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_7249392
_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         'C16 H19 N O2'
_chemical_formula_sum            'C16 H19 N O2'
_chemical_formula_weight         257.32
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 94.209(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.12310(10)
_cell_length_b                   9.1098(2)
_cell_length_c                   19.3288(3)
_cell_measurement_reflns_used    6723
_cell_measurement_temperature    266.5(3)
_cell_measurement_theta_max      76.8350
_cell_measurement_theta_min      4.5520
_cell_volume                     1426.47(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      266.15
_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    -26.00  23.00   0.50    0.10    --   47.90 -19.00   0.00   98
  2  \w    -26.00  23.00   0.50    0.10    --   47.90 -19.00 -30.00   98
  3  \w    -26.00  23.00   0.50    0.10    --   47.90 -19.00 -60.00   98
  4  \w    105.00 178.00   0.50    0.20    --  111.36  94.00 103.00  146
  5  \w     40.00  72.00   0.50    0.20    --  111.36 -61.00  60.00   64
  6  \w     40.00  72.00   0.50    0.20    --  111.36 -61.00 120.00   64
  7  \w     40.00  72.00   0.50    0.20    --  111.36 -61.00 150.00   64
  8  \w     41.00  72.00   0.50    0.20    --  111.36 -61.00  30.00   62
  9  \w     40.00  72.00   0.50    0.20    --  111.36 -61.00   0.00   64
 10  \w     40.00  71.00   0.50    0.20    --  111.36 -61.00 -90.00   62
 11  \w     40.00  72.00   0.50    0.20    --  111.36 -61.00-120.00   64
 12  \w     40.00  65.00   0.50    0.20    --  111.36 -61.00-150.00   50
 13  \w     41.00  70.00   0.50    0.20    --  111.36 -61.00-180.00   58
 14  \w    -13.00  79.00   0.50    0.10    --   47.90 -94.00  -7.00  184
 15  \w     42.00 111.00   0.50    0.20    --  111.36-125.00  90.00  138
 16  \w     40.00 105.00   0.50    0.20    --  111.36 -94.00  -7.00  130
 17  \w    -78.00  25.00   0.50    0.10    --  -47.90  94.00 103.00  206
 18  \w    -80.00 -19.00   0.50    0.20    --  -91.75  94.00 103.00  122
 19  \w    -85.00 -22.00   0.50    0.20    --  -91.75 125.00  30.00  126
 20  \w    -72.00 -19.00   0.50    0.20    --  -91.75  61.00 -90.00  106
 21  \w    -72.00 -19.00   0.50    0.20    --  -91.75  61.00-180.00  106
 22  \w    -50.00 -20.00   0.50    0.20    --  -91.75  45.00-180.00   60
 23  \w    -50.00 -20.00   0.50    0.20    --  -91.75  45.00-120.00   60
 24  \w    -23.00  28.00   0.50    0.10    --  -47.90  19.00-150.00  102
 25  \w    -23.00  28.00   0.50    0.10    --  -47.90  19.00-180.00  102
 26  \w    -50.00 -20.00   0.50    0.20    --  -91.75  45.00 -30.00   60
 27  \w    -50.00 -20.00   0.50    0.20    --  -91.75  45.00  30.00   60
 28  \w    -50.00 -20.00   0.50    0.20    --  -91.75  45.00  60.00   60
 29  \w   -163.00 -83.00   0.50    0.20    --  -91.75 -94.00  -7.00  160
;
_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  0.0270
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14058
_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         78.645
_diffrn_reflns_theta_min         4.588
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.412
_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    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.0035(6)
_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   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0582P)^2^+0.1637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1330
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2357
_reflns_number_total             2929
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4md00558a2.cif
_cod_data_source_block           c5724_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               7249392
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.775
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C00E(H00E), C00G(H00G)
1.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C009(H009), C00C(H00C), C00D(H00D)
1.c Idealised Me refined as rotating group:
 C00F(H00A,H00B,H00F), C00H(H00H,H00I,H00J), C00I(H00K,H00L,H00M), C00J(H00N,
 H00O,H00P)
;
_shelx_res_checksum              65344
_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
;