#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/93/2209302.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2209302
loop_
_publ_author_name
'Mutikainen Ilpo'
'Yli-Kauhaluoma, Jari'
'Salakari, Anja'
_publ_section_title
;
 Spiro[cyclopropane-1,1'-1H-inden]-2'(3'H)-one
;
_journal_coeditor_code           SG2026
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2415
_journal_page_last               o2416
_journal_paper_doi               10.1107/S1600536806017739
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C11 H9 O1'
_chemical_formula_sum            'C11 H9 O'
_chemical_formula_weight         157.18
_chemical_name_systematic
;
Spiro[cyclopropane-1,1'-1H-inden]-2'(3'H)-one'
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 97.340(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9410(10)
_cell_length_b                   6.9960(10)
_cell_length_c                   13.491(2)
_cell_measurement_reflns_used    225
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      18.7
_cell_measurement_theta_min      3.1
_cell_volume                     837.0(2)
_computing_cell_refinement       COLLECT
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        COLLECT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Burla et al.,  2003)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ? ω?'
_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  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4074
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_correction_T_min  0.9768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.259
_refine_ls_extinction_coef       0.061(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0611P)²+0.4406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1380
_reflns_number_gt                1511
_reflns_number_total             2000
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sg2026.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_original_formula_sum        'C11 H9 O1'
_cod_database_code               2209302
_cod_database_fobs_code          2209302
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1A 0.1066(2) 0.2500 0.44049(14) 0.0424(5) Uani d S 1 . 1
C C2A 0.2371(3) 0.2500 0.47846(17) 0.0268(5) Uani d S 1 . 1
C C3A 0.2893(3) 0.2500 0.58846(16) 0.0237(5) Uani d S 1 . 1
C C4A 0.4571(3) 0.2500 0.60005(16) 0.0230(5) Uani d S 1 . 1
C C5A 0.5600(3) 0.2500 0.68629(18) 0.0305(6) Uani d S 1 . 1
H H5AA 0.5262 0.2500 0.7503 0.037 Uiso calc SR 1 . 1
C C6A 0.7131(3) 0.2500 0.6776(2) 0.0378(6) Uani d S 1 . 1
H H6AA 0.7844 0.2500 0.7362 0.045 Uiso calc SR 1 . 1
C C7A 0.7635(3) 0.2500 0.5841(2) 0.0401(7) Uani d S 1 . 1
H H7AA 0.8686 0.2500 0.5793 0.048 Uiso calc SR 1 . 1
C C8A 0.6610(3) 0.2500 0.4981(2) 0.0334(6) Uani d S 1 . 1
H H8AA 0.6956 0.2500 0.4344 0.040 Uiso calc SR 1 . 1
C C9A 0.5072(3) 0.2500 0.50523(17) 0.0244(5) Uani d S 1 . 1
C C10A 0.3759(3) 0.2500 0.42331(17) 0.0276(5) Uani d S 1 . 1
H H10A 0.374(4) 0.370(5) 0.378(3) 0.033 Uiso d P 0.50 A 1
C C11A 0.1948(2) 0.1438(3) 0.65731(14) 0.0342(4) Uani d . 1 . 1
H H11A 0.107(2) 0.077(3) 0.6228(14) 0.041 Uiso d . 1 B 1
H H12A 0.258(2) 0.082(3) 0.7151(15) 0.041 Uiso d . 1 C 1
O O1B 0.3531(2) 0.2500 -0.09557(14) 0.0415(5) Uani d S 1 . 1
C C2B 0.2469(3) 0.2500 -0.04732(17) 0.0263(5) Uani d S 1 . 1
C C3B 0.2597(3) 0.2500 0.06467(17) 0.0234(5) Uani d S 1 . 1
C C4B 0.1034(3) 0.2500 0.09056(16) 0.0234(5) Uani d S 1 . 1
C C5B 0.0554(3) 0.2500 0.18489(19) 0.0312(6) Uani d S 1 . 1
H H5BA 0.1267 0.2500 0.2435 0.037 Uiso calc SR 1 . 1
C C6B -0.0969(3) 0.2500 0.1918(2) 0.0419(7) Uani d S 1 . 1
H H6BA -0.1311 0.2500 0.2557 0.050 Uiso calc SR 1 . 1
C C7B -0.2006(3) 0.2500 0.1063(3) 0.0469(8) Uani d S 1 . 1
H H7BA -0.3053 0.2500 0.1123 0.056 Uiso calc SR 1 . 1
C C8B -0.1539(3) 0.2500 0.0111(2) 0.0378(7) Uani d S 1 . 1
H H8BA -0.2259 0.2500 -0.0471 0.045 Uiso calc SR 1 . 1
C C9B 0.0003(3) 0.2500 0.00338(18) 0.0250(5) Uani d S 1 . 1
C C10B 0.0800(3) 0.2500 -0.08879(17) 0.0271(5) Uani d S 1 . 1
H H10C 0.061(4) 0.132(5) -0.135(3) 0.032 Uiso d P 0.50 D 1
C C11B 0.3903(2) 0.1436(3) 0.12372(14) 0.0338(4) Uani d . 1 . 1
H H11B 0.461(2) 0.080(3) 0.0819(14) 0.041 Uiso d . 1 E 1
H H12B 0.364(2) 0.081(3) 0.1839(14) 0.041 Uiso d . 1 F 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O1A C2A C3A . . 125.4(2)
O1A C2A C10A . . 126.3(2)
C3A C2A C10A . . 108.25(19)
C4A C3A C2A . . 106.65(18)
C4A C3A C11A . 4_565 124.39(16)
C2A C3A C11A . 4_565 118.45(17)
C4A C3A C11A . . 124.39(16)
C2A C3A C11A . . 118.45(17)
C11A C3A C11A 4_565 . 58.28(16)
C5A C4A C9A . . 120.5(2)
C5A C4A C3A . . 129.8(2)
C9A C4A C3A . . 109.74(19)
C4A C5A C6A . . 119.0(2)
C4A C5A H5AA . . 120.5
C6A C5A H5AA . . 120.5
C5A C6A C7A . . 120.8(2)
C5A C6A H6AA . . 119.6
C7A C6A H6AA . . 119.6
C8A C7A C6A . . 120.2(2)
C8A C7A H7AA . . 119.9
C6A C7A H7AA . . 119.9
C7A C8A C9A . . 119.8(2)
C7A C8A H8AA . . 120.1
C9A C8A H8AA . . 120.1
C8A C9A C4A . . 119.7(2)
C8A C9A C10A . . 129.4(2)
C4A C9A C10A . . 111.0(2)
C9A C10A C2A . . 104.38(18)
C9A C10A H10A . . 113(2)
C2A C10A H10A . . 109(2)
C11A C11A C3A 4_565 . 60.86(8)
C11A C11A H11A 4_565 . 118.3(12)
C3A C11A H11A . . 114.5(11)
C11A C11A H12A 4_565 . 115.6(12)
C3A C11A H12A . . 112.7(11)
H11A C11A H12A . . 120.3(17)
O1B C2B C3B . . 125.0(2)
O1B C2B C10B . . 126.7(2)
C3B C2B C10B . . 108.36(19)
C4B C3B C2B . . 106.49(19)
C4B C3B C11B . 4_565 124.04(17)
C2B C3B C11B . 4_565 118.84(17)
C4B C3B C11B . . 124.04(17)
C2B C3B C11B . . 118.84(17)
C11B C3B C11B 4_565 . 58.59(16)
C5B C4B C9B . . 121.4(2)
C5B C4B C3B . . 128.6(2)
C9B C4B C3B . . 109.99(19)
C6B C5B C4B . . 119.0(3)
C6B C5B H5BA . . 120.5
C4B C5B H5BA . . 120.5
C5B C6B C7B . . 120.4(3)
C5B C6B H6BA . . 119.8
C7B C6B H6BA . . 119.8
C6B C7B C8B . . 121.2(2)
C6B C7B H7BA . . 119.4
C8B C7B H7BA . . 119.4
C9B C8B C7B . . 118.8(3)
C9B C8B H8BA . . 120.6
C7B C8B H8BA . . 120.6
C8B C9B C4B . . 119.2(2)
C8B C9B C10B . . 129.5(2)
C4B C9B C10B . . 111.3(2)
C9B C10B C2B . . 103.91(18)
C9B C10B H10C . . 116(2)
C2B C10B H10C . . 107(2)
C11B C11B C3B 4_565 . 60.70(8)
C11B C11B H11B 4_565 . 116.5(12)
C3B C11B H11B . . 114.8(11)
C11B C11B H12B 4_565 . 116.7(12)
C3B C11B H12B . . 113.9(11)
H11B C11B H12B . . 120.1(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1A C2A . 1.213(3)
C2A C3A . 1.498(3)
C2A C10A . 1.527(3)
C3A C4A . 1.489(3)
C3A C11A 4_565 1.526(2)
C3A C11A . 1.526(2)
C4A C5A . 1.388(3)
C4A C9A . 1.408(3)
C5A C6A . 1.389(4)
C5A H5AA . 0.9500
C6A C7A . 1.394(4)
C6A H6AA . 0.9500
C7A C8A . 1.383(4)
C7A H7AA . 0.9500
C8A C9A . 1.391(3)
C8A H8AA . 0.9500
C9A C10A . 1.506(3)
C10A H10A . 1.04(4)
C11A C11A 4_565 1.486(4)
C11A H11A . 0.98(2)
C11A H12A . 1.00(2)
O1B C2B . 1.218(3)
C2B C3B . 1.500(3)
C2B C10B . 1.525(3)
C3B C4B . 1.483(3)
C3B C11B 4_565 1.521(3)
C3B C11B . 1.521(3)
C4B C5B . 1.394(3)
C4B C9B . 1.399(3)
C5B C6B . 1.377(4)
C5B H5BA . 0.9500
C6B C7B . 1.385(5)
C6B H6BA . 0.9500
C7B C8B . 1.400(4)
C7B H7BA . 0.9500
C8B C9B . 1.396(3)
C8B H8BA . 0.9500
C9B C10B . 1.510(3)
C10B H10C . 1.04(4)
C11B C11B 4_565 1.488(4)
C11B H11B . 1.00(2)
C11B H12B . 0.98(2)
