#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/13/2011320.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_2011320
loop_
_publ_author_name
'Lah, Nina'
'Leban, Ivan'
'Majcen-Le Maréchal, Alenka'
'Le Grel, Philippe'
'Robert, Albert'
'Sieler, Joachim'
'Giester, Gerald'
_publ_section_title
;
 From α-carbamoyl-α-cyanooxiranes to 3-halogenopyruvamides
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1164
_journal_page_last               1167
_journal_paper_doi               10.1107/S0108270100008623
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C10 H7 Cl N2 O2'
_chemical_formula_sum            'C10 H7 Cl N2 O2'
_chemical_formula_weight         222.63
_chemical_name_systematic
;
 3-(4-chlorophenyl)-2-cyano-2,3-epoxypropanamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELX-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.540(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9992(8)
_cell_length_b                   12.694(3)
_cell_length_c                   16.442(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     1041.4(4)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe, 1992)'
_computing_data_reduction        'REDU4 (Stoe, 1992)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device_type  STADI4(STOE)
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0251
_diffrn_reflns_av_sigmaI/netI    .0203
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3492
_diffrn_reflns_theta_full        29.15
_diffrn_reflns_theta_max         28.0
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        .8
_diffrn_standards_interval_count 300
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .346
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             456
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .25
_refine_diff_density_max         .288
_refine_diff_density_min         -.337
_refine_ls_extinction_coef       .061(6)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2533
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          .0683
_refine_ls_R_factor_gt           .0478
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0811P)²+0.2445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1515
_reflns_number_gt                1852
_reflns_number_total             2533
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd1105.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_hbond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times).

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^)+(0.0811P)^2^+0.2445P] 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^)+(0.0811P)^2^+0.2445P] 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/c'
_cod_database_code               2011320
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y-1/2, -z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_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 .7265(3) .03484(16) -.41529(10) .0612(5) Uani d . 1 . . N
H1 .7222 .0306 -.4676 .068(7) Uiso calc R 1 . . H
H2 .8713 .0541 -.3884 .083(8) Uiso calc R 1 . . H
C1 .5113(3) .01177(14) -.37641(11) .0460(4) Uani d . 1 . . C
O1 .2951(2) -.01638(12) -.40846(8) .0591(4) Uani d . 1 . . O
C2 .5379(3) .02381(14) -.28500(10) .0458(4) Uani d . 1 . . C
C10 .3935(4) -.05536(15) -.24065(11) .0534(4) Uani d . 1 . . C
N2 .2806(5) -.11797(15) -.20777(13) .0795(6) Uani d . 1 . . N
C3 .5770(4) .13093(15) -.24897(12) .0521(4) Uani d . 1 . . C
H3 .5857 .1889 -.2882 .065(6) Uiso calc R 1 . . H
O2 .7912(2) .05587(13) -.24926(8) .0618(4) Uani d . 1 . . O
C4 .4738(4) .15929(14) -.16894(11) .0508(4) Uani d . 1 . . C
C5 .2670(4) .23174(16) -.16634(13) .0577(5) Uani d . 1 . . C
H5 .1976 .2631 -.2142 .054(5) Uiso calc R 1 . . H
C6 .1631(4) .25776(17) -.09257(15) .0644(5) Uani d . 1 . . C
H6 .0219 .3052 -.0907 .092(8) Uiso calc R 1 . . H
C7 .2730(4) .21197(17) -.02199(13) .0607(5) Uani d . 1 . . C
C8 .4810(5) .14142(18) -.02315(12) .0642(5) Uani d . 1 . . C
H8 .5532 .1118 .0251 .081(7) Uiso calc R 1 . . H
C9 .5820(4) .11482(17) -.09691(12) .0601(5) Uani d . 1 . . C
H9 .7226 .0670 -.0983 .075(7) Uiso calc R 1 . . H
Cl .13798(15) .24047(7) .07086(4) .0936(3) Uani d . 1 . . Cl
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
N1 .0338(7) .0949(13) .0556(9) -.0122(7) .0080(6) -.0042(8)
C1 .0327(7) .0515(9) .0544(9) .0011(6) .0065(6) -.0012(7)
O1 .0327(6) .0863(10) .0589(7) -.0083(6) .0072(5) -.0086(7)
C2 .0344(7) .0494(9) .0537(9) .0004(6) .0045(6) .0023(7)
C10 .0597(10) .0432(9) .0586(10) .0059(8) .0140(8) .0004(8)
N2 .1039(15) .0507(10) .0877(13) -.0041(10) .0376(11) .0039(9)
C3 .0487(9) .0516(10) .0560(10) -.0070(7) .0028(7) .0024(8)
O2 .0366(6) .0857(10) .0626(7) .0000(6) -.0006(5) -.0085(7)
C4 .0502(9) .0456(9) .0567(10) -.0089(7) .0044(7) -.0022(7)
C5 .0561(10) .0504(10) .0665(11) -.0034(8) .0026(8) .0027(9)
C6 .0577(11) .0549(11) .0815(14) .0004(9) .0117(9) -.0070(10)
C7 .0627(11) .0571(11) .0635(11) -.0100(9) .0119(9) -.0127(9)
C8 .0729(13) .0637(12) .0555(11) -.0009(10) .0009(9) -.0017(9)
C9 .0600(10) .0581(11) .0618(11) .0051(9) .0017(8) -.0028(9)
Cl .0949(5) .1114(6) .0768(4) .0013(4) .0235(3) -.0278(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 '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 .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .1585 '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
C1 N1 H1 120.0 ?
C1 N1 H2 120.0 ?
H1 N1 H2 120.0 ?
O1 C1 N1 125.49(17) yes
O1 C1 C2 118.63(14) yes
N1 C1 C2 115.87(15) yes
O2 C2 C10 116.49(15) yes
O2 C2 C3 58.89(11) yes
C10 C2 C3 119.11(15) yes
O2 C2 C1 117.53(13) yes
C10 C2 C1 114.35(15) yes
C3 C2 C1 119.31(15) yes
N2 C10 C2 178.5(2) yes
O2 C3 C4 117.63(16) yes
O2 C3 C2 58.15(11) yes
C4 C3 C2 121.88(16) yes
O2 C3 H3 115.7 ?
C4 C3 H3 115.7 ?
C2 C3 H3 115.7 ?
C2 O2 C3 62.96(11) yes
C5 C4 C9 119.63(18) yes
C5 C4 C3 119.20(17) yes
C9 C4 C3 121.16(18) yes
C4 C5 C6 120.31(19) yes
C4 C5 H5 119.8 ?
C6 C5 H5 119.8 ?
C7 C6 C5 118.9(2) yes
C7 C6 H6 120.6 ?
C5 C6 H6 120.6 ?
C8 C7 C6 121.66(19) yes
C8 C7 Cl 118.78(17) yes
C6 C7 Cl 119.51(17) yes
C7 C8 C9 119.3(2) yes
C7 C8 H8 120.4 ?
C9 C8 H8 120.4 ?
C8 C9 C4 120.2(2) yes
C8 C9 H9 119.9 ?
C4 C9 H9 119.9 ?
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 C1 . 1.318(2) yes
N1 H1 . .8600 ?
N1 H2 . .8600 ?
C1 O1 . 1.226(2) yes
C1 C2 . 1.508(2) yes
C2 O2 . 1.422(2) yes
C2 C10 . 1.459(2) yes
C2 C3 . 1.491(3) yes
C10 N2 . 1.132(3) yes
C3 O2 . 1.434(2) yes
C3 C4 . 1.487(3) yes
C3 H3 . .9800 ?
C4 C5 . 1.386(3) yes
C4 C9 . 1.391(3) yes
C5 C6 . 1.389(3) yes
C5 H5 . .9300 ?
C6 C7 . 1.381(3) yes
C6 H6 . .9300 ?
C7 C8 . 1.373(3) yes
C7 Cl . 1.745(2) yes
C8 C9 . 1.384(3) yes
C8 H8 . .9300 ?
C9 H9 . .9300 ?
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
N1 H2 O2 . .86 2.35 2.742(2) 108.4 ?
N1 H2 O1 1_655 .86 2.34 2.911(2) 124.0 y
N1 H1 O1 3_654 .86 2.04 2.903(2) 178.2 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21135581
