#------------------------------------------------------------------------------
#$Date: 2021-09-27 11:51:07 +0300 (Mon, 27 Sep 2021) $
#$Revision: 269318 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/47/1564726.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_1564726
loop_
_publ_author_name
'Medrano-Castillo, Layla J.'
'Collazo-Flores, Miguel Á.'
'Camarena-Díaz, Juan P.'
'Correa-Ayala, Erick'
'Chávez, Daniel'
'Grotjahn, Douglas B.'
'Rheingold, Arnold L.'
'Miranda-Soto, Valentín'
'Parra-Hake, Miguel'
_publ_section_title
;
 Base-free transfer hydrogenation of aryl-ketones, alkyl-ketones and
 alkenones catalyzed by an IrIIICp* complex bearing a triazenide ligand
 functionalized with pyrazole
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119551
_journal_paper_doi               10.1016/j.ica.2020.119551
_journal_volume                  507
_journal_year                    2020
_chemical_formula_sum            'C11 H13 N5'
_chemical_formula_weight         215.26
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 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                 106.847(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.277(3)
_cell_length_b                   5.6216(13)
_cell_length_c                   14.489(2)
_cell_measurement_reflns_used    1279
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.23
_cell_measurement_theta_min      2.38
_cell_volume                     1113.0(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5790
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.65
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_correction_T_min  0.9933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2096
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0629P)²+0.0290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1152
_reflns_number_gt                1443
_reflns_number_total             2096
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ICA-2020-507-119551.cif
_cod_data_source_block           grot423
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8369 2020-08-20 11:38:08Z andrius 
;
_cod_original_cell_volume        1112.9(4)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1564726
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.36741(10) 0.6276(3) 0.25144(10) 0.0196(4) Uani 1 1 d . . .
N2 N 0.40170(10) 0.4209(3) 0.29697(10) 0.0197(4) Uani 1 1 d . . .
N3 N 0.42332(9) 0.2568(3) 0.44977(9) 0.0186(4) Uani 1 1 d . . .
N4 N 0.39483(9) 0.2845(3) 0.52480(10) 0.0198(4) Uani 1 1 d . . .
N5 N 0.42643(10) 0.1154(3) 0.59102(10) 0.0201(4) Uani 1 1 d D . .
H5N H 0.4682(11) 0.008(3) 0.5822(12) 0.024 Uiso 1 1 d D . .
C1 C 0.36671(13) 0.6647(4) 0.15235(12) 0.0276(5) Uani 1 1 d . . .
H1A H 0.3448 0.8270 0.1326 0.041 Uiso 1 1 calc R . .
H1B H 0.3220 0.5507 0.1106 0.041 Uiso 1 1 calc R . .
H1C H 0.4329 0.6416 0.1467 0.041 Uiso 1 1 calc R . .
C2 C 0.33475(11) 0.7772(3) 0.30814(11) 0.0206(4) Uani 1 1 d . . .
H2B H 0.3082 0.9314 0.2912 0.025 Uiso 1 1 calc R . .
C3 C 0.34715(11) 0.6644(3) 0.39491(12) 0.0205(4) Uani 1 1 d . . .
H3A H 0.3308 0.7222 0.4499 0.025 Uiso 1 1 calc R . .
C4 C 0.38947(11) 0.4445(3) 0.38419(12) 0.0170(4) Uani 1 1 d . . .
C5 C 0.40592(11) 0.1354(3) 0.68000(11) 0.0182(4) Uani 1 1 d . . .
C6 C 0.43307(12) -0.0471(3) 0.74645(12) 0.0216(4) Uani 1 1 d . . .
H6A H 0.4651 -0.1838 0.7317 0.026 Uiso 1 1 calc R . .
C7 C 0.41370(12) -0.0308(4) 0.83428(12) 0.0246(5) Uani 1 1 d . . .
H7A H 0.4330 -0.1572 0.8793 0.029 Uiso 1 1 calc R . .
C8 C 0.36643(12) 0.1672(4) 0.85850(12) 0.0239(5) Uani 1 1 d . . .
C9 C 0.34001(12) 0.3475(4) 0.79108(12) 0.0240(5) Uani 1 1 d . . .
H9A H 0.3077 0.4837 0.8058 0.029 Uiso 1 1 calc R . .
C10 C 0.35912(12) 0.3360(3) 0.70262(12) 0.0227(5) Uani 1 1 d . . .
H10A H 0.3406 0.4633 0.6579 0.027 Uiso 1 1 calc R . .
C11 C 0.34517(14) 0.1840(4) 0.95438(13) 0.0358(5) Uani 1 1 d . . .
H11A H 0.3240 0.0282 0.9713 0.054 Uiso 1 1 calc R . .
H11B H 0.2932 0.3010 0.9500 0.054 Uiso 1 1 calc R . .
H11C H 0.4045 0.2335 1.0041 0.054 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 N2 112.18(13) . .
C2 N1 C1 127.57(16) . .
N2 N1 C1 120.24(14) . .
C4 N2 N1 104.38(13) . .
N4 N3 C4 110.59(14) . .
N3 N4 N5 113.66(14) . .
N4 N5 C5 119.05(14) . .
N4 N5 H5N 119.0(11) . .
C5 N5 H5N 121.1(11) . .
N1 C1 H1A 109.5 . .
N1 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
N1 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N1 C2 C3 107.11(16) . .
N1 C2 H2B 126.4 . .
C3 C2 H2B 126.4 . .
C2 C3 C4 104.52(15) . .
C2 C3 H3A 127.7 . .
C4 C3 H3A 127.7 . .
N2 C4 C3 111.81(15) . .
N2 C4 N3 116.88(15) . .
C3 C4 N3 131.26(15) . .
C6 C5 C10 119.47(16) . .
C6 C5 N5 119.20(16) . .
C10 C5 N5 121.34(16) . .
C7 C6 C5 120.10(17) . .
C7 C6 H6A 119.9 . .
C5 C6 H6A 119.9 . .
C6 C7 C8 121.61(17) . .
C6 C7 H7A 119.2 . .
C8 C7 H7A 119.2 . .
C9 C8 C7 117.33(16) . .
C9 C8 C11 121.23(18) . .
C7 C8 C11 121.44(17) . .
C8 C9 C10 122.18(17) . .
C8 C9 H9A 118.9 . .
C10 C9 H9A 118.9 . .
C9 C10 C5 119.31(17) . .
C9 C10 H10A 120.3 . .
C5 C10 H10A 120.3 . .
C8 C11 H11A 109.5 . .
C8 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C8 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.349(2) .
N1 N2 1.356(2) .
N1 C1 1.448(2) .
N2 C4 1.332(2) .
N3 N4 1.2758(18) .
N3 C4 1.408(2) .
N4 N5 1.333(2) .
N5 C5 1.407(2) .
N5 H5N 0.883(9) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.373(2) .
C2 H2B 0.9500 .
C3 C4 1.404(2) .
C3 H3A 0.9500 .
C5 C6 1.383(2) .
C5 C10 1.397(3) .
C6 C7 1.381(2) .
C6 H6A 0.9500 .
C7 C8 1.398(3) .
C7 H7A 0.9500 .
C8 C9 1.382(3) .
C8 C11 1.508(2) .
C9 C10 1.387(2) .
C9 H9A 0.9500 .
C10 H10A 0.9500 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N5 H5N N3 0.883(9) 2.290(10) 3.172(2) 176.2(16) 3_656
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C2 N1 N2 C4 0.12(17) . . . .
C1 N1 N2 C4 -178.48(13) . . . .
C4 N3 N4 N5 -178.48(13) . . . .
N3 N4 N5 C5 175.40(13) . . . .
N2 N1 C2 C3 -0.47(18) . . . .
C1 N1 C2 C3 178.00(15) . . . .
N1 C2 C3 C4 0.60(17) . . . .
N1 N2 C4 C3 0.28(17) . . . .
N1 N2 C4 N3 -177.28(13) . . . .
C2 C3 C4 N2 -0.55(18) . . . .
C2 C3 C4 N3 176.55(16) . . . .
N4 N3 C4 N2 -170.57(13) . . . .
N4 N3 C4 C3 12.4(2) . . . .
N4 N5 C5 C6 175.88(14) . . . .
N4 N5 C5 C10 -4.4(2) . . . .
C10 C5 C6 C7 0.2(2) . . . .
N5 C5 C6 C7 179.93(15) . . . .
C5 C6 C7 C8 0.2(3) . . . .
C6 C7 C8 C9 -0.3(3) . . . .
C6 C7 C8 C11 179.84(16) . . . .
C7 C8 C9 C10 -0.1(3) . . . .
C11 C8 C9 C10 179.79(15) . . . .
C8 C9 C10 C5 0.5(3) . . . .
C6 C5 C10 C9 -0.6(2) . . . .
N5 C5 C10 C9 179.72(14) . . . .
