15 N3 O3)'
_chemical_formula_sum            'C34 H26 N6 O6'
_chemical_formula_weight         614.61
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 N1 O1'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.82662(14)
_cell_length_b                   27.6395(4)
_cell_length_c                   13.1668(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.9160(17)
_cell_angle_gamma                90
_cell_volume                     3089.08(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12705
_cell_measurement_temperature    288.02(10)
_cell_measurement_theta_max      71.2920
_cell_measurement_theta_min      4.7260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22707
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.498
_diffrn_reflns_theta_min         4.737
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      288.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   76.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703  -99.0000   30.0000 75

#__ type_ start__ end____ width___ exp.time_
  2 omega  -32.00   56.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703  -38.0000    0.0000 88

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   76.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703  -99.0000   90.0000 75

#__ type_ start__ end____ width___ exp.time_
  4 omega    1.00   27.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703   93.0000 -156.5327 26

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   27.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703   93.0000   14.0788 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   10.00  105.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703   77.0000 -150.0000 95

#__ type_ start__ end____ width___ exp.time_
  7 omega   10.00  105.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703   77.0000  -60.0000 95

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00  110.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000   90.0000 71

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00  116.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -112.0000  -90.0000 78

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   98.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
 13 omega   91.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
 14 omega   91.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 85

#__ type_ start__ end____ width___ exp.time_
 15 omega  101.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  112.0000 -180.0000 77

#__ type_ start__ end____ width___ exp.time_
 16 omega   40.00  135.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 95

#__ type_ start__ end____ width___ exp.time_
 17 omega   57.00  109.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703  178.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
 18 omega   18.00  106.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703   38.0000  120.0000 88

#__ type_ start__ end____ width___ exp.time_
 19 omega   18.00  106.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703   38.0000 -180.0000 88

#__ type_ start__ end____ width___ exp.time_
 20 omega   57.00  109.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703  178.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
 21 omega   18.00  106.00   1.0000    1.3100
omega____ theta____ kappa____ phi______ frames
    -       36.9703   38.0000   60.0000 88

#__ type_ start__ end____ width___ exp.time_
 22 omega   70.00  147.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -90.0000 77

#__ type_ start__ end____ width___ exp.time_
 23 omega   70.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0684500000
_diffrn_orient_matrix_UB_12      0.0511154000
_diffrn_orient_matrix_UB_13      -0.0024506000
_diffrn_orient_matrix_UB_21      0.1385551000
_diffrn_orient_matrix_UB_22      -0.0215413000
_diffrn_orient_matrix_UB_23      -0.0351201000
_diffrn_orient_matrix_UB_31      -0.0951987000
_diffrn_orient_matrix_UB_32      0.0054013000
_diffrn_orient_matrix_UB_33      -0.1164610000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5585
_reflns_number_total             5944
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         5944
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0639
_refine_ls_restrained_S_all      1.158
_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)+(0.0605P)²+2.5454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1699
_refine_ls_wR_factor_ref         0.1714
_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
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C6(H6), C5(H5), C28(H28), C29(H29), C31(H31), C30(H30)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C17(H17A,H17B,H17C), C44(H44A,H44B,
 H44C), C40(H40A,H40B,H40C), C46(H46A,H46B,H46C)
;
_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
O10 O 0.28177(19) 0.71656(6) 0.46037(16) 0.0467(4) Uani 1 1 d . . . . .
N20 N 0.0681(3) 0.76184(8) 0.4263(2) 0.0457(5) Uani 1 1 d . . . . .
C14 C 0.1235(3) 0.71784(8) 0.41660(18) 0.0359(5) Uani 1 1 d . . . . .
N1 N -0.0346(2) 0.55774(8) 0.34585(18) 0.0441(5) Uani 1 1 d . . . . .
O22 O 0.0317(3) 0.59093(8) 0.51203(17) 0.0617(6) Uani 1 1 d . . . . .
C2 C 0.0370(3) 0.58991(9) 0.4212(2) 0.0414(5) Uani 1 1 d . . . . .
C4 C 0.0855(3) 0.60929(9) 0.2570(2) 0.0428(6) Uani 1 1 d . . . . .
C13 C 0.0429(3) 0.67801(9) 0.3714(2) 0.0382(5) Uani 1 1 d . . . . .
O16 O 0.3188(3) 0.54863(8) 0.4257(2) 0.0700(6) Uani 1 1 d . . . . .
C9 C -0.0032(3) 0.56748(9) 0.2489(2) 0.0379(5) Uani 1 1 d . . . . .
C18 C -0.1209(3) 0.68269(9) 0.3261(2) 0.0495(7) Uani 1 1 d . . . . .
C12 C 0.2962(3) 0.63295(9) 0.4190(2) 0.0416(6) Uani 1 1 d . . . . .
C11 C 0.3649(3) 0.67437(9) 0.4597(2) 0.0414(5) Uani 1 1 d . . . . .
C3 C 0.1195(3) 0.62914(9) 0.36743(19) 0.0385(5) Uani 1 1 d . . . . .
C15 C 0.3846(3) 0.58688(11) 0.4201(2) 0.0542(7) Uani 1 1 d . . . . .
C8 C -0.0467(3) 0.54073(11) 0.1560(2) 0.0534(7) Uani 1 1 d . . . . .
H8 H -0.1026 0.5119 0.1512 0.064 Uiso 1 1 calc R . . . .
C21 C 0.5340(3) 0.68495(12) 0.5147(3) 0.0588(8) Uani 1 1 d . . . . .
H21A H 0.5914 0.6897 0.4632 0.088 Uiso 1 1 calc GR . . . .
H21B H 0.5786 0.6582 0.5597 0.088 Uiso 1 1 calc GR . . . .
H21C H 0.5405 0.7137 0.5566 0.088 Uiso 1 1 calc GR . . . .
N19 N -0.2540(3) 0.68619(11) 0.2901(3) 0.0793(10) Uani 1 1 d . . . . .
C7 C -0.0016(4) 0.55964(13) 0.0704(2) 0.0642(8) Uani 1 1 d . . . . .
H7 H -0.0299 0.5430 0.0065 0.077 Uiso 1 1 calc R . . . .
C6 C 0.0817(5) 0.60115(15) 0.0766(3) 0.0753(10) Uani 1 1 d . . . . .
H6 H 0.1091 0.6125 0.0175 0.090 Uiso 1 1 calc R . . . .
C23 C -0.1231(4) 0.51609(10) 0.3636(3) 0.0608(8) Uani 1 1 d . . . . .
H23A H -0.0632 0.4872 0.3621 0.091 Uiso 1 1 calc GR . . . .
H23B H -0.2210 0.5144 0.3093 0.091 Uiso 1 1 calc GR . . . .
H23C H -0.1438 0.5189 0.4312 0.091 Uiso 1 1 calc GR . . . .
C5 C 0.1273(4) 0.62738(13) 0.1722(2) 0.0629(8) Uani 1 1 d . . . . .
H5 H 0.1841 0.6561 0.1772 0.076 Uiso 1 1 calc R . . . .
C17 C 0.5496(5) 0.58628(16) 0.4125(5) 0.117(2) Uani 1 1 d . . . . .
H17A H 0.6209 0.5862 0.4821 0.175 Uiso 1 1 calc GR . . . .
H17B H 0.5681 0.6145 0.3750 0.175 Uiso 1 1 calc GR . . . .
H17C H 0.5663 0.5578 0.3753 0.175 Uiso 1 1 calc GR . . . .
O45 O 0.3329(2) 0.67223(6) -0.00200(13) 0.0404(4) Uani 1 1 d . . . . .
O33 O 0.20412(19) 0.72771(7) -0.31331(15) 0.0462(4) Uani 1 1 d . . . . .
O39 O 0.1586(2) 0.58011(7) -0.14690(15) 0.0505(5) Uani 1 1 d . . . . .
C37 C 0.3619(3) 0.72904(8) -0.26762(18) 0.0356(5) Uani 1 1 d . . . . .
C26 C 0.3527(2) 0.64825(8) -0.17962(17) 0.0312(5) Uani 1 1 d . . . . .
N24 N 0.4898(2) 0.60893(7) -0.02190(16) 0.0398(5) Uani 1 1 d . . . . .
N43 N 0.4239(3) 0.77012(8) -0.2926(2) 0.0473(5) Uani 1 1 d . . . . .
C35 C 0.1780(3) 0.65109(9) -0.23596(17) 0.0337(5) Uani 1 1 d . . . . .
C27 C 0.4346(3) 0.60265(8) -0.20204(19) 0.0347(5) Uani 1 1 d . . . . .
C28 C 0.4398(3) 0.58259(9) -0.2960(2) 0.0424(6) Uani 1 1 d . . . . .
H28 H 0.3846 0.5964 -0.3599 0.051 Uiso 1 1 calc R . . . .
C34 C 0.1157(3) 0.68872(9) -0.29708(18) 0.0383(5) Uani 1 1 d . . . . .
C41 C 0.6021(3) 0.69589(9) -0.1651(2) 0.0442(6) Uani 1 1 d . . . . .
C36 C 0.4365(3) 0.69281(8) -0.20487(18) 0.0337(5) Uani 1 1 d . . . . .
C38 C 0.0879(3) 0.60889(9) -0.21311(19) 0.0398(5) Uani 1 1 d . . . . .
C29 C 0.5302(3) 0.54082(10) -0.2937(2) 0.0507(7) Uani 1 1 d . . . . .
H29 H 0.5358 0.5267 -0.3567 0.061 Uiso 1 1 calc R . . . .
C32 C 0.5168(3) 0.58213(9) -0.1066(2) 0.0385(5) Uani 1 1 d . . . . .
C25 C 0.3855(3) 0.64495(8) -0.05755(18) 0.0331(5) Uani 1 1 d . . . . .
C31 C 0.6051(3) 0.54042(10) -0.1023(3) 0.0513(7) Uani 1 1 d . . . . .
H31 H 0.6581 0.5263 -0.0384 0.062 Uiso 1 1 calc R . . . .
C30 C 0.6107(3) 0.52062(10) -0.1991(3) 0.0547(7) Uani 1 1 d . . . . .
H30 H 0.6707 0.4930 -0.1993 0.066 Uiso 1 1 calc R . . . .
C44 C -0.0509(3) 0.69882(12) -0.3588(2) 0.0552(7) Uani 1 1 d . . . . .
H44A H -0.0580 0.7310 -0.3873 0.083 Uiso 1 1 calc GR . . . .
H44B H -0.1187 0.6960 -0.3132 0.083 Uiso 1 1 calc GR . . . .
H44C H -0.0828 0.6759 -0.4155 0.083 Uiso 1 1 calc GR . . . .
N42 N 0.7365(3) 0.69888(11) -0.1349(3) 0.0738(9) Uani 1 1 d . . . . .
C40 C -0.0826(3) 0.59966(13) -0.2669(3) 0.0614(8) Uani 1 1 d . . . . .
H40A H -0.1103 0.5677 -0.2498 0.092 Uiso 1 1 calc GR . . . .
H40B H -0.1004 0.6024 -0.3420 0.092 Uiso 1 1 calc GR . . . .
H40C H -0.1462 0.6230 -0.2435 0.092 Uiso 1 1 calc GR . . . .
C46 C 0.5525(4) 0.59712(12) 0.0891(2) 0.0629(8) Uani 1 1 d . . . . .
H46A H 0.5193 0.5652 0.1019 0.094 Uiso 1 1 calc GR . . . .
H46B H 0.5140 0.6200 0.1310 0.094 Uiso 1 1 calc GR . . . .
H46C H 0.6654 0.5984 0.1079 0.094 Uiso 1 1 calc GR . . . .
H43A H 0.525(5) 0.7768(13) -0.263(3) 0.068(10) Uiso 1 1 d . . . . .
H43B H 0.375(5) 0.7851(14) -0.348(3) 0.075(11) Uiso 1 1 d . . . . .
H20A H -0.031(4) 0.7683(11) 0.405(2) 0.049(8) Uiso 1 1 d . . . . .
H20B H 0.133(4) 0.7828(13) 0.446(3) 0.059(10) Uiso 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
O10 C14 1.357(3) . ?
O10 C11 1.379(3) . ?
N20 C14 1.330(3) . ?
C14 C13 1.356(3) . ?
N1 C2 1.353(3) . ?
N1 C9 1.404(3) . ?
N1 C23 1.446(3) . ?
O22 C2 1.210(3) . ?
C2 C3 1.579(3) . ?
C4 C9 1.384(3) . ?
C4 C3 1.505(3) . ?
C4 C5 1.363(4) . ?
C13 C18 1.411(3) . ?
C13 C3 1.518(3) . ?
O16 C15 1.218(4) . ?
C9 C8 1.390(4) . ?
C18 N19 1.144(4) . ?
C12 C11 1.337(4) . ?
C12 C3 1.524(3) . ?
C12 C15 1.492(4) . ?
C11 C21 1.499(3) . ?
C15 C17 1.487(5) . ?
C8 C7 1.397(5) . ?
C7 C6 1.353(5) . ?
C6 C5 1.413(4) . ?
O45 C25 1.227(3) . ?
O33 C37 1.358(3) . ?
O33 C34 1.381(3) . ?
O39 C38 1.218(3) . ?
C37 N43 1.340(3) . ?
C37 C36 1.349(3) . ?
C26 C35 1.519(3) . ?
C26 C27 1.521(3) . ?
C26 C36 1.520(3) . ?
C26 C25 1.556(3) . ?
N24 C32 1.412(3) . ?
N24 C25 1.350(3) . ?
N24 C46 1.451(3) . ?
C35 C34 1.337(3) . ?
C35 C38 1.488(3) . ?
C27 C28 1.368(3) . ?
C27 C32 1.388(3) . ?
C28 C29 1.399(4) . ?
C34 C44 1.499(3) . ?
C41 C36 1.414(3) . ?
C41 N42 1.146(3) . ?
C38 C40 1.499(4) . ?
C29 C30 1.373(4) . ?
C32 C31 1.384(3) . ?
C31 C30 1.400(4) . ?

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
C14 O10 C11 120.44(19) . . ?
N20 C14 O10 110.2(2) . . ?
N20 C14 C13 128.4(2) . . ?
C13 C14 O10 121.3(2) . . ?
C2 N1 C9 111.8(2) . . ?
C2 N1 C23 124.7(2) . . ?
C9 N1 C23 123.3(2) . . ?
N1 C2 C3 107.6(2) . . ?
O22 C2 N1 127.1(3) . . ?
O22 C2 C3 125.1(2) . . ?
C9 C4 C3 109.7(2) . . ?
C5 C4 C9 121.2(3) . . ?
C5 C4 C3 129.1(2) . . ?
C14 C13 C18 117.7(2) . . ?
C14 C13 C3 123.5(2) . . ?
C18 C13 C3 118.8(2) . . ?
C4 C9 N1 109.8(2) . . ?
C4 C9 C8 121.7(3) . . ?
C8 C9 N1 128.5(2) . . ?
N19 C18 C13 179.3(4) . . ?
C11 C12 C3 122.3(2) . . ?
C11 C12 C15 123.3(2) . . ?
C15 C12 C3 114.5(2) . . ?
O10 C11 C21 107.1(2) . . ?
C12 C11 O10 122.9(2) . . ?
C12 C11 C21 130.0(2) . . ?
C4 C3 C2 100.85(19) . . ?
C4 C3 C13 112.6(2) . . ?
C4 C3 C12 111.4(2) . . ?
C13 C3 C2 109.32(19) . . ?
C13 C3 C12 109.53(19) . . ?
C12 C3 C2 112.9(2) . . ?
O16 C15 C12 119.0(3) . . ?
O16 C15 C17 119.1(3) . . ?
C17 C15 C12 121.9(3) . . ?
C9 C8 C7 116.1(3) . . ?
C6 C7 C8 122.6(3) . . ?
C7 C6 C5 120.4(3) . . ?
C4 C5 C6 117.8(3) . . ?
C37 O33 C34 120.47(19) . . ?
N43 C37 O33 110.6(2) . . ?
N43 C37 C36 128.0(2) . . ?
C36 C37 O33 121.3(2) . . ?
C35 C26 C27 114.87(18) . . ?
C35 C26 C36 109.95(18) . . ?
C35 C26 C25 112.56(17) . . ?
C27 C26 C25 100.85(17) . . ?
C36 C26 C27 110.09(17) . . ?
C36 C26 C25 108.06(17) . . ?
C32 N24 C46 125.3(2) . . ?
C25 N24 C32 111.0(2) . . ?
C25 N24 C46 123.5(2) . . ?
C34 C35 C26 121.9(2) . . ?
C34 C35 C38 125.2(2) . . ?
C38 C35 C26 112.8(2) . . ?
C28 C27 C26 130.3(2) . . ?
C28 C27 C32 120.9(2) . . ?
C32 C27 C26 108.7(2) . . ?
C27 C28 C29 118.4(3) . . ?
O33 C34 C44 106.4(2) . . ?
C35 C34 O33 122.9(2) . . ?
C35 C34 C44 130.6(2) . . ?
N42 C41 C36 178.5(3) . . ?
C37 C36 C26 123.4(2) . . ?
C37 C36 C41 117.6(2) . . ?
C41 C36 C26 118.9(2) . . ?
O39 C38 C35 117.3(2) . . ?
O39 C38 C40 118.6(2) . . ?
C35 C38 C40 124.1(2) . . ?
C30 C29 C28 120.4(3) . . ?
C27 C32 N24 109.9(2) . . ?
C31 C32 N24 128.3(2) . . ?
C31 C32 C27 121.7(2) . . ?
O45 C25 C26 125.9(2) . . ?
O45 C25 N24 125.4(2) . . ?
N24 C25 C26 108.56(19) . . ?
C32 C31 C30 116.7(3) . . ?
C29 C30 C31 121.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
