#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/10/7151027.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_7151027
loop_
_publ_author_name
'Ramachary, Dhevalapally B.'
'Reddy, Y. Vijayendar'
'Kishor, Mamillapalli'
_publ_section_title
;
 Multi-catalysis reactions: direct organocatalytic sequential one-pot
 synthesis of highly functionalized cyclopenta[b]chromen-1-ones
;
_journal_issue                   22
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              4188
_journal_page_last               4197
_journal_paper_doi               10.1039/b812551a
_journal_volume                  6
_journal_year                    2008
_chemical_formula_sum            'C12 H10 O2'
_chemical_formula_weight         186.20
_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_method           SHELXL-97
_cell_angle_alpha                97.609(6)
_cell_angle_beta                 103.781(6)
_cell_angle_gamma                106.000(6)
_cell_formula_units_Z            2
_cell_length_a                   6.589(3)
_cell_length_b                   7.550(3)
_cell_length_c                   9.691(4)
_cell_measurement_temperature    298(2)
_cell_volume                     439.8(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4346
_diffrn_reflns_theta_full        25.90
_diffrn_reflns_theta_max         25.90
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_correction_T_min  0.9611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.085(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0399
_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)+(0.0556P)²+0.0645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                1394
_reflns_number_total             1678
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b812551a.txt
_cod_data_source_block           dbr50_m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_cell_volume        439.9(3)
_cod_original_sg_symbol_H-M      p-1
_cod_database_code               7151027
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6727(2) 0.50665(19) 0.73855(15) 0.0420(4) Uani 1 1 d . . .
C2 C 0.8019(2) 0.4915(2) 0.63028(16) 0.0501(4) Uani 1 1 d . . .
H2A H 0.7443 0.5374 0.5453 0.060 Uiso 1 1 calc R . .
H2B H 0.7939 0.3616 0.5994 0.060 Uiso 1 1 calc R . .
C3 C 1.0389(2) 0.6130(2) 0.70955(15) 0.0473(4) Uani 1 1 d . . .
H3A H 1.1387 0.5391 0.7141 0.057 Uiso 1 1 calc R . .
H3B H 1.0874 0.7167 0.6631 0.057 Uiso 1 1 calc R . .
C4 C 1.3750(2) 0.98055(19) 1.19264(16) 0.0468(4) Uani 1 1 d . . .
H4 H 1.5074 1.0102 1.1690 0.056 Uiso 1 1 calc R . .
C5 C 1.3679(2) 1.0544(2) 1.32752(16) 0.0527(4) Uani 1 1 d . . .
H5 H 1.4957 1.1352 1.3960 0.063 Uiso 1 1 calc R . .
C6 C 1.1717(3) 1.0091(2) 1.36173(16) 0.0538(4) Uani 1 1 d . . .
H6 H 1.1669 1.0592 1.4534 0.065 Uiso 1 1 calc R . .
C7 C 0.9826(2) 0.8898(2) 1.26065(16) 0.0473(4) Uani 1 1 d . . .
H7 H 0.8512 0.8599 1.2855 0.057 Uiso 1 1 calc R . .
C8 C 0.7752(2) 0.68203(19) 1.01197(15) 0.0418(3) Uani 1 1 d . . .
H8A H 0.7172 0.5713 1.0489 0.050 Uiso 1 1 calc R . .
H8B H 0.6647 0.7452 0.9944 0.050 Uiso 1 1 calc R . .
C9 C 0.9826(2) 0.81266(18) 1.12233(14) 0.0377(3) Uani 1 1 d . . .
C10 C 1.1838(2) 0.86169(18) 1.09210(14) 0.0386(3) Uani 1 1 d . . .
C11 C 1.0235(2) 0.68183(18) 0.85610(15) 0.0391(3) Uani 1 1 d . . .
C12 C 0.8237(2) 0.62484(18) 0.87448(14) 0.0372(3) Uani 1 1 d . . .
O1 O 1.20850(14) 0.79587(14) 0.95747(10) 0.0470(3) Uani 1 1 d . . .
O2 O 0.47515(16) 0.43152(15) 0.71375(11) 0.0592(4) Uani 1 1 d . . .
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
O2 C1 C12 126.54(13) . . ?
O2 C1 C2 125.10(13) . . ?
C12 C1 C2 108.36(12) . . ?
C1 C2 C3 105.78(12) . . ?
C1 C2 H2A 110.6 . . ?
C3 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
C3 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
C11 C3 C2 102.17(11) . . ?
C11 C3 H3A 111.3 . . ?
C2 C3 H3A 111.3 . . ?
C11 C3 H3B 111.3 . . ?
C2 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C5 C4 C10 119.32(14) . . ?
C5 C4 H4 120.3 . . ?
C10 C4 H4 120.3 . . ?
C4 C5 C6 119.94(13) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 120.12(14) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C9 121.72(14) . . ?
C6 C7 H7 119.1 . . ?
C9 C7 H7 119.1 . . ?
C12 C8 C9 109.70(11) . . ?
C12 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C12 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C7 116.40(13) . . ?
C10 C9 C8 122.03(12) . . ?
C7 C9 C8 121.57(12) . . ?
C4 C10 C9 122.51(13) . . ?
C4 C10 O1 114.76(12) . . ?
C9 C10 O1 122.74(12) . . ?
C12 C11 O1 125.86(13) . . ?
C12 C11 C3 115.76(12) . . ?
O1 C11 C3 118.37(12) . . ?
C11 C12 C1 107.91(12) . . ?
C11 C12 C8 123.54(12) . . ?
C1 C12 C8 128.52(12) . . ?
C11 O1 C10 116.10(10) . . ?
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 O2 1.2172(17) . ?
C1 C12 1.4478(19) . ?
C1 C2 1.512(2) . ?
C2 C3 1.524(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C11 1.483(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.368(2) . ?
C4 C10 1.3792(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(2) . ?
C6 H6 0.9300 . ?
C7 C9 1.389(2) . ?
C7 H7 0.9300 . ?
C8 C12 1.4799(19) . ?
C8 C9 1.5052(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.3868(19) . ?
C10 O1 1.3964(16) . ?
C11 C12 1.3309(19) . ?
C11 O1 1.3487(17) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25939219
2 PubChem 25171989
