# 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_EA879
_database_code_depnum_ccdc_archive 'CCDC 1565838'
_audit_update_record             
;
2017-07-31 deposited with the CCDC.
2017-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'  3-methyl-2-oxo-5-((E)-(2-oxo-4,8b-dihydro-2H-indeno[1,2-b]furan-3(3aH)-ylidene) methoxy)-2,5-dihydro-1H-pyrrole-1-carboxylate '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 N O6'
_chemical_formula_weight         397.41
_chemical_absolute_configuration ad

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           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.0736(13)
_cell_length_b                   10.7768(12)
_cell_length_c                   21.461(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2098.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1659
_cell_measurement_theta_min      4.5450
_cell_measurement_theta_max      53.1930

_exptl_crystal_description       platelett
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840.0
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91030
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.888
_oxdiff_exptl_absorpt_empirical_full_max 1.131
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2890
_diffrn_standards_number         11813
_diffrn_reflns_number            11775
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_av_sigmaI/netI    0.0611
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         66.58
_reflns_number_total             3745
_reflns_number_gt                2172
_reflns_threshold_expression     >2sigma(I)

_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_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0419P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_number_reflns         3745
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
O2 O 0.1502(3) 1.1817(2) 0.87059(11) 0.0710(7) Uani 1 1 d . . .
O4 O 0.6569(3) 0.5502(2) 0.96520(12) 0.0844(8) Uani 1 1 d . . .
O3 O 0.4598(3) 0.8448(2) 0.85544(11) 0.0657(6) Uani 1 1 d . . .
C13 C 0.4408(4) 0.9694(3) 0.85209(16) 0.0612(9) Uani 1 1 d . . .
H13 H 0.5212 1.0205 0.8441 0.073 Uiso 1 1 calc R . .
N1 N 0.6251(3) 0.7478(3) 0.92414(12) 0.0620(7) Uani 1 1 d . . .
C2 C 0.3094(4) 1.0188(3) 0.86012(16) 0.0552(9) Uani 1 1 d . . .
O1 O 0.3783(3) 1.2320(2) 0.84155(13) 0.0837(8) Uani 1 1 d . . .
C6 C -0.0223(4) 0.9392(3) 0.80065(17) 0.0629(9) Uani 1 1 d . . .
C17 C 0.6234(4) 0.6872(3) 0.82147(16) 0.0689(10) Uani 1 1 d . . .
H17 H 0.6199 0.6891 0.7782 0.083 Uiso 1 1 calc R . .
C1 C 0.2913(5) 1.1532(3) 0.85541(17) 0.0635(10) Uani 1 1 d . . .
C14 C 0.6069(4) 0.7988(3) 0.86205(16) 0.0613(9) Uani 1 1 d . . .
H14 H 0.6807 0.8625 0.8527 0.074 Uiso 1 1 calc R . .
C15 C 0.6429(4) 0.6183(3) 0.92187(18) 0.0655(9) Uani 1 1 d . . .
C3 C 0.1691(4) 0.9573(3) 0.87791(16) 0.0612(9) Uani 1 1 d . . .
H3 H 0.1782 0.9170 0.9187 0.073 Uiso 1 1 calc R . .
C16 C 0.6437(4) 0.5849(3) 0.85480(17) 0.0665(9) Uani 1 1 d . . .
C12 C 0.0625(4) 1.0695(3) 0.88141(17) 0.0634(9) Uani 1 1 d . . .
H12 H 0.0131 1.0729 0.9220 0.076 Uiso 1 1 calc R . .
C11 C -0.0453(4) 1.0505(3) 0.83051(16) 0.0609(9) Uani 1 1 d . . .
C4 C 0.1017(4) 0.8688(3) 0.83013(19) 0.0772(12) Uani 1 1 d . . .
H4A H 0.1742 0.8452 0.7991 0.093 Uiso 1 1 calc R . .
H4B H 0.0653 0.7943 0.8504 0.093 Uiso 1 1 calc R . .
C7 C -0.1103(5) 0.9066(4) 0.75083(19) 0.0836(12) Uani 1 1 d . . .
H7 H -0.0953 0.8316 0.7304 0.100 Uiso 1 1 calc R . .
C10 C -0.1565(5) 1.1294(4) 0.8114(2) 0.0811(11) Uani 1 1 d . . .
H10 H -0.1728 1.2040 0.8321 0.097 Uiso 1 1 calc R . .
C8 C -0.2198(6) 0.9852(6) 0.7317(2) 0.0995(17) Uani 1 1 d . . .
H8 H -0.2793 0.9633 0.6982 0.119 Uiso 1 1 calc R . .
C9 C -0.2423(5) 1.0963(5) 0.7616(3) 0.0995(16) Uani 1 1 d . . .
H9 H -0.3164 1.1494 0.7480 0.119 Uiso 1 1 calc R . .
O6 O 0.6343(3) 0.9387(2) 0.96287(10) 0.0735(7) Uani 1 1 d . . .
C18 C 0.6300(5) 0.8198(4) 0.97806(19) 0.0774(11) Uani 1 1 d . . .
C19 C 0.6457(5) 1.0371(4) 1.01250(17) 0.0720(11) Uani 1 1 d . . .
O5 O 0.6305(5) 0.7774(3) 1.02907(13) 0.1260(14) Uani 1 1 d . . .
C21 C 0.6626(5) 0.4535(4) 0.8349(2) 0.0954(14) Uani 1 1 d . . .
H21A H 0.7631 0.4287 0.8412 0.143 Uiso 1 1 calc R . .
H21B H 0.6380 0.4458 0.7916 0.143 Uiso 1 1 calc R . .
H21C H 0.5989 0.4012 0.8591 0.143 Uiso 1 1 calc R . .
C20B C 0.6499(6) 1.1537(3) 0.9745(2) 0.1024(15) Uani 1 1 d . . .
H20A H 0.5594 1.1620 0.9517 0.154 Uiso 1 1 calc R . .
H20B H 0.7310 1.1499 0.9458 0.154 Uiso 1 1 calc R . .
H20C H 0.6621 1.2239 1.0015 0.154 Uiso 1 1 calc R . .
C20A C 0.5149(5) 1.0320(4) 1.0544(2) 0.1111(17) Uani 1 1 d . . .
H20D H 0.4266 1.0313 1.0297 0.167 Uiso 1 1 calc R . .
H20E H 0.5146 1.1034 1.0811 0.167 Uiso 1 1 calc R . .
H20F H 0.5193 0.9580 1.0792 0.167 Uiso 1 1 calc R . .
C20C C 0.7890(5) 1.0187(5) 1.0464(2) 0.1080(16) Uani 1 1 d . . .
H20G H 0.8088 1.0898 1.0720 0.162 Uiso 1 1 calc R . .
H20H H 0.8671 1.0084 1.0167 0.162 Uiso 1 1 calc R . .
H20I H 0.7825 0.9460 1.0721 0.162 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
O2 C1 1.356(4) . ?
O2 C12 1.466(4) . ?
O4 C15 1.191(4) . ?
O3 C13 1.357(4) . ?
O3 C14 1.430(4) . ?
C13 C2 1.316(5) . ?
N1 C18 1.394(4) . ?
N1 C15 1.406(4) . ?
N1 C14 1.451(4) . ?
C2 C1 1.461(5) . ?
C2 C3 1.485(5) . ?
O1 C1 1.197(4) . ?
C6 C11 1.376(5) . ?
C6 C7 1.380(5) . ?
C6 C4 1.497(5) . ?
C17 C16 1.327(5) . ?
C17 C14 1.493(5) . ?
C15 C16 1.484(5) . ?
C3 C4 1.529(5) . ?
C3 C12 1.550(5) . ?
C16 C21 1.489(5) . ?
C12 C11 1.480(5) . ?
C11 C10 1.381(5) . ?
C7 C8 1.368(6) . ?
C10 C9 1.370(6) . ?
C8 C9 1.374(7) . ?
O6 C18 1.324(4) . ?
O6 C19 1.507(4) . ?
C18 O5 1.186(4) . ?
C19 C20A 1.489(6) . ?
C19 C20B 1.499(5) . ?
C19 C20C 1.503(6) . ?

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 O2 C12 111.3(3) . . ?
C13 O3 C14 117.8(3) . . ?
C2 C13 O3 120.5(3) . . ?
C18 N1 C15 125.3(3) . . ?
C18 N1 C14 123.7(3) . . ?
C15 N1 C14 110.9(3) . . ?
C13 C2 C1 119.6(3) . . ?
C13 C2 C3 129.0(3) . . ?
C1 C2 C3 111.3(3) . . ?
C11 C6 C7 119.6(4) . . ?
C11 C6 C4 111.0(3) . . ?
C7 C6 C4 129.3(4) . . ?
C16 C17 C14 111.7(3) . . ?
O1 C1 O2 121.4(3) . . ?
O1 C1 C2 130.2(4) . . ?
O2 C1 C2 108.3(3) . . ?
O3 C14 N1 109.2(3) . . ?
O3 C14 C17 108.3(3) . . ?
N1 C14 C17 102.6(3) . . ?
O4 C15 N1 126.6(3) . . ?
O4 C15 C16 127.4(3) . . ?
N1 C15 C16 106.0(3) . . ?
C2 C3 C4 116.7(3) . . ?
C2 C3 C12 101.5(3) . . ?
C4 C3 C12 105.6(3) . . ?
C17 C16 C15 108.7(3) . . ?
C17 C16 C21 130.7(3) . . ?
C15 C16 C21 120.6(3) . . ?
O2 C12 C11 110.8(3) . . ?
O2 C12 C3 107.3(3) . . ?
C11 C12 C3 105.6(3) . . ?
C6 C11 C10 120.6(4) . . ?
C6 C11 C12 111.3(3) . . ?
C10 C11 C12 128.0(3) . . ?
C6 C4 C3 105.5(3) . . ?
C8 C7 C6 119.7(4) . . ?
C9 C10 C11 119.1(4) . . ?
C7 C8 C9 120.5(4) . . ?
C10 C9 C8 120.5(5) . . ?
C18 O6 C19 120.7(3) . . ?
O5 C18 O6 126.9(4) . . ?
O5 C18 N1 123.5(4) . . ?
O6 C18 N1 109.6(3) . . ?
C20A C19 C20B 112.4(4) . . ?
C20A C19 C20C 113.1(4) . . ?
C20B C19 C20C 110.6(4) . . ?
C20A C19 O6 110.2(3) . . ?
C20B C19 O6 101.9(3) . . ?
C20C C19 O6 107.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        66.58
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.033
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
