# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 1911463'
loop_
_audit_author_name
_audit_author_address
'Sk Shamim Islam   '
;Indian Institute of Technology Kanpur
India
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1-(3,4,5-trimethoxyphenethyl)-1H-pyrrole-2-carboxylic acid'
_chemical_name_common            Peyonine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H38 N2 O10'
_chemical_formula_weight         610.64

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.2273(5)
_cell_length_b                   10.1947(6)
_cell_length_c                   10.5388(7)
_cell_angle_alpha                90.940(2)
_cell_angle_beta                 96.739(2)
_cell_angle_gamma                101.524(2)
_cell_volume                     754.96(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2687
_cell_measurement_theta_min      4.1
_cell_measurement_theta_max      25

_exptl_crystal_description       needle-like
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.6745
_exptl_absorpt_correction_T_max  0.7212
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Advance diffractometer'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9135
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.083
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.025
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2654
_reflns_number_gt                1975
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0403P)²+0.2617P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2654
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
C17 C 0.2026(3) 0.9125(2) -0.01974(19) 0.0255(5) Uani 1 1 d . . . . .
H17A H 0.1334 0.9713 0.0174 0.038 Uiso 1 1 calc R U . . .
H17B H 0.2637 0.9558 -0.0884 0.038 Uiso 1 1 calc R U . . .
H17C H 0.1163 0.8315 -0.0521 0.038 Uiso 1 1 calc R U . . .
O5 O 0.34281(19) 0.88097(14) 0.07522(12) 0.0234(3) Uani 1 1 d . . . . .
O4 O 0.63627(19) 0.85753(13) 0.24375(12) 0.0245(4) Uani 1 1 d . . . . .
O1 O 0.81121(18) 0.54770(13) -0.45362(12) 0.0234(3) Uani 1 1 d . . . . .
O3 O 0.86611(19) 0.69007(14) 0.19928(13) 0.0256(4) Uani 1 1 d . . . . .
N N 0.7098(2) 0.78468(15) -0.34091(14) 0.0174(4) Uani 1 1 d . . . . .
O2 O 1.10380(19) 0.67036(16) -0.45751(15) 0.0329(4) Uani 1 1 d . . . . .
C9 C 0.7263(3) 0.70098(19) 0.10191(17) 0.0182(4) Uani 1 1 d . . . . .
C8 C 0.7042(3) 0.63757(19) -0.01777(18) 0.0196(4) Uani 1 1 d . . . . .
H8 H 0.7887 0.5843 -0.0367 0.023 Uiso 1 1 calc R U . . .
C6 C 0.4307(3) 0.73195(19) -0.08036(17) 0.0188(4) Uani 1 1 d . . . . .
H6 H 0.3297 0.7406 -0.1408 0.023 Uiso 1 1 calc R U . . .
C5 C 0.4544(3) 0.79806(18) 0.03851(18) 0.0176(4) Uani 1 1 d . . . . .
C4 C 0.6036(3) 0.78268(19) 0.13050(17) 0.0184(4) Uani 1 1 d . . . . .
C7 C 0.5570(3) 0.65293(18) -0.10933(17) 0.0176(4) Uani 1 1 d . . . . .
C10 C 0.5345(3) 0.5851(2) -0.24012(18) 0.0210(5) Uani 1 1 d . . . . .
H10A H 0.4155 0.5199 -0.2519 0.025 Uiso 1 1 calc R U . . .
H10B H 0.6368 0.5369 -0.2442 0.025 Uiso 1 1 calc R U . . .
C15 C 0.8855(3) 0.7744(2) -0.37670(17) 0.0183(4) Uani 1 1 d . . . . .
C14 C 1.0054(3) 0.8987(2) -0.35306(19) 0.0243(5) Uani 1 1 d . . . . .
H14 H 1.1318 0.9208 -0.3683 0.029 Uiso 1 1 calc R U . . .
C11 C 0.5362(3) 0.68119(19) -0.34902(17) 0.0186(4) Uani 1 1 d . . . . .
H11A H 0.5217 0.6304 -0.4294 0.022 Uiso 1 1 calc R U . . .
H11B H 0.4279 0.7241 -0.3492 0.022 Uiso 1 1 calc R U . . .
C16 C 0.9261(3) 0.6551(2) -0.43150(17) 0.0196(5) Uani 1 1 d . . . . .
C3 C 0.9932(3) 0.6047(2) 0.1757(2) 0.0293(5) Uani 1 1 d . . . . .
H3A H 1.0836 0.6055 0.2503 0.044 Uiso 1 1 calc R U . . .
H3B H 0.9224 0.5151 0.1563 0.044 Uiso 1 1 calc R U . . .
H3C H 1.0592 0.6361 0.1047 0.044 Uiso 1 1 calc R U . . .
C12 C 0.7232(3) 0.9117(2) -0.29584(18) 0.0220(5) Uani 1 1 d . . . . .
H12 H 0.6254 0.9448 -0.2650 0.026 Uiso 1 1 calc R U . . .
C13 C 0.9032(3) 0.9841(2) -0.30259(19) 0.0261(5) Uani 1 1 d . . . . .
H13 H 0.9483 1.0739 -0.2779 0.031 Uiso 1 1 calc R U . . .
C2 C 0.5370(3) 0.7959(2) 0.34273(19) 0.0351(6) Uani 1 1 d . . . . .
H2A H 0.5669 0.8539 0.4182 0.053 Uiso 1 1 calc R U . . .
H2B H 0.4026 0.7799 0.3159 0.053 Uiso 1 1 calc R U . . .
H2C H 0.5744 0.7124 0.3611 0.053 Uiso 1 1 calc R U . . .
H2 H 1.126(3) 0.593(3) -0.493(2) 0.053(8) Uiso 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
C17 O5 1.426(2) . ?
O5 C5 1.360(2) . ?
O4 C4 1.376(2) . ?
O4 C2 1.419(2) . ?
O1 C16 1.235(2) . ?
O3 C9 1.375(2) . ?
O3 C3 1.424(2) . ?
N C12 1.353(2) . ?
N C15 1.389(2) . ?
N C11 1.462(2) . ?
O2 C16 1.324(2) . ?
C9 C8 1.385(3) . ?
C9 C4 1.386(3) . ?
C8 C7 1.385(3) . ?
C6 C5 1.389(3) . ?
C6 C7 1.388(3) . ?
C5 C4 1.398(3) . ?
C7 C10 1.509(3) . ?
C10 C11 1.521(3) . ?
C15 C14 1.385(3) . ?
C15 C16 1.435(3) . ?
C14 C13 1.386(3) . ?
C12 C13 1.372(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
C5 O5 C17 117.23(14) . . ?
C4 O4 C2 114.37(15) . . ?
C9 O3 C3 117.33(15) . . ?
C12 N C15 107.85(16) . . ?
C12 N C11 123.85(16) . . ?
C15 N C11 128.29(15) . . ?
O3 C9 C8 124.53(17) . . ?
O3 C9 C4 115.15(16) . . ?
C8 C9 C4 120.32(17) . . ?
C7 C8 C9 120.43(18) . . ?
C5 C6 C7 120.29(18) . . ?
O5 C5 C6 125.05(17) . . ?
O5 C5 C4 115.01(16) . . ?
C6 C5 C4 119.94(17) . . ?
O4 C4 C9 120.80(17) . . ?
O4 C4 C5 119.55(17) . . ?
C9 C4 C5 119.42(17) . . ?
C8 C7 C6 119.58(17) . . ?
C8 C7 C10 120.33(17) . . ?
C6 C7 C10 120.08(17) . . ?
C7 C10 C11 113.77(16) . . ?
C14 C15 N 107.54(17) . . ?
C14 C15 C16 128.15(18) . . ?
N C15 C16 124.29(17) . . ?
C13 C14 C15 107.75(18) . . ?
N C11 C10 113.61(15) . . ?
O1 C16 O2 121.84(18) . . ?
O1 C16 C15 125.21(17) . . ?
O2 C16 C15 112.96(17) . . ?
N C12 C13 109.54(17) . . ?
C12 C13 C14 107.31(18) . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.058

