# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 2190744'
loop_
_audit_author_name
_audit_author_address
'Antonios Hatzidimitriou'
;Aristotle University of Thessaloniki
Greece
;
_audit_update_record             
;
2022-07-16 deposited with the CCDC.	2022-10-18 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                   20.3724(17)
_cell_length_b                   10.6925(9)
_cell_length_c                   15.7430(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.850(2)
_cell_angle_gamma                90
_cell_volume                     3411.5(5)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c '
_symmetry_space_group_name_Hall  ?
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 0.0033 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'
Ni 0.3393 1.1124 12.8376 3.8785 7.2920 0.2565 4.4438 12.1763 2.3800 66.3421
1.0341 '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            2

# Given Formula = C60 H60 Br1 N12 Ni6 O12 
# Dc =      1.53 Fooo =   1606.00 Mu =     22.73 M =   1573.37
# Found Formula = C57 H48 Br4 N24 Ni2 O15 
# Dc =      1.70 FOOO =   1748.00 Mu =     29.77 M =   1746.20

_chemical_formula_sum            'C57 H48 Br4 N24 Ni2 O15'
_chemical_formula_moiety         'C57 H48 Br4 N24 Ni2 O15'
_chemical_compound_source        ?
_chemical_formula_weight         1746.20


_cell_measurement_reflns_used    166
_cell_measurement_theta_min      10
_cell_measurement_theta_max      20
_cell_measurement_temperature    295

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.130
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_max          0.210

_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1748
_exptl_absorpt_coefficient_mu    2.977

# Sheldrick geometric approximatio 0.66 0.68 
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  0.68
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      295
_diffrn_reflns_number            9756
_reflns_number_total             3186
_diffrn_reflns_av_R_equivalents  0.021
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3186 
# Theoretical number of reflections is about 6649 


_diffrn_reflns_theta_min         2.010
_diffrn_reflns_theta_max         25.997
_diffrn_measured_fraction_theta_max 0.950

_diffrn_reflns_theta_full        25.218
_diffrn_measured_fraction_theta_full 0.969


_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -24
_reflns_limit_h_max              24
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   2.26
_oxford_diffrn_Wilson_scale      665.87

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

_refine_diff_density_min         -0.61
_refine_diff_density_max         0.87


# 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>2.0\s(I)
_refine_ls_number_reflns         2414
_refine_ls_number_restraints     1
_refine_ls_number_parameters     234
_oxford_refine_ls_R_factor_ref   0.0376
_refine_ls_wR_factor_ref         0.0624
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_shift/su_max          0.0003651
_refine_ls_shift/su_mean         0.0000265


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3174
_refine_ls_R_factor_all          0.0584
_refine_ls_wR_factor_all         0.0659

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2414
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_gt          0.0624

# 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 Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed

# WARNING. The IUCr will not accept pure Unit Weights for F-squared refinements 
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Quasi-Unit weights 
 W = 1.0 or 1./4Fsq 
;

# 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
Ni5 Ni 0.5000 0.55048(7) 0.7500 0.0286 1.0000 Uani S T . . . .
N1 N 0.56721(15) 0.6816(3) 0.71221(17) 0.0314 1.0000 Uani . . . . . .
N2 N 0.65745(17) 0.8170(4) 0.7248(2) 0.0454 1.0000 Uani . . . . . .
N3 N 0.50282(17) 0.6652(3) 0.57996(18) 0.0360 1.0000 Uani . . . . . .
N4 N 0.47333(16) 0.5732(3) 0.62467(18) 0.0307 1.0000 Uani . . . . . .
N5 N 0.42326(15) 0.4089(3) 0.72150(18) 0.0295 1.0000 Uani . . . . . .
N6 N 0.7219(3) 0.4730(5) 0.6342(4) 0.0705 1.0000 Uani . . . . . .
O1 O 0.6897(2) 0.5353(5) 0.5856(3) 0.1108 1.0000 Uani . . . . . .
O2 O 0.7329(3) 0.5105(5) 0.7080(3) 0.1134 1.0000 Uani . . . . . .
O3 O 0.7494(2) 0.3727(6) 0.6278(3) 0.1039 1.0000 Uani . . . . . .
O4 O 0.3053(3) 0.6820(7) 0.5638(5) 0.074(2) 0.5000 Uiso . . . . . .
O5 O 0.5217(8) 0.9766(16) 0.7830(10) 0.087(6) 0.2500 Uiso D . . . 1 .
C1 C 0.6194(2) 0.7319(4) 0.7543(3) 0.0396 1.0000 Uani . . . . . .
C2 C 0.6423(2) 0.8666(4) 0.6436(3) 0.0417 1.0000 Uani . . . . . .
C3 C 0.6798(2) 0.9632(5) 0.6139(3) 0.0535 1.0000 Uani . . . . . .
C4 C 0.6607(3) 1.0137(5) 0.5350(4) 0.0653 1.0000 Uani . . . . . .
C5 C 0.6064(3) 0.9700(5) 0.4860(3) 0.0689 1.0000 Uani . . . . . .
C6 C 0.5700(3) 0.8736(5) 0.5143(3) 0.0522 1.0000 Uani . . . . . .
C7 C 0.5876(2) 0.8202(4) 0.5939(2) 0.0384 1.0000 Uani . . . . . .
C8 C 0.55083(19) 0.7198(4) 0.6275(2) 0.0328 1.0000 Uani . . . . . .
C9 C 0.4260(2) 0.5099(4) 0.5878(2) 0.0356 1.0000 Uani . . . . . .
C10 C 0.39614(19) 0.4170(4) 0.6385(2) 0.0326 1.0000 Uani . . . . . .
C11 C 0.3453(2) 0.3418(4) 0.6056(3) 0.0432 1.0000 Uani . . . . . .
C12 C 0.3198(2) 0.2553(5) 0.6569(3) 0.0473 1.0000 Uani . . . . . .
C13 C 0.3458(2) 0.2448(4) 0.7404(3) 0.0448 1.0000 Uani . . . . . .
C14 C 0.3969(2) 0.3226(4) 0.7688(2) 0.0343 1.0000 Uani . . . . . .
C15 C 0.4839(10) 1.056(2) 0.7258(12) 0.060(6) 0.2500 Uiso D . . . 1 .
Br1 Br 0.43369(2) 0.30916(5) 0.88387(3) 0.0483 1.0000 Uani . . . . . .
H11 H 0.6304 0.7041 0.8099 0.0460 1.0000 Uiso R . . . . .
H21 H 0.6881 0.8502 0.7586 0.0520 1.0000 Uiso R . . . . .
H31 H 0.7172 0.9920 0.6469 0.0609 1.0000 Uiso R . . . . .
H41 H 0.6849 1.0793 0.5147 0.0749 1.0000 Uiso R . . . . .
H42 H 0.2906 0.6678 0.5143 0.0826 0.5000 Uiso R . . . . .
H43 H 0.2789 0.7325 0.5873 0.0919 0.5000 Uiso R . . . . .
H51 H 0.5943 1.0056 0.4335 0.0780 1.0000 Uiso R . . . . .
H52 H 0.5493 0.9311 0.7606 0.0900 0.2500 Uiso R . . . 1 .
H61 H 0.5335 0.8435 0.4806 0.0588 1.0000 Uiso R . . . . .
H91 H 0.4114 0.5226 0.5306 0.0411 1.0000 Uiso R . . . . .
H111 H 0.3287 0.3495 0.5490 0.0509 1.0000 Uiso R . . . . .
H121 H 0.2853 0.2034 0.6354 0.0538 1.0000 Uiso R . . . . .
H131 H 0.3292 0.1866 0.7762 0.0501 1.0000 Uiso R . . . . .
H151 H 0.4544 1.1031 0.7560 0.0730 0.2500 Uiso R . . . 1 .
H152 H 0.4593 1.0063 0.6835 0.0730 0.2500 Uiso R . . . 1 .
H153 H 0.5123 1.1104 0.6992 0.0730 0.2500 Uiso R . . . 1 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.043256(4)
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
Ni5 . N5 6_656 2.189(3) yes
Ni5 . N1 6_656 2.088(3) yes
Ni5 . N4 6_656 2.007(3) yes
Ni5 . N1 . 2.088(3) yes
Ni5 . N4 . 2.007(3) yes
Ni5 . N5 . 2.189(3) yes
N1 . C1 . 1.310(5) yes
N1 . C8 . 1.402(5) yes
N2 . C1 . 1.311(5) yes
N2 . C2 . 1.389(5) yes
N2 . H21 . 0.855 no
N3 . N4 . 1.382(4) yes
N3 . C8 . 1.307(5) yes
N4 . C9 . 1.269(5) yes
N5 . C10 . 1.368(4) yes
N5 . C14 . 1.333(5) yes
N6 . O1 . 1.165(6) yes
N6 . O2 . 1.229(6) yes
N6 . O3 . 1.219(6) yes
O4 . H42 . 0.820 no
O4 . H43 . 0.871 no
O5 . C15 . 1.405(5) yes
O5 . H52 . 0.848 no
C1 . H11 . 0.930 no
C2 . C3 . 1.394(6) yes
C2 . C7 . 1.387(6) yes
C3 . C4 . 1.374(7) yes
C3 . H31 . 0.930 no
C4 . C5 . 1.366(7) yes
C4 . H41 . 0.932 no
C5 . C6 . 1.371(6) yes
C5 . H51 . 0.921 no
C6 . C7 . 1.389(6) yes
C6 . H61 . 0.926 no
C7 . C8 . 1.440(6) yes
C9 . C10 . 1.447(5) yes
C9 . H91 . 0.930 no
C10 . C11 . 1.371(5) yes
C11 . C12 . 1.365(6) yes
C11 . H111 . 0.924 no
C12 . C13 . 1.371(6) yes
C12 . H121 . 0.931 no
C13 . C14 . 1.371(6) yes
C13 . H131 . 0.927 no
C14 . Br1 . 1.894(4) yes
C15 . H151 . 0.950 no
C15 . H152 . 0.950 no
C15 . H153 . 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
N5 6_656 Ni5 . N1 6_656 151.77(11) yes
N5 6_656 Ni5 . N4 6_656 76.47(12) yes
N1 6_656 Ni5 . N4 6_656 76.02(12) yes
N5 6_656 Ni5 . N1 . 92.72(12) yes
N1 6_656 Ni5 . N1 . 95.64(18) yes
N4 6_656 Ni5 . N1 . 94.55(12) yes
N5 6_656 Ni5 . N4 . 113.65(12) yes
N1 6_656 Ni5 . N4 . 94.55(12) yes
N4 6_656 Ni5 . N4 . 166.1(2) yes
N1 . Ni5 . N4 . 76.02(12) yes
N5 6_656 Ni5 . N5 . 92.53(17) yes
N1 6_656 Ni5 . N5 . 92.72(12) yes
N4 6_656 Ni5 . N5 . 113.65(12) yes
N1 . Ni5 . N5 . 151.77(11) yes
N4 . Ni5 . N5 . 76.47(12) yes
Ni5 . N1 . C1 . 130.8(3) yes
Ni5 . N1 . C8 . 111.5(2) yes
C1 . N1 . C8 . 117.7(4) yes
C1 . N2 . C2 . 120.5(4) yes
C1 . N2 . H21 . 119.1 no
C2 . N2 . H21 . 119.7 no
N4 . N3 . C8 . 111.4(3) yes
N3 . N4 . Ni5 . 119.9(2) yes
N3 . N4 . C9 . 119.7(3) yes
Ni5 . N4 . C9 . 120.1(3) yes
Ni5 . N5 . C10 . 111.2(3) yes
Ni5 . N5 . C14 . 133.2(3) yes
C10 . N5 . C14 . 115.5(3) yes
O1 . N6 . O2 . 118.1(7) yes
O1 . N6 . O3 . 133.0(7) yes
O2 . N6 . O3 . 108.9(6) yes
H42 . O4 . H43 . 109.7 no
C15 . O5 . H52 . 115.0 no
N2 . C1 . N1 . 125.7(4) yes
N2 . C1 . H11 . 117.5 no
N1 . C1 . H11 . 116.8 no
N2 . C2 . C3 . 120.9(4) yes
N2 . C2 . C7 . 118.3(4) yes
C3 . C2 . C7 . 120.8(4) yes
C2 . C3 . C4 . 118.7(5) yes
C2 . C3 . H31 . 120.3 no
C4 . C3 . H31 . 121.0 no
C3 . C4 . C5 . 121.0(5) yes
C3 . C4 . H41 . 119.7 no
C5 . C4 . H41 . 119.3 no
C4 . C5 . C6 . 120.5(5) yes
C4 . C5 . H51 . 119.5 no
C6 . C5 . H51 . 120.0 no
C5 . C6 . C7 . 120.3(5) yes
C5 . C6 . H61 . 120.3 no
C7 . C6 . H61 . 119.5 no
C6 . C7 . C2 . 118.7(4) yes
C6 . C7 . C8 . 122.8(4) yes
C2 . C7 . C8 . 118.5(4) yes
C7 . C8 . N1 . 119.0(3) yes
C7 . C8 . N3 . 120.6(3) yes
N1 . C8 . N3 . 120.4(4) yes
N4 . C9 . C10 . 117.2(3) yes
N4 . C9 . H91 . 121.3 no
C10 . C9 . H91 . 121.6 no
C9 . C10 . N5 . 114.8(3) yes
C9 . C10 . C11 . 122.6(3) yes
N5 . C10 . C11 . 122.7(4) yes
C10 . C11 . C12 . 119.5(4) yes
C10 . C11 . H111 . 120.1 no
C12 . C11 . H111 . 120.4 no
C11 . C12 . C13 . 119.3(4) yes
C11 . C12 . H121 . 120.5 no
C13 . C12 . H121 . 120.2 no
C12 . C13 . C14 . 118.0(4) yes
C12 . C13 . H131 . 120.6 no
C14 . C13 . H131 . 121.4 no
C13 . C14 . N5 . 125.0(4) yes
C13 . C14 . Br1 . 118.6(3) yes
N5 . C14 . Br1 . 116.4(3) yes
O5 . C15 . H151 . 109.5 no
O5 . C15 . H152 . 109.4 no
H151 . C15 . H152 . 109.5 no
O5 . C15 . H153 . 109.6 no
H151 . C15 . H153 . 109.5 no
H152 . C15 . H153 . 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
C1 . H11 . O4 6_656 156 0.93 2.28 3.153(8) yes
N2 . H21 . O2 8_656 151 0.86 2.37 3.147(8) yes
N2 . H21 . O3 8_656 157 0.86 2.10 2.906(8) yes
C3 . H31 . O2 8_656 143 0.93 2.41 3.203(8) yes
O4 . H42 . O3 2_666 179 0.82 2.34 3.162(8) yes
O4 . H43 . O3 3_455 159 0.87 1.76 2.589(8) yes
O5 . H52 . C1 . 152 0.85 2.57 3.347(8) yes
C11 . H111 . O1 2_666 153 0.92 2.45 3.295(8) yes


# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2190745'
loop_
_audit_author_name
_audit_author_address
'Antonios Hatzidimitriou'
;Aristotle University of Thessaloniki
Greece
;
_audit_update_record             
;
2022-07-16 deposited with the CCDC.	2022-10-18 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                   7.802(4)
_cell_length_b                   14.426(9)
_cell_length_c                   13.723(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.399(15)
_cell_angle_gamma                90
_cell_volume                     1539.9(15)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  ?
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'
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'
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'
Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C10 H10 Cl1 Cu1 F1 N2 O2 
# Dc =      1.33 Fooo =    620.00 Mu =     15.94 M =    308.20
# Found Formula = C14 H10 Cl2 Cu1 F1 N5 
# Dc =      1.73 FOOO =    804.00 Mu =     17.80 M =    401.72

_chemical_formula_sum            'C14 H10 Cl2 Cu1 F1 N5'
_chemical_formula_moiety         'C14 H10 Cl2 Cu1 F1 N5'
_chemical_compound_source        ?
_chemical_formula_weight         401.72


_cell_measurement_reflns_used    172
_cell_measurement_theta_min      10
_cell_measurement_theta_max      20
_cell_measurement_temperature    295

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.160
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_max          0.220

_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             804
_exptl_absorpt_coefficient_mu    1.780

# Sheldrick geometric approximatio 0.74 0.75 
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.75
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      295
_diffrn_reflns_number            10474
_reflns_number_total             2913
_diffrn_reflns_av_R_equivalents  0.058
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2913 
# Theoretical number of reflections is about 5937 


_diffrn_reflns_theta_min         2.051
_diffrn_reflns_theta_max         25.818
_diffrn_measured_fraction_theta_max 0.980

_diffrn_reflns_theta_full        25.044
_diffrn_measured_fraction_theta_full 0.988


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   2.52
_oxford_diffrn_Wilson_scale      67.22

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

_refine_diff_density_min         -0.45
_refine_diff_density_max         0.54


# 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>2.0\s(I)
_refine_ls_number_reflns         2158
_refine_ls_number_restraints     0
_refine_ls_number_parameters     208
_oxford_refine_ls_R_factor_ref   0.0455
_refine_ls_wR_factor_ref         0.0772
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_shift/su_max          0.0002440
_refine_ls_shift/su_mean         0.0000256


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2903
_refine_ls_R_factor_all          0.0767
_refine_ls_wR_factor_all         0.0912

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2158
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_gt          0.0772

# 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 Fsqd
_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: 
 2.29 2.67 0.888 
;

# 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
Cu1 Cu 0.49851(7) 0.70947(4) 0.36860(4) 0.0338 1.0000 Uani . . . . . .
Cl1 Cl 0.75511(16) 0.81303(8) 0.33760(9) 0.0477 1.0000 Uani . . . . . .
Cl2 Cl 0.37493(16) 0.69191(8) 0.21735(8) 0.0454 1.0000 Uani . . . . . .
N1 N 0.6151(4) 0.5872(2) 0.3822(2) 0.0297 1.0000 Uani . . . . . .
N2 N 0.7339(5) 0.4514(2) 0.3272(3) 0.0355 1.0000 Uani . . . . . .
N3 N 0.6327(4) 0.6224(2) 0.5498(2) 0.0298 1.0000 Uani . . . . . .
N4 N 0.5455(4) 0.6980(2) 0.5104(2) 0.0306 1.0000 Uani . . . . . .
N5 N 0.3718(5) 0.8233(3) 0.4148(3) 0.0381 1.0000 Uani . . . . . .
C1 C 0.6486(6) 0.5290(3) 0.3123(3) 0.0351 1.0000 Uani . . . . . .
C2 C 0.7969(5) 0.4252(3) 0.4204(3) 0.0326 1.0000 Uani . . . . . .
C3 C 0.8923(6) 0.3432(3) 0.4333(4) 0.0414 1.0000 Uani . . . . . .
C4 C 0.9500(6) 0.3195(3) 0.5254(4) 0.0470 1.0000 Uani . . . . . .
C5 C 0.9195(6) 0.3739(4) 0.6053(4) 0.0453 1.0000 Uani . . . . . .
C6 C 0.8243(6) 0.4547(3) 0.5920(3) 0.0342 1.0000 Uani . . . . . .
C7 C 0.7639(5) 0.4819(3) 0.4987(3) 0.0291 1.0000 Uani . . . . . .
C8 C 0.6685(5) 0.5660(3) 0.4778(3) 0.0256 1.0000 Uani . . . . . .
C9 C 0.4924(6) 0.7620(3) 0.5642(3) 0.0383 1.0000 Uani . . . . . .
C10 C 0.3984(6) 0.8360(3) 0.5119(4) 0.0387 1.0000 Uani . . . . . .
C11 C 0.3412(7) 0.9158(3) 0.5538(4) 0.0497 1.0000 Uani . . . . . .
C12 C 0.2584(8) 0.9825(4) 0.4992(5) 0.0642 1.0000 Uani . . . . . .
C13 C 0.2320(8) 0.9684(4) 0.4016(5) 0.0677 1.0000 Uani . . . . . .
C14 C 0.2901(7) 0.8880(4) 0.3608(4) 0.0540 1.0000 Uani . . . . . .
F1 F 0.3751(5) 0.9263(2) 0.6505(3) 0.0725 1.0000 Uani . . . . . .
H11 H 0.6102 0.5442 0.2481 0.0422 1.0000 Uiso R . . . . .
H21 H 0.7480 0.4156 0.2780 0.0430 1.0000 Uiso R . . . . .
H31 H 0.9135 0.3064 0.3802 0.0500 1.0000 Uiso R . . . . .
H41 H 1.0136 0.2659 0.5356 0.0569 1.0000 Uiso R . . . . .
H51 H 0.9619 0.3561 0.6677 0.0548 1.0000 Uiso R . . . . .
H61 H 0.8005 0.4906 0.6452 0.0421 1.0000 Uiso R . . . . .
H91 H 0.5122 0.7612 0.6313 0.0461 1.0000 Uiso R . . . . .
H121 H 0.2223 1.0366 0.5280 0.0789 1.0000 Uiso R . . . . .
H131 H 0.1760 1.0127 0.3619 0.0839 1.0000 Uiso R . . . . .
H141 H 0.2724 0.8788 0.2938 0.0641 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.11824(4)
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
Cu1 . Cl1 . 2.5595(16) yes
Cu1 . Cl2 . 2.2349(17) yes
Cu1 . N1 . 1.986(4) yes
Cu1 . N4 . 1.959(4) yes
Cu1 . N5 . 2.043(4) yes
N1 . C1 . 1.315(5) yes
N1 . C8 . 1.380(5) yes
N2 . C1 . 1.310(6) yes
N2 . C2 . 1.387(6) yes
N2 . H21 . 0.863 no
N3 . N4 . 1.374(5) yes
N3 . C8 . 1.326(5) yes
N4 . C9 . 1.271(5) yes
N5 . C10 . 1.346(6) yes
N5 . C14 . 1.324(6) yes
C1 . H11 . 0.935 no
C2 . C3 . 1.402(6) yes
C2 . C7 . 1.390(6) yes
C3 . C4 . 1.352(7) yes
C3 . H31 . 0.925 no
C4 . C5 . 1.384(7) yes
C4 . H41 . 0.924 no
C5 . C6 . 1.387(6) yes
C5 . H51 . 0.930 no
C6 . C7 . 1.386(6) yes
C6 . H61 . 0.925 no
C7 . C8 . 1.442(6) yes
C9 . C10 . 1.454(6) yes
C9 . H91 . 0.922 no
C10 . C11 . 1.376(6) yes
C11 . C12 . 1.354(8) yes
C11 . F1 . 1.341(6) yes
C12 . C13 . 1.354(9) yes
C12 . H121 . 0.928 no
C13 . C14 . 1.379(8) yes
C13 . H131 . 0.928 no
C14 . H141 . 0.930 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
Cl1 . Cu1 . Cl2 . 101.48(5) yes
Cl1 . Cu1 . N1 . 100.10(12) yes
Cl2 . Cu1 . N1 . 98.53(11) yes
Cl1 . Cu1 . N4 . 97.19(11) yes
Cl2 . Cu1 . N4 . 161.32(11) yes
N1 . Cu1 . N4 . 77.42(14) yes
Cl1 . Cu1 . N5 . 89.18(12) yes
Cl2 . Cu1 . N5 . 101.22(12) yes
N1 . Cu1 . N5 . 156.04(15) yes
N4 . Cu1 . N5 . 79.53(15) yes
Cu1 . N1 . C1 . 127.9(3) yes
Cu1 . N1 . C8 . 112.9(3) yes
C1 . N1 . C8 . 119.3(4) yes
C1 . N2 . C2 . 121.1(4) yes
C1 . N2 . H21 . 118.9 no
C2 . N2 . H21 . 120.0 no
N4 . N3 . C8 . 108.6(3) yes
N3 . N4 . Cu1 . 120.5(2) yes
N3 . N4 . C9 . 121.4(4) yes
Cu1 . N4 . C9 . 118.1(3) yes
Cu1 . N5 . C10 . 112.0(3) yes
Cu1 . N5 . C14 . 128.1(4) yes
C10 . N5 . C14 . 119.2(4) yes
N1 . C1 . N2 . 124.0(4) yes
N1 . C1 . H11 . 118.0 no
N2 . C1 . H11 . 118.0 no
N2 . C2 . C3 . 119.6(4) yes
N2 . C2 . C7 . 118.6(4) yes
C3 . C2 . C7 . 121.8(4) yes
C2 . C3 . C4 . 117.8(4) yes
C2 . C3 . H31 . 120.6 no
C4 . C3 . H31 . 121.6 no
C3 . C4 . C5 . 122.2(5) yes
C3 . C4 . H41 . 119.3 no
C5 . C4 . H41 . 118.5 no
C4 . C5 . C6 . 119.7(4) yes
C4 . C5 . H51 . 120.2 no
C6 . C5 . H51 . 120.1 no
C5 . C6 . C7 . 120.0(4) yes
C5 . C6 . H61 . 120.3 no
C7 . C6 . H61 . 119.8 no
C2 . C7 . C6 . 118.6(4) yes
C2 . C7 . C8 . 117.7(4) yes
C6 . C7 . C8 . 123.8(4) yes
C7 . C8 . N1 . 119.3(4) yes
C7 . C8 . N3 . 120.2(4) yes
N1 . C8 . N3 . 120.5(4) yes
N4 . C9 . C10 . 114.9(4) yes
N4 . C9 . H91 . 122.3 no
C10 . C9 . H91 . 122.8 no
C9 . C10 . N5 . 115.0(4) yes
C9 . C10 . C11 . 125.1(5) yes
N5 . C10 . C11 . 119.9(5) yes
C10 . C11 . C12 . 121.3(6) yes
C10 . C11 . F1 . 117.5(5) yes
C12 . C11 . F1 . 121.1(5) yes
C11 . C12 . C13 . 118.1(5) yes
C11 . C12 . H121 . 120.6 no
C13 . C12 . H121 . 121.3 no
C12 . C13 . C14 . 119.9(5) yes
C12 . C13 . H131 . 120.5 no
C14 . C13 . H131 . 119.7 no
C13 . C14 . N5 . 121.7(6) yes
C13 . C14 . H141 . 119.6 no
N5 . C14 . H141 . 118.7 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_I_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2190748'
loop_
_audit_author_name
_audit_author_address
'Antonios Hatzidimitriou'
;Aristotle University of Thessaloniki
Greece
;
_audit_update_record             
;
2022-07-16 deposited with the CCDC.	2022-10-18 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                   10.3840(5)
_cell_length_b                   27.3190(15)
_cell_length_c                   12.0585(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.9964(19)
_cell_angle_gamma                90
_cell_volume                     3346.1(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  ?
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'
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'
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            2

# Given Formula = C60 H60 F6 N12 O12 P6 Zn6 
# Dc =      1.82 Fooo =   1848.00 Mu =     23.48 M =   1833.32
# Found Formula = C57 H44 F16 N22 O7 P2 Zn2 
# Dc =      1.63 FOOO =   1660.00 Mu =      8.79 M =   1645.80

_chemical_formula_sum            'C57 H44 F16 N22 O7 P2 Zn2'
_chemical_formula_moiety         'C57 H44 F16 N22 O7 P2 Zn2'
_chemical_compound_source        ?
_chemical_formula_weight         1645.80


_cell_measurement_reflns_used    299
_cell_measurement_theta_min      10
_cell_measurement_theta_max      20
_cell_measurement_temperature    295

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.160
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_max          0.230

_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1660
_exptl_absorpt_coefficient_mu    0.879

# Sheldrick geometric approximatio 0.82 0.87 
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.87
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      295
_diffrn_reflns_number            34148
_reflns_number_total             6355
_diffrn_reflns_av_R_equivalents  0.015
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 6355 
# Theoretical number of reflections is about 12802 


_diffrn_reflns_theta_min         1.491
_diffrn_reflns_theta_max         25.748
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        25.233
_diffrn_measured_fraction_theta_full 0.994


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              33
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   3.43
_oxford_diffrn_Wilson_scale      317.89

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

_refine_diff_density_min         -0.40
_refine_diff_density_max         0.58


# 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>2.0\s(I)
_refine_ls_number_reflns         4859
_refine_ls_number_restraints     1
_refine_ls_number_parameters     471
_oxford_refine_ls_R_factor_ref   0.0419
_refine_ls_wR_factor_ref         0.0850
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_shift/su_max          0.0005558
_refine_ls_shift/su_mean         0.0000570


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        6335
_refine_ls_R_factor_all          0.0575
_refine_ls_wR_factor_all         0.0884

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4859
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_gt          0.0850

# 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 Fsqd
_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: 
 1.90 2.42 0.648 
;

# 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 0.99657(3) 0.610128(12) 0.38352(3) 0.0415 1.0000 Uani . . . . . .
N1 N 0.9389(2) 0.55300(9) 0.2620(2) 0.0449 1.0000 Uani . . . . . .
N2 N 0.8338(3) 0.51723(11) 0.0910(3) 0.0651 1.0000 Uani . . . . . .
N3 N 1.0939(2) 0.50627(8) 0.3893(2) 0.0436 1.0000 Uani . . . . . .
N4 N 1.0969(2) 0.54832(8) 0.4536(2) 0.0400 1.0000 Uani . . . . . .
N5 N 1.1090(2) 0.63318(9) 0.5578(2) 0.0414 1.0000 Uani . . . . . .
N6 N 0.8116(2) 0.62451(8) 0.4280(2) 0.0388 1.0000 Uani . . . . . .
N7 N 0.6314(3) 0.60800(10) 0.5091(3) 0.0597 1.0000 Uani . . . . . .
N8 N 0.8413(2) 0.70479(8) 0.3648(2) 0.0394 1.0000 Uani . . . . . .
N9 N 0.9499(2) 0.68276(8) 0.33760(19) 0.0383 1.0000 Uani . . . . . .
N10 N 1.1596(2) 0.63640(10) 0.3009(2) 0.0462 1.0000 Uani . . . . . .
N11 N 0.4979(4) 0.48408(18) 0.3653(4) 0.0888 1.0000 Uani . . . . . .
O1 O 0.5582(4) 0.52140(14) 0.3351(4) 0.1191 1.0000 Uani . . . . . .
O2 O 0.3894(5) 0.4756(2) 0.3218(4) 0.1534 1.0000 Uani . . . . . .
O3 O 0.5541(4) 0.45836(16) 0.4421(4) 0.1313 1.0000 Uani . . . . . .
O4 O 0.3431(6) 0.4944(2) 0.1039(6) 0.0960(19) 0.5000 Uiso D . . . . .
C1 C 0.8553(3) 0.55323(13) 0.1665(3) 0.0595 1.0000 Uani . . . . . .
C2 C 0.9100(3) 0.47540(12) 0.1100(3) 0.0539 1.0000 Uani . . . . . .
C3 C 0.8925(4) 0.43768(17) 0.0279(4) 0.0776 1.0000 Uani . . . . . .
C4 C 0.9711(5) 0.39730(16) 0.0497(4) 0.0890 1.0000 Uani . . . . . .
C5 C 1.0639(5) 0.39272(16) 0.1453(4) 0.0874 1.0000 Uani . . . . . .
C6 C 1.0806(4) 0.42937(13) 0.2264(4) 0.0700 1.0000 Uani . . . . . .
C7 C 1.0015(3) 0.47125(11) 0.2089(3) 0.0473 1.0000 Uani . . . . . .
C8 C 1.0145(3) 0.51091(10) 0.2916(3) 0.0402 1.0000 Uani . . . . . .
C9 C 1.1711(3) 0.54833(11) 0.5538(3) 0.0451 1.0000 Uani . . . . . .
C10 C 1.1777(3) 0.59562(11) 0.6137(2) 0.0416 1.0000 Uani . . . . . .
C11 C 1.2538(3) 0.60299(14) 0.7199(3) 0.0571 1.0000 Uani . . . . . .
C12 C 1.2657(4) 0.64878(17) 0.7688(3) 0.0692 1.0000 Uani . . . . . .
C13 C 1.1979(4) 0.68668(15) 0.7099(3) 0.0670 1.0000 Uani . . . . . .
C14 C 1.1189(3) 0.67703(12) 0.6053(3) 0.0531 1.0000 Uani . . . . . .
C15 C 0.7388(3) 0.59510(11) 0.4749(3) 0.0494 1.0000 Uani . . . . . .
C16 C 0.5857(3) 0.65537(11) 0.4976(3) 0.0471 1.0000 Uani . . . . . .
C17 C 0.4712(3) 0.66908(14) 0.5340(3) 0.0648 1.0000 Uani . . . . . .
C18 C 0.4289(4) 0.71668(15) 0.5209(4) 0.0693 1.0000 Uani . . . . . .
C19 C 0.4989(4) 0.75073(13) 0.4740(3) 0.0643 1.0000 Uani . . . . . .
C20 C 0.6117(3) 0.73745(12) 0.4385(3) 0.0547 1.0000 Uani . . . . . .
C21 C 0.6564(3) 0.68935(10) 0.4486(2) 0.0396 1.0000 Uani . . . . . .
C22 C 0.7743(3) 0.67301(9) 0.4119(2) 0.0347 1.0000 Uani . . . . . .
C23 C 1.0308(3) 0.70907(11) 0.2972(2) 0.0442 1.0000 Uani . . . . . .
C24 C 1.1463(3) 0.68447(12) 0.2742(2) 0.0468 1.0000 Uani . . . . . .
C25 C 1.2427(4) 0.70791(15) 0.2305(3) 0.0627 1.0000 Uani . . . . . .
C26 C 1.3507(4) 0.68298(19) 0.2107(4) 0.0785 1.0000 Uani . . . . . .
C27 C 1.3615(4) 0.63400(19) 0.2370(4) 0.0779 1.0000 Uani . . . . . .
C28 C 1.2642(3) 0.61216(15) 0.2821(3) 0.0639 1.0000 Uani . . . . . .
C29 C 0.4565(10) 0.5125(5) 0.0700(12) 0.134(4) 0.5000 Uiso D . . . . .
H11 H 0.8045 0.5807 0.1504 0.0708 1.0000 Uiso R . . . . .
H21 H 0.7808 0.5217 0.0283 0.0782 1.0000 Uiso R . . . . .
H31 H 0.8298 0.4406 -0.0373 0.0933 1.0000 Uiso R . . . . .
H41 H 0.9594 0.3728 -0.0037 0.1071 1.0000 Uiso R . . . . .
H51 H 1.1154 0.3650 0.1570 0.1046 1.0000 Uiso R . . . . .
H61 H 1.1444 0.4264 0.2921 0.0839 1.0000 Uiso R . . . . .
H71 H 0.5866 0.5864 0.5326 0.0721 1.0000 Uiso R . . . . .
H91 H 1.2295 0.5200 0.5876 0.0512 1.0000 Uiso R . . . . .
H121 H 1.3198 0.6534 0.8393 0.0822 1.0000 Uiso R . . . . .
H131 H 1.2062 0.7179 0.7398 0.0800 1.0000 Uiso R . . . . .
H141 H 1.0700 0.7016 0.5660 0.0638 1.0000 Uiso R . . . . .
H151 H 0.7648 0.5628 0.4873 0.0589 1.0000 Uiso R . . . . .
H171 H 0.4242 0.6459 0.5653 0.0780 1.0000 Uiso R . . . . .
H181 H 0.3544 0.7262 0.5438 0.0828 1.0000 Uiso R . . . . .
H191 H 0.4703 0.7827 0.4676 0.0766 1.0000 Uiso R . . . . .
H201 H 0.6580 0.7607 0.4076 0.0650 1.0000 Uiso R . . . . .
H231 H 1.0172 0.7417 0.2840 0.0531 1.0000 Uiso R . . . . .
H261 H 1.4141 0.6983 0.1808 0.0941 1.0000 Uiso R . . . . .
H271 H 1.4318 0.6158 0.2233 0.0928 1.0000 Uiso R . . . . .
H281 H 1.2716 0.5787 0.2996 0.0753 1.0000 Uiso R . . . . .
H291 H 0.5102 0.4853 0.0614 0.2020 0.5000 Uiso R . . . . .
H292 H 0.5000 0.5342 0.1285 0.2020 0.5000 Uiso R . . . . .
H293 H 0.4295 0.5294 0.0005 0.2023 0.5000 Uiso R . . . . .
H294 H 0.3577 0.4884 0.1729 0.1151 0.5000 Uiso R . . . . .
F1 F 1.3184(2) 0.56462(10) 0.77547(18) 0.0842 1.0000 Uani . . . . . .
F2 F 1.2306(2) 0.75642(9) 0.2096(2) 0.0857 1.0000 Uani . . . . . .
F3 F 0.3629(7) 0.3024(3) -0.1321(7) 0.123(2) 0.5000 Uiso . . . . 1 .
F4 F 0.4027(6) 0.3435(2) 0.1174(5) 0.1126(19) 0.5000 Uiso . . . . 1 .
F5 F 0.5049(5) 0.3049(2) 0.0086(5) 0.0916(15) 0.5000 Uiso . . . . 1 .
F6 F 0.2215(6) 0.3472(3) -0.0246(6) 0.1043(19) 0.5000 Uiso . . . . 1 .
F7 F 0.4139(7) 0.3763(3) -0.0604(6) 0.125(2) 0.5000 Uiso . . . . 1 .
F8 F 0.3248(6) 0.2781(2) 0.0333(6) 0.1052(18) 0.5000 Uiso . . . . 1 .
F9 F 0.3453(5) 0.3848(2) 0.0281(5) 0.0939(15) 0.5000 Uiso . . . . 2 .
F10 F 0.3567(8) 0.2819(3) -0.0836(7) 0.130(3) 0.5000 Uiso . . . . 2 .
F11 F 0.3383(7) 0.3068(3) 0.0862(7) 0.126(2) 0.5000 Uiso . . . . 2 .
F12 F 0.3623(4) 0.35788(16) -0.1442(4) 0.0656(10) 0.5000 Uiso . . . . 2 .
F13 F 0.5183(6) 0.3388(2) 0.0015(5) 0.1004(17) 0.5000 Uiso . . . . 2 .
F14 F 0.2038(5) 0.3309(2) -0.0744(5) 0.0853(15) 0.5000 Uiso . . . . 2 .
P1 P 0.36497(11) 0.33150(4) -0.01867(11) 0.0729 1.0000 Uani . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.079824(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
Zn1 . N1 . 2.139(2) yes
Zn1 . N4 . 2.070(2) yes
Zn1 . N5 . 2.271(2) yes
Zn1 . N6 . 2.135(2) yes
Zn1 . N9 . 2.090(2) yes
Zn1 . N10 . 2.253(2) yes
N1 . C1 . 1.290(4) yes
N1 . C8 . 1.396(4) yes
N2 . C1 . 1.327(4) yes
N2 . C2 . 1.382(4) yes
N2 . H21 . 0.846 no
N3 . N4 . 1.383(3) yes
N3 . C8 . 1.296(4) yes
N4 . C9 . 1.291(4) yes
N5 . C10 . 1.348(4) yes
N5 . C14 . 1.322(4) yes
N6 . C15 . 1.310(4) yes
N6 . C22 . 1.383(3) yes
N7 . C15 . 1.315(4) yes
N7 . C16 . 1.375(4) yes
N7 . H71 . 0.836 no
N8 . N9 . 1.376(3) yes
N8 . C22 . 1.313(3) yes
N9 . C23 . 1.277(4) yes
N10 . C24 . 1.352(4) yes
N10 . C28 . 1.331(4) yes
N11 . O1 . 1.288(5) yes
N11 . O2 . 1.163(5) yes
N11 . O3 . 1.211(5) yes
O4 . C29 . 1.415(5) yes
O4 . H294 . 0.830 no
C1 . H11 . 0.914 no
C2 . C3 . 1.414(5) yes
C2 . C7 . 1.367(5) yes
C3 . C4 . 1.365(6) yes
C3 . H31 . 0.914 no
C4 . C5 . 1.346(7) yes
C4 . H41 . 0.920 no
C5 . C6 . 1.385(5) yes
C5 . H51 . 0.920 no
C6 . C7 . 1.398(5) yes
C6 . H61 . 0.925 no
C7 . C8 . 1.459(4) yes
C9 . C10 . 1.475(4) yes
C9 . H91 . 1.014 no
C10 . C11 . 1.373(4) yes
C11 . C12 . 1.377(5) yes
C11 . F1 . 1.346(4) yes
C12 . C13 . 1.365(6) yes
C12 . H121 . 0.925 no
C13 . C14 . 1.380(5) yes
C13 . H131 . 0.922 no
C14 . H141 . 0.912 no
C15 . H151 . 0.925 no
C16 . C17 . 1.400(4) yes
C16 . C21 . 1.389(4) yes
C17 . C18 . 1.371(5) yes
C17 . H171 . 0.926 no
C18 . C19 . 1.372(5) yes
C18 . H181 . 0.911 no
C19 . C20 . 1.377(5) yes
C19 . H191 . 0.920 no
C20 . C21 . 1.391(4) yes
C20 . H201 . 0.921 no
C21 . C22 . 1.455(4) yes
C23 . C24 . 1.451(4) yes
C23 . H231 . 0.911 no
C24 . C25 . 1.382(4) yes
C25 . C26 . 1.375(6) yes
C25 . F2 . 1.350(5) yes
C26 . C27 . 1.374(6) yes
C26 . H261 . 0.916 no
C27 . C28 . 1.379(5) yes
C27 . H271 . 0.926 no
C28 . H281 . 0.938 no
C29 . H291 . 0.948 no
C29 . H292 . 0.959 no
C29 . H293 . 0.947 no
F3 . P1 . 1.578(8) yes
F4 . P1 . 1.639(7) yes
F5 . P1 . 1.596(6) yes
F6 . P1 . 1.537(7) yes
F7 . P1 . 1.454(7) yes
F8 . P1 . 1.674(6) yes
F9 . P1 . 1.589(6) yes
F10 . P1 . 1.559(8) yes
F11 . P1 . 1.508(7) yes
F12 . P1 . 1.671(4) yes
F13 . P1 . 1.573(6) yes
F14 . P1 . 1.668(6) 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
N1 . Zn1 . N4 . 74.35(9) yes
N1 . Zn1 . N5 . 148.55(9) yes
N4 . Zn1 . N5 . 74.33(9) yes
N1 . Zn1 . N6 . 99.64(9) yes
N4 . Zn1 . N6 . 116.75(9) yes
N5 . Zn1 . N6 . 91.88(9) yes
N1 . Zn1 . N9 . 119.65(9) yes
N4 . Zn1 . N9 . 162.19(9) yes
N5 . Zn1 . N9 . 91.62(9) yes
N6 . Zn1 . N9 . 73.77(9) yes
N1 . Zn1 . N10 . 93.38(9) yes
N4 . Zn1 . N10 . 94.58(10) yes
N5 . Zn1 . N10 . 91.83(9) yes
N6 . Zn1 . N10 . 148.25(9) yes
N9 . Zn1 . N10 . 74.62(9) yes
Zn1 . N1 . C1 . 130.4(2) yes
Zn1 . N1 . C8 . 111.30(19) yes
C1 . N1 . C8 . 118.0(3) yes
C1 . N2 . C2 . 119.4(3) yes
C1 . N2 . H21 . 119.4 no
C2 . N2 . H21 . 120.8 no
N4 . N3 . C8 . 111.4(2) yes
N3 . N4 . Zn1 . 119.84(18) yes
N3 . N4 . C9 . 117.7(2) yes
Zn1 . N4 . C9 . 122.3(2) yes
Zn1 . N5 . C10 . 111.63(19) yes
Zn1 . N5 . C14 . 129.1(2) yes
C10 . N5 . C14 . 119.2(3) yes
Zn1 . N6 . C15 . 128.7(2) yes
Zn1 . N6 . C22 . 112.44(17) yes
C15 . N6 . C22 . 118.6(2) yes
C15 . N7 . C16 . 121.2(3) yes
C15 . N7 . H71 . 119.0 no
C16 . N7 . H71 . 119.6 no
N9 . N8 . C22 . 110.4(2) yes
N8 . N9 . Zn1 . 120.55(16) yes
N8 . N9 . C23 . 118.8(2) yes
Zn1 . N9 . C23 . 120.0(2) yes
Zn1 . N10 . C24 . 111.45(19) yes
Zn1 . N10 . C28 . 129.2(2) yes
C24 . N10 . C28 . 119.3(3) yes
O1 . N11 . O2 . 120.8(5) yes
O1 . N11 . O3 . 119.3(4) yes
O2 . N11 . O3 . 119.8(5) yes
C29 . O4 . H294 . 111.7 no
N2 . C1 . N1 . 126.5(3) yes
N2 . C1 . H11 . 117.1 no
N1 . C1 . H11 . 116.4 no
N2 . C2 . C3 . 120.1(4) yes
N2 . C2 . C7 . 118.9(3) yes
C3 . C2 . C7 . 121.0(4) yes
C2 . C3 . C4 . 118.0(4) yes
C2 . C3 . H31 . 120.2 no
C4 . C3 . H31 . 121.8 no
C3 . C4 . C5 . 122.2(4) yes
C3 . C4 . H41 . 117.9 no
C5 . C4 . H41 . 119.9 no
C4 . C5 . C6 . 120.0(4) yes
C4 . C5 . H51 . 119.9 no
C6 . C5 . H51 . 120.2 no
C5 . C6 . C7 . 120.1(4) yes
C5 . C6 . H61 . 120.2 no
C7 . C6 . H61 . 119.6 no
C6 . C7 . C2 . 118.6(3) yes
C6 . C7 . C8 . 122.5(3) yes
C2 . C7 . C8 . 118.9(3) yes
C7 . C8 . N1 . 118.0(3) yes
C7 . C8 . N3 . 119.9(3) yes
N1 . C8 . N3 . 122.0(3) yes
N4 . C9 . C10 . 114.6(3) yes
N4 . C9 . H91 . 124.5 no
C10 . C9 . H91 . 120.6 no
C9 . C10 . N5 . 117.2(3) yes
C9 . C10 . C11 . 123.0(3) yes
N5 . C10 . C11 . 119.8(3) yes
C10 . C11 . C12 . 121.0(3) yes
C10 . C11 . F1 . 118.7(3) yes
C12 . C11 . F1 . 120.2(3) yes
C11 . C12 . C13 . 118.4(3) yes
C11 . C12 . H121 . 120.0 no
C13 . C12 . H121 . 121.6 no
C12 . C13 . C14 . 118.3(3) yes
C12 . C13 . H131 . 120.1 no
C14 . C13 . H131 . 121.6 no
C13 . C14 . N5 . 123.1(3) yes
C13 . C14 . H141 . 119.7 no
N5 . C14 . H141 . 117.2 no
N7 . C15 . N6 . 125.0(3) yes
N7 . C15 . H151 . 116.3 no
N6 . C15 . H151 . 118.6 no
N7 . C16 . C17 . 121.2(3) yes
N7 . C16 . C21 . 118.0(3) yes
C17 . C16 . C21 . 120.8(3) yes
C16 . C17 . C18 . 119.4(3) yes
C16 . C17 . H171 . 119.9 no
C18 . C17 . H171 . 120.7 no
C17 . C18 . C19 . 120.4(3) yes
C17 . C18 . H181 . 120.4 no
C19 . C18 . H181 . 119.2 no
C18 . C19 . C20 . 120.5(3) yes
C18 . C19 . H191 . 119.3 no
C20 . C19 . H191 . 120.3 no
C19 . C20 . C21 . 120.8(3) yes
C19 . C20 . H201 . 119.6 no
C21 . C20 . H201 . 119.6 no
C20 . C21 . C16 . 118.2(3) yes
C20 . C21 . C22 . 123.4(3) yes
C16 . C21 . C22 . 118.5(3) yes
C21 . C22 . N6 . 118.7(2) yes
C21 . C22 . N8 . 118.9(2) yes
N6 . C22 . N8 . 122.4(2) yes
N9 . C23 . C24 . 116.6(3) yes
N9 . C23 . H231 . 121.8 no
C24 . C23 . H231 . 121.6 no
C23 . C24 . N10 . 116.9(3) yes
C23 . C24 . C25 . 123.5(3) yes
N10 . C24 . C25 . 119.6(3) yes
C24 . C25 . C26 . 121.2(4) yes
C24 . C25 . F2 . 118.6(3) yes
C26 . C25 . F2 . 120.1(3) yes
C25 . C26 . C27 . 118.2(4) yes
C25 . C26 . H261 . 121.4 no
C27 . C26 . H261 . 120.4 no
C26 . C27 . C28 . 118.8(4) yes
C26 . C27 . H271 . 120.7 no
C28 . C27 . H271 . 120.5 no
C27 . C28 . N10 . 122.9(4) yes
C27 . C28 . H281 . 118.6 no
N10 . C28 . H281 . 118.6 no
O4 . C29 . H291 . 107.5 no
O4 . C29 . H292 . 107.3 no
H291 . C29 . H292 . 111.6 no
O4 . C29 . H293 . 108.4 no
H291 . C29 . H293 . 111.0 no
H292 . C29 . H293 . 110.9 no
F8 . P1 . F4 . 79.9(3) yes
F8 . P1 . F5 . 79.3(3) yes
F4 . P1 . F5 . 82.3(3) yes
F8 . P1 . F3 . 85.8(4) yes
F4 . P1 . F3 . 157.8(4) yes
F5 . P1 . F3 . 78.3(3) yes
F8 . P1 . F6 . 86.9(3) yes
F4 . P1 . F6 . 91.1(4) yes
F5 . P1 . F6 . 165.5(3) yes
F3 . P1 . F6 . 105.2(4) yes
F8 . P1 . F7 . 174.1(4) yes
F4 . P1 . F7 . 98.7(4) yes
F5 . P1 . F7 . 94.9(4) yes
F3 . P1 . F7 . 93.8(4) yes
F6 . P1 . F7 . 98.9(4) 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
N2 . H21 . O4 2_665 158 0.85 1.88 2.684(6) yes
C3 . H31 . O4 2_665 132 0.91 2.53 3.216(6) yes
N7 . H71 . N11 2_666 166 0.84 2.54 3.357(6) yes
N7 . H71 . O2 2_666 140 0.84 2.41 3.099(6) yes
N7 . H71 . O3 2_666 166 0.84 1.98 2.795(6) yes
C9 . H91 . O1 2_766 155 1.01 2.48 3.429(6) yes
C29 . H292 . O1 . 129 0.96 2.46 3.161(6) yes
O4 . H294 . N11 . 154 0.83 2.47 3.239(6) yes
O4 . H294 . O2 . 180 0.83 1.79 2.621(6) yes


# 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_I_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2190749'
loop_
_audit_author_name
_audit_author_address
'Antonios Hatzidimitriou'
;Aristotle University of Thessaloniki
Greece
;
_audit_update_record             
;
2022-07-16 deposited with the CCDC.	2022-10-18 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                   11.961(4)
_cell_length_b                   8.170(3)
_cell_length_c                   20.759(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.555(11)
_cell_angle_gamma                90
_cell_volume                     1972.1(12)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  ?
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'
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'
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'
Mn 0.3368 0.7283 11.2819 5.3409 7.3573 0.3432 3.0193 17.8674 2.2441 83.7543
1.0896 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C15 H15 Cl1.50 F1.50 Mn1.50 N3 O3 
# Dc =      1.51 Fooo =    906.00 Mu =     12.09 M =    449.37
# Found Formula = C16 H18 Cl2 F1 Mn1 N5 O2 
# Dc =      1.54 FOOO =    932.00 Mu =      9.71 M =    457.18

_chemical_formula_sum            'C16 H18 Cl2 F1 Mn1 N5 O2'
_chemical_formula_moiety         'C16 H18 Cl2 F1 Mn1 N5 O2'
_chemical_compound_source        ?
_chemical_formula_weight         457.18


_cell_measurement_reflns_used    312
_cell_measurement_theta_min      10
_cell_measurement_theta_max      20
_cell_measurement_temperature    295

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.140
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_max          0.220

_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             932
_exptl_absorpt_coefficient_mu    0.971

# Sheldrick geometric approximatio 0.83 0.87 
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.87
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      295
_diffrn_reflns_number            20642
_reflns_number_total             3753
_diffrn_reflns_av_R_equivalents  0.037
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3753 
# Theoretical number of reflections is about 7584 


_diffrn_reflns_theta_min         1.805
_diffrn_reflns_theta_max         25.795
_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        25.279
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              -14
_reflns_limit_h_max              14
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              24

_oxford_diffrn_Wilson_B_factor   2.99
_oxford_diffrn_Wilson_scale      150.04

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

_refine_diff_density_min         -0.37
_refine_diff_density_max         0.47


# 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>2.0\s(I)
_refine_ls_number_reflns         2796
_refine_ls_number_restraints     0
_refine_ls_number_parameters     244
_oxford_refine_ls_R_factor_ref   0.0414
_refine_ls_wR_factor_ref         0.0651
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_shift/su_max          0.0004954
_refine_ls_shift/su_mean         0.0000306


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3738
_refine_ls_R_factor_all          0.0662
_refine_ls_wR_factor_all         0.0721

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2796
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_gt          0.0651

# 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 Fsqd
_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: 
 1.16 1.33 0.334 
;

# 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
Mn1 Mn 0.42956(4) 0.65843(7) 0.65592(2) 0.0321 1.0000 Uani . . . . . .
Cl1 Cl 0.52235(8) 0.65278(16) 0.77235(4) 0.0617 1.0000 Uani . . . . . .
Cl2 Cl 0.29638(8) 0.88396(12) 0.66258(5) 0.0477 1.0000 Uani . . . . . .
N1 N 0.2851(2) 0.4772(3) 0.62399(11) 0.0305 1.0000 Uani . . . . . .
N2 N 0.1365(2) 0.3122(4) 0.64192(12) 0.0392 1.0000 Uani . . . . . .
N3 N 0.2951(2) 0.5332(3) 0.51371(11) 0.0311 1.0000 Uani . . . . . .
N4 N 0.3861(2) 0.6280(3) 0.54591(11) 0.0290 1.0000 Uani . . . . . .
N5 N 0.5619(2) 0.8008(3) 0.61361(12) 0.0335 1.0000 Uani . . . . . .
O1 O 0.54746(19) 0.4314(3) 0.64568(10) 0.0414 1.0000 Uani . . . . . .
O2 O 0.4805(3) 0.1606(4) 0.69972(13) 0.0738 1.0000 Uani . . . . . .
C1 C 0.2290(3) 0.4020(4) 0.66241(15) 0.0352 1.0000 Uani . . . . . .
C2 C 0.0874(3) 0.2924(4) 0.57445(15) 0.0331 1.0000 Uani . . . . . .
C3 C -0.0139(3) 0.2054(5) 0.55227(17) 0.0485 1.0000 Uani . . . . . .
C4 C -0.0597(3) 0.1932(5) 0.48575(17) 0.0513 1.0000 Uani . . . . . .
C5 C -0.0067(3) 0.2642(5) 0.44065(17) 0.0471 1.0000 Uani . . . . . .
C6 C 0.0929(3) 0.3509(5) 0.46234(15) 0.0392 1.0000 Uani . . . . . .
C7 C 0.1420(2) 0.3666(4) 0.53010(14) 0.0304 1.0000 Uani . . . . . .
C8 C 0.2443(2) 0.4625(4) 0.55588(14) 0.0290 1.0000 Uani . . . . . .
C9 C 0.4505(2) 0.6900(4) 0.51171(14) 0.0318 1.0000 Uani . . . . . .
C10 C 0.5464(2) 0.7884(4) 0.54734(15) 0.0301 1.0000 Uani . . . . . .
C11 C 0.6205(3) 0.8682(5) 0.51600(16) 0.0413 1.0000 Uani . . . . . .
C12 C 0.7096(3) 0.9604(5) 0.5508(2) 0.0578 1.0000 Uani . . . . . .
C13 C 0.7247(3) 0.9711(5) 0.6181(2) 0.0568 1.0000 Uani . . . . . .
C14 C 0.6491(3) 0.8904(5) 0.64741(18) 0.0459 1.0000 Uani . . . . . .
C15 C 0.6684(3) 0.4304(6) 0.6700(2) 0.0606 1.0000 Uani . . . . . .
C16 C 0.4955(5) 0.1600(7) 0.7681(2) 0.0901 1.0000 Uani . . . . . .
F1 F 0.60297(19) 0.8547(3) 0.45002(10) 0.0624 1.0000 Uani . . . . . .
H11 H 0.5226 0.3527 0.6615 0.0607 1.0000 Uiso R . . . . .
H12 H 0.2584 0.4116 0.7077 0.0404 1.0000 Uiso R . . . . .
H21 H 0.1044 0.2687 0.6699 0.0462 1.0000 Uiso R . . . . .
H22 H 0.4180 0.1133 0.6863 0.1098 1.0000 Uiso R . . . . .
H31 H -0.0485 0.1564 0.5823 0.0549 1.0000 Uiso R . . . . .
H41 H -0.1275 0.1340 0.4702 0.0589 1.0000 Uiso R . . . . .
H51 H -0.0388 0.2542 0.3956 0.0549 1.0000 Uiso R . . . . .
H61 H 0.1276 0.3987 0.4320 0.0457 1.0000 Uiso R . . . . .
H91 H 0.4379 0.6751 0.4664 0.0363 1.0000 Uiso R . . . . .
H121 H 0.7596 1.0133 0.5292 0.0691 1.0000 Uiso R . . . . .
H131 H 0.7841 1.0320 0.6431 0.0661 1.0000 Uiso R . . . . .
H141 H 0.6591 0.8967 0.6929 0.0525 1.0000 Uiso R . . . . .
H151 H 0.7054 0.4714 0.6365 0.0914 1.0000 Uiso R . . . . .
H152 H 0.6946 0.3190 0.6801 0.0912 1.0000 Uiso R . . . . .
H153 H 0.6906 0.4976 0.7084 0.0915 1.0000 Uiso R . . . . .
H161 H 0.5660 0.2125 0.7882 0.1061 1.0000 Uiso R . . . . .
H162 H 0.4968 0.0500 0.7836 0.1061 1.0000 Uiso R . . . . .
H163 H 0.4337 0.2176 0.7794 0.1061 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.085929(16)
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
Mn1 . Cl1 . 2.4121(12) yes
Mn1 . Cl2 . 2.4607(12) yes
Mn1 . N1 . 2.254(3) yes
Mn1 . N4 . 2.234(2) yes
Mn1 . N5 . 2.299(3) yes
Mn1 . O1 . 2.370(2) yes
N1 . C1 . 1.309(4) yes
N1 . C8 . 1.389(4) yes
N2 . C1 . 1.313(4) yes
N2 . C2 . 1.395(4) yes
N2 . H21 . 0.845 no
N3 . N4 . 1.375(3) yes
N3 . C8 . 1.311(4) yes
N4 . C9 . 1.269(4) yes
N5 . C10 . 1.348(4) yes
N5 . C14 . 1.331(4) yes
O1 . C15 . 1.416(4) yes
O1 . H11 . 0.809 no
O2 . C16 . 1.390(5) yes
O2 . H22 . 0.829 no
C1 . H12 . 0.928 no
C2 . C3 . 1.387(4) yes
C2 . C7 . 1.387(4) yes
C3 . C4 . 1.365(5) yes
C3 . H31 . 0.917 no
C4 . C5 . 1.376(5) yes
C4 . H41 . 0.934 no
C5 . C6 . 1.368(5) yes
C5 . H51 . 0.927 no
C6 . C7 . 1.397(4) yes
C6 . H61 . 0.918 no
C7 . C8 . 1.445(4) yes
C9 . C10 . 1.453(4) yes
C9 . H91 . 0.924 no
C10 . C11 . 1.380(4) yes
C11 . C12 . 1.366(5) yes
C11 . F1 . 1.341(4) yes
C12 . C13 . 1.369(5) yes
C12 . H121 . 0.933 no
C13 . C14 . 1.371(5) yes
C13 . H131 . 0.921 no
C14 . H141 . 0.925 no
C15 . H151 . 0.967 no
C15 . H152 . 0.969 no
C15 . H153 . 0.953 no
C16 . H161 . 0.951 no
C16 . H162 . 0.954 no
C16 . H163 . 0.951 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
Cl1 . Mn1 . Cl2 . 96.31(5) yes
Cl1 . Mn1 . N1 . 115.03(7) yes
Cl2 . Mn1 . N1 . 92.66(8) yes
Cl1 . Mn1 . N4 . 164.65(7) yes
Cl2 . Mn1 . N4 . 98.18(8) yes
N1 . Mn1 . N4 . 69.37(9) yes
Cl1 . Mn1 . N5 . 101.31(7) yes
Cl2 . Mn1 . N5 . 98.94(8) yes
N1 . Mn1 . N5 . 140.30(9) yes
N4 . Mn1 . N5 . 71.44(9) yes
Cl1 . Mn1 . O1 . 86.05(7) yes
Cl2 . Mn1 . O1 . 176.29(6) yes
N1 . Mn1 . O1 . 83.74(9) yes
N4 . Mn1 . O1 . 79.74(9) yes
N5 . Mn1 . O1 . 83.35(9) yes
Mn1 . N1 . C1 . 126.6(2) yes
Mn1 . N1 . C8 . 114.73(18) yes
C1 . N1 . C8 . 118.2(3) yes
C1 . N2 . C2 . 121.0(3) yes
C1 . N2 . H21 . 119.8 no
C2 . N2 . H21 . 119.2 no
N4 . N3 . C8 . 111.2(2) yes
Mn1 . N4 . N3 . 121.85(17) yes
Mn1 . N4 . C9 . 120.1(2) yes
N3 . N4 . C9 . 117.9(2) yes
Mn1 . N5 . C10 . 114.14(19) yes
Mn1 . N5 . C14 . 127.0(2) yes
C10 . N5 . C14 . 118.9(3) yes
Mn1 . O1 . C15 . 123.5(2) yes
Mn1 . O1 . H11 . 107.6 no
C15 . O1 . H11 . 107.0 no
C16 . O2 . H22 . 103.3 no
N2 . C1 . N1 . 125.3(3) yes
N2 . C1 . H12 . 117.8 no
N1 . C1 . H12 . 116.9 no
N2 . C2 . C3 . 121.5(3) yes
N2 . C2 . C7 . 117.6(3) yes
C3 . C2 . C7 . 120.9(3) yes
C2 . C3 . C4 . 119.0(3) yes
C2 . C3 . H31 . 119.8 no
C4 . C3 . H31 . 121.2 no
C3 . C4 . C5 . 121.2(3) yes
C3 . C4 . H41 . 119.9 no
C5 . C4 . H41 . 118.9 no
C4 . C5 . C6 . 119.9(3) yes
C4 . C5 . H51 . 120.1 no
C6 . C5 . H51 . 120.0 no
C5 . C6 . C7 . 120.5(3) yes
C5 . C6 . H61 . 119.5 no
C7 . C6 . H61 . 120.0 no
C6 . C7 . C2 . 118.4(3) yes
C6 . C7 . C8 . 122.8(3) yes
C2 . C7 . C8 . 118.7(3) yes
C7 . C8 . N1 . 119.3(3) yes
C7 . C8 . N3 . 118.5(3) yes
N1 . C8 . N3 . 122.3(3) yes
N4 . C9 . C10 . 116.5(3) yes
N4 . C9 . H91 . 122.7 no
C10 . C9 . H91 . 120.8 no
C9 . C10 . N5 . 117.7(3) yes
C9 . C10 . C11 . 122.6(3) yes
N5 . C10 . C11 . 119.7(3) yes
C10 . C11 . C12 . 121.3(3) yes
C10 . C11 . F1 . 118.6(3) yes
C12 . C11 . F1 . 120.1(3) yes
C11 . C12 . C13 . 118.3(3) yes
C11 . C12 . H121 . 120.7 no
C13 . C12 . H121 . 121.0 no
C12 . C13 . C14 . 118.7(3) yes
C12 . C13 . H131 . 120.6 no
C14 . C13 . H131 . 120.8 no
C13 . C14 . N5 . 123.1(3) yes
C13 . C14 . H141 . 119.1 no
N5 . C14 . H141 . 117.8 no
O1 . C15 . H151 . 110.1 no
O1 . C15 . H152 . 109.6 no
H151 . C15 . H152 . 107.6 no
O1 . C15 . H153 . 110.9 no
H151 . C15 . H153 . 108.4 no
H152 . C15 . H153 . 110.2 no
O2 . C16 . H161 . 109.6 no
O2 . C16 . H162 . 109.6 no
H161 . C16 . H162 . 109.6 no
O2 . C16 . H163 . 109.2 no
H161 . C16 . H163 . 109.3 no
H162 . C16 . H163 . 109.6 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
O1 . H11 . O2 . 174 0.81 1.88 2.686(5) yes
C9 . H91 . O1 2_666 162 0.92 2.53 3.420(5) yes


# 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_I_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2190747'
loop_
_audit_author_name
_audit_author_address
'Antonios Hatzidimitriou'
;Aristotle University of Thessaloniki
Greece
;
_audit_update_record             
;
2022-07-16 deposited with the CCDC.	2022-10-18 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                   13.149(6)
_cell_length_b                   15.905(7)
_cell_length_c                   19.736(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.53(2)
_cell_angle_gamma                90
_cell_volume                     4092(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1 '
_symmetry_space_group_name_Hall  ?
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 0.0033 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'
Cd -0.8075 1.2024 19.2214 0.5946 17.6444 6.9089 4.4610 24.7008 1.6029 87.4825
5.0694 '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'


_cell_formula_units_Z            8

# Given Formula = C18 H16 Cd1 F0.25 N6 O7 
# Dc =      1.77 Fooo =   2178.00 Mu =     11.25 M =    545.51
# Found Formula = C15 H16 Cd1 F1 N7 O8 
# Dc =      1.80 FOOO =   2208.00 Mu =     11.36 M =    553.73

_chemical_formula_sum            'C15 H16 Cd1 F1 N7 O8'
_chemical_formula_moiety         'C15 H16 Cd1 F1 N7 O8'
_chemical_compound_source        ?
_chemical_formula_weight         553.73


_cell_measurement_reflns_used    229
_cell_measurement_theta_min      10
_cell_measurement_theta_max      20
_cell_measurement_temperature    295

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.160
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_max          0.230

_exptl_crystal_density_diffrn    1.798
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2208
_exptl_absorpt_coefficient_mu    1.136

# Sheldrick geometric approximatio 0.78 0.83 
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.83
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      295
_diffrn_reflns_number            22737
_reflns_number_total             4170
_diffrn_reflns_av_R_equivalents  0.030
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4170 
# Theoretical number of reflections is about 8415 


_diffrn_reflns_theta_min         2.020
_diffrn_reflns_theta_max         26.424
_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        25.896
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_reflns_limit_h_min              -16
_reflns_limit_h_max              16
_reflns_limit_k_min              0
_reflns_limit_k_max              19
_reflns_limit_l_min              0
_reflns_limit_l_max              24

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -1.75
_refine_diff_density_max         0.63


# 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>2.0\s(I)
_refine_ls_number_reflns         3542
_refine_ls_number_restraints     6
_refine_ls_number_parameters     289
_oxford_refine_ls_R_factor_ref   0.0330
_refine_ls_wR_factor_ref         0.0515
_refine_ls_goodness_of_fit_ref   1.0002
_refine_ls_shift/su_max          0.0018520
_refine_ls_shift/su_mean         0.0000455


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4153
_refine_ls_R_factor_all          0.0429
_refine_ls_wR_factor_all         0.0538

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3542
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_gt          0.0515

# 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 Fsqd
_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: 
 13.3 14.5 6.92 
;

# 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
Cd1 Cd 0.36197(2) 0.572528(15) 0.596810(11) 0.0313 1.0000 Uani . U . . . .
N1 N 0.3577(2) 0.69425(16) 0.66364(13) 0.0296 1.0000 Uani . . . . . .
N2 N 0.3629(2) 0.84028(17) 0.67598(14) 0.0354 1.0000 Uani . . . . . .
N3 N 0.3699(2) 0.60761(15) 0.76166(12) 0.0257 1.0000 Uani . . . . . .
N4 N 0.3666(2) 0.54404(15) 0.71345(12) 0.0260 1.0000 Uani . . . . . .
N5 N 0.3652(2) 0.42489(17) 0.61569(12) 0.0318 1.0000 Uani . . . . . .
N6 N 0.3684(2) 0.61686(18) 0.45801(13) 0.0362 1.0000 Uani . . . . . .
N7 N 0.1463(3) 0.5242(2) 0.9161(2) 0.0629 1.0000 Uani . . . . . .
O1 O 0.3561(3) 0.67318(16) 0.50031(13) 0.0613 1.0000 Uani . . . . . .
O2 O 0.3784(2) 0.54215(15) 0.48082(11) 0.0398 1.0000 Uani . . . . . .
O3 O 0.3701(2) 0.63166(19) 0.39752(12) 0.0589 1.0000 Uani . . . . . .
O4 O 0.18548(17) 0.57525(15) 0.57059(10) 0.0348 1.0000 Uani . U . . . .
O5 O 0.53891(17) 0.56874(16) 0.60453(11) 0.0385 1.0000 Uani . . . . . .
O6 O 0.1448(5) 0.5366(3) 0.8549(2) 0.1250 1.0000 Uani . . . . . .
O7 O 0.1573(3) 0.5809(2) 0.95841(18) 0.0908 1.0000 Uani . . . . . .
O8 O 0.1349(2) 0.45007(17) 0.93486(15) 0.0638 1.0000 Uani . . . . . .
C1 C 0.3559(3) 0.7712(2) 0.63888(17) 0.0340 1.0000 Uani . . . . . .
C2 C 0.3722(2) 0.8366(2) 0.74635(17) 0.0292 1.0000 Uani . . . . . .
C3 C 0.3812(3) 0.9101(2) 0.78535(19) 0.0405 1.0000 Uani . . . . . .
C4 C 0.3909(3) 0.9045(2) 0.8549(2) 0.0470 1.0000 Uani . . . . . .
C5 C 0.3898(3) 0.8274(2) 0.88607(19) 0.0471 1.0000 Uani . . . . . .
C6 C 0.3801(3) 0.7541(2) 0.84905(17) 0.0388 1.0000 Uani . . . . . .
C7 C 0.3720(2) 0.75748(19) 0.77709(15) 0.0263 1.0000 Uani . . . . . .
C8 C 0.3660(2) 0.68321(18) 0.73362(15) 0.0238 1.0000 Uani . . . . . .
C9 C 0.3693(2) 0.46786(19) 0.73371(15) 0.0271 1.0000 Uani . . . . . .
C10 C 0.3704(2) 0.40151(19) 0.68182(15) 0.0274 1.0000 Uani . . . . . .
C11 C 0.3761(3) 0.3173(2) 0.69847(17) 0.0330 1.0000 Uani . . . . . .
C12 C 0.3775(3) 0.2551(2) 0.65008(19) 0.0422 1.0000 Uani . . . . . .
C13 C 0.3730(3) 0.2811(2) 0.58304(19) 0.0485 1.0000 Uani . . . . . .
C14 C 0.3659(3) 0.3660(2) 0.56776(17) 0.0393 1.0000 Uani . . . . . .
C15 C 0.1181(4) 0.6365(3) 0.5913(3) 0.0847 1.0000 Uani . . . . . .
H11 H 0.3477 0.7767 0.5914 0.0419 1.0000 Uiso R . . . . .
H21 H 0.3616 0.8866 0.6561 0.0436 1.0000 Uiso R . . . . .
H31 H 0.3800 0.9616 0.7632 0.0487 1.0000 Uiso R . . . . .
H41 H 0.3982 0.9538 0.8809 0.0563 1.0000 Uiso R . . . . .
H42 H 0.1674 0.5601 0.5293 0.0745 1.0000 Uiso R . . . . .
H51 H 0.3966 0.8243 0.9338 0.0572 1.0000 Uiso R . . . . .
H52 H 0.5730 0.5728 0.6439 0.0578 1.0000 Uiso R . . . . .
H53 H 0.5682 0.5306 0.5833 0.0568 1.0000 Uiso R . . . . .
H61 H 0.3781 0.7010 0.8707 0.0466 1.0000 Uiso R . . . . .
H91 H 0.3707 0.4535 0.7792 0.0325 1.0000 Uiso R . . . . .
H121 H 0.3824 0.1985 0.6618 0.0512 1.0000 Uiso R . . . . .
H131 H 0.3747 0.2423 0.5476 0.0578 1.0000 Uiso R . . . . .
H141 H 0.3607 0.3837 0.5217 0.0481 1.0000 Uiso R . . . . .
H151 H 0.1246 0.6859 0.5659 0.1304 1.0000 Uiso R . . . . .
H152 H 0.1373 0.6493 0.6383 0.1300 1.0000 Uiso R . . . . .
H153 H 0.0491 0.6192 0.5850 0.1301 1.0000 Uiso R . . . . .
F1 F 0.37985(19) 0.29503(12) 0.76483(10) 0.0489 1.0000 Uani . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.20422(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
Cd1 . N1 . 2.348(3) yes
Cd1 . N4 . 2.339(3) yes
Cd1 . N5 . 2.377(3) yes
Cd1 . O1 . 2.482(3) yes
Cd1 . O2 . 2.377(2) yes
Cd1 . O4 . 2.311(2) yes
Cd1 . O5 . 2.312(2) yes
N1 . C1 . 1.317(4) yes
N1 . C8 . 1.382(4) yes
N2 . C1 . 1.317(4) yes
N2 . C2 . 1.379(4) yes
N2 . H21 . 0.834 no
N3 . N4 . 1.385(3) yes
N3 . C8 . 1.322(4) yes
N4 . C9 . 1.275(4) yes
N5 . C10 . 1.350(4) yes
N5 . C14 . 1.332(4) yes
N6 . O1 . 1.250(4) yes
N6 . O2 . 1.271(3) yes
N6 . O3 . 1.220(3) yes
N7 . O6 . 1.222(5) yes
N7 . O7 . 1.226(4) yes
N7 . O8 . 1.250(4) yes
O4 . C15 . 1.413(5) yes
O4 . H42 . 0.853 no
O5 . H52 . 0.847 no
O5 . H53 . 0.857 no
C1 . H11 . 0.933 no
C2 . C3 . 1.396(4) yes
C2 . C7 . 1.397(4) yes
C3 . C4 . 1.364(5) yes
C3 . H31 . 0.929 no
C4 . C5 . 1.374(5) yes
C4 . H41 . 0.936 no
C5 . C6 . 1.373(5) yes
C5 . H51 . 0.935 no
C6 . C7 . 1.411(4) yes
C6 . H61 . 0.947 no
C7 . C8 . 1.456(4) yes
C9 . C10 . 1.472(4) yes
C9 . H91 . 0.924 no
C10 . C11 . 1.378(4) yes
C11 . C12 . 1.378(5) yes
C11 . F1 . 1.352(4) yes
C12 . C13 . 1.380(5) yes
C12 . H121 . 0.929 no
C13 . C14 . 1.384(5) yes
C13 . H131 . 0.935 no
C14 . H141 . 0.947 no
C15 . H151 . 0.943 no
C15 . H152 . 0.950 no
C15 . H153 . 0.941 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 . Cd1 . N4 . 66.81(9) yes
N1 . Cd1 . N5 . 136.71(9) yes
N4 . Cd1 . N5 . 69.93(8) yes
N1 . Cd1 . O1 . 84.18(9) yes
N4 . Cd1 . O1 . 150.98(8) yes
N5 . Cd1 . O1 . 139.09(8) yes
N1 . Cd1 . O2 . 136.11(9) yes
N4 . Cd1 . O2 . 156.13(8) yes
N5 . Cd1 . O2 . 87.02(8) yes
O1 . Cd1 . O2 . 52.38(9) yes
N1 . Cd1 . O4 . 90.74(9) yes
N4 . Cd1 . O4 . 96.88(9) yes
N5 . Cd1 . O4 . 92.89(9) yes
O1 . Cd1 . O4 . 83.51(10) yes
O2 . Cd1 . O4 . 90.21(9) yes
N1 . Cd1 . O5 . 94.73(9) yes
N4 . Cd1 . O5 . 91.94(9) yes
N5 . Cd1 . O5 . 88.09(10) yes
O1 . Cd1 . O5 . 89.83(11) yes
O2 . Cd1 . O5 . 80.82(9) yes
O4 . Cd1 . O5 . 170.91(7) yes
Cd1 . N1 . C1 . 124.0(2) yes
Cd1 . N1 . C8 . 116.87(19) yes
C1 . N1 . C8 . 118.9(3) yes
C1 . N2 . C2 . 121.0(3) yes
C1 . N2 . H21 . 118.7 no
C2 . N2 . H21 . 120.3 no
N4 . N3 . C8 . 112.4(2) yes
N3 . N4 . Cd1 . 121.94(18) yes
N3 . N4 . C9 . 118.8(2) yes
Cd1 . N4 . C9 . 119.3(2) yes
Cd1 . N5 . C10 . 114.9(2) yes
Cd1 . N5 . C14 . 125.8(2) yes
C10 . N5 . C14 . 119.2(3) yes
O1 . N6 . O2 . 116.7(3) yes
O1 . N6 . O3 . 122.4(3) yes
O2 . N6 . O3 . 120.9(3) yes
O6 . N7 . O7 . 122.7(4) yes
O6 . N7 . O8 . 117.4(4) yes
O7 . N7 . O8 . 120.0(4) yes
Cd1 . O1 . N6 . 93.24(19) yes
Cd1 . O2 . N6 . 97.64(17) yes
Cd1 . O4 . C15 . 126.7(3) yes
Cd1 . O4 . H42 . 110.8 no
C15 . O4 . H42 . 111.4 no
Cd1 . O5 . H52 . 117.7 no
Cd1 . O5 . H53 . 120.0 no
H52 . O5 . H53 . 106.5 no
N1 . C1 . N2 . 124.9(3) yes
N1 . C1 . H11 . 117.0 no
N2 . C1 . H11 . 118.1 no
N2 . C2 . C3 . 120.6(3) yes
N2 . C2 . C7 . 118.1(3) yes
C3 . C2 . C7 . 121.3(3) yes
C2 . C3 . C4 . 119.4(3) yes
C2 . C3 . H31 . 119.0 no
C4 . C3 . H31 . 121.6 no
C3 . C4 . C5 . 120.2(3) yes
C3 . C4 . H41 . 119.1 no
C5 . C4 . H41 . 120.6 no
C4 . C5 . C6 . 121.7(3) yes
C4 . C5 . H51 . 119.5 no
C6 . C5 . H51 . 118.8 no
C5 . C6 . C7 . 119.5(3) yes
C5 . C6 . H61 . 121.5 no
C7 . C6 . H61 . 119.0 no
C6 . C7 . C2 . 117.9(3) yes
C6 . C7 . C8 . 123.6(3) yes
C2 . C7 . C8 . 118.5(3) yes
C7 . C8 . N1 . 118.5(3) yes
C7 . C8 . N3 . 119.7(3) yes
N1 . C8 . N3 . 121.8(3) yes
N4 . C9 . C10 . 117.7(3) yes
N4 . C9 . H91 . 122.4 no
C10 . C9 . H91 . 119.8 no
C9 . C10 . N5 . 118.1(3) yes
C9 . C10 . C11 . 122.4(3) yes
N5 . C10 . C11 . 119.5(3) yes
C10 . C11 . C12 . 122.6(3) yes
C10 . C11 . F1 . 118.7(3) yes
C12 . C11 . F1 . 118.7(3) yes
C11 . C12 . C13 . 116.5(3) yes
C11 . C12 . H121 . 122.1 no
C13 . C12 . H121 . 121.4 no
C12 . C13 . C14 . 119.6(3) yes
C12 . C13 . H131 . 121.1 no
C14 . C13 . H131 . 119.3 no
C13 . C14 . N5 . 122.6(3) yes
C13 . C14 . H141 . 119.7 no
N5 . C14 . H141 . 117.8 no
O4 . C15 . H151 . 108.5 no
O4 . C15 . H152 . 109.5 no
H151 . C15 . H152 . 108.1 no
O4 . C15 . H153 . 113.0 no
H151 . C15 . H153 . 109.0 no
H152 . C15 . H153 . 108.6 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
C1 . H11 . O1 . 132 0.93 2.45 3.148(5) yes
N2 . H21 . O6 7_556 157 0.83 2.40 3.181(5) yes
N2 . H21 . O8 7_556 147 0.83 2.07 2.802(5) yes
C3 . H31 . O6 7_556 145 0.93 2.60 3.403(5) yes
C4 . H41 . O4 7_556 148 0.94 2.48 3.307(5) yes
O4 . H42 . N7 6_564 163 0.85 2.59 3.414(5) yes
O4 . H42 . O8 6_564 168 0.85 1.86 2.704(5) yes
O5 . H52 . N3 5_656 165 0.85 1.99 2.822(5) yes
O5 . H53 . O2 2_666 168 0.86 1.91 2.759(5) yes
C6 . H61 . O5 5_656 147 0.95 2.39 3.226(5) yes


# 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_I_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2190746'
loop_
_audit_author_name
_audit_author_address
'Antonios Hatzidimitriou'
;Aristotle University of Thessaloniki
Greece
;
_audit_update_record             
;
2022-07-16 deposited with the CCDC.	2022-10-18 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                   16.205(6)
_cell_length_b                   16.629(6)
_cell_length_c                   23.492(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.765(10)
_cell_angle_gamma                90
_cell_volume                     6122(4)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1 '
_symmetry_space_group_name_Hall  ?
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 0.0033 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'
Ni 0.3393 1.1124 12.8376 3.8785 7.2920 0.2565 4.4438 12.1763 2.3800 66.3421
1.0341 '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'


_cell_formula_units_Z            2

# Given Formula = C120 H120 F1 N24 Ni12 O24 
# Dc =      1.63 Fooo =   3090.00 Mu =     18.82 M =   3005.94
# Found Formula = C113 H88 F8 N48 Ni4 O27 
# Dc =      1.59 FOOO =   3004.00 Mu =      7.14 M =   2937.07

_chemical_formula_sum            'C113 H88 F8 N48 Ni4 O27'
_chemical_formula_moiety         'C113 H88 F8 N48 Ni4 O27'
_chemical_compound_source        ?
_chemical_formula_weight         2937.07


_cell_measurement_reflns_used    227
_cell_measurement_theta_min      10
_cell_measurement_theta_max      20
_cell_measurement_temperature    295

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.150
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_max          0.220

_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             3004
_exptl_absorpt_coefficient_mu    0.714

# Sheldrick geometric approximatio 0.87 0.90 
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.90
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      295
_diffrn_reflns_number            47841
_reflns_number_total             5835
_diffrn_reflns_av_R_equivalents  0.038
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 5835 
# Theoretical number of reflections is about 11741 


_diffrn_reflns_theta_min         1.786
_diffrn_reflns_theta_max         25.791
_diffrn_measured_fraction_theta_max 0.990

_diffrn_reflns_theta_full        25.275
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       24
_reflns_limit_h_min              -19
_reflns_limit_h_max              19
_reflns_limit_k_min              0
_reflns_limit_k_max              20
_reflns_limit_l_min              0
_reflns_limit_l_max              28

_oxford_diffrn_Wilson_B_factor   3.37
_oxford_diffrn_Wilson_scale      1123.51

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

_refine_diff_density_min         -0.47
_refine_diff_density_max         0.51


# 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>2.0\s(I)
_refine_ls_number_reflns         4600
_refine_ls_number_restraints     5
_refine_ls_number_parameters     450
_oxford_refine_ls_R_factor_ref   0.0516
_refine_ls_wR_factor_ref         0.0737
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_shift/su_max          0.0007410
_refine_ls_shift/su_mean         0.0000317


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5808
_refine_ls_R_factor_all          0.0742
_refine_ls_wR_factor_all         0.0825

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4600
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_gt          0.0737

# 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 Fsqd
_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: 
 1.57 1.90 0.515 
;

# 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
Ni1 Ni 0.29154(3) 0.35281(3) 0.632931(16) 0.0444 1.0000 Uani . . . . . .
N1 N 0.33417(15) 0.23953(16) 0.66858(10) 0.0447 1.0000 Uani . . . . . .
N2 N 0.34770(17) 0.10074(17) 0.67236(12) 0.0556 1.0000 Uani . . . . . .
N3 N 0.37451(17) 0.31415(16) 0.75689(10) 0.0500 1.0000 Uani . . . . . .
N4 N 0.34030(16) 0.37478(16) 0.71785(10) 0.0474 1.0000 Uani . . . . . .
N5 N 0.27181(16) 0.47904(16) 0.63671(12) 0.0506 1.0000 Uani . . . . . .
N6 N 0.39239(15) 0.36834(15) 0.59305(10) 0.0428 1.0000 Uani . . . . . .
N7 N 0.53185(16) 0.38542(17) 0.58569(11) 0.0516 1.0000 Uani . . . . . .
N8 N 0.28146(14) 0.35479(17) 0.50605(10) 0.0453 1.0000 Uani . . . . . .
N9 N 0.23627(15) 0.34080(16) 0.54751(10) 0.0457 1.0000 Uani . . . . . .
N10 N 0.16305(17) 0.32324(16) 0.63325(12) 0.0534 1.0000 Uani . . . . . .
N11 N 0.2481(3) 0.3750(3) 0.8565(2) 0.0974 1.0000 Uani . . . . . .
N12 N 0.5000 0.5557 0.7500 0.0893 1.0000 Uani . . . . . .
N13 N 0.0000 0.5000 0.5000 0.1163 1.0000 Uani DS . . . . .
O1 O 0.2865(2) 0.4368(2) 0.85965(16) 0.1144 1.0000 Uani . . . . . .
O2 O 0.1786(2) 0.3565(3) 0.82677(17) 0.1259 1.0000 Uani . . . . . .
O3 O 0.2923(3) 0.3229(3) 0.8803(2) 0.1312 1.0000 Uani . . . . . .
O4 O 0.5000 0.6281(4) 0.7500 0.1545 1.0000 Uani S T . . . .
O5 O 0.4889(2) 0.5230(3) 0.70432(14) 0.1151 1.0000 Uani . . . . . .
O6 O 0.0366(7) 0.5245(5) 0.4623(4) 0.157(4) 0.5000 Uiso D . . . . .
O7 O -0.0667(5) 0.5299(4) 0.5025(4) 0.134(3) 0.5000 Uiso D . . . . .
O8 O 0.0476(5) 0.4771(4) 0.5413(3) 0.0961(19) 0.5000 Uiso . . . . . .
O9 O 0.1541(4) 0.5074(4) 0.4208(3) 0.0959(19) 0.5000 Uiso . . . . . .
O10 O 0.2787(12) 0.8074(12) 0.5322(8) 0.153(6) 0.2500 Uiso . . . . . .
C1 C 0.32619(19) 0.1684(2) 0.64432(14) 0.0495 1.0000 Uani . . . . . .
C2 C 0.3821(2) 0.0992(2) 0.73223(15) 0.0539 1.0000 Uani . . . . . .
C3 C 0.4032(2) 0.0270(2) 0.76361(18) 0.0664 1.0000 Uani . . . . . .
C4 C 0.4373(2) 0.0297(3) 0.82256(19) 0.0728 1.0000 Uani . . . . . .
C5 C 0.4534(2) 0.1018(2) 0.85233(17) 0.0678 1.0000 Uani . . . . . .
C6 C 0.4326(2) 0.1726(2) 0.82294(15) 0.0578 1.0000 Uani . . . . . .
C7 C 0.39565(19) 0.17258(19) 0.76281(14) 0.0490 1.0000 Uani . . . . . .
C8 C 0.36807(19) 0.2446(2) 0.72916(13) 0.0466 1.0000 Uani . . . . . .
C9 C 0.3350(2) 0.4461(2) 0.73692(15) 0.0547 1.0000 Uani . . . . . .
C10 C 0.2992(2) 0.5058(2) 0.69280(15) 0.0530 1.0000 Uani . . . . . .
C11 C 0.2928(2) 0.5864(2) 0.70443(18) 0.0635 1.0000 Uani . . . . . .
C12 C 0.2635(2) 0.6404(2) 0.6604(2) 0.0727 1.0000 Uani . . . . . .
C13 C 0.2380(2) 0.6122(3) 0.6044(2) 0.0745 1.0000 Uani . . . . . .
C14 C 0.2413(2) 0.5309(2) 0.59358(16) 0.0615 1.0000 Uani . . . . . .
C15 C 0.47346(19) 0.37678(19) 0.61631(13) 0.0481 1.0000 Uani . . . . . .
C16 C 0.50718(19) 0.39162(19) 0.52520(13) 0.0473 1.0000 Uani . . . . . .
C17 C 0.5675(2) 0.4049(2) 0.49269(15) 0.0581 1.0000 Uani . . . . . .
C18 C 0.5403(2) 0.4128(2) 0.43318(15) 0.0616 1.0000 Uani . . . . . .
C19 C 0.4552(2) 0.4085(2) 0.40407(14) 0.0599 1.0000 Uani . . . . . .
C20 C 0.3960(2) 0.3955(2) 0.43534(13) 0.0536 1.0000 Uani . . . . . .
C21 C 0.42149(19) 0.38500(19) 0.49693(12) 0.0444 1.0000 Uani . . . . . .
C22 C 0.36201(18) 0.36902(17) 0.53189(12) 0.0407 1.0000 Uani . . . . . .
C23 C 0.15594(19) 0.3285(2) 0.53073(14) 0.0511 1.0000 Uani . . . . . .
C24 C 0.1141(2) 0.3173(2) 0.57807(15) 0.0544 1.0000 Uani . . . . . .
C25 C 0.0273(2) 0.3010(2) 0.56853(19) 0.0702 1.0000 Uani . . . . . .
C26 C -0.0079(3) 0.2891(3) 0.6153(2) 0.0829 1.0000 Uani . . . . . .
C27 C 0.0437(3) 0.2940(3) 0.6705(2) 0.0788 1.0000 Uani . . . . . .
C28 C 0.1292(2) 0.3109(2) 0.67801(17) 0.0675 1.0000 Uani . . . . . .
C29 C 0.2933(14) 0.7437(15) 0.5162(11) 0.118(7) 0.2500 Uiso . . . . . .
F1 F 0.31673(14) 0.61095(13) 0.76108(10) 0.0788 1.0000 Uani . . . . . .
F2 F -0.01987(13) 0.29617(16) 0.51256(12) 0.0920 1.0000 Uani . . . . . .
H11 H 0.3045 0.1665 0.6037 0.0606 1.0000 Uiso R . . . . .
H21 H 0.3412 0.0557 0.6528 0.0709 1.0000 Uiso R . . . . .
H31 H 0.3941 -0.0214 0.7435 0.0848 1.0000 Uiso R . . . . .
H41 H 0.4495 -0.0182 0.8434 0.0950 1.0000 Uiso R . . . . .
H51 H 0.4766 0.1025 0.8929 0.0857 1.0000 Uiso R . . . . .
H61 H 0.4422 0.2209 0.8433 0.0719 1.0000 Uiso R . . . . .
H71 H 0.5847 0.3868 0.6039 0.0650 1.0000 Uiso R . . . . .
H91 H 0.3527 0.4591 0.7767 0.0682 1.0000 Uiso R . . . . .
H92 H 0.1584 0.4827 0.4516 0.1128 0.5000 Uiso R . . . . .
H103 H 0.2561 0.8152 0.5606 0.1547 0.2500 Uiso R . . . . .
H121 H 0.2607 0.6946 0.6687 0.0936 1.0000 Uiso R . . . . .
H131 H 0.2189 0.6473 0.5738 0.0970 1.0000 Uiso R . . . . .
H141 H 0.2209 0.5119 0.5555 0.0769 1.0000 Uiso R . . . . .
H151 H 0.4931 0.3765 0.6575 0.0596 1.0000 Uiso R . . . . .
H171 H 0.6241 0.4096 0.5117 0.0739 1.0000 Uiso R . . . . .
H181 H 0.5807 0.4211 0.4115 0.0787 1.0000 Uiso R . . . . .
H191 H 0.4378 0.4157 0.3636 0.0770 1.0000 Uiso R . . . . .
H201 H 0.3388 0.3928 0.4156 0.0677 1.0000 Uiso R . . . . .
H231 H 0.1257 0.3271 0.4907 0.0628 1.0000 Uiso R . . . . .
H261 H -0.0655 0.2771 0.6091 0.1119 1.0000 Uiso R . . . . .
H271 H 0.0213 0.2870 0.7031 0.1051 1.0000 Uiso R . . . . .
H281 H 0.1646 0.3136 0.7161 0.0861 1.0000 Uiso R . . . . .
H291 H 0.3277 0.7144 0.5483 0.1416 0.2500 Uiso R . . . . .
H294 H 0.2416 0.7158 0.5010 0.1375 0.2500 Uiso R . . . . .
H295 H 0.3227 0.7493 0.4862 0.1416 0.2500 Uiso R . . . . .
H296 H 0.1073 0.5294 0.4111 0.1128 0.5000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.047966(4)
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
Ni1 . N1 . 2.105(3) yes
Ni1 . N4 . 1.984(3) yes
Ni1 . N5 . 2.129(3) yes
Ni1 . N6 . 2.097(2) yes
Ni1 . N9 . 1.988(2) yes
Ni1 . N10 . 2.141(3) yes
N1 . C1 . 1.306(4) yes
N1 . C8 . 1.391(4) yes
N2 . C1 . 1.305(4) yes
N2 . C2 . 1.375(4) yes
N2 . H21 . 0.871 no
N3 . N4 . 1.380(3) yes
N3 . C8 . 1.318(4) yes
N4 . C9 . 1.279(4) yes
N5 . C10 . 1.354(4) yes
N5 . C14 . 1.326(4) yes
N6 . C15 . 1.296(4) yes
N6 . C22 . 1.395(3) yes
N7 . C15 . 1.334(4) yes
N7 . C16 . 1.379(4) yes
N7 . H71 . 0.855 no
N8 . N9 . 1.379(3) yes
N8 . C22 . 1.313(4) yes
N9 . C23 . 1.277(4) yes
N10 . C24 . 1.340(4) yes
N10 . C28 . 1.320(4) yes
N11 . O1 . 1.194(5) yes
N11 . O2 . 1.204(5) yes
N11 . O3 . 1.172(5) yes
N12 . O5 5_656 1.175(3) yes
N12 . O4 . 1.204(6) yes
N12 . O5 . 1.175(3) yes
N13 . O6 2_566 1.253(7) yes
N13 . O7 2_566 1.204(7) yes
N13 . O8 2_566 1.141(7) yes
N13 . O6 . 1.253(7) yes
N13 . O7 . 1.204(7) yes
N13 . O8 . 1.141(7) yes
O9 . H92 . 0.820 no
O9 . H296 . 0.820 no
O10 . C29 . 1.17(2) yes
O10 . H103 . 0.850 no
C1 . H11 . 0.930 no
C2 . C3 . 1.405(5) yes
C2 . C7 . 1.404(5) yes
C3 . C4 . 1.355(5) yes
C3 . H31 . 0.926 no
C4 . C5 . 1.379(5) yes
C4 . H41 . 0.930 no
C5 . C6 . 1.363(5) yes
C5 . H51 . 0.930 no
C6 . C7 . 1.387(4) yes
C6 . H61 . 0.928 no
C7 . C8 . 1.442(4) yes
C9 . C10 . 1.446(5) yes
C9 . H91 . 0.931 no
C10 . C11 . 1.376(5) yes
C11 . C12 . 1.361(5) yes
C11 . F1 . 1.351(4) yes
C12 . C13 . 1.356(6) yes
C12 . H121 . 0.926 no
C13 . C14 . 1.380(5) yes
C13 . H131 . 0.917 no
C14 . H141 . 0.926 no
C15 . H151 . 0.937 no
C16 . C17 . 1.403(4) yes
C16 . C21 . 1.383(4) yes
C17 . C18 . 1.361(5) yes
C17 . H171 . 0.915 no
C18 . C19 . 1.377(5) yes
C18 . H181 . 0.936 no
C19 . C20 . 1.366(4) yes
C19 . H191 . 0.929 no
C20 . C21 . 1.410(4) yes
C20 . H201 . 0.926 no
C21 . C22 . 1.441(4) yes
C23 . C24 . 1.455(4) yes
C23 . H231 . 0.943 no
C24 . C25 . 1.393(5) yes
C25 . C26 . 1.376(6) yes
C25 . F2 . 1.344(5) yes
C26 . C27 . 1.354(6) yes
C26 . H261 . 0.929 no
C27 . C28 . 1.381(5) yes
C27 . H271 . 0.934 no
C28 . H281 . 0.933 no
C29 . H291 . 0.950 no
C29 . H294 . 0.944 no
C29 . H295 . 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
N1 . Ni1 . N4 . 76.02(11) yes
N1 . Ni1 . N5 . 154.60(10) yes
N4 . Ni1 . N5 . 78.58(11) yes
N1 . Ni1 . N6 . 94.24(9) yes
N4 . Ni1 . N6 . 105.70(10) yes
N5 . Ni1 . N6 . 92.27(10) yes
N1 . Ni1 . N9 . 109.24(10) yes
N4 . Ni1 . N9 . 174.37(11) yes
N5 . Ni1 . N9 . 96.16(11) yes
N6 . Ni1 . N9 . 76.31(10) yes
N1 . Ni1 . N10 . 90.80(11) yes
N4 . Ni1 . N10 . 100.21(11) yes
N5 . Ni1 . N10 . 94.00(10) yes
N6 . Ni1 . N10 . 154.06(10) yes
N9 . Ni1 . N10 . 78.01(11) yes
Ni1 . N1 . C1 . 130.6(2) yes
Ni1 . N1 . C8 . 110.9(2) yes
C1 . N1 . C8 . 118.1(3) yes
C1 . N2 . C2 . 121.3(3) yes
C1 . N2 . H21 . 119.6 no
C2 . N2 . H21 . 119.1 no
N4 . N3 . C8 . 110.2(2) yes
N3 . N4 . Ni1 . 121.55(19) yes
N3 . N4 . C9 . 119.8(3) yes
Ni1 . N4 . C9 . 118.6(2) yes
Ni1 . N5 . C10 . 110.5(2) yes
Ni1 . N5 . C14 . 129.8(2) yes
C10 . N5 . C14 . 119.7(3) yes
Ni1 . N6 . C15 . 130.3(2) yes
Ni1 . N6 . C22 . 110.52(18) yes
C15 . N6 . C22 . 119.2(2) yes
C15 . N7 . C16 . 120.3(3) yes
C15 . N7 . H71 . 119.4 no
C16 . N7 . H71 . 120.3 no
N9 . N8 . C22 . 110.4(2) yes
N8 . N9 . Ni1 . 120.80(18) yes
N8 . N9 . C23 . 119.5(2) yes
Ni1 . N9 . C23 . 119.3(2) yes
Ni1 . N10 . C24 . 110.5(2) yes
Ni1 . N10 . C28 . 129.8(3) yes
C24 . N10 . C28 . 119.7(3) yes
O1 . N11 . O2 . 130.7(6) yes
O1 . N11 . O3 . 111.1(5) yes
O2 . N11 . O3 . 117.1(5) yes
O5 5_656 N12 . O4 . 117.5(2) yes
O5 5_656 N12 . O5 . 124.9(4) yes
O4 . N12 . O5 . 117.5(2) yes
O6 2_566 N13 . O7 2_566 119.5(5) yes
O6 2_566 N13 . O8 2_566 111.8(5) yes
O7 2_566 N13 . O8 2_566 121.2(5) yes
O6 2_566 N13 . O6 . 179.991 yes
O7 2_566 N13 . O6 . 60.5(5) yes
O8 2_566 N13 . O6 . 68.2(5) yes
O6 2_566 N13 . O7 . 60.5(5) yes
O7 2_566 N13 . O7 . 179.990 yes
O8 2_566 N13 . O7 . 58.8(5) yes
O6 . N13 . O7 . 119.5(5) yes
O6 2_566 N13 . O8 . 68.2(5) yes
O7 2_566 N13 . O8 . 58.8(5) yes
O8 2_566 N13 . O8 . 179.990 yes
O6 . N13 . O8 . 111.8(5) yes
O7 . N13 . O8 . 121.2(5) yes
H92 . O9 . H296 . 109.5 no
C29 . O10 . H103 . 123.8 no
N1 . C1 . N2 . 125.2(3) yes
N1 . C1 . H11 . 116.6 no
N2 . C1 . H11 . 118.2 no
N2 . C2 . C3 . 122.2(3) yes
N2 . C2 . C7 . 118.5(3) yes
C3 . C2 . C7 . 119.3(3) yes
C2 . C3 . C4 . 119.3(4) yes
C2 . C3 . H31 . 119.3 no
C4 . C3 . H31 . 121.3 no
C3 . C4 . C5 . 121.5(4) yes
C3 . C4 . H41 . 119.2 no
C5 . C4 . H41 . 119.3 no
C4 . C5 . C6 . 120.2(4) yes
C4 . C5 . H51 . 120.3 no
C6 . C5 . H51 . 119.4 no
C5 . C6 . C7 . 120.2(3) yes
C5 . C6 . H61 . 119.9 no
C7 . C6 . H61 . 119.8 no
C2 . C7 . C6 . 119.5(3) yes
C2 . C7 . C8 . 117.1(3) yes
C6 . C7 . C8 . 123.5(3) yes
C7 . C8 . N1 . 119.8(3) yes
C7 . C8 . N3 . 118.9(3) yes
N1 . C8 . N3 . 121.3(3) yes
N4 . C9 . C10 . 115.9(3) yes
N4 . C9 . H91 . 122.4 no
C10 . C9 . H91 . 121.7 no
C9 . C10 . N5 . 116.4(3) yes
C9 . C10 . C11 . 124.2(3) yes
N5 . C10 . C11 . 119.4(3) yes
C10 . C11 . C12 . 121.4(4) yes
C10 . C11 . F1 . 118.2(4) yes
C12 . C11 . F1 . 120.4(4) yes
C11 . C12 . C13 . 118.0(4) yes
C11 . C12 . H121 . 120.5 no
C13 . C12 . H121 . 121.5 no
C12 . C13 . C14 . 120.1(4) yes
C12 . C13 . H131 . 119.9 no
C14 . C13 . H131 . 120.0 no
C13 . C14 . N5 . 121.3(4) yes
C13 . C14 . H141 . 119.5 no
N5 . C14 . H141 . 119.2 no
N7 . C15 . N6 . 124.5(3) yes
N7 . C15 . H151 . 117.1 no
N6 . C15 . H151 . 118.4 no
N7 . C16 . C17 . 120.9(3) yes
N7 . C16 . C21 . 118.8(3) yes
C17 . C16 . C21 . 120.3(3) yes
C16 . C17 . C18 . 119.1(3) yes
C16 . C17 . H171 . 119.8 no
C18 . C17 . H171 . 121.0 no
C17 . C18 . C19 . 121.7(3) yes
C17 . C18 . H181 . 119.0 no
C19 . C18 . H181 . 119.3 no
C18 . C19 . C20 . 119.6(3) yes
C18 . C19 . H191 . 120.4 no
C20 . C19 . H191 . 120.0 no
C19 . C20 . C21 . 120.6(3) yes
C19 . C20 . H201 . 119.3 no
C21 . C20 . H201 . 120.1 no
C20 . C21 . C16 . 118.6(3) yes
C20 . C21 . C22 . 122.9(3) yes
C16 . C21 . C22 . 118.5(3) yes
C21 . C22 . N6 . 118.5(3) yes
C21 . C22 . N8 . 120.0(2) yes
N6 . C22 . N8 . 121.5(2) yes
N9 . C23 . C24 . 115.0(3) yes
N9 . C23 . H231 . 122.9 no
C24 . C23 . H231 . 122.2 no
C23 . C24 . N10 . 117.0(3) yes
C23 . C24 . C25 . 123.4(3) yes
N10 . C24 . C25 . 119.6(3) yes
C24 . C25 . C26 . 120.5(4) yes
C24 . C25 . F2 . 117.9(3) yes
C26 . C25 . F2 . 121.6(4) yes
C25 . C26 . C27 . 118.4(4) yes
C25 . C26 . H261 . 120.7 no
C27 . C26 . H261 . 120.9 no
C26 . C27 . C28 . 119.3(4) yes
C26 . C27 . H271 . 120.2 no
C28 . C27 . H271 . 120.4 no
C27 . C28 . N10 . 122.4(4) yes
C27 . C28 . H281 . 119.0 no
N10 . C28 . H281 . 118.6 no
O10 . C29 . H291 . 109.6 no
O10 . C29 . H294 . 109.6 no
H291 . C29 . H294 . 109.4 no
O10 . C29 . H295 . 109.3 no
H291 . C29 . H295 . 109.5 no
H294 . C29 . H295 . 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
N2 . H21 . O9 4_556 150 0.87 2.04 2.827(6) yes
N7 . H71 . O1 5_656 159 0.85 2.21 3.019(6) yes
N7 . H71 . O3 5_656 145 0.85 2.20 2.945(6) yes
C9 . H91 . O1 . 132 0.93 2.48 3.180(6) yes
O9 . H92 . O7 2_566 127 0.82 2.06 2.636(6) yes
O10 . H103 . N11 7_556 152 0.85 2.20 2.978(6) yes
O10 . H103 . O3 7_556 175 0.85 1.76 2.612(6) yes
C12 . H121 . O3 7_556 140 0.93 2.47 3.241(6) yes
C13 . H131 . C29 . 134 0.92 2.59 3.291(6) yes
C19 . H191 . O5 2_666 131 0.93 2.44 3.128(6) yes
O10 4_566 H294 . O10 . 142 0.86 1.73 2.464(6) yes
O10 4_566 H294 . C29 . 132 0.86 0.94 1.642(6) 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
3 1 0 x .
0 0 6 x .
-2 2 4 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
