#------------------------------------------------------------------------------
#$Date: 2020-08-06 16:06:02 +0300 (Thu, 06 Aug 2020) $
#$Revision: 254915 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/66/7126635.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7126635
loop_
_publ_author_name
'Shircliff, Anthony D.'
'Burke, Benjamin P.'
'Davilla, Dustin J.'
'Burgess, Gwendolyn E.'
'Okorocha, Faith A.'
'Shrestha, Alina'
'Allbritton, Elisabeth M. A.'
'Nguyen, Phillip T.'
'Lamar, Rachael L.'
'Jones, Donald G.'
'Gorbet, Michael-Joseph'
'Allen, Michael B.'
'Eze, John I.'
'Fernandez, Andrea T.'
'Ramirez, Daniel'
'Archibald, Stephen J.'
'Prior, Timothy J.'
'Krause, Jeanette A.'
'Oliver, Allen G.'
'Hubin, Timothy J.'
_publ_section_title
;
 An ethylene cross-bridged pentaazamacrocycle and its Cu²⁺
 complex: constrained ligand topology and excellent kinetic stability.
;
_journal_issue                   54
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7519
_journal_page_last               7522
_journal_paper_doi               10.1039/d0cc00919a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C15 H33 Cu N5, 0.45(Cl O4), 1.55(Cl)'
_chemical_formula_sum            'C15 H33 Cl2 Cu N5 O1.79'
_chemical_formula_weight         446.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-02-03 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.357(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8067(14)
_cell_length_b                   15.792(2)
_cell_length_c                   14.030(2)
_cell_measurement_reflns_used    2803
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.1205
_cell_measurement_theta_min      2.8125
_cell_volume                     1951.2(5)
_computing_cell_refinement       'Bruker SAINT v8.37A'
_computing_data_collection       'Bruker APEX3 v2016.1.0'
_computing_data_reduction        'Bruker SAINT v8.37A'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.24
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'omega-phi scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7749
_diffrn_reflns_av_R_equivalents  0.1643
_diffrn_reflns_av_unetI/netI     0.1545
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20954
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        27.706
_diffrn_reflns_theta_max         29.076
_diffrn_reflns_theta_min         2.117
_diffrn_source                   'ALS beamline 11.3.1.'
_exptl_absorpt_coefficient_mu    1.783
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.7057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_description       plate
_exptl_crystal_F_000             941
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.002
_refine_diff_density_max         1.111
_refine_diff_density_min         -0.875
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4026
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1734
_refine_ls_R_factor_gt           0.0787
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0939P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1748
_refine_ls_wR_factor_ref         0.2109
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2053
_reflns_number_total             4026
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc00919a2.cif
_cod_data_source_block           gb08a
_cod_depositor_comments
'Adding full bibliography for 7126634--7126636.cif.'
_cod_original_cell_volume        1951.1(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7126635
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.932
_shelx_estimated_absorpt_t_max   0.996
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.74078(10) 0.25258(6) 0.91504(6) 0.0261(3) Uani 1 1 d . . . . .
N1 N 0.5986(7) 0.3290(4) 0.8421(4) 0.0295(15) Uani 1 1 d . . . . .
N2 N 0.5750(7) 0.1633(4) 0.9045(4) 0.0282(15) Uani 1 1 d . . . . .
N3 N 0.8942(7) 0.1565(4) 0.9229(4) 0.0306(15) Uani 1 1 d . . . . .
N4 N 0.9118(7) 0.3263(4) 0.8630(4) 0.0321(16) Uani 1 1 d . . . . .
N5 N 0.7259(7) 0.3478(4) 1.0254(4) 0.0285(15) Uani 1 1 d . . . . .
C1 C 0.5043(10) 0.2698(5) 0.7846(6) 0.041(2) Uani 1 1 d . . . . .
H1A H 0.564871 0.247310 0.731034 0.050 Uiso 1 1 calc R U . . .
H1B H 0.415957 0.300509 0.757535 0.050 Uiso 1 1 calc R U . . .
C2 C 0.4503(9) 0.1985(5) 0.8448(5) 0.039(2) Uani 1 1 d . . . . .
H2A H 0.367604 0.218740 0.886491 0.047 Uiso 1 1 calc R U . . .
H2B H 0.408601 0.153322 0.803303 0.047 Uiso 1 1 calc R U . . .
C3 C 0.5123(10) 0.1305(5) 0.9945(6) 0.044(2) Uani 1 1 d . . . . .
H3A H 0.437872 0.085982 0.980480 0.065 Uiso 1 1 calc R U . . .
H3B H 0.462706 0.176645 1.029095 0.065 Uiso 1 1 calc R U . . .
H3C H 0.594624 0.107043 1.033705 0.065 Uiso 1 1 calc R U . . .
C4 C 0.6604(10) 0.0967(5) 0.8518(6) 0.038(2) Uani 1 1 d . . . . .
H4A H 0.681742 0.116599 0.786323 0.046 Uiso 1 1 calc R U . . .
H4B H 0.598138 0.044677 0.847264 0.046 Uiso 1 1 calc R U . . .
C5 C 0.8076(10) 0.0773(5) 0.9027(6) 0.045(2) Uani 1 1 d . . . . .
H5A H 0.785973 0.047757 0.963315 0.053 Uiso 1 1 calc R U . . .
H5B H 0.869837 0.039224 0.862745 0.053 Uiso 1 1 calc R U . . .
C6 C 0.9853(9) 0.1453(5) 1.0117(5) 0.040(2) Uani 1 1 d . . . . .
H6A H 1.056167 0.098064 1.003612 0.060 Uiso 1 1 calc R U . . .
H6B H 0.917307 0.133292 1.065050 0.060 Uiso 1 1 calc R U . . .
H6C H 1.042487 0.197307 1.024978 0.060 Uiso 1 1 calc R U . . .
C7 C 0.9956(9) 0.1801(5) 0.8430(5) 0.035(2) Uani 1 1 d . . . . .
H7A H 0.941135 0.172357 0.781635 0.042 Uiso 1 1 calc R U . . .
H7B H 1.085701 0.142582 0.843024 0.042 Uiso 1 1 calc R U . . .
C8 C 1.0452(9) 0.2703(5) 0.8527(6) 0.040(2) Uani 1 1 d . . . . .
H8A H 1.112303 0.276237 0.909140 0.048 Uiso 1 1 calc R U . . .
H8B H 1.103587 0.287140 0.795630 0.048 Uiso 1 1 calc R U . . .
C9 C 0.8501(9) 0.3528(5) 0.7681(5) 0.038(2) Uani 1 1 d . . . . .
H9A H 0.848203 0.303574 0.724375 0.046 Uiso 1 1 calc R U . . .
H9B H 0.916247 0.396778 0.740144 0.046 Uiso 1 1 calc R U . . .
C10 C 0.6902(9) 0.3874(5) 0.7798(6) 0.042(2) Uani 1 1 d . . . . .
H10A H 0.694741 0.444431 0.809110 0.050 Uiso 1 1 calc R U . . .
H10B H 0.640602 0.392717 0.716581 0.050 Uiso 1 1 calc R U . . .
C11 C 0.9399(10) 0.3987(5) 0.9279(6) 0.042(2) Uani 1 1 d . . . . .
H11A H 0.888382 0.449651 0.902336 0.050 Uiso 1 1 calc R U . . .
H11B H 1.050203 0.410511 0.930716 0.050 Uiso 1 1 calc R U . . .
C12 C 0.8828(9) 0.3809(5) 1.0271(6) 0.041(2) Uani 1 1 d . . . . .
H12A H 0.950387 0.339147 1.058476 0.049 Uiso 1 1 calc R U . . .
H12B H 0.885941 0.433785 1.065038 0.049 Uiso 1 1 calc R U . . .
C13 C 0.5128(10) 0.3754(5) 0.9146(5) 0.039(2) Uani 1 1 d . . . . .
H13A H 0.438745 0.336673 0.944561 0.047 Uiso 1 1 calc R U . . .
H13B H 0.455189 0.421761 0.883478 0.047 Uiso 1 1 calc R U . . .
C14 C 0.6146(9) 0.4122(5) 0.9906(6) 0.037(2) Uani 1 1 d . . . . .
H14A H 0.669903 0.461489 0.964430 0.044 Uiso 1 1 calc R U . . .
H14B H 0.552182 0.432129 1.044547 0.044 Uiso 1 1 calc R U . . .
C15 C 0.6830(10) 0.3166(6) 1.1205(5) 0.042(2) Uani 1 1 d . . . . .
H15A H 0.691094 0.362917 1.166801 0.063 Uiso 1 1 calc R U . . .
H15B H 0.751154 0.270471 1.139430 0.063 Uiso 1 1 calc R U . . .
H15C H 0.578182 0.295828 1.118553 0.063 Uiso 1 1 calc R U . . .
Cl1 Cl 0.7435(3) 0.6584(3) 0.8987(2) 0.0833(15) Uani 0.807(3) 1 d . . P A 1
Cl1A Cl 0.743(2) 0.7195(11) 0.9263(12) 0.024(4) Uiso 0.110(3) 1 d . . P B 2
Cl1B Cl 0.700(3) 0.5911(18) 0.855(2) 0.048(8) Uiso 0.082(3) 1 d . . P C 3
Cl2 Cl 0.2590(10) 0.9722(4) 0.7923(4) 0.021(2) Uani 0.552(10) 1 d . . P D 1
Cl2A Cl 0.2478(14) 0.9741(8) 0.7980(9) 0.070(6) Uani 0.448(10) 1 d D . P D 2
O1 O 0.2503(16) 1.0144(7) 0.8742(8) 0.056(5) Uani 0.448(10) 1 d D U P D 2
O2 O 0.2699(14) 0.8967(7) 0.8049(8) 0.042(4) Uani 0.448(10) 1 d D . P D 2
O3 O 0.1116(17) 0.9842(10) 0.7671(11) 0.114(6) Uani 0.448(10) 1 d D U P D 2
O4 O 0.333(2) 1.0047(9) 0.7365(10) 0.100(8) Uani 0.448(10) 1 d D . P D 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0076 0.0040 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'
O O 0.0132 0.0074 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'
Cl Cl 0.1697 0.1896 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'
Cu Cu 0.2913 1.4803 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N3 152.3(2) . . ?
N1 Cu1 N2 86.3(2) . . ?
N3 Cu1 N2 87.9(2) . . ?
N1 Cu1 N4 86.2(3) . . ?
N3 Cu1 N4 87.3(3) . . ?
N2 Cu1 N4 154.1(2) . . ?
N1 Cu1 N5 84.7(2) . . ?
N3 Cu1 N5 121.5(2) . . ?
N2 Cu1 N5 119.2(2) . . ?
N4 Cu1 N5 84.7(2) . . ?
C13 N1 C1 113.7(6) . . ?
C13 N1 C10 112.0(6) . . ?
C1 N1 C10 111.7(6) . . ?
C13 N1 Cu1 105.6(4) . . ?
C1 N1 Cu1 104.1(4) . . ?
C10 N1 Cu1 109.2(5) . . ?
C3 N2 C2 109.6(6) . . ?
C3 N2 C4 111.7(6) . . ?
C2 N2 C4 111.0(6) . . ?
C3 N2 Cu1 117.0(5) . . ?
C2 N2 Cu1 108.0(5) . . ?
C4 N2 Cu1 99.2(4) . . ?
C7 N3 C6 109.8(6) . . ?
C7 N3 C5 112.1(6) . . ?
C6 N3 C5 109.4(6) . . ?
C7 N3 Cu1 100.0(5) . . ?
C6 N3 Cu1 119.2(5) . . ?
C5 N3 Cu1 106.0(5) . . ?
C8 N4 C11 113.1(6) . . ?
C8 N4 C9 111.4(6) . . ?
C11 N4 C9 113.0(6) . . ?
C8 N4 Cu1 106.4(5) . . ?
C11 N4 Cu1 109.9(5) . . ?
C9 N4 Cu1 102.3(5) . . ?
C15 N5 C12 110.4(6) . . ?
C15 N5 C14 110.6(6) . . ?
C12 N5 C14 112.1(6) . . ?
C15 N5 Cu1 115.7(5) . . ?
C12 N5 Cu1 101.4(4) . . ?
C14 N5 Cu1 106.4(4) . . ?
N1 C1 C2 110.3(6) . . ?
N2 C2 C1 111.5(7) . . ?
N2 C4 C5 110.1(6) . . ?
N3 C5 C4 110.9(6) . . ?
N3 C7 C8 110.3(6) . . ?
N4 C8 C7 110.3(7) . . ?
N4 C9 C10 109.7(6) . . ?
N1 C10 C9 109.9(6) . . ?
N4 C11 C12 111.6(6) . . ?
N5 C12 C11 111.5(6) . . ?
N1 C13 C14 112.1(7) . . ?
N5 C14 C13 110.9(6) . . ?
O2 Cl2A O1 115.7(11) . . ?
O2 Cl2A O4 109.9(11) . . ?
O1 Cl2A O4 112.9(11) . . ?
O2 Cl2A O3 107.1(11) . . ?
O1 Cl2A O3 103.8(11) . . ?
O4 Cl2A O3 106.6(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 2.013(6) . ?
Cu1 N3 2.034(6) . ?
Cu1 N2 2.035(6) . ?
Cu1 N4 2.042(6) . ?
Cu1 N5 2.162(6) . ?
N1 C13 1.467(9) . ?
N1 C1 1.486(9) . ?
N1 C10 1.508(9) . ?
N2 C3 1.475(9) . ?
N2 C2 1.486(9) . ?
N2 C4 1.491(9) . ?
N3 C7 1.485(9) . ?
N3 C6 1.488(9) . ?
N3 C5 1.491(10) . ?
N4 C8 1.479(9) . ?
N4 C11 1.481(9) . ?
N4 C9 1.494(9) . ?
N5 C15 1.474(9) . ?
N5 C12 1.477(9) . ?
N5 C14 1.493(9) . ?
C1 C2 1.487(11) . ?
C4 C5 1.507(11) . ?
C7 C8 1.497(11) . ?
C9 C10 1.521(11) . ?
C11 C12 1.509(11) . ?
C13 C14 1.505(11) . ?
Cl2A O2 1.242(12) . ?
Cl2A O1 1.243(11) . ?
Cl2A O4 1.246(13) . ?
Cl2A O3 1.283(14) . ?
