# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_CrystalClear
_database_code_depnum_ccdc_archive 'CCDC 1818349'
_audit_update_record             
;
2018-01-21 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H56 N2 O4'
_chemical_formula_weight         628.86

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                   9.7956(7)
_cell_length_b                   17.7834(15)
_cell_length_c                   10.0007(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.394(3)
_cell_angle_gamma                90
_cell_volume                     1718.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    159(2)
_cell_measurement_reflns_used    8155
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_F_000             684
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      159(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn 724 plus'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12606
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.383
_diffrn_reflns_theta_max         27.542
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             3844
_reflns_number_gt                3291
_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    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0977P)²+0.1910P] 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         3844
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1481
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_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 0.97442(9) 0.94770(5) 0.14744(8) 0.0232(2) Uani 1 1 d . . . . .
N1 N 1.04049(10) 0.89586(5) 0.91032(9) 0.0174(2) Uani 1 1 d . . . . .
C003 C 1.12065(11) 0.96480(6) 0.46981(10) 0.0157(2) Uani 1 1 d . . . . .
C004 C 0.99037(11) 0.90873(6) 0.25502(11) 0.0181(3) Uani 1 1 d . . . . .
O2 O 1.00557(11) 0.84015(5) 0.26312(9) 0.0341(3) Uani 1 1 d . . . . .
H28 H 1.0014 0.8220 0.1850 0.051 Uiso 1 1 calc R U . . .
C006 C 1.12730(11) 1.01161(6) 0.58746(10) 0.0156(2) Uani 1 1 d . . . . .
C007 C 0.96024(12) 0.84290(6) 0.68080(11) 0.0194(3) Uani 1 1 d . . . . .
H2 H 1.0490 0.8167 0.6784 0.023 Uiso 1 1 calc R U . . .
H3 H 0.9683 0.8946 0.6462 0.023 Uiso 1 1 calc R U . . .
C008 C 1.24557(12) 0.93022(6) 0.44352(12) 0.0206(3) Uani 1 1 d . . . . .
H4 H 1.2431 0.8991 0.3659 0.025 Uiso 1 1 calc R U . . .
C009 C 1.27840(12) 0.92958(6) 1.00937(12) 0.0214(3) Uani 1 1 d . . . . .
H5 H 1.2677 0.9779 0.9595 0.026 Uiso 1 1 calc R U . . .
H6 H 1.2480 0.9372 1.0980 0.026 Uiso 1 1 calc R U . . .
C010 C 0.99401(11) 0.95409(6) 0.38386(10) 0.0156(2) Uani 1 1 d . . . . .
C011 C 1.37456(12) 0.98818(7) 0.64319(12) 0.0244(3) Uani 1 1 d . . . . .
H7 H 1.4606 0.9959 0.7007 0.029 Uiso 1 1 calc R U . . .
C012 C 0.93416(11) 0.84667(6) 0.82607(11) 0.0178(3) Uani 1 1 d . . . . .
H26 H 0.9405 0.7948 0.8651 0.021 Uiso 1 1 calc R U . . .
C013 C 1.36762(12) 0.94113(7) 0.52769(13) 0.0246(3) Uani 1 1 d . . . . .
H8 H 1.4490 0.9170 0.5090 0.030 Uiso 1 1 calc R U . . .
C014 C 1.18810(11) 0.86979(6) 0.92896(12) 0.0202(3) Uani 1 1 d . . . . .
H27 H 1.2164 0.8648 0.8377 0.024 Uiso 1 1 calc R U . . .
C015 C 0.84424(12) 0.80160(7) 0.58880(12) 0.0231(3) Uani 1 1 d . . . . .
H9 H 0.8601 0.8050 0.4937 0.028 Uiso 1 1 calc R U . . .
H10 H 0.8457 0.7478 0.6143 0.028 Uiso 1 1 calc R U . . .
C016 C 1.25820(12) 1.02233(7) 0.67190(11) 0.0201(3) Uani 1 1 d . . . . .
H11 H 1.2643 1.0538 0.7494 0.024 Uiso 1 1 calc R U . . .
C017 C 0.79165(12) 0.87901(7) 0.83515(13) 0.0253(3) Uani 1 1 d . . . . .
H12 H 0.7877 0.9322 0.8058 0.030 Uiso 1 1 calc R U . . .
H13 H 0.7758 0.8773 0.9304 0.030 Uiso 1 1 calc R U . . .
C018 C 0.70334(13) 0.83470(7) 0.59956(13) 0.0250(3) Uani 1 1 d . . . . .
H14 H 0.6982 0.8870 0.5650 0.030 Uiso 1 1 calc R U . . .
H15 H 0.6302 0.8050 0.5429 0.030 Uiso 1 1 calc R U . . .
C019 C 1.42978(13) 0.90595(8) 1.03184(14) 0.0287(3) Uani 1 1 d . . . . .
H16 H 1.4620 0.9018 0.9433 0.034 Uiso 1 1 calc R U . . .
H17 H 1.4864 0.9448 1.0861 0.034 Uiso 1 1 calc R U . . .
C020 C 0.67846(13) 0.83427(8) 0.74563(13) 0.0292(3) Uani 1 1 d . . . . .
H18 H 0.6782 0.7818 0.7787 0.035 Uiso 1 1 calc R U . . .
H19 H 0.5870 0.8568 0.7507 0.035 Uiso 1 1 calc R U . . .
C021 C 1.20475(14) 0.79364(7) 0.99960(15) 0.0318(3) Uani 1 1 d . . . . .
H20 H 1.1506 0.7553 0.9419 0.038 Uiso 1 1 calc R U . . .
H21 H 1.1686 0.7964 1.0863 0.038 Uiso 1 1 calc R U . . .
C022 C 1.44901(16) 0.83084(8) 1.10519(18) 0.0406(4) Uani 1 1 d . . . . .
H22 H 1.4248 0.8362 1.1970 0.049 Uiso 1 1 calc R U . . .
H23 H 1.5472 0.8154 1.1150 0.049 Uiso 1 1 calc R U . . .
C023 C 1.35787(16) 0.77061(8) 1.0270(2) 0.0454(4) Uani 1 1 d . . . . .
H24 H 1.3676 0.7232 1.0796 0.054 Uiso 1 1 calc R U . . .
H25 H 1.3899 0.7612 0.9396 0.054 Uiso 1 1 calc R U . . .
H1 H 1.0359(17) 0.9439(10) 0.8718(16) 0.034(4) Uiso 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
O1 C004 1.2677(13) . ?
N1 C014 1.5008(14) . ?
N1 C012 1.5078(14) . ?
C003 C010 1.4021(15) . ?
C003 C008 1.4316(15) . ?
C003 C006 1.4340(15) . ?
C004 O2 1.2298(14) . ?
C004 C010 1.5156(14) . ?
C006 C010 1.4063(15) 3_776 ?
C006 C016 1.4284(15) . ?
C007 C012 1.5171(15) . ?
C007 C015 1.5283(16) . ?
C008 C013 1.3590(17) . ?
C009 C019 1.5223(17) . ?
C009 C014 1.5256(16) . ?
C010 C006 1.4063(15) 3_776 ?
C011 C016 1.3628(17) . ?
C011 C013 1.4190(18) . ?
C012 C017 1.5261(16) . ?
C014 C021 1.5238(17) . ?
C015 C018 1.5203(17) . ?
C017 C020 1.5296(17) . ?
C018 C020 1.5197(17) . ?
C019 C022 1.521(2) . ?
C021 C023 1.5357(19) . ?
C022 C023 1.526(2) . ?

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
C014 N1 C012 116.99(8) . . ?
C010 C003 C008 121.75(10) . . ?
C010 C003 C006 119.93(10) . . ?
C008 C003 C006 118.31(10) . . ?
O2 C004 O1 126.49(10) . . ?
O2 C004 C010 119.08(10) . . ?
O1 C004 C010 114.41(9) . . ?
C010 C006 C016 121.90(10) 3_776 . ?
C010 C006 C003 119.50(10) 3_776 . ?
C016 C006 C003 118.60(10) . . ?
C012 C007 C015 111.89(9) . . ?
C013 C008 C003 121.12(11) . . ?
C019 C009 C014 110.64(10) . . ?
C003 C010 C006 120.56(10) . 3_776 ?
C003 C010 C004 119.29(9) . . ?
C006 C010 C004 120.06(9) 3_776 . ?
C016 C011 C013 120.25(11) . . ?
N1 C012 C007 110.60(9) . . ?
N1 C012 C017 107.66(9) . . ?
C007 C012 C017 111.85(9) . . ?
C008 C013 C011 120.58(11) . . ?
N1 C014 C021 111.12(10) . . ?
N1 C014 C009 108.30(9) . . ?
C021 C014 C009 111.47(10) . . ?
C018 C015 C007 111.45(9) . . ?
C011 C016 C006 121.13(11) . . ?
C012 C017 C020 110.61(10) . . ?
C020 C018 C015 110.86(10) . . ?
C022 C019 C009 110.78(11) . . ?
C018 C020 C017 110.20(10) . . ?
C014 C021 C023 110.32(12) . . ?
C019 C022 C023 110.70(12) . . ?
C022 C023 C021 112.15(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C010 C003 C006 C010 0.53(17) . . . 3_776 ?
C008 C003 C006 C010 -179.62(9) . . . 3_776 ?
C010 C003 C006 C016 -179.06(9) . . . . ?
C008 C003 C006 C016 0.78(15) . . . . ?
C010 C003 C008 C013 179.97(10) . . . . ?
C006 C003 C008 C013 0.13(17) . . . . ?
C008 C003 C010 C006 179.63(9) . . . 3_776 ?
C006 C003 C010 C006 -0.53(17) . . . 3_776 ?
C008 C003 C010 C004 -3.89(15) . . . . ?
C006 C003 C010 C004 175.95(9) . . . . ?
O2 C004 C010 C003 72.53(14) . . . . ?
O1 C004 C010 C003 -105.93(12) . . . . ?
O2 C004 C010 C006 -110.97(13) . . . 3_776 ?
O1 C004 C010 C006 70.57(13) . . . 3_776 ?
C014 N1 C012 C007 -64.15(12) . . . . ?
C014 N1 C012 C017 173.38(9) . . . . ?
C015 C007 C012 N1 -172.90(9) . . . . ?
C015 C007 C012 C017 -52.91(12) . . . . ?
C003 C008 C013 C011 -0.92(18) . . . . ?
C016 C011 C013 C008 0.77(19) . . . . ?
C012 N1 C014 C021 -60.60(12) . . . . ?
C012 N1 C014 C009 176.65(9) . . . . ?
C019 C009 C014 N1 179.82(9) . . . . ?
C019 C009 C014 C021 57.28(13) . . . . ?
C012 C007 C015 C018 53.14(13) . . . . ?
C013 C011 C016 C006 0.18(18) . . . . ?
C010 C006 C016 C011 179.48(10) 3_776 . . . ?
C003 C006 C016 C011 -0.94(17) . . . . ?
N1 C012 C017 C020 176.95(9) . . . . ?
C007 C012 C017 C020 55.25(13) . . . . ?
C007 C015 C018 C020 -56.00(13) . . . . ?
C014 C009 C019 C022 -57.71(14) . . . . ?
C015 C018 C020 C017 58.37(14) . . . . ?
C012 C017 C020 C018 -57.76(14) . . . . ?
N1 C014 C021 C023 -175.90(11) . . . . ?
C009 C014 C021 C023 -54.99(15) . . . . ?
C009 C019 C022 C023 56.59(17) . . . . ?
C019 C022 C023 C021 -55.2(2) . . . . ?
C014 C021 C023 C022 54.21(19) . . . . ?

_refine_diff_density_max         0.760
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
