#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/59/1505920.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_1505920
loop_
_publ_author_name
'Ting, Amal'
'Lou, Sha'
'Schaus, Scott E.'
_publ_section_title
;
 Highly diastereoselective asymmetric Mannich reactions of 1,3-dicarbonyls
 with acyl imines.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2003
_journal_page_last               2006
_journal_paper_doi               10.1021/ol060304b
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C15 H20 F N O5'
_chemical_formula_sum            'C15 H20 F N O5'
_chemical_formula_weight         313.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_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            4
_cell_length_a                   9.754(2)
_cell_length_b                   12.086(2)
_cell_length_c                   13.614(3)
_cell_measurement_reflns_used    5016
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.27
_cell_volume                     1604.9(6)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_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  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27484
_diffrn_reflns_theta_full        30.53
_diffrn_reflns_theta_max         30.53
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9948
_exptl_absorpt_correction_T_min  0.9595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    isotropic
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.068
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0667P)²+0.0337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                4259
_reflns_number_total             4884
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060304bsi20060204_063216.cif
_cod_data_source_block           schaus11
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1605.0(6)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1505920
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'
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
F1 F 0.29739(10) -0.10324(8) 0.09867(8) 0.0557(3) Uani 1 1 d
O1 O 0.83045(9) -0.01932(9) -0.22457(8) 0.0418(2) Uani 1 1 d
O2 O 0.62051(13) 0.27534(8) -0.29066(8) 0.0477(3) Uani 1 1 d
O3 O 0.81173(10) 0.23246(8) -0.20533(7) 0.0376(2) Uani 1 1 d
O4 O 0.76856(8) 0.27167(8) 0.03994(7) 0.03197(19) Uani 1 1 d
O5 O 0.55770(8) 0.35319(8) 0.04851(8) 0.0383(2) Uani 1 1 d
N1 N 0.58224(9) 0.20561(8) -0.04627(7) 0.02521(19) Uani 1 1 d
H1N H 0.4995(17) 0.2105(12) -0.0515(11) 0.030(4) Uiso 1 1 d
C1 C 0.64886(10) 0.10487(9) -0.08380(8) 0.0240(2) Uani 1 1 d
H1 H 0.7488(13) 0.1185(11) -0.0686(10) 0.020(3) Uiso 1 1 d
C2 C 0.62950(11) 0.10169(9) -0.19791(8) 0.0254(2) Uani 1 1 d
C3 C 0.71350(11) 0.00486(10) -0.24604(8) 0.0277(2) Uani 1 1 d
C4 C 0.62358(14) -0.05331(11) -0.32097(10) 0.0353(3) Uani 1 1 d
H4B H 0.677(2) -0.0828(17) -0.3758(14) 0.057(5) Uiso 1 1 d
H4A H 0.5906(19) -0.1271(15) -0.2861(14) 0.048(5) Uiso 1 1 d
C5 C 0.50179(14) 0.02530(12) -0.33743(9) 0.0371(3) Uani 1 1 d
H5B H 0.5276(18) 0.0796(14) -0.3878(13) 0.040(4) Uiso 1 1 d
H5A H 0.4169(19) -0.0165(14) -0.3568(13) 0.040(4) Uiso 1 1 d
C6 C 0.48193(12) 0.08044(11) -0.23583(9) 0.0320(3) Uani 1 1 d
H6B H 0.4316(16) 0.1458(13) -0.2329(12) 0.035(4) Uiso 1 1 d
H6A H 0.437(2) 0.0340(15) -0.1925(15) 0.045(4) Uiso 1 1 d
C7 C 0.68407(13) 0.21280(10) -0.23808(9) 0.0315(2) Uani 1 1 d
C8 C 0.8676(2) 0.34062(13) -0.22844(13) 0.0492(4) Uani 1 1 d
H8C H 0.815(2) 0.3974(17) -0.1993(16) 0.061(6) Uiso 1 1 d
H8B H 0.953(2) 0.3375(17) -0.2090(17) 0.062(6) Uiso 1 1 d
H8A H 0.863(2) 0.3527(16) -0.3013(17) 0.060(5) Uiso 1 1 d
C9 C 0.59780(11) 0.00049(9) -0.03185(8) 0.0258(2) Uani 1 1 d
C10 C 0.68382(14) -0.09226(12) -0.02303(10) 0.0373(3) Uani 1 1 d
H10 H 0.7743(19) -0.0887(14) -0.0479(13) 0.040(4) Uiso 1 1 d
C11 C 0.63799(17) -0.18824(12) 0.02412(12) 0.0453(3) Uani 1 1 d
H11 H 0.700(2) -0.245(2) 0.0286(16) 0.075(6) Uiso 1 1 d
C12 C 0.50686(17) -0.19374(12) 0.06437(11) 0.0432(3) Uani 1 1 d
H12 H 0.476(2) -0.2529(18) 0.0954(14) 0.062(6) Uiso 1 1 d
C13 C 0.42513(13) -0.10085(12) 0.05674(10) 0.0365(3) Uani 1 1 d
C14 C 0.46637(12) -0.00413(10) 0.00966(9) 0.0298(2) Uani 1 1 d
H14 H 0.405(2) 0.0626(15) 0.0088(13) 0.043(4) Uiso 1 1 d
C15 C 0.64745(11) 0.27584(9) 0.01637(8) 0.0240(2) Uani 1 1 d
C16 C 0.61250(17) 0.43300(17) 0.11690(17) 0.0607(6) Uani 1 1 d
H16C H 0.645(2) 0.3829(18) 0.1729(18) 0.067(7) Uiso 1 1 d
H16B H 0.683(3) 0.479(2) 0.088(2) 0.085(7) Uiso 1 1 d
H16A H 0.540(2) 0.4636(19) 0.1488(15) 0.063(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'
F F 0.0171 0.0103 '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
C7 O3 C8 115.82(12)
C15 O5 C16 115.50(10)
C15 N1 C1 121.82(9)
N1 C1 C9 112.22(8)
N1 C1 C2 108.15(9)
C9 C1 C2 113.53(9)
C7 C2 C6 110.25(10)
C7 C2 C1 106.76(9)
C6 C2 C1 116.51(9)
C7 C2 C3 108.67(9)
C6 C2 C3 102.82(9)
C1 C2 C3 111.66(9)
O1 C3 C4 126.42(11)
O1 C3 C2 124.68(10)
C4 C3 C2 108.89(9)
C3 C4 C5 104.97(10)
C4 C5 C6 103.45(10)
C2 C6 C5 104.63(10)
O2 C7 O3 124.05(12)
O2 C7 C2 125.11(12)
O3 C7 C2 110.83(10)
C14 C9 C10 118.67(11)
C14 C9 C1 121.12(10)
C10 C9 C1 120.20(10)
C11 C10 C9 120.65(12)
C12 C11 C10 120.88(13)
C13 C12 C11 117.50(13)
F1 C13 C12 118.44(13)
F1 C13 C14 118.16(12)
C12 C13 C14 123.40(12)
C13 C14 C9 118.88(11)
O4 C15 O5 124.57(10)
O4 C15 N1 126.09(10)
O5 C15 N1 109.33(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C13 1.3709(15)
O1 C3 1.2134(15)
O2 C7 1.2117(16)
O3 C7 1.3438(17)
O3 C8 1.4508(17)
O4 C15 1.2252(14)
O5 C15 1.3534(13)
O5 C16 1.4434(16)
N1 C15 1.3610(14)
N1 C1 1.4716(14)
C1 C9 1.5297(16)
C1 C2 1.5655(15)
C2 C7 1.5445(17)
C2 C6 1.5507(16)
C2 C3 1.5718(15)
C3 C4 1.5179(17)
C4 C5 1.5376(19)
C5 C6 1.5476(17)
C9 C14 1.4021(16)
C9 C10 1.4053(17)
C10 C11 1.399(2)
C11 C12 1.393(2)
C12 C13 1.381(2)
C13 C14 1.3925(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21199851
