Electron-rich benzofulvenes as effective dipolarophiles in copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides.
Chang, Xin; Liu, Xue-Tao; Li, Fangfang; Yang, Yuhong; Chung, Lung Wa; Wang, Chun-Jiang; Chemical science 14 (2023) 5460–5469; doi:10.1039/d3sc00435j

data_1568955
_publ_section_title
;
 Electron-rich benzofulvenes as effective dipolarophiles in
 copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine
 ylides.
;
_journal_issue                   20
_journal_name_full               'Chemical science'
_journal_page_first              5460
_journal_page_last               5469
_journal_paper_doi               10.1039/d3sc00435j
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H25 N O2'
_chemical_formula_sum            'C26 H25 N O2'
_chemical_formula_weight         383.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-01-07 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.79993(4)
_cell_length_b                   15.89690(8)
_cell_length_c                   18.74294(10)
_cell_measurement_reflns_used    34084
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6000
_cell_measurement_theta_min      3.6390
_cell_volume                     2026.071(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_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    -28.00  31.00   0.50    0.50    --    0.00 -82.00   0.00  118
  2  \w     14.00  61.00   0.50    0.50    --   32.00 -78.00  61.74   94
  3  \w    -39.00  10.00   0.50    0.50    --   32.00 -78.00  61.74   98
  4  \w     17.00  57.00   0.50    0.50    --   44.00  71.00  29.81   80
  5  \w     90.00 131.00   0.50    0.50    --   44.00  71.00  29.81   82
  6  \w     91.00 117.00   0.50    0.50    --   48.00  72.00  90.13   52
  7  \w     88.00 134.00   0.50    0.50    --   48.00  72.00-105.06   92
  8  \w     21.00  46.00   0.50    0.50    --   48.00  72.00  90.13   50
  9  \w     21.00  54.00   0.50    0.50    --   48.00  72.00-105.06   66
 10  \w     30.00  65.00   0.50    0.50    --   56.00  71.00 -79.13   70
 11  \w     29.00  78.00   0.50    0.50    --   56.00  71.00 164.95   98
 12  \w    119.00 145.00   0.50    0.50    --   56.00  71.00 -79.13   52
 13  \w    101.00 126.00   0.50    0.50    --   56.00  75.00 110.95   50
 14  \w     32.00  57.00   0.50    0.50    --   56.00  75.00 110.95   50
 15  \w     33.00  86.00   0.50    0.50    --   60.00  73.00-178.61  106
 16  \w     99.00 149.00   0.50    0.50    --   60.00  75.00  -9.95  100
 17  \w     33.00  59.00   0.50    0.50    --   60.00  75.00  -9.95   52
 18  \w     40.00  66.00   0.50    0.50    --   68.00  75.00  -1.84   52
 19  \w     40.00  65.00   0.50    0.50    --   68.00  75.00  45.97   50
 20  \w     41.00  66.00   0.50    0.50    --   68.00  73.00 -35.67   50
 21  \w     44.00  82.00   0.50    0.50    --   72.00  74.00  84.39   76
 22  \w     44.00  70.00   0.50    0.50    --   72.00  74.00 -75.64   52
 23  \w     44.00  94.00   0.50    0.50    --   72.00  75.00-110.02  100
 24  \w     44.00  73.00   0.50    0.50    --   72.00  75.00-150.28   58
 25  \w     44.00  69.00   0.50    0.50    --   72.00  74.00  56.23   50
 26  \w     45.00  74.00   0.50    0.50    --   72.00  71.00 132.75   58
 27  \w     57.00  83.00   0.50    0.50    --   80.00  62.00 -46.44   52
 28  \w    134.00 173.00   0.50    0.50    --   84.00  68.00   9.99   78
 29  \w     59.00 127.00   0.50    0.50    --   84.00  68.00   9.99  136
 30  \w     60.00 170.00   0.50    0.50    --   88.00  75.00-129.12  220
 31  \w     64.00 174.00   0.50    0.50    --   88.00  63.00 159.71  220
 32  \w     71.00 150.00   0.50    0.50    --   94.60  63.00 -15.38  158
 33  \w      6.00 121.00   0.50    0.50    --   94.60 -82.00 -90.00  230
 34  \w     52.00  81.00   0.50    0.50    --   94.60 -77.00  90.00   58
 35  \w     87.00 177.00   0.50    0.50    --   94.60  82.00  90.00  180
 36  \w     59.00 112.00   0.50    0.50    --   94.60 -61.00 150.00  106
 37  \w      9.00  54.00   0.50    0.50    --   94.60 -61.00 150.00   90
 38  \w     75.00 151.00   0.50    0.50    --   94.60  45.00 -60.00  152
 39  \w     68.00  98.00   0.50    0.50    --   94.60 -61.00 -30.00   60
 40  \w     71.00 104.00   0.50    0.50    --   94.60  61.00 -30.00   66
 41  \w     67.00 144.00   0.50    0.50    --   94.60  72.00  29.84  154
 42  \w     71.00 105.00   0.50    0.50    --   94.60  61.00-150.00   68
 43  \w      8.00 115.00   0.50    0.50    --   94.60 -61.00 -90.00  214
 44  \w    123.00 183.00   0.50    0.50    --   94.60  61.00 -30.00  120
 45  \w     62.00 100.00   0.50    0.50    --   94.60 -82.00 150.00   76
 46  \w     79.00 144.00   0.50    0.50    --   94.60  61.00  60.00  130
 47  \w      7.00  59.00   0.50    0.50    --   94.60 -82.00 150.00  104
 48  \w     70.00 117.00   0.50    0.50    --   94.60  65.00 -49.68   94
 49  \w    139.00 184.00   0.50    0.50    --   94.60  82.00-150.00   90
 50  \w     64.00 118.00   0.50    0.50    --   94.60 -82.00  30.00  108
 51  \w     87.00 136.00   0.50    0.50    --   94.60  82.00-150.00   98
 52  \w     68.00 180.00   0.50    0.50    --   94.60  73.00 110.57  224
 53  \w     71.00  96.00   0.50    0.50    --   94.60  61.00  90.00   50
 54  \w     69.00 183.00   0.50    0.50    --   94.60  66.00 169.27  228
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0189634000
_diffrn_orient_matrix_UB_12      0.0898756000
_diffrn_orient_matrix_UB_13      0.0300323000
_diffrn_orient_matrix_UB_21      0.0242167000
_diffrn_orient_matrix_UB_22      0.0361499000
_diffrn_orient_matrix_UB_23      -0.0757439000
_diffrn_orient_matrix_UB_31      -0.2244086000
_diffrn_orient_matrix_UB_32      -0.0037042000
_diffrn_orient_matrix_UB_33      -0.0107206000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            45070
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.862
_diffrn_reflns_theta_min         3.646
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1663 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(6)
_refine_ls_extinction_coef       0.0039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0306
_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/[\s^2^(Fo^2^)+(0.0461P)^2^+0.3903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                3968
_reflns_number_total             4050
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00435j2.cif
_cod_data_source_block           20210507_lxt-1-139
_cod_depositor_comments
'Adding full bibliography for 1568955--1568956.cif.'
_cod_original_cell_volume        2026.072(19)
_cod_database_code               1568955
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.747
_reflns_odcompleteness_completeness 99.81
_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 Ternary CH refined with riding coordinates:
 C00N(H00P), C007(H007)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00F(H00F), C00G(H00G), C00I(H00K), C00M(H00O),
 C00P(H00Q), C00Q(H00R), C00R(H00S), C00S(H00T), C00T(H00U), C006(H006),
 C008(H008)
2.c Idealised Me refined as rotating group:
 C00E(H00B,H00D,H00E), C00H(H00H,H00I,H00J), C00L(H00L,H00M,H00N)
;
_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 2.456
_oxdiff_exptl_absorpt_empirical_full_min 0.454