Careful Navigation of the Crystallographic Landscape of MK-8970: A Racemic Acetal Carbonate Prodrug of Raltegravir
Tsou, Nancy; Shultz, C. Scott; Andreani, Teresa; Ball, Richard G.; Brunskill, Andrew; Balsells, Jaume; Cohen, Ryan D.; DaSilva, Jimmy; Li, Jing; Reamer, Robert A.; de Lera Ruiz, Manuel; Variankaval, Narayan; Varsolona, Richard J.; Yasuda, Nobuyoshi; York, Gregory; Organic Process Research & Development 19 (2015) 1882–; doi:10.1021/acs.oprd.5b00129

data_1520611
_publ_section_title
;
 Careful Navigation of the Crystallographic Landscape of MK-8970:
 A&#x00A0;Racemic Acetal Carbonate Prodrug of Raltegravir
;
_journal_issue                   12
_journal_name_full               'Organic Process Research &amp; Development'
_journal_page_first              1882
_journal_paper_doi               10.1021/acs.oprd.5b00129
_journal_volume                  19
_journal_year                    2015
_chemical_formula_moiety         'C22 H23 F N6 O5'
_chemical_formula_sum            'C22 H23 F N6 O5'
_chemical_formula_weight         470.46
_chemical_name_systematic
; 
(Z)-N-(2-(4-((4-fluorobenzyl)imino)-2,7-dimethyl-8-oxo-7,8-dihydro-4H-[1,3
dioxino[5,4-d]pyrimidin-6-yl)propan-2-yl)-5-methyl-1,3,4-oxadiazole-2-carboxamide 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 114.4961(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8135(4)
_cell_length_b                   13.3386(4)
_cell_length_c                   14.0876(4)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.73
_cell_measurement_theta_min      3.52
_cell_volume                     2362.04(12)
_computing_cell_refinement       'SAINT V8.34A'
_computing_data_collection       'SAINT V8.34A'
_computing_data_reduction        'SAINT V8.34A'
_computing_molecular_graphics    'Mercury 3.5.1'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20507
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.496
_diffrn_reflns_theta_min         3.516
_diffrn_source                   'sealed-tube X-ray generator'
_exptl_absorpt_coefficient_mu    0.855
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       'square plate'
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0509P)^2^+1.1675P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1090
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3496
_reflns_number_total             4149
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            op5b00129_si_003.cif
_cod_data_source_block           mdj070_abs
_cod_depositor_comments
'Adding full bibliography for 1520611--1520613.cif.'
_cod_database_code               1520611
_shelx_estimated_absorpt_t_min   0.919
_shelx_estimated_absorpt_t_max   0.983
_shelxl_version_number           2014-3
_shelx_res_checksum              43006
_shelx_hkl_checksum              60976