#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:18:03 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272603 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/38/7243817.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_7243817
loop_
_publ_author_name
'Verma, Abhineet'
'Bhuvanesh, Nattamai'
'Reibenspies, Joseph'
'Tayade, Sakharam B.'
'Kumbhar, Avinash S.'
'Bretosh, Kateryna'
'Sutter, Jean-Pascal'
'Sunkari, Sailaja S.'
_publ_section_title
;
 Structurally characterised new twisted conformer for cyclen, controlled
 by metal ion complexation as seen in NiII and CuII complexes with halides
 and pseudohalides
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              119
_journal_page_last               131
_journal_paper_doi               10.1039/D1CE01096D
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'Br, C10 H23 N4 Ni O2'
_chemical_formula_sum            'C10 H23 Br N4 Ni O2'
_chemical_formula_weight         369.94
_chemical_melting_point          455.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-27 deposited with the CCDC.	2021-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1276(11)
_cell_length_b                   8.9116(7)
_cell_length_c                   11.1889(8)
_cell_measurement_reflns_used    9805
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.471
_cell_measurement_theta_min      2.264
_cell_volume                     1508.39(19)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.0
_diffrn_detector                 'Bruker PHOTON 2 area detector'
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Charge-integrating Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker Photon 2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27328
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         2.264
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    3.936
_exptl_absorpt_correction_T_max  0.4305
_exptl_absorpt_correction_T_min  0.1797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1374 before and 0.0789 after correction. The Ratio of minimum to maximum transmission is 0.4174. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method
'Ether diffusion into methnolic mother liquor'
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.186
_refine_diff_density_max         1.200
_refine_diff_density_min         -0.862
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1848
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.190
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0434
_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/[σ²(Fo²)+(0.0124P)²+7.5439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0862
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1602
_reflns_number_total             1848
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01096d2.cif
_cod_data_source_block           ssr2a
_cod_depositor_comments
'Adding full bibliography for 7243811--7243817.cif.'
_cod_database_code               7243817
_shelx_shelxl_version_number     2018/3
_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_max   0.528
_shelx_estimated_absorpt_t_min   0.448
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.002
3. Others
 Fixed Sof: H6B(0.5) H6A(0.5)
4.a Ternary CH refined with riding coordinates:
 N3(H3), N1(H1), N2(H2)
4.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
4.c Me refined with riding coordinates:
 C6(H6C,H6B,H6A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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
Br1 Br 0.11841(3) 0.750000 0.80255(5) 0.01605(14) Uani 1 2 d S T P . .
Ni1 Ni 0.33767(4) 0.750000 0.48374(6) 0.01020(16) Uani 1 2 d S T P . .
O2 O 0.4509(2) 0.750000 0.3788(3) 0.0163(8) Uani 1 2 d S T P . .
O1 O 0.3204(2) 0.750000 0.2924(3) 0.0159(8) Uani 1 2 d S T P . .
N3 N 0.3970(3) 0.750000 0.6470(4) 0.0135(9) Uani 1 2 d S T P . .
H3 H 0.462530 0.750001 0.634902 0.016 Uiso 1 2 calc R U P . .
N1 N 0.2054(3) 0.750000 0.5276(4) 0.0136(9) Uani 1 2 d S T P . .
H1 H 0.197346 0.750001 0.616324 0.016 Uiso 1 2 calc R U P . .
N2 N 0.3244(2) 0.5173(3) 0.5107(3) 0.0169(7) Uani 1 1 d . . . . .
H2 H 0.348162 0.461893 0.439915 0.020 Uiso 1 1 calc R U . . .
C5 C 0.4042(3) 0.750000 0.2853(5) 0.0183(11) Uani 1 2 d S T P . .
C4 C 0.3722(2) 0.6099(4) 0.7082(3) 0.0180(8) Uani 1 1 d . . . . .
H4A H 0.311271 0.617653 0.739721 0.022 Uiso 1 1 calc R U . . .
H4B H 0.412786 0.590823 0.775956 0.022 Uiso 1 1 calc R U . . .
C1 C 0.1730(2) 0.6094(4) 0.4754(3) 0.0181(8) Uani 1 1 d . . . . .
H1A H 0.178383 0.612439 0.387249 0.022 Uiso 1 1 calc R U . . .
H1B H 0.109995 0.594107 0.496181 0.022 Uiso 1 1 calc R U . . .
C2 C 0.2287(3) 0.4832(4) 0.5259(4) 0.0201(8) Uani 1 1 d . . . . .
H2A H 0.215277 0.470133 0.611892 0.024 Uiso 1 1 calc R U . . .
H2B H 0.214284 0.388314 0.484299 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3782(3) 0.4822(4) 0.6177(3) 0.0215(8) Uani 1 1 d . . . . .
H3A H 0.440612 0.467092 0.593938 0.026 Uiso 1 1 calc R U . . .
H3B H 0.356643 0.388060 0.654600 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4489(4) 0.750000 0.1655(6) 0.0348(15) Uani 1 2 d S TU P . .
H6C H 0.404097 0.750000 0.102272 0.052 Uiso 1 2 calc R U P . .
H6B H 0.485904 0.839789 0.158035 0.052 Uiso 0.5 1 calc R U P . .
H6A H 0.485904 0.660211 0.158035 0.052 Uiso 0.5 1 calc R U P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O2 Ni1 O1 62.52(13) . . ?
O2 Ni1 N2 99.17(9) . 7_575 ?
O2 Ni1 N2 99.17(9) . . ?
O2 Ni1 C5 31.17(15) . . ?
O1 Ni1 C5 31.35(15) . . ?
N3 Ni1 O2 98.25(15) . . ?
N3 Ni1 O1 160.78(15) . . ?
N3 Ni1 N1 102.40(17) . . ?
N3 Ni1 N2 85.03(9) . 7_575 ?
N3 Ni1 N2 85.03(9) . . ?
N3 Ni1 C5 129.42(17) . . ?
N1 Ni1 O2 159.35(16) . . ?
N1 Ni1 O1 96.83(15) . . ?
N1 Ni1 N2 82.74(9) . 7_575 ?
N1 Ni1 N2 82.74(9) . . ?
N1 Ni1 C5 128.18(17) . . ?
N2 Ni1 O1 97.51(9) 7_575 . ?
N2 Ni1 O1 97.51(9) . . ?
N2 Ni1 N2 160.20(17) 7_575 . ?
N2 Ni1 C5 99.78(9) 7_575 . ?
N2 Ni1 C5 99.77(9) . . ?
C5 O2 Ni1 90.4(3) . . ?
C5 O1 Ni1 86.6(3) . . ?
Ni1 N3 H3 108.4 . . ?
C4 N3 Ni1 107.7(2) 7_575 . ?
C4 N3 Ni1 107.7(2) . . ?
C4 N3 H3 108.4 . . ?
C4 N3 H3 108.4 7_575 . ?
C4 N3 C4 116.0(4) . 7_575 ?
Ni1 N1 H1 110.8 . . ?
C1 N1 Ni1 103.3(2) 7_575 . ?
C1 N1 Ni1 103.3(2) . . ?
C1 N1 H1 110.8 . . ?
C1 N1 H1 110.8 7_575 . ?
C1 N1 C1 117.3(4) 7_575 . ?
Ni1 N2 H2 109.8 . . ?
C2 N2 Ni1 108.0(2) . . ?
C2 N2 H2 109.8 . . ?
C3 N2 Ni1 105.8(2) . . ?
C3 N2 H2 109.8 . . ?
C3 N2 C2 113.5(3) . . ?
O2 C5 Ni1 58.4(3) . . ?
O2 C5 O1 120.4(5) . . ?
O2 C5 C6 119.3(5) . . ?
O1 C5 Ni1 62.0(3) . . ?
O1 C5 C6 120.3(5) . . ?
C6 C5 Ni1 177.6(4) . . ?
N3 C4 H4A 110.1 . . ?
N3 C4 H4B 110.1 . . ?
N3 C4 C3 108.0(3) . . ?
H4A C4 H4B 108.4 . . ?
C3 C4 H4A 110.1 . . ?
C3 C4 H4B 110.1 . . ?
N1 C1 H1A 110.2 . . ?
N1 C1 H1B 110.2 . . ?
N1 C1 C2 107.4(3) . . ?
H1A C1 H1B 108.5 . . ?
C2 C1 H1A 110.2 . . ?
C2 C1 H1B 110.2 . . ?
N2 C2 C1 110.3(3) . . ?
N2 C2 H2A 109.6 . . ?
N2 C2 H2B 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
N2 C3 C4 110.3(3) . . ?
N2 C3 H3A 109.6 . . ?
N2 C3 H3B 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C5 C6 H6C 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6A 109.5 . . ?
H6C C6 H6B 109.5 . . ?
H6C C6 H6A 109.5 . . ?
H6B C6 H6A 109.5 . . ?
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
Ni1 O2 2.076(4) . ?
Ni1 O1 2.157(4) . ?
Ni1 N3 2.036(4) . ?
Ni1 N1 2.060(4) . ?
Ni1 N2 2.105(3) . ?
Ni1 N2 2.105(3) 7_575 ?
Ni1 C5 2.438(5) . ?
O2 C5 1.262(6) . ?
O1 C5 1.271(6) . ?
N3 H3 1.0000 . ?
N3 C4 1.472(4) 7_575 ?
N3 C4 1.472(4) . ?
N1 H1 1.0000 . ?
N1 C1 1.467(4) . ?
N1 C1 1.467(4) 7_575 ?
N2 H2 1.0000 . ?
N2 C2 1.489(5) . ?
N2 C3 1.481(5) . ?
C5 C6 1.501(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.526(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.515(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C6 H6C 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6A 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 O2 C5 O1 0.000(0) . . . . ?
Ni1 O2 C5 C6 180.000(0) . . . . ?
Ni1 O1 C5 O2 0.000(0) . . . . ?
Ni1 O1 C5 C6 180.000(0) . . . . ?
Ni1 N3 C4 C3 42.9(3) . . . . ?
Ni1 N1 C1 C2 55.9(3) . . . . ?
Ni1 N2 C2 C1 19.8(4) . . . . ?
Ni1 N2 C3 C4 36.2(3) . . . . ?
N3 C4 C3 N2 -54.2(4) . . . . ?
N1 C1 C2 N2 -51.5(4) . . . . ?
C4 N3 C4 C3 163.7(3) 7_575 . . . ?
C1 N1 C1 C2 168.7(3) 7_575 . . . ?
C2 N2 C3 C4 -82.0(4) . . . . ?
C3 N2 C2 C1 136.7(3) . . . . ?
