#------------------------------------------------------------------------------
#$Date: 2019-11-04 15:20:04 +0200 (Mon, 04 Nov 2019) $
#$Revision: 223131 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/46/4034654.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_4034654
loop_
_publ_author_name
'Kumar, Manoj'
'Verma, Shalini'
'Mishra, Pawan K.'
'Verma, Akhilesh K.'
_publ_section_title
;
 Cu(II)-Mediated Ortho-C-H Amination of Arenes with Free Amines.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8067
_journal_page_last               8079
_journal_paper_doi               10.1021/acs.joc.9b00931
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C17 H19 N3 O3'
_chemical_formula_weight         313.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0333(3)
_cell_length_b                   6.8004(2)
_cell_length_c                   17.1688(4)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.687
_cell_measurement_theta_min      2.373
_cell_volume                     1521.70(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14037
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.687
_diffrn_reflns_theta_min         2.373
_exptl_absorpt_coefficient_mu    0.096
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       Needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         1568
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0377
_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/[σ²(Fo²)+(0.0462P)²+0.5742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0965
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1415
_reflns_number_total             1568
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b00931_si_004.cif
_cod_data_source_block           AV-MD-225
_cod_database_code               4034654
_shelx_shelxl_version_number     2016/4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O3 O 0.07200(9) 0.250000 0.50033(8) 0.0275(3) Uani 1 2 d S T P
O1 O 0.59769(9) 0.250000 0.48081(7) 0.0276(3) Uani 1 2 d S T P
N3 N 0.28168(10) 0.250000 0.54788(8) 0.0186(3) Uani 1 2 d S T P
N1 N 0.43338(10) 0.250000 0.43716(8) 0.0179(3) Uani 1 2 d S T P
H1 H 0.370176 0.250000 0.451556 0.022 Uiso 1 2 calc R U P
O2 O 0.27547(9) 0.250000 0.34944(8) 0.0452(5) Uani 1 2 d S T P
N2 N 0.36474(11) 0.250000 0.31430(8) 0.0268(4) Uani 1 2 d S T P
C7 C 0.36606(13) 0.250000 0.60289(9) 0.0187(4) Uani 1 2 d S T P
C8 C 0.45239(12) 0.250000 0.35799(10) 0.0182(4) Uani 1 2 d S T P
C2 C 0.46822(12) 0.250000 0.57730(9) 0.0175(4) Uani 1 2 d S T P
C1 C 0.50577(13) 0.250000 0.49461(9) 0.0176(4) Uani 1 2 d S T P
C9 C 0.54630(13) 0.250000 0.32018(10) 0.0218(4) Uani 1 2 d S T P
H9 H 0.606520 0.250000 0.349235 0.026 Uiso 1 2 calc R U P
C3 C 0.54573(13) 0.250000 0.63382(10) 0.0226(4) Uani 1 2 d S T P
H3 H 0.613989 0.250000 0.618031 0.027 Uiso 1 2 calc R U P
C6 C 0.34567(14) 0.250000 0.68235(10) 0.0245(4) Uani 1 2 d S T P
H6 H 0.277677 0.250000 0.698784 0.029 Uiso 1 2 calc R U P
C13 C 0.21691(9) 0.42667(19) 0.55518(7) 0.0235(3) Uani 1 1 d . . .
H13B H 0.258582 0.543839 0.549071 0.028 Uiso 1 1 calc R U .
H13A H 0.185452 0.430281 0.606358 0.028 Uiso 1 1 calc R U .
C5 C 0.42271(15) 0.250000 0.73817(10) 0.0266(4) Uani 1 2 d S T P
C14 C 0.13472(9) 0.4215(2) 0.49311(7) 0.0266(3) Uani 1 1 d . . .
H14B H 0.092109 0.537921 0.497524 0.032 Uiso 1 1 calc R U .
H14A H 0.166708 0.422845 0.442098 0.032 Uiso 1 1 calc R U .
C11 C 0.46168(15) 0.250000 0.19716(11) 0.0288(4) Uani 1 2 d S T P
H11 H 0.463800 0.250000 0.143021 0.035 Uiso 1 2 calc R U P
C4 C 0.52328(15) 0.250000 0.71228(10) 0.0267(4) Uani 1 2 d S T P
H4 H 0.576501 0.250000 0.748358 0.032 Uiso 1 2 calc R U P
C10 C 0.55148(14) 0.250000 0.24004(11) 0.0260(4) Uani 1 2 d S T P
H10 H 0.614766 0.250000 0.215015 0.031 Uiso 1 2 calc R U P
C12 C 0.36973(15) 0.250000 0.23547(10) 0.0324(5) Uani 1 2 d S T P
H12 H 0.309212 0.250000 0.206763 0.039 Uiso 1 2 calc R U P
C15 C 0.39592(19) 0.250000 0.82311(11) 0.0415(6) Uani 1 2 d S T P
H15A H 0.453956 0.206099 0.852825 0.062 Uiso 0.5 1 calc R U P
H15C H 0.339029 0.163138 0.831937 0.062 Uiso 0.5 1 calc R U P
H15B H 0.377613 0.380763 0.838950 0.062 Uiso 0.5 1 calc R U P
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 0.0000 0.0000 '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 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C14 O3 C14 109.34(13) . 7_565
C7 N3 C13 112.29(8) . 7_565
C7 N3 C13 112.29(8) . .
C13 N3 C13 109.22(13) 7_565 .
C1 N1 C8 125.94(14) . .
C1 N1 H1 117.0 . .
C8 N1 H1 117.0 . .
O2 N2 C12 120.16(15) . .
O2 N2 C8 119.31(14) . .
C12 N2 C8 120.54(15) . .
C6 C7 C2 119.28(16) . .
C6 C7 N3 119.63(15) . .
C2 C7 N3 121.09(14) . .
N2 C8 N1 112.96(14) . .
N2 C8 C9 118.77(15) . .
N1 C8 C9 128.27(15) . .
C3 C2 C7 117.89(15) . .
C3 C2 C1 114.83(15) . .
C7 C2 C1 127.28(15) . .
O1 C1 N1 122.55(15) . .
O1 C1 C2 120.20(15) . .
N1 C1 C2 117.25(14) . .
C10 C9 C8 120.75(16) . .
C10 C9 H9 119.6 . .
C8 C9 H9 119.6 . .
C4 C3 C2 121.59(17) . .
C4 C3 H3 119.2 . .
C2 C3 H3 119.2 . .
C5 C6 C7 122.64(17) . .
C5 C6 H6 118.7 . .
C7 C6 H6 118.7 . .
N3 C13 C14 109.10(11) . .
N3 C13 H13B 109.9 . .
C14 C13 H13B 109.9 . .
N3 C13 H13A 109.9 . .
C14 C13 H13A 109.9 . .
H13B C13 H13A 108.3 . .
C4 C5 C6 117.60(16) . .
C4 C5 C15 122.20(18) . .
C6 C5 C15 120.20(18) . .
O3 C14 C13 111.29(11) . .
O3 C14 H14B 109.4 . .
C13 C14 H14B 109.4 . .
O3 C14 H14A 109.4 . .
C13 C14 H14A 109.4 . .
H14B C14 H14A 108.0 . .
C12 C11 C10 119.08(17) . .
C12 C11 H11 120.5 . .
C10 C11 H11 120.5 . .
C3 C4 C5 120.99(17) . .
C3 C4 H4 119.5 . .
C5 C4 H4 119.5 . .
C9 C10 C11 119.35(16) . .
C9 C10 H10 120.3 . .
C11 C10 H10 120.3 . .
N2 C12 C11 121.50(17) . .
N2 C12 H12 119.2 . .
C11 C12 H12 119.2 . .
C5 C15 H15A 109.5 . .
C5 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
C5 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
H15C C15 H15B 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C14 1.4296(15) .
O3 C14 1.4296(15) 7_565
O1 C1 1.221(2) .
N3 C7 1.450(2) .
N3 C13 1.4737(14) 7_565
N3 C13 1.4737(14) .
N1 C1 1.365(2) .
N1 C8 1.382(2) .
N1 H1 0.8600 .
O2 N2 1.3106(19) .
N2 C12 1.355(2) .
N2 C8 1.367(2) .
C7 C6 1.390(2) .
C7 C2 1.402(2) .
C8 C9 1.385(2) .
C2 C3 1.401(2) .
C2 C1 1.502(2) .
C9 C10 1.378(3) .
C9 H9 0.9300 .
C3 C4 1.378(3) .
C3 H3 0.9300 .
C6 C5 1.388(2) .
C6 H6 0.9300 .
C13 C14 1.5114(17) .
C13 H13B 0.9700 .
C13 H13A 0.9700 .
C5 C4 1.384(3) .
C5 C15 1.500(3) .
C14 H14B 0.9700 .
C14 H14A 0.9700 .
C11 C12 1.367(3) .
C11 C10 1.383(3) .
C11 H11 0.9300 .
C4 H4 0.9300 .
C10 H10 0.9300 .
C12 H12 0.9300 .
C15 H15A 0.9600 .
C15 H15C 0.9600 .
C15 H15B 0.9600 .
