#------------------------------------------------------------------------------
#$Date: 2016-03-22 20:26:17 +0100 (mar 22 de mar de 2016) $
#$Revision: 179019 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/17/4121745.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_4121745
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 H10 Cl2 O2'
_chemical_formula_sum            'C8 H10 Cl2 O2'
_chemical_formula_weight         209.06
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 102.969(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4893(7)
_cell_length_b                   11.3222(11)
_cell_length_c                   11.1631(10)
_cell_measurement_reflns_used    5531
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.60
_cell_volume                     922.43(15)
_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 0.992
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       'φ and 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  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14108
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  0.9492
_exptl_absorpt_correction_T_min  0.8579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLADE
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0320
_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)+(0.0297P)²+0.5610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0702
_reflns_number_gt                1559
_reflns_number_total             1883
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5031744_si_012.cif
_cod_data_source_block           baran380
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      P2(1)/c
_cod_database_code               4121745
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_refinement_flags
Cl1 Cl 0.22809(6) 0.47998(4) 0.61831(4) 0.01532(13) Uani 1 1 d .
Cl2 Cl 0.64932(7) 0.13644(5) 0.62008(5) 0.02381(14) Uani 1 1 d .
O1 O 0.03922(18) 0.29268(13) 0.45514(13) 0.0250(3) Uani 1 1 d .
O2 O 0.60964(16) 0.42885(12) 0.66588(12) 0.0158(3) Uani 1 1 d .
C1 C 0.3295(2) 0.36830(16) 0.55081(16) 0.0124(4) Uani 1 1 d .
C2 C 0.2055(3) 0.28806(17) 0.46794(18) 0.0164(4) Uani 1 1 d .
C3 C 0.2951(3) 0.19671(18) 0.40283(18) 0.0199(4) Uani 1 1 d .
H3A H 0.2196 0.1856 0.3186 0.024 Uiso 1 1 calc R
H3B H 0.2984 0.1205 0.4467 0.024 Uiso 1 1 calc R
C4 C 0.4893(3) 0.22956(18) 0.39474(18) 0.0203(4) Uani 1 1 d .
H4A H 0.5466 0.1614 0.3623 0.024 Uiso 1 1 calc R
H4B H 0.4844 0.2960 0.3365 0.024 Uiso 1 1 calc R
C5 C 0.6063(3) 0.26457(17) 0.51844(17) 0.0170(4) Uani 1 1 d .
H5A H 0.7259 0.2962 0.5068 0.020 Uiso 1 1 calc R
C6 C 0.5142(2) 0.35692(17) 0.58007(16) 0.0132(4) Uani 1 1 d .
C7 C 0.8081(2) 0.4181(2) 0.70769(18) 0.0220(5) Uani 1 1 d .
H7A H 0.8692 0.4354 0.6397 0.026 Uiso 1 1 calc R
H7B H 0.8419 0.3372 0.7382 0.026 Uiso 1 1 calc R
C8 C 0.8633(3) 0.5066(2) 0.8094(2) 0.0265(5) Uani 1 1 d .
H8A H 0.9962 0.5033 0.8413 0.040 Uiso 1 1 calc R
H8B H 0.8012 0.4884 0.8757 0.040 Uiso 1 1 calc R
H8C H 0.8284 0.5860 0.7777 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 0.0123(2) 0.0155(2) 0.0190(2) -0.00245(19) 0.00521(17) 0.00229(17)
Cl2 0.0282(3) 0.0199(3) 0.0243(3) 0.0060(2) 0.0080(2) 0.0110(2)
O1 0.0126(7) 0.0265(9) 0.0340(9) -0.0067(7) 0.0009(6) -0.0001(6)
O2 0.0084(6) 0.0202(8) 0.0179(7) -0.0012(6) 0.0012(5) -0.0008(5)
C1 0.0135(9) 0.0123(9) 0.0126(9) 0.0013(7) 0.0053(7) 0.0036(7)
C2 0.0178(10) 0.0138(10) 0.0168(10) 0.0020(8) 0.0024(8) 0.0010(8)
C3 0.0212(10) 0.0198(11) 0.0182(10) -0.0052(8) 0.0032(8) 0.0001(8)
C4 0.0241(11) 0.0223(12) 0.0170(11) -0.0009(8) 0.0101(8) 0.0062(8)
C5 0.0173(9) 0.0178(11) 0.0180(10) 0.0043(8) 0.0083(8) 0.0055(8)
C6 0.0157(9) 0.0153(10) 0.0098(9) 0.0045(8) 0.0055(7) 0.0008(7)
C7 0.0091(9) 0.0354(13) 0.0208(11) 0.0021(9) 0.0019(8) -0.0003(8)
C8 0.0160(10) 0.0319(13) 0.0290(12) 0.0005(10) -0.0005(9) -0.0044(9)
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'
O O 0.0106 0.0060 '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
C6 O2 C7 121.41(15)
C6 C1 C2 124.07(17)
C6 C1 Cl1 119.23(15)
C2 C1 Cl1 116.65(13)
O1 C2 C1 122.05(17)
O1 C2 C3 121.71(17)
C1 C2 C3 116.20(16)
C2 C3 C4 113.31(16)
C2 C3 H3A 108.9
C4 C3 H3A 108.9
C2 C3 H3B 108.9
C4 C3 H3B 108.9
H3A C3 H3B 107.7
C5 C4 C3 112.01(16)
C5 C4 H4A 109.2
C3 C4 H4A 109.2
C5 C4 H4B 109.2
C3 C4 H4B 109.2
H4A C4 H4B 107.9
C6 C5 C4 111.68(15)
C6 C5 Cl2 107.68(12)
C4 C5 Cl2 110.15(14)
C6 C5 H5A 109.1
C4 C5 H5A 109.1
Cl2 C5 H5A 109.1
O2 C6 C1 117.93(16)
O2 C6 C5 121.74(16)
C1 C6 C5 120.33(17)
O2 C7 C8 105.90(16)
O2 C7 H7A 110.6
C8 C7 H7A 110.6
O2 C7 H7B 110.6
C8 C7 H7B 110.6
H7A C7 H7B 108.7
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 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 1.7322(18)
Cl2 C5 1.8253(19)
O1 C2 1.222(2)
O2 C6 1.336(2)
O2 C7 1.459(2)
C1 C6 1.354(2)
C1 C2 1.469(3)
C2 C3 1.506(3)
C3 C4 1.524(3)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.513(3)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.502(3)
C5 H5A 1.0000
C7 C8 1.502(3)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4A O2 0.99 2.56 3.404(2) 143.5 4_565
C5 H5A O1 1.00 2.54 3.485(2) 157.6 1_655
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 C1 C2 O1 171.12(18)
Cl1 C1 C2 O1 -6.3(3)
C6 C1 C2 C3 -6.8(3)
Cl1 C1 C2 C3 175.81(13)
O1 C2 C3 C4 160.36(18)
C1 C2 C3 C4 -21.7(2)
C2 C3 C4 C5 50.7(2)
C3 C4 C5 C6 -51.3(2)
C3 C4 C5 Cl2 68.28(18)
C7 O2 C6 C1 176.55(17)
C7 O2 C6 C5 -2.5(3)
C2 C1 C6 O2 -173.50(16)
Cl1 C1 C6 O2 3.8(2)
C2 C1 C6 C5 5.6(3)
Cl1 C1 C6 C5 -177.08(13)
C4 C5 C6 O2 -156.92(17)
Cl2 C5 C6 O2 82.02(18)
C4 C5 C6 C1 24.0(2)
Cl2 C5 C6 C1 -97.03(18)
C6 O2 C7 C8 -175.91(16)
