#------------------------------------------------------------------------------
#$Date: 2020-12-06 10:47:00 +0200 (Sun, 06 Dec 2020) $
#$Revision: 259596 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/16/7241696.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_7241696
loop_
_publ_author_name
'Peewasan, Krisana'
'Merkel, Marcel P.'
'Fuhr, Olaf'
'Anson, Christopher E.'
'Powell, Annie K.'
_publ_section_title
;
 A multifunctional use of bis(methylene)bis(5-bromo-2-hydroxyl
 salicyloylhydrazone): from metal sensing to ambient catalysis of A3
 coupling reactions
;
_journal_issue                   67
_journal_name_full               'RSC Advances'
_journal_page_first              40739
_journal_page_last               40744
_journal_paper_doi               10.1039/D0RA07687B
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety
'C34 H33 Br2 Cu2 N8 O12, 0.5(H2 O), N O3, 2(C2 H3 N)'
_chemical_formula_sum            'C38 H40 Br2 Cu2 N11 O15.5'
_chemical_formula_weight         1185.71
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-10-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-06 deposited with the CCDC.	2020-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                109.496(3)
_cell_angle_beta                 94.616(3)
_cell_angle_gamma                99.025(3)
_cell_formula_units_Z            2
_cell_length_a                   9.3905(4)
_cell_length_b                   14.9547(6)
_cell_length_c                   17.6271(6)
_cell_measurement_reflns_used    19644
_cell_measurement_temperature    180
_cell_measurement_theta_max      64.14
_cell_measurement_theta_min      2.34
_cell_volume                     2281.02(16)
_computing_cell_refinement
;
X-Area Recipe 1.34.0.0 (STOE, 2019)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.154.0 (STOE, 2019)
;
_computing_data_reduction
;
X-Area Integrate 1.77.0.0 (STOE, 2019)
X-Area LANA 1.77.1.0 (STOE, 2019)
;
_computing_molecular_graphics    'Diamond 4 (Crystal Impact, 2017)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 13.33
_diffrn_detector_type            DECTRIS
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34143
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23734
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        53.597
_diffrn_reflns_theta_max         58.104
_diffrn_reflns_theta_min         4.190
_diffrn_source_target            Ga
_diffrn_source_type              'Metaljet D2'
_exptl_absorpt_coefficient_mu    6.914
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.2795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_description       needle
_exptl_crystal_F_000             1194
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     664
_refine_ls_number_reflns         9418
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0426
_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/[σ²(Fo²)+(0.0653P)²+0.2616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1150
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6929
_reflns_number_total             9418
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra07687b2.cif
_cod_data_source_block           kp439-re
_cod_database_code               7241696
_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   0.874
_shelx_estimated_absorpt_t_min   0.444
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O1-H1 = O6-H6
 0.88 with sigma of 0.04
 N3-H3 = N4-H4 = N1-H1A
 0.84 with sigma of 0.04
 O16-H16D = O16-H16C
 0.88 with sigma of 0.04
 O11B-N8 \\sim O10B-N8
 with sigma of 0.02
 O10B-O11B \\sim O11B-O12B \\sim O12B-O10B
 with sigma of 0.02
 O12A-N8 \\sim O12B-N8
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O12A \\sim O12B: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
4. Others
 Fixed Sof: O10A(0.78) O10B(0.22) O11A(0.78) O11B(0.22) O12A(0.78) O12B(0.22)
 O16(0.5) H16C(0.5) H16D(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C20(H20A,H20B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4A), C5(H5), C8(H8), C12(H12), C14(H14), C24(H24),
 C26(H26), C27(H27), C31(H31), C32(H32), C33(H33), C34(H34)
5.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C36(H36A,H36B,H36C), C38(H38A,H38B,
 H38C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.52746(5) 0.37292(3) 0.21721(2) 0.04254(12) Uani 1 1 d . . . . .
Br2 Br 0.45293(6) 0.45656(3) -0.41641(3) 0.05348(14) Uani 1 1 d . . . . .
Cu1 Cu 0.60416(5) -0.01069(4) -0.15958(3) 0.02732(13) Uani 1 1 d . . . . .
Cu2 Cu 0.58192(6) 0.01275(4) -0.35449(3) 0.02846(13) Uani 1 1 d . . . . .
O1 O 0.9436(3) -0.1570(2) 0.0014(2) 0.0532(8) Uani 1 1 d D . . . .
H1 H 1.000(5) -0.135(4) 0.045(2) 0.075(18) Uiso 1 1 d D . . . .
O2 O 0.7023(3) -0.12172(17) -0.18788(14) 0.0341(5) Uani 1 1 d . . . . .
O3 O 0.4963(2) 0.08843(16) -0.12185(13) 0.0287(5) Uani 1 1 d . . . . .
O4 O 0.4850(3) 0.11622(16) -0.31156(14) 0.0308(5) Uani 1 1 d . . . . .
O5 O 0.6788(3) -0.09186(17) -0.40465(14) 0.0341(5) Uani 1 1 d . . . . .
O6 O 0.8970(3) -0.0575(2) -0.59610(16) 0.0413(6) Uani 1 1 d D . . . .
H6 H 0.830(5) -0.025(4) -0.572(3) 0.085(19) Uiso 1 1 d D . . . .
O7 O 0.5123(3) -0.04503(17) -0.27371(14) 0.0312(5) Uani 1 1 d . . . . .
O8 O 0.3333(3) -0.1344(2) -0.24701(18) 0.0595(8) Uani 1 1 d . . . . .
O9 O 0.3223(3) -0.1153(2) -0.36428(17) 0.0596(8) Uani 1 1 d . . . . .
O10A O 0.7662(4) 0.0671(2) -0.2225(2) 0.0421(8) Uani 0.78 1 d . . P A 1
O10B O 0.8042(13) 0.1226(9) -0.2522(7) 0.047(3) Uiso 0.22 1 d D . P A 2
O11A O 0.8498(4) 0.1703(3) -0.1036(2) 0.0451(8) Uani 0.78 1 d . . P A 1
O11B O 0.8222(16) 0.1041(12) -0.1376(9) 0.059(4) Uiso 0.22 1 d D . P A 2
O12A O 0.9684(5) 0.1724(4) -0.2030(4) 0.0648(13) Uani 0.78 1 d D U P A 1
O12B O 0.978(2) 0.2026(17) -0.1625(12) 0.104(10) Uiso 0.22 1 d D U P A 2
N1 N 0.7719(3) -0.0653(2) -0.0534(2) 0.0307(6) Uani 1 1 d D . . . .
H1A H 0.811(4) -0.062(3) -0.013(2) 0.039(12) Uiso 1 1 d D . . . .
N2 N 0.6892(3) 0.0042(2) -0.05163(17) 0.0272(6) Uani 1 1 d . . . . .
N3 N 0.4093(3) 0.2406(2) -0.16541(16) 0.0245(6) Uani 1 1 d D . . . .
H3 H 0.456(3) 0.199(2) -0.1821(19) 0.013(8) Uiso 1 1 d D . . . .
N4 N 0.7660(3) 0.4137(2) -0.1387(2) 0.0381(7) Uani 1 1 d D . . . .
H4 H 0.752(5) 0.457(3) -0.093(2) 0.044(12) Uiso 1 1 d D . . . .
N5 N 0.6545(3) 0.0576(2) -0.43631(16) 0.0284(6) Uani 1 1 d . . . . .
N6 N 0.7360(3) -0.0010(2) -0.48437(17) 0.0306(6) Uani 1 1 d . . . . .
N7 N 0.3827(4) -0.1011(2) -0.29615(19) 0.0400(7) Uani 1 1 d . . . . .
N8 N 0.8631(4) 0.1377(2) -0.1810(2) 0.0422(8) Uani 1 1 d D . . . .
C1 C 0.9480(4) -0.2156(3) -0.0749(2) 0.0393(9) Uani 1 1 d . . . . .
C2 C 1.0352(4) -0.2852(3) -0.0918(3) 0.0470(11) Uani 1 1 d . . . . .
H2 H 1.092850 -0.293426 -0.048719 0.056 Uiso 1 1 calc R . . . .
C3 C 1.0377(5) -0.3419(3) -0.1709(3) 0.0510(11) Uani 1 1 d . . . . .
H3A H 1.100874 -0.387109 -0.181976 0.061 Uiso 1 1 calc R . . . .
C4 C 0.9502(5) -0.3347(3) -0.2348(3) 0.0516(11) Uani 1 1 d . . . . .
H4A H 0.950142 -0.375999 -0.289073 0.062 Uiso 1 1 calc R . . . .
C5 C 0.8633(4) -0.2665(3) -0.2182(3) 0.0408(9) Uani 1 1 d . . . . .
H5 H 0.802892 -0.261354 -0.261805 0.049 Uiso 1 1 calc R . . . .
C6 C 0.8611(4) -0.2048(3) -0.1391(2) 0.0346(8) Uani 1 1 d . . . . .
C7 C 0.7741(4) -0.1287(3) -0.1274(2) 0.0327(8) Uani 1 1 d . . . . .
C8 C 0.6793(4) 0.0689(2) 0.0165(2) 0.0291(7) Uani 1 1 d . . . . .
H8 H 0.730618 0.068368 0.064962 0.035 Uiso 1 1 calc R . . . .
C9 C 0.5931(4) 0.1423(2) 0.02216(19) 0.0262(7) Uani 1 1 d . . . . .
C10 C 0.5057(3) 0.1467(2) -0.04631(19) 0.0253(7) Uani 1 1 d . . . . .
C11 C 0.4216(3) 0.2200(2) -0.03095(19) 0.0250(7) Uani 1 1 d . . . . .
C12 C 0.4280(4) 0.2862(2) 0.0459(2) 0.0297(7) Uani 1 1 d . . . . .
H12 H 0.372123 0.335543 0.054680 0.036 Uiso 1 1 calc R . . . .
C13 C 0.5166(4) 0.2807(2) 0.1112(2) 0.0314(8) Uani 1 1 d . . . . .
C14 C 0.5962(4) 0.2103(2) 0.0995(2) 0.0293(7) Uani 1 1 d . . . . .
H14 H 0.654999 0.207090 0.144592 0.035 Uiso 1 1 calc R . . . .
C15 C 0.3230(3) 0.2229(2) -0.10117(19) 0.0258(7) Uani 1 1 d . . . . .
H15A H 0.267141 0.275014 -0.081355 0.031 Uiso 1 1 calc R . . . .
H15B H 0.252617 0.160728 -0.125428 0.031 Uiso 1 1 calc R . . . .
C16 C 0.5187(3) 0.3334(2) -0.1323(2) 0.0272(7) Uani 1 1 d . . . . .
H16A H 0.524626 0.359665 -0.072356 0.033 Uiso 1 1 calc R . . . .
H16B H 0.486200 0.381081 -0.153995 0.033 Uiso 1 1 calc R . . . .
C17 C 0.6682(4) 0.3193(3) -0.1545(2) 0.0337(8) Uani 1 1 d . . . . .
H17A H 0.711016 0.284634 -0.122263 0.040 Uiso 1 1 calc R . . . .
H17B H 0.658934 0.279206 -0.212781 0.040 Uiso 1 1 calc R . . . .
C18 C 0.9222(4) 0.4033(4) -0.1368(3) 0.0602(13) Uani 1 1 d . . . . .
H18A H 0.947329 0.376069 -0.095245 0.090 Uiso 1 1 calc GR . . . .
H18B H 0.984685 0.466970 -0.123834 0.090 Uiso 1 1 calc GR . . . .
H18C H 0.936738 0.360195 -0.190070 0.090 Uiso 1 1 calc GR . . . .
C19 C 0.7271(5) 0.4601(4) -0.1977(4) 0.0694(15) Uani 1 1 d . . . . .
H19A H 0.736675 0.418523 -0.252610 0.104 Uiso 1 1 calc GR . . . .
H19B H 0.792488 0.522865 -0.183690 0.104 Uiso 1 1 calc GR . . . .
H19C H 0.626256 0.469454 -0.195895 0.104 Uiso 1 1 calc GR . . . .
C20 C 0.3083(4) 0.2358(2) -0.23862(19) 0.0280(7) Uani 1 1 d . . . . .
H20A H 0.244393 0.170957 -0.261794 0.034 Uiso 1 1 calc R . . . .
H20B H 0.245638 0.284240 -0.221339 0.034 Uiso 1 1 calc R . . . .
C21 C 0.3916(4) 0.2546(2) -0.3026(2) 0.0277(7) Uani 1 1 d . . . . .
C22 C 0.4774(4) 0.1868(2) -0.3401(2) 0.0277(7) Uani 1 1 d . . . . .
C23 C 0.5537(4) 0.2013(2) -0.40293(19) 0.0273(7) Uani 1 1 d . . . . .
C24 C 0.5437(4) 0.2828(3) -0.4242(2) 0.0349(8) Uani 1 1 d . . . . .
H24 H 0.594559 0.293188 -0.465925 0.042 Uiso 1 1 calc R . . . .
C25 C 0.4616(4) 0.3474(3) -0.3856(2) 0.0360(8) Uani 1 1 d . . . . .
C26 C 0.3841(4) 0.3339(2) -0.3247(2) 0.0309(7) Uani 1 1 d . . . . .
H26 H 0.326680 0.378965 -0.298792 0.037 Uiso 1 1 calc R . . . .
C27 C 0.6382(4) 0.1356(2) -0.4485(2) 0.0298(7) Uani 1 1 d . . . . .
H27 H 0.684550 0.150612 -0.489916 0.036 Uiso 1 1 calc R . . . .
C28 C 0.7427(4) -0.0767(3) -0.4628(2) 0.0303(7) Uani 1 1 d . . . . .
C29 C 0.8311(4) -0.1456(3) -0.5071(2) 0.0328(8) Uani 1 1 d . . . . .
C30 C 0.9047(4) -0.1317(3) -0.5703(2) 0.0354(8) Uani 1 1 d . . . . .
C31 C 0.9868(4) -0.1985(3) -0.6100(2) 0.0426(9) Uani 1 1 d . . . . .
H31 H 1.037415 -0.189077 -0.652136 0.051 Uiso 1 1 calc R . . . .
C32 C 0.9946(5) -0.2778(3) -0.5883(3) 0.0493(10) Uani 1 1 d . . . . .
H32 H 1.050847 -0.322911 -0.615668 0.059 Uiso 1 1 calc R . . . .
C33 C 0.9213(5) -0.2932(3) -0.5269(3) 0.0485(10) Uani 1 1 d . . . . .
H33 H 0.926598 -0.348735 -0.512792 0.058 Uiso 1 1 calc R . . . .
C34 C 0.8410(4) -0.2272(3) -0.4868(2) 0.0400(9) Uani 1 1 d . . . . .
H34 H 0.791550 -0.237384 -0.444564 0.048 Uiso 1 1 calc R . . . .
O16 O 0.5537(10) -0.2615(6) -0.3685(5) 0.076(2) Uani 0.5 1 d D . P . .
H16C H 0.602(14) -0.253(10) -0.322(5) 0.115 Uiso 0.5 1 d DR . P . .
H16D H 0.616(12) -0.228(9) -0.388(8) 0.115 Uiso 0.5 1 d DR . P . .
O13 O 0.7154(4) 0.5427(2) 0.0066(2) 0.0640(9) Uani 1 1 d . . . . .
O14 O 0.7749(4) 0.4226(2) 0.03288(18) 0.0558(8) Uani 1 1 d . . . . .
O15 O 0.7370(4) 0.5452(3) 0.1300(2) 0.0662(9) Uani 1 1 d . . . . .
N9 N 0.7416(3) 0.5028(2) 0.0582(2) 0.0443(8) Uani 1 1 d . . . . .
N10 N 1.1001(4) -0.0076(3) -0.1372(2) 0.0497(9) Uani 1 1 d . . . . .
C35 C 1.0578(4) -0.0361(3) -0.2045(3) 0.0390(9) Uani 1 1 d . . . . .
C36 C 1.0004(5) -0.0728(3) -0.2910(3) 0.0509(10) Uani 1 1 d . . . . .
H36A H 1.028056 -0.135152 -0.317424 0.076 Uiso 1 1 calc GR . . . .
H36B H 1.040602 -0.026585 -0.315903 0.076 Uiso 1 1 calc GR . . . .
H36C H 0.893937 -0.081178 -0.297641 0.076 Uiso 1 1 calc GR . . . .
N11 N 0.1403(7) -0.4814(5) -0.5672(5) 0.114(2) Uani 1 1 d . . . . .
C37 C 0.1719(7) -0.4331(5) -0.4988(5) 0.0814(17) Uani 1 1 d . . . . .
C38 C 0.2116(8) -0.3715(5) -0.4136(4) 0.0884(18) Uani 1 1 d . . . . .
H38A H 0.160382 -0.317208 -0.402281 0.133 Uiso 1 1 calc GR . . . .
H38B H 0.316949 -0.346769 -0.402176 0.133 Uiso 1 1 calc GR . . . .
H38C H 0.184044 -0.409150 -0.379169 0.133 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0150 0.0070 '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 -0.9500 1.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -2.9180 3.6940 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0410 0.0250 '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 Cu1 O7 92.56(10) . . ?
O2 Cu1 O10A 90.30(11) . . ?
O2 Cu1 O11B 93.9(4) . . ?
O3 Cu1 O2 171.60(10) . . ?
O3 Cu1 O7 91.76(9) . . ?
O3 Cu1 O10A 97.85(11) . . ?
O3 Cu1 O11B 91.6(4) . . ?
O3 Cu1 N2 93.81(10) . . ?
O7 Cu1 O10A 72.98(11) . . ?
O7 Cu1 O11B 108.0(3) . . ?
N2 Cu1 O2 81.25(11) . . ?
N2 Cu1 O7 172.28(10) . . ?
N2 Cu1 O10A 111.45(11) . . ?
N2 Cu1 O11B 77.2(3) . . ?
O4 Cu2 O5 176.49(9) . . ?
O4 Cu2 O7 90.04(9) . . ?
O4 Cu2 O10A 92.38(11) . . ?
O4 Cu2 O10B 85.4(3) . . ?
O4 Cu2 N5 95.01(11) . . ?
O5 Cu2 O7 92.99(10) . . ?
O5 Cu2 O10A 90.44(11) . . ?
O5 Cu2 O10B 96.3(3) . . ?
O7 Cu2 O10A 67.20(10) . . ?
O7 Cu2 O10B 91.9(3) . . ?
N5 Cu2 O5 81.94(11) . . ?
N5 Cu2 O7 174.89(11) . . ?
N5 Cu2 O10A 113.27(11) . . ?
N5 Cu2 O10B 89.3(3) . . ?
C1 O1 H1 136(4) . . ?
C7 O2 Cu1 113.2(2) . . ?
C10 O3 Cu1 125.90(19) . . ?
C22 O4 Cu2 125.5(2) . . ?
C28 O5 Cu2 110.2(2) . . ?
C30 O6 H6 110(4) . . ?
Cu1 O7 Cu2 126.65(13) . . ?
N7 O7 Cu1 117.63(19) . . ?
N7 O7 Cu2 115.00(19) . . ?
Cu1 O10A Cu2 92.31(11) . . ?
N8 O10A Cu1 120.6(3) . . ?
N8 O10A Cu2 139.0(3) . . ?
N8 O10B Cu2 139.1(8) . . ?
N8 O11B Cu1 126.9(10) . . ?
N2 N1 H1A 117(3) . . ?
C7 N1 H1A 128(3) . . ?
C7 N1 N2 114.9(3) . . ?
N1 N2 Cu1 111.5(2) . . ?
C8 N2 Cu1 128.3(2) . . ?
C8 N2 N1 120.2(3) . . ?
C15 N3 H3 111(2) . . ?
C16 N3 H3 105(2) . . ?
C16 N3 C15 112.0(3) . . ?
C16 N3 C20 112.0(2) . . ?
C20 N3 H3 106(2) . . ?
C20 N3 C15 110.6(2) . . ?
C17 N4 H4 111(3) . . ?
C17 N4 C18 111.1(3) . . ?
C18 N4 H4 111(3) . . ?
C19 N4 H4 100(3) . . ?
C19 N4 C17 112.6(3) . . ?
C19 N4 C18 110.7(4) . . ?
N6 N5 Cu2 114.0(2) . . ?
C27 N5 Cu2 127.2(2) . . ?
C27 N5 N6 118.7(3) . . ?
C28 N6 N5 110.5(3) . . ?
O8 N7 O7 117.1(3) . . ?
O9 N7 O7 117.0(3) . . ?
O9 N7 O8 125.9(3) . . ?
O10A N8 O11A 113.7(4) . . ?
O10B N8 O12B 110.0(9) . . ?
O11B N8 O10B 127.4(9) . . ?
O11B N8 O12B 122.6(10) . . ?
O12A N8 O10A 127.5(5) . . ?
O12A N8 O11A 118.6(4) . . ?
O1 C1 C2 122.2(4) . . ?
O1 C1 C6 118.0(3) . . ?
C2 C1 C6 119.8(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3A 119.3 . . ?
C2 C3 C4 121.4(4) . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 C3 118.7(4) . . ?
C5 C4 H4A 120.6 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 121.9(4) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C7 123.4(3) . . ?
C5 C6 C1 118.2(3) . . ?
C5 C6 C7 118.3(3) . . ?
O2 C7 N1 119.1(3) . . ?
O2 C7 C6 119.9(3) . . ?
N1 C7 C6 121.0(3) . . ?
N2 C8 H8 118.7 . . ?
N2 C8 C9 122.7(3) . . ?
C9 C8 H8 118.7 . . ?
C10 C9 C8 123.3(3) . . ?
C14 C9 C8 116.8(3) . . ?
C14 C9 C10 120.0(3) . . ?
O3 C10 C9 125.6(3) . . ?
O3 C10 C11 117.4(3) . . ?
C11 C10 C9 117.0(3) . . ?
C10 C11 C15 118.0(3) . . ?
C12 C11 C10 121.4(3) . . ?
C12 C11 C15 120.6(3) . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 Br1 120.0(3) . . ?
C14 C13 Br1 119.4(3) . . ?
C14 C13 C12 120.5(3) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.1(3) . . ?
C13 C14 H14 119.5 . . ?
N3 C15 H15A 109.4 . . ?
N3 C15 H15B 109.4 . . ?
C11 C15 N3 111.1(2) . . ?
C11 C15 H15A 109.4 . . ?
C11 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
N3 C16 H16A 109.3 . . ?
N3 C16 H16B 109.3 . . ?
N3 C16 C17 111.7(3) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
N4 C17 C16 111.0(3) . . ?
N4 C17 H17A 109.4 . . ?
N4 C17 H17B 109.4 . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N4 C19 H19A 109.5 . . ?
N4 C19 H19B 109.5 . . ?
N4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 H20A 109.3 . . ?
N3 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C21 C20 N3 111.5(3) . . ?
C21 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
C22 C21 C20 117.3(3) . . ?
C26 C21 C20 121.5(3) . . ?
C26 C21 C22 121.2(3) . . ?
O4 C22 C21 117.0(3) . . ?
O4 C22 C23 124.6(3) . . ?
C21 C22 C23 118.4(3) . . ?
C22 C23 C27 123.9(3) . . ?
C24 C23 C22 119.0(3) . . ?
C24 C23 C27 117.0(3) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.8(3) . . ?
C25 C24 H24 119.6 . . ?
C24 C25 Br2 119.0(3) . . ?
C24 C25 C26 121.2(3) . . ?
C26 C25 Br2 119.8(3) . . ?
C21 C26 C25 119.4(3) . . ?
C21 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
N5 C27 C23 123.5(3) . . ?
N5 C27 H27 118.2 . . ?
C23 C27 H27 118.2 . . ?
O5 C28 N6 123.2(3) . . ?
O5 C28 C29 119.4(3) . . ?
N6 C28 C29 117.3(3) . . ?
C30 C29 C28 121.7(3) . . ?
C34 C29 C28 119.5(3) . . ?
C34 C29 C30 118.8(3) . . ?
O6 C30 C29 123.0(3) . . ?
O6 C30 C31 117.4(3) . . ?
C31 C30 C29 119.6(3) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.1(4) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 119.5 . . ?
C31 C32 C33 121.0(4) . . ?
C33 C32 H32 119.5 . . ?
C32 C33 H33 120.3 . . ?
C34 C33 C32 119.3(4) . . ?
C34 C33 H33 120.3 . . ?
C29 C34 H34 119.4 . . ?
C33 C34 C29 121.2(4) . . ?
C33 C34 H34 119.4 . . ?
H16C O16 H16D 101(10) . . ?
O14 N9 O13 117.5(4) . . ?
O15 N9 O13 119.9(4) . . ?
O15 N9 O14 122.6(4) . . ?
N10 C35 C36 178.9(5) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N11 C37 C38 179.1(7) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 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
Br1 C13 1.900(3) . ?
Br2 C25 1.896(3) . ?
Cu1 O2 1.964(2) . ?
Cu1 O3 1.894(2) . ?
Cu1 O7 1.987(2) . ?
Cu1 O10A 2.339(3) . ?
Cu1 O11B 2.370(15) . ?
Cu1 N2 1.930(3) . ?
Cu2 O4 1.889(2) . ?
Cu2 O5 1.926(2) . ?
Cu2 O7 1.999(2) . ?
Cu2 O10A 2.592(3) . ?
Cu2 O10B 2.579(12) . ?
Cu2 N5 1.912(3) . ?
O1 H1 0.83(3) . ?
O1 C1 1.347(5) . ?
O2 C7 1.257(4) . ?
O3 C10 1.313(4) . ?
O4 C22 1.321(4) . ?
O5 C28 1.294(4) . ?
O6 H6 0.90(3) . ?
O6 C30 1.342(4) . ?
O7 N7 1.313(4) . ?
O8 N7 1.222(4) . ?
O9 N7 1.221(4) . ?
O10A N8 1.246(4) . ?
O10B N8 1.261(11) . ?
O11A N8 1.311(5) . ?
O11B N8 1.109(13) . ?
O12A N8 1.196(5) . ?
O12B N8 1.271(15) . ?
N1 H1A 0.75(3) . ?
N1 N2 1.385(4) . ?
N1 C7 1.336(5) . ?
N2 C8 1.288(4) . ?
N3 H3 0.81(3) . ?
N3 C15 1.514(4) . ?
N3 C16 1.495(4) . ?
N3 C20 1.513(4) . ?
N4 H4 0.88(3) . ?
N4 C17 1.484(4) . ?
N4 C18 1.498(5) . ?
N4 C19 1.482(5) . ?
N5 N6 1.375(4) . ?
N5 C27 1.283(4) . ?
N6 C28 1.316(4) . ?
C1 C2 1.394(5) . ?
C1 C6 1.409(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.372(6) . ?
C3 H3A 0.9500 . ?
C3 C4 1.385(6) . ?
C4 H4A 0.9500 . ?
C4 C5 1.375(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(6) . ?
C6 C7 1.472(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.445(5) . ?
C9 C10 1.430(4) . ?
C9 C14 1.397(5) . ?
C10 C11 1.416(4) . ?
C11 C12 1.376(5) . ?
C11 C15 1.502(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.397(5) . ?
C13 C14 1.355(5) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.515(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.499(4) . ?
C21 C22 1.417(5) . ?
C21 C26 1.376(4) . ?
C22 C23 1.424(4) . ?
C23 C24 1.403(5) . ?
C23 C27 1.436(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.367(5) . ?
C25 C26 1.396(5) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.482(5) . ?
C29 C30 1.414(5) . ?
C29 C34 1.395(5) . ?
C30 C31 1.394(5) . ?
C31 H31 0.9500 . ?
C31 C32 1.373(6) . ?
C32 H32 0.9500 . ?
C32 C33 1.391(6) . ?
C33 H33 0.9500 . ?
C33 C34 1.377(6) . ?
C34 H34 0.9500 . ?
O16 H16C 0.87(4) . ?
O16 H16D 0.88(4) . ?
O13 N9 1.271(4) . ?
O14 N9 1.233(4) . ?
O15 N9 1.219(5) . ?
N10 C35 1.131(5) . ?
C35 C36 1.460(6) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
N11 C37 1.166(8) . ?
C37 C38 1.455(10) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O11A 0.83(3) 1.92(4) 2.616(4) 140(5) 2_755 yes
O1 H1 O11B 0.83(3) 2.11(4) 2.926(14) 165(5) 2_755 yes
O6 H6 N6 0.90(3) 1.81(4) 2.578(4) 142(5) . yes
N1 H1A O1 0.75(3) 2.09(4) 2.598(4) 125(4) . yes
N3 H3 O3 0.81(3) 2.30(3) 2.844(3) 125(3) . yes
N3 H3 O4 0.81(3) 2.26(3) 2.848(4) 129(3) . yes
N4 H4 O13 0.88(3) 1.89(3) 2.774(5) 175(4) . yes
O16 H16C O2 0.87(4) 2.50(10) 3.221(9) 141(12) . yes
O16 H16D O5 0.88(4) 2.15(9) 2.914(8) 146(13) . yes
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
Br1 C13 C14 C9 -178.8(2) . . . . ?
Br2 C25 C26 C21 -179.8(3) . . . . ?
Cu1 O2 C7 N1 2.5(4) . . . . ?
Cu1 O2 C7 C6 -176.4(2) . . . . ?
Cu1 O3 C10 C9 -3.9(4) . . . . ?
Cu1 O3 C10 C11 176.5(2) . . . . ?
Cu1 O7 N7 O8 -5.9(4) . . . . ?
Cu1 O7 N7 O9 174.2(3) . . . . ?
Cu1 O10A N8 O11A -9.5(4) . . . . ?
Cu1 O10A N8 O12A 164.6(4) . . . . ?
Cu1 O11B N8 O10B 0(2) . . . . ?
Cu1 O11B N8 O12B 176.3(17) . . . . ?
Cu1 N2 C8 C9 2.3(5) . . . . ?
Cu2 O4 C22 C21 176.1(2) . . . . ?
Cu2 O4 C22 C23 -6.6(5) . . . . ?
Cu2 O5 C28 N6 -1.9(4) . . . . ?
Cu2 O5 C28 C29 176.7(2) . . . . ?
Cu2 O7 N7 O8 -176.8(3) . . . . ?
Cu2 O7 N7 O9 3.2(4) . . . . ?
Cu2 O10A N8 O11A 129.3(4) . . . . ?
Cu2 O10A N8 O12A -56.6(6) . . . . ?
Cu2 O10B N8 O11B -4(2) . . . . ?
Cu2 O10B N8 O12B 178.5(17) . . . . ?
Cu2 N5 N6 C28 1.0(3) . . . . ?
Cu2 N5 C27 C23 -3.1(5) . . . . ?
O1 C1 C2 C3 -178.8(4) . . . . ?
O1 C1 C6 C5 -178.8(3) . . . . ?
O1 C1 C6 C7 4.4(5) . . . . ?
O3 C10 C11 C12 -178.0(3) . . . . ?
O3 C10 C11 C15 2.7(4) . . . . ?
O4 C22 C23 C24 -176.0(3) . . . . ?
O4 C22 C23 C27 6.0(5) . . . . ?
O5 C28 C29 C30 -179.1(3) . . . . ?
O5 C28 C29 C34 1.7(5) . . . . ?
O6 C30 C31 C32 -177.7(4) . . . . ?
O7 Cu1 O3 C10 -178.5(2) . . . . ?
O7 Cu2 O4 C22 -176.6(3) . . . . ?
O10A Cu1 O3 C10 -105.4(3) . . . . ?
O10A Cu2 O4 C22 116.2(3) . . . . ?
O10B Cu2 O4 C22 91.5(4) . . . . ?
O11B Cu1 O3 C10 -70.4(4) . . . . ?
N1 N2 C8 C9 -179.1(3) . . . . ?
N2 Cu1 O3 C10 6.9(3) . . . . ?
N2 N1 C7 O2 -0.8(5) . . . . ?
N2 N1 C7 C6 178.0(3) . . . . ?
N2 C8 C9 C10 3.3(5) . . . . ?
N2 C8 C9 C14 -177.7(3) . . . . ?
N3 C16 C17 N4 166.5(3) . . . . ?
N3 C20 C21 C22 64.6(4) . . . . ?
N3 C20 C21 C26 -116.0(3) . . . . ?
N5 Cu2 O4 C22 2.6(3) . . . . ?
N5 N6 C28 O5 0.6(5) . . . . ?
N5 N6 C28 C29 -178.0(3) . . . . ?
N6 N5 C27 C23 179.0(3) . . . . ?
N6 C28 C29 C30 -0.5(5) . . . . ?
N6 C28 C29 C34 -179.7(3) . . . . ?
C1 C2 C3 C4 -2.9(6) . . . . ?
C1 C6 C7 O2 178.0(3) . . . . ?
C1 C6 C7 N1 -0.9(5) . . . . ?
C2 C1 C6 C5 1.4(5) . . . . ?
C2 C1 C6 C7 -175.4(3) . . . . ?
C2 C3 C4 C5 2.4(6) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C4 C5 C6 C1 -1.9(6) . . . . ?
C4 C5 C6 C7 175.0(3) . . . . ?
C5 C6 C7 O2 1.2(5) . . . . ?
C5 C6 C7 N1 -177.7(3) . . . . ?
C6 C1 C2 C3 0.9(6) . . . . ?
C7 N1 N2 Cu1 -1.3(3) . . . . ?
C7 N1 N2 C8 179.9(3) . . . . ?
C8 C9 C10 O3 -2.5(5) . . . . ?
C8 C9 C10 C11 177.1(3) . . . . ?
C8 C9 C14 C13 -178.6(3) . . . . ?
C9 C10 C11 C12 2.4(4) . . . . ?
C9 C10 C11 C15 -176.9(3) . . . . ?
C10 C9 C14 C13 0.4(5) . . . . ?
C10 C11 C12 C13 -1.3(5) . . . . ?
C10 C11 C15 N3 -62.2(4) . . . . ?
C11 C12 C13 Br1 179.2(2) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C12 C11 C15 N3 118.6(3) . . . . ?
C12 C13 C14 C9 0.8(5) . . . . ?
C14 C9 C10 O3 178.5(3) . . . . ?
C14 C9 C10 C11 -1.9(4) . . . . ?
C15 N3 C16 C17 130.6(3) . . . . ?
C15 N3 C20 C21 179.2(3) . . . . ?
C15 C11 C12 C13 177.9(3) . . . . ?
C16 N3 C15 C11 -58.6(3) . . . . ?
C16 N3 C20 C21 53.4(4) . . . . ?
C18 N4 C17 C16 163.3(3) . . . . ?
C19 N4 C17 C16 -71.9(4) . . . . ?
C20 N3 C15 C11 175.6(3) . . . . ?
C20 N3 C16 C17 -104.4(3) . . . . ?
C20 C21 C22 O4 -4.5(4) . . . . ?
C20 C21 C22 C23 177.9(3) . . . . ?
C20 C21 C26 C25 -178.9(3) . . . . ?
C21 C22 C23 C24 1.4(5) . . . . ?
C21 C22 C23 C27 -176.7(3) . . . . ?
C22 C21 C26 C25 0.5(5) . . . . ?
C22 C23 C24 C25 -0.3(5) . . . . ?
C22 C23 C27 N5 -0.8(5) . . . . ?
C23 C24 C25 Br2 179.7(3) . . . . ?
C23 C24 C25 C26 -0.8(6) . . . . ?
C24 C23 C27 N5 -178.9(3) . . . . ?
C24 C25 C26 C21 0.7(5) . . . . ?
C26 C21 C22 O4 176.0(3) . . . . ?
C26 C21 C22 C23 -1.5(5) . . . . ?
C27 N5 N6 C28 179.2(3) . . . . ?
C27 C23 C24 C25 177.9(3) . . . . ?
C28 C29 C30 O6 -1.8(5) . . . . ?
C28 C29 C30 C31 179.9(3) . . . . ?
C28 C29 C34 C33 179.5(4) . . . . ?
C29 C30 C31 C32 0.7(6) . . . . ?
C30 C29 C34 C33 0.3(6) . . . . ?
C30 C31 C32 C33 0.1(6) . . . . ?
C31 C32 C33 C34 -0.7(6) . . . . ?
C32 C33 C34 C29 0.5(6) . . . . ?
C34 C29 C30 O6 177.4(3) . . . . ?
C34 C29 C30 C31 -0.9(5) . . . . ?
