Synthesis and oxidation of 2-hydroxynevirapine, a metabolite of the HIV reverse transcriptase inhibitor nevirapine.
Antunes, Alexandra M. M.; Novais, David A.; Ferreira da Silva, J. L.; Santos, Pedro P.; Conceição Oliveira, M; Beland, Frederick A.; Matilde Marques, M.; Organic & biomolecular chemistry 9 (2011) 7822–7835; doi:10.1039/c1ob06052j

data_7152053
_publ_section_title
;
 Synthesis and oxidation of 2-hydroxynevirapine, a metabolite of the HIV
 reverse transcriptase inhibitor nevirapine.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7822
_journal_page_last               7835
_journal_paper_doi               10.1039/c1ob06052j
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C16.5 H17 N4 O3.5'
_chemical_formula_weight         327.34
_chemical_name_systematic
;
1'-cyclopropyl-4-methyl-1H,1'H-spiro[pyridine-2,2'-
pyrido[2,3-d]pyrimidine]-3,4',6(3'H)-trione
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.650(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.528(10)
_cell_length_b                   8.433(4)
_cell_length_c                   17.211(8)
_cell_measurement_reflns_used    2973
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.88
_cell_measurement_theta_min      3.57
_cell_volume                     3114(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1230
_diffrn_reflns_av_sigmaI/netI    0.1332
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13236
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_diffrn_reflns_theta_max         25.88
_diffrn_reflns_theta_min         3.57
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9950
_exptl_absorpt_correction_T_min  0.9782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0042(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.1389
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                1551
_reflns_number_total             2973
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob06052j.txt
_cod_data_source_block           aa23c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

2018-12-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C33 H34 N8 O7'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     654.68
_cod_database_code               7152053