# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc2gq3q1
_database_code_depnum_ccdc_archive 'CCDC 2285373'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D3CC04144A 2023
loop_
_audit_author_name
_audit_author_address
'P. Anbarasan'
;Indian Institute of Technology Madras
India
;
_audit_update_record             
;
2023-07-29 deposited with the CCDC.	2024-05-01 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            'C16 H13 N O'
_chemical_formula_weight         235.27

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                   7.4062(4)
_cell_length_b                   7.8098(5)
_cell_length_c                   10.9025(6)
_cell_angle_alpha                101.137(2)
_cell_angle_beta                 93.235(2)
_cell_angle_gamma                96.394(2)
_cell_volume                     612.92(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9884
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      33.05

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.006
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   1.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.604
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS, Bruker 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  
'Bruker axs kappa apex3 PHOTON II Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39332
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.242
_diffrn_reflns_theta_max         33.143
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4672
_reflns_number_gt                3264
_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       'APEX3(Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_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)+(0.1235P)²+0.0886P] 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         4672
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.2091
_refine_ls_wR_factor_gt          0.1773
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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 0.28208(14) 0.28667(16) 0.58555(11) 0.0358(2) Uani 1 1 d . . . . .
C2 C 0.43381(13) 0.24894(16) 0.51922(12) 0.0360(2) Uani 1 1 d . . . . .
C3 C 0.36456(14) 0.15941(16) 0.39420(12) 0.0363(2) Uani 1 1 d . . . . .
C4 C 0.44327(18) 0.0943(2) 0.28329(14) 0.0467(3) Uani 1 1 d . . . . .
H4 H 0.569301 0.103111 0.281373 0.056 Uiso 1 1 calc R U . . .
C5 C 0.3312(2) 0.0171(2) 0.17716(15) 0.0569(4) Uani 1 1 d . . . . .
H5 H 0.383036 -0.025591 0.103400 0.068 Uiso 1 1 calc R U . . .
C6 C 0.1410(2) 0.0015(2) 0.17800(15) 0.0576(4) Uani 1 1 d . . . . .
H6 H 0.068851 -0.053186 0.105436 0.069 Uiso 1 1 calc R U . . .
C7 C 0.05945(18) 0.0662(2) 0.28510(14) 0.0503(3) Uani 1 1 d . . . . .
H7 H -0.066705 0.056540 0.286294 0.060 Uiso 1 1 calc R U . . .
C8 C 0.17315(15) 0.14635(17) 0.39107(12) 0.0384(3) Uani 1 1 d . . . . .
C9 C 0.26199(14) 0.37489(17) 0.71587(12) 0.0381(3) Uani 1 1 d . . . . .
C10 C 0.1930(2) 0.5346(2) 0.73876(14) 0.0508(3) Uani 1 1 d . . . . .
H10 H 0.160455 0.586491 0.672153 0.061 Uiso 1 1 calc R U . . .
C11 C 0.1722(3) 0.6177(3) 0.86086(16) 0.0652(5) Uani 1 1 d . . . . .
H11 H 0.127831 0.726053 0.875750 0.078 Uiso 1 1 calc R U . . .
C12 C 0.2168(2) 0.5407(3) 0.95993(15) 0.0618(4) Uani 1 1 d . . . . .
H12 H 0.202456 0.596915 1.041483 0.074 Uiso 1 1 calc R U . . .
C13 C 0.2824(3) 0.3811(3) 0.93848(16) 0.0618(4) Uani 1 1 d . . . . .
H13 H 0.311516 0.328506 1.005401 0.074 Uiso 1 1 calc R U . . .
C14 C 0.3053(2) 0.2979(2) 0.81668(15) 0.0533(4) Uani 1 1 d . . . . .
H14 H 0.349965 0.189680 0.802506 0.064 Uiso 1 1 calc R U . . .
C15 C 0.62635(14) 0.29137(18) 0.56180(13) 0.0402(3) Uani 1 1 d . . . . .
C16 C 0.68814(19) 0.4093(3) 0.68595(16) 0.0568(4) Uani 1 1 d . . . . .
H16A H 0.583821 0.444645 0.727951 0.085 Uiso 1 1 calc R U . . .
H16B H 0.756686 0.347198 0.736411 0.085 Uiso 1 1 calc R U . . .
H16C H 0.763506 0.511467 0.673044 0.085 Uiso 1 1 calc R U . . .
N1 N 0.12831(13) 0.22485(16) 0.50772(10) 0.0421(3) Uani 1 1 d . . . . .
H1N H 0.019(3) 0.235(2) 0.5288(17) 0.050 Uiso 1 1 d . U . . .
O1 O 0.74186(12) 0.23210(18) 0.49373(11) 0.0572(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3639(15) . ?
C1 C2 1.3985(14) . ?
C1 C9 1.4779(17) . ?
C2 C3 1.4432(17) . ?
C2 C15 1.4558(15) . ?
C3 C4 1.4030(17) . ?
C3 C8 1.4080(15) . ?
C4 C5 1.379(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.3889(18) . ?
C7 H7 0.9300 . ?
C8 N1 1.3767(16) . ?
C9 C10 1.384(2) . ?
C9 C14 1.390(2) . ?
C10 C11 1.389(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O1 1.2346(15) . ?
C15 C16 1.498(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 H1N 0.860(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 108.63(11) . . ?
N1 C1 C9 118.43(9) . . ?
C2 C1 C9 132.94(10) . . ?
C1 C2 C3 106.59(9) . . ?
C1 C2 C15 128.81(12) . . ?
C3 C2 C15 124.59(10) . . ?
C4 C3 C8 118.07(12) . . ?
C4 C3 C2 135.08(11) . . ?
C8 C3 C2 106.80(10) . . ?
C5 C4 C3 119.10(12) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.46(14) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 120.84(14) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 117.38(13) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 H7 121.3 . . ?
N1 C8 C7 129.25(11) . . ?
N1 C8 C3 107.66(10) . . ?
C7 C8 C3 123.09(12) . . ?
C10 C9 C14 118.83(13) . . ?
C10 C9 C1 119.83(12) . . ?
C14 C9 C1 121.31(12) . . ?
C9 C10 C11 120.21(14) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.38(16) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.03(15) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 119.95(16) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.59(15) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
O1 C15 C2 119.69(13) . . ?
O1 C15 C16 119.00(11) . . ?
C2 C15 C16 121.30(11) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 N1 C8 110.32(9) . . ?
C1 N1 H1N 124.5(12) . . ?
C8 N1 H1N 125.2(12) . . ?

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
N1 C1 C2 C3 0.11(15) . . . . ?
C9 C1 C2 C3 179.87(13) . . . . ?
N1 C1 C2 C15 178.92(13) . . . . ?
C9 C1 C2 C15 -1.3(2) . . . . ?
C1 C2 C3 C4 176.95(15) . . . . ?
C15 C2 C3 C4 -1.9(2) . . . . ?
C1 C2 C3 C8 -0.31(14) . . . . ?
C15 C2 C3 C8 -179.18(12) . . . . ?
C8 C3 C4 C5 -1.5(2) . . . . ?
C2 C3 C4 C5 -178.49(15) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 N1 178.24(15) . . . . ?
C6 C7 C8 C3 -1.8(2) . . . . ?
C4 C3 C8 N1 -177.42(12) . . . . ?
C2 C3 C8 N1 0.40(14) . . . . ?
C4 C3 C8 C7 2.6(2) . . . . ?
C2 C3 C8 C7 -179.59(13) . . . . ?
N1 C1 C9 C10 -66.90(17) . . . . ?
C2 C1 C9 C10 113.36(16) . . . . ?
N1 C1 C9 C14 110.88(15) . . . . ?
C2 C1 C9 C14 -68.9(2) . . . . ?
C14 C9 C10 C11 1.6(2) . . . . ?
C1 C9 C10 C11 179.45(14) . . . . ?
C9 C10 C11 C12 -1.2(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C9 -0.1(3) . . . . ?
C10 C9 C14 C13 -1.0(2) . . . . ?
C1 C9 C14 C13 -178.79(13) . . . . ?
C1 C2 C15 O1 172.82(13) . . . . ?
C3 C2 C15 O1 -8.6(2) . . . . ?
C1 C2 C15 C16 -8.5(2) . . . . ?
C3 C2 C15 C16 170.08(13) . . . . ?
C2 C1 N1 C8 0.14(16) . . . . ?
C9 C1 N1 C8 -179.66(11) . . . . ?
C7 C8 N1 C1 179.65(15) . . . . ?
C3 C8 N1 C1 -0.34(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O1 0.860(19) 2.065(19) 2.8650(13) 154.4(17) 1_455 yes

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.052



####################################################################### 
# 
# 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_shelx_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc2gq3nz
_database_code_depnum_ccdc_archive 'CCDC 2285371'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D3CC04144A 2023
loop_
_audit_author_name
_audit_author_address
'P. Anbarasan'
;Indian Institute of Technology Madras
India
;
_audit_update_record             
;
2023-07-29 deposited with the CCDC.	2024-05-01 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         '	C11 H11 N O'

_chemical_formula_sum            'C11 H11 N O'
_chemical_formula_weight         173.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   13.5293(7)
_cell_length_b                   7.3263(3)
_cell_length_c                   19.0986(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.741(3)
_cell_angle_gamma                90
_cell_volume                     1865.75(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6004
_cell_measurement_theta_min      4.70
_cell_measurement_theta_max      71.47

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.632
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.4109
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   'SADABS(BRUKER 2017)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a

_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_measurement_device_type  
'Bruker axs kappa apex3 PHOTON III Diffractometer'
_diffrn_measurement_method       'ω and φ scan'





_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13865
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         6.640
_diffrn_reflns_theta_max         66.417
_diffrn_reflns_theta_full        66.417
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1632
_reflns_number_gt                1268
_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       'APEX3(Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'



_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)+(0.1026P)²+0.4119P] 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         1632
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1763
_refine_ls_wR_factor_gt          0.1576
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
C1 C 0.64237(15) 0.5067(3) 0.63907(12) 0.0805(6) Uani 1 1 d . . . . .
H1 H 0.647450 0.380151 0.638297 0.097 Uiso 1 1 calc R U . . .
C2 C 0.64612(18) 0.5984(4) 0.70220(14) 0.0951(7) Uani 1 1 d . . . . .
H2 H 0.653595 0.532205 0.744307 0.114 Uiso 1 1 calc R U . . .
C3 C 0.6390(2) 0.7883(4) 0.70488(15) 0.0974(8) Uani 1 1 d . . . . .
H3 H 0.641025 0.846165 0.748434 0.117 Uiso 1 1 calc R U . . .
C4 C 0.62907(15) 0.8904(3) 0.64375(14) 0.0870(7) Uani 1 1 d . . . . .
H4 H 0.625326 1.017092 0.645103 0.104 Uiso 1 1 calc R U . . .
C5 C 0.62483(13) 0.7982(3) 0.58020(12) 0.0722(6) Uani 1 1 d . . . . .
C6 C 0.63078(12) 0.6072(3) 0.57605(11) 0.0691(6) Uani 1 1 d . . . . .
C7 C 0.62496(12) 0.5622(2) 0.50182(11) 0.0663(5) Uani 1 1 d . . . . .
C8 C 0.61544(13) 0.7269(3) 0.46474(12) 0.0688(6) Uani 1 1 d . . . . .
C9 C 0.60297(17) 0.7720(3) 0.38775(13) 0.0854(7) Uani 1 1 d . . . . .
H9A H 0.585035 0.898346 0.380867 0.128 Uiso 1 1 calc R U . . .
H9B H 0.551019 0.697271 0.361821 0.128 Uiso 1 1 calc R U . . .
H9C H 0.664823 0.749651 0.370913 0.128 Uiso 1 1 calc R U . . .
C10 C 0.62736(13) 0.3780(3) 0.47454(12) 0.0693(6) Uani 1 1 d . . . . .
C11 C 0.63397(17) 0.3422(3) 0.39827(13) 0.0846(7) Uani 1 1 d . . . . .
H11A H 0.684463 0.419381 0.384113 0.127 Uiso 1 1 calc R U . . .
H11B H 0.570385 0.367741 0.369201 0.127 Uiso 1 1 calc R U . . .
H11C H 0.651303 0.216679 0.392607 0.127 Uiso 1 1 calc R U . . .
N1 N 0.61545(11) 0.8657(2) 0.51220(10) 0.0747(5) Uani 1 1 d . . . . .
O1 O 0.62519(11) 0.24710(19) 0.51497(8) 0.0830(5) Uani 1 1 d . . . . .
H1A H 0.6133(19) 0.992(4) 0.4975(13) 0.116(9) 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
C1 C2 1.374(3) . ?
C1 C6 1.397(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.396(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.375(3) . ?
C5 C6 1.404(3) . ?
C6 C7 1.445(3) . ?
C7 C8 1.394(3) . ?
C7 C10 1.449(3) . ?
C8 N1 1.362(3) . ?
C8 C9 1.489(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O1 1.235(2) . ?
C10 C11 1.498(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N1 H1A 0.97(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
C2 C1 C6 118.7(2) . . ?
C2 C1 H1 120.6 . . ?
C6 C1 H1 120.6 . . ?
C1 C2 C3 121.8(2) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 117.6(2) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
N1 C5 C4 129.58(19) . . ?
N1 C5 C6 107.56(18) . . ?
C4 C5 C6 122.9(2) . . ?
C1 C6 C5 118.4(2) . . ?
C1 C6 C7 134.79(18) . . ?
C5 C6 C7 106.79(17) . . ?
C8 C7 C6 106.61(16) . . ?
C8 C7 C10 129.0(2) . . ?
C6 C7 C10 124.39(18) . . ?
N1 C8 C7 108.58(19) . . ?
N1 C8 C9 118.58(17) . . ?
C7 C8 C9 132.81(19) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C7 119.6(2) . . ?
O1 C10 C11 118.93(18) . . ?
C7 C10 C11 121.44(18) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 N1 C5 110.47(17) . . ?
C8 N1 H1A 121.7(15) . . ?
C5 N1 H1A 127.7(15) . . ?

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(3) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 N1 -179.8(2) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C2 C1 C6 C7 179.1(2) . . . . ?
N1 C5 C6 C1 178.98(16) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
N1 C5 C6 C7 0.25(19) . . . . ?
C4 C5 C6 C7 -179.30(17) . . . . ?
C1 C6 C7 C8 -178.64(19) . . . . ?
C5 C6 C7 C8 -0.22(19) . . . . ?
C1 C6 C7 C10 2.3(3) . . . . ?
C5 C6 C7 C10 -179.33(16) . . . . ?
C6 C7 C8 N1 0.1(2) . . . . ?
C10 C7 C8 N1 179.16(16) . . . . ?
C6 C7 C8 C9 -177.75(19) . . . . ?
C10 C7 C8 C9 1.3(3) . . . . ?
C8 C7 C10 O1 -172.03(17) . . . . ?
C6 C7 C10 O1 6.9(3) . . . . ?
C8 C7 C10 C11 8.9(3) . . . . ?
C6 C7 C10 C11 -172.22(17) . . . . ?
C7 C8 N1 C5 0.0(2) . . . . ?
C9 C8 N1 C5 178.26(16) . . . . ?
C4 C5 N1 C8 179.33(19) . . . . ?
C6 C5 N1 C8 -0.19(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O1 0.97(3) 1.90(3) 2.798(2) 153(2) 1_565 yes

_refine_diff_density_max         0.123
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.035



####################################################################### 
# 
# 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_958
_audit_block_doi                 10.5517/ccdc.csd.cc2gq3p0
_database_code_depnum_ccdc_archive 'CCDC 2285372'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D3CC04144A 2023
loop_
_audit_author_name
_audit_author_address
'P. Anbarasan'
;Indian Institute of Technology Madras
India
;
_audit_update_record             
;
2023-07-29 deposited with the CCDC.	2024-05-01 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         'C21 H14 Br N O'
_chemical_formula_sum            'C21 H14 Br N O'
_chemical_formula_weight         376.24

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      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                   8.6408(5)
_cell_length_b                   9.9341(5)
_cell_length_c                   10.3685(5)
_cell_angle_alpha                98.203(2)
_cell_angle_beta                 101.166(2)
_cell_angle_gamma                103.107(2)
_cell_volume                     834.05(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5672
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.21

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.470
_shelx_estimated_absorpt_T_min   0.612
_shelx_estimated_absorpt_T_max   0.756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.612
_exptl_absorpt_correction_T_max  0.756
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12302
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.041
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2924
_reflns_number_gt                2472
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0382P)²+0.3547P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0127(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2924
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0769
_refine_ls_wR_factor_gt          0.0727
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
Br1 Br 0.65114(3) 0.43470(3) 0.25377(3) 0.05911(15) Uani 1 1 d . . . . .
C1 C -0.4175(3) 0.1565(3) -0.3298(2) 0.0444(6) Uani 1 1 d . . . . .
H1 H -0.5292 0.1167 -0.3439 0.053 Uiso 1 1 calc R U . . .
C2 C -0.3500(3) 0.2004(3) -0.4305(3) 0.0519(7) Uani 1 1 d . . . . .
H2 H -0.4176 0.1900 -0.5148 0.062 Uiso 1 1 calc R U . . .
C3 C -0.1813(3) 0.2610(3) -0.4101(3) 0.0484(6) Uani 1 1 d . . . . .
H3 H -0.1398 0.2902 -0.4808 0.058 Uiso 1 1 calc R U . . .
C4 C -0.0768(3) 0.2776(2) -0.2875(2) 0.0397(5) Uani 1 1 d . . . . .
H4 H 0.0348 0.3169 -0.2749 0.048 Uiso 1 1 calc R U . . .
C5 C -0.1417(3) 0.2344(2) -0.1818(2) 0.0321(5) Uani 1 1 d . . . . .
C6 C -0.0707(2) 0.2314(2) -0.0460(2) 0.0298(5) Uani 1 1 d . . . . .
C7 C -0.1989(2) 0.1709(2) 0.0081(2) 0.0299(5) Uani 1 1 d . . . . .
C8 C -0.3116(3) 0.1741(2) -0.2050(2) 0.0328(5) Uani 1 1 d . . . . .
C9 C 0.1062(2) 0.2782(2) 0.0172(2) 0.0301(5) Uani 1 1 d . . . . .
C10 C 0.1933(3) 0.4172(2) 0.0307(2) 0.0368(5) Uani 1 1 d . . . . .
H10 H 0.1414 0.4797 -0.0067 0.044 Uiso 1 1 calc R U . . .
C11 C 0.3556(3) 0.4647(2) 0.0987(2) 0.0411(6) Uani 1 1 d . . . . .
H11 H 0.4122 0.5585 0.1086 0.049 Uiso 1 1 calc R U . . .
C12 C 0.4321(3) 0.3706(2) 0.1516(2) 0.0360(5) Uani 1 1 d . . . . .
C13 C 0.3519(3) 0.2307(2) 0.1348(2) 0.0387(5) Uani 1 1 d . . . . .
H13 H 0.4060 0.1675 0.1681 0.046 Uiso 1 1 calc R U . . .
C14 C 0.1896(3) 0.1859(2) 0.0675(2) 0.0352(5) Uani 1 1 d . . . . .
H14 H 0.1347 0.0914 0.0556 0.042 Uiso 1 1 calc R U . . .
C15 C -0.2061(2) 0.1283(2) 0.1362(2) 0.0320(5) Uani 1 1 d . . . . .
C16 C -0.0597(3) 0.1770(2) 0.2505(2) 0.0320(5) Uani 1 1 d . . . . .
C17 C 0.0277(3) 0.3175(2) 0.2912(2) 0.0345(5) Uani 1 1 d . . . . .
H17 H -0.0062 0.3852 0.2478 0.041 Uiso 1 1 calc R U . . .
C18 C 0.1648(3) 0.3569(3) 0.3957(2) 0.0435(6) Uani 1 1 d . . . . .
H18 H 0.2218 0.4514 0.4239 0.052 Uiso 1 1 calc R U . . .
C19 C 0.2174(3) 0.2569(3) 0.4584(3) 0.0510(7) Uani 1 1 d . . . . .
H19 H 0.3114 0.2835 0.5274 0.061 Uiso 1 1 calc R U . . .
C20 C 0.1306(3) 0.1170(3) 0.4191(3) 0.0532(7) Uani 1 1 d . . . . .
H20 H 0.1661 0.0493 0.4615 0.064 Uiso 1 1 calc R U . . .
C21 C -0.0084(3) 0.0777(3) 0.3169(2) 0.0433(6) Uani 1 1 d . . . . .
H21 H -0.0683 -0.0162 0.2923 0.052 Uiso 1 1 calc R U . . .
N1 N -0.3428(2) 0.1379(2) -0.08928(19) 0.0345(4) Uani 1 1 d . . . . .
O1 O -0.33070(19) 0.04688(18) 0.14752(17) 0.0467(4) Uani 1 1 d . . . . .
H1N H -0.429(3) 0.097(3) -0.080(2) 0.036(7) 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 C12 1.896(2) . ?
C1 C2 1.367(4) . ?
C1 C8 1.395(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.407(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.401(3) . ?
C4 H4 0.9300 . ?
C5 C8 1.412(3) . ?
C5 C6 1.431(3) . ?
C6 C7 1.392(3) . ?
C6 C9 1.478(3) . ?
C7 N1 1.381(3) . ?
C7 C15 1.459(3) . ?
C8 N1 1.359(3) . ?
C9 C14 1.386(3) . ?
C9 C10 1.388(3) . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C13 C14 1.378(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O1 1.228(2) . ?
C15 C16 1.489(3) . ?
C16 C21 1.385(3) . ?
C16 C17 1.388(3) . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
N1 H1N 0.79(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
C2 C1 C8 117.1(2) . . ?
C2 C1 H1 121.4 . . ?
C8 C1 H1 121.4 . . ?
C1 C2 C3 121.8(2) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C8 119.1(2) . . ?
C4 C5 C6 133.6(2) . . ?
C8 C5 C6 107.25(18) . . ?
C7 C6 C5 106.44(18) . . ?
C7 C6 C9 128.72(19) . . ?
C5 C6 C9 124.78(18) . . ?
N1 C7 C6 108.64(18) . . ?
N1 C7 C15 117.83(18) . . ?
C6 C7 C15 133.31(19) . . ?
N1 C8 C1 130.0(2) . . ?
N1 C8 C5 107.76(18) . . ?
C1 C8 C5 122.2(2) . . ?
C14 C9 C10 117.87(19) . . ?
C14 C9 C6 121.29(18) . . ?
C10 C9 C6 120.82(19) . . ?
C11 C10 C9 121.3(2) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C12 C11 C10 118.8(2) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 Br1 118.72(17) . . ?
C11 C12 Br1 119.79(16) . . ?
C12 C13 C14 118.6(2) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C13 C14 C9 121.7(2) . . ?
C13 C14 H14 119.1 . . ?
C9 C14 H14 119.1 . . ?
O1 C15 C7 119.73(19) . . ?
O1 C15 C16 120.10(19) . . ?
C7 C15 C16 120.08(17) . . ?
C21 C16 C17 119.2(2) . . ?
C21 C16 C15 118.48(19) . . ?
C17 C16 C15 122.31(19) . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C16 120.5(2) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
C8 N1 C7 109.90(18) . . ?
C8 N1 H1N 125.3(17) . . ?
C7 N1 H1N 124.5(17) . . ?

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
C8 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C8 0.6(3) . . . . ?
C3 C4 C5 C6 177.5(2) . . . . ?
C4 C5 C6 C7 -177.6(2) . . . . ?
C8 C5 C6 C7 -0.4(2) . . . . ?
C4 C5 C6 C9 -0.3(4) . . . . ?
C8 C5 C6 C9 176.82(19) . . . . ?
C5 C6 C7 N1 0.0(2) . . . . ?
C9 C6 C7 N1 -177.14(19) . . . . ?
C5 C6 C7 C15 174.2(2) . . . . ?
C9 C6 C7 C15 -2.9(4) . . . . ?
C2 C1 C8 N1 -178.3(2) . . . . ?
C2 C1 C8 C5 0.0(3) . . . . ?
C4 C5 C8 N1 178.38(19) . . . . ?
C6 C5 C8 N1 0.7(2) . . . . ?
C4 C5 C8 C1 -0.3(3) . . . . ?
C6 C5 C8 C1 -177.9(2) . . . . ?
C7 C6 C9 C14 57.5(3) . . . . ?
C5 C6 C9 C14 -119.2(2) . . . . ?
C7 C6 C9 C10 -121.0(3) . . . . ?
C5 C6 C9 C10 62.4(3) . . . . ?
C14 C9 C10 C11 -3.6(3) . . . . ?
C6 C9 C10 C11 174.9(2) . . . . ?
C9 C10 C11 C12 1.2(4) . . . . ?
C10 C11 C12 C13 1.9(4) . . . . ?
C10 C11 C12 Br1 -176.59(18) . . . . ?
C11 C12 C13 C14 -2.4(4) . . . . ?
Br1 C12 C13 C14 176.08(17) . . . . ?
C12 C13 C14 C9 -0.1(3) . . . . ?
C10 C9 C14 C13 3.0(3) . . . . ?
C6 C9 C14 C13 -175.4(2) . . . . ?
N1 C7 C15 O1 11.4(3) . . . . ?
C6 C7 C15 O1 -162.4(2) . . . . ?
N1 C7 C15 C16 -172.06(19) . . . . ?
C6 C7 C15 C16 14.1(4) . . . . ?
O1 C15 C16 C21 47.3(3) . . . . ?
C7 C15 C16 C21 -129.2(2) . . . . ?
O1 C15 C16 C17 -133.7(2) . . . . ?
C7 C15 C16 C17 49.8(3) . . . . ?
C21 C16 C17 C18 0.6(3) . . . . ?
C15 C16 C17 C18 -178.5(2) . . . . ?
C16 C17 C18 C19 1.3(4) . . . . ?
C17 C18 C19 C20 -1.6(4) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
C19 C20 C21 C16 1.8(4) . . . . ?
C17 C16 C21 C20 -2.1(4) . . . . ?
C15 C16 C21 C20 177.0(2) . . . . ?
C1 C8 N1 C7 177.7(2) . . . . ?
C5 C8 N1 C7 -0.8(2) . . . . ?
C6 C7 N1 C8 0.5(2) . . . . ?
C15 C7 N1 C8 -174.75(19) . . . . ?

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.053



