# 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 2021

####################################################################### 
# 
# 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_dc
_database_code_depnum_ccdc_archive 'CCDC 2044826'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2021-02-15 deposited with the CCDC.	2021-02-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 Cl N3 O4'
_chemical_formula_sum            'C15 H14 Cl N3 O4'
_chemical_formula_weight         335.74

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.872(2)
_cell_length_b                   6.0495(4)
_cell_length_c                   16.2381(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.271(11)
_cell_angle_gamma                90.00
_cell_volume                     1496.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4027
_cell_measurement_theta_min      3.1663
_cell_measurement_theta_max      33.5438

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_min  0.76958
_exptl_absorpt_correction_T_max  1.24127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15847
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0899
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         29.58
_reflns_number_total             4123
_reflns_number_gt                1807
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0140P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4123
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0606
_refine_ls_wR_factor_gt          0.0568
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.17762(3) 0.24980(8) 0.04887(3) 0.06533(16) Uani 1 1 d . . .
N1 N 0.37773(9) 0.32901(18) 0.11231(8) 0.0355(3) Uani 1 1 d . . .
O1 O 0.56968(7) 0.85162(17) 0.22912(7) 0.0487(3) Uani 1 1 d . . .
C1 C 0.34770(10) 0.1358(2) 0.06390(9) 0.0336(4) Uani 1 1 d . . .
N2 N 0.45998(9) 0.3992(2) 0.11673(8) 0.0382(3) Uani 1 1 d . . .
C2 C 0.25994(11) 0.0841(3) 0.03140(10) 0.0412(4) Uani 1 1 d . . .
O2 O 0.62406(9) 0.6109(2) 0.15294(9) 0.0737(4) Uani 1 1 d . . .
O3 O 0.31687(8) 0.08304(18) 0.25049(7) 0.0552(3) Uani 1 1 d . . .
N3 N 0.41542(9) 0.3359(2) 0.32676(8) 0.0427(4) Uani 1 1 d . . .
C3 C 0.23376(12) -0.1039(3) -0.01795(10) 0.0519(5) Uani 1 1 d . . .
H3A H 0.1745 -0.1387 -0.0384 0.062 Uiso 1 1 calc R . .
O4 O 0.50107(8) 0.64145(19) 0.37122(7) 0.0582(4) Uani 1 1 d . . .
C4 C 0.29576(13) -0.2390(3) -0.03664(10) 0.0517(5) Uani 1 1 d . . .
H4A H 0.2784 -0.3651 -0.0698 0.062 Uiso 1 1 calc R . .
C5 C 0.38266(12) -0.1879(3) -0.00644(10) 0.0446(4) Uani 1 1 d . . .
H5A H 0.4245 -0.2778 -0.0198 0.053 Uiso 1 1 calc R . .
C6 C 0.40851(11) -0.0035(2) 0.04381(9) 0.0380(4) Uani 1 1 d . . .
H6A H 0.4680 0.0285 0.0648 0.046 Uiso 1 1 calc R . .
C7 C 0.35560(11) 0.2571(3) 0.25487(10) 0.0392(4) Uani 1 1 d . . .
C8 C 0.34790(11) 0.4225(2) 0.18330(10) 0.0358(4) Uani 1 1 d . . .
H8 H 0.2880(9) 0.4685(19) 0.1641(7) 0.025(4) Uiso 1 1 d . . .
C9 C 0.41684(11) 0.5974(3) 0.22114(10) 0.0366(4) Uani 1 1 d . . .
H9 H 0.3959(9) 0.739(2) 0.2137(8) 0.043(5) Uiso 1 1 d . . .
C10 C 0.45047(11) 0.5392(3) 0.31496(10) 0.0391(4) Uani 1 1 d . . .
C11 C 0.43930(13) 0.2185(3) 0.40819(10) 0.0631(6) Uani 1 1 d . . .
H11A H 0.3873 0.1871 0.4253 0.095 Uiso 1 1 calc R . .
H11B H 0.4783 0.3084 0.4511 0.095 Uiso 1 1 calc R . .
H11C H 0.4680 0.0824 0.4020 0.095 Uiso 1 1 calc R . .
C12 C 0.48341(10) 0.5520(2) 0.17349(10) 0.0352(4) Uani 1 1 d . . .
C13 C 0.56687(12) 0.6688(3) 0.18284(10) 0.0431(4) Uani 1 1 d . . .
C14 C 0.64931(12) 0.9829(3) 0.24661(11) 0.0555(5) Uani 1 1 d . . .
H14A H 0.6538 1.0545 0.1945 0.067 Uiso 1 1 calc R . .
H14B H 0.7004 0.8895 0.2682 0.067 Uiso 1 1 calc R . .
C15 C 0.64456(12) 1.1506(3) 0.31159(11) 0.0619(5) Uani 1 1 d . . .
H15A H 0.6972 1.2379 0.3258 0.093 Uiso 1 1 calc R . .
H15B H 0.6387 1.0779 0.3622 0.093 Uiso 1 1 calc R . .
H15C H 0.5947 1.2446 0.2889 0.093 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
Cl1 C2 1.7322(16) . ?
N1 N2 1.3555(16) . ?
N1 C1 1.4145(17) . ?
N1 C8 1.4759(18) . ?
O1 C13 1.3308(18) . ?
O1 C14 1.4517(18) . ?
C1 C2 1.380(2) . ?
C1 C6 1.387(2) . ?
N2 C12 1.2846(17) . ?
C2 C3 1.386(2) . ?
O2 C13 1.1957(18) . ?
O3 C7 1.2115(16) . ?
N3 C7 1.3675(19) . ?
N3 C10 1.3852(18) . ?
N3 C11 1.4545(18) . ?
C3 C4 1.377(2) . ?
C3 H3A 0.9300 . ?
O4 C10 1.2047(17) . ?
C4 C5 1.364(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.3748(19) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.512(2) . ?
C8 C9 1.523(2) . ?
C8 H8 0.956(12) . ?
C9 C12 1.500(2) . ?
C9 C10 1.508(2) . ?
C9 H9 0.914(13) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.471(2) . ?
C14 C15 1.481(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
N2 N1 C1 117.25(12) . . ?
N2 N1 C8 110.70(11) . . ?
C1 N1 C8 128.22(12) . . ?
C13 O1 C14 117.05(13) . . ?
C2 C1 C6 117.79(14) . . ?
C2 C1 N1 123.14(14) . . ?
C6 C1 N1 118.98(14) . . ?
C12 N2 N1 110.15(13) . . ?
C1 C2 C3 120.94(16) . . ?
C1 C2 Cl1 122.19(13) . . ?
C3 C2 Cl1 116.87(14) . . ?
C7 N3 C10 113.63(14) . . ?
C7 N3 C11 123.22(14) . . ?
C10 N3 C11 123.15(13) . . ?
C4 C3 C2 119.83(17) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C5 C4 C3 119.96(16) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 120.07(17) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C5 C6 C1 121.39(16) . . ?
C5 C6 H6A 119.3 . . ?
C1 C6 H6A 119.3 . . ?
O3 C7 N3 124.92(15) . . ?
O3 C7 C8 126.84(15) . . ?
N3 C7 C8 108.24(14) . . ?
N1 C8 C7 111.86(12) . . ?
N1 C8 C9 103.30(13) . . ?
C7 C8 C9 104.80(13) . . ?
N1 C8 H8 111.4(7) . . ?
C7 C8 H8 107.6(8) . . ?
C9 C8 H8 117.8(7) . . ?
C12 C9 C10 112.17(14) . . ?
C12 C9 C8 101.24(12) . . ?
C10 C9 C8 104.84(13) . . ?
C12 C9 H9 112.7(9) . . ?
C10 C9 H9 111.4(9) . . ?
C8 C9 H9 113.9(9) . . ?
O4 C10 N3 124.01(15) . . ?
O4 C10 C9 128.17(15) . . ?
N3 C10 C9 107.77(13) . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 119.40(15) . . ?
N2 C12 C9 113.44(14) . . ?
C13 C12 C9 127.09(14) . . ?
O2 C13 O1 124.31(16) . . ?
O2 C13 C12 125.56(16) . . ?
O1 C13 C12 110.13(15) . . ?
O1 C14 C15 107.39(15) . . ?
O1 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
O1 C14 H14B 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
N2 N1 C1 C2 -158.97(14) . . . . ?
C8 N1 C1 C2 45.3(2) . . . . ?
N2 N1 C1 C6 17.44(18) . . . . ?
C8 N1 C1 C6 -138.30(15) . . . . ?
C1 N1 N2 C12 -169.35(12) . . . . ?
C8 N1 N2 C12 -9.53(16) . . . . ?
C6 C1 C2 C3 1.5(2) . . . . ?
N1 C1 C2 C3 177.97(13) . . . . ?
C6 C1 C2 Cl1 -177.79(11) . . . . ?
N1 C1 C2 Cl1 -1.3(2) . . . . ?
C1 C2 C3 C4 -1.5(2) . . . . ?
Cl1 C2 C3 C4 177.88(13) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C4 C5 C6 C1 -1.0(2) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
N1 C1 C6 C5 -176.91(13) . . . . ?
C10 N3 C7 O3 179.97(15) . . . . ?
C11 N3 C7 O3 -0.7(2) . . . . ?
C10 N3 C7 C8 0.68(17) . . . . ?
C11 N3 C7 C8 -179.96(14) . . . . ?
N2 N1 C8 C7 -101.01(15) . . . . ?
C1 N1 C8 C7 56.0(2) . . . . ?
N2 N1 C8 C9 11.18(15) . . . . ?
C1 N1 C8 C9 168.19(14) . . . . ?
O3 C7 C8 N1 -63.3(2) . . . . ?
N3 C7 C8 N1 115.96(14) . . . . ?
O3 C7 C8 C9 -174.57(15) . . . . ?
N3 C7 C8 C9 4.71(16) . . . . ?
N1 C8 C9 C12 -8.27(15) . . . . ?
C7 C8 C9 C12 109.00(13) . . . . ?
N1 C8 C9 C10 -125.05(13) . . . . ?
C7 C8 C9 C10 -7.79(16) . . . . ?
C7 N3 C10 O4 176.42(15) . . . . ?
C11 N3 C10 O4 -2.9(2) . . . . ?
C7 N3 C10 C9 -5.90(18) . . . . ?
C11 N3 C10 C9 174.74(15) . . . . ?
C12 C9 C10 O4 77.0(2) . . . . ?
C8 C9 C10 O4 -174.02(16) . . . . ?
C12 C9 C10 N3 -100.59(15) . . . . ?
C8 C9 C10 N3 8.42(17) . . . . ?
N1 N2 C12 C13 -173.66(13) . . . . ?
N1 N2 C12 C9 3.53(17) . . . . ?
C10 C9 C12 N2 114.76(15) . . . . ?
C8 C9 C12 N2 3.48(17) . . . . ?
C10 C9 C12 C13 -68.30(19) . . . . ?
C8 C9 C12 C13 -179.58(14) . . . . ?
C14 O1 C13 O2 -2.5(2) . . . . ?
C14 O1 C13 C12 178.13(13) . . . . ?
N2 C12 C13 O2 -14.0(2) . . . . ?
C9 C12 C13 O2 169.18(17) . . . . ?
N2 C12 C13 O1 165.34(13) . . . . ?
C9 C12 C13 O1 -11.4(2) . . . . ?
C13 O1 C14 C15 -169.41(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        29.58
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_dc_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2044827'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2021-02-15 deposited with the CCDC.	2021-02-22 downloaded from the CCDC.
;
_audit_creation_date             2021-02-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 N2 O'
_chemical_formula_sum            'C16 H18 N2 O'
_chemical_formula_weight         254.32
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.5162(17)
_cell_length_b                   7.2314(9)
_cell_length_c                   16.393(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.819(14)
_cell_angle_gamma                90
_cell_volume                     1358.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1288
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      3.08
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?

_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             544
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8074
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.285
_diffrn_reflns_theta_min         3.081
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1288
_reflns_number_total             3358
_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_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.742
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      0.742
_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)+(0.0606P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1056
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B)
2.c Me refined with riding coordinates:
 C16(H16A,H16B,H16C)
2.d Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.64612(10) 0.06924(16) 0.38220(7) 0.0542(3) Uani 1 1 d . . . . .
O1 O 1.03527(8) 0.08525(15) 0.41544(7) 0.0708(4) Uani 1 1 d . . . . .
C1 C 0.67156(12) 0.2136(2) 0.44430(9) 0.0552(4) Uani 1 1 d . . . . .
H1 H 0.636849 0.185936 0.495085 0.066 Uiso 1 1 calc R U . . .
N2 N 0.74240(10) -0.01091(16) 0.35823(7) 0.0531(3) Uani 1 1 d . . . . .
C3 C 0.83394(12) 0.06399(19) 0.39736(9) 0.0496(4) Uani 1 1 d . . . . .
C4 C 0.80672(13) 0.2115(2) 0.45700(11) 0.0567(4) Uani 1 1 d . . . . .
C5 C 0.83897(15) 0.4089(2) 0.43470(11) 0.0659(5) Uani 1 1 d . . . . .
C6 C 0.80482(16) 0.5370(3) 0.50244(12) 0.0929(6) Uani 1 1 d . . . . .
H6A H 0.836801 0.659968 0.497092 0.111 Uiso 1 1 calc R U . . .
H6B H 0.831186 0.488357 0.556294 0.111 Uiso 1 1 calc R U . . .
C7 C 0.67016(16) 0.5389(2) 0.48770(11) 0.0844(6) Uani 1 1 d . . . . .
H7A H 0.635490 0.492875 0.535260 0.101 Uiso 1 1 calc R U . . .
H7B H 0.641168 0.662599 0.475112 0.101 Uiso 1 1 calc R U . . .
C8 C 0.64410(14) 0.4099(2) 0.41432(10) 0.0588(4) Uani 1 1 d . . . . .
C9 C 0.74563(13) 0.4509(2) 0.36475(10) 0.0656(5) Uani 1 1 d . . . . .
H9A H 0.748620 0.367996 0.318499 0.079 Uiso 1 1 calc R U . . .
H9B H 0.747107 0.578540 0.346663 0.079 Uiso 1 1 calc R U . . .
C10 C 0.53501(12) 0.00702(19) 0.35282(9) 0.0469(4) Uani 1 1 d . . . . .
C11 C 0.51998(13) -0.1236(2) 0.29149(11) 0.0699(5) Uani 1 1 d . . . . .
H11 H 0.584455 -0.173903 0.269714 0.084 Uiso 1 1 calc R U . . .
C12 C 0.40967(15) -0.1790(3) 0.26274(13) 0.0934(6) Uani 1 1 d . . . . .
H12 H 0.399977 -0.266016 0.220848 0.112 Uiso 1 1 calc R U . . .
C13 C 0.31406(15) -0.1093(3) 0.29417(12) 0.0838(6) Uani 1 1 d . . . . .
H13 H 0.239706 -0.148996 0.274334 0.101 Uiso 1 1 calc R U . . .
C14 C 0.32827(13) 0.0185(2) 0.35469(11) 0.0657(5) Uani 1 1 d . . . . .
H14 H 0.263256 0.066428 0.376669 0.079 Uiso 1 1 calc R U . . .
C15 C 0.43774(12) 0.0780(2) 0.38386(9) 0.0574(4) Uani 1 1 d . . . . .
H15 H 0.446305 0.167073 0.424960 0.069 Uiso 1 1 calc R U . . .
C16 C 0.96506(14) -0.1544(2) 0.32636(11) 0.0783(5) Uani 1 1 d . . . . .
H16A H 0.889652 -0.201146 0.305894 0.117 Uiso 1 1 calc R U . . .
H16B H 1.005811 -0.114124 0.281290 0.117 Uiso 1 1 calc R U . . .
H16C H 1.008974 -0.250434 0.355842 0.117 Uiso 1 1 calc R U . . .
C2 C 0.95065(12) 0.0046(2) 0.38240(9) 0.0541(4) Uani 1 1 d . . . . .
H8 H 0.5656(11) 0.4233(17) 0.3844(7) 0.052(4) Uiso 1 1 d . . . . .
H5 H 0.9176(13) 0.4191(18) 0.4204(8) 0.060(4) Uiso 1 1 d . . . . .
H4 H 0.8390(12) 0.1716(18) 0.5107(9) 0.060(4) Uiso 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
N1 C1 1.4667(17) . ?
N1 N2 1.3446(15) . ?
N1 C10 1.3953(16) . ?
O1 C2 1.2149(16) . ?
C1 H1 0.9800 . ?
C1 C4 1.549(2) . ?
C1 C8 1.525(2) . ?
N2 C3 1.2958(17) . ?
C3 C4 1.501(2) . ?
C3 C2 1.4553(19) . ?
C4 C5 1.529(2) . ?
C4 H4 0.965(14) . ?
C5 C6 1.528(2) . ?
C5 C9 1.521(2) . ?
C5 H5 0.961(14) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.545(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.528(2) . ?
C8 C9 1.519(2) . ?
C8 H8 0.988(12) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.377(2) . ?
C10 C15 1.3758(19) . ?
C11 H11 0.9300 . ?
C11 C12 1.369(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.359(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.354(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.371(2) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C2 1.492(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
N2 N1 C1 113.39(11) . . ?
N2 N1 C10 120.97(12) . . ?
C10 N1 C1 125.50(12) . . ?
N1 C1 H1 112.0 . . ?
N1 C1 C4 102.34(11) . . ?
N1 C1 C8 114.74(12) . . ?
C4 C1 H1 112.0 . . ?
C8 C1 H1 112.0 . . ?
C8 C1 C4 103.01(12) . . ?
C3 N2 N1 109.19(12) . . ?
N2 C3 C4 113.98(13) . . ?
N2 C3 C2 120.81(14) . . ?
C2 C3 C4 125.22(13) . . ?
C1 C4 H4 114.5(8) . . ?
C3 C4 C1 101.10(12) . . ?
C3 C4 C5 115.84(14) . . ?
C3 C4 H4 107.2(8) . . ?
C5 C4 C1 102.94(13) . . ?
C5 C4 H4 114.7(8) . . ?
C4 C5 C6 107.79(15) . . ?
C4 C5 H5 112.8(8) . . ?
C6 C5 H5 116.7(8) . . ?
C9 C5 C4 101.34(12) . . ?
C9 C5 C6 102.28(14) . . ?
C9 C5 H5 114.3(8) . . ?
C5 C6 H6A 111.2 . . ?
C5 C6 H6B 111.2 . . ?
C5 C6 C7 102.70(13) . . ?
H6A C6 H6B 109.1 . . ?
C7 C6 H6A 111.2 . . ?
C7 C6 H6B 111.2 . . ?
C6 C7 H7A 111.1 . . ?
C6 C7 H7B 111.1 . . ?
H7A C7 H7B 109.0 . . ?
C8 C7 C6 103.40(14) . . ?
C8 C7 H7A 111.1 . . ?
C8 C7 H7B 111.1 . . ?
C1 C8 C7 107.26(13) . . ?
C1 C8 H8 113.6(8) . . ?
C7 C8 H8 115.3(7) . . ?
C9 C8 C1 102.03(12) . . ?
C9 C8 C7 101.63(13) . . ?
C9 C8 H8 115.5(8) . . ?
C5 C9 C8 94.66(14) . . ?
C5 C9 H9A 112.8 . . ?
C5 C9 H9B 112.8 . . ?
C8 C9 H9A 112.8 . . ?
C8 C9 H9B 112.8 . . ?
H9A C9 H9B 110.3 . . ?
C11 C10 N1 121.06(13) . . ?
C15 C10 N1 120.30(14) . . ?
C15 C10 C11 118.63(13) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.69(15) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.35(17) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.25(16) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.54(15) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.54(15) . . ?
C14 C15 H15 119.7 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C2 C16 H16A 109.5 . . ?
C2 C16 H16B 109.5 . . ?
C2 C16 H16C 109.5 . . ?
O1 C2 C3 119.74(14) . . ?
O1 C2 C16 120.68(14) . . ?
C3 C2 C16 119.57(13) . . ?

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 C1 C4 C3 0.71(14) . . . . ?
N1 C1 C4 C5 120.76(13) . . . . ?
N1 C1 C8 C7 177.23(13) . . . . ?
N1 C1 C8 C9 -76.38(15) . . . . ?
N1 N2 C3 C4 0.86(17) . . . . ?
N1 N2 C3 C2 -179.23(12) . . . . ?
N1 C10 C11 C12 -178.61(15) . . . . ?
N1 C10 C15 C14 179.42(13) . . . . ?
C1 N1 N2 C3 -0.31(16) . . . . ?
C1 N1 C10 C11 176.94(14) . . . . ?
C1 N1 C10 C15 -1.9(2) . . . . ?
C1 C4 C5 C6 70.77(16) . . . . ?
C1 C4 C5 C9 -36.22(16) . . . . ?
C1 C8 C9 C5 -55.40(14) . . . . ?
N2 N1 C1 C4 -0.31(16) . . . . ?
N2 N1 C1 C8 110.44(14) . . . . ?
N2 N1 C10 C11 -7.5(2) . . . . ?
N2 N1 C10 C15 173.61(13) . . . . ?
N2 C3 C4 C1 -1.00(17) . . . . ?
N2 C3 C4 C5 -111.40(15) . . . . ?
N2 C3 C2 O1 174.89(13) . . . . ?
N2 C3 C2 C16 -4.9(2) . . . . ?
C3 C4 C5 C6 -179.92(13) . . . . ?
C3 C4 C5 C9 73.10(17) . . . . ?
C4 C1 C8 C7 -72.41(15) . . . . ?
C4 C1 C8 C9 33.97(15) . . . . ?
C4 C3 C2 O1 -5.2(2) . . . . ?
C4 C3 C2 C16 174.98(15) . . . . ?
C4 C5 C6 C7 -72.08(17) . . . . ?
C4 C5 C9 C8 56.10(14) . . . . ?
C5 C6 C7 C8 0.75(18) . . . . ?
C6 C5 C9 C8 -55.15(15) . . . . ?
C6 C7 C8 C1 71.20(17) . . . . ?
C6 C7 C8 C9 -35.47(17) . . . . ?
C7 C8 C9 C5 55.31(14) . . . . ?
C8 C1 C4 C3 -118.64(13) . . . . ?
C8 C1 C4 C5 1.41(15) . . . . ?
C9 C5 C6 C7 34.25(18) . . . . ?
C10 N1 C1 C4 175.51(13) . . . . ?
C10 N1 C1 C8 -73.73(17) . . . . ?
C10 N1 N2 C3 -176.34(12) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C10 C15 C14 0.5(2) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C10 -0.8(3) . . . . ?
C15 C10 C11 C12 0.3(2) . . . . ?
C2 C3 C4 C1 179.10(13) . . . . ?
C2 C3 C4 C5 68.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
