#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:11:42 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180292 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/06/7150643.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_7150643
loop_
_publ_author_name
'Shkoor, Mohanad'
'Riahi, Abdolmajid'
'Fatunsin, Olumide'
'Hussain, Ibrar'
'Yawer, Mirza A.'
'Lubbe, Mathias'
'Reim, Stefanie'
'Reinke, Helmut'
'Fischer, Christine'
'Langer, Peter'
_publ_section_title
;
 Diversity-oriented synthesis of 1-hydroxy-2,4-benzodioates by
 regioselective [3+3] cyclocondensations of
 1,3-bis(silyloxy)-1,3-butadienes with 3-alkoxy- and
 3-silyloxy-2-alkoxycarbonyl-2-en-1-ones
;
_journal_issue                   10
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              2182
_journal_page_last               2186
_journal_paper_doi               10.1039/b900542k
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C17 H15 Cl O5'
_chemical_formula_sum            'C17 H15 Cl O5'
_chemical_formula_weight         334.74
_chemical_melting_point          433
_chemical_name_systematic
;
Dimethyl 4'-chloro-2-hydroxy-4-methylbiphenyl-3,5-dicarboxylate
;
_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                 98.435(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.0186(2)
_cell_length_b                   33.9422(15)
_cell_length_c                   11.3074(5)
_cell_measurement_reflns_used    1727
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.76
_cell_measurement_theta_min      3.01
_cell_volume                     1525.65(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0781
_diffrn_reflns_av_sigmaI/netI    0.0799
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8127
_diffrn_reflns_theta_full        24.54
_diffrn_reflns_theta_max         24.54
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_correction_T_min  0.8639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.899
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2550
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.899
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0462P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                1535
_reflns_number_total             2550
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b900542k.txt
_cod_data_source_block           of110(7k)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P2(1)/n '
_cod_database_code               7150643
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.3808(2) 0.26095(2) 1.22315(7) 0.0631(3) Uani 1 1 d . . .
O1 O 0.5887(10) 0.50049(7) 0.8864(2) 0.1499(16) Uani 1 1 d D . .
O2 O 0.7454(6) 0.51329(6) 0.71950(17) 0.0673(6) Uani 1 1 d . . .
O3 O 0.5530(6) 0.43228(7) 0.96884(17) 0.0588(6) Uani 1 1 d . . .
H3O H 0.509(9) 0.4581(11) 0.967(3) 0.100(14) Uiso 1 1 d . . .
O4 O 0.8837(6) 0.38180(6) 0.44957(17) 0.0622(6) Uani 1 1 d . . .
O5 O 1.1145(5) 0.33637(5) 0.57846(15) 0.0470(5) Uani 1 1 d . . .
C1 C 0.7332(6) 0.44583(7) 0.7770(2) 0.0377(7) Uani 1 1 d . . .
C2 C 0.6601(7) 0.41957(8) 0.8679(2) 0.0386(7) Uani 1 1 d . . .
C3 C 0.6910(6) 0.37880(7) 0.8560(2) 0.0324(6) Uani 1 1 d . . .
C4 C 0.7905(6) 0.36520(8) 0.7521(2) 0.0351(7) Uani 1 1 d . . .
H4 H 0.8128 0.3382 0.7427 0.042 Uiso 1 1 calc R . .
C5 C 0.8598(6) 0.38985(8) 0.6601(2) 0.0340(6) Uani 1 1 d . . .
C6 C 0.8377(6) 0.43072(8) 0.6718(2) 0.0360(6) Uani 1 1 d . . .
C7 C 0.6870(8) 0.48822(9) 0.8002(3) 0.0507(8) Uani 1 1 d D . .
C8 C 0.7064(9) 0.55468(8) 0.7440(3) 0.0700(10) Uani 1 1 d . . .
H8A H 0.5743 0.5577 0.8076 0.105 Uiso 0.27(3) 1 calc PR A 1
H8B H 0.5953 0.5675 0.6734 0.105 Uiso 0.27(3) 1 calc PR A 1
H8C H 0.9239 0.5663 0.7671 0.105 Uiso 0.27(3) 1 calc PR A 1
H8D H 0.8135 0.5605 0.8236 0.105 Uiso 0.73(3) 1 calc PR A 2
H8E H 0.4715 0.5610 0.7368 0.105 Uiso 0.73(3) 1 calc PR A 2
H8F H 0.8085 0.5701 0.6877 0.105 Uiso 0.73(3) 1 calc PR A 2
C9 C 0.6139(6) 0.35041(7) 0.9488(2) 0.0331(6) Uani 1 1 d . . .
C10 C 0.7088(7) 0.35689(8) 1.0711(2) 0.0427(7) Uani 1 1 d . . .
H10 H 0.8215 0.3800 1.0965 0.051 Uiso 1 1 calc R . .
C11 C 0.6389(7) 0.32974(9) 1.1549(2) 0.0477(8) Uani 1 1 d . . .
H11 H 0.7042 0.3345 1.2360 0.057 Uiso 1 1 calc R . .
C12 C 0.4716(7) 0.29546(8) 1.1175(2) 0.0404(7) Uani 1 1 d . . .
C13 C 0.3750(6) 0.28814(8) 0.9979(2) 0.0395(7) Uani 1 1 d . . .
H13 H 0.2622 0.2650 0.9731 0.047 Uiso 1 1 calc R . .
C14 C 0.4472(6) 0.31549(7) 0.9150(2) 0.0367(7) Uani 1 1 d . . .
H14 H 0.3822 0.3104 0.8341 0.044 Uiso 1 1 calc R . .
C15 C 0.9507(7) 0.37058(8) 0.5509(2) 0.0396(7) Uani 1 1 d . . .
C16 C 1.2052(8) 0.31409(9) 0.4803(3) 0.0570(9) Uani 1 1 d . . .
H16A H 1.0052 0.3047 0.4316 0.085 Uiso 1 1 calc R . .
H16B H 1.3425 0.2921 0.5104 0.085 Uiso 1 1 calc R . .
H16C H 1.3286 0.3306 0.4331 0.085 Uiso 1 1 calc R . .
C17 C 0.9350(8) 0.45707(8) 0.5747(2) 0.0530(8) Uani 1 1 d . . .
H17A H 0.7356 0.4672 0.5274 0.080 Uiso 1 1 calc R . .
H17B H 1.0620 0.4422 0.5246 0.080 Uiso 1 1 calc R . .
H17C H 1.0693 0.4785 0.6104 0.080 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 C8 117.9(2) . . ?
C2 O3 H3O 112(2) . . ?
C15 O5 C16 116.5(2) . . ?
C6 C1 C2 119.9(2) . . ?
C6 C1 C7 124.2(2) . . ?
C2 C1 C7 115.8(2) . . ?
O3 C2 C3 116.3(2) . . ?
O3 C2 C1 122.4(2) . . ?
C3 C2 C1 121.3(2) . . ?
C4 C3 C2 117.1(2) . . ?
C4 C3 C9 120.1(2) . . ?
C2 C3 C9 122.8(2) . . ?
C3 C4 C5 123.4(2) . . ?
C3 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 C15 117.1(2) . . ?
C6 C5 C15 122.7(2) . . ?
C5 C6 C1 118.0(2) . . ?
C5 C6 C17 119.5(2) . . ?
C1 C6 C17 122.5(2) . . ?
O1 C7 O2 117.9(3) . . ?
O1 C7 C1 123.8(3) . . ?
O2 C7 C1 118.3(2) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
O2 C8 H8D 109.5 . . ?
O2 C8 H8E 109.5 . . ?
H8D C8 H8E 109.5 . . ?
O2 C8 H8F 109.5 . . ?
H8D C8 H8F 109.5 . . ?
H8E C8 H8F 109.5 . . ?
C14 C9 C10 117.3(2) . . ?
C14 C9 C3 120.0(2) . . ?
C10 C9 C3 122.7(2) . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 Cl1 119.6(2) . . ?
C11 C12 Cl1 119.8(2) . . ?
C12 C13 C14 119.3(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C9 121.9(2) . . ?
C13 C14 H14 119.0 . . ?
C9 C14 H14 119.0 . . ?
O4 C15 O5 121.8(2) . . ?
O4 C15 C5 127.2(3) . . ?
O5 C15 C5 110.9(2) . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C17 H17A 109.5 . . ?
C6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C12 1.749(3) . ?
O1 C7 1.180(3) . ?
O2 C7 1.294(3) . ?
O2 C8 1.445(3) . ?
O3 C2 1.348(3) . ?
O3 H3O 0.89(4) . ?
O4 C15 1.200(3) . ?
O5 C15 1.349(3) . ?
O5 C16 1.434(3) . ?
C1 C6 1.414(3) . ?
C1 C2 1.424(3) . ?
C1 C7 1.479(4) . ?
C2 C3 1.398(3) . ?
C3 C4 1.375(3) . ?
C3 C9 1.491(3) . ?
C4 C5 1.394(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(3) . ?
C5 C15 1.490(3) . ?
C6 C17 1.511(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 H8D 0.9600 . ?
C8 H8E 0.9600 . ?
C8 H8F 0.9600 . ?
C9 C14 1.387(3) . ?
C9 C10 1.397(3) . ?
C10 C11 1.380(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(3) . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
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
O3 H3O O1 0.89(4) 1.76(4) 2.508(3) 140(3) .
O3 H3O O1 0.89(4) 2.25(3) 2.913(3) 130(3) 3_667
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O3 -178.6(3) . . . . ?
C7 C1 C2 O3 0.4(4) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
C7 C1 C2 C3 179.4(3) . . . . ?
O3 C2 C3 C4 178.2(2) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
O3 C2 C3 C9 -0.5(4) . . . . ?
C1 C2 C3 C9 -179.5(2) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C9 C3 C4 C5 178.6(2) . . . . ?
C3 C4 C5 C6 1.6(4) . . . . ?
C3 C4 C5 C15 -177.4(2) . . . . ?
C4 C5 C6 C1 -2.0(4) . . . . ?
C15 C5 C6 C1 176.9(2) . . . . ?
C4 C5 C6 C17 176.1(2) . . . . ?
C15 C5 C6 C17 -4.9(4) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
C7 C1 C6 C5 -177.9(3) . . . . ?
C2 C1 C6 C17 -177.0(2) . . . . ?
C7 C1 C6 C17 4.0(4) . . . . ?
C8 O2 C7 O1 3.8(5) . . . . ?
C8 O2 C7 C1 -178.7(3) . . . . ?
C6 C1 C7 O1 177.3(4) . . . . ?
C2 C1 C7 O1 -1.7(5) . . . . ?
C6 C1 C7 O2 0.0(4) . . . . ?
C2 C1 C7 O2 -179.0(3) . . . . ?
C4 C3 C9 C14 -38.9(3) . . . . ?
C2 C3 C9 C14 139.7(3) . . . . ?
C4 C3 C9 C10 139.8(3) . . . . ?
C2 C3 C9 C10 -41.6(4) . . . . ?
C14 C9 C10 C11 -0.2(4) . . . . ?
C3 C9 C10 C11 -178.9(2) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C10 C11 C12 Cl1 -179.8(2) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
Cl1 C12 C13 C14 179.96(19) . . . . ?
C12 C13 C14 C9 -0.3(4) . . . . ?
C10 C9 C14 C13 0.3(4) . . . . ?
C3 C9 C14 C13 179.1(2) . . . . ?
C16 O5 C15 O4 0.1(4) . . . . ?
C16 O5 C15 C5 177.7(2) . . . . ?
C4 C5 C15 O4 145.7(3) . . . . ?
C6 C5 C15 O4 -33.3(4) . . . . ?
C4 C5 C15 O5 -31.7(3) . . . . ?
C6 C5 C15 O5 149.3(2) . . . . ?
