# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_4n
_database_code_depnum_ccdc_archive 'CCDC 1557855'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-11-10 downloaded from the CCDC.
;
# 2456GuillotICMMO
# echantillon italie 4228 via david du cp3a

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 N2 O4'
_chemical_formula_sum            'C24 H22 N2 O4'
_chemical_formula_weight         402.43

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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

_cell_length_a                   19.2545(11)
_cell_length_b                   15.5146(10)
_cell_length_c                   13.4314(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4012.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    8786
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      30.26

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9587
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41326
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.686
_diffrn_reflns_theta_max         30.560
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6103
_reflns_number_gt                3368
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0801P)²+2.9167P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6103
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1918
_refine_ls_wR_factor_gt          0.1431
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
C1 C 0.06607(10) 0.03096(11) 0.21252(16) 0.0251(4) Uani 1 1 d . . . . .
C4 C 0.13239(11) 0.08525(13) 0.22007(18) 0.0298(5) Uani 1 1 d . . . . .
H4A H 0.1366 0.1299 0.1677 0.036 Uiso 1 1 calc R U . . .
H4B H 0.1755 0.0507 0.2253 0.036 Uiso 1 1 calc R U . . .
C5 C 0.09650(12) -0.07348(13) 0.09051(17) 0.0305(5) Uani 1 1 d . . . . .
H5A H 0.1346 -0.0333 0.0733 0.037 Uiso 1 1 calc R U . . .
H5B H 0.0586 -0.0663 0.0414 0.037 Uiso 1 1 calc R U . . .
C6 C 0.18441(11) -0.18489(12) 0.13713(17) 0.0297(5) Uani 1 1 d . . . . .
H6 H 0.2118 -0.1400 0.1649 0.036 Uiso 1 1 calc R U . . .
C7 C 0.20724(11) -0.26958(13) 0.14367(17) 0.0292(5) Uani 1 1 d . . . . .
H7 H 0.2500 -0.2826 0.1756 0.035 Uiso 1 1 calc R U . . .
C8 C 0.16715(11) -0.33503(12) 0.10325(17) 0.0275(5) Uani 1 1 d . . . . .
C9 C 0.10506(11) -0.31577(13) 0.05327(18) 0.0319(5) Uani 1 1 d . . . . .
H9 H 0.0783 -0.3604 0.0237 0.038 Uiso 1 1 calc R U . . .
C10 C 0.08325(12) -0.23099(13) 0.04758(18) 0.0324(5) Uani 1 1 d . . . . .
H10 H 0.0412 -0.2175 0.0140 0.039 Uiso 1 1 calc R U . . .
C11 C 0.12233(11) -0.16501(12) 0.09066(17) 0.0281(5) Uani 1 1 d . . . . .
C12 C 0.19052(11) -0.42325(12) 0.10886(17) 0.0283(5) Uani 1 1 d . . . . .
C15 C -0.10560(11) 0.11994(13) 0.17920(18) 0.0305(5) Uani 1 1 d . . . . .
H15A H -0.1403 0.1170 0.1249 0.037 Uiso 1 1 calc R U . . .
H15B H -0.0848 0.1782 0.1834 0.037 Uiso 1 1 calc R U . . .
C16 C -0.05190(10) 0.04671(12) 0.17658(17) 0.0259(4) Uani 1 1 d . . . . .
H16 H -0.0674 -0.0026 0.1342 0.031 Uiso 1 1 calc R U . . .
N1 N 0.20949(10) -0.49357(11) 0.11223(16) 0.0361(5) Uani 1 1 d . . . . .
O1 O 0.01708(7) 0.07424(8) 0.15282(11) 0.0253(3) Uani 1 1 d . . . . .
O2 O 0.07165(8) -0.05694(8) 0.18947(11) 0.0268(3) Uani 1 1 d . . . . .
C17 C -0.04374(11) 0.39536(12) 0.33367(17) 0.0272(5) Uani 1 1 d . . . . .
H17 H -0.0549 0.4448 0.3787 0.033 Uiso 1 1 calc R U . . .
C18 C -0.09618(12) 0.32155(14) 0.34443(19) 0.0347(5) Uani 1 1 d . . . . .
H18A H -0.1246 0.3248 0.4057 0.042 Uiso 1 1 calc R U . . .
H18B H -0.0755 0.2635 0.3364 0.042 Uiso 1 1 calc R U . . .
C19 C 0.06938(10) 0.41073(12) 0.27178(17) 0.0268(5) Uani 1 1 d . . . . .
C20 C 0.13391(11) 0.35532(13) 0.25023(19) 0.0334(5) Uani 1 1 d . . . . .
H20A H 0.1429 0.3103 0.3009 0.040 Uiso 1 1 calc R U . . .
H20B H 0.1763 0.3892 0.2360 0.040 Uiso 1 1 calc R U . . .
C21 C 0.18559(11) 0.87434(12) 0.39462(18) 0.0297(5) Uani 1 1 d . . . . .
C22 C 0.16724(11) 0.78423(12) 0.39031(17) 0.0267(4) Uani 1 1 d . . . . .
C23 C 0.21713(11) 0.72278(12) 0.41440(17) 0.0277(5) Uani 1 1 d . . . . .
H23 H 0.2625 0.7402 0.4337 0.033 Uiso 1 1 calc R U . . .
C24 C 0.10082(11) 0.75924(13) 0.35987(18) 0.0315(5) Uani 1 1 d . . . . .
H24 H 0.0673 0.8013 0.3418 0.038 Uiso 1 1 calc R U . . .
C25 C 0.20027(11) 0.63610(12) 0.41008(17) 0.0279(5) Uani 1 1 d . . . . .
H25 H 0.2342 0.5940 0.4266 0.034 Uiso 1 1 calc R U . . .
C26 C 0.13424(11) 0.61030(12) 0.38180(17) 0.0281(5) Uani 1 1 d . . . . .
C27 C 0.08441(11) 0.67221(13) 0.35642(19) 0.0328(5) Uani 1 1 d . . . . .
H27 H 0.0392 0.6546 0.3368 0.039 Uiso 1 1 calc R U . . .
C28 C 0.11628(12) 0.51603(12) 0.38077(18) 0.0320(5) Uani 1 1 d . . . . .
H28A H 0.1592 0.4809 0.3819 0.038 Uiso 1 1 calc R U . . .
H28B H 0.0882 0.5012 0.4401 0.038 Uiso 1 1 calc R U . . .
N2 N 0.20086(10) 0.94579(11) 0.39824(17) 0.0390(5) Uani 1 1 d . . . . .
O3 O 0.02735(7) 0.36896(9) 0.34238(12) 0.0285(3) Uani 1 1 d . . . . .
O4 O 0.07777(7) 0.49900(9) 0.29217(12) 0.0296(4) Uani 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
C1 O2 1.403(2) . ?
C1 O1 1.408(2) . ?
C1 C4 1.533(3) . ?
C1 C16 1.534(3) 3 ?
C4 C15 1.545(3) 3 ?
C5 O2 1.436(3) . ?
C5 C11 1.505(3) . ?
C6 C11 1.383(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.386(3) . ?
C8 C9 1.403(3) . ?
C8 C12 1.443(3) . ?
C9 C10 1.383(3) . ?
C10 C11 1.396(3) . ?
C12 N1 1.152(3) . ?
C15 C16 1.537(3) . ?
C15 C4 1.545(3) 3 ?
C16 O1 1.431(2) . ?
C16 C1 1.534(3) 3 ?
C17 O3 1.434(2) . ?
C17 C19 1.519(3) 3 ?
C17 C18 1.533(3) . ?
C18 C20 1.555(4) 3 ?
C19 O3 1.405(2) . ?
C19 O4 1.406(2) . ?
C19 C17 1.519(3) 3 ?
C19 C20 1.538(3) . ?
C20 C18 1.555(4) 3 ?
C21 N2 1.148(3) . ?
C21 C22 1.443(3) . ?
C22 C23 1.392(3) . ?
C22 C24 1.397(3) . ?
C23 C25 1.385(3) . ?
C24 C27 1.387(3) . ?
C25 C26 1.386(3) . ?
C26 C27 1.400(3) . ?
C26 C28 1.503(3) . ?
C28 O4 1.427(3) . ?

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
O2 C1 O1 112.90(16) . . ?
O2 C1 C4 119.01(16) . . ?
O1 C1 C4 109.49(15) . . ?
O2 C1 C16 112.51(16) . 3 ?
O1 C1 C16 110.97(16) . 3 ?
C4 C1 C16 89.80(16) . 3 ?
C1 C4 C15 88.35(15) . 3 ?
O2 C5 C11 106.12(17) . . ?
C11 C6 C7 120.88(19) . . ?
C8 C7 C6 119.5(2) . . ?
C7 C8 C9 120.39(18) . . ?
C7 C8 C12 120.0(2) . . ?
C9 C8 C12 119.51(19) . . ?
C10 C9 C8 119.19(19) . . ?
C9 C10 C11 120.7(2) . . ?
C6 C11 C10 119.30(18) . . ?
C6 C11 C5 119.78(19) . . ?
C10 C11 C5 120.9(2) . . ?
N1 C12 C8 179.2(3) . . ?
C16 C15 C4 89.27(15) . 3 ?
O1 C16 C1 115.42(17) . 3 ?
O1 C16 C15 114.14(15) . . ?
C1 C16 C15 88.62(16) 3 . ?
C1 O1 C16 110.62(14) . . ?
C1 O2 C5 113.81(15) . . ?
O3 C17 C19 115.55(18) . 3 ?
O3 C17 C18 114.06(16) . . ?
C19 C17 C18 89.49(17) 3 . ?
C17 C18 C20 88.79(16) . 3 ?
O3 C19 O4 112.58(17) . . ?
O3 C19 C17 111.70(16) . 3 ?
O4 C19 C17 111.84(16) . 3 ?
O3 C19 C20 109.55(16) . . ?
O4 C19 C20 119.22(16) . . ?
C17 C19 C20 89.96(17) 3 . ?
C19 C20 C18 87.98(16) . 3 ?
N2 C21 C22 179.3(2) . . ?
C23 C22 C24 120.64(18) . . ?
C23 C22 C21 119.04(19) . . ?
C24 C22 C21 120.30(19) . . ?
C25 C23 C22 119.58(19) . . ?
C27 C24 C22 119.22(19) . . ?
C23 C25 C26 120.48(19) . . ?
C25 C26 C27 119.82(18) . . ?
C25 C26 C28 119.65(18) . . ?
C27 C26 C28 120.52(19) . . ?
C24 C27 C26 120.2(2) . . ?
O4 C28 C26 107.90(17) . . ?
C19 O3 C17 111.30(15) . . ?
C19 O4 C28 113.74(15) . . ?

_refine_diff_density_max         0.529
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.068

