# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1482392'
_audit_update_record             
;
2016-05-28 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'methyl 1-((2R,3R)-4-methylene-5-oxo-3-phenyltetrahydrofuran-2-yl)-9H-pyrido[3,4-b]indole-3-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          477
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 N2 O4'
_chemical_formula_weight         398.40

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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   9.8351(6)
_cell_length_b                   19.0381(12)
_cell_length_c                   20.4995(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3838.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9804
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      25.23

_exptl_crystal_description       block
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      273(2)
_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            97825
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0930
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.063
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             3376
_reflns_number_gt                2682
_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0618P)²+5.8103P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3376
_refine_ls_number_parameters     343
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1646
_refine_ls_wR_factor_gt          0.1571
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.096
_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
C12 C 0.8285(3) 0.24705(16) 0.23172(14) 0.0358(7) Uani 1 1 d . . . . .
H12 H 0.760(3) 0.3193(12) 0.4512(11) 0.008(6) Uiso 1 1 d . . . . .
H13 H 0.647(3) 0.3342(16) 0.1830(17) 0.039(9) Uiso 1 1 d . . . . .
H17 H 0.457(3) 0.4328(15) 0.1368(15) 0.033(8) Uiso 1 1 d . . . . .
H16 H 0.291(3) 0.5238(14) 0.1360(14) 0.021(7) Uiso 1 1 d . . . . .
H8 H 0.705(3) 0.2438(16) 0.5630(15) 0.037(8) Uiso 1 1 d . . . . .
H11 H 0.462(3) 0.3197(17) 0.4398(17) 0.046(9) Uiso 1 1 d . . . . .
H2 H 1.059(3) 0.1927(16) 0.2026(16) 0.037(8) Uiso 1 1 d . . . . .
H15 H 0.214(3) 0.5671(17) 0.2220(15) 0.033(9) Uiso 1 1 d . . . . .
H10 H 0.411(3) 0.3002(12) 0.5915(16) 0.044(9) Uiso 1 1 d D . . . .
H4 H 0.440(4) 0.1980(18) 0.4138(18) 0.053(10) Uiso 1 1 d . . . . .
H7 H 0.742(4) 0.121(2) 0.5753(19) 0.063(11) Uiso 1 1 d . . . . .
H14 H 0.276(3) 0.5355(18) 0.3313(17) 0.046(9) Uiso 1 1 d . . . . .
H18 H 0.469(3) 0.4531(17) 0.3911(18) 0.045(9) Uiso 1 1 d . . . . .
H3 H 0.959(4) 0.126(2) 0.2149(19) 0.060(11) Uiso 1 1 d . . . . .
H5 H 0.470(4) 0.075(2) 0.430(2) 0.077(13) Uiso 1 1 d . . . . .
H6 H 0.632(4) 0.0387(19) 0.5100(17) 0.055(10) Uiso 1 1 d . . . . .
H9 H 0.455(3) 0.3878(18) 0.6122(18) 0.047(10) Uiso 1 1 d . . . . .
H1 H 1.072(4) 0.148(2) 0.274(2) 0.072(13) Uiso 1 1 d . . . . .
O3 O 0.9114(2) 0.21149(11) 0.26968(10) 0.0405(6) Uani 1 1 d . . . . .
O1 O 0.6757(2) 0.41512(10) 0.46002(10) 0.0403(6) Uani 1 1 d . . . . .
N2 N 0.7426(3) 0.29922(12) 0.33222(11) 0.0304(6) Uani 1 1 d . . . . .
N1 N 0.4755(3) 0.43525(13) 0.34899(12) 0.0331(6) Uani 1 1 d . . . . .
O2 O 0.6180(3) 0.47571(12) 0.54782(11) 0.0514(7) Uani 1 1 d . . . . .
C7 C 0.5640(3) 0.38269(14) 0.25962(14) 0.0303(7) Uani 1 1 d . . . . .
C1 C 0.4653(3) 0.43287(15) 0.23789(14) 0.0319(7) Uani 1 1 d . . . . .
C10 C 0.5690(3) 0.38570(14) 0.32863(13) 0.0288(7) Uani 1 1 d . . . . .
C9 C 0.7363(3) 0.29596(15) 0.26637(13) 0.0309(7) Uani 1 1 d . . . . .
C8 C 0.6503(3) 0.33588(16) 0.22868(15) 0.0339(7) Uani 1 1 d . . . . .
C19 C 0.5673(3) 0.23110(14) 0.48693(13) 0.0291(7) Uani 1 1 d . . . . .
C11 C 0.6597(3) 0.34316(14) 0.36324(13) 0.0296(7) Uani 1 1 d . . . . .
C6 C 0.4129(3) 0.46419(14) 0.29518(15) 0.0319(7) Uani 1 1 d . . . . .
C14 C 0.6697(3) 0.34216(14) 0.43674(14) 0.0312(7) Uani 1 1 d . . . . .
O4 O 0.8291(3) 0.24212(18) 0.17300(12) 0.0719(9) Uani 1 1 d . . . . .
C20 C 0.4991(3) 0.18191(17) 0.44951(15) 0.0382(8) Uani 1 1 d . . . . .
C5 C 0.3116(3) 0.51559(17) 0.29117(17) 0.0393(8) Uani 1 1 d . . . . .
C23 C 0.6777(4) 0.13648(18) 0.54357(16) 0.0423(8) Uani 1 1 d . . . . .
C15 C 0.5474(3) 0.30864(15) 0.47293(14) 0.0308(7) Uani 1 1 d . . . . .
C4 C 0.2674(4) 0.53495(18) 0.23100(18) 0.0439(8) Uani 1 1 d . . . . .
C24 C 0.6564(3) 0.20782(17) 0.53469(15) 0.0363(7) Uani 1 1 d . . . . .
C2 C 0.4179(3) 0.45396(17) 0.17696(16) 0.0368(7) Uani 1 1 d . . . . .
C16 C 0.5322(3) 0.35667(16) 0.53099(14) 0.0380(8) Uani 1 1 d . . . . .
C17 C 0.6094(4) 0.42172(16) 0.51682(14) 0.0378(8) Uani 1 1 d . . . . .
C3 C 0.3200(3) 0.50496(18) 0.17329(18) 0.0424(8) Uani 1 1 d . . . . .
C13 C 1.0062(4) 0.16601(19) 0.23615(19) 0.0466(9) Uani 1 1 d . . . . .
C18 C 0.4608(4) 0.3482(2) 0.58541(17) 0.0551(10) Uani 1 1 d D . . . .
C21 C 0.5197(4) 0.11064(18) 0.45928(18) 0.0480(9) Uani 1 1 d . . . . .
C22 C 0.6095(4) 0.08775(18) 0.50591(17) 0.0457(9) 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
C12 O4 1.207(4) . ?
C12 O3 1.315(4) . ?
C12 C9 1.482(4) . ?
O3 C13 1.446(4) . ?
O1 C17 1.340(4) . ?
O1 C14 1.470(3) . ?
N2 C11 1.330(4) . ?
N2 C9 1.353(4) . ?
N1 C6 1.378(4) . ?
N1 C10 1.382(4) . ?
O2 C17 1.211(4) . ?
C7 C8 1.385(4) . ?
C7 C10 1.417(4) . ?
C7 C1 1.433(4) . ?
C1 C2 1.392(4) . ?
C1 C6 1.415(4) . ?
C10 C11 1.398(4) . ?
C9 C8 1.374(4) . ?
C19 C20 1.384(4) . ?
C19 C24 1.387(4) . ?
C19 C15 1.517(4) . ?
C11 C14 1.510(4) . ?
C6 C5 1.398(4) . ?
C14 C15 1.551(4) . ?
C20 C21 1.386(5) . ?
C5 C4 1.359(5) . ?
C23 C22 1.381(5) . ?
C23 C24 1.386(5) . ?
C15 C16 1.508(4) . ?
C4 C3 1.412(5) . ?
C2 C3 1.370(5) . ?
C16 C18 1.328(5) . ?
C16 C17 1.481(5) . ?
C21 C22 1.373(5) . ?

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
O4 C12 O3 123.2(3) . . ?
O4 C12 C9 122.0(3) . . ?
O3 C12 C9 114.8(2) . . ?
C12 O3 C13 115.3(3) . . ?
C17 O1 C14 110.6(2) . . ?
C11 N2 C9 118.6(3) . . ?
C6 N1 C10 109.2(2) . . ?
C8 C7 C10 117.5(3) . . ?
C8 C7 C1 134.6(3) . . ?
C10 C7 C1 107.9(2) . . ?
C2 C1 C6 120.1(3) . . ?
C2 C1 C7 134.3(3) . . ?
C6 C1 C7 105.7(3) . . ?
N1 C10 C11 131.8(3) . . ?
N1 C10 C7 107.8(3) . . ?
C11 C10 C7 120.4(3) . . ?
N2 C9 C8 124.3(3) . . ?
N2 C9 C12 118.6(3) . . ?
C8 C9 C12 117.0(2) . . ?
C9 C8 C7 118.4(3) . . ?
C20 C19 C24 118.8(3) . . ?
C20 C19 C15 119.4(3) . . ?
C24 C19 C15 121.8(3) . . ?
N2 C11 C10 120.8(3) . . ?
N2 C11 C14 115.4(3) . . ?
C10 C11 C14 123.7(3) . . ?
N1 C6 C5 130.2(3) . . ?
N1 C6 C1 109.5(3) . . ?
C5 C6 C1 120.4(3) . . ?
O1 C14 C11 108.3(2) . . ?
O1 C14 C15 105.3(2) . . ?
C11 C14 C15 115.6(3) . . ?
C19 C20 C21 120.8(3) . . ?
C4 C5 C6 118.1(3) . . ?
C22 C23 C24 120.8(3) . . ?
C16 C15 C19 117.0(2) . . ?
C16 C15 C14 101.8(2) . . ?
C19 C15 C14 113.0(2) . . ?
C5 C4 C3 122.2(3) . . ?
C23 C24 C19 120.1(3) . . ?
C3 C2 C1 119.3(3) . . ?
C18 C16 C17 122.5(3) . . ?
C18 C16 C15 129.9(3) . . ?
C17 C16 C15 107.5(2) . . ?
O2 C17 O1 120.1(3) . . ?
O2 C17 C16 129.9(3) . . ?
O1 C17 C16 109.9(2) . . ?
C2 C3 C4 119.9(3) . . ?
C22 C21 C20 120.3(3) . . ?
C21 C22 C23 119.2(3) . . ?

_refine_diff_density_max         0.700
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.053

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method dichloromethane
