Oxidative [4 + 2] annulation of 1-naphthols with alkynes accelerated by an electron-deficient rhodium(III) catalysts.
Araujo Dias, Antônio Junio; Takahashi, Hiroto; Nogami, Juntaro; Nagashima, Yuki; Tanaka, Ken; Organic & biomolecular chemistry 20 (2022) 1008–1012; doi:10.1039/d1ob02181h

data_7158455
_publ_section_title
;
 Oxidative [4 + 2] annulation of 1-naphthols with alkynes accelerated by
 an electron-deficient rhodium(III) catalysts.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1008
_journal_page_last               1012
_journal_paper_doi               10.1039/d1ob02181h
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C27 H22 O4'
_chemical_formula_sum            'C27 H22 O4'
_chemical_formula_weight         410.47
_chemical_melting_point          452.0(10)
_chemical_name_systematic
6-Methoxy-2,3-bis(4-methoxyphenyl)benzo[de]chromene
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-04
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2021-09-08 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                82.076(4)
_cell_angle_beta                 78.416(4)
_cell_angle_gamma                65.109(4)
_cell_formula_units_Z            2
_cell_length_a                   9.6823(4)
_cell_length_b                   10.4434(4)
_cell_length_c                   11.6367(5)
_cell_measurement_reflns_used    6202
_cell_measurement_temperature    210
_cell_measurement_theta_max      30.3390
_cell_measurement_theta_min      2.2160
_cell_volume                     1043.73(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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_temperature      210
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.933
_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     74.00 103.00   0.50   11.41    --   20.00  54.00  93.14   58
  2  \w    -65.00  23.00   0.50   11.41    --   20.00  54.00 -60.00  176
  3  \w     72.00 107.00   0.50   11.41    --   20.00  54.00 -60.00   70
  4  \w    -73.00 -23.00   0.50   11.41    --   20.00  54.00-180.00  100
  5  \w     66.00 101.00   0.50   11.41    --   20.00  54.00-180.00   70
  6  \w    -72.00  62.00   0.50   11.41    --   20.00  54.00  30.00  268
  7  \w    -71.00  -7.00   0.50   11.41    --   20.00  54.00 120.00  128
  8  \w     16.00  42.00   0.50   11.41    --   20.00  54.00 120.00   52
  9  \w    -73.00 -26.00   0.50   11.41    --   20.00  54.00-120.00   94
 10  \w    -71.00  69.00   0.50   11.41    --   20.00  54.00   0.00  280
 11  \w    -24.00  28.00   0.50   11.41    --   20.00  54.00 150.00  104
 12  \w     83.00 108.00   0.50   11.41    --   20.00  54.00 150.00   50
 13  \w    -69.00  60.00   0.50   11.41    --   20.00  54.00 -90.00  258
 14  \w    -69.00   4.00   0.50   11.41    --   20.00  54.00  93.14  146
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II (JP)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0614135000
_diffrn_orient_matrix_UB_12      -0.0052419000
_diffrn_orient_matrix_UB_13      -0.0467180000
_diffrn_orient_matrix_UB_21      0.0446151000
_diffrn_orient_matrix_UB_22      0.0025680000
_diffrn_orient_matrix_UB_23      0.0403986000
_diffrn_orient_matrix_UB_31      0.0304780000
_diffrn_orient_matrix_UB_32      -0.0747814000
_diffrn_orient_matrix_UB_33      0.0084151000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16753
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.469
_diffrn_reflns_theta_min         2.154
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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    1.297
_exptl_crystal_description       block
_exptl_crystal_F_000             430
_exptl_crystal_recrystallization_method 'From the Melt'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         5933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0464
_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/[\s^2^(Fo^2^)+(0.0754P)^2^+0.1325P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1404
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4621
_reflns_number_total             5933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02181h2.cif
_cod_data_source_block           exp_392
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '451-453' was changed to
'452.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158455.cif.

2025-04-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C56 H46 O6'
_cod_original_formula_weight         814.93
_cod_original_formula_moiety         '2(C27 H22 O4)'
_cod_original_formula_units_Z            1
_cod_database_code               7158455
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C56 H46 O6 '
_chemical_oxdiff_usercomment     220K
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.968
_diffrn_oxdiff_digest_frames
;
016dae52a6b42d0e81d47e053083f6087f0002588c7
;
_diffrn_oxdiff_digest_hkl
;
01c1d119e49fda450e27a61d92f342c196b2b5
;
_reflns_odcompleteness_completeness 99.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00R(H00R),
 C00S(H00S)
2.b Idealised Me refined as rotating group:
 C00T(H00A,H00B,H00D), C00U(H00I,H00K,H00Q), C00V(H00T,H00U,H00V)
;
_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 1.118
_oxdiff_exptl_absorpt_empirical_full_min 0.943