Contributions of inner and outer coordination sphere bonding in determining the strength of substituted phenolic pyrazoles as copper extractants.
Healy, Mary R.; Roebuck, James W.; Doidge, Euan D.; Emeleus, Lucy C.; Bailey, Philip J.; Campbell, John; Fischmann, Adam J.; Love, Jason B.; Morrison, Carole A.; Sassi, Thomas; White, David J.; Tasker, Peter A.; Dalton transactions (Cambridge, England : 2003) 45 (2016) 3055–3062; doi:10.1039/c5dt04055h

data_7037997
_publ_section_title
;
 Contributions of inner and outer coordination sphere bonding in
 determining the strength of substituted phenolic pyrazoles as copper
 extractants.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3055
_journal_page_last               3062
_journal_paper_doi               10.1039/c5dt04055h
_journal_volume                  45
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C9 H7 Br1 N2 O1'
_chemical_formula_sum            'C9 H7 Br N2 O'
_chemical_formula_weight         239.07
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2015-11-03 deposited with the CCDC.
2015-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.84135(10)
_cell_length_b                   9.9290(2)
_cell_length_c                   22.7560(6)
_cell_measurement_reflns_used    8254
_cell_measurement_temperature    137
_cell_measurement_theta_max      76
_cell_measurement_theta_min      4
_cell_volume                     867.93(4)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      137
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15277
_diffrn_reflns_theta_full        76.214
_diffrn_reflns_theta_max         76.214
_diffrn_reflns_theta_min         3.885
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.113
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.41
_refine_ls_abs_structure_details 'Flack (1983), 696 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0189
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1807
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0198
_refine_ls_R_factor_gt           0.0192
_refine_ls_shift/su_max          0.0004730
_refine_ls_shift/su_mean         0.0000221
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 0.71P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0465
_refine_ls_wR_factor_gt          0.0463
_refine_ls_wR_factor_ref         0.0465
_reflns_limit_h_max              4
_reflns_limit_h_min              -4
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                1776
_reflns_number_total             1812
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0198
_oxford_refine_ls_scale          6.28(9)
_oxford_reflns_number_all        1807
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            c5dt04055h2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7037996--7037997.cif.'
_cod_original_cell_volume        867.94(4)
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C9 H7 Br1 N2 O1'
_cod_database_code               7037997
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT BR   (    1 ,X'S,U'S)  UNTIL C    (  111 ) 
CONT H    (  911 ,X'S)  UNTIL H    (  111 ) 
CONT ENANTIO 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) 
RIDE C   ( 101,X'S) H   (1011,X'S) 
RIDE C   ( 111,X'S) H   (1111,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM       H ON O-HETRO ATOM 
DIST 0.82, 0.02 = 
CONT O ( 11) TO H(111) 
REST 0.040, 0.002 = H(111,U[ISO]) 
REM            H1-N-R2 
DIST 0.86, 0.02 = 
CONT N ( 91) TO H(911) 
REST 0.033, 0.002 = H(911,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(911) TO N ( 91) TO N(81) 
CONT H(911) TO N ( 91) TO C(101) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;