# 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_ksh_21
_database_code_depnum_ccdc_archive 'CCDC 2035579'
loop_
_audit_author_name
_audit_author_address
'Yu.V. Gatilov'
;Novosibirsk Institute of Organic Chemistry
Russia
;
_audit_update_record             
;
2020-10-06 deposited with the CCDC.	2021-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
1-(2,5-dimethyl-11,12-dihydro-5H-5,11-epoxybenzo[7,8]oxocino[4,3-b]pyridin-3-yl)ethan-1-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 N O3'
_chemical_formula_sum            'C18 H17 N O3'
_chemical_formula_weight         295.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7769(10)
_cell_length_b                   9.1976(12)
_cell_length_c                   10.1697(12)
_cell_angle_alpha                74.462(5)
_cell_angle_beta                 81.905(5)
_cell_angle_gamma                69.130(5)
_cell_volume                     738.13(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      29.17

_exptl_crystal_description       plate_thick
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8954
_exptl_absorpt_correction_T_max  0.9255
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25930
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.438
_diffrn_reflns_theta_max         29.188
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3979
_reflns_number_gt                3416
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0723P)²+0.2490P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3979
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_restrained_S_all      0.937
_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_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 0.56515(18) -0.44176(13) 0.64704(13) 0.0736(4) Uani 1 1 d . . . . .
N1 N 0.23112(11) 0.04305(11) 0.53705(9) 0.0317(2) Uani 1 1 d . . . . .
C2 C 0.35327(13) -0.09444(13) 0.57777(11) 0.0309(2) Uani 1 1 d . . . . .
C3 C 0.41916(13) -0.20367(12) 0.49395(11) 0.0312(2) Uani 1 1 d . . . . .
C4A C 0.21383(12) -0.03470(12) 0.33302(10) 0.0279(2) Uani 1 1 d . . . . .
C4 C 0.34845(13) -0.17132(12) 0.37043(11) 0.0304(2) Uani 1 1 d . . . . .
H4 H 0.391369 -0.241236 0.312881 0.037 Uiso 1 1 calc R U . . .
C5 C 0.12502(14) -0.00194(13) 0.20387(11) 0.0332(2) Uani 1 1 d . . . . .
O6 O 0.22895(11) 0.03672(10) 0.08579(8) 0.0384(2) Uani 1 1 d . . . . .
C6A C 0.24253(14) 0.18623(14) 0.06501(11) 0.0350(2) Uani 1 1 d . . . . .
C7 C 0.36445(17) 0.22076(17) -0.02831(13) 0.0455(3) Uani 1 1 d . . . . .
H7 H 0.432400 0.145222 -0.074945 0.055 Uiso 1 1 calc R U . . .
C8 C 0.38324(19) 0.3685(2) -0.05079(14) 0.0517(3) Uani 1 1 d . . . . .
H8 H 0.464555 0.392086 -0.112858 0.062 Uiso 1 1 calc R U . . .
C9 C 0.28263(19) 0.48185(18) 0.01787(14) 0.0508(3) Uani 1 1 d . . . . .
H9 H 0.297310 0.580361 0.003077 0.061 Uiso 1 1 calc R U . . .
C10A C 0.13774(14) 0.29993(13) 0.13282(11) 0.0347(2) Uani 1 1 d . . . . .
C10 C 0.15999(17) 0.44770(15) 0.10873(13) 0.0434(3) Uani 1 1 d . . . . .
H10 H 0.091654 0.524244 0.154211 0.052 Uiso 1 1 calc R U . . .
C11 C -0.00019(14) 0.26320(13) 0.22639(12) 0.0358(2) Uani 1 1 d . . . . .
H11 H -0.100337 0.355222 0.205404 0.043 Uiso 1 1 calc R U . . .
C12A C 0.16346(12) 0.07208(12) 0.41792(10) 0.0285(2) Uani 1 1 d . . . . .
C12 C 0.02831(14) 0.22875(13) 0.37714(12) 0.0353(2) Uani 1 1 d . . . . .
H12A H 0.057222 0.314056 0.394619 0.042 Uiso 1 1 calc R U . . .
H12B H -0.070995 0.224123 0.430991 0.042 Uiso 1 1 calc R U . . .
O13 O -0.02324(10) 0.12616(10) 0.20036(9) 0.0390(2) Uani 1 1 d . . . . .
C14 C 0.41476(17) -0.11971(17) 0.71558(13) 0.0437(3) Uani 1 1 d . . . . .
H14A H 0.378795 -0.019501 0.741868 0.066 Uiso 1 1 calc R U . . .
H14B H 0.531907 -0.161433 0.711192 0.066 Uiso 1 1 calc R U . . .
H14C H 0.372845 -0.194337 0.781699 0.066 Uiso 1 1 calc R U . . .
C15 C 0.56231(16) -0.35402(14) 0.53430(14) 0.0429(3) Uani 1 1 d . . . . .
C16 C 0.69972(18) -0.39023(19) 0.4303(2) 0.0615(4) Uani 1 1 d . . . . .
H16A H 0.789083 -0.480147 0.471836 0.092 Uiso 1 1 calc R U . . .
H16B H 0.734726 -0.298753 0.395436 0.092 Uiso 1 1 calc R U . . .
H16C H 0.663744 -0.415067 0.356700 0.092 Uiso 1 1 calc R U . . .
C17 C 0.08558(19) -0.14406(17) 0.18987(14) 0.0474(3) Uani 1 1 d . . . . .
H17A H 0.015400 -0.172957 0.266002 0.071 Uiso 1 1 calc R U . . .
H17B H 0.184776 -0.232823 0.188236 0.071 Uiso 1 1 calc R U . . .
H17C H 0.031507 -0.116651 0.106475 0.071 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 C15 1.2101(18) . ?
N1 C2 1.3411(14) . ?
N1 C12A 1.3447(13) . ?
C2 C3 1.4058(15) . ?
C2 C14 1.5028(15) . ?
C3 C4 1.3926(14) . ?
C3 C15 1.5042(15) . ?
C4A C4 1.3902(14) . ?
C4A C12A 1.3939(14) . ?
C4A C5 1.5272(14) . ?
C4 H4 0.9300 . ?
C5 O13 1.4075(14) . ?
C5 O6 1.4472(14) . ?
C5 C17 1.5115(16) . ?
O6 C6A 1.3798(14) . ?
C6A C10A 1.3920(17) . ?
C6A C7 1.3933(17) . ?
C7 C8 1.382(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.384(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(2) . ?
C9 H9 0.9300 . ?
C10A C10 1.3938(17) . ?
C10A C11 1.5099(16) . ?
C10 H10 0.9300 . ?
C11 O13 1.4406(15) . ?
C11 C12 1.5181(16) . ?
C11 H11 0.9800 . ?
C12A C12 1.5020(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.493(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C2 N1 C12A 119.35(9) . . ?
N1 C2 C3 121.16(9) . . ?
N1 C2 C14 115.37(10) . . ?
C3 C2 C14 123.46(10) . . ?
C4 C3 C2 118.65(9) . . ?
C4 C3 C15 119.38(10) . . ?
C2 C3 C15 121.96(10) . . ?
C4 C4A C12A 117.25(9) . . ?
C4 C4A C5 121.55(9) . . ?
C12A C4A C5 121.19(9) . . ?
C4A C4 C3 120.11(9) . . ?
C4A C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
O13 C5 O6 109.33(9) . . ?
O13 C5 C17 107.18(10) . . ?
O6 C5 C17 106.77(10) . . ?
O13 C5 C4A 111.17(9) . . ?
O6 C5 C4A 108.84(9) . . ?
C17 C5 C4A 113.40(9) . . ?
C6A O6 C5 113.73(8) . . ?
O6 C6A C10A 121.74(10) . . ?
O6 C6A C7 117.48(11) . . ?
C10A C6A C7 120.77(12) . . ?
C8 C7 C6A 119.24(13) . . ?
C8 C7 H7 120.4 . . ?
C6A C7 H7 120.4 . . ?
C7 C8 C9 120.85(13) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C10 119.59(13) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C6A C10A C10 118.75(11) . . ?
C6A C10A C11 119.64(10) . . ?
C10 C10A C11 121.57(11) . . ?
C9 C10 C10A 120.77(13) . . ?
C9 C10 H10 119.6 . . ?
C10A C10 H10 119.6 . . ?
O13 C11 C10A 108.98(9) . . ?
O13 C11 C12 108.52(9) . . ?
C10A C11 C12 113.72(9) . . ?
O13 C11 H11 108.5 . . ?
C10A C11 H11 108.5 . . ?
C12 C11 H11 108.5 . . ?
N1 C12A C4A 123.15(9) . . ?
N1 C12A C12 116.90(9) . . ?
C4A C12A C12 119.96(9) . . ?
C12A C12 C11 109.75(9) . . ?
C12A C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C12A C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C5 O13 C11 111.26(8) . . ?
C2 C14 H14A 109.5 . . ?
C2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 C16 121.60(13) . . ?
O1 C15 C3 120.91(13) . . ?
C16 C15 C3 117.49(11) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 C17 H17A 109.5 . . ?
C5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C12A N1 C2 C3 4.37(15) . . . . ?
C12A N1 C2 C14 -176.88(10) . . . . ?
N1 C2 C3 C4 -3.91(16) . . . . ?
C14 C2 C3 C4 177.45(10) . . . . ?
N1 C2 C3 C15 176.49(10) . . . . ?
C14 C2 C3 C15 -2.15(17) . . . . ?
C12A C4A C4 C3 5.18(15) . . . . ?
C5 C4A C4 C3 -175.19(9) . . . . ?
C2 C3 C4 C4A -1.04(16) . . . . ?
C15 C3 C4 C4A 178.57(10) . . . . ?
C4 C4A C5 O13 169.15(9) . . . . ?
C12A C4A C5 O13 -11.23(14) . . . . ?
C4 C4A C5 O6 -70.38(12) . . . . ?
C12A C4A C5 O6 109.24(11) . . . . ?
C4 C4A C5 C17 48.30(14) . . . . ?
C12A C4A C5 C17 -132.08(11) . . . . ?
O13 C5 O6 C6A 48.93(11) . . . . ?
C17 C5 O6 C6A 164.56(9) . . . . ?
C4A C5 O6 C6A -72.68(11) . . . . ?
C5 O6 C6A C10A -13.50(14) . . . . ?
C5 O6 C6A C7 167.31(10) . . . . ?
O6 C6A C7 C8 -179.25(11) . . . . ?
C10A C6A C7 C8 1.56(18) . . . . ?
C6A C7 C8 C9 -0.1(2) . . . . ?
C7 C8 C9 C10 -1.0(2) . . . . ?
O6 C6A C10A C10 178.96(10) . . . . ?
C7 C6A C10A C10 -1.88(16) . . . . ?
O6 C6A C10A C11 -3.16(16) . . . . ?
C7 C6A C10A C11 176.00(10) . . . . ?
C8 C9 C10 C10A 0.6(2) . . . . ?
C6A C10A C10 C9 0.77(18) . . . . ?
C11 C10A C10 C9 -177.06(11) . . . . ?
C6A C10A C11 O13 -15.00(13) . . . . ?
C10 C10A C11 O13 162.82(10) . . . . ?
C6A C10A C11 C12 106.20(12) . . . . ?
C10 C10A C11 C12 -75.99(13) . . . . ?
C2 N1 C12A C4A 0.12(16) . . . . ?
C2 N1 C12A C12 -179.42(9) . . . . ?
C4 C4A C12A N1 -4.89(15) . . . . ?
C5 C4A C12A N1 175.47(9) . . . . ?
C4 C4A C12A C12 174.63(9) . . . . ?
C5 C4A C12A C12 -5.00(15) . . . . ?
N1 C12A C12 C11 163.88(10) . . . . ?
C4A C12A C12 C11 -15.68(14) . . . . ?
O13 C11 C12 C12A 52.47(12) . . . . ?
C10A C11 C12 C12A -68.98(12) . . . . ?
O6 C5 O13 C11 -70.24(11) . . . . ?
C17 C5 O13 C11 174.39(9) . . . . ?
C4A C5 O13 C11 49.94(12) . . . . ?
C10A C11 O13 C5 51.03(11) . . . . ?
C12 C11 O13 C5 -73.29(11) . . . . ?
C4 C3 C15 O1 -131.31(14) . . . . ?
C2 C3 C15 O1 48.29(18) . . . . ?
C4 C3 C15 C16 48.71(16) . . . . ?
C2 C3 C15 C16 -131.70(13) . . . . ?

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.042



