#------------------------------------------------------------------------------
#$Date: 2020-07-07 03:59:40 +0300 (Tue, 07 Jul 2020) $
#$Revision: 254040 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/85/1558508.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_1558508
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 H16 O2'
_chemical_formula_sum            'C15 H16 O2'
_chemical_formula_weight         228.28
_chemical_name_systematic        3-Butyl-2-hydroxy-1-naphthaldehyde
_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
_audit_creation_date             2015-12-03
_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                 99.928(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3890(5)
_cell_length_b                   12.5456(4)
_cell_length_c                   7.5297(3)
_cell_measurement_reflns_used    1886
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.5170
_cell_measurement_theta_min      4.2470
_cell_volume                     1152.80(8)
_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      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -90.00  -57.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.3887 -178.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega  -18.00    9.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574  -57.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -42.00   83.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8574   19.0000   60.0000 125
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0238325000
_diffrn_orient_matrix_UB_12      0.0462614000
_diffrn_orient_matrix_UB_13      0.0311769000
_diffrn_orient_matrix_UB_21      0.0515934000
_diffrn_orient_matrix_UB_22      0.0145084000
_diffrn_orient_matrix_UB_23      0.0506389000
_diffrn_orient_matrix_UB_31      0.0121657000
_diffrn_orient_matrix_UB_32      0.0290670000
_diffrn_orient_matrix_UB_33      -0.0749190000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4219
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         3.191
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49398
_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_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane and hexane'
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0434
_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)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1124
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1680
_reflns_number_total             2233
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02502j2.cif
_cod_data_source_block           an1molt
_cod_original_cell_volume        1152.81(8)
_cod_database_code               1558508
_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 99.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C15(H15)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-12-03
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.02198(8) 0.36952(8) 0.17380(14) 0.0204(3) Uani 1 1 d . . . . .
H1 H -0.0323 0.3362 0.1986 0.031 Uiso 1 1 calc GR . . . .
O2 O -0.09269(8) 0.21205(9) 0.23505(14) 0.0248(3) Uani 1 1 d . . . . .
C1 C 0.10044(11) 0.30005(12) 0.15002(17) 0.0156(3) Uani 1 1 d . . . . .
C2 C 0.08425(11) 0.19016(12) 0.16052(18) 0.0153(3) Uani 1 1 d . . . . .
C3 C 0.16957(11) 0.11849(12) 0.12885(18) 0.0154(3) Uani 1 1 d . . . . .
C4 C 0.15944(12) 0.00600(12) 0.12649(18) 0.0181(3) Uani 1 1 d . . . . .
H4 H 0.0927 -0.0257 0.1452 0.022 Uiso 1 1 calc R . . . .
C5 C 0.24442(12) -0.05771(12) 0.09768(18) 0.0204(4) Uani 1 1 d . . . . .
H5 H 0.2361 -0.1330 0.0979 0.025 Uiso 1 1 calc R . . . .
C6 C 0.34336(12) -0.01326(13) 0.06795(18) 0.0206(4) Uani 1 1 d . . . . .
H6 H 0.4022 -0.0582 0.0496 0.025 Uiso 1 1 calc R . . . .
C7 C 0.35488(12) 0.09470(13) 0.06542(18) 0.0197(4) Uani 1 1 d . . . . .
H7 H 0.4217 0.1245 0.0429 0.024 Uiso 1 1 calc R . . . .
C8 C 0.26951(11) 0.16293(12) 0.09557(17) 0.0156(3) Uani 1 1 d . . . . .
C9 C 0.28132(11) 0.27579(11) 0.09077(18) 0.0159(3) Uani 1 1 d . . . . .
H9 H 0.3488 0.3042 0.0685 0.019 Uiso 1 1 calc R . . . .
C10 C 0.20090(11) 0.34491(12) 0.11643(18) 0.0154(3) Uani 1 1 d . . . . .
C11 C 0.21063(11) 0.46445(12) 0.11141(19) 0.0174(3) Uani 1 1 d . . . . .
H11A H 0.1980 0.4931 0.2286 0.021 Uiso 1 1 calc R . . . .
H11B H 0.1514 0.4920 0.0174 0.021 Uiso 1 1 calc R . . . .
C12 C 0.31871(12) 0.50769(12) 0.07457(18) 0.0165(3) Uani 1 1 d . . . . .
H12A H 0.3322 0.4801 -0.0428 0.020 Uiso 1 1 calc R . . . .
H12B H 0.3786 0.4820 0.1692 0.020 Uiso 1 1 calc R . . . .
C13 C 0.32008(12) 0.62911(12) 0.0708(2) 0.0206(4) Uani 1 1 d . . . . .
H13A H 0.2576 0.6547 -0.0192 0.025 Uiso 1 1 calc R . . . .
H13B H 0.3103 0.6565 0.1903 0.025 Uiso 1 1 calc R . . . .
C14 C 0.42584(12) 0.67377(13) 0.0245(2) 0.0250(4) Uani 1 1 d . . . . .
H14A H 0.4347 0.6490 -0.0956 0.038 Uiso 1 1 calc GR . . . .
H14B H 0.4880 0.6493 0.1138 0.038 Uiso 1 1 calc GR . . . .
H14C H 0.4230 0.7518 0.0253 0.038 Uiso 1 1 calc GR . . . .
C15 C -0.01634(12) 0.15318(13) 0.21166(19) 0.0197(4) Uani 1 1 d . . . . .
H15 H -0.0244 0.0787 0.2285 0.024 Uiso 1 1 calc R . . . .
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'
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 121.30(12) . . ?
O1 C1 C10 116.21(13) . . ?
C2 C1 C10 122.48(13) . . ?
C1 C2 C3 119.37(12) . . ?
C1 C2 C15 118.12(13) . . ?
C3 C2 C15 122.44(13) . . ?
C4 C3 C2 123.96(12) . . ?
C4 C3 C8 117.86(13) . . ?
C8 C3 C2 118.17(13) . . ?
C5 C4 C3 120.98(13) . . ?
C4 C5 C6 120.78(14) . . ?
C7 C6 C5 119.68(14) . . ?
C6 C7 C8 121.22(14) . . ?
C3 C8 C9 119.45(13) . . ?
C7 C8 C3 119.45(14) . . ?
C7 C8 C9 121.10(13) . . ?
C10 C9 C8 123.32(13) . . ?
C1 C10 C11 118.24(12) . . ?
C9 C10 C1 117.15(13) . . ?
C9 C10 C11 124.61(13) . . ?
C10 C11 C12 116.02(12) . . ?
C11 C12 C13 112.00(12) . . ?
C14 C13 C12 112.68(12) . . ?
O2 C15 C2 124.27(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
O1 C1 1.3405(16) . ?
O2 C15 1.2365(17) . ?
C1 C2 1.397(2) . ?
C1 C10 1.4277(19) . ?
C2 C3 1.4387(19) . ?
C2 C15 1.4429(18) . ?
C3 C4 1.417(2) . ?
C3 C8 1.4190(19) . ?
C4 C5 1.369(2) . ?
C5 C6 1.399(2) . ?
C6 C7 1.362(2) . ?
C7 C8 1.409(2) . ?
C8 C9 1.424(2) . ?
C9 C10 1.3596(19) . ?
C10 C11 1.5055(19) . ?
C11 C12 1.5140(19) . ?
C12 C13 1.5238(19) . ?
C13 C14 1.5199(19) . ?
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
O1 H1 O2 0.84 1.77 2.5218(14) 148.1 .
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
O1 C1 C2 C3 178.19(11) . . . . ?
O1 C1 C2 C15 -4.7(2) . . . . ?
O1 C1 C10 C9 -179.58(11) . . . . ?
O1 C1 C10 C11 0.29(18) . . . . ?
C1 C2 C3 C4 -176.44(13) . . . . ?
C1 C2 C3 C8 2.70(19) . . . . ?
C1 C2 C15 O2 5.1(2) . . . . ?
C1 C10 C11 C12 -179.77(12) . . . . ?
C2 C1 C10 C9 1.3(2) . . . . ?
C2 C1 C10 C11 -178.80(13) . . . . ?
C2 C3 C4 C5 -179.19(12) . . . . ?
C2 C3 C8 C7 179.53(12) . . . . ?
C2 C3 C8 C9 -1.32(19) . . . . ?
C3 C2 C15 O2 -177.88(13) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C3 C8 C9 C10 -0.1(2) . . . . ?
C4 C3 C8 C7 -1.28(19) . . . . ?
C4 C3 C8 C9 177.87(13) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C5 C6 C7 C8 1.2(2) . . . . ?
C6 C7 C8 C3 -0.1(2) . . . . ?
C6 C7 C8 C9 -179.26(13) . . . . ?
C7 C8 C9 C10 179.04(13) . . . . ?
C8 C3 C4 C5 1.7(2) . . . . ?
C8 C9 C10 C1 0.1(2) . . . . ?
C8 C9 C10 C11 -179.72(13) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C10 C1 C2 C3 -2.8(2) . . . . ?
C10 C1 C2 C15 174.30(12) . . . . ?
C10 C11 C12 C13 179.58(12) . . . . ?
C11 C12 C13 C14 -177.05(12) . . . . ?
C15 C2 C3 C4 6.6(2) . . . . ?
C15 C2 C3 C8 -174.24(12) . . . . ?
