#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/17/7151738.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_7151738
loop_
_publ_author_name
'Malik, Heetika'
'Kohlen, Wouter'
'Jamil, Muhammad'
'Rutjes, Floris P. J. T.'
'Zwanenburg, Binne'
_publ_section_title
;
 Aromatic A-ring analogues of orobanchol, new germination stimulants
 for seeds of parasitic weeds.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2286
_journal_page_last               2293
_journal_paper_doi               10.1039/c0ob00735h
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C17 H14 O6'
_chemical_formula_weight         314.28
_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_date             2006-07-27
_audit_creation_method           'SHELXL, adapted and expanded'
_cell_angle_alpha                90.00
_cell_angle_beta                 94.935(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6845(9)
_cell_length_b                   7.9964(10)
_cell_length_c                   26.937(3)
_cell_measurement_reflns_used    29
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.010
_cell_measurement_theta_min      1.520
_cell_volume                     1434.5(3)
_computing_data_collection
;
Nonius "Collect" program suite (Nonius, 1999)
;
_computing_data_reduction
;
Nonius "EvalCCD" program suite (Duisenberg, 1998)
;
_computing_molecular_graphics
;
PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 18.4
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'area detector φ and ω scan'
_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  0.1277
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            29442
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.52
_diffrn_standards_decay_%        0.000
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS multiscan (Sheldrick, 1996)'
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rather regular thin needle'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.185
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.185
_refine_ls_R_factor_all          0.1350
_refine_ls_R_factor_gt           0.0793
_refine_ls_R_factor_obs          0.0793
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[σ²(Fo²)+(0.0842P)²+0.1052P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1847
_refine_ls_wR_factor_gt          0.1549
_refine_ls_wR_factor_obs         0.1549
_refine_ls_wR_factor_ref         0.1847
_reflns_number_gt                1646
_reflns_number_observed          1646
_reflns_number_total             2536
_reflns_observed_criterion       >2sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00735h.txt
_cod_data_source_block           MALIK4
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (26
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (39 times).

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7151738
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5501(5) 0.3405(4) 0.17543(14) 0.0267(9) Uani 1 d . . .
C2 C 0.6604(5) 0.2613(4) 0.21983(13) 0.0250(9) Uani 1 d . . .
H2 H 0.7012 0.1475 0.2117 0.030 Uiso 1 calc R . .
C3 C 0.8446(5) 0.3607(4) 0.24486(13) 0.0247(9) Uani 1 d . . .
H3 H 0.9645 0.2897 0.2471 0.030 Uiso 1 calc R . .
C4 C 0.7845(5) 0.3980(5) 0.29620(13) 0.0264(9) Uani 1 d . . .
C5 C 0.8954(6) 0.4801(5) 0.33454(15) 0.0405(11) Uani 1 d . . .
H5 H 1.0220 0.5222 0.3297 0.049 Uiso 1 calc R . .
C6 C 0.8174(7) 0.4990(6) 0.37954(16) 0.0495(12) Uani 1 d . . .
H6 H 0.8925 0.5523 0.4056 0.059 Uiso 1 calc R . .
C7 C 0.6281(7) 0.4395(6) 0.38657(16) 0.0509(12) Uani 1 d . . .
H7 H 0.5765 0.4545 0.4172 0.061 Uiso 1 calc R . .
C8 C 0.5150(6) 0.3587(5) 0.34902(15) 0.0398(11) Uani 1 d . . .
H8 H 0.3879 0.3179 0.3540 0.048 Uiso 1 calc R . .
C9 C 0.5947(5) 0.3392(4) 0.30356(14) 0.0268(9) Uani 1 d . . .
C10 C 0.5003(5) 0.2559(5) 0.25775(13) 0.0273(9) Uani 1 d . . .
H10 H 0.4614 0.1406 0.2647 0.033 Uiso 1 calc R . .
O11 O 0.3285(3) 0.3529(3) 0.23579(9) 0.0297(7) Uani 1 d . . .
C12 C 0.3526(5) 0.3935(5) 0.18802(14) 0.0290(9) Uani 1 d . . .
O13 O 0.8845(3) 0.5133(3) 0.22046(9) 0.0282(7) Uani 1 d . . .
H13 H 0.9807 0.5007 0.2039 0.042 Uiso 1 calc R . .
O14 O 0.2188(4) 0.4645(3) 0.16300(10) 0.0357(7) Uani 1 d . . .
C15 C 0.6162(5) 0.3730(5) 0.13155(14) 0.0311(10) Uani 1 d . . .
H15 H 0.5354 0.4300 0.1073 0.037 Uiso 1 calc R . .
O16 O 0.8029(3) 0.3224(3) 0.12223(9) 0.0360(7) Uani 1 d . . .
C17 C 0.8934(6) 0.4008(6) 0.08317(14) 0.0393(11) Uani 1 d . . .
H17 H 1.0351 0.3680 0.0850 0.047 Uiso 1 calc R . .
O18 O 0.7972(4) 0.3469(4) 0.03603(10) 0.0493(9) Uani 1 d . . .
C19 C 0.7464(6) 0.4867(8) 0.00855(17) 0.0563(14) Uani 1 d . . .
C20 C 0.7962(6) 0.6353(7) 0.03816(18) 0.0524(14) Uani 1 d . . .
C21 C 0.8810(6) 0.5858(6) 0.08176(16) 0.0412(11) Uani 1 d . . .
H21 H 0.9262 0.6566 0.1077 0.049 Uiso 1 calc R . .
O22 O 0.6750(5) 0.4747(6) -0.03397(11) 0.0831(14) Uani 1 d . . .
C23 C 0.7543(9) 0.8071(8) 0.0184(2) 0.091(2) Uani 1 d . . .
H23A H 0.7809 0.8871 0.0448 0.136 Uiso 1 calc R . .
H23B H 0.6161 0.8149 0.0056 0.136 Uiso 1 calc R . .
H23C H 0.8390 0.8300 -0.0078 0.136 Uiso 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'
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
C15 C1 C12 122.1(3) . . y
C15 C1 C2 128.3(3) . . y
C12 C1 C2 109.5(3) . . y
C1 C2 C10 102.7(3) . . y
C1 C2 C3 116.4(3) . . y
C10 C2 C3 107.1(3) . . y
O13 C3 C4 109.3(3) . . y
O13 C3 C2 114.1(3) . . y
C4 C3 C2 103.5(3) . . y
C9 C4 C5 119.6(3) . . y
C9 C4 C3 112.7(3) . . y
C5 C4 C3 127.8(3) . . y
C6 C5 C4 119.5(4) . . y
C5 C6 C7 120.5(4) . . y
C8 C7 C6 121.0(4) . . y
C7 C8 C9 118.4(4) . . y
C4 C9 C8 121.1(4) . . y
C4 C9 C10 111.1(3) . . y
C8 C9 C10 127.8(3) . . y
O11 C10 C9 110.9(3) . . y
O11 C10 C2 106.4(3) . . y
C9 C10 C2 105.5(3) . . y
C12 O11 C10 111.0(3) . . y
O14 C12 O11 120.0(3) . . y
O14 C12 C1 130.3(4) . . y
O11 C12 C1 109.7(3) . . y
C1 C15 O16 119.4(3) . . y
C15 O16 C17 117.9(3) . . y
O16 C17 O18 109.8(3) . . y
O16 C17 C21 115.9(3) . . y
O18 C17 C21 104.9(3) . . y
C19 O18 C17 107.7(4) . . y
O22 C19 O18 120.6(5) . . y
O22 C19 C20 129.7(5) . . y
O18 C19 C20 109.7(4) . . y
C21 C20 C19 107.7(4) . . y
C21 C20 C23 130.3(6) . . y
C19 C20 C23 122.1(5) . . y
C20 C21 C17 109.9(4) . . y
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
C1 C15 1.323(5) . y
C1 C12 1.454(5) . y
C1 C2 1.491(5) . y
C2 C10 1.542(5) . y
C2 C3 1.568(5) . y
C3 O13 1.422(4) . y
C3 C4 1.503(5) . y
C4 C9 1.383(5) . y
C4 C5 1.384(5) . y
C5 C6 1.369(6) . y
C6 C7 1.380(6) . y
C7 C8 1.372(6) . y
C8 C9 1.385(5) . y
C9 C10 1.494(5) . y
C10 O11 1.467(4) . y
O11 C12 1.350(4) . y
C12 O14 1.213(4) . y
C15 O16 1.356(4) . y
O16 C17 1.406(5) . y
C17 O18 1.439(4) . y
C17 C21 1.482(6) . y
O18 C19 1.367(6) . y
C19 O22 1.206(5) . y
C19 C20 1.454(7) . y
C20 C21 1.320(6) . y
C20 C23 1.490(7) . y
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
O13 H13 O14 0.82 2.03 2.853(3) 178.9 1_655
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26994270
