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#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/13/7151386.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_7151386
loop_
_publ_author_name
'Hibbs, David E.'
'Overgaard, Jacob'
'Piltz, Ross O.'
_publ_section_title
;
 X--N Charge density analysis of the hydrogen bonding motif in
 1-(2-hydroxy-5-nitrophenyl)ethanoneElectronic supplementary
 information (ESI) available: multipole population coefficients and
 pseudoatom parameterization. See
 http://www.rsc.org/suppdata/ob/b2/b211683a/
;
_journal_issue                   7
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              1191
_journal_paper_doi               10.1039/b211683a
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C8 H7 N O4'
_chemical_formula_weight         181.15
_chemical_name_common            1-(2-hydroxy-5-nitrophenyl)ethanone
_chemical_name_systematic
;
1-(2-hydroxy-5-nitrophenyl)ethanone
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   15.1929(6)
_cell_length_b                   7.2142(3)
_cell_length_c                   7.2588(3)
_cell_measurement_reflns_used    2916
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      47.29
_cell_measurement_theta_min      4.66
_cell_volume                     795.60(6)
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.796
_diffrn_measured_fraction_theta_max 0.796
_diffrn_measurement_device_type  4-circle
_diffrn_radiation_probe          neutron
_diffrn_radiation_source         HIFAR
_diffrn_radiation_type           Neutron
_diffrn_radiation_wavelength     1.235
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2916
_diffrn_reflns_theta_full        47.29
_diffrn_reflns_theta_max         47.29
_diffrn_reflns_theta_min         4.66
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   analytical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       block
_exptl_crystal_F_000             238
_exptl_crystal_size_max          4.0
_exptl_crystal_size_mid          2.5
_exptl_crystal_size_min          1.5
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_extinction_coef       0.0507(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         671
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0226
_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)+(0.0313P)²+0.0799P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0548
_refine_ls_wR_factor_ref         0.0554
_reflns_number_gt                657
_reflns_number_total             671
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b211683a.txt
_cod_data_source_block           flav1_neutron
_cod_original_sg_symbol_H-M      'P c a 2(1)'
_cod_database_code               7151386
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,1/2+Z
3 1/2-X,+Y,1/2+Z
4 1/2+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
C1 C 0.23392(12) 0.1649(2) 0.1434(3) 0.0087(4) Uani 1 1 d . . .
C2 C 0.32472(12) 0.1266(3) 0.1153(3) 0.0081(5) Uani 1 1 d . . .
C3 C 0.38670(13) 0.2604(3) 0.1649(3) 0.0088(5) Uani 1 1 d . . .
C4 C 0.35917(13) 0.4251(3) 0.2423(3) 0.0087(5) Uani 1 1 d . . .
C5 C 0.26963(13) 0.4670(3) 0.2672(3) 0.0104(5) Uani 1 1 d . . .
C6 C 0.20764(12) 0.3368(3) 0.2158(3) 0.0104(5) Uani 1 1 d . . .
C7 C 0.35171(14) -0.0511(3) 0.0323(3) 0.0108(5) Uani 1 1 d . . .
C8 C 0.44686(15) -0.0864(3) -0.0122(4) 0.0148(6) Uani 1 1 d . . .
N1 N 0.42463(10) 0.55989(19) 0.3015(3) 0.0133(4) Uani 1 1 d . . .
O1 O 0.17083(17) 0.0450(4) 0.1000(4) 0.0135(6) Uani 1 1 d . . .
O2 O 0.29557(17) -0.1699(3) -0.0022(4) 0.0164(7) Uani 1 1 d . . .
O3 O 0.40031(16) 0.7012(3) 0.3814(4) 0.0179(6) Uani 1 1 d . . .
O4 O 0.50242(18) 0.5257(4) 0.2711(5) 0.0219(7) Uani 1 1 d . . .
H1 H 0.2000(3) -0.0694(7) 0.0519(8) 0.0257(11) Uani 1 1 d . . .
H3 H 0.4572(3) 0.2370(6) 0.1434(8) 0.0228(10) Uani 1 1 d . . .
H5 H 0.2495(3) 0.5988(6) 0.3268(8) 0.0275(11) Uani 1 1 d . . .
H6 H 0.1382(3) 0.3639(7) 0.2347(8) 0.0270(12) Uani 1 1 d . . .
H8A H 0.4526(3) -0.2181(7) -0.0831(9) 0.0416(14) Uani 1 1 d . . .
H8B H 0.4856(3) -0.0934(8) 0.1124(9) 0.0400(14) Uani 1 1 d . . .
H8C H 0.4740(3) 0.0244(7) -0.0959(10) 0.0420(15) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 117.3(2) . . ?
O1 C1 C2 122.6(2) . . ?
C6 C1 C2 120.08(17) . . ?
C3 C2 C1 118.89(18) . . ?
C3 C2 C7 121.27(17) . . ?
C1 C2 C7 119.83(17) . . ?
C4 C3 C2 119.75(19) . . ?
C3 C4 C5 122.09(19) . . ?
C3 C4 N1 119.24(17) . . ?
C5 C4 N1 118.67(18) . . ?
C6 C5 C4 118.63(19) . . ?
C5 C6 C1 120.49(18) . . ?
O2 C7 C2 119.6(2) . . ?
O2 C7 C8 120.2(2) . . ?
C2 C7 C8 120.16(18) . . ?
O4 N1 O3 122.7(2) . . ?
O4 N1 C4 118.06(19) . . ?
O3 N1 C4 119.19(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.329(3) . ?
C1 C6 1.405(3) . ?
C1 C2 1.422(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.475(3) . ?
C3 C4 1.379(3) . ?
C4 C5 1.405(3) . ?
C4 N1 1.456(3) . ?
C5 C6 1.381(3) . ?
C7 O2 1.235(3) . ?
C7 C8 1.503(3) . ?
N1 O4 1.227(3) . ?
N1 O3 1.230(3) . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -180.0(2) . . . . ?
C6 C1 C2 C3 1.5(3) . . . . ?
O1 C1 C2 C7 1.0(4) . . . . ?
C6 C1 C2 C7 -177.5(2) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C7 C2 C3 C4 -180.0(2) . . . . ?
C2 C3 C4 C5 -2.5(3) . . . . ?
C2 C3 C4 N1 177.1(2) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
N1 C4 C5 C6 -178.2(2) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
O1 C1 C6 C5 178.8(2) . . . . ?
C2 C1 C6 C5 -2.6(3) . . . . ?
C3 C2 C7 O2 176.7(3) . . . . ?
C1 C2 C7 O2 -4.3(4) . . . . ?
C3 C2 C7 C8 -4.0(4) . . . . ?
C1 C2 C7 C8 174.9(2) . . . . ?
C3 C4 N1 O4 3.8(3) . . . . ?
C5 C4 N1 O4 -176.6(2) . . . . ?
C3 C4 N1 O3 -175.3(2) . . . . ?
C5 C4 N1 O3 4.3(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 217196
