#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2002108.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_2002108
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         'C18 H25 Cl O8 '
_chemical_formula_sum            'C18 H25 Cl O8'
_chemical_formula_weight         404.84
_chemical_name_systematic
;
5-chloro-2-hydroxycarbonylmethoxy-1,3-xylyl-18-crown-5
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   13.856(2)
_cell_length_b                   18.783(4)
_cell_length_c                   15.209(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      15.00
_cell_measurement_theta_min      10.00
_cell_volume                     3958.3(11)
_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       'Enraf-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       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4301
_diffrn_reflns_theta_max         26.92
_diffrn_reflns_theta_min         0.00
_diffrn_standards_decay_%        '< 1.0'
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.23
_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    1.359
_exptl_crystal_description       needle
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.21
_refine_ls_extinction_coef       473E1(2)
_refine_ls_extinction_method     'Larson (1970)'
_refine_ls_goodness_of_fit_obs   1.24
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         1930
_refine_ls_R_factor_all          0.112
_refine_ls_R_factor_obs          0.036
_refine_ls_shift/esd_max         0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      1/[\s^2^(F)+0.0008F^2^]
_refine_ls_wR_factor_all         0.059
_refine_ls_wR_factor_obs         0.048
_reflns_number_observed          1930
_reflns_number_total             4301
_reflns_observed_criterion       'Inet > 3.0\s(Inet)'
_[local]_cod_data_source_file    br1013.cif
_[local]_cod_data_source_block   br1013_structure_1_of_2
_[local]_cod_chemical_formula_sum_orig 'C18 H25 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               2002108
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
1/2-x,1/2+y,z
1/2+x,1/2-y,-z
x,1/2-y,1/2+z
-x,1/2+y,1/2-z
1/2-x,-y,1/2+z
1/2+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 0.1027(7) 0.0641(5) 0.0723(6) -0.0007(10) 0.0403(10) -0.0476(8) Cl
C1 0.0434(15) 0.0478(16) 0.0435(14) 0.008(3) -0.022(3) -0.004(3) C
C2 0.0427(15) 0.0471(16) 0.0421(16) -0.009(3) -0.017(3) -0.004(3) C
C3 0.0615(19) 0.0423(15) 0.0449(16) -0.011(3) -0.019(3) -0.005(3) C
C4 0.0611(19) 0.0497(17) 0.0413(16) 0.003(3) -0.007(3) -0.016(3) C
C5 0.0563(18) 0.0604(19) 0.0395(15) -0.011(3) -0.001(3) 0.002(3) C
C6 0.0494(17) 0.0468(16) 0.0434(15) -0.006(3) -0.024(3) 0.010(3) C
C7 0.064(2) 0.0528(17) 0.0577(19) -0.011(3) -0.023(3) 0.021(3) C
O8 0.0509(11) 0.0430(10) 0.0612(11) 0.0025(18) -0.007(2) 0.0046(18) O
C9 0.0480(17) 0.0544(17) 0.0593(18) 0.001(3) 0.013(3) 0.002(3) C
C10 0.0469(17) 0.0564(18) 0.069(2) -0.012(3) 0.005(3) 0.002(3) C
O11 0.0505(11) 0.0552(12) 0.0520(11) -0.0199(19) 0.0005(19) -0.0033(19) O
C12 0.0533(18) 0.0621(19) 0.0611(19) -0.008(3) -0.012(3) -0.022(3) C
C13 0.061(2) 0.0600(19) 0.0573(19) 0.013(3) -0.020(3) -0.011(3) C
O14 0.0574(12) 0.0511(11) 0.0517(12) -0.0017(19) -0.002(2) -0.0004(19) O
C15 0.083(2) 0.064(2) 0.0489(17) -0.017(4) 0.011(4) -0.018(3) C
C16 0.090(3) 0.071(2) 0.0483(18) -0.032(4) 0.000(4) 0.016(3) C
O17 0.0783(15) 0.0519(12) 0.0556(12) -0.016(2) 0.000(2) -0.011(2) O
C18 0.082(2) 0.0563(19) 0.0481(17) -0.020(3) 0.034(3) 0.002(3) C
C19 0.069(2) 0.0549(18) 0.0613(19) -0.025(3) 0.049(4) -0.008(3) C
O20 0.0501(11) 0.0592(12) 0.0455(11) -0.0191(19) 0.0145(19) -0.0029(18) O
C21 0.0502(17) 0.0564(18) 0.0567(19) -0.019(3) -0.004(3) -0.006(3) C
O22 0.0447(11) 0.0552(12) 0.0656(12) 0.0205(18) -0.021(2) -0.027(2) O
C23 0.0460(16) 0.0447(16) 0.0521(16) 0.008(3) 0.004(3) -0.007(3) C
C24 0.0361(15) 0.0477(16) 0.0626(19) 0.003(3) 0.003(3) -0.004(3) C
O25 0.0665(14) 0.0543(13) 0.0874(16) 0.027(2) -0.045(2) 0.010(2) O
O26 0.0618(13) 0.0442(12) 0.0733(14) 0.015(2) -0.021(3) -0.010(2) O
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 0.50333(7) 0.89173(4) 0.60044(6) 0.0797(5) Uani ? Cl
C1 0.35520(19) 1.06334(14) 0.75566(17) 0.0449(14) Uani ? C
C2 0.33193(19) 0.99214(14) 0.77150(17) 0.0440(14) Uani ? C
C3 0.3768(2) 0.94001(14) 0.72211(17) 0.0496(16) Uani ? C
C4 0.4439(2) 0.95809(15) 0.65933(17) 0.0507(16) Uani ? C
C5 0.4668(2) 1.02842(15) 0.64367(18) 0.0521(16) Uani ? C
C6 0.4221(2) 1.08182(14) 0.69149(18) 0.0465(15) Uani ? C
C7 0.4461(2) 1.15886(16) 0.67325(19) 0.0582(17) Uani ? C
O8 0.49328(14) 1.19327(9) 0.74421(14) 0.0517(11) Uani ? O
C9 0.5876(2) 1.16658(15) 0.76058(19) 0.0539(17) Uani ? C
C10 0.6274(2) 1.20324(15) 0.8395(2) 0.0574(18) Uani ? C
O11 0.57928(13) 1.17780(9) 0.91546(12) 0.0526(11) Uani ? O
C12 0.6084(2) 1.21292(16) 0.9936(2) 0.0588(17) Uani ? C
C13 0.5644(2) 1.17673(15) 1.07095(19) 0.0593(18) Uani ? C
O14 0.46227(14) 1.18589(9) 1.06965(12) 0.0534(11) Uani ? O
C15 0.4145(2) 1.15934(17) 1.14635(19) 0.0653(19) Uani ? C
C16 0.4016(3) 1.08075(17) 1.1466(2) 0.070(2) Uani ? C
O17 0.33303(15) 1.06211(10) 1.08145(12) 0.0619(12) Uani ? O
C18 0.3186(2) 0.98798(15) 1.0771(2) 0.0623(19) Uani ? C
C19 0.2579(2) 0.97177(16) 1.00013(19) 0.0618(18) Uani ? C
O20 0.31356(13) 0.98347(9) 0.92366(12) 0.0516(10) Uani ? O
C21 0.2630(2) 0.97313(15) 0.84338(19) 0.0545(17) Uani ? C
O22 0.30339(13) 1.11582(9) 0.79835(13) 0.0552(11) Uani ? O
C23 0.34527(19) 1.14527(14) 0.87641(18) 0.0476(15) Uani ? C
C24 0.3259(2) 1.22368(15) 0.8785(2) 0.0488(16) Uani ? C
O25 0.28043(15) 1.25648(10) 0.82499(15) 0.0694(13) Uani ? O
O26 0.36141(15) 1.25680(11) 0.94949(16) 0.0598(13) Uani ? O
H(O26) 0.393(2) 1.2280(17) 0.981(2) 0.088(13) Uiso ? H
H3 0.361 0.891 0.732 0.0596 Uiso calc H
H5 0.513 1.040 0.600 0.0620 Uiso calc H
H7A 0.388 1.184 0.661 0.0682 Uiso calc H
H7B 0.487 1.161 0.623 0.0682 Uiso calc H
H9A 0.585 1.117 0.771 0.0639 Uiso calc H
H9B 0.628 1.176 0.711 0.0639 Uiso calc H
H10A 0.618 1.253 0.834 0.0674 Uiso calc H
H10B 0.694 1.194 0.844 0.0674 Uiso calc H
H12A 0.677 1.211 0.998 0.0688 Uiso calc H
H12B 0.588 1.261 0.992 0.0688 Uiso calc H
H13A 0.590 1.197 1.123 0.0693 Uiso calc H
H13B 0.579 1.127 1.069 0.0693 Uiso calc H
H15A 0.452 1.172 1.196 0.0753 Uiso calc H
H15B 0.353 1.181 1.150 0.0753 Uiso calc H
H16A 0.379 1.066 1.203 0.0796 Uiso calc H
H16B 0.461 1.058 1.134 0.0796 Uiso calc H
H18A 0.379 0.965 1.071 0.0723 Uiso calc H
H18B 0.287 0.972 1.129 0.0723 Uiso calc H
H19A 0.203 1.002 1.000 0.0718 Uiso calc H
H19B 0.238 0.924 1.002 0.0718 Uiso calc H
H21A 0.243 0.925 0.838 0.0645 Uiso calc H
H21B 0.208 1.003 0.841 0.0645 Uiso calc H
H23A 0.317 1.123 0.927 0.0576 Uiso calc H
H23B 0.413 1.137 0.876 0.0576 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
0 12 3
8 1 1
1 9 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) 120.9(3) no
C(2) C(1) O(22) 118.8(2) no
C(6) C(1) O(22) 119.9(2) no
C(1) C(2) C(3) 118.8(3) no
C(1) C(2) C(21) 120.2(2) no
C(3) C(2) C(21) 121.1(2) no
C(2) C(3) C(4) 120.4(2) no
Cl C(4) C(3) 120.0(2) no
Cl C(4) C(5) 119.2(2) no
C(3) C(4) C(5) 120.8(3) no
C(4) C(5) C(6) 120.0(3) no
C(1) C(6) C(5) 119.1(2) no
C(1) C(6) C(7) 121.0(3) no
C(5) C(6) C(7) 120.0(3) no
C(6) C(7) O(8) 113.5(2) no
C(7) O(8) C(9) 113.4(2) no
O(8) C(9) C(10) 108.6(2) no
C(9) C(10) O(11) 109.1(2) no
C(10) O(11) C(12) 113.1(2) no
O(11) C(12) C(13) 109.4(2) no
C(12) C(13) O(14) 109.9(2) no
C(13) O(14) C(15) 113.9(2) no
O(14) C(15) C(16) 113.8(2) no
C(15) C(16) O(17) 108.9(3) no
C(16) O(17) C(18) 111.9(2) no
O(17) C(18) C(19) 108.8(3) no
C(18) C(19) O(20) 108.1(3) no
C(19) O(20) C(21) 114.6(2) no
C(2) C(21) O(20) 106.3(2) no
C(1) O(22) C(23) 117.03(19) no
O(22) C(23) C(24) 108.9(2) no
C(23) C(24) O(25) 125.8(3) no
C(23) C(24) O(26) 114.1(3) no
O(25) C(24) O(26) 120.1(3) no
C(24) O(26) H(O26) 111.(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C(4) 1.742(3) no
C(1) C(2) 1.397(4) no
C(1) C(6) 1.390(4) no
C(1) O(22) 1.381(3) no
C(2) C(3) 1.382(4) no
C(2) C(21) 1.495(4) no
C(3) C(4) 1.376(4) no
C(4) C(5) 1.379(4) no
C(5) C(6) 1.385(4) no
C(6) C(7) 1.510(4) no
C(7) O(8) 1.418(4) no
O(8) C(9) 1.421(3) no
C(9) C(10) 1.489(4) no
C(10) O(11) 1.417(3) no
O(11) C(12) 1.418(3) no
C(12) C(13) 1.490(4) no
C(13) O(14) 1.425(4) no
O(14) C(15) 1.431(4) no
C(15) C(16) 1.487(5) no
C(16) O(17) 1.416(4) no
O(17) C(18) 1.408(3) no
C(18) C(19) 1.474(5) no
C(19) O(20) 1.413(3) no
O(20) C(21) 1.421(3) no
O(22) C(23) 1.433(3) no
C(23) C(24) 1.497(4) no
C(24) O(25) 1.199(4) no
C(24) O(26) 1.340(4) no
O(26) H(O26) 0.85(3) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
O(26) O(14) 2.658(3) no
H(O26) O(14) 1.83(3) 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 0.0(2) no
C6 C1 C2 C21 177.4(3) no
O22 C1 C2 C3 173.4(3) no
O22 C1 C2 C21 -9.30(10) no
C2 C1 C6 C5 -0.7(2) no
C2 C1 C6 C7 178.9(3) no
O22 C1 C6 C5 -174.0(3) no
O22 C1 C6 C7 5.70(10) no
C2 C1 O22 C23 97.4(2) no
C6 C1 O22 C23 -89.2(2) no
C1 C2 C3 C4 0.8(2) no
C21 C2 C3 C4 -176.5(3) no
C1 C2 C21 O20 -73.4(2) no
C3 C2 C21 O20 103.9(3) no
C2 C3 C4 CL 177.6(3) no
C2 C3 C4 C5 -0.9(2) no
CL C4 C5 C6 -178.3(3) no
C3 C4 C5 C6 0.2(2) no
C4 C5 C6 C1 0.6(2) no
C4 C5 C6 C7 -179.0(3) no
C1 C6 C7 O8 66.2(2) no
C5 C6 C7 O8 -114.1(3) no
C6 C7 O8 C9 67.2(2) no
C7 O8 C9 C10 -176.5(3) no
O8 C9 C10 O11 72.1(2) no
C9 C10 O11 C12 -176.4(3) no
C10 O11 C12 C13 -172.6(3) no
O11 C12 C13 O14 -66.6(2) no
C12 C13 O14 C15 -173.8(3) no
C13 O14 C15 C16 -78.7(3) no
O14 C15 C16 O17 -69.4(2) no
C15 C16 O17 C18 179.0(4) no
C16 O17 C18 C19 -171.8(3) no
O17 C18 C19 O20 71.0(2) no
C18 C19 O20 C21 -177.2(3) no
C19 O20 C21 C2 176.7(3) no
C1 O22 C23 C24 141.3(3) no
O22 C23 C24 O25 2.00(10) no
O22 C23 C24 O26 179.5(3) no