#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:16:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178428 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/49/4024943.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_4024943
loop_
_publ_author_name
'Chan Woo Huh'
'Gagandeep K. Somal'
'Christopher E. Katz'
'Huaxing Pei'
'Yibin Zeng'
'Justin T. Douglas'
'Jeffrey Aubé'
_publ_contact_author
; 
   Professor Jeffrey Aubé 
   Department of Medicinal Chemistry -- University of Kansas 
   Malott Hall 
   1251 Wescoe Hall Dr, Rm 4070 
   Lawrence, KS  66045-7582  USA 
;
_publ_contact_author_email       jaube@ku.edu
_publ_contact_author_fax         1(785)8645326
_publ_contact_author_phone       1(785)8644496
_publ_section_title
;
One-Pot Synthesis of Lactams Using Domino Reactions: Combination of Schmidt
Reaction with Sakurai and Aldol Reactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7618
_journal_page_last               7626
_journal_paper_doi               10.1021/jo901843w
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C14 H23 N O2'
_chemical_formula_weight         237.33
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.5311(5)
_cell_length_b                   15.1592(9)
_cell_length_c                   18.9260(11)
_cell_measurement_reflns_used    9721
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.34
_cell_measurement_theta_min      2.69
_cell_volume                     2734.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            30778
_diffrn_reflns_theta_full        30.49
_diffrn_reflns_theta_max         30.49
_diffrn_reflns_theta_min         2.69
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Rectangular parallelepiped'
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0781P)²+0.2044P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1284
_reflns_number_gt                3666
_reflns_number_total             4159
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901843w_si_002_4.cif
_cod_data_source_block           Cmpd_26a_(k16g)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4024943
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.27030(8) 0.42293(4) 0.38528(4) 0.02163(18) Uani 1 1 d . . .
O2 O 0.22764(8) 0.09376(5) 0.42553(4) 0.01806(17) Uani 1 1 d . . .
H2O H 0.2272(16) 0.0394(11) 0.4090(8) 0.035(4) Uiso 1 1 d . . .
N N 0.31196(8) 0.28231(5) 0.41696(4) 0.01394(17) Uani 1 1 d . . .
C1 C 0.31924(10) 0.36970(6) 0.42889(5) 0.01548(19) Uani 1 1 d . . .
C2 C 0.38591(10) 0.40146(6) 0.49645(5) 0.0180(2) Uani 1 1 d . . .
H2A H 0.4858(15) 0.3844(9) 0.4969(7) 0.023(3) Uiso 1 1 d . . .
H2B H 0.3798(14) 0.4658(9) 0.4944(6) 0.024(3) Uiso 1 1 d . . .
C3 C 0.31574(11) 0.36664(7) 0.56355(5) 0.0196(2) Uani 1 1 d . . .
H3A H 0.3398(16) 0.4063(9) 0.6024(8) 0.034(4) Uiso 1 1 d . . .
H3B H 0.2118(14) 0.3684(9) 0.5580(8) 0.025(3) Uiso 1 1 d . . .
C4 C 0.36432(11) 0.27462(7) 0.58458(5) 0.0187(2) Uani 1 1 d . . .
H4A H 0.4678(14) 0.2743(9) 0.5897(7) 0.024(3) Uiso 1 1 d . . .
H4B H 0.3272(14) 0.2586(9) 0.6333(8) 0.027(3) Uiso 1 1 d . . .
C5 C 0.32524(10) 0.19894(6) 0.53481(5) 0.01437(18) Uani 1 1 d . . .
H5 H 0.2218(13) 0.1933(8) 0.5331(7) 0.017(3) Uiso 1 1 d . . .
C6 C 0.38110(9) 0.21160(6) 0.45943(5) 0.01299(18) Uani 1 1 d . . .
H6 H 0.4814(13) 0.2245(8) 0.4629(7) 0.018(3) Uiso 1 1 d . . .
C7 C 0.36134(10) 0.13072(6) 0.41103(5) 0.01417(18) Uani 1 1 d . . .
H7 H 0.4379(13) 0.0880(8) 0.4196(6) 0.016(3) Uiso 1 1 d . . .
C8 C 0.36571(10) 0.16973(6) 0.33591(5) 0.01525(19) Uani 1 1 d . . .
C9 C 0.27153(10) 0.25034(6) 0.34610(5) 0.01511(19) Uani 1 1 d . . .
H9A H 0.1701(13) 0.2348(9) 0.3449(7) 0.019(3) Uiso 1 1 d . . .
H9B H 0.2865(14) 0.2977(9) 0.3117(8) 0.022(3) Uiso 1 1 d . . .
C10 C 0.38548(12) 0.11239(6) 0.56577(5) 0.0191(2) Uani 1 1 d . . .
H10A H 0.4873(16) 0.1163(9) 0.5676(8) 0.031(4) Uiso 1 1 d . . .
H10B H 0.3619(14) 0.0633(9) 0.5342(8) 0.026(3) Uiso 1 1 d . . .
C11 C 0.33146(13) 0.09140(7) 0.63839(6) 0.0249(2) Uani 1 1 d . . .
H11 H 0.2336(15) 0.0837(9) 0.6421(8) 0.027(4) Uiso 1 1 d . . .
C12 C 0.41143(17) 0.08286(8) 0.69537(6) 0.0331(3) Uani 1 1 d . . .
H12A H 0.3711(16) 0.0678(10) 0.7428(10) 0.044(4) Uiso 1 1 d . . .
H12B H 0.516(2) 0.0909(11) 0.6905(11) 0.054(5) Uiso 1 1 d . . .
C13 C 0.51477(11) 0.19862(8) 0.31678(6) 0.0242(2) Uani 1 1 d . . .
H13A H 0.5177(17) 0.2233(11) 0.2670(9) 0.042(4) Uiso 1 1 d . . .
H13B H 0.5529(15) 0.2456(9) 0.3495(8) 0.031(4) Uiso 1 1 d . . .
H13C H 0.5790(15) 0.1478(10) 0.3191(7) 0.032(4) Uiso 1 1 d . . .
C14 C 0.31059(12) 0.10604(7) 0.28020(5) 0.0218(2) Uani 1 1 d . . .
H14A H 0.2113(16) 0.0869(9) 0.2892(8) 0.027(4) Uiso 1 1 d . . .
H14B H 0.3124(15) 0.1321(11) 0.2343(8) 0.036(4) Uiso 1 1 d . . .
H14C H 0.3687(16) 0.0529(11) 0.2770(8) 0.040(4) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 H2O 107.7(10) . . ?
C1 N C9 119.27(8) . . ?
C1 N C6 126.41(8) . . ?
C9 N C6 111.62(7) . . ?
O1 C1 N 120.49(9) . . ?
O1 C1 C2 120.90(9) . . ?
N C1 C2 118.60(8) . . ?
C1 C2 C3 114.20(8) . . ?
C1 C2 H2A 109.3(8) . . ?
C3 C2 H2A 108.9(8) . . ?
C1 C2 H2B 105.1(7) . . ?
C3 C2 H2B 110.6(7) . . ?
H2A C2 H2B 108.6(11) . . ?
C4 C3 C2 113.60(9) . . ?
C4 C3 H3A 107.2(8) . . ?
C2 C3 H3A 108.0(9) . . ?
C4 C3 H3B 110.7(8) . . ?
C2 C3 H3B 109.8(8) . . ?
H3A C3 H3B 107.2(12) . . ?
C3 C4 C5 116.86(8) . . ?
C3 C4 H4A 109.4(8) . . ?
C5 C4 H4A 107.4(8) . . ?
C3 C4 H4B 110.4(8) . . ?
C5 C4 H4B 107.2(8) . . ?
H4A C4 H4B 104.8(11) . . ?
C4 C5 C6 113.20(8) . . ?
C4 C5 C10 108.19(8) . . ?
C6 C5 C10 109.23(7) . . ?
C4 C5 H5 109.1(7) . . ?
C6 C5 H5 109.0(7) . . ?
C10 C5 H5 108.0(7) . . ?
N C6 C5 115.92(7) . . ?
N C6 C7 101.37(7) . . ?
C5 C6 C7 114.23(7) . . ?
N C6 H6 108.9(7) . . ?
C5 C6 H6 107.5(7) . . ?
C7 C6 H6 108.5(7) . . ?
O2 C7 C8 110.75(8) . . ?
O2 C7 C6 107.98(7) . . ?
C8 C7 C6 103.87(7) . . ?
O2 C7 H7 111.9(7) . . ?
C8 C7 H7 112.5(7) . . ?
C6 C7 H7 109.4(7) . . ?
C14 C8 C9 113.06(8) . . ?
C14 C8 C13 109.75(8) . . ?
C9 C8 C13 110.27(8) . . ?
C14 C8 C7 112.72(8) . . ?
C9 C8 C7 100.05(7) . . ?
C13 C8 C7 110.69(8) . . ?
N C9 C8 102.93(7) . . ?
N C9 H9A 110.6(7) . . ?
C8 C9 H9A 112.2(8) . . ?
N C9 H9B 108.9(8) . . ?
C8 C9 H9B 114.6(8) . . ?
H9A C9 H9B 107.5(11) . . ?
C11 C10 C5 113.51(8) . . ?
C11 C10 H10A 108.8(9) . . ?
C5 C10 H10A 109.4(8) . . ?
C11 C10 H10B 108.5(8) . . ?
C5 C10 H10B 109.2(8) . . ?
H10A C10 H10B 107.3(11) . . ?
C12 C11 C10 124.58(12) . . ?
C12 C11 H11 119.7(9) . . ?
C10 C11 H11 115.7(9) . . ?
C11 C12 H12A 122.0(9) . . ?
C11 C12 H12B 118.8(11) . . ?
H12A C12 H12B 119.3(15) . . ?
C8 C13 H13A 110.5(9) . . ?
C8 C13 H13B 113.0(8) . . ?
H13A C13 H13B 107.4(12) . . ?
C8 C13 H13C 110.0(8) . . ?
H13A C13 H13C 108.2(12) . . ?
H13B C13 H13C 107.4(12) . . ?
C8 C14 H14A 113.0(8) . . ?
C8 C14 H14B 111.2(9) . . ?
H14A C14 H14B 106.9(12) . . ?
C8 C14 H14C 111.7(9) . . ?
H14A C14 H14C 107.8(12) . . ?
H14B C14 H14C 105.9(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2449(12) . ?
O2 C7 1.4188(12) . ?
O2 H2O 0.882(16) . ?
N C1 1.3457(12) . ?
N C9 1.4771(12) . ?
N C6 1.4931(11) . ?
C1 C2 1.5067(13) . ?
C2 C3 1.5292(14) . ?
C2 H2A 0.986(14) . ?
C2 H2B 0.977(14) . ?
C3 C4 1.5227(14) . ?
C3 H3A 0.977(15) . ?
C3 H3B 0.996(14) . ?
C4 C5 1.5304(13) . ?
C4 H4A 0.991(13) . ?
C4 H4B 1.018(15) . ?
C5 C6 1.5347(13) . ?
C5 C10 1.5474(13) . ?
C5 H5 0.990(13) . ?
C6 C7 1.5421(12) . ?
C6 H6 0.978(13) . ?
C7 C8 1.5405(13) . ?
C7 H7 0.989(12) . ?
C8 C14 1.5231(14) . ?
C8 C9 1.5284(13) . ?
C8 C13 1.5301(14) . ?
C9 H9A 0.995(12) . ?
C9 H9B 0.980(14) . ?
C10 C11 1.5018(14) . ?
C10 H10A 0.973(15) . ?
C10 H10B 0.981(14) . ?
C11 C12 1.3269(18) . ?
C11 H11 0.943(14) . ?
C12 H12A 1.003(17) . ?
C12 H12B 1.013(19) . ?
C13 H13A 1.013(17) . ?
C13 H13B 1.011(15) . ?
C13 H13C 0.984(15) . ?
C14 H14A 1.005(15) . ?
C14 H14B 0.955(16) . ?
C14 H14C 0.979(16) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O O1 0.882(16) 1.822(17) 2.6995(10) 173.5(15) 8_655
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N C1 O1 12.07(14) . . . . ?
C6 N C1 O1 171.80(9) . . . . ?
C9 N C1 C2 -168.77(8) . . . . ?
C6 N C1 C2 -9.03(14) . . . . ?
O1 C1 C2 C3 120.73(10) . . . . ?
N C1 C2 C3 -58.43(12) . . . . ?
C1 C2 C3 C4 82.66(11) . . . . ?
C2 C3 C4 C5 -66.44(12) . . . . ?
C3 C4 C5 C6 58.36(12) . . . . ?
C3 C4 C5 C10 179.57(9) . . . . ?
C1 N C6 C5 67.72(12) . . . . ?
C9 N C6 C5 -131.25(8) . . . . ?
C1 N C6 C7 -168.02(9) . . . . ?
C9 N C6 C7 -6.99(9) . . . . ?
C4 C5 C6 N -70.82(10) . . . . ?
C10 C5 C6 N 168.56(8) . . . . ?
C4 C5 C6 C7 171.86(8) . . . . ?
C10 C5 C6 C7 51.24(10) . . . . ?
N C6 C7 O2 -85.71(8) . . . . ?
C5 C6 C7 O2 39.69(10) . . . . ?
N C6 C7 C8 31.93(8) . . . . ?
C5 C6 C7 C8 157.33(7) . . . . ?
O2 C7 C8 C14 -49.25(10) . . . . ?
C6 C7 C8 C14 -164.95(8) . . . . ?
O2 C7 C8 C9 71.11(9) . . . . ?
C6 C7 C8 C9 -44.59(9) . . . . ?
O2 C7 C8 C13 -172.59(8) . . . . ?
C6 C7 C8 C13 71.70(9) . . . . ?
C1 N C9 C8 141.85(8) . . . . ?
C6 N C9 C8 -20.70(9) . . . . ?
C14 C8 C9 N 159.29(8) . . . . ?
C13 C8 C9 N -77.44(9) . . . . ?
C7 C8 C9 N 39.17(9) . . . . ?
C4 C5 C10 C11 59.23(11) . . . . ?
C6 C5 C10 C11 -177.14(9) . . . . ?
C5 C10 C11 C12 -119.98(12) . . . . ?
