#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202205.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_2202205
loop_
_publ_author_name
'Ravishankar, T.'
'Chinnakali, K.'
'Rajakumar, P.'
'Murali, V.'
'Usman, Anwar'
'Fun, Hoong-Kun'
_publ_section_title
;
 7,16-Dioxatetracyclo[16.2^4,5^.2^21,22^.2^23,24^.0^9,14^]tetracosa-1,3,5,9,11,13,17,19,21,23-decaene
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o293
_journal_page_last               o295
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C22 H18 O2'
_chemical_formula_moiety         'C22 H18 O2'
_chemical_formula_sum            'C22 H18 O2'
_chemical_formula_weight         314.36
_chemical_name_systematic
;
7,16-dioxatetracyclo(16.2^4,5^.2^21,22^.2^23,24^.0^9,14^)-tetracosa-
1,3,5,9,11,13,17,19,21,23-decaene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.4630(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3086(7)
_cell_length_b                   5.8168(3)
_cell_length_c                   20.8145(11)
_cell_measurement_reflns_used    3501
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      3.49
_cell_volume                     1604.00(15)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
;
Siemens SMART CCD area-detector
;
_diffrn_measurement_method       \w
_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  0.1194
_diffrn_reflns_av_sigmaI/netI    0.1547
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8283
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         3.49
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.325
_refine_ls_extinction_coef       0.061(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1329
_refine_ls_R_factor_gt           0.0772
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.071P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1772
_refine_ls_wR_factor_ref         0.1964
_reflns_number_gt                1910
_reflns_number_total             3288
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    wn6138.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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               2202205
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_occupancy
_atom_site_type_symbol
O1 0.44819(17) 0.6278(4) 0.07423(11) 0.0266(6) Uani d 1 O
O2 0.05225(17) 0.6426(4) 0.06238(11) 0.0271(6) Uani d 1 O
C1 0.3706(3) 0.5309(6) 0.02856(17) 0.0235(8) Uani d 1 C
H1A 0.333(3) 0.417(6) 0.0523(17) 0.028 Uiso d 1 H
H1B 0.411(3) 0.457(6) -0.0062(17) 0.028 Uiso d 1 H
C2 0.3014(3) 0.7142(6) -0.00255(15) 0.0210(8) Uani d 1 C
C3 0.3468(3) 0.8864(7) -0.03696(17) 0.0306(9) Uani d 1 C
H3 0.417(3) 0.885(6) -0.0379(17) 0.037 Uiso d 1 H
C4 0.2910(3) 1.0539(7) -0.07133(18) 0.0359(10) Uani d 1 C
H4 0.329(3) 1.176(6) -0.0994(18) 0.043 Uiso d 1 H
C5 0.1857(3) 1.0530(7) -0.07216(18) 0.0341(10) Uani d 1 C
H5 0.140(3) 1.182(7) -0.0942(18) 0.041 Uiso d 1 H
C6 0.1394(3) 0.8845(6) -0.03737(17) 0.0293(9) Uani d 1 C
H6 0.069(3) 0.903(6) -0.0376(17) 0.035 Uiso d 1 H
C7 0.1947(3) 0.7169(6) -0.00186(15) 0.0218(8) Uani d 1 C
C8 0.1374(3) 0.5428(6) 0.03407(18) 0.0249(8) Uani d 1 C
H8A 0.104(3) 0.422(6) 0.0036(17) 0.030 Uiso d 1 H
H8B 0.178(3) 0.469(6) 0.0708(17) 0.030 Uiso d 1 H
C9 0.0785(3) 0.7317(6) 0.12410(15) 0.0213(8) Uani d 1 C
C10 0.0577(3) 0.6010(6) 0.17722(17) 0.0233(8) Uani d 1 C
H10 0.018(3) 0.451(6) 0.1703(16) 0.028 Uiso d 1 H
C11 0.0917(3) 0.6759(6) 0.23900(17) 0.0256(9) Uani d 1 C
H11 0.083(3) 0.571(6) 0.2750(17) 0.031 Uiso d 1 H
C12 0.1481(3) 0.8759(6) 0.24788(16) 0.0228(8) Uani d 1 C
C13 0.1593(3) 1.0152(6) 0.19415(17) 0.0246(8) Uani d 1 C
H13 0.204(3) 1.168(6) 0.2002(16) 0.030 Uiso d 1 H
C14 0.1247(3) 0.9449(6) 0.13233(17) 0.0245(8) Uani d 1 C
H14 0.139(3) 1.034(6) 0.0921(17) 0.029 Uiso d 1 H
C15 0.2118(3) 0.9287(6) 0.30965(17) 0.0274(9) Uani d 1 C
H15 0.184(3) 0.978(6) 0.3495(18) 0.033 Uiso d 1 H
C16 0.3114(3) 0.9090(6) 0.31151(17) 0.0242(8) Uani d 1 C
H16 0.355(3) 0.962(6) 0.3524(17) 0.029 Uiso d 1 H
C17 0.3599(3) 0.8278(5) 0.25381(15) 0.0192(8) Uani d 1 C
C18 0.4207(3) 0.9665(6) 0.21956(16) 0.0202(8) Uani d 1 C
H18 0.441(3) 1.122(6) 0.2371(16) 0.024 Uiso d 1 H
C19 0.4489(3) 0.8991(6) 0.15960(16) 0.0214(8) Uani d 1 C
H19 0.486(3) 0.991(6) 0.1353(16) 0.026 Uiso d 1 H
C20 0.4174(2) 0.6889(6) 0.13388(15) 0.0188(7) Uani d 1 C
C21 0.3640(3) 0.5395(6) 0.16992(16) 0.0211(8) Uani d 1 C
H21 0.345(3) 0.392(6) 0.1529(16) 0.025 Uiso d 1 H
C22 0.3350(3) 0.6094(6) 0.22915(15) 0.0198(8) Uani d 1 C
H22 0.287(3) 0.502(6) 0.2543(15) 0.024 Uiso d 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
O1 0.0172(13) 0.0413(15) 0.0221(13) -0.0017(12) 0.0059(10) -0.0079(11)
O2 0.0188(13) 0.0378(15) 0.0244(13) -0.0001(12) 0.0004(10) -0.0057(11)
C1 0.0192(19) 0.030(2) 0.0218(19) -0.0029(17) 0.0033(15) -0.0067(16)
C2 0.0214(19) 0.0263(19) 0.0149(17) -0.0012(16) 0.0004(14) -0.0064(14)
C3 0.033(2) 0.037(2) 0.0233(19) -0.004(2) 0.0092(17) -0.0055(17)
C4 0.056(3) 0.028(2) 0.025(2) -0.004(2) 0.0063(19) 0.0002(17)
C5 0.048(3) 0.030(2) 0.024(2) 0.009(2) 0.0049(18) 0.0012(17)
C6 0.032(2) 0.033(2) 0.024(2) 0.0095(19) 0.0060(17) -0.0004(16)
C7 0.027(2) 0.0226(19) 0.0160(17) 0.0011(16) 0.0028(14) -0.0057(14)
C8 0.0213(19) 0.026(2) 0.028(2) -0.0004(17) 0.0042(16) -0.0039(16)
C9 0.0188(18) 0.0254(19) 0.0200(18) -0.0011(15) 0.0025(14) -0.0048(15)
C10 0.0173(18) 0.0237(19) 0.030(2) -0.0039(16) 0.0066(15) 0.0005(16)
C11 0.028(2) 0.025(2) 0.026(2) 0.0006(17) 0.0118(16) -0.0013(16)
C12 0.0190(18) 0.0271(19) 0.0233(18) 0.0047(16) 0.0066(15) -0.0080(15)
C13 0.024(2) 0.0177(18) 0.032(2) 0.0002(16) 0.0040(16) -0.0026(15)
C14 0.026(2) 0.0231(19) 0.0244(19) 0.0002(17) 0.0038(16) 0.0023(15)
C15 0.032(2) 0.030(2) 0.0206(19) -0.0028(18) 0.0064(16) -0.0060(16)
C16 0.030(2) 0.024(2) 0.0187(18) 0.0010(17) 0.0012(15) -0.0032(15)
C17 0.0218(18) 0.0162(17) 0.0190(17) 0.0023(15) -0.0016(14) 0.0002(13)
C18 0.0191(18) 0.0182(18) 0.0230(18) 0.0024(15) -0.0001(14) -0.0012(15)
C19 0.0197(18) 0.0215(19) 0.0235(19) -0.0027(16) 0.0041(15) 0.0030(15)
C20 0.0131(16) 0.0261(19) 0.0175(17) 0.0052(15) 0.0028(13) -0.0003(14)
C21 0.0202(18) 0.0170(17) 0.0258(19) 0.0036(15) 0.0001(15) 0.0003(15)
C22 0.0212(18) 0.0182(18) 0.0201(18) 0.0016(15) 0.0019(14) 0.0045(14)
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_publ_flag
C20 O1 C1 115.6(2) ?
C9 O2 C8 112.7(3) ?
O1 C1 C2 111.9(3) y
O1 C1 H1A 107(2) ?
C2 C1 H1A 112(2) ?
O1 C1 H1B 104(2) ?
C2 C1 H1B 109(2) ?
H1A C1 H1B 113(3) ?
C3 C2 C7 118.4(3) ?
C3 C2 C1 116.7(3) y
C7 C2 C1 124.8(3) y
C4 C3 C2 122.2(4) ?
C4 C3 H3 119(2) ?
C2 C3 H3 119(2) ?
C3 C4 C5 119.4(4) ?
C3 C4 H4 120(2) ?
C5 C4 H4 121(2) ?
C6 C5 C4 119.2(4) ?
C6 C5 H5 117(2) ?
C4 C5 H5 123(2) ?
C7 C6 C5 122.0(4) ?
C7 C6 H6 124(2) ?
C5 C6 H6 114(2) ?
C6 C7 C2 118.8(3) ?
C6 C7 C8 117.8(3) y
C2 C7 C8 123.4(3) y
O2 C8 C7 112.7(3) y
O2 C8 H8A 103(2) ?
C7 C8 H8A 111(2) ?
O2 C8 H8B 104(2) ?
C7 C8 H8B 114(2) ?
H8A C8 H8B 111(3) ?
C14 C9 C10 120.6(3) ?
C14 C9 O2 120.9(3) ?
C10 C9 O2 118.4(3) ?
C9 C10 C11 119.4(3) ?
C9 C10 H10 119.6(19) ?
C11 C10 H10 121.0(19) ?
C12 C11 C10 120.7(3) ?
C12 C11 H11 121(2) ?
C10 C11 H11 117(2) ?
C11 C12 C13 118.4(3) ?
C11 C12 C15 122.6(3) ?
C13 C12 C15 118.1(3) ?
C14 C13 C12 121.3(3) ?
C14 C13 H13 119.0(18) ?
C12 C13 H13 119.1(18) ?
C13 C14 C9 118.8(3) ?
C13 C14 H14 122.7(19) ?
C9 C14 H14 118.0(19) ?
C16 C15 C12 119.2(3) ?
C16 C15 H15 117(2) ?
C12 C15 H15 124(2) ?
C15 C16 C17 120.7(3) ?
C15 C16 H16 118.9(19) ?
C17 C16 H16 120.2(19) ?
C18 C17 C22 118.0(3) ?
C18 C17 C16 123.2(3) ?
C22 C17 C16 118.5(3) ?
C17 C18 C19 121.1(3) ?
C17 C18 H18 119.1(19) ?
C19 C18 H18 119.7(19) ?
C20 C19 C18 119.9(3) ?
C20 C19 H19 118(2) ?
C18 C19 H19 123(2) ?
C19 C20 C21 119.7(3) ?
C19 C20 O1 117.9(3) y
C21 C20 O1 122.2(3) y
C20 C21 C22 119.8(3) ?
C20 C21 H21 120(2) ?
C22 C21 H21 120(2) ?
C21 C22 C17 121.1(3) ?
C21 C22 H22 119.7(18) ?
C17 C22 H22 119.0(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C20 1.390(4)
O1 C1 1.450(4)
O2 C9 1.398(4)
O2 C8 1.447(4)
C1 C2 1.513(5)
C1 H1A 0.99(3)
C1 H1B 1.03(4)
C2 C3 1.401(5)
C2 C7 1.422(5)
C3 C4 1.382(6)
C3 H3 0.94(4)
C4 C5 1.400(6)
C4 H4 1.07(4)
C5 C6 1.397(5)
C5 H5 1.05(4)
C6 C7 1.392(5)
C6 H6 0.94(4)
C7 C8 1.508(5)
C8 H8A 1.02(4)
C8 H8B 0.99(4)
C9 C14 1.388(5)
C9 C10 1.391(5)
C10 C11 1.392(5)
C10 H10 1.02(4)
C11 C12 1.388(5)
C11 H11 0.98(3)
C12 C13 1.400(5)
C12 C15 1.502(5)
C13 C14 1.386(5)
C13 H13 1.07(4)
C14 H14 1.02(3)
C15 C16 1.328(5)
C15 H15 0.98(4)
C16 C17 1.493(5)
C16 H16 1.03(4)
C17 C18 1.387(5)
C17 C22 1.399(4)
C18 C19 1.393(5)
C18 H18 1.00(3)
C19 C20 1.384(5)
C19 H19 0.92(3)
C20 C21 1.387(5)
C21 C22 1.388(5)
C21 H21 0.95(3)
C22 H22 1.07(3)
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
_geom_hbond_publ_flag
C8 H8A O2 3_565 1.02(4) 2.41(4) 3.256(4) 140(3) yes
C1 H1B O1 3_665 1.03(4) 2.50(4) 3.497(4) 161(3) yes
C18 H18 CgC 2_655 1.00(3) 2.65(4) 3.385(4) 130(3) yes
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
C20 O1 C1 C2 77.7(4)
O1 C1 C2 C3 59.2(4)
O1 C1 C2 C7 -124.0(3)
C7 C2 C3 C4 -1.7(5)
C1 C2 C3 C4 175.3(3)
C2 C3 C4 C5 -0.1(6)
C3 C4 C5 C6 1.0(6)
C4 C5 C6 C7 -0.1(6)
C5 C6 C7 C2 -1.7(5)
C5 C6 C7 C8 179.9(3)
C3 C2 C7 C6 2.5(5)
C1 C2 C7 C6 -174.2(3)
C3 C2 C7 C8 -179.2(3)
C1 C2 C7 C8 4.0(5)
C9 O2 C8 C7 -87.6(4)
C6 C7 C8 O2 -38.4(4)
C2 C7 C8 O2 143.3(3)
C8 O2 C9 C14 79.5(4)
C8 O2 C9 C10 -100.2(4)
C14 C9 C10 C11 -5.7(5)
O2 C9 C10 C11 173.9(3)
C9 C10 C11 C12 -1.7(5)
C10 C11 C12 C13 7.9(5)
C10 C11 C12 C15 -161.4(3)
C11 C12 C13 C14 -7.0(5)
C15 C12 C13 C14 162.8(3)
C12 C13 C14 C9 -0.1(5)
C10 C9 C14 C13 6.6(5)
O2 C9 C14 C13 -173.0(3)
C11 C12 C15 C16 105.4(4)
C13 C12 C15 C16 -64.0(5)
C12 C15 C16 C17 -2.1(5)
C15 C16 C17 C18 113.3(4)
C15 C16 C17 C22 -60.1(5)
C22 C17 C18 C19 5.6(5)
C16 C17 C18 C19 -167.9(3)
C17 C18 C19 C20 -1.1(5)
C18 C19 C20 C21 -4.6(5)
C18 C19 C20 O1 -179.4(3)
C1 O1 C20 C19 -135.2(3)
C1 O1 C20 C21 50.1(4)
C19 C20 C21 C22 5.6(5)
O1 C20 C21 C22 -179.9(3)
C20 C21 C22 C17 -0.9(5)
C18 C17 C22 C21 -4.6(5)
C16 C17 C22 C21 169.2(3)