#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:55:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180323 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/37/7153703.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_7153703
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            'C8 H9 Cl O3'
_chemical_formula_weight         188.60
_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                 95.8337(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.214(3)
_cell_length_b                   10.0193(13)
_cell_length_c                   8.1960(11)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.87
_cell_volume                     1651.3(4)
_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 1.000
_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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0143
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            24945
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.423
_exptl_absorpt_correction_T_max  0.9669
_exptl_absorpt_correction_T_min  0.8357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4092
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0259
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0256P)²+0.9189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0643
_refine_ls_wR_factor_ref         0.0662
_reflns_number_gt                3775
_reflns_number_total             4092
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00391h2.cif
_cod_data_source_block           13spz12h2
_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_sg_symbol_H-M      'P 21/c'
_cod_database_code               7153703
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 0.650566(13) 0.75728(3) 0.54493(3) 0.01970(7) Uani 1 1 d .
O1 O 0.67152(4) 0.97987(8) 0.33080(10) 0.01491(16) Uani 1 1 d D
H1O H 0.6771(7) 1.0515(11) 0.2814(17) 0.022 Uiso 1 1 d D
O2 O 0.40829(4) 0.83787(8) 0.36423(10) 0.01554(16) Uani 1 1 d .
O3 O 0.28886(4) 0.69419(8) 0.31976(11) 0.01913(18) Uani 1 1 d D
H3O H 0.2514(5) 0.6700(16) 0.3407(19) 0.029 Uiso 1 1 d D
C1 C 0.60560(5) 0.94917(11) 0.33058(13) 0.0120(2) Uani 1 1 d .
C2 C 0.58791(5) 0.84532(11) 0.43068(13) 0.0124(2) Uani 1 1 d .
C3 C 0.52218(5) 0.80962(11) 0.43938(13) 0.0129(2) Uani 1 1 d .
H3 H 0.5113 0.7397 0.5103 0.016 Uiso 1 1 calc R
C4 C 0.47213(5) 0.87719(11) 0.34308(13) 0.0126(2) Uani 1 1 d .
C5 C 0.48874(5) 0.97882(11) 0.23867(13) 0.0143(2) Uani 1 1 d .
H5 H 0.4549 1.0237 0.1709 0.017 Uiso 1 1 calc R
C6 C 0.55528(5) 1.01461(11) 0.23389(13) 0.0140(2) Uani 1 1 d .
H6 H 0.5663 1.0847 0.1635 0.017 Uiso 1 1 calc R
C7 C 0.35691(5) 0.87498(12) 0.23992(15) 0.0186(2) Uani 1 1 d .
H7A H 0.3632 0.8286 0.1359 0.022 Uiso 1 1 calc R
H7B H 0.3581 0.9724 0.2204 0.022 Uiso 1 1 calc R
C8 C 0.29137(5) 0.83576(12) 0.29838(16) 0.0191(2) Uani 1 1 d .
H8A H 0.2860 0.8808 0.4037 0.023 Uiso 1 1 calc R
H8B H 0.2545 0.8645 0.2172 0.023 Uiso 1 1 calc R
Cl2 Cl 1.153405(13) 0.79662(3) 0.51434(3) 0.01903(7) Uani 1 1 d .
O4 O 1.17121(4) 0.54214(8) 0.35464(10) 0.01407(16) Uani 1 1 d D
H4O H 1.1763(7) 0.4707(11) 0.3039(16) 0.021 Uiso 1 1 d D
O5 O 0.90962(4) 0.69697(8) 0.38669(10) 0.01502(16) Uani 1 1 d .
O6 O 0.78644(4) 0.82846(8) 0.29972(11) 0.02051(18) Uani 1 1 d D
H6O H 0.7509(6) 0.8590(16) 0.3239(19) 0.031 Uiso 1 1 d D
C9 C 1.10548(5) 0.57581(11) 0.35360(13) 0.0122(2) Uani 1 1 d .
C10 C 1.08946(5) 0.69358(11) 0.43098(13) 0.0125(2) Uani 1 1 d .
C11 C 1.02404(5) 0.73168(11) 0.44106(13) 0.0129(2) Uani 1 1 d .
H11 H 1.0143 0.8109 0.4976 0.015 Uiso 1 1 calc R
C12 C 0.97280(5) 0.65245(11) 0.36739(13) 0.0125(2) Uani 1 1 d .
C13 C 0.98763(5) 0.53675(11) 0.28422(13) 0.0140(2) Uani 1 1 d .
H13 H 0.9528 0.4838 0.2312 0.017 Uiso 1 1 calc R
C14 C 1.05384(5) 0.49901(11) 0.27920(13) 0.0139(2) Uani 1 1 d .
H14 H 1.0637 0.4193 0.2238 0.017 Uiso 1 1 calc R
C15 C 0.85562(5) 0.63384(11) 0.28992(14) 0.0153(2) Uani 1 1 d .
H15A H 0.8571 0.5361 0.3080 0.018 Uiso 1 1 calc R
H15B H 0.8586 0.6513 0.1720 0.018 Uiso 1 1 calc R
C16 C 0.79188(5) 0.69036(11) 0.34100(14) 0.0157(2) Uani 1 1 d .
H16A H 0.7536 0.6412 0.2851 0.019 Uiso 1 1 calc R
H16B H 0.7910 0.6793 0.4608 0.019 Uiso 1 1 calc R
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 H1O 111.8(10)
C4 O2 C7 117.30(9)
C8 O3 H3O 111.1(11)
O1 C1 C6 123.48(10)
O1 C1 C2 118.38(9)
C6 C1 C2 118.13(10)
C3 C2 C1 121.86(10)
C3 C2 Cl1 119.46(8)
C1 C2 Cl1 118.67(8)
C2 C3 C4 119.37(10)
C2 C3 H3 120.3
C4 C3 H3 120.3
O2 C4 C5 125.03(10)
O2 C4 C3 115.17(9)
C5 C4 C3 119.78(10)
C4 C5 C6 119.87(10)
C4 C5 H5 120.1
C6 C5 H5 120.1
C1 C6 C5 120.96(10)
C1 C6 H6 119.5
C5 C6 H6 119.5
O2 C7 C8 107.73(10)
O2 C7 H7A 110.2
C8 C7 H7A 110.2
O2 C7 H7B 110.2
C8 C7 H7B 110.2
H7A C7 H7B 108.5
O3 C8 C7 109.93(9)
O3 C8 H8A 109.7
C7 C8 H8A 109.7
O3 C8 H8B 109.7
C7 C8 H8B 109.7
H8A C8 H8B 108.2
C9 O4 H4O 112.1(10)
C12 O5 C15 117.23(8)
C16 O6 H6O 110.6(12)
O4 C9 C14 123.52(10)
O4 C9 C10 118.41(9)
C14 C9 C10 118.07(10)
C11 C10 C9 121.83(10)
C11 C10 Cl2 119.23(8)
C9 C10 Cl2 118.93(8)
C10 C11 C12 119.26(10)
C10 C11 H11 120.4
C12 C11 H11 120.4
O5 C12 C13 125.03(10)
O5 C12 C11 115.03(9)
C13 C12 C11 119.93(10)
C12 C13 C14 119.65(10)
C12 C13 H13 120.2
C14 C13 H13 120.2
C9 C14 C13 121.19(10)
C9 C14 H14 119.4
C13 C14 H14 119.4
O5 C15 C16 107.82(9)
O5 C15 H15A 110.1
C16 C15 H15A 110.1
O5 C15 H15B 110.1
C16 C15 H15B 110.1
H15A C15 H15B 108.5
O6 C16 C15 110.28(9)
O6 C16 H16A 109.6
C15 C16 H16A 109.6
O6 C16 H16B 109.6
C15 C16 H16B 109.6
H16A C16 H16B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.7372(11)
O1 C1 1.3674(12)
O1 H1O 0.838(9)
O2 C4 1.3769(13)
O2 C7 1.4282(13)
O3 C8 1.4307(14)
O3 H3O 0.829(9)
C1 C6 1.3887(15)
C1 C2 1.3940(15)
C2 C3 1.3848(14)
C3 C4 1.3936(15)
C3 H3 0.9500
C4 C5 1.3930(15)
C5 C6 1.3963(15)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.5061(16)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9900
C8 H8B 0.9900
Cl2 C10 1.7389(11)
O4 C9 1.3699(12)
O4 H4O 0.840(9)
O5 C12 1.3770(12)
O5 C15 1.4298(13)
O6 C16 1.4260(13)
O6 H6O 0.823(9)
C9 C14 1.3871(15)
C9 C10 1.3933(15)
C10 C11 1.3869(14)
C11 C12 1.3929(15)
C11 H11 0.9500
C12 C13 1.3928(15)
C13 C14 1.3954(15)
C13 H13 0.9500
C14 H14 0.9500
C15 C16 1.5053(15)
C15 H15A 0.9900
C15 H15B 0.9900
C16 H16A 0.9900
C16 H16B 0.9900
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
O1 H1O O3 0.838(9) 1.822(9) 2.6413(12) 165.5(14) 2_655
O6 H6O O1 0.823(9) 2.016(10) 2.8076(11) 161.2(16) .
O4 H4O O6 0.840(9) 1.857(9) 2.6716(12) 163.2(14) 2_745
O3 H3O O4 0.829(9) 2.079(10) 2.8630(11) 157.7(16) 1_455
