# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ao1088
_database_code_depnum_ccdc_archive 'CCDC 1838265'
_audit_update_record             
;
2018-04-19 deposited with the CCDC.
2018-08-01 downloaded from the CCDC.
;

_audit_creation_date             2016-11-10T11:35:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C42.50 H29 N3 O0.50'
_chemical_formula_moiety         'C42 H27 N3, 0.50(C H4 O)'
_chemical_formula_weight         589.69

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'R -3 :H'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_Int_Tables_number      148
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   21.9820(5)
_cell_length_b                   21.9820(5)
_cell_length_c                   10.3781(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4342.9(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1448
_cell_measurement_theta_min      4.841
_cell_measurement_theta_max      67.158

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.146
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.042
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             1854

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
;
_exptl_absorpt_correction_T_min  0.93554
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4738
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.043609
_diffrn_orient_matrix_ub_12      -0.0763115
_diffrn_orient_matrix_ub_13      0.0478695
_diffrn_orient_matrix_ub_21      -0.0399145
_diffrn_orient_matrix_ub_22      -0.0212856
_diffrn_orient_matrix_ub_23      -0.1290778
_diffrn_orient_matrix_ub_31      0.0551791
_diffrn_orient_matrix_ub_32      -0.0164861
_diffrn_orient_matrix_ub_33      -0.0556492
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_number            3874
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         4.022
_diffrn_reflns_theta_max         67.341
_diffrn_reflns_theta_full        67.341
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.99
_diffrn_reflns_point_group_measured_fraction_max 0.989
_reflns_number_total             1719
_reflns_number_gt                1417
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Diamond (Brandenburg, K., (1999)'
_computing_publication_material  'WinGX Farrugia, L. J. (1999)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
The solvent was modelled as a methanol molecule disordered about a centre 
with 3bar symmetry. Methanol hydrogen atoms were located from residual
 electron density. Geometries and displacement parameters were restrained
to reasonable values.
The largest peak is 0.70 Angstoms from C14; the deepest hole is 0.73 
Angstroms from N1.


;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0512P)²+3.8356P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1719
_refine_ls_number_parameters     156
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.39489(8) 0.66231(8) 0.49598(15) 0.0298(4) Uani 1 d . .
C2 C 0.39844(8) 0.72747(8) 0.49636(15) 0.0298(4) Uani 1 d . .
H2 H 0.4431 0.7691 0.4969 0.036 Uiso 1 calc . .
C11 C 0.58320(8) 0.65158(8) 0.48098(17) 0.0333(4) Uani 1 d . .
C12 C 0.52761(8) 0.60507(8) 0.56216(16) 0.0316(4) Uani 1 d . .
C13 C 0.46608(8) 0.60845(8) 0.56756(16) 0.0303(4) Uani 1 d . .
H13 H 0.4285 0.5773 0.6219 0.036 Uiso 1 calc . .
C14 C 0.45996(8) 0.65753(8) 0.49317(16) 0.0305(4) Uani 1 d . .
C15 C 0.51596(9) 0.70248(9) 0.41243(16) 0.0336(4) Uani 1 d . .
H15 H 0.5112 0.7357 0.3611 0.04 Uiso 1 calc . .
C16 C 0.57771(9) 0.70028(9) 0.40482(17) 0.0359(4) Uani 1 d . .
H16 H 0.6149 0.731 0.3495 0.043 Uiso 1 calc . .
N1 N 0.63802(7) 0.63802(8) 0.49396(15) 0.0377(4) Uani 1 d . .
H1 H 0.6786 0.6606 0.4537 0.045 Uiso 1 calc . .
C21 C 0.61902(9) 0.58350(9) 0.58005(17) 0.0348(4) Uani 1 d . .
C22 C 0.65729(9) 0.55284(9) 0.62353(18) 0.0397(4) Uani 1 d . .
H22 H 0.7038 0.5687 0.5942 0.048 Uiso 1 calc . .
C23 C 0.62503(10) 0.49833(10) 0.71113(18) 0.0419(5) Uani 1 d . .
H23 H 0.65 0.4765 0.7427 0.05 Uiso 1 calc . .
C24 C 0.55669(10) 0.47464(10) 0.75422(17) 0.0402(4) Uani 1 d . .
H24 H 0.5358 0.4365 0.8132 0.048 Uiso 1 calc . .
C25 C 0.51893(9) 0.50572(9) 0.71247(17) 0.0370(4) Uani 1 d . .
H25 H 0.4725 0.4897 0.7426 0.044 Uiso 1 calc . .
C26 C 0.55051(8) 0.56122(9) 0.62503(16) 0.0321(4) Uani 1 d . .
C10 C 0.3287(19) 0.652(2) 0.162(7) 0.039(8) Uani 0.1667 d A -1
H10A H 0.3593 0.6634 0.0867 0.058 Uiso 0.1667 calc A -1
H10B H 0.3016 0.6011 0.1736 0.058 Uiso 0.1667 calc A -1
H10C H 0.3575 0.6738 0.239 0.058 Uiso 0.1667 calc A -1
O10 O 0.2834(7) 0.6777(10) 0.1443(11) 0.079(3) Uani 0.1667 d A -1
H1O H 0.2741 0.6766 0.0656 0.118 Uiso 0.1667 calc A -1



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.395(2) . ?
C1 C2 1.395(2) 3_565 ?
C1 C14 1.486(2) . ?
C2 C1 1.395(2) 2_665 ?
C2 H2 0.95 . ?
C11 C16 1.384(2) . ?
C11 N1 1.385(2) . ?
C11 C12 1.414(2) . ?
C12 C13 1.392(2) . ?
C12 C26 1.447(2) . ?
C13 C14 1.387(2) . ?
C13 H13 0.95 . ?
C14 C15 1.406(2) . ?
C15 C16 1.384(2) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
N1 C21 1.381(2) . ?
N1 H1 0.88 . ?
C21 C22 1.390(2) . ?
C21 C26 1.410(2) . ?
C22 C23 1.384(3) . ?
C22 H22 0.95 . ?
C23 C24 1.395(3) . ?
C23 H23 0.95 . ?
C24 C25 1.382(2) . ?
C24 H24 0.95 . ?
C25 C26 1.395(2) . ?
C25 H25 0.95 . ?
C10 O10 1.379(10) . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
O10 H1O 0.84 . ?

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 C2 118.77(15) . 3_565 ?
C2 C1 C14 120.74(14) . . ?
C2 C1 C14 120.49(14) 3_565 . ?
C1 C2 C1 121.23(16) . 2_665 ?
C1 C2 H2 119.4 . . ?
C1 C2 H2 119.4 2_665 . ?
C16 C11 N1 130.08(16) . . ?
C16 C11 C12 121.44(15) . . ?
N1 C11 C12 108.47(15) . . ?
C13 C12 C11 119.79(15) . . ?
C13 C12 C26 133.49(16) . . ?
C11 C12 C26 106.72(14) . . ?
C14 C13 C12 119.59(15) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 119.14(15) . . ?
C13 C14 C1 121.02(15) . . ?
C15 C14 C1 119.83(15) . . ?
C16 C15 C14 122.59(16) . . ?
C16 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C11 C16 C15 117.43(16) . . ?
C11 C16 H16 121.3 . . ?
C15 C16 H16 121.3 . . ?
C21 N1 C11 109.35(14) . . ?
C21 N1 H1 125.3 . . ?
C11 N1 H1 125.3 . . ?
N1 C21 C22 129.55(16) . . ?
N1 C21 C26 108.82(14) . . ?
C22 C21 C26 121.62(17) . . ?
C23 C22 C21 117.43(17) . . ?
C23 C22 H22 121.3 . . ?
C21 C22 H22 121.3 . . ?
C22 C23 C24 121.58(17) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C25 C24 C23 121.05(17) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C26 118.49(16) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?
C25 C26 C21 119.80(15) . . ?
C25 C26 C12 133.56(16) . . ?
C21 C26 C12 106.63(14) . . ?
O10 C10 H10A 109.5 . . ?
O10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O10 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C10 O10 H1O 109.5 . . ?

