# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_zchn52
_audit_block_doi                 10.5517/cc12q8sv
_database_code_depnum_ccdc_archive 'CCDC 1004517'
_audit_update_record             
;
2015-03-23 deposited with the CCDC.
2016-03-02 downloaded from the CCDC.
;
_audit_creation_date             2014-05-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H20 N4'
_chemical_formula_sum            'C23 H20 N4'
_chemical_formula_weight         352.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N4 C20 H20'
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'

_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 21/c'
_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                   15.2591(5)
_cell_length_b                   7.75811(18)
_cell_length_c                   16.2453(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.972(3)
_cell_angle_gamma                90
_cell_volume                     1848.91(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4397
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      67.4850
_cell_measurement_theta_min      5.6170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9804
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.421
_diffrn_reflns_theta_min         5.638
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0941034000
_diffrn_orient_matrix_UB_12      0.0793422000
_diffrn_orient_matrix_UB_13      -0.0427020000
_diffrn_orient_matrix_UB_21      0.0246982000
_diffrn_orient_matrix_UB_22      0.0115375000
_diffrn_orient_matrix_UB_23      -0.0856087000
_diffrn_orient_matrix_UB_31      -0.0395504000
_diffrn_orient_matrix_UB_32      -0.1816677000
_diffrn_orient_matrix_UB_33      -0.0240519000
_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              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2779
_reflns_number_total             3314
_reflns_odcompleteness_completeness 99.78
_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 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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         0.160
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0281(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0730P)²+0.1570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1237
_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:
 C5(H5), C9(H9), C10(H10), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21), C23(H23), C25(H25), C26(H26), C27(H27)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_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
N1 N 0.65776(7) 0.21607(14) 0.92298(7) 0.0526(3) Uani 1 1 d . . . . .
C2 C 0.66073(8) 0.33702(17) 0.86472(8) 0.0499(3) Uani 1 1 d . . . . .
C3 C 0.60069(8) 0.49005(18) 0.85941(8) 0.0523(3) Uani 1 1 d . . . . .
C4 C 0.83488(9) 0.16964(16) 0.75944(8) 0.0496(3) Uani 1 1 d . . . . .
C5 C 0.97940(9) 0.08936(18) 0.73612(9) 0.0584(4) Uani 1 1 d . . . . .
H5 H 1.0358 0.0361 0.7565 0.070 Uiso 1 1 calc R . . . .
C6 C 0.95671(9) 0.16676(16) 0.65510(8) 0.0518(3) Uani 1 1 d . . . . .
C7 C 0.71182(10) -0.04940(17) 0.99642(8) 0.0558(3) Uani 1 1 d . . . . .
C8 C 0.77357(8) 0.18204(16) 0.81548(8) 0.0498(3) Uani 1 1 d . . . . .
C9 C 0.91975(9) 0.09069(18) 0.78609(9) 0.0563(3) Uani 1 1 d . . . . .
H9 H 0.9368 0.0371 0.8393 0.068 Uiso 1 1 calc R . . . .
C10 C 0.71672(8) 0.32421(17) 0.81093(8) 0.0510(3) Uani 1 1 d . . . . .
H10 H 0.7164 0.4112 0.7715 0.061 Uiso 1 1 calc R . . . .
N11 N 1.01678(8) 0.17122(17) 0.60570(8) 0.0662(4) Uani 1 1 d . . . . .
C12 C 0.77102(9) 0.05843(17) 0.87667(8) 0.0542(3) Uani 1 1 d . . . . .
H12 H 0.8080 -0.0387 0.8828 0.065 Uiso 1 1 calc R . . . .
N13 N 0.61726(9) 0.62379(16) 0.81368(8) 0.0652(3) Uani 1 1 d . . . . .
C14 C 0.71330(9) 0.07968(17) 0.92875(8) 0.0519(3) Uani 1 1 d . . . . .
C15 C 0.64486(11) -0.04787(19) 1.03856(9) 0.0635(4) Uani 1 1 d . . . . .
H15 H 0.5975 0.0317 1.0237 0.076 Uiso 1 1 calc R . . . .
C16 C 0.53062(10) 0.4929(2) 0.89792(10) 0.0665(4) Uani 1 1 d . . . . .
H16 H 0.5207 0.3991 0.9299 0.080 Uiso 1 1 calc R . . . .
C17 C 0.81176(9) 0.24246(19) 0.67807(9) 0.0569(4) Uani 1 1 d . . . . .
H17 H 0.7549 0.2942 0.6576 0.068 Uiso 1 1 calc R . . . .
C18 C 0.87006(9) 0.24065(18) 0.62678(9) 0.0566(3) Uani 1 1 d . . . . .
H18 H 0.8515 0.2893 0.5724 0.068 Uiso 1 1 calc R . . . .
N19 N 0.78038(11) -0.16206(19) 1.01574(10) 0.0833(4) Uani 1 1 d . . . . .
C20 C 0.56402(12) 0.7627(2) 0.80734(10) 0.0722(4) Uani 1 1 d . . . . .
H20 H 0.5763 0.8574 0.7772 0.087 Uiso 1 1 calc R . . . .
C21 C 0.49234(12) 0.7733(2) 0.84270(10) 0.0745(5) Uani 1 1 d . . . . .
H21 H 0.4561 0.8715 0.8356 0.089 Uiso 1 1 calc R . . . .
C22 C 1.10787(10) 0.1067(2) 0.63910(11) 0.0712(4) Uani 1 1 d . . . . .
H22A H 1.1378 0.1684 0.6904 0.107 Uiso 1 1 calc GR . . . .
H22B H 1.1411 0.1223 0.5973 0.107 Uiso 1 1 calc GR . . . .
H22C H 1.1057 -0.0137 0.6520 0.107 Uiso 1 1 calc GR . . . .
C23 C 0.64881(14) -0.1654(2) 1.10289(11) 0.0786(5) Uani 1 1 d . . . . .
H23 H 0.6044 -0.1659 1.1323 0.094 Uiso 1 1 calc R . . . .
C24 C 0.99149(12) 0.2486(2) 0.52237(10) 0.0726(4) Uani 1 1 d . . . . .
H24A H 0.9417 0.1856 0.4858 0.109 Uiso 1 1 calc GR . . . .
H24B H 1.0426 0.2462 0.4987 0.109 Uiso 1 1 calc GR . . . .
H24C H 0.9733 0.3659 0.5269 0.109 Uiso 1 1 calc GR . . . .
C25 C 0.78185(17) -0.2752(3) 1.07783(15) 0.1040(7) Uani 1 1 d . . . . .
H25 H 0.8290 -0.3553 1.0913 0.125 Uiso 1 1 calc R . . . .
C26 C 0.71845(16) -0.2809(2) 1.12299(13) 0.0906(6) Uani 1 1 d . . . . .
H26 H 0.7228 -0.3616 1.1663 0.109 Uiso 1 1 calc R . . . .
C27 C 0.47552(12) 0.6363(3) 0.88849(11) 0.0789(5) Uani 1 1 d . . . . .
H27 H 0.4273 0.6395 0.9132 0.095 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3423(17) . ?
N1 C14 1.3427(18) . ?
C2 C3 1.4876(19) . ?
C2 C10 1.3836(18) . ?
C3 N13 1.3401(18) . ?
C3 C16 1.3795(18) . ?
C4 C8 1.4772(17) . ?
C4 C9 1.3897(18) . ?
C4 C17 1.3908(19) . ?
C5 C6 1.4007(19) . ?
C5 C9 1.3763(18) . ?
C6 N11 1.3748(17) . ?
C6 C18 1.3978(19) . ?
C7 C14 1.4917(18) . ?
C7 C15 1.3777(19) . ?
C7 N19 1.3328(19) . ?
C8 C10 1.3926(18) . ?
C8 C12 1.3894(18) . ?
N11 C22 1.4358(19) . ?
N11 C24 1.4334(19) . ?
C12 C14 1.3889(18) . ?
N13 C20 1.3362(19) . ?
C15 C23 1.376(2) . ?
C16 C27 1.378(2) . ?
C17 C18 1.3762(19) . ?
N19 C25 1.333(2) . ?
C20 C21 1.371(2) . ?
C21 C27 1.361(3) . ?
C23 C26 1.359(3) . ?
C25 C26 1.366(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
C2 N1 C14 117.19(11) . . ?
N1 C2 C3 117.33(11) . . ?
N1 C2 C10 122.79(12) . . ?
C10 C2 C3 119.88(12) . . ?
N13 C3 C2 116.29(11) . . ?
N13 C3 C16 121.82(13) . . ?
C16 C3 C2 121.88(13) . . ?
C9 C4 C8 122.05(12) . . ?
C9 C4 C17 116.49(12) . . ?
C17 C4 C8 121.42(11) . . ?
C9 C5 C6 121.22(12) . . ?
N11 C6 C5 121.81(12) . . ?
N11 C6 C18 121.32(12) . . ?
C18 C6 C5 116.87(12) . . ?
C15 C7 C14 121.61(13) . . ?
N19 C7 C14 116.35(12) . . ?
N19 C7 C15 122.01(13) . . ?
C10 C8 C4 120.65(11) . . ?
C12 C8 C4 122.90(11) . . ?
C12 C8 C10 116.42(12) . . ?
C5 C9 C4 122.04(12) . . ?
C2 C10 C8 120.48(12) . . ?
C6 N11 C22 120.15(12) . . ?
C6 N11 C24 120.82(12) . . ?
C24 N11 C22 118.94(12) . . ?
C14 C12 C8 120.08(12) . . ?
C20 N13 C3 117.62(13) . . ?
N1 C14 C7 116.31(11) . . ?
N1 C14 C12 123.02(12) . . ?
C12 C14 C7 120.66(12) . . ?
C23 C15 C7 119.23(15) . . ?
C27 C16 C3 119.20(15) . . ?
C18 C17 C4 122.29(12) . . ?
C17 C18 C6 121.02(12) . . ?
C7 N19 C25 117.32(15) . . ?
N13 C20 C21 123.67(16) . . ?
C27 C21 C20 118.32(15) . . ?
C26 C23 C15 119.17(16) . . ?
N19 C25 C26 124.11(18) . . ?
C23 C26 C25 118.15(16) . . ?
C21 C27 C16 119.35(15) . . ?

####################################################################### 
# 
# 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_skm67
_audit_block_doi                 10.5517/cc12z62b
_database_code_depnum_ccdc_archive 'CCDC 1012121'
_audit_update_record             
;
2014-07-03 deposited with the CCDC.
2016-03-02 downloaded from the CCDC.
;
_audit_creation_date             2014-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H19 N3 O'
_chemical_formula_sum            'C26 H19 N3 O'
_chemical_formula_weight         389.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      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                   12.4993(4)
_cell_length_b                   12.6093(5)
_cell_length_c                   13.1403(5)
_cell_angle_alpha                102.843(3)
_cell_angle_beta                 90.295(3)
_cell_angle_gamma                94.809(3)
_cell_volume                     2011.47(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9096
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      67.2310
_cell_measurement_theta_min      3.4460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24760
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.591
_diffrn_reflns_theta_min         3.451
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -31.00   70.00   1.0000    5.2850
omega____ theta____ kappa____ phi______ frames
    -       41.3844  -57.0000  -60.0000 101

#__ type_ start__ end____ width___ exp.time_
  2 omega   -3.00   95.00   1.0000    5.2850
omega____ theta____ kappa____ phi______ frames
    -       41.3844 -125.0000 -120.0000 98

#__ type_ start__ end____ width___ exp.time_
  3 omega   13.00  115.00   1.0000    5.2850
omega____ theta____ kappa____ phi______ frames
    -       41.3844   57.0000   90.0000 102

#__ type_ start__ end____ width___ exp.time_
  4 omega    9.00  131.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -93.0000 -172.0221 122

#__ type_ start__ end____ width___ exp.time_
  5 omega    9.00  131.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -93.0000  -26.2748 122

#__ type_ start__ end____ width___ exp.time_
  6 omega    9.00  131.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -93.0000  -85.1921 122

#__ type_ start__ end____ width___ exp.time_
  7 omega    9.00  130.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -90.0000 -120.1524 121

#__ type_ start__ end____ width___ exp.time_
  8 omega    9.00  130.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -91.0000  132.2804 121

#__ type_ start__ end____ width___ exp.time_
  9 omega   23.00  109.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -86.0000    2.3799 86

#__ type_ start__ end____ width___ exp.time_
 10 omega   69.00  111.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000   60.0000 42

#__ type_ start__ end____ width___ exp.time_
 11 omega  114.00  162.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000   60.0000 48

#__ type_ start__ end____ width___ exp.time_
 12 omega  123.00  149.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   16.00   57.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000   60.0000 41

#__ type_ start__ end____ width___ exp.time_
 14 omega   63.00  116.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 15 omega   26.00   55.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
 16 omega  124.00  158.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
 17 omega   21.00   65.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000   90.0000 44

#__ type_ start__ end____ width___ exp.time_
 18 omega   64.00   90.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega  113.00  173.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000   15.0000   30.0000 60

#__ type_ start__ end____ width___ exp.time_
 20 omega   50.00  102.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000  120.0000 52

#__ type_ start__ end____ width___ exp.time_
 21 omega   22.00  111.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -61.0000 -120.0000 89

#__ type_ start__ end____ width___ exp.time_
 22 omega   53.00   84.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -95.0000   60.0000 31

#__ type_ start__ end____ width___ exp.time_
 23 omega   76.00  103.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000   61.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 24 omega   40.00   66.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -30.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   42.00   68.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   69.00  101.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
 27 omega  121.00  165.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000   30.0000  -30.0000 44

#__ type_ start__ end____ width___ exp.time_
 28 omega   63.00   91.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -77.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
 29 omega   38.00  101.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -92.0000   86.7164 63

#__ type_ start__ end____ width___ exp.time_
 30 omega  153.00  178.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000    0.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 31 omega   52.00   54.00   1.0000   21.1350
omega____ theta____ kappa____ phi______ frames
    -       92.5000  -45.0000 -120.0000 2
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0044259000
_diffrn_orient_matrix_UB_12      -0.0457558000
_diffrn_orient_matrix_UB_13      -0.1186576000
_diffrn_orient_matrix_UB_21      -0.1021010000
_diffrn_orient_matrix_UB_22      -0.0761174000
_diffrn_orient_matrix_UB_23      0.0044126000
_diffrn_orient_matrix_UB_31      -0.0697396000
_diffrn_orient_matrix_UB_32      0.0890835000
_diffrn_orient_matrix_UB_33      -0.0192131000
_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              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5524
_reflns_number_total             7199
_reflns_odcompleteness_completeness 99.79
_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 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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         0.271
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         7199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      1.044
_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)+(0.0930P)²+0.0150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1803
_refine_ls_wR_factor_ref         0.2018
_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:
 C28(H28), C30(H30), C33(H33), C34(H34), C35(H35), C36(H36), C38(H38),
 C39(H39), C40(H40), C41(H41), C43(H43), C44(H44), C47(H47), C48(H48), C49(H49),
  C50(H50), C2(H2), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12),
 C13(H13), C14(H14), C15(H15), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23),
  C24(H24)
2.b Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C26(H26A,H26B,H26C)
;
_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
O3 O 0.06186(10) 0.69434(12) 0.03963(11) 0.0618(4) Uani 1 1 d . . . . .
N4 N 0.74129(12) 0.74272(11) 0.03368(11) 0.0456(3) Uani 1 1 d . . . . .
N5 N 0.70003(16) 0.89340(14) 0.29460(13) 0.0646(5) Uani 1 1 d . . . . .
N6 N 0.68758(14) 0.56890(13) -0.22186(12) 0.0582(4) Uani 1 1 d . . . . .
C27 C 0.68742(14) 0.79318(13) 0.11567(13) 0.0458(4) Uani 1 1 d . . . . .
C28 C 0.57612(15) 0.78809(14) 0.11736(14) 0.0495(4) Uani 1 1 d . . . . .
H28 H 0.5419 0.8236 0.1763 0.059 Uiso 1 1 calc R . . . .
C29 C 0.51610(14) 0.72958(14) 0.03054(14) 0.0470(4) Uani 1 1 d . . . . .
C30 C 0.57255(14) 0.67840(14) -0.05491(14) 0.0473(4) Uani 1 1 d . . . . .
H30 H 0.5356 0.6393 -0.1150 0.057 Uiso 1 1 calc R . . . .
C31 C 0.68342(14) 0.68574(13) -0.05048(13) 0.0434(4) Uani 1 1 d . . . . .
C32 C 0.75388(16) 0.85510(13) 0.20820(14) 0.0501(4) Uani 1 1 d . . . . .
C33 C 0.86404(17) 0.87135(15) 0.20304(17) 0.0596(5) Uani 1 1 d . . . . .
H33 H 0.8989 0.8451 0.1413 0.072 Uiso 1 1 calc R . . . .
C34 C 0.9219(2) 0.92774(16) 0.2921(2) 0.0722(6) Uani 1 1 d . . . . .
H34 H 0.9963 0.9399 0.2909 0.087 Uiso 1 1 calc R . . . .
C35 C 0.8682(2) 0.96501(18) 0.3812(2) 0.0782(7) Uani 1 1 d . . . . .
H35 H 0.9052 1.0017 0.4421 0.094 Uiso 1 1 calc R . . . .
C36 C 0.7589(2) 0.94733(19) 0.37910(18) 0.0774(7) Uani 1 1 d . . . . .
H36 H 0.7229 0.9743 0.4399 0.093 Uiso 1 1 calc R . . . .
C37 C 0.74598(14) 0.63068(13) -0.14058(13) 0.0459(4) Uani 1 1 d . . . . .
C38 C 0.85658(16) 0.64365(16) -0.14012(15) 0.0539(4) Uani 1 1 d . . . . .
H38 H 0.8946 0.6864 -0.0823 0.065 Uiso 1 1 calc R . . . .
C39 C 0.91046(18) 0.59248(18) -0.22635(17) 0.0650(5) Uani 1 1 d . . . . .
H39 H 0.9851 0.5993 -0.2271 0.078 Uiso 1 1 calc R . . . .
C40 C 0.8516(2) 0.53133(18) -0.31089(17) 0.0683(6) Uani 1 1 d . . . . .
H40 H 0.8852 0.4976 -0.3710 0.082 Uiso 1 1 calc R . . . .
C41 C 0.7418(2) 0.52140(18) -0.30404(17) 0.0685(6) Uani 1 1 d . . . . .
H41 H 0.7024 0.4784 -0.3609 0.082 Uiso 1 1 calc R . . . .
C42 C 0.39660(14) 0.71982(14) 0.03155(13) 0.0465(4) Uani 1 1 d . . . . .
C43 C 0.34419(15) 0.66500(16) 0.09766(15) 0.0555(5) Uani 1 1 d . . . . .
H43 H 0.3845 0.6339 0.1412 0.067 Uiso 1 1 calc R . . . .
C44 C 0.23226(16) 0.65363(16) 0.10263(15) 0.0563(5) Uani 1 1 d . . . . .
H44 H 0.1995 0.6147 0.1481 0.068 Uiso 1 1 calc R . . . .
C45 C 0.17085(14) 0.69999(14) 0.04046(14) 0.0479(4) Uani 1 1 d . . . . .
C46 C 0.22084(14) 0.75841(13) -0.03026(13) 0.0444(4) Uani 1 1 d . . . . .
C47 C 0.16031(16) 0.80821(15) -0.09550(15) 0.0532(4) Uani 1 1 d . . . . .
H47 H 0.0857 0.8021 -0.0932 0.064 Uiso 1 1 calc R . . . .
C48 C 0.21009(18) 0.86476(16) -0.16136(16) 0.0614(5) Uani 1 1 d . . . . .
H48 H 0.1692 0.8968 -0.2036 0.074 Uiso 1 1 calc R . . . .
C49 C 0.32173(19) 0.87506(17) -0.16606(16) 0.0637(5) Uani 1 1 d . . . . .
H49 H 0.3550 0.9140 -0.2112 0.076 Uiso 1 1 calc R . . . .
C50 C 0.38233(16) 0.82802(15) -0.10441(15) 0.0542(4) Uani 1 1 d . . . . .
H50 H 0.4568 0.8356 -0.1082 0.065 Uiso 1 1 calc R . . . .
C51 C 0.33465(14) 0.76829(12) -0.03508(13) 0.0436(4) Uani 1 1 d . . . . .
C52 C 0.00757(17) 0.63826(19) 0.10891(19) 0.0694(6) Uani 1 1 d . . . . .
H52A H 0.0220 0.5628 0.0915 0.104 Uiso 1 1 calc GR . . . .
H52B H -0.0683 0.6435 0.1031 0.104 Uiso 1 1 calc GR . . . .
H52C H 0.0322 0.6704 0.1792 0.104 Uiso 1 1 calc GR . . . .
O10 O -0.46923(11) 0.30744(12) 0.45199(12) 0.0667(4) Uani 1 1 d . . . . .
N1 N 0.20198(12) 0.26155(11) 0.46981(12) 0.0479(4) Uani 1 1 d . . . . .
N2 N 0.18026(14) 0.42758(13) 0.72812(13) 0.0596(4) Uani 1 1 d . . . . .
N3 N 0.13132(18) 0.11415(15) 0.20744(14) 0.0744(5) Uani 1 1 d . . . . .
C1 C 0.15501(14) 0.31717(13) 0.55427(13) 0.0455(4) Uani 1 1 d . . . . .
C2 C 0.04523(14) 0.32695(14) 0.55830(14) 0.0482(4) Uani 1 1 d . . . . .
H2 H 0.0155 0.3650 0.6189 0.058 Uiso 1 1 calc R . . . .
C3 C -0.02020(15) 0.27947(13) 0.47117(14) 0.0477(4) Uani 1 1 d . . . . .
C4 C 0.02943(16) 0.22272(14) 0.38399(15) 0.0505(4) Uani 1 1 d . . . . .
H4 H -0.0111 0.1902 0.3239 0.061 Uiso 1 1 calc R . . . .
C5 C 0.13888(15) 0.21448(13) 0.38614(14) 0.0477(4) Uani 1 1 d . . . . .
C6 C 0.22714(15) 0.36882(13) 0.64592(14) 0.0476(4) Uani 1 1 d . . . . .
C7 C 0.33597(16) 0.35601(16) 0.64426(16) 0.0565(5) Uani 1 1 d . . . . .
H7 H 0.3661 0.3154 0.5852 0.068 Uiso 1 1 calc R . . . .
C8 C 0.39921(19) 0.40421(18) 0.73114(19) 0.0683(6) Uani 1 1 d . . . . .
H8 H 0.4727 0.3971 0.7315 0.082 Uiso 1 1 calc R . . . .
C9 C 0.3520(2) 0.46256(19) 0.81659(19) 0.0720(6) Uani 1 1 d . . . . .
H9 H 0.3924 0.4947 0.8769 0.086 Uiso 1 1 calc R . . . .
C10 C 0.2441(2) 0.47278(18) 0.81178(17) 0.0693(6) Uani 1 1 d . . . . .
H10 H 0.2129 0.5136 0.8701 0.083 Uiso 1 1 calc R . . . .
C11 C 0.19363(17) 0.15303(14) 0.29362(15) 0.0546(5) Uani 1 1 d . . . . .
C12 C 0.30117(19) 0.13730(16) 0.29703(19) 0.0660(6) Uani 1 1 d . . . . .
H12 H 0.3420 0.1632 0.3582 0.079 Uiso 1 1 calc R . . . .
C13 C 0.3472(2) 0.08181(18) 0.2070(2) 0.0826(8) Uani 1 1 d . . . . .
H13 H 0.4198 0.0709 0.2069 0.099 Uiso 1 1 calc R . . . .
C14 C 0.2848(3) 0.04326(19) 0.1183(2) 0.0898(9) Uani 1 1 d . . . . .
H14 H 0.3139 0.0060 0.0570 0.108 Uiso 1 1 calc R . . . .
C15 C 0.1793(3) 0.0612(2) 0.1228(2) 0.0914(9) Uani 1 1 d . . . . .
H15 H 0.1371 0.0347 0.0625 0.110 Uiso 1 1 calc R . . . .
C16 C -0.13824(15) 0.28869(13) 0.46916(13) 0.0471(4) Uani 1 1 d . . . . .
C17 C -0.18140(16) 0.34252(16) 0.40085(15) 0.0554(5) Uani 1 1 d . . . . .
H17 H -0.1356 0.3739 0.3580 0.066 Uiso 1 1 calc R . . . .
C18 C -0.29168(16) 0.35177(16) 0.39336(15) 0.0562(5) Uani 1 1 d . . . . .
H18 H -0.3178 0.3906 0.3475 0.067 Uiso 1 1 calc R . . . .
C19 C -0.36104(15) 0.30401(14) 0.45317(14) 0.0503(4) Uani 1 1 d . . . . .
C20 C -0.32115(15) 0.24506(13) 0.52454(14) 0.0475(4) Uani 1 1 d . . . . .
C21 C -0.39077(17) 0.19299(16) 0.58581(17) 0.0602(5) Uani 1 1 d . . . . .
H21 H -0.4645 0.1958 0.5793 0.072 Uiso 1 1 calc R . . . .
C22 C -0.35142(19) 0.13835(18) 0.65475(18) 0.0695(6) Uani 1 1 d . . . . .
H22 H -0.3983 0.1042 0.6947 0.083 Uiso 1 1 calc R . . . .
C23 C -0.24064(19) 0.13387(17) 0.66521(16) 0.0655(5) Uani 1 1 d . . . . .
H23 H -0.2141 0.0972 0.7127 0.079 Uiso 1 1 calc R . . . .
C24 C -0.17156(16) 0.18234(15) 0.60692(14) 0.0526(4) Uani 1 1 d . . . . .
H24 H -0.0982 0.1782 0.6150 0.063 Uiso 1 1 calc R . . . .
C25 C -0.20875(14) 0.23946(13) 0.53366(13) 0.0454(4) Uani 1 1 d . . . . .
C26 C -0.51464(19) 0.3670(2) 0.3851(2) 0.0762(7) Uani 1 1 d . . . . .
H26A H -0.4960 0.3374 0.3143 0.114 Uiso 1 1 calc GR . . . .
H26B H -0.4872 0.4423 0.4051 0.114 Uiso 1 1 calc GR . . . .
H26C H -0.5914 0.3614 0.3907 0.114 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
O3 C45 1.358(2) . ?
O3 C52 1.415(2) . ?
N4 C27 1.339(2) . ?
N4 C31 1.347(2) . ?
N5 C32 1.339(3) . ?
N5 C36 1.345(3) . ?
N6 C37 1.344(2) . ?
N6 C41 1.331(3) . ?
C27 C28 1.388(3) . ?
C27 C32 1.496(3) . ?
C28 C29 1.390(3) . ?
C29 C30 1.392(2) . ?
C29 C42 1.489(2) . ?
C30 C31 1.381(2) . ?
C31 C37 1.493(2) . ?
C32 C33 1.379(3) . ?
C33 C34 1.390(3) . ?
C34 C35 1.364(4) . ?
C35 C36 1.364(4) . ?
C37 C38 1.378(3) . ?
C38 C39 1.382(3) . ?
C39 C40 1.373(3) . ?
C40 C41 1.374(4) . ?
C42 C43 1.363(3) . ?
C42 C51 1.432(2) . ?
C43 C44 1.398(3) . ?
C44 C45 1.371(2) . ?
C45 C46 1.425(3) . ?
C46 C47 1.419(2) . ?
C46 C51 1.421(2) . ?
C47 C48 1.360(3) . ?
C48 C49 1.394(3) . ?
C49 C50 1.365(3) . ?
C50 C51 1.410(2) . ?
O10 C19 1.357(2) . ?
O10 C26 1.420(2) . ?
N1 C1 1.341(2) . ?
N1 C5 1.344(2) . ?
N2 C6 1.335(2) . ?
N2 C10 1.344(3) . ?
N3 C11 1.345(3) . ?
N3 C15 1.336(3) . ?
C1 C2 1.388(2) . ?
C1 C6 1.493(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.388(2) . ?
C3 C16 1.490(2) . ?
C4 C5 1.381(3) . ?
C5 C11 1.492(2) . ?
C6 C7 1.383(3) . ?
C7 C8 1.378(3) . ?
C8 C9 1.365(4) . ?
C9 C10 1.368(4) . ?
C11 C12 1.377(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.370(4) . ?
C14 C15 1.357(5) . ?
C16 C17 1.373(2) . ?
C16 C25 1.425(3) . ?
C17 C18 1.398(3) . ?
C18 C19 1.365(3) . ?
C19 C20 1.431(2) . ?
C20 C21 1.408(3) . ?
C20 C25 1.418(2) . ?
C21 C22 1.366(3) . ?
C22 C23 1.398(3) . ?
C23 C24 1.354(3) . ?
C24 C25 1.422(2) . ?

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
C45 O3 C52 117.90(14) . . ?
C27 N4 C31 117.57(15) . . ?
C32 N5 C36 116.8(2) . . ?
C41 N6 C37 116.69(18) . . ?
N4 C27 C28 122.94(16) . . ?
N4 C27 C32 116.31(15) . . ?
C28 C27 C32 120.74(16) . . ?
C27 C28 C29 119.66(16) . . ?
C28 C29 C30 117.14(16) . . ?
C28 C29 C42 120.75(15) . . ?
C30 C29 C42 122.07(16) . . ?
C31 C30 C29 120.01(16) . . ?
N4 C31 C30 122.66(15) . . ?
N4 C31 C37 116.19(15) . . ?
C30 C31 C37 121.14(16) . . ?
N5 C32 C27 116.08(17) . . ?
N5 C32 C33 122.83(18) . . ?
C33 C32 C27 121.09(17) . . ?
C32 C33 C34 118.6(2) . . ?
C35 C34 C33 119.1(2) . . ?
C36 C35 C34 118.6(2) . . ?
N5 C36 C35 124.1(2) . . ?
N6 C37 C31 115.78(16) . . ?
N6 C37 C38 122.49(16) . . ?
C38 C37 C31 121.73(16) . . ?
C37 C38 C39 119.38(19) . . ?
C40 C39 C38 118.7(2) . . ?
C39 C40 C41 118.05(18) . . ?
N6 C41 C40 124.7(2) . . ?
C43 C42 C29 119.99(15) . . ?
C43 C42 C51 118.76(16) . . ?
C51 C42 C29 121.25(15) . . ?
C42 C43 C44 122.64(16) . . ?
C45 C44 C43 119.92(17) . . ?
O3 C45 C44 124.62(16) . . ?
O3 C45 C46 115.25(14) . . ?
C44 C45 C46 120.13(16) . . ?
C47 C46 C45 121.94(16) . . ?
C47 C46 C51 118.83(16) . . ?
C51 C46 C45 119.23(14) . . ?
C48 C47 C46 120.77(18) . . ?
C47 C48 C49 120.62(17) . . ?
C50 C49 C48 120.09(18) . . ?
C49 C50 C51 121.51(18) . . ?
C46 C51 C42 119.31(15) . . ?
C50 C51 C42 122.49(16) . . ?
C50 C51 C46 118.18(15) . . ?
C19 O10 C26 118.03(16) . . ?
C1 N1 C5 117.69(15) . . ?
C6 N2 C10 116.53(18) . . ?
C15 N3 C11 116.8(2) . . ?
N1 C1 C2 122.74(17) . . ?
N1 C1 C6 116.50(15) . . ?
C2 C1 C6 120.76(15) . . ?
C1 C2 C3 119.68(15) . . ?
C2 C3 C16 122.59(15) . . ?
C4 C3 C2 117.03(16) . . ?
C4 C3 C16 120.38(16) . . ?
C5 C4 C3 120.19(17) . . ?
N1 C5 C4 122.64(15) . . ?
N1 C5 C11 116.32(16) . . ?
C4 C5 C11 121.04(17) . . ?
N2 C6 C1 116.03(16) . . ?
N2 C6 C7 122.72(18) . . ?
C7 C6 C1 121.25(16) . . ?
C8 C7 C6 119.20(19) . . ?
C9 C8 C7 118.7(2) . . ?
C8 C9 C10 118.6(2) . . ?
N2 C10 C9 124.1(2) . . ?
N3 C11 C5 115.78(18) . . ?
N3 C11 C12 122.49(18) . . ?
C12 C11 C5 121.73(19) . . ?
C11 C12 C13 118.4(2) . . ?
C14 C13 C12 119.6(3) . . ?
C15 C14 C13 117.8(2) . . ?
N3 C15 C14 124.9(3) . . ?
C17 C16 C3 119.52(16) . . ?
C17 C16 C25 118.65(16) . . ?
C25 C16 C3 121.78(15) . . ?
C16 C17 C18 122.34(17) . . ?
C19 C18 C17 120.14(16) . . ?
O10 C19 C18 125.11(16) . . ?
O10 C19 C20 114.72(16) . . ?
C18 C19 C20 120.17(16) . . ?
C21 C20 C19 121.55(17) . . ?
C21 C20 C25 119.47(16) . . ?
C25 C20 C19 118.97(16) . . ?
C22 C21 C20 120.90(19) . . ?
C21 C22 C23 119.91(19) . . ?
C24 C23 C22 120.68(18) . . ?
C23 C24 C25 121.44(18) . . ?
C20 C25 C16 119.68(15) . . ?
C20 C25 C24 117.59(16) . . ?
C24 C25 C16 122.72(16) . . ?

_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_skm45
_audit_block_doi                 10.5517/cc139f94
_database_code_depnum_ccdc_archive 'CCDC 1021955'
_audit_update_record             
;
2014-08-29 deposited with the CCDC.
2016-03-02 downloaded from the CCDC.
;
_audit_creation_date             2014-08-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H14 N4'
_chemical_formula_sum            'C20 H14 N4'
_chemical_formula_weight         310.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N4 C20 H20'
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'

_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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   11.1295(8)
_cell_length_b                   11.4081(10)
_cell_length_c                   12.1912(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1547.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2003
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.3750
_cell_measurement_theta_min      4.1780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6805
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.035
_diffrn_reflns_theta_min         3.572
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -77.00  -32.00   1.0000   23.9800
omega____ theta____ kappa____ phi______ frames
    -       10.2152  179.0000 -120.0000 45

#__ type_ start__ end____ width___ exp.time_
  2 omega   -4.00   48.00   1.0000   23.9800
omega____ theta____ kappa____ phi______ frames
    -       10.2152  -99.0000   60.0000 52

#__ type_ start__ end____ width___ exp.time_
  3 omega  -86.00   30.00   1.0000   23.9800
omega____ theta____ kappa____ phi______ frames
    -      -11.1527  -19.0000 -120.0000 116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0148271000
_diffrn_orient_matrix_UB_12      -0.0600013000
_diffrn_orient_matrix_UB_13      -0.0065865000
_diffrn_orient_matrix_UB_21      -0.0619416000
_diffrn_orient_matrix_UB_22      0.0146531000
_diffrn_orient_matrix_UB_23      -0.0007070000
_diffrn_orient_matrix_UB_31      0.0024497000
_diffrn_orient_matrix_UB_32      0.0066784000
_diffrn_orient_matrix_UB_33      -0.0578441000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_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                1028
_reflns_number_total             1368
_reflns_odcompleteness_completeness 99.56
_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 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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    ?
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1368
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.011
_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)+(0.0612P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1038
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0000 -0.09944(14) 0.2500 0.0381(4) Uani 1 2 d S T P . .
N2 N 0.18685(11) -0.05172(11) 0.48546(10) 0.0467(4) Uani 1 1 d . . . . .
N3 N 0.0000 0.52246(16) 0.2500 0.0520(5) Uani 1 2 d S T P . .
C1 C 0.05494(11) -0.03907(12) 0.33001(11) 0.0353(4) Uani 1 1 d . . . . .
C2 C 0.05698(12) 0.08258(13) 0.33259(11) 0.0366(4) Uani 1 1 d . . . . .
H2 H 0.0962 0.1217 0.3892 0.044 Uiso 1 1 calc R . . . .
C3 C 0.0000 0.14547(18) 0.2500 0.0349(5) Uani 1 2 d S T P . .
C4 C 0.11518(12) -0.10989(13) 0.41645(11) 0.0363(4) Uani 1 1 d . . . . .
C5 C 0.09970(13) -0.23034(13) 0.42253(12) 0.0450(4) Uani 1 1 d . . . . .
H5 H 0.0481 -0.2687 0.3745 0.054 Uiso 1 1 calc R . . . .
C6 C 0.16219(14) -0.29213(14) 0.50110(12) 0.0529(5) Uani 1 1 d . . . . .
H6 H 0.1528 -0.3729 0.5070 0.063 Uiso 1 1 calc R . . . .
C7 C 0.23812(14) -0.23377(16) 0.57025(12) 0.0546(5) Uani 1 1 d . . . . .
H7 H 0.2829 -0.2740 0.6225 0.066 Uiso 1 1 calc R . . . .
C8 C 0.24643(15) -0.11461(16) 0.56045(12) 0.0549(5) Uani 1 1 d . . . . .
H8 H 0.2965 -0.0749 0.6089 0.066 Uiso 1 1 calc R . . . .
C9 C 0.0000 0.27606(17) 0.2500 0.0342(5) Uani 1 2 d S T P . .
C10 C -0.09003(13) 0.34017(13) 0.19961(11) 0.0418(4) Uani 1 1 d . . . . .
H10 H -0.1527 0.3019 0.1641 0.050 Uiso 1 1 calc R . . . .
C11 C -0.08653(14) 0.46024(14) 0.20215(13) 0.0492(4) Uani 1 1 d . . . . .
H11 H -0.1487 0.5009 0.1682 0.059 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3415(16) 4 ?
N1 C1 1.3415(16) . ?
N2 C4 1.3358(18) . ?
N2 C8 1.3381(19) . ?
N3 C11 1.3309(18) . ?
N3 C11 1.3309(18) 4 ?
C1 C2 1.388(2) . ?
C1 C4 1.4875(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.3895(17) . ?
C3 C2 1.3894(17) 4 ?
C3 C9 1.490(3) . ?
C4 C5 1.387(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.367(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.368(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.3843(17) 4 ?
C9 C10 1.3843(17) . ?
C10 H10 0.9300 . ?
C10 C11 1.371(2) . ?
C11 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C1 118.22(17) 4 . ?
C4 N2 C8 117.37(14) . . ?
C11 N3 C11 115.55(19) . 4 ?
N1 C1 C2 122.49(13) . . ?
N1 C1 C4 116.21(13) . . ?
C2 C1 C4 121.30(13) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.49(13) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C2 117.83(19) 4 . ?
C2 C3 C9 121.09(9) . . ?
C2 C3 C9 121.09(9) 4 . ?
N2 C4 C1 116.45(13) . . ?
N2 C4 C5 122.19(13) . . ?
C5 C4 C1 121.33(13) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.78(15) . . ?
C6 C5 H5 120.6 . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.45(16) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 120.9 . . ?
C6 C7 C8 118.17(15) . . ?
C8 C7 H7 120.9 . . ?
N2 C8 C7 124.00(16) . . ?
N2 C8 H8 118.0 . . ?
C7 C8 H8 118.0 . . ?
C10 C9 C3 121.90(9) . . ?
C10 C9 C3 121.90(9) 4 . ?
C10 C9 C10 116.21(19) 4 . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.83(14) . . ?
C11 C10 H10 120.1 . . ?
N3 C11 C10 124.29(15) . . ?
N3 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?

_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_ap7
_audit_block_doi                 10.5517/cc13rnbv
_database_code_depnum_ccdc_archive 'CCDC 1035627'
_audit_update_record             
;
2014-11-22 deposited with the CCDC.
2016-03-02 downloaded from the CCDC.
;
_audit_creation_date             2014-09-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H13 N3 O'
_chemical_formula_sum            'C19 H13 N3 O'
_chemical_formula_weight         299.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N3 O1 C20 H20'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3826(8)
_cell_length_b                   13.1881(11)
_cell_length_c                   11.3683(12)
_cell_angle_alpha                90
_cell_angle_beta                 105.410(10)
_cell_angle_gamma                90
_cell_volume                     1500.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1332
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.1520
_cell_measurement_theta_min      4.7260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7098
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.036
_diffrn_reflns_theta_min         3.464
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -77.00  -32.00   1.0000   25.8750
omega____ theta____ kappa____ phi______ frames
    -       10.2152  179.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
  2 omega  -36.00   63.00   1.0000   25.8750
omega____ theta____ kappa____ phi______ frames
    -      -11.1527   38.0000   60.0000 99

#__ type_ start__ end____ width___ exp.time_
  3 omega  -55.00   13.00   1.0000   25.8750
omega____ theta____ kappa____ phi______ frames
    -      -11.1527  -38.0000 -150.0000 68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0020004000
_diffrn_orient_matrix_UB_12      0.0479760000
_diffrn_orient_matrix_UB_13      0.0276352000
_diffrn_orient_matrix_UB_21      -0.0532997000
_diffrn_orient_matrix_UB_22      0.0149703000
_diffrn_orient_matrix_UB_23      -0.0502178000
_diffrn_orient_matrix_UB_31      -0.0466916000
_diffrn_orient_matrix_UB_32      -0.0191002000
_diffrn_orient_matrix_UB_33      0.0300484000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_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                1542
_reflns_number_total             2653
_reflns_odcompleteness_completeness 99.72
_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 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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    ?
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2653
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.056
_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)+(0.1068P)²+0.0411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1771
_refine_ls_wR_factor_ref         0.2021
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(O1)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=1-FVAR(1)
 Sof(O1A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C17A(H17A), C18A(H18A),
 C19A(H19A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7412(2) 0.00494(17) 0.8504(2) 0.0647(6) Uani 1 1 d . . . . .
N2 N 1.0212(2) -0.16382(18) 0.8701(2) 0.0765(7) Uani 1 1 d . . . . .
N3 N 0.4821(3) 0.1906(2) 0.7384(2) 0.0880(8) Uani 1 1 d . . . . .
C1 C 0.8327(2) -0.04959(18) 0.8125(3) 0.0589(7) Uani 1 1 d . . . . .
C2 C 0.8384(2) -0.04697(18) 0.6952(3) 0.0580(7) Uani 1 1 d . . . . .
H2 H 0.9031 -0.0847 0.6719 0.070 Uiso 1 1 calc R . . . .
C3 C 0.7497(2) 0.01075(19) 0.6097(3) 0.0631(8) Uani 1 1 d . . . . .
C4 C 0.6573(2) 0.06815(19) 0.6502(3) 0.0601(7) Uani 1 1 d . . . . .
H4 H 0.5963 0.1087 0.5954 0.072 Uiso 1 1 calc R . . . .
C5 C 0.6558(2) 0.06516(19) 0.7698(3) 0.0594(7) Uani 1 1 d . . . . .
C6 C 0.9228(2) -0.11462(17) 0.9050(2) 0.0552(7) Uani 1 1 d . . . . .
C7 C 0.9059(3) -0.1244(2) 1.0202(3) 0.0657(7) Uani 1 1 d . . . . .
H7 H 0.8391 -0.0887 1.0429 0.079 Uiso 1 1 calc R . . . .
C8 C 0.9880(3) -0.1865(3) 1.0992(3) 0.0856(9) Uani 1 1 d . . . . .
H8 H 0.9766 -0.1952 1.1770 0.103 Uiso 1 1 calc R . . . .
C9 C 1.0860(3) -0.2360(2) 1.0676(3) 0.0838(9) Uani 1 1 d . . . . .
H9 H 1.1433 -0.2783 1.1231 0.101 Uiso 1 1 calc R . . . .
C10 C 1.1009(3) -0.2236(2) 0.9534(4) 0.0862(10) Uani 1 1 d . . . . .
H10 H 1.1695 -0.2583 0.9322 0.103 Uiso 1 1 calc R . . . .
C11 C 0.5602(2) 0.1264(2) 0.8162(2) 0.0590(7) Uani 1 1 d . . . . .
C12 C 0.5514(3) 0.1164(3) 0.9320(3) 0.0869(10) Uani 1 1 d . . . . .
H12 H 0.6059 0.0709 0.9854 0.104 Uiso 1 1 calc R . . . .
C13 C 0.4652(4) 0.1715(3) 0.9673(4) 0.1057(12) Uani 1 1 d . . . . .
H13 H 0.4572 0.1644 1.0465 0.127 Uiso 1 1 calc R . . . .
C14 C 0.3901(3) 0.2360(3) 0.8951(4) 0.0887(11) Uani 1 1 d . . . . .
H14 H 0.3306 0.2764 0.9225 0.106 Uiso 1 1 calc R . . . .
C15 C 0.3992(4) 0.2436(3) 0.7820(4) 0.1090(13) Uani 1 1 d . . . . .
H15 H 0.3433 0.2893 0.7303 0.131 Uiso 1 1 calc R . . . .
C16 C 0.7518(3) 0.0112(2) 0.4828(3) 0.0661(8) Uani 1 1 d . . . . .
O1 O 0.6637(4) 0.0714(3) 0.4032(5) 0.0746(14) Uani 0.775(11) 1 d . . P A 1
C17 C 0.8325(11) -0.0310(8) 0.4245(12) 0.093(3) Uani 0.775(11) 1 d . . P A 1
H17 H 0.9072 -0.0704 0.4592 0.112 Uiso 0.775(11) 1 calc R . P A 1
C18 C 0.782(2) -0.0040(14) 0.2935(13) 0.122(7) Uani 0.775(11) 1 d . . P A 1
H18 H 0.8142 -0.0277 0.2296 0.146 Uiso 0.775(11) 1 calc R . P A 1
C19 C 0.6899(14) 0.0556(11) 0.2863(8) 0.101(6) Uani 0.775(11) 1 d . . P A 1
H19 H 0.6427 0.0869 0.2144 0.121 Uiso 0.775(11) 1 calc R . P A 1
O1A O 0.8452(18) -0.0567(16) 0.358(2) 0.096(7) Uani 0.225(11) 1 d . . P A 2
C17A C 0.846(3) -0.0645(18) 0.463(3) 0.060(6) Uani 0.225(11) 1 d . . P A 2
H17A H 0.8968 -0.1093 0.5204 0.072 Uiso 0.225(11) 1 calc R . P A 2
C18A C 0.774(3) 0.006(2) 0.267(3) 0.048(6) Uani 0.225(11) 1 d . . P A 2
H18A H 0.7820 0.0145 0.1882 0.058 Uiso 0.225(11) 1 calc R . P A 2
C19A C 0.673(2) 0.062(2) 0.330(4) 0.078(15) Uani 0.225(11) 1 d . . P A 2
H19A H 0.6000 0.1049 0.3003 0.094 Uiso 0.225(11) 1 calc R . P 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
N1 C1 1.350(3) . ?
N1 C5 1.351(3) . ?
N2 C6 1.356(3) . ?
N2 C10 1.337(4) . ?
N3 C11 1.333(3) . ?
N3 C15 1.304(4) . ?
C1 C2 1.350(4) . ?
C1 C6 1.481(4) . ?
C2 C3 1.377(4) . ?
C3 C4 1.392(4) . ?
C3 C16 1.449(4) . ?
C4 C5 1.364(4) . ?
C5 C11 1.481(4) . ?
C6 C7 1.372(4) . ?
C7 C8 1.340(4) . ?
C8 C9 1.337(4) . ?
C9 C10 1.357(4) . ?
C11 C12 1.351(4) . ?
C12 C13 1.296(4) . ?
C13 C14 1.290(5) . ?
C14 C15 1.318(5) . ?
C16 O1 1.359(5) . ?
C16 C17 1.321(12) . ?
C16 C17A 1.46(3) . ?
C16 C19A 1.84(4) . ?
O1 C19 1.440(10) . ?
C17 C18 1.485(19) . ?
C18 C19 1.23(2) . ?
O1A C17A 1.20(5) . ?
O1A C18A 1.38(5) . ?
C18A C19A 1.60(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
C1 N1 C5 119.2(2) . . ?
C10 N2 C6 116.6(3) . . ?
C15 N3 C11 115.8(3) . . ?
N1 C1 C2 121.3(2) . . ?
N1 C1 C6 116.6(3) . . ?
C2 C1 C6 122.1(2) . . ?
C1 C2 C3 121.0(3) . . ?
C2 C3 C4 117.2(3) . . ?
C2 C3 C16 121.4(3) . . ?
C4 C3 C16 121.4(3) . . ?
C5 C4 C3 120.3(3) . . ?
N1 C5 C4 120.9(2) . . ?
N1 C5 C11 117.4(2) . . ?
C4 C5 C11 121.7(2) . . ?
N2 C6 C1 116.9(2) . . ?
N2 C6 C7 122.2(2) . . ?
C7 C6 C1 121.0(2) . . ?
C8 C7 C6 118.5(3) . . ?
C9 C8 C7 120.8(3) . . ?
C8 C9 C10 119.1(3) . . ?
N2 C10 C9 122.8(3) . . ?
N3 C11 C5 117.2(2) . . ?
N3 C11 C12 121.5(3) . . ?
C12 C11 C5 121.3(3) . . ?
C13 C12 C11 118.5(3) . . ?
C14 C13 C12 121.5(4) . . ?
C13 C14 C15 118.9(3) . . ?
N3 C15 C14 123.8(3) . . ?
C3 C16 C17A 109.7(12) . . ?
C3 C16 C19A 145.1(11) . . ?
O1 C16 C3 118.7(3) . . ?
C17 C16 C3 132.6(6) . . ?
C17 C16 O1 108.4(6) . . ?
C17A C16 C19A 104.9(15) . . ?
C16 O1 C19 105.8(6) . . ?
C16 C17 C18 107.5(9) . . ?
C19 C18 C17 106.4(11) . . ?
C18 C19 O1 111.5(11) . . ?
C17A O1A C18A 131(2) . . ?
O1A C17A C16 105.4(15) . . ?
O1A C18A C19A 103(3) . . ?
C18A C19A C16 94.2(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
