# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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 2474866'
loop_
_audit_author_name
_audit_author_address
'Blanka Klepetarova'
;Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague 
Czech Republic
;
_audit_update_record             
;
2025-07-22 deposited with the CCDC.	2025-11-10 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. 
;


#--------------------------------------------------------------- 
# _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                   7.1432(4)
_cell_length_b                   8.2660(5)
_cell_length_c                   8.5093(5)
_cell_angle_alpha                84.334(3)
_cell_angle_beta                 77.131(3)
_cell_angle_gamma                68.244(2)
_cell_volume                     454.86(5)
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_chemical_absolute_configuration ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cu -1.9646 0.5888 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            1
_chemical_name_systematic        
1,1',3,3',5,5'-hexamethyl-4,4'-bis(trifluoromethyl)-[1,1'-bi(cyclohexane)]-2,2',5,5'-tetraene
_chemical_formula_moiety         'C20 H24 F6'

# Given Formula = C10 H10 Cu1 F3 
# Dc =      1.83 Fooo =    252.00 Mu =     34.60 M =    250.73
# Found Formula = C10 H12 F3 
# Dc =      1.38 FOOO =    198.00 Mu =     10.56 M =    189.20

_chemical_formula_sum            'C20 H24 F6'
_chemical_compound_source        .
_chemical_formula_weight         378.39


_cell_measurement_reflns_used    9400
_cell_measurement_theta_min      5.3331
_cell_measurement_theta_max      68.3747
_cell_measurement_temperature    180

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      180
_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.064

_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             198
_exptl_absorpt_coefficient_mu    1.056

# Sheldrick geometric approximatio 1.00 1.00 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_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_reflns_number            12479
_diffrn_reflns_av_unetI/netI     0.051
_reflns_number_total             1663
_diffrn_reflns_av_R_equivalents  0.040
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1663 
# Theoretical number of reflections is about 3341 


_diffrn_reflns_theta_min         5.333
_diffrn_reflns_theta_max         68.370
_diffrn_measured_fraction_theta_max 0.995

_diffrn_reflns_theta_full        68.370
_diffrn_measured_fraction_theta_full 0.995


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

_oxford_diffrn_Wilson_B_factor   3.80
_oxford_diffrn_Wilson_scale      14.93

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

_refine_diff_density_min         -0.22
_refine_diff_density_max         0.23


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

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1663
_refine_ls_R_factor_ref          0.0472
_refine_ls_wR_factor_ref         0.1263
_refine_ls_goodness_of_fit_ref   0.9755
_refine_ls_shift/su_max          0.0004128
_refine_ls_shift/su_mean         0.0000406


# Computed with I/sigma = -10 
_reflns_number_all               1663
_refine_ls_R_factor_all          0.0472
_refine_ls_wR_factor_all         0.1263

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1448
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_gt          0.1193


_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= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.08P)² + 0.16P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

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

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
F1 F 0.64695(18) 0.72451(15) 0.12424(14) 0.0615 1.0000 Uani . . . . . .
C2 C 0.7877(3) 0.6669(2) 0.2180(2) 0.0455 1.0000 Uani . . . . . .
F3 F 0.68184(17) 0.67872(16) 0.36973(13) 0.0609 1.0000 Uani . . . . . .
F4 F 0.88364(18) 0.49585(14) 0.18860(15) 0.0622 1.0000 Uani . . . . . .
C5 C 0.9353(2) 0.7659(2) 0.18740(17) 0.0378 1.0000 Uani . . . . . .
C6 C 0.8182(2) 0.9588(2) 0.21679(17) 0.0361 1.0000 Uani . . . . . .
C7 C 0.8251(2) 1.0325(2) 0.34605(18) 0.0356 1.0000 Uani . . . . . .
C8 C 0.9424(2) 0.94175(19) 0.47702(17) 0.0351 1.0000 Uani . . . . . .
C9 C 0.7898(2) 0.9154(2) 0.62782(19) 0.0408 1.0000 Uani . . . . . .
C10 C 1.0974(2) 0.7681(2) 0.41487(18) 0.0369 1.0000 Uani . . . . . .
C11 C 1.1014(2) 0.6881(2) 0.28584(18) 0.0372 1.0000 Uani . . . . . .
C12 C 1.2748(3) 0.5221(2) 0.2272(2) 0.0466 1.0000 Uani . . . . . .
C13 C 0.6990(3) 1.0643(2) 0.09308(19) 0.0427 1.0000 Uani . . . . . .
H51 H 0.9979 0.7525 0.0752 0.0434 1.0000 Uiso R . . . . .
H71 H 0.7525 1.1532 0.3546 0.0402 1.0000 Uiso R . . . . .
H91 H 0.8609 0.8497 0.7099 0.0584 1.0000 Uiso R . . . . .
H93 H 0.6927 1.0277 0.6727 0.0590 1.0000 Uiso R . . . . .
H92 H 0.7109 0.8534 0.5980 0.0588 1.0000 Uiso R . . . . .
H101 H 1.2053 0.7114 0.4737 0.0425 1.0000 Uiso R . . . . .
H123 H 1.3745 0.4862 0.2942 0.0662 1.0000 Uiso R . . . . .
H122 H 1.3416 0.5404 0.1178 0.0672 1.0000 Uiso R . . . . .
H121 H 1.2247 0.4288 0.2279 0.0670 1.0000 Uiso R . . . . .
H133 H 0.6644 1.1859 0.1084 0.0619 1.0000 Uiso R . . . . .
H132 H 0.7815 1.0433 -0.0102 0.0630 1.0000 Uiso R . . . . .
H131 H 0.5778 1.0410 0.0925 0.0630 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0652(7) 0.0672(7) 0.0705(7) -0.0018(6) -0.0333(6) -0.0333(6)
C2 0.0492(9) 0.0477(9) 0.0445(9) -0.0080(7) -0.0115(7) -0.0201(8)
F3 0.0637(7) 0.0783(8) 0.0512(6) -0.0071(5) 0.0004(5) -0.0428(6)
F4 0.0662(7) 0.0456(6) 0.0827(8) -0.0137(5) -0.0179(6) -0.0242(5)
C5 0.0415(8) 0.0442(9) 0.0290(7) -0.0091(6) -0.0042(6) -0.0162(7)
C6 0.0353(7) 0.0436(8) 0.0307(7) -0.0041(6) -0.0055(6) -0.0154(6)
C7 0.0344(7) 0.0368(8) 0.0341(8) -0.0063(6) -0.0063(6) -0.0101(6)
C8 0.0372(8) 0.0371(8) 0.0313(7) -0.0060(6) -0.0079(6) -0.0118(6)
C9 0.0434(8) 0.0452(9) 0.0351(8) -0.0045(6) -0.0054(6) -0.0179(7)
C10 0.0382(8) 0.0376(8) 0.0353(8) -0.0041(6) -0.0095(6) -0.0118(6)
C11 0.0386(8) 0.0367(8) 0.0354(8) -0.0052(6) -0.0034(6) -0.0135(6)
C12 0.0481(9) 0.0398(9) 0.0480(9) -0.0128(7) -0.0073(7) -0.0098(7)
C13 0.0452(9) 0.0509(9) 0.0335(8) -0.0023(7) -0.0112(7) -0.0167(7)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.5090(18)
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
F1 . C2 . 1.342(2) yes
C2 . F3 . 1.335(2) yes
C2 . F4 . 1.345(2) yes
C2 . C5 . 1.524(2) yes
C5 . C6 . 1.517(2) yes
C5 . C11 . 1.514(2) yes
C5 . H51 . 0.958 no
C6 . C7 . 1.328(2) yes
C6 . C13 . 1.504(2) yes
C7 . C8 . 1.514(2) yes
C7 . H71 . 0.940 no
C8 . C8 2_776 1.601(3) yes
C8 . C9 . 1.543(2) yes
C8 . C10 . 1.509(2) yes
C9 . H91 . 0.958 no
C9 . H93 . 0.982 no
C9 . H92 . 0.974 no
C10 . C11 . 1.326(2) yes
C10 . H101 . 0.960 no
C11 . C12 . 1.506(2) yes
C12 . H123 . 0.955 no
C12 . H122 . 0.972 no
C12 . H121 . 0.962 no
C13 . H133 . 0.957 no
C13 . H132 . 0.935 no
C13 . H131 . 0.955 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
F1 . C2 . F3 . 106.04(14) yes
F1 . C2 . F4 . 105.43(13) yes
F3 . C2 . F4 . 106.22(14) yes
F1 . C2 . C5 . 112.63(14) yes
F3 . C2 . C5 . 113.04(13) yes
F4 . C2 . C5 . 112.86(14) yes
C2 . C5 . C6 . 110.60(13) yes
C2 . C5 . C11 . 111.00(13) yes
C6 . C5 . C11 . 112.55(12) yes
C2 . C5 . H51 . 105.8 no
C6 . C5 . H51 . 107.7 no
C11 . C5 . H51 . 108.9 no
C5 . C6 . C7 . 120.84(14) yes
C5 . C6 . C13 . 118.00(13) yes
C7 . C6 . C13 . 121.15(14) yes
C6 . C7 . C8 . 126.24(14) yes
C6 . C7 . H71 . 116.2 no
C8 . C7 . H71 . 117.6 no
C7 . C8 . C8 2_776 109.96(15) yes
C7 . C8 . C9 . 109.14(12) yes
C8 2_776 C8 . C9 . 109.06(14) yes
C7 . C8 . C10 . 108.34(12) yes
C8 2_776 C8 . C10 . 110.03(14) yes
C9 . C8 . C10 . 110.31(12) yes
C8 . C9 . H91 . 111.1 no
C8 . C9 . H93 . 111.1 no
H91 . C9 . H93 . 108.4 no
C8 . C9 . H92 . 109.2 no
H91 . C9 . H92 . 109.1 no
H93 . C9 . H92 . 108.0 no
C8 . C10 . C11 . 126.51(14) yes
C8 . C10 . H101 . 116.4 no
C11 . C10 . H101 . 117.1 no
C5 . C11 . C10 . 120.80(14) yes
C5 . C11 . C12 . 117.51(13) yes
C10 . C11 . C12 . 121.63(14) yes
C11 . C12 . H123 . 111.3 no
C11 . C12 . H122 . 109.3 no
H123 . C12 . H122 . 108.9 no
C11 . C12 . H121 . 110.9 no
H123 . C12 . H121 . 107.4 no
H122 . C12 . H121 . 109.0 no
C6 . C13 . H133 . 110.0 no
C6 . C13 . H132 . 110.3 no
H133 . C13 . H132 . 104.5 no
C6 . C13 . H131 . 113.7 no
H133 . C13 . H131 . 110.0 no
H132 . C13 . H131 . 107.8 no


_iucr_refine_instructions_details 
;
#
# Punched on 21/10/24 at 14:43:32
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  93,X'S) H   (  92,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 123,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 133,X'S) H   ( 132,X'S) H   ( 131,X'S) 
END                                                                             
#
# Punched on 21/10/24 at 14:43:32
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

_refine_special_details          
;
?
  Reflections are selected by the following conditions :-
  Minimum value of SQRTW        is   0.00
  Minimum value of RATIO        is  -3.00
;

####################################################################### 
# 
# 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 2474867'
loop_
_audit_author_name
_audit_author_address
'Blanka Klepetarova'
;Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague 
Czech Republic
;
_audit_update_record             
;
2025-07-22 deposited with the CCDC.	2025-11-10 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. 
;


#--------------------------------------------------------------- 
# _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                   9.6718(2)
_cell_length_b                   7.81519(14)
_cell_length_c                   15.5844(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.285(2)
_cell_angle_gamma                90
_cell_volume                     1165.68(4)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4
_chemical_name_systematic        
3-methyl-7-propyl-8-(trifluoromethyl)-3,7-dihydro-1/H/-purine-2,6-dione
_chemical_formula_moiety         'C10 H11 F3 N4 O2'

# Given Formula = C7.50 H8.25 F2.25 N3 O1.50 
# Dc =      1.18 Fooo =    426.00 Mu =      9.52 M =    207.16
# Found Formula = C10 H11 F3 N4 O2 
# Dc =      1.57 FOOO =    568.00 Mu =     12.70 M =    276.22

_chemical_formula_sum            'C10 H11 F3 N4 O2'
_chemical_compound_source        .
_chemical_formula_weight         276.22


_cell_measurement_reflns_used    3721
_cell_measurement_theta_min      4.5970
_cell_measurement_theta_max      76.7490
_cell_measurement_temperature    100

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      100
_exptl_crystal_size_min          0.027
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_max          0.105

_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    1.270

# Sheldrick geometric approximatio 1.00 1.00 
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
; 
 Gaussian Integration (Busing and Levy, 1957) 
;
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ?

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_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_reflns_number            8456
_diffrn_reflns_av_unetI/netI     0.064
_reflns_number_total             2433
_diffrn_reflns_av_R_equivalents  0.040
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2433 
# Theoretical number of reflections is about 4987 


_diffrn_reflns_theta_min         4.620
_diffrn_reflns_theta_max         77.997
_diffrn_measured_fraction_theta_max 0.977

_diffrn_reflns_theta_full        74.097
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   1.51
_oxford_diffrn_Wilson_scale      0.09

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

_refine_diff_density_min         -0.42
_refine_diff_density_max         0.37


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

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2433
_refine_ls_R_factor_ref          0.0573
_refine_ls_wR_factor_ref         0.1326
_refine_ls_goodness_of_fit_ref   0.9849
_refine_ls_shift/su_max          0.0003907
_refine_ls_shift/su_mean         0.0000598


# Computed with I/sigma = -10 
_reflns_number_all               2433
_refine_ls_R_factor_all          0.0573
_refine_ls_wR_factor_all         0.1326

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1991
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_gt          0.1240


_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= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.09P)² + 0.41P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

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

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
F1 F 0.53394(12) 0.64018(14) 0.56869(8) 0.0238 1.0000 Uani . . . . . .
C2 C 0.6736(2) 0.6264(2) 0.58275(12) 0.0180 1.0000 Uani . . . . . .
F3 F 0.70656(13) 0.49655(13) 0.53305(8) 0.0247 1.0000 Uani . . . . . .
F4 F 0.71059(14) 0.58044(15) 0.66497(8) 0.0283 1.0000 Uani . . . . . .
C5 C 0.74377(18) 0.7903(2) 0.56387(11) 0.0151 1.0000 Uani . . . . . .
N6 N 0.73263(16) 0.86177(18) 0.48372(10) 0.0153 1.0000 Uani . . . . . .
C7 C 0.80664(19) 1.0134(2) 0.49596(11) 0.0147 1.0000 Uani . . . . . .
C8 C 0.85700(18) 1.0201(2) 0.58315(11) 0.0143 1.0000 Uani . . . . . .
N9 N 0.81737(16) 0.88089(18) 0.62593(10) 0.0151 1.0000 Uani . . . . . .
N10 N 0.93792(16) 1.15228(17) 0.62062(10) 0.0149 1.0000 Uani . . . . . .
C11 C 0.96792(19) 1.2860(2) 0.56901(12) 0.0154 1.0000 Uani . . . . . .
O12 O 1.03573(15) 1.41104(16) 0.59864(9) 0.0201 1.0000 Uani . . . . . .
N13 N 0.91806(16) 1.27358(18) 0.48133(10) 0.0156 1.0000 Uani . . . . . .
C14 C 0.83524(19) 1.1458(2) 0.43671(12) 0.0155 1.0000 Uani . . . . . .
O15 O 0.79675(15) 1.15305(16) 0.35891(9) 0.0207 1.0000 Uani . . . . . .
C16 C 0.9883(2) 1.1533(2) 0.71411(12) 0.0188 1.0000 Uani . . . . . .
C17 C 0.65196(19) 0.8042(2) 0.40112(11) 0.0173 1.0000 Uani . . . . . .
C18 C 0.5139(2) 0.9002(3) 0.37988(13) 0.0228 1.0000 Uani . . . . . .
C19 C 0.4342(2) 0.8420(3) 0.29394(13) 0.0257 1.0000 Uani . . . . . .
H163 H 1.0650 1.2332 0.7268 0.0286 1.0000 Uiso R . . . . .
H162 H 1.0217 1.0392 0.7310 0.0289 1.0000 Uiso R . . . . .
H161 H 0.9115 1.1817 0.7449 0.0292 1.0000 Uiso R . . . . .
H171 H 0.7106 0.8251 0.3570 0.0216 1.0000 Uiso R . . . . .
H172 H 0.6350 0.6803 0.4054 0.0216 1.0000 Uiso R . . . . .
H181 H 0.5343 1.0229 0.3767 0.0272 1.0000 Uiso R . . . . .
H182 H 0.4577 0.8773 0.4262 0.0282 1.0000 Uiso R . . . . .
H193 H 0.3504 0.9079 0.2805 0.0395 1.0000 Uiso R . . . . .
H192 H 0.4915 0.8597 0.2480 0.0398 1.0000 Uiso R . . . . .
H191 H 0.4117 0.7220 0.2947 0.0395 1.0000 Uiso R . . . . .
H131 H 0.9307 1.3640 0.4513 0.0207 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0158(6) 0.0220(5) 0.0340(7) -0.0025(5) 0.0051(4) -0.0040(4)
C2 0.0189(9) 0.0143(8) 0.0202(9) -0.0004(6) 0.0011(7) -0.0025(6)
F3 0.0262(6) 0.0130(5) 0.0355(7) -0.0043(4) 0.0058(5) -0.0007(4)
F4 0.0346(7) 0.0251(6) 0.0229(6) 0.0074(5) -0.0033(5) -0.0130(5)
C5 0.0151(8) 0.0128(7) 0.0174(8) -0.0014(6) 0.0025(6) -0.0012(6)
N6 0.0172(7) 0.0127(6) 0.0159(7) -0.0010(5) 0.0019(6) -0.0009(5)
C7 0.0145(8) 0.0132(7) 0.0163(8) -0.0017(6) 0.0024(6) -0.0022(6)
C8 0.0150(8) 0.0122(7) 0.0160(8) -0.0007(6) 0.0033(6) 0.0001(6)
N9 0.0152(7) 0.0128(6) 0.0171(7) 0.0005(5) 0.0016(5) -0.0015(5)
N10 0.0182(8) 0.0111(6) 0.0146(7) -0.0010(5) 0.0003(5) -0.0017(5)
C11 0.0167(8) 0.0117(7) 0.0179(8) 0.0005(6) 0.0030(6) 0.0009(6)
O12 0.0265(7) 0.0131(6) 0.0198(6) -0.0003(5) 0.0005(5) -0.0057(5)
N13 0.0202(8) 0.0116(6) 0.0149(7) 0.0005(5) 0.0023(6) -0.0015(5)
C14 0.0164(8) 0.0152(7) 0.0155(8) -0.0003(6) 0.0042(6) 0.0009(6)
O15 0.0258(7) 0.0217(6) 0.0140(6) 0.0002(5) 0.0012(5) -0.0025(5)
C16 0.0229(9) 0.0185(8) 0.0145(8) -0.0015(6) 0.0007(7) -0.0041(7)
C17 0.0178(9) 0.0171(8) 0.0162(8) -0.0029(6) -0.0004(6) -0.0016(6)
C18 0.0187(10) 0.0270(9) 0.0221(9) -0.0050(7) 0.0012(7) 0.0024(7)
C19 0.0214(10) 0.0330(10) 0.0214(9) -0.0038(8) -0.0011(7) 0.0001(8)

_refine_ls_extinction_coef       51(8)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          2.88(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 . C2 . 1.342(2) yes
C2 . F3 . 1.342(2) yes
C2 . F4 . 1.329(2) yes
C2 . C5 . 1.499(2) yes
C5 . N6 . 1.358(2) yes
C5 . N9 . 1.321(2) yes
N6 . C7 . 1.383(2) yes
N6 . C17 . 1.476(2) yes
C7 . C8 . 1.377(2) yes
C7 . C14 . 1.440(2) yes
C8 . N9 . 1.359(2) yes
C8 . N10 . 1.375(2) yes
N10 . C11 . 1.375(2) yes
N10 . C16 . 1.468(2) yes
C11 . O12 . 1.229(2) yes
C11 . N13 . 1.385(2) yes
N13 . C14 . 1.401(2) yes
N13 . H131 . 0.866 no
C14 . O15 . 1.217(2) yes
C16 . H163 . 0.968 no
C16 . H162 . 0.971 no
C16 . H161 . 0.966 no
C17 . C18 . 1.526(3) yes
C17 . H171 . 0.966 no
C17 . H172 . 0.986 no
C18 . C19 . 1.516(3) yes
C18 . H181 . 0.982 no
C18 . H182 . 0.981 no
C19 . H193 . 0.958 no
C19 . H192 . 0.977 no
C19 . H191 . 0.963 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
F1 . C2 . F3 . 106.47(14) yes
F1 . C2 . F4 . 107.68(15) yes
F3 . C2 . F4 . 107.39(15) yes
F1 . C2 . C5 . 111.89(14) yes
F3 . C2 . C5 . 112.42(15) yes
F4 . C2 . C5 . 110.72(15) yes
C2 . C5 . N6 . 123.62(16) yes
C2 . C5 . N9 . 121.72(16) yes
N6 . C5 . N9 . 114.60(15) yes
C5 . N6 . C7 . 104.73(14) yes
C5 . N6 . C17 . 129.69(15) yes
C7 . N6 . C17 . 125.42(15) yes
N6 . C7 . C8 . 105.74(15) yes
N6 . C7 . C14 . 132.10(16) yes
C8 . C7 . C14 . 122.16(15) yes
C7 . C8 . N9 . 111.65(15) yes
C7 . C8 . N10 . 123.14(16) yes
N9 . C8 . N10 . 125.21(16) yes
C8 . N9 . C5 . 103.29(15) yes
C8 . N10 . C11 . 118.56(15) yes
C8 . N10 . C16 . 120.85(14) yes
C11 . N10 . C16 . 120.57(14) yes
N10 . C11 . O12 . 122.05(16) yes
N10 . C11 . N13 . 116.80(15) yes
O12 . C11 . N13 . 121.15(16) yes
C11 . N13 . C14 . 129.23(15) yes
C11 . N13 . H131 . 114.8 no
C14 . N13 . H131 . 115.4 no
C7 . C14 . N13 . 110.06(15) yes
C7 . C14 . O15 . 127.80(16) yes
N13 . C14 . O15 . 122.14(16) yes
N10 . C16 . H163 . 109.9 no
N10 . C16 . H162 . 108.3 no
H163 . C16 . H162 . 108.8 no
N10 . C16 . H161 . 108.9 no
H163 . C16 . H161 . 111.8 no
H162 . C16 . H161 . 109.0 no
N6 . C17 . C18 . 112.03(15) yes
N6 . C17 . H171 . 106.2 no
C18 . C17 . H171 . 110.3 no
N6 . C17 . H172 . 108.2 no
C18 . C17 . H172 . 110.4 no
H171 . C17 . H172 . 109.6 no
C17 . C18 . C19 . 111.20(16) yes
C17 . C18 . H181 . 108.4 no
C19 . C18 . H181 . 109.2 no
C17 . C18 . H182 . 108.1 no
C19 . C18 . H182 . 109.3 no
H181 . C18 . H182 . 110.6 no
C18 . C19 . H193 . 109.8 no
C18 . C19 . H192 . 109.6 no
H193 . C19 . H192 . 108.4 no
C18 . C19 . H191 . 111.6 no
H193 . C19 . H191 . 109.9 no
H192 . C19 . H191 . 107.5 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
C16 . H161 . O15 3_575 154 0.97 2.57 3.467(3) yes
N13 . H131 . O12 2_786 171 0.87 1.97 2.826(3) yes


_iucr_refine_instructions_details 
;
#
# Punched on 31/01/25 at 15:25:42
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
CONT EXTPARAM 
RIDE N   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  16,X'S) H   ( 163,X'S) H   ( 162,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  19,X'S) H   ( 193,X'S) H   ( 192,X'S) H   ( 191,X'S) 
END                                                                             
#
# Punched on 31/01/25 at 15:25:42
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

_refine_special_details          
;
?
  Reflections are selected by the following conditions :-
  Minimum value of SQRTW        is   0.00
  Minimum value of RATIO        is  -3.00
;

####################################################################### 
# 
# 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 2474868'
loop_
_audit_author_name
_audit_author_address
'Blanka Klepetarova'
;Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague 
Czech Republic
;
_audit_update_record             
;
2025-07-22 deposited with the CCDC.	2025-11-10 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. 
;


#--------------------------------------------------------------- 
# _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                   6.35117(16)
_cell_length_b                   12.2470(3)
_cell_length_c                   9.1130(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.270(3)
_cell_angle_gamma                90
_cell_volume                     680.44(3)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cu -1.9646 0.5888 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'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2
_chemical_name_systematic        'ammonium copper(II) sulfate hexahydrate'
_chemical_formula_moiety         'Cu H12 O6, 2(O4 S), 2(H4 N)'

# Given Formula = C5.50 H3.50 Cu2 N2.50 O0.50 S2 
# Dc =      2.97 Fooo =    592.00 Mu =    129.10 M =    303.83
# Found Formula = H10 Cu0.50 N1 O7 S1 
# Dc =      1.95 FOOO =    414.00 Mu =     58.86 M =    199.92

_chemical_formula_sum            'Cu H20 N2 O14 S2'
_chemical_compound_source        .
_chemical_formula_weight         399.85


_cell_measurement_reflns_used    7043
_cell_measurement_theta_min      3.5980
_cell_measurement_theta_max      78.1270
_cell_measurement_temperature    100

_exptl_crystal_description       plate
_exptl_crystal_colour            'light blue'

_diffrn_ambient_temperature      100
_exptl_crystal_size_min          0.091
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_max          0.345

_exptl_crystal_density_diffrn    1.951
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             414
_exptl_absorpt_coefficient_mu    5.886

# Sheldrick geometric approximatio 1.00 1.00 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ?

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_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_reflns_number            9577
_diffrn_reflns_av_unetI/netI     0.055
_reflns_number_total             1435
_diffrn_reflns_av_R_equivalents  0.046
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1435 
# Theoretical number of reflections is about 2922 


_diffrn_reflns_theta_min         6.217
_diffrn_reflns_theta_max         78.341
_diffrn_measured_fraction_theta_max 0.982

_diffrn_reflns_theta_full        75.990
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              11

_oxford_diffrn_Wilson_B_factor   1.05
_oxford_diffrn_Wilson_scale      0.05

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

_refine_diff_density_min         -0.56
_refine_diff_density_max         0.45


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

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     88
_refine_ls_number_reflns         1435
_refine_ls_R_factor_ref          0.0280
_refine_ls_wR_factor_ref         0.0741
_refine_ls_goodness_of_fit_ref   0.9991
_refine_ls_shift/su_max          0.0006852
_refine_ls_shift/su_mean         0.0000599


# Computed with I/sigma = -10 
_reflns_number_all               1435
_refine_ls_R_factor_all          0.0280
_refine_ls_wR_factor_all         0.0741

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1364
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_gt          0.0733


_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= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.88P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

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

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cu1 Cu 0.5000 1.0000 0.5000 0.0084 1.0000 Uani S . . . . .
O2 O 0.7823(2) 0.93563(11) 0.49356(15) 0.0115 1.0000 Uani . . . . . .
O3 O 0.4711(2) 0.89114(11) 0.65742(14) 0.0114 1.0000 Uani . . . . . .
O4 O 0.6779(2) 1.11859(11) 0.68615(15) 0.0125 1.0000 Uani . . . . . .
S5 S 0.75582(7) 0.63504(3) 0.58041(5) 0.0084 1.0000 Uani . . . . . .
O6 O 0.8671(2) 0.56808(10) 0.71557(14) 0.0114 1.0000 Uani . . . . . .
O7 O 0.7157(2) 0.56794(11) 0.44218(15) 0.0148 1.0000 Uani . . . . . .
O8 O 0.5477(2) 0.67948(11) 0.59877(15) 0.0124 1.0000 Uani . . . . . .
O9 O 0.9032(2) 0.72786(11) 0.57073(15) 0.0120 1.0000 Uani . . . . . .
N10 N 1.1422(3) 0.84214(13) 0.85850(18) 0.0125 1.0000 Uani . . . . . .
H21 H 0.8049 0.8709 0.5140 0.0172 1.0000 Uiso R . . . . .
H22 H 0.8082 0.9397 0.4120 0.0181 1.0000 Uiso R . . . . .
H31 H 0.5427 0.9046 0.7439 0.0183 1.0000 Uiso R . . . . .
H42 H 0.8019 1.0988 0.7240 0.0196 1.0000 Uiso R . . . . .
H41 H 0.6271 1.1239 0.7578 0.0193 1.0000 Uiso R . . . . .
H32 H 0.4947 0.8295 0.6349 0.0181 1.0000 Uiso R . . . . .
H103 H 1.1276 0.9113 0.8323 0.0189 1.0000 Uiso R . . . . .
H104 H 1.2804 0.8303 0.9094 0.0193 1.0000 Uiso R . . . . .
H101 H 1.1063 0.8009 0.7761 0.0198 1.0000 Uiso R . . . . .
H102 H 1.0571 0.8269 0.9178 0.0193 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0098(2) 0.0070(2) 0.0080(2) 0.00073(12) 0.00201(15) 0.00100(13)
O2 0.0141(7) 0.0095(6) 0.0117(6) 0.0016(5) 0.0050(5) 0.0019(5)
O3 0.0155(7) 0.0092(6) 0.0087(6) -0.0001(5) 0.0020(5) 0.0007(5)
O4 0.0123(7) 0.0130(6) 0.0117(6) -0.0010(5) 0.0024(5) 0.0005(5)
S5 0.0101(2) 0.0068(2) 0.0078(2) 0.00024(14) 0.00144(16) 0.00027(14)
O6 0.0134(7) 0.0104(7) 0.0095(6) 0.0023(5) 0.0015(5) 0.0016(5)
O7 0.0200(7) 0.0135(7) 0.0092(6) -0.0022(5) 0.0010(5) 0.0007(5)
O8 0.0104(6) 0.0106(6) 0.0162(7) 0.0008(5) 0.0038(5) 0.0009(5)
O9 0.0118(6) 0.0090(6) 0.0149(7) 0.0022(5) 0.0033(5) -0.0017(5)
N10 0.0130(8) 0.0108(8) 0.0135(8) -0.0003(6) 0.0034(6) -0.0001(6)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.40(18)
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 . O4 2_676 2.2781(13) yes
Cu1 . O3 2_676 2.0042(13) yes
Cu1 . O2 2_676 1.9747(13) yes
Cu1 . O2 . 1.9747(13) yes
Cu1 . O3 . 2.0042(13) yes
Cu1 . O4 . 2.2781(13) yes
O2 . H21 . 0.818 no
O2 . H22 . 0.806 no
O3 . H31 . 0.809 no
O3 . H32 . 0.807 no
O4 . H42 . 0.803 no
O4 . H41 . 0.808 no
S5 . O6 . 1.4837(13) yes
S5 . O7 . 1.4653(13) yes
S5 . O8 . 1.4819(14) yes
S5 . O9 . 1.4908(13) yes
N10 . H103 . 0.878 no
N10 . H104 . 0.883 no
N10 . H101 . 0.881 no
N10 . H102 . 0.884 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
O4 2_676 Cu1 . O3 2_676 90.97(5) yes
O4 2_676 Cu1 . O2 2_676 90.66(5) yes
O3 2_676 Cu1 . O2 2_676 91.25(5) yes
O4 2_676 Cu1 . O2 . 89.34(5) yes
O3 2_676 Cu1 . O2 . 88.75(5) yes
O2 2_676 Cu1 . O2 . 179.99 yes
O4 2_676 Cu1 . O3 . 89.03(5) yes
O3 2_676 Cu1 . O3 . 179.99 yes
O2 2_676 Cu1 . O3 . 88.75(5) yes
O2 . Cu1 . O3 . 91.25(5) yes
O4 2_676 Cu1 . O4 . 179.99 yes
O3 2_676 Cu1 . O4 . 89.03(5) yes
O2 2_676 Cu1 . O4 . 89.34(5) yes
O2 . Cu1 . O4 . 90.66(5) yes
O3 . Cu1 . O4 . 90.97(5) yes
Cu1 . O2 . H21 . 118.9 no
Cu1 . O2 . H22 . 115.1 no
H21 . O2 . H22 . 101.6 no
Cu1 . O3 . H31 . 115.0 no
Cu1 . O3 . H32 . 112.3 no
H31 . O3 . H32 . 110.1 no
Cu1 . O4 . H42 . 110.4 no
Cu1 . O4 . H41 . 115.2 no
H42 . O4 . H41 . 104.1 no
O6 . S5 . O7 . 109.35(8) yes
O6 . S5 . O8 . 109.98(8) yes
O7 . S5 . O8 . 110.93(8) yes
O6 . S5 . O9 . 108.04(8) yes
O7 . S5 . O9 . 109.73(8) yes
O8 . S5 . O9 . 108.76(8) yes
H103 . N10 . H104 . 108.4 no
H103 . N10 . H101 . 109.9 no
H104 . N10 . H101 . 109.6 no
H103 . N10 . H102 . 109.5 no
H104 . N10 . H102 . 109.4 no
H101 . N10 . H102 . 110.1 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O2 . H21 . O9 . 171 0.82 1.88 2.6938(19) yes
O2 . H22 . O6 3_564 174 0.81 1.93 2.7339(18) yes
O3 . H31 . O7 3_565 178 0.81 1.86 2.6720(18) yes
O4 . H42 . O6 4_756 168 0.80 2.05 2.8435(19) yes
O4 . H41 . O8 4_656 162 0.81 2.05 2.8327(19) yes
O3 . H32 . O8 . 175 0.81 1.91 2.7180(19) yes
N10 . H103 . O6 4_756 173 0.88 1.97 2.845(2) yes
N10 . H104 . O8 3_665 156 0.88 2.06 2.887(2) yes
N10 . H101 . O9 . 159 0.88 2.15 2.985(2) yes
N10 . H102 . O7 3_565 128 0.88 2.58 3.208(2) yes
N10 . H102 . O9 3_565 170 0.88 2.03 2.903(2) yes


_iucr_refine_instructions_details 
;
#
# Punched on 15/07/25 at 15:44:16
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
RIDE O   (   2,X'S) H   (  21,X'S) H   (  22,X'S) 
RIDE O   (   3,X'S) H   (  31,X'S) H   (  32,X'S) 
RIDE O   (   4,X'S) H   (  42,X'S) H   (  41,X'S) 
REM TOO MANY H ATOMS ON N   (  10), - 4 
RIDE N   (  10,X'S) H   ( 103,X'S) H   ( 104,X'S) H   ( 101,X'S) H   ( 102,X'S) 
END                                                                             
#
# Punched on 15/07/25 at 15:44:16
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

_refine_special_details          
;
?
  Reflections are selected by the following conditions :-
  Minimum value of SQRTW        is   0.00
  Minimum value of RATIO        is  -3.00
;

