# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_1fcomott
_database_code_depnum_ccdc_archive 'CCDC 1968177'
loop_
_audit_author_name
_audit_author_address
'Luciano Marchio'
;Universita degli studi di Parma
Italy
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-03-23 downloaded from the CCDC.
;
_audit_creation_date             2020-02-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H9 F N4'
_chemical_formula_sum            'C16 H9 F N4'
_chemical_formula_weight         276.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.9020(18)
_cell_length_b                   5.4778(6)
_cell_length_c                   7.3146(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.515(4)
_cell_angle_gamma                90
_cell_volume                     637.13(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    631
_cell_measurement_temperature    190
_cell_measurement_theta_max      23.445
_cell_measurement_theta_min      2.562
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 14592 reflections, Rint = 0.1321
 (4081 with I > 3sig(I), Rint = 0.0841)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1213
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.732
_diffrn_reflns_theta_min         3.934
_diffrn_ambient_temperature      189.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonII'
_diffrn_measurement_method       'omega and phi scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                845
_reflns_number_total             1213
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX3 V2018.1_0'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0845
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²+0.9934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1646
_refine_ls_wR_factor_ref         0.1841
_refine_special_details          
;
The Fluorine atom was refined with a site occupancy factor of 0.5. 
The H atoms on the pyrazole N was disordered in two positions with
site occupancy factors of 0.5.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Others
 Fixed Sof: H1(0.5) H2(0.5) H7(0.5) F1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C8(H8), C7(H7), C1(H1A), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9422(2) 0.0482(6) 0.6810(5) 0.0327(9) Uani 1 1 d . . . . .
H1 H 0.9964 0.0807 0.6758 0.039 Uiso 0.5 1 calc R . P . .
N2 N 0.90878(19) -0.1578(6) 0.7473(5) 0.0305(9) Uani 1 1 d . . . . .
H2 H 0.9371 -0.2830 0.7911 0.037 Uiso 0.5 1 calc R . P . .
C8 C 0.4988(2) 0.7249(7) 0.4111(5) 0.0232(9) Uani 1 1 d . . . . .
H8 H 0.4985 0.8779 0.3499 0.028 Uiso 1 1 calc R . . . .
C7 C 0.5740(2) 0.6136(7) 0.4562(5) 0.0224(9) Uani 1 1 d . . . . .
H7 H 0.6251 0.6932 0.4261 0.027 Uiso 0.5 1 calc R . P A 1
C6 C 0.5774(2) 0.3893(7) 0.5439(5) 0.0207(9) Uani 1 1 d . . . . .
C5 C 0.6564(2) 0.2761(7) 0.5875(5) 0.0247(9) Uani 1 1 d . . . . .
C2 C 0.8038(2) 0.0834(7) 0.6582(5) 0.0253(9) Uani 1 1 d . . . . .
C1 C 0.8813(2) 0.1952(8) 0.6245(6) 0.0314(10) Uani 1 1 d . . . . .
H1A H 0.8889 0.3510 0.5700 0.038 Uiso 1 1 calc R . . . .
C4 C 0.7229(2) 0.1851(8) 0.6199(5) 0.0259(10) Uani 1 1 d . . . . .
C3 C 0.8250(2) -0.1408(8) 0.7356(6) 0.0296(10) Uani 1 1 d . . . . .
H3 H 0.7863 -0.2620 0.7739 0.036 Uiso 1 1 calc R . . . .
F1 F 0.6437(3) 0.7230(9) 0.4116(7) 0.0360(12) Uani 0.5 1 d . . P B 2

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
N1 0.0212(17) 0.031(2) 0.046(2) -0.0038(18) -0.0055(15) 0.0004(16)
N2 0.0189(16) 0.0258(19) 0.047(2) 0.0018(16) -0.0053(14) 0.0039(15)
C8 0.0251(19) 0.023(2) 0.022(2) 0.0009(17) -0.0019(15) 0.0008(17)
C7 0.0172(18) 0.026(2) 0.024(2) -0.0045(17) -0.0025(15) -0.0038(16)
C6 0.0227(19) 0.023(2) 0.0160(19) -0.0030(16) -0.0051(14) 0.0031(16)
C5 0.023(2) 0.029(2) 0.022(2) 0.0008(18) -0.0004(16) -0.0011(18)
C2 0.021(2) 0.030(2) 0.025(2) -0.0004(17) -0.0009(15) 0.0038(17)
C1 0.025(2) 0.028(2) 0.041(3) 0.004(2) -0.0047(18) 0.0051(18)
C4 0.0190(19) 0.032(2) 0.026(2) -0.0009(19) -0.0039(16) 0.0017(18)
C3 0.0172(19) 0.031(2) 0.041(3) 0.001(2) -0.0039(16) 0.0017(18)
F1 0.024(2) 0.036(3) 0.048(3) 0.001(2) -0.001(2) -0.009(2)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1 0.8800 . ?
N1 N2 1.340(5) . ?
N1 C1 1.323(5) . ?
N2 H2 0.8800 . ?
N2 C3 1.337(5) . ?
C8 H8 0.9500 . ?
C8 C7 1.380(5) . ?
C8 C6 1.405(5) 3_666 ?
C7 H7 0.9500 . ?
C7 C6 1.387(5) . ?
C7 F1 1.305(5) . ?
C6 C8 1.405(5) 3_666 ?
C6 C5 1.434(5) . ?
C5 C4 1.192(5) . ?
C2 C1 1.400(5) . ?
C2 C4 1.427(5) . ?
C2 C3 1.392(6) . ?
C1 H1A 0.9500 . ?
C3 H3 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 H1 125.3 . . ?
C1 N1 H1 125.3 . . ?
C1 N1 N2 109.5(3) . . ?
N1 N2 H2 125.8 . . ?
C3 N2 N1 108.5(3) . . ?
C3 N2 H2 125.8 . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C6 119.6(4) . 3_666 ?
C6 C8 H8 120.2 3_666 . ?
C8 C7 H7 118.9 . . ?
C8 C7 C6 122.2(3) . . ?
C6 C7 H7 118.9 . . ?
F1 C7 C8 118.3(4) . . ?
F1 C7 C6 119.5(4) . . ?
C8 C6 C5 120.7(3) 3_666 . ?
C7 C6 C8 118.2(3) . 3_666 ?
C7 C6 C5 121.1(3) . . ?
C4 C5 C6 178.3(4) . . ?
C1 C2 C4 126.0(4) . . ?
C3 C2 C1 104.3(3) . . ?
C3 C2 C4 129.7(4) . . ?
N1 C1 C2 108.8(4) . . ?
N1 C1 H1A 125.6 . . ?
C2 C1 H1A 125.6 . . ?
C5 C4 C2 178.2(4) . . ?
N2 C3 C2 109.0(4) . . ?
N2 C3 H3 125.5 . . ?
C2 C3 H3 125.5 . . ?

_iucr_refine_instructions_details 
;

    1fcomott.res created by SHELXL-2014/7

TITL 1fcomott_0m_4_a.res in P2(1)/c
REM Old TITL 1Fcomott_0m_4 in P21/a #14
REM SHELXT solution in P2(1)/c
REM R1 0.189, Rweak 0.038, Alpha 0.054, Orientation a'=c, b'=-b, c'=a
REM Formula found by SHELXT: C9 N2
CELL 0.71073 15.902 5.4778 7.3146 90 90.515 90
ZERR 2 0.0018 0.0006 0.001 0 0.004 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H F N
UNIT 32 18 2 8
 
L.S. 4 0 0
PLAN  20
TEMP -83.16
BOND $H
list 4
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\1fcomott.hkl">
REM </olex2.extras>
 
WGHT    0.049100    0.993400
FVAR       0.72845
N1    4    0.942237    0.048214    0.680994    11.00000    0.02117    0.03101 =
         0.04594   -0.00377   -0.00545    0.00036
AFIX  43
H1    2    0.996360    0.080700    0.675840    10.50000   -1.20000
AFIX   0
N2    4    0.908783   -0.157765    0.747298    11.00000    0.01890    0.02577 =
         0.04681    0.00182   -0.00530    0.00391
AFIX  43
H2    2    0.937145   -0.283036    0.791114    10.50000   -1.20000
AFIX   0
C8    1    0.498766    0.724936    0.411078    11.00000    0.02505    0.02275 =
         0.02168    0.00090   -0.00191    0.00081
AFIX  43
H8    2    0.498480    0.877947    0.349939    11.00000   -1.20000
AFIX   0
C7    1    0.573986    0.613581    0.456155    11.00000    0.01719    0.02589 =
         0.02393   -0.00455   -0.00252   -0.00381
PART 1
AFIX  43
H7    2    0.625111    0.693171    0.426116    10.50000   -1.20000
AFIX   0
PART 0
C6    1    0.577392    0.389319    0.543861    11.00000    0.02267    0.02335 =
         0.01598   -0.00300   -0.00509    0.00307
C5    1    0.656372    0.276073    0.587490    11.00000    0.02290    0.02876 =
         0.02230    0.00080   -0.00042   -0.00111
C2    1    0.803819    0.083404    0.658229    11.00000    0.02126    0.02984 =
         0.02464   -0.00044   -0.00093    0.00385
C1    1    0.881294    0.195207    0.624470    11.00000    0.02451    0.02834 =
         0.04138    0.00353   -0.00473    0.00514
AFIX  43
H1A   2    0.888877    0.350976    0.569952    11.00000   -1.20000
AFIX   0
C4    1    0.722930    0.185073    0.619912    11.00000    0.01902    0.03201 =
         0.02649   -0.00095   -0.00385    0.00174
C3    1    0.825014   -0.140763    0.735622    11.00000    0.01719    0.03089 =
         0.04066    0.00102   -0.00394    0.00166
AFIX  43
H3    2    0.786252   -0.261987    0.773925    11.00000   -1.20000
AFIX   0
PART 2
F1    3    0.643748    0.723030    0.411637    10.50000    0.02375    0.03641 =
         0.04776    0.00074   -0.00058   -0.00897
HKLF 5
 
REM  1fcomott_0m_4_a.res in P2(1)/c
REM R1 =  0.0845 for     845 Fo > 4sig(Fo)  and  0.1246 for all    1213 data
REM    100 parameters refined using      0 restraints
 
END  
     
WGHT      0.0345      0.9563 

REM Highest difference peak  0.333,  deepest hole -0.331,  1-sigma level  0.071
Q1    1   0.8605  0.6256  0.5803  11.00000  0.05    0.33
Q2    1   0.9513 -0.2950  0.7308  11.00000  0.05    0.31
Q3    1   0.5406  0.3808  0.6317  11.00000  0.05    0.29
Q4    1   0.8993 -0.1566  0.5368  11.00000  0.05    0.29
Q5    1   0.5779  0.5424  0.5756  11.00000  0.05    0.27
Q6    1   0.5227  0.5651  0.4029  11.00000  0.05    0.26
Q7    1   0.9572 -0.1607  0.8643  11.00000  0.05    0.25
Q8    1   0.7776  0.1932  0.6815  11.00000  0.05    0.23
Q9    1   1.0004  0.0540  0.7259  11.00000  0.05    0.23
Q10   1   0.9051  0.2043  0.7833  11.00000  0.05    0.22
Q11   1   0.7038  0.3409  0.3733  11.00000  0.05    0.22
Q12   1   0.8002 -0.0729  0.6439  11.00000  0.05    0.21
Q13   1   0.7050  0.0547  0.3570  11.00000  0.05    0.21
Q14   1   0.6133  0.0230  0.5864  11.00000  0.05    0.21
Q15   1   0.6199  0.2017  0.6797  11.00000  0.05    0.21
Q16   1   0.6838  0.1773  0.6711  11.00000  0.05    0.21
Q17   1   0.9668  0.4809  0.4963  11.00000  0.05    0.21
Q18   1   0.6225  0.4021  0.5766  11.00000  0.05    0.21
Q19   1   0.6985  0.2996  0.5379  11.00000  0.05    0.20
Q20   1   0.7986 -0.2926  0.8622  11.00000  0.05    0.20

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0845 for 845 Fo > 4sig(Fo) and 0.1246 for all 1348 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.33, deepest hole -0.33
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.1246
  REM R1_gt = 0.0845
  REM wR_ref = 0.1841
  REM GOOF = 1.072
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 1348
  REM Reflections_gt = 845
  REM Parameters = n/a
  REM Hole = -0.33
  REM Peak = 0.33
  REM Flack = n/a

  
;
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_4fcomott_0m
_database_code_depnum_ccdc_archive 'CCDC 1968179'
loop_
_audit_author_name
_audit_author_address
'Luciano Marchio'
;Universita degli studi di Parma
Italy
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-03-23 downloaded from the CCDC.
;
_audit_creation_date             2018-10-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H6 F4 N4'
_chemical_formula_sum            'C16 H6 F4 N4'
_chemical_formula_weight         330.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.3901(6)
_cell_length_b                   6.3395(3)
_cell_length_c                   7.8929(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.316(2)
_cell_angle_gamma                90
_cell_volume                     668.88(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5245
_cell_measurement_temperature    190
_cell_measurement_theta_max      25.658
_cell_measurement_theta_min      3.047
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0743 before and 0.0554 after correction.
The Ratio of minimum to maximum transmission is 0.9589.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15225
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.739
_diffrn_reflns_theta_min         3.557
_diffrn_ambient_temperature      190
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonII'
_diffrn_measurement_method       'omega and phi scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1102
_reflns_number_total             1269
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX3 V2018.1_0'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0920P)²+0.2652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1449
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C1(H1A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.69419(9) 0.49049(17) 0.42031(17) 0.0346(4) Uani 1 1 d . . . . .
F2 F 0.55011(10) 0.48332(18) 0.17223(16) 0.0353(4) Uani 1 1 d . . . . .
N1 N 0.93564(12) 0.6370(3) 1.1450(2) 0.0321(5) Uani 1 1 d . . . . .
N2 N 0.92007(13) 0.4377(3) 1.1974(2) 0.0356(5) Uani 1 1 d . . . . .
C6 C 0.57686(15) 0.5064(3) 0.6315(3) 0.0270(5) Uani 1 1 d . . . . .
C7 C 0.59798(15) 0.4965(3) 0.4623(3) 0.0258(5) Uani 1 1 d . . . . .
C8 C 0.52435(16) 0.4909(3) 0.3336(3) 0.0263(5) Uani 1 1 d . . . . .
C2 C 0.80378(14) 0.5292(3) 0.9921(2) 0.0267(5) Uani 1 1 d . . . . .
C5 C 0.65426(16) 0.5135(3) 0.7632(3) 0.0290(5) Uani 1 1 d . . . . .
C4 C 0.72206(15) 0.5196(3) 0.8690(3) 0.0277(5) Uani 1 1 d . . . . .
C3 C 0.84023(15) 0.3730(4) 1.1042(3) 0.0346(5) Uani 1 1 d . . . . .
H3 H 0.8113 0.2368 1.1128 0.041 Uiso 1 1 calc R . . . .
C1 C 0.86825(14) 0.6986(3) 1.0240(2) 0.0314(5) Uani 1 1 d . . . . .
H1A H 0.8649 0.8325 0.9699 0.038 Uiso 1 1 calc R . . . .
H1 H 0.990(2) 0.732(5) 1.193(4) 0.064(8) Uiso 1 1 d . . . . .

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 0.0217(7) 0.0384(8) 0.0424(8) -0.0004(5) -0.0098(5) 0.0002(4)
F2 0.0376(7) 0.0397(8) 0.0273(7) -0.0011(5) -0.0101(5) 0.0015(5)
N1 0.0233(8) 0.0413(11) 0.0304(9) -0.0046(7) -0.0094(7) -0.0020(7)
N2 0.0248(9) 0.0472(11) 0.0330(9) 0.0067(8) -0.0133(7) -0.0010(8)
C6 0.0264(11) 0.0200(10) 0.0322(11) -0.0010(7) -0.0187(9) 0.0001(7)
C7 0.0220(10) 0.0201(9) 0.0339(11) 0.0003(7) -0.0113(8) -0.0001(7)
C8 0.0283(11) 0.0205(10) 0.0288(11) -0.0008(7) -0.0111(8) 0.0003(7)
C2 0.0193(9) 0.0377(11) 0.0220(10) -0.0027(7) -0.0084(7) 0.0019(7)
C5 0.0269(11) 0.0257(10) 0.0325(11) -0.0009(7) -0.0151(9) 0.0012(7)
C4 0.0241(10) 0.0320(11) 0.0256(10) -0.0022(7) -0.0097(8) 0.0009(7)
C3 0.0272(10) 0.0396(12) 0.0352(11) 0.0047(9) -0.0132(8) -0.0018(9)
C1 0.0270(10) 0.0376(11) 0.0285(10) -0.0010(8) -0.0076(8) 0.0019(8)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C7 1.349(2) . ?
F2 C8 1.339(3) . ?
N1 N2 1.350(3) . ?
N1 C1 1.334(2) . ?
N1 H1 1.00(3) . ?
N2 C3 1.327(3) . ?
C6 C7 1.382(3) . ?
C6 C8 1.399(3) 3_666 ?
C6 C5 1.426(3) . ?
C7 C8 1.375(3) . ?
C8 C6 1.399(3) 3_666 ?
C2 C4 1.422(3) . ?
C2 C3 1.397(3) . ?
C2 C1 1.392(3) . ?
C5 C4 1.198(3) . ?
C3 H3 0.9500 . ?
C1 H1A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 H1 124.5(16) . . ?
C1 N1 N2 112.55(16) . . ?
C1 N1 H1 122.9(16) . . ?
C3 N2 N1 104.68(16) . . ?
C7 C6 C8 116.47(19) . 3_666 ?
C7 C6 C5 121.7(2) . . ?
C8 C6 C5 121.8(2) 3_666 . ?
F1 C7 C6 119.36(18) . . ?
F1 C7 C8 118.2(2) . . ?
C8 C7 C6 122.5(2) . . ?
F2 C8 C6 119.59(18) . 3_666 ?
F2 C8 C7 119.4(2) . . ?
C7 C8 C6 121.0(2) . 3_666 ?
C3 C2 C4 129.01(18) . . ?
C1 C2 C4 126.97(18) . . ?
C1 C2 C3 104.00(17) . . ?
C4 C5 C6 177.4(2) . . ?
C5 C4 C2 178.8(2) . . ?
N2 C3 C2 111.89(19) . . ?
N2 C3 H3 124.1 . . ?
C2 C3 H3 124.1 . . ?
N1 C1 C2 106.89(18) . . ?
N1 C1 H1A 126.6 . . ?
C2 C1 H1A 126.6 . . ?

_iucr_refine_instructions_details 
;

    4fcomott_0m.res created by SHELXL-2014/7

TITL 4fcomott_0m_a.res in P2(1)/c
REM Old TITL 4Fcomott_0m in P2/a #13
REM SHELXT solution in P2(1)/c
REM R1 0.144, Rweak 0.006, Alpha 0.027, Orientation a'=c, b'=-b, c'=a
REM Formula found by SHELXT: C9 N F2
CELL 0.71073 13.3901 6.3395 7.8929 90 93.316 90
ZERR 2 0.0006 0.0003 0.0003 0 0.002 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H F N
UNIT 32 12 8 8
 
L.S. 4 0 0
PLAN  20
SIZE 0.05 0.03 0.03
TEMP -83.15
BOND $H
list 4
fmap 2 53
acta
OMIT -6 0 6
OMIT -9 3 3
OMIT 3 6 0
OMIT -2 3 1
OMIT -2 1 3
OMIT -9 0 6
OMIT -3 3 3
REM <olex2.extras>
REM <HklSrc "%.\\4Fcomott_0m.hkl">
REM </olex2.extras>
 
WGHT    0.092000    0.265200
FVAR       0.65648
F1    3    0.694187    0.490487    0.420310    11.00000    0.02167    0.03839 =
         0.04237   -0.00038   -0.00980    0.00018
F2    3    0.550112    0.483324    0.172226    11.00000    0.03763    0.03967 =
         0.02733   -0.00108   -0.01012    0.00149
N1    4    0.935643    0.637014    1.145037    11.00000    0.02334    0.04127 =
         0.03040   -0.00460   -0.00945   -0.00202
N2    4    0.920070    0.437693    1.197441    11.00000    0.02482    0.04720 =
         0.03302    0.00669   -0.01331   -0.00097
C6    1    0.576863    0.506443    0.631471    11.00000    0.02637    0.01996 =
         0.03221   -0.00105   -0.01867    0.00010
C7    1    0.597981    0.496475    0.462317    11.00000    0.02198    0.02008 =
         0.03386    0.00033   -0.01128   -0.00013
C8    1    0.524346    0.490936    0.333580    11.00000    0.02828    0.02045 =
         0.02880   -0.00082   -0.01109    0.00027
C2    1    0.803778    0.529176    0.992073    11.00000    0.01932    0.03773 =
         0.02201   -0.00274   -0.00843    0.00192
C5    1    0.654264    0.513494    0.763239    11.00000    0.02692    0.02569 =
         0.03250   -0.00094   -0.01512    0.00115
C4    1    0.722065    0.519602    0.869014    11.00000    0.02409    0.03201 =
         0.02564   -0.00217   -0.00966    0.00089
C3    1    0.840231    0.372978    1.104244    11.00000    0.02718    0.03956 =
         0.03517    0.00474   -0.01324   -0.00181
AFIX  43
H3    2    0.811333    0.236805    1.112767    11.00000   -1.20000
AFIX   0
C1    1    0.868253    0.698613    1.023993    11.00000    0.02701    0.03764 =
         0.02846   -0.00096   -0.00760    0.00192
AFIX  43
H1A   2    0.864910    0.832515    0.969924    11.00000   -1.20000
AFIX   0
H1    2    0.989772    0.731544    1.193194    11.00000    0.06432
HKLF 4
 
REM  4fcomott_0m_a.res in P2(1)/c
REM R1 =  0.0508 for    1102 Fo > 4sig(Fo)  and  0.0570 for all    1269 data
REM    113 parameters refined using      0 restraints
 
END  
     
WGHT      0.0867      0.2592 

REM Highest difference peak  0.462,  deepest hole -0.251,  1-sigma level  0.070
Q1    1   0.8715  0.2908  1.0160  11.00000  0.05    0.46
Q2    1   0.9338  0.3409  1.1285  11.00000  0.05    0.42
Q3    1   0.5281  0.5021  0.6448  11.00000  0.05    0.41
Q4    1   0.8363  0.6258  1.1118  11.00000  0.05    0.36
Q5    1   0.9055  0.5820  1.2224  11.00000  0.05    0.31
Q6    1   0.5811  0.5461  0.5497  11.00000  0.05    0.31
Q7    1   0.5812  0.4598  0.5605  11.00000  0.05    0.29
Q8    1   0.9137  0.5419  1.2027  11.00000  0.05    0.28
Q9    1   0.6332  0.5016  0.4346  11.00000  0.05    0.28
Q10   1   0.8235  0.4326  1.0137  11.00000  0.05    0.27
Q11   1   0.6121  0.5024  0.6899  11.00000  0.05    0.26
Q12   1   0.6740  0.4817  0.8721  11.00000  0.05    0.25
Q13   1   0.5640  0.5117  0.3909  11.00000  0.05    0.24
Q14   1   0.5433  0.5027  0.2649  11.00000  0.05    0.23
Q15   1   0.7999  0.4532  1.0636  11.00000  0.05    0.23
Q16   1   0.7030  0.4598  0.7874  11.00000  0.05    0.20
Q17   1   0.7135  0.5151  0.7821  11.00000  0.05    0.19
Q18   1   0.7602  0.5199  0.9482  11.00000  0.05    0.19
Q19   1   0.9227  0.3961  1.2967  11.00000  0.05    0.12
Q20   1   0.7605  0.6419  1.1243  11.00000  0.05    0.12

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0508 for 1102 Fo > 4sig(Fo) and 0.0570 for all 16183 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.46, deepest hole -0.25
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0570
  REM R1_gt = 0.0508
  REM wR_ref = 0.1449
  REM GOOF = 1.069
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 16183
  REM Reflections_gt = 1102
  REM Parameters = n/a
  REM Hole = -0.25
  REM Peak = 0.46
  REM Flack = n/a

  
;
_olex2_exptl_crystal_mounting_method cryoloop
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2fcomott_0m
_database_code_depnum_ccdc_archive 'CCDC 1968178'
loop_
_audit_author_name
_audit_author_address
'Luciano Marchio'
;Universita degli studi di Parma
Italy
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-03-23 downloaded from the CCDC.
;
_audit_creation_date             2020-02-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H8 F2 N4'
_chemical_formula_sum            'C16 H8 F2 N4'
_chemical_formula_weight         294.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.913(6)
_cell_length_b                   5.411(3)
_cell_length_c                   15.519(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.200(13)
_cell_angle_gamma                90
_cell_volume                     649.5(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2948
_cell_measurement_temperature    190
_cell_measurement_theta_max      25.410
_cell_measurement_theta_min      2.635
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0741 before and 0.0604 after correction.
The Ratio of minimum to maximum transmission is 0.9132.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13572
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.820
_diffrn_reflns_theta_min         2.686
_diffrn_ambient_temperature      190.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonII'
_diffrn_measurement_method       'omega and phi scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   microfocus
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1014
_reflns_number_total             1247
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX3 V2018.1_0'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1247
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+0.2856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1092
_refine_special_details          
;
The F1 and F2 fluorine atoms and the C4 and C5 atoms 
were refined with site occupancy factors of 0.5. 
Hence, the alkynyl group and the fluorinated aromatic 
ring were found disordered in two positions.
;

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 C7-F1 = C8-F2
 1.34 with sigma of 0.02
 C7A-C6A = C7-C6 = C8A-C7A = C8-C7
 1.39 with sigma of 0.02
 C5A-C4A = C5-C4
 1.15 with sigma of 0.02
3. Restrained planarity
 C6A, C7, F1, C8, F2
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C6) = Uanis(C6A)
Uanis(C4A) = Uanis(C5A)
Uanis(C4) = Uanis(C5)
5. Others
 Fixed Sof: F1(0.5) C4A(0.5) C6A(0.5) C7A(0.5) H7A(0.5) C5(0.5) F2(0.5)
 C8A(0.5) H8A(0.5) C7(0.5) C8(0.5) C6(0.5) C5A(0.5) C4(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C3(H3), C7A(H7A), C8A(H8A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.17391(18) 0.6819(3) 0.29624(10) 0.0287(4) Uani 1 1 d . . . . .
H1 H 0.1040 0.8090 0.2949 0.034 Uiso 1 1 calc R . . . .
F1 F 1.0091(3) 0.3890(5) 0.41363(18) 0.0391(6) Uani 0.5 1 d D . P A -1
N2 N 0.13339(18) 0.4771(3) 0.24627(10) 0.0301(4) Uani 1 1 d . . . . .
C2 C 0.4008(2) 0.4441(3) 0.33177(12) 0.0283(4) Uani 1 1 d . . . . .
C1 C 0.3321(2) 0.6698(3) 0.34792(13) 0.0311(4) Uani 1 1 d . . . . .
H1A H 0.3867 0.7927 0.3880 0.037 Uiso 1 1 calc R . . . .
C3 C 0.2715(2) 0.3336(3) 0.26806(13) 0.0305(4) Uani 1 1 d . . . . .
H3 H 0.2815 0.1749 0.2434 0.037 Uiso 1 1 calc R . . . .
C4A C 0.5513(18) 0.331(2) 0.3814(8) 0.0267(17) Uani 0.5 1 d D . P A -1
C6A C 0.8673(13) 0.1495(17) 0.4504(7) 0.0200(13) Uani 0.5 1 d D . P A 1
C7A C 1.0281(14) 0.2442(14) 0.4487(6) 0.0220(16) Uani 0.5 1 d D . P A 1
H7A H 1.0369 0.3933 0.4177 0.026 Uiso 0.5 1 calc R . P A 1
C5 C 0.7089(13) 0.2614(16) 0.4040(6) 0.0269(17) Uani 0.5 1 d D . P A 1
F2 F 1.2955(4) 0.1628(4) 0.49664(17) 0.0413(6) Uani 0.5 1 d D . P A -1
C8A C 1.1771(10) 0.1253(19) 0.4916(7) 0.0238(16) Uani 0.5 1 d D . P A 1
H8A H 1.2904 0.1818 0.4908 0.029 Uiso 0.5 1 calc R . P A 1
C7 C 0.9917(13) 0.1806(17) 0.4588(7) 0.027(2) Uani 0.5 1 d D . P A -1
C8 C 1.1401(15) 0.0642(17) 0.5023(7) 0.0265(19) Uani 0.5 1 d D . P A -1
C6 C 0.8292(12) 0.0925(18) 0.4613(7) 0.0200(13) Uani 0.5 1 d D . P A -1
C5A C 0.6779(13) 0.2222(16) 0.4175(6) 0.0267(17) Uani 0.5 1 d D . P A -1
C4 C 0.5727(18) 0.346(3) 0.3678(8) 0.0269(17) Uani 0.5 1 d D . P A 1

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
N1 0.0190(7) 0.0242(8) 0.0404(9) 0.0026(7) 0.0007(6) 0.0027(6)
F1 0.0356(13) 0.0334(14) 0.0473(15) 0.0150(12) 0.0069(11) -0.0001(10)
N2 0.0221(7) 0.0293(8) 0.0361(9) 0.0041(7) 0.0001(6) -0.0031(6)
C2 0.0222(9) 0.0283(9) 0.0327(10) 0.0052(8) 0.0020(7) 0.0028(7)
C1 0.0211(9) 0.0308(10) 0.0376(11) -0.0029(8) -0.0028(8) 0.0002(7)
C3 0.0277(9) 0.0246(9) 0.0370(11) 0.0033(8) 0.0020(8) 0.0005(8)
C4A 0.023(3) 0.036(3) 0.023(3) 0.003(2) 0.011(2) 0.0065(19)
C6A 0.010(4) 0.027(4) 0.024(2) 0.000(2) 0.0055(19) -0.002(2)
C7A 0.022(3) 0.020(5) 0.023(3) 0.008(3) 0.002(2) 0.000(3)
C5 0.023(3) 0.038(3) 0.022(3) 0.004(2) 0.008(2) 0.005(2)
F2 0.0219(14) 0.0443(14) 0.0571(17) 0.0108(11) 0.0066(11) -0.0032(11)
C8A 0.011(5) 0.030(4) 0.031(3) 0.002(3) 0.005(3) -0.003(3)
C7 0.035(7) 0.016(4) 0.031(3) 0.005(3) 0.010(3) -0.003(3)
C8 0.016(4) 0.032(5) 0.033(4) -0.001(4) 0.008(2) -0.009(3)
C6 0.010(4) 0.027(4) 0.024(2) 0.000(2) 0.0055(19) -0.002(2)
C5A 0.023(3) 0.036(3) 0.023(3) 0.003(2) 0.011(2) 0.0065(19)
C4 0.023(3) 0.038(3) 0.022(3) 0.004(2) 0.008(2) 0.005(2)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1 0.8800 . ?
N1 N2 1.352(2) . ?
N1 C1 1.338(2) . ?
F1 C6A 1.880(6) . ?
F1 C7A 0.948(8) . ?
F1 C7 1.350(8) . ?
N2 C3 1.325(2) . ?
C2 C1 1.381(3) . ?
C2 C3 1.398(3) . ?
C2 C4A 1.413(15) . ?
C2 C4 1.457(14) . ?
C1 H1A 0.9500 . ?
C3 H3 0.9500 . ?
C4A C5 1.28(2) . ?
C4A C5A 1.195(7) . ?
C6A C7A 1.377(8) . ?
C6A C5 1.440(16) . ?
C6A C8A 1.811(13) 3_756 ?
C6A C7 0.979(16) . ?
C6A C5A 1.529(16) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.384(11) . ?
C7A C8 1.454(18) . ?
C7A C6 1.821(11) . ?
C5 C6 1.475(16) . ?
C5 C4 1.196(7) . ?
F2 C8A 0.946(8) . ?
F2 C8 1.360(7) . ?
C8A C6A 1.811(13) 3_756 ?
C8A H8A 0.9500 . ?
C8A C7 1.478(17) . ?
C7 C8 1.377(12) . ?
C7 C6 1.379(8) . ?
C6 C5A 1.430(16) . ?
C5A C4 1.21(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 H1 123.8 . . ?
C1 N1 H1 123.8 . . ?
C1 N1 N2 112.47(15) . . ?
C7A F1 C6A 44.6(6) . . ?
C7A F1 C7 14.6(10) . . ?
C7 F1 C6A 30.0(7) . . ?
C3 N2 N1 104.55(15) . . ?
C1 C2 C3 104.44(16) . . ?
C1 C2 C4A 127.0(5) . . ?
C1 C2 C4 128.7(5) . . ?
C3 C2 C4A 127.4(6) . . ?
C3 C2 C4 126.8(5) . . ?
C4A C2 C4 12.2(9) . . ?
N1 C1 C2 106.79(16) . . ?
N1 C1 H1A 126.6 . . ?
C2 C1 H1A 126.6 . . ?
N2 C3 C2 111.76(17) . . ?
N2 C3 H3 124.1 . . ?
C2 C3 H3 124.1 . . ?
C5 C4A C2 159.7(13) . . ?
C5A C4A C2 174.4(8) . . ?
C5A C4A C5 18.8(6) . . ?
C7A C6A F1 28.9(4) . . ?
C7A C6A C5 123.0(8) . . ?
C7A C6A C8A 126.3(9) . 3_756 ?
C7A C6A C5A 137.9(8) . . ?
C5 C6A F1 94.1(6) . . ?
C5 C6A C8A 110.7(7) . 3_756 ?
C5 C6A C5A 15.6(5) . . ?
C8A C6A F1 155.2(9) 3_756 . ?
C7 C6A F1 43.5(6) . . ?
C7 C6A C7A 14.6(8) . . ?
C7 C6A C5 137.6(9) . . ?
C7 C6A C8A 111.7(13) . 3_756 ?
C7 C6A C5A 152.4(10) . . ?
C5A C6A F1 109.1(7) . . ?
C5A C6A C8A 95.6(6) . 3_756 ?
F1 C7A C6A 106.5(10) . . ?
F1 C7A H7A 13.1 . . ?
F1 C7A C8A 132.5(10) . . ?
F1 C7A C8 152.3(12) . . ?
F1 C7A C6 113.5(11) . . ?
C6A C7A H7A 119.5 . . ?
C6A C7A C8A 121.0(7) . . ?
C6A C7A C8 101.2(7) . . ?
C6A C7A C6 7.1(8) . . ?
C8A C7A H7A 119.5 . . ?
C8A C7A C8 19.8(3) . . ?
C8A C7A C6 114.0(6) . . ?
C8 C7A H7A 139.3 . . ?
C8 C7A C6 94.2(6) . . ?
C6 C7A H7A 126.5 . . ?
C4A C5 C6A 163.0(11) . . ?
C4A C5 C6 144.8(11) . . ?
C6A C5 C6 19.2(3) . . ?
C4 C5 C4A 13.8(10) . . ?
C4 C5 C6A 176.5(5) . . ?
C4 C5 C6 157.4(5) . . ?
C8A F2 C8 13.5(11) . . ?
C6A C8A H8A 123.7 3_756 . ?
C7A C8A C6A 112.7(6) . 3_756 ?
C7A C8A H8A 123.7 . . ?
C7A C8A C7 19.5(3) . . ?
F2 C8A C6A 115.4(11) . 3_756 ?
F2 C8A C7A 131.9(11) . . ?
F2 C8A H8A 8.3 . . ?
F2 C8A C7 151.5(12) . . ?
C7 C8A C6A 93.1(6) . 3_756 ?
C7 C8A H8A 143.2 . . ?
F1 C7 C8A 98.4(6) . . ?
F1 C7 C8 117.8(6) . . ?
F1 C7 C6 120.1(8) . . ?
C6A C7 F1 106.5(12) . . ?
C6A C7 C8A 155.1(13) . . ?
C6A C7 C8 135.7(10) . . ?
C6A C7 C6 13.7(10) . . ?
C8 C7 C8A 19.5(4) . . ?
C8 C7 C6 122.1(8) . . ?
C6 C7 C8A 141.6(9) . . ?
F2 C8 C7A 98.7(6) . . ?
F2 C8 C7 118.6(6) . . ?
C7 C8 C7A 19.9(4) . . ?
C5 C6 C7A 96.8(6) . . ?
C7 C6 C7A 8.0(7) . . ?
C7 C6 C5 104.8(7) . . ?
C7 C6 C5A 120.6(7) . . ?
C5A C6 C7A 112.5(7) . . ?
C5A C6 C5 16.2(6) . . ?
C4A C5A C6A 161.6(5) . . ?
C4A C5A C6 179.5(7) . . ?
C4A C5A C4 14.7(11) . . ?
C6 C5A C6A 18.5(4) . . ?
C4 C5A C6A 148.1(12) . . ?
C4 C5A C6 165.7(12) . . ?
C5 C4 C2 174.3(6) . . ?
C5 C4 C5A 19.7(7) . . ?
C5A C4 C2 155.1(13) . . ?

_iucr_refine_instructions_details 
;

    2fcomott_0m.res created by SHELXL-2014/7

TITL 2Fcomott_0m_a.res in P2(1)/c
REM <autosolution>
REM {'C005': 'AtomInfo(hybridisation=3)',
REM 'C004': 'AtomInfo(hybridisation=3)',
REM 'C007': 'AtomInfo(hybridisation=3)',
REM 'C006': 'AtomInfo(hybridisation=3)',
REM 'N008': 'AtomInfo(hybridisation=3)',
REM 'C003': 'AtomInfo(hybridisation=3)',
REM 'C009': 'AtomInfo(hybridisation=3)',
REM 'N002': 'AtomInfo(hybridisation=3)',
REM 'N001': 'AtomInfo(hybridisation=3)',
REM 'C00C': 'AtomInfo(hybridisation=3)',
REM 'C00B': 'AtomInfo(hybridisation=3)',
REM 'N00A': 'AtomInfo(hybridisation=3)'}
REM </autosolution>
CELL 0.71073 7.9127 5.4114 15.5187 90 102.2 90
ZERR 2 0.0058 0.0026 0.0107 0 0.013 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H F N
UNIT 32 16 4 8
DFIX 1.34 C7 F1 C8 F2
DFIX 1.39 C7A C6A C7 C6 C8A C7A C8 C7
DFIX 1.15 C5A C4A C5 C4
FLAT C6A C7 F1 C8 F2
EADP C6 C6A
EADP C4A C5A
EADP C4 C5
 
L.S. 6
PLAN  -15 0 0
SIZE 0.1 0.05 0.02
TEMP -83.15
BOND $H
fmap 2
acta
OMIT 1 0 0
OMIT 3 0 0
OMIT -3 0 12
OMIT 2 1 0
REM <olex2.extras>
REM <HklSrc "%.\\2Fcomott_0m.hkl">
REM </olex2.extras>
 
WGHT    0.047300    0.285600
FVAR       0.84185
N1    4    0.173907    0.681900    0.296242    11.00000    0.01904    0.02419 =
         0.04045    0.00263    0.00069    0.00270
AFIX  43
H1    2    0.104035    0.809003    0.294927    11.00000   -1.20000
AFIX   0
PART -1
F1    3    1.009073    0.389015    0.413625    10.50000    0.03561    0.03345 =
         0.04730    0.01499    0.00689   -0.00007
PART 0
N2    4    0.133392    0.477101    0.246271    11.00000    0.02213    0.02930 =
         0.03614    0.00413    0.00005   -0.00309
C2    1    0.400802    0.444059    0.331774    11.00000    0.02216    0.02827 =
         0.03271    0.00524    0.00204    0.00285
C1    1    0.332096    0.669782    0.347921    11.00000    0.02107    0.03075 =
         0.03763   -0.00293   -0.00280    0.00018
AFIX  43
H1A   2    0.386658    0.792739    0.388002    11.00000   -1.20000
AFIX   0
C3    1    0.271531    0.333579    0.268061    11.00000    0.02766    0.02462 =
         0.03701    0.00332    0.00197    0.00052
AFIX  43
H3    2    0.281490    0.174942    0.243389    11.00000   -1.20000
AFIX   0
PART -1
C4A   1    0.551315    0.331324    0.381433    10.50000    0.02346    0.03647 =
         0.02288    0.00329    0.01094    0.00647
PART 0
PART 1
C6A   1    0.867324    0.149526    0.450401    10.50000    0.01033    0.02705 =
         0.02352    0.00045    0.00547   -0.00234
C7A   1    1.028071    0.244192    0.448740    10.50000    0.02196    0.02025 =
         0.02262    0.00772    0.00232   -0.00016
AFIX  43
H7A   2    1.036854    0.393318    0.417683    10.50000   -1.20000
AFIX   0
C5    1    0.708860    0.261385    0.404042    10.50000    0.02253    0.03752 =
         0.02207    0.00406    0.00812    0.00542
PART 0
PART -1
F2    3    1.295489    0.162796    0.496639    10.50000    0.02188    0.04433 =
         0.05708    0.01080    0.00662   -0.00323
PART 0
PART 1
C8A   1    1.177099    0.125330    0.491648    10.50000    0.01086    0.02969 =
         0.03112    0.00181    0.00498   -0.00346
AFIX  43
H8A   2    1.290401    0.181835    0.490785    10.50000   -1.20000
AFIX   0
PART 0
PART -1
C7    1    0.991674    0.180551    0.458784    10.50000    0.03529    0.01581 =
         0.03068    0.00492    0.00959   -0.00288
C8    1    1.140065    0.064249    0.502307    10.50000    0.01611    0.03167 =
         0.03298   -0.00096    0.00828   -0.00858
C6    1    0.829218    0.092491    0.461318    10.50000    0.01033    0.02705 =
         0.02352    0.00045    0.00547   -0.00234
C5A   1    0.677944    0.222226    0.417499    10.50000    0.02346    0.03647 =
         0.02288    0.00329    0.01094    0.00647
PART 0
PART 1
C4    1    0.572656    0.345645    0.367777    10.50000    0.02253    0.03752 =
         0.02207    0.00406    0.00812    0.00542
HKLF 4
 
REM  2Fcomott_0m_a.res in P2(1)/c
REM R1 =  0.0447 for    1014 Fo > 4sig(Fo)  and  0.0604 for all    1247 data
REM    136 parameters refined using     10 restraints
 
END  
     
WGHT      0.0418      0.2667 

REM Highest difference peak  0.185,  deepest hole -0.181,  1-sigma level  0.039
Q1    1   0.3633  0.4168  0.2854  11.00000  0.05    0.18
Q2    1   0.3893  0.5480  0.3418  11.00000  0.05    0.16
Q3    1   0.0708  0.4476  0.1797  11.00000  0.05    0.15
Q4    1   0.6306  0.2291  0.3617  11.00000  0.05    0.14
Q5    1   0.1867  0.3360  0.2851  11.00000  0.05    0.13
Q6    1   0.0380  0.3670  0.2544  11.00000  0.05    0.13
Q7    1   0.4466  0.3684  0.3643  11.00000  0.05    0.12
Q8    1   0.5774  0.2649  0.4226  11.00000  0.05    0.12
Q9    1   0.4821  0.4321  0.3427  11.00000  0.05    0.12
Q10   1   0.3385  0.7468  0.4021  11.00000  0.05    0.12
Q11   1   0.2227 -0.0318  0.2522  11.00000  0.05    0.11
Q12   1   0.9352  0.4728  0.3422  11.00000  0.05    0.11
Q13   1   0.1464  0.6148  0.1652  11.00000  0.05    0.11
Q14   1   0.2179  0.1567  0.2219  11.00000  0.05    0.11
Q15   1   0.6559  0.3861  0.3866  11.00000  0.05    0.11

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0447 for 1014 Fo > 4sig(Fo) and 0.0604 for all 14497 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.18, deepest hole -0.18
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0604
  REM R1_gt = 0.0447
  REM wR_ref = 0.1092
  REM GOOF = 1.071
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 14497
  REM Reflections_gt = 1014
  REM Parameters = n/a
  REM Hole = -0.18
  REM Peak = 0.18
  REM Flack = n/a

  
;
_olex2_submission_special_instructions 'No special instructions were received'
