# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_PRS-117-3
_database_code_depnum_ccdc_archive 'CCDC 1855401'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-09-18 downloaded from the CCDC.
;
_audit_creation_date             2018-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_systematic        
2''-bromo-4-methyl-5'-(piperidin-1-yl)-[1,1':3',1''-terphenyl]-4'-carbonitrile
_chemical_formula_moiety         '0.1(C25 H23 Br N2)'
_chemical_formula_sum            'C2.5 H2.3 Br0.1 N0.2'
_chemical_formula_weight         43.14
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.4375(6)
_cell_length_b                   19.2059(12)
_cell_length_c                   13.8112(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.900(7)
_cell_angle_gamma                90
_cell_volume                     2152.5(3)
_cell_formula_units_Z            40
_cell_measurement_reflns_used    4452
_cell_measurement_temperature    298
_cell_measurement_theta_max      20.9940
_cell_measurement_theta_min      3.2640
_exptl_absorpt_coefficient_mu    1.922
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.3311
_exptl_crystal_description       needle
_exptl_crystal_F_000             887.1716
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane and DCM'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30605
_diffrn_reflns_theta_full        24.9996
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.25
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 15.9853
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -13.00   18.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0952  -99.0000    0.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega  -46.00   52.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.0952   77.0000 -150.0000 98

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00   62.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3140  -99.0000  120.0000 87

#__ type_ start__ end____ width___ exp.time_
  4 omega  -22.00   62.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3140  -99.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega    2.00   62.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3140   57.0000 -150.0000 60

#__ type_ start__ end____ width___ exp.time_
  6 omega    6.00   89.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3140   57.0000    0.0000 83

#__ type_ start__ end____ width___ exp.time_
  7 omega    1.00   89.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3140   57.0000  120.0000 88

#__ type_ start__ end____ width___ exp.time_
  8 omega   16.00   89.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3140   57.0000  -90.0000 73

#__ type_ start__ end____ width___ exp.time_
  9 omega  -35.00   42.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       20.3140  -38.0000  -30.0000 77
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -10
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              -6
_reflns_number_gt                2795
_reflns_number_total             3776
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.5261
_refine_diff_density_min         -0.7467
_refine_diff_density_rms         0.0987
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             6.2767
_refine_ls_goodness_of_fit_ref   1.0390
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    39
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3776
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.0390
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1679
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C19(H19a,H19b), C20(H20a,H20b), C21(H21a,H21b), C22(H22a,H22b)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C10(H10), C16(H16), C18(H18), C23(H23), C25(H25),
 C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C26(H26a,H26b,H26c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Br1 Br 0.81742(6) 0.03240(3) 0.76240(4) 0.0806(3) Uani 1.000000 .
N1 N 1.3389(4) -0.08372(15) 0.6286(2) 0.0469(8) Uani 1.000000 .
C2 C 1.2793(4) -0.01865(18) 0.6439(3) 0.0412(9) Uani 1.000000 .
C3 C 1.1359(4) 0.14869(19) 0.4996(3) 0.0433(9) Uani 1.000000 .
C4 C 1.1546(4) 0.21911(19) 0.5205(3) 0.0458(9) Uani 1.000000 .
H4 H 1.1863(4) 0.23408(19) 0.5870(3) 0.0549(11) Uiso 1.000000 R
C5 C 1.2392(5) 0.03178(17) 0.5683(3) 0.0442(9) Uani 1.000000 .
H5 H 1.2582(5) 0.02222(17) 0.5065(3) 0.0531(11) Uiso 1.000000 R
C6 C 1.1717(4) 0.09584(18) 0.5823(3) 0.0420(8) Uani 1.000000 .
C7 C 1.1801(4) 0.0621(2) 0.7516(2) 0.0411(8) Uani 1.000000 .
C8 C 1.1422(4) 0.11022(19) 0.6748(3) 0.0439(9) Uani 1.000000 .
H8 H 1.0965(4) 0.15279(19) 0.6847(3) 0.0527(10) Uiso 1.000000 R
N9 N 1.2828(5) -0.0951(2) 0.8757(3) 0.0737(11) Uani 1.000000 .
C10 C 1.0825(4) 0.1281(2) 0.3993(3) 0.0487(9) Uani 1.000000 .
H10 H 1.0667(4) 0.0811(2) 0.3832(3) 0.0584(11) Uiso 1.000000 R
C11 C 1.2476(5) -0.00264(19) 0.7371(3) 0.0416(8) Uani 1.000000 .
C12 C 1.1467(5) 0.07788(18) 0.8505(3) 0.0451(9) Uani 1.000000 .
C13 C 0.9932(5) 0.06887(19) 0.8662(3) 0.0524(10) Uani 1.000000 .
C14 C 1.0774(4) 0.2476(2) 0.3440(3) 0.0518(10) Uani 1.000000 .
C15 C 1.2699(5) -0.0543(2) 0.8145(3) 0.0500(9) Uani 1.000000 .
C16 C 1.1266(4) 0.2676(2) 0.4434(3) 0.0527(10) Uani 1.000000 .
H16 H 1.1414(4) 0.3147(2) 0.4592(3) 0.0633(12) Uiso 1.000000 R
C17 C 1.3155(5) -0.1882(2) 0.5279(3) 0.0638(12) Uani 1.000000 .
H17a H 1.2218(5) -0.2050(2) 0.5491(3) 0.0765(14) Uiso 1.000000 R
H17b H 1.3048(5) -0.2055(2) 0.4605(3) 0.0765(14) Uiso 1.000000 R
C18 C 1.0529(4) 0.1777(2) 0.3231(3) 0.0541(10) Uani 1.000000 .
H18 H 1.0157(4) 0.1633(2) 0.2565(3) 0.0650(12) Uiso 1.000000 R
C19 C 1.4959(5) -0.1070(2) 0.6953(3) 0.0578(11) Uani 1.000000 .
H19a H 1.5855(5) -0.0907(2) 0.6697(3) 0.0693(13) Uiso 1.000000 R
H19b H 1.5103(5) -0.0873(2) 0.7618(3) 0.0693(13) Uiso 1.000000 R
C20 C 1.3131(5) -0.1099(2) 0.5260(3) 0.0558(10) Uani 1.000000 .
H20a H 1.2080(5) -0.0935(2) 0.4839(3) 0.0670(12) Uiso 1.000000 R
H20b H 1.3993(5) -0.0927(2) 0.4981(3) 0.0670(12) Uiso 1.000000 R
C21 C 1.4721(5) -0.2166(2) 0.5982(4) 0.0744(13) Uani 1.000000 .
H21a H 1.4641(5) -0.2668(2) 0.6025(4) 0.0893(16) Uiso 1.000000 R
H21b H 1.5646(5) -0.2059(2) 0.5718(4) 0.0893(16) Uiso 1.000000 R
C22 C 1.5015(6) -0.1852(2) 0.7024(4) 0.0681(12) Uani 1.000000 .
H22a H 1.6082(6) -0.1999(2) 0.7445(4) 0.0817(15) Uiso 1.000000 R
H22b H 1.4177(6) -0.2015(2) 0.7331(4) 0.0817(15) Uiso 1.000000 R
C23 C 0.9661(6) 0.0846(2) 0.9588(3) 0.0671(13) Uani 1.000000 .
H23 H 0.8624(6) 0.0781(2) 0.9687(3) 0.0805(16) Uiso 1.000000 R
C25 C 1.2745(6) 0.1025(2) 0.9302(3) 0.0679(12) Uani 1.000000 .
H25 H 1.3796(6) 0.1078(2) 0.9220(3) 0.0814(15) Uiso 1.000000 R
C26 C 1.0545(6) 0.3008(3) 0.2598(4) 0.0814(14) Uani 1.000000 .
H26a H 0.981(3) 0.3368(10) 0.2691(15) 0.122(2) Uiso 1.000000 GR
H26b H 1.1592(9) 0.3208(13) 0.2610(17) 0.122(2) Uiso 1.000000 GR
H26c H 1.009(4) 0.2783(4) 0.1962(4) 0.122(2) Uiso 1.000000 GR
C27 C 1.0924(9) 0.1096(3) 1.0349(3) 0.0819(16) Uani 1.000000 .
H27 H 1.0742(9) 0.1203(3) 1.0967(3) 0.0983(19) Uiso 1.000000 R
C28 C 1.2455(8) 0.1190(3) 1.0215(3) 0.0840(15) Uani 1.000000 .
H28 H 1.3304(8) 0.1365(3) 1.0738(3) 0.1009(18) Uiso 1.000000 R


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
Br1 C13 1.892(4) . ?
N1 C2 1.385(4) . ?
N1 C19 1.461(5) . ?
N1 C20 1.462(4) . ?
C2 C5 1.396(5) . ?
C2 C11 1.418(5) . ?
C3 C4 1.383(5) . ?
C3 C6 1.496(5) . ?
C3 C10 1.391(5) . ?
C4 C16 1.385(5) . ?
C5 C6 1.391(5) . ?
C6 C8 1.394(5) . ?
C7 C8 1.376(5) . ?
C7 C11 1.405(6) . ?
C7 C12 1.499(4) . ?
N9 C15 1.134(5) . ?
C10 C18 1.390(5) . ?
C11 C15 1.433(6) . ?
C12 C13 1.382(5) . ?
C12 C25 1.395(5) . ?
C13 C23 1.393(5) . ?
C14 C16 1.376(5) . ?
C14 C18 1.377(6) . ?
C14 C26 1.519(6) . ?
C17 C20 1.505(6) . ?
C17 C21 1.511(6) . ?
C19 C22 1.504(6) . ?
C21 C22 1.517(6) . ?
C23 C27 1.363(7) . ?
C25 C28 1.385(6) . ?
C27 C28 1.366(8) . ?

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
C19 N1 C2 119.0(3) . . ?
C20 N1 C2 119.6(3) . . ?
C20 N1 C19 112.0(3) . . ?
C5 C2 N1 122.4(3) . . ?
C11 C2 N1 120.0(3) . . ?
C11 C2 C5 117.4(3) . . ?
C6 C3 C4 121.1(3) . . ?
C10 C3 C4 118.2(3) . . ?
C10 C3 C6 120.7(3) . . ?
C16 C4 C3 120.8(3) . . ?
C6 C5 C2 122.3(3) . . ?
C5 C6 C3 119.9(3) . . ?
C8 C6 C3 121.1(3) . . ?
C8 C6 C5 119.0(3) . . ?
C11 C7 C8 120.1(3) . . ?
C12 C7 C8 120.3(3) . . ?
C12 C7 C11 119.5(3) . . ?
C7 C8 C6 120.8(3) . . ?
C18 C10 C3 120.1(4) . . ?
C7 C11 C2 120.4(3) . . ?
C15 C11 C2 120.6(3) . . ?
C15 C11 C7 118.8(3) . . ?
C13 C12 C7 122.4(3) . . ?
C25 C12 C7 119.4(3) . . ?
C25 C12 C13 118.2(3) . . ?
C12 C13 Br1 120.1(3) . . ?
C23 C13 Br1 119.0(3) . . ?
C23 C13 C12 120.9(4) . . ?
C18 C14 C16 117.9(4) . . ?
C26 C14 C16 121.1(4) . . ?
C26 C14 C18 121.0(4) . . ?
C11 C15 N9 178.0(4) . . ?
C14 C16 C4 121.4(4) . . ?
C21 C17 C20 112.1(4) . . ?
C14 C18 C10 121.6(4) . . ?
C22 C19 N1 110.7(3) . . ?
C17 C20 N1 109.2(3) . . ?
C22 C21 C17 110.7(3) . . ?
C21 C22 C19 109.9(4) . . ?
C27 C23 C13 119.6(4) . . ?
C28 C25 C12 120.3(4) . . ?
C28 C27 C23 120.7(4) . . ?
C27 C28 C25 120.2(5) . . ?

_olex2_submission_original_sample_id PRS-117
_olex2_submission_special_instructions 'No special instructions were received'
