# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_mo_mmv0105_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 1487390'
_audit_update_record             
;
2016-06-23 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;

_audit_creation_date             2016-06-17T13:43:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
'(Z)-1,1,1-trifluoro-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)-4-(pyrroli
;
_chemical_name_common            pyrazole
_chemical_formula_moiety         'C14 H15 F6 N3 O'
_chemical_formula_sum            'C14 H15 F6 N3 O'
_chemical_formula_weight         355.29
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   p21/n
_symmetry_space_group_name_Hall  '- p 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.790(7)
_cell_length_b                   7.792(4)
_cell_length_c                   16.696(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.74(2)
_cell_angle_gamma                90
_cell_volume                     1489.9(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9793
_cell_measurement_theta_min      2.412
_cell_measurement_theta_max      26.282

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_special_details           
;
'XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size'
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.9444
_exptl_absorpt_correction_T_max  0.978

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.1484
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_number            73762
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         26.86
_diffrn_reflns_theta_full        26.86
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             3176
_reflns_number_gt                2381
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-III'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         3176
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1381
_refine_ls_R_factor_gt           0.1162
_refine_ls_wR_factor_ref         0.3372
_refine_ls_wR_factor_gt          0.319
_refine_ls_goodness_of_fit_ref   1.421
_refine_ls_restrained_S_all      1.421
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.277
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.169

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
O O 0.0106 0.006 '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'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.1323(2) 0.4018(3) 0.62839(17) 0.0340(7) Uani 1 1 d . . .
F2 F 0.2107(2) 0.2670(3) 0.54256(15) 0.0257(7) Uani 1 1 d . . .
F6 F 0.8220(4) 0.1131(4) 0.4977(2) 0.0570(11) Uani 1 1 d . . .
F4 F 0.7376(2) 0.3410(3) 0.44447(16) 0.0307(7) Uani 1 1 d . . .
F5 F 0.8995(3) 0.3615(4) 0.53173(19) 0.0465(9) Uani 1 1 d . . .
F3 F 0.1448(3) 0.1273(3) 0.63329(17) 0.0370(8) Uani 1 1 d . . .
O1 O 0.7524(3) 0.1595(3) 0.63251(19) 0.0244(7) Uani 1 1 d . . .
N81 N 0.5748(3) 0.6471(4) 0.6488(2) 0.0162(8) Uani 1 1 d . . .
N2 N 0.4125(3) 0.3291(4) 0.6528(2) 0.0168(8) Uani 1 1 d . . .
C84 C 0.5067(4) 0.9264(5) 0.6053(3) 0.0216(9) Uani 1 1 d . . .
H84A H 0.5383 1.035 0.5922 0.026 Uiso 1 1 calc R . .
H84B H 0.4253 0.9187 0.5759 0.026 Uiso 1 1 calc R . .
C85 C 0.5771(4) 0.7751(5) 0.5840(3) 0.0193(9) Uani 1 1 d . . .
H85A H 0.5412 0.7297 0.5298 0.023 Uiso 1 1 calc R . .
H85B H 0.6565 0.8094 0.5852 0.023 Uiso 1 1 calc R . .
C8 C 0.6226(3) 0.4927(4) 0.6493(2) 0.0162(8) Uani 1 1 d . . .
C7 C 0.6169(3) 0.3754(4) 0.7205(2) 0.0152(8) Uani 1 1 d . . .
H7A H 0.6576 0.2693 0.7153 0.018 Uiso 1 1 calc R . .
H7B H 0.6563 0.4298 0.7718 0.018 Uiso 1 1 calc R . .
N1 N 0.4973(3) 0.3364(4) 0.7232(2) 0.0158(8) Uani 1 1 d . . .
C3 C 0.3183(4) 0.2832(5) 0.6794(2) 0.0167(8) Uani 1 1 d . . .
C6 C 0.2016(4) 0.2677(5) 0.6198(2) 0.0167(9) Uani 1 1 d . . .
C9 C 0.6808(3) 0.4429(5) 0.5895(2) 0.0178(9) Uani 1 1 d . . .
H9 H 0.6811 0.5207 0.5473 0.021 Uiso 1 1 calc R . .
C10 C 0.7395(3) 0.2852(5) 0.5867(3) 0.0190(9) Uani 1 1 d . . .
C11 C 0.8007(4) 0.2714(5) 0.5151(3) 0.0247(10) Uani 1 1 d . . .
C82 C 0.5144(4) 0.7151(5) 0.7103(3) 0.0198(9) Uani 1 1 d . . .
H82A H 0.5544 0.6821 0.7658 0.024 Uiso 1 1 calc R . .
H82B H 0.4341 0.6755 0.6993 0.024 Uiso 1 1 calc R . .
C83 C 0.5204(4) 0.9074(5) 0.6980(3) 0.0224(9) Uani 1 1 d . . .
H83A H 0.5947 0.9532 0.7284 0.027 Uiso 1 1 calc R . .
H83B H 0.4578 0.9657 0.7157 0.027 Uiso 1 1 calc R . .
C5 C 0.4587(4) 0.2980(5) 0.7920(2) 0.0184(9) Uani 1 1 d . . .
C4 C 0.3410(4) 0.2619(4) 0.7644(2) 0.0150(8) Uani 1 1 d . . .
H4 H 0.2888 0.2303 0.7956 0.018 Uiso 1 1 calc R . .
C15 C 0.5384(4) 0.2893(6) 0.8753(3) 0.0271(10) Uani 1 1 d . . .
H15A H 0.6154 0.3235 0.8721 0.041 Uiso 1 1 calc R . .
H15B H 0.5406 0.1739 0.8957 0.041 Uiso 1 1 calc R . .
H15C H 0.5107 0.3648 0.9119 0.041 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C6 1.355(5) . ?
F2 C6 1.320(5) . ?
F6 C11 1.305(5) . ?
F4 C11 1.350(5) . ?
F5 C11 1.332(5) . ?
F3 C6 1.329(4) . ?
O1 C10 1.230(5) . ?
N81 C8 1.328(5) . ?
N81 C85 1.477(5) . ?
N81 C82 1.479(5) . ?
N2 C3 1.339(5) . ?
N2 N1 1.351(5) . ?
C84 C83 1.526(6) . ?
C84 C85 1.531(5) . ?
C84 H84A 0.97 . ?
C84 H84B 0.97 . ?
C85 H85A 0.97 . ?
C85 H85B 0.97 . ?
C8 C9 1.394(6) . ?
C8 C7 1.514(5) . ?
C7 N1 1.453(5) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
N1 C5 1.366(5) . ?
C3 C4 1.390(6) . ?
C3 C6 1.498(6) . ?
C9 C10 1.416(5) . ?
C9 H9 0.93 . ?
C10 C11 1.539(6) . ?
C82 C83 1.516(5) . ?
C82 H82A 0.97 . ?
C82 H82B 0.97 . ?
C83 H83A 0.97 . ?
C83 H83B 0.97 . ?
C5 C4 1.383(6) . ?
C5 C15 1.483(6) . ?
C4 H4 0.93 . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?

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
C8 N81 C85 122.3(3) . . ?
C8 N81 C82 126.4(3) . . ?
C85 N81 C82 111.3(3) . . ?
C3 N2 N1 103.0(3) . . ?
C83 C84 C85 103.2(3) . . ?
C83 C84 H84A 111.1 . . ?
C85 C84 H84A 111.1 . . ?
C83 C84 H84B 111.1 . . ?
C85 C84 H84B 111.1 . . ?
H84A C84 H84B 109.1 . . ?
N81 C85 C84 104.2(3) . . ?
N81 C85 H85A 110.9 . . ?
C84 C85 H85A 110.9 . . ?
N81 C85 H85B 110.9 . . ?
C84 C85 H85B 110.9 . . ?
H85A C85 H85B 108.9 . . ?
N81 C8 C9 121.9(4) . . ?
N81 C8 C7 117.0(3) . . ?
C9 C8 C7 121.1(3) . . ?
N1 C7 C8 112.0(3) . . ?
N1 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N2 N1 C5 113.4(3) . . ?
N2 N1 C7 120.3(3) . . ?
C5 N1 C7 126.2(3) . . ?
N2 C3 C4 113.3(4) . . ?
N2 C3 C6 120.3(4) . . ?
C4 C3 C6 126.3(4) . . ?
F2 C6 F3 108.8(3) . . ?
F2 C6 F1 107.3(3) . . ?
F3 C6 F1 106.0(3) . . ?
F2 C6 C3 112.0(3) . . ?
F3 C6 C3 112.0(3) . . ?
F1 C6 C3 110.5(3) . . ?
C8 C9 C10 126.3(4) . . ?
C8 C9 H9 116.8 . . ?
C10 C9 H9 116.8 . . ?
O1 C10 C9 131.3(4) . . ?
O1 C10 C11 114.6(4) . . ?
C9 C10 C11 114.2(4) . . ?
F6 C11 F5 109.9(4) . . ?
F6 C11 F4 106.3(4) . . ?
F5 C11 F4 104.1(4) . . ?
F6 C11 C10 112.9(4) . . ?
F5 C11 C10 110.5(4) . . ?
F4 C11 C10 112.8(4) . . ?
N81 C82 C83 102.4(3) . . ?
N81 C82 H82A 111.3 . . ?
C83 C82 H82A 111.3 . . ?
N81 C82 H82B 111.3 . . ?
C83 C82 H82B 111.3 . . ?
H82A C82 H82B 109.2 . . ?
C82 C83 C84 103.6(3) . . ?
C82 C83 H83A 111 . . ?
C84 C83 H83A 111 . . ?
C82 C83 H83B 111 . . ?
C84 C83 H83B 111 . . ?
H83A C83 H83B 109 . . ?
N1 C5 C4 105.8(3) . . ?
N1 C5 C15 122.3(4) . . ?
C4 C5 C15 131.7(4) . . ?
C5 C4 C3 104.6(4) . . ?
C5 C4 H4 127.7 . . ?
C3 C4 H4 127.7 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N81 C85 C84 176.8(3) . . . . ?
C82 N81 C85 C84 -3.5(4) . . . . ?
C83 C84 C85 N81 25.9(4) . . . . ?
C85 N81 C8 C9 1.5(6) . . . . ?
C82 N81 C8 C9 -178.1(4) . . . . ?
C85 N81 C8 C7 178.5(3) . . . . ?
C82 N81 C8 C7 -1.1(6) . . . . ?
N81 C8 C7 N1 61.5(4) . . . . ?
C9 C8 C7 N1 -121.6(4) . . . . ?
C3 N2 N1 C5 -0.5(4) . . . . ?
C3 N2 N1 C7 177.2(3) . . . . ?
C8 C7 N1 N2 31.1(4) . . . . ?
C8 C7 N1 C5 -151.5(3) . . . . ?
N1 N2 C3 C4 0.2(4) . . . . ?
N1 N2 C3 C6 177.4(3) . . . . ?
N2 C3 C6 F2 13.6(5) . . . . ?
C4 C3 C6 F2 -169.6(3) . . . . ?
N2 C3 C6 F3 136.2(4) . . . . ?
C4 C3 C6 F3 -47.0(5) . . . . ?
N2 C3 C6 F1 -105.9(4) . . . . ?
C4 C3 C6 F1 70.9(5) . . . . ?
N81 C8 C9 C10 176.7(4) . . . . ?
C7 C8 C9 C10 -0.1(6) . . . . ?
C8 C9 C10 O1 0.8(7) . . . . ?
C8 C9 C10 C11 -177.1(4) . . . . ?
O1 C10 C11 F6 21.9(5) . . . . ?
C9 C10 C11 F6 -159.8(4) . . . . ?
O1 C10 C11 F5 -101.6(4) . . . . ?
C9 C10 C11 F5 76.6(5) . . . . ?
O1 C10 C11 F4 142.3(4) . . . . ?
C9 C10 C11 F4 -39.4(5) . . . . ?
C8 N81 C82 C83 159.3(4) . . . . ?
C85 N81 C82 C83 -20.3(4) . . . . ?
N81 C82 C83 C84 36.0(4) . . . . ?
C85 C84 C83 C82 -38.7(4) . . . . ?
N2 N1 C5 C4 0.6(4) . . . . ?
C7 N1 C5 C4 -177.0(3) . . . . ?
N2 N1 C5 C15 176.7(3) . . . . ?
C7 N1 C5 C15 -0.9(6) . . . . ?
N1 C5 C4 C3 -0.4(4) . . . . ?
C15 C5 C4 C3 -176.0(4) . . . . ?
N2 C3 C4 C5 0.1(4) . . . . ?
C6 C3 C4 C5 -176.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C84 H84A O1 0.97 2.64 3.357(5) 131.2 1_565
C82 H82A O1 0.97 2.5 3.348(6) 145.6 2_656

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

data_mo_mmv0080_01a
_database_code_depnum_ccdc_archive 'CCDC 1487398'
_audit_update_record             
;
2016-06-23 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;

_audit_creation_date             2016-06-21T14:03:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
'4-(diethylamino)-5-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)pent-3-en-2-on
;
_chemical_name_common            pyrazole
_chemical_formula_moiety         'C14 H17 F6 N3 O'
_chemical_formula_sum            'C14 H17 F6 N3 O'
_chemical_formula_weight         357.31
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.650(5)
_cell_length_b                   18.430(5)
_cell_length_c                   15.238(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     3272(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9898
_cell_measurement_theta_min      2.462
_cell_measurement_theta_max      28.2

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.501
_exptl_crystal_size_mid          0.481
_exptl_crystal_size_min          0.221
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.14
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_T_max  0.97

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.1619
_diffrn_reflns_av_unetI/netI     0.1039
_diffrn_reflns_number            9329
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_reflns_number_total             3772
_reflns_number_gt                2538
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER APEX-III'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1774P)²+6.3175P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         3772
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1432
_refine_ls_R_factor_gt           0.1065
_refine_ls_wR_factor_ref         0.3125
_refine_ls_wR_factor_gt          0.2811
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.802
_refine_diff_density_min         -1.009
_refine_diff_density_rms         0.128

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
O O 0.0106 0.006 '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'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F13 F 0.8504(2) 0.14158(15) 0.93054(13) 0.0297(7) Uani 1 1 d . . .
F14 F 0.68818(19) 0.11934(18) 0.87267(14) 0.0378(8) Uani 1 1 d . . .
C8 C 0.8111(3) 0.0899(2) 0.6235(2) 0.0158(8) Uani 1 1 d . . .
C5 C 0.9749(3) 0.2016(2) 0.5200(2) 0.0218(9) Uani 1 1 d . . .
O1 O 0.9519(2) 0.15234(17) 0.77674(16) 0.0247(7) Uani 1 1 d . . .
C81 C 0.7655(3) 0.0358(2) 0.4779(2) 0.0211(9) Uani 1 1 d . . .
H81A H 0.7174 -0.0064 0.4681 0.025 Uiso 1 1 calc R . .
H81B H 0.8447 0.0196 0.4799 0.025 Uiso 1 1 calc R . .
N8 N 0.7349(3) 0.06911(19) 0.56294(18) 0.0178(7) Uani 1 1 d . . .
C83 C 0.6104(3) 0.0704(2) 0.5806(2) 0.0231(9) Uani 1 1 d . . .
H83A H 0.5692 0.0753 0.5256 0.028 Uiso 1 1 calc R . .
H83B H 0.5923 0.1122 0.6167 0.028 Uiso 1 1 calc R . .
C84 C 0.5706(3) 0.0017(3) 0.6272(3) 0.0304(10) Uani 1 1 d . . .
H84A H 0.4895 0.0044 0.6377 0.046 Uiso 1 1 calc R . .
H84B H 0.6103 -0.0029 0.6821 0.046 Uiso 1 1 calc R . .
H84C H 0.587 -0.0397 0.5911 0.046 Uiso 1 1 calc R . .
N2 N 1.0235(2) 0.09460(19) 0.45795(18) 0.0192(7) Uani 1 1 d . . .
N1 N 0.9744(2) 0.12872(19) 0.52749(17) 0.0169(7) Uani 1 1 d . . .
C7 C 0.9380(3) 0.0847(2) 0.6026(2) 0.0166(8) Uani 1 1 d . . .
H7A H 0.9813 0.0997 0.6539 0.02 Uiso 1 1 calc R . .
H7B H 0.9569 0.0343 0.5909 0.02 Uiso 1 1 calc R . .
C4 C 1.0268(3) 0.2165(2) 0.4405(2) 0.0230(9) Uani 1 1 d . . .
H4 H 1.0408 0.2618 0.4158 0.028 Uiso 1 1 calc R . .
C3 C 1.0536(3) 0.1493(2) 0.4057(2) 0.0209(9) Uani 1 1 d . . .
F12 F 0.7588(3) 0.22673(17) 0.86629(17) 0.0448(8) Uani 1 1 d . . .
C82 C 0.7507(3) 0.0885(3) 0.4021(2) 0.0292(10) Uani 1 1 d . . .
H82A H 0.7708 0.0649 0.3481 0.044 Uiso 1 1 calc R . .
H82B H 0.7996 0.1298 0.4108 0.044 Uiso 1 1 calc R . .
H82C H 0.6722 0.1042 0.3994 0.044 Uiso 1 1 calc R . .
C6 C 1.1082(4) 0.1330(3) 0.3197(2) 0.0273(10) Uani 1 1 d . . .
C10 C 0.8483(3) 0.1388(2) 0.7746(2) 0.0193(8) Uani 1 1 d . . .
C9 C 0.7767(3) 0.1126(2) 0.7067(2) 0.0199(8) Uani 1 1 d . . .
H9 H 0.6985 0.1103 0.7189 0.024 Uiso 1 1 calc R . .
C11 C 0.7842(3) 0.1567(2) 0.8607(2) 0.0217(9) Uani 1 1 d . . .
F3 F 1.1712(5) 0.1842(3) 0.2912(3) 0.109(2) Uani 1 1 d . . .
F2 F 1.0323(4) 0.1272(4) 0.2564(2) 0.116(2) Uani 1 1 d . . .
F1 F 1.1605(6) 0.0738(3) 0.3168(3) 0.155(3) Uani 1 1 d . . .
C51 C 0.9294(4) 0.2513(3) 0.5895(2) 0.0301(10) Uani 1 1 d . . .
H51A H 0.8993 0.2231 0.6372 0.045 Uiso 1 1 calc R . .
H51B H 0.8695 0.2809 0.5653 0.045 Uiso 1 1 calc R . .
H51C H 0.9903 0.2817 0.6106 0.045 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
F13 C11 1.343(4) . ?
F14 C11 1.327(5) . ?
C8 N8 1.336(4) . ?
C8 C9 1.395(5) . ?
C8 C7 1.514(5) . ?
C5 N1 1.348(6) . ?
C5 C4 1.383(5) . ?
C5 C51 1.497(5) . ?
O1 C10 1.233(4) . ?
C81 N8 1.477(4) . ?
C81 C82 1.520(6) . ?
N8 C83 1.476(5) . ?
C83 C84 1.524(6) . ?
N2 C3 1.332(5) . ?
N2 N1 1.358(4) . ?
N1 C7 1.466(4) . ?
C4 C3 1.382(6) . ?
C3 C6 1.488(5) . ?
F12 C11 1.327(6) . ?
C6 F1 1.252(6) . ?
C6 F3 1.272(6) . ?
C6 F2 1.313(6) . ?
C10 C9 1.413(5) . ?
C10 C11 1.545(5) . ?

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
N8 C8 C9 121.5(3) . . ?
N8 C8 C7 119.0(3) . . ?
C9 C8 C7 119.4(3) . . ?
N1 C5 C4 105.9(3) . . ?
N1 C5 C51 123.3(3) . . ?
C4 C5 C51 130.8(4) . . ?
N8 C81 C82 112.0(4) . . ?
C8 N8 C83 121.5(3) . . ?
C8 N8 C81 124.4(3) . . ?
C83 N8 C81 113.8(3) . . ?
N8 C83 C84 111.7(3) . . ?
C3 N2 N1 103.1(3) . . ?
C5 N1 N2 113.2(3) . . ?
C5 N1 C7 128.2(3) . . ?
N2 N1 C7 118.3(3) . . ?
N1 C7 C8 114.3(3) . . ?
C3 C4 C5 104.8(4) . . ?
N2 C3 C4 113.0(3) . . ?
N2 C3 C6 119.1(4) . . ?
C4 C3 C6 127.9(4) . . ?
F1 C6 F3 110.8(5) . . ?
F1 C6 F2 103.3(6) . . ?
F3 C6 F2 101.4(5) . . ?
F1 C6 C3 114.6(4) . . ?
F3 C6 C3 113.4(4) . . ?
F2 C6 C3 112.1(4) . . ?
O1 C10 C9 131.8(3) . . ?
O1 C10 C11 114.0(3) . . ?
C9 C10 C11 114.2(3) . . ?
C8 C9 C10 126.7(3) . . ?
F14 C11 F12 107.9(3) . . ?
F14 C11 F13 105.5(3) . . ?
F12 C11 F13 106.2(3) . . ?
F14 C11 C10 114.4(3) . . ?
F12 C11 C10 111.7(3) . . ?
F13 C11 C10 110.6(3) . . ?

# END of CIF
