#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:26:17 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179019 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/17/4121752.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_4121752
loop_
_publ_author_name
'Rodriguez, Rodrigo A.'
'Pan, Chung-Mao'
'Yabe, Yuki'
'Kawamata, Yu'
'Eastgate, Martin D.'
'Baran, Phil S.'
_publ_section_title
;
 Palau'chlor: A Practical and Reactive Chlorinating Reagent.
;
_journal_issue                   19
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6908
_journal_page_last               6911
_journal_paper_doi               10.1021/ja5031744
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C6 H4 Cl N3'
_chemical_formula_sum            'C6 H4 Cl N3'
_chemical_formula_weight         153.57
_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                63.815(6)
_cell_angle_beta                 70.832(6)
_cell_angle_gamma                70.159(6)
_cell_formula_units_Z            2
_cell_length_a                   6.3756(13)
_cell_length_b                   7.0803(16)
_cell_length_c                   7.9919(18)
_cell_measurement_reflns_used    2524
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.91
_cell_volume                     297.63(11)
_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 1.000
_diffrn_measured_fraction_theta_max 0.983
_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  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5117
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_T_max  0.9578
_exptl_absorpt_correction_T_min  0.8991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1407
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0331
_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)+(0.0497P)²+0.2260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0908
_reflns_number_gt                1290
_reflns_number_total             1407
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5031744_si_016.cif
_cod_data_source_block           baran356
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4121744--4121757.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4121752
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
Cl1 Cl 0.11853(6) 0.76474(6) 0.85809(5) 0.01651(15) Uani 1 1 d .
N1 N 0.4360(2) 0.7527(2) 0.54329(19) 0.0104(3) Uani 1 1 d .
N2 N 0.7702(2) 0.7004(2) 0.6139(2) 0.0146(3) Uani 1 1 d .
N3 N 0.6387(2) 0.7621(2) 0.1769(2) 0.0158(3) Uani 1 1 d .
C1 C 0.3900(3) 0.7409(3) 0.7270(2) 0.0137(3) Uani 1 1 d .
C2 C 0.5951(3) 0.7098(3) 0.7675(2) 0.0145(3) Uani 1 1 d .
H2A H 0.6134 0.6966 0.8858 0.017 Uiso 1 1 calc R
C3 C 0.6709(3) 0.7259(3) 0.4801(2) 0.0134(3) Uani 1 1 d .
C4 C 0.7642(3) 0.7289(3) 0.2932(2) 0.0147(3) Uani 1 1 d .
H4A H 0.9251 0.7059 0.2493 0.018 Uiso 1 1 calc R
C5 C 0.4075(3) 0.7912(2) 0.2428(2) 0.0121(3) Uani 1 1 d .
H5A H 0.3160 0.8177 0.1584 0.015 Uiso 1 1 calc R
C6 C 0.3002(3) 0.7842(3) 0.4253(2) 0.0141(3) Uani 1 1 d .
H6A H 0.1397 0.8003 0.4681 0.017 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0115(2) 0.0211(2) 0.0149(2) -0.00757(17) 0.00061(15) -0.00348(16)
N1 0.0083(6) 0.0106(6) 0.0112(6) -0.0039(5) -0.0012(5) -0.0021(5)
N2 0.0121(7) 0.0154(7) 0.0163(7) -0.0050(5) -0.0043(5) -0.0032(5)
N3 0.0159(7) 0.0154(7) 0.0152(7) -0.0058(6) -0.0022(6) -0.0033(6)
C1 0.0142(8) 0.0134(7) 0.0113(7) -0.0041(6) -0.0007(6) -0.0031(6)
C2 0.0165(8) 0.0138(7) 0.0140(8) -0.0058(6) -0.0044(6) -0.0024(6)
C3 0.0098(7) 0.0126(7) 0.0161(8) -0.0041(6) -0.0023(6) -0.0027(6)
C4 0.0112(8) 0.0140(7) 0.0168(8) -0.0054(6) -0.0011(6) -0.0027(6)
C5 0.0111(8) 0.0085(7) 0.0169(8) -0.0029(6) -0.0065(6) -0.0015(6)
C6 0.0115(8) 0.0138(7) 0.0173(8) -0.0054(6) -0.0044(6) -0.0024(6)
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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C6 133.21(15)
C1 N1 C3 105.91(14)
C6 N1 C3 120.88(14)
C3 N2 C2 105.04(15)
C4 N3 C5 118.06(14)
N1 C1 C2 106.71(15)
N1 C1 Cl1 120.99(13)
C2 C1 Cl1 132.30(14)
N2 C2 C1 110.70(15)
N2 C2 H2A 124.7
C1 C2 H2A 124.7
N2 C3 N1 111.63(15)
N2 C3 C4 130.92(16)
N1 C3 C4 117.44(15)
N3 C4 C3 122.93(16)
N3 C4 H4A 118.5
C3 C4 H4A 118.5
N3 C5 C6 123.45(15)
N3 C5 H5A 118.3
C6 C5 H5A 118.3
C5 C6 N1 117.19(15)
C5 C6 H6A 121.4
N1 C6 H6A 121.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.6997(17)
N1 C1 1.369(2)
N1 C6 1.381(2)
N1 C3 1.389(2)
N2 C3 1.331(2)
N2 C2 1.371(2)
N3 C4 1.315(2)
N3 C5 1.369(2)
C1 C2 1.372(2)
C2 H2A 0.9500
C3 C4 1.408(2)
C4 H4A 0.9500
C5 C6 1.379(2)
C5 H5A 0.9500
C6 H6A 0.9500
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
C6 N1 C1 C2 -179.26(16)
C3 N1 C1 C2 0.50(18)
C6 N1 C1 Cl1 0.6(3)
C3 N1 C1 Cl1 -179.65(11)
C3 N2 C2 C1 0.01(19)
N1 C1 C2 N2 -0.33(19)
Cl1 C1 C2 N2 179.85(13)
C2 N2 C3 N1 0.32(18)
C2 N2 C3 C4 -179.44(17)
C1 N1 C3 N2 -0.52(18)
C6 N1 C3 N2 179.27(14)
C1 N1 C3 C4 179.27(14)
C6 N1 C3 C4 -0.9(2)
C5 N3 C4 C3 -1.2(2)
N2 C3 C4 N3 -178.14(17)
N1 C3 C4 N3 2.1(2)
C4 N3 C5 C6 -1.0(2)
N3 C5 C6 N1 2.1(2)
C1 N1 C6 C5 178.69(16)
C3 N1 C6 C5 -1.0(2)
