Syntheses, Crystal Structures, and Properties of Four Metal–Organic Complexes Based on 1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic Acid
Yang, Jie; Liu, Xiaobin; Wang, Xiaoqing; Dai, Fangna; Zhou, Yan; Dong, Bin; Zhang, Liangliang; Liu, Yanru; Sun, Daofeng; Crystal Growth & Design 15 (2015) 4198–; doi:10.1021/acs.cgd.5b00164

data_4513533
_publ_section_title
;
 Syntheses, Crystal Structures, and Properties of Four Metal--Organic
 Complexes Based on
 1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic Acid
;
_journal_issue                   9
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              4198
_journal_paper_doi               10.1021/acs.cgd.5b00164
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C33 H20 Cl6 N4 Ni O5, C9 H4 Cl6 O4, H2 O'
_chemical_formula_sum            'C42 H26 Cl12 N4 Ni O10'
_chemical_formula_weight         1230.78
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                95.897(3)
_cell_angle_beta                 99.860(3)
_cell_angle_gamma                104.902(4)
_cell_formula_units_Z            2
_cell_length_a                   12.1783(4)
_cell_length_b                   12.6524(6)
_cell_length_c                   16.6968(6)
_cell_measurement_reflns_used    5871
_cell_measurement_temperature    267.48(10)
_cell_measurement_theta_max      69.4530
_cell_measurement_theta_min      3.6570
_cell_volume                     2420.19(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      267.48(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -22.00   69.00   1.0000    2.6250
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -150.0000 91

  2 omega  -69.00   22.00   1.0000    2.6250
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   60.0000 91

  3 omega  -50.00   10.00   1.0000    2.6250
omega____ theta____ kappa____ phi______ frames
    -        0.0000  111.0000 -170.0000 60

  4 omega  -17.00   86.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000   60.0000 103

  5 omega   32.00  123.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -30.0000 91

  6 omega   23.00  110.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  150.0000 87

  7 omega   23.00  123.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -180.0000 100

  8 omega    5.00   76.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -150.0000 71

  9 omega   23.00   80.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000   60.0000 57

 10 omega  -17.00  108.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000   30.0000 125

 11 omega   79.00  160.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 81

 12 omega   44.00   70.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 26

 13 omega   42.00  142.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -120.0000 100

 14 omega   85.00  137.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  150.0000 52

 15 omega   37.00   96.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 59

 16 omega   41.00   92.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 51

 17 omega   68.00  169.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   30.0000 101

 18 omega   95.00  165.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   60.0000 70

 19 omega   47.00  115.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 68

 20 omega  122.00  148.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -150.0000 26

 21 omega  144.00  175.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -60.0000 31

 22 omega   39.00   86.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 47

 23 omega   35.00   74.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 39

 24 omega   76.00  114.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 38

 25 omega   37.00  105.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 68

 26 omega   48.00  131.00   1.0000   10.5050
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000    0.0000 83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0007565000
_diffrn_orient_matrix_UB_12      -0.0843205000
_diffrn_orient_matrix_UB_13      -0.0732078000
_diffrn_orient_matrix_UB_21      0.0000698000
_diffrn_orient_matrix_UB_22      -0.0885219000
_diffrn_orient_matrix_UB_23      0.0568281000
_diffrn_orient_matrix_UB_31      -0.1337589000
_diffrn_orient_matrix_UB_32      -0.0362754000
_diffrn_orient_matrix_UB_33      -0.0198744000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17232
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         1.68
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.125
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            mauve
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1236
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.410
_refine_diff_density_min         -1.094
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         8625
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0790P)^2^+2.2120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1713
_reflns_number_gt                6000
_reflns_number_total             8625
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00164_si_002.cif
_cod_data_source_block           yj-320-4
_cod_depositor_comments
'Adding full bibliography for 4513533--4513536.cif.'
_cod_original_cell_volume        2420.20(17)
_cod_database_code               4513533
_chemical_oxdiff_formula         'C H O N Cl Ni'
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O7-H7
 0.85 with sigma of 0.02
3.a Free rotating group:
 O2W(H2WA,H2WB)
3.b Rotating group:
 O1W(H1WA,H1WB)
3.c Ternary CH refined with riding coordinates:
 C6(H6), C36(H36), C35(H35), C2(H2)
3.d Aromatic/amide H refined with riding coordinates:
 C12(H12), C10(H10), C17(H17), C29(H29), C11(H11), C14(H14), C27(H27),
 C26(H26), C15(H15), C18(H18), C30(H30), C31(H31), C22(H22), C23(H23), C19(H19),
  C24(H24)
3.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'