C-Functionalized chiral dioxocyclam and cyclam derivatives with 1,2,3-triazole units: synthesis, complexation properties and crystal structures of copper(ii) complexes
Felten, A.-S.; Petry, N.; Henry, B.; Pellegrini-Moïse, N.; Selmeczi, K.; New J. Chem. 40 (2016) 1507–; doi:10.1039/C5NJ01927C

data_7055188
_publ_section_title
;
 C-Functionalized chiral dioxocyclam and cyclam derivatives with
 1,2,3-triazole units: synthesis, complexation properties and crystal
 structures of copper(ii) complexes
;
_journal_issue                   2
_journal_name_full               'New J. Chem.'
_journal_page_first              1507
_journal_paper_doi               10.1039/C5NJ01927C
_journal_volume                  40
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H30 Cu N10 O2, 2(H2 O)'
_chemical_formula_sum            'C23 H34 Cu N10 O4'
_chemical_formula_weight         578.14
_chemical_name_common            '[Cu(syn-25)]'
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-10-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_audit_update_record
;
2015-11-05 deposited with the CCDC.
2015-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.25040(10)
_cell_length_b                   12.25040(10)
_cell_length_c                   42.3729(7)
_cell_measurement_reflns_used    21229
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1430
_cell_measurement_theta_min      3.7090
_cell_volume                     6359.00(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    SIR2012
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.4508
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  Atlas
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0796
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            89613
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         76.835
_diffrn_reflns_theta_min         3.756
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.322
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       plate
_exptl_crystal_F_000             2424
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: H2O/MeCN/MeOH'
_exptl_crystal_size_max          0.1591
_exptl_crystal_size_mid          0.1423
_exptl_crystal_size_min          0.0455
_platon_squeeze_details
;
TITL katalin-nip037-38-3 in P 41 21 2
CELL   12.2504   12.2504   42.3729     90.00     90.00     90.00
SPGR P43212
C101 0.669 0.388 0.484 !      11.89 eA-3
C102 0.472 0.325 0.259 !       8.81 eA-3
C103 0.277 0.415 0.024 !       7.42 eA-3
C104 0.013 0.821-0.002 !       7.06 eA-3
C105 0.732 0.766 0.484 !       6.43 eA-3
C106 0.268 1.002 0.725 !       6.29 eA-3
C107 0.953 0.830 0.494 !       6.24 eA-3
C108 0.547 0.542 0.009 !       5.48 eA-3
C109 0.329 0.383 0.260 !       3.98 eA-3
C110 0.704 0.332 0.249 !       1.70 eA-3
Q111 0.941 0.279 0.438 !       1.29 eA-3
C112 0.335 0.742 0.508 !       1.21 eA-3
Q113 0.343 0.735 0.901 !       1.14 eA-3
Q114 0.468 0.828 0.203 !       1.04 eA-3
Q115 0.393 0.287 0.172 !       0.99 eA-3
Q116 0.064 0.230 0.086 !       0.99 eA-3
Q117 0.059 0.208 0.930 !       0.99 eA-3
C118 0.732 0.150 0.239 !       0.92 eA-3
Q119 0.560 0.148 0.165 !       0.92 eA-3
Q120 0.782 0.449 0.424 !       0.90 eA-3
Q121 0.969 0.413 0.720 !       0.89 eA-3
Q122 0.064 0.274 0.743 !       0.88 eA-3
Q123 0.029 0.509 0.555 !       0.88 eA-3
Q124 0.982 0.298 0.735 !       0.85 eA-3
C125 0.533 0.294 0.991 !       0.83 eA-3
Q126 0.051 0.522 0.477 !       0.82 eA-3
C127 0.828 0.312 0.499 !       0.82 eA-3
Q128 0.374 0.926 0.649 !       0.81 eA-3
Q129 0.201 0.180 0.079 !       0.81 eA-3
Q130 0.610 0.806 0.575 !       0.79 eA-3
Q131 0.794 0.638 0.414 !       0.79 eA-3
C132 0.938 0.849 0.299 !       0.78 eA-3
Q133 0.534 0.737 0.580 !       0.78 eA-3
Q134 0.125 0.716 0.665 !       0.77 eA-3
C135 0.216 0.660 0.757 !       0.77 eA-3
Q136 0.738 0.508 0.702 !       0.75 eA-3
Q137 0.668 0.245 0.335 !       0.73 eA-3
Q138 0.247 0.319 0.094 !       0.73 eA-3
Q139 0.187 0.188 0.330 !       0.73 eA-3
C140 0.077 0.078-0.001 !       0.71 eA-3
Q141 0.923 0.387 0.179 !       0.71 eA-3
Q142 0.047 0.013 0.923 !       0.71 eA-3
C143 0.667 0.622 0.233 !       0.71 eA-3
Q144 0.253 0.764 0.835 !       0.71 eA-3
Q145 0.103 0.494 0.805 !       0.68 eA-3
Q146 0.189 0.558 0.030 !       0.67 eA-3
Q147 1.000 0.669 0.412 !       0.65 eA-3
Q148 0.655 0.365 0.991 !       0.64 eA-3
Q149 0.203 0.159 0.389 !       0.64 eA-3
Q150 0.346 0.532 0.971 !       0.64 eA-3
C151 0.715 0.942 0.249 !       0.63 eA-3
C152 0.158 0.014 0.768 !       0.62 eA-3
Q153 0.516 0.901 0.204 !       0.61 eA-3
C154 0.825 0.045 0.254 !       0.61 eA-3
Q155 0.788 0.919 0.842 !       0.60 eA-3
C156 0.415 0.600 0.969 !       0.60 eA-3
Q157 0.891 0.260-0.002 !       0.60 eA-3
Q158 0.705 0.431 0.874 !       0.59 eA-3
Q159 0.513 0.678 0.662 !       0.59 eA-3
Q160 0.764 0.740 0.576 !       0.58 eA-3
Q161 0.296 0.802 0.899 !       0.58 eA-3
Q162 0.765 0.298 0.594 !       0.57 eA-3
Q163 0.814 0.091 0.150 !       0.57 eA-3
Q164 0.300 0.759 0.178 !       0.57 eA-3
Q165 0.254 0.579 0.734 !       0.57 eA-3
C166 0.831 0.913 0.017 !       0.56 eA-3
Q167 0.112 0.333 0.562 !       0.55 eA-3
Q168 1.003 0.864 0.577 !       0.55 eA-3
Q169 0.262 0.886 0.664 !       0.55 eA-3
Q170 0.033 0.620 0.322 !       0.54 eA-3
Q171 0.048 0.856 0.665 !       0.54 eA-3
C172 0.989 0.796 0.516 !       0.54 eA-3
C173 0.092 0.682 0.767 !       0.54 eA-3
C174 0.078 0.868 0.773 !       0.54 eA-3
Q175 0.388 0.252 0.765 !       0.54 eA-3
C176 0.718 0.788 0.515 !       0.54 eA-3
C177 0.879 0.901 0.485 !       0.53 eA-3
Q178 0.998 0.109 0.916 !       0.52 eA-3
Q179 0.766 0.084 0.490 !       0.51 eA-3
Q180 0.781 0.823 0.351 !       0.51 eA-3
Q181 0.204 0.285 0.374 !       0.51 eA-3
Q182 0.127 0.595 0.492 !       0.51 eA-3
C183 0.033 0.977 0.287 !       0.50 eA-3
The electron count of SQUEEZE and void shapes agree with
four water molecules per asymmetric unit. Totaly there are six water
molecules with 2 water molecules modelled per asymmetric unit.
;
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 2467 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6691
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0516P)^2^+5.4498P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                6396
_reflns_number_total             6691
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5nj01927c2.cif
_cod_data_source_block           platon_sq
_cod_depositor_comments
'Adding full bibliography for 7055187--7055188.cif.'
_cod_original_cell_volume        6359.00(15)
_cod_database_code               7055188
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H,H) groups
2. Restrained distances
 N4-H4 = N11-H11
 0.96 with sigma of 0.02
 H2WA-H2WB
 1.56 with sigma of 0.01
 H1WA-H1WB
 1.56 with sigma of 0.02
 O2W-H2WA = O2W-H2WB
 1 with sigma of 0.01
 O1W-H1WA = O1W-H1WB
 1 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C2(H2), C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C6A(H6AA,H6AB), C6B(H6BA,H6BB),
 C7A(H7AA,H7AB), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C4B(H4B), C5A(H5AA), C5B(H5BA), C9A(H9A), C10A(H10C), C11A(H11A), C12A(H12C),
 C13A(H13C)
;
_shelx_fab_checksum              58983
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_platon_squeeze_void_probe_radius 1.20