#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/30/4023025.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_4023025
loop_
_publ_author_name
'Santos Fustero'
'Begoña Fernández'
'Juan F. Sanz-Cervera'
'Natalia Mateu'
'Silvia Mosulén'
'Rodrigo J. Carbajo'
'Antonio Pineda-Lucena'
'Carmen Ramírez de Arellano'
_publ_section_title
;
 Asymmetric Synthesis of Fluorinated Amino Macrolactones
 through Ring-Closing Metathesis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8716
_journal_page_last               8723
_journal_paper_doi               10.1021/jo701484w
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration rm
_chemical_formula_sum            'C17 H19 F2 N O4'
_chemical_formula_weight         339.33
_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   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            4
_cell_length_a                   5.1217(10)
_cell_length_b                   13.763(3)
_cell_length_c                   22.709(5)
_cell_measurement_reflns_used    7033
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     1600.8(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'SHELXTL v6.14 (Bruker 2000-2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0636
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12346
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         5.20
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.8(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0385
_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)+(0.0376P)²+0.1930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0806
_reflns_number_gt                1757
_reflns_number_total             2293
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701484w.cif
_cod_data_source_block           sfbf95
_cod_database_code               4023025
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
_atom_site_refinement_flags
F1 F 0.2358(3) 0.14045(9) 0.96327(5) 0.0363(3) Uani 1 1 d .
F2 F 0.6429(2) 0.15174(9) 0.93591(5) 0.0363(3) Uani 1 1 d .
N1 N 0.3720(4) 0.00940(13) 0.87792(9) 0.0310(4) Uani 1 1 d .
H1 H 0.532(5) -0.0103(18) 0.8830(10) 0.040(7) Uiso 1 1 d .
O1 O 0.0749(4) 0.18014(12) 0.74341(7) 0.0437(4) Uani 1 1 d .
O2 O 0.4384(3) 0.23281(11) 0.78917(6) 0.0340(4) Uani 1 1 d .
O3 O -0.0558(3) -0.03633(10) 0.87676(6) 0.0294(3) Uani 1 1 d .
O4 O 0.2713(3) -0.14101(10) 0.90052(7) 0.0341(4) Uani 1 1 d .
C1 C 0.2134(5) 0.24588(17) 0.75872(9) 0.0353(5) Uani 1 1 d .
C2 C 0.1657(6) 0.35215(17) 0.74867(10) 0.0438(6) Uani 1 1 d .
H2A H -0.0144 0.3614 0.7339 0.053 Uiso 1 1 calc R
H2B H 0.2878 0.3762 0.7182 0.053 Uiso 1 1 calc R
C3 C 0.2023(5) 0.41164(16) 0.80507(10) 0.0375(6) Uani 1 1 d .
H3A H 0.3872 0.4086 0.8177 0.045 Uiso 1 1 calc R
H3B H 0.1580 0.4805 0.7974 0.045 Uiso 1 1 calc R
C4 C 0.0308(5) 0.37282(15) 0.85304(9) 0.0323(5) Uani 1 1 d .
H4 H -0.1480 0.3908 0.8510 0.039 Uiso 1 1 calc R
C5 C 0.0980(4) 0.31604(15) 0.89830(9) 0.0297(5) Uani 1 1 d .
H5 H -0.0397 0.2945 0.9231 0.036 Uiso 1 1 calc R
C6 C 0.3669(4) 0.28280(14) 0.91407(9) 0.0285(5) Uani 1 1 d .
H6A H 0.4162 0.3115 0.9525 0.034 Uiso 1 1 calc R
H6B H 0.4912 0.3072 0.8842 0.034 Uiso 1 1 calc R
C7 C 0.3921(4) 0.17308(15) 0.91800(9) 0.0275(5) Uani 1 1 d .
C8 C 0.3299(4) 0.11130(14) 0.86421(9) 0.0266(5) Uani 1 1 d .
H8 H 0.1411 0.1203 0.8544 0.032 Uiso 1 1 calc R
C9 C 0.4900(5) 0.13550(16) 0.80953(9) 0.0346(5) Uani 1 1 d .
H9A H 0.6781 0.1289 0.8187 0.041 Uiso 1 1 calc R
H9B H 0.4475 0.0887 0.7778 0.041 Uiso 1 1 calc R
C10 C 0.1746(4) -0.05411(15) 0.88469(9) 0.0257(5) Uani 1 1 d .
C11 C 0.2488(4) -0.31005(14) 0.91577(9) 0.0276(5) Uani 1 1 d .
C12 C 0.2055(5) -0.36950(15) 0.96401(9) 0.0338(5) Uani 1 1 d .
H12 H 0.0677 -0.3552 0.9906 0.041 Uiso 1 1 calc R
C13 C 0.3643(5) -0.45049(16) 0.97352(10) 0.0375(6) Uani 1 1 d .
H13 H 0.3320 -0.4918 1.0062 0.045 Uiso 1 1 calc R
C14 C 0.5672(5) -0.47073(15) 0.93581(10) 0.0360(5) Uani 1 1 d .
H14 H 0.6781 -0.5247 0.9431 0.043 Uiso 1 1 calc R
C15 C 0.6091(5) -0.41235(16) 0.88721(10) 0.0375(5) Uani 1 1 d .
H15 H 0.7480 -0.4265 0.8608 0.045 Uiso 1 1 calc R
C16 C 0.4489(5) -0.33339(15) 0.87702(9) 0.0338(5) Uani 1 1 d .
H16 H 0.4761 -0.2945 0.8430 0.041 Uiso 1 1 calc R
C17 C 0.0865(5) -0.22107(14) 0.90517(10) 0.0332(5) Uani 1 1 d .
H17A H -0.0155 -0.2278 0.8684 0.040 Uiso 1 1 calc R
H17B H -0.0358 -0.2102 0.9383 0.040 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'
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
C10 N1 C8 122.7(2)
C1 O2 C9 116.27(18)
C10 O4 C17 116.95(16)
O1 C1 O2 123.3(2)
O1 C1 C2 126.5(2)
O2 C1 C2 110.2(2)
C1 C2 C3 111.97(18)
C4 C3 C2 110.22(19)
C5 C4 C3 128.1(2)
C4 C5 C6 126.9(2)
C5 C6 C7 113.37(18)
F1 C7 F2 104.59(14)
F1 C7 C6 108.58(17)
F2 C7 C6 107.95(17)
F1 C7 C8 107.17(16)
F2 C7 C8 108.21(17)
C6 C7 C8 119.39(16)
N1 C8 C7 109.65(17)
N1 C8 C9 107.80(17)
C7 C8 C9 114.78(17)
O2 C9 C8 111.44(17)
O3 C10 O4 125.1(2)
O3 C10 N1 125.5(2)
O4 C10 N1 109.38(18)
C12 C11 C16 118.9(2)
C12 C11 C17 121.4(2)
C16 C11 C17 119.76(18)
C11 C12 C13 120.0(2)
C14 C13 C12 120.4(2)
C13 C14 C15 119.8(2)
C16 C15 C14 119.9(2)
C15 C16 C11 120.95(19)
O4 C17 C11 105.63(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C7 1.378(2)
F2 C7 1.379(2)
N1 C10 1.345(3)
N1 C8 1.453(3)
O1 C1 1.201(3)
O2 C1 1.356(3)
O2 C9 1.441(3)
O3 C10 1.219(3)
O4 C10 1.344(2)
O4 C17 1.456(3)
C1 C2 1.500(3)
C2 C3 1.532(3)
C3 C4 1.498(3)
C4 C5 1.336(3)
C5 C6 1.495(3)
C6 C7 1.518(3)
C7 C8 1.522(3)
C8 C9 1.525(3)
C11 C12 1.385(3)
C11 C16 1.389(3)
C11 C17 1.499(3)
C12 C13 1.397(3)
C13 C14 1.375(3)
C14 C15 1.382(3)
C15 C16 1.381(3)
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
N1 H1 O3 0.87(3) 2.15(3) 2.998(3) 166(2) 1_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
C9 O2 C1 O1 -7.8(3)
C9 O2 C1 C2 171.23(18)
O1 C1 C2 C3 131.6(2)
O2 C1 C2 C3 -47.5(3)
C1 C2 C3 C4 -55.6(3)
C2 C3 C4 C5 101.6(3)
C3 C4 C5 C6 4.4(4)
C4 C5 C6 C7 -124.0(2)
C5 C6 C7 F1 -63.9(2)
C5 C6 C7 F2 -176.72(16)
C5 C6 C7 C8 59.3(3)
C10 N1 C8 C7 108.1(2)
C10 N1 C8 C9 -126.3(2)
F1 C7 C8 N1 -57.2(2)
F2 C7 C8 N1 55.1(2)
C6 C7 C8 N1 179.0(2)
F1 C7 C8 C9 -178.68(16)
F2 C7 C8 C9 -66.4(2)
C6 C7 C8 C9 57.5(3)
C1 O2 C9 C8 -77.9(2)
N1 C8 C9 O2 173.97(18)
C7 C8 C9 O2 -63.5(2)
C17 O4 C10 O3 3.7(3)
C17 O4 C10 N1 -175.14(17)
C8 N1 C10 O3 4.8(3)
C8 N1 C10 O4 -176.33(18)
C16 C11 C12 C13 1.0(3)
C17 C11 C12 C13 -178.34(19)
C11 C12 C13 C14 1.2(3)
C12 C13 C14 C15 -2.0(3)
C13 C14 C15 C16 0.6(3)
C14 C15 C16 C11 1.6(3)
C12 C11 C16 C15 -2.3(3)
C17 C11 C16 C15 177.0(2)
C10 O4 C17 C11 173.12(17)
C12 C11 C17 O4 124.7(2)
C16 C11 C17 O4 -54.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658598
