Crystal Structure of [3-(1,4,7,10-Tetraazacyclododecan-1-yl)propan-1-amine]zinc(II) Bis(perchlorate), [Zn<sup>II</sup>L](ClO<sub>4</sub>)<sub>2</sub>
ICHIMARU, Yoshimi; IMAI, Masanori; FUJIOKA, Haruto; HIEDA, Yuhzo; KOIKE, Tohru; KUROSAKI, Hiromasa; KATO, Koichi; X-ray Structure Analysis Online 36 (2020) 43–44; doi:10.2116/xraystruct.36.43

data_1559468
_publ_section_title
;
 Crystal Structure of
 [3-(1,4,7,10-Tetraazacyclododecan-1-yl)propan-1-amine]zinc(II)
 Bis(perchlorate),
 [Zn&lt;sup&gt;II&lt;/sup&gt;L](ClO&lt;sub&gt;4&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;
;
_journal_issue                   0
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              43
_journal_page_last               44
_journal_paper_doi               10.2116/xraystruct.36.43
_journal_volume                  36
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H27 N5 Zn, 2(Cl O4)'
_chemical_formula_sum            'C11 H27 Cl2 N5 O8 Zn'
_chemical_formula_weight         493.64
_chemical_name_systematic
'[3-(1,4,7,10-tetraazacyclododecam-1-yl)propan-1-amine]zinc(II)'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-29
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.09970(10)
_cell_length_b                   14.0995(2)
_cell_length_c                   14.9908(2)
_cell_measurement_reflns_used    3079
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      68.07
_cell_measurement_theta_min      4.305
_cell_volume                     1923.34(4)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_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    -31.00  -6.00   0.50    0.20    --  -41.33  34.00   5.00   50
  2  \w    -56.00 -29.00   0.50    0.20    --  -95.73  50.00 -30.00   54
  3  \w   -105.00 -72.00   0.50    0.20    --  -41.33 168.00   5.00   66
  4  \w    -69.00 -44.00   0.50    0.20    --  -95.73  59.00  90.00   50
  5  \w    -46.00 -21.00   0.50    0.20    --  -41.33  90.00 139.00   50
  6  \w   -100.00 -19.00   0.50    0.20    --  -41.33 138.00 120.00  162
  7  \w     46.00 100.00   0.50    0.20    --   42.58 168.00   5.00  108
  8  \w     64.00 101.00   0.50    0.20    --   42.58 138.00   0.00   74
  9  \w     72.00  98.00   0.50    0.20    --   96.98 168.00   5.00   52
 10  \w     51.00  89.00   0.50    0.20    --   42.58  34.00   5.00   76
 11  \w    100.00 126.00   0.50    0.20    --   96.98  34.00   5.00   52
 12  \w     49.00 106.00   0.50    0.20    --   96.98 -90.00  24.00  114
 13  \w     30.00  56.00   0.50    0.20    --   96.98 -50.00 -30.00   52
 14  \w     30.00  66.00   0.50    0.20    --   96.98 -59.00 -60.00   72
 15  \w    -14.00  11.00   0.50    0.20    --   42.58 -34.00-152.00   50
 16  \w     29.00  68.00   0.50    0.20    --   96.98 -59.00-150.00   78
 17  \w     45.00  83.00   0.50    0.20    --   96.98 -68.00-180.00   76
 18  \w    -24.00   2.00   0.50    0.20    --   42.58 -11.00 -90.00   52
 19  \w    -64.00 -39.00   0.50    0.20    --  -41.33 114.00-138.00   50
 20  \w     13.00  42.00   0.50    0.20    --   42.58 -90.00  24.00   58
 21  \w     29.00  62.00   0.50    0.20    --   96.98 -59.00  90.00   66
 22  \w     45.00  71.00   0.50    0.20    --   96.98-114.00 131.00   52
 23  \w     31.00  57.00   0.50    0.20    --   96.98 -50.00 150.00   52
 24  \w    123.00 148.00   0.50    0.20    --   96.98  90.00 139.00   50
 25  \w    -69.00 -44.00   0.50    0.20    --  -95.73  68.00-120.00   50
 26  \w    -95.00 -67.00   0.50    0.20    --  -95.73 114.00-138.00   56
 27  \w    -92.00 -67.00   0.50    0.20    --  -41.33 -34.00-152.00   50
 28  \w   -145.00 -82.00   0.50    0.20    --  -95.73 -34.00-152.00  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0210798000
_diffrn_orient_matrix_UB_12      -0.1074881000
_diffrn_orient_matrix_UB_13      0.0131318000
_diffrn_orient_matrix_UB_21      -0.0714899000
_diffrn_orient_matrix_UB_22      0.0069893000
_diffrn_orient_matrix_UB_23      0.0929292000
_diffrn_orient_matrix_UB_31      -0.1520077000
_diffrn_orient_matrix_UB_32      -0.0181997000
_diffrn_orient_matrix_UB_33      -0.0419174000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuKa
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6590
_diffrn_reflns_point_group_measured_fraction_full 0.884
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.072
_diffrn_reflns_theta_min         4.305
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffration, 2020)'
_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    1.705
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_preparation
'H. Fujioka, et al., J. Sep. Sci. 2014, 37, 1601-1609'
_exptl_crystal_size_max          0.471
_exptl_crystal_size_mid          0.301
_exptl_crystal_size_min          0.276
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1056 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.025(9)
_refine_ls_extinction_coef       0.00260(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0214
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0317P)^2^+0.1512P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0535
_refine_ls_wR_factor_ref         0.0538
_reflns_Friedel_coverage         0.546
_reflns_Friedel_fraction_full    0.733
_reflns_Friedel_fraction_max     0.729
_reflns_number_gt                3044
_reflns_number_total             3079
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            36_43_1.txt
_cod_data_source_block           exp_19
_cod_database_code               1559468
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H23 N5 O8 Cl2 Zn1'
_shelx_estimated_absorpt_t_max   0.351
_shelx_estimated_absorpt_t_min   0.211
_diffrn_oxdiff_digest_frames
;
0128a45a47cb5925d25bb4ceddb4460af301898895d
;
_diffrn_oxdiff_digest_hkl
;
014db6bb96fa03b8fea31023798ba87e4a26d9
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2), N3(H3), N4(H4)
2.b Secondary CH2 refined with riding coordinates:
 N5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C5(H5C,H5D), C11(H11A,H11B), C4(H4A,
 H4B), C3(H3A,H3B), C8(H8A,H8B), C2(H2A,H2B), C9(H9A,H9B), C1(H1A,H1B),
 C10(H10A,H10B)
;
_shelx_res_checksum              15318
_shelx_hkl_checksum              4157
_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 1.353
_oxdiff_exptl_absorpt_empirical_full_min 0.720