#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:50:45 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180237 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/23/7112359.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_7112359
loop_
_publ_author_name
'Jean, Alexandre'
'Blanchet, Jérôme'
'Rouden, Jacques'
'Maddaluno, Jacques'
'De Paolis, Michaël'
_publ_section_title
;
 Stereoselective access to heteroarylmethylene-substituted pyrrolidines:
 fully organocatalytic Mannich-hydroamination reactions.
;
_journal_issue                   16
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1651
_journal_page_last               1653
_journal_paper_doi               10.1039/c2cc38954a
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H28 N2 O5'
_chemical_formula_sum            'C24 H28 N2 O5'
_chemical_formula_weight         424.48
_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                 94.8530(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.7414(2)
_cell_length_b                   8.5308(2)
_cell_length_c                   20.2800(4)
_cell_measurement_reflns_used    7807
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      2.59
_cell_volume                     1162.11(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17720
_diffrn_reflns_theta_full        30.92
_diffrn_reflns_theta_max         30.92
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         7233
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0462
_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)+(0.0739P)²+0.1154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1335
_reflns_number_gt                6118
_reflns_number_total             7233
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7108857
_cod_data_source_file            c2cc38954a.txt
_cod_data_source_block           jean1_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7112359
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 0.62768(17) 0.32971(15) 0.29490(6) 0.0378(3) Uani 1 1 d .
N2 N 1.04031(18) 0.71248(17) 0.26958(7) 0.0427(3) Uani 1 1 d .
O5 O 0.75228(19) -0.12487(15) 0.49124(6) 0.0523(3) Uani 1 1 d .
O4 O -0.1390(2) 0.4725(3) 0.06036(7) 0.0920(6) Uani 1 1 d .
O2 O 0.6848(2) 0.18222(18) 0.17827(7) 0.0613(3) Uani 1 1 d .
O1 O 0.3590(3) 0.1218(2) 0.16358(9) 0.0819(5) Uani 1 1 d .
O3 O 0.1429(3) 0.5232(6) 0.02027(9) 0.1681(19) Uani 1 1 d .
C4 C 0.75471(18) 0.45315(16) 0.28548(6) 0.0334(3) Uani 1 1 d .
C10 C 1.06342(19) 0.60893(17) 0.31977(7) 0.0361(3) Uani 1 1 d .
C9 C 0.92277(19) 0.48143(18) 0.32523(7) 0.0367(3) Uani 1 1 d .
H9 H 0.9513 0.4114 0.3599 0.044 Uiso 1 1 calc R
C18 C 0.7332(2) -0.01705(18) 0.44106(7) 0.0370(3) Uani 1 1 d .
C2 C 0.45373(18) 0.4839(2) 0.21423(7) 0.0381(3) Uani 1 1 d .
H2 H 0.3726 0.5477 0.2418 0.046 Uiso 1 1 calc R
C15 C 0.66548(19) 0.21204(17) 0.34414(6) 0.0338(3) Uani 1 1 d .
C6 C 0.3663(2) 0.5010(2) 0.14281(7) 0.0457(4) Uani 1 1 d .
H6A H 0.3914 0.6064 0.1276 0.055 Uiso 1 1 calc R
H6B H 0.4331 0.4285 0.1152 0.055 Uiso 1 1 calc R
C20 C 0.8098(2) 0.09941(19) 0.33874(7) 0.0407(3) Uani 1 1 d .
H20 H 0.8848 0.1003 0.3023 0.049 Uiso 1 1 calc R
C1 C 0.4635(2) 0.3164(2) 0.24370(7) 0.0409(3) Uani 1 1 d .
H1 H 0.3400 0.2940 0.2642 0.049 Uiso 1 1 calc R
C19 C 0.8451(2) -0.0157(2) 0.38697(7) 0.0406(3) Uani 1 1 d .
H19 H 0.9431 -0.0910 0.3828 0.049 Uiso 1 1 calc R
C3 C 0.6693(2) 0.54181(19) 0.22592(7) 0.0404(3) Uani 1 1 d .
H3A H 0.7428 0.5195 0.1879 0.049 Uiso 1 1 calc R
H3B H 0.6731 0.6538 0.2342 0.049 Uiso 1 1 calc R
C16 C 0.5556(2) 0.2107(2) 0.39930(7) 0.0427(3) Uani 1 1 d .
H16 H 0.4596 0.2873 0.4040 0.051 Uiso 1 1 calc R
C11 C 1.2261(2) 0.6190(2) 0.36783(8) 0.0460(3) Uani 1 1 d .
H11 H 1.2402 0.5469 0.4023 0.055 Uiso 1 1 calc R
C7 C 0.1440(2) 0.4695(3) 0.13457(8) 0.0532(4) Uani 1 1 d .
H7A H 0.1197 0.3625 0.1480 0.064 Uiso 1 1 calc R
H7B H 0.0781 0.5387 0.1638 0.064 Uiso 1 1 calc R
C17 C 0.5885(2) 0.0960(2) 0.44715(7) 0.0449(3) Uani 1 1 d .
H17 H 0.5132 0.0947 0.4835 0.054 Uiso 1 1 calc R
C5 C 0.4946(3) 0.1931(2) 0.19130(8) 0.0515(4) Uani 1 1 d .
C13 C 1.3403(3) 0.8418(3) 0.31193(11) 0.0638(5) Uani 1 1 d .
H13 H 1.4315 0.9223 0.3078 0.077 Uiso 1 1 calc R
C14 C 1.1784(3) 0.8250(2) 0.26690(10) 0.0524(4) Uani 1 1 d .
H14 H 1.1632 0.8963 0.2322 0.063 Uiso 1 1 calc R
C12 C 1.3646(3) 0.7368(2) 0.36336(11) 0.0616(5) Uani 1 1 d .
H12 H 1.4730 0.7450 0.3947 0.074 Uiso 1 1 calc R
C8 C 0.0546(3) 0.4927(4) 0.06542(9) 0.0678(6) Uani 1 1 d .
C24 C 0.9041(4) -0.2385(3) 0.48996(12) 0.0706(6) Uani 1 1 d .
H24A H 0.8794 -0.3032 0.4514 0.106 Uiso 1 1 calc R
H24B H 0.9058 -0.3025 0.5289 0.106 Uiso 1 1 calc R
H24C H 1.0304 -0.1872 0.4887 0.106 Uiso 1 1 calc R
C21 C 0.7301(5) 0.0866(3) 0.12163(12) 0.0793(7) Uani 1 1 d .
H21A H 0.8582 0.1180 0.1075 0.095 Uiso 1 1 calc R
H21B H 0.6302 0.1053 0.0852 0.095 Uiso 1 1 calc R
C23 C -0.2447(4) 0.4908(8) -0.00430(15) 0.1398(19) Uani 1 1 d .
H23A H -0.2251 0.5952 -0.0202 0.210 Uiso 1 1 calc R
H23B H -0.3842 0.4729 -0.0012 0.210 Uiso 1 1 calc R
H23C H -0.1949 0.4165 -0.0344 0.210 Uiso 1 1 calc R
C22 C 0.7353(7) -0.0815(4) 0.13743(16) 0.1072(11) Uani 1 1 d .
H22A H 0.8261 -0.0994 0.1757 0.161 Uiso 1 1 calc R
H22B H 0.7785 -0.1391 0.1006 0.161 Uiso 1 1 calc R
H22C H 0.6045 -0.1158 0.1463 0.161 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
C4 N1 C15 123.96(11)
C4 N1 C1 113.81(11)
C15 N1 C1 121.67(11)
C14 N2 C10 117.63(13)
C18 O5 C24 118.04(13)
C8 O4 C23 117.8(2)
C5 O2 C21 117.56(18)
C9 C4 N1 123.40(12)
C9 C4 C3 129.38(12)
N1 C4 C3 107.22(11)
N2 C10 C11 121.14(13)
N2 C10 C9 120.93(12)
C11 C10 C9 117.92(13)
C4 C9 C10 127.29(13)
C4 C9 H9 116.4
C10 C9 H9 116.4
O5 C18 C19 124.88(14)
O5 C18 C17 115.07(12)
C19 C18 C17 120.04(13)
C6 C2 C3 113.65(11)
C6 C2 C1 117.10(14)
C3 C2 C1 103.24(11)
C6 C2 H2 107.5
C3 C2 H2 107.4
C1 C2 H2 107.5
C20 C15 C16 119.00(13)
C20 C15 N1 121.44(12)
C16 C15 N1 119.56(13)
C7 C6 C2 112.75(12)
C7 C6 H6A 109.0
C2 C6 H6A 109.0
C7 C6 H6B 109.0
C2 C6 H6B 109.0
H6A C6 H6B 107.8
C15 C20 C19 121.06(12)
C15 C20 H20 119.5
C19 C20 H20 119.5
N1 C1 C5 114.20(13)
N1 C1 C2 102.00(11)
C5 C1 C2 111.86(12)
N1 C1 H1 109.5
C5 C1 H1 109.5
C2 C1 H1 109.5
C18 C19 C20 119.39(14)
C18 C19 H19 120.3
C20 C19 H19 120.3
C4 C3 C2 104.84(11)
C4 C3 H3A 110.8
C2 C3 H3A 110.8
C4 C3 H3B 110.8
C2 C3 H3B 110.8
H3A C3 H3B 108.9
C17 C16 C15 120.32(14)
C17 C16 H16 119.8
C15 C16 H16 119.8
C12 C11 C10 119.40(16)
C12 C11 H11 120.3
C10 C11 H11 120.3
C8 C7 C6 113.36(14)
C8 C7 H7A 108.9
C6 C7 H7A 108.9
C8 C7 H7B 108.9
C6 C7 H7B 108.9
H7A C7 H7B 107.7
C16 C17 C18 120.17(13)
C16 C17 H17 119.9
C18 C17 H17 119.9
O1 C5 O2 125.4(2)
O1 C5 C1 122.24(19)
O2 C5 C1 112.21(13)
C14 C13 C12 118.33(16)
C14 C13 H13 120.8
C12 C13 H13 120.8
N2 C14 C13 124.37(17)
N2 C14 H14 117.8
C13 C14 H14 117.8
C13 C12 C11 119.13(16)
C13 C12 H12 120.4
C11 C12 H12 120.4
O3 C8 O4 122.67(18)
O3 C8 C7 125.24(18)
O4 C8 C7 112.09(16)
O5 C24 H24A 109.5
O5 C24 H24B 109.5
H24A C24 H24B 109.5
O5 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
O2 C21 C22 112.1(2)
O2 C21 H21A 109.2
C22 C21 H21A 109.2
O2 C21 H21B 109.2
C22 C21 H21B 109.2
H21A C21 H21B 107.9
O4 C23 H23A 109.5
O4 C23 H23B 109.5
H23A C23 H23B 109.5
O4 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
C21 C22 H22A 109.5
C21 C22 H22B 109.5
H22A C22 H22B 109.5
C21 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C4 1.3807(17)
N1 C15 1.4236(18)
N1 C1 1.4569(17)
N2 C14 1.341(2)
N2 C10 1.3467(19)
O5 C18 1.3696(18)
O5 C24 1.412(2)
O4 C8 1.312(2)
O4 C23 1.447(3)
O2 C5 1.334(2)
O2 C21 1.462(3)
O1 C5 1.198(2)
O3 C8 1.163(3)
C4 C9 1.3554(17)
C4 C3 1.4982(19)
C10 C11 1.407(2)
C10 C9 1.4533(19)
C9 H9 0.9300
C18 C19 1.3831(19)
C18 C17 1.385(2)
C2 C6 1.5240(19)
C2 C3 1.5345(18)
C2 C1 1.548(2)
C2 H2 0.9800
C15 C20 1.378(2)
C15 C16 1.3933(19)
C6 C7 1.518(2)
C6 H6A 0.9700
C6 H6B 0.9700
C20 C19 1.392(2)
C20 H20 0.9300
C1 C5 1.522(3)
C1 H1 0.9800
C19 H19 0.9300
C3 H3A 0.9700
C3 H3B 0.9700
C16 C17 1.383(2)
C16 H16 0.9300
C11 C12 1.380(2)
C11 H11 0.9300
C7 C8 1.492(2)
C7 H7A 0.9700
C7 H7B 0.9700
C17 H17 0.9300
C13 C14 1.370(3)
C13 C12 1.374(3)
C13 H13 0.9300
C14 H14 0.9300
C12 H12 0.9300
C24 H24A 0.9600
C24 H24B 0.9600
C24 H24C 0.9600
C21 C22 1.469(4)
C21 H21A 0.9700
C21 H21B 0.9700
C23 H23A 0.9600
C23 H23B 0.9600
C23 H23C 0.9600
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
