# Electronic Supplementary Material (ESI) for RSC Advances.
# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_18005_a
_database_code_depnum_ccdc_archive 'CCDC 1867840'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2018-09-14 deposited with the CCDC.	2019-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 N4 O2'
_chemical_formula_sum            'C19 H20 N4 O2'
_chemical_formula_weight         336.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.2422(7)
_cell_length_b                   8.7080(5)
_cell_length_c                   29.4352(16)
_cell_angle_alpha                90
_cell_angle_beta                 96.420(3)
_cell_angle_gamma                90
_cell_volume                     3373.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      5.30
_cell_measurement_theta_max      68.19

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.101
_exptl_absorpt_coefficient_mu    0.717
_shelx_estimated_absorpt_T_min   0.850
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6401
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58291
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.021
_diffrn_reflns_theta_max         68.433
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6189
_reflns_number_gt                5301
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+0.7521P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00088(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6189
_refine_ls_number_parameters     458
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.73524(7) 0.08466(10) 0.28919(3) 0.0246(2) Uani 1 1 d . U . . .
N1 N 0.49617(8) 0.90488(13) 0.17029(4) 0.0222(2) Uani 1 1 d . . . . .
C1 C 0.42090(10) 0.88361(16) 0.13097(5) 0.0248(3) Uani 1 1 d . . . . .
H1A H 0.396243 0.981921 0.119921 0.037 Uiso 1 1 calc R U . . .
H1B H 0.365355 0.823757 0.139731 0.037 Uiso 1 1 calc R U . . .
H1C H 0.451355 0.831078 0.107265 0.037 Uiso 1 1 calc R U . . .
N2 N 0.83010(8) 0.46998(12) 0.30926(4) 0.0171(2) Uani 1 1 d . . . . .
O2 O 0.86836(7) 0.18407(10) 0.33377(3) 0.0216(2) Uani 1 1 d . . . . .
C2 C 0.53280(11) 1.05954(15) 0.18044(5) 0.0256(3) Uani 1 1 d . . . . .
H2A H 0.598041 1.072487 0.169639 0.038 Uiso 1 1 calc R U . . .
H2B H 0.538851 1.076143 0.212868 0.038 Uiso 1 1 calc R U . . .
H2C H 0.485728 1.132296 0.165514 0.038 Uiso 1 1 calc R U . . .
N3 N 0.80527(8) 0.56712(12) 0.34287(4) 0.0197(2) Uani 1 1 d . . . . .
C3 C 0.54186(9) 0.78129(15) 0.19245(4) 0.0188(3) Uani 1 1 d . . . . .
N4 N 0.88334(8) 0.65371(12) 0.35581(4) 0.0209(2) Uani 1 1 d . . . . .
C4 C 0.51026(10) 0.63008(15) 0.18137(4) 0.0203(3) Uani 1 1 d . . . . .
H4 H 0.457528 0.613507 0.158256 0.024 Uiso 1 1 calc R U . . .
C5 C 0.55624(10) 0.50703(15) 0.20423(4) 0.0203(3) Uani 1 1 d . . . . .
H5 H 0.532837 0.408771 0.196432 0.024 Uiso 1 1 calc R U . . .
C6 C 0.63721(9) 0.52355(15) 0.23890(4) 0.0184(3) Uani 1 1 d . . . . .
C7 C 0.66847(10) 0.67452(15) 0.24988(4) 0.0198(3) Uani 1 1 d . . . . .
H7 H 0.721860 0.690371 0.272728 0.024 Uiso 1 1 calc R U . . .
C8 C 0.62237(10) 0.79943(15) 0.22781(4) 0.0201(3) Uani 1 1 d . . . . .
H8 H 0.644569 0.897705 0.236312 0.024 Uiso 1 1 calc R U . . .
C9 C 0.67990(10) 0.38472(15) 0.25973(4) 0.0188(3) Uani 1 1 d . . . . .
H9 H 0.643160 0.297110 0.250350 0.023 Uiso 1 1 calc R U . . .
C10 C 0.76160(9) 0.35517(14) 0.28984(4) 0.0179(3) Uani 1 1 d . . . . .
C11 C 0.78501(9) 0.19450(15) 0.30355(4) 0.0188(3) Uani 1 1 d . U . . .
N11 N 1.02552(8) 0.33108(13) 0.46649(4) 0.0219(2) Uani 1 1 d . . . . .
O11 O 0.43040(7) 0.33495(11) 0.54250(3) 0.0269(2) Uani 1 1 d . . . . .
C12 C 0.90008(11) 0.02870(15) 0.34666(5) 0.0244(3) Uani 1 1 d . . . . .
H12A H 0.928757 -0.021261 0.321585 0.029 Uiso 1 1 calc R U . . .
H12B H 0.842277 -0.030969 0.354074 0.029 Uiso 1 1 calc R U . . .
N12 N 0.64976(8) 0.11789(12) 0.58964(4) 0.0183(2) Uani 1 1 d . . . . .
O12 O 0.45455(7) 0.15244(10) 0.59704(3) 0.0225(2) Uani 1 1 d . . . . .
C14 C 0.92865(9) 0.49360(14) 0.30150(4) 0.0176(3) Uani 1 1 d . . . . .
N14 N 0.76061(8) 0.05668(13) 0.64672(4) 0.0236(3) Uani 1 1 d . . . . .
C13 C 0.97793(11) 0.03957(16) 0.38735(5) 0.0269(3) Uani 1 1 d . . . . .
H13A H 1.000354 -0.061671 0.396609 0.040 Uiso 1 1 calc R U . . .
H13B H 0.948685 0.088742 0.411978 0.040 Uiso 1 1 calc R U . . .
H13C H 1.034795 0.098632 0.379622 0.040 Uiso 1 1 calc R U . . .
N13 N 0.71435(8) 0.17231(13) 0.62577(4) 0.0225(3) Uani 1 1 d . . . . .
C15 C 0.99198(10) 0.42026(15) 0.27321(4) 0.0218(3) Uani 1 1 d . . . . .
H15 H 0.968918 0.341235 0.253469 0.026 Uiso 1 1 calc R U . . .
C18 C 1.06258(10) 0.66441(15) 0.33371(5) 0.0234(3) Uani 1 1 d . . . . .
H18 H 1.085781 0.743989 0.353220 0.028 Uiso 1 1 calc R U . . .
C17 C 1.12532(10) 0.59325(16) 0.30627(5) 0.0246(3) Uani 1 1 d . . . . .
H17 H 1.192543 0.625183 0.307243 0.030 Uiso 1 1 calc R U . . .
C16 C 1.09035(10) 0.47257(16) 0.27652(5) 0.0242(3) Uani 1 1 d . . . . .
H16 H 1.135488 0.426975 0.258568 0.029 Uiso 1 1 calc R U . . .
C19 C 0.96182(10) 0.61221(14) 0.33116(4) 0.0190(3) Uani 1 1 d . . . . .
C21 C 1.04246(11) 0.42906(16) 0.42801(5) 0.0267(3) Uani 1 1 d . . . . .
H21A H 1.009744 0.385047 0.400286 0.040 Uiso 1 1 calc R U . . .
H21B H 1.114098 0.437622 0.425983 0.040 Uiso 1 1 calc R U . . .
H21C H 1.014729 0.529141 0.432385 0.040 Uiso 1 1 calc R U . . .
C22 C 1.11014(10) 0.24028(16) 0.48749(5) 0.0253(3) Uani 1 1 d . . . . .
H22A H 1.098541 0.133863 0.480142 0.038 Uiso 1 1 calc R U . . .
H22B H 1.116070 0.253430 0.520061 0.038 Uiso 1 1 calc R U . . .
H22C H 1.171753 0.273496 0.476155 0.038 Uiso 1 1 calc R U . . .
C23 C 0.93092(10) 0.31548(14) 0.47951(4) 0.0188(3) Uani 1 1 d . . . . .
C24 C 0.84789(10) 0.40233(15) 0.45918(4) 0.0212(3) Uani 1 1 d . . . . .
H24 H 0.856247 0.466501 0.434625 0.025 Uiso 1 1 calc R U . . .
C25 C 0.75503(10) 0.39273(15) 0.47540(4) 0.0209(3) Uani 1 1 d . . . . .
H25 H 0.702175 0.453373 0.461878 0.025 Uiso 1 1 calc R U . . .
C26 C 0.73614(10) 0.29510(14) 0.51163(4) 0.0191(3) Uani 1 1 d . . . . .
C27 C 0.81790(10) 0.20271(15) 0.53009(4) 0.0203(3) Uani 1 1 d . . . . .
H27 H 0.808203 0.133927 0.553376 0.024 Uiso 1 1 calc R U . . .
C28 C 0.91145(10) 0.21190(15) 0.51450(4) 0.0206(3) Uani 1 1 d . . . . .
H28 H 0.963508 0.148345 0.527271 0.025 Uiso 1 1 calc R U . . .
C29 C 0.63535(10) 0.29700(14) 0.52578(4) 0.0197(3) Uani 1 1 d . . . . .
H29 H 0.590661 0.362937 0.508744 0.024 Uiso 1 1 calc R U . . .
C30 C 0.59358(10) 0.22130(14) 0.55903(4) 0.0192(3) Uani 1 1 d . . . . .
C31 C 0.48519(10) 0.24473(15) 0.56476(4) 0.0200(3) Uani 1 1 d . . . . .
C32 C 0.34619(10) 0.15081(17) 0.60146(5) 0.0259(3) Uani 1 1 d . . . . .
H32A H 0.318034 0.252683 0.595658 0.031 Uiso 1 1 calc R U . . .
H32B H 0.335204 0.121178 0.632293 0.031 Uiso 1 1 calc R U . . .
C33 C 0.29402(11) 0.03850(19) 0.56771(6) 0.0345(4) Uani 1 1 d . . . . .
H33A H 0.302983 0.070454 0.537201 0.052 Uiso 1 1 calc R U . . .
H33B H 0.222822 0.035162 0.571158 0.052 Uiso 1 1 calc R U . . .
H33C H 0.323009 -0.061731 0.573238 0.052 Uiso 1 1 calc R U . . .
C34 C 0.65564(9) -0.03818(15) 0.58800(4) 0.0183(3) Uani 1 1 d . . . . .
C35 C 0.60741(10) -0.14862(15) 0.55864(5) 0.0223(3) Uani 1 1 d . . . . .
H35 H 0.560498 -0.122057 0.533999 0.027 Uiso 1 1 calc R U . . .
C36 C 0.63357(11) -0.29914(16) 0.56843(5) 0.0272(3) Uani 1 1 d . . . . .
H36 H 0.603545 -0.376467 0.549749 0.033 Uiso 1 1 calc R U . . .
C37 C 0.70429(11) -0.33952(16) 0.60581(5) 0.0281(3) Uani 1 1 d . . . . .
H37 H 0.719052 -0.442668 0.611395 0.034 Uiso 1 1 calc R U . . .
C38 C 0.75193(10) -0.23052(17) 0.63416(5) 0.0260(3) Uani 1 1 d . . . . .
H38 H 0.799069 -0.257544 0.658674 0.031 Uiso 1 1 calc R U . . .
C39 C 0.72670(10) -0.07666(16) 0.62470(4) 0.0213(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.2106(16) . ?
N1 C3 1.3644(17) . ?
N1 C2 1.4512(17) . ?
N1 C1 1.4523(17) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C14 1.3654(16) . ?
N2 N3 1.3692(15) . ?
N2 C10 1.4260(16) . ?
O2 C11 1.3408(15) . ?
O2 C12 1.4544(15) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
N3 N4 1.3017(15) . ?
C3 C4 1.4089(18) . ?
C3 C8 1.4132(18) . ?
N4 C19 1.3806(17) . ?
C4 C5 1.3712(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.4025(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.4050(18) . ?
C6 C9 1.4421(18) . ?
C7 C8 1.3745(18) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.3446(18) . ?
C9 H9 0.9300 . ?
C10 C11 1.4794(18) . ?
N11 C23 1.3573(17) . ?
N11 C22 1.4519(17) . ?
N11 C21 1.4552(17) . ?
O11 C31 1.2111(16) . ?
C12 C13 1.4934(19) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
N12 C34 1.3624(17) . ?
N12 N13 1.3724(15) . ?
N12 C30 1.4235(16) . ?
O12 C31 1.3415(16) . ?
O12 C32 1.4553(16) . ?
C14 C19 1.3915(18) . ?
C14 C15 1.4001(18) . ?
N14 N13 1.2980(16) . ?
N14 C39 1.3801(18) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 C16 1.3731(19) . ?
C15 H15 0.9300 . ?
C18 C17 1.370(2) . ?
C18 C19 1.4035(19) . ?
C18 H18 0.9300 . ?
C17 C16 1.412(2) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.4112(18) . ?
C23 C28 1.4143(18) . ?
C24 C25 1.3704(19) . ?
C24 H24 0.9300 . ?
C25 C26 1.4079(19) . ?
C25 H25 0.9300 . ?
C26 C27 1.4082(18) . ?
C26 C29 1.4421(18) . ?
C27 C28 1.3707(19) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C30 1.3490(19) . ?
C29 H29 0.9300 . ?
C30 C31 1.4779(18) . ?
C32 C33 1.506(2) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C39 1.3920(18) . ?
C34 C35 1.3985(19) . ?
C35 C36 1.378(2) . ?
C35 H35 0.9300 . ?
C36 C37 1.407(2) . ?
C36 H36 0.9300 . ?
C37 C38 1.370(2) . ?
C37 H37 0.9300 . ?
C38 C39 1.4012(19) . ?
C38 H38 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C2 120.89(11) . . ?
C3 N1 C1 120.57(11) . . ?
C2 N1 C1 117.79(11) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C14 N2 N3 109.82(10) . . ?
C14 N2 C10 127.99(11) . . ?
N3 N2 C10 121.96(10) . . ?
C11 O2 C12 115.36(10) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N4 N3 N2 108.80(10) . . ?
N1 C3 C4 121.48(12) . . ?
N1 C3 C8 121.45(12) . . ?
C4 C3 C8 117.07(12) . . ?
N3 N4 C19 108.32(10) . . ?
C5 C4 C3 120.84(12) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 122.57(12) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C5 C6 C7 116.42(12) . . ?
C5 C6 C9 117.05(11) . . ?
C7 C6 C9 126.52(12) . . ?
C8 C7 C6 121.86(12) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C3 121.22(12) . . ?
C7 C8 H8 119.4 . . ?
C3 C8 H8 119.4 . . ?
C10 C9 C6 133.55(12) . . ?
C10 C9 H9 113.2 . . ?
C6 C9 H9 113.2 . . ?
C9 C10 N2 123.99(11) . . ?
C9 C10 C11 119.31(11) . . ?
N2 C10 C11 116.69(11) . . ?
O1 C11 O2 123.63(12) . . ?
O1 C11 C10 124.23(12) . . ?
O2 C11 C10 112.14(11) . . ?
C23 N11 C22 121.20(11) . . ?
C23 N11 C21 120.39(11) . . ?
C22 N11 C21 118.16(11) . . ?
O2 C12 C13 107.68(11) . . ?
O2 C12 H12A 110.2 . . ?
C13 C12 H12A 110.2 . . ?
O2 C12 H12B 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C34 N12 N13 109.81(10) . . ?
C34 N12 C30 129.52(11) . . ?
N13 N12 C30 120.55(10) . . ?
C31 O12 C32 116.65(10) . . ?
N2 C14 C19 104.32(11) . . ?
N2 C14 C15 132.69(12) . . ?
C19 C14 C15 122.93(12) . . ?
N13 N14 C39 108.55(10) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N14 N13 N12 108.68(10) . . ?
C16 C15 C14 115.66(12) . . ?
C16 C15 H15 122.2 . . ?
C14 C15 H15 122.2 . . ?
C17 C18 C19 117.22(12) . . ?
C17 C18 H18 121.4 . . ?
C19 C18 H18 121.4 . . ?
C18 C17 C16 121.58(13) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C15 C16 C17 122.24(13) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
N4 C19 C14 108.71(11) . . ?
N4 C19 C18 130.85(12) . . ?
C14 C19 C18 120.36(12) . . ?
N11 C21 H21A 109.5 . . ?
N11 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N11 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N11 C22 H22A 109.5 . . ?
N11 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N11 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N11 C23 C24 121.78(12) . . ?
N11 C23 C28 121.24(12) . . ?
C24 C23 C28 116.98(12) . . ?
C25 C24 C23 120.43(12) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 122.89(12) . . ?
C24 C25 H25 118.6 . . ?
C26 C25 H25 118.6 . . ?
C25 C26 C27 116.31(12) . . ?
C25 C26 C29 117.41(11) . . ?
C27 C26 C29 126.27(12) . . ?
C28 C27 C26 121.48(12) . . ?
C28 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C27 C28 C23 121.75(12) . . ?
C27 C28 H28 119.1 . . ?
C23 C28 H28 119.1 . . ?
C30 C29 C26 132.20(12) . . ?
C30 C29 H29 113.9 . . ?
C26 C29 H29 113.9 . . ?
C29 C30 N12 122.74(12) . . ?
C29 C30 C31 119.83(12) . . ?
N12 C30 C31 117.43(11) . . ?
O11 C31 O12 124.16(12) . . ?
O11 C31 C30 123.96(12) . . ?
O12 C31 C30 111.87(11) . . ?
O12 C32 C33 109.36(11) . . ?
O12 C32 H32A 109.8 . . ?
C33 C32 H32A 109.8 . . ?
O12 C32 H32B 109.8 . . ?
C33 C32 H32B 109.8 . . ?
H32A C32 H32B 108.3 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N12 C34 C39 104.41(11) . . ?
N12 C34 C35 133.16(12) . . ?
C39 C34 C35 122.43(12) . . ?
C36 C35 C34 115.99(13) . . ?
C36 C35 H35 122.0 . . ?
C34 C35 H35 122.0 . . ?
C35 C36 C37 122.06(14) . . ?
C35 C36 H36 119.0 . . ?
C37 C36 H36 119.0 . . ?
C38 C37 C36 121.59(13) . . ?
C38 C37 H37 119.2 . . ?
C36 C37 H37 119.2 . . ?
C37 C38 C39 117.25(13) . . ?
C37 C38 H38 121.4 . . ?
C39 C38 H38 121.4 . . ?
N14 C39 C34 108.55(11) . . ?
N14 C39 C38 130.79(12) . . ?
C34 C39 C38 120.66(13) . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_18026_s_a
_database_code_depnum_ccdc_archive 'CCDC 1882468'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2018-11-30 deposited with the CCDC.	2019-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 N4 O2'
_chemical_formula_sum            'C19 H20 N4 O2'
_chemical_formula_weight         336.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.0183(7)
_cell_length_b                   8.3790(7)
_cell_length_c                   23.0425(18)
_cell_angle_alpha                90
_cell_angle_beta                 97.233(4)
_cell_angle_gamma                90
_cell_volume                     1727.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5522
_cell_measurement_theta_min      4.94
_cell_measurement_theta_max      68.28

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.507
_exptl_crystal_size_mid          0.453
_exptl_crystal_size_min          0.184
_exptl_absorpt_coefficient_mu    0.700
_shelx_estimated_absorpt_T_min   0.718
_shelx_estimated_absorpt_T_max   0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6638
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29779
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         4.943
_diffrn_reflns_theta_max         68.657
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3156
_reflns_number_gt                2911
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker-Nonius FR591 rotating Cu anode, MACH3 Nonius kappa 
 goniometer, Bruker APEX-II CCD detector, Kryoflex low temperature device 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0483P)²+0.7115P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3156
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0962
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.34900(10) -0.11031(11) 0.51892(4) 0.0236(2) Uani 1 1 d . . . . .
C1 C 0.55963(16) 0.87814(17) 0.70243(6) 0.0267(3) Uani 1 1 d . . . . .
H1A H 0.627718 0.967601 0.712960 0.040 Uiso 1 1 calc R U . . .
H1B H 0.574918 0.795909 0.732838 0.040 Uiso 1 1 calc R U . . .
H1C H 0.456081 0.916035 0.698938 0.040 Uiso 1 1 calc R U . . .
N1 N 0.58952(12) 0.81122(13) 0.64691(5) 0.0226(3) Uani 1 1 d . . . . .
C2 C 0.68635(15) 0.90141(16) 0.61324(6) 0.0256(3) Uani 1 1 d . . . . .
H2A H 0.648686 0.893948 0.571535 0.038 Uiso 1 1 calc R U . . .
H2B H 0.787850 0.857689 0.619988 0.038 Uiso 1 1 calc R U . . .
H2C H 0.687907 1.013495 0.625447 0.038 Uiso 1 1 calc R U . . .
N2 N 0.05756(11) 0.19134(13) 0.60524(5) 0.0196(2) Uani 1 1 d . . . . .
O2 O 0.16998(10) -0.15783(10) 0.57614(4) 0.0205(2) Uani 1 1 d . . . . .
N3 N 0.18857(11) 0.12720(12) 0.62599(4) 0.0164(2) Uani 1 1 d . . . . .
C3 C 0.54167(13) 0.66241(15) 0.63006(5) 0.0184(3) Uani 1 1 d . . . . .
N4 N 0.21786(11) 0.10730(12) 0.68388(4) 0.0185(2) Uani 1 1 d . . . . .
C4 C 0.43643(14) 0.57922(15) 0.65952(5) 0.0201(3) Uani 1 1 d . . . . .
H4 H 0.399015 0.628298 0.691886 0.024 Uiso 1 1 calc R U . . .
C7 C 0.54555(13) 0.43164(15) 0.56671(5) 0.0173(3) Uani 1 1 d . . . . .
H7 H 0.585188 0.380743 0.535189 0.021 Uiso 1 1 calc R U . . .
C6 C 0.44083(13) 0.34929(15) 0.59539(5) 0.0174(3) Uani 1 1 d . . . . .
C5 C 0.38724(14) 0.42908(15) 0.64232(5) 0.0190(3) Uani 1 1 d . . . . .
H5 H 0.315196 0.377873 0.662658 0.023 Uiso 1 1 calc R U . . .
C9 C 0.40005(13) 0.19050(15) 0.57422(5) 0.0176(3) Uani 1 1 d . . . . .
H9 H 0.459562 0.151413 0.546110 0.021 Uiso 1 1 calc R U . . .
C8 C 0.59329(13) 0.58357(15) 0.58243(5) 0.0185(3) Uani 1 1 d . . . . .
H8 H 0.662045 0.635980 0.560836 0.022 Uiso 1 1 calc R U . . .
C10 C 0.29410(13) 0.08808(15) 0.58678(5) 0.0174(3) Uani 1 1 d . . . . .
C11 C 0.27618(13) -0.06855(15) 0.55675(5) 0.0179(3) Uani 1 1 d . . . . .
C12 C 0.14184(15) -0.30932(15) 0.54564(6) 0.0223(3) Uani 1 1 d . . . . .
H12A H 0.233620 -0.375326 0.549813 0.027 Uiso 1 1 calc R U . . .
H12B H 0.110113 -0.290689 0.503481 0.027 Uiso 1 1 calc R U . . .
C13 C 0.0210(2) -0.3917(2) 0.57269(8) 0.0447(4) Uani 1 1 d . . . . .
H13A H -0.071589 -0.329693 0.565258 0.067 Uiso 1 1 calc R U . . .
H13B H 0.050281 -0.401105 0.614970 0.067 Uiso 1 1 calc R U . . .
H13C H 0.004923 -0.498344 0.555611 0.067 Uiso 1 1 calc R U . . .
C14 C 0.09296(13) 0.16554(14) 0.70321(5) 0.0178(3) Uani 1 1 d . . . . .
C15 C -0.00618(13) 0.21664(14) 0.65435(5) 0.0183(3) Uani 1 1 d . . . . .
C16 C -0.14599(15) 0.28437(16) 0.66117(6) 0.0247(3) Uani 1 1 d . . . . .
H16 H -0.213388 0.318326 0.628485 0.030 Uiso 1 1 calc R U . . .
C17 C -0.17980(15) 0.29878(16) 0.71691(7) 0.0273(3) Uani 1 1 d . . . . .
H17 H -0.273493 0.343166 0.723062 0.033 Uiso 1 1 calc R U . . .
C18 C -0.07908(16) 0.24939(16) 0.76627(6) 0.0270(3) Uani 1 1 d . . . . .
H18 H -0.107104 0.263498 0.804327 0.032 Uiso 1 1 calc R U . . .
C19 C 0.05626(15) 0.18250(16) 0.76067(6) 0.0243(3) Uani 1 1 d . . . . .
H19 H 0.122495 0.149015 0.793772 0.029 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.2074(15) . ?
C1 N1 1.4528(16) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
N1 C3 1.3599(17) . ?
N1 C2 1.4513(17) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N2 N3 1.3309(14) . ?
N2 C15 1.3490(16) . ?
O2 C11 1.3358(15) . ?
O2 C12 1.4575(15) . ?
N3 N4 1.3371(14) . ?
N3 C10 1.4304(15) . ?
C3 C8 1.4094(17) . ?
C3 C4 1.4176(17) . ?
N4 C14 1.3535(16) . ?
C4 C5 1.3756(18) . ?
C4 H4 0.9500 . ?
C7 C8 1.3776(18) . ?
C7 C6 1.4008(17) . ?
C7 H7 0.9500 . ?
C6 C5 1.4076(17) . ?
C6 C9 1.4485(17) . ?
C5 H5 0.9500 . ?
C9 C10 1.3426(17) . ?
C9 H9 0.9500 . ?
C8 H8 0.9500 . ?
C10 C11 1.4830(17) . ?
C12 C13 1.4909(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.4118(18) . ?
C14 C15 1.4131(17) . ?
C15 C16 1.4094(18) . ?
C16 C17 1.362(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.425(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3638(19) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 N1 C2 121.03(11) . . ?
C3 N1 C1 121.19(11) . . ?
C2 N1 C1 117.43(11) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N3 N2 C15 102.40(10) . . ?
C11 O2 C12 114.53(9) . . ?
N2 N3 N4 117.63(10) . . ?
N2 N3 C10 119.78(10) . . ?
N4 N3 C10 122.54(10) . . ?
N1 C3 C8 121.87(11) . . ?
N1 C3 C4 121.44(11) . . ?
C8 C3 C4 116.69(11) . . ?
N3 N4 C14 102.44(10) . . ?
C5 C4 C3 121.52(11) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C8 C7 C6 122.55(11) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C7 C6 C5 116.46(11) . . ?
C7 C6 C9 116.82(11) . . ?
C5 C6 C9 126.71(11) . . ?
C4 C5 C6 121.75(11) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C10 C9 C6 132.21(11) . . ?
C10 C9 H9 113.9 . . ?
C6 C9 H9 113.9 . . ?
C7 C8 C3 120.99(11) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C9 C10 N3 122.53(11) . . ?
C9 C10 C11 120.25(11) . . ?
N3 C10 C11 117.10(10) . . ?
O1 C11 O2 123.86(11) . . ?
O1 C11 C10 123.79(11) . . ?
O2 C11 C10 112.34(10) . . ?
O2 C12 C13 107.07(10) . . ?
O2 C12 H12A 110.3 . . ?
C13 C12 H12A 110.3 . . ?
O2 C12 H12B 110.3 . . ?
C13 C12 H12B 110.3 . . ?
H12A C12 H12B 108.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 C19 130.40(12) . . ?
N4 C14 C15 108.43(11) . . ?
C19 C14 C15 121.15(11) . . ?
N2 C15 C16 129.68(12) . . ?
N2 C15 C14 109.10(11) . . ?
C16 C15 C14 121.21(12) . . ?
C17 C16 C15 116.77(13) . . ?
C17 C16 H16 121.6 . . ?
C15 C16 H16 121.6 . . ?
C16 C17 C18 122.08(12) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C19 C18 C17 122.14(13) . . ?
C19 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C18 C19 C14 116.64(12) . . ?
C18 C19 H19 121.7 . . ?
C14 C19 H19 121.7 . . ?

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_18088_a
_database_code_depnum_ccdc_archive 'CCDC 1882467'
loop_
_audit_author_name
_audit_author_address
'Gabriel Alejandro Valdivia Berroeta'
;Brigham Young university
United States of America
;
_audit_update_record             
;
2018-11-30 deposited with the CCDC.	2019-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 N4 O3'
_chemical_formula_sum            'C21 H22 N4 O3'
_chemical_formula_weight         378.42

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

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

_cell_length_a                   17.5573(10)
_cell_length_b                   6.3237(4)
_cell_length_c                   33.7271(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3744.6(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9858
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      68.30

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.356
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.115
_exptl_absorpt_coefficient_mu    0.749
_shelx_estimated_absorpt_T_min   0.776
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6495
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Bruker-Nonius FR591 Cu rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            62898
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.620
_diffrn_reflns_theta_max         68.623
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6840
_reflns_number_gt                6508
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.963
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²+0.9980P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.5(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6840
_refine_ls_number_parameters     508
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0958
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.66296(10) 0.3687(3) 0.46942(6) 0.0273(5) Uani 1 1 d . . . . .
N1 N 0.81990(12) 0.2770(4) 0.45652(6) 0.0201(5) Uani 1 1 d . . . . .
C1 C 0.71968(16) 0.4574(5) 0.49420(9) 0.0272(6) Uani 1 1 d . . . . .
H1A H 0.726728 0.365941 0.517748 0.033 Uiso 1 1 calc R U . . .
H1AB H 0.702590 0.598033 0.503520 0.033 Uiso 1 1 calc R U . . .
O2 O 1.25256(11) 0.0988(3) 0.31603(6) 0.0298(5) Uani 1 1 d . . . . .
N2 N 1.11134(12) -0.0197(4) 0.34175(6) 0.0180(5) Uani 1 1 d . . . . .
C2 C 0.79492(15) 0.4803(5) 0.47279(9) 0.0268(6) Uani 1 1 d . . . . .
H2A H 0.789454 0.584201 0.451011 0.032 Uiso 1 1 calc R U . . .
H2AB H 0.833895 0.534259 0.491439 0.032 Uiso 1 1 calc R U . . .
C3 C 0.68631(16) 0.1628(5) 0.45792(9) 0.0281(6) Uani 1 1 d . . . . .
H3A H 0.645777 0.096631 0.441727 0.034 Uiso 1 1 calc R U . . .
H3AB H 0.693848 0.074837 0.481879 0.034 Uiso 1 1 calc R U . . .
O3 O 1.27191(10) 0.3008(3) 0.37023(5) 0.0244(4) Uani 1 1 d . . . . .
N3 N 1.11616(13) -0.2267(4) 0.35323(7) 0.0233(5) Uani 1 1 d . . . . .
C4 C 0.75930(15) 0.1691(5) 0.43436(9) 0.0278(6) Uani 1 1 d . . . . .
H4A H 0.775581 0.022923 0.428143 0.033 Uiso 1 1 calc R U . . .
H4AB H 0.750333 0.243960 0.409009 0.033 Uiso 1 1 calc R U . . .
N4 N 1.07072(14) -0.3390(4) 0.33115(7) 0.0259(5) Uani 1 1 d . . . . .
C5 C 0.89305(14) 0.2706(4) 0.44002(7) 0.0186(5) Uani 1 1 d . . . . .
C6 C 0.91776(16) 0.0959(5) 0.41787(8) 0.0213(6) Uani 1 1 d . . . . .
H6 H 0.883885 -0.019255 0.413846 0.026 Uiso 1 1 calc R U . . .
C7 C 0.99016(16) 0.0867(5) 0.40170(8) 0.0225(6) Uani 1 1 d . . . . .
H7 H 1.004924 -0.034828 0.387036 0.027 Uiso 1 1 calc R U . . .
C8 C 1.04171(15) 0.2516(5) 0.40648(8) 0.0197(5) Uani 1 1 d . . . . .
C9 C 1.01814(15) 0.4228(5) 0.42932(8) 0.0235(6) Uani 1 1 d . . . . .
H9 H 1.052824 0.535530 0.433897 0.028 Uiso 1 1 calc R U . . .
C10 C 0.94564(15) 0.4346(5) 0.44566(8) 0.0232(6) Uani 1 1 d . . . . .
H10 H 0.931562 0.555033 0.460822 0.028 Uiso 1 1 calc R U . . .
C11 C 1.11891(15) 0.2617(4) 0.39003(8) 0.0194(6) Uani 1 1 d . . . . .
H11 H 1.150368 0.369749 0.400754 0.023 Uiso 1 1 calc R U . . .
O11 O 0.57496(11) 0.1086(4) 0.53407(6) 0.0280(5) Uani 1 1 d . . . . .
N11 N 0.41938(12) 0.2174(4) 0.54680(6) 0.0219(5) Uani 1 1 d . . . . .
C12 C 1.15183(14) 0.1414(4) 0.36211(8) 0.0198(6) Uani 1 1 d . . . . .
O12 O -0.01130(12) 0.4629(4) 0.68573(6) 0.0337(5) Uani 1 1 d . . . . .
N12 N 0.13144(13) 0.5631(4) 0.66027(6) 0.0193(5) Uani 1 1 d . . . . .
C14 C 1.03541(15) -0.2048(4) 0.30448(8) 0.0192(5) Uani 1 1 d . . . . .
N14 N 0.15312(15) 0.8863(4) 0.67877(7) 0.0282(6) Uani 1 1 d . . . . .
C13 C 1.06120(14) 0.0001(4) 0.31104(7) 0.0173(5) Uani 1 1 d . . . . .
O13 O -0.02985(11) 0.2362(4) 0.63476(7) 0.0335(5) Uani 1 1 d . . . . .
N13 N 0.11268(14) 0.7714(4) 0.65470(7) 0.0253(5) Uani 1 1 d . . . . .
C16 C 0.95703(17) -0.0778(5) 0.25293(9) 0.0287(7) Uani 1 1 d . . . . .
H16 H 0.920342 -0.100323 0.232660 0.034 Uiso 1 1 calc R U . . .
C15 C 0.98220(16) -0.2468(5) 0.27451(8) 0.0247(6) Uani 1 1 d . . . . .
H15 H 0.964482 -0.386144 0.269451 0.030 Uiso 1 1 calc R U . . .
C18 C 1.03662(17) 0.1742(5) 0.28897(8) 0.0266(6) Uani 1 1 d . . . . .
H18 H 1.054881 0.313360 0.293678 0.032 Uiso 1 1 calc R U . . .
C17 C 0.98402(19) 0.1293(5) 0.25989(9) 0.0323(7) Uani 1 1 d . . . . .
H17 H 0.965203 0.241628 0.243948 0.039 Uiso 1 1 calc R U . . .
C19 C 1.23001(15) 0.1766(4) 0.34659(8) 0.0206(5) Uani 1 1 d . . . . .
C20 C 1.34768(15) 0.3578(5) 0.35567(8) 0.0262(6) Uani 1 1 d . . . . .
H20A H 1.368466 0.240224 0.339590 0.031 Uiso 1 1 calc R U . . .
H20B H 1.382270 0.381051 0.378439 0.031 Uiso 1 1 calc R U . . .
C21 C 1.34405(19) 0.5552(5) 0.33086(10) 0.0350(7) Uani 1 1 d . . . . .
H21A H 1.395786 0.607019 0.325879 0.053 Uiso 1 1 calc R U . . .
H21B H 1.314894 0.663839 0.344977 0.053 Uiso 1 1 calc R U . . .
H21C H 1.319114 0.523503 0.305552 0.053 Uiso 1 1 calc R U . . .
C31 C 0.51709(17) 0.0249(5) 0.50939(9) 0.0295(7) Uani 1 1 d . . . . .
H31A H 0.532388 -0.117479 0.500131 0.035 Uiso 1 1 calc R U . . .
H31B H 0.510985 0.116568 0.485814 0.035 Uiso 1 1 calc R U . . .
C32 C 0.44208(16) 0.0096(5) 0.53098(9) 0.0280(7) Uani 1 1 d . . . . .
H32A H 0.402368 -0.042607 0.512582 0.034 Uiso 1 1 calc R U . . .
H32B H 0.446669 -0.092929 0.553041 0.034 Uiso 1 1 calc R U . . .
C33 C 0.55454(16) 0.3165(5) 0.54536(9) 0.0297(7) Uani 1 1 d . . . . .
H33A H 0.547907 0.404502 0.521327 0.036 Uiso 1 1 calc R U . . .
H33B H 0.596069 0.379110 0.561380 0.036 Uiso 1 1 calc R U . . .
C34 C 0.48149(15) 0.3182(5) 0.56920(9) 0.0291(7) Uani 1 1 d . . . . .
H34A H 0.489439 0.241513 0.594460 0.035 Uiso 1 1 calc R U . . .
H34B H 0.467350 0.465865 0.575579 0.035 Uiso 1 1 calc R U . . .
C35 C 0.34637(15) 0.2319(4) 0.56344(8) 0.0210(6) Uani 1 1 d . . . . .
C36 C 0.32345(15) 0.4163(5) 0.58380(8) 0.0215(6) Uani 1 1 d . . . . .
H36 H 0.358114 0.530991 0.586136 0.026 Uiso 1 1 calc R U . . .
C37 C 0.25178(16) 0.4340(4) 0.60039(7) 0.0206(6) Uani 1 1 d . . . . .
H37 H 0.238294 0.559966 0.614025 0.025 Uiso 1 1 calc R U . . .
C38 C 0.19836(15) 0.2686(4) 0.59746(7) 0.0191(5) Uani 1 1 d . . . . .
C39 C 0.22055(16) 0.0893(5) 0.57630(8) 0.0239(6) Uani 1 1 d . . . . .
H39 H 0.185222 -0.023246 0.573193 0.029 Uiso 1 1 calc R U . . .
C40 C 0.29239(15) 0.0699(5) 0.55965(8) 0.0244(6) Uani 1 1 d . . . . .
H40 H 0.305207 -0.054913 0.545470 0.029 Uiso 1 1 calc R U . . .
C41 C 0.12192(15) 0.2691(4) 0.61452(8) 0.0199(6) Uani 1 1 d . . . . .
H41 H 0.089550 0.159201 0.605295 0.024 Uiso 1 1 calc R U . . .
C42 C 0.09001(15) 0.3997(4) 0.64111(8) 0.0197(6) Uani 1 1 d . . . . .
C43 C 0.18479(15) 0.5457(4) 0.68959(8) 0.0199(6) Uani 1 1 d . . . . .
C44 C 0.19848(16) 0.7524(4) 0.70144(8) 0.0220(6) Uani 1 1 d . . . . .
C45 C 0.25056(19) 0.7974(5) 0.73191(8) 0.0302(7) Uani 1 1 d . . . . .
H45 H 0.258766 0.937600 0.741070 0.036 Uiso 1 1 calc R U . . .
C46 C 0.28876(18) 0.6294(6) 0.74767(9) 0.0320(7) Uani 1 1 d . . . . .
H46 H 0.325161 0.654039 0.767989 0.038 Uiso 1 1 calc R U . . .
C47 C 0.27592(18) 0.4203(5) 0.73476(10) 0.0322(7) Uani 1 1 d . . . . .
H47 H 0.304432 0.308605 0.746348 0.039 Uiso 1 1 calc R U . . .
C48 C 0.22310(16) 0.3735(5) 0.70576(9) 0.0263(6) Uani 1 1 d . . . . .
H48 H 0.213503 0.232570 0.697369 0.032 Uiso 1 1 calc R U . . .
C49 C 0.01140(16) 0.3713(5) 0.65691(8) 0.0242(6) Uani 1 1 d . . . . .
C50 C -0.10479(18) 0.1747(6) 0.64944(12) 0.0424(9) Uani 1 1 d . . . . .
H50A H -0.125131 0.288022 0.666703 0.051 Uiso 1 1 calc R U . . .
H50B H -0.140074 0.157239 0.626774 0.051 Uiso 1 1 calc R U . . .
C51 C -0.1009(2) -0.0225(6) 0.67175(14) 0.0507(10) Uani 1 1 d . . . . .
H51A H -0.152627 -0.074416 0.676796 0.076 Uiso 1 1 calc R U . . .
H51B H -0.074986 0.002467 0.697046 0.076 Uiso 1 1 calc R U . . .
H51C H -0.072616 -0.127996 0.656406 0.076 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.416(4) . ?
O1 C3 1.419(4) . ?
N1 C5 1.400(3) . ?
N1 C2 1.465(4) . ?
N1 C4 1.468(3) . ?
C1 C2 1.513(4) . ?
C1 H1A 0.9900 . ?
C1 H1AB 0.9900 . ?
O2 C19 1.209(3) . ?
N2 C13 1.365(3) . ?
N2 N3 1.368(3) . ?
N2 C12 1.420(3) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.508(4) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
O3 C19 1.339(3) . ?
O3 C20 1.463(3) . ?
N3 N4 1.302(3) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
N4 C14 1.383(4) . ?
C5 C10 1.401(4) . ?
C5 C6 1.403(4) . ?
C6 C7 1.384(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(4) . ?
C8 C11 1.466(4) . ?
C9 C10 1.389(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.342(4) . ?
C11 H11 0.9500 . ?
O11 C33 1.415(4) . ?
O11 C31 1.416(4) . ?
N11 C35 1.402(3) . ?
N11 C34 1.472(3) . ?
N11 C32 1.474(4) . ?
C12 C19 1.486(4) . ?
O12 C49 1.200(4) . ?
N12 C43 1.366(4) . ?
N12 N13 1.371(3) . ?
N12 C42 1.419(4) . ?
C14 C13 1.390(4) . ?
C14 C15 1.402(4) . ?
N14 N13 1.301(4) . ?
N14 C44 1.392(4) . ?
C13 C18 1.397(4) . ?
O13 C49 1.346(4) . ?
O13 C50 1.459(4) . ?
C16 C15 1.366(4) . ?
C16 C17 1.413(5) . ?
C16 H16 0.9500 . ?
C15 H15 0.9500 . ?
C18 C17 1.377(4) . ?
C18 H18 0.9500 . ?
C17 H17 0.9500 . ?
C20 C21 1.505(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C31 C32 1.508(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.514(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C40 1.401(4) . ?
C35 C36 1.412(4) . ?
C36 C37 1.382(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.408(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.395(4) . ?
C38 C41 1.460(4) . ?
C39 C40 1.386(4) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C42 1.342(4) . ?
C41 H41 0.9500 . ?
C42 C49 1.490(4) . ?
C43 C44 1.388(4) . ?
C43 C48 1.392(4) . ?
C44 C45 1.405(4) . ?
C45 C46 1.364(5) . ?
C45 H45 0.9500 . ?
C46 C47 1.410(5) . ?
C46 H46 0.9500 . ?
C47 C48 1.380(4) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
C50 C51 1.458(5) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 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
C1 O1 C3 108.8(2) . . ?
C5 N1 C2 116.7(2) . . ?
C5 N1 C4 116.7(2) . . ?
C2 N1 C4 112.4(2) . . ?
O1 C1 C2 111.7(2) . . ?
O1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
O1 C1 H1AB 109.3 . . ?
C2 C1 H1AB 109.3 . . ?
H1A C1 H1AB 107.9 . . ?
C13 N2 N3 110.1(2) . . ?
C13 N2 C12 128.6(2) . . ?
N3 N2 C12 121.3(2) . . ?
N1 C2 C1 110.9(3) . . ?
N1 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
N1 C2 H2AB 109.5 . . ?
C1 C2 H2AB 109.5 . . ?
H2A C2 H2AB 108.1 . . ?
O1 C3 C4 111.4(3) . . ?
O1 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
O1 C3 H3AB 109.3 . . ?
C4 C3 H3AB 109.3 . . ?
H3A C3 H3AB 108.0 . . ?
C19 O3 C20 116.4(2) . . ?
N4 N3 N2 108.8(2) . . ?
N1 C4 C3 111.1(2) . . ?
N1 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
N1 C4 H4AB 109.4 . . ?
C3 C4 H4AB 109.4 . . ?
H4A C4 H4AB 108.0 . . ?
N3 N4 C14 108.2(2) . . ?
N1 C5 C10 121.9(2) . . ?
N1 C5 C6 121.2(2) . . ?
C10 C5 C6 116.8(2) . . ?
C7 C6 C5 121.8(3) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 121.4(3) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C9 117.0(2) . . ?
C7 C8 C11 126.2(3) . . ?
C9 C8 C11 116.8(2) . . ?
C10 C9 C8 122.3(3) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C5 120.7(3) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C12 C11 C8 129.7(3) . . ?
C12 C11 H11 115.1 . . ?
C8 C11 H11 115.1 . . ?
C33 O11 C31 108.9(2) . . ?
C35 N11 C34 116.3(2) . . ?
C35 N11 C32 116.8(2) . . ?
C34 N11 C32 111.8(2) . . ?
C11 C12 N2 122.1(2) . . ?
C11 C12 C19 124.1(2) . . ?
N2 C12 C19 113.6(2) . . ?
C43 N12 N13 110.0(2) . . ?
C43 N12 C42 128.5(2) . . ?
N13 N12 C42 120.9(2) . . ?
N4 C14 C13 108.8(2) . . ?
N4 C14 C15 130.6(3) . . ?
C13 C14 C15 120.5(3) . . ?
N13 N14 C44 108.4(2) . . ?
N2 C13 C14 104.2(2) . . ?
N2 C13 C18 132.5(3) . . ?
C14 C13 C18 123.3(2) . . ?
C49 O13 C50 117.8(3) . . ?
N14 N13 N12 108.7(2) . . ?
C15 C16 C17 121.9(3) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C16 C15 C14 116.8(3) . . ?
C16 C15 H15 121.6 . . ?
C14 C15 H15 121.6 . . ?
C17 C18 C13 115.1(3) . . ?
C17 C18 H18 122.4 . . ?
C13 C18 H18 122.4 . . ?
C18 C17 C16 122.3(3) . . ?
C18 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
O2 C19 O3 124.5(2) . . ?
O2 C19 C12 122.8(3) . . ?
O3 C19 C12 112.7(2) . . ?
O3 C20 C21 110.7(2) . . ?
O3 C20 H20A 109.5 . . ?
C21 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O11 C31 C32 111.5(2) . . ?
O11 C31 H31A 109.3 . . ?
C32 C31 H31A 109.3 . . ?
O11 C31 H31B 109.3 . . ?
C32 C31 H31B 109.3 . . ?
H31A C31 H31B 108.0 . . ?
N11 C32 C31 110.7(3) . . ?
N11 C32 H32A 109.5 . . ?
C31 C32 H32A 109.5 . . ?
N11 C32 H32B 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
O11 C33 C34 111.3(3) . . ?
O11 C33 H33A 109.4 . . ?
C34 C33 H33A 109.4 . . ?
O11 C33 H33B 109.4 . . ?
C34 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
N11 C34 C33 110.6(2) . . ?
N11 C34 H34A 109.5 . . ?
C33 C34 H34A 109.5 . . ?
N11 C34 H34B 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 108.1 . . ?
C40 C35 N11 122.3(2) . . ?
C40 C35 C36 117.1(2) . . ?
N11 C35 C36 120.6(2) . . ?
C37 C36 C35 121.5(3) . . ?
C37 C36 H36 119.2 . . ?
C35 C36 H36 119.2 . . ?
C36 C37 C38 121.2(3) . . ?
C36 C37 H37 119.4 . . ?
C38 C37 H37 119.4 . . ?
C39 C38 C37 117.0(2) . . ?
C39 C38 C41 117.4(3) . . ?
C37 C38 C41 125.7(2) . . ?
C40 C39 C38 122.2(3) . . ?
C40 C39 H39 118.9 . . ?
C38 C39 H39 118.9 . . ?
C39 C40 C35 120.9(3) . . ?
C39 C40 H40 119.5 . . ?
C35 C40 H40 119.5 . . ?
C42 C41 C38 130.4(3) . . ?
C42 C41 H41 114.8 . . ?
C38 C41 H41 114.8 . . ?
C41 C42 N12 122.6(2) . . ?
C41 C42 C49 123.5(3) . . ?
N12 C42 C49 113.6(2) . . ?
N12 C43 C44 104.6(2) . . ?
N12 C43 C48 132.7(3) . . ?
C44 C43 C48 122.7(3) . . ?
C43 C44 N14 108.4(2) . . ?
C43 C44 C45 121.0(3) . . ?
N14 C44 C45 130.6(3) . . ?
C46 C45 C44 116.6(3) . . ?
C46 C45 H45 121.7 . . ?
C44 C45 H45 121.7 . . ?
C45 C46 C47 122.1(3) . . ?
C45 C46 H46 119.0 . . ?
C47 C46 H46 119.0 . . ?
C48 C47 C46 121.8(3) . . ?
C48 C47 H47 119.1 . . ?
C46 C47 H47 119.1 . . ?
C47 C48 C43 115.8(3) . . ?
C47 C48 H48 122.1 . . ?
C43 C48 H48 122.1 . . ?
O12 C49 O13 125.3(3) . . ?
O12 C49 C42 122.6(3) . . ?
O13 C49 C42 112.1(2) . . ?
C51 C50 O13 111.2(3) . . ?
C51 C50 H50A 109.4 . . ?
O13 C50 H50A 109.4 . . ?
C51 C50 H50B 109.4 . . ?
O13 C50 H50B 109.4 . . ?
H50A C50 H50B 108.0 . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.041


_exptl_crystal_preparation       Luminescent
