#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/82/1508253.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_1508253
loop_
_publ_author_name
'Yu, Wenquan'
'Gill, Tina'
'Wang, Lijuan'
'Du, Yanming'
'Ye, Hong'
'Qu, Xiaowang'
'Guo, Ju-Tao'
'Cuconati, Andrea'
'Zhao, Kang'
'Block, Timothy M.'
'Xu, Xiaodong'
'Chang, Jinhong'
_publ_section_title
;
 Design, Synthesis, and Biological Evaluation of N-Alkylated
 Deoxynojirimycin (DNJ) Derivatives for the Treatment of Dengue Virus
 Infection.
;
_journal_issue                   13
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              6061
_journal_page_last               6075
_journal_paper_doi               10.1021/jm300171v
_journal_volume                  55
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_sum            'C18 H27 F2 N O5'
_chemical_formula_weight         375.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.0480(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6384(5)
_cell_length_b                   7.1514(3)
_cell_length_c                   19.5985(8)
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.68
_cell_measurement_theta_min      3.02
_cell_volume                     1876.09(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17793
_diffrn_reflns_theta_full        28.74
_diffrn_reflns_theta_max         28.74
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_correction_T_min  0.9417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2611
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0263
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0463P)²+0.5239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0729
_reflns_number_gt                2521
_reflns_number_total             2611
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jm300171v_si_002.cif
_cod_data_source_block           11mxu1h
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'C2   '
_cod_database_code               1508253
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.40989(8) 1.66926(14) 0.56464(5) 0.0286(2) Uani 1 1 d .
F2 F 0.39614(9) 1.03178(16) 0.71190(5) 0.0347(3) Uani 1 1 d .
O1 O 0.55240(6) 0.41684(14) 0.10284(5) 0.01349(19) Uani 1 1 d D
H1O H 0.5672(14) 0.351(2) 0.0713(8) 0.020 Uiso 1 1 d D
O2 O 0.39294(7) 0.21676(13) 0.01908(5) 0.01205(18) Uani 1 1 d D
H2O H 0.4272(12) 0.128(2) 0.0384(9) 0.018 Uiso 1 1 d D
O3 O 0.19270(6) 0.30801(14) 0.04042(5) 0.01152(18) Uani 1 1 d D
H3O H 0.1794(13) 0.284(3) -0.0019(5) 0.017 Uiso 1 1 d D
O4 O 0.51264(7) 0.90634(14) 0.07588(5) 0.01367(19) Uani 1 1 d D
H4O H 0.5649(10) 0.886(3) 0.0600(9) 0.021 Uiso 1 1 d D
O5 O 0.36606(8) 1.35242(16) 0.49503(5) 0.0219(2) Uani 1 1 d .
N1 N 0.33831(7) 0.72540(15) 0.10830(5) 0.0095(2) Uani 1 1 d .
C1 C 0.43998(9) 0.64836(18) 0.13187(6) 0.0095(2) Uani 1 1 d .
H1 H 0.4431 0.5913 0.1760 0.011 Uiso 1 1 calc R
C2 C 0.45617(9) 0.49806(18) 0.07978(6) 0.0096(2) Uani 1 1 d .
H2 H 0.4550 0.5558 0.0360 0.011 Uiso 1 1 calc R
C3 C 0.37571(9) 0.34648(17) 0.07098(6) 0.0097(2) Uani 1 1 d .
H3 H 0.3787 0.2827 0.1138 0.012 Uiso 1 1 calc R
C4 C 0.27401(9) 0.43827(17) 0.04968(6) 0.0094(2) Uani 1 1 d .
H4 H 0.2723 0.5042 0.0074 0.011 Uiso 1 1 calc R
C5 C 0.26253(9) 0.57782(17) 0.10650(6) 0.0101(2) Uani 1 1 d .
H5A H 0.1948 0.6333 0.0966 0.012 Uiso 1 1 calc R
H5B H 0.2718 0.5137 0.1521 0.012 Uiso 1 1 calc R
C6 C 0.52038(9) 0.79989(19) 0.13860(6) 0.0121(2) Uani 1 1 d .
H6A H 0.5137 0.8847 0.1774 0.015 Uiso 1 1 calc R
H6B H 0.5872 0.7407 0.1498 0.015 Uiso 1 1 calc R
C7 C 0.31649(9) 0.89067(17) 0.14823(6) 0.0113(2) Uani 1 1 d .
H7A H 0.2477 0.9328 0.1288 0.014 Uiso 1 1 calc R
H7B H 0.3624 0.9926 0.1407 0.014 Uiso 1 1 calc R
C8 C 0.32548(10) 0.86357(19) 0.22682(7) 0.0145(2) Uani 1 1 d .
H8A H 0.2713 0.7802 0.2356 0.017 Uiso 1 1 calc R
H8B H 0.3901 0.8028 0.2460 0.017 Uiso 1 1 calc R
C9 C 0.31901(10) 1.0502(2) 0.26364(7) 0.0158(3) Uani 1 1 d .
H9A H 0.3686 1.1381 0.2508 0.019 Uiso 1 1 calc R
H9B H 0.2517 1.1047 0.2478 0.019 Uiso 1 1 calc R
C10 C 0.33858(10) 1.0277(2) 0.34257(7) 0.0174(3) Uani 1 1 d .
H10A H 0.4047 0.9683 0.3579 0.021 Uiso 1 1 calc R
H10B H 0.2875 0.9430 0.3553 0.021 Uiso 1 1 calc R
C11 C 0.33645(11) 1.2134(2) 0.38132(7) 0.0191(3) Uani 1 1 d .
H11A H 0.3899 1.2967 0.3713 0.023 Uiso 1 1 calc R
H11B H 0.2715 1.2763 0.3654 0.023 Uiso 1 1 calc R
C12 C 0.35171(11) 1.1764(2) 0.45883(7) 0.0197(3) Uani 1 1 d .
H12A H 0.2926 1.1114 0.4700 0.024 Uiso 1 1 calc R
H12B H 0.4109 1.0955 0.4735 0.024 Uiso 1 1 calc R
C13 C 0.38462(10) 1.3427(2) 0.56555(7) 0.0189(3) Uani 1 1 d .
C14 C 0.40752(11) 1.5107(2) 0.60168(8) 0.0203(3) Uani 1 1 d .
C15 C 0.42614(11) 1.5191(2) 0.67340(8) 0.0224(3) Uani 1 1 d .
H15 H 0.4413 1.6356 0.6963 0.027 Uiso 1 1 calc R
C16 C 0.42275(11) 1.3573(2) 0.71203(8) 0.0237(3) Uani 1 1 d .
H16 H 0.4354 1.3602 0.7614 0.028 Uiso 1 1 calc R
C17 C 0.40043(11) 1.1928(2) 0.67604(8) 0.0229(3) Uani 1 1 d .
C18 C 0.38130(11) 1.1802(2) 0.60383(8) 0.0214(3) Uani 1 1 d .
H18 H 0.3663 1.0632 0.5813 0.026 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 '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'
F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C2 O1 H1O 109.5(13)
C3 O2 H2O 108.9(13)
C4 O3 H3O 106.1(13)
C6 O4 H4O 107.2(14)
C13 O5 C12 115.98(12)
C5 N1 C7 111.96(9)
C5 N1 C1 110.59(10)
C7 N1 C1 113.80(9)
N1 C1 C2 107.45(9)
N1 C1 C6 112.10(10)
C2 C1 C6 111.30(10)
N1 C1 H1 108.6
C2 C1 H1 108.6
C6 C1 H1 108.6
O1 C2 C1 108.47(9)
O1 C2 C3 110.11(10)
C1 C2 C3 112.45(10)
O1 C2 H2 108.6
C1 C2 H2 108.6
C3 C2 H2 108.6
O2 C3 C4 110.55(10)
O2 C3 C2 109.16(9)
C4 C3 C2 108.82(10)
O2 C3 H3 109.4
C4 C3 H3 109.4
C2 C3 H3 109.4
O3 C4 C3 113.43(10)
O3 C4 C5 109.43(9)
C3 C4 C5 107.34(9)
O3 C4 H4 108.8
C3 C4 H4 108.8
C5 C4 H4 108.8
N1 C5 C4 108.46(9)
N1 C5 H5A 110.0
C4 C5 H5A 110.0
N1 C5 H5B 110.0
C4 C5 H5B 110.0
H5A C5 H5B 108.4
O4 C6 C1 111.64(10)
O4 C6 H6A 109.3
C1 C6 H6A 109.3
O4 C6 H6B 109.3
C1 C6 H6B 109.3
H6A C6 H6B 108.0
N1 C7 C8 116.42(10)
N1 C7 H7A 108.2
C8 C7 H7A 108.2
N1 C7 H7B 108.2
C8 C7 H7B 108.2
H7A C7 H7B 107.3
C9 C8 C7 111.29(11)
C9 C8 H8A 109.4
C7 C8 H8A 109.4
C9 C8 H8B 109.4
C7 C8 H8B 109.4
H8A C8 H8B 108.0
C10 C9 C8 111.81(12)
C10 C9 H9A 109.3
C8 C9 H9A 109.3
C10 C9 H9B 109.3
C8 C9 H9B 109.3
H9A C9 H9B 107.9
C9 C10 C11 113.22(12)
C9 C10 H10A 108.9
C11 C10 H10A 108.9
C9 C10 H10B 108.9
C11 C10 H10B 108.9
H10A C10 H10B 107.7
C12 C11 C10 109.46(12)
C12 C11 H11A 109.8
C10 C11 H11A 109.8
C12 C11 H11B 109.8
C10 C11 H11B 109.8
H11A C11 H11B 108.2
O5 C12 C11 108.69(12)
O5 C12 H12A 110.0
C11 C12 H12A 110.0
O5 C12 H12B 110.0
C11 C12 H12B 110.0
H12A C12 H12B 108.3
O5 C13 C18 124.98(13)
O5 C13 C14 116.83(14)
C18 C13 C14 118.18(13)
F1 C14 C15 119.47(14)
F1 C14 C13 118.36(12)
C15 C14 C13 122.16(15)
C14 C15 C16 120.00(15)
C14 C15 H15 120.0
C16 C15 H15 120.0
C17 C16 C15 117.42(13)
C17 C16 H16 121.3
C15 C16 H16 121.3
F2 C17 C16 119.20(13)
F2 C17 C18 117.01(14)
C16 C17 C18 123.79(15)
C13 C18 C17 118.44(14)
C13 C18 H18 120.8
C17 C18 H18 120.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C14 1.3500(19)
F2 C17 1.3558(19)
O1 C2 1.4270(14)
O1 H1O 0.832(9)
O2 C3 1.4291(14)
O2 H2O 0.833(9)
O3 C4 1.4329(14)
O3 H3O 0.833(9)
O4 C6 1.4325(15)
O4 H4O 0.843(9)
O5 C13 1.3583(17)
O5 C12 1.4400(17)
N1 C5 1.4728(15)
N1 C7 1.4789(15)
N1 C1 1.4813(15)
C1 C2 1.5273(16)
C1 C6 1.5293(17)
C1 H1 0.9500
C2 C3 1.5286(17)
C2 H2 0.9500
C3 C4 1.5189(16)
C3 H3 0.9500
C4 C5 1.5255(16)
C4 H4 0.9500
C5 H5A 0.9900
C5 H5B 0.9900
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.5337(17)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.5280(18)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.5271(18)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.533(2)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.5166(19)
C11 H11A 0.9900
C11 H11B 0.9900
C12 H12A 0.9900
C12 H12B 0.9900
C13 C18 1.389(2)
C13 C14 1.399(2)
C14 C15 1.381(2)
C15 C16 1.388(2)
C15 H15 0.9500
C16 C17 1.376(2)
C16 H16 0.9500
C17 C18 1.392(2)
C18 H18 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 28643221 ChemSpider
