#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/28/2232829.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_2232829
loop_
_publ_author_name
'Yang, Yu'
'Xu, Zhi-kai'
'Yang, Deng-ke'
'Pan, Shao-wu'
'Jiang, La-sheng'
_publ_section_title
;
 Bis{5-[(2-propyn-1-yloxy)methyl]-1,3-phenylene}-32-crown-10
;
_journal_coeditor_code           LD2029
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3244
_journal_paper_doi               10.1107/S1600536811046435
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C36 H48 O12'
_chemical_formula_moiety         'C36 H48 O12'
_chemical_formula_sum            'C36 H48 O12'
_chemical_formula_weight         672.74
_chemical_name_systematic
;
17,35-Bis[(2-propyn-1-yloxy)methyl]-2,5,8,11,14,20,23,26,29,32-
decaoxatricyclo[31.3.1.1^15,19^]octatriaconta-1(37),15,17,19(38),33,35-hexaene
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.213(2)
_cell_angle_beta                 98.658(2)
_cell_angle_gamma                99.226(2)
_cell_formula_units_Z            1
_cell_length_a                   9.2256(13)
_cell_length_b                   9.8561(14)
_cell_length_c                   10.0808(14)
_cell_measurement_temperature    298(2)
_cell_volume                     883.9(2)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4551
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_correction_T_min  0.9650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0419
_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)+(0.0506P)²+0.1259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1126
_reflns_number_gt                2350
_reflns_number_total             3108
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ld2029.cif
_cod_data_source_block           I
_cod_database_code               2232829
_cod_database_fobs_code          2232829
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_symmetry_multiplicity
C C1 0.19258(19) 0.18786(18) 0.55393(17) 0.0405(4) Uani d . 1 1
H H1 0.0968 0.1897 0.5717 0.049 Uiso calc R 1 1
C C2 0.21585(18) 0.15530(18) 0.42298(16) 0.0393(4) Uani d . 1 1
C C3 0.35977(19) 0.15509(19) 0.39575(17) 0.0428(4) Uani d . 1 1
H H3 0.3744 0.1335 0.3068 0.051 Uiso calc R 1 1
C C5 0.45832(19) 0.21882(18) 0.63403(17) 0.0427(4) Uani d . 1 1
H H5 0.5393 0.2404 0.7049 0.051 Uiso calc R 1 1
C C6 0.31507(19) 0.21810(18) 0.65978(16) 0.0392(4) Uani d . 1 1
C C8 -0.13388(19) 0.0898(2) 0.18269(18) 0.0472(5) Uani d . 1 1
H H8A -0.1242 -0.0054 0.1536 0.057 Uiso calc R 1 1
H H8B -0.2380 0.0914 0.1867 0.057 Uiso calc R 1 1
C C7 -0.04096(18) 0.1423(2) 0.32005(17) 0.0456(4) Uani d . 1 1
H H7A -0.0407 0.2406 0.3455 0.055 Uiso calc R 1 1
H H7B -0.0801 0.0923 0.3878 0.055 Uiso calc R 1 1
C C9 -0.1580(2) 0.1224(2) -0.04624(17) 0.0513(5) Uani d . 1 1
H H9A -0.2653 0.1062 -0.0510 0.062 Uiso calc R 1 1
H H9B -0.1291 0.0348 -0.0762 0.062 Uiso calc R 1 1
C C10 0.4014(2) 0.2810(2) 0.89901(17) 0.0519(5) Uani d . 1 1
H H10A 0.4619 0.3688 0.8916 0.062 Uiso calc R 1 1
H H10B 0.4639 0.2107 0.8987 0.062 Uiso calc R 1 1
C C11 0.3400(2) 0.2938(2) 1.02859(17) 0.0520(5) Uani d . 1 1
H H11A 0.2712 0.2091 1.0311 0.062 Uiso calc R 1 1
H H11B 0.4206 0.3065 1.1054 0.062 Uiso calc R 1 1
C C12 0.2334(2) 0.4423(2) 1.17067(16) 0.0492(5) Uani d . 1 1
H H12A 0.3250 0.4829 1.2333 0.059 Uiso calc R 1 1
H H12B 0.1886 0.3588 1.2018 0.059 Uiso calc R 1 1
C C13 0.1296(2) 0.5426(2) 1.16786(17) 0.0513(5) Uani d . 1 1
H H13A 0.0356 0.4998 1.1098 0.062 Uiso calc R 1 1
H H13B 0.1102 0.5687 1.2587 0.062 Uiso calc R 1 1
C C14 0.1140(2) 0.7742(2) 1.13577(19) 0.0553(5) Uani d . 1 1
H H14A 0.1367 0.8184 1.2299 0.066 Uiso calc R 1 1
H H14B 0.0076 0.7388 1.1128 0.066 Uiso calc R 1 1
C C4 0.47982(19) 0.18667(18) 0.49997(17) 0.0408(4) Uani d . 1 1
C C15 0.63517(19) 0.1857(2) 0.46986(19) 0.0492(5) Uani d . 1 1
H H15A 0.6738 0.1108 0.5088 0.059 Uiso calc R 1 1
H H15B 0.6298 0.1666 0.3723 0.059 Uiso calc R 1 1
C C16 0.6984(3) 0.4263(2) 0.4602(2) 0.0663(6) Uani d . 1 1
H H16A 0.7603 0.5112 0.5111 0.080 Uiso calc R 1 1
H H16B 0.5954 0.4319 0.4656 0.080 Uiso calc R 1 1
C C18 0.7341(2) 0.4114(2) 0.2047(2) 0.0671(6) Uani d . 1 1
H H18 0.7476 0.4066 0.1147 0.081 Uiso calc R 1 1
C C17 0.7173(2) 0.4175(2) 0.3175(2) 0.0567(5) Uani d . 1 1
O O6 0.73584(14) 0.31229(15) 0.52126(12) 0.0566(4) Uani d . 1 1
O O1 0.10633(13) 0.11960(14) 0.31046(11) 0.0512(4) Uani d . 1 1
O O3 0.28037(13) 0.24304(13) 0.78669(11) 0.0463(3) Uani d . 1 1
O O4 0.26536(15) 0.40777(14) 1.03810(11) 0.0512(3) Uani d . 1 1
O O5 0.19356(13) 0.66270(14) 1.11802(12) 0.0506(3) Uani d . 1 1
O O2 -0.08593(13) 0.17487(13) 0.08915(11) 0.0490(3) Uani d . 1 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
C2 C1 C6 . . 118.97(15)
C2 C1 H1 . . 120.5
C6 C1 H1 . . 120.5
O1 C2 C1 . . 125.21(15)
O1 C2 C3 . . 114.18(14)
C1 C2 C3 . . 120.60(15)
C4 C3 C2 . . 120.15(15)
C4 C3 H3 . . 119.9
C2 C3 H3 . . 119.9
C6 C5 C4 . . 119.21(15)
C6 C5 H5 . . 120.4
C4 C5 H5 . . 120.4
O3 C6 C5 . . 124.27(15)
O3 C6 C1 . . 114.76(14)
C5 C6 C1 . . 120.95(15)
O2 C8 C7 . . 109.34(15)
O2 C8 H8A . . 109.8
C7 C8 H8A . . 109.8
O2 C8 H8B . . 109.8
C7 C8 H8B . . 109.8
H8A C8 H8B . . 108.3
O1 C7 C8 . . 106.52(14)
O1 C7 H7A . . 110.4
C8 C7 H7A . . 110.4
O1 C7 H7B . . 110.4
C8 C7 H7B . . 110.4
H7A C7 H7B . . 108.6
O2 C9 C14 . 2_566 108.95(16)
O2 C9 H9A . . 109.9
C14 C9 H9A 2_566 . 109.9
O2 C9 H9B . . 109.9
C14 C9 H9B 2_566 . 109.9
H9A C9 H9B . . 108.3
O3 C10 C11 . . 109.13(15)
O3 C10 H10A . . 109.9
C11 C10 H10A . . 109.9
O3 C10 H10B . . 109.9
C11 C10 H10B . . 109.9
H10A C10 H10B . . 108.3
O4 C11 C10 . . 110.25(15)
O4 C11 H11A . . 109.6
C10 C11 H11A . . 109.6
O4 C11 H11B . . 109.6
C10 C11 H11B . . 109.6
H11A C11 H11B . . 108.1
O4 C12 C13 . . 109.57(14)
O4 C12 H12A . . 109.8
C13 C12 H12A . . 109.8
O4 C12 H12B . . 109.8
C13 C12 H12B . . 109.8
H12A C12 H12B . . 108.2
O5 C13 C12 . . 109.56(15)
O5 C13 H13A . . 109.8
C12 C13 H13A . . 109.8
O5 C13 H13B . . 109.8
C12 C13 H13B . . 109.8
H13A C13 H13B . . 108.2
O5 C14 C9 . 2_566 109.25(15)
O5 C14 H14A . . 109.8
C9 C14 H14A 2_566 . 109.8
O5 C14 H14B . . 109.8
C9 C14 H14B 2_566 . 109.8
H14A C14 H14B . . 108.3
C3 C4 C5 . . 120.11(15)
C3 C4 C15 . . 119.87(15)
C5 C4 C15 . . 120.02(16)
O6 C15 C4 . . 113.54(15)
O6 C15 H15A . . 108.9
C4 C15 H15A . . 108.9
O6 C15 H15B . . 108.9
C4 C15 H15B . . 108.9
H15A C15 H15B . . 107.7
O6 C16 C17 . . 113.58(17)
O6 C16 H16A . . 108.8
C17 C16 H16A . . 108.8
O6 C16 H16B . . 108.8
C17 C16 H16B . . 108.8
H16A C16 H16B . . 107.7
C17 C18 H18 . . 180.0
C18 C17 C16 . . 179.1(2)
C16 O6 C15 . . 113.57(15)
C2 O1 C7 . . 119.54(13)
C6 O3 C10 . . 117.49(13)
C11 O4 C12 . . 112.09(13)
C13 O5 C14 . . 112.83(14)
C8 O2 C9 . . 112.47(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.376(2)
C1 C6 . 1.398(2)
C1 H1 . 0.9300
C2 O1 . 1.3682(19)
C2 C3 . 1.396(2)
C3 C4 . 1.373(2)
C3 H3 . 0.9300
C5 C6 . 1.384(2)
C5 C4 . 1.400(2)
C5 H5 . 0.9300
C6 O3 . 1.3672(19)
C8 O2 . 1.412(2)
C8 C7 . 1.497(2)
C8 H8A . 0.9700
C8 H8B . 0.9700
C7 O1 . 1.428(2)
C7 H7A . 0.9700
C7 H7B . 0.9700
C9 O2 . 1.418(2)
C9 C14 2_566 1.492(3)
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 O3 . 1.431(2)
C10 C11 . 1.499(2)
C10 H10A . 0.9700
C10 H10B . 0.9700
C11 O4 . 1.409(2)
C11 H11A . 0.9700
C11 H11B . 0.9700
C12 O4 . 1.423(2)
C12 C13 . 1.482(3)
C12 H12A . 0.9700
C12 H12B . 0.9700
C13 O5 . 1.420(2)
C13 H13A . 0.9700
C13 H13B . 0.9700
C14 O5 . 1.423(2)
C14 C9 2_566 1.492(3)
C14 H14A . 0.9700
C14 H14B . 0.9700
C4 C15 . 1.510(2)
C15 O6 . 1.418(2)
C15 H15A . 0.9700
C15 H15B . 0.9700
C16 O6 . 1.412(3)
C16 C17 . 1.468(3)
C16 H16A . 0.9700
C16 H16B . 0.9700
C18 C17 . 1.167(3)
C18 H18 . 0.9300
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 H13B O6 2_667 0.97 2.49 3.247(2) 135.2
C18 H18 O4 2_666 0.93 2.54 3.203(2) 128.4
C18 H18 O5 2_666 0.93 2.52 3.431(3) 165.5
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
C6 C1 C2 O1 . 177.94(16)
C6 C1 C2 C3 . -1.3(3)
O1 C2 C3 C4 . -178.87(15)
C1 C2 C3 C4 . 0.4(3)
C4 C5 C6 O3 . 177.64(16)
C4 C5 C6 C1 . -1.0(3)
C2 C1 C6 O3 . -177.18(15)
C2 C1 C6 C5 . 1.5(3)
O2 C8 C7 O1 . -67.06(18)
O3 C10 C11 O4 . -67.2(2)
O4 C12 C13 O5 . -57.51(19)
C2 C3 C4 C5 . 0.2(3)
C2 C3 C4 C15 . 179.74(16)
C6 C5 C4 C3 . 0.1(3)
C6 C5 C4 C15 . -179.47(16)
C3 C4 C15 O6 . 125.04(18)
C5 C4 C15 O6 . -55.4(2)
O6 C16 C17 C18 . -90(17)
C17 C16 O6 C15 . -69.0(2)
C4 C15 O6 C16 . -64.9(2)
C1 C2 O1 C7 . 13.2(3)
C3 C2 O1 C7 . -167.59(15)
C8 C7 O1 C2 . -178.61(15)
C5 C6 O3 C10 . 4.2(2)
C1 C6 O3 C10 . -177.17(16)
C11 C10 O3 C6 . -176.06(15)
C10 C11 O4 C12 . -167.39(15)
C13 C12 O4 C11 . -168.70(16)
C12 C13 O5 C14 . -169.02(14)
C9 C14 O5 C13 2_566 -163.09(15)
C7 C8 O2 C9 . 173.50(14)
C14 C9 O2 C8 2_566 173.71(15)
