#------------------------------------------------------------------------------
#$Date: 2019-10-04 07:23:49 +0300 (Fri, 04 Oct 2019) $
#$Revision: 219090 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/23/1552370.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_1552370
loop_
_publ_author_name
'El Alami, Abouelhaoul'
'Hamid, Sdassi'
'El Kihel, Abdellatif'
'Saadi, Mohamed'
'El Ammari, Lahcen'
_publ_section_title
;
 3,3'-[(1E,1'E)-Hydrazine-1,2-diylidenebis(ethan-1-yl-1-ylidene)]bis(4-hydroxy-6-methyl-2H-pyran-2-one)
;
_journal_coeditor_code           SJ4210
_journal_issue                   10
_journal_name_full               IUCrData
_journal_page_first              x191348
_journal_paper_doi               10.1107/S2414314619013488
_journal_volume                  4
_journal_year                    2019
_chemical_formula_iupac          'C16 H16 N2 O6'
_chemical_formula_moiety         'C16 H16 N2 O6'
_chemical_formula_sum            'C16 H16 N2 O6'
_chemical_formula_weight         332.31
_chemical_name_systematic
3,3'-[(1E,1'E)-Hydrazine-1,2-diylidenebis(ethan-1-yl-1-ylidene)]bis(4-hydroxy-6-methyl-2H-pyran-2-one)
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 110.642(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.797(3)
_cell_length_b                   3.9750(4)
_cell_length_c                   14.4569(15)
_cell_measurement_reflns_used    1626
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.093
_cell_measurement_theta_min      3.013
_cell_volume                     1494.8(3)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
WinGX and ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
Mercury (Macrae et al., 2008) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXTL2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'PHOTON100 CMOS area-detector'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE Super DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'HELIOS mirror optics'
_diffrn_radiation_source         'INCOATEC I\mS micro-focus source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15395
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.097
_diffrn_reflns_theta_min         3.011
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       Block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.231
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2018/3 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0725P)²+1.6983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1482
_reflns_number_gt                1221
_reflns_number_total             1627
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sj4210sup1.cif
_cod_data_source_block           I
_cod_database_code               1552370
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.31666(5) 0.5614(4) 0.29992(10) 0.0404(4) Uani d 1
O O2 0.44045(5) 0.0821(4) 0.27764(9) 0.0486(5) Uani d 1
H H2 0.462232 0.040600 0.331799 0.073 Uiso calc 1
O O3 0.34743(6) 0.5875(5) 0.46061(11) 0.0582(5) Uani d 1
N N1 0.47971(5) 0.0522(4) 0.45929(10) 0.0318(4) Uani d 1
C C1 0.27228(8) 0.5809(6) 0.12749(15) 0.0467(6) Uani d 1
H H1A 0.277478 0.547070 0.065932 0.070 Uiso calc 1
H H1C 0.265360 0.814272 0.134436 0.070 Uiso calc 1
H H1B 0.243653 0.447745 0.128495 0.070 Uiso calc 1
C C2 0.31917(7) 0.4781(5) 0.21031(13) 0.0340(5) Uani d 1
C C3 0.35979(7) 0.3216(5) 0.20315(13) 0.0365(5) Uani d 1
H H3 0.360757 0.268689 0.141167 0.044 Uiso calc 1
C C4 0.40194(7) 0.2338(5) 0.28963(13) 0.0331(5) Uani d 1
C C5 0.40009(6) 0.3095(5) 0.38391(12) 0.0289(4) Uani d 1
C C6 0.44140(7) 0.2111(5) 0.47291(12) 0.0286(4) Uani d 1
C C7 0.35581(7) 0.4878(5) 0.38895(13) 0.0350(5) Uani d 1
C C8 0.44100(8) 0.2785(6) 0.57414(14) 0.0462(6) Uani d 1
H H8A 0.445878 0.071299 0.610416 0.069 Uiso calc 1
H H8B 0.408612 0.375886 0.569385 0.069 Uiso calc 1
H H8C 0.468260 0.431695 0.607768 0.069 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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C2 O1 C7 . 122.85(15)
C4 O2 H2 . 109.5
C6 N1 N1 5_656 118.75(18)
C2 C1 H1A . 109.5
C2 C1 H1C . 109.5
H1A C1 H1C . 109.5
C2 C1 H1B . 109.5
H1A C1 H1B . 109.5
H1C C1 H1B . 109.5
C3 C2 O1 . 121.28(16)
C3 C2 C1 . 126.66(18)
O1 C2 C1 . 112.07(17)
C2 C3 C4 . 120.47(17)
C2 C3 H3 . 119.8
C4 C3 H3 . 119.8
O2 C4 C5 . 122.80(16)
O2 C4 C3 . 117.46(16)
C5 C4 C3 . 119.73(17)
C4 C5 C6 . 120.89(16)
C4 C5 C7 . 118.31(16)
C6 C5 C7 . 120.80(15)
N1 C6 C5 . 115.43(15)
N1 C6 C8 . 121.41(16)
C5 C6 C8 . 123.15(16)
O3 C7 O1 . 113.60(16)
O3 C7 C5 . 129.10(17)
O1 C7 C5 . 117.30(15)
C6 C8 H8A . 109.5
C6 C8 H8B . 109.5
H8A C8 H8B . 109.5
C6 C8 H8C . 109.5
H8A C8 H8C . 109.5
H8B C8 H8C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C2 . 1.363(2)
O1 C7 . 1.392(2)
O2 C4 . 1.293(2)
O2 H2 . 0.8200
O3 C7 . 1.206(2)
N1 C6 . 1.311(2)
N1 N1 5_656 1.376(3)
C1 C2 . 1.483(3)
C1 H1A . 0.9600
C1 H1C . 0.9600
C1 H1B . 0.9600
C2 C3 . 1.325(3)
C3 C4 . 1.423(2)
C3 H3 . 0.9300
C4 C5 . 1.414(2)
C5 C6 . 1.444(2)
C5 C7 . 1.444(3)
C6 C8 . 1.492(2)
C8 H8A . 0.9600
C8 H8B . 0.9600
C8 H8C . 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H2 N1 . 0.82 1.73 2.4659(18) 148
C3 H3 O3 6_565 0.93 2.57 3.420(2) 152
C8 H8A O2 6_556 0.96 2.55 3.278(2) 133
C8 H8B O3 . 0.96 2.05 2.821(3) 136
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_site_symmetry_1
_geom_torsion
C7 O1 C2 C3 . -0.3(3)
C7 O1 C2 C1 . 179.27(17)
O1 C2 C3 C4 . 0.5(3)
C1 C2 C3 C4 . -179.1(2)
C2 C3 C4 O2 . -179.86(19)
C2 C3 C4 C5 . 1.0(3)
O2 C4 C5 C6 . -1.6(3)
C3 C4 C5 C6 . 177.46(17)
O2 C4 C5 C7 . 178.38(19)
C3 C4 C5 C7 . -2.5(3)
N1 N1 C6 C5 5_656 -179.43(19)
N1 N1 C6 C8 5_656 -0.2(3)
C4 C5 C6 N1 . 0.4(3)
C7 C5 C6 N1 . -179.64(17)
C4 C5 C6 C8 . -178.80(18)
C7 C5 C6 C8 . 1.2(3)
C2 O1 C7 O3 . 178.35(18)
C2 O1 C7 C5 . -1.2(3)
C4 C5 C7 O3 . -176.9(2)
C6 C5 C7 O3 . 3.1(3)
C4 C5 C7 O1 . 2.6(3)
C6 C5 C7 O1 . -177.38(16)

_cod_database_fobs_code 1552370
