#------------------------------------------------------------------------------
#$Date: 2017-07-25 05:23:27 +0300 (Tue, 25 Jul 2017) $
#$Revision: 199000 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/66/1546611.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_1546611
loop_
_publ_author_name
'Panda, Subhankar'
'Maity, Pradip'
'Manna, Debasis'
_publ_section_title
;
 Transition Metal, Azide, and Oxidant-Free Homo- and Heterocoupling of
 Ambiphilic Tosylhydrazones to the Regioselective Triazoles and Pyrazoles.
;
_journal_name_full               'Organic letters'
_journal_paper_doi               10.1021/acs.orglett.7b00313
_journal_year                    2017
_chemical_formula_moiety         'C14 Cl2 N3, C O'
_chemical_formula_sum            'C15 Cl2 N3 O'
_chemical_formula_weight         309.08
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   none
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 127.042(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.604(2)
_cell_length_b                   11.3027(11)
_cell_length_c                   16.5652(16)
_cell_measurement_reflns_used    3409
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.32
_cell_measurement_theta_min      2.20
_cell_volume                     3079.2(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19804
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0689
_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)+(0.0500P)²+12.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.1836
_reflns_number_gt                1823
_reflns_number_total             2785
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b00313_si_002.cif
_cod_data_source_block           SP-4C-TRZL
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        3079.2(5)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1546611
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Cl1 Cl 0.00696(9) 0.22939(12) 0.39193(11) 0.0936(5) Uani 1 1 d
Cl2 Cl 0.07488(10) 0.92674(14) 0.13342(10) 0.0978(5) Uani 1 1 d
C14 C 0.1568(2) 0.6983(4) 0.5759(3) 0.0530(10) Uani 1 1 d
C12 C 0.1204(2) 0.5827(4) 0.5311(3) 0.0513(10) Uani 1 1 d
C3 C 0.1428(3) 0.7464(4) 0.3794(3) 0.0573(11) Uani 1 1 d
C11 C 0.0454(3) 0.5772(4) 0.4352(3) 0.0624(11) Uani 1 1 d
C4 C 0.1423(2) 0.8329(4) 0.4394(3) 0.0526(10) Uani 1 1 d
C7 C 0.1590(3) 0.4785(4) 0.5837(3) 0.0568(10) Uani 1 1 d
C13 C 0.1644(2) 0.8020(4) 0.5393(3) 0.0531(10) Uani 1 1 d
C10 C 0.0100(3) 0.4679(4) 0.3915(3) 0.0675(12) Uani 1 1 d
C9 C 0.0508(3) 0.3659(4) 0.4463(4) 0.0643(12) Uani 1 1 d
C8 C 0.1243(3) 0.3688(4) 0.5419(3) 0.0621(11) Uani 1 1 d
C5 C 0.1227(3) 0.9497(4) 0.4052(3) 0.0670(12) Uani 1 1 d
C1 C 0.1023(3) 0.8919(4) 0.2526(3) 0.0658(12) Uani 1 1 d
C2 C 0.1222(3) 0.7752(4) 0.2845(3) 0.0607(11) Uani 1 1 d
C6 C 0.1028(3) 0.9799(4) 0.3109(4) 0.0736(13) Uani 1 1 d
N1 N 0.1924(2) 0.7206(3) 0.6755(2) 0.0606(9) Uani 1 1 d
N3 N 0.2035(2) 0.8822(3) 0.6167(3) 0.0628(10) Uani 1 1 d
N2 N 0.2198(2) 0.8316(3) 0.6986(3) 0.0675(10) Uani 1 1 d
O1 O 0.2141(3) 0.5913(4) 0.8267(3) 0.1093(15) Uani 1 1 d
C16 C 0.1938(4) 0.6319(6) 0.8873(4) 0.0983(19) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
N1 C14 C13 104.8(4)
N1 C14 C12 121.0(4)
C13 C14 C12 134.3(4)
C7 C12 C11 119.7(4)
C7 C12 C14 120.7(4)
C11 C12 C14 119.5(4)
C2 C3 C4 120.6(4)
C10 C11 C12 120.2(4)
C5 C4 C3 119.7(4)
C5 C4 C13 119.9(4)
C3 C4 C13 120.4(4)
C8 C7 C12 121.0(4)
N3 C13 C14 108.2(4)
N3 C13 C4 120.4(4)
C14 C13 C4 131.3(4)
C9 C10 C11 118.3(4)
C8 C9 C10 122.7(4)
C8 C9 Cl1 118.8(4)
C10 C9 Cl1 118.4(4)
C9 C8 C7 118.1(4)
C4 C5 C6 120.2(4)
C6 C1 C2 122.8(4)
C6 C1 Cl2 119.4(4)
C2 C1 Cl2 117.9(4)
C1 C2 C3 118.0(4)
C1 C6 C5 118.6(4)
N2 N1 C14 110.3(3)
N2 N3 C13 108.6(4)
N3 N2 N1 108.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C9 1.739(4)
Cl2 C1 1.740(4)
C14 N1 1.365(5)
C14 C13 1.371(6)
C14 C12 1.466(5)
C12 C7 1.394(6)
C12 C11 1.399(6)
C3 C2 1.397(6)
C3 C4 1.399(6)
C11 C10 1.395(6)
C4 C5 1.397(6)
C4 C13 1.470(6)
C7 C8 1.390(6)
C13 N3 1.367(5)
C10 C9 1.392(6)
C9 C8 1.384(6)
C5 C6 1.398(6)
C1 C6 1.382(7)
C1 C2 1.388(6)
N1 N2 1.335(5)
N3 N2 1.315(5)
O1 C16 1.378(6)
