Total syntheses and antiproliferative activities of prenostodione and its analogues.
Ramos-Orea, Aldahir; Ramírez-Apan, Teresa; Chávez-Santos, Rosa María; Aguayo-Ortiz, Rodrigo; Espitia, Clara; Silva Miranda, Mayra; Torres-Ochoa, Rubén O; Martínez, Roberto; Organic & biomolecular chemistry 19 (2021) 8272–8280; doi:10.1039/d1ob00897h

data_7158273
_publ_section_title
;
 Total syntheses and antiproliferative activities of prenostodione and its
 analogues.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8272
_journal_page_last               8280
_journal_paper_doi               10.1039/d1ob00897h
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C19 H14 Br N O4, C3 H6 O'
_chemical_formula_sum            'C22 H20 Br N O5'
_chemical_formula_weight         458.30
_chemical_melting_point          432.1(10)
_chemical_name_systematic
'(E)-2-(1-(4-Bromophenyl)-3-methoxy-3-oxoprop-1-en-2-yl)-1H-indole-3-carboxylic acid'
_chemical_properties_physical    Air-sensitive,Light-sensitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-04-28 deposited with the CCDC.	2021-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                71.4660(10)
_cell_angle_beta                 74.5380(10)
_cell_angle_gamma                81.4570(10)
_cell_formula_units_Z            2
_cell_length_a                   7.7741(4)
_cell_length_b                   11.2133(6)
_cell_length_c                   13.2379(7)
_cell_measurement_reflns_used    7679
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.59
_cell_measurement_theta_min      2.73
_cell_volume                     1051.97(10)
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_collection       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2014)'
_computing_molecular_graphics    'SHELXLe (H\"ubschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 52.0833
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker D8 Venture \k geometry diffractometer 208039-1'
_diffrn_measurement_method       '\f and \w-scans'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22459
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.098
_diffrn_reflns_theta_min         2.725
_diffrn_source                   'micro-focus X-ray source'
_exptl_absorpt_coefficient_mu    1.986
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone/hexane'
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.346
_exptl_crystal_size_min          0.296
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         6160
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+0.2934P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3767
_reflns_number_total             6160
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00897h2.cif
_cod_data_source_block           494MAR19
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '158-160 \%C' was changed
to '432.1(10)' -- it was converted from degrees Celsius (C) to
kelvins (K), the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158273.cif.
;
_cod_database_code               7158273
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.497
_shelx_estimated_absorpt_t_max   0.591
_shelx_res_checksum              42556