#------------------------------------------------------------------------------
#$Date: 2019-11-24 14:29:35 +0100 (dom 24 de nov de 2019) $
#$Revision: 238348 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/51/1555149.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_1555149
loop_
_publ_author_name
'Salahifar, Eslam'
'Nematollahi, Davood'
'Bayat, Mehdi'
'Mahyari, Amir'
'Amiri Rudbari, Hadi'
_publ_section_title
;
 Regioselective Green Electrochemical Approach to the Synthesis of
 Nitroacetaminophen Derivatives.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4666
_journal_page_last               4669
_journal_paper_doi               10.1021/acs.orglett.5b01837
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C8 H8 N2 O4'
_chemical_formula_weight         196.16
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8880(10)
_cell_length_b                   9.800(2)
_cell_length_c                   18.388(4)
_cell_measurement_temperature    298(2)
_cell_volume                     880.8(3)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2005)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2005)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Stoe IPDS-II'
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6890
_diffrn_reflns_theta_full        29.17
_diffrn_reflns_theta_max         29.17
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.808
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.808
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0290
_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)+(0.0339P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0558
_refine_ls_wR_factor_ref         0.0600
_reflns_number_gt                1548
_reflns_number_total             2369
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol5b01837_si_002.cif
_cod_data_source_block           o+p21212
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P2(1)2(1)2(1) '
_cod_database_code               1555149
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
O2 O 0.98525(19) 0.21736(10) 0.95695(5) 0.0532(3) Uani 1 1 d .
O3 O 0.6848(2) 0.31192(10) 0.88797(5) 0.0570(3) Uani 1 1 d .
N2 N 0.1256(2) -0.06871(11) 0.78260(6) 0.0435(3) Uani 1 1 d .
O4 O 0.0502(2) 0.14936(9) 0.74736(5) 0.0595(3) Uani 1 1 d .
O1 O 0.9132(2) -0.03218(12) 1.00170(6) 0.0595(3) Uani 1 1 d .
C6 C 0.4531(3) 0.07266(12) 0.85116(7) 0.0377(3) Uani 1 1 d .
H6 H 0.4069 0.1500 0.8246 0.045 Uiso 1 1 calc R
C5 C 0.3256(3) -0.04941(13) 0.83735(6) 0.0392(3) Uani 1 1 d .
N1 N 0.7810(2) 0.21117(11) 0.91714(5) 0.0408(3) Uani 1 1 d .
C1 C 0.6529(3) 0.08002(13) 0.90551(7) 0.0373(3) Uani 1 1 d .
C4 C 0.3980(3) -0.16280(14) 0.87927(8) 0.0511(4) Uani 1 1 d .
H4 H 0.3121 -0.2459 0.8707 0.061 Uiso 1 1 calc R
C7 C 0.0018(3) 0.02724(13) 0.74124(7) 0.0428(3) Uani 1 1 d .
C3 C 0.5923(3) -0.15416(15) 0.93258(8) 0.0534(4) Uani 1 1 d .
H3 H 0.6353 -0.2315 0.9596 0.064 Uiso 1 1 calc R
C2 C 0.7265(3) -0.03256(14) 0.94728(7) 0.0434(3) Uani 1 1 d .
C8 C -0.2019(3) -0.02609(15) 0.68736(8) 0.0536(4) Uani 1 1 d .
H8A H -0.3726 0.0210 0.6934 0.080 Uiso 1 1 calc R
H8B H -0.2289 -0.1220 0.6952 0.080 Uiso 1 1 calc R
H8C H -0.1346 -0.0114 0.6389 0.080 Uiso 1 1 calc R
H2 H 0.068(3) -0.1580(15) 0.7735(7) 0.056(4) Uiso 1 1 d .
H1 H 0.991(4) 0.051(2) 1.0054(9) 0.090(6) Uiso 1 1 d .
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
O2 0.0465(5) 0.0550(6) 0.0582(5) -0.0025(5) -0.0127(5) -0.0057(5)
O3 0.0630(6) 0.0363(5) 0.0718(6) 0.0068(5) -0.0159(5) -0.0038(5)
N2 0.0500(6) 0.0295(6) 0.0511(7) -0.0044(5) -0.0082(5) -0.0027(5)
O4 0.0702(6) 0.0321(4) 0.0760(7) 0.0002(5) -0.0270(6) -0.0017(5)
O1 0.0699(7) 0.0505(6) 0.0580(6) 0.0066(5) -0.0221(5) 0.0004(6)
C6 0.0425(7) 0.0302(6) 0.0405(6) 0.0009(5) 0.0005(6) 0.0029(6)
C5 0.0414(7) 0.0343(7) 0.0418(6) -0.0020(5) -0.0005(6) 0.0001(6)
N1 0.0404(6) 0.0398(6) 0.0421(6) -0.0026(5) -0.0004(5) -0.0016(5)
C1 0.0395(7) 0.0332(6) 0.0391(6) -0.0034(5) 0.0039(5) -0.0001(5)
C4 0.0618(9) 0.0319(7) 0.0595(8) 0.0023(7) -0.0052(8) -0.0049(7)
C7 0.0446(7) 0.0354(6) 0.0485(7) -0.0041(6) -0.0021(6) 0.0015(6)
C3 0.0665(9) 0.0382(7) 0.0555(8) 0.0095(7) -0.0077(7) -0.0001(7)
C2 0.0477(7) 0.0418(7) 0.0407(7) 0.0032(6) -0.0020(6) 0.0032(6)
C8 0.0544(9) 0.0461(8) 0.0604(8) -0.0060(7) -0.0139(7) 0.0006(7)
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 N2 C5 128.01(11)
C7 N2 H2 114.5(9)
C5 N2 H2 117.4(8)
C2 O1 H1 109.8(12)
C5 C6 C1 119.60(11)
C5 C6 H6 120.2
C1 C6 H6 120.2
C6 C5 C4 118.42(12)
C6 C5 N2 124.15(11)
C4 C5 N2 117.43(11)
O3 N1 O2 122.11(11)
O3 N1 C1 119.22(10)
O2 N1 C1 118.67(11)
C2 C1 C6 122.25(12)
C2 C1 N1 120.76(11)
C6 C1 N1 116.99(11)
C3 C4 C5 121.46(13)
C3 C4 H4 119.3
C5 C4 H4 119.3
O4 C7 N2 122.77(12)
O4 C7 C8 121.98(12)
N2 C7 C8 115.25(11)
C4 C3 C2 121.42(13)
C4 C3 H3 119.3
C2 C3 H3 119.3
O1 C2 C3 117.71(13)
O1 C2 C1 125.43(13)
C3 C2 C1 116.84(12)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 N1 1.2394(13)
O3 N1 1.2182(14)
N2 C7 1.3523(17)
N2 C5 1.4160(16)
N2 H2 0.934(15)
O4 C7 1.2251(14)
O1 C2 1.3546(16)
O1 H1 0.90(2)
C6 C5 1.3726(17)
C6 C1 1.3994(17)
C6 H6 0.9300
C5 C4 1.3979(17)
N1 C1 1.4455(16)
C1 C2 1.3915(19)
C4 C3 1.367(2)
C4 H4 0.9300
C7 C8 1.4988(18)
C3 C2 1.3869(19)
C3 H3 0.9300
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
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
C1 C6 C5 C4 0.93(18)
C1 C6 C5 N2 -178.50(11)
C7 N2 C5 C6 -8.6(2)
C7 N2 C5 C4 171.98(13)
C5 C6 C1 C2 -0.77(18)
C5 C6 C1 N1 179.59(11)
O3 N1 C1 C2 -168.82(12)
O2 N1 C1 C2 10.80(16)
O3 N1 C1 C6 10.82(15)
O2 N1 C1 C6 -169.56(11)
C6 C5 C4 C3 -0.5(2)
N2 C5 C4 C3 178.98(12)
C5 N2 C7 O4 -0.7(2)
C5 N2 C7 C8 179.76(12)
C5 C4 C3 C2 -0.2(2)
C4 C3 C2 O1 179.03(12)
C4 C3 C2 C1 0.3(2)
C6 C1 C2 O1 -178.46(12)
N1 C1 C2 O1 1.2(2)
C6 C1 C2 C3 0.13(19)
N1 C1 C2 C3 179.75(12)
