Synthesis of chiral nine and twelve-membered cyclic polyamines from natural building blocks
Müntener, Thomas; Thommen, Fabienne; Joss, Daniel; Kottelat, Jérémy; Prescimone, Alessandro; Häussinger, Daniel; Chemical Communications  (2019) –; doi:10.1039/C9CC00720B

data_7123219
_publ_section_title
;
 Synthesis of chiral nine and twelve-membered cyclic polyamines from
 natural building blocks
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC00720B
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_compound_source        'Thomas Muentener'
_chemical_formula_moiety         'C16 H36 N4'
_chemical_formula_sum            'C16 H36 N4'
_chemical_formula_weight         284.49
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2018-04-20
_audit_creation_method           CRYSTALS_ver_14.61_build_6720
_audit_update_record
;
2018-12-21 deposited with the CCDC.    2019-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.271(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5648(11)
_cell_length_b                   19.708(2)
_cell_length_c                   9.8034(11)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    123
_cell_measurement_theta_max      70
_cell_measurement_theta_min      4
_cell_volume                     1782.7(3)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10762
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         69.961
_diffrn_reflns_theta_min         4.487
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.060
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method ' '
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.12
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 1285 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.08(10)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8694
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3070
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0261
_refine_ls_shift/su_max          0.0002863
_refine_ls_shift/su_mean         0.0000263
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 2.97 4.43 2.03 0.497 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0589
_refine_ls_wR_factor_gt          0.0588
_refine_ls_wR_factor_ref         0.0589
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              23
_reflns_limit_k_min              -21
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                3041
_reflns_number_total             3083
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0264
_oxford_refine_ls_scale          0.13377(4)
_oxford_reflns_number_all        3070
_oxford_structure_analysis_title 'FT057_123K_0m in C2'
_cod_data_source_file            c9cc00720b2.cif
_cod_data_source_block           FT057_123K
_cod_original_cell_volume        1782.7(4)
_cod_original_sg_symbol_H-M      'C 2 '
_cod_database_code               7123219
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_hooft_y                  0.06(10)
_oxford_bijvoet_difference       0.08(10)
_oxford_refined_flack_x          0.0(3)