#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/05/2000549.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_2000549
loop_
_publ_author_name
'Flippen-Anderson, J. L.'
'George, C. F.'
_publ_section_title
;
 Absolute configuration of ({-})-\a-acetylmethadol hydrochloride
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1855
_journal_page_last               1857
_journal_paper_doi               10.1107/S0108270192001409
_journal_volume                  48
_journal_year                    1992
_chemical_formula_moiety         'C23 H32 N1 O2,Cl1,H2 O1'
_chemical_formula_sum            'C23 H34 Cl N O3'
_chemical_formula_weight         407.9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90
_cell_angle_beta                 97.71(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.608(4)
_cell_length_b                   8.637(2)
_cell_length_c                   17.273(5)
_cell_volume                     2307.5(10)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.54184
_exptl_absorpt_coefficient_mu    1.64
_exptl_crystal_density_diffrn    1.17
_exptl_crystal_F_000             880
_cod_data_source_file            hh0604.cif
_cod_data_source_block           hh0604_structure_1_of_1
_cod_depositor_comments
;
 Marking attached hydrogen atoms.

 Antanas Vaitkus,
 2017-11-23
;
_cod_original_cell_volume        2307.40(10)
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C23 H34 Cl1 N1 O3'
_cod_database_code               2000549
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
Cl(1) .5984(2) .9202 .5617(2) .084(1) 0
Cl(2) .1510(2) .7455(6) .5248(2) .066(1) 0
C(1) .4723(5) .7399(14) .8074(5) .031(3) 0
C(2) .4361(5) .7518(14) .7199(5) .035(3) 0
C(3) .4014(5) .9088(15) .6890(5) .037(3) 0
N(4) .4169(5) .9277(14) .6053(4) .041(3) 0
C(5) .3909(8) 1.0825(16) .5683(7) .068(5) 0
C(6) .3796(8) .8017(17) .5514(6) .062(5) 0
C(7) .3039(5) .9388(19) .6929(6) .057(4) 0
C(8) .4875(5) .5604(13) .8216(5) .028(3) 0
C(9) .5265(7) .5101(14) .9023(6) .046(4) 0
C(10) .5280(7) .3318(13) .9103(7) .051(4) 0
O(11) .5461(4) .5120(11) .7684(3) .039(2) 0
C(12) .5228(7) .3918(17) .7212(6) .051(5) 0
O(13) .4572(5) .3167(13) .7223(5) .086(4) 0
C(14) .5913(8) .356(2) .6700(8) .100(7) 0
C(15) .5599(5) .8228(13) .8306(5) .031(3) 0
C(16) .6126(5) .8621(14) .7757(6) .045(4) 0
C(17) .6945(6) .9333(17) .7977(7) .061(5) 0
C(18) .7212(6) .9592(16) .8751(7) .061(5) 0
C(19) .6697(6) .9227(16) .9304(6) .054(4) 0
C(20) .5892(6) .8536(13) .9077(6) .036(4) 0
C(21) .4045(5) .7977(14) .8557(5) .030(3) 0
C(22) .3360(5) .7057(15) .8755(5) .042(4) 0
C(23) .2730(6) .7675(18) .9142(6) .055(4) 0
C(24) .2729(6) .9201(18) .9359(6) .052(4) 0
C(25) .3397(6) 1.0123(16) .9185(6) .048(4) 0
C(26) .4024(5) .9586(15) .8789(5) .038(4) 0
C(51) -.0056(5) .6029(14) .7463(5) .029(3) 0
C(52) -.0352(5) .6079(14) .6579(5) .036(4) 0
C(53) -.1228(5) .6924(14) .6298(6) .038(4) 0
N(54) -.1190(5) .7716(14) .5516(5) .048(3) 0
C(55) -.1001(7) .6767(19) .4847(6) .076(6) 0
C(56) -.0557(6) .9076(17) .5609(8) .087(6) 0
C(57) -.2032(6) .5899(18) .6188(7) .071(5) 0
C(58) .0142(5) .7702(14) .7790(5) .032(3) 0
C(59) .0894(6) .8488(14) .7461(6) .047(4) 0
C(60) .0907(9) 1.0251(16) .7620(10) .091(7) 0
O(61) .0369(3) .7578(11) .8613(4) .040(2) 0
C(62) .0037(7) .8528(17) .9098(8) .061(5) 0
O(63) -.0484(5) .9523(13) .8880(5) .079(4) 0
C(64) .0348(8) .8168(19) .9937(7) .079(6)i 0
C(65) -.0786(5) .5282(14) .7838(6) .033(4) 0
C(66) -.0904(6) .3667(15) .7763(6) .044(4) 0
C(67) -.1595(6) .2932(16) .8038(6) .054(5) 0
C(68) -.2174(6) .3752(17) .8400(7) .058(5) 0
C(69) -.2060(7) .5366(18) .8478(7) .061(5) 0
C(70) -.1385(5) .6101(15) .8200(6) .041(4) 0
C(71) .0788(5) .5059(13) .7619(6) .030(3) 0
C(72) .1357(5) .4877(14) .7082(5) .039(4) 0
C(73) .2140(5) .4099(14) .7266(6) .042(4) 0
C(74) .2355(6) .3496(14) .8000(7) .049(4) 0
C(75) .1797(6) .3635(15) .8539(6) .051(4) 0
C(76) .1030(5) .4441(14) .8365(5) .037(3) 0
O(1S) .2550(4) .4247(13) .5398(4) .063(3) 2
O(2S) .7849(6) .0694(16) .6314(6) .126(5) 2
H(2A) .3896 .6786 .7101 .080 0
H(2B) .4816 .7231 .6905 .080 0
H(3A) .4328 .9818 .7238 .080 0
H(4) .493(5) .912(11) .599(4) .050 0
H(5A) .3290 1.0743 .5623 .080 0
H(5B) .4089 1.1099 .5191 .080 0
H(5C) .4095 1.1609 .6062 .080 0
H(6A) .3207 .8314 .5347 .080 0
H(6B) .3807 .7029 .5770 .080 0
H(6C) .4101 .7947 .5068 .080 0
H(7A) .2889 .9506 .7446 .080 0
H(7B) .2663 .8638 .6648 .080 0
H(7C) .2976 1.0364 .6661 .080 0
H(8A) .4310 .5146 .8141 .080 0
H(9A) .5846 .5487 .9125 .080 0
H(9B) .4928 .5526 .9398 .080 0
H(10A) .5531 .3006 .9617 .080 0
H(10B) .5610 .2889 .8724 .080 0
H(10C) .4695 .2950 .9002 .080 0
H(14A) .5747 .2791 .6308 .080 0
H(14B) .6405 .3203 .7047 .080 0
H(14C) .6057 .4506 .6454 .080 0
H(16A) .5940 .8396 .7216 .080 0
H(17A) .7296 .9649 .7589 .080 0
H(18A) .7776 1.0022 .8911 .080 0
H(19A) .6887 .9445 .9845 .080 0
H(20A) .5537 .8268 .9470 .080 0
H(22A) .3333 .5981 .8616 .080 0
H(23A) .2274 .7017 .9269 .080 0
H(24A) .2277 .9616 .9625 .080 0
H(25A) .3416 1.1187 .9347 .080 0
H(26A) .4466 1.0280 .8663 .080 0
H(52A) .0092 .6596 .6342 .080 0
H(52B) -.0405 .5030 .6396 .080 0
H(53A) -.1285 .7630 .6717 .080 0
H(54) -.176(5) .785(12) .536(5) .050 0
H(55A) -.0432 .6347 .4985 .080 0
H(55B) -.1088 .7017 .4300 .080 0
H(55C) -.1423 .6016 .4955 .080 0
H(56A) .0061 .8987 .5700 .080 0
H(56B) -.0753 .9660 .6025 .080 0
H(56C) -.0727 .9595 .5121 .080 0
H(57A) -.2101 .5403 .6673 .080 0
H(57B) -.1956 .5127 .5803 .080 0
H(57C) -.2538 .6504 .6013 .080 0
H(58A) -.0365 .8319 .7642 .080 0
H(59A) .1427 .8054 .7710 .080 0
H(59B) .0841 .8302 .6909 .080 0
H(60A) .1449 1.0674 .7517 .080 0
H(60B) .0817 1.0501 .8145 .080 0
H(60C) .0447 1.0683 .7260 .080 0
H(64A) .0092 .9033 1.0169 .080 0
H(64B) .0965 .8283 1.0007 .080 0
H(64C) .0197 .7227 1.0182 .080 0
H(66A) -.0503 .3066 .7514 .080 0
H(67A) -.1665 .1833 .7977 .080 0
H(68A) -.2645 .3241 .8600 .080 0
H(69A) -.2467 .5961 .8724 .080 0
H(70A) -.1323 .7202 .8259 .080 0
H(72A) .1212 .5301 .6568 .080 0
H(73A) .2524 .3980 .6881 .080 0
H(74A) .2900 .2982 .8136 .080 0
H(75A) .1939 .3169 .9045 .080 0
H(76A) .0657 .4566 .8759 .080 0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C(1) C(2) 1.544(12)
C(1) C(15) 1.548(12)
C(2) C(3) 1.530(16)
C(3) C(7) 1.555(12)
N(4) C(6) 1.498(16)
C(8) O(11) 1.442(11)
O(11) C(12) 1.340(15)
C(12) C(14) 1.508(18)
C(15) C(20) 1.374(13)
C(17) C(18) 1.363(16)
C(19) C(20) 1.398(13)
C(21) C(26) 1.448(17)
C(23) C(24) 1.37(2)
C(25) C(26) 1.348(14)
C(51) C(58) 1.567(16)
C(51) C(71) 1.554(13)
C(53) N(54) 1.522(14)
N(54) C(55) 1.479(17)
C(58) C(59) 1.530(14)
C(59) C(60) 1.547(18)
C(62) O(63) 1.207(16)
C(65) C(66) 1.410(17)
C(66) C(67) 1.389(15)
C(68) C(69) 1.41(2)
C(71) C(72) 1.376(13)
C(72) C(73) 1.393(13)
C(74) C(75) 1.364(15)
C(1) C(8) 1.582(16)
C(1) C(21) 1.518(13)
C(3) N(4) 1.506(11)
N(4) C(5) 1.514(17)
C(8) C(9) 1.509(13)
C(9) C(10) 1.546(17)
C(12) O(13) 1.214(15)
C(15) C(16) 1.379(14)
C(16) C(17) 1.425(14)
C(18) C(19) 1.366(16)
C(21) C(22) 1.409(14)
C(22) C(23) 1.369(15)
C(24) C(25) 1.377(16)
C(51) C(52) 1.535(12)
C(51) C(65) 1.527(13)
C(52) C(53) 1.570(12)
C(53) C(57) 1.526(15)
N(54) C(56) 1.529(17)
C(58) O(61) 1.421(11)
O(61) C(62) 1.327(16)
C(62) C(64) 1.498(17)
C(65) C(70) 1.386(14)
C(67) C(68) 1.363(17)
C(69) C(70) 1.372(16)
C(71) C(76) 1.398(13)
C(73) C(74) 1.370(15)
C(75) C(76) 1.383(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139053389