Straightforward synthesis of bis-tetraazacycloalkanes: towards new potential CXCR4 antagonists?
Sok, Nicolas; Baglin, Isabelle; Basset, Christelle; Fakkor, Fatima; Kohli, Evelyne; Rousselin, Yoann; Bernhard, Claire; Boschetti, Frédéric; Goze, Christine; Denat, Franck; RSC Adv. 7 (2017) 28291–; doi:10.1039/C7RA04218C

data_7228346
_publ_section_title
;
 Straightforward synthesis of bis-tetraazacycloalkanes: towards new
 potential CXCR4 antagonists?
;
_journal_issue                   45
_journal_name_full               'RSC Adv.'
_journal_page_first              28291
_journal_paper_doi               10.1039/C7RA04218C
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C27 H51 N11, H2 O'
_chemical_formula_sum            'C27 H53 N11 O'
_chemical_formula_weight         547.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-01
_audit_creation_method
;
Olex2 1.2
(compiled Feb 16 2016 13:09:46 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-04-26 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 123.022(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4773(5)
_cell_length_b                   14.9989(4)
_cell_length_c                   21.0082(7)
_cell_measurement_reflns_used    6421
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     3032.3(2)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR97 (Burla et al., 2007)'
_diffrn_ambient_temperature      115(2)
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       '\f and \w scans''
_diffrn_orient_matrix_type       'Nonius Collect from scalepack cell'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10062
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.783
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_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    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method
'The material was recrystallised from ether by slow evaporation'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.988
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5308
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0828
_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^)+(0.0659P)^2^+7.6741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1885
_refine_ls_wR_factor_ref         0.2062
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4136
_reflns_number_total             5308
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {9af17915-6190-4092-a302-a37855ef3ff5}
_cod_data_source_file            c7ra04218c2.cif
_cod_data_source_block           compound_5
_cod_original_cell_volume        3032.29(19)
_cod_database_code               7228346
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Riding coordinates:
 N1(H1), N2(H2), N3(H3), N5(H5), N7(H7A), N9(H9), N10(H10), N11(H11A)
3.b Free rotating group:
 O1(H1C,H1D)
3.c Ternary CH refined with riding coordinates:
 C7(H7), C11(H11), C17(H17), C19(H19)
3.d Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C18(H18A,H18B), C20(H20A,H20B),
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B),
  C26(H26A,H26B), C27(H27A,H27B)
3.e Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15)
;
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a glass fibre oil'
_olex2_submission_special_instructions 'No special instructions were received'