Reductive Elimination at Carbon under Steric Control.
Tolentino, Daniel R.; Neale, Samuel E.; Isaac, Connie J.; Macgregor, Stuart A.; Whittlesey, Michael K.; Jazzar, Rodolphe; Bertrand, Guy; Journal of the American Chemical Society 141 (2019) 9823–9826; doi:10.1021/jacs.9b04957

data_4128285
_publ_section_title
;
 Reductive Elimination at Carbon under Steric Control.
;
_journal_issue                   25
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9823
_journal_page_last               9826
_journal_paper_doi               10.1021/jacs.9b04957
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C39 H54 N P'
_chemical_formula_sum            'C39 H54 N P'
_chemical_formula_weight         567.80
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-12
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_cell_angle_alpha                90
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_cell_length_b                   18.8888(4)
_cell_length_c                   19.5947(5)
_cell_measurement_reflns_used    7720
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.43
_cell_measurement_theta_min      3.27
_cell_volume                     6797.6(3)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            45963
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.322
_diffrn_reflns_theta_min         3.250
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.894
_exptl_absorpt_correction_T_max  0.3201
_exptl_absorpt_correction_T_min  0.2252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0672 before and 0.0588 after correction. The Ratio of minimum to maximum transmission is 0.7035. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_description       block
_exptl_crystal_F_000             2480
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 4450 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     757
_refine_ls_number_reflns         12442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0791P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1188
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                10908
_reflns_number_total             12442
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            2PH_MenthCAACPh2PH.cif
_cod_data_source_block           2ph_menthcaacph2ph
_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/current/ACS/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               4128285
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.821
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C13(H13), C16(H16), C20(H20), C23(H23), C24(H24), C40(H40), C52(H52),
 C55(H55), C60(H60), C63(H63), C65(H65)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B), C42(H42A,H42B),
 C59(H59A,H59B), C61(H61A,H61B), C62(H62A,H62B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33),
 C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C48(H48), C49(H49), C50(H50),
  C69(H69), C70(H70), C71(H71), C72(H72), C73(H73), C75(H75), C76(H76),
 C77(H77), C78(H78), C79(H79)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C),
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C53(H53A,
 H53B,H53C), C54(H54A,H54B,H54C), C56(H56A,H56B,H56C), C57(H57A,H57B,H57C),
 C64(H64A,H64B,H64C), C66(H66A,H66B,H66C), C67(H67A,H67B,H67C)
;
_shelx_res_checksum              76412
_shelx_hkl_checksum              45160
_olex2_submission_special_instructions 'No special instructions were received'