# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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 
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data_ia1017e
_database_code_depnum_ccdc_archive 'CCDC 1851243'
loop_
_audit_author_name
_audit_author_address
'Richard Staples'
;Department of Chemistry, Michigan State University
United States of America
;
_audit_update_record             
;
2018-06-23 deposited with the CCDC.	2019-07-19 downloaded from the CCDC.
;
_audit_creation_date             2017-10-16
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H23 N3 O2'
_chemical_formula_sum            'C22 H23 N3 O2'
_chemical_formula_weight         361.43
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8408(14)
_cell_length_b                   7.6010(11)
_cell_length_c                   25.340(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.827(2)
_cell_angle_gamma                90
_cell_volume                     1893.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9800
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.28
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0686 before and 0.0635 after correction. The Ratio of minimum to maximum transmission is 0.9202. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       chunk
_exptl_crystal_F_000             768
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.207
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega scans of 0.5° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structures are solved 
by the direct method using the SHELXS-97 program and refined by least squares 
method on F2, SHELXL-97, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            28100
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.400
_diffrn_reflns_theta_min         1.609
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2719
_reflns_number_total             3462
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0654P)²+0.3101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1246
_refine_special_details          
'The structure was refined by Least Squares using version 2014/6 of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C11-N2A \\sim C11B-N2
 with sigma of 0.02
 N1-N2 \\sim N1-N2A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C13B) = Uanis(C14)
Uanis(N2A) = Uanis(N2)
Uanis(C21) = Uanis(C22B)
4. Others
 Sof(N2)=Sof(H2)=Sof(N3B)=Sof(C11B)=Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(C14B)=
 Sof(H14B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(C17B)=Sof(H17B)=Sof(C18B)=
 Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(H20B)=Sof(C21B)=Sof(H21D)=Sof(H21E)=
 Sof(H21F)=Sof(C22B)=Sof(H22D)=Sof(H22E)=Sof(H22F)=1-FVAR(1)
 Sof(N2A)=Sof(H2A)=Sof(N3)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=
 Sof(C14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=
 Sof(C19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22)=
 Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N2A(H2A), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12),
 C12B(H12B), C13(H13), C14B(H14B), C15(H15), C15B(H15B), C17(H17), C17B(H17B),
 C18(H18), C19B(H19B), C20(H20), C20B(H20B)
5.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C21(H21A,H21B,H21C), C21B(H21D,H21E,H21F), C22(H22A,H22B,
 H22C), C22B(H22D,H22E,H22F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.24377(9) 0.59534(13) 0.58766(4) 0.0428(3) Uani 1 1 d . . . . .
O2 O 0.28534(11) 0.72140(15) 0.51027(4) 0.0526(3) Uani 1 1 d . . . . .
N1 N 0.56949(12) 0.69714(16) 0.53888(5) 0.0428(3) Uani 1 1 d D . . . .
N2 N 0.5637(11) 0.761(2) 0.4912(5) 0.0411(8) Uani 0.318(3) 1 d D . P A 2
H2 H 0.4838 0.7752 0.4745 0.049 Uiso 0.318(3) 1 calc R . P A 2
N2A N 0.5302(4) 0.7764(10) 0.4930(2) 0.0411(8) Uani 0.682(3) 1 d D . P A 1
H2A H 0.4432 0.7944 0.4852 0.049 Uiso 0.682(3) 1 calc R . P A 1
N3 N 1.1340(7) 1.0390(7) 0.3155(3) 0.0500(10) Uani 0.682(3) 1 d . . P A 1
N3B N 1.1138(14) 1.0948(16) 0.3061(5) 0.054(2) Uani 0.318(3) 1 d . . P A 2
C1 C 0.47318(14) 0.64224(18) 0.56875(5) 0.0381(3) Uani 1 1 d . . . . .
C2 C 0.32708(15) 0.65864(18) 0.55242(6) 0.0398(3) Uani 1 1 d . . . . .
C3 C 0.09922(14) 0.6087(2) 0.57391(6) 0.0477(4) Uani 1 1 d . . . . .
H3A H 0.0752 0.5362 0.5424 0.057 Uiso 1 1 calc R . . . .
H3B H 0.0741 0.7324 0.5660 0.057 Uiso 1 1 calc R . . . .
C4 C 0.02557(17) 0.5436(2) 0.62055(7) 0.0556(4) Uani 1 1 d . . . . .
H4A H -0.0728 0.5481 0.6124 0.083 Uiso 1 1 calc GR . . . .
H4B H 0.0486 0.6180 0.6513 0.083 Uiso 1 1 calc GR . . . .
H4C H 0.0528 0.4220 0.6284 0.083 Uiso 1 1 calc GR . . . .
C5 C 0.52149(14) 0.55348(18) 0.61850(6) 0.0387(3) Uani 1 1 d . . . . .
C6 C 0.45647(15) 0.5701(2) 0.66596(6) 0.0465(4) Uani 1 1 d . . . . .
H6 H 0.3758 0.6383 0.6671 0.056 Uiso 1 1 calc R . . . .
C7 C 0.50850(17) 0.4878(2) 0.71145(6) 0.0553(4) Uani 1 1 d . . . . .
H7 H 0.4631 0.4998 0.7435 0.066 Uiso 1 1 calc R . . . .
C8 C 0.62625(17) 0.3882(2) 0.71051(7) 0.0576(4) Uani 1 1 d . . . . .
H8 H 0.6611 0.3311 0.7416 0.069 Uiso 1 1 calc R . . . .
C9 C 0.69242(16) 0.3727(2) 0.66415(7) 0.0511(4) Uani 1 1 d . . . . .
H9 H 0.7741 0.3063 0.6635 0.061 Uiso 1 1 calc R . . . .
C10 C 0.64072(15) 0.45336(19) 0.61854(6) 0.0436(4) Uani 1 1 d . . . . .
H10 H 0.6869 0.4405 0.5867 0.052 Uiso 1 1 calc R . . . .
C11 C 0.6283(4) 0.8305(5) 0.45743(17) 0.0348(9) Uani 0.682(3) 1 d D . P A 1
C11B C 0.6816(9) 0.8086(11) 0.4658(3) 0.0331(19) Uani 0.318(3) 1 d D . P A 2
C12 C 0.5795(3) 0.8911(3) 0.40681(9) 0.0419(6) Uani 0.682(3) 1 d . . P A 1
H12 H 0.4842 0.8971 0.3989 0.050 Uiso 0.682(3) 1 calc R . P A 1
C12B C 0.6615(6) 0.8659(6) 0.4164(2) 0.0412(13) Uani 0.318(3) 1 d . . P A 2
H12B H 0.5716 0.8729 0.4011 0.049 Uiso 0.318(3) 1 calc R . P A 2
C13 C 0.6664(2) 0.9406(3) 0.36960(8) 0.0421(6) Uani 0.682(3) 1 d . . P A 1
H13 H 0.6310 0.9780 0.3359 0.050 Uiso 0.682(3) 1 calc R . P A 1
C13B C 0.7733(13) 0.9167(19) 0.3864(6) 0.0373(9) Uani 0.318(3) 1 d . . P A 2
C14 C 0.8096(5) 0.9374(7) 0.3802(3) 0.0373(9) Uani 0.682(3) 1 d . . P A 1
C14B C 0.7631(5) 0.9743(7) 0.33443(18) 0.0447(13) Uani 0.318(3) 1 d . . P A 2
H14B H 0.6761 0.9770 0.3164 0.054 Uiso 0.318(3) 1 calc R . P A 2
C15 C 0.9011(3) 0.9893(3) 0.34168(11) 0.0402(6) Uani 0.682(3) 1 d . . P A 1
H15 H 0.8660 1.0240 0.3077 0.048 Uiso 0.682(3) 1 calc R . P A 1
C15B C 0.8741(5) 1.0275(8) 0.3083(3) 0.0527(14) Uani 0.318(3) 1 d . . P A 2
H15B H 0.8626 1.0648 0.2726 0.063 Uiso 0.318(3) 1 calc R . P A 2
C16 C 1.0402(5) 0.9908(5) 0.35225(19) 0.0401(9) Uani 0.682(3) 1 d . . P A 1
C16B C 1.0077(10) 1.0280(12) 0.3337(4) 0.045(2) Uani 0.318(3) 1 d . . P A 2
C17 C 1.0883(3) 0.9362(3) 0.40371(11) 0.0416(6) Uani 0.682(3) 1 d . . P A 1
H17 H 1.1833 0.9379 0.4124 0.050 Uiso 0.682(3) 1 calc R . P A 1
C17B C 1.0213(7) 0.9639(8) 0.3835(3) 0.0419(14) Uani 0.318(3) 1 d . . P A 2
H17B H 1.1101 0.9558 0.3998 0.050 Uiso 0.318(3) 1 calc R . P A 2
C18 C 1.0017(2) 0.8818(3) 0.44078(9) 0.0403(6) Uani 0.682(3) 1 d . . P A 1
H18 H 1.0382 0.8439 0.4743 0.048 Uiso 0.682(3) 1 calc R . P A 1
C18B C 0.9077(7) 0.9073(8) 0.4131(3) 0.0384(14) Uani 0.318(3) 1 d . . P A 2
C19 C 0.8581(3) 0.8801(3) 0.43079(13) 0.0363(7) Uani 0.682(3) 1 d . . P A 1
C19B C 0.9201(5) 0.8428(6) 0.4644(2) 0.0410(13) Uani 0.318(3) 1 d . . P A 2
H19B H 1.0083 0.8322 0.4811 0.049 Uiso 0.318(3) 1 calc R . P A 2
C20 C 0.7659(4) 0.8259(4) 0.46883(13) 0.0374(7) Uani 0.682(3) 1 d . . P A 1
H20 H 0.7998 0.7861 0.5025 0.045 Uiso 0.682(3) 1 calc R . P A 1
C20B C 0.8113(7) 0.7949(8) 0.4911(3) 0.0416(14) Uani 0.318(3) 1 d . . P A 2
H20B H 0.8220 0.7527 0.5263 0.050 Uiso 0.318(3) 1 calc R . P A 2
C21 C 1.256(2) 1.113(2) 0.3337(8) 0.0603(9) Uani 0.682(3) 1 d . . P A 1
H21A H 1.2453 1.1641 0.3687 0.090 Uiso 0.682(3) 1 calc GR . P A 1
H21B H 1.2827 1.2045 0.3091 0.090 Uiso 0.682(3) 1 calc GR . P A 1
H21C H 1.3263 1.0213 0.3360 0.090 Uiso 0.682(3) 1 calc GR . P A 1
C21B C 1.1187(16) 1.085(3) 0.2505(6) 0.081(4) Uani 0.318(3) 1 d . . P A 2
H21D H 1.1521 0.9687 0.2405 0.122 Uiso 0.318(3) 1 calc GR . P A 2
H21E H 1.1802 1.1759 0.2382 0.122 Uiso 0.318(3) 1 calc GR . P A 2
H21F H 1.0273 1.1034 0.2343 0.122 Uiso 0.318(3) 1 calc GR . P A 2
C22 C 1.0819(7) 1.0974(10) 0.2631(3) 0.0700(15) Uani 0.682(3) 1 d . . P A 1
H22A H 1.0203 1.0080 0.2476 0.105 Uiso 0.682(3) 1 calc GR . P A 1
H22B H 1.1581 1.1149 0.2402 0.105 Uiso 0.682(3) 1 calc GR . P A 1
H22C H 1.0325 1.2085 0.2666 0.105 Uiso 0.682(3) 1 calc GR . P A 1
C22B C 1.259(4) 1.123(5) 0.3328(16) 0.0603(9) Uani 0.318(3) 1 d . . P A 2
H22D H 1.2558 1.2199 0.3583 0.090 Uiso 0.318(3) 1 calc GR . P A 2
H22E H 1.3228 1.1527 0.3057 0.090 Uiso 0.318(3) 1 calc GR . P A 2
H22F H 1.2886 1.0153 0.3510 0.090 Uiso 0.318(3) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3317(17) . ?
O1 C3 1.4513(17) . ?
O2 C2 1.2222(17) . ?
N1 N2 1.301(12) . ?
N1 N2A 1.349(5) . ?
N1 C1 1.3099(18) . ?
N2 H2 0.8800 . ?
N2 C11B 1.402(12) . ?
N2A H2A 0.8800 . ?
N2A C11 1.414(6) . ?
N3 C16 1.392(9) . ?
N3 C21 1.38(2) . ?
N3 C22 1.468(10) . ?
N3B C16B 1.381(18) . ?
N3B C21B 1.41(2) . ?
N3B C22B 1.56(5) . ?
C1 C2 1.482(2) . ?
C1 C5 1.487(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.501(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.396(2) . ?
C5 C10 1.398(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.387(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.376(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.424(5) . ?
C11 C20 1.372(4) . ?
C11B C12B 1.330(10) . ?
C11B C20B 1.404(8) . ?
C12 H12 0.9500 . ?
C12 C13 1.357(3) . ?
C12B H12B 0.9500 . ?
C12B C13B 1.422(12) . ?
C13 H13 0.9500 . ?
C13 C14 1.421(6) . ?
C13B C14B 1.387(17) . ?
C13B C18B 1.457(17) . ?
C14 C15 1.417(5) . ?
C14 C19 1.414(8) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.366(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(5) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.436(10) . ?
C16 C17 1.427(4) . ?
C16B C17B 1.353(10) . ?
C17 H17 0.9500 . ?
C17 C18 1.364(3) . ?
C17B H17B 0.9500 . ?
C17B C18B 1.442(10) . ?
C18 H18 0.9500 . ?
C18 C19 1.423(4) . ?
C18B C19B 1.390(9) . ?
C19 C20 1.417(5) . ?
C19B H19B 0.9500 . ?
C19B C20B 1.345(8) . ?
C20 H20 0.9500 . ?
C20B H20B 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C3 116.24(11) . . ?
N2 N1 C1 131.0(5) . . ?
C1 N1 N2A 117.1(2) . . ?
N1 N2 H2 119.2 . . ?
N1 N2 C11B 121.5(9) . . ?
C11B N2 H2 119.2 . . ?
N1 N2A H2A 119.9 . . ?
N1 N2A C11 120.2(3) . . ?
C11 N2A H2A 119.9 . . ?
C16 N3 C22 118.1(6) . . ?
C21 N3 C16 118.5(9) . . ?
C21 N3 C22 115.9(9) . . ?
C16B N3B C21B 123.3(13) . . ?
C16B N3B C22B 121.9(16) . . ?
C21B N3B C22B 111.2(17) . . ?
N1 C1 C2 122.12(13) . . ?
N1 C1 C5 115.10(12) . . ?
C2 C1 C5 122.69(12) . . ?
O1 C2 C1 113.79(12) . . ?
O2 C2 O1 122.39(13) . . ?
O2 C2 C1 123.81(13) . . ?
O1 C3 H3A 110.3 . . ?
O1 C3 H3B 110.3 . . ?
O1 C3 C4 107.07(13) . . ?
H3A C3 H3B 108.6 . . ?
C4 C3 H3A 110.3 . . ?
C4 C3 H3B 110.3 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C1 123.28(13) . . ?
C6 C5 C10 117.96(14) . . ?
C10 C5 C1 118.72(12) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.63(14) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.44(15) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.55(15) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.36(15) . . ?
C10 C9 H9 119.8 . . ?
C5 C10 H10 119.5 . . ?
C9 C10 C5 121.06(14) . . ?
C9 C10 H10 119.5 . . ?
N2A C11 C12 117.2(3) . . ?
C20 C11 N2A 123.8(4) . . ?
C20 C11 C12 118.9(4) . . ?
N2 C11B C20B 121.7(8) . . ?
C12B C11B N2 115.3(9) . . ?
C12B C11B C20B 122.9(7) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 H12 119.4 . . ?
C11B C12B H12B 119.7 . . ?
C11B C12B C13B 120.6(9) . . ?
C13B C12B H12B 119.7 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.1(3) . . ?
C14 C13 H13 119.4 . . ?
C12B C13B C18B 116.6(11) . . ?
C14B C13B C12B 124.9(11) . . ?
C14B C13B C18B 118.5(8) . . ?
C15 C14 C13 121.5(5) . . ?
C19 C14 C13 117.7(3) . . ?
C19 C14 C15 120.8(4) . . ?
C13B C14B H14B 118.9 . . ?
C15B C14B C13B 122.1(7) . . ?
C15B C14B H14B 118.9 . . ?
C14 C15 H15 119.1 . . ?
C16 C15 C14 121.7(4) . . ?
C16 C15 H15 119.1 . . ?
C14B C15B H15B 119.3 . . ?
C14B C15B C16B 121.3(7) . . ?
C16B C15B H15B 119.3 . . ?
N3 C16 C17 119.1(4) . . ?
C15 C16 N3 123.7(4) . . ?
C15 C16 C17 117.1(4) . . ?
N3B C16B C15B 118.2(8) . . ?
C17B C16B N3B 124.2(8) . . ?
C17B C16B C15B 117.6(8) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.8(3) . . ?
C18 C17 H17 119.1 . . ?
C16B C17B H17B 118.3 . . ?
C16B C17B C18B 123.3(7) . . ?
C18B C17B H17B 118.3 . . ?
C17 C18 H18 119.0 . . ?
C17 C18 C19 121.9(3) . . ?
C19 C18 H18 119.0 . . ?
C17B C18B C13B 117.0(7) . . ?
C19B C18B C13B 119.2(8) . . ?
C19B C18B C17B 123.9(7) . . ?
C14 C19 C18 116.5(3) . . ?
C14 C19 C20 120.4(3) . . ?
C20 C19 C18 123.0(3) . . ?
C18B C19B H19B 119.0 . . ?
C20B C19B C18B 122.0(6) . . ?
C20B C19B H19B 119.0 . . ?
C11 C20 C19 120.5(4) . . ?
C11 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C11B C20B H20B 120.7 . . ?
C19B C20B C11B 118.6(6) . . ?
C19B C20B H20B 120.7 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3B C21B H21D 109.5 . . ?
N3B C21B H21E 109.5 . . ?
N3B C21B H21F 109.5 . . ?
H21D C21B H21E 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3B C22B H22D 109.5 . . ?
N3B C22B H22E 109.5 . . ?
N3B C22B H22F 109.5 . . ?
H22D C22B H22E 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?

_contact_Crystallographer_email  staples@chemistry.msu.com
_contact_Crystallographer_name   'Richard Staples'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id BHS-NapNCH3
_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_ia718a
_database_code_depnum_ccdc_archive 'CCDC 1860816'
loop_
_audit_author_name
_audit_author_address
'Richard Staples'
;Department of Chemistry, Michigan State University
United States of America
;
_audit_update_record             
;
2018-08-07 deposited with the CCDC.	2019-07-19 downloaded from the CCDC.
;
_audit_creation_method           Olex2


_audit_creation_date             2018-08-07
_chemical_formula_sum            'C22 H22 N4 O4'
_chemical_formula_weight         406.430
_refine_ls_R_factor_all          0.070
_cell_length_a                   8.1890(1)
_cell_length_b                   10.2031(2)
_cell_length_c                   12.0424(2)
_cell_angle_alpha                81.626(1)
_cell_angle_beta                 83.017(1)
_cell_angle_gamma                89.043(1)
_cell_volume                     988.1(0)
_cell_formula_units_Z            2
_symmetry_int_tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  -P_1

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
O ? 1.200
N ? 1.200
H ? 1.200
C ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
O1 O 0.2943(2) 0.4316(1) 0.8098(1) 1.000 2 i ? d Uani 0.0359(3)
O2 O 0.5312(2) 0.4692(1) 0.6972(1) 1.000 2 i ? d Uani 0.0391(3)
O3 O -0.3395(2) 0.0159(1) 0.6554(1) 1.000 2 i ? d Uani 0.0545(4)
O4 O -0.4200(2) 0.1454(2) 0.7787(1) 1.000 2 i ? d Uani 0.0503(4)
N1 N 0.4245(2) 0.2968(1) 0.5552(1) 1.000 2 i ? d Uani 0.0323(4)
N2 N 0.5788(2) 0.3353(2) 0.5304(1) 1.000 2 i ? d Uani 0.0339(4)
H2 H 0.617(3) 0.390(2) 0.5715(18) 1.000 2 i ? d Uiso 0.042(6)
N3 N -0.3149(2) 0.1041(2) 0.7100(1) 1.000 2 i ? d Uani 0.0396(4)
N4 N 1.2648(2) 0.1723(2) 0.0606(2) 1.000 2 i ? d Uani 0.0502(5)
C1 C 0.3308(2) 0.3335(2) 0.6418(2) 1.000 2 i ? d Uani 0.0312(4)
C2 C 0.3950(2) 0.4180(2) 0.7167(2) 1.000 2 i ? d Uani 0.0316(4)
C3 C 0.3533(2) 0.5193(2) 0.8810(2) 1.000 2 i ? d Uani 0.0422(5)
H3A H 0.3869 0.6055 0.8354 1.000 2 i ? calc Uiso 0.05100
H3B H 0.4498 0.4797 0.9155 1.000 2 i ? calc Uiso 0.05100
C4 C 0.2164(3) 0.5390(2) 0.9711(2) 1.000 2 i ? d Uani 0.0458(5)
H4A H 0.1218 0.5786 0.9360 1.000 2 i ? calc Uiso 0.06900
H4B H 0.2532 0.5980 1.0204 1.000 2 i ? calc Uiso 0.06900
H4C H 0.1843 0.4532 1.0158 1.000 2 i ? calc Uiso 0.06900
C5 C 0.1615(2) 0.2775(2) 0.6610(2) 1.000 2 i ? d Uani 0.0304(4)
C6 C 0.0277(2) 0.3360(2) 0.7196(2) 1.000 2 i ? d Uani 0.0341(4)
H6 H 0.0439 0.4160 0.7486 1.000 2 i ? calc Uiso 0.04100
C7 C -0.1270(2) 0.2795(2) 0.7361(2) 1.000 2 i ? d Uani 0.0345(4)
H7 H -0.2162 0.3194 0.7771 1.000 2 i ? calc Uiso 0.04100
C8 C -0.1504(2) 0.1645(2) 0.6924(2) 1.000 2 i ? d Uani 0.0319(4)
C9 C -0.0231(2) 0.1055(2) 0.6318(2) 1.000 2 i ? d Uani 0.0356(4)
H9 H -0.0420 0.0276 0.6006 1.000 2 i ? calc Uiso 0.04300
C10 C 0.1322(2) 0.1611(2) 0.6170(2) 1.000 2 i ? d Uani 0.0337(4)
H10 H 0.2205 0.1198 0.5765 1.000 2 i ? calc Uiso 0.04000
C11 C 0.6810(2) 0.2892(2) 0.4421(2) 1.000 2 i ? d Uani 0.0320(4)
C12 C 0.6226(2) 0.2000(2) 0.3767(2) 1.000 2 i ? d Uani 0.0368(4)
H12 H 0.5123 0.1690 0.3921 1.000 2 i ? calc Uiso 0.04400
C13 C 0.7262(2) 0.1588(2) 0.2911(2) 1.000 2 i ? d Uani 0.0369(4)
H13 H 0.6860 0.0989 0.2474 1.000 2 i ? calc Uiso 0.04400
C14 C 0.8916(2) 0.2022(2) 0.2653(2) 1.000 2 i ? d Uani 0.0319(4)
C15 C 0.9992(2) 0.1622(2) 0.1751(2) 1.000 2 i ? d Uani 0.0362(4)
H15 H 0.9588 0.1058 0.1285 1.000 2 i ? calc Uiso 0.04300
C16 C 1.1611(2) 0.2030(2) 0.1531(2) 1.000 2 i ? d Uani 0.0368(4)
C17 C 1.2204(2) 0.2835(2) 0.2272(2) 1.000 2 i ? d Uani 0.0384(4)
H17 H 1.3328 0.3094 0.2158 1.000 2 i ? calc Uiso 0.04600
C18 C 1.1187(2) 0.3240(2) 0.3140(2) 1.000 2 i ? d Uani 0.0365(4)
H18 H 1.1617 0.3782 0.3615 1.000 2 i ? calc Uiso 0.04400
C19 C 0.9511(2) 0.2874(2) 0.3351(2) 1.000 2 i ? d Uani 0.0310(4)
C20 C 0.8414(2) 0.3304(2) 0.4227(2) 1.000 2 i ? d Uani 0.0325(4)
H20 H 0.8797 0.3888 0.4686 1.000 2 i ? calc Uiso 0.03900
C21 C 1.2019(3) 0.0955(3) -0.0171(2) 1.000 2 i ? d Uani 0.0562(6)
H21A H 1.1794 0.0048 0.0205 1.000 2 i ? calc Uiso 0.08400
H21B H 1.2837 0.0940 -0.0835 1.000 2 i ? calc Uiso 0.08400
H21C H 1.1001 0.1359 -0.0410 1.000 2 i ? calc Uiso 0.08400
C22 C 1.4397(2) 0.1767(2) 0.0571(2) 1.000 2 i ? d Uani 0.0477(5)
H22A H 1.4732 0.2654 0.0675 1.000 2 i ? calc Uiso 0.07200
H22B H 1.4912 0.1563 -0.0162 1.000 2 i ? calc Uiso 0.07200
H22C H 1.4745 0.1113 0.1177 1.000 2 i ? calc Uiso 0.07200



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . . 1.332(2) no
O1 C3 . . 1.452(2) no
O2 C2 . . 1.222(2) no
O3 N3 . . 1.223(2) no
O4 N3 . . 1.233(2) no
N1 N2 . . 1.316(2) no
N1 C1 . . 1.314(2) no
N2 H2 . . 0.88(2) no
N2 C11 . . 1.403(2) no
N3 C8 . . 1.469(2) no
N4 C16 . . 1.387(2) no
N4 C21 . . 1.448(3) no
N4 C22 . . 1.429(2) no
C1 C2 . . 1.479(2) no
C1 C5 . . 1.487(2) no
C3 H3A . . 0.9900 no
C3 H3B . . 0.9900 no
C3 C4 . . 1.495(3) no
C4 H4A . . 0.9800 no
C4 H4B . . 0.9800 no
C4 H4C . . 0.9800 no
C5 C6 . . 1.403(2) no
C5 C10 . . 1.404(2) no
C6 H6 . . 0.9500 no
C6 C7 . . 1.381(2) no
C7 H7 . . 0.9500 no
C7 C8 . . 1.379(3) no
C8 C9 . . 1.380(3) no
C9 H9 . . 0.9500 no
C9 C10 . . 1.382(2) no
C10 H10 . . 0.9500 no
C11 C12 . . 1.411(3) no
C11 C20 . . 1.369(2) no
C12 H12 . . 0.9500 no
C12 C13 . . 1.364(3) no
C13 H13 . . 0.9500 no
C13 C14 . . 1.416(3) no
C14 C15 . . 1.417(3) no
C14 C19 . . 1.424(2) no
C15 H15 . . 0.9500 no
C15 C16 . . 1.379(3) no
C16 C17 . . 1.428(3) no
C17 H17 . . 0.9500 no
C17 C18 . . 1.364(3) no
C18 H18 . . 0.9500 no
C18 C19 . . 1.412(2) no
C19 C20 . . 1.415(3) no
C20 H20 . . 0.9500 no
C21 H21A . . 0.9800 no
C21 H21B . . 0.9800 no
C21 H21C . . 0.9800 no
C22 H22A . . 0.9800 no
C22 H22B . . 0.9800 no
C22 H22C . . 0.9800 no

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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C3 . . . 115.06(14) no
C1 N1 N2 . . . 121.38(16) no
N1 N2 H2 . . . 118.2(14) no
N1 N2 C11 . . . 121.05(16) no
C11 N2 H2 . . . 120.7(14) no
O3 N3 O4 . . . 123.81(17) no
O3 N3 C8 . . . 117.97(17) no
O4 N3 C8 . . . 118.22(16) no
C16 N4 C21 . . . 119.39(17) no
C16 N4 C22 . . . 121.56(17) no
C22 N4 C21 . . . 116.23(16) no
N1 C1 C2 . . . 121.46(16) no
N1 C1 C5 . . . 114.71(16) no
C2 C1 C5 . . . 123.74(16) no
O1 C2 C1 . . . 114.81(15) no
O2 C2 O1 . . . 121.83(17) no
O2 C2 C1 . . . 123.33(17) no
O1 C3 H3A . . . 110.10 no
O1 C3 H3B . . . 110.10 no
O1 C3 C4 . . . 107.84(16) no
H3A C3 H3B . . . 108.50 no
C4 C3 H3A . . . 110.10 no
C4 C3 H3B . . . 110.10 no
C3 C4 H4A . . . 109.50 no
C3 C4 H4B . . . 109.50 no
C3 C4 H4C . . . 109.50 no
H4A C4 H4B . . . 109.50 no
H4A C4 H4C . . . 109.50 no
H4B C4 H4C . . . 109.50 no
C6 C5 C1 . . . 123.37(16) no
C6 C5 C10 . . . 117.82(17) no
C10 C5 C1 . . . 118.81(16) no
C5 C6 H6 . . . 119.40 no
C7 C6 C5 . . . 121.22(17) no
C7 C6 H6 . . . 119.40 no
C6 C7 H7 . . . 120.40 no
C8 C7 C6 . . . 119.16(17) no
C8 C7 H7 . . . 120.40 no
C7 C8 N3 . . . 119.24(17) no
C7 C8 C9 . . . 121.47(17) no
C9 C8 N3 . . . 119.29(16) no
C8 C9 H9 . . . 120.40 no
C8 C9 C10 . . . 119.25(17) no
C10 C9 H9 . . . 120.40 no
C5 C10 H10 . . . 119.50 no
C9 C10 C5 . . . 121.05(17) no
C9 C10 H10 . . . 119.50 no
N2 C11 C12 . . . 121.46(17) no
C20 C11 N2 . . . 118.04(16) no
C20 C11 C12 . . . 120.48(17) no
C11 C12 H12 . . . 120.30 no
C13 C12 C11 . . . 119.32(17) no
C13 C12 H12 . . . 120.30 no
C12 C13 H13 . . . 118.90 no
C12 C13 C14 . . . 122.27(18) no
C14 C13 H13 . . . 118.90 no
C13 C14 C15 . . . 122.75(17) no
C13 C14 C19 . . . 117.85(17) no
C15 C14 C19 . . . 119.39(17) no
C14 C15 H15 . . . 119.10 no
C16 C15 C14 . . . 121.84(17) no
C16 C15 H15 . . . 119.10 no
N4 C16 C17 . . . 119.62(17) no
C15 C16 N4 . . . 122.47(18) no
C15 C16 C17 . . . 117.87(18) no
C16 C17 H17 . . . 119.40 no
C18 C17 C16 . . . 121.28(18) no
C18 C17 H17 . . . 119.40 no
C17 C18 H18 . . . 119.20 no
C17 C18 C19 . . . 121.54(18) no
C19 C18 H18 . . . 119.20 no
C18 C19 C14 . . . 117.97(17) no
C18 C19 C20 . . . 122.95(17) no
C20 C19 C14 . . . 119.08(16) no
C11 C20 C19 . . . 120.89(17) no
C11 C20 H20 . . . 119.60 no
C19 C20 H20 . . . 119.60 no
N4 C21 H21A . . . 109.50 no
N4 C21 H21B . . . 109.50 no
N4 C21 H21C . . . 109.50 no
H21A C21 H21B . . . 109.50 no
H21A C21 H21C . . . 109.50 no
H21B C21 H21C . . . 109.50 no
N4 C22 H22A . . . 109.50 no
N4 C22 H22B . . . 109.50 no
N4 C22 H22C . . . 109.50 no
H22A C22 H22B . . . 109.50 no
H22A C22 H22C . . . 109.50 no
H22B C22 H22C . . . 109.50 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_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 O2 . . . 0.88(2) 1.87(2) 2.578(2) 135.2(19) yes

