#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:27:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178479 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/00/4030068.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_4030068
loop_
_publ_author_name
'Zhang, Xinting'
'Kang, Jinfeng'
'Niu, Pengfei'
'Wu, Jie'
'Yu, Wenquan'
'Chang, Junbiao'
_publ_section_title
;
 I2-Mediated Oxidative C-N Bond Formation for Metal-Free One-Pot Synthesis
 of Di-, Tri-, and Tetrasubstituted Pyrazoles from α,β-Unsaturated
 Aldehydes/Ketones and Hydrazines.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10170
_journal_paper_doi               10.1021/jo501844x
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C16 H11 N3'
_chemical_formula_weight         245.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_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                113.94(3)
_cell_angle_beta                 92.53(3)
_cell_angle_gamma                92.22(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9756(14)
_cell_length_b                   9.910(2)
_cell_length_c                   10.420(2)
_cell_measurement_temperature    293(2)
_cell_volume                     656.4(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6416
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.076
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0596
_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)+(0.0776P)²+0.0914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1771
_reflns_number_gt                2390
_reflns_number_total             3049
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501844x_si_002.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 4030067--4030068.cif.'
_cod_original_cell_volume        656.4(2)
_cod_database_code               4030068
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 0.3651(2) 0.19956(15) 0.72863(14) 0.0547(4) Uani 1 1 d .
N2 N 0.2362(2) 0.27369(18) 0.68171(17) 0.0669(4) Uani 1 1 d .
N3 N 0.2167(3) -0.5445(2) 0.4092(2) 0.0943(6) Uani 1 1 d .
C1 C 0.3077(3) 0.4123(2) 0.7365(2) 0.0689(5) Uani 1 1 d .
H1 H 0.2498 0.4891 0.7234 0.083 Uiso 1 1 calc R
C2 C 0.4797(3) 0.4300(2) 0.81631(19) 0.0649(5) Uani 1 1 d .
H2 H 0.5557 0.5171 0.8634 0.078 Uiso 1 1 calc R
C3 C 0.5142(3) 0.29250(17) 0.81133(16) 0.0546(4) Uani 1 1 d .
C4 C 0.6654(2) 0.25369(17) 0.89218(17) 0.0544(4) Uani 1 1 d .
C5 C 0.8538(3) 0.3039(2) 0.8951(2) 0.0698(5) Uani 1 1 d .
H5 H 0.8856 0.3538 0.8395 0.084 Uiso 1 1 calc R
C6 C 0.9953(3) 0.2810(3) 0.9795(3) 0.0847(6) Uani 1 1 d .
H6 H 1.1215 0.3153 0.9803 0.102 Uiso 1 1 calc R
C7 C 0.9502(4) 0.2072(3) 1.0630(3) 0.0875(7) Uani 1 1 d .
H7 H 1.0457 0.1918 1.1199 0.105 Uiso 1 1 calc R
C8 C 0.7621(4) 0.1565(2) 1.0613(2) 0.0807(6) Uani 1 1 d .
H8 H 0.7308 0.1068 1.1172 0.097 Uiso 1 1 calc R
C9 C 0.6203(3) 0.1795(2) 0.9764(2) 0.0662(5) Uani 1 1 d .
H9 H 0.4940 0.1453 0.9756 0.079 Uiso 1 1 calc R
C10 C 0.3376(2) 0.04279(18) 0.67191(16) 0.0526(4) Uani 1 1 d .
C11 C 0.1510(3) -0.0209(2) 0.6373(2) 0.0652(5) Uani 1 1 d .
H11 H 0.0470 0.0387 0.6580 0.078 Uiso 1 1 calc R
C12 C 0.1208(3) -0.1721(2) 0.5723(2) 0.0699(5) Uani 1 1 d .
H12 H -0.0039 -0.2148 0.5479 0.084 Uiso 1 1 calc R
C13 C 0.2755(3) -0.26130(19) 0.54314(18) 0.0616(5) Uani 1 1 d .
C14 C 0.4614(3) -0.1972(2) 0.58168(19) 0.0631(5) Uani 1 1 d .
H14 H 0.5651 -0.2570 0.5650 0.076 Uiso 1 1 calc R
C15 C 0.4930(3) -0.04572(19) 0.64438(18) 0.0587(4) Uani 1 1 d .
H15 H 0.6177 -0.0030 0.6681 0.070 Uiso 1 1 calc R
C16 C 0.2436(3) -0.4199(2) 0.4691(2) 0.0725(5) Uani 1 1 d .
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 111.65(14)
C3 N1 C10 130.79(14)
N2 N1 C10 117.01(14)
C1 N2 N1 104.36(15)
N2 C1 C2 112.17(16)
N2 C1 H1 123.9
C2 C1 H1 123.9
C3 C2 C1 105.95(17)
C3 C2 H2 127.0
C1 C2 H2 127.0
N1 C3 C2 105.87(16)
N1 C3 C4 125.90(14)
C2 C3 C4 127.80(16)
C5 C4 C9 118.82(17)
C5 C4 C3 119.43(16)
C9 C4 C3 121.46(16)
C6 C5 C4 120.8(2)
C6 C5 H5 119.6
C4 C5 H5 119.6
C5 C6 C7 120.2(2)
C5 C6 H6 119.9
C7 C6 H6 119.9
C6 C7 C8 119.6(2)
C6 C7 H7 120.2
C8 C7 H7 120.2
C7 C8 C9 120.1(2)
C7 C8 H8 120.0
C9 C8 H8 120.0
C8 C9 C4 120.47(19)
C8 C9 H9 119.8
C4 C9 H9 119.8
C15 C10 C11 120.30(16)
C15 C10 N1 121.06(15)
C11 C10 N1 118.56(16)
C12 C11 C10 119.79(18)
C12 C11 H11 120.1
C10 C11 H11 120.1
C11 C12 C13 120.24(17)
C11 C12 H12 119.9
C13 C12 H12 119.9
C12 C13 C14 119.69(17)
C12 C13 C16 120.07(17)
C14 C13 C16 120.21(18)
C15 C14 C13 120.38(18)
C15 C14 H14 119.8
C13 C14 H14 119.8
C14 C15 C10 119.56(17)
C14 C15 H15 120.2
C10 C15 H15 120.2
N3 C16 C13 178.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C3 1.369(2)
N1 N2 1.375(2)
N1 C10 1.422(2)
N2 C1 1.322(3)
N3 C16 1.138(2)
C1 C2 1.392(3)
C1 H1 0.9300
C2 C3 1.373(2)
C2 H2 0.9300
C3 C4 1.479(2)
C4 C5 1.382(3)
C4 C9 1.392(3)
C5 C6 1.379(3)
C5 H5 0.9300
C6 C7 1.383(4)
C6 H6 0.9300
C7 C8 1.384(3)
C7 H7 0.9300
C8 C9 1.385(3)
C8 H8 0.9300
C9 H9 0.9300
C10 C15 1.387(2)
C10 C11 1.390(2)
C11 C12 1.374(3)
C11 H11 0.9300
C12 C13 1.387(3)
C12 H12 0.9300
C13 C14 1.389(3)
C13 C16 1.445(3)
C14 C15 1.376(2)
C14 H14 0.9300
C15 H15 0.9300
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
C3 N1 N2 C1 -0.09(19)
C10 N1 N2 C1 -172.55(15)
N1 N2 C1 C2 0.6(2)
N2 C1 C2 C3 -0.9(2)
N2 N1 C3 C2 -0.43(19)
C10 N1 C3 C2 170.68(16)
N2 N1 C3 C4 172.48(15)
C10 N1 C3 C4 -16.4(3)
C1 C2 C3 N1 0.8(2)
C1 C2 C3 C4 -171.98(17)
N1 C3 C4 C5 138.68(19)
C2 C3 C4 C5 -50.0(3)
N1 C3 C4 C9 -47.5(3)
C2 C3 C4 C9 123.9(2)
C9 C4 C5 C6 0.1(3)
C3 C4 C5 C6 174.12(18)
C4 C5 C6 C7 -0.1(3)
C5 C6 C7 C8 0.0(4)
C6 C7 C8 C9 0.0(4)
C7 C8 C9 C4 0.0(3)
C5 C4 C9 C8 -0.1(3)
C3 C4 C9 C8 -173.96(17)
C3 N1 C10 C15 -27.2(3)
N2 N1 C10 C15 143.47(16)
C3 N1 C10 C11 156.17(17)
N2 N1 C10 C11 -33.1(2)
C15 C10 C11 C12 -1.6(3)
N1 C10 C11 C12 175.01(16)
C10 C11 C12 C13 0.9(3)
C11 C12 C13 C14 0.9(3)
C11 C12 C13 C16 -177.17(17)
C12 C13 C14 C15 -2.1(3)
C16 C13 C14 C15 175.95(16)
C13 C14 C15 C10 1.5(3)
C11 C10 C15 C14 0.4(3)
N1 C10 C15 C14 -176.13(15)
C12 C13 C16 N3 51(14)
C14 C13 C16 N3 -127(14)
