#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2002104.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_2002104
loop_
_publ_author_name
'Watt, W.'
'Ghosh, R.'
'Seal, T.'
'Mukherjee, B.'
_publ_contact_author
;
    'Watt, William'
    Research Laboratories,
    The Upjohn Company,
    Kalamazoo,
    MI 49007
    USA
;
_publ_section_title
;
 Structure of kopsine: methyl 3-hydroxy-22-oxokopsan-1-carboxylate
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              171
_journal_page_last               173
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C22 H24 N2 O4'
_chemical_formula_weight         380.43
_chemical_name_systematic
;
'Methyl 3-Hydroxy-22-oxokopsan-1-carboxylate'
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.193(3)
_cell_length_b                   11.9660(10)
_cell_length_c                   14.802(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    158
_cell_measurement_theta_max      68
_cell_measurement_theta_min      60
_cell_volume                     1805.4(7)
_computing_cell_refinement
;
performed using the program of Duchamp (1977)
;
_computing_data_reduction        'CRYM (Duchamp, 1984)'
_computing_structure_refinement  'CRYM (Duchamp, 1984)'
_computing_structure_solution
;
MULTAN (Main, Fiske, Hull, Lessinger, Germain, Declercq & Woolfson, 1980)
;
_diffrn_ambient_temperature      158
_diffrn_measurement_device       'Siemens P2~1~'
_diffrn_measurement_method       \q/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            1775
_diffrn_reflns_theta_max         68
_diffrn_reflns_theta_min         1
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 80
_diffrn_standards_number         10
_exptl_absorpt_coefficient_mu    0.699
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.40
_exptl_crystal_description       'chunky block'
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.48
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.32
_refine_ls_abs_structure_details
;
The absolute configuration was established by nmr
(Guggisberg, Gorman, Bycroft \& Schmid, 1969)
;
_refine_ls_goodness_of_fit_all   4.80
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         1772
_refine_ls_R_factor_all          0.047
_refine_ls_R_factor_obs          0.045
_refine_ls_shift/esd_max         0.020
_refine_ls_shift/esd_mean        0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      'calc w = 1/[\s^2^(F^2^)]'
_refine_ls_wR_factor_all         0.123
_refine_ls_wR_factor_obs         0.122
_reflns_number_observed          1689
_reflns_number_total             1775
_reflns_observed_criterion       refl_observed_if_I_>_3.0sigma(I)
_[local]_cod_data_source_file    cd1025.cif
_[local]_cod_data_source_block   cd1025
_cod_database_code               2002104
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C(1) 0.0019(4) 0.0028(2) 0.00160(10) 0.0003(5) -0.0006(3) 0.0006(3)
N(2) 0.0034(3) 0.0030(2) 0.00150(10) -0.0008(4) 0.0006(3) 0.0005(3)
C(1') 0.0076(5) 0.0023(2) 0.0016(2) 0.0007(6) 0.0005(4) -0.0002(3)
O(1') 0.0052(3) 0.0045(2) 0.00270(10) -0.0032(5) 0.0010(3) 0.0027(3)
O(2') 0.0057(3) 0.0037(2) 0.00160(10) 0.0003(4) -0.0008(3) 0.0010(2)
C(3') 0.0076(5) 0.0051(3) 0.0019(2) 0.0018(7) -0.0004(4) 0.0016(4)
C(3) 0.0032(4) 0.0039(3) 0.00200(10) 0.0008(6) 0.0009(4) 0.0009(3)
O(3) 0.0038(3) 0.0048(2) 0.00250(10) 0.0002(4) 0.0021(3) 0.0024(3)
C(4) 0.0045(4) 0.0029(2) 0.0020(2) 0.0002(5) -0.0001(4) 0.0004(3)
C(5) 0.0054(5) 0.0023(2) 0.00180(10) -0.0009(5) -0.0001(4) 0.0003(3)
C(6) 0.0053(5) 0.0035(3) 0.0019(2) -0.0006(6) -0.0016(4) -0.0001(3)
C(7) 0.0057(5) 0.0042(3) 0.0020(2) -0.0015(6) -0.0020(4) 0.0013(3)
C(8) 0.0074(5) 0.0028(2) 0.0018(2) 0.0003(6) -0.0010(4) 0.0011(3)
N(9) 0.0057(4) 0.0024(2) 0.00140(10) 0.0003(4) -0.0001(3) 0.0006(3)
C(10) 0.0058(5) 0.0023(2) 0.0017(2) 0.0007(5) -0.0003(4) 0.0003(3)
C(11) 0.0044(4) 0.0027(2) 0.0018(2) 0.0018(5) -0.0005(4) -0.0001(3)
C(12) 0.0037(4) 0.0022(2) 0.00140(10) 0.0005(5) 0.0004(3) -0.0001(3)
C(13) 0.0034(4) 0.0025(2) 0.00150(10) -0.0012(5) -0.0004(3) -0.0006(3)
C(14) 0.0028(4) 0.0033(2) 0.00200(10) 0.0002(5) 0.0001(4) -0.0002(3)
C(15) 0.0051(5) 0.0039(3) 0.0023(2) -0.0006(6) 0.0006(4) -0.0008(4)
C(16) 0.0049(5) 0.0041(3) 0.0026(2) -0.0008(6) -0.0008(4) -0.0003(4)
C(17) 0.0051(5) 0.0040(3) 0.0019(2) 0.0016(6) -0.0009(4) 0.0005(3)
C(18) 0.0044(4) 0.0028(2) 0.00160(10) -0.0001(5) 0.0000(4) -0.0002(3)
C(19) 0.0038(4) 0.0028(2) 0.00150(10) 0.0006(5) 0.0001(3) 0.0000(3)
C(20) 0.0069(5) 0.0030(2) 0.0020(2) 0.0003(6) -0.0002(4) -0.0003(3)
C(21) 0.0043(4) 0.0024(2) 0.0021(2) -0.0002(5) 0.0007(4) 0.0011(3)
C(22) 0.0040(4) 0.0039(3) 0.00160(10) 0.0030(5) -0.0003(4) 0.0009(3)
O(22) 0.0066(4) 0.0048(2) 0.00210(10) 0.0026(5) 0.0027(3) 0.0000(3)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_thermal_displace_type
C(1) -0.7144(4) -0.2750(3) -0.7167(2) Bani
N(2) -0.8026(3) -0.2595(2) -0.7970(2) Bani
C(1') -0.7707(4) -0.1927(3) -0.8683(2) Bani
O(1') -0.6634(3) -0.1515(2) -0.8814(2) Bani
O(2') -0.8718(3) -0.1789(2) -0.9256(2) Bani
C(3') -0.8381(4) -0.1217(4) -1.0093(2) Bani
C(3) -0.5729(4) -0.3196(3) -0.7328(2) Bani
O(3) -0.4842(3) -0.2575(2) -0.7851(2) Bani
C(4) -0.5120(4) -0.3311(3) -0.6351(2) Bani
C(5) -0.6129(4) -0.3135(3) -0.5580(2) Bani
C(6) -0.5527(4) -0.3416(3) -0.4655(2) Bani
C(7) -0.5334(4) -0.4674(3) -0.4523(2) Bani
C(8) -0.6643(4) -0.5289(3) -0.4669(2) Bani
N(9) -0.7282(3) -0.5037(2) -0.5536(2) Bani
C(10) -0.6677(4) -0.5581(3) -0.6325(2) Bani
C(11) -0.7111(4) -0.4848(3) -0.7132(2) Bani
C(12) -0.7783(4) -0.3786(3) -0.6710(2) Bani
C(13) -0.9195(4) -0.3693(3) -0.6966(2) Bani
C(14) -1.0250(4) -0.4225(3) -0.6591(2) Bani
C(15) -1.1479(4) -0.4039(3) -0.6970(2) Bani
C(16) -1.1618(4) -0.3321(3) -0.7698(2) Bani
C(17) -1.0543(4) -0.2794(3) -0.8094(2) Bani
C(18) -0.9306(4) -0.2998(3) -0.7717(2) Bani
C(19) -0.7373(4) -0.3841(3) -0.5716(2) Bani
C(20) -0.6525(4) -0.1907(3) -0.5646(2) Bani
C(21) -0.7166(4) -0.1688(3) -0.6585(2) Bani
C(22) -0.5970(4) -0.4377(3) -0.7671(2) Bani
O(22) -0.5373(3) -0.4843(2) -0.8266(2) Bani
H(O3) -0.519 -0.251 -0.848 Biso
H(4A) -0.474 -0.407 -0.628 Biso
H(4B) -0.440 -0.274 -0.627 Biso
H(6A) -0.465 -0.303 -0.460 Biso
H(6B) -0.612 -0.312 -0.417 Biso
H(7A) -0.468 -0.495 -0.496 Biso
H(7B) -0.502 -0.481 -0.389 Biso
H(8A) -0.646 -0.611 -0.464 Biso
H(8B) -0.725 -0.507 -0.416 Biso
H(10A) -0.570 -0.558 -0.626 Biso
H(10B) -0.700 -0.636 -0.639 Biso
H(11) -0.773 -0.525 -0.753 Biso
H(14) -1.014 -0.472 -0.605 Biso
H(15) -1.227 -0.442 -0.671 Biso
H(16) -1.251 -0.317 -0.794 Biso
H(17) -1.064 -0.228 -0.862 Biso
H(19) -0.808 -0.352 -0.533 Biso
H(20A) -0.717 -0.173 -0.515 Biso
H(20B) -0.573 -0.141 -0.557 Biso
H(21A) -0.666 -0.108 -0.690 Biso
H(21B) -0.809 -0.145 -0.649 Biso
H(3'A) -0.918 -0.114 -1.047 Biso
H(3'B) -0.803 -0.045 -0.994 Biso
H(3'C) -0.769 -0.165 -1.042 Biso
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.017 0.009 'Cromer \& Liberman, 1970'
H 0 0 'International Tables Vol.IV Table 2.3.1'
N 0.029 0.018 'Cromer \& Liberman, 1970'
O 0.047 0.032 'Cromer \& Liberman, 1970'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
3 0 1
1 1 -6
2 1 4
2 2 0
0 3 1
1 3 5
-2 4 2
1 4 0
0 5 -1
1 5 1
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
N(2) C(1) C(3) 118.4(3) yes
N(2) C(1) C(12) 101.1(3) yes
N(2) C(1) C(21) 109.4(3) yes
C(3) C(1) C(12) 100.5(3) yes
C(3) C(1) C(21) 112.6(3) yes
C(12) C(1) C(21) 114.1(3) yes
C(1) N(2) C(1') 122.8(3) yes
C(1) N(2) C(18) 107.2(3) yes
C(1') N(2) C(18) 127.8(3) yes
N(2) C(1') O(1') 125.1(4) yes
N(2) C(1') O(2') 112.2(3) yes
O(1') C(1') O(2') 122.7(3) yes
C(1') O(2') C(3') 114.4(3) yes
C(1) C(3) O(3) 120.0(3) yes
C(1) C(3) C(4) 104.7(3) yes
C(1) C(3) C(22) 102.7(3) yes
O(3) C(3) C(4) 107.3(3) yes
O(3) C(3) C(22) 114.4(3) yes
C(4) C(3) C(22) 106.7(3) yes
C(3) C(4) C(5) 113.7(3) yes
C(4) C(5) C(6) 111.2(3) yes
C(4) C(5) C(19) 112.1(3) yes
C(4) C(5) C(20) 105.0(3) yes
C(6) C(5) C(19) 109.0(3) yes
C(6) C(5) C(20) 111.8(3) yes
C(19) C(5) C(20) 107.6(3) yes
C(5) C(6) C(7) 112.3(3) yes
C(6) C(7) C(8) 109.9(3) yes
C(7) C(8) N(9) 114.1(3) yes
C(8) N(9) C(10) 114.6(3) yes
C(8) N(9) C(19) 112.9(3) yes
C(10) N(9) C(19) 108.4(3) yes
N(9) C(10) C(11) 104.0(3) yes
C(10) C(11) C(12) 106.0(3) yes
C(10) C(11) C(22) 113.4(3) yes
C(12) C(11) C(22) 104.1(3) yes
C(1) C(12) C(11) 106.7(3) yes
C(1) C(12) C(13) 103.5(3) yes
C(1) C(12) C(19) 109.8(3) yes
C(11) C(12) C(13) 112.3(3) yes
C(11) C(12) C(19) 103.2(3) yes
C(13) C(12) C(19) 120.7(3) yes
C(12) C(13) C(14) 128.4(3) yes
C(12) C(13) C(18) 109.0(3) yes
C(14) C(13) C(18) 122.5(3) yes
C(13) C(14) C(15) 118.1(3) yes
C(14) C(15) C(16) 120.3(4) yes
C(15) C(16) C(17) 121.8(4) yes
C(16) C(17) C(18) 117.6(3) yes
N(2) C(18) C(13) 109.5(3) yes
N(2) C(18) C(17) 130.9(3) yes
C(13) C(18) C(17) 119.6(3) yes
C(5) C(19) N(9) 117.6(3) yes
C(5) C(19) C(12) 109.2(3) yes
N(9) C(19) C(12) 103.6(3) yes
C(5) C(20) C(21) 109.2(3) yes
C(1) C(21) C(20) 110.8(3) yes
C(3) C(22) C(11) 107.1(3) yes
C(3) C(22) O(22) 126.2(3) yes
C(11) C(22) O(22) 126.7(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C(1) N(2) 1.502(5) yes
C(1) C(3) 1.556(5) yes
C(1) C(12) 1.556(5) yes
C(1) C(21) 1.536(5) yes
N(2) C(1') 1.364(5) yes
N(2) C(18) 1.440(5) yes
C(1') O(1') 1.216(5) yes
C(1') O(2') 1.344(5) yes
O(2') C(3') 1.457(5) yes
C(3) O(3) 1.402(5) yes
C(3) C(4) 1.581(5) yes
C(3) C(22) 1.521(5) yes
C(4) C(5) 1.550(5) yes
C(5) C(6) 1.538(5) yes
C(5) C(19) 1.537(5) yes
C(5) C(20) 1.527(5) yes
C(6) C(7) 1.531(6) yes
C(7) C(8) 1.539(6) yes
C(8) N(9) 1.471(5) yes
N(9) C(10) 1.473(5) yes
N(9) C(19) 1.458(5) yes
C(10) C(11) 1.547(5) yes
C(11) C(12) 1.572(5) yes
C(11) C(22) 1.518(5) yes
C(12) C(13) 1.492(5) yes
C(12) C(19) 1.530(5) yes
C(13) C(14) 1.367(5) yes
C(13) C(18) 1.394(5) yes
C(14) C(15) 1.391(6) yes
C(15) C(16) 1.386(5) yes
C(16) C(17) 1.393(6) yes
C(17) C(18) 1.401(6) yes
C(20) C(21) 1.559(5) yes
C(22) O(22) 1.207(5) yes