#------------------------------------------------------------------------------
#$Date: 2023-06-16 11:38:56 +0300 (Fri, 16 Jun 2023) $
#$Revision: 284494 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/73/8107388.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_8107388
loop_
_publ_author_name
'Zhong, Qi-Di'
'Wang, Rui'
'Zhao, Kai-Hui'
'Fu, Yu-Wei'
'Li, Dong-Mei'
_publ_section_title
;
 Crystal structure of 1,1′-(pyrazine-1,4-diyl)-bis(propan-2-one),
 C10H14N2O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              181
_journal_page_last               182
_journal_paper_doi               10.1515/ncrs-2022-0555
_journal_volume                  238
_journal_year                    2023
_chemical_formula_sum            'C10 H14 N2 O2'
_chemical_formula_weight         194.23
_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   geom
_cell_angle_alpha                90
_cell_angle_beta                 100.411(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.1183(15)
_cell_length_b                   9.787(4)
_cell_length_c                   12.649(5)
_cell_measurement_reflns_used    921
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.65
_cell_volume                     501.4(3)
_computing_cell_refinement       'APEX2-2008 [1]'
_computing_data_collection       'APEX2-2008 [1]'
_computing_data_reduction        'SAINT- 2008 [1]'
_computing_molecular_graphics    'SHELXTL [2]'
_computing_publication_material  'SHELXTL [2]'
_computing_structure_refinement  'SHELXL-2018/3 [2]'
_computing_structure_solution    'Bruker SHELXTL [2]'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2425
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         3.275
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     65
_refine_ls_number_reflns         873
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0484
_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)+(0.0100P)²+0.4100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0925
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                610
_reflns_number_total             873
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0555_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107388
_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   0.978
_shelx_estimated_absorpt_t_max   0.984
_exptl_absorpt_special_details   'SADABS; Bruker, 2008 [1]'
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
C1 C 0.9635(6) 0.8673(2) 0.52505(17) 0.0439(6) Uani 1 1 d . . . . .
H1 H 0.938009 0.775949 0.542018 0.053 Uiso 1 1 calc R U . . .
C2 C 0.9357(6) 1.1034(2) 0.56480(17) 0.0424(6) Uani 1 1 d . . . . .
H2 H 0.891603 1.174625 0.608791 0.051 Uiso 1 1 calc R U . . .
C3 C 0.7896(5) 0.9301(2) 0.69039(17) 0.0371(6) Uani 1 1 d . . . . .
C4 C 0.7133(6) 1.0419(2) 0.76291(17) 0.0406(6) Uani 1 1 d . . . . .
H4A H 0.531622 1.096201 0.725148 0.049 Uiso 1 1 calc R U . . .
H4B H 0.904139 1.101236 0.780532 0.049 Uiso 1 1 calc R U . . .
C5 C 0.6223(7) 0.9876(3) 0.86627(18) 0.0563(7) Uani 1 1 d . . . . .
H5A H 0.436503 0.927184 0.849271 0.085 Uiso 1 1 calc R U . . .
H5B H 0.566517 1.062471 0.908589 0.085 Uiso 1 1 calc R U . . .
H5C H 0.806578 0.938647 0.906227 0.085 Uiso 1 1 calc R U . . .
N1 N 0.8918(5) 0.96796(17) 0.59718(13) 0.0357(5) Uani 1 1 d . . . . .
O1 O 0.7626(4) 0.80931(16) 0.71106(13) 0.0555(5) Uani 1 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 '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
C2 C1 N1 123.02(19) 3_776 .
C2 C1 H1 118.5 3_776 .
N1 C1 H1 118.5 . .
C1 C2 N1 122.36(19) 3_776 .
C1 C2 H2 118.8 3_776 .
N1 C2 H2 118.8 . .
O1 C3 N1 120.0(2) . .
O1 C3 C4 122.65(19) . .
N1 C3 C4 117.37(18) . .
C3 C4 C5 112.50(19) . .
C3 C4 H4A 109.1 . .
C5 C4 H4A 109.1 . .
C3 C4 H4B 109.1 . .
C5 C4 H4B 109.1 . .
H4A C4 H4B 107.8 . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C3 N1 C2 125.39(17) . .
C3 N1 C1 120.00(17) . .
C2 N1 C1 114.62(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.310(3) 3_776
C1 N1 1.410(3) .
C1 H1 0.9300 .
C2 N1 1.409(3) .
C2 H2 0.9300 .
C3 O1 1.220(2) .
C3 N1 1.373(3) .
C3 C4 1.497(3) .
C4 C5 1.520(3) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
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
O1 C3 C4 C5 3.7(3) . . . .
N1 C3 C4 C5 -176.6(2) . . . .
O1 C3 N1 C2 -179.3(2) . . . .
C4 C3 N1 C2 1.0(3) . . . .
O1 C3 N1 C1 0.4(3) . . . .
C4 C3 N1 C1 -179.2(2) . . . .
C1 C2 N1 C3 179.5(2) 3_776 . . .
C1 C2 N1 C1 -0.3(4) 3_776 . . .
C2 C1 N1 C3 -179.5(2) 3_776 . . .
C2 C1 N1 C2 0.3(4) 3_776 . . .
