# Supplementary Information (SI) for Journal of Materials Chemistry B.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2468350'
loop_
_audit_author_name
_audit_author_address
'Ann Chippindale'
;University of Reading
United Kingdom
;
_audit_update_record             
;
2025-06-30 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;


#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   12.35473(14)
_cell_length_b                   38.9932(5)
_cell_length_c                   5.33318(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2569.26(5)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n 21 a '
_symmetry_space_group_name_Hall  'P -2ac -2n'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,y,-z+1/2
-x+1/2,y+1/2,z+1/2
-x,y+1/2,-z

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'
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'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C11.38 H8.75 Cl0.88 N2.62 O2.62 
# Dc =      0.66 Fooo =    525.00 Mu =     12.05 M =    255.23
# Found Formula = C26 H20 Cl2 N6 O6 
# Dc =      1.51 FOOO =   1200.00 Mu =     27.54 M =    583.39

_chemical_formula_sum            'C13 H10 Cl N3 O3'
_chemical_formula_moiety         'C7 H4 Cl N O2, C6 H6 N2 O'
_chemical_compound_source        .
_chemical_formula_weight         291.69


_cell_measurement_reflns_used    26466
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      76.30
_cell_measurement_temperature    100

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.023
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_max          0.117

_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    2.754

# Sheldrick geometric approximatio 0.80 0.94 
# No experimental values of Tmin/max available 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.94
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_device       Area
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       
; 
 'XtaLAB Synergy, Dualflex,HyPix, (Rigaku, 2021) 
;
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2021) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2021) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      100
_diffrn_reflns_number            26466
_diffrn_reflns_av_unetI/netI     2.695
_reflns_number_total             4991
_diffrn_reflns_av_R_equivalents  0.045
# Number of reflections without Friedels Law is 4991 
# Number of reflections with Friedels Law is 2651 
# Theoretical number of reflections is about 2692 


_diffrn_reflns_theta_min         2.266
_diffrn_reflns_theta_max         76.296
_diffrn_measured_fraction_theta_max 0.971

_diffrn_reflns_theta_full        67.141
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       6
_reflns_limit_h_min              0
_reflns_limit_h_max              15
_reflns_limit_k_min              -46
_reflns_limit_k_max              48
_reflns_limit_l_min              0
_reflns_limit_l_max              6

_oxford_diffrn_Wilson_B_factor   2.57
_oxford_diffrn_Wilson_scale      0.40

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

_refine_diff_density_min         -0.22
_refine_diff_density_max         0.24


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

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     7
_refine_ls_number_parameters     384
_refine_ls_number_reflns         4991
_refine_ls_R_factor_ref          0.0368
_refine_ls_wR_factor_ref         0.0907
_refine_ls_goodness_of_fit_ref   0.9917
_refine_ls_shift/su_max          0.0067910
_refine_ls_shift/su_mean         0.0002313


# Computed with I/sigma = -10 
_reflns_number_all               4991
_refine_ls_R_factor_all          0.0368
_refine_ls_wR_factor_all         0.0907

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4668
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_gt          0.0888

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  0.495(10) # for 2260 Friedel pairs 
_oxford_Bijvoet_difference       0.495(5) # for 2260 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          0.499(12) # for 2340 Friedel pairs 
_refine_ls_abs_structure_Flack   0.495(5)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 2260 Friedel Pairs 
;

# 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 ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 1.33P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
Cl1 Cl 0.77793(5) 0.33518(4) 0.14717(13) 0.0360 1.0000 Uani . . . . . .
Cl12 Cl 0.54260(5) 0.27653(4) 0.29793(14) 0.0409 1.0000 Uani . . . . . .
O7 O 1.18898(14) 0.39857(6) -0.1134(3) 0.0260 1.0000 Uani . . . . . .
O11 O 1.27149(15) 0.44131(6) 0.1030(4) 0.0311 1.0000 Uani . . . . . .
O17 O 0.94788(14) 0.21319(6) 0.6056(3) 0.0277 1.0000 Uani . . . . . .
O19 O 1.03131(14) 0.16886(6) 0.4092(4) 0.0323 1.0000 Uani . . . . . .
O23 O 0.53873(13) 0.05538(6) -0.2713(3) 0.0265 1.0000 Uani . . . . . .
O32 O 0.72130(13) 0.05461(6) 0.2656(3) 0.0264 1.0000 Uani . . . . . .
N5 N 1.10767(16) 0.41789(7) 0.2316(4) 0.0250 1.0000 Uani D . . . . .
N20 N 0.87045(17) 0.19200(7) 0.2618(4) 0.0257 1.0000 Uani D . . . . .
N25 N 0.65399(17) 0.01349(7) -0.1500(4) 0.0259 1.0000 Uani D . . . . .
N29 N 0.44457(17) -0.03718(6) -0.8831(4) 0.0270 1.0000 Uani . . . . . .
N34 N 0.60680(17) 0.09667(6) 0.1452(4) 0.0257 1.0000 Uani D . . . . .
N38 N 0.81791(17) 0.14698(6) 0.8767(4) 0.0272 1.0000 Uani . . . . . .
C2 C 0.8985(2) 0.35439(7) 0.0516(5) 0.0280 1.0000 Uani . . . . . .
C3 C 0.9422(2) 0.37978(8) 0.2054(5) 0.0266 1.0000 Uani . . . . . .
C4 C 1.0409(2) 0.39281(7) 0.1307(4) 0.0247 1.0000 Uani . . . . . .
C6 C 1.19544(19) 0.42172(7) 0.0821(5) 0.0249 1.0000 Uani . . . . . .
C8 C 1.09204(19) 0.38089(7) -0.0840(4) 0.0245 1.0000 Uani . . . . . .
C9 C 1.0482(2) 0.35665(7) -0.2391(5) 0.0274 1.0000 Uani . . . . . .
C10 C 0.9479(2) 0.34324(7) -0.1678(5) 0.0307 1.0000 Uani . . . . . .
C13 C 0.6638(2) 0.25799(7) 0.4028(5) 0.0299 1.0000 Uani . . . . . .
C14 C 0.7119(2) 0.27103(8) 0.6178(5) 0.0317 1.0000 Uani . . . . . .
C15 C 0.8102(2) 0.25750(8) 0.7026(5) 0.0296 1.0000 Uani . . . . . .
C16 C 0.85331(19) 0.23117(7) 0.5604(5) 0.0262 1.0000 Uani . . . . . .
C18 C 0.9563(2) 0.18878(7) 0.4175(5) 0.0268 1.0000 Uani . . . . . .
C21 C 0.8039(2) 0.21828(7) 0.3485(5) 0.0249 1.0000 Uani . . . . . .
C22 C 0.7070(2) 0.23138(8) 0.2628(5) 0.0278 1.0000 Uani . . . . . .
C24 C 0.57601(19) 0.02615(7) -0.2978(4) 0.0229 1.0000 Uani . . . . . .
C26 C 0.53324(18) 0.00337(7) -0.5021(4) 0.0225 1.0000 Uani . . . . . .
C27 C 0.4417(2) 0.01426(8) -0.6344(5) 0.0271 1.0000 Uani . . . . . .
C28 C 0.4005(2) -0.00660(8) -0.8210(5) 0.0289 1.0000 Uani . . . . . .
C30 C 0.5330(2) -0.04695(7) -0.7565(5) 0.0246 1.0000 Uani . . . . . .
C31 C 0.57925(19) -0.02799(7) -0.5664(5) 0.0247 1.0000 Uani . . . . . .
C33 C 0.68430(19) 0.08410(7) 0.2909(4) 0.0228 1.0000 Uani . . . . . .
C35 C 0.72829(18) 0.10669(7) 0.4957(4) 0.0224 1.0000 Uani . . . . . .
C36 C 0.6833(2) 0.13830(7) 0.5586(5) 0.0257 1.0000 Uani . . . . . .
C37 C 0.7311(2) 0.15710(8) 0.7487(5) 0.0261 1.0000 Uani . . . . . .
C39 C 0.8601(2) 0.11631(8) 0.8160(5) 0.0294 1.0000 Uani . . . . . .
C40 C 0.8185(2) 0.09578(8) 0.6296(5) 0.0279 1.0000 Uani . . . . . .
H31 H 0.9054 0.3880 0.3498 0.0318 1.0000 Uiso R . . . . .
H51 H 1.098(3) 0.4330(7) 0.347(5) 0.0500 1.0000 Uiso D . . . . .
H91 H 1.0845 0.3493 -0.3866 0.0306 1.0000 Uiso R . . . . .
H101 H 0.9128 0.3266 -0.2691 0.0361 1.0000 Uiso R . . . . .
H141 H 0.6774 0.2890 0.7078 0.0363 1.0000 Uiso R . . . . .
H151 H 0.8467 0.2662 0.8459 0.0343 1.0000 Uiso R . . . . .
H201 H 0.859(3) 0.1789(7) 0.136(4) 0.0500 1.0000 Uiso D . . . . .
H221 H 0.6719 0.2228 0.1172 0.0313 1.0000 Uiso R . . . . .
H271 H 0.4082 0.0355 -0.5958 0.0300 1.0000 Uiso R . . . . .
H281 H 0.3386 0.0010 -0.9110 0.0338 1.0000 Uiso R . . . . .
H301 H 0.5653 -0.0683 -0.7999 0.0300 1.0000 Uiso R . . . . .
H311 H 0.6417 -0.0360 -0.4807 0.0282 1.0000 Uiso R . . . . .
H361 H 0.6220 0.1468 0.4710 0.0294 1.0000 Uiso R . . . . .
H371 H 0.6993 0.1785 0.7924 0.0299 1.0000 Uiso R . . . . .
H391 H 0.9210 0.1083 0.9077 0.0344 1.0000 Uiso R . . . . .
H401 H 0.8515 0.0744 0.5906 0.0340 1.0000 Uiso R . . . . .
H251 H 0.675(3) 0.0270(7) -0.032(4) 0.039(8) 1.0000 Uiso D . . . . .
H252 H 0.676(2) -0.0071(4) -0.173(6) 0.034(8) 1.0000 Uiso D . . . . .
H341 H 0.587(2) 0.1175(3) 0.146(5) 0.024(7) 1.0000 Uiso D . . . . .
H342 H 0.587(2) 0.0849(6) 0.019(4) 0.031(8) 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.994(3)
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
Cl1 . C2 . 1.743(3) yes
Cl12 . C13 . 1.755(3) yes
O7 . C6 . 1.381(3) yes
O7 . C8 . 1.391(3) yes
O11 . C6 . 1.216(3) yes
O17 . C16 . 1.384(3) yes
O17 . C18 . 1.387(3) yes
O19 . C18 . 1.210(3) yes
O23 . C24 . 1.238(3) yes
O32 . C33 . 1.245(3) yes
N5 . C4 . 1.388(3) yes
N5 . C6 . 1.354(3) yes
N5 . H51 . 0.861(10) no
N20 . C18 . 1.353(3) yes
N20 . C21 . 1.393(3) yes
N20 . H201 . 0.855(10) no
N25 . C24 . 1.339(3) yes
N25 . H251 . 0.861(10) no
N25 . H252 . 0.857(10) no
N29 . C28 . 1.352(3) yes
N29 . C30 . 1.339(3) yes
N34 . C33 . 1.327(3) yes
N34 . H341 . 0.849(9) no
N34 . H342 . 0.853(10) no
N38 . C37 . 1.331(3) yes
N38 . C39 . 1.344(3) yes
C2 . C3 . 1.395(4) yes
C2 . C10 . 1.389(4) yes
C3 . C4 . 1.379(4) yes
C3 . H31 . 0.950 no
C4 . C8 . 1.388(3) yes
C8 . C9 . 1.368(4) yes
C9 . C10 . 1.397(4) yes
C9 . H91 . 0.950 no
C10 . H101 . 0.950 no
C13 . C14 . 1.388(4) yes
C13 . C22 . 1.385(4) yes
C14 . C15 . 1.400(4) yes
C14 . H141 . 0.950 no
C15 . C16 . 1.383(4) yes
C15 . H151 . 0.950 no
C16 . C21 . 1.380(3) yes
C21 . C22 . 1.380(4) yes
C22 . H221 . 0.950 no
C24 . C26 . 1.502(3) yes
C26 . C27 . 1.399(3) yes
C26 . C31 . 1.392(3) yes
C27 . C28 . 1.382(4) yes
C27 . H271 . 0.950 no
C28 . H281 . 0.950 no
C30 . C31 . 1.379(4) yes
C30 . H301 . 0.950 no
C31 . H311 . 0.950 no
C33 . C35 . 1.505(3) yes
C35 . C36 . 1.393(3) yes
C35 . C40 . 1.390(3) yes
C36 . C37 . 1.383(4) yes
C36 . H361 . 0.950 no
C37 . H371 . 0.950 no
C39 . C40 . 1.376(4) yes
C39 . H391 . 0.950 no
C40 . H401 . 0.950 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
C6 . O7 . C8 . 106.77(18) yes
C16 . O17 . C18 . 106.56(18) yes
C4 . N5 . C6 . 109.0(2) yes
C4 . N5 . H51 . 133(2) no
C6 . N5 . H51 . 117(2) no
C18 . N20 . C21 . 109.1(2) yes
C18 . N20 . H201 . 124(3) no
C21 . N20 . H201 . 127(3) no
C24 . N25 . H251 . 115(2) no
C24 . N25 . H252 . 120(2) no
H251 . N25 . H252 . 126(3) no
C28 . N29 . C30 . 117.1(2) yes
C33 . N34 . H341 . 123.9(19) no
C33 . N34 . H342 . 118(2) no
H341 . N34 . H342 . 116(3) no
C37 . N38 . C39 . 116.9(2) yes
Cl1 . C2 . C3 . 117.7(2) yes
Cl1 . C2 . C10 . 119.1(2) yes
C3 . C2 . C10 . 123.2(2) yes
C2 . C3 . C4 . 115.7(2) yes
C2 . C3 . H31 . 122.0 no
C4 . C3 . H31 . 122.2 no
N5 . C4 . C3 . 132.3(2) yes
N5 . C4 . C8 . 106.6(2) yes
C3 . C4 . C8 . 121.2(2) yes
O7 . C6 . N5 . 109.0(2) yes
O7 . C6 . O11 . 121.6(2) yes
N5 . C6 . O11 . 129.3(2) yes
O7 . C8 . C4 . 108.6(2) yes
O7 . C8 . C9 . 128.0(2) yes
C4 . C8 . C9 . 123.3(2) yes
C8 . C9 . C10 . 116.5(2) yes
C8 . C9 . H91 . 121.4 no
C10 . C9 . H91 . 122.1 no
C9 . C10 . C2 . 120.1(2) yes
C9 . C10 . H101 . 120.4 no
C2 . C10 . H101 . 119.5 no
Cl12 . C13 . C14 . 118.5(2) yes
Cl12 . C13 . C22 . 117.7(2) yes
C14 . C13 . C22 . 123.7(2) yes
C13 . C14 . C15 . 120.0(2) yes
C13 . C14 . H141 . 119.7 no
C15 . C14 . H141 . 120.3 no
C14 . C15 . C16 . 115.9(2) yes
C14 . C15 . H151 . 122.4 no
C16 . C15 . H151 . 121.7 no
O17 . C16 . C15 . 127.3(2) yes
O17 . C16 . C21 . 109.4(2) yes
C15 . C16 . C21 . 123.3(2) yes
O17 . C18 . N20 . 108.8(2) yes
O17 . C18 . O19 . 121.6(2) yes
N20 . C18 . O19 . 129.6(2) yes
N20 . C21 . C16 . 106.2(2) yes
N20 . C21 . C22 . 132.4(2) yes
C16 . C21 . C22 . 121.4(2) yes
C13 . C22 . C21 . 115.6(2) yes
C13 . C22 . H221 . 122.0 no
C21 . C22 . H221 . 122.4 no
N25 . C24 . O23 . 122.7(2) yes
N25 . C24 . C26 . 117.5(2) yes
O23 . C24 . C26 . 119.8(2) yes
C24 . C26 . C27 . 118.1(2) yes
C24 . C26 . C31 . 123.7(2) yes
C27 . C26 . C31 . 118.2(2) yes
C26 . C27 . C28 . 118.8(2) yes
C26 . C27 . H271 . 120.5 no
C28 . C27 . H271 . 120.7 no
C27 . C28 . N29 . 123.1(2) yes
C27 . C28 . H281 . 118.4 no
N29 . C28 . H281 . 118.4 no
N29 . C30 . C31 . 123.8(2) yes
N29 . C30 . H301 . 117.9 no
C31 . C30 . H301 . 118.3 no
C26 . C31 . C30 . 118.9(2) yes
C26 . C31 . H311 . 120.1 no
C30 . C31 . H311 . 121.0 no
N34 . C33 . O32 . 122.9(2) yes
N34 . C33 . C35 . 118.0(2) yes
O32 . C33 . C35 . 119.1(2) yes
C33 . C35 . C36 . 123.3(2) yes
C33 . C35 . C40 . 118.9(2) yes
C36 . C35 . C40 . 117.8(2) yes
C35 . C36 . C37 . 118.4(2) yes
C35 . C36 . H361 . 120.5 no
C37 . C36 . H361 . 121.1 no
C36 . C37 . N38 . 124.2(2) yes
C36 . C37 . H371 . 117.9 no
N38 . C37 . H371 . 117.8 no
N38 . C39 . C40 . 123.1(2) yes
N38 . C39 . H391 . 118.5 no
C40 . C39 . H391 . 118.4 no
C35 . C40 . C39 . 119.5(2) yes
C35 . C40 . H401 . 120.0 no
C39 . C40 . H401 . 120.4 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N5 . H51 . N29 3_656 171(4) 0.861(10) 1.923(12) 2.777(4) yes
N20 . H201 . N38 1_554 173(4) 0.855(10) 1.929(11) 2.779(4) yes
C27 . H271 . O32 2_454 124 0.95 2.59 3.222(4) yes
C31 . H311 . O11 4_745 151 0.95 2.45 3.308(4) yes
C36 . H361 . O19 2_455 152 0.95 2.47 3.342(4) yes
N25 . H251 . O32 . 174(3) 0.861(10) 2.002(11) 2.860(4) yes
N25 . H252 . O11 4_745 162(3) 0.857(10) 2.146(14) 2.972(4) yes
N34 . H341 . O19 2_455 171(3) 0.849(9) 2.137(11) 2.980(4) yes
N34 . H342 . O23 . 178(3) 0.853(10) 2.017(10) 2.869(4) yes



_refine_special_details          
;
?
  Reflections are selected by the following conditions :-
  Minimum value of SQRTW        is   0.00
  Minimum value of RATIO        is  -3.00
;
####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2490051'
loop_
_audit_author_name
_audit_author_address
'Ann Chippindale'
;University of Reading
United Kingdom
;
_audit_update_record             
;
2025-09-21 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;


#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   11.93448(15)
_cell_length_b                   42.5963(5)
_cell_length_c                   5.05886(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2571.75(6)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n 21 a '
_symmetry_space_group_name_Hall  'P -2ac -2n'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,y,-z+1/2
-x+1/2,y+1/2,z+1/2
-x,y+1/2,-z

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'
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'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C6 H6 Cl0.50 N6 O6 
# Dc =      0.71 Fooo =    562.00 Mu =     10.15 M =    275.88
# Found Formula = C26 H20 Cl2 N6 O6 
# Dc =      1.51 FOOO =   1200.00 Mu =     27.52 M =    583.39

_chemical_formula_sum            'C13 H10 Cl N3 O3'
_chemical_formula_moiety         'C7 H4 Cl N O2, C6 H6 N2 O'
_chemical_compound_source        .
_chemical_formula_weight         291.69


_cell_measurement_reflns_used    24424
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      72.64
_cell_measurement_temperature    100

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.023
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_max          0.257

_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    2.752

# Sheldrick geometric approximatio 0.91 0.94 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.94
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_device       Area
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       
; 
 'XtaLAB Synergy, Dualflex,HyPix, (Rigaku, 2021) 
;
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2021) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2021) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      100
_diffrn_reflns_number            24424
_diffrn_reflns_av_unetI/netI     0.056
_reflns_number_total             4543
_diffrn_reflns_av_R_equivalents  0.040
# Number of reflections without Friedels Law is 4543 
# Number of reflections with Friedels Law is 2456 
# Theoretical number of reflections is about 2556 


_diffrn_reflns_theta_min         4.151
_diffrn_reflns_theta_max         72.644
_diffrn_measured_fraction_theta_max 0.949

_diffrn_reflns_theta_full        71.927
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       5
_reflns_limit_h_min              0
_reflns_limit_h_max              14
_reflns_limit_k_min              -50
_reflns_limit_k_max              52
_reflns_limit_l_min              0
_reflns_limit_l_max              6

_oxford_diffrn_Wilson_B_factor   1.60
_oxford_diffrn_Wilson_scale      0.40

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

_refine_diff_density_min         -0.19
_refine_diff_density_max         0.50


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

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     7
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4543
_refine_ls_R_factor_ref          0.0531
_refine_ls_wR_factor_ref         0.1277
_refine_ls_goodness_of_fit_ref   0.9574
_refine_ls_shift/su_max          0.0038030
_refine_ls_shift/su_mean         0.0004159


# Computed with I/sigma = -10 
_reflns_number_all               4543
_refine_ls_R_factor_all          0.0531
_refine_ls_wR_factor_all         0.1277

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4434
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_gt          0.1269


# 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 unk


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.07P)² + 4.86P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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
Cl1 Cl 0.20195(8) 0.00588(5) 0.1676(2) 0.0360 1.0000 Uani . . . . . .
Cl12 Cl 0.44543(8) 0.05842(5) 0.2845(2) 0.0341 1.0000 Uani . . . . . .
O7 O -0.2054(2) -0.06332(7) -0.0731(5) 0.0278 1.0000 Uani . . . . . .
O11 O -0.2753(2) -0.10401(8) 0.1655(7) 0.0379 1.0000 Uani . . . . . .
O18 O 0.0358(2) 0.12430(7) 0.5739(5) 0.0273 1.0000 Uani . . . . . .
O22 O -0.0391(2) 0.16588(8) 0.3523(7) 0.0352 1.0000 Uani . . . . . .
O23 O 0.2573(2) 0.30269(8) -0.1820(5) 0.0271 1.0000 Uani . . . . . .
O32 O 0.4824(2) 0.26021(8) 0.1907(5) 0.0265 1.0000 Uani . . . . . .
N5 N -0.1081(3) -0.07955(9) 0.2738(7) 0.0236 1.0000 Uani D . . . . .
N16 N 0.1286(3) 0.14249(9) 0.2262(7) 0.0233 1.0000 Uani D . . . . .
N25 N 0.2912(3) 0.30372(9) 0.2558(6) 0.0201 1.0000 Uani D . . . . .
N28 N 0.0526(3) 0.37749(8) 0.3166(6) 0.0232 1.0000 Uani . . . . . .
N34 N 0.4464(3) 0.25918(9) -0.2459(6) 0.0213 1.0000 Uani D . . . . .
N37 N 0.6822(3) 0.18547(8) -0.3151(7) 0.0246 1.0000 Uani . . . . . .
C2 C 0.0832(3) -0.01545(9) 0.0735(8) 0.0244 1.0000 Uani . . . . . .
C3 C 0.0507(3) -0.04023(11) 0.2341(7) 0.0237 1.0000 Uani . . . . . .
C4 C -0.0478(3) -0.05495(10) 0.1623(8) 0.0219 1.0000 Uani . . . . . .
C6 C -0.2021(3) -0.08462(10) 0.1329(9) 0.0276 1.0000 Uani . . . . . .
C8 C -0.1090(3) -0.04515(9) -0.0530(7) 0.0225 1.0000 Uani . . . . . .
C9 C -0.0775(3) -0.02080(10) -0.2157(7) 0.0251 1.0000 Uani . . . . . .
C10 C 0.0231(3) -0.00568(10) -0.1462(8) 0.0263 1.0000 Uani . . . . . .
C13 C 0.3240(3) 0.07807(9) 0.3896(8) 0.0261 1.0000 Uani . . . . . .
C14 C 0.2905(3) 0.10391(10) 0.2427(7) 0.0208 1.0000 Uani . . . . . .
C15 C 0.1905(3) 0.11755(10) 0.3242(8) 0.0214 1.0000 Uani . . . . . .
C17 C 0.0354(3) 0.14672(10) 0.3732(8) 0.0271 1.0000 Uani . . . . . .
C19 C 0.1326(3) 0.10648(9) 0.5399(8) 0.0246 1.0000 Uani . . . . . .
C20 C 0.1665(4) 0.08123(10) 0.6891(8) 0.0277 1.0000 Uani . . . . . .
C21 C 0.2667(3) 0.06676(9) 0.6074(8) 0.0275 1.0000 Uani . . . . . .
C24 C 0.2333(3) 0.31210(9) 0.0449(7) 0.0198 1.0000 Uani . . . . . .
C26 C 0.1372(3) 0.33446(9) 0.0827(7) 0.0192 1.0000 Uani . . . . . .
C27 C 0.1371(3) 0.35627(10) 0.2828(7) 0.0204 1.0000 Uani . . . . . .
C29 C -0.0319(3) 0.37644(9) 0.1480(8) 0.0238 1.0000 Uani . . . . . .
C30 C -0.0376(3) 0.35543(10) -0.0615(8) 0.0267 1.0000 Uani . . . . . .
C31 C 0.0482(3) 0.33429(9) -0.0966(7) 0.0215 1.0000 Uani . . . . . .
C33 C 0.5041(3) 0.25066(9) -0.0361(7) 0.0202 1.0000 Uani . . . . . .
C35 C 0.6005(3) 0.22840(9) -0.0766(7) 0.0185 1.0000 Uani . . . . . .
C36 C 0.6008(3) 0.20642(9) -0.2792(7) 0.0190 1.0000 Uani . . . . . .
C38 C 0.7692(3) 0.18633(10) -0.1475(8) 0.0261 1.0000 Uani . . . . . .
C39 C 0.7759(3) 0.20710(10) 0.0615(8) 0.0251 1.0000 Uani . . . . . .
C40 C 0.6885(3) 0.22841(9) 0.0991(7) 0.0217 1.0000 Uani . . . . . .
H31 H 0.0931 -0.0464 0.3837 0.0284 1.0000 Uiso R . . . . .
H91 H -0.1207 -0.0144 -0.3646 0.0300 1.0000 Uiso R . . . . .
H101 H 0.0499 0.0116 -0.2502 0.0315 1.0000 Uiso R . . . . .
H141 H 0.3327 0.1119 0.0975 0.0250 1.0000 Uiso R . . . . .
H201 H 0.1251 0.0743 0.8377 0.0332 1.0000 Uiso R . . . . .
H211 H 0.2950 0.0494 0.7021 0.0330 1.0000 Uiso R . . . . .
H271 H 0.1984 0.3568 0.4028 0.0244 1.0000 Uiso R . . . . .
H291 H -0.0919 0.3911 0.1711 0.0285 1.0000 Uiso R . . . . .
H301 H -0.0998 0.3559 -0.1787 0.0321 1.0000 Uiso R . . . . .
H311 H 0.0469 0.3201 -0.2399 0.0257 1.0000 Uiso R . . . . .
H361 H 0.5394 0.2065 -0.3988 0.0228 1.0000 Uiso R . . . . .
H381 H 0.8290 0.1722 -0.1737 0.0312 1.0000 Uiso R . . . . .
H391 H 0.8386 0.2071 0.1770 0.0301 1.0000 Uiso R . . . . .
H401 H 0.6897 0.2429 0.2434 0.0260 1.0000 Uiso R . . . . .
H51 H -0.092(4) -0.0908(9) 0.407(5) 0.0296 1.0000 Uiso D . . . . .
H161 H 0.152(4) 0.1561(8) 0.116(7) 0.0272 1.0000 Uiso D . . . . .
H251 H 0.264(3) 0.3073(10) 0.408(4) 0.0234 1.0000 Uiso D . . . . .
H252 H 0.349(2) 0.2925(8) 0.232(9) 0.0234 1.0000 Uiso D . . . . .
H341 H 0.396(3) 0.2727(8) -0.209(8) 0.0252 1.0000 Uiso D . . . . .
H342 H 0.465(3) 0.2532(10) -0.400(3) 0.0252 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.143(6)

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33

1 0.297(18) 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000
2 0.703(18) 1.0000 0.0000 0.0000 0.0000 -1.0000 0.0000 0.0000 0.0000 -1.0000
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
Cl1 . C2 . 1.749(4) yes
Cl12 . C13 . 1.756(4) yes
O7 . C6 . 1.382(5) yes
O7 . C8 . 1.390(4) yes
O11 . C6 . 1.213(5) yes
O18 . C17 . 1.394(5) yes
O18 . C19 . 1.393(4) yes
O22 . C17 . 1.211(5) yes
O23 . C24 . 1.249(4) yes
O32 . C33 . 1.245(5) yes
N5 . C4 . 1.391(5) yes
N5 . C6 . 1.347(5) yes
N5 . H51 . 0.8500(10) no
N16 . C15 . 1.385(5) yes
N16 . C17 . 1.350(5) yes
N16 . H161 . 0.8499(10) no
N25 . C24 . 1.320(5) yes
N25 . H251 . 0.8500(10) no
N25 . H252 . 0.8500(10) no
N28 . C27 . 1.366(5) yes
N28 . C29 . 1.321(5) yes
N34 . C33 . 1.316(5) yes
N34 . H341 . 0.8500(10) no
N34 . H342 . 0.8500(10) no
N37 . C36 . 1.332(5) yes
N37 . C38 . 1.341(5) yes
C2 . C3 . 1.388(6) yes
C2 . C10 . 1.387(6) yes
C3 . C4 . 1.380(6) yes
C3 . H31 . 0.948 no
C4 . C8 . 1.376(5) yes
C8 . C9 . 1.377(6) yes
C9 . C10 . 1.406(6) yes
C9 . H91 . 0.953 no
C10 . H101 . 0.958 no
C13 . C14 . 1.387(5) yes
C13 . C21 . 1.384(6) yes
C14 . C15 . 1.390(5) yes
C14 . H141 . 0.954 no
C15 . C19 . 1.375(6) yes
C19 . C20 . 1.375(6) yes
C20 . C21 . 1.407(6) yes
C20 . H201 . 0.947 no
C21 . H211 . 0.943 no
C24 . C26 . 1.503(5) yes
C26 . C27 . 1.374(5) yes
C26 . C31 . 1.398(5) yes
C27 . H271 . 0.950 no
C29 . C30 . 1.389(6) yes
C29 . H291 . 0.956 no
C30 . C31 . 1.375(5) yes
C30 . H301 . 0.950 no
C31 . H311 . 0.944 no
C33 . C35 . 1.505(5) yes
C35 . C36 . 1.388(5) yes
C35 . C40 . 1.376(5) yes
C36 . H361 . 0.950 no
C38 . C39 . 1.381(6) yes
C38 . H381 . 0.944 no
C39 . C40 . 1.396(5) yes
C39 . H391 . 0.949 no
C40 . H401 . 0.957 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
C6 . O7 . C8 . 106.7(3) yes
C17 . O18 . C19 . 106.6(3) yes
C4 . N5 . C6 . 109.7(3) yes
C4 . N5 . H51 . 129(3) no
C6 . N5 . H51 . 121(3) no
C15 . N16 . C17 . 110.1(3) yes
C15 . N16 . H161 . 126(3) no
C17 . N16 . H161 . 122(3) no
C24 . N25 . H251 . 119(3) no
C24 . N25 . H252 . 118(3) no
H251 . N25 . H252 . 123(4) no
C27 . N28 . C29 . 117.4(3) yes
C33 . N34 . H341 . 112(3) no
C33 . N34 . H342 . 121(3) no
H341 . N34 . H342 . 126(4) no
C36 . N37 . C38 . 117.4(3) yes
Cl1 . C2 . C3 . 117.5(3) yes
Cl1 . C2 . C10 . 118.8(3) yes
C3 . C2 . C10 . 123.5(4) yes
C2 . C3 . C4 . 115.4(4) yes
C2 . C3 . H31 . 121.9 no
C4 . C3 . H31 . 122.7 no
N5 . C4 . C3 . 132.5(4) yes
N5 . C4 . C8 . 105.9(3) yes
C3 . C4 . C8 . 121.5(4) yes
O7 . C6 . N5 . 108.5(3) yes
O7 . C6 . O11 . 121.9(4) yes
N5 . C6 . O11 . 129.5(4) yes
O7 . C8 . C4 . 109.2(3) yes
O7 . C8 . C9 . 127.0(3) yes
C4 . C8 . C9 . 123.8(4) yes
C8 . C9 . C10 . 115.4(3) yes
C8 . C9 . H91 . 122.7 no
C10 . C9 . H91 . 121.9 no
C9 . C10 . C2 . 120.3(3) yes
C9 . C10 . H101 . 119.9 no
C2 . C10 . H101 . 119.8 no
Cl12 . C13 . C14 . 117.0(3) yes
Cl12 . C13 . C21 . 118.9(3) yes
C14 . C13 . C21 . 124.1(4) yes
C13 . C14 . C15 . 114.9(3) yes
C13 . C14 . H141 . 123.0 no
C15 . C14 . H141 . 122.1 no
C14 . C15 . N16 . 132.2(4) yes
C14 . C15 . C19 . 121.6(4) yes
N16 . C15 . C19 . 106.3(3) yes
O18 . C17 . N16 . 107.9(3) yes
O18 . C17 . O22 . 121.8(4) yes
N16 . C17 . O22 . 130.3(4) yes
O18 . C19 . C15 . 109.1(3) yes
O18 . C19 . C20 . 127.1(4) yes
C15 . C19 . C20 . 123.8(4) yes
C19 . C20 . C21 . 115.6(4) yes
C19 . C20 . H201 . 121.8 no
C21 . C20 . H201 . 122.6 no
C20 . C21 . C13 . 120.1(3) yes
C20 . C21 . H211 . 119.9 no
C13 . C21 . H211 . 120.0 no
N25 . C24 . O23 . 122.4(3) yes
N25 . C24 . C26 . 117.9(3) yes
O23 . C24 . C26 . 119.7(3) yes
C24 . C26 . C27 . 121.5(3) yes
C24 . C26 . C31 . 119.6(3) yes
C27 . C26 . C31 . 118.8(3) yes
C26 . C27 . N28 . 122.7(3) yes
C26 . C27 . H271 . 119.1 no
N28 . C27 . H271 . 118.1 no
N28 . C29 . C30 . 123.5(3) yes
N28 . C29 . H291 . 118.0 no
C30 . C29 . H291 . 118.5 no
C29 . C30 . C31 . 118.9(3) yes
C29 . C30 . H301 . 120.1 no
C31 . C30 . H301 . 121.0 no
C26 . C31 . C30 . 118.6(3) yes
C26 . C31 . H311 . 120.9 no
C30 . C31 . H311 . 120.4 no
N34 . C33 . O32 . 123.0(3) yes
N34 . C33 . C35 . 117.6(3) yes
O32 . C33 . C35 . 119.4(3) yes
C33 . C35 . C36 . 121.8(3) yes
C33 . C35 . C40 . 119.7(3) yes
C36 . C35 . C40 . 118.4(3) yes
C35 . C36 . N37 . 123.7(3) yes
C35 . C36 . H361 . 117.7 no
N37 . C36 . H361 . 118.7 no
N37 . C38 . C39 . 123.2(3) yes
N37 . C38 . H381 . 118.7 no
C39 . C38 . H381 . 118.2 no
C38 . C39 . C40 . 118.5(3) yes
C38 . C39 . H391 . 121.2 no
C40 . C39 . H391 . 120.3 no
C39 . C40 . C35 . 118.9(3) yes
C39 . C40 . H401 . 120.9 no
C35 . C40 . H401 . 120.3 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C30 . H301 . O11 3_454 135 0.95 2.40 3.143(5) yes
C39 . H391 . O22 1_655 134 0.95 2.45 3.181(5) yes
N5 . H51 . N28 4_546 172(4) 0.8500(10) 1.999(8) 2.843(5) yes
N16 . H161 . N37 2_454 169(4) 0.8499(10) 2.003(9) 2.843(5) yes
N25 . H251 . O23 1_556 154(4) 0.8500(10) 2.086(19) 2.873(5) yes
N25 . H252 . O32 . 173(4) 0.8499(10) 2.112(7) 2.958(5) yes
N34 . H341 . O23 . 169(4) 0.8500(10) 2.099(9) 2.938(5) yes
N34 . H342 . O32 1_554 152(4) 0.8500(10) 2.10(2) 2.882(5) yes



_refine_special_details          
;
?
  Reflections are selected by the following conditions :-
  Minimum value of SQRTW        is   0.00
  Minimum value of RATIO        is  -3.00
;
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
