#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:46:13 +0300 (Mon, 04 May 2020) $
#$Revision: 251478 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038246.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_4038246
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         'C12 H13 Cl N2 O3'
_chemical_formula_sum            'C12 H13 Cl N2 O3'
_chemical_formula_weight         268.70
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.3519(10)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   7.5174(6)
_cell_length_b                   10.8721(9)
_cell_length_c                   7.6231(6)
_cell_measurement_reflns_used    2942
_cell_measurement_temperature    90
_cell_measurement_theta_max      28.735
_cell_measurement_theta_min      2.712
_cell_volume                     622.51(9)
_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    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      90
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3491
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            NONE
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NONE
_exptl_crystal_F_000             280.00
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.153
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.220
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  755 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.49(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2190
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0227
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0392P)²+0.0528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0612
_reflns_number_gt                2163
_reflns_number_total             2190
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo0c00326_si_003.cif
_cod_data_source_block           AA945_HPLC1_0am
_cod_depositor_comments
'Adding full bibliography for 4038245--4038253.cif.'
_cod_database_code               4038246
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+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 0.13652(4) 0.51337(3) 0.10711(4) 0.01548(9) Uani 1.0 2 d . . .
O2 O 0.16475(14) 0.16409(11) 0.18234(14) 0.0174(3) Uani 1.0 2 d . . .
O3 O 0.47970(13) 0.38265(11) 0.30331(13) 0.0144(3) Uani 1.0 2 d . . .
O4 O -0.06816(14) 0.26659(12) 0.04458(14) 0.0216(3) Uani 1.0 2 d . . .
N6 N 0.33013(16) 0.19576(12) 0.26257(16) 0.0158(3) Uani 1.0 2 d . . .
N19 N 0.08123(17) 0.27483(13) 0.11833(15) 0.0152(3) Uani 1.0 2 d . . .
C7 C 0.92174(18) 0.33415(15) 0.5431(2) 0.0144(3) Uani 1.0 2 d . . .
C8 C 1.23354(19) 0.36191(15) 0.69360(19) 0.0128(3) Uani 1.0 2 d . . .
C9 C 1.37779(19) 0.43560(15) 0.74839(19) 0.0155(3) Uani 1.0 2 d . . .
C10 C 0.18961(18) 0.36667(13) 0.15760(18) 0.0122(3) Uani 1.0 2 d . . .
C11 C 1.53333(19) 0.26042(16) 0.87332(18) 0.0168(3) Uani 1.0 2 d . . .
C12 C 0.34250(19) 0.31523(14) 0.24618(18) 0.0129(3) Uani 1.0 2 d . . .
C13 C 1.5253(2) 0.38635(16) 0.83799(19) 0.0169(3) Uani 1.0 2 d . . .
C14 C 0.62442(18) 0.31267(15) 0.38952(19) 0.0149(3) Uani 1.0 2 d . . .
C15 C 1.07157(19) 0.42096(14) 0.60237(19) 0.0146(3) Uani 1.0 2 d . . .
C16 C 1.24435(19) 0.23547(14) 0.72778(18) 0.0142(3) Uani 1.0 2 d . . .
C17 C 1.39360(19) 0.18566(15) 0.81650(18) 0.0170(3) Uani 1.0 2 d . . .
C18 C 0.76973(19) 0.40155(15) 0.44450(19) 0.0148(3) Uani 1.0 2 d . . .
H7A H 0.8757 0.2935 0.6451 0.0172 Uiso 1.0 2 calc R . .
H7B H 0.9689 0.2714 0.4674 0.0172 Uiso 1.0 2 calc R . .
H9 H 1.3747 0.5194 0.7242 0.0186 Uiso 1.0 2 calc R . .
H11 H 1.6316 0.2271 0.9344 0.0201 Uiso 1.0 2 calc R . .
H13 H 1.6191 0.4372 0.8746 0.0203 Uiso 1.0 2 calc R . .
H14A H 0.6695 0.2520 0.3093 0.0178 Uiso 1.0 2 calc R . .
H14B H 0.5817 0.2701 0.4914 0.0178 Uiso 1.0 2 calc R . .
H15A H 1.1106 0.4650 0.5002 0.0175 Uiso 1.0 2 calc R . .
H15B H 1.0235 0.4812 0.6815 0.0175 Uiso 1.0 2 calc R . .
H16 H 1.1511 0.1842 0.6910 0.0170 Uiso 1.0 2 calc R . .
H17 H 1.3992 0.1015 0.8376 0.0203 Uiso 1.0 2 calc R . .
H18A H 0.7220 0.4645 0.5196 0.0178 Uiso 1.0 2 calc R . .
H18B H 0.8146 0.4415 0.3415 0.0178 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
N6 O2 N19 108.03(11) yes . . .
C12 O3 C14 114.52(13) yes . . .
O2 N6 C12 105.47(12) yes . . .
O2 N19 O4 118.03(13) yes . . .
O2 N19 C10 107.54(12) yes . . .
O4 N19 C10 134.42(15) yes . . .
C15 C7 C18 112.17(13) yes . . .
C9 C8 C15 119.45(14) yes . . .
C9 C8 C16 117.93(14) yes . . .
C15 C8 C16 122.62(13) yes . . .
C8 C9 C13 121.40(15) yes . . .
Cl1 C10 N19 121.86(11) yes . . .
Cl1 C10 C12 131.26(12) yes . . .
N19 C10 C12 106.87(13) yes . . .
C13 C11 C17 119.31(14) yes . . .
O3 C12 N6 125.13(13) yes . . .
O3 C12 C10 122.77(14) yes . . .
N6 C12 C10 112.09(13) yes . . .
C9 C13 C11 120.08(15) yes . . .
O3 C14 C18 108.02(13) yes . . .
C7 C15 C8 116.27(13) yes . . .
C8 C16 C17 120.68(14) yes . . .
C11 C17 C16 120.58(15) yes . . .
C7 C18 C14 110.40(13) yes . . .
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 1.6848(15) yes . .
O2 N6 1.4056(16) yes . .
O2 N19 1.4341(18) yes . .
O3 C12 1.3243(18) yes . .
O3 C14 1.4614(18) yes . .
O4 N19 1.2383(17) yes . .
N6 C12 1.309(2) yes . .
N19 C10 1.315(2) yes . .
C7 C15 1.524(2) yes . .
C7 C18 1.529(2) yes . .
C8 C9 1.398(2) yes . .
C8 C15 1.519(2) yes . .
C8 C16 1.401(3) yes . .
C9 C13 1.386(2) yes . .
C10 C12 1.423(2) yes . .
C11 C13 1.396(3) yes . .
C11 C17 1.384(3) yes . .
C14 C18 1.505(2) yes . .
C16 C17 1.395(2) yes . .
