Generation and Capture of Naphthoquinonynes: A New Frontier in the Development of Trypanocidal Quinones via Aryne Chemistry
Figueroa, Laura P. R.; Carvalho, Renato; Almeida, Renata G.; Paz, Esther R. S.; Diogo, Emilay; Araujo, Maria Helena; de souza Borges, Warley; dos Santos Ramos, Victor Feliciano; Menna-Barreto, Rubem F. S.; Wood, James M.; Bower, John; da Silva Júnior, Eufrânio N.; RSC Medicinal Chemistry  (2024) –; doi:10.1039/D4MD00558A

data_7249391
_publ_section_title
;
 Generation and Capture of Naphthoquinonynes: A New Frontier in the
 Development of Trypanocidal Quinones via Aryne Chemistry
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D4MD00558A
_journal_year                    2024
_chemical_formula_moiety         'C22 H15 N O2'
_chemical_formula_sum            'C22 H15 N O2'
_chemical_formula_weight         325.35
_chemical_melting_point          ?
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2024-04-17
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-03 deposited with the CCDC.	2024-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   35.2203(12)
_cell_length_b                   20.9152(7)
_cell_length_c                   9.2515(3)
_cell_measurement_reflns_used    5732
_cell_measurement_temperature    271(4)
_cell_measurement_theta_max      75.0100
_cell_measurement_theta_min      4.8960
_cell_volume                     6815.0(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      271.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -69.00 -19.00   0.50    0.64    --  -91.75  59.00-155.00  100
  2  \w    -70.00  25.00   0.50    0.20    --  -47.90  77.00-120.00  190
  3  \w    -50.00 -20.00   0.50    0.64    --  -91.75  45.00 -60.00   60
  4  \w    -72.00 -19.00   0.50    0.64    --  -91.75  61.00  12.00  106
  5  \w    -50.00 -20.00   0.50    0.64    --  -91.75  45.00  60.00   60
  6  \w    -23.00  28.00   0.50    0.20    --  -47.90  19.00 150.00  102
  7  \w    -50.00 -20.00   0.50    0.64    --  -91.75  45.00 120.00   60
  8  \w   -161.00 -75.00   0.50    0.64    --  -91.75-122.00  -2.00  172
  9  \w   -163.00 -75.00   0.50    0.64    --  -91.75 -61.00-126.00  176
 10  \w     40.00 106.00   0.50    0.64    --  111.36 -95.00-180.00  132
 11  \w     40.00  72.00   0.50    0.64    --  111.36 -61.00 -90.00   64
 12  \w     40.00  72.00   0.50    0.64    --  111.36 -61.00   0.00   64
 13  \w    -26.00  23.00   0.50    0.20    --   47.90 -19.00-120.00   98
 14  \w     25.00 120.00   0.50    0.20    --   47.90  77.00   0.00  190
 15  \w     25.00  52.00   0.50    0.20    --   47.90  77.00 120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8924
_diffrn_reflns_point_group_measured_fraction_full 0.912
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         4.918
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.483
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2720
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.094
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 853 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.00021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         2825
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0503P)^2^+0.9998P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.1004
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.819
_reflns_Friedel_fraction_max     0.813
_reflns_number_gt                2429
_reflns_number_total             2825
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4md00558a2.cif
_cod_data_source_block           c5723_benzino_bg25
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               7249391
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.809
_olex2_refinement_description
;
;
_shelx_res_checksum              80604
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;