Palladium-Catalyzed Ortho-Arylation of Carbamate-Protected Estrogens.
Bedford, Robin B.; Brenner, Peter B.; Durrant, Steven J.; Gallagher, Timothy; Méndez-Gálvez, Carolina; Montgomery, Michelle; The Journal of organic chemistry 81 (2016) 3473–3478; doi:10.1021/acs.joc.6b00532

data_4036795
_publ_section_title
;
 Palladium-Catalyzed Ortho-Arylation of Carbamate-Protected Estrogens.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3473
_journal_page_last               3478
_journal_paper_doi               10.1021/acs.joc.6b00532
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C29 H34 Br N O3'
_chemical_formula_sum            'C29 H34 Br N O3'
_chemical_formula_weight         524.50
_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_Int_Tables_number      19
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-10
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8209(1)
_cell_length_b                   17.0464(3)
_cell_length_c                   21.4158(4)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.87
_cell_measurement_theta_min      2.25
_cell_volume                     2490.05(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.02
_diffrn_measured_fraction_theta_full 0.9996
_diffrn_measured_fraction_theta_max 0.9988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            44333
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         27.61
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    1.682
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0669 before and 0.0571 after correction.
The Ratio of minimum to maximum transmission is 0.8777.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3990
_exptl_crystal_description       block
_exptl_crystal_F_000             1095.3286
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.3617
_refine_diff_density_min         -0.2436
_refine_diff_density_rms         0.0596
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.023(6)
_refine_ls_d_res_high            0.7667
_refine_ls_d_res_low             9.0674
_refine_ls_goodness_of_fit_ref   1.0345
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    54
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0345
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0268
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+0.1953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0635
_reflns_Friedel_coverage         0.998
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              22
_reflns_limit_k_min              -22
_reflns_limit_l_max              27
_reflns_limit_l_min              -27
_reflns_number_gt                5319
_reflns_number_total             5772
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo6b00532_si_001.cif
_cod_data_source_block           test
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               4036795
_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:
 C22(H22), C23(H23), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19a,H19b), C16(H16a,H16b), C20(H20a,H20b), C26(H26a,H26b), C28(H28a,
 H28b), C32(H32a,H32b), C30(H30a,H30b), C31(H31a,H31b)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C9(H9), C3(H3), C12(H12), C6(H6)
2.d Idealised Me refined as rotating group:
 C34(H34a,H34b,H34c), C27(H27a,H27b,H27c), C24(H24a,H24b,H24c)
;
_olex2_submission_special_instructions 'No special instructions were received'