#------------------------------------------------------------------------------
#$Date: 2017-07-08 11:44:22 +0200 (Sat 08 de Jul de 2017) $
#$Revision: 198567 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/86/7228661.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_7228661
loop_
_publ_author_name
'Lippolis, Vito'
'Aragoni, Maria Carla'
'Arca, Massimiliano'
'Isaia, Francesco'
'Demartin, Francesco'
'Bauza, Antonio'
'Frontera, Antonio'
'Montis, Riccardo'
_publ_section_title
;
 Hydrogen- and halogen-bond cooperativity in determining the crystal
 packing of dihalogen Charge-Transfer adducts: a study case from
 heterocyclic pentatomic chalcogenone donors
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01035D
_journal_year                    2017
_chemical_formula_sum            'C5 H8 Br I N2 O S'
_chemical_formula_weight         350.99
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-03-07 deposited with the CCDC.
2017-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                62.62(4)
_cell_angle_beta                 89.52(4)
_cell_angle_gamma                66.88(4)
_cell_formula_units_Z            2
_cell_length_a                   7.786(3)
_cell_length_b                   8.719(4)
_cell_length_c                   9.403(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      14.65
_cell_measurement_theta_min      9.70
_cell_volume                     509.6(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf-Nonius CAD4 diffractometer'
_diffrn_measurement_method       'omega scan'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1588
_diffrn_reflns_theta_full        23.97
_diffrn_reflns_theta_max         23.97
_diffrn_reflns_theta_min         3.09
_diffrn_standards_decay_%        no
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  '3600 sec'
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    7.221
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   empirical
_exptl_crystal_colour            dark-orange
_exptl_crystal_density_diffrn    2.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pseudoprism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         2.028
_refine_diff_density_min         -1.749
_refine_diff_density_rms         0.513
_refine_ls_extinction_coef       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.323
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.323
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1313P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1864
_reflns_number_gt                1413
_reflns_number_total             1588
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce01035d2.cif
_cod_data_source_block           Compound-1
_cod_original_cell_volume        509.6(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7228661
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I I 0.15670(7) 0.62966(7) 0.02361(6) 0.0334(4) Uani 1 1 d .
Br Br 0.28146(16) 0.52442(17) -0.20587(13) 0.0489(5) Uani 1 1 d .
S S 0.0010(4) 0.7345(4) 0.2276(4) 0.0449(7) Uani 1 1 d .
O O 0.2271(9) 1.0270(10) 0.4806(8) 0.0406(16) Uani 1 1 d .
N2 N 0.3133(10) 0.8005(10) 0.2473(9) 0.0318(16) Uani 1 1 d .
H2 H 0.3686 0.7535 0.1874 0.038 Uiso 1 1 calc R
N1 N 0.0945(9) 0.9002(10) 0.3716(9) 0.0319(16) Uani 1 1 d .
H1 H -0.0111 0.9238 0.4051 0.038 Uiso 1 1 calc R
C1 C 0.1451(11) 0.8120(12) 0.2801(11) 0.0317(19) Uani 1 1 d .
C2 C 0.2329(13) 0.9470(12) 0.4040(10) 0.0334(19) Uani 1 1 d .
C3 C 0.3965(12) 0.8768(12) 0.3242(11) 0.033(2) Uani 1 1 d .
C31 C 0.4364(13) 1.0401(13) 0.1995(11) 0.039(2) Uani 1 1 d .
H31A H 0.3225 1.1368 0.1170 0.059 Uiso 1 1 calc R
H31B H 0.5360 0.9917 0.1493 0.059 Uiso 1 1 calc R
H31C H 0.4760 1.0950 0.2534 0.059 Uiso 1 1 calc R
C32 C 0.5720(13) 0.7182(14) 0.4578(12) 0.038(2) Uani 1 1 d .
H32A H 0.5414 0.6173 0.5333 0.057 Uiso 1 1 calc R
H32B H 0.6127 0.7691 0.5152 0.057 Uiso 1 1 calc R
H32C H 0.6729 0.6678 0.4096 0.057 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I 0.0303(6) 0.0378(6) 0.0408(6) -0.0259(4) 0.0079(3) -0.0151(4)
Br 0.0491(8) 0.0601(8) 0.0478(7) -0.0366(6) 0.0222(5) -0.0218(6)
S 0.0342(14) 0.0709(18) 0.0630(17) -0.0529(15) 0.0206(13) -0.0298(13)
O 0.037(4) 0.061(4) 0.057(4) -0.049(4) 0.021(3) -0.028(3)
N2 0.030(4) 0.045(4) 0.039(4) -0.033(3) 0.017(3) -0.020(3)
N1 0.022(4) 0.042(4) 0.047(4) -0.034(4) 0.009(3) -0.013(3)
C1 0.022(4) 0.033(4) 0.043(5) -0.025(4) 0.006(4) -0.008(3)
C2 0.031(4) 0.039(5) 0.037(5) -0.026(4) 0.013(4) -0.013(4)
C3 0.028(5) 0.038(5) 0.049(5) -0.029(4) 0.021(4) -0.019(4)
C31 0.043(5) 0.038(5) 0.039(5) -0.018(4) 0.005(4) -0.020(4)
C32 0.031(5) 0.048(5) 0.049(5) -0.030(4) 0.014(4) -0.023(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
S I Br 173.43(6)
C1 S I 104.5(3)
C1 N2 C3 112.8(7)
C1 N1 C2 111.7(7)
N2 C1 N1 109.0(7)
N2 C1 S 130.1(7)
N1 C1 S 120.9(6)
O C2 N1 126.5(8)
O C2 C3 126.6(8)
N1 C2 C3 106.9(7)
N2 C3 C31 112.4(7)
N2 C3 C32 111.4(7)
C31 C3 C32 112.0(7)
N2 C3 C2 99.6(6)
C31 C3 C2 111.8(7)
C32 C3 C2 108.8(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I S 2.587(3)
I Br 2.7436(16)
S C1 1.694(8)
O C2 1.201(10)
N2 C1 1.319(11)
N2 C3 1.475(11)
N1 C1 1.362(10)
N1 C2 1.372(12)
C2 C3 1.535(11)
C3 C31 1.517(12)
C3 C32 1.518(13)
