#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/21/7052117.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_7052117
loop_
_publ_author_name
'Alberto Avenoza'
'Jesús H. Busto'
'Noelia Canal'
'José I. García'
'Gonzalo Jiménez-Osés'
'Jesús M. Peregrina'
'Marta Pérez-Fernández'
_publ_section_title
;
 Mechanistic study of the ring-size modulation in Michael?Dieckmann
 type reactions of 2-acylaminoacrylates with ketene diethyl acetal
;
_journal_issue                   2
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              224
_journal_paper_doi               10.1039/b615220a
_journal_volume                  31
_journal_year                    2007
_chemical_formula_sum            'C12 H14 F3 N O5'
_chemical_formula_weight         309.24
_chemical_name_common            mar147
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                69.2894(10)
_cell_angle_beta                 82.1053(10)
_cell_angle_gamma                77.1832(14)
_cell_formula_units_Z            2
_cell_length_a                   8.3685(2)
_cell_length_b                   9.1253(2)
_cell_length_c                   9.7248(3)
_cell_measurement_reflns_used    7284
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      0.21
_cell_volume                     675.92(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski , 1997'
_computing_molecular_graphics    ORTEP-III
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9439
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0542
_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)+(0.0374P)²+0.1912P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                2495
_reflns_number_total             3169
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b615220a.txt
_cod_data_source_block           publication_text
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_formula_sum        'C12 H14 F3 N1 O5'
_cod_database_code               7052117
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
N1 N 0.79895(13) 0.26156(13) 0.20150(11) 0.0240(2) Uani 1 1 d . . .
H1 H 0.8988 0.2413 0.1593 0.029 Uiso 1 1 d R . .
O2 O 1.02712(11) 0.34247(11) 0.37468(10) 0.0268(2) Uani 1 1 d . . .
F3 F 0.88550(11) -0.02217(11) 0.13978(11) 0.0473(3) Uani 1 1 d . . .
O4 O 0.87679(12) 0.76402(12) -0.06408(11) 0.0327(2) Uani 1 1 d . . .
O5 O 0.66931(13) 0.35684(12) 0.53349(11) 0.0340(2) Uani 1 1 d . . .
O6 O 0.54865(12) 0.18706(13) 0.26277(11) 0.0351(3) Uani 1 1 d . . .
O7 O 0.78955(12) 0.12991(11) 0.49122(10) 0.0303(2) Uani 1 1 d . . .
C8 C 0.92656(15) 0.43593(15) 0.26945(14) 0.0234(3) Uani 1 1 d . . .
C9 C 0.68512(16) 0.17941(16) 0.20121(14) 0.0259(3) Uani 1 1 d . . .
F10 F 0.63354(13) -0.02402(13) 0.12579(13) 0.0560(3) Uani 1 1 d . . .
C11 C 0.83978(16) 0.65742(16) 0.04735(14) 0.0263(3) Uani 1 1 d . . .
C12 C 0.95623(16) 0.56831(15) 0.15906(14) 0.0261(3) Uani 1 1 d . . .
H12 H 1.0563 0.6056 0.1537 0.031 Uiso 1 1 d R . .
F13 F 0.75027(14) 0.15619(13) -0.03549(10) 0.0551(3) Uani 1 1 d . . .
C14 C 0.62874(16) 0.51329(16) 0.22651(15) 0.0267(3) Uani 1 1 d . . .
H14A H 0.5306 0.4741 0.2289 0.032 Uiso 1 1 d R . .
H14B H 0.6099 0.5795 0.2871 0.032 Uiso 1 1 d R . .
C15 C 0.76909(15) 0.37170(15) 0.28564(14) 0.0229(3) Uani 1 1 d . . .
C16 C 0.73368(16) 0.28571(16) 0.45194(14) 0.0247(3) Uani 1 1 d . . .
C17 C 0.67283(17) 0.61348(17) 0.06881(15) 0.0299(3) Uani 1 1 d . . .
H17A H 0.5907 0.7089 0.0423 0.036 Uiso 1 1 d R . .
H17B H 0.6690 0.5522 0.0073 0.036 Uiso 1 1 d R . .
C18 C 1.18577(17) 0.38249(18) 0.37476(16) 0.0315(3) Uani 1 1 d . . .
H18A H 1.2528 0.3720 0.2891 0.038 Uiso 1 1 d R . .
H18B H 1.1703 0.4904 0.3735 0.038 Uiso 1 1 d R . .
C19 C 0.73929(18) 0.06995(18) 0.10742(16) 0.0314(3) Uani 1 1 d . . .
C20 C 1.26226(18) 0.26853(19) 0.51326(16) 0.0357(3) Uani 1 1 d . . .
H20A H 1.3679 0.2905 0.5183 0.043 Uiso 1 1 d R . .
H20B H 1.2748 0.1615 0.5128 0.043 Uiso 1 1 d R . .
H20C H 1.1924 0.2799 0.5972 0.043 Uiso 1 1 d R . .
C21 C 0.7749(2) 0.04273(19) 0.64825(16) 0.0406(4) Uani 1 1 d . . .
H21A H 0.8186 -0.0684 0.6657 0.049 Uiso 1 1 d R . .
H21B H 0.6613 0.0559 0.6830 0.049 Uiso 1 1 d R . .
H21C H 0.8352 0.0829 0.6997 0.049 Uiso 1 1 d 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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C15 121.07(11) . . ?
C9 N1 H1 120.0 . . ?
C15 N1 H1 118.6 . . ?
C8 O2 C18 119.04(10) . . ?
C16 O7 C21 115.51(11) . . ?
O2 C8 C12 126.47(12) . . ?
O2 C8 C15 111.14(10) . . ?
C12 C8 C15 122.37(11) . . ?
O6 C9 N1 126.79(13) . . ?
O6 C9 C19 119.77(12) . . ?
N1 C9 C19 113.42(11) . . ?
O4 C11 C12 121.24(12) . . ?
O4 C11 C17 120.36(12) . . ?
C12 C11 C17 118.38(11) . . ?
C8 C12 C11 121.58(12) . . ?
C8 C12 H12 119.7 . . ?
C11 C12 H12 118.7 . . ?
C17 C14 C15 110.69(11) . . ?
C17 C14 H14A 109.3 . . ?
C15 C14 H14A 109.4 . . ?
C17 C14 H14B 108.6 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 109.5 . . ?
N1 C15 C8 107.13(10) . . ?
N1 C15 C14 111.97(11) . . ?
C8 C15 C14 108.51(10) . . ?
N1 C15 C16 111.84(10) . . ?
C8 C15 C16 107.13(10) . . ?
C14 C15 C16 110.04(10) . . ?
O5 C16 O7 125.59(12) . . ?
O5 C16 C15 122.08(12) . . ?
O7 C16 C15 112.25(11) . . ?
C11 C17 C14 113.85(11) . . ?
C11 C17 H17A 109.4 . . ?
C14 C17 H17A 107.7 . . ?
C11 C17 H17B 109.3 . . ?
C14 C17 H17B 107.0 . . ?
H17A C17 H17B 109.5 . . ?
O2 C18 C20 106.94(11) . . ?
O2 C18 H18A 109.5 . . ?
C20 C18 H18A 111.0 . . ?
O2 C18 H18B 109.4 . . ?
C20 C18 H18B 110.5 . . ?
H18A C18 H18B 109.5 . . ?
F10 C19 F3 107.64(12) . . ?
F10 C19 F13 107.68(12) . . ?
F3 C19 F13 107.01(12) . . ?
F10 C19 C9 111.36(11) . . ?
F3 C19 C9 112.38(11) . . ?
F13 C19 C9 110.56(12) . . ?
C18 C20 H20A 110.0 . . ?
C18 C20 H20B 109.0 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.4 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O7 C21 H21A 109.3 . . ?
O7 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O7 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.3373(17) . ?
N1 C15 1.4683(17) . ?
N1 H1 0.8896 . ?
O2 C8 1.3355(16) . ?
O2 C18 1.4531(15) . ?
F3 C19 1.3285(17) . ?
O4 C11 1.2298(16) . ?
O5 C16 1.1968(16) . ?
O6 C9 1.2140(16) . ?
O7 C16 1.3250(16) . ?
O7 C21 1.4534(16) . ?
C8 C12 1.3475(18) . ?
C8 C15 1.5248(17) . ?
C9 C19 1.538(2) . ?
F10 C19 1.3173(17) . ?
C11 C12 1.4510(19) . ?
C11 C17 1.5051(19) . ?
C12 H12 0.9600 . ?
F13 C19 1.3352(17) . ?
C14 C17 1.5253(18) . ?
C14 C15 1.5382(18) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9599 . ?
C15 C16 1.5469(18) . ?
C17 H17A 0.9601 . ?
C17 H17B 0.9601 . ?
C18 C20 1.502(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9601 . ?
C20 H20A 0.9601 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9599 . ?
C21 H21A 0.9601 . ?
C21 H21B 0.9599 . ?
C21 H21C 0.9599 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13171961
2 PubChem 139175779
