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#$Date: 2023-09-01 00:58:41 +0300 (Fri, 01 Sep 2023) $
#$Revision: 285931 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/20/7132076.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_7132076
loop_
_publ_author_name
'Wei, Qing-Yi'
'Zhou, Ze'
'Yao, Meng-Lian'
'Liu, Jikai'
'Wu, Bin'
'Yang, Jin-Ming'
_publ_section_title
;
 Rhodium(III)-Catalyzed Intermolecular [3+3] Annulation of Benzoxazines
 with Quinone Compounds: Access to Spiro-Heterocyclic Scaffolds
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03609J
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H14 Br N O3'
_chemical_formula_sum            'C20 H14 Br N O3'
_chemical_formula_weight         396.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-16
_audit_creation_method
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) 
;
_audit_update_record
;
2023-05-10 deposited with the CCDC.	2023-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1673(15)
_cell_length_b                   15.976(4)
_cell_length_c                   16.479(4)
_cell_measurement_reflns_used    8979
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      70.20
_cell_measurement_theta_min      3.35
_cell_volume                     1623.7(7)
_computing_cell_refinement
'SAINT V8.40B Bruker-AXS, Madison WI for PHOTON III'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction
'SAINT V8.40B Bruker-AXS, Madison WI for PHOTON III'
_computing_molecular_graphics
'Bruker SHELXTL Bruker-AXS, Madison WI and local programs'
_computing_publication_material  'Bruker SHELXTL Bruker-AXS, Madison WI'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon III 28 detector'
_diffrn_detector_area_resol_mean ' 7.39 for PHOTON III'
_diffrn_detector_type            'Bruker Photon III 28'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker Photon III'
_diffrn_measurement_method       'Profile data from θ/2θ scans'
_diffrn_radiation_monochromator  'Metaljet Helios MX'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_xray_symbol    'Ga K\a'
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24321
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         70.461
_diffrn_reflns_theta_min         3.352
_diffrn_source                   'METALJET liquid metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_target            Ga
_diffrn_source_type              'Sealed X-ray tube'
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.385
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.5418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 - Bruker AXS, Madison WI for PHOTON III'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.879
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
; 
 Flack x determined using 1714 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.013(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0403
_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)+(0.0461P)²+0.7207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                4390
_reflns_number_total             4582
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc03609j2.cif
_cod_data_source_block           221220e_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_cell_volume        1623.6(7)
_cod_database_code               7132076
_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   0.796
_shelx_estimated_absorpt_t_min   0.763
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All N(H) groups 
 At 1.5 times of: 
  All O(H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 C7(H7A,H7B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C2(H2), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C17(H17), 
 C18(H18), C20(H20), N1(H1) 
2.c Idealised tetrahedral OH refined as rotating group: 
 O3(H3) 
;
_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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
Br1 Br -0.38210(7) 0.72827(2) 0.34262(2) 0.03270(12) Uani 1 1 d . . . . .
C1 C -0.1513(6) 0.66062(18) 0.38065(19) 0.0259(6) Uani 1 1 d . . . . .
C2 C -0.0498(6) 0.60736(18) 0.32573(17) 0.0248(6) Uani 1 1 d . . . . .
H2 H -0.091257 0.607749 0.270205 0.030 Uiso 1 1 calc R U . . .
C3 C 0.1137(6) 0.55313(16) 0.35258(17) 0.0231(5) Uani 1 1 d . . . . .
C4 C 0.1737(6) 0.55618(17) 0.43451(18) 0.0232(6) Uani 1 1 d . . . . .
C5 C 0.0741(6) 0.61035(19) 0.48817(18) 0.0289(7) Uani 1 1 d . . . . .
H5 H 0.119213 0.611722 0.543278 0.035 Uiso 1 1 calc R U . . .
C6 C -0.0919(7) 0.6630(2) 0.46211(19) 0.0297(7) Uani 1 1 d . . . . .
H6 H -0.162856 0.699551 0.499003 0.036 Uiso 1 1 calc R U . . .
C7 C 0.4938(6) 0.48436(19) 0.40122(18) 0.0248(6) Uani 1 1 d . . . . .
H7A H 0.602735 0.445086 0.423516 0.030 Uiso 1 1 calc R U . . .
H7B H 0.569782 0.536484 0.385524 0.030 Uiso 1 1 calc R U . . .
C8 C 0.3880(7) 0.44533(17) 0.32581(17) 0.0244(6) Uani 1 1 d . . . . .
C9 C 0.5565(6) 0.43315(19) 0.25974(18) 0.0245(6) Uani 1 1 d . . . . .
C10 C 0.5884(7) 0.49296(19) 0.19949(19) 0.0291(7) Uani 1 1 d . . . . .
H10 H 0.500204 0.541675 0.197864 0.035 Uiso 1 1 calc R U . . .
C11 C 0.7509(7) 0.4811(2) 0.1413(2) 0.0322(7) Uani 1 1 d . . . . .
H11 H 0.772603 0.521890 0.100148 0.039 Uiso 1 1 calc R U . . .
C12 C 0.8804(7) 0.4101(2) 0.14333(18) 0.0317(7) Uani 1 1 d . . . . .
H12 H 0.990615 0.402337 0.103746 0.038 Uiso 1 1 calc R U . . .
C13 C 0.8484(6) 0.3503(2) 0.20355(19) 0.0285(7) Uani 1 1 d . . . . .
H13 H 0.935881 0.301333 0.204349 0.034 Uiso 1 1 calc R U . . .
C14 C 0.6882(6) 0.36143(18) 0.26318(18) 0.0228(6) Uani 1 1 d . . . . .
C15 C 0.6412(6) 0.29874(17) 0.32593(16) 0.0230(6) Uani 1 1 d . . . . .
C16 C 0.4402(6) 0.30170(18) 0.36496(17) 0.0228(6) Uani 1 1 d . . . . .
C17 C 0.3759(6) 0.23875(18) 0.41779(17) 0.0264(6) Uani 1 1 d . . . . .
H17 H 0.237209 0.240465 0.442808 0.032 Uiso 1 1 calc R U . . .
C18 C 0.5189(6) 0.17269(18) 0.43358(18) 0.0264(6) Uani 1 1 d . . . . .
H18 H 0.476521 0.129053 0.469391 0.032 Uiso 1 1 calc R U . . .
C19 C 0.7214(6) 0.17034(19) 0.39753(19) 0.0270(6) Uani 1 1 d . . . . .
C20 C 0.7845(6) 0.23311(18) 0.34390(19) 0.0266(6) Uani 1 1 d . . . . .
H20 H 0.924142 0.231513 0.319581 0.032 Uiso 1 1 calc R U . . .
N1 N 0.2165(6) 0.49816(17) 0.29998(16) 0.0280(6) Uani 1 1 d . . . . .
H1 H 0.173928 0.495984 0.249046 0.034 Uiso 1 1 calc R U . . .
O1 O 0.3353(4) 0.50300(13) 0.46264(13) 0.0257(5) Uani 1 1 d . . . . .
O2 O 0.2921(4) 0.36492(12) 0.34873(15) 0.0258(4) Uani 1 1 d . . . . .
O3 O 0.8704(5) 0.10779(16) 0.41114(16) 0.0393(6) Uani 1 1 d . . . . .
H3 H 0.819428 0.073272 0.444523 0.059 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 0.0137 0.0067 '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'
Br Br -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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
C2 C1 Br1 118.2(2) . . ?
C2 C1 C6 121.7(3) . . ?
C6 C1 Br1 120.1(3) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 118.2(3) . . ?
N1 C3 C2 121.5(3) . . ?
N1 C3 C4 120.2(3) . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 O1 119.2(3) . . ?
O1 C4 C3 119.3(3) . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.3(3) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
O1 C7 H7A 109.4 . . ?
O1 C7 H7B 109.4 . . ?
O1 C7 C8 111.4(3) . . ?
C9 C8 C7 110.0(3) . . ?
N1 C8 C7 108.5(2) . . ?
N1 C8 C9 111.8(2) . . ?
N1 C8 O2 107.4(3) . . ?
O2 C8 C7 108.6(2) . . ?
O2 C8 C9 110.4(2) . . ?
C10 C9 C8 121.4(3) . . ?
C10 C9 C14 120.4(3) . . ?
C14 C9 C8 118.1(3) . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.8(3) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 C15 118.1(3) . . ?
C13 C14 C9 118.8(3) . . ?
C13 C14 C15 123.0(3) . . ?
C16 C15 C14 118.4(3) . . ?
C16 C15 C20 119.1(3) . . ?
C20 C15 C14 122.3(3) . . ?
C17 C16 C15 121.2(3) . . ?
O2 C16 C15 121.3(3) . . ?
O2 C16 C17 117.4(3) . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.9(3) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C20 120.4(3) . . ?
O3 C19 C18 123.5(3) . . ?
O3 C19 C20 116.1(3) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 C15 119.7(3) . . ?
C19 C20 H20 120.1 . . ?
C3 N1 C8 122.0(2) . . ?
C3 N1 H1 119.0 . . ?
C8 N1 H1 119.0 . . ?
C4 O1 C7 112.3(2) . . ?
C16 O2 C8 115.0(3) . . ?
C19 O3 H3 109.5 . . ?
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
Br1 C1 1.894(3) . ?
C1 C2 1.391(4) . ?
C1 C6 1.392(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(5) . ?
C3 C4 1.401(4) . ?
C3 N1 1.387(4) . ?
C4 C5 1.382(4) . ?
C4 O1 1.389(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(5) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.536(4) . ?
C7 O1 1.438(4) . ?
C8 C9 1.518(5) . ?
C8 N1 1.419(4) . ?
C8 O2 1.464(4) . ?
C9 C10 1.392(4) . ?
C9 C14 1.405(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.400(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.405(5) . ?
C14 C15 1.468(4) . ?
C15 C16 1.397(5) . ?
C15 C20 1.403(4) . ?
C16 C17 1.388(4) . ?
C16 O2 1.388(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.400(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(5) . ?
C19 C20 1.392(4) . ?
C19 O3 1.376(4) . ?
C20 H20 0.9500 . ?
N1 H1 0.8800 . ?
O3 H3 0.8400 . ?
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
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O1 0.84 1.96 2.740(3) 154.3 2_556 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C3 -176.6(2) . . . . ?
Br1 C1 C6 C5 178.0(3) . . . . ?
C1 C2 C3 C4 -1.7(5) . . . . ?
C1 C2 C3 N1 179.0(3) . . . . ?
C2 C1 C6 C5 0.2(5) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C2 C3 C4 O1 179.9(3) . . . . ?
C2 C3 N1 C8 177.5(3) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C3 C4 O1 C7 31.0(4) . . . . ?
C4 C3 N1 C8 -1.9(5) . . . . ?
C4 C5 C6 C1 -1.2(5) . . . . ?
C5 C4 O1 C7 -149.7(3) . . . . ?
C6 C1 C2 C3 1.3(5) . . . . ?
C7 C8 C9 C10 -94.3(4) . . . . ?
C7 C8 C9 C14 82.5(3) . . . . ?
C7 C8 N1 C3 -23.6(4) . . . . ?
C7 C8 O2 C16 -71.3(3) . . . . ?
C8 C7 O1 C4 -57.4(3) . . . . ?
C8 C9 C10 C11 177.6(3) . . . . ?
C8 C9 C14 C13 -178.5(3) . . . . ?
C8 C9 C14 C15 5.7(4) . . . . ?
C9 C8 N1 C3 -145.0(3) . . . . ?
C9 C8 O2 C16 49.3(3) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C9 C14 C15 C16 16.1(4) . . . . ?
C9 C14 C15 C20 -168.3(3) . . . . ?
C10 C9 C14 C13 -1.6(5) . . . . ?
C10 C9 C14 C15 -177.5(3) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 -0.9(5) . . . . ?
C12 C13 C14 C9 1.7(5) . . . . ?
C12 C13 C14 C15 177.3(3) . . . . ?
C13 C14 C15 C16 -159.5(3) . . . . ?
C13 C14 C15 C20 16.1(5) . . . . ?
C14 C9 C10 C11 0.8(5) . . . . ?
C14 C15 C16 C17 172.4(3) . . . . ?
C14 C15 C16 O2 -3.7(4) . . . . ?
C14 C15 C20 C19 -172.9(3) . . . . ?
C15 C16 C17 C18 1.9(4) . . . . ?
C15 C16 O2 C8 -30.5(4) . . . . ?
C16 C15 C20 C19 2.6(5) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
C17 C16 O2 C8 153.3(3) . . . . ?
C17 C18 C19 C20 -1.0(5) . . . . ?
C17 C18 C19 O3 179.2(3) . . . . ?
C18 C19 C20 C15 -0.5(5) . . . . ?
C20 C15 C16 C17 -3.4(4) . . . . ?
C20 C15 C16 O2 -179.4(3) . . . . ?
N1 C3 C4 C5 180.0(3) . . . . ?
N1 C3 C4 O1 -0.7(5) . . . . ?
N1 C8 C9 C10 26.3(4) . . . . ?
N1 C8 C9 C14 -156.8(3) . . . . ?
N1 C8 O2 C16 171.5(2) . . . . ?
O1 C4 C5 C6 -178.5(3) . . . . ?
O1 C7 C8 C9 175.3(2) . . . . ?
O1 C7 C8 N1 52.7(3) . . . . ?
O1 C7 C8 O2 -63.7(3) . . . . ?
O2 C8 C9 C10 145.8(3) . . . . ?
O2 C8 C9 C14 -37.3(4) . . . . ?
O2 C8 N1 C3 93.7(3) . . . . ?
O2 C16 C17 C18 178.1(3) . . . . ?
O3 C19 C20 C15 179.3(3) . . . . ?
