#------------------------------------------------------------------------------
#$Date: 2020-02-27 02:20:36 +0200 (Thu, 27 Feb 2020) $
#$Revision: 248467 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/79/4037963.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_4037963
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            'C15 H20 N2 O6'
_chemical_formula_weight         324.33
_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
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.91240(8)
_cell_length_b                   6.26542(6)
_cell_length_c                   40.7670(4)
_cell_measurement_reflns_used    39035
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.2210
_cell_measurement_theta_min      4.3350
_cell_volume                     1510.16(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-2017
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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  0.0425
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            59504
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.476
_diffrn_reflns_theta_min         2.167
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.935
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       lath
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1240 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0248
_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)+(0.0335P)²+0.3659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0630
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                3126
_reflns_number_total             3181
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03425_si_005.cif
_cod_data_source_block           kolbenz
_cod_database_code               4037963
_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   0.872
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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 0.7222(2) 0.3361(2) 0.40207(3) 0.0130(3) Uani 1 1 d . . . . .
H1 H 0.879984 0.308889 0.394278 0.016 Uiso 1 1 calc R U . . .
C2 C 0.5552(2) 0.2899(2) 0.37391(3) 0.0130(3) Uani 1 1 d . . . . .
H2 H 0.403623 0.244263 0.382248 0.016 Uiso 1 1 calc R U . . .
C3 C 0.5446(2) 0.5033(2) 0.35653(3) 0.0151(3) Uani 1 1 d . . . . .
H3 H 0.397736 0.526496 0.344900 0.018 Uiso 1 1 calc R U . . .
C4 C 0.5873(3) 0.6678(2) 0.38331(3) 0.0151(3) Uani 1 1 d . . . . .
H4 H 0.689243 0.782456 0.374789 0.018 Uiso 1 1 calc R U . . .
C5 C 0.3713(3) 0.7655(2) 0.39588(4) 0.0180(3) Uani 1 1 d . . . . .
H5A H 0.401925 0.848480 0.416065 0.022 Uiso 1 1 calc R U . . .
H5B H 0.307484 0.863352 0.379217 0.022 Uiso 1 1 calc R U . . .
C6 C 0.7603(3) 0.2681(2) 0.32571(3) 0.0157(3) Uani 1 1 d . . . . .
C7 C 1.0111(3) 0.2156(2) 0.32605(4) 0.0201(3) Uani 1 1 d . . . . .
H7A H 1.073152 0.243341 0.348203 0.024 Uiso 1 1 calc R U . . .
H7B H 1.091156 0.309432 0.310335 0.024 Uiso 1 1 calc R U . . .
C8 C 1.0528(3) -0.0175(3) 0.31686(4) 0.0248(3) Uani 1 1 d . . . . .
H8A H 1.217671 -0.044629 0.315981 0.030 Uiso 1 1 calc R U . . .
H8B H 0.987195 -0.111298 0.333924 0.030 Uiso 1 1 calc R U . . .
C9 C 0.9475(3) -0.0708(3) 0.28371(4) 0.0309(4) Uani 1 1 d . . . . .
H9A H 1.026157 0.010308 0.266275 0.037 Uiso 1 1 calc R U . . .
H9B H 0.967602 -0.224859 0.279135 0.037 Uiso 1 1 calc R U . . .
C10 C 0.6963(3) -0.0166(3) 0.28309(4) 0.0277(4) Uani 1 1 d . . . . .
H10A H 0.614640 -0.111083 0.298536 0.033 Uiso 1 1 calc R U . . .
H10B H 0.635675 -0.042626 0.260807 0.033 Uiso 1 1 calc R U . . .
C11 C 0.6546(3) 0.2168(3) 0.29260(4) 0.0210(3) Uani 1 1 d . . . . .
H11A H 0.719971 0.311549 0.275638 0.025 Uiso 1 1 calc R U . . .
H11B H 0.489762 0.243964 0.293579 0.025 Uiso 1 1 calc R U . . .
C12 C 0.4910(3) 0.2467(2) 0.45066(3) 0.0159(3) Uani 1 1 d . . . . .
H12 H 0.388087 0.355534 0.444293 0.019 Uiso 1 1 calc R U . . .
C13 C 0.4480(3) 0.1325(2) 0.47795(4) 0.0179(3) Uani 1 1 d . . . . .
H13 H 0.313614 0.157452 0.490126 0.021 Uiso 1 1 calc R U . . .
C14 C 0.6068(3) -0.0276(2) 0.48860(3) 0.0171(3) Uani 1 1 d . . . . .
C15 C 0.8298(2) 0.0460(2) 0.43879(3) 0.0144(3) Uani 1 1 d . . . . .
O1 O 0.69871(18) 0.55440(15) 0.40998(2) 0.0155(2) Uani 1 1 d . . . . .
O2 O 0.64287(18) 0.14497(16) 0.35041(2) 0.0151(2) Uani 1 1 d . . . . .
O3 O 0.73239(19) 0.48725(16) 0.33446(3) 0.0192(2) Uani 1 1 d . . . . .
O4 O 0.21408(19) 0.59818(17) 0.40276(3) 0.0200(2) Uani 1 1 d . . . . .
H04 H 0.094(4) 0.653(4) 0.4106(6) 0.042(7) Uiso 1 1 d . . . . .
O5 O 0.5966(2) -0.12949(18) 0.51440(3) 0.0238(3) Uani 1 1 d . . . . .
O6 O 0.98823(19) -0.00046(17) 0.42108(3) 0.0199(2) Uani 1 1 d . . . . .
N1 N 0.6799(2) 0.20994(19) 0.43173(3) 0.0137(2) Uani 1 1 d . . . . .
N2 N 0.7851(2) -0.0615(2) 0.46743(3) 0.0167(3) Uani 1 1 d . . . . .
H02 H 0.887(4) -0.162(4) 0.4723(5) 0.032(6) 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 108.48(10) . . ?
O1 C1 C2 106.79(11) . . ?
N1 C1 C2 113.81(11) . . ?
O2 C2 C3 105.33(11) . . ?
O2 C2 C1 112.89(12) . . ?
C3 C2 C1 102.05(11) . . ?
O3 C3 C2 101.53(11) . . ?
O3 C3 C4 111.68(12) . . ?
C2 C3 C4 104.79(11) . . ?
O1 C4 C5 109.12(11) . . ?
O1 C4 C3 106.27(11) . . ?
C5 C4 C3 112.25(12) . . ?
O4 C5 C4 108.69(11) . . ?
O3 C6 O2 106.44(11) . . ?
O3 C6 C7 108.58(12) . . ?
O2 C6 C7 110.30(12) . . ?
O3 C6 C11 112.15(12) . . ?
O2 C6 C11 107.93(12) . . ?
C7 C6 C11 111.33(13) . . ?
C6 C7 C8 111.23(13) . . ?
C9 C8 C7 111.17(14) . . ?
C10 C9 C8 111.34(13) . . ?
C9 C10 C11 111.43(15) . . ?
C6 C11 C10 111.08(13) . . ?
C13 C12 N1 121.80(14) . . ?
C12 C13 C14 119.73(14) . . ?
O5 C14 N2 119.50(14) . . ?
O5 C14 C13 125.87(14) . . ?
N2 C14 C13 114.62(12) . . ?
O6 C15 N2 122.32(13) . . ?
O6 C15 N1 123.05(13) . . ?
N2 C15 N1 114.63(12) . . ?
C1 O1 C4 110.27(10) . . ?
C2 O2 C6 107.74(10) . . ?
C6 O3 C3 108.31(11) . . ?
C12 N1 C15 121.73(12) . . ?
C12 N1 C1 120.70(12) . . ?
C15 N1 C1 117.48(12) . . ?
C15 N2 C14 127.13(13) . . ?
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 1.4123(16) . ?
C1 N1 1.4661(17) . ?
C1 C2 1.5417(19) . ?
C2 O2 1.4179(16) . ?
C2 C3 1.5148(19) . ?
C3 O3 1.4324(17) . ?
C3 C4 1.522(2) . ?
C4 O1 1.4562(16) . ?
C4 C5 1.506(2) . ?
C5 O4 1.4287(18) . ?
C6 O3 1.4286(17) . ?
C6 O2 1.4462(17) . ?
C6 C7 1.519(2) . ?
C6 C11 1.522(2) . ?
C7 C8 1.527(2) . ?
C8 C9 1.525(2) . ?
C9 C10 1.524(3) . ?
C10 C11 1.533(2) . ?
C12 C13 1.347(2) . ?
C12 N1 1.3771(19) . ?
C13 C14 1.441(2) . ?
C14 O5 1.2318(18) . ?
C14 N2 1.379(2) . ?
C15 O6 1.2180(18) . ?
C15 N2 1.3737(18) . ?
C15 N1 1.3868(18) . ?
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 O1 0.85(3) 2.42(2) 3.0735(16) 134(2) 1_455 yes
O4 H04 O6 0.85(3) 2.30(3) 2.9434(15) 133(2) 1_465 yes
N2 H02 O5 0.89(2) 1.88(2) 2.7727(17) 176(2) 4_546 yes
C4 H4 O2 1.00 2.49 3.2932(17) 136.6 1_565 yes
C12 H12 O4 0.95 2.50 3.3679(18) 152.4 . 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 142.32(11) . . . . ?
N1 C1 C2 O2 -98.01(13) . . . . ?
O1 C1 C2 C3 29.76(14) . . . . ?
N1 C1 C2 C3 149.43(11) . . . . ?
O2 C2 C3 O3 -31.53(14) . . . . ?
C1 C2 C3 O3 86.56(12) . . . . ?
O2 C2 C3 C4 -147.88(12) . . . . ?
C1 C2 C3 C4 -29.78(14) . . . . ?
O3 C3 C4 O1 -88.75(13) . . . . ?
C2 C3 C4 O1 20.36(14) . . . . ?
O3 C3 C4 C5 152.03(12) . . . . ?
C2 C3 C4 C5 -98.86(13) . . . . ?
O1 C4 C5 O4 -69.38(14) . . . . ?
C3 C4 C5 O4 48.15(16) . . . . ?
O3 C6 C7 C8 180.00(11) . . . . ?
O2 C6 C7 C8 63.72(16) . . . . ?
C11 C6 C7 C8 -56.07(17) . . . . ?
C6 C7 C8 C9 55.67(17) . . . . ?
C7 C8 C9 C10 -55.03(19) . . . . ?
C8 C9 C10 C11 54.73(19) . . . . ?
O3 C6 C11 C10 177.42(13) . . . . ?
O2 C6 C11 C10 -65.66(16) . . . . ?
C7 C6 C11 C10 55.53(17) . . . . ?
C9 C10 C11 C6 -54.89(17) . . . . ?
N1 C12 C13 C14 2.3(2) . . . . ?
C12 C13 C14 O5 173.57(15) . . . . ?
C12 C13 C14 N2 -5.3(2) . . . . ?
N1 C1 O1 C4 -141.04(11) . . . . ?
C2 C1 O1 C4 -17.99(15) . . . . ?
C5 C4 O1 C1 119.86(12) . . . . ?
C3 C4 O1 C1 -1.39(15) . . . . ?
C3 C2 O2 C6 21.04(15) . . . . ?
C1 C2 O2 C6 -89.50(13) . . . . ?
O3 C6 O2 C2 -2.18(15) . . . . ?
C7 C6 O2 C2 115.44(13) . . . . ?
C11 C6 O2 C2 -122.74(13) . . . . ?
O2 C6 O3 C3 -18.99(15) . . . . ?
C7 C6 O3 C3 -137.73(12) . . . . ?
C11 C6 O3 C3 98.82(13) . . . . ?
C2 C3 O3 C6 30.75(14) . . . . ?
C4 C3 O3 C6 141.95(12) . . . . ?
C13 C12 N1 C15 3.5(2) . . . . ?
C13 C12 N1 C1 179.78(13) . . . . ?
O6 C15 N1 C12 174.14(14) . . . . ?
N2 C15 N1 C12 -5.59(19) . . . . ?
O6 C15 N1 C1 -2.3(2) . . . . ?
N2 C15 N1 C1 177.99(12) . . . . ?
O1 C1 N1 C12 49.33(17) . . . . ?
C2 C1 N1 C12 -69.38(16) . . . . ?
O1 C1 N1 C15 -134.21(12) . . . . ?
C2 C1 N1 C15 107.08(14) . . . . ?
O6 C15 N2 C14 -177.50(14) . . . . ?
N1 C15 N2 C14 2.2(2) . . . . ?
O5 C14 N2 C15 -175.89(14) . . . . ?
C13 C14 N2 C15 3.1(2) . . . . ?
