#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/17/7151736.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_7151736
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
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                91.219(4)
_cell_angle_beta                 96.917(6)
_cell_angle_gamma                94.850(4)
_cell_formula_units_Z            2
_cell_length_a                   6.8264(3)
_cell_length_b                   8.0831(3)
_cell_length_c                   12.8838(11)
_cell_measurement_reflns_used    112
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.520
_cell_measurement_theta_min      1.590
_cell_volume                     702.85(7)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17511
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         1.59
_diffrn_standards_decay_%        0.000
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS multiscan (Sheldrick, 1996)'
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rather regular rod'
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.076
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1218
_refine_ls_R_factor_gt           0.1001
_refine_ls_R_factor_obs          0.1001
_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)+(0.1523P)²+2.8792P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.3089
_refine_ls_wR_factor_gt          0.2932
_refine_ls_wR_factor_obs         0.2932
_refine_ls_wR_factor_ref         0.3089
_reflns_number_gt                2491
_reflns_number_observed          2491
_reflns_number_total             3233
_reflns_observed_criterion       >2sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00735h.txt
_cod_data_source_block           MALIK2
_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_database_code               7151736
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.1391(6) 0.1905(5) 0.7541(3) 0.0214(8) Uani 1 d . . .
C2 C 0.0832(6) 0.3573(5) 0.7201(3) 0.0205(8) Uani 1 d . . .
H2 H 0.0740 0.3640 0.6438 0.025 Uiso 1 calc R . .
C3 C -0.1072(6) 0.4144(5) 0.7608(3) 0.0231(9) Uani 1 d . . .
H3 H -0.1797 0.3220 0.7918 0.028 Uiso 1 calc R . .
C4 C -0.0299(6) 0.5480(5) 0.8423(3) 0.0206(8) Uani 1 d . . .
C5 C -0.1388(7) 0.6348(6) 0.9042(3) 0.0266(9) Uani 1 d . . .
H5 H -0.2749 0.6097 0.9011 0.032 Uiso 1 calc R . .
C6 C -0.0423(8) 0.7603(6) 0.9712(3) 0.0303(10) Uani 1 d . . .
H6 H -0.1145 0.8225 1.0120 0.036 Uiso 1 calc R . .
C7 C 0.1607(8) 0.7933(5) 0.9775(4) 0.0301(10) Uani 1 d . . .
H7 H 0.2238 0.8763 1.0240 0.036 Uiso 1 calc R . .
C8 C 0.2714(7) 0.7062(5) 0.9167(4) 0.0273(9) Uani 1 d . . .
H8 H 0.4080 0.7297 0.9212 0.033 Uiso 1 calc R . .
C9 C 0.1739(6) 0.5817(5) 0.8479(3) 0.0208(8) Uani 1 d . . .
C10 C 0.2608(6) 0.4726(5) 0.7736(3) 0.0225(9) Uani 1 d . . .
H10 H 0.3246 0.5386 0.7220 0.027 Uiso 1 calc R . .
O11 O 0.3991(4) 0.3680(4) 0.8294(3) 0.0281(7) Uani 1 d . . .
C12 C 0.3339(6) 0.2061(5) 0.8170(3) 0.0233(9) Uani 1 d . . .
O13 O -0.2319(5) 0.4860(4) 0.6809(3) 0.0311(8) Uani 1 d . . .
H13 H -0.3262 0.4191 0.6600 0.047 Uiso 1 calc R . .
O14 O 0.4299(5) 0.0989(4) 0.8541(3) 0.0346(8) Uani 1 d . . .
C15 C 0.0366(6) 0.0443(5) 0.7369(3) 0.0232(9) Uani 1 d . . .
H15 H 0.0912 -0.0504 0.7627 0.028 Uiso 1 calc R . .
O16 O -0.1471(5) 0.0302(3) 0.6821(3) 0.0274(7) Uani 1 d . . .
C17 C -0.2382(6) -0.1329(5) 0.6624(3) 0.0225(9) Uani 1 d . . .
H17 H -0.1740 -0.2102 0.7104 0.027 Uiso 1 calc R . .
O18 O -0.2228(4) -0.1806(4) 0.5555(2) 0.0276(7) Uani 1 d . . .
C19 C -0.4073(6) -0.2333(5) 0.5096(3) 0.0250(9) Uani 1 d . . .
C20 C -0.5540(6) -0.2066(5) 0.5811(3) 0.0222(8) Uani 1 d . . .
C21 C -0.4533(6) -0.1419(5) 0.6700(3) 0.0233(9) Uani 1 d . . .
H21 H -0.5100 -0.1075 0.7280 0.028 Uiso 1 calc R . .
O22 O -0.4329(5) -0.2919(5) 0.4218(3) 0.0418(10) Uani 1 d . . .
C23 C -0.7687(7) -0.2500(7) 0.5521(4) 0.0331(11) Uani 1 d . . .
H23A H -0.8361 -0.2392 0.6128 0.050 Uiso 1 calc R . .
H23B H -0.7907 -0.3624 0.5250 0.050 Uiso 1 calc R . .
H23C H -0.8188 -0.1765 0.4997 0.050 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 120.8(4) . . y
C15 C1 C2 128.9(4) . . y
C12 C1 C2 110.2(3) . . y
C1 C2 C10 101.7(3) . . y
C1 C2 C3 115.4(3) . . y
C10 C2 C3 107.2(3) . . y
O13 C3 C4 108.2(3) . . y
O13 C3 C2 111.9(4) . . y
C4 C3 C2 104.0(3) . . y
C5 C4 C9 121.1(4) . . y
C5 C4 C3 127.1(4) . . y
C9 C4 C3 111.8(4) . . y
C4 C5 C6 118.8(4) . . y
C7 C6 C5 120.2(4) . . y
C8 C7 C6 121.4(4) . . y
C7 C8 C9 118.4(4) . . y
C4 C9 C8 120.0(4) . . y
C4 C9 C10 111.7(4) . . y
C8 C9 C10 128.2(4) . . y
O11 C10 C9 111.1(3) . . y
O11 C10 C2 107.5(3) . . y
C9 C10 C2 104.9(3) . . y
C12 O11 C10 111.5(3) . . y
O14 C12 O11 121.9(4) . . y
O14 C12 C1 129.1(4) . . y
O11 C12 C1 109.0(3) . . y
C1 C15 O16 121.0(4) . . y
C15 O16 C17 116.3(3) . . y
O16 C17 O18 108.4(3) . . y
O16 C17 C21 111.9(3) . . y
O18 C17 C21 105.0(3) . . y
C19 O18 C17 107.6(3) . . y
O22 C19 O18 120.8(4) . . y
O22 C19 C20 128.9(4) . . y
O18 C19 C20 110.3(4) . . y
C21 C20 C19 106.6(4) . . y
C21 C20 C23 130.7(4) . . y
C19 C20 C23 122.7(4) . . 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 1.322(6) . y
C1 C12 1.466(6) . y
C1 C2 1.492(6) . y
C2 C10 1.547(6) . y
C2 C3 1.560(6) . y
C3 O13 1.420(5) . y
C3 C4 1.507(6) . y
C4 C5 1.374(6) . y
C4 C9 1.388(6) . y
C5 C6 1.386(6) . y
C6 C7 1.381(7) . y
C7 C8 1.376(7) . y
C8 C9 1.395(6) . y
C9 C10 1.495(6) . y
C10 O11 1.456(5) . y
O11 C12 1.346(5) . y
C12 O14 1.203(5) . y
C15 O16 1.357(5) . y
O16 C17 1.414(5) . y
C17 O18 1.441(5) . y
C17 C21 1.479(6) . y
O18 C19 1.355(5) . y
C19 O22 1.204(5) . y
C19 C20 1.466(6) . y
C20 C21 1.334(6) . y
C20 C23 1.479(6) . 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 O22 0.82 2.03 2.833(5) 165.8 2_456
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26994270
2 PubChem 53349756
