##############################################################################
### ###
### Electronic paper (Acta Crystallographica Section E) ###
### ###
##############################################################################
# #
# This CIF contains the data in a paper accepted for publication in Acta #
# Crystallographica Section E. It conforms to the requirements of Notes #
# for Authors for Section E, and has been peer reviewed under the auspices #
# of the IUCr Commission on Journals. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary is obtainable from #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1. #
# #
# Software is freely available for graphical display of the structure(s) in #
# this CIF. For information consult the CIF home page http://www.iucr.org/ #
# cif/home.html #
# #
##############################################################################
data_global
_audit_creation_method 'SHELXL97 and manual editing'
_journal_date_recd_electronic 2007-10-25
_journal_date_accepted 2007-12-11
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2008
_journal_volume 64
_journal_issue 1
_journal_page_first o302
_journal_page_last o303
_journal_paper_category QO
_journal_coeditor_code BH2145
_publ_contact_author_name 'Adailton J. Bortoluzzi'
_publ_contact_author_address
;
Depto. de Qu\'imica - Universidade Federal de Santa Catarina
88040-900 - Florian\'opolis, Santa Catarina
Brazil
;
_publ_contact_author_email adajb@qmc.ufsc.br
_publ_contact_author_fax '55(48)37216888'
_publ_contact_author_phone '55(48)37216844'
_publ_section_title
;
Nicotinohydrazide
;
loop_
_publ_author_name
_publ_author_address
"Priebe, Jacks P."
;
Depto. de Qu\'imica
Universidade Federal de Santa Catarina
88040-900 Florian\'opolis, Santa Catarina
Brazil
;
"Mello, Renata S."
;
Depto. de Qu\'imica
Universidade Federal de Santa Catarina
88040-900 Florian\'opolis, Santa Catarina
Brazil
;
"Nome, Faruk"
;
Depto. de Qu\'imica
Universidade Federal de Santa Catarina
88040-900 Florian\'opolis, Santa Catarina
Brazil
;
"Bortoluzzi, Adailton J."
;
Depto. de Qu\'imica
Universidade Federal de Santa Catarina
88040-900 Florian\'opolis, Santa Catarina
Brazil
;
data_I
_audit_creation_method SHELXL97
_chemical_name_systematic
;
Pyridine-3-carbohydrazide
;
_chemical_name_common
;
Nicotinohydrazide
;
_chemical_formula_moiety 'C6 H7 N3 O'
_chemical_formula_sum 'C6 H7 N3 O'
_chemical_formula_iupac 'C6 H7 N3 O'
_chemical_formula_weight 137.15
_chemical_melting_point ?
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'
_symmetry_space_group_name_Hall 'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
_cell_length_a 3.8855(7)
_cell_length_b 10.5191(5)
_cell_length_c 15.9058(9)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 650.10(13)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 25
_cell_measurement_theta_min 5.5
_cell_measurement_theta_max 18.7
_cell_measurement_temperature 293(2)
_exptl_crystal_description prismatic
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.46
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.20
_exptl_crystal_density_diffrn 1.401
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 288
_exptl_absorpt_coefficient_mu 0.101
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_special_details ?
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Enraf--Nonius CAD-4'
_diffrn_measurement_method \w--2\q
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 1534
_diffrn_reflns_av_R_equivalents 0.015
_diffrn_reflns_av_sigmaI/netI 0.022
_diffrn_reflns_theta_min 2.32
_diffrn_reflns_theta_max 28.95
_diffrn_reflns_theta_full 28.9
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min -5
_diffrn_reflns_limit_h_max 2
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 0
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_limit_l_max 0
_diffrn_standards_number 3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% '<1'
_reflns_number_total 1051
_reflns_number_gt 866
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.049
_refine_ls_R_factor_gt 0.031
_refine_ls_wR_factor_gt 0.078
_refine_ls_wR_factor_ref 0.087
_refine_ls_goodness_of_fit_ref 1.09
_refine_ls_restrained_S_all 1.09
_refine_ls_number_reflns 1051
_refine_ls_number_parameters 92
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0344P)^2^+0.1144P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.176
_refine_diff_density_min -0.148
_refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)'
_refine_ls_extinction_coef 0.040(6)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack ?
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 0.0000
'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 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_cell_refinement 'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction 'HELENA (Spek, 1996)'
_computing_structure_solution 'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
PLATON (Spek, 2003) and Mercury (Macrae et al., 2006)
;
_computing_publication_material 'SHELXL97 (Sheldrick, 1997)'
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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3825(5) 0.84759(16) 0.25136(11) 0.0373(4) Uani d . 1 . .
H H1 0.4007 0.9092 0.2930 0.045 Uiso calc R 1 . .
C C2 0.2298(5) 0.73203(14) 0.27215(10) 0.0319(4) Uani d . 1 . .
C C3 0.2025(5) 0.64013(16) 0.20969(10) 0.0382(4) Uani d . 1 . .
H H3 0.1029 0.5617 0.2212 0.046 Uiso calc R 1 . .
C C4 0.3262(6) 0.66735(19) 0.12995(11) 0.0455(5) Uani d . 1 . .
H H4 0.3114 0.6076 0.0870 0.055 Uiso calc R 1 . .
C C5 0.4720(7) 0.78517(19) 0.11576(11) 0.0472(5) Uani d . 1 . .
H H5 0.5524 0.8032 0.0620 0.057 Uiso calc R 1 . .
C C6 0.0965(5) 0.71648(17) 0.36028(10) 0.0344(4) Uani d . 1 . .
N N1 0.5043(5) 0.87491(14) 0.17489(10) 0.0440(4) Uani d . 1 . .
N N2 0.1167(5) 0.59906(15) 0.39179(9) 0.0405(4) Uani d . 1 . .
H H2N 0.2155 0.5365 0.3637 0.049 Uiso d R 1 . .
N N3 -0.0001(5) 0.56759(16) 0.47365(9) 0.0472(4) Uani d . 1 . .
H H3NA 0.0877 0.6189 0.5112 0.057 Uiso d R 1 . .
H H3NB -0.2101 0.5876 0.4784 0.057 Uiso d R 1 . .
O O1 -0.0227(5) 0.80795(12) 0.39876(8) 0.0487(4) Uani d . 1 . .
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
C1 0.0405(9) 0.0307(7) 0.0405(9) 0.0021(8) -0.0023(8) -0.0007(6)
C2 0.0312(8) 0.0314(7) 0.0330(7) 0.0041(8) -0.0025(7) -0.0001(6)
C3 0.0445(11) 0.0316(8) 0.0384(8) 0.0007(8) -0.0049(8) -0.0009(7)
C4 0.0594(14) 0.0442(9) 0.0328(8) 0.0060(11) -0.0039(9) -0.0057(7)
C5 0.0550(13) 0.0522(10) 0.0345(8) 0.0062(11) 0.0050(9) 0.0069(8)
C6 0.0324(9) 0.0367(8) 0.0339(7) 0.0012(8) -0.0035(7) -0.0040(7)
N1 0.0481(10) 0.0388(7) 0.0451(8) 0.0002(8) 0.0019(8) 0.0078(6)
N2 0.0505(10) 0.0373(7) 0.0337(7) 0.0027(7) 0.0057(7) 0.0007(6)
N3 0.0557(11) 0.0519(9) 0.0338(7) -0.0021(10) 0.0028(8) 0.0045(6)
O1 0.0604(10) 0.0447(7) 0.0409(6) 0.0120(7) 0.0060(7) -0.0060(5)
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
C1 N1 . 1.336(2) ?
C1 C2 . 1.392(2) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.390(2) ?
C2 C6 . 1.503(2) ?
C3 C4 . 1.386(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.381(3) ?
C4 H4 . 0.9300 ?
C5 N1 . 1.338(2) ?
C5 H5 . 0.9300 ?
C6 O1 . 1.231(2) ?
C6 N2 . 1.335(2) ?
N2 N3 . 1.418(2) ?
N2 H2N . 0.8830 ?
N3 H3NA . 0.8746 ?
N3 H3NB . 0.8461 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 123.70(16) ?
N1 C1 H1 . . 118.2 ?
C2 C1 H1 . . 118.2 ?
C3 C2 C1 . . 118.02(16) ?
C3 C2 C6 . . 124.35(16) ?
C1 C2 C6 . . 117.60(15) ?
C4 C3 C2 . . 118.93(17) ?
C4 C3 H3 . . 120.5 ?
C2 C3 H3 . . 120.5 ?
C5 C4 C3 . . 118.49(17) ?
C5 C4 H4 . . 120.8 ?
C3 C4 H4 . . 120.8 ?
N1 C5 C4 . . 123.81(17) ?
N1 C5 H5 . . 118.1 ?
C4 C5 H5 . . 118.1 ?
O1 C6 N2 . . 123.96(16) ?
O1 C6 C2 . . 120.55(16) ?
N2 C6 C2 . . 115.49(15) ?
C1 N1 C5 . . 117.04(16) ?
C6 N2 N3 . . 122.80(15) ?
C6 N2 H2N . . 121.7 ?
N3 N2 H2N . . 115.4 ?
N2 N3 H3NA . . 111.0 ?
N2 N3 H3NB . . 109.4 ?
H3NA N3 H3NB . . 99.3 ?
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 H2N N1 4_645 0.88 2.11 2.975(2) 166.4 y
N3 H3NA O1 3_566 0.87 2.22 3.045(2) 157.0 y
N3 H3NB O1 3_466 0.85 2.55 3.155(2) 129.5 y