#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:30:10 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178471 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/92/4029245.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4029245
loop_
_publ_author_name
'Bligh, Cavan M'
'Anzalone, Luigi'
'Jung, Young Chun'
'Zhang, Yuegang'
'Nugent, William A'
_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 ω and φ'
_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/[σ²(Fo²)+(0.0524P)²+0.0835P]
 where P=(Fo²+2Fc²)/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 > 2σ(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
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.925
_shelx_estimated_absorpt_t_max   0.961
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O2 O 0.75747(18) 0.8953(2) 0.30679(12) 0.0382(5) Uani 1 1 d . .
N5 N 0.5010(3) 0.8446(3) 0.33685(14) 0.0385(6) Uani 1 1 d . .
O5 O 0.7736(2) 1.1867(3) 0.38460(13) 0.0543(6) Uani 1 1 d . .
H5 H 0.7296 1.2489 0.4182 0.081 Uiso 1 1 calc R U
O1 O 0.1997(2) 1.0741(3) 0.57665(13) 0.0469(6) Uani 1 1 d . .
C1 C 0.6325(3) 0.8017(4) 0.28197(19) 0.0389(7) Uani 1 1 d . .
H1 H 0.6575 0.6896 0.2938 0.047 Uiso 1 1 calc R U
N1 N 0.0453(3) 1.0259(4) 0.45174(16) 0.0459(7) Uani 1 1 d . .
H1A H -0.0468 1.0169 0.4328 0.055 Uiso 1 1 calc R U
C2 C -0.0593(3) 1.0352(4) 0.60434(19) 0.0387(7) Uani 1 1 d . .
N2 N 0.1148(3) 1.0859(4) 0.30424(18) 0.0542(8) Uani 1 1 d . .
N4 N 0.3602(3) 0.8459(3) 0.46383(16) 0.0429(6) Uani 1 1 d . .
O4 O 0.6970(3) 0.7149(3) 0.13113(14) 0.0663(7) Uani 1 1 d . .
C3 C 0.2916(3) 0.9390(4) 0.39441(19) 0.0371(7) Uani 1 1 d . .
C4 C 0.0732(3) 1.0467(4) 0.54543(19) 0.0385(7) Uani 1 1 d . .
C5 C 0.7593(3) 1.0351(4) 0.24775(17) 0.0364(7) Uani 1 1 d . .
H5A H 0.8639 1.0574 0.2333 0.044 Uiso 1 1 calc R U
C6 C 0.3775(3) 0.9377(4) 0.31565(19) 0.0384(8) Uani 1 1 d . .
N3 N 0.3436(3) 1.0077(4) 0.23408(16) 0.0523(7) Uani 1 1 d . .
O3 O 0.7796(3) 0.9526(3) 0.08649(15) 0.0729(8) Uani 1 1 d . .
C7 C 0.1535(3) 1.0183(4) 0.38562(19) 0.0405(8) Uani 1 1 d . .
C8 C 0.6762(3) 0.9857(4) 0.15738(18) 0.0405(8) Uani 1 1 d . .
H8 H 0.6009 1.0647 0.1373 0.049 Uiso 1 1 calc R U
C9 C 0.2098(3) 1.0779(5) 0.2352(2) 0.0613(11) Uani 1 1 d . .
H9 H 0.1787 1.1282 0.1803 0.074 Uiso 1 1 calc R U
C10 C -0.1876(3) 0.9515(4) 0.5770(2) 0.0510(9) Uani 1 1 d . .
H10 H -0.1932 0.9027 0.5189 0.061 Uiso 1 1 calc R U
C11 C 0.6055(3) 0.8246(4) 0.17811(19) 0.0422(7) Uani 1 1 d . .
H11 H 0.4992 0.8182 0.1586 0.051 Uiso 1 1 calc R U
C12 C 0.4820(3) 0.7935(4) 0.42590(19) 0.0437(8) Uani 1 1 d . .
H12 H 0.5501 0.7268 0.4570 0.052 Uiso 1 1 calc R U
C13 C 0.6977(3) 1.1789(4) 0.29605(19) 0.0427(7) Uani 1 1 d . .
H13 H 0.5897 1.1659 0.3041 0.051 Uiso 1 1 calc R U
C14 C -0.0529(4) 1.1063(4) 0.6917(2) 0.0538(9) Uani 1 1 d . .
H14 H 0.0327 1.1618 0.7113 0.065 Uiso 1 1 calc R U
C15 C -0.2997(4) 1.0110(5) 0.7216(2) 0.0589(9) Uani 1 1 d . .
H15 H -0.3800 1.0023 0.7609 0.071 Uiso 1 1 calc R U
C16 C -0.1736(4) 1.0948(5) 0.7498(2) 0.0660(10) Uani 1 1 d . .
H16 H -0.1693 1.1439 0.8078 0.079 Uiso 1 1 calc R U
C17 C -0.3071(4) 0.9400(5) 0.6354(2) 0.0609(10) Uani 1 1 d . .
H17 H -0.3928 0.8841 0.6163 0.073 Uiso 1 1 calc R U
C18 C 0.7266(5) 1.3282(4) 0.2400(3) 0.0755(11) Uani 1 1 d . .
H18A H 0.6920 1.4196 0.2732 0.113 Uiso 1 1 calc R U
H18B H 0.6737 1.3212 0.1809 0.113 Uiso 1 1 calc R U
H18C H 0.8322 1.3382 0.2305 0.113 Uiso 1 1 calc R U
C19 C 0.7542(4) 0.7959(5) 0.0538(2) 0.0624(11) Uani 1 1 d . .
C20 C 0.6433(5) 0.7963(6) -0.0274(2) 0.0823(13) Uani 1 1 d . .
H20A H 0.5537 0.8509 -0.0103 0.123 Uiso 1 1 calc R U
H20B H 0.6190 0.6886 -0.0445 0.123 Uiso 1 1 calc R U
H20C H 0.6863 0.8496 -0.0792 0.123 Uiso 1 1 calc R U
C21 C 0.9037(5) 0.7231(9) 0.0299(3) 0.123(2) Uani 1 1 d . .
H21A H 0.9407 0.7740 -0.0245 0.185 Uiso 1 1 calc R U
H21B H 0.8908 0.6113 0.0181 0.185 Uiso 1 1 calc R U
H21C H 0.9742 0.7379 0.0811 0.185 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O2 C5 109.27(19)
C12 N5 C6 105.2(2)
C12 N5 C1 123.3(3)
C6 N5 C1 131.5(2)
O2 C1 N5 111.4(2)
O2 C1 C11 106.2(2)
N5 C1 C11 113.0(2)
C4 N1 C7 125.1(2)
C10 C2 C14 118.8(3)
C10 C2 C4 122.5(3)
C14 C2 C4 118.6(3)
C9 N2 C7 118.7(2)
C12 N4 C3 104.0(2)
C19 O4 C11 106.9(3)
C6 C3 N4 109.8(2)
C6 C3 C7 115.9(2)
N4 C3 C7 134.0(3)
O1 C4 N1 121.3(2)
O1 C4 C2 123.2(2)
N1 C4 C2 115.6(2)
O2 C5 C13 111.6(2)
O2 C5 C8 105.2(2)
C13 C5 C8 115.8(2)
N3 C6 N5 126.9(3)
N3 C6 C3 126.7(3)
N5 C6 C3 106.4(2)
C9 N3 C6 111.1(3)
C19 O3 C8 108.6(3)
N2 C7 N1 114.7(2)
N2 C7 C3 118.8(3)
N1 C7 C3 126.3(3)
O3 C8 C11 104.4(2)
O3 C8 C5 110.7(2)
C11 C8 C5 105.4(2)
N2 C9 N3 128.8(3)
C17 C10 C2 120.5(3)
O4 C11 C1 108.1(2)
O4 C11 C8 103.6(2)
C1 C11 C8 104.6(2)
N4 C12 N5 114.6(3)
O5 C13 C5 106.2(2)
O5 C13 C18 110.7(3)
C5 C13 C18 110.3(3)
C16 C14 C2 120.3(3)
C17 C15 C16 120.1(3)
C15 C16 C14 120.0(3)
C15 C17 C10 120.2(3)
O3 C19 O4 104.1(2)
O3 C19 C20 110.5(3)
O4 C19 C20 111.5(3)
O3 C19 C21 108.6(4)
O4 C19 C21 109.1(4)
C20 C19 C21 112.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C1 1.400(3)
O2 C5 1.449(3)
N5 C12 1.366(4)
N5 C6 1.376(4)
N5 C1 1.479(4)
O5 C13 1.423(3)
O1 C4 1.221(3)
C1 C11 1.517(4)
N1 C4 1.373(3)
N1 C7 1.378(4)
C2 C10 1.388(4)
C2 C14 1.390(4)
C2 C4 1.479(4)
N2 C9 1.327(4)
N2 C7 1.335(4)
N4 C12 1.307(4)
N4 C3 1.393(4)
O4 C19 1.413(4)
O4 C11 1.417(4)
C3 C6 1.388(4)
C3 C7 1.401(4)
C5 C13 1.506(4)
C5 C8 1.531(4)
C6 N3 1.337(4)
N3 C9 1.331(4)
O3 C19 1.413(5)
O3 C8 1.424(4)
C8 C11 1.525(4)
C10 C17 1.380(4)
C13 C18 1.516(5)
C14 C16 1.387(5)
C15 C17 1.375(5)
C15 C16 1.375(6)
C19 C20 1.504(5)
C19 C21 1.515(6)
