# Electronic Supplementary Material (ESI) for Green 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_IS243
_database_code_depnum_ccdc_archive 'CCDC 2023154'
loop_
_audit_author_name
_audit_author_address
'Kiran Basappa Manjaapa'
;Tunghai University
Taiwan
;
_audit_update_record             
;
2020-08-13 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H16 Br N O3'
_chemical_formula_sum            'C19 H16 Br N O3'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            ?
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         386.24

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'
Br Br -0.2901 2.4595 '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                   15.431(2)
_cell_length_b                   13.4305(19)
_cell_length_c                   7.9796(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.797(6)
_cell_angle_gamma                90
_cell_volume                     1642.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6454
_cell_measurement_theta_min      3.061
_cell_measurement_theta_max      27.933
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.520
_shelx_estimated_absorpt_T_min   0.333
_shelx_estimated_absorpt_T_max   0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3506
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25833
_diffrn_reflns_av_unetI/netI     0.1007
_diffrn_reflns_av_R_equivalents  0.1415
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.985
_diffrn_reflns_theta_max         28.072
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3942
_reflns_number_gt                2356
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0335P)²+13.1117P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3942
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1667
_refine_ls_R_factor_gt           0.0970
_refine_ls_wR_factor_ref         0.2155
_refine_ls_wR_factor_gt          0.1802
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_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
Br Br -0.08463(5) 0.61164(7) 0.35348(12) 0.0508(3) Uani 1 1 d . . . . .
O1 O 0.4175(3) 0.7909(3) 0.1955(5) 0.0258(10) Uani 1 1 d . . . . .
O2 O 0.3414(3) 0.5120(3) 0.0374(6) 0.0321(11) Uani 1 1 d . . . . .
O3 O 0.2947(3) 0.8529(3) 0.0603(6) 0.0312(11) Uani 1 1 d . . . . .
N N 0.6762(4) 0.6778(4) 0.5242(8) 0.0375(15) Uani 1 1 d . . . . .
C1 C 0.4712(4) 0.7119(5) 0.2517(8) 0.0251(14) Uani 1 1 d . . . . .
C2 C 0.5457(4) 0.7350(5) 0.3582(8) 0.0270(14) Uani 1 1 d . . . . .
H2A H 0.558635 0.802254 0.388446 0.032 Uiso 1 1 calc R U . . .
C3 C 0.6022(5) 0.6579(5) 0.4214(8) 0.0287(15) Uani 1 1 d . . . . .
C4 C 0.5799(5) 0.5588(5) 0.3752(8) 0.0287(15) Uani 1 1 d . . . . .
H4A H 0.616375 0.505719 0.419496 0.034 Uiso 1 1 calc R U . . .
C5 C 0.5063(5) 0.5382(5) 0.2676(8) 0.0281(15) Uani 1 1 d . . . . .
H5A H 0.493402 0.471134 0.235958 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4497(4) 0.6138(5) 0.2032(8) 0.0250(13) Uani 1 1 d . . . . .
C7 C 0.3707(4) 0.6007(5) 0.0946(8) 0.0265(14) Uani 1 1 d . . . . .
C8 C 0.2646(5) 0.5310(5) -0.0850(8) 0.0321(16) Uani 1 1 d . . . . .
H8A H 0.217608 0.482942 -0.069354 0.039 Uiso 1 1 calc R U . . .
H8B H 0.279761 0.524557 -0.201640 0.039 Uiso 1 1 calc R U . . .
C9 C 0.2349(5) 0.6375(5) -0.0526(9) 0.0285(15) Uani 1 1 d . . . . .
H9A H 0.221096 0.674330 -0.161469 0.034 Uiso 1 1 calc R U . . .
C10 C 0.3170(4) 0.6782(5) 0.0459(8) 0.0246(14) Uani 1 1 d . . . . .
C11 C 0.3376(4) 0.7780(5) 0.0939(8) 0.0270(14) Uani 1 1 d . . . . .
C12 C 0.7064(5) 0.7796(5) 0.5558(9) 0.0356(17) Uani 1 1 d . . . . .
H12A H 0.760767 0.778935 0.632999 0.053 Uiso 1 1 calc R U . . .
H12B H 0.716923 0.810751 0.448993 0.053 Uiso 1 1 calc R U . . .
H12C H 0.661957 0.817467 0.606569 0.053 Uiso 1 1 calc R U . . .
C13 C 0.7333(5) 0.5976(5) 0.5955(9) 0.0339(16) Uani 1 1 d . . . . .
H13A H 0.783347 0.626125 0.666352 0.051 Uiso 1 1 calc R U . . .
H13B H 0.700761 0.553849 0.664000 0.051 Uiso 1 1 calc R U . . .
H13C H 0.753971 0.558999 0.503824 0.051 Uiso 1 1 calc R U . . .
C14 C 0.1550(5) 0.6364(4) 0.0470(8) 0.0270(15) Uani 1 1 d . . . . .
C15 C 0.0706(5) 0.6406(5) -0.0343(9) 0.0335(17) Uani 1 1 d . . . . .
H15A H 0.061640 0.649018 -0.153262 0.040 Uiso 1 1 calc R U . . .
C16 C -0.0016(5) 0.6328(6) 0.0552(9) 0.0376(18) Uani 1 1 d . . . . .
H16A H -0.059175 0.635764 -0.001888 0.045 Uiso 1 1 calc R U . . .
C17 C 0.0121(4) 0.6206(5) 0.2266(8) 0.0272(14) Uani 1 1 d . . . . .
C18 C 0.0956(4) 0.6172(5) 0.3127(9) 0.0287(14) Uani 1 1 d . . . . .
H18A H 0.104009 0.610174 0.431977 0.034 Uiso 1 1 calc R U . . .
C19 C 0.1662(4) 0.6242(5) 0.2225(8) 0.0277(14) Uani 1 1 d . . . . .
H19A H 0.223592 0.620738 0.280534 0.033 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
Br C17 1.904(6) . ?
O1 C1 1.387(7) . ?
O1 C11 1.405(8) . ?
O2 C7 1.336(7) . ?
O2 C8 1.466(8) . ?
O3 C11 1.217(8) . ?
N C3 1.351(9) . ?
N C12 1.457(9) . ?
N C13 1.463(9) . ?
C1 C2 1.382(9) . ?
C1 C6 1.401(9) . ?
C2 C3 1.409(9) . ?
C2 H2A 0.9500 . ?
C3 C4 1.414(9) . ?
C4 C5 1.369(10) . ?
C4 H4A 0.9500 . ?
C5 C6 1.397(9) . ?
C5 H5A 0.9500 . ?
C6 C7 1.420(9) . ?
C7 C10 1.358(9) . ?
C8 C9 1.534(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.512(9) . ?
C9 C14 1.543(10) . ?
C9 H9A 1.0000 . ?
C10 C11 1.419(9) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.386(9) . ?
C14 C19 1.400(9) . ?
C15 C16 1.396(10) . ?
C15 H15A 0.9500 . ?
C16 C17 1.369(10) . ?
C16 H16A 0.9500 . ?
C17 C18 1.388(9) . ?
C18 C19 1.378(9) . ?
C18 H18A 0.9500 . ?
C19 H19A 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
C1 O1 C11 122.7(5) . . ?
C7 O2 C8 106.6(5) . . ?
C3 N C12 121.4(6) . . ?
C3 N C13 121.1(6) . . ?
C12 N C13 117.2(6) . . ?
C2 C1 O1 116.6(6) . . ?
C2 C1 C6 122.2(6) . . ?
O1 C1 C6 121.2(6) . . ?
C1 C2 C3 119.4(6) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
N C3 C2 121.0(6) . . ?
N C3 C4 120.5(6) . . ?
C2 C3 C4 118.5(6) . . ?
C5 C4 C3 120.8(6) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 121.4(6) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C5 C6 C1 117.7(6) . . ?
C5 C6 C7 126.0(6) . . ?
C1 C6 C7 116.3(6) . . ?
O2 C7 C10 114.6(6) . . ?
O2 C7 C6 123.4(6) . . ?
C10 C7 C6 122.0(6) . . ?
O2 C8 C9 106.6(5) . . ?
O2 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
O2 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
C8 C9 C10 100.1(5) . . ?
C8 C9 C14 110.5(5) . . ?
C10 C9 C14 114.0(6) . . ?
C8 C9 H9A 110.6 . . ?
C10 C9 H9A 110.6 . . ?
C14 C9 H9A 110.6 . . ?
C7 C10 C11 122.5(6) . . ?
C7 C10 C9 108.5(5) . . ?
C11 C10 C9 128.9(6) . . ?
O3 C11 O1 116.2(6) . . ?
O3 C11 C10 128.5(6) . . ?
O1 C11 C10 115.2(6) . . ?
N C12 H12A 109.5 . . ?
N C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N C13 H13A 109.5 . . ?
N C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 118.1(7) . . ?
C15 C14 C9 121.5(6) . . ?
C19 C14 C9 120.3(6) . . ?
C14 C15 C16 121.4(6) . . ?
C14 C15 H15A 119.3 . . ?
C16 C15 H15A 119.3 . . ?
C17 C16 C15 118.8(6) . . ?
C17 C16 H16A 120.6 . . ?
C15 C16 H16A 120.6 . . ?
C16 C17 C18 121.5(6) . . ?
C16 C17 Br 120.1(5) . . ?
C18 C17 Br 118.4(5) . . ?
C19 C18 C17 119.0(6) . . ?
C19 C18 H18A 120.5 . . ?
C17 C18 H18A 120.5 . . ?
C18 C19 C14 121.2(6) . . ?
C18 C19 H19A 119.4 . . ?
C14 C19 H19A 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 O1 C1 C2 -176.6(5) . . . . ?
C11 O1 C1 C6 2.8(9) . . . . ?
O1 C1 C2 C3 179.2(6) . . . . ?
C6 C1 C2 C3 -0.3(10) . . . . ?
C12 N C3 C2 -8.3(10) . . . . ?
C13 N C3 C2 177.5(6) . . . . ?
C12 N C3 C4 171.9(7) . . . . ?
C13 N C3 C4 -2.3(10) . . . . ?
C1 C2 C3 N 179.2(6) . . . . ?
C1 C2 C3 C4 -0.9(10) . . . . ?
N C3 C4 C5 -178.2(6) . . . . ?
C2 C3 C4 C5 1.9(10) . . . . ?
C3 C4 C5 C6 -1.7(10) . . . . ?
C4 C5 C6 C1 0.5(10) . . . . ?
C4 C5 C6 C7 -178.3(6) . . . . ?
C2 C1 C6 C5 0.5(9) . . . . ?
O1 C1 C6 C5 -178.9(6) . . . . ?
C2 C1 C6 C7 179.4(6) . . . . ?
O1 C1 C6 C7 0.0(9) . . . . ?
C8 O2 C7 C10 9.0(7) . . . . ?
C8 O2 C7 C6 -173.5(6) . . . . ?
C5 C6 C7 O2 -1.3(10) . . . . ?
C1 C6 C7 O2 180.0(6) . . . . ?
C5 C6 C7 C10 176.1(6) . . . . ?
C1 C6 C7 C10 -2.7(9) . . . . ?
C7 O2 C8 C9 -17.6(7) . . . . ?
O2 C8 C9 C10 18.5(6) . . . . ?
O2 C8 C9 C14 -102.0(6) . . . . ?
O2 C7 C10 C11 -179.7(6) . . . . ?
C6 C7 C10 C11 2.7(10) . . . . ?
O2 C7 C10 C9 3.7(8) . . . . ?
C6 C7 C10 C9 -173.9(6) . . . . ?
C8 C9 C10 C7 -13.7(7) . . . . ?
C14 C9 C10 C7 104.2(6) . . . . ?
C8 C9 C10 C11 169.9(6) . . . . ?
C14 C9 C10 C11 -72.1(8) . . . . ?
C1 O1 C11 O3 176.4(6) . . . . ?
C1 O1 C11 C10 -2.7(8) . . . . ?
C7 C10 C11 O3 -179.0(7) . . . . ?
C9 C10 C11 O3 -3.1(12) . . . . ?
C7 C10 C11 O1 0.0(9) . . . . ?
C9 C10 C11 O1 175.9(6) . . . . ?
C8 C9 C14 C15 -94.3(7) . . . . ?
C10 C9 C14 C15 153.9(6) . . . . ?
C8 C9 C14 C19 81.4(7) . . . . ?
C10 C9 C14 C19 -30.4(8) . . . . ?
C19 C14 C15 C16 -0.2(10) . . . . ?
C9 C14 C15 C16 175.6(6) . . . . ?
C14 C15 C16 C17 0.0(11) . . . . ?
C15 C16 C17 C18 0.8(11) . . . . ?
C15 C16 C17 Br 179.1(5) . . . . ?
C16 C17 C18 C19 -1.3(10) . . . . ?
Br C17 C18 C19 -179.6(5) . . . . ?
C17 C18 C19 C14 1.1(10) . . . . ?
C15 C14 C19 C18 -0.4(9) . . . . ?
C9 C14 C19 C18 -176.2(6) . . . . ?

_refine_diff_density_max         1.090
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.119

_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_is204a
_database_code_depnum_ccdc_archive 'CCDC 2023155'
loop_
_audit_author_name
_audit_author_address
'Kiran Basappa Manjaapa'
;Tunghai University
Taiwan
;
_audit_update_record             
;
2020-08-13 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H10 N2 O3'
_chemical_formula_sum            'C12 H10 N2 O3'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            ?
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         230.22

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   7.7193(5)
_cell_length_b                   22.2405(17)
_cell_length_c                   5.8028(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     996.23(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.792
_cell_measurement_theta_max      27.923
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8268
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14325
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.213
_diffrn_reflns_theta_max         27.962
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2328
_reflns_number_gt                2274
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_max     0.939
_reflns_Friedel_fraction_full    0.985

_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0725P)²+0.1177P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 976 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.18(19)
_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2328
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0906
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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 0.72006(15) 0.19641(5) 0.7211(2) 0.0200(3) Uani 1 1 d . . . . .
O2 O 0.47983(15) 0.12505(5) 0.1632(2) 0.0218(3) Uani 1 1 d . . . . .
O3 O 0.78364(17) 0.10375(5) 0.8377(2) 0.0259(3) Uani 1 1 d . . . . .
N1 N 0.6489(2) 0.40178(6) 0.5094(3) 0.0221(3) Uani 1 1 d . . . . .
N2 N 0.58997(18) 0.05707(6) 0.4120(3) 0.0228(3) Uani 1 1 d . . . . .
C1 C 0.65385(19) 0.23721(7) 0.5638(3) 0.0166(3) Uani 1 1 d . . . . .
C2 C 0.6769(2) 0.29733(7) 0.6187(3) 0.0177(3) Uani 1 1 d . . . . .
H2B H 0.732591 0.308352 0.758426 0.021 Uiso 1 1 calc R U . . .
C3 C 0.6173(2) 0.34193(7) 0.4661(3) 0.0177(3) Uani 1 1 d . . . . .
C4 C 0.5279(2) 0.32370(7) 0.2631(3) 0.0199(3) Uani 1 1 d . . . . .
H4A H 0.483397 0.353257 0.160786 0.024 Uiso 1 1 calc R U . . .
C5 C 0.5053(2) 0.26382(7) 0.2139(3) 0.0191(3) Uani 1 1 d . . . . .
H5A H 0.445532 0.252506 0.077530 0.023 Uiso 1 1 calc R U . . .
C6 C 0.56892(18) 0.21910(7) 0.3618(3) 0.0164(3) Uani 1 1 d . . . . .
C7 C 0.55756(18) 0.15600(7) 0.3370(3) 0.0179(3) Uani 1 1 d . . . . .
C8 C 0.5059(2) 0.06583(7) 0.2233(3) 0.0243(4) Uani 1 1 d . . . . .
H8A H 0.464618 0.033516 0.131422 0.029 Uiso 1 1 calc R U . . .
C9 C 0.6246(2) 0.11560(7) 0.4886(3) 0.0187(3) Uani 1 1 d . . . . .
C10 C 0.71502(19) 0.13439(7) 0.6923(3) 0.0192(3) Uani 1 1 d . . . . .
C11 C 0.7161(2) 0.41933(8) 0.7327(3) 0.0256(4) Uani 1 1 d . . . . .
H11A H 0.731684 0.463044 0.736896 0.038 Uiso 1 1 calc R U . . .
H11B H 0.634290 0.407238 0.853184 0.038 Uiso 1 1 calc R U . . .
H11C H 0.827870 0.399562 0.758955 0.038 Uiso 1 1 calc R U . . .
C12 C 0.5645(3) 0.44879(7) 0.3772(3) 0.0273(4) Uani 1 1 d . . . . .
H12A H 0.603169 0.488174 0.432848 0.041 Uiso 1 1 calc R U . . .
H12B H 0.594757 0.444477 0.214025 0.041 Uiso 1 1 calc R U . . .
H12C H 0.438699 0.445463 0.395535 0.041 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 C10 1.3901(18) . ?
O1 C1 1.3849(19) . ?
O2 C7 1.360(2) . ?
O2 C8 1.377(2) . ?
O3 C10 1.207(2) . ?
N1 C3 1.376(2) . ?
N1 C12 1.451(2) . ?
N1 C11 1.449(2) . ?
N2 C8 1.288(3) . ?
N2 C9 1.401(2) . ?
C1 C2 1.386(2) . ?
C1 C6 1.402(2) . ?
C2 C3 1.407(2) . ?
C2 H2B 0.9500 . ?
C3 C4 1.424(2) . ?
C4 C5 1.373(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.402(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4134(19) . ?
C7 C9 1.360(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.435(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C10 O1 C1 124.10(13) . . ?
C7 O2 C8 103.39(14) . . ?
C3 N1 C12 121.37(15) . . ?
C3 N1 C11 119.16(15) . . ?
C12 N1 C11 116.05(15) . . ?
C8 N2 C9 103.03(14) . . ?
C2 C1 O1 115.66(15) . . ?
C2 C1 C6 121.97(15) . . ?
O1 C1 C6 122.37(14) . . ?
C1 C2 C3 119.56(16) . . ?
C1 C2 H2B 120.2 . . ?
C3 C2 H2B 120.2 . . ?
N1 C3 C2 120.58(15) . . ?
N1 C3 C4 120.82(15) . . ?
C2 C3 C4 118.58(15) . . ?
C5 C4 C3 120.64(15) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 121.08(16) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C1 C6 C5 118.13(14) . . ?
C1 C6 C7 113.54(14) . . ?
C5 C6 C7 128.33(15) . . ?
O2 C7 C9 108.25(14) . . ?
O2 C7 C6 127.24(15) . . ?
C9 C7 C6 124.51(16) . . ?
N2 C8 O2 115.70(15) . . ?
N2 C8 H8A 122.1 . . ?
O2 C8 H8A 122.1 . . ?
C7 C9 N2 109.63(15) . . ?
C7 C9 C10 121.72(15) . . ?
N2 C9 C10 128.65(15) . . ?
O3 C10 O1 117.64(15) . . ?
O3 C10 C9 128.68(15) . . ?
O1 C10 C9 113.68(14) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 O1 C1 C2 -177.64(14) . . . . ?
C10 O1 C1 C6 2.3(2) . . . . ?
O1 C1 C2 C3 178.53(13) . . . . ?
C6 C1 C2 C3 -1.5(2) . . . . ?
C12 N1 C3 C2 -169.39(16) . . . . ?
C11 N1 C3 C2 -11.1(2) . . . . ?
C12 N1 C3 C4 12.3(2) . . . . ?
C11 N1 C3 C4 170.63(15) . . . . ?
C1 C2 C3 N1 -175.65(14) . . . . ?
C1 C2 C3 C4 2.7(2) . . . . ?
N1 C3 C4 C5 176.25(15) . . . . ?
C2 C3 C4 C5 -2.1(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
O1 C1 C6 C5 179.56(14) . . . . ?
C2 C1 C6 C7 -179.71(14) . . . . ?
O1 C1 C6 C7 0.30(19) . . . . ?
C4 C5 C6 C1 1.1(2) . . . . ?
C4 C5 C6 C7 -179.77(15) . . . . ?
C8 O2 C7 C9 -0.01(16) . . . . ?
C8 O2 C7 C6 -179.87(15) . . . . ?
C1 C6 C7 O2 178.43(14) . . . . ?
C5 C6 C7 O2 -0.7(3) . . . . ?
C1 C6 C7 C9 -1.4(2) . . . . ?
C5 C6 C7 C9 179.42(16) . . . . ?
C9 N2 C8 O2 0.05(18) . . . . ?
C7 O2 C8 N2 -0.03(18) . . . . ?
O2 C7 C9 N2 0.04(18) . . . . ?
C6 C7 C9 N2 179.91(13) . . . . ?
O2 C7 C9 C10 -179.85(13) . . . . ?
C6 C7 C9 C10 0.0(2) . . . . ?
C8 N2 C9 C7 -0.05(17) . . . . ?
C8 N2 C9 C10 179.83(16) . . . . ?
C1 O1 C10 O3 177.02(14) . . . . ?
C1 O1 C10 C9 -3.6(2) . . . . ?
C7 C9 C10 O3 -178.27(17) . . . . ?
N2 C9 C10 O3 1.9(3) . . . . ?
C7 C9 C10 O1 2.4(2) . . . . ?
N2 C9 C10 O1 -177.47(14) . . . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_bmk4739
_database_code_depnum_ccdc_archive 'CCDC 2023156'
loop_
_audit_author_name
_audit_author_address
'Kiran Basappa Manjaapa'
;Tunghai University
Taiwan
;
_audit_update_record             
;
2020-08-13 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H20 N4'
_chemical_formula_sum            'C18 H20 N4'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            red
_diffrn_ambient_temperature      280(2)
_chemical_formula_weight         292.38

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6739(15)
_cell_length_b                   9.7128(14)
_cell_length_c                   9.8240(13)
_cell_angle_alpha                105.074(5)
_cell_angle_beta                 113.757(4)
_cell_angle_gamma                94.114(5)
_cell_volume                     799.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    280(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      2.889
_cell_measurement_theta_max      26.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.380
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8604
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19624
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.889
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.941
_reflns_number_total             2659
_reflns_number_gt                1938
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1306P)²+1.3283P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.023(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2659
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0774
_refine_ls_wR_factor_ref         0.2633
_refine_ls_wR_factor_gt          0.2251
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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
N1 N -0.2717(4) 0.6976(4) 0.0711(4) 0.0587(9) Uani 1 1 d . . . . .
N2 N 0.4556(3) 0.7129(3) 0.4157(3) 0.0487(7) Uani 1 1 d . . . . .
N3 N 1.0883(3) 0.7722(3) 0.7953(4) 0.0573(8) Uani 1 1 d . . . . .
N4 N 0.4516(5) 0.9039(6) 0.7632(5) 0.0991(16) Uani 1 1 d . . . . .
C1 C -0.1173(4) 0.7194(3) 0.1668(4) 0.0424(8) Uani 1 1 d . . . . .
C2 C -0.0597(4) 0.7726(4) 0.3314(4) 0.0490(8) Uani 1 1 d . . . . .
H2B H -0.1269 0.7954 0.3761 0.059 Uiso 1 1 calc R U . . .
C3 C 0.0947(4) 0.7910(4) 0.4262(4) 0.0482(8) Uani 1 1 d . . . . .
H3A H 0.1299 0.8271 0.5343 0.058 Uiso 1 1 calc R U . . .
C4 C 0.2003(4) 0.7572(3) 0.3657(4) 0.0410(8) Uani 1 1 d . . . . .
C5 C 0.1438(4) 0.7072(4) 0.2027(4) 0.0472(8) Uani 1 1 d . . . . .
H5A H 0.2116 0.6850 0.1587 0.057 Uiso 1 1 calc R U . . .
C6 C -0.0102(4) 0.6900(4) 0.1061(4) 0.0505(9) Uani 1 1 d . . . . .
H6A H -0.0440 0.6582 -0.0019 0.061 Uiso 1 1 calc R U . . .
C7 C 0.3629(4) 0.7707(3) 0.4662(4) 0.0437(8) Uani 1 1 d . . . . .
C8 C 0.6153(4) 0.7322(4) 0.5156(4) 0.0423(8) Uani 1 1 d . . . . .
C9 C 0.7090(4) 0.8666(4) 0.6123(4) 0.0493(9) Uani 1 1 d . . . . .
H9A H 0.6662 0.9494 0.6158 0.059 Uiso 1 1 calc R U . . .
C10 C 0.8637(4) 0.8803(4) 0.7034(4) 0.0491(9) Uani 1 1 d . . . . .
H10A H 0.9236 0.9723 0.7657 0.059 Uiso 1 1 calc R U . . .
C11 C 0.9335(4) 0.7584(3) 0.7043(4) 0.0406(8) Uani 1 1 d . . . . .
C12 C 0.8377(4) 0.6231(4) 0.6042(4) 0.0480(8) Uani 1 1 d . . . . .
H12A H 0.8792 0.5395 0.6010 0.058 Uiso 1 1 calc R U . . .
C13 C 0.6844(4) 0.6114(4) 0.5111(4) 0.0467(8) Uani 1 1 d . . . . .
H13A H 0.6251 0.5206 0.4433 0.056 Uiso 1 1 calc R U . . .
C14 C -0.3295(5) 0.6491(5) -0.0970(4) 0.0700(12) Uani 1 1 d . . . . .
H14A H -0.4394 0.6398 -0.1446 0.105 Uiso 1 1 calc R U . . .
H14B H -0.2837 0.7186 -0.1283 0.105 Uiso 1 1 calc R U . . .
H14C H -0.3039 0.5564 -0.1302 0.105 Uiso 1 1 calc R U . . .
C15 C -0.3831(5) 0.7260(7) 0.1333(6) 0.0874(16) Uani 1 1 d . . . . .
H15A H -0.4844 0.7042 0.0483 0.131 Uiso 1 1 calc R U . . .
H15B H -0.3800 0.6660 0.1978 0.131 Uiso 1 1 calc R U . . .
H15C H -0.3588 0.8266 0.1950 0.131 Uiso 1 1 calc R U . . .
C16 C 1.1810(5) 0.9087(5) 0.9105(5) 0.0699(12) Uani 1 1 d . . . . .
H16A H 1.2854 0.8976 0.9622 0.105 Uiso 1 1 calc R U . . .
H16B H 1.1782 0.9813 0.8597 0.105 Uiso 1 1 calc R U . . .
H16C H 1.1411 0.9383 0.9863 0.105 Uiso 1 1 calc R U . . .
C17 C 1.1592(5) 0.6475(5) 0.7905(5) 0.0701(12) Uani 1 1 d . . . . .
H17A H 1.2670 0.6773 0.8611 0.105 Uiso 1 1 calc R U . . .
H17B H 1.1113 0.5791 0.8215 0.105 Uiso 1 1 calc R U . . .
H17C H 1.1468 0.6025 0.6859 0.105 Uiso 1 1 calc R U . . .
C18 C 0.4150(4) 0.8480(5) 0.6334(5) 0.0598(10) 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
N1 C1 1.370(4) . ?
N1 C14 1.440(5) . ?
N1 C15 1.449(5) . ?
N2 C7 1.285(4) . ?
N2 C8 1.423(4) . ?
N3 C11 1.375(4) . ?
N3 C16 1.441(5) . ?
N3 C17 1.434(5) . ?
N4 C18 1.138(5) . ?
C1 C6 1.400(5) . ?
C1 C2 1.411(5) . ?
C2 C3 1.372(5) . ?
C2 H2B 0.9300 . ?
C3 C4 1.393(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.397(5) . ?
C4 C7 1.455(5) . ?
C5 C6 1.375(5) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C18 1.467(5) . ?
C8 C13 1.391(5) . ?
C8 C9 1.385(5) . ?
C9 C10 1.375(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.404(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.405(5) . ?
C12 C13 1.370(5) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C14 121.0(3) . . ?
C1 N1 C15 121.9(3) . . ?
C14 N1 C15 117.0(3) . . ?
C7 N2 C8 121.9(3) . . ?
C11 N3 C16 121.2(3) . . ?
C11 N3 C17 120.9(3) . . ?
C16 N3 C17 117.5(3) . . ?
N1 C1 C6 121.7(3) . . ?
N1 C1 C2 121.1(3) . . ?
C6 C1 C2 117.1(3) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2B 119.7 . . ?
C1 C2 H2B 119.7 . . ?
C2 C3 C4 122.1(3) . . ?
C2 C3 H3A 118.9 . . ?
C4 C3 H3A 118.9 . . ?
C5 C4 C3 117.3(3) . . ?
C5 C4 C7 120.5(3) . . ?
C3 C4 C7 122.2(3) . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C1 C6 C5 121.5(3) . . ?
C1 C6 H6A 119.2 . . ?
C5 C6 H6A 119.2 . . ?
N2 C7 C4 123.1(3) . . ?
N2 C7 C18 120.9(3) . . ?
C4 C7 C18 115.9(3) . . ?
C13 C8 C9 117.5(3) . . ?
C13 C8 N2 118.9(3) . . ?
C9 C8 N2 123.6(3) . . ?
C10 C9 C8 121.5(3) . . ?
C10 C9 H9A 119.2 . . ?
C8 C9 H9A 119.2 . . ?
C9 C10 C11 121.5(3) . . ?
C9 C10 H10A 119.3 . . ?
C11 C10 H10A 119.3 . . ?
N3 C11 C12 122.1(3) . . ?
N3 C11 C10 121.5(3) . . ?
C12 C11 C10 116.4(3) . . ?
C13 C12 C11 121.5(3) . . ?
C13 C12 H12A 119.3 . . ?
C11 C12 H12A 119.3 . . ?
C12 C13 C8 121.6(3) . . ?
C12 C13 H13A 119.2 . . ?
C8 C13 H13A 119.2 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N4 C18 C7 177.3(5) . . ?

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.051

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_h-m   P-1
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

