#------------------------------------------------------------------------------
#$Date: 2020-04-04 07:24:41 +0300 (Sat, 04 Apr 2020) $
#$Revision: 250097 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038118.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_4038118
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         'C15 H8 O4'
_chemical_formula_sum            'C15 H8 O4'
_chemical_formula_weight         252.21
_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     dual
_audit_creation_date             2018-08-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.09(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.217(11)
_cell_length_b                   12.573(9)
_cell_length_c                   9.542(8)
_cell_measurement_reflns_used    6594
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.524
_cell_measurement_theta_min      2.704
_cell_volume                     1091.9(18)
_computing_cell_refinement       'SAINT V8.38A (Madison, 2016)'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SAINT V8.38A (Madison, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.96
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'fixed-chi two circle goniometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12122
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.701
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_type              'Incoatec Mo I\ms'
_diffrn_source_voltage           0.6
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1123 before and 0.0342 after correction. The Ratio of minimum to maximum transmission is 0.9450. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and hexane  by solvent layering'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0363
_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)+(0.0358P)²+0.6561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0901
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2215
_reflns_number_total             2497
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00567_si_002.cif
_cod_data_source_block           esser_jw255_0m_a
_cod_depositor_comments
'Adding full bibliography for 4038114--4038124.cif.'
_cod_database_code               4038118
_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_max   0.988
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 800'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.51503(10) 0.57857(8) 0.63664(9) 0.0200(2) Uani 1 1 d . . . . .
C1 C 0.36790(14) 0.59888(10) 0.57483(13) 0.0178(3) Uani 1 1 d . . . . .
O2 O 0.29941(10) 0.66106(7) 0.67327(9) 0.0197(2) Uani 1 1 d . . . . .
C2 C 0.27451(14) 0.49690(10) 0.54091(13) 0.0182(3) Uani 1 1 d . . . . .
O3 O 0.28121(11) 0.41957(8) 0.61655(10) 0.0247(2) Uani 1 1 d . . . . .
C3 C 0.17728(14) 0.51799(10) 0.40490(13) 0.0171(3) Uani 1 1 d . . . . .
C4 C 0.05907(15) 0.45780(11) 0.33918(14) 0.0201(3) Uani 1 1 d . . . . .
H4 H 0.031734 0.393426 0.380139 0.024 Uiso 1 1 calc R . . . .
O4 O 0.42710(11) 0.73115(8) 0.40366(10) 0.0232(2) Uani 1 1 d . . . . .
C5 C -0.01747(15) 0.49512(11) 0.21172(14) 0.0219(3) Uani 1 1 d . . . . .
H5 H -0.098608 0.455572 0.164571 0.026 Uiso 1 1 calc R . . . .
C6 C 0.02277(15) 0.58998(11) 0.15142(14) 0.0211(3) Uani 1 1 d . . . . .
H6 H -0.032589 0.614183 0.064817 0.025 Uiso 1 1 calc R . . . .
C7 C 0.14193(14) 0.64945(10) 0.21557(13) 0.0189(3) Uani 1 1 d . . . . .
H7 H 0.169932 0.713224 0.173602 0.023 Uiso 1 1 calc R . . . .
C8 C 0.21907(14) 0.61234(10) 0.34368(13) 0.0169(3) Uani 1 1 d . . . . .
C9 C 0.34929(14) 0.65976(10) 0.43217(13) 0.0174(3) Uani 1 1 d . . . . .
C10 C 0.39350(14) 0.65185(10) 0.80159(13) 0.0165(3) Uani 1 1 d . . . . .
C11 C 0.37012(15) 0.68732(10) 0.93225(13) 0.0193(3) Uani 1 1 d . . . . .
H11 H 0.281374 0.721447 0.945647 0.023 Uiso 1 1 calc R . . . .
C12 C 0.48533(16) 0.67007(10) 1.04468(13) 0.0211(3) Uani 1 1 d . . . . .
H12 H 0.474311 0.692368 1.137539 0.025 Uiso 1 1 calc R . . . .
C13 C 0.61478(15) 0.62129(10) 1.02352(13) 0.0205(3) Uani 1 1 d . . . . .
H13 H 0.690562 0.611078 1.102212 0.025 Uiso 1 1 calc R . . . .
C14 C 0.63685(15) 0.58651(10) 0.88858(13) 0.0188(3) Uani 1 1 d . . . . .
H14 H 0.725828 0.553726 0.873115 0.023 Uiso 1 1 calc R . . . .
C15 C 0.52196(14) 0.60282(10) 0.78053(13) 0.0167(3) 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'
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
C15 O1 C1 105.21(10) . . ?
O1 C1 O2 108.41(11) . . ?
O1 C1 C2 113.71(11) . . ?
O1 C1 C9 114.96(11) . . ?
O2 C1 C2 107.38(12) . . ?
O2 C1 C9 107.80(11) . . ?
C9 C1 C2 104.17(11) . . ?
C10 O2 C1 104.62(11) . . ?
O3 C2 C1 124.58(12) . . ?
O3 C2 C3 129.46(13) . . ?
C3 C2 C1 105.92(11) . . ?
C4 C3 C2 128.33(13) . . ?
C4 C3 C8 121.27(12) . . ?
C8 C3 C2 110.41(12) . . ?
C5 C4 C3 117.68(13) . . ?
C4 C5 C6 121.16(13) . . ?
C7 C6 C5 121.35(13) . . ?
C6 C7 C8 117.70(13) . . ?
C3 C8 C9 110.76(12) . . ?
C7 C8 C3 120.84(13) . . ?
C7 C8 C9 128.39(13) . . ?
O4 C9 C1 125.39(12) . . ?
O4 C9 C8 128.95(12) . . ?
C8 C9 C1 105.66(11) . . ?
C11 C10 O2 127.43(13) . . ?
C11 C10 C15 122.67(12) . . ?
C15 C10 O2 109.88(12) . . ?
C10 C11 C12 115.85(14) . . ?
C13 C12 C11 121.53(13) . . ?
C12 C13 C14 121.64(13) . . ?
C15 C14 C13 115.85(14) . . ?
C10 C15 O1 109.51(11) . . ?
C14 C15 O1 128.00(13) . . ?
C14 C15 C10 122.45(13) . . ?
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
O1 C1 1.414(2) . ?
O1 C15 1.3980(18) . ?
C1 O2 1.4420(17) . ?
C1 C2 1.550(2) . ?
C1 C9 1.548(2) . ?
O2 C10 1.3890(18) . ?
C2 O3 1.2066(17) . ?
C2 C3 1.480(2) . ?
C3 C4 1.392(2) . ?
C3 C8 1.4028(19) . ?
C4 C5 1.388(2) . ?
O4 C9 1.2064(18) . ?
C5 C6 1.400(2) . ?
C6 C7 1.388(2) . ?
C7 C8 1.394(2) . ?
C8 C9 1.479(2) . ?
C10 C11 1.373(2) . ?
C10 C15 1.377(2) . ?
C11 C12 1.402(2) . ?
C12 C13 1.384(2) . ?
C13 C14 1.405(2) . ?
C14 C15 1.372(2) . ?
