#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:26:17 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179019 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/17/4121749.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_4121749
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         'C8 H6 Cl2 N2'
_chemical_formula_sum            'C8 H6 Cl2 N2'
_chemical_formula_weight         201.05
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   21.149(4)
_cell_length_b                   40.631(8)
_cell_length_c                   3.8885(7)
_cell_measurement_reflns_used    710
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.19
_cell_measurement_theta_min      2.78
_cell_volume                     3341.4(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 0.994
_diffrn_measured_fraction_theta_max 0.975
_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  0.0854
_diffrn_reflns_av_sigmaI/netI    0.0748
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            1670
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.68
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_T_max  0.9652
_exptl_absorpt_correction_T_min  0.8143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.51(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1654
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0497
_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)+(0.0845P)²+5.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1317
_reflns_number_gt                1517
_reflns_number_total             1654
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5031744_si_002.cif
_cod_data_source_block           baran406
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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      Fdd2
_cod_database_code               4121749
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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 0.04087(4) 0.05038(2) 0.4642(2) 0.0198(3) Uani 1 1 d .
Cl2 Cl -0.17834(4) -0.01413(2) 1.1934(3) 0.0195(3) Uani 1 1 d .
N1 N -0.08097(15) 0.11272(7) 0.7440(10) 0.0206(8) Uani 1 1 d .
N2 N -0.02532(15) 0.10430(7) 0.5957(9) 0.0189(7) Uani 1 1 d .
C1 C -0.02224(17) 0.07193(8) 0.6258(10) 0.0152(8) Uani 1 1 d .
C2 C -0.07542(17) 0.05825(9) 0.7956(10) 0.0143(8) Uani 1 1 d .
C3 C -0.09493(17) 0.02664(9) 0.8909(10) 0.0167(8) Uani 1 1 d .
H3A H -0.0701 0.0077 0.8429 0.020 Uiso 1 1 calc R
C4 C -0.15192(17) 0.02451(8) 1.0576(10) 0.0165(8) Uani 1 1 d .
C5 C -0.19036(18) 0.05209(9) 1.1341(11) 0.0177(8) Uani 1 1 d .
H5A H -0.2295 0.0491 1.2500 0.021 Uiso 1 1 calc R
C6 C -0.17106(17) 0.08328(9) 1.0406(11) 0.0178(9) Uani 1 1 d .
H6A H -0.1962 0.1021 1.0895 0.021 Uiso 1 1 calc R
C7 C -0.11279(17) 0.08603(9) 0.8704(10) 0.0168(8) Uani 1 1 d .
C8 C -0.0982(2) 0.14715(9) 0.7793(11) 0.0265(10) Uani 1 1 d .
H8A H -0.0842 0.1593 0.5755 0.040 Uiso 1 1 calc R
H8B H -0.0778 0.1563 0.9844 0.040 Uiso 1 1 calc R
H8C H -0.1442 0.1490 0.8019 0.040 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 0.0162(5) 0.0224(4) 0.0210(5) 0.0019(4) 0.0045(4) 0.0016(3)
Cl2 0.0173(5) 0.0205(4) 0.0205(5) 0.0034(4) -0.0011(4) -0.0036(3)
N1 0.0207(16) 0.0160(14) 0.025(2) -0.0014(14) 0.0036(16) 0.0010(12)
N2 0.0185(16) 0.0215(15) 0.0167(17) -0.0010(13) 0.0033(15) -0.0020(13)
C1 0.0162(18) 0.0188(16) 0.010(2) 0.0024(15) -0.0011(16) 0.0009(14)
C2 0.0135(17) 0.0185(17) 0.0110(19) -0.0025(14) -0.0012(15) -0.0002(13)
C3 0.0147(17) 0.0181(16) 0.017(2) -0.0007(16) -0.0013(17) 0.0007(14)
C4 0.0176(19) 0.0169(17) 0.0150(19) 0.0018(15) -0.0065(16) -0.0006(14)
C5 0.0110(17) 0.0271(19) 0.015(2) -0.0008(17) 0.0004(17) -0.0003(13)
C6 0.0150(18) 0.0204(18) 0.018(2) -0.0021(15) -0.0027(16) 0.0027(13)
C7 0.0169(17) 0.0175(16) 0.016(2) -0.0049(15) -0.0049(17) 0.0024(13)
C8 0.038(2) 0.0156(18) 0.026(3) -0.0007(16) 0.003(2) 0.0048(16)
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
N2 N1 C7 112.4(3)
N2 N1 C8 120.1(3)
C7 N1 C8 127.3(3)
C1 N2 N1 104.9(3)
N2 C1 C2 113.1(3)
N2 C1 Cl1 120.9(3)
C2 C1 Cl1 126.0(3)
C3 C2 C7 121.0(4)
C3 C2 C1 135.8(3)
C7 C2 C1 103.1(3)
C4 C3 C2 116.3(3)
C4 C3 H3A 121.9
C2 C3 H3A 121.9
C3 C4 C5 123.7(3)
C3 C4 Cl2 118.7(3)
C5 C4 Cl2 117.6(3)
C6 C5 C4 120.1(4)
C6 C5 H5A 120.0
C4 C5 H5A 120.0
C5 C6 C7 117.2(3)
C5 C6 H6A 121.4
C7 C6 H6A 121.4
N1 C7 C6 131.7(3)
N1 C7 C2 106.6(3)
C6 C7 C2 121.8(3)
N1 C8 H8A 109.5
N1 C8 H8B 109.5
H8A C8 H8B 109.5
N1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.715(4)
Cl2 C4 1.748(4)
N1 N2 1.354(4)
N1 C7 1.368(5)
N1 C8 1.452(5)
N2 C1 1.322(4)
C1 C2 1.418(5)
C2 C3 1.399(5)
C2 C7 1.408(5)
C3 C4 1.371(5)
C3 H3A 0.9500
C4 C5 1.416(5)
C5 C6 1.380(5)
C5 H5A 0.9500
C6 C7 1.403(5)
C6 H6A 0.9500
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
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
C7 N1 N2 C1 0.6(4)
C8 N1 N2 C1 175.7(3)
N1 N2 C1 C2 -0.3(4)
N1 N2 C1 Cl1 179.0(3)
N2 C1 C2 C3 -179.8(4)
Cl1 C1 C2 C3 1.0(7)
N2 C1 C2 C7 -0.1(4)
Cl1 C1 C2 C7 -179.3(3)
C7 C2 C3 C4 0.3(6)
C1 C2 C3 C4 180.0(4)
C2 C3 C4 C5 0.0(6)
C2 C3 C4 Cl2 -178.5(3)
C3 C4 C5 C6 -0.1(6)
Cl2 C4 C5 C6 178.4(3)
C4 C5 C6 C7 0.0(6)
N2 N1 C7 C6 -179.9(4)
C8 N1 C7 C6 5.4(7)
N2 N1 C7 C2 -0.6(5)
C8 N1 C7 C2 -175.3(4)
C5 C6 C7 N1 179.5(4)
C5 C6 C7 C2 0.3(6)
C3 C2 C7 N1 -179.8(4)
C1 C2 C7 N1 0.4(4)
C3 C2 C7 C6 -0.4(6)
C1 C2 C7 C6 179.8(4)
