# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mb-va-vb-f-1-ds-s
_database_code_depnum_ccdc_archive 'CCDC 1941934'
loop_
_audit_author_name
_audit_author_address
'Vishal Agarwal'
;Pondicherry University
India
;
_audit_update_record             
;
2019-07-21 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_EXPT005_mb-va-vb-f-1-ds-s   
;
PROBLEM: _exptl_crystal_description is missing
RESPONSE: Block
;
# Added during the CSD deposition process: Sunday 21 July 2019 07:42 AM
# end Validation Reply Form

_audit_creation_date             2019-07-13
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            Tetrahydrochromeno[4,3-b]pyrrole
_chemical_name_systematic        
'dimethyl (E)-3-styryl-1,2,3,9b-tetrahydrochromeno[4,3-b]pyrrole-2,3a(4H)-dicarboxylate'
_chemical_formula_moiety         'C23 H23 N O5'
_chemical_formula_sum            'C7 H0 N16 O6'
_chemical_formula_weight         404.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H20 O5 N1'
_chemical_oxdiff_usercomment     'COLOURLESS BLOCK, 298K, 0.42 0.34 0.26'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   12.2643(9)
_cell_length_b                   7.5844(6)
_cell_length_c                   21.7321(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.637(7)
_cell_angle_gamma                90.00
_cell_volume                     2011.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3172
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0856
_cell_measurement_theta_min      3.1560
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11384
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.15
_diffrn_reflns_theta_min         3.16
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.9752
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -86.00   -1.00   1.0000   40.0500
omega____ theta____ kappa____ phi______ frames
    -      -16.8710  -57.0000  -90.0000 85

#__ type_ start__ end____ width___ exp.time_
  2 omega  -83.00    2.00   1.0000   40.0500
omega____ theta____ kappa____ phi______ frames
    -      -16.8710  -57.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
  3 omega  -11.00   19.00   1.0000   40.0500
omega____ theta____ kappa____ phi______ frames
    -      -16.8710  -99.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00   63.00   1.0000   40.0500
omega____ theta____ kappa____ phi______ frames
    -       19.5272  178.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega  -38.00   22.00   1.0000   40.0500
omega____ theta____ kappa____ phi______ frames
    -      -16.8710   57.0000   30.0000 60
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0242130000
_diffrn_orient_matrix_UB_12      0.0135805000
_diffrn_orient_matrix_UB_13      -0.0279382000
_diffrn_orient_matrix_UB_21      0.0519457000
_diffrn_orient_matrix_UB_22      0.0104409000
_diffrn_orient_matrix_UB_23      0.0170386000
_diffrn_orient_matrix_UB_31      0.0094158000
_diffrn_orient_matrix_UB_32      -0.0919947000
_diffrn_orient_matrix_UB_33      -0.0022145000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2904
_reflns_number_total             4689
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0085(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4689
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0677P)²+0.6927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1819
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
O1 O 0.73665(15) 0.5798(2) 0.56567(8) 0.0504(5) Uani 1 1 d . . .
O2 O 0.98589(15) 1.3556(2) 0.60169(9) 0.0563(5) Uani 1 1 d . . .
O3 O 0.74729(15) 0.8192(3) 0.70891(8) 0.0596(6) Uani 1 1 d . . .
O4 O 0.59432(15) 0.8641(3) 0.64734(9) 0.0740(7) Uani 1 1 d . . .
O5 O 0.99714(18) 1.2120(3) 0.51257(9) 0.0721(6) Uani 1 1 d . . .
N6 N 0.78804(18) 1.0709(3) 0.51684(9) 0.0441(5) Uani 1 1 d . . .
H6 H 0.834(2) 0.997(4) 0.4991(12) 0.053 Uiso 1 1 d . . .
C2 C 0.76830(17) 0.8808(3) 0.60466(10) 0.0354(5) Uani 1 1 d . . .
C3 C 0.85842(18) 1.0225(3) 0.62493(10) 0.0380(5) Uani 1 1 d . . .
H3 H 0.8390 1.0795 0.6628 0.046 Uiso 1 1 calc R . .
C4 C 0.97373(18) 0.9540(3) 0.63637(10) 0.0391(5) Uani 1 1 d . . .
H4 H 1.0071 0.9109 0.6028 0.047 Uiso 1 1 calc R . .
C5 C 1.0300(2) 0.9515(3) 0.69100(11) 0.0450(6) Uani 1 1 d . . .
H5 H 0.9930 0.9891 0.7240 0.054 Uiso 1 1 calc R . .
C6 C 0.66081(19) 0.8170(3) 0.50014(11) 0.0429(6) Uani 1 1 d . . .
C1 C 0.81850(19) 0.7032(3) 0.58979(11) 0.0425(6) Uani 1 1 d . . .
H1A H 0.8710 0.7206 0.5598 0.051 Uiso 1 1 calc R . .
H1B H 0.8575 0.6551 0.6271 0.051 Uiso 1 1 calc R . .
C7 C 0.70815(19) 0.9560(3) 0.54434(10) 0.0397(5) Uani 1 1 d . . .
H7 H 0.6478 1.0303 0.5556 0.048 Uiso 1 1 calc R . .
C8 C 0.8434(2) 1.1605(3) 0.57074(10) 0.0403(5) Uani 1 1 d . . .
H8 H 0.7948 1.2541 0.5830 0.048 Uiso 1 1 calc R . .
C9 C 1.14456(19) 0.8965(3) 0.70654(11) 0.0426(6) Uani 1 1 d . . .
C10 C 0.69170(19) 0.8547(3) 0.65474(11) 0.0415(6) Uani 1 1 d . . .
C11 C 0.6762(2) 0.6382(3) 0.51244(11) 0.0457(6) Uani 1 1 d . . .
C12 C 0.9489(2) 1.2440(3) 0.55706(11) 0.0453(6) Uani 1 1 d . . .
C13 C 0.5973(2) 0.8646(4) 0.44602(11) 0.0529(7) Uani 1 1 d . . .
H13 H 0.5864 0.9834 0.4367 0.064 Uiso 1 1 calc R . .
C14 C 1.1863(2) 0.8846(4) 0.76812(12) 0.0525(7) Uani 1 1 d . . .
H14 H 1.1407 0.9081 0.7989 0.063 Uiso 1 1 calc R . .
C15 C 1.2160(2) 0.8608(4) 0.66157(12) 0.0525(7) Uani 1 1 d . . .
H15 H 1.1906 0.8688 0.6199 0.063 Uiso 1 1 calc R . .
C16 C 0.6848(3) 0.7980(5) 0.76145(12) 0.0709(9) Uani 1 1 d . . .
H16A H 0.6378 0.6971 0.7551 0.106 Uiso 1 1 calc R . .
H16B H 0.6411 0.9015 0.7659 0.106 Uiso 1 1 calc R . .
H16C H 0.7339 0.7815 0.7982 0.106 Uiso 1 1 calc R . .
C17 C 0.6288(2) 0.5106(4) 0.47222(14) 0.0600(7) Uani 1 1 d . . .
H17 H 0.6394 0.3915 0.4810 0.072 Uiso 1 1 calc R . .
C18 C 1.3614(2) 0.8026(5) 0.73977(16) 0.0722(9) Uani 1 1 d . . .
H18 H 1.4338 0.7699 0.7510 0.087 Uiso 1 1 calc R . .
C19 C 1.3231(2) 0.8142(4) 0.67829(14) 0.0645(8) Uani 1 1 d . . .
H19 H 1.3696 0.7906 0.6480 0.077 Uiso 1 1 calc R . .
C1A C 1.2936(2) 0.8388(5) 0.78453(14) 0.0680(9) Uani 1 1 d . . .
H1AA H 1.3201 0.8325 0.8261 0.082 Uiso 1 1 calc R . .
C1B C 0.5501(2) 0.7388(5) 0.40588(13) 0.0657(8) Uani 1 1 d . . .
H1BA H 0.5077 0.7729 0.3700 0.079 Uiso 1 1 calc R . .
C1C C 0.5661(3) 0.5624(5) 0.41925(15) 0.0691(9) Uani 1 1 d . . .
H1C H 0.5342 0.4776 0.3923 0.083 Uiso 1 1 calc R . .
C1D C 1.0925(3) 1.4339(5) 0.59635(17) 0.0776(10) Uani 1 1 d . . .
H1DA H 1.0890 1.5073 0.5602 0.116 Uiso 1 1 calc R . .
H1DB H 1.1456 1.3423 0.5929 0.116 Uiso 1 1 calc R . .
H1DC H 1.1136 1.5039 0.6324 0.116 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
O1 C1 1.433(3) . ?
O1 C11 1.384(3) . ?
O2 C12 1.333(3) . ?
O2 C1D 1.451(3) . ?
O3 C10 1.329(3) . ?
O3 C16 1.446(3) . ?
O4 C10 1.192(3) . ?
O5 C12 1.206(3) . ?
N6 H6 0.90(3) . ?
N6 C7 1.480(3) . ?
N6 C8 1.462(3) . ?
C2 C3 1.574(3) . ?
C2 C1 1.529(3) . ?
C2 C7 1.549(3) . ?
C2 C10 1.519(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.504(3) . ?
C3 C8 1.573(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.314(3) . ?
C5 H5 0.9300 . ?
C5 C9 1.472(3) . ?
C6 C7 1.504(3) . ?
C6 C11 1.392(3) . ?
C6 C13 1.393(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C7 H7 0.9800 . ?
C8 H8 0.9800 . ?
C8 C12 1.497(3) . ?
C9 C14 1.388(3) . ?
C9 C15 1.401(3) . ?
C11 C17 1.392(4) . ?
C13 H13 0.9300 . ?
C13 C1B 1.381(4) . ?
C14 H14 0.9300 . ?
C14 C1A 1.373(4) . ?
C15 H15 0.9300 . ?
C15 C19 1.374(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9300 . ?
C17 C1C 1.377(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(4) . ?
C18 C1A 1.369(4) . ?
C19 H19 0.9300 . ?
C1A H1AA 0.9300 . ?
C1B H1BA 0.9300 . ?
C1B C1C 1.379(5) . ?
C1C H1C 0.9300 . ?
C1D H1DA 0.9600 . ?
C1D H1DB 0.9600 . ?
C1D H1DC 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
C11 O1 C1 113.30(18) . . ?
C12 O2 C1D 116.5(2) . . ?
C10 O3 C16 117.2(2) . . ?
C7 N6 H6 105.8(17) . . ?
C8 N6 H6 111.8(17) . . ?
C8 N6 C7 102.93(17) . . ?
C1 C2 C3 112.01(18) . . ?
C1 C2 C7 108.31(18) . . ?
C7 C2 C3 104.37(18) . . ?
C10 C2 C3 110.80(18) . . ?
C10 C2 C1 109.09(19) . . ?
C10 C2 C7 112.20(18) . . ?
C2 C3 H3 108.4 . . ?
C4 C3 C2 115.68(19) . . ?
C4 C3 H3 108.4 . . ?
C4 C3 C8 113.14(18) . . ?
C8 C3 C2 102.56(17) . . ?
C8 C3 H3 108.4 . . ?
C3 C4 H4 118.1 . . ?
C5 C4 C3 123.8(2) . . ?
C5 C4 H4 118.1 . . ?
C4 C5 H5 116.0 . . ?
C4 C5 C9 128.1(2) . . ?
C9 C5 H5 116.0 . . ?
C11 C6 C7 121.6(2) . . ?
C11 C6 C13 118.0(2) . . ?
C13 C6 C7 120.4(2) . . ?
O1 C1 C2 111.73(18) . . ?
O1 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
N6 C7 C2 106.23(18) . . ?
N6 C7 C6 112.59(18) . . ?
N6 C7 H7 108.0 . . ?
C2 C7 H7 108.0 . . ?
C6 C7 C2 113.82(19) . . ?
C6 C7 H7 108.0 . . ?
N6 C8 C3 107.54(18) . . ?
N6 C8 H8 107.9 . . ?
N6 C8 C12 112.32(19) . . ?
C3 C8 H8 107.9 . . ?
C12 C8 C3 112.95(19) . . ?
C12 C8 H8 107.9 . . ?
C14 C9 C5 119.5(2) . . ?
C14 C9 C15 117.6(2) . . ?
C15 C9 C5 122.8(2) . . ?
O3 C10 C2 111.20(19) . . ?
O4 C10 O3 123.5(2) . . ?
O4 C10 C2 125.3(2) . . ?
O1 C11 C6 121.6(2) . . ?
O1 C11 C17 117.3(2) . . ?
C6 C11 C17 121.1(3) . . ?
O2 C12 C8 111.3(2) . . ?
O5 C12 O2 123.6(2) . . ?
O5 C12 C8 125.1(2) . . ?
C6 C13 H13 119.4 . . ?
C1B C13 C6 121.3(3) . . ?
C1B C13 H13 119.4 . . ?
C9 C14 H14 119.3 . . ?
C1A C14 C9 121.3(3) . . ?
C1A C14 H14 119.3 . . ?
C9 C15 H15 119.6 . . ?
C19 C15 C9 120.8(3) . . ?
C19 C15 H15 119.6 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C17 H17 120.3 . . ?
C1C C17 C11 119.4(3) . . ?
C1C C17 H17 120.3 . . ?
C19 C18 H18 119.9 . . ?
C1A C18 H18 119.9 . . ?
C1A C18 C19 120.2(3) . . ?
C15 C19 C18 120.0(3) . . ?
C15 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C14 C1A H1AA 120.0 . . ?
C18 C1A C14 120.0(3) . . ?
C18 C1A H1AA 120.0 . . ?
C13 C1B H1BA 120.2 . . ?
C1C C1B C13 119.7(3) . . ?
C1C C1B H1BA 120.2 . . ?
C17 C1C C1B 120.6(3) . . ?
C17 C1C H1C 119.7 . . ?
C1B C1C H1C 119.7 . . ?
O2 C1D H1DA 109.5 . . ?
O2 C1D H1DB 109.5 . . ?
O2 C1D H1DC 109.5 . . ?
H1DA C1D H1DB 109.5 . . ?
H1DA C1D H1DC 109.5 . . ?
H1DB C1D H1DC 109.5 . . ?

_exptl_crystal_colour            Colorless
_exptl_crystal_description       Block
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM and DMF'
