A multifunctional use of bis(methylene)bis(5-bromo-2-hydroxyl salicyloylhydrazone): from metal sensing to ambient catalysis of A3 coupling reactions
Peewasan, Krisana; Merkel, Marcel P.; Fuhr, Olaf; Anson, Christopher E.; Powell, Annie K.; RSC Advances 10 (2020) 40739–40744; doi:10.1039/D0RA07687B

data_7241696
_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, \w 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(\m~2~-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/[\s^2^(Fo^2^)+(0.0653P)^2^+0.2616P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            d0ra07687b2.cif
_cod_data_source_block           kp439-re
_cod_database_code               7241696
_shelx_shelxl_version_number     2018/3
_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)
;
_shelx_res_checksum              53926
_olex2_submission_special_instructions 'No special instructions were received'