#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/97/2009743.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2009743
loop_
_publ_author_name
'Linden, Anthony'
'Hoos, Roland'
'Vasella, Andrea'
_publ_section_title
;
 1-Deoxynojirimycin hydrochloride
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              746
_journal_page_last               749
_journal_paper_doi               10.1107/S0108270193012417
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C6 H14 N O4 1+, Cl 1-'
_chemical_formula_sum            'C6 H14 Cl N O4'
_chemical_formula_weight         199.63
_chemical_name_common            ' 1-deoxynojirimycin hydrochloride'
_chemical_name_systematic        ' 1,5-Dideoxy-1,5-iminium-glucitol chloride'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.648(3)
_cell_length_b                   20.473(5)
_cell_length_c                   6.400(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    173.0(10)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      19.5
_cell_volume                     871.1(6)
_computing_cell_refinement
;
MSC/AFC Diffractometer Control (Molecular Structure Corporation, 1991)
;
_computing_data_collection
;
MSC/AFC Diffractometer Control (Molecular Structure Corporation, 1991)
;
_computing_data_reduction
;
TEXSAN: PROCESS (Molecular Structure Corporation, 1989)
;
_computing_molecular_graphics    'ORTEPII, (Johnson, 1976)'
_computing_publication_material
;
TEXSAN: FINISH (Molecular Structure Corporation, 1989)
;
_computing_structure_refinement
;
TEXSAN: LS (Molecular Structure Corporation, 1989)
;
_computing_structure_solution    'SHELXS86 Patterson (Sheldrick, 1990)'
_diffrn_ambient_temperature      173.0(10)
_diffrn_measurement_device       'Rigaku AFC-5R diffractometer'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_number            3650
_diffrn_reflns_theta_max         30
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        insignificant
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.412
_exptl_absorpt_correction_T_max  1.176
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   'empirical (DIFABS: Walker & Stuart, 1983)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.15
_refine_ls_abs_structure_details
;
The absolute configuration was determined by using the CRYSTALS program
system (Carruthers & Watkin, 1986) to refine the final atomic coordinates
together with the enantiopole parameter (Flack, 1983).  The refined value of
the enantiopole parameter was 0.00(5), thus confirming that the atomic
coordinates represented the correct enantiomorph.
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     'not applied'
_refine_ls_goodness_of_fit_obs   1.583
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_obs          0.0233
_refine_ls_shift/esd_max         0.0003
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/(σ²(Fₒ)+(0.005Fₒ)²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0256
_refine_ls_wR_factor_obs         0.0250
_reflns_number_observed          2340
_reflns_number_total             2526
_reflns_observed_criterion       'I > 3\s(I)'
_cod_data_source_file            sh1087.cif
_cod_data_source_block           VS9305
_cod_depositor_comments
;
 Changing the _atom_site_occupancy data item value from '?' to '1'
 for all fully occupied atom sites.

 Antanas Vaitkus,
 2017-02-13

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/(\s^2^(F~o~)+(0.005F~o~)^2^)'
was changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/(\s^2^(F~o~)+(0.005F~o~)^2^)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        871.1(5)
_cod_database_code               2009743
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
-x,1/2+y,1/2-z
1/2+x,1/2-y,-z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
_atom_site_aniso_type_symbol
Cl(1) 0.02100(10) 0.02270(10) 0.02320(10) 0.00180(10) -0.0004(2) -0.00480(10)
Cl
O(2) 0.0239(5) 0.0189(4) 0.0304(5) -0.0009(4) -0.0110(5) -0.0006(4) O
O(3) 0.0272(5) 0.0215(4) 0.0191(5) 0.0054(4) -0.0006(4) -0.0047(4) O
O(4) 0.0316(5) 0.0248(5) 0.0207(5) 0.0122(4) -0.0016(5) 0.0011(4) O
O(6) 0.0278(5) 0.0354(5) 0.0232(5) -0.0075(4) 0.0003(4) -0.0093(4) O
N(5) 0.0171(5) 0.0169(5) 0.0194(5) -0.0009(4) 0.0000(5) -0.0021(4) N
C(1) 0.0158(5) 0.0226(6) 0.0226(6) 0.0012(5) -0.0013(5) -0.0049(5) C
C(2) 0.0173(5) 0.0178(6) 0.0182(6) -0.0006(5) -0.0037(5) -0.0011(5) C
C(3) 0.0197(5) 0.0161(6) 0.0171(6) 0.0010(5) -0.0003(5) -0.0017(5) C
C(4) 0.0192(5) 0.0180(5) 0.0169(6) 0.0039(4) -0.0004(5) 0.0011(4) C
C(5) 0.0189(5) 0.0176(5) 0.0170(6) -0.0011(4) -0.0007(5) 0.0021(5) C
C(6) 0.0209(5) 0.0241(6) 0.0201(6) -0.0003(6) -0.0032(6) -0.0013(5) C
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_occupancy
_atom_site_type_symbol
Cl(1) 0.94566(4) 0.017010(10) 0.25789(5) 0.02231(8) Uani ? ? 1 Cl
O(2) 0.4547(2) 0.35143(4) -0.0119(2) 0.0244(3) Uani ? ? 1 O
O(3) 0.79590(10) 0.27121(5) -0.0283(2) 0.0226(3) Uani ? ? 1 O
O(4) 1.0311(2) 0.26318(5) 0.3529(2) 0.0257(3) Uani ? ? 1 O
O(6) 0.99290(10) 0.42103(5) 0.7763(2) 0.0288(3) Uani ? ? 1 O
N(5) 0.7508(2) 0.41684(5) 0.4328(2) 0.0178(3) Uani ? ? 1 N
C(1) 0.5710(2) 0.40169(6) 0.3016(2) 0.0203(3) Uani ? ? 1 C
C(2) 0.6326(2) 0.36609(6) 0.1038(2) 0.0178(3) Uani ? ? 1 C
C(3) 0.7414(2) 0.30373(6) 0.1602(2) 0.0176(3) Uani ? ? 1 C
C(4) 0.9280(2) 0.32076(6) 0.2890(2) 0.0180(3) Uani ? ? 1 C
C(5) 0.8728(2) 0.35762(6) 0.4889(2) 0.0178(3) Uani ? ? 1 C
C(6) 1.0573(2) 0.38011(6) 0.6084(2) 0.0217(3) Uani ? ? 1 C
H(2) 0.720(2) 0.3927(7) 0.020(2) 0.019(4) Uiso ? ? 1 H
H(3) 0.653(2) 0.2763(6) 0.250(2) 0.015(3) Uiso ? ? 1 H
H(4) 1.011(2) 0.3483(6) 0.201(2) 0.021(4) Uiso ? ? 1 H
H(5) 0.786(2) 0.3300(7) 0.592(3) 0.027(4) Uiso ? ? 1 H
H(11) 0.505(2) 0.4434(6) 0.269(2) 0.021(4) Uiso ? ? 1 H
H(12) 0.479(3) 0.3732(7) 0.392(2) 0.036(5) Uiso ? ? 1 H
H(21) 0.433(3) 0.3831(8) -0.086(3) 0.047(6) Uiso ? ? 1 H
H(31) 0.841(3) 0.2363(9) 0.001(3) 0.035(5) Uiso ? ? 1 H
H(41) 1.098(3) 0.2516(9) 0.245(3) 0.059(6) Uiso ? ? 1 H
H(51) 0.711(2) 0.4388(7) 0.560(3) 0.037(5) Uiso ? ? 1 H
H(52) 0.830(3) 0.4460(8) 0.363(3) 0.041(5) Uiso ? ? 1 H
H(61) 1.087(4) 0.4430(10) 0.808(4) 0.096(9) Uiso ? ? 1 H
H(62) 1.147(2) 0.4035(7) 0.508(2) 0.022(4) Uiso ? ? 1 H
H(63) 1.128(2) 0.3407(8) 0.656(2) 0.034(5) Uiso ? ? 1 H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002 International_Tables_for_X-ray_Crystallography_(1974,_Vol._4)
H 0.000 0.000 International_Tables_for_X-ray_Crystallography_(1974,_Vol._4)
Cl 0.132 0.159 International_Tables_for_X-ray_Crystallography_(1974,_Vol._4)
N 0.004 0.003 International_Tables_for_X-ray_Crystallography_(1974,_Vol._4)
O 0.008 0.006 International_Tables_for_X-ray_Crystallography_(1974,_Vol._4)
loop_
_diffrn_reflns_limit_h_min
_diffrn_reflns_limit_h_max
_diffrn_reflns_limit_k_min
_diffrn_reflns_limit_k_max
_diffrn_reflns_limit_l_min
_diffrn_reflns_limit_l_max
-9 0 -28 0 -9 0
0 9 0 28 0 9
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 3 -1
1 -4 -1
2 -3 -1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C(1) N(5) C(5) . . 113.50(10) yes
N(5) C(1) C(2) . . 110.70(10) yes
O(2) C(2) C(1) . . 108.10(10) yes
O(2) C(2) C(3) . . 110.10(10) yes
C(1) C(2) C(3) . . 109.60(10) yes
O(3) C(3) C(2) . . 108.30(10) yes
O(3) C(3) C(4) . . 110.90(10) yes
C(2) C(3) C(4) . . 108.93(9) yes
O(4) C(4) C(3) . . 110.90(10) yes
O(4) C(4) C(5) . . 106.50(10) yes
C(3) C(4) C(5) . . 111.60(10) yes
N(5) C(5) C(4) . . 109.10(10) yes
N(5) C(5) C(6) . . 108.20(10) yes
C(4) C(5) C(6) . . 112.20(10) yes
O(6) C(6) C(5) . . 108.40(10) yes
C(2) O(2) H(21) . . 106.0(10) ?
C(3) O(3) H(31) . . 108.0(10) ?
C(4) O(4) H(41) . . 104.0(10) ?
C(6) O(6) H(61) . . 107.(2) ?
C(1) N(5) H(51) . . 111.0(10) ?
C(1) N(5) H(52) . . 109.0(10) ?
C(5) N(5) H(51) . . 109.0(10) ?
C(5) N(5) H(52) . . 109.0(10) ?
H(51) N(5) H(52) . . 105.0(10) ?
N(5) C(1) H(11) . . 107.2(8) ?
N(5) C(1) H(12) . . 106.2(9) ?
C(2) C(1) H(11) . . 111.1(8) ?
C(2) C(1) H(12) . . 111.2(9) ?
H(11) C(1) H(12) . . 110.0(10) ?
O(2) C(2) H(2) . . 109.6(8) ?
C(1) C(2) H(2) . . 110.8(8) ?
C(3) C(2) H(2) . . 108.7(8) ?
O(3) C(3) H(3) . . 112.0(8) ?
C(2) C(3) H(3) . . 109.4(7) ?
C(4) C(3) H(3) . . 107.3(8) ?
O(4) C(4) H(4) . . 111.9(8) ?
C(3) C(4) H(4) . . 106.3(8) ?
C(5) C(4) H(4) . . 109.7(7) ?
N(5) C(5) H(5) . . 106.9(8) ?
C(4) C(5) H(5) . . 113.2(8) ?
C(6) C(5) H(5) . . 107.0(9) ?
O(6) C(6) H(62) . . 112.5(9) ?
O(6) C(6) H(63) . . 113.0(9) ?
C(5) C(6) H(62) . . 107.7(8) ?
C(5) C(6) H(63) . . 107.0(9) ?
H(62) C(6) H(63) . . 108.0(10) ?
O(2) H(21) Cl(1) . 4_455 165(2) ?
O(3) H(31) O(2) . 4_555 169(2) ?
O(4) H(41) O(3) . 4_555 169(2) ?
N(5) H(51) Cl(1) . 4_456 145.0(10) ?
N(5) H(52) Cl(1) . 3_755 171(2) ?
O(6) H(61) Cl(1) . 4_556 150(2) ?
H(21) Cl(1) H(51) 4_555 4_556 85.5(6) ?
H(21) Cl(1) H(52) 4_555 3_745 115.7(6) ?
H(21) Cl(1) H(61) 4_555 4_456 67.0(7) ?
H(51) Cl(1) H(52) 4_556 3_745 85.4(6) ?
H(51) Cl(1) H(61) 4_556 4_456 132.5(6) ?
H(52) Cl(1) H(61) 3_745 4_456 140.9(7) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O(2) C(2) . . 1.427(2) yes
O(3) C(3) . . 1.425(2) yes
O(4) C(4) . . 1.4240(10) yes
O(6) C(6) . . 1.428(2) yes
N(5) C(1) . . 1.493(2) yes
N(5) C(5) . . 1.502(2) yes
C(1) C(2) . . 1.517(2) yes
C(2) C(3) . . 1.511(2) yes
C(3) C(4) . . 1.529(2) yes
C(4) C(5) . . 1.530(2) yes
C(5) C(6) . . 1.517(2) yes
O(2) H(21) . . 0.82(2) ?
O(3) H(31) . . 0.80(2) ?
O(4) H(41) . . 0.86(2) ?
N(5) H(51) . . 0.96(2) ?
N(5) H(52) . . 0.91(2) ?
O(6) H(61) . . 0.80(2) ?
C(1) H(11) . . 0.980(10) ?
C(1) H(12) . . 1.03(2) ?
C(2) H(2) . . 0.960(10) ?
C(3) H(3) . . 0.990(10) ?
C(4) H(4) . . 0.970(10) ?
C(5) H(5) . . 1.04(2) ?
C(6) H(62) . . 1.00(2) ?
C(6) H(63) . . 0.98(2) ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
H(21) Cl(1) 2.32(2) 4_455
H(31) O(2) 1.95(2) 4_555
H(41) O(3) 1.97(2) 4_555
H(51) Cl(1) 2.30(2) 4_456
H(52) Cl(1) 2.22(2) 3_755
H(61) Cl(1) 2.55(3) 4_556
O(2) Cl(1) 3.1200(10) 4_455
O(3) O(2) 2.736(2) 4_555
O(4) O(3) 2.813(2) 4_555
N(5) Cl(1) 3.1410(10) 4_456
N(5) Cl(1) 3.1250(10) 3_755
O(6) Cl(1) 3.374(2) 4_556
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_publ_flag
C(1) C(2) C(3) C(4) -59.70(10) yes
C(2) C(3) C(4) C(5) 59.10(10) yes
C(3) C(4) C(5) N(5) -55.00(10) yes
C(4) C(5) N(5) C(1) 53.80(10) yes
C(5) N(5) C(1) C(2) -56.40(10) yes
N(5) C(1) C(2) C(3) 58.50(10) yes
O(6) C(6) C(5) C(4) 172.50(10) yes
O(6) C(6) C(5) N(5) 52.10(10) yes
O(2) C(2) C(1) N(5) 178.50(10) ?
O(2) C(2) C(3) O(3) 60.90(10) ?
O(2) C(2) C(3) C(4) -178.50(10) ?
O(3) C(3) C(2) C(1) 179.60(10) ?
O(3) C(3) C(4) O(4) -63.20(10) ?
O(3) C(3) C(4) C(5) 178.20(10) ?
O(4) C(4) C(3) C(2) 177.70(10) ?
O(4) C(4) C(5) N(5) -176.20(10) ?
O(4) C(4) C(5) C(6) 63.90(10) ?
C(1) N(5) C(5) C(6) 176.10(10) ?
C(3) C(4) C(5) C(6) -174.90(10) ?
O(2) C(2) C(1) H(11) -62.5(8) ?
O(2) C(2) C(1) H(12) 61.0(10) ?
O(2) C(2) C(3) H(3) -61.5(9) ?
O(3) C(3) C(2) H(2) -59.2(9) ?
O(3) C(3) C(4) H(4) 58.6(8) ?
O(4) C(4) C(3) H(3) 59.3(8) ?
O(4) C(4) C(5) H(5) -57.3(9) ?
O(6) C(6) C(5) H(5) -62.7(9) ?
N(5) C(1) C(2) H(2) -61.5(9) ?
N(5) C(5) C(4) H(4) 62.6(9) ?
N(5) C(5) C(6) H(62) -69.8(9) ?
N(5) C(5) C(6) H(63) 174.0(10) ?
C(1) N(5) C(5) H(5) -69.0(9) ?
C(1) C(2) O(2) H(21) 88.0(10) ?
C(1) C(2) C(3) H(3) 57.2(9) ?
C(2) C(1) N(5) H(51) -179.0(10) ?
C(2) C(1) N(5) H(52) 66.0(10) ?
C(2) C(3) O(3) H(31) -173.0(10) ?
C(2) C(3) C(4) H(4) -60.5(8) ?
C(3) C(2) O(2) H(21) -152.0(10) ?
C(3) C(2) C(1) H(11) 177.6(8) ?
C(3) C(2) C(1) H(12) -59.0(10) ?
C(3) C(4) O(4) H(41) 79.0(10) ?
C(3) C(4) C(5) H(5) 63.9(9) ?
C(4) C(3) O(3) H(31) 67.0(10) ?
C(4) C(3) C(2) H(2) 61.5(9) ?
C(4) C(5) N(5) H(51) 177.0(10) ?
C(4) C(5) N(5) H(52) -68.0(10) ?
C(4) C(5) C(6) H(62) 50.6(9) ?
C(4) C(5) C(6) H(63) -65.0(10) ?
C(5) N(5) C(1) H(11) -177.8(9) ?
C(5) N(5) C(1) H(12) 64.4(9) ?
C(5) C(4) O(4) H(41) -159.0(10) ?
C(5) C(4) C(3) H(3) -59.2(8) ?
C(5) C(6) O(6) H(61) -158.(2) ?
C(6) C(5) N(5) H(51) -60.0(10) ?
C(6) C(5) N(5) H(52) 54.0(10) ?
C(6) C(5) C(4) H(4) -57.3(9) ?
H(2) C(2) O(2) H(21) -33.(2) ?
H(2) C(2) C(1) H(11) 58.0(10) ?
H(2) C(2) C(1) H(12) -179.0(10) ?
H(2) C(2) C(3) H(3) 178.0(10) ?
H(3) C(3) O(3) H(31) -52.(2) ?
H(3) C(3) C(4) H(4) -179.0(10) ?
H(4) C(4) O(4) H(41) -39.0(10) ?
H(4) C(4) C(5) H(5) -178.0(10) ?
H(5) C(5) N(5) H(51) 55.0(10) ?
H(5) C(5) N(5) H(52) 169.(2) ?
H(5) C(5) C(6) H(62) 175.0(10) ?
H(5) C(5) C(6) H(63) 59.0(10) ?
H(11) C(1) N(5) H(51) 60.0(10) ?
H(11) C(1) N(5) H(52) -56.0(10) ?
H(12) C(1) N(5) H(51) -58.0(10) ?
H(12) C(1) N(5) H(52) -173.0(10) ?
H(61) O(6) C(6) H(62) -39.(2) ?
H(61) O(6) C(6) H(63) 84.(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 20009447
