#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/48/1504878.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_1504878
loop_
_publ_author_name
'Duan, Haifeng'
'Sun, Xiaohua'
'Liao, Wenyan'
'Petersen, Jeffrey L.'
'Shi, Xiaodong'
_publ_section_title
;
 Proline as Lewis base catalyst: diastereoselective synthesis of
 isoxazoline-N-oxide through [3 + 2] cycloaddition.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4113
_journal_page_last               4116
_journal_paper_doi               10.1021/ol801656y
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C16 H23 N O2'
_chemical_formula_weight         261.35
_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                   6.4956(5)
_cell_length_b                   18.0854(16)
_cell_length_c                   24.885(2)
_cell_measurement_reflns_used    6959
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.25
_cell_volume                     2923.4(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0565
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19162
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3344
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0478
_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)+(0.0638P)²+0.5575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1444
_reflns_number_gt                2221
_reflns_number_total             3344
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801656y_si_003.cif
_cod_data_source_block           ms19ccd
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1504878
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 0.55834(16) 0.76695(8) 0.87857(6) 0.0671(4) Uani 1 1 d . . .
O2 O 0.35720(16) 0.72466(7) 0.81168(5) 0.0506(3) Uani 1 1 d . . .
N1 N 0.37719(18) 0.76099(7) 0.86303(5) 0.0449(3) Uani 1 1 d . . .
C1 C 0.1992(2) 0.78178(8) 0.88217(6) 0.0401(4) Uani 1 1 d . A .
C2 C 0.0330(2) 0.76367(9) 0.84240(6) 0.0412(4) Uani 1 1 d . . .
H2 H -0.0850 0.7414 0.8608 0.049 Uiso 1 1 calc R . .
C3 C 0.1415(2) 0.70554(9) 0.80736(6) 0.0426(4) Uani 1 1 d . B .
H3 H 0.0980 0.7124 0.7700 0.051 Uiso 1 1 calc R . .
C4 C 0.1743(2) 0.81949(9) 0.93333(7) 0.0428(4) Uani 1 1 d D . .
C5 C 0.3581(19) 0.8339(6) 0.9695(4) 0.049(2) Uani 0.539(11) 1 d PD A 1
H5A H 0.4368 0.7886 0.9731 0.059 Uiso 0.539(11) 1 calc PR A 1
H5B H 0.4461 0.8705 0.9526 0.059 Uiso 0.539(11) 1 calc PR A 1
C6 C 0.2994(7) 0.8606(5) 1.0241(2) 0.0721(18) Uani 0.539(11) 1 d P A 1
H6A H 0.4165 0.8856 1.0401 0.086 Uiso 0.539(11) 1 calc PR A 1
H6B H 0.2664 0.8184 1.0465 0.086 Uiso 0.539(11) 1 calc PR A 1
C7 C 0.1187(12) 0.9126(4) 1.0236(3) 0.0659(17) Uani 0.539(11) 1 d P A 1
H7A H 0.0961 0.9318 1.0596 0.079 Uiso 0.539(11) 1 calc PR A 1
H7B H 0.1480 0.9540 1.0001 0.079 Uiso 0.539(11) 1 calc PR A 1
C8 C -0.071(2) 0.8738(7) 1.0047(7) 0.070(3) Uani 0.539(11) 1 d P A 1
H8A H -0.1830 0.9088 1.0006 0.084 Uiso 0.539(11) 1 calc PR A 1
H8B H -0.1124 0.8366 1.0306 0.084 Uiso 0.539(11) 1 calc PR A 1
C9 C -0.0226(8) 0.8377(6) 0.9512(4) 0.053(3) Uani 0.539(11) 1 d PD A 1
H9A H -0.1326 0.8269 0.9286 0.063 Uiso 0.539(11) 1 calc PR A 1
C5' C 0.352(2) 0.8512(6) 0.9618(5) 0.046(2) Uani 0.461(11) 1 d PD A 2
H5C H 0.4387 0.8756 0.9355 0.056 Uiso 0.461(11) 1 calc PR A 2
H5D H 0.4307 0.8109 0.9771 0.056 Uiso 0.461(11) 1 calc PR A 2
C6' C 0.3052(9) 0.9051(5) 1.0055(3) 0.072(2) Uani 0.461(11) 1 d PD A 2
H6C H 0.2831 0.9536 0.9899 0.086 Uiso 0.461(11) 1 calc PR A 2
H6D H 0.4229 0.9084 1.0294 0.086 Uiso 0.461(11) 1 calc PR A 2
C7' C 0.1159(17) 0.8833(7) 1.0379(4) 0.081(3) Uani 0.461(11) 1 d PD A 2
H7C H 0.0824 0.9216 1.0638 0.097 Uiso 0.461(11) 1 calc PR A 2
H7D H 0.1412 0.8376 1.0572 0.097 Uiso 0.461(11) 1 calc PR A 2
C8' C -0.0620(19) 0.8731(10) 0.9978(7) 0.073(5) Uani 0.461(11) 1 d PD A 2
H8C H -0.1742 0.8484 1.0162 0.088 Uiso 0.461(11) 1 calc PR A 2
H8D H -0.1109 0.9217 0.9873 0.088 Uiso 0.461(11) 1 calc PR A 2
C9' C -0.0144(15) 0.8313(8) 0.9488(5) 0.066(4) Uani 0.461(11) 1 d PD A 2
H9B H -0.1220 0.8127 0.9282 0.079 Uiso 0.461(11) 1 calc PR A 2
C10 C -0.0355(3) 0.83132(10) 0.81085(8) 0.0604(5) Uani 1 1 d . . .
H10A H -0.0883 0.8679 0.8352 0.091 Uiso 1 1 calc R . .
H10B H -0.1413 0.8174 0.7859 0.091 Uiso 1 1 calc R . .
H10C H 0.0797 0.8514 0.7916 0.091 Uiso 1 1 calc R . .
C11 C 0.1011(2) 0.62670(9) 0.82321(6) 0.0426(4) Uani 1 1 d D . .
C12 C -0.1129(16) 0.5982(5) 0.8136(4) 0.0513(16) Uani 0.593(12) 1 d P B 1
H12A H -0.2089 0.6306 0.8319 0.062 Uiso 0.593(12) 1 calc PR B 1
H12B H -0.1417 0.6017 0.7754 0.062 Uiso 0.593(12) 1 calc PR B 1
C13 C -0.1537(15) 0.5230(5) 0.8307(4) 0.0718(19) Uani 0.593(12) 1 d P B 1
H13A H -0.2597 0.5022 0.8077 0.086 Uiso 0.593(12) 1 calc PR B 1
H13B H -0.2070 0.5240 0.8671 0.086 Uiso 0.593(12) 1 calc PR B 1
C14 C 0.0323(9) 0.4728(2) 0.8291(3) 0.0758(16) Uani 0.593(12) 1 d P B 1
H14A H -0.0033 0.4250 0.8442 0.091 Uiso 0.593(12) 1 calc PR B 1
H14B H 0.0747 0.4652 0.7922 0.091 Uiso 0.593(12) 1 calc PR B 1
C15 C 0.2019(12) 0.5049(5) 0.8596(5) 0.081(4) Uani 0.593(12) 1 d P B 1
H15A H 0.3250 0.4758 0.8534 0.098 Uiso 0.593(12) 1 calc PR B 1
H15B H 0.1697 0.5022 0.8976 0.098 Uiso 0.593(12) 1 calc PR B 1
C16 C 0.247(2) 0.5859(5) 0.8446(6) 0.054(2) Uani 0.593(12) 1 d PD B 1
H16A H 0.3763 0.6059 0.8508 0.065 Uiso 0.593(12) 1 calc PR B 1
C12' C -0.095(3) 0.5989(9) 0.7992(6) 0.067(4) Uani 0.407(12) 1 d PD B 2
H12C H -0.0945 0.6090 0.7609 0.080 Uiso 0.407(12) 1 calc PR B 2
H12D H -0.2097 0.6252 0.8150 0.080 Uiso 0.407(12) 1 calc PR B 2
C13' C -0.123(3) 0.5159(8) 0.8082(5) 0.083(4) Uani 0.407(12) 1 d PD B 2
H13C H -0.2698 0.5057 0.8095 0.099 Uiso 0.407(12) 1 calc PR B 2
H13D H -0.0680 0.4901 0.7772 0.099 Uiso 0.407(12) 1 calc PR B 2
C14' C -0.0247(14) 0.4839(4) 0.8584(5) 0.072(2) Uani 0.407(12) 1 d PD B 2
H14C H -0.0373 0.4305 0.8575 0.087 Uiso 0.407(12) 1 calc PR B 2
H14D H -0.0986 0.5017 0.8897 0.087 Uiso 0.407(12) 1 calc PR B 2
C15' C 0.207(2) 0.5048(9) 0.8640(8) 0.095(6) Uani 0.407(12) 1 d PD B 2
H15C H 0.2536 0.4956 0.9004 0.115 Uiso 0.407(12) 1 calc PR B 2
H15D H 0.2894 0.4756 0.8395 0.115 Uiso 0.407(12) 1 calc PR B 2
C16' C 0.225(3) 0.5831(9) 0.8511(8) 0.064(5) Uani 0.407(12) 1 d PD B 2
H16B H 0.3416 0.6061 0.8647 0.077 Uiso 0.407(12) 1 calc PR B 2
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
N1 O2 C3 105.18(10)
O1 N1 C1 134.38(14)
O1 N1 O2 113.59(12)
C1 N1 O2 112.00(12)
N1 C1 C4 123.60(13)
N1 C1 C2 109.48(13)
C4 C1 C2 126.87(13)
C1 C2 C10 112.05(14)
C1 C2 C3 101.16(11)
C10 C2 C3 113.07(14)
O2 C3 C11 112.12(12)
O2 C3 C2 103.79(12)
C11 C3 C2 114.84(13)
C9' C4 C9 4.5(10)
C9' C4 C1 116.1(6)
C9 C4 C1 119.5(4)
C9' C4 C5' 122.1(8)
C9 C4 C5' 118.3(7)
C1 C4 C5' 121.2(5)
C9' C4 C5 122.5(8)
C9 C4 C5 119.5(7)
C1 C4 C5 120.8(5)
C5' C4 C5 14.1(7)
C6 C5 C4 113.3(9)
C5 C6 C7 113.2(7)
C8 C7 C6 110.6(8)
C7 C8 C9 107.9(10)
C4 C9 C8 124.9(8)
C4 C5' C6' 116.7(9)
C5' C6' C7' 112.3(8)
C6' C7' C8' 107.0(10)
C9' C8' C7' 116.3(11)
C4 C9' C8' 121.9(10)
C16 C11 C16' 9.6(19)
C16 C11 C12' 125.9(8)
C16' C11 C12' 121.7(10)
C16 C11 C12 122.6(7)
C16' C11 C12 116.1(10)
C12' C11 C12 14.5(8)
C16 C11 C3 121.0(6)
C16' C11 C3 126.7(9)
C12' C11 C3 111.3(6)
C12 C11 C3 116.5(3)
C13 C12 C11 116.4(7)
C12 C13 C14 114.3(7)
C15 C14 C13 110.6(7)
C14 C15 C16 113.4(7)
C11 C16 C15 119.8(10)
C11 C12' C13' 112.1(12)
C14' C13' C12' 116.3(10)
C13' C14' C15' 112.9(12)
C16' C15' C14' 107.1(12)
C11 C16' C15' 130.3(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.2433(15)
O2 N1 1.4426(17)
O2 C3 1.4470(18)
N1 C1 1.3055(18)
C1 C4 1.453(2)
C1 C2 1.501(2)
C2 C10 1.520(2)
C2 C3 1.537(2)
C3 C11 1.502(2)
C4 C9' 1.302(10)
C4 C9 1.394(7)
C4 C5' 1.468(12)
C4 C5 1.517(11)
C5 C6 1.492(13)
C6 C7 1.504(11)
C7 C8 1.495(13)
C8 C9 1.516(18)
C5' C6' 1.492(13)
C6' C7' 1.523(12)
C7' C8' 1.539(14)
C8' C9' 1.47(2)
C11 C16 1.312(8)
C11 C16' 1.322(12)
C11 C12' 1.492(19)
C11 C12 1.502(12)
C12 C13 1.450(11)
C13 C14 1.512(11)
C14 C15 1.458(10)
C15 C16 1.539(15)
C12' C13' 1.528(16)
C13' C14' 1.519(14)
C14' C15' 1.555(14)
C15' C16' 1.46(2)
