#------------------------------------------------------------------------------
#$Date: 2019-11-26 06:01:54 +0200 (Tue, 26 Nov 2019) $
#$Revision: 242782 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/29/4132907.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_4132907
loop_
_publ_author_name
'Yang, Qi-Liang'
'Wang, Xiang-Yang'
'Lu, Jia-Yan'
'Zhang, Li-Pu'
'Fang, Ping'
'Mei, Tian-Sheng'
_publ_section_title
;
 Copper-Catalyzed Electrochemical C-H Amination of Arenes with Secondary
 Amines.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11487
_journal_page_last               11494
_journal_paper_doi               10.1021/jacs.8b07380
_journal_volume                  140
_journal_year                    2018
_chemical_formula_sum            'C19 H18 N4 O2'
_chemical_formula_weight         334.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 108.073(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0640(5)
_cell_length_b                   6.8437(3)
_cell_length_c                   11.2124(5)
_cell_measurement_reflns_used    3224
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.933
_cell_measurement_theta_min      4.519
_cell_volume                     807.10(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.973
_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  0.0194
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4371
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.738
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.030
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1682
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0368
_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)+(0.0435P)²+0.1902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0984
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1526
_reflns_number_total             1682
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b07380_si_006.cif
_cod_data_source_block           mo_d8v18369_0m
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4132907
_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. 
;
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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
O1 O 0.91959(12) 0.2500 0.93253(11) 0.0415(4) Uani 1 2 d S T P
O2 O 0.29947(11) 0.2500 0.49929(10) 0.0353(3) Uani 1 2 d S T P
N1 N 0.75081(15) 0.2500 0.23157(13) 0.0362(4) Uani 1 2 d S T P
N2 N 0.76613(12) 0.2500 0.67996(12) 0.0273(3) Uani 1 2 d S T P
N3 N 0.51368(12) 0.2500 0.60324(12) 0.0266(3) Uani 1 2 d S T P
H3 H 0.5667 0.2500 0.6802 0.032 Uiso 1 2 calc R U P
N4 N 0.47533(13) 0.2500 0.82261(13) 0.0342(4) Uani 1 2 d S T P
C1 C 0.87592(18) 0.2500 0.26498(17) 0.0393(4) Uani 1 2 d S T P
H1A H 0.9147 0.2500 0.2003 0.047 Uiso 1 2 calc R U P
C2 C 0.95567(18) 0.2500 0.38965(18) 0.0396(4) Uani 1 2 d S T P
H2 H 1.0455 0.2500 0.4079 0.048 Uiso 1 2 calc R U P
C3 C 0.90237(16) 0.2500 0.48447(16) 0.0343(4) Uani 1 2 d S T P
H3A H 0.9550 0.2500 0.5694 0.041 Uiso 1 2 calc R U P
C4 C 0.76846(15) 0.2500 0.45558(15) 0.0280(4) Uani 1 2 d S T P
C5 C 0.70376(15) 0.2500 0.54737(14) 0.0259(4) Uani 1 2 d S T P
C6 C 0.57194(14) 0.2500 0.50934(14) 0.0250(4) Uani 1 2 d S T P
C7 C 0.50139(16) 0.2500 0.38010(15) 0.0311(4) Uani 1 2 d S T P
H7 H 0.4111 0.2500 0.3548 0.037 Uiso 1 2 calc R U P
C8 C 0.56302(16) 0.2500 0.29235(15) 0.0335(4) Uani 1 2 d S T P
H8 H 0.5146 0.2500 0.2060 0.040 Uiso 1 2 calc R U P
C9 C 0.69650(16) 0.2500 0.32600(15) 0.0298(4) Uani 1 2 d S T P
C10 C 0.83403(11) 0.42626(18) 0.73712(10) 0.0348(3) Uani 1 1 d . . .
H10A H 0.7849 0.5437 0.6990 0.042 Uiso 1 1 calc R U .
H10B H 0.9179 0.4320 0.7229 0.042 Uiso 1 1 calc R U .
C11 C 0.85131(12) 0.4209(2) 0.87625(11) 0.0422(4) Uani 1 1 d . . .
H11A H 0.8983 0.5386 0.9167 0.051 Uiso 1 1 calc R U .
H11B H 0.7670 0.4220 0.8897 0.051 Uiso 1 1 calc R U .
C12 C 0.38973(15) 0.2500 0.59584(14) 0.0262(4) Uani 1 2 d S T P
C13 C 0.37044(14) 0.2500 0.72314(14) 0.0269(4) Uani 1 2 d S T P
C14 C 0.24888(16) 0.2500 0.73233(16) 0.0351(4) Uani 1 2 d S T P
H14 H 0.1769 0.2500 0.6591 0.042 Uiso 1 2 calc R U P
C15 C 0.23389(17) 0.2500 0.85040(18) 0.0413(5) Uani 1 2 d S T P
H15 H 0.1515 0.2500 0.8600 0.050 Uiso 1 2 calc R U P
C16 C 0.34058(18) 0.2500 0.95311(17) 0.0426(5) Uani 1 2 d S T P
H16 H 0.3333 0.2500 1.0353 0.051 Uiso 1 2 calc R U P
C17 C 0.45919(17) 0.2500 0.93577(16) 0.0421(5) Uani 1 2 d S T P
H17 H 0.5325 0.2500 1.0077 0.051 Uiso 1 2 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_3
C11 O1 C11 109.89(13) 4_565
C1 N1 C9 117.03(15) .
C5 N2 C10 118.19(7) .
C5 N2 C10 118.19(7) 4_565
C10 N2 C10 111.43(12) 4_565
C12 N3 C6 130.78(13) .
C12 N3 H3 114.6 .
C6 N3 H3 114.6 .
C17 N4 C13 117.09(14) .
N1 C1 C2 124.34(16) .
N1 C1 H1A 117.8 .
C2 C1 H1A 117.8 .
C3 C2 C1 119.04(17) .
C3 C2 H2 120.5 .
C1 C2 H2 120.5 .
C2 C3 C4 119.73(16) .
C2 C3 H3A 120.1 .
C4 C3 H3A 120.1 .
C3 C4 C9 116.61(15) .
C3 C4 C5 124.04(15) .
C9 C4 C5 119.35(14) .
C6 C5 C4 119.61(14) .
C6 C5 N2 116.20(13) .
C4 C5 N2 124.19(13) .
C5 C6 N3 117.14(13) .
C5 C6 C7 120.51(14) .
N3 C6 C7 122.35(14) .
C8 C7 C6 119.95(15) .
C8 C7 H7 120.0 .
C6 C7 H7 120.0 .
C7 C8 C9 121.77(15) .
C7 C8 H8 119.1 .
C9 C8 H8 119.1 .
N1 C9 C8 117.94(15) .
N1 C9 C4 123.25(15) .
C8 C9 C4 118.82(15) .
N2 C10 C11 108.41(11) .
N2 C10 H10A 110.0 .
C11 C10 H10A 110.0 .
N2 C10 H10B 110.0 .
C11 C10 H10B 110.0 .
H10A C10 H10B 108.4 .
O1 C11 C10 110.86(11) .
O1 C11 H11A 109.5 .
C10 C11 H11A 109.5 .
O1 C11 H11B 109.5 .
C10 C11 H11B 109.5 .
H11A C11 H11B 108.1 .
O2 C12 N3 126.14(15) .
O2 C12 C13 121.41(14) .
N3 C12 C13 112.45(13) .
N4 C13 C14 123.46(15) .
N4 C13 C12 116.66(14) .
C14 C13 C12 119.88(14) .
C13 C14 C15 118.68(16) .
C13 C14 H14 120.7 .
C15 C14 H14 120.7 .
C16 C15 C14 118.45(17) .
C16 C15 H15 120.8 .
C14 C15 H15 120.8 .
C15 C16 C17 119.27(16) .
C15 C16 H16 120.4 .
C17 C16 H16 120.4 .
N4 C17 C16 123.05(16) .
N4 C17 H17 118.5 .
C16 C17 H17 118.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C11 1.4284(15) .
O1 C11 1.4284(15) 4_565
O2 C12 1.2241(19) .
N1 C1 1.317(2) .
N1 C9 1.370(2) .
N2 C5 1.4317(19) .
N2 C10 1.4599(14) .
N2 C10 1.4599(13) 4_565
N3 C12 1.348(2) .
N3 C6 1.395(2) .
N3 H3 0.8800 .
N4 C17 1.335(2) .
N4 C13 1.337(2) .
C1 C2 1.403(3) .
C1 H1A 0.9500 .
C2 C3 1.366(2) .
C2 H2 0.9500 .
C3 C4 1.415(2) .
C3 H3A 0.9500 .
C4 C9 1.424(2) .
C4 C5 1.424(2) .
C5 C6 1.387(2) .
C6 C7 1.417(2) .
C7 C8 1.360(2) .
C7 H7 0.9500 .
C8 C9 1.406(2) .
C8 H8 0.9500 .
C10 C11 1.5121(16) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.507(2) .
C13 C14 1.380(2) .
C14 C15 1.384(3) .
C14 H14 0.9500 .
C15 C16 1.370(3) .
C15 H15 0.9500 .
C16 C17 1.385(3) .
C16 H16 0.9500 .
C17 H17 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11A O1 0.99 2.63 3.5671(16) 158.9 3_767
C10 H10A O2 0.99 2.55 3.4187(14) 145.9 3_666
C7 H7 O2 0.95 2.32 2.938(2) 121.9 .
N3 H3 N4 0.88 2.14 2.6224(19) 114.0 .
N3 H3 N2 0.88 2.21 2.6554(17) 111.2 .
C11 H11A O1 0.99 2.63 3.5671(16) 158.9 3_767
C10 H10A O2 0.99 2.55 3.4187(14) 145.9 3_666
C7 H7 O2 0.95 2.32 2.938(2) 121.9 .
N3 H3 N4 0.88 2.14 2.6224(19) 114.0 .
N3 H3 N2 0.88 2.21 2.6554(17) 111.2 .
N3 H3 N2 0.88 2.21 2.6554(17) 111.2 .
N3 H3 N4 0.88 2.14 2.6224(19) 114.0 .
C7 H7 O2 0.95 2.32 2.938(2) 121.9 .
C10 H10A O2 0.99 2.55 3.4187(14) 145.9 3_666
C11 H11A O1 0.99 2.63 3.5671(16) 158.9 3_767
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
C9 N1 C1 C2 0.000(0) .
N1 C1 C2 C3 0.000(0) .
C1 C2 C3 C4 0.000(0) .
C2 C3 C4 C9 0.000(0) .
C2 C3 C4 C5 180.000(0) .
C3 C4 C5 C6 180.000(0) .
C9 C4 C5 C6 0.000(0) .
C3 C4 C5 N2 0.000(0) .
C9 C4 C5 N2 180.000(0) .
C10 N2 C5 C6 -110.37(10) .
C10 N2 C5 C6 110.37(10) 4_565
C10 N2 C5 C4 69.63(10) .
C10 N2 C5 C4 -69.63(10) 4_565
C4 C5 C6 N3 180.000(0) .
N2 C5 C6 N3 0.000(0) .
C4 C5 C6 C7 0.000(0) .
N2 C5 C6 C7 180.000(0) .
C12 N3 C6 C5 180.000(0) .
C12 N3 C6 C7 0.000(1) .
C5 C6 C7 C8 0.000(0) .
N3 C6 C7 C8 180.000(0) .
C6 C7 C8 C9 0.000(0) .
C1 N1 C9 C8 180.000(0) .
C1 N1 C9 C4 0.000(0) .
C7 C8 C9 N1 180.000(0) .
C7 C8 C9 C4 0.000(0) .
C3 C4 C9 N1 0.000(0) .
C5 C4 C9 N1 180.000(0) .
C3 C4 C9 C8 180.000(0) .
C5 C4 C9 C8 0.000(0) .
C5 N2 C10 C11 160.44(11) .
C10 N2 C10 C11 -57.72(16) 4_565
C11 O1 C11 C10 -60.17(18) 4_565
N2 C10 C11 O1 58.34(14) .
C6 N3 C12 O2 0.000(1) .
C6 N3 C12 C13 180.000(0) .
C17 N4 C13 C14 0.000(1) .
C17 N4 C13 C12 180.000(1) .
O2 C12 C13 N4 180.000(1) .
N3 C12 C13 N4 0.000(1) .
O2 C12 C13 C14 0.000(1) .
N3 C12 C13 C14 180.000(1) .
N4 C13 C14 C15 0.000(1) .
C12 C13 C14 C15 180.000(1) .
C13 C14 C15 C16 0.000(1) .
C14 C15 C16 C17 0.000(1) .
C13 N4 C17 C16 0.000(1) .
C15 C16 C17 N4 0.000(1) .
