# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_stu10239
_database_code_depnum_ccdc_archive 'CCDC 2178219'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2022-06-10 deposited with the CCDC.	2022-08-05 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2021.4-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         295.37

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.0815(2)
_cell_length_b                   11.6927(2)
_cell_length_c                   14.7988(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.0500(10)
_cell_angle_gamma                90
_cell_volume                     1536.82(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9923
_cell_measurement_theta_min      4.8623
_cell_measurement_theta_max      68.2695
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632

_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          'single crystal'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            33198
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_theta_min         4.86
_diffrn_reflns_theta_max         68.26
_diffrn_reflns_theta_full        67.68
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_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.

The hydrogen at O2 atom was refined freely.
;

_reflns_number_total             2798
_reflns_number_gt                2405
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0861
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_number_reflns         2798
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+0.7314P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.195
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX4 v2021.4-0 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1242)'
_computing_publication_material  'SHELXT 2018/2 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.55230(11) 0.57783(9) 0.40851(7) 0.0150(2) Uani d . . . 1 . .
O O1 0.45581(9) 0.63768(7) 0.45628(6) 0.0151(2) Uani d . . . 1 . .
O O2 0.61107(10) 0.63202(8) 0.60283(6) 0.0160(2) Uani d . . . 1 . .
H H2 0.551(2) 0.5717(18) 0.6073(13) 0.045(5) Uiso d . . . 1 . .
C C1 1.06771(16) 0.34902(12) 0.22168(9) 0.0235(3) Uani d . . . 1 . .
H H1A 1.053758 0.376762 0.157968 0.035000 Uiso calc U . R 1 . .
H H1B 1.038765 0.268258 0.221342 0.035000 Uiso calc U . R 1 . .
H H1C 1.173666 0.357262 0.252565 0.035000 Uiso calc U . R 1 . .
C C2 0.97080(15) 0.41787(11) 0.27267(9) 0.0180(3) Uani d . . . 1 . .
C C3 0.81422(15) 0.40941(11) 0.24859(9) 0.0195(3) Uani d . . . 1 . .
H H3 0.769602 0.359623 0.199788 0.023000 Uiso calc U . R 1 . .
C C4 0.72250(14) 0.47164(11) 0.29398(9) 0.0182(3) Uani d . . . 1 . .
H H4 0.616221 0.464260 0.276016 0.022000 Uiso calc U . R 1 . .
C C5 0.78508(14) 0.54550(11) 0.36626(8) 0.0154(3) Uani d . . . 1 . .
C C6 0.94160(14) 0.55520(11) 0.39013(9) 0.0168(3) Uani d . . . 1 . .
H H6 0.986262 0.605653 0.438432 0.020000 Uiso calc U . R 1 . .
C C7 1.03310(15) 0.49198(11) 0.34415(9) 0.0181(3) Uani d . . . 1 . .
H H7 1.139409 0.499454 0.361731 0.022000 Uiso calc U . R 1 . .
C C8 0.68920(14) 0.61237(10) 0.41709(8) 0.0147(3) Uani d . . . 1 . .
C C9 0.75710(14) 0.71302(11) 0.47388(9) 0.0158(3) Uani d . . . 1 . .
H H9A 0.814371 0.759593 0.437175 0.019000 Uiso calc U . R 1 . .
H H9B 0.828912 0.684928 0.529186 0.019000 Uiso calc U . R 1 . .
C C10 0.63951(13) 0.78880(10) 0.50483(9) 0.0154(3) Uani d . . . 1 . .
C C11 0.52789(13) 0.70488(10) 0.53564(8) 0.0146(3) Uani d . . . 1 . .
C C12 0.55850(14) 0.86213(11) 0.42376(9) 0.0188(3) Uani d . . . 1 . .
H H12A 0.629645 0.916956 0.406687 0.028000 Uiso calc U . R 1 . .
H H12B 0.475491 0.903615 0.441931 0.028000 Uiso calc U . R 1 . .
H H12C 0.518539 0.812741 0.370821 0.028000 Uiso calc U . R 1 . .
C C13 0.71819(14) 0.86640(11) 0.58365(9) 0.0183(3) Uani d . . . 1 . .
H H13A 0.767288 0.819314 0.636122 0.027000 Uiso calc U . R 1 . .
H H13B 0.643685 0.916415 0.602809 0.027000 Uiso calc U . R 1 . .
H H13C 0.793946 0.913117 0.562433 0.027000 Uiso calc U . R 1 . .
C C14 0.39915(14) 0.76193(10) 0.57008(9) 0.0154(3) Uani d . . . 1 . .
C C15 0.25874(14) 0.78111(11) 0.51322(9) 0.0187(3) Uani d . . . 1 . .
H H15 0.239903 0.757149 0.450517 0.022000 Uiso calc U . R 1 . .
C C16 0.14576(14) 0.83533(12) 0.54795(9) 0.0218(3) Uani d . . . 1 . .
H H16 0.050249 0.848186 0.508654 0.026000 Uiso calc U . R 1 . .
C C17 0.17124(15) 0.87070(12) 0.63920(9) 0.0212(3) Uani d . . . 1 . .
H H17 0.093353 0.906939 0.662632 0.025000 Uiso calc U . R 1 . .
C C18 0.31129(15) 0.85283(12) 0.69614(9) 0.0210(3) Uani d . . . 1 . .
H H18 0.329965 0.877883 0.758557 0.025000 Uiso calc U . R 1 . .
C C19 0.42429(14) 0.79836(11) 0.66203(9) 0.0184(3) Uani d . . . 1 . .
H H19 0.519636 0.785729 0.701580 0.022000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C8 . 1.2881(16) ?
N1 O1 . 1.4198(13) ?
O1 C11 . 1.4507(14) ?
O2 C11 . 1.4041(14) ?
O2 H2 . 0.90(2) ?
C1 C2 . 1.5064(18) ?
C1 H1A . 0.980000 ?
C1 H1B . 0.980000 ?
C1 H1C . 0.980000 ?
C2 C7 . 1.3929(19) ?
C2 C3 . 1.3954(19) ?
C3 C4 . 1.3813(18) ?
C3 H3 . 0.950000 ?
C4 C5 . 1.3997(18) ?
C4 H4 . 0.950000 ?
C5 C6 . 1.3958(18) ?
C5 C8 . 1.4862(17) ?
C6 C7 . 1.3914(18) ?
C6 H6 . 0.950000 ?
C7 H7 . 0.950000 ?
C8 C9 . 1.5018(17) ?
C9 C10 . 1.5295(17) ?
C9 H9A . 0.990000 ?
C9 H9B . 0.990000 ?
C10 C13 . 1.5318(17) ?
C10 C12 . 1.5321(17) ?
C10 C11 . 1.5463(17) ?
C11 C14 . 1.5232(17) ?
C12 H12A . 0.980000 ?
C12 H12B . 0.980000 ?
C12 H12C . 0.980000 ?
C13 H13A . 0.980000 ?
C13 H13B . 0.980000 ?
C13 H13C . 0.980000 ?
C14 C15 . 1.3916(18) ?
C14 C19 . 1.3984(18) ?
C15 C16 . 1.3925(18) ?
C15 H15 . 0.950000 ?
C16 C17 . 1.3848(19) ?
C16 H16 . 0.950000 ?
C17 C18 . 1.3870(19) ?
C17 H17 . 0.950000 ?
C18 C19 . 1.3892(19) ?
C18 H18 . 0.950000 ?
C19 H19 . 0.950000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 N1 O1 . . 118.67(10) ?
N1 O1 C11 . . 116.68(8) ?
C11 O2 H2 . . 106.5(12) ?
C2 C1 H1A . . 109.500000 ?
C2 C1 H1B . . 109.500000 ?
H1A C1 H1B . . 109.500000 ?
C2 C1 H1C . . 109.500000 ?
H1A C1 H1C . . 109.500000 ?
H1B C1 H1C . . 109.500000 ?
C7 C2 C3 . . 117.95(12) ?
C7 C2 C1 . . 121.71(12) ?
C3 C2 C1 . . 120.34(12) ?
C4 C3 C2 . . 121.62(12) ?
C4 C3 H3 . . 119.200000 ?
C2 C3 H3 . . 119.200000 ?
C3 C4 C5 . . 120.45(12) ?
C3 C4 H4 . . 119.800000 ?
C5 C4 H4 . . 119.800000 ?
C6 C5 C4 . . 118.24(11) ?
C6 C5 C8 . . 120.16(11) ?
C4 C5 C8 . . 121.60(11) ?
C7 C6 C5 . . 120.91(12) ?
C7 C6 H6 . . 119.500000 ?
C5 C6 H6 . . 119.500000 ?
C6 C7 C2 . . 120.83(12) ?
C6 C7 H7 . . 119.600000 ?
C2 C7 H7 . . 119.600000 ?
N1 C8 C5 . . 116.15(11) ?
N1 C8 C9 . . 125.17(11) ?
C5 C8 C9 . . 118.69(10) ?
C8 C9 C10 . . 113.00(10) ?
C8 C9 H9A . . 109.000000 ?
C10 C9 H9A . . 109.000000 ?
C8 C9 H9B . . 109.000000 ?
C10 C9 H9B . . 109.000000 ?
H9A C9 H9B . . 107.800000 ?
C9 C10 C13 . . 109.10(10) ?
C9 C10 C12 . . 109.93(10) ?
C13 C10 C12 . . 109.64(10) ?
C9 C10 C11 . . 105.21(10) ?
C13 C10 C11 . . 112.44(10) ?
C12 C10 C11 . . 110.42(10) ?
O2 C11 O1 . . 109.25(9) ?
O2 C11 C14 . . 111.46(10) ?
O1 C11 C14 . . 105.07(9) ?
O2 C11 C10 . . 107.76(9) ?
O1 C11 C10 . . 108.53(9) ?
C14 C11 C10 . . 114.65(10) ?
C10 C12 H12A . . 109.500000 ?
C10 C12 H12B . . 109.500000 ?
H12A C12 H12B . . 109.500000 ?
C10 C12 H12C . . 109.500000 ?
H12A C12 H12C . . 109.500000 ?
H12B C12 H12C . . 109.500000 ?
C10 C13 H13A . . 109.500000 ?
C10 C13 H13B . . 109.500000 ?
H13A C13 H13B . . 109.500000 ?
C10 C13 H13C . . 109.500000 ?
H13A C13 H13C . . 109.500000 ?
H13B C13 H13C . . 109.500000 ?
C15 C14 C19 . . 118.83(12) ?
C15 C14 C11 . . 122.60(11) ?
C19 C14 C11 . . 118.56(11) ?
C14 C15 C16 . . 120.20(12) ?
C14 C15 H15 . . 119.900000 ?
C16 C15 H15 . . 119.900000 ?
C17 C16 C15 . . 120.66(12) ?
C17 C16 H16 . . 119.700000 ?
C15 C16 H16 . . 119.700000 ?
C16 C17 C18 . . 119.52(12) ?
C16 C17 H17 . . 120.200000 ?
C18 C17 H17 . . 120.200000 ?
C17 C18 C19 . . 120.11(12) ?
C17 C18 H18 . . 119.900000 ?
C19 C18 H18 . . 119.900000 ?
C18 C19 C14 . . 120.68(12) ?
C18 C19 H19 . . 119.700000 ?
C14 C19 H19 . . 119.700000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 N1 O1 C11 . . . . -21.75(14) ?
C7 C2 C3 C4 . . . . -0.34(19) ?
C1 C2 C3 C4 . . . . -179.87(12) ?
C2 C3 C4 C5 . . . . -0.1(2) ?
C3 C4 C5 C6 . . . . 0.71(18) ?
C3 C4 C5 C8 . . . . -179.21(11) ?
C4 C5 C6 C7 . . . . -0.85(18) ?
C8 C5 C6 C7 . . . . 179.06(11) ?
C5 C6 C7 C2 . . . . 0.41(19) ?
C3 C2 C7 C6 . . . . 0.19(19) ?
C1 C2 C7 C6 . . . . 179.72(12) ?
O1 N1 C8 C5 . . . . 179.35(9) ?
O1 N1 C8 C9 . . . . -0.44(18) ?
C6 C5 C8 N1 . . . . -162.44(11) ?
C4 C5 C8 N1 . . . . 17.47(17) ?
C6 C5 C8 C9 . . . . 17.36(17) ?
C4 C5 C8 C9 . . . . -162.73(11) ?
N1 C8 C9 C10 . . . . -12.77(17) ?
C5 C8 C9 C10 . . . . 167.44(10) ?
C8 C9 C10 C13 . . . . 163.56(10) ?
C8 C9 C10 C12 . . . . -76.17(13) ?
C8 C9 C10 C11 . . . . 42.72(13) ?
N1 O1 C11 O2 . . . . -62.37(12) ?
N1 O1 C11 C14 . . . . 177.94(9) ?
N1 O1 C11 C10 . . . . 54.87(12) ?
C9 C10 C11 O2 . . . . 55.12(12) ?
C13 C10 C11 O2 . . . . -63.51(13) ?
C12 C10 C11 O2 . . . . 173.69(10) ?
C9 C10 C11 O1 . . . . -63.07(11) ?
C13 C10 C11 O1 . . . . 178.30(10) ?
C12 C10 C11 O1 . . . . 55.50(12) ?
C9 C10 C11 C14 . . . . 179.84(10) ?
C13 C10 C11 C14 . . . . 61.21(13) ?
C12 C10 C11 C14 . . . . -61.59(13) ?
O2 C11 C14 C15 . . . . -142.08(12) ?
O1 C11 C14 C15 . . . . -23.87(15) ?
C10 C11 C14 C15 . . . . 95.18(14) ?
O2 C11 C14 C19 . . . . 39.19(15) ?
O1 C11 C14 C19 . . . . 157.40(11) ?
C10 C11 C14 C19 . . . . -83.55(14) ?
C19 C14 C15 C16 . . . . -0.23(19) ?
C11 C14 C15 C16 . . . . -178.95(12) ?
C14 C15 C16 C17 . . . . -0.1(2) ?
C15 C16 C17 C18 . . . . 0.6(2) ?
C16 C17 C18 C19 . . . . -0.9(2) ?
C17 C18 C19 C14 . . . . 0.6(2) ?
C15 C14 C19 C18 . . . . -0.05(19) ?
C11 C14 C19 C18 . . . . 178.73(12) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 N1 3_666 0.90(2) 1.98(2) 2.8541(14) 164.5(17) ?
O2 H2 O1 3_666 0.90(2) 2.62(2) 3.2949(12) 132.5(15) ?

