# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global

_journal_coden_Cambridge         1350
loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
'Catherine E Housecroft'
;
? # Address for author 1
;
;
? # Footnote for author 1
;
'Edwin Constable'
;
? # Address 2
;
;
? # Footnote 2
;
'Markus Neuburger' '' ''
'Silvia Schaffner' '' ''
'Guoqi Zhang.' '' ''

_publ_contact_author_name        'Catherine E Housecroft'
_publ_contact_author_email       CATHERINE.HOUSECROFT@UNIBAS.CH

_publ_section_title              
;
Phase-separated hydrogen-bonded chloride
ion-water-oxonium ion sheets and protonated
4'-(4-bromophenyl)-2,2':6',2"-terpyridine stacks, and condensation
products of 2-acetylpyridine and benzaldehydes revisited
;
_journal_coden_ASTM              ?
_journal_coeditor_code           ?
_journal_coeditor_name           ?
_journal_coeditor_notes          ?
_journal_date_accepted           ?
_journal_date_from_coeditor      ?
_journal_date_printers_final     ?
_journal_date_printers_first     ?
_journal_date_proofs_in          ?
_journal_date_proofs_out         ?

# PROCESSING SUMMARY (IUCr Office Use Only):
_journal_date_recd_electronic    ?
_journal_date_to_coeditor        ?
_journal_issue                   ?
_journal_name_full               ?
_journal_page_first              ?
_journal_page_last               ?
_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?
_journal_techeditor_code         ?
_journal_techeditor_notes        ?
_journal_volume                  ?
_journal_year                    ?
_publ_contact_author_address     
;
Chemical Crystallography Laboratory,
Department of Chemistry,
University of Nowhere,
Nowhere, NO1 4T, UK.
;
_publ_contact_author_fax         '+44 1865 000000'

_publ_contact_author_phone       '+44 1865 000000'

# Check this file using the IUCr facility at:
# http://checkcif.iucr.org/

# The content below is held in the file 'script/refcif.dat'. This is a text
# file which you may edit to reflect local conditions.
# Items which need looking at are represented by a '?'.
# Items for which there are choices are prefixed with 'choose from'.

_publ_contact_letter             
;
Please consider this CIF submission for
publication as a Short Format Paper in Acta
Crystallographica E. The figures will be
sent by e-mail.
;
_publ_requested_category         EO # choose from: FI FM FO CI CM CO AD
_publ_requested_coeditor_name    'Prof William Clegg'
_publ_requested_journal          'Section E'

# Attachment 'Protonated1.cif'

data_gq4_223k
_database_code_depnum_ccdc_archive 'CCDC 708557'
_audit_creation_date             08-10-13
_audit_creation_method           CRYSTALS_ver_12.84

_oxford_structure_analysis_title 'gq4_223k_0m in P2(1)/n'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   7.3916(2)
_cell_length_b                   28.4550(10)
_cell_length_c                   12.1415(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.905(2)
_cell_angle_gamma                90
_cell_volume                     2547.77(13)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1484 0.1585 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'
Br -0.2901 2.4595 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'

_cell_formula_units_Z            4

# Given Formula = C21 H25 Br1 Cl3 N3 O4
# Dc = 1.49 Fooo = 1160.00 Mu = 19.59 M = 569.71
# Found Formula = C21 H25 Br1 Cl3 N3 O4
# Dc = 1.49 FOOO = 1160.00 Mu = 19.59 M = 569.71

_chemical_formula_sum            'C21 H25 Br1 Cl3 N3 O4'
_chemical_formula_moiety         'C21 H16 Br N3, H3 O, 3(H2 O), 3(Cl)'
_chemical_compound_source        ?
_chemical_formula_weight         569.71

_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    223

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.04
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_max          0.19

_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             1160
_exptl_absorpt_coefficient_mu    1.959

# Sheldrick geometric approximatio 0.87 0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.92
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'USER DEFINED STRUCTURE SOLUTION'
_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      223
_diffrn_reflns_number            31822
_reflns_number_total             7235
_diffrn_reflns_av_R_equivalents  0.046
# Number of reflections with Friedels Law is 7235
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 7326

_diffrn_reflns_theta_min         1.827
_diffrn_reflns_theta_max         29.865
_diffrn_measured_fraction_theta_max 0.985

_diffrn_reflns_theta_full        29.268
_diffrn_measured_fraction_theta_full 0.996

_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              39
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.39
_refine_diff_density_max         0.58

_refine_ls_number_reflns         3870
_refine_ls_number_restraints     0
_refine_ls_number_parameters     289

#_refine_ls_R_factor_ref 0.0289
_refine_ls_wR_factor_ref         0.0311
_refine_ls_goodness_of_fit_ref   1.0614

#_reflns_number_all 7215
_refine_ls_R_factor_all          0.0640
_refine_ls_wR_factor_all         0.0636

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.0σ(I)
_reflns_number_gt                3870
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_gt          0.0311

_refine_ls_shift/su_max          0.001463

# 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 F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
0.540 0.562 0.340 0.731E-01
;

_publ_section_abstract           
# Text of the abstract
# (a) The Abstract must be self-contained and comprehensible
# without the rest of the paper. This means no references
# to atom names or to compound numbers; compounds must be
# identified as the title compound, or by name or by some other
# means such as derivatives of each other (e.g. "the
# corresponding ketone").
# (b) The chemical formula of "the title compound" must be given.
# (c) Any crystallographic molecular symmetry should be
# mentioned, and also the presence of more than one molecule
# in the asymmetric unit (i.e. anything other than Z'=1).
;
?
;
_publ_section_comment            
# Text of the paper
# Note that atoms are referenced as N2, not N(2) or N~2~
# If text containing () occur within (), the outer ones should be []
# Figures should be referenced as Fih.
;
?
;
_publ_section_acknowledgements   # Acknowledgments
;
?
;
_publ_section_figure_captions    
# Captions to figures - Start each caption on a new line after a blank line
;
Fig. 1.
The title compound with displacement ellipsoids drawn at the 50%
probability level. H atoms are shown as spheres of
arbitary radius.

;

_publ_section_exptl_refinement   
# Some potentially useful phrases are donated by Bill Clegg:
;
In the absence of significant anomalous scattering, Friedel pairs were
merged.

The absolute configuration was arbitrarily assigned.

The relatively large ratio of minimum to maximum corrections applied
in the multiscan process (1:nnn) reflect changes in the illuminated
volume of the crystal.

Changes in illuminated volume were kept to a minimum, and were
taken into account (Görbitz, 1999) by the multi-scan inter-frame
scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).

Görbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.

The H atoms were all located in a difference map, but those
attached to carbon atoms 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--0.98,
N---H in the range 0.86--0.89
N---H to 0.86
O---H = 0.82
Å)
and
Uiso(H) (in the range 1.2-1.5 times Ueq of the parent atom),
after which the positions were refined with riding constraints.

;

_publ_section_exptl_prep         
# Brief details or a reference. Include solvent if known
;
?
;

# End of 'script/refcif.dat'

# Insert your own references if required - in alphabetical order
_publ_section_references         
;
User-defined structure solution reference

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R.,
Munksgaard, Copenhagen, 291-294.

Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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 -0.51601(3) 0.400721(10) 0.53535(2) 0.0388 1.0000 Uani . . . . . .
N1 N 0.4680(2) 0.60720(6) 0.15424(16) 0.0297 1.0000 Uani . . . . . .
N2 N 0.4071(2) 0.51500(6) 0.17570(15) 0.0260 1.0000 Uani . . . . . .
N3 N 0.6693(2) 0.46163(6) 0.10640(15) 0.0269 1.0000 Uani . . . . . .
C1 C 0.5072(3) 0.65146(9) 0.1284(2) 0.0384 1.0000 Uani . . . . . .
C2 C 0.3840(4) 0.68666(9) 0.1414(2) 0.0433 1.0000 Uani . . . . . .
C3 C 0.2203(4) 0.67497(9) 0.1824(2) 0.0414 1.0000 Uani . . . . . .
C4 C 0.1823(3) 0.62889(8) 0.2089(2) 0.0354 1.0000 Uani . . . . . .
C5 C 0.3100(3) 0.59435(8) 0.19389(17) 0.0268 1.0000 Uani . . . . . .
C6 C 0.2852(3) 0.54379(8) 0.21659(18) 0.0259 1.0000 Uani . . . . . .
C7 C 0.1446(3) 0.52803(8) 0.27736(18) 0.0275 1.0000 Uani . . . . . .
C8 C 0.1229(3) 0.47976(8) 0.29413(17) 0.0256 1.0000 Uani . . . . . .
C9 C 0.2470(3) 0.44972(8) 0.24898(18) 0.0268 1.0000 Uani . . . . . .
C10 C 0.3870(3) 0.46881(8) 0.19266(17) 0.0250 1.0000 Uani . . . . . .
C11 C 0.5321(3) 0.43890(8) 0.15126(17) 0.0265 1.0000 Uani . . . . . .
C12 C 0.5425(3) 0.39075(8) 0.1601(2) 0.0372 1.0000 Uani . . . . . .
C13 C 0.6924(4) 0.36733(9) 0.1256(2) 0.0422 1.0000 Uani . . . . . .
C14 C 0.8322(3) 0.39211(9) 0.0822(2) 0.0374 1.0000 Uani . . . . . .
C15 C 0.8157(3) 0.43983(9) 0.07227(19) 0.0315 1.0000 Uani . . . . . .
C16 C -0.0273(3) 0.46166(8) 0.35652(17) 0.0261 1.0000 Uani . . . . . .
C17 C -0.0150(3) 0.41820(9) 0.4095(2) 0.0341 1.0000 Uani . . . . . .
C18 C -0.1577(3) 0.40054(9) 0.4649(2) 0.0347 1.0000 Uani . . . . . .
C19 C -0.3163(3) 0.42624(8) 0.46571(18) 0.0300 1.0000 Uani . . . . . .
C20 C -0.3317(3) 0.46984(8) 0.41610(17) 0.0292 1.0000 Uani . . . . . .
C21 C -0.1874(3) 0.48745(8) 0.36191(18) 0.0291 1.0000 Uani . . . . . .
Cl1 Cl 0.80577(7) 0.56139(2) 0.07610(5) 0.0372 1.0000 Uani . . . . . .
Cl2 Cl 0.17467(10) 0.31452(3) 0.23040(7) 0.0554 1.0000 Uani . . . . . .
Cl3 Cl 0.17192(9) 0.32403(3) 0.64808(6) 0.0524 1.0000 Uani . . . . . .
O1 O 0.3536(3) 0.28056(7) 0.45029(18) 0.0540 1.0000 Uani . . . . . .
O2 O 0.6880(3) 0.28693(9) 0.4394(2) 0.0680 1.0000 Uani . . . . . .
O3 O 0.7994(3) 0.26925(8) 0.25303(17) 0.0536 1.0000 Uani . . . . . .
O4 O 0.8989(3) 0.24229(9) 0.57245(18) 0.0663 1.0000 Uani . . . . . .
H1 H 0.5459 0.5859 0.1440 0.0368 1.0000 Uiso R . . . . .
H2 H 0.6630 0.4911 0.0998 0.0319 1.0000 Uiso R . . . . .
H3 H 0.3108 0.2925 0.5049 0.0810 1.0000 Uiso R . . . . .
H4 H 0.3023 0.2933 0.3972 0.0813 1.0000 Uiso R . . . . .
H5 H 0.7189 0.2808 0.3764 0.1024 1.0000 Uiso R . . . . .
H6 H 0.5858 0.2754 0.4420 0.1022 1.0000 Uiso R . . . . .
H7 H 0.8949 0.2829 0.2427 0.0812 1.0000 Uiso R . . . . .
H8 H 0.7959 0.2441 0.2187 0.0809 1.0000 Uiso R . . . . .
H9 H 0.9730 0.2599 0.6066 0.0992 1.0000 Uiso R . . . . .
H10 H 0.8308 0.2630 0.5452 0.0996 1.0000 Uiso R . . . . .
H11 H 0.6178 0.6575 0.1012 0.0457 1.0000 Uiso R . . . . .
H12 H 0.8420 0.2286 0.6191 0.0992 1.0000 Uiso R . . . . .
H21 H 0.4136 0.7174 0.1227 0.0519 1.0000 Uiso R . . . . .
H31 H 0.1325 0.6982 0.1924 0.0501 1.0000 Uiso R . . . . .
H41 H 0.0721 0.6210 0.2345 0.0430 1.0000 Uiso R . . . . .
H71 H 0.0664 0.5494 0.3077 0.0338 1.0000 Uiso R . . . . .
H91 H 0.2361 0.4168 0.2567 0.0324 1.0000 Uiso R . . . . .
H121 H 0.4500 0.3738 0.1899 0.0462 1.0000 Uiso R . . . . .
H131 H 0.6999 0.3349 0.1323 0.0510 1.0000 Uiso R . . . . .
H141 H 0.9331 0.3770 0.0605 0.0459 1.0000 Uiso R . . . . .
H151 H 0.9056 0.4574 0.0426 0.0378 1.0000 Uiso R . . . . .
H171 H 0.0911 0.4004 0.4083 0.0413 1.0000 Uiso R . . . . .
H181 H -0.1480 0.3711 0.5002 0.0415 1.0000 Uiso R . . . . .
H201 H -0.4378 0.4878 0.4187 0.0355 1.0000 Uiso R . . . . .
H211 H -0.1992 0.5167 0.3287 0.0348 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1941(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
Br1 . C19 . 1.895(2) yes
N1 . C1 . 1.335(3) yes
N1 . C5 . 1.344(3) yes
N1 . H1 . 0.850 no
N2 . C6 . 1.338(3) yes
N2 . C10 . 1.340(3) yes
N3 . C11 . 1.349(3) yes
N3 . C15 . 1.337(3) yes
N3 . H2 . 0.843 no
C1 . C2 . 1.370(4) yes
C1 . H11 . 0.918 no
C2 . C3 . 1.380(4) yes
C2 . H21 . 0.934 no
C3 . C4 . 1.384(3) yes
C3 . H31 . 0.939 no
C4 . C5 . 1.383(3) yes
C4 . H41 . 0.919 no
C5 . C6 . 1.479(3) yes
C6 . C7 . 1.390(3) yes
C7 . C8 . 1.399(3) yes
C7 . H71 . 0.931 no
C8 . C9 . 1.393(3) yes
C8 . C16 . 1.479(3) yes
C9 . C10 . 1.389(3) yes
C9 . H91 . 0.945 no
C10 . C11 . 1.483(3) yes
C11 . C12 . 1.376(3) yes
C12 . C13 . 1.382(3) yes
C12 . H121 . 0.930 no
C13 . C14 . 1.384(4) yes
C13 . H131 . 0.927 no
C14 . C15 . 1.368(4) yes
C14 . H141 . 0.916 no
C15 . H151 . 0.924 no
C16 . C17 . 1.394(3) yes
C16 . C21 . 1.398(3) yes
C17 . C18 . 1.384(3) yes
C17 . H171 . 0.935 no
C18 . C19 . 1.382(3) yes
C18 . H181 . 0.942 no
C19 . C20 . 1.381(3) yes
C20 . C21 . 1.385(3) yes
C20 . H201 . 0.939 no
C21 . H211 . 0.926 no
O1 . H3 . 0.827 no
O1 . H4 . 0.811 no
O2 . H5 . 0.831 no
O2 . H6 . 0.827 no
O3 . H7 . 0.823 no
O3 . H8 . 0.828 no
O4 . H9 . 0.833 no
O4 . H10 . 0.829 no
O4 . H12 . 0.826 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
C1 . N1 . C5 . 123.3(2) yes
C1 . N1 . H1 . 118.4 no
C5 . N1 . H1 . 118.2 no
C6 . N2 . C10 . 117.36(18) yes
C11 . N3 . C15 . 123.33(19) yes
C11 . N3 . H2 . 118.5 no
C15 . N3 . H2 . 118.2 no
N1 . C1 . C2 . 120.4(2) yes
N1 . C1 . H11 . 118.2 no
C2 . C1 . H11 . 121.4 no
C1 . C2 . C3 . 118.1(2) yes
C1 . C2 . H21 . 119.2 no
C3 . C2 . H21 . 122.6 no
C2 . C3 . C4 . 120.6(2) yes
C2 . C3 . H31 . 120.5 no
C4 . C3 . H31 . 118.9 no
C3 . C4 . C5 . 119.5(2) yes
C3 . C4 . H41 . 120.6 no
C5 . C4 . H41 . 120.0 no
C4 . C5 . N1 . 118.1(2) yes
C4 . C5 . C6 . 124.93(19) yes
N1 . C5 . C6 . 116.95(19) yes
C5 . C6 . N2 . 115.58(18) yes
C5 . C6 . C7 . 121.30(19) yes
N2 . C6 . C7 . 123.1(2) yes
C6 . C7 . C8 . 119.41(19) yes
C6 . C7 . H71 . 120.4 no
C8 . C7 . H71 . 120.1 no
C7 . C8 . C9 . 117.39(18) yes
C7 . C8 . C16 . 120.91(19) yes
C9 . C8 . C16 . 121.7(2) yes
C8 . C9 . C10 . 119.1(2) yes
C8 . C9 . H91 . 120.4 no
C10 . C9 . H91 . 120.5 no
C9 . C10 . N2 . 123.56(19) yes
C9 . C10 . C11 . 121.49(19) yes
N2 . C10 . C11 . 114.88(18) yes
C10 . C11 . N3 . 116.27(19) yes
C10 . C11 . C12 . 125.66(19) yes
N3 . C11 . C12 . 117.98(19) yes
C11 . C12 . C13 . 119.9(2) yes
C11 . C12 . H121 . 120.5 no
C13 . C12 . H121 . 119.6 no
C12 . C13 . C14 . 120.3(2) yes
C12 . C13 . H131 . 119.9 no
C14 . C13 . H131 . 119.8 no
C13 . C14 . C15 . 118.4(2) yes
C13 . C14 . H141 . 120.9 no
C15 . C14 . H141 . 120.7 no
C14 . C15 . N3 . 120.1(2) yes
C14 . C15 . H151 . 120.6 no
N3 . C15 . H151 . 119.2 no
C8 . C16 . C17 . 121.20(19) yes
C8 . C16 . C21 . 120.6(2) yes
C17 . C16 . C21 . 118.21(19) yes
C16 . C17 . C18 . 121.3(2) yes
C16 . C17 . H171 . 120.2 no
C18 . C17 . H171 . 118.6 no
C17 . C18 . C19 . 119.1(2) yes
C17 . C18 . H181 . 120.5 no
C19 . C18 . H181 . 120.4 no
Br1 . C19 . C18 . 119.17(17) yes
Br1 . C19 . C20 . 119.70(16) yes
C18 . C19 . C20 . 121.1(2) yes
C19 . C20 . C21 . 119.3(2) yes
C19 . C20 . H201 . 121.3 no
C21 . C20 . H201 . 119.4 no
C16 . C21 . C20 . 121.0(2) yes
C16 . C21 . H211 . 120.4 no
C20 . C21 . H211 . 118.6 no
H3 . O1 . H4 . 105.7 no
H5 . O2 . H6 . 105.1 no
H7 . O3 . H8 . 109.2 no
H9 . O4 . H10 . 97.5 no
H9 . O4 . H12 . 107.0 no
H10 . O4 . H12 . 106.6 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
O2 . H5 . O3 . 175 0.83 1.68 2.511(2) yes
O2 . H6 . O1 . 152 0.83 1.73 2.491(2) yes
O4 . H10 . O2 . 153 0.83 1.74 2.512(2) yes

# Attachment 'compound_3.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 708558'

_publ_section_exptl_refinement   
# Some potentially useful phrases are donated by Bill Clegg:
;
In the absence of significant anomalous scattering, Friedel pairs were
merged.

The absolute configuration was arbitrarily assigned.

The relatively large ratio of minimum to maximum corrections applied
in the multiscan process (1:nnn) reflect changes in the illuminated
volume of the crystal.

Changes in illuminated volume were kept to a minimum, and were
taken into account (Görbitz, 1999) by the multi-scan inter-frame
scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).

Görbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.

The H atoms were all located in a difference map, but those
attached to carbon atoms 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--0.98,
N---H in the range 0.86--0.89
N---H to 0.86
O---H = 0.82
Å)
and
Uiso(H) (in the range 1.2-1.5 times Ueq of the parent atom),
after which the positions were refined with riding constraints.

;

_publ_section_exptl_prep         
# Brief details or a reference. Include solvent if known
;
?
;

# Hand-made tables can be put in the cif. The number of columns
# is set in the loop header.
# The contants of each column can either be a piece of text
# without any spaces (eg a number) or other text enclosed in " "
# Remove the leading # in the following example

#geom_extra_table_head_A
#;
#Table 2.
#Molecular parameters deviating most from MOGUL averages
#;
#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
#_geom_extra_tableA_col_4
#
#Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d"
#N5-C6-C4 129 124 "7 (\%)"
#C3-O10-C2 105 109 "2 (\%)"
#C6-O7 1.25 1.22 ".02 (\%A)"
#
# End of 'script/refcif-b.dat'
#end of refcif
_cell_length_a                   16.8561(4)
_cell_length_b                   53.1999(16)
_cell_length_c                   15.4900(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     13890.5(7)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'F d d 2 '
_symmetry_space_group_name_Hall  'F 2 -2d '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,y+1/2,z+1/2
x+1/2,y,z+1/2
x+1/2,y+1/2,z
-x+1/4,y+1/4,z+1/4
-x+1/4,y+3/4,z+3/4
-x+3/4,y+1/4,z+3/4
-x+3/4,y+3/4,z+1/4
x+1/4,-y+1/4,z+1/4
x+1/4,-y+3/4,z+3/4
x+3/4,-y+1/4,z+3/4
x+3/4,-y+3/4,z+1/4
-x+1/2,-y,z+1/2
-x+1/2,-y+1/2,z+1
-x+1,-y,z+1
-x+1,-y+1/2,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 0.0033 0.0016 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 0.0061 0.0033 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'
Br -0.2901 2.4595 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'
Cl 0.1484 0.1585 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'
O 0.0106 0.0060 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            16

# Given Formula = C36 H28 Br2 Cl3 N3 O3
# Dc = 1.56 Fooo = 6560.00 Mu = 26.06 M = 816.80
# Found Formula = C36 H28 Br2 Cl3 N3 O3
# Dc = 1.56 FOOO = 6560.00 Mu = 26.06 M = 816.80

_chemical_formula_sum            'C36 H28 Br2 Cl3 N3 O3'
_chemical_formula_moiety         'C35 H27 Br2 N3 O3, C H Cl3'
_chemical_compound_source        ?
_chemical_formula_weight         816.80

_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    223

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.06
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_max          0.34

_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             6560
_exptl_absorpt_coefficient_mu    2.606

# Sheldrick geometric approximatio 0.64 0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  0.86
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      223
_diffrn_reflns_number            24246
_reflns_number_total             9756
_diffrn_reflns_av_R_equivalents  0.024
# Number of reflections with Friedels Law is 23695
# Number of reflections without Friedels Law is 9756
# Theoretical number of reflections is about 5082

_diffrn_reflns_theta_min         1.531
_diffrn_reflns_theta_max         30.038
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        30.038
_diffrn_measured_fraction_theta_full 0.996

_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -74
_diffrn_reflns_limit_k_max       74
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              0
_reflns_limit_h_max              23
_reflns_limit_k_min              0
_reflns_limit_k_max              74
_reflns_limit_l_min              -21
_reflns_limit_l_max              21

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.71
_refine_diff_density_max         0.86

# 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>3.0\s(I)
_refine_ls_number_reflns         6976
_refine_ls_number_restraints     55
_refine_ls_number_parameters     452
_oxford_refine_ls_R_factor_ref   0.0300
_refine_ls_wR_factor_ref         0.0267
_refine_ls_goodness_of_fit_ref   1.0671
_refine_ls_shift/su_max          0.002640

# The values computed from all data
_oxford_reflns_number_all        9725
_refine_ls_R_factor_all          0.0428
_refine_ls_wR_factor_all         0.0308

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                7744
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_gt          0.0278

# The Flack parameter was determined before Friedel pairs were merged
_refine_ls_abs_structure_Flack   0.022(5)
_refine_ls_abs_structure_details 'Flack (1983), 0 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 F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
0.213 -0.941 -0.124 -0.456
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Flack, H. D. (1983). Acta Cryst. A39, 876-881.

Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Br1 Br 0.20063(2) 0.512909(6) 0.33173(5) 0.0604 1.0000 Uani . . . . . . .
Br2 Br 0.38475(2) 0.747844(5) 0.25672(5) 0.0640 1.0000 Uani . . . . . . .
O1 O 0.45814(11) 0.60767(3) -0.03783(11) 0.0399 1.0000 Uani . . . . . . .
O2 O 0.42139(12) 0.55391(3) 0.01074(13) 0.0451 1.0000 Uani . . . . . . .
O3 O 0.46693(10) 0.61827(4) 0.27485(11) 0.0378 1.0000 Uani . . . . . . .
N1 N 0.59902(15) 0.58983(4) -0.06046(15) 0.0450 1.0000 Uani . . . . . . .
N2 N 0.56641(14) 0.54806(5) 0.17034(16) 0.0454 1.0000 Uani . . . . . . .
N3 N 0.26546(12) 0.63528(4) 0.29632(14) 0.0388 1.0000 Uani . . . . . . .
C1 C 0.50257(14) 0.60641(4) 0.03979(14) 0.0314 1.0000 Uani . . . . . . .
C2 C 0.46443(13) 0.58712(4) 0.10344(13) 0.0276 1.0000 Uani . . . . . . .
C3 C 0.37826(13) 0.59454(4) 0.12245(13) 0.0273 1.0000 Uani . . . . . . .
C4 C 0.37096(13) 0.62142(4) 0.16035(14) 0.0268 1.0000 Uani . . . . . . .
C5 C 0.41559(14) 0.64066(4) 0.10225(14) 0.0304 1.0000 Uani . . . . . . .
C6 C 0.50040(13) 0.63257(4) 0.08148(16) 0.0321 1.0000 Uani . . . . . . .
C7 C 0.58733(14) 0.59819(4) 0.01996(15) 0.0332 1.0000 Uani . . . . . . .
C8 C 0.64666(15) 0.59831(5) 0.08130(19) 0.0404 1.0000 Uani . . . . . . .
C9 C 0.72063(18) 0.58873(6) 0.0596(2) 0.0521 1.0000 Uani . . . . . . .
C10 C 0.7324(2) 0.57944(6) -0.0231(2) 0.0598 1.0000 Uani . . . . . . .
C11 C 0.6715(2) 0.58068(6) -0.0792(2) 0.0580 1.0000 Uani . . . . . . .
C12 C 0.46859(14) 0.56100(4) 0.06410(15) 0.0322 1.0000 Uani . . . . . . .
C13 C 0.53523(14) 0.54404(4) 0.09184(16) 0.0342 1.0000 Uani . . . . . . .
C14 C 0.5615(2) 0.52539(5) 0.0368(2) 0.0522 1.0000 Uani . . . . . . .
C15 C 0.6217(2) 0.50964(6) 0.0637(2) 0.0634 1.0000 Uani . . . . . . .
C16 C 0.6541(2) 0.51350(6) 0.1445(2) 0.0620 1.0000 Uani . . . . . . .
C17 C 0.62505(19) 0.53274(7) 0.1955(2) 0.0571 1.0000 Uani . . . . . . .
C18 C 0.33556(14) 0.57516(4) 0.17690(15) 0.0295 1.0000 Uani . . . . . . .
C19 C 0.37288(15) 0.56192(5) 0.24341(17) 0.0379 1.0000 Uani . . . . . . .
C20 C 0.33292(17) 0.54357(5) 0.29020(17) 0.0410 1.0000 Uani . . . . . . .
C21 C 0.25569(16) 0.53838(4) 0.27016(16) 0.0378 1.0000 Uani . . . . . . .
C22 C 0.21623(16) 0.55115(5) 0.20469(18) 0.0422 1.0000 Uani . . . . . . .
C23 C 0.25676(14) 0.56938(5) 0.15927(16) 0.0353 1.0000 Uani . . . . . . .
C24 C 0.39909(12) 0.62275(4) 0.25357(14) 0.0266 1.0000 Uani . . . . . . .
C25 C 0.33964(13) 0.63058(4) 0.32167(15) 0.0285 1.0000 Uani . . . . . . .
C26 C 0.36455(15) 0.63289(5) 0.40648(15) 0.0363 1.0000 Uani . . . . . . .
C27 C 0.30978(18) 0.64132(5) 0.46749(17) 0.0456 1.0000 Uani . . . . . . .
C28 C 0.23415(18) 0.64661(6) 0.44161(19) 0.0488 1.0000 Uani . . . . . . .
C29 C 0.21463(17) 0.64287(6) 0.35586(19) 0.0497 1.0000 Uani . . . . . . .
C30 C 0.41037(15) 0.66712(4) 0.13969(15) 0.0318 1.0000 Uani . . . . . . .
C31 C 0.33655(17) 0.67875(5) 0.14376(18) 0.0415 1.0000 Uani . . . . . . .
C32 C 0.32815(18) 0.70273(5) 0.1778(2) 0.0454 1.0000 Uani . . . . . . .
C33 C 0.39530(18) 0.71512(4) 0.20821(17) 0.0426 1.0000 Uani . . . . . . .
C34 C 0.46850(17) 0.70418(5) 0.20449(18) 0.0427 1.0000 Uani . . . . . . .
C35 C 0.47564(16) 0.68011(5) 0.16994(17) 0.0382 1.0000 Uani . . . . . . .
C41 C 0.57914(18) 0.46813(6) 0.71610(18) 0.0555 1.0000 Uani D U . . . . .
Cl1 Cl 0.66227(7) 0.45244(3) 0.67967(12) 0.0853 0.8500 Uani D U . . . . .
Cl2 Cl 0.55990(12) 0.45935(3) 0.82292(9) 0.1010 0.8500 Uani D U . . . . .
Cl3 Cl 0.49962(8) 0.46422(3) 0.64892(11) 0.0865 0.8500 Uani D U . . . . .
Cl4 Cl 0.5408(6) 0.45449(12) 0.6162(3) 0.0940 0.1500 Uani D U . . . . .
Cl5 Cl 0.6547(3) 0.44748(10) 0.7485(5) 0.0668 0.1500 Uani D U . . . . .
Cl6 Cl 0.5018(4) 0.4651(2) 0.7914(5) 0.1184 0.1500 Uani D U . . . . .
H21 H 0.4943 0.5874 0.1594 0.0336 1.0000 Uiso R . . . . . .
H31 H 0.3510 0.5948 0.0667 0.0330 1.0000 Uiso R . . . . . .
H41 H 0.3138 0.6258 0.1604 0.0316 1.0000 Uiso R . . . . . .
H51 H 0.3852 0.6413 0.0474 0.0377 1.0000 Uiso R . . . . . .
H61 H 0.5258 0.6451 0.0439 0.0388 1.0000 Uiso R . . . . . .
H62 H 0.5315 0.6316 0.1356 0.0392 1.0000 Uiso R . . . . . .
H81 H 0.6357 0.6047 0.1376 0.0500 1.0000 Uiso R . . . . . .
H91 H 0.7623 0.5886 0.1005 0.0637 1.0000 Uiso R . . . . . .
H101 H 0.7807 0.5719 -0.0402 0.0701 1.0000 Uiso R . . . . . .
H111 H 0.6797 0.5751 -0.1349 0.0683 1.0000 Uiso R . . . . . .
H141 H 0.5370 0.5233 -0.0189 0.0645 1.0000 Uiso R . . . . . .
H151 H 0.6401 0.4967 0.0280 0.0742 1.0000 Uiso R . . . . . .
H161 H 0.6952 0.5032 0.1668 0.0763 1.0000 Uiso R . . . . . .
H171 H 0.6481 0.5352 0.2516 0.0693 1.0000 Uiso R . . . . . .
H191 H 0.4263 0.5654 0.2565 0.0466 1.0000 Uiso R . . . . . .
H201 H 0.3585 0.5348 0.3363 0.0512 1.0000 Uiso R . . . . . .
H221 H 0.1628 0.5474 0.1905 0.0529 1.0000 Uiso R . . . . . .
H231 H 0.2292 0.5783 0.1151 0.0432 1.0000 Uiso R . . . . . .
H261 H 0.4179 0.6294 0.4226 0.0447 1.0000 Uiso R . . . . . .
H271 H 0.3240 0.6434 0.5267 0.0556 1.0000 Uiso R . . . . . .
H281 H 0.1960 0.6523 0.4808 0.0582 1.0000 Uiso R . . . . . .
H291 H 0.1630 0.6457 0.3389 0.0603 1.0000 Uiso R . . . . . .
H311 H 0.2918 0.6697 0.1230 0.0513 1.0000 Uiso R . . . . . .
H321 H 0.2782 0.7103 0.1794 0.0545 1.0000 Uiso R . . . . . .
H341 H 0.5134 0.7130 0.2255 0.0500 1.0000 Uiso R . . . . . .
H351 H 0.5260 0.6729 0.1666 0.0474 1.0000 Uiso R . . . . . .
H411 H 0.5942 0.4863 0.7122 0.0920 1.0000 Uiso R . . . . . .
H1 H 0.4829 0.5989 -0.0751 0.0481 1.0000 Uiso R . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.09364(6)
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 . C21 . 1.899(2) yes
Br2 . C33 . 1.904(2) yes
O1 . C1 . 1.418(3) yes
O1 . H1 . 0.851 no
O2 . C12 . 1.208(3) yes
O3 . C24 . 1.214(3) yes
N1 . C7 . 1.337(3) yes
N1 . C11 . 1.347(4) yes
N2 . C13 . 1.342(3) yes
N2 . C17 . 1.339(4) yes
N3 . C25 . 1.334(3) yes
N3 . C29 . 1.322(3) yes
C1 . C2 . 1.562(3) yes
C1 . C6 . 1.535(3) yes
C1 . C7 . 1.525(3) yes
C2 . C3 . 1.534(3) yes
C2 . C12 . 1.519(3) yes
C2 . H21 . 1.003 no
C3 . C4 . 1.551(3) yes
C3 . C18 . 1.514(3) yes
C3 . H31 . 0.977 no
C4 . C5 . 1.557(3) yes
C4 . C24 . 1.521(3) yes
C4 . H41 . 0.991 no
C5 . C6 . 1.527(3) yes
C5 . C30 . 1.525(3) yes
C5 . H51 . 0.993 no
C6 . H61 . 0.984 no
C6 . H62 . 0.990 no
C7 . C8 . 1.379(4) yes
C8 . C9 . 1.388(4) yes
C8 . H81 . 0.954 no
C9 . C10 . 1.387(5) yes
C9 . H91 . 0.947 no
C10 . C11 . 1.346(5) yes
C10 . H101 . 0.946 no
C11 . H111 . 0.923 no
C12 . C13 . 1.503(3) yes
C13 . C14 . 1.381(4) yes
C14 . C15 . 1.380(4) yes
C14 . H141 . 0.963 no
C15 . C16 . 1.381(5) yes
C15 . H151 . 0.935 no
C16 . C17 . 1.383(5) yes
C16 . H161 . 0.948 no
C17 . H171 . 0.960 no
C18 . C19 . 1.397(3) yes
C18 . C23 . 1.390(3) yes
C19 . C20 . 1.390(3) yes
C19 . H191 . 0.942 no
C20 . C21 . 1.366(4) yes
C20 . H201 . 0.955 no
C21 . C22 . 1.390(4) yes
C22 . C23 . 1.379(4) yes
C22 . H221 . 0.948 no
C23 . H231 . 0.953 no
C24 . C25 . 1.514(3) yes
C25 . C26 . 1.385(3) yes
C26 . C27 . 1.395(4) yes
C26 . H261 . 0.951 no
C27 . C28 . 1.366(4) yes
C27 . H271 . 0.955 no
C28 . C29 . 1.383(4) yes
C28 . H281 . 0.934 no
C29 . H291 . 0.921 no
C30 . C31 . 1.391(4) yes
C30 . C35 . 1.381(4) yes
C31 . C32 . 1.388(4) yes
C31 . H311 . 0.952 no
C32 . C33 . 1.392(4) yes
C32 . H321 . 0.932 no
C33 . C34 . 1.365(4) yes
C34 . C35 . 1.393(3) yes
C34 . H341 . 0.947 no
C35 . H351 . 0.934 no
C41 . Cl1 . 1.726(3) yes
C41 . Cl2 . 1.749(3) yes
C41 . Cl3 . 1.710(3) yes
C41 . Cl4 . 1.827(6) yes
C41 . Cl5 . 1.756(5) yes
C41 . Cl6 . 1.756(6) yes
C41 . H411 . 1.002 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
C1 . O1 . H1 . 106.9 no
C7 . N1 . C11 . 117.0(3) yes
C13 . N2 . C17 . 117.1(3) yes
C25 . N3 . C29 . 117.3(2) yes
O1 . C1 . C2 . 110.41(19) yes
O1 . C1 . C6 . 107.55(19) yes
C2 . C1 . C6 . 108.70(17) yes
O1 . C1 . C7 . 109.72(17) yes
C2 . C1 . C7 . 108.92(18) yes
C6 . C1 . C7 . 111.5(2) yes
C1 . C2 . C3 . 110.00(17) yes
C1 . C2 . C12 . 109.21(17) yes
C3 . C2 . C12 . 110.86(18) yes
C1 . C2 . H21 . 109.2 no
C3 . C2 . H21 . 107.8 no
C12 . C2 . H21 . 109.7 no
C2 . C3 . C4 . 112.65(17) yes
C2 . C3 . C18 . 112.46(17) yes
C4 . C3 . C18 . 112.28(17) yes
C2 . C3 . H31 . 106.2 no
C4 . C3 . H31 . 106.4 no
C18 . C3 . H31 . 106.2 no
C3 . C4 . C5 . 110.43(17) yes
C3 . C4 . C24 . 112.18(16) yes
C5 . C4 . C24 . 111.56(17) yes
C3 . C4 . H41 . 107.2 no
C5 . C4 . H41 . 108.4 no
C24 . C4 . H41 . 106.9 no
C4 . C5 . C6 . 112.89(17) yes
C4 . C5 . C30 . 111.06(18) yes
C6 . C5 . C30 . 113.20(19) yes
C4 . C5 . H51 . 105.5 no
C6 . C5 . H51 . 108.2 no
C30 . C5 . H51 . 105.4 no
C1 . C6 . C5 . 111.48(19) yes
C1 . C6 . H61 . 110.9 no
C5 . C6 . H61 . 109.9 no
C1 . C6 . H62 . 107.2 no
C5 . C6 . H62 . 109.4 no
H61 . C6 . H62 . 107.8 no
C1 . C7 . N1 . 114.9(2) yes
C1 . C7 . C8 . 122.6(2) yes
N1 . C7 . C8 . 122.4(2) yes
C7 . C8 . C9 . 118.9(3) yes
C7 . C8 . H81 . 119.4 no
C9 . C8 . H81 . 121.7 no
C8 . C9 . C10 . 118.8(3) yes
C8 . C9 . H91 . 120.5 no
C10 . C9 . H91 . 120.7 no
C9 . C10 . C11 . 118.0(3) yes
C9 . C10 . H101 . 122.2 no
C11 . C10 . H101 . 119.8 no
N1 . C11 . C10 . 124.7(3) yes
N1 . C11 . H111 . 117.0 no
C10 . C11 . H111 . 118.3 no
C2 . C12 . O2 . 122.0(2) yes
C2 . C12 . C13 . 118.0(2) yes
O2 . C12 . C13 . 120.0(2) yes
C12 . C13 . N2 . 117.1(2) yes
C12 . C13 . C14 . 119.6(2) yes
N2 . C13 . C14 . 123.3(2) yes
C13 . C14 . C15 . 119.0(3) yes
C13 . C14 . H141 . 120.0 no
C15 . C14 . H141 . 121.0 no
C14 . C15 . C16 . 118.3(3) yes
C14 . C15 . H151 . 120.8 no
C16 . C15 . H151 . 120.9 no
C15 . C16 . C17 . 119.2(3) yes
C15 . C16 . H161 . 122.3 no
C17 . C16 . H161 . 118.4 no
C16 . C17 . N2 . 123.0(3) yes
C16 . C17 . H171 . 118.4 no
N2 . C17 . H171 . 118.6 no
C3 . C18 . C19 . 122.7(2) yes
C3 . C18 . C23 . 119.7(2) yes
C19 . C18 . C23 . 117.6(2) yes
C18 . C19 . C20 . 121.3(2) yes
C18 . C19 . H191 . 119.3 no
C20 . C19 . H191 . 119.3 no
C19 . C20 . C21 . 119.0(2) yes
C19 . C20 . H201 . 120.9 no
C21 . C20 . H201 . 120.1 no
Br1 . C21 . C20 . 119.7(2) yes
Br1 . C21 . C22 . 118.8(2) yes
C20 . C21 . C22 . 121.5(2) yes
C21 . C22 . C23 . 118.6(2) yes
C21 . C22 . H221 . 121.4 no
C23 . C22 . H221 . 120.0 no
C18 . C23 . C22 . 121.9(2) yes
C18 . C23 . H231 . 119.9 no
C22 . C23 . H231 . 118.2 no
C4 . C24 . O3 . 122.84(19) yes
C4 . C24 . C25 . 117.90(18) yes
O3 . C24 . C25 . 119.25(19) yes
C24 . C25 . N3 . 117.8(2) yes
C24 . C25 . C26 . 119.0(2) yes
N3 . C25 . C26 . 123.2(2) yes
C25 . C26 . C27 . 118.1(2) yes
C25 . C26 . H261 . 121.2 no
C27 . C26 . H261 . 120.7 no
C26 . C27 . C28 . 119.0(3) yes
C26 . C27 . H271 . 121.5 no
C28 . C27 . H271 . 119.5 no
C27 . C28 . C29 . 118.3(2) yes
C27 . C28 . H281 . 121.2 no
C29 . C28 . H281 . 120.5 no
C28 . C29 . N3 . 124.1(3) yes
C28 . C29 . H291 . 118.4 no
N3 . C29 . H291 . 117.5 no
C5 . C30 . C31 . 118.6(2) yes
C5 . C30 . C35 . 123.0(2) yes
C31 . C30 . C35 . 118.3(2) yes
C30 . C31 . C32 . 121.2(3) yes
C30 . C31 . H311 . 117.9 no
C32 . C31 . H311 . 120.9 no
C31 . C32 . C33 . 118.7(3) yes
C31 . C32 . H321 . 119.8 no
C33 . C32 . H321 . 121.4 no
Br2 . C33 . C32 . 119.4(2) yes
Br2 . C33 . C34 . 119.4(2) yes
C32 . C33 . C34 . 121.2(2) yes
C33 . C34 . C35 . 119.1(3) yes
C33 . C34 . H341 . 119.7 no
C35 . C34 . H341 . 121.2 no
C34 . C35 . C30 . 121.4(2) yes
C34 . C35 . H351 . 118.7 no
C30 . C35 . H351 . 119.9 no
Cl1 . C41 . Cl2 . 109.31(18) yes
Cl1 . C41 . Cl3 . 112.25(19) yes
Cl2 . C41 . Cl3 . 113.45(19) yes
Cl4 . C41 . Cl5 . 104.5(4) yes
Cl4 . C41 . Cl6 . 105.3(4) yes
Cl5 . C41 . Cl6 . 107.0(4) yes
Cl1 . C41 . H411 . 104.0 no
Cl2 . C41 . H411 . 111.2 no
Cl3 . C41 . H411 . 106.2 no
Cl4 . C41 . H411 . 115.0 no
Cl5 . C41 . H411 . 116.0 no
Cl6 . C41 . H411 . 108.3 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
C2 . H21 . O3 . 123 1.00 2.47 3.130(4) yes
C6 . H62 . O3 . 121 0.99 2.52 3.142(4) yes
O1 . H1 . N1 . 122 0.85 2.03 2.581(4) yes

# Attachment 'compound_4.cif'

data_gq1_223k
_database_code_depnum_ccdc_archive 'CCDC 708559'
_audit_creation_date             08-05-29
_audit_creation_method           CRYSTALS_ver_12.84

_oxford_structure_analysis_title 'gq1_223k_0m in P-1'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   9.8089(4)
_cell_length_b                   11.1946(4)
_cell_length_c                   14.5862(6)
_cell_angle_alpha                71.544(2)
_cell_angle_beta                 88.809(2)
_cell_angle_gamma                80.093(2)
_cell_volume                     1495.66(10)

_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
-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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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            2

# Given Formula = C33 H21 N6 O1
# Dc = 1.15 Fooo = 616.00 Mu = 0.73 M = 517.57
# Found Formula = C37 H27 N5 O3
# Dc = 1.31 FOOO = 616.00 Mu = 0.85 M = 589.65

_chemical_formula_sum            'C37 H27 N5 O3'
_chemical_formula_moiety         'C37 H27 N5 O3'
_chemical_compound_source        ?
_chemical_formula_weight         589.65

_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    223

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.04
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_max          0.29

_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.085

# Sheldrick geometric approximatio 0.99 1.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  1.00
# For a Kappa CCD, set Tmin to 1.0 and
# Tmax to the ratio of max:min frame scales in scale_all.log
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  ?
_diffrn_standards_interval_count ?
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      223
_diffrn_reflns_number            53005
_reflns_number_total             8757
_diffrn_reflns_av_R_equivalents  0.028
# Number of reflections with Friedels Law is 8757
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 8806

_diffrn_reflns_theta_min         2.109
_diffrn_reflns_theta_max         30.111
_diffrn_measured_fraction_theta_max 0.993

_diffrn_reflns_theta_full        29.508
_diffrn_measured_fraction_theta_full 0.995

_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              -14
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.21
_refine_diff_density_max         0.31

_refine_ls_number_reflns         5817
_refine_ls_number_restraints     0
_refine_ls_number_parameters     406

#_refine_ls_R_factor_ref 0.0418
_refine_ls_wR_factor_ref         0.0495
_refine_ls_goodness_of_fit_ref   1.0914

#_reflns_number_all 8701
_refine_ls_R_factor_all          0.0597
_refine_ls_wR_factor_all         0.0690

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.0σ(I)
_reflns_number_gt                5817
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_gt          0.0495

_refine_ls_shift/su_max          0.000386

# 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 F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
0.601 0.537 0.267
;

_publ_section_abstract           
# Text of the abstract
# (a) The Abstract must be self-contained and comprehensible
# without the rest of the paper. This means no references
# to atom names or to compound numbers; compounds must be
# identified as the title compound, or by name or by some other
# means such as derivatives of each other (e.g. "the
# corresponding ketone").
# (b) The chemical formula of "the title compound" must be given.
# (c) Any crystallographic molecular symmetry should be
# mentioned, and also the presence of more than one molecule
# in the asymmetric unit (i.e. anything other than Z'=1).
;
?
;
_publ_section_comment            
# Text of the paper
# Note that atoms are referenced as N2, not N(2) or N~2~
# If text containing () occur within (), the outer ones should be []
# Figures should be referenced as Fih.
;
?
;
_publ_section_acknowledgements   # Acknowledgments
;
?
;
_publ_section_figure_captions    
# Captions to figures - Start each caption on a new line after a blank line
;
Fig. 1.
The title compound with displacement ellipsoids drawn at the 50%
probability level. H atoms are shown as spheres of
arbitary radius.

;

_publ_section_exptl_refinement   
# Some potentially useful phrases are donated by Bill Clegg:
;
In the absence of significant anomalous scattering, Friedel pairs were
merged.

The absolute configuration was arbitrarily assigned.

The relatively large ratio of minimum to maximum corrections applied
in the multiscan process (1:nnn) reflect changes in the illuminated
volume of the crystal.

Changes in illuminated volume were kept to a minimum, and were
taken into account (Görbitz, 1999) by the multi-scan inter-frame
scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).

Görbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.

The H atoms were all located in a difference map, but those
attached to carbon atoms 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--0.98,
N---H in the range 0.86--0.89
N---H to 0.86
O---H = 0.82
Å)
and
Uiso(H) (in the range 1.2-1.5 times Ueq of the parent atom),
after which the positions were refined with riding constraints.

;

_publ_section_exptl_prep         
# Brief details or a reference. Include solvent if known
;
?
;

# End of 'script/refcif.dat'

# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R.,
Munksgaard, Copenhagen, 291-294.

Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
O1 O 0.54688(9) 0.62983(9) 0.33540(7) 0.0350 1.0000 Uani . . . . . .
O2 O 0.34808(10) 0.53307(11) 0.46786(7) 0.0418 1.0000 Uani . . . . . .
O3 O 0.38926(10) 0.37793(10) 0.15327(7) 0.0412 1.0000 Uani . . . . . .
N1 N 0.26372(12) 0.73920(11) 0.15785(9) 0.0411 1.0000 Uani . . . . . .
N2 N 0.07271(11) 0.56392(11) 0.30826(8) 0.0351 1.0000 Uani . . . . . .
N3 N 0.14098(17) -0.14051(14) 0.55853(11) 0.0579 1.0000 Uani . . . . . .
N4 N 0.65564(17) 0.11226(13) 0.22967(10) 0.0542 1.0000 Uani . . . . . .
N5 N 1.15591(14) 0.26941(13) -0.05213(10) 0.0496 1.0000 Uani . . . . . .
C1 C 0.45724(11) 0.61443(11) 0.26614(8) 0.0255 1.0000 Uani . . . . . .
C2 C 0.37073(11) 0.50730(10) 0.31197(8) 0.0234 1.0000 Uani . . . . . .
C3 C 0.46403(11) 0.37569(10) 0.35286(8) 0.0235 1.0000 Uani . . . . . .
C4 C 0.56297(11) 0.34073(11) 0.27758(8) 0.0248 1.0000 Uani . . . . . .
C5 C 0.64605(11) 0.45107(11) 0.23294(8) 0.0262 1.0000 Uani . . . . . .
C6 C 0.54934(12) 0.57913(11) 0.18874(8) 0.0276 1.0000 Uani . . . . . .
C7 C 0.35830(13) 0.74043(11) 0.22129(9) 0.0299 1.0000 Uani . . . . . .
C8 C 0.3680(2) 0.84918(15) 0.24544(13) 0.0517 1.0000 Uani . . . . . .
C9 C 0.2706(3) 0.95859(17) 0.20481(17) 0.0705 1.0000 Uani . . . . . .
C10 C 0.1680(2) 0.95579(16) 0.14339(15) 0.0633 1.0000 Uani . . . . . .
C11 C 0.16992(18) 0.84560(15) 0.12086(14) 0.0551 1.0000 Uani . . . . . .
C12 C 0.28919(11) 0.54000(11) 0.39317(8) 0.0263 1.0000 Uani . . . . . .
C13 C 0.13652(11) 0.58561(11) 0.37996(8) 0.0270 1.0000 Uani . . . . . .
C14 C 0.07015(14) 0.64599(14) 0.44214(11) 0.0392 1.0000 Uani . . . . . .
C15 C -0.07171(15) 0.68669(16) 0.42899(14) 0.0513 1.0000 Uani . . . . . .
C16 C -0.13930(14) 0.66657(16) 0.35572(13) 0.0484 1.0000 Uani . . . . . .
C17 C -0.06425(14) 0.60523(16) 0.29738(12) 0.0431 1.0000 Uani . . . . . .
C18 C 0.38336(11) 0.26954(11) 0.39982(8) 0.0249 1.0000 Uani . . . . . .
C19 C 0.26747(13) 0.25216(13) 0.35436(9) 0.0337 1.0000 Uani . . . . . .
C20 C 0.20380(14) 0.14746(13) 0.39584(10) 0.0361 1.0000 Uani . . . . . .
C21 C 0.25311(13) 0.05988(12) 0.48481(9) 0.0324 1.0000 Uani . . . . . .
C22 C 0.18913(16) -0.05118(14) 0.52652(11) 0.0412 1.0000 Uani . . . . . .
C23 C 0.36358(13) 0.07904(12) 0.53314(9) 0.0329 1.0000 Uani . . . . . .
C24 C 0.42803(12) 0.18298(12) 0.49043(8) 0.0290 1.0000 Uani . . . . . .
C25 C 0.49284(13) 0.31080(11) 0.19756(8) 0.0289 1.0000 Uani . . . . . .
C26 C 0.55969(15) 0.19724(12) 0.16904(9) 0.0359 1.0000 Uani . . . . . .
C27 C 0.5225(2) 0.18961(17) 0.07960(12) 0.0518 1.0000 Uani . . . . . .
C28 C 0.5910(3) 0.0891(2) 0.05176(16) 0.0700 1.0000 Uani . . . . . .
C29 C 0.6879(3) -0.0004(2) 0.1141(2) 0.0829 1.0000 Uani . . . . . .
C30 C 0.7170(3) 0.01384(19) 0.20144(17) 0.0776 1.0000 Uani . . . . . .
C31 C 0.75450(11) 0.41591(11) 0.16585(8) 0.0266 1.0000 Uani . . . . . .
C32 C 0.72895(13) 0.44265(13) 0.06733(9) 0.0319 1.0000 Uani . . . . . .
C33 C 0.83004(13) 0.40544(13) 0.00887(9) 0.0334 1.0000 Uani . . . . . .
C34 C 0.95999(13) 0.34231(11) 0.04967(9) 0.0302 1.0000 Uani . . . . . .
C35 C 1.06846(14) 0.30337(13) -0.00881(10) 0.0357 1.0000 Uani . . . . . .
C36 C 0.98778(14) 0.31580(14) 0.14772(10) 0.0376 1.0000 Uani . . . . . .
C37 C 0.88537(13) 0.35185(13) 0.20516(9) 0.0355 1.0000 Uani . . . . . .
H1 H 0.5250 0.5956 0.3904 0.0548 1.0000 Uiso R . . . . .
H21 H 0.3043 0.5046 0.2615 0.0268 1.0000 Uiso R . . . . .
H31 H 0.5236 0.3822 0.4042 0.0268 1.0000 Uiso R . . . . .
H41 H 0.6297 0.2631 0.3101 0.0283 1.0000 Uiso R . . . . .
H51 H 0.6972 0.4589 0.2863 0.0304 1.0000 Uiso R . . . . .
H61 H 0.4926 0.5771 0.1361 0.0318 1.0000 Uiso R . . . . .
H62 H 0.6059 0.6480 0.1622 0.0317 1.0000 Uiso R . . . . .
H81 H 0.4384 0.8476 0.2902 0.0640 1.0000 Uiso R . . . . .
H91 H 0.2768 1.0327 0.2211 0.0823 1.0000 Uiso R . . . . .
H101 H 0.0973 1.0268 0.1151 0.0712 1.0000 Uiso R . . . . .
H111 H 0.1006 0.8448 0.0750 0.0613 1.0000 Uiso R . . . . .
H141 H 0.1196 0.6604 0.4894 0.0478 1.0000 Uiso R . . . . .
H151 H -0.1186 0.7285 0.4689 0.0608 1.0000 Uiso R . . . . .
H161 H -0.2362 0.6911 0.3468 0.0542 1.0000 Uiso R . . . . .
H171 H -0.1106 0.5914 0.2463 0.0511 1.0000 Uiso R . . . . .
H191 H 0.2332 0.3127 0.2946 0.0397 1.0000 Uiso R . . . . .
H201 H 0.1292 0.1360 0.3641 0.0431 1.0000 Uiso R . . . . .
H231 H 0.3956 0.0206 0.5953 0.0370 1.0000 Uiso R . . . . .
H241 H 0.5019 0.1959 0.5241 0.0333 1.0000 Uiso R . . . . .
H271 H 0.4503 0.2507 0.0380 0.0695 1.0000 Uiso R . . . . .
H281 H 0.5666 0.0800 -0.0108 0.0929 1.0000 Uiso R . . . . .
H291 H 0.7314 -0.0726 0.0952 0.1073 1.0000 Uiso R . . . . .
H301 H 0.7871 -0.0451 0.2458 0.0934 1.0000 Uiso R . . . . .
H321 H 0.6442 0.4851 0.0403 0.0370 1.0000 Uiso R . . . . .
H331 H 0.8101 0.4219 -0.0581 0.0387 1.0000 Uiso R . . . . .
H361 H 1.0756 0.2767 0.1754 0.0435 1.0000 Uiso R . . . . .
H371 H 0.9026 0.3327 0.2703 0.0400 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.6335(9)
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
O1 . C1 . 1.4222(14) yes
O1 . H1 . 0.814 no
O2 . C12 . 1.2180(14) yes
O3 . C25 . 1.2130(15) yes
N1 . C7 . 1.3286(17) yes
N1 . C11 . 1.3391(18) yes
N2 . C13 . 1.3360(16) yes
N2 . C17 . 1.3389(16) yes
N3 . C22 . 1.1396(19) yes
N4 . C26 . 1.329(2) yes
N4 . C30 . 1.340(2) yes
N5 . C35 . 1.1388(17) yes
C1 . C2 . 1.5570(15) yes
C1 . C6 . 1.5374(16) yes
C1 . C7 . 1.5266(16) yes
C2 . C3 . 1.5383(15) yes
C2 . C12 . 1.5202(15) yes
C2 . H21 . 1.004 no
C3 . C4 . 1.5484(15) yes
C3 . C18 . 1.5142(15) yes
C3 . H31 . 0.988 no
C4 . C5 . 1.5585(16) yes
C4 . C25 . 1.5194(16) yes
C4 . H41 . 0.982 no
C5 . C6 . 1.5306(16) yes
C5 . C31 . 1.5168(15) yes
C5 . H51 . 0.969 no
C6 . H61 . 0.965 no
C6 . H62 . 1.000 no
C7 . C8 . 1.3886(19) yes
C8 . C9 . 1.387(2) yes
C8 . H81 . 0.954 no
C9 . C10 . 1.372(3) yes
C9 . H91 . 0.944 no
C10 . C11 . 1.371(3) yes
C10 . H101 . 0.948 no
C11 . H111 . 0.967 no
C12 . C13 . 1.4923(15) yes
C13 . C14 . 1.3840(17) yes
C14 . C15 . 1.385(2) yes
C14 . H141 . 0.921 no
C15 . C16 . 1.366(2) yes
C15 . H151 . 0.926 no
C16 . C17 . 1.381(2) yes
C16 . H161 . 0.943 no
C17 . H171 . 0.947 no
C18 . C19 . 1.3996(16) yes
C18 . C24 . 1.3946(15) yes
C19 . C20 . 1.3846(18) yes
C19 . H191 . 0.945 no
C20 . C21 . 1.3916(18) yes
C20 . H201 . 0.921 no
C21 . C22 . 1.4435(18) yes
C21 . C23 . 1.3873(19) yes
C23 . C24 . 1.3854(17) yes
C23 . H231 . 0.956 no
C24 . H241 . 0.940 no
C25 . C26 . 1.5019(17) yes
C26 . C27 . 1.394(2) yes
C27 . C28 . 1.378(3) yes
C27 . H271 . 0.962 no
C28 . C29 . 1.366(4) yes
C28 . H281 . 0.989 no
C29 . C30 . 1.374(3) yes
C29 . H291 . 0.965 no
C30 . H301 . 0.959 no
C31 . C32 . 1.3907(16) yes
C31 . C37 . 1.3944(16) yes
C32 . C33 . 1.3898(17) yes
C32 . H321 . 0.912 no
C33 . C34 . 1.3906(18) yes
C33 . H331 . 0.952 no
C34 . C35 . 1.4449(17) yes
C34 . C36 . 1.3883(18) yes
C36 . C37 . 1.3834(17) yes
C36 . H361 . 0.932 no
C37 . H371 . 0.918 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
C1 . O1 . H1 . 111.5 no
C7 . N1 . C11 . 117.81(13) yes
C13 . N2 . C17 . 116.25(12) yes
C26 . N4 . C30 . 116.41(17) yes
O1 . C1 . C2 . 112.20(9) yes
O1 . C1 . C6 . 106.94(9) yes
C2 . C1 . C6 . 109.49(9) yes
O1 . C1 . C7 . 108.90(9) yes
C2 . C1 . C7 . 108.80(9) yes
C6 . C1 . C7 . 110.51(9) yes
C1 . C2 . C3 . 111.54(8) yes
C1 . C2 . C12 . 108.19(9) yes
C3 . C2 . C12 . 109.36(9) yes
C1 . C2 . H21 . 109.2 no
C3 . C2 . H21 . 109.5 no
C12 . C2 . H21 . 109.1 no
C2 . C3 . C4 . 113.03(9) yes
C2 . C3 . C18 . 112.94(9) yes
C4 . C3 . C18 . 111.00(9) yes
C2 . C3 . H31 . 106.2 no
C4 . C3 . H31 . 106.2 no
C18 . C3 . H31 . 106.9 no
C3 . C4 . C5 . 109.20(9) yes
C3 . C4 . C25 . 114.85(9) yes
C5 . C4 . C25 . 109.88(9) yes
C3 . C4 . H41 . 109.3 no
C5 . C4 . H41 . 107.8 no
C25 . C4 . H41 . 105.5 no
C4 . C5 . C6 . 111.42(9) yes
C4 . C5 . C31 . 111.24(9) yes
C6 . C5 . C31 . 114.83(9) yes
C4 . C5 . H51 . 106.2 no
C6 . C5 . H51 . 106.8 no
C31 . C5 . H51 . 105.7 no
C1 . C6 . C5 . 110.65(9) yes
C1 . C6 . H61 . 110.1 no
C5 . C6 . H61 . 111.2 no
C1 . C6 . H62 . 107.8 no
C5 . C6 . H62 . 109.3 no
H61 . C6 . H62 . 107.7 no
C1 . C7 . N1 . 115.85(10) yes
C1 . C7 . C8 . 121.61(12) yes
N1 . C7 . C8 . 122.54(13) yes
C7 . C8 . C9 . 118.23(17) yes
C7 . C8 . H81 . 120.6 no
C9 . C8 . H81 . 121.2 no
C8 . C9 . C10 . 119.44(17) yes
C8 . C9 . H91 . 118.5 no
C10 . C9 . H91 . 122.1 no
C9 . C10 . C11 . 118.16(15) yes
C9 . C10 . H101 . 123.0 no
C11 . C10 . H101 . 118.8 no
C10 . C11 . N1 . 123.65(17) yes
C10 . C11 . H111 . 118.4 no
N1 . C11 . H111 . 118.0 no
C2 . C12 . O2 . 120.52(10) yes
C2 . C12 . C13 . 119.79(10) yes
O2 . C12 . C13 . 119.65(10) yes
C12 . C13 . N2 . 116.94(10) yes
C12 . C13 . C14 . 118.76(11) yes
N2 . C13 . C14 . 124.30(11) yes
C13 . C14 . C15 . 117.77(14) yes
C13 . C14 . H141 . 120.7 no
C15 . C14 . H141 . 121.5 no
C14 . C15 . C16 . 119.10(14) yes
C14 . C15 . H151 . 119.7 no
C16 . C15 . H151 . 121.2 no
C15 . C16 . C17 . 118.98(13) yes
C15 . C16 . H161 . 120.4 no
C17 . C16 . H161 . 120.6 no
C16 . C17 . N2 . 123.59(14) yes
C16 . C17 . H171 . 119.3 no
N2 . C17 . H171 . 117.1 no
C3 . C18 . C19 . 122.46(10) yes
C3 . C18 . C24 . 119.18(10) yes
C19 . C18 . C24 . 118.33(11) yes
C18 . C19 . C20 . 120.73(11) yes
C18 . C19 . H191 . 119.1 no
C20 . C19 . H191 . 120.1 no
C19 . C20 . C21 . 119.88(12) yes
C19 . C20 . H201 . 119.7 no
C21 . C20 . H201 . 120.4 no
C20 . C21 . C22 . 119.75(12) yes
C20 . C21 . C23 . 120.15(11) yes
C22 . C21 . C23 . 120.10(12) yes
C21 . C22 . N3 . 178.36(17) yes
C21 . C23 . C24 . 119.56(11) yes
C21 . C23 . H231 . 120.3 no
C24 . C23 . H231 . 120.1 no
C18 . C24 . C23 . 121.24(11) yes
C18 . C24 . H241 . 119.8 no
C23 . C24 . H241 . 119.0 no
C4 . C25 . O3 . 122.70(11) yes
C4 . C25 . C26 . 118.16(11) yes
O3 . C25 . C26 . 119.06(12) yes
C25 . C26 . N4 . 117.40(12) yes
C25 . C26 . C27 . 118.66(14) yes
N4 . C26 . C27 . 123.88(14) yes
C26 . C27 . C28 . 118.01(19) yes
C26 . C27 . H271 . 122.3 no
C28 . C27 . H271 . 119.7 no
C27 . C28 . C29 . 118.75(19) yes
C27 . C28 . H281 . 120.3 no
C29 . C28 . H281 . 120.9 no
C28 . C29 . C30 . 119.37(18) yes
C28 . C29 . H291 . 117.9 no
C30 . C29 . H291 . 122.7 no
C29 . C30 . N4 . 123.5(2) yes
C29 . C30 . H301 . 121.6 no
N4 . C30 . H301 . 114.8 no
C5 . C31 . C32 . 123.14(10) yes
C5 . C31 . C37 . 118.39(10) yes
C32 . C31 . C37 . 118.46(11) yes
C31 . C32 . C33 . 121.32(11) yes
C31 . C32 . H321 . 119.6 no
C33 . C32 . H321 . 119.1 no
C32 . C33 . C34 . 119.14(11) yes
C32 . C33 . H331 . 120.4 no
C34 . C33 . H331 . 120.5 no
C33 . C34 . C35 . 120.87(12) yes
C33 . C34 . C36 . 120.35(11) yes
C35 . C34 . C36 . 118.78(12) yes
C34 . C35 . N5 . 177.64(15) yes
C34 . C36 . C37 . 119.78(12) yes
C34 . C36 . H361 . 121.1 no
C37 . C36 . H361 . 119.1 no
C31 . C37 . C36 . 120.94(12) yes
C31 . C37 . H371 . 119.0 no
C36 . C37 . H371 . 120.1 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
O1 . H1 . O2 . 140 0.81 2.15 2.820(2) yes


