Crystallography Open Database

Information card for entry 2101533

Preview

Coordinates	2101533.cif
Original IUCr paper	HTML

Structure parameters

Chemical name	8-Methyl-8-azabiciclo[3.2.1]oct-3-yl-3,5-dichlorobenzoate (MDL 72222)
Formula	C15 H17 Cl2 N O2
Calculated formula	C15 H17 Cl2 N O2
SMILES	Clc1cc(C(=O)OC2C[C@@H]3N([C@@H](CC3)C2)C)cc(Cl)c1
Title of publication	Stereochemistry of serotonin receptor ligands from crystallographic data. Crystal structures of NAN-190.HBr, 1-phenylbiguanide, MDL 72222 and mianserin.HCl and selectivity criteria towards 5-HT~1~, 5-HT~2~ and 5-HT~3~ receptor subtypes
Authors of publication	Dalpiaz, A.; Ferretti, V.; Gilli, P.; Bertolasi, V.
Journal of publication	Acta Crystallographica Section B
Year of publication	1996
Journal volume	52
Journal issue	3
Pages of publication	509 - 518
a	8.48 ± 0.003 Å
b	9.84 ± 0.003 Å
c	10.158 ± 0.004 Å
α	90.04 ± 0.03°
β	111.77 ± 0.03°
γ	105.07 ± 0.03°
Cell volume	755.6 ± 0.5 Å³
Cell temperature	295 K
Ambient diffraction temperature	295 K
Number of distinct elements	5
Space group number	2
Hermann-Mauguin space group symbol	P -1
Hall space group symbol	-P 1
Residual factor for significantly intense reflections	0.07
Weighted residual factors for significantly intense reflections	0.082
Goodness-of-fit parameter for significantly intense reflections	1.73
Diffraction radiation wavelength	0.71069 Å
Diffraction radiation type	MoKα
Has coordinates	Yes
Has disorder	No
Has F_obs	No

Version history

Revision	Date	Message	Files
176435 (current)	2016-02-14	cif/ (antanas@kurmis) Replacing _[local]_cod_* tags with their equivalents from the COD CIF dictionary in multiple entries from ranges 1, 2.	2101533.cif
134621	2015-04-02	The 'cif_fix_values' script with an option '--fix-only-weighting-scheme' and 'cif_filter' script were run over CIF files which included an incorrect value of the data item '_refine_ls_weighting_scheme'. Read the log for more details. There were more than 18k CIF files with values to modify. Usually these incorrect values include comment with formulas, but values of this data item must be an enumerator. The script creates new data item '_refine_ls_weighting_details' to store these comments with formulas, and writes the enumerator 'calc' as a value of data item '_refine_ls_weighting_scheme'. There exists some exceptions in the script.	2101533.cif
91933	2013-12-28	cif/ (saulius@koala.ibt.lt) Adding DOIs that could be assigned unambiguously to the range 2x CIFs.	2101533.cif
32112	2012-02-03	cif/: committing an update of 45+ thous files, with information appended from the originals.	2101533.cif
26848	2011-09-28	cif/2/, hkl/2/, html/ Reorganising CIFs of the range 2* into the "prefix-directory" tree.	2101533.cif
26029	2011-09-17	cif/2/ Reverting changes of revision 25271: ( cd cif/2/; svn merge -r25271:25270 . ) The problem was that the reprocessed files from IUCr, although were more complete, "resurrected" data errors that were corrected in the previous recisions. The additional data that have been extracted during the reprocessing will have to be merged without overwriting the existing values in COD files, except some explicit and controlled cases (such as publication titles and chemical names).	2101533.cif
25271	2011-09-10	cif/2/ Adding reporocessed IUCr CIFs for the years 1980-2010. The CIFs now contain more complete bibliography, substance names, correctly unfolded text fields (using the CIF line unfolding protocol), explicitely set cell angles, and _cod_data_source_block fields.	2101533.cif
17004	2011-03-31	cif/ Commiting CIFs, that were updated with the 'cif_fix_values' script, using options '--fix-misspelled replacement_values.lst', '--fix-temperature' and '--fix-enums' with built-in table of enum values. The following cmd was used: > (set -x; find ? -name \*.cif \| sort \| xargs -i sh -c 'if !( > cif_fix_values --fix-misspelled ~/../inputs/replacament_values.lst {} \| > cif_filter --add-cif-header {} \| > sponge {} ) 2>&1 \| grep NOTE; then svn revert {}; > fi' ) &	2101533.cif
966	2010-01-30	cif/ Adding _cod_database_code tags to all COD entries. Adding tag description to the cif_cod.dic dictionary so that COD entries can be validated.	2101533.cif
858	2009-11-18	cod/cif/ Changing all _chemical_formula_sum values, were necessary, to conform IUCr recommended syntax and sorting order. After this operation, it will be easier to search for structures using the _chemical_formula_sum values. Only those files and thos lines that really needed to be changed were changed; otehrwise the CIFs were not reformatted. The procedure was as follows: first, all files were passed through a 'cif_filter --parse-formula-sum' command, and the lines containing _cif_formula_sum matching tags were extracted. The extracted tags were "spliced" into the CIF files using the ./bin/{un,}grepciftag commands and awk to filter out old tags and add new tags in their place; the replacement was only done if the new tags contained "_cod_" tags ('grep -q _cod_ tmp-$$'), indicating that cif_filter has altered the formula, or the original file did not contain the _chemical_formula_sum tag ('! grep -q _chemical_formula_sum X'), indicating that cif_filter has guessed the chemical_formula_sum from the file (which should not have happened, actually). If the file was different, disregarding spaces, from the original one ('if ! diff -wb X tmp2-$$'), the original was replaced by the new file, to be committed to the repository. The full command for this step was: ( \ set -x; \ find ? -name \.cif \ \| xargs -n1 -iX \ sh -c 'cif_filter --parse-formula-sum X \ \| ./bin/grepciftag _chemical_formula_sum > tmp-$$; \ if grep -q _cod_ tmp-$$ \|\| ! grep -q _chemical_formula_sum X; \ then \ awk "/^#/,/_chemical_formula_sum/{print} /_chemical_formula_sum/{exit}" X \ \| ./bin/ungrepciftag _chemical_formula_sum > tmp2-$$; \ cat tmp-$$ >> tmp2-$$; \ awk "/_chemical_formula_sum/,/\$eof/" X \ \| ./bin/ungrepciftag _chemical_formula_sum >> tmp2-$$; \ if ! diff -wb X tmp2-$$; \ then \ mv -fv tmp2-$$ X; \ fi; \ fi; \ rm -f tmp-$$ tmp2-$$' \ ) >& sort-chemical-formulae-2009.11.16.log Next, the files were searched that differ from their originals only by the order of CIF tags: svn st \ \| awk '/^M/{print $NF}' \ \| sort \| xargs -n1 -iX \ bash -c 'if diff -q <(svn cat X\|sort) <(sort X) >& /dev/null; \ then echo X; \ fi' \ >& only-reordered.lst These files, after manual inspection ('cat only-reordered.lst \| xargs svn diff \| less'), were reverted to the originals: cat only-reordered.lst \| xargs svn revert Finally, a syntax check was performed using 'vcif': svn st \| awk '/^M/{print $NF}' \ \| sort \| xargs -n1 -iX \ sh -c 'echo -n X"\r"; vcif -l 2048 X \|\| { echo == X == ; echo X >&2; }' \ 2> vcif-check-2009.11.18.err A check on the whole COD archive showed the same files as recorded in vcif-check-2009.11.18.err: find ? -name \.cif \ \| sort \ \| xargs -n1 -iX \ sh -c 'echo -n X"\r"; \ vcif -l 2048 X \|\| { echo == X == ; echo X >&2; }' \ 2> vcif-all-check-`-date`.err diff vcif-check-2009.11.18.err vcif-all-check-2009.11.18.err Since no differences were detected in between vcif-check-2009.11.18.err and vcif-all-check-2009.11.18.err, the latter was deleted and is not committed. The check reveled two broken files, 2/2000267.cif and 2/2001000.cif; these were corrected manually. Afther this, one more 'vcif' check showed no syntax errors, and the changes are committed into the COD repository. 19798 files have modifications in this commit, according to svn st \| grep '^M' \| wc -l	2101533.cif
340	2008-04-05	Fixing CIF files headers in the CIF files from the Acta-Cryst-B/ retrospecive deposition.	2101533.cif
326	2008-04-03	Adding all Acta Cryst. B, C, and E missing retrospective CIF files up to 2008 February, generated from the files that were automatically downloaded from the IUCr site.	2101533.cif