#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/29/1502910.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_1502910
loop_
_publ_author_name
'Oura, Ichiro'
'Shimizu, Kenta'
'Ogata, Kenichi'
'Fukuzawa, Shin-Ichi'
_publ_section_title
;
 Highly endo-selective and enantioselective 1,3-dipolar cycloaddition of
 azomethine ylide with alpha-enones catalyzed by a
 silver(I)/ThioClickFerrophos complex.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1752
_journal_page_last               1755
_journal_paper_doi               10.1021/ol100336q
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C20 H20 Cl N O3 '
_chemical_formula_sum            'C20 H20 Cl N O3'
_chemical_formula_weight         357.84
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   8.817(2)
_cell_length_b                   9.476(2)
_cell_length_c                   21.330(5)
_cell_measurement_reflns_used    5192
_cell_measurement_temperature    123.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     1782.1(7)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR97
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.066
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13715
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             752.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.24
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1712 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4046
_refine_ls_R_factor_gt           0.0442
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0439P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                3524
_reflns_number_total             4046
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ol100336q_si_003.cif
_cod_data_source_block           '__20090915_Ohura_Ex634prod'
_cod_original_formula_sum        'C20 H20 Cl N O3 '
_cod_database_code               1502910
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-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
Cl(1) Cl 0.11561(9) 0.22567(7) 0.46296(2) 0.04744(18) Uani 1.00 1 d .
O(1) O -0.12075(18) 0.11019(16) 0.79225(6) 0.0354(3) Uani 1.00 1 d .
O(2) O -0.09480(17) -0.02811(16) 0.87667(6) 0.0291(3) Uani 1.00 1 d .
O(3) O 0.4003(2) 0.28526(16) 0.71926(6) 0.0335(3) Uani 1.00 1 d .
N(1) N 0.1173(2) -0.08621(18) 0.74804(7) 0.0273(3) Uani 1.00 1 d .
C(1) C 0.1162(2) -0.0123(2) 0.80827(8) 0.0232(4) Uani 1.00 1 d .
C(2) C 0.2178(2) 0.1168(2) 0.79729(7) 0.0215(3) Uani 1.00 1 d .
C(3) C 0.3425(2) 0.0531(2) 0.75586(8) 0.0228(4) Uani 1.00 1 d .
C(4) C 0.2549(2) -0.0493(2) 0.71176(8) 0.0249(4) Uani 1.00 1 d .
C(5) C -0.0452(2) 0.0318(2) 0.82384(8) 0.0254(4) Uani 1.00 1 d .
C(6) C -0.2532(2) -0.0030(2) 0.89120(9) 0.0363(5) Uani 1.00 1 d .
C(7) C 0.2687(2) 0.1891(2) 0.85681(7) 0.0221(4) Uani 1.00 1 d .
C(8) C 0.2065(2) 0.3172(2) 0.87420(8) 0.0286(4) Uani 1.00 1 d .
C(9) C 0.2513(2) 0.3833(2) 0.92974(8) 0.0352(5) Uani 1.00 1 d .
C(10) C 0.3588(2) 0.3208(2) 0.96785(8) 0.0338(5) Uani 1.00 1 d .
C(11) C 0.4194(2) 0.1922(2) 0.95175(8) 0.0357(5) Uani 1.00 1 d .
C(12) C 0.3745(2) 0.1267(2) 0.89648(8) 0.0292(4) Uani 1.00 1 d .
C(13) C 0.4390(2) 0.1621(2) 0.72275(8) 0.0253(4) Uani 1.00 1 d .
C(14) C 0.5877(2) 0.1125(2) 0.69695(8) 0.0344(5) Uani 1.00 1 d .
C(15) C 0.2126(2) 0.0145(2) 0.64849(8) 0.0259(4) Uani 1.00 1 d .
C(16) C 0.3068(2) -0.0085(2) 0.59725(8) 0.0315(4) Uani 1.00 1 d .
C(17) C 0.2773(2) 0.0549(2) 0.53964(9) 0.0362(5) Uani 1.00 1 d .
C(18) C 0.1526(2) 0.1407(2) 0.53438(9) 0.0327(5) Uani 1.00 1 d .
C(19) C 0.0533(2) 0.1614(2) 0.58346(9) 0.0308(4) Uani 1.00 1 d .
C(20) C 0.0843(2) 0.0975(2) 0.64074(8) 0.0265(4) Uani 1.00 1 d .
H(1) H 0.1100 -0.1815 0.7532 0.040 Uiso 1.00 1 c R
H(2) H 0.1589 -0.0736 0.8421 0.028 Uiso 1.00 1 c R
H(3) H 0.1596 0.1866 0.7716 0.026 Uiso 1.00 1 c R
H(4) H 0.4105 -0.0046 0.7832 0.027 Uiso 1.00 1 c R
H(5) H 0.3170 -0.1363 0.7049 0.030 Uiso 1.00 1 c R
H(6) H -0.3170 -0.0470 0.8591 0.044 Uiso 1.00 1 c R
H(7) H -0.2726 0.0989 0.8921 0.044 Uiso 1.00 1 c R
H(8) H -0.2772 -0.0437 0.9323 0.044 Uiso 1.00 1 c R
H(9) H 0.1326 0.3606 0.8482 0.034 Uiso 1.00 1 c R
H(10) H 0.2079 0.4713 0.9413 0.042 Uiso 1.00 1 c R
H(11) H 0.3908 0.3667 1.0052 0.041 Uiso 1.00 1 c R
H(12) H 0.4919 0.1482 0.9783 0.043 Uiso 1.00 1 c R
H(13) H 0.4167 0.0377 0.8856 0.035 Uiso 1.00 1 c R
H(14) H 0.6665 0.1227 0.7290 0.041 Uiso 1.00 1 c R
H(15) H 0.6146 0.1693 0.6602 0.041 Uiso 1.00 1 c R
H(16) H 0.5793 0.0131 0.6847 0.041 Uiso 1.00 1 c R
H(17) H 0.3926 -0.0684 0.6016 0.038 Uiso 1.00 1 c R
H(18) H 0.3421 0.0392 0.5048 0.043 Uiso 1.00 1 c R
H(19) H -0.0345 0.2182 0.5783 0.037 Uiso 1.00 1 c R
H(20) H 0.0169 0.1109 0.6750 0.032 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
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)
;
Cl Cl 0.148 0.159
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
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
_geom_angle_publ_flag
C(5) O(2) C(6) 115.21(15) yes
C(1) N(1) C(4) 110.57(15) yes
N(1) C(1) C(2) 104.10(14) yes
N(1) C(1) C(5) 109.24(15) yes
C(2) C(1) C(5) 111.12(15) yes
C(1) C(2) C(3) 101.12(15) yes
C(1) C(2) C(7) 114.02(13) yes
C(3) C(2) C(7) 116.67(15) yes
C(2) C(3) C(4) 103.73(15) yes
C(2) C(3) C(13) 113.82(16) yes
C(4) C(3) C(13) 114.99(14) yes
N(1) C(4) C(3) 103.76(13) yes
N(1) C(4) C(15) 110.83(16) yes
C(3) C(4) C(15) 114.11(16) yes
O(1) C(5) O(2) 123.58(19) yes
O(1) C(5) C(1) 124.44(16) yes
O(2) C(5) C(1) 111.97(16) yes
C(2) C(7) C(8) 120.36(16) yes
C(2) C(7) C(12) 121.16(17) yes
C(8) C(7) C(12) 118.44(16) yes
C(7) C(8) C(9) 120.57(19) yes
C(8) C(9) C(10) 120.1(2) yes
C(9) C(10) C(11) 119.98(18) yes
C(10) C(11) C(12) 119.83(19) yes
C(7) C(12) C(11) 121.1(2) yes
O(3) C(13) C(3) 121.65(18) yes
O(3) C(13) C(14) 121.56(19) yes
C(3) C(13) C(14) 116.74(18) yes
C(4) C(15) C(16) 119.15(18) yes
C(4) C(15) C(20) 121.99(16) yes
C(16) C(15) C(20) 118.85(17) yes
C(15) C(16) C(17) 120.9(2) yes
C(16) C(17) C(18) 118.53(19) yes
Cl(1) C(18) C(17) 119.48(16) yes
Cl(1) C(18) C(19) 118.42(17) yes
C(17) C(18) C(19) 122.09(18) yes
C(18) C(19) C(20) 118.7(2) yes
C(15) C(20) C(19) 120.78(18) yes
C(1) N(1) H(1) 111.5 no
C(4) N(1) H(1) 110.8 no
N(1) C(1) H(2) 110.7 no
C(2) C(1) H(2) 110.7 no
C(5) C(1) H(2) 110.7 no
C(1) C(2) H(3) 108.2 no
C(3) C(2) H(3) 108.2 no
C(7) C(2) H(3) 108.2 no
C(2) C(3) H(4) 108.0 no
C(4) C(3) H(4) 108.0 no
C(13) C(3) H(4) 108.0 no
N(1) C(4) H(5) 109.3 no
C(3) C(4) H(5) 109.3 no
C(15) C(4) H(5) 109.3 no
O(2) C(6) H(6) 109.5 no
O(2) C(6) H(7) 109.5 no
O(2) C(6) H(8) 109.5 no
H(6) C(6) H(7) 109.5 no
H(6) C(6) H(8) 109.5 no
H(7) C(6) H(8) 109.5 no
C(7) C(8) H(9) 119.7 no
C(9) C(8) H(9) 119.7 no
C(8) C(9) H(10) 120.0 no
C(10) C(9) H(10) 120.0 no
C(9) C(10) H(11) 120.0 no
C(11) C(10) H(11) 120.0 no
C(10) C(11) H(12) 120.1 no
C(12) C(11) H(12) 120.1 no
C(7) C(12) H(13) 119.5 no
C(11) C(12) H(13) 119.4 no
C(13) C(14) H(14) 109.5 no
C(13) C(14) H(15) 109.5 no
C(13) C(14) H(16) 109.5 no
H(14) C(14) H(15) 109.5 no
H(14) C(14) H(16) 109.5 no
H(15) C(14) H(16) 109.5 no
C(15) C(16) H(17) 119.5 no
C(17) C(16) H(17) 119.5 no
C(16) C(17) H(18) 120.7 no
C(18) C(17) H(18) 120.7 no
C(18) C(19) H(19) 120.6 no
C(20) C(19) H(19) 120.6 no
C(15) C(20) H(20) 119.6 no
C(19) C(20) H(20) 119.6 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl(1) C(18) 1.754(2) yes
O(1) C(5) 1.204(2) yes
O(2) C(5) 1.335(2) yes
O(2) C(6) 1.451(2) yes
O(3) C(13) 1.218(2) yes
N(1) C(1) 1.463(2) yes
N(1) C(4) 1.481(2) yes
C(1) C(2) 1.534(2) yes
C(1) C(5) 1.520(2) yes
C(2) C(3) 1.534(2) yes
C(2) C(7) 1.511(2) yes
C(3) C(4) 1.557(2) yes
C(3) C(13) 1.513(2) yes
C(4) C(15) 1.525(2) yes
C(7) C(8) 1.383(2) yes
C(7) C(12) 1.391(2) yes
C(8) C(9) 1.397(2) yes
C(9) C(10) 1.382(3) yes
C(10) C(11) 1.374(3) yes
C(11) C(12) 1.390(2) yes
C(13) C(14) 1.497(3) yes
C(15) C(16) 1.390(2) yes
C(15) C(20) 1.387(3) yes
C(16) C(17) 1.393(2) yes
C(17) C(18) 1.372(3) yes
C(18) C(19) 1.379(3) yes
C(19) C(20) 1.391(2) yes
N(1) H(1) 0.913 no
C(1) H(2) 1.000 no
C(2) H(3) 1.000 no
C(3) H(4) 1.000 no
C(4) H(5) 1.000 no
C(6) H(6) 0.980 no
C(6) H(7) 0.980 no
C(6) H(8) 0.980 no
C(8) H(9) 0.950 no
C(9) H(10) 0.950 no
C(10) H(11) 0.950 no
C(11) H(12) 0.950 no
C(12) H(13) 0.950 no
C(14) H(14) 0.980 no
C(14) H(15) 0.980 no
C(14) H(16) 0.980 no
C(16) H(17) 0.950 no
C(17) H(18) 0.950 no
C(19) H(19) 0.950 no
C(20) H(20) 0.950 no
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
C(6) O(2) C(5) O(1) 5.5(2)
C(6) O(2) C(5) C(1) -173.80(16)
C(1) N(1) C(4) C(3) 1.15(19)
C(1) N(1) C(4) C(15) -121.76(16)
C(4) N(1) C(1) C(2) 23.65(19)
C(4) N(1) C(1) C(5) 142.41(15)
N(1) C(1) C(2) C(3) -38.44(17)
N(1) C(1) C(2) C(7) -164.48(15)
N(1) C(1) C(5) O(1) -60.9(2)
N(1) C(1) C(5) O(2) 118.40(17)
C(2) C(1) C(5) O(1) 53.4(2)
C(2) C(1) C(5) O(2) -127.30(16)
C(5) C(1) C(2) C(3) -155.91(14)
C(5) C(1) C(2) C(7) 78.04(19)
C(1) C(2) C(3) C(4) 39.04(16)
C(1) C(2) C(3) C(13) 164.72(14)
C(1) C(2) C(7) C(8) -106.3(2)
C(1) C(2) C(7) C(12) 71.2(2)
C(3) C(2) C(7) C(8) 136.25(19)
C(3) C(2) C(7) C(12) -46.2(2)
C(7) C(2) C(3) C(4) 163.30(15)
C(7) C(2) C(3) C(13) -71.0(2)
C(2) C(3) C(4) N(1) -25.45(18)
C(2) C(3) C(4) C(15) 95.26(18)
C(2) C(3) C(13) O(3) -14.5(2)
C(2) C(3) C(13) C(14) 162.89(15)
C(4) C(3) C(13) O(3) 105.0(2)
C(4) C(3) C(13) C(14) -77.6(2)
C(13) C(3) C(4) N(1) -150.38(16)
C(13) C(3) C(4) C(15) -29.7(2)
N(1) C(4) C(15) C(16) -147.72(19)
N(1) C(4) C(15) C(20) 33.6(2)
C(3) C(4) C(15) C(16) 95.6(2)
C(3) C(4) C(15) C(20) -83.1(2)
C(2) C(7) C(8) C(9) 178.89(18)
C(2) C(7) C(12) C(11) -178.92(19)
C(8) C(7) C(12) C(11) -1.3(3)
C(12) C(7) C(8) C(9) 1.2(3)
C(7) C(8) C(9) C(10) 0.0(2)
C(8) C(9) C(10) C(11) -1.3(3)
C(9) C(10) C(11) C(12) 1.2(3)
C(10) C(11) C(12) C(7) 0.1(2)
C(4) C(15) C(16) C(17) -176.0(2)
C(4) C(15) C(20) C(19) 176.09(19)
C(16) C(15) C(20) C(19) -2.6(3)
C(20) C(15) C(16) C(17) 2.7(3)
C(15) C(16) C(17) C(18) -0.2(3)
C(16) C(17) C(18) Cl(1) 178.31(17)
C(16) C(17) C(18) C(19) -2.5(3)
Cl(1) C(18) C(19) C(20) -178.20(16)
C(17) C(18) C(19) C(20) 2.6(3)
C(18) C(19) C(20) C(15) 0.0(2)
