#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:53:44 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180321 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/35/7153589.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_7153589
loop_
_publ_author_name
'Bai, Guifeng'
'Yu, Changjiang'
'Cheng, Chi'
'Hao, Erhong'
'Wei, Yun'
'Mu, Xiaolong'
'Jiao, Lijuan'
_publ_section_title
;
 Syntheses and photophysical properties of BF2 complexes of curcumin
 analogues.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1618
_journal_page_last               1626
_journal_paper_doi               10.1039/c3ob42201a
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C23 H19 B F2 O2'
_chemical_formula_sum            'C23 H19 B F2 O2'
_chemical_formula_weight         376.19
_chemical_melting_point          ?
_chemical_name_common            1j
_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                 95.180(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.957(2)
_cell_length_b                   11.8082(16)
_cell_length_c                   9.9913(14)
_cell_measurement_reflns_used    1892
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      2.41
_cell_volume                     1992.4(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  '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  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8451
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9786
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Semi-empirical from equivalents'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0577
_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)+(0.1205P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1736
_refine_ls_wR_factor_ref         0.2196
_reflns_number_gt                1119
_reflns_number_total             2306
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob42201a.txt
_cod_data_source_block           110610a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_symmetry_cell_setting' value
'Monoclinic' changed to 'monoclinic' according to
/usr/data/users/saulius/automatic-downloads/current/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 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               7153589
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C6 C 0.31136(12) 0.9417(2) 0.77497(19) 0.0687(6) Uani 1 1 d .
C2 C 0.41567(16) 0.9727(3) 0.6313(2) 0.0961(9) Uani 1 1 d .
H2 H 0.4519 1.0213 0.5967 0.115 Uiso 1 1 calc R
C1 C 0.36586(14) 1.0126(2) 0.7217(2) 0.0818(7) Uani 1 1 d .
H1 H 0.3687 1.0883 0.7476 0.098 Uiso 1 1 calc R
C5 C 0.30882(16) 0.8312(2) 0.7338(3) 0.0937(8) Uani 1 1 d .
H5 H 0.2726 0.7819 0.7673 0.112 Uiso 1 1 calc R
C3 C 0.41225(16) 0.8631(3) 0.5923(3) 0.0992(9) Uani 1 1 d .
H3 H 0.4459 0.8362 0.5310 0.119 Uiso 1 1 calc R
C4 C 0.3589(2) 0.7921(3) 0.6438(3) 0.1108(10) Uani 1 1 d .
H4 H 0.3565 0.7165 0.6175 0.133 Uiso 1 1 calc R
C8 C 0.20570(12) 0.9335(2) 0.9341(2) 0.0716(6) Uani 1 1 d .
H8 H 0.1996 0.8559 0.9205 0.086 Uiso 1 1 calc R
C10 C 0.10130(12) 0.9380(2) 1.08917(17) 0.0686(6) Uani 1 1 d .
H10 H 0.0957 0.8599 1.0805 0.082 Uiso 1 1 calc R
C9 C 0.15636(12) 0.9894(2) 1.02318(18) 0.0680(6) Uani 1 1 d .
H9 H 0.1632 1.0669 1.0359 0.082 Uiso 1 1 calc R
C7 C 0.25988(13) 0.9880(2) 0.8702(2) 0.0734(7) Uani 1 1 d .
H7 H 0.2655 1.0650 0.8886 0.088 Uiso 1 1 calc R
C12 C 0.0000 0.9394(3) 1.2500 0.0692(8) Uani 1 2 d S
H12 H 0.0000 0.8606 1.2500 0.083 Uiso 1 2 calc SR
O1 O 0.05256(8) 1.10657(14) 1.17352(14) 0.0778(5) Uani 1 1 d .
C11 C 0.05021(11) 0.99731(19) 1.17300(18) 0.0621(6) Uani 1 1 d .
B1 B 0.0000 1.1763(3) 1.2500 0.0737(10) Uani 1 2 d S
F1 F -0.04585(9) 1.24176(12) 1.16120(14) 0.0988(6) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C6 0.0628(13) 0.0823(15) 0.0631(12) -0.0008(11) 0.0166(10) 0.0026(11)
C2 0.0781(17) 0.128(3) 0.0870(17) -0.0064(16) 0.0349(14) -0.0094(16)
C1 0.0756(15) 0.0900(16) 0.0834(14) -0.0076(13) 0.0265(12) -0.0107(12)
C5 0.0993(18) 0.0834(18) 0.1048(18) -0.0043(15) 0.0438(15) -0.0032(15)
C3 0.0892(18) 0.129(3) 0.0850(16) -0.0069(17) 0.0358(14) 0.0177(18)
C4 0.128(2) 0.096(2) 0.116(2) -0.0194(16) 0.0486(19) 0.0100(18)
C8 0.0678(13) 0.0847(15) 0.0648(12) 0.0018(11) 0.0194(11) 0.0044(11)
C10 0.0742(14) 0.0715(14) 0.0637(12) 0.0004(10) 0.0255(11) 0.0012(11)
C9 0.0669(14) 0.0758(14) 0.0629(12) 0.0014(10) 0.0156(11) 0.0050(10)
C7 0.0657(13) 0.0811(15) 0.0759(13) -0.0043(11) 0.0208(11) -0.0006(11)
C12 0.079(2) 0.0603(17) 0.0726(17) 0.000 0.0299(16) 0.000
O1 0.0789(11) 0.0642(10) 0.0956(11) 0.0047(7) 0.0375(9) 0.0008(7)
C11 0.0627(13) 0.0652(13) 0.0600(11) 0.0003(10) 0.0135(10) 0.0027(10)
B1 0.080(2) 0.058(2) 0.087(2) 0.000 0.028(2) 0.000
F1 0.1078(11) 0.0878(10) 0.1045(10) 0.0174(8) 0.0293(9) 0.0246(8)
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'
B B 0.0013 0.0007 '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
C5 C6 C1 117.6(2) . .
C5 C6 C7 123.5(2) . .
C1 C6 C7 118.9(2) . .
C3 C2 C1 120.3(3) . .
C2 C1 C6 121.0(2) . .
C6 C5 C4 121.0(3) . .
C2 C3 C4 119.4(2) . .
C3 C4 C5 120.6(3) . .
C7 C8 C9 122.7(2) . .
C9 C10 C11 123.3(2) . .
C10 C9 C8 124.7(2) . .
C8 C7 C6 127.7(2) . .
C11 C12 C11 120.5(3) . 2_557
C11 O1 B1 122.67(17) . .
O1 C11 C12 120.9(2) . .
O1 C11 C10 117.95(18) . .
C12 C11 C10 121.1(2) . .
F1 B1 F1 111.1(3) 2_557 .
F1 B1 O1 108.32(8) 2_557 2_557
F1 B1 O1 108.49(8) . 2_557
F1 B1 O1 108.49(8) 2_557 .
F1 B1 O1 108.32(8) . .
O1 B1 O1 112.2(3) 2_557 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C6 C5 1.367(3) .
C6 C1 1.388(3) .
C6 C7 1.455(3) .
C2 C3 1.351(4) .
C2 C1 1.375(3) .
C5 C4 1.372(4) .
C3 C4 1.368(4) .
C8 C7 1.331(3) .
C8 C9 1.437(3) .
C10 C9 1.337(3) .
C10 C11 1.440(3) .
C12 C11 1.380(3) .
C12 C11 1.380(3) 2_557
O1 C11 1.291(3) .
O1 B1 1.476(2) .
B1 F1 1.365(2) 2_557
B1 F1 1.365(2) .
B1 O1 1.476(2) 2_557
