#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:16:22 +0200 (Mon, 07 Nov 2022) $
#$Revision: 278975 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/77/1567729.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_1567729
loop_
_publ_author_name
'Rai, Pramod'
'Maji, Kakoli'
'Jana, Sayan K.'
'Maji, Biplab'
_publ_section_title
;
 Intermolecular dearomative [4 + 2] cycloaddition of naphthalenes via
 visible-light energy-transfer-catalysis
;
_journal_issue                   42
_journal_name_full               'Chemical Science'
_journal_page_first              12503
_journal_page_last               12510
_journal_paper_doi               10.1039/D2SC04005K
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C22 H19 F O3'
_chemical_formula_sum            'C22 H19 F O3'
_chemical_formula_weight         350.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-14
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-07-14 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.0290(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8641(2)
_cell_length_b                   10.52260(10)
_cell_length_c                   12.11710(10)
_cell_measurement_reflns_used    12932
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      68.0110
_cell_measurement_theta_min      3.2310
_cell_volume                     1722.21(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00   1.00   0.50    0.23    --  -40.33 108.00 126.00  164
  2  ω     21.00  81.00   0.50    0.23    --   40.33-108.00  29.00  120
  3  ω   -152.00 -82.00   0.50    1.01    --  -82.50-108.00  29.00  140
  4  ω    -83.00 -13.00   0.50    1.01    --  -82.50 108.00 126.00  140
  5  ω    103.00 166.00   0.50    1.01    --   96.67 108.00 126.00  126
  6  ω     27.00 108.00   0.50    1.01    --   96.67-108.00  29.00  162
  7  ω    -24.00  35.00   0.50    0.23    --  -40.33  12.00  30.00  118
  8  ω    -43.00  26.00   0.50    0.23    --  -40.33  38.00 150.00  138
  9  ω    -31.00  30.00   0.50    0.23    --  -40.33  25.00  30.00  122
 10  ω   -108.00 -17.00   0.50    0.23    --  -40.33 -64.00  30.00  182
 11  ω     25.00 111.00   0.50    0.23    --   40.33  25.00 150.00  172
 12  ω    -30.00  31.00   0.50    0.23    --   40.33 -25.00  30.00  122
 13  ω    -27.00  64.00   0.50    0.23    --   40.33 -64.00 -90.00  182
 14  ω    -47.00 -15.00   0.50    1.01    --  -82.50  42.00 -90.00   64
 15  ω    -47.00 -15.00   0.50    1.01    --  -82.50  42.00  60.00   64
 16  ω   -150.00 -69.00   0.50    1.01    --  -82.50 -33.00  60.00  162
 17  ω     83.00 164.00   0.50    1.01    --   96.67  33.00-180.00  162
 18  ω     30.00  57.00   0.50    1.01    --   96.67 -50.00  90.00   54
 19  ω     82.00 167.00   0.50    1.01    --   96.67  25.00  30.00  170
 20  ω     29.00  68.00   0.50    1.01    --   96.67 -59.00  30.00   78
 21  ω     30.00  57.00   0.50    1.01    --   96.67 -50.00   0.00   54
 22  ω     80.00 163.00   0.50    1.01    --   96.67  42.00  60.00  166
 23  ω     27.00 127.00   0.50    1.01    --   96.67 -87.00  30.00  200
 24  ω     82.00 167.00   0.50    1.01    --   96.67  25.00 -60.00  170
 25  ω     29.00  83.00   0.50    1.01    --   96.67 -68.00  60.00  108
 26  ω     30.00 109.00   0.50    1.01    --   96.67-117.00 120.00  158
 27  ω     81.00 164.00   0.50    1.01    --   96.67 145.00 -90.00  166
 28  ω     29.00  68.00   0.50    1.01    --   96.67 -59.00-150.00   78
 29  ω     30.00  57.00   0.50    1.01    --   96.67 -50.00  60.00   54
 30  ω     29.00  68.00   0.50    1.01    --   96.67 -59.00  90.00   78
 31  ω     30.00  57.00   0.50    1.01    --   96.67 -50.00-180.00   54
 32  ω     30.00  57.00   0.50    1.01    --   96.67 -50.00 150.00   54
 33  ω   -109.00 -13.00   0.50    0.23    --  -40.33 -77.00 -60.00  192
 34  ω    -78.00   4.00   0.50    0.23    --  -40.33 104.00 -90.00  164
 35  ω   -109.00 -13.00   0.50    0.23    --  -40.33 -77.00   0.00  192
 36  ω   -109.00 -13.00   0.50    0.23    --  -40.33 -77.00-120.00  192
 37  ω    -31.00  30.00   0.50    0.23    --  -40.33  25.00  90.00  122
 38  ω   -108.00 -17.00   0.50    0.23    --  -40.33 -64.00 120.00  182
 39  ω   -109.00 -13.00   0.50    0.23    --  -40.33 -77.00  90.00  192
 40  ω     21.00 107.00   0.50    0.23    --   40.33  50.00-120.00  172
 41  ω     14.00 109.00   0.50    0.23    --   40.33  77.00-120.00  190
 42  ω     17.00 108.00   0.50    0.23    --   40.33  64.00 -30.00  182
 43  ω     22.00 106.00   0.50    1.01    --   96.67 -96.00-150.00  168
 44  ω     78.00 163.00   0.50    1.01    --   96.67  50.00 120.00  170
 45  ω     83.00 164.00   0.50    1.01    --   96.67  33.00-120.00  162
 46  ω     30.00  57.00   0.50    1.01    --   96.67 -50.00-120.00   54
 47  ω     30.00  57.00   0.50    1.01    --   96.67 -50.00 -90.00   54
 48  ω     75.00 148.00   0.50    1.01    --   96.67  59.00 -30.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1032743000
_diffrn_orient_matrix_UB_12      0.0289310000
_diffrn_orient_matrix_UB_13      0.0211058000
_diffrn_orient_matrix_UB_21      0.0095339000
_diffrn_orient_matrix_UB_22      0.1391859000
_diffrn_orient_matrix_UB_23      -0.0354439000
_diffrn_orient_matrix_UB_31      -0.0474714000
_diffrn_orient_matrix_UB_32      -0.0349621000
_diffrn_orient_matrix_UB_33      -0.1238168000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_min         3.272
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0402
_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)+(0.0517P)²+0.6784P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2862
_reflns_number_total             3149
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04005k2.cif
_cod_data_source_block           kmc-ke257_2_auto_2
_cod_depositor_comments
'Adding full bibliography for 1567725--1567729.cif.'
_cod_database_code               1567729
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O F'
_chemical_oxdiff_usercomment     100K
_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   0.977
_shelx_estimated_absorpt_t_min   0.925
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C8(H8), C22(H22), C10(H10), C9(H9), C18(H18), C19(H19),
 C21(H21)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.850
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
F1 F 0.49734(7) 0.81032(10) 0.64546(8) 0.0391(3) Uani 1 1 d . . . . .
O2 O 0.71444(7) 0.45587(9) 0.11975(8) 0.0236(2) Uani 1 1 d . . . . .
O3 O 0.86712(8) 0.45555(10) 0.08264(8) 0.0297(3) Uani 1 1 d . . . . .
O1 O 0.78639(9) 0.20488(10) 0.14912(9) 0.0342(3) Uani 1 1 d . . . . .
C7 C 0.79801(10) 0.59302(13) 0.27643(11) 0.0211(3) Uani 1 1 d . . . . .
C12 C 0.83273(10) 0.60213(13) 0.39396(11) 0.0216(3) Uani 1 1 d . . . . .
C17 C 0.64387(10) 0.55617(14) 0.48120(12) 0.0232(3) Uani 1 1 d . . . . .
C5 C 0.77878(11) 0.45082(13) 0.05032(12) 0.0238(3) Uani 1 1 d . . . . .
C4 C 0.75380(10) 0.46379(13) 0.23996(11) 0.0214(3) Uani 1 1 d . . . . .
C3 C 0.82715(10) 0.35959(13) 0.29246(12) 0.0226(3) Uani 1 1 d . . . . .
C11 C 0.87432(10) 0.71420(14) 0.44263(12) 0.0235(3) Uani 1 1 d . . . . .
H11 H 0.899614 0.719357 0.522178 0.028 Uiso 1 1 calc R . . . .
C15 C 0.66345(10) 0.44913(14) 0.29485(12) 0.0228(3) Uani 1 1 d . . . . .
H15A H 0.631399 0.365764 0.274046 0.027 Uiso 1 1 calc R . . . .
H15B H 0.614341 0.516587 0.266483 0.027 Uiso 1 1 calc R . . . .
C13 C 0.81429(10) 0.48362(13) 0.45546(11) 0.0225(3) Uani 1 1 d . . . . .
H13 H 0.841500 0.490577 0.538996 0.027 Uiso 1 1 calc R . . . .
C14 C 0.85780(10) 0.37287(13) 0.40507(12) 0.0229(3) Uani 1 1 d . . . . .
H14 H 0.903855 0.316159 0.449902 0.028 Uiso 1 1 calc R . . . .
C8 C 0.79820(10) 0.69908(14) 0.20882(12) 0.0236(3) Uani 1 1 d . . . . .
H8 H 0.771040 0.694823 0.129586 0.028 Uiso 1 1 calc R . . . .
C22 C 0.62256(11) 0.52623(14) 0.58528(12) 0.0257(3) Uani 1 1 d . . . . .
H22 H 0.641914 0.445844 0.618703 0.031 Uiso 1 1 calc R . . . .
C2 C 0.84545(11) 0.24169(14) 0.23343(12) 0.0249(3) Uani 1 1 d . . . . .
C16 C 0.69840(10) 0.45903(13) 0.42575(11) 0.0226(3) Uani 1 1 d . . . . .
H16 H 0.687233 0.374070 0.457680 0.027 Uiso 1 1 calc R . . . .
C10 C 0.87876(11) 0.81897(14) 0.37433(13) 0.0265(3) Uani 1 1 d . . . . .
H10 H 0.909151 0.895314 0.406742 0.032 Uiso 1 1 calc R . . . .
C9 C 0.83875(11) 0.81213(14) 0.25854(12) 0.0266(3) Uani 1 1 d . . . . .
H9 H 0.839039 0.885357 0.212755 0.032 Uiso 1 1 calc R . . . .
C18 C 0.61468(11) 0.67490(14) 0.43388(12) 0.0275(3) Uani 1 1 d . . . . .
H18 H 0.629333 0.697468 0.363518 0.033 Uiso 1 1 calc R . . . .
C20 C 0.54577(11) 0.72615(16) 0.59094(13) 0.0293(3) Uani 1 1 d . . . . .
C19 C 0.56444(11) 0.76085(15) 0.48807(13) 0.0302(3) Uani 1 1 d . . . . .
H19 H 0.543668 0.841023 0.455098 0.036 Uiso 1 1 calc R . . . .
C21 C 0.57380(11) 0.61118(16) 0.64090(12) 0.0287(3) Uani 1 1 d . . . . .
H21 H 0.560107 0.590212 0.712084 0.034 Uiso 1 1 calc R . . . .
C6 C 0.72237(12) 0.43965(15) -0.07025(12) 0.0283(3) Uani 1 1 d . . . . .
H6A H 0.673022 0.371792 -0.076400 0.042 Uiso 1 1 calc GR . . . .
H6B H 0.768243 0.419549 -0.118594 0.042 Uiso 1 1 calc GR . . . .
H6C H 0.688936 0.520290 -0.094621 0.042 Uiso 1 1 calc GR . . . .
C1 C 0.93735(12) 0.16685(15) 0.28156(14) 0.0318(4) Uani 1 1 d . . . . .
H1A H 0.938142 0.143187 0.359985 0.048 Uiso 1 1 calc GR . . . .
H1B H 0.995748 0.218616 0.279825 0.048 Uiso 1 1 calc GR . . . .
H1C H 0.938219 0.089822 0.236330 0.048 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C5 O2 C4 118.52(11) . . ?
C12 C7 C4 112.43(12) . . ?
C8 C7 C12 120.04(13) . . ?
C8 C7 C4 127.23(12) . . ?
C7 C12 C13 112.92(12) . . ?
C11 C12 C7 120.41(13) . . ?
C11 C12 C13 126.59(12) . . ?
C22 C17 C16 118.50(13) . . ?
C22 C17 C18 118.21(13) . . ?
C18 C17 C16 123.29(12) . . ?
O2 C5 C6 109.61(12) . . ?
O3 C5 O2 124.12(13) . . ?
O3 C5 C6 126.27(13) . . ?
O2 C4 C7 112.54(11) . . ?
O2 C4 C3 116.34(11) . . ?
O2 C4 C15 105.64(10) . . ?
C7 C4 C3 109.50(11) . . ?
C7 C4 C15 106.05(11) . . ?
C3 C4 C15 105.96(11) . . ?
C14 C3 C4 112.08(12) . . ?
C14 C3 C2 121.90(13) . . ?
C2 C3 C4 124.63(12) . . ?
C12 C11 C10 119.51(13) . . ?
C4 C15 C16 109.55(11) . . ?
C12 C13 C16 107.42(11) . . ?
C14 C13 C12 108.23(11) . . ?
C14 C13 C16 105.06(11) . . ?
C3 C14 C13 115.44(13) . . ?
C7 C8 C9 119.12(13) . . ?
C21 C22 C17 121.38(14) . . ?
O1 C2 C3 120.96(14) . . ?
O1 C2 C1 120.68(13) . . ?
C3 C2 C1 118.35(12) . . ?
C17 C16 C15 115.20(12) . . ?
C17 C16 C13 111.73(11) . . ?
C15 C16 C13 108.02(11) . . ?
C11 C10 C9 119.98(13) . . ?
C10 C9 C8 120.74(13) . . ?
C19 C18 C17 121.12(14) . . ?
F1 C20 C19 118.55(14) . . ?
F1 C20 C21 118.67(13) . . ?
C21 C20 C19 122.78(14) . . ?
C20 C19 C18 118.05(14) . . ?
C20 C21 C22 118.45(14) . . ?
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
F1 C20 1.3680(17) . ?
O2 C5 1.3582(17) . ?
O2 C4 1.4381(16) . ?
O3 C5 1.1999(18) . ?
O1 C2 1.2195(18) . ?
C7 C12 1.4000(19) . ?
C7 C4 1.5159(19) . ?
C7 C8 1.385(2) . ?
C12 C11 1.385(2) . ?
C12 C13 1.5038(19) . ?
C17 C22 1.395(2) . ?
C17 C16 1.516(2) . ?
C17 C18 1.396(2) . ?
C5 C6 1.498(2) . ?
C4 C3 1.533(2) . ?
C4 C15 1.5526(19) . ?
C3 C14 1.342(2) . ?
C3 C2 1.482(2) . ?
C11 C10 1.388(2) . ?
C15 C16 1.5539(18) . ?
C13 C14 1.5037(19) . ?
C13 C16 1.587(2) . ?
C8 C9 1.393(2) . ?
C22 C21 1.384(2) . ?
C2 C1 1.500(2) . ?
C10 C9 1.389(2) . ?
C18 C19 1.393(2) . ?
C20 C19 1.378(2) . ?
C20 C21 1.369(2) . ?
