#------------------------------------------------------------------------------
#$Date: 2020-04-08 02:25:46 +0300 (Wed, 08 Apr 2020) $
#$Revision: 250459 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038202.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_4038202
loop_
_publ_author_name
'Chen, Yuepeng'
'Liu, Xinglei'
'Shi, Wei'
'Zheng, Shilong'
'Wang, Guangdi'
'He, Ling'
_publ_section_title
;
 One-Pot Synthesis of Seven-Membered Heterocyclic Derivatives of
 Diazepines Involving Copper-Catalyzed Rearrangement Cascade
 Allyl-Amination.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02710
_journal_year                    2020
_chemical_formula_sum            'C18 H18 N2 O'
_chemical_formula_weight         278.34
_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   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 96.144(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1061(18)
_cell_length_b                   11.735(3)
_cell_length_c                   18.004(4)
_cell_measurement_reflns_used    2168
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.463
_cell_measurement_theta_min      5.724
_cell_volume                     1492.7(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8686
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.075
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2926
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0481
_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)+(0.0566P)²+0.1165P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1223
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2173
_reflns_number_total             2926
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b02710_si_001.cif
_cod_data_source_block           cd16594
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038202
_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   0.983
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.11039(17) 0.63395(10) 0.22646(7) 0.0441(3) Uani 1 1 d . . . . .
N2 N 0.4297(2) 0.79517(12) 0.23287(8) 0.0547(4) Uani 1 1 d . . . . .
O1 O 0.23893(15) 0.46652(9) 0.26666(6) 0.0553(3) Uani 1 1 d . . . . .
C1 C 0.4777(2) 0.73411(12) 0.29769(8) 0.0440(4) Uani 1 1 d . . . . .
C2 C 0.6372(2) 0.77023(14) 0.34431(9) 0.0553(5) Uani 1 1 d . . . . .
H2 H 0.6994 0.8363 0.3323 0.066 Uiso 1 1 calc R U . . .
C3 C 0.7034(3) 0.71107(16) 0.40678(10) 0.0682(6) Uani 1 1 d . . . . .
H3 H 0.8091 0.7377 0.4367 0.082 Uiso 1 1 calc R U . . .
C4 C 0.6160(3) 0.61254(17) 0.42613(10) 0.0708(6) Uani 1 1 d . . . . .
H4 H 0.6597 0.5732 0.4694 0.085 Uiso 1 1 calc R U . . .
C5 C 0.4643(3) 0.57373(15) 0.38055(9) 0.0577(5) Uani 1 1 d . . . . .
H5 H 0.4068 0.5061 0.3928 0.069 Uiso 1 1 calc R U . . .
C6 C 0.3920(2) 0.63183(13) 0.31619(8) 0.0432(4) Uani 1 1 d . . . . .
C7 C 0.2423(2) 0.57115(13) 0.26810(8) 0.0431(4) Uani 1 1 d . . . . .
C8 C 0.0950(2) 0.75631(13) 0.23912(9) 0.0513(4) Uani 1 1 d . . . . .
H8A H 0.1122 0.7711 0.2924 0.062 Uiso 1 1 calc R U . . .
H8B H -0.0311 0.7815 0.2202 0.062 Uiso 1 1 calc R U . . .
C9 C 0.2389(2) 0.82417(13) 0.20175(9) 0.0510(5) Uani 1 1 d . . . . .
H9 H 0.2196 0.9042 0.2145 0.061 Uiso 1 1 calc R U . . .
C10 C 0.2107(3) 0.81671(15) 0.11821(10) 0.0622(5) Uani 1 1 d . U . . .
C11 C 0.3376(4) 0.77453(18) 0.07903(12) 0.0836(6) Uani 1 1 d . U . . .
H11A H 0.3167 0.7744 0.0271 0.100 Uiso 1 1 calc R U . . .
H11B H 0.4492 0.7445 0.1029 0.100 Uiso 1 1 calc R U . . .
C12 C 0.0296(4) 0.8659(2) 0.08261(13) 0.1073(9) Uani 1 1 d . . . . .
H12A H 0.0345 0.8718 0.0297 0.161 Uiso 1 1 calc R U . . .
H12B H 0.0113 0.9402 0.1029 0.161 Uiso 1 1 calc R U . . .
H12C H -0.0737 0.8173 0.0923 0.161 Uiso 1 1 calc R U . . .
C13 C -0.0318(2) 0.57676(12) 0.17745(8) 0.0435(4) Uani 1 1 d . . . . .
C14 C -0.2185(2) 0.58539(15) 0.18943(10) 0.0580(5) Uani 1 1 d . . . . .
H14 H -0.2531 0.6294 0.2287 0.070 Uiso 1 1 calc R U . . .
C15 C -0.3545(3) 0.52895(17) 0.14338(12) 0.0700(6) Uani 1 1 d . . . . .
H15 H -0.4811 0.5356 0.1515 0.084 Uiso 1 1 calc R U . . .
C16 C -0.3057(3) 0.46341(16) 0.08603(11) 0.0665(5) Uani 1 1 d . . . . .
H16 H -0.3984 0.4250 0.0553 0.080 Uiso 1 1 calc R U . . .
C17 C -0.1201(3) 0.45458(15) 0.07404(10) 0.0620(5) Uani 1 1 d . . . . .
H17 H -0.0861 0.4095 0.0351 0.074 Uiso 1 1 calc R U . . .
C18 C 0.0178(2) 0.51200(14) 0.11913(9) 0.0510(4) Uani 1 1 d . . . . .
H18 H 0.1439 0.5068 0.1100 0.061 Uiso 1 1 calc R U . . .
H2A H 0.511(3) 0.8516(15) 0.2283(9) 0.058(5) Uiso 1 1 d . . . . .
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
_geom_angle_publ_flag
C7 N1 C13 119.08(12) . . ?
C7 N1 C8 120.52(11) . . ?
C13 N1 C8 119.78(11) . . ?
C1 N2 C9 125.76(15) . . ?
C1 N2 H2A 111.0(11) . . ?
C9 N2 H2A 112.4(11) . . ?
N2 C1 C2 117.40(15) . . ?
N2 C1 C6 124.79(13) . . ?
C2 C1 C6 117.43(13) . . ?
C3 C2 C1 121.75(16) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 120.82(16) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.59(16) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 122.34(17) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C1 119.02(14) . . ?
C5 C6 C7 115.38(14) . . ?
C1 C6 C7 125.18(13) . . ?
O1 C7 N1 121.44(13) . . ?
O1 C7 C6 120.30(13) . . ?
N1 C7 C6 118.26(13) . . ?
N1 C8 C9 112.57(14) . . ?
N1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N2 C9 C10 113.13(16) . . ?
N2 C9 C8 110.70(13) . . ?
C10 C9 C8 113.10(13) . . ?
N2 C9 H9 106.5 . . ?
C10 C9 H9 106.5 . . ?
C8 C9 H9 106.5 . . ?
C11 C10 C12 122.1(2) . . ?
C11 C10 C9 122.72(18) . . ?
C12 C10 C9 115.2(2) . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 119.55(15) . . ?
C14 C13 N1 119.90(15) . . ?
C18 C13 N1 120.55(14) . . ?
C13 C14 C15 119.97(18) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.69(18) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.47(17) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.53(18) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 119.78(17) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.3541(18) . ?
N1 C13 1.4348(18) . ?
N1 C8 1.4598(19) . ?
N2 C1 1.3807(19) . ?
N2 C9 1.451(2) . ?
N2 H2A 0.891(18) . ?
O1 C7 1.2283(18) . ?
C1 C2 1.402(2) . ?
C1 C6 1.402(2) . ?
C2 C3 1.362(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.480(2) . ?
C8 C9 1.510(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.499(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.301(3) . ?
C10 C12 1.491(3) . ?
C11 H11A 0.9300 . ?
C11 H11B 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.371(2) . ?
C13 C18 1.372(2) . ?
C14 C15 1.374(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.362(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
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
N2 H2A O1 0.891(18) 2.222(18) 3.096(2) 166.7(15) 2_655
C8 H8B O1 0.97 2.65 3.417(2) 136.2 2
C2 H2 O1 0.93 2.42 3.233(2) 145.6 2_655
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N2 C1 C2 -140.20(16) . . . . ?
C9 N2 C1 C6 47.2(2) . . . . ?
N2 C1 C2 C3 -175.45(17) . . . . ?
C6 C1 C2 C3 -2.3(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 C6 -1.6(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C7 172.73(18) . . . . ?
N2 C1 C6 C5 174.75(16) . . . . ?
C2 C1 C6 C5 2.1(2) . . . . ?
N2 C1 C6 C7 2.5(3) . . . . ?
C2 C1 C6 C7 -170.09(15) . . . . ?
C13 N1 C7 O1 -2.5(2) . . . . ?
C8 N1 C7 O1 168.42(15) . . . . ?
C13 N1 C7 C6 177.76(14) . . . . ?
C8 N1 C7 C6 -11.3(2) . . . . ?
C5 C6 C7 O1 -28.9(2) . . . . ?
C1 C6 C7 O1 143.59(16) . . . . ?
C5 C6 C7 N1 150.84(15) . . . . ?
C1 C6 C7 N1 -36.7(2) . . . . ?
C7 N1 C8 C9 81.12(18) . . . . ?
C13 N1 C8 C9 -108.01(15) . . . . ?
C1 N2 C9 C10 -141.34(16) . . . . ?
C1 N2 C9 C8 -13.2(2) . . . . ?
N1 C8 C9 N2 -63.28(16) . . . . ?
N1 C8 C9 C10 64.88(17) . . . . ?
N2 C9 C10 C11 8.3(2) . . . . ?
C8 C9 C10 C11 -118.6(2) . . . . ?
N2 C9 C10 C12 -169.17(16) . . . . ?
C8 C9 C10 C12 63.9(2) . . . . ?
C7 N1 C13 C14 116.28(17) . . . . ?
C8 N1 C13 C14 -54.7(2) . . . . ?
C7 N1 C13 C18 -62.8(2) . . . . ?
C8 N1 C13 C18 126.20(16) . . . . ?
C18 C13 C14 C15 0.3(2) . . . . ?
N1 C13 C14 C15 -178.79(15) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C14 C13 C18 C17 -1.2(2) . . . . ?
N1 C13 C18 C17 177.88(14) . . . . ?
C16 C17 C18 C13 1.3(3) . . . . ?
