# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1836021'
_audit_update_record             
;
2018-08-01 deposited with the CCDC.
2018-08-07 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          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

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

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

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

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   13.898(2)
_cell_length_b                   12.655(3)
_cell_length_c                   14.221(3)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     2501.0(9)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 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'
Zn 0.2839 1.4301 14.0743 3.2655 7.0318 0.2333 5.1652 10.3163 2.4100 58.7097
1.3041 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C20 H23 N9 O5 S2 Zn1 
# Dc =      1.59 Fooo =   1232.00 Mu =     12.01 M =    598.97
# Found Formula = C20 H23 N9 O5 S2 Zn1 
# Dc =      1.59 FOOO =   1232.00 Mu =     12.01 M =    598.97

_chemical_formula_sum            'C20 H23 N9 O5 S2 Zn1'
_chemical_formula_moiety         'C20 H23 N9 O5 S2 Zn1'
_chemical_compound_source        ?
_chemical_formula_weight         598.97


_cell_measurement_reflns_used    3457
_cell_measurement_theta_min      3.5171
_cell_measurement_theta_max      29.4458
_cell_measurement_temperature    293

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.105
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_max          0.119

_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    1.201

# Sheldrick geometric approximatio 0.87 0.88 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_T_max  0.88
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      293
_diffrn_reflns_number            7690
_reflns_number_total             4563
_diffrn_reflns_av_R_equivalents  0.029
# Number of reflections without Friedels Law is 4563 
# Number of reflections with Friedels Law is 3150 
# Theoretical number of reflections is about 3484 


_diffrn_reflns_theta_min         3.538
_diffrn_reflns_theta_max         29.509
_diffrn_measured_fraction_theta_max 0.969

_diffrn_reflns_theta_full        25.082
_diffrn_measured_fraction_theta_full 0.988


_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              0
_reflns_limit_h_max              19
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              -13
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.82
_refine_diff_density_max         0.32


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>1.0\s(I)
_refine_ls_number_reflns         3458
_refine_ls_number_restraints     1
_refine_ls_number_parameters     335
_oxford_refine_ls_R_factor_ref   0.0508
_refine_ls_wR_factor_ref         0.0660
_refine_ls_goodness_of_fit_ref   1.0607
_refine_ls_shift/su_max          0.0001906
_refine_ls_shift/su_mean         0.0000157


# The values computed from all data 
_oxford_reflns_number_all        4556
_refine_ls_R_factor_all          0.0701
_refine_ls_wR_factor_all         0.0860

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2998
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_gt          0.0611

_refine_ls_abs_structure_Flack   0.11(2)
_refine_ls_abs_structure_details 'Flack (1983), 1413 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 17.7 -4.93 14.9 
;

# 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
Zn1 Zn 0.74222(4) 0.07753(5) 0.66509(10) 0.0548 1.0000 Uani . . . . . .
N1 N 0.7512(3) -0.0999(4) 0.6036(4) 0.0495 1.0000 Uani . . . . . .
C2 C 0.7552(4) -0.1697(6) 0.5337(5) 0.0617 1.0000 Uani . . . . . .
C3 C 0.7430(4) -0.2746(6) 0.5484(5) 0.0627 1.0000 Uani . . . . . .
C4 C 0.7261(4) -0.3068(5) 0.6391(4) 0.0562 1.0000 Uani . . . . . .
N5 N 0.7199(3) -0.2409(4) 0.7118(3) 0.0493 1.0000 Uani . . . . . .
C6 C 0.7345(3) -0.1388(4) 0.6917(4) 0.0409 1.0000 Uani . . . . . .
N7 N 0.7350(3) -0.0604(4) 0.7571(4) 0.0470 1.0000 Uani . . . . . .
S8 S 0.69997(9) -0.07410(10) 0.86335(12) 0.0468 1.0000 Uani . . . . . .
O9 O 0.7257(3) 0.0239(3) 0.9092(3) 0.0584 1.0000 Uani . . . . . .
O10 O 0.7335(3) -0.1700(3) 0.9079(3) 0.0573 1.0000 Uani . . . . . .
C11 C 0.5733(3) -0.0784(4) 0.8597(4) 0.0441 1.0000 Uani . . . . . .
C12 C 0.5250(4) -0.1743(4) 0.8650(4) 0.0484 1.0000 Uani . . . . . .
C13 C 0.4258(4) -0.1758(4) 0.8621(4) 0.0515 1.0000 Uani . . . . . .
C14 C 0.3735(4) -0.0820(4) 0.8541(4) 0.0441 1.0000 Uani . . . . . .
N15 N 0.2736(3) -0.0856(4) 0.8555(4) 0.0577 1.0000 Uani . . . . . .
C16 C 0.4220(4) 0.0133(4) 0.8501(4) 0.0476 1.0000 Uani . . . . . .
C17 C 0.5219(4) 0.0150(4) 0.8525(4) 0.0459 1.0000 Uani . . . . . .
N21 N 0.5971(3) 0.0832(3) 0.6294(3) 0.0438 1.0000 Uani . . . . . .
C22 C 0.5386(4) 0.0063(4) 0.6004(4) 0.0521 1.0000 Uani . . . . . .
C23 C 0.4406(4) 0.0221(4) 0.5930(4) 0.0544 1.0000 Uani . . . . . .
C24 C 0.4069(4) 0.1200(5) 0.6150(4) 0.0535 1.0000 Uani . . . . . .
N25 N 0.4633(3) 0.2015(3) 0.6417(3) 0.0508 1.0000 Uani . . . . . .
C26 C 0.5579(3) 0.1783(4) 0.6501(4) 0.0443 1.0000 Uani . . . . . .
N27 N 0.6251(3) 0.2508(4) 0.6784(4) 0.0557 1.0000 Uani . . . . . .
S28 S 0.59881(10) 0.34852(10) 0.74059(12) 0.0527 1.0000 Uani . . . . . .
O29 O 0.5233(3) 0.3288(3) 0.8088(3) 0.0645 1.0000 Uani . . . . . .
O30 O 0.6901(3) 0.3837(4) 0.7812(4) 0.0715 1.0000 Uani . . . . . .
C31 C 0.5576(4) 0.4525(4) 0.6686(4) 0.0483 1.0000 Uani . . . . . .
C32 C 0.5783(4) 0.4556(5) 0.5734(4) 0.0539 1.0000 Uani . . . . . .
C33 C 0.5521(4) 0.5429(5) 0.5201(4) 0.0558 1.0000 Uani . . . . . .
C34 C 0.5061(4) 0.6295(4) 0.5620(4) 0.0520 1.0000 Uani . . . . . .
N35 N 0.4844(4) 0.7201(4) 0.5114(5) 0.0699 1.0000 Uani . . . . . .
C36 C 0.4843(4) 0.6244(4) 0.6571(5) 0.0574 1.0000 Uani . . . . . .
C37 C 0.5094(4) 0.5376(5) 0.7097(4) 0.0559 1.0000 Uani . . . . . .
N41 N 0.8089(4) 0.1687(4) 0.7647(4) 0.0620 1.0000 Uani . . . . . .
O42 O 0.8210(4) 0.1230(5) 0.5516(4) 0.0976 1.0000 Uani . . . . . .
H21 H 0.7667 -0.1445 0.4727 0.0732 1.0000 Uiso R . . . . .
H31 H 0.7462 -0.3232 0.4991 0.0741 1.0000 Uiso R . . . . .
H41 H 0.7175 -0.3782 0.6502 0.0670 1.0000 Uiso R . . . . .
H121 H 0.5598 -0.2372 0.8706 0.0568 1.0000 Uiso R . . . . .
H131 H 0.3933 -0.2399 0.8664 0.0610 1.0000 Uiso R . . . . .
H161 H 0.3878 0.0767 0.8455 0.0564 1.0000 Uiso R . . . . .
H171 H 0.5550 0.0788 0.8495 0.0556 1.0000 Uiso R . . . . .
H221 H 0.5642 -0.0604 0.5853 0.0621 1.0000 Uiso R . . . . .
H231 H 0.3994 -0.0324 0.5744 0.0650 1.0000 Uiso R . . . . .
H241 H 0.3409 0.1333 0.6105 0.0646 1.0000 Uiso R . . . . .
H321 H 0.6102 0.3986 0.5443 0.0641 1.0000 Uiso R . . . . .
H331 H 0.5654 0.5445 0.4553 0.0672 1.0000 Uiso R . . . . .
H361 H 0.4529 0.6811 0.6864 0.0680 1.0000 Uiso R . . . . .
H371 H 0.4935 0.5348 0.7734 0.0660 1.0000 Uiso R . . . . .
H152 H 0.2448 -0.1403 0.8327 0.0681 1.0000 Uiso R . . . . .
H151 H 0.2421 -0.0322 0.8335 0.0683 1.0000 Uiso R . . . . .
H421 H 0.8627 0.1693 0.5527 0.1460 1.0000 Uiso R . . . . .
H412 H 0.8720 0.1686 0.7548 0.0950 1.0000 Uiso R . . . . .
H351 H 0.4807 0.7171 0.4518 0.0833 1.0000 Uiso R . . . . .
H411 H 0.7872 0.2343 0.7604 0.0954 1.0000 Uiso R . . . . .
H413 H 0.7967 0.1432 0.8221 0.0951 1.0000 Uiso R . . . . .
H352 H 0.5454 0.7567 0.5170 0.0829 1.0000 Uiso R . . . . .
H422 H 0.8071 0.0903 0.4917 0.1171 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.571(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
Zn1 . N1 . 2.413(5) yes
Zn1 . N7 . 2.185(5) yes
Zn1 . N21 . 2.081(4) yes
Zn1 . N27 . 2.738(5) yes
Zn1 . N41 . 2.049(5) yes
Zn1 . O42 . 2.034(6) yes
N1 . C2 . 1.331(9) yes
N1 . C6 . 1.367(8) yes
C2 . C3 . 1.354(10) yes
C2 . H21 . 0.939 no
C3 . C4 . 1.372(10) yes
C3 . H31 . 0.934 no
C4 . N5 . 1.331(7) yes
C4 . H41 . 0.925 no
N5 . C6 . 1.338(7) yes
C6 . N7 . 1.360(7) yes
N7 . S8 . 1.596(6) yes
S8 . O9 . 1.446(4) yes
S8 . O10 . 1.447(4) yes
S8 . C11 . 1.762(5) yes
C11 . C12 . 1.389(7) yes
C11 . C17 . 1.385(7) yes
C12 . C13 . 1.379(8) yes
C12 . H121 . 0.935 no
C13 . C14 . 1.396(7) yes
C13 . H131 . 0.931 no
C14 . N15 . 1.390(7) yes
C14 . C16 . 1.382(7) yes
N15 . H152 . 0.862 no
N15 . H151 . 0.864 no
C16 . C17 . 1.389(7) yes
C16 . H161 . 0.936 no
C17 . H171 . 0.931 no
N21 . C22 . 1.334(7) yes
N21 . C26 . 1.354(6) yes
C22 . C23 . 1.380(8) yes
C22 . H221 . 0.940 no
C23 . C24 . 1.362(8) yes
C23 . H231 . 0.935 no
C24 . N25 . 1.350(7) yes
C24 . H241 . 0.934 no
N25 . C26 . 1.352(6) yes
C26 . N27 . 1.369(7) yes
N27 . S28 . 1.563(5) yes
S28 . O29 . 1.450(5) yes
S28 . O30 . 1.464(4) yes
S28 . C31 . 1.762(6) yes
C31 . C32 . 1.385(9) yes
C31 . C37 . 1.396(8) yes
C32 . C33 . 1.389(9) yes
C32 . H321 . 0.942 no
C33 . C34 . 1.402(8) yes
C33 . H331 . 0.939 no
C34 . N35 . 1.387(8) yes
C34 . C36 . 1.387(10) yes
N35 . H351 . 0.851 no
N35 . H352 . 0.969 no
C36 . C37 . 1.375(9) yes
C36 . H361 . 0.937 no
C37 . H371 . 0.934 no
N41 . H412 . 0.889 no
N41 . H411 . 0.885 no
N41 . H413 . 0.893 no
O42 . H421 . 0.824 no
O42 . H422 . 0.966 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
N1 . Zn1 . N7 . 58.4(2) yes
N1 . Zn1 . N21 . 89.66(15) yes
N7 . Zn1 . N21 . 97.42(17) yes
N1 . Zn1 . N27 . 143.25(15) yes
N7 . Zn1 . N27 . 124.85(17) yes
N21 . Zn1 . N27 . 54.04(14) yes
N1 . Zn1 . N41 . 138.7(2) yes
N7 . Zn1 . N41 . 93.2(2) yes
N21 . Zn1 . N41 . 125.98(19) yes
N27 . Zn1 . N41 . 76.70(18) yes
N1 . Zn1 . O42 . 87.0(2) yes
N7 . Zn1 . O42 . 136.6(2) yes
N21 . Zn1 . O42 . 108.6(2) yes
N27 . Zn1 . O42 . 98.5(2) yes
N41 . Zn1 . O42 . 98.4(2) yes
Zn1 . N1 . C2 . 153.0(5) yes
Zn1 . N1 . C6 . 89.7(3) yes
C2 . N1 . C6 . 116.8(5) yes
N1 . C2 . C3 . 122.1(6) yes
N1 . C2 . H21 . 118.1 no
C3 . C2 . H21 . 119.8 no
C2 . C3 . C4 . 117.2(6) yes
C2 . C3 . H31 . 121.5 no
C4 . C3 . H31 . 121.2 no
C3 . C4 . N5 . 123.7(6) yes
C3 . C4 . H41 . 118.3 no
N5 . C4 . H41 . 118.1 no
C4 . N5 . C6 . 115.4(5) yes
N1 . C6 . N5 . 124.7(5) yes
N1 . C6 . N7 . 111.3(5) yes
N5 . C6 . N7 . 124.0(5) yes
Zn1 . N7 . C6 . 100.0(4) yes
Zn1 . N7 . S8 . 131.9(3) yes
C6 . N7 . S8 . 124.5(4) yes
N7 . S8 . O9 . 105.0(3) yes
N7 . S8 . O10 . 114.0(3) yes
O9 . S8 . O10 . 116.3(3) yes
N7 . S8 . C11 . 106.2(3) yes
O9 . S8 . C11 . 106.7(2) yes
O10 . S8 . C11 . 108.0(2) yes
S8 . C11 . C12 . 120.6(4) yes
S8 . C11 . C17 . 119.4(4) yes
C12 . C11 . C17 . 120.0(5) yes
C11 . C12 . C13 . 119.6(4) yes
C11 . C12 . H121 . 119.9 no
C13 . C12 . H121 . 120.5 no
C12 . C13 . C14 . 120.7(5) yes
C12 . C13 . H131 . 119.7 no
C14 . C13 . H131 . 119.6 no
C13 . C14 . N15 . 119.4(5) yes
C13 . C14 . C16 . 119.4(5) yes
N15 . C14 . C16 . 121.0(5) yes
C14 . N15 . H152 . 119.0 no
C14 . N15 . H151 . 118.4 no
H152 . N15 . H151 . 104.9 no
C14 . C16 . C17 . 120.0(5) yes
C14 . C16 . H161 . 120.3 no
C17 . C16 . H161 . 119.8 no
C16 . C17 . C11 . 120.3(5) yes
C16 . C17 . H171 . 120.5 no
C11 . C17 . H171 . 119.2 no
Zn1 . N21 . C22 . 129.8(3) yes
Zn1 . N21 . C26 . 111.6(3) yes
C22 . N21 . C26 . 118.1(4) yes
N21 . C22 . C23 . 121.3(5) yes
N21 . C22 . H221 . 119.7 no
C23 . C22 . H221 . 119.1 no
C22 . C23 . C24 . 117.0(5) yes
C22 . C23 . H231 . 121.3 no
C24 . C23 . H231 . 121.7 no
C23 . C24 . N25 . 124.0(5) yes
C23 . C24 . H241 . 119.1 no
N25 . C24 . H241 . 116.9 no
C24 . N25 . C26 . 115.1(4) yes
N21 . C26 . N25 . 124.4(4) yes
N21 . C26 . N27 . 112.7(4) yes
N25 . C26 . N27 . 123.0(4) yes
C26 . N27 . Zn1 . 81.3(3) yes
C26 . N27 . S28 . 122.4(4) yes
Zn1 . N27 . S28 . 144.2(3) yes
N27 . S28 . O29 . 114.3(3) yes
N27 . S28 . O30 . 105.1(3) yes
O29 . S28 . O30 . 114.6(3) yes
N27 . S28 . C31 . 109.7(3) yes
O29 . S28 . C31 . 106.4(3) yes
O30 . S28 . C31 . 106.5(3) yes
S28 . C31 . C32 . 121.5(4) yes
S28 . C31 . C37 . 119.2(5) yes
C32 . C31 . C37 . 119.1(6) yes
C31 . C32 . C33 . 120.1(5) yes
C31 . C32 . H321 . 120.3 no
C33 . C32 . H321 . 119.6 no
C32 . C33 . C34 . 120.6(6) yes
C32 . C33 . H331 . 120.0 no
C34 . C33 . H331 . 119.4 no
C33 . C34 . N35 . 121.6(6) yes
C33 . C34 . C36 . 118.6(6) yes
N35 . C34 . C36 . 119.7(5) yes
C34 . N35 . H351 . 119.6 no
C34 . N35 . H352 . 99.3 no
H351 . N35 . H352 . 98.9 no
C34 . C36 . C37 . 120.7(5) yes
C34 . C36 . H361 . 120.0 no
C37 . C36 . H361 . 119.3 no
C31 . C37 . C36 . 120.8(6) yes
C31 . C37 . H371 . 119.4 no
C36 . C37 . H371 . 119.8 no
Zn1 . N41 . H412 . 109.6 no
Zn1 . N41 . H411 . 109.0 no
H412 . N41 . H411 . 109.1 no
Zn1 . N41 . H413 . 110.0 no
H412 . N41 . H413 . 109.4 no
H411 . N41 . H413 . 109.8 no
Zn1 . O42 . H421 . 124.3 no
Zn1 . O42 . H422 . 118.1 no
H421 . O42 . H422 . 117.6 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C3 . H31 . O9 2_644 163.3 0.934 2.352 3.257(8) yes
C13 . H131 . O10 3_445 145.37 0.931 2.565 3.372(8) yes
N15 . H152 . N5 3_445 150.64 0.862 2.311 3.091(8) yes
N15 . H151 . O30 3_455 168.85 0.864 2.147 2.999(8) yes
O42 . H421 . N25 3_555 150.44 0.824 2.496 3.238(8) yes
N41 . H412 . O29 3_555 150.73 0.889 2.239 3.045(8) yes
N35 . H351 . O29 4_664 166.49 0.851 2.116 2.950(8) yes
N41 . H411 . O30 . 161.0 0.885 2.342 3.191(8) yes
N41 . H413 . O9 . 148.0 0.893 2.188 2.986(8) yes
O42 . H422 . N15 4_654 150.8 0.966 2.239 3.119(8) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 23/04/12 at 11:15:33
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
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   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE N   (  15,X'S) H   ( 152,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   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE N   (  35,X'S) H   ( 351,X'S) H   ( 352,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE N   (  41,X'S) H   ( 412,X'S) H   ( 411,X'S) H   ( 413,X'S) 
RIDE O   (  42,X'S) H   ( 421,X'S) H   ( 422,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 23/04/12 at 11:15:33
#
#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
4 0 13 x .
4 0 12 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1836022'
_audit_update_record             
;
2018-08-01 deposited with the CCDC.
2018-08-07 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          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

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

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

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

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   12.6714(6)
_cell_length_b                   14.1042(7)
_cell_length_c                   15.0668(7)
_cell_angle_alpha                68.569(5)
_cell_angle_beta                 81.395(4)
_cell_angle_gamma                77.993(4)
_cell_volume                     2443.7(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'
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'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Zn 0.2839 1.4301 14.0743 3.2655 7.0318 0.2333 5.1652 10.3163 2.4100 58.7097
1.3041 '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'
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'


_cell_formula_units_Z            2

# Given Formula = C30 H25 Cl1 F2 N10 O8 S1 Zn1 
# Dc =      1.12 Fooo =   1176.00 Mu =      6.54 M =    824.49
# Found Formula = C48 H53 Cl1 F2 N10 O12 S1 Zn1 
# Dc =      1.54 FOOO =   1176.00 Mu =      6.83 M =   1132.90

_chemical_formula_sum            'C48 H53 Cl1 F2 N10 O12 S1 Zn1'
_chemical_formula_moiety         'C48 H53 Cl1 F2 N10 O12 S1 Zn1'
_chemical_compound_source        ?
_chemical_formula_weight         1132.90


_cell_measurement_reflns_used    10772
_cell_measurement_theta_min      3
_cell_measurement_theta_max      29
_cell_measurement_temperature    293

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.091
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_max          0.504

_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    0.683

# Sheldrick geometric approximatio 0.79 0.94 
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.94
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      293
_diffrn_reflns_number            23105
_reflns_number_total             11457
_diffrn_reflns_av_R_equivalents  0.039
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 11457 
# Theoretical number of reflections is about 26788 


_diffrn_reflns_theta_min         2.643
_diffrn_reflns_theta_max         29.585
_diffrn_measured_fraction_theta_max 0.934

_diffrn_reflns_theta_full        25.147
_diffrn_measured_fraction_theta_full 0.988


_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -17
_reflns_limit_h_max              17
_reflns_limit_k_min              -17
_reflns_limit_k_max              19
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -2.20
_refine_diff_density_max         1.41


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>5.0\s(I)
_refine_ls_number_reflns         6733
_refine_ls_number_restraints     12
_refine_ls_number_parameters     677
_oxford_refine_ls_R_factor_ref   0.0966
_refine_ls_wR_factor_ref         0.0938
_refine_ls_goodness_of_fit_ref   1.0228
_refine_ls_shift/su_max          0.0003578
_refine_ls_shift/su_mean         0.0000118


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        11382
_refine_ls_R_factor_all          0.1241
_refine_ls_wR_factor_all         0.1012

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                9359
_refine_ls_R_factor_gt           0.1100
_refine_ls_wR_factor_gt          0.0979

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


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #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: 
 12.7 3.40 9.83 3.42 
;

# 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
Zn1 Zn 0.33003(5) 0.46694(6) 0.76130(5) 0.0266 1.0000 Uani . . . . . .
O2 O 0.4651(3) 0.4715(4) 0.8269(3) 0.0331 1.0000 Uani . . . . . .
C3 C 0.4711(4) 0.5399(4) 0.8603(4) 0.0221 1.0000 Uani . . . . . .
C4 C 0.5751(4) 0.5499(4) 0.8810(4) 0.0235 1.0000 Uani . . . . . .
C5 C 0.5900(4) 0.6251(5) 0.9155(4) 0.0266 1.0000 Uani . . . . . .
N6 N 0.4986(4) 0.6926(4) 0.9329(4) 0.0360 1.0000 Uani . . . . . .
C7 C 0.4002(4) 0.6850(5) 0.9143(5) 0.0363 1.0000 Uani . . . . . .
C8 C 0.3813(4) 0.6138(5) 0.8787(4) 0.0280 1.0000 Uani . . . . . .
C9 C 0.2653(4) 0.6173(5) 0.8648(5) 0.0319 1.0000 Uani . . . . . .
O10 O 0.2418(3) 0.5560(4) 0.8303(4) 0.0410 1.0000 Uani . . . . . .
O11 O 0.1973(4) 0.6812(4) 0.8891(4) 0.0506 1.0000 Uani . . . . . .
C12 C 0.5055(6) 0.7636(6) 0.9832(7) 0.0505 1.0000 Uani . . . . . .
C13 C 0.5566(7) 0.8541(8) 0.9310(11) 0.0855 1.0000 Uani . . . . . .
C14 C 0.4368(6) 0.8644(7) 0.9534(8) 0.0624 1.0000 Uani . . . . . .
C15 C 0.6937(5) 0.6346(5) 0.9301(5) 0.0346 1.0000 Uani . . . . . .
C16 C 0.7838(4) 0.5691(5) 0.9146(4) 0.0268 1.0000 Uani . . . . . .
N17 N 0.8890(4) 0.5744(4) 0.9276(4) 0.0312 1.0000 Uani . . . . . .
C18 C 0.9804(5) 0.5617(5) 0.8565(5) 0.0383 1.0000 Uani . . . . . .
C19 C 0.9859(5) 0.6646(5) 0.7744(5) 0.0382 1.0000 Uani . . . . . .
N20 N 1.0075(4) 0.7411(4) 0.8147(4) 0.0345 1.0000 Uani . . . . . .
C21 C 0.9187(5) 0.7533(5) 0.8899(5) 0.0367 1.0000 Uani . . . . . .
C22 C 0.9071(5) 0.6502(5) 0.9661(5) 0.0322 1.0000 Uani . . . . . .
C23 C 1.0200(6) 0.8435(6) 0.7408(7) 0.0541 1.0000 Uani . . . . . .
C24 C 1.1109(9) 0.8363(8) 0.6644(9) 0.0899 1.0000 Uani . . . . . .
C25 C 0.7662(4) 0.4868(5) 0.8876(4) 0.0265 1.0000 Uani . . . . . .
C26 C 0.6671(4) 0.4780(5) 0.8705(4) 0.0241 1.0000 Uani . . . . . .
F27 F 0.8513(3) 0.4126(3) 0.8823(3) 0.0392 1.0000 Uani . . . . . .
O29 O 0.3872(3) 0.5598(4) 0.6350(3) 0.0398 1.0000 Uani . . . . . .
C30 C 0.3421(4) 0.6175(5) 0.5613(5) 0.0308 1.0000 Uani . . . . . .
C31 C 0.2250(4) 0.6182(5) 0.5551(4) 0.0248 1.0000 Uani . . . . . .
C32 C 0.1766(4) 0.6947(5) 0.4783(4) 0.0280 1.0000 Uani . . . . . .
N33 N 0.0734(4) 0.7067(4) 0.4617(3) 0.0276 1.0000 Uani . . . . . .
C34 C 0.0079(4) 0.6364(4) 0.5201(4) 0.0238 1.0000 Uani . . . . . .
C35 C -0.0994(4) 0.6452(4) 0.5004(4) 0.0249 1.0000 Uani . . . . . .
C36 C -0.1640(4) 0.5752(4) 0.5569(4) 0.0243 1.0000 Uani . . . . . .
N37 N -0.2684(4) 0.5784(4) 0.5364(4) 0.0308 1.0000 Uani . . . . . .
C38 C -0.3079(5) 0.6514(5) 0.4465(4) 0.0331 1.0000 Uani . . . . . .
C39 C -0.3588(5) 0.7550(5) 0.4546(5) 0.0342 1.0000 Uani . . . . . .
N40 N -0.4492(4) 0.7438(4) 0.5323(4) 0.0338 1.0000 Uani . . . . . .
C41 C -0.4065(5) 0.6696(5) 0.6243(5) 0.0358 1.0000 Uani . . . . . .
C42 C -0.3567(5) 0.5663(5) 0.6120(5) 0.0359 1.0000 Uani . . . . . .
C43 C -0.5004(7) 0.8481(7) 0.5387(7) 0.0571 1.0000 Uani . . . . . .
C44 C -0.5953(9) 0.8417(9) 0.6107(10) 0.0853 1.0000 Uani . . . . . .
C45 C -0.1158(4) 0.4909(4) 0.6346(4) 0.0244 1.0000 Uani . . . . . .
F46 F -0.1732(3) 0.4153(3) 0.6857(3) 0.0365 1.0000 Uani . . . . . .
C47 C -0.0140(4) 0.4819(4) 0.6561(4) 0.0243 1.0000 Uani . . . . . .
C48 C 0.0526(4) 0.5550(4) 0.5993(4) 0.0227 1.0000 Uani . . . . . .
C49 C 0.1626(4) 0.5447(4) 0.6221(4) 0.0204 1.0000 Uani . . . . . .
O50 O 0.1951(3) 0.4750(3) 0.6969(3) 0.0294 1.0000 Uani . . . . . .
C51 C 0.0284(5) 0.7889(5) 0.3771(5) 0.0354 1.0000 Uani . . . . . .
C52 C -0.0504(6) 0.8780(6) 0.3922(6) 0.0497 1.0000 Uani . . . . . .
C53 C 0.0620(6) 0.8910(6) 0.3451(7) 0.0593 1.0000 Uani . . . . . .
O54 O 0.3901(4) 0.6759(4) 0.4897(3) 0.0486 1.0000 Uani . . . . . .
N55 N 0.4034(4) 0.3197(4) 0.7735(4) 0.0303 1.0000 Uani . . . . . .
C56 C 0.3461(5) 0.2402(5) 0.8109(4) 0.0328 1.0000 Uani . . . . . .
N57 N 0.2453(4) 0.2658(4) 0.8482(4) 0.0326 1.0000 Uani . . . . . .
S58 S 0.15166(12) 0.21047(13) 0.84130(12) 0.0357 1.0000 Uani . . . . . .
C60 C 0.1656(5) 0.0841(5) 0.9260(5) 0.0338 1.0000 Uani . . . . . .
C61 C 0.2047(5) 0.0633(5) 1.0121(5) 0.0341 1.0000 Uani . . . . . .
C62 C 0.2075(6) -0.0350(6) 1.0835(5) 0.0418 1.0000 Uani . . . . . .
C63 C 0.1706(6) -0.1122(6) 1.0657(6) 0.0461 1.0000 Uani . . . . . .
N64 N 0.1792(7) -0.2108(6) 1.1339(6) 0.0729 1.0000 Uani . . . . . .
C65 C 0.1357(8) -0.0926(7) 0.9780(7) 0.0597 1.0000 Uani . . . . . .
C66 C 0.1301(7) 0.0060(6) 0.9075(7) 0.0542 1.0000 Uani . . . . . .
O67 O 0.0520(4) 0.2664(4) 0.8710(5) 0.0562 1.0000 Uani . . . . . .
O68 O 0.1543(5) 0.2027(5) 0.7484(4) 0.0551 1.0000 Uani . . . . . .
N69 N 0.3876(5) 0.1438(5) 0.8117(5) 0.0501 1.0000 Uani . . . . . .
C70 C 0.4908(7) 0.1260(6) 0.7778(6) 0.0530 1.0000 Uani . . . . . .
C71 C 0.5544(6) 0.2011(7) 0.7416(6) 0.0539 1.0000 Uani . . . . . .
C72 C 0.5080(6) 0.2984(6) 0.7401(6) 0.0454 1.0000 Uani . . . . . .
Cl73 Cl 0.7118(2) -0.0684(2) 0.6613(2) 0.0814 1.0000 Uani . U . . . .
O74 O 0.7457(7) -0.0467(9) 0.7349(7) 0.1096 1.0000 Uani . . . . . .
O75 O 0.5989(7) -0.0502(10) 0.6631(9) 0.1320 1.0000 Uani . . . . . .
O76 O 0.7479(6) -0.1722(6) 0.6780(6) 0.0864 1.0000 Uani . U . . . .
O14 O 0.7596(6) -0.0087(7) 0.5722(6) 0.0883 1.0000 Uani . U . . . .
H71 H 0.3412 0.7313 0.9261 0.0437 1.0000 Uiso R . . . . .
H121 H 0.5196 0.7314 1.0512 0.0631 1.0000 Uiso R . . . . .
H132 H 0.6009 0.8778 0.9631 0.1039 1.0000 Uiso R . . . . .
H131 H 0.5858 0.8653 0.8647 0.1041 1.0000 Uiso R . . . . .
H141 H 0.4039 0.8984 0.9995 0.0732 1.0000 Uiso R . . . . .
H142 H 0.3894 0.8831 0.9032 0.0731 1.0000 Uiso R . . . . .
H151 H 0.7003 0.6871 0.9525 0.0398 1.0000 Uiso R . . . . .
H181 H 1.0464 0.5381 0.8869 0.0515 1.0000 Uiso R . . . . .
H182 H 0.9703 0.5121 0.8297 0.0523 1.0000 Uiso R . . . . .
H191 H 1.0435 0.6563 0.7266 0.0460 1.0000 Uiso R . . . . .
H192 H 0.9166 0.6881 0.7453 0.0460 1.0000 Uiso R . . . . .
H212 H 0.9370 0.7980 0.9187 0.0455 1.0000 Uiso R . . . . .
H211 H 0.8512 0.7837 0.8590 0.0449 1.0000 Uiso R . . . . .
H221 H 0.9717 0.6222 1.0003 0.0402 1.0000 Uiso R . . . . .
H222 H 0.8458 0.6605 1.0113 0.0398 1.0000 Uiso R . . . . .
H232 H 1.0336 0.8875 0.7723 0.0652 1.0000 Uiso R . . . . .
H231 H 0.9532 0.8720 0.7093 0.0648 1.0000 Uiso R . . . . .
H241 H 1.1211 0.9046 0.6228 0.1279 1.0000 Uiso R . . . . .
H243 H 1.1778 0.8018 0.6948 0.1279 1.0000 Uiso R . . . . .
H242 H 1.0961 0.7982 0.6283 0.1281 1.0000 Uiso R . . . . .
H261 H 0.6610 0.4240 0.8508 0.0320 1.0000 Uiso R . . . . .
H321 H 0.2180 0.7414 0.4355 0.0354 1.0000 Uiso R . . . . .
H351 H -0.1268 0.7005 0.4487 0.0298 1.0000 Uiso R . . . . .
H381 H -0.3599 0.6240 0.4270 0.0389 1.0000 Uiso R . . . . .
H382 H -0.2473 0.6615 0.3990 0.0390 1.0000 Uiso R . . . . .
H391 H -0.3039 0.7835 0.4699 0.0410 1.0000 Uiso R . . . . .
H392 H -0.3871 0.8010 0.3946 0.0407 1.0000 Uiso R . . . . .
H411 H -0.4647 0.6591 0.6741 0.0430 1.0000 Uiso R . . . . .
H412 H -0.3518 0.6964 0.6417 0.0431 1.0000 Uiso R . . . . .
H421 H -0.3264 0.5220 0.6711 0.0427 1.0000 Uiso R . . . . .
H422 H -0.4099 0.5356 0.5976 0.0429 1.0000 Uiso R . . . . .
H432 H -0.4466 0.8764 0.5570 0.0710 1.0000 Uiso R . . . . .
H431 H -0.5236 0.8932 0.4769 0.0708 1.0000 Uiso R . . . . .
H441 H -0.6356 0.9087 0.6008 0.1440 1.0000 Uiso R . . . . .
H443 H -0.5700 0.8126 0.6744 0.1439 1.0000 Uiso R . . . . .
H442 H -0.6398 0.7968 0.6041 0.1440 1.0000 Uiso R . . . . .
H471 H 0.0127 0.4277 0.7095 0.0289 1.0000 Uiso R . . . . .
H511 H 0.0145 0.7671 0.3263 0.0439 1.0000 Uiso R . . . . .
H521 H -0.0683 0.8809 0.4559 0.0599 1.0000 Uiso R . . . . .
H522 H -0.1115 0.9062 0.3546 0.0601 1.0000 Uiso R . . . . .
H531 H 0.1139 0.9028 0.3791 0.0738 1.0000 Uiso R . . . . .
H532 H 0.0706 0.9313 0.2783 0.0739 1.0000 Uiso R . . . . .
H611 H 0.2283 0.1161 1.0239 0.0426 1.0000 Uiso R . . . . .
H621 H 0.2339 -0.0479 1.1416 0.0510 1.0000 Uiso R . . . . .
H651 H 0.1122 -0.1453 0.9661 0.0740 1.0000 Uiso R . . . . .
H661 H 0.1022 0.0189 0.8492 0.0670 1.0000 Uiso R . . . . .
H701 H 0.5215 0.0595 0.7794 0.0660 1.0000 Uiso R . . . . .
H711 H 0.6265 0.1875 0.7178 0.0648 1.0000 Uiso R . . . . .
H721 H 0.5493 0.3520 0.7140 0.0552 1.0000 Uiso R . . . . .
H100 H 0.4418 0.6972 0.5034 0.0598 0.5000 Uiso R . . . . .
H641 H 0.2103 -0.2249 1.1927 0.0891 1.0000 Uiso R . . . . .
H642 H 0.1541 -0.2645 1.1238 0.0891 1.0000 Uiso R . . . . .
H571 H 0.2308 0.3247 0.8045 0.0420 1.0000 Uiso R . . . . .
H113 H 0.2137 0.7491 0.8535 0.0653 0.5000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.543(5)

loop_
_oxford_twin_element_scale_factors
0.687(3)
0.313(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
Zn1 . O2 . 2.124(4) yes
Zn1 . O10 . 1.983(4) yes
Zn1 . O29 . 2.006(4) yes
Zn1 . O50 . 2.052(4) yes
Zn1 . N55 . 2.045(5) yes
O2 . C3 . 1.258(7) yes
C3 . C4 . 1.444(7) yes
C3 . C8 . 1.443(8) yes
C4 . C5 . 1.396(8) yes
C4 . C26 . 1.408(8) yes
C5 . N6 . 1.396(7) yes
C5 . C15 . 1.406(8) yes
N6 . C7 . 1.351(7) yes
N6 . C12 . 1.481(9) yes
C7 . C8 . 1.373(9) yes
C7 . H71 . 0.927 no
C8 . C9 . 1.503(7) yes
C9 . O10 . 1.260(8) yes
C9 . O11 . 1.230(8) yes
O11 . H113 . 0.960 no
C12 . C13 . 1.457(14) yes
C12 . C14 . 1.454(11) yes
C12 . H121 . 0.984 no
C13 . C14 . 1.493(12) yes
C13 . H132 . 0.970 no
C13 . H131 . 0.978 no
C14 . H141 . 0.979 no
C14 . H142 . 0.963 no
C15 . C16 . 1.361(8) yes
C15 . H151 . 0.941 no
C16 . N17 . 1.397(7) yes
C16 . C25 . 1.429(8) yes
N17 . C18 . 1.485(8) yes
N17 . C22 . 1.458(8) yes
C18 . C19 . 1.531(10) yes
C18 . H181 . 0.952 no
C18 . H182 . 0.964 no
C19 . N20 . 1.504(8) yes
C19 . H191 . 0.966 no
C19 . H192 . 0.981 no
N20 . C21 . 1.504(8) yes
N20 . C23 . 1.490(10) yes
C21 . C22 . 1.507(10) yes
C21 . H212 . 0.964 no
C21 . H211 . 0.977 no
C22 . H221 . 0.967 no
C22 . H222 . 0.978 no
C23 . C24 . 1.517(13) yes
C23 . H232 . 0.961 no
C23 . H231 . 0.971 no
C24 . H241 . 0.961 no
C24 . H243 . 0.973 no
C24 . H242 . 0.952 no
C25 . C26 . 1.358(8) yes
C25 . F27 . 1.353(6) yes
C26 . H261 . 0.933 no
O29 . C30 . 1.247(8) yes
C30 . C31 . 1.499(7) yes
C30 . O54 . 1.255(8) yes
C31 . C32 . 1.380(8) yes
C31 . C49 . 1.434(8) yes
C32 . N33 . 1.333(7) yes
C32 . H321 . 0.925 no
N33 . C34 . 1.391(7) yes
N33 . C51 . 1.469(7) yes
C34 . C35 . 1.406(7) yes
C34 . C48 . 1.411(8) yes
C35 . C36 . 1.373(8) yes
C35 . H351 . 0.927 no
C36 . N37 . 1.390(7) yes
C36 . C45 . 1.433(8) yes
N37 . C38 . 1.455(8) yes
N37 . C42 . 1.461(8) yes
C38 . C39 . 1.510(10) yes
C38 . H381 . 0.958 no
C38 . H382 . 0.964 no
C39 . N40 . 1.499(8) yes
C39 . H391 . 0.965 no
C39 . H392 . 0.968 no
N40 . C41 . 1.495(8) yes
N40 . C43 . 1.510(10) yes
C41 . C42 . 1.528(10) yes
C41 . H411 . 0.962 no
C41 . H412 . 0.964 no
C42 . H421 . 0.963 no
C42 . H422 . 0.960 no
C43 . C44 . 1.488(14) yes
C43 . H432 . 0.974 no
C43 . H431 . 0.964 no
C44 . H441 . 0.946 no
C44 . H443 . 0.969 no
C44 . H442 . 0.970 no
C45 . F46 . 1.346(6) yes
C45 . C47 . 1.346(7) yes
C47 . C48 . 1.418(8) yes
C47 . H471 . 0.933 no
C48 . C49 . 1.451(7) yes
C49 . O50 . 1.252(7) yes
C51 . C52 . 1.499(10) yes
C51 . C53 . 1.475(10) yes
C51 . H511 . 0.972 no
C52 . C53 . 1.509(11) yes
C52 . H521 . 0.966 no
C52 . H522 . 0.958 no
C53 . H531 . 0.965 no
C53 . H532 . 0.961 no
O54 . H100 . 0.855 no
N55 . C56 . 1.361(8) yes
N55 . C72 . 1.358(9) yes
C56 . N57 . 1.348(8) yes
C56 . N69 . 1.349(9) yes
N57 . S58 . 1.584(5) yes
N57 . H571 . 0.855 no
S58 . C60 . 1.764(7) yes
S58 . O67 . 1.447(6) yes
S58 . O68 . 1.438(6) yes
C60 . C61 . 1.367(9) yes
C60 . C66 . 1.401(10) yes
C61 . C62 . 1.408(10) yes
C61 . H611 . 0.938 no
C62 . C63 . 1.393(11) yes
C62 . H621 . 0.926 no
C63 . N64 . 1.389(10) yes
C63 . C65 . 1.369(12) yes
N64 . H641 . 0.960 no
N64 . H642 . 0.948 no
C65 . C66 . 1.403(12) yes
C65 . H651 . 0.937 no
C66 . H661 . 0.936 no
N69 . C70 . 1.338(10) yes
C70 . C71 . 1.368(12) yes
C70 . H701 . 0.931 no
C71 . C72 . 1.369(11) yes
C71 . H711 . 0.938 no
C72 . H721 . 0.941 no
Cl73 . O74 . 1.397(8) yes
Cl73 . O75 . 1.399(9) yes
Cl73 . O76 . 1.380(8) yes
Cl73 . O14 . 1.422(9) 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
O2 . Zn1 . O10 . 87.19(17) yes
O2 . Zn1 . O29 . 90.43(17) yes
O10 . Zn1 . O29 . 107.6(2) yes
O2 . Zn1 . O50 . 175.29(17) yes
O10 . Zn1 . O50 . 89.07(18) yes
O29 . Zn1 . O50 . 87.98(16) yes
O2 . Zn1 . N55 . 85.40(18) yes
O10 . Zn1 . N55 . 145.0(2) yes
O29 . Zn1 . N55 . 106.6(2) yes
O50 . Zn1 . N55 . 99.31(18) yes
Zn1 . O2 . C3 . 125.0(4) yes
O2 . C3 . C4 . 119.6(5) yes
O2 . C3 . C8 . 125.5(5) yes
C4 . C3 . C8 . 114.9(5) yes
C3 . C4 . C5 . 123.6(5) yes
C3 . C4 . C26 . 119.4(5) yes
C5 . C4 . C26 . 116.9(5) yes
C4 . C5 . N6 . 117.8(5) yes
C4 . C5 . C15 . 121.3(5) yes
N6 . C5 . C15 . 120.9(5) yes
C5 . N6 . C7 . 119.9(5) yes
C5 . N6 . C12 . 120.8(5) yes
C7 . N6 . C12 . 118.9(5) yes
N6 . C7 . C8 . 124.7(5) yes
N6 . C7 . H71 . 117.7 no
C8 . C7 . H71 . 117.5 no
C3 . C8 . C7 . 119.0(5) yes
C3 . C8 . C9 . 124.7(5) yes
C7 . C8 . C9 . 116.2(5) yes
C8 . C9 . O10 . 120.0(5) yes
C8 . C9 . O11 . 116.8(6) yes
O10 . C9 . O11 . 123.2(5) yes
C9 . O10 . Zn1 . 132.7(4) yes
C9 . O11 . H113 . 109.0 no
N6 . C12 . C13 . 118.3(9) yes
N6 . C12 . C14 . 117.0(7) yes
C13 . C12 . C14 . 61.7(6) yes
N6 . C12 . H121 . 116.4 no
C13 . C12 . H121 . 114.6 no
C14 . C12 . H121 . 117.6 no
C12 . C13 . C14 . 59.1(6) yes
C12 . C13 . H132 . 120.4 no
C14 . C13 . H132 . 120.8 no
C12 . C13 . H131 . 119.2 no
C14 . C13 . H131 . 118.8 no
H132 . C13 . H131 . 110.3 no
C13 . C14 . C12 . 59.2(6) yes
C13 . C14 . H141 . 118.2 no
C12 . C14 . H141 . 121.4 no
C13 . C14 . H142 . 120.3 no
C12 . C14 . H142 . 120.6 no
H141 . C14 . H142 . 109.4 no
C5 . C15 . C16 . 121.9(6) yes
C5 . C15 . H151 . 118.6 no
C16 . C15 . H151 . 119.5 no
C15 . C16 . N17 . 124.7(5) yes
C15 . C16 . C25 . 116.1(5) yes
N17 . C16 . C25 . 119.1(5) yes
C16 . N17 . C18 . 121.0(5) yes
C16 . N17 . C22 . 119.8(5) yes
C18 . N17 . C22 . 108.6(5) yes
N17 . C18 . C19 . 110.1(5) yes
N17 . C18 . H181 . 109.5 no
C19 . C18 . H181 . 110.1 no
N17 . C18 . H182 . 110.3 no
C19 . C18 . H182 . 107.8 no
H181 . C18 . H182 . 109.0 no
C18 . C19 . N20 . 108.3(5) yes
C18 . C19 . H191 . 110.6 no
N20 . C19 . H191 . 109.3 no
C18 . C19 . H192 . 108.6 no
N20 . C19 . H192 . 110.8 no
H191 . C19 . H192 . 109.3 no
C19 . N20 . C21 . 109.5(5) yes
C19 . N20 . C23 . 113.5(6) yes
C21 . N20 . C23 . 110.4(5) yes
N20 . C21 . C22 . 110.7(5) yes
N20 . C21 . H212 . 108.3 no
C22 . C21 . H212 . 109.2 no
N20 . C21 . H211 . 108.2 no
C22 . C21 . H211 . 109.7 no
H212 . C21 . H211 . 110.8 no
C21 . C22 . N17 . 113.0(5) yes
C21 . C22 . H221 . 110.0 no
N17 . C22 . H221 . 108.0 no
C21 . C22 . H222 . 108.3 no
N17 . C22 . H222 . 108.8 no
H221 . C22 . H222 . 108.6 no
N20 . C23 . C24 . 112.8(7) yes
N20 . C23 . H232 . 108.2 no
C24 . C23 . H232 . 109.7 no
N20 . C23 . H231 . 108.1 no
C24 . C23 . H231 . 107.5 no
H232 . C23 . H231 . 110.6 no
C23 . C24 . H241 . 109.5 no
C23 . C24 . H243 . 109.2 no
H241 . C24 . H243 . 107.9 no
C23 . C24 . H242 . 111.3 no
H241 . C24 . H242 . 110.1 no
H243 . C24 . H242 . 108.8 no
C16 . C25 . C26 . 122.8(5) yes
C16 . C25 . F27 . 118.5(5) yes
C26 . C25 . F27 . 118.7(5) yes
C4 . C26 . C25 . 120.6(5) yes
C4 . C26 . H261 . 120.4 no
C25 . C26 . H261 . 119.0 no
Zn1 . O29 . C30 . 132.0(4) yes
O29 . C30 . C31 . 119.8(5) yes
O29 . C30 . O54 . 123.4(5) yes
C31 . C30 . O54 . 116.7(5) yes
C30 . C31 . C32 . 116.4(5) yes
C30 . C31 . C49 . 124.4(5) yes
C32 . C31 . C49 . 119.2(5) yes
C31 . C32 . N33 . 124.4(5) yes
C31 . C32 . H321 . 118.3 no
N33 . C32 . H321 . 117.4 no
C32 . N33 . C34 . 120.5(5) yes
C32 . N33 . C51 . 121.1(5) yes
C34 . N33 . C51 . 118.1(4) yes
N33 . C34 . C35 . 121.0(5) yes
N33 . C34 . C48 . 118.1(5) yes
C35 . C34 . C48 . 120.8(5) yes
C34 . C35 . C36 . 121.4(5) yes
C34 . C35 . H351 . 118.7 no
C36 . C35 . H351 . 119.9 no
C35 . C36 . N37 . 122.8(5) yes
C35 . C36 . C45 . 116.9(5) yes
N37 . C36 . C45 . 120.0(5) yes
C36 . N37 . C38 . 119.3(5) yes
C36 . N37 . C42 . 120.2(5) yes
C38 . N37 . C42 . 110.0(5) yes
N37 . C38 . C39 . 111.8(5) yes
N37 . C38 . H381 . 109.5 no
C39 . C38 . H381 . 109.4 no
N37 . C38 . H382 . 108.3 no
C39 . C38 . H382 . 108.2 no
H381 . C38 . H382 . 109.7 no
C38 . C39 . N40 . 111.0(5) yes
C38 . C39 . H391 . 108.2 no
N40 . C39 . H391 . 108.8 no
C38 . C39 . H392 . 110.0 no
N40 . C39 . H392 . 109.0 no
H391 . C39 . H392 . 109.8 no
C39 . N40 . C41 . 109.0(5) yes
C39 . N40 . C43 . 110.4(5) yes
C41 . N40 . C43 . 112.6(6) yes
N40 . C41 . C42 . 109.4(5) yes
N40 . C41 . H411 . 109.8 no
C42 . C41 . H411 . 109.1 no
N40 . C41 . H412 . 109.9 no
C42 . C41 . H412 . 109.0 no
H411 . C41 . H412 . 109.6 no
C41 . C42 . N37 . 111.2(5) yes
C41 . C42 . H421 . 107.0 no
N37 . C42 . H421 . 107.6 no
C41 . C42 . H422 . 111.4 no
N37 . C42 . H422 . 109.1 no
H421 . C42 . H422 . 110.4 no
N40 . C43 . C44 . 112.4(7) yes
N40 . C43 . H432 . 108.6 no
C44 . C43 . H432 . 108.5 no
N40 . C43 . H431 . 108.8 no
C44 . C43 . H431 . 108.9 no
H432 . C43 . H431 . 109.6 no
C43 . C44 . H441 . 109.3 no
C43 . C44 . H443 . 109.2 no
H441 . C44 . H443 . 110.1 no
C43 . C44 . H442 . 109.2 no
H441 . C44 . H442 . 110.3 no
H443 . C44 . H442 . 108.8 no
C36 . C45 . F46 . 118.5(5) yes
C36 . C45 . C47 . 122.8(5) yes
F46 . C45 . C47 . 118.6(5) yes
C45 . C47 . C48 . 120.6(5) yes
C45 . C47 . H471 . 119.8 no
C48 . C47 . H471 . 119.6 no
C47 . C48 . C34 . 117.4(5) yes
C47 . C48 . C49 . 120.5(5) yes
C34 . C48 . C49 . 122.1(5) yes
C48 . C49 . C31 . 115.4(5) yes
C48 . C49 . O50 . 119.0(5) yes
C31 . C49 . O50 . 125.6(5) yes
Zn1 . O50 . C49 . 125.8(3) yes
N33 . C51 . C52 . 117.8(6) yes
N33 . C51 . C53 . 119.2(6) yes
C52 . C51 . C53 . 61.0(5) yes
N33 . C51 . H511 . 116.3 no
C52 . C51 . H511 . 115.9 no
C53 . C51 . H511 . 115.3 no
C51 . C52 . C53 . 58.7(5) yes
C51 . C52 . H521 . 119.9 no
C53 . C52 . H521 . 119.1 no
C51 . C52 . H522 . 118.7 no
C53 . C52 . H522 . 119.9 no
H521 . C52 . H522 . 111.5 no
C52 . C53 . C51 . 60.3(5) yes
C52 . C53 . H531 . 119.2 no
C51 . C53 . H531 . 120.0 no
C52 . C53 . H532 . 119.1 no
C51 . C53 . H532 . 121.0 no
H531 . C53 . H532 . 109.7 no
C30 . O54 . H100 . 113.6 no
Zn1 . N55 . C56 . 120.4(4) yes
Zn1 . N55 . C72 . 121.7(5) yes
C56 . N55 . C72 . 117.8(6) yes
N55 . C56 . N57 . 114.4(6) yes
N55 . C56 . N69 . 122.6(6) yes
N57 . C56 . N69 . 123.0(6) yes
C56 . N57 . S58 . 119.1(5) yes
C56 . N57 . H571 . 96.2 no
S58 . N57 . H571 . 101.1 no
N57 . S58 . C60 . 109.5(3) yes
N57 . S58 . O67 . 105.9(3) yes
C60 . S58 . O67 . 106.2(3) yes
N57 . S58 . O68 . 112.3(3) yes
C60 . S58 . O68 . 107.7(3) yes
O67 . S58 . O68 . 114.9(4) yes
S58 . C60 . C61 . 120.3(5) yes
S58 . C60 . C66 . 119.8(6) yes
C61 . C60 . C66 . 119.8(7) yes
C60 . C61 . C62 . 120.9(6) yes
C60 . C61 . H611 . 119.2 no
C62 . C61 . H611 . 120.0 no
C61 . C62 . C63 . 119.4(7) yes
C61 . C62 . H621 . 120.0 no
C63 . C62 . H621 . 120.6 no
C62 . C63 . N64 . 119.3(7) yes
C62 . C63 . C65 . 119.7(7) yes
N64 . C63 . C65 . 120.7(8) yes
C63 . N64 . H641 . 119.8 no
C63 . N64 . H642 . 121.0 no
H641 . N64 . H642 . 119.1 no
C63 . C65 . C66 . 121.1(7) yes
C63 . C65 . H651 . 119.2 no
C66 . C65 . H651 . 119.6 no
C65 . C66 . C60 . 119.1(8) yes
C65 . C66 . H661 . 119.9 no
C60 . C66 . H661 . 121.0 no
C56 . N69 . C70 . 117.8(6) yes
N69 . C70 . C71 . 123.0(7) yes
N69 . C70 . H701 . 119.0 no
C71 . C70 . H701 . 118.0 no
C70 . C71 . C72 . 117.2(7) yes
C70 . C71 . H711 . 122.0 no
C72 . C71 . H711 . 120.8 no
C71 . C72 . N55 . 121.6(7) yes
C71 . C72 . H721 . 119.0 no
N55 . C72 . H721 . 119.4 no
O74 . Cl73 . O75 . 111.1(6) yes
O74 . Cl73 . O76 . 106.5(6) yes
O75 . Cl73 . O76 . 108.3(6) yes
O74 . Cl73 . O14 . 109.2(6) yes
O75 . Cl73 . O14 . 111.6(7) yes
O76 . Cl73 . O14 . 110.0(5) 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
C18 . H181 . O10 1_655 134.2 0.952 2.528 3.263(11) yes
C42 . H422 . O29 1_455 129.9 0.960 2.527 3.228(11) yes
C43 . H432 . O75 1_465 147.7 0.974 2.386 3.252(11) yes
C43 . H431 . O75 2_566 163.8 0.964 2.564 3.500(11) yes
C51 . H511 . O68 2_566 129.2 0.972 2.453 3.158(11) yes
O54 . H100 . N40 1_655 179.4 0.855 1.816 2.671(11) yes
N57 . H571 . O50 . 178.50 0.855 2.153 3.007(11) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 01/08/18 at 09:00:31
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
SUMFIX ELEMENT SCALES 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE O   (  11,X'S) H   ( 113,X'S) 
RIDE C   (  12,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   ( 141,X'S) H   ( 142,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  21,X'S) H   ( 212,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
RIDE C   (  23,X'S) H   ( 232,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 243,X'S) H   ( 242,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) H   ( 382,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) H   ( 392,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) H   ( 412,X'S) 
RIDE C   (  42,X'S) H   ( 421,X'S) H   ( 422,X'S) 
RIDE C   (  43,X'S) H   ( 432,X'S) H   ( 431,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) H   ( 443,X'S) H   ( 442,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) H   ( 522,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) H   ( 532,X'S) 
RIDE O   (  54,X'S) H   ( 100,X'S) 
RIDE N   (  57,X'S) H   ( 571,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) 
RIDE N   (  64,X'S) H   ( 641,X'S) H   ( 642,X'S) 
RIDE C   (  65,X'S) H   ( 651,X'S) 
RIDE C   (  66,X'S) H   ( 661,X'S) 
RIDE C   (  70,X'S) H   ( 701,X'S) 
RIDE C   (  71,X'S) H   ( 711,X'S) 
RIDE C   (  72,X'S) H   ( 721,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 01/08/18 at 09:00:31
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
U(IJ)'S  0.0, 0.001000 = CL(73) TO O(14) 
U(IJ)'S  0.0, 0.001000 = CL(73) TO O(76) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 0 3 x .
2 -1 2 x .
0 6 3 x .
-1 3 2 x .
-4 5 2 x .
5 5 5 x .
6 3 0 x .
5 3 5 x .
3 0 3 x .
0 -5 3 x .
6 5 0 x .
-2 -2 1 x .
1 7 4 x .
-3 -2 3 x .
1 3 1 x .
4 -1 4 x .
2 -2 2 x .
-3 8 11 x .
4 -2 1 x .
12 3 9 x .
0 8 3 x .
-2 -3 9 x .
-4 -1 2 x .
1 10 1 x .
-5 3 6 x .
5 4 5 x .
3 2 3 x .
4 1 1 x .
-1 -5 2 x .
-4 -4 2 x .
-4 2 7 x .
7 0 1 x .
2 7 7 x .
3 9 8 x .
-5 -4 1 x .
-2 8 4 x .
-5 -2 1 x .
6 2 0 x .
-8 -5 1 x .
-3 6 3 x .
4 2 9 x .
-2 7 6 x .
-2 5 6 x .
9 5 0 x .
-4 -3 4 x .
