#------------------------------------------------------------------------------
#$Date: 2017-12-19 12:08:12 +0200 (Tue, 19 Dec 2017) $
#$Revision: 204345 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/84/1548477.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_1548477
loop_
_publ_author_name
'Milan Bergeron-Brlek'
'Michael Meanwell'
'Robert Britton'
_publ_section_title
;
 Direct synthesis of imino-C-nucleoside analogues and other biologically
 active iminosugars
;
_journal_name_full               'Nature Communications'
_journal_page_first              6903
_journal_paper_doi               10.1038/ncomms7903
_journal_volume                  6
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_sum            'C18 H23 N O3'
_chemical_formula_weight         301.37
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3102(3)
_cell_length_b                   9.6848(3)
_cell_length_c                   18.5136(6)
_cell_measurement_reflns_used    7941
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      2.37
_cell_volume                     1669.32(9)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11009
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.411
_diffrn_reflns_theta_min         2.200
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrich , 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       Block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.568
_exptl_crystal_size_mid          0.394
_exptl_crystal_size_min          0.208
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 1166 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.6(4)
_refine_ls_extinction_coef       0.0081(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3081
_refine_ls_number_restraints     177
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0320
_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)+(0.0317P)²+0.2569P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0798
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2886
_reflns_number_total             3081
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ncomms7903-s5.cif
_cod_data_source_block           mo_1MM033_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_database_code               1548477
_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   0.955
_shelx_estimated_absorpt_t_max   0.983
_shelxl_version_number           2013-2
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
O1 O 1.00723(17) 0.00370(16) 1.02069(8) 0.0472(4) Uani 1 1 d . U . . .
N1 N 0.81139(17) -0.02339(16) 0.87460(9) 0.0380(4) Uani 1 1 d . U . . .
C1 C 1.2528(3) -0.2982(3) 0.89622(17) 0.0699(8) Uani 1 1 d . U . . .
H1 H 1.3313 -0.3464 0.9145 0.084 Uiso 1 1 calc R U . . .
O2 O 0.97682(15) 0.27126(13) 0.95577(7) 0.0372(3) Uani 1 1 d . U . . .
C2 C 1.1537(2) -0.2374(2) 0.87313(14) 0.0521(6) Uani 1 1 d . U . . .
C3 C 1.0285(2) -0.1623(2) 0.84539(12) 0.0474(5) Uani 1 1 d . U . . .
H3A H 0.9675 -0.2261 0.8191 0.057 Uiso 1 1 calc R U . . .
H3B H 1.0608 -0.0922 0.8117 0.057 Uiso 1 1 calc R U . . .
O3 O 0.74602(15) 0.34526(14) 0.91964(9) 0.0443(4) Uani 1 1 d . U . . .
C4 C 0.9402(2) -0.0934(2) 0.90533(11) 0.0368(4) Uani 1 1 d . U . . .
H4 H 0.9092 -0.1637 0.9401 0.044 Uiso 1 1 calc R U . . .
C5 C 1.0262(2) 0.01908(19) 0.94522(10) 0.0354(4) Uani 1 1 d . U . . .
H5 H 1.1281 0.0159 0.9321 0.042 Uiso 1 1 calc R U . . .
C6 C 0.9547(2) 0.14815(19) 0.91593(10) 0.0335(4) Uani 1 1 d . U . . .
H6 H 0.9880 0.1631 0.8663 0.040 Uiso 1 1 calc R U . . .
C7 C 0.7988(2) 0.1071(2) 0.91374(11) 0.0372(4) Uani 1 1 d . U . . .
H7 H 0.7631 0.0905 0.9628 0.045 Uiso 1 1 calc R U . . .
C9 C 0.9553(3) 0.4287(2) 0.85371(12) 0.0506(6) Uani 1 1 d . U . . .
H9A H 0.9004 0.5052 0.8356 0.076 Uiso 1 1 calc R U . . .
H9B H 0.9505 0.3535 0.8200 0.076 Uiso 1 1 calc R U . . .
H9C H 1.0536 0.4564 0.8598 0.076 Uiso 1 1 calc R U . . .
C8 C 0.7154(2) 0.2221(2) 0.87861(14) 0.0480(5) Uani 1 1 d . U . . .
H8A H 0.7450 0.2336 0.8287 0.058 Uiso 1 1 calc R U . . .
H8B H 0.6133 0.2020 0.8796 0.058 Uiso 1 1 calc R U . . .
C10 C 0.8946(2) 0.3830(2) 0.92577(11) 0.0378(5) Uani 1 1 d . U . . .
C11 C 0.9005(2) 0.4969(2) 0.98090(13) 0.0508(6) Uani 1 1 d . U . . .
H11A H 0.8372 0.5702 0.9666 0.076 Uiso 1 1 calc R U . . .
H11B H 0.9969 0.5316 0.9842 0.076 Uiso 1 1 calc R U . . .
H11C H 0.8713 0.4617 1.0271 0.076 Uiso 1 1 calc R U . . .
C12 C 0.6802(2) -0.1064(2) 0.87359(12) 0.0443(5) Uani 1 1 d . U . . .
H12A H 0.5979 -0.0452 0.8714 0.053 Uiso 1 1 calc R U . . .
H12B H 0.6740 -0.1582 0.9183 0.053 Uiso 1 1 calc R U . . .
H12 H 1.070(3) 0.061(3) 1.0431(15) 0.076(9) Uiso 1 1 d . . . . .
C13 C 0.6731(2) -0.2060(2) 0.81088(11) 0.0372(5) Uani 1 1 d . U . . .
C14 C 0.6338(3) -0.3416(2) 0.82178(13) 0.0494(6) Uani 1 1 d . U . . .
H14 H 0.6124 -0.3715 0.8683 0.059 Uiso 1 1 calc R U . . .
C15 C 0.6255(3) -0.4339(3) 0.76514(16) 0.0628(7) Uani 1 1 d . U . . .
H15 H 0.5990 -0.5250 0.7737 0.075 Uiso 1 1 calc R U . . .
C16 C 0.6561(3) -0.3917(3) 0.69694(16) 0.0642(7) Uani 1 1 d . U . . .
H16 H 0.6516 -0.4543 0.6589 0.077 Uiso 1 1 calc R U . . .
C17 C 0.6937(3) -0.2567(3) 0.68393(14) 0.0657(7) Uani 1 1 d . U . . .
H17 H 0.7137 -0.2276 0.6371 0.079 Uiso 1 1 calc R U . . .
C18 C 0.7016(3) -0.1639(3) 0.74090(13) 0.0528(6) Uani 1 1 d . U . . .
H18 H 0.7263 -0.0724 0.7320 0.063 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C7 N1 C12 114.52(16) . .
C7 N1 C4 105.56(15) . .
C12 N1 C4 115.25(15) . .
C6 O2 C10 110.80(14) . .
C1 C2 C3 179.0(3) . .
C2 C3 C4 112.85(19) . .
C10 O3 C8 116.29(15) . .
N1 C4 C3 110.68(16) . .
N1 C4 C5 106.24(15) . .
C3 C4 C5 112.08(17) . .
O1 C5 C6 112.64(17) . .
O1 C5 C4 109.51(16) . .
C6 C5 C4 100.57(15) . .
O2 C6 C7 112.12(16) . .
O2 C6 C5 116.35(15) . .
C7 C6 C5 102.40(16) . .
N1 C7 C6 99.48(15) . .
N1 C7 C8 117.82(16) . .
C6 C7 C8 108.27(17) . .
O3 C8 C7 106.39(16) . .
O3 C10 O2 110.60(16) . .
O3 C10 C11 106.02(16) . .
O2 C10 C11 105.70(16) . .
O3 C10 C9 111.38(18) . .
O2 C10 C9 111.18(17) . .
C11 C10 C9 111.69(18) . .
N1 C12 C13 113.43(17) . .
C14 C13 C18 117.9(2) . .
C14 C13 C12 120.5(2) . .
C18 C13 C12 121.55(19) . .
C13 C14 C15 121.4(2) . .
C16 C15 C14 120.0(3) . .
C15 C16 C17 120.2(2) . .
C16 C17 C18 119.8(3) . .
C13 C18 C17 120.7(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C5 1.416(2) .
N1 C7 1.461(2) .
N1 C12 1.462(3) .
N1 C4 1.490(2) .
C1 C2 1.176(3) .
O2 C6 1.417(2) .
O2 C10 1.437(2) .
C2 C3 1.466(3) .
C3 C4 1.534(3) .
O3 C10 1.435(2) .
O3 C8 1.443(2) .
C4 C5 1.540(3) .
C5 C6 1.516(3) .
C6 C7 1.505(3) .
C7 C8 1.506(3) .
C9 C10 1.515(3) .
C10 C11 1.504(3) .
C12 C13 1.510(3) .
C13 C14 1.378(3) .
C13 C18 1.384(3) .
C14 C15 1.381(3) .
C15 C16 1.357(4) .
C16 C17 1.375(4) .
C17 C18 1.388(3) .
