#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/02/2200219.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_2200219
loop_
_publ_author_name
'Mague, Joel T.'
'Alworth, William L.'
'Foroozesh, Maryam'
_publ_section_title
;
 1-Adamantyl propargyl ether
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o220
_journal_page_last               o221
_journal_paper_doi               10.1107/S1600536801002628
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C13 H18 O'
_chemical_formula_sum            'C13 H18 O'
_chemical_formula_weight         190.27
_chemical_name_systematic
;
 1-(2-propynyloxy)-tricyclo[3.3.1.1^3,7^]decane
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4432(2)
_cell_length_b                   10.9094(2)
_cell_length_c                   13.2137(4)
_cell_measurement_reflns_used    10416
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.5
_cell_volume                     1072.96(5)
_computing_cell_refinement
'DENZO and SCALEPAK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO and SCALEPAK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full .997
_diffrn_measured_fraction_theta_max .997
_diffrn_measurement_device_type
'Nonius KappaCCD (with Oxford Cryosystems Cryostream coller)'
_diffrn_measurement_method       'ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .020
_diffrn_reflns_av_sigmaI/netI    .0333
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10416
_diffrn_reflns_theta_full        30.0
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         3.14
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .072
_exptl_absorpt_correction_T_max  .988
_exptl_absorpt_correction_T_min  .984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(HKL SCALEPAK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          .23
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .17
_refine_diff_density_max         .17
_refine_diff_density_min         -.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          .050
_refine_ls_R_factor_gt           .039
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0367P)²+0.2443P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .092
_reflns_number_gt                1579
_reflns_number_total             1808
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om6008.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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 
;
_cod_database_code               2200219
_cod_database_fobs_code          2200219
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_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
_atom_site_type_symbol
O .01556(14) .82489(9) .81781(8) .0231(2) Uani d . 1 . . O
C1 -.12312(19) .86183(12) .74667(10) .0185(3) Uani d . 1 . . C
C2 -.2046(2) .74062(13) .71162(12) .0259(3) Uani d . 1 . . C
H2A -.2525 .6954 .7707 .034 Uiso calc R 1 . . H
H2B -.1104 .6896 .6797 .034 Uiso calc R 1 . . H
C3 -.3564(2) .76406(14) .63543(11) .0249(3) Uani d . 1 . . C
H3 -.4090 .6842 .6131 .032 Uiso calc R 1 . . H
C4 -.5015(2) .84188(16) .68574(13) .0325(4) Uani d . 1 . . C
H4A -.5527 .7972 .7443 .042 Uiso calc R 1 . . H
H4B -.5997 .8582 .6370 .042 Uiso calc R 1 . . H
C5 -.4197(2) .96290(16) .72125(15) .0377(4) Uani d . 1 . . C
H5 -.5152 1.0137 .7541 .049 Uiso calc R 1 . . H
C6 -.3435(3) 1.03252(16) .63068(17) .0453(5) Uani d . 1 . . C
H6A -.2909 1.1111 .6535 .059 Uiso calc R 1 . . H
H6B -.4408 1.0508 .5819 .059 Uiso calc R 1 . . H
C7 -.1986(3) .95438(18) .57933(13) .0380(4) Uani d . 1 . . C
H7 -.1493 .9996 .5197 .049 Uiso calc R 1 . . H
C8 -.0466(2) .92950(16) .65548(12) .0284(4) Uani d . 1 . . C
H8A .0482 .8793 .6232 .037 Uiso calc R 1 . . H
H8B .0077 1.0079 .6775 .037 Uiso calc R 1 . . H
C9 -.2794(2) .83222(17) .54396(12) .0325(4) Uani d . 1 . . C
H9A -.3757 .8477 .4939 .042 Uiso calc R 1 . . H
H9B -.1855 .7817 .5112 .042 Uiso calc R 1 . . H
C10 -.2688(2) .93883(16) .79773(13) .0297(4) Uani d . 1 . . C
H10A -.2173 1.0176 .8212 .039 Uiso calc R 1 . . H
H10B -.3171 .8946 .8572 .039 Uiso calc R 1 . . H
C11 .1189(2) .92254(14) .85968(12) .0249(3) Uani d . 1 . . C
H11A .0384 .9838 .8914 .032 Uiso calc R 1 . . H
H11B .1885 .9638 .8056 .032 Uiso calc R 1 . . H
C12 .2411(2) .87175(14) .93563(12) .0241(3) Uani d . 1 . . C
C13 .3398(2) .83105(15) .99742(12) .0291(3) Uani d . 1 . . C
H13 .4190 .7984 1.0470 .044 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O .0262(5) .0195(5) .0237(5) -.0017(4) -.0068(4) .0026(4)
C1 .0197(6) .0188(6) .0171(6) .0007(5) -.0009(6) .0018(5)
C2 .0309(8) .0188(7) .0280(7) -.0013(6) -.0047(7) .0003(6)
C3 .0259(7) .0232(7) .0255(7) -.0027(6) -.0033(6) -.0025(6)
C4 .0209(7) .0436(9) .0329(9) -.0010(7) -.0007(7) -.0073(7)
C5 .0277(8) .0368(9) .0487(11) .0134(7) -.0100(8) -.0169(8)
C6 .0497(11) .0247(8) .0615(13) .0021(8) -.0315(11) .0055(8)
C7 .0419(10) .0456(10) .0266(8) -.0171(8) -.0119(8) .0162(8)
C8 .0262(8) .0378(8) .0211(7) -.0092(7) -.0018(6) .0069(6)
C9 .0309(8) .0466(10) .0201(7) -.0038(8) -.0038(7) -.0006(7)
C10 .0258(7) .0350(8) .0282(8) .0039(7) -.0023(7) -.0122(7)
C11 .0265(7) .0219(7) .0264(7) -.0009(6) -.0047(7) .0011(6)
C12 .0255(7) .0234(7) .0233(7) -.0015(6) .0000(6) -.0008(6)
C13 .0303(8) .0295(8) .0276(7) -.0007(7) -.0047(7) .0009(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C11 O C1 115.28(10)
O C1 C8 112.37(11)
O C1 C2 103.78(11)
C8 C1 C2 109.16(12)
O C1 C10 111.76(11)
C8 C1 C10 110.36(13)
C2 C1 C10 109.15(12)
C1 C2 C3 110.31(12)
C4 C3 C9 109.80(14)
C4 C3 C2 109.14(13)
C9 C3 C2 108.86(13)
C3 C4 C5 109.42(13)
C6 C5 C4 109.71(16)
C6 C5 C10 109.23(15)
C4 C5 C10 110.26(15)
C5 C6 C7 109.38(14)
C6 C7 C9 109.99(15)
C6 C7 C8 109.02(15)
C9 C7 C8 109.52(15)
C1 C8 C7 109.15(12)
C3 C9 C7 109.16(13)
C1 C10 C5 108.84(12)
O C11 C12 108.58(12)
C13 C12 C11 179.69(18)
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
O C11 . 1.4258(18) ?
O C1 . 1.4531(16) ?
C1 C8 . 1.5235(19) ?
C1 C2 . 1.5268(19) ?
C1 C10 . 1.528(2) ?
C2 C3 . 1.535(2) ?
C3 C4 . 1.526(2) ?
C3 C9 . 1.530(2) ?
C4 C5 . 1.528(2) ?
C5 C6 . 1.527(3) ?
C5 C10 . 1.534(2) ?
C6 C7 . 1.533(3) ?
C7 C9 . 1.535(3) ?
C7 C8 . 1.538(2) ?
C11 C12 . 1.463(2) ?
C12 C13 . 1.185(2) ?
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
C13 H13 O 3_567 .95 2.35 3.251(2) 158.2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8595475
