# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_mo_023WB46_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1989719'
loop_
_audit_author_name
_audit_author_address
'Merce Font Bardia'
;University of Barcelona
Spain
;
_audit_update_record             
;
2020-03-11 deposited with the CCDC.	2020-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 N4 O'
_chemical_formula_weight         302.33

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   27.7141(13)
_cell_length_b                   6.4562(3)
_cell_length_c                   20.6251(10)
_cell_angle_alpha                90
_cell_angle_beta                 128.1800(10)
_cell_angle_gamma                90
_cell_volume                     2900.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7790
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      27.47

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.292
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6825
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24789
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.947
_diffrn_reflns_theta_max         27.605
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3348
_reflns_number_gt                2631
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0807P)²+2.6312P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3348
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1476
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.29346(6) 0.8892(2) 0.58507(8) 0.0331(3) Uani 1 1 d . . . . .
N1 N 0.32782(6) 0.7044(2) 0.52798(9) 0.0246(3) Uani 1 1 d . . . . .
H1N H 0.294315 0.628276 0.500476 0.030 Uiso 1 1 calc R U . . .
N2 N 0.37314(6) 0.5226(2) 0.47322(8) 0.0218(3) Uani 1 1 d . . . . .
N3 N 0.42539(6) 0.5497(2) 0.47790(8) 0.0227(3) Uani 1 1 d . . . . .
N4 N 0.50789(7) 0.7858(2) 0.54386(10) 0.0293(3) Uani 1 1 d . . . . .
H4NA H 0.5254(10) 0.705(4) 0.5282(13) 0.036(6) Uiso 1 1 d . . . . .
H4NB H 0.5215(14) 0.917(5) 0.5636(18) 0.069(8) Uiso 1 1 d . . . . .
C1 C 0.42307(8) 1.3272(3) 0.68974(12) 0.0349(4) Uani 1 1 d . . . . .
H1 H 0.430397 1.364787 0.651974 0.042 Uiso 1 1 calc R U . . .
C2 C 0.43355(9) 1.4701(3) 0.74808(14) 0.0457(6) Uani 1 1 d . . . . .
H2 H 0.447846 1.605322 0.749813 0.055 Uiso 1 1 calc R U . . .
C3 C 0.42317(9) 1.4154(4) 0.80316(14) 0.0469(6) Uani 1 1 d . . . . .
H3 H 0.430685 1.513061 0.842937 0.056 Uiso 1 1 calc R U . . .
C4 C 0.40196(9) 1.2202(4) 0.80103(12) 0.0418(5) Uani 1 1 d . . . . .
H4 H 0.394960 1.183850 0.839234 0.050 Uiso 1 1 calc R U . . .
C5 C 0.39088(8) 1.0769(3) 0.74302(11) 0.0340(4) Uani 1 1 d . . . . .
H5 H 0.375822 0.943094 0.741170 0.041 Uiso 1 1 calc R U . . .
C6 C 0.40184(7) 1.1292(3) 0.68707(10) 0.0280(4) Uani 1 1 d . . . . .
C7 C 0.39258(7) 0.9752(3) 0.62695(10) 0.0246(4) Uani 1 1 d . . . . .
C8 C 0.43366(7) 0.9490(3) 0.61145(10) 0.0237(3) Uani 1 1 d . . . . .
H8 H 0.469169 1.034086 0.638381 0.028 Uiso 1 1 calc R U . . .
C9 C 0.42300(7) 0.7949(2) 0.55519(10) 0.0214(3) Uani 1 1 d . . . . .
C10 C 0.37132(7) 0.6710(2) 0.51789(9) 0.0213(3) Uani 1 1 d . . . . .
C11 C 0.33566(7) 0.8563(3) 0.58086(10) 0.0263(4) Uani 1 1 d . . . . .
C12 C 0.45435(7) 0.7127(2) 0.52625(10) 0.0207(3) Uani 1 1 d . . . . .
C13 C 0.33313(7) 0.3532(2) 0.42769(10) 0.0219(3) Uani 1 1 d . . . . .
C14 C 0.29856(8) 0.2663(3) 0.44864(11) 0.0269(4) Uani 1 1 d . . . . .
H14 H 0.301878 0.318474 0.494318 0.032 Uiso 1 1 calc R U . . .
C15 C 0.25922(8) 0.1031(3) 0.40258(12) 0.0310(4) Uani 1 1 d . . . . .
H15 H 0.234379 0.047124 0.415515 0.037 Uiso 1 1 calc R U . . .
C16 C 0.25584(9) 0.0211(3) 0.33789(12) 0.0331(4) Uani 1 1 d . . . . .
H16 H 0.229140 -0.091749 0.306826 0.040 Uiso 1 1 calc R U . . .
C17 C 0.29180(9) 0.1050(3) 0.31873(11) 0.0338(4) Uani 1 1 d . . . . .
H17 H 0.290166 0.047123 0.275057 0.041 Uiso 1 1 calc R U . . .
C18 C 0.32999(8) 0.2720(3) 0.36256(11) 0.0284(4) Uani 1 1 d . . . . .
H18 H 0.353805 0.330567 0.348391 0.034 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 1.243(2) . ?
N1 C10 1.361(2) . ?
N1 C11 1.380(2) . ?
N1 H1N 0.8800 . ?
N2 C10 1.352(2) . ?
N2 N3 1.4013(18) . ?
N2 C13 1.421(2) . ?
N3 C12 1.325(2) . ?
N4 C12 1.375(2) . ?
N4 H4NA 0.90(2) . ?
N4 H4NB 0.91(3) . ?
C1 C6 1.394(3) . ?
C1 C2 1.397(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.483(2) . ?
C7 C8 1.370(2) . ?
C7 C11 1.459(2) . ?
C8 C9 1.414(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(2) . ?
C9 C12 1.427(2) . ?
C13 C14 1.390(2) . ?
C13 C18 1.394(2) . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(2) . ?
C17 H17 0.9500 . ?
C18 H18 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
C10 N1 C11 120.77(13) . . ?
C10 N1 H1N 119.6 . . ?
C11 N1 H1N 119.6 . . ?
C10 N2 N3 109.69(12) . . ?
C10 N2 C13 130.78(13) . . ?
N3 N2 C13 119.51(12) . . ?
C12 N3 N2 105.69(12) . . ?
C12 N4 H4NA 116.2(14) . . ?
C12 N4 H4NB 121.1(19) . . ?
H4NA N4 H4NB 122(2) . . ?
C6 C1 C2 119.8(2) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.62(18) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.24(17) . . ?
C1 C6 C7 119.90(17) . . ?
C5 C6 C7 120.85(17) . . ?
C8 C7 C11 120.20(15) . . ?
C8 C7 C6 122.59(15) . . ?
C11 C7 C6 117.14(14) . . ?
C7 C8 C9 119.72(15) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 118.81(14) . . ?
C10 C9 C12 103.91(14) . . ?
C8 C9 C12 137.13(15) . . ?
N2 C10 N1 128.78(14) . . ?
N2 C10 C9 109.05(14) . . ?
N1 C10 C9 122.17(14) . . ?
O1 C11 N1 118.75(15) . . ?
O1 C11 C7 123.35(15) . . ?
N1 C11 C7 117.86(14) . . ?
N3 C12 N4 121.62(14) . . ?
N3 C12 C9 111.61(14) . . ?
N4 C12 C9 126.77(15) . . ?
C14 C13 C18 120.23(15) . . ?
C14 C13 N2 120.77(14) . . ?
C18 C13 N2 118.99(15) . . ?
C15 C14 C13 119.69(15) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 120.49(16) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.49(16) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 120.75(17) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C13 119.30(16) . . ?
C17 C18 H18 120.4 . . ?
C13 C18 H18 120.4 . . ?

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_028XB107_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1989723'
loop_
_audit_author_name
_audit_author_address
'Merce Font Bardia'
;University of Barcelona
Spain
;
_audit_update_record             
;
2020-03-11 deposited with the CCDC.	2020-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N4 O3'
_chemical_formula_sum            'C14 H16 N4 O3'
_chemical_formula_weight         288.31

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

_space_group_crystal_system      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                   10.0257(7)
_cell_length_b                   13.4533(8)
_cell_length_c                   10.8045(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.456(2)
_cell_angle_gamma                90
_cell_volume                     1382.34(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      34.26

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.122
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5755
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30489
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.498
_diffrn_reflns_theta_max         34.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5780
_reflns_number_gt                4178
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0681P)²+0.8033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5780
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1615
_refine_ls_wR_factor_gt          0.1301
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.55802(11) 0.44090(7) 0.38311(11) 0.0262(2) Uani 1 1 d . . . . .
O2 O 0.02284(12) 0.10484(7) 0.59011(11) 0.0261(2) Uani 1 1 d . . . . .
N1 N 0.39708(11) 0.38201(8) 0.47029(11) 0.0190(2) Uani 1 1 d . . . . .
H1 H 0.399271 0.437681 0.513646 0.023 Uiso 1 1 calc R U . . .
N2 N 0.21298(11) 0.31600(7) 0.54143(11) 0.01664(19) Uani 1 1 d . . . . .
N3 N 0.18981(13) 0.05716(8) 0.44729(12) 0.0221(2) Uani 1 1 d . . . . .
H3A H 0.235838 0.019939 0.407478 0.027 Uiso 1 1 calc R U . . .
H3B H 0.123063 0.030914 0.473653 0.027 Uiso 1 1 calc R U . . .
N4 N 0.15599(11) 0.21947(7) 0.53227(11) 0.01618(19) Uani 1 1 d . . . . .
C1 C 0.47944(13) 0.37246(9) 0.39219(13) 0.0188(2) Uani 1 1 d . . . . .
C2 C 0.46683(14) 0.27833(9) 0.31306(13) 0.0197(2) Uani 1 1 d . . . . .
H2A H 0.555512 0.268404 0.292733 0.024 Uiso 1 1 calc R U . . .
H2AB H 0.390548 0.287191 0.229283 0.024 Uiso 1 1 calc R U . . .
C3 C 0.43641(13) 0.18392(9) 0.38005(13) 0.0195(2) Uani 1 1 d . . . . .
H3 H 0.403192 0.130118 0.313522 0.023 Uiso 1 1 calc R U . . .
C4 C 0.32107(12) 0.20982(9) 0.43494(13) 0.0172(2) Uani 1 1 d . . . . .
C5 C 0.30956(12) 0.30514(9) 0.48257(12) 0.0160(2) Uani 1 1 d . . . . .
C6 C 0.22150(12) 0.15422(9) 0.46784(12) 0.0169(2) Uani 1 1 d . . . . .
C7 C 0.05118(13) 0.19272(9) 0.58559(13) 0.0177(2) Uani 1 1 d . . . . .
C8 C -0.02425(13) 0.27015(9) 0.63628(12) 0.0177(2) Uani 1 1 d . . . . .
C9 C -0.07841(13) 0.23847(10) 0.73428(13) 0.0214(2) Uani 1 1 d . . . . .
H9 H -0.061788 0.172479 0.766812 0.026 Uiso 1 1 calc R U . . .
C10 C -0.15644(14) 0.30347(11) 0.78397(14) 0.0245(3) Uani 1 1 d . . . . .
H10 H -0.192418 0.282018 0.850958 0.029 Uiso 1 1 calc R U . . .
C11 C -0.18197(15) 0.39995(12) 0.73579(15) 0.0266(3) Uani 1 1 d . . . . .
H11 H -0.233879 0.444681 0.770950 0.032 Uiso 1 1 calc R U . . .
C12 C -0.13151(15) 0.43078(11) 0.63625(16) 0.0255(3) Uani 1 1 d . . . . .
H12 H -0.150524 0.496301 0.602461 0.031 Uiso 1 1 calc R U . . .
C13 C -0.05313(13) 0.36621(10) 0.58559(14) 0.0207(2) Uani 1 1 d . . . . .
H13 H -0.019517 0.387394 0.516982 0.025 Uiso 1 1 calc R U . . .
C14 C 0.56798(16) 0.14827(12) 0.48775(17) 0.0288(3) Uani 1 1 d . . . . .
H14A H 0.638441 0.125710 0.448518 0.043 Uiso 1 1 calc R U . . .
H14B H 0.542895 0.093170 0.535448 0.043 Uiso 1 1 calc R U . . .
H14C H 0.606664 0.203144 0.548088 0.043 Uiso 1 1 calc R U . . .
O1W O 0.78597(12) 0.49206(8) 0.30086(11) 0.0263(2) Uani 1 1 d . . . . .
H1WA H 0.706(3) 0.463(2) 0.322(3) 0.071(9) Uiso 1 1 d . . . . .
H1WB H 0.797(3) 0.552(2) 0.347(3) 0.062(8) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2357(15) . ?
O2 C7 1.2206(15) . ?
N1 C1 1.3606(16) . ?
N1 C5 1.3895(15) . ?
N1 H1 0.8800 . ?
N2 C5 1.3241(15) . ?
N2 N4 1.4096(14) . ?
N3 C6 1.3456(16) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 C7 1.3960(15) . ?
N4 C6 1.4057(15) . ?
C1 C2 1.5108(18) . ?
C2 C3 1.5394(18) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.4982(17) . ?
C3 C14 1.534(2) . ?
C3 H3 1.0000 . ?
C4 C6 1.3809(16) . ?
C4 C5 1.4002(16) . ?
C7 C8 1.4897(17) . ?
C8 C13 1.3977(18) . ?
C8 C9 1.4005(18) . ?
C9 C10 1.3896(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3943(19) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O1W H1WA 0.98(3) . ?
O1W H1WB 0.94(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 120.97(10) . . ?
C1 N1 H1 119.5 . . ?
C5 N1 H1 119.5 . . ?
C5 N2 N4 101.92(9) . . ?
C6 N3 H3A 120.0 . . ?
C6 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C7 N4 C6 125.04(10) . . ?
C7 N4 N2 123.35(10) . . ?
C6 N4 N2 111.56(9) . . ?
O1 C1 N1 120.42(12) . . ?
O1 C1 C2 121.39(11) . . ?
N1 C1 C2 118.14(10) . . ?
C1 C2 C3 114.77(11) . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2AB 108.6 . . ?
C3 C2 H2AB 108.6 . . ?
H2A C2 H2AB 107.6 . . ?
C4 C3 C14 111.02(11) . . ?
C4 C3 C2 106.68(10) . . ?
C14 C3 C2 111.34(11) . . ?
C4 C3 H3 109.3 . . ?
C14 C3 H3 109.3 . . ?
C2 C3 H3 109.3 . . ?
C6 C4 C5 104.54(10) . . ?
C6 C4 C3 133.43(11) . . ?
C5 C4 C3 121.48(10) . . ?
N2 C5 N1 122.94(11) . . ?
N2 C5 C4 115.81(10) . . ?
N1 C5 C4 121.24(10) . . ?
N3 C6 C4 129.44(11) . . ?
N3 C6 N4 124.39(11) . . ?
C4 C6 N4 106.17(10) . . ?
O2 C7 N4 118.77(11) . . ?
O2 C7 C8 120.73(11) . . ?
N4 C7 C8 120.50(10) . . ?
C13 C8 C9 119.72(12) . . ?
C13 C8 C7 124.66(11) . . ?
C9 C8 C7 115.38(11) . . ?
C10 C9 C8 120.07(13) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.12(13) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.95(13) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.44(13) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 119.66(12) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H1WA O1W H1WB 101(2) . . ?

_refine_diff_density_max         0.528
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.071

