#------------------------------------------------------------------------------
#$Date: 2014-07-11 22:06:05 +0100 (Fri, 11 Jul 2014) $
#$Revision: 120077 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/64/4116434.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4116434
loop_
_publ_author_name
'John L. Wood'
'Alexandra A. Holubec'
'Brian M. Stoltz'
'Matthew M. Weiss'
'Julie A. Dixon'
'Brian D. Doan'
'Mohammed F. Shamji'
'Jennifer M. Chen'
'Timothy P. Heffron'
_publ_contact_author
;
John L. Wood
Yale University
Department of Chemistry
P.O. Box 208107
New Haven, CT  06520-8107
;
_publ_contact_author_email       ' john.wood@quickmail.yale.edu'
_publ_contact_author_fax         ' (203)432-6144 '
_publ_contact_author_phone       ' (203)432-5991 '
_publ_section_title
;
 Application of Reactive Enols in Synthesis: A Versatile, Efficient, and
 Stereoselective Construction of the Welwitindolinone Carbon Skeleton
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6326
_journal_page_last               6327
_journal_volume                  121
_journal_year                    1999
_chemical_formula_moiety         'C22 H27 N O4 '
_chemical_formula_sum            'C22 H27 N O4'
_chemical_formula_weight         369.46
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_date             'Fri Sep 11 13:06:00 1998'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                90
_cell_angle_beta                 104.98(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1123(3)
_cell_length_b                   12.437(1)
_cell_length_c                   15.961(1)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    183.2
_cell_measurement_theta_max      0.0
_cell_measurement_theta_min      0.0
_cell_volume                     1939.1(2)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        teXsan
_computing_publication_material  teXsan
_computing_structure_refinement  teXsan
_diffrn_ambient_temperature      183.2
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'CCD data frame'
_diffrn_orient_matrix_UB_11      0.00000
_diffrn_orient_matrix_UB_12      0.00000
_diffrn_orient_matrix_UB_13      0.00000
_diffrn_orient_matrix_UB_21      0.00000
_diffrn_orient_matrix_UB_22      0.00000
_diffrn_orient_matrix_UB_23      0.00000
_diffrn_orient_matrix_UB_31      0.00000
_diffrn_orient_matrix_UB_32      0.00000
_diffrn_orient_matrix_UB_33      0.00000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoKalpha
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.00
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4067
_diffrn_reflns_theta_max         26.39
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            cut-block
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       colorless
_exptl_crystal_F_000             792.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.450
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.22
_refine_ls_extinction_coef       15.48561
_refine_ls_extinction_method     Zachariasen_type_2_Gaussian_isotropic
_refine_ls_goodness_of_fit_obs   2.556
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3010
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0471
_refine_ls_shift/esd_max         0.0002
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_obs         0.0648
_reflns_number_observed          3010
_reflns_number_total             4067
_reflns_observed_criterion       3.00
_[local]_cod_data_source_file    ja991022s_2.cif
_[local]_cod_data_source_block   compound_xii
_[local]_cod_cif_authors_sg_H-M  'P 21/a '
_[local]_cod_chemical_formula_sum_orig 'C22 H27 N O4 '
_cod_original_cell_volume        1939.2(2)
_cod_database_code               4116434
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'1/2-x,1/2+y,   -z'
'   -x,   -y,   -z'
'1/2+x,1/2-y,   +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
O(1) 0.0383(7) 0.0431(9) 0.0454(8) 0.0062(6) 0.0180(6) 0.0104(6)
O(2) 0.0246(6) 0.0352(7) 0.0338(6) -0.0030(5) 0.0061(4) -0.0042(5)
O(3) 0.0304(6) 0.0366(8) 0.0559(8) 0.0080(5) 0.0059(5) -0.0038(6)
O(4) 0.0490(7) 0.0346(8) 0.0381(7) 0.0037(6) 0.0121(5) -0.0066(6)
N(1) 0.0311(8) 0.0379(10) 0.0396(8) -0.0058(7) 0.0060(6) 0.0084(7)
C(1) 0.0323(9) 0.034(1) 0.0356(9) -0.0036(8) -0.0012(7) 0.0072(9)
C(2) 0.041(1) 0.033(1) 0.051(1) -0.0086(9) -0.0057(8) 0.0081(10)
C(3) 0.049(1) 0.026(1) 0.053(1) -0.0004(9) -0.0098(9) 0.0006(9)
C(4) 0.0399(10) 0.028(1) 0.044(1) 0.0066(8) -0.0031(8) -0.0011(9)
C(5) 0.0295(9) 0.029(1) 0.0359(9) 0.0041(7) -0.0023(7) -0.0004(8)
C(6) 0.0305(8) 0.026(1) 0.0329(9) -0.0006(7) -0.0028(7) 0.0045(8)
C(7) 0.0292(9) 0.026(1) 0.0320(9) -0.0003(7) 0.0050(7) 0.0033(8)
C(8) 0.0319(9) 0.035(1) 0.0302(9) 0.0006(8) 0.0047(7) 0.0093(8)
C(9) 0.042(1) 0.057(2) 0.058(1) -0.0134(9) 0.0131(9) 0.011(1)
C(10) 0.0321(8) 0.029(1) 0.0292(9) -0.0030(7) 0.0051(6) 0.0031(8)
C(11) 0.0451(10) 0.040(1) 0.0327(9) -0.0049(9) 0.0112(7) -0.0004(9)
C(12) 0.0349(9) 0.041(1) 0.0349(9) -0.0024(8) 0.0007(7) 0.0056(8)
C(13) 0.0294(8) 0.0233(10) 0.0300(9) 0.0000(7) 0.0084(6) 0.0009(7)
C(14) 0.0240(8) 0.0269(10) 0.0321(9) -0.0007(7) 0.0055(6) -0.0018(8)
C(15) 0.0295(9) 0.032(1) 0.0360(10) 0.0044(7) 0.0061(7) -0.0038(8)
C(16) 0.0392(9) 0.036(1) 0.0329(9) 0.0016(8) 0.0089(7) -0.0026(9)
C(17) 0.0295(8) 0.034(1) 0.0249(8) -0.0004(7) 0.0063(6) -0.0018(8)
C(18) 0.0332(9) 0.034(1) 0.0323(9) -0.0018(7) 0.0026(7) -0.0024(8)
C(19) 0.0307(9) 0.035(1) 0.0297(9) -0.0006(7) 0.0077(6) -0.0022(8)
C(20) 0.0350(9) 0.041(1) 0.0339(9) -0.0011(8) 0.0103(7) 0.0054(9)
C(21) 0.054(1) 0.038(1) 0.049(1) 0.0023(9) 0.0166(9) 0.0109(10)
C(22) 0.066(1) 0.056(2) 0.037(1) -0.007(1) 0.0044(9) 0.010(1)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
O(1) -0.1615(1) -0.1489(1) -0.37814(7) 0.0409(4) Uij
O(2) -0.64204(10) -0.18756(10) -0.25923(7) 0.0314(3) Uij
O(3) -0.6784(1) 0.0137(1) -0.25830(8) 0.0420(4) Uij
O(4) -0.5171(1) -0.0071(1) -0.12718(7) 0.0404(4) Uij
N(1) -0.1828(1) 0.0317(1) -0.35412(9) 0.0368(4) Uij
C(1) -0.2656(2) 0.0977(2) -0.3157(1) 0.0357(5) Uij
C(2) -0.2464(2) 0.2016(2) -0.2858(1) 0.0449(6) Uij
C(3) -0.3311(2) 0.2379(2) -0.2354(1) 0.0468(6) Uij
C(4) -0.4278(2) 0.1720(2) -0.2142(1) 0.0399(5) Uij
C(5) -0.4489(2) 0.0673(1) -0.2470(1) 0.0335(5) Uij
C(6) -0.3713(2) 0.0342(1) -0.30180(10) 0.0319(5) Uij
C(7) -0.3614(2) -0.0723(1) -0.3377(1) 0.0297(5) Uij
C(8) -0.2257(2) -0.0727(2) -0.3585(1) 0.0331(5) Uij
C(9) -0.0560(2) 0.0655(2) -0.3731(1) 0.0521(6) Uij
C(10) -0.4878(2) -0.1296(1) -0.39996(10) 0.0308(5) Uij
C(11) -0.4588(2) -0.2069(2) -0.4660(1) 0.0389(5) Uij
C(12) -0.6170(2) -0.0651(2) -0.4348(1) 0.0385(5) Uij
C(13) -0.4375(2) -0.1624(1) -0.30720(10) 0.0275(4) Uij
C(14) -0.5107(1) -0.1361(1) -0.23735(10) 0.0280(4) Uij
C(15) -0.5412(2) -0.0142(1) -0.2195(1) 0.0328(5) Uij
C(16) -0.5023(2) -0.1135(2) -0.0906(1) 0.0363(5) Uij
C(17) -0.4271(2) -0.1759(1) -0.14655(10) 0.0296(5) Uij
C(18) -0.2776(2) -0.1369(2) -0.1274(1) 0.0344(5) Uij
C(19) -0.4318(2) -0.2972(2) -0.1425(1) 0.0317(5) Uij
C(20) -0.3843(2) -0.3638(2) -0.0762(1) 0.0363(5) Uij
C(21) -0.3884(2) -0.4828(2) -0.0904(1) 0.0467(6) Uij
C(22) -0.3207(2) -0.3304(2) 0.0150(1) 0.0547(7) Uij
H(1) -0.1785 0.2467 -0.2988 0.0539 Uij
H(2) -0.3223 0.3100 -0.2151 0.0561 Uij
H(3) -0.4803 0.1981 -0.1770 0.0479 Uij
H(4) 0.0133 0.0733 -0.3204 0.0625 Uij
H(5) -0.0285 0.0129 -0.4083 0.0625 Uij
H(6) -0.0699 0.1323 -0.4030 0.0625 Uij
H(7) -0.3729 -0.2407 -0.4428 0.0467 Uij
H(8) -0.5288 -0.2599 -0.4795 0.0467 Uij
H(9) -0.4566 -0.1687 -0.5171 0.0467 Uij
H(10) -0.6317 -0.0190 -0.3906 0.0462 Uij
H(11) -0.6080 -0.0231 -0.4827 0.0462 Uij
H(12) -0.6927 -0.1125 -0.4529 0.0462 Uij
H(13) -0.3897 -0.2289 -0.2988 0.0330 Uij
H(14) -0.6491 -0.2437 -0.3065 0.0448 Uij
H(15) -0.7263 -0.0605 -0.2666 0.0448 Uij
H(16) -0.4501 -0.1119 -0.0318 0.0435 Uij
H(17) -0.5893 -0.1446 -0.0939 0.0435 Uij
H(18) -0.2760 -0.0607 -0.1312 0.0413 Uij
H(19) -0.2295 -0.1588 -0.0707 0.0413 Uij
H(20) -0.2352 -0.1672 -0.1686 0.0413 Uij
H(21) -0.4755 -0.3313 -0.1957 0.0381 Uij
H(22) -0.4348 -0.4981 -0.1490 0.0560 Uij
H(23) -0.4354 -0.5161 -0.0529 0.0560 Uij
H(24) -0.2976 -0.5100 -0.0784 0.0560 Uij
H(25) -0.3240 -0.2544 0.0193 0.0656 Uij
H(26) -0.3695 -0.3621 0.0522 0.0656 Uij
H(27) -0.2281 -0.3537 0.0316 0.0656 Uij
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 88 0.003 0.002 'International Tables'
H 0 108 0.000 0.000 'International Tables'
N 0 4 0.006 0.003 'International Tables'
O 0 16 0.011 0.006 'International Tables'
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(15) O(4) C(16) 109.4(1) yes
C(1) N(1) C(8) 110.9(1) yes
C(1) N(1) C(9) 125.0(2) yes
C(8) N(1) C(9) 123.4(2) yes
N(1) C(1) C(2) 130.4(2) yes
N(1) C(1) C(6) 107.6(2) yes
C(2) C(1) C(6) 121.5(2) yes
C(1) C(2) C(3) 116.9(2) yes
C(2) C(3) C(4) 121.9(2) yes
C(3) C(4) C(5) 120.6(2) yes
C(4) C(5) C(6) 117.3(2) yes
C(4) C(5) C(15) 124.0(2) yes
C(6) C(5) C(15) 118.4(2) yes
C(1) C(6) C(5) 121.1(2) yes
C(1) C(6) C(7) 108.6(1) yes
C(5) C(6) C(7) 129.0(2) yes
C(6) C(7) C(8) 104.5(1) yes
C(6) C(7) C(10) 122.2(1) yes
C(6) C(7) C(13) 117.1(1) yes
C(8) C(7) C(10) 120.1(1) yes
C(8) C(7) C(13) 130.1(1) yes
C(10) C(7) C(13) 57.9(1) yes
O(1) C(8) N(1) 124.2(2) yes
O(1) C(8) C(7) 129.3(2) yes
N(1) C(8) C(7) 106.5(1) yes
C(7) C(10) C(11) 117.2(1) yes
C(7) C(10) C(12) 118.4(2) yes
C(7) C(10) C(13) 58.97(10) yes
C(11) C(10) C(12) 112.8(1) yes
C(11) C(10) C(13) 116.1(1) yes
C(12) C(10) C(13) 123.4(1) yes
C(7) C(13) C(10) 63.1(1) yes
C(7) C(13) C(14) 117.5(1) yes
C(10) C(13) C(14) 124.1(1) yes
O(2) C(14) C(13) 108.7(1) yes
O(2) C(14) C(15) 105.0(1) yes
O(2) C(14) C(17) 109.3(1) yes
C(13) C(14) C(15) 119.3(1) yes
C(13) C(14) C(17) 111.3(1) yes
C(15) C(14) C(17) 102.7(1) yes
O(3) C(15) O(4) 108.8(1) yes
O(3) C(15) C(5) 108.5(1) yes
O(3) C(15) C(14) 111.8(1) yes
O(4) C(15) C(5) 107.6(1) yes
O(4) C(15) C(14) 104.7(1) yes
C(5) C(15) C(14) 115.1(1) yes
O(4) C(16) C(17) 104.2(1) yes
C(14) C(17) C(16) 98.6(1) yes
C(14) C(17) C(18) 110.7(1) yes
C(14) C(17) C(19) 109.9(1) yes
C(16) C(17) C(18) 109.6(1) yes
C(16) C(17) C(19) 117.2(1) yes
C(18) C(17) C(19) 110.2(1) yes
C(17) C(19) C(20) 130.2(2) yes
C(19) C(20) C(21) 120.3(2) yes
C(19) C(20) C(22) 125.4(2) yes
C(21) C(20) C(22) 114.3(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(8) 1.234(2) yes
O(2) C(14) 1.434(2) yes
O(3) C(15) 1.409(2) yes
O(4) C(15) 1.433(2) yes
O(4) C(16) 1.438(2) yes
N(1) C(1) 1.420(2) yes
N(1) C(8) 1.365(2) yes
N(1) C(9) 1.454(2) yes
C(1) C(2) 1.374(3) yes
C(1) C(6) 1.393(2) yes
C(2) C(3) 1.393(3) yes
C(3) C(4) 1.383(3) yes
C(4) C(5) 1.399(2) yes
C(5) C(6) 1.381(2) yes
C(5) C(15) 1.518(3) yes
C(6) C(7) 1.456(2) yes
C(7) C(8) 1.492(2) yes
C(7) C(10) 1.572(2) yes
C(7) C(13) 1.510(2) yes
C(10) C(11) 1.510(3) yes
C(10) C(12) 1.512(2) yes
C(10) C(13) 1.493(2) yes
C(13) C(14) 1.524(2) yes
C(14) C(15) 1.588(3) yes
C(14) C(17) 1.558(2) yes
C(16) C(17) 1.527(2) yes
C(17) C(18) 1.541(2) yes
C(17) C(19) 1.511(3) yes
C(19) C(20) 1.332(2) yes
C(20) C(21) 1.497(3) yes
C(20) C(22) 1.490(3) yes
_journal_paper_doi 10.1021/ja991022s