#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:37:28 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180148 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/45/7104502.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_7104502
loop_
_publ_author_name
'Li, Haijun'
'Li, Wenjuan'
'Li, Zhiping'
_publ_section_title
;
 Iron-catalyzed cross-aldol reactions of ortho-diketones and methyl
 ketones.
;
_journal_issue                   22
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3264
_journal_page_last               3266
_journal_paper_doi               10.1039/b903515j
_journal_volume                  34
_journal_year                    2009
_chemical_formula_sum            'C14 H7 Cl3 O3'
_chemical_formula_weight         329.55
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                62.21(3)
_cell_angle_beta                 89.89(3)
_cell_angle_gamma                89.83(3)
_cell_formula_units_Z            4
_cell_length_a                   4.1248(8)
_cell_length_b                   18.813(4)
_cell_length_c                   19.845(4)
_cell_measurement_reflns_used    12452
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.16
_cell_volume                     1362.3(5)
_computing_cell_refinement       Rapid-AUTO
_computing_data_collection       'Rapid-AUTO (Rigaku,2000)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC,2000)'
_computing_molecular_graphics    'Siemens SHELXTL V4.2,(Sheldrick,1990)'
_computing_publication_material  SHELXL-97,(Sheldrick,1997)
_computing_structure_refinement  SHELXL-97,(Sheldrick,1997)
_computing_structure_solution    SHELXS-97,(Sheldrick,1997)
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       Ω
_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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0835
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12452
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.16
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  0.8769
_exptl_absorpt_correction_T_min  0.7291
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
HIGASHI, T. (1995). Abscor-Empirical
Absorption Correction based on Fourier
Series Approximation.
Rigaku Corporation,Tokyo,Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         6165
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0780
_reflns_number_gt                2803
_reflns_number_total             6165
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b903515j.txt
_cod_data_source_block           lzpa
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Empirical' changed to 'empirical'
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 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7104502
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3334(6) 0.06744(15) 0.05700(15) 0.0415(7) Uani 1 1 d . . .
C2 C 0.2784(6) -0.01752(15) 0.09548(16) 0.0489(7) Uani 1 1 d . . .
H2 H 0.2256 -0.0396 0.0637 0.059 Uiso 1 1 calc R . .
C3 C 0.2903(6) -0.07006(14) 0.16929(17) 0.0442(7) Uani 1 1 d . . .
C4 C 0.3688(6) -0.05638(14) 0.23285(14) 0.0412(7) Uani 1 1 d . . .
C5 C 0.5182(6) 0.01015(15) 0.22783(14) 0.0375(6) Uani 1 1 d . . .
C6 C 0.6445(6) 0.08155(14) 0.15852(14) 0.0344(6) Uani 1 1 d . . .
C7 C 0.4801(6) 0.11430(13) 0.08512(14) 0.0345(6) Uani 1 1 d . . .
C8 C 0.4949(6) 0.20259(15) 0.03488(16) 0.0454(7) Uani 1 1 d . . .
C9 C 0.5512(6) 0.26234(14) 0.06211(15) 0.0375(6) Uani 1 1 d . . .
C10 C 0.4384(6) 0.25239(15) 0.13149(16) 0.0442(7) Uani 1 1 d . . .
H10 H 0.3406 0.2045 0.1657 0.053 Uiso 1 1 calc R . .
C11 C 0.4736(6) 0.31541(18) 0.14937(18) 0.0562(8) Uani 1 1 d . . .
H11 H 0.3977 0.3096 0.1958 0.067 Uiso 1 1 calc R . .
C12 C 0.6202(7) 0.38632(19) 0.0987(2) 0.0668(9) Uani 1 1 d . . .
H12 H 0.6423 0.4280 0.1112 0.080 Uiso 1 1 calc R . .
C13 C 0.7324(7) 0.39538(17) 0.0307(2) 0.0648(9) Uani 1 1 d . . .
H13 H 0.8333 0.4430 -0.0030 0.078 Uiso 1 1 calc R . .
C14 C 0.6967(6) 0.33380(15) 0.01148(16) 0.0519(8) Uani 1 1 d . . .
H14 H 0.7704 0.3405 -0.0354 0.062 Uiso 1 1 calc R . .
C15 C 0.1652(6) 0.56750(15) 0.55700(15) 0.0433(7) Uani 1 1 d . . .
C16 C 0.2238(6) 0.48232(15) 0.59562(16) 0.0494(7) Uani 1 1 d . . .
H16 H 0.2803 0.4601 0.5641 0.059 Uiso 1 1 calc R . .
C17 C 0.2097(6) 0.43016(14) 0.66970(16) 0.0443(7) Uani 1 1 d . . .
C18 C 0.1306(6) 0.44408(14) 0.73301(14) 0.0394(6) Uani 1 1 d . . .
C19 C -0.0165(6) 0.51048(15) 0.72724(14) 0.0366(6) Uani 1 1 d . . .
C20 C -0.1454(6) 0.58167(14) 0.65827(14) 0.0348(6) Uani 1 1 d . . .
C21 C 0.0217(6) 0.61433(13) 0.58482(14) 0.0345(6) Uani 1 1 d . . .
C22 C 0.0043(6) 0.70230(15) 0.53498(16) 0.0453(7) Uani 1 1 d . . .
C23 C -0.0502(6) 0.76194(13) 0.56226(15) 0.0390(6) Uani 1 1 d . . .
C24 C 0.0618(6) 0.75290(15) 0.63144(16) 0.0423(7) Uani 1 1 d . . .
H24 H 0.1600 0.7050 0.6656 0.051 Uiso 1 1 calc R . .
C25 C 0.0282(7) 0.81453(18) 0.64988(18) 0.0553(8) Uani 1 1 d . . .
H25 H 0.1046 0.8084 0.6963 0.066 Uiso 1 1 calc R . .
C26 C -0.1203(7) 0.88601(18) 0.5989(2) 0.0642(9) Uani 1 1 d . . .
H26 H -0.1439 0.9276 0.6115 0.077 Uiso 1 1 calc R . .
C27 C -0.2309(7) 0.89537(17) 0.5307(2) 0.0665(9) Uani 1 1 d . . .
H27 H -0.3296 0.9434 0.4970 0.080 Uiso 1 1 calc R . .
C28 C -0.1977(6) 0.83419(15) 0.51129(16) 0.0515(8) Uani 1 1 d . . .
H28 H -0.2731 0.8410 0.4645 0.062 Uiso 1 1 calc R . .
Cl1 Cl 0.1931(2) -0.16810(4) 0.19076(5) 0.0909(3) Uani 1 1 d . . .
Cl2 Cl 0.26432(19) -0.13142(5) 0.32199(4) 0.0701(2) Uani 1 1 d . . .
Cl3 Cl 0.60071(19) 0.01778(5) 0.30876(4) 0.0671(2) Uani 1 1 d . . .
Cl4 Cl 0.3074(2) 0.33208(4) 0.69070(5) 0.0910(3) Uani 1 1 d . . .
Cl5 Cl 0.2355(2) 0.36858(5) 0.82204(4) 0.0704(2) Uani 1 1 d . . .
Cl6 Cl -0.1009(2) 0.51776(5) 0.80869(4) 0.0677(2) Uani 1 1 d . . .
H1 H 0.302(9) 0.158(3) -0.034(2) 0.138(15) Uiso 1 1 d . . .
H4 H 0.194(8) 0.6539(13) 0.464(2) 0.129(14) Uiso 1 1 d D . .
O1 O 0.2309(5) 0.09896(13) -0.01478(12) 0.0687(6) Uani 1 1 d . . .
O2 O 0.4390(6) 0.22841(12) -0.03421(11) 0.0815(7) Uani 1 1 d . . .
O3 O 0.8827(4) 0.11577(10) 0.16616(11) 0.0493(5) Uani 1 1 d . . .
O4 O 0.2701(5) 0.59898(12) 0.48512(11) 0.0680(6) Uani 1 1 d D . .
O5 O 0.0622(6) 0.72845(11) 0.46593(11) 0.0819(7) Uani 1 1 d . . .
O6 O -0.3831(4) 0.61581(10) 0.66639(11) 0.0493(5) Uani 1 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O1 C1 C7 121.4(2) . . ?
O1 C1 C2 110.4(2) . . ?
C7 C1 C2 128.1(2) . . ?
C3 C2 C1 130.7(3) . . ?
C3 C2 H2 114.7 . . ?
C1 C2 H2 114.7 . . ?
C2 C3 C4 128.9(2) . . ?
C2 C3 Cl1 114.8(2) . . ?
C4 C3 Cl1 116.2(2) . . ?
C5 C4 C3 125.1(2) . . ?
C5 C4 Cl2 118.3(2) . . ?
C3 C4 Cl2 116.54(19) . . ?
C4 C5 C6 128.9(2) . . ?
C4 C5 Cl3 120.0(2) . . ?
C6 C5 Cl3 111.07(19) . . ?
O3 C6 C7 119.8(2) . . ?
O3 C6 C5 117.7(2) . . ?
C7 C6 C5 122.3(2) . . ?
C1 C7 C6 123.7(2) . . ?
C1 C7 C8 118.1(2) . . ?
C6 C7 C8 118.0(2) . . ?
O2 C8 C9 117.4(2) . . ?
O2 C8 C7 118.1(2) . . ?
C9 C8 C7 124.4(2) . . ?
C10 C9 C14 120.3(2) . . ?
C10 C9 C8 122.6(2) . . ?
C14 C9 C8 116.8(2) . . ?
C9 C10 C11 118.8(3) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 120.0(3) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
O4 C15 C21 121.4(2) . . ?
O4 C15 C16 110.2(2) . . ?
C21 C15 C16 128.5(2) . . ?
C17 C16 C15 130.1(3) . . ?
C17 C16 H16 114.9 . . ?
C15 C16 H16 114.9 . . ?
C16 C17 C18 129.3(2) . . ?
C16 C17 Cl4 114.0(2) . . ?
C18 C17 Cl4 116.6(2) . . ?
C19 C18 C17 124.7(2) . . ?
C19 C18 Cl5 119.2(2) . . ?
C17 C18 Cl5 116.14(19) . . ?
C18 C19 C20 129.6(2) . . ?
C18 C19 Cl6 119.2(2) . . ?
C20 C19 Cl6 111.05(19) . . ?
O6 C20 C21 120.4(2) . . ?
O6 C20 C19 117.7(2) . . ?
C21 C20 C19 121.7(2) . . ?
C15 C21 C20 123.6(2) . . ?
C15 C21 C22 118.6(2) . . ?
C20 C21 C22 117.6(2) . . ?
O5 C22 C23 117.1(2) . . ?
O5 C22 C21 118.1(2) . . ?
C23 C22 C21 124.5(2) . . ?
C24 C23 C28 119.5(2) . . ?
C24 C23 C22 123.6(2) . . ?
C28 C23 C22 116.7(2) . . ?
C25 C24 C23 120.2(3) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 119.9(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C27 C26 C25 120.3(3) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 120.5(3) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C27 C28 C23 119.7(3) . . ?
C27 C28 H28 120.2 . . ?
C23 C28 H28 120.2 . . ?
C1 O1 H1 100(2) . . ?
C8 O2 H1 100.4(16) . . ?
C15 O4 H4 102(2) . . ?
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 O1 1.331(3) . ?
C1 C7 1.385(3) . ?
C1 C2 1.433(3) . ?
C2 C3 1.332(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.438(4) . ?
C3 Cl1 1.736(3) . ?
C4 C5 1.358(3) . ?
C4 Cl2 1.726(3) . ?
C5 C6 1.499(3) . ?
C5 Cl3 1.713(3) . ?
C6 O3 1.224(3) . ?
C6 C7 1.458(3) . ?
C7 C8 1.488(3) . ?
C8 O2 1.244(3) . ?
C8 C9 1.476(3) . ?
C9 C10 1.380(3) . ?
C9 C14 1.385(3) . ?
C10 C11 1.395(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.360(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O4 1.336(3) . ?
C15 C21 1.372(3) . ?
C15 C16 1.438(3) . ?
C16 C17 1.335(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.435(4) . ?
C17 Cl4 1.738(2) . ?
C18 C19 1.343(3) . ?
C18 Cl5 1.728(2) . ?
C19 C20 1.496(3) . ?
C19 Cl6 1.720(3) . ?
C20 O6 1.222(3) . ?
C20 C21 1.463(3) . ?
C21 C22 1.482(3) . ?
C22 O5 1.244(3) . ?
C22 C23 1.472(3) . ?
C23 C24 1.382(3) . ?
C23 C28 1.399(3) . ?
C24 C25 1.375(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.392(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.359(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.381(4) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
O1 H1 1.03(5) . ?
O2 H1 1.44(5) . ?
O4 H4 0.968(19) . ?
