#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:55:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180323 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/37/7153702.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_7153702
loop_
_publ_author_name
'Yin, Zhiwei'
'Zhang, Jinzhu'
'Wu, Jing'
'Green, Riana'
'Li, Sihan'
'Zheng, Shengping'
_publ_section_title
;
 Synthesis of o-chlorophenols via an unexpected nucleophilic chlorination
 of quinone monoketals mediated by N,N'-dimethylhydrazine dihydrochloride.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2854
_journal_page_last               2858
_journal_paper_doi               10.1039/c4ob00391h
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C9 H11 Cl O3'
_chemical_formula_weight         202.63
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.227(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.2268(5)
_cell_length_b                   8.9268(9)
_cell_length_c                   19.809(2)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.49
_cell_measurement_theta_min      2.50
_cell_volume                     923.56(16)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II 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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0104
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19279
_diffrn_reflns_theta_full        28.49
_diffrn_reflns_theta_max         28.49
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  0.9238
_exptl_absorpt_correction_T_min  0.8196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2312
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0260
_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)+(0.0342P)²+0.4173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0699
_reflns_number_gt                2246
_reflns_number_total             2312
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00391h2.cif
_cod_data_source_block           13spz2h
_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/RSC/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 
;
_cod_original_cell_volume        923.59(16)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7153702
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_refinement_flags
Cl1 Cl 0.72171(5) 0.30994(3) 0.089241(12) 0.01932(8) Uani 1 1 d .
O1 O 0.59696(14) 0.45612(9) 0.33668(3) 0.01759(16) Uani 1 1 d .
O2 O 0.63349(14) 0.16443(8) 0.45716(4) 0.01781(16) Uani 1 1 d D
H2O H 0.731(3) 0.1175(17) 0.4833(7) 0.036(4) Uiso 1 1 d D
O3 O 0.30364(14) 0.52223(9) 0.06639(3) 0.01717(16) Uani 1 1 d D
H3O H 0.165(2) 0.5693(17) 0.0632(8) 0.036(4) Uiso 1 1 d D
C1 C 0.53203(18) 0.46773(11) 0.26913(5) 0.01359(18) Uani 1 1 d .
C2 C 0.33313(18) 0.56652(11) 0.25169(5) 0.01438(18) Uani 1 1 d .
H2 H 0.2527 0.6219 0.2859 0.017 Uiso 1 1 calc R
C3 C 0.25256(18) 0.58402(11) 0.18452(5) 0.01462(19) Uani 1 1 d .
H3 H 0.1159 0.6508 0.1733 0.018 Uiso 1 1 calc R
C4 C 0.36965(18) 0.50479(11) 0.13322(5) 0.01317(18) Uani 1 1 d .
C5 C 0.56812(18) 0.40777(11) 0.15171(5) 0.01325(18) Uani 1 1 d .
C6 C 0.65121(18) 0.38763(11) 0.21885(5) 0.01407(18) Uani 1 1 d .
H6 H 0.7870 0.3203 0.2301 0.017 Uiso 1 1 calc R
C7 C 0.82364(18) 0.37157(12) 0.35434(5) 0.01603(19) Uani 1 1 d .
H7A H 0.9710 0.4104 0.3297 0.019 Uiso 1 1 calc R
H7B H 0.7984 0.2648 0.3423 0.019 Uiso 1 1 calc R
C8 C 0.87306(19) 0.38801(12) 0.42990(5) 0.0167(2) Uani 1 1 d .
H8A H 0.8905 0.4957 0.4411 0.020 Uiso 1 1 calc R
H8B H 1.0371 0.3384 0.4429 0.020 Uiso 1 1 calc R
C9 C 0.66197(19) 0.32107(11) 0.47090(5) 0.0160(2) Uani 1 1 d .
H9A H 0.7033 0.3359 0.5196 0.019 Uiso 1 1 calc R
H9B H 0.4986 0.3731 0.4597 0.019 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 0.02488(14) 0.01820(13) 0.01499(13) -0.00193(8) 0.00238(9) 0.00626(9)
O1 0.0200(4) 0.0214(4) 0.0111(3) 0.0013(3) -0.0031(3) 0.0058(3)
O2 0.0196(4) 0.0160(3) 0.0174(3) 0.0040(3) -0.0054(3) -0.0040(3)
O3 0.0192(4) 0.0209(4) 0.0110(3) -0.0001(3) -0.0033(3) 0.0046(3)
C1 0.0151(4) 0.0144(4) 0.0112(4) 0.0022(3) -0.0014(3) -0.0014(3)
C2 0.0143(4) 0.0157(4) 0.0132(4) 0.0001(3) 0.0008(3) 0.0009(3)
C3 0.0130(4) 0.0164(4) 0.0143(4) 0.0011(3) -0.0012(3) 0.0021(3)
C4 0.0139(4) 0.0137(4) 0.0117(4) 0.0011(3) -0.0015(3) -0.0018(3)
C5 0.0152(4) 0.0121(4) 0.0126(4) -0.0004(3) 0.0015(3) -0.0003(3)
C6 0.0144(4) 0.0135(4) 0.0142(4) 0.0023(3) -0.0009(3) 0.0015(3)
C7 0.0133(4) 0.0201(5) 0.0145(4) 0.0045(4) -0.0017(3) 0.0006(4)
C8 0.0168(4) 0.0174(5) 0.0155(4) 0.0033(4) -0.0052(3) -0.0041(4)
C9 0.0177(5) 0.0172(5) 0.0129(4) 0.0001(3) -0.0019(3) -0.0001(3)
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
C1 O1 C7 116.60(8)
C9 O2 H2O 108.6(12)
C4 O3 H3O 108.4(11)
O1 C1 C6 123.95(9)
O1 C1 C2 116.28(8)
C6 C1 C2 119.78(9)
C3 C2 C1 120.21(9)
C3 C2 H2 119.9
C1 C2 H2 119.9
C2 C3 C4 120.96(9)
C2 C3 H3 119.5
C4 C3 H3 119.5
O3 C4 C5 119.02(9)
O3 C4 C3 123.11(9)
C5 C4 C3 117.83(8)
C4 C5 C6 122.24(9)
C4 C5 Cl1 119.11(7)
C6 C5 Cl1 118.64(7)
C1 C6 C5 118.98(9)
C1 C6 H6 120.5
C5 C6 H6 120.5
O1 C7 C8 107.26(8)
O1 C7 H7A 110.3
C8 C7 H7A 110.3
O1 C7 H7B 110.3
C8 C7 H7B 110.3
H7A C7 H7B 108.5
C7 C8 C9 113.00(8)
C7 C8 H8A 109.0
C9 C8 H8A 109.0
C7 C8 H8B 109.0
C9 C8 H8B 109.0
H8A C8 H8B 107.8
O2 C9 C8 110.81(8)
O2 C9 H9A 109.5
C8 C9 H9A 109.5
O2 C9 H9B 109.5
C8 C9 H9B 109.5
H9A C9 H9B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C5 1.7366(10)
O1 C1 1.3716(11)
O1 C7 1.4365(12)
O2 C9 1.4312(12)
O2 H2O 0.826(9)
O3 C4 1.3639(11)
O3 H3O 0.836(9)
C1 C6 1.3928(13)
C1 C2 1.3964(13)
C2 C3 1.3888(13)
C2 H2 0.9500
C3 C4 1.3985(13)
C3 H3 0.9500
C4 C5 1.3896(13)
C5 C6 1.3945(13)
C6 H6 0.9500
C7 C8 1.5161(13)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.5179(14)
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9900
C9 H9B 0.9900
