# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_twin5
_database_code_depnum_ccdc_archive 'CCDC 1583863'
_audit_update_record             
;
2017-11-03 deposited with the CCDC.
2018-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H34 N6 O6'
_chemical_formula_weight         646.69

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                   11.001(4)
_cell_length_b                   24.698(10)
_cell_length_c                   6.161(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.192(12)
_cell_angle_gamma                90
_cell_volume                     1672.7(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    894
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      24.70

_exptl_crystal_description       Plate
_exptl_crystal_colour            Purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3829
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3280
_diffrn_reflns_av_unetI/netI     0.1695
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.853
_diffrn_reflns_theta_max         26.026
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3280
_reflns_number_gt                1545
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1143P)²+1.8772P] 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         3280
_refine_ls_number_parameters     223
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.2159
_refine_ls_R_factor_gt           0.1013
_refine_ls_wR_factor_ref         0.3024
_refine_ls_wR_factor_gt          0.2322
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.3799(4) 0.62555(16) 0.8651(6) 0.0410(11) Uani 1 1 d . . . . .
H1A H 0.404(7) 0.604(3) 0.987(13) 0.09(3) Uiso 1 1 d . . . . .
O2 O 0.3647(4) 0.68367(16) 0.5125(6) 0.0429(11) Uani 1 1 d . . . . .
N1 N 0.5032(4) 0.56344(18) 1.1232(6) 0.0322(12) Uani 1 1 d . . . . .
N2 N 0.7938(4) 0.64264(19) 0.3861(7) 0.0376(12) Uani 1 1 d . . . . .
N3 N 0.7886(4) 0.67195(19) 0.2191(7) 0.0381(13) Uani 1 1 d . . . . .
C1 C 0.3967(6) 0.5003(2) 1.6202(9) 0.0386(15) Uani 1 1 d . . . . .
H1 H 0.3252 0.5009 1.7019 0.046 Uiso 1 1 calc R U . . .
C2 C 0.4027(5) 0.5310(2) 1.4336(8) 0.0339(14) Uani 1 1 d . . . . .
H2 H 0.3348 0.5524 1.3875 0.041 Uiso 1 1 calc R U . . .
C3 C 0.5063(5) 0.5310(2) 1.3124(8) 0.0309(14) Uani 1 1 d . . . . .
C4 C 0.5976(6) 0.5721(2) 1.0095(8) 0.0336(14) Uani 1 1 d . . . . .
H4 H 0.6736 0.5566 1.0539 0.040 Uiso 1 1 calc R U . . .
C5 C 0.5891(5) 0.6049(2) 0.8168(8) 0.0323(14) Uani 1 1 d . . . . .
C6 C 0.4809(5) 0.6307(2) 0.7512(8) 0.0310(14) Uani 1 1 d . . . . .
C7 C 0.4756(6) 0.6620(2) 0.5613(8) 0.0314(14) Uani 1 1 d . . . . .
C8 C 0.5767(5) 0.6678(2) 0.4404(8) 0.0313(14) Uani 1 1 d . . . . .
H8 H 0.5733 0.6896 0.3134 0.038 Uiso 1 1 calc R U . . .
C9 C 0.6854(5) 0.6415(2) 0.5043(8) 0.0318(13) Uani 1 1 d . . . . .
C10 C 0.6915(5) 0.6106(2) 0.6900(8) 0.0351(14) Uani 1 1 d . . . . .
H10 H 0.7655 0.5930 0.7327 0.042 Uiso 1 1 calc R U . . .
C11 C 0.3551(6) 0.7183(3) 0.3295(9) 0.0483(17) Uani 1 1 d . . . . .
H11A H 0.4177 0.7464 0.3423 0.073 Uiso 1 1 calc R U . . .
H11B H 0.2744 0.7352 0.3223 0.073 Uiso 1 1 calc R U . . .
H11C H 0.3665 0.6971 0.1971 0.073 Uiso 1 1 calc R U . . .
C12 C 0.8994(6) 0.6712(2) 0.1041(9) 0.0358(14) Uani 1 1 d . . . . .
C13 C 0.8948(6) 0.6974(2) -0.0943(9) 0.0388(15) Uani 1 1 d . . . . .
H13 H 0.8227 0.7155 -0.1432 0.047 Uiso 1 1 calc R U . . .
C14 C 0.9960(6) 0.6970(3) -0.2216(10) 0.0437(16) Uani 1 1 d . . . . .
H14 H 0.9927 0.7143 -0.3595 0.052 Uiso 1 1 calc R U . . .
C15 C 1.1012(7) 0.6717(3) -0.1493(10) 0.0499(18) Uani 1 1 d . . . . .
H15 H 1.1705 0.6714 -0.2366 0.060 Uiso 1 1 calc R U . . .
C16 C 1.1051(6) 0.6470(3) 0.0512(11) 0.0539(18) Uani 1 1 d . . . . .
H16 H 1.1783 0.6300 0.1021 0.065 Uiso 1 1 calc R U . . .
C17 C 1.0057(6) 0.6463(3) 0.1788(10) 0.0486(18) Uani 1 1 d . . . . .
H17 H 1.0096 0.6290 0.3165 0.058 Uiso 1 1 calc R U . . .
C100 C 1.064(3) 0.4959(14) 0.021(9) 0.329(17) Uani 1 1 d . U . . .
O100 O 0.998(2) 0.4989(5) 0.285(4) 0.318(9) Uani 1 1 d . 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 C6 1.343(6) . ?
O1 H1A 0.96(8) . ?
O2 C7 1.355(7) . ?
O2 C11 1.415(6) . ?
N1 C4 1.293(7) . ?
N1 C3 1.414(7) . ?
N2 N3 1.257(6) . ?
N2 C9 1.421(7) . ?
N3 C12 1.433(7) . ?
C1 C3 1.369(8) 3_668 ?
C1 C2 1.380(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(8) . ?
C2 H2 0.9500 . ?
C3 C1 1.369(8) 3_668 ?
C4 C5 1.437(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(8) . ?
C5 C10 1.402(8) . ?
C6 C7 1.400(7) . ?
C7 C8 1.370(8) . ?
C8 C9 1.404(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.375(7) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.382(8) . ?
C12 C17 1.384(9) . ?
C13 C14 1.386(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.372(9) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C100 C100 1.43(6) 3_765 ?
C100 O100 1.81(5) . ?

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
C6 O1 H1A 105(5) . . ?
C7 O2 C11 117.1(5) . . ?
C4 N1 C3 123.0(5) . . ?
N3 N2 C9 114.7(5) . . ?
N2 N3 C12 112.6(5) . . ?
C3 C1 C2 120.1(6) 3_668 . ?
C3 C1 H1 120.0 3_668 . ?
C2 C1 H1 120.0 . . ?
C1 C2 C3 121.0(6) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C1 C3 C2 118.9(5) 3_668 . ?
C1 C3 N1 124.4(5) 3_668 . ?
C2 C3 N1 116.7(5) . . ?
N1 C4 C5 120.8(6) . . ?
N1 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C10 119.1(5) . . ?
C6 C5 C4 121.7(5) . . ?
C10 C5 C4 119.2(6) . . ?
O1 C6 C5 121.2(5) . . ?
O1 C6 C7 118.6(5) . . ?
C5 C6 C7 120.1(5) . . ?
O2 C7 C8 125.5(5) . . ?
O2 C7 C6 114.3(5) . . ?
C8 C7 C6 120.2(6) . . ?
C7 C8 C9 120.0(5) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 120.3(5) . . ?
C10 C9 N2 115.0(5) . . ?
C8 C9 N2 124.7(5) . . ?
C9 C10 C5 120.3(6) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 120.2(6) . . ?
C13 C12 N3 115.4(6) . . ?
C17 C12 N3 124.4(5) . . ?
C12 C13 C14 119.6(6) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 120.3(6) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.3(6) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 121.4(7) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C12 119.1(6) . . ?
C16 C17 H17 120.5 . . ?
C12 C17 H17 120.5 . . ?
C100 C100 O100 74(4) 3_765 . ?

_refine_diff_density_max         0.729
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.095

_shelxl_version_number           2013-4

