# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_161208_cm_1
_database_code_depnum_ccdc_archive 'CCDC 1822148'
_audit_update_record             
;
2018-02-05 deposited with the CCDC.
2018-08-21 downloaded from the CCDC.
;
_audit_creation_date             2016-12-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H6 N4, 0.5(H4 O2)'
_chemical_formula_sum            'C10 H8 N4 O'
_chemical_formula_weight         200.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   3.7576(5)
_cell_length_b                   14.4280(16)
_cell_length_c                   9.4611(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.599(12)
_cell_angle_gamma                90.00
_cell_volume                     504.18(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    672
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4334
_cell_measurement_theta_min      3.5672
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.29
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3103
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.57
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0559174000
_diffrn_orient_matrix_UB_12      -0.0468024000
_diffrn_orient_matrix_UB_13      -0.0028016000
_diffrn_orient_matrix_UB_21      0.0327074000
_diffrn_orient_matrix_UB_22      -0.0021176000
_diffrn_orient_matrix_UB_23      0.0762068000
_diffrn_orient_matrix_UB_31      -0.1808074000
_diffrn_orient_matrix_UB_32      -0.0148692000
_diffrn_orient_matrix_UB_33      -0.0020416000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                618
_reflns_number_total             924
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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         0.490
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         924
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0715
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1409P)²+0.1816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2194
_refine_ls_wR_factor_ref         0.2520
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: O1(0.5) H1A(0.5) H1B(0.5)
3.a Free rotating group:
 O1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.0989(7) 0.37739(19) 0.3091(3) 0.0523(9) Uani 1 d . . .
N2 N 0.5580(7) 0.68190(19) 0.4147(3) 0.0557(9) Uani 1 d . . .
C1 C 0.0808(9) 0.2920(2) 0.3542(4) 0.0570(10) Uani 1 d . . .
H1 H -0.0513 0.2489 0.2928 0.068 Uiso 1 calc . . R
C2 C 0.2994(7) 0.4383(2) 0.4039(3) 0.0423(9) Uani 1 d . . .
C3 C 0.3329(7) 0.5290(2) 0.3630(3) 0.0470(9) Uani 1 d . . .
H3 H 0.2225 0.5484 0.2717 0.056 Uiso 1 calc . . R
C4 C 0.5320(7) 0.5917(2) 0.4582(3) 0.0421(9) Uani 1 d . . .
C5 C 0.7475(9) 0.7371(3) 0.5086(4) 0.0585(10) Uani 1 d . . .
H5 H 0.7701 0.7988 0.4835 0.070 Uiso 1 calc . . R
O1 O -0.2347(18) 0.4422(4) 0.0261(5) 0.0821(19) Uani 0.50 d . . .
H1A H -0.2099 0.4251 0.1133 0.123 Uiso 0.50 d . . G
H1B H -0.0625 0.4785 0.0164 0.123 Uiso 0.50 d . . G


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.309(4) . ?
N1 C2 1.377(4) . ?
N2 C4 1.374(4) . ?
N2 C5 1.303(4) . ?
C1 H1 0.9300 . ?
C1 C5 1.403(5) 3_666 ?
C2 C3 1.377(4) . ?
C2 C4 1.409(4) 3_666 ?
C3 H3 0.9300 . ?
C3 C4 1.393(4) . ?
C4 C2 1.409(4) 3_666 ?
C5 C1 1.403(5) 3_666 ?
C5 H5 0.9300 . ?
O1 H1A 0.8504 . ?
O1 H1B 0.8499 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 116.3(3) . . ?
C5 N2 C4 115.7(3) . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C5 122.7(3) . 3_666 ?
C5 C1 H1 118.6 3_666 . ?
N1 C2 C4 120.4(3) . 3_666 ?
C3 C2 N1 119.4(3) . . ?
C3 C2 C4 120.2(3) . 3_666 ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
N2 C4 C2 121.6(3) . 3_666 ?
N2 C4 C3 118.7(3) . . ?
C3 C4 C2 119.7(3) . 3_666 ?
N2 C5 C1 123.3(3) . 3_666 ?
N2 C5 H5 118.4 . . ?
C1 C5 H5 118.4 3_666 . ?
H1A O1 H1B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 179.4(2) . . . . ?
C1 N1 C2 C3 179.4(3) . . . . ?
C1 N1 C2 C4 -0.8(4) . . . 3_666 ?
C2 N1 C1 C5 0.3(5) . . . 3_666 ?
C2 C3 C4 N2 -179.5(3) . . . . ?
C2 C3 C4 C2 0.4(5) . . . 3_666 ?
C4 N2 C5 C1 0.5(5) . . . 3_666 ?
C4 C2 C3 C4 -0.4(5) 3_666 . . . ?
C5 N2 C4 C2 0.1(4) . . . 3_666 ?
C5 N2 C4 C3 179.9(3) . . . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cming6cult
_database_code_depnum_ccdc_archive 'CCDC 1822244'
_audit_update_record             
;
2018-02-06 deposited with the CCDC.
2018-08-21 downloaded from the CCDC.
;
_audit_creation_date             2016-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C34 H22 N4'
_chemical_formula_sum            'C34 H22 N4'
_chemical_formula_weight         486.55
_chemical_melting_point          ?
_chemical_oxdiff_formula         'ph6 N4'
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      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                   5.7720(4)
_cell_length_b                   9.9613(6)
_cell_length_c                   10.8529(8)
_cell_angle_alpha                87.644(5)
_cell_angle_beta                 77.477(6)
_cell_angle_gamma                89.901(5)
_cell_volume                     608.63(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1643
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.2170
_cell_measurement_theta_min      5.9680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             254
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3152
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.990
_diffrn_reflns_theta_min         4.176
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   37.00  122.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -125.0000  120.0000 85

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   31.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.4453   37.0000   90.0000 80

#__ type_ start__ end____ width___ exp.time_
  3 omega  -71.00   27.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.4453   77.0000  -60.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega  -69.00   34.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.4453   57.0000 -180.0000 103

#__ type_ start__ end____ width___ exp.time_
  5 omega   35.00   87.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
  6 omega   35.00   88.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega   81.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000  -60.0000 97

#__ type_ start__ end____ width___ exp.time_
  8 omega   80.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000 -150.0000 98

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00   79.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000 -180.0000 40

#__ type_ start__ end____ width___ exp.time_
 10 omega   36.00   76.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00  122.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -77.0000  -90.0000 83

#__ type_ start__ end____ width___ exp.time_
 12 omega   33.00   84.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  -60.0000 51

#__ type_ start__ end____ width___ exp.time_
 13 omega   33.00  102.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000 -150.0000 69
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1606893000
_diffrn_orient_matrix_UB_12      -0.0541618000
_diffrn_orient_matrix_UB_13      0.0867668000
_diffrn_orient_matrix_UB_21      0.1447591000
_diffrn_orient_matrix_UB_22      -0.0785589000
_diffrn_orient_matrix_UB_23      -0.1098060000
_diffrn_orient_matrix_UB_31      0.1672722000
_diffrn_orient_matrix_UB_32      0.1218799000
_diffrn_orient_matrix_UB_33      -0.0399321000
_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_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1874
_reflns_number_total             2102
_reflns_odcompleteness_completeness 98.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.002
_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)+(0.0830P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1112
_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:
 C7(H7), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26)
;
_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 0.55459(16) 0.47040(9) 0.15922(9) 0.0193(2) Uani 1 1 d . . . . .
C2 C 0.48400(19) 0.34886(11) 0.20334(10) 0.0188(3) Uani 1 1 d . . . . .
C3 C 0.62724(19) 0.23159(11) 0.16057(10) 0.0188(3) Uani 1 1 d . . . . .
N4 N 0.83982(16) 0.24409(9) 0.08815(8) 0.0191(2) Uani 1 1 d . . . . .
C5 C 0.92091(19) 0.37129(11) 0.04586(10) 0.0188(3) Uani 1 1 d . . . . .
C6 C 0.77142(19) 0.48477(11) 0.07762(10) 0.0185(3) Uani 1 1 d . . . . .
C7 C 0.85348(19) 0.61278(10) 0.03090(10) 0.0189(3) Uani 1 1 d . . . . .
H7 H 0.7553 0.6888 0.0515 0.023 Uiso 1 1 calc R . . . .
C11 C 0.25620(19) 0.33947(11) 0.29839(10) 0.0200(3) Uani 1 1 d . . . . .
C12 C 0.08592(19) 0.43920(11) 0.29555(11) 0.0207(3) Uani 1 1 d . . . . .
H12 H 0.1190 0.5111 0.2339 0.025 Uiso 1 1 calc R . . . .
C13 C -0.1297(2) 0.43447(11) 0.38131(11) 0.0234(3) Uani 1 1 d . . . . .
H13 H -0.2438 0.5025 0.3777 0.028 Uiso 1 1 calc R . . . .
C14 C -0.1801(2) 0.33059(12) 0.47271(11) 0.0271(3) Uani 1 1 d . . . . .
H14 H -0.3298 0.3261 0.5302 0.032 Uiso 1 1 calc R . . . .
C15 C -0.0103(2) 0.23359(12) 0.47932(11) 0.0273(3) Uani 1 1 d . . . . .
H15 H -0.0426 0.1638 0.5431 0.033 Uiso 1 1 calc R . . . .
C16 C 0.2062(2) 0.23754(11) 0.39383(11) 0.0234(3) Uani 1 1 d . . . . .
H16 H 0.3216 0.1709 0.3998 0.028 Uiso 1 1 calc R . . . .
C21 C 0.54207(19) 0.09036(11) 0.18936(10) 0.0200(3) Uani 1 1 d . . . . .
C22 C 0.3407(2) 0.04578(11) 0.15108(11) 0.0230(3) Uani 1 1 d . . . . .
H22 H 0.2467 0.1078 0.1148 0.028 Uiso 1 1 calc R . . . .
C23 C 0.2776(2) -0.08961(12) 0.16600(11) 0.0246(3) Uani 1 1 d . . . . .
H23 H 0.1428 -0.1203 0.1379 0.029 Uiso 1 1 calc R . . . .
C24 C 0.4114(2) -0.18015(11) 0.22190(11) 0.0260(3) Uani 1 1 d . . . . .
H24 H 0.3678 -0.2725 0.2323 0.031 Uiso 1 1 calc R . . . .
C25 C 0.6087(2) -0.13536(11) 0.26251(12) 0.0270(3) Uani 1 1 d . . . . .
H25 H 0.6983 -0.1969 0.3021 0.032 Uiso 1 1 calc R . . . .
C26 C 0.6756(2) -0.00059(11) 0.24536(11) 0.0237(3) Uani 1 1 d . . . . .
H26 H 0.8125 0.0294 0.2719 0.028 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 1.3155(14) . ?
N1 C6 1.3714(15) . ?
C2 C3 1.4623(15) . ?
C2 C11 1.4852(15) . ?
C3 N4 1.3088(14) . ?
C3 C21 1.4893(14) . ?
N4 C5 1.3771(14) . ?
C5 C6 1.4286(16) . ?
C5 C7 1.3908(16) 2_765 ?
C6 C7 1.3972(15) . ?
C7 C5 1.3908(16) 2_765 ?
C11 C12 1.4003(16) . ?
C11 C16 1.4043(16) . ?
C12 C13 1.3825(16) . ?
C13 C14 1.3896(17) . ?
C14 C15 1.3861(18) . ?
C15 C16 1.3849(17) . ?
C21 C22 1.3955(16) . ?
C21 C26 1.3928(16) . ?
C22 C23 1.3913(16) . ?
C23 C24 1.3904(18) . ?
C24 C25 1.3876(18) . ?
C25 C26 1.3915(16) . ?

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 C6 118.28(10) . . ?
N1 C2 C3 120.67(10) . . ?
N1 C2 C11 116.27(10) . . ?
C3 C2 C11 123.06(10) . . ?
C2 C3 C21 123.69(10) . . ?
N4 C3 C2 121.59(10) . . ?
N4 C3 C21 114.65(9) . . ?
C3 N4 C5 118.15(9) . . ?
N4 C5 C6 120.11(10) . . ?
N4 C5 C7 119.24(10) . 2_765 ?
C7 C5 C6 120.63(10) 2_765 . ?
N1 C6 C5 120.73(10) . . ?
N1 C6 C7 119.70(10) . . ?
C7 C6 C5 119.46(10) . . ?
C5 C7 C6 119.91(10) 2_765 . ?
C12 C11 C2 118.64(10) . . ?
C12 C11 C16 118.25(10) . . ?
C16 C11 C2 123.07(10) . . ?
C13 C12 C11 120.88(10) . . ?
C12 C13 C14 120.28(11) . . ?
C15 C14 C13 119.49(11) . . ?
C16 C15 C14 120.61(11) . . ?
C15 C16 C11 120.42(11) . . ?
C22 C21 C3 120.46(10) . . ?
C26 C21 C3 119.62(10) . . ?
C26 C21 C22 119.70(10) . . ?
C23 C22 C21 119.97(11) . . ?
C24 C23 C22 120.16(11) . . ?
C25 C24 C23 119.88(10) . . ?
C24 C25 C26 120.22(11) . . ?
C25 C26 C21 120.03(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N4 7.32(16) . . . . ?
N1 C2 C3 C21 -169.57(10) . . . . ?
N1 C2 C11 C12 27.62(14) . . . . ?
N1 C2 C11 C16 -150.23(11) . . . . ?
N1 C6 C7 C5 176.18(9) . . . 2_765 ?
C2 N1 C6 C5 -2.71(15) . . . . ?
C2 N1 C6 C7 -178.82(9) . . . . ?
C2 C3 N4 C5 -4.15(15) . . . . ?
C2 C3 C21 C22 59.15(15) . . . . ?
C2 C3 C21 C26 -126.28(12) . . . . ?
C2 C11 C12 C13 179.48(10) . . . . ?
C2 C11 C16 C15 -179.57(10) . . . . ?
C3 C2 C11 C12 -153.16(11) . . . . ?
C3 C2 C11 C16 28.99(16) . . . . ?
C3 N4 C5 C6 -2.09(15) . . . . ?
C3 N4 C5 C7 179.81(9) . . . 2_765 ?
C3 C21 C22 C23 172.93(10) . . . . ?
C3 C21 C26 C25 -174.36(10) . . . . ?
N4 C3 C21 C22 -117.94(11) . . . . ?
N4 C3 C21 C26 56.64(14) . . . . ?
N4 C5 C6 N1 5.78(16) . . . . ?
N4 C5 C6 C7 -178.09(9) . . . . ?
C5 C6 C7 C5 0.01(17) . . . 2_765 ?
C6 N1 C2 C3 -3.49(15) . . . . ?
C6 N1 C2 C11 175.75(9) . . . . ?
C7 C5 C6 N1 -176.14(9) 2_765 . . . ?
C7 C5 C6 C7 -0.01(18) 2_765 . . . ?
C11 C2 C3 N4 -171.87(9) . . . . ?
C11 C2 C3 C21 11.24(16) . . . . ?
C11 C12 C13 C14 0.49(16) . . . . ?
C12 C11 C16 C15 2.57(16) . . . . ?
C12 C13 C14 C15 1.64(17) . . . . ?
C13 C14 C15 C16 -1.63(18) . . . . ?
C14 C15 C16 C11 -0.51(17) . . . . ?
C16 C11 C12 C13 -2.57(16) . . . . ?
C21 C3 N4 C5 173.00(9) . . . . ?
C21 C22 C23 C24 1.62(17) . . . . ?
C22 C21 C26 C25 0.25(17) . . . . ?
C22 C23 C24 C25 -0.20(17) . . . . ?
C23 C24 C25 C26 -1.19(18) . . . . ?
C24 C25 C26 C21 1.16(18) . . . . ?
C26 C21 C22 C23 -1.64(17) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-08-22
_olex2_submission_special_instructions 'No special instructions were received'
