# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_rds971
_database_code_depnum_ccdc_archive 'CCDC 2061240'
loop_
_audit_author_name
_audit_author_address
'Roger Sommer'
;North Carolina State University
United States of America
;
_audit_update_record             
;
2021-02-04 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            BL-1-012
_chemical_formula_moiety         'C17 H25 N3 O3'
_chemical_formula_sum            'C17 H25 N3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         319.40

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9857(2)
_cell_length_b                   10.0171(2)
_cell_length_c                   11.6679(2)
_cell_angle_alpha                66.1920(10)
_cell_angle_beta                 82.8390(10)
_cell_angle_gamma                66.4290(10)
_cell_volume                     879.85(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      4.1453
_cell_measurement_theta_max      66.4718
_cell_measurement_temperature    298.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.164
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344

_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;
;

_diffrn_ambient_temperature      298.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            23611
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_theta_min         4.14
_diffrn_reflns_theta_max         66.65
_diffrn_reflns_theta_full        66.65
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
piperidinyl group is disordered over two positions. SAME/SADI restraints were
used to maintain a chemically reasonablemodel for disordered ring.
The H atom on N2 was visible as a Q peak (0.5e⁻/%α³) is difference map. It
was placed using AFIX instructions for initial refinements and then allowed to
refine freely maintaining the isotropic displacement parameter at 1.2x that of
the parent atom.
The difference map also showed the possibility of the second orientation of the
p-methoxy group. This was not modeled because all of the difference map peaks
were at or below 0.50e⁻/%α³.
;

_reflns_number_total             3089
_reflns_number_gt                2635
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_gt          0.2121
_refine_ls_wR_factor_ref         0.2250
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.075
_refine_ls_number_reflns         3089
_refine_ls_number_parameters     268
_refine_ls_number_restraints     12
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1229P)²+0.2374P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.231
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
'Bruker Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, 2019)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5076(2) 0.16563(19) 0.37354(15) 0.0877(6) Uani d . . . 1.0 . .
O O2 0.7556(3) 0.3593(2) 0.43290(18) 0.0968(6) Uani d . . . 1.0 . .
O O3 0.6893(3) 0.2862(3) 1.0731(2) 0.1108(7) Uani d . . . 1.0 . .
N N1 0.6010(2) 0.2292(2) 0.54935(16) 0.0666(5) Uani d . . . 1.0 . .
N N2 0.5979(2) 0.0850(2) 0.63936(17) 0.0704(5) Uani d . . . 1.0 . .
H H2 0.568(3) 0.036(3) 0.603(2) 0.085 Uiso d U . . 1.0 . .
C C1 0.4167(3) 0.2895(3) 0.3814(2) 0.0818(7) Uani d . . . 1.0 . .
C C2 0.4567(3) 0.3458(3) 0.4729(2) 0.0738(6) Uani d . . . 1.0 . .
H H2A 0.472756 0.443658 0.42629 0.089 Uiso calc U . R 1.0 . .
H H2B 0.365986 0.366794 0.526431 0.089 Uiso calc U . R 1.0 . .
C C3 0.7451(3) 0.2434(3) 0.5197(2) 0.0701(6) Uani d . . . 1.0 . .
C C4 0.8902(3) 0.1159(3) 0.6004(3) 0.0897(8) Uani d . . . 1.0 . .
H H4A 0.906098 0.017115 0.596665 0.135 Uiso calc U . R 1.0 . .
H H4B 0.873462 0.107946 0.685411 0.135 Uiso calc U . R 1.0 . .
H H4C 0.984408 0.14052 0.571059 0.135 Uiso calc U . R 1.0 . .
C C5 0.4888(3) 0.1036(3) 0.7403(2) 0.0809(7) Uani d . . . 1.0 . .
H H5A 0.47323 0.005509 0.787242 0.097 Uiso calc U . R 1.0 . .
H H5B 0.383849 0.185341 0.704208 0.097 Uiso calc U . R 1.0 . .
C C6 0.5515(3) 0.1464(3) 0.8287(2) 0.0688(6) Uani d . . . 1.0 . .
C C7 0.6774(3) 0.0381(3) 0.9135(2) 0.0816(7) Uani d . . . 1.0 . .
H H7 0.729681 -0.063578 0.914824 0.098 Uiso calc U . R 1.0 . .
C C8 0.7281(3) 0.0801(3) 0.9986(2) 0.0875(7) Uani d . . . 1.0 . .
H H8 0.81352 0.00727 1.056756 0.105 Uiso calc U . R 1.0 . .
C C9 0.6467(3) 0.2342(3) 0.9935(2) 0.0759(6) Uani d . . . 1.0 . .
C C10 0.5257(4) 0.3412(3) 0.9080(3) 0.0882(7) Uani d . . . 1.0 . .
H H10 0.474928 0.443936 0.904683 0.106 Uiso calc U . R 1.0 . .
C C11 0.4775(3) 0.2991(3) 0.8262(2) 0.0812(7) Uani d . . . 1.0 . .
H H11 0.393384 0.373896 0.767363 0.097 Uiso calc U . R 1.0 . .
C C12 0.8059(4) 0.1784(5) 1.1686(3) 0.1234(13) Uani d . . . 1.0 . .
H H12A 0.905969 0.131968 1.13336 0.185 Uiso calc U . R 1.0 . .
H H12B 0.769504 0.097 1.22353 0.185 Uiso calc U . R 1.0 . .
H H12C 0.823073 0.231506 1.215179 0.185 Uiso calc U . R 1.0 . .
N N3 0.2960(5) 0.3922(5) 0.2994(4) 0.0767(11) Uani d . P D 0.665(6) A 1
C C13 0.1870(5) 0.5458(5) 0.3001(4) 0.0778(12) Uani d . P D 0.665(6) A 1
H H13A 0.207363 0.629185 0.229242 0.093 Uiso calc U P R 0.665(6) A 1
H H13B 0.207687 0.553746 0.376285 0.093 Uiso calc U P R 0.665(6) A 1
C C14 0.0140(6) 0.5662(10) 0.2928(7) 0.113(2) Uani d . P D 0.665(6) A 1
H H14A -0.05645 0.672992 0.283915 0.136 Uiso calc U P R 0.665(6) A 1
H H14B -0.010428 0.493723 0.370269 0.136 Uiso calc U P R 0.665(6) A 1
C C15 -0.0206(10) 0.5361(14) 0.1839(9) 0.140(4) Uani d . P D 0.665(6) A 1
H H15A -0.009675 0.616594 0.105578 0.168 Uiso calc U P R 0.665(6) A 1
H H15B -0.131252 0.541898 0.186264 0.168 Uiso calc U P R 0.665(6) A 1
C C16 0.0973(9) 0.3737(11) 0.1907(9) 0.120(2) Uani d . P D 0.665(6) A 1
H H16A 0.078547 0.292816 0.264938 0.144 Uiso calc U P R 0.665(6) A 1
H H16B 0.078446 0.357909 0.117892 0.144 Uiso calc U P R 0.665(6) A 1
C C17 0.2657(6) 0.3585(6) 0.1952(5) 0.0887(14) Uani d . P D 0.665(6) A 1
H H17A 0.287778 0.431401 0.116767 0.106 Uiso calc U P R 0.665(6) A 1
H H17B 0.338669 0.252065 0.205045 0.106 Uiso calc U P R 0.665(6) A 1
N N3A 0.2310(14) 0.3622(9) 0.3501(9) 0.092(3) Uani d . P D 0.335(6) A 2
C C13A 0.1113(12) 0.5010(10) 0.3661(8) 0.085(3) Uani d . P D 0.335(6) A 2
H H13C 0.157466 0.528818 0.419792 0.103 Uiso calc U P R 0.335(6) A 2
H H13D 0.018288 0.478165 0.40648 0.103 Uiso calc U P R 0.335(6) A 2
C C14A 0.0570(14) 0.6379(10) 0.2417(9) 0.091(3) Uani d . P D 0.335(6) A 2
H H14C -0.031776 0.725418 0.254108 0.109 Uiso calc U P R 0.335(6) A 2
H H14D 0.1461 0.671942 0.208632 0.109 Uiso calc U P R 0.335(6) A 2
C C15A 0.0025(17) 0.5983(16) 0.1474(12) 0.104(5) Uani d . P D 0.335(6) A 2
H H15C -0.01305 0.683785 0.065635 0.125 Uiso calc U P R 0.335(6) A 2
H H15D -0.101026 0.587874 0.170548 0.125 Uiso calc U P R 0.335(6) A 2
C C16A 0.1260(17) 0.4455(13) 0.1400(9) 0.099(3) Uani d . P D 0.335(6) A 2
H H16C 0.079247 0.414737 0.08893 0.119 Uiso calc U P R 0.335(6) A 2
H H16D 0.22067 0.46397 0.0989 0.119 Uiso calc U P R 0.335(6) A 2
C C17A 0.1777(18) 0.3144(11) 0.2642(10) 0.109(4) Uani d . P D 0.335(6) A 2
H H17C 0.087961 0.28231 0.29931 0.131 Uiso calc U P R 0.335(6) A 2
H H17D 0.26623 0.224525 0.254816 0.131 Uiso calc U P R 0.335(6) 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.215(3) ?
O2 C3 . 1.223(3) ?
O3 C9 . 1.385(3) ?
O3 C12 . 1.386(4) ?
N1 C3 . 1.346(3) ?
N1 N2 . 1.411(2) ?
N1 C2 . 1.441(3) ?
N2 C5 . 1.458(3) ?
N2 H2 . 0.90(3) ?
C1 N3 . 1.313(4) ?
C1 C2 . 1.526(3) ?
C1 N3A . 1.554(11) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C3 C4 . 1.490(4) ?
C4 H4A . 0.96 ?
C4 H4B . 0.96 ?
C4 H4C . 0.96 ?
C5 C6 . 1.503(3) ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
C6 C7 . 1.366(4) ?
C6 C11 . 1.393(3) ?
C7 C8 . 1.404(4) ?
C7 H7 . 0.93 ?
C8 C9 . 1.399(4) ?
C8 H8 . 0.93 ?
C9 C10 . 1.342(4) ?
C10 C11 . 1.361(4) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?
N3 C13 . 1.460(5) ?
N3 C17 . 1.467(5) ?
C13 C14 . 1.494(6) ?
C13 H13A . 0.97 ?
C13 H13B . 0.97 ?
C14 C15 . 1.512(9) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 C16 . 1.521(10) ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C16 C17 . 1.465(7) ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
N3A C13A . 1.445(11) ?
N3A C17A . 1.467(10) ?
C13A C14A . 1.503(11) ?
C13A H13C . 0.97 ?
C13A H13D . 0.97 ?
C14A C15A . 1.500(13) ?
C14A H14C . 0.97 ?
C14A H14D . 0.97 ?
C15A C16A . 1.518(14) ?
C15A H15C . 0.97 ?
C15A H15D . 0.97 ?
C16A C17A . 1.478(12) ?
C16A H16C . 0.97 ?
C16A H16D . 0.97 ?
C17A H17C . 0.97 ?
C17A H17D . 0.97 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O3 C12 . . 119.0(3) ?
C3 N1 N2 . . 119.03(18) ?
C3 N1 C2 . . 120.19(19) ?
N2 N1 C2 . . 119.55(18) ?
N1 N2 C5 . . 113.44(18) ?
N1 N2 H2 . . 110.1(17) ?
C5 N2 H2 . . 108.4(17) ?
O1 C1 N3 . . 121.9(2) ?
O1 C1 C2 . . 120.8(2) ?
N3 C1 C2 . . 116.4(2) ?
O1 C1 N3A . . 123.0(3) ?
C2 C1 N3A . . 111.2(4) ?
N1 C2 C1 . . 111.22(18) ?
N1 C2 H2A . . 109.4 ?
C1 C2 H2A . . 109.4 ?
N1 C2 H2B . . 109.4 ?
C1 C2 H2B . . 109.4 ?
H2A C2 H2B . . 108.0 ?
O2 C3 N1 . . 121.4(2) ?
O2 C3 C4 . . 121.3(2) ?
N1 C3 C4 . . 117.3(2) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N2 C5 C6 . . 112.93(19) ?
N2 C5 H5A . . 109.0 ?
C6 C5 H5A . . 109.0 ?
N2 C5 H5B . . 109.0 ?
C6 C5 H5B . . 109.0 ?
H5A C5 H5B . . 107.8 ?
C7 C6 C11 . . 119.0(2) ?
C7 C6 C5 . . 121.6(2) ?
C11 C6 C5 . . 119.4(2) ?
C6 C7 C8 . . 120.2(2) ?
C6 C7 H7 . . 119.9 ?
C8 C7 H7 . . 119.9 ?
C9 C8 C7 . . 118.3(2) ?
C9 C8 H8 . . 120.9 ?
C7 C8 H8 . . 120.9 ?
C10 C9 O3 . . 116.5(2) ?
C10 C9 C8 . . 121.3(2) ?
O3 C9 C8 . . 122.2(2) ?
C9 C10 C11 . . 119.9(2) ?
C9 C10 H10 . . 120.1 ?
C11 C10 H10 . . 120.1 ?
C10 C11 C6 . . 121.4(2) ?
C10 C11 H11 . . 119.3 ?
C6 C11 H11 . . 119.3 ?
O3 C12 H12A . . 109.5 ?
O3 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
O3 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C1 N3 C13 . . 124.7(3) ?
C1 N3 C17 . . 120.2(3) ?
C13 N3 C17 . . 115.0(3) ?
N3 C13 C14 . . 110.3(4) ?
N3 C13 H13A . . 109.6 ?
C14 C13 H13A . . 109.6 ?
N3 C13 H13B . . 109.6 ?
C14 C13 H13B . . 109.6 ?
H13A C13 H13B . . 108.1 ?
C13 C14 C15 . . 112.1(5) ?
C13 C14 H14A . . 109.2 ?
C15 C14 H14A . . 109.2 ?
C13 C14 H14B . . 109.2 ?
C15 C14 H14B . . 109.2 ?
H14A C14 H14B . . 107.9 ?
C14 C15 C16 . . 110.1(7) ?
C14 C15 H15A . . 109.6 ?
C16 C15 H15A . . 109.6 ?
C14 C15 H15B . . 109.6 ?
C16 C15 H15B . . 109.6 ?
H15A C15 H15B . . 108.2 ?
C17 C16 C15 . . 110.7(5) ?
C17 C16 H16A . . 109.5 ?
C15 C16 H16A . . 109.5 ?
C17 C16 H16B . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 108.1 ?
C16 C17 N3 . . 111.2(5) ?
C16 C17 H17A . . 109.4 ?
N3 C17 H17A . . 109.4 ?
C16 C17 H17B . . 109.4 ?
N3 C17 H17B . . 109.4 ?
H17A C17 H17B . . 108.0 ?
C13A N3A C17A . . 114.3(8) ?
C13A N3A C1 . . 127.2(6) ?
C17A N3A C1 . . 116.1(9) ?
N3A C13A C14A . . 110.8(7) ?
N3A C13A H13C . . 109.5 ?
C14A C13A H13C . . 109.5 ?
N3A C13A H13D . . 109.5 ?
C14A C13A H13D . . 109.5 ?
H13C C13A H13D . . 108.1 ?
C15A C14A C13A . . 113.0(9) ?
C15A C14A H14C . . 109.0 ?
C13A C14A H14C . . 109.0 ?
C15A C14A H14D . . 109.0 ?
C13A C14A H14D . . 109.0 ?
H14C C14A H14D . . 107.8 ?
C14A C15A C16A . . 111.3(9) ?
C14A C15A H15C . . 109.4 ?
C16A C15A H15C . . 109.4 ?
C14A C15A H15D . . 109.4 ?
C16A C15A H15D . . 109.4 ?
H15C C15A H15D . . 108.0 ?
C17A C16A C15A . . 113.1(10) ?
C17A C16A H16C . . 109.0 ?
C15A C16A H16C . . 109.0 ?
C17A C16A H16D . . 109.0 ?
C15A C16A H16D . . 109.0 ?
H16C C16A H16D . . 107.8 ?
N3A C17A C16A . . 111.0(8) ?
N3A C17A H17C . . 109.4 ?
C16A C17A H17C . . 109.4 ?
N3A C17A H17D . . 109.4 ?
C16A C17A H17D . . 109.4 ?
H17C C17A H17D . . 108.0 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 N2 C5 . . . . 127.4(2) ?
C2 N1 N2 C5 . . . . -65.2(2) ?
C3 N1 C2 C1 . . . . 98.8(2) ?
N2 N1 C2 C1 . . . . -68.4(3) ?
O1 C1 C2 N1 . . . . -4.8(4) ?
N3 C1 C2 N1 . . . . -174.0(3) ?
N3A C1 C2 N1 . . . . 150.9(5) ?
N2 N1 C3 O2 . . . . 171.91(19) ?
C2 N1 C3 O2 . . . . 4.6(3) ?
N2 N1 C3 C4 . . . . -10.8(3) ?
C2 N1 C3 C4 . . . . -178.04(19) ?
N1 N2 C5 C6 . . . . -71.8(3) ?
N2 C5 C6 C7 . . . . -73.7(3) ?
N2 C5 C6 C11 . . . . 107.7(3) ?
C11 C6 C7 C8 . . . . 1.5(4) ?
C5 C6 C7 C8 . . . . -177.0(2) ?
C6 C7 C8 C9 . . . . -0.1(4) ?
C12 O3 C9 C10 . . . . 175.7(3) ?
C12 O3 C9 C8 . . . . -6.3(4) ?
C7 C8 C9 C10 . . . . -1.6(4) ?
C7 C8 C9 O3 . . . . -179.4(2) ?
O3 C9 C10 C11 . . . . 179.7(2) ?
C8 C9 C10 C11 . . . . 1.7(4) ?
C9 C10 C11 C6 . . . . -0.2(4) ?
C7 C6 C11 C10 . . . . -1.4(4) ?
C5 C6 C11 C10 . . . . 177.2(2) ?
O1 C1 N3 C13 . . . . -177.1(4) ?
C2 C1 N3 C13 . . . . -8.0(6) ?
O1 C1 N3 C17 . . . . 0.9(6) ?
C2 C1 N3 C17 . . . . 170.0(4) ?
C1 N3 C13 C14 . . . . -128.7(6) ?
C17 N3 C13 C14 . . . . 53.2(6) ?
N3 C13 C14 C15 . . . . -52.6(8) ?
C13 C14 C15 C16 . . . . 54.6(9) ?
C14 C15 C16 C17 . . . . -55.8(10) ?
C15 C16 C17 N3 . . . . 55.3(9) ?
C1 N3 C17 C16 . . . . 126.3(7) ?
C13 N3 C17 C16 . . . . -55.5(7) ?
O1 C1 N3A C13A . . . . 174.6(7) ?
C2 C1 N3A C13A . . . . 19.5(11) ?
O1 C1 N3A C17A . . . . -24.0(10) ?
C2 C1 N3A C17A . . . . -179.1(7) ?
C17A N3A C13A C14A . . . . -55.7(13) ?
C1 N3A C13A C14A . . . . 106.0(12) ?
N3A C13A C14A C15A . . . . 52.2(14) ?
C13A C14A C15A C16A . . . . -49.2(16) ?
C14A C15A C16A C17A . . . . 49.4(17) ?
C13A N3A C17A C16A . . . . 55.9(15) ?
C1 N3A C17A C16A . . . . -107.9(13) ?
C15A C16A C17A N3A . . . . -51.8(17) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2 O1 . 0.90(3) 2.47(3) 3.002(2) 118.(2) ?
N2 H2 O1 2_656 0.90(3) 2.28(3) 3.077(2) 148.(2) ?



####################################################################### 
# 
# 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_rds834
_database_code_depnum_ccdc_archive 'CCDC 2061176'
loop_
_audit_author_name
_audit_author_address
'Roger Sommer'
;North Carolina State University
United States of America
;
_audit_update_record             
;
2021-02-04 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            CD-1-120
_chemical_formula_moiety         'C16 H23 N3 O2'
_chemical_formula_sum            'C16 H23 N3 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         289.37
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.0726(3)
_cell_length_b                   9.9182(5)
_cell_length_c                   26.1540(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.3620(15)
_cell_angle_gamma                90
_cell_volume                     1572.53(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    217
_cell_measurement_theta_min      3.9864
_cell_measurement_theta_max      25.7871
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.096
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624

_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
 --------------------------------------------------------------------------
 Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.

;
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            27709
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         30.58
_diffrn_reflns_theta_full        30.58
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       36

_refine_special_details          
;
;

_reflns_number_total             9683
_reflns_number_gt                8040
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0882
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_number_reflns         9683
_refine_ls_number_parameters     389
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+0.1202P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.196
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Absolute structuere determination incocnlusive. Light atom structure, molybdenum source.
Flack x determined using 3174 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)

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'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'APEX3 v2018.1-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.0710(2) 0.56699(14) 0.57168(5) 0.0191(3) Uani d . . . 1 . .
O O2 0.2529(2) 0.78392(13) 0.48480(5) 0.0194(3) Uani d . . . 1 . .
N N1 0.2284(3) 0.55767(15) 0.47915(6) 0.0148(3) Uani d . . . 1 . .
N N2 0.0950(3) 0.44713(15) 0.46270(6) 0.0164(3) Uani d . . . 1 . .
H H2 0.028(4) 0.413(2) 0.4885(8) 0.020(6) Uiso d . . . 1 . .
N N3 0.3973(3) 0.54085(17) 0.61664(6) 0.0186(3) Uani d . . . 1 . .
C C1 0.2721(3) 0.55058(18) 0.57252(7) 0.0145(3) Uani d . . . 1 . .
C C2 0.3877(3) 0.54023(19) 0.52237(7) 0.0147(4) Uani d . . . 1 . .
H H2A 0.50326 0.610469 0.521409 0.018 Uiso calc U . R 1 . .
H H2B 0.459656 0.451006 0.520166 0.018 Uiso calc U . R 1 . .
C C3 0.1579(3) 0.68362(18) 0.46647(7) 0.0145(3) Uani d . . . 1 . .
C C4 -0.0399(3) 0.6954(2) 0.42930(8) 0.0207(4) Uani d . . . 1 . .
H H4A -0.016593 0.640679 0.398893 0.031 Uiso calc U . R 1 . .
H H4B -0.060656 0.789908 0.419204 0.031 Uiso calc U . R 1 . .
H H4C -0.171381 0.663267 0.445607 0.031 Uiso calc U . R 1 . .
C C5 0.2246(3) 0.34180(19) 0.43897(8) 0.0194(4) Uani d . . . 1 . .
H H5A 0.139086 0.256801 0.43691 0.023 Uiso calc U . R 1 . .
H H5B 0.362214 0.325204 0.460239 0.023 Uiso calc U . R 1 . .
C C6 0.2801(3) 0.38484(19) 0.38609(7) 0.0188(4) Uani d . . . 1 . .
C C7 0.1179(3) 0.3827(2) 0.34624(8) 0.0227(4) Uani d . . . 1 . .
H H7 -0.024865 0.34934 0.352295 0.027 Uiso calc U . R 1 . .
C C8 0.1619(4) 0.4286(2) 0.29783(8) 0.0270(5) Uani d . . . 1 . .
H H8 0.049324 0.426745 0.271039 0.032 Uiso calc U . R 1 . .
C C9 0.3693(4) 0.4771(2) 0.28842(8) 0.0285(5) Uani d . . . 1 . .
H H9 0.399426 0.508794 0.255268 0.034 Uiso calc U . R 1 . .
C C10 0.5322(4) 0.4793(2) 0.32753(9) 0.0299(5) Uani d . . . 1 . .
H H10 0.674802 0.51245 0.321223 0.036 Uiso calc U . R 1 . .
C C11 0.4885(3) 0.4330(2) 0.37618(8) 0.0251(4) Uani d . . . 1 . .
H H11 0.601838 0.434334 0.4028 0.03 Uiso calc U . R 1 . .
C C12 0.6322(3) 0.5067(2) 0.62057(8) 0.0205(4) Uani d . . . 1 . .
H H12A 0.716066 0.579558 0.638803 0.025 Uiso calc U . R 1 . .
H H12B 0.687456 0.498187 0.58585 0.025 Uiso calc U . R 1 . .
C C13 0.6673(3) 0.3746(2) 0.64943(7) 0.0218(4) Uani d . . . 1 . .
H H13A 0.827412 0.356242 0.654374 0.026 Uiso calc U . R 1 . .
H H13B 0.599265 0.30012 0.628871 0.026 Uiso calc U . R 1 . .
C C14 0.5665(3) 0.3795(2) 0.70146(8) 0.0232(4) Uani d . . . 1 . .
H H14A 0.578978 0.289687 0.717859 0.028 Uiso calc U . R 1 . .
H H14B 0.649004 0.444909 0.723864 0.028 Uiso calc U . R 1 . .
C C15 0.3247(3) 0.4208(2) 0.69572(8) 0.0246(4) Uani d . . . 1 . .
H H15A 0.238495 0.348835 0.67759 0.029 Uiso calc U . R 1 . .
H H15B 0.26677 0.432129 0.730057 0.029 Uiso calc U . R 1 . .
C C16 0.2971(3) 0.5522(2) 0.66595(7) 0.0236(4) Uani d . . . 1 . .
H H16A 0.138216 0.573249 0.660233 0.028 Uiso calc U . R 1 . .
H H16B 0.367837 0.62663 0.686051 0.028 Uiso calc U . R 1 . .
O O3 0.5375(2) 0.79434(14) 0.93000(5) 0.0186(3) Uani d . . . 1 . .
O O4 0.7616(2) 1.00851(13) 1.01447(5) 0.0196(3) Uani d . . . 1 . .
N N4 0.7415(3) 0.78274(15) 1.02233(6) 0.0140(3) Uani d . . . 1 . .
N N5 0.6169(3) 0.67316(16) 1.03983(6) 0.0162(3) Uani d . . . 1 . .
H H5 0.532(4) 0.639(2) 1.0141(8) 0.021(6) Uiso d . . . 1 . .
N N6 0.8403(3) 0.76580(18) 0.88498(6) 0.0183(3) Uani d . . . 1 . .
C C17 0.7370(3) 0.77588(18) 0.92896(7) 0.0138(3) Uani d . . . 1 . .
C C18 0.8781(3) 0.76276(18) 0.97928(7) 0.0142(4) Uani d . . . 1 . .
H H18A 0.946595 0.6722 0.981427 0.017 Uiso calc U . R 1 . .
H H18B 0.99759 0.830804 0.980311 0.017 Uiso calc U . R 1 . .
C C19 0.6775(3) 0.90969(18) 1.03412(7) 0.0149(4) Uani d . . . 1 . .
C C20 0.5003(3) 0.9237(2) 1.07158(8) 0.0214(4) Uani d . . . 1 . .
H H20A 0.359684 0.891741 1.055718 0.032 Uiso calc U . R 1 . .
H H20B 0.486252 1.018691 1.081227 0.032 Uiso calc U . R 1 . .
H H20C 0.539483 0.869945 1.1022 0.032 Uiso calc U . R 1 . .
C C21 0.7591(3) 0.56845(19) 1.06389(7) 0.0190(4) Uani d . . . 1 . .
H H21A 0.882648 0.548967 1.041934 0.023 Uiso calc U . R 1 . .
H H21B 0.673319 0.484454 1.067468 0.023 Uiso calc U . R 1 . .
C C22 0.8490(3) 0.61474(19) 1.11585(7) 0.0178(4) Uani d . . . 1 . .
C C23 1.0609(3) 0.6672(2) 1.12316(8) 0.0239(4) Uani d . . . 1 . .
H H23 1.155127 0.668615 1.095428 0.029 Uiso calc U . R 1 . .
C C24 1.1364(4) 0.7175(2) 1.17070(9) 0.0290(5) Uani d . . . 1 . .
H H24 1.280752 0.754263 1.175078 0.035 Uiso calc U . R 1 . .
C C25 1.0019(4) 0.7143(2) 1.21155(8) 0.0269(5) Uani d . . . 1 . .
H H25 1.053496 0.748353 1.244025 0.032 Uiso calc U . R 1 . .
C C26 0.7914(4) 0.6609(2) 1.20479(8) 0.0273(5) Uani d . . . 1 . .
H H26 0.698479 0.658139 1.232746 0.033 Uiso calc U . R 1 . .
C C27 0.7160(3) 0.6116(2) 1.15734(8) 0.0219(4) Uani d . . . 1 . .
H H27 0.571394 0.575083 1.153122 0.026 Uiso calc U . R 1 . .
C C28 0.7185(3) 0.7879(2) 0.83588(7) 0.0221(4) Uani d . . . 1 . .
H H28A 0.780461 0.866953 0.818631 0.027 Uiso calc U . R 1 . .
H H28B 0.562162 0.807339 0.841775 0.027 Uiso calc U . R 1 . .
C C29 0.7318(3) 0.6647(2) 0.80158(8) 0.0260(4) Uani d . . . 1 . .
H H29A 0.65899 0.68464 0.767555 0.031 Uiso calc U . R 1 . .
H H29B 0.652756 0.588531 0.816705 0.031 Uiso calc U . R 1 . .
C C30 0.9713(4) 0.6251(2) 0.79535(8) 0.0272(5) Uani d . . . 1 . .
H H30A 1.044531 0.695728 0.775677 0.033 Uiso calc U . R 1 . .
H H30B 0.976273 0.539654 0.775891 0.033 Uiso calc U . R 1 . .
C C31 1.0942(3) 0.6076(2) 0.84750(8) 0.0242(4) Uani d . . . 1 . .
H H31A 1.033812 0.528622 0.865114 0.029 Uiso calc U . R 1 . .
H H31B 1.252031 0.590005 0.842597 0.029 Uiso calc U . R 1 . .
C C32 1.0733(3) 0.7322(2) 0.88078(7) 0.0190(4) Uani d . . . 1 . .
H H32A 1.14347 0.715107 0.915297 0.023 Uiso calc U . R 1 . .
H H32B 1.150323 0.808989 0.865496 0.023 Uiso calc U . R 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.231(2) ?
O2 C3 . 1.233(2) ?
N1 C3 . 1.356(2) ?
N1 N2 . 1.415(2) ?
N1 C2 . 1.454(2) ?
N2 C5 . 1.467(3) ?
N2 H2 . 0.88(2) ?
N3 C1 . 1.348(2) ?
N3 C16 . 1.462(2) ?
N3 C12 . 1.464(2) ?
C1 C2 . 1.527(2) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.505(3) ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 C6 . 1.504(3) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C11 . 1.391(3) ?
C6 C7 . 1.391(3) ?
C7 C8 . 1.386(3) ?
C7 H7 . 0.95 ?
C8 C9 . 1.384(3) ?
C8 H8 . 0.95 ?
C9 C10 . 1.381(3) ?
C9 H9 . 0.95 ?
C10 C11 . 1.393(3) ?
C10 H10 . 0.95 ?
C11 H11 . 0.95 ?
C12 C13 . 1.521(3) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.525(3) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.523(3) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.522(3) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
O3 C17 . 1.227(2) ?
O4 C19 . 1.231(2) ?
N4 C19 . 1.358(2) ?
N4 N5 . 1.415(2) ?
N4 C18 . 1.451(2) ?
N5 C21 . 1.468(3) ?
N5 H5 . 0.89(2) ?
N6 C17 . 1.346(2) ?
N6 C28 . 1.460(2) ?
N6 C32 . 1.464(2) ?
C17 C18 . 1.533(3) ?
C18 H18A . 0.99 ?
C18 H18B . 0.99 ?
C19 C20 . 1.504(3) ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
C21 C22 . 1.506(3) ?
C21 H21A . 0.99 ?
C21 H21B . 0.99 ?
C22 C23 . 1.390(3) ?
C22 C27 . 1.391(3) ?
C23 C24 . 1.392(3) ?
C23 H23 . 0.95 ?
C24 C25 . 1.383(3) ?
C24 H24 . 0.95 ?
C25 C26 . 1.385(3) ?
C25 H25 . 0.95 ?
C26 C27 . 1.387(3) ?
C26 H26 . 0.95 ?
C27 H27 . 0.95 ?
C28 C29 . 1.520(3) ?
C28 H28A . 0.99 ?
C28 H28B . 0.99 ?
C29 C30 . 1.524(3) ?
C29 H29A . 0.99 ?
C29 H29B . 0.99 ?
C30 C31 . 1.526(3) ?
C30 H30A . 0.99 ?
C30 H30B . 0.99 ?
C31 C32 . 1.521(3) ?
C31 H31A . 0.99 ?
C31 H31B . 0.99 ?
C32 H32A . 0.99 ?
C32 H32B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 N1 N2 . . 118.20(15) ?
C3 N1 C2 . . 119.08(15) ?
N2 N1 C2 . . 119.14(14) ?
N1 N2 C5 . . 111.63(15) ?
N1 N2 H2 . . 110.4(15) ?
C5 N2 H2 . . 109.5(14) ?
C1 N3 C16 . . 120.43(16) ?
C1 N3 C12 . . 125.11(16) ?
C16 N3 C12 . . 114.21(15) ?
O1 C1 N3 . . 122.28(17) ?
O1 C1 C2 . . 119.95(16) ?
N3 C1 C2 . . 117.77(15) ?
N1 C2 C1 . . 109.95(14) ?
N1 C2 H2A . . 109.7 ?
C1 C2 H2A . . 109.7 ?
N1 C2 H2B . . 109.7 ?
C1 C2 H2B . . 109.7 ?
H2A C2 H2B . . 108.2 ?
O2 C3 N1 . . 120.97(17) ?
O2 C3 C4 . . 121.75(17) ?
N1 C3 C4 . . 117.29(16) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N2 C5 C6 . . 109.95(16) ?
N2 C5 H5A . . 109.7 ?
C6 C5 H5A . . 109.7 ?
N2 C5 H5B . . 109.7 ?
C6 C5 H5B . . 109.7 ?
H5A C5 H5B . . 108.2 ?
C11 C6 C7 . . 118.51(18) ?
C11 C6 C5 . . 121.59(18) ?
C7 C6 C5 . . 119.84(18) ?
C8 C7 C6 . . 120.9(2) ?
C8 C7 H7 . . 119.6 ?
C6 C7 H7 . . 119.6 ?
C9 C8 C7 . . 120.2(2) ?
C9 C8 H8 . . 119.9 ?
C7 C8 H8 . . 119.9 ?
C10 C9 C8 . . 119.6(2) ?
C10 C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C9 C10 C11 . . 120.3(2) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C6 C11 C10 . . 120.5(2) ?
C6 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
N3 C12 C13 . . 109.99(16) ?
N3 C12 H12A . . 109.7 ?
C13 C12 H12A . . 109.7 ?
N3 C12 H12B . . 109.7 ?
C13 C12 H12B . . 109.7 ?
H12A C12 H12B . . 108.2 ?
C12 C13 C14 . . 111.31(17) ?
C12 C13 H13A . . 109.4 ?
C14 C13 H13A . . 109.4 ?
C12 C13 H13B . . 109.4 ?
C14 C13 H13B . . 109.4 ?
H13A C13 H13B . . 108.0 ?
C15 C14 C13 . . 110.83(16) ?
C15 C14 H14A . . 109.5 ?
C13 C14 H14A . . 109.5 ?
C15 C14 H14B . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 108.1 ?
C16 C15 C14 . . 110.94(17) ?
C16 C15 H15A . . 109.5 ?
C14 C15 H15A . . 109.5 ?
C16 C15 H15B . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 108.0 ?
N3 C16 C15 . . 110.27(16) ?
N3 C16 H16A . . 109.6 ?
C15 C16 H16A . . 109.6 ?
N3 C16 H16B . . 109.6 ?
C15 C16 H16B . . 109.6 ?
H16A C16 H16B . . 108.1 ?
C19 N4 N5 . . 118.23(15) ?
C19 N4 C18 . . 119.13(15) ?
N5 N4 C18 . . 119.14(14) ?
N4 N5 C21 . . 111.69(15) ?
N4 N5 H5 . . 110.0(14) ?
C21 N5 H5 . . 111.1(15) ?
C17 N6 C28 . . 120.20(16) ?
C17 N6 C32 . . 125.59(16) ?
C28 N6 C32 . . 114.20(15) ?
O3 C17 N6 . . 122.70(17) ?
O3 C17 C18 . . 119.77(16) ?
N6 C17 C18 . . 117.52(16) ?
N4 C18 C17 . . 109.76(15) ?
N4 C18 H18A . . 109.7 ?
C17 C18 H18A . . 109.7 ?
N4 C18 H18B . . 109.7 ?
C17 C18 H18B . . 109.7 ?
H18A C18 H18B . . 108.2 ?
O4 C19 N4 . . 120.79(16) ?
O4 C19 C20 . . 121.89(16) ?
N4 C19 C20 . . 117.32(16) ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
N5 C21 C22 . . 110.11(15) ?
N5 C21 H21A . . 109.6 ?
C22 C21 H21A . . 109.6 ?
N5 C21 H21B . . 109.6 ?
C22 C21 H21B . . 109.6 ?
H21A C21 H21B . . 108.2 ?
C23 C22 C27 . . 118.46(19) ?
C23 C22 C21 . . 121.43(17) ?
C27 C22 C21 . . 120.05(18) ?
C22 C23 C24 . . 120.70(19) ?
C22 C23 H23 . . 119.7 ?
C24 C23 H23 . . 119.7 ?
C25 C24 C23 . . 120.2(2) ?
C25 C24 H24 . . 119.9 ?
C23 C24 H24 . . 119.9 ?
C24 C25 C26 . . 119.5(2) ?
C24 C25 H25 . . 120.2 ?
C26 C25 H25 . . 120.2 ?
C25 C26 C27 . . 120.22(19) ?
C25 C26 H26 . . 119.9 ?
C27 C26 H26 . . 119.9 ?
C26 C27 C22 . . 120.90(19) ?
C26 C27 H27 . . 119.5 ?
C22 C27 H27 . . 119.5 ?
N6 C28 C29 . . 110.91(17) ?
N6 C28 H28A . . 109.5 ?
C29 C28 H28A . . 109.5 ?
N6 C28 H28B . . 109.5 ?
C29 C28 H28B . . 109.5 ?
H28A C28 H28B . . 108.0 ?
C28 C29 C30 . . 110.73(18) ?
C28 C29 H29A . . 109.5 ?
C30 C29 H29A . . 109.5 ?
C28 C29 H29B . . 109.5 ?
C30 C29 H29B . . 109.5 ?
H29A C29 H29B . . 108.1 ?
C29 C30 C31 . . 110.71(17) ?
C29 C30 H30A . . 109.5 ?
C31 C30 H30A . . 109.5 ?
C29 C30 H30B . . 109.5 ?
C31 C30 H30B . . 109.5 ?
H30A C30 H30B . . 108.1 ?
C32 C31 C30 . . 111.48(18) ?
C32 C31 H31A . . 109.3 ?
C30 C31 H31A . . 109.3 ?
C32 C31 H31B . . 109.3 ?
C30 C31 H31B . . 109.3 ?
H31A C31 H31B . . 108.0 ?
N6 C32 C31 . . 109.94(17) ?
N6 C32 H32A . . 109.7 ?
C31 C32 H32A . . 109.7 ?
N6 C32 H32B . . 109.7 ?
C31 C32 H32B . . 109.7 ?
H32A C32 H32B . . 108.2 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 N2 C5 . . . . 132.00(17) ?
C2 N1 N2 C5 . . . . -69.5(2) ?
C16 N3 C1 O1 . . . . -1.1(3) ?
C12 N3 C1 O1 . . . . 172.92(19) ?
C16 N3 C1 C2 . . . . 179.00(17) ?
C12 N3 C1 C2 . . . . -6.9(3) ?
C3 N1 C2 C1 . . . . 77.9(2) ?
N2 N1 C2 C1 . . . . -80.41(19) ?
O1 C1 C2 N1 . . . . 2.1(2) ?
N3 C1 C2 N1 . . . . -178.00(15) ?
N2 N1 C3 O2 . . . . 171.20(16) ?
C2 N1 C3 O2 . . . . 12.7(2) ?
N2 N1 C3 C4 . . . . -8.8(2) ?
C2 N1 C3 C4 . . . . -167.36(16) ?
N1 N2 C5 C6 . . . . -75.34(19) ?
N2 C5 C6 C11 . . . . 102.4(2) ?
N2 C5 C6 C7 . . . . -74.7(2) ?
C11 C6 C7 C8 . . . . -0.6(3) ?
C5 C6 C7 C8 . . . . 176.56(19) ?
C6 C7 C8 C9 . . . . 0.2(3) ?
C7 C8 C9 C10 . . . . 0.1(4) ?
C8 C9 C10 C11 . . . . 0.0(4) ?
C7 C6 C11 C10 . . . . 0.7(3) ?
C5 C6 C11 C10 . . . . -176.41(19) ?
C9 C10 C11 C6 . . . . -0.4(3) ?
C1 N3 C12 C13 . . . . -116.7(2) ?
C16 N3 C12 C13 . . . . 57.7(2) ?
N3 C12 C13 C14 . . . . -54.4(2) ?
C12 C13 C14 C15 . . . . 53.6(2) ?
C13 C14 C15 C16 . . . . -53.6(2) ?
C1 N3 C16 C15 . . . . 116.7(2) ?
C12 N3 C16 C15 . . . . -58.0(2) ?
C14 C15 C16 N3 . . . . 54.7(2) ?
C19 N4 N5 C21 . . . . -132.43(17) ?
C18 N4 N5 C21 . . . . 68.9(2) ?
C28 N6 C17 O3 . . . . 5.1(3) ?
C32 N6 C17 O3 . . . . -174.34(19) ?
C28 N6 C17 C18 . . . . -175.20(17) ?
C32 N6 C17 C18 . . . . 5.4(3) ?
C19 N4 C18 C17 . . . . -75.8(2) ?
N5 N4 C18 C17 . . . . 82.71(19) ?
O3 C17 C18 N4 . . . . -3.0(2) ?
N6 C17 C18 N4 . . . . 177.23(16) ?
N5 N4 C19 O4 . . . . -170.54(17) ?
C18 N4 C19 O4 . . . . -11.8(3) ?
N5 N4 C19 C20 . . . . 9.1(2) ?
C18 N4 C19 C20 . . . . 167.82(16) ?
N4 N5 C21 C22 . . . . 73.93(19) ?
N5 C21 C22 C23 . . . . -99.4(2) ?
N5 C21 C22 C27 . . . . 77.5(2) ?
C27 C22 C23 C24 . . . . -1.2(3) ?
C21 C22 C23 C24 . . . . 175.82(19) ?
C22 C23 C24 C25 . . . . 0.9(3) ?
C23 C24 C25 C26 . . . . -0.2(4) ?
C24 C25 C26 C27 . . . . -0.2(4) ?
C25 C26 C27 C22 . . . . -0.1(3) ?
C23 C22 C27 C26 . . . . 0.8(3) ?
C21 C22 C27 C26 . . . . -176.3(2) ?
C17 N6 C28 C29 . . . . -122.0(2) ?
C32 N6 C28 C29 . . . . 57.5(2) ?
N6 C28 C29 C30 . . . . -54.4(2) ?
C28 C29 C30 C31 . . . . 53.4(3) ?
C29 C30 C31 C32 . . . . -54.0(2) ?
C17 N6 C32 C31 . . . . 122.4(2) ?
C28 N6 C32 C31 . . . . -57.0(2) ?
C30 C31 C32 N6 . . . . 54.5(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2 O1 . 0.88(2) 2.66(2) 3.100(2) 112.4(17) ?
N2 H2 O2 2_546 0.88(2) 2.28(2) 3.051(2) 147.(2) ?
N5 H5 O4 2_647 0.89(2) 2.29(2) 3.096(2) 149.8(19) ?



####################################################################### 
# 
# 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_rds893
_database_code_depnum_ccdc_archive 'CCDC 2061174'
loop_
_audit_author_name
_audit_author_address
'Roger Sommer'
;North Carolina State University
United States of America
;
_audit_update_record             
;
2021-02-04 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            CD-2-020
_chemical_formula_moiety         'C16 H21 N3 O2'
_chemical_formula_sum            'C16 H21 N3 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         287.36

_chemical_melting_point          ?

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

_cell_length_a                   5.0586(8)
_cell_length_b                   27.489(4)
_cell_length_c                   10.9711(17)
_cell_angle_alpha                90
_cell_angle_beta                 90.664(4)
_cell_angle_gamma                90
_cell_volume                     1525.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    586
_cell_measurement_theta_min      2.0105
_cell_measurement_theta_max      28.4421
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.116
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            30759
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             3001
_reflns_number_gt                2286
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0754
_refine_ls_wR_factor_gt          0.1741
_refine_ls_wR_factor_ref         0.1829
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_restrained_S_all      1.186
_refine_ls_number_reflns         3001
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²+3.3711P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.359
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'APEX3 v2018.7-2 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5848(5) 0.01466(8) 0.66113(19) 0.0240(5) Uani d . . . 1 . .
O O2 0.4478(5) 0.12557(8) 0.48773(19) 0.0262(6) Uani d . . . 1 . .
N N1 0.2563(5) 0.06990(9) 0.6685(2) 0.0182(6) Uani d . . . 1 . .
N N2 0.1522(5) 0.10762(9) 0.7358(2) 0.0187(6) Uani d . . . 1 . .
N N3 0.1326(6) 0.10376(9) 0.3497(2) 0.0220(6) Uani d . . . 1 . .
C C1 0.4681(6) 0.04582(11) 0.7188(3) 0.0189(7) Uani d . . . 1 . .
C C2 0.5417(7) 0.05848(12) 0.8487(3) 0.0230(7) Uani d . . . 1 . .
H H2A 0.706927 0.042002 0.871378 0.034 Uiso calc U . R 1 . .
H H2B 0.400615 0.047897 0.903124 0.034 Uiso calc U . R 1 . .
H H2C 0.565433 0.093744 0.855966 0.034 Uiso calc U . R 1 . .
C C3 0.1693(6) 0.05950(11) 0.5445(2) 0.0168(6) Uani d . . . 1 . .
H H3A -0.026007 0.057259 0.541525 0.02 Uiso calc U . R 1 . .
H H3B 0.242144 0.027788 0.518401 0.02 Uiso calc U . R 1 . .
C C4 0.2608(6) 0.09926(11) 0.4578(3) 0.0174(7) Uani d . . . 1 . .
C C5 -0.0324(6) 0.13375(11) 0.6887(3) 0.0195(7) Uani d . . . 1 . .
H H5 -0.100733 0.126307 0.609826 0.023 Uiso calc U . R 1 . .
C C6 -0.1371(7) 0.17492(11) 0.7565(3) 0.0200(7) Uani d . . . 1 . .
C C7 -0.0222(7) 0.19106(12) 0.8659(3) 0.0274(8) Uani d . . . 1 . .
H H7 0.128278 0.174801 0.898724 0.033 Uiso calc U . R 1 . .
C C8 -0.1269(8) 0.23049(13) 0.9260(3) 0.0334(9) Uani d . . . 1 . .
H H8 -0.049171 0.240852 1.000867 0.04 Uiso calc U . R 1 . .
C C9 -0.3432(8) 0.25519(13) 0.8791(3) 0.0325(9) Uani d . . . 1 . .
H H9 -0.412966 0.282532 0.920829 0.039 Uiso calc U . R 1 . .
C C10 -0.4568(8) 0.23956(12) 0.7706(3) 0.0315(9) Uani d . . . 1 . .
H H10 -0.604933 0.256438 0.737464 0.038 Uiso calc U . R 1 . .
C C11 -0.3569(7) 0.19971(11) 0.7101(3) 0.0237(7) Uani d . . . 1 . .
H H11 -0.438371 0.189067 0.636367 0.028 Uiso calc U . R 1 . .
C C12 -0.0916(7) 0.07427(13) 0.3085(3) 0.0294(8) Uani d . . . 1 . .
H H12A -0.256177 0.093563 0.314468 0.035 Uiso calc U . R 1 . .
H H12B -0.10868 0.045484 0.362029 0.035 Uiso calc U . R 1 . .
C C13 -0.0564(8) 0.05766(13) 0.1779(3) 0.0340(9) Uani d . . . 1 . .
H H13A -0.219272 0.04095 0.149572 0.041 Uiso calc U . R 1 . .
H H13B 0.09089 0.033994 0.174522 0.041 Uiso calc U . R 1 . .
C C14 0.0016(7) 0.09991(14) 0.0933(3) 0.0286(8) Uani d . . . 1 . .
H H14A -0.15319 0.121909 0.089013 0.034 Uiso calc U . R 1 . .
H H14B 0.035812 0.087563 0.010155 0.034 Uiso calc U . R 1 . .
C C15 0.2420(8) 0.12769(17) 0.1405(3) 0.0399(10) Uani d . . . 1 . .
H H15A 0.399908 0.106452 0.137873 0.048 Uiso calc U . R 1 . .
H H15B 0.274405 0.156253 0.087788 0.048 Uiso calc U . R 1 . .
C C16 0.1970(8) 0.14434(13) 0.2699(3) 0.0316(9) Uani d . . . 1 . .
H H16A 0.358283 0.16075 0.301132 0.038 Uiso calc U . R 1 . .
H H16B 0.050585 0.168235 0.270742 0.038 Uiso calc U . R 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.221(4) ?
O2 C4 . 1.233(4) ?
N1 C1 . 1.370(4) ?
N1 N2 . 1.380(3) ?
N1 C3 . 1.454(3) ?
N2 C5 . 1.282(4) ?
N3 C4 . 1.351(4) ?
N3 C16 . 1.457(4) ?
N3 C12 . 1.462(4) ?
C1 C2 . 1.509(4) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C2 H2C . 0.98 ?
C3 C4 . 1.525(4) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C5 C6 . 1.458(4) ?
C5 H5 . 0.95 ?
C6 C11 . 1.395(4) ?
C6 C7 . 1.399(4) ?
C7 C8 . 1.378(5) ?
C7 H7 . 0.95 ?
C8 C9 . 1.382(5) ?
C8 H8 . 0.95 ?
C9 C10 . 1.385(5) ?
C9 H9 . 0.95 ?
C10 C11 . 1.380(5) ?
C10 H10 . 0.95 ?
C11 H11 . 0.95 ?
C12 C13 . 1.516(5) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.517(5) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.522(5) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.512(5) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 N2 . . 116.7(2) ?
C1 N1 C3 . . 120.6(2) ?
N2 N1 C3 . . 122.3(2) ?
C5 N2 N1 . . 119.1(2) ?
C4 N3 C16 . . 119.3(3) ?
C4 N3 C12 . . 125.7(3) ?
C16 N3 C12 . . 114.6(2) ?
O1 C1 N1 . . 120.7(3) ?
O1 C1 C2 . . 122.4(3) ?
N1 C1 C2 . . 116.9(3) ?
C1 C2 H2A . . 109.5 ?
C1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
N1 C3 C4 . . 110.6(2) ?
N1 C3 H3A . . 109.5 ?
C4 C3 H3A . . 109.5 ?
N1 C3 H3B . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
O2 C4 N3 . . 122.7(3) ?
O2 C4 C3 . . 119.5(3) ?
N3 C4 C3 . . 117.9(3) ?
N2 C5 C6 . . 119.8(3) ?
N2 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
C11 C6 C7 . . 118.6(3) ?
C11 C6 C5 . . 119.1(3) ?
C7 C6 C5 . . 122.3(3) ?
C8 C7 C6 . . 120.1(3) ?
C8 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
C7 C8 C9 . . 121.0(3) ?
C7 C8 H8 . . 119.5 ?
C9 C8 H8 . . 119.5 ?
C8 C9 C10 . . 119.1(3) ?
C8 C9 H9 . . 120.4 ?
C10 C9 H9 . . 120.4 ?
C11 C10 C9 . . 120.6(3) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C10 C11 C6 . . 120.5(3) ?
C10 C11 H11 . . 119.8 ?
C6 C11 H11 . . 119.8 ?
N3 C12 C13 . . 111.1(3) ?
N3 C12 H12A . . 109.4 ?
C13 C12 H12A . . 109.4 ?
N3 C12 H12B . . 109.4 ?
C13 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
C12 C13 C14 . . 111.9(3) ?
C12 C13 H13A . . 109.2 ?
C14 C13 H13A . . 109.2 ?
C12 C13 H13B . . 109.2 ?
C14 C13 H13B . . 109.2 ?
H13A C13 H13B . . 107.9 ?
C13 C14 C15 . . 109.6(3) ?
C13 C14 H14A . . 109.8 ?
C15 C14 H14A . . 109.8 ?
C13 C14 H14B . . 109.8 ?
C15 C14 H14B . . 109.8 ?
H14A C14 H14B . . 108.2 ?
C16 C15 C14 . . 110.1(3) ?
C16 C15 H15A . . 109.6 ?
C14 C15 H15A . . 109.6 ?
C16 C15 H15B . . 109.6 ?
C14 C15 H15B . . 109.6 ?
H15A C15 H15B . . 108.2 ?
N3 C16 C15 . . 111.7(3) ?
N3 C16 H16A . . 109.3 ?
C15 C16 H16A . . 109.3 ?
N3 C16 H16B . . 109.3 ?
C15 C16 H16B . . 109.3 ?
H16A C16 H16B . . 107.9 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 C5 . . . . 174.5(3) ?
C3 N1 N2 C5 . . . . 1.8(4) ?
N2 N1 C1 O1 . . . . -174.1(3) ?
C3 N1 C1 O1 . . . . -1.2(5) ?
N2 N1 C1 C2 . . . . 8.0(4) ?
C3 N1 C1 C2 . . . . -179.1(3) ?
C1 N1 C3 C4 . . . . -102.7(3) ?
N2 N1 C3 C4 . . . . 69.8(4) ?
C16 N3 C4 O2 . . . . -6.7(5) ?
C12 N3 C4 O2 . . . . -179.4(3) ?
C16 N3 C4 C3 . . . . 173.9(3) ?
C12 N3 C4 C3 . . . . 1.2(5) ?
N1 C3 C4 O2 . . . . 20.8(4) ?
N1 C3 C4 N3 . . . . -159.8(3) ?
N1 N2 C5 C6 . . . . -177.5(3) ?
N2 C5 C6 C11 . . . . -173.0(3) ?
N2 C5 C6 C7 . . . . 8.1(5) ?
C11 C6 C7 C8 . . . . 0.4(5) ?
C5 C6 C7 C8 . . . . 179.3(3) ?
C6 C7 C8 C9 . . . . -1.0(6) ?
C7 C8 C9 C10 . . . . 0.6(6) ?
C8 C9 C10 C11 . . . . 0.4(6) ?
C9 C10 C11 C6 . . . . -1.0(6) ?
C7 C6 C11 C10 . . . . 0.6(5) ?
C5 C6 C11 C10 . . . . -178.4(3) ?
C4 N3 C12 C13 . . . . -134.6(3) ?
C16 N3 C12 C13 . . . . 52.5(4) ?
N3 C12 C13 C14 . . . . -52.7(4) ?
C12 C13 C14 C15 . . . . 55.5(4) ?
C13 C14 C15 C16 . . . . -56.4(4) ?
C4 N3 C16 C15 . . . . 131.8(3) ?
C12 N3 C16 C15 . . . . -54.7(4) ?
C14 C15 C16 N3 . . . . 55.9(4) ?



####################################################################### 
# 
# 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_1011
_database_code_depnum_ccdc_archive 'CCDC 2061175'
loop_
_audit_author_name
_audit_author_address
'Roger Sommer'
;North Carolina State University
United States of America
;
_audit_update_record             
;
2021-02-04 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H23 N3 O3'
_chemical_formula_sum            'C17 H23 N3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         317.38

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0802(2)
_cell_length_b                   11.6666(5)
_cell_length_c                   14.3550(6)
_cell_angle_alpha                101.7036(13)
_cell_angle_beta                 95.1179(12)
_cell_angle_gamma                98.2498(11)
_cell_volume                     818.32(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    252
_cell_measurement_theta_min      5.5630
_cell_measurement_theta_max      68.7717
_cell_measurement_temperature    120.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.091
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340

_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      120.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            12430
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         70.78
_diffrn_reflns_theta_full        70.78
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.943
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             2982
_reflns_number_gt                2795
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1091
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_number_reflns         2982
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+0.3042P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2019.1.0.1'
_computing_cell_refinement       'APEX3 v2018.7-2 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.13243(18) 0.53466(9) 0.12539(6) 0.0315(2) Uani d . . . 1 . .
O O2 0.0133(2) 0.19638(8) 0.55343(6) 0.0316(2) Uani d . . . 1 . .
N N3 0.7785(2) 0.42900(9) 0.17131(7) 0.0233(2) Uani d . . . 1 . .
N N4 0.6669(2) 0.39847(9) 0.24871(7) 0.0234(2) Uani d . . . 1 . .
C C5 0.4518(2) 0.32241(11) 0.23461(9) 0.0237(3) Uani d . . . 1 . .
H H5 0.369408 0.286816 0.171304 0.028 Uiso calc U . R 1 . .
C C6 0.3335(2) 0.29073(10) 0.31745(8) 0.0227(3) Uani d . . . 1 . .
O O7 0.8483(2) 0.21243(9) 0.07099(7) 0.0409(3) Uani d . . . 1 . .
C C8 0.1018(3) 0.22591(11) 0.47256(9) 0.0241(3) Uani d . . . 1 . .
C C9 0.4511(3) 0.34140(11) 0.41178(9) 0.0264(3) Uani d . . . 1 . .
H H9 0.61138 0.397856 0.423053 0.032 Uiso calc U . R 1 . .
N N10 0.5136(2) 0.20044(9) -0.04690(7) 0.0262(2) Uani d . . . 1 . .
C C11 0.3355(3) 0.30981(11) 0.48818(9) 0.0276(3) Uani d . . . 1 . .
H H11 0.41537 0.345336 0.551798 0.033 Uiso calc U . R 1 . .
C C12 -0.0212(3) 0.17753(11) 0.37997(9) 0.0254(3) Uani d . . . 1 . .
H H12 -0.183408 0.122285 0.369024 0.03 Uiso calc U . R 1 . .
C C13 1.0168(2) 0.50653(11) 0.19063(9) 0.0242(3) Uani d . . . 1 . .
C C14 0.6483(2) 0.38645(11) 0.07370(8) 0.0233(3) Uani d . . . 1 . .
H H14A 0.727651 0.437598 0.032732 0.028 Uiso calc U . R 1 . .
H H14B 0.455604 0.392383 0.072279 0.028 Uiso calc U . R 1 . .
C C15 0.0954(3) 0.21068(11) 0.30309(9) 0.0253(3) Uani d . . . 1 . .
H H15 0.010408 0.17795 0.239669 0.03 Uiso calc U . R 1 . .
C C16 0.5292(3) 0.07861(12) -0.09268(10) 0.0340(3) Uani d . . . 1 . .
H H16A 0.368472 0.025241 -0.083279 0.041 Uiso calc U . R 1 . .
H H16B 0.688791 0.054441 -0.062275 0.041 Uiso calc U . R 1 . .
C C18 0.6776(2) 0.25757(11) 0.03299(8) 0.0230(3) Uani d . . . 1 . .
C C19 1.1231(3) 0.55653(12) 0.29454(9) 0.0286(3) Uani d . . . 1 . .
H H19A 1.302833 0.602506 0.299157 0.043 Uiso calc U . R 1 . .
H H19B 1.131783 0.491384 0.327778 0.043 Uiso calc U . R 1 . .
H H19C 1.003685 0.608234 0.324266 0.043 Uiso calc U . R 1 . .
C C20 0.2913(4) 0.24653(15) -0.09104(12) 0.0499(5) Uani d . . . 1 . .
H H20A 0.298759 0.330911 -0.059624 0.06 Uiso calc U . R 1 . .
H H20B 0.119031 0.201734 -0.081134 0.06 Uiso calc U . R 1 . .
C C21 0.3039(4) 0.23596(14) -0.19676(13) 0.0500(5) Uani d . . . 1 . .
H H21A 0.464632 0.289165 -0.206341 0.06 Uiso calc U . R 1 . .
H H21B 0.144096 0.261821 -0.225391 0.06 Uiso calc U . R 1 . .
C C22 0.3152(3) 0.11057(14) -0.24701(9) 0.0322(3) Uani d . . . 1 . .
H H22A 0.339257 0.107864 -0.315065 0.039 Uiso calc U . R 1 . .
H H22B 0.144714 0.058634 -0.244863 0.039 Uiso calc U . R 1 . .
C C23 0.5468(3) 0.06615(18) -0.19865(11) 0.0495(5) Uani d . . . 1 . .
H H23A 0.544232 -0.018297 -0.228758 0.059 Uiso calc U . R 1 . .
H H23B 0.718372 0.112027 -0.208014 0.059 Uiso calc U . R 1 . .
C C1 -0.2227(3) 0.11033(13) 0.54191(10) 0.0333(3) Uani d . . . 1 . .
H H1A -0.197483 0.036628 0.499423 0.05 Uiso calc U . R 1 . .
H H1B -0.374625 0.140349 0.513824 0.05 Uiso calc U . R 1 . .
H H1C -0.258469 0.094741 0.604536 0.05 Uiso calc U . R 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C13 . 1.2238(16) ?
O2 C8 . 1.3708(15) ?
O2 C1 . 1.4228(17) ?
N3 C13 . 1.3727(16) ?
N3 N4 . 1.3777(14) ?
N3 C14 . 1.4510(15) ?
N4 C5 . 1.2775(17) ?
C5 C6 . 1.4676(17) ?
C5 H5 . 0.95 ?
C6 C15 . 1.3897(18) ?
C6 C9 . 1.4034(17) ?
O7 C18 . 1.2208(16) ?
C8 C12 . 1.3863(17) ?
C8 C11 . 1.3959(18) ?
C9 C11 . 1.3784(18) ?
C9 H9 . 0.95 ?
N10 C18 . 1.3467(16) ?
N10 C16 . 1.4564(17) ?
N10 C20 . 1.4666(18) ?
C11 H11 . 0.95 ?
C12 C15 . 1.3936(18) ?
C12 H12 . 0.95 ?
C13 C19 . 1.5065(17) ?
C14 C18 . 1.5322(17) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 H15 . 0.95 ?
C16 C23 . 1.511(2) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 C21 . 1.505(3) ?
C20 H20A . 0.99 ?
C20 H20B . 0.99 ?
C21 C22 . 1.506(2) ?
C21 H21A . 0.99 ?
C21 H21B . 0.99 ?
C22 C23 . 1.520(2) ?
C22 H22A . 0.99 ?
C22 H22B . 0.99 ?
C23 H23A . 0.99 ?
C23 H23B . 0.99 ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 O2 C1 . . 117.84(10) ?
C13 N3 N4 . . 116.87(10) ?
C13 N3 C14 . . 120.58(10) ?
N4 N3 C14 . . 122.49(10) ?
C5 N4 N3 . . 119.48(10) ?
N4 C5 C6 . . 119.15(11) ?
N4 C5 H5 . . 120.4 ?
C6 C5 H5 . . 120.4 ?
C15 C6 C9 . . 118.57(11) ?
C15 C6 C5 . . 119.66(11) ?
C9 C6 C5 . . 121.74(11) ?
O2 C8 C12 . . 124.77(11) ?
O2 C8 C11 . . 115.29(11) ?
C12 C8 C11 . . 119.93(11) ?
C11 C9 C6 . . 120.44(12) ?
C11 C9 H9 . . 119.8 ?
C6 C9 H9 . . 119.8 ?
C18 N10 C16 . . 121.08(11) ?
C18 N10 C20 . . 125.34(11) ?
C16 N10 C20 . . 113.34(10) ?
C9 C11 C8 . . 120.35(11) ?
C9 C11 H11 . . 119.8 ?
C8 C11 H11 . . 119.8 ?
C8 C12 C15 . . 119.38(12) ?
C8 C12 H12 . . 120.3 ?
C15 C12 H12 . . 120.3 ?
O1 C13 N3 . . 120.59(11) ?
O1 C13 C19 . . 122.27(11) ?
N3 C13 C19 . . 117.12(11) ?
N3 C14 C18 . . 111.99(10) ?
N3 C14 H14A . . 109.2 ?
C18 C14 H14A . . 109.2 ?
N3 C14 H14B . . 109.2 ?
C18 C14 H14B . . 109.2 ?
H14A C14 H14B . . 107.9 ?
C6 C15 C12 . . 121.25(11) ?
C6 C15 H15 . . 119.4 ?
C12 C15 H15 . . 119.4 ?
N10 C16 C23 . . 111.09(12) ?
N10 C16 H16A . . 109.4 ?
C23 C16 H16A . . 109.4 ?
N10 C16 H16B . . 109.4 ?
C23 C16 H16B . . 109.4 ?
H16A C16 H16B . . 108.0 ?
O7 C18 N10 . . 123.06(11) ?
O7 C18 C14 . . 120.25(11) ?
N10 C18 C14 . . 116.66(10) ?
C13 C19 H19A . . 109.5 ?
C13 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C13 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
N10 C20 C21 . . 111.20(14) ?
N10 C20 H20A . . 109.4 ?
C21 C20 H20A . . 109.4 ?
N10 C20 H20B . . 109.4 ?
C21 C20 H20B . . 109.4 ?
H20A C20 H20B . . 108.0 ?
C20 C21 C22 . . 111.66(12) ?
C20 C21 H21A . . 109.3 ?
C22 C21 H21A . . 109.3 ?
C20 C21 H21B . . 109.3 ?
C22 C21 H21B . . 109.3 ?
H21A C21 H21B . . 107.9 ?
C21 C22 C23 . . 109.89(12) ?
C21 C22 H22A . . 109.7 ?
C23 C22 H22A . . 109.7 ?
C21 C22 H22B . . 109.7 ?
C23 C22 H22B . . 109.7 ?
H22A C22 H22B . . 108.2 ?
C16 C23 C22 . . 111.17(12) ?
C16 C23 H23A . . 109.4 ?
C22 C23 H23A . . 109.4 ?
C16 C23 H23B . . 109.4 ?
C22 C23 H23B . . 109.4 ?
H23A C23 H23B . . 108.0 ?
O2 C1 H1A . . 109.5 ?
O2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 N3 N4 C5 . . . . -176.77(11) ?
C14 N3 N4 C5 . . . . 5.88(17) ?
N3 N4 C5 C6 . . . . -179.75(10) ?
N4 C5 C6 C15 . . . . 178.15(11) ?
N4 C5 C6 C9 . . . . -0.27(18) ?
C1 O2 C8 C12 . . . . -0.38(18) ?
C1 O2 C8 C11 . . . . -179.37(11) ?
C15 C6 C9 C11 . . . . 1.63(19) ?
C5 C6 C9 C11 . . . . -179.93(12) ?
C6 C9 C11 C8 . . . . 0.8(2) ?
O2 C8 C11 C9 . . . . 176.42(11) ?
C12 C8 C11 C9 . . . . -2.63(19) ?
O2 C8 C12 C15 . . . . -176.94(11) ?
C11 C8 C12 C15 . . . . 2.01(18) ?
N4 N3 C13 O1 . . . . 177.55(11) ?
C14 N3 C13 O1 . . . . -5.05(18) ?
N4 N3 C13 C19 . . . . -3.85(16) ?
C14 N3 C13 C19 . . . . 173.55(11) ?
C13 N3 C14 C18 . . . . 105.49(12) ?
N4 N3 C14 C18 . . . . -77.26(13) ?
C9 C6 C15 C12 . . . . -2.25(18) ?
C5 C6 C15 C12 . . . . 179.28(11) ?
C8 C12 C15 C6 . . . . 0.44(19) ?
C18 N10 C16 C23 . . . . -129.62(13) ?
C20 N10 C16 C23 . . . . 55.73(18) ?
C16 N10 C18 O7 . . . . 0.74(19) ?
C20 N10 C18 O7 . . . . 174.72(15) ?
C16 N10 C18 C14 . . . . 178.57(11) ?
C20 N10 C18 C14 . . . . -7.5(2) ?
N3 C14 C18 O7 . . . . -17.50(16) ?
N3 C14 C18 N10 . . . . 164.60(10) ?
C18 N10 C20 C21 . . . . 130.26(13) ?
C16 N10 C20 C21 . . . . -55.36(18) ?
N10 C20 C21 C22 . . . . 54.56(19) ?
C20 C21 C22 C23 . . . . -54.45(19) ?
N10 C16 C23 C22 . . . . -55.10(18) ?
C21 C22 C23 C16 . . . . 54.60(19) ?



####################################################################### 
# 
# 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_rds999
_database_code_depnum_ccdc_archive 'CCDC 2061177'
loop_
_audit_author_name
_audit_author_address
'Roger Sommer'
;North Carolina State University
United States of America
;
_audit_update_record             
;
2021-02-04 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            BL-1-016
_chemical_formula_moiety         'C17 H22 F3 N3 O2'
_chemical_formula_sum            'C17 H22 F3 N3 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         357.37

_chemical_melting_point          ?

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

_cell_length_a                   6.1398(2)
_cell_length_b                   9.9741(3)
_cell_length_c                   28.5440(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.1500(10)
_cell_angle_gamma                90
_cell_volume                     1740.95(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1092
_cell_measurement_theta_min      3.1008
_cell_measurement_theta_max      50.5945
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.110
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752

_exptl_absorpt_coefficient_mu    0.957
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
(Bruker AXS Inc., 2016)
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            40369
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         77.42
_diffrn_reflns_theta_full        77.42
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_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       -35
_diffrn_reflns_limit_l_max       36

_refine_special_details          
;
;

_reflns_number_total             3695
_reflns_number_gt                3584
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0923
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_number_reflns         3695
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+0.8963P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.435
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
'Bruker Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_structure_solution    'XT, VERSION 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, 2019)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.36962(14) 0.29110(10) 0.00529(3) 0.0429(2) Uani d . . . 1 . .
F F2 0.19380(18) 0.46563(10) 0.02196(3) 0.0564(3) Uani d . . . 1 . .
F F3 0.08718(14) 0.27111(12) 0.04327(3) 0.0514(3) Uani d . . . 1 . .
O O1 1.04805(12) 0.22792(8) 0.32461(3) 0.01987(17) Uani d . . . 1 . .
O O2 0.67065(13) 0.00174(8) 0.23334(3) 0.02235(18) Uani d . . . 1 . .
N N1 0.79150(14) 0.21425(9) 0.24395(3) 0.01609(19) Uani d . . . 1 . .
N N2 0.92536(15) 0.31734(9) 0.22818(3) 0.01744(19) Uani d . . . 1 . .
H H2 1.029(2) 0.3371(14) 0.2514(5) 0.021 Uiso d U . . 1 . .
N N3 0.77689(15) 0.26328(10) 0.37182(3) 0.0218(2) Uani d . . . 1 . .
C C1 0.85213(17) 0.24123(10) 0.32961(4) 0.0162(2) Uani d . . . 1 . .
C C2 0.68295(17) 0.23317(11) 0.28673(4) 0.0171(2) Uani d . . . 1 . .
H H2A 0.581987 0.15744 0.290679 0.021 Uiso calc U . R 1 . .
H H2B 0.595824 0.3168 0.284278 0.021 Uiso calc U . R 1 . .
C C3 0.78046(17) 0.09605(11) 0.22052(4) 0.0165(2) Uani d . . . 1 . .
C C4 0.90945(19) 0.08383(11) 0.17818(4) 0.0216(2) Uani d . . . 1 . .
H H4A 1.063884 0.103002 0.187425 0.032 Uiso calc U . R 1 . .
H H4B 0.853209 0.147983 0.154044 0.032 Uiso calc U . R 1 . .
H H4C 0.895063 -0.007415 0.165546 0.032 Uiso calc U . R 1 . .
C C5 0.79913(19) 0.43868(11) 0.21372(4) 0.0204(2) Uani d . . . 1 . .
H H5A 0.900761 0.513758 0.20931 0.024 Uiso calc U . R 1 . .
H H5B 0.705354 0.464272 0.238732 0.024 Uiso calc U . R 1 . .
C C6 0.65857(18) 0.41376(10) 0.16850(4) 0.0188(2) Uani d . . . 1 . .
C C7 0.44916(19) 0.36047(12) 0.16899(4) 0.0218(2) Uani d . . . 1 . .
H H7 0.392604 0.341622 0.198191 0.026 Uiso calc U . R 1 . .
C C8 0.32184(19) 0.33454(12) 0.12713(4) 0.0236(2) Uani d . . . 1 . .
H H8 0.179473 0.297621 0.127705 0.028 Uiso calc U . R 1 . .
C C9 0.40439(19) 0.36299(12) 0.08459(4) 0.0226(2) Uani d . . . 1 . .
C C10 0.6136(2) 0.41611(13) 0.08347(4) 0.0249(3) Uani d . . . 1 . .
H H10 0.669799 0.435022 0.054244 0.03 Uiso calc U . R 1 . .
C C11 0.73881(19) 0.44111(12) 0.12531(4) 0.0226(2) Uani d . . . 1 . .
H H11 0.881519 0.477435 0.124616 0.027 Uiso calc U . R 1 . .
C C12 0.2644(2) 0.34656(14) 0.03933(5) 0.0307(3) Uani d . . . 1 . .
C C13 0.54777(19) 0.28612(13) 0.38040(4) 0.0253(3) Uani d . . . 1 . .
H H13A 0.498997 0.215342 0.401411 0.03 Uiso calc U . R 1 . .
H H13B 0.454471 0.281813 0.350289 0.03 Uiso calc U . R 1 . .
C C14 0.52413(19) 0.42317(14) 0.40303(5) 0.0278(3) Uani d . . . 1 . .
H H14A 0.371521 0.435096 0.410886 0.033 Uiso calc U . R 1 . .
H H14B 0.556049 0.49409 0.380365 0.033 Uiso calc U . R 1 . .
C C15 0.6791(2) 0.43770(14) 0.44761(4) 0.0286(3) Uani d . . . 1 . .
H H15A 0.635848 0.374324 0.471806 0.034 Uiso calc U . R 1 . .
H H15B 0.66894 0.52981 0.46015 0.034 Uiso calc U . R 1 . .
C C16 0.91466(19) 0.40917(12) 0.43721(4) 0.0234(2) Uani d . . . 1 . .
H H16A 0.964171 0.47928 0.416019 0.028 Uiso calc U . R 1 . .
H H16B 1.011463 0.411673 0.466862 0.028 Uiso calc U . R 1 . .
C C17 0.93051(19) 0.27226(12) 0.41419(4) 0.0231(2) Uani d . . . 1 . .
H H17A 1.081485 0.257745 0.405655 0.028 Uiso calc U . R 1 . .
H H17B 0.896712 0.201393 0.436715 0.028 Uiso calc U . R 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C12 . 1.3341(15) ?
F2 C12 . 1.3437(16) ?
F3 C12 . 1.3362(17) ?
O1 C1 . 1.2312(13) ?
O2 C3 . 1.2319(13) ?
N1 C3 . 1.3542(14) ?
N1 N2 . 1.4149(12) ?
N1 C2 . 1.4550(13) ?
N2 C5 . 1.4758(14) ?
N2 H2 . 0.898(15) ?
N3 C1 . 1.3465(14) ?
N3 C13 . 1.4672(14) ?
N3 C17 . 1.4682(14) ?
C1 C2 . 1.5346(14) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.5082(15) ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 C6 . 1.5077(15) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.3925(16) ?
C6 C11 . 1.3948(16) ?
C7 C8 . 1.3922(16) ?
C7 H7 . 0.95 ?
C8 C9 . 1.3864(17) ?
C8 H8 . 0.95 ?
C9 C10 . 1.3923(17) ?
C9 C12 . 1.4950(16) ?
C10 C11 . 1.3839(17) ?
C10 H10 . 0.95 ?
C11 H11 . 0.95 ?
C13 C14 . 1.5244(18) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.5261(17) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.5288(16) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 C17 . 1.5223(16) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C17 H17A . 0.99 ?
C17 H17B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 N1 N2 . . 118.70(9) ?
C3 N1 C2 . . 121.41(9) ?
N2 N1 C2 . . 119.72(8) ?
N1 N2 C5 . . 112.30(8) ?
N1 N2 H2 . . 108.5(9) ?
C5 N2 H2 . . 110.2(9) ?
C1 N3 C13 . . 125.86(9) ?
C1 N3 C17 . . 120.03(9) ?
C13 N3 C17 . . 114.06(9) ?
O1 C1 N3 . . 122.58(10) ?
O1 C1 C2 . . 120.03(9) ?
N3 C1 C2 . . 117.39(9) ?
N1 C2 C1 . . 110.36(8) ?
N1 C2 H2A . . 109.6 ?
C1 C2 H2A . . 109.6 ?
N1 C2 H2B . . 109.6 ?
C1 C2 H2B . . 109.6 ?
H2A C2 H2B . . 108.1 ?
O2 C3 N1 . . 121.50(10) ?
O2 C3 C4 . . 121.14(10) ?
N1 C3 C4 . . 117.36(9) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N2 C5 C6 . . 110.49(9) ?
N2 C5 H5A . . 109.6 ?
C6 C5 H5A . . 109.6 ?
N2 C5 H5B . . 109.6 ?
C6 C5 H5B . . 109.6 ?
H5A C5 H5B . . 108.1 ?
C7 C6 C11 . . 118.90(10) ?
C7 C6 C5 . . 120.82(10) ?
C11 C6 C5 . . 120.26(10) ?
C8 C7 C6 . . 120.67(11) ?
C8 C7 H7 . . 119.7 ?
C6 C7 H7 . . 119.7 ?
C9 C8 C7 . . 119.50(11) ?
C9 C8 H8 . . 120.3 ?
C7 C8 H8 . . 120.3 ?
C8 C9 C10 . . 120.57(11) ?
C8 C9 C12 . . 120.49(11) ?
C10 C9 C12 . . 118.79(11) ?
C11 C10 C9 . . 119.40(11) ?
C11 C10 H10 . . 120.3 ?
C9 C10 H10 . . 120.3 ?
C10 C11 C6 . . 120.96(11) ?
C10 C11 H11 . . 119.5 ?
C6 C11 H11 . . 119.5 ?
F1 C12 F3 . . 106.20(11) ?
F1 C12 F2 . . 105.02(11) ?
F3 C12 F2 . . 106.89(11) ?
F1 C12 C9 . . 113.36(10) ?
F3 C12 C9 . . 113.47(11) ?
F2 C12 C9 . . 111.30(11) ?
N3 C13 C14 . . 109.83(10) ?
N3 C13 H13A . . 109.7 ?
C14 C13 H13A . . 109.7 ?
N3 C13 H13B . . 109.7 ?
C14 C13 H13B . . 109.7 ?
H13A C13 H13B . . 108.2 ?
C13 C14 C15 . . 111.26(11) ?
C13 C14 H14A . . 109.4 ?
C15 C14 H14A . . 109.4 ?
C13 C14 H14B . . 109.4 ?
C15 C14 H14B . . 109.4 ?
H14A C14 H14B . . 108.0 ?
C14 C15 C16 . . 110.50(9) ?
C14 C15 H15A . . 109.5 ?
C16 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
C16 C15 H15B . . 109.5 ?
H15A C15 H15B . . 108.1 ?
C17 C16 C15 . . 110.43(10) ?
C17 C16 H16A . . 109.6 ?
C15 C16 H16A . . 109.6 ?
C17 C16 H16B . . 109.6 ?
C15 C16 H16B . . 109.6 ?
H16A C16 H16B . . 108.1 ?
N3 C17 C16 . . 110.43(10) ?
N3 C17 H17A . . 109.6 ?
C16 C17 H17A . . 109.6 ?
N3 C17 H17B . . 109.6 ?
C16 C17 H17B . . 109.6 ?
H17A C17 H17B . . 108.1 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 N2 C5 . . . . 118.87(10) ?
C2 N1 N2 C5 . . . . -65.87(12) ?
C13 N3 C1 O1 . . . . 177.09(11) ?
C17 N3 C1 O1 . . . . -0.02(16) ?
C13 N3 C1 C2 . . . . -2.78(16) ?
C17 N3 C1 C2 . . . . -179.90(10) ?
C3 N1 C2 C1 . . . . 108.85(10) ?
N2 N1 C2 C1 . . . . -66.28(12) ?
O1 C1 C2 N1 . . . . -2.07(14) ?
N3 C1 C2 N1 . . . . 177.80(9) ?
N2 N1 C3 O2 . . . . 178.28(9) ?
C2 N1 C3 O2 . . . . 3.11(15) ?
N2 N1 C3 C4 . . . . -1.29(14) ?
C2 N1 C3 C4 . . . . -176.47(9) ?
N1 N2 C5 C6 . . . . -70.85(11) ?
N2 C5 C6 C7 . . . . 87.65(12) ?
N2 C5 C6 C11 . . . . -90.90(12) ?
C11 C6 C7 C8 . . . . 0.15(17) ?
C5 C6 C7 C8 . . . . -178.42(10) ?
C6 C7 C8 C9 . . . . -0.42(18) ?
C7 C8 C9 C10 . . . . 0.51(18) ?
C7 C8 C9 C12 . . . . -175.01(11) ?
C8 C9 C10 C11 . . . . -0.34(18) ?
C12 C9 C10 C11 . . . . 175.26(11) ?
C9 C10 C11 C6 . . . . 0.06(18) ?
C7 C6 C11 C10 . . . . 0.03(17) ?
C5 C6 C11 C10 . . . . 178.61(10) ?
C8 C9 C12 F1 . . . . -138.30(13) ?
C10 C9 C12 F1 . . . . 46.10(17) ?
C8 C9 C12 F3 . . . . -17.04(17) ?
C10 C9 C12 F3 . . . . 167.36(11) ?
C8 C9 C12 F2 . . . . 103.57(14) ?
C10 C9 C12 F2 . . . . -72.03(15) ?
C1 N3 C13 C14 . . . . -119.92(12) ?
C17 N3 C13 C14 . . . . 57.34(13) ?
N3 C13 C14 C15 . . . . -54.86(13) ?
C13 C14 C15 C16 . . . . 54.74(14) ?
C14 C15 C16 C17 . . . . -54.63(14) ?
C1 N3 C17 C16 . . . . 119.41(11) ?
C13 N3 C17 C16 . . . . -58.03(13) ?
C15 C16 C17 N3 . . . . 55.35(13) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2 O1 . 0.898(15) 2.350(14) 2.9271(12) 122.0(11) ?
N2 H2 O2 2_755 0.898(15) 2.479(15) 3.2020(12) 137.8(12) ?



####################################################################### 
# 
# 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_rs003
_database_code_depnum_ccdc_archive 'CCDC 2061173'
loop_
_audit_author_name
_audit_author_address
'Roger Sommer'
;North Carolina State University
United States of America
;
_audit_update_record             
;
2021-02-04 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            BL-1-021
_chemical_formula_moiety         'C17 H20 F3 N3 O2'
_chemical_formula_sum            'C17 H20 F3 N3 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         355.36

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.10660(10)
_cell_length_b                   10.9857(2)
_cell_length_c                   15.6081(3)
_cell_angle_alpha                105.2980(10)
_cell_angle_beta                 96.9290(10)
_cell_angle_gamma                91.0110(10)
_cell_volume                     837.29(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    614
_cell_measurement_theta_min      2.9702
_cell_measurement_theta_max      50.6565
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.033
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372

_exptl_absorpt_coefficient_mu    0.994
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
(Bruker AXS Inc., 2016)
;
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            26360
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         77.41
_diffrn_reflns_theta_full        77.41
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             3472
_reflns_number_gt                3044
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0984
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_number_reflns         3472
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+0.3645P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.279
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
'Bruker Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_structure_solution    'XT, VERSION 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, 2019)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.12771(18) 0.59947(8) 0.22586(6) 0.0276(2) Uani d . . . 1 . .
F F1 1.0677(2) 0.22989(13) 0.58839(7) 0.0634(4) Uani d . . . 1 . .
N N1 0.29848(19) 0.38182(9) 0.12841(7) 0.0191(2) Uani d . . . 1 . .
C C1 0.3014(2) 0.61283(11) 0.18073(8) 0.0189(2) Uani d . . . 1 . .
O O2 -0.07236(17) 0.34957(9) 0.02894(6) 0.0263(2) Uani d . . . 1 . .
F F2 1.4273(2) 0.31792(10) 0.56979(6) 0.0510(3) Uani d . . . 1 . .
N N2 0.43640(19) 0.34054(9) 0.19592(7) 0.0193(2) Uani d . . . 1 . .
C C2 0.3737(2) 0.49864(11) 0.10867(8) 0.0194(2) Uani d . . . 1 . .
H H2A 0.28187 0.500501 0.049454 0.023 Uiso calc U . R 1 . .
H H2AB 0.566298 0.502787 0.106117 0.023 Uiso calc U . R 1 . .
C C9 1.0703(3) 0.28555(13) 0.45291(8) 0.0266(3) Uani d . . . 1 . .
F F3 1.31531(19) 0.12708(9) 0.49624(7) 0.0463(2) Uani d . . . 1 . .
N N3 0.4315(2) 0.72446(10) 0.19070(7) 0.0222(2) Uani d . . . 1 . .
C C3 0.0698(2) 0.31338(11) 0.08508(8) 0.0202(2) Uani d . . . 1 . .
C C4 0.0089(2) 0.19203(12) 0.10819(9) 0.0238(3) Uani d . . . 1 . .
H H4A -0.168119 0.158068 0.079302 0.036 Uiso calc U . R 1 . .
H H4B 0.015734 0.208554 0.17329 0.036 Uiso calc U . R 1 . .
H H4C 0.139326 0.130558 0.087016 0.036 Uiso calc U . R 1 . .
C C5 0.6364(2) 0.40808(11) 0.24358(8) 0.0199(2) Uani d . . . 1 . .
H H5 0.688908 0.485113 0.232178 0.024 Uiso calc U . R 1 . .
C C6 0.7834(2) 0.36477(11) 0.31602(8) 0.0200(2) Uani d . . . 1 . .
C C7 1.0186(2) 0.42924(13) 0.36055(9) 0.0262(3) Uani d . . . 1 . .
H H7 1.081986 0.500595 0.344099 0.031 Uiso calc U . R 1 . .
C C8 1.1610(3) 0.38954(14) 0.42902(9) 0.0315(3) Uani d . . . 1 . .
H H8 1.32114 0.434015 0.45945 0.038 Uiso calc U . R 1 . .
C C10 0.8358(3) 0.22004(13) 0.40867(9) 0.0283(3) Uani d . . . 1 . .
H H10 0.774383 0.148096 0.424853 0.034 Uiso calc U . R 1 . .
C C11 0.6928(3) 0.26000(12) 0.34116(9) 0.0263(3) Uani d . . . 1 . .
H H11 0.531436 0.215968 0.311538 0.032 Uiso calc U . R 1 . .
C C12 1.2197(3) 0.24097(16) 0.52669(10) 0.0356(3) Uani d . . . 1 . .
C C13 0.3872(3) 0.83342(12) 0.26346(9) 0.0267(3) Uani d . . . 1 . .
H H13A 0.545913 0.852523 0.308871 0.032 Uiso calc U . R 1 . .
H H13B 0.236848 0.81296 0.292656 0.032 Uiso calc U . R 1 . .
C C14 0.3293(3) 0.94812(13) 0.22978(12) 0.0381(4) Uani d . . . 1 . .
H H14A 0.311999 1.02176 0.281035 0.046 Uiso calc U . R 1 . .
H H14B 0.159819 0.932743 0.189497 0.046 Uiso calc U . R 1 . .
C C15 0.5504(3) 0.97685(13) 0.17930(11) 0.0309(3) Uani d . . . 1 . .
H H15A 0.505473 1.049155 0.154526 0.037 Uiso calc U . R 1 . .
H H15B 0.716751 1.000083 0.220876 0.037 Uiso calc U . R 1 . .
C C16 0.5873(3) 0.86173(15) 0.10388(9) 0.0364(3) Uani d . . . 1 . .
H H16A 0.426897 0.844407 0.059214 0.044 Uiso calc U . R 1 . .
H H16B 0.737865 0.879158 0.07365 0.044 Uiso calc U . R 1 . .
C C17 0.6388(3) 0.74647(13) 0.13824(10) 0.0343(3) Uani d . . . 1 . .
H H17A 0.645111 0.671452 0.086952 0.041 Uiso calc U . R 1 . .
H H17B 0.812308 0.758836 0.176136 0.041 Uiso calc U . R 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.2268(14) ?
F1 C12 . 1.3357(17) ?
N1 C3 . 1.3769(15) ?
N1 N2 . 1.3771(13) ?
N1 C2 . 1.4523(14) ?
C1 N3 . 1.3472(15) ?
C1 C2 . 1.5320(16) ?
O2 C3 . 1.2222(15) ?
F2 C12 . 1.3368(19) ?
N2 C5 . 1.2830(16) ?
C2 H2A . 0.99 ?
C2 H2AB . 0.99 ?
C9 C8 . 1.381(2) ?
C9 C10 . 1.3914(19) ?
C9 C12 . 1.4991(18) ?
F3 C12 . 1.3392(18) ?
N3 C13 . 1.4587(16) ?
N3 C17 . 1.4679(15) ?
C3 C4 . 1.5068(17) ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 C6 . 1.4696(16) ?
C5 H5 . 0.95 ?
C6 C7 . 1.3915(17) ?
C6 C11 . 1.3986(17) ?
C7 C8 . 1.3896(19) ?
C7 H7 . 0.95 ?
C8 H8 . 0.95 ?
C10 C11 . 1.3807(18) ?
C10 H10 . 0.95 ?
C11 H11 . 0.95 ?
C13 C14 . 1.5089(19) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.5261(19) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.516(2) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 C17 . 1.515(2) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C17 H17A . 0.99 ?
C17 H17B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 N1 N2 . . 116.97(9) ?
C3 N1 C2 . . 120.59(10) ?
N2 N1 C2 . . 122.19(9) ?
O1 C1 N3 . . 123.01(11) ?
O1 C1 C2 . . 119.18(10) ?
N3 C1 C2 . . 117.81(10) ?
C5 N2 N1 . . 118.95(10) ?
N1 C2 C1 . . 110.44(9) ?
N1 C2 H2A . . 109.6 ?
C1 C2 H2A . . 109.6 ?
N1 C2 H2AB . . 109.6 ?
C1 C2 H2AB . . 109.6 ?
H2A C2 H2AB . . 108.1 ?
C8 C9 C10 . . 120.24(12) ?
C8 C9 C12 . . 121.18(13) ?
C10 C9 C12 . . 118.58(13) ?
C1 N3 C13 . . 119.98(10) ?
C1 N3 C17 . . 125.47(10) ?
C13 N3 C17 . . 114.34(10) ?
O2 C3 N1 . . 120.51(11) ?
O2 C3 C4 . . 122.23(11) ?
N1 C3 C4 . . 117.23(10) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
N2 C5 C6 . . 119.16(11) ?
N2 C5 H5 . . 120.4 ?
C6 C5 H5 . . 120.4 ?
C7 C6 C11 . . 119.17(11) ?
C7 C6 C5 . . 119.28(11) ?
C11 C6 C5 . . 121.56(11) ?
C8 C7 C6 . . 120.18(12) ?
C8 C7 H7 . . 119.9 ?
C6 C7 H7 . . 119.9 ?
C9 C8 C7 . . 120.11(12) ?
C9 C8 H8 . . 119.9 ?
C7 C8 H8 . . 119.9 ?
C11 C10 C9 . . 119.74(12) ?
C11 C10 H10 . . 120.1 ?
C9 C10 H10 . . 120.1 ?
C10 C11 C6 . . 120.55(12) ?
C10 C11 H11 . . 119.7 ?
C6 C11 H11 . . 119.7 ?
F1 C12 F2 . . 106.85(12) ?
F1 C12 F3 . . 106.20(13) ?
F2 C12 F3 . . 106.04(12) ?
F1 C12 C9 . . 112.05(11) ?
F2 C12 C9 . . 113.17(13) ?
F3 C12 C9 . . 112.06(12) ?
N3 C13 C14 . . 111.43(11) ?
N3 C13 H13A . . 109.3 ?
C14 C13 H13A . . 109.3 ?
N3 C13 H13B . . 109.3 ?
C14 C13 H13B . . 109.3 ?
H13A C13 H13B . . 108.0 ?
C13 C14 C15 . . 110.42(11) ?
C13 C14 H14A . . 109.6 ?
C15 C14 H14A . . 109.6 ?
C13 C14 H14B . . 109.6 ?
C15 C14 H14B . . 109.6 ?
H14A C14 H14B . . 108.1 ?
C16 C15 C14 . . 109.69(11) ?
C16 C15 H15A . . 109.7 ?
C14 C15 H15A . . 109.7 ?
C16 C15 H15B . . 109.7 ?
C14 C15 H15B . . 109.7 ?
H15A C15 H15B . . 108.2 ?
C17 C16 C15 . . 111.47(11) ?
C17 C16 H16A . . 109.3 ?
C15 C16 H16A . . 109.3 ?
C17 C16 H16B . . 109.3 ?
C15 C16 H16B . . 109.3 ?
H16A C16 H16B . . 108.0 ?
N3 C17 C16 . . 110.93(12) ?
N3 C17 H17A . . 109.5 ?
C16 C17 H17A . . 109.5 ?
N3 C17 H17B . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 108.0 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 N2 C5 . . . . -173.50(10) ?
C2 N1 N2 C5 . . . . 0.71(16) ?
C3 N1 C2 C1 . . . . 100.21(12) ?
N2 N1 C2 C1 . . . . -73.79(13) ?
O1 C1 C2 N1 . . . . -22.74(15) ?
N3 C1 C2 N1 . . . . 157.97(10) ?
O1 C1 N3 C13 . . . . 6.22(18) ?
C2 C1 N3 C13 . . . . -174.53(10) ?
O1 C1 N3 C17 . . . . -179.41(13) ?
C2 C1 N3 C17 . . . . -0.15(18) ?
N2 N1 C3 O2 . . . . 174.77(10) ?
C2 N1 C3 O2 . . . . 0.46(17) ?
N2 N1 C3 C4 . . . . -6.81(15) ?
C2 N1 C3 C4 . . . . 178.88(10) ?
N1 N2 C5 C6 . . . . 179.67(9) ?
N2 C5 C6 C7 . . . . 172.15(11) ?
N2 C5 C6 C11 . . . . -7.68(17) ?
C11 C6 C7 C8 . . . . 0.07(19) ?
C5 C6 C7 C8 . . . . -179.76(12) ?
C10 C9 C8 C7 . . . . -0.1(2) ?
C12 C9 C8 C7 . . . . -179.83(12) ?
C6 C7 C8 C9 . . . . 0.3(2) ?
C8 C9 C10 C11 . . . . -0.5(2) ?
C12 C9 C10 C11 . . . . 179.26(12) ?
C9 C10 C11 C6 . . . . 0.9(2) ?
C7 C6 C11 C10 . . . . -0.65(19) ?
C5 C6 C11 C10 . . . . 179.18(12) ?
C8 C9 C12 F1 . . . . 126.70(15) ?
C10 C9 C12 F1 . . . . -53.09(19) ?
C8 C9 C12 F2 . . . . 5.80(19) ?
C10 C9 C12 F2 . . . . -173.98(12) ?
C8 C9 C12 F3 . . . . -114.04(15) ?
C10 C9 C12 F3 . . . . 66.18(16) ?
C1 N3 C13 C14 . . . . -129.99(12) ?
C17 N3 C13 C14 . . . . 55.04(15) ?
N3 C13 C14 C15 . . . . -55.48(16) ?
C13 C14 C15 C16 . . . . 56.14(17) ?
C14 C15 C16 C17 . . . . -55.67(16) ?
C1 N3 C17 C16 . . . . 131.63(13) ?
C13 N3 C17 C16 . . . . -53.71(16) ?
C15 C16 C17 N3 . . . . 53.79(16) ?



