# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1938714'
loop_
_audit_author_name
_audit_author_address
'Vitalii Suslonov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-12-16 downloaded from the CCDC.
;
_audit_creation_date             2019-07-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 F3 N2 O2'
_chemical_formula_sum            'C15 H17 F3 N2 O2'
_chemical_formula_weight         314.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         ' O4 C30 N4 F6'
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'
F F 0.0171 0.0103 '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                   5.1066(12)
_cell_length_b                   11.5568(13)
_cell_length_c                   12.7664(13)
_cell_angle_alpha                100.531(9)
_cell_angle_beta                 94.646(14)
_cell_angle_gamma                100.547(15)
_cell_volume                     723.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1953
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.1860
_cell_measurement_theta_min      3.2840
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72995
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6124
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         3.269
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -69.00  -42.00   1.0000   14.3600
omega____ theta____ kappa____ phi______ frames
    -      -25.5873 -178.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   20.00   61.00   1.0000   14.3600
omega____ theta____ kappa____ phi______ frames
    -       26.6811  -99.0000  -30.0000 41

#__ type_ start__ end____ width___ exp.time_
  3 omega   52.00   97.00   1.0000   14.3600
omega____ theta____ kappa____ phi______ frames
    -       26.6811 -178.0000 -120.0000 45

#__ type_ start__ end____ width___ exp.time_
  4 omega  -21.00   69.00   1.0000   14.3600
omega____ theta____ kappa____ phi______ frames
    -       26.6811  -99.0000   60.0000 90

#__ type_ start__ end____ width___ exp.time_
  5 omega   40.00   69.00   1.0000   14.3600
omega____ theta____ kappa____ phi______ frames
    -       26.6811  -99.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  -38.00   39.00   1.0000   14.3600
omega____ theta____ kappa____ phi______ frames
    -       26.6811  -57.0000 -180.0000 77

#__ type_ start__ end____ width___ exp.time_
  7 omega  -17.00  100.00   1.0000   14.3600
omega____ theta____ kappa____ phi______ frames
    -       26.6811   19.0000    0.0000 117

#__ type_ start__ end____ width___ exp.time_
  8 omega  -47.00  -22.00   1.0000   14.3600
omega____ theta____ kappa____ phi______ frames
    -      -25.5873  -38.0000   60.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1223654000
_diffrn_orient_matrix_UB_12      -0.0417240000
_diffrn_orient_matrix_UB_13      -0.0031574000
_diffrn_orient_matrix_UB_21      0.0725814000
_diffrn_orient_matrix_UB_22      -0.0445789000
_diffrn_orient_matrix_UB_23      0.0095302000
_diffrn_orient_matrix_UB_31      -0.0021268000
_diffrn_orient_matrix_UB_32      0.0182900000
_diffrn_orient_matrix_UB_33      0.0560195000
_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                2644
_reflns_number_total             3326
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.064
_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)+(0.0631P)²+0.0776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1328
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B), C7(H7A,H7B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C10(H10), C14(H14), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F3 F 0.0207(2) 0.00823(9) 0.73388(8) 0.0307(3) Uani 1 1 d . . . . .
F2 F -0.1947(2) 0.14658(9) 0.78669(8) 0.0315(3) Uani 1 1 d . . . . .
F1 F -0.3527(2) 0.01172(10) 0.64502(8) 0.0348(3) Uani 1 1 d . . . . .
O1 O 1.2150(2) 0.57617(10) 0.60296(8) 0.0227(3) Uani 1 1 d . . . . .
O2 O 0.6916(2) 0.41162(10) 0.78294(8) 0.0237(3) Uani 1 1 d . . . . .
N1 N 0.8315(3) 0.45383(12) 0.62655(10) 0.0185(3) Uani 1 1 d . . . . .
H1 H 0.7896 0.4372 0.5565 0.022 Uiso 1 1 calc R . . . .
N2 N 1.1290(3) 0.56977(12) 0.77268(10) 0.0198(3) Uani 1 1 d . . . . .
H2 H 1.0126 0.5411 0.8134 0.024 Uiso 1 1 calc R . . . .
C3 C 1.3787(3) 0.65156(14) 0.82424(11) 0.0182(3) Uani 1 1 d . . . . .
H3 H 1.5252 0.6357 0.7795 0.022 Uiso 1 1 calc R . . . .
C1 C 1.0716(3) 0.53722(13) 0.66685(12) 0.0175(3) Uani 1 1 d . . . . .
C9 C 0.4119(3) 0.31038(14) 0.62389(12) 0.0184(3) Uani 1 1 d . . . . .
C4 C 1.4468(3) 0.62301(14) 0.93355(11) 0.0204(3) Uani 1 1 d . . . . .
H4A H 1.4663 0.5382 0.9246 0.024 Uiso 1 1 calc R . . . .
H4B H 1.2989 0.6335 0.9776 0.024 Uiso 1 1 calc R . . . .
C11 C 0.0266(3) 0.15899(14) 0.63314(12) 0.0199(3) Uani 1 1 d . . . . .
C10 C 0.2601(3) 0.23856(14) 0.68215(12) 0.0194(3) Uani 1 1 d . . . . .
H10 H 0.3164 0.2439 0.7560 0.023 Uiso 1 1 calc R . . . .
C2 C 0.6564(3) 0.39589(14) 0.68485(12) 0.0181(3) Uani 1 1 d . . . . .
C14 C 0.3268(3) 0.30175(14) 0.51541(12) 0.0204(3) Uani 1 1 d . . . . .
H14 H 0.4288 0.3505 0.4747 0.024 Uiso 1 1 calc R . . . .
C5 C 1.7069(3) 0.70515(15) 0.99087(12) 0.0225(4) Uani 1 1 d . . . . .
H5A H 1.7421 0.6880 1.0633 0.027 Uiso 1 1 calc R . . . .
H5B H 1.8577 0.6884 0.9504 0.027 Uiso 1 1 calc R . . . .
C8 C 1.3608(3) 0.78299(14) 0.83357(13) 0.0225(4) Uani 1 1 d . . . . .
H8A H 1.2094 0.7994 0.8738 0.027 Uiso 1 1 calc R . . . .
H8B H 1.3262 0.7999 0.7610 0.027 Uiso 1 1 calc R . . . .
C12 C -0.0581(3) 0.15036(14) 0.52509(12) 0.0220(4) Uani 1 1 d . . . . .
H12 H -0.2179 0.0960 0.4914 0.026 Uiso 1 1 calc R . . . .
C7 C 1.6205(3) 0.86472(15) 0.89118(13) 0.0244(4) Uani 1 1 d . . . . .
H7A H 1.6008 0.9495 0.9001 0.029 Uiso 1 1 calc R . . . .
H7B H 1.7680 0.8544 0.8468 0.029 Uiso 1 1 calc R . . . .
C13 C 0.0940(3) 0.22217(15) 0.46758(12) 0.0226(4) Uani 1 1 d . . . . .
H13 H 0.0374 0.2167 0.3938 0.027 Uiso 1 1 calc R . . . .
C15 C -0.1261(4) 0.08177(15) 0.69881(13) 0.0240(4) Uani 1 1 d . . . . .
C6 C 1.6924(4) 0.83702(15) 1.00095(13) 0.0269(4) Uani 1 1 d . . . . .
H6A H 1.8677 0.8878 1.0339 0.032 Uiso 1 1 calc R . . . .
H6B H 1.5555 0.8562 1.0483 0.032 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
F3 C15 1.343(2) . ?
F2 C15 1.340(2) . ?
F1 C15 1.3382(19) . ?
O1 C1 1.2305(19) . ?
O2 C2 1.2256(18) . ?
N1 C1 1.407(2) . ?
N1 C2 1.369(2) . ?
N2 C3 1.4659(19) . ?
N2 C1 1.3275(19) . ?
C3 C4 1.5196(19) . ?
C3 C8 1.522(2) . ?
C9 C10 1.388(2) . ?
C9 C2 1.500(2) . ?
C9 C14 1.397(2) . ?
C4 C5 1.525(2) . ?
C11 C10 1.388(2) . ?
C11 C12 1.392(2) . ?
C11 C15 1.494(2) . ?
C14 C13 1.382(2) . ?
C5 C6 1.522(2) . ?
C8 C7 1.523(2) . ?
C12 C13 1.382(2) . ?
C7 C6 1.525(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
C2 N1 C1 126.87(12) . . ?
C1 N2 C3 122.51(13) . . ?
N2 C3 C4 108.39(12) . . ?
N2 C3 C8 112.34(13) . . ?
C4 C3 C8 111.36(13) . . ?
O1 C1 N1 118.76(13) . . ?
O1 C1 N2 123.80(15) . . ?
N2 C1 N1 117.44(14) . . ?
C10 C9 C2 116.28(13) . . ?
C10 C9 C14 119.26(15) . . ?
C14 C9 C2 124.44(14) . . ?
C3 C4 C5 110.74(13) . . ?
C10 C11 C12 120.40(15) . . ?
C10 C11 C15 118.22(13) . . ?
C12 C11 C15 121.37(14) . . ?
C11 C10 C9 120.34(13) . . ?
O2 C2 N1 122.85(15) . . ?
O2 C2 C9 119.82(14) . . ?
N1 C2 C9 117.32(12) . . ?
C13 C14 C9 119.83(15) . . ?
C6 C5 C4 111.47(13) . . ?
C3 C8 C7 110.61(13) . . ?
C13 C12 C11 118.94(15) . . ?
C8 C7 C6 111.68(14) . . ?
C14 C13 C12 121.23(14) . . ?
F3 C15 C11 111.36(14) . . ?
F2 C15 F3 106.02(13) . . ?
F2 C15 C11 112.26(14) . . ?
F1 C15 F3 106.57(13) . . ?
F1 C15 F2 106.83(14) . . ?
F1 C15 C11 113.34(13) . . ?
C5 C6 C7 110.68(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_10
_database_code_depnum_ccdc_archive 'CCDC 1938715'
loop_
_audit_author_name
_audit_author_address
'Vitalii Suslonov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-12-16 downloaded from the CCDC.
;
_audit_creation_date             2019-07-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 N2 O2'
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H12O2N2F6
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                   5.3129(5)
_cell_length_b                   9.3886(7)
_cell_length_c                   12.8335(8)
_cell_angle_alpha                86.747(5)
_cell_angle_beta                 88.785(7)
_cell_angle_gamma                75.123(8)
_cell_volume                     617.68(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1735
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.0430
_cell_measurement_theta_min      3.7800
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93813
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5736
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.683
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -44.00   38.00   1.0000    7.3800
omega____ theta____ kappa____ phi______ frames
    -      -25.4311   57.0000   60.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega  -81.00  -13.00   1.0000    7.3800
omega____ theta____ kappa____ phi______ frames
    -      -25.4311  130.0000   63.0000 68

#__ type_ start__ end____ width___ exp.time_
  3 omega  -89.00  -45.00   1.0000    7.3800
omega____ theta____ kappa____ phi______ frames
    -      -25.4311  140.0000 -122.0000 44

#__ type_ start__ end____ width___ exp.time_
  4 omega  -92.00   -8.00   1.0000    7.3800
omega____ theta____ kappa____ phi______ frames
    -      -25.4311  -57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega  -95.00    9.00   1.0000    7.3800
omega____ theta____ kappa____ phi______ frames
    -      -25.4311  -19.0000 -120.0000 104

#__ type_ start__ end____ width___ exp.time_
  6 omega  -57.00    5.00   1.0000    7.3800
omega____ theta____ kappa____ phi______ frames
    -      -25.4311  -77.0000   90.0000 62

#__ type_ start__ end____ width___ exp.time_
  7 omega   -4.00   21.00   1.0000    7.3800
omega____ theta____ kappa____ phi______ frames
    -       26.3686   77.0000  -60.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0608304000
_diffrn_orient_matrix_UB_12      0.0049593000
_diffrn_orient_matrix_UB_13      -0.0492135000
_diffrn_orient_matrix_UB_21      0.1220097000
_diffrn_orient_matrix_UB_22      -0.0060041000
_diffrn_orient_matrix_UB_23      -0.0252903000
_diffrn_orient_matrix_UB_31      0.0222629000
_diffrn_orient_matrix_UB_32      -0.0778913000
_diffrn_orient_matrix_UB_33      0.0017699000
_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                2229
_reflns_number_total             2821
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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    ?
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2821
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.027
_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)+(0.0406P)²+0.1380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1036
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C5(H5), C9(H9), C11(H11), C6(H6), C15(H15), C8(H8), C13(H13),
 C7(H7), C12(H12), C14(H14)
;
_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
O2 O -0.03168(19) 0.77016(11) 0.01441(8) 0.0199(2) Uani 1 1 d . . . . .
O1 O 0.4923(2) 0.94498(11) 0.16527(8) 0.0204(2) Uani 1 1 d . . . . .
N2 N 0.0644(2) 0.94215(12) 0.16462(9) 0.0165(3) Uani 1 1 d . . . . .
H2 H -0.0608 0.9208 0.1298 0.020 Uiso 1 1 calc R . . . .
N1 N 0.3578(2) 0.82747(12) 0.03590(9) 0.0158(3) Uani 1 1 d . . . . .
H1 H 0.5116 0.8198 0.0065 0.019 Uiso 1 1 calc R . . . .
C1 C 0.3087(3) 0.90915(14) 0.12662(11) 0.0152(3) Uani 1 1 d . . . . .
C2 C 0.1971(3) 0.75853(14) -0.01241(11) 0.0155(3) Uani 1 1 d . . . . .
C10 C 0.3203(3) 0.66298(14) -0.09933(11) 0.0163(3) Uani 1 1 d . . . . .
C4 C 0.0611(3) 0.90377(14) 0.35748(11) 0.0167(3) Uani 1 1 d . . . . .
C3 C 0.0058(3) 1.01380(14) 0.26421(11) 0.0173(3) Uani 1 1 d . . . . .
H3A H -0.1801 1.0688 0.2656 0.021 Uiso 1 1 calc R . . . .
H3B H 0.1116 1.0858 0.2695 0.021 Uiso 1 1 calc R . . . .
C5 C -0.0901(3) 0.80250(15) 0.37420(11) 0.0189(3) Uani 1 1 d . . . . .
H5 H -0.2262 0.8034 0.3271 0.023 Uiso 1 1 calc R . . . .
C9 C 0.2585(3) 0.90139(15) 0.42780(11) 0.0198(3) Uani 1 1 d . . . . .
H9 H 0.3629 0.9694 0.4174 0.024 Uiso 1 1 calc R . . . .
C11 C 0.5286(3) 0.68744(16) -0.15965(11) 0.0204(3) Uani 1 1 d . . . . .
H11 H 0.5993 0.7680 -0.1467 0.025 Uiso 1 1 calc R . . . .
C6 C -0.0433(3) 0.70035(16) 0.45910(12) 0.0233(3) Uani 1 1 d . . . . .
H6 H -0.1460 0.6314 0.4693 0.028 Uiso 1 1 calc R . . . .
C15 C 0.2176(3) 0.54429(15) -0.11902(11) 0.0208(3) Uani 1 1 d . . . . .
H15 H 0.0730 0.5286 -0.0794 0.025 Uiso 1 1 calc R . . . .
C8 C 0.3038(3) 0.80015(16) 0.51319(12) 0.0235(3) Uani 1 1 d . . . . .
H8 H 0.4380 0.8001 0.5610 0.028 Uiso 1 1 calc R . . . .
C13 C 0.5334(3) 0.47341(16) -0.25656(12) 0.0257(4) Uani 1 1 d . . . . .
H13 H 0.6070 0.4084 -0.3096 0.031 Uiso 1 1 calc R . . . .
C7 C 0.1542(3) 0.69930(16) 0.52898(12) 0.0244(3) Uani 1 1 d . . . . .
H7 H 0.1863 0.6300 0.5871 0.029 Uiso 1 1 calc R . . . .
C12 C 0.6328(3) 0.59338(17) -0.23892(12) 0.0257(4) Uani 1 1 d . . . . .
H12 H 0.7720 0.6113 -0.2810 0.031 Uiso 1 1 calc R . . . .
C14 C 0.3271(3) 0.44897(16) -0.19672(12) 0.0253(4) Uani 1 1 d . . . . .
H14 H 0.2599 0.3668 -0.2087 0.030 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
O2 C2 1.2353(17) . ?
O1 C1 1.2321(17) . ?
N2 C1 1.3423(18) . ?
N2 C3 1.4685(17) . ?
N1 C1 1.4133(17) . ?
N1 C2 1.3728(18) . ?
C2 C10 1.5029(19) . ?
C10 C11 1.397(2) . ?
C10 C15 1.398(2) . ?
C4 C3 1.5182(19) . ?
C4 C5 1.399(2) . ?
C4 C9 1.393(2) . ?
C5 C6 1.393(2) . ?
C9 C8 1.392(2) . ?
C11 C12 1.396(2) . ?
C6 C7 1.392(2) . ?
C15 C14 1.394(2) . ?
C8 C7 1.388(2) . ?
C13 C12 1.392(2) . ?
C13 C14 1.384(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
C1 N2 C3 120.15(12) . . ?
C2 N1 C1 128.49(12) . . ?
O1 C1 N2 124.62(13) . . ?
O1 C1 N1 117.93(13) . . ?
N2 C1 N1 117.46(13) . . ?
O2 C2 N1 123.06(12) . . ?
O2 C2 C10 121.51(13) . . ?
N1 C2 C10 115.40(12) . . ?
C11 C10 C2 123.34(13) . . ?
C11 C10 C15 119.61(13) . . ?
C15 C10 C2 117.04(13) . . ?
C5 C4 C3 119.58(13) . . ?
C9 C4 C3 121.64(13) . . ?
C9 C4 C5 118.78(13) . . ?
N2 C3 C4 112.34(10) . . ?
C6 C5 C4 120.73(14) . . ?
C8 C9 C4 120.51(14) . . ?
C12 C11 C10 119.88(14) . . ?
C7 C6 C5 119.95(15) . . ?
C14 C15 C10 120.02(15) . . ?
C7 C8 C9 120.43(15) . . ?
C14 C13 C12 119.94(14) . . ?
C8 C7 C6 119.60(14) . . ?
C13 C12 C11 120.20(15) . . ?
C13 C14 C15 120.31(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
