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#$Date: 2016-03-21 04:11:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178461 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/82/4028251.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_4028251
loop_
_publ_author_name
'S. Vijay Kumar'
'Santosh K. Yadav'
'B. Raghava'
'B. Saraiah'
'H. Ila'
'K. S. Rangappa'
'Arpan Hazra'
_publ_section_title
;
 Cyclocondensation of Arylhydrazines with
 1,3-Bis(het)arylmonothio-1,3-diketones and
 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of
 1-Aryl-3,5-bis(het)arylpyrazoles with Complementary Regioselectivity
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4960
_journal_page_last               4973
_journal_paper_doi               10.1021/jo400599e
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C23 H18 N4'
_chemical_formula_weight         350.41
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.267(4)
_cell_angle_beta                 69.494(3)
_cell_angle_gamma                71.237(3)
_cell_formula_units_Z            2
_cell_length_a                   9.3639(16)
_cell_length_b                   10.2100(18)
_cell_length_c                   10.8034(18)
_cell_measurement_temperature    293(2)
_cell_volume                     894.3(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_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  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0616
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6024
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.079
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             368
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0648
_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)+(0.1419P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1834
_refine_ls_wR_factor_ref         0.2372
_reflns_number_gt                2340
_reflns_number_total             4264
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400599e_si_002_6.cif
_cod_data_source_block           compound9i
_cod_database_code               4028251
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_refinement_flags
N1 N 0.5695(2) 0.1701(2) 0.2161(2) 0.0452(5) Uani 1 1 d .
N2 N 0.4391(2) 0.2491(2) 0.1753(2) 0.0475(6) Uani 1 1 d .
N3 N 1.0316(2) 0.0867(2) 0.2963(2) 0.0486(6) Uani 1 1 d .
N4 N 0.1827(3) 0.7474(3) 0.0965(3) 0.0646(7) Uani 1 1 d .
C1 C 0.4264(3) 0.3808(3) 0.1813(2) 0.0450(6) Uani 1 1 d .
C10 C 0.8226(3) 0.2555(3) 0.3731(2) 0.0431(6) Uani 1 1 d .
C3 C 0.6393(3) 0.2494(3) 0.2473(3) 0.0462(6) Uani 1 1 d .
C13 C 0.6051(3) 0.0202(3) 0.2288(3) 0.0454(6) Uani 1 1 d .
C5 C 0.7410(3) 0.3597(3) 0.4501(3) 0.0517(7) Uani 1 1 d .
H5 H 0.6376 0.4076 0.4520 0.062 Uiso 1 1 calc R
C2 C 0.5497(3) 0.3840(3) 0.2261(3) 0.0495(7) Uani 1 1 d .
H2 H 0.5665 0.4634 0.2387 0.059 Uiso 1 1 calc R
C9 C 0.9146(3) 0.0945(3) 0.2451(3) 0.0500(7) Uani 1 1 d .
H9 H 0.9221 0.0380 0.1888 0.060 Uiso 1 1 calc R
C11 C 0.9778(3) 0.1843(3) 0.3756(2) 0.0453(6) Uani 1 1 d .
C22 C 0.2980(4) 0.6369(3) 0.1255(3) 0.0570(7) Uani 1 1 d .
H22 H 0.3855 0.6554 0.1325 0.068 Uiso 1 1 calc R
C4 C 0.7848(3) 0.1967(3) 0.2877(3) 0.0460(6) Uani 1 1 d .
C23 C 0.2971(3) 0.4963(3) 0.1459(2) 0.0448(6) Uani 1 1 d .
C18 C 0.6115(3) -0.0300(3) 0.1220(3) 0.0558(7) Uani 1 1 d .
H18 H 0.6011 0.0322 0.0407 0.067 Uiso 1 1 calc R
C19 C 0.1654(3) 0.4703(3) 0.1357(3) 0.0572(7) Uani 1 1 d .
H19 H 0.1586 0.3780 0.1486 0.069 Uiso 1 1 calc R
C14 C 0.6259(3) -0.0713(3) 0.3483(3) 0.0607(8) Uani 1 1 d .
H14 H 0.6239 -0.0366 0.4193 0.073 Uiso 1 1 calc R
C12 C 1.1873(3) -0.0080(3) 0.2707(3) 0.0610(8) Uani 1 1 d .
H12A H 1.2469 0.0070 0.3194 0.092 Uiso 1 1 calc R
H12B H 1.2396 0.0108 0.1755 0.092 Uiso 1 1 calc R
H12C H 1.1783 -0.1044 0.3002 0.092 Uiso 1 1 calc R
C21 C 0.0592(4) 0.7187(4) 0.0871(3) 0.0679(9) Uani 1 1 d .
H21 H -0.0227 0.7941 0.0665 0.081 Uiso 1 1 calc R
C7 C 0.9708(4) 0.3177(4) 0.5229(3) 0.0657(9) Uani 1 1 d .
H7 H 1.0184 0.3403 0.5736 0.079 Uiso 1 1 calc R
C8 C 1.0543(4) 0.2144(3) 0.4504(3) 0.0557(7) Uani 1 1 d .
H8 H 1.1570 0.1664 0.4510 0.067 Uiso 1 1 calc R
C6 C 0.8175(4) 0.3893(3) 0.5227(3) 0.0605(8) Uani 1 1 d .
H6 H 0.7650 0.4591 0.5727 0.073 Uiso 1 1 calc R
C20 C 0.0455(4) 0.5832(4) 0.1062(3) 0.0700(9) Uani 1 1 d .
H20 H -0.0440 0.5683 0.0991 0.084 Uiso 1 1 calc R
C17 C 0.6337(4) -0.1739(3) 0.1366(4) 0.0691(9) Uani 1 1 d .
H17 H 0.6369 -0.2092 0.0656 0.083 Uiso 1 1 calc R
C15 C 0.6498(4) -0.2144(4) 0.3615(4) 0.0748(10) Uani 1 1 d .
H15 H 0.6649 -0.2769 0.4414 0.090 Uiso 1 1 calc R
C16 C 0.6512(4) -0.2649(3) 0.2577(4) 0.0770(10) Uani 1 1 d .
H16 H 0.6641 -0.3615 0.2685 0.092 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 N1 N2 112.6(2)
C3 N1 C13 130.3(2)
N2 N1 C13 116.93(18)
C1 N2 N1 104.91(19)
C9 N3 C11 108.3(2)
C9 N3 C12 126.0(2)
C11 N3 C12 125.7(2)
C21 N4 C22 116.6(3)
N2 C1 C2 110.0(2)
N2 C1 C23 120.6(2)
C2 C1 C23 129.4(2)
C11 C10 C5 118.5(2)
C11 C10 C4 106.6(2)
C5 C10 C4 134.9(2)
C2 C3 N1 105.4(2)
C2 C3 C4 129.1(2)
N1 C3 C4 125.5(2)
C18 C13 C14 120.9(3)
C18 C13 N1 118.8(2)
C14 C13 N1 120.3(2)
C6 C5 C10 118.6(3)
C3 C2 C1 107.2(2)
N3 C9 C4 110.7(2)
N3 C11 C8 129.3(3)
N3 C11 C10 108.2(2)
C8 C11 C10 122.5(3)
N4 C22 C23 124.8(3)
C9 C4 C10 106.3(2)
C9 C4 C3 128.8(2)
C10 C4 C3 124.6(2)
C22 C23 C19 117.0(3)
C22 C23 C1 121.5(2)
C19 C23 C1 121.6(2)
C13 C18 C17 119.4(3)
C20 C19 C23 118.9(3)
C15 C14 C13 119.3(3)
N4 C21 C20 123.5(3)
C8 C7 C6 121.7(3)
C7 C8 C11 117.0(3)
C5 C6 C7 121.6(3)
C19 C20 C21 119.3(3)
C18 C17 C16 119.4(3)
C16 C15 C14 120.2(3)
C15 C16 C17 120.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C3 1.362(3)
N1 N2 1.364(3)
N1 C13 1.432(3)
N2 C1 1.332(3)
N3 C9 1.362(3)
N3 C11 1.370(3)
N3 C12 1.453(3)
N4 C21 1.324(4)
N4 C22 1.332(4)
C1 C2 1.411(3)
C1 C23 1.461(3)
C10 C11 1.406(4)
C10 C5 1.407(4)
C10 C4 1.428(3)
C3 C2 1.359(4)
C3 C4 1.463(4)
C13 C18 1.375(4)
C13 C14 1.379(4)
C5 C6 1.376(4)
C9 C4 1.364(4)
C11 C8 1.400(4)
C22 C23 1.386(4)
C23 C19 1.388(4)
C18 C17 1.382(4)
C19 C20 1.373(4)
C14 C15 1.374(4)
C21 C20 1.377(4)
C7 C8 1.371(4)
C7 C6 1.387(4)
C17 C16 1.384(5)
C15 C16 1.363(5)
