Crystal Structure of [1<sup>1</sup>,1<sup>4</sup>,1<sup>7</sup>,1<sup>10</sup>,5<sup>1</sup>,5<sup>4</sup>,5<sup>7</sup>,5<sup>10</sup>-Octaaza-1,5(1,4)-dicyclododecana-3,7(1,3)-dibenzenacyclooctaphane]zinc(II) tetrakis(nitrate), [<i>m,m</i>-bis(Zn<sup>II</sup>-cyclen)](NO<sub>3</sub>)<sub>4</sub>
ICHIMARU, Yoshimi; JIN, Wanchun; YAMAGUCHI, Yoshihiro; SUGIURA, Kirara; IMAI, Masanori; KUROSAKI, Hiromasa; FUJIOKA, Haruto; KOIKE, Tohru; HIEDA, Yuhzo; KATO, Koichi; X-ray Structure Analysis Online 37 (2021) 15–16; doi:10.2116/xraystruct.37.15

data_1561477
_publ_section_title
;
 Crystal Structure of
 [1&lt;sup&gt;1&lt;/sup&gt;,1&lt;sup&gt;4&lt;/sup&gt;,1&lt;sup&gt;7&lt;/sup&gt;,1&lt;sup&gt;10&lt;/sup&gt;,5&lt;sup&gt;1&lt;/sup&gt;,5&lt;sup&gt;4&lt;/sup&gt;,5&lt;sup&gt;7&lt;/sup&gt;,5&lt;sup&gt;10&lt;/sup&gt;-Octaaza-1,5(1,4)-dicyclododecana-3,7(1,3)-dibenzenacyclooctaphane]zinc(II)
 tetrakis(nitrate),
 [&lt;i&gt;m,m&lt;/i&gt;-bis(Zn&lt;sup&gt;II&lt;/sup&gt;-cyclen)](NO&lt;sub&gt;3&lt;/sub&gt;)&lt;sub&gt;4&lt;/sub&gt;
;
_journal_issue                   0
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              15
_journal_page_last               16
_journal_paper_doi               10.2116/xraystruct.37.15
_journal_volume                  37
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H52 N10 O6 Zn2, 4(H2 O), 2(N O3)'
_chemical_formula_sum            'C32 H60 N12 O16 Zn2'
_chemical_formula_weight         999.66
_chemical_name_systematic
'[1,1,1,1,5,5,5,5-octaaza-1,5(1,4)-dicyclododecana-3,7(1,3)-dibenzenacyclooctaphane]zinc(II)'
_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_Hall           'P 31 2"'
_space_group_name_H-M_alt        'P 31 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-02
_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                120
_cell_formula_units_Z            3
_cell_length_a                   8.97880(10)
_cell_length_b                   8.97880(10)
_cell_length_c                   44.4258(6)
_cell_measurement_reflns_used    7754
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      68.1170
_cell_measurement_theta_min      2.9820
_cell_volume                     3101.72(6)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_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                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_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    -42.00 -12.00   0.50    0.20    --  -41.21  65.00  60.00   60
  2  \w     -9.00  27.00   0.50    0.20    --  -41.21  65.00  60.00   72
  3  \w    -20.00  32.00   0.50    0.20    --  -41.21  11.00 120.00  104
  4  \w     41.00  68.00   0.50    0.20    --   42.46  49.00 136.00   54
  5  \w     72.00 103.00   0.50    0.20    --   42.46  49.00 136.00   62
  6  \w     83.00 164.00   0.50    0.20    --   96.98  27.00 122.00  162
  7  \w     71.00  99.00   0.50    0.20    --   42.46 138.00 150.00   56
  8  \w     12.00  46.00   0.50    0.20    --   42.46 -43.00  60.00   68
  9  \w     30.00  56.00   0.50    0.20    --   96.98 -50.00 120.00   52
 10  \w    -28.00  -3.00   0.50    0.20    --   42.46 -11.00 120.00   50
 11  \w   -102.00 -76.00   0.50    0.20    --  -41.21-147.00  57.00   52
 12  \w   -157.00 -89.00   0.50    0.20    --  -95.73 -59.00   0.00  136
 13  \w    -78.00 -52.00   0.50    0.20    --  -95.73  68.00 -60.00   52
 14  \w    -55.00 -29.00   0.50    0.20    --  -95.73  50.00-150.00   52
 15  \w   -136.00 -85.00   0.50    0.20    --  -95.73 -37.00-149.00  102
 16  \w   -158.00-110.00   0.50    0.20    --  -95.73 -19.00-116.00   96
 17  \w    -30.00  16.00   0.50    0.20    --   42.46 -11.00-150.00   92
 18  \w     37.00  77.00   0.50    0.20    --   96.98 -68.00-180.00   80
 19  \w     32.00 105.00   0.50    0.20    --   96.98-124.00-137.00  146
 20  \w     30.00  55.00   0.50    0.20    --   96.98 -50.00 -30.00   50
 21  \w    -71.00 -27.00   0.50    0.20    --  -95.73  77.00 150.00   88
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0555550000
_diffrn_orient_matrix_UB_12      0.0291542000
_diffrn_orient_matrix_UB_13      -0.0332913000
_diffrn_orient_matrix_UB_21      0.1060957000
_diffrn_orient_matrix_UB_22      -0.0894739000
_diffrn_orient_matrix_UB_23      0.0051707000
_diffrn_orient_matrix_UB_31      -0.1579116000
_diffrn_orient_matrix_UB_32      -0.1743265000
_diffrn_orient_matrix_UB_33      -0.0082354000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            9471
_diffrn_reflns_point_group_measured_fraction_full 0.879
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.203
_diffrn_reflns_theta_min         2.984
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.74a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.606
_exptl_crystal_description       block
_exptl_crystal_F_000             1572
_exptl_crystal_preparation       'See preparation reference'
_exptl_crystal_recrystallization_method 'Recrystallized by water'
_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.566
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1021 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.030(11)
_refine_ls_extinction_coef       0.00071(8)
_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   1.158
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0272P)^2^+1.9751P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0621
_refine_ls_wR_factor_ref         0.0623
_reflns_Friedel_coverage         0.469
_reflns_Friedel_fraction_full    0.704
_reflns_Friedel_fraction_max     0.698
_reflns_number_gt                3300
_reflns_number_total             3323
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            37_15_1.txt
_cod_data_source_block           exp_14zncyclenmxylyl
_cod_original_cell_volume        3101.72(8)
_cod_database_code               1561477
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_digest_frames
;
01a7a529a6255f20b1942bcf120ada85c30168668d7
;
_diffrn_oxdiff_digest_hkl
;
01eb4be82621f17de848def523d76da8139df8
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 O9-H9C = O9-H9D
 0.85 with sigma of 0.02
 O8-H8C = O8-H8D
 0.85 with sigma of 0.02
 H9C-H9D
 1.34 with sigma of 0.04
 H8C-H8D
 1.34 with sigma of 0.04
3.a Ternary CH refined with riding coordinates:
 N3(H3), N2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C3(H3A,H3B), C16(H16A,H16B), C7(H7A,H7B), C1(H1A,H1B), C8(H8A,
 H8B), C4(H4A,H4B), C6(H6A,H6B), C2(H2A,H2B), C5(H5A,H5B)
3.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C13(H13), C11(H11), C12(H12)
;
_shelx_res_checksum              99728
_shelx_hkl_checksum              43161
_olex2_exptl_crystal_mounting_method
'Crystal mounting utilized MiTiGen Dual-Thichness MicroLoops LD'
_olex2_submission_original_sample_id 'Zn m-xylyl-cyclen'
_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 2.024
_oxdiff_exptl_absorpt_empirical_full_min 0.673