# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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data_20170512cz_xgh_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1577296'
_audit_update_record             
;
2017-09-29 deposited with the CCDC.
2017-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H26 N2 O2'
_chemical_formula_weight         398.49

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      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                   9.5772(10)
_cell_length_b                   10.5178(11)
_cell_length_c                   11.9976(11)
_cell_angle_alpha                89.889(3)
_cell_angle_beta                 67.004(2)
_cell_angle_gamma                70.688(3)
_cell_volume                     1038.57(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5943
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.56
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            7352
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.405
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_full        25.007
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3604
_reflns_number_gt                3232
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0540P)²+0.3360P] 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         3604
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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 0.77964(17) -0.02382(14) 0.22204(12) 0.0236(3) Uani 1 1 d . . . . .
H1 H 0.815587 0.047607 0.225012 0.028 Uiso 1 1 calc R U . . .
C2 C 0.89148(18) -0.15240(15) 0.16512(13) 0.0272(3) Uani 1 1 d . . . . .
H2 H 1.002003 -0.167240 0.130118 0.033 Uiso 1 1 calc R U . . .
C3 C 0.83801(19) -0.25917(15) 0.16049(13) 0.0292(3) Uani 1 1 d . . . . .
H3 H 0.912747 -0.345701 0.122346 0.035 Uiso 1 1 calc R U . . .
C4 C 0.67309(18) -0.23665(14) 0.21279(13) 0.0270(3) Uani 1 1 d . . . . .
H4 H 0.638226 -0.308656 0.209345 0.032 Uiso 1 1 calc R U . . .
C5 C 0.55918(17) -0.10840(14) 0.27019(12) 0.0220(3) Uani 1 1 d . . . . .
C6 C 0.61278(16) -0.00023(13) 0.27522(11) 0.0200(3) Uani 1 1 d . . . . .
C7 C 0.49102(16) 0.13392(13) 0.34280(12) 0.0187(3) Uani 1 1 d . . . . .
C8 C 0.33999(16) 0.14711(13) 0.42137(12) 0.0193(3) Uani 1 1 d . . . . .
C9 C 0.29133(17) 0.02345(13) 0.44283(12) 0.0228(3) Uani 1 1 d . . . . .
H9A H 0.174855 0.051092 0.468569 0.027 Uiso 1 1 calc R U . . .
H9B H 0.317596 -0.017762 0.507910 0.027 Uiso 1 1 calc R U . . .
C10 C 0.37867(17) -0.08077(14) 0.32712(13) 0.0242(3) Uani 1 1 d . . . . .
H10A H 0.360732 -0.165105 0.346911 0.029 Uiso 1 1 calc R U . . .
H10B H 0.333637 -0.047298 0.268466 0.029 Uiso 1 1 calc R U . . .
C11 C 0.21852(16) 0.27812(13) 0.50091(12) 0.0200(3) Uani 1 1 d . . . . .
H11A H 0.117245 0.297794 0.492200 0.024 Uiso 1 1 calc R U . . .
H11B H 0.197374 0.268422 0.585802 0.024 Uiso 1 1 calc R U . . .
C12 C 0.44996(15) 0.34642(13) 0.44282(11) 0.0188(3) Uani 1 1 d . . . . .
H12A H 0.484879 0.423999 0.430662 0.023 Uiso 1 1 calc R U . . .
H12B H 0.466966 0.308583 0.512267 0.023 Uiso 1 1 calc R U . . .
C13 C 0.59557(15) 0.29336(12) 0.21938(11) 0.0175(3) Uani 1 1 d . . . . .
C14 C 0.69226(15) 0.37323(13) 0.19573(12) 0.0190(3) Uani 1 1 d . . . . .
H14 H 0.722284 0.395769 0.255750 0.023 Uiso 1 1 calc R U . . .
C15 C 0.74374(15) 0.41909(13) 0.08401(12) 0.0200(3) Uani 1 1 d . . . . .
H15 H 0.807118 0.472964 0.069844 0.024 Uiso 1 1 calc R U . . .
C16 C 0.70140(15) 0.38519(13) -0.00771(11) 0.0190(3) Uani 1 1 d . . . . .
C17 C 0.60752(16) 0.30436(14) 0.01395(12) 0.0218(3) Uani 1 1 d . . . . .
H17 H 0.580066 0.279889 -0.046953 0.026 Uiso 1 1 calc R U . . .
C18 C 0.55438(16) 0.25986(13) 0.12738(12) 0.0211(3) Uani 1 1 d . . . . .
H18 H 0.490133 0.206721 0.141761 0.025 Uiso 1 1 calc R U . . .
C19 C 0.72272(18) 0.39977(16) -0.21191(12) 0.0271(3) Uani 1 1 d . . . . .
H19A H 0.775888 0.303533 -0.239355 0.041 Uiso 1 1 calc R U . . .
H19B H 0.759823 0.448116 -0.278650 0.041 Uiso 1 1 calc R U . . .
H19C H 0.607363 0.423472 -0.182891 0.041 Uiso 1 1 calc R U . . .
C20 C 0.17871(15) 0.51700(13) 0.55012(11) 0.0181(3) Uani 1 1 d . . . . .
C21 C 0.04673(16) 0.53070(14) 0.66058(12) 0.0210(3) Uani 1 1 d . . . . .
H21 H 0.020082 0.454530 0.684128 0.025 Uiso 1 1 calc R U . . .
C22 C -0.04613(16) 0.65516(14) 0.73648(12) 0.0232(3) Uani 1 1 d . . . . .
H22 H -0.134354 0.661726 0.809150 0.028 Uiso 1 1 calc R U . . .
C23 C -0.00683(16) 0.76932(13) 0.70351(12) 0.0213(3) Uani 1 1 d . . . . .
C24 C 0.12318(16) 0.75823(13) 0.59235(12) 0.0216(3) Uani 1 1 d . . . . .
H24 H 0.149134 0.834722 0.568919 0.026 Uiso 1 1 calc R U . . .
C25 C 0.21332(16) 0.63492(14) 0.51710(12) 0.0202(3) Uani 1 1 d . . . . .
H25 H 0.298758 0.629648 0.442990 0.024 Uiso 1 1 calc R U . . .
C26 C -0.1999(2) 0.90573(17) 0.89480(14) 0.0423(4) Uani 1 1 d . . . . .
H26A H -0.291111 0.887606 0.893395 0.063 Uiso 1 1 calc R U . . .
H26B H -0.236360 0.995685 0.937333 0.063 Uiso 1 1 calc R U . . .
H26C H -0.148982 0.840276 0.936047 0.063 Uiso 1 1 calc R U . . .
N1 N 0.27551(13) 0.39193(11) 0.46931(10) 0.0186(3) Uani 1 1 d . . . . .
N2 N 0.54659(13) 0.24477(11) 0.33469(9) 0.0184(3) Uani 1 1 d . . . . .
O1 O -0.08585(12) 0.89624(10) 0.77250(9) 0.0282(3) Uani 1 1 d . . . . .
O2 O 0.76003(11) 0.43573(10) -0.11502(8) 0.0241(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.384(2) . ?
C1 C6 1.401(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3883(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.4044(19) . ?
C5 C10 1.5118(19) . ?
C6 C7 1.4783(18) . ?
C7 C8 1.3426(19) . ?
C7 N2 1.4218(17) . ?
C8 C11 1.4967(18) . ?
C8 C9 1.5103(18) . ?
C9 C10 1.5233(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N1 1.4640(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.4475(16) . ?
C12 N1 1.4759(16) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.3899(18) . ?
C13 C14 1.3972(18) . ?
C13 N2 1.4297(16) . ?
C14 C15 1.3823(18) . ?
C14 H14 0.9300 . ?
C15 C16 1.3958(19) . ?
C15 H15 0.9300 . ?
C16 O2 1.3731(15) . ?
C16 C17 1.3860(19) . ?
C17 C18 1.3943(19) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O2 1.4275(16) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.3950(18) . ?
C20 C25 1.4045(19) . ?
C20 N1 1.4233(16) . ?
C21 C22 1.3912(19) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(2) . ?
C22 H22 0.9300 . ?
C23 O1 1.3735(16) . ?
C23 C24 1.3963(19) . ?
C24 C25 1.3774(19) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 O1 1.4256(19) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
C2 C1 C6 120.65(13) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C1 C2 C3 119.76(13) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 119.96(13) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.09(13) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 119.12(13) . . ?
C4 C5 C10 122.19(12) . . ?
C6 C5 C10 118.68(12) . . ?
C1 C6 C5 119.43(12) . . ?
C1 C6 C7 121.90(12) . . ?
C5 C6 C7 118.58(12) . . ?
C8 C7 N2 120.89(12) . . ?
C8 C7 C6 121.38(12) . . ?
N2 C7 C6 117.13(11) . . ?
C7 C8 C11 123.05(12) . . ?
C7 C8 C9 120.13(12) . . ?
C11 C8 C9 116.51(11) . . ?
C8 C9 C10 111.08(11) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C5 C10 C9 111.59(11) . . ?
C5 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C5 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
N1 C11 C8 111.92(10) . . ?
N1 C11 H11A 109.2 . . ?
C8 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C8 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N2 C12 N1 111.22(10) . . ?
N2 C12 H12A 109.4 . . ?
N1 C12 H12A 109.4 . . ?
N2 C12 H12B 109.4 . . ?
N1 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C18 C13 C14 118.37(12) . . ?
C18 C13 N2 121.95(11) . . ?
C14 C13 N2 119.65(11) . . ?
C15 C14 C13 120.66(12) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.55(12) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
O2 C16 C17 125.15(12) . . ?
O2 C16 C15 115.48(11) . . ?
C17 C16 C15 119.37(12) . . ?
C16 C17 C18 119.76(12) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C13 C18 C17 121.29(12) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 117.27(12) . . ?
C21 C20 N1 123.54(12) . . ?
C25 C20 N1 119.17(11) . . ?
C22 C21 C20 121.83(12) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C23 C22 C21 119.83(12) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
O1 C23 C22 125.15(12) . . ?
O1 C23 C24 115.64(12) . . ?
C22 C23 C24 119.21(12) . . ?
C25 C24 C23 120.55(12) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C20 121.28(12) . . ?
C24 C25 H25 119.4 . . ?
C20 C25 H25 119.4 . . ?
O1 C26 H26A 109.5 . . ?
O1 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O1 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C20 N1 C11 116.10(10) . . ?
C20 N1 C12 114.38(10) . . ?
C11 N1 C12 109.43(10) . . ?
C7 N2 C13 117.61(10) . . ?
C7 N2 C12 111.87(10) . . ?
C13 N2 C12 116.91(10) . . ?
C23 O1 C26 116.84(11) . . ?
C16 O2 C19 116.89(10) . . ?

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.044

