Crystallography Open Database

Information card for entry 7151514

Preview

Coordinates	7151514.cif
Original paper (by DOI)	HTML

Structure parameters

Chemical name	tert-butyl(1RS,2SR,3RS)-3-methyl-2-(N,N-dibenzylamino)- cyclopentane-1-carboxylate
Formula	C25 H33 N O2
Calculated formula	C25 H33 N O2
SMILES	O(C(=O)[C@H]1[C@@H](N(Cc2ccccc2)Cc2ccccc2)[C@H](C)CC1)C(C)(C)C.O(C(=O)[C@@H]1[C@H](N(Cc2ccccc2)Cc2ccccc2)[C@@H](C)CC1)C(C)(C)C
Title of publication	Asymmetric synthesis of (1R,2S,3R)-3-methylcispentacin and (1S,2S,3R)-3-methyltranspentacin by kinetic resolution of tert-butyl (±)-3-methylcyclopentene-1-carboxylate
Authors of publication	Bunnage, Mark E.; Chippindale, Ann M.; Davies, Stephen G.; Parkin, Richard M.; Smith, Andrew D.; Withey, Jonathan M.
Journal of publication	Organic & Biomolecular Chemistry
Year of publication	2003
Journal volume	1
Journal issue	21
Pages of publication	3698 - 3707
a	11.289 ± 0.001 Å
b	11.4013 ± 0.0008 Å
c	19.344 ± 0.004 Å
α	96.03 ± 0.01°
β	95.87 ± 0.01°
γ	112.82 ± 0.007°
Cell volume	2254.2 ± 0.6 Å³
Cell temperature	293 K
Ambient diffraction temperature	293 K
Number of distinct elements	4
Space group number	2
Hermann-Mauguin space group symbol	P -1
Hall space group symbol	-P 1
Residual factor for significantly intense reflections	0.0596
Weighted residual factors for all reflections included in the refinement	0.0669
Goodness-of-fit parameter for all reflections included in the refinement	1.0356
Diffraction radiation wavelength	1.5418 Å
Diffraction radiation type	CuKα
Has coordinates	Yes
Has disorder	No
Has F_obs	No

Version history

Revision	Date	Message	Files
297230 (current)	2025-01-08	Updated bibliography in entries 7151514-7151515.	7151514.cif
211332	2018-10-05	cif/ Fixing enumeration values for CIF data items _atom_sites_solution_* using cif_fix_values. Data item relocations and exclusion of CIF comment lines might have occurred due to the usage of cif_filter.	7151514.cif
176453	2016-02-16	cif/ (antanas@kurmis) Replacing _[local]_cod_* tags with their equivalents from the COD CIF dictionary in multiple entries in range 7.	7151514.cif
129439	2015-01-07	cod/ (robertas@burundukas) Correcting values of _exptl_crystal_density_meas and _exptl_crystal_density_method data items: codsql "select codid from validation where message like '%\\'_exptl_crystal_density_meas\\' value \"not measured\" is %'" -NB \ \| codid2file \ \| xargs perl -i -pe "s/_exptl_crystal_density_meas\\s+'not +measured'/_exptl_crystal_density_meas ?/i; \ s/_exptl_crystal_density_method\\s+('not +measured'\|\\?\|none)/_exptl_crystal_density_method ./i"	7151514.cif
120443	2014-07-15	Adding 17924 DOIs guessed from source file names.	7151514.cif
75803	2013-03-13	smi/7 Adding SMILES removing chiral marks and spurious H-atoms from compounds in non-chiral groups.	7151514.cif
35909	2012-02-26	cif/7/: reorganising range 7 into a prefix-directory tree.	7151514.cif
11752	2011-02-18	cif/7/ Redepositing RSC CIFs that were formally processed with an old version of cif_fix_values script.	7151514.cif
5312	2011-01-03	cif/ Adding files, updated with the 'cif_fix_enum' program and the cif_core.dic dictionary. The enumerator values were fixed, mostly incorrect case, but also some values that had extra underscores, dashes or spaces. Unfortunately, 22 had non-ASCII characters with the 8-th bit set, and these got incorrectly interpreted as latin1 characters and converted to their UTF8 equivalents by Perl. To fix the structures, however, they need to be redeposited from the original files with the new CIFParser/cif_filter version.	7151514.cif
3890	2010-12-07	cif/7/ Adding CIFs with data extracted from New-J-Chem-2004-2000/, Org-Biomol-Chem-2004-2000/ and RSC-2004-2000/.	7151514.cif