#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/49/7204971.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_7204971
loop_
_publ_author_name
'Peng, Weimin'
'Zhu, Shizheng'
_publ_section_title
;
 Reactions of N-benzyl-pyridinium or -isoquinolinium ylides with ethyl
 3-fluoro-3-(fluoroalkyl)acrylates to give fluoroalkyl-substituted
 indolizine and pyrrolo[2,1-a]isoquinoline derivatives
;
_journal_issue                   23
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              3204
_journal_paper_doi               10.1039/b103586j
_journal_year                    2001
_chemical_formula_sum            'C22 H16 F N O3'
_chemical_formula_weight         361.36
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 103.550(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.375(4)
_cell_length_b                   11.151(2)
_cell_length_c                   16.522(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      5.0
_cell_volume                     3649.3(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.475
_diffrn_measured_fraction_theta_max 0.475
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       theta/2theta
_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  0.0473
_diffrn_reflns_av_sigmaI/netI    0.1319
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5026
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        no
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.133
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.2076
_refine_ls_R_factor_gt           0.0652
_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)+(0.0508P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1502
_reflns_number_gt                1565
_reflns_number_total             4199
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b103586j.txt
_cod_data_source_block           C22H16FNO3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      C2/C
_cod_database_code               7204971
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
C1 C 0.20206(15) 0.4037(3) 0.15497(17) 0.0435(8) Uani 1 d . . .
C2 C 0.14867(14) 0.4867(3) 0.13400(17) 0.0468(8) Uani 1 d . . .
C3 C 0.15137(14) 0.5422(3) 0.05982(18) 0.0473(8) Uani 1 d . . .
N N 0.20523(12) 0.4927(2) 0.03525(14) 0.0450(6) Uani 1 d . . .
C4 C 0.22744(17) 0.5179(3) -0.0372(2) 0.0538(9) Uani 1 d . . .
C5 C 0.28123(17) 0.4612(3) -0.0509(2) 0.0551(9) Uani 1 d . . .
C6 C 0.31802(16) 0.3752(3) 0.00611(18) 0.0484(8) Uani 1 d . . .
C7 C 0.37599(18) 0.3201(3) -0.0074(2) 0.0580(9) Uani 1 d . . .
C8 C 0.41333(19) 0.2423(3) 0.0496(2) 0.0618(10) Uani 1 d . . .
C9 C 0.3930(2) 0.2168(3) 0.1218(2) 0.0650(11) Uani 1 d . . .
C10 C 0.33516(18) 0.2686(3) 0.1368(2) 0.0572(10) Uani 1 d . . .
C11 C 0.29697(15) 0.3485(3) 0.07950(18) 0.0458(8) Uani 1 d . . .
C12 C 0.23746(14) 0.4079(3) 0.09364(17) 0.0428(8) Uani 1 d . . .
C13 C 0.21449(17) 0.3246(3) 0.22923(19) 0.0509(8) Uani 1 d . . .
O1 O 0.25855(12) 0.3388(2) 0.29059(13) 0.0813(8) Uani 1 d . . .
O2 O 0.17019(11) 0.2359(2) 0.21980(12) 0.0598(7) Uani 1 d . . .
C14 C 0.1727(2) 0.1580(4) 0.2915(2) 0.0761(12) Uani 1 d . . .
C15 C 0.1192(3) 0.0669(5) 0.2653(3) 0.0864(14) Uani 1 d . . .
C16 C 0.10211(17) 0.5111(3) 0.1850(2) 0.0620(10) Uani 1 d . . .
O3 O 0.10633(12) 0.4656(2) 0.25364(14) 0.0782(8) Uani 1 d . . .
F F 0.05314(11) 0.5858(2) 0.15687(13) 0.0971(8) Uani 1 d . . .
C17 C 0.11036(15) 0.6394(3) 0.01144(19) 0.0486(8) Uani 1 d . . .
C18 C 0.1149(2) 0.7542(4) 0.0426(3) 0.0737(11) Uani 1 d . . .
C19 C 0.0766(2) 0.8455(4) -0.0010(3) 0.0842(13) Uani 1 d . . .
C20 C 0.0342(2) 0.8247(4) -0.0764(3) 0.0715(11) Uani 1 d . . .
C21 C 0.0292(2) 0.7110(4) -0.1072(2) 0.0734(12) Uani 1 d . . .
C22 C 0.06733(19) 0.6193(4) -0.0640(2) 0.0632(10) Uani 1 d . . .
H4 H 0.2019(15) 0.583(3) -0.0705(17) 0.068(10) Uiso 1 d . . .
H5 H 0.3004(13) 0.478(2) -0.1009(17) 0.055(9) Uiso 1 d . . .
H7 H 0.3895(14) 0.340(3) -0.0576(17) 0.055(9) Uiso 1 d . . .
H8 H 0.4539(16) 0.206(3) 0.0410(17) 0.062(10) Uiso 1 d . . .
H9 H 0.4193(18) 0.172(3) 0.160(2) 0.091(14) Uiso 1 d . . .
H10 H 0.3247(15) 0.251(3) 0.189(2) 0.064(10) Uiso 1 d . . .
H14A H 0.1633(19) 0.220(3) 0.342(2) 0.108(14) Uiso 1 d . . .
H14B H 0.2188(19) 0.126(3) 0.306(2) 0.096(14) Uiso 1 d . . .
H15A H 0.076(2) 0.105(4) 0.242(2) 0.111(16) Uiso 1 d . . .
H15B H 0.122(2) 0.011(4) 0.217(3) 0.133(19) Uiso 1 d . . .
H15C H 0.1160(17) 0.012(3) 0.314(2) 0.094(12) Uiso 1 d . . .
H18 H 0.1434(18) 0.763(3) 0.098(2) 0.081(11) Uiso 1 d . . .
H19 H 0.081(2) 0.926(4) 0.018(2) 0.113(16) Uiso 1 d . . .
H20 H 0.007(2) 0.891(3) -0.107(2) 0.111(15) Uiso 1 d . . .
H21 H 0.0028(19) 0.689(3) -0.159(2) 0.101(14) Uiso 1 d . . .
H22 H 0.0632(12) 0.544(2) -0.0891(15) 0.039(8) Uiso 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C1 C2 107.7(2) . . ?
C12 C1 C13 127.8(3) . . ?
C2 C1 C13 124.5(3) . . ?
C3 C2 C1 108.8(3) . . ?
C3 C2 C16 127.1(3) . . ?
C1 C2 C16 124.0(3) . . ?
N C3 C2 106.4(3) . . ?
N C3 C17 121.6(3) . . ?
C2 C3 C17 132.0(3) . . ?
C3 N C12 110.3(2) . . ?
C3 N C4 127.7(3) . . ?
C12 N C4 122.0(3) . . ?
C5 C4 N 119.5(3) . . ?
C5 C4 H4 127.2(18) . . ?
N C4 H4 113.0(18) . . ?
C4 C5 C6 122.2(3) . . ?
C4 C5 H5 122.6(15) . . ?
C6 C5 H5 115.1(15) . . ?
C7 C6 C11 118.9(3) . . ?
C7 C6 C5 121.6(3) . . ?
C11 C6 C5 119.4(3) . . ?
C8 C7 C6 121.6(3) . . ?
C8 C7 H7 120.8(17) . . ?
C6 C7 H7 117.6(17) . . ?
C7 C8 C9 119.5(4) . . ?
C7 C8 H8 121.6(18) . . ?
C9 C8 H8 118.9(18) . . ?
C8 C9 C10 120.5(4) . . ?
C8 C9 H9 118(2) . . ?
C10 C9 H9 121(2) . . ?
C9 C10 C11 120.4(4) . . ?
C9 C10 H10 117.1(18) . . ?
C11 C10 H10 122.3(18) . . ?
C10 C11 C6 119.0(3) . . ?
C10 C11 C12 122.5(3) . . ?
C6 C11 C12 118.5(3) . . ?
C1 C12 N 106.8(2) . . ?
C1 C12 C11 134.9(3) . . ?
N C12 C11 118.3(3) . . ?
O1 C13 O2 123.6(3) . . ?
O1 C13 C1 124.8(3) . . ?
O2 C13 C1 111.5(3) . . ?
C13 O2 C14 117.1(3) . . ?
O2 C14 C15 106.7(3) . . ?
O2 C14 H14A 104.9(18) . . ?
C15 C14 H14A 113.2(19) . . ?
O2 C14 H14B 106(2) . . ?
C15 C14 H14B 115(2) . . ?
H14A C14 H14B 111(3) . . ?
C14 C15 H15A 111(2) . . ?
C14 C15 H15B 118(3) . . ?
H15A C15 H15B 99(3) . . ?
C14 C15 H15C 110.8(19) . . ?
H15A C15 H15C 111(3) . . ?
H15B C15 H15C 106(3) . . ?
O3 C16 F 118.5(3) . . ?
O3 C16 C2 123.5(3) . . ?
F C16 C2 118.0(3) . . ?
C22 C17 C18 117.9(3) . . ?
C22 C17 C3 122.2(3) . . ?
C18 C17 C3 119.9(3) . . ?
C17 C18 C19 120.8(4) . . ?
C17 C18 H18 115(2) . . ?
C19 C18 H18 124(2) . . ?
C20 C19 C18 120.8(4) . . ?
C20 C19 H19 117(2) . . ?
C18 C19 H19 122(2) . . ?
C19 C20 C21 118.6(4) . . ?
C19 C20 H20 120(2) . . ?
C21 C20 H20 122(2) . . ?
C20 C21 C22 120.9(4) . . ?
C20 C21 H21 124(2) . . ?
C22 C21 H21 115(2) . . ?
C17 C22 C21 121.0(4) . . ?
C17 C22 H22 121.8(16) . . ?
C21 C22 H22 117.2(16) . . ?
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 C12 1.375(4) . ?
C1 C2 1.409(4) . ?
C1 C13 1.483(4) . ?
C2 C3 1.385(4) . ?
C2 C16 1.435(4) . ?
C3 N 1.372(4) . ?
C3 C17 1.483(4) . ?
N C12 1.399(3) . ?
N C4 1.404(4) . ?
C4 C5 1.330(4) . ?
C4 H4 0.98(3) . ?
C5 C6 1.428(4) . ?
C5 H5 1.01(3) . ?
C6 C7 1.395(4) . ?
C6 C11 1.410(4) . ?
C7 C8 1.371(5) . ?
C7 H7 0.96(3) . ?
C8 C9 1.381(5) . ?
C8 H8 0.96(3) . ?
C9 C10 1.386(5) . ?
C9 H9 0.88(3) . ?
C10 C11 1.396(4) . ?
C10 H10 0.96(3) . ?
C11 C12 1.448(4) . ?
C13 O1 1.197(3) . ?
C13 O2 1.324(4) . ?
O2 C14 1.461(4) . ?
C14 C15 1.479(6) . ?
C14 H14A 1.14(4) . ?
C14 H14B 0.98(4) . ?
C15 H15A 0.97(4) . ?
C15 H15B 1.03(4) . ?
C15 H15C 1.02(3) . ?
C16 O3 1.226(4) . ?
C16 F 1.300(4) . ?
C17 C22 1.364(4) . ?
C17 C18 1.374(4) . ?
C18 C19 1.378(5) . ?
C18 H18 0.96(3) . ?
C19 C20 1.359(5) . ?
C19 H19 0.95(4) . ?
C20 C21 1.361(5) . ?
C20 H20 0.99(4) . ?
C21 C22 1.378(5) . ?
C21 H21 0.93(4) . ?
C22 H22 0.93(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4401277
