#------------------------------------------------------------------------------
#$Date: 2015-11-29 03:30:11 +0200 (Sun, 29 Nov 2015) $
#$Revision: 170589 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/03/2020303.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2020303
loop_
_publ_author_name
'Bustos, Carlos'
'Alvarez-Thon, Luis'
'Baggio, Ricardo'
_publ_section_title
;
 Structural aspects of two α-dihydrazones displaying a complete survey of
 intermolecular interactions
;
_journal_coeditor_code           FP3020
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229615021944
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C15 H14 N6 O4'
_chemical_formula_moiety         'C15 H14 N6 O4'
_chemical_formula_sum            'C15 H14 N6 O4'
_chemical_formula_weight         342.32
_chemical_name_systematic
(2'E,2'E)-2,2'-(Propane-1,2-diylidene)bis[1-(2-nitrophenyl)hydrazine]
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90.05(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9382(16)
_cell_length_b                   7.3484(15)
_cell_length_c                   25.847(5)
_cell_measurement_reflns_used    2932
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.83
_cell_measurement_theta_min      2.87
_cell_volume                     1507.7(5)
_computing_cell_refinement
;
SAINT (Bruker, 2002)
;
_computing_data_collection
;
SMART (Bruker, 2001)
;
_computing_data_reduction
;
SAINT (Bruker, 2002)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and
Mercury (Macrae et al.,  2006)
;
_computing_structure_refinement
;
SHELXL2014 Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12121
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.873
_diffrn_reflns_theta_min         1.576
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS in SAINT-NT; Bruker, 2002)
;
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       Polyhedron
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.866
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3365
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.866
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0516P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0917
_reflns_number_gt                2175
_reflns_number_total             3365
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fp3020sup1.cif
_cod_data_source_block           I
_cod_database_code               2020303
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
O O1 0.30892(12) 0.20393(13) 0.26910(4) 0.0347(3) Uani d 1
O O2 0.49328(15) 0.41876(16) 0.26383(4) 0.0471(3) Uani d 1
O O3 1.11253(13) 1.39299(13) 0.47028(4) 0.0333(3) Uani d 1
O O4 1.22167(13) 1.66213(14) 0.46602(4) 0.0381(3) Uani d 1
N N1 0.60264(15) 0.57642(16) 0.34966(4) 0.0270(3) Uani d 1
H H1N 0.5994(18) 0.5906(19) 0.3166(3) 0.032 Uiso d 1
N N2 0.68109(14) 0.70148(15) 0.38056(4) 0.0255(3) Uani d 1
N N3 0.86691(14) 1.12670(15) 0.36312(4) 0.0251(3) Uani d 1
N N4 0.95062(15) 1.25696(15) 0.39075(4) 0.0251(3) Uani d 1
H H4N 0.9728(17) 1.2425(19) 0.4227(4) 0.030 Uiso d 1
N N5 0.41343(15) 0.30492(16) 0.28948(4) 0.0291(3) Uani d 1
N N6 1.14979(15) 1.53197(16) 0.44560(4) 0.0272(3) Uani d 1
C C1 0.53689(16) 0.42342(18) 0.37167(5) 0.0230(3) Uani d 1
C C2 0.44424(17) 0.29060(18) 0.34426(5) 0.0246(3) Uani d 1
C C3 0.37566(17) 0.13959(19) 0.36908(6) 0.0298(3) Uani d 1
H H3A 0.3147 0.0547 0.3500 0.036 Uiso calc 1
C C4 0.39677(19) 0.11451(19) 0.42111(6) 0.0331(4) Uani d 1
H H4A 0.3513 0.0132 0.4375 0.040 Uiso calc 1
C C5 0.48780(18) 0.24393(19) 0.44908(6) 0.0312(4) Uani d 1
H H5 0.5026 0.2282 0.4845 0.037 Uiso calc 1
C C6 0.55555(17) 0.39336(18) 0.42543(5) 0.0275(3) Uani d 1
H H6 0.6153 0.4772 0.4452 0.033 Uiso calc 1
C C7 0.73489(17) 0.84686(18) 0.35836(5) 0.0259(3) Uani d 1
H H7 0.7187 0.8640 0.3231 0.031 Uiso calc 1
C C8 0.82108(17) 0.98371(18) 0.38888(5) 0.0243(3) Uani d 1
C C9 1.01205(16) 1.40734(17) 0.36605(5) 0.0214(3) Uani d 1
C C10 1.10995(16) 1.54146(18) 0.39096(5) 0.0228(3) Uani d 1
C C11 1.17754(18) 1.68724(19) 0.36358(5) 0.0295(4) Uani d 1
H H11 1.2431 1.7730 0.3807 0.035 Uiso calc 1
C C12 1.1485(2) 1.7056(2) 0.31161(6) 0.0351(4) Uani d 1
H H12 1.1958 1.8016 0.2932 0.042 Uiso calc 1
C C13 1.04659(19) 1.5778(2) 0.28672(6) 0.0316(4) Uani d 1
H H13 1.0241 1.5908 0.2516 0.038 Uiso calc 1
C C14 0.97949(17) 1.43429(18) 0.31305(5) 0.0264(3) Uani d 1
H H14 0.9106 1.3523 0.2956 0.032 Uiso calc 1
C C15 0.85593(19) 0.9528(2) 0.44505(5) 0.0317(4) Uani d 1
H H15A 0.9751 0.9402 0.4503 0.048 Uiso calc 1
H H15B 0.8000 0.8438 0.4562 0.048 Uiso calc 1
H H15C 0.8151 1.0544 0.4647 0.048 Uiso calc 1
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
C1 N1 N2 118.98(11)
C1 N1 H1N 120.2(10)
N2 N1 H1N 120.7(10)
C7 N2 N1 116.67(12)
C8 N3 N4 115.84(11)
C9 N4 N3 119.74(11)
C9 N4 H4N 118.7(10)
N3 N4 H4N 121.3(10)
O1 N5 O2 121.46(12)
O1 N5 C2 119.35(12)
O2 N5 C2 119.19(12)
O4 N6 O3 121.98(11)
O4 N6 C10 118.74(11)
O3 N6 C10 119.28(11)
N1 C1 C2 124.03(12)
N1 C1 C6 119.91(12)
C2 C1 C6 116.03(12)
C3 C2 C1 121.55(13)
C3 C2 N5 116.41(12)
C1 C2 N5 122.04(12)
C4 C3 C2 120.84(13)
C4 C3 H3A 119.6
C2 C3 H3A 119.6
C3 C4 C5 118.71(14)
C3 C4 H4A 120.6
C5 C4 H4A 120.6
C6 C5 C4 121.28(14)
C6 C5 H5 119.4
C4 C5 H5 119.4
C5 C6 C1 121.58(13)
C5 C6 H6 119.2
C1 C6 H6 119.2
N2 C7 C8 119.36(13)
N2 C7 H7 120.3
C8 C7 H7 120.3
N3 C8 C7 114.54(12)
N3 C8 C15 124.77(12)
C7 C8 C15 120.66(12)
N4 C9 C14 120.20(12)
N4 C9 C10 123.28(12)
C14 C9 C10 116.52(12)
C11 C10 C9 121.22(12)
C11 C10 N6 116.67(12)
C9 C10 N6 122.08(12)
C12 C11 C10 120.66(13)
C12 C11 H11 119.7
C10 C11 H11 119.7
C11 C12 C13 118.87(14)
C11 C12 H12 120.6
C13 C12 H12 120.6
C14 C13 C12 121.10(14)
C14 C13 H13 119.5
C12 C13 H13 119.5
C13 C14 C9 121.53(13)
C13 C14 H14 119.2
C9 C14 H14 119.2
C8 C15 H15A 109.5
C8 C15 H15B 109.5
H15A C15 H15B 109.5
C8 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N5 1.2312(14)
O2 N5 1.2416(15)
O3 N6 1.2400(14)
O4 N6 1.2322(14)
N1 C1 1.3641(17)
N1 N2 1.3673(15)
N1 H1N 0.861(8)
N2 C7 1.2859(17)
N3 C8 1.2962(16)
N3 N4 1.3664(15)
N4 C9 1.3664(17)
N4 H4N 0.852(8)
N5 C2 1.4407(17)
N6 C10 1.4488(17)
C1 C2 1.4122(18)
C1 C6 1.4145(19)
C2 C3 1.3927(19)
C3 C4 1.368(2)
C3 H3A 0.9300
C4 C5 1.3959(19)
C4 H4A 0.9300
C5 C6 1.3672(19)
C5 H5 0.9300
C6 H6 0.9300
C7 C8 1.4495(19)
C7 H7 0.9300
C8 C15 1.4950(19)
C9 C14 1.4078(18)
C9 C10 1.4103(18)
C10 C11 1.3917(19)
C11 C12 1.369(2)
C11 H11 0.9300
C12 C13 1.396(2)
C12 H12 0.9300
C13 C14 1.3639(19)
C13 H13 0.9300
C14 H14 0.9300
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600

_cod_database_fobs_code 2020303
