# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
# 
#######################################################################

data_p-1
_database_code_depnum_ccdc_archive 'CCDC 999231'
_audit_update_record             
;
2014-04-24 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;
#============================================================================== 
# MK-1
#==============================================================================
_audit_creation_date             '23 April 2014'
_audit_creation_method           SHELXL-97

#==============================================================================

#  CHEMICAL DATA

#==============================================================================

_chemical_name_systematic        
; 
1-(2,5-di-tert-butylphenyl)-1,2,3,4-tetrahydroquinoline  
;
_chemical_name_common            
;

;
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H31 N'
_chemical_formula_sum            'C23 H31 N'
_chemical_formula_weight         321.49
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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'

#==============================================================================

#   CRYSTAL DATA

#==============================================================================

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1      '
_symmetry_space_group_name_Hall  '-P 1 '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3731(10)
_cell_length_b                   9.7689(10)
_cell_length_c                   11.5285(12)
_cell_angle_alpha                85.6050(10)
_cell_angle_beta                 74.3180(10)
_cell_angle_gamma                69.6920(10)
_cell_volume                     952.97(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    90
_cell_measurement_reflns_used    4157
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.56
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9880
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_special_details           
; 
 ? 
;

#==============================================================================

#   EXPERIMENTAL DATA

#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            9262
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3354
_reflns_number_gt                2968
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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     
'calc w=1/[σ²(Fo²)+(0.0428P)²+0.3069P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3354
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.41024(14) 0.74871(13) 0.29397(10) 0.0174(3) Uani 1 1 d . . .
H1A H 0.4007 0.8049 0.2196 0.021 Uiso 1 1 calc R . .
H1B H 0.4973 0.6546 0.2714 0.021 Uiso 1 1 calc R . .
C2 C 0.44796(14) 0.83346(13) 0.37981(11) 0.0195(3) Uani 1 1 d . . .
H2A H 0.3618 0.9282 0.4018 0.023 Uiso 1 1 calc R . .
H2B H 0.5464 0.8532 0.3399 0.023 Uiso 1 1 calc R . .
C3 C 0.46732(14) 0.74541(13) 0.49305(11) 0.0201(3) Uani 1 1 d . . .
H3A H 0.5696 0.6644 0.4742 0.024 Uiso 1 1 calc R . .
H3B H 0.4684 0.8089 0.5555 0.024 Uiso 1 1 calc R . .
C4 C 0.33569(14) 0.68352(12) 0.54196(10) 0.0167(3) Uani 1 1 d . . .
C5 C 0.30428(14) 0.63931(13) 0.66117(11) 0.0193(3) Uani 1 1 d . . .
H5 H 0.3647 0.6516 0.7112 0.023 Uiso 1 1 calc R . .
C6 C 0.18856(14) 0.57813(13) 0.70982(11) 0.0208(3) Uani 1 1 d . . .
H6 H 0.1703 0.5487 0.7914 0.025 Uiso 1 1 calc R . .
C7 C 0.09978(14) 0.56067(13) 0.63682(11) 0.0204(3) Uani 1 1 d . . .
H7 H 0.0205 0.5181 0.6682 0.024 Uiso 1 1 calc R . .
C8 C 0.12665(14) 0.60525(13) 0.51810(11) 0.0182(3) Uani 1 1 d . . .
H8 H 0.0645 0.5934 0.4693 0.022 Uiso 1 1 calc R . .
C9 C 0.24381(13) 0.66752(12) 0.46858(10) 0.0156(3) Uani 1 1 d . . .
C10 C 0.21146(13) 0.65919(13) 0.26489(10) 0.0154(3) Uani 1 1 d . . .
C11 C 0.08793(13) 0.74306(12) 0.21391(10) 0.0161(3) Uani 1 1 d . . .
C12 C 0.06428(14) 0.67178(13) 0.12363(10) 0.0181(3) Uani 1 1 d . . .
H12 H -0.0163 0.7243 0.0855 0.022 Uiso 1 1 calc R . .
C13 C 0.15260(14) 0.52830(13) 0.08702(10) 0.0174(3) Uani 1 1 d . . .
H13 H 0.1319 0.4865 0.0244 0.021 Uiso 1 1 calc R . .
C14 C 0.27083(13) 0.44439(12) 0.14010(10) 0.0154(3) Uani 1 1 d . . .
C15 C 0.29695(13) 0.51460(13) 0.22928(10) 0.0154(3) Uani 1 1 d . . .
H15 H 0.3770 0.4609 0.2675 0.019 Uiso 1 1 calc R . .
C16 C -0.01778(14) 0.90097(13) 0.25372(11) 0.0192(3) Uani 1 1 d . . .
C17 C 0.07931(15) 1.00322(13) 0.23225(12) 0.0251(3) Uani 1 1 d . . .
H17A H 0.1508 0.9762 0.2849 0.038 Uiso 1 1 calc R . .
H17B H 0.0083 1.1042 0.2502 0.038 Uiso 1 1 calc R . .
H17C H 0.1408 0.9945 0.1479 0.038 Uiso 1 1 calc R . .
C18 C -0.10409(15) 0.90656(14) 0.38838(11) 0.0258(3) Uani 1 1 d . . .
H18A H -0.0267 0.8745 0.4362 0.039 Uiso 1 1 calc R . .
H18B H -0.1668 0.8419 0.4025 0.039 Uiso 1 1 calc R . .
H18C H -0.1737 1.0068 0.4121 0.039 Uiso 1 1 calc R . .
C19 C -0.14446(15) 0.96202(14) 0.18389(12) 0.0247(3) Uani 1 1 d . . .
H19A H -0.2102 1.0618 0.2124 0.037 Uiso 1 1 calc R . .
H19B H -0.2104 0.9004 0.1971 0.037 Uiso 1 1 calc R . .
H19C H -0.0935 0.9627 0.0977 0.037 Uiso 1 1 calc R . .
C20 C 0.37135(14) 0.28517(13) 0.10439(10) 0.0173(3) Uani 1 1 d . . .
C21 C 0.36365(15) 0.19006(13) 0.21719(11) 0.0222(3) Uani 1 1 d . . .
H21A H 0.4063 0.2231 0.2742 0.033 Uiso 1 1 calc R . .
H21B H 0.4259 0.0879 0.1939 0.033 Uiso 1 1 calc R . .
H21C H 0.2538 0.1987 0.2552 0.033 Uiso 1 1 calc R . .
C22 C 0.54303(14) 0.27538(13) 0.04686(11) 0.0207(3) Uani 1 1 d . . .
H22A H 0.5479 0.3360 -0.0249 0.031 Uiso 1 1 calc R . .
H22B H 0.6079 0.1737 0.0238 0.031 Uiso 1 1 calc R . .
H22C H 0.5828 0.3102 0.1050 0.031 Uiso 1 1 calc R . .
C23 C 0.31299(15) 0.22517(13) 0.01382(11) 0.0215(3) Uani 1 1 d . . .
H23A H 0.2033 0.2315 0.0494 0.032 Uiso 1 1 calc R . .
H23B H 0.3788 0.1230 -0.0061 0.032 Uiso 1 1 calc R . .
H23C H 0.3196 0.2828 -0.0596 0.032 Uiso 1 1 calc R . .
N1 N 0.26206(11) 0.72119(10) 0.35044(8) 0.0154(2) 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
C1 N1 1.4727(15) . ?
C1 C2 1.5191(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.5247(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5150(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.3930(17) . ?
C4 C9 1.4104(16) . ?
C5 C6 1.3850(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.3888(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3873(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.4049(17) . ?
C8 H8 0.9500 . ?
C9 N1 1.4092(15) . ?
C10 C15 1.3897(16) . ?
C10 C11 1.4117(16) . ?
C10 N1 1.4520(14) . ?
C11 C12 1.4001(16) . ?
C11 C16 1.5407(16) . ?
C12 C13 1.3872(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3905(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.3957(16) . ?
C14 C20 1.5323(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.5358(17) . ?
C16 C19 1.5380(17) . ?
C16 C18 1.5398(17) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C23 1.5355(16) . ?
C20 C22 1.5377(17) . ?
C20 C21 1.5396(16) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
N1 C1 C2 110.67(9) . . ?
N1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C1 C2 C3 109.72(10) . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 C2 111.78(10) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C9 118.51(11) . . ?
C5 C4 C3 120.16(10) . . ?
C9 C4 C3 121.33(10) . . ?
C6 C5 C4 122.72(11) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C5 C6 C7 118.61(11) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C8 C7 C6 120.15(11) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 121.35(11) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 N1 120.45(10) . . ?
C8 C9 C4 118.65(11) . . ?
N1 C9 C4 120.78(10) . . ?
C15 C10 C11 120.96(10) . . ?
C15 C10 N1 116.79(10) . . ?
C11 C10 N1 122.14(10) . . ?
C12 C11 C10 115.20(10) . . ?
C12 C11 C16 120.90(10) . . ?
C10 C11 C16 123.89(10) . . ?
C13 C12 C11 123.30(11) . . ?
C13 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
C12 C13 C14 121.39(11) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C15 115.92(11) . . ?
C13 C14 C20 123.83(10) . . ?
C15 C14 C20 120.24(10) . . ?
C10 C15 C14 123.18(11) . . ?
C10 C15 H15 118.4 . . ?
C14 C15 H15 118.4 . . ?
C17 C16 C19 107.25(10) . . ?
C17 C16 C18 109.14(10) . . ?
C19 C16 C18 107.22(10) . . ?
C17 C16 C11 111.17(10) . . ?
C19 C16 C11 111.81(10) . . ?
C18 C16 C11 110.11(10) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 C23 111.64(10) . . ?
C14 C20 C22 109.13(9) . . ?
C23 C20 C22 108.77(10) . . ?
C14 C20 C21 109.58(9) . . ?
C23 C20 C21 108.21(9) . . ?
C22 C20 C21 109.49(10) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C9 N1 C10 118.45(9) . . ?
C9 N1 C1 116.88(9) . . ?
C10 N1 C1 111.76(9) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.039
