#------------------------------------------------------------------------------
#$Date: 2019-11-24 02:31:32 +0100 (dom 24 de nov de 2019) $
#$Revision: 236507 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/67/7236775.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_7236775
loop_
_publ_author_name
'Chen, Ya-Wen'
'Lin, Yen-Chun'
'Kuo, Hsiu-Ming'
'Lai, Chung K.'
_publ_section_title
;
 Fluorescent columnar bis(boron difluoride) complexes derived from
 tetraketonates
;
_journal_issue                   22
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              5465
_journal_paper_doi               10.1039/C7TC01425B
_journal_volume                  5
_journal_year                    2017
_chemical_formula_sum            'C30 H38 O6'
_chemical_formula_weight         494.60
_chemical_melting_point          400
_chemical_name_systematic
' (2Z,4Z)-3,4-dihydroxy-1,6-bis(4-(hexyloxy) phenyl)hexa-2,4-diene-1,6-dione'
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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
_audit_update_record
;
2017-03-31 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                94.865(2)
_cell_angle_beta                 111.294(2)
_cell_angle_gamma                96.125(2)
_cell_formula_units_Z            1
_cell_length_a                   8.0849(8)
_cell_length_b                   8.3286(9)
_cell_length_c                   10.9474(11)
_cell_measurement_reflns_used    2017
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.48
_cell_volume                     676.81(12)
_computing_cell_refinement       'Bruker SAINT'
_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      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'BRUKER SMART APEXCCD area detector'
_diffrn_measurement_method       '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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8777
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9795
_exptl_absorpt_correction_T_min  0.9595
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             266
_exptl_crystal_preparation       ', Luminescent'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0447
_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)+(0.0598P)²+0.0764P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1256
_reflns_number_gt                2294
_reflns_number_total             3108
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7tc01425b2.cif
_cod_data_source_block           ic15572
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

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

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        676.80(12)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7236775
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
O1 O 0.14084(14) -0.46523(11) -0.08901(10) 0.0452(3) Uani 1 1 d .
H1 H 0.2072 -0.3815 -0.0909 0.068 Uiso 1 1 calc R
O2 O 0.28521(12) -0.17558(11) -0.03050(10) 0.0429(3) Uani 1 1 d .
O3 O 0.34053(13) 0.48751(11) 0.31221(10) 0.0431(3) Uani 1 1 d .
C1 C 0.06080(16) -0.43083(15) -0.00596(12) 0.0324(3) Uani 1 1 d .
C2 C 0.08582(16) -0.28062(15) 0.06251(12) 0.0328(3) Uani 1 1 d .
H2 H 0.0252 -0.2622 0.1211 0.039 Uiso 1 1 calc R
C3 C 0.20380(16) -0.14960(16) 0.04657(12) 0.0324(3) Uani 1 1 d .
C4 C 0.23278(16) 0.01626(15) 0.11780(12) 0.0315(3) Uani 1 1 d .
C5 C 0.35313(16) 0.13787(16) 0.10046(13) 0.0355(3) Uani 1 1 d .
H5 H 0.4133 0.1128 0.0427 0.043 Uiso 1 1 calc R
C6 C 0.38505(17) 0.29285(17) 0.16599(13) 0.0379(3) Uani 1 1 d .
H6 H 0.4667 0.3742 0.1531 0.045 Uiso 1 1 calc R
C7 C 0.29819(17) 0.33142(16) 0.25139(13) 0.0348(3) Uani 1 1 d .
C8 C 0.17702(17) 0.21254(16) 0.26901(13) 0.0355(3) Uani 1 1 d .
H8 H 0.1164 0.2380 0.3264 0.043 Uiso 1 1 calc R
C9 C 0.14598(17) 0.05726(16) 0.20218(12) 0.0339(3) Uani 1 1 d .
H9 H 0.0631 -0.0236 0.2142 0.041 Uiso 1 1 calc R
C10 C 0.25088(19) 0.53798(17) 0.39745(14) 0.0412(3) Uani 1 1 d .
H10A H 0.2773 0.4737 0.4726 0.049 Uiso 1 1 calc R
H10B H 0.1194 0.5217 0.3481 0.049 Uiso 1 1 calc R
C11 C 0.31986(18) 0.71591(16) 0.44699(13) 0.0391(3) Uani 1 1 d .
H11A H 0.2947 0.7775 0.3703 0.047 Uiso 1 1 calc R
H11B H 0.4517 0.7297 0.4943 0.047 Uiso 1 1 calc R
C12 C 0.23599(18) 0.78709(17) 0.53930(14) 0.0396(3) Uani 1 1 d .
H12A H 0.1043 0.7746 0.4919 0.048 Uiso 1 1 calc R
H12B H 0.2602 0.7251 0.6157 0.048 Uiso 1 1 calc R
C13 C 0.30804(18) 0.96613(16) 0.58949(13) 0.0379(3) Uani 1 1 d .
H13A H 0.4398 0.9777 0.6365 0.046 Uiso 1 1 calc R
H13B H 0.2846 1.0270 0.5125 0.046 Uiso 1 1 calc R
C14 C 0.2281(2) 1.04297(18) 0.68142(14) 0.0440(3) Uani 1 1 d .
H14A H 0.2536 0.9839 0.7595 0.053 Uiso 1 1 calc R
H14B H 0.0962 1.0303 0.6352 0.053 Uiso 1 1 calc R
C15 C 0.3001(2) 1.2225(2) 0.72824(17) 0.0578(4) Uani 1 1 d .
H15A H 0.4304 1.2360 0.7755 0.087 Uiso 1 1 calc R
H15B H 0.2441 1.2647 0.7877 0.087 Uiso 1 1 calc R
H15C H 0.2720 1.2826 0.6518 0.087 Uiso 1 1 calc R
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
O1 0.0536(6) 0.0382(6) 0.0568(6) 0.0004(5) 0.0391(5) -0.0003(5)
O2 0.0442(5) 0.0416(6) 0.0529(6) 0.0018(4) 0.0324(5) 0.0008(4)
O3 0.0491(6) 0.0326(5) 0.0498(6) 0.0007(4) 0.0241(5) -0.0013(4)
C1 0.0314(6) 0.0365(7) 0.0321(6) 0.0058(5) 0.0148(5) 0.0060(5)
C2 0.0314(7) 0.0360(7) 0.0344(7) 0.0052(6) 0.0165(6) 0.0040(5)
C3 0.0276(6) 0.0385(7) 0.0325(7) 0.0067(5) 0.0122(5) 0.0060(5)
C4 0.0271(6) 0.0347(7) 0.0325(6) 0.0067(5) 0.0110(5) 0.0028(5)
C5 0.0312(7) 0.0393(7) 0.0396(7) 0.0065(6) 0.0181(6) 0.0027(5)
C6 0.0333(7) 0.0382(8) 0.0443(8) 0.0089(6) 0.0181(6) -0.0015(5)
C7 0.0340(7) 0.0324(7) 0.0344(7) 0.0056(5) 0.0089(5) 0.0027(5)
C8 0.0371(7) 0.0371(7) 0.0361(7) 0.0055(6) 0.0185(6) 0.0039(5)
C9 0.0326(7) 0.0340(7) 0.0365(7) 0.0067(5) 0.0155(6) 0.0003(5)
C10 0.0444(8) 0.0376(8) 0.0420(8) 0.0035(6) 0.0181(6) 0.0019(6)
C11 0.0407(7) 0.0348(7) 0.0396(8) 0.0048(6) 0.0134(6) 0.0020(6)
C12 0.0382(7) 0.0380(7) 0.0412(7) 0.0061(6) 0.0137(6) 0.0022(6)
C13 0.0385(7) 0.0389(8) 0.0367(7) 0.0055(6) 0.0152(6) 0.0031(6)
C14 0.0497(8) 0.0457(8) 0.0427(8) 0.0090(6) 0.0236(7) 0.0082(7)
C15 0.0688(11) 0.0515(10) 0.0588(10) -0.0021(8) 0.0325(9) 0.0098(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'
O O 0.0106 0.0060 '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_3
C7 O3 C10 118.74(10) .
O1 C1 C2 123.20(12) .
O1 C1 C1 114.65(14) 2_545
C2 C1 C1 122.15(14) 2_545
C1 C2 C3 120.12(11) .
O2 C3 C2 119.51(12) .
O2 C3 C4 118.66(11) .
C2 C3 C4 121.83(11) .
C9 C4 C5 118.21(12) .
C9 C4 C3 122.75(11) .
C5 C4 C3 119.04(11) .
C6 C5 C4 120.74(12) .
C5 C6 C7 120.29(12) .
O3 C7 C8 124.63(12) .
O3 C7 C6 115.59(11) .
C8 C7 C6 119.78(12) .
C9 C8 C7 119.27(12) .
C8 C9 C4 121.71(12) .
O3 C10 C11 106.97(11) .
C10 C11 C12 112.99(11) .
C13 C12 C11 112.41(11) .
C14 C13 C12 114.48(11) .
C13 C14 C15 113.41(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.3230(15) .
O2 C3 1.2628(14) .
O3 C7 1.3576(16) .
O3 C10 1.4362(16) .
C1 C2 1.3582(18) .
C1 C1 1.479(2) 2_545
C2 C3 1.4360(18) .
C3 C4 1.4788(18) .
C4 C9 1.3895(17) .
C4 C5 1.4018(17) .
C5 C6 1.3728(19) .
C6 C7 1.3945(18) .
C7 C8 1.3927(18) .
C8 C9 1.3812(18) .
C10 C11 1.5063(18) .
C11 C12 1.5214(19) .
C12 C13 1.5192(18) .
C13 C14 1.5136(18) .
C14 C15 1.518(2) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O2 0.84 1.75 2.4872(13) 145.9
