#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/62/2006251.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_2006251
loop_
_publ_author_name
'Agianian, Bogos'
'Perrakis, Anastassis'
'Kanellopoulos, Panagiotis N.'
'Sheldrick, Bernard'
'Hamodrakas, Stavros J.'
_publ_section_title
;
 p-Nitrophenyl α-<small>D</small>-Mannopyranoside Ethanol
 Solvate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              811
_journal_page_last               814
_journal_paper_doi               10.1107/S0108270196015776
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C12 H15 N O8, C2 H6 O1'
_chemical_formula_sum            'C14 H21 N O9'
_chemical_formula_weight         347.32
_chemical_name_common            α-PNM
_chemical_name_systematic
;
 4'-nitrophenyl-α-D-mannopyranoside
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           SHELXL-93
_cell_angle_alpha                90.00
_cell_angle_beta                 92.94(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.290(3)
_cell_length_b                   7.926(3)
_cell_length_c                   14.654(4)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40
_cell_measurement_theta_min      20
_cell_volume                     845.6(5)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software'
_computing_molecular_graphics    'PLUTON (Spek, 1991); PLATON (Spek, 1990)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4 diffractometer'
_diffrn_measurement_method       'ω-2θ scan mode'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2321
_diffrn_reflns_theta_max         60
_diffrn_reflns_theta_min         3.02
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.989
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      1.33
_exptl_crystal_density_method    flotation
_exptl_crystal_description       Needle
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.357
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.084
_refine_ls_goodness_of_fit_obs   1.087
_refine_ls_hydrogen_treatment    'H atoms refined isotropically'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2133
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.096
_refine_ls_restrained_S_obs      1.082
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_obs          .0647
_refine_ls_shift/esd_max         -0.014
_refine_ls_shift/esd_mean        0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1379P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1767
_refine_ls_wR_factor_obs         .1702
_reflns_number_observed          2036
_reflns_number_total             2147
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            sk1000.cif
_cod_data_source_block           pnam
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.1379P)^2^] where P=(Fo^2^+2Fc^2^)/3' 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^(Fo^2^)+(0.1379P)^2^]
where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2006251
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 .3072(4) .9136(4) .2154(2) .0354(8) Uani d U 1 . O
O2 .1559(4) .5929(4) .3664(2) .0380(8) Uani d U 1 . O
H2A .1103(4) .6127(4) .4153(2) .046 Uiso calc R 1 . H
O3 -.1315(4) .8203(4) .3844(2) .0337(7) Uani d U 1 . O
H3A -.1176(6) .7868(8) .4372(5) .040 Uiso calc R 1 . H
O4 .0751(4) 1.1110(4) .4598(2) .0389(8) Uani d U 1 . O
H4A .0732(8) 1.1822(10) .4128(6) .047 Uiso calc R 1 . H
O5 .4325(4) .8472(4) .3614(2) .0285(7) Uani d U 1 . O
O6 .6577(4) 1.0710(5) .4663(2) .0422(8) Uani d U 1 . O
H6A .6679(6) 1.0579(4) .4112(4) .051 Uiso calc R 1 . H
O7 .9947(7) .9597(13) -.0209(4) .138(3) Uani d U 1 . O
O8 .7974(8) 1.0870(11) -.1056(4) .111(2) Uani d U 1 . O
N1 .8392(7) 1.0171(10) -.0360(3) .081(2) Uani d U 1 . N
C1 .3308(6) .7896(6) .2851(3) .0296(9) Uani d U 1 . C
H1 .3936(6) .6919(6) .2602(3) .028(3) Uiso calc R 1 . H
C2 .1372(6) .7360(6) .3093(3) .0292(9) Uani d U 1 . C
H21 .0670(6) .7043(6) .2530(3) .028(3) Uiso calc R 1 . H
C3 .0405(5) .8806(5) .3540(3) .0268(9) Uani d U 1 . C
H31 .0161(5) .9692(5) .3083(3) .028(3) Uiso calc R 1 . H
C4 .1576(5) .9552(5) .4338(3) .0248(9) Uani d U 1 . C
H41 .1601(5) .8766(5) .4855(3) .028(3) Uiso calc R 1 . H
C5 .3553(5) .9898(5) .4065(3) .0252(9) Uani d U 1 . C
H51 .3564(5) 1.0885(5) .3663(3) .028(3) Uiso calc R 1 . H
C6 .4777(5) 1.0213(6) .4898(3) .0338(10) Uani d U 1 . C
H61 .4247(5) 1.1091(6) .5262(3) .028(3) Uiso calc R 1 . H
H62 .4861(5) .9194(6) .5265(3) .028(3) Uiso calc R 1 . H
C7 .4479(6) .9372(6) .1583(3) .0353(10) Uani d U 1 . C
C8 .4015(7) 1.0274(8) .0793(3) .0486(13) Uani d U 1 . C
H8 .2833(7) 1.0700(8) .0694(3) .028(3) Uiso calc R 1 . H
C9 .5313(7) 1.0534(8) .0158(4) .0554(15) Uani d U 1 . C
H9 .5012(7) 1.1124(8) -.0377(4) .028(3) Uiso calc R 1 . H
C10 .7075(7) .9907(8) .0326(3) .0489(13) Uani d U 1 . C
C11 .7558(7) .9059(8) .1111(3) .0470(13) Uani d U 1 . C
H11 .8753(7) .8666(8) .1211(3) .028(3) Uiso calc R 1 . H
C12 .6254(6) .8776(7) .1770(3) .0396(11) Uani d U 1 . C
H12 .6568(6) .8210(7) .2312(3) .028(3) Uiso calc R 1 . H
O50 -.048(3) .321(2) .3270(10) .063(2) Uiso d PD .43(2) 1 O
C51 -.178(4) .282(2) .261(2) .081(4) Uiso d PD .43(2) 1 C
C52 -.305(3) .425(3) .232(2) .097(5) Uiso d PD .43(2) 1 C
O60 .013(4) .308(3) .299(2) .063(2) Uiso d PD .23(2) 2 O
C61 -.130(4) .318(6) .237(2) .081(4) Uiso d PD .23(2) 2 C
C62 -.312(4) .384(7) .273(4) .097(5) Uiso d PD .23(2) 2 C
O70 -.096(3) .352(2) .3460(10) .063(2) Uiso d PD .35(2) 3 O
C71 -.242(4) .311(4) .289(2) .081(4) Uiso d PD .35(2) 3 C
C72 -.261(4) .395(4) .198(2) .097(5) Uiso d PD .35(2) 3 C
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_publ_flag
C7 O1 C1 117.8(3) yes
C2 O2 H2A 109.5(2) ?
C3 O3 H3A 109.5(2) ?
C4 O4 H4A 109.3(3) ?
C1 O5 C5 115.0(3) yes
C6 O6 H6A 109.4(3) ?
O8 N1 O7 121.4(5) no
O8 N1 C10 121.1(5) no
O7 N1 C10 117.5(5) no
O5 C1 O1 113.0(3) yes
O5 C1 C2 111.4(3) yes
O1 C1 C2 106.2(3) yes
O5 C1 H1 108.7(2) ?
O1 C1 H1 108.7(2) ?
C2 C1 H1 108.7(2) ?
O2 C2 C3 112.6(3) yes
O2 C2 C1 107.3(3) yes
C3 C2 C1 110.2(4) yes
O2 C2 H21 108.9(2) ?
C3 C2 H21 108.9(2) ?
C1 C2 H21 108.9(2) ?
O3 C3 C2 108.5(3) yes
O3 C3 C4 110.7(3) yes
C2 C3 C4 111.7(3) yes
O3 C3 H31 108.6(2) ?
C2 C3 H31 108.6(2) ?
C4 C3 H31 108.6(2) ?
O4 C4 C3 108.1(3) yes
O4 C4 C5 109.1(3) yes
C3 C4 C5 111.3(3) yes
O4 C4 H41 109.4(2) ?
C3 C4 H41 109.4(2) ?
C5 C4 H41 109.4(2) ?
O5 C5 C6 106.0(3) yes
O5 C5 C4 111.9(3) yes
C6 C5 C4 110.2(3) yes
O5 C5 H51 109.6(2) ?
C6 C5 H51 109.6(2) ?
C4 C5 H51 109.6(2) ?
O6 C6 C5 111.5(3) yes
O6 C6 H61 109.3(2) ?
C5 C6 H61 109.3(2) ?
O6 C6 H62 109.3(2) ?
C5 C6 H62 109.3(2) ?
H61 C6 H62 108.0 ?
O1 C7 C8 114.9(4) no
O1 C7 C12 123.5(4) no
C8 C7 C12 121.6(4) no
C9 C8 C7 119.7(4) no
C9 C8 H8 120.2(3) ?
C7 C8 H8 120.2(3) ?
C8 C9 C10 119.3(5) no
C8 C9 H9 120.4(3) ?
C10 C9 H9 120.4(3) ?
C11 C10 C9 121.5(4) no
C11 C10 N1 120.5(5) no
C9 C10 N1 118.0(5) no
C10 C11 C12 120.2(5) no
C10 C11 H11 119.9(3) ?
C12 C11 H11 119.9(3) ?
C7 C12 C11 117.7(4) no
C7 C12 H12 121.2(3) ?
C11 C12 H12 121.2(3) ?
O50 C51 C52 115.4(16) ?
O60 C61 C62 116.(2) ?
O70 C71 C72 118.3(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.369(6) yes
O1 C1 . 1.422(5) yes
O2 C2 . 1.412(6) yes
O2 H2A . .82 ?
O3 C3 . 1.434(5) yes
O3 H3A . .82 ?
O4 C4 . 1.434(5) yes
O4 H4A . .890(3) ?
O5 C1 . 1.387(5) yes
O5 C5 . 1.438(5) yes
O6 C6 . 1.429(5) yes
O6 H6A . .822(3) ?
O7 N1 . 1.231(8) yes
O8 N1 . 1.188(7) yes
N1 C10 . 1.440(7) yes
C1 C2 . 1.533(6) yes
C1 H1 . .98 ?
C2 C3 . 1.512(6) yes
C2 H21 . .98 ?
C3 C4 . 1.530(6) yes
C3 H31 . .98 ?
C4 C5 . 1.540(5) yes
C4 H41 . .98 ?
C5 C6 . 1.496(6) yes
C5 H51 . .98 ?
C6 H61 . .97 ?
C6 H62 . .97 ?
C7 C8 . 1.387(6) no
C7 C12 . 1.392(7) no
C8 C9 . 1.376(8) no
C8 H8 . .93 ?
C9 C10 . 1.388(8) no
C9 H9 . .93 ?
C10 C11 . 1.363(7) no
C11 C12 . 1.408(7) no
C11 H11 . .93 ?
C12 H12 . .93 ?
O50 C51 . 1.36(2) ?
C51 C52 . 1.51(2) ?
O60 C61 . 1.35(2) ?
C61 C62 . 1.54(3) ?
O70 C71 . 1.35(2) ?
C71 C72 . 1.49(2) ?
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
C5 O5 C1 O1 60.2(4) ?
C5 O5 C1 C2 -59.3(4) ?
C7 O1 C1 O5 81.4(4) yes
C7 O1 C1 C2 -156.1(4) yes
O5 C1 C2 O2 -66.5(4) ?
O1 C1 C2 O2 170.0(3) ?
O5 C1 C2 C3 56.4(4) ?
O1 C1 C2 C3 -67.1(4) ?
O2 C2 C3 O3 -54.1(4) ?
C1 C2 C3 O3 -173.9(3) ?
O2 C2 C3 C4 68.2(4) ?
C1 C2 C3 C4 -51.6(4) ?
O3 C3 C4 O4 -70.8(4) ?
C2 C3 C4 O4 168.2(3) ?
O3 C3 C4 C5 169.4(3) ?
C2 C3 C4 C5 48.4(4) ?
C1 O5 C5 C6 175.6(3) ?
C1 O5 C5 C4 55.5(4) ?
O4 C4 C5 O5 -167.6(3) ?
C3 C4 C5 O5 -48.4(4) ?
O4 C4 C5 C6 74.8(4) ?
C3 C4 C5 C6 -166.0(3) ?
O5 C5 C6 O6 64.8(4) yes
C4 C5 C6 O6 -173.9(4) yes
C1 O1 C7 C8 164.8(4) yes
C1 O1 C7 C12 -15.6(6) yes
O1 C7 C8 C9 -177.9(5) ?
C12 C7 C8 C9 2.6(8) ?
C7 C8 C9 C10 -0.8(9) ?
C8 C9 C10 C11 -0.9(10) ?
C8 C9 C10 N1 178.8(6) ?
O8 N1 C10 C11 178.1(7) yes
O7 N1 C10 C11 0.4(11) yes
O8 N1 C10 C9 -1.6(11) yes
O7 N1 C10 C9 -179.3(8) yes
C9 C10 C11 C12 1.0(9) ?
N1 C10 C11 C12 -178.7(6) ?
O1 C7 C12 C11 178.0(4) ?
C8 C7 C12 C11 -2.5(8) ?
C10 C11 C12 C7 0.7(8) ?
