C−H Nickellation of Phenol-Derived Phosphinites: Regioselectivity and Structures of Cyclonickellated Complexes
Mangin, Loïc P; Zargarian, Davit; Dalton Transactions  (2017) –; doi:10.1039/C7DT03403B

data_7044641
_publ_section_title
;
 C&#x2212;H Nickellation of Phenol-Derived Phosphinites: Regioselectivity
 and Structures of Cyclonickellated Complexes
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/C7DT03403B
_journal_year                    2017
_chemical_formula_moiety         'C36 H44 Br2 Ni2 O2 P2'
_chemical_formula_sum            'C36 H44 Br2 Ni2 O2 P2'
_chemical_formula_weight         847.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-10-24 deposited with the CCDC.
2017-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.6650(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.6689(4)
_cell_length_b                   12.3775(3)
_cell_length_c                   36.7348(10)
_cell_measurement_reflns_used    9047
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.925
_cell_measurement_theta_min      4.308
_cell_volume                     7121.4(3)
_computing_cell_refinement
'SAINT (2013) V8.34A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
'SAINT (2013) V8.34A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_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    'XS (Sheldrick, 1986)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            149169
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.168
_diffrn_reflns_theta_min         1.203
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_exptl_absorpt_coefficient_mu    5.027
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1279 before and 0.0750 after correction. The Ratio of minimum to maximum transmission is 0.6766. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_description       block
_exptl_crystal_F_000             3456
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         2.166
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details
;
 Flack x determined using 10620 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1620
_refine_ls_number_reflns         26277
_refine_ls_number_restraints     1537
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0751P)^2^+18.5006P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1331
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                25715
_reflns_number_total             26277
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7dt03403b2.cif
_cod_data_source_block           loic64
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7044641
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.500
_shelx_estimated_absorpt_t_min   0.404
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.47(4)
 0.073(14) 0.35(3) 0.104(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16), C31(H31), C34(H34), C49(H49), C52(H52), C67(H67),
 C70(H70), C85(H85), C88(H88), C103(H103), C106(H106), C121(H121), C124(H124),
 C139(H139), C142(H142)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C21(H21), C22(H22), C23(H23), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30),
  C39(H39), C40(H40), C41(H41), C44(H44), C45(H45), C46(H46), C47(H47),
 C48(H48), C57(H57), C58(H58), C59(H59), C62(H62), C63(H63), C64(H64), C65(H65),
  C66(H66), C75(H75), C76(H76), C77(H77), C80(H80), C81(H81), C82(H82),
 C83(H83), C84(H84), C93(H93), C94(H94), C95(H95), C98(H98), C99(H99),
 C100(H100), C101(H101), C102(H102), C111(H111), C112(H112), C113(H113),
 C116(H116), C117(H117), C118(H118), C119(H119), C120(H120), C129(H129),
 C130(H130), C131(H131), C134(H134), C135(H135), C136(H136), C137(H137),
 C138(H138)
4.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C36(H36A,
 H36B,H36C), C50(H50A,H50B,H50C), C51(H51A,H51B,H51C), C53(H53A,H53B,H53C),
 C54(H54A,H54B,H54C), C68(H68A,H68B,H68C), C69(H69A,H69B,H69C), C71(H71A,H71B,
 H71C), C72(H72A,H72B,H72C), C86(H86A,H86B,H86C), C87(H87A,H87B,H87C), C89(H89A,
 H89B,H89C), C90(H90A,H90B,H90C), C104(H10A,H10B,H10C), C105(H10D,H10E,H10F),
 C107(H10G,H10H,H10I), C108(H10J,H10K,H10L), C122(H12A,H12B,H12C), C123(H12D,
 H12E,H12F), C125(H12G,H12H,H12I), C126(H12J,H12K,H12L), C140(H14D,H14E,H14F),
 C141(H14G,H14H,H14I), C143(H14J,H14K,H14L), C144(H14M,H14N,H14O)
;
_shelx_res_checksum              30305
_olex2_submission_special_instructions 'No special instructions were received'