# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1545042'
_audit_update_record             
;
2017-04-20 deposited with the CCDC.
2017-05-17 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                   7.1098(10)
_cell_length_b                   5.6455(8)
_cell_length_c                   14.581(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.522(7)
_cell_angle_gamma                90
_cell_volume                     585.25(14)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_int_tables_number      4
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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            2
_chemical_name_systematic        
1-(1,1,2,2-tetrafluoroethyl)-4-p-tolyl-1H-1,2,3-triazole
_chemical_formula_moiety         'C11 H9 F4 N3'

# Given Formula = C11 H9 F4 N3 
# Dc =      1.47 Fooo =    264.00 Mu =     11.98 M =    259.20
# Found Formula = C11 H9 F4 N3 
# Dc =      1.47 FOOO =    264.00 Mu =     11.98 M =    259.20

_chemical_formula_sum            'C11 H9 F4 N3'
_chemical_compound_source        ?
_chemical_formula_weight         259.20


_cell_measurement_reflns_used    120
_cell_measurement_theta_min      10.5207
_cell_measurement_theta_max      52.5024
_cell_measurement_temperature    180

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      180
_exptl_crystal_size_min          0.052
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_max          0.811

_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    1.198

# Sheldrick geometric approximatio 0.89 0.94 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.94
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_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       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_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            7865
_reflns_number_total             2147
_diffrn_reflns_av_R_equivalents  0.059
# Number of reflections without Friedels Law is 2147 
# Number of reflections with Friedels Law is 1223 
# Theoretical number of reflections is about 1116 


_diffrn_reflns_theta_min         3.031
_diffrn_reflns_theta_max         70.364
_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        70.364
_diffrn_measured_fraction_theta_full 0.991


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              -6
_reflns_limit_k_max              6
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   4.17
_oxford_diffrn_Wilson_scale      4.27

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

_refine_diff_density_min         -0.46
_refine_diff_density_max         0.56


# 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         1878
_refine_ls_number_restraints     33
_refine_ls_number_parameters     165
_oxford_refine_ls_R_factor_ref   0.0820
_refine_ls_wR_factor_ref         0.0921
_refine_ls_goodness_of_fit_ref   1.0405
_refine_ls_shift/su_max          0.0014035
_refine_ls_shift/su_mean         0.0001456


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2140
_refine_ls_R_factor_all          0.0887
_refine_ls_wR_factor_all         0.1027

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1878
_refine_ls_R_factor_gt           0.0820
_refine_ls_wR_factor_gt          0.0921

_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_abs_structure_details 'Flack (1983), 924 Friedel-pairs'


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.779 0.982 0.460 0.169 0.717E-01 
;

# 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 0.7303(9) 0.4159(6) 0.8909(2) 0.1169 1.0000 Uani D . . . . .
C2 C 0.7139(16) 0.6397(13) 0.8912(5) 0.1154 1.0000 Uani D U . . . .
F3 F 0.5143(11) 0.7059(14) 0.9201(5) 0.1645 1.0000 Uani D . . . . .
N4 N 0.7393(7) 0.7258(8) 0.7962(3) 0.0685 1.0000 Uani . U . . . .
N5 N 0.7562(6) 0.9617(7) 0.7826(3) 0.0679 1.0000 Uani . . . . . .
N6 N 0.7624(5) 0.9909(7) 0.6956(2) 0.0575 1.0000 Uani . . . . . .
C7 C 0.7485(5) 0.7786(7) 0.6515(3) 0.0500 1.0000 Uani . . . . . .
C8 C 0.7362(7) 0.6044(8) 0.7159(3) 0.0609 1.0000 Uani . . . . . .
C9 C 0.7505(5) 0.7609(7) 0.5515(3) 0.0436 1.0000 Uani . . . . . .
C10 C 0.6803(5) 0.5596(7) 0.5066(3) 0.0475 1.0000 Uani . . . . . .
C11 C 0.6803(5) 0.5480(8) 0.4133(3) 0.0530 1.0000 Uani . . . . . .
C12 C 0.7525(5) 0.7309(9) 0.3589(3) 0.0583 1.0000 Uani . . . . . .
C13 C 0.8247(5) 0.9297(8) 0.4040(3) 0.0573 1.0000 Uani . . . . . .
C14 C 0.8232(5) 0.9434(7) 0.4979(3) 0.0520 1.0000 Uani . . . . . .
C15 C 0.7525(8) 0.7147(12) 0.2561(4) 0.0782 1.0000 Uani . . . . . .
F16 F 0.9869(15) 0.6954(16) 0.9267(4) 0.1868 1.0000 Uani D U . . . .
F17 F 0.7521(17) 0.6916(12) 1.0404(3) 0.1763 1.0000 Uani D U . . . .
C5 C 0.815(2) 0.7808(18) 0.9580(5) 0.1546 1.0000 Uani D U . . . .
H81 H 0.7264 0.4398 0.7074 0.0726 1.0000 Uiso R . . . . .
H101 H 0.6326 0.4353 0.5410 0.0564 1.0000 Uiso R . . . . .
H111 H 0.6297 0.4165 0.3853 0.0631 1.0000 Uiso R . . . . .
H131 H 0.8759 1.0526 0.3699 0.0693 1.0000 Uiso R . . . . .
H141 H 0.8744 1.0739 0.5263 0.0623 1.0000 Uiso R . . . . .
H153 H 0.8783 0.6849 0.2349 0.1170 1.0000 Uiso R . . . . .
H152 H 0.6720 0.5876 0.2373 0.1167 1.0000 Uiso R . . . . .
H151 H 0.7036 0.8597 0.2301 0.1170 1.0000 Uiso R . . . . .
H51 H 0.7953 0.9521 0.9493 0.1848 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.649(4)

loop_
_oxford_twin_element_scale_factors
0.937(3)
0.063(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
F1 . C2 . 1.269(8) yes
C2 . F3 . 1.530(12) yes
C2 . N4 . 1.482(8) yes
C2 . C5 . 1.444(14) yes
N4 . N5 . 1.352(6) yes
N4 . C8 . 1.356(6) yes
N5 . N6 . 1.281(5) yes
N6 . C7 . 1.363(5) yes
C7 . C8 . 1.363(6) yes
C7 . C9 . 1.462(5) yes
C8 . H81 . 0.940 no
C9 . C10 . 1.401(5) yes
C9 . C14 . 1.395(5) yes
C10 . C11 . 1.362(6) yes
C10 . H101 . 0.929 no
C11 . C12 . 1.402(7) yes
C11 . H111 . 0.919 no
C12 . C13 . 1.397(7) yes
C12 . C15 . 1.502(7) yes
C13 . C14 . 1.371(6) yes
C13 . H131 . 0.930 no
C14 . H141 . 0.919 no
C15 . H153 . 0.964 no
C15 . H152 . 0.956 no
C15 . H151 . 0.965 no
F16 . C5 . 1.395(14) yes
F17 . C5 . 1.381(11) yes
C5 . H51 . 0.985 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 . 109.3(9) yes
F1 . C2 . N4 . 108.2(5) yes
F3 . C2 . N4 . 107.4(7) yes
F1 . C2 . C5 . 120.4(9) yes
F3 . C2 . C5 . 97.8(8) yes
N4 . C2 . C5 . 112.7(7) yes
C2 . N4 . N5 . 118.1(4) yes
C2 . N4 . C8 . 129.8(5) yes
N5 . N4 . C8 . 111.9(4) yes
N4 . N5 . N6 . 106.0(3) yes
N5 . N6 . C7 . 110.5(3) yes
N6 . C7 . C8 . 108.3(4) yes
N6 . C7 . C9 . 121.9(3) yes
C8 . C7 . C9 . 129.7(4) yes
C7 . C8 . N4 . 103.3(4) yes
C7 . C8 . H81 . 128.9 no
N4 . C8 . H81 . 127.9 no
C7 . C9 . C10 . 121.0(3) yes
C7 . C9 . C14 . 121.0(3) yes
C10 . C9 . C14 . 118.0(3) yes
C9 . C10 . C11 . 120.2(3) yes
C9 . C10 . H101 . 119.3 no
C11 . C10 . H101 . 120.5 no
C10 . C11 . C12 . 122.2(3) yes
C10 . C11 . H111 . 118.6 no
C12 . C11 . H111 . 119.2 no
C11 . C12 . C13 . 117.4(4) yes
C11 . C12 . C15 . 121.6(4) yes
C13 . C12 . C15 . 121.1(4) yes
C12 . C13 . C14 . 120.7(4) yes
C12 . C13 . H131 . 119.4 no
C14 . C13 . H131 . 119.9 no
C9 . C14 . C13 . 121.6(3) yes
C9 . C14 . H141 . 119.2 no
C13 . C14 . H141 . 119.2 no
C12 . C15 . H153 . 109.8 no
C12 . C15 . H152 . 109.0 no
H153 . C15 . H152 . 109.4 no
C12 . C15 . H151 . 109.7 no
H153 . C15 . H151 . 110.8 no
H152 . C15 . H151 . 108.2 no
C2 . C5 . F16 . 91.2(8) yes
C2 . C5 . F17 . 102.9(9) yes
F16 . C5 . F17 . 116.7(10) yes
C2 . C5 . H51 . 112.7 no
F16 . C5 . H51 . 114.8 no
F17 . C5 . H51 . 115.1 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
C8 . H81 . N6 1_545 169.42(15) 0.940 2.553 3.481(7) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 20/04/17 at 12:40:45
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
SUMFIX ELEMENT SCALES 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 153,X'S) H   ( 152,X'S) H   ( 151,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 20/04/17 at 12:40:45
#
#LIST     16                                                                    
DISTANCE 1.345000 , 0.020000 = F(1) TO C(2) 
DISTANCE 1.345000 , 0.020000 = C(2) TO F(3) 
DISTANCE 1.345000 , 0.020000 = F(16) TO C(5) 
DISTANCE 1.345000 , 0.020000 = F(17) TO C(5) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
VIBRATION 0.0, 0.020000 = C(2) TO C(5) 
U(IJ)'S  0.0, 0.010000 = C(2) TO C(5) 
VIBRATION 0.0, 0.020000 = C(2) TO N(4) 
U(IJ)'S  0.0, 0.010000 = C(2) TO N(4) 
VIBRATION 0.0, 0.020000 = F(17) TO C(5) 
U(IJ)'S  0.0, 0.010000 = F(17) TO C(5) 
VIBRATION 0.0, 0.020000 = F(16) TO F(17) 
U(IJ)'S  0.0, 0.010000 = F(16) TO F(17) 
END                                                                             
;

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1545040'
_audit_update_record             
;
2017-04-20 deposited with the CCDC.
2017-05-17 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                   18.6519(9)
_cell_length_b                   5.6223(3)
_cell_length_c                   27.0706(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2838.8(2)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_int_tables_number      33
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,y+1/2,z+1/2
x+1/2,-y+1/2,z
-x,-y,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 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            8
_chemical_name_systematic        
1-(2-(4-bromo-1H-pyrazol-1-yl)-1,1,2,2-tetrafluoroethyl)-4-phenyl-1H-1,2,3-triazole
_chemical_formula_moiety         'C13 H8 Br1 F4 N5'

# Given Formula = C11 H9 Br1 F4 N3 
# Dc =      1.59 Fooo =   1536.00 Mu =     43.13 M =    678.22
# Found Formula = C13 H8 Br1 F4 N5 
# Dc =      1.83 FOOO =   1536.00 Mu =     44.61 M =    780.27

_chemical_formula_sum            'C13 H8 Br1 F4 N5'
_chemical_compound_source        ?
_chemical_formula_weight         390.14


_cell_measurement_reflns_used    110
_cell_measurement_theta_min      12.5524
_cell_measurement_theta_max      57.5264
_cell_measurement_temperature    180

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      180
_exptl_crystal_size_min          0.070
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_max          0.307

_exptl_crystal_density_diffrn    1.826
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    4.461

# Sheldrick geometric approximatio 0.69 0.73 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_T_max  0.73
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_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       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_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            21410
_reflns_number_total             5246
_diffrn_reflns_av_R_equivalents  0.049
# Number of reflections without Friedels Law is 5246 
# Number of reflections with Friedels Law is 2746 
# Theoretical number of reflections is about 2695 


_diffrn_reflns_theta_min         3.265
_diffrn_reflns_theta_max         70.046
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        70.046
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       31
_reflns_limit_h_min              0
_reflns_limit_h_max              22
_reflns_limit_k_min              0
_reflns_limit_k_max              6
_reflns_limit_l_min              -32
_reflns_limit_l_max              31

_oxford_diffrn_Wilson_B_factor   2.90
_oxford_diffrn_Wilson_scale      186.29

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

_refine_diff_density_min         -0.38
_refine_diff_density_max         0.38


# 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         4437
_refine_ls_number_restraints     1
_refine_ls_number_parameters     416
_oxford_refine_ls_R_factor_ref   0.0305
_refine_ls_wR_factor_ref         0.0303
_refine_ls_goodness_of_fit_ref   1.0981
_refine_ls_shift/su_max          0.0021416
_refine_ls_shift/su_mean         0.0000639


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5246
_refine_ls_R_factor_all          0.0400
_refine_ls_wR_factor_all         0.0434

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4437
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_gt          0.0303

_refine_ls_abs_structure_Flack   0.054(14)
_refine_ls_abs_structure_details 'Flack (1983), 2500 Friedel-pairs'


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.156 0.122 0.757E-01 0.252E-01 0.120E-01 
;

# 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 1.01121(2) 0.75666(7) 0.75777(3) 0.0377 1.0000 Uani . . . . . .
C2 C 0.9576(2) 0.9294(7) 0.71130(13) 0.0307 1.0000 Uani . . . . . .
C3 C 0.9111(2) 0.8472(7) 0.67713(14) 0.0306 1.0000 Uani . . . . . .
N4 N 0.88615(18) 1.0425(5) 0.65329(12) 0.0322 1.0000 Uani . . . . . .
N5 N 0.9164(2) 1.2471(7) 0.67030(14) 0.0523 1.0000 Uani . . . . . .
C6 C 0.9598(3) 1.1743(8) 0.70526(15) 0.0468 1.0000 Uani . . . . . .
C7 C 0.8401(2) 1.0560(7) 0.61146(16) 0.0353 1.0000 Uani . . . . . .
F8 F 0.80011(12) 0.8584(4) 0.60994(9) 0.0439 1.0000 Uani . . . . . .
F9 F 0.79706(14) 1.2440(5) 0.61580(10) 0.0470 1.0000 Uani . . . . . .
C10 C 0.8808(2) 1.0717(7) 0.56203(14) 0.0330 1.0000 Uani . . . . . .
F11 F 0.91561(12) 0.8665(4) 0.55517(9) 0.0397 1.0000 Uani . . . . . .
F12 F 0.92793(13) 1.2488(4) 0.56383(9) 0.0453 1.0000 Uani . . . . . .
N13 N 0.83392(18) 1.1083(5) 0.52052(11) 0.0312 1.0000 Uani . . . . . .
N14 N 0.8087(2) 1.3317(6) 0.51134(13) 0.0401 1.0000 Uani . . . . . .
N15 N 0.76390(19) 1.3109(6) 0.47488(12) 0.0350 1.0000 Uani . . . . . .
C16 C 0.7591(2) 1.0779(7) 0.46033(13) 0.0288 1.0000 Uani . . . . . .
C17 C 0.8039(2) 0.9490(7) 0.48970(14) 0.0299 1.0000 Uani . . . . . .
C18 C 0.7128(2) 1.0067(7) 0.41905(14) 0.0309 1.0000 Uani . . . . . .
C19 C 0.6585(2) 1.1581(8) 0.40323(15) 0.0386 1.0000 Uani . . . . . .
C20 C 0.6150(2) 1.0957(9) 0.36397(16) 0.0458 1.0000 Uani . . . . . .
Br21 Br 0.76090(2) 0.57582(7) 0.75575(4) 0.0391 1.0000 Uani . . . . . .
C22 C 0.7032(2) 0.7191(7) 0.70729(13) 0.0296 1.0000 Uani . . . . . .
C23 C 0.6920(2) 0.9637(7) 0.70178(14) 0.0333 1.0000 Uani . . . . . .
N24 N 0.6468(2) 1.0071(6) 0.66560(12) 0.0325 1.0000 Uani . . . . . .
N25 N 0.62924(18) 0.7896(5) 0.64800(12) 0.0258 1.0000 Uani . . . . . .
C26 C 0.6628(2) 0.6091(6) 0.67238(13) 0.0269 1.0000 Uani . . . . . .
C27 C 0.58428(19) 0.7680(7) 0.60541(14) 0.0269 1.0000 Uani . . . . . .
F28 F 0.53062(12) 0.9255(4) 0.60778(9) 0.0376 1.0000 Uani . . . . . .
F29 F 0.55654(12) 0.5476(4) 0.60535(8) 0.0353 1.0000 Uani . . . . . .
C30 C 0.6240(2) 0.8038(6) 0.55592(14) 0.0291 1.0000 Uani . . . . . .
F31 F 0.67912(12) 0.6550(4) 0.55453(8) 0.0407 1.0000 Uani . . . . . .
F32 F 0.64849(13) 1.0280(4) 0.55446(9) 0.0392 1.0000 Uani . . . . . .
N33 N 0.57913(17) 0.7672(5) 0.51395(11) 0.0287 1.0000 Uani . . . . . .
N34 N 0.56745(18) 0.5427(6) 0.49720(12) 0.0347 1.0000 Uani . . . . . .
N35 N 0.52332(19) 0.5595(6) 0.45993(12) 0.0348 1.0000 Uani . . . . . .
C36 C 0.5063(2) 0.7949(6) 0.45218(13) 0.0279 1.0000 Uani . . . . . .
C37 C 0.5417(2) 0.9268(7) 0.48695(13) 0.0277 1.0000 Uani . . . . . .
C38 C 0.4583(2) 0.8637(7) 0.41190(14) 0.0292 1.0000 Uani . . . . . .
C39 C 0.4487(2) 0.7147(7) 0.37141(14) 0.0341 1.0000 Uani . . . . . .
C40 C 0.4035(2) 0.7783(8) 0.33299(15) 0.0385 1.0000 Uani . . . . . .
C41 C 0.3684(2) 0.9926(9) 0.33403(16) 0.0384 1.0000 Uani . . . . . .
C42 C 0.3783(2) 1.1434(8) 0.37350(17) 0.0377 1.0000 Uani . . . . . .
C43 C 0.4227(2) 1.0805(7) 0.41260(14) 0.0331 1.0000 Uani . . . . . .
C44 C 0.6791(3) 0.7295(9) 0.35558(15) 0.0461 1.0000 Uani . . . . . .
C1 C 0.6249(2) 0.8818(9) 0.34028(16) 0.0466 1.0000 Uani . . . . . .
C4 C 0.7230(2) 0.7934(8) 0.39466(17) 0.0398 1.0000 Uani . . . . . .
H31 H 0.8977 0.6911 0.6707 0.0374 1.0000 Uiso R . . . . .
H61 H 0.9875 1.2744 0.7237 0.0571 1.0000 Uiso R . . . . .
H171 H 0.8128 0.7869 0.4893 0.0364 1.0000 Uiso R . . . . .
H191 H 0.6515 1.2981 0.4198 0.0458 1.0000 Uiso R . . . . .
H201 H 0.5781 1.1968 0.3538 0.0549 1.0000 Uiso R . . . . .
H231 H 0.7130 1.0814 0.7210 0.0398 1.0000 Uiso R . . . . .
H261 H 0.6584 0.4487 0.6658 0.0315 1.0000 Uiso R . . . . .
H371 H 0.5412 1.0886 0.4918 0.0336 1.0000 Uiso R . . . . .
H391 H 0.4731 0.5708 0.3701 0.0407 1.0000 Uiso R . . . . .
H401 H 0.3979 0.6732 0.3061 0.0459 1.0000 Uiso R . . . . .
H411 H 0.3386 1.0320 0.3077 0.0462 1.0000 Uiso R . . . . .
H421 H 0.3544 1.2890 0.3740 0.0447 1.0000 Uiso R . . . . .
H431 H 0.4277 1.1824 0.4394 0.0407 1.0000 Uiso R . . . . .
H441 H 0.6867 0.5861 0.3400 0.0548 1.0000 Uiso R . . . . .
H11 H 0.5958 0.8410 0.3143 0.0562 1.0000 Uiso R . . . . .
H41 H 0.7596 0.6905 0.4048 0.0478 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       0.000
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.07422(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
Br1 . C2 . 1.877(4) yes
C2 . C3 . 1.350(5) yes
C2 . C6 . 1.387(6) yes
C3 . N4 . 1.355(5) yes
C3 . H31 . 0.929 no
N4 . N5 . 1.362(5) yes
N4 . C7 . 1.423(5) yes
N5 . C6 . 1.311(6) yes
C6 . H61 . 0.912 no
C7 . F8 . 1.339(4) yes
C7 . F9 . 1.333(4) yes
C7 . C10 . 1.540(5) yes
C10 . F11 . 1.337(4) yes
C10 . F12 . 1.330(4) yes
C10 . N13 . 1.438(5) yes
N13 . N14 . 1.364(4) yes
N13 . C17 . 1.346(5) yes
N14 . N15 . 1.299(5) yes
N15 . C16 . 1.371(5) yes
C16 . C17 . 1.362(5) yes
C16 . C18 . 1.468(5) yes
C17 . H171 . 0.927 no
C18 . C19 . 1.390(5) yes
C18 . C4 . 1.382(6) yes
C19 . C20 . 1.383(6) yes
C19 . H191 . 0.915 no
C20 . C1 . 1.376(7) yes
C20 . H201 . 0.934 no
Br21 . C22 . 1.879(4) yes
C22 . C23 . 1.399(5) yes
C22 . C26 . 1.357(5) yes
C23 . N24 . 1.315(5) yes
C23 . H231 . 0.929 no
N24 . N25 . 1.353(5) yes
N25 . C26 . 1.363(5) yes
N25 . C27 . 1.431(5) yes
C26 . H261 . 0.923 no
C27 . F28 . 1.338(4) yes
C27 . F29 . 1.342(4) yes
C27 . C30 . 1.544(5) yes
C30 . F31 . 1.326(4) yes
C30 . F32 . 1.341(4) yes
C30 . N33 . 1.426(5) yes
N33 . N34 . 1.359(4) yes
N33 . C37 . 1.352(5) yes
N34 . N35 . 1.305(4) yes
N35 . C36 . 1.377(5) yes
C36 . C37 . 1.368(5) yes
C36 . C38 . 1.464(5) yes
C37 . H371 . 0.919 no
C38 . C39 . 1.391(5) yes
C38 . C43 . 1.388(6) yes
C39 . C40 . 1.385(5) yes
C39 . H391 . 0.929 no
C40 . C41 . 1.372(6) yes
C40 . H401 . 0.944 no
C41 . C42 . 1.377(6) yes
C41 . H411 . 0.931 no
C42 . C43 . 1.389(6) yes
C42 . H421 . 0.932 no
C43 . H431 . 0.930 no
C44 . C1 . 1.388(7) yes
C44 . C4 . 1.386(6) yes
C44 . H441 . 0.921 no
C1 . H11 . 0.917 no
C4 . H41 . 0.936 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 . 128.6(3) yes
Br1 . C2 . C6 . 125.2(3) yes
C3 . C2 . C6 . 106.1(4) yes
C2 . C3 . N4 . 105.6(3) yes
C2 . C3 . H31 . 128.6 no
N4 . C3 . H31 . 125.8 no
C3 . N4 . N5 . 112.4(3) yes
C3 . N4 . C7 . 129.0(3) yes
N5 . N4 . C7 . 118.3(3) yes
N4 . N5 . C6 . 103.7(3) yes
C2 . C6 . N5 . 112.1(4) yes
C2 . C6 . H61 . 124.4 no
N5 . C6 . H61 . 123.5 no
N4 . C7 . F8 . 108.4(3) yes
N4 . C7 . F9 . 109.6(3) yes
F8 . C7 . F9 . 108.9(3) yes
N4 . C7 . C10 . 113.4(3) yes
F8 . C7 . C10 . 107.2(3) yes
F9 . C7 . C10 . 109.1(3) yes
C7 . C10 . F11 . 108.1(3) yes
C7 . C10 . F12 . 109.7(3) yes
F11 . C10 . F12 . 109.2(3) yes
C7 . C10 . N13 . 112.8(3) yes
F11 . C10 . N13 . 108.1(3) yes
F12 . C10 . N13 . 108.8(3) yes
C10 . N13 . N14 . 118.9(3) yes
C10 . N13 . C17 . 129.9(3) yes
N14 . N13 . C17 . 110.9(3) yes
N13 . N14 . N15 . 106.1(3) yes
N14 . N15 . C16 . 110.3(3) yes
N15 . C16 . C17 . 107.5(3) yes
N15 . C16 . C18 . 121.2(3) yes
C17 . C16 . C18 . 131.3(4) yes
C16 . C17 . N13 . 105.3(3) yes
C16 . C17 . H171 . 128.8 no
N13 . C17 . H171 . 126.0 no
C16 . C18 . C19 . 119.7(4) yes
C16 . C18 . C4 . 121.3(4) yes
C19 . C18 . C4 . 119.0(4) yes
C18 . C19 . C20 . 120.6(4) yes
C18 . C19 . H191 . 118.8 no
C20 . C19 . H191 . 120.6 no
C19 . C20 . C1 . 120.1(4) yes
C19 . C20 . H201 . 120.3 no
C1 . C20 . H201 . 119.6 no
Br21 . C22 . C23 . 125.5(3) yes
Br21 . C22 . C26 . 127.5(3) yes
C23 . C22 . C26 . 106.9(3) yes
C22 . C23 . N24 . 110.9(4) yes
C22 . C23 . H231 . 125.3 no
N24 . C23 . H231 . 123.8 no
C23 . N24 . N25 . 104.5(3) yes
N24 . N25 . C26 . 113.0(3) yes
N24 . N25 . C27 . 120.2(3) yes
C26 . N25 . C27 . 126.6(3) yes
N25 . C26 . C22 . 104.6(3) yes
N25 . C26 . H261 . 126.3 no
C22 . C26 . H261 . 129.0 no
N25 . C27 . F28 . 110.1(3) yes
N25 . C27 . F29 . 107.8(3) yes
F28 . C27 . F29 . 108.8(3) yes
N25 . C27 . C30 . 114.0(3) yes
F28 . C27 . C30 . 108.3(3) yes
F29 . C27 . C30 . 107.7(3) yes
C27 . C30 . F31 . 108.3(3) yes
C27 . C30 . F32 . 108.2(3) yes
F31 . C30 . F32 . 109.1(3) yes
C27 . C30 . N33 . 113.0(3) yes
F31 . C30 . N33 . 110.0(3) yes
F32 . C30 . N33 . 108.2(3) yes
C30 . N33 . N34 . 119.6(3) yes
C30 . N33 . C37 . 129.6(3) yes
N34 . N33 . C37 . 110.7(3) yes
N33 . N34 . N35 . 107.0(3) yes
N34 . N35 . C36 . 109.4(3) yes
N35 . C36 . C37 . 107.8(3) yes
N35 . C36 . C38 . 120.6(3) yes
C37 . C36 . C38 . 131.7(3) yes
C36 . C37 . N33 . 105.1(3) yes
C36 . C37 . H371 . 128.9 no
N33 . C37 . H371 . 125.9 no
C36 . C38 . C39 . 120.4(3) yes
C36 . C38 . C43 . 121.0(3) yes
C39 . C38 . C43 . 118.6(4) yes
C38 . C39 . C40 . 121.0(4) yes
C38 . C39 . H391 . 119.4 no
C40 . C39 . H391 . 119.6 no
C39 . C40 . C41 . 120.1(4) yes
C39 . C40 . H401 . 119.1 no
C41 . C40 . H401 . 120.8 no
C40 . C41 . C42 . 119.5(4) yes
C40 . C41 . H411 . 118.6 no
C42 . C41 . H411 . 121.9 no
C41 . C42 . C43 . 121.0(4) yes
C41 . C42 . H421 . 119.2 no
C43 . C42 . H421 . 119.8 no
C42 . C43 . C38 . 119.9(4) yes
C42 . C43 . H431 . 119.9 no
C38 . C43 . H431 . 120.2 no
C1 . C44 . C4 . 119.9(5) yes
C1 . C44 . H441 . 121.0 no
C4 . C44 . H441 . 119.1 no
C44 . C1 . C20 . 119.8(4) yes
C44 . C1 . H11 . 120.4 no
C20 . C1 . H11 . 119.8 no
C44 . C4 . C18 . 120.5(4) yes
C44 . C4 . H41 . 119.6 no
C18 . C4 . H41 . 119.9 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C3 . H31 . N5 1_545 154.11(13) 0.929 2.521 3.381(6) yes
C26 . H261 . N24 1_545 168.87(11) 0.923 2.492 3.402(6) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 04/04/17 at 14:21:37
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE C   (  42,X'S) H   ( 421,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (   1,X'S) H   (  11,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 04/04/17 at 14:21:37
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1545039'
_audit_update_record             
;
2017-04-20 deposited with the CCDC.
2017-05-17 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                   16.0915(14)
_cell_length_b                   7.1728(6)
_cell_length_c                   31.911(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.303(3)
_cell_angle_gamma                90
_cell_volume                     3569.0(5)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_int_tables_number      15

# 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 .
_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 0.0181 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'
I -0.3257 6.8362 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8
_chemical_name_systematic        
5-iodo-4-phenyl-1-(1,1,2,2-tetrafluoro-2-(4-methoxyphenoxy)ethyl)-1H-1,2,3-triazole
_chemical_formula_moiety         'C17 H12 F4 I1 N3 O2'

# Given Formula = C17 H12 F4 I1 N3 O2 
# Dc =      1.84 Fooo =   1920.00 Mu =    146.49 M =    493.20
# Found Formula = C17 H12 F4 I1 N3 O2 
# Dc =      1.84 FOOO =   1920.00 Mu =    146.49 M =    493.20

_chemical_formula_sum            'C17 H12 F4 I1 N3 O2'
_chemical_compound_source        ?
_chemical_formula_weight         493.20


_cell_measurement_reflns_used    214
_cell_measurement_theta_min      10.3841
_cell_measurement_theta_max      59.2898
_cell_measurement_temperature    180

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      180
_exptl_crystal_size_min          0.135
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_max          0.369

_exptl_crystal_density_diffrn    1.836
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1920
_exptl_absorpt_coefficient_mu    14.649

# Sheldrick geometric approximatio 0.10 0.14 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.07
_exptl_absorpt_correction_T_max  0.14
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_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       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_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            27846
_reflns_number_total             3282
_diffrn_reflns_av_R_equivalents  0.077
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3282 
# Theoretical number of reflections is about 6534 


_diffrn_reflns_theta_min         2.858
_diffrn_reflns_theta_max         68.238
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        68.238
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_reflns_limit_h_min              -19
_reflns_limit_h_max              18
_reflns_limit_k_min              0
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              38

_oxford_diffrn_Wilson_B_factor   2.77
_oxford_diffrn_Wilson_scale      972.94

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

_refine_diff_density_min         -1.02
_refine_diff_density_max         2.80


# 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         2180
_refine_ls_number_restraints     0
_refine_ls_number_parameters     244
_oxford_refine_ls_R_factor_ref   0.0879
_refine_ls_wR_factor_ref         0.0831
_refine_ls_goodness_of_fit_ref   1.1113
_refine_ls_shift/su_max          0.0007961
_refine_ls_shift/su_mean         0.0001546


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3278
_refine_ls_R_factor_all          0.1225
_refine_ls_wR_factor_all         0.1026

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2180
_refine_ls_R_factor_gt           0.0879
_refine_ls_wR_factor_gt          0.0831


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 1.39 2.06 1.35 0.580 0.223 
;

# 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
I1 I 0.47687(5) 1.24644(12) 0.324130(19) 0.0415 1.0000 Uani . . . . . .
C2 C 0.4830(7) 0.9584(14) 0.3317(3) 0.0309 1.0000 Uani . . . . . .
N3 N 0.5308(6) 0.8687(12) 0.3679(2) 0.0314 1.0000 Uani . . . . . .
N4 N 0.5235(7) 0.6848(13) 0.3628(3) 0.0346 1.0000 Uani . . . . . .
N5 N 0.4717(6) 0.6495(13) 0.3248(3) 0.0345 1.0000 Uani . . . . . .
C6 C 0.4427(7) 0.8174(16) 0.3055(3) 0.0313 1.0000 Uani . . . . . .
C7 C 0.3850(8) 0.8191(17) 0.2624(3) 0.0373 1.0000 Uani . . . . . .
C8 C 0.3825(8) 0.668(2) 0.2347(4) 0.0490 1.0000 Uani . . . . . .
C9 C 0.3295(8) 0.673(2) 0.1923(4) 0.0550 1.0000 Uani . . . . . .
C10 C 0.2768(9) 0.818(2) 0.1787(4) 0.0558 1.0000 Uani . . . . . .
C11 C 0.2749(10) 0.963(2) 0.2050(4) 0.0636 1.0000 Uani . . . . . .
C12 C 0.3276(8) 0.9679(18) 0.2472(4) 0.0487 1.0000 Uani . . . . . .
C13 C 0.5870(8) 0.9468(15) 0.4058(3) 0.0361 1.0000 Uani . . . . . .
F14 F 0.6464(5) 1.0502(10) 0.3949(2) 0.0512 1.0000 Uani . . . . . .
F15 F 0.5394(5) 1.0629(10) 0.42381(18) 0.0507 1.0000 Uani . . . . . .
C16 C 0.6293(7) 0.8029(16) 0.4407(3) 0.0348 1.0000 Uani . . . . . .
F17 F 0.6839(4) 0.6992(10) 0.4249(2) 0.0488 1.0000 Uani . . . . . .
F18 F 0.6795(4) 0.9072(11) 0.47240(19) 0.0492 1.0000 Uani . . . . . .
O19 O 0.5706(5) 0.7076(12) 0.45353(19) 0.0396 1.0000 Uani . . . . . .
C20 C 0.5985(7) 0.5959(16) 0.4927(3) 0.0343 1.0000 Uani . . . . . .
C21 C 0.5860(6) 0.6739(17) 0.5305(3) 0.0311 1.0000 Uani . . . . . .
C22 C 0.6065(7) 0.5651(17) 0.5670(3) 0.0373 1.0000 Uani . . . . . .
C23 C 0.6394(7) 0.3894(19) 0.5665(3) 0.0405 1.0000 Uani . . . . . .
O24 O 0.6576(6) 0.2971(14) 0.6058(3) 0.0608 1.0000 Uani . . . . . .
C25 C 0.6925(11) 0.115(2) 0.6071(5) 0.0706 1.0000 Uani . . . . . .
C26 C 0.6532(7) 0.3192(18) 0.5288(3) 0.0403 1.0000 Uani . . . . . .
C27 C 0.6312(7) 0.4263(18) 0.4911(3) 0.0376 1.0000 Uani . . . . . .
H81 H 0.4153 0.5632 0.2443 0.0711 1.0000 Uiso R . . . . .
H91 H 0.3300 0.5758 0.1733 0.0691 1.0000 Uiso R . . . . .
H101 H 0.2384 0.8149 0.1514 0.0760 1.0000 Uiso R . . . . .
H111 H 0.2428 1.0668 0.1938 0.0860 1.0000 Uiso R . . . . .
H121 H 0.3234 1.0667 0.2653 0.0690 1.0000 Uiso R . . . . .
H211 H 0.5633 0.7925 0.5316 0.0461 1.0000 Uiso R . . . . .
H221 H 0.6032 0.6164 0.5932 0.0511 1.0000 Uiso R . . . . .
H252 H 0.6948 0.0619 0.6349 0.1129 1.0000 Uiso R . . . . .
H251 H 0.7494 0.1205 0.6028 0.1130 1.0000 Uiso R . . . . .
H253 H 0.6571 0.0384 0.5849 0.1130 1.0000 Uiso R . . . . .
H261 H 0.6768 0.2009 0.5293 0.0571 1.0000 Uiso R . . . . .
H271 H 0.6374 0.3777 0.4649 0.0510 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.03363(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
I1 . C2 . 2.079(10) yes
C2 . N3 . 1.379(13) yes
C2 . C6 . 1.369(15) yes
N3 . N4 . 1.331(13) yes
N3 . C13 . 1.434(13) yes
N4 . N5 . 1.315(12) yes
N5 . C6 . 1.381(14) yes
C6 . C7 . 1.456(15) yes
C7 . C8 . 1.392(18) yes
C7 . C12 . 1.416(17) yes
C8 . C9 . 1.411(17) yes
C8 . H81 . 0.926 no
C9 . C10 . 1.35(2) yes
C9 . H91 . 0.925 no
C10 . C11 . 1.34(2) yes
C10 . H101 . 0.936 no
C11 . C12 . 1.401(16) yes
C11 . H111 . 0.928 no
C12 . H121 . 0.928 no
C13 . F14 . 1.323(14) yes
C13 . F15 . 1.352(13) yes
C13 . C16 . 1.547(14) yes
C16 . F17 . 1.339(14) yes
C16 . F18 . 1.353(12) yes
C16 . O19 . 1.312(14) yes
O19 . C20 . 1.459(12) yes
C20 . C21 . 1.389(15) yes
C20 . C27 . 1.331(17) yes
C21 . C22 . 1.372(15) yes
C21 . H211 . 0.930 no
C22 . C23 . 1.368(18) yes
C22 . H221 . 0.927 no
C23 . O24 . 1.385(13) yes
C23 . C26 . 1.371(16) yes
O24 . C25 . 1.418(19) yes
C25 . H252 . 0.959 no
C25 . H251 . 0.958 no
C25 . H253 . 0.964 no
C26 . C27 . 1.398(16) yes
C26 . H261 . 0.928 no
C27 . H271 . 0.934 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
I1 . C2 . N3 . 124.1(7) yes
I1 . C2 . C6 . 131.5(8) yes
N3 . C2 . C6 . 104.4(9) yes
C2 . N3 . N4 . 110.3(8) yes
C2 . N3 . C13 . 129.1(9) yes
N4 . N3 . C13 . 120.5(9) yes
N3 . N4 . N5 . 108.7(8) yes
N4 . N5 . C6 . 108.1(8) yes
N5 . C6 . C2 . 108.4(8) yes
N5 . C6 . C7 . 119.7(10) yes
C2 . C6 . C7 . 131.7(11) yes
C6 . C7 . C8 . 120.3(11) yes
C6 . C7 . C12 . 122.7(11) yes
C8 . C7 . C12 . 117.1(10) yes
C7 . C8 . C9 . 120.3(13) yes
C7 . C8 . H81 . 119.9 no
C9 . C8 . H81 . 119.8 no
C8 . C9 . C10 . 120.7(13) yes
C8 . C9 . H91 . 120.6 no
C10 . C9 . H91 . 118.7 no
C9 . C10 . C11 . 120.5(11) yes
C9 . C10 . H101 . 119.8 no
C11 . C10 . H101 . 119.6 no
C10 . C11 . C12 . 121.4(13) yes
C10 . C11 . H111 . 118.5 no
C12 . C11 . H111 . 119.7 no
C7 . C12 . C11 . 119.8(12) yes
C7 . C12 . H121 . 120.2 no
C11 . C12 . H121 . 120.0 no
N3 . C13 . F14 . 110.0(8) yes
N3 . C13 . F15 . 107.1(9) yes
F14 . C13 . F15 . 106.8(9) yes
N3 . C13 . C16 . 114.8(9) yes
F14 . C13 . C16 . 110.2(10) yes
F15 . C13 . C16 . 107.5(8) yes
C13 . C16 . F17 . 108.3(8) yes
C13 . C16 . F18 . 104.1(9) yes
F17 . C16 . F18 . 105.3(9) yes
C13 . C16 . O19 . 110.4(9) yes
F17 . C16 . O19 . 114.7(10) yes
F18 . C16 . O19 . 113.3(9) yes
C16 . O19 . C20 . 117.5(8) yes
O19 . C20 . C21 . 116.3(10) yes
O19 . C20 . C27 . 120.6(9) yes
C21 . C20 . C27 . 123.0(10) yes
C20 . C21 . C22 . 116.9(11) yes
C20 . C21 . H211 . 122.8 no
C22 . C21 . H211 . 120.3 no
C21 . C22 . C23 . 121.8(10) yes
C21 . C22 . H221 . 118.9 no
C23 . C22 . H221 . 119.0 no
C22 . C23 . O24 . 115.2(10) yes
C22 . C23 . C26 . 119.7(10) yes
O24 . C23 . C26 . 125.1(12) yes
C23 . O24 . C25 . 117.3(11) yes
O24 . C25 . H252 . 108.5 no
O24 . C25 . H251 . 110.2 no
H252 . C25 . H251 . 109.2 no
O24 . C25 . H253 . 110.3 no
H252 . C25 . H253 . 109.4 no
H251 . C25 . H253 . 109.3 no
C23 . C26 . C27 . 119.5(12) yes
C23 . C26 . H261 . 118.4 no
C27 . C26 . H261 . 122.2 no
C26 . C27 . C20 . 119.2(10) yes
C26 . C27 . H271 . 120.4 no
C20 . C27 . H271 . 120.4 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 04/04/17 at 12:16:51
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  25,X'S) H   ( 252,X'S) H   ( 251,X'S) H   ( 253,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 04/04/17 at 12:16:51
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-4 0 2 x .
2 0 6 x .
2 0 0 x .
2 0 12 x .

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1545038'
_audit_update_record             
;
2017-04-20 deposited with the CCDC.
2017-05-17 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                   18.5871(12)
_cell_length_b                   5.6567(4)
_cell_length_c                   15.3181(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.884(6)
_cell_angle_gamma                90
_cell_volume                     1602.08(19)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14

# 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 .
_symmetry_space_group_name_Hall  ?
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        
4-phenyl-1-(1,1,2,2-tetrafluoro-2-(4-methoxyphenoxy)ethyl)-1H-1,2,3-triazole
_chemical_formula_moiety         'C17 H13 F4 N3 O2'

# Given Formula = C17 H13 F4 N3 O2 
# Dc =      1.52 Fooo =    752.00 Mu =     11.62 M =    367.30
# Found Formula = C17 H13 F4 N3 O2 
# Dc =      1.52 FOOO =    752.00 Mu =     11.62 M =    367.30

_chemical_formula_sum            'C17 H13 F4 N3 O2'
_chemical_compound_source        ?
_chemical_formula_weight         367.30


_cell_measurement_reflns_used    2987
_cell_measurement_theta_min      5.7750
_cell_measurement_theta_max      75.7730
_cell_measurement_temperature    180

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      180
_exptl_crystal_size_min          0.150
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_max          0.620

_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    1.162

# Sheldrick geometric approximatio 0.71 0.84 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.84
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    '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            6578
_reflns_number_total             3165
_diffrn_reflns_av_R_equivalents  0.043
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3165 
# Theoretical number of reflections is about 6683 


_diffrn_reflns_theta_min         4.783
_diffrn_reflns_theta_max         75.910
_diffrn_measured_fraction_theta_max 0.946

_diffrn_reflns_theta_full        68.976
_diffrn_measured_fraction_theta_full 0.987


_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -23
_reflns_limit_h_max              23
_reflns_limit_k_min              0
_reflns_limit_k_max              6
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   3.31
_oxford_diffrn_Wilson_scale      0.08

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

_refine_diff_density_min         -0.31
_refine_diff_density_max         0.31


# 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         2402
_refine_ls_number_restraints     0
_refine_ls_number_parameters     236
_oxford_refine_ls_R_factor_ref   0.0477
_refine_ls_wR_factor_ref         0.0476
_refine_ls_goodness_of_fit_ref   1.1449
_refine_ls_shift/su_max          0.0004556
_refine_ls_shift/su_mean         0.0000539


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3165
_refine_ls_R_factor_all          0.0636
_refine_ls_wR_factor_all         0.0543

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2402
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_gt          0.0476


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 7.51 -2.16 6.14 
;

# 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 0.19845(7) 0.7272(2) 0.56527(9) 0.0618 1.0000 Uani . . . . . .
C2 C 0.20621(10) 0.4919(4) 0.56073(13) 0.0427 1.0000 Uani . . . . . .
F3 F 0.14138(6) 0.4097(3) 0.52604(8) 0.0655 1.0000 Uani . . . . . .
O4 O 0.22750(7) 0.3959(2) 0.63921(8) 0.0424 1.0000 Uani . . . . . .
C5 C 0.17742(9) 0.4035(3) 0.70305(12) 0.0373 1.0000 Uani . . . . . .
C6 C 0.12778(10) 0.2259(3) 0.70558(14) 0.0453 1.0000 Uani . . . . . .
C7 C 0.08064(10) 0.2255(3) 0.77000(14) 0.0438 1.0000 Uani . . . . . .
C8 C 0.08461(9) 0.4042(3) 0.83187(12) 0.0381 1.0000 Uani . . . . . .
O9 O 0.04032(7) 0.4241(3) 0.89727(9) 0.0501 1.0000 Uani . . . . . .
C10 C -0.01015(11) 0.2389(4) 0.90636(15) 0.0543 1.0000 Uani . . . . . .
C11 C 0.13558(10) 0.5817(4) 0.82877(12) 0.0451 1.0000 Uani . . . . . .
C12 C 0.26245(11) 0.4301(4) 0.49692(13) 0.0436 1.0000 Uani . . . . . .
F13 F 0.23845(7) 0.5180(3) 0.41787(7) 0.0610 1.0000 Uani . . . . . .
F14 F 0.26613(6) 0.1964(2) 0.49078(8) 0.0515 1.0000 Uani . . . . . .
N15 N 0.33336(8) 0.5212(3) 0.52290(10) 0.0398 1.0000 Uani . . . . . .
N16 N 0.34810(11) 0.7512(3) 0.50763(13) 0.0567 1.0000 Uani . . . . . .
N17 N 0.41383(10) 0.7888(3) 0.54368(13) 0.0529 1.0000 Uani . . . . . .
C18 C 0.44126(10) 0.5863(3) 0.58252(11) 0.0365 1.0000 Uani . . . . . .
C19 C 0.39007(10) 0.4141(3) 0.56982(11) 0.0355 1.0000 Uani . . . . . .
C20 C 0.51420(10) 0.5805(3) 0.63031(11) 0.0362 1.0000 Uani . . . . . .
C21 C 0.56116(12) 0.7706(3) 0.62497(14) 0.0467 1.0000 Uani . . . . . .
C22 C 0.62853(12) 0.7702(4) 0.67309(16) 0.0550 1.0000 Uani . . . . . .
C23 C 0.64965(11) 0.5798(4) 0.72633(14) 0.0516 1.0000 Uani . . . . . .
C24 C 0.60418(11) 0.3885(4) 0.73083(12) 0.0450 1.0000 Uani . . . . . .
C25 C 0.53619(10) 0.3893(3) 0.68340(12) 0.0386 1.0000 Uani . . . . . .
C1 C 0.18262(10) 0.5816(4) 0.76454(12) 0.0437 1.0000 Uani . . . . . .
H61 H 0.1258 0.1033 0.6645 0.0536 1.0000 Uiso R . . . . .
H71 H 0.0471 0.1055 0.7711 0.0537 1.0000 Uiso R . . . . .
H101 H -0.0358 0.2815 0.9556 0.0803 1.0000 Uiso R . . . . .
H102 H 0.0160 0.0863 0.9181 0.0804 1.0000 Uiso R . . . . .
H103 H -0.0441 0.2263 0.8520 0.0799 1.0000 Uiso R . . . . .
H111 H 0.1384 0.6980 0.8714 0.0538 1.0000 Uiso R . . . . .
H191 H 0.3918 0.2567 0.5882 0.0437 1.0000 Uiso R . . . . .
H211 H 0.5467 0.9003 0.5906 0.0561 1.0000 Uiso R . . . . .
H221 H 0.6596 0.8999 0.6685 0.0656 1.0000 Uiso R . . . . .
H231 H 0.6961 0.5830 0.7603 0.0617 1.0000 Uiso R . . . . .
H241 H 0.6188 0.2528 0.7657 0.0539 1.0000 Uiso R . . . . .
H251 H 0.5048 0.2608 0.6862 0.0465 1.0000 Uiso R . . . . .
H11 H 0.2187 0.7028 0.7631 0.0525 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       39(5)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          3.643(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 . C2 . 1.341(2) yes
C2 . F3 . 1.349(2) yes
C2 . O4 . 1.341(2) yes
C2 . C12 . 1.543(3) yes
O4 . C5 . 1.418(2) yes
C5 . C6 . 1.367(3) yes
C5 . C1 . 1.376(3) yes
C6 . C7 . 1.385(3) yes
C6 . H61 . 0.935 no
C7 . C8 . 1.382(3) yes
C7 . H71 . 0.924 no
C8 . O9 . 1.365(2) yes
C8 . C11 . 1.385(3) yes
O9 . C10 . 1.422(2) yes
C10 . H101 . 0.963 no
C10 . H102 . 0.998 no
C10 . H103 . 0.994 no
C11 . C1 . 1.382(3) yes
C11 . H111 . 0.925 no
C12 . F13 . 1.342(2) yes
C12 . F14 . 1.328(2) yes
C12 . N15 . 1.433(3) yes
N15 . N16 . 1.355(2) yes
N15 . C19 . 1.356(2) yes
N16 . N17 . 1.306(3) yes
N17 . C18 . 1.365(2) yes
C18 . C19 . 1.362(3) yes
C18 . C20 . 1.474(3) yes
C19 . H191 . 0.933 no
C20 . C21 . 1.393(3) yes
C20 . C25 . 1.389(3) yes
C21 . C22 . 1.386(3) yes
C21 . H211 . 0.927 no
C22 . C23 . 1.383(3) yes
C22 . H221 . 0.941 no
C23 . C24 . 1.379(3) yes
C23 . H231 . 0.962 no
C24 . C25 . 1.392(3) yes
C24 . H241 . 0.958 no
C25 . H251 . 0.936 no
C1 . H11 . 0.961 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 . 105.42(15) yes
F1 . C2 . O4 . 112.25(17) yes
F3 . C2 . O4 . 112.52(17) yes
F1 . C2 . C12 . 109.96(16) yes
F3 . C2 . C12 . 107.95(17) yes
O4 . C2 . C12 . 108.62(14) yes
C2 . O4 . C5 . 116.85(13) yes
O4 . C5 . C6 . 119.34(17) yes
O4 . C5 . C1 . 119.27(16) yes
C6 . C5 . C1 . 121.27(17) yes
C5 . C6 . C7 . 119.95(18) yes
C5 . C6 . H61 . 120.4 no
C7 . C6 . H61 . 119.6 no
C6 . C7 . C8 . 119.62(17) yes
C6 . C7 . H71 . 119.5 no
C8 . C7 . H71 . 120.9 no
C7 . C8 . O9 . 124.73(16) yes
C7 . C8 . C11 . 119.68(17) yes
O9 . C8 . C11 . 115.58(17) yes
C8 . O9 . C10 . 117.69(16) yes
O9 . C10 . H101 . 106.0 no
O9 . C10 . H102 . 109.9 no
H101 . C10 . H102 . 110.3 no
O9 . C10 . H103 . 109.8 no
H101 . C10 . H103 . 110.6 no
H102 . C10 . H103 . 110.1 no
C8 . C11 . C1 . 120.64(18) yes
C8 . C11 . H111 . 118.7 no
C1 . C11 . H111 . 120.6 no
C2 . C12 . F13 . 107.67(14) yes
C2 . C12 . F14 . 108.30(17) yes
F13 . C12 . F14 . 108.65(17) yes
C2 . C12 . N15 . 113.96(17) yes
F13 . C12 . N15 . 109.16(17) yes
F14 . C12 . N15 . 108.98(15) yes
C12 . N15 . N16 . 119.61(15) yes
C12 . N15 . C19 . 128.98(16) yes
N16 . N15 . C19 . 111.14(16) yes
N15 . N16 . N17 . 106.29(15) yes
N16 . N17 . C18 . 109.81(17) yes
N17 . C18 . C19 . 108.29(17) yes
N17 . C18 . C20 . 121.24(17) yes
C19 . C18 . C20 . 130.45(16) yes
C18 . C19 . N15 . 104.47(16) yes
C18 . C19 . H191 . 129.5 no
N15 . C19 . H191 . 126.0 no
C18 . C20 . C21 . 120.24(17) yes
C18 . C20 . C25 . 120.59(16) yes
C21 . C20 . C25 . 119.14(19) yes
C20 . C21 . C22 . 120.3(2) yes
C20 . C21 . H211 . 119.8 no
C22 . C21 . H211 . 119.9 no
C21 . C22 . C23 . 120.08(19) yes
C21 . C22 . H221 . 119.1 no
C23 . C22 . H221 . 120.8 no
C22 . C23 . C24 . 120.1(2) yes
C22 . C23 . H231 . 119.3 no
C24 . C23 . H231 . 120.6 no
C23 . C24 . C25 . 120.0(2) yes
C23 . C24 . H241 . 121.1 no
C25 . C24 . H241 . 118.9 no
C24 . C25 . C20 . 120.35(17) yes
C24 . C25 . H251 . 120.7 no
C20 . C25 . H251 . 119.0 no
C11 . C1 . C5 . 118.84(17) yes
C11 . C1 . H11 . 120.7 no
C5 . C1 . H11 . 120.5 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 29/03/17 at 14:36:42
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) H   ( 103,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (   1,X'S) H   (  11,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 29/03/17 at 14:36:42
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1545041'
_audit_update_record             
;
2017-04-20 deposited with the CCDC.
2017-05-17 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                   5.3006(6)
_cell_length_b                   8.6660(10)
_cell_length_c                   35.753(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1642.3(3)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_int_tables_number      19
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 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'
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            4
_chemical_name_systematic        
1-(1,1,2,2-tetrafluoro-2-(phenylthio)ethyl)-4-(p-tolyl)-1H-1,2,3-triazole
_chemical_formula_moiety         'C17 H13 F4 N3 S1'

# Given Formula = C17 H13 F4 N3 S1 
# Dc =      1.49 Fooo =    752.00 Mu =     21.96 M =    367.37
# Found Formula = C17 H13 F4 N3 S1 
# Dc =      1.49 FOOO =    752.00 Mu =     21.96 M =    367.37

_chemical_formula_sum            'C17 H13 F4 N3 S1'
_chemical_compound_source        ?
_chemical_formula_weight         367.37


_cell_measurement_reflns_used    166
_cell_measurement_theta_min      10.4851
_cell_measurement_theta_max      54.9020
_cell_measurement_temperature    180

_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'

_diffrn_ambient_temperature      180
_exptl_crystal_size_min          0.058
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_max          0.626

_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    2.196

# Sheldrick geometric approximatio 0.46 0.88 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.88
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_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       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_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            19043
_reflns_number_total             3016
_diffrn_reflns_av_R_equivalents  0.057
# Number of reflections without Friedels Law is 3016 
# Number of reflections with Friedels Law is 1808 
# Theoretical number of reflections is about 1503 


_diffrn_reflns_theta_min         2.472
_diffrn_reflns_theta_max         68.227
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        68.227
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       42
_reflns_limit_h_min              -6
_reflns_limit_h_max              6
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              42

_oxford_diffrn_Wilson_B_factor   3.42
_oxford_diffrn_Wilson_scale      19.19

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

_refine_diff_density_min         -0.36
_refine_diff_density_max         0.40


# 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         2465
_refine_ls_number_restraints     0
_refine_ls_number_parameters     227
_oxford_refine_ls_R_factor_ref   0.0621
_refine_ls_wR_factor_ref         0.0587
_refine_ls_goodness_of_fit_ref   0.9687
_refine_ls_shift/su_max          0.0010944
_refine_ls_shift/su_mean         0.0000284


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3015
_refine_ls_R_factor_all          0.0773
_refine_ls_wR_factor_all         0.0679

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2465
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_gt          0.0587

_refine_ls_abs_structure_Flack   0.14(3)
_refine_ls_abs_structure_details 'Flack (1983), 1208 Friedel-pairs'


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.533 0.427 0.300 
;

# 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
S1 S 0.8079(2) 0.33487(12) 0.56596(3) 0.0470 1.0000 Uani . . . . . .
C2 C 0.5704(8) 0.4664(5) 0.55107(11) 0.0409 1.0000 Uani . . . . . .
C3 C 0.4267(9) 0.4314(5) 0.51984(11) 0.0480 1.0000 Uani . . . . . .
C4 C 0.2381(10) 0.5312(5) 0.50912(12) 0.0569 1.0000 Uani . . . . . .
C5 C 0.1883(9) 0.6640(6) 0.52929(12) 0.0578 1.0000 Uani . . . . . .
C6 C 0.3342(10) 0.6992(5) 0.56019(12) 0.0547 1.0000 Uani . . . . . .
C7 C 0.5269(9) 0.6008(5) 0.57110(11) 0.0484 1.0000 Uani . . . . . .
C8 C 0.6193(8) 0.2281(5) 0.59859(12) 0.0466 1.0000 Uani . . . . . .
F9 F 0.4249(5) 0.1553(3) 0.58170(7) 0.0640 1.0000 Uani . . . . . .
F10 F 0.5139(5) 0.3222(3) 0.62451(7) 0.0633 1.0000 Uani . . . . . .
C11 C 0.7713(8) 0.1071(5) 0.62050(12) 0.0460 1.0000 Uani . . . . . .
F12 F 0.9738(4) 0.1720(3) 0.63534(7) 0.0556 1.0000 Uani . . . . . .
F13 F 0.8412(6) -0.0065(3) 0.59692(7) 0.0667 1.0000 Uani . . . . . .
N14 N 0.6243(7) 0.0391(4) 0.65053(9) 0.0437 1.0000 Uani . . . . . .
N15 N 0.4461(8) -0.0694(4) 0.64333(10) 0.0526 1.0000 Uani . . . . . .
N16 N 0.3202(8) -0.0877(4) 0.67382(10) 0.0519 1.0000 Uani . . . . . .
C17 C 0.4077(8) 0.0107(4) 0.70106(11) 0.0405 1.0000 Uani . . . . . .
C18 C 0.6041(8) 0.0926(5) 0.68582(11) 0.0450 1.0000 Uani . . . . . .
C19 C 0.2969(8) 0.0144(4) 0.73834(11) 0.0392 1.0000 Uani . . . . . .
C20 C 0.3895(8) 0.1090(5) 0.76618(11) 0.0442 1.0000 Uani . . . . . .
C21 C 0.2712(9) 0.1175(5) 0.80053(11) 0.0481 1.0000 Uani . . . . . .
C22 C 0.0583(8) 0.0327(5) 0.80886(12) 0.0457 1.0000 Uani . . . . . .
C23 C -0.0748(9) 0.0513(6) 0.84586(13) 0.0581 1.0000 Uani . . . . . .
C24 C -0.0315(8) -0.0661(5) 0.78115(13) 0.0494 1.0000 Uani . . . . . .
C25 C 0.0834(8) -0.0757(5) 0.74659(12) 0.0488 1.0000 Uani . . . . . .
H31 H 0.4566 0.3396 0.5065 0.0583 1.0000 Uiso R . . . . .
H41 H 0.1436 0.5088 0.4882 0.0680 1.0000 Uiso R . . . . .
H51 H 0.0602 0.7295 0.5224 0.0688 1.0000 Uiso R . . . . .
H61 H 0.3062 0.7899 0.5737 0.0656 1.0000 Uiso R . . . . .
H71 H 0.6278 0.6227 0.5917 0.0576 1.0000 Uiso R . . . . .
H181 H 0.7070 0.1673 0.6970 0.0543 1.0000 Uiso R . . . . .
H201 H 0.5328 0.1698 0.7616 0.0526 1.0000 Uiso R . . . . .
H211 H 0.3390 0.1835 0.8188 0.0586 1.0000 Uiso R . . . . .
H231 H -0.2525 0.0525 0.8424 0.0874 1.0000 Uiso R . . . . .
H232 H -0.0310 -0.0310 0.8624 0.0867 1.0000 Uiso R . . . . .
H233 H -0.0259 0.1474 0.8568 0.0873 1.0000 Uiso R . . . . .
H241 H -0.1681 -0.1272 0.7860 0.0586 1.0000 Uiso R . . . . .
H251 H 0.0186 -0.1408 0.7286 0.0584 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2382(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
S1 . C2 . 1.779(4) yes
S1 . C8 . 1.794(4) yes
C2 . C3 . 1.385(6) yes
C2 . C7 . 1.387(6) yes
C3 . C4 . 1.376(7) yes
C3 . H31 . 0.941 no
C4 . C5 . 1.384(7) yes
C4 . H41 . 0.921 no
C5 . C6 . 1.383(7) yes
C5 . H51 . 0.919 no
C6 . C7 . 1.387(7) yes
C6 . H61 . 0.934 no
C7 . H71 . 0.929 no
C8 . F9 . 1.351(5) yes
C8 . F10 . 1.355(5) yes
C8 . C11 . 1.537(6) yes
C11 . F12 . 1.323(5) yes
C11 . F13 . 1.348(5) yes
C11 . N14 . 1.452(5) yes
N14 . N15 . 1.357(5) yes
N14 . C18 . 1.349(5) yes
N15 . N16 . 1.288(5) yes
N16 . C17 . 1.375(5) yes
C17 . C18 . 1.373(6) yes
C17 . C19 . 1.457(6) yes
C18 . H181 . 0.936 no
C19 . C20 . 1.380(6) yes
C19 . C25 . 1.406(6) yes
C20 . C21 . 1.381(6) yes
C20 . H201 . 0.939 no
C21 . C22 . 1.379(6) yes
C21 . H211 . 0.939 no
C22 . C23 . 1.508(6) yes
C22 . C24 . 1.393(6) yes
C23 . H231 . 0.950 no
C23 . H232 . 0.955 no
C23 . H233 . 0.957 no
C24 . C25 . 1.380(6) yes
C24 . H241 . 0.913 no
C25 . H251 . 0.922 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . S1 . C8 . 97.5(2) yes
S1 . C2 . C3 . 119.3(3) yes
S1 . C2 . C7 . 120.1(3) yes
C3 . C2 . C7 . 120.6(4) yes
C2 . C3 . C4 . 119.1(4) yes
C2 . C3 . H31 . 120.1 no
C4 . C3 . H31 . 120.8 no
C3 . C4 . C5 . 121.1(4) yes
C3 . C4 . H41 . 119.3 no
C5 . C4 . H41 . 119.6 no
C4 . C5 . C6 . 119.5(5) yes
C4 . C5 . H51 . 120.9 no
C6 . C5 . H51 . 119.5 no
C5 . C6 . C7 . 120.1(4) yes
C5 . C6 . H61 . 120.6 no
C7 . C6 . H61 . 119.3 no
C6 . C7 . C2 . 119.6(4) yes
C6 . C7 . H71 . 121.4 no
C2 . C7 . H71 . 119.0 no
S1 . C8 . F9 . 112.1(3) yes
S1 . C8 . F10 . 111.3(3) yes
F9 . C8 . F10 . 105.8(3) yes
S1 . C8 . C11 . 113.0(3) yes
F9 . C8 . C11 . 108.0(4) yes
F10 . C8 . C11 . 106.2(3) yes
C8 . C11 . F12 . 109.9(3) yes
C8 . C11 . F13 . 108.9(3) yes
F12 . C11 . F13 . 109.7(3) yes
C8 . C11 . N14 . 111.9(3) yes
F12 . C11 . N14 . 108.1(3) yes
F13 . C11 . N14 . 108.3(3) yes
C11 . N14 . N15 . 121.0(3) yes
C11 . N14 . C18 . 126.5(3) yes
N15 . N14 . C18 . 111.1(3) yes
N14 . N15 . N16 . 106.6(3) yes
N15 . N16 . C17 . 110.4(3) yes
N16 . C17 . C18 . 107.2(4) yes
N16 . C17 . C19 . 121.7(4) yes
C18 . C17 . C19 . 131.1(4) yes
C17 . C18 . N14 . 104.7(4) yes
C17 . C18 . H181 . 129.1 no
N14 . C18 . H181 . 126.2 no
C17 . C19 . C20 . 122.0(4) yes
C17 . C19 . C25 . 120.3(4) yes
C20 . C19 . C25 . 117.7(4) yes
C19 . C20 . C21 . 120.8(4) yes
C19 . C20 . H201 . 119.6 no
C21 . C20 . H201 . 119.6 no
C20 . C21 . C22 . 122.3(4) yes
C20 . C21 . H211 . 118.5 no
C22 . C21 . H211 . 119.1 no
C21 . C22 . C23 . 121.0(4) yes
C21 . C22 . C24 . 117.0(4) yes
C23 . C22 . C24 . 122.0(4) yes
C22 . C23 . H231 . 110.6 no
C22 . C23 . H232 . 110.4 no
H231 . C23 . H232 . 109.3 no
C22 . C23 . H233 . 109.0 no
H231 . C23 . H233 . 108.2 no
H232 . C23 . H233 . 109.3 no
C22 . C24 . C25 . 121.5(4) yes
C22 . C24 . H241 . 119.4 no
C25 . C24 . H241 . 119.0 no
C19 . C25 . C24 . 120.6(4) yes
C19 . C25 . H251 . 119.5 no
C24 . C25 . H251 . 119.8 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 31/03/17 at 14:26:53
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 31/03/17 at 14:26:53
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

