#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/78/1517829.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_1517829
loop_
_publ_author_name
'Cai, Zhong-Jian'
'Lu, Xin-Mou'
'Zi, You'
'Yang, Chao'
'Shen, Ling-Jie'
'Li, Jian'
'Wang, Shun-Yi'
'Ji, Shun-Jun'
_publ_section_title
;
 I2/TBPB Mediated Oxidative Reaction of N-Tosylhydrazones with Anilines:
 Practical Construction of 1,4-Disubstituted 1,2,3-Triazoles under
 Metal-Free and Azide-Free Conditions.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5108
_journal_page_last               5111
_journal_paper_doi               10.1021/ol502431b
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H15 N3'
_chemical_formula_sum            'C20 H15 N3'
_chemical_formula_weight         297.35
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9901(2)
_cell_length_b                   12.9361(3)
_cell_length_c                   15.1823(4)
_cell_measurement_reflns_used    6497
_cell_measurement_temperature    296.7(9)
_cell_measurement_theta_max      29.0990
_cell_measurement_theta_min      4.1220
_cell_volume                     1569.25(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      296.7(9)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0809270000
_diffrn_orient_matrix_UB_12      -0.0194085000
_diffrn_orient_matrix_UB_13      -0.0097797000
_diffrn_orient_matrix_UB_21      0.0012852000
_diffrn_orient_matrix_UB_22      -0.0294438000
_diffrn_orient_matrix_UB_23      0.0393996000
_diffrn_orient_matrix_UB_31      -0.0365106000
_diffrn_orient_matrix_UB_32      0.0419782000
_diffrn_orient_matrix_UB_33      0.0231134000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15281
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.00
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(5)
_refine_ls_extinction_coef       0.028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0692
_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)+(0.0884P)²+1.0816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1871
_refine_ls_wR_factor_ref         0.1905
_reflns_number_gt                2987
_reflns_number_total             3185
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502431b_si_002.cif
_cod_data_source_block           g140304b
_cod_depositor_comments
'Adding full bibliography for 1517829--1517830.cif.'
_cod_original_cell_volume        1569.26(7)
_cod_database_code               1517829
#BEGIN Tags that were not found in dictionaries:
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C2) = Uanis(C3) = Uanis(C4) = Uanis(C5) = Uanis(C6)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -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_calc_flag
_atom_site_refinement_flags_posn
N1 N -0.8093(3) -0.49663(18) -0.46265(16) 0.0443(6) Uani 1 d .
N2 N -0.9209(4) -0.5003(2) -0.39547(19) 0.0576(7) Uani 1 d .
N3 N -0.9506(4) -0.4046(2) -0.37193(19) 0.0571(7) Uani 1 d .
C1 C -0.6808(5) -0.7475(4) -0.3123(2) 0.0743(5) Uani 1 d .
H1 H -0.7466 -0.8011 -0.3340 0.089 Uiso 1 calc R
C2 C -0.6278(5) -0.7499(4) -0.2248(2) 0.0743(5) Uani 1 d .
H2 H -0.6576 -0.8048 -0.1885 0.089 Uiso 1 calc R
C3 C -0.5325(5) -0.6717(4) -0.1933(3) 0.0743(5) Uani 1 d .
H3 H -0.4971 -0.6734 -0.1350 0.089 Uiso 1 calc R
C4 C -0.4881(5) -0.5914(4) -0.2446(3) 0.0743(5) Uani 1 d .
H4 H -0.4219 -0.5387 -0.2217 0.089 Uiso 1 calc R
C5 C -0.5413(5) -0.5871(4) -0.3324(3) 0.0743(5) Uani 1 d .
H5 H -0.5123 -0.5308 -0.3674 0.089 Uiso 1 calc R
C6 C -0.6374(5) -0.6669(4) -0.3675(3) 0.0743(5) Uani 1 d .
C7 C -0.6815(4) -0.6704(2) -0.4624(2) 0.0457(7) Uani 1 d .
C8 C -0.6403(5) -0.7582(3) -0.5115(2) 0.0538(8) Uani 1 d .
H8 H -0.5914 -0.8145 -0.4833 0.065 Uiso 1 calc R
C9 C -0.6707(5) -0.7633(3) -0.6008(2) 0.0581(8) Uani 1 d .
H9 H -0.6419 -0.8226 -0.6318 0.070 Uiso 1 calc R
C10 C -0.7432(5) -0.6813(3) -0.6446(2) 0.0576(8) Uani 1 d .
H10 H -0.7614 -0.6845 -0.7051 0.069 Uiso 1 calc R
C11 C -0.7882(4) -0.5948(3) -0.5978(2) 0.0525(7) Uani 1 d .
H11 H -0.8395 -0.5398 -0.6264 0.063 Uiso 1 calc R
C12 C -0.7574(4) -0.5892(2) -0.5080(2) 0.0453(7) Uani 1 d .
C13 C -0.7685(4) -0.3985(2) -0.4809(2) 0.0464(7) Uani 1 d .
H13 H -0.6946 -0.3754 -0.5240 0.056 Uiso 1 calc R
C14 C -0.8579(4) -0.3396(2) -0.42341(18) 0.0429(6) Uani 1 d .
C15 C -0.8677(4) -0.2261(2) -0.41469(19) 0.0456(7) Uani 1 d .
C16 C -0.7950(4) -0.1617(2) -0.4776(2) 0.0544(8) Uani 1 d .
H16 H -0.7394 -0.1907 -0.5254 0.065 Uiso 1 calc R
C17 C -0.8044(5) -0.0560(3) -0.4699(3) 0.0678(10) Uani 1 d .
H17 H -0.7550 -0.0140 -0.5123 0.081 Uiso 1 calc R
C18 C -0.8870(5) -0.0121(3) -0.3996(3) 0.0749(12) Uani 1 d .
H18 H -0.8947 0.0595 -0.3949 0.090 Uiso 1 calc R
C19 C -0.9581(5) -0.0746(3) -0.3360(3) 0.0709(11) Uani 1 d .
H19 H -1.0123 -0.0448 -0.2881 0.085 Uiso 1 calc R
C20 C -0.9496(4) -0.1815(3) -0.3431(2) 0.0576(8) Uani 1 d .
H20 H -0.9982 -0.2231 -0.3002 0.069 Uiso 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 C12 121.3(2)
C13 N1 N2 110.4(2)
C13 N1 C12 128.2(3)
N3 N2 N1 106.9(2)
N2 N3 C14 109.1(2)
C6 C1 C2 121.2(4)
C3 C2 C1 119.4(5)
C4 C3 C2 121.4(4)
C3 C4 C5 120.1(4)
C6 C5 C4 120.1(5)
C1 C6 C5 117.8(4)
C1 C6 C7 120.4(4)
C5 C6 C7 121.7(4)
C8 C7 C6 119.1(3)
C12 C7 C6 124.1(3)
C12 C7 C8 116.7(3)
C9 C8 C7 121.4(3)
C8 C9 C10 120.8(3)
C11 C10 C9 119.1(3)
C10 C11 C12 120.4(3)
C7 C12 N1 120.9(3)
C11 C12 N1 117.5(3)
C11 C12 C7 121.6(3)
N1 C13 C14 105.7(3)
N3 C14 C15 122.1(3)
C13 C14 N3 107.9(3)
C13 C14 C15 129.9(3)
C16 C15 C14 120.7(3)
C16 C15 C20 118.9(3)
C20 C15 C14 120.4(3)
C17 C16 C15 120.9(4)
C16 C17 C18 120.1(4)
C17 C18 C19 119.8(3)
C18 C19 C20 120.6(4)
C19 C20 C15 119.7(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.356(4)
N1 C12 1.442(4)
N1 C13 1.339(4)
N2 N3 1.310(4)
N3 C14 1.366(4)
C1 C2 1.395(5)
C1 C6 1.382(6)
C2 C3 1.354(6)
C3 C4 1.346(6)
C4 C5 1.401(5)
C5 C6 1.392(6)
C6 C7 1.484(5)
C7 C8 1.398(4)
C7 C12 1.397(4)
C8 C9 1.379(5)
C9 C10 1.380(5)
C10 C11 1.373(5)
C11 C12 1.388(4)
C13 C14 1.361(4)
C14 C15 1.477(4)
C15 C16 1.393(5)
C15 C20 1.394(4)
C16 C17 1.375(5)
C17 C18 1.378(6)
C18 C19 1.382(6)
C19 C20 1.389(5)
