#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/92/1519285.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_1519285
loop_
_publ_author_name
'Gelbrich, Thomas'
'Peron, G.'
'Hursthouse, Michael B.'
'Kilburn, Jeremy D.'
_publ_section_title
;
 4,4-Dimethyl-3-methylideneoctahydronaphthalene-2,4a(2H)-diol
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              404
_journal_year                    2000
_chemical_formula_sum            'C13 H22 O2'
_chemical_formula_weight         210.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 98.1620(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9541(2)
_cell_length_b                   7.1843(2)
_cell_length_c                   19.1662(2)
_cell_measurement_reflns_used    9801
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.58
_cell_measurement_theta_min      2.91
_cell_volume                     1220.45(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0790
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4854
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0490
_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)+(0.0495P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                1280
_reflns_number_total             2160
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-404.cif
_cod_data_source_block           s92
_cod_depositor_comments
;
Citation :
Gelbrich, Thomas and Peron, G. and Hursthouse, Michael B. and 
Kilburn, Jeremy D. (2000) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/404)

More at:
http://ecrystals.chem.soton.ac.uk/404/
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1519285
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.34516(13) 0.67407(15) 0.18947(6) 0.0397(4) Uani 1 1 d . . .
H1O H 0.3221 0.5644 0.1829 0.087(8) Uiso 1 1 calc R . .
O2 O 0.25388(14) 1.30053(14) 0.18670(8) 0.0520(4) Uani 1 1 d . . .
H2O H 0.2352 1.2655 0.2252 0.097(9) Uiso 1 1 calc R . .
C1 C 0.38516(18) 0.7525(2) 0.12545(9) 0.0328(4) Uani 1 1 d . . .
C2 C 0.23953(19) 0.8421(2) 0.08391(9) 0.0394(5) Uani 1 1 d . . .
C3 C 0.1873(2) 1.0008(2) 0.12739(9) 0.0375(5) Uani 1 1 d . . .
C4 C 0.3063(2) 1.1470(2) 0.14977(10) 0.0408(5) Uani 1 1 d . . .
H4 H 0.3376 1.1971 0.1065 0.039(5) Uiso 1 1 calc R . .
C5 C 0.4444(2) 1.0560(2) 0.19106(10) 0.0410(5) Uani 1 1 d . . .
H5A H 0.4180 1.0051 0.2346 0.037(5) Uiso 1 1 calc R . .
H5B H 0.5220 1.1493 0.2032 0.051(5) Uiso 1 1 calc R . .
C6 C 0.50584(19) 0.9016(2) 0.14914(10) 0.0380(5) Uani 1 1 d . . .
H6 H 0.5328 0.9588 0.1062 0.037(5) Uiso 1 1 calc R . .
C7 C 0.6503(2) 0.8167(3) 0.18843(11) 0.0506(6) Uani 1 1 d . . .
H7A H 0.7250 0.9141 0.1994 0.069(6) Uiso 1 1 calc R . .
H7B H 0.6291 0.7639 0.2325 0.048(5) Uiso 1 1 calc R . .
C8 C 0.7143(2) 0.6664(3) 0.14558(12) 0.0557(6) Uani 1 1 d . . .
H8A H 0.7453 0.7209 0.1036 0.061(6) Uiso 1 1 calc R . .
H8B H 0.8024 0.6112 0.1732 0.057(6) Uiso 1 1 calc R . .
C9 C 0.5965(2) 0.5176(2) 0.12475(12) 0.0535(6) Uani 1 1 d . . .
H9A H 0.5717 0.4564 0.1667 0.056(6) Uiso 1 1 calc R . .
H9B H 0.6369 0.4247 0.0958 0.063(6) Uiso 1 1 calc R . .
C10 C 0.4544(2) 0.6022(2) 0.08398(10) 0.0436(5) Uani 1 1 d . . .
H10A H 0.3806 0.5044 0.0717 0.037(4) Uiso 1 1 calc R . .
H10B H 0.4787 0.6555 0.0405 0.048(5) Uiso 1 1 calc R . .
C11 C 0.1162(2) 0.6933(3) 0.06737(13) 0.0614(6) Uani 1 1 d . . .
H11A H 0.1508 0.5980 0.0384 0.061(6) Uiso 1 1 calc R . .
H11B H 0.0266 0.7497 0.0428 0.066(6) Uiso 1 1 calc R . .
H11C H 0.0940 0.6393 0.1106 0.073(8) Uiso 1 1 calc R . .
C12 C 0.2689(3) 0.9229(3) 0.01225(10) 0.0578(6) Uani 1 1 d . . .
H12A H 0.2905 0.8233 -0.0182 0.075(7) Uiso 1 1 calc R . .
H12B H 0.3534 1.0064 0.0196 0.091(9) Uiso 1 1 calc R . .
H12C H 0.1811 0.9892 -0.0092 0.094(8) Uiso 1 1 calc R . .
C13 C 0.0515(3) 1.0149(3) 0.14564(12) 0.0586(6) Uani 1 1 d . . .
H13B H 0.0277 1.1154 0.1726 0.055(6) Uiso 1 1 calc R . .
H13A H -0.0207 0.9243 0.1316 0.058(6) Uiso 1 1 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
C1 O1 H1O 109.5 . .
C4 O2 H2O 109.5 . .
O1 C1 C10 109.60(13) . .
O1 C1 C6 105.62(13) . .
C10 C1 C6 109.00(13) . .
O1 C1 C2 107.69(12) . .
C10 C1 C2 113.40(14) . .
C6 C1 C2 111.22(13) . .
C3 C2 C11 111.45(15) . .
C3 C2 C12 107.97(14) . .
C11 C2 C12 106.59(17) . .
C3 C2 C1 109.10(14) . .
C11 C2 C1 109.94(14) . .
C12 C2 C1 111.77(15) . .
C13 C3 C4 120.72(18) . .
C13 C3 C2 124.70(17) . .
C4 C3 C2 114.57(15) . .
O2 C4 C3 114.17(15) . .
O2 C4 C5 112.06(15) . .
C3 C4 C5 109.70(13) . .
O2 C4 H4 106.8 . .
C3 C4 H4 106.8 . .
C5 C4 H4 106.8 . .
C4 C5 C6 111.62(15) . .
C4 C5 H5A 109.3 . .
C6 C5 H5A 109.3 . .
C4 C5 H5B 109.3 . .
C6 C5 H5B 109.3 . .
H5A C5 H5B 108.0 . .
C5 C6 C7 112.08(15) . .
C5 C6 C1 111.81(14) . .
C7 C6 C1 112.11(14) . .
C5 C6 H6 106.8 . .
C7 C6 H6 106.8 . .
C1 C6 H6 106.8 . .
C8 C7 C6 112.07(17) . .
C8 C7 H7A 109.2 . .
C6 C7 H7A 109.2 . .
C8 C7 H7B 109.2 . .
C6 C7 H7B 109.2 . .
H7A C7 H7B 107.9 . .
C9 C8 C7 110.02(16) . .
C9 C8 H8A 109.7 . .
C7 C8 H8A 109.7 . .
C9 C8 H8B 109.7 . .
C7 C8 H8B 109.7 . .
H8A C8 H8B 108.2 . .
C8 C9 C10 110.69(15) . .
C8 C9 H9A 109.5 . .
C10 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
C10 C9 H9B 109.5 . .
H9A C9 H9B 108.1 . .
C9 C10 C1 112.81(16) . .
C9 C10 H10A 109.0 . .
C1 C10 H10A 109.0 . .
C9 C10 H10B 109.0 . .
C1 C10 H10B 109.0 . .
H10A C10 H10B 107.8 . .
C2 C11 H11A 109.5 . .
C2 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C2 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C2 C12 H12A 109.5 . .
C2 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C2 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C3 C13 H13B 120.0 . .
C3 C13 H13A 120.0 . .
H13B C13 H13A 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.4410(17) .
O1 H1O 0.8200 .
O2 C4 1.4253(18) .
O2 H2O 0.8200 .
C1 C10 1.524(2) .
C1 C6 1.543(2) .
C1 C2 1.566(2) .
C2 C3 1.524(2) .
C2 C11 1.538(2) .
C2 C12 1.548(2) .
C3 C13 1.316(2) .
C3 C4 1.514(2) .
C4 C5 1.518(2) .
C4 H4 0.9800 .
C5 C6 1.518(2) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.528(2) .
C6 H6 0.9800 .
C7 C8 1.517(2) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.516(2) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.522(3) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 H13B 0.9300 .
C13 H13A 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O2 0.82 2.00 2.8037(15) 168.3 1_545
O2 H2O O1 0.82 1.99 2.8004(18) 170.4 2
