Copper-catalyzed intramolecular cross dehydrogenative coupling approach to coumestans from 2′-hydroxyl-3-arylcoumarins
Song, Xianheng; Luo, Xiang; Sheng, Jianfei; Li, Jianheng; Zhu, Zefeng; Du, Zhibo; Miao, Hui; Yan, Meng; Li, Mingkang; Zou, Yong; RSC Advances 9 (2019) 17391–; doi:10.1039/C9RA01909J

data_7232862
_publ_section_title
;
 Copper-catalyzed intramolecular cross dehydrogenative coupling approach
 to coumestans from 2&#x2032;-hydroxyl-3-arylcoumarins
;
_journal_issue                   30
_journal_name_full               'RSC Advances'
_journal_page_first              17391
_journal_paper_doi               10.1039/C9RA01909J
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C18 H14 O6'
_chemical_formula_sum            'C18 H14 O6'
_chemical_formula_weight         326.31
_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
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-05-25 deposited with the CCDC.    2019-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                78.547(5)
_cell_angle_beta                 77.009(5)
_cell_angle_gamma                73.528(6)
_cell_formula_units_Z            4
_cell_length_a                   9.1056(6)
_cell_length_b                   11.7060(8)
_cell_length_c                   14.8314(8)
_cell_measurement_reflns_used    4930
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.9820
_cell_measurement_theta_min      4.0240
_cell_volume                     1461.74(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9971
_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     33.00 104.00   1.00    3.00    --   44.40  57.00  30.00   71
  2  \w     96.00 174.00   1.00   10.00    --  100.00 125.00  30.00   78
  3  \w     75.00 114.00   1.00    3.00    --   44.40 125.00-180.00   39
  4  \w     74.00 173.00   1.00   10.00    --  100.00 125.00-120.00   99
  5  \w     86.00 118.00   1.00   10.00    --  100.00 -45.00-120.00   32
  6  \w     48.00 114.00   1.00   10.00    --  100.00 -30.00 -30.00   66
  7  \w     63.00 121.00   1.00   10.00    --  100.00-125.00 120.00   58
  8  \w     91.00 123.00   1.00   10.00    --  100.00 -61.00 120.00   32
  9  \w     31.00  56.00   1.00   10.00    --  100.00-125.00  30.00   25
 10  \w     27.00 120.00   1.00   10.00    --  100.00-125.00   0.00   93
 11  \w     43.00 101.00   1.00   10.00    --  100.00 -94.00-180.00   58
 12  \w     17.00  77.00   1.00   10.00    --  100.00 -94.00  30.00   60
 13  \w     22.00 139.00   1.00   10.00    --  100.00 -15.00  90.00  117
 14  \w    -66.00  25.00   1.00    3.00    --  -44.40  57.00 -30.00   91
 15  \w    -69.00  19.00   1.00    3.00    --  -44.40  57.00-150.00   88
 16  \w    -89.00 -40.00   1.00   10.00    --  -90.00  61.00-150.00   49
 17  \w   -129.00 -86.00   1.00   10.00    --  -90.00  15.00 -90.00   43
 18  \w   -125.00 -88.00   1.00    3.00    --  -44.40 -99.00 120.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0981891000
_diffrn_orient_matrix_UB_12      0.1312628000
_diffrn_orient_matrix_UB_13      -0.0106332000
_diffrn_orient_matrix_UB_21      -0.1466552000
_diffrn_orient_matrix_UB_22      -0.0422310000
_diffrn_orient_matrix_UB_23      0.0511684000
_diffrn_orient_matrix_UB_31      0.0318110000
_diffrn_orient_matrix_UB_32      0.0148720000
_diffrn_orient_matrix_UB_33      0.0942009000
_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  0.0611
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11521
_diffrn_reflns_theta_full        67.0771
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         3.09
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.944
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.4826
_exptl_crystal_description       block
_exptl_crystal_F_000             682.5671
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.4364
_refine_diff_density_min         -0.4025
_refine_diff_density_rms         0.0936
_refine_ls_d_res_high            0.8370
_refine_ls_d_res_low             14.3006
_refine_ls_goodness_of_fit_ref   1.0177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    44
_refine_ls_number_parameters     439
_refine_ls_number_reflns         5184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0177
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0641
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1489P)^2^+0.4372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1851
_refine_ls_wR_factor_ref         0.2124
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                4161
_reflns_number_total             5184
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9ra01909j4.cif
_cod_data_source_block           sjf_170512_2
_cod_database_code               7232862
_reflns_odcompleteness_completeness 99.71
_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.a Aromatic/amide H refined with riding coordinates:
 C34(H34), C40(H40), C38(H38), C46(H46), C41(H41), C37(H37), C26(H26),
 C0aa(H0aa), C42(H42), C35(H35)
2.b Idealised Me refined as rotating group:
 C32(H32a,H32b,H32c), C36(H36a,H36b,H36c), C43(H43a,H43b,H43c), C44(H44a,H44b,
 H44c), C45(H45a,H45b,H45c), C47(H47a,H47b,H47c)
;
_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 2.521
_oxdiff_exptl_absorpt_empirical_full_min 0.329