#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/09/7220944.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_7220944
loop_
_publ_author_name
'Takahashi, Hiroki'
'Tamura, Rui'
_publ_section_title
;
 Low temperature phase transition induced biaxial negative thermal
 expansion of 2,4-dinitroanisole
;
_journal_issue                   46
_journal_name_full               CrystEngComm
_journal_page_first              8888
_journal_paper_doi               10.1039/C5CE00029G
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C7 H6 N2 O5'
_chemical_formula_weight         198.14
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-12-26 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.164(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8537(15)
_cell_length_b                   13.804(5)
_cell_length_c                   15.381(6)
_cell_measurement_reflns_used    2183
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     813.5(5)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r4 (Rigaku/MSC, 2009)
;
_computing_molecular_graphics
;
Yadokari-XG 2009 (Kabuto, 2009), ORTEP-3 (Farrugia, 1997) & Mercury (Macrae et
al., 2006)
;
_computing_publication_material
'PLATON (Speak, 2009) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device
;
AFC11 (Right): Eulerian 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3706
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.9724
_exptl_absorpt_correction_T_min  0.9724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrystalClear (Rigaku Americas and Rigaku, 2009)'
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0404
_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)+(0.0684P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1155
_reflns_number_gt                1372
_reflns_number_total             1835
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce00029g2.cif
_cod_data_source_block           24dnan_173K
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7220936--7220954.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7220944
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 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
C1 C 0.4002(4) 0.18302(10) 0.92685(9) 0.0254(3) Uani 1 1 d
C2 C 0.4802(4) 0.25744(10) 0.98871(9) 0.0257(3) Uani 1 1 d
C3 C 0.6106(4) 0.34586(11) 0.96564(9) 0.0271(3) Uani 1 1 d
H1 H 0.657(4) 0.3939(14) 1.0081(12) 0.041(5) Uiso 1 1 d
C4 C 0.6625(4) 0.36070(10) 0.87894(9) 0.0276(3) Uani 1 1 d
C5 C 0.5913(4) 0.28956(12) 0.81616(9) 0.0304(4) Uani 1 1 d
H2 H 0.621(5) 0.3010(13) 0.7571(12) 0.040(5) Uiso 1 1 d
C6 C 0.4617(4) 0.20155(11) 0.84008(9) 0.0291(3) Uani 1 1 d
H3 H 0.414(5) 0.1539(12) 0.7942(12) 0.037(5) Uiso 1 1 d
C7 C 0.2001(5) 0.02270(12) 0.89040(11) 0.0358(4) Uani 1 1 d
H6 H 0.036(5) 0.0459(12) 0.8425(12) 0.041(5) Uiso 1 1 d
H5 H 0.109(5) -0.0294(14) 0.9215(12) 0.048(5) Uiso 1 1 d
H4 H 0.410(5) 0.0007(11) 0.8658(11) 0.034(4) Uiso 1 1 d
N1 N 0.4314(4) 0.24501(9) 1.08162(8) 0.0314(3) Uani 1 1 d
N2 N 0.8021(4) 0.45417(10) 0.85462(8) 0.0348(3) Uani 1 1 d
O1 O 0.2765(3) 0.09857(8) 0.95368(6) 0.0319(3) Uani 1 1 d
O2 O 0.2238(4) 0.18444(9) 1.10154(8) 0.0537(4) Uani 1 1 d
O3 O 0.5977(4) 0.29676(10) 1.13437(7) 0.0564(4) Uani 1 1 d
O4 O 0.8245(4) 0.51938(9) 0.90873(8) 0.0572(4) Uani 1 1 d
O5 O 0.8920(4) 0.46274(10) 0.78091(8) 0.0527(4) Uani 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
C1 0.0238(8) 0.0306(7) 0.0221(7) 0.0024(6) 0.0034(5) 0.0009(6)
C2 0.0275(8) 0.0315(8) 0.0187(7) 0.0030(6) 0.0053(5) 0.0016(6)
C3 0.0307(8) 0.0289(7) 0.0215(7) 0.0006(6) 0.0022(6) -0.0003(6)
C4 0.0259(8) 0.0326(8) 0.0246(7) 0.0068(6) 0.0042(5) 0.0005(6)
C5 0.0323(8) 0.0417(8) 0.0179(7) 0.0037(6) 0.0064(6) 0.0015(7)
C6 0.0332(8) 0.0344(8) 0.0201(7) -0.0019(6) 0.0051(6) 0.0003(6)
C7 0.0408(10) 0.0356(9) 0.0318(8) -0.0067(7) 0.0079(7) -0.0083(8)
N1 0.0451(8) 0.0295(6) 0.0205(6) 0.0010(5) 0.0076(5) 0.0004(6)
N2 0.0367(8) 0.0384(7) 0.0295(7) 0.0095(6) 0.0040(5) -0.0036(6)
O1 0.0427(7) 0.0295(5) 0.0245(5) -0.0016(4) 0.0086(4) -0.0062(5)
O2 0.0870(11) 0.0474(7) 0.0317(6) -0.0032(6) 0.0299(7) -0.0236(7)
O3 0.0823(11) 0.0658(8) 0.0198(6) -0.0022(6) -0.0007(6) -0.0270(7)
O4 0.0898(11) 0.0404(7) 0.0427(7) 0.0002(6) 0.0137(7) -0.0208(7)
O5 0.0721(10) 0.0537(8) 0.0355(7) 0.0141(6) 0.0211(6) -0.0106(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
O1 C1 C6 123.56(13)
O1 C1 C2 118.97(12)
C6 C1 C2 117.47(13)
C3 C2 C1 121.96(13)
C3 C2 N1 116.15(12)
C1 C2 N1 121.89(13)
C2 C3 C4 118.19(14)
C2 C3 H1 119.7(11)
C4 C3 H1 122.1(11)
C5 C4 C3 121.92(14)
C5 C4 N2 119.90(13)
C3 C4 N2 118.18(13)
C6 C5 C4 119.31(14)
C6 C5 H2 119.4(11)
C4 C5 H2 121.3(11)
C5 C6 C1 121.15(14)
C5 C6 H3 116.8(10)
C1 C6 H3 122.1(10)
O1 C7 H6 110.0(10)
O1 C7 H5 105.7(11)
H6 C7 H5 112.7(15)
O1 C7 H4 111.7(10)
H6 C7 H4 107.8(14)
H5 C7 H4 108.9(14)
O3 N1 O2 123.40(13)
O3 N1 C2 117.90(13)
O2 N1 C2 118.69(13)
O4 N2 O5 123.51(14)
O4 N2 C4 118.45(12)
O5 N2 C4 118.04(14)
C1 O1 C7 118.57(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.3412(18)
C1 C6 1.404(2)
C1 C2 1.412(2)
C2 C3 1.381(2)
C2 N1 1.4714(18)
C3 C4 1.385(2)
C3 H1 0.934(19)
C4 C5 1.384(2)
C4 N2 1.462(2)
C5 C6 1.378(2)
C5 H2 0.941(18)
C6 H3 0.967(17)
C7 O1 1.4384(19)
C7 H6 0.971(19)
C7 H5 0.95(2)
C7 H4 0.978(18)
N1 O3 1.2115(17)
N1 O2 1.2188(17)
N2 O4 1.2227(18)
N2 O5 1.2263(16)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H1 O4 0.934(19) 2.552(17) 3.321(2) 139.8(13) 3_767 yes
C5 H2 O2 0.941(19) 2.475(18) 3.413(2) 174.6(15) 4_554 yes
C7 H4 O5 0.978(19) 2.514(17) 3.315(3) 139.1(14) 2_646 yes
C7 H5 O2 0.952(19) 2.501(19) 3.302(3) 141.9(15) 3_557 yes
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 C1 C2 C3 179.55(13)
C6 C1 C2 C3 0.7(2)
O1 C1 C2 N1 -0.1(2)
C6 C1 C2 N1 -178.94(13)
C1 C2 C3 C4 0.1(2)
N1 C2 C3 C4 179.70(12)
C2 C3 C4 C5 -0.8(2)
C2 C3 C4 N2 -179.72(13)
C3 C4 C5 C6 0.7(2)
N2 C4 C5 C6 179.61(14)
C4 C5 C6 C1 0.1(2)
O1 C1 C6 C5 -179.59(14)
C2 C1 C6 C5 -0.8(2)
C3 C2 N1 O3 -21.8(2)
C1 C2 N1 O3 157.80(15)
C3 C2 N1 O2 157.28(14)
C1 C2 N1 O2 -23.1(2)
C5 C4 N2 O4 171.66(14)
C3 C4 N2 O4 -9.4(2)
C5 C4 N2 O5 -8.6(2)
C3 C4 N2 O5 170.33(14)
C6 C1 O1 C7 -0.4(2)
C2 C1 O1 C7 -179.19(14)
