#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:07:42 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230383 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/71/7057156.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_7057156
loop_
_publ_author_name
'Montis, Riccardo'
'Arca, Massimiliano'
'Aragoni, M. Carla'
'Blake, Alexander J.'
'Castellano, Carlo'
'Demartin, Francesco'
'Isaia, Francesco'
'Lippolis, Vito'
'Pintus, Anna'
'Lenardão, Eder J.'
'Perin, Gelson'
'O'Connor, Alice E.'
'Thurow, Samuel'
_publ_section_title
;
 Structural diversity in the products formed by the reactions of
 2-arylselanyl pyridine derivatives and dihalogens
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10592
_journal_paper_doi               10.1039/C8NJ00495A
_journal_volume                  42
_journal_year                    2018
_chemical_formula_sum            'C11 H8 Br Cl I N Se'
_chemical_formula_weight         475.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2018-03-06 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                104.07(3)
_cell_angle_beta                 107.51(3)
_cell_angle_gamma                103.00(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8181(16)
_cell_length_b                   9.764(2)
_cell_length_c                   10.419(2)
_cell_measurement_reflns_used    5289
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      31.09
_cell_measurement_theta_min      2.17
_cell_volume                     696.5(4)
_computing_data_reduction        'Bruker AXS SAINT software'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measurement_device_type  'APEX II CCD diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7466
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         31.753
_diffrn_reflns_theta_min         2.175
_exptl_absorpt_coefficient_mu    7.945
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Area-Detector Absorption Correction Program, 
Bruker AXS Inc., Madison, Wisconsin, USA, 2000
Rint for all data  0.145 with corrections  0.025
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.267
_exptl_crystal_description       pseudoprism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   1.000
_exptl_transmission_factor_min   0.540
_refine_diff_density_max         1.082
_refine_diff_density_min         -0.832
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         4244
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0364P)²+1.0280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0866
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3667
_reflns_number_total             4244
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj00495a2.cif
_cod_data_source_block           L1IBr
_cod_depositor_comments
'Adding full bibliography for 7057153--7057162.cif.'
_cod_original_cell_volume        696.5(3)
_cod_database_code               7057156
_shelx_shelxl_version_number     2017/1
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.5701(4) 0.3652(3) 0.6811(4) 0.0352(6) Uani 1 1 d . .
N N 0.6930(4) 0.4352(3) 0.6336(3) 0.0384(6) Uani 1 1 d . .
C3 C 0.8402(6) 0.5550(5) 0.7232(5) 0.0556(10) Uani 1 1 d . .
H3 H 0.924460 0.602101 0.688479 0.067 Uiso 1 1 calc R U
C4 C 0.8702(7) 0.6101(6) 0.8646(5) 0.0689(14) Uani 1 1 d . .
H4 H 0.972657 0.694448 0.925256 0.083 Uiso 1 1 calc R U
C5 C 0.7458(7) 0.5386(5) 0.9162(5) 0.0633(12) Uani 1 1 d . .
H5 H 0.764896 0.573276 1.012416 0.076 Uiso 1 1 calc R U
C6 C 0.5935(6) 0.4156(4) 0.8234(4) 0.0474(8) Uani 1 1 d . .
H6 H 0.507476 0.366964 0.855941 0.057 Uiso 1 1 calc R U
C7 C 0.2131(5) 0.1558(4) 0.6482(4) 0.0407(7) Uani 1 1 d . .
C8 C 0.2330(6) 0.0567(5) 0.7213(5) 0.0520(9) Uani 1 1 d . .
H8 H 0.331675 0.017036 0.727997 0.062 Uiso 1 1 calc R U
C9 C 0.1065(6) 0.0157(5) 0.7848(5) 0.0541(10) Uani 1 1 d . .
H9 H 0.119665 -0.051006 0.834418 0.065 Uiso 1 1 calc R U
C10 C -0.0387(5) 0.0751(4) 0.7734(4) 0.0448(8) Uani 1 1 d . .
C11 C -0.0582(6) 0.1740(5) 0.7019(6) 0.0585(11) Uani 1 1 d . .
H11 H -0.156786 0.213717 0.695441 0.070 Uiso 1 1 calc R U
C12 C 0.0677(6) 0.2152(5) 0.6392(5) 0.0555(10) Uani 1 1 d . .
H12 H 0.054609 0.283037 0.590765 0.067 Uiso 1 1 calc R U
Cl Cl -0.20406(17) 0.01872(16) 0.84649(13) 0.0697(3) Uani 1 1 d . .
Se Se 0.36825(6) 0.19547(5) 0.54055(4) 0.05300(12) Uani 1 1 d . .
Br Br 0.62193(7) 0.25258(6) 0.11915(5) 0.06453(14) Uani 1 1 d . .
I I 0.66242(3) 0.34981(2) 0.38787(3) 0.04034(8) 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'
Cl Cl 0.1484 0.1585 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
N C1 C6 120.7(3)
N C1 Se 115.3(2)
C6 C1 Se 124.0(3)
C3 N C1 120.3(3)
C3 N I 117.6(3)
C1 N I 122.1(2)
N C3 C4 121.7(4)
C3 C4 C5 119.0(4)
C6 C5 C4 119.2(4)
C5 C6 C1 119.1(4)
C8 C7 C12 119.8(4)
C8 C7 Se 120.7(3)
C12 C7 Se 119.1(3)
C7 C8 C9 120.2(4)
C10 C9 C8 119.1(4)
C11 C10 C9 120.9(4)
C11 C10 Cl 119.7(3)
C9 C10 Cl 119.4(3)
C10 C11 C12 120.2(4)
C11 C12 C7 119.9(4)
C1 Se C7 100.00(14)
N I Br 178.74(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N 1.337(4)
C1 C6 1.384(5)
C1 Se 1.906(3)
N C3 1.335(5)
N I 2.410(3)
C3 C4 1.365(7)
C4 C5 1.383(7)
C5 C6 1.376(6)
C7 C8 1.377(5)
C7 C12 1.377(6)
C7 Se 1.923(4)
C8 C9 1.386(6)
C9 C10 1.374(6)
C10 C11 1.363(6)
C10 Cl 1.741(4)
C11 C12 1.377(6)
Br I 2.6229(9)
