# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1867850'
_audit_update_record             
;
2018-09-14 deposited with the CCDC.
2018-11-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H28 N4 O5'
_chemical_formula_weight         572.60

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      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

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

_cell_length_a                   16.631(3)
_cell_length_b                   30.140(5)
_cell_length_c                   6.2400(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3127.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    730
_cell_measurement_theta_min      1.351
_cell_measurement_theta_max      27.140

_exptl_crystal_description       niddle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   0.6033
_exptl_transmission_factor_max   0.7045
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(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            8905
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.351
_diffrn_reflns_theta_max         27.140
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.697
_diffrn_reflns_point_group_measured_fraction_full 0.719
_reflns_number_total             2406
_reflns_number_gt                1612
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.287
_reflns_Friedel_fraction_max     0.344
_reflns_Friedel_fraction_full    0.386

_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-2017/1 (Sheldrick, 2017)'
_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)+(0.1965P)²] 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     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.046(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 323 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.8(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2406
_refine_ls_number_parameters     201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0911
_refine_ls_wR_factor_ref         0.3040
_refine_ls_wR_factor_gt          0.2711
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_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 0.1930(3) 0.42039(15) 0.2120(9) 0.0482(14) Uani 1 1 d . . . . .
H1 H 0.214190 0.408796 0.320611 0.072 Uiso 1 1 calc R U . . .
O2 O 0.1188(3) 0.44573(17) -0.1369(10) 0.0580(15) Uani 1 1 d . . . . .
N1 N 0.2323(3) 0.35764(17) 0.4761(8) 0.0342(13) Uani 1 1 d . . . . .
N2 N 0.3201(3) 0.28356(18) 0.8934(9) 0.0388(14) Uani 1 1 d . . . . .
C1 C 0.1527(4) 0.3895(2) 0.1026(11) 0.0390(17) Uani 1 1 d . . . . .
C2 C 0.1114(4) 0.4013(3) -0.0882(12) 0.0455(19) Uani 1 1 d . . . . .
C3 C 0.0691(4) 0.3705(3) -0.2037(12) 0.0482(19) Uani 1 1 d . . . . .
H3 H 0.040542 0.379228 -0.328789 0.058 Uiso 1 1 calc R U . . .
C4 C 0.0680(4) 0.3272(2) -0.1383(13) 0.0444(17) Uani 1 1 d . . . . .
H4 H 0.039422 0.305786 -0.220125 0.053 Uiso 1 1 calc R U . . .
C5 C 0.1078(4) 0.3142(2) 0.0446(12) 0.0405(16) Uani 1 1 d . . . . .
H5 H 0.106338 0.283940 0.087406 0.049 Uiso 1 1 calc R U . . .
C6 C 0.1500(3) 0.3446(2) 0.1670(11) 0.0345(14) Uani 1 1 d . . . . .
C7 C 0.0813(6) 0.4600(3) -0.3345(15) 0.076(3) Uani 1 1 d . . . . .
H7A H 0.102718 0.442528 -0.454161 0.114 Uiso 1 1 calc R U . . .
H7B H 0.092719 0.491476 -0.358413 0.114 Uiso 1 1 calc R U . . .
H7C H 0.023027 0.455529 -0.324854 0.114 Uiso 1 1 calc R U . . .
C8 C 0.1910(3) 0.3300(2) 0.3577(10) 0.0322(14) Uani 1 1 d . . . . .
H8 H 0.188061 0.299660 0.398358 0.039 Uiso 1 1 calc R U . . .
C9 C 0.2733(3) 0.3429(2) 0.6609(10) 0.0347(15) Uani 1 1 d . . . . .
C10 C 0.2819(4) 0.2974(2) 0.7216(11) 0.0386(15) Uani 1 1 d . . . . .
H10 H 0.258296 0.275586 0.631212 0.046 Uiso 1 1 calc R U . . .
C11 C 0.3549(4) 0.3152(2) 1.0220(10) 0.0354(15) Uani 1 1 d . . . . .
C12 C 0.3957(4) 0.3002(3) 1.2071(11) 0.0438(17) Uani 1 1 d . . . . .
H12 H 0.398322 0.269484 1.239686 0.053 Uiso 1 1 calc R U . . .
C13 C 0.4317(4) 0.3310(3) 1.3395(12) 0.051(2) Uani 1 1 d . . . . .
H13 H 0.459522 0.321223 1.463876 0.061 Uiso 1 1 calc R U . . .
C14 C 0.4281(4) 0.3750(3) 1.2952(14) 0.054(2) Uani 1 1 d . . . . .
H14 H 0.453649 0.395415 1.389386 0.064 Uiso 1 1 calc R U . . .
C15 C 0.3883(4) 0.3911(3) 1.1165(12) 0.0471(19) Uani 1 1 d . . . . .
H15 H 0.385903 0.422025 1.088968 0.057 Uiso 1 1 calc R U . . .
C16 C 0.3513(4) 0.3606(2) 0.9759(11) 0.0351(15) Uani 1 1 d . . . . .
C17 C 0.3091(4) 0.3739(2) 0.7879(11) 0.0352(15) Uani 1 1 d . . . . .
H17 H 0.305912 0.404417 0.751197 0.042 Uiso 1 1 calc R U . . .
O100 O 0.2945(17) 0.5007(9) 1.012(14) 0.58(7) Uani 0.5 1 d . . P . .


_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 C1 1.335(8) . ?
O1 H1 0.8400 . ?
O2 C2 1.378(9) . ?
O2 C7 1.447(10) . ?
N1 C8 1.308(8) . ?
N1 C9 1.411(7) . ?
N2 C10 1.314(8) . ?
N2 C11 1.374(8) . ?
C1 C6 1.413(10) . ?
C1 C2 1.420(10) . ?
C2 C3 1.370(11) . ?
C3 C4 1.369(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(10) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(9) . ?
C5 H5 0.9500 . ?
C6 C8 1.441(9) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8 0.9500 . ?
C9 C17 1.362(9) . ?
C9 C10 1.431(9) . ?
C10 H10 0.9500 . ?
C11 C16 1.398(9) . ?
C11 C12 1.414(9) . ?
C12 C13 1.379(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.357(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(11) . ?
C14 H14 0.9500 . ?
C15 C16 1.412(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.425(9) . ?
C17 H17 0.9500 . ?

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 O1 H1 109.5 . . ?
C2 O2 C7 115.9(7) . . ?
C8 N1 C9 121.0(5) . . ?
C10 N2 C11 117.4(5) . . ?
O1 C1 C6 122.6(6) . . ?
O1 C1 C2 119.8(6) . . ?
C6 C1 C2 117.6(7) . . ?
O2 C2 C3 126.0(7) . . ?
O2 C2 C1 112.6(7) . . ?
C3 C2 C1 121.4(7) . . ?
C4 C3 C2 119.7(6) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.9(7) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.8(6) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.6(6) . . ?
C5 C6 C8 119.6(6) . . ?
C1 C6 C8 120.8(6) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C6 121.4(6) . . ?
N1 C8 H8 119.3 . . ?
C6 C8 H8 119.3 . . ?
C17 C9 N1 118.1(6) . . ?
C17 C9 C10 117.4(6) . . ?
N1 C9 C10 124.5(6) . . ?
N2 C10 C9 124.6(6) . . ?
N2 C10 H10 117.7 . . ?
C9 C10 H10 117.7 . . ?
N2 C11 C16 122.7(6) . . ?
N2 C11 C12 117.2(6) . . ?
C16 C11 C12 120.0(6) . . ?
C13 C12 C11 118.9(7) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 121.1(7) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 121.8(8) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C16 118.8(7) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C11 C16 C15 119.3(6) . . ?
C11 C16 C17 117.8(6) . . ?
C15 C16 C17 122.9(6) . . ?
C9 C17 C16 120.1(6) . . ?
C9 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7A O1 0.98 2.65 3.589(11) 159.8 1_554 yes
C7 H7B O2 0.98 2.61 3.468(11) 146.9 7_454 yes
C8 H8 N2 0.95 2.51 3.435(9) 163.8 6_554 yes
C10 H10 N2 0.95 2.66 3.608(9) 175.0 6_554 yes
C7 H7A O1 0.98 2.65 3.589(11) 159.8 1_554 yes
C7 H7B O2 0.98 2.61 3.468(11) 146.9 7_454 yes
C8 H8 N2 0.95 2.51 3.435(9) 163.8 6_554 yes
C10 H10 N2 0.95 2.66 3.608(9) 175.0 6_554 yes

_refine_diff_density_max         0.975
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.168



