#------------------------------------------------------------------------------
#$Date: 2020-02-27 02:20:20 +0200 (Thu, 27 Feb 2020) $
#$Revision: 248466 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/79/4037962.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_4037962
loop_
_publ_author_name
'Köllmann, Christoph'
'Sake, Svenja M.'
'Jones, Peter G.'
'Pietschmann, Thomas'
'Werz, Daniel B.'
_publ_section_title
;
 Protecting-Group-Mediated Diastereoselective Synthesis of C4'-Methylated
 Uridine Analogs and their Activity against the Human Respiratory
 Syncytial Virus.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03425
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H20 N2 O6'
_chemical_formula_weight         408.40
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 92.4786(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.99677(7)
_cell_length_b                   7.61343(8)
_cell_length_c                   20.4686(2)
_cell_measurement_reflns_used    42415
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.6420
_cell_measurement_theta_min      2.2350
_cell_volume                     933.640(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-2017
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyP'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            58257
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        75.000
_diffrn_reflns_theta_max         78.029
_diffrn_reflns_theta_min         4.324
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1790 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3967
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0338
_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)+(0.0606P)²+0.2145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0882
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3936
_reflns_number_total             3967
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03425_si_004.cif
_cod_data_source_block           koell5
_cod_original_cell_volume        933.641(17)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4037962
_shelx_shelxl_version_number     2017/1
_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   0.878
_shelx_estimated_absorpt_t_max   0.965
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3059(3) 0.5682(3) 0.15291(9) 0.0187(4) Uani 1 1 d . . . . .
H1 H 0.242399 0.446714 0.151281 0.022 Uiso 1 1 calc R U . . .
C2 C 0.3784(3) 0.6135(3) 0.22461(8) 0.0190(3) Uani 1 1 d . . . . .
H2 H 0.527538 0.672387 0.227599 0.023 Uiso 1 1 calc R U . . .
C3 C 0.1938(3) 0.7342(3) 0.24672(9) 0.0206(4) Uani 1 1 d . . . . .
H3 H 0.250667 0.828253 0.277211 0.025 Uiso 1 1 calc R U . . .
C4 C 0.0806(4) 0.8077(3) 0.18493(10) 0.0270(4) Uani 1 1 d . . . . .
H4 H -0.084760 0.805450 0.189435 0.032 Uiso 1 1 calc R U . . .
C5 C 0.1525(7) 0.9928(3) 0.17093(12) 0.0518(9) Uani 1 1 d . . . . .
H5A H 0.105550 1.025621 0.125592 0.062 Uiso 1 1 calc R U . . .
H5B H 0.082203 1.075428 0.201222 0.062 Uiso 1 1 calc R U . . .
C6 C 0.5397(4) 0.7392(3) 0.07868(11) 0.0285(4) Uani 1 1 d . . . . .
H6 H 0.452467 0.839085 0.088603 0.034 Uiso 1 1 calc R U . . .
C7 C 0.7074(4) 0.7586(3) 0.03794(12) 0.0296(5) Uani 1 1 d . . . . .
H7 H 0.737562 0.870593 0.019895 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8413(3) 0.6096(3) 0.02164(9) 0.0195(4) Uani 1 1 d . . . . .
C9 C 0.6096(4) 0.4318(3) 0.09346(10) 0.0249(4) Uani 1 1 d . . . . .
C10 C 0.1905(3) 0.4894(2) 0.30953(8) 0.0165(3) Uani 1 1 d . . . . .
C11 C 0.2729(3) 0.5641(2) 0.37566(9) 0.0187(4) Uani 1 1 d . . . . .
C12 C 0.1217(3) 0.5754(3) 0.42551(9) 0.0225(4) Uani 1 1 d . . . . .
H12 H -0.023485 0.526762 0.419066 0.027 Uiso 1 1 calc R U . . .
C13 C 0.1814(4) 0.6570(3) 0.48444(10) 0.0268(4) Uani 1 1 d . . . . .
H13 H 0.077472 0.663604 0.518102 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3934(4) 0.7290(3) 0.49407(10) 0.0287(4) Uani 1 1 d . . . . .
H14 H 0.433443 0.787395 0.533896 0.034 Uiso 1 1 calc R U . . .
C15 C 0.5456(4) 0.7154(3) 0.44554(10) 0.0268(4) Uani 1 1 d . . . . .
H15 H 0.691047 0.763323 0.452338 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4868(3) 0.6315(3) 0.38641(9) 0.0221(4) Uani 1 1 d . . . . .
H16 H 0.593262 0.620658 0.353592 0.027 Uiso 1 1 calc R U . . .
C17 C 0.0690(3) 0.3170(2) 0.31730(9) 0.0193(4) Uani 1 1 d . . . . .
C18 C 0.1748(4) 0.1848(3) 0.35399(10) 0.0260(4) Uani 1 1 d . . . . .
H18 H 0.320327 0.203426 0.372886 0.031 Uiso 1 1 calc R U . . .
C19 C 0.0676(5) 0.0260(3) 0.36290(12) 0.0380(6) Uani 1 1 d . . . . .
H19 H 0.139960 -0.064591 0.387690 0.046 Uiso 1 1 calc R U . . .
C20 C -0.1435(5) -0.0005(3) 0.33589(16) 0.0490(8) Uani 1 1 d . . . . .
H20 H -0.217104 -0.109176 0.342364 0.059 Uiso 1 1 calc R U . . .
C21 C -0.2492(4) 0.1299(4) 0.29941(18) 0.0485(7) Uani 1 1 d . . . . .
H21 H -0.394854 0.110565 0.280668 0.058 Uiso 1 1 calc R U . . .
C22 C -0.1425(3) 0.2899(3) 0.29004(13) 0.0309(5) Uani 1 1 d . . . . .
H22 H -0.215105 0.379956 0.265002 0.037 Uiso 1 1 calc R U . . .
O1 O 0.1384(2) 0.68887(19) 0.13295(6) 0.0216(3) Uani 1 1 d . . . . .
O2 O 0.3711(2) 0.46429(17) 0.26653(6) 0.0190(3) Uani 1 1 d . . . . .
O3 O 0.0477(2) 0.61374(18) 0.27729(6) 0.0186(3) Uani 1 1 d . . . . .
O4 O 0.3865(5) 1.0017(3) 0.17925(9) 0.0611(7) Uani 1 1 d . . . . .
H04 H 0.460(9) 1.083(9) 0.161(3) 0.103(18) Uiso 1 1 d . . . . .
O5 O 1.0002(2) 0.6134(2) -0.01431(6) 0.0229(3) Uani 1 1 d . . . . .
O6 O 0.5722(4) 0.2905(2) 0.11883(11) 0.0536(6) Uani 1 1 d . . . . .
N1 N 0.4890(3) 0.5804(2) 0.10669(7) 0.0195(3) Uani 1 1 d . . . . .
N2 N 0.7756(3) 0.4525(2) 0.04976(8) 0.0222(3) Uani 1 1 d . . . . .
H02 H 0.860(6) 0.361(5) 0.0404(17) 0.042(9) Uiso 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 108.18(14) . . ?
O1 C1 C2 107.25(15) . . ?
N1 C1 C2 113.86(14) . . ?
O2 C2 C3 105.10(14) . . ?
O2 C2 C1 112.19(15) . . ?
C3 C2 C1 103.75(15) . . ?
O3 C3 C4 109.93(16) . . ?
O3 C3 C2 102.11(15) . . ?
C4 C3 C2 106.24(15) . . ?
O1 C4 C5 111.41(17) . . ?
O1 C4 C3 105.63(16) . . ?
C5 C4 C3 112.5(2) . . ?
O4 C5 C4 108.3(2) . . ?
C7 C6 N1 122.68(19) . . ?
C6 C7 C8 119.93(19) . . ?
O5 C8 N2 120.57(18) . . ?
O5 C8 C7 125.14(19) . . ?
N2 C8 C7 114.28(16) . . ?
O6 C9 N2 121.95(19) . . ?
O6 C9 N1 122.25(19) . . ?
N2 C9 N1 115.80(17) . . ?
O3 C10 O2 105.04(13) . . ?
O3 C10 C17 110.09(14) . . ?
O2 C10 C17 109.15(14) . . ?
O3 C10 C11 109.16(14) . . ?
O2 C10 C11 111.59(14) . . ?
C17 C10 C11 111.60(15) . . ?
C16 C11 C12 119.05(17) . . ?
C16 C11 C10 122.52(17) . . ?
C12 C11 C10 118.29(16) . . ?
C13 C12 C11 120.69(18) . . ?
C12 C13 C14 119.92(19) . . ?
C15 C14 C13 119.79(18) . . ?
C14 C15 C16 120.42(19) . . ?
C11 C16 C15 120.08(18) . . ?
C22 C17 C18 120.01(19) . . ?
C22 C17 C10 121.72(18) . . ?
C18 C17 C10 118.27(17) . . ?
C19 C18 C17 119.9(2) . . ?
C20 C19 C18 120.0(2) . . ?
C19 C20 C21 120.4(2) . . ?
C20 C21 C22 120.0(2) . . ?
C17 C22 C21 119.6(2) . . ?
C1 O1 C4 112.59(14) . . ?
C2 O2 C10 107.82(13) . . ?
C10 O3 C3 105.20(13) . . ?
C9 N1 C6 120.80(16) . . ?
C9 N1 C1 118.94(15) . . ?
C6 N1 C1 120.24(16) . . ?
C9 N2 C8 126.36(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.409(2) . ?
C1 N1 1.483(2) . ?
C1 C2 1.551(2) . ?
C2 O2 1.425(2) . ?
C2 C3 1.523(3) . ?
C3 O3 1.431(2) . ?
C3 C4 1.516(3) . ?
C4 O1 1.450(2) . ?
C4 C5 1.505(3) . ?
C5 O4 1.408(5) . ?
C6 C7 1.342(3) . ?
C6 N1 1.378(3) . ?
C7 C8 1.437(3) . ?
C8 O5 1.229(2) . ?
C8 N2 1.392(2) . ?
C9 O6 1.220(3) . ?
C9 N2 1.376(3) . ?
C9 N1 1.376(3) . ?
C10 O3 1.420(2) . ?
C10 O2 1.437(2) . ?
C10 C17 1.513(3) . ?
C10 C11 1.531(2) . ?
C11 C16 1.390(3) . ?
C11 C12 1.397(3) . ?
C12 C13 1.390(3) . ?
C13 C14 1.391(3) . ?
C14 C15 1.382(3) . ?
C15 C16 1.400(3) . ?
C17 C22 1.379(3) . ?
C17 C18 1.392(3) . ?
C18 C19 1.385(3) . ?
C19 C20 1.374(5) . ?
C20 C21 1.380(5) . ?
C21 C22 1.393(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H04 O6 0.85(6) 1.94(7) 2.779(3) 169(6) 1_565 yes
N2 H02 O5 0.88(4) 2.14(4) 3.014(2) 168(3) 2_745 yes
C5 H5A O5 0.99 2.43 3.421(3) 178.1 2_655 yes
C6 H6 O4 0.95 2.28 3.040(3) 136.5 . yes
C7 H7 O5 0.95 2.43 3.268(3) 146.6 2_755 yes
C21 H21 O4 0.95 2.55 3.363(4) 144.3 1_445 yes
C22 H22 O2 0.95 2.56 3.222(2) 126.5 1_455 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 127.85(15) . . . . ?
N1 C1 C2 O2 -112.50(17) . . . . ?
O1 C1 C2 C3 14.93(19) . . . . ?
N1 C1 C2 C3 134.57(16) . . . . ?
O2 C2 C3 O3 -23.76(17) . . . . ?
C1 C2 C3 O3 94.19(16) . . . . ?
O2 C2 C3 C4 -138.95(16) . . . . ?
C1 C2 C3 C4 -21.0(2) . . . . ?
O3 C3 C4 O1 -89.97(18) . . . . ?
C2 C3 C4 O1 19.8(2) . . . . ?
O3 C3 C4 C5 148.3(2) . . . . ?
C2 C3 C4 C5 -102.0(2) . . . . ?
O1 C4 C5 O4 -72.6(2) . . . . ?
C3 C4 C5 O4 45.8(2) . . . . ?
N1 C6 C7 C8 0.4(4) . . . . ?
C6 C7 C8 O5 -178.9(2) . . . . ?
C6 C7 C8 N2 1.8(3) . . . . ?
O3 C10 C11 C16 -103.4(2) . . . . ?
O2 C10 C11 C16 12.2(2) . . . . ?
C17 C10 C11 C16 134.65(18) . . . . ?
O3 C10 C11 C12 72.2(2) . . . . ?
O2 C10 C11 C12 -172.18(16) . . . . ?
C17 C10 C11 C12 -49.8(2) . . . . ?
C16 C11 C12 C13 1.8(3) . . . . ?
C10 C11 C12 C13 -173.98(17) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 -1.5(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C12 C11 C16 C15 -2.5(3) . . . . ?
C10 C11 C16 C15 173.07(18) . . . . ?
C14 C15 C16 C11 1.2(3) . . . . ?
O3 C10 C17 C22 5.6(2) . . . . ?
O2 C10 C17 C22 -109.2(2) . . . . ?
C11 C10 C17 C22 127.0(2) . . . . ?
O3 C10 C17 C18 -173.34(16) . . . . ?
O2 C10 C17 C18 71.9(2) . . . . ?
C11 C10 C17 C18 -52.0(2) . . . . ?
C22 C17 C18 C19 0.2(3) . . . . ?
C10 C17 C18 C19 179.15(17) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C18 C19 C20 C21 0.5(4) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C18 C17 C22 C21 0.0(3) . . . . ?
C10 C17 C22 C21 -179.0(2) . . . . ?
C20 C21 C22 C17 0.1(4) . . . . ?
N1 C1 O1 C4 -126.05(16) . . . . ?
C2 C1 O1 C4 -2.8(2) . . . . ?
C5 C4 O1 C1 111.8(2) . . . . ?
C3 C4 O1 C1 -10.6(2) . . . . ?
C3 C2 O2 C10 1.82(17) . . . . ?
C1 C2 O2 C10 -110.27(16) . . . . ?
O3 C10 O2 C2 21.25(17) . . . . ?
C17 C10 O2 C2 139.28(15) . . . . ?
C11 C10 O2 C2 -96.90(16) . . . . ?
O2 C10 O3 C3 -37.22(17) . . . . ?
C17 C10 O3 C3 -154.61(15) . . . . ?
C11 C10 O3 C3 82.56(16) . . . . ?
C4 C3 O3 C10 149.72(15) . . . . ?
C2 C3 O3 C10 37.26(17) . . . . ?
O6 C9 N1 C6 178.1(2) . . . . ?
N2 C9 N1 C6 -1.9(3) . . . . ?
O6 C9 N1 C1 -0.5(3) . . . . ?
N2 C9 N1 C1 179.47(16) . . . . ?
C7 C6 N1 C9 -0.4(3) . . . . ?
C7 C6 N1 C1 178.2(2) . . . . ?
O1 C1 N1 C9 -147.66(17) . . . . ?
C2 C1 N1 C9 93.2(2) . . . . ?
O1 C1 N1 C6 33.7(2) . . . . ?
C2 C1 N1 C6 -85.4(2) . . . . ?
O6 C9 N2 C8 -175.4(2) . . . . ?
N1 C9 N2 C8 4.6(3) . . . . ?
O5 C8 N2 C9 176.16(18) . . . . ?
C7 C8 N2 C9 -4.5(3) . . . . ?
