#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:16:50 +0200 (vie 13 de oct de 2017) $
#$Revision: 201980 $
#$URL: svn://www.crystallography.net/cod/cif/2/30/03/2300303.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_2300303
loop_
_publ_author_name
'Probert, Michael R.'
'Robertson, Craig M.'
'Coome, Jonathan A.'
'Howard, Judith A. K.'
'Michell, Brian C.'
'Goeta, Andrés E.'
_publ_section_title
;
 The XIPHOS diffraction facility for extreme sample conditions
;
_journal_coeditor_code           HX5107
_journal_issue                   6
_journal_name_full               'Journal of Applied Crystallography'
_journal_page_first              1415
_journal_page_last               1418
_journal_paper_doi               10.1107/S0021889810041282
_journal_volume                  43
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C6 H6 N2 O2'
_chemical_formula_sum            'C6 H6 N2 O2'
_chemical_formula_weight         138.13
_chemical_name_systematic        m-nitroaniline
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_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
_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                   18.7169(4)
_cell_length_b                   6.5215(2)
_cell_length_c                   5.00140(10)
_cell_measurement_reflns_used    3128
_cell_measurement_temperature    2.0
_cell_measurement_theta_max      30.407
_cell_measurement_theta_min      3.308
_cell_volume                     610.48(3)
_computing_cell_refinement       'Bruker SAINT version 7.68a (Bruker, 2010)'
_computing_data_collection       'Bruker APEXII v2010.1-2 (Bruker, 2010)'
_computing_data_reduction        'Bruker SAINT version 7.68a (Bruker, 2010)'
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program. 
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program. 
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution
;
A short history of SHELX (Sheldrick, 2007)/Bruker
;
_diffrn_ambient_temperature      2.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEXII area detector'
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'XIPHOS four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    focused
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Bruker TXS with Helios Optics'
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9614
_diffrn_reflns_theta_full        30.41
_diffrn_reflns_theta_max         30.41
_diffrn_reflns_theta_min         2.18
_diffrn_source                   'rotating anode'
_diffrn_source_target            Mo
_diffrn_source_type              'Bruker TXS with Helios Optics'
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.6107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2008/1 (Bruker,2008) was used for absorption correction.
 R(int) was 0.0670 before and 0.0419 after correction.
 The Ratio of minimum to maximum transmission is 0.818632707775.
 The λ/2 correction factor is Not present
;
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_preparation       'crystal was mounted on a graphite fibre'
_exptl_crystal_recrystallization_method 'slow evaporation from EtOH'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'not refined as all light atom structure'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         993
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0327
_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)+(0.0542P)²+0.2014P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                935
_reflns_number_total             993
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            hx5107.cif
_cod_data_source_block           mna_2_K
_cod_database_code               2300303
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'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
O1 O 0.39879(6) 1.06784(19) 0.0795(3) 0.0132(3) Uani 1 1 d . . .
O2 O 0.30390(6) 0.89456(19) -0.0261(3) 0.0124(3) Uani 1 1 d . . .
N1 N 0.30431(7) 0.2819(2) 0.5743(3) 0.0106(3) Uani 1 1 d . . .
N2 N 0.35802(7) 0.9202(2) 0.1096(3) 0.0092(3) Uani 1 1 d . . .
C5 C 0.37561(8) 0.7694(2) 0.3170(3) 0.0084(3) Uani 1 1 d . . .
C6 C 0.33173(9) 0.5977(2) 0.3415(3) 0.0092(3) Uani 1 1 d . . .
C1 C 0.34867(8) 0.4516(2) 0.5354(3) 0.0089(3) Uani 1 1 d . . .
C2 C 0.40898(8) 0.4832(3) 0.6982(3) 0.0101(3) Uani 1 1 d . . .
C3 C 0.45130(8) 0.6569(3) 0.6668(3) 0.0102(3) Uani 1 1 d . . .
C4 C 0.43576(8) 0.8043(3) 0.4746(4) 0.0097(3) Uani 1 1 d . . .
H6 H 0.2909(12) 0.582(4) 0.229(6) 0.015(6) Uiso 1 1 d . . .
H4 H 0.4634(12) 0.926(4) 0.460(7) 0.018(6) Uiso 1 1 d . . .
H2 H 0.4188(14) 0.387(4) 0.827(7) 0.020(6) Uiso 1 1 d . . .
H1A H 0.2771(11) 0.259(3) 0.448(6) 0.009(5) Uiso 1 1 d . . .
H3 H 0.4923(12) 0.677(3) 0.779(5) 0.011(6) Uiso 1 1 d . . .
H1B H 0.3231(12) 0.176(4) 0.657(6) 0.015(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
O1 0.0141(6) 0.0090(5) 0.0164(6) 0.0024(5) -0.0003(5) -0.0029(4)
O2 0.0119(5) 0.0120(6) 0.0133(6) 0.0018(5) -0.0029(5) 0.0000(4)
N1 0.0108(6) 0.0089(6) 0.0121(6) 0.0019(6) -0.0018(6) -0.0017(5)
N2 0.0099(6) 0.0078(6) 0.0097(6) 0.0000(5) 0.0007(6) 0.0010(4)
C5 0.0098(7) 0.0068(7) 0.0086(6) 0.0010(6) -0.0002(6) 0.0019(5)
C6 0.0093(7) 0.0081(7) 0.0101(6) -0.0014(6) 0.0004(6) -0.0002(5)
C1 0.0093(6) 0.0081(7) 0.0094(7) -0.0003(6) 0.0025(5) 0.0011(5)
C2 0.0104(7) 0.0093(7) 0.0104(7) 0.0019(6) 0.0007(6) 0.0005(6)
C3 0.0090(6) 0.0109(7) 0.0109(7) 0.0003(6) -0.0012(6) 0.0000(5)
C4 0.0104(6) 0.0076(6) 0.0111(7) 0.0001(6) 0.0004(6) -0.0015(5)
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 0.0000 '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 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 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 N2 C5 117.99(13) . . ?
O2 N2 O1 123.07(14) . . ?
O2 N2 C5 118.94(13) . . ?
N1 C1 C2 120.82(15) . . ?
C5 C6 C1 118.41(15) . . ?
C5 C6 H6 120.4(16) . . ?
C5 C4 H4 122.2(18) . . ?
C6 C5 N2 117.94(14) . . ?
C6 C1 N1 120.18(14) . . ?
C6 C1 C2 118.94(15) . . ?
C1 N1 H1A 113.7(16) . . ?
C1 N1 H1B 116.8(15) . . ?
C1 C6 H6 121.2(16) . . ?
C1 C2 H2 117.7(17) . . ?
C2 C3 H3 119.9(14) . . ?
C3 C2 C1 120.73(15) . . ?
C3 C2 H2 121.5(17) . . ?
C3 C4 C5 116.59(14) . . ?
C3 C4 H4 121.1(18) . . ?
C4 C5 N2 118.18(14) . . ?
C4 C5 C6 123.88(15) . . ?
C4 C3 C2 121.46(15) . . ?
C4 C3 H3 118.7(14) . . ?
H1A N1 H1B 118(2) . . ?
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
O1 N2 1.2379(17) . ?
O2 N2 1.2307(18) . ?
N1 C1 1.397(2) . ?
N1 H1A 0.83(3) . ?
N1 H1B 0.88(3) . ?
N2 C5 1.466(2) . ?
C5 C6 1.394(2) . ?
C5 C4 1.393(2) . ?
C6 C1 1.396(2) . ?
C6 H6 0.96(3) . ?
C1 C2 1.407(2) . ?
C2 C3 1.391(2) . ?
C2 H2 0.92(3) . ?
C3 C4 1.390(2) . ?
C3 H3 0.96(2) . ?
C4 H4 0.95(2) . ?
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 N2 C5 C6 -176.72(14) . . . . ?
O1 N2 C5 C4 2.2(2) . . . . ?
O2 N2 C5 C6 3.2(2) . . . . ?
O2 N2 C5 C4 -177.92(15) . . . . ?
N1 C1 C2 C3 -177.16(15) . . . . ?
N2 C5 C6 C1 178.97(15) . . . . ?
N2 C5 C4 C3 -179.20(15) . . . . ?
C5 C6 C1 N1 177.17(14) . . . . ?
C5 C6 C1 C2 0.1(2) . . . . ?
C6 C5 C4 C3 -0.3(2) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7145
