# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_150717f
_database_code_depnum_ccdc_archive 'CCDC 1449860'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 N2 O4'
_chemical_formula_weight         414.45

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.398(6)
_cell_length_b                   11.272(5)
_cell_length_c                   16.887(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.340(7)
_cell_angle_gamma                90.00
_cell_volume                     2146.7(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1982
_cell_measurement_theta_min      2.438
_cell_measurement_theta_max      21.172

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9591
_exptl_absorpt_correction_T_max  0.9658
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10526
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3780
_reflns_number_gt                1882
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0240P)²+0.5465P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3780
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.33108(16) 0.65408(19) 0.16565(12) 0.0595(6) Uani 1 1 d . . .
N2 N 0.32897(19) 0.83138(19) 0.37312(12) 0.0652(6) Uani 1 1 d . . .
O1 O 0.37778(13) 0.75089(14) 0.20933(9) 0.0590(5) Uani 1 1 d . . .
O2 O 0.14563(15) 0.65874(17) 0.20413(11) 0.0838(6) Uani 1 1 d . . .
O3 O 0.49292(15) 0.61437(17) 0.10394(10) 0.0797(6) Uani 1 1 d . . .
O4 O 0.59090(16) 0.57234(17) 0.30989(12) 0.0893(6) Uani 1 1 d . . .
C1 C 0.2142(2) 0.6178(2) 0.16429(15) 0.0587(7) Uani 1 1 d . . .
C2 C 0.3914(2) 0.5959(2) 0.11162(14) 0.0572(7) Uani 1 1 d . . .
C3 C 0.3044(2) 0.5102(2) 0.07234(14) 0.0529(6) Uani 1 1 d . . .
C4 C 0.2009(2) 0.5213(2) 0.10450(14) 0.0573(7) Uani 1 1 d . . .
C5 C 0.1066(3) 0.4500(3) 0.08010(18) 0.0906(10) Uani 1 1 d . . .
H5 H 0.0370 0.4563 0.1025 0.109 Uiso 1 1 calc R . .
C6 C 0.1173(3) 0.3679(3) 0.0211(2) 0.1116(12) Uani 1 1 d . . .
H6 H 0.0535 0.3189 0.0029 0.134 Uiso 1 1 calc R . .
C7 C 0.2206(3) 0.3575(3) -0.01120(17) 0.0910(10) Uani 1 1 d . . .
H7 H 0.2257 0.3011 -0.0508 0.109 Uiso 1 1 calc R . .
C8 C 0.3166(2) 0.4289(3) 0.01400(15) 0.0708(8) Uani 1 1 d . . .
H8 H 0.3867 0.4222 -0.0077 0.085 Uiso 1 1 calc R . .
C9 C 0.4394(2) 0.8196(2) 0.34154(15) 0.0671(7) Uani 1 1 d . . .
H9A H 0.5035 0.8115 0.3857 0.081 Uiso 1 1 calc R . .
H9B H 0.4534 0.8915 0.3127 0.081 Uiso 1 1 calc R . .
C10 C 0.4416(2) 0.7140(2) 0.28577(14) 0.0562(7) Uani 1 1 d . . .
H10 H 0.3972 0.6491 0.3062 0.067 Uiso 1 1 calc R . .
C11 C 0.5671(2) 0.6701(2) 0.28158(14) 0.0581(7) Uani 1 1 d . . .
C12 C 0.6584(2) 0.7432(2) 0.25140(13) 0.0509(6) Uani 1 1 d . . .
C13 C 0.7750(2) 0.7061(2) 0.26778(15) 0.0633(7) Uani 1 1 d . . .
H13 H 0.7933 0.6381 0.2983 0.076 Uiso 1 1 calc R . .
C14 C 0.8642(2) 0.7680(3) 0.23983(16) 0.0716(8) Uani 1 1 d . . .
H14 H 0.9420 0.7415 0.2521 0.086 Uiso 1 1 calc R . .
C15 C 0.8406(2) 0.8688(3) 0.19388(16) 0.0642(7) Uani 1 1 d . . .
C16 C 0.7244(2) 0.9052(2) 0.17752(14) 0.0624(7) Uani 1 1 d . . .
H16 H 0.7064 0.9728 0.1465 0.075 Uiso 1 1 calc R . .
C17 C 0.6339(2) 0.8445(2) 0.20571(14) 0.0595(7) Uani 1 1 d . . .
H17 H 0.5562 0.8717 0.1940 0.071 Uiso 1 1 calc R . .
C18 C 0.9385(2) 0.9369(3) 0.16363(18) 0.1014(11) Uani 1 1 d . . .
H18A H 0.9615 1.0024 0.1988 0.152 Uiso 1 1 calc R . .
H18B H 0.9110 0.9661 0.1108 0.152 Uiso 1 1 calc R . .
H18C H 1.0053 0.8856 0.1620 0.152 Uiso 1 1 calc R . .
C19 C 0.2994(2) 0.7489(2) 0.42758(15) 0.0616(7) Uani 1 1 d . . .
C20 C 0.3834(3) 0.6741(3) 0.46938(16) 0.0776(8) Uani 1 1 d . . .
H20 H 0.4611 0.6768 0.4586 0.093 Uiso 1 1 calc R . .
C21 C 0.3550(4) 0.5969(3) 0.52584(18) 0.0978(11) Uani 1 1 d . . .
H21 H 0.4136 0.5487 0.5532 0.117 Uiso 1 1 calc R . .
C22 C 0.2422(4) 0.5894(3) 0.5427(2) 0.1127(13) Uani 1 1 d . . .
H22 H 0.2232 0.5372 0.5815 0.135 Uiso 1 1 calc R . .
C23 C 0.1575(3) 0.6604(3) 0.5012(2) 0.1110(12) Uani 1 1 d . . .
H23 H 0.0796 0.6550 0.5114 0.133 Uiso 1 1 calc R . .
C24 C 0.1848(3) 0.7399(3) 0.44456(17) 0.0845(9) Uani 1 1 d . . .
H24 H 0.1257 0.7879 0.4176 0.101 Uiso 1 1 calc R . .
C25 C 0.2374(2) 0.9020(2) 0.32712(16) 0.0815(9) Uani 1 1 d . . .
H25A H 0.1813 0.8506 0.2961 0.122 Uiso 1 1 calc R . .
H25B H 0.2725 0.9537 0.2919 0.122 Uiso 1 1 calc R . .
H25C H 0.1977 0.9485 0.3628 0.122 Uiso 1 1 calc R . .


_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
N1 O1 1.380(2) . ?
N1 C2 1.385(3) . ?
N1 C1 1.390(3) . ?
N2 C19 1.384(3) . ?
N2 C9 1.443(3) . ?
N2 C25 1.446(3) . ?
O1 C10 1.448(3) . ?
O2 C1 1.196(3) . ?
O3 C2 1.201(3) . ?
O4 C11 1.217(3) . ?
C1 C4 1.477(3) . ?
C2 C3 1.472(3) . ?
C3 C8 1.367(3) . ?
C3 C4 1.375(3) . ?
C4 C5 1.357(3) . ?
C5 C6 1.378(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.375(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.521(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.524(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.475(3) . ?
C12 C13 1.382(3) . ?
C12 C17 1.384(3) . ?
C13 C14 1.372(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(3) . ?
C15 C18 1.503(3) . ?
C16 C17 1.380(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C24 1.380(4) . ?
C19 C20 1.389(3) . ?
C20 C21 1.365(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.359(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.366(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.379(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
O1 N1 C2 122.46(19) . . ?
O1 N1 C1 122.4(2) . . ?
C2 N1 C1 114.6(2) . . ?
C19 N2 C9 119.6(2) . . ?
C19 N2 C25 120.0(2) . . ?
C9 N2 C25 116.9(2) . . ?
N1 O1 C10 110.75(17) . . ?
O2 C1 N1 125.5(3) . . ?
O2 C1 C4 131.1(2) . . ?
N1 C1 C4 103.4(2) . . ?
O3 C2 N1 124.6(2) . . ?
O3 C2 C3 131.4(2) . . ?
N1 C2 C3 104.0(2) . . ?
C8 C3 C4 121.9(2) . . ?
C8 C3 C2 129.3(2) . . ?
C4 C3 C2 108.9(2) . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 C1 130.0(3) . . ?
C3 C4 C1 109.1(2) . . ?
C4 C5 C6 117.9(3) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 121.1(3) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C3 C8 C7 117.2(3) . . ?
C3 C8 H8 121.4 . . ?
C7 C8 H8 121.4 . . ?
N2 C9 C10 113.2(2) . . ?
N2 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N2 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
O1 C10 C9 106.01(19) . . ?
O1 C10 C11 113.90(19) . . ?
C9 C10 C11 112.5(2) . . ?
O1 C10 H10 108.1 . . ?
C9 C10 H10 108.1 . . ?
C11 C10 H10 108.1 . . ?
O4 C11 C12 120.8(2) . . ?
O4 C11 C10 115.7(2) . . ?
C12 C11 C10 123.3(2) . . ?
C13 C12 C17 118.1(2) . . ?
C13 C12 C11 118.0(2) . . ?
C17 C12 C11 123.9(2) . . ?
C14 C13 C12 121.1(2) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 117.5(2) . . ?
C16 C15 C18 121.3(3) . . ?
C14 C15 C18 121.2(3) . . ?
C15 C16 C17 122.0(2) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C16 C17 C12 120.1(2) . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 N2 121.1(3) . . ?
C24 C19 C20 117.0(3) . . ?
N2 C19 C20 121.9(3) . . ?
C21 C20 C19 121.7(3) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C22 C21 C20 120.9(3) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 118.5(3) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
C22 C23 C24 121.4(3) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C19 120.5(3) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
C2 N1 O1 C10 -92.0(2) . . . . ?
C1 N1 O1 C10 97.0(2) . . . . ?
O1 N1 C1 O2 -6.0(4) . . . . ?
C2 N1 C1 O2 -177.6(3) . . . . ?
O1 N1 C1 C4 174.29(19) . . . . ?
C2 N1 C1 C4 2.7(3) . . . . ?
O1 N1 C2 O3 8.7(4) . . . . ?
C1 N1 C2 O3 -179.7(2) . . . . ?
O1 N1 C2 C3 -173.15(18) . . . . ?
C1 N1 C2 C3 -1.6(3) . . . . ?
O3 C2 C3 C8 -1.6(5) . . . . ?
N1 C2 C3 C8 -179.6(2) . . . . ?
O3 C2 C3 C4 177.6(3) . . . . ?
N1 C2 C3 C4 -0.4(3) . . . . ?
C8 C3 C4 C5 1.0(4) . . . . ?
C2 C3 C4 C5 -178.3(2) . . . . ?
C8 C3 C4 C1 -178.7(2) . . . . ?
C2 C3 C4 C1 2.0(3) . . . . ?
O2 C1 C4 C5 -2.1(5) . . . . ?
N1 C1 C4 C5 177.5(3) . . . . ?
O2 C1 C4 C3 177.6(3) . . . . ?
N1 C1 C4 C3 -2.8(3) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C1 C4 C5 C6 178.4(3) . . . . ?
C4 C5 C6 C7 0.9(5) . . . . ?
C5 C6 C7 C8 -0.3(6) . . . . ?
C4 C3 C8 C7 -0.4(4) . . . . ?
C2 C3 C8 C7 178.8(2) . . . . ?
C6 C7 C8 C3 0.0(4) . . . . ?
C19 N2 C9 C10 69.3(3) . . . . ?
C25 N2 C9 C10 -89.7(3) . . . . ?
N1 O1 C10 C9 -154.75(18) . . . . ?
N1 O1 C10 C11 81.0(2) . . . . ?
N2 C9 C10 O1 79.7(2) . . . . ?
N2 C9 C10 C11 -155.2(2) . . . . ?
O1 C10 C11 O4 -126.5(2) . . . . ?
C9 C10 C11 O4 112.9(3) . . . . ?
O1 C10 C11 C12 58.2(3) . . . . ?
C9 C10 C11 C12 -62.4(3) . . . . ?
O4 C11 C12 C13 -10.2(4) . . . . ?
C10 C11 C12 C13 164.8(2) . . . . ?
O4 C11 C12 C17 167.8(2) . . . . ?
C10 C11 C12 C17 -17.2(4) . . . . ?
C17 C12 C13 C14 0.2(4) . . . . ?
C11 C12 C13 C14 178.3(2) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C13 C14 C15 C18 179.7(2) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C18 C15 C16 C17 -179.2(2) . . . . ?
C15 C16 C17 C12 -0.5(4) . . . . ?
C13 C12 C17 C16 0.3(3) . . . . ?
C11 C12 C17 C16 -177.7(2) . . . . ?
C9 N2 C19 C24 -164.4(2) . . . . ?
C25 N2 C19 C24 -6.1(4) . . . . ?
C9 N2 C19 C20 17.6(4) . . . . ?
C25 N2 C19 C20 175.9(2) . . . . ?
C24 C19 C20 C21 -1.3(4) . . . . ?
N2 C19 C20 C21 176.8(3) . . . . ?
C19 C20 C21 C22 0.7(5) . . . . ?
C20 C21 C22 C23 0.6(6) . . . . ?
C21 C22 C23 C24 -1.3(6) . . . . ?
C22 C23 C24 C19 0.7(5) . . . . ?
N2 C19 C24 C23 -177.5(3) . . . . ?
C20 C19 C24 C23 0.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.039
