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_7249390
_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         'C14 H15 N O2'
_chemical_formula_sum            'C14 H15 N O2'
_chemical_formula_weight         229.27
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_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                 102.765(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.4613(3)
_cell_length_b                   7.7422(2)
_cell_length_c                   20.6904(4)
_cell_measurement_reflns_used    5502
_cell_measurement_temperature    278(1)
_cell_measurement_theta_max      78.8420
_cell_measurement_theta_min      4.3700
_cell_volume                     2415.52(9)
_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      278.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.950
_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    -50.00 -20.00   0.50    0.23    --  -91.75  45.00 -90.00   60
  2  \w    -72.00 -19.00   0.50    0.23    --  -91.75  61.00 -60.00  106
  3  \w    -72.00 -19.00   0.50    0.23    --  -91.75  61.00 -30.00  106
  4  \w    -50.00 -20.00   0.50    0.23    --  -91.75  45.00 -60.00   60
  5  \w    -50.00 -20.00   0.50    0.23    --  -91.75  45.00-120.00   60
  6  \w    -50.00 -20.00   0.50    0.23    --  -91.75  45.00  60.00   60
  7  \w    -50.00 -20.00   0.50    0.23    --  -91.75  45.00  90.00   60
  8  \w    -49.00 -20.00   0.50    0.23    --  -91.75  44.00 125.00   58
  9  \w    -50.00 -20.00   0.50    0.23    --  -91.75  45.00 150.00   60
 10  \w    -49.00  24.00   0.50    0.13    --  -47.65  44.00 125.00  146
 11  \w    -23.00  28.00   0.50    0.13    --  -47.65  19.00 -90.00  102
 12  \w   -119.00 -35.00   0.50    0.13    --  -47.65 -44.00 -25.00  168
 13  \w    -85.00 -22.00   0.50    0.23    --  -91.75 125.00 150.00  126
 14  \w   -164.00 -78.00   0.50    0.23    --  -91.75 -44.00 -25.00  172
 15  \w   -119.00 -25.00   0.50    0.13    --  -47.65 -77.00-120.00  188
 16  \w    -27.00  23.00   0.50    0.13    --   47.65 -19.00-150.00  100
 17  \w     40.00  72.00   0.50    0.23    --  111.36 -61.00-150.00   64
 18  \w     40.00  72.00   0.50    0.23    --  111.36 -61.00-120.00   64
 19  \w     40.00  72.00   0.50    0.23    --  111.36 -61.00-180.00   64
 20  \w     40.00  72.00   0.50    0.23    --  111.36 -61.00 -30.00   64
 21  \w     40.00  72.00   0.50    0.23    --  111.36 -61.00   0.00   64
 22  \w     40.00 115.00   0.50    0.23    --  111.36 -77.00  60.00  150
 23  \w    -24.00  49.00   0.50    0.13    --   47.65 -44.00 -25.00  146
 24  \w     33.00 108.00   0.50    0.13    --   47.65  57.00-180.00  150
 25  \w     99.00 178.00   0.50    0.23    --  111.36  45.00-150.00  158
 26  \w     35.00 120.00   0.50    0.13    --   47.65  44.00 125.00  170
 27  \w     99.00 178.00   0.50    0.23    --  111.36  44.00 125.00  158
;
_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  0.0292
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12062
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.993
_diffrn_reflns_theta_min         4.382
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.570
_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    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.00080(14)
_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   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0548P)^2^+0.5364P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1126
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1974
_reflns_number_total             2472
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4md00558a2.cif
_cod_data_source_block           c5721_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               7249390
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.893
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00D(H00D,H00E)
1.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00A(H00A), C00E(H00F), C00F(H00G)
1.c Idealised Me refined as rotating group:
 C00G(H00H,H00I,H00J), C00H(H00K,H00L,H00M)
;
_shelx_res_checksum              16618
_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
;