# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_1121_jfc_szw96_0m
_database_code_depnum_ccdc_archive 'CCDC 2206166'
loop_
_audit_author_name
_audit_author_address
'Zhen-Wei Sun'
;Wuhan Institute of Technology
China
;
_audit_update_record             
;
2022-09-09 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
_audit_creation_date             2021-11-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 Br N4 O'
_chemical_formula_sum            'C23 H17 Br N4 O'
_chemical_formula_weight         445.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.402(5)
_cell_length_b                   10.072(5)
_cell_length_c                   12.350(7)
_cell_angle_alpha                75.414(10)
_cell_angle_beta                 70.202(10)
_cell_angle_gamma                65.089(10)
_cell_volume                     989.8(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3266
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.07
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.099
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1341
_diffrn_reflns_av_unetI/netI     0.1081
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28123
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.194
_diffrn_reflns_theta_max         25.194
_diffrn_reflns_theta_min         2.634
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1783
_reflns_number_total             3547
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1701
_refine_ls_R_factor_gt           0.0652
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+1.6568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1378
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C4(H4), C9(H9), C6(H6), C21(H21), C2(H2), C23(H23), C3(H3A),
 C13(H13), C22(H22), C1(H1), C11(H11), C10(H10)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.04140(9) 0.77172(8) 0.89825(7) 0.0854(3) Uani 1 1 d . . . . .
O1 O 0.7074(5) 0.4791(4) 0.6369(3) 0.0647(11) Uani 1 1 d . . . . .
N1 N 0.6599(5) 0.5752(5) 0.8000(4) 0.0483(11) Uani 1 1 d . . . . .
N3 N 0.3111(6) 0.5833(5) 0.5863(5) 0.0485(14) Uani 1 1 d . . . . .
N4 N 0.3855(5) 0.7330(4) 0.6544(4) 0.0470(11) Uani 1 1 d . . . . .
N2 N 0.3711(6) 0.4911(5) 0.7641(4) 0.0534(12) Uani 1 1 d . . . . .
C7 C 0.3229(6) 0.4808(5) 0.6834(4) 0.0399(13) Uani 1 1 d . . . . .
C12 C 0.3356(6) 0.7106(5) 0.5793(4) 0.0365(12) Uani 1 1 d . . . . .
C8 C 0.2983(6) 0.8278(5) 0.4820(4) 0.0377(12) Uani 1 1 d . . . . .
C18 C 0.5233(7) 0.6491(6) 0.8846(5) 0.0459(14) Uani 1 1 d . . . . .
C5 C 0.2740(6) 0.3551(6) 0.6936(4) 0.0434(13) Uani 1 1 d . . . . .
C15 C 0.4272(7) 0.6110(5) 0.7460(4) 0.0468(14) Uani 1 1 d . . . . .
C19 C 0.3830(7) 0.6721(5) 0.8578(4) 0.0449(14) Uani 1 1 d . . . . .
C16 C 0.6164(8) 0.5452(6) 0.7176(5) 0.0500(15) Uani 1 1 d . . . . .
C20 C 0.2351(7) 0.7419(6) 0.9308(5) 0.0511(15) Uani 1 1 d . . . . .
C14 C 0.3725(7) 0.9293(6) 0.4480(5) 0.0513(15) Uani 1 1 d . . . . .
H14 H 0.445838 0.921856 0.486264 0.062 Uiso 1 1 calc R . . . .
C4 C 0.2072(7) 0.3424(6) 0.6153(5) 0.0543(15) Uani 1 1 d . . . . .
H4 H 0.186550 0.416740 0.553907 0.065 Uiso 1 1 calc R . . . .
C9 C 0.1897(7) 0.8407(6) 0.4249(5) 0.0617(17) Uani 1 1 d . . . . .
H9 H 0.137314 0.773990 0.446777 0.074 Uiso 1 1 calc R . . . .
C6 C 0.3010(8) 0.2444(6) 0.7845(5) 0.0659(17) Uani 1 1 d . . . . .
H6 H 0.345688 0.251895 0.838346 0.079 Uiso 1 1 calc R . . . .
C21 C 0.2284(8) 0.7887(6) 1.0295(5) 0.0650(17) Uani 1 1 d . . . . .
H21 H 0.128744 0.836727 1.078987 0.078 Uiso 1 1 calc R . . . .
C2 C 0.1992(8) 0.1102(7) 0.7185(6) 0.0707(19) Uani 1 1 d . . . . .
H2 H 0.174926 0.027125 0.726542 0.085 Uiso 1 1 calc R . . . .
C23 C 0.5204(8) 0.6934(6) 0.9815(5) 0.0624(17) Uani 1 1 d . . . . .
H23 H 0.616082 0.676946 0.998339 0.075 Uiso 1 1 calc R . . . .
C17 C 0.8275(7) 0.5304(6) 0.8014(5) 0.0679(17) Uani 1 1 d . . . . .
H17A H 0.865980 0.609002 0.762232 0.102 Uiso 1 1 calc GR . . . .
H17B H 0.893292 0.444240 0.762607 0.102 Uiso 1 1 calc GR . . . .
H17C H 0.834093 0.508301 0.880220 0.102 Uiso 1 1 calc GR . . . .
C3 C 0.1705(7) 0.2185(7) 0.6280(6) 0.0676(18) Uani 1 1 d . . . . .
H3A H 0.126286 0.209437 0.574606 0.081 Uiso 1 1 calc R . . . .
C13 C 0.3408(8) 1.0416(6) 0.3587(5) 0.0675(18) Uani 1 1 d . . . . .
H13 H 0.392371 1.108979 0.336403 0.081 Uiso 1 1 calc R . . . .
C22 C 0.3712(10) 0.7628(7) 1.0530(5) 0.0699(18) Uani 1 1 d . . . . .
H22 H 0.366631 0.793399 1.119593 0.084 Uiso 1 1 calc R . . . .
C1 C 0.2630(9) 0.1232(7) 0.7969(6) 0.078(2) Uani 1 1 d . . . . .
H1 H 0.281013 0.049699 0.859260 0.094 Uiso 1 1 calc R . . . .
C11 C 0.2319(9) 1.0522(7) 0.3032(5) 0.077(2) Uani 1 1 d . . . . .
H11 H 0.208140 1.128129 0.243332 0.092 Uiso 1 1 calc R . . . .
C10 C 0.1586(9) 0.9527(7) 0.3352(6) 0.082(2) Uani 1 1 d . . . . .
H10 H 0.086188 0.960086 0.296046 0.098 Uiso 1 1 calc R . . . .
H3 H 0.287(6) 0.575(5) 0.544(4) 0.023(17) 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
Br1 C20 1.882(5) . ?
O1 C16 1.202(6) . ?
N1 C18 1.404(7) . ?
N1 C16 1.355(6) . ?
N1 C17 1.450(7) . ?
N3 C7 1.373(7) . ?
N3 C12 1.373(7) . ?
N4 C12 1.273(6) . ?
N4 C15 1.462(6) . ?
N2 C7 1.267(6) . ?
N2 C15 1.452(6) . ?
C7 C5 1.483(7) . ?
C12 C8 1.477(6) . ?
C8 C14 1.376(7) . ?
C8 C9 1.373(7) . ?
C18 C19 1.380(7) . ?
C18 C23 1.367(7) . ?
C5 C4 1.373(7) . ?
C5 C6 1.376(7) . ?
C15 C19 1.510(7) . ?
C15 C16 1.558(8) . ?
C19 C20 1.374(7) . ?
C20 C21 1.387(8) . ?
C14 C13 1.376(7) . ?
C4 C3 1.389(8) . ?
C9 C10 1.378(7) . ?
C6 C1 1.370(8) . ?
C21 C22 1.374(8) . ?
C2 C3 1.361(8) . ?
C2 C1 1.356(8) . ?
C23 C22 1.372(8) . ?
C13 C11 1.369(8) . ?
C11 C10 1.354(8) . ?

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
C18 N1 C17 125.1(5) . . ?
C16 N1 C18 111.6(5) . . ?
C16 N1 C17 123.3(5) . . ?
C12 N3 C7 120.0(5) . . ?
C12 N4 C15 116.5(4) . . ?
C7 N2 C15 117.0(4) . . ?
N3 C7 C5 117.8(5) . . ?
N2 C7 N3 122.7(5) . . ?
N2 C7 C5 119.5(5) . . ?
N3 C12 C8 118.4(5) . . ?
N4 C12 N3 122.8(5) . . ?
N4 C12 C8 118.8(5) . . ?
C14 C8 C12 119.3(5) . . ?
C9 C8 C12 122.3(5) . . ?
C9 C8 C14 118.4(5) . . ?
C19 C18 N1 109.9(5) . . ?
C23 C18 N1 127.9(5) . . ?
C23 C18 C19 122.3(6) . . ?
C4 C5 C7 123.3(5) . . ?
C4 C5 C6 118.7(5) . . ?
C6 C5 C7 118.0(5) . . ?
N4 C15 C19 109.4(4) . . ?
N4 C15 C16 106.3(4) . . ?
N2 C15 N4 118.7(4) . . ?
N2 C15 C19 111.5(4) . . ?
N2 C15 C16 108.2(4) . . ?
C19 C15 C16 101.2(4) . . ?
C18 C19 C15 109.3(5) . . ?
C20 C19 C18 119.0(5) . . ?
C20 C19 C15 131.6(5) . . ?
O1 C16 N1 126.1(6) . . ?
O1 C16 C15 125.9(5) . . ?
N1 C16 C15 108.0(5) . . ?
C19 C20 Br1 120.1(4) . . ?
C19 C20 C21 120.0(5) . . ?
C21 C20 Br1 119.9(5) . . ?
C13 C14 C8 121.7(5) . . ?
C5 C4 C3 119.9(6) . . ?
C8 C9 C10 119.9(5) . . ?
C1 C6 C5 120.9(6) . . ?
C22 C21 C20 119.0(6) . . ?
C1 C2 C3 120.1(6) . . ?
C18 C23 C22 117.6(6) . . ?
C2 C3 C4 120.2(6) . . ?
C11 C13 C14 118.8(6) . . ?
C23 C22 C21 122.1(6) . . ?
C2 C1 C6 120.2(6) . . ?
C10 C11 C13 120.3(6) . . ?
C11 C10 C9 120.9(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_a
_database_code_depnum_ccdc_archive 'CCDC 2206220'
loop_
_audit_author_name
_audit_author_address
'Zhen-Wei Sun'
;Wuhan Institute of Technology
China
;
_audit_update_record             
;
2022-09-09 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 N4 O2'
_chemical_formula_weight         306.32

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      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                   6.992
_cell_length_b                   9.641
_cell_length_c                   12.262
_cell_angle_alpha                68.00
_cell_angle_beta                 84.19
_cell_angle_gamma                74.40
_cell_volume                     738.2
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1179
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      19.64

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2599
_diffrn_reflns_av_unetI/netI     0.1608
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.386
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2599
_reflns_number_gt                1184
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1261P)²] 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         2599
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2595
_refine_ls_R_factor_gt           0.1212
_refine_ls_wR_factor_ref         0.2923
_refine_ls_wR_factor_gt          0.2298
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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
C1 C 0.8761(9) 0.3588(7) 0.3166(5) 0.0580(17) Uani 1 1 d . . . . .
H1 H 0.8993 0.2534 0.3598 0.070 Uiso 1 1 calc R U . . .
C2 C 0.8992(10) 0.4089(9) 0.1965(6) 0.073(2) Uani 1 1 d . . . . .
H2 H 0.9374 0.3370 0.1598 0.087 Uiso 1 1 calc R U . . .
C3 C 0.8671(10) 0.5621(9) 0.1307(6) 0.072(2) Uani 1 1 d . . . . .
H3 H 0.8809 0.5951 0.0493 0.087 Uiso 1 1 calc R U . . .
C4 C 0.8140(10) 0.6670(8) 0.1856(5) 0.0690(19) Uani 1 1 d . . . . .
H4 H 0.7944 0.7718 0.1411 0.083 Uiso 1 1 calc R U . . .
C5 C 0.7890(9) 0.6196(8) 0.3070(5) 0.0592(17) Uani 1 1 d . . . . .
H5 H 0.7525 0.6922 0.3430 0.071 Uiso 1 1 calc R U . . .
C6 C 0.8190(8) 0.4624(7) 0.3744(5) 0.0454(15) Uani 1 1 d . . . . .
C7 C 0.7891(8) 0.4138(7) 0.5038(5) 0.0457(15) Uani 1 1 d . . . . .
C8 C 0.7916(9) 0.2151(7) 0.6825(5) 0.0534(16) Uani 1 1 d . . . . .
C9 C 0.8207(11) 0.0573(7) 0.7534(6) 0.081(2) Uani 1 1 d . . . . .
H9 H 0.8642 -0.0188 0.7209 0.097 Uiso 1 1 calc R U . . .
C10 C 0.7828(12) 0.0193(7) 0.8722(6) 0.087(2) Uani 1 1 d . . . . .
H10 H 0.8019 -0.0846 0.9192 0.105 Uiso 1 1 calc R U . . .
C11 C 0.7175(11) 0.1285(7) 0.9252(6) 0.076(2) Uani 1 1 d . . . . .
H11 H 0.6938 0.0975 1.0057 0.091 Uiso 1 1 calc R U . . .
C12 C 0.6883(8) 0.2832(7) 0.8571(5) 0.0528(16) Uani 1 1 d . . . . .
C13 C 0.7266(8) 0.3242(6) 0.7360(5) 0.0486(15) Uani 1 1 d . . . . .
C14 C 0.6973(7) 0.4797(6) 0.6632(5) 0.0397(14) Uani 1 1 d . . . . .
C15 C 0.5994(9) 0.5546(7) 0.8324(5) 0.0532(16) Uani 1 1 d . . . . .
C16 C 0.7022(11) 0.9550(8) 0.4786(6) 0.073(2) Uani 1 1 d . . . . .
H16A H 0.8165 0.8774 0.4686 0.088 Uiso 1 1 calc R U . . .
H16B H 0.7451 1.0475 0.4662 0.088 Uiso 1 1 calc R U . . .
C17 C 0.4521(11) 1.0096(7) 0.6095(6) 0.073(2) Uani 1 1 d . . . . .
H17A H 0.4866 1.1040 0.6011 0.088 Uiso 1 1 calc R U . . .
H17B H 0.3990 0.9690 0.6880 0.088 Uiso 1 1 calc R U . . .
N1 N 0.8218(6) 0.2624(5) 0.5615(4) 0.0496(13) Uani 1 1 d . . . . .
N2 N 0.7272(6) 0.5285(5) 0.5489(4) 0.0463(13) Uani 1 1 d . . . . .
N3 N 0.6391(7) 0.5866(5) 0.7151(4) 0.0511(13) Uani 1 1 d . . . . .
H3A H 0.6262 0.6819 0.6707 0.061 Uiso 1 1 calc R U . . .
N4 N 0.6256(7) 0.4023(6) 0.8994(4) 0.0572(14) Uani 1 1 d . . . . .
H4A H 0.6013 0.3783 0.9734 0.069 Uiso 1 1 calc R U . . .
O1 O 0.5385(7) 0.6558(5) 0.8733(3) 0.0690(14) Uani 1 1 d . . . . .
O2 O 0.6261(6) 0.8998(4) 0.5953(4) 0.0662(13) 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
C1 C2 1.374(8) . ?
C1 C6 1.385(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.360(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.486(7) . ?
C7 N1 1.328(7) . ?
C7 N2 1.367(6) . ?
C8 N1 1.391(7) . ?
C8 C13 1.393(7) . ?
C8 C9 1.410(7) . ?
C9 C10 1.379(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.390(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(8) . ?
C11 H11 0.9300 . ?
C12 N4 1.381(7) . ?
C12 C13 1.404(7) . ?
C13 C14 1.398(7) . ?
C14 N2 1.315(6) . ?
C14 N3 1.359(6) . ?
C15 O1 1.219(6) . ?
C15 N4 1.359(7) . ?
C15 N3 1.369(7) . ?
C16 O2 1.429(7) . ?
C16 C17 1.486(9) 2_676 ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O2 1.426(7) . ?
C17 C16 1.486(9) 2_676 ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
N3 H3A 0.8600 . ?
N4 H4A 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.2(6) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C3 C2 C1 120.9(7) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 119.2(6) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 121.1(6) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 119.7(6) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 117.8(6) . . ?
C1 C6 C7 123.1(6) . . ?
C5 C6 C7 119.1(6) . . ?
N1 C7 N2 127.8(5) . . ?
N1 C7 C6 115.3(5) . . ?
N2 C7 C6 117.0(5) . . ?
N1 C8 C13 120.2(5) . . ?
N1 C8 C9 121.3(6) . . ?
C13 C8 C9 118.5(5) . . ?
C10 C9 C8 118.1(6) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C9 C10 C11 123.3(6) . . ?
C9 C10 H10 118.4 . . ?
C11 C10 H10 118.4 . . ?
C12 C11 C10 119.3(6) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
N4 C12 C11 124.8(5) . . ?
N4 C12 C13 116.9(5) . . ?
C11 C12 C13 118.2(6) . . ?
C14 C13 C8 117.1(5) . . ?
C14 C13 C12 120.3(5) . . ?
C8 C13 C12 122.6(5) . . ?
N2 C14 N3 118.1(5) . . ?
N2 C14 C13 124.4(5) . . ?
N3 C14 C13 117.5(5) . . ?
O1 C15 N4 122.2(6) . . ?
O1 C15 N3 122.4(6) . . ?
N4 C15 N3 115.3(5) . . ?
O2 C16 C17 110.6(5) . 2_676 ?
O2 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 2_676 . ?
O2 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 2_676 . ?
H16A C16 H16B 108.1 . . ?
O2 C17 C16 111.5(5) . 2_676 ?
O2 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 2_676 . ?
O2 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 2_676 . ?
H17A C17 H17B 108.0 . . ?
C7 N1 C8 116.0(5) . . ?
C14 N2 C7 114.6(5) . . ?
C14 N3 C15 125.2(5) . . ?
C14 N3 H3A 117.4 . . ?
C15 N3 H3A 117.4 . . ?
C15 N4 C12 124.7(5) . . ?
C15 N4 H4A 117.6 . . ?
C12 N4 H4A 117.6 . . ?
C17 O2 C16 110.1(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
C6 C1 C2 C3 0.2(10) . . . . ?
C1 C2 C3 C4 1.0(10) . . . . ?
C2 C3 C4 C5 -1.2(10) . . . . ?
C3 C4 C5 C6 0.2(9) . . . . ?
C2 C1 C6 C5 -1.1(9) . . . . ?
C2 C1 C6 C7 179.0(5) . . . . ?
C4 C5 C6 C1 0.9(8) . . . . ?
C4 C5 C6 C7 -179.2(5) . . . . ?
C1 C6 C7 N1 0.3(8) . . . . ?
C5 C6 C7 N1 -179.6(5) . . . . ?
C1 C6 C7 N2 -178.2(5) . . . . ?
C5 C6 C7 N2 1.9(7) . . . . ?
N1 C8 C9 C10 -178.3(6) . . . . ?
C13 C8 C9 C10 0.1(10) . . . . ?
C8 C9 C10 C11 0.1(12) . . . . ?
C9 C10 C11 C12 0.0(12) . . . . ?
C10 C11 C12 N4 -179.4(6) . . . . ?
C10 C11 C12 C13 -0.1(10) . . . . ?
N1 C8 C13 C14 -1.0(8) . . . . ?
C9 C8 C13 C14 -179.4(5) . . . . ?
N1 C8 C13 C12 178.1(5) . . . . ?
C9 C8 C13 C12 -0.3(9) . . . . ?
N4 C12 C13 C14 -1.3(8) . . . . ?
C11 C12 C13 C14 179.4(6) . . . . ?
N4 C12 C13 C8 179.6(5) . . . . ?
C11 C12 C13 C8 0.3(9) . . . . ?
C8 C13 C14 N2 -0.1(8) . . . . ?
C12 C13 C14 N2 -179.2(5) . . . . ?
C8 C13 C14 N3 -178.2(5) . . . . ?
C12 C13 C14 N3 2.6(8) . . . . ?
N2 C7 N1 C8 -0.8(8) . . . . ?
C6 C7 N1 C8 -179.1(5) . . . . ?
C13 C8 N1 C7 1.4(8) . . . . ?
C9 C8 N1 C7 179.7(6) . . . . ?
N3 C14 N2 C7 178.8(4) . . . . ?
C13 C14 N2 C7 0.6(8) . . . . ?
N1 C7 N2 C14 -0.2(8) . . . . ?
C6 C7 N2 C14 178.1(4) . . . . ?
N2 C14 N3 C15 179.0(5) . . . . ?
C13 C14 N3 C15 -2.7(8) . . . . ?
O1 C15 N3 C14 -176.4(5) . . . . ?
N4 C15 N3 C14 1.3(8) . . . . ?
O1 C15 N4 C12 177.9(5) . . . . ?
N3 C15 N4 C12 0.3(8) . . . . ?
C11 C12 N4 C15 179.1(6) . . . . ?
C13 C12 N4 C15 -0.2(9) . . . . ?
C16 C17 O2 C16 56.8(7) 2_676 . . . ?
C17 C16 O2 C17 -56.3(7) 2_676 . . . ?

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.055


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
