#------------------------------------------------------------------------------
#$Date: 2019-11-24 08:48:42 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237364 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/45/1554576.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_1554576
loop_
_publ_author_name
'Cao, Yuan'
'Liu, Jie'
'Liu, Fanmin'
'Jiang, Lvqi'
'Yi, Wenbin'
_publ_section_title
;
 Copper-catalyzed direct and odorless selenylation with a sodium
 selenite-based reagent
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              825
_journal_paper_doi               10.1039/C8QO01355A
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C10 H8 N2 Se'
_chemical_formula_weight         235.14
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-07-25 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.268(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.150(5)
_cell_length_b                   11.643(7)
_cell_length_c                   12.098(8)
_cell_measurement_reflns_used    1382
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.31
_cell_measurement_theta_min      2.43
_cell_volume                     1002.9(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0299
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5477
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.433
_exptl_absorpt_coefficient_mu    3.697
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0388
_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)+(0.0396P)²+0.6535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.1044
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1168
_reflns_number_total             1761
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qo01355a2.cif
_cod_data_source_block           20170331lmf_0m_a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1554576
_shelx_shelxl_version_number     2014/7
_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   0.435
_shelx_estimated_absorpt_t_max   0.497
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
C1 C 0.8165(9) 0.8979(5) 0.4488(5) 0.124(2) Uani 1 1 d . .
H1A H 0.8910 0.9038 0.5188 0.186 Uiso 1 1 calc R U
H1B H 0.7927 0.9734 0.4187 0.186 Uiso 1 1 calc R U
H1C H 0.8829 0.8534 0.3983 0.186 Uiso 1 1 calc R U
C2 C 0.6728(5) 0.6764(3) 0.5096(3) 0.0587(10) Uani 1 1 d . .
C3 C 0.7059(5) 0.5827(3) 0.4364(3) 0.0511(9) Uani 1 1 d . .
C4 C 0.6912(6) 0.5687(4) 0.3215(3) 0.0677(11) Uani 1 1 d . .
H4 H 0.6552 0.6299 0.2749 0.081 Uiso 1 1 calc R U
C5 C 0.7306(6) 0.4631(4) 0.2779(3) 0.0717(11) Uani 1 1 d . .
H5 H 0.7211 0.4528 0.2014 0.086 Uiso 1 1 calc R U
C6 C 0.7854(5) 0.3705(3) 0.3487(3) 0.0614(10) Uani 1 1 d . .
C7 C 0.8015(5) 0.3823(3) 0.4628(3) 0.0546(9) Uani 1 1 d . .
H7 H 0.8381 0.3211 0.5092 0.066 Uiso 1 1 calc R U
C8 C 0.7610(4) 0.4886(3) 0.5051(3) 0.0467(8) Uani 1 1 d . .
C9 C 0.7086(5) 0.6358(3) 0.6147(4) 0.0618(10) Uani 1 1 d . .
H9 H 0.6980 0.6787 0.6787 0.074 Uiso 1 1 calc R U
C10 C 0.8218(7) 0.2604(4) 0.3014(4) 0.0759(12) Uani 1 1 d . .
N1 N 0.8502(7) 0.1721(4) 0.2661(4) 0.1068(15) Uani 1 1 d . .
N2 N 0.7620(4) 0.5236(2) 0.6133(2) 0.0568(8) Uani 1 1 d . .
H2 H 0.7915 0.4816 0.6707 0.068 Uiso 1 1 calc R U
Se1 Se 0.58252(8) 0.82437(4) 0.47017(5) 0.0967(3) 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'
Se Se -0.0929 2.2259 '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
Se1 C1 H1A 109.5
Se1 C1 H1B 109.5
H1A C1 H1B 109.5
Se1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C9 C2 C3 106.6(3)
C9 C2 Se1 125.8(3)
C3 C2 Se1 127.5(3)
C4 C3 C8 119.2(3)
C4 C3 C2 134.6(3)
C8 C3 C2 106.2(3)
C5 C4 C3 119.2(4)
C5 C4 H4 120.4
C3 C4 H4 120.4
C4 C5 C6 120.3(4)
C4 C5 H5 119.8
C6 C5 H5 119.8
C7 C6 C5 121.6(4)
C7 C6 C10 119.0(4)
C5 C6 C10 119.4(4)
C8 C7 C6 117.3(3)
C8 C7 H7 121.3
C6 C7 H7 121.3
N2 C8 C7 129.6(3)
N2 C8 C3 108.0(3)
C7 C8 C3 122.3(3)
C2 C9 N2 110.5(3)
C2 C9 H9 124.8
N2 C9 H9 124.8
N1 C10 C6 178.5(5)
C9 N2 C8 108.7(3)
C9 N2 H2 125.6
C8 N2 H2 125.6
C2 Se1 C1 99.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 Se1 1.918(6)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C9 1.359(6)
C2 C3 1.438(5)
C2 Se1 1.886(4)
C3 C4 1.393(5)
C3 C8 1.410(5)
C4 C5 1.377(6)
C4 H4 0.9300
C5 C6 1.410(6)
C5 H5 0.9300
C6 C7 1.381(5)
C6 C10 1.438(6)
C7 C8 1.380(5)
C7 H7 0.9300
C8 N2 1.370(4)
C9 N2 1.362(5)
C9 H9 0.9300
C10 N1 1.138(5)
N2 H2 0.8600
