#------------------------------------------------------------------------------
#$Date: 2021-10-16 00:57:35 +0300 (Sat, 16 Oct 2021) $
#$Revision: 269971 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/91/7129121.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_7129121
loop_
_publ_author_name
'Alberca, Saul'
'Matador, Esteban'
'Iglesias-Sigüenza, Javier'
'Retamosa, Maria de Gracia'
'Fernández, Rosario'
'Lassaletta, Jose M.'
'Monge, David'
_publ_section_title
;
 Asymmetric cross-aldol reaction of α-keto hydrazones and
 α,β-unsaturated γ-keto hydrazones with trifluoromethyl ketones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05014A
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H17 F3 N2 O2'
_chemical_formula_weight         350.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2021-07-21 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.836(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0402(5)
_cell_length_b                   6.9374(3)
_cell_length_c                   11.4994(5)
_cell_measurement_reflns_used    3803
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.77
_cell_measurement_theta_min      6.84
_cell_volume                     828.49(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-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5218
_diffrn_reflns_point_group_measured_fraction_full 0.750
_diffrn_reflns_point_group_measured_fraction_max 0.750
_diffrn_reflns_theta_full        65.751
_diffrn_reflns_theta_max         65.751
_diffrn_reflns_theta_min         6.839
_exptl_absorpt_coefficient_mu    0.984
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.6001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical 
 X-ray Solutions, Madison, Wisconsin, USA. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       Prism
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   0.13(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.663
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2156
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.663
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.5844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.415
_reflns_Friedel_fraction_full    0.484
_reflns_Friedel_fraction_max     0.484
_reflns_number_gt                2152
_reflns_number_total             2156
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc05014a2.cif
_cod_data_source_block           igl1120
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7129121
_shelx_shelxl_version_number     2018/1
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.744
_shelx_estimated_absorpt_t_max   0.917
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5842(2) 0.6083(4) 0.6773(2) 0.0224(6) Uani 1 1 d . . . . .
H1 H 0.636663 0.655298 0.635291 0.027 Uiso 1 1 calc R U . . .
C2 C 0.4849(2) 0.4814(5) 0.6184(2) 0.0268(6) Uani 1 1 d . . . . .
H2 H 0.471663 0.443240 0.537490 0.032 Uiso 1 1 calc R U . . .
C3 C 0.4054(2) 0.4115(4) 0.6798(2) 0.0277(6) Uani 1 1 d . . . . .
H3 H 0.338642 0.327243 0.640038 0.033 Uiso 1 1 calc R U . . .
C4 C 0.4259(2) 0.4677(4) 0.8003(2) 0.0270(6) Uani 1 1 d . . . . .
H4 H 0.372927 0.420940 0.841796 0.032 Uiso 1 1 calc R U . . .
C5 C 0.5257(2) 0.5941(4) 0.8597(2) 0.0230(6) Uani 1 1 d . . . . .
H5 H 0.539063 0.631172 0.940844 0.028 Uiso 1 1 calc R U . . .
C6 C 0.6056(2) 0.6653(4) 0.7986(2) 0.0201(5) Uani 1 1 d . . . . .
C7 C 0.7137(2) 0.8070(4) 0.86528(19) 0.0186(5) Uani 1 1 d . . . . .
C8 C 0.6636(2) 1.0123(4) 0.8289(2) 0.0221(6) Uani 1 1 d . . . . .
C9 C 0.8356(2) 0.7712(4) 0.83069(19) 0.0206(5) Uani 1 1 d . . . . .
H9A H 0.848643 0.633136 0.828537 0.025 Uiso 1 1 calc R U . . .
H9B H 0.819890 0.820177 0.747851 0.025 Uiso 1 1 calc R U . . .
C10 C 0.9591(2) 0.8614(4) 0.91640(19) 0.0207(5) Uani 1 1 d . . . . .
C11 C 1.0652(2) 0.8940(4) 0.8709(2) 0.0201(5) Uani 1 1 d . . . . .
H11 H 1.145286 0.933049 0.924542 0.024 Uiso 1 1 calc R U . . .
C12 C 1.2695(2) 0.9575(4) 0.7945(2) 0.0242(6) Uani 1 1 d . . . . .
H12A H 1.260256 1.070634 0.838790 0.036 Uiso 1 1 calc R U . . .
H12B H 1.323560 0.986245 0.746610 0.036 Uiso 1 1 calc R U . . .
H12C H 1.307897 0.856240 0.852112 0.036 Uiso 1 1 calc R U . . .
C13 C 1.1158(2) 0.8760(4) 0.5827(2) 0.0182(5) Uani 1 1 d . . . . .
C14 C 1.2137(2) 0.8299(4) 0.5372(2) 0.0224(5) Uani 1 1 d . . . . .
H14 H 1.297241 0.811243 0.591305 0.027 Uiso 1 1 calc R U . . .
C15 C 1.1866(3) 0.8119(4) 0.4104(2) 0.0272(6) Uani 1 1 d . . . . .
H15 H 1.252324 0.781478 0.380020 0.033 Uiso 1 1 calc R U . . .
C16 C 1.0622(3) 0.8389(4) 0.3287(2) 0.0280(6) Uani 1 1 d . . . . .
H16 H 1.044109 0.826711 0.243957 0.034 Uiso 1 1 calc R U . . .
C17 C 0.9653(2) 0.8844(4) 0.3755(2) 0.0258(6) Uani 1 1 d . . . . .
H17 H 0.881762 0.902200 0.321184 0.031 Uiso 1 1 calc R U . . .
C18 C 0.9900(2) 0.9039(4) 0.5011(2) 0.0214(5) Uani 1 1 d . . . . .
H18 H 0.924090 0.935150 0.530976 0.026 Uiso 1 1 calc R U . . .
F1 F 0.62001(14) 1.0383(2) 0.70578(12) 0.0304(4) Uani 1 1 d . . . . .
F2 F 0.56579(13) 1.0542(3) 0.86876(13) 0.0303(4) Uani 1 1 d . . . . .
F3 F 0.75510(13) 1.1465(2) 0.87621(14) 0.0297(4) Uani 1 1 d . . . . .
N1 N 1.04669(17) 0.8677(3) 0.75434(16) 0.0182(4) Uani 1 1 d . . . . .
N2 N 1.14318(17) 0.8957(3) 0.71231(16) 0.0192(4) Uani 1 1 d . . . . .
O1 O 0.74002(15) 0.7906(3) 0.99414(13) 0.0226(4) Uani 1 1 d . . . . .
H1A H 0.812361 0.832386 1.031168 0.034 Uiso 1 1 calc R U . . .
O2 O 0.97430(15) 0.8992(3) 1.02495(14) 0.0265(4) Uani 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
C2 C1 C6 120.4(2) . . ?
C3 C2 C1 120.3(2) . . ?
C2 C3 C4 119.6(2) . . ?
C3 C4 C5 120.2(2) . . ?
C4 C5 C6 120.5(2) . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 C7 119.6(2) . . ?
C1 C6 C7 121.5(2) . . ?
O1 C7 C6 108.68(19) . . ?
O1 C7 C8 106.7(2) . . ?
C6 C7 C8 108.13(18) . . ?
O1 C7 C9 111.64(17) . . ?
C6 C7 C9 111.4(2) . . ?
C8 C7 C9 110.1(2) . . ?
F2 C8 F3 107.1(2) . . ?
F2 C8 F1 106.81(18) . . ?
F3 C8 F1 106.5(2) . . ?
F2 C8 C7 111.5(2) . . ?
F3 C8 C7 112.35(19) . . ?
F1 C8 C7 112.3(2) . . ?
C10 C9 C7 115.72(19) . . ?
O2 C10 C11 118.9(2) . . ?
O2 C10 C9 122.0(2) . . ?
C11 C10 C9 119.06(19) . . ?
N1 C11 C10 119.0(2) . . ?
C14 C13 C18 120.0(2) . . ?
C14 C13 N2 120.1(2) . . ?
C18 C13 N2 119.9(2) . . ?
C15 C14 C13 119.8(2) . . ?
C14 C15 C16 120.6(2) . . ?
C17 C16 C15 119.0(2) . . ?
C18 C17 C16 121.5(2) . . ?
C17 C18 C13 119.1(2) . . ?
C11 N1 N2 119.42(18) . . ?
N1 N2 C13 117.15(17) . . ?
N1 N2 C12 121.15(17) . . ?
C13 N2 C12 121.56(18) . . ?
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
C1 C2 1.390(4) . ?
C1 C6 1.391(3) . ?
C2 C3 1.387(4) . ?
C3 C4 1.382(4) . ?
C4 C5 1.392(4) . ?
C5 C6 1.392(3) . ?
C6 C7 1.535(3) . ?
C7 O1 1.414(2) . ?
C7 C8 1.534(4) . ?
C7 C9 1.548(3) . ?
C8 F2 1.340(3) . ?
C8 F3 1.345(3) . ?
C8 F1 1.344(3) . ?
C9 C10 1.520(3) . ?
C10 O2 1.230(3) . ?
C10 C11 1.454(3) . ?
C11 N1 1.298(3) . ?
C12 N2 1.459(3) . ?
C13 C14 1.389(3) . ?
C13 C18 1.401(3) . ?
C13 N2 1.423(3) . ?
C14 C15 1.391(3) . ?
C15 C16 1.388(4) . ?
C16 C17 1.388(4) . ?
C17 C18 1.382(3) . ?
N1 N2 1.325(3) . ?
