#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006251.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, B.'
'Perrakis, A.'
'Kanellopoulos, P. N.'
'Sheldrick, B.'
'Hamodrakas, S. J.'
_publ_section_title
;
 <i>p</i>-Nitrophenyl \a-<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_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            \a-PNM
_chemical_name_systematic
;
 4'-nitrophenyl-\a-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       '\w-2\q 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          0.0647
_refine_ls_shift/esd_max         -0.014
_refine_ls_shift/esd_mean        0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.1379P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1767
_refine_ls_wR_factor_obs         0.1702
_reflns_number_observed          2036
_reflns_number_total             2147
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    sk1000.cif
_[local]_cod_data_source_block   pnam
_[local]_cod_cif_authors_sg_H-M  'P 21'
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2006251
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
O1 0.025(2) 0.048(2) 0.034(2) 0.0031(14) 0.0092(12) 0.0073(14)
O2 0.035(2) 0.039(2) 0.041(2) 0.0004(14) 0.0047(14) 0.0043(14)
O3 0.0106(13) 0.047(2) 0.043(2) -0.0049(12) 0.0020(11) 0.003(2)
O4 0.024(2) 0.041(2) 0.052(2) 0.0063(13) 0.0079(13) -0.0112(15)
O5 0.0158(13) 0.038(2) 0.0321(15) 0.0037(12) 0.0037(11) -0.0036(12)
O6 0.017(2) 0.056(2) 0.054(2) -0.0064(14) 0.0034(13) -0.006(2)
O7 0.035(2) 0.294(10) 0.088(4) 0.017(4) 0.021(2) 0.062(5)
O8 0.079(3) 0.191(7) 0.066(3) 0.020(4) 0.033(3) 0.064(4)
N1 0.050(3) 0.142(6) 0.051(3) -0.001(3) 0.018(2) 0.031(4)
C1 0.025(2) 0.037(2) 0.027(2) 0.003(2) 0.006(2) -0.001(2)
C2 0.022(2) 0.037(2) 0.029(2) -0.001(2) -0.001(2) 0.001(2)
C3 0.010(2) 0.038(2) 0.032(2) -0.005(2) 0.000(2) 0.004(2)
C4 0.015(2) 0.031(2) 0.029(2) 0.003(2) 0.005(2) 0.000(2)
C5 0.013(2) 0.033(2) 0.030(2) 0.000(2) 0.007(2) 0.001(2)
C6 0.014(2) 0.045(3) 0.043(2) -0.008(2) 0.003(2) -0.005(2)
C7 0.029(2) 0.044(3) 0.034(2) -0.004(2) 0.003(2) 0.002(2)
C8 0.033(3) 0.076(4) 0.037(3) 0.007(3) 0.005(2) 0.018(3)
C9 0.040(3) 0.080(4) 0.046(3) 0.001(3) 0.000(2) 0.031(3)
C10 0.035(2) 0.074(4) 0.038(2) -0.012(3) 0.008(2) 0.010(3)
C11 0.025(2) 0.078(4) 0.038(2) -0.011(3) 0.005(2) 0.002(3)
C12 0.027(2) 0.061(3) 0.032(2) 0.000(2) 0.003(2) 0.006(2)
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 0.3072(4) 0.9136(4) 0.2154(2) 0.0354(8) Uani d U 1 . O
O2 0.1559(4) 0.5929(4) 0.3664(2) 0.0380(8) Uani d U 1 . O
H2A 0.1103(4) 0.6127(4) 0.4153(2) 0.046 Uiso calc R 1 . H
O3 -0.1315(4) 0.8203(4) 0.3844(2) 0.0337(7) Uani d U 1 . O
H3A -0.1176(6) 0.7868(8) 0.4372(5) 0.040 Uiso calc R 1 . H
O4 0.0751(4) 1.1110(4) 0.4598(2) 0.0389(8) Uani d U 1 . O
H4A 0.0732(8) 1.1822(10) 0.4128(6) 0.047 Uiso calc R 1 . H
O5 0.4325(4) 0.8472(4) 0.3614(2) 0.0285(7) Uani d U 1 . O
O6 0.6577(4) 1.0710(5) 0.4663(2) 0.0422(8) Uani d U 1 . O
H6A 0.6679(6) 1.0579(4) 0.4112(4) 0.051 Uiso calc R 1 . H
O7 0.9947(7) 0.9597(13) -0.0209(4) 0.138(3) Uani d U 1 . O
O8 0.7974(8) 1.0870(11) -0.1056(4) 0.111(2) Uani d U 1 . O
N1 0.8392(7) 1.0171(10) -0.0360(3) 0.081(2) Uani d U 1 . N
C1 0.3308(6) 0.7896(6) 0.2851(3) 0.0296(9) Uani d U 1 . C
H1 0.3936(6) 0.6919(6) 0.2602(3) 0.028(3) Uiso calc R 1 . H
C2 0.1372(6) 0.7360(6) 0.3093(3) 0.0292(9) Uani d U 1 . C
H21 0.0670(6) 0.7043(6) 0.2530(3) 0.028(3) Uiso calc R 1 . H
C3 0.0405(5) 0.8806(5) 0.3540(3) 0.0268(9) Uani d U 1 . C
H31 0.0161(5) 0.9692(5) 0.3083(3) 0.028(3) Uiso calc R 1 . H
C4 0.1576(5) 0.9552(5) 0.4338(3) 0.0248(9) Uani d U 1 . C
H41 0.1601(5) 0.8766(5) 0.4855(3) 0.028(3) Uiso calc R 1 . H
C5 0.3553(5) 0.9898(5) 0.4065(3) 0.0252(9) Uani d U 1 . C
H51 0.3564(5) 1.0885(5) 0.3663(3) 0.028(3) Uiso calc R 1 . H
C6 0.4777(5) 1.0213(6) 0.4898(3) 0.0338(10) Uani d U 1 . C
H61 0.4247(5) 1.1091(6) 0.5262(3) 0.028(3) Uiso calc R 1 . H
H62 0.4861(5) 0.9194(6) 0.5265(3) 0.028(3) Uiso calc R 1 . H
C7 0.4479(6) 0.9372(6) 0.1583(3) 0.0353(10) Uani d U 1 . C
C8 0.4015(7) 1.0274(8) 0.0793(3) 0.0486(13) Uani d U 1 . C
H8 0.2833(7) 1.0700(8) 0.0694(3) 0.028(3) Uiso calc R 1 . H
C9 0.5313(7) 1.0534(8) 0.0158(4) 0.0554(15) Uani d U 1 . C
H9 0.5012(7) 1.1124(8) -0.0377(4) 0.028(3) Uiso calc R 1 . H
C10 0.7075(7) 0.9907(8) 0.0326(3) 0.0489(13) Uani d U 1 . C
C11 0.7558(7) 0.9059(8) 0.1111(3) 0.0470(13) Uani d U 1 . C
H11 0.8753(7) 0.8666(8) 0.1211(3) 0.028(3) Uiso calc R 1 . H
C12 0.6254(6) 0.8776(7) 0.1770(3) 0.0396(11) Uani d U 1 . C
H12 0.6568(6) 0.8210(7) 0.2312(3) 0.028(3) Uiso calc R 1 . H
O50 -0.048(3) 0.321(2) 0.3270(10) 0.063(2) Uiso d PD 0.43(2) 1 O
C51 -0.178(4) 0.282(2) 0.261(2) 0.081(4) Uiso d PD 0.43(2) 1 C
C52 -0.305(3) 0.425(3) 0.232(2) 0.097(5) Uiso d PD 0.43(2) 1 C
O60 0.013(4) 0.308(3) 0.299(2) 0.063(2) Uiso d PD 0.23(2) 2 O
C61 -0.130(4) 0.318(6) 0.237(2) 0.081(4) Uiso d PD 0.23(2) 2 C
C62 -0.312(4) 0.384(7) 0.273(4) 0.097(5) Uiso d PD 0.23(2) 2 C
O70 -0.096(3) 0.352(2) 0.3460(10) 0.063(2) Uiso d PD 0.35(2) 3 O
C71 -0.242(4) 0.311(4) 0.289(2) 0.081(4) Uiso d PD 0.35(2) 3 C
C72 -0.261(4) 0.395(4) 0.198(2) 0.097(5) Uiso d PD 0.35(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_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 0.82 ?
O3 C3 1.434(5) yes
O3 H3A 0.82 ?
O4 C4 1.434(5) yes
O4 H4A 0.890(3) ?
O5 C1 1.387(5) yes
O5 C5 1.438(5) yes
O6 C6 1.429(5) yes
O6 H6A 0.822(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 0.98 ?
C2 C3 1.512(6) yes
C2 H21 0.98 ?
C3 C4 1.530(6) yes
C3 H31 0.98 ?
C4 C5 1.540(5) yes
C4 H41 0.98 ?
C5 C6 1.496(6) yes
C5 H51 0.98 ?
C6 H61 0.97 ?
C6 H62 0.97 ?
C7 C8 1.387(6) no
C7 C12 1.392(7) no
C8 C9 1.376(8) no
C8 H8 0.93 ?
C9 C10 1.388(8) no
C9 H9 0.93 ?
C10 C11 1.363(7) no
C11 C12 1.408(7) no
C11 H11 0.93 ?
C12 H12 0.93 ?
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) ?