#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/13/2011338.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_2011338
loop_
_publ_author_name
'Gzella, Andrzej'
'Wrzeciono, Urszula'
'Pöppel, Wolfram'
_publ_section_title
;
 Azole. 44. Über Morpholinonitroimidazolderivate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1161
_journal_page_last               1163
_journal_paper_doi               10.1107/S0108270100008635
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C10 H15 Cl N4 O4'
_chemical_formula_sum            'C10 H15 Cl N4 O4'
_chemical_formula_weight         290.71
_chemical_name_systematic
;
3-Chloro-1-(5-morpholinyl-4-nitroimidazol-1-yl)propan-2-ol
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL97
_cell_angle_alpha                91.101(9)
_cell_angle_beta                 101.026(10)
_cell_angle_gamma                101.940(10)
_cell_formula_units_Z            2
_cell_length_a                   6.5036(8)
_cell_length_b                   7.8493(9)
_cell_length_c                   12.9757(14)
_cell_measurement_reflns_used    43
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      11.3
_cell_volume                     634.91(13)
_computing_cell_refinement       'Kuma KM-4 Software'
_computing_data_collection       'Kuma KM-4 Software (Kuma Diffraction, 1991)'
_computing_data_reduction        'Kuma KM-4 Software'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .950
_diffrn_measured_fraction_theta_max .950
_diffrn_measurement_device_type  'Kuma Diffraction KM-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  .022
_diffrn_reflns_av_sigmaI/netI    .015
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2386
_diffrn_reflns_theta_full        70.04
_diffrn_reflns_theta_max         70.04
_diffrn_reflns_theta_min         3.48
_diffrn_standards_decay_%        3.8
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.853
_exptl_absorpt_correction_T_max  .867
_exptl_absorpt_correction_T_min  .440
_exptl_absorpt_correction_type   \y-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             304
_exptl_crystal_size_max          .38
_exptl_crystal_size_mid          .27
_exptl_crystal_size_min          .05
_refine_diff_density_max         .36
_refine_diff_density_min         -.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2281
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          .048
_refine_ls_R_factor_gt           .041
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0695P)²+0.2622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .122
_reflns_number_gt                2036
_reflns_number_total             2281
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jz1415.cif
_cod_data_source_block           III
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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               2011338
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 .8161(2) .51309(19) .14522(12) .0354(3) Uani d . 1 . . N
C2 .7643(3) .5726(2) .04814(15) .0379(4) Uani d . 1 . . C
H2A .7488 .6863 .0368 .046 Uiso calc . 1 . . H
N3 .7385(2) .4537(2) -.02739(12) .0396(4) Uani d . 1 . . N
C4 .7703(3) .3077(2) .02411(14) .0364(4) Uani d . 1 . . C
C5 .8218(3) .3398(2) .13179(14) .0338(4) Uani d . 1 . . C
C6 .8466(3) .6089(2) .24612(15) .0386(4) Uani d . 1 . . C
H6A .9424 .7213 .2456 .046 Uiso calc . 1 . . H
H6B .9132 .5448 .3014 .046 Uiso calc . 1 . . H
C7 .6325(3) .6369(2) .26959(14) .0387(4) Uani d . 1 . . C
H7A .5964 .7392 .2344 .046 Uiso calc . 1 . . H
C8 .6605(4) .6696(3) .38694(16) .0502(5) Uani d . 1 . . C
H8A .7863 .7616 .4119 .060 Uiso calc . 1 . . H
H8B .6834 .5647 .4216 .060 Uiso calc . 1 . . H
Cl9 .43074(12) .73111(11) .42040(5) .0762(3) Uani d . 1 . . Cl
O10 .4646(2) .49088(19) .23518(12) .0462(4) Uani d . 1 . . O
H10A .389(5) .512(4) .175(2) .071(9) Uiso d . 1 . . H
N11 .7442(3) .1472(2) -.03436(13) .0439(4) Uani d . 1 . . N
O12 .7421(3) .0135(2) .01360(14) .0599(4) Uani d . 1 . . O
O13 .7223(3) .1494(2) -.13030(12) .0661(5) Uani d . 1 . . O
N14 .8900(3) .2497(2) .21725(12) .0368(4) Uani d . 1 . . N
C15 .7373(3) .1714(3) .28089(16) .0436(5) Uani d . 1 . . C
H15A .6553 .0594 .2483 .052 Uiso calc . 1 . . H
H15B .6384 .2465 .2867 .052 Uiso calc . 1 . . H
C16 .8614(4) .1479(3) .38845(19) .0571(6) Uani d . 1 . . C
H16A .9332 .2613 .4226 .068 Uiso calc . 1 . . H
H16B .7629 .0911 .4310 .068 Uiso calc . 1 . . H
O17 1.0168(3) .0456(2) .38198(13) .0600(5) Uani d . 1 . . O
C18 1.1640(4) .1254(3) .32027(18) .0507(5) Uani d . 1 . . C
H18A 1.2689 .0547 .3176 .061 Uiso calc . 1 . . H
H18B 1.2396 .2391 .3528 .061 Uiso calc . 1 . . H
C19 1.0502(3) .1458(3) .21028(16) .0439(5) Uani d . 1 . . C
H19A 1.1520 .2039 .1698 .053 Uiso calc . 1 . . H
H19B .9809 .0322 .1756 .053 Uiso calc . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .3639 .7018 '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
C2 N1 C5 107.45(15) yes
C2 N1 C6 127.10(15) ?
C5 N1 C6 125.33(15) ?
N3 C2 N1 112.92(16) yes
C2 N3 C4 103.95(15) yes
N3 C4 C5 112.18(16) yes
N3 C4 N11 119.78(16) ?
C5 C4 N11 128.02(17) ?
N1 C5 N14 120.03(16) ?
N1 C5 C4 103.47(15) yes
N14 C5 C4 136.16(17) ?
N1 C6 C7 111.54(15) ?
O10 C7 C8 109.33(17) ?
O10 C7 C6 111.85(15) ?
C8 C7 C6 108.05(16) ?
C7 C8 Cl9 111.27(15) ?
C7 O10 H10A 108.8(19) ?
O13 N11 O12 123.55(18) ?
O13 N11 C4 118.07(18) ?
O12 N11 C4 118.38(17) ?
C5 N14 C15 119.37(15) ?
C5 N14 C19 118.71(15) ?
C15 N14 C19 112.40(14) ?
N14 C15 C16 108.18(17) ?
O17 C16 C15 111.35(18) ?
C18 O17 C16 110.78(16) ?
O17 C18 C19 111.02(18) ?
N14 C19 C18 108.05(16) ?
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
N1 C2 . 1.358(2) yes
N1 C5 . 1.377(2) yes
N1 C6 . 1.456(2) ?
C2 N3 . 1.303(3) yes
N3 C4 . 1.370(2) yes
C4 C5 . 1.379(3) yes
C4 N11 . 1.421(2) yes
C5 N14 . 1.378(2) yes
C6 C7 . 1.538(3) ?
C7 O10 . 1.407(2) ?
C7 C8 . 1.509(3) ?
C8 Cl9 . 1.787(2) yes
O10 H10A . .88(3) ?
N11 O13 . 1.227(2) ?
N11 O12 . 1.229(2) ?
N14 C15 . 1.458(2) ?
N14 C19 . 1.463(2) ?
C15 C16 . 1.508(3) ?
C16 O17 . 1.427(3) ?
O17 C18 . 1.419(3) ?
C18 C19 . 1.505(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O10 H10A N3 2_665 .88(3) 1.98(3) 2.850(2) 169(3) yes
C7 H7A O13 2_665 .98 2.57 3.396(2) 142 yes
C8 H8A O17 1_565 .97 2.50 3.364(3) 149 yes
C15 H15B O10 . .97 2.46 3.359(2) 154 yes
C19 H19B O12 . .97 2.34 2.947(3) 120 yes
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
C5 N1 C2 N3 -.9(2)
C6 N1 C2 N3 -177.08(17)
N1 C2 N3 C4 1.6(2)
C2 N3 C4 C5 -1.7(2)
C2 N3 C4 N11 176.94(17)
C2 N1 C5 N14 174.00(16)
C6 N1 C5 N14 -9.7(3)
C2 N1 C5 C4 -.3(2)
C6 N1 C5 C4 176.04(16)
N3 C4 C5 N1 1.3(2)
N11 C4 C5 N1 -177.31(18)
N3 C4 C5 N14 -171.6(2)
N11 C4 C5 N14 9.9(4)
C2 N1 C6 C7 71.6(2)
C5 N1 C6 C7 -103.9(2)
N1 C6 C7 O10 37.7(2)
N1 C6 C7 C8 158.05(16)
O10 C7 C8 Cl9 -65.47(19)
C6 C7 C8 Cl9 172.58(14)
N3 C4 N11 O13 9.8(3)
C5 C4 N11 O13 -171.78(19)
N3 C4 N11 O12 -169.34(17)
C5 C4 N11 O12 9.1(3)
N1 C5 N14 C15 85.0(2)
C4 C5 N14 C15 -103.1(3)
N1 C5 N14 C19 -131.23(19)
C4 C5 N14 C19 40.7(3)
C5 N14 C15 C16 -157.27(18)
C19 N14 C15 C16 56.8(2)
N14 C15 C16 O17 -56.5(2)
C15 C16 O17 C18 59.1(3)
C16 O17 C18 C19 -59.8(3)
C5 N14 C19 C18 156.31(18)
C15 N14 C19 C18 -57.5(2)
O17 C18 C19 N14 57.9(2)
