# 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_494MAR19
_database_code_depnum_ccdc_archive 'CCDC 1999796'
loop_
_audit_author_name
_audit_author_address
'Ruben Alfredo Toscano '
;Universidad Nacional Autonoma de Mexico
Mexico
;
_audit_update_record             
;
2020-04-28 deposited with the CCDC.	2021-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'(E)-2-(1-(4-Bromophenyl)-3-methoxy-3-oxoprop-1-en-2-yl)-1H-indole-3-carboxylic acid'
_chemical_name_common            ?
_chemical_melting_point          '158-160 \%C'
_chemical_formula_moiety         'C19 H14 Br N O4, C3 H6 O'
_chemical_formula_sum            'C22 H20 Br N O5'
_chemical_formula_weight         458.30

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'
Br Br -0.2901 2.4595 '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                   7.7741(4)
_cell_length_b                   11.2133(6)
_cell_length_c                   13.2379(7)
_cell_angle_alpha                71.4660(10)
_cell_angle_beta                 74.5380(10)
_cell_angle_gamma                81.4570(10)
_cell_volume                     1051.97(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7679
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      29.59

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.346
_exptl_crystal_size_min          0.296
_exptl_absorpt_coefficient_mu    1.986
_shelx_estimated_absorpt_T_min   0.497
_shelx_estimated_absorpt_T_max   0.591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5697
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            22459
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.725
_diffrn_reflns_theta_max         30.098
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6160
_reflns_number_gt                3767
_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       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (Hübschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0414P)²+0.2934P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6160
_refine_ls_number_parameters     272
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
Br1 Br 0.77972(4) 1.13355(3) 0.18974(3) 0.04840(12) Uani 1 1 d . . . . .
O1 O 0.4931(2) 0.42496(16) 0.13830(14) 0.0303(4) Uani 1 1 d D . . . .
H1 H 0.541(6) 0.417(4) 0.071(3) 0.118(17) Uiso 1 1 d D . . . .
O2 O 0.3500(2) 0.60041(15) 0.05287(13) 0.0313(4) Uani 1 1 d . . . . .
O3 O -0.0870(3) 0.8030(2) 0.06939(17) 0.0503(5) Uani 1 1 d . . . . .
O4 O -0.0565(2) 0.60790(18) 0.18042(14) 0.0394(4) Uani 1 1 d . . . . .
N1 N 0.1579(3) 0.64088(18) 0.36874(15) 0.0233(4) Uani 1 1 d . . . . .
H1A H 0.100(3) 0.693(2) 0.394(2) 0.028 Uiso 1 1 d . U . . .
C2 C 0.2000(3) 0.6505(2) 0.26030(17) 0.0217(5) Uani 1 1 d . . . . .
C3 C 0.3150(3) 0.5482(2) 0.24364(17) 0.0209(4) Uani 1 1 d . . . . .
C4 C 0.4481(3) 0.3612(2) 0.38561(19) 0.0260(5) Uani 1 1 d . . . . .
H4 H 0.519413 0.318161 0.335852 0.031 Uiso 1 1 calc R U . . .
C5 C 0.4432(3) 0.3157(2) 0.49544(19) 0.0298(5) Uani 1 1 d . . . . .
H5 H 0.512166 0.240208 0.521615 0.036 Uiso 1 1 calc R U . . .
C6 C 0.3386(3) 0.3781(2) 0.57000(19) 0.0290(5) Uani 1 1 d . . . . .
H6 H 0.338369 0.343942 0.645536 0.035 Uiso 1 1 calc R U . . .
C7 C 0.2372(3) 0.4867(2) 0.53645(18) 0.0260(5) Uani 1 1 d . . . . .
H7 H 0.165534 0.528572 0.587083 0.031 Uiso 1 1 calc R U . . .
C8 C 0.2430(3) 0.5337(2) 0.42495(17) 0.0216(5) Uani 1 1 d . . . . .
C9 C 0.3455(3) 0.4726(2) 0.34848(17) 0.0209(5) Uani 1 1 d . . . . .
C10 C 0.3881(3) 0.5249(2) 0.13856(18) 0.0217(5) Uani 1 1 d . . . . .
C11 C -0.0162(3) 0.7281(3) 0.1364(2) 0.0323(6) Uani 1 1 d . . . . .
C12 C 0.1246(3) 0.7565(2) 0.18145(18) 0.0244(5) Uani 1 1 d . . . . .
C13 C 0.1768(3) 0.8743(2) 0.14277(19) 0.0289(5) Uani 1 1 d . . . . .
H13 H 0.108901 0.931342 0.095420 0.035 Uiso 1 1 calc R U . . .
C14 C 0.3194(3) 0.9304(2) 0.16046(18) 0.0272(5) Uani 1 1 d . . . . .
C15 C 0.4389(3) 0.8666(2) 0.2249(2) 0.0320(6) Uani 1 1 d . . . . .
H15 H 0.426235 0.780035 0.264234 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5756(3) 0.9266(2) 0.2327(2) 0.0326(6) Uani 1 1 d . . . . .
H16 H 0.656372 0.881523 0.276635 0.039 Uiso 1 1 calc R U . . .
C17 C 0.5939(3) 1.0519(2) 0.1764(2) 0.0315(5) Uani 1 1 d . . . . .
C18 C 0.4802(4) 1.1178(2) 0.1113(2) 0.0462(7) Uani 1 1 d . . . . .
H18 H 0.495218 1.204108 0.071802 0.055 Uiso 1 1 calc R U . . .
C19 C 0.3433(4) 1.0577(2) 0.1038(2) 0.0420(7) Uani 1 1 d . . . . .
H19 H 0.263878 1.103641 0.059142 0.050 Uiso 1 1 calc R U . . .
C20 C -0.1875(4) 0.5700(3) 0.1394(3) 0.0560(9) Uani 1 1 d . . . . .
H20A H -0.298121 0.624012 0.149824 0.084 Uiso 1 1 calc R U . . .
H20B H -0.212150 0.482056 0.179410 0.084 Uiso 1 1 calc R U . . .
H20C H -0.141112 0.578326 0.061215 0.084 Uiso 1 1 calc R U . . .
O5 O 0.0366(4) 0.1757(3) 0.5274(3) 0.0943(10) Uani 1 1 d . . . . .
C21 C 0.1241(4) 0.1499(3) 0.4464(3) 0.0616(10) Uani 1 1 d . . . . .
C22 C 0.0938(6) 0.2185(5) 0.3371(4) 0.1022(16) Uani 1 1 d . . . . .
H22A H 0.193269 0.271536 0.294738 0.153 Uiso 1 1 calc R U . . .
H22B H -0.018272 0.271583 0.344548 0.153 Uiso 1 1 calc R U . . .
H22C H 0.086067 0.157972 0.299188 0.153 Uiso 1 1 calc R U . . .
C23 C 0.2667(5) 0.0475(3) 0.4531(3) 0.0748(11) Uani 1 1 d . . . . .
H23A H 0.239852 -0.016721 0.424784 0.112 Uiso 1 1 calc R U . . .
H23B H 0.273955 0.009468 0.529623 0.112 Uiso 1 1 calc R U . . .
H23C H 0.381277 0.081559 0.409260 0.112 Uiso 1 1 calc R U . . .


_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
Br1 C17 1.894(2) . ?
O1 C10 1.285(3) . ?
O1 H1 0.90(4) . ?
O2 C10 1.259(3) . ?
O3 C11 1.202(3) . ?
O4 C11 1.335(3) . ?
O4 C20 1.443(3) . ?
N1 C2 1.357(3) . ?
N1 C8 1.376(3) . ?
N1 H1A 0.79(3) . ?
C2 C3 1.384(3) . ?
C2 C12 1.475(3) . ?
C3 C9 1.438(3) . ?
C3 C10 1.446(3) . ?
C4 C5 1.371(3) . ?
C4 C9 1.400(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.364(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.406(3) . ?
C11 C12 1.492(3) . ?
C12 C13 1.338(3) . ?
C13 C14 1.456(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(3) . ?
C14 C19 1.399(3) . ?
C15 C16 1.381(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.373(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.370(4) . ?
C18 C19 1.382(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O5 C21 1.202(4) . ?
C21 C22 1.470(6) . ?
C21 C23 1.472(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C10 O1 H1 114(3) . . ?
C11 O4 C20 115.8(2) . . ?
C2 N1 C8 110.14(19) . . ?
C2 N1 H1A 123.8(19) . . ?
C8 N1 H1A 125.8(19) . . ?
N1 C2 C3 108.60(19) . . ?
N1 C2 C12 121.2(2) . . ?
C3 C2 C12 130.2(2) . . ?
C2 C3 C9 107.40(19) . . ?
C2 C3 C10 124.9(2) . . ?
C9 C3 C10 127.7(2) . . ?
C5 C4 C9 118.5(2) . . ?
C5 C4 H4 120.8 . . ?
C9 C4 H4 120.8 . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 121.5(2) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 117.2(2) . . ?
C6 C7 H7 121.4 . . ?
C8 C7 H7 121.4 . . ?
N1 C8 C7 129.6(2) . . ?
N1 C8 C9 107.81(19) . . ?
C7 C8 C9 122.6(2) . . ?
C4 C9 C8 118.8(2) . . ?
C4 C9 C3 135.2(2) . . ?
C8 C9 C3 106.04(19) . . ?
O2 C10 O1 122.9(2) . . ?
O2 C10 C3 120.7(2) . . ?
O1 C10 C3 116.5(2) . . ?
O3 C11 O4 123.3(2) . . ?
O3 C11 C12 125.0(2) . . ?
O4 C11 C12 111.6(2) . . ?
C13 C12 C2 125.9(2) . . ?
C13 C12 C11 117.1(2) . . ?
C2 C12 C11 117.0(2) . . ?
C12 C13 C14 131.4(2) . . ?
C12 C13 H13 114.3 . . ?
C14 C13 H13 114.3 . . ?
C15 C14 C19 117.4(2) . . ?
C15 C14 C13 125.5(2) . . ?
C19 C14 C13 117.1(2) . . ?
C16 C15 C14 121.3(2) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C17 C16 C15 119.6(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C16 121.0(2) . . ?
C18 C17 Br1 119.97(19) . . ?
C16 C17 Br1 119.07(19) . . ?
C17 C18 C19 119.4(2) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C14 121.4(2) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C21 C22 121.9(4) . . ?
O5 C21 C23 121.0(4) . . ?
C22 C21 C23 117.2(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C2 C3 0.0(2) . . . . ?
C8 N1 C2 C12 179.26(19) . . . . ?
N1 C2 C3 C9 -0.5(2) . . . . ?
C12 C2 C3 C9 -179.7(2) . . . . ?
N1 C2 C3 C10 179.4(2) . . . . ?
C12 C2 C3 C10 0.3(4) . . . . ?
C9 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C2 N1 C8 C7 -179.5(2) . . . . ?
C2 N1 C8 C9 0.5(2) . . . . ?
C6 C7 C8 N1 -178.9(2) . . . . ?
C6 C7 C8 C9 1.1(3) . . . . ?
C5 C4 C9 C8 0.5(3) . . . . ?
C5 C4 C9 C3 -179.9(2) . . . . ?
N1 C8 C9 C4 178.93(19) . . . . ?
C7 C8 C9 C4 -1.1(3) . . . . ?
N1 C8 C9 C3 -0.8(2) . . . . ?
C7 C8 C9 C3 179.2(2) . . . . ?
C2 C3 C9 C4 -178.8(2) . . . . ?
C10 C3 C9 C4 1.2(4) . . . . ?
C2 C3 C9 C8 0.8(2) . . . . ?
C10 C3 C9 C8 -179.1(2) . . . . ?
C2 C3 C10 O2 0.5(3) . . . . ?
C9 C3 C10 O2 -179.6(2) . . . . ?
C2 C3 C10 O1 180.0(2) . . . . ?
C9 C3 C10 O1 -0.1(3) . . . . ?
C20 O4 C11 O3 2.4(4) . . . . ?
C20 O4 C11 C12 -178.1(2) . . . . ?
N1 C2 C12 C13 76.6(3) . . . . ?
C3 C2 C12 C13 -104.4(3) . . . . ?
N1 C2 C12 C11 -106.8(2) . . . . ?
C3 C2 C12 C11 72.3(3) . . . . ?
O3 C11 C12 C13 -0.9(4) . . . . ?
O4 C11 C12 C13 179.6(2) . . . . ?
O3 C11 C12 C2 -177.8(2) . . . . ?
O4 C11 C12 C2 2.7(3) . . . . ?
C2 C12 C13 C14 3.1(4) . . . . ?
C11 C12 C13 C14 -173.5(2) . . . . ?
C12 C13 C14 C15 1.0(4) . . . . ?
C12 C13 C14 C19 177.7(3) . . . . ?
C19 C14 C15 C16 0.1(4) . . . . ?
C13 C14 C15 C16 176.9(2) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C15 C16 C17 C18 -1.0(4) . . . . ?
C15 C16 C17 Br1 179.05(19) . . . . ?
C16 C17 C18 C19 1.1(4) . . . . ?
Br1 C17 C18 C19 -179.0(2) . . . . ?
C17 C18 C19 C14 -0.6(5) . . . . ?
C15 C14 C19 C18 0.0(4) . . . . ?
C13 C14 C19 C18 -177.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.90(4) 1.69(4) 2.585(2) 175(4) 2_665 yes
N1 H1A O5 0.79(3) 2.07(3) 2.858(3) 174(3) 2_566 yes
C18 H18 O2 0.95 2.53 3.434(3) 159.0 2_675 yes

_refine_diff_density_max         0.416
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.072


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone/hexane'
_chemical_properties_physical    Air-sensitive,Light-sensitive
