# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2025

####################################################################### 
# 
# 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_UMD2943G_A
_database_code_depnum_ccdc_archive 'CCDC 2450970'
loop_
_audit_author_name
_audit_author_address
'James A. Golen'
;UMass Dartmouth
United States of America
;
_audit_update_record             
;
2025-05-13 deposited with the CCDC.	2025-10-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 N3 O'
_chemical_formula_weight         255.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   5.9147(4)
_cell_length_b                   9.7728(7)
_cell_length_c                   11.5476(7)
_cell_angle_alpha                97.578(2)
_cell_angle_beta                 94.638(2)
_cell_angle_gamma                90.006(2)
_cell_volume                     659.45(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    8820
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      26.38

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-IV photon 200'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20148
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.933
_diffrn_reflns_theta_max         26.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2725
_reflns_number_gt                2328
_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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0517P)²+0.1374P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   'Fourier difference maps'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.021(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2725
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2090(2) 0.05884(11) 0.33514(11) 0.0685(3) Uani 1 1 d . . . . .
N1 N 0.3726(2) 0.37902(13) 0.12417(10) 0.0474(3) Uani 1 1 d . . . . .
N2 N 0.46745(18) 0.23556(10) 0.38622(9) 0.0405(3) Uani 1 1 d . . . . .
N3 N 0.67789(17) 0.43857(10) 0.38512(9) 0.0373(2) Uani 1 1 d . . . . .
C1 C 0.2062(2) 0.26613(15) 0.12624(12) 0.0474(3) Uani 1 1 d . . . . .
C2 C 0.1553(2) 0.27983(14) 0.25917(12) 0.0448(3) Uani 1 1 d . . . . .
H2 H -0.0083 0.2820 0.2675 0.054 Uiso 1 1 calc R U . . .
C3 C 0.2705(2) 0.17553(14) 0.32901(12) 0.0466(3) Uani 1 1 d . . . . .
C4 C 0.4921(2) 0.37036(12) 0.36551(10) 0.0351(3) Uani 1 1 d . . . . .
C5 C 0.6731(2) 0.56723(12) 0.33966(10) 0.0367(3) Uani 1 1 d . . . . .
C6 C 0.8427(2) 0.66395(13) 0.38121(12) 0.0427(3) Uani 1 1 d . . . . .
H6 H 0.9508 0.6452 0.4399 0.051 Uiso 1 1 calc R U . . .
C7 C 0.8522(3) 0.78804(14) 0.33602(13) 0.0513(3) Uani 1 1 d . . . . .
H7 H 0.9666 0.8520 0.3641 0.062 Uiso 1 1 calc R U . . .
C8 C 0.6917(3) 0.81651(15) 0.24938(14) 0.0589(4) Uani 1 1 d . . . . .
H8 H 0.6983 0.8996 0.2186 0.071 Uiso 1 1 calc R U . . .
C9 C 0.5210(3) 0.72176(15) 0.20812(13) 0.0541(4) Uani 1 1 d . . . . .
H9 H 0.4123 0.7425 0.1504 0.065 Uiso 1 1 calc R U . . .
C10 C 0.5089(2) 0.59629(13) 0.25126(11) 0.0415(3) Uani 1 1 d . . . . .
C11 C 0.3171(2) 0.49461(13) 0.21227(11) 0.0420(3) Uani 1 1 d . . . . .
H11 H 0.1810 0.5421 0.1850 0.050 Uiso 1 1 calc R U . . .
C12 C 0.2688(2) 0.41603(13) 0.31218(11) 0.0387(3) Uani 1 1 d . . . . .
H12 H 0.1792 0.4693 0.3698 0.046 Uiso 1 1 calc R U . . .
C13 C -0.0130(3) 0.2873(2) 0.05081(16) 0.0747(5) Uani 1 1 d . . . . .
H13A H -0.1183 0.2138 0.0553 0.112 Uiso 1 1 calc R U . . .
H13B H 0.0205 0.2875 -0.0291 0.112 Uiso 1 1 calc R U . . .
H13C H -0.0786 0.3740 0.0790 0.112 Uiso 1 1 calc R U . . .
C14 C 0.3128(3) 0.12932(17) 0.08193(15) 0.0670(5) Uani 1 1 d . . . . .
H14A H 0.2102 0.0550 0.0880 0.100 Uiso 1 1 calc R U . . .
H14B H 0.4519 0.1179 0.1284 0.100 Uiso 1 1 calc R U . . .
H14C H 0.3436 0.1288 0.0015 0.100 Uiso 1 1 calc R U . . .
C15 C 0.6348(3) 0.16256(14) 0.45302(14) 0.0521(4) Uani 1 1 d . . . . .
H15A H 0.7827 0.1777 0.4280 0.078 Uiso 1 1 calc R U . . .
H15B H 0.5996 0.0656 0.4403 0.078 Uiso 1 1 calc R U . . .
H15C H 0.6329 0.1962 0.5349 0.078 Uiso 1 1 calc R U . . .
H1 H 0.377(4) 0.399(2) 0.053(2) 0.097(7) Uiso 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
O1 C3 1.2097(17) . ?
N1 C11 1.4730(17) . ?
N1 C1 1.4822(18) . ?
N1 H1 0.87(2) . ?
N2 C4 1.3794(15) . ?
N2 C3 1.3822(17) . ?
N2 C15 1.4512(17) . ?
N3 C4 1.2741(15) . ?
N3 C5 1.4245(15) . ?
C1 C14 1.523(2) . ?
C1 C13 1.532(2) . ?
C1 C2 1.5766(19) . ?
C2 C3 1.511(2) . ?
C2 C12 1.5215(18) . ?
C2 H2 0.9800 . ?
C4 C12 1.5047(17) . ?
C5 C6 1.3898(17) . ?
C5 C10 1.4080(17) . ?
C6 C7 1.3849(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.3869(18) . ?
C9 H9 0.9300 . ?
C10 C11 1.5088(18) . ?
C11 C12 1.5131(17) . ?
C11 H11 0.9800 . ?
C12 H12 0.9800 . ?
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 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
C11 N1 C1 107.95(10) . . ?
C11 N1 H1 115.5(15) . . ?
C1 N1 H1 110.1(14) . . ?
C4 N2 C3 111.63(11) . . ?
C4 N2 C15 124.26(11) . . ?
C3 N2 C15 123.99(11) . . ?
C4 N3 C5 114.20(10) . . ?
N1 C1 C14 108.87(12) . . ?
N1 C1 C13 111.49(13) . . ?
C14 C1 C13 110.01(13) . . ?
N1 C1 C2 103.13(10) . . ?
C14 C1 C2 113.71(12) . . ?
C13 C1 C2 109.48(12) . . ?
C3 C2 C12 103.65(10) . . ?
C3 C2 C1 115.44(11) . . ?
C12 C2 C1 103.68(10) . . ?
C3 C2 H2 111.2 . . ?
C12 C2 H2 111.2 . . ?
C1 C2 H2 111.2 . . ?
O1 C3 N2 124.19(14) . . ?
O1 C3 C2 127.88(13) . . ?
N2 C3 C2 107.93(11) . . ?
N3 C4 N2 124.05(11) . . ?
N3 C4 C12 127.76(11) . . ?
N2 C4 C12 108.13(10) . . ?
C6 C5 C10 119.57(11) . . ?
C6 C5 N3 118.28(11) . . ?
C10 C5 N3 122.09(11) . . ?
C7 C6 C5 120.63(13) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C6 119.85(13) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 120.07(13) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 121.17(13) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C5 118.70(12) . . ?
C9 C10 C11 122.06(12) . . ?
C5 C10 C11 119.11(11) . . ?
N1 C11 C10 114.63(10) . . ?
N1 C11 C12 99.96(10) . . ?
C10 C11 C12 109.69(10) . . ?
N1 C11 H11 110.7 . . ?
C10 C11 H11 110.7 . . ?
C12 C11 H11 110.7 . . ?
C4 C12 C11 107.82(10) . . ?
C4 C12 C2 102.57(10) . . ?
C11 C12 C2 107.62(10) . . ?
C4 C12 H12 112.7 . . ?
C11 C12 H12 112.7 . . ?
C2 C12 H12 112.7 . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C11 N1 C1 C14 -154.61(12) . . . . ?
C11 N1 C1 C13 83.85(15) . . . . ?
C11 N1 C1 C2 -33.53(13) . . . . ?
N1 C1 C2 C3 -102.85(13) . . . . ?
C14 C1 C2 C3 14.87(17) . . . . ?
C13 C1 C2 C3 138.36(13) . . . . ?
N1 C1 C2 C12 9.78(13) . . . . ?
C14 C1 C2 C12 127.50(13) . . . . ?
C13 C1 C2 C12 -109.01(13) . . . . ?
C4 N2 C3 O1 -178.62(13) . . . . ?
C15 N2 C3 O1 5.4(2) . . . . ?
C4 N2 C3 C2 2.17(14) . . . . ?
C15 N2 C3 C2 -173.84(12) . . . . ?
C12 C2 C3 O1 164.16(14) . . . . ?
C1 C2 C3 O1 -83.20(18) . . . . ?
C12 C2 C3 N2 -16.67(13) . . . . ?
C1 C2 C3 N2 95.98(13) . . . . ?
C5 N3 C4 N2 170.25(10) . . . . ?
C5 N3 C4 C12 -6.63(17) . . . . ?
C3 N2 C4 N3 -163.65(11) . . . . ?
C15 N2 C4 N3 12.34(19) . . . . ?
C3 N2 C4 C12 13.76(13) . . . . ?
C15 N2 C4 C12 -170.25(12) . . . . ?
C4 N3 C5 C6 163.71(11) . . . . ?
C4 N3 C5 C10 -19.02(16) . . . . ?
C10 C5 C6 C7 -0.38(19) . . . . ?
N3 C5 C6 C7 176.95(12) . . . . ?
C5 C6 C7 C8 0.3(2) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C7 C8 C9 C10 -0.9(2) . . . . ?
C8 C9 C10 C5 0.8(2) . . . . ?
C8 C9 C10 C11 176.63(13) . . . . ?
C6 C5 C10 C9 -0.16(19) . . . . ?
N3 C5 C10 C9 -177.39(12) . . . . ?
C6 C5 C10 C11 -176.12(11) . . . . ?
N3 C5 C10 C11 6.65(17) . . . . ?
C1 N1 C11 C10 160.12(11) . . . . ?
C1 N1 C11 C12 42.94(13) . . . . ?
C9 C10 C11 N1 100.75(15) . . . . ?
C5 C10 C11 N1 -83.43(14) . . . . ?
C9 C10 C11 C12 -147.78(13) . . . . ?
C5 C10 C11 C12 28.04(15) . . . . ?
N3 C4 C12 C11 40.59(16) . . . . ?
N2 C4 C12 C11 -136.70(10) . . . . ?
N3 C4 C12 C2 154.00(12) . . . . ?
N2 C4 C12 C2 -23.28(12) . . . . ?
N1 C11 C12 C4 74.58(11) . . . . ?
C10 C11 C12 C4 -46.24(13) . . . . ?
N1 C11 C12 C2 -35.42(12) . . . . ?
C10 C11 C12 C2 -156.23(10) . . . . ?
C3 C2 C12 C4 23.37(12) . . . . ?
C1 C2 C12 C4 -97.57(11) . . . . ?
C3 C2 C12 C11 136.94(10) . . . . ?
C1 C2 C12 C11 16.00(13) . . . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.030

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_umd2946d_a
_database_code_depnum_ccdc_archive 'CCDC 2450974'
loop_
_audit_author_name
_audit_author_address
'James A. Golen'
;UMass Dartmouth
United States of America
;
_audit_update_record             
;
2025-05-13 deposited with the CCDC.	2025-10-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H23 N5 O2'
_chemical_formula_weight         341.41

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                   13.4245(9)
_cell_length_b                   10.2009(9)
_cell_length_c                   13.9121(11)
_cell_angle_alpha                90
_cell_angle_beta                 107.050(3)
_cell_angle_gamma                90
_cell_volume                     1821.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      26.34

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.670
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-IV photon 200'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26709
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.516
_diffrn_reflns_theta_max         26.404
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3718
_reflns_number_gt                3037
_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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0574P)²+0.5638P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   'Fourier difference maps'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0059(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3718
_refine_ls_number_parameters     267
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.88868(9) 0.33520(12) 0.97915(8) 0.0668(3) Uani 1 1 d . . . . .
O2 O 0.58807(8) 0.40464(13) 0.73448(9) 0.0698(4) Uani 1 1 d . . . . .
N1 N 0.85635(10) 0.22146(13) 0.70300(9) 0.0508(3) Uani 1 1 d . . . . .
N2 N 0.75274(9) 0.41342(12) 0.84845(8) 0.0456(3) Uani 1 1 d . . . . .
N3 N 0.55619(11) 0.18238(15) 0.50443(11) 0.0652(4) Uani 1 1 d . . . . .
N4 N 0.48039(11) 0.15997(16) 0.43041(11) 0.0675(4) Uani 1 1 d . . . . .
N5 N 0.41081(14) 0.1264(2) 0.36816(14) 0.0988(7) Uani 1 1 d . . . . .
C1 C 0.88576(12) 0.14458(15) 0.79634(11) 0.0512(4) Uani 1 1 d . . . . .
C2 C 0.80014(11) 0.19011(14) 0.84318(10) 0.0450(3) Uani 1 1 d . . . . .
H2A H 0.7849 0.1212 0.8859 0.054 Uiso 1 1 calc R U . . .
C3 C 0.82256(11) 0.31833(14) 0.89953(10) 0.0461(3) Uani 1 1 d . . . . .
C4 C 0.67119(10) 0.35508(15) 0.77454(10) 0.0459(3) Uani 1 1 d . . . . .
C5 C 0.70411(11) 0.21914(14) 0.75437(10) 0.0437(3) Uani 1 1 d . . . . .
H5A H 0.6486 0.1551 0.7502 0.052 Uiso 1 1 calc R U . . .
C6 C 0.74363(11) 0.21328(14) 0.65917(10) 0.0451(3) Uani 1 1 d . . . . .
H6A H 0.7260 0.1275 0.6269 0.054 Uiso 1 1 calc R U . . .
C7 C 0.70294(11) 0.31938(14) 0.58173(10) 0.0442(3) Uani 1 1 d . . . . .
C8 C 0.60963(11) 0.30393(15) 0.50521(10) 0.0465(3) Uani 1 1 d . . . . .
C9 C 0.57088(11) 0.40322(16) 0.43590(11) 0.0535(4) Uani 1 1 d . . . . .
H9A H 0.5084 0.3914 0.3855 0.064 Uiso 1 1 calc R U . . .
C10 C 0.62506(13) 0.51903(17) 0.44185(12) 0.0589(4) Uani 1 1 d . . . . .
H10A H 0.5991 0.5858 0.3958 0.071 Uiso 1 1 calc R U . . .
C11 C 0.71753(14) 0.53542(16) 0.51602(13) 0.0613(4) Uani 1 1 d . . . . .
H11A H 0.7545 0.6133 0.5199 0.074 Uiso 1 1 calc R U . . .
C12 C 0.75610(13) 0.43635(15) 0.58523(11) 0.0542(4) Uani 1 1 d . . . . .
H12A H 0.8190 0.4488 0.6350 0.065 Uiso 1 1 calc R U . . .
C13 C 0.99707(13) 0.1790(2) 0.85649(14) 0.0723(5) Uani 1 1 d . . . . .
H13A H 1.0133 0.1383 0.9215 0.108 Uiso 1 1 calc R U . . .
H13B H 1.0036 0.2724 0.8644 0.108 Uiso 1 1 calc R U . . .
H13C H 1.0444 0.1480 0.8215 0.108 Uiso 1 1 calc R U . . .
C14 C 0.87581(17) -0.00430(18) 0.77907(15) 0.0779(6) Uani 1 1 d . . . . .
H14A H 0.8961 -0.0487 0.8427 0.117 Uiso 1 1 calc R U . . .
H14B H 0.9203 -0.0314 0.7398 0.117 Uiso 1 1 calc R U . . .
H14C H 0.8049 -0.0258 0.7438 0.117 Uiso 1 1 calc R U . . .
C15 C 0.75968(13) 0.55555(15) 0.87858(11) 0.0565(4) Uani 1 1 d D . . . .
C16 C 0.7451(4) 0.5683(3) 0.9810(2) 0.1032(14) Uani 0.792(5) 1 d D U P A 1
H16A H 0.7488 0.6591 0.9998 0.155 Uiso 0.792(5) 1 calc R U P A 1
H16B H 0.7989 0.5204 1.0288 0.155 Uiso 0.792(5) 1 calc R U P A 1
H16C H 0.6783 0.5336 0.9798 0.155 Uiso 0.792(5) 1 calc R U P A 1
C17 C 0.8707(2) 0.6007(3) 0.8823(3) 0.0947(11) Uani 0.792(5) 1 d D U P A 1
H17A H 0.8794 0.6913 0.9016 0.142 Uiso 0.792(5) 1 calc R U P A 1
H17B H 0.8806 0.5900 0.8172 0.142 Uiso 0.792(5) 1 calc R U P A 1
H17C H 0.9210 0.5488 0.9306 0.142 Uiso 0.792(5) 1 calc R U P A 1
C18 C 0.6857(3) 0.6395(3) 0.8014(3) 0.0981(12) Uani 0.792(5) 1 d D U P A 1
H18A H 0.7035 0.7301 0.8151 0.147 Uiso 0.792(5) 1 calc R U P A 1
H18B H 0.6158 0.6247 0.8038 0.147 Uiso 0.792(5) 1 calc R U P A 1
H18C H 0.6903 0.6174 0.7357 0.147 Uiso 0.792(5) 1 calc R U P A 1
C16A C 0.6582(9) 0.5814(11) 0.9139(10) 0.091(4) Uani 0.208(5) 1 d D U P A 2
H16D H 0.6631 0.6663 0.9447 0.136 Uiso 0.208(5) 1 calc R U P A 2
H16E H 0.6534 0.5155 0.9616 0.136 Uiso 0.208(5) 1 calc R U P A 2
H16F H 0.5974 0.5779 0.8566 0.136 Uiso 0.208(5) 1 calc R U P A 2
C17A C 0.8507(9) 0.5958(13) 0.9609(10) 0.114(5) Uani 0.208(5) 1 d D U P A 2
H17D H 0.8433 0.6859 0.9774 0.171 Uiso 0.208(5) 1 calc R U P A 2
H17E H 0.9126 0.5856 0.9404 0.171 Uiso 0.208(5) 1 calc R U P A 2
H17F H 0.8557 0.5421 1.0188 0.171 Uiso 0.208(5) 1 calc R U P A 2
C18A C 0.7460(11) 0.6368(12) 0.7851(8) 0.087(4) Uani 0.208(5) 1 d D U P A 2
H18D H 0.7376 0.7273 0.8001 0.130 Uiso 0.208(5) 1 calc R U P A 2
H18E H 0.6854 0.6075 0.7337 0.130 Uiso 0.208(5) 1 calc R U P A 2
H18F H 0.8064 0.6274 0.7620 0.130 Uiso 0.208(5) 1 calc R U P A 2
H1 H 0.8887(15) 0.195(2) 0.6615(15) 0.078(6) Uiso 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
O1 C3 1.2115(17) . ?
O2 C4 1.2027(17) . ?
N1 C6 1.4586(18) . ?
N1 C1 1.4685(19) . ?
N1 H1 0.86(2) . ?
N2 C3 1.3907(18) . ?
N2 C4 1.3964(17) . ?
N2 C15 1.5045(19) . ?
N3 N4 1.2384(19) . ?
N3 C8 1.431(2) . ?
N4 N5 1.125(2) . ?
C1 C13 1.524(2) . ?
C1 C14 1.537(2) . ?
C1 C2 1.549(2) . ?
C2 C3 1.509(2) . ?
C2 C5 1.5304(18) . ?
C2 H2A 0.9800 . ?
C4 C5 1.507(2) . ?
C5 C6 1.5656(19) . ?
C5 H5A 0.9800 . ?
C6 C7 1.5117(19) . ?
C6 H6A 0.9800 . ?
C7 C12 1.384(2) . ?
C7 C8 1.3948(19) . ?
C8 C9 1.390(2) . ?
C9 C10 1.377(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.372(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.387(2) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
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 C17A 1.467(9) . ?
C15 C16 1.499(3) . ?
C15 C18 1.500(3) . ?
C15 C18A 1.507(9) . ?
C15 C17 1.546(3) . ?
C15 C16A 1.599(8) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?
C17A H17D 0.9600 . ?
C17A H17E 0.9600 . ?
C17A H17F 0.9600 . ?
C18A H18D 0.9600 . ?
C18A H18E 0.9600 . ?
C18A H18F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C1 108.43(12) . . ?
C6 N1 H1 111.5(13) . . ?
C1 N1 H1 111.7(14) . . ?
C3 N2 C4 110.15(12) . . ?
C3 N2 C15 123.53(12) . . ?
C4 N2 C15 125.94(12) . . ?
N4 N3 C8 117.02(13) . . ?
N5 N4 N3 172.21(18) . . ?
N1 C1 C13 109.18(14) . . ?
N1 C1 C14 113.63(13) . . ?
C13 C1 C14 109.86(14) . . ?
N1 C1 C2 99.88(11) . . ?
C13 C1 C2 115.39(13) . . ?
C14 C1 C2 108.71(14) . . ?
C3 C2 C5 104.13(11) . . ?
C3 C2 C1 114.75(12) . . ?
C5 C2 C1 105.76(11) . . ?
C3 C2 H2A 110.6 . . ?
C5 C2 H2A 110.6 . . ?
C1 C2 H2A 110.6 . . ?
O1 C3 N2 124.85(14) . . ?
O1 C3 C2 125.39(13) . . ?
N2 C3 C2 109.71(11) . . ?
O2 C4 N2 125.63(14) . . ?
O2 C4 C5 125.70(13) . . ?
N2 C4 C5 108.66(11) . . ?
C4 C5 C2 104.56(11) . . ?
C4 C5 C6 112.54(11) . . ?
C2 C5 C6 105.15(11) . . ?
C4 C5 H5A 111.4 . . ?
C2 C5 H5A 111.4 . . ?
C6 C5 H5A 111.4 . . ?
N1 C6 C7 111.76(12) . . ?
N1 C6 C5 102.21(10) . . ?
C7 C6 C5 115.74(11) . . ?
N1 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C12 C7 C8 117.57(13) . . ?
C12 C7 C6 121.16(13) . . ?
C8 C7 C6 121.27(13) . . ?
C9 C8 C7 121.12(14) . . ?
C9 C8 N3 122.77(13) . . ?
C7 C8 N3 116.09(12) . . ?
C10 C9 C8 119.99(14) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C11 C10 C9 119.68(14) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
C10 C11 C12 120.30(16) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C7 C12 C11 121.34(15) . . ?
C7 C12 H12A 119.3 . . ?
C11 C12 H12A 119.3 . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C18 112.8(2) . . ?
C17A C15 N2 117.2(5) . . ?
C16 C15 N2 109.50(15) . . ?
C18 C15 N2 112.14(17) . . ?
C17A C15 C18A 112.5(7) . . ?
N2 C15 C18A 107.9(5) . . ?
C16 C15 C17 109.6(2) . . ?
C18 C15 C17 106.5(2) . . ?
N2 C15 C17 106.06(16) . . ?
C17A C15 C16A 107.7(6) . . ?
N2 C15 C16A 104.8(4) . . ?
C18A C15 C16A 106.0(6) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C16A H16D 109.5 . . ?
C15 C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
C15 C16A H16F 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C15 C17A H17D 109.5 . . ?
C15 C17A H17E 109.5 . . ?
H17D C17A H17E 109.5 . . ?
C15 C17A H17F 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C15 C18A H18D 109.5 . . ?
C15 C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
C15 C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C1 C13 -165.82(13) . . . . ?
C6 N1 C1 C14 71.17(17) . . . . ?
C6 N1 C1 C2 -44.40(14) . . . . ?
N1 C1 C2 C3 -82.65(14) . . . . ?
C13 C1 C2 C3 34.21(18) . . . . ?
C14 C1 C2 C3 158.10(13) . . . . ?
N1 C1 C2 C5 31.52(14) . . . . ?
C13 C1 C2 C5 148.38(14) . . . . ?
C14 C1 C2 C5 -87.73(14) . . . . ?
C4 N2 C3 O1 -164.66(14) . . . . ?
C15 N2 C3 O1 8.7(2) . . . . ?
C4 N2 C3 C2 12.78(15) . . . . ?
C15 N2 C3 C2 -173.88(12) . . . . ?
C5 C2 C3 O1 174.64(14) . . . . ?
C1 C2 C3 O1 -70.24(19) . . . . ?
C5 C2 C3 N2 -2.78(15) . . . . ?
C1 C2 C3 N2 112.34(13) . . . . ?
C3 N2 C4 O2 161.60(15) . . . . ?
C15 N2 C4 O2 -11.5(2) . . . . ?
C3 N2 C4 C5 -17.63(15) . . . . ?
C15 N2 C4 C5 169.22(12) . . . . ?
O2 C4 C5 C2 -164.16(14) . . . . ?
N2 C4 C5 C2 15.07(14) . . . . ?
O2 C4 C5 C6 82.25(18) . . . . ?
N2 C4 C5 C6 -98.52(13) . . . . ?
C3 C2 C5 C4 -7.22(14) . . . . ?
C1 C2 C5 C4 -128.53(12) . . . . ?
C3 C2 C5 C6 111.51(12) . . . . ?
C1 C2 C5 C6 -9.80(14) . . . . ?
C1 N1 C6 C7 163.00(11) . . . . ?
C1 N1 C6 C5 38.61(14) . . . . ?
C4 C5 C6 N1 97.22(13) . . . . ?
C2 C5 C6 N1 -16.01(14) . . . . ?
C4 C5 C6 C7 -24.48(16) . . . . ?
C2 C5 C6 C7 -137.71(12) . . . . ?
N1 C6 C7 C12 -25.56(18) . . . . ?
C5 C6 C7 C12 90.88(16) . . . . ?
N1 C6 C7 C8 155.55(13) . . . . ?
C5 C6 C7 C8 -88.01(16) . . . . ?
C12 C7 C8 C9 -0.8(2) . . . . ?
C6 C7 C8 C9 178.08(13) . . . . ?
C12 C7 C8 N3 -179.40(14) . . . . ?
C6 C7 C8 N3 -0.47(19) . . . . ?
N4 N3 C8 C9 10.2(2) . . . . ?
N4 N3 C8 C7 -171.29(15) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
N3 C8 C9 C10 178.72(15) . . . . ?
C8 C9 C10 C11 0.4(2) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C8 C7 C12 C11 0.8(2) . . . . ?
C6 C7 C12 C11 -178.15(14) . . . . ?
C10 C11 C12 C7 -0.1(3) . . . . ?
C3 N2 C15 C17A 5.5(8) . . . . ?
C4 N2 C15 C17A 177.8(8) . . . . ?
C3 N2 C15 C16 -63.3(3) . . . . ?
C4 N2 C15 C16 109.0(2) . . . . ?
C3 N2 C15 C18 170.7(2) . . . . ?
C4 N2 C15 C18 -17.0(3) . . . . ?
C3 N2 C15 C18A 133.7(6) . . . . ?
C4 N2 C15 C18A -54.1(6) . . . . ?
C3 N2 C15 C17 54.9(2) . . . . ?
C4 N2 C15 C17 -132.86(19) . . . . ?
C3 N2 C15 C16A -113.7(6) . . . . ?
C4 N2 C15 C16A 58.6(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C16 H16B O1 0.96 2.45 3.066(4) 122.0 .
C17 H17C O1 0.96 2.36 3.003(3) 124.0 .
C16A H16E N3 0.96 2.57 3.423(11) 148.6 4_566
C16A H16F O2 0.96 2.43 2.998(12) 117.6 .
C18A H18E O2 0.96 2.45 3.119(12) 126.6 .
N1 H1 O1 0.86(2) 2.56(2) 3.3187(18) 148.3(17) 4_565

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.029

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_umd2944k_a
_database_code_depnum_ccdc_archive 'CCDC 2450976'
loop_
_audit_author_name
_audit_author_address
'James A. Golen'
;UMass Dartmouth
United States of America
;
_audit_update_record             
;
2025-05-13 deposited with the CCDC.	2025-10-01 downloaded from the CCDC.
;

_alert                           
; 
	
  platon level A alert 609 A associted with ABIN solvent void 
  Total solvent accessible volume / cell = 390.7 Ang^3 [5.2%]
  Total electron count / cell = 23.4 
  No change wad made to chemical formula iinforomation 
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 N3 O'
_chemical_formula_weight         269.34

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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   24.7774(12)
_cell_length_b                   24.7774(12)
_cell_length_c                   14.0219(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7455.0(9)
_cell_formula_units_Z            18
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9942
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      24.28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.080
_exptl_crystal_F_000             2592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-IV photon 200'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45868
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.901
_diffrn_reflns_theta_max         25.402
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3029
_reflns_number_gt                2175
_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. 
  
 Structure factors included contributions from the .fab file. 
 OLEX masking progam indicate void volume asociated with solvent
  
  Total solvent accessible volume / cell = 390.7 Ang^3 [5.2%]
  Total electron count / cell = 23.4 
  No change wad made to chemical formula iinforomation  

 _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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1395P)²+4.6237P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   'Fourier difference maps'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3029
_refine_ls_number_parameters     236
_refine_ls_number_restraints     71
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.2328
_refine_ls_wR_factor_gt          0.2002
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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 0.6751(8) 0.8239(6) 0.4435(9) 0.109(3) Uani 0.53(3) 1 d D U P A 1
N2 N 0.6168(6) 0.7227(4) 0.4375(8) 0.066(2) Uani 0.53(3) 1 d D U P A 1
O1A O 0.6990(10) 0.8450(7) 0.4340(10) 0.113(4) Uani 0.47(3) 1 d D U P A 2
N2A N 0.6360(7) 0.7326(7) 0.4312(12) 0.084(3) Uani 0.47(3) 1 d D U P A 2
N1 N 0.75670(10) 0.71098(9) 0.45362(13) 0.0704(6) Uani 1 1 d . . . . .
N3 N 0.59921(10) 0.62241(12) 0.44150(14) 0.0757(6) Uani 1 1 d . . . . .
C1 C 0.77960(15) 0.77590(13) 0.42508(19) 0.0898(9) Uani 1 1 d . . . . .
C2 C 0.72371(15) 0.76987(13) 0.36348(18) 0.0890(8) Uani 1 1 d D . . . .
H2A H 0.7381 0.7955 0.3057 0.107 Uiso 0.53(3) 1 calc R U P A 1
H2B H 0.7397 0.7937 0.3043 0.107 Uiso 0.47(3) 1 calc R U P A 2
C3 C 0.6733(5) 0.7762(6) 0.4144(12) 0.089(3) Uani 0.53(3) 1 d D U P A 1
C3A C 0.6862(7) 0.7920(7) 0.4165(15) 0.091(3) Uani 0.47(3) 1 d D U P A 2
C4 C 0.63204(13) 0.67709(14) 0.40779(15) 0.0721(7) Uani 1 1 d . . . . .
C6 C 0.58458(13) 0.51838(15) 0.4398(2) 0.0872(8) Uani 1 1 d . . . . .
H6 H 0.5432 0.5027 0.4575 0.105 Uiso 1 1 calc R U . . .
C5 C 0.62242(11) 0.58164(12) 0.42289(15) 0.0675(6) Uani 1 1 d . . . . .
C7 C 0.60828(17) 0.47827(14) 0.4303(2) 0.0964(9) Uani 1 1 d . . . . .
H7 H 0.5825 0.4358 0.4412 0.116 Uiso 1 1 calc R U . . .
C8 C 0.66833(17) 0.50024(16) 0.4056(2) 0.0961(9) Uani 1 1 d . . . . .
H8 H 0.6842 0.4733 0.4010 0.115 Uiso 1 1 calc R U . . .
C9 C 0.70591(13) 0.56287(14) 0.38703(19) 0.0815(8) Uani 1 1 d . . . . .
H9 H 0.7471 0.5777 0.3689 0.098 Uiso 1 1 calc R U . . .
C10 C 0.68424(11) 0.60421(11) 0.39461(15) 0.0659(6) Uani 1 1 d . . . . .
C11 C 0.72472(11) 0.67158(12) 0.37069(14) 0.0675(6) Uani 1 1 d . . . . .
H11 H 0.7548 0.6770 0.3209 0.081 Uiso 1 1 calc R U . . .
C12 C 0.68624(12) 0.70051(12) 0.34056(15) 0.0720(7) Uani 1 1 d . . . . .
H12 H 0.6734 0.6923 0.2736 0.086 Uiso 1 1 calc R U . . .
C13 C 0.83787(18) 0.8019(2) 0.3615(3) 0.1324(15) Uani 1 1 d . . . . .
H13A H 0.8505 0.8440 0.3438 0.199 Uiso 1 1 calc R U . . .
H13B H 0.8285 0.7768 0.3052 0.199 Uiso 1 1 calc R U . . .
H13C H 0.8710 0.8012 0.3959 0.199 Uiso 1 1 calc R U . . .
C14 C 0.7937(2) 0.81517(16) 0.5147(2) 0.1213(13) Uani 1 1 d . . . . .
H14A H 0.8086 0.8578 0.4972 0.182 Uiso 1 1 calc R U . . .
H14B H 0.8249 0.8124 0.5514 0.182 Uiso 1 1 calc R U . . .
H14C H 0.7564 0.8001 0.5520 0.182 Uiso 1 1 calc R U . . .
C15 C 0.5636(5) 0.7099(5) 0.4976(4) 0.066(3) Uani 0.48(2) 1 d D U P A 1
H15A H 0.5741 0.7461 0.5369 0.079 Uiso 0.48(2) 1 calc R U P A 1
H15B H 0.5544 0.6753 0.5397 0.079 Uiso 0.48(2) 1 calc R U P A 1
C16 C 0.5077(6) 0.6947(7) 0.4401(10) 0.097(3) Uani 0.48(2) 1 d D U P A 1
H16A H 0.4782 0.6994 0.4786 0.146 Uiso 0.48(2) 1 calc R U P A 1
H16B H 0.4890 0.6525 0.4180 0.146 Uiso 0.48(2) 1 calc R U P A 1
H16C H 0.5195 0.7224 0.3864 0.146 Uiso 0.48(2) 1 calc R U P A 1
C15A C 0.5888(7) 0.7347(7) 0.4917(6) 0.092(3) Uani 0.52(2) 1 d D U P A 2
H15C H 0.6061 0.7765 0.5173 0.110 Uiso 0.52(2) 1 calc R U P A 2
H15D H 0.5800 0.7066 0.5452 0.110 Uiso 0.52(2) 1 calc R U P A 2
C16A C 0.5290(7) 0.7177(8) 0.4429(9) 0.109(3) Uani 0.52(2) 1 d D U P A 2
H16D H 0.4984 0.7128 0.4894 0.164 Uiso 0.52(2) 1 calc R U P A 2
H16E H 0.5146 0.6793 0.4088 0.164 Uiso 0.52(2) 1 calc R U P A 2
H16F H 0.5354 0.7501 0.3989 0.164 Uiso 0.52(2) 1 calc R U P A 2
H1 H 0.7885(13) 0.7071(12) 0.477(2) 0.082(8) Uiso 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
O1 C3 1.230(5) . ?
N2 C3 1.403(5) . ?
N2 C4 1.422(10) . ?
N2 C15 1.459(9) . ?
O1A C3A 1.212(5) . ?
N2A C4 1.369(14) . ?
N2A C3A 1.390(5) . ?
N2A C15A 1.466(9) . ?
N1 C1 1.469(3) . ?
N1 C11 1.469(3) . ?
N1 H1 0.90(3) . ?
N3 C4 1.272(3) . ?
N3 C5 1.414(3) . ?
C1 C14 1.519(4) . ?
C1 C13 1.537(5) . ?
C1 C2 1.575(4) . ?
C2 C3A 1.492(5) . ?
C2 C3 1.515(5) . ?
C2 C12 1.524(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C4 C12 1.500(4) . ?
C6 C7 1.390(4) . ?
C6 C5 1.386(4) . ?
C6 H6 0.9300 . ?
C5 C10 1.400(3) . ?
C7 C8 1.349(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.494(3) . ?
C11 C12 1.512(3) . ?
C11 H11 0.9800 . ?
C12 H12 0.9800 . ?
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 1.479(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15A C16A 1.490(8) . ?
C15A H15C 0.9700 . ?
C15A H15D 0.9700 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?

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
C3 N2 C4 98.5(9) . . ?
C3 N2 C15 134.8(9) . . ?
C4 N2 C15 124.6(7) . . ?
C4 N2A C3A 127.2(10) . . ?
C4 N2A C15A 121.2(11) . . ?
C3A N2A C15A 110.8(11) . . ?
C1 N1 C11 107.26(18) . . ?
C1 N1 H1 109.7(17) . . ?
C11 N1 H1 115.4(18) . . ?
C4 N3 C5 114.8(2) . . ?
N1 C1 C14 108.4(2) . . ?
N1 C1 C13 112.6(3) . . ?
C14 C1 C13 110.1(3) . . ?
N1 C1 C2 101.9(2) . . ?
C14 C1 C2 115.1(3) . . ?
C13 C1 C2 108.6(2) . . ?
C3A C2 C12 112.3(6) . . ?
C3 C2 C12 98.5(5) . . ?
C3A C2 C1 111.8(9) . . ?
C3 C2 C1 117.6(8) . . ?
C12 C2 C1 103.5(2) . . ?
C3 C2 H2A 112.0 . . ?
C12 C2 H2A 112.0 . . ?
C1 C2 H2A 112.0 . . ?
C3A C2 H2B 109.7 . . ?
C12 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
O1 C3 N2 111.8(10) . . ?
O1 C3 C2 128.4(9) . . ?
N2 C3 C2 119.7(9) . . ?
O1A C3A N2A 136.8(12) . . ?
O1A C3A C2 128.8(11) . . ?
N2A C3A C2 94.4(8) . . ?
N3 C4 N2A 131.8(7) . . ?
N3 C4 N2 117.0(5) . . ?
N3 C4 C12 128.1(2) . . ?
N2A C4 C12 99.3(6) . . ?
N2 C4 C12 114.8(5) . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C5 C10 119.1(2) . . ?
C6 C5 N3 119.3(2) . . ?
C10 C5 N3 121.4(2) . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.4(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C10 121.9(3) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C9 C10 C5 118.7(2) . . ?
C9 C10 C11 121.3(2) . . ?
C5 C10 C11 119.9(2) . . ?
N1 C11 C10 113.73(17) . . ?
N1 C11 C12 99.48(19) . . ?
C10 C11 C12 111.3(2) . . ?
N1 C11 H11 110.6 . . ?
C10 C11 H11 110.6 . . ?
C12 C11 H11 110.6 . . ?
C4 C12 C11 107.21(19) . . ?
C4 C12 C2 103.1(2) . . ?
C11 C12 C2 107.6(2) . . ?
C4 C12 H12 112.8 . . ?
C11 C12 H12 112.8 . . ?
C2 C12 H12 112.8 . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C16 111.7(8) . . ?
N2 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
N2 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2A C15A C16A 115.0(10) . . ?
N2A C15A H15C 108.5 . . ?
C16A C15A H15C 108.5 . . ?
N2A C15A H15D 108.5 . . ?
C16A C15A H15D 108.5 . . ?
H15C C15A H15D 107.5 . . ?
C15A C16A H16D 109.5 . . ?
C15A C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
C15A C16A H16F 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 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
C11 N1 C1 C14 161.9(3) . . . . ?
C11 N1 C1 C13 -76.0(3) . . . . ?
C11 N1 C1 C2 40.1(3) . . . . ?
N1 C1 C2 C3A 104.0(7) . . . . ?
C14 C1 C2 C3A -13.0(7) . . . . ?
C13 C1 C2 C3A -136.9(7) . . . . ?
N1 C1 C2 C3 90.2(6) . . . . ?
C14 C1 C2 C3 -26.8(6) . . . . ?
C13 C1 C2 C3 -150.7(6) . . . . ?
N1 C1 C2 C12 -17.1(3) . . . . ?
C14 C1 C2 C12 -134.1(3) . . . . ?
C13 C1 C2 C12 102.0(3) . . . . ?
C4 N2 C3 O1 -172.4(14) . . . . ?
C15 N2 C3 O1 -9(3) . . . . ?
C4 N2 C3 C2 5.1(17) . . . . ?
C15 N2 C3 C2 168.1(11) . . . . ?
C12 C2 C3 O1 -173.9(18) . . . . ?
C1 C2 C3 O1 76(2) . . . . ?
C12 C2 C3 N2 9.1(16) . . . . ?
C1 C2 C3 N2 -101.0(14) . . . . ?
C4 N2A C3A O1A -177(2) . . . . ?
C15A N2A C3A O1A -7(4) . . . . ?
C4 N2A C3A C2 5(2) . . . . ?
C15A N2A C3A C2 174.9(12) . . . . ?
C12 C2 C3A O1A -169(2) . . . . ?
C1 C2 C3A O1A 75(2) . . . . ?
C12 C2 C3A N2A 8.9(16) . . . . ?
C1 C2 C3A N2A -106.9(13) . . . . ?
C5 N3 C4 N2A -159.0(10) . . . . ?
C5 N3 C4 N2 -169.9(6) . . . . ?
C5 N3 C4 C12 9.3(3) . . . . ?
C3A N2A C4 N3 155.1(16) . . . . ?
C15A N2A C4 N3 -14.1(19) . . . . ?
C3A N2A C4 C12 -16(2) . . . . ?
C15A N2A C4 C12 175.2(12) . . . . ?
C3 N2 C4 N3 160.5(9) . . . . ?
C15 N2 C4 N3 -4.9(13) . . . . ?
C3 N2 C4 C12 -18.8(12) . . . . ?
C15 N2 C4 C12 175.9(8) . . . . ?
C7 C6 C5 C10 1.2(4) . . . . ?
C7 C6 C5 N3 -174.1(2) . . . . ?
C4 N3 C5 C6 -167.5(2) . . . . ?
C4 N3 C5 C10 17.3(3) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C6 C7 C8 C9 -1.7(5) . . . . ?
C7 C8 C9 C10 1.1(4) . . . . ?
C8 C9 C10 C5 0.6(4) . . . . ?
C8 C9 C10 C11 -177.6(2) . . . . ?
C6 C5 C10 C9 -1.8(3) . . . . ?
N3 C5 C10 C9 173.4(2) . . . . ?
C6 C5 C10 C11 176.5(2) . . . . ?
N3 C5 C10 C11 -8.3(3) . . . . ?
C1 N1 C11 C10 -164.3(2) . . . . ?
C1 N1 C11 C12 -46.0(2) . . . . ?
C9 C10 C11 N1 -94.7(3) . . . . ?
C5 C10 C11 N1 87.0(3) . . . . ?
C9 C10 C11 C12 153.9(2) . . . . ?
C5 C10 C11 C12 -24.3(3) . . . . ?
N3 C4 C12 C11 -40.4(3) . . . . ?
N2A C4 C12 C11 130.8(8) . . . . ?
N2 C4 C12 C11 138.8(6) . . . . ?
N3 C4 C12 C2 -153.8(2) . . . . ?
N2A C4 C12 C2 17.4(8) . . . . ?
N2 C4 C12 C2 25.4(6) . . . . ?
N1 C11 C12 C4 -77.2(2) . . . . ?
C10 C11 C12 C4 42.9(2) . . . . ?
N1 C11 C12 C2 33.1(2) . . . . ?
C10 C11 C12 C2 153.25(19) . . . . ?
C3A C2 C12 C4 -17.7(10) . . . . ?
C3 C2 C12 C4 -18.2(8) . . . . ?
C1 C2 C12 C4 103.0(2) . . . . ?
C3A C2 C12 C11 -130.8(10) . . . . ?
C3 C2 C12 C11 -131.3(7) . . . . ?
C1 C2 C12 C11 -10.1(3) . . . . ?
C3 N2 C15 C16 109.4(17) . . . . ?
C4 N2 C15 C16 -91.2(12) . . . . ?
C4 N2A C15A C16A -77.0(16) . . . . ?
C3A N2A C15A C16A 112.1(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12 N1 0.98 2.66 3.549(3) 150.5 8_654
N1 H1 O1 0.90(3) 2.35(3) 3.229(11) 166(2) 12_656
N1 H1 O1A 0.90(3) 2.13(3) 3.016(11) 166(3) 12_656

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.053

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_umd2960f_a
_database_code_depnum_ccdc_archive 'CCDC 2450975'
loop_
_audit_author_name
_audit_author_address
'James A. Golen'
;UMass Dartmouth
United States of America
;
_audit_update_record             
;
2025-05-13 deposited with the CCDC.	2025-10-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 N5 O2'
_chemical_formula_weight         299.33

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                   14.0582(13)
_cell_length_b                   8.7981(7)
_cell_length_c                   13.4520(12)
_cell_angle_alpha                90
_cell_angle_beta                 111.489(3)
_cell_angle_gamma                90
_cell_volume                     1548.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      26.28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.701
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-IV photon 200'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33191
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.051
_diffrn_reflns_theta_max         26.384
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3141
_reflns_number_gt                2618
_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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0617P)²+0.4258P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   'Fourier difference maps'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3141
_refine_ls_number_parameters     217
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.008
_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 0.08369(10) 0.31033(18) -0.01586(9) 0.0766(4) Uani 1 1 d . . . . .
O2 O 0.39105(10) 0.41713(18) 0.23661(10) 0.0814(5) Uani 1 1 d . . . . .
N1 N 0.14361(9) 0.21336(16) 0.28128(9) 0.0455(3) Uani 1 1 d . . . . .
H1 H 0.1153(14) 0.196(2) 0.3286(15) 0.063(5) Uiso 1 1 d . . . . .
N2 N 0.23071(11) 0.40039(15) 0.10950(10) 0.0546(3) Uani 1 1 d D U . . .
N3 N 0.43702(10) 0.17272(15) 0.50938(10) 0.0546(3) Uani 1 1 d . . . . .
N4 N 0.51663(10) 0.16056(17) 0.58896(11) 0.0599(4) Uani 1 1 d . . . . .
N5 N 0.58944(13) 0.1361(2) 0.65828(15) 0.0897(6) Uani 1 1 d . . . . .
C1 C 0.10829(11) 0.10932(18) 0.18942(11) 0.0460(4) Uani 1 1 d . . . . .
C2 C 0.18467(10) 0.15260(16) 0.13532(10) 0.0385(3) Uani 1 1 d . . . . .
H2A H 0.1963 0.0663 0.0951 0.046 Uiso 1 1 calc R U . . .
C3 C 0.15637(11) 0.29236(19) 0.06635(11) 0.0474(4) Uani 1 1 d . . . . .
C4 C 0.31216(12) 0.34858(19) 0.19620(11) 0.0495(4) Uani 1 1 d . . . . .
C5 C 0.28392(9) 0.19638(16) 0.22729(10) 0.0384(3) Uani 1 1 d . . . . .
H5A H 0.3379 0.1213 0.2361 0.046 Uiso 1 1 calc R U . . .
C6 C 0.25465(10) 0.20384(16) 0.32876(10) 0.0380(3) Uani 1 1 d . . . . .
H6A H 0.2738 0.1078 0.3679 0.046 Uiso 1 1 calc R U . . .
C7 C 0.29900(9) 0.33428(16) 0.40528(9) 0.0366(3) Uani 1 1 d . . . . .
C8 C 0.38791(10) 0.31803(16) 0.49538(10) 0.0387(3) Uani 1 1 d . . . . .
C9 C 0.42620(11) 0.43737(18) 0.56619(11) 0.0467(3) Uani 1 1 d . . . . .
H9A H 0.4852 0.4241 0.6264 0.056 Uiso 1 1 calc R U . . .
C10 C 0.37671(12) 0.57537(19) 0.54717(13) 0.0532(4) Uani 1 1 d . . . . .
H10A H 0.4021 0.6556 0.5946 0.064 Uiso 1 1 calc R U . . .
C11 C 0.28928(12) 0.59452(19) 0.45761(13) 0.0558(4) Uani 1 1 d . . . . .
H11A H 0.2561 0.6880 0.4442 0.067 Uiso 1 1 calc R U . . .
C12 C 0.25128(11) 0.47506(18) 0.38807(12) 0.0478(4) Uani 1 1 d . . . . .
H12A H 0.1922 0.4892 0.3281 0.057 Uiso 1 1 calc R U . . .
C13 C 0.12131(16) -0.0589(2) 0.21983(15) 0.0714(5) Uani 1 1 d . . . . .
H13A H 0.0945 -0.1199 0.1564 0.107 Uiso 1 1 calc R U . . .
H13B H 0.0851 -0.0814 0.2662 0.107 Uiso 1 1 calc R U . . .
H13C H 0.1926 -0.0812 0.2559 0.107 Uiso 1 1 calc R U . . .
C14 C -0.00378(12) 0.1435(3) 0.12532(14) 0.0685(5) Uani 1 1 d . . . . .
H14C H -0.0264 0.0832 0.0614 0.103 Uiso 1 1 calc R U . . .
H14B H -0.0115 0.2493 0.1067 0.103 Uiso 1 1 calc R U . . .
H14A H -0.0440 0.1194 0.1675 0.103 Uiso 1 1 calc R U . . .
C15 C 0.2420(10) 0.5491(8) 0.0645(10) 0.076(2) Uani 0.57(3) 1 d D U P A 1
H15A H 0.2495 0.6270 0.1168 0.114 Uiso 0.57(3) 1 calc R U P A 1
H15B H 0.1824 0.5694 0.0023 0.114 Uiso 0.57(3) 1 calc R U P A 1
H15C H 0.3013 0.5476 0.0453 0.114 Uiso 0.57(3) 1 calc R U P A 1
C15A C 0.2099(16) 0.5537(12) 0.0607(14) 0.091(4) Uani 0.43(3) 1 d D U P A 2
H15D H 0.2568 0.6254 0.1071 0.136 Uiso 0.43(3) 1 calc R U P A 2
H15E H 0.1411 0.5830 0.0504 0.136 Uiso 0.43(3) 1 calc R U P A 2
H15F H 0.2181 0.5520 -0.0070 0.136 Uiso 0.43(3) 1 calc R U P A 2


_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 C3 1.2101(18) . ?
O2 C4 1.2032(18) . ?
N1 C6 1.4564(17) . ?
N1 C1 1.4703(18) . ?
N1 H1 0.878(19) . ?
N2 C3 1.374(2) . ?
N2 C4 1.379(2) . ?
N2 C15 1.474(6) . ?
N2 C15A 1.482(8) . ?
N3 N4 1.2377(17) . ?
N3 C8 1.4323(19) . ?
N4 N5 1.1244(19) . ?
C1 C14 1.523(2) . ?
C1 C13 1.529(3) . ?
C1 C2 1.5493(19) . ?
C2 C3 1.503(2) . ?
C2 C5 1.5365(17) . ?
C2 H2A 0.9800 . ?
C4 C5 1.499(2) . ?
C5 C6 1.5647(17) . ?
C5 H5A 0.9800 . ?
C6 C7 1.5150(18) . ?
C6 H6A 0.9800 . ?
C7 C12 1.387(2) . ?
C7 C8 1.3935(17) . ?
C8 C9 1.387(2) . ?
C9 C10 1.376(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.381(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.378(2) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14C 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14A 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15A H15D 0.9600 . ?
C15A H15E 0.9600 . ?
C15A H15F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C1 108.09(11) . . ?
C6 N1 H1 111.7(12) . . ?
C1 N1 H1 113.5(12) . . ?
C3 N2 C4 113.34(13) . . ?
C3 N2 C15 128.3(6) . . ?
C4 N2 C15 117.4(6) . . ?
C3 N2 C15A 116.5(7) . . ?
C4 N2 C15A 130.1(7) . . ?
N4 N3 C8 115.50(13) . . ?
N5 N4 N3 173.60(19) . . ?
N1 C1 C14 108.28(13) . . ?
N1 C1 C13 114.05(13) . . ?
C14 C1 C13 109.88(14) . . ?
N1 C1 C2 99.38(10) . . ?
C14 C1 C2 115.89(13) . . ?
C13 C1 C2 109.15(14) . . ?
C3 C2 C5 104.41(11) . . ?
C3 C2 C1 114.75(12) . . ?
C5 C2 C1 105.33(10) . . ?
C3 C2 H2A 110.7 . . ?
C5 C2 H2A 110.7 . . ?
C1 C2 H2A 110.7 . . ?
O1 C3 N2 123.55(16) . . ?
O1 C3 C2 127.94(15) . . ?
N2 C3 C2 108.46(12) . . ?
O2 C4 N2 123.99(17) . . ?
O2 C4 C5 128.04(16) . . ?
N2 C4 C5 107.97(12) . . ?
C4 C5 C2 104.74(11) . . ?
C4 C5 C6 112.78(11) . . ?
C2 C5 C6 105.16(10) . . ?
C4 C5 H5A 111.3 . . ?
C2 C5 H5A 111.3 . . ?
C6 C5 H5A 111.3 . . ?
N1 C6 C7 111.26(11) . . ?
N1 C6 C5 101.65(9) . . ?
C7 C6 C5 116.75(11) . . ?
N1 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C12 C7 C8 117.49(12) . . ?
C12 C7 C6 120.63(11) . . ?
C8 C7 C6 121.87(12) . . ?
C9 C8 C7 121.23(13) . . ?
C9 C8 N3 122.56(12) . . ?
C7 C8 N3 116.20(12) . . ?
C10 C9 C8 119.85(13) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C11 119.86(14) . . ?
C9 C10 H10A 120.1 . . ?
C11 C10 H10A 120.1 . . ?
C12 C11 C10 119.94(15) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C11 C12 C7 121.62(14) . . ?
C11 C12 H12A 119.2 . . ?
C7 C12 H12A 119.2 . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C14 H14C 109.5 . . ?
C1 C14 H14B 109.5 . . ?
H14C C14 H14B 109.5 . . ?
C1 C14 H14A 109.5 . . ?
H14C C14 H14A 109.5 . . ?
H14B C14 H14A 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C15A H15D 109.5 . . ?
N2 C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?
N2 C15A H15F 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C1 C14 -167.81(13) . . . . ?
C6 N1 C1 C13 69.53(16) . . . . ?
C6 N1 C1 C2 -46.43(14) . . . . ?
N1 C1 C2 C3 -81.84(13) . . . . ?
C14 C1 C2 C3 33.86(18) . . . . ?
C13 C1 C2 C3 158.52(12) . . . . ?
N1 C1 C2 C5 32.40(14) . . . . ?
C14 C1 C2 C5 148.10(14) . . . . ?
C13 C1 C2 C5 -87.24(13) . . . . ?
C4 N2 C3 O1 -172.70(14) . . . . ?
C15 N2 C3 O1 -4.4(6) . . . . ?
C15A N2 C3 O1 10.2(10) . . . . ?
C4 N2 C3 C2 4.81(17) . . . . ?
C15 N2 C3 C2 173.1(6) . . . . ?
C15A N2 C3 C2 -172.3(10) . . . . ?
C5 C2 C3 O1 179.50(15) . . . . ?
C1 C2 C3 O1 -65.7(2) . . . . ?
C5 C2 C3 N2 2.13(15) . . . . ?
C1 C2 C3 N2 116.90(13) . . . . ?
C3 N2 C4 O2 169.56(15) . . . . ?
C15 N2 C4 O2 -0.1(6) . . . . ?
C15A N2 C4 O2 -13.8(12) . . . . ?
C3 N2 C4 C5 -9.88(16) . . . . ?
C15 N2 C4 C5 -179.6(5) . . . . ?
C15A N2 C4 C5 166.8(11) . . . . ?
O2 C4 C5 C2 -168.93(15) . . . . ?
N2 C4 C5 C2 10.47(14) . . . . ?
O2 C4 C5 C6 77.25(19) . . . . ?
N2 C4 C5 C6 -103.34(12) . . . . ?
C3 C2 C5 C4 -7.47(13) . . . . ?
C1 C2 C5 C4 -128.71(12) . . . . ?
C3 C2 C5 C6 111.61(12) . . . . ?
C1 C2 C5 C6 -9.63(14) . . . . ?
C1 N1 C6 C7 165.65(11) . . . . ?
C1 N1 C6 C5 40.67(14) . . . . ?
C4 C5 C6 N1 96.29(13) . . . . ?
C2 C5 C6 N1 -17.27(13) . . . . ?
C4 C5 C6 C7 -24.95(16) . . . . ?
C2 C5 C6 C7 -138.51(12) . . . . ?
N1 C6 C7 C12 -31.39(17) . . . . ?
C5 C6 C7 C12 84.64(15) . . . . ?
N1 C6 C7 C8 148.06(12) . . . . ?
C5 C6 C7 C8 -95.91(15) . . . . ?
C12 C7 C8 C9 1.12(19) . . . . ?
C6 C7 C8 C9 -178.35(12) . . . . ?
C12 C7 C8 N3 -178.29(12) . . . . ?
C6 C7 C8 N3 2.24(18) . . . . ?
N4 N3 C8 C9 -0.3(2) . . . . ?
N4 N3 C8 C7 179.07(13) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
N3 C8 C9 C10 178.61(14) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C10 C11 C12 C7 -0.2(2) . . . . ?
C8 C7 C12 C11 -0.6(2) . . . . ?
C6 C7 C12 C11 178.85(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.878(19) 2.29(2) 3.1438(18) 162.9(16) 4_566
C5 H5A N5 0.98 2.67 3.477(2) 139.8 3_656
C9 H9A O2 0.93 2.45 3.2067(18) 138.0 3_666

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.029

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_umd2959d_a
_database_code_depnum_ccdc_archive 'CCDC 2450977'
loop_
_audit_author_name
_audit_author_address
'James A. Golen'
;UMass Dartmouth
United States of America
;
_audit_update_record             
;
2025-05-13 deposited with the CCDC.	2025-10-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 N3 O'
_chemical_formula_weight         241.29

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                   10.1162(7)
_cell_length_b                   11.1065(9)
_cell_length_c                   10.7813(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.768(3)
_cell_angle_gamma                90
_cell_volume                     1190.01(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    8604
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      26.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.340
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-IV photon 200'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14404
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.062
_diffrn_reflns_theta_max         26.396
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2441
_reflns_number_gt                2126
_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 APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0484P)²+0.3207P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   'Fourier difference maps'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2441
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.51860(12) 0.21462(11) 0.82413(10) 0.0631(3) Uani 1 1 d . . . . .
N1 N 0.33351(11) 0.55809(9) 0.69784(9) 0.0373(3) Uani 1 1 d . . . . .
N2 N 0.45453(10) 0.26564(9) 0.61528(10) 0.0377(3) Uani 1 1 d . . . . .
N3 N 0.38014(10) 0.39112(9) 0.44097(9) 0.0343(2) Uani 1 1 d . . . . .
C1 C 0.36380(14) 0.47375(13) 0.80611(12) 0.0433(3) Uani 1 1 d . . . . .
H1A H 0.4605 0.4756 0.8410 0.052 Uiso 1 1 calc R U . . .
C2 C 0.32316(13) 0.34457(12) 0.75387(12) 0.0415(3) Uani 1 1 d . . . . .
H2A H 0.2633 0.3044 0.8026 0.050 Uiso 1 1 calc R U . . .
C3 C 0.44242(13) 0.26636(12) 0.74094(13) 0.0430(3) Uani 1 1 d . . . . .
C4 C 0.36338(11) 0.34352(10) 0.54467(11) 0.0326(3) Uani 1 1 d . . . . .
C5 C 0.28538(11) 0.48276(11) 0.39500(11) 0.0330(3) Uani 1 1 d . . . . .
C6 C 0.27332(13) 0.51805(13) 0.26977(12) 0.0411(3) Uani 1 1 d . . . . .
H6A H 0.3243 0.4797 0.2181 0.049 Uiso 1 1 calc R U . . .
C7 C 0.18654(14) 0.60934(14) 0.22125(13) 0.0478(3) Uani 1 1 d . . . . .
H7A H 0.1796 0.6323 0.1373 0.057 Uiso 1 1 calc R U . . .
C8 C 0.10955(14) 0.66713(13) 0.29687(13) 0.0465(3) Uani 1 1 d . . . . .
H8A H 0.0502 0.7280 0.2637 0.056 Uiso 1 1 calc R U . . .
C9 C 0.12180(12) 0.63345(12) 0.42251(12) 0.0390(3) Uani 1 1 d . . . . .
H9A H 0.0705 0.6724 0.4735 0.047 Uiso 1 1 calc R U . . .
C10 C 0.20962(11) 0.54239(10) 0.47307(11) 0.0322(3) Uani 1 1 d . . . . .
C11 C 0.22147(12) 0.50211(11) 0.60806(11) 0.0335(3) Uani 1 1 d . . . . .
H11A H 0.1364 0.5174 0.6363 0.040 Uiso 1 1 calc R U . . .
C12 C 0.25325(12) 0.36832(11) 0.61809(12) 0.0356(3) Uani 1 1 d . . . . .
H12A H 0.1737 0.3177 0.5916 0.043 Uiso 1 1 calc R U . . .
C13 C 0.2857(2) 0.50837(17) 0.90843(15) 0.0675(5) Uani 1 1 d . . . . .
H13A H 0.3035 0.4510 0.9761 0.101 Uiso 1 1 calc R U . . .
H13B H 0.1911 0.5089 0.8737 0.101 Uiso 1 1 calc R U . . .
H13C H 0.3130 0.5871 0.9401 0.101 Uiso 1 1 calc R U . . .
C14 C 0.56581(13) 0.20877(13) 0.57020(14) 0.0448(3) Uani 1 1 d . . . . .
H14A H 0.5545 0.2188 0.4804 0.067 Uiso 0.5 1 calc R U P . .
H14B H 0.6488 0.2454 0.6102 0.067 Uiso 0.5 1 calc R U P . .
H14C H 0.5677 0.1245 0.5902 0.067 Uiso 0.5 1 calc R U P . .
H14D H 0.6262 0.1736 0.6401 0.067 Uiso 0.5 1 calc R U P . .
H14E H 0.5319 0.1471 0.5103 0.067 Uiso 0.5 1 calc R U P . .
H14F H 0.6130 0.2680 0.5304 0.067 Uiso 0.5 1 calc R U P . .
H1 H 0.4077(16) 0.5618(13) 0.6589(14) 0.045(4) Uiso 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
O1 C3 1.2126(16) . ?
N1 C1 1.4834(16) . ?
N1 C11 1.4826(15) . ?
N1 H1 0.927(16) . ?
N2 C3 1.3830(18) . ?
N2 C4 1.3841(15) . ?
N2 C14 1.4514(16) . ?
N3 C4 1.2764(16) . ?
N3 C5 1.4223(15) . ?
C1 C13 1.522(2) . ?
C1 C2 1.568(2) . ?
C1 H1A 0.9800 . ?
C2 C3 1.5140(18) . ?
C2 C12 1.5251(18) . ?
C2 H2A 0.9800 . ?
C4 C12 1.5077(16) . ?
C5 C6 1.3892(17) . ?
C5 C10 1.4055(17) . ?
C6 C7 1.379(2) . ?
C6 H6A 0.9300 . ?
C7 C8 1.386(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.3882(19) . ?
C8 H8A 0.9300 . ?
C9 C10 1.3887(17) . ?
C9 H9A 0.9300 . ?
C10 C11 1.5058(16) . ?
C11 C12 1.5199(17) . ?
C11 H11A 0.9800 . ?
C12 H12A 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 H14D 0.9600 . ?
C14 H14E 0.9600 . ?
C14 H14F 0.9600 . ?

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 C11 105.62(10) . . ?
C1 N1 H1 108.6(9) . . ?
C11 N1 H1 108.0(9) . . ?
C3 N2 C4 111.30(10) . . ?
C3 N2 C14 123.14(11) . . ?
C4 N2 C14 124.51(11) . . ?
C4 N3 C5 114.23(10) . . ?
N1 C1 C13 110.61(12) . . ?
N1 C1 C2 107.06(10) . . ?
C13 C1 C2 110.78(12) . . ?
N1 C1 H1A 109.4 . . ?
C13 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
C3 C2 C12 104.21(11) . . ?
C3 C2 C1 113.46(11) . . ?
C12 C2 C1 103.30(10) . . ?
C3 C2 H2A 111.8 . . ?
C12 C2 H2A 111.8 . . ?
C1 C2 H2A 111.8 . . ?
O1 C3 N2 124.16(13) . . ?
O1 C3 C2 127.67(13) . . ?
N2 C3 C2 108.15(11) . . ?
N3 C4 N2 123.83(11) . . ?
N3 C4 C12 128.05(11) . . ?
N2 C4 C12 107.89(10) . . ?
C6 C5 C10 119.37(11) . . ?
C6 C5 N3 118.14(11) . . ?
C10 C5 N3 122.41(10) . . ?
C7 C6 C5 120.68(12) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C6 C7 C8 120.36(12) . . ?
C6 C7 H7A 119.8 . . ?
C8 C7 H7A 119.8 . . ?
C9 C8 C7 119.45(12) . . ?
C9 C8 H8A 120.3 . . ?
C7 C8 H8A 120.3 . . ?
C10 C9 C8 120.88(12) . . ?
C10 C9 H9A 119.6 . . ?
C8 C9 H9A 119.6 . . ?
C9 C10 C5 119.24(11) . . ?
C9 C10 C11 121.69(11) . . ?
C5 C10 C11 119.01(10) . . ?
N1 C11 C10 114.81(10) . . ?
N1 C11 C12 103.76(9) . . ?
C10 C11 C12 109.68(10) . . ?
N1 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C4 C12 C11 107.97(9) . . ?
C4 C12 C2 102.51(10) . . ?
C11 C12 C2 106.94(10) . . ?
C4 C12 H12A 112.9 . . ?
C11 C12 H12A 112.9 . . ?
C2 C12 H12A 112.9 . . ?
C1 C13 H13A 109.5 . . ?
C1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C14 H14D 109.5 . . ?
H14A C14 H14D 141.1 . . ?
H14B C14 H14D 56.3 . . ?
H14C C14 H14D 56.3 . . ?
N2 C14 H14E 109.5 . . ?
H14A C14 H14E 56.3 . . ?
H14B C14 H14E 141.1 . . ?
H14C C14 H14E 56.3 . . ?
H14D C14 H14E 109.5 . . ?
N2 C14 H14F 109.5 . . ?
H14A C14 H14F 56.3 . . ?
H14B C14 H14F 56.3 . . ?
H14C C14 H14F 141.1 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 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
C11 N1 C1 C13 -93.00(14) . . . . ?
C11 N1 C1 C2 27.80(13) . . . . ?
N1 C1 C2 C3 104.80(12) . . . . ?
C13 C1 C2 C3 -134.51(13) . . . . ?
N1 C1 C2 C12 -7.38(13) . . . . ?
C13 C1 C2 C12 113.30(12) . . . . ?
C4 N2 C3 O1 -172.91(13) . . . . ?
C14 N2 C3 O1 -4.2(2) . . . . ?
C4 N2 C3 C2 5.30(14) . . . . ?
C14 N2 C3 C2 174.05(11) . . . . ?
C12 C2 C3 O1 -171.36(14) . . . . ?
C1 C2 C3 O1 77.01(17) . . . . ?
C12 C2 C3 N2 10.52(13) . . . . ?
C1 C2 C3 N2 -101.11(13) . . . . ?
C5 N3 C4 N2 -170.34(10) . . . . ?
C5 N3 C4 C12 3.43(17) . . . . ?
C3 N2 C4 N3 155.47(12) . . . . ?
C14 N2 C4 N3 -13.10(19) . . . . ?
C3 N2 C4 C12 -19.38(13) . . . . ?
C14 N2 C4 C12 172.05(11) . . . . ?
C4 N3 C5 C6 -163.94(11) . . . . ?
C4 N3 C5 C10 19.45(16) . . . . ?
C10 C5 C6 C7 -1.01(19) . . . . ?
N3 C5 C6 C7 -177.73(11) . . . . ?
C5 C6 C7 C8 -0.2(2) . . . . ?
C6 C7 C8 C9 0.9(2) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C8 C9 C10 C5 -0.91(18) . . . . ?
C8 C9 C10 C11 -178.22(12) . . . . ?
C6 C5 C10 C9 1.55(17) . . . . ?
N3 C5 C10 C9 178.12(11) . . . . ?
C6 C5 C10 C11 178.93(11) . . . . ?
N3 C5 C10 C11 -4.50(16) . . . . ?
C1 N1 C11 C10 -156.66(10) . . . . ?
C1 N1 C11 C12 -36.98(12) . . . . ?
C9 C10 C11 N1 -96.35(13) . . . . ?
C5 C10 C11 N1 86.33(13) . . . . ?
C9 C10 C11 C12 147.32(11) . . . . ?
C5 C10 C11 C12 -30.00(14) . . . . ?
N3 C4 C12 C11 -37.23(16) . . . . ?
N2 C4 C12 C11 137.34(10) . . . . ?
N3 C4 C12 C2 -149.92(12) . . . . ?
N2 C4 C12 C2 24.65(12) . . . . ?
N1 C11 C12 C4 -77.26(11) . . . . ?
C10 C11 C12 C4 45.85(12) . . . . ?
N1 C11 C12 C2 32.43(12) . . . . ?
C10 C11 C12 C2 155.54(10) . . . . ?
C3 C2 C12 C4 -20.57(12) . . . . ?
C1 C2 C12 C4 98.24(10) . . . . ?
C3 C2 C12 C11 -134.02(10) . . . . ?
C1 C2 C12 C11 -15.21(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N3 0.927(16) 2.627(16) 3.5453(15) 170.8(13) 3_666

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.031

_shelxl_version_number           2014/6

