Employing carboxylic acids in aryne multicomponent coupling triggered by aziridines/azetidines
Roy, Tony; Bhojgude, Sachin Suresh; Kaicharla, Trinadh; Thangaraj, Manikandan; Garai, Bikash; Biju, Akkattu T.; Organic Chemistry Frontiers 3 (2016) 71–; doi:10.1039/C5QO00328H

data_1553203
_publ_section_title
;
 Employing carboxylic acids in aryne multicomponent coupling triggered by
 aziridines/azetidines
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              71
_journal_paper_doi               10.1039/C5QO00328H
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C27 H29 N O2'
_chemical_formula_sum            'C27 H29 N O2'
_chemical_formula_weight         399.51
_chemical_name_common            TNY-TE-09
_chemical_name_systematic
;
Benzoic acid 2-(cyclohexyl-phenyl-amino)-1-phenyl-ethyl ester
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-02-17
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled Nov  7 2012 10:34:12, GUI svn.r4372)
;
_audit_update_record
;
2015-02-18 deposited with the CCDC.
2015-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.399(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.5737(5)
_cell_length_b                   12.7774(4)
_cell_length_c                   11.4615(3)
_cell_measurement_temperature    298
_cell_volume                     2280.06(12)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.875
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10221
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.01
_diffrn_reflns_theta_min         3.19
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0678
_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^)+(0.0770P)^2^+0.6751P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1884
_refine_ls_wR_factor_ref         0.2219
_reflns_number_gt                2970
_reflns_number_total             5313
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00328h2.cif
_cod_data_source_block           TNY-TE-09
_cod_original_cell_volume        2280.08(12)
_cod_database_code               1553203
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H22 of C22, {H15a,H15b} of C15, {H27a,H27b} of C27, H8 of C8, H20 of C20,
  {H24a,H24b} of C24, H21 of C21, H17 of C17, H2 of C2, H11 of C11, {H26a,H26b}
  of C26, H5 of C5, {H23a,H23b} of C23, H14 of C14, H6 of C6, H10 of C10, H3 of
  C3, H4 of C4, H12 of C12, H18 of C18, H19 of C19, H13 of C13, {H25a,H25b} of
  C25
2.a Ternary CH refined with riding coordinates:
 C8(H8), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b), C27(H27a,H27b), C23(H23a,H23b), C26(H26a,H26b), C24(H24a,
 H24b), C25(H25a,H25b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C17(H17), C21(H21), C14(H14), C2(H2), C10(H10), C5(H5), C11(H11),
 C20(H20), C12(H12), C13(H13), C18(H18), C3(H3), C4(H4), C19(H19)
;