#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:07:12 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179652 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/05/4510550.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_4510550
loop_
_publ_author_name
'Rubčić, Mirta'
'Galić, Nives'
'Halasz, Ivan'
'Jednačak, Tomislav'
'Judaš, Nenad'
'Plavec, Janez'
'Šket, Primož'
'Novak, Predrag'
_publ_section_title
;
 Multiple Solid Forms of 1,5-Bis(salicylidene)carbohydrazide:
 Polymorph-Modulated Thermal Reactivity
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2900
_journal_paper_doi               10.1021/cg500203k
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C15 H14 N4 O3'
_chemical_formula_sum            'C15 H14 N4 O3'
_chemical_formula_weight         298.30
_chemical_name_systematic        1,5-bis(salicylidene)carbohydrazide
_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                 97.649(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5804(12)
_cell_length_b                   15.7399(18)
_cell_length_c                   9.0114(11)
_cell_measurement_reflns_used    3613
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.9291
_cell_measurement_theta_min      4.2302
_cell_volume                     1487.4(3)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9886
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         4.34
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3072
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0416
_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)+(0.0604P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                2091
_reflns_number_total             3072
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg500203k_si_001.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 4510550--4510553.cif.'
_cod_database_code               4510550
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
N4 N 0.17724(10) 0.11073(7) 0.59675(11) 0.0530(3) Uani 1 1 d .
N1 N 0.30667(10) 0.39250(7) 0.57537(11) 0.0503(3) Uani 1 1 d .
C8 C 0.24145(11) 0.25250(8) 0.59182(12) 0.0458(3) Uani 1 1 d .
C7 C 0.32025(12) 0.45893(9) 0.49858(14) 0.0516(3) Uani 1 1 d .
H7 H 0.3003 0.4576 0.3949 0.062 Uiso 1 1 calc R
N3 N 0.22022(11) 0.17775(7) 0.51924(11) 0.0535(3) Uani 1 1 d D
H3N H 0.2248(13) 0.1745(9) 0.4293(14) 0.064 Uiso 1 1 d D
O2 O 0.24219(9) 0.25944(6) 0.72808(9) 0.0605(3) Uani 1 1 d .
N2 N 0.26426(11) 0.31912(7) 0.50452(11) 0.0535(3) Uani 1 1 d D
H2N H 0.2636(14) 0.3123(9) 0.4128(14) 0.064 Uiso 1 1 d D
C9 C 0.18332(14) 0.03667(9) 0.54169(15) 0.0563(4) Uani 1 1 d .
H9 H 0.2181 0.0295 0.4530 0.068 Uiso 1 1 calc R
C10 C 0.13661(13) -0.03700(9) 0.61563(15) 0.0556(4) Uani 1 1 d .
O3 O 0.03514(11) 0.04665(8) 0.79028(12) 0.0765(3) Uani 1 1 d D
H3O H 0.0666(17) 0.0865(10) 0.744(2) 0.092 Uiso 1 1 d D
O1 O 0.41830(13) 0.46739(8) 0.81301(11) 0.0829(4) Uani 1 1 d D
H1O H 0.3864(18) 0.4251(10) 0.765(2) 0.100 Uiso 1 1 d D
C6 C 0.36697(12) 0.53678(8) 0.57321(15) 0.0518(3) Uani 1 1 d .
C5 C 0.36674(15) 0.61217(10) 0.49295(18) 0.0668(4) Uani 1 1 d .
H5 H 0.3366 0.6121 0.3912 0.080 Uiso 1 1 calc R
C11 C 0.06605(14) -0.02983(9) 0.73537(17) 0.0598(4) Uani 1 1 d .
C1 C 0.41472(14) 0.53823(10) 0.72660(16) 0.0609(4) Uani 1 1 d .
C15 C 0.16294(16) -0.11828(10) 0.56607(19) 0.0726(4) Uani 1 1 d .
H15 H 0.2085 -0.1243 0.4853 0.087 Uiso 1 1 calc R
C12 C 0.02499(15) -0.10252(12) 0.80291(19) 0.0779(5) Uani 1 1 d .
H12 H -0.0222 -0.0976 0.8825 0.094 Uiso 1 1 calc R
C4 C 0.41009(16) 0.68683(10) 0.5608(2) 0.0797(5) Uani 1 1 d .
H4 H 0.4074 0.7370 0.5060 0.096 Uiso 1 1 calc R
C2 C 0.46054(16) 0.61336(12) 0.7932(2) 0.0802(5) Uani 1 1 d .
H2 H 0.4933 0.6139 0.8942 0.096 Uiso 1 1 calc R
C3 C 0.45799(17) 0.68654(12) 0.7120(2) 0.0850(5) Uani 1 1 d .
H3 H 0.4886 0.7367 0.7581 0.102 Uiso 1 1 calc R
C13 C 0.05410(17) -0.18144(12) 0.7521(2) 0.0836(5) Uani 1 1 d .
H13 H 0.0268 -0.2297 0.7981 0.100 Uiso 1 1 calc R
C14 C 0.12268(17) -0.18988(11) 0.6346(2) 0.0834(5) Uani 1 1 d .
H14 H 0.1421 -0.2436 0.6010 0.100 Uiso 1 1 calc R
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
C9 N4 N3 117.87(11)
C7 N1 N2 119.63(10)
O2 C8 N3 122.60(12)
O2 C8 N2 122.24(12)
N3 C8 N2 115.16(10)
N1 C7 C6 119.84(12)
N1 C7 H7 120.1
C6 C7 H7 120.1
C8 N3 N4 117.85(10)
C8 N3 H3N 120.4(10)
N4 N3 H3N 121.4(10)
C8 N2 N1 117.18(10)
C8 N2 H2N 119.9(10)
N1 N2 H2N 122.1(10)
N4 C9 C10 120.89(13)
N4 C9 H9 119.6
C10 C9 H9 119.6
C15 C10 C11 118.13(14)
C15 C10 C9 119.29(14)
C11 C10 C9 122.57(14)
C11 O3 H3O 110.4(13)
C1 O1 H1O 112.0(13)
C5 C6 C1 118.22(13)
C5 C6 C7 120.17(13)
C1 C6 C7 121.60(13)
C4 C5 C6 121.41(16)
C4 C5 H5 119.3
C6 C5 H5 119.3
O3 C11 C12 117.70(14)
O3 C11 C10 122.19(13)
C12 C11 C10 120.11(15)
O1 C1 C2 118.14(14)
O1 C1 C6 121.94(13)
C2 C1 C6 119.92(15)
C14 C15 C10 121.28(17)
C14 C15 H15 119.4
C10 C15 H15 119.4
C13 C12 C11 120.04(17)
C13 C12 H12 120.0
C11 C12 H12 120.0
C5 C4 C3 119.33(16)
C5 C4 H4 120.3
C3 C4 H4 120.3
C3 C2 C1 120.55(16)
C3 C2 H2 119.7
C1 C2 H2 119.7
C2 C3 C4 120.54(16)
C2 C3 H3 119.7
C4 C3 H3 119.7
C14 C13 C12 120.80(16)
C14 C13 H13 119.6
C12 C13 H13 119.6
C13 C14 C15 119.63(17)
C13 C14 H14 120.2
C15 C14 H14 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N4 C9 1.2718(17)
N4 N3 1.3755(15)
N1 C7 1.2724(16)
N1 N2 1.3663(14)
C8 O2 1.2316(13)
C8 N3 1.3504(16)
C8 N2 1.3518(16)
C7 C6 1.4524(18)
C7 H7 0.9300
N3 H3N 0.820(12)
N2 H2N 0.832(12)
C9 C10 1.4561(19)
C9 H9 0.9300
C10 C15 1.395(2)
C10 C11 1.396(2)
O3 C11 1.3580(18)
O3 H3O 0.844(14)
O1 C1 1.3576(18)
O1 H1O 0.841(14)
C6 C5 1.3895(19)
C6 C1 1.4074(19)
C5 C4 1.375(2)
C5 H5 0.9300
C11 C12 1.392(2)
C1 C2 1.384(2)
C15 C14 1.379(2)
C15 H15 0.9300
C12 C13 1.373(2)
C12 H12 0.9300
C4 C3 1.389(2)
C4 H4 0.9300
C2 C3 1.363(2)
C2 H2 0.9300
C3 H3 0.9300
C13 C14 1.367(3)
C13 H13 0.9300
C14 H14 0.9300
