#------------------------------------------------------------------------------
#$Date: 2019-11-17 04:57:53 +0200 (Sun, 17 Nov 2019) $
#$Revision: 227993 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/23/7122313.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_7122313
loop_
_publ_author_name
'Yuan, Zaifeng'
'Zhu, Chunyu'
'Ma, Zhixian'
'Xia, Chengfeng'
_publ_section_title
;
 Copper-catalyzed amination of an α-C(sp³)-H bond in
 inactivated ethers to synthesize α-aminonitriles.
;
_journal_issue                   78
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11033
_journal_page_last               11036
_journal_paper_doi               10.1039/c8cc06111d
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C11 H12 Cl N2 O'
_chemical_formula_weight         223.68
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-04-09 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.338(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8906(18)
_cell_length_b                   8.8166(14)
_cell_length_c                   11.2785(17)
_cell_measurement_reflns_used    1587
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.4371
_cell_measurement_theta_min      2.9093
_cell_volume                     1145.5(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0261
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6314
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.149
_diffrn_reflns_theta_max         25.149
_diffrn_reflns_theta_min         1.768
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0456
_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)+(0.1000P)²+0.1879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1588
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1432
_reflns_number_total             2047
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc06111d2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7122313.cif.'
_cod_database_code               7122313
_shelx_shelxl_version_number     2014/7
_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   0.913
_shelx_estimated_absorpt_t_max   0.941
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
Cl1 Cl 1.18872(7) 0.17503(9) 0.30116(8) 0.0876(4) Uani 1 1 d . .
N1 N 0.75741(17) 0.1337(2) 0.46945(19) 0.0581(6) Uani 1 1 d . .
H1A H 0.7106 0.0625 0.4367 0.070 Uiso 1 1 calc R U
N2 N 0.6857(2) 0.5058(3) 0.4696(3) 0.0832(8) Uani 1 1 d . .
O1 O 0.36677(15) 0.16358(19) 0.60380(19) 0.0720(6) Uani 1 1 d . .
H1 H 0.3364 0.2442 0.5770 0.108 Uiso 1 1 calc R U
C1 C 1.0630(2) 0.1653(3) 0.3538(2) 0.0572(7) Uani 1 1 d . .
C2 C 1.0440(2) 0.2669(3) 0.4389(2) 0.0573(6) Uani 1 1 d . .
H2 H 1.0991 0.3411 0.4699 0.069 Uiso 1 1 calc R U
C3 C 0.9432(2) 0.2591(3) 0.4783(2) 0.0528(6) Uani 1 1 d . .
H3 H 0.9306 0.3291 0.5354 0.063 Uiso 1 1 calc R U
C4 C 0.8598(2) 0.1476(2) 0.4338(2) 0.0463(5) Uani 1 1 d . .
C5 C 0.8814(2) 0.0456(3) 0.3479(2) 0.0585(6) Uani 1 1 d . .
H5 H 0.8270 -0.0293 0.3166 0.070 Uiso 1 1 calc R U
C6 C 0.9815(2) 0.0539(3) 0.3085(2) 0.0622(7) Uani 1 1 d . .
H6 H 0.9947 -0.0154 0.2513 0.075 Uiso 1 1 calc R U
C7 C 0.7235(2) 0.2292(3) 0.5569(2) 0.0535(6) Uani 1 1 d . .
H7 H 0.7857 0.2309 0.6324 0.064 Uiso 1 1 calc R U
C8 C 0.6114(2) 0.1658(3) 0.5853(3) 0.0639(7) Uani 1 1 d . .
H8A H 0.5523 0.1554 0.5091 0.077 Uiso 1 1 calc R U
H8B H 0.6275 0.0654 0.6206 0.077 Uiso 1 1 calc R U
C9 C 0.5647(2) 0.2624(3) 0.6708(3) 0.0692(7) Uani 1 1 d . .
H9A H 0.5425 0.3602 0.6329 0.083 Uiso 1 1 calc R U
H9B H 0.6253 0.2792 0.7448 0.083 Uiso 1 1 calc R U
C10 C 0.4617(2) 0.1920(3) 0.7039(3) 0.0746(8) Uani 1 1 d . .
H10A H 0.4857 0.0970 0.7459 0.090 Uiso 1 1 calc R U
H10B H 0.4364 0.2586 0.7606 0.090 Uiso 1 1 calc R U
C11 C 0.7028(2) 0.3861(3) 0.5080(2) 0.0596(7) Uani 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'
Cl Cl 0.1484 0.1585 '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
C4 N1 C7 124.72(19)
C4 N1 H1A 117.6
C7 N1 H1A 117.6
C10 O1 H1 109.5
C2 C1 C6 120.0(2)
C2 C1 Cl1 120.7(2)
C6 C1 Cl1 119.4(2)
C1 C2 C3 120.0(2)
C1 C2 H2 120.0
C3 C2 H2 120.0
C2 C3 C4 121.0(2)
C2 C3 H3 119.5
C4 C3 H3 119.5
N1 C4 C5 118.3(2)
N1 C4 C3 123.8(2)
C5 C4 C3 117.8(2)
C6 C5 C4 121.0(2)
C6 C5 H5 119.5
C4 C5 H5 119.5
C5 C6 C1 120.2(2)
C5 C6 H6 119.9
C1 C6 H6 119.9
N1 C7 C11 110.0(2)
N1 C7 C8 109.5(2)
C11 C7 C8 109.89(19)
N1 C7 H7 109.1
C11 C7 H7 109.1
C8 C7 H7 109.1
C9 C8 C7 113.8(2)
C9 C8 H8A 108.8
C7 C8 H8A 108.8
C9 C8 H8B 108.8
C7 C8 H8B 108.8
H8A C8 H8B 107.7
C8 C9 C10 112.5(2)
C8 C9 H9A 109.1
C10 C9 H9A 109.1
C8 C9 H9B 109.1
C10 C9 H9B 109.1
H9A C9 H9B 107.8
O1 C10 C9 114.6(2)
O1 C10 H10A 108.6
C9 C10 H10A 108.6
O1 C10 H10B 108.6
C9 C10 H10B 108.6
H10A C10 H10B 107.6
N2 C11 C7 179.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.742(3)
N1 C4 1.378(3)
N1 C7 1.428(3)
N1 H1A 0.8600
N2 C11 1.140(3)
O1 C10 1.407(3)
O1 H1 0.8200
C1 C2 1.372(4)
C1 C6 1.386(4)
C2 C3 1.380(3)
C2 H2 0.9300
C3 C4 1.399(3)
C3 H3 0.9300
C4 C5 1.392(3)
C5 C6 1.371(4)
C5 H5 0.9300
C6 H6 0.9300
C7 C11 1.487(4)
C7 C8 1.550(3)
C7 H7 0.9800
C8 C9 1.492(4)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.501(4)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9700
C10 H10B 0.9700
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
C5 H5 Cl1 0.93 2.91 3.674(3) 140.3 2_745
O1 H1 N2 0.82 2.27 3.052(3) 160.7 3_666
N1 H1A O1 0.86 2.20 3.022(3) 161.1 3_656
C5 H5 Cl1 0.93 2.91 3.674(3) 140.3 2_745
O1 H1 N2 0.82 2.27 3.052(3) 160.7 3_666
O1 H1 N2 0.82 2.27 3.052(3) 160.7 3_666
C5 H5 Cl1 0.93 2.91 3.674(3) 140.3 2_745
O1 H1 N2 0.82 2.27 3.052(3) 160.7 3_666
C5 H5 Cl1 0.93 2.91 3.674(3) 140.3 2_745
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
C6 C1 C2 C3 -0.6(3)
Cl1 C1 C2 C3 179.04(17)
C1 C2 C3 C4 0.7(3)
C7 N1 C4 C5 179.7(2)
C7 N1 C4 C3 -0.8(3)
C2 C3 C4 N1 -180.0(2)
C2 C3 C4 C5 -0.5(3)
N1 C4 C5 C6 179.8(2)
C3 C4 C5 C6 0.3(3)
C4 C5 C6 C1 -0.3(4)
C2 C1 C6 C5 0.4(4)
Cl1 C1 C6 C5 -179.24(18)
C4 N1 C7 C11 66.5(3)
C4 N1 C7 C8 -172.6(2)
N1 C7 C8 C9 -176.8(2)
C11 C7 C8 C9 -55.8(3)
C7 C8 C9 C10 -175.6(2)
C8 C9 C10 O1 -59.6(3)
