#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:44:41 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223595 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/20/7232086.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_7232086
loop_
_publ_author_name
'Bristow, Jonathan C.'
'Addicoat, Matthew A.'
'Wallis, John D.'
_publ_section_title
;
 O(−)⋯C interactions and bond formation in 1-naphtholate
 anions with peri-located electrophilic carbon centres
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              1009
_journal_paper_doi               10.1039/C8CE01872C
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C15 H14 O2'
_chemical_formula_sum            'C15 H14 O2'
_chemical_formula_weight         226.26
_chemical_melting_point          380.5(15)
_chemical_name_systematic
;
 3-(tert-butyl)-2H-naphtho[1,8-bc]furan-2-one
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-06-14 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0730(6)
_cell_length_b                   6.8273(4)
_cell_length_c                   12.0491(7)
_cell_measurement_reflns_used    1254
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.5760
_cell_measurement_theta_min      3.6710
_cell_volume                     1157.68(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-2014
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4309
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        27.000
_diffrn_reflns_theta_max         29.090
_diffrn_reflns_theta_min         2.895
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       Block
_exptl_crystal_F_000             480
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.568
_exptl_crystal_size_mid          0.495
_exptl_crystal_size_min          0.137
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0682P)²+0.3937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1437
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1268
_reflns_number_total             1484
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01872c2.cif
_cod_data_source_block           new555
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '379-382' was changed to '380.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7232086--7232099.cif.
;
_cod_database_code               7232086
_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.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O2 O 0.04084(11) 0.7500 0.70880(13) 0.0323(4) Uani 1 2 d S T P
O5 O 0.19283(12) 0.7500 0.76373(14) 0.0452(5) Uani 1 2 d S T P
C1 C -0.00638(15) 0.7500 0.60765(18) 0.0248(5) Uani 1 2 d S T P
C2 C -0.10177(16) 0.7500 0.5882(2) 0.0311(5) Uani 1 2 d S T P
H2 H -0.1471 0.7500 0.6466 0.037 Uiso 1 2 calc R U P
C3 C -0.12877(15) 0.7500 0.4743(2) 0.0339(6) Uani 1 2 d S T P
H3 H -0.1947 0.7500 0.4572 0.041 Uiso 1 2 calc R U P
C4 C -0.06603(16) 0.7500 0.3886(2) 0.0318(6) Uani 1 2 d S T P
H4 H -0.0885 0.7500 0.3142 0.038 Uiso 1 2 calc R U P
C5 C 0.03354(15) 0.7500 0.41022(19) 0.0244(5) Uani 1 2 d S T P
C6 C 0.11204(17) 0.7500 0.33688(18) 0.0284(5) Uani 1 2 d S T P
H6 H 0.1014 0.7500 0.2590 0.034 Uiso 1 2 calc R U P
C7 C 0.20356(16) 0.7500 0.37679(18) 0.0273(5) Uani 1 2 d S T P
H7 H 0.2538 0.7500 0.3241 0.033 Uiso 1 2 calc R U P
C8 C 0.22871(14) 0.7500 0.49133(18) 0.0209(4) Uani 1 2 d S T P
C9 C 0.15194(14) 0.7500 0.56411(17) 0.0213(4) Uani 1 2 d S T P
C10 C 0.05919(13) 0.7500 0.52153(18) 0.0209(4) Uani 1 2 d S T P
C11 C 0.13877(15) 0.7500 0.68685(18) 0.0277(5) Uani 1 2 d S T P
C12 C 0.33347(14) 0.7500 0.52825(19) 0.0257(5) Uani 1 2 d S T P
C13 C 0.40240(17) 0.7500 0.4308(2) 0.0407(6) Uani 1 2 d S T P
H13A H 0.3920 0.8677 0.3856 0.061 Uiso 1 1 d . U .
H13B H 0.4677 0.7500 0.4584 0.061 Uiso 1 2 d S U P
C14 C 0.35274(11) 0.9345(2) 0.59757(16) 0.0349(4) Uani 1 1 d . . .
H14A H 0.4179 0.9305 0.6261 0.052 Uiso 1 1 calc R U .
H14B H 0.3080 0.9398 0.6598 0.052 Uiso 1 1 calc R U .
H14C H 0.3446 1.0510 0.5510 0.052 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 0.0033 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
C1 O2 C11 107.74(16) . .
C2 C1 O2 128.5(2) . .
C2 C1 C10 121.8(2) . .
O2 C1 C10 109.75(18) . .
C1 C2 C3 115.4(2) . .
C4 C3 C2 124.0(2) . .
C3 C4 C5 120.0(2) . .
C10 C5 C6 113.59(19) . .
C10 C5 C4 115.6(2) . .
C6 C5 C4 130.8(2) . .
C7 C6 C5 120.9(2) . .
C6 C7 C8 124.9(2) . .
C9 C8 C7 114.68(18) . .
C9 C8 C12 124.14(19) . .
C7 C8 C12 121.18(18) . .
C8 C9 C10 119.48(19) . .
C8 C9 C11 136.21(19) . .
C10 C9 C11 104.31(17) . .
C1 C10 C5 123.28(19) . .
C1 C10 C9 110.19(19) . .
C5 C10 C9 126.5(2) . .
O5 C11 O2 118.5(2) . .
O5 C11 C9 133.5(2) . .
O2 C11 C9 108.01(17) . .
C13 C12 C14 107.86(12) . .
C13 C12 C14 107.86(12) . 8_575
C14 C12 C14 110.2(2) . 8_575
C13 C12 C8 112.78(19) . .
C14 C12 C8 109.04(11) . .
C14 C12 C8 109.04(11) 8_575 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C1 1.388(3) .
O2 C11 1.403(3) .
O5 C11 1.199(3) .
C1 C2 1.363(3) .
C1 C10 1.389(3) .
C2 C3 1.424(4) .
C3 C4 1.359(4) .
C4 C5 1.425(3) .
C5 C10 1.389(3) .
C5 C6 1.415(3) .
C6 C7 1.375(3) .
C7 C8 1.425(3) .
C8 C9 1.391(3) .
C8 C12 1.540(3) .
C9 C10 1.402(3) .
C9 C11 1.490(3) .
C12 C13 1.523(3) .
C12 C14 1.536(2) .
C12 C14 1.536(2) 8_575
