Reversible C‒C bond formation: solid state structure of the aldol-like addition product of adamantanone to a 1,5-diazapentadienyllithium, and its solution state retro-aldol dissociation
Ball, Lee-Jon; Dickie, Anthony P.; Mair, Francis S.; Middleton, David A.; Pritchard, Robin G.; Chemical Communications (Cambridge, United Kingdom)  (2003) 744–745; doi:10.1039/b211745b

data_7104013
_publ_section_title
;
 Reversible C--C bond formation: solid state structure of the aldol-like
 addition product of adamantanone to a 1,5-diazapentadienyllithium, and
 its solution state retro-aldol dissociation
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   6
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              744
_journal_page_last               745
_journal_paper_doi               10.1039/b211745b
_journal_year                    2003
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C66 H86 Li2 N4 O2'
_chemical_formula_sum            'C66 H86 Li2 N4 O2'
_chemical_formula_weight         981.27
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2002-10-09T00:05:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6269(3)
_cell_length_b                   22.2662(3)
_cell_length_c                   23.8287(4)
_cell_measurement_reflns_used    40910
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     5638.36(13)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.365857E-1
_diffrn_orient_matrix_UB_12      0.222348E-1
_diffrn_orient_matrix_UB_13      0.326078E-1
_diffrn_orient_matrix_UB_21      -0.776783E-1
_diffrn_orient_matrix_UB_22      -0.84144E-2
_diffrn_orient_matrix_UB_23      0.22344E-1
_diffrn_orient_matrix_UB_31      0.385036E-1
_diffrn_orient_matrix_UB_32      -0.381028E-1
_diffrn_orient_matrix_UB_33      0.140938E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            37520
_diffrn_reflns_reduction_process
;
Scaled and merged with SORTAV
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.75
_diffrn_reflns_theta_max         25.75
_diffrn_reflns_theta_min         3.76
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_correction_T_min  0.9899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.17
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1011
_refine_ls_number_reflns         10524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0214P)^2^+1.2608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0848
_reflns_number_gt                8360
_reflns_number_total             10524
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7113750
_cod_data_source_file            b211745b.txt
_cod_data_source_block           u
_cod_database_code               7104013