#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:24:41 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250097 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038116.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_4038116
loop_
_publ_author_name
'Wössner, Jan S'
'Esser, Birgit'
_publ_section_title
;
 Spiroconjugated Donor-σ-Acceptor Charge-Transfer Dyes: Effect of the
 π-Subsystems on the Optoelectronic Properties.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5048
_journal_page_last               5057
_journal_paper_doi               10.1021/acs.joc.0c00567
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C13 H8 O2'
_chemical_formula_sum            'C13 H8 O2'
_chemical_formula_weight         196.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           'FinalCif by Daniel Kratzert, Freiburg 2019'
_audit_update_record
;
2019-11-06 deposited with the CCDC.	2019-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.38(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.559(13)
_cell_length_b                   5.316(5)
_cell_length_c                   17.355(16)
_cell_measurement_reflns_used    6775
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.9515
_cell_measurement_theta_min      5.079
_cell_volume                     881.1(17)
_computing_cell_refinement       'SAINT V8.38A'
_computing_data_collection       'Bruker BIS V6.2.11/2019-03-14'
_computing_data_reduction        'SAINT V8.38A'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 HPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1011
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21945
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.734
_diffrn_reflns_theta_min         5.101
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48
(2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_recrystallization_method
'Recrystallised from ethyl acetate by slow evaporation'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.455
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.455
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0779
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1968
_refine_ls_wR_factor_ref         0.2149
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1237
_reflns_number_total             1726
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00567_si_002.cif
_cod_data_source_block           JW43_0m_a
_cod_depositor_comments
'Adding full bibliography for 4038114--4038124.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038116
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.923
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.5020(2) 0.7874(4) 0.38269(12) 0.0410(6) Uani 1 1 d . . . . .
O002 O 0.2144(2) 0.0629(4) 0.34859(12) 0.0434(6) Uani 1 1 d . . . . .
C003 C 0.2487(3) 0.3689(5) 0.45056(17) 0.0361(7) Uani 1 1 d . . . . .
C004 C 0.2377(3) 0.6653(5) 0.58202(17) 0.0359(7) Uani 1 1 d . . . . .
C005 C 0.3338(3) 0.5848(5) 0.46002(17) 0.0347(7) Uani 1 1 d . . . . .
C006 C 0.4180(3) 0.6195(5) 0.39232(17) 0.0372(7) Uani 1 1 d . . . . .
C007 C 0.3292(3) 0.7334(5) 0.52504(17) 0.0367(7) Uani 1 1 d . . . . .
H007 H 0.386798 0.878274 0.530851 0.044 Uiso 1 1 calc R U . . .
C008 C 0.1499(3) 0.4472(5) 0.57173(17) 0.0365(7) Uani 1 1 d . . . . .
C009 C 0.0555(3) 0.3889(5) 0.62967(17) 0.0386(7) Uani 1 1 d . . . . .
H009 H -0.002780 0.244603 0.624510 0.046 Uiso 1 1 calc R U . . .
C00A C 0.1585(3) 0.2987(5) 0.50543(18) 0.0378(7) Uani 1 1 d . . . . .
H00A H 0.102476 0.152014 0.498819 0.045 Uiso 1 1 calc R U . . .
C00B C 0.1360(3) 0.7515(6) 0.70368(18) 0.0404(7) Uani 1 1 d . . . . .
H00B H 0.130622 0.850560 0.749016 0.048 Uiso 1 1 calc R U . . .
C00C C 0.2725(3) 0.2507(5) 0.37516(18) 0.0383(7) Uani 1 1 d . . . . .
C00D C 0.2280(3) 0.8138(5) 0.64946(17) 0.0380(7) Uani 1 1 d . . . . .
H00D H 0.286233 0.957404 0.656670 0.046 Uiso 1 1 calc R U . . .
C00E C 0.3818(3) 0.4066(5) 0.33654(18) 0.0401(7) Uani 1 1 d . . . . .
H00C H 0.344062 0.473933 0.286716 0.048 Uiso 1 1 calc R U . . .
H00E H 0.465755 0.303998 0.326997 0.048 Uiso 1 1 calc R U . . .
C00F C 0.0481(3) 0.5393(6) 0.69292(18) 0.0423(8) Uani 1 1 d . . . . .
H00F H -0.017749 0.500785 0.730705 0.051 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C00A C003 C005 121.3(3) . . ?
C00A C003 C00C 128.9(3) . . ?
C005 C003 C00C 109.8(3) . . ?
C007 C004 C00D 120.3(3) . . ?
C007 C004 C008 120.1(3) . . ?
C00D C004 C008 119.6(3) . . ?
C007 C005 C003 121.5(3) . . ?
C007 C005 C006 128.5(3) . . ?
C003 C005 C006 110.0(3) . . ?
O001 C006 C005 126.2(3) . . ?
O001 C006 C00E 126.3(3) . . ?
C005 C006 C00E 107.4(2) . . ?
C005 C007 C004 118.3(3) . . ?
C005 C007 H007 120.9 . . ?
C004 C007 H007 120.9 . . ?
C00A C008 C009 121.4(3) . . ?
C00A C008 C004 120.2(3) . . ?
C009 C008 C004 118.4(3) . . ?
C00F C009 C008 120.0(3) . . ?
C00F C009 H009 120.0 . . ?
C008 C009 H009 120.0 . . ?
C003 C00A C008 118.7(3) . . ?
C003 C00A H00A 120.7 . . ?
C008 C00A H00A 120.7 . . ?
C00D C00B C00F 120.1(3) . . ?
C00D C00B H00B 119.9 . . ?
C00F C00B H00B 119.9 . . ?
O002 C00C C003 126.6(3) . . ?
O002 C00C C00E 126.3(3) . . ?
C003 C00C C00E 107.1(3) . . ?
C00B C00D C004 120.2(3) . . ?
C00B C00D H00D 119.9 . . ?
C004 C00D H00D 119.9 . . ?
C00C C00E C006 105.6(2) . . ?
C00C C00E H00C 110.6 . . ?
C006 C00E H00C 110.6 . . ?
C00C C00E H00E 110.6 . . ?
C006 C00E H00E 110.6 . . ?
H00C C00E H00E 108.8 . . ?
C009 C00F C00B 121.6(3) . . ?
C009 C00F H00F 119.2 . . ?
C00B C00F H00F 119.2 . . ?
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
O001 C006 1.217(3) . ?
O002 C00C 1.223(4) . ?
C003 C00A 1.363(4) . ?
C003 C005 1.412(4) . ?
C003 C00C 1.478(4) . ?
C004 C007 1.395(4) . ?
C004 C00D 1.418(4) . ?
C004 C008 1.437(4) . ?
C005 C007 1.380(4) . ?
C005 C006 1.463(4) . ?
C006 C00E 1.520(4) . ?
C007 H007 0.9500 . ?
C008 C00A 1.401(4) . ?
C008 C009 1.413(4) . ?
C009 C00F 1.362(4) . ?
C009 H009 0.9500 . ?
C00A H00A 0.9500 . ?
C00B C00D 1.355(4) . ?
C00B C00F 1.414(4) . ?
C00B H00B 0.9500 . ?
C00C C00E 1.511(4) . ?
C00D H00D 0.9500 . ?
C00E H00C 0.9900 . ?
C00E H00E 0.9900 . ?
C00F H00F 0.9500 . ?
