# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_20210324AR_0m
_database_code_depnum_ccdc_archive 'CCDC 2087413'
loop_
_audit_author_name
_audit_author_address
'Ryan VanderLinden'
;University of Utah
United States of America
;
_audit_update_record             
;
2021-06-01 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
6-methyl-6,7-dihydro-5H-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]pyrido[2,3-e]azepine
_chemical_name_common            deoxytoddaquinoline
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N2 O2'
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28

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                   7.6358(9)
_cell_length_b                   9.0784(11)
_cell_length_c                   9.7663(13)
_cell_angle_alpha                109.932(3)
_cell_angle_beta                 107.117(3)
_cell_angle_gamma                92.339(3)
_cell_volume                     600.71(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4733
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      36.79

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             268
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7034
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine focus 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            18138
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.676
_diffrn_reflns_theta_max         35.631
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5526
_reflns_number_gt                4242
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Bruker SHELXTL'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0659P)²+0.0913P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         5526
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1244
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_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 -0.04710(9) 0.12826(8) 0.33346(7) 0.01585(13) Uani 1 1 d . . . . .
O2 O 0.13498(9) 0.09074(8) 0.17628(7) 0.01650(13) Uani 1 1 d . . . . .
N3 N 0.41644(11) 0.19534(10) 0.87765(9) 0.01477(14) Uani 1 1 d . . . . .
N4 N 0.82584(10) 0.38650(9) 0.70667(8) 0.01218(13) Uani 1 1 d . . . . .
C5 C -0.04763(12) 0.04627(12) 0.17891(10) 0.01683(17) Uani 1 1 d . . . . .
H5A H -0.143382 0.077439 0.105086 0.020 Uiso 1 1 calc R U . . .
H5B H -0.074435 -0.069896 0.150376 0.020 Uiso 1 1 calc R U . . .
C6 C 0.13769(11) 0.15685(10) 0.42218(9) 0.01141(14) Uani 1 1 d . . . . .
C7 C 0.24730(12) 0.13575(10) 0.32767(9) 0.01156(14) Uani 1 1 d . . . . .
C8 C 0.43785(12) 0.15900(10) 0.38565(9) 0.01212(14) Uani 1 1 d . . . . .
H8 H 0.511299 0.143762 0.319989 0.015 Uiso 1 1 calc R U . . .
C9 C 0.51949(11) 0.20639(10) 0.54659(9) 0.01057(14) Uani 1 1 d . . . . .
C10 C 0.40841(11) 0.22832(10) 0.64191(9) 0.01074(14) Uani 1 1 d . . . . .
C11 C 0.21274(11) 0.20234(10) 0.57929(9) 0.01201(14) Uani 1 1 d . . . . .
H11 H 0.136811 0.215721 0.642856 0.014 Uiso 1 1 calc R U . . .
C12 C 0.49780(11) 0.27108(10) 0.80995(9) 0.01136(14) Uani 1 1 d . . . . .
C13 C 0.49737(13) 0.22930(12) 1.02886(10) 0.01674(16) Uani 1 1 d . . . . .
H13 H 0.440975 0.176494 1.077685 0.020 Uiso 1 1 calc R U . . .
C14 C 0.65903(13) 0.33728(12) 1.11844(10) 0.01700(17) Uani 1 1 d . . . . .
H14 H 0.712904 0.355763 1.224924 0.020 Uiso 1 1 calc R U . . .
C15 C 0.74012(12) 0.41772(11) 1.04840(10) 0.01532(16) Uani 1 1 d . . . . .
H15 H 0.849554 0.493532 1.107026 0.018 Uiso 1 1 calc R U . . .
C16 C 0.65914(11) 0.38589(10) 0.89140(9) 0.01209(14) Uani 1 1 d . . . . .
C17 C 0.73099(12) 0.47801(10) 0.81157(10) 0.01371(15) Uani 1 1 d . . . . .
H17A H 0.625675 0.515214 0.751991 0.016 Uiso 1 1 calc R U . . .
H17B H 0.818459 0.572874 0.890637 0.016 Uiso 1 1 calc R U . . .
C18 C 0.72757(11) 0.22280(10) 0.61712(10) 0.01225(14) Uani 1 1 d . . . . .
H18A H 0.753653 0.161427 0.685469 0.015 Uiso 1 1 calc R U . . .
H18B H 0.779338 0.174167 0.533273 0.015 Uiso 1 1 calc R U . . .
C19 C 0.84486(13) 0.46973(11) 0.60621(11) 0.01617(16) Uani 1 1 d . . . . .
H19A H 0.907904 0.409379 0.536116 0.024 Uiso 1 1 calc R U . . .
H19B H 0.721604 0.480297 0.546064 0.024 Uiso 1 1 calc R U . . .
H19C H 0.917830 0.575347 0.669087 0.024 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 C6 1.3807(10) . ?
O1 C5 1.4362(11) . ?
O2 C7 1.3790(10) . ?
O2 C5 1.4457(11) . ?
N3 C13 1.3397(11) . ?
N3 C12 1.3464(11) . ?
N4 C19 1.4612(11) . ?
N4 C17 1.4730(11) . ?
N4 C18 1.4741(11) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.3728(11) . ?
C6 C7 1.3915(11) . ?
C7 C8 1.3750(12) . ?
C8 C9 1.4087(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.4063(11) . ?
C9 C18 1.5125(12) . ?
C10 C11 1.4131(12) . ?
C10 C12 1.4813(11) . ?
C11 H11 0.9500 . ?
C12 C16 1.4106(12) . ?
C13 C14 1.3895(13) . ?
C13 H13 0.9500 . ?
C14 C15 1.3919(13) . ?
C14 H14 0.9500 . ?
C15 C16 1.3936(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.5057(12) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C5 104.08(6) . . ?
C7 O2 C5 104.09(6) . . ?
C13 N3 C12 117.47(8) . . ?
C19 N4 C17 109.09(7) . . ?
C19 N4 C18 111.60(7) . . ?
C17 N4 C18 111.59(6) . . ?
O1 C5 O2 106.67(7) . . ?
O1 C5 H5A 110.4 . . ?
O2 C5 H5A 110.4 . . ?
O1 C5 H5B 110.4 . . ?
O2 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
C11 C6 O1 128.28(7) . . ?
C11 C6 C7 122.19(8) . . ?
O1 C6 C7 109.52(7) . . ?
C8 C7 O2 128.42(7) . . ?
C8 C7 C6 122.15(7) . . ?
O2 C7 C6 109.43(7) . . ?
C7 C8 C9 117.14(7) . . ?
C7 C8 H8 121.4 . . ?
C9 C8 H8 121.4 . . ?
C10 C9 C8 120.59(7) . . ?
C10 C9 C18 119.33(7) . . ?
C8 C9 C18 119.94(7) . . ?
C9 C10 C11 121.15(7) . . ?
C9 C10 C12 119.38(7) . . ?
C11 C10 C12 119.39(7) . . ?
C6 C11 C10 116.78(7) . . ?
C6 C11 H11 121.6 . . ?
C10 C11 H11 121.6 . . ?
N3 C12 C16 123.12(7) . . ?
N3 C12 C10 116.42(7) . . ?
C16 C12 C10 120.46(7) . . ?
N3 C13 C14 123.80(8) . . ?
N3 C13 H13 118.1 . . ?
C14 C13 H13 118.1 . . ?
C13 C14 C15 118.41(8) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C14 C15 C16 119.32(8) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C12 117.84(8) . . ?
C15 C16 C17 121.88(7) . . ?
C12 C16 C17 120.14(7) . . ?
N4 C17 C16 113.89(7) . . ?
N4 C17 H17A 108.8 . . ?
C16 C17 H17A 108.8 . . ?
N4 C17 H17B 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
N4 C18 C9 115.53(7) . . ?
N4 C18 H18A 108.4 . . ?
C9 C18 H18A 108.4 . . ?
N4 C18 H18B 108.4 . . ?
C9 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
N4 C19 H19A 109.5 . . ?
N4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C6 O1 C5 O2 -24.36(9) . . . . ?
C7 O2 C5 O1 23.83(9) . . . . ?
C5 O1 C6 C11 -165.45(9) . . . . ?
C5 O1 C6 C7 15.77(10) . . . . ?
C5 O2 C7 C8 165.94(9) . . . . ?
C5 O2 C7 C6 -14.20(9) . . . . ?
C11 C6 C7 C8 0.05(13) . . . . ?
O1 C6 C7 C8 178.92(8) . . . . ?
C11 C6 C7 O2 -179.82(8) . . . . ?
O1 C6 C7 O2 -0.96(10) . . . . ?
O2 C7 C8 C9 179.55(8) . . . . ?
C6 C7 C8 C9 -0.30(13) . . . . ?
C7 C8 C9 C10 0.01(12) . . . . ?
C7 C8 C9 C18 175.67(8) . . . . ?
C8 C9 C10 C11 0.52(12) . . . . ?
C18 C9 C10 C11 -175.16(7) . . . . ?
C8 C9 C10 C12 177.24(7) . . . . ?
C18 C9 C10 C12 1.56(12) . . . . ?
O1 C6 C11 C10 -178.17(8) . . . . ?
C7 C6 C11 C10 0.47(13) . . . . ?
C9 C10 C11 C6 -0.75(12) . . . . ?
C12 C10 C11 C6 -177.46(8) . . . . ?
C13 N3 C12 C16 -1.77(13) . . . . ?
C13 N3 C12 C10 178.43(8) . . . . ?
C9 C10 C12 N3 -137.08(8) . . . . ?
C11 C10 C12 N3 39.70(11) . . . . ?
C9 C10 C12 C16 43.11(12) . . . . ?
C11 C10 C12 C16 -140.11(9) . . . . ?
C12 N3 C13 C14 -0.02(14) . . . . ?
N3 C13 C14 C15 1.42(15) . . . . ?
C13 C14 C15 C16 -1.04(14) . . . . ?
C14 C15 C16 C12 -0.59(13) . . . . ?
C14 C15 C16 C17 175.00(8) . . . . ?
N3 C12 C16 C15 2.09(13) . . . . ?
C10 C12 C16 C15 -178.12(8) . . . . ?
N3 C12 C16 C17 -173.59(8) . . . . ?
C10 C12 C16 C17 6.21(12) . . . . ?
C19 N4 C17 C16 164.92(7) . . . . ?
C18 N4 C17 C16 41.14(10) . . . . ?
C15 C16 C17 N4 108.92(9) . . . . ?
C12 C16 C17 N4 -75.59(10) . . . . ?
C19 N4 C18 C9 -76.55(9) . . . . ?
C17 N4 C18 C9 45.80(10) . . . . ?
C10 C9 C18 N4 -74.41(10) . . . . ?
C8 C9 C18 N4 109.87(9) . . . . ?

_refine_diff_density_max         0.616
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.062


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methylene chloride'
_chemical_properties_physical    'Not sensitive'
####################################################################### 
# 
# 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_cu_20122_0m
_database_code_depnum_ccdc_archive 'CCDC 2087414'
loop_
_audit_author_name
_audit_author_address
'Ryan VanderLinden'
;University of Utah
United States of America
;
_audit_update_record             
;
2021-06-01 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'Methyl 6-methyl-6,7-dihydro-5H-benzo[c]pyrido[2,3-e]azepine-10-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   9.9992(5)
_cell_length_b                   11.2900(5)
_cell_length_c                   12.2822(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.733(2)
_cell_angle_gamma                90
_cell_volume                     1334.60(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9878
_cell_measurement_theta_min      3.74
_cell_measurement_theta_max      72.12

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.720
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7023
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC Diamond micro-focus sealed tube'
_diffrn_measurement_device_type  'BRUKER PHOTHON III CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19803
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.078
_diffrn_reflns_theta_max         72.111
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2626
_reflns_number_gt                2485
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Bruker SHELXTL'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+0.5494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         2626
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0830
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.52528(8) -0.02853(6) 0.18219(6) 0.01892(18) Uani 1 1 d . . . . .
O2 O 0.69604(8) 0.04081(7) 0.32771(6) 0.02278(19) Uani 1 1 d . . . . .
N1 N 0.29056(9) 0.58037(8) 0.15183(7) 0.0168(2) Uani 1 1 d . . . . .
N2 N 0.69291(9) 0.48438(8) 0.40380(7) 0.0178(2) Uani 1 1 d . . . . .
C1 C 0.15426(11) 0.53611(10) 0.08877(9) 0.0207(2) Uani 1 1 d . . . . .
H10 H 0.149972 0.450401 0.099963 0.031 Uiso 1 1 calc R U . . .
H11 H 0.139417 0.552980 0.008090 0.031 Uiso 1 1 calc R U . . .
H1 H 0.081971 0.575278 0.115952 0.031 Uiso 1 1 calc R U . . .
C2 C 0.40168(11) 0.53224(9) 0.10620(9) 0.0161(2) Uani 1 1 d . . . . .
H9 H 0.484184 0.584150 0.130758 0.019 Uiso 1 1 calc R U . . .
H8 H 0.369894 0.535471 0.022586 0.019 Uiso 1 1 calc R U . . .
C3 C 0.44523(10) 0.40636(9) 0.14139(8) 0.0150(2) Uani 1 1 d . . . . .
C4 C 0.52734(10) 0.38458(9) 0.25228(8) 0.0155(2) Uani 1 1 d . . . . .
C5 C 0.57708(10) 0.27069(9) 0.28281(8) 0.0160(2) Uani 1 1 d . . . . .
H5 H 0.634708 0.256413 0.356940 0.019 Uiso 1 1 calc R U . . .
C6 C 0.54335(10) 0.17760(9) 0.20601(9) 0.0160(2) Uani 1 1 d . . . . .
C7 C 0.59909(11) 0.05810(10) 0.24568(9) 0.0166(2) Uani 1 1 d . . . . .
C8 C 0.56935(12) -0.14777(10) 0.21646(10) 0.0227(2) Uani 1 1 d . . . . .
H3 H 0.658027 -0.163820 0.199713 0.034 Uiso 1 1 calc R U . . .
H4 H 0.499115 -0.203956 0.175075 0.034 Uiso 1 1 calc R U . . .
H2 H 0.580820 -0.156494 0.297871 0.034 Uiso 1 1 calc R U . . .
C9 C 0.41118(11) 0.31203(10) 0.06546(8) 0.0164(2) Uani 1 1 d . . . . .
H6 H 0.354873 0.326113 -0.009162 0.020 Uiso 1 1 calc R U . . .
C10 C 0.45801(10) 0.19804(9) 0.09687(9) 0.0165(2) Uani 1 1 d . . . . .
H7 H 0.432348 0.134446 0.044720 0.020 Uiso 1 1 calc R U . . .
C11 C 0.31267(11) 0.55162(10) 0.27248(9) 0.0180(2) Uani 1 1 d . . . . .
H15 H 0.283700 0.468650 0.278909 0.022 Uiso 1 1 calc R U . . .
H16 H 0.252205 0.603228 0.303880 0.022 Uiso 1 1 calc R U . . .
C12 C 0.46073(11) 0.56625(9) 0.34278(8) 0.0166(2) Uani 1 1 d . . . . .
C13 C 0.56217(11) 0.48266(9) 0.33597(8) 0.0157(2) Uani 1 1 d . . . . .
C14 C 0.72672(11) 0.57293(10) 0.47865(9) 0.0195(2) Uani 1 1 d . . . . .
H14 H 0.819098 0.575706 0.526171 0.023 Uiso 1 1 calc R U . . .
C15 C 0.63528(12) 0.66087(10) 0.49112(9) 0.0207(2) Uani 1 1 d . . . . .
H12 H 0.664456 0.722623 0.544862 0.025 Uiso 1 1 calc R U . . .
C16 C 0.49970(12) 0.65601(9) 0.42268(9) 0.0193(2) Uani 1 1 d . . . . .
H13 H 0.433829 0.713793 0.430415 0.023 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 C7 1.3406(13) . ?
O1 C8 1.4433(13) . ?
O2 C7 1.2097(13) . ?
N1 C1 1.4610(13) . ?
N1 C11 1.4740(13) . ?
N1 C2 1.4769(13) . ?
N2 C14 1.3381(14) . ?
N2 C13 1.3464(14) . ?
C1 H10 0.9800 . ?
C1 H11 0.9800 . ?
C1 H1 0.9800 . ?
C2 C3 1.5147(14) . ?
C2 H9 0.9900 . ?
C2 H8 0.9900 . ?
C3 C9 1.3956(15) . ?
C3 C4 1.4082(14) . ?
C4 C5 1.3930(15) . ?
C4 C13 1.4866(14) . ?
C5 C6 1.3913(14) . ?
C5 H5 0.9500 . ?
C6 C10 1.3993(14) . ?
C6 C7 1.4903(14) . ?
C8 H3 0.9800 . ?
C8 H4 0.9800 . ?
C8 H2 0.9800 . ?
C9 C10 1.3879(15) . ?
C9 H6 0.9500 . ?
C10 H7 0.9500 . ?
C11 C12 1.5071(14) . ?
C11 H15 0.9900 . ?
C11 H16 0.9900 . ?
C12 C16 1.3908(15) . ?
C12 C13 1.4044(15) . ?
C14 C15 1.3860(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.3890(15) . ?
C15 H12 0.9500 . ?
C16 H13 0.9500 . ?

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
C7 O1 C8 115.75(8) . . ?
C1 N1 C11 108.77(8) . . ?
C1 N1 C2 111.26(8) . . ?
C11 N1 C2 112.17(8) . . ?
C14 N2 C13 117.25(9) . . ?
N1 C1 H10 109.5 . . ?
N1 C1 H11 109.5 . . ?
H10 C1 H11 109.5 . . ?
N1 C1 H1 109.5 . . ?
H10 C1 H1 109.5 . . ?
H11 C1 H1 109.5 . . ?
N1 C2 C3 115.13(8) . . ?
N1 C2 H9 108.5 . . ?
C3 C2 H9 108.5 . . ?
N1 C2 H8 108.5 . . ?
C3 C2 H8 108.5 . . ?
H9 C2 H8 107.5 . . ?
C9 C3 C4 119.06(9) . . ?
C9 C3 C2 121.75(9) . . ?
C4 C3 C2 119.14(9) . . ?
C5 C4 C3 119.57(9) . . ?
C5 C4 C13 120.12(9) . . ?
C3 C4 C13 120.30(9) . . ?
C6 C5 C4 120.77(9) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C10 119.84(10) . . ?
C5 C6 C7 117.51(9) . . ?
C10 C6 C7 122.64(9) . . ?
O2 C7 O1 123.86(10) . . ?
O2 C7 C6 124.23(10) . . ?
O1 C7 C6 111.85(9) . . ?
O1 C8 H3 109.5 . . ?
O1 C8 H4 109.5 . . ?
H3 C8 H4 109.5 . . ?
O1 C8 H2 109.5 . . ?
H3 C8 H2 109.5 . . ?
H4 C8 H2 109.5 . . ?
C10 C9 C3 121.27(9) . . ?
C10 C9 H6 119.4 . . ?
C3 C9 H6 119.4 . . ?
C9 C10 C6 119.43(9) . . ?
C9 C10 H7 120.3 . . ?
C6 C10 H7 120.3 . . ?
N1 C11 C12 114.09(9) . . ?
N1 C11 H15 108.7 . . ?
C12 C11 H15 108.7 . . ?
N1 C11 H16 108.7 . . ?
C12 C11 H16 108.7 . . ?
H15 C11 H16 107.6 . . ?
C16 C12 C13 117.57(10) . . ?
C16 C12 C11 121.86(10) . . ?
C13 C12 C11 120.36(9) . . ?
N2 C13 C12 123.32(10) . . ?
N2 C13 C4 116.40(9) . . ?
C12 C13 C4 120.27(9) . . ?
N2 C14 C15 124.04(10) . . ?
N2 C14 H14 118.0 . . ?
C15 C14 H14 118.0 . . ?
C14 C15 C16 118.01(10) . . ?
C14 C15 H12 121.0 . . ?
C16 C15 H12 121.0 . . ?
C15 C16 C12 119.77(10) . . ?
C15 C16 H13 120.1 . . ?
C12 C16 H13 120.1 . . ?

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 C2 C3 -78.45(11) . . . . ?
C11 N1 C2 C3 43.64(12) . . . . ?
N1 C2 C3 C9 108.05(11) . . . . ?
N1 C2 C3 C4 -74.74(12) . . . . ?
C9 C3 C4 C5 2.33(15) . . . . ?
C2 C3 C4 C5 -174.96(9) . . . . ?
C9 C3 C4 C13 -178.37(9) . . . . ?
C2 C3 C4 C13 4.35(14) . . . . ?
C3 C4 C5 C6 -1.83(15) . . . . ?
C13 C4 C5 C6 178.87(9) . . . . ?
C4 C5 C6 C10 -0.28(15) . . . . ?
C4 C5 C6 C7 -179.18(9) . . . . ?
C8 O1 C7 O2 -0.79(15) . . . . ?
C8 O1 C7 C6 -178.26(9) . . . . ?
C5 C6 C7 O2 -18.65(15) . . . . ?
C10 C6 C7 O2 162.48(10) . . . . ?
C5 C6 C7 O1 158.82(9) . . . . ?
C10 C6 C7 O1 -20.05(14) . . . . ?
C4 C3 C9 C10 -0.76(15) . . . . ?
C2 C3 C9 C10 176.45(9) . . . . ?
C3 C9 C10 C6 -1.33(15) . . . . ?
C5 C6 C10 C9 1.85(15) . . . . ?
C7 C6 C10 C9 -179.31(9) . . . . ?
C1 N1 C11 C12 166.39(9) . . . . ?
C2 N1 C11 C12 42.88(12) . . . . ?
N1 C11 C12 C16 110.41(11) . . . . ?
N1 C11 C12 C13 -74.96(12) . . . . ?
C14 N2 C13 C12 -1.97(15) . . . . ?
C14 N2 C13 C4 179.12(9) . . . . ?
C16 C12 C13 N2 1.22(15) . . . . ?
C11 C12 C13 N2 -173.63(9) . . . . ?
C16 C12 C13 C4 -179.91(9) . . . . ?
C11 C12 C13 C4 5.24(15) . . . . ?
C5 C4 C13 N2 40.13(14) . . . . ?
C3 C4 C13 N2 -139.17(10) . . . . ?
C5 C4 C13 C12 -138.82(10) . . . . ?
C3 C4 C13 C12 41.88(14) . . . . ?
C13 N2 C14 C15 0.93(16) . . . . ?
N2 C14 C15 C16 0.82(17) . . . . ?
C14 C15 C16 C12 -1.58(16) . . . . ?
C13 C12 C16 C15 0.63(15) . . . . ?
C11 C12 C16 C15 175.39(10) . . . . ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.043


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/ethylacetate'
_chemical_properties_physical    'Not sensitive'
