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_1520612
_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_absolute_configuration rmad
_chemical_formula_sum            'C25 H29 F N6 O8'
_chemical_formula_weight         560.54
_chemical_name_systematic
; 
(S)-ethyl (1-((4-((4-fluorobenzyl)carbamoyl)-1-methyl-2-(2-(5-methyl-1,3,4-
oxadiazole-2-carboxamido)propan-2-yl)-6-oxo-1,6-dihydropyrimidin-5-yl)
oxy)ethyl) 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4933(18)
_cell_length_b                   11.2461(19)
_cell_length_c                   24.486(4)
_cell_measurement_reflns_used    4082
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.5869
_cell_measurement_theta_min      3.6101
_cell_volume                     2614.2(8)
_computing_cell_refinement       'SAINT V7.68A'
_computing_data_collection       'SAINT V7.68A'
_computing_data_reduction        'SAINT V7.68A'
_computing_molecular_graphics    'Mercury 3.5.1'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10650
_diffrn_reflns_theta_full        66.51
_diffrn_reflns_theta_max         66.51
_diffrn_reflns_theta_min         3.61
_diffrn_source                   'sealed-tube X-ray generator'
_exptl_absorpt_coefficient_mu    0.9539
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003);
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         4366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0399P)^2^+0.1783P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0773
_reflns_number_gt                3937
_reflns_number_total             4366
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            op5b00129_si_001.cif
_cod_data_source_block           mdh062
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1520611--1520613.cif.
;
_cod_database_code               1520612