#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:24:46 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180337 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/06/7200692.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_7200692
loop_
_publ_author_name
'Berionni, Guillaume'
'Pégot, Bruce'
'Marrot, Jérome'
'Goumont, Régis'
_publ_section_title
;
 Supramolecular association of 1,2,5-chalcogenadiazoles: an unexpected
 self-assembled dissymetric [Se⋯N]2 four-membered ring
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              986
_journal_paper_doi               10.1039/b820258c
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C20 H18 B2 F8 N6 Se3'
_chemical_formula_weight         752.90
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.711(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.8892(4)
_cell_length_b                   12.0225(4)
_cell_length_c                   13.5325(4)
_cell_measurement_reflns_used    8577
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.68
_cell_measurement_theta_min      2.56
_cell_volume                     2584.89(13)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 512x512
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            49871
_diffrn_reflns_theta_full        30.10
_diffrn_reflns_theta_max         30.10
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    4.351
_exptl_absorpt_correction_T_max  0.6233
_exptl_absorpt_correction_T_min  0.2750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2.10)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.287
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.234
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1050P)²+5.7251P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1698
_reflns_number_gt                2911
_reflns_number_total             3791
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b820258c.txt
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7200692
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.59067(12) 0.57469(17) 1.07823(14) 0.0448(5) Uani 1 1 d . . .
Se2A Se 0.630877(14) 0.45163(2) 1.025311(17) 0.04630(6) Uani 1 1 d . . .
N3A N 0.68005(12) 0.53730(16) 0.92816(14) 0.0431(5) Uani 1 1 d . . .
C4A C 0.68850(14) 0.7355(2) 0.88106(16) 0.0477(6) Uani 1 1 d . . .
H4A H 0.7214 0.7242 0.8256 0.057 Uiso 1 1 calc R . .
C5A C 0.66367(16) 0.8387(2) 0.9078(2) 0.0566(7) Uani 1 1 d . . .
H5A H 0.6801 0.8990 0.8697 0.068 Uiso 1 1 calc R . .
C6A C 0.61256(17) 0.8583(2) 0.9933(2) 0.0564(7) Uani 1 1 d . . .
H6A H 0.5957 0.9305 1.0080 0.068 Uiso 1 1 calc R . .
C7A C 0.58860(16) 0.7736(2) 1.0526(2) 0.0530(6) Uani 1 1 d . . .
H7A H 0.5576 0.7872 1.1092 0.064 Uiso 1 1 calc R . .
C8A C 0.61178(13) 0.6642(2) 1.02675(16) 0.0424(5) Uani 1 1 d . . .
C9A C 0.66267(13) 0.64506(19) 0.94056(15) 0.0405(5) Uani 1 1 d . . .
C10A C 0.73134(17) 0.4906(3) 0.8486(2) 0.0600(7) Uani 1 1 d . . .
H10A H 0.7108 0.5172 0.7860 0.090 Uiso 1 1 calc R . .
H10B H 0.7279 0.4109 0.8501 0.090 Uiso 1 1 calc R . .
H10C H 0.7889 0.5131 0.8578 0.090 Uiso 1 1 calc R . .
N1B N 0.54628(12) 0.37766(17) 1.17231(14) 0.0457(5) Uani 1 1 d . . .
Se2B Se 0.5000 0.48209(3) 1.2500 0.04755(8) Uani 1 2 d S . .
C6B C 0.52608(17) 0.0801(2) 1.2073(2) 0.0561(7) Uani 1 1 d . . .
H6B H 0.5424 0.0124 1.1803 0.067 Uiso 1 1 calc R . .
C7B C 0.55227(15) 0.1751(2) 1.16487(17) 0.0502(6) Uani 1 1 d . . .
H7B H 0.5865 0.1734 1.1097 0.060 Uiso 1 1 calc R . .
C8B C 0.52641(13) 0.27838(19) 1.20634(14) 0.0400(5) Uani 1 1 d . . .
B B 0.6560(2) 0.1796(3) 0.8688(2) 0.0607(8) Uani 1 1 d . . .
F1 F 0.73852(17) 0.2004(3) 0.8410(2) 0.1442(12) Uani 1 1 d . . .
F2 F 0.6548(3) 0.1237(4) 0.9536(3) 0.2095(19) Uani 1 1 d . . .
F3 F 0.6145(2) 0.2731(2) 0.8746(4) 0.1722(16) Uani 1 1 d . . .
F4 F 0.6269(4) 0.1163(3) 0.8012(3) 0.235(2) 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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
C8A N1A Se2A 111.80(15) . . ?
C8A N1A Se2B 147.54(15) . . ?
Se2A N1A Se2B 100.66(8) . . ?
N1A Se2A N3A 88.85(9) . . ?
N1A Se2A N1B 77.35(8) . . ?
N3A Se2A N1B 166.09(8) . . ?
N1A Se2A F3 148.71(9) . . ?
N3A Se2A F3 87.05(10) . . ?
N1B Se2A F3 103.82(9) . . ?
C9A N3A C10A 125.5(2) . . ?
C9A N3A Se2A 111.15(15) . . ?
C10A N3A Se2A 123.39(17) . . ?
C5A C4A C9A 117.7(2) . . ?
C5A C4A H4A 121.2 . . ?
C9A C4A H4A 121.2 . . ?
C4A C5A C6A 122.3(2) . . ?
C4A C5A H5A 118.9 . . ?
C6A C5A H5A 118.9 . . ?
C7A C6A C5A 121.2(3) . . ?
C7A C6A H6A 119.4 . . ?
C5A C6A H6A 119.4 . . ?
C6A C7A C8A 118.5(2) . . ?
C6A C7A H7A 120.7 . . ?
C8A C7A H7A 120.7 . . ?
N1A C8A C7A 123.8(2) . . ?
N1A C8A C9A 116.2(2) . . ?
C7A C8A C9A 120.0(2) . . ?
N3A C9A C4A 127.7(2) . . ?
N3A C9A C8A 112.00(19) . . ?
C4A C9A C8A 120.3(2) . . ?
N3A C10A H10A 109.5 . . ?
N3A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
N3A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C8B N1B Se2B 109.02(14) . . ?
C8B N1B Se2A 135.41(15) . . ?
Se2B N1B Se2A 115.56(10) . . ?
N1B Se2B N1B 91.57(13) . 2_657 ?
N1B Se2B N1A 66.32(8) . . ?
N1B Se2B N1A 157.67(8) 2_657 . ?
C7B C6B C6B 121.97(15) . 2_657 ?
C7B C6B H6B 119.0 . . ?
C6B C6B H6B 119.0 2_657 . ?
C6B C7B C8B 118.6(2) . . ?
C6B C7B H7B 120.7 . . ?
C8B C7B H7B 120.7 . . ?
N1B C8B C7B 125.41(19) . . ?
N1B C8B C8B 115.19(12) . 2_657 ?
C7B C8B C8B 119.40(13) . 2_657 ?
F4 B F3 112.2(4) . . ?
F4 B F2 108.0(4) . . ?
F3 B F2 111.8(4) . . ?
F4 B F1 104.4(4) . . ?
F3 B F1 109.8(3) . . ?
F2 B F1 110.4(4) . . ?
B F3 Se2A 128.5(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C8A 1.328(3) . ?
N1A Se2A 1.767(2) . ?
N1A Se2B 2.9666(19) . ?
Se2A N3A 1.8507(19) . ?
Se2A N1B 2.5732(19) . ?
Se2A F3 2.970(4) . ?
N3A C9A 1.336(3) . ?
N3A C10A 1.470(3) . ?
C4A C5A 1.352(4) . ?
C4A C9A 1.416(3) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.441(4) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.355(4) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.410(4) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.446(3) . ?
C10A H10A 0.9600 . ?
C10A H10B 0.9600 . ?
C10A H10C 0.9600 . ?
N1B C8B 1.319(3) . ?
N1B Se2B 1.800(2) . ?
Se2B N1B 1.800(2) 2_657 ?
C6B C7B 1.347(4) . ?
C6B C6B 1.431(6) 2_657 ?
C6B H6B 0.9300 . ?
C7B C8B 1.425(3) . ?
C7B H7B 0.9300 . ?
C8B C8B 1.458(4) 2_657 ?
B F4 1.273(5) . ?
B F3 1.305(4) . ?
B F2 1.329(5) . ?
B F1 1.391(4) . ?
