#------------------------------------------------------------------------------
#$Date: 2017-10-20 20:12:10 +0300 (Fri, 20 Oct 2017) $
#$Revision: 202206 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/17/2001745.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_2001745
loop_
_publ_author_name
'Clark, G. R.'
_publ_section_title
;
 Structure of a bromine derivative of isostegane
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1028
_journal_page_last               1031
_journal_paper_doi               10.1107/S0108270192012654
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C22.5 H24 Br Cl O6'
_chemical_formula_weight         505.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_type_scat_source           'SHELX76 (Sheldrick, 1976)'
_cell_angle_alpha                90.0
_cell_angle_beta                 102.120(10)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   9.0280(10)
_cell_length_b                   11.069(2)
_cell_length_c                   23.465(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      14.75
_cell_measurement_theta_min      13.11
_cell_volume                     2292.6(5)
_diffrn_measurement_device       'Nonius CAD-4'
_diffrn_measurement_method       2θ/ω
_diffrn_radiation_type           Mo
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4359
_diffrn_reflns_theta_max         25
_diffrn_standards_decay_%        -5
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.05
_exptl_absorpt_correction_T_max  0.9990
_exptl_absorpt_correction_T_min  0.9045
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      1.470(10)
_exptl_crystal_density_method    'flotation in aq. KCl/KI'
_exptl_crystal_description       Needle
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.41
_refine_ls_goodness_of_fit_obs   3.06
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2048
_refine_ls_R_factor_obs          0.063
_refine_ls_shift/esd_max         -0.117
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 2.2868/(σ²F+0.001001F²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.067
_reflns_number_observed          2048
_reflns_number_total             3526
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            hu1024.cif
_cod_data_source_block           hu1024_structure_1_of_1
_cod_depositor_comments
;
 Updating space group information and adding the symmetry operation list.

 Antanas Vaitkus,
 2017-10-20

 Correcting the _geom_angle_atom_site_label_* data item values by changing
 them from 'C(3AA)', 'C(40B)', 'O(7A)', 'C1(2S)' and 'C1(1S)' to
 'C(3aA)', 'C(4aB)', 'O(7'B)', 'Cl(2S)' and 'Cl(1S)' respectively.

 Antanas Vaitkus,
 2017-10-20

 Marking attached hydrogen atoms.

 Antanas Vaitkus,
 2017-10-20

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '2.2868/(\s^2^F+0.001001F^2^)'
was changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
2.2868/(\s^2^F+0.001001F^2^)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2292
_cod_original_sg_symbol_Hall     'P 2y1'
_cod_database_code               2001745
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_attached_hydrogens
Br(A) .1746(2) .00000 .22358(8) ? 0
O(1'A) -.3034(15) -.2963(14) -.0813(6) .082(4) 0
C(1A) -.2660(19) -.3246(16) -.0303(7) .049(5) 0
O(2A) -.3031(13) -.4404(12) -.0117(5) .065(4) 0
C(3A) -.2344(19) -.4554(16) .0486(8) .052(5) 2
C(3aA) -.0989(17) -.3665(18) .0550(7) .046(4) 1
C(4A) -.0246(18) -.3386(17) .1208(7) .051(5) 2
C(4aA) .1333(18) -.2927(15) .1211(7) .043(4) 0
C(5A) .2500(18) -.3803(16) .1303(7) .048(4) 1
O(6'A) .5184(14) -.4243(13) .1362(6) .070(4) 0
C(6A) .3959(17) -.3440(15) .1307(6) .040(4) 0
C(6'A) .478(2) -.559(2) .1395(11) .083(7) 3
O(7'A) .5881(13) -.1968(12) .1314(5) .063(4) 0
C(7A) .4332(19) -.2236(17) .1277(7) .048(5) 0
C(7'A) .632(2) -.071(2) .1447(10) .083(7) 3
C(8A) .3178(19) -.1373(16) .1219(7) .049(5) 1
C(8aA) .1682(17) -.1704(14) .1172(6) .035(4) 0
C(8bA) .0532(17) -.0757(15) .1060(6) .037(4) 0
C(9A) .0497(17) .0171(16) .1468(7) .045(4) 0
O(10'A) -.0529(13) .1975(11) .1815(5) .062(3) 0
C(10A) -.0458(17) .1136(15) .1376(7) .040(4) 0
C(10'A) .029(3) .302(3) .1833(11) .102(8) 3
O(11'A) -.2361(12) .2242(11) .0759(5) .053(3) 0
C(11A) -.1450(18) .1249(17) .0839(7) .049(4) 0
C(11'A) -.351(2) .2255(18) .0249(8) .063(5) 3
C(12A) -.1460(17) .0341(14) .0428(6) .036(4) 1
C(12aA) -.0497(15) -.0632(14) .0534(6) .031(4) 0
C(13A) -.0642(17) -.1619(15) .0080(7) .045(4) 2
C(13aA) -.1775(18) -.2632(17) .0205(7) .047(5) 1
Br(B) .0185(2) .1437(2) .34281(7) ? 0
O(1'B) .5625(15) .4495(13) .6331(6) .077(4) 0
C(1B) .451(2) .485(2) .5986(8) .066(5) 0
O(2B) .3865(14) .5936(12) .5984(5) .067(4) 0
C(3B) .267(2) .6101(17) .5504(8) .060(5) 2
C(3aB) .3089(19) .5176(17) .5050(7) .050(5) 1
C(4B) .1698(17) .4864(17) .4539(7) .048(4) 2
C(4aB) .2314(17) .4411(15) .4035(7) .041(4) 0
C(5B) .2583(18) .5301(15) .3619(7) .046(4) 1
O(6'B) .3650(14) .5755(13) .2759(6) .066(4) 0
C(6B) .3279(16) .4956(16) .3173(6) .039(4) 0
C(6'B) .303(2) .6990(19) .2776(9) .064(6) 3
O(7'B) .4442(15) .3533(13) .2673(6) .071(4) 0
C(7B) .3739(18) .3757(16) .3133(7) .042(4) 0
C(7'B) .507(2) .238(2) .2617(9) .079(6) 3
C(8B) .3501(18) .2933(15) .3504(7) .044(4) 1
C(8aB) .2807(18) .3243(15) .3982(7) .045(4) 0
C(8bB) .2564(16) .2230(14) .4377(6) .034(4) 0
C(9B) .1513(17) .1350(18) .4164(6) .041(4) 0
O(10'B) .0280(12) -.0557(11) .4306(5) .052(3) 0
C(10B) .1337(17) .0340(14) .4515(7) .041(4) 0
C(10'B) .099(2) -.154(2) .4025(9) .076(6) 3
O(11'B) .1931(12) -.0765(11) .5383(5) .053(3) 0
C(11B) .2132(17) .0250(14) .5066(7) .042(4) 0
C(11'B) .257(2) -.0760(18) .5997(8) .065(5) 3
C(12B) .3240(18) .1152(16) .5313(7) .048(5) 1
C(12aB) .3423(17) .2151(15) .4943(7) .040(4) 0
C(13B) .4472(17) .3105(15) .5220(7) .045(4) 2
C(13aB) .3589(18) .4136(16) .5473(7) .047(5) 1
C(S) .2862 .1290 .7394 .116 2
Cl(1S) .1172 .0620 .7268 ? 0
Cl(2S) .2834 .2578 .6968 ? 0
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
O(2A) C(1A) O(1'A) 120.1(16) yes
C(13aA) C(1A) O(1'A) 132.7(18) yes
C(13aA) C(1A) O(2A) 107.1(14) yes
C(3A) O(2A) C(1A) 109.2(13) yes
C(3aA) C(3A) O(2A) 101.0(13) yes
C(4A) C(3aA) C(3A) 112.5(14) yes
C(13aA) C(3aA) C(3A) 99.1(12) yes
C(13aA) C(3aA) C(4A) 115.9(16) yes
C(4aA) C(4A) C(3aA) 106.1(13) yes
C(5A) C(4aA) C(4A) 116.2(15) yes
C(8aA) C(4aA) C(4A) 123.4(15) yes
C(8aA) C(4aA) C(5A) 120.2(15) yes
C(6A) C(5A) C(4aA) 118.9(15) yes
C(6'A) O(6'A) C(6A) 115.2(15) yes
O(6'A) C(6A) C(5A) 123.4(15) yes
C(7A) C(6A) C(5A) 121.7(15) yes
C(7A) C(6A) O(6'A) 114.8(15) yes
C(7'A) O(7'A) C(7A) 115.9(14) yes
O(7'A) C(7A) C(6A) 116.6(15) yes
C(8A) C(7A) C(6A) 118.7(16) yes
C(8A) C(7A) O(7'A) 124.7(16) yes
C(8aA) C(8A) C(7A) 121.5(16) yes
C(8A) C(8aA) C(4aA) 118.8(15) yes
C(8bA) C(8aA) C(4aA) 123.1(15) yes
C(8bA) C(8aA) C(8A) 118.0(15) yes
C(9A) C(8bA) C(8aA) 121.2(13) yes
C(12aA) C(8bA) C(8aA) 123.4(14) yes
C(12aA) C(8bA) C(9A) 115.2(14) yes
C(8bA) C(9A) Br(A) 118.2(12) yes
C(10A) C(9A) Br(A) 117.0(12) yes
C(10A) C(9A) C(8bA) 124.6(14) yes
O(2B) C(1B) O(1'A) 126.6(19) yes
C(13aB) C(1B) O(1'B) 126.(2) yes
C(13aB) C(1B) O(2B) 107.4(15) yes
C(3B) O(2B) C(1B) 112.5(15) yes
C(3aB) C(3B) O(2B) 102.0(14) yes
C(4B) C(3aB) C(3B) 113.0(14) yes
C(13aB) C(3aB) C(3B) 97.5(13) yes
C(13aB) C(3aA) C(4B) 114.1(14) yes
C(4aB) C(4B) C(3aB) 107.7(12) yes
C(5B) C(4aB) C(4B) 116.7(14) yes
C(8aB) C(4aB) C(4B) 124.5(15) yes
C(8aB) C(4aB) C(5B) 118.3(15) yes
C(6B) C(5B) C(4aB) 119.4(15) yes
C(6'B) O(6'B) C(6B) 114.5(14) yes
O(6'B) C(6B) C(5B) 124.2(16) yes
C(7B) C(6B) C(5A) 120.1(16) yes
C(7B) C(6A) O(6'B) 115.6(14) yes
C(7'B) O(7'B) C(7B) 119.4(16) yes
O(7'B) C(7B) C(6B) 114.4(15) yes
C(8B) C(7B) C(6B) 121.6(16) yes
C(8B) C(7B) O(7'B) 124.0(16) yes
C(8aB) C(8A) C(7B) 120.8(16) yes
C(8A) C(8aA) C(4aB) 119.7(15) yes
C(8bA) C(8aB) C(4aB) 123.5(14) yes
C(8bA) C(8aB) C(8B) 116.6(14) yes
C(9B) C(8bB) C(8aA) 118.9(13) yes
C(12aB) C(8bB) C(8aB) 120.7(14) yes
C(12aB) C(8bB) C(9A) 120.3(14) yes
C(8bB) C(9B) Br(B) 123.5(13) yes
C(10B) C(9B) Br(B) 116.4(12) yes
C(10B) C(9B) C(8bB) 120.0(13) yes
C(10'A) O(10'A) C(10A) 118.3(16) yes
O(10'A) C(10A) C(9A) 121.9(13) yes
C(11A) C(10A) C(9A) 118.8(15) yes
C(11A) C(10A) O(10'A) 119.2(14) yes
C(11'A) O(11'A) C(11A) 116.1(14) yes
O(11'A) C(11A) C(10A) 117.0(15) yes
C(12A) C(11A) C(10A) 118.1(15) yes
C(12A) C(11A) O(11'A) 124.9(14) yes
C(12aA) C(12A) C(11A) 122.0(14) yes
C(12A) C(12aA) C(8bA) 121.3(14) yes
C(13A) C(12aA) C(8bA) 119.8(14) yes
C(13A) C(12aA) C(12A) 118.8(12) yes
C(13aA) C(13A) C(12aA) 110.1(13) yes
C(3aA) C(13aA) C(1A) 101.7(15) yes
C(13A) C(13aA) C(1A) 116.3(14) yes
C(13A) C(13aA) C(3aA) 113.0(13) yes
Cl(2S) C(S) Cl(1S) 111.1 yes
C(10'B) O(10'B) C(10B) 110.4(12) yes
O(10'B) C(10B) C(9B) 120.6(13) yes
C(11B) C(10B) C(9B) 121.0(14) yes
C(11B) C(10B) O(10'B) 118.3(14) yes
C(11'B) O(11'B) C(11B) 117.8(13) yes
O(11'B) C(11B) C(10B) 118.3(14) yes
C(12B) C(11B) C(10B) 121.3(15) yes
C(12B) C(11B) O(11'B) 120.3(13) yes
C(12aB) C(12B) C(11B) 116.5(14) yes
C(12B) C(12aB) C(8bB) 120.9(15) yes
C(13B) C(12aB) C(8bB) 123.6(15) yes
C(13B) C(12aB) C(12B) 115.4(13) yes
C(13aB) C(13B) C(12aB) 110.8(12) yes
C(13aB) C(13aB) C(1B) 99.0(15) yes
C(13B) C(13aB) C(1B) 116.0(14) yes
C(13B) C(13aA) C(3aB) 113.8(14) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C(9A) Br(A) 1.924(15) yes
C(1A) O(1'A) 1.21(2) yes
O(2A) C(1A) 1.42(2) yes
C(13aA) C(1A) 1.46(2) yes
C(3A) O(2A) 1.43(2) yes
C(3aA) C(3A) 1.55(2) yes
C(4A) C(3aA) 1.58(2) yes
C(13aA) C(3aA) 1.49(2) yes
C(4aA) C(4A) 1.51(2) yes
C(5A) C(4aA) 1.41(2) yes
C(8aA) C(4aA) 1.40(2) yes
C(6A) C(5A) 1.38(2) yes
C(6A) O(6'A) 1.403(19) yes
C(6'A) O(6'A) 1.54(3) yes
C(7A) C(6A) 1.38(2) yes
C(7A) O(7'A) 1.41(2) yes
C(7'A) O(7'A) 1.46(3) yes
C(8A) C(7A) 1.40(2) yes
C(8aA) C(8A) 1.38(2) yes
C(8bA) C(8aA) 1.46(2) yes
C(9A) C(8bA) 1.41(2) yes
C(12aA) C(8bA) 1.387(19) yes
C(10A) C(9A) 1.36(2) yes
C(10A) O(10'A) 1.400(19) yes
C(10'A) O(10'A) 1.36(3) yes
C(11A) C(10A) 1.39(2) yes
C(11A) O(11'A) 1.36(2) yes
C(11'A) O(11'A) 1.41(2) yes
C(12A) C(11A) 1.39(2) yes
C(12aA) C(12A) 1.37(2) yes
C(13A) C(12aA) 1.51(2) yes
C(13aA) C(13A) 1.59(2) yes
Cl(1S) C(S) 1.67 yes
Cl(2S) C(S) 1.74 yes
C(9B) Br(B) 1.887(15) yes
C(1B) O(1'B) 1.22(2) yes
O(2B) C(1B) 1.33(3) yes
C(13aB) C(1B) 1.53(3) yes
C(3B) O(2B) 1.40(2) yes
C(3aB) C(3B) 1.58(3) yes
C(4B) C(3aB) 1.58(2) yes
C(13aB) C(3aB) 1.52(2) yes
C(4aB) C(4B) 1.49(2) yes
C(5B) C(4aB) 1.44(2) yes
C(8aB) C(4aB) 1.38(2) yes
C(6B) C(5B) 1.38(2) yes
C(6B) O(6'B) 1.41(2) yes
C(6'B) O(6'B) 1.48(2) yes
C(7B) C(6B) 1.40(2) yes
C(7B) O(7'B) 1.39(2) yes
C(7'B) O(7'B) 1.41(3) yes
C(8B) C(7B) 1.31(2) yes
C(8aB) C(8B) 1.44(2) yes
C(8bB) C(8aB) 1.50(2) yes
C(9B) C(8bB) 1.38(2) yes
C(12aB) C(8bB) 1.39(2) yes
C(10B) C(9B) 1.42(2) yes
C(10B) O(10'B) 1.393(18) yes
C(10'B) O(10'B) 1.49(2) yes
C(11B) C(10B) 1.34(2) yes
C(11B) O(11'B) 1.380(18) yes
C(11'B) O(11'B) 1.44(2) yes
C(12B) C(11B) 1.45(2) yes
C(12aB) C(12B) 1.44(2) yes
C(13B) C(12aB) 1.48(2) yes
C(13aB) C(13A) 1.58(2) yes
