#------------------------------------------------------------------------------
#$Date: 2022-12-07 12:12:32 +0200 (Wed, 07 Dec 2022) $
#$Revision: 279777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/63/8106362.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_8106362
loop_
_publ_author_name
'Gao, Liang-Liang'
'Zhao, Xiao-Lei'
'Wu, Wei-Na'
_publ_section_title
;
 Crystal structure of 5-methylpyrazine-2-carbohydrazide, C6H8N4O
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              959
_journal_page_last               960
_journal_paper_doi               10.1515/ncrs-2018-0187
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C6 H8 N4 O'
_chemical_formula_weight         152.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 98.474(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.019(5)
_cell_length_b                   9.990(6)
_cell_length_c                   9.050(6)
_cell_measurement_reflns_used    488
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.15
_cell_measurement_theta_min      2.12
_cell_volume                     717.1(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3475
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.568
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1264
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0653P)²+0.1728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1058
_reflns_number_total             1264
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0187_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        717.1(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106362
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.53440(16) 0.28260(12) 0.19381(13) 0.0557(4) Uani 1 1 d . . . . .
N1 N 0.28756(17) 0.01491(13) 0.02094(15) 0.0423(4) Uani 1 1 d . . . . .
N2 N 0.12418(18) 0.22765(14) -0.14170(16) 0.0483(4) Uani 1 1 d . . . . .
N3 N 0.51085(17) 0.07141(14) 0.27442(15) 0.0436(4) Uani 1 1 d . . . . .
H3 H 0.456811 -0.003076 0.262270 0.052 Uiso 1 1 calc R U . . .
N4 N 0.6435(2) 0.08473(17) 0.39527(18) 0.0548(5) Uani 1 1 d D . . . .
H4A H 0.600(3) 0.120(2) 0.4685(19) 0.074(7) Uiso 1 1 d D . . . .
H4B H 0.706(3) 0.148(2) 0.367(3) 0.104(10) Uiso 1 1 d D . . . .
C1 C 0.1653(2) -0.00347(17) -0.09352(18) 0.0443(4) Uani 1 1 d . . . . .
H1 H 0.132935 -0.090753 -0.119462 0.053 Uiso 1 1 calc R U . . .
C2 C 0.0829(2) 0.10085(17) -0.17678(18) 0.0406(4) Uani 1 1 d . . . . .
C3 C 0.2481(2) 0.24671(17) -0.02734(18) 0.0444(4) Uani 1 1 d . . . . .
H3A H 0.280247 0.333889 -0.000652 0.053 Uiso 1 1 calc R U . . .
C4 C 0.3302(2) 0.14228(15) 0.05256(17) 0.0370(4) Uani 1 1 d . . . . .
C5 C 0.4676(2) 0.17114(15) 0.17919(17) 0.0383(4) Uani 1 1 d . . . . .
C6 C -0.0542(2) 0.07644(19) -0.3054(2) 0.0543(5) Uani 1 1 d . . . . .
H6A H -0.071441 -0.018139 -0.318802 0.081 Uiso 1 1 calc R U . . .
H6B H -0.156734 0.117503 -0.285243 0.081 Uiso 1 1 calc R U . . .
H6C H -0.022335 0.114331 -0.394668 0.081 Uiso 1 1 calc R U . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C4 115.71(14) . .
C2 N2 C3 116.64(14) . .
C5 N3 N4 121.66(15) . .
C5 N3 H3 119.2 . .
N4 N3 H3 119.2 . .
N3 N4 H4A 106.7(16) . .
N3 N4 H4B 104(2) . .
H4A N4 H4B 104(2) . .
N1 C1 C2 123.64(16) . .
N1 C1 H1 118.2 . .
C2 C1 H1 118.2 . .
N2 C2 C1 119.97(15) . .
N2 C2 C6 117.81(15) . .
C1 C2 C6 122.22(15) . .
N2 C3 C4 122.68(16) . .
N2 C3 H3A 118.7 . .
C4 C3 H3A 118.7 . .
N1 C4 C3 121.34(15) . .
N1 C4 C5 118.91(14) . .
C3 C4 C5 119.75(14) . .
O1 C5 N3 122.63(15) . .
O1 C5 C4 120.99(14) . .
N3 C5 C4 116.37(14) . .
C2 C6 H6A 109.5 . .
C2 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C2 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C5 1.234(2) .
N1 C1 1.330(2) .
N1 C4 1.338(2) .
N2 C2 1.336(2) .
N2 C3 1.339(2) .
N3 C5 1.329(2) .
N3 N4 1.415(2) .
N3 H3 0.8600 .
N4 H4A 0.866(9) .
N4 H4B 0.868(10) .
C1 C2 1.394(2) .
C1 H1 0.9300 .
C2 C6 1.499(2) .
C3 C4 1.380(2) .
C3 H3A 0.9300 .
C4 C5 1.496(2) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3 O1 0.86 2.18 2.927(3) 145.6 2_645 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C4 N1 C1 C2 -0.6(2) . . . .
C3 N2 C2 C1 1.4(2) . . . .
C3 N2 C2 C6 -179.36(14) . . . .
N1 C1 C2 N2 -0.9(3) . . . .
N1 C1 C2 C6 179.86(15) . . . .
C2 N2 C3 C4 -0.4(3) . . . .
C1 N1 C4 C3 1.6(2) . . . .
C1 N1 C4 C5 -179.57(13) . . . .
N2 C3 C4 N1 -1.1(3) . . . .
N2 C3 C4 C5 -179.97(14) . . . .
N4 N3 C5 O1 -3.4(3) . . . .
N4 N3 C5 C4 177.49(14) . . . .
N1 C4 C5 O1 165.20(15) . . . .
C3 C4 C5 O1 -15.9(2) . . . .
N1 C4 C5 N3 -15.7(2) . . . .
C3 C4 C5 N3 163.16(15) . . . .
