# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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_abdellah18_0m
_database_code_depnum_ccdc_archive 'CCDC 1835022'
_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4-(1,1-diphenylethyl)-N,N-dimethylaniline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 N'
_chemical_formula_sum            'C22 H23 N'
_chemical_formula_weight         301.41

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'

_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                   9.7438(15)
_cell_length_b                   9.9224(16)
_cell_length_c                   10.9840(19)
_cell_angle_alpha                64.086(6)
_cell_angle_beta                 78.354(7)
_cell_angle_gamma                63.503(6)
_cell_volume                     854.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3554
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      30.47

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11817
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.637
_diffrn_reflns_theta_max         30.604
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             4797
_reflns_number_gt                3253
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1124P)²+1.2628P] 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         4797
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0778
_refine_ls_wR_factor_ref         0.2795
_refine_ls_wR_factor_gt          0.2647
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_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_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
C1 C 0.4179(3) 0.3223(3) 0.3559(3) 0.0193(5) Uani 1 1 d . . . . .
C3 C 0.3631(3) 0.2962(3) 0.5026(3) 0.0192(5) Uani 1 1 d . . . . .
C6 C 0.2509(3) 0.2614(3) 0.7709(3) 0.0205(5) Uani 1 1 d . . . . .
C9 C 0.5926(3) 0.2611(3) 0.3468(3) 0.0197(5) Uani 1 1 d . . . . .
C4 C 0.2084(3) 0.3333(3) 0.5368(3) 0.0220(5) Uani 1 1 d . . . . .
H4 H 0.1386 0.3712 0.4681 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4601(3) 0.2377(3) 0.6075(3) 0.0210(5) Uani 1 1 d . . . . .
H8 H 0.5668 0.2085 0.5892 0.025 Uiso 1 1 calc R U . . .
C7 C 0.4063(3) 0.2204(3) 0.7385(3) 0.0226(6) Uani 1 1 d . . . . .
H7 H 0.4769 0.1797 0.8073 0.027 Uiso 1 1 calc R U . . .
C15 C 0.3484(3) 0.5057(3) 0.2618(3) 0.0212(5) Uani 1 1 d . . . . .
C5 C 0.1525(3) 0.3172(3) 0.6654(3) 0.0222(5) Uani 1 1 d . . . . .
H5 H 0.0460 0.3442 0.6834 0.027 Uiso 1 1 calc R U . . .
C2 C 0.3636(3) 0.2273(4) 0.3100(3) 0.0254(6) Uani 1 1 d . . . . .
H2A H 0.4153 0.2215 0.2249 0.038 Uiso 1 1 calc R U . . .
H2B H 0.2524 0.2840 0.2962 0.038 Uiso 1 1 calc R U . . .
H2C H 0.3886 0.1160 0.3796 0.038 Uiso 1 1 calc R U . . .
C14 C 0.6873(3) 0.1047(3) 0.3505(3) 0.0246(6) Uani 1 1 d . . . . .
H14 H 0.6428 0.0343 0.3560 0.030 Uiso 1 1 calc R U . . .
C20 C 0.2821(3) 0.6299(3) 0.3093(3) 0.0256(6) Uani 1 1 d . . . . .
H20 H 0.2727 0.6029 0.4040 0.031 Uiso 1 1 calc R U . . .
C10 C 0.6634(3) 0.3603(4) 0.3380(3) 0.0278(6) Uani 1 1 d . . . . .
H10 H 0.6016 0.4681 0.3339 0.033 Uiso 1 1 calc R U . . .
C12 C 0.9131(4) 0.1507(4) 0.3384(3) 0.0312(7) Uani 1 1 d . . . . .
H12 H 1.0216 0.1131 0.3352 0.037 Uiso 1 1 calc R U . . .
C11 C 0.8215(4) 0.3055(4) 0.3351(3) 0.0306(7) Uani 1 1 d . . . . .
H11 H 0.8668 0.3747 0.3308 0.037 Uiso 1 1 calc R U . . .
C18 C 0.2432(4) 0.8360(4) 0.0818(4) 0.0380(8) Uani 1 1 d . . . . .
H18 H 0.2080 0.9480 0.0210 0.046 Uiso 1 1 calc R U . . .
C16 C 0.3604(4) 0.5508(4) 0.1220(3) 0.0295(6) Uani 1 1 d . . . . .
H16 H 0.4047 0.4680 0.0870 0.035 Uiso 1 1 calc R U . . .
C13 C 0.8459(4) 0.0507(4) 0.3463(3) 0.0317(7) Uani 1 1 d . . . . .
H13 H 0.9086 -0.0563 0.3490 0.038 Uiso 1 1 calc R U . . .
C17 C 0.3090(4) 0.7137(4) 0.0335(3) 0.0369(8) Uani 1 1 d . . . . .
H17 H 0.3192 0.7415 -0.0613 0.044 Uiso 1 1 calc R U . . .
C19 C 0.2290(4) 0.7940(4) 0.2193(4) 0.0332(7) Uani 1 1 d . . . . .
H19 H 0.1826 0.8777 0.2534 0.040 Uiso 1 1 calc R U . . .
C21 C 0.0335(4) 0.3276(5) 0.9213(4) 0.0412(8) Uani 1 1 d . . . . .
H21A H 0.0009 0.4467 0.8753 0.062 Uiso 1 1 calc R U . . .
H21B H 0.0112 0.2980 1.0184 0.062 Uiso 1 1 calc R U . . .
H21C H -0.0220 0.2927 0.8841 0.062 Uiso 1 1 calc R U . . .
C22 C 0.2930(4) 0.2338(5) 0.9937(3) 0.0417(8) Uani 1 1 d . . . . .
H22A H 0.3898 0.1371 1.0052 0.062 Uiso 1 1 calc R U . . .
H22B H 0.2408 0.2226 1.0815 0.062 Uiso 1 1 calc R U . . .
H22C H 0.3139 0.3323 0.9569 0.062 Uiso 1 1 calc R U . . .
N1 N 0.1959(3) 0.2473(3) 0.9009(2) 0.0275(5) 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 C9 1.529(4) . ?
C1 C3 1.536(4) . ?
C1 C15 1.541(4) . ?
C1 C2 1.548(4) . ?
C3 C8 1.387(4) . ?
C3 C4 1.395(4) . ?
C6 N1 1.389(4) . ?
C6 C7 1.394(4) . ?
C6 C5 1.409(4) . ?
C9 C14 1.394(4) . ?
C9 C10 1.396(4) . ?
C4 C5 1.374(4) . ?
C4 H4 0.9500 . ?
C8 C7 1.391(4) . ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?
C15 C20 1.388(4) . ?
C15 C16 1.394(4) . ?
C5 H5 0.9500 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C14 C13 1.390(4) . ?
C14 H14 0.9500 . ?
C20 C19 1.394(4) . ?
C20 H20 0.9500 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9500 . ?
C12 C11 1.378(4) . ?
C12 C13 1.379(5) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C18 C19 1.375(5) . ?
C18 C17 1.378(5) . ?
C18 H18 0.9500 . ?
C16 C17 1.382(4) . ?
C16 H16 0.9500 . ?
C13 H13 0.9500 . ?
C17 H17 0.9500 . ?
C19 H19 0.9500 . ?
C21 N1 1.441(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 N1 1.451(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C9 C1 C3 110.4(2) . . ?
C9 C1 C15 108.2(2) . . ?
C3 C1 C15 110.8(2) . . ?
C9 C1 C2 110.7(2) . . ?
C3 C1 C2 107.7(2) . . ?
C15 C1 C2 109.0(2) . . ?
C8 C3 C4 116.1(2) . . ?
C8 C3 C1 123.4(2) . . ?
C4 C3 C1 120.5(2) . . ?
N1 C6 C7 121.7(2) . . ?
N1 C6 C5 121.6(3) . . ?
C7 C6 C5 116.7(2) . . ?
C14 C9 C10 117.4(3) . . ?
C14 C9 C1 122.1(2) . . ?
C10 C9 C1 120.5(2) . . ?
C5 C4 C3 122.9(2) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C3 C8 C7 122.1(3) . . ?
C3 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C20 C15 C16 117.8(2) . . ?
C20 C15 C1 123.0(2) . . ?
C16 C15 C1 119.1(2) . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C13 C14 C9 120.8(3) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C15 C20 C19 120.6(3) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C11 C12 C13 119.4(3) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C19 C18 C17 119.2(3) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C17 C16 C15 121.3(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C12 C13 C14 120.7(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C18 C19 C20 120.7(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C6 N1 C21 118.9(3) . . ?
C6 N1 C22 118.3(3) . . ?
C21 N1 C22 115.1(3) . . ?

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.078



####################################################################### 
# 
# 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_abdellah17_0m
_database_code_depnum_ccdc_archive 'CCDC 1835023'
_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        4-(1,1-diphenylethyl)-N,N-diethylaniline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H27 N'
_chemical_formula_sum            'C24 H27 N'
_chemical_formula_weight         329.46

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'

_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                   8.3046(2)
_cell_length_b                   10.7954(2)
_cell_length_c                   12.0469(2)
_cell_angle_alpha                109.6395(9)
_cell_angle_beta                 100.9597(8)
_cell_angle_gamma                104.3515(9)
_cell_volume                     940.16(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      31.27

_exptl_crystal_description       PLATE
_exptl_crystal_colour            BROWN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   NONE
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24997
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.654
_diffrn_reflns_theta_max         31.274
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6108
_reflns_number_gt                4816
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0654P)²+0.1678P] 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         6108
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1296
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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_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
C6 C 0.67554(11) 0.55795(9) 0.28654(8) 0.01886(17) Uani 1 1 d . . . . .
C1 C 1.12344(11) 0.89611(9) 0.30879(8) 0.01873(17) Uani 1 1 d . . . . .
C3 C 0.96498(11) 0.77671(9) 0.29654(8) 0.01752(17) Uani 1 1 d . . . . .
C9 C 1.06334(11) 1.01042(9) 0.28278(8) 0.01809(17) Uani 1 1 d . . . . .
C4 C 0.98719(11) 0.66499(9) 0.32428(8) 0.01953(17) Uani 1 1 d . . . . .
H4 H 1.1015 0.6616 0.3469 0.023 Uiso 1 1 calc R U . . .
C5 C 0.84842(11) 0.55902(9) 0.31996(9) 0.01983(18) Uani 1 1 d . . . . .
H5 H 0.8702 0.4855 0.3399 0.024 Uiso 1 1 calc R U . . .
C7 C 0.65284(11) 0.66938(10) 0.25725(9) 0.02210(19) Uani 1 1 d . . . . .
H7 H 0.5387 0.6726 0.2331 0.027 Uiso 1 1 calc R U . . .
C8 C 0.79394(11) 0.77484(10) 0.26296(9) 0.02074(18) Uani 1 1 d . . . . .
H8 H 0.7730 0.8487 0.2432 0.025 Uiso 1 1 calc R U . . .
C11 C 0.92272(12) 1.08316(10) 0.13117(9) 0.02279(19) Uani 1 1 d . . . . .
H11 H 0.8683 1.0640 0.0475 0.027 Uiso 1 1 calc R U . . .
C15 C 1.22248(11) 0.84674(10) 0.21575(9) 0.02084(18) Uani 1 1 d . . . . .
C14 C 1.07900(12) 1.13584(10) 0.37544(9) 0.02336(19) Uani 1 1 d . . . . .
H14 H 1.1316 1.1550 0.4594 0.028 Uiso 1 1 calc R U . . .
C21 C 0.55642(13) 0.33092(10) 0.30000(10) 0.0258(2) Uani 1 1 d . . . . .
H21A H 0.6480 0.3065 0.2643 0.031 Uiso 1 1 calc R U . . .
H21B H 0.4459 0.2518 0.2536 0.031 Uiso 1 1 calc R U . . .
C12 C 0.94112(13) 1.20835(10) 0.22454(10) 0.0253(2) Uani 1 1 d . . . . .
H12 H 0.9012 1.2760 0.2052 0.030 Uiso 1 1 calc R U . . .
C10 C 0.98401(11) 0.98606(10) 0.16027(9) 0.02063(18) Uani 1 1 d . . . . .
H10 H 0.9719 0.9011 0.0956 0.025 Uiso 1 1 calc R U . . .
C20 C 1.16062(12) 0.71546(11) 0.11926(9) 0.0251(2) Uani 1 1 d . . . . .
H20 H 1.0566 0.6483 0.1126 0.030 Uiso 1 1 calc R U . . .
C23 C 0.35915(12) 0.45463(11) 0.24894(10) 0.0253(2) Uani 1 1 d . . . . .
H23A H 0.3606 0.5524 0.2796 0.030 Uiso 1 1 calc R U . . .
H23B H 0.2895 0.4058 0.2894 0.030 Uiso 1 1 calc R U . . .
C2 C 1.24796(12) 0.95524(11) 0.44181(9) 0.0267(2) Uani 1 1 d . . . . .
H2A H 1.1830 0.9784 0.5013 0.040 Uiso 1 1 calc R U . . .
H2B H 1.3419 1.0397 0.4560 0.040 Uiso 1 1 calc R U . . .
H2C H 1.2978 0.8851 0.4523 0.040 Uiso 1 1 calc R U . . .
C13 C 1.01798(14) 1.23375(11) 0.34589(10) 0.0277(2) Uani 1 1 d . . . . .
H13 H 1.0295 1.3189 0.4101 0.033 Uiso 1 1 calc R U . . .
C16 C 1.37755(13) 0.94191(11) 0.22299(12) 0.0303(2) Uani 1 1 d . . . . .
H16 H 1.4238 1.0321 0.2887 0.036 Uiso 1 1 calc R U . . .
C19 C 1.24897(15) 0.68052(13) 0.03184(10) 0.0319(2) Uani 1 1 d . . . . .
H19 H 1.2043 0.5902 -0.0337 0.038 Uiso 1 1 calc R U . . .
C18 C 1.40066(15) 0.77623(14) 0.04004(12) 0.0361(3) Uani 1 1 d . . . . .
H18 H 1.4603 0.7525 -0.0196 0.043 Uiso 1 1 calc R U . . .
C17 C 1.46485(14) 0.90697(14) 0.13605(13) 0.0375(3) Uani 1 1 d . . . . .
H17 H 1.5695 0.9734 0.1425 0.045 Uiso 1 1 calc R U . . .
C22 C 0.60457(16) 0.35038(12) 0.43458(11) 0.0364(3) Uani 1 1 d . . . . .
H22A H 0.7122 0.4303 0.4816 0.055 Uiso 1 1 calc R U . . .
H22B H 0.6223 0.2659 0.4400 0.055 Uiso 1 1 calc R U . . .
H22C H 0.5103 0.3675 0.4688 0.055 Uiso 1 1 calc R U . . .
C24 C 0.27178(15) 0.38490(13) 0.11063(11) 0.0371(3) Uani 1 1 d . . . . .
H24A H 0.3401 0.4326 0.0698 0.056 Uiso 1 1 calc R U . . .
H24B H 0.1542 0.3903 0.0925 0.056 Uiso 1 1 calc R U . . .
H24C H 0.2645 0.2867 0.0802 0.056 Uiso 1 1 calc R U . . .
N1 N 0.53645(10) 0.45454(9) 0.28414(8) 0.02539(18) 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
C6 N1 1.3812(11) . ?
C6 C7 1.4069(12) . ?
C6 C5 1.4115(12) . ?
C1 C3 1.5403(12) . ?
C1 C9 1.5413(12) . ?
C1 C15 1.5438(13) . ?
C1 C2 1.5492(13) . ?
C3 C8 1.3941(11) . ?
C3 C4 1.3993(12) . ?
C9 C14 1.3920(13) . ?
C9 C10 1.4018(12) . ?
C4 C5 1.3868(12) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C7 C8 1.3890(12) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C11 C10 1.3872(12) . ?
C11 C12 1.3876(14) . ?
C11 H11 0.9500 . ?
C15 C20 1.3886(14) . ?
C15 C16 1.4010(13) . ?
C14 C13 1.3967(13) . ?
C14 H14 0.9500 . ?
C21 N1 1.4540(12) . ?
C21 C22 1.5217(15) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C12 C13 1.3815(15) . ?
C12 H12 0.9500 . ?
C10 H10 0.9500 . ?
C20 C19 1.3978(15) . ?
C20 H20 0.9500 . ?
C23 N1 1.4531(12) . ?
C23 C24 1.5151(15) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C13 H13 0.9500 . ?
C16 C17 1.3869(16) . ?
C16 H16 0.9500 . ?
C19 C18 1.3796(17) . ?
C19 H19 0.9500 . ?
C18 C17 1.3817(19) . ?
C18 H18 0.9500 . ?
C17 H17 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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 C6 C7 121.73(8) . . ?
N1 C6 C5 122.06(8) . . ?
C7 C6 C5 116.21(8) . . ?
C3 C1 C9 109.99(7) . . ?
C3 C1 C15 112.51(7) . . ?
C9 C1 C15 106.69(7) . . ?
C3 C1 C2 107.70(7) . . ?
C9 C1 C2 110.90(8) . . ?
C15 C1 C2 109.09(7) . . ?
C8 C3 C4 115.96(8) . . ?
C8 C3 C1 123.24(7) . . ?
C4 C3 C1 120.75(7) . . ?
C14 C9 C10 117.90(8) . . ?
C14 C9 C1 123.27(8) . . ?
C10 C9 C1 118.80(8) . . ?
C5 C4 C3 122.41(8) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 121.43(8) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C8 C7 C6 121.34(8) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C3 122.64(8) . . ?
C7 C8 H8 118.7 . . ?
C3 C8 H8 118.7 . . ?
C10 C11 C12 119.83(9) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C20 C15 C16 117.55(9) . . ?
C20 C15 C1 123.62(8) . . ?
C16 C15 C1 118.68(9) . . ?
C9 C14 C13 120.46(9) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
N1 C21 C22 113.08(9) . . ?
N1 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
N1 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C13 C12 C11 119.42(9) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C11 C10 C9 121.54(9) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C15 C20 C19 121.07(10) . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
N1 C23 C24 113.22(9) . . ?
N1 C23 H23A 108.9 . . ?
C24 C23 H23A 108.9 . . ?
N1 C23 H23B 108.9 . . ?
C24 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C12 C13 C14 120.85(9) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C17 C16 C15 121.24(11) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C18 C19 C20 120.44(11) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C18 C17 119.25(10) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C17 C16 120.44(10) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C6 N1 C23 121.36(8) . . ?
C6 N1 C21 121.79(8) . . ?
C23 N1 C21 116.33(8) . . ?

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.044

_shelxl_version_number           2014-3



