# Electronic Supplementary Material (ESI) for ChemComm.
# 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_nova1
_database_code_depnum_ccdc_archive 'CCDC 1962315'
loop_
_audit_author_name
_audit_author_address
'Dr. Khalil Abboud'
;University of Florida
United States of America
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2020-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 N3 O2'
_chemical_formula_weight         323.39

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.5708(2)
_cell_length_b                   17.0112(4)
_cell_length_c                   12.3358(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.2848(6)
_cell_angle_gamma                90
_cell_volume                     1726.40(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    9998
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      36.06

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?

_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             688

_exptl_transmission_factor_min   0.7122
_exptl_transmission_factor_max   0.7471

_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9799
_exptl_absorpt_correction_T_max  0.9938

_exptl_absorpt_process_details   
'based on measured indexed crystal faces, Bruker SHELXTL2014 (Sheldrick, 2014)'

_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 DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            55483
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.096
_diffrn_reflns_theta_max         36.362
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8378
_reflns_number_gt                6168
_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 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2014)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_structure_refinement  'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2014'
_computing_publication_material  'SHELXL2014/7, Sheldrick, G. M. 2014'

_refine_special_details          
;
All H atoms were positioned geometrically ( C---H = 0.93/1.00 Å) and   
allowed to ride with Uiso(H)= 1.2/1.5Ueq(C).
Methyl ones were allowed to rotate around the corresponding C---C.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0712P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8378
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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 0.30558(7) 0.17411(3) 0.87153(4) 0.02211(12) Uani 1 1 d . . . . .
O2 O 0.18742(6) 0.16897(3) 0.68080(4) 0.01403(9) Uani 1 1 d . . . . .
N1 N 0.38774(7) 0.25384(3) 0.75120(4) 0.01275(10) Uani 1 1 d . . . . .
N2 N 0.29480(11) 0.56340(5) 0.50804(6) 0.03385(18) Uani 1 1 d . . . . .
N3 N 0.46918(8) 0.59273(4) 0.87681(6) 0.02337(14) Uani 1 1 d . . . . .
C1 C 0.57867(9) 0.29585(5) 0.66238(6) 0.02023(14) Uani 1 1 d . . . . .
H1A H 0.6269 0.2484 0.6382 0.024 Uiso 1 1 calc R U . . .
H1B H 0.6019 0.3418 0.6202 0.024 Uiso 1 1 calc R U . . .
C2 C 0.64656(9) 0.30860(5) 0.79027(7) 0.02037(14) Uani 1 1 d . . . . .
H2A H 0.6984 0.3609 0.8066 0.024 Uiso 1 1 calc R U . . .
H2B H 0.7277 0.2677 0.8243 0.024 Uiso 1 1 calc R U . . .
C3 C 0.49729(8) 0.30274(4) 0.83610(5) 0.01345(11) Uani 1 1 d . . . . .
H3A H 0.5253 0.2776 0.9124 0.016 Uiso 1 1 calc R U . . .
C4 C 0.41650(8) 0.38402(4) 0.83660(5) 0.01259(11) Uani 1 1 d . . . . .
H4A H 0.4973 0.4192 0.8885 0.015 Uiso 1 1 calc R U . . .
C5 C 0.26349(8) 0.38064(4) 0.87884(5) 0.01507(12) Uani 1 1 d . . . . .
H5A H 0.2918 0.3496 0.9496 0.018 Uiso 1 1 calc R U . . .
H5B H 0.2409 0.4349 0.8992 0.018 Uiso 1 1 calc R U . . .
C6 C 0.10659(9) 0.34776(4) 0.80419(6) 0.01742(13) Uani 1 1 d . . . . .
H6A H 0.0348 0.3290 0.8447 0.021 Uiso 1 1 calc R U . . .
C7 C 0.04880(9) 0.33990(4) 0.69232(6) 0.01896(13) Uani 1 1 d . . . . .
H7A H -0.0574 0.3181 0.6682 0.023 Uiso 1 1 calc R U . . .
C8 C 0.12066(9) 0.35910(4) 0.59743(5) 0.01893(13) Uani 1 1 d . . . . .
H8A H 0.0730 0.4096 0.5642 0.023 Uiso 1 1 calc R U . . .
H8B H 0.0830 0.3184 0.5385 0.023 Uiso 1 1 calc R U . . .
C9 C 0.30700(9) 0.36584(4) 0.62145(5) 0.01506(12) Uani 1 1 d . . . . .
H9A H 0.3299 0.3901 0.5537 0.018 Uiso 1 1 calc R U . . .
C10 C 0.39420(8) 0.28548(4) 0.64235(5) 0.01447(12) Uani 1 1 d . . . . .
H10A H 0.3475 0.2478 0.5794 0.017 Uiso 1 1 calc R U . . .
C11 C 0.37400(8) 0.41971(4) 0.72017(5) 0.01282(11) Uani 1 1 d . . . . .
C12 C 0.38512(8) 0.49828(4) 0.70560(5) 0.01464(12) Uani 1 1 d . . . . .
C13 C 0.33709(10) 0.53442(4) 0.59571(6) 0.02037(14) Uani 1 1 d . . . . .
C14 C 0.43482(9) 0.55106(4) 0.80017(6) 0.01678(12) Uani 1 1 d . . . . .
C15 C 0.29373(8) 0.19669(4) 0.77555(5) 0.01338(11) Uani 1 1 d . . . . .
C16 C 0.07380(8) 0.10553(4) 0.68771(6) 0.01622(12) Uani 1 1 d . . . . .
C17 C -0.03606(10) 0.10195(5) 0.56721(6) 0.02283(15) Uani 1 1 d . . . . .
H17A H -0.1183 0.0610 0.5616 0.034 Uiso 1 1 calc R U . . .
H17B H 0.0292 0.0897 0.5156 0.034 Uiso 1 1 calc R U . . .
H17C H -0.0898 0.1529 0.5468 0.034 Uiso 1 1 calc R U . . .
C18 C 0.16749(11) 0.02918(5) 0.71991(8) 0.02842(17) Uani 1 1 d . . . . .
H18A H 0.0909 -0.0142 0.7163 0.043 Uiso 1 1 calc R U . . .
H18B H 0.2397 0.0335 0.7969 0.043 Uiso 1 1 calc R U . . .
H18C H 0.2322 0.0190 0.6673 0.043 Uiso 1 1 calc R U . . .
C19 C -0.02618(10) 0.12605(6) 0.76802(7) 0.02925(19) Uani 1 1 d . . . . .
H19A H -0.1113 0.0864 0.7617 0.044 Uiso 1 1 calc R U . . .
H19B H -0.0763 0.1778 0.7484 0.044 Uiso 1 1 calc R U . . .
H19C H 0.0446 0.1271 0.8457 0.044 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.2217(8) . ?
O2 C15 1.3496(8) . ?
O2 C16 1.4720(8) . ?
N1 C15 1.3492(9) . ?
N1 C3 1.4557(8) . ?
N1 C10 1.4620(8) . ?
N2 C13 1.1508(10) . ?
N3 C14 1.1519(9) . ?
C1 C2 1.5361(11) . ?
C1 C10 1.5404(10) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.5401(10) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5472(9) . ?
C3 H3A 1.0000 . ?
C4 C11 1.5069(9) . ?
C4 C5 1.5420(9) . ?
C4 H4A 1.0000 . ?
C5 C6 1.5083(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.3357(10) . ?
C6 H6A 0.9500 . ?
C7 C8 1.5035(11) . ?
C7 H7A 0.9500 . ?
C8 C9 1.5447(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C11 1.5035(9) . ?
C9 C10 1.5447(10) . ?
C9 H9A 1.0000 . ?
C10 H10A 1.0000 . ?
C11 C12 1.3555(9) . ?
C12 C14 1.4386(10) . ?
C12 C13 1.4395(9) . ?
C16 C18 1.5201(11) . ?
C16 C19 1.5211(10) . ?
C16 C17 1.5215(10) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
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
C15 O2 C16 120.20(5) . . ?
C15 N1 C3 123.82(5) . . ?
C15 N1 C10 130.43(5) . . ?
C3 N1 C10 105.52(5) . . ?
C2 C1 C10 104.90(5) . . ?
C2 C1 H1A 110.8 . . ?
C10 C1 H1A 110.8 . . ?
C2 C1 H1B 110.8 . . ?
C10 C1 H1B 110.8 . . ?
H1A C1 H1B 108.8 . . ?
C1 C2 C3 104.68(6) . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
N1 C3 C2 101.97(5) . . ?
N1 C3 C4 108.33(5) . . ?
C2 C3 C4 111.25(5) . . ?
N1 C3 H3A 111.6 . . ?
C2 C3 H3A 111.6 . . ?
C4 C3 H3A 111.6 . . ?
C11 C4 C5 109.63(5) . . ?
C11 C4 C3 110.19(5) . . ?
C5 C4 C3 113.08(5) . . ?
C11 C4 H4A 107.9 . . ?
C5 C4 H4A 107.9 . . ?
C3 C4 H4A 107.9 . . ?
C6 C5 C4 120.31(5) . . ?
C6 C5 H5A 107.2 . . ?
C4 C5 H5A 107.2 . . ?
C6 C5 H5B 107.2 . . ?
C4 C5 H5B 107.2 . . ?
H5A C5 H5B 106.9 . . ?
C7 C6 C5 132.59(7) . . ?
C7 C6 H6A 113.7 . . ?
C5 C6 H6A 113.7 . . ?
C6 C7 C8 131.94(7) . . ?
C6 C7 H7A 114.0 . . ?
C8 C7 H7A 114.0 . . ?
C7 C8 C9 119.61(5) . . ?
C7 C8 H8A 107.4 . . ?
C9 C8 H8A 107.4 . . ?
C7 C8 H8B 107.4 . . ?
C9 C8 H8B 107.4 . . ?
H8A C8 H8B 107.0 . . ?
C11 C9 C8 109.88(5) . . ?
C11 C9 C10 110.32(5) . . ?
C8 C9 C10 113.09(6) . . ?
C11 C9 H9A 107.8 . . ?
C8 C9 H9A 107.8 . . ?
C10 C9 H9A 107.8 . . ?
N1 C10 C1 101.32(5) . . ?
N1 C10 C9 109.75(5) . . ?
C1 C10 C9 110.62(6) . . ?
N1 C10 H10A 111.6 . . ?
C1 C10 H10A 111.6 . . ?
C9 C10 H10A 111.6 . . ?
C12 C11 C9 121.24(6) . . ?
C12 C11 C4 121.10(6) . . ?
C9 C11 C4 117.50(5) . . ?
C11 C12 C14 121.58(6) . . ?
C11 C12 C13 122.27(6) . . ?
C14 C12 C13 116.01(6) . . ?
N2 C13 C12 178.30(9) . . ?
N3 C14 C12 177.41(8) . . ?
O1 C15 N1 123.35(6) . . ?
O1 C15 O2 125.59(6) . . ?
N1 C15 O2 111.06(5) . . ?
O2 C16 C18 109.39(6) . . ?
O2 C16 C19 111.85(6) . . ?
C18 C16 C19 112.24(7) . . ?
O2 C16 C17 102.18(5) . . ?
C18 C16 C17 110.98(7) . . ?
C19 C16 C17 109.77(6) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 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 . . ?

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
C10 C1 C2 C3 1.34(7) . . . . ?
C15 N1 C3 C2 139.97(7) . . . . ?
C10 N1 C3 C2 -45.06(6) . . . . ?
C15 N1 C3 C4 -102.61(7) . . . . ?
C10 N1 C3 C4 72.36(6) . . . . ?
C1 C2 C3 N1 25.47(7) . . . . ?
C1 C2 C3 C4 -89.83(6) . . . . ?
N1 C3 C4 C11 -55.96(7) . . . . ?
C2 C3 C4 C11 55.35(7) . . . . ?
N1 C3 C4 C5 67.12(6) . . . . ?
C2 C3 C4 C5 178.42(5) . . . . ?
C11 C4 C5 C6 48.59(8) . . . . ?
C3 C4 C5 C6 -74.79(8) . . . . ?
C4 C5 C6 C7 -23.52(12) . . . . ?
C5 C6 C7 C8 1.86(14) . . . . ?
C6 C7 C8 C9 21.99(12) . . . . ?
C7 C8 C9 C11 -50.57(8) . . . . ?
C7 C8 C9 C10 73.19(8) . . . . ?
C15 N1 C10 C1 -139.75(7) . . . . ?
C3 N1 C10 C1 45.74(6) . . . . ?
C15 N1 C10 C9 103.28(8) . . . . ?
C3 N1 C10 C9 -71.23(6) . . . . ?
C2 C1 C10 N1 -27.47(7) . . . . ?
C2 C1 C10 C9 88.86(7) . . . . ?
C11 C9 C10 N1 52.88(7) . . . . ?
C8 C9 C10 N1 -70.64(7) . . . . ?
C11 C9 C10 C1 -58.10(7) . . . . ?
C8 C9 C10 C1 178.39(5) . . . . ?
C8 C9 C11 C12 -88.48(8) . . . . ?
C10 C9 C11 C12 146.16(6) . . . . ?
C8 C9 C11 C4 87.01(7) . . . . ?
C10 C9 C11 C4 -38.35(8) . . . . ?
C5 C4 C11 C12 90.44(7) . . . . ?
C3 C4 C11 C12 -144.49(6) . . . . ?
C5 C4 C11 C9 -85.06(7) . . . . ?
C3 C4 C11 C9 40.01(8) . . . . ?
C9 C11 C12 C14 174.15(6) . . . . ?
C4 C11 C12 C14 -1.18(10) . . . . ?
C9 C11 C12 C13 -1.28(10) . . . . ?
C4 C11 C12 C13 -176.61(6) . . . . ?
C3 N1 C15 O1 -9.09(11) . . . . ?
C10 N1 C15 O1 177.29(7) . . . . ?
C3 N1 C15 O2 170.83(6) . . . . ?
C10 N1 C15 O2 -2.79(10) . . . . ?
C16 O2 C15 O1 -0.69(10) . . . . ?
C16 O2 C15 N1 179.39(6) . . . . ?
C15 O2 C16 C18 -70.38(8) . . . . ?
C15 O2 C16 C19 54.61(8) . . . . ?
C15 O2 C16 C17 171.96(6) . . . . ?

_refine_diff_density_max         0.526
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.052

