Stereo- and regio-selective synthesis of 3′-C-substituted-(N)-methanocarba adenosines as potential anticancer agents
Naik, Siddhi D.; Chandra, Girish; Sahu, Pramod K.; Kim, Hong-Rae; Qu, Shuhao; Yoon, Ji-seong; Jeong, Lak Shin; Organic Chemistry Frontiers 3 (2016) 1472–; doi:10.1039/C6QO00358C

data_1553498
_publ_section_title
;
 Stereo- and regio-selective synthesis of
 3&#x2032;-C-substituted-(N)-methanocarba adenosines as potential
 anticancer agents
;
_journal_issue                   11
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1472
_journal_paper_doi               10.1039/C6QO00358C
_journal_volume                  3
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C14 H15 N5 O3, H2 O'
_chemical_formula_sum            'C14 H17 N5 O4'
_chemical_formula_weight         319.32
_chemical_name_systematic        'Triple 3c'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-07-12 deposited with the CCDC.
2016-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.51038(10)
_cell_length_b                   17.3551(2)
_cell_length_c                   23.2172(4)
_cell_measurement_reflns_used    15729
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      76.3580
_cell_measurement_theta_min      4.5560
_cell_volume                     3026.21(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_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   -116.00 -17.00   1.00    6.05    --  -41.24 -38.00  30.00   99
  2  \w   -116.00 -17.00   1.00    6.05    --  -41.24 -38.00 -60.00   99
  3  \w     23.00  97.00   1.00    6.05    --   41.24-125.00 -90.00   74
  4  \w     23.00  97.00   1.00    6.05    --   41.24-125.00-180.00   74
  5  \w     84.00 178.00   1.00   19.32    --  112.00  30.00  90.00   94
  6  \w     84.00 178.00   1.00   19.32    --  112.00  30.00 150.00   94
  7  \w    100.00 178.00   1.00   19.32    --  112.00 111.00   0.00   78
  8  \w    100.00 178.00   1.00   19.32    --  112.00 111.00 -30.00   78
  9  \w     36.00 145.00   1.00   19.32    --  112.00 -77.00  60.00  109
 10  \w     29.00 109.00   1.00   19.32    --  112.00 -94.00 -30.00   80
 11  \w     29.00 109.00   1.00   19.32    --  112.00 -94.00  30.00   80
 12  \w     29.00 109.00   1.00   19.32    --  112.00 -94.00 -90.00   80
 13  \w     86.00 178.00   1.00   19.32    --  112.00  45.00 -60.00   92
 14  \w     57.00 151.00   1.00   19.32    --  112.00 178.00  90.00   94
 15  \w   -117.00 -53.00   1.00    6.05    --  -41.24 -77.00 150.00   64
 16  \w   -116.00 -17.00   1.00    6.05    --  -41.24 -38.00-180.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2006207000
_diffrn_orient_matrix_UB_12      0.0173377000
_diffrn_orient_matrix_UB_13      0.0048446000
_diffrn_orient_matrix_UB_21      0.0207491000
_diffrn_orient_matrix_UB_22      -0.0122176000
_diffrn_orient_matrix_UB_23      -0.0653848000
_diffrn_orient_matrix_UB_31      -0.0371918000
_diffrn_orient_matrix_UB_32      0.0862068000
_diffrn_orient_matrix_UB_33      -0.0102294000
_diffrn_radiation_collimation    '0.2 mm sinlge-pinhole'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            25009
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.548
_diffrn_reflns_theta_min         3.808
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2559 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         6304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0264
_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^)+(0.0408P)^2^+0.3928P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0680
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                6059
_reflns_number_total             6304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00358c2.cif
_cod_data_source_block           exp_258
_cod_database_code               1553498
_chemical_oxdiff_formula         C14H15N5O3
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Free rotating group:
 O006(H00A), O008(H00C)
2.b Ternary CH refined with riding coordinates:
 C1'(H1'), C2'(H2'A), C6'(H6'), C1'A(H1'A), C2'A(H2'C), C6'A(H6'A)
2.c Secondary CH2 refined with riding coordinates:
 C5'(H5'A,H5'B), C7'(H7'A,H7'B), C5'A(H5'D,H5'E), C7'A(H7'C,H7'D)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C2A(H2A), C8A(H8A)
2.e X=CH2 refined with riding coordinates:
 N6A(H6AA,H6AB)
2.f Idealised tetrahedral OH refined as rotating group:
 O2'(H2'), O3'(H3'), O5'(H5'), O2'A(H2'B), O5'A(H5'C)
2.g :
 C3"'(H3"'), C1(H1)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-04-07
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.486
_oxdiff_exptl_absorpt_empirical_full_min 0.764