# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_BB4Clcatechol
_database_code_depnum_ccdc_archive 'CCDC 1886022'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;The Australian National University
Australia
;
_audit_update_record             
;
2018-12-19 deposited with the CCDC.	2019-04-25 downloaded from the CCDC.
;
#==============================================================================
# start Validation Reply Form
_vrf_PLAT260_BB4Clcatechol       
;
PROBLEM: Large Average Ueq of Residue Including       O51      0.275 Check 
RESPONSE: This residue corresponds to the disordered catechol ring, and is
probably due to additional disorder positions that could not be modelled.
Several crystals were grown of macrocycle catechol complexes from several
different solvents and all suffered from severe disorder of the catechol guest.
This structure represents the best effort from all of these datasets.
;

_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. 
;

_refine_special_details          
; 
The structure crystallises in the centrosymmetric space group P-1, with the 
centre of inversion located in the centre of the BB4+ macrocycle (where the 
disordered catechol resides). Due to the difficulties of refining a highly 
disordered group across a centre of symmetry, the structure was refined in 
the non-centrosymmetric space group P1. The catechol group was modelled as 
disordered over two positions (s.o.f.: 0.50:0.50) and it was necessary to add 
restraints to the bond lengths and angles of the catechol group, as well its 
thermal and vibrational ellipsoid parameters to achieve a sensible refinement. 
Restraints were also added to the methanol C--O bond lengths. Even with the 
restraints on the catechol group, this still has large ellipsoids, probably 
indicating further positional disorder. Despite numerous attempts, it was 
not possible to model this further. 
;
_cell_length_a                   9.6750(3)
_cell_length_b                   10.7761(4)
_cell_length_c                   12.8860(4)
_cell_angle_alpha                101.486(3)
_cell_angle_beta                 100.639(3)
_cell_angle_gamma                112.862(3)
_cell_volume                     1160.97(8)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1 '
_symmetry_space_group_name_Hall  'P 1'

loop_
_symmetry_equiv_pos_as_xyz
x,y,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            1

_chemical_formula_sum            'C46 H54 Cl4 N4 O6'
_chemical_formula_moiety         'C36 H32 N4,  C6 H6 O2, 4(C H4 O), 4(Cl)'
_chemical_compound_source        synthesized
_chemical_formula_weight         900.77


_cell_measurement_reflns_used    12354
_cell_measurement_theta_min      4.61
_cell_measurement_theta_max      73.4
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.06
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_max          0.41

_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             474
_exptl_absorpt_coefficient_mu    2.726

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction Supernova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'CrysAlisPro, (Agilent, 2011'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            22221
_diffrn_reflns_av_unetI/netI     0.049
_reflns_number_total             4671
_diffrn_reflns_av_R_equivalents  0.044

_diffrn_reflns_theta_min         4.667
_diffrn_reflns_theta_max         73.966
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        72.487
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -12
_reflns_limit_h_max              11
_reflns_limit_k_min              -13
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   2.71
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.66
_refine_diff_density_max         1.86

# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     112
_refine_ls_number_parameters     550
_refine_ls_number_reflns         4654
_oxford_refine_ls_R_factor_ref   0.0723
_refine_ls_wR_factor_ref         0.2116
_refine_ls_goodness_of_fit_ref   0.9781
_refine_ls_shift/su_max          0.0083097
_refine_ls_shift/su_mean         0.0018436

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4655
_refine_ls_R_factor_all          0.0721
_refine_ls_wR_factor_all         0.2116

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4400
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_gt          0.2062

_chemical_absolute_configuration unk

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.17P)² + 0.99P] 
 ,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
N1 N -0.1083(8) 0.2867(6) 0.3885(5) 0.0280 1.0000 Uani . . . . . .
C2 C -0.1141(9) 0.3634(7) 0.4812(6) 0.0259 1.0000 Uani . . . . . .
C3 C 0.0042(9) 0.4182(7) 0.5782(6) 0.0268 1.0000 Uani . . . . . .
C4 C 0.1362(9) 0.3928(7) 0.5808(6) 0.0276 1.0000 Uani . . . . . .
C5 C 0.1324(9) 0.3022(7) 0.4831(6) 0.0304 1.0000 Uani . . . . . .
C6 C 0.0131(10) 0.2545(8) 0.3882(7) 0.0312 1.0000 Uani . . . . . .
N7 N 0.5407(8) 0.6091(6) 0.8569(5) 0.0250 1.0000 Uani . . . . . .
C8 C 0.5522(10) 0.5407(8) 0.7582(7) 0.0337 1.0000 Uani . . . . . .
C9 C 0.4178(10) 0.4651(8) 0.6711(6) 0.0300 1.0000 Uani . . . . . .
C10 C 0.2740(9) 0.4600(7) 0.6769(6) 0.0271 1.0000 Uani . . . . . .
C11 C 0.2680(10) 0.5235(9) 0.7815(7) 0.0343 1.0000 Uani . . . . . .
C12 C 0.3997(10) 0.6021(9) 0.8671(6) 0.0319 1.0000 Uani . . . . . .
C13 C 0.6884(8) 0.7037(8) 0.9504(6) 0.0283 1.0000 Uani . . . . . .
C14 C 0.7627(9) 0.8447(7) 0.9279(6) 0.0253 1.0000 Uani . . . . . .
C15 C 0.7148(10) 0.9464(8) 0.9569(6) 0.0313 1.0000 Uani . . . . . .
C16 C 0.7733(10) 1.0691(7) 0.9238(6) 0.0359 1.0000 Uani . . . . . .
C17 C 0.8779(9) 1.0879(7) 0.8622(6) 0.0278 1.0000 Uani . . . . . .
C18 C 0.9344(9) 0.9850(8) 0.8410(6) 0.0310 1.0000 Uani . . . . . .
C19 C 0.8756(9) 0.8650(8) 0.8731(7) 0.0338 1.0000 Uani . . . . . .
C20 C 0.9273(9) 1.2114(8) 0.8163(6) 0.0317 1.0000 Uani . . . . . .
N21 N 0.8080(8) 1.1724(6) 0.7080(5) 0.0259 1.0000 Uani . . . . . .
C22 C 0.6881(10) 1.2069(8) 0.7066(6) 0.0287 1.0000 Uani . . . . . .
C23 C 0.5614(9) 1.1504(8) 0.6105(6) 0.0286 1.0000 Uani . . . . . .
C24 C 0.5638(8) 1.0661(7) 0.5169(6) 0.0240 1.0000 Uani . . . . . .
C25 C 0.6928(10) 1.0384(8) 0.5194(6) 0.0325 1.0000 Uani . . . . . .
C26 C 0.8160(10) 1.0916(8) 0.6168(6) 0.0324 1.0000 Uani . . . . . .
N27 N 0.1607(8) 0.8465(6) 0.2370(5) 0.0276 1.0000 Uani . . . . . .
C28 C 0.2955(9) 0.8568(8) 0.2245(6) 0.0295 1.0000 Uani . . . . . .
C29 C 0.4319(9) 0.9277(8) 0.3157(6) 0.0287 1.0000 Uani . . . . . .
C30 C 0.4229(8) 0.9942(7) 0.4151(5) 0.0234 1.0000 Uani . . . . . .
C31 C 0.2784(9) 0.9854(7) 0.4252(6) 0.0289 1.0000 Uani . . . . . .
C32 C 0.1506(8) 0.9113(8) 0.3322(6) 0.0258 1.0000 Uani . . . . . .
C33 C 0.0133(9) 0.7540(7) 0.1464(6) 0.0279 1.0000 Uani . . . . . .
C34 C -0.0645(9) 0.6148(7) 0.1674(6) 0.0275 1.0000 Uani . . . . . .
C35 C -0.1765(9) 0.5904(7) 0.2250(6) 0.0278 1.0000 Uani . . . . . .
C36 C -0.2331(9) 0.4682(7) 0.2574(6) 0.0315 1.0000 Uani . . . . . .
C37 C -0.1804(9) 0.3686(7) 0.2306(5) 0.0268 1.0000 Uani . . . . . .
C38 C -0.0692(9) 0.3885(8) 0.1718(6) 0.0315 1.0000 Uani . . . . . .
C39 C -0.0147(10) 0.5076(8) 0.1389(6) 0.0338 1.0000 Uani . . . . . .
C40 C -0.2298(9) 0.2463(7) 0.2807(6) 0.0290 1.0000 Uani . . . . . .
Cl1 Cl -0.2320(4) -0.0908(2) 0.2527(2) 0.0370 1.0000 Uani . . . . . .
Cl2 Cl 0.5010(4) 0.3394(3) 0.4183(2) 0.0378 1.0000 Uani . . . . . .
Cl4 Cl 0.9300(4) 0.5456(2) 0.8388(2) 0.0356 1.0000 Uani . . . . . .
Cl3 Cl 0.1965(4) 0.1150(3) 0.6733(2) 0.0371 1.0000 Uani . . . . . .
O121 O 0.2506(10) 0.8028(8) 0.9649(6) 0.0599 1.0000 Uani D . . . . .
O111 O 0.1874(12) 0.1647(15) 0.2337(6) 0.1194 1.0000 Uani D . . . . .
C112 C 0.2024(19) 0.1486(18) 0.1274(9) 0.0946 1.0000 Uani D . . . . .
O101 O 0.4469(9) 0.6559(8) 0.1280(6) 0.0646 1.0000 Uani D . . . . .
C102 C 0.4070(15) 0.5441(12) 0.1742(15) 0.1120 1.0000 Uani D . . . . .
C122 C 0.2802(17) 0.8970(14) 0.9004(12) 0.0888 1.0000 Uani D . . . . .
C55 C 0.549(3) 0.7924(12) 0.6399(12) 0.2553 1.0000 Uani D U . . . .
C54 C 0.441(3) 0.8355(12) 0.6736(12) 0.2485 1.0000 Uani D U . . . .
C51 C 0.353(2) 0.6459(12) 0.4628(11) 0.2879 1.0000 Uani D U . . . .
C53 C 0.292(3) 0.7871(13) 0.6032(14) 0.2568 1.0000 Uani D U . . . .
C52 C 0.248(2) 0.6912(12) 0.4977(12) 0.2740 1.0000 Uani D U . . . .
C56 C 0.507(2) 0.6974(12) 0.5351(11) 0.2791 1.0000 Uani D U . . . .
O52 O 0.101(3) 0.6413(16) 0.4293(16) 0.2560 0.5000 Uani D U . . 1 .
O131 O 0.5050(9) 0.2463(15) 0.8653(6) 0.1352 1.0000 Uani D . . . . .
C132 C 0.4972(16) 0.3169(10) 0.9620(7) 0.0646 1.0000 Uani D . . . . .
O51 O 0.305(3) 0.5540(12) 0.3610(12) 0.3503 1.0000 Uani D U . . . .
O56 O 0.618(3) 0.6594(13) 0.5058(16) 0.2646 0.5000 Uani D U . . 2 .
H21 H -0.2036 0.3777 0.4777 0.0334 1.0000 Uiso R . . . . .
H31 H -0.0025 0.4724 0.6415 0.0316 1.0000 Uiso R . . . . .
H51 H 0.2129 0.2740 0.4846 0.0363 1.0000 Uiso R . . . . .
H61 H 0.0144 0.1994 0.3216 0.0405 1.0000 Uiso R . . . . .
H81 H 0.6467 0.5442 0.7507 0.0333 1.0000 Uiso R . . . . .
H91 H 0.4283 0.4210 0.6045 0.0353 1.0000 Uiso R . . . . .
H111 H 0.1731 0.5185 0.7920 0.0436 1.0000 Uiso R . . . . .
H121 H 0.3963 0.6515 0.9330 0.0367 1.0000 Uiso R . . . . .
H131 H 0.6641 0.7178 1.0214 0.0353 1.0000 Uiso R . . . . .
H132 H 0.7593 0.6602 0.9529 0.0352 1.0000 Uiso R . . . . .
H151 H 0.6446 0.9363 1.0007 0.0413 1.0000 Uiso R . . . . .
H161 H 0.7378 1.1378 0.9426 0.0398 1.0000 Uiso R . . . . .
H181 H 1.0109 0.9982 0.8036 0.0367 1.0000 Uiso R . . . . .
H191 H 0.9115 0.7970 0.8569 0.0395 1.0000 Uiso R . . . . .
H201 H 0.9295 1.2933 0.8653 0.0399 1.0000 Uiso R . . . . .
H202 H 1.0306 1.2351 0.8074 0.0400 1.0000 Uiso R . . . . .
H221 H 0.6898 1.2678 0.7705 0.0324 1.0000 Uiso R . . . . .
H231 H 0.4747 1.1663 0.6123 0.0352 1.0000 Uiso R . . . . .
H251 H 0.6979 0.9829 0.4543 0.0397 1.0000 Uiso R . . . . .
H261 H 0.9030 1.0717 0.6215 0.0354 1.0000 Uiso R . . . . .
H281 H 0.3018 0.8150 0.1566 0.0392 1.0000 Uiso R . . . . .
H291 H 0.5286 0.9343 0.3076 0.0344 1.0000 Uiso R . . . . .
H311 H 0.2697 1.0306 0.4930 0.0362 1.0000 Uiso R . . . . .
H321 H 0.0536 0.9056 0.3364 0.0375 1.0000 Uiso R . . . . .
H331 H -0.0564 0.7995 0.1441 0.0332 1.0000 Uiso R . . . . .
H332 H 0.0383 0.7418 0.0765 0.0333 1.0000 Uiso R . . . . .
H351 H -0.2153 0.6567 0.2420 0.0357 1.0000 Uiso R . . . . .
H361 H -0.3069 0.4549 0.2982 0.0386 1.0000 Uiso R . . . . .
H381 H -0.0321 0.3215 0.1562 0.0415 1.0000 Uiso R . . . . .
H391 H 0.0541 0.5172 0.0941 0.0366 1.0000 Uiso R . . . . .
H401 H -0.3283 0.2293 0.2961 0.0341 1.0000 Uiso R . . . . .
H402 H -0.2398 0.1614 0.2297 0.0339 1.0000 Uiso R . . . . .
H551 H 0.6488 0.8251 0.6860 0.2791 1.0000 Uiso R . . . . .
H541 H 0.4713 0.8986 0.7449 0.2671 1.0000 Uiso R . . . . .
H531 H 0.2220 0.8183 0.6261 0.2740 1.0000 Uiso R . . . . .
H1211 H 0.1551 0.7546 0.9522 0.0811 1.0000 Uiso R . . . . .
H1011 H 0.5216 0.7252 0.1759 0.1010 1.0000 Uiso R . . . . .
H1111 H 0.2764 0.2290 0.2786 0.1699 1.0000 Uiso R . . . . .
H1 H 0.4205 0.2111 0.8128 0.1590 1.0000 Uiso R . . . . .
H561 H 0.5791 0.6672 0.5108 0.2976 0.5000 Uiso R . . . 1 .
H521 H 0.1442 0.6571 0.4509 0.2906 0.5000 Uiso R . . . 2 .
H1021 H 0.3214 0.4602 0.1249 0.1233 1.0000 Uiso R . . . . .
H1022 H 0.3776 0.5764 0.2368 0.1233 1.0000 Uiso R . . . . .
H1023 H 0.4940 0.5253 0.1976 0.1233 1.0000 Uiso R . . . . .
H1321 H 0.5943 0.3539 1.0176 0.0725 1.0000 Uiso R . . . . .
H1322 H 0.4161 0.2560 0.9852 0.0725 1.0000 Uiso R . . . . .
H1323 H 0.4753 0.3923 0.9497 0.0725 1.0000 Uiso R . . . . .
H1221 H 0.3900 0.9510 0.9162 0.1210 1.0000 Uiso R . . . . .
H1222 H 0.2340 0.9580 0.9205 0.1210 1.0000 Uiso R . . . . .
H1223 H 0.2361 0.8480 0.8236 0.1210 1.0000 Uiso R . . . . .
H1121 H 0.1065 0.0788 0.0755 0.1203 1.0000 Uiso R . . . . .
H1122 H 0.2247 0.2374 0.1148 0.1203 1.0000 Uiso R . . . . .
H1123 H 0.2846 0.1236 0.1190 0.1203 1.0000 Uiso R . . . . .
H562 H 0.7089 0.6918 0.5508 0.3295 0.5000 Uiso R . . . 2 .
H522 H 0.0368 0.6688 0.4500 0.3243 0.5000 Uiso R . . . 1 .
H511 H 0.2121 0.5253 0.3200 0.4264 1.0000 Uiso R . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.0(2)

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
N1 . C2 . 1.334(9) yes
N1 . C6 . 1.348(10) yes
N1 . C40 . 1.504(9) yes
C2 . C3 . 1.369(10) yes
C2 . H21 . 0.932 no
C3 . C4 . 1.402(10) yes
C3 . H31 . 0.933 no
C4 . C5 . 1.416(10) yes
C4 . C10 . 1.455(9) yes
C5 . C6 . 1.363(11) yes
C5 . H51 . 0.937 no
C6 . H61 . 0.947 no
N7 . C8 . 1.384(10) yes
N7 . C12 . 1.370(10) yes
N7 . C13 . 1.508(9) yes
C8 . C9 . 1.375(11) yes
C8 . H81 . 0.924 no
C9 . C10 . 1.387(10) yes
C9 . H91 . 0.939 no
C10 . C11 . 1.407(10) yes
C11 . C12 . 1.352(11) yes
C11 . H111 . 0.936 no
C12 . H121 . 0.922 no
C13 . C14 . 1.521(10) yes
C13 . H131 . 0.984 no
C13 . H132 . 0.969 no
C14 . C15 . 1.361(10) yes
C14 . C19 . 1.378(10) yes
C15 . C16 . 1.408(11) yes
C15 . H151 . 0.949 no
C16 . C17 . 1.377(11) yes
C16 . H161 . 0.939 no
C17 . C18 . 1.418(10) yes
C17 . C20 . 1.508(10) yes
C18 . C19 . 1.377(11) yes
C18 . H181 . 0.936 no
C19 . H191 . 0.930 no
C20 . N21 . 1.501(8) yes
C20 . H201 . 0.968 no
C20 . H202 . 0.966 no
N21 . C22 . 1.347(9) yes
N21 . C26 . 1.350(10) yes
C22 . C23 . 1.401(10) yes
C22 . H221 . 0.938 no
C23 . C24 . 1.368(9) yes
C23 . H231 . 0.923 no
C24 . C25 . 1.388(10) yes
C24 . C30 . 1.514(8) yes
C25 . C26 . 1.398(10) yes
C25 . H251 . 0.950 no
C26 . H261 . 0.941 no
N27 . C28 . 1.308(10) yes
N27 . C32 . 1.325(9) yes
N27 . C33 . 1.486(8) yes
C28 . C29 . 1.412(10) yes
C28 . H281 . 0.925 no
C29 . C30 . 1.373(9) yes
C29 . H291 . 0.938 no
C30 . C31 . 1.396(10) yes
C31 . C32 . 1.382(9) yes
C31 . H311 . 0.947 no
C32 . H321 . 0.929 no
C33 . C34 . 1.500(10) yes
C33 . H331 . 0.975 no
C33 . H332 . 0.972 no
C34 . C35 . 1.396(10) yes
C34 . C39 . 1.425(10) yes
C35 . C36 . 1.397(9) yes
C35 . H351 . 0.936 no
C36 . C37 . 1.369(10) yes
C36 . H361 . 0.947 no
C37 . C38 . 1.402(9) yes
C37 . C40 . 1.531(10) yes
C38 . C39 . 1.370(11) yes
C38 . H381 . 0.927 no
C39 . H391 . 0.949 no
C40 . H401 . 0.963 no
C40 . H402 . 0.973 no
O121 . C122 . 1.414(8) yes
O121 . H1211 . 0.829 no
O111 . C112 . 1.389(9) yes
O111 . H1111 . 0.866 no
C112 . H1121 . 0.950 no
C112 . H1122 . 0.950 no
C112 . H1123 . 0.950 no
O101 . C102 . 1.402(8) yes
O101 . H1011 . 0.833 no
C102 . H1021 . 0.950 no
C102 . H1022 . 0.950 no
C102 . H1023 . 0.950 no
C122 . H1221 . 0.950 no
C122 . H1222 . 0.950 no
C122 . H1223 . 0.950 no
C55 . C54 . 1.396(9) yes
C55 . C56 . 1.401(9) yes
C55 . H551 . 0.925 no
C54 . C53 . 1.385(10) yes
C54 . H541 . 0.943 no
C51 . C52 . 1.398(9) yes
C51 . C56 . 1.426(9) yes
C51 . O51 . 1.348(9) yes
C53 . C52 . 1.407(9) yes
C53 . H531 . 0.933 no
C52 . O52 . 1.353(10) yes
C56 . H561 . 0.950 no
O52 . H522 . 0.850 no
O131 . C132 . 1.355(8) yes
O131 . H1 . 0.850 no
C132 . H1321 . 0.950 no
C132 . H1322 . 0.950 no
C132 . H1323 . 0.950 no
O51 . H511 . 0.850 no
O56 . H562 . 0.850 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
C2 . N1 . C6 . 120.6(7) yes
C2 . N1 . C40 . 120.2(6) yes
C6 . N1 . C40 . 119.0(6) yes
N1 . C2 . C3 . 122.3(7) yes
N1 . C2 . H21 . 117.0 no
C3 . C2 . H21 . 120.7 no
C2 . C3 . C4 . 119.1(7) yes
C2 . C3 . H31 . 120.4 no
C4 . C3 . H31 . 120.5 no
C3 . C4 . C5 . 116.8(6) yes
C3 . C4 . C10 . 122.3(6) yes
C5 . C4 . C10 . 120.9(6) yes
C4 . C5 . C6 . 121.0(7) yes
C4 . C5 . H51 . 119.0 no
C6 . C5 . H51 . 120.1 no
C5 . C6 . N1 . 119.9(7) yes
C5 . C6 . H61 . 120.9 no
N1 . C6 . H61 . 119.2 no
C8 . N7 . C12 . 120.9(6) yes
C8 . N7 . C13 . 119.0(6) yes
C12 . N7 . C13 . 119.8(6) yes
N7 . C8 . C9 . 118.0(7) yes
N7 . C8 . H81 . 121.6 no
C9 . C8 . H81 . 120.5 no
C8 . C9 . C10 . 122.8(7) yes
C8 . C9 . H91 . 116.7 no
C10 . C9 . H91 . 120.4 no
C4 . C10 . C9 . 122.3(6) yes
C4 . C10 . C11 . 121.4(6) yes
C9 . C10 . C11 . 116.2(7) yes
C10 . C11 . C12 . 121.4(7) yes
C10 . C11 . H111 . 120.5 no
C12 . C11 . H111 . 117.9 no
N7 . C12 . C11 . 120.1(7) yes
N7 . C12 . H121 . 119.0 no
C11 . C12 . H121 . 120.9 no
N7 . C13 . C14 . 108.0(5) yes
N7 . C13 . H131 . 110.5 no
C14 . C13 . H131 . 109.9 no
N7 . C13 . H132 . 109.0 no
C14 . C13 . H132 . 110.1 no
H131 . C13 . H132 . 109.4 no
C13 . C14 . C15 . 121.0(6) yes
C13 . C14 . C19 . 118.3(6) yes
C15 . C14 . C19 . 120.6(7) yes
C14 . C15 . C16 . 119.5(7) yes
C14 . C15 . H151 . 120.6 no
C16 . C15 . H151 . 119.9 no
C15 . C16 . C17 . 121.2(7) yes
C15 . C16 . H161 . 119.0 no
C17 . C16 . H161 . 119.8 no
C16 . C17 . C18 . 117.6(6) yes
C16 . C17 . C20 . 121.3(6) yes
C18 . C17 . C20 . 121.1(7) yes
C17 . C18 . C19 . 120.5(7) yes
C17 . C18 . H181 . 119.5 no
C19 . C18 . H181 . 120.0 no
C14 . C19 . C18 . 120.3(7) yes
C14 . C19 . H191 . 120.0 no
C18 . C19 . H191 . 119.7 no
C17 . C20 . N21 . 108.2(5) yes
C17 . C20 . H201 . 110.9 no
N21 . C20 . H201 . 107.6 no
C17 . C20 . H202 . 110.1 no
N21 . C20 . H202 . 111.4 no
H201 . C20 . H202 . 108.6 no
C20 . N21 . C22 . 119.1(6) yes
C20 . N21 . C26 . 118.6(6) yes
C22 . N21 . C26 . 122.0(6) yes
N21 . C22 . C23 . 119.9(6) yes
N21 . C22 . H221 . 119.4 no
C23 . C22 . H221 . 120.7 no
C22 . C23 . C24 . 119.8(7) yes
C22 . C23 . H231 . 119.5 no
C24 . C23 . H231 . 120.6 no
C23 . C24 . C25 . 118.8(6) yes
C23 . C24 . C30 . 120.8(6) yes
C25 . C24 . C30 . 120.2(6) yes
C24 . C25 . C26 . 120.8(7) yes
C24 . C25 . H251 . 119.8 no
C26 . C25 . H251 . 119.4 no
C25 . C26 . N21 . 118.6(7) yes
C25 . C26 . H261 . 122.5 no
N21 . C26 . H261 . 118.9 no
C28 . N27 . C32 . 121.3(6) yes
C28 . N27 . C33 . 120.3(6) yes
C32 . N27 . C33 . 118.3(6) yes
N27 . C28 . C29 . 120.1(7) yes
N27 . C28 . H281 . 120.5 no
C29 . C28 . H281 . 119.4 no
C28 . C29 . C30 . 119.1(7) yes
C28 . C29 . H291 . 120.6 no
C30 . C29 . H291 . 120.3 no
C24 . C30 . C29 . 121.2(6) yes
C24 . C30 . C31 . 119.1(6) yes
C29 . C30 . C31 . 119.5(6) yes
C30 . C31 . C32 . 117.4(6) yes
C30 . C31 . H311 . 120.8 no
C32 . C31 . H311 . 121.7 no
C31 . C32 . N27 . 122.4(6) yes
C31 . C32 . H321 . 119.0 no
N27 . C32 . H321 . 118.6 no
N27 . C33 . C34 . 109.5(6) yes
N27 . C33 . H331 . 109.1 no
C34 . C33 . H331 . 109.6 no
N27 . C33 . H332 . 108.8 no
C34 . C33 . H332 . 111.1 no
H331 . C33 . H332 . 108.8 no
C33 . C34 . C35 . 121.5(6) yes
C33 . C34 . C39 . 120.7(7) yes
C35 . C34 . C39 . 117.4(7) yes
C34 . C35 . C36 . 121.3(6) yes
C34 . C35 . H351 . 119.6 no
C36 . C35 . H351 . 119.1 no
C35 . C36 . C37 . 119.8(7) yes
C35 . C36 . H361 . 119.9 no
C37 . C36 . H361 . 120.3 no
C36 . C37 . C38 . 120.6(7) yes
C36 . C37 . C40 . 117.4(6) yes
C38 . C37 . C40 . 121.4(6) yes
C37 . C38 . C39 . 119.8(7) yes
C37 . C38 . H381 . 119.7 no
C39 . C38 . H381 . 120.5 no
C34 . C39 . C38 . 121.1(7) yes
C34 . C39 . H391 . 119.4 no
C38 . C39 . H391 . 119.5 no
C37 . C40 . N1 . 108.6(5) yes
C37 . C40 . H401 . 110.3 no
N1 . C40 . H401 . 107.9 no
C37 . C40 . H402 . 109.9 no
N1 . C40 . H402 . 110.5 no
H401 . C40 . H402 . 109.7 no
C122 . O121 . H1211 . 111.0 no
C112 . O111 . H1111 . 107.3 no
O111 . C112 . H1121 . 109.8 no
O111 . C112 . H1122 . 106.0 no
H1121 . C112 . H1122 . 109.5 no
O111 . C112 . H1123 . 112.6 no
H1121 . C112 . H1123 . 109.5 no
H1122 . C112 . H1123 . 109.5 no
C102 . O101 . H1011 . 106.7 no
O101 . C102 . H1021 . 112.4 no
O101 . C102 . H1022 . 104.4 no
H1021 . C102 . H1022 . 109.5 no
O101 . C102 . H1023 . 111.5 no
H1021 . C102 . H1023 . 109.5 no
H1022 . C102 . H1023 . 109.5 no
O121 . C122 . H1221 . 109.6 no
O121 . C122 . H1222 . 107.4 no
H1221 . C122 . H1222 . 109.5 no
O121 . C122 . H1223 . 111.4 no
H1221 . C122 . H1223 . 109.5 no
H1222 . C122 . H1223 . 109.5 no
C54 . C55 . C56 . 120.8(7) yes
C54 . C55 . H551 . 121.2 no
C56 . C55 . H551 . 118.0 no
C55 . C54 . C53 . 120.6(7) yes
C55 . C54 . H541 . 119.1 no
C53 . C54 . H541 . 120.3 no
C52 . C51 . C56 . 119.5(6) yes
C52 . C51 . O51 . 118.1(7) yes
C56 . C51 . O51 . 122.3(7) yes
C54 . C53 . C52 . 119.6(7) yes
C54 . C53 . H531 . 119.7 no
C52 . C53 . H531 . 120.6 no
C53 . C52 . C51 . 120.6(6) yes
C53 . C52 . O52 . 120.0(7) yes
C51 . C52 . O52 . 119.4(7) yes
C51 . C56 . C55 . 118.8(6) yes
C51 . C56 . H561 . 119.3 no
C55 . C56 . H561 . 121.9 no
C52 . O52 . H522 . 119.7 no
C132 . O131 . H1 . 113.8 no
O131 . C132 . H1321 . 110.3 no
O131 . C132 . H1322 . 110.3 no
H1321 . C132 . H1322 . 109.5 no
O131 . C132 . H1323 . 107.8 no
H1321 . C132 . H1323 . 109.5 no
H1322 . C132 . H1323 . 109.5 no
C51 . O51 . H511 . 119.9 no
C56 . O56 . H562 . 120.5 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
C6 . H61 . O111 . 140 0.95 2.29 3.079(14) yes
C12 . H121 . O121 . 129 0.92 2.56 3.218(14) yes
C12 . H121 . O101 1_556 139 0.92 2.46 3.209(14) yes
C22 . H221 . O131 1_565 131 0.94 2.31 3.013(14) yes
C28 . H281 . O121 1_554 145 0.92 2.39 3.195(14) yes
C102 . H1022 . O51 . 153 0.95 1.89 2.764(14) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 28/10/18 at 15:19:01
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) H   ( 332,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) H   ( 402,X'S) 
RIDE O   ( 121,X'S) H   (1211,X'S) 
RIDE O   ( 111,X'S) H   (1111,X'S) 
RIDE C   ( 112,X'S) H   (1121,X'S) H   (1122,X'S) H   (1123,X'S) 
RIDE O   ( 101,X'S) H   (1011,X'S) 
RIDE C   ( 102,X'S) H   (1021,X'S) H   (1022,X'S) H   (1023,X'S) 
RIDE C   ( 122,X'S) H   (1221,X'S) H   (1222,X'S) H   (1223,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE O   (  52,X'S) H   ( 522,X'S) 
RIDE O   ( 131,X'S) H   (   1,X'S) 
RIDE C   ( 132,X'S) H   (1321,X'S) H   (1322,X'S) H   (1323,X'S) 
RIDE O   (  51,X'S) H   ( 511,X'S) 
RIDE O   (  56,X'S) H   ( 562,X'S) 
END
;

_iucr_refine_instructions_details_restraints 
;                                                                             
#
# Punched on 28/10/18 at 15:19:01
#
#LIST     16                                                                    
REM 
REM CATECHOL 
REM 
PLANAR O(51) O(52) C(51) C(52) C(53) C(54) C(55) C(56) O(56) 
DIST 1.36, 0.01 = O(51) TO C(51), O(52) TO C(52) 
CONT O(56) TO C(56) 
DIST 1.40, 0.01 = C(51) TO C(52), C(52) TO C(53) 
CONT C(53) TO C(54), C(54) TO C(55) 
CONT C(55) TO C(56), C(56) TO C(51) 
ANGL 120, 1 = C(51) TO C(52) TO C(53) 
CONT C(52) TO C(53) TO C(54) 
CONT C(53) TO C(54) TO C(55) 
CONT C(54) TO C(55) TO C(56) 
CONT C(55) TO C(56) TO C(51) 
CONT C(56) TO C(51) TO C(52) 
CONT O(51) TO C(51) TO C(52) 
CONT O(51) TO C(51) TO C(56) 
CONT O(52) TO C(52) TO C(51) 
CONT O(52) TO C(52) TO C(53) 
CONT O(56) TO C(56) TO C(51) 
CONT O(56) TO C(56) TO C(55) 
REM 
REM METHANOLS 
REM 
DIST 1.43, 0.01 = O(101) TO C(102), O(111) TO C(112) 
CONT O(121) TO C(122), O(131) TO C(132) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00100 = C(55) TO C(54) 
VIBR .0, 0.00100 = C(55) TO C(56) 
VIBR .0, 0.00200 = C(56) TO C(54) 
VIBR .0, 0.00100 = C(54) TO C(53) 
VIBR .0, 0.00200 = C(53) TO C(55) 
VIBR .0, 0.00100 = C(51) TO C(52) 
VIBR .0, 0.00100 = C(51) TO C(56) 
VIBR .0, 0.00100 = C(51) TO O(51) 
VIBR .0, 0.00200 = C(56) TO C(52) 
VIBR .0, 0.00200 = O(51) TO C(52) 
VIBR .0, 0.00200 = O(51) TO C(56) 
VIBR .0, 0.00100 = C(53) TO C(52) 
VIBR .0, 0.00200 = C(52) TO C(54) 
VIBR .0, 0.00100 = C(52) TO O(52) 
VIBR .0, 0.00200 = C(51) TO C(53) 
VIBR .0, 0.00200 = O(52) TO C(53) 
VIBR .0, 0.00200 = O(52) TO C(51) 
VIBR .0, 0.00100 = C(56) TO O(56) 
VIBR .0, 0.00200 = C(55) TO C(51) 
VIBR .0, 0.00200 = O(56) TO C(51) 
VIBR .0, 0.00200 = O(56) TO C(55) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.01000 = C(55) TO C(54) 
U(IJ) .0, 0.01000 = C(55) TO C(56) 
U(IJ) .0, 0.01000 = C(54) TO C(53) 
U(IJ) .0, 0.01000 = C(51) TO C(52) 
U(IJ) .0, 0.01000 = C(51) TO C(56) 
U(IJ) .0, 0.02000 = C(51) TO O(51) 
U(IJ) .0, 0.01000 = C(53) TO C(52) 
U(IJ) .0, 0.02000 = C(52) TO O(52) 
U(IJ) .0, 0.02000 = C(56) TO O(56) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 -3 2 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol, diethyl ether'
