#------------------------------------------------------------------------------
#$Date: 2019-11-26 14:34:38 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243533 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/61/1556179.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1556179
loop_
_publ_author_name
'Parella, Ramarao'
'Gopalakrishnan, Bojan'
'Babu, Srinivasarao Arulananda'
_publ_section_title
;
 Auxiliary-enabled Pd-catalyzed direct arylation of methylene C(sp3)-H
 bond of cyclopropanes: highly diastereoselective assembling of di- and
 trisubstituted cyclopropanecarboxamides.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3238
_journal_page_last               3241
_journal_paper_doi               10.1021/ol4012212
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C20 H18 N2 O2'
_chemical_formula_sum            'C20 H18 N2 O2'
_chemical_formula_weight         318.36
_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             2012-10-22T19:19:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 106.519(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.639(3)
_cell_length_b                   10.357(2)
_cell_length_c                   12.061(2)
_cell_measurement_temperature    296(2)
_cell_volume                     1633.4(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6403
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            ' colourless'
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0112(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0631P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.109
_refine_ls_wR_factor_ref         0.1204
_reflns_number_gt                1921
_reflns_number_total             2876
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4012212_si_002.cif
_cod_data_source_block           pr837b2
_cod_original_cell_volume        1633.5(5)
_cod_database_code               1556179
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.28352(10) 0.38872(13) 0.81352(13) 0.0837(4) Uani 1 1 d .
O2 O 0.68206(9) 0.36210(14) 0.69963(13) 0.0864(5) Uani 1 1 d .
N1 N 0.77737(10) 0.18026(14) 0.73980(12) 0.0616(4) Uani 1 1 d .
H1 H 0.7796 0.1013 0.7185 0.074 Uiso 1 1 calc R
N2 N 0.95139(10) 0.04636(15) 0.78860(12) 0.0625(4) Uani 1 1 d .
C1 C 0.22548(16) 0.3063(2) 0.8646(2) 0.0902(7) Uani 1 1 d .
H1A H 0.1766 0.2596 0.8052 0.135 Uiso 1 1 calc R
H1B H 0.1902 0.3571 0.9078 0.135 Uiso 1 1 calc R
H1C H 0.2703 0.2465 0.9155 0.135 Uiso 1 1 calc R
C2 C 0.34010(12) 0.33327(18) 0.74792(17) 0.0636(5) Uani 1 1 d .
C3 C 0.39231(13) 0.41865(18) 0.69763(18) 0.0697(5) Uani 1 1 d .
H3 H 0.3874 0.507 0.709 0.084 Uiso 1 1 calc R
C4 C 0.45139(13) 0.37395(18) 0.63098(18) 0.0687(5) Uani 1 1 d .
H4 H 0.4865 0.4329 0.5984 0.082 Uiso 1 1 calc R
C5 C 0.46031(12) 0.24287(18) 0.61076(15) 0.0624(5) Uani 1 1 d .
C6 C 0.52006(14) 0.19012(19) 0.53583(17) 0.0716(6) Uani 1 1 d .
H6 H 0.4883 0.1131 0.4933 0.086 Uiso 1 1 calc R
C7 C 0.63713(14) 0.18497(18) 0.56873(16) 0.0690(5) Uani 1 1 d .
H7 H 0.6669 0.1062 0.547 0.083 Uiso 1 1 calc R
C8 C 0.69911(13) 0.25198(19) 0.67443(16) 0.0622(5) Uani 1 1 d .
C9 C 0.85512(12) 0.21830(17) 0.83766(14) 0.0558(4) Uani 1 1 d .
C10 C 0.94679(12) 0.14396(17) 0.86201(14) 0.0549(4) Uani 1 1 d .
C11 C 1.02844(13) 0.1741(2) 0.96084(16) 0.0669(5) Uani 1 1 d .
C12 C 1.11604(15) 0.0961(3) 0.9816(2) 0.0836(7) Uani 1 1 d .
H12 H 1.1711 0.1109 1.0465 0.1 Uiso 1 1 calc R
C13 C 1.12076(15) 0.0003(3) 0.9081(2) 0.0884(7) Uani 1 1 d .
H13 H 1.179 -0.0508 0.921 0.106 Uiso 1 1 calc R
C14 C 0.57627(15) 0.2666(2) 0.47117(17) 0.0838(6) Uani 1 1 d .
H14A H 0.5787 0.3594 0.4823 0.101 Uiso 1 1 calc R
H14B H 0.5723 0.239 0.3932 0.101 Uiso 1 1 calc R
C15 C 0.84745(15) 0.31853(19) 0.90925(17) 0.0703(5) Uani 1 1 d .
H15 H 0.7877 0.3671 0.8938 0.084 Uiso 1 1 calc R
C16 C 0.92987(19) 0.3473(2) 1.00545(18) 0.0843(6) Uani 1 1 d .
H16 H 0.9242 0.4161 1.0529 0.101 Uiso 1 1 calc R
C17 C 1.01724(19) 0.2783(2) 1.03136(18) 0.0845(6) Uani 1 1 d .
H17 H 1.0705 0.2996 1.0962 0.101 Uiso 1 1 calc R
C18 C 1.03663(15) -0.0209(2) 0.81219(18) 0.0777(6) Uani 1 1 d .
H18 H 1.0412 -0.087 0.7617 0.093 Uiso 1 1 calc R
C19 C 0.40697(14) 0.15972(18) 0.66310(18) 0.0710(6) Uani 1 1 d .
H19 H 0.4118 0.0713 0.6522 0.085 Uiso 1 1 calc R
C20 C 0.34716(14) 0.20281(18) 0.73062(17) 0.0696(6) Uani 1 1 d .
H20 H 0.3121 0.1444 0.7639 0.083 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 O1 C1 118.13(16)
C8 N1 C9 128.24(15)
C8 N1 H1 115.9
C9 N1 H1 115.9
C18 N2 C10 117.10(16)
O1 C1 H1A 109.5
O1 C1 H1B 109.5
H1A C1 H1B 109.5
O1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C20 C2 O1 124.87(18)
C20 C2 C3 119.7(2)
O1 C2 C3 115.39(17)
C4 C3 C2 120.30(18)
C4 C3 H3 119.8
C2 C3 H3 119.9
C3 C4 C5 121.86(18)
C3 C4 H4 119.1
C5 C4 H4 119.1
C19 C5 C4 116.24(19)
C19 C5 C6 119.88(18)
C4 C5 C6 123.86(18)
C14 C6 C5 125.78(18)
C14 C6 C7 59.63(13)
C5 C6 C7 124.59(15)
C14 C6 H6 112.4
C5 C6 H6 112.4
C7 C6 H6 112.4
C8 C7 C14 117.67(17)
C8 C7 C6 120.16(16)
C14 C7 C6 58.12(12)
C8 C7 H7 116.1
C14 C7 H7 116.1
C6 C7 H7 116.1
O2 C8 N1 122.84(17)
O2 C8 C7 123.25(16)
N1 C8 C7 113.90(16)
C15 C9 N1 124.60(16)
C15 C9 C10 119.85(16)
N1 C9 C10 115.54(15)
N2 C10 C11 122.85(16)
N2 C10 C9 117.93(14)
C11 C10 C9 119.22(17)
C12 C11 C17 124.4(2)
C12 C11 C10 116.7(2)
C17 C11 C10 118.87(19)
C13 C12 C11 120.3(2)
C13 C12 H12 119.8
C11 C12 H12 119.8
C12 C13 C18 118.7(2)
C12 C13 H13 120.6
C18 C13 H13 120.6
C6 C14 C7 62.25(13)
C6 C14 H14A 117.5
C7 C14 H14A 117.5
C6 C14 H14B 117.5
C7 C14 H14B 117.5
H14A C14 H14B 114.6
C9 C15 C16 119.73(19)
C9 C15 H15 120.1
C16 C15 H15 120.1
C17 C16 C15 121.9(2)
C17 C16 H16 119.1
C15 C16 H16 119.1
C16 C17 C11 120.44(19)
C16 C17 H17 119.8
C11 C17 H17 119.8
N2 C18 C13 124.3(2)
N2 C18 H18 117.9
C13 C18 H18 117.9
C20 C19 C5 122.77(18)
C20 C19 H19 118.6
C5 C19 H19 118.6
C2 C20 C19 119.07(18)
C2 C20 H20 120.5
C19 C20 H20 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.378(2)
O1 C1 1.419(2)
O2 C8 1.220(2)
N1 C8 1.354(2)
N1 C9 1.400(2)
N1 H1 0.86
N2 C18 1.315(2)
N2 C10 1.357(2)
C1 H1A 0.96
C1 H1B 0.96
C1 H1C 0.96
C2 C20 1.375(3)
C2 C3 1.379(3)
C3 C4 1.370(3)
C3 H3 0.93
C4 C5 1.391(3)
C4 H4 0.93
C5 C19 1.389(3)
C5 C6 1.483(3)
C6 C14 1.471(3)
C6 C7 1.533(3)
C6 H6 0.98
C7 C8 1.486(3)
C7 C14 1.494(2)
C7 H7 0.98
C9 C15 1.373(2)
C9 C10 1.426(2)
C10 C11 1.416(2)
C11 C12 1.404(3)
C11 C17 1.409(3)
C12 C13 1.344(3)
C12 H12 0.93
C13 C18 1.396(3)
C13 H13 0.93
C14 H14A 0.97
C14 H14B 0.97
C15 C16 1.399(3)
C15 H15 0.93
C16 C17 1.348(3)
C16 H16 0.93
C17 H17 0.93
C18 H18 0.93
C19 C20 1.380(3)
C19 H19 0.93
C20 H20 0.93
