#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:08:22 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230387 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/74/7057461.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_7057461
loop_
_publ_author_name
'Lee, Jiwon'
'Lee, Lucia Myongwon'
'Arnott, Zachary'
'Jenkins, Hilary'
'Britten, James F.'
'Vargas-Baca, Ignacio'
_publ_section_title
;
 Sigma-hole interactions in the molecular and crystal structures of
 N-boryl benzo-2,1,3-selenadiazoles
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10555
_journal_paper_doi               10.1039/C8NJ00553B
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C6 H4 B Cl3 N2 Se'
_chemical_formula_sum            'C6 H4 B Cl3 N2 Se'
_chemical_formula_weight         300.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-01-29 deposited with the CCDC.
2018-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.332(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3016(12)
_cell_length_b                   7.2586(6)
_cell_length_c                   10.0368(8)
_cell_measurement_reflns_used    9558
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      36.267
_cell_measurement_theta_min      2.801
_cell_volume                     981.23(14)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_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  0.0161
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16583
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         36.382
_diffrn_reflns_theta_min         2.801
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.591
_exptl_absorpt_correction_T_max  0.7415
_exptl_absorpt_correction_T_min  0.5876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0407 before and 0.0250 after correction.
The Ratio of minimum to maximum transmission is 0.7924.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.032
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.108
_refine_diff_density_max         0.832
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         2528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0180
_refine_ls_R_factor_gt           0.0164
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0378P)²+0.0057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0475
_refine_ls_wR_factor_ref         0.0481
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2398
_reflns_number_total             2528
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj00553b2.cif
_cod_data_source_block           jl008_0m_a
_cod_depositor_comments
'Adding full bibliography for 7057460--7057464.cif.'
_cod_database_code               7057461
_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_max   0.637
_shelx_estimated_absorpt_t_min   0.516
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C5(H5), C3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
_atom_site_refinement_flags_occupancy
Se1 Se 0.86781(2) 0.5000 0.96159(2) 0.01112(4) Uani 1 2 d S T P
Cl02 Cl 0.68961(2) 0.5000 1.02338(3) 0.01566(5) Uani 1 2 d S T P
Cl03 Cl 0.57485(2) 0.29157(2) 0.72729(2) 0.01495(4) Uani 1 1 d . . .
N1 N 0.74419(6) 0.5000 0.79868(9) 0.01142(14) Uani 1 2 d S T P
N2 N 0.92225(6) 0.5000 0.84092(10) 0.01231(14) Uani 1 2 d S T P
C1 C 0.75031(7) 0.5000 0.66936(10) 0.01075(15) Uani 1 2 d S T P
C4 C 0.79260(8) 0.5000 0.42727(12) 0.01464(17) Uani 1 2 d S T P
H4 H 0.8044 0.5000 0.3445 0.018 Uiso 1 2 calc RS T P
C6 C 0.66988(7) 0.5000 0.51928(11) 0.01357(16) Uani 1 2 d S T P
H6 H 0.6044 0.5000 0.5013 0.016 Uiso 1 2 calc RS T P
C5 C 0.69204(8) 0.5000 0.40267(11) 0.01495(17) Uani 1 2 d S T P
H5 H 0.6403 0.5000 0.3039 0.018 Uiso 1 2 calc RS T P
C2 C 0.85171(7) 0.5000 0.69528(11) 0.01082(15) Uani 1 2 d S T P
C3 C 0.87113(7) 0.5000 0.57028(11) 0.01321(16) Uani 1 2 d S T P
H3 H 0.9360 0.5000 0.5854 0.016 Uiso 1 2 calc RS T P
B1 B 0.64823(8) 0.5000 0.81705(12) 0.01217(17) Uani 1 2 d S T P
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'
B B 0.0013 0.0007 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 Se1 N1 90.64(4) . .
C1 N1 Se1 110.38(6) . .
C1 N1 B1 127.80(8) . .
B1 N1 Se1 121.83(7) . .
C2 N2 Se1 110.45(7) . .
N1 C1 C6 126.90(9) . .
N1 C1 C2 112.73(8) . .
C6 C1 C2 120.37(9) . .
C5 C4 H4 119.5 . .
C3 C4 H4 119.5 . .
C3 C4 C5 121.08(9) . .
C1 C6 H6 121.1 . .
C5 C6 C1 117.77(9) . .
C5 C6 H6 121.1 . .
C4 C5 H5 118.9 . .
C6 C5 C4 122.28(9) . .
C6 C5 H5 118.9 . .
N2 C2 C1 115.79(9) . .
N2 C2 C3 124.37(9) . .
C3 C2 C1 119.84(8) . .
C4 C3 C2 118.66(9) . .
C4 C3 H3 120.7 . .
C2 C3 H3 120.7 . .
Cl03 B1 Cl02 110.57(4) 6_565 .
Cl03 B1 Cl02 110.57(4) . .
Cl03 B1 Cl03 110.24(5) 6_565 .
N1 B1 Cl02 106.81(6) . .
N1 B1 Cl03 109.29(5) . .
N1 B1 Cl03 109.29(5) . 6_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 N1 1.8210(8) .
Se1 N2 1.7659(9) .
Cl02 B1 1.8560(11) .
Cl03 B1 1.8442(6) .
N1 C1 1.3450(13) .
N1 B1 1.5643(14) .
N2 C2 1.3432(13) .
C1 C6 1.4227(14) .
C1 C2 1.4463(13) .
C4 H4 0.9300 .
C4 C5 1.4380(15) .
C4 C3 1.3665(15) .
C6 H6 0.9300 .
C6 C5 1.3644(15) .
C5 H5 0.9300 .
C2 C3 1.4199(14) .
C3 H3 0.9300 .
B1 Cl03 1.8442(6) 6_565
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_4
Se1 N1 C1 C6 180.000(0) .
Se1 N1 C1 C2 0.000(0) .
Se1 N1 B1 Cl02 0.000(0) .
Se1 N1 B1 Cl03 119.64(4) 6_565
Se1 N1 B1 Cl03 -119.64(4) .
Se1 N2 C2 C1 0.000(0) .
Se1 N2 C2 C3 180.000(0) .
N1 Se1 N2 C2 0.000(0) .
N1 C1 C6 C5 180.000(0) .
N1 C1 C2 N2 0.000(0) .
N1 C1 C2 C3 180.000(0) .
N2 Se1 N1 C1 0.000(0) .
N2 Se1 N1 B1 180.000(0) .
N2 C2 C3 C4 180.000(0) .
C1 N1 B1 Cl02 180.000(0) .
C1 N1 B1 Cl03 -60.36(4) 6_565
C1 N1 B1 Cl03 60.36(4) .
C1 C6 C5 C4 0.000(0) .
C1 C2 C3 C4 0.000(0) .
C6 C1 C2 N2 180.000(0) .
C6 C1 C2 C3 0.000(0) .
C5 C4 C3 C2 0.000(0) .
C2 C1 C6 C5 0.000(0) .
C3 C4 C5 C6 0.000(0) .
B1 N1 C1 C6 0.000(1) .
B1 N1 C1 C2 180.000(0) .
