#------------------------------------------------------------------------------
#$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2001652.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_2001652
loop_
_publ_author_name
'Iwasaki, H.'
'Sugawara, Y.'
'Adachi, T.'
'Morimoto, S.'
'Watanabe, Y.'
_publ_section_title
;
 Structure of 6-<i>O</i>-methylerythromycin A (clarithromycin)
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1227
_journal_page_last               1230
_journal_volume                  49
_journal_year                    1993
_chemical_formula_moiety         'C38 H69 N O13,C H4 O'
_chemical_formula_sum            'C39 H73 N O14'
_chemical_formula_weight         780.01
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_type_scat_source           'IntTabIV Tables 2.2A and 2.2C'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.979(2)
_cell_length_b                   24.115(3)
_cell_length_c                   8.9980(14)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    296
_cell_measurement_theta_max      17.3
_cell_measurement_theta_min      15.2
_cell_volume                     4335.0(10)
_diffrn_measurement_device       'Rigaku AFC-4'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5577
_diffrn_reflns_theta_max         27.5
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      1.189
_exptl_crystal_density_method    'flotation in carbon tetrachloride/n-hexane'
_exptl_crystal_description       Rod
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.27
_refine_ls_goodness_of_fit_obs   0.7823
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     780
_refine_ls_number_reflns         4006
_refine_ls_R_factor_obs          0.045
_refine_ls_shift/esd_max         0.35
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme
; w = 0.5 for |F~o~| < 7.0; 1.0 for 7.0 <= |F~o~| < 25.0; (25.0/|F~o~|)^2^
  for 25.0 <= |F~o~|
;
_refine_ls_wR_factor_obs         0.053
_reflns_number_observed          4006
_reflns_number_total             5577
_reflns_observed_criterion       >3\s(F~o~)
_[local]_cod_data_source_file    oh1013.cif
_[local]_cod_data_source_block   oh1013_structure_1_of_1
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
C(1) .0301(2) .23810(10) .4330(4)
C(2) .0062(2) .29730(10) .4602(4)
C(3) .0107(2) .33130(10) .3132(3)
C(4) .0799(2) .36060(10) .3040(4)
C(5) .1002(2) .37530(10) .1428(4)
C(6) .1362(2) .32700(10) .0553(4)
C(7) .2081(2) .31970(10) .1119(5)
C(8) .2512(2) .2761(2) .0304(5)
C(9) .2319(2) .21690(10) .0700(4)
C(10) .2446(2) .19700(10) .2282(4)
C(11) .1772(2) .18270(10) .2998(4)
C(12) .1786(2) .16970(10) .4677(4)
C(13) .1061(2) .16760(10) .5250(4)
C(14) .0966(2) .14500(10) .6809(4)
C(15) .0231(3) .1399(2) .7206(5)
C(16) -.0650(2) .2933(2) .5218(6)
C(17) .0790(2) .41200(10) .4041(4)
C(18) .1348(2) .3405(2) -.1099(4)
C(19) .3259(2) .2863(2) .0644(8)
C(20) .2946(2) .1483(2) .2211(5)
C(21) .2203(2) .21110(10) .5550(4)
C(22) .0508(3) .2565(2) -.0039(6)
O(1) .00540(10) .20720(10) .3440(3)
O(3) -.04110(10) .37220(10) .3088(3)
O(5) .14860(10) .41970(10) .1427(3)
O(6) .10320(10) .27510(10) .0903(3)
O(9) .2099(2) .18560(10) -.0226(3)
O(11) .14590(10) .13670(10) .2292(3)
O(12) .20880(10) .11660(10) .4939(3)
O(13) .08000(10) .22470(10) .5250(3)
C(1') .1279(2) .47140(10) .0931(4)
C(2') .1802(2) .51420(10) .1396(4)
C(3') .1594(2) .57050(10) .0765(4)
C(4') .1534(2) .56620(10) -.0907(4)
C(5') .1037(2) .52130(10) -.1305(4)
C(6') .0991(2) .5111(2) -.2967(4)
C(7') .1705(2) .66830(10) .1310(6)
C(8') .2680(2) .6162(2) .0640(5)
N(3') .2026(2) .61420(10) .1368(3)
O(2') .1848(2) .51600(10) .2958(3)
O(5') .12360(10) .46950(10) -.0639(3)
C(1") -.0941(2) .36270(10) .2072(4)
C(2") -.1570(2) .39180(10) .2600(4)
C(3") -.1549(2) .45530(10) .2442(4)
C(4") -.1317(2) .46910(10) .0875(4)
C(5") -.0687(2) .43770(10) .0414(4)
C(6") -.0528(2) .4452(2) -.1219(5)
C(7") -.2236(2) .4806(2) .2762(6)
C(8") -.1105(3) .4728(2) .4917(5)
O(3") -.10430(10) .48010(10) .3360(3)
O(4") -.11970(10) .52740(10) .0700(3)
O(5") -.07650(10) .37850(10) .0619(3)
C(23)(SOL) -.0151(3) .0798(2) .1337(6)
O(23)(SOL) .0040(2) .08480(10) .2814(4)
H(2) .039(2) .3150(10) .539(4)
H(3) .0040(10) .3050(10) .232(3)
H(4) .1130(10) .3350(10) .344(3)
H(5) .0620(10) .3860(10) .082(3)
H(7A) .212(2) .3110(10) .230(4)
H(7B) .229(2) .3550(10) .110(3)
H(8) .240(2) .280(2) -.073(4)
H(10) .2610(10) .2290(10) .284(3)
H(11) .1500(10) .2120(10) .288(3)
H(13) .0800(10) .1460(10) .456(3)
H(14A) .116(2) .1070(10) .681(4)
H(14B) .116(2) .170(2) .752(4)
H(15A) -.002(2) .123(2) .642(4)
H(15B) .005(2) .176(2) .756(6)
H(15C) .015(2) .123(2) .806(4)
H(16A) -.068(2) .265(2) .597(5)
H(16B) -.095(2) .278(2) .441(4)
H(16C) -.085(2) .328(2) .555(4)
H(17A) .070(2) .4030(10) .503(4)
H(17B) .122(2) .4330(10) .408(4)
H(17C) .043(2) .439(2) .367(5)
H(18A) .149(2) .310(2) -.161(4)
H(18B) .091(2) .3510(10) -.134(4)
H(18C) .158(2) .375(2) -.132(5)
H(19A) .335(2) .318(2) .017(5)
H(19B) .352(2) .254(2) .010(5)
H(19C) .338(2) .284(2) .185(5)
H(20A) .273(2) .1170(10) .161(4)
H(20B) .304(2) .1390(10) .316(4)
H(20C) .339(2) .163(2) .191(5)
H(21A) .219(2) .2040(10) .661(4)
H(21B) .209(2) .249(2) .534(4)
H(21C) .267(2) .2070(10) .524(4)
H(22A) .031(2) .224(2) .055(5)
H(22B) .063(2) .249(2) -.098(5)
H(22C) .014(2) .286(2) -.009(6)
H(O11) .157(2) .140(2) .136(4)
H(O12) .181(2) .0940(10) .461(4)
H(1') .0830(10) .4820(10) .135(3)
H(2') .229(2) .500(2) .096(5)
H(3') .1160(10) .5780(10) .115(3)
H(4'A) .140(2) .6010(10) -.138(4)
H(4'B) .201(2) .5600(10) -.139(4)
H(5') .0560(10) .5310(10) -.094(3)
H(6'A) .143(2) .498(2) -.343(5)
H(6'B) .067(2) .483(2) -.314(4)
H(6'C) .080(2) .547(2) -.347(4)
H(7'A) .129(2) .6670(10) .175(4)
H(7'B) .198(2) .7000(10) .179(4)
H(7'C) .165(2) .681(2) .014(5)
H(8'A) .298(2) .6420(10) .116(4)
H(8'B) .290(2) .581(2) .072(4)
H(8'C) .263(2) .627(2) -.045(4)
H(O2') .198(2) .548(2) .322(5)
H(1") -.103(2) .3210(10) .197(4)
H(2") -.197(2) .3780(10) .200(4)
H(2"B) -.169(2) .3840(10) .365(4)
H(4") -.1690(10) .4600(10) .014(3)
H(5") -.0300(10) .4500(10) .100(4)
H(6"A) -.048(2) .4820(10) -.137(4)
H(6"B) -.085(2) .428(2) -.178(5)
H(6"C) -.016(2) .421(2) -.153(5)
H(7"A) -.253(2) .467(2) .200(5)
H(7"B) -.238(2) .470(2) .393(4)
H(7"C) -.221(2) .519(2) .280(5)
H(8"A) -.063(2) .489(2) .535(6)
H((8"B) -.119(2) .437(2) .515(6)
H(8"C) -.139(2) .498(2) .547(6)
H(O4") -.090(2) .534(2) .143(5)
H(23A) -.043(2) .1250(10) .108(4)
H(23B) .016(2) .088(2) .069(5)
H(23C) -.056(3) .043(2) .116(7)
H(O23) .008(3) .127(2) .304(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C(1) C(2) 1.526(5) yes
C(1) O(1) 1.200(4) yes
C(1) O(13) 1.335(4) yes
C(2) C(3) 1.558(5) yes
C(2) C(16) 1.529(6) yes
C(3) C(4) 1.554(4) yes
C(3) O(3) 1.430(4) yes
C(4) C(5) 1.548(5) yes
C(4) C(17) 1.533(5) yes
C(5) C(6) 1.579(5) yes
C(5) O(5) 1.444(4) yes
C(6) C(7) 1.534(5) yes
C(6) C(18) 1.523(6) yes
C(6) O(6) 1.448(4) yes
C(7) C(8) 1.545(6) yes
C(8) C(9) 1.521(6) yes
C(8) C(19) 1.543(8) yes
C(9) C(10) 1.523(5) yes
C(9) O(9) 1.207(5) yes
C(10) C(11) 1.531(5) yes
C(10) C(20) 1.544(6) yes
C(11) C(12) 1.543(5) yes
C(11) O(11) 1.423(4) yes
C(12) C(13) 1.539(5) yes
C(12) C(21) 1.519(5) yes
C(12) O(12) 1.435(4) yes
C(13) C(14) 1.516(5) yes
C(13) O(13) 1.474(4) yes
C(14) C(15) 1.518(7) yes
C(22) O(6) 1.419(6) yes
O(3) C(1") 1.417(4) yes
O(5) C(1') 1.387(4) yes
C(1') C(2') 1.525(5) yes
C(1') O(5') 1.415(4) yes
C(2') C(3') 1.530(5) yes
C(2') O(2') 1.409(5) yes
C(3') C(4') 1.513(5) yes
C(3') N(3') 1.467(5) yes
C(4') C(5') 1.512(5) yes
C(5') C(6') 1.519(6) yes
C(5') O(5') 1.443(4) yes
C(7') N(3') 1.454(6) yes
C(8') N(3') 1.461(6) yes
C(1") C(2") 1.517(5) yes
C(1") O(5") 1.406(4) yes
C(2") C(3") 1.538(6) yes
C(3") C(4") 1.520(6) yes
C(3") C(7") 1.529(7) yes
C(3") O(3") 1.436(5) yes
C(4") C(5") 1.527(5) yes
C(4") O(4") 1.435(5) yes
C(5") C(6") 1.515(5) yes
C(5") O(5") 1.447(4) yes
C(8") O(3") 1.417(6) yes
C(23) O(23) 1.388(7) yes
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) O(1) 124.0(3) yes
C(2) C(1) O(13) 111.1(3) yes
O(1) C(1) O(13) 124.8(3) yes
C(1) C(2) C(3) 109.8(3) yes
C(1) C(2) C(16) 106.8(3) yes
C(3) C(2) C(16) 113.2(3) yes
C(2) C(3) C(4) 109.6(3) yes
C(2) C(3) O(3) 110.1(3) yes
C(4) C(3) O(3) 109.2(2) yes
C(3) C(4) C(5) 112.8(3) yes
C(3) C(4) C(17) 109.1(3) yes
C(14) C(13) O(13) 107.0(3) yes
C(13) C(14) C(15) 111.6(4) yes
C(3) O(3) C(1") 116.6(2) yes
C(5) O(5) C(1') 117.9(3) yes
C(6) O(6) C(22) 118.7(3) yes
C(1) O(13) C(13) 119.3(3) yes
O(5) C(1') C(2') 108.4(3) yes
O(5) C(1') O(5') 108.0(3) yes
C(2') C(1') O(5') 109.8(3) yes
C(1') C(2') C(3') 108.2(3) yes
C(1') C(2') O(2') 109.9(3) yes
C(5) C(4) C(17) 111.6(3) yes
C(4) C(5) C(6) 114.7(3) yes
C(4) C(5) O(5) 110.3(3) yes
C(6) C(5) O(5) 104.0(3) yes
C(5) C(6) C(7) 110.3(3) yes
C(5) C(6) C(18) 108.7(3) yes
C(5) C(6) O(6) 108.7(3) yes
C(7) C(6) C(18) 111.4(3) yes
C(7) C(6) O(6) 104.8(3) yes
C(18) C(6) O(6) 112.9(3) yes
C(6) C(7) C(8) 116.3(3) yes
C(7) C(8) C(9) 112.8(3) yes
C(7) C(8) C(19) 109.7(4) yes
C(9) C(8) C(19) 110.4(4) yes
C(8) C(9) C(10) 118.2(3) yes
C(8) C(9) O(9) 121.2(4) yes
C(10) C(9) O(9) 120.6(3) yes
C(9) C(10) C(11) 108.6(3) yes
C(9) C(10) C(20) 107.9(3) yes
C(11) C(10) C(20) 114.5(3) yes
C(10) C(11) C(12) 116.2(3) yes
C(10) C(11) O(11) 112.0(3) yes
C(12) C(11) O(11) 106.7(3) yes
C(11) C(12) C(13) 108.5(3) yes
C(11) C(12) C(21) 112.5(3) yes
C(11) C(12) O(12) 110.5(3) yes
C(13) C(12) C(21) 111.3(3) yes
C(13) C(12) O(12) 108.1(3) yes
C(21) C(12) O(12) 105.8(3) yes
C(12) C(13) C(14) 116.0(3) yes
C(12) C(13) O(13) 107.6(3) yes
C(3') C(2') O(2') 111.1(3) yes
C(2') C(3') C(4') 109.3(3) yes
C(2') C(3') N(3') 110.0(3) yes
C(4') C(3') N(3') 117.6(3) yes
C(3') C(4') C(5') 109.7(3) yes
C(4') C(5') C(6') 112.9(3) yes
C(4') C(5') O(5') 109.9(3) yes
C(6') C(5') O(5') 106.6(3) yes
C(3') N(3') C(7') 111.8(3) yes
C(3') N(3') C(8') 112.6(3) yes
C(7') N(3') C(8') 110.5(3) yes
C(1') O(5') C(5') 113.7(3) yes
O(3) C(1") C(2") 109.9(3) yes
O(3) C(1") O(5") 111.7(3) yes
C(2") C(1") O(5") 111.9(3) yes
C(1") C(2") C(3") 114.2(3) yes
C(2") C(3") C(4") 108.2(3) yes
C(2") C(3") C(7") 110.9(4) yes
C(2") C(3") O(3") 112.3(3) yes
C(4") C(3") C(7") 111.1(4) yes
C(4") C(3") O(3") 103.2(3) yes
C(7") C(3") O(3") 110.9(3) yes
C(3") C(4") C(5") 113.2(3) yes
C(3") C(4") O(4") 111.6(3) yes
C(5") C(4") O(4") 108.6(3) yes
C(4") C(5") C(6") 112.1(3) yes
C(4") C(5") O(5") 111.5(3) yes
C(6") C(5") O(5") 105.3(3) yes
C(3") O(3") C(8") 117.1(3) yes
C(1") O(5") C(5") 114.4(3) yes
_cod_database_code 2001652