#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:18:17 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179659 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/12/4511295.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_4511295
loop_
_publ_author_name
'Jarzembska, Katarzyna N.'
'Hoser, Anna A.'
'Kamiński, Radosław'
'Madsen, Anders Ø.'
'Durka, Krzysztof'
'Woźniak, Krzysztof'
_publ_section_title
;
 Combined Experimental and Computational Studies of Pyrazinamide and
 Nicotinamide in the Context of Crystal Engineering and Thermodynamics
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3453
_journal_paper_doi               10.1021/cg500376z
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C5 H5 N3 O'
_chemical_formula_sum            'C5 H5 N3 O'
_chemical_formula_weight         123.11
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 101.0440(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.3396(7)
_cell_length_b                   3.6211(2)
_cell_length_c                   10.6131(5)
_cell_measurement_temperature    90
_cell_volume                     540.88(5)
_diffrn_ambient_temperature      90
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device
;
Bruker AXS Kappa APEX II Ultra diffractometer
;
_diffrn_measurement_device_type  'APEX II CCD detector'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_source         'TXS rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38036
_diffrn_reflns_theta_full        58.02
_diffrn_reflns_theta_max         58.025
_diffrn_reflns_theta_min         2.895
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.050
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Absorption correction done by SORTAV
 Blessing, R. H.: (1995) Acta Cryst. A51, 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.087
_refine_diff_density_max         +0.16
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     204
_refine_ls_number_reflns         6241
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0153
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
w=1/[σ²(Fo)]
;
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0237
_refine_ls_wR_factor_ref         0.0237
_reflns_number_gt                6241
_reflns_number_total             7618
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            cg500376z_si_002.cif
_cod_data_source_block           beta-pyra-90K
_cod_depositor_comments
'Adding full bibliography for 4511295--4511296.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4511295
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_type_symbol
_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_occupancy
_atom_site_calc_flag
O O1 0.60100(1) 0.41140(4) 0.13077(2) 0.01389(4) Uani 1 d
N N1 0.584134(1) 0.23433(4) -0.07824(1) 0.01355(4) Uani 1 d
N N2 0.87655(1) 0.02050(4) 0.21781(1) 0.01217(4) Uani 1 d
N N3 0.767141(1) -0.02307(3) -0.03027(1) 0.01048(3) Uani 1 d
C C1 0.632069(1) 0.26420(4) 0.04179(1) 0.01034(3) Uani 1 d
C C2 0.731903(1) 0.11481(3) 0.06744(1) 0.00919(3) Uani 1 d
C C3 0.78608(1) 0.13325(4) 0.19156(1) 0.01129(4) Uani 1 d
C C4 0.91218(1) -0.11376(4) 0.11952(1) 0.01152(4) Uani 1 d
C C5 0.85748(1) -0.13763(4) -0.00387(1) 0.01128(4) Uani 1 d
H H1A 0.6163(3) 0.124(2) -0.1462(4) 0.02832 Uani 1 d
H H1B 0.5187(2) 0.348(2) -0.0995(6) 0.02930 Uani 1 d
H H3 0.7560(4) 0.247(2) 0.2693(4) 0.02943 Uani 1 d
H H4 0.9857(1) -0.202(2) 0.1394(6) 0.02825 Uani 1 d
H H5 0.8863(4) -0.254(2) -0.0822(4) 0.02991 Uani 1 d
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 'Su & Coppens, Acta. Cryst. (1997) A53, 749'
H H 0.0000 0.0000 'Su & Coppens, Acta. Cryst. (1997) A53, 749'
N N 0.0060 0.0030 'Su & Coppens. Acta. Cryst. (1997) A53, 749'
O O 0.0106 0.0060 'Su & Coppens, Acta. Cryst. (1997) A53, 749'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 N1 124.69(2)
O1 C1 C2 119.01(1)
N1 C1 C2 116.28(1)
N2 C3 C2 121.60(2)
N2 C3 H3 118.0(3)
N2 C4 C5 121.65(2)
N2 C4 H4 117.3(4)
N3 C2 C1 118.84(1)
N3 C2 C3 121.72(1)
N3 C5 C4 121.69(1)
N3 C5 H5 117.2(3)
C1 N1 H1A 119.5(3)
C1 N1 H1B 117.9(3)
C1 C2 C3 119.42(1)
C2 N3 C5 116.67(1)
C2 C3 H3 120.4(3)
C3 N2 C4 116.65(1)
C4 C5 H5 121.1(3)
C5 C4 H4 121.1(4)
H1A N1 H1B 122.3(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2392(2)
N1 C1 1.3310(2)
N1 H1A 1.010(1)
N1 H1B 1.010(1)
N2 C3 1.3374(2)
N2 C4 1.3378(2)
N3 C2 1.3345(2)
N3 C5 1.3378(2)
C1 C2 1.5056(2)
C2 C3 1.3968(2)
C3 H3 1.083(1)
C4 C5 1.3943(2)
C4 H4 1.083(1)
C5 H5 1.083(1)
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
O1 C1 N1 H1A 176.3(2)
O1 C1 N1 H1B 2.6(3)
O1 C1 C2 N3 -175.95(2)
O1 C1 C2 C3 2.26(1)
N1 C1 C2 N3 2.47(1)
N1 C1 C2 C3 -179.33(1)
N2 C3 C2 N3 1.41(1)
N2 C3 C2 C1 -176.74(1)
N2 C4 C5 N3 0.88(1)
N2 C4 C5 H5 -178.1(1)
N3 C2 C3 H3 179.79(10)
N3 C5 C4 H4 -178.64(10)
C1 C2 N3 C5 177.16(1)
C1 C2 C3 H3 1.6(3)
C2 N3 C5 C4 -0.09(1)
C2 N3 C5 H5 178.92(9)
C2 C1 N1 H1A -2.0(3)
C2 C1 N1 H1B -175.7(1)
C2 C3 N2 C4 -0.59(1)
C3 N2 C4 C5 -0.50(1)
C3 N2 C4 H4 179.03(10)
C3 C2 N3 C5 -1.00(1)
C4 N2 C3 H3 -179.0(1)
H4 C4 C5 H5 2.4(4)
