Diastereoselective Pd(II)-Catalyzed sp<sup>3</sup> C-H Arylation Followed by Ring Opening of Cyclopropanecarboxamides: Construction of anti β-Acyloxy Carboxamide Derivatives.
Gopalakrishnan, Bojan; Mohan, Sruthi; Parella, Ramarao; Babu, Srinivasarao Arulananda; The Journal of organic chemistry 81 (2016) 8988–9005; doi:10.1021/acs.joc.6b01635

data_4037165
_publ_section_title
;
 Diastereoselective Pd(II)-Catalyzed sp<sup>3</sup> C-H Arylation Followed
 by Ring Opening of Cyclopropanecarboxamides: Construction of anti
 \b-Acyloxy Carboxamide Derivatives.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8988
_journal_page_last               9005
_journal_paper_doi               10.1021/acs.joc.6b01635
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C36 H34 N2 O3'
_chemical_formula_sum            'C36 H34 N2 O3'
_chemical_formula_weight         542.65
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-21
_audit_creation_method
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Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
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_cell_angle_alpha                89.790(9)
_cell_angle_beta                 85.921(7)
_cell_angle_gamma                78.734(8)
_cell_formula_units_Z            2
_cell_length_a                   8.8959(5)
_cell_length_b                   11.9585(7)
_cell_length_c                   13.9954(13)
_cell_measurement_reflns_used    3059
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     1456.39(18)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
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CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
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_computing_data_reduction
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CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 50.0000
	          2theta: 29.9000
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 50.0000
	          2theta: 29.9000
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 50.0000
	          2theta: 29.9000
;
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
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_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.107305
_diffrn_orient_matrix_UB_12      -0.024041
_diffrn_orient_matrix_UB_13      0.033370
_diffrn_orient_matrix_UB_21      -0.008615
_diffrn_orient_matrix_UB_22      0.080332
_diffrn_orient_matrix_UB_23      -0.027267
_diffrn_orient_matrix_UB_31      -0.010179
_diffrn_orient_matrix_UB_32      -0.023057
_diffrn_orient_matrix_UB_33      -0.067057
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12889
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         3.078
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0811P)^2^+0.1272P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1733
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3932
_reflns_number_total             5120
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01635_si_004.cif
_cod_data_source_block           shelx
_cod_database_code               4037165
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C19(H19), C20(H20),
 C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29), C31(H31), C32(H32),
  C34(H34), C35(H35), C36(H36)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C17(H17A,H17B,H17C), C22(H22A,H22B,H22C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              54732
_shelx_hkl_checksum              89169
_olex2_submission_special_instructions 'No special instructions were received'