# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2103494'
loop_
_audit_author_name
_audit_author_address
'Sunder Dhuri Sarvesh Harmalkar'
;Goa University
India
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2021-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H32 N3 O'
_chemical_formula_weight         438.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3376(5)
_cell_length_b                   11.2041(6)
_cell_length_c                   11.6795(6)
_cell_angle_alpha                80.990(2)
_cell_angle_beta                 68.5320(10)
_cell_angle_gamma                81.497(2)
_cell_volume                     1237.33(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8924
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      28.25

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_F_000             470
_exptl_transmission_factor_min   0.7010
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24419
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.671
_diffrn_reflns_theta_max         28.255
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6117
_reflns_number_gt                4386
_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0704P)²+0.3741P] 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         6117
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1649
_refine_ls_wR_factor_gt          0.1460
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.80765(12) 0.21239(13) 0.72286(12) 0.0417(3) Uani 1 1 d . . . . .
C1 C 0.35925(16) 0.16334(18) 0.67066(16) 0.0497(4) Uani 1 1 d . . . . .
O1 O 0.22171(13) 0.17357(19) 0.68089(16) 0.0878(5) Uani 1 1 d . . . . .
C3 C 0.58510(16) 0.22848(15) 0.55716(14) 0.0421(3) Uani 1 1 d . . . . .
H3 H 0.644463 0.275027 0.491194 0.051 Uiso 1 1 calc R U . . .
N3 N 0.91168(15) 0.24492(17) 0.84136(15) 0.0595(4) Uani 1 1 d . . . . .
C2 C 0.44585(16) 0.23220(16) 0.56809(15) 0.0450(4) Uani 1 1 d . . . . .
N2 N 0.91373(14) 0.17087(16) 0.76345(15) 0.0565(4) Uani 1 1 d . . . . .
C4 C 0.63775(14) 0.15787(14) 0.64116(13) 0.0378(3) Uani 1 1 d . . . . .
C6 C 0.40907(16) 0.08697(17) 0.75545(14) 0.0462(4) Uani 1 1 d . . . . .
C5 C 0.54995(16) 0.08673(15) 0.73831(14) 0.0433(4) Uani 1 1 d . . . . .
H5 H 0.586015 0.037457 0.793626 0.052 Uiso 1 1 calc R U . . .
C7 C 0.3917(2) 0.30329(18) 0.46782(19) 0.0568(5) Uani 1 1 d . . . . .
C9 C 0.5062(3) 0.3687(2) 0.3649(2) 0.0789(7) Uani 1 1 d . . . . .
H9A H 0.583341 0.310795 0.328825 0.118 Uiso 1 1 calc R U . . .
H9B H 0.537134 0.427269 0.398522 0.118 Uiso 1 1 calc R U . . .
H9C H 0.470173 0.409350 0.302484 0.118 Uiso 1 1 calc R U . . .
C8 C 0.3414(3) 0.2136(2) 0.4095(2) 0.0745(6) Uani 1 1 d . . . . .
H8A H 0.315347 0.256117 0.341994 0.112 Uiso 1 1 calc R U . . .
H8B H 0.262136 0.177862 0.470775 0.112 Uiso 1 1 calc R U . . .
H8C H 0.415299 0.150978 0.379547 0.112 Uiso 1 1 calc R U . . .
C10 C 0.2716(3) 0.4007(2) 0.5219(3) 0.0869(8) Uani 1 1 d . . . . .
H10A H 0.303384 0.456002 0.558571 0.130 Uiso 1 1 calc R U . . .
H10B H 0.194796 0.362318 0.583883 0.130 Uiso 1 1 calc R U . . .
H10C H 0.241625 0.444515 0.457011 0.130 Uiso 1 1 calc R U . . .
C11 C 0.3149(2) 0.0037(2) 0.86138(17) 0.0587(5) Uani 1 1 d . . . . .
C12 C 0.2378(3) -0.0721(3) 0.8131(2) 0.0881(8) Uani 1 1 d . . . . .
H12A H 0.302753 -0.108229 0.741935 0.132 Uiso 1 1 calc R U . . .
H12B H 0.166108 -0.020644 0.790407 0.132 Uiso 1 1 calc R U . . .
H12C H 0.196366 -0.134809 0.876661 0.132 Uiso 1 1 calc R U . . .
C13 C 0.2096(3) 0.0780(3) 0.9606(2) 0.1008(10) Uani 1 1 d . . . . .
H13A H 0.152662 0.135206 0.924369 0.151 Uiso 1 1 calc R U . . .
H13B H 0.258524 0.120909 0.994508 0.151 Uiso 1 1 calc R U . . .
H13C H 0.151380 0.024728 1.025267 0.151 Uiso 1 1 calc R U . . .
C14 C 0.4015(3) -0.0891(3) 0.9217(2) 0.0878(8) Uani 1 1 d . . . . .
H14A H 0.470180 -0.134829 0.859825 0.132 Uiso 1 1 calc R U . . .
H14B H 0.341261 -0.143236 0.983532 0.132 Uiso 1 1 calc R U . . .
H14C H 0.447357 -0.047662 0.959707 0.132 Uiso 1 1 calc R U . . .
C15 C 0.79127(14) 0.15056(14) 0.62705(13) 0.0384(3) Uani 1 1 d . . . . .
H15 H 0.822124 0.064451 0.642120 0.046 Uiso 1 1 calc R U . . .
C16 C 0.88640(14) 0.19608(15) 0.49853(14) 0.0398(3) Uani 1 1 d . . . . .
C17 C 0.92750(18) 0.11951(18) 0.40674(16) 0.0526(4) Uani 1 1 d . . . . .
H17 H 0.900098 0.041255 0.425457 0.063 Uiso 1 1 calc R U . . .
C18 C 1.0094(2) 0.1591(2) 0.28700(17) 0.0633(5) Uani 1 1 d . . . . .
H18 H 1.037266 0.107025 0.225749 0.076 Uiso 1 1 calc R U . . .
C19 C 1.0496(2) 0.2748(2) 0.25828(17) 0.0637(5) Uani 1 1 d . . . . .
H19 H 1.102984 0.301655 0.177486 0.076 Uiso 1 1 calc R U . . .
C20 C 1.0106(2) 0.3502(2) 0.34909(19) 0.0638(5) Uani 1 1 d . . . . .
H20 H 1.038076 0.428496 0.329857 0.077 Uiso 1 1 calc R U . . .
C21 C 0.93064(18) 0.31103(17) 0.46939(17) 0.0521(4) Uani 1 1 d . . . . .
H21 H 0.906560 0.362337 0.530916 0.063 Uiso 1 1 calc R U . . .
C22 C 0.73724(16) 0.31225(15) 0.77495(14) 0.0435(4) Uani 1 1 d . . . . .
H22 H 0.659496 0.357250 0.762395 0.052 Uiso 1 1 calc R U . . .
C23 C 0.80415(16) 0.33405(16) 0.85075(14) 0.0453(4) Uani 1 1 d . . . . .
C24 C 0.77060(18) 0.42725(17) 0.93587(15) 0.0498(4) Uani 1 1 d . . . . .
C25 C 0.6731(2) 0.52507(19) 0.93339(18) 0.0601(5) Uani 1 1 d . . . . .
H25 H 0.630042 0.534073 0.874800 0.072 Uiso 1 1 calc R U . . .
C26 C 0.6383(3) 0.6103(2) 1.0169(2) 0.0728(6) Uani 1 1 d . . . . .
H26 H 0.572235 0.675670 1.014279 0.087 Uiso 1 1 calc R U . . .
C27 C 0.7016(3) 0.5977(2) 1.1033(2) 0.0805(7) Uani 1 1 d . . . . .
H27 H 0.677730 0.654066 1.160086 0.097 Uiso 1 1 calc R U . . .
C28 C 0.7998(3) 0.5023(3) 1.1060(2) 0.0843(7) Uani 1 1 d . . . . .
H28 H 0.843322 0.494814 1.164149 0.101 Uiso 1 1 calc R U . . .
C29 C 0.8352(2) 0.4166(2) 1.0232(2) 0.0695(6) Uani 1 1 d . . . . .
H29 H 0.902151 0.352016 1.025981 0.083 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
N1 C22 1.342(2) . ?
N1 N2 1.3432(19) . ?
N1 C15 1.4754(19) . ?
C1 O1 1.371(2) . ?
C1 C6 1.398(3) . ?
C1 C2 1.401(2) . ?
C3 C4 1.380(2) . ?
C3 C2 1.393(2) . ?
C3 H3 0.9300 . ?
N3 N2 1.317(2) . ?
N3 C23 1.364(2) . ?
C2 C7 1.541(2) . ?
C4 C5 1.387(2) . ?
C4 C15 1.525(2) . ?
C6 C5 1.395(2) . ?
C6 C11 1.541(2) . ?
C5 H5 0.9300 . ?
C7 C9 1.524(3) . ?
C7 C8 1.540(3) . ?
C7 C10 1.541(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C13 1.528(3) . ?
C11 C14 1.528(3) . ?
C11 C12 1.534(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.519(2) . ?
C15 H15 0.9800 . ?
C16 C21 1.381(2) . ?
C16 C17 1.383(2) . ?
C17 C18 1.385(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.367(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.374(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.471(2) . ?
C24 C25 1.379(3) . ?
C24 C29 1.392(3) . ?
C25 C26 1.388(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.370(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.365(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.385(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?

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
C22 N1 N2 110.87(13) . . ?
C22 N1 C15 130.59(13) . . ?
N2 N1 C15 118.41(13) . . ?
O1 C1 C6 121.94(16) . . ?
O1 C1 C2 115.24(16) . . ?
C6 C1 C2 122.80(14) . . ?
C4 C3 C2 122.06(15) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
N2 N3 C23 109.43(14) . . ?
C3 C2 C1 117.07(15) . . ?
C3 C2 C7 121.31(15) . . ?
C1 C2 C7 121.54(15) . . ?
N3 N2 N1 106.93(14) . . ?
C3 C4 C5 119.03(14) . . ?
C3 C4 C15 122.12(13) . . ?
C5 C4 C15 118.77(14) . . ?
C5 C6 C1 117.01(15) . . ?
C5 C6 C11 120.88(16) . . ?
C1 C6 C11 122.09(15) . . ?
C4 C5 C6 121.89(15) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C9 C7 C8 107.90(18) . . ?
C9 C7 C2 111.57(15) . . ?
C8 C7 C2 108.97(16) . . ?
C9 C7 C10 106.98(19) . . ?
C8 C7 C10 109.86(17) . . ?
C2 C7 C10 111.48(17) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C11 C14 108.6(2) . . ?
C13 C11 C12 109.8(2) . . ?
C14 C11 C12 105.1(2) . . ?
C13 C11 C6 110.70(18) . . ?
C14 C11 C6 111.10(16) . . ?
C12 C11 C6 111.34(16) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C16 111.18(12) . . ?
N1 C15 C4 110.71(11) . . ?
C16 C15 C4 114.17(12) . . ?
N1 C15 H15 106.8 . . ?
C16 C15 H15 106.8 . . ?
C4 C15 H15 106.8 . . ?
C21 C16 C17 118.99(15) . . ?
C21 C16 C15 122.77(14) . . ?
C17 C16 C15 118.22(15) . . ?
C16 C17 C18 120.18(18) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 120.33(18) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 119.67(17) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.47(19) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 120.32(17) . . ?
C16 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
N1 C22 C23 105.52(15) . . ?
N1 C22 H22 127.2 . . ?
C23 C22 H22 127.2 . . ?
N3 C23 C22 107.25(15) . . ?
N3 C23 C24 122.19(15) . . ?
C22 C23 C24 130.45(16) . . ?
C25 C24 C29 118.45(18) . . ?
C25 C24 C23 121.37(16) . . ?
C29 C24 C23 120.17(19) . . ?
C24 C25 C26 121.0(2) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C27 C26 C25 119.8(2) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C28 C27 C26 120.0(2) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 120.7(2) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C28 C29 C24 120.0(2) . . ?
C28 C29 H29 120.0 . . ?
C24 C29 H29 120.0 . . ?

_refine_diff_density_max         0.540
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2103495'
loop_
_audit_author_name
_audit_author_address
'Sunder Dhuri Sarvesh Harmalkar'
;Goa University
India
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2021-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H32 N3 O'
_chemical_formula_weight         438.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0143(14)
_cell_length_b                   15.747(2)
_cell_length_c                   15.541(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.578(4)
_cell_angle_gamma                90
_cell_volume                     2608.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5549
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      24.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_F_000             940
_exptl_transmission_factor_min   0.6880
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34744
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.587
_diffrn_reflns_theta_max         28.327
_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             6494
_reflns_number_gt                3196
_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0767P)²+0.5234P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0089(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6494
_refine_ls_number_parameters     305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1382
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1957
_refine_ls_wR_factor_gt          0.1487
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.53736(15) 0.40892(10) 0.39111(10) 0.0491(4) Uani 1 1 d . . . . .
C1 C 0.1439(2) 0.25059(16) 0.38802(16) 0.0653(6) Uani 1 1 d . . . . .
O1 O 0.02842(15) 0.21119(13) 0.36329(15) 0.1058(7) Uani 1 1 d . . . . .
N2 N 0.52033(17) 0.37006(11) 0.31312(12) 0.0615(5) Uani 1 1 d . . . . .
C2 C 0.2481(2) 0.19876(14) 0.42169(15) 0.0599(6) Uani 1 1 d . . . . .
C3 C 0.36427(19) 0.23871(13) 0.44650(14) 0.0559(5) Uani 1 1 d . . . . .
H3 H 0.435273 0.206012 0.469716 0.067 Uiso 1 1 calc R U . . .
N3 N 0.60160(16) 0.48154(10) 0.39817(11) 0.0535(4) Uani 1 1 d . . . . .
C4 C 0.37790(18) 0.32509(13) 0.43790(13) 0.0495(5) Uani 1 1 d . . . . .
C7 C 0.2354(2) 0.10233(16) 0.4317(2) 0.0822(8) Uani 1 1 d . . . . .
C6 C 0.15278(19) 0.33882(15) 0.37899(15) 0.0628(6) Uani 1 1 d . . . . .
C5 C 0.27199(19) 0.37370(14) 0.40448(14) 0.0577(5) Uani 1 1 d . . . . .
H5 H 0.281089 0.432009 0.398896 0.069 Uiso 1 1 calc R U . . .
C8 C 0.3632(3) 0.06082(17) 0.4704(3) 0.1278(14) Uani 1 1 d . . . . .
H8A H 0.351995 0.001190 0.478664 0.192 Uiso 1 1 calc R U . . .
H8B H 0.402177 0.086510 0.526564 0.192 Uiso 1 1 calc R U . . .
H8C H 0.415637 0.068739 0.430139 0.192 Uiso 1 1 calc R U . . .
C9 C 0.1512(4) 0.0820(2) 0.4942(3) 0.1348(14) Uani 1 1 d . . . . .
H9A H 0.070263 0.107555 0.471573 0.202 Uiso 1 1 calc R U . . .
H9B H 0.188753 0.104181 0.552365 0.202 Uiso 1 1 calc R U . . .
H9C H 0.141808 0.021594 0.497774 0.202 Uiso 1 1 calc R U . . .
C10 C 0.1816(3) 0.06215(19) 0.3399(2) 0.1250(13) Uani 1 1 d . . . . .
H10A H 0.099402 0.084730 0.314439 0.188 Uiso 1 1 calc R U . . .
H10B H 0.176196 0.001708 0.346145 0.188 Uiso 1 1 calc R U . . .
H10C H 0.235462 0.074903 0.301741 0.188 Uiso 1 1 calc R U . . .
C11 C 0.0373(2) 0.39680(19) 0.3448(2) 0.0875(8) Uani 1 1 d . . . . .
C12 C 0.0754(3) 0.4902(2) 0.3465(3) 0.1292(14) Uani 1 1 d . . . . .
H12A H 0.129022 0.498645 0.307198 0.194 Uiso 1 1 calc R U . . .
H12B H 0.119395 0.505794 0.405879 0.194 Uiso 1 1 calc R U . . .
H12C H 0.001712 0.524736 0.327514 0.194 Uiso 1 1 calc R U . . .
C13 C -0.0301(3) 0.3744(3) 0.2488(3) 0.1426(15) Uani 1 1 d . . . . .
H13A H -0.100338 0.411696 0.228366 0.214 Uiso 1 1 calc R U . . .
H13B H -0.059076 0.316703 0.246206 0.214 Uiso 1 1 calc R U . . .
H13C H 0.026954 0.380622 0.211565 0.214 Uiso 1 1 calc R U . . .
C14 C -0.0514(3) 0.3890(3) 0.4065(3) 0.1364(14) Uani 1 1 d . . . . .
H14A H -0.119250 0.428628 0.388204 0.205 Uiso 1 1 calc R U . . .
H14B H -0.006052 0.401258 0.466518 0.205 Uiso 1 1 calc R U . . .
H14C H -0.084260 0.332335 0.403364 0.205 Uiso 1 1 calc R U . . .
C15 C 0.50344(18) 0.37059(13) 0.46816(13) 0.0510(5) Uani 1 1 d . . . . .
H15 H 0.490352 0.417772 0.505951 0.061 Uiso 1 1 calc R U . . .
C16 C 0.61014(19) 0.31848(13) 0.52329(13) 0.0534(5) Uani 1 1 d . . . . .
C17 C 0.6934(3) 0.2762(2) 0.48774(18) 0.0904(9) Uani 1 1 d . . . . .
H17 H 0.686610 0.280289 0.427012 0.108 Uiso 1 1 calc R U . . .
C18 C 0.7884(3) 0.2270(2) 0.5400(2) 0.1168(12) Uani 1 1 d . . . . .
H18 H 0.843916 0.197940 0.514337 0.140 Uiso 1 1 calc R U . . .
C19 C 0.7998(3) 0.2217(2) 0.6293(2) 0.1070(11) Uani 1 1 d . . . . .
H19 H 0.863568 0.189369 0.664988 0.128 Uiso 1 1 calc R U . . .
C20 C 0.7183(4) 0.2635(3) 0.6653(2) 0.1181(12) Uani 1 1 d . . . . .
H20 H 0.725974 0.259806 0.726151 0.142 Uiso 1 1 calc R U . . .
C21 C 0.6234(3) 0.3120(2) 0.61310(17) 0.0983(10) Uani 1 1 d . . . . .
H21 H 0.567949 0.340562 0.639182 0.118 Uiso 1 1 calc R U . . .
C22 C 0.5759(2) 0.42195(14) 0.26713(15) 0.0623(6) Uani 1 1 d . . . . .
H22 H 0.580182 0.412994 0.208813 0.075 Uiso 1 1 calc R U . . .
C23 C 0.62622(18) 0.49101(13) 0.31865(13) 0.0508(5) Uani 1 1 d . . . . .
C24 C 0.6990(2) 0.56272(13) 0.29797(15) 0.0573(5) Uani 1 1 d . . . . .
C25 C 0.7244(3) 0.56797(17) 0.21534(17) 0.0777(7) Uani 1 1 d . . . . .
H25 H 0.689776 0.528200 0.171837 0.093 Uiso 1 1 calc R U . . .
C26 C 0.7998(3) 0.6309(2) 0.1967(2) 0.1003(10) Uani 1 1 d . . . . .
H26 H 0.816850 0.633053 0.141049 0.120 Uiso 1 1 calc R U . . .
C27 C 0.8501(3) 0.6903(2) 0.2593(3) 0.1067(11) Uani 1 1 d . . . . .
H27 H 0.901963 0.732602 0.246641 0.128 Uiso 1 1 calc R U . . .
C28 C 0.8240(3) 0.68768(19) 0.3406(2) 0.1071(11) Uani 1 1 d . . . . .
H28 H 0.856428 0.728990 0.382902 0.129 Uiso 1 1 calc R U . . .
C29 C 0.7492(3) 0.62349(16) 0.36004(19) 0.0822(8) Uani 1 1 d . . . . .
H29 H 0.732842 0.621517 0.415864 0.099 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
N1 N2 1.328(2) . ?
N1 N3 1.335(2) . ?
N1 C15 1.471(2) . ?
C1 O1 1.380(3) . ?
C1 C2 1.398(3) . ?
C1 C6 1.402(3) . ?
N2 C22 1.332(3) . ?
C2 C3 1.391(3) . ?
C2 C7 1.536(3) . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
N3 C23 1.338(2) . ?
C4 C5 1.383(3) . ?
C4 C15 1.523(3) . ?
C7 C8 1.531(4) . ?
C7 C9 1.536(4) . ?
C7 C10 1.537(4) . ?
C6 C5 1.386(3) . ?
C6 C11 1.547(3) . ?
C5 H5 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.527(4) . ?
C11 C13 1.532(4) . ?
C11 C14 1.536(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.511(3) . ?
C15 H15 0.9800 . ?
C16 C17 1.358(3) . ?
C16 C21 1.370(3) . ?
C17 C18 1.388(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.344(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.381(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.467(3) . ?
C24 C29 1.372(3) . ?
C24 C25 1.384(3) . ?
C25 C26 1.370(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.363(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.365(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.384(4) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?

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
N2 N1 N3 114.84(16) . . ?
N2 N1 C15 123.18(16) . . ?
N3 N1 C15 121.52(15) . . ?
O1 C1 C2 117.0(2) . . ?
O1 C1 C6 120.0(2) . . ?
C2 C1 C6 123.0(2) . . ?
N1 N2 C22 103.21(17) . . ?
C3 C2 C1 116.8(2) . . ?
C3 C2 C7 121.3(2) . . ?
C1 C2 C7 121.9(2) . . ?
C4 C3 C2 122.32(19) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
N1 N3 C23 104.24(16) . . ?
C3 C4 C5 118.72(19) . . ?
C3 C4 C15 123.16(18) . . ?
C5 C4 C15 118.04(18) . . ?
C8 C7 C9 107.8(3) . . ?
C8 C7 C2 111.3(2) . . ?
C9 C7 C2 110.8(2) . . ?
C8 C7 C10 106.9(3) . . ?
C9 C7 C10 110.4(3) . . ?
C2 C7 C10 109.7(2) . . ?
C5 C6 C1 116.67(19) . . ?
C5 C6 C11 120.1(2) . . ?
C1 C6 C11 123.2(2) . . ?
C4 C5 C6 122.5(2) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C13 107.6(3) . . ?
C12 C11 C14 106.3(3) . . ?
C13 C11 C14 111.2(3) . . ?
C12 C11 C6 111.3(2) . . ?
C13 C11 C6 110.7(3) . . ?
C14 C11 C6 109.6(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C16 111.35(16) . . ?
N1 C15 C4 109.80(15) . . ?
C16 C15 C4 115.84(17) . . ?
N1 C15 H15 106.4 . . ?
C16 C15 H15 106.4 . . ?
C4 C15 H15 106.4 . . ?
C17 C16 C21 117.9(2) . . ?
C17 C16 C15 123.0(2) . . ?
C21 C16 C15 119.1(2) . . ?
C16 C17 C18 121.5(3) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 119.5(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C20 C19 C18 119.6(3) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.8(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C16 C21 C20 120.7(3) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
N2 C22 C23 110.09(19) . . ?
N2 C22 H22 125.0 . . ?
C23 C22 H22 125.0 . . ?
N3 C23 C22 107.61(18) . . ?
N3 C23 C24 122.48(18) . . ?
C22 C23 C24 129.9(2) . . ?
C29 C24 C25 118.1(2) . . ?
C29 C24 C23 121.9(2) . . ?
C25 C24 C23 119.9(2) . . ?
C26 C25 C24 121.0(3) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C27 C26 C25 120.3(3) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C28 119.8(3) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C27 C28 C29 120.0(3) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C24 C29 C28 120.8(3) . . ?
C24 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033

