# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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. 
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data_sb747_hy_compound_7f
_database_code_depnum_ccdc_archive 'CCDC 1038684'
_audit_update_record             
;
2014-12-10 deposited with the CCDC.
2015-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 N-(7-trifluoromethyl)-1H-indazol-3-yl)butyramide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 F3 N3 O'
_chemical_formula_sum            'C12 H12 F3 N3 O'
_chemical_formula_weight         271.25

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8788(4)
_cell_length_b                   10.1605(6)
_cell_length_c                   12.1307(9)
_cell_angle_alpha                79.331(5)
_cell_angle_beta                 81.744(7)
_cell_angle_gamma                86.251(5)
_cell_volume                     584.35(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    44
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       rods
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.134
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8163
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
 dx = 35 mm, 180 sec./deg., 2 deg., 5 sets, 252 frames
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in φ and ω, 2°'
_diffrn_detector_area_resol_mean .
_diffrn_reflns_number            6971
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.897
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2681
_reflns_number_gt                2010
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       Collect
_computing_cell_refinement       EVALCCD
_computing_data_reduction        EVALCCD
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    Shelxtl-plus
_computing_publication_material  publCIF

_refine_special_details          
;
 CF3-group disordered, use of restraints (SADI, RIGU) for the refinement
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.1979P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2681
_refine_ls_number_parameters     206
_refine_ls_number_restraints     83
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.2819(3) 0.43391(14) 0.43968(12) 0.0174(3) Uani 1 1 d D . . . .
H1 H 0.200(3) 0.5108(15) 0.4126(15) 0.021 Uiso 1 1 d D U . . .
N2 N 0.1677(3) 0.36719(13) 0.54177(11) 0.0173(3) Uani 1 1 d . . . . .
C3 C 0.3219(3) 0.25630(15) 0.56369(13) 0.0156(3) Uani 1 1 d . . . . .
N31 N 0.2416(3) 0.16387(13) 0.66177(11) 0.0161(3) Uani 1 1 d D . . . .
H31 H 0.070(3) 0.1542(18) 0.6828(15) 0.019 Uiso 1 1 d D U . . .
C31 C 0.4166(3) 0.09602(15) 0.73152(13) 0.0156(3) Uani 1 1 d . . . . .
O31 O 0.6701(2) 0.10271(11) 0.71007(10) 0.0206(3) Uani 1 1 d . . . . .
C32 C 0.2792(3) 0.01223(16) 0.83788(14) 0.0187(3) Uani 1 1 d . . . . .
H32A H 0.0964 -0.0135 0.8242 0.022 Uiso 1 1 calc R U . . .
H32B H 0.2469 0.0669 0.8985 0.022 Uiso 1 1 calc R U . . .
C33 C 0.4486(3) -0.11418(16) 0.87834(14) 0.0205(3) Uani 1 1 d . . . . .
H33A H 0.4811 -0.1693 0.8180 0.025 Uiso 1 1 calc R U . . .
H33B H 0.6312 -0.0889 0.8926 0.025 Uiso 1 1 calc R U . . .
C34 C 0.3047(4) -0.19700(18) 0.98568(15) 0.0267(4) Uani 1 1 d . . . . .
H34A H 0.4205 -0.2771 1.0087 0.040 Uiso 1 1 calc R U . . .
H34B H 0.2755 -0.1435 1.0461 0.040 Uiso 1 1 calc R U . . .
H34C H 0.1254 -0.2239 0.9716 0.040 Uiso 1 1 calc R U . . .
C3A C 0.5440(3) 0.24778(15) 0.47471(13) 0.0155(3) Uani 1 1 d . . . . .
C4 C 0.7596(3) 0.15421(16) 0.45132(14) 0.0178(3) Uani 1 1 d . . . . .
H4 H 0.7814 0.0727 0.5027 0.021 Uiso 1 1 calc R U . . .
C5 C 0.9380(3) 0.18317(16) 0.35257(14) 0.0193(3) Uani 1 1 d . . . . .
H5 H 1.0853 0.1211 0.3357 0.023 Uiso 1 1 calc R U . . .
C6 C 0.9062(3) 0.30308(17) 0.27610(14) 0.0198(3) Uani 1 1 d . . . . .
H6 H 1.0356 0.3212 0.2093 0.024 Uiso 1 1 calc R U . . .
C7 C 0.6930(3) 0.39544(16) 0.29499(13) 0.0181(3) Uani 1 1 d D . . . .
C71 C 0.6561(3) 0.51637(18) 0.20813(14) 0.0260(4) Uani 1 1 d D U . . .
F71 F 0.486(2) 0.6108(9) 0.2471(9) 0.0299(15) Uani 0.54(3) 1 d D U P A 1
F72 F 0.8850(12) 0.5727(10) 0.1559(12) 0.058(2) Uani 0.54(3) 1 d D U P A 1
F73 F 0.523(2) 0.4812(7) 0.1264(7) 0.0391(15) Uani 0.54(3) 1 d D U P A 1
F71' F 0.452(2) 0.6000(10) 0.2404(10) 0.0309(19) Uani 0.46(3) 1 d D U P A 2
F72' F 0.8872(14) 0.5904(9) 0.1910(10) 0.0426(16) Uani 0.46(3) 1 d D U P A 2
F73' F 0.631(4) 0.4938(9) 0.1068(6) 0.051(2) Uani 0.46(3) 1 d D U P A 2
C7A C 0.5099(3) 0.36685(15) 0.39625(13) 0.0154(3) Uani 1 1 d . . . . .


_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 N2 1.3579(19) . ?
N1 C7A 1.358(2) . ?
N1 H1 0.883(14) . ?
N2 C3 1.3198(19) . ?
C3 N31 1.397(2) . ?
C3 C3A 1.426(2) . ?
N31 C31 1.354(2) . ?
N31 H31 0.846(14) . ?
C31 O31 1.2308(17) . ?
C31 C32 1.503(2) . ?
C32 C33 1.522(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.518(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C3A C4 1.405(2) . ?
C3A C7A 1.411(2) . ?
C4 C5 1.372(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(2) . ?
C6 H6 0.9500 . ?
C7 C7A 1.406(2) . ?
C7 C71 1.483(2) . ?
C71 F72 1.312(4) . ?
C71 F73' 1.315(5) . ?
C71 F71' 1.331(5) . ?
C71 F71 1.335(5) . ?
C71 F72' 1.366(5) . ?
C71 F73 1.371(4) . ?

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 C7A 111.80(12) . . ?
N2 N1 H1 117.3(12) . . ?
C7A N1 H1 130.9(12) . . ?
C3 N2 N1 106.28(12) . . ?
N2 C3 N31 118.56(13) . . ?
N2 C3 C3A 111.42(14) . . ?
N31 C3 C3A 129.89(14) . . ?
C31 N31 C3 124.96(12) . . ?
C31 N31 H31 116.9(12) . . ?
C3 N31 H31 118.0(12) . . ?
O31 C31 N31 122.65(14) . . ?
O31 C31 C32 122.10(14) . . ?
N31 C31 C32 115.25(13) . . ?
C31 C32 C33 113.30(13) . . ?
C31 C32 H32A 108.9 . . ?
C33 C32 H32A 108.9 . . ?
C31 C32 H32B 108.9 . . ?
C33 C32 H32B 108.9 . . ?
H32A C32 H32B 107.7 . . ?
C34 C33 C32 112.17(13) . . ?
C34 C33 H33A 109.2 . . ?
C32 C33 H33A 109.2 . . ?
C34 C33 H33B 109.2 . . ?
C32 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C4 C3A C7A 120.12(14) . . ?
C4 C3A C3 136.05(15) . . ?
C7A C3A C3 103.82(13) . . ?
C5 C4 C3A 118.53(15) . . ?
C5 C4 H4 120.7 . . ?
C3A C4 H4 120.7 . . ?
C4 C5 C6 121.00(14) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 121.99(15) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C7A 117.39(15) . . ?
C6 C7 C71 120.11(15) . . ?
C7A C7 C71 122.45(14) . . ?
F73' C71 F71' 109.6(6) . . ?
F72 C71 F71 108.2(6) . . ?
F73' C71 F72' 104.0(5) . . ?
F71' C71 F72' 104.0(6) . . ?
F72 C71 F73 106.7(4) . . ?
F71 C71 F73 103.5(5) . . ?
F72 C71 C7 115.7(4) . . ?
F73' C71 C7 115.6(4) . . ?
F71' C71 C7 113.4(5) . . ?
F71 C71 C7 113.4(5) . . ?
F72' C71 C7 109.1(4) . . ?
F73 C71 C7 108.4(3) . . ?
N1 C7A C7 132.36(14) . . ?
N1 C7A C3A 106.68(14) . . ?
C7 C7A C3A 120.95(14) . . ?

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
C7A N1 N2 C3 -0.41(17) . . . . ?
N1 N2 C3 N31 -176.39(13) . . . . ?
N1 N2 C3 C3A -0.13(16) . . . . ?
N2 C3 N31 C31 -139.00(15) . . . . ?
C3A C3 N31 C31 45.5(2) . . . . ?
C3 N31 C31 O31 -5.4(2) . . . . ?
C3 N31 C31 C32 174.21(14) . . . . ?
O31 C31 C32 C33 -32.8(2) . . . . ?
N31 C31 C32 C33 147.59(14) . . . . ?
C31 C32 C33 C34 -179.87(14) . . . . ?
N2 C3 C3A C4 -177.73(17) . . . . ?
N31 C3 C3A C4 -2.0(3) . . . . ?
N2 C3 C3A C7A 0.59(17) . . . . ?
N31 C3 C3A C7A 176.30(14) . . . . ?
C7A C3A C4 C5 1.6(2) . . . . ?
C3 C3A C4 C5 179.71(17) . . . . ?
C3A C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C7 -1.4(2) . . . . ?
C5 C6 C7 C7A 1.6(2) . . . . ?
C5 C6 C7 C71 -175.75(15) . . . . ?
C6 C7 C71 F72 -39.5(8) . . . . ?
C7A C7 C71 F72 143.3(8) . . . . ?
C6 C7 C71 F73' 55.6(10) . . . . ?
C7A C7 C71 F73' -121.7(10) . . . . ?
C6 C7 C71 F71' -176.5(7) . . . . ?
C7A C7 C71 F71' 6.2(8) . . . . ?
C6 C7 C71 F71 -165.4(6) . . . . ?
C7A C7 C71 F71 17.4(6) . . . . ?
C6 C7 C71 F72' -61.2(6) . . . . ?
C7A C7 C71 F72' 121.6(6) . . . . ?
C6 C7 C71 F73 80.3(5) . . . . ?
C7A C7 C71 F73 -97.0(5) . . . . ?
N2 N1 C7A C7 179.87(15) . . . . ?
N2 N1 C7A C3A 0.79(17) . . . . ?
C6 C7 C7A N1 -179.23(16) . . . . ?
C71 C7 C7A N1 -1.9(3) . . . . ?
C6 C7 C7A C3A -0.3(2) . . . . ?
C71 C7 C7A C3A 177.07(14) . . . . ?
C4 C3A C7A N1 177.85(13) . . . . ?
C3 C3A C7A N1 -0.80(16) . . . . ?
C4 C3A C7A C7 -1.4(2) . . . . ?
C3 C3A C7A C7 179.99(13) . . . . ?

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
N1 H1 N2 0.883(14) 2.177(16) 2.8972(18) 138.3(15) 2_566
N31 H31 O31 0.846(14) 2.018(14) 2.8505(16) 167.7(17) 1_455

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.050

_shelxl_version_number           2014-3

