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_7123220
_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         'C12 H30 Cl1 N4 O1.50'
_chemical_formula_sum            'C12 H30 Cl N4 O1.5'
_chemical_formula_weight         289.85
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2018-01-18
_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                 106.439(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0294(5)
_cell_length_b                   14.6457(9)
_cell_length_c                   12.7180(7)
_cell_measurement_reflns_used    8065
_cell_measurement_temperature    123
_cell_measurement_theta_max      70
_cell_measurement_theta_min      5
_cell_volume                     1613.10(16)
_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 0.986
_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     1.54180
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11474
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         70.065
_diffrn_reflns_theta_min         3.623
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.104
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             636
_exptl_crystal_recrystallization_method
; 
CD2Cl2
;
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.14
_refine_diff_density_min         -0.30
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 2041 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.074(11)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8964
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5188
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.0001910
_refine_ls_shift/su_mean         0.0000232
_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: 
 8.25 12.5 5.76 1.34 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1315
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1315
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              17
_reflns_limit_k_min              -16
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                4746
_reflns_number_total             5212
_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   0.0546
_oxford_refine_ls_scale          0.18363(15)
_oxford_reflns_number_all        5188
_oxford_structure_analysis_title 'TM11301_A_0m in P2(1)'
_cod_data_source_file            c9cc00720b2.cif
_cod_data_source_block           TM11301_A
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        'C12 H30 Cl1 N4 O1.50'
_cod_database_code               7123220
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_hooft_y                  0.081(10)
_oxford_bijvoet_difference       0.074(11)
_oxford_refined_flack_x          0.039(16)