#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/26/4502697.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_4502697
loop_
_publ_author_name
'Varughese, Sunil'
'Draper, Sylvia M.'
_publ_section_title
;
 Pyridazines in Crystal Engineering. A Systematic Evaluation of the Role
 of Isomerism and Steric Factors in Determining Crystal Packing and
 Nano/Microcrystal Morphologies
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2571
_journal_paper_doi               10.1021/cg9015383
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         'C34 H22 N8, 2(C H4 O)'
_chemical_formula_sum            'C36 H30 N8 O2'
_chemical_formula_weight         606.68
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            9
_cell_length_a                   35.650(5)
_cell_length_b                   35.650(5)
_cell_length_c                   6.306(2)
_cell_measurement_reflns_used    6751
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      2.26
_cell_volume                     6941(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0719
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            28713
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.9791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Sheldrick, 1996'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Blocks
_exptl_crystal_F_000             2862
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0705
_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)+(0.0899P)²+19.6450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1896
_refine_ls_wR_factor_ref         0.1982
_reflns_number_gt                3139
_reflns_number_total             3840
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg9015383_si_003.cif
_cod_data_source_block           2a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'multi scan'
changed to 'multi-scan' 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 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4502697
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
C26 C 0.54330(8) 0.41660(8) -0.3413(5) 0.0367(7) Uani 1 1 d .
H26 H 0.5134 0.3965 -0.3607 0.044 Uiso 1 1 calc R
C25 C 0.57212(9) 0.41629(9) -0.4868(5) 0.0355(6) Uani 1 1 d .
H25 H 0.5622 0.3965 -0.6021 0.043 Uiso 1 1 calc R
C24 C 0.61545(8) 0.44526(8) -0.4608(4) 0.0275(5) Uani 1 1 d .
H24 H 0.6362 0.4459 -0.5578 0.033 Uiso 1 1 calc R
C23 C 0.62837(7) 0.47347(7) -0.2903(4) 0.0213(5) Uani 1 1 d .
H23 H 0.6581 0.4938 -0.2680 0.026 Uiso 1 1 calc R
C34 C 0.71954(7) 0.61289(7) 0.8222(4) 0.0228(5) Uani 1 1 d .
H34 H 0.7477 0.6208 0.8714 0.027 Uiso 1 1 calc R
C36 C 0.65321(7) 0.61276(7) 0.8549(3) 0.0224(5) Uani 1 1 d .
H36 H 0.6356 0.6212 0.9309 0.027 Uiso 1 1 calc R
C35 C 0.69394(7) 0.62482(7) 0.9358(4) 0.0227(5) Uani 1 1 d .
H35 H 0.7039 0.6407 1.0644 0.027 Uiso 1 1 calc R
C42 C 0.50479(6) 0.48707(7) 0.1999(3) 0.0167(4) Uani 1 1 d .
H42 H 0.5080 0.4781 0.3375 0.020 Uiso 1 1 calc R
C13 C 0.60998(6) 0.50086(6) 0.0349(3) 0.0159(4) Uani 1 1 d .
C22 C 0.59705(7) 0.47159(6) -0.1520(3) 0.0178(4) Uani 1 1 d .
C16 C 0.64248(6) 0.55128(6) 0.3791(3) 0.0157(4) Uani 1 1 d .
C33 C 0.70396(7) 0.58942(7) 0.6373(4) 0.0202(4) Uani 1 1 d .
H33 H 0.7212 0.5811 0.5573 0.024 Uiso 1 1 calc R
C32 C 0.66226(6) 0.57818(6) 0.5704(3) 0.0159(4) Uani 1 1 d .
C46 C 0.53480(6) 0.51822(7) -0.1388(3) 0.0170(4) Uani 1 1 d .
H46 H 0.5586 0.5307 -0.2345 0.020 Uiso 1 1 calc R
C41 C 0.54006(6) 0.50531(6) 0.0625(3) 0.0147(4) Uani 1 1 d .
C14 C 0.58328(6) 0.51410(6) 0.1368(3) 0.0148(4) Uani 1 1 d .
C15 C 0.60036(6) 0.53909(6) 0.3161(3) 0.0151(4) Uani 1 1 d .
H15 H 0.5836 0.5480 0.3962 0.018 Uiso 1 1 calc R
C90 C 0.37927(17) 0.61471(17) 0.9478(7) 0.0779(13) Uani 1 1 d .
H90A H 0.3640 0.6233 1.0488 0.117 Uiso 1 1 calc R
H90B H 0.4090 0.6253 0.9972 0.117 Uiso 1 1 calc R
H90C H 0.3641 0.5831 0.9366 0.117 Uiso 1 1 calc R
N21 N 0.55475(6) 0.44331(6) -0.1754(4) 0.0275(5) Uani 1 1 d .
N12 N 0.65028(6) 0.51369(6) 0.1025(3) 0.0193(4) Uani 1 1 d .
N31 N 0.63728(6) 0.58998(6) 0.6765(3) 0.0187(4) Uani 1 1 d .
N11 N 0.66690(6) 0.53928(6) 0.2707(3) 0.0198(4) Uani 1 1 d .
O90 O 0.38027(9) 0.63282(8) 0.7457(4) 0.0596(7) Uani 1 1 d .
H90 H 0.3581 0.6156 0.6766 0.089 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
_geom_angle_site_symmetry_1
N21 C26 C25 124.3(2) .
C24 C25 C26 118.4(2) .
C25 C24 C23 118.7(2) .
C24 C23 C22 119.0(2) .
C33 C34 C35 119.8(2) .
N31 C36 C35 123.9(2) .
C34 C35 C36 117.6(2) .
C46 C42 C41 120.82(19) 10_665
N12 C13 C14 121.89(19) .
N12 C13 C22 113.25(17) .
C14 C13 C22 124.86(18) .
N21 C22 C23 122.8(2) .
N21 C22 C13 116.95(18) .
C23 C22 C13 120.21(19) .
N11 C16 C15 121.79(19) .
N11 C16 C32 116.68(18) .
C15 C16 C32 121.54(18) .
C34 C33 C32 118.5(2) .
N31 C32 C33 122.58(19) .
N31 C32 C16 115.72(18) .
C33 C32 C16 121.68(19) .
C42 C46 C41 120.36(18) 10_665
C42 C41 C46 118.82(18) .
C42 C41 C14 120.08(18) .
C46 C41 C14 120.90(18) .
C15 C14 C13 115.83(18) .
C15 C14 C41 118.12(18) .
C13 C14 C41 125.98(18) .
C14 C15 C16 119.57(18) .
C26 N21 C22 116.8(2) .
N11 N12 C13 121.43(18) .
C36 N31 C32 117.66(19) .
N12 N11 C16 119.36(17) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C26 N21 1.334(3) .
C26 C25 1.382(4) .
C25 C24 1.373(4) .
C24 C23 1.384(3) .
C23 C22 1.392(3) .
C34 C33 1.379(3) .
C34 C35 1.384(3) .
C36 N31 1.336(3) .
C36 C35 1.389(3) .
C42 C46 1.382(3) 10_665
C42 C41 1.392(3) .
C13 N12 1.341(3) .
C13 C14 1.411(3) .
C13 C22 1.487(3) .
C22 N21 1.338(3) .
C16 N11 1.335(3) .
C16 C15 1.396(3) .
C16 C32 1.482(3) .
C33 C32 1.397(3) .
C32 N31 1.339(3) .
C46 C42 1.382(3) 10_665
C46 C41 1.394(3) .
C41 C14 1.486(3) .
C14 C15 1.378(3) .
C90 O90 1.421(5) .
N12 N11 1.329(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145005
