# 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 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1583532'
_audit_update_record             
;
2018-04-18 deposited with the CCDC.
2018-05-10 downloaded from the CCDC.
;

_audit_creation_date             2018-04-17T12:30:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
        '6-(pyrrolidin-1-yl)-2-(p-tolyl)-4-(trifluoromethyl)quinoline'
;
_chemical_name_common            6-(pyrrolidin-1-yl)toluyl-quinoline
_chemical_formula_moiety         'C12 H19 F3 N2'
_chemical_formula_sum            'C21 H19 F3 N2'
_chemical_formula_weight         356.38
_chemical_melting_point          none
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
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'

_cell_length_a                   7.597(5)
_cell_length_b                   10.743(5)
_cell_length_c                   20.703(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1689.7(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9859
_cell_measurement_theta_min      2.7315
_cell_measurement_theta_max      26.672
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.055
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744

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

_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.7241
_exptl_absorpt_correction_T_max  0.7455
_exptl_transmission_factor_max   none
_exptl_transmission_factor_min   none
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.994

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

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.019
_diffrn_reflns_number            57067
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.733
_diffrn_reflns_theta_max         27.149
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_coverage         0.736
_reflns_number_total             3738
_reflns_number_gt                3385
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'BRUKER APEX-III'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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 > 2sigma(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     
'w=1/[σ²(Fo²)+(0.0467P)²+0.5543P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3738
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.085
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1344 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(15)
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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'
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_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
F43 F -0.34221(18) 1.28060(13) 0.92593(7) 0.0275(3) Uani 1 1 d . . . . .
F42 F -0.46554(19) 1.15960(14) 0.99567(6) 0.0258(3) Uani 1 1 d . . . . .
F44 F -0.62145(19) 1.29191(13) 0.94309(7) 0.0271(3) Uani 1 1 d . . . . .
N1 N -0.5916(2) 0.93975(17) 0.78989(8) 0.0157(4) Uani 1 1 d . . . . .
N61 N 0.0321(2) 0.89137(17) 0.92825(9) 0.0179(4) Uani 1 1 d . . . . .
C21 C -0.8669(3) 1.0368(2) 0.76185(10) 0.0155(4) Uani 1 1 d . . . . .
C6 C -0.1225(3) 0.9065(2) 0.89568(10) 0.0154(4) Uani 1 1 d . . . . .
C5 C -0.2359(3) 1.0049(2) 0.90910(10) 0.0152(4) Uani 1 1 d . . . . .
H5 H -0.206552 1.061845 0.941151 0.018 Uiso 1 1 calc R U . . .
C2 C -0.7029(3) 1.0321(2) 0.80098(10) 0.0156(4) Uani 1 1 d . . . . .
C3 C -0.6682(3) 1.1237(2) 0.84872(10) 0.0163(4) Uani 1 1 d . . . . .
H3 H -0.747616 1.188328 0.855292 0.02 Uiso 1 1 calc R U . . .
C65 C 0.1522(3) 0.7872(2) 0.91797(11) 0.0181(4) Uani 1 1 d . . . . .
H65A H 0.192025 0.784244 0.873483 0.022 Uiso 1 1 calc R U . . .
H65B H 0.096129 0.708746 0.928678 0.022 Uiso 1 1 calc R U . . .
C26 C -1.0087(3) 1.1128(2) 0.77879(11) 0.0182(5) Uani 1 1 d . . . . .
H26 H -0.999771 1.163607 0.815008 0.022 Uiso 1 1 calc R U . . .
C4A C -0.3946(3) 1.01914(19) 0.87470(10) 0.0140(4) Uani 1 1 d . . . . .
C62 C 0.0847(3) 0.9704(2) 0.98216(11) 0.0178(4) Uani 1 1 d . . . . .
H62A H -0.01442 0.987453 1.010345 0.021 Uiso 1 1 calc R U . . .
H62B H 0.132735 1.048694 0.966849 0.021 Uiso 1 1 calc R U . . .
C8A C -0.4408(3) 0.9332(2) 0.82525(10) 0.0154(4) Uani 1 1 d . . . . .
C7 C -0.1697(3) 0.8203(2) 0.84602(11) 0.0175(5) Uani 1 1 d . . . . .
H7 H -0.095064 0.754125 0.836527 0.021 Uiso 1 1 calc R U . . .
C8 C -0.3226(3) 0.8339(2) 0.81244(10) 0.0171(5) Uani 1 1 d . . . . .
H8 H -0.350318 0.77665 0.780309 0.021 Uiso 1 1 calc R U . . .
C24 C -1.1810(3) 1.0380(2) 0.68882(11) 0.0197(5) Uani 1 1 d . . . . .
C25 C -1.1618(3) 1.1140(2) 0.74284(11) 0.0190(5) Uani 1 1 d . . . . .
H25 H -1.253535 1.16641 0.754908 0.023 Uiso 1 1 calc R U . . .
C41 C -0.4871(3) 1.2114(2) 0.93692(11) 0.0187(5) Uani 1 1 d . . . . .
C22 C -0.8842(3) 0.9628(2) 0.70643(11) 0.0197(5) Uani 1 1 d . . . . .
H22 H -0.791526 0.912049 0.693476 0.024 Uiso 1 1 calc R U . . .
C4 C -0.5182(3) 1.11696(19) 0.88506(10) 0.0153(4) Uani 1 1 d . . . . .
C23 C -1.0384(3) 0.9648(2) 0.67089(11) 0.0215(5) Uani 1 1 d . . . . .
H23 H -1.046776 0.915823 0.633985 0.026 Uiso 1 1 calc R U . . .
C27 C -1.3521(3) 1.0357(2) 0.65179(12) 0.0253(5) Uani 1 1 d . . . . .
H27A H -1.434103 1.092159 0.671439 0.038 Uiso 1 1 calc R U . . .
H27B H -1.331154 1.060458 0.607908 0.038 Uiso 1 1 calc R U . . .
H27C H -1.399869 0.952969 0.652483 0.038 Uiso 1 1 calc R U . . .
C64 C 0.3054(3) 0.8144(2) 0.96384(12) 0.0217(5) Uani 1 1 d . . . . .
H64A H 0.353159 0.737918 0.981466 0.026 Uiso 1 1 calc R U . . .
H64B H 0.398483 0.859113 0.941701 0.026 Uiso 1 1 calc R U . . .
C63 C 0.2245(3) 0.8944(2) 1.01703(12) 0.0236(5) Uani 1 1 d . . . . .
H63A H 0.172212 0.842881 1.050389 0.028 Uiso 1 1 calc R U . . .
H63B H 0.312359 0.948088 1.036498 0.028 Uiso 1 1 calc R U . . .



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

_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
F43 C41 1.347(3) . ?
F42 C41 1.348(3) . ?
F44 C41 1.344(3) . ?
N1 C2 1.323(3) . ?
N1 C8A 1.361(3) . ?
N61 C6 1.364(3) . ?
N61 C62 1.458(3) . ?
N61 C65 1.459(3) . ?
C21 C26 1.396(3) . ?
C21 C22 1.402(3) . ?
C21 C2 1.487(3) . ?
C6 C5 1.392(3) . ?
C6 C7 1.429(3) . ?
C5 C4A 1.409(3) . ?
C2 C3 1.420(3) . ?
C3 C4 1.368(3) . ?
C65 C64 1.530(3) . ?
C26 C25 1.381(3) . ?
C4A C8A 1.423(3) . ?
C4A C4 1.425(3) . ?
C62 C63 1.522(3) . ?
C8A C8 1.419(3) . ?
C7 C8 1.362(3) . ?
C24 C23 1.389(4) . ?
C24 C25 1.392(3) . ?
C24 C27 1.509(3) . ?
C41 C4 1.496(3) . ?
C22 C23 1.383(3) . ?
C64 C63 1.526(3) . ?

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
C2 N1 C8A 118.90(19) . . ?
C6 N61 C62 123.02(18) . . ?
C6 N61 C65 123.87(19) . . ?
C62 N61 C65 112.77(18) . . ?
C26 C21 C22 117.7(2) . . ?
C26 C21 C2 121.96(19) . . ?
C22 C21 C2 120.3(2) . . ?
N61 C6 C5 121.6(2) . . ?
N61 C6 C7 119.6(2) . . ?
C5 C6 C7 118.7(2) . . ?
C6 C5 C4A 120.8(2) . . ?
N1 C2 C3 121.5(2) . . ?
N1 C2 C21 117.80(19) . . ?
C3 C2 C21 120.74(19) . . ?
C4 C3 C2 120.1(2) . . ?
N61 C65 C64 103.78(18) . . ?
C25 C26 C21 121.3(2) . . ?
C5 C4A C8A 120.28(19) . . ?
C5 C4A C4 124.61(19) . . ?
C8A C4A C4 115.11(19) . . ?
N61 C62 C63 103.97(18) . . ?
N1 C8A C8 118.1(2) . . ?
N1 C8A C4A 124.1(2) . . ?
C8 C8A C4A 117.8(2) . . ?
C8 C7 C6 120.8(2) . . ?
C7 C8 C8A 121.7(2) . . ?
C23 C24 C25 117.7(2) . . ?
C23 C24 C27 121.8(2) . . ?
C25 C24 C27 120.5(2) . . ?
C26 C25 C24 121.0(2) . . ?
F44 C41 F43 106.35(18) . . ?
F44 C41 F42 105.79(17) . . ?
F43 C41 F42 106.33(18) . . ?
F44 C41 C4 112.61(19) . . ?
F43 C41 C4 112.47(18) . . ?
F42 C41 C4 112.75(18) . . ?
C23 C22 C21 120.4(2) . . ?
C3 C4 C4A 120.33(19) . . ?
C3 C4 C41 119.39(19) . . ?
C4A C4 C41 120.3(2) . . ?
C22 C23 C24 121.8(2) . . ?
C63 C64 C65 104.45(18) . . ?
C62 C63 C64 103.93(19) . . ?



# END of CIF
