# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 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_Lee-A
_database_code_depnum_ccdc_archive 'CCDC 2077448'
loop_
_audit_author_name
_audit_author_address
'Ha Jin Lee'
;Yeungnam University
South Korea
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
3-Methoxy-10,10-dimethyl-6,9,10,11-tetrahydrobenzo[c]acridin-8(5H)-one
_chemical_name_common            ?
_chemical_melting_point          441
_chemical_formula_moiety         'C20 H21 N O2'
_chemical_formula_sum            'C20 H21 N O2'
_chemical_formula_weight         307.38

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                   10.249(3)
_cell_length_b                   11.657(4)
_cell_length_c                   14.822(4)
_cell_angle_alpha                104.005(8)
_cell_angle_beta                 92.306(8)
_cell_angle_gamma                109.243(7)
_cell_volume                     1608.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    6474
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.03

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6305
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PHOTON III M14'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33055
_diffrn_reflns_av_unetI/netI     0.0950
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.922
_diffrn_reflns_theta_max         28.417
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7942
_reflns_number_gt                4218
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0891P)²+0.7672P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7942
_refine_ls_number_parameters     421
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1518
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.2295
_refine_ls_wR_factor_gt          0.1895
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.047
_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
C1 C 0.6605(3) 0.6734(3) -0.0173(2) 0.0392(7) Uani 1 1 d . . . . .
C2 C 0.5188(3) 0.6304(3) -0.0463(2) 0.0427(7) Uani 1 1 d . . . . .
H2 H 0.4748 0.5487 -0.0864 0.051 Uiso 1 1 calc R U . . .
C3 C 0.4413(3) 0.7064(3) -0.0170(2) 0.0378(7) Uani 1 1 d . . . . .
C4 C 0.5060(3) 0.8278(2) 0.04344(19) 0.0327(6) Uani 1 1 d . . . . .
C5 C 0.6485(3) 0.8681(3) 0.0725(2) 0.0359(6) Uani 1 1 d . . . . .
H5 H 0.6930 0.9489 0.1137 0.043 Uiso 1 1 calc R U . . .
C6 C 0.7261(3) 0.7926(3) 0.0424(2) 0.0389(7) Uani 1 1 d . . . . .
H6 H 0.8224 0.8220 0.0623 0.047 Uiso 1 1 calc R U . . .
C7 C 0.2863(3) 0.6605(3) -0.0471(3) 0.0514(9) Uani 1 1 d . . . . .
H7A H 0.2363 0.6258 0.0008 0.062 Uiso 1 1 calc R U . . .
H7B H 0.2616 0.5932 -0.1059 0.062 Uiso 1 1 calc R U . . .
C8 C 0.2434(3) 0.7690(3) -0.0607(2) 0.0440(7) Uani 1 1 d . . . . .
H8A H 0.2854 0.7972 -0.1133 0.053 Uiso 1 1 calc R U . . .
H8B H 0.1419 0.7399 -0.0757 0.053 Uiso 1 1 calc R U . . .
C9 C 0.2897(3) 0.8770(2) 0.0265(2) 0.0352(6) Uani 1 1 d . . . . .
C10 C 0.4232(3) 0.9089(2) 0.07395(19) 0.0314(6) Uani 1 1 d . . . . .
N1 N 0.4797(2) 1.0107(2) 0.14780(16) 0.0331(5) Uani 1 1 d . . . . .
C11 C 0.4041(3) 1.0839(2) 0.17738(19) 0.0323(6) Uani 1 1 d . . . . .
C12 C 0.2682(3) 1.0559(2) 0.1371(2) 0.0336(6) Uani 1 1 d . . . . .
C13 C 0.2130(3) 0.9514(3) 0.0597(2) 0.0384(7) Uani 1 1 d . . . . .
H13 H 0.1226 0.9316 0.0299 0.046 Uiso 1 1 calc R U . . .
C14 C 0.1878(3) 1.1378(3) 0.1733(2) 0.0381(7) Uani 1 1 d . . . . .
C15 C 0.2635(3) 1.2583(3) 0.2463(2) 0.0416(7) Uani 1 1 d . . . . .
H15A H 0.1955 1.2852 0.2822 0.050 Uiso 1 1 calc R U . . .
H15B H 0.3089 1.3234 0.2151 0.050 Uiso 1 1 calc R U . . .
C16 C 0.3736(3) 1.2492(2) 0.3144(2) 0.0360(6) Uani 1 1 d . . . . .
C17 C 0.4738(3) 1.2001(3) 0.2572(2) 0.0388(7) Uani 1 1 d . . . . .
H17A H 0.5319 1.2671 0.2317 0.047 Uiso 1 1 calc R U . . .
H17B H 0.5355 1.1814 0.2991 0.047 Uiso 1 1 calc R U . . .
O1 O 0.7266(2) 0.59020(18) -0.05281(16) 0.0510(6) Uani 1 1 d . . . . .
C18 C 0.8738(3) 0.6329(3) -0.0310(3) 0.0568(9) Uani 1 1 d . . . . .
H18A H 0.9155 0.7095 -0.0501 0.085 Uiso 1 1 calc R U . . .
H18B H 0.9082 0.5683 -0.0641 0.085 Uiso 1 1 calc R U . . .
H18C H 0.8982 0.6499 0.0360 0.085 Uiso 1 1 calc R U . . .
O2 O 0.0655(2) 1.1086(2) 0.14271(16) 0.0539(6) Uani 1 1 d . . . . .
C19 C 0.4538(3) 1.3797(3) 0.3802(2) 0.0485(8) Uani 1 1 d . . . . .
H19A H 0.4946 1.4379 0.3435 0.073 Uiso 1 1 calc R U . . .
H19B H 0.5272 1.3744 0.4206 0.073 Uiso 1 1 calc R U . . .
H19C H 0.3906 1.4096 0.4181 0.073 Uiso 1 1 calc R U . . .
C20 C 0.3040(3) 1.1589(3) 0.3727(2) 0.0469(8) Uani 1 1 d . . . . .
H20A H 0.3748 1.1543 0.4156 0.070 Uiso 1 1 calc R U . . .
H20B H 0.2542 1.0756 0.3312 0.070 Uiso 1 1 calc R U . . .
H20C H 0.2392 1.1899 0.4080 0.070 Uiso 1 1 calc R U . . .
C21 C 0.9613(3) 0.8177(3) 0.3958(2) 0.0427(7) Uani 1 1 d . . . . .
C22 C 1.0498(3) 0.8549(3) 0.4776(2) 0.0512(9) Uani 1 1 d . . . . .
H22 H 1.1212 0.9345 0.4938 0.061 Uiso 1 1 calc R U . . .
C23 C 1.0358(3) 0.7772(3) 0.5369(2) 0.0441(8) Uani 1 1 d . . . . .
C24 C 0.9294(3) 0.6602(2) 0.51384(19) 0.0317(6) Uani 1 1 d . . . . .
C25 C 0.8391(3) 0.6256(3) 0.4324(2) 0.0404(7) Uani 1 1 d . . . . .
H25 H 0.7653 0.5476 0.4172 0.048 Uiso 1 1 calc R U . . .
C26 C 0.8538(3) 0.7022(3) 0.3726(2) 0.0432(7) Uani 1 1 d . . . . .
H26 H 0.7916 0.6763 0.3172 0.052 Uiso 1 1 calc R U . . .
C27 C 1.1237(4) 0.8238(3) 0.6293(3) 0.0835(15) Uani 1 1 d D . . . .
H27A H 1.0788 0.8683 0.6756 0.100 Uiso 1 1 calc R U . . .
H27B H 1.2142 0.8844 0.6247 0.100 Uiso 1 1 calc R U . . .
C28 C 1.1468(3) 0.7179(3) 0.6630(3) 0.0728(13) Uani 1 1 d D . . . .
H28A H 1.2135 0.6889 0.6270 0.087 Uiso 1 1 calc R U . . .
H28B H 1.1874 0.7504 0.7292 0.087 Uiso 1 1 calc R U . . .
C29 C 1.0159(3) 0.6098(3) 0.6528(2) 0.0407(7) Uani 1 1 d . . . . .
C30 C 0.9138(3) 0.5781(2) 0.57714(19) 0.0307(6) Uani 1 1 d . . . . .
N2 N 0.7978(2) 0.4741(2) 0.55888(16) 0.0323(5) Uani 1 1 d . . . . .
C31 C 0.7801(3) 0.3997(2) 0.6167(2) 0.0337(6) Uani 1 1 d . . . . .
C32 C 0.8753(3) 0.4247(2) 0.6945(2) 0.0347(6) Uani 1 1 d . . . . .
C33 C 0.9947(3) 0.5326(3) 0.7114(2) 0.0412(7) Uani 1 1 d . . . . .
H33 H 1.0613 0.5524 0.7636 0.049 Uiso 1 1 calc R U . . .
C34 C 0.8536(3) 0.3403(3) 0.7566(2) 0.0412(7) Uani 1 1 d . . . . .
C35 C 0.7279(3) 0.2218(3) 0.7282(2) 0.0485(8) Uani 1 1 d . . . . .
H35A H 0.7004 0.1945 0.7843 0.058 Uiso 1 1 calc R U . . .
H35B H 0.7531 0.1554 0.6865 0.058 Uiso 1 1 calc R U . . .
C36 C 0.6024(3) 0.2361(3) 0.6781(2) 0.0429(8) Uani 1 1 d . . . . .
C37 C 0.6500(3) 0.2844(3) 0.5936(2) 0.0457(8) Uani 1 1 d . . . . .
H37A H 0.6664 0.2169 0.5468 0.055 Uiso 1 1 calc R U . . .
H37B H 0.5747 0.3039 0.5653 0.055 Uiso 1 1 calc R U . . .
O3 O 0.9881(2) 0.9010(2) 0.34191(17) 0.0593(7) Uani 1 1 d . . . . .
C38 C 0.9041(4) 0.8632(3) 0.2541(3) 0.0611(10) Uani 1 1 d . . . . .
H38A H 0.9088 0.7841 0.2171 0.092 Uiso 1 1 calc R U . . .
H38B H 0.9377 0.9274 0.2210 0.092 Uiso 1 1 calc R U . . .
H38C H 0.8083 0.8523 0.2642 0.092 Uiso 1 1 calc R U . . .
O4 O 0.9349(2) 0.3653(2) 0.82670(16) 0.0582(7) Uani 1 1 d . . . . .
C39 C 0.4860(4) 0.1080(3) 0.6446(3) 0.0667(11) Uani 1 1 d . . . . .
H39A H 0.4568 0.0766 0.6982 0.100 Uiso 1 1 calc R U . . .
H39B H 0.5196 0.0492 0.6027 0.100 Uiso 1 1 calc R U . . .
H39C H 0.4076 0.1165 0.6116 0.100 Uiso 1 1 calc R U . . .
C40 C 0.5510(4) 0.3285(3) 0.7453(3) 0.0592(10) Uani 1 1 d . . . . .
H40A H 0.6262 0.4092 0.7680 0.089 Uiso 1 1 calc R U . . .
H40B H 0.5202 0.2955 0.7979 0.089 Uiso 1 1 calc R U . . .
H40C H 0.4738 0.3395 0.7127 0.089 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
C1 O1 1.375(3) . ?
C1 C6 1.381(4) . ?
C1 C2 1.382(4) . ?
C2 C3 1.382(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.402(4) . ?
C3 C7 1.509(4) . ?
C4 C5 1.392(4) . ?
C4 C10 1.473(4) . ?
C5 C6 1.381(4) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.521(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C9 1.499(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C13 1.374(4) . ?
C9 C10 1.402(4) . ?
C10 N1 1.345(3) . ?
N1 C11 1.342(3) . ?
C11 C12 1.394(4) . ?
C11 C17 1.504(4) . ?
C12 C13 1.392(4) . ?
C12 C14 1.477(4) . ?
C13 H13 0.9400 . ?
C14 O2 1.222(3) . ?
C14 C15 1.491(4) . ?
C15 C16 1.530(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 C17 1.524(4) . ?
C16 C19 1.528(4) . ?
C16 C20 1.535(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
O1 C18 1.420(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 O3 1.369(3) . ?
C21 C22 1.370(4) . ?
C21 C26 1.383(4) . ?
C22 C23 1.387(4) . ?
C22 H22 0.9400 . ?
C23 C24 1.389(4) . ?
C23 C27 1.484(4) . ?
C24 C25 1.380(4) . ?
C24 C30 1.472(3) . ?
C25 C26 1.382(4) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
C27 C28 1.5217(19) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C28 C29 1.478(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C29 C33 1.370(4) . ?
C29 C30 1.393(4) . ?
C30 N2 1.350(3) . ?
N2 C31 1.337(3) . ?
C31 C32 1.389(4) . ?
C31 C37 1.504(4) . ?
C32 C33 1.397(4) . ?
C32 C34 1.476(4) . ?
C33 H33 0.9400 . ?
C34 O4 1.217(3) . ?
C34 C35 1.499(4) . ?
C35 C36 1.535(4) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C36 C39 1.523(4) . ?
C36 C40 1.525(5) . ?
C36 C37 1.528(4) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
O3 C38 1.418(4) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C38 H38C 0.9700 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 H39C 0.9700 . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 H40C 0.9700 . ?

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
O1 C1 C6 124.6(3) . . ?
O1 C1 C2 115.1(3) . . ?
C6 C1 C2 120.3(3) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 C7 121.3(3) . . ?
C4 C3 C7 118.6(3) . . ?
C5 C4 C3 118.1(3) . . ?
C5 C4 C10 122.0(2) . . ?
C3 C4 C10 119.9(2) . . ?
C6 C5 C4 121.8(3) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C3 C7 C8 110.0(2) . . ?
C3 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
C3 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C7 110.6(2) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C13 C9 C10 117.8(3) . . ?
C13 C9 C8 124.2(3) . . ?
C10 C9 C8 118.0(3) . . ?
N1 C10 C9 122.8(3) . . ?
N1 C10 C4 117.8(2) . . ?
C9 C10 C4 119.4(2) . . ?
C11 N1 C10 118.3(2) . . ?
N1 C11 C12 122.7(3) . . ?
N1 C11 C17 116.6(2) . . ?
C12 C11 C17 120.7(2) . . ?
C13 C12 C11 117.8(3) . . ?
C13 C12 C14 121.3(2) . . ?
C11 C12 C14 120.8(3) . . ?
C9 C13 C12 120.5(3) . . ?
C9 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
O2 C14 C12 120.9(3) . . ?
O2 C14 C15 121.8(3) . . ?
C12 C14 C15 117.2(2) . . ?
C14 C15 C16 114.0(2) . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C17 C16 C19 109.5(2) . . ?
C17 C16 C15 108.2(2) . . ?
C19 C16 C15 109.7(2) . . ?
C17 C16 C20 109.9(2) . . ?
C19 C16 C20 109.2(3) . . ?
C15 C16 C20 110.3(2) . . ?
C11 C17 C16 114.5(2) . . ?
C11 C17 H17A 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C11 C17 H17B 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C1 O1 C18 117.5(2) . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 C22 115.7(3) . . ?
O3 C21 C26 124.5(3) . . ?
C22 C21 C26 119.8(3) . . ?
C21 C22 C23 121.1(3) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C22 C23 C24 119.7(3) . . ?
C22 C23 C27 120.3(3) . . ?
C24 C23 C27 119.7(3) . . ?
C25 C24 C23 118.4(2) . . ?
C25 C24 C30 121.9(2) . . ?
C23 C24 C30 119.7(2) . . ?
C24 C25 C26 122.0(3) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 H25 119.0 . . ?
C25 C26 C21 118.9(3) . . ?
C25 C26 H26 120.5 . . ?
C21 C26 H26 120.5 . . ?
C23 C27 C28 112.5(3) . . ?
C23 C27 H27A 109.1 . . ?
C28 C27 H27A 109.1 . . ?
C23 C27 H27B 109.1 . . ?
C28 C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?
C29 C28 C27 112.2(3) . . ?
C29 C28 H28A 109.2 . . ?
C27 C28 H28A 109.2 . . ?
C29 C28 H28B 109.2 . . ?
C27 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C33 C29 C30 117.8(2) . . ?
C33 C29 C28 122.3(3) . . ?
C30 C29 C28 119.7(3) . . ?
N2 C30 C29 122.7(2) . . ?
N2 C30 C24 117.4(2) . . ?
C29 C30 C24 120.0(2) . . ?
C31 N2 C30 118.4(2) . . ?
N2 C31 C32 123.0(2) . . ?
N2 C31 C37 116.7(2) . . ?
C32 C31 C37 120.3(2) . . ?
C31 C32 C33 117.4(2) . . ?
C31 C32 C34 121.8(2) . . ?
C33 C32 C34 120.7(3) . . ?
C29 C33 C32 120.7(3) . . ?
C29 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
O4 C34 C32 121.4(3) . . ?
O4 C34 C35 122.0(3) . . ?
C32 C34 C35 116.6(3) . . ?
C34 C35 C36 114.0(2) . . ?
C34 C35 H35A 108.8 . . ?
C36 C35 H35A 108.8 . . ?
C34 C35 H35B 108.8 . . ?
C36 C35 H35B 108.8 . . ?
H35A C35 H35B 107.7 . . ?
C39 C36 C40 109.7(3) . . ?
C39 C36 C37 109.4(3) . . ?
C40 C36 C37 110.8(2) . . ?
C39 C36 C35 109.4(2) . . ?
C40 C36 C35 109.8(3) . . ?
C37 C36 C35 107.6(3) . . ?
C31 C37 C36 114.1(2) . . ?
C31 C37 H37A 108.7 . . ?
C36 C37 H37A 108.7 . . ?
C31 C37 H37B 108.7 . . ?
C36 C37 H37B 108.7 . . ?
H37A C37 H37B 107.6 . . ?
C21 O3 C38 117.5(2) . . ?
O3 C38 H38A 109.5 . . ?
O3 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O3 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C36 C40 H40A 109.5 . . ?
C36 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C36 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 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
O1 C1 C2 C3 -178.7(3) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C2 C3 C7 -179.3(3) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C7 C3 C4 C5 178.5(3) . . . . ?
C2 C3 C4 C10 179.5(3) . . . . ?
C7 C3 C4 C10 -1.8(4) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C10 C4 C5 C6 -178.8(2) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
O1 C1 C6 C5 179.3(3) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C2 C3 C7 C8 -144.7(3) . . . . ?
C4 C3 C7 C8 36.6(4) . . . . ?
C3 C7 C8 C9 -55.2(4) . . . . ?
C7 C8 C9 C13 -142.1(3) . . . . ?
C7 C8 C9 C10 41.9(4) . . . . ?
C13 C9 C10 N1 -2.3(4) . . . . ?
C8 C9 C10 N1 174.0(2) . . . . ?
C13 C9 C10 C4 176.9(2) . . . . ?
C8 C9 C10 C4 -6.8(4) . . . . ?
C5 C4 C10 N1 -15.7(4) . . . . ?
C3 C4 C10 N1 164.6(2) . . . . ?
C5 C4 C10 C9 165.0(2) . . . . ?
C3 C4 C10 C9 -14.7(4) . . . . ?
C9 C10 N1 C11 0.5(4) . . . . ?
C4 C10 N1 C11 -178.7(2) . . . . ?
C10 N1 C11 C12 2.5(4) . . . . ?
C10 N1 C11 C17 -177.2(2) . . . . ?
N1 C11 C12 C13 -3.7(4) . . . . ?
C17 C11 C12 C13 176.0(2) . . . . ?
N1 C11 C12 C14 178.7(2) . . . . ?
C17 C11 C12 C14 -1.6(4) . . . . ?
C10 C9 C13 C12 1.0(4) . . . . ?
C8 C9 C13 C12 -175.0(3) . . . . ?
C11 C12 C13 C9 1.8(4) . . . . ?
C14 C12 C13 C9 179.4(2) . . . . ?
C13 C12 C14 O2 7.9(4) . . . . ?
C11 C12 C14 O2 -174.6(3) . . . . ?
C13 C12 C14 C15 -170.5(3) . . . . ?
C11 C12 C14 C15 7.0(4) . . . . ?
O2 C14 C15 C16 146.5(3) . . . . ?
C12 C14 C15 C16 -35.1(4) . . . . ?
C14 C15 C16 C17 55.4(3) . . . . ?
C14 C15 C16 C19 174.8(3) . . . . ?
C14 C15 C16 C20 -64.9(3) . . . . ?
N1 C11 C17 C16 -155.8(2) . . . . ?
C12 C11 C17 C16 24.5(4) . . . . ?
C19 C16 C17 C11 -169.1(2) . . . . ?
C15 C16 C17 C11 -49.6(3) . . . . ?
C20 C16 C17 C11 70.9(3) . . . . ?
C6 C1 O1 C18 -4.0(4) . . . . ?
C2 C1 O1 C18 175.4(3) . . . . ?
O3 C21 C22 C23 -178.2(3) . . . . ?
C26 C21 C22 C23 1.7(5) . . . . ?
C21 C22 C23 C24 -0.8(5) . . . . ?
C21 C22 C23 C27 -174.1(4) . . . . ?
C22 C23 C24 C25 -0.8(5) . . . . ?
C27 C23 C24 C25 172.4(3) . . . . ?
C22 C23 C24 C30 -179.5(3) . . . . ?
C27 C23 C24 C30 -6.2(5) . . . . ?
C23 C24 C25 C26 1.7(5) . . . . ?
C30 C24 C25 C26 -179.7(3) . . . . ?
C24 C25 C26 C21 -0.8(5) . . . . ?
O3 C21 C26 C25 179.0(3) . . . . ?
C22 C21 C26 C25 -0.9(5) . . . . ?
C22 C23 C27 C28 -152.8(4) . . . . ?
C24 C23 C27 C28 34.0(5) . . . . ?
C23 C27 C28 C29 -46.7(5) . . . . ?
C27 C28 C29 C33 -150.6(4) . . . . ?
C27 C28 C29 C30 34.5(5) . . . . ?
C33 C29 C30 N2 -1.3(4) . . . . ?
C28 C29 C30 N2 173.8(3) . . . . ?
C33 C29 C30 C24 178.0(3) . . . . ?
C28 C29 C30 C24 -6.8(4) . . . . ?
C25 C24 C30 N2 -7.9(4) . . . . ?
C23 C24 C30 N2 170.7(3) . . . . ?
C25 C24 C30 C29 172.7(3) . . . . ?
C23 C24 C30 C29 -8.7(4) . . . . ?
C29 C30 N2 C31 0.8(4) . . . . ?
C24 C30 N2 C31 -178.5(2) . . . . ?
C30 N2 C31 C32 0.1(4) . . . . ?
C30 N2 C31 C37 -179.6(3) . . . . ?
N2 C31 C32 C33 -0.4(4) . . . . ?
C37 C31 C32 C33 179.3(3) . . . . ?
N2 C31 C32 C34 -179.4(3) . . . . ?
C37 C31 C32 C34 0.3(4) . . . . ?
C30 C29 C33 C32 1.0(5) . . . . ?
C28 C29 C33 C32 -174.0(3) . . . . ?
C31 C32 C33 C29 -0.2(4) . . . . ?
C34 C32 C33 C29 178.9(3) . . . . ?
C31 C32 C34 O4 -177.2(3) . . . . ?
C33 C32 C34 O4 3.8(5) . . . . ?
C31 C32 C34 C35 3.7(4) . . . . ?
C33 C32 C34 C35 -175.3(3) . . . . ?
O4 C34 C35 C36 147.7(3) . . . . ?
C32 C34 C35 C36 -33.1(4) . . . . ?
C34 C35 C36 C39 174.8(3) . . . . ?
C34 C35 C36 C40 -64.7(3) . . . . ?
C34 C35 C36 C37 56.0(4) . . . . ?
N2 C31 C37 C36 -154.9(3) . . . . ?
C32 C31 C37 C36 25.4(4) . . . . ?
C39 C36 C37 C31 -170.4(3) . . . . ?
C40 C36 C37 C31 68.5(3) . . . . ?
C35 C36 C37 C31 -51.6(3) . . . . ?
C22 C21 O3 C38 176.5(3) . . . . ?
C26 C21 O3 C38 -3.4(5) . . . . ?

_refine_diff_density_max         0.658
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.064



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/EtOAc'
####################################################################### 
# 
# 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_Lee-C
_database_code_depnum_ccdc_archive 'CCDC 2077449'
loop_
_audit_author_name
_audit_author_address
'Ha Jin Lee'
;Yeungnam University
South Korea
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
8,8-Dimethyl-6,7,8,11-tetrahydro-9H-indeno[1,2-b]quinolin-9-one
_chemical_name_common            ?
_chemical_melting_point          413
_chemical_formula_moiety         'C18 H17 N O'
_chemical_formula_sum            'C18 H17 N O'
_chemical_formula_weight         263.32

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.8897(12)
_cell_length_b                   19.960(4)
_cell_length_c                   11.987(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.094(7)
_cell_angle_gamma                90
_cell_volume                     1372.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4760
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      26.76

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6175
_exptl_absorpt_correction_T_max  0.6934
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PHOTON III M14'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22261
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_av_R_equivalents  0.1023
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.685
_diffrn_reflns_theta_max         28.576
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3456
_reflns_number_gt                2355
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0596P)²+0.3669P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3456
_refine_ls_number_parameters     213
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1594
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.047
_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 0.5653(2) 0.38555(6) 0.16044(11) 0.0470(4) Uani 1 1 d . . . . .
C1 C 0.4464(3) 0.35500(8) 0.21407(15) 0.0344(4) Uani 1 1 d . . . . .
C2 C 0.2867(3) 0.29815(8) 0.16208(14) 0.0413(4) Uani 1 1 d D . . . .
C3A C 0.0718(4) 0.29790(14) 0.2121(2) 0.0436(6) Uani 0.798(4) 1 d . . P A 1
H3A H -0.0188 0.3385 0.1869 0.052 Uiso 0.798(4) 1 calc R U P A 1
H3B H -0.0253 0.2594 0.1811 0.052 Uiso 0.798(4) 1 calc R U P A 1
C3B C 0.190(2) 0.2598(6) 0.2434(9) 0.053(3) Uani 0.202(4) 1 d . . P A 2
H3B1 H 0.3034 0.2250 0.2755 0.063 Uiso 0.202(4) 1 calc R U P A 2
H3B2 H 0.0505 0.2368 0.2000 0.063 Uiso 0.202(4) 1 calc R U P A 2
C4 C 0.1237(3) 0.29470(10) 0.34112(17) 0.0464(5) Uani 1 1 d . . . . .
H4A H -0.0195 0.3045 0.3667 0.056 Uiso 1 1 calc R U . A 1
H4B H 0.1721 0.2490 0.3656 0.056 Uiso 1 1 calc R U . A 1
C5 C 0.3107(3) 0.34276(8) 0.39845(15) 0.0349(4) Uani 1 1 d . . . . .
C6 C 0.4645(3) 0.37038(8) 0.33749(14) 0.0319(4) Uani 1 1 d . . . . .
C7 C 0.6430(3) 0.41284(8) 0.39401(14) 0.0340(4) Uani 1 1 d . . . . .
H7 H 0.7473 0.4323 0.3546 0.041 Uiso 1 1 calc R U . . .
C8 C 0.6618(3) 0.42527(8) 0.50818(14) 0.0325(4) Uani 1 1 d . . . . .
C9 C 0.4966(3) 0.39626(8) 0.56137(14) 0.0326(4) Uani 1 1 d . . . . .
N1 N 0.3227(2) 0.35626(7) 0.50989(12) 0.0373(4) Uani 1 1 d . . . . .
C10 C 0.5498(3) 0.41622(8) 0.68195(14) 0.0359(4) Uani 1 1 d . . . . .
C11 C 0.7502(3) 0.45602(8) 0.70207(15) 0.0373(4) Uani 1 1 d . . . . .
C12 C 0.8366(3) 0.46480(9) 0.59436(14) 0.0383(4) Uani 1 1 d . . . . .
H12A H 0.9942 0.4466 0.6030 0.046 Uiso 1 1 calc R U . . .
H12B H 0.8365 0.5121 0.5725 0.046 Uiso 1 1 calc R U . . .
C13 C 0.8426(4) 0.48087(10) 0.81087(16) 0.0492(5) Uani 1 1 d . . . . .
H13 H 0.9783 0.5072 0.8255 0.059 Uiso 1 1 calc R U . . .
C14 C 0.7302(4) 0.46594(11) 0.89748(18) 0.0583(6) Uani 1 1 d . . . . .
H14 H 0.7900 0.4829 0.9715 0.070 Uiso 1 1 calc R U . . .
C15 C 0.5319(4) 0.42665(11) 0.87750(17) 0.0552(5) Uani 1 1 d . . . . .
H15 H 0.4598 0.4170 0.9380 0.066 Uiso 1 1 calc R U . . .
C16 C 0.4385(4) 0.40135(9) 0.76956(16) 0.0463(5) Uani 1 1 d . . . . .
H16 H 0.3032 0.3748 0.7557 0.056 Uiso 1 1 calc R U . . .
C17A C 0.4322(4) 0.23356(9) 0.1946(2) 0.0496(7) Uani 0.798(4) 1 d D . P A 1
H17A H 0.3343 0.1947 0.1707 0.074 Uiso 0.798(4) 1 calc R U P A 1
H17B H 0.4923 0.2322 0.2769 0.074 Uiso 0.798(4) 1 calc R U P A 1
H17C H 0.5612 0.2333 0.1566 0.074 Uiso 0.798(4) 1 calc R U P A 1
C18A C 0.2193(5) 0.30342(15) 0.03130(16) 0.0592(8) Uani 0.798(4) 1 d D . P A 1
H18A H 0.1314 0.3443 0.0094 0.089 Uiso 0.798(4) 1 calc R U P A 1
H18B H 0.1246 0.2651 0.0001 0.089 Uiso 0.798(4) 1 calc R U P A 1
H18C H 0.3593 0.3042 0.0015 0.089 Uiso 0.798(4) 1 calc R U P A 1
C17B C 0.385(2) 0.2592(6) 0.0729(9) 0.071(4) Uani 0.202(4) 1 d D . P A 2
H17D H 0.5204 0.2335 0.1115 0.106 Uiso 0.202(4) 1 calc R U P A 2
H17E H 0.4311 0.2905 0.0200 0.106 Uiso 0.202(4) 1 calc R U P A 2
H17F H 0.2673 0.2290 0.0310 0.106 Uiso 0.202(4) 1 calc R U P A 2
C18B C 0.0812(16) 0.3369(6) 0.0870(11) 0.088(5) Uani 0.202(4) 1 d D . P A 2
H18D H -0.0261 0.3056 0.0406 0.132 Uiso 0.202(4) 1 calc R U P A 2
H18E H 0.1398 0.3677 0.0374 0.132 Uiso 0.202(4) 1 calc R U P A 2
H18F H 0.0006 0.3620 0.1357 0.132 Uiso 0.202(4) 1 calc R U P A 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.216(2) . ?
C1 C6 1.491(2) . ?
C1 C2 1.515(2) . ?
C2 C3B 1.454(11) . ?
C2 C3A 1.518(3) . ?
C2 C18A 1.5311(18) . ?
C2 C17B 1.538(2) . ?
C2 C18B 1.543(2) . ?
C2 C17A 1.5482(17) . ?
C3A C4 1.509(3) . ?
C3A H3A 0.9800 . ?
C3A H3B 0.9800 . ?
C3B C4 1.489(10) . ?
C3B H3B1 0.9800 . ?
C3B H3B2 0.9800 . ?
C4 C5 1.504(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 N1 1.349(2) . ?
C5 C6 1.400(2) . ?
C6 C7 1.400(2) . ?
C7 C8 1.370(2) . ?
C7 H7 0.9400 . ?
C8 C9 1.403(2) . ?
C8 C12 1.506(2) . ?
C9 N1 1.335(2) . ?
C9 C10 1.463(2) . ?
C10 C16 1.390(2) . ?
C10 C11 1.398(2) . ?
C11 C13 1.386(3) . ?
C11 C12 1.501(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.382(3) . ?
C14 H14 0.9400 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C17A H17C 0.9700 . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C18A H18C 0.9700 . ?
C17B H17D 0.9700 . ?
C17B H17E 0.9700 . ?
C17B H17F 0.9700 . ?
C18B H18D 0.9700 . ?
C18B H18E 0.9700 . ?
C18B H18F 0.9700 . ?

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
O1 C1 C6 120.05(15) . . ?
O1 C1 C2 122.42(15) . . ?
C6 C1 C2 117.43(14) . . ?
C3B C2 C1 114.8(4) . . ?
C1 C2 C3A 109.59(15) . . ?
C1 C2 C18A 111.26(16) . . ?
C3A C2 C18A 111.01(18) . . ?
C3B C2 C17B 117.9(7) . . ?
C1 C2 C17B 111.5(5) . . ?
C3B C2 C18B 106.3(7) . . ?
C1 C2 C18B 101.3(5) . . ?
C17B C2 C18B 102.6(8) . . ?
C1 C2 C17A 105.28(15) . . ?
C3A C2 C17A 111.16(18) . . ?
C18A C2 C17A 108.39(19) . . ?
C4 C3A C2 114.32(18) . . ?
C4 C3A H3A 108.7 . . ?
C2 C3A H3A 108.7 . . ?
C4 C3A H3B 108.7 . . ?
C2 C3A H3B 108.7 . . ?
H3A C3A H3B 107.6 . . ?
C2 C3B C4 119.6(7) . . ?
C2 C3B H3B1 107.4 . . ?
C4 C3B H3B1 107.4 . . ?
C2 C3B H3B2 107.4 . . ?
C4 C3B H3B2 107.4 . . ?
H3B1 C3B H3B2 107.0 . . ?
C3B C4 C5 111.3(4) . . ?
C5 C4 C3A 113.50(16) . . ?
C5 C4 H4A 108.9 . . ?
C3A C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3A C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
N1 C5 C6 122.92(15) . . ?
N1 C5 C4 116.66(15) . . ?
C6 C5 C4 120.41(15) . . ?
C7 C6 C5 119.32(15) . . ?
C7 C6 C1 118.82(14) . . ?
C5 C6 C1 121.85(15) . . ?
C8 C7 C6 118.36(15) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
C7 C8 C9 118.12(15) . . ?
C7 C8 C12 131.93(15) . . ?
C9 C8 C12 109.93(15) . . ?
N1 C9 C8 125.12(15) . . ?
N1 C9 C10 126.13(15) . . ?
C8 C9 C10 108.74(14) . . ?
C9 N1 C5 116.11(14) . . ?
C16 C10 C11 121.03(17) . . ?
C16 C10 C9 131.00(17) . . ?
C11 C10 C9 107.96(15) . . ?
C13 C11 C10 120.10(17) . . ?
C13 C11 C12 129.08(17) . . ?
C10 C11 C12 110.82(15) . . ?
C11 C12 C8 102.53(14) . . ?
C11 C12 H12A 111.3 . . ?
C8 C12 H12A 111.3 . . ?
C11 C12 H12B 111.3 . . ?
C8 C12 H12B 111.3 . . ?
H12A C12 H12B 109.2 . . ?
C14 C13 C11 118.5(2) . . ?
C14 C13 H13 120.8 . . ?
C11 C13 H13 120.8 . . ?
C15 C14 C13 121.40(19) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 120.8(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C10 118.24(19) . . ?
C15 C16 H16 120.9 . . ?
C10 C16 H16 120.9 . . ?
C2 C17A H17A 109.5 . . ?
C2 C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C2 C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C2 C18A H18A 109.5 . . ?
C2 C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C2 C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C2 C17B H17D 109.5 . . ?
C2 C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C2 C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C2 C18B H18D 109.5 . . ?
C2 C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C2 C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 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
O1 C1 C2 C3B 169.6(6) . . . . ?
C6 C1 C2 C3B -6.9(6) . . . . ?
O1 C1 C2 C3A -146.32(19) . . . . ?
C6 C1 C2 C3A 37.1(2) . . . . ?
O1 C1 C2 C18A -23.2(3) . . . . ?
C6 C1 C2 C18A 160.25(18) . . . . ?
O1 C1 C2 C17B 32.2(6) . . . . ?
C6 C1 C2 C17B -144.4(6) . . . . ?
O1 C1 C2 C18B -76.3(6) . . . . ?
C6 C1 C2 C18B 107.1(6) . . . . ?
O1 C1 C2 C17A 94.0(2) . . . . ?
C6 C1 C2 C17A -82.54(19) . . . . ?
C1 C2 C3A C4 -55.1(2) . . . . ?
C18A C2 C3A C4 -178.42(19) . . . . ?
C17A C2 C3A C4 60.8(2) . . . . ?
C1 C2 C3B C4 36.7(11) . . . . ?
C17B C2 C3B C4 171.3(8) . . . . ?
C18B C2 C3B C4 -74.4(10) . . . . ?
C2 C3B C4 C5 -45.6(10) . . . . ?
C2 C3A C4 C5 46.5(3) . . . . ?
C3B C4 C5 N1 -153.6(6) . . . . ?
C3A C4 C5 N1 162.38(17) . . . . ?
C3B C4 C5 C6 25.4(6) . . . . ?
C3A C4 C5 C6 -18.7(3) . . . . ?
N1 C5 C6 C7 1.4(2) . . . . ?
C4 C5 C6 C7 -177.41(16) . . . . ?
N1 C5 C6 C1 -179.57(15) . . . . ?
C4 C5 C6 C1 1.6(2) . . . . ?
O1 C1 C6 C7 -9.3(2) . . . . ?
C2 C1 C6 C7 167.32(14) . . . . ?
O1 C1 C6 C5 171.65(15) . . . . ?
C2 C1 C6 C5 -11.7(2) . . . . ?
C5 C6 C7 C8 0.7(2) . . . . ?
C1 C6 C7 C8 -178.33(14) . . . . ?
C6 C7 C8 C9 -1.9(2) . . . . ?
C6 C7 C8 C12 176.53(16) . . . . ?
C7 C8 C9 N1 1.1(2) . . . . ?
C12 C8 C9 N1 -177.62(15) . . . . ?
C7 C8 C9 C10 -179.88(14) . . . . ?
C12 C8 C9 C10 1.40(18) . . . . ?
C8 C9 N1 C5 0.9(2) . . . . ?
C10 C9 N1 C5 -177.91(15) . . . . ?
C6 C5 N1 C9 -2.2(2) . . . . ?
C4 C5 N1 C9 176.70(15) . . . . ?
N1 C9 C10 C16 -1.6(3) . . . . ?
C8 C9 C10 C16 179.40(17) . . . . ?
N1 C9 C10 C11 177.66(15) . . . . ?
C8 C9 C10 C11 -1.34(18) . . . . ?
C16 C10 C11 C13 0.6(3) . . . . ?
C9 C10 C11 C13 -178.75(16) . . . . ?
C16 C10 C11 C12 -179.89(16) . . . . ?
C9 C10 C11 C12 0.76(19) . . . . ?
C13 C11 C12 C8 179.52(18) . . . . ?
C10 C11 C12 C8 0.06(18) . . . . ?
C7 C8 C12 C11 -179.38(17) . . . . ?
C9 C8 C12 C11 -0.90(18) . . . . ?
C10 C11 C13 C14 -0.7(3) . . . . ?
C12 C11 C13 C14 179.84(18) . . . . ?
C11 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C10 0.3(3) . . . . ?
C11 C10 C16 C15 -0.4(3) . . . . ?
C9 C10 C16 C15 178.81(17) . . . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.043



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/EtOAc'
####################################################################### 
# 
# 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_Lee-B
_database_code_depnum_ccdc_archive 'CCDC 2077450'
loop_
_audit_author_name
_audit_author_address
'Ha Jin Lee'
;Yeungnam University
South Korea
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
5,6,7,9,10,11-Hexahydrobenzo[6,7]cyclohepta[1,2-b]benzo[6,7]cyclohepta[2,1-e]pyridine
_chemical_name_common            ?
_chemical_melting_point          513
_chemical_formula_moiety         'C23 H21 N'
_chemical_formula_sum            'C23 H21 N'
_chemical_formula_weight         311.41

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.1052(10)
_cell_length_b                   16.1802(15)
_cell_length_c                   9.2208(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1656.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    5565
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      27.55

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6458
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PHOTON III M14'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21473
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.135
_diffrn_reflns_theta_max         28.339
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2066
_reflns_number_gt                1613
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0415P)²+0.5458P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2066
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
N1 N 0.5000 0.62107(8) 0.7500 0.0261(3) Uani 1 2 d S T P . .
C1 C 0.42082(10) 0.57881(7) 0.66827(12) 0.0253(3) Uani 1 1 d . . . . .
C2 C 0.33882(11) 0.62876(7) 0.57567(13) 0.0282(3) Uani 1 1 d . . . . .
C3 C 0.38472(12) 0.69501(7) 0.49682(14) 0.0350(3) Uani 1 1 d . . . . .
H3 H 0.4664 0.7092 0.5064 0.042 Uiso 1 1 calc R U . . .
C4 C 0.31182(14) 0.74031(8) 0.40438(16) 0.0441(4) Uani 1 1 d . . . . .
H4 H 0.3442 0.7844 0.3508 0.053 Uiso 1 1 calc R U . . .
C5 C 0.19153(14) 0.72048(9) 0.39123(17) 0.0469(4) Uani 1 1 d . . . . .
H5 H 0.1418 0.7506 0.3280 0.056 Uiso 1 1 calc R U . . .
C6 C 0.14459(12) 0.65598(9) 0.47163(16) 0.0422(3) Uani 1 1 d . . . . .
H6 H 0.0622 0.6434 0.4633 0.051 Uiso 1 1 calc R U . . .
C7 C 0.21597(11) 0.60917(8) 0.56454(14) 0.0329(3) Uani 1 1 d . . . . .
C8 C 0.16326(12) 0.54088(9) 0.65526(15) 0.0405(3) Uani 1 1 d . . . . .
H8A H 0.0753 0.5453 0.6525 0.049 Uiso 1 1 calc R U . . .
H8B H 0.1887 0.5488 0.7561 0.049 Uiso 1 1 calc R U . . .
C9 C 0.19913(12) 0.45397(9) 0.60717(16) 0.0396(3) Uani 1 1 d . . . . .
H9A H 0.1494 0.4378 0.5241 0.048 Uiso 1 1 calc R U . . .
H9B H 0.1826 0.4151 0.6863 0.048 Uiso 1 1 calc R U . . .
C10 C 0.33200(11) 0.44728(8) 0.56475(14) 0.0315(3) Uani 1 1 d . . . . .
H10A H 0.3544 0.3887 0.5624 0.038 Uiso 1 1 calc R U . . .
H10B H 0.3419 0.4692 0.4664 0.038 Uiso 1 1 calc R U . . .
C11 C 0.41748(10) 0.49205(7) 0.66417(12) 0.0260(3) Uani 1 1 d . . . . .
C12 C 0.5000 0.45026(10) 0.7500 0.0272(3) Uani 1 2 d S T P . .
H12 H 0.5000 0.3922 0.7500 0.033 Uiso 1 2 calc R U P . .


_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 1.3448(13) . ?
N1 C1 1.3448(13) 3_656 ?
C1 C11 1.4049(16) . ?
C1 C2 1.4871(16) . ?
C2 C3 1.3920(17) . ?
C2 C7 1.4044(17) . ?
C3 C4 1.3853(18) . ?
C3 H3 0.9400 . ?
C4 C5 1.379(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.3914(18) . ?
C6 H6 0.9400 . ?
C7 C8 1.5044(19) . ?
C8 C9 1.5273(19) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C10 1.5303(18) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C11 1.5053(16) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 C12 1.3868(14) . ?
C12 C11 1.3868(14) 3_656 ?
C12 H12 0.9400 . ?

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 N1 C1 118.88(14) . 3_656 ?
N1 C1 C11 122.72(11) . . ?
N1 C1 C2 116.48(10) . . ?
C11 C1 C2 120.75(10) . . ?
C3 C2 C7 119.43(11) . . ?
C3 C2 C1 119.62(11) . . ?
C7 C2 C1 120.95(11) . . ?
C4 C3 C2 120.99(13) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 119.81(14) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 119.59(13) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 121.77(13) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C2 118.40(12) . . ?
C6 C7 C8 121.37(12) . . ?
C2 C7 C8 120.20(11) . . ?
C7 C8 C9 114.41(11) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 C10 113.00(11) . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 114.73(11) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C1 117.02(11) . . ?
C12 C11 C10 121.98(11) . . ?
C1 C11 C10 120.92(11) . . ?
C11 C12 C11 121.65(15) 3_656 . ?
C11 C12 H12 119.2 3_656 . ?
C11 C12 H12 119.2 . . ?

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 N1 C1 C11 -0.22(8) 3_656 . . . ?
C1 N1 C1 C2 -177.60(11) 3_656 . . . ?
N1 C1 C2 C3 44.12(15) . . . . ?
C11 C1 C2 C3 -133.31(12) . . . . ?
N1 C1 C2 C7 -137.02(11) . . . . ?
C11 C1 C2 C7 45.55(16) . . . . ?
C7 C2 C3 C4 -1.92(19) . . . . ?
C1 C2 C3 C4 176.96(12) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C7 -1.0(2) . . . . ?
C5 C6 C7 C2 0.0(2) . . . . ?
C5 C6 C7 C8 177.97(13) . . . . ?
C3 C2 C7 C6 1.47(18) . . . . ?
C1 C2 C7 C6 -177.39(11) . . . . ?
C3 C2 C7 C8 -176.53(11) . . . . ?
C1 C2 C7 C8 4.61(18) . . . . ?
C6 C7 C8 C9 109.22(14) . . . . ?
C2 C7 C8 C9 -72.84(16) . . . . ?
C7 C8 C9 C10 41.60(16) . . . . ?
C8 C9 C10 C11 42.25(16) . . . . ?
N1 C1 C11 C12 0.43(15) . . . . ?
C2 C1 C11 C12 177.70(9) . . . . ?
N1 C1 C11 C10 -176.52(9) . . . . ?
C2 C1 C11 C10 0.76(17) . . . . ?
C9 C10 C11 C12 113.26(12) . . . . ?
C9 C10 C11 C1 -69.96(15) . . . . ?
C1 C11 C12 C11 -0.20(7) . . . 3_656 ?
C10 C11 C12 C11 176.71(12) . . . 3_656 ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.037



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/EtOAc'
