# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1I
_database_code_depnum_ccdc_archive 'CCDC 2050536'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
Refinement proceeded smoothly with no restraints necessary (other than those on
O-H bond lengths and angles.

The structure has a Z' of 5.

C-H hydrogen atoms were generally visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. O-H hydrogen atoms 
were visible in the Fourier difference map and were refined with restraints on
bond lengths and angles.
;

_cell_length_a                   8.1689(2)
_cell_length_b                   30.7155(7)
_cell_length_c                   16.3945(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.292(3)
_cell_angle_gamma                90
_cell_volume                     4003.38(10)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,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'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            20

_chemical_formula_sum            'C6 H8 I1 N1 O1'
_chemical_formula_moiety         'C6 H8 N O, I'
_chemical_compound_source        syntheszied
_chemical_formula_weight         237.04


_cell_measurement_reflns_used    11077
_cell_measurement_theta_min      4
_cell_measurement_theta_max      29
_cell_measurement_temperature    150

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.060
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_max          0.540

_exptl_crystal_density_diffrn    1.966
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2240
_exptl_absorpt_coefficient_mu    3.925

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.737
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_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            38419
_reflns_number_total             8122
_diffrn_reflns_av_R_equivalents  0.040

_diffrn_reflns_theta_min         3.264
_diffrn_reflns_theta_max         26.315
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        26.315
_diffrn_measured_fraction_theta_full 0.998

_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -10
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              38
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   2.46
_oxford_diffrn_Wilson_scale      3.62

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -1.18
_refine_diff_density_max         1.17


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         8104
_refine_ls_number_restraints     5
_refine_ls_number_parameters     421
_oxford_refine_ls_R_factor_ref   0.0444
_refine_ls_wR_factor_ref         0.0514
_refine_ls_goodness_of_fit_ref   0.9294
_refine_ls_shift/su_max          0.0012222
_refine_ls_shift/su_mean         0.0000406

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        8104
_refine_ls_R_factor_all          0.0444
_refine_ls_wR_factor_all         0.0514

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6503
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_gt          0.0441

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    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: 
 163. 216. 124. 48.1 12.8 
;

# 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
O1 O 0.2651(5) 0.70277(13) 0.8605(3) 0.0487 1.0000 Uani D . . . . .
C2 C 0.1668(6) 0.70648(17) 0.9154(3) 0.0302 1.0000 Uani . . . . . .
C3 C 0.1408(5) 0.74840(16) 0.9395(3) 0.0279 1.0000 Uani . . . . . .
N4 N 0.0484(5) 0.75583(14) 0.9951(2) 0.0307 1.0000 Uani . . . . . .
C5 C -0.0223(7) 0.7232(2) 1.0293(3) 0.0437 1.0000 Uani . . . . . .
C6 C 0.0020(8) 0.6811(2) 1.0073(4) 0.0468 1.0000 Uani . . . . . .
C7 C 0.0961(6) 0.67227(18) 0.9497(3) 0.0386 1.0000 Uani . . . . . .
C8 C 0.0241(7) 0.80116(19) 1.0196(4) 0.0509 1.0000 Uani . . . . . .
O11 O 0.9011(5) 0.74679(11) 0.7089(2) 0.0377 1.0000 Uani D . . . . .
C12 C 0.8054(5) 0.72185(15) 0.7471(3) 0.0252 1.0000 Uani . . . . . .
C13 C 0.7755(5) 0.67998(15) 0.7170(3) 0.0256 1.0000 Uani . . . . . .
N14 N 0.6848(4) 0.65251(12) 0.7528(2) 0.0260 1.0000 Uani . . . . . .
C15 C 0.6213(5) 0.66491(16) 0.8182(3) 0.0289 1.0000 Uani . . . . . .
C16 C 0.6470(6) 0.70643(16) 0.8483(3) 0.0303 1.0000 Uani . . . . . .
C17 C 0.7394(5) 0.73563(15) 0.8135(3) 0.0257 1.0000 Uani . . . . . .
C18 C 0.6568(6) 0.60773(15) 0.7185(3) 0.0358 1.0000 Uani . . . . . .
O21 O -0.0625(4) 0.50281(12) 0.6614(2) 0.0359 1.0000 Uani D . . . . .
C22 C -0.0594(6) 0.52820(14) 0.5956(3) 0.0254 1.0000 Uani . . . . . .
C23 C 0.0979(5) 0.53720(14) 0.5821(3) 0.0231 1.0000 Uani . . . . . .
N24 N 0.1137(5) 0.56194(12) 0.5168(2) 0.0259 1.0000 Uani . . . . . .
C25 C -0.0207(6) 0.57869(15) 0.4629(3) 0.0311 1.0000 Uani . . . . . .
C26 C -0.1780(6) 0.57065(15) 0.4745(3) 0.0343 1.0000 Uani . . . . . .
C27 C -0.2000(6) 0.54516(15) 0.5407(3) 0.0294 1.0000 Uani . . . . . .
C28 C 0.2845(7) 0.57208(18) 0.5057(3) 0.0410 1.0000 Uani . . . . . .
O31 O 0.8431(5) 0.57925(13) 0.9138(3) 0.0446 1.0000 Uani D . . . . .
C32 C 0.8912(6) 0.53823(15) 0.9005(3) 0.0261 1.0000 Uani . . . . . .
C33 C 1.0334(6) 0.53455(15) 0.8684(3) 0.0274 1.0000 Uani . . . . . .
N34 N 1.0929(4) 0.49530(12) 0.8550(2) 0.0245 1.0000 Uani . . . . . .
C35 C 1.0178(6) 0.45858(15) 0.8710(3) 0.0296 1.0000 Uani . . . . . .
C36 C 0.8762(6) 0.46081(16) 0.9022(3) 0.0325 1.0000 Uani . . . . . .
C37 C 0.8094(5) 0.50083(15) 0.9171(3) 0.0262 1.0000 Uani . . . . . .
C38 C 1.2457(6) 0.49271(17) 0.8206(3) 0.0348 1.0000 Uani . . . . . .
O41 O 0.4150(5) 0.27396(12) 0.9525(2) 0.0419 1.0000 Uani D . . . . .
C42 C 0.5019(6) 0.28035(15) 0.8920(3) 0.0274 1.0000 Uani . . . . . .
C43 C 0.4953(6) 0.32191(15) 0.8597(3) 0.0277 1.0000 Uani . . . . . .
N44 N 0.5734(5) 0.33167(12) 0.7986(2) 0.0259 1.0000 Uani . . . . . .
C45 C 0.6615(6) 0.30144(17) 0.7686(3) 0.0331 1.0000 Uani . . . . . .
C46 C 0.6735(6) 0.25971(17) 0.7992(3) 0.0333 1.0000 Uani . . . . . .
C47 C 0.5922(6) 0.24890(15) 0.8621(3) 0.0275 1.0000 Uani . . . . . .
C48 C 0.5621(7) 0.37616(17) 0.7649(3) 0.0382 1.0000 Uani . . . . . .
I1 I 0.54379(4) 0.487516(10) 0.68240(2) 0.0287 1.0000 Uani . . . . . .
I2 I 0.17474(4) 0.624895(10) 0.719078(19) 0.0304 1.0000 Uani . . . . . .
I3 I 0.51249(4) 0.416235(11) 1.01170(2) 0.0326 1.0000 Uani . . . . . .
I4 I 0.46488(4) 0.326076(10) 0.53116(2) 0.0335 1.0000 Uani . . . . . .
I5 I 1.06552(4) 0.351909(10) 0.73719(2) 0.0349 1.0000 Uani . . . . . .
H31 H 0.1881 0.7715 0.9176 0.0338 1.0000 Uiso R . . . . .
H51 H -0.0864 0.7294 1.0672 0.0528 1.0000 Uiso R . . . . .
H61 H -0.0428 0.6572 1.0337 0.0558 1.0000 Uiso R . . . . .
H71 H 0.1114 0.6438 0.9335 0.0459 1.0000 Uiso R . . . . .
H82 H 0.0585 0.8033 1.0792 0.0762 1.0000 Uiso R . . . . .
H81 H 0.0916 0.8199 0.9944 0.0763 1.0000 Uiso R . . . . .
H83 H -0.0916 0.8090 1.0005 0.0759 1.0000 Uiso R . . . . .
H131 H 0.8174 0.6706 0.6721 0.0314 1.0000 Uiso R . . . . .
H151 H 0.5598 0.6447 0.8418 0.0349 1.0000 Uiso R . . . . .
H161 H 0.6012 0.7148 0.8934 0.0369 1.0000 Uiso R . . . . .
H171 H 0.7562 0.7638 0.8338 0.0312 1.0000 Uiso R . . . . .
H182 H 0.5835 0.5923 0.7460 0.0540 1.0000 Uiso R . . . . .
H183 H 0.7625 0.5928 0.7276 0.0538 1.0000 Uiso R . . . . .
H181 H 0.6079 0.6089 0.6594 0.0544 1.0000 Uiso R . . . . .
H231 H 0.1928 0.5262 0.6173 0.0280 1.0000 Uiso R . . . . .
H251 H -0.0050 0.5954 0.4182 0.0383 1.0000 Uiso R . . . . .
H261 H -0.2716 0.5824 0.4379 0.0422 1.0000 Uiso R . . . . .
H271 H -0.3074 0.5386 0.5488 0.0351 1.0000 Uiso R . . . . .
H283 H 0.2830 0.5724 0.4474 0.0624 1.0000 Uiso R . . . . .
H281 H 0.3187 0.5999 0.5297 0.0621 1.0000 Uiso R . . . . .
H282 H 0.3610 0.5502 0.5330 0.0622 1.0000 Uiso R . . . . .
H331 H 1.0878 0.5591 0.8561 0.0326 1.0000 Uiso R . . . . .
H351 H 1.0629 0.4325 0.8618 0.0356 1.0000 Uiso R . . . . .
H361 H 0.8246 0.4335 0.9145 0.0379 1.0000 Uiso R . . . . .
H371 H 0.7116 0.5025 0.9380 0.0310 1.0000 Uiso R . . . . .
H382 H 1.2260 0.4719 0.7757 0.0523 1.0000 Uiso R . . . . .
H381 H 1.3385 0.4834 0.8639 0.0520 1.0000 Uiso R . . . . .
H383 H 1.2688 0.5205 0.8004 0.0524 1.0000 Uiso R . . . . .
H431 H 0.4368 0.3434 0.8791 0.0328 1.0000 Uiso R . . . . .
H451 H 0.7141 0.3091 0.7265 0.0398 1.0000 Uiso R . . . . .
H461 H 0.7339 0.2389 0.7767 0.0411 1.0000 Uiso R . . . . .
H471 H 0.5994 0.2211 0.8834 0.0333 1.0000 Uiso R . . . . .
H483 H 0.6621 0.3831 0.7478 0.0574 1.0000 Uiso R . . . . .
H482 H 0.5470 0.3963 0.8073 0.0569 1.0000 Uiso R . . . . .
H481 H 0.4696 0.3780 0.7186 0.0572 1.0000 Uiso R . . . . .
H211 H -0.158(3) 0.500(2) 0.667(4) 0.0541 1.0000 Uiso D . . . . .
H311 H 0.764(6) 0.581(2) 0.937(4) 0.0673 1.0000 Uiso D . . . . .
H11 H 0.247(8) 0.6804(14) 0.830(4) 0.0724 1.0000 Uiso D . . . . .
H111 H 0.908(8) 0.7721(8) 0.724(4) 0.0568 1.0000 Uiso D . . . . .
H42 H 0.434(8) 0.2486(9) 0.967(4) 0.0630 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.5341(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.342(6) yes
O1 . H11 . 0.841(19) no
C2 . C3 . 1.378(7) yes
C2 . C7 . 1.379(7) yes
C3 . N4 . 1.330(6) yes
C3 . H31 . 0.919 no
N4 . C5 . 1.342(7) yes
N4 . C8 . 1.475(6) yes
C5 . C6 . 1.370(8) yes
C5 . H51 . 0.920 no
C6 . C7 . 1.374(7) yes
C6 . H61 . 0.965 no
C7 . H71 . 0.932 no
C8 . H82 . 0.955 no
C8 . H81 . 0.954 no
C8 . H83 . 0.956 no
O11 . C12 . 1.346(5) yes
O11 . H111 . 0.811(19) no
C12 . C13 . 1.379(6) yes
C12 . C17 . 1.388(6) yes
C13 . N14 . 1.343(6) yes
C13 . H131 . 0.926 no
N14 . C15 . 1.349(6) yes
N14 . C18 . 1.484(6) yes
C15 . C16 . 1.366(7) yes
C15 . H151 . 0.935 no
C16 . C17 . 1.378(6) yes
C16 . H161 . 0.939 no
C17 . H171 . 0.925 no
C18 . H182 . 0.954 no
C18 . H183 . 0.959 no
C18 . H181 . 0.960 no
O21 . C22 . 1.335(5) yes
O21 . H211 . 0.808(19) no
C22 . C23 . 1.381(6) yes
C22 . C27 . 1.388(6) yes
C23 . N24 . 1.343(5) yes
C23 . H231 . 0.919 no
N24 . C25 . 1.343(6) yes
N24 . C28 . 1.481(6) yes
C25 . C26 . 1.364(7) yes
C25 . H251 . 0.928 no
C26 . C27 . 1.383(7) yes
C26 . H261 . 0.930 no
C27 . H271 . 0.938 no
C28 . H283 . 0.953 no
C28 . H281 . 0.957 no
C28 . H282 . 0.957 no
O31 . C32 . 1.352(6) yes
O31 . H311 . 0.819(19) no
C32 . C33 . 1.386(6) yes
C32 . C37 . 1.387(6) yes
C33 . N34 . 1.337(6) yes
C33 . H331 . 0.922 no
N34 . C35 . 1.339(6) yes
N34 . C38 . 1.485(5) yes
C35 . C36 . 1.369(7) yes
C35 . H351 . 0.910 no
C36 . C37 . 1.389(7) yes
C36 . H361 . 0.980 no
C37 . H371 . 0.940 no
C38 . H382 . 0.960 no
C38 . H381 . 0.956 no
C38 . H383 . 0.949 no
O41 . C42 . 1.360(6) yes
O41 . H42 . 0.818(19) no
C42 . C43 . 1.379(6) yes
C42 . C47 . 1.372(6) yes
C43 . N44 . 1.339(6) yes
C43 . H431 . 0.914 no
N44 . C45 . 1.336(6) yes
N44 . C48 . 1.469(6) yes
C45 . C46 . 1.372(7) yes
C45 . H451 . 0.923 no
C46 . C47 . 1.390(7) yes
C46 . H461 . 0.934 no
C47 . H471 . 0.919 no
C48 . H483 . 0.947 no
C48 . H482 . 0.959 no
C48 . H481 . 0.942 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 . O1 . H11 . 115(5) no
O1 . C2 . C3 . 115.3(5) yes
O1 . C2 . C7 . 125.4(5) yes
C3 . C2 . C7 . 119.3(4) yes
C2 . C3 . N4 . 120.4(4) yes
C2 . C3 . H31 . 120.2 no
N4 . C3 . H31 . 119.4 no
C3 . N4 . C5 . 121.6(4) yes
C3 . N4 . C8 . 118.8(5) yes
C5 . N4 . C8 . 119.6(4) yes
N4 . C5 . C6 . 119.5(5) yes
N4 . C5 . H51 . 119.5 no
C6 . C5 . H51 . 121.0 no
C5 . C6 . C7 . 120.3(5) yes
C5 . C6 . H61 . 120.3 no
C7 . C6 . H61 . 119.3 no
C2 . C7 . C6 . 118.9(5) yes
C2 . C7 . H71 . 120.2 no
C6 . C7 . H71 . 120.9 no
N4 . C8 . H82 . 108.5 no
N4 . C8 . H81 . 108.8 no
H82 . C8 . H81 . 109.8 no
N4 . C8 . H83 . 109.5 no
H82 . C8 . H83 . 110.8 no
H81 . C8 . H83 . 109.4 no
C12 . O11 . H111 . 115(4) no
O11 . C12 . C13 . 116.1(4) yes
O11 . C12 . C17 . 124.2(4) yes
C13 . C12 . C17 . 119.7(4) yes
C12 . C13 . N14 . 120.0(4) yes
C12 . C13 . H131 . 120.3 no
N14 . C13 . H131 . 119.6 no
C13 . N14 . C15 . 121.4(4) yes
C13 . N14 . C18 . 118.0(4) yes
C15 . N14 . C18 . 120.6(4) yes
N14 . C15 . C16 . 119.6(4) yes
N14 . C15 . H151 . 118.9 no
C16 . C15 . H151 . 121.5 no
C15 . C16 . C17 . 120.8(4) yes
C15 . C16 . H161 . 118.9 no
C17 . C16 . H161 . 120.3 no
C12 . C17 . C16 . 118.4(4) yes
C12 . C17 . H171 . 121.1 no
C16 . C17 . H171 . 120.6 no
N14 . C18 . H182 . 109.9 no
N14 . C18 . H183 . 109.3 no
H182 . C18 . H183 . 109.2 no
N14 . C18 . H181 . 109.8 no
H182 . C18 . H181 . 109.5 no
H183 . C18 . H181 . 109.0 no
C22 . O21 . H211 . 110(4) no
O21 . C22 . C23 . 116.0(4) yes
O21 . C22 . C27 . 125.2(4) yes
C23 . C22 . C27 . 118.8(4) yes
C22 . C23 . N24 . 120.4(4) yes
C22 . C23 . H231 . 120.4 no
N24 . C23 . H231 . 119.2 no
C23 . N24 . C25 . 121.7(4) yes
C23 . N24 . C28 . 118.9(4) yes
C25 . N24 . C28 . 119.3(4) yes
N24 . C25 . C26 . 119.6(4) yes
N24 . C25 . H251 . 119.3 no
C26 . C25 . H251 . 121.1 no
C25 . C26 . C27 . 120.5(4) yes
C25 . C26 . H261 . 120.1 no
C27 . C26 . H261 . 119.3 no
C22 . C27 . C26 . 119.0(4) yes
C22 . C27 . H271 . 119.3 no
C26 . C27 . H271 . 121.8 no
N24 . C28 . H283 . 109.3 no
N24 . C28 . H281 . 109.4 no
H283 . C28 . H281 . 109.8 no
N24 . C28 . H282 . 109.1 no
H283 . C28 . H282 . 109.5 no
H281 . C28 . H282 . 109.8 no
C32 . O31 . H311 . 115(5) no
O31 . C32 . C33 . 115.9(4) yes
O31 . C32 . C37 . 124.7(4) yes
C33 . C32 . C37 . 119.4(4) yes
C32 . C33 . N34 . 120.3(4) yes
C32 . C33 . H331 . 120.3 no
N34 . C33 . H331 . 119.4 no
C33 . N34 . C35 . 121.8(4) yes
C33 . N34 . C38 . 118.7(4) yes
C35 . N34 . C38 . 119.5(4) yes
N34 . C35 . C36 . 119.7(4) yes
N34 . C35 . H351 . 119.2 no
C36 . C35 . H351 . 121.1 no
C35 . C36 . C37 . 120.6(4) yes
C35 . C36 . H361 . 118.2 no
C37 . C36 . H361 . 121.1 no
C36 . C37 . C32 . 118.2(4) yes
C36 . C37 . H371 . 120.9 no
C32 . C37 . H371 . 120.9 no
N34 . C38 . H382 . 108.6 no
N34 . C38 . H381 . 109.0 no
H382 . C38 . H381 . 109.5 no
N34 . C38 . H383 . 109.6 no
H382 . C38 . H383 . 110.1 no
H381 . C38 . H383 . 109.9 no
C42 . O41 . H42 . 105(5) no
O41 . C42 . C43 . 115.7(4) yes
O41 . C42 . C47 . 124.9(4) yes
C43 . C42 . C47 . 119.4(4) yes
C42 . C43 . N44 . 120.8(4) yes
C42 . C43 . H431 . 120.7 no
N44 . C43 . H431 . 118.5 no
C43 . N44 . C45 . 120.6(4) yes
C43 . N44 . C48 . 119.3(4) yes
C45 . N44 . C48 . 120.1(4) yes
N44 . C45 . C46 . 120.9(4) yes
N44 . C45 . H451 . 118.8 no
C46 . C45 . H451 . 120.3 no
C45 . C46 . C47 . 119.3(5) yes
C45 . C46 . H461 . 119.7 no
C47 . C46 . H461 . 121.0 no
C46 . C47 . C42 . 119.0(4) yes
C46 . C47 . H471 . 120.3 no
C42 . C47 . H471 . 120.7 no
N44 . C48 . H483 . 109.7 no
N44 . C48 . H482 . 109.6 no
H483 . C48 . H482 . 109.4 no
N44 . C48 . H481 . 109.3 no
H483 . C48 . H481 . 109.5 no
H482 . C48 . H481 . 109.4 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C5 . H51 . O11 3_465 148.57(15) 0.920 2.461 3.281(7) yes
C16 . H161 . O41 2_667 157.98(13) 0.939 2.583 3.471(7) yes
C46 . H461 . O1 4_646 140.15(14) 0.934 2.510 3.282(7) yes



# 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
-1 0 20 x .
-7 0 16 x .
0 4 19 x .
-7 1 17 x .
####################################################################### 
# 
# 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_1BPh4
_database_code_depnum_ccdc_archive 'CCDC 2050537'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;
#==============================================================================
# start Validation Reply Form
_vrf_PLAT027_1BPh4               
;
PROBLEM: _diffrn_reflns_theta_full (too) Low ............      25.04 Degree
RESPONSE: Crystals were very large and polycrystalline. Cutting with a scalpel 
gave an approximately single crystal, although diffraction was weak at high 
angle (even using Cu radiation and long exposure times) and crystals still 
appeared to be somewhat split/polycrystalline. Despite several attempts, it 
was not possible to obtain better quality crystals.
;

_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          
; 
Crystals were very large and polycrystalline. Cutting with a scalpel gave an
approximately single crystal, although diffraction was weak at high angle
(even using Cu radiation and long exposure times) and crystals still appeared
to be somewhat split/polycrystalline. Despite several attempts, it was not 
possible to obtain better quality crystals.

The data generally refined smoothly, despite the low data quality and the only
restraints necessary were soft restraints on thermal and vibrational ellipsoid
parameters.

Due to the low data quality, hydrogen atoms are inserted at geometric 
positions.
;

_cell_length_a                   16.154(2)
_cell_length_b                   10.0700(15)
_cell_length_c                   14.0816(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.992(11)
_cell_angle_gamma                90
_cell_volume                     2289.3(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/m '
_symmetry_space_group_name_Hall  '-C 2y'

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0090 0.0039 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

_chemical_formula_sum            'C30 H28 B1 N1 O1'
_chemical_formula_moiety         'C30 H28 B1 N1 O1'
_chemical_compound_source        synthesized
_chemical_formula_weight         429.37


_cell_measurement_reflns_used    10086
_cell_measurement_theta_min      3
_cell_measurement_theta_max      72
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_min          0.060
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_max          0.160

_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.565

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_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            17202
_reflns_number_total             2302
_diffrn_reflns_av_R_equivalents  0.089

_diffrn_reflns_theta_min         3.140
_diffrn_reflns_theta_max         73.657
_diffrn_measured_fraction_theta_max 0.940

_diffrn_reflns_theta_full        25.043
_diffrn_measured_fraction_theta_full 0.984

_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -19
_reflns_limit_h_max              19
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   2.89
_oxford_diffrn_Wilson_scale      0.06

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.50
_refine_diff_density_max         0.86

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         2073
_refine_ls_number_restraints     214
_refine_ls_number_parameters     177
_oxford_refine_ls_R_factor_ref   0.1626
_refine_ls_wR_factor_ref         0.2956
_refine_ls_goodness_of_fit_ref   1.0465
_refine_ls_shift/su_max          0.0008549
_refine_ls_shift/su_mean         0.0000105

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2073
_refine_ls_R_factor_all          0.1626
_refine_ls_wR_factor_all         0.2956

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1802
_refine_ls_R_factor_gt           0.1524
_refine_ls_wR_factor_gt          0.2933

_chemical_absolute_configuration .

_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, 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: 
 0.391E+04 0.577E+04 0.322E+04 0.113E+04 
;

# 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
O1 O 0.4375(4) 0.000000(7) 0.4316(4) 0.0625 1.0000 Uani S TU . . . .
C2 C 0.3795(5) 0.0000 0.3602(6) 0.0462 1.0000 Uani S TU . . . .
C3 C 0.4008(5) 0.000000(7) 0.2679(6) 0.0417 1.0000 Uani S TU . . . .
N4 N 0.3407(4) 0.0000 0.1992(5) 0.0392 1.0000 Uani S TU . . . .
C5 C 0.2603(5) 0.000000(7) 0.2188(6) 0.0486 1.0000 Uani S TU . . . .
C6 C 0.2369(6) 0.000000(7) 0.3092(7) 0.0601 1.0000 Uani S TU . . . .
C7 C 0.2959(6) 0.000000(7) 0.3842(6) 0.0524 1.0000 Uani S TU . . . .
C8 C 0.3663(6) 0.000000(7) 0.0976(7) 0.0507 1.0000 Uani S TU . . . .
B10 B 0.6812(6) 0.0000 0.2434(7) 0.0373 1.0000 Uani S TU . . . .
C11 C 0.6177(3) 0.1258(8) 0.2452(4) 0.0411 1.0000 Uani . U . . . .
C12 C 0.5801(4) 0.1756(9) 0.1605(5) 0.0492 1.0000 Uani . U . . . .
C13 C 0.5171(4) 0.2697(11) 0.1613(8) 0.0746 1.0000 Uani . U . . . .
C14 C 0.4889(5) 0.3147(9) 0.2461(8) 0.0743 1.0000 Uani . U . . . .
C15 C 0.5247(4) 0.2703(11) 0.3312(8) 0.0746 1.0000 Uani . U . . . .
C16 C 0.5873(4) 0.1761(9) 0.3297(5) 0.0489 1.0000 Uani . U . . . .
C21 C 0.7410(5) 0.0000 0.1508(6) 0.0350 1.0000 Uani S TU . . . .
C22 C 0.7715(3) 0.1160(8) 0.1135(4) 0.0373 1.0000 Uani . U . . . .
C23 C 0.8281(3) 0.1182(8) 0.0395(4) 0.0360 1.0000 Uani . U . . . .
C24 C 0.8560(6) 0.000000(7) 0.0050(7) 0.0418 1.0000 Uani S TU . . . .
C31 C 0.7472(5) 0.0000 0.3370(6) 0.0357 1.0000 Uani S TU . . . .
C32 C 0.7805(4) 0.1178(9) 0.3731(4) 0.0442 1.0000 Uani . U . . . .
C33 C 0.8423(4) 0.1176(10) 0.4462(4) 0.0497 1.0000 Uani . U . . . .
C34 C 0.8736(5) 0.000000(7) 0.4802(7) 0.0511 1.0000 Uani S TU . . . .
H81 H 0.3196 0.0000 0.0548 0.0683 1.0000 Uiso RS . . . . .
H82 H 0.3994 0.0870 0.0849 0.0683 1.0000 Uiso R . . . . .
H31 H 0.4574 0.0000 0.2519 0.0517 1.0000 Uiso RS . . . . .
H51 H 0.2195 0.0000 0.1685 0.0590 1.0000 Uiso RS . . . . .
H121 H 0.5985 0.1427 0.1016 0.0673 1.0000 Uiso R . . . . .
H131 H 0.4945 0.3035 0.1031 0.0930 1.0000 Uiso R . . . . .
H141 H 0.4438 0.3752 0.2468 0.1002 1.0000 Uiso R . . . . .
H151 H 0.5073 0.3050 0.3900 0.0932 1.0000 Uiso R . . . . .
H161 H 0.6105 0.1436 0.3881 0.0647 1.0000 Uiso R . . . . .
H221 H 0.7538 0.1977 0.1396 0.0526 1.0000 Uiso R . . . . .
H231 H 0.8458 0.1995 0.0127 0.0508 1.0000 Uiso R . . . . .
H241 H 0.8967 0.0000 -0.0421 0.0564 1.0000 Uiso RS . . . . .
H321 H 0.7648 0.1997 0.3442 0.0596 1.0000 Uiso R . . . . .
H331 H 0.8565 0.2069 0.4612 0.0645 1.0000 Uiso R . . . . .
H341 H 0.9176 0.0000 0.5267 0.0654 1.0000 Uiso RS . . . . .
H61 H 0.1798 0.0000 0.3230 0.0739 1.0000 Uiso RS . . . . .
H71 H 0.2806 0.0000 0.4487 0.0641 1.0000 Uiso RS . . . . .
H11 H 0.4204 0.0000 0.4954 0.0756 1.0000 Uiso RS . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.7(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
O1 . C2 . 1.350(10) yes
O1 . H11 . 0.950 no
C2 . C3 . 1.356(12) yes
C2 . C7 . 1.403(13) yes
C3 . N4 . 1.346(10) yes
C3 . H31 . 0.950 no
N4 . C5 . 1.337(11) yes
N4 . C8 . 1.503(11) yes
C5 . C6 . 1.340(13) yes
C5 . H51 . 0.950 no
C6 . C7 . 1.397(12) yes
C6 . H61 . 0.950 no
C7 . H71 . 0.950 no
C8 . H82 5_555 1.045 no
C8 . H81 . 0.950 no
C8 . H82 . 1.045 no
B10 . C11 5_555 1.630(9) yes
B10 . C11 . 1.630(9) yes
B10 . C21 . 1.649(13) yes
B10 . C31 . 1.666(12) yes
C11 . C12 . 1.412(9) yes
C11 . C16 . 1.398(9) yes
C12 . C13 . 1.391(11) yes
C12 . H121 . 0.950 no
C13 . C14 . 1.370(14) yes
C13 . H131 . 0.950 no
C14 . C15 . 1.385(13) yes
C14 . H141 . 0.950 no
C15 . C16 . 1.387(11) yes
C15 . H151 . 0.950 no
C16 . H161 . 0.950 no
C21 . C22 5_555 1.379(8) yes
C21 . C22 . 1.379(8) yes
C22 . C23 . 1.409(8) yes
C22 . H221 . 0.950 no
C23 . C24 . 1.368(9) yes
C23 . H231 . 0.950 no
C24 . H241 . 0.950 no
C31 . C32 5_555 1.391(9) yes
C31 . C32 . 1.391(9) yes
C32 . C33 . 1.409(8) yes
C32 . H321 . 0.950 no
C33 . C34 . 1.368(10) yes
C33 . H331 . 0.950 no
C34 . H341 . 0.950 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . H11 . 119.2 no
O1 . C2 . C3 . 121.4(8) yes
O1 . C2 . C7 . 118.0(8) yes
C3 . C2 . C7 . 120.7(8) yes
C2 . C3 . N4 . 119.2(8) yes
C2 . C3 . H31 . 120.4 no
N4 . C3 . H31 . 120.4 no
C3 . N4 . C5 . 122.2(8) yes
C3 . N4 . C8 . 117.9(7) yes
C5 . N4 . C8 . 119.9(7) yes
N4 . C5 . C6 . 120.3(8) yes
N4 . C5 . H51 . 119.9 no
C6 . C5 . H51 . 119.8 no
C5 . C6 . C7 . 120.7(9) yes
C5 . C6 . H61 . 120.1 no
C7 . C6 . H61 . 119.1 no
C2 . C7 . C6 . 117.0(9) yes
C2 . C7 . H71 . 121.0 no
C6 . C7 . H71 . 122.0 no
N4 . C8 . H82 5_555 108.8 no
N4 . C8 . H81 . 111.3 no
H82 5_555 C8 . H81 . 107.0 no
N4 . C8 . H82 . 108.8 no
H82 5_555 C8 . H82 . 113.9 no
H81 . C8 . H82 . 107.0 no
C11 5_555 B10 . C11 . 102.0(7) yes
C11 5_555 B10 . C21 . 113.5(5) yes
C11 . B10 . C21 . 113.5(5) yes
C11 5_555 B10 . C31 . 111.9(5) yes
C11 . B10 . C31 . 111.9(5) yes
C21 . B10 . C31 . 104.4(7) yes
B10 . C11 . C12 . 121.0(7) yes
B10 . C11 . C16 . 122.4(7) yes
C12 . C11 . C16 . 115.9(7) yes
C11 . C12 . C13 . 121.9(8) yes
C11 . C12 . H121 . 118.4 no
C13 . C12 . H121 . 119.7 no
C12 . C13 . C14 . 119.9(8) yes
C12 . C13 . H131 . 119.8 no
C14 . C13 . H131 . 120.3 no
C13 . C14 . C15 . 120.4(8) yes
C13 . C14 . H141 . 120.0 no
C15 . C14 . H141 . 119.7 no
C14 . C15 . C16 . 119.3(9) yes
C14 . C15 . H151 . 120.6 no
C16 . C15 . H151 . 120.1 no
C11 . C16 . C15 . 122.6(8) yes
C11 . C16 . H161 . 118.1 no
C15 . C16 . H161 . 119.3 no
B10 . C21 . C22 5_555 121.9(4) yes
B10 . C21 . C22 . 121.9(4) yes
C22 5_555 C21 . C22 . 115.7(8) yes
C21 . C22 . C23 . 123.0(7) yes
C21 . C22 . H221 . 118.0 no
C23 . C22 . H221 . 119.0 no
C22 . C23 . C24 . 118.6(7) yes
C22 . C23 . H231 . 121.3 no
C24 . C23 . H231 . 120.1 no
C23 . C24 . C23 5_555 120.9(9) yes
C23 . C24 . H241 . 119.5 no
C23 5_555 C24 . H241 . 119.5 no
B10 . C31 . C32 5_555 121.2(4) yes
B10 . C31 . C32 . 121.2(4) yes
C32 5_555 C31 . C32 . 117.0(8) yes
C31 . C32 . C33 . 121.4(8) yes
C31 . C32 . H321 . 119.3 no
C33 . C32 . H321 . 119.1 no
C32 . C33 . C34 . 120.1(8) yes
C32 . C33 . H331 . 108.7 no
C34 . C33 . H331 . 131.2 no
C33 . C34 . C33 5_555 120.0(9) yes
C33 . C34 . H341 . 120.0 no
C33 5_555 C34 . H341 . 120.0 no



# 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
2 2 0 x .
1 1 12 x .
15 1 5 x .
-1 1 13 x .
5 3 0 x .
####################################################################### 
# 
# 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_3PF6_acetone
_database_code_depnum_ccdc_archive 'CCDC 2050541'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
The asymmetric unit cell contains the bis-quinolinium dication, two PF6 
anions and one acetone solvate.

C-H hydrogen atoms were generally visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. O-H hydrogen 
atoms were visible in the Fourier difference map and were refined
with restraints on bond lengths and angles. 

Other than this, it was not necessary to use any crystallographic restraints.
;

_cell_length_a                   10.4429(2)
_cell_length_b                   11.3851(3)
_cell_length_c                   13.3448(3)
_cell_angle_alpha                78.042(2)
_cell_angle_beta                 78.837(2)
_cell_angle_gamma                83.599(2)
_cell_volume                     1518.60(3)

_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 0.0181 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'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

_chemical_formula_sum            'C29 H28 F12 N2 O3 P2'
_chemical_formula_moiety         'C26 H22 N2 O2, 2(F6 P), C3 H6 O'
_chemical_compound_source        synthesized
_chemical_formula_weight         742.47


_cell_measurement_reflns_used    10147
_cell_measurement_theta_min      3
_cell_measurement_theta_max      72
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_max          0.360

_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             755.997
_exptl_absorpt_coefficient_mu    2.320

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_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            29783
_reflns_number_total             5971
_diffrn_reflns_av_R_equivalents  0.035

_diffrn_reflns_theta_min         3.439
_diffrn_reflns_theta_max         72.344
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        72.344
_diffrn_measured_fraction_theta_full 0.996

_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              -13
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   3.15
_oxford_diffrn_Wilson_scale      0.08

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.66
_refine_diff_density_max         0.80

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         5348
_refine_ls_number_restraints     2
_refine_ls_number_parameters     439
_oxford_refine_ls_R_factor_ref   0.0610
_refine_ls_wR_factor_ref         0.1548
_refine_ls_goodness_of_fit_ref   0.9706
_refine_ls_shift/su_max          0.0006281
_refine_ls_shift/su_mean         0.0000348

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5348
_refine_ls_R_factor_all          0.0610
_refine_ls_wR_factor_all         0.1548

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4905
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_gt          0.1519

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    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: 
 0.200E+04 0.335E+04 0.204E+04 824. 173. 
;

# 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
O1 O 0.63522(17) 0.50417(17) 0.58949(15) 0.0354 1.0000 Uani D . . . . .
C2 C 0.5456(2) 0.4221(2) 0.60943(18) 0.0292 1.0000 Uani . . . . . .
C3 C 0.5729(3) 0.3157(2) 0.5728(2) 0.0332 1.0000 Uani . . . . . .
C4 C 0.4805(3) 0.2292(2) 0.5930(2) 0.0381 1.0000 Uani . . . . . .
C5 C 0.3609(3) 0.2475(2) 0.6514(2) 0.0367 1.0000 Uani . . . . . .
C6 C 0.3291(3) 0.3546(2) 0.69217(19) 0.0321 1.0000 Uani . . . . . .
C7 C 0.4197(2) 0.4448(2) 0.67033(18) 0.0270 1.0000 Uani . . . . . .
C8 C 0.2071(3) 0.3721(3) 0.7569(2) 0.0392 1.0000 Uani . . . . . .
C9 C 0.1757(3) 0.4749(3) 0.7965(2) 0.0426 1.0000 Uani . . . . . .
C10 C 0.2644(3) 0.5621(3) 0.7713(2) 0.0369 1.0000 Uani . . . . . .
N11 N 0.3817(2) 0.54926(19) 0.71083(16) 0.0299 1.0000 Uani . . . . . .
C12 C 0.4677(2) 0.6489(2) 0.69808(19) 0.0297 1.0000 Uani . . . . . .
C13 C 0.5594(2) 0.6238(2) 0.77618(19) 0.0291 1.0000 Uani . . . . . .
C14 C 0.5685(3) 0.5127(2) 0.8431(2) 0.0392 1.0000 Uani . . . . . .
C15 C 0.6552(3) 0.4898(2) 0.9127(2) 0.0435 1.0000 Uani . . . . . .
C16 C 0.7331(3) 0.5780(3) 0.9163(2) 0.0381 1.0000 Uani . . . . . .
C17 C 0.7230(3) 0.6890(2) 0.8520(2) 0.0332 1.0000 Uani . . . . . .
C18 C 0.6368(2) 0.7139(2) 0.78192(18) 0.0276 1.0000 Uani . . . . . .
C19 C 0.6313(3) 0.8358(2) 0.70837(19) 0.0322 1.0000 Uani . . . . . .
N20 N 0.6658(2) 0.93393(19) 0.75477(17) 0.0329 1.0000 Uani . . . . . .
C21 C 0.7942(3) 0.9536(3) 0.7350(2) 0.0380 1.0000 Uani . . . . . .
C22 C 0.8393(3) 1.0434(3) 0.7741(3) 0.0499 1.0000 Uani . . . . . .
C23 C 0.7540(3) 1.1141(3) 0.8270(3) 0.0470 1.0000 Uani . . . . . .
C24 C 0.5752(2) 1.0013(2) 0.81371(18) 0.0273 1.0000 Uani . . . . . .
C25 C 0.6163(3) 1.0973(2) 0.8484(2) 0.0385 1.0000 Uani . . . . . .
C26 C 0.5279(4) 1.1718(3) 0.9041(2) 0.0470 1.0000 Uani . . . . . .
C27 C 0.3975(3) 1.1506(3) 0.9259(2) 0.0476 1.0000 Uani . . . . . .
C28 C 0.3538(3) 1.0541(3) 0.8962(2) 0.0416 1.0000 Uani . . . . . .
C29 C 0.4383(3) 0.9770(2) 0.8434(2) 0.0333 1.0000 Uani . . . . . .
O30 O 0.39800(18) 0.8794(2) 0.82175(18) 0.0444 1.0000 Uani D . . . . .
P101 P 0.04366(7) 0.76788(7) 0.96778(6) 0.0388 1.0000 Uani . . . . . .
F102 F 0.0538(3) 0.7521(4) 1.08578(18) 0.1091 1.0000 Uani . . . . . .
F103 F 0.0706(4) 0.9032(3) 0.9478(3) 0.1225 1.0000 Uani . . . . . .
F104 F 0.19787(18) 0.7398(2) 0.93832(18) 0.0730 1.0000 Uani . . . . . .
F105 F 0.0252(3) 0.6296(2) 0.9819(2) 0.0819 1.0000 Uani . . . . . .
F106 F -0.1084(2) 0.7933(3) 0.9959(3) 0.1102 1.0000 Uani . . . . . .
F107 F 0.0341(2) 0.7779(2) 0.84832(16) 0.0683 1.0000 Uani . . . . . .
P111 P 0.21056(6) 0.95395(6) 0.58420(5) 0.0315 1.0000 Uani . . . . . .
F112 F 0.18476(17) 0.99050(19) 0.69591(13) 0.0501 1.0000 Uani . . . . . .
F113 F 0.1973(2) 1.09286(16) 0.53076(15) 0.0563 1.0000 Uani . . . . . .
F114 F 0.36435(15) 0.96024(19) 0.57643(15) 0.0541 1.0000 Uani . . . . . .
F115 F 0.22528(19) 0.81441(16) 0.63573(16) 0.0569 1.0000 Uani . . . . . .
F116 F 0.05786(16) 0.94516(18) 0.59300(15) 0.0524 1.0000 Uani . . . . . .
F117 F 0.23718(18) 0.91871(16) 0.47103(14) 0.0489 1.0000 Uani . . . . . .
O201 O 1.1427(2) 0.54628(19) 0.53776(16) 0.0460 1.0000 Uani . . . . . .
C202 C 1.0537(4) 0.7056(3) 0.4229(3) 0.0584 1.0000 Uani . . . . . .
C203 C 1.0556(3) 0.6252(3) 0.5252(2) 0.0409 1.0000 Uani . . . . . .
C204 C 0.9485(3) 0.6451(3) 0.6125(3) 0.0595 1.0000 Uani . . . . . .
H31 H 0.6571 0.3019 0.5335 0.0398 1.0000 Uiso R . . . . .
H41 H 0.5021 0.1573 0.5657 0.0440 1.0000 Uiso R . . . . .
H51 H 0.2981 0.1910 0.6661 0.0441 1.0000 Uiso R . . . . .
H81 H 0.1471 0.3121 0.7720 0.0449 1.0000 Uiso R . . . . .
H91 H 0.0940 0.4882 0.8403 0.0504 1.0000 Uiso R . . . . .
H101 H 0.2432 0.6350 0.7966 0.0453 1.0000 Uiso R . . . . .
H121 H 0.5188 0.6619 0.6272 0.0361 1.0000 Uiso R . . . . .
H122 H 0.4094 0.7207 0.7093 0.0358 1.0000 Uiso R . . . . .
H141 H 0.5175 0.4527 0.8397 0.0475 1.0000 Uiso R . . . . .
H151 H 0.6621 0.4126 0.9580 0.0521 1.0000 Uiso R . . . . .
H161 H 0.7922 0.5627 0.9630 0.0460 1.0000 Uiso R . . . . .
H171 H 0.7753 0.7482 0.8570 0.0393 1.0000 Uiso R . . . . .
H192 H 0.6949 0.8323 0.6460 0.0387 1.0000 Uiso R . . . . .
H191 H 0.5458 0.8550 0.6898 0.0367 1.0000 Uiso R . . . . .
H211 H 0.8520 0.9065 0.6953 0.0472 1.0000 Uiso R . . . . .
H221 H 0.9299 1.0535 0.7637 0.0607 1.0000 Uiso R . . . . .
H231 H 0.7772 1.1784 0.8511 0.0546 1.0000 Uiso R . . . . .
H261 H 0.5587 1.2354 0.9247 0.0560 1.0000 Uiso R . . . . .
H271 H 0.3338 1.2009 0.9625 0.0556 1.0000 Uiso R . . . . .
H281 H 0.2655 1.0399 0.9131 0.0501 1.0000 Uiso R . . . . .
H2021 H 0.9712 0.7048 0.4027 0.0877 1.0000 Uiso R . . . . .
H2023 H 1.1197 0.6797 0.3703 0.0878 1.0000 Uiso R . . . . .
H2022 H 1.0661 0.7865 0.4275 0.0882 1.0000 Uiso R . . . . .
H2041 H 0.8663 0.6576 0.5887 0.0902 1.0000 Uiso R . . . . .
H2043 H 0.9470 0.5750 0.6676 0.0899 1.0000 Uiso R . . . . .
H2042 H 0.9623 0.7133 0.6385 0.0900 1.0000 Uiso R . . . . .
H11 H 0.705(2) 0.484(3) 0.553(3) 0.0537 1.0000 Uiso D . . . . .
H301 H 0.321(2) 0.868(4) 0.840(3) 0.0659 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.64(5)
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 . C2 . 1.347(3) yes
O1 . H11 . 0.828(18) no
C2 . C3 . 1.379(4) yes
C2 . C7 . 1.433(3) yes
C3 . C4 . 1.405(4) yes
C3 . H31 . 0.948 no
C4 . C5 . 1.357(4) yes
C4 . H41 . 0.950 no
C5 . C6 . 1.417(4) yes
C5 . H51 . 0.935 no
C6 . C7 . 1.421(4) yes
C6 . C8 . 1.413(4) yes
C7 . N11 . 1.393(3) yes
C8 . C9 . 1.363(4) yes
C8 . H81 . 0.943 no
C9 . C10 . 1.380(4) yes
C9 . H91 . 0.952 no
C10 . N11 . 1.341(3) yes
C10 . H101 . 0.948 no
N11 . C12 . 1.486(3) yes
C12 . C13 . 1.512(3) yes
C12 . H121 . 0.983 no
C12 . H122 . 0.982 no
C13 . C14 . 1.394(4) yes
C13 . C18 . 1.398(4) yes
C14 . C15 . 1.387(4) yes
C14 . H141 . 0.926 no
C15 . C16 . 1.375(4) yes
C15 . H151 . 0.962 no
C16 . C17 . 1.380(4) yes
C16 . H161 . 0.938 no
C17 . C18 . 1.387(4) yes
C17 . H171 . 0.934 no
C18 . C19 . 1.527(3) yes
C19 . N20 . 1.492(3) yes
C19 . H192 . 0.964 no
C19 . H191 . 0.963 no
N20 . C21 . 1.350(3) yes
N20 . C24 . 1.379(3) yes
C21 . C22 . 1.401(4) yes
C21 . H211 . 0.924 no
C22 . C23 . 1.332(5) yes
C22 . H221 . 0.946 no
C23 . C25 . 1.437(4) yes
C23 . H231 . 0.929 no
C24 . C25 . 1.410(4) yes
C24 . C29 . 1.449(3) yes
C25 . C26 . 1.394(4) yes
C26 . C27 . 1.375(5) yes
C26 . H261 . 0.934 no
C27 . C28 . 1.390(5) yes
C27 . H271 . 0.956 no
C28 . C29 . 1.375(4) yes
C28 . H281 . 0.930 no
C29 . O30 . 1.334(3) yes
O30 . H301 . 0.813(18) no
P101 . F102 . 1.570(2) yes
P101 . F103 . 1.556(3) yes
P101 . F104 . 1.594(2) yes
P101 . F105 . 1.576(2) yes
P101 . F106 . 1.568(2) yes
P101 . F107 . 1.596(2) yes
P111 . F112 . 1.5951(18) yes
P111 . F113 . 1.5972(18) yes
P111 . F114 . 1.5979(16) yes
P111 . F115 . 1.5982(18) yes
P111 . F116 . 1.5890(16) yes
P111 . F117 . 1.6071(18) yes
O201 . C203 . 1.216(4) yes
C202 . C203 . 1.480(5) yes
C202 . H2021 . 0.953 no
C202 . H2023 . 0.953 no
C202 . H2022 . 0.960 no
C203 . C204 . 1.485(4) yes
C204 . H2041 . 0.958 no
C204 . H2043 . 0.966 no
C204 . H2042 . 0.949 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 . O1 . H11 . 113(3) no
O1 . C2 . C3 . 121.2(2) yes
O1 . C2 . C7 . 119.7(2) yes
C3 . C2 . C7 . 119.1(2) yes
C2 . C3 . C4 . 121.9(2) yes
C2 . C3 . H31 . 117.8 no
C4 . C3 . H31 . 120.4 no
C3 . C4 . C5 . 120.4(3) yes
C3 . C4 . H41 . 119.7 no
C5 . C4 . H41 . 119.9 no
C4 . C5 . C6 . 119.7(3) yes
C4 . C5 . H51 . 121.9 no
C6 . C5 . H51 . 118.4 no
C5 . C6 . C7 . 120.8(2) yes
C5 . C6 . C8 . 120.1(2) yes
C7 . C6 . C8 . 119.0(2) yes
C2 . C7 . C6 . 118.0(2) yes
C2 . C7 . N11 . 123.9(2) yes
C6 . C7 . N11 . 118.1(2) yes
C6 . C8 . C9 . 120.6(3) yes
C6 . C8 . H81 . 119.3 no
C9 . C8 . H81 . 120.2 no
C8 . C9 . C10 . 118.8(3) yes
C8 . C9 . H91 . 121.8 no
C10 . C9 . H91 . 119.4 no
C9 . C10 . N11 . 122.8(3) yes
C9 . C10 . H101 . 120.0 no
N11 . C10 . H101 . 117.2 no
C7 . N11 . C10 . 120.6(2) yes
C7 . N11 . C12 . 124.1(2) yes
C10 . N11 . C12 . 115.1(2) yes
N11 . C12 . C13 . 112.3(2) yes
N11 . C12 . H121 . 109.2 no
C13 . C12 . H121 . 109.6 no
N11 . C12 . H122 . 106.5 no
C13 . C12 . H122 . 108.9 no
H121 . C12 . H122 . 110.3 no
C12 . C13 . C14 . 121.6(2) yes
C12 . C13 . C18 . 119.4(2) yes
C14 . C13 . C18 . 119.0(2) yes
C13 . C14 . C15 . 121.1(3) yes
C13 . C14 . H141 . 119.4 no
C15 . C14 . H141 . 119.5 no
C14 . C15 . C16 . 119.6(2) yes
C14 . C15 . H151 . 120.8 no
C16 . C15 . H151 . 119.6 no
C15 . C16 . C17 . 119.8(2) yes
C15 . C16 . H161 . 119.9 no
C17 . C16 . H161 . 120.3 no
C16 . C17 . C18 . 121.5(2) yes
C16 . C17 . H171 . 118.3 no
C18 . C17 . H171 . 120.2 no
C13 . C18 . C17 . 119.0(2) yes
C13 . C18 . C19 . 120.4(2) yes
C17 . C18 . C19 . 120.6(2) yes
C18 . C19 . N20 . 111.8(2) yes
C18 . C19 . H192 . 109.0 no
N20 . C19 . H192 . 106.8 no
C18 . C19 . H191 . 110.6 no
N20 . C19 . H191 . 109.8 no
H192 . C19 . H191 . 108.8 no
C19 . N20 . C21 . 115.2(2) yes
C19 . N20 . C24 . 123.6(2) yes
C21 . N20 . C24 . 121.3(2) yes
N20 . C21 . C22 . 120.7(3) yes
N20 . C21 . H211 . 118.8 no
C22 . C21 . H211 . 120.5 no
C21 . C22 . C23 . 119.8(3) yes
C21 . C22 . H221 . 120.4 no
C23 . C22 . H221 . 119.9 no
C22 . C23 . C25 . 121.2(3) yes
C22 . C23 . H231 . 123.8 no
C25 . C23 . H231 . 115.0 no
N20 . C24 . C25 . 119.2(2) yes
N20 . C24 . C29 . 123.0(2) yes
C25 . C24 . C29 . 117.8(2) yes
C23 . C25 . C24 . 117.6(3) yes
C23 . C25 . C26 . 120.7(3) yes
C24 . C25 . C26 . 121.6(3) yes
C25 . C26 . C27 . 119.1(3) yes
C25 . C26 . H261 . 119.2 no
C27 . C26 . H261 . 121.8 no
C26 . C27 . C28 . 120.9(3) yes
C26 . C27 . H271 . 121.4 no
C28 . C27 . H271 . 117.7 no
C27 . C28 . C29 . 121.7(3) yes
C27 . C28 . H281 . 119.8 no
C29 . C28 . H281 . 118.5 no
C24 . C29 . C28 . 118.6(3) yes
C24 . C29 . O30 . 119.7(2) yes
C28 . C29 . O30 . 121.6(3) yes
C29 . O30 . H301 . 117(3) no
F102 . P101 . F103 . 91.5(2) yes
F102 . P101 . F104 . 90.79(14) yes
F103 . P101 . F104 . 87.23(18) yes
F102 . P101 . F105 . 90.73(18) yes
F103 . P101 . F105 . 175.89(19) yes
F104 . P101 . F105 . 89.26(15) yes
F102 . P101 . F106 . 89.77(16) yes
F103 . P101 . F106 . 93.7(2) yes
F104 . P101 . F106 . 178.88(15) yes
F105 . P101 . F106 . 89.76(18) yes
F102 . P101 . F107 . 177.60(18) yes
F103 . P101 . F107 . 90.84(19) yes
F104 . P101 . F107 . 88.63(12) yes
F105 . P101 . F107 . 86.93(14) yes
F106 . P101 . F107 . 90.76(14) yes
F112 . P111 . F113 . 89.94(11) yes
F112 . P111 . F114 . 90.07(10) yes
F113 . P111 . F114 . 90.39(11) yes
F112 . P111 . F115 . 91.02(11) yes
F113 . P111 . F115 . 178.97(11) yes
F114 . P111 . F115 . 89.25(11) yes
F112 . P111 . F116 . 89.89(10) yes
F113 . P111 . F116 . 90.67(11) yes
F114 . P111 . F116 . 178.94(11) yes
F115 . P111 . F116 . 89.69(11) yes
F112 . P111 . F117 . 179.31(11) yes
F113 . P111 . F117 . 89.42(10) yes
F114 . P111 . F117 . 89.65(10) yes
F115 . P111 . F117 . 89.61(11) yes
F116 . P111 . F117 . 90.40(10) yes
C203 . C202 . H2021 . 109.4 no
C203 . C202 . H2023 . 111.5 no
H2021 . C202 . H2023 . 107.6 no
C203 . C202 . H2022 . 109.9 no
H2021 . C202 . H2022 . 108.8 no
H2023 . C202 . H2022 . 109.6 no
C202 . C203 . O201 . 121.1(3) yes
C202 . C203 . C204 . 117.9(3) yes
O201 . C203 . C204 . 121.0(3) yes
C203 . C204 . H2041 . 109.6 no
C203 . C204 . H2043 . 109.2 no
H2041 . C204 . H2043 . 109.3 no
C203 . C204 . H2042 . 110.2 no
H2041 . C204 . H2042 . 109.5 no
H2043 . C204 . H2042 . 109.1 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
C12 . H122 . O30 . 134.86(7) 0.982 2.556 3.323(4) yes
C17 . H171 . C21 . 124.87(8) 0.934 2.561 3.188(4) yes
O1 . H11 . O201 2_766 174(4) 0.828 1.855 2.679(4) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 15/04/16 at 17: 2:35
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT O    (    1 ,X'S,U'S)  UNTIL C    (  204 ) 
CONT H    (   11 ,X'S)  UNTIL H    (  301 ) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 192,X'S) H   ( 191,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   ( 202,X'S) H   (2021,X'S) H   (2023,X'S) H   (2022,X'S) 
RIDE C   ( 204,X'S) H   (2041,X'S) H   (2043,X'S) H   (2042,X'S) 
END 
;

_iucr_refine_instructions_details_restraints 
;                                                                            
#
# Punched on 15/04/16 at 17: 2:35
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 1) TO H(11) 
REST 0.053, 0.002 = H(11,U[ISO]) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 30) TO H(301) 
REST 0.065, 0.002 = H(301,U[ISO]) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# 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_2PF6
_database_code_depnum_ccdc_archive 'CCDC 2050538'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;

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

_refine_special_details          
; 
Hydrogen atoms were visible in the Fourier difference map. O-H protons 
were refined with restraints on bond lengths and angles.  C-H protons were 
initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. 

Apart from restraints on O-H bond lengths and angles, it was not necessary
to use any crystallographic restraints.
;

_cell_length_a                   6.9715(3)
_cell_length_b                   8.8109(4)
_cell_length_c                   10.7517(4)
_cell_angle_alpha                105.053(4)
_cell_angle_beta                 99.409(4)
_cell_angle_gamma                94.776(4)
_cell_volume                     623.68(2)

_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'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

_chemical_formula_sum            'C10 H12 F6 N1 O2 P1'
_chemical_formula_moiety         'C10 H10 N O, F6 P, H2 O'
_chemical_compound_source        synthesized
_chemical_formula_weight         323.17

_cell_measurement_reflns_used    3808
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      29.2
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.13
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_max          0.23

_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             327.999
_exptl_absorpt_coefficient_mu    0.297

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_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    'Superflip (Palatinus & Chapuis, 2007)'
_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            7730
_reflns_number_total             2549
_diffrn_reflns_av_R_equivalents  0.021

_diffrn_reflns_theta_min         3.260
_diffrn_reflns_theta_max         26.366
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        26.366
_diffrn_measured_fraction_theta_full 0.998

_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              -11
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   2.42
_oxford_diffrn_Wilson_scale      0.06

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.46
_refine_diff_density_max         0.69

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         2540
_refine_ls_number_restraints     3
_refine_ls_number_parameters     190
_oxford_refine_ls_R_factor_ref   0.0509
_refine_ls_wR_factor_ref         0.1016
_refine_ls_goodness_of_fit_ref   0.9338
_refine_ls_shift/su_max          0.0004184
_refine_ls_shift/su_mean         0.0000322

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2540
_refine_ls_R_factor_all          0.0509
_refine_ls_wR_factor_all         0.1016

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2120
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_gt          0.0916

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    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: 
 414. 659. 386. 150. 30.0 
;

# 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 0.6998(3) 0.5331(2) 0.69879(17) 0.0231 1.0000 Uani . . . . . .
C2 C 0.6762(3) 0.6344(3) 0.8090(2) 0.0284 1.0000 Uani . . . . . .
C3 C 0.5151(4) 0.6153(3) 0.8669(2) 0.0308 1.0000 Uani . . . . . .
C4 C 0.3773(3) 0.4863(3) 0.8094(2) 0.0279 1.0000 Uani . . . . . .
C5 C 0.3953(3) 0.3777(3) 0.6915(2) 0.0241 1.0000 Uani . . . . . .
C6 C 0.2512(3) 0.2453(3) 0.6312(2) 0.0312 1.0000 Uani . . . . . .
C7 C 0.2688(4) 0.1420(3) 0.5161(2) 0.0345 1.0000 Uani . . . . . .
C8 C 0.4286(3) 0.1673(3) 0.4568(2) 0.0287 1.0000 Uani . . . . . .
C9 C 0.5739(3) 0.2937(3) 0.5123(2) 0.0230 1.0000 Uani . . . . . .
C10 C 0.5601(3) 0.4026(2) 0.6329(2) 0.0208 1.0000 Uani . . . . . .
C11 C 0.8853(3) 0.5647(3) 0.6531(2) 0.0344 1.0000 Uani . . . . . .
O12 O 0.7272(2) 0.3162(2) 0.45361(16) 0.0322 1.0000 Uani D . . . . .
P21 P 0.84800(8) 0.18527(6) 0.88368(5) 0.0229 1.0000 Uani . . . . . .
F21 F 0.6131(2) 0.1572(2) 0.86115(16) 0.0500 1.0000 Uani . . . . . .
F22 F 0.8634(2) 0.1987(2) 1.03604(15) 0.0515 1.0000 Uani . . . . . .
F23 F 0.8389(3) 0.36982(19) 0.91546(19) 0.0610 1.0000 Uani . . . . . .
F24 F 0.8302(2) 0.1744(2) 0.73181(14) 0.0450 1.0000 Uani . . . . . .
F25 F 0.8537(3) 0.00045(19) 0.8507(2) 0.0618 1.0000 Uani . . . . . .
F26 F 1.0812(2) 0.2135(2) 0.90578(15) 0.0437 1.0000 Uani . . . . . .
O101 O 0.2682(4) -0.0834(2) 0.7589(2) 0.0526 1.0000 Uani D . . . . .
H21 H 0.7769 0.7217 0.8505 0.0360 1.0000 Uiso R . . . . .
H31 H 0.5031 0.6902 0.9453 0.0372 1.0000 Uiso R . . . . .
H41 H 0.2675 0.4698 0.8492 0.0342 1.0000 Uiso R . . . . .
H61 H 0.1431 0.2293 0.6710 0.0385 1.0000 Uiso R . . . . .
H71 H 0.1728 0.0529 0.4741 0.0424 1.0000 Uiso R . . . . .
H81 H 0.4385 0.0937 0.3759 0.0354 1.0000 Uiso R . . . . .
H113 H 0.9511 0.4709 0.6465 0.0539 1.0000 Uiso R . . . . .
H112 H 0.8538 0.5848 0.5675 0.0539 1.0000 Uiso R . . . . .
H111 H 0.9635 0.6545 0.7172 0.0536 1.0000 Uiso R . . . . .
H121 H 0.719(5) 0.244(3) 0.387(2) 0.0497 1.0000 Uiso D . . . . .
H1012 H 0.206(5) -0.085(5) 0.815(3) 0.0781 1.0000 Uiso D . . . . .
H1011 H 0.354(5) -0.011(4) 0.791(4) 0.0782 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.34(7)

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 . 1.329(3) yes
N1 . C10 . 1.392(3) yes
N1 . C11 . 1.487(3) yes
C2 . C3 . 1.389(3) yes
C2 . H21 . 0.955 no
C3 . C4 . 1.363(3) yes
C3 . H31 . 0.948 no
C4 . C5 . 1.407(3) yes
C4 . H41 . 0.954 no
C5 . C6 . 1.411(3) yes
C5 . C10 . 1.425(3) yes
C6 . C7 . 1.363(3) yes
C6 . H61 . 0.943 no
C7 . C8 . 1.401(3) yes
C7 . H71 . 0.947 no
C8 . C9 . 1.375(3) yes
C8 . H81 . 0.957 no
C9 . C10 . 1.422(3) yes
C9 . O12 . 1.353(3) yes
C11 . H113 . 0.970 no
C11 . H112 . 0.976 no
C11 . H111 . 0.960 no
O12 . H121 . 0.816(17) no
P21 . F21 . 1.6044(15) yes
P21 . F22 . 1.5965(16) yes
P21 . F23 . 1.5813(17) yes
P21 . F24 . 1.5941(15) yes
P21 . F25 . 1.5794(17) yes
P21 . F26 . 1.5927(15) yes
O101 . H1012 . 0.799(18) no
O101 . H1011 . 0.799(18) 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 . C10 . 121.34(19) yes
C2 . N1 . C11 . 116.24(19) yes
C10 . N1 . C11 . 122.40(18) yes
N1 . C2 . C3 . 122.6(2) yes
N1 . C2 . H21 . 118.0 no
C3 . C2 . H21 . 119.4 no
C2 . C3 . C4 . 118.6(2) yes
C2 . C3 . H31 . 120.2 no
C4 . C3 . H31 . 121.1 no
C3 . C4 . C5 . 120.4(2) yes
C3 . C4 . H41 . 119.7 no
C5 . C4 . H41 . 119.9 no
C4 . C5 . C6 . 120.4(2) yes
C4 . C5 . C10 . 119.6(2) yes
C6 . C5 . C10 . 120.0(2) yes
C5 . C6 . C7 . 119.9(2) yes
C5 . C6 . H61 . 119.5 no
C7 . C6 . H61 . 120.6 no
C6 . C7 . C8 . 120.3(2) yes
C6 . C7 . H71 . 120.9 no
C8 . C7 . H71 . 118.8 no
C7 . C8 . C9 . 122.0(2) yes
C7 . C8 . H81 . 119.2 no
C9 . C8 . H81 . 118.8 no
C8 . C9 . C10 . 118.89(19) yes
C8 . C9 . O12 . 121.17(19) yes
C10 . C9 . O12 . 119.94(19) yes
C5 . C10 . C9 . 118.83(19) yes
C5 . C10 . N1 . 117.36(18) yes
C9 . C10 . N1 . 123.81(18) yes
N1 . C11 . H113 . 107.3 no
N1 . C11 . H112 . 108.9 no
H113 . C11 . H112 . 110.5 no
N1 . C11 . H111 . 107.9 no
H113 . C11 . H111 . 110.6 no
H112 . C11 . H111 . 111.5 no
C9 . O12 . H121 . 110(2) no
F21 . P21 . F22 . 90.62(9) yes
F21 . P21 . F23 . 88.80(11) yes
F22 . P21 . F23 . 89.09(11) yes
F21 . P21 . F24 . 88.80(9) yes
F22 . P21 . F24 . 178.96(10) yes
F23 . P21 . F24 . 90.03(10) yes
F21 . P21 . F25 . 90.37(10) yes
F22 . P21 . F25 . 91.27(11) yes
F23 . P21 . F25 . 179.10(10) yes
F24 . P21 . F25 . 89.59(11) yes
F21 . P21 . F26 . 179.82(10) yes
F22 . P21 . F26 . 89.50(8) yes
F23 . P21 . F26 . 91.07(10) yes
F24 . P21 . F26 . 91.07(8) yes
F25 . P21 . F26 . 89.75(10) yes
H1012 . O101 . H1011 . 105(4) no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O12 . H121 . O101 2_656 173(3) 0.816 1.839 2.651(3) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 19/09/17 at  9: 4:18
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL O    (  101 ) 
CONT H    (  121 ,X'S)  UNTIL H    ( 1011 ) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 112,X'S) H   ( 111,X'S) 
END   
;

_iucr_refine_instructions_details_restraints 
;                                                                          
#
# Punched on 19/09/17 at  9: 4:18
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 12) TO H(121) 
REST 0.049, 0.002 = H(121,U[ISO]) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 101) TO H(1012) 
CONT O ( 101) TO H(1011) 
REST 0.077, 0.002 = H(1012,U[ISO]) 
REST 0.077, 0.002 = H(1011,U[ISO]) 
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
1 -2 2 x .
####################################################################### 
# 
# 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_2SO4
_database_code_depnum_ccdc_archive 'CCDC 2050540'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;

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

_refine_special_details          
; 
The asymmetric unit contains one hydroxyquinolinium cation and a sulfate anion
located on a special position (such that overall there are two cations per 
anion). 

Hydrogen atoms were  visible in the Fourier difference 
map and were initially refined with restraints on bond lengths and angles, 
after which the positions were used as the basis for a riding model. The O-H 
hydrogen atom was refined with restraints on bond lengths and angles. 

Otherwise it was not necessary to use any crystallographic restraints.
;

_cell_length_a                   7.5285(3)
_cell_length_b                   17.4636(5)
_cell_length_c                   6.8720(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.350(3)
_cell_angle_gamma                90
_cell_volume                     891.49(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,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 0.0181 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'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

_chemical_formula_sum            'C20 H20 N2 O6 S1'
_chemical_formula_moiety         '2(C10 H10 N O), O4 S'
_chemical_compound_source        synthesized
_chemical_formula_weight         416.45

_cell_measurement_reflns_used    3344
_cell_measurement_theta_min      5.06
_cell_measurement_theta_max      73.4
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.01
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_max          0.28

_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    2.008

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.66
_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    'Superflip (Palatinus & Chapuis, 2007)'
_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            9169
_reflns_number_total             1787
_diffrn_reflns_av_R_equivalents  0.051

_diffrn_reflns_theta_min         5.065
_diffrn_reflns_theta_max         73.896
_diffrn_measured_fraction_theta_max 0.985

_diffrn_reflns_theta_full        67.246
_diffrn_measured_fraction_theta_full 0.995

_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       5
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              21
_reflns_limit_l_min              0
_reflns_limit_l_max              8

_oxford_diffrn_Wilson_B_factor   1.89
_oxford_diffrn_Wilson_scale      0.05

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.29
_refine_diff_density_max         0.28

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         1785
_refine_ls_number_restraints     1
_refine_ls_number_parameters     157
_oxford_refine_ls_R_factor_ref   0.0552
_refine_ls_wR_factor_ref         0.1190
_refine_ls_goodness_of_fit_ref   0.9467
_refine_ls_shift/su_max          0.0001245
_refine_ls_shift/su_mean         0.0000197

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1785
_refine_ls_R_factor_all          0.0552
_refine_ls_wR_factor_all         0.1190

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1508
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_gt          0.1114

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    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: 
 0.106E+04 0.176E+04 0.111E+04 497. 127. 
;

# 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
C1 C 0.5446(3) 0.14703(12) 0.0116(4) 0.0350 1.0000 Uani . . . . . .
N2 N 0.7400(2) 0.14519(9) 0.0876(2) 0.0246 1.0000 Uani . . . . . .
C3 C 0.8127(3) 0.07606(12) 0.1231(3) 0.0308 1.0000 Uani . . . . . .
C4 C 0.9945(3) 0.06546(12) 0.1950(3) 0.0325 1.0000 Uani . . . . . .
C5 C 1.1025(3) 0.12801(12) 0.2315(3) 0.0295 1.0000 Uani . . . . . .
C6 C 1.0318(3) 0.20254(11) 0.1952(3) 0.0252 1.0000 Uani . . . . . .
C7 C 0.8447(3) 0.21145(10) 0.1219(3) 0.0225 1.0000 Uani . . . . . .
C8 C 1.1446(3) 0.26688(12) 0.2329(3) 0.0294 1.0000 Uani . . . . . .
C9 C 1.0740(3) 0.33902(12) 0.1992(3) 0.0303 1.0000 Uani . . . . . .
C10 C 0.8899(3) 0.34870(11) 0.1293(3) 0.0272 1.0000 Uani . . . . . .
C11 C 0.7733(3) 0.28731(10) 0.0871(3) 0.0232 1.0000 Uani . . . . . .
O12 O 0.5990(2) 0.29799(8) 0.0147(2) 0.0313 1.0000 Uani D . . . . .
S1 S 0.4965(8) 0.4967(3) 0.0291(5) 0.0237 0.5000 Uani . . . . -1 .
O3 O 0.5344(4) 0.43382(15) -0.0993(4) 0.0281 0.5000 Uani . . . . -1 .
O1 O 0.5297(4) 0.57037(15) -0.0697(5) 0.0322 0.5000 Uani . . . . -1 .
O4 O 0.3088(4) 0.49314(17) 0.0591(5) 0.0353 0.5000 Uani . . . . -1 .
O2 O 0.6175(5) 0.49250(16) 0.2199(5) 0.0364 0.5000 Uani . . . . -1 .
H13 H 0.4880 0.1806 0.0970 0.0548 1.0000 Uiso R . . . . .
H12 H 0.5288 0.1668 -0.1238 0.0551 1.0000 Uiso R . . . . .
H11 H 0.5000 0.0950 0.0156 0.0553 1.0000 Uiso R . . . . .
H31 H 0.7343 0.0334 0.0952 0.0405 1.0000 Uiso R . . . . .
H41 H 1.0424 0.0158 0.2181 0.0419 1.0000 Uiso R . . . . .
H51 H 1.2303 0.1217 0.2801 0.0388 1.0000 Uiso R . . . . .
H81 H 1.2716 0.2584 0.2786 0.0374 1.0000 Uiso R . . . . .
H91 H 1.1518 0.3826 0.2219 0.0386 1.0000 Uiso R . . . . .
H101 H 0.8398 0.3990 0.1054 0.0353 1.0000 Uiso R . . . . .
H121 H 0.563(4) 0.3425(11) -0.001(4) 0.0509 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.29(15)

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
C1 . N2 . 1.479(3) yes
C1 . H13 . 0.975 no
C1 . H12 . 0.981 no
C1 . H11 . 0.971 no
N2 . C3 . 1.331(3) yes
N2 . C7 . 1.398(2) yes
C3 . C4 . 1.390(3) yes
C3 . H31 . 0.951 no
C4 . C5 . 1.361(3) yes
C4 . H41 . 0.943 no
C5 . C6 . 1.413(3) yes
C5 . H51 . 0.972 no
C6 . C7 . 1.425(3) yes
C6 . C8 . 1.407(3) yes
C7 . C11 . 1.435(2) yes
C8 . C9 . 1.372(3) yes
C8 . H81 . 0.968 no
C9 . C10 . 1.402(3) yes
C9 . H91 . 0.958 no
C10 . C11 . 1.386(3) yes
C10 . H101 . 0.960 no
C11 . O12 . 1.339(3) yes
O12 . H121 . 0.824(17) no
S1 . O3 . 1.466(6) yes
S1 . O1 . 1.494(5) yes
S1 . O4 . 1.462(6) yes
S1 . O2 . 1.471(5) yes

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
N2 . C1 . H13 . 107.9 no
N2 . C1 . H12 . 107.7 no
H13 . C1 . H12 . 111.2 no
N2 . C1 . H11 . 107.4 no
H13 . C1 . H11 . 111.0 no
H12 . C1 . H11 . 111.6 no
C1 . N2 . C3 . 116.08(17) yes
C1 . N2 . C7 . 122.85(16) yes
C3 . N2 . C7 . 121.07(18) yes
N2 . C3 . C4 . 122.5(2) yes
N2 . C3 . H31 . 116.8 no
C4 . C3 . H31 . 120.7 no
C3 . C4 . C5 . 118.89(19) yes
C3 . C4 . H41 . 120.6 no
C5 . C4 . H41 . 120.5 no
C4 . C5 . C6 . 120.7(2) yes
C4 . C5 . H51 . 120.0 no
C6 . C5 . H51 . 119.3 no
C5 . C6 . C7 . 119.05(18) yes
C5 . C6 . C8 . 120.2(2) yes
C7 . C6 . C8 . 120.70(18) yes
C6 . C7 . N2 . 117.82(16) yes
C6 . C7 . C11 . 118.79(17) yes
N2 . C7 . C11 . 123.39(18) yes
C6 . C8 . C9 . 119.7(2) yes
C6 . C8 . H81 . 118.2 no
C9 . C8 . H81 . 122.1 no
C8 . C9 . C10 . 120.20(19) yes
C8 . C9 . H91 . 119.5 no
C10 . C9 . H91 . 120.3 no
C9 . C10 . C11 . 122.39(18) yes
C9 . C10 . H101 . 120.5 no
C11 . C10 . H101 . 117.0 no
C7 . C11 . C10 . 118.17(18) yes
C7 . C11 . O12 . 120.56(17) yes
C10 . C11 . O12 . 121.27(17) yes
C11 . O12 . H121 . 117(2) no
O3 . S1 . O1 . 108.0(3) yes
O3 . S1 . O4 . 109.8(4) yes
O1 . S1 . O4 . 109.7(4) yes
O3 . S1 . O2 . 110.2(4) yes
O1 . S1 . O2 . 108.9(4) yes
O4 . S1 . O2 . 110.2(3) yes

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
C4 . H41 . O2 4_745 121.27(8) 0.943 2.559 3.153(3) yes
C5 . H51 . O3 3_655 163.70(8) 0.972 2.500 3.444(3) yes
C5 . H51 . O2 4_745 121.62(9) 0.972 2.530 3.151(3) yes
C10 . H101 . O3 . 127.06(7) 0.960 2.566 3.236(3) yes
C10 . H101 . O4 2_665 161.26(9) 0.960 2.380 3.303(3) yes
C10 . H101 . O2 . 142.36(8) 0.960 2.552 3.364(3) yes
O12 . H121 . O3 . 159(3) 0.824 1.732 2.520(3) yes
O12 . H121 . O1 2_665 155(3) 0.824 1.774 2.547(3) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 13/03/18 at 10:37:48
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT C    (    1 ,X'S,U'S)  UNTIL O    (    2 ) 
CONT H    (  121 ,X'S) 
RIDE C   (   1,X'S) H   (  13,X'S) H   (  12,X'S) H   (  11,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
END
;

_iucr_refine_instructions_details_restraints 
;
#
# Punched on 13/03/18 at 10:37:48
#
#LIST     16                                                                    
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 12) TO H(121) 
REST 0.049, 0.002 = H(121,U[ISO]) 
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
-1 0 2 x .
-3 0 8 x .
####################################################################### 
# 
# 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_2Cl
_database_code_depnum_ccdc_archive 'CCDC 2050539'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;

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

_refine_special_details          
; 
Hydrogen atoms were  visible in the Fourier difference 
map and were initially refined with restraints on bond lengths and angles, 
after which the positions were used as the basis for a riding model. The O-H 
hydrogen atom was refined with restraints on bond lengths and angles. 

Otherwise, it was not necessary to use any restraints during the refinement.
;

_cell_length_a                   5.17920(10)
_cell_length_b                   13.1666(3)
_cell_length_c                   6.8217(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.057(2)
_cell_angle_gamma                90
_cell_volume                     461.664(14)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21 '
_symmetry_space_group_name_Hall  'P 2yb'

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

_chemical_formula_sum            'C10 H10 Cl1 N1 O1'
_chemical_formula_moiety         'C10 H10 N1 O1, Cl'
_chemical_compound_source        synthesized
_chemical_formula_weight         195.65

_cell_measurement_reflns_used    2231
_cell_measurement_theta_min      7
_cell_measurement_theta_max      73
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.12
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_max          0.69

_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             203.999
_exptl_absorpt_coefficient_mu    3.302

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.68
_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    'Superflip (Palatinus & Chapuis, 2007)'
_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            3222
_reflns_number_total             1755
_diffrn_reflns_av_R_equivalents  0.017

_diffrn_reflns_theta_min         6.539
_diffrn_reflns_theta_max         73.681
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        73.681
_diffrn_measured_fraction_theta_full 0.998

_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_reflns_limit_h_min              -6
_reflns_limit_h_max              6
_reflns_limit_k_min              -16
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              8

_oxford_diffrn_Wilson_B_factor   2.28
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.26
_refine_diff_density_max         0.30

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         1748
_refine_ls_number_restraints     2
_refine_ls_number_parameters     122
_oxford_refine_ls_R_factor_ref   0.0411
_refine_ls_wR_factor_ref         0.1067
_refine_ls_goodness_of_fit_ref   0.9111
_refine_ls_shift/su_max          0.0006436
_refine_ls_shift/su_mean         0.0000564

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1748
_refine_ls_R_factor_all          0.0411
_refine_ls_wR_factor_all         0.1067

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1732
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_gt          0.1061

_refine_ls_abs_structure_Flack   0.031(18)
_refine_ls_abs_structure_details 'Flack (1983), 776 Friedel-pairs'

_chemical_absolute_configuration ad

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    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: 
 0.239E+04 0.405E+04 0.268E+04 0.124E+04 353. 
;

# 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
C1 C 0.3370(5) 0.50001(19) 0.6006(4) 0.0331 1.0000 Uani . . . . . .
N2 N 0.4467(3) 0.40042(17) 0.6721(3) 0.0278 1.0000 Uani . . . . . .
C3 C 0.3611(4) 0.3642(2) 0.8345(4) 0.0320 1.0000 Uani . . . . . .
C4 C 0.4544(5) 0.2734(2) 0.9234(4) 0.0357 1.0000 Uani . . . . . .
C5 C 0.6413(5) 0.2213(2) 0.8428(4) 0.0339 1.0000 Uani . . . . . .
C6 C 0.7396(4) 0.25776(19) 0.6709(4) 0.0300 1.0000 Uani . . . . . .
C7 C 0.6334(4) 0.34910(19) 0.5808(4) 0.0270 1.0000 Uani . . . . . .
C8 C 0.9336(5) 0.2033(2) 0.5878(4) 0.0336 1.0000 Uani . . . . . .
C9 C 1.0186(5) 0.2369(2) 0.4165(4) 0.0350 1.0000 Uani . . . . . .
C10 C 0.9135(4) 0.3256(2) 0.3251(3) 0.0337 1.0000 Uani . . . . . .
C11 C 0.7263(5) 0.3828(2) 0.4032(4) 0.0309 1.0000 Uani . . . . . .
O12 O 0.6261(4) 0.46822(17) 0.3141(3) 0.0434 1.0000 Uani D . . . . .
Cl1 Cl 0.87536(8) 0.53334(12) 0.96701(6) 0.0308 1.0000 Uani . . . . . .
H13 H 0.2615 0.4938 0.4634 0.0519 1.0000 Uiso R . . . . .
H12 H 0.4794 0.5482 0.6121 0.0524 1.0000 Uiso R . . . . .
H11 H 0.2054 0.5221 0.6826 0.0520 1.0000 Uiso R . . . . .
H31 H 0.2315 0.4011 0.8918 0.0394 1.0000 Uiso R . . . . .
H41 H 0.3864 0.2493 1.0362 0.0433 1.0000 Uiso R . . . . .
H51 H 0.7154 0.1610 0.9005 0.0416 1.0000 Uiso R . . . . .
H81 H 1.0070 0.1451 0.6504 0.0405 1.0000 Uiso R . . . . .
H91 H 1.1485 0.1994 0.3601 0.0442 1.0000 Uiso R . . . . .
H101 H 0.9713 0.3488 0.2059 0.0396 1.0000 Uiso R . . . . .
H121 H 0.699(7) 0.481(3) 0.216(4) 0.0647 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          12.9(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
C1 . N2 . 1.487(3) yes
C1 . H13 . 0.973 no
C1 . H12 . 0.969 no
C1 . H11 . 0.977 no
N2 . C3 . 1.331(3) yes
N2 . C7 . 1.389(3) yes
C3 . C4 . 1.399(3) yes
C3 . H31 . 0.951 no
C4 . C5 . 1.357(4) yes
C4 . H41 . 0.940 no
C5 . C6 . 1.418(3) yes
C5 . H51 . 0.946 no
C6 . C7 . 1.430(3) yes
C6 . C8 . 1.409(3) yes
C7 . C11 . 1.428(3) yes
C8 . C9 . 1.372(4) yes
C8 . H81 . 0.934 no
C9 . C10 . 1.402(4) yes
C9 . H91 . 0.954 no
C10 . C11 . 1.385(3) yes
C10 . H101 . 0.950 no
C11 . O12 . 1.352(3) yes
O12 . H121 . 0.826(18) 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
N2 . C1 . H13 . 109.5 no
N2 . C1 . H12 . 107.2 no
H13 . C1 . H12 . 110.2 no
N2 . C1 . H11 . 109.8 no
H13 . C1 . H11 . 110.5 no
H12 . C1 . H11 . 109.7 no
C1 . N2 . C3 . 115.88(19) yes
C1 . N2 . C7 . 122.7(2) yes
C3 . N2 . C7 . 121.3(2) yes
N2 . C3 . C4 . 122.3(2) yes
N2 . C3 . H31 . 118.9 no
C4 . C3 . H31 . 118.8 no
C3 . C4 . C5 . 118.8(2) yes
C3 . C4 . H41 . 120.0 no
C5 . C4 . H41 . 121.2 no
C4 . C5 . C6 . 120.7(2) yes
C4 . C5 . H51 . 121.9 no
C6 . C5 . H51 . 117.4 no
C5 . C6 . C7 . 118.9(2) yes
C5 . C6 . C8 . 120.4(2) yes
C7 . C6 . C8 . 120.7(2) yes
C6 . C7 . N2 . 117.9(2) yes
C6 . C7 . C11 . 118.3(2) yes
N2 . C7 . C11 . 123.7(2) yes
C6 . C8 . C9 . 119.8(2) yes
C6 . C8 . H81 . 120.2 no
C9 . C8 . H81 . 119.9 no
C8 . C9 . C10 . 120.0(2) yes
C8 . C9 . H91 . 119.5 no
C10 . C9 . H91 . 120.5 no
C9 . C10 . C11 . 122.2(2) yes
C9 . C10 . H101 . 120.2 no
C11 . C10 . H101 . 117.6 no
C7 . C11 . C10 . 118.9(2) yes
C7 . C11 . O12 . 119.3(2) yes
C10 . C11 . O12 . 121.9(2) yes
C11 . O12 . H121 . 110(3) no

_iucr_refine_instructions_details_constraints 
;
#
# Punched on 24/11/17 at 18:12:30
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT C    (    1 ,X'S,U'S)  UNTIL CL   (    1 ) 
CONT H    (  121 ,X'S) 
CONT ENANTIO 
RIDE C   (   1,X'S) H   (  13,X'S) H   (  12,X'S) H   (  11,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
END
;

_iucr_refine_instructions_details_restraints 
;                                                                             
#
# Punched on 24/11/17 at 18:12:30
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 12) TO H(121) 
REST 0.065, 0.002 = H(121,U[ISO]) 
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
1 -2 1 x .
1 2 1 x .
####################################################################### 
# 
# 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_3PF6_acetonitrile
_database_code_depnum_ccdc_archive 'CCDC 2050542'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
The asymmetric unit cell contains the two bis-quinolinium cations, four 
hexafluorophosphate anions and five acetonitrile molecules. One PF6 anion
exhibits positional disorder, which was modeled by having two positions for 
the four equatorial fluorine atoms. It was necessary to apply restraints to 
the bond lengths and angles, and thermal and vibrational ellipsoid parameters 
of this disordered molecule in order to achieve a sensible refinement.

C-H hydrogen atoms were generally visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. O-H hydrogen 
atoms were visible in the Fourier difference map and were refined
with restraints on bond lengths and angles. 

Otherwise, it was not necessary to use any crystallographic restraints
in the final refinement.
;

_cell_length_a                   14.8499(5)
_cell_length_b                   16.5325(6)
_cell_length_c                   18.0268(7)
_cell_angle_alpha                65.052(4)
_cell_angle_beta                 66.010(3)
_cell_angle_gamma                88.251(3)
_cell_volume                     3612.62(14)

_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 0.0181 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'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

_chemical_formula_sum            'C64 H62 F24 N10 O4 P4'
_chemical_formula_moiety         '2(C26 H22 N2 O2), 4(F6 P), 6(C2 H3 N)'
_chemical_compound_source        synthesized
_chemical_formula_weight         1615.12

_cell_measurement_temperature    150
_cell_measurement_reflns_used    30196
_cell_measurement_theta_min      2.9420
_cell_measurement_theta_max      72.4980

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.15
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.34

_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1648
_exptl_absorpt_coefficient_mu    2.005

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_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            70361
_reflns_number_total             14267
_diffrn_reflns_av_R_equivalents  0.030

_diffrn_reflns_theta_min         2.992
_diffrn_reflns_theta_max         72.821
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        71.364
_diffrn_measured_fraction_theta_full 0.998

_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -16
_reflns_limit_h_max              18
_reflns_limit_k_min              -18
_reflns_limit_k_max              20
_reflns_limit_l_min              0
_reflns_limit_l_max              22

_oxford_diffrn_Wilson_B_factor   3.36
_oxford_diffrn_Wilson_scale      0.34

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.67
_refine_diff_density_max         0.87

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         14207
_refine_ls_number_restraints     123
_refine_ls_number_parameters     1003
_oxford_refine_ls_R_factor_ref   0.0689
_refine_ls_wR_factor_ref         0.1874
_refine_ls_goodness_of_fit_ref   0.9718
_refine_ls_shift/su_max          0.0003669
_refine_ls_shift/su_mean         0.0000322

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        14207
_refine_ls_R_factor_all          0.0689
_refine_ls_wR_factor_all         0.1874

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                12871
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_gt          0.1831

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    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: 
 0.137E+04 0.232E+04 0.141E+04 571. 122. 
;

# 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
O1 O 0.28361(14) 0.58026(11) 0.45179(11) 0.0402 1.0000 Uani D . . . . .
C2 C 0.19966(17) 0.57724(14) 0.52129(14) 0.0316 1.0000 Uani . . . . . .
C3 C 0.1183(2) 0.51022(16) 0.56403(18) 0.0417 1.0000 Uani . . . . . .
C4 C 0.0316(2) 0.50333(18) 0.6385(2) 0.0497 1.0000 Uani . . . . . .
C5 C 0.0241(2) 0.56554(19) 0.67037(19) 0.0500 1.0000 Uani . . . . . .
C6 C 0.10394(17) 0.63750(17) 0.62777(16) 0.0381 1.0000 Uani . . . . . .
C7 C 0.19335(16) 0.64490(14) 0.55204(14) 0.0296 1.0000 Uani . . . . . .
C8 C 0.0967(2) 0.7031(2) 0.66034(18) 0.0483 1.0000 Uani . . . . . .
C9 C 0.1721(2) 0.7733(2) 0.61912(19) 0.0495 1.0000 Uani . . . . . .
C10 C 0.25788(19) 0.77861(17) 0.54544(17) 0.0413 1.0000 Uani . . . . . .
N11 N 0.26914(13) 0.71764(13) 0.51366(12) 0.0309 1.0000 Uani . . . . . .
C12 C 0.36774(16) 0.73013(16) 0.43818(14) 0.0325 1.0000 Uani . . . . . .
C13 C 0.36629(14) 0.76862(13) 0.34631(13) 0.0250 1.0000 Uani . . . . . .
C14 C 0.29829(15) 0.82404(14) 0.32760(15) 0.0309 1.0000 Uani . . . . . .
C15 C 0.30097(16) 0.86225(15) 0.24157(16) 0.0351 1.0000 Uani . . . . . .
C16 C 0.37194(18) 0.84605(16) 0.17357(16) 0.0367 1.0000 Uani . . . . . .
C17 C 0.44038(16) 0.79030(15) 0.19145(14) 0.0303 1.0000 Uani . . . . . .
C18 C 0.43861(14) 0.75171(13) 0.27681(13) 0.0242 1.0000 Uani . . . . . .
C19 C 0.51006(15) 0.68815(13) 0.29773(14) 0.0269 1.0000 Uani . . . . . .
N20 N 0.60770(12) 0.70932(11) 0.21702(11) 0.0255 1.0000 Uani . . . . . .
C21 C 0.62153(17) 0.65268(15) 0.17984(16) 0.0326 1.0000 Uani . . . . . .
C22 C 0.70834(18) 0.66360(16) 0.10409(16) 0.0367 1.0000 Uani . . . . . .
C23 C 0.78187(17) 0.73507(16) 0.06582(15) 0.0340 1.0000 Uani . . . . . .
C24 C 0.68093(15) 0.78315(13) 0.18172(13) 0.0244 1.0000 Uani . . . . . .
C25 C 0.77051(15) 0.79669(14) 0.10336(14) 0.0277 1.0000 Uani . . . . . .
C26 C 0.84745(16) 0.87029(15) 0.06406(15) 0.0321 1.0000 Uani . . . . . .
C27 C 0.83633(17) 0.92894(15) 0.10147(16) 0.0335 1.0000 Uani . . . . . .
C28 C 0.74944(16) 0.91571(14) 0.17886(15) 0.0310 1.0000 Uani . . . . . .
C29 C 0.67249(15) 0.84454(14) 0.22023(14) 0.0263 1.0000 Uani . . . . . .
O30 O 0.58994(11) 0.83091(11) 0.29642(11) 0.0334 1.0000 Uani D . . . . .
O51 O 0.07515(11) 0.31742(11) 0.81038(11) 0.0326 1.0000 Uani D . . . . .
C52 C 0.15741(15) 0.32986(14) 0.73402(14) 0.0271 1.0000 Uani . . . . . .
C53 C 0.23487(16) 0.40064(14) 0.69220(15) 0.0315 1.0000 Uani . . . . . .
C54 C 0.32077(17) 0.41336(16) 0.61440(16) 0.0355 1.0000 Uani . . . . . .
C55 C 0.33048(17) 0.35416(16) 0.57785(15) 0.0355 1.0000 Uani . . . . . .
C56 C 0.25350(16) 0.27998(15) 0.61882(14) 0.0307 1.0000 Uani . . . . . .
C57 C 0.16439(15) 0.26730(14) 0.69743(13) 0.0262 1.0000 Uani . . . . . .
C58 C 0.26497(19) 0.21563(17) 0.58437(16) 0.0382 1.0000 Uani . . . . . .
C59 C 0.1924(2) 0.14254(18) 0.62581(18) 0.0425 1.0000 Uani . . . . . .
C60 C 0.10548(19) 0.13327(16) 0.70070(17) 0.0365 1.0000 Uani . . . . . .
N61 N 0.09068(13) 0.19287(12) 0.73458(12) 0.0279 1.0000 Uani . . . . . .
C62 C -0.00917(15) 0.17592(13) 0.81222(14) 0.0278 1.0000 Uani . . . . . .
C63 C -0.07651(15) 0.24075(13) 0.78448(14) 0.0268 1.0000 Uani . . . . . .
C64 C -0.07402(17) 0.26956(15) 0.69927(15) 0.0318 1.0000 Uani . . . . . .
C65 C -0.13896(19) 0.32497(16) 0.67419(16) 0.0385 1.0000 Uani . . . . . .
C66 C -0.20707(18) 0.35216(16) 0.73424(17) 0.0395 1.0000 Uani . . . . . .
C67 C -0.21023(17) 0.32443(16) 0.81986(17) 0.0377 1.0000 Uani . . . . . .
C68 C -0.14555(15) 0.26879(14) 0.84568(14) 0.0294 1.0000 Uani . . . . . .
C69 C -0.14665(16) 0.24142(18) 0.93786(15) 0.0370 1.0000 Uani . . . . . .
N70 N -0.24379(14) 0.24181(13) 1.00785(12) 0.0317 1.0000 Uani . . . . . .
C71 C -0.2485(2) 0.31389(18) 1.02431(19) 0.0455 1.0000 Uani . . . . . .
C72 C -0.3301(3) 0.3204(2) 1.0932(2) 0.0605 1.0000 Uani . . . . . .
C73 C -0.4082(2) 0.2514(3) 1.1468(2) 0.0601 1.0000 Uani . . . . . .
C74 C -0.32335(17) 0.17061(15) 1.05766(15) 0.0332 1.0000 Uani . . . . . .
C75 C -0.40795(19) 0.1757(2) 1.13048(17) 0.0476 1.0000 Uani . . . . . .
C76 C -0.4895(2) 0.1039(3) 1.1856(2) 0.0768 1.0000 Uani . . . . . .
C77 C -0.4893(3) 0.0309(3) 1.1684(3) 0.0895 1.0000 Uani . . . . . .
C78 C -0.4080(3) 0.0270(2) 1.0968(3) 0.0702 1.0000 Uani . . . . . .
C79 C -0.3259(2) 0.09394(16) 1.04181(18) 0.0446 1.0000 Uani . . . . . .
O80 O -0.24670(19) 0.08839(12) 0.97262(14) 0.0550 1.0000 Uani D . . . . .
P101 P 0.26978(5) 1.04507(5) 0.43481(5) 0.0452 1.0000 Uani . . . . . .
F102 F 0.34054(16) 1.11932(15) 0.4283(2) 0.0908 1.0000 Uani . . . . . .
F103 F 0.17828(14) 1.09513(14) 0.46586(14) 0.0647 1.0000 Uani . . . . . .
F104 F 0.24911(16) 0.98615(13) 0.53792(12) 0.0659 1.0000 Uani . . . . . .
F105 F 0.36005(14) 0.99324(15) 0.40561(13) 0.0730 1.0000 Uani . . . . . .
F106 F 0.2854(2) 1.1017(2) 0.33443(14) 0.1088 1.0000 Uani . . . . . .
F107 F 0.19444(18) 0.96805(18) 0.4473(2) 0.0893 1.0000 Uani . . . . . .
P111 P 0.41658(5) 0.62347(4) 0.67536(4) 0.0359 1.0000 Uani . . . . . .
F112 F 0.3365(2) 0.59079(15) 0.6529(2) 0.0943 1.0000 Uani . . . . . .
F113 F 0.47263(17) 0.69861(13) 0.57343(12) 0.0721 1.0000 Uani . . . . . .
F114 F 0.48294(17) 0.55222(14) 0.65306(14) 0.0812 1.0000 Uani . . . . . .
F115 F 0.36055(18) 0.54844(13) 0.77765(13) 0.0778 1.0000 Uani . . . . . .
F116 F 0.34985(16) 0.69278(12) 0.69949(15) 0.0755 1.0000 Uani . . . . . .
F117 F 0.4953(2) 0.65737(18) 0.6980(2) 0.1016 1.0000 Uani . . . . . .
P121 P -0.20744(5) 0.59168(5) 0.89243(5) 0.0486 1.0000 Uani . . . . . .
F122 F -0.16795(19) 0.66645(17) 0.91084(17) 0.0887 1.0000 Uani . . . . . .
F123 F -0.2605(2) 0.52866(17) 0.99930(16) 0.0955 1.0000 Uani . . . . . .
F124 F -0.11191(17) 0.5446(2) 0.88773(17) 0.0917 1.0000 Uani . . . . . .
F125 F -0.15145(16) 0.65653(16) 0.78700(14) 0.0780 1.0000 Uani . . . . . .
F126 F -0.30417(14) 0.63583(16) 0.8969(2) 0.0993 1.0000 Uani . . . . . .
F127 F -0.2485(2) 0.51761(16) 0.8748(2) 0.0873 1.0000 Uani . . . . . .
P131 P 0.09143(5) 0.85041(4) 0.83832(4) 0.0393 1.0000 Uani D U . . . .
F134 F 0.0601(4) 0.7961(4) 0.7963(4) 0.0777 0.6000 Uani D U . . 1 .
F137 F 0.03740(15) 0.76813(14) 0.93695(11) 0.0677 1.0000 Uani D U . . . .
F133 F -0.0097(5) 0.8883(6) 0.8548(5) 0.1121 0.6000 Uani D U . . 1 .
F132 F 0.1448(2) 0.93186(14) 0.73961(13) 0.0883 1.0000 Uani D U . . . .
F135 F 0.1886(4) 0.8069(5) 0.8250(5) 0.0963 0.6000 Uani D U . . 1 .
F136 F 0.1196(6) 0.8990(5) 0.8856(5) 0.1142 0.6000 Uani D U . . 1 .
N201 N 0.0781(4) 0.9479(5) 0.3120(6) 0.1783 1.0000 Uani . . . . . .
C202 C 0.0598(3) 1.0051(4) 0.3312(4) 0.1032 1.0000 Uani . . . . . .
C203 C 0.0360(3) 1.0769(4) 0.3545(4) 0.0920 1.0000 Uani . . . . . .
N211 N 0.59050(18) 0.95214(17) 0.36092(18) 0.0513 1.0000 Uani . . . . . .
C212 C 0.59182(19) 1.01603(18) 0.36934(18) 0.0409 1.0000 Uani . . . . . .
C213 C 0.5925(2) 1.09853(19) 0.3798(2) 0.0532 1.0000 Uani . . . . . .
N221 N 0.2670(3) 0.44571(19) 0.3990(2) 0.0750 1.0000 Uani . . . . . .
C222 C 0.2618(3) 0.3900(2) 0.3784(2) 0.0636 1.0000 Uani . . . . . .
C223 C 0.2618(4) 0.3202(3) 0.3496(3) 0.0876 1.0000 Uani . . . . . .
N224 N 0.08219(18) 0.44480(17) 0.86712(17) 0.0513 1.0000 Uani . . . . . .
C225 C 0.09425(18) 0.50645(17) 0.87644(17) 0.0397 1.0000 Uani . . . . . .
C226 C 0.1090(2) 0.5853(2) 0.8887(2) 0.0561 1.0000 Uani . . . . . .
N241 N 0.4749(3) 0.6767(4) 0.0540(4) 0.1138 1.0000 Uani . . . . . .
C242 C 0.4764(3) 0.6012(4) 0.0779(3) 0.0782 1.0000 Uani . . . . . .
C243 C 0.4791(4) 0.5068(4) 0.1106(4) 0.1146 1.0000 Uani . . . . . .
N251 N 0.2889(5) 1.0535(2) 0.0596(3) 0.1208 1.0000 Uani . . . . . .
C252 C 0.2909(4) 1.0990(2) 0.0905(3) 0.0831 1.0000 Uani . . . . . .
C253 C 0.2902(4) 1.1583(3) 0.1315(3) 0.0923 1.0000 Uani . . . . . .
H31 H 0.1231 0.4689 0.5418 0.0528 1.0000 Uiso R . . . . .
H41 H -0.0196 0.4532 0.6691 0.0624 1.0000 Uiso R . . . . .
H51 H -0.0334 0.5642 0.7186 0.0625 1.0000 Uiso R . . . . .
H81 H 0.0405 0.6980 0.7129 0.0581 1.0000 Uiso R . . . . .
H91 H 0.1672 0.8174 0.6402 0.0603 1.0000 Uiso R . . . . .
H101 H 0.3119 0.8275 0.5159 0.0510 1.0000 Uiso R . . . . .
H122 H 0.4141 0.7720 0.4364 0.0395 1.0000 Uiso R . . . . .
H121 H 0.3894 0.6714 0.4529 0.0405 1.0000 Uiso R . . . . .
H141 H 0.2523 0.8357 0.3727 0.0380 1.0000 Uiso R . . . . .
H151 H 0.2557 0.8989 0.2282 0.0425 1.0000 Uiso R . . . . .
H161 H 0.3746 0.8722 0.1156 0.0453 1.0000 Uiso R . . . . .
H171 H 0.4890 0.7775 0.1441 0.0386 1.0000 Uiso R . . . . .
H191 H 0.5223 0.6909 0.3465 0.0336 1.0000 Uiso R . . . . .
H192 H 0.4770 0.6265 0.3194 0.0332 1.0000 Uiso R . . . . .
H211 H 0.5692 0.6024 0.2082 0.0406 1.0000 Uiso R . . . . .
H221 H 0.7146 0.6211 0.0812 0.0467 1.0000 Uiso R . . . . .
H231 H 0.8407 0.7430 0.0157 0.0422 1.0000 Uiso R . . . . .
H261 H 0.9047 0.8772 0.0149 0.0412 1.0000 Uiso R . . . . .
H271 H 0.8862 0.9793 0.0750 0.0422 1.0000 Uiso R . . . . .
H281 H 0.7390 0.9521 0.2061 0.0387 1.0000 Uiso R . . . . .
H531 H 0.2308 0.4406 0.7178 0.0388 1.0000 Uiso R . . . . .
H541 H 0.3721 0.4644 0.5867 0.0436 1.0000 Uiso R . . . . .
H551 H 0.3894 0.3600 0.5253 0.0446 1.0000 Uiso R . . . . .
H581 H 0.3239 0.2229 0.5334 0.0465 1.0000 Uiso R . . . . .
H591 H 0.2013 0.0995 0.6046 0.0520 1.0000 Uiso R . . . . .
H601 H 0.0560 0.0826 0.7290 0.0449 1.0000 Uiso R . . . . .
H621 H -0.0444 0.1169 0.8345 0.0340 1.0000 Uiso R . . . . .
H622 H 0.0000 0.1810 0.8603 0.0339 1.0000 Uiso R . . . . .
H641 H -0.0275 0.2490 0.6613 0.0399 1.0000 Uiso R . . . . .
H651 H -0.1384 0.3414 0.6177 0.0471 1.0000 Uiso R . . . . .
H661 H -0.2521 0.3884 0.7196 0.0497 1.0000 Uiso R . . . . .
H671 H -0.2579 0.3449 0.8625 0.0457 1.0000 Uiso R . . . . .
H691 H -0.1320 0.1786 0.9601 0.0466 1.0000 Uiso R . . . . .
H692 H -0.0964 0.2830 0.9313 0.0470 1.0000 Uiso R . . . . .
H711 H -0.1936 0.3577 0.9904 0.0550 1.0000 Uiso R . . . . .
H721 H -0.3313 0.3720 1.1030 0.0723 1.0000 Uiso R . . . . .
H731 H -0.4643 0.2529 1.1954 0.0712 1.0000 Uiso R . . . . .
H761 H -0.5416 0.1072 1.2326 0.0940 1.0000 Uiso R . . . . .
H771 H -0.5427 -0.0165 1.2033 0.1051 1.0000 Uiso R . . . . .
H781 H -0.4107 -0.0250 1.0859 0.0823 1.0000 Uiso R . . . . .
H2031 H 0.0482 1.0650 0.4066 0.1356 1.0000 Uiso R . . . . .
H2033 H 0.0761 1.1335 0.3017 0.1363 1.0000 Uiso R . . . . .
H2032 H -0.0342 1.0790 0.3697 0.1356 1.0000 Uiso R . . . . .
H2133 H 0.6072 1.0865 0.4314 0.0821 1.0000 Uiso R . . . . .
H2132 H 0.6419 1.1463 0.3258 0.0816 1.0000 Uiso R . . . . .
H2131 H 0.5293 1.1180 0.3905 0.0828 1.0000 Uiso R . . . . .
H2262 H 0.1260 0.5744 0.9369 0.0857 1.0000 Uiso R . . . . .
H2261 H 0.0500 0.6124 0.8995 0.0868 1.0000 Uiso R . . . . .
H2263 H 0.1590 0.6313 0.8337 0.0863 1.0000 Uiso R . . . . .
H2431 H 0.4308 0.4752 0.1029 0.1605 1.0000 Uiso R . . . . .
H2433 H 0.5465 0.4998 0.0755 0.1607 1.0000 Uiso R . . . . .
H2432 H 0.4661 0.4824 0.1737 0.1602 1.0000 Uiso R . . . . .
H2531 H 0.3520 1.2025 0.0955 0.1401 1.0000 Uiso R . . . . .
H2533 H 0.2798 1.1243 0.1942 0.1394 1.0000 Uiso R . . . . .
H2532 H 0.2353 1.1917 0.1337 0.1400 1.0000 Uiso R . . . . .
H301 H 0.598(2) 0.8740(17) 0.307(2) 0.0510 1.0000 Uiso D . . . . .
H11 H 0.278(3) 0.5390(19) 0.441(2) 0.0623 1.0000 Uiso D . . . . .
H511 H 0.075(2) 0.3556(18) 0.828(2) 0.0512 1.0000 Uiso D . . . . .
H801 H -0.265(3) 0.044(2) 0.971(3) 0.0831 1.0000 Uiso D . . . . .
H2231 H 0.1956 0.2883 0.3779 0.1041 1.0000 Uiso R . . . . .
H2232 H 0.2853 0.3477 0.2855 0.1041 1.0000 Uiso R . . . . .
H2233 H 0.3042 0.2792 0.3663 0.1041 1.0000 Uiso R . . . . .
F146 F 0.1669(8) 0.8867(6) 0.8628(8) 0.1120 0.4000 Uani D U . . 2 .
F145 F 0.1676(7) 0.7922(5) 0.8101(7) 0.1179 0.4000 Uani D U . . 2 .
F144 F 0.0191(8) 0.8168(8) 0.8113(7) 0.1649 0.4000 Uani D U . . 2 .
F143 F 0.0225(7) 0.9182(7) 0.8609(7) 0.1293 0.4000 Uani D U . . 2 .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.956(13)

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 . C2 . 1.344(3) yes
O1 . H11 . 0.794(18) no
C2 . C3 . 1.373(3) yes
C2 . C7 . 1.429(3) yes
C3 . C4 . 1.396(4) yes
C3 . H31 . 0.915 no
C4 . C5 . 1.356(4) yes
C4 . H41 . 0.938 no
C5 . C6 . 1.409(3) yes
C5 . H51 . 0.931 no
C6 . C7 . 1.427(3) yes
C6 . C8 . 1.418(3) yes
C7 . N11 . 1.393(3) yes
C8 . C9 . 1.352(4) yes
C8 . H81 . 0.946 no
C9 . C10 . 1.388(3) yes
C9 . H91 . 0.944 no
C10 . N11 . 1.331(3) yes
C10 . H101 . 0.954 no
N11 . C12 . 1.483(3) yes
C12 . C13 . 1.512(3) yes
C12 . H122 . 0.973 no
C12 . H121 . 0.975 no
C13 . C14 . 1.390(3) yes
C13 . C18 . 1.409(3) yes
C14 . C15 . 1.389(3) yes
C14 . H141 . 0.915 no
C15 . C16 . 1.376(3) yes
C15 . H151 . 0.928 no
C16 . C17 . 1.395(3) yes
C16 . H161 . 0.930 no
C17 . C18 . 1.384(3) yes
C17 . H171 . 0.967 no
C18 . C19 . 1.515(3) yes
C19 . N20 . 1.493(2) yes
C19 . H191 . 0.987 no
C19 . H192 . 0.985 no
N20 . C21 . 1.332(3) yes
N20 . C24 . 1.393(3) yes
C21 . C22 . 1.391(3) yes
C21 . H211 . 0.957 no
C22 . C23 . 1.358(3) yes
C22 . H221 . 0.939 no
C23 . C25 . 1.415(3) yes
C23 . H231 . 0.929 no
C24 . C25 . 1.428(3) yes
C24 . C29 . 1.429(3) yes
C25 . C26 . 1.410(3) yes
C26 . C27 . 1.369(3) yes
C26 . H261 . 0.910 no
C27 . C28 . 1.398(3) yes
C27 . H271 . 0.941 no
C28 . C29 . 1.377(3) yes
C28 . H281 . 0.900 no
C29 . O30 . 1.351(2) yes
O30 . H301 . 0.831(17) no
O51 . C52 . 1.356(2) yes
O51 . H511 . 0.816(17) no
C52 . C53 . 1.376(3) yes
C52 . C57 . 1.424(3) yes
C53 . C54 . 1.397(3) yes
C53 . H531 . 0.940 no
C54 . C55 . 1.368(3) yes
C54 . H541 . 0.958 no
C55 . C56 . 1.411(3) yes
C55 . H551 . 0.963 no
C56 . C57 . 1.430(3) yes
C56 . C58 . 1.417(3) yes
C57 . N61 . 1.397(3) yes
C58 . C59 . 1.357(4) yes
C58 . H581 . 0.940 no
C59 . C60 . 1.390(3) yes
C59 . H591 . 0.923 no
C60 . N61 . 1.333(3) yes
C60 . H601 . 0.935 no
N61 . C62 . 1.498(3) yes
C62 . C63 . 1.513(3) yes
C62 . H621 . 0.958 no
C62 . H622 . 0.966 no
C63 . C64 . 1.388(3) yes
C63 . C68 . 1.402(3) yes
C64 . C65 . 1.387(3) yes
C64 . H641 . 0.927 no
C65 . C66 . 1.374(4) yes
C65 . H651 . 0.933 no
C66 . C67 . 1.393(3) yes
C66 . H661 . 0.928 no
C67 . C68 . 1.390(3) yes
C67 . H671 . 0.985 no
C68 . C69 . 1.520(3) yes
C69 . N70 . 1.483(3) yes
C69 . H691 . 0.997 no
C69 . H692 . 0.967 no
N70 . C71 . 1.338(3) yes
N70 . C74 . 1.385(3) yes
C71 . C72 . 1.380(4) yes
C71 . H711 . 0.905 no
C72 . C73 . 1.348(5) yes
C72 . H721 . 0.941 no
C73 . C75 . 1.400(5) yes
C73 . H731 . 0.942 no
C74 . C75 . 1.433(3) yes
C74 . C79 . 1.417(3) yes
C75 . C76 . 1.407(4) yes
C76 . C77 . 1.365(7) yes
C76 . H761 . 0.907 no
C77 . C78 . 1.388(6) yes
C77 . H771 . 0.925 no
C78 . C79 . 1.367(4) yes
C78 . H781 . 0.964 no
C79 . O80 . 1.358(4) yes
O80 . H801 . 0.803(18) no
P101 . F102 . 1.575(2) yes
P101 . F103 . 1.5964(17) yes
P101 . F104 . 1.5890(19) yes
P101 . F105 . 1.5953(17) yes
P101 . F106 . 1.564(2) yes
P101 . F107 . 1.601(2) yes
P111 . F112 . 1.577(2) yes
P111 . F113 . 1.5831(18) yes
P111 . F114 . 1.5897(18) yes
P111 . F115 . 1.5865(18) yes
P111 . F116 . 1.5762(18) yes
P111 . F117 . 1.571(2) yes
P121 . F122 . 1.591(2) yes
P121 . F123 . 1.594(2) yes
P121 . F124 . 1.587(2) yes
P121 . F125 . 1.582(2) yes
P121 . F126 . 1.579(2) yes
P121 . F127 . 1.582(2) yes
P131 . F134 . 1.577(4) yes
P131 . F137 . 1.5879(17) yes
P131 . F133 . 1.573(5) yes
P131 . F132 . 1.5828(19) yes
P131 . F135 . 1.568(4) yes
P131 . F136 . 1.561(4) yes
N201 . C202 . 1.129(6) yes
C202 . C203 . 1.408(6) yes
C203 . H2031 . 0.968 no
C203 . H2033 . 0.979 no
C203 . H2032 . 0.968 no
N211 . C212 . 1.131(3) yes
C212 . C213 . 1.454(3) yes
C213 . H2133 . 0.979 no
C213 . H2132 . 0.958 no
C213 . H2131 . 0.952 no
N221 . C222 . 1.143(4) yes
C222 . C223 . 1.451(4) yes
C223 . H2231 . 0.950 no
C223 . H2232 . 0.950 no
C223 . H2233 . 0.950 no
N224 . C225 . 1.131(3) yes
C225 . C226 . 1.448(3) yes
C226 . H2262 . 0.947 no
C226 . H2261 . 0.958 no
C226 . H2263 . 0.955 no
N241 . C242 . 1.137(7) yes
C242 . C243 . 1.424(8) yes
C243 . H2431 . 0.984 no
C243 . H2433 . 0.977 no
C243 . H2432 . 0.967 no
N251 . C252 . 1.116(4) yes
C252 . C253 . 1.452(5) yes
C253 . H2531 . 0.977 no
C253 . H2533 . 0.972 no
C253 . H2532 . 0.967 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 . O1 . H11 . 111(3) no
O1 . C2 . C3 . 121.5(2) yes
O1 . C2 . C7 . 120.12(19) yes
C3 . C2 . C7 . 118.4(2) yes
C2 . C3 . C4 . 122.8(2) yes
C2 . C3 . H31 . 116.9 no
C4 . C3 . H31 . 120.3 no
C3 . C4 . C5 . 120.1(2) yes
C3 . C4 . H41 . 119.7 no
C5 . C4 . H41 . 120.0 no
C4 . C5 . C6 . 119.8(2) yes
C4 . C5 . H51 . 122.5 no
C6 . C5 . H51 . 117.7 no
C5 . C6 . C7 . 120.6(2) yes
C5 . C6 . C8 . 120.2(2) yes
C7 . C6 . C8 . 119.2(2) yes
C2 . C7 . C6 . 118.20(19) yes
C2 . C7 . N11 . 124.46(19) yes
C6 . C7 . N11 . 117.34(19) yes
C6 . C8 . C9 . 120.8(2) yes
C6 . C8 . H81 . 121.5 no
C9 . C8 . H81 . 117.7 no
C8 . C9 . C10 . 118.5(2) yes
C8 . C9 . H91 . 121.0 no
C10 . C9 . H91 . 120.4 no
C9 . C10 . N11 . 122.9(2) yes
C9 . C10 . H101 . 119.5 no
N11 . C10 . H101 . 117.7 no
C7 . N11 . C10 . 121.26(19) yes
C7 . N11 . C12 . 122.63(18) yes
C10 . N11 . C12 . 116.07(19) yes
N11 . C12 . C13 . 113.61(17) yes
N11 . C12 . H122 . 107.3 no
C13 . C12 . H122 . 108.4 no
N11 . C12 . H121 . 107.2 no
C13 . C12 . H121 . 110.9 no
H122 . C12 . H121 . 109.2 no
C12 . C13 . C14 . 121.41(19) yes
C12 . C13 . C18 . 119.27(18) yes
C14 . C13 . C18 . 119.25(19) yes
C13 . C14 . C15 . 120.7(2) yes
C13 . C14 . H141 . 118.9 no
C15 . C14 . H141 . 120.5 no
C14 . C15 . C16 . 120.1(2) yes
C14 . C15 . H151 . 121.6 no
C16 . C15 . H151 . 118.3 no
C15 . C16 . C17 . 119.9(2) yes
C15 . C16 . H161 . 120.4 no
C17 . C16 . H161 . 119.7 no
C16 . C17 . C18 . 120.7(2) yes
C16 . C17 . H171 . 119.8 no
C18 . C17 . H171 . 119.4 no
C13 . C18 . C17 . 119.41(18) yes
C13 . C18 . C19 . 119.55(17) yes
C17 . C18 . C19 . 120.98(18) yes
C18 . C19 . N20 . 112.96(16) yes
C18 . C19 . H191 . 109.5 no
N20 . C19 . H191 . 109.1 no
C18 . C19 . H192 . 107.0 no
N20 . C19 . H192 . 109.2 no
H191 . C19 . H192 . 108.9 no
C19 . N20 . C21 . 115.80(17) yes
C19 . N20 . C24 . 123.05(16) yes
C21 . N20 . C24 . 121.15(18) yes
N20 . C21 . C22 . 122.6(2) yes
N20 . C21 . H211 . 117.2 no
C22 . C21 . H211 . 120.2 no
C21 . C22 . C23 . 119.0(2) yes
C21 . C22 . H221 . 119.1 no
C23 . C22 . H221 . 121.9 no
C22 . C23 . C25 . 120.3(2) yes
C22 . C23 . H231 . 120.2 no
C25 . C23 . H231 . 119.5 no
N20 . C24 . C25 . 117.53(17) yes
N20 . C24 . C29 . 124.02(17) yes
C25 . C24 . C29 . 118.43(18) yes
C24 . C25 . C23 . 119.42(19) yes
C24 . C25 . C26 . 120.41(19) yes
C23 . C25 . C26 . 120.17(19) yes
C25 . C26 . C27 . 119.8(2) yes
C25 . C26 . H261 . 119.3 no
C27 . C26 . H261 . 120.9 no
C26 . C27 . C28 . 120.3(2) yes
C26 . C27 . H271 . 120.7 no
C28 . C27 . H271 . 119.0 no
C27 . C28 . C29 . 122.19(19) yes
C27 . C28 . H281 . 123.5 no
C29 . C28 . H281 . 114.3 no
C24 . C29 . C28 . 118.86(18) yes
C24 . C29 . O30 . 119.37(18) yes
C28 . C29 . O30 . 121.77(18) yes
C29 . O30 . H301 . 105(2) no
C52 . O51 . H511 . 115(2) no
O51 . C52 . C53 . 121.37(19) yes
O51 . C52 . C57 . 119.18(18) yes
C53 . C52 . C57 . 119.43(19) yes
C52 . C53 . C54 . 122.0(2) yes
C52 . C53 . H531 . 119.0 no
C54 . C53 . H531 . 119.0 no
C53 . C54 . C55 . 120.2(2) yes
C53 . C54 . H541 . 119.1 no
C55 . C54 . H541 . 120.7 no
C54 . C55 . C56 . 119.9(2) yes
C54 . C55 . H551 . 122.4 no
C56 . C55 . H551 . 117.7 no
C55 . C56 . C57 . 120.33(19) yes
C55 . C56 . C58 . 120.4(2) yes
C57 . C56 . C58 . 119.2(2) yes
C56 . C57 . C52 . 118.10(19) yes
C56 . C57 . N61 . 117.63(18) yes
C52 . C57 . N61 . 124.26(18) yes
C56 . C58 . C59 . 120.4(2) yes
C56 . C58 . H581 . 119.7 no
C59 . C58 . H581 . 119.9 no
C58 . C59 . C60 . 119.1(2) yes
C58 . C59 . H591 . 120.1 no
C60 . C59 . H591 . 120.8 no
C59 . C60 . N61 . 122.6(2) yes
C59 . C60 . H601 . 118.5 no
N61 . C60 . H601 . 118.8 no
C57 . N61 . C60 . 120.95(19) yes
C57 . N61 . C62 . 122.94(16) yes
C60 . N61 . C62 . 116.09(18) yes
N61 . C62 . C63 . 112.50(16) yes
N61 . C62 . H621 . 110.3 no
C63 . C62 . H621 . 105.2 no
N61 . C62 . H622 . 109.6 no
C63 . C62 . H622 . 109.3 no
H621 . C62 . H622 . 109.9 no
C62 . C63 . C64 . 120.03(19) yes
C62 . C63 . C68 . 120.73(18) yes
C64 . C63 . C68 . 119.16(19) yes
C63 . C64 . C65 . 121.1(2) yes
C63 . C64 . H641 . 116.1 no
C65 . C64 . H641 . 122.8 no
C64 . C65 . C66 . 119.9(2) yes
C64 . C65 . H651 . 119.9 no
C66 . C65 . H651 . 120.1 no
C65 . C66 . C67 . 119.9(2) yes
C65 . C66 . H661 . 121.7 no
C67 . C66 . H661 . 118.4 no
C66 . C67 . C68 . 120.7(2) yes
C66 . C67 . H671 . 120.1 no
C68 . C67 . H671 . 119.3 no
C63 . C68 . C67 . 119.4(2) yes
C63 . C68 . C69 . 120.09(19) yes
C67 . C68 . C69 . 120.5(2) yes
C68 . C69 . N70 . 114.03(18) yes
C68 . C69 . H691 . 108.0 no
N70 . C69 . H691 . 107.5 no
C68 . C69 . H692 . 109.0 no
N70 . C69 . H692 . 107.7 no
H691 . C69 . H692 . 110.6 no
C69 . N70 . C71 . 115.5(2) yes
C69 . N70 . C74 . 123.20(19) yes
C71 . N70 . C74 . 121.2(2) yes
N70 . C71 . C72 . 122.5(3) yes
N70 . C71 . H711 . 117.1 no
C72 . C71 . H711 . 120.2 no
C71 . C72 . C73 . 119.1(3) yes
C71 . C72 . H721 . 120.5 no
C73 . C72 . H721 . 120.3 no
C72 . C73 . C75 . 120.4(3) yes
C72 . C73 . H731 . 121.3 no
C75 . C73 . H731 . 118.3 no
N70 . C74 . C75 . 116.9(2) yes
N70 . C74 . C79 . 124.5(2) yes
C75 . C74 . C79 . 118.6(2) yes
C74 . C75 . C73 . 119.8(2) yes
C74 . C75 . C76 . 119.5(3) yes
C73 . C75 . C76 . 120.7(3) yes
C75 . C76 . C77 . 120.2(4) yes
C75 . C76 . H761 . 118.5 no
C77 . C76 . H761 . 121.3 no
C76 . C77 . C78 . 120.1(3) yes
C76 . C77 . H771 . 121.6 no
C78 . C77 . H771 . 118.4 no
C77 . C78 . C79 . 122.4(3) yes
C77 . C78 . H781 . 117.9 no
C79 . C78 . H781 . 119.7 no
C74 . C79 . C78 . 119.1(3) yes
C74 . C79 . O80 . 119.4(2) yes
C78 . C79 . O80 . 121.5(3) yes
C79 . O80 . H801 . 104(3) no
F102 . P101 . F103 . 88.85(12) yes
F102 . P101 . F104 . 89.10(13) yes
F103 . P101 . F104 . 89.87(11) yes
F102 . P101 . F105 . 91.77(13) yes
F103 . P101 . F105 . 178.86(12) yes
F104 . P101 . F105 . 89.18(11) yes
F102 . P101 . F106 . 92.83(17) yes
F103 . P101 . F106 . 88.73(12) yes
F104 . P101 . F106 . 177.59(15) yes
F105 . P101 . F106 . 92.19(11) yes
F102 . P101 . F107 . 176.84(15) yes
F103 . P101 . F107 . 89.64(11) yes
F104 . P101 . F107 . 88.12(13) yes
F105 . P101 . F107 . 89.69(12) yes
F106 . P101 . F107 . 89.91(18) yes
F112 . P111 . F113 . 90.39(14) yes
F112 . P111 . F114 . 90.47(15) yes
F113 . P111 . F114 . 91.52(11) yes
F112 . P111 . F115 . 89.81(15) yes
F113 . P111 . F115 . 179.77(12) yes
F114 . P111 . F115 . 88.60(11) yes
F112 . P111 . F116 . 89.64(14) yes
F113 . P111 . F116 . 89.58(11) yes
F114 . P111 . F116 . 178.89(11) yes
F115 . P111 . F116 . 90.30(11) yes
F112 . P111 . F117 . 179.00(16) yes
F113 . P111 . F117 . 89.49(14) yes
F114 . P111 . F117 . 90.52(16) yes
F115 . P111 . F117 . 90.31(15) yes
F116 . P111 . F117 . 89.37(15) yes
F122 . P121 . F123 . 88.80(13) yes
F122 . P121 . F124 . 92.31(15) yes
F123 . P121 . F124 . 88.92(15) yes
F122 . P121 . F125 . 88.84(13) yes
F123 . P121 . F125 . 177.43(14) yes
F124 . P121 . F125 . 90.16(13) yes
F122 . P121 . F126 . 89.65(14) yes
F123 . P121 . F126 . 90.89(16) yes
F124 . P121 . F126 . 178.03(15) yes
F125 . P121 . F126 . 90.12(14) yes
F122 . P121 . F127 . 179.07(14) yes
F123 . P121 . F127 . 90.88(14) yes
F124 . P121 . F127 . 88.56(14) yes
F125 . P121 . F127 . 91.49(14) yes
F126 . P121 . F127 . 89.48(13) yes
F134 . P131 . F137 . 90.9(2) yes
F134 . P131 . F133 . 89.2(3) yes
F137 . P131 . F133 . 89.0(3) yes
F134 . P131 . F132 . 88.5(2) yes
F137 . P131 . F132 . 179.39(13) yes
F133 . P131 . F132 . 91.0(3) yes
F134 . P131 . F135 . 88.8(3) yes
F137 . P131 . F135 . 88.3(3) yes
F133 . P131 . F135 . 176.7(4) yes
F132 . P131 . F135 . 91.7(3) yes
F134 . P131 . F136 . 176.5(4) yes
F137 . P131 . F136 . 85.6(3) yes
F133 . P131 . F136 . 91.0(3) yes
F132 . P131 . F136 . 95.0(3) yes
F135 . P131 . F136 . 90.8(3) yes
N201 . C202 . C203 . 179.1(5) yes
C202 . C203 . H2031 . 108.8 no
C202 . C203 . H2033 . 108.7 no
H2031 . C203 . H2033 . 112.4 no
C202 . C203 . H2032 . 107.6 no
H2031 . C203 . H2032 . 109.9 no
H2033 . C203 . H2032 . 109.3 no
N211 . C212 . C213 . 179.3(3) yes
C212 . C213 . H2133 . 108.7 no
C212 . C213 . H2132 . 110.5 no
H2133 . C213 . H2132 . 109.9 no
C212 . C213 . H2131 . 110.8 no
H2133 . C213 . H2131 . 109.4 no
H2132 . C213 . H2131 . 107.6 no
N221 . C222 . C223 . 176.4(5) yes
C222 . C223 . H2231 . 109.2 no
C222 . C223 . H2232 . 109.1 no
H2231 . C223 . H2232 . 109.5 no
C222 . C223 . H2233 . 110.1 no
H2231 . C223 . H2233 . 109.5 no
H2232 . C223 . H2233 . 109.5 no
N224 . C225 . C226 . 179.6(3) yes
C225 . C226 . H2262 . 115.1 no
C225 . C226 . H2261 . 110.8 no
H2262 . C226 . H2261 . 107.0 no
C225 . C226 . H2263 . 110.1 no
H2262 . C226 . H2263 . 108.9 no
H2261 . C226 . H2263 . 104.4 no
N241 . C242 . C243 . 177.8(5) yes
C242 . C243 . H2431 . 112.1 no
C242 . C243 . H2433 . 107.4 no
H2431 . C243 . H2433 . 108.7 no
C242 . C243 . H2432 . 107.9 no
H2431 . C243 . H2432 . 111.3 no
H2433 . C243 . H2432 . 109.4 no
N251 . C252 . C253 . 178.2(6) yes
C252 . C253 . H2531 . 110.3 no
C252 . C253 . H2533 . 111.7 no
H2531 . C253 . H2533 . 111.0 no
C252 . C253 . H2532 . 110.9 no
H2531 . C253 . H2532 . 107.3 no
H2533 . C253 . H2532 . 105.5 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
C60 . H601 . N201 2_566 130.6(2) 0.935 2.516 3.204(4) yes
O30 . H301 . N211 . 165(3) 0.831 1.899 2.710(4) yes
O1 . H11 . N221 . 173(4) 0.794 2.026 2.816(4) yes
O51 . H511 . N224 . 177(3) 0.816 1.907 2.722(4) yes
O80 . H801 . N251 2_566 168(4) 0.803 1.998 2.787(4) yes

_iucr_refine_instructions_details_constraints 
;
#
# Punched on 26/05/16 at 16:51:49
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT O    (    1 ,X'S,U'S)  UNTIL C    (  253 ) 
CONT H    (  301 ,X'S)  UNTIL H    (  801 ) 
CONT F    (  146 ,X'S,U'S)  UNTIL F    (  143 ) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) 
RIDE C   (  60,X'S) H   ( 601,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) H   ( 622,X'S) 
RIDE C   (  64,X'S) H   ( 641,X'S) 
RIDE C   (  65,X'S) H   ( 651,X'S) 
RIDE C   (  66,X'S) H   ( 661,X'S) 
RIDE C   (  67,X'S) H   ( 671,X'S) 
RIDE C   (  69,X'S) H   ( 691,X'S) H   ( 692,X'S) 
RIDE C   (  71,X'S) H   ( 711,X'S) 
RIDE C   (  72,X'S) H   ( 721,X'S) 
RIDE C   (  73,X'S) H   ( 731,X'S) 
RIDE C   (  76,X'S) H   ( 761,X'S) 
RIDE C   (  77,X'S) H   ( 771,X'S) 
RIDE C   (  78,X'S) H   ( 781,X'S) 
RIDE C   ( 203,X'S) H   (2031,X'S) H   (2033,X'S) H   (2032,X'S) 
RIDE C   ( 213,X'S) H   (2133,X'S) H   (2132,X'S) H   (2131,X'S) 
RIDE C   ( 223,X'S) H   (2231,X'S) H   (2232,X'S) H   (2233,X'S) 
RIDE C   ( 226,X'S) H   (2262,X'S) H   (2261,X'S) H   (2263,X'S) 
RIDE C   ( 243,X'S) H   (2431,X'S) H   (2433,X'S) H   (2432,X'S) 
RIDE C   ( 253,X'S) H   (2531,X'S) H   (2533,X'S) H   (2532,X'S) 
END         
;

_iucr_refine_instructions_details_restraints 
;                                                                   
#
# Punched on 26/05/16 at 16:51:49
#
#LIST     16                                                                    
DIST 0, 0.01 = MEAN P(131) TO F(132), P(131) TO F(137) 
CONT P(131) TO F(133), P(131) TO F(134) 
CONT P(131) TO F(135), P(131) TO F(136) 
CONT P(131) TO F(143), P(131) TO F(144) 
CONT P(131) TO F(145), P(131) TO F(146) 
ANGL 90, 1 = F(132) TO P(131) TO F(133) 
CONT F(132) TO P(131) TO F(134) 
CONT F(132) TO P(131) TO F(135) 
CONT F(132) TO P(131) TO F(136) 
CONT F(137) TO P(131) TO F(133) 
CONT F(137) TO P(131) TO F(134) 
CONT F(137) TO P(131) TO F(135) 
CONT F(137) TO P(131) TO F(136) 
CONT F(133) TO P(131) TO F(134) 
CONT F(134) TO P(131) TO F(135) 
CONT F(135) TO P(131) TO F(136) 
CONT F(136) TO P(131) TO F(133) 
CONT F(132) TO P(131) TO F(143) 
CONT F(132) TO P(131) TO F(144) 
CONT F(132) TO P(131) TO F(145) 
CONT F(132) TO P(131) TO F(146) 
CONT F(137) TO P(131) TO F(143) 
CONT F(137) TO P(131) TO F(144) 
CONT F(137) TO P(131) TO F(145) 
CONT F(137) TO P(131) TO F(146) 
CONT F(143) TO P(131) TO F(144) 
CONT F(144) TO P(131) TO F(145) 
CONT F(145) TO P(131) TO F(146) 
CONT F(146) TO P(131) TO F(143) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 1) TO H(11) 
REST 0.060, 0.002 = H(11,U[ISO]) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 30) TO H(301) 
REST 0.050, 0.002 = H(301,U[ISO]) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 51) TO H(511) 
REST 0.049, 0.002 = H(511,U[ISO]) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 80) TO H(801) 
REST 0.082, 0.002 = H(801,U[ISO]) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00200 = P(131) TO F(134) 
VIBR .0, 0.00200 = P(131) TO F(137) 
VIBR .0, 0.00200 = P(131) TO F(133) 
VIBR .0, 0.00200 = P(131) TO F(132) 
VIBR .0, 0.00200 = P(131) TO F(135) 
VIBR .0, 0.00200 = P(131) TO F(136) 
VIBR .0, 0.00500 = F(137) TO F(134) 
VIBR .0, 0.00500 = F(133) TO F(134) 
VIBR .0, 0.00500 = F(133) TO F(137) 
VIBR .0, 0.00500 = F(132) TO F(134) 
VIBR .0, 0.00500 = F(132) TO F(137) 
VIBR .0, 0.00500 = F(132) TO F(133) 
VIBR .0, 0.00500 = F(135) TO F(134) 
VIBR .0, 0.00500 = F(135) TO F(137) 
VIBR .0, 0.00500 = F(135) TO F(133) 
VIBR .0, 0.00500 = F(135) TO F(132) 
VIBR .0, 0.00500 = F(136) TO F(134) 
VIBR .0, 0.00500 = F(136) TO F(137) 
VIBR .0, 0.00500 = F(136) TO F(133) 
VIBR .0, 0.00500 = F(136) TO F(132) 
VIBR .0, 0.00500 = F(136) TO F(135) 
VIBR .0, 0.00200 = P(131) TO F(144) 
VIBR .0, 0.00200 = P(131) TO F(143) 
VIBR .0, 0.00200 = P(131) TO F(145) 
VIBR .0, 0.00200 = P(131) TO F(146) 
VIBR .0, 0.00500 = F(143) TO F(144) 
VIBR .0, 0.00500 = F(145) TO F(144) 
VIBR .0, 0.00500 = F(145) TO F(143) 
VIBR .0, 0.00500 = F(146) TO F(144) 
VIBR .0, 0.00500 = F(146) TO F(143) 
VIBR .0, 0.00500 = F(146) TO F(145) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.08000 = P(131) TO F(134) 
U(IJ) .0, 0.08000 = P(131) TO F(137) 
U(IJ) .0, 0.08000 = P(131) TO F(133) 
U(IJ) .0, 0.08000 = P(131) TO F(132) 
U(IJ) .0, 0.08000 = P(131) TO F(135) 
U(IJ) .0, 0.08000 = P(131) TO F(146) 
U(IJ) .0, 0.08000 = P(131) TO F(144) 
U(IJ) .0, 0.08000 = P(131) TO F(143) 
U(IJ) .0, 0.08000 = P(131) TO F(145) 
REM   THERMSIM   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
3 -2 3 x .
####################################################################### 
# 
# 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_3Cl
_database_code_depnum_ccdc_archive 'CCDC 2050544'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
The asymmetric unit cell contains the bis-quinolinium dication, one PF6 anion,
one chloride anion and one acetonitrile solvate located on a symmetry position.

C-H hydrogen atoms were generally visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. O-H hydrogen 
atoms were visible in the Fourier difference map and were refined
with restraints on bond lengths and angles. 

Other than this, it was not necessary to use any crystallographic restraints.
;

_cell_length_a                   44.058(12)
_cell_length_b                   8.6635(3)
_cell_length_c                   24.582(7)
_cell_angle_alpha                90
_cell_angle_beta                 146.85(6)
_cell_angle_gamma                90
_cell_volume                     5130.9(15)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c '
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
x,-y,z+1/2
-x,y,-z+1/2
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 0.0181 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'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            8

_chemical_formula_sum            'C27 H23.50 Cl1 F6 N2.50 O2 P1'
_chemical_formula_moiety         'C26 H22 N2 O2, Cl, F6 P, 0.5(C2 H3 N)'
_chemical_compound_source        synthesized
_chemical_formula_weight         595.41


_cell_measurement_reflns_used    9555
_cell_measurement_theta_min      4
_cell_measurement_theta_max      72
_cell_measurement_temperature    150

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.07
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_max          0.40

_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2439.989
_exptl_absorpt_coefficient_mu    2.587

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_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            26379
_reflns_number_total             5081
_diffrn_reflns_av_R_equivalents  0.034

_diffrn_reflns_theta_min         3.669
_diffrn_reflns_theta_max         72.472
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        72.472
_diffrn_measured_fraction_theta_full 0.996

_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_reflns_limit_h_min              -54
_reflns_limit_h_max              29
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              30

_oxford_diffrn_Wilson_B_factor   2.95
_oxford_diffrn_Wilson_scale      0.16

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.58
_refine_diff_density_max         0.46

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         5078
_refine_ls_number_restraints     4
_refine_ls_number_parameters     366
_oxford_refine_ls_R_factor_ref   0.0499
_refine_ls_wR_factor_ref         0.1100
_refine_ls_goodness_of_fit_ref   0.9409
_refine_ls_shift/su_max          0.0050760
_refine_ls_shift/su_mean         0.0000547

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5078
_refine_ls_R_factor_all          0.0499
_refine_ls_wR_factor_all         0.1100

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4648
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_gt          0.1066

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, 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: 
 0.193E+04 0.321E+04 0.195E+04 806. 177. 
;

# 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
O1 O 0.47837(7) 0.2196(2) 0.45003(12) 0.0420 1.0000 Uani D . . . . .
C2 C 0.43517(8) 0.1394(2) 0.36540(15) 0.0313 1.0000 Uani . . . . . .
C3 C 0.40491(9) 0.0392(3) 0.35176(16) 0.0347 1.0000 Uani . . . . . .
C4 C 0.36025(10) -0.0460(3) 0.26430(18) 0.0411 1.0000 Uani . . . . . .
C5 C 0.34602(9) -0.0351(3) 0.18945(18) 0.0401 1.0000 Uani . . . . . .
C6 C 0.37603(8) 0.0640(2) 0.20009(15) 0.0321 1.0000 Uani . . . . . .
C7 C 0.42024(8) 0.1572(2) 0.28673(15) 0.0292 1.0000 Uani . . . . . .
C8 C 0.36285(9) 0.0724(3) 0.12420(16) 0.0411 1.0000 Uani . . . . . .
C9 C 0.39046(10) 0.1722(3) 0.13215(17) 0.0438 1.0000 Uani . . . . . .
C10 C 0.43159(10) 0.2649(3) 0.21617(17) 0.0394 1.0000 Uani . . . . . .
N11 N 0.44645(7) 0.2576(2) 0.29043(13) 0.0315 1.0000 Uani . . . . . .
C12 C 0.49256(9) 0.3629(2) 0.37573(16) 0.0321 1.0000 Uani . . . . . .
C13 C 0.54904(8) 0.2866(2) 0.45704(15) 0.0286 1.0000 Uani . . . . . .
C14 C 0.55684(9) 0.1424(2) 0.44572(16) 0.0325 1.0000 Uani . . . . . .
C15 C 0.60927(9) 0.0779(2) 0.52020(17) 0.0343 1.0000 Uani . . . . . .
C16 C 0.65468(9) 0.1577(3) 0.60751(17) 0.0355 1.0000 Uani . . . . . .
C17 C 0.64790(9) 0.3027(3) 0.62074(16) 0.0332 1.0000 Uani . . . . . .
C18 C 0.59560(8) 0.3677(2) 0.54678(15) 0.0275 1.0000 Uani . . . . . .
C19 C 0.58603(8) 0.5281(2) 0.55501(15) 0.0307 1.0000 Uani . . . . . .
N20 N 0.63589(7) 0.59719(19) 0.65595(13) 0.0299 1.0000 Uani . . . . . .
C21 C 0.66448(10) 0.6954(3) 0.6678(2) 0.0394 1.0000 Uani . . . . . .
C22 C 0.71204(11) 0.7702(3) 0.7572(2) 0.0444 1.0000 Uani . . . . . .
C23 C 0.72995(10) 0.7439(3) 0.83548(19) 0.0435 1.0000 Uani . . . . . .
C24 C 0.65247(8) 0.5650(2) 0.73378(15) 0.0281 1.0000 Uani . . . . . .
C25 C 0.70081(9) 0.6408(2) 0.82605(16) 0.0336 1.0000 Uani . . . . . .
C26 C 0.71891(10) 0.6145(3) 0.90688(17) 0.0438 1.0000 Uani . . . . . .
C27 C 0.69028(10) 0.5175(3) 0.89721(18) 0.0449 1.0000 Uani . . . . . .
C28 C 0.64285(10) 0.4419(3) 0.80711(17) 0.0366 1.0000 Uani . . . . . .
C29 C 0.62338(8) 0.4620(2) 0.72570(15) 0.0303 1.0000 Uani . . . . . .
O30 O 0.57791(7) 0.38914(19) 0.63951(12) 0.0376 1.0000 Uani D . . . . .
P101 P 0.68312(3) 0.68041(9) 0.53702(5) 0.0530 1.0000 Uani . . . . . .
F102 F 0.69484(11) 0.8542(3) 0.5713(2) 0.1070 1.0000 Uani . . . . . .
F103 F 0.64728(9) 0.7346(2) 0.43285(15) 0.0746 1.0000 Uani . . . . . .
F104 F 0.73627(9) 0.6788(4) 0.57990(19) 0.1099 1.0000 Uani . . . . . .
F105 F 0.71862(9) 0.6244(4) 0.64098(15) 0.1126 1.0000 Uani . . . . . .
F106 F 0.62906(7) 0.6857(3) 0.49307(13) 0.0746 1.0000 Uani . . . . . .
F107 F 0.67026(11) 0.5071(2) 0.50162(19) 0.0896 1.0000 Uani . . . . . .
N201 N 0.5000 0.5251(4) 0.2500 0.0702 1.0000 Uani S T . . . .
C202 C 0.5000 0.6569(5) 0.2500 0.0494 1.0000 Uani S T . . . .
C203 C 0.500000(10) 0.8230(5) 0.250000(10) 0.0591 1.0000 Uani S T . . . .
Cl1 Cl 0.511932(18) 0.20055(5) 0.61953(3) 0.0266 1.0000 Uani . . . . . .
H31 H 0.4151 0.0276 0.4048 0.0435 1.0000 Uiso R . . . . .
H41 H 0.3400 -0.1124 0.2584 0.0530 1.0000 Uiso R . . . . .
H51 H 0.3156 -0.0961 0.1287 0.0486 1.0000 Uiso R . . . . .
H81 H 0.3341 0.0050 0.0672 0.0516 1.0000 Uiso R . . . . .
H91 H 0.3829 0.1795 0.0826 0.0539 1.0000 Uiso R . . . . .
H101 H 0.4515 0.3391 0.2243 0.0509 1.0000 Uiso R . . . . .
H121 H 0.4910 0.4549 0.3501 0.0397 1.0000 Uiso R . . . . .
H122 H 0.4864 0.3913 0.4048 0.0383 1.0000 Uiso R . . . . .
H141 H 0.5254 0.0861 0.3861 0.0419 1.0000 Uiso R . . . . .
H151 H 0.6143 -0.0221 0.5113 0.0414 1.0000 Uiso R . . . . .
H161 H 0.6910 0.1130 0.6594 0.0436 1.0000 Uiso R . . . . .
H171 H 0.6796 0.3589 0.6821 0.0416 1.0000 Uiso R . . . . .
H191 H 0.5757 0.5989 0.5095 0.0386 1.0000 Uiso R . . . . .
H192 H 0.5556 0.5243 0.5369 0.0383 1.0000 Uiso R . . . . .
H211 H 0.6506 0.7092 0.6107 0.0481 1.0000 Uiso R . . . . .
H221 H 0.7308 0.8398 0.7618 0.0555 1.0000 Uiso R . . . . .
H231 H 0.7625 0.7936 0.8972 0.0545 1.0000 Uiso R . . . . .
H261 H 0.7516 0.6664 0.9687 0.0527 1.0000 Uiso R . . . . .
H271 H 0.7028 0.5019 0.9527 0.0558 1.0000 Uiso R . . . . .
H281 H 0.6229 0.3742 0.8014 0.0447 1.0000 Uiso R . . . . .
H11 H 0.4827(14) 0.200(4) 0.490(2) 0.0664 1.0000 Uiso D . . . . .
H301 H 0.5631(12) 0.334(3) 0.641(2) 0.0601 1.0000 Uiso D . . . . .
H2031 H 0.5264 0.8595 0.2641 0.0725 0.5000 Uiso R . . . . .
H2032 H 0.4641 0.8595 0.1866 0.0725 0.5000 Uiso R . . . . .
H2033 H 0.5094 0.8595 0.2994 0.0725 0.5000 Uiso R . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.280(14)

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 . C2 . 1.342(3) yes
O1 . H11 . 0.840(17) no
C2 . C3 . 1.377(3) yes
C2 . C7 . 1.437(3) yes
C3 . C4 . 1.399(4) yes
C3 . H31 . 0.965 no
C4 . C5 . 1.362(4) yes
C4 . H41 . 0.966 no
C5 . C6 . 1.405(3) yes
C5 . H51 . 0.977 no
C6 . C7 . 1.427(3) yes
C6 . C8 . 1.417(3) yes
C7 . N11 . 1.386(3) yes
C8 . C9 . 1.367(4) yes
C8 . H81 . 0.967 no
C9 . C10 . 1.388(4) yes
C9 . H91 . 0.959 no
C10 . N11 . 1.328(3) yes
C10 . H101 . 0.966 no
N11 . C12 . 1.491(3) yes
C12 . C13 . 1.515(3) yes
C12 . H121 . 0.981 no
C12 . H122 . 0.984 no
C13 . C14 . 1.385(3) yes
C13 . C18 . 1.411(3) yes
C14 . C15 . 1.385(4) yes
C14 . H141 . 0.952 no
C15 . C16 . 1.377(4) yes
C15 . H151 . 0.964 no
C16 . C17 . 1.392(3) yes
C16 . H161 . 0.959 no
C17 . C18 . 1.385(3) yes
C17 . H171 . 0.967 no
C18 . C19 . 1.514(3) yes
C19 . N20 . 1.488(3) yes
C19 . H191 . 0.990 no
C19 . H192 . 0.997 no
N20 . C21 . 1.334(3) yes
N20 . C24 . 1.390(3) yes
C21 . C22 . 1.389(4) yes
C21 . H211 . 0.960 no
C22 . C23 . 1.355(4) yes
C22 . H221 . 0.951 no
C23 . C25 . 1.414(3) yes
C23 . H231 . 0.949 no
C24 . C25 . 1.423(3) yes
C24 . C29 . 1.432(3) yes
C25 . C26 . 1.408(3) yes
C26 . C27 . 1.360(4) yes
C26 . H261 . 0.960 no
C27 . C28 . 1.397(4) yes
C27 . H271 . 0.962 no
C28 . C29 . 1.377(3) yes
C28 . H281 . 0.963 no
C29 . O30 . 1.339(3) yes
O30 . H301 . 0.839(17) no
P101 . F102 . 1.586(2) yes
P101 . F103 . 1.581(2) yes
P101 . F104 . 1.569(2) yes
P101 . F105 . 1.587(3) yes
P101 . F106 . 1.592(2) yes
P101 . F107 . 1.583(2) yes
N201 . C202 . 1.141(5) yes
C202 . C203 . 1.439(5) yes
C203 . H2031 6_655 0.950 no
C203 . H2032 6_655 0.950 no
C203 . H2033 6_655 0.950 no
C203 . H2031 . 0.950 no
C203 . H2032 . 0.950 no
C203 . H2033 . 0.950 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . H11 . 110(2) no
O1 . C2 . C3 . 122.1(2) yes
O1 . C2 . C7 . 119.18(19) yes
C3 . C2 . C7 . 118.8(2) yes
C2 . C3 . C4 . 122.5(2) yes
C2 . C3 . H31 . 118.5 no
C4 . C3 . H31 . 119.0 no
C3 . C4 . C5 . 120.3(2) yes
C3 . C4 . H41 . 118.7 no
C5 . C4 . H41 . 121.1 no
C4 . C5 . C6 . 119.6(2) yes
C4 . C5 . H51 . 121.1 no
C6 . C5 . H51 . 119.3 no
C5 . C6 . C7 . 121.3(2) yes
C5 . C6 . C8 . 120.1(2) yes
C7 . C6 . C8 . 118.6(2) yes
C2 . C7 . C6 . 117.5(2) yes
C2 . C7 . N11 . 124.1(2) yes
C6 . C7 . N11 . 118.31(19) yes
C6 . C8 . C9 . 120.6(2) yes
C6 . C8 . H81 . 118.2 no
C9 . C8 . H81 . 121.2 no
C8 . C9 . C10 . 118.4(2) yes
C8 . C9 . H91 . 122.7 no
C10 . C9 . H91 . 118.9 no
C9 . C10 . N11 . 123.0(2) yes
C9 . C10 . H101 . 121.4 no
N11 . C10 . H101 . 115.6 no
C7 . N11 . C10 . 121.0(2) yes
C7 . N11 . C12 . 123.75(17) yes
C10 . N11 . C12 . 115.3(2) yes
N11 . C12 . C13 . 112.78(19) yes
N11 . C12 . H121 . 108.3 no
C13 . C12 . H121 . 110.9 no
N11 . C12 . H122 . 107.1 no
C13 . C12 . H122 . 107.3 no
H121 . C12 . H122 . 110.4 no
C12 . C13 . C14 . 122.6(2) yes
C12 . C13 . C18 . 118.5(2) yes
C14 . C13 . C18 . 118.89(19) yes
C13 . C14 . C15 . 121.2(2) yes
C13 . C14 . H141 . 119.0 no
C15 . C14 . H141 . 119.7 no
C14 . C15 . C16 . 119.8(2) yes
C14 . C15 . H151 . 120.6 no
C16 . C15 . H151 . 119.6 no
C15 . C16 . C17 . 120.1(2) yes
C15 . C16 . H161 . 120.0 no
C17 . C16 . H161 . 119.9 no
C16 . C17 . C18 . 120.5(2) yes
C16 . C17 . H171 . 120.4 no
C18 . C17 . H171 . 119.1 no
C13 . C18 . C17 . 119.5(2) yes
C13 . C18 . C19 . 117.6(2) yes
C17 . C18 . C19 . 122.8(2) yes
C18 . C19 . N20 . 113.85(16) yes
C18 . C19 . H191 . 109.5 no
N20 . C19 . H191 . 106.0 no
C18 . C19 . H192 . 109.2 no
N20 . C19 . H192 . 108.3 no
H191 . C19 . H192 . 109.9 no
C19 . N20 . C21 . 115.26(19) yes
C19 . N20 . C24 . 123.75(17) yes
C21 . N20 . C24 . 121.0(2) yes
N20 . C21 . C22 . 122.8(2) yes
N20 . C21 . H211 . 115.5 no
C22 . C21 . H211 . 121.7 no
C21 . C22 . C23 . 118.8(2) yes
C21 . C22 . H221 . 119.7 no
C23 . C22 . H221 . 121.6 no
C22 . C23 . C25 . 120.3(2) yes
C22 . C23 . H231 . 120.0 no
C25 . C23 . H231 . 119.8 no
N20 . C24 . C25 . 117.5(2) yes
N20 . C24 . C29 . 123.79(19) yes
C25 . C24 . C29 . 118.70(19) yes
C24 . C25 . C23 . 119.7(2) yes
C24 . C25 . C26 . 119.9(2) yes
C23 . C25 . C26 . 120.4(2) yes
C25 . C26 . C27 . 120.4(2) yes
C25 . C26 . H261 . 118.9 no
C27 . C26 . H261 . 120.7 no
C26 . C27 . C28 . 120.3(2) yes
C26 . C27 . H271 . 119.5 no
C28 . C27 . H271 . 120.2 no
C27 . C28 . C29 . 122.0(2) yes
C27 . C28 . H281 . 119.2 no
C29 . C28 . H281 . 118.8 no
C24 . C29 . C28 . 118.7(2) yes
C24 . C29 . O30 . 119.52(19) yes
C28 . C29 . O30 . 121.7(2) yes
C29 . O30 . H301 . 113(2) no
F102 . P101 . F103 . 91.03(16) yes
F102 . P101 . F104 . 90.72(16) yes
F103 . P101 . F104 . 89.75(18) yes
F102 . P101 . F105 . 89.49(19) yes
F103 . P101 . F105 . 179.35(16) yes
F104 . P101 . F105 . 90.64(16) yes
F102 . P101 . F106 . 88.26(13) yes
F103 . P101 . F106 . 89.68(14) yes
F104 . P101 . F106 . 178.82(16) yes
F105 . P101 . F106 . 89.94(16) yes
F102 . P101 . F107 . 178.86(14) yes
F103 . P101 . F107 . 88.80(12) yes
F104 . P101 . F107 . 90.41(15) yes
F105 . P101 . F107 . 90.67(15) yes
F106 . P101 . F107 . 90.61(14) yes
N201 . C202 . C203 . 179.992 yes
C202 . C203 . H2031 6_655 109.5 no
C202 . C203 . H2032 6_655 109.5 no
H2031 6_655 C203 . H2032 6_655 109.5 no
C202 . C203 . H2033 6_655 109.5 no
H2031 6_655 C203 . H2033 6_655 109.5 no
H2032 6_655 C203 . H2033 6_655 109.5 no
C202 . C203 . H2031 . 109.5 no
H2031 6_655 C203 . H2031 . 141.1 no
H2032 6_655 C203 . H2031 . 56.3 no
H2033 6_655 C203 . H2031 . 56.3 no
C202 . C203 . H2032 . 109.5 no
H2031 6_655 C203 . H2032 . 56.3 no
H2032 6_655 C203 . H2032 . 141.1 no
H2033 6_655 C203 . H2032 . 56.3 no
H2031 . C203 . H2032 . 109.5 no
C202 . C203 . H2033 . 109.5 no
H2031 6_655 C203 . H2033 . 56.3 no
H2032 6_655 C203 . H2033 . 56.3 no
H2033 6_655 C203 . H2033 . 141.1 no
H2031 . C203 . H2033 . 109.5 no
H2032 . C203 . H2033 . 109.5 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
C10 . H101 . N201 . 176.30(7) 0.966 2.301 3.265(5) yes

_iucr_refine_instructions_details_constraints 
;
#
# Punched on 25/04/16 at 17:50:31
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT O    (    1 ,X'S,U'S)  UNTIL CL   (    1 ) 
CONT H    (   11 ,X'S)  UNTIL H    (  301 ) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   ( 203,X'S) H   (2031,X'S) H   (2033,X'S) H   (2032,X'S) 
END                                                                             
;

_iucr_refine_instructions_details_restraints 
;
#
# Punched on 25/04/16 at 17:50:31
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 1) TO H(11) 
REST 0.064, 0.002 = H(11,U[ISO]) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 30) TO H(301) 
REST 0.057, 0.002 = H(301,U[ISO]) 
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
-7 1 1 x .
4 0 0 x .
-12 0 4 x .
####################################################################### 
# 
# 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_3Br2
_database_code_depnum_ccdc_archive 'CCDC 2050543'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;

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

_refine_special_details          
; 
C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. O-H hydrogen atoms
were visible in the difference map and were refined with restraints on bond 
lengths and angles. Other than restraints on the O-H hydrogen atoms, it was
not necessary to use any crystallographic restraints in the refinement.
;

_cell_length_a                   7.5194(4)
_cell_length_b                   9.4830(4)
_cell_length_c                   9.4934(3)
_cell_angle_alpha                118.013(4)
_cell_angle_beta                 97.791(3)
_cell_angle_gamma                104.191(4)
_cell_volume                     553.98(5)

_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 0.0181 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'
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            1

_chemical_formula_sum            'C26 H22 Br2 N2 O2'
_chemical_formula_moiety         'C26 H22 N2 O2, 2(Br)'
_chemical_compound_source        synthesized
_chemical_formula_weight         554.28


_cell_measurement_reflns_used    5624
_cell_measurement_theta_min      5.44
_cell_measurement_theta_max      73.59
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.16
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.35

_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             278
_exptl_absorpt_coefficient_mu    4.857

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.55
_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    'Superflip (Palatinus & Chapuis, 2007)'
_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            6507
_diffrn_reflns_av_unetI/netI     0.015
_reflns_number_total             2231
_diffrn_reflns_av_R_equivalents  0.013

_diffrn_reflns_theta_min         5.452
_diffrn_reflns_theta_max         73.843
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        73.843
_diffrn_measured_fraction_theta_full 0.996

_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -11
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              11

_oxford_diffrn_Wilson_B_factor   1.71
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.38
_refine_diff_density_max         0.38

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     2
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2231
_oxford_refine_ls_R_factor_ref   0.0210
_refine_ls_R_factor_all          0.0210
_refine_ls_wR_factor_ref         0.0549
_refine_ls_wR_factor_all         0.0549
_refine_ls_goodness_of_fit_ref   1.0434
_refine_ls_shift/su_max          0.0023026
_refine_ls_shift/su_mean         0.0000569

# Computed with I/sigma = -10 
_oxford_reflns_number_all        2231
_oxford_refine_ls_R_factor_all   0.0210
_oxford_refine_ls_wR_factor_all  0.0549

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2223
_refine_ls_R_factor_gt           0.0209
_refine_ls_wR_factor_gt          0.0548


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² + 0.60P] 
 ,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
O1 O 0.33954(19) 1.22296(16) 0.96069(16) 0.0198 1.0000 Uani D . . . . .
C2 C 0.2825(2) 1.1030(2) 0.9994(2) 0.0154 1.0000 Uani . . . . . .
C3 C 0.2387(2) 1.1416(2) 1.1471(2) 0.0185 1.0000 Uani . . . . . .
C4 C 0.1846(2) 1.0189(2) 1.1910(2) 0.0207 1.0000 Uani . . . . . .
C5 C 0.1749(2) 0.8555(2) 1.0879(2) 0.0204 1.0000 Uani . . . . . .
C6 C 0.2190(2) 0.8100(2) 0.9362(2) 0.0167 1.0000 Uani . . . . . .
C7 C 0.2711(2) 0.9330(2) 0.8879(2) 0.0142 1.0000 Uani . . . . . .
C8 C 0.2173(3) 0.6430(2) 0.8328(2) 0.0212 1.0000 Uani . . . . . .
C9 C 0.2643(3) 0.5994(2) 0.6884(2) 0.0225 1.0000 Uani . . . . . .
C10 C 0.3089(2) 0.7203(2) 0.6419(2) 0.0192 1.0000 Uani . . . . . .
N11 N 0.31063(19) 0.87880(18) 0.73502(18) 0.0144 1.0000 Uani . . . . . .
C12 C 0.3508(2) 0.9880(2) 0.6598(2) 0.0150 1.0000 Uani . . . . . .
C13 C 0.1676(2) 0.9945(2) 0.5785(2) 0.0141 1.0000 Uani . . . . . .
C14 C 0.1436(2) 1.1507(2) 0.6279(2) 0.0160 1.0000 Uani . . . . . .
C15 C -0.0237(2) 1.1553(2) 0.5499(2) 0.0160 1.0000 Uani . . . . . .
Br1 Br 0.31877(3) 1.57454(2) 1.22276(2) 0.0232 1.0000 Uani . . . . . .
H31 H 0.2457 1.2544 1.2187 0.0222 1.0000 Uiso R . . . . .
H41 H 0.1550 1.0508 1.2948 0.0248 1.0000 Uiso R . . . . .
H51 H 0.1406 0.7729 1.1175 0.0244 1.0000 Uiso R . . . . .
H81 H 0.1859 0.5626 0.8672 0.0254 1.0000 Uiso R . . . . .
H91 H 0.2693 0.4902 0.6194 0.0274 1.0000 Uiso R . . . . .
H101 H 0.3384 0.6926 0.5409 0.0222 1.0000 Uiso R . . . . .
H121 H 0.4382 1.1021 0.7439 0.0170 1.0000 Uiso R . . . . .
H122 H 0.4117 0.9342 0.5730 0.0173 1.0000 Uiso R . . . . .
H141 H 0.2430 1.2536 0.7164 0.0191 1.0000 Uiso R . . . . .
H151 H -0.0391 1.2625 0.5855 0.0189 1.0000 Uiso R . . . . .
H11 H 0.337(4) 1.313(2) 1.033(3) 0.0299(19) 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          10.8(3)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.345(2) yes
O1 . H11 . 0.814(16) no
C2 . C3 . 1.382(2) yes
C2 . C7 . 1.425(2) yes
C3 . C4 . 1.401(2) yes
C3 . H31 . 0.943 no
C4 . C5 . 1.366(3) yes
C4 . H41 . 0.961 no
C5 . C6 . 1.409(3) yes
C5 . H51 . 0.942 no
C6 . C7 . 1.432(2) yes
C6 . C8 . 1.414(3) yes
C7 . N11 . 1.397(2) yes
C8 . C9 . 1.358(3) yes
C8 . H81 . 0.954 no
C9 . C10 . 1.395(3) yes
C9 . H91 . 0.945 no
C10 . N11 . 1.334(2) yes
C10 . H101 . 0.942 no
N11 . C12 . 1.507(2) yes
C12 . C13 . 1.515(2) yes
C12 . H121 . 0.968 no
C12 . H122 . 0.985 no
C13 . C15 2_576 1.392(2) yes
C13 . C14 . 1.396(2) yes
C14 . C15 . 1.392(2) yes
C14 . H141 . 0.959 no
C15 . H151 . 0.952 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 . O1 . H11 . 109.6(18) no
O1 . C2 . C3 . 121.48(16) yes
O1 . C2 . C7 . 119.50(15) yes
C3 . C2 . C7 . 119.01(16) yes
C2 . C3 . C4 . 122.00(17) yes
C2 . C3 . H31 . 117.8 no
C4 . C3 . H31 . 120.2 no
C3 . C4 . C5 . 120.37(17) yes
C3 . C4 . H41 . 119.4 no
C5 . C4 . H41 . 120.2 no
C4 . C5 . C6 . 119.79(16) yes
C4 . C5 . H51 . 120.8 no
C6 . C5 . H51 . 119.4 no
C5 . C6 . C7 . 120.58(16) yes
C5 . C6 . C8 . 119.87(16) yes
C7 . C6 . C8 . 119.52(16) yes
C6 . C7 . C2 . 118.24(15) yes
C6 . C7 . N11 . 117.61(15) yes
C2 . C7 . N11 . 124.14(15) yes
C6 . C8 . C9 . 120.20(16) yes
C6 . C8 . H81 . 119.1 no
C9 . C8 . H81 . 120.7 no
C8 . C9 . C10 . 119.06(17) yes
C8 . C9 . H91 . 121.8 no
C10 . C9 . H91 . 119.1 no
C9 . C10 . N11 . 122.71(17) yes
C9 . C10 . H101 . 120.9 no
N11 . C10 . H101 . 116.4 no
C7 . N11 . C10 . 120.81(14) yes
C7 . N11 . C12 . 124.03(14) yes
C10 . N11 . C12 . 115.12(14) yes
N11 . C12 . C13 . 111.55(13) yes
N11 . C12 . H121 . 110.3 no
C13 . C12 . H121 . 110.4 no
N11 . C12 . H122 . 106.7 no
C13 . C12 . H122 . 108.5 no
H121 . C12 . H122 . 109.2 no
C12 . C13 . C15 2_576 120.19(15) yes
C12 . C13 . C14 . 120.51(15) yes
C15 2_576 C13 . C14 . 119.27(15) yes
C13 . C14 . C15 . 120.00(16) yes
C13 . C14 . H141 . 119.0 no
C15 . C14 . H141 . 121.0 no
C13 2_576 C15 . C14 . 120.73(16) yes
C13 2_576 C15 . H151 . 120.0 no
C14 . C15 . H151 . 119.2 no

# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
####################################################################### 
# 
# 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_3_H
_database_code_depnum_ccdc_archive 'CCDC 2050546'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;
#==============================================================================
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.250 0.125 348 70 ' '
2 0.000 0.750 -0.125 348 70 ' '
3 0.500 0.250 0.375 348 70 ' '
4 0.500 0.750 -0.375 348 70 ' '
_platon_squeeze_details          
;
;

_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 asymmetric unit cell contains the monodeprotonated bis-quinolinium species
(i.e. the 1+ species containing one phenolate and one phenol oxygen atom),
and one PF6 anion. An area of diffuse electron density, which appeared
to correspond to disordered solvent located about a symmetry site was 
identified. This could not be modelled sensibly, and so PLATON-SQUEEZE was used
to include this electron density in the refinement.

C-H hydrogen atoms were generally visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. O-H hydrogen 
atoms were visible in the Fourier difference map and were refined
with restraints on bond lengths and angles. 

Other than this, it was not necessary to use any crystallographic restraints.,SQUEEZE
;

_cell_length_a                   23.4250(3)
_cell_length_b                   23.4250(3)
_cell_length_c                   18.7771(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10303.6(3)

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'I 41/a '
_symmetry_space_group_name_Hall  '-I 4ad'

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
y+3/4,-x+3/4,z+3/4
-y+3/4,x+3/4,-z+3/4
y+5/4,-x+5/4,z+5/4
-y+5/4,x+5/4,-z+5/4
x+1/2,y,-z+1/2
-x+1/2,-y,z+1/2
x+1,y+1/2,-z+1
-x+1,-y+1/2,z+1
-y+3/4,x+1/4,z+1/4
y+3/4,-x+1/4,-z+1/4
-y+5/4,x+3/4,z+3/4
y+5/4,-x+3/4,-z+3/4

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'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
I -0.3257 6.8362 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            16

_chemical_formula_sum            'C26 H21 F6 N2 O2 P'
_chemical_formula_moiety         'C26 H21 N2 O2, F6 P'
_chemical_compound_source        synthesized
_chemical_formula_weight         538.42


_cell_measurement_reflns_used    11328
_cell_measurement_theta_min      4.78
_cell_measurement_theta_max      72.3
_cell_measurement_temperature    150

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.04
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_max          0.36

_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             4416
_exptl_absorpt_coefficient_mu    1.580

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_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            42214
_reflns_number_total             5094
_diffrn_reflns_av_R_equivalents  0.041

_diffrn_reflns_theta_min         3.774
_diffrn_reflns_theta_max         72.566
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        72.566
_diffrn_measured_fraction_theta_full 0.995

_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23
_reflns_limit_h_min              -19
_reflns_limit_h_max              20
_reflns_limit_k_min              0
_reflns_limit_k_max              28
_reflns_limit_l_min              0
_reflns_limit_l_max              23

_oxford_diffrn_Wilson_B_factor   3.77
_oxford_diffrn_Wilson_scale      2.50

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.26
_refine_diff_density_max         0.25

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         5067
_refine_ls_number_restraints     2
_refine_ls_number_parameters     337
_oxford_refine_ls_R_factor_ref   0.0402
_refine_ls_wR_factor_ref         0.0845
_refine_ls_goodness_of_fit_ref   0.9499
_refine_ls_shift/su_max          0.0016235
_refine_ls_shift/su_mean         0.0000965

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5067
_refine_ls_R_factor_all          0.0402
_refine_ls_wR_factor_all         0.0845

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4292
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_gt          0.0763

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    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: 
 586. 956. 581. 242. 54.2 
;

# 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
O1 O 0.64867(5) 0.55726(5) 0.34224(6) 0.0353 1.0000 Uani D . . . . .
C2 C 0.59666(7) 0.55710(7) 0.36867(9) 0.0331 1.0000 Uani . . . . . .
C3 C 0.54934(7) 0.54318(7) 0.32724(11) 0.0409 1.0000 Uani . . . . . .
C4 C 0.49421(8) 0.54140(9) 0.35445(13) 0.0515 1.0000 Uani . . . . . .
C5 C 0.48389(8) 0.55486(9) 0.42409(13) 0.0536 1.0000 Uani . . . . . .
C6 C 0.58666(7) 0.57008(7) 0.44218(9) 0.0333 1.0000 Uani . . . . . .
C7 C 0.52953(8) 0.56942(8) 0.46908(11) 0.0436 1.0000 Uani . . . . . .
C8 C 0.52037(9) 0.58185(9) 0.54170(12) 0.0564 1.0000 Uani . . . . . .
C9 C 0.56471(10) 0.59241(9) 0.58612(12) 0.0563 1.0000 Uani . . . . . .
C10 C 0.61984(9) 0.59205(8) 0.55859(10) 0.0443 1.0000 Uani . . . . . .
N11 N 0.63034(6) 0.58244(6) 0.49004(7) 0.0336 1.0000 Uani . . . . . .
C12 C 0.69125(7) 0.58715(7) 0.46743(8) 0.0316 1.0000 Uani . . . . . .
C13 C 0.70274(6) 0.64265(7) 0.42843(9) 0.0310 1.0000 Uani . . . . . .
C14 C 0.67627(8) 0.69268(7) 0.45147(10) 0.0407 1.0000 Uani . . . . . .
C15 C 0.68956(8) 0.74533(8) 0.42207(12) 0.0484 1.0000 Uani . . . . . .
C16 C 0.72959(8) 0.74872(7) 0.36834(12) 0.0468 1.0000 Uani . . . . . .
C17 C 0.75518(7) 0.69929(7) 0.34351(10) 0.0390 1.0000 Uani . . . . . .
C18 C 0.74232(6) 0.64600(6) 0.37248(9) 0.0308 1.0000 Uani . . . . . .
C19 C 0.76872(6) 0.59284(7) 0.34027(9) 0.0305 1.0000 Uani . . . . . .
N20 N 0.82815(5) 0.60397(5) 0.31450(7) 0.0301 1.0000 Uani . . . . . .
C21 C 0.83448(8) 0.60764(7) 0.24418(9) 0.0363 1.0000 Uani . . . . . .
C22 C 0.88646(8) 0.62195(8) 0.21287(9) 0.0408 1.0000 Uani . . . . . .
C23 C 0.93196(7) 0.63278(7) 0.25595(10) 0.0388 1.0000 Uani . . . . . .
C24 C 0.87368(6) 0.61307(6) 0.36099(8) 0.0294 1.0000 Uani . . . . . .
C25 C 0.92726(7) 0.62856(6) 0.33063(9) 0.0331 1.0000 Uani . . . . . .
C26 C 0.97437(7) 0.64027(7) 0.37493(10) 0.0393 1.0000 Uani . . . . . .
C27 C 0.96834(7) 0.63626(8) 0.44717(10) 0.0420 1.0000 Uani . . . . . .
C28 C 0.91663(7) 0.61975(7) 0.47742(9) 0.0370 1.0000 Uani . . . . . .
C29 C 0.86839(7) 0.60668(6) 0.43697(9) 0.0307 1.0000 Uani . . . . . .
O30 O 0.82071(5) 0.58883(5) 0.46571(6) 0.0353 1.0000 Uani D . . . . .
P101 P 0.686858(17) 0.418684(17) 0.51798(2) 0.0335 1.0000 Uani . . . . . .
F102 F 0.72288(5) 0.39331(5) 0.58316(6) 0.0520 1.0000 Uani . . . . . .
F103 F 0.63666(5) 0.37392(5) 0.53440(7) 0.0527 1.0000 Uani . . . . . .
F104 F 0.65720(5) 0.46338(5) 0.56998(6) 0.0531 1.0000 Uani . . . . . .
F105 F 0.73625(5) 0.46318(5) 0.50153(7) 0.0578 1.0000 Uani . . . . . .
F106 F 0.71579(5) 0.37357(5) 0.46606(6) 0.0574 1.0000 Uani . . . . . .
F107 F 0.64983(5) 0.44368(5) 0.45321(6) 0.0512 1.0000 Uani . . . . . .
H31 H 0.5555 0.5360 0.2787 0.0494 1.0000 Uiso R . . . . .
H41 H 0.4646 0.5320 0.3245 0.0622 1.0000 Uiso R . . . . .
H51 H 0.4467 0.5551 0.4419 0.0652 1.0000 Uiso R . . . . .
H81 H 0.4829 0.5815 0.5594 0.0676 1.0000 Uiso R . . . . .
H91 H 0.5587 0.6003 0.6346 0.0648 1.0000 Uiso R . . . . .
H101 H 0.6501 0.5994 0.5890 0.0557 1.0000 Uiso R . . . . .
H121 H 0.7157 0.5864 0.5089 0.0374 1.0000 Uiso R . . . . .
H122 H 0.7012 0.5558 0.4366 0.0373 1.0000 Uiso R . . . . .
H141 H 0.6489 0.6902 0.4879 0.0492 1.0000 Uiso R . . . . .
H151 H 0.6714 0.7785 0.4384 0.0592 1.0000 Uiso R . . . . .
H161 H 0.7393 0.7846 0.3488 0.0564 1.0000 Uiso R . . . . .
H171 H 0.7831 0.7020 0.3062 0.0462 1.0000 Uiso R . . . . .
H191 H 0.7692 0.5632 0.3757 0.0355 1.0000 Uiso R . . . . .
H192 H 0.7451 0.5818 0.2994 0.0354 1.0000 Uiso R . . . . .
H211 H 0.8020 0.6007 0.2140 0.0463 1.0000 Uiso R . . . . .
H221 H 0.8911 0.6262 0.1631 0.0481 1.0000 Uiso R . . . . .
H231 H 0.9660 0.6409 0.2370 0.0454 1.0000 Uiso R . . . . .
H261 H 1.0102 0.6489 0.3546 0.0466 1.0000 Uiso R . . . . .
H271 H 1.0006 0.6415 0.4755 0.0496 1.0000 Uiso R . . . . .
H281 H 0.9137 0.6191 0.5286 0.0430 1.0000 Uiso R . . . . .
H302 H 0.6542(9) 0.5640(9) 0.2788(7) 0.0548 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.162(3)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.316(2) yes
O1 . H302 . 1.207(13) no
C2 . C3 . 1.393(2) yes
C2 . C6 . 1.433(2) yes
C3 . C4 . 1.389(3) yes
C3 . H31 . 0.938 no
C4 . C5 . 1.367(3) yes
C4 . H41 . 0.920 no
C5 . C7 . 1.405(3) yes
C5 . H51 . 0.933 no
C6 . C7 . 1.430(2) yes
C6 . N11 . 1.392(2) yes
C7 . C8 . 1.411(3) yes
C8 . C9 . 1.355(3) yes
C8 . H81 . 0.939 no
C9 . C10 . 1.391(3) yes
C9 . H91 . 0.940 no
C10 . N11 . 1.329(2) yes
C10 . H101 . 0.927 no
N11 . C12 . 1.493(2) yes
C12 . C13 . 1.516(2) yes
C12 . H121 . 0.966 no
C12 . H122 . 0.964 no
C13 . C14 . 1.395(2) yes
C13 . C18 . 1.403(2) yes
C14 . C15 . 1.386(3) yes
C14 . H141 . 0.940 no
C15 . C16 . 1.380(3) yes
C15 . H151 . 0.937 no
C16 . C17 . 1.385(3) yes
C16 . H161 . 0.945 no
C17 . C18 . 1.395(2) yes
C17 . H171 . 0.961 no
C18 . C19 . 1.516(2) yes
C19 . N20 . 1.4965(19) yes
C19 . H191 . 0.962 no
C19 . H192 . 0.980 no
N20 . C21 . 1.331(2) yes
N20 . C24 . 1.395(2) yes
C21 . C22 . 1.393(2) yes
C21 . H211 . 0.963 no
C22 . C23 . 1.362(3) yes
C22 . H221 . 0.946 no
C23 . C25 . 1.410(2) yes
C23 . H231 . 0.892 no
C24 . C25 . 1.425(2) yes
C24 . C29 . 1.440(2) yes
C25 . C26 . 1.409(2) yes
C26 . C27 . 1.367(3) yes
C26 . H261 . 0.945 no
C27 . C28 . 1.393(2) yes
C27 . H271 . 0.932 no
C28 . C29 . 1.396(2) yes
C28 . H281 . 0.963 no
C29 . O30 . 1.3091(19) yes
O30 . H302 7_454 1.207(13) no
P101 . F102 . 1.6010(11) yes
P101 . F103 . 1.6055(11) yes
P101 . F104 . 1.5913(11) yes
P101 . F105 . 1.5876(11) yes
P101 . F106 . 1.5896(11) yes
P101 . F107 . 1.6043(11) yes

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 . O1 . H302 . 118.1(10) no
O1 . C2 . C3 . 121.80(16) yes
O1 . C2 . C6 . 120.95(14) yes
C3 . C2 . C6 . 117.24(16) yes
C2 . C3 . C4 . 122.77(19) yes
C2 . C3 . H31 . 117.6 no
C4 . C3 . H31 . 119.6 no
C3 . C4 . C5 . 120.62(18) yes
C3 . C4 . H41 . 118.9 no
C5 . C4 . H41 . 120.5 no
C4 . C5 . C7 . 119.79(17) yes
C4 . C5 . H51 . 120.7 no
C7 . C5 . H51 . 119.5 no
C2 . C6 . C7 . 119.40(16) yes
C2 . C6 . N11 . 123.09(14) yes
C7 . C6 . N11 . 117.50(16) yes
C6 . C7 . C5 . 120.15(18) yes
C6 . C7 . C8 . 118.78(18) yes
C5 . C7 . C8 . 121.04(18) yes
C7 . C8 . C9 . 121.07(18) yes
C7 . C8 . H81 . 118.9 no
C9 . C8 . H81 . 120.0 no
C8 . C9 . C10 . 118.80(19) yes
C8 . C9 . H91 . 121.2 no
C10 . C9 . H91 . 120.0 no
C9 . C10 . N11 . 122.17(19) yes
C9 . C10 . H101 . 118.7 no
N11 . C10 . H101 . 119.1 no
C6 . N11 . C10 . 121.62(15) yes
C6 . N11 . C12 . 122.29(13) yes
C10 . N11 . C12 . 116.08(15) yes
N11 . C12 . C13 . 111.74(12) yes
N11 . C12 . H121 . 109.6 no
C13 . C12 . H121 . 107.5 no
N11 . C12 . H122 . 110.3 no
C13 . C12 . H122 . 108.7 no
H121 . C12 . H122 . 108.9 no
C12 . C13 . C14 . 119.47(15) yes
C12 . C13 . C18 . 121.78(14) yes
C14 . C13 . C18 . 118.62(15) yes
C13 . C14 . C15 . 121.62(17) yes
C13 . C14 . H141 . 118.4 no
C15 . C14 . H141 . 119.9 no
C14 . C15 . C16 . 119.67(17) yes
C14 . C15 . H151 . 120.3 no
C16 . C15 . H151 . 120.0 no
C15 . C16 . C17 . 119.48(17) yes
C15 . C16 . H161 . 119.9 no
C17 . C16 . H161 . 120.6 no
C16 . C17 . C18 . 121.58(17) yes
C16 . C17 . H171 . 119.0 no
C18 . C17 . H171 . 119.5 no
C13 . C18 . C17 . 119.00(15) yes
C13 . C18 . C19 . 121.48(14) yes
C17 . C18 . C19 . 119.43(15) yes
C18 . C19 . N20 . 111.42(12) yes
C18 . C19 . H191 . 108.8 no
N20 . C19 . H191 . 109.8 no
C18 . C19 . H192 . 107.4 no
N20 . C19 . H192 . 108.5 no
H191 . C19 . H192 . 110.9 no
C19 . N20 . C21 . 115.82(13) yes
C19 . N20 . C24 . 122.38(13) yes
C21 . N20 . C24 . 121.71(14) yes
N20 . C21 . C22 . 122.10(16) yes
N20 . C21 . H211 . 118.9 no
C22 . C21 . H211 . 119.0 no
C21 . C22 . C23 . 118.56(16) yes
C21 . C22 . H221 . 122.9 no
C23 . C22 . H221 . 118.4 no
C22 . C23 . C25 . 121.10(16) yes
C22 . C23 . H231 . 120.1 no
C25 . C23 . H231 . 118.7 no
N20 . C24 . C25 . 117.51(14) yes
N20 . C24 . C29 . 122.58(14) yes
C25 . C24 . C29 . 119.91(14) yes
C24 . C25 . C23 . 118.97(15) yes
C24 . C25 . C26 . 120.21(15) yes
C23 . C25 . C26 . 120.82(16) yes
C25 . C26 . C27 . 119.44(16) yes
C25 . C26 . H261 . 120.0 no
C27 . C26 . H261 . 120.5 no
C26 . C27 . C28 . 120.91(16) yes
C26 . C27 . H271 . 118.3 no
C28 . C27 . H271 . 120.5 no
C27 . C28 . C29 . 122.90(16) yes
C27 . C28 . H281 . 118.2 no
C29 . C28 . H281 . 118.9 no
C24 . C29 . C28 . 116.54(15) yes
C24 . C29 . O30 . 121.01(14) yes
C28 . C29 . O30 . 122.44(15) yes
H302 7_454 O30 . C29 . 118.2(10) no
F102 . P101 . F103 . 89.82(6) yes
F102 . P101 . F104 . 90.31(6) yes
F103 . P101 . F104 . 89.55(6) yes
F102 . P101 . F105 . 90.47(7) yes
F103 . P101 . F105 . 179.68(6) yes
F104 . P101 . F105 . 90.32(7) yes
F102 . P101 . F106 . 89.84(6) yes
F103 . P101 . F106 . 89.77(7) yes
F104 . P101 . F106 . 179.29(7) yes
F105 . P101 . F106 . 90.36(7) yes
F102 . P101 . F107 . 179.07(7) yes
F103 . P101 . F107 . 89.31(6) yes
F104 . P101 . F107 . 89.37(6) yes
F105 . P101 . F107 . 90.40(6) yes
F106 . P101 . F107 . 90.47(6) yes
O30 15_544 H302 . O1 . 178(2) 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
C19 . H192 . O30 15_544 162.04(4) 0.980 2.531 3.477(3) yes

_iucr_refine_instructions_details_constraints 
;
#
# Punched on 26/04/16 at 11:22:29
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT O    (    1 ,X'S,U'S)  UNTIL F    (  107 ) 
CONT H    (  302 ,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
END       
;

_iucr_refine_instructions_details_restraints 
;                                                                     
#
# Punched on 26/04/16 at 11:22:29
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 1) TO H(302) 
REST 0.054, 0.002 = H(302,U[ISO]) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 30) TO H(302,2,2,-1,0,-1) 
REST 0.054, 0.002 = H(302,2,2,-1,0,-1,U[ISO]) 
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
-4 6 0 x .
2 6 0 x .
4 4 0 x .
-2 6 0 x .
0 6 0 x .
4 6 0 x .
0 8 0 x .
####################################################################### 
# 
# 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_3SO4
_database_code_depnum_ccdc_archive 'CCDC 2050549'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;
#==============================================================================
# start Validation Reply Form
_vrf_PLAT029_3SO4                
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.920 Why?  
RESPONSE: Low data completion ratio is due to the limitations of the instrument
available at the Australian Synchrotron operating under rotation data 
collection with a fixed detector and affects some high angle data.
;

_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          
; 
C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. O-H hydrogen
atoms were initially inserted at idealised hydrogen bonding and then refined 
with restraints on bond lengths and angles.

Apart from the restraints on hydrogen atoms, it was not necessary to use any
crystallographic restraints in the refinement.
;

_cell_length_a                   7.7620(16)
_cell_length_b                   8.7260(17)
_cell_length_c                   18.728(4)
_cell_angle_alpha                85.64(3)
_cell_angle_beta                 88.48(3)
_cell_angle_gamma                89.71(3)
_cell_volume                     1264.3(4)

_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'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

_chemical_formula_sum            'C28 H30 N2 O8 S'
_chemical_formula_moiety         'C26 H22 N2 O2, O4 S, 2(C H4 O)'
_chemical_compound_source        synthesized
_chemical_formula_weight         554.62

_cell_measurement_reflns_used    16278
_cell_measurement_theta_min      1.091
_cell_measurement_theta_max      26.371
_cell_measurement_temperature    100

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.01
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_max          0.10

_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             583.996
_exptl_absorpt_coefficient_mu    0.185

_exptl_absorpt_correction_type   None

_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_measurement_device_type  'Dectris Eiger 16M'
_diffrn_measurement_method       'Omega Scan'

_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_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      100
_diffrn_reflns_number            16278
_diffrn_reflns_av_unetI/netI     0.161
_reflns_number_total             4751
_diffrn_reflns_av_R_equivalents  0.172

_diffrn_reflns_theta_min         1.091
_diffrn_reflns_theta_max         26.371
_diffrn_measured_fraction_theta_max 0.919

_diffrn_reflns_theta_full        25.053
_diffrn_measured_fraction_theta_full 0.920

_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -10
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              23

_oxford_diffrn_Wilson_B_factor   3.10
_oxford_diffrn_Wilson_scale      2.32

_atom_sites_solution_primary     other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.76
_refine_diff_density_max         0.92

_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     8
_refine_ls_number_parameters     368
_refine_ls_number_reflns         4511
_oxford_refine_ls_R_factor_ref   0.1600
_refine_ls_R_factor_all          0.1600
_refine_ls_wR_factor_ref         0.2194
_refine_ls_wR_factor_all         0.2194
_refine_ls_goodness_of_fit_ref   0.9047
_refine_ls_shift/su_max          0.0002298
_refine_ls_shift/su_mean         0.0000201

# Computed with I/sigma = -10 
_oxford_reflns_number_all        4511
_oxford_refine_ls_R_factor_all   0.1600
_oxford_refine_ls_wR_factor_all  0.2194

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2630
_refine_ls_R_factor_gt           0.1255
_refine_ls_wR_factor_gt          0.2038


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     
;
 Method= 
 SQRT(W) = 1/(Data with the key SIGMA(/FO/) in list 6) 
;

# 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
O1 O 0.5225(5) 0.3134(4) 0.58792(16) 0.0386 1.0000 Uani D . . . . .
C2 C 0.5647(6) 0.1645(5) 0.6008(2) 0.0304 1.0000 Uani . . . . . .
C3 C 0.5166(7) 0.0822(6) 0.6644(2) 0.0397 1.0000 Uani . . . . . .
C4 C 0.5521(7) -0.0752(6) 0.6752(3) 0.0423 1.0000 Uani . . . . . .
C5 C 0.6364(7) -0.1562(5) 0.6253(2) 0.0377 1.0000 Uani . . . . . .
C6 C 0.6936(6) -0.0749(5) 0.5606(2) 0.0319 1.0000 Uani . . . . . .
C7 C 0.6586(6) 0.0851(5) 0.5476(2) 0.0314 1.0000 Uani . . . . . .
C8 C 0.7769(6) -0.1551(5) 0.5083(3) 0.0357 1.0000 Uani . . . . . .
C9 C 0.8314(7) -0.0790(5) 0.4437(2) 0.0369 1.0000 Uani . . . . . .
C10 C 0.7982(7) 0.0755(5) 0.4331(2) 0.0365 1.0000 Uani . . . . . .
N11 N 0.7196(5) 0.1555(4) 0.48150(19) 0.0325 1.0000 Uani . . . . . .
C12 C 0.7012(6) 0.3283(5) 0.4604(2) 0.0316 1.0000 Uani . . . . . .
C13 C 0.8553(6) 0.4150(5) 0.4817(2) 0.0314 1.0000 Uani . . . . . .
C14 C 0.9519(6) 0.5022(5) 0.4301(2) 0.0338 1.0000 Uani . . . . . .
C15 C 0.9079(7) 0.4150(5) 0.5536(2) 0.0343 1.0000 Uani . . . . . .
O21 O 0.5593(5) 0.2738(4) 0.91762(15) 0.0387 1.0000 Uani D . . . . .
C22 C 0.6394(6) 0.1393(5) 0.9336(2) 0.0326 1.0000 Uani . . . . . .
C23 C 0.6587(7) 0.0310(5) 0.8849(2) 0.0372 1.0000 Uani . . . . . .
C24 C 0.7255(8) -0.1158(6) 0.9032(3) 0.0470 1.0000 Uani . . . . . .
C25 C 0.7766(7) -0.1532(6) 0.9708(3) 0.0449 1.0000 Uani . . . . . .
C26 C 0.7621(7) -0.0497(5) 1.0234(2) 0.0384 1.0000 Uani . . . . . .
C27 C 0.6972(6) 0.1029(5) 1.0055(2) 0.0290 1.0000 Uani . . . . . .
C28 C 0.8027(7) -0.0904(5) 1.0964(3) 0.0389 1.0000 Uani . . . . . .
C29 C 0.7792(7) 0.0085(5) 1.1471(2) 0.0387 1.0000 Uani . . . . . .
C30 C 0.7256(6) 0.1558(5) 1.1272(2) 0.0341 1.0000 Uani . . . . . .
N31 N 0.6881(5) 0.2023(4) 1.05965(18) 0.0313 1.0000 Uani . . . . . .
C32 C 0.6654(7) 0.3733(5) 1.0452(2) 0.0351 1.0000 Uani . . . . . .
C33 C 0.8375(7) 0.4400(5) 1.0206(2) 0.0326 1.0000 Uani . . . . . .
C34 C 0.8884(7) 0.4562(5) 0.9483(2) 0.0351 1.0000 Uani . . . . . .
C35 C 0.9497(7) 0.4854(5) 1.0720(2) 0.0380 1.0000 Uani . . . . . .
O51 O 0.5067(6) 0.4945(4) 0.68308(17) 0.0569 1.0000 Uani . . . . . .
O52 O 0.2630(6) 0.4858(5) 0.7649(3) 0.0697 1.0000 Uani . . . . . .
O53 O 0.4968(6) 0.3183(4) 0.78806(16) 0.0501 1.0000 Uani . . . . . .
O54 O 0.5277(6) 0.5953(4) 0.79872(19) 0.0554 1.0000 Uani . . . . . .
O101 O 1.0839(6) 0.2330(5) 0.7181(2) 0.0571 1.0000 Uani D . . . . .
C102 C 0.9155(8) 0.2595(7) 0.7456(3) 0.0507 1.0000 Uani . . . . . .
O111 O 0.8706(6) 0.2439(5) 0.28298(19) 0.0535 1.0000 Uani D . . . . .
C112 C 1.0423(9) 0.2455(9) 0.2551(3) 0.0699 1.0000 Uani . . . . . .
S51 S 0.45061(18) 0.47598(14) 0.75881(6) 0.0376 1.0000 Uani . . . . . .
H32 H 0.4592 0.1338 0.7011 0.0483 1.0000 Uiso R . . . . .
H42 H 0.5156 -0.1283 0.7191 0.0529 1.0000 Uiso R . . . . .
H52 H 0.6578 -0.2633 0.6335 0.0506 1.0000 Uiso R . . . . .
H82 H 0.7969 -0.2623 0.5169 0.0453 1.0000 Uiso R . . . . .
H92 H 0.8890 -0.1333 0.4080 0.0474 1.0000 Uiso R . . . . .
H102 H 0.8351 0.1282 0.3891 0.0499 1.0000 Uiso R . . . . .
H123 H 0.6014 0.3666 0.4836 0.0389 1.0000 Uiso R . . . . .
H124 H 0.6896 0.3429 0.4100 0.0389 1.0000 Uiso R . . . . .
H142 H 0.9203 0.5023 0.3814 0.0404 1.0000 Uiso R . . . . .
H152 H 0.8459 0.3554 0.5902 0.0419 1.0000 Uiso R . . . . .
H232 H 0.6216 0.0544 0.8374 0.0477 1.0000 Uiso R . . . . .
H242 H 0.7380 -0.1872 0.8676 0.0577 1.0000 Uiso R . . . . .
H252 H 0.8224 -0.2529 0.9822 0.0565 1.0000 Uiso R . . . . .
H282 H 0.8445 -0.1911 1.1090 0.0477 1.0000 Uiso R . . . . .
H292 H 0.8015 -0.0216 1.1958 0.0477 1.0000 Uiso R . . . . .
H302 H 0.7149 0.2279 1.1626 0.0421 1.0000 Uiso R . . . . .
H323 H 0.6284 0.4166 1.0881 0.0391 1.0000 Uiso R . . . . .
H324 H 0.5819 0.3939 1.0095 0.0391 1.0000 Uiso R . . . . .
H342 H 0.8112 0.4279 0.9131 0.0435 1.0000 Uiso R . . . . .
H352 H 0.9152 0.4765 1.1212 0.0499 1.0000 Uiso R . . . . .
H1011 H 1.148(8) 0.304(6) 0.729(4) 0.088(2) 1.0000 Uiso D . . . . .
H1021 H 0.8411 0.1803 0.7331 0.0665 1.0000 Uiso R . . . . .
H1022 H 0.8749 0.3559 0.7257 0.0665 1.0000 Uiso R . . . . .
H1023 H 0.9177 0.2602 0.7962 0.0665 1.0000 Uiso R . . . . .
H11 H 0.484(8) 0.360(7) 0.621(2) 0.060(2) 1.0000 Uiso D . . . . .
H1111 H 0.812(9) 0.323(5) 0.276(4) 0.083(2) 1.0000 Uiso D . . . . .
H1121 H 1.0980 0.1517 0.2699 0.0882 1.0000 Uiso R . . . . .
H1122 H 1.1022 0.3289 0.2727 0.0882 1.0000 Uiso R . . . . .
H1123 H 1.0419 0.2576 0.2042 0.0882 1.0000 Uiso R . . . . .
H211 H 0.510(7) 0.270(7) 0.881(2) 0.059(2) 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.557(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
O1 . C2 . 1.343(6) yes
O1 . H11 . 0.822(19) no
C2 . C3 . 1.388(6) yes
C2 . C7 . 1.437(7) yes
C3 . C4 . 1.400(7) yes
C3 . H32 . 0.950 no
C4 . C5 . 1.365(8) yes
C4 . H42 . 0.950 no
C5 . C6 . 1.419(7) yes
C5 . H52 . 0.950 no
C6 . C7 . 1.425(6) yes
C6 . C8 . 1.392(7) yes
C7 . N11 . 1.411(6) yes
C8 . C9 . 1.391(7) yes
C8 . H82 . 0.950 no
C9 . C10 . 1.372(6) yes
C9 . H92 . 0.950 no
C10 . N11 . 1.320(6) yes
C10 . H102 . 0.950 no
N11 . C12 . 1.537(5) yes
C12 . C13 . 1.498(6) yes
C12 . H123 . 0.950 no
C12 . H124 . 0.950 no
C13 . C14 . 1.390(6) yes
C13 . C15 . 1.417(5) yes
C14 . C15 2_766 1.364(7) yes
C14 . H142 . 0.950 no
C15 . H152 . 0.950 no
O21 . C22 . 1.342(5) yes
O21 . H211 . 0.806(19) no
C22 . C23 . 1.367(6) yes
C22 . C27 . 1.442(6) yes
C23 . C24 . 1.400(7) yes
C23 . H232 . 0.950 no
C24 . C25 . 1.352(7) yes
C24 . H242 . 0.950 no
C25 . C26 . 1.388(8) yes
C25 . H252 . 0.950 no
C26 . C27 . 1.439(6) yes
C26 . C28 . 1.431(6) yes
C27 . N31 . 1.384(6) yes
C28 . C29 . 1.339(7) yes
C28 . H282 . 0.950 no
C29 . C30 . 1.376(6) yes
C29 . H292 . 0.950 no
C30 . N31 . 1.338(5) yes
C30 . H302 . 0.950 no
N31 . C32 . 1.507(6) yes
C32 . C33 . 1.506(7) yes
C32 . H323 . 0.950 no
C32 . H324 . 0.950 no
C33 . C34 . 1.397(7) yes
C33 . C35 . 1.396(6) yes
C34 . C35 2_767 1.391(7) yes
C34 . H342 . 0.950 no
C35 . H352 . 0.950 no
O51 . S51 . 1.470(4) yes
O52 . S51 . 1.461(5) yes
O53 . S51 . 1.488(4) yes
O54 . S51 . 1.466(4) yes
O101 . C102 . 1.416(7) yes
O101 . H1011 . 0.839(19) no
C102 . H1021 . 0.950 no
C102 . H1022 . 0.950 no
C102 . H1023 . 0.950 no
O111 . C112 . 1.419(8) yes
O111 . H1111 . 0.828(19) no
C112 . H1121 . 0.950 no
C112 . H1122 . 0.950 no
C112 . H1123 . 0.950 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . H11 . 118(5) no
O1 . C2 . C3 . 121.6(5) yes
O1 . C2 . C7 . 120.3(4) yes
C3 . C2 . C7 . 118.1(4) yes
C2 . C3 . C4 . 120.9(5) yes
C2 . C3 . H32 . 119.3 no
C4 . C3 . H32 . 119.8 no
C3 . C4 . C5 . 123.0(5) yes
C3 . C4 . H42 . 118.6 no
C5 . C4 . H42 . 118.4 no
C4 . C5 . C6 . 117.8(4) yes
C4 . C5 . H52 . 121.6 no
C6 . C5 . H52 . 120.6 no
C5 . C6 . C7 . 120.7(5) yes
C5 . C6 . C8 . 119.0(4) yes
C7 . C6 . C8 . 120.1(4) yes
C2 . C7 . C6 . 119.4(4) yes
C2 . C7 . N11 . 124.1(4) yes
C6 . C7 . N11 . 116.5(4) yes
C6 . C8 . C9 . 120.4(4) yes
C6 . C8 . H82 . 119.5 no
C9 . C8 . H82 . 120.1 no
C8 . C9 . C10 . 118.1(5) yes
C8 . C9 . H92 . 120.6 no
C10 . C9 . H92 . 121.3 no
C9 . C10 . N11 . 123.2(5) yes
C9 . C10 . H102 . 118.6 no
N11 . C10 . H102 . 118.2 no
C7 . N11 . C10 . 121.6(4) yes
C7 . N11 . C12 . 123.3(4) yes
C10 . N11 . C12 . 115.2(4) yes
N11 . C12 . C13 . 111.1(3) yes
N11 . C12 . H123 . 109.3 no
C13 . C12 . H123 . 108.9 no
N11 . C12 . H124 . 108.7 no
C13 . C12 . H124 . 109.3 no
H123 . C12 . H124 . 109.5 no
C12 . C13 . C14 . 119.9(3) yes
C12 . C13 . C15 . 122.9(4) yes
C14 . C13 . C15 . 117.2(4) yes
C13 . C14 . C15 2_766 122.5(4) yes
C13 . C14 . H142 . 118.7 no
C15 2_766 C14 . H142 . 118.8 no
C13 . C15 . C14 2_766 120.3(4) yes
C13 . C15 . H152 . 119.4 no
C14 2_766 C15 . H152 . 120.3 no
C22 . O21 . H211 . 109(4) no
O21 . C22 . C23 . 121.9(4) yes
O21 . C22 . C27 . 119.4(4) yes
C23 . C22 . C27 . 118.5(4) yes
C22 . C23 . C24 . 122.4(4) yes
C22 . C23 . H232 . 119.0 no
C24 . C23 . H232 . 118.6 no
C23 . C24 . C25 . 119.8(5) yes
C23 . C24 . H242 . 119.7 no
C25 . C24 . H242 . 120.4 no
C24 . C25 . C26 . 121.4(5) yes
C24 . C25 . H252 . 118.8 no
C26 . C25 . H252 . 119.8 no
C25 . C26 . C27 . 119.7(4) yes
C25 . C26 . C28 . 122.4(5) yes
C27 . C26 . C28 . 117.8(4) yes
C22 . C27 . C26 . 118.0(4) yes
C22 . C27 . N31 . 124.6(4) yes
C26 . C27 . N31 . 117.4(4) yes
C26 . C28 . C29 . 121.5(4) yes
C26 . C28 . H282 . 118.6 no
C29 . C28 . H282 . 119.9 no
C28 . C29 . C30 . 118.8(4) yes
C28 . C29 . H292 . 120.7 no
C30 . C29 . H292 . 120.5 no
C29 . C30 . N31 . 122.6(4) yes
C29 . C30 . H302 . 119.1 no
N31 . C30 . H302 . 118.3 no
C27 . N31 . C30 . 121.6(4) yes
C27 . N31 . C32 . 122.6(3) yes
C30 . N31 . C32 . 115.0(4) yes
N31 . C32 . C33 . 107.8(4) yes
N31 . C32 . H323 . 109.4 no
C33 . C32 . H323 . 109.5 no
N31 . C32 . H324 . 109.8 no
C33 . C32 . H324 . 110.7 no
H323 . C32 . H324 . 109.5 no
C32 . C33 . C34 . 122.1(4) yes
C32 . C33 . C35 . 118.6(4) yes
C34 . C33 . C35 . 119.3(5) yes
C33 . C34 . C35 2_767 120.3(4) yes
C33 . C34 . H342 . 119.5 no
C35 2_767 C34 . H342 . 120.2 no
C33 . C35 . C34 2_767 120.4(5) yes
C33 . C35 . H352 . 119.8 no
C34 2_767 C35 . H352 . 119.8 no
C102 . O101 . H1011 . 108(6) no
O101 . C102 . H1021 . 109.5 no
O101 . C102 . H1022 . 109.3 no
H1021 . C102 . H1022 . 109.5 no
O101 . C102 . H1023 . 109.6 no
H1021 . C102 . H1023 . 109.5 no
H1022 . C102 . H1023 . 109.5 no
C112 . O111 . H1111 . 118(6) no
O111 . C112 . H1121 . 109.6 no
O111 . C112 . H1122 . 109.0 no
H1121 . C112 . H1122 . 109.5 no
O111 . C112 . H1123 . 109.8 no
H1121 . C112 . H1123 . 109.5 no
H1122 . C112 . H1123 . 109.5 no
O53 . S51 . O51 . 108.6(2) yes
O53 . S51 . O54 . 112.4(2) yes
O51 . S51 . O54 . 110.2(2) yes
O53 . S51 . O52 . 105.9(3) yes
O51 . S51 . O52 . 110.0(3) yes
O54 . S51 . O52 . 109.6(3) yes

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
C3 . H32 . O53 . 144 0.95 2.40 3.215(7) yes
C5 . H52 . O51 1_545 140 0.95 2.52 3.308(7) yes
C9 . H92 . O101 2_756 153 0.95 2.58 3.454(7) yes
C10 . H102 . O111 . 169 0.95 2.17 3.111(7) yes
C12 . H123 . O1 . 126 0.95 2.05 2.724(7) yes
C15 . H152 . O1 . 123 0.95 2.54 3.160(7) yes
C29 . H292 . O101 2_757 145 0.95 2.53 3.354(7) yes
C30 . H302 . O54 2_667 134 0.95 2.55 3.283(7) yes
C30 . H302 . O111 1_556 131 0.95 2.60 3.300(7) yes
C32 . H323 . O54 2_667 152 0.95 2.41 3.279(7) yes
C32 . H324 . O21 . 125 0.95 2.09 2.752(7) yes
C34 . H342 . O21 . 134 0.95 2.37 3.106(7) yes
C35 . H352 . O52 2_667 159 0.95 2.55 3.458(7) yes
O101 . H1011 . O52 1_655 170(8) 0.839(19) 1.99(3) 2.820(7) yes
O1 . H11 . O51 . 151(7) 0.822(19) 1.72(4) 2.470(7) yes
O111 . H1111 . O52 2_666 160(8) 0.828(19) 1.88(3) 2.673(7) yes
O21 . H211 . O53 . 150(7) 0.806(19) 1.76(4) 2.488(7) yes

# looking for ARCHIVE-HKL.CIF 

####################################################################### 
# 
# 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_4Br
_database_code_depnum_ccdc_archive 'CCDC 2050547'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;

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

_refine_special_details          
; 
C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. 

Otherwise, it was not necessary to use any crystallographic restraints
in the final refinement.
;

_cell_length_a                   9.8904(2)
_cell_length_b                   7.3341(2)
_cell_length_c                   22.6009(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.141(3)
_cell_angle_gamma                90
_cell_volume                     1626.69(5)

_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'
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

_chemical_formula_sum            'C19 H17 Br1 N2 O1'
_chemical_formula_moiety         'C17 H14 N O, C2 H3 N, Br'
_chemical_compound_source        synthesized
_chemical_formula_weight         369.26

_cell_measurement_reflns_used    15860
_cell_measurement_theta_min      3.76
_cell_measurement_theta_max      29.7
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.27
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_max          0.41

_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             751.997
_exptl_absorpt_coefficient_mu    2.533

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2011)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_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            31725
_reflns_number_total             3332
_diffrn_reflns_av_R_equivalents  0.028

_diffrn_reflns_theta_min         3.319
_diffrn_reflns_theta_max         26.361
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        26.361
_diffrn_measured_fraction_theta_full 0.999

_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              28

_oxford_diffrn_Wilson_B_factor   1.93
_oxford_diffrn_Wilson_scale      0.07

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.24
_refine_diff_density_max         0.36

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         3321
_refine_ls_number_restraints     0
_refine_ls_number_parameters     208
_oxford_refine_ls_R_factor_ref   0.0247
_refine_ls_wR_factor_ref         0.0438
_refine_ls_goodness_of_fit_ref   0.9504
_refine_ls_shift/su_max          0.0036282
_refine_ls_shift/su_mean         0.0000626

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3321
_refine_ls_R_factor_all          0.0247
_refine_ls_wR_factor_all         0.0438

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3098
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_gt          0.0428

_chemical_absolute_configuration .

_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, 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: 
 790. 0.118E+04 690. 290. 29.6 
;

# 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 0.73536(13) 0.26057(18) 0.57365(5) 0.0176 1.0000 Uani . . . . . .
C2 C 0.84019(16) 0.3041(2) 0.54459(7) 0.0236 1.0000 Uani . . . . . .
C3 C 0.82301(18) 0.3412(3) 0.48371(7) 0.0275 1.0000 Uani . . . . . .
C4 C 0.69531(18) 0.3386(2) 0.45336(7) 0.0258 1.0000 Uani . . . . . .
C5 C 0.58319(17) 0.2889(2) 0.48252(7) 0.0207 1.0000 Uani . . . . . .
C6 C 0.60424(15) 0.2446(2) 0.54404(7) 0.0173 1.0000 Uani . . . . . .
C7 C 0.44991(18) 0.2809(2) 0.45144(7) 0.0256 1.0000 Uani . . . . . .
C8 C 0.34285(18) 0.2322(2) 0.47993(8) 0.0284 1.0000 Uani . . . . . .
C9 C 0.36382(17) 0.1847(2) 0.54057(8) 0.0251 1.0000 Uani . . . . . .
C10 C 0.49158(16) 0.1860(2) 0.57233(7) 0.0192 1.0000 Uani . . . . . .
O11 O 0.51135(11) 0.11305(15) 0.62864(5) 0.0206 1.0000 Uani . . . . . .
C12 C 0.47857(16) 0.2320(2) 0.67578(7) 0.0219 1.0000 Uani . . . . . .
C13 C 0.56285(15) 0.4031(2) 0.68168(6) 0.0170 1.0000 Uani . . . . . .
C14 C 0.50632(16) 0.5569(2) 0.70538(7) 0.0206 1.0000 Uani . . . . . .
C15 C 0.58061(17) 0.7171(2) 0.71519(7) 0.0227 1.0000 Uani . . . . . .
C16 C 0.71236(16) 0.7261(2) 0.70001(7) 0.0213 1.0000 Uani . . . . . .
C17 C 0.76895(15) 0.5746(2) 0.67572(6) 0.0190 1.0000 Uani . . . . . .
C18 C 0.69594(14) 0.4129(2) 0.66694(6) 0.0160 1.0000 Uani . . . . . .
C19 C 0.76420(15) 0.2530(2) 0.64058(6) 0.0179 1.0000 Uani . . . . . .
N101 N -0.03624(19) -0.0793(3) 0.60166(10) 0.0518 1.0000 Uani . . . . . .
C102 C 0.06261(19) -0.0807(3) 0.63284(9) 0.0326 1.0000 Uani . . . . . .
C103 C 0.18950(18) -0.0824(3) 0.67283(8) 0.0319 1.0000 Uani . . . . . .
Br1 Br 0.126901(15) 0.42285(2) 0.660257(8) 0.0253 1.0000 Uani . . . . . .
H21 H 0.9259 0.3136 0.5681 0.0287 1.0000 Uiso R . . . . .
H31 H 0.9023 0.3707 0.4645 0.0335 1.0000 Uiso R . . . . .
H41 H 0.6802 0.3694 0.4115 0.0308 1.0000 Uiso R . . . . .
H71 H 0.4396 0.3088 0.4127 0.0309 1.0000 Uiso R . . . . .
H81 H 0.2554 0.2248 0.4595 0.0352 1.0000 Uiso R . . . . .
H91 H 0.2920 0.1471 0.5616 0.0314 1.0000 Uiso R . . . . .
H121 H 0.4927 0.1589 0.7116 0.0268 1.0000 Uiso R . . . . .
H122 H 0.3777 0.2648 0.6701 0.0275 1.0000 Uiso R . . . . .
H141 H 0.4091 0.5522 0.7134 0.0245 1.0000 Uiso R . . . . .
H151 H 0.5384 0.8185 0.7318 0.0280 1.0000 Uiso R . . . . .
H161 H 0.7647 0.8370 0.7053 0.0261 1.0000 Uiso R . . . . .
H171 H 0.8607 0.5805 0.6656 0.0234 1.0000 Uiso R . . . . .
H191 H 0.8613 0.2620 0.6495 0.0238 1.0000 Uiso R . . . . .
H192 H 0.7325 0.1345 0.6541 0.0222 1.0000 Uiso R . . . . .
H1031 H 0.2021 0.0292 0.6931 0.0503 1.0000 Uiso R . . . . .
H1032 H 0.1978 -0.1828 0.7013 0.0520 1.0000 Uiso R . . . . .
H1033 H 0.2692 -0.0974 0.6491 0.0498 1.0000 Uiso R . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.38(3)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.333(2) yes
N1 . C6 . 1.3883(19) yes
N1 . C19 . 1.5053(18) yes
C2 . C3 . 1.392(2) yes
C2 . H21 . 0.945 no
C3 . C4 . 1.360(2) yes
C3 . H31 . 0.967 no
C4 . C5 . 1.407(2) yes
C4 . H41 . 0.965 no
C5 . C6 . 1.418(2) yes
C5 . C7 . 1.416(2) yes
C6 . C10 . 1.418(2) yes
C7 . C8 . 1.354(3) yes
C7 . H71 . 0.892 no
C8 . C9 . 1.404(2) yes
C8 . H81 . 0.930 no
C9 . C10 . 1.374(2) yes
C9 . H91 . 0.943 no
C10 . O11 . 1.3719(18) yes
O11 . C12 . 1.4448(19) yes
C12 . C13 . 1.503(2) yes
C12 . H121 . 0.966 no
C12 . H122 . 1.018 no
C13 . C14 . 1.396(2) yes
C13 . C18 . 1.399(2) yes
C14 . C15 . 1.389(2) yes
C14 . H141 . 1.001 no
C15 . C16 . 1.390(2) yes
C15 . H151 . 0.953 no
C16 . C17 . 1.387(2) yes
C16 . H161 . 0.964 no
C17 . C18 . 1.390(2) yes
C17 . H171 . 0.965 no
C18 . C19 . 1.512(2) yes
C19 . H191 . 0.959 no
C19 . H192 . 0.985 no
N101 . C102 . 1.132(3) yes
C102 . C103 . 1.453(3) yes
C103 . H1031 . 0.938 no
C103 . H1032 . 0.975 no
C103 . H1033 . 1.013 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 . 121.33(13) yes
C2 . N1 . C19 . 116.24(13) yes
C6 . N1 . C19 . 122.02(12) yes
N1 . C2 . C3 . 121.79(15) yes
N1 . C2 . H21 . 116.0 no
C3 . C2 . H21 . 122.2 no
C2 . C3 . C4 . 119.16(16) yes
C2 . C3 . H31 . 118.8 no
C4 . C3 . H31 . 122.0 no
C3 . C4 . C5 . 120.26(15) yes
C3 . C4 . H41 . 120.8 no
C5 . C4 . H41 . 119.0 no
C4 . C5 . C6 . 119.38(15) yes
C4 . C5 . C7 . 121.19(15) yes
C6 . C5 . C7 . 119.42(15) yes
C5 . C6 . N1 . 117.89(14) yes
C5 . C6 . C10 . 118.92(14) yes
N1 . C6 . C10 . 123.19(14) yes
C5 . C7 . C8 . 120.67(15) yes
C5 . C7 . H71 . 117.6 no
C8 . C7 . H71 . 121.8 no
C7 . C8 . C9 . 120.01(15) yes
C7 . C8 . H81 . 120.9 no
C9 . C8 . H81 . 119.1 no
C8 . C9 . C10 . 121.54(16) yes
C8 . C9 . H91 . 122.3 no
C10 . C9 . H91 . 116.1 no
C6 . C10 . C9 . 119.32(15) yes
C6 . C10 . O11 . 120.45(13) yes
C9 . C10 . O11 . 119.87(15) yes
C10 . O11 . C12 . 115.42(12) yes
O11 . C12 . C13 . 113.37(12) yes
O11 . C12 . H121 . 105.1 no
C13 . C12 . H121 . 111.6 no
O11 . C12 . H122 . 110.9 no
C13 . C12 . H122 . 109.8 no
H121 . C12 . H122 . 105.9 no
C12 . C13 . C14 . 117.69(13) yes
C12 . C13 . C18 . 123.35(14) yes
C14 . C13 . C18 . 118.90(15) yes
C13 . C14 . C15 . 121.07(14) yes
C13 . C14 . H141 . 118.8 no
C15 . C14 . H141 . 120.1 no
C14 . C15 . C16 . 119.64(15) yes
C14 . C15 . H151 . 118.3 no
C16 . C15 . H151 . 122.0 no
C15 . C16 . C17 . 119.77(15) yes
C15 . C16 . H161 . 121.0 no
C17 . C16 . H161 . 119.2 no
C16 . C17 . C18 . 120.78(14) yes
C16 . C17 . H171 . 119.8 no
C18 . C17 . H171 . 119.4 no
C13 . C18 . C17 . 119.82(14) yes
C13 . C18 . C19 . 122.22(14) yes
C17 . C18 . C19 . 117.95(13) yes
C18 . C19 . N1 . 109.23(12) yes
C18 . C19 . H191 . 110.4 no
N1 . C19 . H191 . 105.6 no
C18 . C19 . H192 . 112.8 no
N1 . C19 . H192 . 108.4 no
H191 . C19 . H192 . 110.2 no
N101 . C102 . C103 . 179.9(2) yes
C102 . C103 . H1031 . 110.4 no
C102 . C103 . H1032 . 114.4 no
H1031 . C103 . H1032 . 110.0 no
C102 . C103 . H1033 . 109.9 no
H1031 . C103 . H1033 . 106.7 no
H1032 . C103 . H1033 . 105.1 no

_iucr_refine_instructions_details_constraints 
;
#
# Punched on 10/10/16 at 10:14:53
#
#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   (   4,X'S) H   (  41,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   ( 103,X'S) H   (1031,X'S) H   (1032,X'S) H   (1033,X'S) 
END
;

_iucr_refine_instructions_details_restraints 
;                                                                         
#
# Punched on 10/10/16 at 10:14:53
#
#LIST     16                                                                    
NO 
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
-1 2 2 x .
0 0 6 x .
####################################################################### 
# 
# 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_COMPOUNDNAME
_database_code_depnum_ccdc_archive 'CCDC 2050545'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
The asymmetric unit cell contains the bis-quinolinium dication, one PF6 anion,
one bromide anion and one acetonitrile solvate. The PF6 anion exhibits 
postitional disorder - this was modelled by having two positions for the four
equatorial fluorine atoms (s.o.fs: 0.75:0.25).

C-H hydrogen atoms were generally visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. O-H hydrogen 
atoms were visible in the Fourier difference map and were refined
with restraints on bond lengths and angles. 

Other than this, it was not necessary to use any crystallographic restraints
in the final refinement.
;

_cell_length_a                   14.3441(2)
_cell_length_b                   11.43670(10)
_cell_length_c                   16.6982(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.8455(11)
_cell_angle_gamma                90
_cell_volume                     2739.03(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,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 0.0181 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'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            4

_chemical_formula_sum            'C28 H25 Br1 F6 N3 O2 P1'
_chemical_formula_moiety         'C26 H22 N2 O2, F6 P, C2 H3 N, Br'
_chemical_compound_source        synthesized
_chemical_formula_weight         660.39

_cell_measurement_reflns_used    18974
_cell_measurement_theta_min      3
_cell_measurement_theta_max      72
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_max          0.27

_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1335.994
_exptl_absorpt_coefficient_mu    3.261

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_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            32508
_reflns_number_total             5413
_diffrn_reflns_av_R_equivalents  0.024

_diffrn_reflns_theta_min         4.687
_diffrn_reflns_theta_max         72.401
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        72.401
_diffrn_measured_fraction_theta_full 0.998

_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -17
_reflns_limit_h_max              17
_reflns_limit_k_min              0
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   2.86
_oxford_diffrn_Wilson_scale      0.19

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.55
_refine_diff_density_max         0.47

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         5391
_refine_ls_number_restraints     2
_refine_ls_number_parameters     412
_oxford_refine_ls_R_factor_ref   0.0357
_refine_ls_wR_factor_ref         0.0809
_refine_ls_goodness_of_fit_ref   0.9539
_refine_ls_shift/su_max          0.0008983
_refine_ls_shift/su_mean         0.0000336

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5391
_refine_ls_R_factor_all          0.0357
_refine_ls_wR_factor_all         0.0809

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5214
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_gt          0.0805

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    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: 
 0.113E+04 0.187E+04 0.114E+04 456. 91.0 
;

# 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
F102 F 0.48774(11) 0.69171(13) 0.43747(9) 0.0573 1.0000 Uani . . . . . .
F103 F 0.3914(2) 0.7882(4) 0.3531(3) 0.1065 0.7500 Uani . . . . 1 .
F104 F 0.4715(3) 0.8835(3) 0.44775(16) 0.0817 0.7500 Uani . . . . 1 .
F105 F 0.60244(17) 0.8067(3) 0.40159(19) 0.0832 0.7500 Uani . . . . 1 .
F106 F 0.5239(4) 0.7123(3) 0.30641(14) 0.0908 0.7500 Uani . . . . 1 .
F107 F 0.50069(14) 0.90382(15) 0.31361(10) 0.0782 1.0000 Uani . . . . . .
F113 F 0.4453(9) 0.7081(7) 0.3107(4) 0.0748 0.2500 Uani . . . . 2 .
F114 F 0.3877(7) 0.8314(13) 0.3964(6) 0.0998 0.2500 Uani . . . . 2 .
F115 F 0.5314(9) 0.8898(7) 0.4300(5) 0.0905 0.2500 Uani . . . . 2 .
F116 F 0.5892(6) 0.7593(9) 0.3491(8) 0.0915 0.2500 Uani . . . . 2 .
O1 O -0.01343(9) 0.52876(12) 0.37505(9) 0.0364 1.0000 Uani D . . . . .
C2 C -0.07411(12) 0.46531(16) 0.32976(11) 0.0303 1.0000 Uani . . . . . .
C3 C -0.14648(14) 0.51692(19) 0.28785(13) 0.0404 1.0000 Uani . . . . . .
C4 C -0.20914(14) 0.4520(2) 0.24057(13) 0.0475 1.0000 Uani . . . . . .
C5 C -0.19956(14) 0.3349(2) 0.23449(12) 0.0427 1.0000 Uani . . . . . .
C6 C -0.06358(11) 0.34178(16) 0.32582(10) 0.0250 1.0000 Uani . . . . . .
C7 C -0.12705(12) 0.27680(18) 0.27678(11) 0.0325 1.0000 Uani . . . . . .
C8 C -0.11800(13) 0.15506(19) 0.27139(12) 0.0383 1.0000 Uani . . . . . .
C9 C -0.05037(14) 0.09835(17) 0.31382(13) 0.0394 1.0000 Uani . . . . . .
C10 C 0.01039(13) 0.16318(17) 0.36171(12) 0.0334 1.0000 Uani . . . . . .
N11 N 0.00521(10) 0.27964(13) 0.36744(9) 0.0260 1.0000 Uani . . . . . .
C12 C 0.07662(11) 0.33522(16) 0.42064(10) 0.0270 1.0000 Uani . . . . . .
C13 C 0.15923(11) 0.38266(14) 0.37618(10) 0.0240 1.0000 Uani . . . . . .
C14 C 0.17519(12) 0.35778(15) 0.29653(10) 0.0270 1.0000 Uani . . . . . .
C15 C 0.25526(13) 0.39678(16) 0.25902(11) 0.0308 1.0000 Uani . . . . . .
C16 C 0.31966(12) 0.46321(18) 0.30166(11) 0.0335 1.0000 Uani . . . . . .
C17 C 0.30467(12) 0.48836(17) 0.38171(11) 0.0329 1.0000 Uani . . . . . .
C18 C 0.22575(11) 0.44806(15) 0.41968(10) 0.0265 1.0000 Uani . . . . . .
C19 C 0.20926(12) 0.46647(17) 0.50796(10) 0.0311 1.0000 Uani . . . . . .
N20 N 0.27912(10) 0.54353(15) 0.54837(9) 0.0345 1.0000 Uani . . . . . .
C21 C 0.34914(14) 0.4878(2) 0.58545(13) 0.0443 1.0000 Uani . . . . . .
C22 C 0.41563(15) 0.5459(3) 0.63178(14) 0.0517 1.0000 Uani . . . . . .
C23 C 0.40837(15) 0.6633(3) 0.64016(13) 0.0496 1.0000 Uani . . . . . .
C24 C 0.33746(14) 0.7270(2) 0.59944(12) 0.0407 1.0000 Uani . . . . . .
C25 C 0.27161(13) 0.66439(19) 0.55133(11) 0.0335 1.0000 Uani . . . . . .
C26 C 0.33180(17) 0.8487(2) 0.60676(13) 0.0500 1.0000 Uani . . . . . .
C27 C 0.26450(19) 0.9080(2) 0.56665(14) 0.0527 1.0000 Uani . . . . . .
C28 C 0.19958(17) 0.8493(2) 0.51776(13) 0.0444 1.0000 Uani . . . . . .
C29 C 0.20062(14) 0.72932(19) 0.50963(12) 0.0379 1.0000 Uani . . . . . .
O30 O 0.13894(12) 0.67200(15) 0.46265(10) 0.0504 1.0000 Uani D . . . . .
P101 P 0.49375(4) 0.79870(5) 0.37561(3) 0.0399 1.0000 Uani . . . . . .
N201 N 0.77473(15) 0.8810(2) 0.56385(15) 0.0603 1.0000 Uani . . . . . .
C202 C 0.69932(16) 0.8632(2) 0.58126(14) 0.0446 1.0000 Uani . . . . . .
C203 C 0.60575(18) 0.8416(3) 0.60559(17) 0.0601 1.0000 Uani . . . . . .
Br1 Br -0.037989(15) 0.800426(17) 0.389503(12) 0.0378 1.0000 Uani . . . . . .
H31 H -0.1538 0.5990 0.2908 0.0507 1.0000 Uiso R . . . . .
H41 H -0.2597 0.4924 0.2141 0.0575 1.0000 Uiso R . . . . .
H51 H -0.2397 0.2914 0.2019 0.0533 1.0000 Uiso R . . . . .
H81 H -0.1597 0.1135 0.2393 0.0471 1.0000 Uiso R . . . . .
H91 H -0.0445 0.0164 0.3113 0.0481 1.0000 Uiso R . . . . .
H101 H 0.0602 0.1248 0.3904 0.0401 1.0000 Uiso R . . . . .
H121 H 0.0470 0.3968 0.4505 0.0332 1.0000 Uiso R . . . . .
H122 H 0.0984 0.2758 0.4578 0.0333 1.0000 Uiso R . . . . .
H141 H 0.1315 0.3159 0.2663 0.0331 1.0000 Uiso R . . . . .
H151 H 0.2652 0.3787 0.2045 0.0376 1.0000 Uiso R . . . . .
H161 H 0.3737 0.4898 0.2750 0.0425 1.0000 Uiso R . . . . .
H171 H 0.3477 0.5344 0.4099 0.0410 1.0000 Uiso R . . . . .
H191 H 0.1486 0.5019 0.5147 0.0389 1.0000 Uiso R . . . . .
H192 H 0.2130 0.3899 0.5354 0.0396 1.0000 Uiso R . . . . .
H211 H 0.3514 0.4061 0.5779 0.0554 1.0000 Uiso R . . . . .
H221 H 0.4633 0.5027 0.6553 0.0625 1.0000 Uiso R . . . . .
H231 H 0.4499 0.7025 0.6739 0.0592 1.0000 Uiso R . . . . .
H261 H 0.3763 0.8902 0.6390 0.0616 1.0000 Uiso R . . . . .
H271 H 0.2604 0.9904 0.5712 0.0657 1.0000 Uiso R . . . . .
H281 H 0.1524 0.8921 0.4914 0.0527 1.0000 Uiso R . . . . .
H2031 H 0.5809 0.7762 0.5778 0.0912 1.0000 Uiso R . . . . .
H2033 H 0.6052 0.8277 0.6609 0.0921 1.0000 Uiso R . . . . .
H2032 H 0.5676 0.9073 0.5925 0.0922 1.0000 Uiso R . . . . .
H11 H -0.0241(19) 0.5985(15) 0.3730(17) 0.0550 1.0000 Uiso D . . . . .
H301 H 0.101(2) 0.719(2) 0.4444(19) 0.0761 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.431(12)

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
F102 . P101 . 1.6044(14) yes
F103 . P101 . 1.515(3) yes
F104 . P101 . 1.583(3) yes
F105 . P101 . 1.615(2) yes
F106 . P101 . 1.585(2) yes
F107 . P101 . 1.5906(16) yes
F113 . P101 . 1.645(6) yes
F114 . P101 . 1.610(9) yes
F115 . P101 . 1.479(7) yes
F116 . P101 . 1.514(6) yes
O1 . C2 . 1.355(2) yes
O1 . H11 . 0.813(17) no
C2 . C3 . 1.376(3) yes
C2 . C6 . 1.422(3) yes
C3 . C4 . 1.400(3) yes
C3 . H31 . 0.945 no
C4 . C5 . 1.351(4) yes
C4 . H41 . 0.962 no
C5 . C7 . 1.414(3) yes
C5 . H51 . 0.930 no
C6 . C7 . 1.425(2) yes
C6 . N11 . 1.393(2) yes
C7 . C8 . 1.401(3) yes
C8 . C9 . 1.358(3) yes
C8 . H81 . 0.928 no
C9 . C10 . 1.389(3) yes
C9 . H91 . 0.942 no
C10 . N11 . 1.337(2) yes
C10 . H101 . 0.960 no
N11 . C12 . 1.489(2) yes
C12 . C13 . 1.508(2) yes
C12 . H121 . 0.965 no
C12 . H122 . 0.969 no
C13 . C14 . 1.383(2) yes
C13 . C18 . 1.406(2) yes
C14 . C15 . 1.390(2) yes
C14 . H141 . 0.931 no
C15 . C16 . 1.385(3) yes
C15 . H151 . 0.947 no
C16 . C17 . 1.387(3) yes
C16 . H161 . 0.950 no
C17 . C18 . 1.385(2) yes
C17 . H171 . 0.933 no
C18 . C19 . 1.511(2) yes
C19 . N20 . 1.489(2) yes
C19 . H191 . 0.968 no
C19 . H192 . 0.989 no
N20 . C21 . 1.334(3) yes
N20 . C25 . 1.387(3) yes
C21 . C22 . 1.389(3) yes
C21 . H211 . 0.943 no
C22 . C23 . 1.353(4) yes
C22 . H221 . 0.927 no
C23 . C24 . 1.417(3) yes
C23 . H231 . 0.928 no
C24 . C25 . 1.424(3) yes
C24 . C26 . 1.400(4) yes
C25 . C29 . 1.433(3) yes
C26 . C27 . 1.349(4) yes
C26 . H261 . 0.956 no
C27 . C28 . 1.401(3) yes
C27 . H271 . 0.947 no
C28 . C29 . 1.379(3) yes
C28 . H281 . 0.940 no
C29 . O30 . 1.345(3) yes
O30 . H301 . 0.820(17) no
N201 . C202 . 1.142(3) yes
C202 . C203 . 1.430(3) yes
C203 . H2031 . 0.947 no
C203 . H2033 . 0.937 no
C203 . H2032 . 0.953 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 . O1 . H11 . 112.5(19) no
O1 . C2 . C3 . 121.83(18) yes
O1 . C2 . C6 . 119.33(15) yes
C3 . C2 . C6 . 118.83(18) yes
C2 . C3 . C4 . 122.2(2) yes
C2 . C3 . H31 . 118.8 no
C4 . C3 . H31 . 119.0 no
C3 . C4 . C5 . 120.19(19) yes
C3 . C4 . H41 . 118.6 no
C5 . C4 . H41 . 121.2 no
C4 . C5 . C7 . 120.21(19) yes
C4 . C5 . H51 . 120.7 no
C7 . C5 . H51 . 119.0 no
C2 . C6 . C7 . 118.51(16) yes
C2 . C6 . N11 . 123.95(15) yes
C7 . C6 . N11 . 117.54(16) yes
C6 . C7 . C5 . 120.07(19) yes
C6 . C7 . C8 . 119.75(17) yes
C5 . C7 . C8 . 120.18(18) yes
C7 . C8 . C9 . 120.48(18) yes
C7 . C8 . H81 . 119.1 no
C9 . C8 . H81 . 120.4 no
C8 . C9 . C10 . 118.89(19) yes
C8 . C9 . H91 . 121.1 no
C10 . C9 . H91 . 120.0 no
C9 . C10 . N11 . 122.53(18) yes
C9 . C10 . H101 . 119.9 no
N11 . C10 . H101 . 117.5 no
C6 . N11 . C10 . 120.80(15) yes
C6 . N11 . C12 . 123.77(14) yes
C10 . N11 . C12 . 115.44(15) yes
N11 . C12 . C13 . 113.49(14) yes
N11 . C12 . H121 . 108.4 no
C13 . C12 . H121 . 110.3 no
N11 . C12 . H122 . 107.1 no
C13 . C12 . H122 . 108.6 no
H121 . C12 . H122 . 108.8 no
C12 . C13 . C14 . 122.81(15) yes
C12 . C13 . C18 . 117.98(15) yes
C14 . C13 . C18 . 119.06(15) yes
C13 . C14 . C15 . 121.14(16) yes
C13 . C14 . H141 . 120.4 no
C15 . C14 . H141 . 118.4 no
C14 . C15 . C16 . 119.59(16) yes
C14 . C15 . H151 . 120.0 no
C16 . C15 . H151 . 120.4 no
C15 . C16 . C17 . 119.83(16) yes
C15 . C16 . H161 . 118.6 no
C17 . C16 . H161 . 121.6 no
C16 . C17 . C18 . 120.78(16) yes
C16 . C17 . H171 . 119.5 no
C18 . C17 . H171 . 119.7 no
C13 . C18 . C17 . 119.59(16) yes
C13 . C18 . C19 . 117.60(15) yes
C17 . C18 . C19 . 122.76(15) yes
C18 . C19 . N20 . 114.24(15) yes
C18 . C19 . H191 . 109.0 no
N20 . C19 . H191 . 107.5 no
C18 . C19 . H192 . 108.6 no
N20 . C19 . H192 . 106.4 no
H191 . C19 . H192 . 111.1 no
C19 . N20 . C21 . 115.13(18) yes
C19 . N20 . C25 . 123.63(15) yes
C21 . N20 . C25 . 121.17(17) yes
N20 . C21 . C22 . 122.4(2) yes
N20 . C21 . H211 . 116.0 no
C22 . C21 . H211 . 121.6 no
C21 . C22 . C23 . 118.6(2) yes
C21 . C22 . H221 . 118.5 no
C23 . C22 . H221 . 122.9 no
C22 . C23 . C24 . 121.1(2) yes
C22 . C23 . H231 . 119.5 no
C24 . C23 . H231 . 119.4 no
C23 . C24 . C25 . 118.5(2) yes
C23 . C24 . C26 . 120.8(2) yes
C25 . C24 . C26 . 120.7(2) yes
C24 . C25 . N20 . 118.03(19) yes
C24 . C25 . C29 . 118.3(2) yes
N20 . C25 . C29 . 123.65(17) yes
C24 . C26 . C27 . 119.9(2) yes
C24 . C26 . H261 . 120.2 no
C27 . C26 . H261 . 119.9 no
C26 . C27 . C28 . 120.9(2) yes
C26 . C27 . H271 . 120.3 no
C28 . C27 . H271 . 118.8 no
C27 . C28 . C29 . 121.7(2) yes
C27 . C28 . H281 . 119.5 no
C29 . C28 . H281 . 118.7 no
C25 . C29 . C28 . 118.47(19) yes
C25 . C29 . O30 . 119.19(19) yes
C28 . C29 . O30 . 122.3(2) yes
C29 . O30 . H301 . 109(2) no
F105 . P101 . F102 . 86.05(12) yes
F105 . P101 . F107 . 93.59(14) yes
F102 . P101 . F107 . 179.24(10) yes
F105 . P101 . F106 . 87.6(2) yes
F102 . P101 . F106 . 90.68(13) yes
F107 . P101 . F106 . 88.65(13) yes
F105 . P101 . F104 . 88.03(18) yes
F102 . P101 . F104 . 87.93(13) yes
F107 . P101 . F104 . 92.72(13) yes
F106 . P101 . F104 . 175.5(2) yes
F105 . P101 . F103 . 178.23(18) yes
F102 . P101 . F103 . 92.19(15) yes
F107 . P101 . F103 . 88.18(16) yes
F106 . P101 . F103 . 92.5(2) yes
F104 . P101 . F103 . 91.8(2) yes
N201 . C202 . C203 . 178.2(3) yes
C202 . C203 . H2031 . 110.2 no
C202 . C203 . H2033 . 109.3 no
H2031 . C203 . H2033 . 109.9 no
C202 . C203 . H2032 . 109.6 no
H2031 . C203 . H2032 . 107.5 no
H2033 . C203 . H2032 . 110.4 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C10 . H101 . N201 2_666 150.05(7) 0.960 2.478 3.345(3) yes
C12 . H122 . N201 2_666 128.22(6) 0.969 2.584 3.273(3) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 26/04/16 at 16: 6:39
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT F    (  102 ,X'S,U'S)  UNTIL BR   (    1 ) 
CONT H    (   11 ,X'S)  UNTIL H    (  301 ) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   ( 203,X'S) H   (2031,X'S) H   (2033,X'S) H   (2032,X'S) 
END     
;

_iucr_refine_instructions_details_restraints 
;                                                                        
#
# Punched on 26/04/16 at 16: 6:39
#
#LIST     16                                                                    
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 1) TO H(11) 
REST 0.055, 0.002 = H(11,U[ISO]) 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 30) TO H(301) 
REST 0.076, 0.002 = H(301,U[ISO]) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# 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_DBUHPF6
_database_code_depnum_ccdc_archive 'CCDC 2050548'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-03-08 downloaded from the CCDC.
;
#==============================================================================
# start Validation Reply Form
_vrf_PLAT029_DBUHPF6             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.947 Why?  
RESPONSE: Low data completion ratio is due to the limitations of the instrument 
available at the Australian Synchrotron operating under rotation data collection with a
fixed detector and affects some high angle data.
;

_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          
; 
Hydrogen atoms were visible in the Fourier difference map. The N-H protons 
were refined with restraints on bond lengths and angles. The  C-H
protons were initially refined with restraints on bond lengths and angles, 
after which the positions were used as the basis for a riding model. 

Apart from restraints on N-H bond lengths and angles, it was not necessary
to use any crystallographic restraints.
;

_cell_length_a                   6.294(3)
_cell_length_b                   26.438(2)
_cell_length_c                   7.670(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.840(10)
_cell_angle_gamma                90
_cell_volume                     1239.24(5)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-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'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            4

_chemical_formula_sum            'C9 H17 F6 N2 P1'
_chemical_formula_moiety         'C9 H17 N2, F6 P1'
_chemical_compound_source        synthesized
_chemical_formula_weight         298.21


_cell_measurement_reflns_used    11327
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      31.8
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.10

_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.282

_exptl_absorpt_correction_type   none
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.710918
_diffrn_measurement_method       'Omega scan'

_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_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      100
_diffrn_reflns_number            12339
_diffrn_reflns_av_unetI/netI     0.021
_reflns_number_total             3445
_diffrn_reflns_av_R_equivalents  0.021

_diffrn_reflns_theta_min         2.842
_diffrn_reflns_theta_max         31.801
_diffrn_measured_fraction_theta_max 0.814

_diffrn_reflns_theta_full        25.123
_diffrn_measured_fraction_theta_full 0.947

_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              39
_reflns_limit_l_min              0
_reflns_limit_l_max              11

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.31
_refine_diff_density_max         0.46

# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     4
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3445
_oxford_refine_ls_R_factor_ref   0.0366
_refine_ls_wR_factor_ref         0.0873
_refine_ls_goodness_of_fit_ref   0.9964
_refine_ls_shift/su_max          0.0021061
_refine_ls_shift/su_mean         0.0000821

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3445
_refine_ls_R_factor_all          0.0366
_refine_ls_wR_factor_all         0.0873

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3228
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_gt          0.0860

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.86P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
P1 P 0.24020(5) 0.648125(11) 0.21790(4) 0.0169 1.0000 Uani . . . . . .
F2 F -0.01204(13) 0.66218(4) 0.19751(11) 0.0343 1.0000 Uani . . . . . .
F3 F 0.17358(15) 0.61174(4) 0.04795(12) 0.0374 1.0000 Uani . . . . . .
F4 F 0.26746(16) 0.69405(3) 0.09086(13) 0.0376 1.0000 Uani . . . . . .
F5 F 0.49042(13) 0.63395(4) 0.24103(13) 0.0378 1.0000 Uani . . . . . .
F6 F 0.21131(16) 0.60195(4) 0.34752(13) 0.0399 1.0000 Uani . . . . . .
F7 F 0.30049(17) 0.68384(4) 0.39076(13) 0.0453 1.0000 Uani . . . . . .
N8 N 0.65261(16) 0.63771(3) 0.72996(12) 0.0161 1.0000 Uani . . . . . .
N9 N 0.92910(17) 0.65782(4) 0.59190(13) 0.0202 1.0000 Uani D . . . . .
C10 C 0.6449(2) 0.68973(4) 0.79818(16) 0.0199 1.0000 Uani . . . . . .
C11 C 0.78596(18) 0.62518(4) 0.62876(14) 0.0164 1.0000 Uani D . . . . .
C12 C 0.7300(2) 0.72731(4) 0.68212(16) 0.0215 1.0000 Uani . . . . . .
C13 C 0.51139(19) 0.60022(4) 0.78898(16) 0.0204 1.0000 Uani . . . . . .
C14 C 0.6384(2) 0.55947(4) 0.91227(16) 0.0221 1.0000 Uani . . . . . .
C15 C 0.7859(2) 0.57251(4) 0.55577(15) 0.0215 1.0000 Uani . . . . . .
C16 C 0.7225(2) 0.51676(4) 0.81291(17) 0.0246 1.0000 Uani . . . . . .
C17 C 0.8820(2) 0.53339(5) 0.70174(17) 0.0245 1.0000 Uani . . . . . .
C18 C 0.9504(2) 0.71004(4) 0.65747(17) 0.0234 1.0000 Uani D . . . . .
H102 H 0.7251 0.6915 0.9218 0.0230 1.0000 Uiso R . . . . .
H101 H 0.4944 0.6968 0.7965 0.0234 1.0000 Uiso R . . . . .
H122 H 0.7409 0.7605 0.7398 0.0245 1.0000 Uiso R . . . . .
H121 H 0.6260 0.7297 0.5632 0.0244 1.0000 Uiso R . . . . .
H132 H 0.4268 0.6195 0.8564 0.0235 1.0000 Uiso R . . . . .
H131 H 0.4130 0.5841 0.6811 0.0244 1.0000 Uiso R . . . . .
H142 H 0.7629 0.5757 0.9978 0.0262 1.0000 Uiso R . . . . .
H141 H 0.5406 0.5452 0.9794 0.0259 1.0000 Uiso R . . . . .
H152 H 0.8742 0.5736 0.4666 0.0257 1.0000 Uiso R . . . . .
H151 H 0.6317 0.5626 0.4983 0.0255 1.0000 Uiso R . . . . .
H162 H 0.7921 0.4909 0.8972 0.0305 1.0000 Uiso R . . . . .
H161 H 0.5935 0.5014 0.7307 0.0289 1.0000 Uiso R . . . . .
H172 H 1.0160 0.5479 0.7826 0.0287 1.0000 Uiso R . . . . .
H171 H 0.9240 0.5039 0.6410 0.0287 1.0000 Uiso R . . . . .
H182 H 0.9964 0.7304 0.5680 0.0273 1.0000 Uiso R . . . . .
H181 H 1.0579 0.7109 0.7727 0.0272 1.0000 Uiso R . . . . .
H91 H 1.003(3) 0.6484(5) 0.517(2) 0.0253(18) 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.391(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
P1 . F2 . 1.6014(8) yes
P1 . F3 . 1.5933(8) yes
P1 . F4 . 1.5915(9) yes
P1 . F5 . 1.5869(8) yes
P1 . F6 . 1.6119(9) yes
P1 . F7 . 1.5977(9) yes
N8 . C10 . 1.4764(14) yes
N8 . C11 . 1.3147(14) yes
N8 . C13 . 1.4731(14) yes
N9 . C11 . 1.3259(14) yes
N9 . C18 . 1.4645(15) yes
N9 . H91 . 0.854(13) no
C10 . C12 . 1.5149(16) yes
C10 . H102 . 0.963 no
C10 . H101 . 0.963 no
C11 . C15 . 1.5007(15) yes
C12 . C18 . 1.5146(17) yes
C12 . H122 . 0.978 no
C12 . H121 . 0.989 no
C13 . C14 . 1.5272(16) yes
C13 . H132 . 0.971 no
C13 . H131 . 1.002 no
C14 . C16 . 1.5261(17) yes
C14 . H142 . 0.991 no
C14 . H141 . 0.969 no
C15 . C17 . 1.5378(16) yes
C15 . H152 . 0.979 no
C15 . H151 . 1.000 no
C16 . C17 . 1.5292(18) yes
C16 . H162 . 0.971 no
C16 . H161 . 0.988 no
C17 . H172 . 0.996 no
C17 . H171 . 0.976 no
C18 . H182 . 0.969 no
C18 . H181 . 0.976 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
F2 . P1 . F3 . 89.97(5) yes
F2 . P1 . F4 . 90.73(5) yes
F3 . P1 . F4 . 90.31(5) yes
F2 . P1 . F5 . 179.17(5) yes
F3 . P1 . F5 . 90.51(5) yes
F4 . P1 . F5 . 89.95(5) yes
F2 . P1 . F6 . 88.88(5) yes
F3 . P1 . F6 . 90.06(5) yes
F4 . P1 . F6 . 179.46(5) yes
F5 . P1 . F6 . 90.44(5) yes
F2 . P1 . F7 . 88.68(5) yes
F3 . P1 . F7 . 178.10(5) yes
F4 . P1 . F7 . 91.04(6) yes
F5 . P1 . F7 . 90.83(6) yes
F6 . P1 . F7 . 88.58(6) yes
C10 . N8 . C11 . 121.59(9) yes
C10 . N8 . C13 . 116.39(9) yes
C11 . N8 . C13 . 121.95(9) yes
C11 . N9 . C18 . 123.46(10) yes
C11 . N9 . H91 . 117.3(9) no
C18 . N9 . H91 . 119.0(9) no
N8 . C10 . C12 . 110.88(9) yes
N8 . C10 . H102 . 109.8 no
C12 . C10 . H102 . 111.8 no
N8 . C10 . H101 . 107.0 no
C12 . C10 . H101 . 110.5 no
H102 . C10 . H101 . 106.6 no
N9 . C11 . N8 . 121.61(10) yes
N9 . C11 . C15 . 117.63(10) yes
N8 . C11 . C15 . 120.73(10) yes
C10 . C12 . C18 . 109.81(9) yes
C10 . C12 . H122 . 108.6 no
C18 . C12 . H122 . 111.1 no
C10 . C12 . H121 . 109.5 no
C18 . C12 . H121 . 109.2 no
H122 . C12 . H121 . 108.6 no
N8 . C13 . C14 . 113.58(9) yes
N8 . C13 . H132 . 105.0 no
C14 . C13 . H132 . 108.2 no
N8 . C13 . H131 . 109.4 no
C14 . C13 . H131 . 109.8 no
H132 . C13 . H131 . 110.7 no
C13 . C14 . C16 . 113.92(10) yes
C13 . C14 . H142 . 108.6 no
C16 . C14 . H142 . 109.7 no
C13 . C14 . H141 . 107.4 no
C16 . C14 . H141 . 108.5 no
H142 . C14 . H141 . 108.6 no
C11 . C15 . C17 . 112.80(9) yes
C11 . C15 . H152 . 106.4 no
C17 . C15 . H152 . 109.8 no
C11 . C15 . H151 . 108.7 no
C17 . C15 . H151 . 108.5 no
H152 . C15 . H151 . 110.7 no
C14 . C16 . C17 . 114.72(9) yes
C14 . C16 . H162 . 110.1 no
C17 . C16 . H162 . 108.8 no
C14 . C16 . H161 . 107.0 no
C17 . C16 . H161 . 108.1 no
H162 . C16 . H161 . 107.8 no
C15 . C17 . C16 . 113.76(10) yes
C15 . C17 . H172 . 108.7 no
C16 . C17 . H172 . 109.6 no
C15 . C17 . H171 . 107.1 no
C16 . C17 . H171 . 109.0 no
H172 . C17 . H171 . 108.6 no
C12 . C18 . N9 . 108.40(9) yes
C12 . C18 . H182 . 111.0 no
N9 . C18 . H182 . 107.4 no
C12 . C18 . H181 . 109.7 no
N9 . C18 . H181 . 108.7 no
H182 . C18 . H181 . 111.6 no

_iucr_refine_instructions_details_constraints 
;
#
# Punched on 04/01/19 at 15:34:52
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT P    (     1 ,X'S,U'S)  UNTIL C    (    18 ) 
CONT H    (    91 ,X'S,U[ISO]) 
RIDE C   (  10,X'S) H   ( 102,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 132,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 152,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 162,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 172,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 182,X'S) H   ( 181,X'S) 
END                                                                             
;

_iucr_refine_instructions_details_restraints 
;
#
# Punched on 04/01/19 at 15:34:52
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H  NO #H U MULT   DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM 
REM TO ACTIVATE THE VIB RESTRAINTS, REMOVE LEADING REM 
REM            H1-N-R2 
DIST 0.86, 0.02 = 
CONT N ( 9) TO H(91) 
REST 0.023, 0.002 = H(91,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(91) TO N ( 9) TO C(11) 
CONT H(91) TO N ( 9) TO C(18) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
