#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/90/4509013.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4509013
loop_
_publ_author_name
'Yakovenko, Andrey A.'
'Antipin, Mikhail Yu.'
'Timofeeva, Tatiana V.'
_publ_section_title
;
 Molecular and Crystal Structure of Low Melting Nitrotoluene Isomers
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              57
_journal_paper_doi               10.1021/cg800659f
_journal_volume                  9
_journal_year                    2009
_chemical_formula_moiety         'C7 H7 N O2'
_chemical_formula_sum            'C7 H7 N O2'
_chemical_formula_weight         137.14
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   13.6516(19)
_cell_length_b                   6.3323(9)
_cell_length_c                   15.573(2)
_cell_measurement_reflns_used    3206
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.67
_cell_measurement_theta_min      2.61
_cell_volume                     1346.2(3)
_computing_cell_refinement       'SAINT+ ver. 6.2 (Bruker, 2001)'
_computing_data_collection       'APEX2  (Bruker, 2005)'
_computing_data_reduction        'SAINT+ ver. 6.2 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_computing_structure_solution    'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0231
_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       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17417
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9800
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0438
_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)+(0.0300P)²+0.9000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.1010
_reflns_number_gt                1413
_reflns_number_total             1768
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg800659fsup1.cif
_cod_data_source_block           nittol
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1346.3(3)
_cod_original_sg_symbol_Hall     '-P 2ac 2ab '
_cod_database_code               4509013
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
O1 O 0.92277(8) 0.42393(16) 0.39850(7) 0.0337(3) Uani 1 1 d .
N1 N 0.89251(9) 0.24114(18) 0.39444(7) 0.0236(3) Uani 1 1 d .
C1 C 0.88429(9) 0.1189(2) 0.47428(8) 0.0199(3) Uani 1 1 d .
O2 O 0.86872(9) 0.15581(18) 0.32682(7) 0.0378(3) Uani 1 1 d .
C2 C 0.84849(10) -0.0858(2) 0.47035(9) 0.0212(3) Uani 1 1 d .
H2 H 0.8293(12) -0.146(3) 0.4160(11) 0.036(5) Uiso 1 1 d .
C3 C 0.83993(10) -0.1985(2) 0.54659(9) 0.0225(3) Uani 1 1 d .
H3 H 0.8143(11) -0.338(3) 0.5444(10) 0.026(4) Uiso 1 1 d .
C4 C 0.86661(10) -0.1090(2) 0.62538(8) 0.0233(3) Uani 1 1 d .
C5 C 0.90279(10) 0.0984(2) 0.62630(9) 0.0233(3) Uani 1 1 d .
H5 H 0.9215(12) 0.162(3) 0.6795(11) 0.033(4) Uiso 1 1 d .
C6 C 0.91232(10) 0.2133(2) 0.55094(9) 0.0217(3) Uani 1 1 d .
H6 H 0.9371(12) 0.351(3) 0.5527(10) 0.026(4) Uiso 1 1 d .
C7 C 0.85728(12) -0.2341(2) 0.70726(9) 0.0322(3) Uani 1 1 d .
H7A H 0.8939 -0.3666 0.7018 0.048 Uiso 1 1 calc R
H7B H 0.7881 -0.2655 0.7181 0.048 Uiso 1 1 calc R
H7C H 0.8838 -0.1518 0.7552 0.048 Uiso 1 1 calc R
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 0.0456(7) 0.0197(5) 0.0358(6) 0.0063(4) -0.0040(5) -0.0064(4)
N1 0.0273(6) 0.0206(5) 0.0230(5) 0.0017(4) -0.0008(4) 0.0010(4)
C1 0.0217(6) 0.0182(6) 0.0198(6) 0.0008(5) 0.0006(5) 0.0029(5)
O2 0.0613(8) 0.0309(6) 0.0212(5) 0.0006(4) -0.0058(5) -0.0063(5)
C2 0.0231(6) 0.0188(6) 0.0218(6) -0.0035(5) -0.0010(5) 0.0005(5)
C3 0.0231(6) 0.0175(6) 0.0269(7) -0.0003(5) -0.0001(5) 0.0004(5)
C4 0.0219(6) 0.0239(6) 0.0240(6) 0.0012(5) 0.0007(5) 0.0018(5)
C5 0.0244(6) 0.0244(6) 0.0212(6) -0.0037(5) -0.0017(5) 0.0007(5)
C6 0.0229(6) 0.0167(6) 0.0256(6) -0.0025(5) -0.0010(5) -0.0003(5)
C7 0.0371(8) 0.0333(8) 0.0261(7) 0.0072(6) 0.0008(6) -0.0021(6)
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
O2 N1 O1 123.16(12)
O2 N1 C1 118.30(11)
O1 N1 C1 118.54(11)
C6 C1 C2 122.50(12)
C6 C1 N1 118.67(11)
C2 C1 N1 118.83(12)
C3 C2 C1 118.15(12)
C3 C2 H2 121.4(11)
C1 C2 H2 120.4(11)
C2 C3 C4 121.26(12)
C2 C3 H3 118.5(9)
C4 C3 H3 120.2(9)
C3 C4 C5 118.66(12)
C3 C4 C7 120.45(13)
C5 C4 C7 120.89(12)
C6 C5 C4 121.02(12)
C6 C5 H5 119.2(11)
C4 C5 H5 119.7(11)
C1 C6 C5 118.40(12)
C1 C6 H6 121.7(10)
C5 C6 H6 119.9(10)
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.2306(15)
N1 O2 1.2274(15)
N1 C1 1.4688(16)
C1 C6 1.3889(18)
C1 C2 1.3869(18)
C2 C3 1.3901(19)
C2 H2 0.965(18)
C3 C4 1.3998(19)
C3 H3 0.952(17)
C4 C5 1.4027(19)
C4 C7 1.5069(19)
C5 C6 1.3873(19)
C5 H5 0.956(17)
C6 H6 0.933(17)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
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
O2 N1 C1 C6 179.14(12)
O1 N1 C1 C6 -0.92(18)
O2 N1 C1 C2 -1.14(19)
O1 N1 C1 C2 178.80(12)
C6 C1 C2 C3 0.6(2)
N1 C1 C2 C3 -179.16(11)
C1 C2 C3 C4 -0.1(2)
C2 C3 C4 C5 -0.2(2)
C2 C3 C4 C7 -179.67(13)
C3 C4 C5 C6 -0.1(2)
C7 C4 C5 C6 179.40(13)
C2 C1 C6 C5 -0.82(19)
N1 C1 C6 C5 178.90(12)
C4 C5 C6 C1 0.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 7473
