#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:46:13 +0300 (Mon, 04 May 2020) $
#$Revision: 251478 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038253.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_4038253
loop_
_publ_author_name
'Matsubara, Ryosuke'
'Ando, Akihiro'
'Hasebe, Hayu'
'Kim, Hojin'
'Tsuneda, Takao'
'Hayashi, Masahiko'
_publ_section_title
;
 Synthesis and Synthetic Application of Chloro- and Bromofuroxans.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5959
_journal_page_last               5972
_journal_paper_doi               10.1021/acs.joc.0c00326
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C10 H6 Cl2 N2 O2'
_chemical_formula_sum            'C10 H6 Cl2 N2 O2'
_chemical_formula_weight         257.08
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_cell_angle_alpha                112.164(5)
_cell_angle_beta                 95.909(6)
_cell_angle_gamma                103.111(5)
_cell_formula_units_Z            2
_cell_length_a                   5.5643(19)
_cell_length_b                   9.865(4)
_cell_length_c                   10.798(4)
_cell_measurement_reflns_used    802
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.328
_cell_volume                     522.8(3)
_computing_cell_refinement       Unknown
_computing_data_collection       Unknown
_computing_data_reduction        Unknown
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      90
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2303
_diffrn_reflns_theta_full        23.82
_diffrn_reflns_theta_max         23.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            NONE
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NONE
_exptl_crystal_F_000             260.00
_exptl_crystal_size_max          0.331
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1590
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0377P)²+0.0569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0889
_reflns_number_gt                1261
_reflns_number_total             1590
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo0c00326_si_008.cif
_cod_data_source_block           AA1010_PTLC_b_0am
_cod_depositor_comments
'Adding full bibliography for 4038245--4038253.cif.'
_cod_original_cell_volume        522.8(4)
_cod_database_code               4038253
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.38545(13) 0.26090(8) -0.16471(8) 0.0176(3) Uani 1.0 2 d . . .
Cl2 Cl -0.24604(14) 0.02780(8) -0.38089(9) 0.0225(3) Uani 1.0 2 d . . .
O1 O -0.1668(4) 0.0931(2) -0.0667(3) 0.0170(5) Uani 1.0 2 d . . .
O13 O 0.0844(4) -0.2638(3) -0.3757(3) 0.0226(6) Uani 1.0 2 d . . .
N11 N -0.0966(5) -0.2169(3) -0.4345(3) 0.0210(7) Uani 1.0 2 d . . .
N12 N 0.2252(5) -0.1475(3) -0.2531(3) 0.0171(6) Uani 1.0 2 d . . .
C2 C 0.0877(6) 0.5433(4) 0.2546(4) 0.0186(8) Uani 1.0 2 d . . .
C3 C 0.3739(6) 0.3402(4) 0.1877(4) 0.0149(7) Uani 1.0 2 d . . .
C4 C 0.3103(6) 0.5712(4) 0.3438(4) 0.0174(8) Uani 1.0 2 d . . .
C5 C 0.1349(6) -0.0325(3) -0.2338(4) 0.0132(7) Uani 1.0 2 d . . .
C6 C 0.1487(5) 0.3100(3) 0.0992(3) 0.0112(7) Uani 1.0 2 d . . .
C7 C 0.4519(6) 0.4686(4) 0.3096(4) 0.0183(8) Uani 1.0 2 d . . .
C8 C 0.0047(6) 0.4137(3) 0.1343(4) 0.0146(7) Uani 1.0 2 d . . .
C9 C -0.0630(6) -0.0767(3) -0.3478(4) 0.0142(7) Uani 1.0 2 d . . .
C10 C 0.2470(6) 0.1135(3) -0.1111(4) 0.0126(7) Uani 1.0 2 d . . .
C14 C 0.0526(6) 0.1679(3) -0.0270(4) 0.0128(7) Uani 1.0 2 d . . .
H2 H -0.0069 0.6133 0.2806 0.0298 Uiso 1.0 2 calc R . .
H3 H 0.4726 0.2683 0.1664 0.0095 Uiso 1.0 2 calc R . .
H4 H 0.3637 0.6581 0.4258 0.0208 Uiso 1.0 2 calc R . .
H7 H 0.6002 0.4864 0.3692 0.0219 Uiso 1.0 2 calc R . .
H8 H -0.1462 0.3949 0.0762 0.0175 Uiso 1.0 2 calc R . .
H10 H 0.3794 0.1011 -0.0526 0.0151 Uiso 1.0 2 calc R . .
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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, 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_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N11 O13 N12 110.9(2) yes . . .
O13 N11 C9 103.8(3) yes . . .
O13 N12 C5 106.4(3) yes . . .
C4 C2 C8 120.7(4) yes . . .
C6 C3 C7 120.4(3) yes . . .
C2 C4 C7 119.6(3) yes . . .
N12 C5 C9 107.6(3) yes . . .
N12 C5 C10 120.4(3) yes . . .
C9 C5 C10 132.0(3) yes . . .
C3 C6 C8 119.2(3) yes . . .
C3 C6 C14 121.3(3) yes . . .
C8 C6 C14 119.4(3) yes . . .
C3 C7 C4 120.3(3) yes . . .
C2 C8 C6 119.8(3) yes . . .
Cl2 C9 N11 119.9(3) yes . . .
Cl2 C9 C5 128.8(3) yes . . .
N11 C9 C5 111.3(3) yes . . .
Cl1 C10 C5 108.9(3) yes . . .
Cl1 C10 C14 107.4(3) yes . . .
C5 C10 C14 113.3(3) yes . . .
O1 C14 C6 123.8(3) yes . . .
O1 C14 C10 119.1(3) yes . . .
C6 C14 C10 117.1(3) yes . . .
C4 C2 H2 118.150 no . . .
C8 C2 H2 121.103 no . . .
C6 C3 H3 120.221 no . . .
C7 C3 H3 119.293 no . . .
C2 C4 H4 120.218 no . . .
C7 C4 H4 120.210 no . . .
C3 C7 H7 119.858 no . . .
C4 C7 H7 119.852 no . . .
C2 C8 H8 120.113 no . . .
C6 C8 H8 120.124 no . . .
Cl1 C10 H10 109.027 no . . .
C5 C10 H10 109.024 no . . .
C14 C10 H10 109.032 no . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Cl1 C10 1.806(4) yes . .
Cl2 C9 1.705(4) yes . .
O1 C14 1.210(4) yes . .
O13 N11 1.390(4) yes . .
O13 N12 1.385(3) yes . .
N11 C9 1.301(4) yes . .
N12 C5 1.298(5) yes . .
C2 C4 1.391(5) yes . .
C2 C8 1.375(4) yes . .
C3 C6 1.394(5) yes . .
C3 C7 1.379(4) yes . .
C4 C7 1.386(5) yes . .
C5 C9 1.420(5) yes . .
C5 C10 1.484(4) yes . .
C6 C8 1.405(5) yes . .
C6 C14 1.475(4) yes . .
C10 C14 1.543(5) yes . .
C2 H2 0.939 no . .
C3 H3 0.967 no . .
C4 H4 0.930 no . .
C7 H7 0.930 no . .
C8 H8 0.930 no . .
C10 H10 0.980 no . .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Cl1 C3 3.595(4) no . .
Cl1 C6 3.180(4) no . .
Cl1 C9 3.387(3) no . .
Cl2 O1 3.167(3) no . .
Cl2 C10 3.489(4) no . .
Cl2 C14 3.597(4) no . .
O1 C3 3.530(3) no . .
O1 C5 2.737(4) no . .
O1 C8 2.941(3) no . .
O1 C9 3.053(4) no . .
O13 C10 3.571(3) no . .
N12 C14 3.559(4) no . .
C2 C3 2.769(5) no . .
C3 C10 3.046(4) no . .
C4 C6 2.784(4) no . .
C7 C8 2.778(5) no . .
C9 C14 3.282(4) no . .
Cl1 O1 3.566(3) no . 1_655
Cl1 C2 3.564(4) no . 2_665
Cl1 C4 3.342(4) no . 2_665
Cl1 C7 3.569(4) no . 2_665
Cl2 Cl2 3.4119(15) no . 2_454
O1 Cl1 3.566(3) no . 1_455
O1 O1 3.449(4) no . 2_555
O1 N12 3.532(3) no . 1_455
O1 N12 3.351(4) no . 2_555
O1 C5 3.509(5) no . 2_555
O1 C10 3.310(4) no . 1_455
O1 C10 3.280(5) no . 2_555
O1 C14 3.261(5) no . 2_555
O13 C2 3.465(5) no . 2_555
O13 C3 3.541(5) no . 2_555
O13 C4 3.376(5) no . 1_544
O13 C4 3.473(5) no . 2_555
O13 C6 3.515(5) no . 2_555
O13 C7 3.505(4) no . 2_555
O13 C8 3.475(5) no . 2_555
N11 C4 3.530(4) no . 1_444
N11 C7 3.484(4) no . 1_444
N11 C7 3.569(5) no . 2_555
N12 O1 3.532(3) no . 1_655
N12 O1 3.351(4) no . 2_555
N12 C3 3.420(5) no . 2_655
N12 C6 3.296(5) no . 2_555
N12 C8 3.396(5) no . 2_555
N12 C14 3.585(5) no . 2_555
C2 Cl1 3.564(4) no . 2_665
C2 O13 3.465(5) no . 2_555
C3 O13 3.541(5) no . 2_555
C3 N12 3.420(5) no . 2_655
C3 C8 3.571(5) no . 1_655
C4 Cl1 3.342(4) no . 2_665
C4 O13 3.376(5) no . 1_566
C4 O13 3.473(5) no . 2_555
C4 N11 3.530(4) no . 1_666
C5 O1 3.509(5) no . 2_555
C6 O13 3.515(5) no . 2_555
C6 N12 3.296(5) no . 2_555
C7 Cl1 3.569(4) no . 2_665
C7 O13 3.505(4) no . 2_555
C7 N11 3.484(4) no . 1_666
C7 N11 3.569(5) no . 2_555
C8 O13 3.475(5) no . 2_555
C8 N12 3.396(5) no . 2_555
C8 C3 3.571(5) no . 1_455
C10 O1 3.310(4) no . 1_655
C10 O1 3.280(5) no . 2_555
C14 O1 3.261(5) no . 2_555
C14 N12 3.585(5) no . 2_555
C14 C14 3.507(5) no . 2_555
Cl1 H3 3.5290 no . .
O1 H8 2.7564 no . .
O1 H10 3.0090 no . .
N12 H10 2.4685 no . .
C2 H7 3.2401 no . .
C3 H4 3.2372 no . .
C3 H8 3.2555 no . .
C3 H10 2.7795 no . .
C4 H3 3.2672 no . .
C4 H8 3.2432 no . .
C6 H2 3.2620 no . .
C6 H7 3.2436 no . .
C6 H10 2.7686 no . .
C7 H2 3.2373 no . .
C8 H3 3.2924 no . .
C8 H4 3.2415 no . .
C9 H10 3.3923 no . .
C10 H3 2.7909 no . .
C14 H3 2.6810 no . .
C14 H8 2.6408 no . .
H2 H4 2.3027 no . .
H2 H8 2.3272 no . .
H3 H7 2.3157 no . .
H3 H10 2.2354 no . .
H4 H7 2.3173 no . .
Cl1 H2 3.0594 no . 2_565
Cl1 H4 3.5407 no . 2_665
Cl1 H8 3.1232 no . 1_655
Cl2 H2 3.1975 no . 2_565
Cl2 H4 3.4788 no . 1_444
Cl2 H4 3.5000 no . 2_565
O1 H3 3.5608 no . 1_455
O1 H3 3.2772 no . 2_555
O1 H10 2.5623 no . 1_455
O1 H10 2.8067 no . 2_555
O13 H2 3.3819 no . 1_544
O13 H3 3.1885 no . 2_655
O13 H4 2.7544 no . 1_544
O13 H7 3.3549 no . 1_444
O13 H7 3.1221 no . 2_655
N11 H2 3.0542 no . 1_544
N11 H4 2.9664 no . 1_444
N11 H4 3.3439 no . 1_544
N11 H7 2.8720 no . 1_444
N12 H3 2.5595 no . 2_655
N12 H4 3.5357 no . 1_544
N12 H7 3.5011 no . 2_655
N12 H10 3.5848 no . 2_655
C2 H7 3.1194 no . 1_455
C3 H8 3.0605 no . 1_655
C4 H7 3.3636 no . 2_666
C7 H2 3.1280 no . 1_655
C7 H7 3.3778 no . 2_666
C7 H8 3.5208 no . 1_655
C8 H3 3.0993 no . 1_455
C8 H7 3.5433 no . 1_455
C8 H8 3.5049 no . 2_565
C9 H4 3.5746 no . 1_444
C14 H10 3.5790 no . 2_555
H2 Cl1 3.0594 no . 2_565
H2 Cl2 3.1975 no . 2_565
H2 O13 3.3819 no . 1_566
H2 N11 3.0542 no . 1_566
H2 C7 3.1280 no . 1_455
H2 H7 2.7119 no . 1_455
H3 O1 3.5608 no . 1_655
H3 O1 3.2772 no . 2_555
H3 O13 3.1885 no . 2_655
H3 N12 2.5595 no . 2_655
H3 C8 3.0993 no . 1_655
H3 H8 2.6734 no . 1_655
H4 Cl1 3.5407 no . 2_665
H4 Cl2 3.4788 no . 1_666
H4 Cl2 3.5000 no . 2_565
H4 O13 2.7544 no . 1_566
H4 N11 3.3439 no . 1_566
H4 N11 2.9664 no . 1_666
H4 N12 3.5357 no . 1_566
H4 C9 3.5746 no . 1_666
H4 H7 3.0650 no . 2_666
H7 O13 3.3549 no . 1_666
H7 O13 3.1221 no . 2_655
H7 N11 2.8720 no . 1_666
H7 N12 3.5011 no . 2_655
H7 C2 3.1194 no . 1_655
H7 C4 3.3636 no . 2_666
H7 C7 3.3778 no . 2_666
H7 C8 3.5433 no . 1_655
H7 H2 2.7119 no . 1_655
H7 H4 3.0650 no . 2_666
H7 H7 3.0827 no . 2_666
H7 H8 3.4869 no . 1_655
H8 Cl1 3.1232 no . 1_455
H8 C3 3.0605 no . 1_455
H8 C7 3.5208 no . 1_455
H8 C8 3.5049 no . 2_565
H8 H3 2.6734 no . 1_455
H8 H7 3.4869 no . 1_455
H8 H8 3.3554 no . 2_565
H8 H10 3.1674 no . 1_455
H10 O1 2.5623 no . 1_655
H10 O1 2.8067 no . 2_555
H10 N12 3.5848 no . 2_655
H10 C14 3.5790 no . 2_555
H10 H8 3.1674 no . 1_655
H10 H10 3.1114 no . 2_655
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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N11 O13 N12 C5 0.9(4) no . . . .
N12 O13 N11 C9 -0.3(3) no . . . .
O13 N11 C9 Cl2 179.2(3) no . . . .
O13 N11 C9 C5 -0.4(4) no . . . .
O13 N12 C5 C9 -1.1(4) no . . . .
O13 N12 C5 C10 -179.1(3) no . . . .
C4 C2 C8 C6 -1.4(6) no . . . .
C8 C2 C4 C7 1.1(6) no . . . .
C6 C3 C7 C4 -1.7(6) no . . . .
C7 C3 C6 C8 1.4(5) no . . . .
C7 C3 C6 C14 -175.6(3) no . . . .
C2 C4 C7 C3 0.5(6) no . . . .
N12 C5 C9 Cl2 -178.5(3) no . . . .
N12 C5 C9 N11 1.0(4) no . . . .
N12 C5 C10 Cl1 115.1(4) no . . . .
N12 C5 C10 C14 -125.4(4) no . . . .
C9 C5 C10 Cl1 -62.3(5) no . . . .
C9 C5 C10 C14 57.2(5) no . . . .
C10 C5 C9 Cl2 -0.9(6) no . . . .
C10 C5 C9 N11 178.7(4) no . . . .
C3 C6 C8 C2 0.2(5) no . . . .
C3 C6 C14 O1 138.1(4) no . . . .
C3 C6 C14 C10 -41.6(5) no . . . .
C8 C6 C14 O1 -38.9(6) no . . . .
C8 C6 C14 C10 141.3(3) no . . . .
C14 C6 C8 C2 177.2(3) no . . . .
Cl1 C10 C14 O1 118.9(3) no . . . .
Cl1 C10 C14 C6 -61.4(4) no . . . .
C5 C10 C14 O1 -1.5(5) no . . . .
C5 C10 C14 C6 178.3(3) no . . . .
