Unexpected Diels-Alder reaction of [60]fullerene with electron-deficient ferrocenes as cyclopentadiene surrogates
Wang, Guan-Wu; Liu, Zhan; Yin, Zheng-Chun; Lu, Wen-Qiang; Zhou, Dian-Bing; Chemical Communications  (2021) –; doi:10.1039/D1CC05749A

data_7129226
_publ_section_title
;
 Unexpected Diels-Alder reaction of [60]fullerene with electron-deficient
 ferrocenes as cyclopentadiene surrogates
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05749A
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H15 N O3'
_chemical_formula_sum            'C17 H15 N O3'
_chemical_formula_weight         281.30
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-03-05
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2021-07-14 deposited with the CCDC.	2021-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.91306(11)
_cell_length_b                   10.84345(15)
_cell_length_c                   14.26741(17)
_cell_measurement_reflns_used    3915
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9970
_cell_measurement_theta_min      4.0850
_cell_volume                     1378.92(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 97-2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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   -110.00 -13.00   1.00    2.00    --  -40.80 -57.00  90.00   97
  2  \w    -65.00  15.00   1.00    2.00    --  -40.80  38.00 -30.00   80
  3  \w     25.00 139.00   1.00    4.00    --   99.68 -15.00-180.00  114
  4  \w     35.00 109.00   1.00    4.00    --   99.68 -94.00 -90.00   74
  5  \w     17.00  91.00   1.00    4.00    --   99.68 -94.00   0.00   74
  6  \w    127.00 153.00   1.00    4.00    --   99.68 125.00  60.00   26
  7  \w     44.00  93.00   1.00    4.00    --   99.68 -30.00 -60.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0157928000
_diffrn_orient_matrix_UB_12      -0.0932930000
_diffrn_orient_matrix_UB_13      -0.0808404000
_diffrn_orient_matrix_UB_21      0.0321077000
_diffrn_orient_matrix_UB_22      -0.1033638000
_diffrn_orient_matrix_UB_23      0.0713101000
_diffrn_orient_matrix_UB_31      -0.1690971000
_diffrn_orient_matrix_UB_32      -0.0283391000
_diffrn_orient_matrix_UB_33      0.0059720000
_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  0.0189
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4471
_diffrn_reflns_theta_full        70.11
_diffrn_reflns_theta_max         70.11
_diffrn_reflns_theta_min         5.12
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.092(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0588P)^2^+0.1078P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0878
_reflns_number_gt                2482
_reflns_number_total             2529
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1cc05749a2.cif
_cod_data_source_block           lz20210305-1
_cod_database_code               7129226
_chemical_oxdiff_formula         C17H15N1O3
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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
2.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C13(H13), C17(H17), C14(H14), C16(H16), C15(H15)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 1.442
_oxdiff_exptl_absorpt_empirical_full_min 0.512