# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1520565'
_audit_update_record             
;
2016-12-03 deposited with the CCDC.
2018-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
4'-Bromo-3-piperidin-1-yl-biphenyl-4-carbonitrile
_chemical_name_common            biphenyl
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 Br N2'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      298(2)
_chemical_formula_weight         341.24

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.541(3)
_cell_length_b                   14.222(4)
_cell_length_c                   12.432(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.54(3)
_cell_angle_gamma                90
_cell_volume                     1579.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    292
_cell_measurement_theta_min      3.0039
_cell_measurement_theta_max      29.8553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.597
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.42917
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 15.9853
_diffrn_reflns_number            17476
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_av_R_equivalents  0.1071
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.326
_diffrn_reflns_theta_max         29.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3887
_reflns_number_gt                2064
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2014/7 (Sheldrick, 2014)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0844P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3887
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.1983
_refine_ls_wR_factor_gt          0.1571
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Br1 Br 0.92523(6) 0.19722(4) 1.08607(4) 0.0768(3) Uani 1 1 d . . . . .
N2 N 0.5795(4) 0.0647(2) 0.3062(3) 0.0464(8) Uani 1 1 d . . . . .
N1 N 0.6647(5) -0.1565(3) 0.2063(4) 0.0772(12) Uani 1 1 d . . . . .
C11 C 0.6790(4) 0.0231(3) 0.4053(3) 0.0438(9) Uani 1 1 d . . . . .
C4 C 0.8374(5) 0.0577(3) 0.7275(4) 0.0469(10) Uani 1 1 d . . . . .
C10 C 0.7473(5) -0.0630(3) 0.3963(4) 0.0506(10) Uani 1 1 d . . . . .
C12 C 0.7104(5) 0.0586(3) 0.5149(3) 0.0476(10) Uani 1 1 d . . . . .
H12 H 0.6624 0.1134 0.5239 0.057 Uiso 1 1 calc R U . . .
C5 C 0.7215(5) 0.0961(3) 0.7567(4) 0.0529(10) Uani 1 1 d . . . . .
H5 H 0.6247 0.0942 0.7032 0.063 Uiso 1 1 calc R U . . .
C18 C 0.4817(5) 0.1382(3) 0.3233(4) 0.0567(11) Uani 1 1 d . . . . .
H18A H 0.5401 0.1943 0.3535 0.068 Uiso 1 1 calc R U . . .
H18B H 0.4382 0.1171 0.3788 0.068 Uiso 1 1 calc R U . . .
C8 C 0.8828(5) -0.0654(3) 0.6007(4) 0.0568(11) Uani 1 1 d . . . . .
H8 H 0.9527 -0.0936 0.6647 0.068 Uiso 1 1 calc R U . . .
C1 C 0.8881(5) 0.1385(3) 0.9417(3) 0.0519(10) Uani 1 1 d . . . . .
C9 C 0.8504(5) -0.1046(3) 0.4930(4) 0.0576(11) Uani 1 1 d . . . . .
H9 H 0.8983 -0.1597 0.4850 0.069 Uiso 1 1 calc R U . . .
C6 C 0.7449(5) 0.1367(3) 0.8617(4) 0.0548(11) Uani 1 1 d . . . . .
H6 H 0.6655 0.1625 0.8786 0.066 Uiso 1 1 calc R U . . .
C2 C 1.0062(5) 0.0996(3) 0.9178(4) 0.0571(11) Uani 1 1 d . . . . .
H2 H 1.1021 0.1001 0.9726 0.068 Uiso 1 1 calc R U . . .
C7 C 0.8107(4) 0.0157(3) 0.6126(3) 0.0465(10) Uani 1 1 d . . . . .
C3 C 0.9799(5) 0.0596(3) 0.8110(4) 0.0556(11) Uani 1 1 d . . . . .
H3 H 1.0594 0.0334 0.7946 0.067 Uiso 1 1 calc R U . . .
C13 C 0.7030(5) -0.1138(3) 0.2894(4) 0.0577(11) Uani 1 1 d . . . . .
C15 C 0.5242(6) 0.1160(4) 0.1061(4) 0.0720(14) Uani 1 1 d . . . . .
H15A H 0.4680 0.0593 0.0754 0.086 Uiso 1 1 calc R U . . .
H15B H 0.5703 0.1374 0.0522 0.086 Uiso 1 1 calc R U . . .
C14 C 0.6441(5) 0.0947(3) 0.2201(4) 0.0606(12) Uani 1 1 d . . . . .
H14A H 0.7085 0.0453 0.2101 0.073 Uiso 1 1 calc R U . . .
H14B H 0.7050 0.1503 0.2477 0.073 Uiso 1 1 calc R U . . .
C16 C 0.4190(6) 0.1913(3) 0.1201(5) 0.0677(14) Uani 1 1 d . . . . .
H16A H 0.4724 0.2503 0.1421 0.081 Uiso 1 1 calc R U . . .
H16B H 0.3375 0.2008 0.0477 0.081 Uiso 1 1 calc R U . . .
C17 C 0.3577(5) 0.1613(3) 0.2105(4) 0.0610(12) Uani 1 1 d . . . . .
H17A H 0.2948 0.1064 0.1838 0.073 Uiso 1 1 calc R U . . .
H17B H 0.2960 0.2114 0.2230 0.073 Uiso 1 1 calc R U . . .


_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
Br1 C1 1.897(4) . ?
N2 C11 1.396(5) . ?
N2 C18 1.465(5) . ?
N2 C14 1.472(5) . ?
N1 C13 1.143(6) . ?
C11 C12 1.384(5) . ?
C11 C10 1.410(5) . ?
C4 C5 1.391(6) . ?
C4 C3 1.391(6) . ?
C4 C7 1.485(6) . ?
C10 C9 1.390(6) . ?
C10 C13 1.439(6) . ?
C12 C7 1.395(6) . ?
C12 H12 0.9300 . ?
C5 C6 1.372(6) . ?
C5 H5 0.9300 . ?
C18 C17 1.520(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C8 C7 1.378(6) . ?
C8 C9 1.382(6) . ?
C8 H8 0.9300 . ?
C1 C2 1.378(6) . ?
C1 C6 1.380(6) . ?
C9 H9 0.9300 . ?
C6 H6 0.9300 . ?
C2 C3 1.384(6) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C15 C14 1.507(6) . ?
C15 C16 1.519(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 C17 1.499(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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
C11 N2 C18 116.4(3) . . ?
C11 N2 C14 115.8(3) . . ?
C18 N2 C14 110.5(3) . . ?
C12 C11 N2 124.0(4) . . ?
C12 C11 C10 116.6(4) . . ?
N2 C11 C10 119.2(3) . . ?
C5 C4 C3 117.2(4) . . ?
C5 C4 C7 121.7(4) . . ?
C3 C4 C7 121.2(4) . . ?
C9 C10 C11 120.5(4) . . ?
C9 C10 C13 118.4(4) . . ?
C11 C10 C13 121.0(4) . . ?
C11 C12 C7 122.9(4) . . ?
C11 C12 H12 118.5 . . ?
C7 C12 H12 118.5 . . ?
C6 C5 C4 122.3(4) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
N2 C18 C17 110.4(3) . . ?
N2 C18 H18A 109.6 . . ?
C17 C18 H18A 109.6 . . ?
N2 C18 H18B 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C7 C8 C9 119.4(4) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C2 C1 C6 121.0(4) . . ?
C2 C1 Br1 119.0(3) . . ?
C6 C1 Br1 119.9(3) . . ?
C8 C9 C10 121.1(4) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C5 C6 C1 118.9(4) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
C1 C2 C3 119.0(4) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C8 C7 C12 119.2(4) . . ?
C8 C7 C4 121.1(4) . . ?
C12 C7 C4 119.7(4) . . ?
C2 C3 C4 121.6(4) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
N1 C13 C10 177.3(5) . . ?
C14 C15 C16 110.4(4) . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N2 C14 C15 111.6(4) . . ?
N2 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
N2 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C17 C16 C15 109.4(4) . . ?
C17 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C16 C17 C18 111.8(4) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?

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
C18 N2 C11 C12 -12.9(6) . . . . ?
C14 N2 C11 C12 119.4(4) . . . . ?
C18 N2 C11 C10 163.5(4) . . . . ?
C14 N2 C11 C10 -64.2(5) . . . . ?
C12 C11 C10 C9 -5.3(6) . . . . ?
N2 C11 C10 C9 178.0(4) . . . . ?
C12 C11 C10 C13 169.3(4) . . . . ?
N2 C11 C10 C13 -7.3(6) . . . . ?
N2 C11 C12 C7 -179.8(4) . . . . ?
C10 C11 C12 C7 3.7(6) . . . . ?
C3 C4 C5 C6 1.7(6) . . . . ?
C7 C4 C5 C6 -178.7(4) . . . . ?
C11 N2 C18 C17 -167.4(4) . . . . ?
C14 N2 C18 C17 57.9(5) . . . . ?
C7 C8 C9 C10 0.6(7) . . . . ?
C11 C10 C9 C8 3.3(7) . . . . ?
C13 C10 C9 C8 -171.5(4) . . . . ?
C4 C5 C6 C1 -0.8(6) . . . . ?
C2 C1 C6 C5 -0.7(6) . . . . ?
Br1 C1 C6 C5 178.2(3) . . . . ?
C6 C1 C2 C3 1.1(7) . . . . ?
Br1 C1 C2 C3 -177.8(3) . . . . ?
C9 C8 C7 C12 -2.3(6) . . . . ?
C9 C8 C7 C4 177.2(4) . . . . ?
C11 C12 C7 C8 0.1(6) . . . . ?
C11 C12 C7 C4 -179.5(4) . . . . ?
C5 C4 C7 C8 -140.0(4) . . . . ?
C3 C4 C7 C8 39.5(6) . . . . ?
C5 C4 C7 C12 39.6(6) . . . . ?
C3 C4 C7 C12 -140.9(4) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C5 C4 C3 C2 -1.2(6) . . . . ?
C7 C4 C3 C2 179.2(4) . . . . ?
C11 N2 C14 C15 165.9(4) . . . . ?
C18 N2 C14 C15 -59.1(5) . . . . ?
C16 C15 C14 N2 57.4(5) . . . . ?
C14 C15 C16 C17 -54.6(6) . . . . ?
C15 C16 C17 C18 55.0(5) . . . . ?
N2 C18 C17 C16 -57.2(5) . . . . ?

_refine_diff_density_max         0.458
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.086

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/n'
_symmetry_int_tables_number      ?
_chemical_absolute_configuration unk

