#------------------------------------------------------------------------------
#$Date: 2019-11-24 08:19:22 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237270 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/44/1554484.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_1554484
loop_
_publ_author_name
'Han, Sang Hoon'
'Pandey, Ashok Kumar'
'Lee, Heeyoung'
'Kim, Saegun'
'Kang, Dahye'
'Jung, Young Hoon'
'Kim, Hyung Sik'
'Hong, Sungwoo'
'Kim, In Su'
_publ_section_title
;
 One-pot synthesis of 2-naphthols from nitrones and MBH adducts via
 decarboxylative N--O bond cleavage
;
_journal_issue                   22
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3210
_journal_paper_doi               10.1039/C8QO00988K
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C11 H9 F O2'
_chemical_formula_weight         192.18
_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
_audit_creation_method           'APEX2 v2014.1-1'
_audit_update_record
;
2018-07-26 deposited with the CCDC.
2018-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9693(3)
_cell_length_b                   5.8579(3)
_cell_length_c                   31.3863(17)
_cell_measurement_reflns_used    7005
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.54
_cell_measurement_theta_min      2.60
_cell_volume                     913.64(9)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2014.5.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0540
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            29989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.759
_diffrn_reflns_theta_min         2.596
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
; 
 Flack x determined using 605 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.5(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0506
_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)+(0.0397P)²+0.2050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1060
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1864
_reflns_number_total             2375
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qo00988k2.cif
_cod_data_source_block           global
_cod_database_code               1554484
_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   0.980
_shelx_estimated_absorpt_t_max   0.995
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, 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
C1 C 0.2684(6) 0.4479(4) 0.14537(9) 0.0481(6) Uani 1 1 d . .
C2 C 0.0966(6) 0.4193(4) 0.17800(9) 0.0500(7) Uani 1 1 d . .
H2 H 0.0901 0.5245 0.2002 0.060 Uiso 1 1 calc R U
C3 C -0.0734(5) 0.2270(4) 0.17793(8) 0.0452(6) Uani 1 1 d . .
C4 C -0.0682(5) 0.0753(4) 0.14466(7) 0.0412(6) Uani 1 1 d . .
H4 H -0.1823 -0.0506 0.1448 0.049 Uiso 1 1 calc R U
C5 C 0.1106(5) 0.1100(4) 0.11015(8) 0.0363(5) Uani 1 1 d . .
C6 C 0.1219(5) -0.0435(4) 0.07521(7) 0.0401(5) Uani 1 1 d . .
H6 H 0.0075 -0.1692 0.0744 0.048 Uiso 1 1 calc R U
C7 C 0.3000(5) -0.0074(4) 0.04273(7) 0.0401(6) Uani 1 1 d . .
C8 C 0.4777(5) 0.1784(5) 0.04318(8) 0.0490(7) Uani 1 1 d . .
H8 H 0.6000 0.1984 0.0211 0.059 Uiso 1 1 calc R U
C9 C 0.4706(5) 0.3297(5) 0.07619(9) 0.0499(7) Uani 1 1 d . .
H9 H 0.5879 0.4534 0.0764 0.060 Uiso 1 1 calc R U
C10 C 0.2871(5) 0.3005(4) 0.11003(8) 0.0408(5) Uani 1 1 d . .
C11 C -0.4045(7) 0.0136(5) 0.21546(9) 0.0596(8) Uani 1 1 d . .
H11A H -0.5239 0.0124 0.1914 0.089 Uiso 1 1 calc R U
H11B H -0.5078 0.0195 0.2413 0.089 Uiso 1 1 calc R U
H11C H -0.2968 -0.1224 0.2153 0.089 Uiso 1 1 calc R U
F1 F 0.4397(4) 0.6295(3) 0.14581(6) 0.0725(6) Uani 1 1 d . .
O1 O -0.2340(4) 0.2084(4) 0.21311(6) 0.0582(5) Uani 1 1 d . .
O2 O 0.3180(4) -0.1498(3) 0.00781(6) 0.0533(5) Uani 1 1 d . .
H2A H 0.1735 -0.2146 0.0042 0.080 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'
F F 0.0171 0.0103 '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
C2 C1 F1 119.1(2)
C2 C1 C10 124.4(2)
F1 C1 C10 116.4(2)
C1 C2 C3 118.7(2)
C1 C2 H2 120.7
C3 C2 H2 120.7
O1 C3 C4 125.0(2)
O1 C3 C2 114.4(2)
C4 C3 C2 120.6(2)
C3 C4 C5 120.1(2)
C3 C4 H4 120.0
C5 C4 H4 120.0
C4 C5 C10 120.2(2)
C4 C5 C6 121.6(2)
C10 C5 C6 118.2(2)
C7 C6 C5 120.2(2)
C7 C6 H6 119.9
C5 C6 H6 119.9
C6 C7 O2 122.7(2)
C6 C7 C8 121.4(2)
O2 C7 C8 115.9(2)
C9 C8 C7 119.7(2)
C9 C8 H8 120.1
C7 C8 H8 120.1
C8 C9 C10 120.6(2)
C8 C9 H9 119.7
C10 C9 H9 119.7
C1 C10 C9 124.1(2)
C1 C10 C5 116.0(2)
C9 C10 C5 119.8(2)
O1 C11 H11A 109.5
O1 C11 H11B 109.5
H11A C11 H11B 109.5
O1 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C3 O1 C11 116.97(19)
C7 O2 H2A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.344(4)
C1 F1 1.362(3)
C1 C10 1.409(4)
C2 C3 1.408(4)
C2 H2 0.9300
C3 O1 1.367(3)
C3 C4 1.371(3)
C4 C5 1.416(3)
C4 H4 0.9300
C5 C10 1.419(3)
C5 C6 1.419(3)
C6 C7 1.367(3)
C6 H6 0.9300
C7 O2 1.380(3)
C7 C8 1.401(3)
C8 C9 1.364(4)
C8 H8 0.9300
C9 C10 1.410(4)
C9 H9 0.9300
C11 O1 1.423(3)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
O2 H2A 0.8200
