#------------------------------------------------------------------------------
#$Date: 2016-03-26 12:42:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180214 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/00/7110055.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_7110055
loop_
_publ_author_name
'Juan Mancebo-Aracil'
'Carmen Najera'
'Jose M. Sansano'
_publ_section_title
;
 Multicomponent synthesis of unnatural pyrrolizidines using 1,3-dipolar
 cycloaddition of proline esters
;
_journal_name_full               Chem.Commun.
_journal_page_first              11218
_journal_paper_doi               10.1039/c3cc47184e
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H23 N O5'
_chemical_formula_sum            'C19 H23 N O5'
_chemical_formula_weight         345.38
_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                 94.567(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.1442(19)
_cell_length_b                   5.9143(10)
_cell_length_c                   13.609(2)
_cell_measurement_reflns_used    903
_cell_measurement_temperature    298(1)
_cell_measurement_theta_max      21.18
_cell_measurement_theta_min      2.25
_cell_volume                     894.1(3)
_computing_cell_refinement       'Bruker SMART V5.625'
_computing_data_collection       'Bruker SMART V5.625'
_computing_data_reduction        'Bruker SAINT V6.28A'
_computing_molecular_graphics    'SHELXTL  Rel. 6.12/V (Siemens, 1996)'
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(1)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7694
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9972
_exptl_absorpt_correction_T_min  0.9276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker/Siemens SADABS V2.03'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3131
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0622P)²+0.0067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1415
_reflns_number_gt                1784
_reflns_number_total             3131
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3cc47184e.txt
_cod_data_source_block           x
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7110055
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
_atom_site_refinement_flags
N1 N 0.2961(3) 0.2084(5) 0.1332(2) 0.0616(8) Uani 1 1 d .
C1 C 0.4009(4) 0.3603(7) 0.1399(3) 0.0713(11) Uani 1 1 d .
H1A H 0.4718 0.2810 0.1211 0.086 Uiso 1 1 calc R
H1B H 0.4168 0.4154 0.2068 0.086 Uiso 1 1 calc R
C2 C 0.3707(3) 0.5555(7) 0.0700(3) 0.0681(10) Uani 1 1 d .
H2 H 0.3932 0.5174 0.0039 0.082 Uiso 1 1 calc R
O1 O 0.4319(3) 0.7564(5) 0.1043(3) 0.0946(10) Uani 1 1 d .
H1 H 0.3964 0.8673 0.0803 0.142 Uiso 1 1 calc R
C3 C 0.2353(3) 0.5687(7) 0.0700(3) 0.0744(11) Uani 1 1 d .
H3A H 0.2004 0.6419 0.0106 0.089 Uiso 1 1 calc R
H3B H 0.2119 0.6513 0.1270 0.089 Uiso 1 1 calc R
C4 C 0.1958(3) 0.3232(6) 0.0738(2) 0.0620(10) Uani 1 1 d .
C5 C 0.0830(3) 0.2767(7) 0.1267(3) 0.0731(11) Uani 1 1 d .
H5A H 0.0627 0.4055 0.1663 0.088 Uiso 1 1 calc R
H5B H 0.0152 0.2416 0.0801 0.088 Uiso 1 1 calc R
C6 C 0.1176(3) 0.0746(7) 0.1911(3) 0.0663(10) Uani 1 1 d .
H6 H 0.1140 -0.0609 0.1495 0.080 Uiso 1 1 calc R
C7 C 0.2512(3) 0.1221(6) 0.2250(2) 0.0598(10) Uani 1 1 d .
H7 H 0.2913 -0.0217 0.2420 0.072 Uiso 1 1 calc R
C8 C 0.1794(4) 0.2350(8) -0.0318(3) 0.0805(12) Uani 1 1 d .
O2 O 0.1023(5) 0.2978(10) -0.0883(3) 0.204(3) Uani 1 1 d .
O3 O 0.2541(3) 0.0828(6) -0.05329(19) 0.0911(9) Uani 1 1 d .
C9 C 0.2422(5) 0.0071(11) -0.1563(3) 0.119(2) Uani 1 1 d .
H9A H 0.1648 0.0508 -0.1863 0.179 Uiso 1 1 calc R
H9B H 0.2499 -0.1545 -0.1586 0.179 Uiso 1 1 calc R
H9C H 0.3042 0.0754 -0.1914 0.179 Uiso 1 1 calc R
C10 C 0.0398(4) 0.0370(8) 0.2738(3) 0.0753(12) Uani 1 1 d .
O4 O -0.0262(3) 0.1731(6) 0.3061(3) 0.1117(12) Uani 1 1 d .
O5 O 0.0528(2) -0.1720(5) 0.3090(2) 0.0825(8) Uani 1 1 d .
C11 C -0.0213(4) -0.2358(9) 0.3864(3) 0.1111(17) Uani 1 1 d .
H11A H 0.0048 -0.1562 0.4458 0.167 Uiso 1 1 calc R
H11B H -0.0146 -0.3956 0.3977 0.167 Uiso 1 1 calc R
H11C H -0.1037 -0.1980 0.3673 0.167 Uiso 1 1 calc R
C12 C 0.2635(3) 0.2749(7) 0.3130(3) 0.0621(10) Uani 1 1 d .
H12 H 0.2274 0.4167 0.3084 0.074 Uiso 1 1 calc R
C13 C 0.3235(3) 0.2169(7) 0.3973(3) 0.0622(10) Uani 1 1 d .
H13 H 0.3619 0.0772 0.3979 0.075 Uiso 1 1 calc R
C14 C 0.3369(3) 0.3453(7) 0.4894(3) 0.0608(10) Uani 1 1 d .
C15 C 0.4041(3) 0.2528(8) 0.5699(3) 0.0772(12) Uani 1 1 d .
H15 H 0.4417 0.1136 0.5638 0.093 Uiso 1 1 calc R
C16 C 0.4157(4) 0.3652(10) 0.6587(3) 0.0933(15) Uani 1 1 d .
H16 H 0.4608 0.3015 0.7122 0.112 Uiso 1 1 calc R
C17 C 0.3617(5) 0.5686(12) 0.6687(4) 0.1038(17) Uani 1 1 d .
H17 H 0.3695 0.6425 0.7292 0.125 Uiso 1 1 calc R
C18 C 0.2952(4) 0.6669(9) 0.5901(4) 0.0964(15) Uani 1 1 d .
H18 H 0.2586 0.8067 0.5970 0.116 Uiso 1 1 calc R
C19 C 0.2841(4) 0.5523(8) 0.5002(3) 0.0747(11) Uani 1 1 d .
H19 H 0.2401 0.6176 0.4466 0.090 Uiso 1 1 calc R
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
C1 N1 C7 118.7(3)
C1 N1 C4 108.2(3)
C7 N1 C4 109.1(3)
N1 C1 C2 106.9(3)
N1 C1 H1A 110.3
C2 C1 H1A 110.3
N1 C1 H1B 110.3
C2 C1 H1B 110.3
H1A C1 H1B 108.6
O1 C2 C3 114.1(3)
O1 C2 C1 110.6(3)
C3 C2 C1 102.2(3)
O1 C2 H2 109.9
C3 C2 H2 109.9
C1 C2 H2 109.9
C2 O1 H1 109.5
C2 C3 C4 104.1(3)
C2 C3 H3A 110.9
C4 C3 H3A 110.9
C2 C3 H3B 110.9
C4 C3 H3B 110.9
H3A C3 H3B 109.0
N1 C4 C3 104.3(3)
N1 C4 C5 105.8(3)
C3 C4 C5 116.2(3)
N1 C4 C8 112.5(3)
C3 C4 C8 107.9(3)
C5 C4 C8 110.0(3)
C6 C5 C4 103.6(3)
C6 C5 H5A 111.0
C4 C5 H5A 111.0
C6 C5 H5B 111.0
C4 C5 H5B 111.0
H5A C5 H5B 109.0
C10 C6 C5 114.7(3)
C10 C6 C7 113.9(3)
C5 C6 C7 102.9(3)
C10 C6 H6 108.3
C5 C6 H6 108.3
C7 C6 H6 108.3
N1 C7 C12 117.0(3)
N1 C7 C6 101.2(3)
C12 C7 C6 111.8(3)
N1 C7 H7 108.8
C12 C7 H7 108.8
C6 C7 H7 108.8
O2 C8 O3 122.2(4)
O2 C8 C4 122.5(4)
O3 C8 C4 115.2(4)
C8 O3 C9 115.1(4)
O3 C9 H9A 109.5
O3 C9 H9B 109.5
H9A C9 H9B 109.5
O3 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O4 C10 O5 123.0(4)
O4 C10 C6 126.0(5)
O5 C10 C6 110.9(4)
C10 O5 C11 117.0(3)
O5 C11 H11A 109.5
O5 C11 H11B 109.5
H11A C11 H11B 109.5
O5 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C13 C12 C7 122.9(4)
C13 C12 H12 118.5
C7 C12 H12 118.5
C12 C13 C14 128.0(4)
C12 C13 H13 116.0
C14 C13 H13 116.0
C19 C14 C15 118.4(4)
C19 C14 C13 122.7(4)
C15 C14 C13 118.9(4)
C16 C15 C14 120.6(4)
C16 C15 H15 119.7
C14 C15 H15 119.7
C17 C16 C15 120.3(5)
C17 C16 H16 119.9
C15 C16 H16 119.9
C16 C17 C18 120.8(5)
C16 C17 H17 119.6
C18 C17 H17 119.6
C17 C18 C19 118.6(5)
C17 C18 H18 120.7
C19 C18 H18 120.7
C14 C19 C18 121.3(4)
C14 C19 H19 119.4
C18 C19 H19 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.471(5)
N1 C7 1.473(4)
N1 C4 1.490(4)
C1 C2 1.516(5)
C1 H1A 0.9700
C1 H1B 0.9700
C2 O1 1.429(5)
C2 C3 1.511(5)
C2 H2 0.9800
O1 H1 0.8200
C3 C4 1.519(6)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.522(5)
C4 C8 1.525(5)
C5 C6 1.513(5)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C10 1.490(5)
C6 C7 1.549(5)
C6 H6 0.9800
C7 C12 1.499(5)
C7 H7 0.9800
C8 O2 1.167(5)
C8 O3 1.275(5)
O3 C9 1.468(5)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 O4 1.198(5)
C10 O5 1.329(5)
O5 C11 1.440(5)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 C13 1.326(4)
C12 H12 0.9300
C13 C14 1.463(5)
C13 H13 0.9300
C14 C19 1.371(5)
C14 C15 1.390(5)
C15 C16 1.376(6)
C15 H15 0.9300
C16 C17 1.357(7)
C16 H16 0.9300
C17 C18 1.380(7)
C17 H17 0.9300
C18 C19 1.396(6)
C18 H18 0.9300
C19 H19 0.9300
