#------------------------------------------------------------------------------
#$Date: 2019-11-11 17:39:14 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226755 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/52/4035291.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_4035291
loop_
_publ_author_name
'Pathare, Ramdas S.'
'Ansari, Arshad J.'
'Verma, Sarika'
'Maurya, Anand'
'Maurya, Antim K.'
'Agnihotri, Vijai K.'
'Sharon, Ashoke'
'Pardasani, Ram T.'
'Sawant, Devesh M.'
_publ_section_title
;
 Sequential Pd(0)/Fe(III) Catalyzed Azide-Isocyanide Coupling/Cyclization
 Reaction: One-Pot Synthesis of Aminotetrazoles.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9530
_journal_page_last               9537
_journal_paper_doi               10.1021/acs.joc.8b01261
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C12 H14 N6'
_chemical_formula_sum            'C12 H14 N6'
_chemical_formula_weight         242.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-10-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.424(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5723(5)
_cell_length_b                   7.0541(4)
_cell_length_c                   10.5423(5)
_cell_measurement_reflns_used    1344
_cell_measurement_temperature    298.2
_cell_measurement_theta_max      25.0800
_cell_measurement_theta_min      2.7570
_cell_volume                     620.07(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.2
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -69.00 118.80   0.30   10.00    --   29.89  54.00 -60.00  626
  2  ω    -69.00 118.80   0.30   10.00    --   29.89  54.00-150.00  626
  3  ω    -69.00  36.00   0.30   10.00    --   29.89  54.00  90.00  350
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0636378000
_diffrn_orient_matrix_UB_12      0.0189719000
_diffrn_orient_matrix_UB_13      0.0548511000
_diffrn_orient_matrix_UB_21      -0.0443523000
_diffrn_orient_matrix_UB_22      -0.0428028000
_diffrn_orient_matrix_UB_23      0.0413523000
_diffrn_orient_matrix_UB_31      0.0349197000
_diffrn_orient_matrix_UB_32      -0.0889965000
_diffrn_orient_matrix_UB_33      -0.0081874000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7656
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.800
_diffrn_reflns_theta_min         2.768
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       needle
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.012(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2287
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0708
_refine_ls_shift/su_max          0.735
_refine_ls_shift/su_mean         0.013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1396P)²+0.0423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1991
_refine_ls_wR_factor_ref         0.2566
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1259
_reflns_number_total             2287
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b01261_si_002.cif
_cod_data_source_block           rmo-107-2
_cod_original_cell_volume        620.08(6)
_cod_database_code               4035291
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H11A(0.5) H11B(0.5) H11C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.062
_oxdiff_exptl_absorpt_empirical_full_min 0.951
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5988(2) 0.2500 0.31537(17) 0.0529(5) Uani 1 2 d S T P . .
H1 H 0.7014 0.2500 0.3434 0.063 Uiso 1 2 calc RS T P . .
N2 N 0.6411(2) 0.2500 0.09918(16) 0.0501(5) Uani 1 2 d S T P . .
N3 N 0.5451(3) 0.2500 -0.02318(18) 0.0660(6) Uani 1 2 d S T P . .
N4 N 0.3999(3) 0.2500 -0.0108(2) 0.0725(7) Uani 1 2 d S T P . .
N5 N 0.3915(3) 0.2500 0.1175(2) 0.0643(6) Uani 1 2 d S T P . .
N6 N 0.9048(3) 0.2500 0.5842(3) 0.0790(7) Uani 1 2 d S T P . .
C1 C 0.5098(3) 0.2500 0.4108(2) 0.0470(5) Uani 1 2 d S T P . .
C2 C 0.5971(3) 0.2500 0.5421(2) 0.0497(5) Uani 1 2 d S T P . .
C3 C 0.5162(4) 0.2500 0.6426(2) 0.0627(7) Uani 1 2 d S T P . .
H3 H 0.5744 0.2500 0.7289 0.075 Uiso 1 2 calc RS T P . .
C4 C 0.3526(4) 0.2500 0.6160(3) 0.0716(8) Uani 1 2 d S T P . .
H4 H 0.2991 0.2500 0.6834 0.086 Uiso 1 2 calc RS T P . .
C5 C 0.2676(4) 0.2500 0.4874(3) 0.0712(8) Uani 1 2 d S T P . .
H5 H 0.1561 0.2500 0.4690 0.085 Uiso 1 2 calc RS T P . .
C6 C 0.3440(3) 0.2500 0.3852(3) 0.0603(6) Uani 1 2 d S T P . .
H6 H 0.2840 0.2500 0.2996 0.072 Uiso 1 2 calc RS T P . .
C7 C 0.7681(3) 0.2500 0.5692(2) 0.0561(6) Uani 1 2 d S T P . .
C8 C 0.5431(3) 0.2500 0.1834(2) 0.0492(5) Uani 1 2 d S T P . .
C9 C 0.8209(3) 0.2500 0.1219(2) 0.0538(6) Uani 1 2 d S T P . .
C11 C 0.8618(4) 0.2500 -0.0115(3) 0.0785(8) Uani 1 2 d S T P . .
H11A H 0.9748 0.2706 -0.0008 0.118 Uiso 0.5 1 calc GR . . A -1
H11B H 0.8035 0.3494 -0.0642 0.118 Uiso 0.5 1 calc GR . . A -1
H11C H 0.8329 0.1300 -0.0533 0.118 Uiso 0.5 1 calc GR . . A -1
C12 C 0.8870(2) 0.4289(2) 0.19609(19) 0.0635(5) Uani 1 1 d . . . . .
H12A H 0.8379 0.5382 0.1489 0.095 Uiso 1 1 calc GR . . . .
H12B H 1.0010 0.4343 0.2052 0.095 Uiso 1 1 calc GR . . . .
H12C H 0.8638 0.4269 0.2809 0.095 Uiso 1 1 calc GR . . . .
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
C1 N1 H1 116.0 . .
C8 N1 H1 116.0 . .
C8 N1 C1 128.0(2) . .
N3 N2 C9 121.59(18) . .
C8 N2 N3 106.9(2) . .
C8 N2 C9 131.52(18) . .
N4 N3 N2 107.0(2) . .
N3 N4 N5 112.0(2) . .
C8 N5 N4 104.4(2) . .
N1 C1 C2 116.9(2) . .
C6 C1 N1 124.6(2) . .
C6 C1 C2 118.5(2) . .
C1 C2 C7 118.81(19) . .
C3 C2 C1 120.1(2) . .
C3 C2 C7 121.1(2) . .
C2 C3 H3 119.6 . .
C4 C3 C2 120.8(3) . .
C4 C3 H3 119.6 . .
C3 C4 H4 120.5 . .
C3 C4 C5 118.9(2) . .
C5 C4 H4 120.5 . .
C4 C5 H5 119.1 . .
C4 C5 C6 121.8(3) . .
C6 C5 H5 119.1 . .
C1 C6 C5 119.9(3) . .
C1 C6 H6 120.0 . .
C5 C6 H6 120.0 . .
N6 C7 C2 176.5(2) . .
N2 C8 N1 123.0(2) . .
N5 C8 N1 127.2(2) . .
N5 C8 N2 109.8(2) . .
N2 C9 C11 107.4(2) . .
N2 C9 C12 109.12(12) . .
N2 C9 C12 109.12(12) . 4_565
C12 C9 C11 109.58(13) . .
C12 C9 C11 109.58(13) 4_565 .
C12 C9 C12 111.9(2) . 4_565
C9 C11 H11A 109.7 . .
C9 C11 H11B 109.6 . .
C9 C11 H11C 109.6 . .
H11A C11 H11B 109.3 . .
H11A C11 H11C 109.3 . .
H11B C11 H11C 109.3 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 H1 0.8600 .
N1 C1 1.397(3) .
N1 C8 1.362(3) .
N2 N3 1.360(3) .
N2 C8 1.357(3) .
N2 C9 1.504(3) .
N3 N4 1.280(3) .
N4 N5 1.372(3) .
N5 C8 1.323(3) .
N6 C7 1.146(3) .
C1 C2 1.412(3) .
C1 C6 1.384(3) .
C2 C3 1.395(3) .
C2 C7 1.427(3) .
C3 H3 0.9300 .
C3 C4 1.365(4) .
C4 H4 0.9300 .
C4 C5 1.382(5) .
C5 H5 0.9300 .
C5 C6 1.384(3) .
C6 H6 0.9300 .
C9 C11 1.527(3) .
C9 C12 1.523(2) .
C9 C12 1.523(2) 4_565
C11 H11A 0.9618 .
C11 H11B 0.9618 .
C11 H11C 0.9618 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
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_4
N1 C1 C2 C3 180.000(1) .
N1 C1 C2 C7 0.000(1) .
N1 C1 C6 C5 180.000(1) .
N2 N3 N4 N5 0.000(0) .
N3 N2 C8 N1 180.000(0) .
N3 N2 C8 N5 0.000(0) .
N3 N2 C9 C11 0.000(0) .
N3 N2 C9 C12 118.71(12) .
N3 N2 C9 C12 -118.71(12) 4_565
N3 N4 N5 C8 0.0 .
N4 N5 C8 N1 180.000(0) .
N4 N5 C8 N2 0.000(0) .
C1 N1 C8 N2 180.000(0) .
C1 N1 C8 N5 0.000(0) .
C1 C2 C3 C4 0.000(1) .
C2 C1 C6 C5 0.000(1) .
C2 C3 C4 C5 0.000(1) .
C3 C4 C5 C6 0.000(1) .
C4 C5 C6 C1 0.000(1) .
C6 C1 C2 C3 0.000(1) .
C6 C1 C2 C7 180.000(1) .
C7 C2 C3 C4 180.000(1) .
C8 N1 C1 C2 180.000(0) .
C8 N1 C1 C6 0.000(1) .
C8 N2 N3 N4 0.0 .
C8 N2 C9 C11 180.000(0) .
C8 N2 C9 C12 61.29(12) 4_565
C8 N2 C9 C12 -61.29(12) .
C9 N2 N3 N4 180.0 .
C9 N2 C8 N1 0.000(0) .
C9 N2 C8 N5 180.000(0) .
