#------------------------------------------------------------------------------
#$Date: 2017-01-09 08:35:21 +0200 (Mon, 09 Jan 2017) $
#$Revision: 190258 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/53/7155332.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_7155332
loop_
_publ_author_name
'Li, Jiawen'
'Qin, Guiping'
'Huang, Hanmin'
_publ_section_title
;
 Silver-catalyzed nucleophilic substitution of aminals with ethyl
 diazoacetate: a new pathway to β-amino-α-diazoesters.
;
_journal_issue                   45
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              10572
_journal_page_last               10575
_journal_paper_doi               10.1039/c6ob02136k
_journal_volume                  14
_journal_year                    2016
_chemical_formula_sum            'C15 H18 Cl N3 O3'
_chemical_formula_weight         323.77
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-09-04 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.732(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.309(5)
_cell_length_b                   14.264(7)
_cell_length_c                   10.935(5)
_cell_measurement_reflns_used    2544
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.60
_cell_measurement_theta_min      2.36
_cell_volume                     1589.3(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SMART'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7833
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.9626
_exptl_absorpt_correction_T_min  0.9271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2784
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0900P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1435
_refine_ls_wR_factor_ref         0.1601
_reflns_number_gt                2081
_reflns_number_total             2784
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob02136k2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155331--7155332.cif.
;
_cod_original_cell_volume        1589.5(13)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7155332
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.41377(9) 0.18858(6) 0.25101(6) 0.0786(3) Uani 1 1 d .
O1 O 0.6112(2) 0.02845(14) 0.84387(18) 0.0677(6) Uani 1 1 d .
O2 O 0.1898(2) 0.06202(14) 0.4326(2) 0.0807(7) Uani 1 1 d .
O3 O 0.05829(16) 0.17977(13) 0.46933(19) 0.0591(5) Uani 1 1 d .
N1 N 0.48552(18) 0.15087(14) 0.65630(18) 0.0425(5) Uani 1 1 d .
N2 N 0.2500(2) 0.27991(16) 0.56719(18) 0.0483(5) Uani 1 1 d .
N3 N 0.2290(3) 0.3509(2) 0.6032(3) 0.0762(8) Uani 1 1 d .
C2 C 0.4931(2) 0.25688(15) 0.4805(2) 0.0417(5) Uani 1 1 d .
C3 C 0.5576(3) 0.32394(18) 0.5580(3) 0.0564(7) Uani 1 1 d .
H3 H 0.5610 0.3179 0.6431 0.068 Uiso 1 1 calc R
C4 C 0.6175(3) 0.4004(2) 0.5108(3) 0.0707(6) Uani 1 1 d U
H4 H 0.6619 0.4445 0.5641 0.085 Uiso 1 1 calc R
C5 C 0.6110(3) 0.4103(2) 0.3859(3) 0.0701(6) Uani 1 1 d U
H5 H 0.6498 0.4620 0.3545 0.084 Uiso 1 1 calc R
C6 C 0.5489(3) 0.3461(2) 0.3075(3) 0.0680(6) Uani 1 1 d U
H6 H 0.5447 0.3533 0.2225 0.082 Uiso 1 1 calc R
C7 C 0.4914(2) 0.26932(19) 0.3550(2) 0.0495(6) Uani 1 1 d .
C8 C 0.4238(2) 0.17541(15) 0.5310(2) 0.0403(5) Uani 1 1 d .
H8 H 0.4307 0.1211 0.4776 0.048 Uiso 1 1 calc R
C9 C 0.1751(2) 0.13910(18) 0.4710(2) 0.0510(6) Uani 1 1 d .
C10 C -0.0562(3) 0.1262(2) 0.4152(4) 0.0812(10) Uani 1 1 d .
H10A H -0.0460 0.1057 0.3326 0.097 Uiso 1 1 calc R
H10B H -0.0655 0.0710 0.4651 0.097 Uiso 1 1 calc R
C11 C -0.1701(3) 0.1839(3) 0.4099(4) 0.0904(11) Uani 1 1 d .
H11A H -0.1715 0.2126 0.4891 0.136 Uiso 1 1 calc R
H11B H -0.2474 0.1463 0.3885 0.136 Uiso 1 1 calc R
H11C H -0.1680 0.2318 0.3484 0.136 Uiso 1 1 calc R
C12 C 0.2806(2) 0.19867(16) 0.5252(2) 0.0429(6) Uani 1 1 d .
C13 C 0.4132(3) 0.08071(19) 0.7157(3) 0.0555(7) Uani 1 1 d .
H13A H 0.4068 0.0232 0.6678 0.067 Uiso 1 1 calc R
H13B H 0.3250 0.1031 0.7192 0.067 Uiso 1 1 calc R
C14 C 0.4821(3) 0.0618(2) 0.8437(3) 0.0659(8) Uani 1 1 d .
H14A H 0.4852 0.1190 0.8919 0.079 Uiso 1 1 calc R
H14B H 0.4327 0.0157 0.8828 0.079 Uiso 1 1 calc R
C15 C 0.6830(3) 0.0933(2) 0.7830(3) 0.0653(8) Uani 1 1 d .
H15A H 0.7699 0.0684 0.7800 0.078 Uiso 1 1 calc R
H15B H 0.6929 0.1512 0.8300 0.078 Uiso 1 1 calc R
C16 C 0.6175(3) 0.1139(2) 0.6544(2) 0.0535(6) Uani 1 1 d .
H16A H 0.6690 0.1593 0.6165 0.064 Uiso 1 1 calc R
H16B H 0.6122 0.0569 0.6054 0.064 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 0.0000 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
C14 O1 C15 109.9(2)
C9 O3 C10 116.9(2)
C13 N1 C16 107.3(2)
C13 N1 C8 113.73(19)
C16 N1 C8 110.27(18)
N3 N2 C12 177.2(3)
C3 C2 C7 117.0(2)
C3 C2 C8 121.2(2)
C7 C2 C8 121.8(2)
C2 C3 C4 121.0(3)
C2 C3 H3 119.5
C4 C3 H3 119.5
C5 C4 C3 119.7(3)
C5 C4 H4 120.1
C3 C4 H4 120.1
C6 C5 C4 120.8(3)
C6 C5 H5 119.6
C4 C5 H5 119.6
C5 C6 C7 119.2(3)
C5 C6 H6 120.4
C7 C6 H6 120.4
C2 C7 C6 122.2(3)
C2 C7 Cl1 120.2(2)
C6 C7 Cl1 117.6(2)
N1 C8 C12 112.13(18)
N1 C8 C2 111.32(18)
C12 C8 C2 109.28(18)
N1 C8 H8 108.0
C12 C8 H8 108.0
C2 C8 H8 108.0
O2 C9 O3 123.9(2)
O2 C9 C12 124.1(2)
O3 C9 C12 112.0(2)
C11 C10 O3 108.9(3)
C11 C10 H10A 109.9
O3 C10 H10A 109.9
C11 C10 H10B 109.9
O3 C10 H10B 109.9
H10A C10 H10B 108.3
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
N2 C12 C9 117.6(2)
N2 C12 C8 118.0(2)
C9 C12 C8 124.3(2)
N1 C13 C14 109.8(2)
N1 C13 H13A 109.7
C14 C13 H13A 109.7
N1 C13 H13B 109.7
C14 C13 H13B 109.7
H13A C13 H13B 108.2
O1 C14 C13 112.0(2)
O1 C14 H14A 109.2
C13 C14 H14A 109.2
O1 C14 H14B 109.2
C13 C14 H14B 109.2
H14A C14 H14B 107.9
O1 C15 C16 112.2(2)
O1 C15 H15A 109.2
C16 C15 H15A 109.2
O1 C15 H15B 109.2
C16 C15 H15B 109.2
H15A C15 H15B 107.9
N1 C16 C15 110.2(2)
N1 C16 H16A 109.6
C15 C16 H16A 109.6
N1 C16 H16B 109.6
C15 C16 H16B 109.6
H16A C16 H16B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C7 1.727(3)
O1 C14 1.413(3)
O1 C15 1.413(3)
O2 C9 1.195(3)
O3 C9 1.334(3)
O3 C10 1.455(3)
N1 C13 1.458(3)
N1 C16 1.462(3)
N1 C8 1.463(3)
N2 N3 1.120(3)
N2 C12 1.303(3)
C2 C3 1.380(4)
C2 C7 1.382(3)
C2 C8 1.512(3)
C3 C4 1.391(4)
C3 H3 0.9300
C4 C5 1.364(5)
C4 H4 0.9300
C5 C6 1.348(5)
C5 H5 0.9300
C6 C7 1.383(4)
C6 H6 0.9300
C8 C12 1.505(3)
C8 H8 0.9800
C9 C12 1.435(4)
C10 C11 1.429(5)
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C13 C14 1.495(4)
C13 H13A 0.9700
C13 H13B 0.9700
C14 H14A 0.9700
C14 H14B 0.9700
C15 C16 1.494(4)
C15 H15A 0.9700
C15 H15B 0.9700
C16 H16A 0.9700
C16 H16B 0.9700
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
C7 C2 C3 C4 0.1(4)
C8 C2 C3 C4 -177.9(2)
C2 C3 C4 C5 1.1(4)
C3 C4 C5 C6 -1.1(5)
C4 C5 C6 C7 0.0(5)
C3 C2 C7 C6 -1.3(4)
C8 C2 C7 C6 176.7(2)
C3 C2 C7 Cl1 179.66(19)
C8 C2 C7 Cl1 -2.4(3)
C5 C6 C7 C2 1.3(4)
C5 C6 C7 Cl1 -179.7(2)
C13 N1 C8 C12 49.9(3)
C16 N1 C8 C12 170.6(2)
C13 N1 C8 C2 172.7(2)
C16 N1 C8 C2 -66.7(2)
C3 C2 C8 N1 -28.7(3)
C7 C2 C8 N1 153.4(2)
C3 C2 C8 C12 95.7(3)
C7 C2 C8 C12 -82.2(3)
C10 O3 C9 O2 -1.0(4)
C10 O3 C9 C12 179.4(3)
C9 O3 C10 C11 -174.1(3)
N3 N2 C12 C9 -163(5)
N3 N2 C12 C8 14(5)
O2 C9 C12 N2 -177.7(3)
O3 C9 C12 N2 1.9(3)
O2 C9 C12 C8 5.4(4)
O3 C9 C12 C8 -175.0(2)
N1 C8 C12 N2 75.9(3)
C2 C8 C12 N2 -48.1(3)
N1 C8 C12 C9 -107.3(3)
C2 C8 C12 C9 128.8(2)
C16 N1 C13 C14 58.9(3)
C8 N1 C13 C14 -178.8(2)
C15 O1 C14 C13 56.7(3)
N1 C13 C14 O1 -59.7(3)
C14 O1 C15 C16 -56.1(3)
C13 N1 C16 C15 -58.4(3)
C8 N1 C16 C15 177.2(2)
O1 C15 C16 N1 58.4(3)
