#------------------------------------------------------------------------------
#$Date: 2019-10-09 07:03:03 +0300 (Wed, 09 Oct 2019) $
#$Revision: 219178 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/17/2021794.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_2021794
loop_
_publ_author_name
'Shorunov, Sergey V.'
'Bermeshev, Maxim V.'
'Demchuk, Dmitry V.'
'Nelyubina, Yulia V.'
_publ_section_title
;
 Synthesis and structure of 2,4,6-tricyclobutyl-1,3,5-trioxane
;
_journal_coeditor_code           KQ2025
_journal_issue                   11
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              1578
_journal_paper_doi               10.1107/S205698901900896X
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C15 H24 O3'
_chemical_formula_moiety         'C15 H24 O3'
_chemical_formula_sum            'C15 H24 O3'
_chemical_formula_weight         252.34
_chemical_name_systematic
;
2,4,6-Tricyclobutyl-1,3,5-trioxane
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           185
_space_group_name_Hall           'P 6c -2'
_space_group_name_H-M_alt        'P 63 c m'
_symmetry_space_group_name_Hall  'P 6c -2'
_symmetry_space_group_name_H-M   'P 63 c m'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   9.9966(12)
_cell_length_b                   9.9966(12)
_cell_length_c                   7.9461(10)
_cell_measurement_reflns_used    7859
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     687.68(15)
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
SHELXL2014/6 (Sheldrick, 2015b)
;
_computing_publication_material
;
SHELXL2014/6 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2014/6 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII DUO CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7859
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.961
_diffrn_reflns_theta_min         2.353
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       prism
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.223
_refine_ls_abs_structure_details 'Refined as an inversion twin'
_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     35
_refine_ls_number_reflns         671
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0819P)²+0.1148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                645
_reflns_number_total             671
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            kq2025sup1.cif
_cod_data_source_block           Trioxane
_cod_original_cell_volume        687.68(19)
_cod_database_code               2021794
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.984
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'y, x, z'
'x-y, -y, z'
'-x, -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_occupancy
O O1 0.0000 0.13467(13) 0.4774(2) 0.0133(4) Uani d 1
C C1 0.13482(17) 0.13482(17) 0.5351(3) 0.0120(5) Uani d 1
H H1A 0.1384 0.1384 0.6609 0.014 Uiso calc 1
C C2 0.2745(2) 0.2745(2) 0.4645(3) 0.0149(4) Uani d 1
H H2A 0.2716 0.2716 0.3387 0.018 Uiso calc 1
C C3 0.43522(17) 0.31060(18) 0.5281(3) 0.0198(4) Uani d 1
H H3A 0.4938 0.2852 0.4462 0.024 Uiso calc 1
H H3B 0.4334 0.2667 0.6403 0.024 Uiso calc 1
C C4 0.4839(2) 0.4839(2) 0.5319(4) 0.0192(5) Uani d 1
H H4A 0.5420 0.5420 0.4310 0.023 Uiso calc 1
H H4B 0.5377 0.5377 0.6365 0.023 Uiso calc 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
C1 O1 C1 . 2 110.23(18) y
O1 C1 O1 3 . 110.03(17) y
O1 C1 C2 3 . 108.66(11) ?
O1 C1 C2 . . 108.66(11) ?
O1 C1 H1A 3 . 109.8 ?
O1 C1 H1A . . 109.8 ?
C2 C1 H1A . . 109.8 ?
C1 C2 C3 . . 117.97(13) ?
C1 C2 C3 . 10 117.97(13) ?
C3 C2 C3 . 10 88.59(16) y
C1 C2 H2A . . 110.2 ?
C3 C2 H2A . . 110.2 ?
C3 C2 H2A 10 . 110.2 ?
C2 C3 C4 . . 88.62(11) y
C2 C3 H3A . . 113.9 ?
C4 C3 H3A . . 113.9 ?
C2 C3 H3B . . 113.9 ?
C4 C3 H3B . . 113.9 ?
H3A C3 H3B . . 111.1 ?
C3 C4 C3 . 10 88.39(15) ?
C3 C4 H4A . . 113.9 ?
C3 C4 H4A 10 . 113.9 ?
C3 C4 H4B . . 113.9 ?
C3 C4 H4B 10 . 113.9 ?
H4A C4 H4B . . 111.1 ?
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
O1 C1 . 1.4229(13) y
O1 C1 2 1.4230(13) ?
C1 O1 3 1.4229(13) n
C1 C2 . 1.505(3) y
C1 H1A . 1.0000 ?
C2 C3 . 1.545(2) y
C2 C3 10 1.545(2) ?
C2 H2A . 1.0000 ?
C3 C4 . 1.548(2) y
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C3 10 1.548(2) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
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
C1 H1A O1 5 1.00 2.52 3.514(3) 177.1
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_4
_geom_torsion
C1 O1 C1 O1 2 3 58.4(3)
C1 O1 C1 C2 2 . 177.20(10)
O1 C1 C2 C3 3 . -67.9(2)
O1 C1 C2 C3 . . 172.39(15)
O1 C1 C2 C3 3 10 -172.39(15)
O1 C1 C2 C3 . 10 67.9(2)
C1 C2 C3 C4 . . -139.29(18)
C3 C2 C3 C4 10 . -18.09(19)
C2 C3 C4 C3 . 10 18.05(19)
