Supplementary Material (ESI) for Chemical Communications
This journal is (C) The Royal Society of Chemistry

data_global

_publ_contact_author_email       UNEYAMAK@CC.OKAYAMA-U.AC.JP
_publ_contact_author_name        'ProfD Kenji Uneyama'
_journal_name_full               Chem.Commun.
_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_year                    ?
_journal_page_first              ?

_publ_contact_author             
;
ProfD Kenji Uneyama
Department of Applied Chemistry, Faculty of Engineering
Okayama University
Tsushimanaka 3-1-1, Okayama
Okayama
700-8530
JAPAN

;
_publ_contact_letter             
;
ENTER TEXT OF LETTER
;

_publ_section_title              
;
Unusual reactions of N-allylic difluoroenamines under thermal conditions
;

_publ_section_abstract           
;
ENTER ABSTRACT
;

_publ_section_experimental       
;
ENTER EXPERIMENTAL SECTION
;

_publ_section_comment            
;
ENTER TEXT
;

_publ_section_references         
;
ENTER OTHER REFERENCES
Molecular Structure Corporation. (1995). teXsan.=20
Single Crystal Structure Analysis Software. Version 1.7.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
;

_publ_section_acknowledgements   
;
ENTER ACKNOWLEDGEMENTS
;

_publ_section_table_legends      
;
ENTER TABLE LEGENDS
;

_publ_section_figure_captions    
;
ENTER FIGURE CAPTIONS
;
loop_
_publ_author_name
'Kenji Uneyama'
'Yutaka Ichihara'
'Takeshi Kobayashi'
'Takashi Nakagawa'

data_Compound_4c_(R3==Ph)
_database_code_CSD               217315
#--------------------------------------------------------------------------=
_audit_creation_date             'Wed Jun 26 23:37:34 2003'
_audit_creation_method           'from TEXRAY.INF file'
_audit_update_record             ?
#--------------------------------------------------------------------------=
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_reduction        teXsan
_computing_structure_solution    ?
_computing_structure_refinement  teXsan
_computing_publication_material  teXsan
_computing_molecular_graphics    ?
#--------------------------------------------------------------------------=
_chemical_compound_source        ?
_chemical_name_common            ?
_chemical_formula_weight         301.34
_chemical_formula_analytical     ?
_chemical_formula_sum            'C18 H17 F2 N O '
_chemical_formula_moiety         'C18 H17 F2 N O '
_chemical_formula_structural     ?
_chemical_melting_point          ?
#--------------------------------------------------------------------------=
_cell_length_a                   9.4898(5)
_cell_length_b                   21.309(1)
_cell_length_c                   7.9275(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.690(4)
_cell_angle_gamma                90
_cell_volume                     1527.3(1)
_cell_formula_units_Z            4
_cell_measurement_temperature    296.2
_cell_measurement_reflns_used    4196
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      27.5
#--------------------------------------------------------------------------=
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C c          '
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2+x,1/2-y,1/2+z
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_F_000             632.00
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_max  1.255
_exptl_absorpt_correction_T_min  0.842
_exptl_special_details           
;
?
;
#--------------------------------------------------------------------------=
_diffrn_special_details          
;
?
;
_diffrn_ambient_temperature      296.2
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K=A5a'
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_detector       'Imaging Plate'
_diffrn_measurement_device       'Rigaku RAXIS-IV'
_diffrn_measurement_method       =20
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0.00
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
_diffrn_reflns_number            1688
_reflns_number_total             1688
_reflns_number_observed          1490
_reflns_observed_criterion       >3.0sigma(I)
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_av_sigmaI/netI    0.023
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         0.00
_diffrn_reflns_theta_max         0.00
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_orient_matrix_UB_11      -0.09328
_diffrn_orient_matrix_UB_12      -0.02520
_diffrn_orient_matrix_UB_13      -0.03599
_diffrn_orient_matrix_UB_21      0.05926
_diffrn_orient_matrix_UB_22      -0.03955
_diffrn_orient_matrix_UB_23      0.02792
_diffrn_orient_matrix_UB_31      -0.00452
_diffrn_orient_matrix_UB_32      0.00158
_diffrn_orient_matrix_UB_33      0.12432
#--------------------------------------------------------------------------=
#---
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 72 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0 68 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N 0 4 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O 0 4 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
F 0 8 0.017 0.010
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
#--------------------------------------------------------------------------=
#---
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_occupancy
_atom_site_refinement_flags
F(2) 0.569(1) 0.28157(9) 1.056(1) 0.0915(8) Uani d . 1.00 .
F(3) 0.354(1) 0.2360(1) 0.972(1) 0.0924(8) Uani d . 1.00 .
O(1) 1.109(1) 0.0094(1) 0.847(1) 0.0621(6) Uani d . 1.00 .
N(2) 0.699(1) 0.18704(9) 0.927(1) 0.0431(5) Uani d . 1.00 .
C(1) 0.555(1) 0.1294(1) 1.104(1) 0.0391(5) Uani d . 1.00 .
C(2) 0.926(1) 0.1571(1) 0.870(1) 0.0467(6) Uani d . 1.00 .
C(4) 0.769(1) 0.0755(1) 0.912(1) 0.0426(5) Uani d . 1.00 .
C(5) 1.001(1) 0.0495(1) 0.864(1) 0.0451(5) Uani d . 1.00 .
C(6) 0.555(1) 0.1701(1) 0.952(1) 0.0435(5) Uani d . 1.00 .
C(7) 0.871(1) 0.0307(1) 0.894(1) 0.0475(6) Uani d . 1.00 .
C(8) 0.661(1) 0.1385(1) 1.267(1) 0.0464(6) Uani d . 1.00 .
C(9) 1.026(1) 0.1129(1) 0.850(1) 0.0507(6) Uani d . 1.00 .
C(10) 0.444(1) 0.0852(1) 1.093(1) 0.0522(6) Uani d . 1.00 .
C(11) 0.652(1) 0.2344(1) 0.780(1) 0.0672(9) Uani d . 1.00 .
C(12) 0.490(1) 0.2367(2) 0.946(1) 0.0676(8) Uani d . 1.00 .
C(13) 0.544(1) 0.0615(1) 1.400(1) 0.0644(8) Uani d . 1.00 .
C(14) 0.656(1) 0.1045(1) 1.415(1) 0.0585(7) Uani d . 1.00 .
C(15) 0.440(1) 0.0517(1) 1.240(1) 0.0629(8) Uani d . 1.00 .
C(16) 1.089(1) -0.0555(2) 0.872(1) 0.0700(9) Uani d . 1.00 .
C(17) 0.449(1) 0.1640(2) 0.758(1) 0.0659(7) Uani d . 1.00 .
C(18) 0.486(1) 0.2360(2) 0.754(1) 0.0806(9) Uani d . 1.00 .
C(19) 0.795(1) 0.1392(1) 0.903(1) 0.0380(5) Uani d . 1.00 .
H(1) 0.9483 0.2004 0.8625 0.0560 Uiso calc . 1.00 .
H(2) 0.6814 0.0620 0.9317 0.0511 Uiso calc . 1.00 .
H(3) 0.8525 -0.0127 0.9020 0.0571 Uiso calc . 1.00 .
H(4) 0.7400 0.1681 1.2780 0.0556 Uiso calc . 1.00 .
H(5) 1.1155 0.1262 0.8264 0.0608 Uiso calc . 1.00 .
H(6) 0.3726 0.0781 0.9828 0.0627 Uiso calc . 1.00 .
H(7) 0.5421 0.0385 1.5016 0.0773 Uiso calc . 1.00 .
H(8) 0.7305 0.1110 1.5257 0.0702 Uiso calc . 1.00 .
H(9) 0.3654 0.0218 1.2308 0.0755 Uiso calc . 1.00 .
H(10) 0.4842 0.1379 0.6813 0.0790 Uiso calc . 1.00 .
H(11) 0.3505 0.1541 0.7473 0.0790 Uiso calc . 1.00 .
H(12) 0.6981 0.2742 0.8140 0.0806 Uiso calc . 1.00 .
H(13) 0.6742 0.2205 0.6759 0.0806 Uiso calc . 1.00 .
H(14) 0.4242 0.2634 0.6704 0.0967 Uiso calc . 1.00 .
H(15) 1.0853 -0.0623 0.9884 0.0840 Uiso calc . 1.00 .
H(16) 1.0019 -0.0694 0.7881 0.0840 Uiso calc . 1.00 .
H(17) 1.1721 -0.0783 0.8567 0.0840 Uiso calc . 1.00 .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
F(2) 0.152(2) 0.0508(9) 0.095(1) 0.020(1) 0.073(2) -0.0010(8)
F(3) 0.094(1) 0.118(2) 0.086(1) 0.065(1) 0.059(1) 0.036(1)
O(1) 0.0463(10) 0.066(1) 0.085(1) 0.0116(8) 0.0372(9) 0.0020(10)
N(2) 0.050(1) 0.0432(9) 0.0424(9) 0.0052(8) 0.0230(8) 0.0037(7)
C(1) 0.0366(9) 0.0430(10) 0.0429(10) 0.0049(8) 0.0199(7) -0.0032(8)
C(2) 0.046(1) 0.051(1) 0.050(1) -0.0072(9) 0.0235(10) 0.0002(9)
C(4) 0.037(1) 0.0443(10) 0.053(1) -0.0025(9) 0.0237(9) -0.0042(9)
C(5) 0.0364(10) 0.056(1) 0.047(1) 0.0024(9) 0.0190(8) -0.0014(9)
C(6) 0.042(1) 0.054(1) 0.0370(9) 0.0093(9) 0.0168(8) 0.0019(8)
C(7) 0.041(1) 0.044(1) 0.064(1) 0.0000(9) 0.0266(10) -0.0021(10)
C(8) 0.053(1) 0.048(1) 0.0398(10) -0.0042(10) 0.0167(8) -0.0025(8)
C(9) 0.040(1) 0.058(1) 0.061(1) -0.0061(10) 0.0259(10) 0.000(1)
C(10) 0.038(1) 0.054(1) 0.067(1) -0.0024(9) 0.0204(10) -0.010(1)
C(11) 0.093(2) 0.059(2) 0.065(2) 0.027(1) 0.048(2) 0.027(1)
C(12) 0.089(2) 0.067(1) 0.062(1) 0.041(1) 0.044(1) 0.019(1)
C(13) 0.089(2) 0.049(1) 0.074(2) 0.010(1) 0.053(1) 0.011(1)
C(14) 0.079(2) 0.060(1) 0.041(1) 0.007(1) 0.026(1) 0.0029(10)
C(15) 0.065(2) 0.052(1) 0.091(2) -0.006(1) 0.051(1) 0.000(1)
C(16) 0.068(2) 0.066(1) 0.086(2) 0.022(1) 0.040(2) 0.009(2)
C(17) 0.049(1) 0.110(2) 0.038(1) 0.021(1) 0.0136(9) 0.004(1)
C(18) 0.090(2) 0.105(2) 0.059(1) 0.054(2) 0.040(2) 0.039(2)
C(19) 0.0387(10) 0.0444(9) 0.0331(9) -0.0004(8) 0.0142(7) -0.0006(7)
#--------------------------------------------------------------------------=
#---
_refine_special_details          
;
?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      'w == 1/[=A5s^2^(Fo) + 0.00090|Fo|^2^]'
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         1490
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          ?
_refine_ls_R_factor_obs          0.0398
_refine_ls_wR_factor_all         ?
_refine_ls_wR_factor_obs         0.0843
_refine_ls_goodness_of_fit_all   ?
_refine_ls_goodness_of_fit_obs   2.375
_refine_ls_shift/esd_max         0.0020
_refine_ls_shift/esd_mean        0.0010
_refine_diff_density_min         -0.15
_refine_diff_density_max         0.09
#--------------------------------------------------------------------------=
_geom_special_details            
;
?
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F(2) C(12) 1.358(7) 1_555 1_555 yes
F(3) C(12) 1.368(6) 1_555 1_555 yes
O(1) C(5) 1.373(4) 1_555 1_555 yes
O(1) C(16) 1.418(7) 1_555 1_555 yes
N(2) C(6) 1.481(5) 1_555 1_555 yes
N(2) C(11) 1.507(5) 1_555 1_555 yes
N(2) C(19) 1.419(4) 1_555 1_555 yes
C(1) C(6) 1.488(5) 1_555 1_555 yes
C(1) C(8) 1.389(5) 1_555 1_555 yes
C(1) C(10) 1.395(5) 1_555 1_555 yes
C(2) C(9) 1.383(5) 1_555 1_555 yes
C(2) C(19) 1.397(5) 1_555 1_555 yes
C(4) C(7) 1.398(5) 1_555 1_555 yes
C(4) C(19) 1.385(5) 1_555 1_555 yes
C(5) C(7) 1.383(5) 1_555 1_555 yes
C(5) C(9) 1.383(6) 1_555 1_555 yes
C(6) C(12) 1.543(6) 1_555 1_555 yes
C(6) C(17) 1.566(5) 1_555 1_555 yes
C(8) C(14) 1.390(6) 1_555 1_555 yes
C(10) C(15) 1.381(7) 1_555 1_555 yes
C(11) C(18) 1.523(8) 1_555 1_555 yes
C(12) C(18) 1.510(7) 1_555 1_555 yes
C(13) C(14) 1.377(7) 1_555 1_555 yes
C(13) C(15) 1.367(8) 1_555 1_555 yes
C(17) C(18) 1.577(10) 1_555 1_555 yes
#--------------------------------------------------------------------------=
#---
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(5) O(1) C(16) 117.3(3) 1_555 1_555 1_555 yes
C(6) N(2) C(11) 101.3(3) 1_555 1_555 1_555 yes
C(6) N(2) C(19) 119.9(3) 1_555 1_555 1_555 yes
C(11) N(2) C(19) 115.3(3) 1_555 1_555 1_555 yes
C(6) C(1) C(8) 119.7(3) 1_555 1_555 1_555 yes
C(6) C(1) C(10) 121.9(3) 1_555 1_555 1_555 yes
C(8) C(1) C(10) 118.2(3) 1_555 1_555 1_555 yes
C(9) C(2) C(19) 121.2(3) 1_555 1_555 1_555 yes
C(9) C(2) H(1) 118.6(10) 1_555 1_555 1_555 no
C(19) C(2) H(1) 120.2(9) 1_555 1_555 1_555 no
C(7) C(4) C(19) 121.6(3) 1_555 1_555 1_555 yes
C(7) C(4) H(2) 118.9(4) 1_555 1_555 1_555 no
C(19) C(4) H(2) 119.5(4) 1_555 1_555 1_555 no
O(1) C(5) C(7) 124.6(3) 1_555 1_555 1_555 yes
O(1) C(5) C(9) 116.4(3) 1_555 1_555 1_555 yes
C(7) C(5) C(9) 118.9(3) 1_555 1_555 1_555 yes
N(2) C(6) C(1) 118.4(3) 1_555 1_555 1_555 yes
N(2) C(6) C(12) 98.7(3) 1_555 1_555 1_555 yes
N(2) C(6) C(17) 103.7(3) 1_555 1_555 1_555 yes
C(1) C(6) C(12) 117.5(3) 1_555 1_555 1_555 yes
C(1) C(6) C(17) 126.1(4) 1_555 1_555 1_555 yes
C(12) C(6) C(17) 85.1(3) 1_555 1_555 1_555 yes
C(4) C(7) C(5) 120.0(3) 1_555 1_555 1_555 yes
C(4) C(7) H(3) 120.8(9) 1_555 1_555 1_555 no
C(5) C(7) H(3) 119.1(9) 1_555 1_555 1_555 no
C(1) C(8) C(14) 120.5(4) 1_555 1_555 1_555 yes
C(1) C(8) H(4) 119.9(9) 1_555 1_555 1_555 no
C(14) C(8) H(4) 119.6(9) 1_555 1_555 1_555 no
C(2) C(9) C(5) 120.8(3) 1_555 1_555 1_555 yes
C(2) C(9) H(5) 119.8(5) 1_555 1_555 1_555 no
C(5) C(9) H(5) 119.3(4) 1_555 1_555 1_555 no
C(1) C(10) C(15) 120.7(4) 1_555 1_555 1_555 yes
C(1) C(10) H(6) 119.1(8) 1_555 1_555 1_555 no
C(15) C(10) H(6) 120.1(8) 1_555 1_555 1_555 no
N(2) C(11) C(18) 99.8(4) 1_555 1_555 1_555 yes
N(2) C(11) H(12) 111.6(9) 1_555 1_555 1_555 no
N(2) C(11) H(13) 111.6(6) 1_555 1_555 1_555 no
C(18) C(11) H(12) 112.7(9) 1_555 1_555 1_555 no
C(18) C(11) H(13) 112(1) 1_555 1_555 1_555 no
H(12) C(11) H(13) 108(1) 1_555 1_555 1_555 no
F(2) C(12) F(3) 105.8(4) 1_555 1_555 1_555 yes
F(2) C(12) C(6) 119.2(4) 1_555 1_555 1_555 yes
F(2) C(12) C(18) 119.7(5) 1_555 1_555 1_555 yes
F(3) C(12) C(6) 112.0(4) 1_555 1_555 1_555 yes
F(3) C(12) C(18) 114.8(5) 1_555 1_555 1_555 yes
C(6) C(12) C(18) 84.7(3) 1_555 1_555 1_555 yes
C(14) C(13) C(15) 120.0(4) 1_555 1_555 1_555 yes
C(14) C(13) H(7) 119.3(9) 1_555 1_555 1_555 no
C(15) C(13) H(7) 120.7(9) 1_555 1_555 1_555 no
C(8) C(14) C(13) 120.1(4) 1_555 1_555 1_555 yes
C(8) C(14) H(8) 119.4(8) 1_555 1_555 1_555 no
C(13) C(14) H(8) 120.5(8) 1_555 1_555 1_555 no
C(10) C(15) C(13) 120.4(4) 1_555 1_555 1_555 yes
C(10) C(15) H(9) 119(1) 1_555 1_555 1_555 no
C(13) C(15) H(9) 119.6(10) 1_555 1_555 1_555 no
O(1) C(16) H(15) 109.5(5) 1_555 1_555 1_555 no
O(1) C(16) H(16) 109.5(5) 1_555 1_555 1_555 no
O(1) C(16) H(17) 109.1(6) 1_555 1_555 1_555 no
H(15) C(16) H(16) 110(1) 1_555 1_555 1_555 no
H(15) C(16) H(17) 108(1) 1_555 1_555 1_555 no
H(16) C(16) H(17) 109(1) 1_555 1_555 1_555 no
C(6) C(17) C(18) 81.8(4) 1_555 1_555 1_555 yes
C(6) C(17) H(10) 115.3(9) 1_555 1_555 1_555 no
C(6) C(17) H(11) 115.9(10) 1_555 1_555 1_555 no
C(18) C(17) H(10) 115.4(7) 1_555 1_555 1_555 no
C(18) C(17) H(11) 116.0(5) 1_555 1_555 1_555 no
H(10) C(17) H(11) 110(1) 1_555 1_555 1_555 no
C(11) C(18) C(12) 99.1(4) 1_555 1_555 1_555 yes
C(11) C(18) C(17) 101.7(4) 1_555 1_555 1_555 yes
C(11) C(18) H(14) 120(1) 1_555 1_555 1_555 no
C(12) C(18) C(17) 85.8(4) 1_555 1_555 1_555 yes
C(12) C(18) H(14) 121.4(10) 1_555 1_555 1_555 no
C(17) C(18) H(14) 121.5(9) 1_555 1_555 1_555 no
N(2) C(19) C(2) 118.2(3) 1_555 1_555 1_555 yes
N(2) C(19) C(4) 124.4(3) 1_555 1_555 1_555 yes
C(2) C(19) C(4) 117.4(3) 1_555 1_555 1_555 yes
#--------------------------------------------------------------------------=
#---
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
F(2) C(9) 3.351(5) 1_555 4_455 ?
F(2) C(2) 3.437(5) 1_555 4_455 ?
F(2) F(3) 3.594(7) 1_555 4_555 ?
F(3) C(8) 3.367(5) 1_555 4_454 ?
F(3) C(11) 3.584(5) 1_555 4_455 ?
O(1) C(10) 3.573(5) 1_555 1_655 ?
N(2) C(18) 3.540(6) 1_555 4_555 ?
C(4) C(13) 3.598(6) 1_555 2_554 ?
C(7) C(14) 3.563(6) 1_555 2_554 ?
#--------------------------------------------------------------------------=
#---
#Compound_6
#--------------------------------------------------------------------------=
#---
data_ene-2_(Compound_6)
_database_code_CSD               217316
#--------------------------------------------------------------------------=
# CHEMICAL DATA
_chemical_formula_sum            'C17 H27 F2 N O Si '
_chemical_formula_moiety         'C17 H27 F2 N O Si '
_chemical_formula_weight         327.49
_chemical_melting_point          ?
#--------------------------------------------------------------------------=
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,1/2-z
-x,-y,-z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-y,1/2+z
_cell_length_a                   36.849(7)
_cell_length_b                   6.5879(7)
_cell_length_c                   17.015(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.802(3)
_cell_angle_gamma                90
_cell_volume                     3686(1)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7121
_cell_measurement_theta_min      1.2
_cell_measurement_theta_max      27.5
_cell_measurement_temperature    290.2
#--------------------------------------------------------------------------=
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_size_rad          ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   none
#--------------------------------------------------------------------------=
# EXPERIMENTAL DATA
_diffrn_radiation_type           'Mo K=A5a'
_diffrn_radiation_wavelength     0.7107
_diffrn_measurement_device_type  'Rigaku RAXIS-IV Imaging Plate'
_diffrn_measurement_method       =A5w
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4283
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_theta_max         27.48
_diffrn_measured_fraction_theta_max 0.9308
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.9308
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
#--------------------------------------------------------------------------=
#---
# REFINEMENT DATA=20
_refine_special_details          
;
Refinement using reflections with F^2^ > 5.0 sigma(F^2^). The weighted
R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with
F set to zero for negative F. The threshold expression of
F^2^ > 5.0 sigma(F^2^) is used only for calculating R-factor (gt).
;
_reflns_number_total             3944
_reflns_number_gt                2464
_reflns_threshold_expression     F^2^>5.0=A5s(F^2^)
_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0702
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_reflns         2464
_refine_ls_number_parameters     199
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w == 1/[=A5s^2^(Fo) + 0.00422|Fo|^2^]'
_refine_ls_shift/su_max          0.0034
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
F F 0.017 0.010
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
Si Si 0.082 0.070
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
#--------------------------------------------------------------------------=
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS=20
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si(1) Si 0.60880(2) -0.14671(8) 0.32281(4) 0.0486(2) Uani 1.00 d . . .
F(2) F 0.69180(4) -0.2900(2) 0.3599(1) 0.0686(4) Uani 1.00 d . . .
F(3) F 0.69385(5) -0.2205(2) 0.2376(1) 0.0709(5) Uani 1.00 d . . .
O(1) O 0.51801(8) 0.3865(3) -0.1033(1) 0.0956(7) Uani 1.00 d . . .
N(1) N 0.63473(5) 0.1151(2) 0.2249(1) 0.0476(5) Uani 1.00 d . . .
C(1) C 0.68161(7) -0.1404(3) 0.2970(2) 0.0501(6) Uani 1.00 d . . .
C(2) C 0.70304(6) 0.0576(3) 0.3330(1) 0.0484(6) Uani 1.00 d . . .
C(3) C 0.60613(7) 0.1812(3) 0.1423(1) 0.0478(6) Uani 1.00 d . . .
C(4) C 0.63650(6) -0.0989(3) 0.2520(1) 0.0449(5) Uani 1.00 d . . .
C(5) C 0.67512(8) 0.2056(3) 0.2632(2) 0.0563(6) Uani 1.00 d . . .
C(6) C 0.57353(7) 0.0613(3) 0.0851(1) 0.0541(6) Uani 1.00 d . . .
C(7) C 0.60888(8) 0.3767(3) 0.1136(2) 0.0605(7) Uani 1.00 d . . .
C(8) C 0.54526(8) 0.1349(4) 0.0044(2) 0.0619(7) Uani 1.00 d . . .
C(9) C 0.54790(8) 0.3278(4) -0.0214(2) 0.0646(7) Uani 1.00 d . . .
C(10) C 0.57981(9) 0.4496(3) 0.0328(2) 0.0672(8) Uani 1.00 d . . .
C(11) C 0.74788(7) 0.0746(4) 0.3534(2) 0.0597(7) Uani 1.00 d . . .
C(12) C 0.63579(8) -0.0235(4) 0.4319(2) 0.0664(8) Uani 1.00 d . . .
C(13) C 0.55733(8) -0.0347(5) 0.2661(2) 0.0722(8) Uani 1.00 d . . .
C(15) C 0.76325(8) 0.2890(5) 0.3867(2) 0.0736(9) Uani 1.00 d . . .
C(16) C 0.60556(9) -0.4263(4) 0.3343(2) 0.0765(9) Uani 1.00 d . . .
C(17) C 0.77438(9) -0.0845(6) 0.4179(2) 0.091(1) Uani 1.00 d . . .
C(18) C 0.5104(1) 0.5899(6) -0.1204(2) 0.102(1) Uani 1.00 d . . .
H(1) H 0.5707 -0.0729 0.1021 0.0650 Uiso 1.00 calc . . .
H(2) H 0.6309 0.4616 0.1499 0.0724 Uiso 1.00 calc . . .
H(3) H 0.5237 0.0494 -0.0336 0.0742 Uiso 1.00 calc . . .
H(4) H 0.5821 0.5838 0.0150 0.0807 Uiso 1.00 calc . . .
H(5) H 0.7012 0.0853 0.3859 0.0580 Uiso 1.00 calc . . .
H(6) H 0.6244 -0.1808 0.2006 0.0539 Uiso 1.00 calc . . .
H(7) H 0.7496 0.0555 0.2998 0.0717 Uiso 1.00 calc . . .
H(8) H 0.6840 0.2242 0.2192 0.0676 Uiso 1.00 calc . . .
H(9) H 0.6748 0.3328 0.2892 0.0676 Uiso 1.00 calc . . .
H(10) H 0.6624 -0.0778 0.4620 0.0796 Uiso 1.00 calc . . .
H(11) H 0.6373 0.1186 0.4242 0.0796 Uiso 1.00 calc . . .
H(12) H 0.6213 -0.0479 0.4652 0.0796 Uiso 1.00 calc . . .
H(13) H 0.5595 0.1069 0.2588 0.0866 Uiso 1.00 calc . . .
H(14) H 0.5429 -0.0967 0.2099 0.0866 Uiso 1.00 calc . . .
H(15) H 0.5432 -0.0573 0.3002 0.0866 Uiso 1.00 calc . . .
H(16) H 0.7906 0.3023 0.3963 0.0886 Uiso 1.00 calc . . .
H(17) H 0.7468 0.3858 0.3441 0.0886 Uiso 1.00 calc . . .
H(18) H 0.7619 0.3123 0.4404 0.0886 Uiso 1.00 calc . . .
H(19) H 0.5920 -0.4542 0.3691 0.0918 Uiso 1.00 calc . . .
H(20) H 0.5908 -0.4854 0.2776 0.0918 Uiso 1.00 calc . . .
H(21) H 0.6322 -0.4820 0.3618 0.0918 Uiso 1.00 calc . . .
H(22) H 0.7647 -0.2160 0.3949 0.1095 Uiso 1.00 calc . . .
H(23) H 0.8016 -0.0699 0.4267 0.1095 Uiso 1.00 calc . . .
H(24) H 0.7735 -0.0681 0.4724 0.1095 Uiso 1.00 calc . . .
H(25) H 0.5344 0.6558 -0.1145 0.1221 Uiso 1.00 calc . . .
H(26) H 0.4894 0.6074 -0.1787 0.1221 Uiso 1.00 calc . . .
H(27) H 0.5020 0.6465 -0.0799 0.1221 Uiso 1.00 calc . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Si(1) 0.0480(3) 0.0492(3) 0.0544(4) -0.0009(2) 0.0282(3) 0.0031(2)
F(2) 0.0598(9) 0.0622(8) 0.0837(10) 0.0104(6) 0.0323(8) 0.0246(7)
F(3) 0.0709(10) 0.0732(8) 0.089(1) -0.0035(7) 0.0535(9) -0.0221(8)
O(1) 0.109(2) 0.089(1) 0.061(1) 0.020(1) 0.013(1) 0.010(1)
N(1) 0.052(1) 0.0420(8) 0.0457(10) -0.0022(6) 0.0196(8) 0.0038(7)
C(1) 0.056(1) 0.051(1) 0.055(1) 0.0051(9) 0.035(1) 0.0055(9)
C(2) 0.047(1) 0.059(1) 0.043(1) -0.0017(9) 0.0240(9) -0.0009(9)
C(3) 0.058(1) 0.0479(10) 0.043(1) 0.0012(8) 0.0268(10) -0.0001(8)
C(4) 0.049(1) 0.0420(9) 0.044(1) -0.0012(7) 0.0219(9) -0.0007(8)
C(5) 0.057(1) 0.051(1) 0.058(1) -0.0076(9) 0.023(1) 0.0003(9)
C(6) 0.054(1) 0.059(1) 0.049(1) -0.0046(9) 0.023(1) -0.0016(9)
C(7) 0.078(2) 0.050(1) 0.050(1) 0.0004(10) 0.026(1) -0.0015(9)
C(8) 0.059(1) 0.072(1) 0.052(1) -0.004(1) 0.023(1) -0.004(1)
C(9) 0.069(2) 0.073(1) 0.047(1) 0.017(1) 0.021(1) 0.001(1)
C(10) 0.096(2) 0.050(1) 0.059(1) 0.010(1) 0.038(1) 0.010(1)
C(11) 0.051(1) 0.082(1) 0.053(1) -0.007(1) 0.029(1) -0.003(1)
C(12) 0.064(2) 0.082(2) 0.061(2) -0.002(1) 0.035(1) -0.002(1)
C(13) 0.054(1) 0.095(2) 0.072(2) 0.007(1) 0.032(1) 0.007(1)
C(15) 0.060(2) 0.101(2) 0.063(2) -0.025(1) 0.031(1) -0.015(1)
C(16) 0.091(2) 0.061(1) 0.099(2) -0.010(1) 0.063(2) 0.005(1)
C(17) 0.049(2) 0.112(2) 0.103(2) 0.007(1) 0.027(2) 0.014(2)
C(18) 0.117(3) 0.105(2) 0.087(2) 0.045(2) 0.049(2) 0.034(2)
#--------------------------------------------------------------------------=
#---
_computing_data_collection       PROCESS
_computing_cell_refinement       PROCESS
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_structure_solution    SIR97
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_molecular_graphics    ?
#--------------------------------------------------------------------------=
#---
_geom_special_details            
;
?
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si(1) C(4) 1.924(2) . . yes
Si(1) C(12) 1.852(3) . . yes
Si(1) C(13) 1.850(3) . . yes
Si(1) C(16) 1.862(3) . . yes
F(2) C(1) 1.377(2) . . yes
F(3) C(1) 1.383(3) . . yes
O(1) C(9) 1.385(3) . . yes
O(1) C(18) 1.373(4) . . yes
N(1) C(3) 1.393(3) . . yes
N(1) C(4) 1.476(2) . . yes
N(1) C(5) 1.456(3) . . yes
C(1) C(2) 1.505(3) . . yes
C(1) C(4) 1.509(3) . . yes
C(2) C(5) 1.523(3) . . yes
C(2) C(11) 1.531(3) . . yes
C(3) C(6) 1.400(3) . . yes
C(3) C(7) 1.397(3) . . yes
C(6) C(8) 1.385(3) . . yes
C(7) C(10) 1.393(3) . . yes
C(8) C(9) 1.362(4) . . yes
C(9) C(10) 1.378(4) . . yes
C(11) C(15) 1.532(4) . . yes
C(11) C(17) 1.513(4) . . yes
#--------------------------------------------------------------------------=
#---
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(4) Si(1) C(12) 111.1(1) . . . yes
C(4) Si(1) C(13) 108.5(1) . . . yes
C(4) Si(1) C(16) 107.8(1) . . . yes
C(12) Si(1) C(13) 108.0(1) . . . yes
C(12) Si(1) C(16) 111.0(1) . . . yes
C(13) Si(1) C(16) 110.5(1) . . . yes
C(9) O(1) C(18) 118.6(3) . . . yes
C(3) N(1) C(4) 121.4(2) . . . yes
C(3) N(1) C(5) 118.6(2) . . . yes
C(4) N(1) C(5) 111.1(2) . . . yes
F(2) C(1) F(3) 103.3(2) . . . yes
F(2) C(1) C(2) 113.3(2) . . . yes
F(2) C(1) C(4) 112.1(2) . . . yes
F(3) C(1) C(2) 110.1(2) . . . yes
F(3) C(1) C(4) 110.3(2) . . . yes
C(2) C(1) C(4) 107.8(2) . . . yes
C(1) C(2) C(5) 101.0(2) . . . yes
C(1) C(2) C(11) 118.0(2) . . . yes
C(5) C(2) C(11) 114.2(2) . . . yes
N(1) C(3) C(6) 123.1(2) . . . yes
N(1) C(3) C(7) 120.0(2) . . . yes
C(6) C(3) C(7) 116.9(2) . . . yes
Si(1) C(4) N(1) 113.0(1) . . . yes
Si(1) C(4) C(1) 115.3(1) . . . yes
N(1) C(4) C(1) 102.4(2) . . . yes
N(1) C(5) C(2) 106.4(2) . . . yes
C(3) C(6) C(8) 121.2(2) . . . yes
C(3) C(7) C(10) 121.2(2) . . . yes
C(6) C(8) C(9) 121.0(2) . . . yes
O(1) C(9) C(8) 116.4(2) . . . yes
O(1) C(9) C(10) 124.2(3) . . . yes
C(8) C(9) C(10) 119.4(2) . . . yes
C(7) C(10) C(9) 120.3(2) . . . yes
C(2) C(11) C(15) 109.4(2) . . . yes
C(2) C(11) C(17) 113.0(2) . . . yes
C(15) C(11) C(17) 111.1(2) . . . yes
#--------------------------------------------------------------------------=
#---
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Si(1) C(4) N(1) C(3) -97.8(2) . . . . yes
Si(1) C(4) N(1) C(5) 115.6(2) . . . . yes
Si(1) C(4) C(1) F(2) 29.5(2) . . . . yes
Si(1) C(4) C(1) F(3) 144.0(1) . . . . yes
Si(1) C(4) C(1) C(2) -95.7(2) . . . . yes
F(2) C(1) C(2) C(5) -158.8(2) . . . . yes
F(2) C(1) C(2) C(11) 75.9(2) . . . . yes
F(2) C(1) C(4) N(1) 152.7(2) . . . . yes
F(3) C(1) C(2) C(5) 86.0(2) . . . . yes
F(3) C(1) C(2) C(11) -39.2(3) . . . . yes
F(3) C(1) C(4) N(1) -92.8(2) . . . . yes
O(1) C(9) C(8) C(6) -179.8(2) . . . . yes
O(1) C(9) C(10) C(7) -179.0(3) . . . . yes
N(1) C(3) C(6) C(8) 178.5(2) . . . . yes
N(1) C(3) C(7) C(10) -177.4(2) . . . . yes
N(1) C(4) Si(1) C(12) -68.3(2) . . . . yes
N(1) C(4) Si(1) C(13) 50.2(2) . . . . yes
N(1) C(4) Si(1) C(16) 169.9(2) . . . . yes
N(1) C(4) C(1) C(2) 27.4(2) . . . . yes
N(1) C(5) C(2) C(1) 27.8(2) . . . . yes
N(1) C(5) C(2) C(11) 155.6(2) . . . . yes
C(1) C(2) C(11) C(15) 178.5(2) . . . . yes
C(1) C(2) C(11) C(17) -57.1(3) . . . . yes
C(1) C(4) Si(1) C(12) 49.0(2) . . . . yes
C(1) C(4) Si(1) C(13) 167.6(2) . . . . yes
C(1) C(4) Si(1) C(16) -72.8(2) . . . . yes
C(1) C(4) N(1) C(3) 137.6(2) . . . . yes
C(1) C(4) N(1) C(5) -9.1(2) . . . . yes
C(2) C(5) N(1) C(3) -159.7(2) . . . . yes
C(2) C(5) N(1) C(4) -12.1(2) . . . . yes
C(3) C(6) C(8) C(9) -1.1(4) . . . . yes
C(3) C(7) C(10) C(9) -1.1(4) . . . . yes
C(4) N(1) C(3) C(6) 10.3(3) . . . . yes
C(4) N(1) C(3) C(7) -170.7(2) . . . . yes
C(4) C(1) C(2) C(5) -34.3(2) . . . . yes
C(4) C(1) C(2) C(11) -159.6(2) . . . . yes
C(5) N(1) C(3) C(6) 154.6(2) . . . . yes
C(5) N(1) C(3) C(7) -26.5(3) . . . . yes
C(5) C(2) C(11) C(15) 59.9(3) . . . . yes
C(5) C(2) C(11) C(17) -175.6(2) . . . . yes
C(6) C(3) C(7) C(10) 1.6(4) . . . . yes
C(6) C(8) C(9) C(10) 1.7(4) . . . . yes
C(7) C(3) C(6) C(8) -0.5(4) . . . . yes
C(7) C(10) C(9) C(8) -0.6(4) . . . . yes
C(8) C(9) O(1) C(18) 157.9(3) . . . . yes
C(10) C(9) O(1) C(18) -23.7(5) . . . . yes
C(10) C(9) O(1) C(18) -23.7(5) . . . . yes
#--------------------------------------------------------------------------=
#---
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
F(2) C(17) 3.505(4) . 7_646 ?
F(3) C(15) 3.162(3) . 6_645 ?
F(3) C(11) 3.440(3) . 6_645 ?
#--------------------------------------------------------------------------=
#---
#--------------------------------------------------------------------------=
#---