#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/41/2224183.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_2224183
loop_
_publ_author_name
'Betz, Richard'
'Klüfers, Peter'
'Mayer, Peter'
_publ_section_title
;
 cis-Cycloheptane-1,2-diol
;
_journal_coeditor_code           DN2506
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3271
_journal_paper_doi               10.1107/S160053680905051X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C7 H14 O2'
_chemical_formula_moiety         'C7 H14 O2'
_chemical_formula_sum            'C7 H14 O2'
_chemical_formula_weight         130.18
_chemical_name_common            cis-Cycloheptane-1,2-diol
_chemical_name_systematic
;
cis-Cycloheptane-1,2-diol
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_cell_angle_alpha                103.861(4)
_cell_angle_beta                 105.685(4)
_cell_angle_gamma                90.189(4)
_cell_formula_units_Z            4
_cell_length_a                   7.4148(5)
_cell_length_b                   8.7629(5)
_cell_length_c                   12.4531(6)
_cell_measurement_reflns_used    8679
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      3.134
_cell_volume                     754.32(8)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2004)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'MONTEL, graded multilayered X-ray optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_sigmaI/netI    0.0621
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4882
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.317
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0693
_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)+(0.1106P)²+0.3333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1875
_refine_ls_wR_factor_ref         0.2070
_reflns_number_gt                1965
_reflns_number_total             2658
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2506.cif
_cod_data_source_block           I
_cod_database_code               2224183
_cod_database_fobs_code          2224183
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 O11 0.2847(2) 0.6535(2) 0.06402(15) 0.0429(5) Uani d . 1 . .
H H11 0.3578 0.6190 0.0241 0.064 Uiso calc R 1 . .
O O12 0.4661(2) 0.36087(19) 0.06017(15) 0.0413(5) Uani d . 1 . .
H H12 0.3830 0.2895 0.0191 0.062 Uiso calc R 1 . .
O O21 0.0359(2) -0.1787(2) -0.05660(15) 0.0419(5) Uani d . 1 . .
H H21 0.1149 -0.2280 -0.0184 0.063 Uiso calc R 1 . .
O O22 0.2163(2) 0.11011(19) -0.06570(15) 0.0425(5) Uani d . 1 . .
H H22 0.1434 0.1044 -0.0253 0.064 Uiso calc R 1 . .
C C11 0.2358(3) 0.5332(3) 0.1133(2) 0.0367(6) Uani d . 1 B .
H H111 0.1420 0.4553 0.0512 0.044 Uiso calc R 1 . .
C C12 0.4071(3) 0.4461(3) 0.1566(2) 0.0361(6) Uani d . 1 . .
H H121 0.3713 0.3695 0.1966 0.043 Uiso calc R 1 . .
C C13 0.5755(4) 0.5519(3) 0.2380(2) 0.0507(7) Uani d . 1 . .
H H131 0.6906 0.4971 0.2328 0.061 Uiso calc R 1 . .
H H132 0.5822 0.6488 0.2111 0.061 Uiso calc R 1 . .
C C14 0.5765(6) 0.5994(5) 0.3625(3) 0.0884(13) Uani d . 1 B .
H H141 0.6132 0.5080 0.3953 0.106 Uiso calc R 1 . .
H H142 0.6776 0.6843 0.4024 0.106 Uiso calc R 1 . .
C C15 0.4085(7) 0.6530(7) 0.3932(3) 0.1032(15) Uani d . 1 . .
H H151 0.4474 0.7281 0.4701 0.124 Uiso calc R 1 A 1
H H152 0.3392 0.5611 0.4007 0.124 Uiso calc R 1 A 1
C C161 0.2784(8) 0.7289(5) 0.3149(3) 0.0689(17) Uani d P 0.817(10) B 1
H H161 0.3523 0.7992 0.2885 0.083 Uiso calc PR 0.817(10) B 1
H H162 0.2013 0.7957 0.3583 0.083 Uiso calc PR 0.817(10) B 1
C C162 0.192(2) 0.626(2) 0.3178(12) 0.053(6) Uani d P 0.183(10) B 2
H H163 0.1397 0.5304 0.3310 0.064 Uiso calc PR 0.183(10) B 2
H H164 0.1271 0.7155 0.3517 0.064 Uiso calc PR 0.183(10) B 2
C C17 0.1397(4) 0.6103(4) 0.2034(3) 0.0571(8) Uani d . 1 . .
H H171 0.0835 0.5270 0.2284 0.069 Uiso calc R 1 B 1
H H172 0.0362 0.6693 0.1680 0.069 Uiso calc R 1 B 1
C C21 0.0931(3) -0.1616(3) -0.1545(2) 0.0347(6) Uani d . 1 . .
H H211 0.1280 -0.2659 -0.1940 0.042 Uiso calc R 1 . .
C C22 0.2640(3) -0.0448(3) -0.1131(2) 0.0355(6) Uani d . 1 . .
H H221 0.3573 -0.0783 -0.0500 0.043 Uiso calc R 1 . .
C C23 0.3614(4) -0.0332(3) -0.2039(3) 0.0536(8) Uani d . 1 . .
H H231 0.4245 -0.1314 -0.2226 0.064 Uiso calc R 1 . .
H H232 0.4600 0.0548 -0.1706 0.064 Uiso calc R 1 . .
C C24 0.2292(6) -0.0064(4) -0.3191(3) 0.0742(10) Uani d . 1 . .
H H241 0.1564 0.0856 -0.2997 0.089 Uiso calc R 1 . .
H H242 0.3084 0.0201 -0.3655 0.089 Uiso calc R 1 . .
C C25 0.0944(6) -0.1437(5) -0.3915(3) 0.0847(12) Uani d . 1 . .
H H251 0.0633 -0.1368 -0.4726 0.102 Uiso calc R 1 . .
H H252 0.1594 -0.2415 -0.3871 0.102 Uiso calc R 1 . .
C C26 -0.0835(6) -0.1586(5) -0.3613(3) 0.0785(11) Uani d . 1 . .
H H261 -0.1345 -0.2698 -0.3925 0.094 Uiso calc R 1 . .
H H262 -0.1743 -0.0940 -0.4015 0.094 Uiso calc R 1 . .
C C27 -0.0755(4) -0.1119(3) -0.2359(2) 0.0484(7) Uani d . 1 . .
H H271 -0.1909 -0.1574 -0.2266 0.058 Uiso calc R 1 . .
H H272 -0.0766 0.0043 -0.2122 0.058 Uiso calc R 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
_geom_angle_publ_flag
C11 O11 H11 . . 109.5 ?
C12 O12 H12 . . 109.5 ?
C21 O21 H21 . . 109.5 ?
C22 O22 H22 . . 109.5 ?
O11 C11 C17 . . 107.3(2) ?
O11 C11 C12 . . 110.63(19) ?
C17 C11 C12 . . 115.3(2) ?
O11 C11 H111 . . 107.8 ?
C17 C11 H111 . . 107.8 ?
C12 C11 H111 . . 107.8 ?
O12 C12 C13 . . 106.8(2) ?
O12 C12 C11 . . 108.94(19) ?
C13 C12 C11 . . 114.6(2) ?
O12 C12 H121 . . 108.8 ?
C13 C12 H121 . . 108.8 ?
C11 C12 H121 . . 108.8 ?
C14 C13 C12 . . 115.8(3) ?
C14 C13 H131 . . 108.3 ?
C12 C13 H131 . . 108.3 ?
C14 C13 H132 . . 108.3 ?
C12 C13 H132 . . 108.3 ?
H131 C13 H132 . . 107.4 ?
C15 C14 C13 . . 120.0(3) ?
C15 C14 H141 . . 107.3 ?
C13 C14 H141 . . 107.3 ?
C15 C14 H142 . . 107.3 ?
C13 C14 H142 . . 107.3 ?
H141 C14 H142 . . 106.9 ?
C14 C15 C161 . . 117.2(4) ?
C14 C15 C162 . . 130.3(6) ?
C161 C15 C162 . . 42.3(7) ?
C14 C15 H151 . . 108.0 ?
C161 C15 H151 . . 108.0 ?
C162 C15 H151 . . 121.1 ?
C14 C15 H152 . . 108.0 ?
C161 C15 H152 . . 108.0 ?
C162 C15 H152 . . 65.7 ?
H151 C15 H152 . . 107.2 ?
C15 C161 C17 . . 115.2(4) ?
C15 C161 H161 . . 108.5 ?
C17 C161 H161 . . 108.5 ?
C15 C161 H162 . . 108.5 ?
C17 C161 H162 . . 108.5 ?
H161 C161 H162 . . 107.5 ?
C17 C162 C15 . . 122.7(11) ?
C17 C162 H163 . . 106.7 ?
C15 C162 H163 . . 106.7 ?
C17 C162 H164 . . 106.7 ?
C15 C162 H164 . . 106.7 ?
H163 C162 H164 . . 106.6 ?
C162 C17 C11 . . 129.7(8) ?
C162 C17 C161 . . 43.2(8) ?
C11 C17 C161 . . 113.6(3) ?
C162 C17 H171 . . 65.7 ?
C11 C17 H171 . . 108.8 ?
C161 C17 H171 . . 108.8 ?
C162 C17 H172 . . 120.6 ?
C11 C17 H172 . . 108.8 ?
C161 C17 H172 . . 108.8 ?
H171 C17 H172 . . 107.7 ?
O21 C21 C22 . . 108.75(19) ?
O21 C21 C27 . . 107.1(2) ?
C22 C21 C27 . . 114.1(2) ?
O21 C21 H211 . . 108.9 ?
C22 C21 H211 . . 108.9 ?
C27 C21 H211 . . 108.9 ?
O22 C22 C21 . . 110.90(18) ?
O22 C22 C23 . . 107.6(2) ?
C21 C22 C23 . . 115.3(2) ?
O22 C22 H221 . . 107.6 ?
C21 C22 H221 . . 107.6 ?
C23 C22 H221 . . 107.6 ?
C22 C23 C24 . . 115.2(2) ?
C22 C23 H231 . . 108.5 ?
C24 C23 H231 . . 108.5 ?
C22 C23 H232 . . 108.5 ?
C24 C23 H232 . . 108.5 ?
H231 C23 H232 . . 107.5 ?
C25 C24 C23 . . 115.1(3) ?
C25 C24 H241 . . 108.5 ?
C23 C24 H241 . . 108.5 ?
C25 C24 H242 . . 108.5 ?
C23 C24 H242 . . 108.5 ?
H241 C24 H242 . . 107.5 ?
C26 C25 C24 . . 116.5(3) ?
C26 C25 H251 . . 108.2 ?
C24 C25 H251 . . 108.2 ?
C26 C25 H252 . . 108.2 ?
C24 C25 H252 . . 108.2 ?
H251 C25 H252 . . 107.3 ?
C25 C26 C27 . . 117.4(3) ?
C25 C26 H261 . . 108.0 ?
C27 C26 H261 . . 108.0 ?
C25 C26 H262 . . 108.0 ?
C27 C26 H262 . . 108.0 ?
H261 C26 H262 . . 107.2 ?
C26 C27 C21 . . 115.9(3) ?
C26 C27 H271 . . 108.3 ?
C21 C27 H271 . . 108.3 ?
C26 C27 H272 . . 108.3 ?
C21 C27 H272 . . 108.3 ?
H271 C27 H272 . . 107.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O11 C11 . 1.431(3) ?
O11 H11 . 0.8400 ?
O12 C12 . 1.431(3) ?
O12 H12 . 0.8400 ?
O21 C21 . 1.434(3) ?
O21 H21 . 0.8400 ?
O22 C22 . 1.431(3) ?
O22 H22 . 0.8400 ?
C11 C17 . 1.515(3) ?
C11 C12 . 1.523(3) ?
C11 H111 . 1.0000 ?
C12 C13 . 1.518(3) ?
C12 H121 . 1.0000 ?
C13 C14 . 1.503(5) ?
C13 H131 . 0.9900 ?
C13 H132 . 0.9900 ?
C14 C15 . 1.447(6) ?
C14 H141 . 0.9900 ?
C14 H142 . 0.9900 ?
C15 C161 . 1.459(6) ?
C15 C162 . 1.609(17) ?
C15 H151 . 0.9900 ?
C15 H152 . 0.9900 ?
C161 C17 . 1.611(6) ?
C161 H161 . 0.9900 ?
C161 H162 . 0.9900 ?
C162 C17 . 1.343(15) ?
C162 H163 . 0.9900 ?
C162 H164 . 0.9900 ?
C17 H171 . 0.9900 ?
C17 H172 . 0.9900 ?
C21 C22 . 1.518(3) ?
C21 C27 . 1.520(3) ?
C21 H211 . 1.0000 ?
C22 C23 . 1.519(3) ?
C22 H221 . 1.0000 ?
C23 C24 . 1.573(5) ?
C23 H231 . 0.9900 ?
C23 H232 . 0.9900 ?
C24 C25 . 1.498(5) ?
C24 H241 . 0.9900 ?
C24 H242 . 0.9900 ?
C25 C26 . 1.480(6) ?
C25 H251 . 0.9900 ?
C25 H252 . 0.9900 ?
C26 C27 . 1.501(4) ?
C26 H261 . 0.9900 ?
C26 H262 . 0.9900 ?
C27 H271 . 0.9900 ?
C27 H272 . 0.9900 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O11 H11 O12 2_665 0.84 1.92 2.697(2) 154.3
O12 H12 O22 . 0.84 1.90 2.733(2) 172.7
O21 H21 O11 1_545 0.84 1.88 2.720(2) 177.5
O22 H22 O21 2 0.84 1.91 2.699(2) 155.7
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O11 C11 C12 O12 . . . . -66.4(2) ?
C17 C11 C12 O12 . . . . 171.6(2) ?
O11 C11 C12 C13 . . . . 53.2(3) ?
C17 C11 C12 C13 . . . . -68.8(3) ?
O12 C12 C13 C14 . . . . -155.2(3) ?
C11 C12 C13 C14 . . . . 84.1(3) ?
C12 C13 C14 C15 . . . . -45.7(5) ?
C13 C14 C15 C161 . . . . -28.3(7) ?
C13 C14 C15 C162 . . . . 20.8(13) ?
C14 C15 C161 C17 . . . . 80.7(6) ?
C162 C15 C161 C17 . . . . -40.4(8) ?
C14 C15 C162 C17 . . . . -31(2) ?
C161 C15 C162 C17 . . . . 56.6(14) ?
C15 C162 C17 C11 . . . . 35(2) ?
C15 C162 C17 C161 . . . . -48.0(11) ?
O11 C11 C17 C162 . . . . -116.9(12) ?
C12 C11 C17 C162 . . . . 6.9(12) ?
O11 C11 C17 C161 . . . . -69.0(3) ?
C12 C11 C17 C161 . . . . 54.7(3) ?
C15 C161 C17 C162 . . . . 49.7(11) ?
C15 C161 C17 C11 . . . . -73.9(4) ?
O21 C21 C22 O22 . . . . -66.9(2) ?
C27 C21 C22 O22 . . . . 52.5(3) ?
O21 C21 C22 C23 . . . . 170.5(2) ?
C27 C21 C22 C23 . . . . -70.1(3) ?
O22 C22 C23 C24 . . . . -73.0(3) ?
C21 C22 C23 C24 . . . . 51.3(3) ?
C22 C23 C24 C25 . . . . -69.2(4) ?
C23 C24 C25 C26 . . . . 84.1(4) ?
C24 C25 C26 C27 . . . . -36.0(5) ?
C25 C26 C27 C21 . . . . -40.9(4) ?
O21 C21 C27 C26 . . . . -152.3(2) ?
C22 C21 C27 C26 . . . . 87.4(3) ?
