Synthesis of Multisubstituted 1-Naphthoic Acids via Ru-Catalyzed C-H Activation and Double-Alkyne Annulation under Air.
Chen, Honghao; Ouyang, Lufeng; Liu, Jidan; Shi, Wen-Jing; Chen, Guoshu; Zheng, Liyao; The Journal of organic chemistry 84 (2019) 12755–12763; doi:10.1021/acs.joc.9b00926

data_4034077
_publ_section_title
;
 Synthesis of Multisubstituted 1-Naphthoic Acids via Ru-Catalyzed C-H
 Activation and Double-Alkyne Annulation under Air.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12755
_journal_page_last               12763
_journal_paper_doi               10.1021/acs.joc.9b00926
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C36 H26 O3'
_chemical_formula_sum            'C36 H26 O3'
_chemical_formula_weight         506.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                111.0730(10)
_cell_angle_beta                 116.2030(10)
_cell_angle_gamma                91.8030(10)
_cell_formula_units_Z            2
_cell_length_a                   11.38000(10)
_cell_length_b                   11.38120(10)
_cell_length_c                   12.3023(2)
_cell_measurement_reflns_used    11393
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      76.6330
_cell_measurement_theta_min      4.2730
_cell_volume                     1299.13(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9880
_diffrn_measured_fraction_theta_max 0.9880
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -24.00   3.00   0.50    0.05    --   46.37 -57.00 -90.00   54
  2  \w     28.00  63.00   0.50    0.05    --   46.37 -57.00 -90.00   70
  3  \w     13.00  63.00   0.50    0.05    --   46.37-113.00-144.00  100
  4  \w     35.00  66.00   0.50    0.10    --  107.00 -94.00-150.00   62
  5  \w     71.00 102.00   0.50    0.10    --  107.00 -94.00-150.00   62
  6  \w     54.00 109.00   0.50    0.10    --  107.00-113.00-144.00  110
  7  \w     37.00  68.00   0.50    0.10    --  107.00 -30.00-150.00   62
  8  \w     92.00 117.00   0.50    0.05    --   46.37  57.00-150.00   50
  9  \w     85.00 145.00   0.50    0.10    --  107.00 113.00 -52.00  120
 10  \w    108.00 143.00   0.50    0.10    --  107.00  61.00-150.00   70
 11  \w     84.00 130.00   0.50    0.10    --  107.00 -77.00  60.00   92
 12  \w     67.00 102.00   0.50    0.10    --  107.00 -94.00 120.00   70
 13  \w     35.00  81.00   0.50    0.10    --  107.00 -77.00  60.00   92
 14  \w     39.00 107.00   0.50    0.10    --  107.00 -94.00  60.00  136
 15  \w     32.00  64.00   0.50    0.10    --  107.00 -30.00 -30.00   64
 16  \w     31.00 106.00   0.50    0.10    --  107.00 -15.00 -30.00  150
 17  \w     37.00 107.00   0.50    0.05    --   46.37  37.00 120.00  140
 18  \w     34.00  62.00   0.50    0.10    --  107.00 -30.00  90.00   56
 19  \w     33.00  67.00   0.50    0.10    --  107.00 -30.00  60.00   68
 20  \w    -78.00  -4.00   0.50    0.05    --  -46.37 113.00 -52.00  148
 21  \w    -61.00  25.00   0.50    0.05    --  -46.37  37.00 -90.00  172
 22  \w    -57.00 -29.00   0.50    0.10    -- -102.00  45.00 -30.00   56
 23  \w    -67.00 -29.00   0.50    0.10    -- -102.00  30.00   0.00   76
 24  \w    -70.00 -32.00   0.50    0.10    -- -102.00  45.00 -60.00   76
 25  \w    -73.00 -32.00   0.50    0.10    -- -102.00  45.00 -90.00   82
 26  \w    -76.00 -50.00   0.50    0.10    -- -102.00 113.00 -52.00   52
 27  \w    -59.00 -32.00   0.50    0.10    -- -102.00 125.00   0.00   54
 28  \w    -97.00 -65.00   0.50    0.10    -- -102.00 125.00   0.00   64
 29  \w   -107.00 -79.00   0.50    0.10    -- -102.00 113.00 -52.00   56
 30  \w   -104.00 -32.00   0.50    0.10    -- -102.00  77.00 -30.00  144
 31  \w    -61.00 -30.00   0.50    0.10    -- -102.00  30.00  30.00   62
 32  \w    -57.00 -32.00   0.50    0.10    -- -102.00 125.00 120.00   50
 33  \w   -117.00 -91.00   0.50    0.10    -- -102.00 125.00 120.00   52
 34  \w   -117.00 -36.00   0.50    0.10    -- -102.00 125.00 -30.00  162
 35  \w   -157.00 -87.00   0.50    0.10    -- -102.00 -15.00  90.00  140
 36  \w   -118.00 -71.00   0.50    0.05    --  -46.37-125.00   0.00   94
 37  \w   -114.00 -71.00   0.50    0.05    --  -46.37-125.00-120.00   86
 38  \w   -142.00 -81.00   0.50    0.10    -- -102.00-113.00-144.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0143080000
_diffrn_orient_matrix_UB_12      0.0217327000
_diffrn_orient_matrix_UB_13      -0.1214453000
_diffrn_orient_matrix_UB_21      0.0092161000
_diffrn_orient_matrix_UB_22      0.1447937000
_diffrn_orient_matrix_UB_23      0.0727611000
_diffrn_orient_matrix_UB_31      0.1539935000
_diffrn_orient_matrix_UB_32      0.0274062000
_diffrn_orient_matrix_UB_33      0.0593557000
_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  0.0204
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14617
_diffrn_reflns_theta_full        69.9941
_diffrn_reflns_theta_max         69.99
_diffrn_reflns_theta_min         4.27
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_colour_primary    'pale yellow'
_exptl_crystal_density_diffrn    1.2950
_exptl_crystal_description       needle
_exptl_crystal_F_000             533.6341
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.2396
_refine_diff_density_min         -0.1932
_refine_diff_density_rms         0.0411
_refine_ls_d_res_high            0.8204
_refine_ls_d_res_low             10.3423
_refine_ls_goodness_of_fit_ref   1.0654
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     357
_refine_ls_number_reflns         4861
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0653
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+0.4944P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1003
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                4505
_reflns_number_total             4861
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b00926_si_002.cif
_cod_data_source_block           zly-OMe
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4034077
_chemical_oxdiff_formula         'C H O'
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O36-H36
 0.85 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27),
  C28(H28), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34)
3.b Idealised Me refined as rotating group:
 C39(H39a,H39b,H39c)
;
_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 1.393
_oxdiff_exptl_absorpt_empirical_full_min 0.606