#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/20/8102055.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_8102055
loop_
_publ_author_name
'Tzvetkov, N. T.'
'Neumann, B.'
'Stammler, H.-G.'
'Mattay, J.'
_publ_section_title
;
Crystal structure of (1aSR,3aRS,7aSR)-3a-but-2-ynyl-1a,2,3,3a,4,5-
hexahydro-1H-cyclopropa[c]inden-6(7H)-one, C₁₄H₁₈O
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              481
_journal_page_last               482
_journal_volume                  221
_journal_year                    2006
_chemical_formula_moiety         'C14 H18 O'
_chemical_formula_sum            'C14 H18 O'
_chemical_formula_weight         202.28
_chemical_name_systematic
; 
(1aSR,3aRS,7aSR)-3a-but-2-ynyl-1a,2,3,3a,4,5-hexahydro-1H-cyclopropa[c]inden-
6(7H)-one, C14H18O 
;
_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                 98.6400(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7800(4)
_cell_length_b                   7.1220(3)
_cell_length_c                   11.7670(7)
_cell_measurement_reflns_used    2134
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.910
_cell_volume                     1141.72(9)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo/Scalepak (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'SHELXTL-PLUS (1990) [4]'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997) [3]'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997) [3]'
_computing_structure_solution    'SHELXS-97 (Sheldrick 1990) [2]'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius kappaCCD'
_diffrn_measurement_method       'CCD; rotation images; thick slices'
_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  0.038
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7865
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9986
_exptl_absorpt_correction_T_min  0.9788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Denzo/Scalepak (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0452
_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)+(0.0640P)²+0.3846P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1251
_reflns_number_gt                1575
_reflns_number_total             2012
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1887.cff
_cod_data_source_block           niko01
_cod_original_sg_symbol_H-M      P12(1)/c1
_cod_database_code               8102055
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 0.52014(9) 0.52242(17) 0.30226(10) 0.0335(3) Uani 1 4 e d . . .
C1 C 0.32690(12) 0.5289(2) 0.07343(14) 0.0243(4) Uani 1 4 e d . . .
C2 C 0.42819(12) 0.4544(2) 0.11819(14) 0.0261(4) Uani 1 4 e d . . .
H2A H 0.4785 0.5305 0.0875 0.031 Uiso 1 4 e calc R . .
H2B H 0.4342 0.3228 0.0931 0.031 Uiso 1 4 e calc R . .
C3 C 0.44358(12) 0.4648(2) 0.24828(14) 0.0253(4) Uani 1 4 e d . . .
C4 C 0.36014(12) 0.3980(3) 0.30873(14) 0.0280(4) Uani 1 4 e d . . .
H4A H 0.3716 0.4445 0.3889 0.034 Uiso 1 4 e calc R . .
H4B H 0.3614 0.2591 0.3116 0.034 Uiso 1 4 e calc R . .
C5 C 0.25724(12) 0.4616(2) 0.25208(14) 0.0270(4) Uani 1 4 e d . . .
H5A H 0.2069 0.3890 0.2851 0.032 Uiso 1 4 e calc R . .
H5B H 0.2483 0.5960 0.2694 0.032 Uiso 1 4 e calc R . .
C6 C 0.24238(11) 0.4337(2) 0.12166(13) 0.0237(4) Uani 1 4 e d . . .
C7 C 0.15075(12) 0.5263(2) 0.05352(15) 0.0309(4) Uani 1 4 e d . . .
H7A H 0.1351 0.6455 0.0902 0.037 Uiso 1 4 e calc R . .
H7B H 0.0933 0.4416 0.0486 0.037 Uiso 1 4 e calc R . .
C8 C 0.17860(14) 0.5628(3) -0.06678(16) 0.0363(5) Uani 1 4 e d . . .
H8A H 0.1642 0.4513 -0.1168 0.044 Uiso 1 4 e calc R . .
H8B H 0.1420 0.6717 -0.1038 0.044 Uiso 1 4 e calc R . .
C9 C 0.28846(13) 0.6028(3) -0.04499(15) 0.0327(4) Uani 1 4 e d . . .
H9 H 0.3286 0.5909 -0.1087 0.039 Uiso 1 4 e calc R . .
C10 C 0.31830(14) 0.7386(2) 0.05243(15) 0.0343(4) Uani 1 4 e d . . .
H10A H 0.2656 0.8068 0.0838 0.041 Uiso 1 4 e calc R . .
H10B H 0.3797 0.8108 0.0522 0.041 Uiso 1 4 e calc R . .
C11 C 0.24196(12) 0.2209(2) 0.09080(14) 0.0245(4) Uani 1 4 e d . . .
H11A H 0.2431 0.2074 0.0073 0.029 Uiso 1 4 e calc R . .
H11B H 0.3022 0.1618 0.1319 0.029 Uiso 1 4 e calc R . .
C12 C 0.15590(12) 0.1215(2) 0.12088(13) 0.0256(4) Uani 1 4 e d . . .
C13 C 0.08404(12) 0.0432(2) 0.14258(14) 0.0271(4) Uani 1 4 e d . . .
C14 C -0.00493(13) -0.0506(3) 0.16868(16) 0.0341(4) Uani 1 4 e d . . .
H14A H -0.0129 -0.0251 0.2486 0.051 Uiso 1 4 e calc R . .
H14B H 0.0009 -0.1863 0.1576 0.051 Uiso 1 4 e calc R . .
H14C H -0.0622 -0.0030 0.1172 0.051 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
C9 C1 C2 128.43(14) . . ?
C9 C1 C10 59.84(11) . . ?
C2 C1 C10 116.61(14) . . ?
C9 C1 C6 108.43(13) . . ?
C2 C1 C6 115.48(13) . . ?
C10 C1 C6 116.89(14) . . ?
C1 C2 C3 108.46(13) . . ?
C1 C2 H2A 110.0 . . ?
C3 C2 H2A 110.0 . . ?
C1 C2 H2B 110.0 . . ?
C3 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
O1 C3 C2 121.47(15) . . ?
O1 C3 C4 121.29(15) . . ?
C2 C3 C4 117.23(14) . . ?
C3 C4 C5 114.72(14) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C6 C5 C4 111.80(13) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C1 C6 C5 108.67(13) . . ?
C1 C6 C7 103.18(13) . . ?
C5 C6 C7 116.27(13) . . ?
C1 C6 C11 108.73(13) . . ?
C5 C6 C11 110.80(13) . . ?
C7 C6 C11 108.75(13) . . ?
C6 C7 C8 104.61(13) . . ?
C6 C7 H7A 110.8 . . ?
C8 C7 H7A 110.8 . . ?
C6 C7 H7B 110.8 . . ?
C8 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
C9 C8 C7 104.76(14) . . ?
C9 C8 H8A 110.8 . . ?
C7 C8 H8A 110.8 . . ?
C9 C8 H8B 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C10 C9 C1 60.29(11) . . ?
C10 C9 C8 113.47(16) . . ?
C1 C9 C8 106.98(14) . . ?
C10 C9 H9 120.4 . . ?
C1 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C1 59.87(11) . . ?
C9 C10 H10A 117.8 . . ?
C1 C10 H10A 117.8 . . ?
C9 C10 H10B 117.8 . . ?
C1 C10 H10B 117.8 . . ?
H10A C10 H10B 114.9 . . ?
C12 C11 C6 112.80(13) . . ?
C12 C11 H11A 109.0 . . ?
C6 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C6 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 177.95(18) . . ?
C12 C13 C14 179.24(19) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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 C3 1.218(2) . ?
C1 C9 1.509(2) . ?
C1 C2 1.512(2) . ?
C1 C10 1.516(2) . ?
C1 C6 1.528(2) . ?
C2 C3 1.515(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.517(2) . ?
C4 C5 1.541(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.530(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.539(2) . ?
C6 C11 1.558(2) . ?
C7 C8 1.543(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.524(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.509(3) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.469(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.197(2) . ?
C13 C14 1.469(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
