# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_kel1707SNQ
_database_code_depnum_ccdc_archive 'CCDC 2219386'
loop_
_audit_author_name
_audit_author_address
'Anthony C. Willis'
;Australian National University
Australia
;
_audit_update_record             
;
2022-11-14 deposited with the CCDC.	2023-01-31 downloaded from the CCDC.
;
_audit_creation_date             17-09-29
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'Z:\kel1707SNQ\Tony_kel1707SNQ_da At 9:28 on '
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   9.36746(4)
_cell_length_b                   18.28656(9)
_cell_length_c                   25.06240(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4293.15(3)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a '
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,z
x+1/2,-y+1/2,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
x+1/2,y,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C25 H20 Br2 N2 O2 
# Dc =      1.67 Fooo =   2160.00 Mu =     49.97 M =    540.25
# Found Formula = C25 H20 Br2 N2 O2 
# Dc =      1.67 FOOO =   2160.00 Mu =     49.97 M =    540.25

_chemical_formula_sum            'C25 H20 Br2 N2 O2'
_chemical_formula_moiety         'C25 H20 Br2 N2 O2'
_chemical_compound_source        ' from U of Wollongong'
_chemical_formula_weight         540.25


_cell_measurement_reflns_used    47329
_cell_measurement_theta_min      4
_cell_measurement_theta_max      74
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.037
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_max          0.192

_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2160
_exptl_absorpt_coefficient_mu    4.997

# Sheldrick geometric approximatio 0.57 0.83 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)
(Release 29 April 2016; compiled 27 May 2016,16:53)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_T_max  0.83
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measurement_method       'ω scans'


# If a reference occurs more than once, delete the author 
# and date from subsequent references. 

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2017)'

_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            79188
_reflns_number_total             4349
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_sigmaI/netI    0.0376

# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4349 
# Theoretical number of reflections is about 8696 


_diffrn_reflns_theta_min         3.527
_diffrn_reflns_theta_max         73.853
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        73.853
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_reflns_limit_h_min              0
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              22
_reflns_limit_l_min              0
_reflns_limit_l_max              31

_oxford_diffrn_Wilson_B_factor   2.22
_oxford_diffrn_Wilson_scale      0.19

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.50
_refine_diff_density_max         0.53


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         4349
_refine_ls_number_restraints     0
_refine_ls_number_parameters     340
_oxford_refine_ls_R_factor_ref   0.0231
_refine_ls_wR_factor_ref         0.0556
_refine_ls_goodness_of_fit_ref   1.0299
_refine_ls_shift/su_max          0.0039529
_refine_ls_shift/su_mean         0.0002545


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4349
_refine_ls_R_factor_all          0.0231
_refine_ls_wR_factor_all         0.0556

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4249
_refine_ls_R_factor_gt           0.0226
_refine_ls_wR_factor_gt          0.0553

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    refxyz #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.02P)² + 4.39P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_special_details          
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               


The H atoms were all located in a difference map, but 
were repositioned geometrically. 
The H atoms were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98Å) and with
Uiso(H) in the range 1.2-1.5 times Ueq of the parent atom, 
after which the positions were refined without restraints
and the displacement parameters were held fixed. 


The largest peaks in the final difference electron density map
are located near Br(1) or halfway between bonded atoms.



;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Br1 Br 0.26425(2) 0.408187(9) 0.651954(7) 0.0258 1.0000 Uani . . . . . .
Br2 Br 0.70730(2) 1.030483(12) 0.498155(9) 0.0376 1.0000 Uani . . . . . .
O1 O 0.53105(12) 0.69534(6) 0.58628(4) 0.0193 1.0000 Uani . . . . . .
O2 O 0.53122(14) 0.82929(7) 0.66997(5) 0.0290 1.0000 Uani . . . . . .
N1 N 0.71275(14) 0.63167(7) 0.70198(5) 0.0178 1.0000 Uani . . . . . .
N2 N 0.87297(14) 0.76812(8) 0.62991(6) 0.0216 1.0000 Uani . . . . . .
C1 C 0.62545(16) 0.57184(8) 0.69359(6) 0.0175 1.0000 Uani . . . . . .
C2 C 0.60975(18) 0.50908(9) 0.72459(7) 0.0217 1.0000 Uani . . . . . .
C3 C 0.50279(19) 0.46061(9) 0.71069(7) 0.0228 1.0000 Uani . . . . . .
C4 C 0.41674(18) 0.47449(9) 0.66606(7) 0.0206 1.0000 Uani . . . . . .
C5 C 0.43320(17) 0.53560(9) 0.63402(6) 0.0191 1.0000 Uani . . . . . .
C6 C 0.53908(17) 0.58635(8) 0.64838(6) 0.0172 1.0000 Uani . . . . . .
C7 C 0.57996(16) 0.65782(8) 0.63010(6) 0.0161 1.0000 Uani . . . . . .
C8 C 0.68251(16) 0.68451(8) 0.66357(6) 0.0163 1.0000 Uani . . . . . .
C9 C 0.85172(17) 0.82794(8) 0.59822(6) 0.0172 1.0000 Uani . . . . . .
C10 C 0.94317(17) 0.85763(9) 0.55936(7) 0.0213 1.0000 Uani . . . . . .
C11 C 0.89581(18) 0.91712(9) 0.53064(7) 0.0226 1.0000 Uani . . . . . .
C12 C 0.76127(19) 0.94818(9) 0.53995(7) 0.0235 1.0000 Uani . . . . . .
C13 C 0.67050(19) 0.92065(9) 0.57813(7) 0.0238 1.0000 Uani . . . . . .
C14 C 0.71781(17) 0.86012(9) 0.60717(6) 0.0189 1.0000 Uani . . . . . .
C15 C 0.64707(18) 0.81954(9) 0.64913(6) 0.0198 1.0000 Uani . . . . . .
C16 C 0.75259(17) 0.75849(9) 0.66694(6) 0.0182 1.0000 Uani . . . . . .
C17 C 0.81249(18) 0.64217(10) 0.74300(7) 0.0232 1.0000 Uani . . . . . .
C18 C 0.8571(2) 0.70923(10) 0.75390(7) 0.0273 1.0000 Uani . . . . . .
C19 C 0.7944(2) 0.77417(10) 0.72573(7) 0.0273 1.0000 Uani . . . . . .
C20 C 0.38019(18) 0.71254(11) 0.58780(7) 0.0247 1.0000 Uani . . . . . .
C21 C 0.35193(18) 0.76999(9) 0.54716(7) 0.0232 1.0000 Uani . . . . . .
C22 C 0.2552(2) 0.76344(12) 0.50934(7) 0.0284 1.0000 Uani . . . . . .
C23 C 1.00694(17) 0.72809(9) 0.63406(7) 0.0226 1.0000 Uani . . . . . .
C24 C 0.9996(2) 0.65233(11) 0.61177(9) 0.0328 1.0000 Uani . . . . . .
C25 C 1.0493(3) 0.59464(12) 0.63680(13) 0.0489 1.0000 Uani . . . . . .
H21 H 0.669(2) 0.5008(11) 0.7546(9) 0.0250 1.0000 Uiso . . . . . .
H31 H 0.485(2) 0.4192(12) 0.7321(9) 0.0273 1.0000 Uiso . . . . . .
H51 H 0.374(2) 0.5434(11) 0.6041(8) 0.0227 1.0000 Uiso . . . . . .
H101 H 1.033(2) 0.8362(11) 0.5523(8) 0.0266 1.0000 Uiso . . . . . .
H111 H 0.954(2) 0.9366(12) 0.5050(8) 0.0280 1.0000 Uiso . . . . . .
H131 H 0.580(2) 0.9402(12) 0.5846(8) 0.0273 1.0000 Uiso . . . . . .
H171 H 0.844(2) 0.6000(12) 0.7593(9) 0.0284 1.0000 Uiso . . . . . .
H181 H 0.926(3) 0.7170(12) 0.7790(9) 0.0338 1.0000 Uiso . . . . . .
H191 H 0.859(3) 0.8164(13) 0.7268(9) 0.0339 1.0000 Uiso . . . . . .
H192 H 0.707(3) 0.7881(12) 0.7432(9) 0.0330 1.0000 Uiso . . . . . .
H201 H 0.356(2) 0.7308(12) 0.6221(9) 0.0307 1.0000 Uiso . . . . . .
H202 H 0.327(3) 0.6681(12) 0.5798(9) 0.0305 1.0000 Uiso . . . . . .
H211 H 0.409(2) 0.8147(12) 0.5505(9) 0.0289 1.0000 Uiso . . . . . .
H221 H 0.236(3) 0.8035(14) 0.4826(10) 0.0344 1.0000 Uiso . . . . . .
H222 H 0.201(3) 0.7186(13) 0.5072(9) 0.0337 1.0000 Uiso . . . . . .
H231 H 1.040(2) 0.7264(11) 0.6704(9) 0.0278 1.0000 Uiso . . . . . .
H232 H 1.081(2) 0.7562(11) 0.6149(8) 0.0272 1.0000 Uiso . . . . . .
H241 H 0.957(3) 0.6482(13) 0.5790(10) 0.0409 1.0000 Uiso . . . . . .
H251 H 1.094(3) 0.5996(15) 0.6725(12) 0.0599 1.0000 Uiso . . . . . .
H252 H 1.049(3) 0.5467(16) 0.6213(11) 0.0597 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.397(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . C4 . 1.9067(16) yes
Br2 . C12 . 1.9020(17) yes
O1 . C7 . 1.3736(18) yes
O1 . C20 . 1.4482(19) yes
O2 . C15 . 1.218(2) yes
N1 . C1 . 1.382(2) yes
N1 . C8 . 1.3930(19) yes
N1 . C17 . 1.402(2) yes
N2 . C9 . 1.366(2) yes
N2 . C16 . 1.471(2) yes
N2 . C23 . 1.457(2) yes
C1 . C2 . 1.394(2) yes
C1 . C6 . 1.417(2) yes
C2 . C3 . 1.382(2) yes
C2 . H21 . 0.95(2) no
C3 . C4 . 1.402(2) yes
C3 . H31 . 0.94(2) no
C4 . C5 . 1.385(2) yes
C5 . C6 . 1.405(2) yes
C5 . H51 . 0.94(2) no
C6 . C7 . 1.437(2) yes
C7 . C8 . 1.366(2) yes
C8 . C16 . 1.506(2) yes
C9 . C10 . 1.406(2) yes
C9 . C14 . 1.404(2) yes
C10 . C11 . 1.378(2) yes
C10 . H101 . 0.95(2) no
C11 . C12 . 1.402(2) yes
C11 . H111 . 0.92(2) no
C12 . C13 . 1.376(2) yes
C13 . C14 . 1.397(2) yes
C13 . H131 . 0.94(2) no
C14 . C15 . 1.448(2) yes
C15 . C16 . 1.557(2) yes
C16 . C19 . 1.551(2) yes
C17 . C18 . 1.324(3) yes
C17 . H171 . 0.92(2) no
C18 . C19 . 1.501(3) yes
C18 . H181 . 0.91(2) no
C19 . H191 . 0.98(2) no
C19 . H192 . 0.96(2) no
C20 . C21 . 1.487(2) yes
C20 . H201 . 0.95(2) no
C20 . H202 . 0.97(2) no
C21 . C22 . 1.316(3) yes
C21 . H211 . 0.98(2) no
C22 . H221 . 1.01(2) no
C22 . H222 . 0.96(2) no
C23 . C24 . 1.495(3) yes
C23 . H231 . 0.96(2) no
C23 . H232 . 0.99(2) no
C24 . C25 . 1.313(3) yes
C24 . H241 . 0.92(3) no
C25 . H251 . 0.99(3) no
C25 . H252 . 0.96(3) no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 . O1 . C20 . 114.39(12) yes
C1 . N1 . C8 . 108.89(13) yes
C1 . N1 . C17 . 127.88(14) yes
C8 . N1 . C17 . 123.17(14) yes
C9 . N2 . C16 . 110.55(13) yes
C9 . N2 . C23 . 124.70(13) yes
C16 . N2 . C23 . 123.73(13) yes
N1 . C1 . C2 . 129.03(15) yes
N1 . C1 . C6 . 108.13(13) yes
C2 . C1 . C6 . 122.65(15) yes
C1 . C2 . C3 . 117.65(15) yes
C1 . C2 . H21 . 120.8(12) no
C3 . C2 . H21 . 121.5(12) no
C2 . C3 . C4 . 120.12(15) yes
C2 . C3 . H31 . 120.0(13) no
C4 . C3 . H31 . 119.9(13) no
Br1 . C4 . C3 . 117.62(12) yes
Br1 . C4 . C5 . 119.28(13) yes
C3 . C4 . C5 . 123.01(15) yes
C4 . C5 . C6 . 117.59(15) yes
C4 . C5 . H51 . 121.3(12) no
C6 . C5 . H51 . 121.1(12) no
C1 . C6 . C5 . 118.94(14) yes
C1 . C6 . C7 . 105.84(13) yes
C5 . C6 . C7 . 135.02(15) yes
C6 . C7 . O1 . 128.34(14) yes
C6 . C7 . C8 . 108.47(13) yes
O1 . C7 . C8 . 123.17(14) yes
N1 . C8 . C7 . 108.64(13) yes
N1 . C8 . C16 . 119.72(13) yes
C7 . C8 . C16 . 131.47(14) yes
N2 . C9 . C10 . 128.54(15) yes
N2 . C9 . C14 . 111.89(14) yes
C10 . C9 . C14 . 119.56(15) yes
C9 . C10 . C11 . 118.06(15) yes
C9 . C10 . H101 . 120.9(13) no
C11 . C10 . H101 . 121.0(13) no
C10 . C11 . C12 . 121.51(15) yes
C10 . C11 . H111 . 118.8(14) no
C12 . C11 . H111 . 119.7(14) no
Br2 . C12 . C11 . 117.91(13) yes
Br2 . C12 . C13 . 120.56(13) yes
C11 . C12 . C13 . 121.54(16) yes
C12 . C13 . C14 . 117.15(15) yes
C12 . C13 . H131 . 122.8(13) no
C14 . C13 . H131 . 120.1(13) no
C9 . C14 . C13 . 122.17(15) yes
C9 . C14 . C15 . 108.08(14) yes
C13 . C14 . C15 . 129.75(15) yes
C14 . C15 . O2 . 130.14(16) yes
C14 . C15 . C16 . 106.58(13) yes
O2 . C15 . C16 . 123.23(15) yes
C15 . C16 . C8 . 110.58(13) yes
C15 . C16 . N2 . 102.71(12) yes
C8 . C16 . N2 . 113.98(13) yes
C15 . C16 . C19 . 107.47(14) yes
C8 . C16 . C19 . 109.23(13) yes
N2 . C16 . C19 . 112.54(14) yes
N1 . C17 . C18 . 119.24(16) yes
N1 . C17 . H171 . 114.8(14) no
C18 . C17 . H171 . 125.9(14) no
C17 . C18 . C19 . 120.79(16) yes
C17 . C18 . H181 . 120.7(14) no
C19 . C18 . H181 . 118.5(14) no
C16 . C19 . C18 . 113.54(15) yes
C16 . C19 . H191 . 109.2(13) no
C18 . C19 . H191 . 111.5(13) no
C16 . C19 . H192 . 105.4(14) no
C18 . C19 . H192 . 109.2(14) no
H191 . C19 . H192 . 107.8(19) no
O1 . C20 . C21 . 108.00(14) yes
O1 . C20 . H201 . 109.6(13) no
C21 . C20 . H201 . 109.2(13) no
O1 . C20 . H202 . 108.3(14) no
C21 . C20 . H202 . 110.9(13) no
H201 . C20 . H202 . 110.9(18) no
C20 . C21 . C22 . 123.46(18) yes
C20 . C21 . H211 . 115.8(13) no
C22 . C21 . H211 . 120.7(13) no
C21 . C22 . H221 . 122.3(14) no
C21 . C22 . H222 . 118.5(14) no
H221 . C22 . H222 . 119.2(19) no
N2 . C23 . C24 . 113.53(14) yes
N2 . C23 . H231 . 111.2(13) no
C24 . C23 . H231 . 109.8(13) no
N2 . C23 . H232 . 108.0(12) no
C24 . C23 . H232 . 109.4(12) no
H231 . C23 . H232 . 104.5(17) no
C23 . C24 . C25 . 123.3(2) yes
C23 . C24 . H241 . 115.6(15) no
C25 . C24 . H241 . 121.1(15) no
C24 . C25 . H251 . 120.5(17) no
C24 . C25 . H252 . 122.7(18) no
H251 . C25 . H252 . 117(2) no


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
C20 O1 C7 C6 62.8(2) . . . . no
C20 O1 C7 C8 -118.75(17) . . . . no
C7 O1 C20 C21 163.92(13) . . . . no
C8 N1 C1 C2 -174.05(16) . . . . no
C8 N1 C1 C6 0.86(17) . . . . no
C17 N1 C1 C2 3.2(3) . . . . no
C17 N1 C1 C6 178.11(15) . . . . no
C1 N1 C8 C7 -1.73(17) . . . . no
C1 N1 C8 C16 173.92(13) . . . . no
C17 N1 C8 C7 -179.13(14) . . . . no
C17 N1 C8 C16 -3.5(2) . . . . no
C1 N1 C17 C18 -161.07(16) . . . . no
C8 N1 C17 C18 15.8(2) . . . . no
C16 N2 C9 C10 177.21(16) . . . . no
C16 N2 C9 C14 -4.16(18) . . . . no
C23 N2 C9 C10 8.5(3) . . . . no
C23 N2 C9 C14 -172.91(15) . . . . no
C9 N2 C16 C8 124.16(14) . . . . no
C9 N2 C16 C15 4.52(17) . . . . no
C9 N2 C16 C19 -110.74(15) . . . . no
C23 N2 C16 C8 -66.96(19) . . . . no
C23 N2 C16 C15 173.41(14) . . . . no
C23 N2 C16 C19 58.1(2) . . . . no
C9 N2 C23 C24 -112.67(18) . . . . no
C16 N2 C23 C24 80.0(2) . . . . no
N1 C1 C2 C3 172.73(16) . . . . no
C6 C1 C2 C3 -1.5(2) . . . . no
N1 C1 C6 C5 -175.34(14) . . . . no
N1 C1 C6 C7 0.28(17) . . . . no
C2 C1 C6 C5 0.0(2) . . . . no
C2 C1 C6 C7 175.58(15) . . . . no
C1 C2 C3 C4 1.5(2) . . . . no
C2 C3 C4 Br1 -176.32(13) . . . . no
C2 C3 C4 C5 0.2(3) . . . . no
Br1 C4 C5 C6 174.70(12) . . . . no
C3 C4 C5 C6 -1.7(2) . . . . no
C4 C5 C6 C1 1.6(2) . . . . no
C4 C5 C6 C7 -172.40(17) . . . . no
C1 C6 C7 O1 177.34(14) . . . . no
C1 C6 C7 C8 -1.34(17) . . . . no
C5 C6 C7 O1 -8.1(3) . . . . no
C5 C6 C7 C8 173.23(17) . . . . no
O1 C7 C8 N1 -176.87(13) . . . . no
O1 C7 C8 C16 8.2(3) . . . . no
C6 C7 C8 N1 1.89(17) . . . . no
C6 C7 C8 C16 -173.06(15) . . . . no
N1 C8 C16 N2 101.76(16) . . . . no
N1 C8 C16 C15 -143.15(14) . . . . no
N1 C8 C16 C19 -25.09(19) . . . . no
C7 C8 C16 N2 -83.8(2) . . . . no
C7 C8 C16 C15 31.3(2) . . . . no
C7 C8 C16 C19 149.40(17) . . . . no
N2 C9 C10 C11 177.41(16) . . . . no
C14 C9 C10 C11 -1.1(2) . . . . no
N2 C9 C14 C13 -177.90(15) . . . . no
N2 C9 C14 C15 1.76(18) . . . . no
C10 C9 C14 C13 0.9(2) . . . . no
C10 C9 C14 C15 -179.47(14) . . . . no
C9 C10 C11 C12 0.7(3) . . . . no
C10 C11 C12 Br2 179.71(13) . . . . no
C10 C11 C12 C13 0.0(3) . . . . no
Br2 C12 C13 C14 180.00(13) . . . . no
C11 C12 C13 C14 -0.3(3) . . . . no
C12 C13 C14 C9 -0.2(2) . . . . no
C12 C13 C14 C15 -179.74(16) . . . . no
C9 C14 C15 O2 178.52(17) . . . . no
C9 C14 C15 C16 1.17(17) . . . . no
C13 C14 C15 O2 -1.9(3) . . . . no
C13 C14 C15 C16 -179.21(16) . . . . no
O2 C15 C16 N2 179.06(15) . . . . no
O2 C15 C16 C8 57.1(2) . . . . no
O2 C15 C16 C19 -62.1(2) . . . . no
C14 C15 C16 N2 -3.36(16) . . . . no
C14 C15 C16 C8 -125.34(14) . . . . no
C14 C15 C16 C19 115.53(14) . . . . no
N2 C16 C19 C18 -85.83(18) . . . . no
C8 C16 C19 C18 41.82(19) . . . . no
C15 C16 C19 C18 161.81(14) . . . . no
N1 C17 C18 C19 4.5(3) . . . . no
C17 C18 C19 C16 -34.2(2) . . . . no
O1 C20 C21 C22 125.64(18) . . . . no
N2 C23 C24 C25 -133.2(2) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Br1 O2 3.1538(13) . 3_545 no
Br1 C10 3.7083(17) . 3_645 no
O1 O2 3.2248(17) . . no
O1 C15 2.9700(19) . . no
O1 C22 3.274(2) . 4_566 no
O2 C20 3.286(2) . . no
O2 C7 3.3225(19) . . no
O2 C18 3.335(2) . 8_456 no
C1 C17 3.574(2) . 8_456 no
C5 C20 3.472(3) . . no
C6 C17 3.600(2) . 8_456 no
C8 C24 3.295(2) . . no
C9 C22 3.298(2) . 4_566 no
C10 C22 3.312(3) . 4_566 no
C15 C20 3.527(2) . . no
C17 C25 3.572(3) . . no
C18 C23 3.333(2) . . no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 29/09/17 at 09:48:48
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT BR   (    1 ,X'S,U'S)  UNTIL C    (   25 ) 
CONT H    (   21 ,X'S)  UNTIL H    (  252 ) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 29/09/17 at 09:48:48
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;


#===END

