# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_150115a_0m
_database_code_depnum_ccdc_archive 'CCDC 1418405'
_audit_update_record             
;
2015-08-12 deposited with the CCDC.
2015-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'5,8-Dimethoxy-1,6b-dimethyl-1a,6b-dihydro-1H- benzofuro[2,3-b]indole'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 N O3'
_chemical_formula_weight         297.34

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                   11.5236(15)
_cell_length_b                   7.0451(9)
_cell_length_c                   19.746(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.5650(10)
_cell_angle_gamma                90.00
_cell_volume                     1551.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6407
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.34

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9863
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            12642
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         27.38
_reflns_number_total             3517
_reflns_number_gt                2770
_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)+(0.0577P)²+0.2991P] 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         3517
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
C1 C 0.85242(19) 0.1957(3) 0.58507(10) 0.0778(5) Uani 1 1 d . . .
H1A H 0.8335 0.0693 0.5676 0.117 Uiso 1 1 calc R . .
H1B H 0.8139 0.2203 0.6220 0.117 Uiso 1 1 calc R . .
H1C H 0.9376 0.2079 0.6028 0.117 Uiso 1 1 calc R . .
C2 C 0.85772(12) 0.3378(2) 0.47035(8) 0.0513(3) Uani 1 1 d . . .
C3 C 0.96392(14) 0.2653(2) 0.46081(10) 0.0642(4) Uani 1 1 d . . .
H3 H 1.0135 0.1916 0.4954 0.077 Uiso 1 1 calc R . .
C4 C 0.99550(13) 0.3040(2) 0.39886(10) 0.0646(5) Uani 1 1 d . . .
H4 H 1.0667 0.2553 0.3919 0.078 Uiso 1 1 calc R . .
C5 C 0.92310(13) 0.4132(2) 0.34764(9) 0.0554(4) Uani 1 1 d . . .
C6 C 0.81554(12) 0.4858(2) 0.35728(8) 0.0475(3) Uani 1 1 d . . .
H6 H 0.7664 0.5607 0.3230 0.057 Uiso 1 1 calc R . .
C7 C 0.78361(11) 0.44495(18) 0.41797(7) 0.0435(3) Uani 1 1 d . . .
C8 C 0.67234(12) 0.50421(19) 0.44079(7) 0.0434(3) Uani 1 1 d . . .
C9 C 0.55970(11) 0.41626(18) 0.39593(7) 0.0403(3) Uani 1 1 d . . .
C10 C 0.48955(11) 0.46898(19) 0.33089(7) 0.0427(3) Uani 1 1 d . . .
H10 H 0.5074 0.5772 0.3085 0.051 Uiso 1 1 calc R . .
C11 C 0.39187(12) 0.3557(2) 0.30011(7) 0.0441(3) Uani 1 1 d . . .
C12 C 0.36607(12) 0.1940(2) 0.33385(7) 0.0486(3) Uani 1 1 d . . .
H12 H 0.3005 0.1196 0.3124 0.058 Uiso 1 1 calc R . .
C13 C 0.43582(13) 0.1419(2) 0.39856(8) 0.0493(3) Uani 1 1 d . . .
H13 H 0.4186 0.0336 0.4211 0.059 Uiso 1 1 calc R . .
C14 C 0.53213(12) 0.25608(19) 0.42863(7) 0.0442(3) Uani 1 1 d . . .
C15 C 0.68887(14) 0.3876(2) 0.50971(7) 0.0508(3) Uani 1 1 d . . .
H15 H 0.6693 0.4650 0.5466 0.061 Uiso 1 1 calc R . .
C16 C 1.06122(17) 0.4145(3) 0.27434(13) 0.0872(6) Uani 1 1 d . . .
H16A H 1.1218 0.4733 0.3106 0.131 Uiso 1 1 calc R . .
H16B H 1.0667 0.4617 0.2296 0.131 Uiso 1 1 calc R . .
H16C H 1.0728 0.2795 0.2760 0.131 Uiso 1 1 calc R . .
C17 C 0.32013(16) 0.5694(2) 0.20523(9) 0.0633(4) Uani 1 1 d . . .
H17A H 0.3129 0.6665 0.2380 0.095 Uiso 1 1 calc R . .
H17B H 0.2554 0.5808 0.1639 0.095 Uiso 1 1 calc R . .
H17C H 0.3951 0.5835 0.1929 0.095 Uiso 1 1 calc R . .
C18 C 0.66621(14) 0.7190(2) 0.45002(8) 0.0542(4) Uani 1 1 d . . .
H18A H 0.6641 0.7807 0.4064 0.081 Uiso 1 1 calc R . .
H18B H 0.7355 0.7606 0.4849 0.081 Uiso 1 1 calc R . .
H18C H 0.5951 0.7505 0.4646 0.081 Uiso 1 1 calc R . .
N1 N 0.81068(12) 0.3304(2) 0.52913(7) 0.0590(3) Uani 1 1 d . . .
O1 O 0.60835(9) 0.22337(15) 0.49296(5) 0.0568(3) Uani 1 1 d . . .
O2 O 0.94625(11) 0.4575(2) 0.28433(7) 0.0764(4) Uani 1 1 d . . .
O3 O 0.31559(10) 0.38959(16) 0.23572(5) 0.0584(3) 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 N1 1.444(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.382(2) . ?
C2 C7 1.3873(19) . ?
C2 N1 1.400(2) . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(2) . ?
C4 H4 0.9300 . ?
C5 O2 1.378(2) . ?
C5 C6 1.397(2) . ?
C6 C7 1.370(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.5206(18) . ?
C8 C9 1.5084(19) . ?
C8 C18 1.5277(19) . ?
C8 C15 1.5596(19) . ?
C9 C14 1.3764(18) . ?
C9 C10 1.3851(18) . ?
C10 C11 1.3889(19) . ?
C10 H10 0.9300 . ?
C11 O3 1.3726(16) . ?
C11 C12 1.3891(19) . ?
C12 C13 1.377(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(2) . ?
C13 H13 0.9300 . ?
C14 O1 1.3701(16) . ?
C15 N1 1.417(2) . ?
C15 O1 1.4682(18) . ?
C15 H15 0.9800 . ?
C16 O2 1.420(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O3 1.4094(18) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 119.98(15) . . ?
C3 C2 N1 129.79(15) . . ?
C7 C2 N1 110.13(13) . . ?
C2 C3 C4 118.99(15) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 120.91(14) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 O2 125.07(14) . . ?
C4 C5 C6 120.00(15) . . ?
O2 C5 C6 114.92(14) . . ?
C7 C6 C5 119.01(14) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C2 121.07(13) . . ?
C6 C7 C8 129.33(12) . . ?
C2 C7 C8 109.59(12) . . ?
C9 C8 C7 112.23(11) . . ?
C9 C8 C18 114.72(11) . . ?
C7 C8 C18 112.02(11) . . ?
C9 C8 C15 101.21(11) . . ?
C7 C8 C15 100.78(11) . . ?
C18 C8 C15 114.62(12) . . ?
C14 C9 C10 120.33(12) . . ?
C14 C9 C8 109.11(11) . . ?
C10 C9 C8 130.53(12) . . ?
C9 C10 C11 118.13(12) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
O3 C11 C10 124.41(12) . . ?
O3 C11 C12 114.99(12) . . ?
C10 C11 C12 120.59(12) . . ?
C13 C12 C11 121.22(13) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 117.56(13) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 H13 121.2 . . ?
O1 C14 C9 113.77(12) . . ?
O1 C14 C13 124.06(12) . . ?
C9 C14 C13 122.16(13) . . ?
N1 C15 O1 111.32(12) . . ?
N1 C15 C8 106.33(12) . . ?
O1 C15 C8 106.67(11) . . ?
N1 C15 H15 110.8 . . ?
O1 C15 H15 110.8 . . ?
C8 C15 H15 110.8 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 C18 H18A 109.5 . . ?
C8 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C8 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 N1 C15 109.19(11) . . ?
C2 N1 C1 122.32(15) . . ?
C15 N1 C1 120.70(15) . . ?
C14 O1 C15 107.32(10) . . ?
C5 O2 C16 118.54(16) . . ?
C11 O3 C17 117.91(12) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.38
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.034
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: petroleum ether and ethyl acetate'
