#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:26:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178469 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/90/4029009.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_4029009
loop_
_publ_author_name
'Nasr-Esfahani, Mahboobeh'
'Mohammadpoor-Baltork, Iraj'
'Khosropour, Ahmad R.'
'Moghadam, Majid'
'Mirkhani, Valiollah'
'Tangestaninejad, Shahram'
'Amiri Rudbari, Hadi'
_publ_section_title
;
 Copper Immobilized on Nanosilica Triazine Dendrimer
 (Cu(II)-TD@nSiO2)-Catalyzed Regioselective Synthesis of 1,4-Disubstituted
 1,2,3-Triazoles and Bis- and Tris-Triazoles via a One-Pot Multicomponent
 Click Reaction.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1437
_journal_paper_doi               10.1021/jo402170n
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C17 H17 N3'
_chemical_formula_sum            'C17 H17 N3'
_chemical_formula_weight         263.34
_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                104.534(11)
_cell_angle_beta                 98.370(12)
_cell_angle_gamma                93.921(12)
_cell_formula_units_Z            2
_cell_length_a                   5.6469(8)
_cell_length_b                   9.0685(12)
_cell_length_c                   14.814(2)
_cell_measurement_temperature    298(2)
_cell_volume                     722.14(18)
_computing_cell_refinement       'X-Area 1.52'
_computing_data_collection       'X-Area 1.52 (Stoe & Cie GmbH, 2007)'
_computing_data_reduction        'X-Area 1.52'
_computing_molecular_graphics    'XPW (Siemens, 1996)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.793
_diffrn_measured_fraction_theta_max 0.793
_diffrn_measurement_device_type  'STOE IPDS 2T Image Plate diffractometer'
_diffrn_measurement_method       'ω 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  0.0699
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5065
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         3.67
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2118
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0783
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0644P)²+0.9928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1917
_refine_ls_wR_factor_ref         0.2092
_reflns_number_gt                1458
_reflns_number_total             2118
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo402170n_si_002.cif
_cod_data_source_block           t+p-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        722.13(17)
_cod_database_code               4029009
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 0.8469(6) 0.3064(4) 0.6787(2) 0.0402(8) Uani 1 1 d .
C10 C 0.6427(8) 0.0406(5) 0.6259(2) 0.0398(10) Uani 1 1 d .
C11 C 0.7571(8) -0.0828(5) 0.5870(3) 0.0479(11) Uani 1 1 d .
H11 H 0.8634 -0.0727 0.5460 0.058 Uiso 1 1 calc R
N2 N 1.0843(7) 0.3114(4) 0.6827(3) 0.0539(10) Uani 1 1 d .
C15 C 0.4851(8) 0.0255(5) 0.6881(3) 0.0465(11) Uani 1 1 d .
H15 H 0.4071 0.1090 0.7143 0.056 Uiso 1 1 calc R
N3 N 1.1802(7) 0.4181(5) 0.7615(3) 0.0568(11) Uani 1 1 d .
C6 C 1.0454(7) 0.5987(5) 0.8951(3) 0.0421(10) Uani 1 1 d .
C7 C 1.0008(7) 0.4775(5) 0.8059(3) 0.0398(10) Uani 1 1 d .
C14 C 0.4423(8) -0.1108(5) 0.7117(3) 0.0472(11) Uani 1 1 d .
C13 C 0.5577(8) -0.2343(5) 0.6704(3) 0.0493(12) Uani 1 1 d .
H13 H 0.5282 -0.3273 0.6847 0.059 Uiso 1 1 calc R
C12 C 0.7166(8) -0.2232(5) 0.6080(3) 0.0501(12) Uani 1 1 d .
C8 C 0.7871(7) 0.4069(5) 0.7524(3) 0.0389(10) Uani 1 1 d .
H8 H 0.6331 0.4247 0.7646 0.047 Uiso 1 1 calc R
C9 C 0.6859(8) 0.1924(5) 0.6027(3) 0.0515(12) Uani 1 1 d .
H9A H 0.7552 0.1760 0.5453 0.062 Uiso 1 1 calc R
H9B H 0.5327 0.2323 0.5908 0.062 Uiso 1 1 calc R
C5 C 1.2574(8) 0.6144(5) 0.9578(3) 0.0539(12) Uani 1 1 d .
H5 H 1.3734 0.5486 0.9425 0.065 Uiso 1 1 calc R
C1 C 0.8780(9) 0.6977(6) 0.9200(3) 0.0579(13) Uani 1 1 d .
H1 H 0.7337 0.6891 0.8788 0.069 Uiso 1 1 calc R
C17 C 0.8387(11) -0.3581(6) 0.5621(4) 0.0784(17) Uani 1 1 d .
H17A H 0.7458 -0.4095 0.5013 0.118 Uiso 1 1 calc R
H17B H 0.8511 -0.4279 0.6013 0.118 Uiso 1 1 calc R
H17C H 0.9968 -0.3230 0.5544 0.118 Uiso 1 1 calc R
C4 C 1.3005(10) 0.7260(6) 1.0428(3) 0.0672(15) Uani 1 1 d .
H4 H 1.4445 0.7349 1.0843 0.081 Uiso 1 1 calc R
C16 C 0.2787(10) -0.1245(6) 0.7817(4) 0.0742(16) Uani 1 1 d .
H16A H 0.3683 -0.0893 0.8448 0.111 Uiso 1 1 calc R
H16B H 0.2152 -0.2297 0.7701 0.111 Uiso 1 1 calc R
H16C H 0.1486 -0.0633 0.7748 0.111 Uiso 1 1 calc R
C2 C 0.9197(10) 0.8100(6) 1.0050(4) 0.0703(15) Uani 1 1 d .
H2 H 0.8042 0.8761 1.0205 0.084 Uiso 1 1 calc R
C3 C 1.1313(11) 0.8234(6) 1.0660(4) 0.0720(16) Uani 1 1 d .
H3 H 1.1601 0.8987 1.1232 0.086 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
N2 N1 C8 112.0(3)
N2 N1 C9 120.1(3)
C8 N1 C9 127.8(3)
C11 C10 C15 119.3(4)
C11 C10 C9 121.1(4)
C15 C10 C9 119.6(4)
C10 C11 C12 121.1(4)
C10 C11 H11 119.4
C12 C11 H11 119.4
N1 N2 N3 106.0(3)
C14 C15 C10 121.4(4)
C14 C15 H15 119.3
C10 C15 H15 119.3
N2 N3 C7 109.1(4)
C1 C6 C5 117.9(4)
C1 C6 C7 121.7(4)
C5 C6 C7 120.4(4)
N3 C7 C8 107.9(4)
N3 C7 C6 123.0(4)
C8 C7 C6 129.1(4)
C15 C14 C13 118.1(4)
C15 C14 C16 121.1(4)
C13 C14 C16 120.8(4)
C14 C13 C12 122.0(4)
C14 C13 H13 119.0
C12 C13 H13 119.0
C13 C12 C11 118.0(4)
C13 C12 C17 121.9(4)
C11 C12 C17 120.1(4)
N1 C8 C7 105.0(4)
N1 C8 H8 127.5
C7 C8 H8 127.5
N1 C9 C10 112.9(3)
N1 C9 H9A 109.0
C10 C9 H9A 109.0
N1 C9 H9B 109.0
C10 C9 H9B 109.0
H9A C9 H9B 107.8
C6 C5 C4 121.2(5)
C6 C5 H5 119.4
C4 C5 H5 119.4
C6 C1 C2 121.4(5)
C6 C1 H1 119.3
C2 C1 H1 119.3
C12 C17 H17A 109.5
C12 C17 H17B 109.5
H17A C17 H17B 109.5
C12 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C3 C4 C5 119.9(5)
C3 C4 H4 120.0
C5 C4 H4 120.0
C14 C16 H16A 109.5
C14 C16 H16B 109.5
H16A C16 H16B 109.5
C14 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C3 C2 C1 119.8(5)
C3 C2 H2 120.1
C1 C2 H2 120.1
C2 C3 C4 119.9(5)
C2 C3 H3 120.0
C4 C3 H3 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.331(5)
N1 C8 1.336(5)
N1 C9 1.467(5)
C10 C11 1.373(6)
C10 C15 1.395(6)
C10 C9 1.513(6)
C11 C12 1.397(6)
C11 H11 0.9300
N2 N3 1.330(5)
C15 C14 1.381(6)
C15 H15 0.9300
N3 C7 1.356(5)
C6 C1 1.373(6)
C6 C5 1.379(6)
C6 C7 1.468(6)
C7 C8 1.362(5)
C14 C13 1.388(6)
C14 C16 1.507(6)
C13 C12 1.395(6)
C13 H13 0.9300
C12 C17 1.506(6)
C8 H8 0.9300
C9 H9A 0.9700
C9 H9B 0.9700
C5 C4 1.381(6)
C5 H5 0.9300
C1 C2 1.384(6)
C1 H1 0.9300
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C4 C3 1.368(7)
C4 H4 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C2 C3 1.368(7)
C2 H2 0.9300
C3 H3 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
C15 C10 C11 C12 0.6(6)
C9 C10 C11 C12 -179.7(4)
C8 N1 N2 N3 0.1(4)
C9 N1 N2 N3 -176.1(3)
C11 C10 C15 C14 0.2(6)
C9 C10 C15 C14 -179.5(4)
N1 N2 N3 C7 0.5(5)
N2 N3 C7 C8 -0.8(5)
N2 N3 C7 C6 -179.8(4)
C1 C6 C7 N3 153.9(4)
C5 C6 C7 N3 -27.4(6)
C1 C6 C7 C8 -24.8(7)
C5 C6 C7 C8 153.9(4)
C10 C15 C14 C13 -1.1(6)
C10 C15 C14 C16 177.8(4)
C15 C14 C13 C12 1.2(6)
C16 C14 C13 C12 -177.7(4)
C14 C13 C12 C11 -0.4(6)
C14 C13 C12 C17 -179.0(4)
C10 C11 C12 C13 -0.5(6)
C10 C11 C12 C17 178.1(4)
N2 N1 C8 C7 -0.6(4)
C9 N1 C8 C7 175.2(4)
N3 C7 C8 N1 0.8(4)
C6 C7 C8 N1 179.7(4)
N2 N1 C9 C10 86.3(5)
C8 N1 C9 C10 -89.1(5)
C11 C10 C9 N1 -102.9(4)
C15 C10 C9 N1 76.8(5)
C1 C6 C5 C4 -0.1(7)
C7 C6 C5 C4 -178.8(4)
C5 C6 C1 C2 0.1(7)
C7 C6 C1 C2 178.8(4)
C6 C5 C4 C3 0.0(8)
C6 C1 C2 C3 -0.1(8)
C1 C2 C3 C4 0.0(8)
C5 C4 C3 C2 0.0(8)
