#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:46:13 +0300 (Mon, 04 May 2020) $
#$Revision: 251478 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038250.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_4038250
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_sum            'C8 H5 Cl N2 O3'
_chemical_formula_weight         212.59
_chemical_name_common            furoxan
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 92.046(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5586(13)
_cell_length_b                   7.4628(14)
_cell_length_c                   8.5758(17)
_cell_measurement_reflns_used    1212
_cell_measurement_temperature    90.(2)
_cell_measurement_theta_max      27.4883
_cell_measurement_theta_min      2.3764
_cell_volume                     419.48(14)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      90.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2452
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.38
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Turbo X-ray Source'
_exptl_absorpt_coefficient_mu    0.434
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.067
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.019
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.219
_refine_ls_abs_structure_details
;

Flack x determined using 564 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1663
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0375P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0760
_reflns_number_gt                1555
_reflns_number_total             1663
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00326_si_004.cif
_cod_data_source_block           HH121_3a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4038245--4038253.cif.
;
_cod_database_code               4038250
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.08626(10) 0.42860(10) 0.13108(8) 0.01835(18) Uani d . . . 1 . .
N N1 0.3826(4) 0.6391(4) 0.0445(3) 0.0164(5) Uani d . . . 1 . .
O O1 0.3128(4) 0.7002(3) -0.0803(3) 0.0214(5) Uani d . . . 1 . .
C C1 0.3163(4) 0.5265(4) 0.1495(3) 0.0136(6) Uani d . . . 1 . .
O O2 0.5819(4) 0.6965(3) 0.0962(3) 0.0181(5) Uani d . . . 1 . .
N N2 0.6292(4) 0.6130(3) 0.2390(3) 0.0162(5) Uani d . . . 1 . .
C C2 0.4716(4) 0.5136(4) 0.2682(3) 0.0130(6) Uani d . . . 1 . .
C C3 0.6270(4) 0.4035(4) 0.4979(3) 0.0144(6) Uani d . . . 1 . .
O O3 0.4525(3) 0.4115(3) 0.3942(2) 0.0157(4) Uani d . . . 1 . .
C C4 0.7970(5) 0.3093(4) 0.4533(4) 0.0156(6) Uani d . . . 1 . .
H H4 0.800463 0.253225 0.354027 0.019 Uiso calc U . R 1 . .
C C5 0.9629(5) 0.2994(4) 0.5590(3) 0.0163(6) Uani d . . . 1 . .
H H5 1.082769 0.237394 0.531227 0.02 Uiso calc U . R 1 . .
C C6 0.9541(5) 0.3798(4) 0.7048(3) 0.0172(7) Uani d . . . 1 . .
H H6 1.068072 0.373447 0.776143 0.021 Uiso calc U . R 1 . .
C C7 0.7790(5) 0.4690(4) 0.7461(3) 0.0177(7) Uani d . . . 1 . .
H H7 0.772941 0.522318 0.846375 0.021 Uiso calc U . R 1 . .
C C8 0.6126(5) 0.4812(4) 0.6427(3) 0.0155(7) Uani d . . . 1 . .
H H8 0.491803 0.541612 0.670952 0.019 Uiso calc U . R 1 . .
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'
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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 N1 C1 . . 134.9(3) ?
O1 N1 O2 . . 117.7(2) ?
C1 N1 O2 . . 107.4(2) ?
N1 C1 C2 . . 106.8(3) ?
N1 C1 Cl1 . . 122.1(2) ?
C2 C1 Cl1 . . 131.2(2) ?
N2 O2 N1 . . 108.0(2) ?
C2 N2 O2 . . 105.7(2) ?
N2 C2 O3 . . 125.4(3) ?
N2 C2 C1 . . 112.2(3) ?
O3 C2 C1 . . 122.4(3) ?
C8 C3 C4 . . 123.0(3) ?
C8 C3 O3 . . 117.8(3) ?
C4 C3 O3 . . 119.1(2) ?
C2 O3 C3 . . 115.7(2) ?
C3 C4 C5 . . 117.8(3) ?
C3 C4 H4 . . 121.1 ?
C5 C4 H4 . . 121.1 ?
C6 C5 C4 . . 120.4(3) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C7 C6 C5 . . 119.9(3) ?
C7 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
C8 C7 C6 . . 120.7(3) ?
C8 C7 H7 . . 119.6 ?
C6 C7 H7 . . 119.6 ?
C3 C8 C7 . . 118.1(3) ?
C3 C8 H8 . . 120.9 ?
C7 C8 H8 . . 120.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 . 1.679(3) ?
N1 O1 . 1.236(3) ?
N1 C1 . 1.317(4) ?
N1 O2 . 1.431(3) ?
C1 C2 . 1.418(4) ?
O2 N2 . 1.399(3) ?
N2 C2 . 1.304(4) ?
C2 O3 . 1.331(3) ?
C3 C8 . 1.377(4) ?
C3 C4 . 1.384(4) ?
C3 O3 . 1.425(3) ?
C4 C5 . 1.393(4) ?
C4 H4 . 0.95 ?
C5 C6 . 1.390(4) ?
C5 H5 . 0.95 ?
C6 C7 . 1.384(4) ?
C6 H6 . 0.95 ?
C7 C8 . 1.384(4) ?
C7 H7 . 0.95 ?
C8 H8 . 0.95 ?
