Annulative Morita-Baylis-Hillman reaction to synthesise chiral dibenzocycloheptanes.
Mondal, Atanu; Shivangi, ?; Tung, Pinku; Wagulde, Siddhant V.; Ramasastry, S. S. V.; Chemical communications (Cambridge, England) 57 (2021) 9260–9263; doi:10.1039/d1cc02765d

data_7128812
_publ_section_title
;
 Annulative Morita-Baylis-Hillman reaction to synthesise chiral
 dibenzocycloheptanes.
;
_journal_issue                   73
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9260
_journal_page_last               9263
_journal_paper_doi               10.1039/d1cc02765d
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C29 H26 O2'
_chemical_formula_sum            'C29 H26 O2'
_chemical_formula_weight         406.50
_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             2021-04-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-27 deposited with the CCDC.	2021-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                87.619(5)
_cell_angle_beta                 87.821(4)
_cell_angle_gamma                72.126(5)
_cell_formula_units_Z            2
_cell_length_a                   9.1696(5)
_cell_length_b                   10.6774(7)
_cell_length_c                   12.2477(7)
_cell_measurement_reflns_used    4735
_cell_measurement_temperature    298.0(2)
_cell_measurement_theta_max      29.0860
_cell_measurement_theta_min      2.9730
_cell_volume                     1139.88(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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_temperature      298.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.939
_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    -69.00 118.20   0.30    7.00    --   29.89  54.00-180.00  624
  2  \w    -69.00 118.20   0.30    7.00    --   29.89  54.00   0.00  624
  3  \w    -69.00 118.20   0.30    7.00    --   29.89  54.00   0.00  624
  4  \w    -69.00 118.20   0.30    7.00    --   29.89  54.00 -60.00  624
  5  \w    -69.00  62.10   0.30    7.00    --   29.89  54.00  90.00  437
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0646270000
_diffrn_orient_matrix_UB_12      -0.0226469000
_diffrn_orient_matrix_UB_13      0.0337721000
_diffrn_orient_matrix_UB_21      -0.0254268000
_diffrn_orient_matrix_UB_22      -0.0535607000
_diffrn_orient_matrix_UB_23      0.0191774000
_diffrn_orient_matrix_UB_31      0.0422777000
_diffrn_orient_matrix_UB_32      -0.0386664000
_diffrn_orient_matrix_UB_33      -0.0430553000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25197
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.765
_diffrn_reflns_theta_min         2.566
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         7910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0799
_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^)+(0.1574P)^2^+0.0512P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2234
_refine_ls_wR_factor_ref         0.2854
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4487
_reflns_number_total             7910
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02765d2.cif
_cod_data_source_block           am0605
_cod_depositor_comments
'Adding full bibliography for 7128811--7128812.cif.'
_cod_database_code               7128812
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C29O2H25
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.971
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C25(H25), C21(H21), C18(H18), C26(H26), C28(H28), C9(H9), C27(H27),
 C24(H24), C22(H22), C5(H5), C8(H8), C23(H23), C6(H6)
2.d Idealised Me refined as rotating group:
 C2(H2a,H2b,H2c), C29(H29a,H29b,H29c), C10(H10a,H10b,H10c)
;
_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 1.352
_oxdiff_exptl_absorpt_empirical_full_min 0.796