# 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 2023

####################################################################### 
# 
# 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_2-25
_database_code_depnum_ccdc_archive 'CCDC 2263510'
loop_
_audit_author_name
_audit_author_address
'Yun Zhang'
;Zunyi university
China
;
_audit_update_record             
;
2023-05-17 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;
_audit_creation_date             2021-09-03
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 N2 O'
_chemical_formula_sum            'C17 H14 N2 O'
_chemical_formula_weight         262.30
_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 0.0033 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                   10.5549(9)
_cell_length_b                   14.5492(13)
_cell_length_c                   8.7409(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.492(6)
_cell_angle_gamma                90
_cell_volume                     1338.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2186
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      28.2920
_cell_measurement_theta_min      2.3920
_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  0.92138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5811
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.389
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  30.00   1.00    2.00    --  -11.27 -99.00-120.00   38
  2  ω    -25.00  92.00   1.00    2.00    --   11.90  19.00-150.00  117
  3  ω     56.00  95.00   1.00    2.00    --   11.90 178.00  60.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0154522000
_diffrn_orient_matrix_UB_12      0.0472611000
_diffrn_orient_matrix_UB_13      -0.0053513000
_diffrn_orient_matrix_UB_21      -0.0621784000
_diffrn_orient_matrix_UB_22      0.0092337000
_diffrn_orient_matrix_UB_23      -0.0331577000
_diffrn_orient_matrix_UB_31      -0.0207623000
_diffrn_orient_matrix_UB_32      0.0074896000
_diffrn_orient_matrix_UB_33      0.0742651000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1901
_reflns_number_total             2359
_reflns_odcompleteness_completeness 99.93
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.059
_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)+(0.0407P)²+0.1890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.1006
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.12672(10) 0.58696(8) 0.16385(12) 0.0287(3) Uani 1 1 d . . . . .
N1 N 0.30944(12) 0.52301(9) 0.26377(13) 0.0207(3) Uani 1 1 d . . . . .
N2 N 0.35171(14) 0.72566(11) 0.45309(18) 0.0397(4) Uani 1 1 d . . . . .
C1 C 0.51636(15) 0.59437(11) 0.20475(16) 0.0205(4) Uani 1 1 d . . . . .
C2 C 0.59056(16) 0.67166(12) 0.18438(18) 0.0289(4) Uani 1 1 d . . . . .
H2 H 0.554932 0.729879 0.190596 0.035 Uiso 1 1 calc R U . . .
C3 C 0.71664(16) 0.66289(13) 0.15499(19) 0.0318(4) Uani 1 1 d . . . . .
H3 H 0.765615 0.714907 0.140974 0.038 Uiso 1 1 calc R U . . .
C4 C 0.76964(16) 0.57627(13) 0.14654(18) 0.0304(4) Uani 1 1 d . . . . .
H4 H 0.854534 0.569787 0.127016 0.036 Uiso 1 1 calc R U . . .
C5 C 0.69631(16) 0.49971(13) 0.16711(17) 0.0273(4) Uani 1 1 d . . . . .
H5 H 0.732423 0.441678 0.160620 0.033 Uiso 1 1 calc R U . . .
C17 C 0.37664(15) 0.60745(11) 0.23012(17) 0.0207(4) Uani 1 1 d . . . . .
H17 H 0.335018 0.633438 0.135690 0.025 Uiso 1 1 calc R U . . .
C6 C 0.56887(15) 0.50733(12) 0.19752(15) 0.0214(4) Uani 1 1 d . . . . .
C7 C 0.49067(16) 0.42379(12) 0.22399(19) 0.0266(4) Uani 1 1 d . . . . .
H7A H 0.544817 0.376234 0.271558 0.032 Uiso 1 1 calc R U . . .
H7B H 0.454230 0.400576 0.126212 0.032 Uiso 1 1 calc R U . . .
C8 C 0.38502(15) 0.44541(12) 0.32607(17) 0.0238(4) Uani 1 1 d . . . . .
H8A H 0.330856 0.391958 0.333101 0.029 Uiso 1 1 calc R U . . .
H8B H 0.421175 0.460258 0.428527 0.029 Uiso 1 1 calc R U . . .
C9 C 0.18083(15) 0.52313(11) 0.23320(16) 0.0208(4) Uani 1 1 d . . . . .
C10 C 0.10686(15) 0.44459(11) 0.29171(16) 0.0209(4) Uani 1 1 d . . . . .
C11 C 0.11578(16) 0.42268(12) 0.44689(17) 0.0268(4) Uani 1 1 d . . . . .
H11 H 0.172996 0.453874 0.514582 0.032 Uiso 1 1 calc R U . . .
C12 C 0.03963(16) 0.35453(13) 0.50060(18) 0.0312(4) Uani 1 1 d . . . . .
H12 H 0.045079 0.340407 0.604677 0.037 Uiso 1 1 calc R U . . .
C13 C -0.04471(16) 0.30721(12) 0.40020(18) 0.0290(4) Uani 1 1 d . . . . .
H13 H -0.094883 0.260685 0.436378 0.035 Uiso 1 1 calc R U . . .
C14 C -0.05416(15) 0.32935(12) 0.24580(18) 0.0263(4) Uani 1 1 d . . . . .
H14 H -0.110839 0.297644 0.178165 0.032 Uiso 1 1 calc R U . . .
C15 C 0.02045(15) 0.39852(12) 0.19166(17) 0.0228(4) Uani 1 1 d . . . . .
H15 H 0.012600 0.414096 0.088163 0.027 Uiso 1 1 calc R U . . .
C16 C 0.36229(15) 0.67480(12) 0.35541(19) 0.0262(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.2254(18) . ?
N1 C17 1.4601(19) . ?
N1 C8 1.463(2) . ?
N1 C9 1.363(2) . ?
N2 C16 1.142(2) . ?
C1 C2 1.390(2) . ?
C1 C17 1.520(2) . ?
C1 C6 1.386(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.396(2) . ?
C17 H17 0.9800 . ?
C17 C16 1.486(2) . ?
C6 C7 1.497(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.515(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.497(2) . ?
C10 C11 1.389(2) . ?
C10 C15 1.386(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(2) . ?
C15 H15 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
C17 N1 C8 117.72(12) . . ?
C9 N1 C17 116.84(13) . . ?
C9 N1 C8 125.44(13) . . ?
C2 C1 C17 118.69(14) . . ?
C6 C1 C2 120.15(15) . . ?
C6 C1 C17 121.14(14) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.66(17) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.59(17) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.77(16) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.39(16) . . ?
C6 C5 H5 119.3 . . ?
N1 C17 C1 114.59(13) . . ?
N1 C17 H17 107.5 . . ?
N1 C17 C16 109.10(12) . . ?
C1 C17 H17 107.5 . . ?
C16 C17 C1 110.25(13) . . ?
C16 C17 H17 107.5 . . ?
C1 C6 C5 118.43(16) . . ?
C1 C6 C7 120.50(14) . . ?
C5 C6 C7 121.07(15) . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C6 C7 C8 111.25(14) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
N1 C8 C7 110.26(13) . . ?
N1 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
O1 C9 N1 121.10(15) . . ?
O1 C9 C10 120.82(14) . . ?
N1 C9 C10 118.05(14) . . ?
C11 C10 C9 120.77(14) . . ?
C15 C10 C9 119.26(13) . . ?
C15 C10 C11 119.74(15) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.98(15) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.27(15) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.77(16) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.23(15) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 119.99(14) . . ?
C14 C15 H15 120.0 . . ?
N2 C16 C17 179.09(19) . . ?

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
O1 C9 C10 C11 -121.72(17) . . . . ?
O1 C9 C10 C15 52.7(2) . . . . ?
N1 C9 C10 C11 56.1(2) . . . . ?
N1 C9 C10 C15 -129.47(16) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C1 C6 C7 C8 -26.9(2) . . . . ?
C2 C1 C17 N1 -174.85(13) . . . . ?
C2 C1 C17 C16 -51.33(18) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
C2 C1 C6 C7 178.17(14) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C4 C5 C6 C7 -178.33(14) . . . . ?
C5 C6 C7 C8 152.25(14) . . . . ?
C17 N1 C8 C7 -53.28(17) . . . . ?
C17 N1 C9 O1 8.5(2) . . . . ?
C17 N1 C9 C10 -169.30(12) . . . . ?
C17 C1 C2 C3 -177.44(14) . . . . ?
C17 C1 C6 C5 177.16(13) . . . . ?
C17 C1 C6 C7 -3.7(2) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C6 C1 C17 N1 6.96(19) . . . . ?
C6 C1 C17 C16 130.48(15) . . . . ?
C6 C7 C8 N1 53.63(17) . . . . ?
C8 N1 C17 C1 22.66(17) . . . . ?
C8 N1 C17 C16 -101.48(15) . . . . ?
C8 N1 C9 O1 -170.99(13) . . . . ?
C8 N1 C9 C10 11.2(2) . . . . ?
C9 N1 C17 C1 -156.91(12) . . . . ?
C9 N1 C17 C16 78.95(16) . . . . ?
C9 N1 C8 C7 126.25(15) . . . . ?
C9 C10 C11 C12 175.06(15) . . . . ?
C9 C10 C15 C14 -176.15(14) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C11 C10 C15 C14 -1.7(2) . . . . ?
C11 C12 C13 C14 -1.1(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C10 1.3(2) . . . . ?
C15 C10 C11 C12 0.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.751
####################################################################### 
# 
# 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_c1
_database_code_depnum_ccdc_archive 'CCDC 2263511'
loop_
_audit_author_name
_audit_author_address
'Yun Zhang'
;Zunyi university
China
;
_audit_update_record             
;
2023-05-17 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;
_audit_creation_date             2023-02-21
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 N2 O'
_chemical_formula_sum            'C12 H12 N2 O'
_chemical_formula_weight         200.24
_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 0.0033 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                   7.1562(12)
_cell_length_b                   8.1948(14)
_cell_length_c                   9.4259(17)
_cell_angle_alpha                102.299(15)
_cell_angle_beta                 97.775(15)
_cell_angle_gamma                99.273(14)
_cell_volume                     524.71(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1166
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      26.7510
_cell_measurement_theta_min      2.9030
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0899
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3302
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.246
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00  18.00   1.00    1.99    --  -11.27 -77.00-150.00   95
  2  ω    -54.00  35.00   1.00    1.99    --   11.90 -57.00 -30.00   89
  3  ω    -16.00  84.00   1.00    1.99    --   11.90  57.00 120.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0267095000
_diffrn_orient_matrix_UB_12      0.0528986000
_diffrn_orient_matrix_UB_13      0.0724910000
_diffrn_orient_matrix_UB_21      0.0549462000
_diffrn_orient_matrix_UB_22      0.0629253000
_diffrn_orient_matrix_UB_23      -0.0270227000
_diffrn_orient_matrix_UB_31      -0.0817050000
_diffrn_orient_matrix_UB_32      0.0374738000
_diffrn_orient_matrix_UB_33      -0.0116588000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1239
_reflns_number_total             1845
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.115(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1845
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      0.965
_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)+(0.0599P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1435
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.7384(2) 0.4716(2) 0.61828(19) 0.0432(5) Uani 1 1 d . . . . .
N1 N 0.2989(2) 0.0772(3) 0.4012(3) 0.0493(7) Uani 1 1 d . . . . .
N2 N 0.7618(2) 0.2697(2) 0.4221(2) 0.0290(5) Uani 1 1 d . . . . .
C1 C 0.7210(3) 0.2029(3) 0.1125(3) 0.0325(6) Uani 1 1 d . . . . .
C2 C 0.7110(3) 0.1878(3) -0.0373(3) 0.0428(7) Uani 1 1 d . . . . .
H2 H 0.810050 0.147292 -0.083869 0.051 Uiso 1 1 calc R U . . .
C3 C 0.5611(3) 0.2299(3) -0.1208(3) 0.0445(7) Uani 1 1 d . . . . .
H3 H 0.557642 0.219749 -0.223493 0.053 Uiso 1 1 calc R U . . .
C4 C 0.4160(3) 0.2870(3) -0.0541(3) 0.0424(7) Uani 1 1 d . . . . .
H4 H 0.311340 0.314640 -0.111583 0.051 Uiso 1 1 calc R U . . .
C5 C 0.4212(3) 0.3044(3) 0.0959(3) 0.0349(6) Uani 1 1 d . . . . .
H5 H 0.320948 0.343910 0.141438 0.042 Uiso 1 1 calc R U . . .
C6 C 0.5754(3) 0.2633(3) 0.1793(3) 0.0288(6) Uani 1 1 d . . . . .
C7 C 0.5795(2) 0.2908(3) 0.3441(2) 0.0287(6) Uani 1 1 d . . . . .
H7 H 0.562432 0.409807 0.383368 0.034 Uiso 1 1 calc R U . . .
C8 C 0.4196(3) 0.1712(3) 0.3767(3) 0.0343(6) Uani 1 1 d . . . . .
C9 C 0.8867(3) 0.1559(3) 0.2031(3) 0.0395(6) Uani 1 1 d . . . . .
H9A H 0.918893 0.051146 0.146068 0.047 Uiso 1 1 calc R U . . .
H9B H 1.001179 0.248517 0.222576 0.047 Uiso 1 1 calc R U . . .
C10 C 0.8382(3) 0.1269(3) 0.3480(3) 0.0336(6) Uani 1 1 d . . . . .
H10A H 0.741827 0.020202 0.329942 0.040 Uiso 1 1 calc R U . . .
H10B H 0.955202 0.115430 0.411297 0.040 Uiso 1 1 calc R U . . .
C11 C 0.8252(3) 0.3644(3) 0.5621(3) 0.0295(6) Uani 1 1 d . . . . .
C12 C 1.0062(3) 0.3349(3) 0.6463(3) 0.0407(7) Uani 1 1 d . . . . .
H12A H 1.047773 0.423894 0.738113 0.061 Uiso 1 1 calc R U . . .
H12B H 1.107596 0.338417 0.586138 0.061 Uiso 1 1 calc R U . . .
H12C H 0.981106 0.223209 0.669494 0.061 Uiso 1 1 calc R U . . .


_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 C11 1.227(3) . ?
N1 C8 1.144(3) . ?
N2 C7 1.463(2) . ?
N2 C10 1.455(3) . ?
N2 C11 1.356(3) . ?
C1 C2 1.382(3) . ?
C1 C6 1.393(3) . ?
C1 C9 1.515(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(3) . ?
C6 C7 1.517(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.492(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.511(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.507(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
C10 N2 C7 114.70(17) . . ?
C11 N2 C7 117.84(18) . . ?
C11 N2 C10 126.58(16) . . ?
C2 C1 C6 118.5(2) . . ?
C2 C1 C9 121.1(2) . . ?
C6 C1 C9 120.4(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.6(2) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 120.6(2) . . ?
C1 C6 C7 121.89(17) . . ?
C5 C6 C7 117.5(2) . . ?
N2 C7 C6 112.26(17) . . ?
N2 C7 H7 108.2 . . ?
N2 C7 C8 108.67(16) . . ?
C6 C7 H7 108.2 . . ?
C8 C7 C6 111.19(17) . . ?
C8 C7 H7 108.2 . . ?
N1 C8 C7 178.7(2) . . ?
C1 C9 H9A 109.3 . . ?
C1 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C1 111.71(18) . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
N2 C10 C9 109.65(17) . . ?
N2 C10 H10A 109.7 . . ?
N2 C10 H10B 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O1 C11 N2 120.98(18) . . ?
O1 C11 C12 121.0(2) . . ?
N2 C11 C12 118.0(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C1 C2 C3 C4 -0.7(4) . . . . ?
C1 C6 C7 N2 7.9(3) . . . . ?
C1 C6 C7 C8 -114.1(2) . . . . ?
C1 C9 C10 N2 -50.1(2) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
C2 C1 C6 C7 -177.41(19) . . . . ?
C2 C1 C9 C10 -161.4(2) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C5 C6 C7 177.67(18) . . . . ?
C5 C6 C7 N2 -170.74(16) . . . . ?
C5 C6 C7 C8 67.3(2) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C6 C1 C9 C10 18.9(3) . . . . ?
C7 N2 C10 C9 64.1(2) . . . . ?
C7 N2 C11 O1 -4.3(3) . . . . ?
C7 N2 C11 C12 176.13(17) . . . . ?
C9 C1 C2 C3 179.93(19) . . . . ?
C9 C1 C6 C5 -179.08(18) . . . . ?
C9 C1 C6 C7 2.3(3) . . . . ?
C10 N2 C7 C6 -41.6(2) . . . . ?
C10 N2 C7 C8 81.8(2) . . . . ?
C10 N2 C11 O1 -173.0(2) . . . . ?
C10 N2 C11 C12 7.5(3) . . . . ?
C11 N2 C7 C6 148.41(19) . . . . ?
C11 N2 C7 C8 -88.2(2) . . . . ?
C11 N2 C10 C9 -126.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 20.718
_oxdiff_exptl_absorpt_empirical_full_min 0.357
