#------------------------------------------------------------------------------
#$Date: 2014-07-11 17:35:18 +0300 (Fri, 11 Jul 2014) $
#$Revision: 120071 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/56/1505699.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1505699
loop_
_publ_author_name
'Grabowski, S\/lawomir J'
'Dubis, Alina T.'
'Palusiak, Marcin'
'Leszczynski, Jerzy'
_publ_section_title
;
 Heteronuclear intermolecular resonance-assisted hydrogen bonds. The
 structure of pyrrole-2-carboxamide (PyCa).
;
_journal_issue                   12
_journal_name_full               'The journal of physical chemistry. B'
_journal_page_first              5875
_journal_page_last               5882
_journal_volume                  110
_journal_year                    2006
_chemical_formula_moiety         'C5 H6 N2 O'
_chemical_formula_sum            'C5 H6 N2 O'
_chemical_formula_weight         110.12
_chemical_name_systematic
; 
1-H-pyrrole-2-carboxylic acid amide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_date             2005-05-23T15:23:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.545(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.138(4)
_cell_length_b                   5.0768(18)
_cell_length_c                   14.813(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(1)
_cell_measurement_theta_max      17.89
_cell_measurement_theta_min      9.30
_cell_volume                     1048.5(6)
_computing_cell_refinement
;
MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989a)
;
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989a)
;
_computing_data_reduction
;
TEXSAN (Molecular  Structure Corporation, 1989b)' 
;
_computing_molecular_graphics
;
PLATON (Spek, 1998)
;
_computing_publication_material
;
PLATON (Spek, 1998)
MERCURY 1.3(The Cambridge Crystallographic Data Centre, 2004)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(1)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'AFC5S Rigaku'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4031
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.79
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.143
_refine_ls_extinction_coef       0.0112(15)
_refine_ls_extinction_expression
;
 Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
;
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     86
_refine_ls_number_reflns         1213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0485P)^2^] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0777
_reflns_number_gt                683
_reflns_number_total             1213
_reflns_threshold_expression     >2sigma(I)
_[local]_cod_data_source_file    jp055334vsi20050920_061244.cif
_[local]_cod_data_source_block   adu_1
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_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               1505699
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
O21 O 0.12405(5) -0.14632(14) 0.03272(6) 0.0457(3) Uani 1 d .
N1 N 0.31432(7) -0.0081(2) 0.11004(7) 0.0440(3) Uani 1 d .
H1 H 0.3132(11) -0.152(3) 0.0754(11) 0.068(4) Uiso 1 d .
N21 N 0.07315(9) 0.2589(2) 0.06409(8) 0.0495(3) Uani 1 d .
H211 H 0.0915(10) 0.412(3) 0.0772(10) 0.061(4) Uiso 1 d .
H212 H 0.0138(11) 0.214(3) 0.0383(10) 0.053(4) Uiso 1 d .
C2 C 0.23701(8) 0.1503(2) 0.11268(7) 0.0337(3) Uani 1 d .
C21 C 0.14161(8) 0.0776(2) 0.06626(7) 0.0356(3) Uani 1 d .
C3 C 0.26839(9) 0.3616(2) 0.16802(8) 0.0422(3) Uani 1 d .
H3 H 0.2311 0.5014 0.1824 0.051 Uiso 1 calc R
C4 C 0.36653(9) 0.3275(2) 0.19859(8) 0.0484(3) Uani 1 d .
H4 H 0.4065 0.4398 0.2372 0.058 Uiso 1 calc R
C5 C 0.39284(9) 0.0990(3) 0.16125(9) 0.0504(3) Uani 1 d .
H5 H 0.4544 0.0287 0.1696 0.06 Uiso 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O21 0.0402(5) 0.0352(5) 0.0594(5) -0.0118(4) 0.0013(4) 0.0016(4)
N1 0.0397(6) 0.0422(6) 0.0486(6) -0.0130(4) 0.0031(5) 0.0050(5)
N21 0.0384(7) 0.0371(6) 0.0684(8) -0.0106(5) -0.0047(5) 0.0064(5)
C2 0.0370(6) 0.0307(5) 0.0335(5) 0.0000(5) 0.0067(4) 0.0031(5)
C21 0.0392(7) 0.0336(5) 0.0343(6) 0.0006(4) 0.0069(5) 0.0026(5)
C3 0.0493(8) 0.0346(6) 0.0430(6) -0.0042(5) 0.0082(5) 0.0017(5)
C4 0.0457(8) 0.0502(7) 0.0477(7) -0.0103(6) 0.0028(6) -0.0090(6)
C5 0.0337(7) 0.0629(9) 0.0528(8) -0.0092(6) 0.0023(6) 0.0022(6)
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_attenuator_code
_diffrn_attenuator_scale
1 1.000
2 2.653
3 7.112
4 18.159
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 0 4
1 1 -1
-1 -1 3
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 N1 C2 109.57(11)
C5 N1 H1 126.0(10)
C2 N1 H1 124.2(10)
C21 N21 H211 116.3(10)
C21 N21 H212 117.5(9)
H211 N21 H212 125.0(14)
N1 C2 C3 107.20(10)
N1 C2 C21 121.43(10)
C3 C2 C21 131.28(10)
O21 C21 N21 121.57(11)
O21 C21 C2 121.73(10)
N21 C21 C2 116.66(11)
C2 C3 C4 107.51(10)
C2 C3 H3 126.2
C4 C3 H3 126.2
C5 C4 C3 107.28(11)
C5 C4 H4 126.4
C3 C4 H4 126.4
N1 C5 C4 108.44(11)
N1 C5 H5 125.8
C4 C5 H5 125.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O21 C21 1.2490(13)
N1 C5 1.3505(15)
N1 C2 1.3626(15)
N1 H1 0.890(15)
N21 C21 1.3322(15)
N21 H211 0.835(16)
N21 H212 0.892(15)
C2 C3 1.3781(16)
C2 C21 1.4562(16)
C3 C4 1.3971(18)
C3 H3 0.93
C4 C5 1.3631(18)
C4 H4 0.93
C5 H5 0.93
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 C3 -0.53(13)
C5 N1 C2 C21 -177.54(10)
N1 C2 C21 O21 9.75(16)
C3 C2 C21 O21 -166.45(12)
N1 C2 C21 N21 -172.49(11)
C3 C2 C21 N21 11.31(18)
N1 C2 C3 C4 0.14(13)
C21 C2 C3 C4 176.74(10)
C2 C3 C4 C5 0.29(14)
C2 N1 C5 C4 0.72(15)
C3 C4 C5 N1 -0.62(15)
_journal_paper_doi 10.1021/jp055334v