#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:02:04 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178882 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/11/4111184.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_4111184
loop_
_publ_author_name
'Robert B. Lettan'
'Troy E. Reynolds'
'Chris V. Galliford'
'Karl A. Scheidt'
_publ_contact_author_address
;Department of Chemistry
Northwestern University
215 Sheridan Road
Evanston, IL 60208
;
_publ_contact_author_email       scheidt@northwestern.edu
_publ_contact_author_name        'Karl Scheidt'
_publ_section_title
;
 Synthesis of Tertiary β-Hydroxy Amides by Enolate Additions to
 Acylsilanes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15566
_journal_page_last               15567
_journal_paper_doi               10.1021/ja065605v
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C30 H35 N O3'
_chemical_formula_weight         457.59
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.728(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.3593(11)
_cell_length_b                   9.6066(9)
_cell_length_c                   12.1731(12)
_cell_measurement_reflns_used    4450
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.50
_cell_measurement_theta_min      2.77
_cell_volume                     1250.4(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11483
_diffrn_reflns_theta_full        28.67
_diffrn_reflns_theta_max         28.67
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.7(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         5736
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0803P)²+0.0250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1090
_reflns_number_gt                5349
_reflns_number_total             5736
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja065605vrom20060802_063713.cif
_cod_data_source_block           amide22
_cod_database_code               4111184
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
H7 H 0.896(2) 0.330(3) 0.652(2) 0.058(7) Uiso 1 1 d
C30 C 0.33270(15) 0.39534(18) -0.11192(12) 0.0326(3) Uani 1 1 d
O1 O 0.47646(10) 0.00046(11) 0.27230(10) 0.0311(2) Uani 1 1 d
O3 O 0.19507(9) 0.50765(11) -0.02966(8) 0.0284(2) Uani 1 1 d
O2 O 0.42436(10) 0.16250(11) 0.08278(8) 0.0300(2) Uani 1 1 d
N N 0.34814(10) 0.37578(12) 0.09921(9) 0.0229(2) Uani 1 1 d
C16 C 0.41851(12) 0.26320(14) 0.14465(11) 0.0235(3) Uani 1 1 d
C15 C 0.49017(12) 0.25482(14) 0.27556(11) 0.0235(3) Uani 1 1 d
C17 C 0.34577(12) 0.51037(14) 0.15597(11) 0.0240(3) Uani 1 1 d
C1 C 0.45097(12) 0.12227(14) 0.32706(11) 0.0245(3) Uani 1 1 d
C9 C 0.31085(12) 0.13198(14) 0.31011(11) 0.0261(3) Uani 1 1 d
C3 C 0.66845(13) 0.12684(16) 0.49131(12) 0.0291(3) Uani 1 1 d
C28 C 0.26279(12) 0.38064(15) -0.02531(11) 0.0258(3) Uani 1 1 d
C29 C 0.17306(15) 0.25689(17) -0.05664(14) 0.0338(3) Uani 1 1 d
C10 C 0.22523(14) 0.05048(16) 0.22629(14) 0.0335(3) Uani 1 1 d
C20 C 0.63403(14) 0.46453(16) 0.14193(13) 0.0293(3) Uani 1 1 d
C2 C 0.52878(13) 0.10800(16) 0.45834(12) 0.0295(3) Uani 1 1 d
C24 C 0.64439(14) 0.57551(17) 0.32157(13) 0.0328(3) Uani 1 1 d
C14 C 0.26549(13) 0.22692(16) 0.37309(13) 0.0300(3) Uani 1 1 d
C23 C 0.75908(15) 0.5129(2) 0.37733(13) 0.0379(4) Uani 1 1 d
C19 C 0.57901(12) 0.55026(15) 0.20372(12) 0.0270(3) Uani 1 1 d
C26 C 0.11735(14) 0.48936(18) 0.13530(15) 0.0324(3) Uani 1 1 d
C21 C 0.74951(14) 0.40251(18) 0.19789(14) 0.0342(3) Uani 1 1 d
C4 C 0.74135(15) 0.04037(18) 0.44686(14) 0.0355(3) Uani 1 1 d
C13 C 0.13769(15) 0.23585(19) 0.35482(14) 0.0362(3) Uani 1 1 d
C11 C 0.09726(15) 0.06113(19) 0.20712(15) 0.0392(4) Uani 1 1 d
C7 C 0.85693(16) 0.2520(2) 0.60086(15) 0.0425(4) Uani 1 1 d
C18 C 0.44943(13) 0.60997(15) 0.14715(13) 0.0282(3) Uani 1 1 d
C6 C 0.92738(16) 0.1667(2) 0.55624(16) 0.0436(4) Uani 1 1 d
C8 C 0.72766(15) 0.23255(19) 0.56778(13) 0.0367(3) Uani 1 1 d
C25 C 0.21077(13) 0.55746(15) 0.08663(12) 0.0265(3) Uani 1 1 d
C5 C 0.86976(16) 0.0622(2) 0.47853(15) 0.0420(4) Uani 1 1 d
C12 C 0.05359(15) 0.1526(2) 0.27201(15) 0.0392(4) Uani 1 1 d
C22 C 0.81160(15) 0.42549(19) 0.31563(15) 0.0383(4) Uani 1 1 d
C27 C 0.19042(16) 0.71358(16) 0.07756(15) 0.0349(3) Uani 1 1 d
H10 H 0.2513(19) -0.013(2) 0.1788(18) 0.038(5) Uiso 1 1 d
H24 H 0.607(2) 0.643(2) 0.3649(18) 0.039(5) Uiso 1 1 d
H20 H 0.5886(17) 0.4480(19) 0.0628(16) 0.026(4) Uiso 1 1 d
H14 H 0.3225(17) 0.2947(19) 0.4255(16) 0.025(4) Uiso 1 1 d
H181 H 0.4428(16) 0.689(2) 0.1832(15) 0.021(4) Uiso 1 1 d
H4 H 0.700(2) -0.031(2) 0.3908(18) 0.038(5) Uiso 1 1 d
H182 H 0.4336(16) 0.626(2) 0.0634(16) 0.030(4) Uiso 1 1 d
H21 H 0.788(2) 0.339(3) 0.156(2) 0.048(6) Uiso 1 1 d
H5 H 0.919(2) 0.005(2) 0.4466(18) 0.039(5) Uiso 1 1 d
H1 H 0.462(2) 0.032(3) 0.195(2) 0.055(6) Uiso 1 1 d
H222 H 0.5080(16) 0.0195(19) 0.4799(15) 0.023(4) Uiso 1 1 d
H152 H 0.5831(18) 0.249(2) 0.2848(16) 0.031(4) Uiso 1 1 d
H151 H 0.4801(16) 0.3396(18) 0.3195(15) 0.023(4) Uiso 1 1 d
H17 H 0.3565(16) 0.4977(19) 0.2392(15) 0.025(4) Uiso 1 1 d
H211 H 0.4959(17) 0.1795(18) 0.5041(16) 0.023(4) Uiso 1 1 d
H12 H -0.036(2) 0.164(3) 0.261(2) 0.056(6) Uiso 1 1 d
H23 H 0.803(2) 0.530(3) 0.464(2) 0.054(6) Uiso 1 1 d
H6 H 1.011(2) 0.180(3) 0.574(2) 0.055(6) Uiso 1 1 d
H22 H 0.895(2) 0.389(2) 0.3579(18) 0.043(5) Uiso 1 1 d
H11 H 0.039(2) 0.005(2) 0.1485(19) 0.044(5) Uiso 1 1 d
H8 H 0.678(2) 0.299(2) 0.602(2) 0.047(6) Uiso 1 1 d
H13 H 0.113(2) 0.304(2) 0.400(2) 0.045(6) Uiso 1 1 d
H262 H 0.1330(18) 0.392(2) 0.1459(16) 0.034(5) Uiso 1 1 d
H303 H 0.387(2) 0.485(3) -0.0981(19) 0.047(6) Uiso 1 1 d
H273 H 0.105(2) 0.733(2) 0.0259(18) 0.039(5) Uiso 1 1 d
H292 H 0.2133(19) 0.171(2) -0.0645(18) 0.038(5) Uiso 1 1 d
H261 H 0.036(2) 0.498(2) 0.0815(19) 0.041(5) Uiso 1 1 d
H302 H 0.2749(19) 0.402(2) -0.1884(18) 0.038(5) Uiso 1 1 d
H263 H 0.1233(18) 0.535(2) 0.2077(18) 0.033(5) Uiso 1 1 d
H271 H 0.2530(19) 0.758(2) 0.0518(17) 0.035(5) Uiso 1 1 d
H301 H 0.383(2) 0.313(2) -0.1098(18) 0.037(5) Uiso 1 1 d
H293 H 0.1346(18) 0.245(2) 0.0029(17) 0.034(4) Uiso 1 1 d
H272 H 0.208(2) 0.752(2) 0.161(2) 0.050(6) Uiso 1 1 d
H291 H 0.105(2) 0.282(2) -0.128(2) 0.053(6) Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C28 O3 C25 110.96(10)
C16 N C17 127.97(11)
C16 N C28 122.11(11)
C17 N C28 109.85(10)
O2 C16 N 121.48(12)
O2 C16 C15 118.23(12)
N C16 C15 120.26(11)
C16 C15 C1 109.92(11)
N C17 C25 99.95(10)
N C17 C18 112.07(11)
C25 C17 C18 114.72(11)
O1 C1 C9 110.61(11)
O1 C1 C2 105.95(11)
C9 C1 C2 110.37(10)
O1 C1 C15 110.75(10)
C9 C1 C15 108.77(10)
C2 C1 C15 110.38(11)
C10 C9 C14 118.33(13)
C10 C9 C1 120.06(13)
C14 C9 C1 121.53(12)
C8 C3 C4 118.42(14)
C8 C3 C2 119.57(13)
C4 C3 C2 122.01(14)
O3 C28 N 102.69(10)
O3 C28 C30 107.07(11)
N C28 C30 113.07(11)
O3 C28 C29 110.40(11)
N C28 C29 112.17(11)
C30 C28 C29 111.01(12)
C9 C10 C11 120.84(15)
C21 C20 C19 120.52(13)
C3 C2 C1 116.48(11)
C23 C24 C19 120.90(14)
C13 C14 C9 120.62(14)
C24 C23 C22 120.12(14)
C24 C19 C20 118.43(13)
C24 C19 C18 120.04(13)
C20 C19 C18 121.47(12)
C22 C21 C20 120.33(15)
C5 C4 C3 120.20(16)
C12 C13 C14 120.37(16)
C12 C11 C10 120.39(15)
C6 C7 C8 120.02(18)
C19 C18 C17 112.34(11)
C7 C6 C5 119.82(16)
C3 C8 C7 120.99(16)
O3 C25 C27 106.88(12)
O3 C25 C26 111.45(12)
C27 C25 C26 110.09(13)
O3 C25 C17 102.07(10)
C27 C25 C17 115.32(13)
C26 C25 C17 110.72(12)
C6 C5 C4 120.53(16)
C11 C12 C13 119.41(15)
C21 C22 C23 119.64(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C30 C28 1.526(2)
O1 C1 1.4241(17)
O3 C28 1.4338(17)
O3 C25 1.4472(17)
O2 C16 1.2414(17)
N C16 1.3477(17)
N C17 1.4704(17)
N C28 1.4992(16)
C16 C15 1.5273(17)
C15 C1 1.5496(18)
C17 C25 1.5475(18)
C17 C18 1.5488(19)
C1 C9 1.5371(18)
C1 C2 1.5493(18)
C9 C10 1.389(2)
C9 C14 1.397(2)
C3 C8 1.388(2)
C3 C4 1.404(2)
C3 C2 1.5104(19)
C28 C29 1.528(2)
C10 C11 1.396(2)
C20 C21 1.392(2)
C20 C19 1.397(2)
C24 C23 1.387(2)
C24 C19 1.3961(19)
C14 C13 1.395(2)
C23 C22 1.388(2)
C19 C18 1.512(2)
C26 C25 1.526(2)
C21 C22 1.385(2)
C4 C5 1.393(2)
C13 C12 1.385(3)
C11 C12 1.381(3)
C7 C6 1.378(3)
C7 C8 1.398(2)
C6 C5 1.383(3)
C25 C27 1.516(2)
