# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_D19144
_database_code_depnum_ccdc_archive 'CCDC 2000166'
loop_
_audit_author_name
_audit_author_address
'Jonathan Becker'
;Justus Liebig University Giessen
Germany
;
_audit_update_record             
;
2020-04-30 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            5
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N'
_chemical_formula_weight         223.30

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.2231(2)
_cell_length_b                   14.5123(4)
_cell_length_c                   22.3944(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2347.47(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9741
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      79.00

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.567
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.199
_exptl_absorpt_coefficient_mu    0.553
_shelx_estimated_absorpt_T_min   0.745
_shelx_estimated_absorpt_T_max   0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5855
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker PHOTON100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            58893
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.629
_diffrn_reflns_theta_max         77.310
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_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             4974
_reflns_number_gt                4827
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker D8 Venture Dual I\mS fixed chi instrument. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+0.5375P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2037 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 Absolute structure confirmed using Bayesian statistics [P3 
 (rac-twin) 0.1E-04] (Hooft, Straver, and Spek, J. Appl. Cryst. 
 (2008), 41, 96-103). 
;
_refine_ls_abs_structure_Flack   -0.12(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4974
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0818
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.78147(19) 0.55444(9) 0.42204(6) 0.0182(3) Uani 1 1 d . . . . .
C1 C 0.6947(2) 0.49888(10) 0.45712(7) 0.0156(3) Uani 1 1 d . . . . .
C2 C 0.7601(2) 0.49870(11) 0.52157(7) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.5925(2) 0.52373(11) 0.56129(7) 0.0182(3) Uani 1 1 d . . . . .
H3A H 0.629099 0.522095 0.603881 0.022 Uiso 1 1 calc R U . . .
H3AB H 0.549424 0.586809 0.551775 0.022 Uiso 1 1 calc R U . . .
C4 C 0.4354(2) 0.45417(12) 0.55000(8) 0.0200(3) Uani 1 1 d . . . . .
H4 H 0.327218 0.469681 0.575970 0.024 Uiso 1 1 calc R U . . .
C5 C 0.3763(2) 0.45804(12) 0.48409(8) 0.0214(3) Uani 1 1 d . . . . .
H5A H 0.330828 0.520652 0.474421 0.026 Uiso 1 1 calc R U . . .
H5AB H 0.273956 0.413949 0.477102 0.026 Uiso 1 1 calc R U . . .
C6 C 0.5418(2) 0.43374(11) 0.44310(7) 0.0183(3) Uani 1 1 d . . . . .
H6 H 0.505998 0.437728 0.400039 0.022 Uiso 1 1 calc R U . . .
C7 C 0.8268(2) 0.40029(11) 0.53669(7) 0.0170(3) Uani 1 1 d . . . . .
H7A H 0.935335 0.384344 0.511732 0.020 Uiso 1 1 calc R U . . .
H7AB H 0.864556 0.397117 0.579144 0.020 Uiso 1 1 calc R U . . .
C8 C 0.6691(2) 0.33186(11) 0.52491(7) 0.0187(3) Uani 1 1 d . . . . .
H8 H 0.711997 0.268102 0.534674 0.022 Uiso 1 1 calc R U . . .
C9 C 0.5034(2) 0.35659(12) 0.56471(8) 0.0222(4) Uani 1 1 d . . . . .
H9A H 0.402020 0.311830 0.558123 0.027 Uiso 1 1 calc R U . . .
H9AB H 0.540441 0.353347 0.607223 0.027 Uiso 1 1 calc R U . . .
C10 C 0.6124(2) 0.33618(11) 0.45887(7) 0.0198(3) Uani 1 1 d . . . . .
H10A H 0.513687 0.290442 0.451019 0.024 Uiso 1 1 calc R U . . .
H10B H 0.720087 0.320681 0.433425 0.024 Uiso 1 1 calc R U . . .
C11 C 0.9096(2) 0.56983(10) 0.51799(7) 0.0157(3) Uani 1 1 d . . . . .
C12 C 1.0289(2) 0.60673(11) 0.56003(7) 0.0186(3) Uani 1 1 d . . . . .
H12 H 1.025701 0.586255 0.600312 0.022 Uiso 1 1 calc R U . . .
C13 C 1.1541(2) 0.67476(12) 0.54205(8) 0.0220(3) Uani 1 1 d . . . . .
H13 H 1.234825 0.701797 0.570577 0.026 Uiso 1 1 calc R U . . .
C14 C 1.1616(2) 0.70330(12) 0.48266(8) 0.0225(3) Uani 1 1 d . . . . .
H14 H 1.248751 0.748918 0.471049 0.027 Uiso 1 1 calc R U . . .
C15 C 1.0426(2) 0.66566(11) 0.44007(8) 0.0204(3) Uani 1 1 d . . . . .
H15 H 1.047841 0.684911 0.399565 0.024 Uiso 1 1 calc R U . . .
C16 C 0.9167(2) 0.59959(11) 0.45835(7) 0.0168(3) Uani 1 1 d . . . . .
N21 N 0.34352(19) 0.26875(10) 0.34861(6) 0.0183(3) Uani 1 1 d . . . . .
C21 C 0.4330(2) 0.22445(11) 0.30810(7) 0.0157(3) Uani 1 1 d . . . . .
C22 C 0.3761(2) 0.24314(11) 0.24433(7) 0.0162(3) Uani 1 1 d . . . . .
C23 C 0.5477(2) 0.27724(11) 0.20967(7) 0.0202(3) Uani 1 1 d . . . . .
H23A H 0.515329 0.287485 0.167236 0.024 Uiso 1 1 calc R U . . .
H23B H 0.591497 0.336328 0.226666 0.024 Uiso 1 1 calc R U . . .
C24 C 0.7013(2) 0.20406(12) 0.21445(8) 0.0213(3) Uani 1 1 d . . . . .
H24 H 0.812374 0.225542 0.191711 0.026 Uiso 1 1 calc R U . . .
C25 C 0.7550(2) 0.18977(12) 0.28020(8) 0.0212(3) Uani 1 1 d . . . . .
H25A H 0.800106 0.248542 0.297290 0.025 Uiso 1 1 calc R U . . .
H25B H 0.856055 0.143895 0.282987 0.025 Uiso 1 1 calc R U . . .
C26 C 0.5848(2) 0.15559(12) 0.31597(7) 0.0190(3) Uani 1 1 d . . . . .
H26 H 0.616056 0.147454 0.359147 0.023 Uiso 1 1 calc R U . . .
C27 C 0.3074(2) 0.15083(11) 0.21769(8) 0.0202(3) Uani 1 1 d . . . . .
H27A H 0.197031 0.129148 0.239813 0.024 Uiso 1 1 calc R U . . .
H27B H 0.272316 0.159584 0.175336 0.024 Uiso 1 1 calc R U . . .
C28 C 0.4634(2) 0.07902(12) 0.22240(8) 0.0219(4) Uani 1 1 d . . . . .
H28 H 0.420048 0.019389 0.204917 0.026 Uiso 1 1 calc R U . . .
C29 C 0.6328(2) 0.11315(13) 0.18759(8) 0.0237(4) Uani 1 1 d . . . . .
H29A H 0.732500 0.066445 0.189479 0.028 Uiso 1 1 calc R U . . .
H29B H 0.599331 0.122510 0.145148 0.028 Uiso 1 1 calc R U . . .
C30 C 0.5166(2) 0.06396(12) 0.28820(8) 0.0223(3) Uani 1 1 d . . . . .
H30A H 0.615723 0.017024 0.290872 0.027 Uiso 1 1 calc R U . . .
H30B H 0.407914 0.041052 0.310672 0.027 Uiso 1 1 calc R U . . .
C31 C 0.2268(2) 0.31361(11) 0.25508(7) 0.0167(3) Uani 1 1 d . . . . .
C32 C 0.1125(2) 0.36330(12) 0.21733(7) 0.0205(3) Uani 1 1 d . . . . .
H32 H 0.120281 0.355848 0.175260 0.025 Uiso 1 1 calc R U . . .
C33 C -0.0147(3) 0.42468(12) 0.24248(8) 0.0223(4) Uani 1 1 d . . . . .
H33 H -0.093660 0.459548 0.217162 0.027 Uiso 1 1 calc R U . . .
C34 C -0.0272(2) 0.43538(12) 0.30414(8) 0.0221(4) Uani 1 1 d . . . . .
H34 H -0.115037 0.477215 0.320350 0.027 Uiso 1 1 calc R U . . .
C35 C 0.0874(2) 0.38552(12) 0.34240(7) 0.0207(3) Uani 1 1 d . . . . .
H35 H 0.079383 0.392739 0.384486 0.025 Uiso 1 1 calc R U . . .
C36 C 0.2135(2) 0.32504(11) 0.31702(7) 0.0171(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.289(2) . ?
N1 C16 1.430(2) . ?
C1 C6 1.487(2) . ?
C1 C2 1.519(2) . ?
C2 C11 1.496(2) . ?
C2 C7 1.545(2) . ?
C2 C3 1.546(2) . ?
C3 C4 1.539(2) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C9 1.535(2) . ?
C4 C5 1.538(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.548(2) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C10 1.546(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.534(2) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C9 1.535(2) . ?
C8 C10 1.536(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.384(2) . ?
C11 C16 1.404(2) . ?
C12 C13 1.398(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.394(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(2) . ?
C15 H15 0.9500 . ?
N21 C21 1.286(2) . ?
N21 C36 1.432(2) . ?
C21 C26 1.494(2) . ?
C21 C22 1.511(2) . ?
C22 C31 1.505(2) . ?
C22 C23 1.544(2) . ?
C22 C27 1.548(2) . ?
C23 C24 1.539(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C29 1.532(2) . ?
C24 C25 1.537(2) . ?
C24 H24 1.0000 . ?
C25 C26 1.549(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C30 1.549(2) . ?
C26 H26 1.0000 . ?
C27 C28 1.538(2) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.533(2) . ?
C28 C30 1.538(2) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.385(2) . ?
C31 C36 1.400(2) . ?
C32 C33 1.398(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.393(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.394(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.387(2) . ?
C35 H35 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
C1 N1 C16 105.80(13) . . ?
N1 C1 C6 129.07(15) . . ?
N1 C1 C2 115.41(14) . . ?
C6 C1 C2 115.51(13) . . ?
C11 C2 C1 99.93(12) . . ?
C11 C2 C7 115.11(13) . . ?
C1 C2 C7 107.88(12) . . ?
C11 C2 C3 115.73(13) . . ?
C1 C2 C3 107.62(12) . . ?
C7 C2 C3 109.61(13) . . ?
C4 C3 C2 109.18(13) . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3AB 109.8 . . ?
C2 C3 H3AB 109.8 . . ?
H3A C3 H3AB 108.3 . . ?
C9 C4 C5 109.19(14) . . ?
C9 C4 C3 109.52(13) . . ?
C5 C4 C3 109.79(13) . . ?
C9 C4 H4 109.4 . . ?
C5 C4 H4 109.4 . . ?
C3 C4 H4 109.4 . . ?
C4 C5 C6 110.25(13) . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5AB 109.6 . . ?
C6 C5 H5AB 109.6 . . ?
H5A C5 H5AB 108.1 . . ?
C1 C6 C10 106.79(13) . . ?
C1 C6 C5 107.66(13) . . ?
C10 C6 C5 109.15(14) . . ?
C1 C6 H6 111.0 . . ?
C10 C6 H6 111.0 . . ?
C5 C6 H6 111.0 . . ?
C8 C7 C2 109.20(12) . . ?
C8 C7 H7A 109.8 . . ?
C2 C7 H7A 109.8 . . ?
C8 C7 H7AB 109.8 . . ?
C2 C7 H7AB 109.8 . . ?
H7A C7 H7AB 108.3 . . ?
C7 C8 C9 109.13(13) . . ?
C7 C8 C10 109.70(13) . . ?
C9 C8 C10 110.00(13) . . ?
C7 C8 H8 109.3 . . ?
C9 C8 H8 109.3 . . ?
C10 C8 H8 109.3 . . ?
C4 C9 C8 109.91(13) . . ?
C4 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C4 C9 H9AB 109.7 . . ?
C8 C9 H9AB 109.7 . . ?
H9A C9 H9AB 108.2 . . ?
C8 C10 C6 110.21(13) . . ?
C8 C10 H10A 109.6 . . ?
C6 C10 H10A 109.6 . . ?
C8 C10 H10B 109.6 . . ?
C6 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C16 120.35(15) . . ?
C12 C11 C2 132.82(15) . . ?
C16 C11 C2 106.83(13) . . ?
C11 C12 C13 118.67(15) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C14 C13 C12 120.65(16) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.79(16) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 118.29(15) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
C15 C16 C11 121.23(15) . . ?
C15 C16 N1 126.74(15) . . ?
C11 C16 N1 112.02(14) . . ?
C21 N21 C36 105.45(13) . . ?
N21 C21 C26 128.32(14) . . ?
N21 C21 C22 116.11(14) . . ?
C26 C21 C22 115.57(13) . . ?
C31 C22 C21 99.55(12) . . ?
C31 C22 C23 115.96(13) . . ?
C21 C22 C23 108.29(13) . . ?
C31 C22 C27 114.84(13) . . ?
C21 C22 C27 107.23(13) . . ?
C23 C22 C27 109.93(13) . . ?
C24 C23 C22 108.82(13) . . ?
C24 C23 H23A 109.9 . . ?
C22 C23 H23A 109.9 . . ?
C24 C23 H23B 109.9 . . ?
C22 C23 H23B 109.9 . . ?
H23A C23 H23B 108.3 . . ?
C29 C24 C25 109.97(14) . . ?
C29 C24 C23 109.50(14) . . ?
C25 C24 C23 109.97(14) . . ?
C29 C24 H24 109.1 . . ?
C25 C24 H24 109.1 . . ?
C23 C24 H24 109.1 . . ?
C24 C25 C26 109.79(13) . . ?
C24 C25 H25A 109.7 . . ?
C26 C25 H25A 109.7 . . ?
C24 C25 H25B 109.7 . . ?
C26 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
C21 C26 C30 107.08(14) . . ?
C21 C26 C25 107.89(13) . . ?
C30 C26 C25 108.65(13) . . ?
C21 C26 H26 111.0 . . ?
C30 C26 H26 111.0 . . ?
C25 C26 H26 111.0 . . ?
C28 C27 C22 108.98(13) . . ?
C28 C27 H27A 109.9 . . ?
C22 C27 H27A 109.9 . . ?
C28 C27 H27B 109.9 . . ?
C22 C27 H27B 109.9 . . ?
H27A C27 H27B 108.3 . . ?
C29 C28 C27 109.31(14) . . ?
C29 C28 C30 109.48(14) . . ?
C27 C28 C30 110.18(14) . . ?
C29 C28 H28 109.3 . . ?
C27 C28 H28 109.3 . . ?
C30 C28 H28 109.3 . . ?
C24 C29 C28 109.66(14) . . ?
C24 C29 H29A 109.7 . . ?
C28 C29 H29A 109.7 . . ?
C24 C29 H29B 109.7 . . ?
C28 C29 H29B 109.7 . . ?
H29A C29 H29B 108.2 . . ?
C28 C30 C26 110.01(14) . . ?
C28 C30 H30A 109.7 . . ?
C26 C30 H30A 109.7 . . ?
C28 C30 H30B 109.7 . . ?
C26 C30 H30B 109.7 . . ?
H30A C30 H30B 108.2 . . ?
C32 C31 C36 120.14(15) . . ?
C32 C31 C22 133.11(15) . . ?
C36 C31 C22 106.75(14) . . ?
C31 C32 C33 118.55(15) . . ?
C31 C32 H32 120.7 . . ?
C33 C32 H32 120.7 . . ?
C34 C33 C32 120.87(16) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C35 120.87(16) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C36 C35 C34 117.82(15) . . ?
C36 C35 H35 121.1 . . ?
C34 C35 H35 121.1 . . ?
C35 C36 C31 121.75(15) . . ?
C35 C36 N21 126.12(15) . . ?
C31 C36 N21 112.13(14) . . ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.037


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_D19274
_database_code_depnum_ccdc_archive 'CCDC 2000167'
loop_
_audit_author_name
_audit_author_address
'Jonathan Becker'
;Justus Liebig University Giessen
Germany
;
_audit_update_record             
;
2020-04-30 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            8
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 N O'
_chemical_formula_weight         296.42

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   27.1498(9)
_cell_length_b                   10.3031(3)
_cell_length_c                   11.3085(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.1403(16)
_cell_angle_gamma                90
_cell_volume                     3162.67(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9031
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      32.02

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.331
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6786
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker PHOTON100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            63246
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.114
_diffrn_reflns_theta_max         31.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5274
_reflns_number_gt                4204
_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       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker D8 Venture Dual I\mS fixed chi instrument. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0701P)²+1.9108P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5274
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.29896(3) 0.84032(7) 0.27799(7) 0.02250(17) Uani 1 1 d . . . . .
N1 N 0.32444(3) 0.74182(8) 0.31289(7) 0.01454(16) Uani 1 1 d . . . . .
C1 C 0.30008(3) 0.61256(9) 0.29975(8) 0.01447(17) Uani 1 1 d . . . . .
C2 C 0.25367(4) 0.61427(10) 0.37592(9) 0.01862(19) Uani 1 1 d . . . . .
H2A H 0.232847 0.688071 0.352765 0.028 Uiso 1 1 calc R U . . .
H2B H 0.263368 0.622483 0.459524 0.028 Uiso 1 1 calc R U . . .
H2C H 0.235266 0.533352 0.363936 0.028 Uiso 1 1 calc R U . . .
C3 C 0.28446(4) 0.59478(10) 0.16863(9) 0.0198(2) Uani 1 1 d . . . . .
H3A H 0.266608 0.672084 0.141075 0.030 Uiso 1 1 calc R U . . .
H3B H 0.263048 0.518578 0.160739 0.030 Uiso 1 1 calc R U . . .
H3C H 0.313829 0.582408 0.120893 0.030 Uiso 1 1 calc R U . . .
C4 C 0.33467(3) 0.50339(9) 0.33898(8) 0.01367(17) Uani 1 1 d . . . . .
C5 C 0.31759(4) 0.37621(10) 0.32466(9) 0.01658(18) Uani 1 1 d . . . . .
H5 H 0.285094 0.361902 0.294746 0.020 Uiso 1 1 calc R U . . .
C6 C 0.34717(4) 0.27049(10) 0.35328(9) 0.01805(19) Uani 1 1 d . . . . .
H6 H 0.334698 0.184732 0.345173 0.022 Uiso 1 1 calc R U . . .
C7 C 0.39519(4) 0.29107(10) 0.39390(9) 0.01869(19) Uani 1 1 d . . . . .
H7 H 0.416324 0.219387 0.409643 0.022 Uiso 1 1 calc R U . . .
C8 C 0.41211(4) 0.41698(10) 0.41138(9) 0.01758(19) Uani 1 1 d . . . . .
H8 H 0.444780 0.430308 0.440529 0.021 Uiso 1 1 calc R U . . .
C9 C 0.38216(3) 0.52471(9) 0.38703(8) 0.01391(17) Uani 1 1 d . . . . .
C10 C 0.39897(4) 0.72756(11) 0.19829(9) 0.0201(2) Uani 1 1 d . . . . .
H10A H 0.392436 0.636557 0.178219 0.030 Uiso 1 1 calc R U . . .
H10B H 0.434557 0.743411 0.198301 0.030 Uiso 1 1 calc R U . . .
H10C H 0.382665 0.783932 0.139707 0.030 Uiso 1 1 calc R U . . .
C11 C 0.37894(3) 0.75702(9) 0.32169(8) 0.01398(17) Uani 1 1 d . . . . .
C12 C 0.39825(3) 0.66187(9) 0.41816(8) 0.01318(17) Uani 1 1 d . . . . .
C13 C 0.37545(4) 0.69782(9) 0.53915(8) 0.01593(18) Uani 1 1 d . . . . .
H13A H 0.339203 0.687901 0.533692 0.019 Uiso 1 1 calc R U . . .
H13B H 0.388086 0.637688 0.600924 0.019 Uiso 1 1 calc R U . . .
C14 C 0.38820(4) 0.83753(10) 0.57415(9) 0.01850(19) Uani 1 1 d . . . . .
H14 H 0.372857 0.858415 0.651528 0.022 Uiso 1 1 calc R U . . .
C15 C 0.36798(4) 0.93009(10) 0.47870(9) 0.01807(19) Uani 1 1 d . . . . .
H15A H 0.375783 1.020864 0.500842 0.022 Uiso 1 1 calc R U . . .
H15B H 0.331718 0.921342 0.472128 0.022 Uiso 1 1 calc R U . . .
C16 C 0.39109(4) 0.89784(9) 0.35948(9) 0.01647(18) Uani 1 1 d . . . . .
H16 H 0.378267 0.959377 0.297797 0.020 Uiso 1 1 calc R U . . .
C17 C 0.44731(4) 0.91326(10) 0.37265(10) 0.0206(2) Uani 1 1 d . . . . .
H17A H 0.462923 0.895034 0.296042 0.025 Uiso 1 1 calc R U . . .
H17B H 0.455396 1.003597 0.395693 0.025 Uiso 1 1 calc R U . . .
C18 C 0.46733(4) 0.81932(11) 0.46693(10) 0.0210(2) Uani 1 1 d . . . . .
H18 H 0.503925 0.828753 0.473942 0.025 Uiso 1 1 calc R U . . .
C19 C 0.45443(4) 0.67853(10) 0.43289(9) 0.01853(19) Uani 1 1 d . . . . .
H19A H 0.467001 0.618835 0.495097 0.022 Uiso 1 1 calc R U . . .
H19B H 0.470534 0.655879 0.357875 0.022 Uiso 1 1 calc R U . . .
C20 C 0.44422(4) 0.85188(11) 0.58604(10) 0.0228(2) Uani 1 1 d . . . . .
H20A H 0.457167 0.792404 0.647996 0.027 Uiso 1 1 calc R U . . .
H20B H 0.452749 0.941885 0.609286 0.027 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 N1 1.2860(10) . ?
N1 C11 1.4892(12) . ?
N1 C1 1.4931(12) . ?
C1 C4 1.5256(13) . ?
C1 C2 1.5406(14) . ?
C1 C3 1.5450(13) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.3982(13) . ?
C4 C9 1.4065(13) . ?
C5 C6 1.3878(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.3898(14) . ?
C6 H6 0.9500 . ?
C7 C8 1.3891(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.4000(13) . ?
C8 H8 0.9500 . ?
C9 C12 1.5185(13) . ?
C10 C11 1.5380(13) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.5463(13) . ?
C11 C12 1.5503(13) . ?
C12 C19 1.5405(13) . ?
C12 C13 1.5578(13) . ?
C13 C14 1.5307(14) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C20 1.5315(15) . ?
C14 C15 1.5337(15) . ?
C14 H14 1.0000 . ?
C15 C16 1.5347(14) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5389(14) . ?
C16 H16 1.0000 . ?
C17 C18 1.5317(16) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C20 1.5343(16) . ?
C18 C19 1.5394(15) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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 N1 C11 117.74(8) . . ?
O1 N1 C1 116.02(7) . . ?
C11 N1 C1 122.55(7) . . ?
N1 C1 C4 111.09(7) . . ?
N1 C1 C2 107.45(8) . . ?
C4 C1 C2 110.57(8) . . ?
N1 C1 C3 108.29(8) . . ?
C4 C1 C3 110.32(8) . . ?
C2 C1 C3 109.03(8) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C9 119.37(8) . . ?
C5 C4 C1 117.16(8) . . ?
C9 C4 C1 123.47(8) . . ?
C6 C5 C4 121.29(9) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 119.47(9) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 119.67(9) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 121.54(9) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C4 118.46(9) . . ?
C8 C9 C12 121.93(8) . . ?
C4 C9 C12 119.49(8) . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C10 106.70(8) . . ?
N1 C11 C16 108.86(8) . . ?
C10 C11 C16 111.02(8) . . ?
N1 C11 C12 107.59(7) . . ?
C10 C11 C12 113.14(8) . . ?
C16 C11 C12 109.37(7) . . ?
C9 C12 C19 114.11(8) . . ?
C9 C12 C11 109.49(7) . . ?
C19 C12 C11 109.02(8) . . ?
C9 C12 C13 107.90(7) . . ?
C19 C12 C13 106.77(7) . . ?
C11 C12 C13 109.44(7) . . ?
C14 C13 C12 111.04(8) . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C20 109.43(9) . . ?
C13 C14 C15 109.08(8) . . ?
C20 C14 C15 110.04(8) . . ?
C13 C14 H14 109.4 . . ?
C20 C14 H14 109.4 . . ?
C15 C14 H14 109.4 . . ?
C14 C15 C16 109.68(8) . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C15 C16 C17 108.34(8) . . ?
C15 C16 C11 110.93(8) . . ?
C17 C16 C11 109.23(8) . . ?
C15 C16 H16 109.4 . . ?
C17 C16 H16 109.4 . . ?
C11 C16 H16 109.4 . . ?
C18 C17 C16 109.86(8) . . ?
C18 C17 H17A 109.7 . . ?
C16 C17 H17A 109.7 . . ?
C18 C17 H17B 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C17 C18 C20 109.11(9) . . ?
C17 C18 C19 110.22(8) . . ?
C20 C18 C19 109.31(9) . . ?
C17 C18 H18 109.4 . . ?
C20 C18 H18 109.4 . . ?
C19 C18 H18 109.4 . . ?
C18 C19 C12 110.60(8) . . ?
C18 C19 H19A 109.5 . . ?
C12 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C12 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C14 C20 C18 108.93(8) . . ?
C14 C20 H20A 109.9 . . ?
C18 C20 H20A 109.9 . . ?
C14 C20 H20B 109.9 . . ?
C18 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.060


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
