# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1025142'
_audit_update_record             
;
2014-09-18 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'DAC-COPh-Cl-HCl Cation'
_chemical_melting_point          ?
_chemical_formula_moiety         {(C24H28N2O2)-(COC6H5)-Cl}-HCl
_chemical_formula_sum            'C31 H34 Cl2 N2 O3'
_chemical_formula_weight         553.50

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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.4917(7)
_cell_length_b                   18.4515(14)
_cell_length_c                   16.3576(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.110(2)
_cell_angle_gamma                90
_cell_volume                     2820.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    0.265
_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   none
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52026
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.036
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4961
_reflns_number_gt                4546
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0336P)²+2.7157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4961
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.002
_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
O1 O 1.07114(12) -0.00571(6) 0.12671(7) 0.0197(3) Uani 1 1 d . . . . .
N1 N 0.88453(14) 0.04676(7) 0.17515(8) 0.0128(3) Uani 1 1 d . . . . .
C1 C 0.82383(16) 0.10589(8) 0.20077(9) 0.0131(3) Uani 1 1 d . . . . .
Cl1 Cl 1.23033(6) 0.16042(3) 0.51618(3) 0.03824(14) Uani 1 1 d . . . . .
H1A H 1.210(3) 0.1333(15) 0.4420(16) 0.062(8) Uiso 1 1 d . . . . .
N2 N 0.87502(14) 0.17255(7) 0.19536(8) 0.0137(3) Uani 1 1 d . . . . .
O2 O 1.05263(13) 0.24654(6) 0.16726(8) 0.0246(3) Uani 1 1 d . . . . .
C2 C 0.68181(17) 0.09757(8) 0.23431(10) 0.0149(3) Uani 1 1 d . . . . .
Cl2 Cl 1.17994(4) 0.09215(2) 0.32874(3) 0.02243(11) Uani 1 1 d . . . . .
O3 O 0.57354(12) 0.09604(6) 0.18247(7) 0.0206(3) Uani 1 1 d . . . . .
C3 C 1.01744(17) 0.05003(9) 0.14245(9) 0.0149(3) Uani 1 1 d . . . . .
C4 C 1.06728(17) 0.12431(9) 0.12077(9) 0.0160(3) Uani 1 1 d . . . . .
C5 C 1.00704(17) 0.18616(9) 0.16420(9) 0.0162(3) Uani 1 1 d . . . . .
C6 C 1.0046(2) 0.13619(10) 0.02708(10) 0.0227(4) Uani 1 1 d . . . . .
H6A H 0.9020 0.1358 0.0193 0.034 Uiso 1 1 calc R U . . .
H6B H 1.0367 0.0980 -0.0051 0.034 Uiso 1 1 calc R U . . .
H6C H 1.0366 0.1820 0.0094 0.034 Uiso 1 1 calc R U . . .
C7 C 1.23059(18) 0.12918(10) 0.13285(11) 0.0229(4) Uani 1 1 d . . . . .
H7A H 1.2700 0.1249 0.1908 0.034 Uiso 1 1 calc R U . . .
H7B H 1.2576 0.1750 0.1125 0.034 Uiso 1 1 calc R U . . .
H7C H 1.2665 0.0907 0.1028 0.034 Uiso 1 1 calc R U . . .
C11 C 0.81021(16) -0.02371(8) 0.17080(10) 0.0141(3) Uani 1 1 d . . . . .
C12 C 0.83854(17) -0.07335(9) 0.23578(10) 0.0157(3) Uani 1 1 d . . . . .
C13 C 0.75914(18) -0.13767(9) 0.22695(10) 0.0184(3) Uani 1 1 d . . . . .
H13A H 0.7710 -0.1702 0.2710 0.022 Uiso 1 1 calc R U . . .
C14 C 0.66384(18) -0.15497(9) 0.15555(11) 0.0189(4) Uani 1 1 d . . . . .
C15 C 0.64557(17) -0.10537(9) 0.09011(10) 0.0174(3) Uani 1 1 d . . . . .
H15A H 0.5845 -0.1170 0.0410 0.021 Uiso 1 1 calc R U . . .
C16 C 0.71633(17) -0.03898(9) 0.09637(10) 0.0152(3) Uani 1 1 d . . . . .
C17 C 0.95117(19) -0.06389(9) 0.31191(10) 0.0211(4) Uani 1 1 d . . . . .
H17A H 1.0070 -0.0215 0.3057 0.032 Uiso 1 1 calc R U . . .
H17B H 1.0124 -0.1057 0.3189 0.032 Uiso 1 1 calc R U . . .
H17C H 0.9061 -0.0585 0.3597 0.032 Uiso 1 1 calc R U . . .
C18 C 0.5855(2) -0.22646(9) 0.14822(12) 0.0258(4) Uani 1 1 d . . . . .
H18A H 0.5879 -0.2466 0.2026 0.039 Uiso 1 1 calc R U . . .
H18B H 0.6309 -0.2593 0.1155 0.039 Uiso 1 1 calc R U . . .
H18C H 0.4880 -0.2190 0.1220 0.039 Uiso 1 1 calc R U . . .
C19 C 0.69397(18) 0.01328(9) 0.02445(10) 0.0187(4) Uani 1 1 d . . . . .
H19A H 0.6225 -0.0056 -0.0192 0.028 Uiso 1 1 calc R U . . .
H19B H 0.7823 0.0196 0.0043 0.028 Uiso 1 1 calc R U . . .
H19C H 0.6628 0.0592 0.0425 0.028 Uiso 1 1 calc R U . . .
C21 C 0.79711(17) 0.23722(8) 0.21591(10) 0.0153(3) Uani 1 1 d . . . . .
C22 C 0.68720(18) 0.26428(9) 0.15492(10) 0.0196(4) Uani 1 1 d . . . . .
C23 C 0.62075(18) 0.32827(9) 0.17258(11) 0.0209(4) Uani 1 1 d . . . . .
H23A H 0.5447 0.3461 0.1341 0.025 Uiso 1 1 calc R U . . .
C24 C 0.66478(18) 0.36642(9) 0.24614(11) 0.0193(4) Uani 1 1 d . . . . .
C25 C 0.77623(18) 0.33820(9) 0.30336(10) 0.0181(3) Uani 1 1 d . . . . .
H25A H 0.8060 0.3632 0.3527 0.022 Uiso 1 1 calc R U . . .
C26 C 0.84565(17) 0.27381(9) 0.29000(10) 0.0163(3) Uani 1 1 d . . . . .
C27 C 0.6437(2) 0.22976(10) 0.07069(11) 0.0292(4) Uani 1 1 d . . . . .
H27A H 0.5655 0.2564 0.0394 0.044 Uiso 1 1 calc R U . . .
H27B H 0.6146 0.1806 0.0774 0.044 Uiso 1 1 calc R U . . .
H27C H 0.7234 0.2303 0.0417 0.044 Uiso 1 1 calc R U . . .
C28 C 0.5986(2) 0.43864(9) 0.26052(12) 0.0253(4) Uani 1 1 d . . . . .
H28A H 0.5995 0.4451 0.3188 0.038 Uiso 1 1 calc R U . . .
H28B H 0.5017 0.4400 0.2312 0.038 Uiso 1 1 calc R U . . .
H28C H 0.6525 0.4768 0.2406 0.038 Uiso 1 1 calc R U . . .
C29 C 0.97072(18) 0.24886(9) 0.35313(10) 0.0200(4) Uani 1 1 d . . . . .
H29A H 1.0197 0.2106 0.3300 0.030 Uiso 1 1 calc R U . . .
H29B H 0.9371 0.2314 0.4016 0.030 Uiso 1 1 calc R U . . .
H29C H 1.0352 0.2887 0.3682 0.030 Uiso 1 1 calc R U . . .
C31 C 0.69152(17) 0.09183(8) 0.32444(10) 0.0153(3) Uani 1 1 d . . . . .
C32 C 0.56487(18) 0.08807(9) 0.35749(11) 0.0196(4) Uani 1 1 d . . . . .
H32A H 0.4764 0.0922 0.3228 0.024 Uiso 1 1 calc R U . . .
C33 C 0.5726(2) 0.07825(10) 0.44175(12) 0.0266(4) Uani 1 1 d . . . . .
H33A H 0.4890 0.0759 0.4640 0.032 Uiso 1 1 calc R U . . .
C34 C 0.7051(2) 0.07181(11) 0.49361(11) 0.0289(4) Uani 1 1 d . . . . .
H34A H 0.7094 0.0638 0.5501 0.035 Uiso 1 1 calc R U . . .
C35 C 0.8305(2) 0.07725(10) 0.46159(11) 0.0258(4) Uani 1 1 d . . . . .
H35A H 0.9187 0.0741 0.4967 0.031 Uiso 1 1 calc R U . . .
C36 C 0.82415(18) 0.08739(9) 0.37702(10) 0.0189(4) Uani 1 1 d . . . . .
H36A H 0.9081 0.0912 0.3553 0.023 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
O1 C3 1.196(2) . ?
N1 C1 1.335(2) . ?
N1 C3 1.455(2) . ?
N1 C11 1.475(2) . ?
C1 N2 1.331(2) . ?
C1 C2 1.550(2) . ?
Cl1 H1A 1.30(3) . ?
N2 C5 1.455(2) . ?
N2 C21 1.473(2) . ?
O2 C5 1.193(2) . ?
C2 O3 1.2125(19) . ?
C2 C31 1.465(2) . ?
C3 C4 1.512(2) . ?
C4 C5 1.509(2) . ?
C4 C7 1.530(2) . ?
C4 C6 1.559(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C11 C12 1.393(2) . ?
C11 C16 1.405(2) . ?
C12 C13 1.400(2) . ?
C12 C17 1.502(2) . ?
C13 C14 1.383(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.396(2) . ?
C14 C18 1.509(2) . ?
C15 C16 1.392(2) . ?
C15 H15A 0.9300 . ?
C16 C19 1.507(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 C26 1.393(2) . ?
C21 C22 1.403(2) . ?
C22 C23 1.393(2) . ?
C22 C27 1.508(2) . ?
C23 C24 1.393(2) . ?
C23 H23A 0.9300 . ?
C24 C25 1.385(2) . ?
C24 C28 1.509(2) . ?
C25 C26 1.394(2) . ?
C25 H25A 0.9300 . ?
C26 C29 1.502(2) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C31 C36 1.397(2) . ?
C31 C32 1.404(2) . ?
C32 C33 1.379(3) . ?
C32 H32A 0.9300 . ?
C33 C34 1.393(3) . ?
C33 H33A 0.9300 . ?
C34 C35 1.386(3) . ?
C34 H34A 0.9300 . ?
C35 C36 1.387(2) . ?
C35 H35A 0.9300 . ?
C36 H36A 0.9300 . ?

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
C1 N1 C3 122.08(13) . . ?
C1 N1 C11 120.43(13) . . ?
C3 N1 C11 117.19(12) . . ?
N2 C1 N1 123.48(14) . . ?
N2 C1 C2 117.74(13) . . ?
N1 C1 C2 118.70(13) . . ?
C1 N2 C5 121.97(13) . . ?
C1 N2 C21 121.97(13) . . ?
C5 N2 C21 115.96(12) . . ?
O3 C2 C31 126.73(15) . . ?
O3 C2 C1 115.97(14) . . ?
C31 C2 C1 117.29(13) . . ?
O1 C3 N1 118.25(14) . . ?
O1 C3 C4 124.48(14) . . ?
N1 C3 C4 116.80(13) . . ?
C5 C4 C3 114.52(13) . . ?
C5 C4 C7 110.72(13) . . ?
C3 C4 C7 111.99(14) . . ?
C5 C4 C6 104.22(13) . . ?
C3 C4 C6 106.07(13) . . ?
C7 C4 C6 108.77(14) . . ?
O2 C5 N2 118.34(15) . . ?
O2 C5 C4 124.15(15) . . ?
N2 C5 C4 117.08(13) . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C11 C16 122.50(15) . . ?
C12 C11 N1 121.07(14) . . ?
C16 C11 N1 116.34(14) . . ?
C11 C12 C13 116.77(15) . . ?
C11 C12 C17 124.75(15) . . ?
C13 C12 C17 118.43(14) . . ?
C14 C13 C12 122.90(15) . . ?
C14 C13 H13A 118.5 . . ?
C12 C13 H13A 118.5 . . ?
C13 C14 C15 118.11(15) . . ?
C13 C14 C18 120.59(16) . . ?
C15 C14 C18 121.28(15) . . ?
C16 C15 C14 121.81(15) . . ?
C16 C15 H15A 119.1 . . ?
C14 C15 H15A 119.1 . . ?
C15 C16 C11 117.68(15) . . ?
C15 C16 C19 120.37(14) . . ?
C11 C16 C19 121.94(14) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 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 . . ?
C26 C21 C22 122.50(15) . . ?
C26 C21 N2 119.23(14) . . ?
C22 C21 N2 117.80(14) . . ?
C23 C22 C21 117.49(15) . . ?
C23 C22 C27 119.09(15) . . ?
C21 C22 C27 123.34(15) . . ?
C22 C23 C24 121.96(16) . . ?
C22 C23 H23A 119.0 . . ?
C24 C23 H23A 119.0 . . ?
C25 C24 C23 118.13(15) . . ?
C25 C24 C28 121.06(16) . . ?
C23 C24 C28 120.71(16) . . ?
C24 C25 C26 122.70(15) . . ?
C24 C25 H25A 118.7 . . ?
C26 C25 H25A 118.7 . . ?
C21 C26 C25 117.14(15) . . ?
C21 C26 C29 123.38(15) . . ?
C25 C26 C29 119.44(14) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C36 C31 C32 120.01(15) . . ?
C36 C31 C2 120.97(15) . . ?
C32 C31 C2 118.97(15) . . ?
C33 C32 C31 119.51(16) . . ?
C33 C32 H32A 120.2 . . ?
C31 C32 H32A 120.2 . . ?
C32 C33 C34 120.23(16) . . ?
C32 C33 H33A 119.9 . . ?
C34 C33 H33A 119.9 . . ?
C35 C34 C33 120.49(17) . . ?
C35 C34 H34A 119.8 . . ?
C33 C34 H34A 119.8 . . ?
C34 C35 C36 119.78(17) . . ?
C34 C35 H35A 120.1 . . ?
C36 C35 H35A 120.1 . . ?
C35 C36 C31 119.94(16) . . ?
C35 C36 H36A 120.0 . . ?
C31 C36 H36A 120.0 . . ?

_refine_diff_density_max         0.713
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.044



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexanes and dichloromethane'
_chemical_properties_physical    Hygroscopic
####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1025143'
_audit_update_record             
;
2014-09-18 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'MAAC-COPh-Cl Cation'
_chemical_melting_point          ?
_chemical_formula_moiety         {(C24H30N2O1)-(COC6H5)}Cl1
_chemical_formula_sum            'C31 H35 Cl N2 O2'
_chemical_formula_weight         503.06

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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.4748(10)
_cell_length_b                   17.8218(17)
_cell_length_c                   15.4388(14)
_cell_angle_alpha                90
_cell_angle_beta                 105.179(7)
_cell_angle_gamma                90
_cell_volume                     2781.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.167
_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   none
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21407
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.047
_diffrn_reflns_theta_max         23.997
_diffrn_reflns_theta_full        23.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4354
_reflns_number_gt                2670
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0120P)²+2.7396P] 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         4354
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.065
_refine_ls_shift/su_mean         0.001

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
Cl1 Cl 0.79466(9) 0.11120(5) 0.02280(6) 0.0586(3) Uani 1 1 d . . . . .
O1 O 1.0384(2) 0.24714(13) -0.10200(15) 0.0482(6) Uani 1 1 d . . . . .
N1 N 1.2172(2) 0.11415(13) 0.10440(15) 0.0289(6) Uani 1 1 d . . . . .
C1 C 1.2317(3) 0.18704(17) 0.10902(19) 0.0289(7) Uani 1 1 d . . . . .
N2 N 1.1709(2) 0.23225(13) 0.03964(16) 0.0315(6) Uani 1 1 d . . . . .
C2 C 1.3106(3) 0.22394(16) 0.1975(2) 0.0320(8) Uani 1 1 d . . . . .
O3 O 1.2463(2) 0.24766(13) 0.24636(15) 0.0465(6) Uani 1 1 d . . . . .
C3 C 1.1271(3) 0.07830(16) 0.02467(19) 0.0347(8) Uani 1 1 d . . . . .
H3A H 1.0388 0.0757 0.0333 0.042 Uiso 1 1 calc R U . . .
H3B H 1.1567 0.0274 0.0190 0.042 Uiso 1 1 calc R U . . .
C4 C 1.1222(3) 0.12111(17) -0.0615(2) 0.0344(8) Uani 1 1 d . . . . .
C5 C 1.1004(3) 0.20361(18) -0.0474(2) 0.0345(8) Uani 1 1 d . . . . .
C6 C 1.2536(3) 0.11369(19) -0.0893(2) 0.0487(9) Uani 1 1 d . . . . .
H6A H 1.3242 0.1357 -0.0439 0.073 Uiso 1 1 calc R U . . .
H6B H 1.2455 0.1391 -0.1453 0.073 Uiso 1 1 calc R U . . .
H6C H 1.2724 0.0616 -0.0959 0.073 Uiso 1 1 calc R U . . .
C7 C 1.0080(3) 0.08979(19) -0.1360(2) 0.0492(9) Uani 1 1 d . . . . .
H7A H 0.9264 0.0959 -0.1195 0.074 Uiso 1 1 calc R U . . .
H7B H 1.0228 0.0375 -0.1445 0.074 Uiso 1 1 calc R U . . .
H7C H 1.0030 0.1164 -0.1909 0.074 Uiso 1 1 calc R U . . .
C11 C 1.2632(3) 0.06542(16) 0.1832(2) 0.0328(8) Uani 1 1 d . . . . .
C12 C 1.3701(3) 0.01767(17) 0.1878(2) 0.0398(8) Uani 1 1 d . . . . .
C13 C 1.4032(3) -0.03169(18) 0.2602(2) 0.0500(10) Uani 1 1 d . . . . .
H13A H 1.4761 -0.0629 0.2662 0.060 Uiso 1 1 calc R U . . .
C14 C 1.3315(4) -0.03585(19) 0.3236(2) 0.0477(10) Uani 1 1 d . . . . .
C15 C 1.2249(3) 0.01216(18) 0.3153(2) 0.0423(9) Uani 1 1 d . . . . .
H15A H 1.1774 0.0101 0.3584 0.051 Uiso 1 1 calc R U . . .
C16 C 1.1860(3) 0.06324(17) 0.2453(2) 0.0349(8) Uani 1 1 d . . . . .
C17 C 1.4478(3) 0.01419(19) 0.1180(2) 0.0537(10) Uani 1 1 d . . . . .
H17A H 1.5390 0.0255 0.1456 0.081 Uiso 1 1 calc R U . . .
H17B H 1.4127 0.0501 0.0715 0.081 Uiso 1 1 calc R U . . .
H17C H 1.4410 -0.0353 0.0926 0.081 Uiso 1 1 calc R U . . .
C18 C 1.3667(4) -0.0925(2) 0.3993(3) 0.0746(13) Uani 1 1 d . . . . .
H18A H 1.4069 -0.1356 0.3801 0.112 Uiso 1 1 calc R U . . .
H18B H 1.2879 -0.1075 0.4154 0.112 Uiso 1 1 calc R U . . .
H18C H 1.4275 -0.0702 0.4503 0.112 Uiso 1 1 calc R U . . .
C19 C 1.0633(3) 0.10982(18) 0.2381(2) 0.0433(9) Uani 1 1 d . . . . .
H19A H 1.0046 0.0837 0.2661 0.065 Uiso 1 1 calc R U . . .
H19B H 1.0197 0.1183 0.1760 0.065 Uiso 1 1 calc R U . . .
H19C H 1.0876 0.1571 0.2675 0.065 Uiso 1 1 calc R U . . .
C21 C 1.1741(3) 0.31362(16) 0.0534(2) 0.0341(8) Uani 1 1 d . . . . .
C22 C 1.2660(3) 0.35602(17) 0.0230(2) 0.0334(8) Uani 1 1 d . . . . .
C23 C 1.2739(3) 0.43214(18) 0.0438(2) 0.0430(9) Uani 1 1 d . . . . .
H23A H 1.3359 0.4613 0.0257 0.052 Uiso 1 1 calc R U . . .
C24 C 1.1928(4) 0.46634(19) 0.0904(2) 0.0534(10) Uani 1 1 d . . . . .
C25 C 1.0973(4) 0.42224(19) 0.1133(2) 0.0539(10) Uani 1 1 d . . . . .
H25A H 1.0396 0.4448 0.1421 0.065 Uiso 1 1 calc R U . . .
C26 C 1.0839(3) 0.34551(18) 0.0950(2) 0.0417(9) Uani 1 1 d . . . . .
C27 C 1.3499(3) 0.32227(18) -0.0333(2) 0.0430(9) Uani 1 1 d . . . . .
H27A H 1.3965 0.3615 -0.0548 0.064 Uiso 1 1 calc R U . . .
H27B H 1.2941 0.2960 -0.0834 0.064 Uiso 1 1 calc R U . . .
H27C H 1.4125 0.2879 0.0026 0.064 Uiso 1 1 calc R U . . .
C28 C 1.2082(5) 0.5490(2) 0.1155(3) 0.0861(15) Uani 1 1 d . . . . .
H28A H 1.2240 0.5542 0.1793 0.129 Uiso 1 1 calc R U . . .
H28B H 1.1289 0.5754 0.0860 0.129 Uiso 1 1 calc R U . . .
H28C H 1.2816 0.5696 0.0969 0.129 Uiso 1 1 calc R U . . .
C29 C 0.9746(3) 0.3011(2) 0.1174(3) 0.0571(10) Uani 1 1 d . . . . .
H29A H 0.9052 0.3345 0.1228 0.086 Uiso 1 1 calc R U . . .
H29B H 1.0086 0.2751 0.1731 0.086 Uiso 1 1 calc R U . . .
H29C H 0.9402 0.2654 0.0705 0.086 Uiso 1 1 calc R U . . .
C31 C 1.4560(3) 0.22890(17) 0.2175(2) 0.0332(8) Uani 1 1 d . . . . .
C32 C 1.5271(3) 0.20143(17) 0.1597(2) 0.0392(8) Uani 1 1 d . . . . .
H32A H 1.4824 0.1801 0.1053 0.047 Uiso 1 1 calc R U . . .
C33 C 1.6638(3) 0.2057(2) 0.1828(2) 0.0516(10) Uani 1 1 d . . . . .
H33A H 1.7110 0.1869 0.1442 0.062 Uiso 1 1 calc R U . . .
C34 C 1.7293(3) 0.2380(2) 0.2630(3) 0.0568(11) Uani 1 1 d . . . . .
H34A H 1.8211 0.2406 0.2788 0.068 Uiso 1 1 calc R U . . .
C35 C 1.6599(4) 0.2666(2) 0.3208(2) 0.0546(10) Uani 1 1 d . . . . .
H35A H 1.7051 0.2889 0.3745 0.066 Uiso 1 1 calc R U . . .
C36 C 1.5242(3) 0.26217(18) 0.2985(2) 0.0438(9) Uani 1 1 d . . . . .
H36A H 1.4777 0.2813 0.3373 0.053 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
O1 C5 1.203(3) . ?
N1 C1 1.308(4) . ?
N1 C11 1.469(4) . ?
N1 C3 1.485(3) . ?
C1 N2 1.358(4) . ?
C1 C2 1.546(4) . ?
N2 C5 1.446(4) . ?
N2 C21 1.465(4) . ?
C2 O3 1.211(3) . ?
C2 C31 1.476(4) . ?
C3 C4 1.523(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.513(4) . ?
C4 C7 1.532(4) . ?
C4 C6 1.550(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C11 C12 1.393(4) . ?
C11 C16 1.408(4) . ?
C12 C13 1.393(4) . ?
C12 C17 1.512(4) . ?
C13 C14 1.383(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.385(5) . ?
C14 C18 1.515(5) . ?
C15 C16 1.390(4) . ?
C15 H15A 0.9300 . ?
C16 C19 1.509(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 C26 1.394(4) . ?
C21 C22 1.398(4) . ?
C22 C23 1.391(4) . ?
C22 C27 1.514(4) . ?
C23 C24 1.390(4) . ?
C23 H23A 0.9300 . ?
C24 C25 1.389(5) . ?
C24 C28 1.521(5) . ?
C25 C26 1.396(4) . ?
C25 H25A 0.9300 . ?
C26 C29 1.505(4) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C31 C32 1.391(4) . ?
C31 C36 1.399(4) . ?
C32 C33 1.384(4) . ?
C32 H32A 0.9300 . ?
C33 C34 1.375(5) . ?
C33 H33A 0.9300 . ?
C34 C35 1.387(5) . ?
C34 H34A 0.9300 . ?
C35 C36 1.374(4) . ?
C35 H35A 0.9300 . ?
C36 H36A 0.9300 . ?

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
C1 N1 C11 122.2(2) . . ?
C1 N1 C3 120.8(2) . . ?
C11 N1 C3 115.6(2) . . ?
N1 C1 N2 121.5(3) . . ?
N1 C1 C2 119.9(3) . . ?
N2 C1 C2 118.4(3) . . ?
C1 N2 C5 122.9(3) . . ?
C1 N2 C21 119.0(2) . . ?
C5 N2 C21 118.1(2) . . ?
O3 C2 C31 124.1(3) . . ?
O3 C2 C1 116.3(3) . . ?
C31 C2 C1 119.6(3) . . ?
N1 C3 C4 112.2(2) . . ?
N1 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
N1 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 109.4(2) . . ?
C5 C4 C7 110.2(3) . . ?
C3 C4 C7 108.3(2) . . ?
C5 C4 C6 107.5(3) . . ?
C3 C4 C6 111.7(3) . . ?
C7 C4 C6 109.7(3) . . ?
O1 C5 N2 118.3(3) . . ?
O1 C5 C4 126.8(3) . . ?
N2 C5 C4 114.7(3) . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C11 C16 123.1(3) . . ?
C12 C11 N1 119.2(3) . . ?
C16 C11 N1 117.2(3) . . ?
C11 C12 C13 117.0(3) . . ?
C11 C12 C17 124.3(3) . . ?
C13 C12 C17 118.6(3) . . ?
C14 C13 C12 122.3(3) . . ?
C14 C13 H13A 118.8 . . ?
C12 C13 H13A 118.8 . . ?
C13 C14 C15 118.4(3) . . ?
C13 C14 C18 120.9(3) . . ?
C15 C14 C18 120.7(4) . . ?
C14 C15 C16 122.8(3) . . ?
C14 C15 H15A 118.6 . . ?
C16 C15 H15A 118.6 . . ?
C15 C16 C11 116.4(3) . . ?
C15 C16 C19 119.3(3) . . ?
C11 C16 C19 124.3(3) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 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 . . ?
C26 C21 C22 122.9(3) . . ?
C26 C21 N2 118.5(3) . . ?
C22 C21 N2 118.6(3) . . ?
C23 C22 C21 117.0(3) . . ?
C23 C22 C27 120.7(3) . . ?
C21 C22 C27 122.2(3) . . ?
C24 C23 C22 122.6(3) . . ?
C24 C23 H23A 118.7 . . ?
C22 C23 H23A 118.7 . . ?
C25 C24 C23 117.5(3) . . ?
C25 C24 C28 121.3(3) . . ?
C23 C24 C28 121.2(3) . . ?
C24 C25 C26 122.9(3) . . ?
C24 C25 H25A 118.5 . . ?
C26 C25 H25A 118.5 . . ?
C21 C26 C25 116.7(3) . . ?
C21 C26 C29 122.6(3) . . ?
C25 C26 C29 120.7(3) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C32 C31 C36 119.2(3) . . ?
C32 C31 C2 122.8(3) . . ?
C36 C31 C2 118.0(3) . . ?
C33 C32 C31 120.5(3) . . ?
C33 C32 H32A 119.8 . . ?
C31 C32 H32A 119.8 . . ?
C34 C33 C32 119.5(3) . . ?
C34 C33 H33A 120.2 . . ?
C32 C33 H33A 120.2 . . ?
C33 C34 C35 120.8(3) . . ?
C33 C34 H34A 119.6 . . ?
C35 C34 H34A 119.6 . . ?
C36 C35 C34 119.9(3) . . ?
C36 C35 H35A 120.0 . . ?
C34 C35 H35A 120.0 . . ?
C35 C36 C31 120.1(3) . . ?
C35 C36 H36A 120.0 . . ?
C31 C36 H36A 120.0 . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.044



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexanes and dichloromethane'
_chemical_properties_physical    Hygroscopic
####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 1025144'
_audit_update_record             
;
2014-09-18 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'IPr-COPh-Cl Cation'
_chemical_melting_point          ?
_chemical_formula_moiety         {(C27H36N2)-(COC6H5)}-CH2Cl3
_chemical_formula_sum            'C35 H43 Cl3 N2 O'
_chemical_formula_weight         614.06

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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 '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                   11.4742(18)
_cell_length_b                   11.8275(19)
_cell_length_c                   12.891(2)
_cell_angle_alpha                81.869(6)
_cell_angle_beta                 87.309(6)
_cell_angle_gamma                88.774(6)
_cell_volume                     1729.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_F_000             652
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.293
_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   none
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13521
_diffrn_reflns_av_unetI/netI     0.1709
_diffrn_reflns_av_R_equivalents  0.1337
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.060
_diffrn_reflns_theta_max         23.999
_diffrn_reflns_theta_full        23.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5427
_reflns_number_gt                2497
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0492P)²+0.8075P] 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         5427
_refine_ls_number_parameters     378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1924
_refine_ls_R_factor_gt           0.0786
_refine_ls_wR_factor_ref         0.1685
_refine_ls_wR_factor_gt          0.1302
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
Cl1 Cl 0.34555(12) 0.34235(12) 0.50741(11) 0.0435(4) Uani 1 1 d . . . . .
Cl2 Cl 0.69297(16) 0.33848(14) 0.36694(12) 0.0675(6) Uani 1 1 d . . . . .
Cl3 Cl 0.56649(16) 0.48220(15) 0.20660(14) 0.0735(6) Uani 1 1 d . . . . .
N2 N 0.7601(3) 0.3394(3) 0.7225(3) 0.0278(11) Uani 1 1 d . . . . .
N1 N 0.6375(3) 0.2035(3) 0.7116(3) 0.0267(10) Uani 1 1 d . . . . .
O3 O 0.8283(4) 0.0590(3) 0.8111(3) 0.0610(13) Uani 1 1 d . . . . .
C3 C 0.6830(4) 0.3805(4) 0.6471(4) 0.0295(13) Uani 1 1 d . . . . .
H3A H 0.6840 0.4524 0.6071 0.035 Uiso 1 1 calc R U . . .
C32 C 0.9698(5) 0.3536(4) 0.6863(4) 0.0334(14) Uani 1 1 d . . . . .
C36 C 0.8707(5) 0.4751(4) 0.8058(4) 0.0307(13) Uani 1 1 d . . . . .
C11 C 0.5772(5) 0.0948(4) 0.7278(4) 0.0313(13) Uani 1 1 d . . . . .
C31 C 0.8706(4) 0.3915(4) 0.7392(4) 0.0283(13) Uani 1 1 d . . . . .
C1 C 0.7304(4) 0.2312(4) 0.7609(4) 0.0271(13) Uani 1 1 d . . . . .
C12 C 0.4786(5) 0.0849(5) 0.7949(4) 0.0358(14) Uani 1 1 d . . . . .
C56 C 0.7563(5) 0.2453(5) 0.9950(4) 0.0433(16) Uani 1 1 d . . . . .
H56A H 0.6884 0.2771 0.9657 0.052 Uiso 1 1 calc R U . . .
C4 C 0.6046(5) 0.2967(4) 0.6417(4) 0.0330(14) Uani 1 1 d . . . . .
H4A H 0.5410 0.3015 0.5991 0.040 Uiso 1 1 calc R U . . .
C14 C 0.4626(6) -0.1087(5) 0.7556(5) 0.0477(16) Uani 1 1 d . . . . .
H14A H 0.4235 -0.1777 0.7659 0.057 Uiso 1 1 calc R U . . .
C16 C 0.6215(5) 0.0074(4) 0.6726(4) 0.0336(14) Uani 1 1 d . . . . .
C2 C 0.8009(4) 0.1505(5) 0.8366(4) 0.0315(14) Uani 1 1 d . . . . .
C42 C 0.7714(6) 0.5494(5) 0.9637(4) 0.0583(19) Uani 1 1 d . . . . .
H42A H 0.8000 0.4814 1.0050 0.088 Uiso 1 1 calc R U . . .
H42B H 0.6958 0.5694 0.9914 0.088 Uiso 1 1 calc R U . . .
H42C H 0.8242 0.6108 0.9661 0.088 Uiso 1 1 calc R U . . .
C15 C 0.5607(5) -0.0958(5) 0.6895(5) 0.0466(16) Uani 1 1 d . . . . .
H15A H 0.5872 -0.1565 0.6556 0.056 Uiso 1 1 calc R U . . .
C35 C 0.9811(5) 0.5168(5) 0.8220(4) 0.0442(16) Uani 1 1 d . . . . .
H35A H 0.9865 0.5722 0.8660 0.053 Uiso 1 1 calc R U . . .
C34 C 1.0807(5) 0.4788(5) 0.7756(5) 0.0510(17) Uani 1 1 d . . . . .
H34A H 1.1525 0.5061 0.7905 0.061 Uiso 1 1 calc R U . . .
C20 C 0.7241(5) 0.0219(5) 0.5954(4) 0.0454(16) Uani 1 1 d . . . . .
H20A H 0.7624 0.0933 0.6032 0.054 Uiso 1 1 calc R U . . .
C51 C 0.8303(5) 0.1828(4) 0.9382(4) 0.0341(14) Uani 1 1 d . . . . .
C55 C 0.7817(7) 0.2616(5) 1.0959(5) 0.0585(19) Uani 1 1 d . . . . .
H55A H 0.7299 0.3021 1.1349 0.070 Uiso 1 1 calc R U . . .
C33 C 1.0754(5) 0.3999(5) 0.7065(5) 0.0460(16) Uani 1 1 d . . . . .
H33A H 1.1437 0.3775 0.6729 0.055 Uiso 1 1 calc R U . . .
C37 C 0.9683(5) 0.2689(5) 0.6078(4) 0.0421(15) Uani 1 1 d . . . . .
H37A H 0.8893 0.2383 0.6112 0.051 Uiso 1 1 calc R U . . .
C40 C 0.7621(5) 0.5281(4) 0.8496(4) 0.0375(14) Uani 1 1 d . . . . .
H40A H 0.6980 0.4750 0.8479 0.045 Uiso 1 1 calc R U . . .
C17 C 0.4288(5) 0.1813(5) 0.8511(4) 0.0426(15) Uani 1 1 d . . . . .
H17A H 0.4815 0.2462 0.8346 0.051 Uiso 1 1 calc R U . . .
C13 C 0.4221(5) -0.0201(5) 0.8066(4) 0.0450(16) Uani 1 1 d . . . . .
H13A H 0.3551 -0.0304 0.8501 0.054 Uiso 1 1 calc R U . . .
C38 C 0.9920(5) 0.3291(5) 0.4961(4) 0.0632(19) Uani 1 1 d . . . . .
H38A H 0.9869 0.2751 0.4476 0.095 Uiso 1 1 calc R U . . .
H38B H 1.0687 0.3609 0.4901 0.095 Uiso 1 1 calc R U . . .
H38C H 0.9352 0.3892 0.4806 0.095 Uiso 1 1 calc R U . . .
C30 C 0.5838(5) 0.4449(5) 0.3426(4) 0.0581(18) Uani 1 1 d . . . . .
H30A H 0.6048 0.5120 0.3725 0.070 Uiso 1 1 calc R U . . .
H30B H 0.5105 0.4171 0.3762 0.070 Uiso 1 1 calc R U . . .
C21 C 0.8144(6) -0.0755(5) 0.6140(5) 0.0625(19) Uani 1 1 d . . . . .
H21A H 0.8367 -0.0842 0.6856 0.094 Uiso 1 1 calc R U . . .
H21B H 0.8818 -0.0580 0.5681 0.094 Uiso 1 1 calc R U . . .
H21C H 0.7811 -0.1453 0.6000 0.094 Uiso 1 1 calc R U . . .
C18 C 0.4230(6) 0.1484(5) 0.9693(5) 0.076(2) Uani 1 1 d . . . . .
H18A H 0.4982 0.1209 0.9921 0.115 Uiso 1 1 calc R U . . .
H18B H 0.3666 0.0894 0.9883 0.115 Uiso 1 1 calc R U . . .
H18C H 0.4005 0.2139 1.0021 0.115 Uiso 1 1 calc R U . . .
C52 C 0.9339(6) 0.1395(5) 0.9821(5) 0.065(2) Uani 1 1 d . . . . .
H52A H 0.9861 0.0985 0.9438 0.078 Uiso 1 1 calc R U . . .
C39 C 1.0514(5) 0.1685(5) 0.6356(5) 0.0636(19) Uani 1 1 d . . . . .
H39A H 1.0372 0.1365 0.7077 0.095 Uiso 1 1 calc R U . . .
H39B H 1.1304 0.1941 0.6253 0.095 Uiso 1 1 calc R U . . .
H39C H 1.0390 0.1113 0.5915 0.095 Uiso 1 1 calc R U . . .
C41 C 0.7308(5) 0.6394(5) 0.7804(4) 0.0559(18) Uani 1 1 d . . . . .
H41A H 0.7158 0.6237 0.7112 0.084 Uiso 1 1 calc R U . . .
H41B H 0.7945 0.6914 0.7766 0.084 Uiso 1 1 calc R U . . .
H41C H 0.6623 0.6731 0.8099 0.084 Uiso 1 1 calc R U . . .
C19 C 0.3095(5) 0.2200(6) 0.8109(5) 0.072(2) Uani 1 1 d . . . . .
H19A H 0.2815 0.2835 0.8444 0.108 Uiso 1 1 calc R U . . .
H19B H 0.2558 0.1582 0.8267 0.108 Uiso 1 1 calc R U . . .
H19C H 0.3162 0.2427 0.7364 0.108 Uiso 1 1 calc R U . . .
C22 C 0.6823(6) 0.0323(5) 0.4832(4) 0.065(2) Uani 1 1 d . . . . .
H22A H 0.6224 0.0903 0.4736 0.097 Uiso 1 1 calc R U . . .
H22B H 0.6515 -0.0394 0.4715 0.097 Uiso 1 1 calc R U . . .
H22C H 0.7466 0.0525 0.4343 0.097 Uiso 1 1 calc R U . . .
C53 C 0.9591(7) 0.1574(6) 1.0820(6) 0.084(3) Uani 1 1 d . . . . .
H53A H 1.0278 0.1283 1.1114 0.100 Uiso 1 1 calc R U . . .
C54 C 0.8820(8) 0.2184(6) 1.1375(5) 0.076(2) Uani 1 1 d . . . . .
H54A H 0.8989 0.2304 1.2049 0.092 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
Cl2 C30 1.763(6) . ?
Cl3 C30 1.765(6) . ?
N2 C1 1.350(6) . ?
N2 C3 1.376(6) . ?
N2 C31 1.460(6) . ?
N1 C1 1.336(6) . ?
N1 C4 1.380(6) . ?
N1 C11 1.457(6) . ?
O3 C2 1.206(5) . ?
C3 C4 1.363(6) . ?
C3 H3A 0.9300 . ?
C32 C33 1.391(7) . ?
C32 C31 1.398(7) . ?
C32 C37 1.522(7) . ?
C36 C31 1.398(6) . ?
C36 C35 1.404(7) . ?
C36 C40 1.505(7) . ?
C11 C12 1.389(7) . ?
C11 C16 1.409(7) . ?
C1 C2 1.515(7) . ?
C12 C13 1.399(7) . ?
C12 C17 1.523(7) . ?
C56 C51 1.368(7) . ?
C56 C55 1.387(7) . ?
C56 H56A 0.9300 . ?
C4 H4A 0.9300 . ?
C14 C13 1.374(7) . ?
C14 C15 1.378(7) . ?
C14 H14A 0.9300 . ?
C16 C15 1.404(7) . ?
C16 C20 1.501(7) . ?
C2 C51 1.472(7) . ?
C42 C40 1.536(7) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C15 H15A 0.9300 . ?
C35 C34 1.361(7) . ?
C35 H35A 0.9300 . ?
C34 C33 1.382(7) . ?
C34 H34A 0.9300 . ?
C20 C22 1.533(7) . ?
C20 C21 1.534(7) . ?
C20 H20A 0.9800 . ?
C51 C52 1.397(7) . ?
C55 C54 1.352(9) . ?
C55 H55A 0.9300 . ?
C33 H33A 0.9300 . ?
C37 C39 1.521(7) . ?
C37 C38 1.527(7) . ?
C37 H37A 0.9800 . ?
C40 C41 1.528(7) . ?
C40 H40A 0.9800 . ?
C17 C18 1.516(7) . ?
C17 C19 1.525(7) . ?
C17 H17A 0.9800 . ?
C13 H13A 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C52 C53 1.379(8) . ?
C52 H52A 0.9300 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C53 C54 1.369(9) . ?
C53 H53A 0.9300 . ?
C54 H54A 0.9300 . ?

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
C1 N2 C3 108.1(4) . . ?
C1 N2 C31 124.7(4) . . ?
C3 N2 C31 125.6(4) . . ?
C1 N1 C4 108.6(4) . . ?
C1 N1 C11 127.2(4) . . ?
C4 N1 C11 124.1(4) . . ?
C4 C3 N2 107.6(4) . . ?
C4 C3 H3A 126.2 . . ?
N2 C3 H3A 126.2 . . ?
C33 C32 C31 116.3(5) . . ?
C33 C32 C37 119.2(5) . . ?
C31 C32 C37 124.4(5) . . ?
C31 C36 C35 115.1(5) . . ?
C31 C36 C40 124.2(5) . . ?
C35 C36 C40 120.4(5) . . ?
C12 C11 C16 124.3(5) . . ?
C12 C11 N1 117.9(5) . . ?
C16 C11 N1 117.8(5) . . ?
C36 C31 C32 124.6(5) . . ?
C36 C31 N2 118.7(5) . . ?
C32 C31 N2 116.8(4) . . ?
N1 C1 N2 108.7(4) . . ?
N1 C1 C2 125.8(5) . . ?
N2 C1 C2 125.1(5) . . ?
C11 C12 C13 116.0(5) . . ?
C11 C12 C17 123.9(5) . . ?
C13 C12 C17 120.1(5) . . ?
C51 C56 C55 120.4(6) . . ?
C51 C56 H56A 119.8 . . ?
C55 C56 H56A 119.8 . . ?
C3 C4 N1 107.0(5) . . ?
C3 C4 H4A 126.5 . . ?
N1 C4 H4A 126.5 . . ?
C13 C14 C15 120.4(6) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
C15 C16 C11 116.2(5) . . ?
C15 C16 C20 120.2(5) . . ?
C11 C16 C20 123.5(5) . . ?
O3 C2 C51 122.2(5) . . ?
O3 C2 C1 117.4(5) . . ?
C51 C2 C1 120.4(5) . . ?
C40 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C40 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C14 C15 C16 121.0(5) . . ?
C14 C15 H15A 119.5 . . ?
C16 C15 H15A 119.5 . . ?
C34 C35 C36 122.3(5) . . ?
C34 C35 H35A 118.8 . . ?
C36 C35 H35A 118.8 . . ?
C35 C34 C33 120.3(5) . . ?
C35 C34 H34A 119.8 . . ?
C33 C34 H34A 119.8 . . ?
C16 C20 C22 110.0(5) . . ?
C16 C20 C21 112.7(5) . . ?
C22 C20 C21 110.1(5) . . ?
C16 C20 H20A 108.0 . . ?
C22 C20 H20A 108.0 . . ?
C21 C20 H20A 108.0 . . ?
C56 C51 C52 118.9(6) . . ?
C56 C51 C2 122.7(5) . . ?
C52 C51 C2 118.2(5) . . ?
C54 C55 C56 119.9(7) . . ?
C54 C55 H55A 120.0 . . ?
C56 C55 H55A 120.0 . . ?
C34 C33 C32 121.3(6) . . ?
C34 C33 H33A 119.4 . . ?
C32 C33 H33A 119.4 . . ?
C39 C37 C32 111.9(5) . . ?
C39 C37 C38 112.2(5) . . ?
C32 C37 C38 110.7(5) . . ?
C39 C37 H37A 107.2 . . ?
C32 C37 H37A 107.2 . . ?
C38 C37 H37A 107.2 . . ?
C36 C40 C41 110.3(4) . . ?
C36 C40 C42 113.4(5) . . ?
C41 C40 C42 110.1(4) . . ?
C36 C40 H40A 107.6 . . ?
C41 C40 H40A 107.6 . . ?
C42 C40 H40A 107.6 . . ?
C18 C17 C12 111.9(5) . . ?
C18 C17 C19 111.2(5) . . ?
C12 C17 C19 110.7(5) . . ?
C18 C17 H17A 107.6 . . ?
C12 C17 H17A 107.6 . . ?
C19 C17 H17A 107.6 . . ?
C14 C13 C12 122.0(6) . . ?
C14 C13 H13A 119.0 . . ?
C12 C13 H13A 119.0 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
Cl2 C30 Cl3 110.9(3) . . ?
Cl2 C30 H30A 109.5 . . ?
Cl3 C30 H30A 109.5 . . ?
Cl2 C30 H30B 109.5 . . ?
Cl3 C30 H30B 109.5 . . ?
H30A C30 H30B 108.0 . . ?
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 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C53 C52 C51 120.2(7) . . ?
C53 C52 H52A 119.9 . . ?
C51 C52 H52A 119.9 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 . . ?
C54 C53 C52 119.5(7) . . ?
C54 C53 H53A 120.3 . . ?
C52 C53 H53A 120.3 . . ?
C55 C54 C53 121.1(7) . . ?
C55 C54 H54A 119.5 . . ?
C53 C54 H54A 119.5 . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.062



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexanes and dichloromethane'
_chemical_properties_physical    Hygroscopic
####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1025145'
_audit_update_record             
;
2014-09-18 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'DAC-COPh Radical'
_chemical_melting_point          ?
_chemical_formula_moiety         {(C24H28N2O2)-(COC6H5)}
_chemical_formula_sum            'C31 H33 N2 O3'
_chemical_formula_weight         481.59

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'
O O 0.0106 0.0060 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.8892(10)
_cell_length_b                   16.2557(14)
_cell_length_c                   13.7767(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.327(7)
_cell_angle_gamma                90
_cell_volume                     2646.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_F_000             1028
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.078
_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   none
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22167
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.042
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4656
_reflns_number_gt                3277
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0086P)²+2.2590P] 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         4656
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.001

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
O1 O 0.98247(14) -0.01803(9) 0.28080(13) 0.0532(5) Uani 1 1 d . . . . .
N1 N 0.99732(14) 0.11321(10) 0.22912(13) 0.0336(4) Uani 1 1 d . . . . .
C1 C 0.94414(17) 0.19218(12) 0.21337(15) 0.0308(5) Uani 1 1 d . . . . .
O2 O 0.66840(13) 0.13252(10) 0.26726(12) 0.0516(4) Uani 1 1 d . . . . .
N2 N 0.82244(14) 0.18826(10) 0.20816(12) 0.0329(4) Uani 1 1 d . . . . .
C2 C 1.00395(18) 0.26072(13) 0.20056(16) 0.0351(5) Uani 1 1 d . . . . .
O3 O 0.94928(13) 0.32984(9) 0.16335(13) 0.0539(5) Uani 1 1 d . . . . .
C3 C 0.94782(18) 0.05316(13) 0.27932(17) 0.0380(5) Uani 1 1 d . . . . .
C4 C 0.85007(19) 0.08076(14) 0.33423(16) 0.0395(5) Uani 1 1 d . . . . .
C5 C 0.77091(19) 0.13544(13) 0.26797(16) 0.0369(5) Uani 1 1 d . . . . .
C6 C 0.7855(2) 0.00591(16) 0.3659(2) 0.0620(8) Uani 1 1 d . . . . .
H6A H 0.7541 -0.0240 0.3092 0.093 Uiso 1 1 calc R U . . .
H6B H 0.7255 0.0238 0.4022 0.093 Uiso 1 1 calc R U . . .
H6C H 0.8362 -0.0291 0.4062 0.093 Uiso 1 1 calc R U . . .
C7 C 0.8962(2) 0.13186(17) 0.42466(17) 0.0559(7) Uani 1 1 d . . . . .
H7A H 0.9364 0.1789 0.4041 0.084 Uiso 1 1 calc R U . . .
H7B H 0.9467 0.0986 0.4674 0.084 Uiso 1 1 calc R U . . .
H7C H 0.8344 0.1499 0.4586 0.084 Uiso 1 1 calc R U . . .
C11 C 1.10464(18) 0.09536(12) 0.19131(16) 0.0347(5) Uani 1 1 d . . . . .
C12 C 1.19985(19) 0.08103(13) 0.25809(17) 0.0402(6) Uani 1 1 d . . . . .
C13 C 1.30382(19) 0.07234(14) 0.2213(2) 0.0473(6) Uani 1 1 d . . . . .
H13A H 1.3683 0.0640 0.2649 0.057 Uiso 1 1 calc R U . . .
C14 C 1.3149(2) 0.07562(14) 0.1227(2) 0.0481(6) Uani 1 1 d . . . . .
C15 C 1.2174(2) 0.08477(14) 0.05868(19) 0.0474(6) Uani 1 1 d . . . . .
H15A H 1.2230 0.0839 -0.0081 0.057 Uiso 1 1 calc R U . . .
C16 C 1.11107(18) 0.09524(13) 0.09085(17) 0.0392(5) Uani 1 1 d . . . . .
C17 C 1.1943(2) 0.07483(17) 0.36644(18) 0.0558(7) Uani 1 1 d . . . . .
H17A H 1.2670 0.0877 0.4004 0.084 Uiso 1 1 calc R U . . .
H17B H 1.1733 0.0199 0.3826 0.084 Uiso 1 1 calc R U . . .
H17C H 1.1390 0.1129 0.3854 0.084 Uiso 1 1 calc R U . . .
C18 C 1.4309(2) 0.07165(18) 0.0868(2) 0.0722(9) Uani 1 1 d . . . . .
H18A H 1.4226 0.0672 0.0169 0.108 Uiso 1 1 calc R U . . .
H18B H 1.4710 0.0245 0.1147 0.108 Uiso 1 1 calc R U . . .
H18C H 1.4725 0.1207 0.1061 0.108 Uiso 1 1 calc R U . . .
C19 C 1.0086(2) 0.10772(16) 0.01793(18) 0.0527(7) Uani 1 1 d . . . . .
H19A H 1.0278 0.0961 -0.0465 0.079 Uiso 1 1 calc R U . . .
H19B H 0.9834 0.1637 0.0209 0.079 Uiso 1 1 calc R U . . .
H19C H 0.9493 0.0714 0.0329 0.079 Uiso 1 1 calc R U . . .
C21 C 0.74528(17) 0.23920(13) 0.14410(15) 0.0327(5) Uani 1 1 d . . . . .
C22 C 0.71093(19) 0.31548(14) 0.17653(16) 0.0393(5) Uani 1 1 d . . . . .
C23 C 0.63399(19) 0.36068(14) 0.11434(18) 0.0466(6) Uani 1 1 d . . . . .
H23A H 0.6116 0.4122 0.1343 0.056 Uiso 1 1 calc R U . . .
C24 C 0.58970(19) 0.33131(15) 0.02374(18) 0.0457(6) Uani 1 1 d . . . . .
C25 C 0.62032(18) 0.25341(15) -0.00289(17) 0.0445(6) Uani 1 1 d . . . . .
H25A H 0.5892 0.2323 -0.0626 0.053 Uiso 1 1 calc R U . . .
C26 C 0.69636(17) 0.20518(13) 0.05667(16) 0.0362(5) Uani 1 1 d . . . . .
C27 C 0.7502(2) 0.34731(16) 0.27725(18) 0.0595(7) Uani 1 1 d . . . . .
H27A H 0.6901 0.3776 0.3018 0.089 Uiso 1 1 calc R U . . .
H27B H 0.8143 0.3828 0.2742 0.089 Uiso 1 1 calc R U . . .
H27C H 0.7714 0.3019 0.3199 0.089 Uiso 1 1 calc R U . . .
C28 C 0.5068(2) 0.38184(18) -0.0430(2) 0.0668(8) Uani 1 1 d . . . . .
H28A H 0.4518 0.3461 -0.0774 0.100 Uiso 1 1 calc R U . . .
H28B H 0.5468 0.4111 -0.0890 0.100 Uiso 1 1 calc R U . . .
H28C H 0.4691 0.4204 -0.0048 0.100 Uiso 1 1 calc R U . . .
C29 C 0.7163(2) 0.11742(14) 0.02795(18) 0.0478(6) Uani 1 1 d . . . . .
H29A H 0.6467 0.0941 -0.0018 0.072 Uiso 1 1 calc R U . . .
H29B H 0.7431 0.0862 0.0850 0.072 Uiso 1 1 calc R U . . .
H29C H 0.7718 0.1161 -0.0177 0.072 Uiso 1 1 calc R U . . .
C31 C 1.12938(18) 0.27066(12) 0.21877(17) 0.0376(5) Uani 1 1 d . . . . .
C32 C 1.1810(2) 0.27734(15) 0.31366(19) 0.0499(6) Uani 1 1 d . . . . .
H32A H 1.1378 0.2725 0.3657 0.060 Uiso 1 1 calc R U . . .
C33 C 1.2969(2) 0.29125(17) 0.3316(2) 0.0678(8) Uani 1 1 d . . . . .
H33A H 1.3309 0.2956 0.3955 0.081 Uiso 1 1 calc R U . . .
C34 C 1.3614(2) 0.29850(18) 0.2552(3) 0.0753(10) Uani 1 1 d . . . . .
H34A H 1.4391 0.3065 0.2675 0.090 Uiso 1 1 calc R U . . .
C35 C 1.3113(2) 0.29393(16) 0.1611(3) 0.0672(8) Uani 1 1 d . . . . .
H35A H 1.3551 0.2993 0.1095 0.081 Uiso 1 1 calc R U . . .
C36 C 1.1951(2) 0.28129(14) 0.1420(2) 0.0505(6) Uani 1 1 d . . . . .
H36A H 1.1614 0.2799 0.0779 0.061 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
O1 C3 1.228(2) . ?
N1 C3 1.366(3) . ?
N1 C1 1.437(2) . ?
N1 C11 1.460(3) . ?
C1 C2 1.344(3) . ?
C1 N2 1.442(3) . ?
O2 C5 1.219(2) . ?
N2 C5 1.379(3) . ?
N2 C21 1.459(3) . ?
C2 O3 1.369(2) . ?
C2 C31 1.493(3) . ?
C3 C4 1.522(3) . ?
C4 C5 1.523(3) . ?
C4 C6 1.528(3) . ?
C4 C7 1.547(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C11 C16 1.394(3) . ?
C11 C12 1.397(3) . ?
C12 C13 1.394(3) . ?
C12 C17 1.505(3) . ?
C13 C14 1.380(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.385(3) . ?
C14 C18 1.517(3) . ?
C15 C16 1.395(3) . ?
C15 H15A 0.9300 . ?
C16 C19 1.505(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 C26 1.393(3) . ?
C21 C22 1.394(3) . ?
C22 C23 1.392(3) . ?
C22 C27 1.506(3) . ?
C23 C24 1.385(3) . ?
C23 H23A 0.9300 . ?
C24 C25 1.378(3) . ?
C24 C28 1.514(3) . ?
C25 C26 1.393(3) . ?
C25 H25A 0.9300 . ?
C26 C29 1.506(3) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C31 C32 1.386(3) . ?
C31 C36 1.393(3) . ?
C32 C33 1.392(3) . ?
C32 H32A 0.9300 . ?
C33 C34 1.373(4) . ?
C33 H33A 0.9300 . ?
C34 C35 1.368(4) . ?
C34 H34A 0.9300 . ?
C35 C36 1.392(4) . ?
C35 H35A 0.9300 . ?
C36 H36A 0.9300 . ?

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
C3 N1 C1 120.52(17) . . ?
C3 N1 C11 118.74(17) . . ?
C1 N1 C11 120.74(16) . . ?
C2 C1 N1 122.02(18) . . ?
C2 C1 N2 124.93(18) . . ?
N1 C1 N2 112.98(17) . . ?
C5 N2 C1 120.46(17) . . ?
C5 N2 C21 115.07(17) . . ?
C1 N2 C21 124.45(16) . . ?
C1 C2 O3 119.56(19) . . ?
C1 C2 C31 126.92(19) . . ?
O3 C2 C31 113.46(18) . . ?
O1 C3 N1 121.3(2) . . ?
O1 C3 C4 122.9(2) . . ?
N1 C3 C4 115.84(18) . . ?
C5 C4 C3 109.22(18) . . ?
C5 C4 C6 109.82(19) . . ?
C3 C4 C6 110.02(19) . . ?
C5 C4 C7 108.07(19) . . ?
C3 C4 C7 109.62(19) . . ?
C6 C4 C7 110.0(2) . . ?
O2 C5 N2 121.9(2) . . ?
O2 C5 C4 122.2(2) . . ?
N2 C5 C4 115.82(18) . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C16 C11 C12 121.6(2) . . ?
C16 C11 N1 120.01(19) . . ?
C12 C11 N1 118.3(2) . . ?
C13 C12 C11 117.6(2) . . ?
C13 C12 C17 119.5(2) . . ?
C11 C12 C17 122.9(2) . . ?
C14 C13 C12 122.6(2) . . ?
C14 C13 H13A 118.7 . . ?
C12 C13 H13A 118.7 . . ?
C13 C14 C15 117.9(2) . . ?
C13 C14 C18 120.5(2) . . ?
C15 C14 C18 121.6(3) . . ?
C14 C15 C16 122.3(2) . . ?
C14 C15 H15A 118.8 . . ?
C16 C15 H15A 118.8 . . ?
C11 C16 C15 117.8(2) . . ?
C11 C16 C19 122.2(2) . . ?
C15 C16 C19 120.0(2) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 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 . . ?
C26 C21 C22 121.4(2) . . ?
C26 C21 N2 118.21(18) . . ?
C22 C21 N2 119.86(19) . . ?
C23 C22 C21 117.9(2) . . ?
C23 C22 C27 120.1(2) . . ?
C21 C22 C27 121.9(2) . . ?
C24 C23 C22 122.1(2) . . ?
C24 C23 H23A 118.9 . . ?
C22 C23 H23A 118.9 . . ?
C25 C24 C23 118.1(2) . . ?
C25 C24 C28 120.7(2) . . ?
C23 C24 C28 121.2(2) . . ?
C24 C25 C26 122.2(2) . . ?
C24 C25 H25A 118.9 . . ?
C26 C25 H25A 118.9 . . ?
C21 C26 C25 117.9(2) . . ?
C21 C26 C29 122.7(2) . . ?
C25 C26 C29 119.3(2) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C32 C31 C36 118.6(2) . . ?
C32 C31 C2 119.8(2) . . ?
C36 C31 C2 121.3(2) . . ?
C31 C32 C33 120.5(3) . . ?
C31 C32 H32A 119.8 . . ?
C33 C32 H32A 119.8 . . ?
C34 C33 C32 120.2(3) . . ?
C34 C33 H33A 119.9 . . ?
C32 C33 H33A 119.9 . . ?
C35 C34 C33 120.0(3) . . ?
C35 C34 H34A 120.0 . . ?
C33 C34 H34A 120.0 . . ?
C34 C35 C36 120.4(3) . . ?
C34 C35 H35A 119.8 . . ?
C36 C35 H35A 119.8 . . ?
C35 C36 C31 120.2(3) . . ?
C35 C36 H36A 119.9 . . ?
C31 C36 H36A 119.9 . . ?

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.036



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: cold hexanes'
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
