#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/21/2012120.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_2012120
loop_
_publ_author_name
'Borbulevych, Oleg Ya.'
'Golding, Igor R.'
'Shchegolikhin, Alexander N.'
'Klemenkova, Zinaida S.'
'Antipin, Mikhail Yu.'
_publ_section_title
;
 Conformational polymorphs of
 22-cyano-N-methyl-5-phenylpent-2-en-4-ynamide
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              996
_journal_page_last               998
_journal_paper_doi               10.1107/S010827010100909X
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C13 H10 N2 O'
_chemical_formula_sum            'C13 H10 N2 O'
_chemical_formula_weight         210.23
_chemical_melting_point          384
_chemical_name_systematic
;
2-cyano-5-phenyl-pent-2-en-4-ynoic acid N-methylamide form (II)
;
_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           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 97.29(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.652(12)
_cell_length_b                   9.728(7)
_cell_length_c                   10.269(5)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      10
_cell_volume                     2245(2)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .981
_diffrn_measured_fraction_theta_max .981
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'θ/2θ scans'
_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  .079
_diffrn_reflns_av_sigmaI/netI    .074
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4929
_diffrn_reflns_theta_full        27.01
_diffrn_reflns_theta_max         27.01
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        3.4
_diffrn_standards_interval_count 90
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    .081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             880
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_refine_diff_density_max         .16
_refine_diff_density_min         -.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .959
_refine_ls_R_factor_all          .165
_refine_ls_R_factor_gt           .052
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.091P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .169
_reflns_number_gt                2134
_reflns_number_total             4810
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1452.cif
_cod_data_source_block           II
_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 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2012120
_cod_database_fobs_code          2012120
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
O1 .51989(9) .1326(2) .65637(18) .0714(6) Uani d . 1 . . O
N1 .40660(13) .5274(3) .5243(3) .0824(8) Uani d . 1 . . N
N2 .52030(9) .3542(2) .72239(19) .0545(6) Uani d . 1 . . N
H2 .5022 .4320 .7122 .065 Uiso calc R 1 . . H
C1 .50077(11) .2491(3) .6456(2) .0490(6) Uani d . 1 . . C
C2 .45142(11) .2854(3) .5377(2) .0476(6) Uani d . 1 . . C
C3 .43153(11) .1924(3) .4453(2) .0555(7) Uani d . 1 . . C
H3 .4479 .1046 .4507 .067 Uiso calc R 1 . . H
C4 .38672(12) .2227(3) .3404(2) .0536(7) Uani d . 1 . . C
C5 .34816(12) .2549(3) .2550(2) .0519(7) Uani d . 1 . . C
C6 .42675(12) .4201(3) .5295(2) .0558(7) Uani d . 1 . . C
C7 .30001(11) .2962(3) .1603(2) .0462(6) Uani d . 1 . . C
C8 .27396(13) .4228(3) .1721(3) .0664(8) Uani d . 1 . . C
H8 .2894 .4825 .2387 .080 Uiso calc R 1 . . H
C9 .22506(14) .4615(4) .0858(3) .0778(9) Uani d . 1 . . C
H9 .2074 .5468 .0946 .093 Uiso calc R 1 . . H
C10 .20243(13) .3740(4) -.0132(3) .0694(9) Uani d . 1 . . C
H10 .1689 .3994 -.0701 .083 Uiso calc R 1 . . H
C11 .22856(13) .2512(3) -.0285(3) .0632(8) Uani d . 1 . . C
H11 .2138 .1939 -.0975 .076 Uiso calc R 1 . . H
C12 .27716(12) .2101(3) .0581(2) .0546(7) Uani d . 1 . . C
H12 .2946 .1248 .0479 .066 Uiso calc R 1 . . H
C13 .57174(12) .3410(3) .8237(3) .0679(8) Uani d . 1 . . C
H13A .5790 .2455 .8432 .102 Uiso calc R 1 . . H
H13B .5637 .3880 .9018 .102 Uiso calc R 1 . . H
H13C .6061 .3807 .7926 .102 Uiso calc R 1 . . H
O1' 1.01898(9) .7563(2) .68323(15) .0689(6) Uani d . 1 . . O
N1' .89839(14) .6122(4) .3035(3) .1193(14) Uani d . 1 . . N
N2' 1.01957(9) .7867(2) .46670(17) .0479(5) Uani d . 1 . . N
H2' 1.0037 .7650 .3889 .058 Uiso calc R 1 . . H
C1' .99860(11) .7301(3) .5693(2) .0446(6) Uani d . 1 . . C
C2' .94784(10) .6320(3) .5402(2) .0455(6) Uani d . 1 . . C
C3' .92944(12) .5580(3) .6369(2) .0576(7) Uani d . 1 . . C
H3' .9508 .5691 .7197 .069 Uiso calc R 1 . . H
C4' .88133(13) .4649(3) .6277(3) .0581(7) Uani d . 1 . . C
C5' .84124(13) .3868(3) .6332(3) .0554(7) Uani d . 1 . . C
C6' .91935(13) .6196(3) .4093(3) .0668(8) Uani d . 1 . . C
C7' .79511(11) .2901(3) .6496(2) .0478(6) Uani d . 1 . . C
C8' .73735(12) .3048(3) .5861(3) .0588(7) Uani d . 1 . . C
H8' .7283 .3764 .5269 .071 Uiso calc R 1 . . H
C9' .69395(13) .2145(3) .6104(3) .0719(9) Uani d . 1 . . C
H9' .6554 .2252 .5684 .086 Uiso calc R 1 . . H
C10' .70703(14) .1083(3) .6964(3) .0733(9) Uani d . 1 . . C
H10' .6772 .0480 .7139 .088 Uiso calc R 1 . . H
C11' .76401(14) .0903(3) .7570(3) .0699(8) Uani d . 1 . . C
H11' .7730 .0158 .8129 .084 Uiso calc R 1 . . H
C12' .80749(12) .1811(3) .7356(3) .0570(7) Uani d . 1 . . C
H12' .8458 .1699 .7790 .068 Uiso calc R 1 . . H
C13' 1.06840(12) .8841(3) .4823(3) .0603(7) Uani d . 1 . . C
H13D 1.0622 .9495 .5493 .091 Uiso calc R 1 . . H
H13E 1.0702 .9314 .4009 .091 Uiso calc R 1 . . H
H13F 1.1051 .8360 .5072 .091 Uiso calc R 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 .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'
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 N2 C13 121.8(2) no
O1 C1 N2 125.1(2) no
O1 C1 C2 120.4(2) no
N2 C1 C2 114.5(2) no
C3 C2 C6 118.9(2) no
C3 C2 C1 120.7(2) no
C6 C2 C1 120.4(2) no
C2 C3 C4 122.7(3) no
C5 C4 C3 176.4(3) no
C4 C5 C7 176.1(3) no
N1 C6 C2 179.1(3) no
C8 C7 C12 118.9(2) no
C8 C7 C5 119.4(2) no
C12 C7 C5 121.7(2) no
C7 C8 C9 120.3(3) no
C10 C9 C8 120.0(3) no
C11 C10 C9 120.4(3) no
C10 C11 C12 120.4(3) no
C11 C12 C7 120.0(3) no
C1' N2' C13' 121.8(2) no
O1' C1' N2' 122.7(2) no
O1' C1' C2' 120.7(2) no
N2' C1' C2' 116.7(2) no
C3' C2' C6' 120.7(2) no
C3' C2' C1' 120.0(2) no
C6' C2' C1' 119.3(2) no
C2' C3' C4' 127.5(2) no
C5' C4' C3' 173.5(3) no
C4' C5' C7' 175.7(3) no
N1' C6' C2' 177.4(3) no
C12' C7' C8' 118.6(3) no
C12' C7' C5' 119.1(2) no
C8' C7' C5' 122.2(2) no
C9' C8' C7' 120.2(3) no
C8' C9' C10' 120.2(3) no
C9' C10' C11' 120.3(3) no
C12' C11' C10' 120.1(3) no
C11' C12' C7' 120.5(3) no
C1 N2 H2 119.1 no
C13 N2 H2 119.1 no
C2 C3 H3 118.6 no
C4 C3 H3 118.6 no
C7 C8 H8 119.8 no
C9 C8 H8 119.8 no
C10 C9 H9 120.0 no
C8 C9 H9 120.0 no
C11 C10 H10 119.8 no
C9 C10 H10 119.8 no
C10 C11 H11 119.8 no
C12 C11 H11 119.8 no
C11 C12 H12 120.0 no
C7 C12 H12 120.0 no
N2 C13 H13A 109.5 no
N2 C13 H13B 109.5 no
N2 C13 H13C 109.5 no
H13A C13 H13B 109.5 no
H13A C13 H13C 109.5 no
H13B C13 H13C 109.5 no
C1' N2' H2' 119.1 no
C13' N2' H2' 119.1 no
C2' C3' H3' 116.3 no
C4' C3' H3' 116.3 no
C9' C8' H8' 119.9 no
C7' C8' H8' 119.9 no
C8' C9' H9' 119.9 no
C10' C9' H9' 119.9 no
C9' C10' H10' 119.8 no
C11' C10' H10' 119.8 no
C12' C11' H11' 119.9 no
C10' C11' H11' 119.9 no
C11' C12' H12' 119.7 no
C7' C12' H12' 119.7 no
N2' C13' H13D 109.5 no
N2' C13' H13E 109.5 no
N2' C13' H13F 109.5 no
H13D C13' H13E 109.5 no
H13D C13' H13F 109.5 no
H13E C13' H13F 109.5 no
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 C1 . 1.213(3) yes
N1 C6 . 1.138(4) yes
N2 C1 . 1.332(3) yes
N2 C13 . 1.466(3) yes
C1 C2 . 1.513(3) yes
C2 C3 . 1.346(4) yes
C2 C6 . 1.423(4) yes
C3 C4 . 1.414(4) yes
C4 C5 . 1.199(3) yes
C5 C7 . 1.424(4) yes
C7 C8 . 1.378(4) no
C7 C12 . 1.391(3) no
C8 C9 . 1.381(4) no
C9 C10 . 1.375(4) no
C10 C11 . 1.351(4) no
C11 C12 . 1.383(4) no
O1' C1' . 1.228(3) yes
N1' C6' . 1.131(3) yes
N2' C1' . 1.329(3) yes
N2' C13' . 1.450(3) yes
C1' C2' . 1.495(3) yes
C2' C3' . 1.335(3) yes
C2' C6' . 1.420(3) yes
C3' C4' . 1.411(4) yes
C4' C5' . 1.191(4) yes
C5' C7' . 1.432(4) yes
C7' C12' . 1.385(4) no
C7' C8' . 1.393(4) no
C8' C9' . 1.365(4) no
C9' C10' . 1.366(4) no
C10' C11' . 1.371(4) no
C11' C12' . 1.362(4) no
N2 H2 . .8600 no
C3 H3 . .9300 no
C8 H8 . .9300 no
C9 H9 . .9300 no
C10 H10 . .9300 no
C11 H11 . .9300 no
C12 H12 . .9300 no
C13 H13A . .9600 no
C13 H13B . .9600 no
C13 H13C . .9600 no
N2' H2' . .8600 no
C3' H3' . .9300 no
C8' H8' . .9300 no
C9' H9' . .9300 no
C10' H10' . .9300 no
C11' H11' . .9300 no
C12' H12' . .9300 no
C13' H13D . .9600 no
C13' H13E . .9600 no
C13' H13F . .9600 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
C6 H2 2.38 yes
O1' H3' 2.45 yes
C6' H2' 2.41 yes
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
N2 H2 O1 2_656 .86 2.46 3.163(4) 139.3 yes
N2' H2' O1' 4_575 .86 2.19 2.939(3) 145.1 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
_geom_torsion_publ_flag
C13 N2 C1 O1 5.3(4) no
C13 N2 C1 C2 -174.0(2) no
O1 C1 C2 C3 -5.8(4) no
N2 C1 C2 C3 173.5(2) no
O1 C1 C2 C6 176.5(3) no
N2 C1 C2 C6 -4.2(3) no
C6 C2 C3 C4 -.4(4) no
C1 C2 C3 C4 -178.2(2) no
C12 C7 C8 C9 1.6(4) no
C5 C7 C8 C9 -176.3(3) no
C7 C8 C9 C10 -.5(5) no
C8 C9 C10 C11 -1.4(5) no
C9 C10 C11 C12 2.2(5) no
C10 C11 C12 C7 -1.0(4) no
C8 C7 C12 C11 -.9(4) no
C5 C7 C12 C11 176.9(2) no
C13' N2' C1' O1' .1(4) no
C13' N2' C1' C2' 179.6(2) no
O1' C1' C2' C3' -9.1(4) no
N2' C1' C2' C3' 171.5(2) no
O1' C1' C2' C6' 170.4(3) no
N2' C1' C2' C6' -9.1(4) no
C6' C2' C3' C4' -1.8(5) no
C1' C2' C3' C4' 177.7(3) no
C12' C7' C8' C9' 1.1(4) no
C5' C7' C8' C9' -176.2(3) no
C7' C8' C9' C10' -.6(5) no
C8' C9' C10' C11' -1.2(5) no
C9' C10' C11' C12' 2.4(5) no
C10' C11' C12' C7' -1.9(4) no
C8' C7' C12' C11' .2(4) no
C5' C7' C12' C11' 177.5(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21182078
