#------------------------------------------------------------------------------
#$Date: 2020-07-07 03:59:40 +0300 (Tue, 07 Jul 2020) $
#$Revision: 254040 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/85/1558509.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_1558509
loop_
_publ_author_name
'Wu, An'
'Qian, Hui'
'Zhao, Wanxiang'
'Sun, Jianwei'
_publ_section_title
;
 Benzannulation of Isobenzopyryliums with Electron-Rich Alkynes: A Modular
 Access to β-Functionalized Naphthalenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02502J
_journal_year                    2020
_chemical_formula_moiety         'C15 H15 F O2'
_chemical_formula_sum            'C15 H15 F O2'
_chemical_formula_weight         246.27
_chemical_name_systematic        3-Butyl-7-fluoro-2-hydroxy-1-naphthaldehyde
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-14
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2020-04-09 deposited with the CCDC.	2020-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.872(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.37471(14)
_cell_length_b                   19.0645(3)
_cell_length_c                   9.32895(18)
_cell_measurement_reflns_used    2687
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.3120
_cell_measurement_theta_min      5.6040
_cell_volume                     1217.19(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   33.00   76.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  150.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega   87.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000  -60.0000 91

#__ type_ start__ end____ width___ exp.time_
  3 omega  118.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  111.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
  5 omega   36.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  -90.0000 69

#__ type_ start__ end____ width___ exp.time_
  6 omega   32.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000 -150.0000 81

#__ type_ start__ end____ width___ exp.time_
  7 omega   24.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9453 -125.0000  -90.0000 74

#__ type_ start__ end____ width___ exp.time_
  8 omega -108.00    1.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -19.0000 -120.0000 109
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1640809000
_diffrn_orient_matrix_UB_12      0.0335222000
_diffrn_orient_matrix_UB_13      -0.1382161000
_diffrn_orient_matrix_UB_21      0.0801803000
_diffrn_orient_matrix_UB_22      0.0734493000
_diffrn_orient_matrix_UB_23      0.0593051000
_diffrn_orient_matrix_UB_31      0.1315137000
_diffrn_orient_matrix_UB_32      -0.0028893000
_diffrn_orient_matrix_UB_33      -0.0952124000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0121
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3701
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.975
_diffrn_reflns_theta_min         4.639
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloromethane and hexane'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2115
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0307
_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)+(0.0500P)²+0.2410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1980
_reflns_number_total             2115
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02502j2.cif
_cod_data_source_block           an3cult
_cod_database_code               1558509
_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.
;
_reflns_odcompleteness_completeness 98.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C7(H7), C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-01-13
_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+1/2'
'-x, -y, -z'
'x-1/2, -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 -0.16156(8) 0.65358(3) 0.07805(6) 0.02227(17) Uani 1 1 d . . . . .
O1 O 0.46619(11) 0.69602(4) 0.76406(8) 0.02256(19) Uani 1 1 d . . . . .
O2 O 0.54644(10) 0.56786(4) 0.83671(8) 0.01974(18) Uani 1 1 d . . . . .
H2 H 0.5513 0.6116 0.8478 0.030 Uiso 1 1 calc GR . . . .
C1 C 0.35080(14) 0.67615(5) 0.63641(11) 0.0180(2) Uani 1 1 d . . . . .
H1 H 0.2814 0.7109 0.5637 0.022 Uiso 1 1 calc R . . . .
C2 C 0.31490(13) 0.60340(5) 0.59091(10) 0.0147(2) Uani 1 1 d . . . . .
C3 C 0.41852(14) 0.55157(5) 0.69561(11) 0.0149(2) Uani 1 1 d . . . . .
C4 C 0.39621(14) 0.47868(5) 0.65938(11) 0.0150(2) Uani 1 1 d . . . . .
C5 C 0.26930(14) 0.46083(5) 0.51490(11) 0.0153(2) Uani 1 1 d . . . . .
H5 H 0.2536 0.4125 0.4880 0.018 Uiso 1 1 calc R . . . .
C6 C 0.15954(13) 0.51062(5) 0.40276(11) 0.0151(2) Uani 1 1 d . . . . .
C7 C 0.03110(14) 0.48834(5) 0.25523(11) 0.0167(2) Uani 1 1 d . . . . .
H7 H 0.0192 0.4397 0.2314 0.020 Uiso 1 1 calc R . . . .
C8 C -0.07661(14) 0.53570(5) 0.14580(11) 0.0175(2) Uani 1 1 d . . . . .
H8 H -0.1626 0.5208 0.0466 0.021 Uiso 1 1 calc R . . . .
C9 C -0.05470(14) 0.60651(5) 0.18613(11) 0.0168(2) Uani 1 1 d . . . . .
C10 C 0.06638(14) 0.63157(5) 0.32647(11) 0.0159(2) Uani 1 1 d . . . . .
H10 H 0.0747 0.6805 0.3476 0.019 Uiso 1 1 calc R . . . .
C11 C 0.17908(13) 0.58318(5) 0.43969(10) 0.0140(2) Uani 1 1 d . . . . .
C12 C 0.51298(14) 0.42664(5) 0.78029(11) 0.0166(2) Uani 1 1 d . . . . .
H12A H 0.4785 0.4324 0.8725 0.020 Uiso 1 1 calc R . . . .
H12B H 0.6534 0.4381 0.8113 0.020 Uiso 1 1 calc R . . . .
C13 C 0.48329(14) 0.34994(5) 0.73064(11) 0.0176(2) Uani 1 1 d . . . . .
H13A H 0.3434 0.3378 0.7004 0.021 Uiso 1 1 calc R . . . .
H13B H 0.5186 0.3435 0.6390 0.021 Uiso 1 1 calc R . . . .
C14 C 0.60507(16) 0.30016(6) 0.85768(12) 0.0244(2) Uani 1 1 d . . . . .
H14A H 0.7434 0.3153 0.8962 0.029 Uiso 1 1 calc R . . . .
H14B H 0.5596 0.3025 0.9449 0.029 Uiso 1 1 calc R . . . .
C15 C 0.59117(19) 0.22476(6) 0.80096(16) 0.0341(3) Uani 1 1 d . . . . .
H15A H 0.6450 0.2216 0.7197 0.051 Uiso 1 1 calc GR . . . .
H15B H 0.4540 0.2101 0.7595 0.051 Uiso 1 1 calc GR . . . .
H15C H 0.6656 0.1941 0.8871 0.051 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
O1 C1 C2 124.14(9) . . ?
C3 C2 C1 118.67(9) . . ?
C3 C2 C11 119.52(9) . . ?
C11 C2 C1 121.79(9) . . ?
O2 C3 C2 121.60(9) . . ?
O2 C3 C4 115.84(9) . . ?
C2 C3 C4 122.56(9) . . ?
C3 C4 C12 118.74(9) . . ?
C5 C4 C3 116.92(9) . . ?
C5 C4 C12 124.34(9) . . ?
C4 C5 C6 123.54(9) . . ?
C7 C6 C5 120.46(9) . . ?
C7 C6 C11 119.96(9) . . ?
C11 C6 C5 119.58(9) . . ?
C8 C7 C6 121.22(9) . . ?
C7 C8 C9 117.34(9) . . ?
F1 C9 C8 117.49(8) . . ?
F1 C9 C10 118.08(9) . . ?
C10 C9 C8 124.43(9) . . ?
C9 C10 C11 118.65(9) . . ?
C6 C11 C2 117.86(9) . . ?
C10 C11 C2 123.73(9) . . ?
C10 C11 C6 118.40(9) . . ?
C4 C12 C13 115.23(8) . . ?
C14 C13 C12 112.64(8) . . ?
C15 C14 C13 111.97(9) . . ?
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 C9 1.3605(11) . ?
O1 C1 1.2372(13) . ?
O2 C3 1.3393(12) . ?
C1 C2 1.4459(14) . ?
C2 C3 1.3993(13) . ?
C2 C11 1.4454(13) . ?
C3 C4 1.4251(14) . ?
C4 C5 1.3670(14) . ?
C4 C12 1.5081(13) . ?
C5 C6 1.4212(14) . ?
C6 C7 1.4144(14) . ?
C6 C11 1.4199(14) . ?
C7 C8 1.3726(14) . ?
C8 C9 1.3946(14) . ?
C9 C10 1.3669(14) . ?
C10 C11 1.4154(13) . ?
C12 C13 1.5249(13) . ?
C13 C14 1.5228(13) . ?
C14 C15 1.5219(16) . ?
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
O2 H2 O1 0.84 1.80 2.5457(9) 147.6 .
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
F1 C9 C10 C11 -179.70(7) . . . . ?
O1 C1 C2 C3 -1.14(15) . . . . ?
O1 C1 C2 C11 -179.63(9) . . . . ?
O2 C3 C4 C5 -178.74(8) . . . . ?
O2 C3 C4 C12 0.89(13) . . . . ?
C1 C2 C3 O2 1.19(14) . . . . ?
C1 C2 C3 C4 -178.42(8) . . . . ?
C1 C2 C11 C6 177.29(8) . . . . ?
C1 C2 C11 C10 -2.12(14) . . . . ?
C2 C3 C4 C5 0.89(14) . . . . ?
C2 C3 C4 C12 -179.49(8) . . . . ?
C3 C2 C11 C6 -1.18(13) . . . . ?
C3 C2 C11 C10 179.41(8) . . . . ?
C3 C4 C5 C6 -0.81(14) . . . . ?
C3 C4 C12 C13 -178.80(8) . . . . ?
C4 C5 C6 C7 179.86(8) . . . . ?
C4 C5 C6 C11 -0.27(14) . . . . ?
C4 C12 C13 C14 180.00(8) . . . . ?
C5 C4 C12 C13 0.80(14) . . . . ?
C5 C6 C7 C8 179.72(8) . . . . ?
C5 C6 C11 C2 1.27(13) . . . . ?
C5 C6 C11 C10 -179.29(8) . . . . ?
C6 C7 C8 C9 -0.19(14) . . . . ?
C7 C6 C11 C2 -178.86(8) . . . . ?
C7 C6 C11 C10 0.58(13) . . . . ?
C7 C8 C9 F1 -179.86(8) . . . . ?
C7 C8 C9 C10 0.08(15) . . . . ?
C8 C9 C10 C11 0.36(15) . . . . ?
C9 C10 C11 C2 178.73(8) . . . . ?
C9 C10 C11 C6 -0.68(13) . . . . ?
C11 C2 C3 O2 179.71(8) . . . . ?
C11 C2 C3 C4 0.11(14) . . . . ?
C11 C6 C7 C8 -0.14(14) . . . . ?
C12 C4 C5 C6 179.59(8) . . . . ?
C12 C13 C14 C15 -173.71(9) . . . . ?
