#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/27/7052787.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_7052787
loop_
_publ_author_name
'Huang, Yiyong'
'Suzuki, Satoru'
'Liu, Guokai'
'Tokunaga, Etsuko'
'Shiro, Motoo'
'Shibata, Norio'
_publ_section_title
;
 Asymmetric synthesis of chiral trifluoromethylated heliotridane via
 highly catalytic asymmetric Friedel--Crafts alkylation with
 β-trifluoromethylated acrylates and pyrroles
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2614
_journal_paper_doi               10.1039/c1nj20550a
_journal_volume                  35
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H17 F3 N2 O3 '
_chemical_formula_sum            'C18 H17 F3 N2 O3'
_chemical_formula_weight         366.34
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.0681(9)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   10.77497(19)
_cell_length_b                   6.30036(11)
_cell_length_c                   12.5202(7)
_cell_measurement_reflns_used    15209
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      4.1
_cell_volume                     849.40(5)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      93.1
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16058
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_exptl_absorpt_coefficient_mu    1.033
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             380.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.13
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1272 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2971
_refine_ls_R_factor_gt           0.0243
_refine_ls_shift/su_max          0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0329P)²+0.2077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0617
_reflns_number_gt                2914
_reflns_number_total             2971
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c1nj20550a.txt
_cod_data_source_block           '_FC-164'
_cod_original_cell_volume        849.39(5)
_cod_original_formula_sum        'C18 H17 F3 N2 O3 '
_cod_database_code               7052787
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
F1 F 0.31179(7) 0.89469(14) 0.34396(6) 0.02370(19) Uani 1 1 d .
F2 F 0.12286(7) 0.78413(15) 0.34175(6) 0.0282(2) Uani 1 1 d .
F3 F 0.17487(8) 1.06603(13) 0.43025(6) 0.02585(19) Uani 1 1 d .
O1 O 0.18863(10) 0.36331(17) 0.61358(8) 0.0270(2) Uani 1 1 d .
O2 O -0.02549(10) 0.61605(18) 0.87937(8) 0.0284(2) Uani 1 1 d .
O3 O 0.00293(11) 0.86846(17) 0.75823(9) 0.0314(2) Uani 1 1 d .
N1 N 0.35727(10) 0.9999(2) 0.61795(9) 0.0201(2) Uani 1 1 d .
H1N H 0.2976 1.0952 0.6158 0.024 Uiso 1 1 calc R
N2 N 0.09472(10) 0.53351(18) 0.74497(9) 0.0186(2) Uani 1 1 d .
C1 C 0.46860(12) 1.0199(3) 0.67325(11) 0.0226(3) Uani 1 1 d .
H1 H 0.4948 1.1388 0.7149 0.027 Uiso 1 1 calc R
C2 C 0.53547(12) 0.8387(2) 0.65803(11) 0.0233(3) Uani 1 1 d .
H2 H 0.6160 0.8086 0.6875 0.028 Uiso 1 1 calc R
C3 C 0.46276(12) 0.7040(2) 0.59024(11) 0.0215(3) Uani 1 1 d .
H3 H 0.4855 0.5672 0.5658 0.026 Uiso 1 1 calc R
C4 C 0.35349(12) 0.8080(2) 0.56646(10) 0.0185(3) Uani 1 1 d .
C5 C 0.24204(12) 0.7326(2) 0.50177(11) 0.0188(3) Uani 1 1 d .
H5 H 0.2611 0.5868 0.4754 0.023 Uiso 1 1 calc R
C6 C 0.21378(12) 0.8698(2) 0.40507(10) 0.0200(3) Uani 1 1 d .
C7 C 0.12579(12) 0.7159(2) 0.56983(11) 0.0211(3) Uani 1 1 d .
H7A H 0.1166 0.8467 0.6126 0.025 Uiso 1 1 calc R
H7B H 0.0506 0.6993 0.5227 0.025 Uiso 1 1 calc R
C8 C 0.14002(12) 0.5259(2) 0.64307(11) 0.0199(3) Uani 1 1 d .
C9 C 0.02226(13) 0.6923(2) 0.78991(11) 0.0227(3) Uani 1 1 d .
C10 C 0.00292(13) 0.3935(3) 0.89340(11) 0.0257(3) Uani 1 1 d .
H10A H -0.0720 0.3057 0.8787 0.031 Uiso 1 1 calc R
H10B H 0.0342 0.3652 0.9673 0.031 Uiso 1 1 calc R
C11 C 0.10265(13) 0.3439(2) 0.81348(11) 0.0220(3) Uani 1 1 d .
H11 H 0.0774 0.2160 0.7706 0.026 Uiso 1 1 calc R
C12 C 0.23352(13) 0.3091(2) 0.86385(11) 0.0249(3) Uani 1 1 d .
H12A H 0.2330 0.1763 0.9061 0.030 Uiso 1 1 calc R
H12B H 0.2921 0.2887 0.8056 0.030 Uiso 1 1 calc R
C13 C 0.28191(12) 0.4863(2) 0.93529(11) 0.0211(3) Uani 1 1 d .
C14 C 0.26539(12) 0.4787(3) 1.04536(11) 0.0235(3) Uani 1 1 d .
H14 H 0.2238 0.3610 1.0753 0.028 Uiso 1 1 calc R
C15 C 0.30886(13) 0.6404(3) 1.11123(12) 0.0266(3) Uani 1 1 d .
H15 H 0.2961 0.6338 1.1858 0.032 Uiso 1 1 calc R
C16 C 0.37092(13) 0.8120(3) 1.06930(13) 0.0292(3) Uani 1 1 d .
H16 H 0.4003 0.9233 1.1147 0.035 Uiso 1 1 calc R
C17 C 0.38980(13) 0.8198(3) 0.96023(13) 0.0290(3) Uani 1 1 d .
H17 H 0.4338 0.9356 0.9311 0.035 Uiso 1 1 calc R
C18 C 0.34473(12) 0.6591(3) 0.89363(12) 0.0249(3) Uani 1 1 d .
H18 H 0.3568 0.6670 0.8189 0.030 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 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.073 0.053
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, 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
C9 O2 C10 111.35(11)
C1 N1 C4 109.26(11)
C8 N2 C9 128.03(12)
C8 N2 C11 119.64(11)
C9 N2 C11 111.57(11)
C2 C1 N1 108.03(13)
C1 C2 C3 107.51(12)
C4 C3 C2 107.21(13)
N1 C4 C3 107.99(12)
N1 C4 C5 122.88(12)
C3 C4 C5 129.04(14)
C4 C5 C6 112.68(11)
C4 C5 C7 111.90(11)
C6 C5 C7 109.72(11)
F1 C6 F3 106.60(11)
F1 C6 F2 106.41(10)
F3 C6 F2 106.21(11)
F1 C6 C5 112.70(11)
F3 C6 C5 113.17(11)
F2 C6 C5 111.28(12)
C8 C7 C5 108.80(11)
O1 C8 N2 118.70(13)
O1 C8 C7 121.25(12)
N2 C8 C7 120.03(12)
O3 C9 O2 122.94(14)
O3 C9 N2 128.60(14)
O2 C9 N2 108.46(12)
O2 C10 C11 105.67(11)
N2 C11 C10 100.86(11)
N2 C11 C12 112.80(11)
C10 C11 C12 114.62(11)
C13 C12 C11 115.38(12)
C18 C13 C14 118.50(14)
C18 C13 C12 121.17(13)
C14 C13 C12 120.33(14)
C15 C14 C13 120.72(15)
C14 C15 C16 120.50(14)
C15 C16 C17 119.36(14)
C18 C17 C16 120.29(14)
C17 C18 C13 120.61(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C6 1.3355(16)
F2 C6 1.3504(16)
F3 C6 1.3464(17)
O1 C8 1.2140(18)
O2 C9 1.3385(17)
O2 C10 1.4446(19)
O3 C9 1.1943(18)
N1 C1 1.3690(17)
N1 C4 1.3698(19)
N2 C8 1.3832(17)
N2 C9 1.3996(18)
N2 C11 1.4714(18)
C1 C2 1.367(2)
C2 C3 1.416(2)
C3 C4 1.3707(19)
C4 C5 1.5012(18)
C5 C6 1.5098(19)
C5 C7 1.5437(18)
C7 C8 1.512(2)
C10 C11 1.527(2)
C11 C12 1.5395(19)
C12 C13 1.511(2)
C13 C18 1.393(2)
C13 C14 1.397(2)
C14 C15 1.382(2)
C15 C16 1.384(2)
C16 C17 1.389(2)
C17 C18 1.388(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139176095
