#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/34/7213438.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7213438
loop_
_publ_author_name
'Shi, Min'
'Jiang, Jian-Kang'
'Cui, Shi-Cong'
'Feng, Yan-Shu'
_publ_section_title
;
 Titanium(IV) chloride, zirconium(IV) chloride or boron trichloride and
 phosphine-promoted Baylis--Hillman reaction of aldehydes with
 α,β-unsaturated ketone
;
_journal_issue                   4
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              390
_journal_paper_doi               10.1039/b008105l
_journal_year                    2001
_chemical_formula_moiety         'C11 H12 Cl N O4 '
_chemical_formula_sum            'C11 H12 Cl N O4'
_chemical_formula_weight         257.67
_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
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.615(1)
_cell_length_b                   14.277(1)
_cell_length_c                   7.838(1)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    297.2
_cell_measurement_theta_max      14.7
_cell_measurement_theta_min      12.7
_cell_volume                     1187.9(2)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.10'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1601
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_standards_decay_%        1.01
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_process_details   psi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.16
_refine_ls_extinction_coef       0.003(5)
_refine_ls_extinction_method     'Zachariasen(1967) type 2 Gaussian isotropic'
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     203
_refine_ls_number_reflns         1582
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.0016
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00046|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0515
_reflns_number_gt                1108
_reflns_number_total             1582
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            b008105lsup1.cif
_cod_data_source_block           20000117b
_cod_original_cell_volume        1187.8(3)
_cod_original_sg_symbol_H-M      'P 21 21 21   '
_cod_original_formula_sum        'C11 H12 Cl N O4 '
_cod_database_code               7213438
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-x,1/2+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_calc_flag
Cl(1) Cl 0.10171(9) -0.16232(8) -0.5180(1) 0.0671(3) Uani 1.00 d
O(1) O -0.2486(4) -0.4903(2) -1.1906(4) 0.0700(8) Uani 1.00 d
O(2) O -0.0876(3) -0.4413(2) -1.3316(4) 0.0782(10) Uani 1.00 d
O(3) O -0.2829(2) -0.0779(2) -0.7318(3) 0.0580(8) Uani 1.00 d
O(4) O -0.0614(3) 0.0292(2) -0.5050(4) 0.0694(8) Uani 1.00 d
N(1) N -0.1697(3) -0.4315(2) -1.2239(4) 0.0540(9) Uani 1.00 d
C(1) C -0.1741(3) -0.3420(2) -1.1285(4) 0.0435(8) Uani 1.00 d
C(2) C -0.1017(3) -0.2679(3) -1.1840(4) 0.0489(8) Uani 1.00 d
C(3) C -0.1075(4) -0.1852(2) -1.0948(4) 0.0485(9) Uani 1.00 d
C(4) C -0.1822(3) -0.1765(2) -0.9493(4) 0.0409(7) Uani 1.00 d
C(5) C -0.2537(3) -0.2530(3) -0.8978(4) 0.0468(9) Uani 1.00 d
C(6) C -0.2509(3) -0.3360(2) -0.9873(4) 0.0478(8) Uani 1.00 d
C(7) C -0.1816(3) -0.0857(2) -0.8485(4) 0.0448(8) Uani 1.00 d
C(8) C -0.0601(3) -0.0760(2) -0.7404(4) 0.0402(8) Uani 1.00 d
C(9) C -0.0529(4) -0.1527(3) -0.6077(5) 0.0544(10) Uani 1.00 d
C(10) C -0.0564(3) 0.0207(2) -0.6586(5) 0.0489(9) Uani 1.00 d
C(11) C -0.0457(6) 0.1041(3) -0.7726(8) 0.079(2) Uani 1.00 d
H(1) H -0.047(4) -0.279(3) -1.279(5) 0.069(10) Uiso 1.00 calc
H(2) H -0.063(4) -0.139(3) -1.129(4) 0.052(9) Uiso 1.00 calc
H(3) H -0.302(3) -0.245(3) -0.798(5) 0.053(9) Uiso 1.00 calc
H(4) H -0.298(3) -0.386(2) -0.949(4) 0.050(9) Uiso 1.00 calc
H(5) H -0.182(3) -0.034(2) -0.927(4) 0.034(7) Uiso 1.00 calc
H(6) H -0.350(5) -0.072(4) -0.787(7) 0.104(9) Uiso 1.00 calc
H(7) H 0.010(4) -0.081(3) -0.816(5) 0.055(10) Uiso 1.00 calc
H(8) H -0.072(4) -0.214(3) -0.658(5) 0.055(9) Uiso 1.00 calc
H(9) H -0.108(3) -0.132(2) -0.514(5) 0.052(9) Uiso 1.00 calc
H(10) H -0.108(5) 0.101(4) -0.853(7) 0.102(9) Uiso 1.00 calc
H(11) H 0.031(8) 0.109(5) -0.826(9) 0.163(6) Uiso 1.00 calc
H(12) H -0.065(7) 0.151(5) -0.708(9) 0.161(7) Uiso 1.00 calc
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)
;
Cl Cl 0.148 0.159
;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)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(7) O(3) H(6) 108(3) 1_555 1_555 no
O(1) N(1) O(2) 124.1(3) 1_555 1_555 yes
O(1) N(1) C(1) 117.8(3) 1_555 1_555 yes
O(2) N(1) C(1) 118.1(3) 1_555 1_555 yes
N(1) C(1) C(2) 119.0(3) 1_555 1_555 yes
N(1) C(1) C(6) 118.6(3) 1_555 1_555 yes
C(2) C(1) C(6) 122.4(3) 1_555 1_555 yes
C(1) C(2) C(3) 118.3(3) 1_555 1_555 yes
C(1) C(2) H(1) 117(2) 1_555 1_555 no
C(3) C(2) H(1) 124(2) 1_555 1_555 no
C(2) C(3) C(4) 121.2(3) 1_555 1_555 yes
C(2) C(3) H(2) 118(2) 1_555 1_555 no
C(4) C(3) H(2) 120(2) 1_555 1_555 no
C(3) C(4) C(5) 118.6(3) 1_555 1_555 yes
C(3) C(4) C(7) 119.9(3) 1_555 1_555 yes
C(5) C(4) C(7) 121.5(3) 1_555 1_555 yes
C(4) C(5) C(6) 121.1(3) 1_555 1_555 yes
C(4) C(5) H(3) 116(2) 1_555 1_555 no
C(6) C(5) H(3) 122(2) 1_555 1_555 no
C(1) C(6) C(5) 118.4(3) 1_555 1_555 yes
C(1) C(6) H(4) 122(2) 1_555 1_555 no
C(5) C(6) H(4) 119(2) 1_555 1_555 no
O(3) C(7) C(4) 113.6(3) 1_555 1_555 yes
O(3) C(7) C(8) 105.8(3) 1_555 1_555 yes
O(3) C(7) H(5) 110(1) 1_555 1_555 no
C(4) C(7) C(8) 111.4(3) 1_555 1_555 yes
C(4) C(7) H(5) 109(1) 1_555 1_555 no
C(8) C(7) H(5) 106(1) 1_555 1_555 no
C(7) C(8) C(9) 110.7(3) 1_555 1_555 yes
C(7) C(8) C(10) 109.5(3) 1_555 1_555 yes
C(7) C(8) H(7) 107(2) 1_555 1_555 no
C(9) C(8) C(10) 111.5(3) 1_555 1_555 yes
C(9) C(8) H(7) 109(2) 1_555 1_555 no
C(10) C(8) H(7) 108(2) 1_555 1_555 no
Cl(1) C(9) C(8) 111.8(3) 1_555 1_555 yes
Cl(1) C(9) H(8) 106(2) 1_555 1_555 no
Cl(1) C(9) H(9) 105(1) 1_555 1_555 no
C(8) C(9) H(8) 111(2) 1_555 1_555 no
C(8) C(9) H(9) 105(2) 1_555 1_555 no
H(8) C(9) H(9) 116(2) 1_555 1_555 no
O(4) C(10) C(8) 120.5(4) 1_555 1_555 yes
O(4) C(10) C(11) 121.3(4) 1_555 1_555 yes
C(8) C(10) C(11) 118.2(3) 1_555 1_555 yes
C(10) C(11) H(10) 108(3) 1_555 1_555 no
C(10) C(11) H(11) 113(4) 1_555 1_555 no
C(10) C(11) H(12) 104(4) 1_555 1_555 no
H(10) C(11) H(11) 109(5) 1_555 1_555 no
H(10) C(11) H(12) 105(5) 1_555 1_555 no
H(11) C(11) H(12) 114(6) 1_555 1_555 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl(1) C(9) 1.791(4) yes
O(1) N(1) 1.215(4) yes
O(2) N(1) 1.221(4) yes
O(3) C(7) 1.417(4) yes
O(3) H(6) 0.84(5) no
O(4) C(10) 1.211(4) yes
N(1) C(1) 1.480(4) yes
C(1) C(2) 1.378(4) yes
C(1) C(6) 1.377(4) yes
C(2) C(3) 1.373(5) yes
C(2) H(1) 0.96(4) no
C(3) C(4) 1.395(4) yes
C(3) H(2) 0.86(4) no
C(4) C(5) 1.390(4) yes
C(4) C(7) 1.519(4) yes
C(5) C(6) 1.377(5) yes
C(5) H(3) 0.95(4) no
C(6) H(4) 0.93(3) no
C(7) C(8) 1.549(4) yes
C(7) H(5) 0.96(3) no
C(8) C(9) 1.513(5) yes
C(8) C(10) 1.522(5) yes
C(8) H(7) 0.95(4) no
C(9) H(8) 0.98(4) no
C(9) H(9) 0.98(4) no
C(10) C(11) 1.493(6) yes
C(11) H(10) 0.92(5) no
C(11) H(11) 0.92(8) no
C(11) H(12) 0.87(7) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
Cl(1) H(1) 2.96(4) 1_556
Cl(1) H(3) 2.99(4) 3_544
Cl(1) O(1) 3.337(4) 4_553
Cl(1) N(1) 3.431(3) 3_543
Cl(1) H(12) 3.45(7) 4_543
Cl(1) H(2) 3.53(4) 1_556
Cl(1) H(10) 3.53(6) 4_543
Cl(1) O(1) 3.534(3) 3_543
O(1) H(4) 2.73(3) 2_444
O(1) H(7) 2.76(4) 3_443
O(1) H(11) 2.89(8) 3_443
O(1) C(6) 3.399(4) 2_444
O(1) O(2) 3.448(5) 2_445
O(1) C(8) 3.482(5) 3_443
O(1) C(10) 3.501(5) 3_443
O(1) C(11) 3.559(7) 3_443
O(2) H(6) 2.69(5) 3_543
O(2) H(11) 2.85(8) 4_542
O(2) H(4) 2.89(3) 2_444
O(2) O(4) 3.105(4) 4_543
O(2) H(2) 3.25(4) 4_542
O(2) O(3) 3.283(4) 3_543
O(2) H(10) 3.28(6) 4_542
O(2) C(11) 3.471(7) 4_542
O(2) H(7) 3.51(4) 4_542
O(3) O(4) 2.793(4) 2_454
O(3) H(5) 2.90(3) 2_455
O(3) H(10) 3.20(6) 2_455
O(3) H(1) 3.47(4) 3_443
O(3) H(2) 3.59(4) 2_455
O(4) H(5) 2.79(3) 2_455
O(4) N(1) 3.091(4) 4_553
O(4) C(7) 3.098(4) 2_455
O(4) C(1) 3.275(4) 4_553
O(4) C(4) 3.468(4) 2_455
N(1) H(4) 3.16(3) 2_444
N(1) H(6) 3.39(5) 3_543
N(1) H(7) 3.42(4) 3_443
C(1) H(7) 3.56(4) 3_443
C(2) H(3) 3.19(4) 3_543
C(2) H(9) 3.24(4) 1_554
C(2) H(6) 3.52(5) 3_543
C(3) H(9) 3.37(4) 1_554
C(3) H(4) 3.45(3) 3_543
C(3) H(3) 3.49(4) 3_543
C(4) H(12) 3.38(8) 2_454
C(5) H(12) 3.42(8) 2_454
C(5) H(1) 3.44(4) 3_443
C(5) H(11) 3.54(8) 4_543
C(6) H(7) 3.20(4) 3_443
C(6) H(2) 3.45(4) 3_443
C(6) H(11) 3.47(8) 4_543
C(9) H(1) 3.14(4) 1_556
C(9) H(12) 3.39(7) 4_543
C(9) H(11) 3.45(8) 4_543
C(10) H(6) 3.16(5) 2_455
C(10) H(5) 3.32(3) 2_455
C(11) H(8) 2.93(4) 4_553
H(1) H(3) 2.69(5) 3_543
H(1) H(9) 2.87(6) 1_554
H(1) H(6) 3.02(7) 3_543
H(1) H(8) 3.12(6) 1_554
H(1) H(11) 3.49(9) 4_542
H(2) H(4) 2.90(5) 3_543
H(2) H(9) 3.05(5) 1_554
H(2) H(3) 3.28(5) 3_543
H(2) H(6) 3.38(6) 2_454
H(4) H(7) 2.79(5) 3_443
H(4) H(11) 3.56(8) 4_543
H(5) H(6) 3.23(6) 2_454
H(5) H(9) 3.32(5) 2_454
H(6) H(9) 3.44(6) 2_454
H(6) H(10) 3.45(8) 2_455
H(6) H(12) 3.60(9) 2_454
H(8) H(11) 2.57(8) 4_543
H(8) H(12) 2.63(8) 4_543
H(8) H(10) 3.26(7) 4_543
H(9) H(10) 3.30(7) 2_455
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
Cl(1) C(9) C(8) C(7) 165.1(2) 1_555 1_555 1_555 1_555 yes
Cl(1) C(9) C(8) C(10) -72.8(4) 1_555 1_555 1_555 1_555 yes
O(1) N(1) C(1) C(2) -168.2(3) 1_555 1_555 1_555 1_555 yes
O(1) N(1) C(1) C(6) 11.7(5) 1_555 1_555 1_555 1_555 yes
O(2) N(1) C(1) C(2) 11.4(5) 1_555 1_555 1_555 1_555 yes
O(2) N(1) C(1) C(6) -168.7(3) 1_555 1_555 1_555 1_555 yes
O(3) C(7) C(4) C(3) 165.1(3) 1_555 1_555 1_555 1_555 yes
O(3) C(7) C(4) C(5) -16.5(4) 1_555 1_555 1_555 1_555 yes
O(3) C(7) C(8) C(9) 60.4(4) 1_555 1_555 1_555 1_555 yes
O(3) C(7) C(8) C(10) -62.9(3) 1_555 1_555 1_555 1_555 yes
O(4) C(10) C(8) C(7) 115.3(4) 1_555 1_555 1_555 1_555 yes
O(4) C(10) C(8) C(9) -7.5(5) 1_555 1_555 1_555 1_555 yes
N(1) C(1) C(2) C(3) 179.6(3) 1_555 1_555 1_555 1_555 yes
N(1) C(1) C(6) C(5) 179.3(3) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(3) C(4) 1.5(5) 1_555 1_555 1_555 1_555 yes
C(1) C(6) C(5) C(4) 0.7(5) 1_555 1_555 1_555 1_555 yes
C(2) C(1) C(6) C(5) -0.8(5) 1_555 1_555 1_555 1_555 yes
C(2) C(3) C(4) C(5) -1.5(5) 1_555 1_555 1_555 1_555 yes
C(2) C(3) C(4) C(7) 177.0(3) 1_555 1_555 1_555 1_555 yes
C(3) C(2) C(1) C(6) -0.3(5) 1_555 1_555 1_555 1_555 yes
C(3) C(4) C(5) C(6) 0.4(5) 1_555 1_555 1_555 1_555 yes
C(3) C(4) C(7) C(8) -75.7(4) 1_555 1_555 1_555 1_555 yes
C(4) C(7) C(8) C(9) -63.4(4) 1_555 1_555 1_555 1_555 yes
C(4) C(7) C(8) C(10) 173.3(3) 1_555 1_555 1_555 1_555 yes
C(5) C(4) C(7) C(8) 102.8(4) 1_555 1_555 1_555 1_555 yes
C(6) C(5) C(4) C(7) -178.1(3) 1_555 1_555 1_555 1_555 yes
C(7) C(8) C(10) C(11) -65.0(5) 1_555 1_555 1_555 1_555 yes
C(9) C(8) C(10) C(11) 172.2(4) 1_555 1_555 1_555 1_555 yes
