#------------------------------------------------------------------------------
#$Date: 2016-02-27 09:48:31 +0200 (Sat, 27 Feb 2016) $
#$Revision: 177039 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/44/7224411.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_7224411
loop_
_publ_author_name
'Liu, Yongjun'
'Zhao, Hengmin'
'Tian, Guang'
'Du, Feng'
'Qi, Yan'
'Wen, Yonghong'
_publ_section_title
;
 A novel coupling reaction of α-halo ketones promoted by SmI3/CuI
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA26604A
_journal_year                    2016
_chemical_formula_iupac          'C16 H12 Cl2 O3'
_chemical_formula_moiety         'C16 H12 Cl2 O3'
_chemical_formula_sum            'C16 H12 Cl2 O3'
_chemical_formula_weight         323.16
_chemical_name_systematic
;
1,4-Bis(4-chlorophenyl)-2-hydroxybutane-1,4-dione
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2010-06-17 deposited with the CCDC.
2016-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.925(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   34.800(8)
_cell_length_b                   7.4221(14)
_cell_length_c                   5.6535(13)
_cell_measurement_reflns_used    1044
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.43
_cell_measurement_theta_min      2.35
_cell_volume                     1452.4(5)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3531
_diffrn_reflns_theta_full        24.95
_diffrn_reflns_theta_max         24.95
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.453
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.213
_refine_ls_abs_structure_details nd
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1256
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0568
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1063P)²+0.4654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1629
_reflns_number_gt                998
_reflns_number_total             1256
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            c5ra26604a2.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7224411
_audit_block_doi                 10.5517/ccv73cj
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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 1.04214(18) 0.1713(8) 0.3400(11) 0.0369(15) Uani d . 1 1
H H1 1.0356 0.1204 0.4809 0.044 Uiso calc R 1 1
C C2 1.0810(2) 0.1845(10) 0.2991(14) 0.053(2) Uani d . 1 1
H H2 1.1002 0.1385 0.4089 0.063 Uiso calc R 1 1
C C3 1.0905(2) 0.2672(9) 0.0921(14) 0.049(2) Uani d . 1 1
C C4 1.0605(2) 0.3249(10) -0.0726(13) 0.049(2) Uani d . 1 1
H H4 1.0664 0.3745 -0.2154 0.058 Uiso calc R 1 1
C C5 1.0234(2) 0.3116(8) -0.0327(12) 0.0403(16) Uani d . 1 1
H H5 1.0043 0.3556 -0.1448 0.048 Uiso calc R 1 1
C C6 1.0133(2) 0.2332(8) 0.1732(12) 0.0357(16) Uani d . 1 1
C C7 0.9724(2) 0.2035(8) 0.2253(12) 0.0374(16) Uani d . 1 1
C C8 0.9403(2) 0.2685(8) 0.0412(13) 0.0383(14) Uani d U 1 1
H H8 0.9443 0.2140 -0.1121 0.046 Uiso calc R 1 1
C C9 0.9007(2) 0.2137(9) 0.1027(12) 0.0412(15) Uani d U 1 1
H H9A 0.8999 0.0839 0.1210 0.049 Uiso calc R 1 1
H H9B 0.8961 0.2678 0.2533 0.049 Uiso calc R 1 1
C C10 0.8693(2) 0.2712(9) -0.0860(13) 0.0454(18) Uani d . 1 1
C C11 0.8287(2) 0.2621(8) -0.0279(12) 0.0362(16) Uani d . 1 1
C C12 0.8185(2) 0.1854(9) 0.1838(11) 0.0444(18) Uani d . 1 1
H H12 0.8377 0.1432 0.2964 0.053 Uiso calc R 1 1
C C13 0.7794(2) 0.1712(10) 0.2287(12) 0.0465(19) Uani d . 1 1
H H13 0.7725 0.1146 0.3649 0.056 Uiso calc R 1 1
C C14 0.7524(2) 0.2427(10) 0.0672(14) 0.053(2) Uani d . 1 1
C C15 0.7606(2) 0.3157(9) -0.1456(15) 0.0489(18) Uani d . 1 1
H H15 0.7409 0.3558 -0.2564 0.059 Uiso calc R 1 1
C C16 0.7982(2) 0.3280(9) -0.1908(12) 0.0473(18) Uani d . 1 1
H H16 0.8040 0.3809 -0.3319 0.057 Uiso calc R 1 1
Cl Cl1 1.13745(6) 0.2822(4) 0.0298(3) 0.0922(9) Uani d . 1 1
Cl Cl2 0.70386(6) 0.2245(4) 0.1208(4) 0.0948(10) Uani d . 1 1
O O1 0.96490(15) 0.1328(6) 0.4095(9) 0.0515(12) Uani d . 1 1
O O2 0.94303(14) 0.4587(5) 0.0178(8) 0.0501(10) Uani d . 1 1
H H2A 0.9434 0.5058 0.1492 0.075 Uiso calc R 1 1
O O3 0.87583(16) 0.3179(10) -0.2824(10) 0.084(2) Uani d . 1 1
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_
_citation_id
_citation_doi
_citation_year
1 10.1107/S1600536810018027 2010
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 120.7(6)
C6 C1 H1 119.7
C2 C1 H1 119.7
C3 C2 C1 119.2(7)
C3 C2 H2 120.4
C1 C2 H2 120.4
C2 C3 C4 118.1(8)
C2 C3 Cl1 121.1(6)
C4 C3 Cl1 120.6(6)
C5 C4 C3 122.3(7)
C5 C4 H4 118.8
C3 C4 H4 118.8
C4 C5 C6 120.7(7)
C4 C5 H5 119.7
C6 C5 H5 119.7
C5 C6 C1 118.9(7)
C5 C6 C7 124.0(6)
C1 C6 C7 117.1(6)
O1 C7 C6 121.4(6)
O1 C7 C8 120.9(7)
C6 C7 C8 117.6(6)
O2 C8 C9 111.2(5)
O2 C8 C7 109.0(5)
C9 C8 C7 112.3(5)
O2 C8 H8 108.1
C9 C8 H8 108.1
C7 C8 H8 108.1
C10 C9 C8 111.8(5)
C10 C9 H9A 109.3
C8 C9 H9A 109.3
C10 C9 H9B 109.3
C8 C9 H9B 109.3
H9A C9 H9B 107.9
O3 C10 C11 119.3(6)
O3 C10 C9 122.8(6)
C11 C10 C9 117.8(6)
C12 C11 C16 117.0(7)
C12 C11 C10 122.6(6)
C16 C11 C10 120.4(6)
C11 C12 C13 121.2(6)
C11 C12 H12 119.4
C13 C12 H12 119.4
C14 C13 C12 117.7(6)
C14 C13 H13 121.2
C12 C13 H13 121.2
C13 C14 C15 123.6(7)
C13 C14 Cl2 117.9(6)
C15 C14 Cl2 118.2(6)
C16 C15 C14 118.8(7)
C16 C15 H15 120.6
C14 C15 H15 120.6
C15 C16 C11 121.6(7)
C15 C16 H16 119.2
C11 C16 H16 119.2
C8 O2 H2A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.384(10)
C1 C2 1.398(10)
C1 H1 0.9300
C2 C3 1.391(12)
C2 H2 0.9300
C3 C4 1.393(11)
C3 Cl1 1.711(8)
C4 C5 1.334(9)
C4 H4 0.9300
C5 C6 1.380(9)
C5 H5 0.9300
C6 C7 1.499(10)
C7 O1 1.218(8)
C7 C8 1.525(10)
C8 O2 1.422(7)
C8 C9 1.509(7)
C8 H8 0.9800
C9 C10 1.507(11)
C9 H9A 0.9700
C9 H9B 0.9700
C10 O3 1.206(9)
C10 C11 1.485(10)
C11 C12 1.404(9)
C11 C16 1.419(10)
C12 C13 1.413(9)
C12 H12 0.9300
C13 C14 1.349(11)
C13 H13 0.9300
C14 C15 1.376(12)
C14 Cl2 1.753(8)
C15 C16 1.361(10)
C15 H15 0.9300
C16 H16 0.9300
O2 H2A 0.8200
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H2A O2 2_565 0.82 2.10 2.894(6) 163
C1 H1 Cg1 2_555 0.93 2.89 3.507(6) 125
C4 H4 Cg1 2_564 0.93 2.97 3.600(6) 126
C13 H13 Cg2 2_555 0.93 2.88 3.517(6) 127
C16 H16 Cg2 2_564 0.93 2.90 3.544(6) 128
