#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/43/2004301.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_2004301
loop_
_publ_author_name
'Cativiela, C.'
'Díaz-de-Villegas, M. D.'
'Gálvez, J. A.'
'López, M. P.'
_publ_section_title
;
 trans-1-Cyano-2-phenylcyclopropanecarboxamide
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2703
_journal_page_last               2705
_journal_paper_doi               10.1107/S010827019500936X
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C11 H10 N2 O'
_chemical_formula_weight         186.21
_chemical_name_systematic
;
Trans-1-cyano-2-phenylcyclopropanecarboxamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 91.59(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.292(2)
_cell_length_b                   10.139(2)
_cell_length_c                   10.095(2)
_cell_measurement_reflns_used    39
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      4.5
_cell_volume                     950.7(3)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1993)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1989)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2206
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         2.85
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       Prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.071
_refine_ls_goodness_of_fit_obs   1.109
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_restrained_S_obs      1.109
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_obs          0.0435
_refine_ls_shift/esd_max         0.028
_refine_ls_shift/esd_mean        0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.0525P)^2^ + 0.1576P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.1171
_refine_ls_wR_factor_obs         0.1005
_reflns_number_observed          1170
_reflns_number_total             1649
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            na1194.cif
_cod_data_source_block           pili93
_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/n'
_cod_original_formula_sum        'C11 H10 N2 O1'
_cod_database_code               2004301
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_occupancy
_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_type_symbol
O1 1 0.08289(15) 0.9678(2) 0.34256(14) 0.0639(5) Uani d . O
N1 1 0.1893(2) 0.9559(2) 0.5446(2) 0.0495(5) Uani d . N
H 1 0.1072(2) 0.9825(2) 0.5841(2) 0.064(2) Uiso d R H
H' 1 0.2688(2) 0.9382(2) 0.5949(2) 0.064(2) Uiso d R H
N2 1 0.5307(2) 0.8237(2) 0.5133(2) 0.0549(5) Uani d . N
C1 1 0.3220(2) 0.8897(2) 0.3525(2) 0.0371(5) Uani d . C
C2 1 0.3607(2) 0.9479(2) 0.2154(2) 0.0398(5) Uani d . C
H2 1 0.2914(2) 1.0205(2) 0.1797(2) 0.064(2) Uiso d R H
C3 1 0.3032(2) 0.8125(2) 0.2227(2) 0.0499(6) Uani d . C
H3A 1 0.1977(2) 0.8019(2) 0.2001(2) 0.064(2) Uiso d R H
H3B 1 0.3734(2) 0.7268(2) 0.2201(2) 0.064(2) Uiso d R H
C4 1 0.1881(2) 0.9414(2) 0.4142(2) 0.0391(5) Uani d . C
C5 1 0.4395(2) 0.8525(2) 0.4406(2) 0.0377(5) Uani d . C
C6 1 0.5129(2) 0.9792(2) 0.1828(2) 0.0365(5) Uani d . C
C7 1 0.5492(2) 1.1093(2) 0.1553(2) 0.0445(5) Uani d . C
H7 1 0.4635(2) 1.1772(2) 0.1604(2) 0.064(2) Uiso d R H
C8 1 0.6874(2) 1.1418(2) 0.1199(2) 0.0520(6) Uani d . C
H8 1 0.7151(2) 1.2328(2) 0.1003(2) 0.064(2) Uiso d R H
C9 1 0.7917(2) 1.0460(3) 0.1125(2) 0.0540(6) Uani d . C
H9 1 0.8951(2) 1.0739(3) 0.0997(2) 0.064(2) Uiso d R H
C10 1 0.7580(2) 0.9177(3) 0.1406(2) 0.0525(6) Uani d . C
H10 1 0.8296(2) 0.8418(3) 0.1399(2) 0.064(2) Uiso d R H
C11 1 0.6188(2) 0.8835(2) 0.1745(2) 0.0459(5) Uani d . C
H11 1 0.5926(2) 0.7868(2) 0.1996(2) 0.064(2) Uiso d R H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C4 N1 H 118.91(11) ?
C4 N1 H' 121.49(11) ?
H N1 H' 119.6 ?
C5 C1 C4 117.3(2) yes
C5 C1 C3 117.4(2) ?
C4 C1 C3 117.2(2) yes
C5 C1 C2 117.3(2) yes
C4 C1 C2 116.8(2) yes
C3 C1 C2 57.09(13) yes
C3 C2 C6 123.7(2) ?
C3 C2 C1 60.65(13) yes
C6 C2 C1 121.3(2) yes
C3 C2 H2 117.14(12) ?
C6 C2 H2 110.76(11) ?
C1 C2 H2 114.99(10) ?
C2 C3 C1 62.26(13) yes
C2 C3 H3A 116.12(12) ?
C1 C3 H3A 109.61(11) ?
C2 C3 H3B 121.61(12) ?
C1 C3 H3B 112.03(12) ?
H3A C3 H3B 119.3 ?
O1 C4 N1 123.1(2) yes
O1 C4 C1 119.1(2) yes
N1 C4 C1 117.8(2) yes
N2 C5 C1 178.3(2) yes
C11 C6 C7 118.4(2) ?
C11 C6 C2 122.8(2) ?
C7 C6 C2 118.7(2) ?
C8 C7 C6 120.6(2) ?
C8 C7 H7 124.41(14) ?
C6 C7 H7 114.97(12) ?
C9 C8 C7 120.5(2) ?
C9 C8 H8 117.67(14) ?
C7 C8 H8 121.84(14) ?
C10 C9 C8 119.6(2) ?
C10 C9 H9 120.96(13) ?
C8 C9 H9 118.84(14) ?
C9 C10 C11 120.5(2) ?
C9 C10 H10 124.27(13) ?
C11 C10 H10 115.24(14) ?
C6 C11 C10 120.5(2) ?
C6 C11 H11 118.19(12) ?
C10 C11 H11 121.25(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 1.229(2) yes
N1 C4 1.324(2) yes
N1 H 0.91 ?
N1 H' 0.90 ?
N2 C5 1.143(2) yes
C1 C5 1.440(3) yes
C1 C4 1.502(3) yes
C1 C3 1.531(3) yes
C1 C2 1.555(3) yes
C2 C3 1.475(3) yes
C2 C6 1.495(3) yes
C2 H2 1.04 ?
C3 H3A 1.01 ?
C3 H3B 1.09 ?
C6 C11 1.386(3) ?
C6 C7 1.392(3) ?
C7 C8 1.382(3) ?
C7 H7 1.05 ?
C8 C9 1.376(3) ?
C8 H8 0.98 ?
C9 C10 1.370(3) ?
C9 H9 1.01 ?
C10 C11 1.391(3) ?
C10 H10 1.02 ?
C11 H11 1.04 ?
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 C1 C2 C3 106.5(2) ?
C4 C1 C2 C3 -106.5(2) ?
C3 C1 C2 C3 0.0 ?
C5 C1 C2 C6 -7.3(3) yes
C4 C1 C2 C6 139.8(2) ?
C3 C1 C2 C6 -113.7(2) ?
C6 C2 C3 C1 110.0(2) ?
C1 C2 C3 C1 0.0 ?
C5 C1 C3 C2 -106.3(2) ?
C4 C1 C3 C2 105.8(2) ?
C2 C1 C3 C2 0.0 ?
C5 C1 C4 O1 -176.3(2) ?
C3 C1 C4 O1 -28.3(3) yes
C2 C1 C4 O1 36.6(3) yes
C5 C1 C4 N1 3.4(3) ?
C3 C1 C4 N1 151.4(2) ?
C2 C1 C4 N1 -143.7(2) ?
C4 C1 C5 N2 1.(7) ?
C3 C1 C5 N2 -148.(7) ?
C2 C1 C5 N2 147.(7) ?
C3 C2 C6 C11 -9.2(3) yes
C1 C2 C6 C11 64.3(3) ?
C3 C2 C6 C7 168.6(2) ?
C1 C2 C6 C7 -117.9(2) ?
C11 C6 C7 C8 0.3(3) ?
C2 C6 C7 C8 -177.6(2) ?
C6 C7 C8 C9 -0.6(3) ?
C7 C8 C9 C10 -0.1(3) ?
C8 C9 C10 C11 1.0(3) ?
C7 C6 C11 C10 0.6(3) ?
C2 C6 C11 C10 178.5(2) ?
C9 C10 C11 C6 -1.3(3) ?
