#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2002109.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_2002109
loop_
_publ_author_name
'Ferguson, G.'
'Kaitner, B.'
'McKervey, M. A.'
'Owens, M.'
_publ_section_title
;
 5-Chloro-2-hydroxycarbonylmethoxy-1,3-xylyl-18-crown-5 and
 5-chloro-2-ethoxycarbonylmethoxy-1,3-xylyl-18-crown-5
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              179
_journal_page_last               182
_journal_volume                  49
_journal_year                    1993
_chemical_formula_moiety         'C20 H29 Cl O8 '
_chemical_formula_sum            'C20 H29 Cl O8'
_chemical_formula_weight         432.89
_chemical_name_systematic
;
 5-chloro-2-ethoxycarbonylmethoxy-1,3-xylyl-18-crown-5
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   17.884(3)
_cell_length_b                   8.792(3)
_cell_length_c                   13.918(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      18.00
_cell_measurement_theta_min      10.00
_cell_volume                     2188.4(10)
_computing_cell_refinement       'Enraf-Nonius CAD-4 software'
_computing_data_collection       'Enraf-Nonius CAD-4 software'
_computing_data_reduction
'NRCVAX DATRD2 (Gabe, Le Page, Charland, Lee & White, 1989)'
_computing_molecular_graphics    'NRCVAX (Gabe et al., 1989)'
_computing_publication_material  'NRCVAX TABLES (Gabe et al., 1989)'
_computing_structure_refinement  'NRCVAX LSTSQ (Gabe et al., 1989)'
_computing_structure_solution    'NRCVAX SOLVER (Gabe et al., 1989)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Nonius CAD-4    '
_diffrn_measurement_method
;\q/2\q scans [\q-scan width (0.6 + 0.35tan\q)\%, \q-scan rate 3.3\%
min^-1^, background counts for 15 s on each side of every scan]
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'xray tube'
_diffrn_radiation_type           'Molybdenum K\a'
_diffrn_radiation_wavelength     0.70930
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2482
_diffrn_reflns_theta_max         26.90
_diffrn_reflns_theta_min         0.00
_diffrn_standards_decay_%        '< 1.0'
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.21
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.13
_refine_ls_abs_structure_Rogers  1.000000
_refine_ls_extinction_coef       6054(18)
_refine_ls_extinction_method     'Larson (1970)'
_refine_ls_goodness_of_fit_obs   1.07
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         816
_refine_ls_R_factor_all          0.189
_refine_ls_R_factor_obs          0.033
_refine_ls_shift/esd_max         0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      1/[\s^2^(F)+0.0008F^2^]
_refine_ls_wR_factor_all         0.084
_refine_ls_wR_factor_obs         0.040
_reflns_number_observed          816
_reflns_number_total             2482
_reflns_observed_criterion       'Inet > 3.0\s(Inet)'
_[local]_cod_data_source_file    br1013.cif
_[local]_cod_data_source_block   br1013_structure_2_of_2
_[local]_cod_chemical_formula_sum_orig 'C20 H29 Cl O8 '
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2002109
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,y,1/2+z
1/2+x,-y,z
-x,-y,1/2+z
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
_atom_site_aniso_type_symbol
Cl 0.117(2) 0.0916(19) 0.082(2) 0.036(3) -0.061(4) 0.030(4) Cl
C1 0.066(6) 0.041(5) 0.043(6) -0.016(10) -0.003(13) -0.006(10) C
C2 0.059(6) 0.034(5) 0.063(6) 0.023(10) 0.003(13) -0.013(10) C
C3 0.062(6) 0.050(6) 0.079(7) 0.016(10) 0.009(14) 0.007(12) C
C4 0.089(8) 0.034(5) 0.062(7) 0.025(11) -0.032(13) 0.010(10) C
C5 0.073(7) 0.047(6) 0.069(7) -0.011(10) 0.006(13) 0.000(11) C
C6 0.056(6) 0.048(5) 0.064(7) -0.006(9) -0.022(12) 0.002(12) C
C7 0.071(7) 0.062(6) 0.080(7) -0.032(10) 0.009(12) 0.005(13) C
O8 0.050(4) 0.057(4) 0.066(4) 0.012(6) -0.006(6) -0.014(8) O
C9 0.049(6) 0.080(8) 0.075(7) -0.015(10) -0.003(10) 0.023(13) C
C10 0.038(5) 0.103(9) 0.064(6) 0.014(11) 0.017(10) -0.017(13) C
O11 0.059(4) 0.059(4) 0.060(4) 0.022(6) 0.014(7) -0.009(7) O
C12 0.055(6) 0.068(7) 0.062(7) 0.028(10) -0.008(11) -0.022(12) C
C13 0.079(7) 0.056(6) 0.060(6) 0.034(10) -0.015(13) -0.002(12) C
O14 0.066(4) 0.073(4) 0.049(4) 0.010(7) 0.000(7) 0.014(8) O
C15 0.102(8) 0.052(6) 0.053(6) -0.018(12) 0.024(13) 0.003(11) C
C16 0.092(8) 0.054(7) 0.071(7) -0.033(11) 0.006(11) -0.027(12) C
O17 0.045(4) 0.070(4) 0.078(4) -0.014(6) -0.010(6) -0.013(8) O
C18 0.067(7) 0.073(7) 0.069(7) -0.037(10) -0.003(11) 0.012(12) C
C19 0.046(5) 0.086(7) 0.058(6) 0.016(9) 0.020(11) 0.022(12) C
O20 0.063(4) 0.069(4) 0.056(4) 0.003(7) 0.019(7) 0.016(7) O
C21 0.065(6) 0.062(7) 0.076(8) 0.018(10) 0.019(13) -0.013(12) C
O22 0.077(4) 0.044(4) 0.055(4) -0.009(6) -0.026(8) -0.008(7) O
C23 0.061(6) 0.038(5) 0.062(8) 0.014(9) -0.020(10) -0.004(10) C
C24 0.040(5) 0.055(6) 0.050(7) -0.008(10) -0.027(10) 0.008(10) C
O25 0.065(4) 0.077(4) 0.051(4) 0.022(7) 0.013(7) -0.032(8) O
O26 0.063(4) 0.071(4) 0.037(4) 0.020(7) -0.001(6) 0.011(7) O
C27 0.073(6) 0.092(8) 0.054(7) -0.004(12) -0.007(11) 0.043(13) C
C28 0.068(7) 0.211(13) 0.067(8) 0.051(15) 0.000(11) 0.100(18) C
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_type_symbol
Cl 0.32614(16) 0.0732(3) 0.00000 0.097(2) Uani ? Cl
C1 0.4416(5) -0.1099(9) 0.2619(8) 0.050(6) Uani ? C
C2 0.3638(5) -0.0940(9) 0.2628(8) 0.052(6) Uani ? C
C3 0.3291(4) -0.0387(9) 0.1817(9) 0.064(6) Uani ? C
C4 0.3705(6) 0.0004(9) 0.1011(8) 0.062(6) Uani ? C
C5 0.4469(6) -0.0186(9) 0.1002(8) 0.063(7) Uani ? C
C6 0.4838(4) -0.0714(9) 0.1821(8) 0.056(6) Uani ? C
C7 0.5665(5) -0.0938(10) 0.1809(8) 0.071(6) Uani ? C
O8 0.5804(3) -0.2510(6) 0.1660(5) 0.058(4) Uani ? O
C9 0.6557(5) -0.2950(11) 0.1815(7) 0.068(7) Uani ? C
C10 0.6602(4) -0.4654(12) 0.1788(8) 0.068(7) Uani ? C
O11 0.6209(3) -0.5234(6) 0.2592(5) 0.059(4) Uani ? O
C12 0.6149(4) -0.6844(11) 0.2611(8) 0.062(6) Uani ? C
C13 0.5715(5) -0.7340(10) 0.3462(7) 0.065(6) Uani ? C
O14 0.4939(3) -0.7035(6) 0.3343(5) 0.062(4) Uani ? O
C15 0.4519(6) -0.7625(10) 0.4113(7) 0.069(6) Uani ? C
C16 0.3704(6) -0.7273(11) 0.3969(7) 0.072(7) Uani ? C
O17 0.3591(3) -0.5727(7) 0.4196(5) 0.064(4) Uani ? O
C18 0.2835(5) -0.5325(10) 0.4165(8) 0.070(6) Uani ? C
C19 0.2776(4) -0.3644(10) 0.4261(7) 0.063(6) Uani ? C
O20 0.3066(3) -0.2953(7) 0.3418(5) 0.063(4) Uani ? O
C21 0.3193(5) -0.1362(10) 0.3492(8) 0.068(6) Uani ? C
O22 0.4779(3) -0.1481(6) 0.3461(5) 0.059(4) Uani ? O
C23 0.4895(4) -0.3067(9) 0.3662(7) 0.054(6) Uani ? C
C24 0.4893(5) -0.3212(10) 0.4752(7) 0.048(5) Uani ? C
O25 0.4486(3) -0.2531(7) 0.5267(5) 0.064(4) Uani ? O
O26 0.5403(3) -0.4222(6) 0.5019(4) 0.057(4) Uani ? O
C27 0.5472(5) -0.4479(11) 0.6047(8) 0.073(7) Uani ? C
C28 0.6181(6) -0.5116(16) 0.6270(8) 0.116(9) Uani ? C
H3 0.276 -0.027 0.181 0.0733 Uiso calc H
H5 0.475 0.004 0.044 0.0731 Uiso calc H
H7A 0.587 -0.062 0.241 0.0807 Uiso calc H
H7B 0.588 -0.036 0.130 0.0807 Uiso calc H
H9A 0.686 -0.253 0.132 0.0779 Uiso calc H
H9B 0.672 -0.259 0.242 0.0779 Uiso calc H
H10A 0.711 -0.497 0.182 0.0781 Uiso calc H
H10B 0.638 -0.502 0.121 0.0781 Uiso calc H
H12A 0.590 -0.718 0.205 0.0716 Uiso calc H
H12B 0.664 -0.727 0.264 0.0716 Uiso calc H
H13A 0.589 -0.681 0.401 0.0749 Uiso calc H
H13B 0.578 -0.840 0.355 0.0749 Uiso calc H
H15A 0.459 -0.870 0.414 0.0790 Uiso calc H
H15B 0.469 -0.718 0.470 0.0790 Uiso calc H
H16A 0.341 -0.789 0.438 0.0823 Uiso calc H
H16B 0.357 -0.745 0.332 0.0823 Uiso calc H
H18A 0.262 -0.564 0.357 0.0796 Uiso calc H
H18B 0.257 -0.580 0.468 0.0796 Uiso calc H
H19A 0.306 -0.332 0.480 0.0734 Uiso calc H
H19B 0.227 -0.336 0.434 0.0734 Uiso calc H
H21A 0.273 -0.083 0.350 0.0776 Uiso calc H
H21B 0.346 -0.114 0.406 0.0776 Uiso calc H
H23A 0.450 -0.366 0.339 0.0637 Uiso calc H
H23B 0.536 -0.339 0.341 0.0637 Uiso calc H
H27A 0.509 -0.516 0.625 0.0831 Uiso calc H
H27B 0.542 -0.354 0.637 0.0831 Uiso calc H
H28C 0.622 -0.528 0.694 0.1257 Uiso calc H
H28A 0.624 -0.606 0.595 0.1257 Uiso calc H
H28B 0.657 -0.444 0.607 0.1257 Uiso calc H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002 'International Tables Vol. IV Table 2.2B'
H 0.000 0.000 'International Tables Vol. IV Table 2.2B'
Cl 0.132 0.159 'International Tables Vol. IV Table 2.2B'
O 0.008 0.006 'International Tables Vol. IV Table 2.2B'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 2 1
2 2 -1
2 -2 1
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
C(2) C(1) C(6) 121.7(10) no
C(2) C(1) O(22) 119.0(9) no
C(6) C(1) O(22) 118.9(8) no
C(1) C(2) C(3) 118.4(10) no
C(1) C(2) C(21) 120.9(10) no
C(3) C(2) C(21) 120.6(8) no
C(2) C(3) C(4) 120.7(8) no
Cl C(4) C(3) 120.2(8) no
Cl C(4) C(5) 119.4(9) no
C(3) C(4) C(5) 120.4(9) no
C(4) C(5) C(6) 120.1(9) no
C(1) C(6) C(5) 118.6(8) no
C(1) C(6) C(7) 121.1(9) no
C(5) C(6) C(7) 120.2(10) no
C(6) C(7) O(8) 107.7(7) no
C(7) O(8) C(9) 114.3(6) no
O(8) C(9) C(10) 108.7(6) no
C(9) C(10) O(11) 108.2(7) no
C(10) O(11) C(12) 114.3(7) no
O(11) C(12) C(13) 110.4(7) no
C(12) C(13) O(14) 111.3(8) no
C(13) O(14) C(15) 111.2(7) no
O(14) C(15) C(16) 109.9(8) no
C(15) C(16) O(17) 107.9(7) no
C(16) O(17) C(18) 112.0(6) no
O(17) C(18) C(19) 108.4(6) no
C(18) C(19) O(20) 109.0(8) no
C(19) O(20) C(21) 114.9(7) no
C(2) C(21) O(20) 105.9(7) no
C(1) O(22) C(23) 117.9(6) no
O(22) C(23) C(24) 106.0(7) no
C(23) C(24) O(25) 124.3(8) no
C(23) C(24) O(26) 109.4(8) no
O(25) C(24) O(26) 126.2(9) no
C(24) O(26) C(27) 116.0(7) no
O(26) C(27) C(28) 110.6(8) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C(4) 1.737(10) no
C(1) C(2) 1.398(12) no
C(1) C(6) 1.385(15) no
C(1) O(22) 1.381(13) no
C(2) C(3) 1.377(16) no
C(2) C(21) 1.488(15) no
C(3) C(4) 1.387(16) no
C(4) C(5) 1.377(15) no
C(5) C(6) 1.397(15) no
C(6) C(7) 1.492(12) no
C(7) O(8) 1.420(10) no
O(8) C(9) 1.416(10) no
C(9) C(10) 1.501(14) no
C(10) O(11) 1.416(12) no
O(11) C(12) 1.420(11) no
C(12) C(13) 1.481(15) no
C(13) O(14) 1.423(10) no
O(14) C(15) 1.406(12) no
C(15) C(16) 1.504(15) no
C(16) O(17) 1.410(12) no
O(17) C(18) 1.399(11) no
C(18) C(19) 1.488(13) no
C(19) O(20) 1.418(12) no
O(20) C(21) 1.421(11) no
O(22) C(23) 1.437(10) no
C(23) C(24) 1.522(14) no
C(24) O(25) 1.184(12) no
C(24) O(26) 1.327(11) no
O(26) C(27) 1.454(12) no
C(27) C(28) 1.421(14) no
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
_geom_torsion_publ_flag
C6 C1 C2 C3 0.1(5) no
C6 C1 C2 C21 179.9(12) no
O22 C1 C2 C3 172.5(12) no
O22 C1 C2 C21 -7.8(5) no
C2 C1 C6 C5 -1.4(6) no
C2 C1 C6 C7 -178.0(12) no
O22 C1 C6 C5 -173.8(12) no
O22 C1 C6 C7 9.6(5) no
C2 C1 O22 C23 90.8(8) no
C6 C1 O22 C23 -96.6(8) no
C1 C2 C3 C4 -0.1(6) no
C21 C2 C3 C4 -179.9(12) no
C1 C2 C21 O20 -84.4(9) no
C3 C2 C21 O20 95.3(9) no
C2 C3 C4 CL -178.8(11) no
C2 C3 C4 C5 1.5(6) no
CL C4 C5 C6 177.5(11) no
C3 C4 C5 C6 -2.8(5) no
C4 C5 C6 C1 2.7(6) no
C4 C5 C6 C7 179.3(12) no
C1 C6 C7 O8 77.1(8) no
C5 C6 C7 O8 -99.4(9) no
C6 C7 O8 C9 -168.5(10) no
C7 O8 C9 C10 171.1(10) no
O8 C9 C10 O11 -66.8(7) no
C9 C10 O11 C12 174.7(10) no
C10 O11 C12 C13 -178.7(10) no
O11 C12 C13 O14 73.8(7) no
C12 C13 O14 C15 174.8(10) no
C13 O14 C15 C16 179.6(11) no
O14 C15 C16 O17 -76.2(8) no
C15 C16 O17 C18 -174.8(11) no
C16 O17 C18 C19 -171.3(10) no
O17 C18 C19 O20 69.0(7) no
C18 C19 O20 C21 -167.2(10) no
C19 O20 C21 C2 168.3(10) no
C1 O22 C23 C24 -149.9(9) no
O22 C23 C24 O25 39.2(5) no
O22 C23 C24 O26 -141.7(10) no
C23 C24 O26 C27 179.6(10) no
O25 C24 O26 C27 -1.3(5) no
C24 O26 C27 C28 -159.0(11) no