Preparation of both c5' epimers of 5'-C-methyladenosine: reagent control trumps substrate control.
Bligh, Cavan M; Anzalone, Luigi; Jung, Young Chun; Zhang, Yuegang; Nugent, William A; The Journal of organic chemistry 79 (2014) 3238–3243; doi:10.1021/jo500089t

data_4029245
_publ_section_title
;
 Preparation of both c5' epimers of 5'-C-methyladenosine: reagent control
 trumps substrate control.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3238
_journal_page_last               3243
_journal_paper_doi               10.1021/jo500089t
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C21 H23 N5 O5'
_chemical_formula_weight         425.44
_chemical_name_systematic
;
VRT-1205044
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 91.907(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9140(1)
_cell_length_b                   8.3961(1)
_cell_length_c                   14.3759(2)
_cell_measurement_temperature    296(2)
_cell_volume                     1075.34(2)
_computing_cell_refinement       'Bruker APEX'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker APEX'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker APEX'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.599
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_device_type  'Bruker APEX II CCD diifractometer'
_diffrn_measurement_method       'oscillation photos around \w and \f'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.599
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4692
_diffrn_reflns_point_group_measured_fraction_full 0.436
_diffrn_reflns_point_group_measured_fraction_max 0.665
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         53.504
_diffrn_reflns_theta_min         3.076
_diffrn_source                   'seal tube'
_exptl_absorpt_coefficient_mu    0.798
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       Prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 439 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.10(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         1698
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+0.0835P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0708
_reflns_Friedel_coverage         0.356
_reflns_Friedel_fraction_full    0.248
_reflns_Friedel_fraction_max     0.382
_reflns_number_gt                1688
_reflns_number_total             1698
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo500089t_si_002.cif
_cod_data_source_block           VRT-1205044
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029245.cif.
;
_cod_database_code               4029245
_shelx_estimated_absorpt_t_min   0.925
_shelx_estimated_absorpt_t_max   0.961