# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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 2382300'
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             
;
2024-09-06 deposited with the CCDC.	2024-11-18 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. 
;


#--------------------------------------------------------------- 
# _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                   4.6371(10)
_cell_length_b                   33.771(7)
_cell_length_c                   5.6015(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.286(6)
_cell_angle_gamma                90
_cell_volume                     871.9(3)
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'
_chemical_absolute_configuration .
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z
x,-y+1/2,z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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'
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2
_chemical_name_systematic        
bis(4-(4-bromophenyl)-1H-1,2,3-triazol-1-yl)difluoromethane
_chemical_formula_moiety         'C17 H10 Br2 F2 N6'

# Given Formula = C9 H5 Br2 F2 N3 
# Dc =      2.69 Fooo =    672.00 Mu =    118.94 M =    352.96
# Found Formula = C8.50 H5 Br1 F1 N3 
# Dc =      1.89 FOOO =    484.00 Mu =     62.32 M =    248.06

_chemical_formula_sum            'C17 H10 Br2 F2 N6'
_chemical_compound_source        .
_chemical_formula_weight         496.11


_cell_measurement_reflns_used    9132
_cell_measurement_theta_min      4.1640
_cell_measurement_theta_max      68.5155
_cell_measurement_temperature    180

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      180
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.149

_exptl_crystal_density_diffrn    1.890
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    6.232

# Sheldrick geometric approximatio 1.00 1.00 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_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       'Apex3 (Bruker AXS, 2015)'
_computing_cell_refinement       'Apex3 (Bruker AXS, 2015)'
_computing_data_reduction        'Apex3 (Bruker AXS, 2015)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .
_diffrn_reflns_number            12951
_diffrn_reflns_av_unetI/netI     0.177
_reflns_number_total             1637
_diffrn_reflns_av_R_equivalents  0.086
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1637 
# Theoretical number of reflections is about 3199 


_diffrn_reflns_theta_min         2.617
_diffrn_reflns_theta_max         68.327
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        68.327
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_reflns_limit_h_min              -5
_reflns_limit_h_max              5
_reflns_limit_k_min              0
_reflns_limit_k_max              40
_reflns_limit_l_min              0
_reflns_limit_l_max              6

_oxford_diffrn_Wilson_B_factor   3.36
_oxford_diffrn_Wilson_scale      63.35

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

_refine_diff_density_min         -0.69
_refine_diff_density_max         1.05


# 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     127
_refine_ls_number_reflns         1637
_refine_ls_R_factor_ref          0.0656
_refine_ls_wR_factor_ref         0.1600
_refine_ls_goodness_of_fit_ref   1.0839
_refine_ls_shift/su_max          0.0002963
_refine_ls_shift/su_mean         0.0000507


# Computed with I/sigma = -10 
_reflns_number_all               1637
_refine_ls_R_factor_all          0.0656
_refine_ls_wR_factor_all         0.1600

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1491
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_gt          0.1571


_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) + ( 0.00P)² + 8.07P] 
 ,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
Br1 Br 0.1656(2) 0.53320(2) 0.72354(16) 0.0516 1.0000 Uani . . . . . .
C2 C 0.4274(15) 0.57453(19) 0.8304(12) 0.0338 1.0000 Uani . . . . . .
C3 C 0.5684(17) 0.5732(2) 1.0605(12) 0.0398 1.0000 Uani . . . . . .
C4 C 0.7630(16) 0.6030(2) 1.1342(11) 0.0361 1.0000 Uani . . . . . .
C5 C 0.8148(15) 0.63386(18) 0.9809(10) 0.0301 1.0000 Uani . . . . . .
C6 C 1.0217(14) 0.66557(18) 1.0588(10) 0.0283 1.0000 Uani . . . . . .
N7 N 1.1140(14) 0.67174(16) 1.2975(9) 0.0369 1.0000 Uani . . . . . .
N8 N 1.2916(14) 0.70147(17) 1.3209(9) 0.0368 1.0000 Uani . . . . . .
N9 N 1.3217(12) 0.71434(15) 1.0944(9) 0.0290 1.0000 Uani . . . . . .
C10 C 1.1536(14) 0.69317(18) 0.9286(10) 0.0287 1.0000 Uani . . . . . .
C11 C 1.479(2) 0.7500 1.0628(15) 0.0325 1.0000 Uani S T . . . .
F12 F 1.7197(12) 0.7500 1.2175(10) 0.0392 1.0000 Uani S T . . . .
F13 F 1.5546(13) 0.7500 0.8388(9) 0.0385 1.0000 Uani S T . . . .
C14 C 0.6644(16) 0.6345(2) 0.7505(11) 0.0344 1.0000 Uani . . . . . .
C15 C 0.4735(17) 0.6047(2) 0.6764(12) 0.0399 1.0000 Uani . . . . . .
H31 H 0.5328 0.5526 1.1637 0.0481 1.0000 Uiso R . . . . .
H41 H 0.8625 0.6024 1.2877 0.0432 1.0000 Uiso R . . . . .
H101 H 1.1362 0.6965 0.7636 0.0352 1.0000 Uiso R . . . . .
H141 H 0.6936 0.6551 0.6465 0.0412 1.0000 Uiso R . . . . .
H151 H 0.3764 0.6050 0.5228 0.0479 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
Br1 0.0577(6) 0.0396(5) 0.0569(5) -0.0106(4) 0.0041(4) -0.0145(4)
C2 0.033(4) 0.030(3) 0.039(4) -0.009(3) 0.008(3) -0.004(3)
C3 0.055(5) 0.030(3) 0.035(3) 0.004(3) 0.009(3) -0.007(3)
C4 0.046(4) 0.036(4) 0.026(3) 0.005(3) 0.002(3) -0.002(3)
C5 0.041(4) 0.027(3) 0.023(3) -0.001(2) 0.006(3) -0.000(3)
C6 0.037(4) 0.028(3) 0.021(3) -0.000(2) 0.006(3) 0.004(3)
N7 0.056(4) 0.029(3) 0.025(3) 0.002(2) -0.001(2) -0.005(3)
N8 0.056(4) 0.036(3) 0.017(2) 0.004(2) 0.001(2) -0.001(3)
N9 0.038(3) 0.028(3) 0.021(2) 0.002(2) 0.003(2) 0.001(2)
C10 0.038(4) 0.031(3) 0.018(3) -0.003(2) 0.004(2) -0.001(3)
C11 0.036(5) 0.035(5) 0.025(4) 0.0000 -0.002(4) 0.0000
F12 0.036(3) 0.036(3) 0.043(3) 0.0000 -0.005(2) 0.0000
F13 0.049(3) 0.037(3) 0.032(3) 0.0000 0.014(2) 0.0000
C14 0.046(4) 0.032(3) 0.025(3) 0.004(3) 0.005(3) -0.000(3)
C15 0.059(5) 0.034(4) 0.026(3) -0.001(3) 0.000(3) -0.000(3)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1882(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . C2 . 1.903(6) yes
C2 . C3 . 1.381(10) yes
C2 . C15 . 1.367(10) yes
C3 . C4 . 1.385(10) yes
C3 . H31 . 0.929 no
C4 . C5 . 1.387(9) yes
C4 . H41 . 0.931 no
C5 . C6 . 1.472(9) yes
C5 . C14 . 1.398(9) yes
C6 . N7 . 1.375(8) yes
C6 . C10 . 1.369(9) yes
N7 . N8 . 1.296(8) yes
N8 . N9 . 1.362(7) yes
N9 . C10 . 1.351(8) yes
N9 . C11 . 1.430(7) yes
C10 . H101 . 0.926 no
C11 . F12 . 1.335(10) yes
C11 . F13 . 1.338(10) yes
C14 . C15 . 1.373(10) yes
C14 . H141 . 0.927 no
C15 . H151 . 0.927 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
Br1 . C2 . C3 . 119.3(5) yes
Br1 . C2 . C15 . 119.1(5) yes
C3 . C2 . C15 . 121.5(6) yes
C2 . C3 . C4 . 118.7(6) yes
C2 . C3 . H31 . 120.5 no
C4 . C3 . H31 . 120.8 no
C3 . C4 . C5 . 120.9(6) yes
C3 . C4 . H41 . 119.9 no
C5 . C4 . H41 . 119.2 no
C4 . C5 . C6 . 120.9(6) yes
C4 . C5 . C14 . 118.7(6) yes
C6 . C5 . C14 . 120.4(6) yes
C5 . C6 . N7 . 121.5(5) yes
C5 . C6 . C10 . 130.7(5) yes
N7 . C6 . C10 . 107.8(6) yes
C6 . N7 . N8 . 110.0(5) yes
N7 . N8 . N9 . 106.4(5) yes
N8 . N9 . C10 . 111.2(5) yes
N8 . N9 . C11 . 119.4(5) yes
C10 . N9 . C11 . 128.7(6) yes
C6 . C10 . N9 . 104.6(5) yes
C6 . C10 . H101 . 128.3 no
N9 . C10 . H101 . 127.1 no
N9 . C11 . N9 4_565 114.7(8) yes
N9 . C11 . F12 . 108.7(5) yes
N9 4_565 C11 . F12 . 108.7(5) yes
N9 . C11 . F13 . 107.8(5) yes
N9 4_565 C11 . F13 . 107.8(5) yes
F12 . C11 . F13 . 108.9(8) yes
C5 . C14 . C15 . 120.5(6) yes
C5 . C14 . H141 . 119.9 no
C15 . C14 . H141 . 119.6 no
C14 . C15 . C2 . 119.7(6) yes
C14 . C15 . H151 . 120.3 no
C2 . C15 . H151 . 120.0 no


_iucr_refine_instructions_details 
;
#
# Punched on 20/08/24 at 16:38:38
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
END                                                                             
#
# Punched on 20/08/24 at 16:38:38
#
#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 2382301'
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             
;
2024-09-06 deposited with the CCDC.	2024-11-18 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. 
;


#--------------------------------------------------------------- 
# _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                   13.7560(3)
_cell_length_b                   6.4533(2)
_cell_length_c                   16.5581(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.5808(7)
_cell_angle_gamma                90
_cell_volume                     1347.15(6)
_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 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4
_chemical_name_systematic        
1-fluoro-3-(4-phenyl-2H-1,2,3-triazol-2-yl)isoquinoline
_chemical_formula_moiety         'C17 H11 F N4'

# Given Formula = C17 H11 F1 N4 
# Dc =      1.43 Fooo =    600.00 Mu =      0.99 M =    290.30
# Found Formula = C17 H11 F1 N4 
# Dc =      1.43 FOOO =    600.00 Mu =      0.99 M =    290.30

_chemical_formula_sum            'C17 H11 F N4'
_chemical_compound_source        .
_chemical_formula_weight         290.30


_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.5191
_cell_measurement_theta_max      27.4284
_cell_measurement_temperature    180

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      180
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.037

_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.099

# Sheldrick geometric approximatio 1.00 1.00 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_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       'Apex3 (Bruker AXS, 2015)'
_computing_cell_refinement       'Apex3 (Bruker AXS, 2015)'
_computing_data_reduction        'Apex3 (Bruker AXS, 2015)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .
_diffrn_reflns_number            37999
_diffrn_reflns_av_unetI/netI     0.085
_reflns_number_total             3093
_diffrn_reflns_av_R_equivalents  0.057
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3093 
# Theoretical number of reflections is about 6180 


_diffrn_reflns_theta_min         1.615
_diffrn_reflns_theta_max         27.484
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        27.484
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -17
_reflns_limit_h_max              16
_reflns_limit_k_min              0
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              21

_oxford_diffrn_Wilson_B_factor   2.84
_oxford_diffrn_Wilson_scale      26.40

_atom_sites_solution_primary     direct #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         0.39


# 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     200
_refine_ls_number_reflns         3087
_refine_ls_R_factor_ref          0.0697
_refine_ls_wR_factor_ref         0.1429
_refine_ls_goodness_of_fit_ref   1.0381
_refine_ls_shift/su_max          0.0002244
_refine_ls_shift/su_mean         0.0000290


# Computed with I/sigma = -10 
_reflns_number_all               3093
_refine_ls_R_factor_all          0.0702
_refine_ls_wR_factor_all         0.1439

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2282
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_gt          0.1123


_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) + ( 0.05P)² + 1.18P] 
 ,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 0.23823(11) 1.1363(2) 0.41164(9) 0.0487 1.0000 Uani . . . . . .
C2 C 0.28238(17) 0.9977(3) 0.37563(13) 0.0349 1.0000 Uani . . . . . .
N3 N 0.22479(13) 0.8381(3) 0.34031(11) 0.0339 1.0000 Uani . . . . . .
C4 C 0.26984(15) 0.6972(3) 0.30475(12) 0.0305 1.0000 Uani . . . . . .
N5 N 0.20442(12) 0.5270(3) 0.26320(10) 0.0307 1.0000 Uani . . . . . .
N6 N 0.23160(13) 0.3931(3) 0.21378(10) 0.0312 1.0000 Uani . . . . . .
C7 C 0.15041(15) 0.2605(3) 0.18418(12) 0.0304 1.0000 Uani . . . . . .
C8 C 0.14475(15) 0.0893(3) 0.12442(12) 0.0301 1.0000 Uani . . . . . .
C9 C 0.08422(16) -0.0854(3) 0.12134(13) 0.0351 1.0000 Uani . . . . . .
C10 C 0.07723(17) -0.2453(3) 0.06371(14) 0.0393 1.0000 Uani . . . . . .
C11 C 0.12908(17) -0.2314(4) 0.00733(14) 0.0406 1.0000 Uani . . . . . .
C12 C 0.18770(17) -0.0568(4) 0.00873(14) 0.0410 1.0000 Uani . . . . . .
C13 C 0.19720(16) 0.1021(3) 0.06749(13) 0.0365 1.0000 Uani . . . . . .
C14 C 0.07567(17) 0.3223(3) 0.21815(14) 0.0366 1.0000 Uani . . . . . .
N15 N 0.11021(13) 0.4906(3) 0.26714(11) 0.0357 1.0000 Uani . . . . . .
C16 C 0.36954(16) 0.7131(3) 0.30653(13) 0.0333 1.0000 Uani . . . . . .
C17 C 0.43004(16) 0.8915(3) 0.34461(13) 0.0334 1.0000 Uani . . . . . .
C18 C 0.38490(16) 1.0435(3) 0.38096(12) 0.0334 1.0000 Uani . . . . . .
C19 C 0.44213(19) 1.2253(4) 0.41872(14) 0.0436 1.0000 Uani . . . . . .
C20 C 0.5415(2) 1.2528(4) 0.42050(16) 0.0485 1.0000 Uani . . . . . .
C21 C 0.58710(19) 1.1018(4) 0.38577(15) 0.0471 1.0000 Uani . . . . . .
C22 C 0.53341(17) 0.9251(4) 0.34863(14) 0.0415 1.0000 Uani . . . . . .
H91 H 0.0466 -0.0938 0.1584 0.0429 1.0000 Uiso R . . . . .
H101 H 0.0354 -0.3632 0.0611 0.0468 1.0000 Uiso R . . . . .
H111 H 0.1227 -0.3410 -0.0321 0.0493 1.0000 Uiso R . . . . .
H121 H 0.2234 -0.0452 -0.0307 0.0486 1.0000 Uiso R . . . . .
H131 H 0.2386 0.2213 0.0688 0.0441 1.0000 Uiso R . . . . .
H141 H 0.0097 0.2577 0.2084 0.0445 1.0000 Uiso R . . . . .
H161 H 0.3958 0.6055 0.2819 0.0391 1.0000 Uiso R . . . . .
H191 H 0.4117 1.3247 0.4426 0.0524 1.0000 Uiso R . . . . .
H201 H 0.5797 1.3742 0.4454 0.0581 1.0000 Uiso R . . . . .
H211 H 0.6551 1.1241 0.3869 0.0567 1.0000 Uiso R . . . . .
H221 H 0.5633 0.8232 0.3232 0.0500 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 0.0541(8) 0.0413(8) 0.0564(8) -0.0120(6) 0.0282(7) 0.0065(6)
C2 0.0449(11) 0.0306(11) 0.0308(10) 0.0005(8) 0.0169(9) 0.0079(9)
N3 0.0389(9) 0.0321(9) 0.0340(8) 0.0011(7) 0.0181(7) 0.0043(7)
C4 0.0359(10) 0.0278(10) 0.0281(9) 0.0009(8) 0.0132(8) 0.0018(8)
N5 0.0321(8) 0.0300(9) 0.0334(8) -0.0005(7) 0.0165(7) 0.0018(7)
N6 0.0325(8) 0.0294(9) 0.0333(8) -0.0006(7) 0.0149(7) 0.0032(7)
C7 0.0308(9) 0.0298(10) 0.0304(9) 0.0038(8) 0.0120(8) 0.0004(8)
C8 0.0285(9) 0.0297(10) 0.0295(9) 0.0024(8) 0.0089(8) 0.0040(8)
C9 0.0387(11) 0.0330(11) 0.0328(10) 0.0046(8) 0.0133(8) 0.0010(9)
C10 0.0410(11) 0.0308(11) 0.0389(11) 0.0013(9) 0.0085(9) -0.0012(9)
C11 0.0380(11) 0.0390(12) 0.0378(11) -0.0053(9) 0.0078(9) 0.0063(9)
C12 0.0368(11) 0.0485(13) 0.0388(11) -0.0048(10) 0.0163(9) 0.0034(10)
C13 0.0334(10) 0.0391(12) 0.0385(11) -0.0014(9) 0.0160(9) -0.0014(9)
C14 0.0374(11) 0.0363(11) 0.0404(11) -0.0012(9) 0.0200(9) -0.0031(9)
N15 0.0343(9) 0.0375(10) 0.0418(9) -0.0006(8) 0.0220(8) -0.0015(7)
C16 0.0350(10) 0.0308(10) 0.0370(10) -0.0015(8) 0.0176(8) 0.0017(8)
C17 0.0366(10) 0.0333(10) 0.0299(9) 0.0026(8) 0.0128(8) -0.0000(9)
C18 0.0402(11) 0.0307(10) 0.0279(9) 0.0042(8) 0.0120(8) 0.0016(9)
C19 0.0530(13) 0.0360(12) 0.0382(11) -0.0032(9) 0.0145(10) -0.0004(10)
C20 0.0527(14) 0.0421(13) 0.0437(12) -0.0056(10) 0.0121(11) -0.0147(11)
C21 0.0433(12) 0.0550(15) 0.0419(12) -0.0049(11) 0.0159(10) -0.0116(11)
C22 0.0393(11) 0.0476(13) 0.0381(11) -0.0039(10) 0.0159(9) -0.0040(10)

_refine_ls_extinction_coef       75(17)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.1976(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 . C2 . 1.347(2) yes
C2 . N3 . 1.289(3) yes
C2 . C18 . 1.409(3) yes
N3 . C4 . 1.360(2) yes
C4 . N5 . 1.412(3) yes
C4 . C16 . 1.364(3) yes
N5 . N6 . 1.342(2) yes
N5 . N15 . 1.344(2) yes
N6 . C7 . 1.335(3) yes
C7 . C8 . 1.464(3) yes
C7 . C14 . 1.412(3) yes
C8 . C9 . 1.390(3) yes
C8 . C13 . 1.400(3) yes
C9 . C10 . 1.382(3) yes
C9 . H91 . 0.949 no
C10 . C11 . 1.386(3) yes
C10 . H101 . 0.944 no
C11 . C12 . 1.381(3) yes
C11 . H111 . 0.943 no
C12 . C13 . 1.383(3) yes
C12 . H121 . 0.964 no
C13 . H131 . 0.952 no
C14 . N15 . 1.325(3) yes
C14 . H141 . 0.951 no
C16 . C17 . 1.412(3) yes
C16 . H161 . 0.947 no
C17 . C18 . 1.418(3) yes
C17 . C22 . 1.413(3) yes
C18 . C19 . 1.412(3) yes
C19 . C20 . 1.367(3) yes
C19 . H191 . 0.936 no
C20 . C21 . 1.401(4) yes
C20 . H201 . 0.942 no
C21 . C22 . 1.364(3) yes
C21 . H211 . 0.939 no
C22 . H221 . 0.958 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 . N3 . 115.32(18) yes
F1 . C2 . C18 . 116.77(18) yes
N3 . C2 . C18 . 127.91(19) yes
C2 . N3 . C4 . 115.29(17) yes
N3 . C4 . N5 . 114.77(17) yes
N3 . C4 . C16 . 124.67(19) yes
N5 . C4 . C16 . 120.57(18) yes
C4 . N5 . N6 . 121.27(15) yes
C4 . N5 . N15 . 123.44(16) yes
N6 . N5 . N15 . 115.24(16) yes
N5 . N6 . C7 . 103.91(15) yes
N6 . C7 . C8 . 122.84(17) yes
N6 . C7 . C14 . 107.95(18) yes
C8 . C7 . C14 . 129.17(18) yes
C7 . C8 . C9 . 120.39(18) yes
C7 . C8 . C13 . 120.52(18) yes
C9 . C8 . C13 . 119.05(19) yes
C8 . C9 . C10 . 120.38(19) yes
C8 . C9 . H91 . 119.7 no
C10 . C9 . H91 . 119.9 no
C9 . C10 . C11 . 120.3(2) yes
C9 . C10 . H101 . 120.4 no
C11 . C10 . H101 . 119.3 no
C10 . C11 . C12 . 119.7(2) yes
C10 . C11 . H111 . 119.2 no
C12 . C11 . H111 . 121.0 no
C11 . C12 . C13 . 120.5(2) yes
C11 . C12 . H121 . 120.3 no
C13 . C12 . H121 . 119.3 no
C8 . C13 . C12 . 120.0(2) yes
C8 . C13 . H131 . 119.8 no
C12 . C13 . H131 . 120.1 no
C7 . C14 . N15 . 109.59(18) yes
C7 . C14 . H141 . 127.2 no
N15 . C14 . H141 . 123.2 no
N5 . N15 . C14 . 103.30(16) yes
C4 . C16 . C17 . 118.62(19) yes
C4 . C16 . H161 . 119.3 no
C17 . C16 . H161 . 122.1 no
C16 . C17 . C18 . 118.27(18) yes
C16 . C17 . C22 . 123.23(19) yes
C18 . C17 . C22 . 118.50(19) yes
C17 . C18 . C2 . 115.20(18) yes
C17 . C18 . C19 . 120.12(19) yes
C2 . C18 . C19 . 124.7(2) yes
C18 . C19 . C20 . 119.5(2) yes
C18 . C19 . H191 . 119.5 no
C20 . C19 . H191 . 121.0 no
C19 . C20 . C21 . 120.6(2) yes
C19 . C20 . H201 . 119.7 no
C21 . C20 . H201 . 119.8 no
C20 . C21 . C22 . 121.1(2) yes
C20 . C21 . H211 . 119.4 no
C22 . C21 . H211 . 119.5 no
C17 . C22 . C21 . 120.2(2) yes
C17 . C22 . H221 . 118.3 no
C21 . C22 . H221 . 121.5 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
C14 . H141 . N15 3_545 156 0.95 2.53 3.417(3) yes


_iucr_refine_instructions_details 
;
#
# Punched on 20/08/24 at 17:07:17
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
CONT EXTPARAM 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
END                                                                             
#
# Punched on 20/08/24 at 17:07:17
#
#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
;

