# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_g190102b
_database_code_depnum_ccdc_archive 'CCDC 1888665'
loop_
_audit_author_name
_audit_author_address
'Lihua Qiu'
;Soochow University
China
;
_audit_update_record             
;
2019-01-03 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-01-04
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 N2 O'
_chemical_formula_sum            'C14 H12 N2 O'
_chemical_formula_weight         224.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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      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                   7.2536(6)
_cell_length_b                   9.2341(9)
_cell_length_c                   9.3515(10)
_cell_angle_alpha                85.065(8)
_cell_angle_beta                 81.059(8)
_cell_angle_gamma                68.355(8)
_cell_volume                     574.85(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2866
_cell_measurement_temperature    295.25(10)
_cell_measurement_theta_max      26.7120
_cell_measurement_theta_min      4.4580
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11188
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.351
_diffrn_reflns_theta_min         3.049
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1019201000
_diffrn_orient_matrix_UB_12      0.0211476000
_diffrn_orient_matrix_UB_13      -0.0093868000
_diffrn_orient_matrix_UB_21      0.0242147000
_diffrn_orient_matrix_UB_22      0.0139071000
_diffrn_orient_matrix_UB_23      -0.0750807000
_diffrn_orient_matrix_UB_31      0.0171709000
_diffrn_orient_matrix_UB_32      -0.0787107000
_diffrn_orient_matrix_UB_33      -0.0132653000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1816
_reflns_number_total             3111
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) (compiled Aug 2 2013,16:46:58)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.016
_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)+(0.0757P)²+0.0485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1669
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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
O1 O 0.17502(15) 1.23770(11) 0.48013(12) 0.0715(3) Uani 1 1 d . . . . .
N1 N 0.32413(19) 1.17202(14) 0.25299(15) 0.0698(4) Uani 1 1 d . . . . .
N2 N 0.39323(19) 0.77138(14) 0.39918(13) 0.0670(4) Uani 1 1 d . . . . .
C1 C 0.2378(2) 1.07869(16) 0.47365(18) 0.0614(4) Uani 1 1 d . . . . .
C2 C 0.2162(2) 0.97081(17) 0.58287(16) 0.0612(4) Uani 1 1 d . . . . .
C3 C 0.1218(3) 1.0027(2) 0.72564(19) 0.0759(5) Uani 1 1 d . . . . .
H3 H 0.0668 1.1049 0.7562 0.091 Uiso 1 1 calc R . . . .
C4 C 0.1111(3) 0.8840(2) 0.81918(19) 0.0853(5) Uani 1 1 d . . . . .
H4 H 0.0475 0.9061 0.9134 0.102 Uiso 1 1 calc R . . . .
C5 C 0.1932(3) 0.7307(2) 0.77640(18) 0.0784(5) Uani 1 1 d . . . . .
H5 H 0.1850 0.6511 0.8421 0.094 Uiso 1 1 calc R . . . .
C6 C 0.2859(2) 0.69582(18) 0.63896(17) 0.0681(4) Uani 1 1 d . . . . .
H6 H 0.3407 0.5924 0.6117 0.082 Uiso 1 1 calc R . . . .
C7 C 0.2998(2) 0.81443(17) 0.53741(16) 0.0599(4) Uani 1 1 d . . . . .
C8 C 0.4077(2) 0.87938(17) 0.30043(17) 0.0668(4) Uani 1 1 d . . . . .
C9 C 0.3287(2) 1.03839(16) 0.33697(17) 0.0626(4) Uani 1 1 d . . . . .
C10 C 0.2336(2) 1.28306(18) 0.3418(2) 0.0720(4) Uani 1 1 d . . . . .
C11 C 0.1833(3) 1.45276(18) 0.3139(2) 0.0924(6) Uani 1 1 d . . . . .
H11A H 0.0425 1.5063 0.3417 0.139 Uiso 1 1 calc GR . . . .
H11B H 0.2173 1.4726 0.2127 0.139 Uiso 1 1 calc GR . . . .
H11C H 0.2574 1.4893 0.3693 0.139 Uiso 1 1 calc GR . . . .
C12 C 0.5051(3) 0.83443(19) 0.15254(18) 0.0826(5) Uani 1 1 d . . . . .
H12 H 0.4955 0.9214 0.0825 0.099 Uiso 1 1 calc R . . . .
C13 C 0.6913(3) 0.6967(2) 0.1289(2) 0.0935(6) Uani 1 1 d . . . . .
H13A H 0.7924 0.7028 0.0500 0.112 Uiso 1 1 calc R . . . .
H13B H 0.7434 0.6365 0.2136 0.112 Uiso 1 1 calc R . . . .
C14 C 0.5088(3) 0.6903(2) 0.0920(2) 0.0968(6) Uani 1 1 d . . . . .
H14A H 0.4467 0.6264 0.1536 0.116 Uiso 1 1 calc R . . . .
H14B H 0.4957 0.6927 -0.0100 0.116 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
O1 C1 1.3713(16) . ?
O1 C10 1.377(2) . ?
N1 C9 1.3970(19) . ?
N1 C10 1.286(2) . ?
N2 C7 1.380(2) . ?
N2 C8 1.3217(19) . ?
C1 C2 1.397(2) . ?
C1 C9 1.358(2) . ?
C2 C3 1.404(2) . ?
C2 C7 1.419(2) . ?
C3 C4 1.360(2) . ?
C4 C5 1.386(2) . ?
C5 C6 1.360(2) . ?
C6 C7 1.409(2) . ?
C8 C9 1.416(2) . ?
C8 C12 1.471(2) . ?
C10 C11 1.481(2) . ?
C12 C13 1.476(2) . ?
C12 C14 1.480(2) . ?
C13 C14 1.441(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
C1 O1 C10 103.39(12) . . ?
C10 N1 C9 103.45(14) . . ?
C8 N2 C7 119.73(13) . . ?
O1 C1 C2 128.67(14) . . ?
C9 C1 O1 107.86(13) . . ?
C9 C1 C2 123.46(13) . . ?
C1 C2 C3 127.06(14) . . ?
C1 C2 C7 113.37(14) . . ?
C3 C2 C7 119.57(14) . . ?
C4 C3 C2 119.95(16) . . ?
C3 C4 C5 121.05(16) . . ?
C6 C5 C4 120.46(16) . . ?
C5 C6 C7 120.79(15) . . ?
N2 C7 C2 123.93(14) . . ?
N2 C7 C6 117.90(13) . . ?
C6 C7 C2 118.17(14) . . ?
N2 C8 C9 119.97(15) . . ?
N2 C8 C12 119.99(14) . . ?
C9 C8 C12 120.05(14) . . ?
N1 C9 C8 130.65(15) . . ?
C1 C9 N1 109.80(13) . . ?
C1 C9 C8 119.55(14) . . ?
O1 C10 C11 116.20(15) . . ?
N1 C10 O1 115.50(14) . . ?
N1 C10 C11 128.30(17) . . ?
C8 C12 C13 120.27(15) . . ?
C8 C12 C14 120.80(15) . . ?
C13 C12 C14 58.35(12) . . ?
C14 C13 C12 60.95(13) . . ?
C13 C14 C12 60.70(13) . . ?


_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_G190327A
_database_code_depnum_ccdc_archive 'CCDC 1906218'
loop_
_audit_author_name
_audit_author_address
'Lihua Qiu'
;Soochow University
China
;
_audit_update_record             
;
2019-03-28 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-03-28
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_chemical_formula_moiety         'C25 H15 N3 O'
_chemical_formula_sum            'C25 H15 N3 O'
_chemical_formula_weight         373.42
_chemical_oxdiff_formula         CHON
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

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

_symmetry_Int_Tables_number      14
_cell_length_a                   9.8811(7)
_cell_length_b                   14.4238(7)
_cell_length_c                   13.7948(9)
_cell_angle_alpha                90
_cell_angle_beta                 109.258(7)
_cell_angle_gamma                90
_cell_volume                     1856.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3791
_cell_measurement_temperature    279(7)
_cell_measurement_theta_max      26.5510
_cell_measurement_theta_min      3.5730
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60676
_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.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light pink'
_exptl_crystal_density_diffrn    1.3362
_exptl_crystal_description       block
_exptl_crystal_F_000             776.3214
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16777
_diffrn_reflns_theta_full        26.3722
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.82
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      279(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9989
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -66.00   43.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       10.4965  -77.0000   90.0000 109

#__ type_ start__ end____ width___ exp.time_
  2 omega  -14.00   71.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       10.4965   38.0000  -90.0000 85

#__ type_ start__ end____ width___ exp.time_
  3 omega  -22.00   10.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.2778  -99.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -50.00   55.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.2778   19.0000   60.0000 105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0390118000
_diffrn_orient_matrix_UB_12      -0.0414302000
_diffrn_orient_matrix_UB_13      -0.0175784000
_diffrn_orient_matrix_UB_21      -0.0642713000
_diffrn_orient_matrix_UB_22      0.0260235000
_diffrn_orient_matrix_UB_23      -0.0191814000
_diffrn_orient_matrix_UB_31      0.0115747000
_diffrn_orient_matrix_UB_32      0.0047825000
_diffrn_orient_matrix_UB_33      -0.0478371000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -12
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -7
_reflns_number_gt                2608
_reflns_number_total             3785
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.1967
_refine_diff_density_min         -0.2405
_refine_diff_density_rms         0.0522
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             7.2119
_refine_ls_goodness_of_fit_ref   1.0655
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3785
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.0655
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²+0.2642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1255
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C12(H12), C11(H11), C5(H5), C4(H4), C3(H3), C2(H2),
 C1(H1), C25(H25), C24(H24), C23(H23), C22(H22), C21(H21), C19(H19)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
O1 O 0.40279(12) 0.18181(7) 0.37543(8) 0.0456(3) Uani 1.000000 .
N1 N 0.49646(15) 0.13290(9) 0.25574(10) 0.0450(4) Uani 1.000000 .
N2 N 0.6506(2) 0.31893(12) 0.17267(14) 0.0762(5) Uani 1.000000 .
N3 N 0.38089(15) -0.09720(9) 0.32160(10) 0.0453(3) Uani 1.000000 .
C1 C 0.4293(2) -0.16148(13) 0.14266(14) 0.0588(5) Uani 1.000000 .
C2 C 0.4678(2) -0.19658(15) 0.06277(16) 0.0709(6) Uani 1.000000 .
C3 C 0.5645(2) -0.15093(15) 0.02853(15) 0.0686(6) Uani 1.000000 .
C4 C 0.6249(2) -0.07011(14) 0.07471(15) 0.0650(6) Uani 1.000000 .
C5 C 0.5862(2) -0.03329(13) 0.15485(13) 0.0544(5) Uani 1.000000 .
C6 C 0.48704(18) -0.07824(11) 0.18928(12) 0.0449(4) Uani 1.000000 .
C7 C 0.43915(17) -0.03958(11) 0.27211(12) 0.0414(4) Uani 1.000000 .
C8 C 0.44552(17) 0.05662(11) 0.29610(12) 0.0405(4) Uani 1.000000 .
C9 C 0.38928(17) 0.08722(11) 0.36865(11) 0.0405(4) Uani 1.000000 .
C10 C 0.32621(17) 0.02950(11) 0.42325(11) 0.0414(4) Uani 1.000000 .
C11 C 0.26598(19) 0.05661(12) 0.49807(12) 0.0498(4) Uani 1.000000 .
C12 C 0.2068(2) -0.00833(13) 0.54309(14) 0.0576(5) Uani 1.000000 .
C13 C 0.2067(2) -0.10199(14) 0.51646(14) 0.0589(5) Uani 1.000000 .
C14 C 0.26500(19) -0.12958(12) 0.44473(13) 0.0519(4) Uani 1.000000 .
C15 C 0.32650(17) -0.06496(11) 0.39524(12) 0.0423(4) Uani 1.000000 .
C16 C 0.46854(18) 0.20265(11) 0.30444(12) 0.0434(4) Uani 1.000000 .
C17 C 0.49921(19) 0.29996(11) 0.29173(12) 0.0450(4) Uani 1.000000 .
C18 C 0.5836(2) 0.31245(12) 0.22548(14) 0.0531(5) Uani 1.000000 .
C19 C 0.44804(19) 0.36860(11) 0.33546(12) 0.0472(4) Uani 1.000000 .
C20 C 0.46023(19) 0.46891(12) 0.33169(12) 0.0486(4) Uani 1.000000 .
C21 C 0.5376(3) 0.51618(14) 0.28022(17) 0.0736(6) Uani 1.000000 .
C22 C 0.5469(3) 0.61157(15) 0.2845(2) 0.0937(8) Uani 1.000000 .
C23 C 0.4773(3) 0.66114(15) 0.33902(19) 0.0864(8) Uani 1.000000 .
C24 C 0.3984(3) 0.61600(15) 0.38836(17) 0.0737(6) Uani 1.000000 .
C25 C 0.3900(2) 0.52109(13) 0.38507(14) 0.0594(5) Uani 1.000000 .
H14 H 0.26424(19) -0.19211(12) 0.42811(13) 0.0623(5) Uiso 1.000000 R
H13 H 0.1663(2) -0.14577(14) 0.54819(14) 0.0707(6) Uiso 1.000000 R
H12 H 0.1660(2) 0.00959(13) 0.59204(14) 0.0692(6) Uiso 1.000000 R
H11 H 0.26667(19) 0.11865(12) 0.51661(12) 0.0598(5) Uiso 1.000000 R
H5 H 0.6272(2) 0.02193(13) 0.18555(13) 0.0653(6) Uiso 1.000000 R
H4 H 0.6922(2) -0.03967(14) 0.05237(15) 0.0780(7) Uiso 1.000000 R
H3 H 0.5892(2) -0.17475(15) -0.02604(15) 0.0823(7) Uiso 1.000000 R
H2 H 0.4277(2) -0.25189(15) 0.03177(16) 0.0851(7) Uiso 1.000000 R
H1 H 0.3642(2) -0.19361(13) 0.16572(14) 0.0706(6) Uiso 1.000000 R
H25 H 0.3360(2) 0.49096(13) 0.41942(14) 0.0713(6) Uiso 1.000000 R
H24 H 0.3501(3) 0.64947(15) 0.42440(17) 0.0885(8) Uiso 1.000000 R
H23 H 0.4842(3) 0.72545(15) 0.34209(19) 0.1037(9) Uiso 1.000000 R
H22 H 0.6005(3) 0.64250(15) 0.2503(2) 0.1124(10) Uiso 1.000000 R
H21 H 0.5839(3) 0.48329(14) 0.24235(17) 0.0884(8) Uiso 1.000000 R
H19 H 0.39480(19) 0.34818(11) 0.37573(12) 0.0567(5) Uiso 1.000000 R


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
O1 C9 1.3710(19) . ?
O1 C16 1.3751(19) . ?
N1 C8 1.400(2) . ?
N1 C16 1.289(2) . ?
N2 C18 1.139(2) . ?
N3 C7 1.322(2) . ?
N3 C15 1.377(2) . ?
C1 C2 1.375(3) . ?
C1 C6 1.392(2) . ?
C2 C3 1.366(3) . ?
C3 C4 1.368(3) . ?
C4 C5 1.389(2) . ?
C5 C6 1.383(2) . ?
C6 C7 1.482(2) . ?
C7 C8 1.423(2) . ?
C8 C9 1.368(2) . ?
C9 C10 1.399(2) . ?
C10 C11 1.406(2) . ?
C10 C15 1.417(2) . ?
C11 C12 1.358(2) . ?
C12 C13 1.400(3) . ?
C13 C14 1.359(2) . ?
C14 C15 1.406(2) . ?
C16 C17 1.459(2) . ?
C17 C18 1.437(3) . ?
C17 C19 1.342(2) . ?
C19 C20 1.454(2) . ?
C20 C21 1.383(3) . ?
C20 C25 1.388(2) . ?
C21 C22 1.379(3) . ?
C22 C23 1.376(3) . ?
C23 C24 1.358(3) . ?
C24 C25 1.371(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
C16 O1 C9 103.13(12) . . ?
C16 N1 C8 103.84(13) . . ?
C15 N3 C7 120.73(14) . . ?
C6 C1 C2 120.54(19) . . ?
C3 C2 C1 120.61(19) . . ?
C4 C3 C2 119.81(18) . . ?
C5 C4 C3 120.29(19) . . ?
C6 C5 C4 120.42(18) . . ?
C5 C6 C1 118.31(16) . . ?
C7 C6 C1 119.61(16) . . ?
C7 C6 C5 122.06(15) . . ?
C6 C7 N3 117.76(14) . . ?
C8 C7 N3 119.09(14) . . ?
C8 C7 C6 123.04(14) . . ?
C7 C8 N1 131.92(14) . . ?
C9 C8 N1 108.88(13) . . ?
C9 C8 C7 119.15(14) . . ?
C8 C9 O1 108.48(13) . . ?
C10 C9 O1 127.30(14) . . ?
C10 C9 C8 124.21(14) . . ?
C11 C10 C9 126.94(15) . . ?
C15 C10 C9 112.59(14) . . ?
C15 C10 C11 120.47(15) . . ?
C12 C11 C10 119.61(16) . . ?
C13 C12 C11 120.58(17) . . ?
C14 C13 C12 120.66(17) . . ?
C15 C14 C13 120.96(16) . . ?
C10 C15 N3 124.22(14) . . ?
C14 C15 N3 118.06(15) . . ?
C14 C15 C10 117.71(15) . . ?
N1 C16 O1 115.66(14) . . ?
C17 C16 O1 117.49(14) . . ?
C17 C16 N1 126.84(15) . . ?
C18 C17 C16 112.59(14) . . ?
C19 C17 C16 122.13(16) . . ?
C19 C17 C18 125.24(15) . . ?
C17 C18 N2 177.51(19) . . ?
C20 C19 C17 132.07(16) . . ?
C21 C20 C19 125.11(17) . . ?
C25 C20 C19 117.31(17) . . ?
C25 C20 C21 117.57(17) . . ?
C22 C21 C20 120.7(2) . . ?
C23 C22 C21 120.2(2) . . ?
C24 C23 C22 119.9(2) . . ?
C25 C24 C23 120.0(2) . . ?
C24 C25 C20 121.6(2) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
