#------------------------------------------------------------------------------
#$Date: 2025-08-21 02:19:08 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301842 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/90/4509015.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_4509015
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 &amp; 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           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 90.15(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.888(13)
_cell_length_b                   11.611(18)
_cell_length_c                   7.537(11)
_cell_measurement_reflns_used    771
_cell_measurement_temperature    270(2)
_cell_measurement_theta_max      25.21
_cell_measurement_theta_min      2.50
_cell_volume                     690.3(19)
_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      270(2)
_diffrn_measured_fraction_theta_full 0.702
_diffrn_measured_fraction_theta_max 0.702
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area detector'
_diffrn_measurement_method       'omega scan'
_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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            1803
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylindric
_exptl_crystal_F_000             288
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.108
_refine_diff_density_rms         0.025
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         953
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0439
_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/[\s^2^(Fo^2^)+(0.0300P)^2^+0.2000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                742
_reflns_number_total             953
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            cg800659fsup1.cif
_cod_data_source_block           mntoldis
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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        690.4(19)
_cod_original_sg_symbol_H-M      'P 2(1)/c'
_cod_database_code               4509015
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2377(5) 0.1901(2) 0.0288(13) 0.107(4) Uani 0.50 1 d PDU A 1
O2 O 0.3048(5) 0.3692(2) -0.0064(12) 0.070(2) Uani 0.50 1 d PDU A 1
O1' O 0.2587(5) 0.1900(3) -0.0256(12) 0.107(4) Uani 0.50 1 d PDU A 2
O2' O 0.2837(5) 0.3692(2) 0.0479(12) 0.104(4) Uani 0.50 1 d PDU A 2
N1 N 0.3390(2) 0.27032(14) 0.0400(3) 0.0745(10) Uani 1 1 d D . .
C1 C 0.5084(2) 0.24701(18) 0.1120(4) 0.0529(8) Uani 1 1 d D A .
C2 C 0.6161(3) 0.33696(19) 0.1467(5) 0.0541(9) Uani 1 1 d . . .
H2A H 0.5800 0.4121 0.1268 0.065 Uiso 1 1 calc R A .
C3 C 0.7768(3) 0.3172(2) 0.2104(5) 0.0585(10) Uani 1 1 d . A .
C4 C 0.8262(4) 0.2031(3) 0.2393(5) 0.0700(11) Uani 1 1 d . . .
H4A H 0.9346 0.1872 0.2814 0.084 Uiso 1 1 calc R A .
C5 C 0.7152(4) 0.1142(2) 0.2059(6) 0.0808(12) Uani 1 1 d . A .
H5A H 0.7495 0.0388 0.2268 0.097 Uiso 1 1 calc R . .
C6 C 0.5566(4) 0.1346(2) 0.1428(6) 0.0707(10) Uani 1 1 d . . .
H6A H 0.4822 0.0741 0.1208 0.085 Uiso 1 1 calc R A .
C7 C 0.8986(4) 0.4152(3) 0.2474(6) 0.0892(14) Uani 1 1 d . . .
H7A H 0.8368 0.4802 0.2920 0.134 Uiso 1 1 calc R A .
H7B H 0.9554 0.4363 0.1397 0.134 Uiso 1 1 calc R . .
H7C H 0.9808 0.3911 0.3339 0.134 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 0.073(4) 0.120(7) 0.127(10) -0.006(4) -0.027(4) -0.026(4)
O2 0.054(3) 0.085(5) 0.071(6) 0.018(3) -0.011(3) 0.017(3)
O1' 0.091(5) 0.117(7) 0.113(9) -0.018(4) -0.010(4) -0.039(4)
O2' 0.069(4) 0.103(6) 0.139(11) -0.013(4) 0.013(4) 0.025(4)
N1 0.0586(15) 0.0869(19) 0.078(3) -0.0106(18) -0.0012(15) -0.0088(13)
C1 0.0563(14) 0.0558(13) 0.047(3) -0.0059(12) 0.0035(13) 0.0035(12)
C2 0.0578(15) 0.0449(13) 0.060(3) 0.0024(14) 0.0037(14) 0.0033(10)
C3 0.0539(15) 0.0640(16) 0.057(3) 0.0084(13) 0.0041(14) 0.0018(13)
C4 0.0627(17) 0.088(2) 0.060(4) 0.0172(17) 0.0005(17) 0.0218(15)
C5 0.103(3) 0.0532(16) 0.086(4) 0.0072(16) 0.006(2) 0.0218(16)
C6 0.092(2) 0.0502(14) 0.070(3) -0.0067(15) 0.008(2) -0.0071(15)
C7 0.0614(17) 0.092(2) 0.114(4) 0.015(2) -0.0098(19) -0.0159(16)
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
O1 N1 O2' 118.7(4)
O2' N1 O1' 123.00(15)
O1 N1 O2 123.00(15)
O1' N1 O2 118.7(4)
O1 N1 C1 118.50(13)
O2' N1 C1 118.52(10)
O1' N1 C1 118.49(12)
O2 N1 C1 118.49(10)
C2 C1 C6 121.2(2)
C2 C1 N1 119.59(18)
C6 C1 N1 119.20(19)
C1 C2 C3 120.7(2)
C1 C2 H2A 119.7
C3 C2 H2A 119.7
C2 C3 C4 118.0(2)
C2 C3 C7 121.5(3)
C4 C3 C7 120.4(3)
C5 C4 C3 120.4(3)
C5 C4 H4A 119.8
C3 C4 H4A 119.8
C6 C5 C4 121.2(3)
C6 C5 H5A 119.4
C4 C5 H5A 119.4
C5 C6 C1 118.5(3)
C5 C6 H6A 120.7
C1 C6 H6A 120.7
C3 C7 H7A 109.5
C3 C7 H7B 109.5
H7A C7 H7B 109.5
C3 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 1.2299(17)
O2 N1 1.2302(19)
O1' N1 1.2300(16)
O2' N1 1.2300(19)
N1 C1 1.466(2)
C1 C2 1.371(3)
C1 C6 1.379(4)
C2 C3 1.374(4)
C2 H2A 0.9300
C3 C4 1.397(4)
C3 C7 1.515(4)
C4 C5 1.377(4)
C4 H4A 0.9300
C5 C6 1.358(5)
C5 H5A 0.9300
C6 H6A 0.9300
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 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
O1 N1 C1 C2 -171.8(6)
O2' N1 C1 C2 -15.5(6)
O1' N1 C1 C2 164.5(6)
O2 N1 C1 C2 8.2(6)
O1 N1 C1 C6 8.5(6)
O2' N1 C1 C6 164.8(6)
O1' N1 C1 C6 -15.2(6)
O2 N1 C1 C6 -171.5(6)
C6 C1 C2 C3 1.1(5)
N1 C1 C2 C3 -178.5(3)
C1 C2 C3 C4 -0.3(5)
C1 C2 C3 C7 179.2(3)
C2 C3 C4 C5 -0.6(5)
C7 C3 C4 C5 179.9(3)
C3 C4 C5 C6 0.6(5)
C4 C5 C6 C1 0.2(5)
C2 C1 C6 C5 -1.1(5)
N1 C1 C6 C5 178.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 7422
