#------------------------------------------------------------------------------
#$Date: 2016-02-19 15:29:56 +0100 (vie 19 de feb de 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/33/2003336.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_2003336
loop_
_publ_author_name
'Delanghe, P. H. M.'
'Lautens, M.'
'Lough, A. J.'
_publ_section_title
;
 Two Highly Substituted Methylenecyclopropanes
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              700
_journal_page_last               703
_journal_paper_doi               10.1107/S0108270194011182
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C12 H20 O2'
_chemical_formula_weight         196.3
_chemical_name_systematic
;
 (R*,R*)-α-(1-Methoxy-3-methylenecyclopropyl)-cyclohexanemethanol
;
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 109.65(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.398(2)
_cell_length_b                   10.057(1)
_cell_length_c                   10.177(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      20.3
_cell_volume                     1195.0(3)
_computing_cell_refinement       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'XCAD-4 Software (Siemens, 1993)'
_computing_molecular_graphics    'SHELXTL/PC XP (Sheldrick, 1990)'
_computing_publication_material  'SHELXTL/PC XPUBL (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXTL/PC XLS3 (Sheldrick, 1990)'
_computing_structure_solution    'SHELXTL/PC XS (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       'ω-2θ 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  0.0275
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2512
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        'linear correction for 51% intensity decay'
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.091
_exptl_crystal_description       needle
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.17
_refine_ls_hydrogen_treatment    ' H atoms riding, C-H 0.96\%A, O---H refxyzU'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_obs          0.0511
_refine_ls_shift/esd_max         0.02
_refine_ls_shift/esd_mean        0.00
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F) + 0.0034F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.4120
_refine_ls_wR_factor_obs         0.0799
_reflns_number_observed          1308
_reflns_number_total             2294
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            fg1036.cif
_cod_data_source_block           methoxy
_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_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(F) + 0.0034F^2^]'
was changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w = 1/[\s^2^(F) +
0.0034F^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1194.9(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2003336
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_22
_atom_site_aniso_U_23
_atom_site_aniso_U_33
O(1) 0.042(1) -0.000(1) 0.018(1) 0.063(1) 0.001(1) 0.040(1)
O(2) 0.060(1) 0.001(1) 0.011(1) 0.063(1) 0.011(1) 0.035(1)
C(1) 0.041(1) -0.007(1) 0.016(1) 0.048(1) -0.004(1) 0.037(1)
C(2) 0.070(2) -0.013(1) 0.026(2) 0.050(2) -0.012(1) 0.054(2)
C(3) 0.058(2) -0.000(1) 0.023(1) 0.042(1) 0.005(1) 0.052(2)
C(4) 0.081(2) -0.002(2) 0.016(2) 0.051(2) 0.019(2) 0.083(2)
C(5) 0.049(2) 0.015(2) 0.028(2) 0.119(3) 0.012(2) 0.071(2)
C(6) 0.042(1) 0.001(1) 0.017(1) 0.049(1) 0.007(1) 0.036(1)
C(7) 0.044(1) -0.000(1) 0.019(1) 0.042(1) 0.005(1) 0.043(1)
C(8) 0.067(2) 0.005(1) 0.019(2) 0.051(2) -0.001(1) 0.054(2)
C(9) 0.085(2) 0.002(2) 0.034(2) 0.047(2) -0.009(2) 0.077(2)
C(10) 0.076(2) -0.017(2) 0.032(2) 0.060(2) -0.019(2) 0.069(2)
C(11) 0.064(2) -0.013(1) 0.021(1) 0.066(2) -0.018(2) 0.049(2)
C(12) 0.051(2) -0.003(1) 0.019(1) 0.048(1) -0.005(1) 0.043(1)
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
O(1) 1 0.9029(2) 0.2365(2) 0.5143(2) 0.047(1) Uani d .
O(2) 1 0.8935(2) 0.0961(2) 0.7834(2) 0.054(1) Uani d .
C(1) 1 0.8347(2) 0.2623(2) 0.5989(2) 0.041(1) Uani d .
C(2) 1 0.8545(3) 0.3947(2) 0.6761(3) 0.057(1) Uani d .
C(3) 1 0.7544(3) 0.3725(2) 0.5520(3) 0.050(1) Uani d .
C(4) 1 0.6589(3) 0.4163(3) 0.4622(4) 0.075(1) Uani d .
C(5) 1 1.0208(3) 0.2132(4) 0.5894(3) 0.078(2) Uani d .
C(6) 1 0.8010(2) 0.1422(2) 0.6659(2) 0.042(1) Uani d .
C(7) 1 0.7599(2) 0.0249(2) 0.5662(2) 0.042(1) Uani d .
C(8) 1 0.7112(3) -0.0860(3) 0.6328(3) 0.057(1) Uani d .
C(9) 1 0.6759(3) -0.2072(3) 0.5375(3) 0.068(1) Uani d .
C(10) 1 0.5921(3) -0.1703(3) 0.3952(3) 0.066(1) Uani d .
C(11) 1 0.6386(3) -0.0585(3) 0.3300(3) 0.059(1) Uani d .
C(12) 1 0.6721(2) 0.0622(3) 0.4265(2) 0.047(1) Uani d .
H(2A) 1 0.902(3) 0.148(3) 0.865(4) 0.100(12) Uiso d .
H(2B) 1 0.9141 0.4514 0.6677 0.075(2) Uiso d R
H(2C) 1 0.8432 0.3979 0.7648 0.075(2) Uiso d R
H(4A) 1 0.6137 0.3593 0.3884 0.075(2) Uiso d R
H(4B) 1 0.6339 0.5054 0.4697 0.075(2) Uiso d R
H(5A) 1 1.0604 0.1965 0.5247 0.075(2) Uiso d R
H(5B) 1 1.0531 0.2901 0.6445 0.075(2) Uiso d R
H(5C) 1 1.0284 0.1376 0.6494 0.075(2) Uiso d R
H(6A) 1 0.7396 0.1680 0.6980 0.075(2) Uiso d R
H(7A) 1 0.8255 -0.0106 0.5483 0.075(2) Uiso d R
H(8A) 1 0.6458 -0.0530 0.6530 0.075(2) Uiso d R
H(8B) 1 0.7677 -0.1122 0.7194 0.075(2) Uiso d R
H(9A) 1 0.6414 -0.2719 0.5803 0.075(2) Uiso d R
H(9B) 1 0.7428 -0.2467 0.5264 0.075(2) Uiso d R
H(10A) 1 0.5207 -0.1435 0.4046 0.075(2) Uiso d R
H(10B) 1 0.5778 -0.2468 0.3354 0.075(2) Uiso d R
H(11A) 1 0.5811 -0.0326 0.2440 0.075(2) Uiso d R
H(11B) 1 0.7041 -0.0895 0.3087 0.075(2) Uiso d R
H(12A) 1 0.7036 0.1296 0.3832 0.075(2) Uiso d R
H(12B) 1 0.6052 0.0983 0.4408 0.075(2) Uiso d R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.001
H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000
O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0106 0.006
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(1) O(1) C(5) 114.8(2) yes
O(1) C(1) C(2) 116.6(2) yes
O(1) C(1) C(3) 115.0(2) yes
C(2) C(1) C(3) 58.6(2) yes
O(1) C(1) C(6) 116.0(2) yes
C(2) C(1) C(6) 119.1(2) yes
C(3) C(1) C(6) 119.5(2) yes
C(1) C(2) C(3) 58.5(2) yes
C(1) C(3) C(2) 62.9(2) yes
C(1) C(3) C(4) 147.6(3) yes
C(2) C(3) C(4) 149.5(3) yes
O(2) C(6) C(1) 111.8(2) yes
O(2) C(6) C(7) 107.5(2) yes
C(1) C(6) C(7) 113.5(2) yes
C(6) C(7) C(8) 111.2(2) yes
C(6) C(7) C(12) 113.9(2) yes
C(8) C(7) C(12) 109.2(2) no
C(7) C(8) C(9) 111.8(3) no
C(8) C(9) C(10) 111.7(2) no
C(9) C(10) C(11) 111.1(3) no
C(10) C(11) C(12) 111.7(3) no
C(7) C(12) C(11) 111.1(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(1) 1.418(4) yes
O(1) C(5) 1.422(3) yes
O(2) C(6) 1.427(3) yes
C(1) C(2) 1.523(3) yes
C(1) C(3) 1.459(4) yes
C(1) C(6) 1.514(4) yes
C(2) C(3) 1.460(3) yes
C(3) C(4) 1.305(4) yes
C(6) C(7) 1.527(3) yes
C(7) C(8) 1.531(4) no
C(7) C(12) 1.518(3) no
C(8) C(9) 1.528(4) no
C(9) C(10) 1.517(4) no
C(10) C(11) 1.515(5) no
C(11) C(12) 1.529(4) no
