#------------------------------------------------------------------------------
#$Date: 2022-04-21 01:14:58 +0300 (Thu, 21 Apr 2022) $
#$Revision: 274607 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/68/1566844.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_1566844
loop_
_publ_author_name
'Owatari, Yoshihiro'
'Iseki, Shuta'
'Ogata, Daiji'
'Yuasa, Junpei'
_publ_section_title
;
 Catalytic electron drives host--guest recognition
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC01342H
_journal_year                    2022
_chemical_formula_sum            'C16 H11 N O2'
_chemical_formula_weight         249.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_Hall           'C 2c -2'
_space_group_name_H-M_alt        'C m c 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-07-13 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.732(9)
_cell_length_b                   10.702(7)
_cell_length_c                   7.661(5)
_cell_measurement_reflns_used    2078
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      2.35
_cell_volume                     1207.8(13)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2078
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         2.352
_exptl_absorpt_coefficient_mu    0.091
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 406 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_coef       0.020(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         1037
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0466
_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+0.4619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1485
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.884
_reflns_Friedel_fraction_max     0.884
_reflns_number_gt                984
_reflns_number_total             1037
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc01342h3.cif
_cod_data_source_block           CNAntr_0maa_aa_a
_cod_original_cell_volume        1208.0(13)
_cod_database_code               1566844
_shelx_shelxl_version_number     2016/6
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.500000 0.1558(3) 0.8092(5) 0.0364(9) Uani 1 2 d S T P . .
O002 O 0.500000 0.5813(3) 0.4400(6) 0.0674(15) Uani 1 2 d S T P . .
C1 C 0.500000 0.2185(4) 0.6463(5) 0.0254(10) Uani 1 2 d S T P . .
C004 C 0.5861(2) 0.2932(3) 0.6199(4) 0.0289(8) Uani 1 1 d . . . . .
N005 N 0.500000 0.1862(5) 0.1915(7) 0.0517(13) Uani 1 2 d S T P . .
C006 C 0.500000 0.1511(3) 0.3326(6) 0.0310(11) Uani 1 2 d S T P . .
C007 C 0.5860(2) 0.4112(3) 0.5436(4) 0.0361(9) Uani 1 1 d . . . . .
C008 C 0.500000 0.1083(4) 0.5130(6) 0.0298(10) Uani 1 2 d S T P . .
H00A H 0.553210 0.056861 0.532741 0.036 Uiso 0.5 1 calc R U P . .
H00B H 0.446790 0.056861 0.532741 0.036 Uiso 0.5 1 calc R U P . .
C009 C 0.500000 0.4757(4) 0.5008(6) 0.0396(13) Uani 1 2 d S T P . .
C00A C 0.6682(2) 0.2385(4) 0.6671(5) 0.0458(11) Uani 1 1 d . . . . .
H00C H 0.668919 0.160131 0.719506 0.055 Uiso 1 1 calc R U . . .
C00B C 0.6687(4) 0.4720(4) 0.5130(6) 0.0639(15) Uani 1 1 d . . . . .
H00D H 0.669011 0.551010 0.462498 0.077 Uiso 1 1 calc R U . . .
C00C C 0.7499(3) 0.3019(6) 0.6353(7) 0.0743(18) Uani 1 1 d . . . . .
H00E H 0.804842 0.265920 0.667777 0.089 Uiso 1 1 calc R U . . .
C00D C 0.7488(3) 0.4162(6) 0.5568(8) 0.083(2) Uani 1 1 d . . . . .
H00F H 0.803238 0.456563 0.532755 0.100 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'
N N 0.0061 0.0033 '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
O001 C1 C004 111.6(2) . 4_655 ?
O001 C1 C004 111.6(2) . . ?
C004 C1 C004 114.0(4) 4_655 . ?
O001 C1 C008 102.7(3) . . ?
C004 C1 C008 108.2(2) 4_655 . ?
C004 C1 C008 108.2(2) . . ?
C007 C004 C00A 119.5(3) . . ?
C007 C004 C1 122.3(3) . . ?
C00A C004 C1 118.2(3) . . ?
N005 C006 C008 179.2(4) . . ?
C004 C007 C00B 119.4(4) . . ?
C004 C007 C009 121.2(3) . . ?
C00B C007 C009 119.4(4) . . ?
C006 C008 C1 112.6(3) . . ?
C006 C008 H00A 109.1 . . ?
C1 C008 H00A 109.1 . . ?
C006 C008 H00B 109.1 . . ?
C1 C008 H00B 109.1 . . ?
H00A C008 H00B 107.8 . . ?
O002 C009 C007 121.06(18) . . ?
O002 C009 C007 121.06(18) . 4_655 ?
C007 C009 C007 117.8(4) . 4_655 ?
C004 C00A C00C 119.8(4) . . ?
C004 C00A H00C 120.1 . . ?
C00C C00A H00C 120.1 . . ?
C00D C00B C007 120.5(4) . . ?
C00D C00B H00D 119.8 . . ?
C007 C00B H00D 119.8 . . ?
C00D C00C C00A 120.0(5) . . ?
C00D C00C H00E 120.0 . . ?
C00A C00C H00E 120.0 . . ?
C00C C00D C00B 120.8(4) . . ?
C00C C00D H00F 119.6 . . ?
C00B C00D H00F 119.6 . . ?
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 C1 1.417(5) . ?
O002 C009 1.223(6) . ?
C1 C004 1.513(4) 4_655 ?
C1 C004 1.513(4) . ?
C1 C008 1.560(5) . ?
C004 C007 1.392(5) . ?
C004 C00A 1.391(5) . ?
N005 C006 1.144(7) . ?
C006 C008 1.456(6) . ?
C007 C00B 1.401(5) . ?
C007 C009 1.479(4) . ?
C008 H00A 0.9700 . ?
C008 H00B 0.9700 . ?
C00A C00C 1.403(6) . ?
C00A H00C 0.9300 . ?
C00B C00D 1.364(8) . ?
C00B H00D 0.9300 . ?
C00C C00D 1.363(9) . ?
C00C H00E 0.9300 . ?
C00D H00F 0.9300 . ?
