#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/20/8102054.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_8102054
loop_
_publ_author_name
'Tzvetkov, N. T.'
'Neumann, B.'
'Stammler, H.-G.'
'Mattay, J.'
_publ_section_title
;
Crystal structure of (7a'SR)-7a'-prop-2-ynyl-1',2',4',6',7',7a'-hexahydrospiro
[1,3-dioxolan-2,5'-indene], C₁₄H₁₈O₂
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              479
_journal_page_last               480
_journal_volume                  221
_journal_year                    2006
_chemical_formula_moiety         'C14 H18 O2'
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28
_chemical_name_systematic
; 
(7a'SR)-7a'-prop-2-ynyl-1',2',4',6',7',7a'-hexahydrospiro[1,3-dioxolan-2,5'-
indene]
;
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 117.659(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.3990(13)
_cell_length_b                   11.6460(10)
_cell_length_c                   14.8490(12)
_cell_measurement_reflns_used    4256
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.910
_cell_volume                     2358.7(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL-PLUS (1990) [8]'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997) [7]'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997) [7]'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990) [6]'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_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  0.071
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19404
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_correction_T_min  0.9763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0679
_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)+(0.1121P)²+1.9502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1793
_refine_ls_wR_factor_ref         0.2061
_reflns_number_gt                3094
_reflns_number_total             4147
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1886.cff
_cod_data_source_block           niko06
_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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        2358.7(3)
_cod_original_sg_symbol_H-M      P12(1)/c1
_cod_database_code               8102054
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_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.11416(18) 0.2115(2) 0.0765(2) 0.0388(6) Uani 1 4 e d . . .
O2 O 0.07553(18) 0.3672(2) -0.0296(2) 0.0409(7) Uani 1 4 e d . . .
C1 C 0.1566(3) 0.1946(3) 0.0101(3) 0.0437(9) Uani 1 4 e d . . .
H1A H 0.1143 0.1460 -0.0488 0.052 Uiso 1 4 e calc R . .
H1B H 0.2224 0.1592 0.0463 0.052 Uiso 1 4 e calc R . .
C2 C 0.1625(3) 0.3156(3) -0.0223(3) 0.0396(9) Uani 1 4 e d . . .
H2A H 0.2218 0.3551 0.0290 0.048 Uiso 1 4 e calc R . .
H2B H 0.1632 0.3168 -0.0886 0.048 Uiso 1 4 e calc R . .
C3 C 0.0483(3) 0.3078(3) 0.0379(3) 0.0339(8) Uani 1 4 e d . . .
C4 C 0.0614(3) 0.3826(3) 0.1259(3) 0.0343(8) Uani 1 4 e d . . .
H4A H 0.0209 0.4527 0.0998 0.041 Uiso 1 4 e calc R . .
H4B H 0.1309 0.4066 0.1638 0.041 Uiso 1 4 e calc R . .
C5 C 0.0320(3) 0.3199(3) 0.1982(3) 0.0349(8) Uani 1 4 e d . . .
H5A H 0.0413 0.3718 0.2548 0.042 Uiso 1 4 e calc R . .
H5B H 0.0751 0.2524 0.2276 0.042 Uiso 1 4 e calc R . .
C6 C -0.0759(2) 0.2797(3) 0.1433(3) 0.0317(8) Uani 1 4 e d . . .
C7 C -0.1022(3) 0.1886(3) 0.2026(3) 0.0363(8) Uani 1 4 e d . . .
H7A H -0.0422 0.1516 0.2553 0.044 Uiso 1 4 e calc R . .
H7B H -0.1381 0.2243 0.2360 0.044 Uiso 1 4 e calc R . .
C8 C -0.1673(3) 0.1000(3) 0.1227(3) 0.0400(9) Uani 1 4 e d . . .
H8A H -0.1509 0.0208 0.1494 0.048 Uiso 1 4 e calc R . .
H8B H -0.2377 0.1145 0.1007 0.048 Uiso 1 4 e calc R . .
C9 C -0.1429(3) 0.1193(3) 0.0372(3) 0.0355(8) Uani 1 4 e d . . .
H9 H -0.1605 0.0677 -0.0181 0.043 Uiso 1 4 e calc R . .
C10 C -0.0939(2) 0.2164(3) 0.0470(3) 0.0330(8) Uani 1 4 e d . . .
C11 C -0.0576(3) 0.2662(3) -0.0225(3) 0.0354(8) Uani 1 4 e d . . .
H11A H -0.1000 0.3313 -0.0607 0.042 Uiso 1 4 e calc R . .
H11B H -0.0613 0.2072 -0.0722 0.042 Uiso 1 4 e calc R . .
C12 C -0.1468(3) 0.3842(3) 0.1148(3) 0.0347(8) Uani 1 4 e d . . .
H12A H -0.1381 0.4328 0.0649 0.042 Uiso 1 4 e calc R . .
H12B H -0.2153 0.3560 0.0821 0.042 Uiso 1 4 e calc R . .
C13 C -0.1301(3) 0.4537(3) 0.2033(3) 0.0355(8) Uani 1 4 e d . . .
C14 C -0.1137(3) 0.5077(3) 0.2772(3) 0.0388(9) Uani 1 4 e d . . .
H14 H -0.1005 0.5509 0.3364 0.047 Uiso 1 4 e calc R . .
O3 O 0.37401(17) 0.2187(2) 0.46336(18) 0.0352(6) Uani 1 4 e d . . .
O4 O 0.40986(18) 0.3802(2) 0.39845(18) 0.0387(6) Uani 1 4 e d . . .
C15 C 0.3369(3) 0.2025(3) 0.3559(3) 0.0385(9) Uani 1 4 e d . . .
H15A H 0.2729 0.1625 0.3254 0.046 Uiso 1 4 e calc R . .
H15B H 0.3837 0.1590 0.3405 0.046 Uiso 1 4 e calc R . .
C16 C 0.3270(3) 0.3248(3) 0.3199(3) 0.0399(9) Uani 1 4 e d . . .
H16A H 0.3285 0.3296 0.2541 0.048 Uiso 1 4 e calc R . .
H16B H 0.2651 0.3593 0.3122 0.048 Uiso 1 4 e calc R . .
C17 C 0.4401(2) 0.3147(3) 0.4897(3) 0.0328(8) Uani 1 4 e d . . .
C18 C 0.4306(3) 0.3852(3) 0.5708(3) 0.0350(8) Uani 1 4 e d . . .
H18A H 0.3614 0.4088 0.5455 0.042 Uiso 1 4 e calc R . .
H18B H 0.4708 0.4556 0.5846 0.042 Uiso 1 4 e calc R . .
C19 C 0.4639(3) 0.3171(3) 0.6696(3) 0.0342(8) Uani 1 4 e d . . .
H19A H 0.4202 0.2501 0.6569 0.041 Uiso 1 4 e calc R . .
H19B H 0.4584 0.3662 0.7211 0.041 Uiso 1 4 e calc R . .
C20 C 0.5700(2) 0.2755(3) 0.7112(3) 0.0326(8) Uani 1 4 e d . . .
C21 C 0.5981(3) 0.1793(3) 0.7918(3) 0.0352(8) Uani 1 4 e d . . .
H21A H 0.6362 0.2110 0.8612 0.042 Uiso 1 4 e calc R . .
H21B H 0.5387 0.1411 0.7871 0.042 Uiso 1 4 e calc R . .
C22 C 0.6606(3) 0.0942(3) 0.7675(3) 0.0377(9) Uani 1 4 e d . . .
H22A H 0.7314 0.1083 0.8110 0.045 Uiso 1 4 e calc R . .
H22B H 0.6454 0.0139 0.7771 0.045 Uiso 1 4 e calc R . .
C23 C 0.6314(3) 0.1181(3) 0.6581(3) 0.0348(8) Uani 1 4 e d . . .
H23 H 0.6452 0.0683 0.6157 0.042 Uiso 1 4 e calc R . .
C24 C 0.5840(2) 0.2172(3) 0.6273(3) 0.0322(8) Uani 1 4 e d . . .
C25 C 0.5455(2) 0.2736(3) 0.5256(3) 0.0339(8) Uani 1 4 e d . . .
H25A H 0.5472 0.2185 0.4757 0.041 Uiso 1 4 e calc R . .
H25B H 0.5875 0.3399 0.5300 0.041 Uiso 1 4 e calc R . .
C26 C 0.6439(3) 0.3775(3) 0.7541(3) 0.0345(8) Uani 1 4 e d . . .
H26A H 0.7115 0.3469 0.7845 0.041 Uiso 1 4 e calc R . .
H26B H 0.6350 0.4289 0.6974 0.041 Uiso 1 4 e calc R . .
C27 C 0.6316(3) 0.4444(3) 0.8312(3) 0.0370(8) Uani 1 4 e d . . .
C28 C 0.6173(3) 0.4987(3) 0.8908(3) 0.0405(9) Uani 1 4 e d . . .
H28 H 0.6059 0.5420 0.9385 0.049 Uiso 1 4 e 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
C1 O1 C3 107.2(3) . . ?
C2 O2 C3 108.2(3) . . ?
O1 C1 C2 101.9(3) . . ?
O1 C1 H1A 111.4 . . ?
C2 C1 H1A 111.4 . . ?
O1 C1 H1B 111.4 . . ?
C2 C1 H1B 111.4 . . ?
H1A C1 H1B 109.3 . . ?
O2 C2 C1 103.0(3) . . ?
O2 C2 H2A 111.2 . . ?
C1 C2 H2A 111.2 . . ?
O2 C2 H2B 111.2 . . ?
C1 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
O2 C3 O1 105.9(3) . . ?
O2 C3 C4 111.3(3) . . ?
O1 C3 C4 108.6(3) . . ?
O2 C3 C11 108.8(3) . . ?
O1 C3 C11 110.4(3) . . ?
C4 C3 C11 111.6(3) . . ?
C3 C4 C5 111.6(3) . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 111.7(3) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C10 C6 C5 109.1(3) . . ?
C10 C6 C7 102.8(3) . . ?
C5 C6 C7 114.1(3) . . ?
C10 C6 C12 109.0(3) . . ?
C5 C6 C12 110.7(3) . . ?
C7 C6 C12 110.7(3) . . ?
C8 C7 C6 105.6(3) . . ?
C8 C7 H7A 110.6 . . ?
C6 C7 H7A 110.6 . . ?
C8 C7 H7B 110.6 . . ?
C6 C7 H7B 110.6 . . ?
H7A C7 H7B 108.8 . . ?
C9 C8 C7 102.8(3) . . ?
C9 C8 H8A 111.2 . . ?
C7 C8 H8A 111.2 . . ?
C9 C8 H8B 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C10 C9 C8 112.8(3) . . ?
C10 C9 H9 123.6 . . ?
C8 C9 H9 123.6 . . ?
C9 C10 C11 128.9(3) . . ?
C9 C10 C6 111.3(3) . . ?
C11 C10 C6 119.8(3) . . ?
C10 C11 C3 110.9(3) . . ?
C10 C11 H11A 109.5 . . ?
C3 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C6 112.3(3) . . ?
C13 C12 H12A 109.1 . . ?
C6 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C6 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 177.6(4) . . ?
C13 C14 H14 180.0 . . ?
C15 O3 C17 105.7(3) . . ?
C16 O4 C17 107.9(3) . . ?
O3 C15 C16 101.1(3) . . ?
O3 C15 H15A 111.5 . . ?
C16 C15 H15A 111.5 . . ?
O3 C15 H15B 111.5 . . ?
C16 C15 H15B 111.5 . . ?
H15A C15 H15B 109.4 . . ?
O4 C16 C15 103.5(3) . . ?
O4 C16 H16A 111.1 . . ?
C15 C16 H16A 111.1 . . ?
O4 C16 H16B 111.1 . . ?
C15 C16 H16B 111.1 . . ?
H16A C16 H16B 109.0 . . ?
O4 C17 O3 106.2(3) . . ?
O4 C17 C18 110.7(3) . . ?
O3 C17 C18 108.7(3) . . ?
O4 C17 C25 108.7(3) . . ?
O3 C17 C25 110.7(3) . . ?
C18 C17 C25 111.7(3) . . ?
C17 C18 C19 111.5(3) . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C18 C19 C20 111.8(3) . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C24 C20 C19 110.0(3) . . ?
C24 C20 C21 102.5(3) . . ?
C19 C20 C21 113.9(3) . . ?
C24 C20 C26 108.7(3) . . ?
C19 C20 C26 111.2(3) . . ?
C21 C20 C26 110.2(3) . . ?
C22 C21 C20 105.5(3) . . ?
C22 C21 H21A 110.6 . . ?
C20 C21 H21A 110.6 . . ?
C22 C21 H21B 110.6 . . ?
C20 C21 H21B 110.6 . . ?
H21A C21 H21B 108.8 . . ?
C23 C22 C21 103.3(3) . . ?
C23 C22 H22A 111.1 . . ?
C21 C22 H22A 111.1 . . ?
C23 C22 H22B 111.1 . . ?
C21 C22 H22B 111.1 . . ?
H22A C22 H22B 109.1 . . ?
C24 C23 C22 112.0(3) . . ?
C24 C23 H23 124.0 . . ?
C22 C23 H23 124.0 . . ?
C23 C24 C25 128.8(3) . . ?
C23 C24 C20 111.8(3) . . ?
C25 C24 C20 119.4(3) . . ?
C24 C25 C17 110.4(3) . . ?
C24 C25 H25A 109.6 . . ?
C17 C25 H25A 109.6 . . ?
C24 C25 H25B 109.6 . . ?
C17 C25 H25B 109.6 . . ?
H25A C25 H25B 108.1 . . ?
C27 C26 C20 113.0(3) . . ?
C27 C26 H26A 109.0 . . ?
C20 C26 H26A 109.0 . . ?
C27 C26 H26B 109.0 . . ?
C20 C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
C28 C27 C26 177.1(4) . . ?
C27 C28 H28 180.0 . . ?
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
O1 C1 1.427(5) . ?
O1 C3 1.441(4) . ?
O2 C2 1.426(4) . ?
O2 C3 1.431(4) . ?
C1 C2 1.505(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.505(5) . ?
C3 C11 1.531(5) . ?
C4 C5 1.532(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.544(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C10 1.516(5) . ?
C6 C7 1.549(5) . ?
C6 C12 1.557(5) . ?
C7 C8 1.541(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.499(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.328(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.499(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.462(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.185(5) . ?
C14 H14 0.9500 . ?
O3 C15 1.436(4) . ?
O3 C17 1.439(4) . ?
O4 C16 1.423(4) . ?
O4 C17 1.432(4) . ?
C15 C16 1.504(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.519(5) . ?
C17 C25 1.531(5) . ?
C18 C19 1.531(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.532(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C24 1.519(5) . ?
C20 C21 1.547(5) . ?
C20 C26 1.562(5) . ?
C21 C22 1.536(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.498(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.328(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.495(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.466(5) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.189(5) . ?
C28 H28 0.9500 . ?
