#------------------------------------------------------------------------------
#$Date: 2016-04-04 15:05:16 +0300 (Mon, 04 Apr 2016) $
#$Revision: 181457 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/27/1542745.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_1542745
loop_
_publ_author_name
'Zhu, Chuanle'
'Li, Jiawei'
'Chen, Pengquan'
'Wu, Wanqing'
'Ren, Yanwei'
'Jiang, Huanfeng'
_publ_section_title
;
 Transition-Metal-Free Cyclopropanation of 2-Aminoacrylates with
 N-Tosylhydrazones: A General Route to Cyclopropane α-Amino Acid with
 Contiguous Quaternary Carbon Centers.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1470
_journal_page_last               1473
_journal_paper_doi               10.1021/acs.orglett.6b00416
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C16 H19 N O5'
_chemical_formula_weight         305.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.42(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8082(18)
_cell_length_b                   19.624(4)
_cell_length_c                   9.7487(19)
_cell_measurement_reflns_used    11292
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.03
_cell_measurement_theta_min      6.23
_cell_volume                     1677.5(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  Rigaku
_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  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18879
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.9910
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.026(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0652
_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)+(0.1435P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1822
_refine_ls_wR_factor_ref         0.2244
_reflns_number_gt                1491
_reflns_number_total             2950
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00416_si_002.cif
_cod_data_source_block           z-2
_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/ACS/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 1542744--1542745.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1542745
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.2360(3) 0.71493(11) 0.7805(2) 0.0672(7) Uani 1 1 d .
H1A H 0.2358 0.7238 0.6941 0.081 Uiso 1 1 calc R
C1 C 0.3103(4) 0.40026(14) 0.6431(3) 0.0716(8) Uani 1 1 d .
O5 O 0.1991(3) 0.75334(12) 0.99087(19) 0.0929(8) Uani 1 1 d .
C12 C 0.2753(4) 0.64811(13) 0.8293(2) 0.0663(8) Uani 1 1 d .
C15 C 0.1996(4) 0.76423(14) 0.8667(3) 0.0688(8) Uani 1 1 d .
C5 C 0.4536(4) 0.48331(16) 0.7805(3) 0.0800(9) Uani 1 1 d .
H5A H 0.5333 0.4934 0.8469 0.096 Uiso 1 1 calc R
O3 O 0.0134(3) 0.62369(12) 0.8197(2) 0.0955(8) Uani 1 1 d .
O2 O 0.1842(3) 0.32111(11) 0.4937(3) 0.0958(8) Uani 1 1 d .
C10 C 0.3940(3) 0.60908(14) 0.7558(2) 0.0685(8) Uani 1 1 d .
C3 C 0.2456(4) 0.51878(15) 0.6234(3) 0.0805(9) Uani 1 1 d .
H3A H 0.1834 0.5531 0.5834 0.097 Uiso 1 1 calc R
C4 C 0.3640(3) 0.53529(14) 0.7231(3) 0.0686(8) Uani 1 1 d .
O4 O 0.1712(3) 0.56137(14) 0.9622(2) 0.1096(9) Uani 1 1 d .
C8 C 0.2902(4) 0.32825(17) 0.5982(3) 0.0816(9) Uani 1 1 d .
C13 C 0.1499(4) 0.60642(16) 0.8801(3) 0.0787(9) Uani 1 1 d .
C2 C 0.2198(4) 0.45192(16) 0.5836(3) 0.0830(9) Uani 1 1 d .
H2A H 0.1411 0.4416 0.5164 0.100 Uiso 1 1 calc R
C6 C 0.4276(4) 0.41722(17) 0.7419(3) 0.0837(9) Uani 1 1 d .
H6A H 0.4896 0.3830 0.7826 0.100 Uiso 1 1 calc R
O1 O 0.3650(4) 0.28208(13) 0.6502(3) 0.1199(10) Uani 1 1 d .
C17 C 0.4711(4) 0.64579(17) 0.6441(3) 0.0816(9) Uani 1 1 d .
H17A H 0.5423 0.6156 0.6065 0.122 Uiso 1 1 calc R
H17B H 0.5243 0.6850 0.6828 0.122 Uiso 1 1 calc R
H17C H 0.3956 0.6599 0.5723 0.122 Uiso 1 1 calc R
C11 C 0.4314(4) 0.63380(17) 0.8990(3) 0.0825(9) Uani 1 1 d .
H11A H 0.5016 0.6718 0.9128 0.099 Uiso 1 1 calc R
H11B H 0.4398 0.6001 0.9721 0.099 Uiso 1 1 calc R
C16 C 0.1595(4) 0.83180(16) 0.8044(3) 0.0859(9) Uani 1 1 d .
H16A H 0.1361 0.8630 0.8753 0.129 Uiso 1 1 calc R
H16B H 0.0723 0.8271 0.7381 0.129 Uiso 1 1 calc R
H16C H 0.2441 0.8489 0.7595 0.129 Uiso 1 1 calc R
C14 C -0.1126(5) 0.5823(2) 0.8609(6) 0.1367(17) Uani 1 1 d .
H14A H -0.2066 0.5979 0.8134 0.205 Uiso 1 1 calc R
H14B H -0.1176 0.5863 0.9585 0.205 Uiso 1 1 calc R
H14C H -0.0963 0.5355 0.8378 0.205 Uiso 1 1 calc R
C9 C 0.1617(5) 0.25341(19) 0.4377(5) 0.1144(14) Uani 1 1 d .
H9A H 0.0825 0.2543 0.3631 0.172 Uiso 1 1 calc R
H9B H 0.1330 0.2232 0.5083 0.172 Uiso 1 1 calc R
H9C H 0.2547 0.2376 0.4046 0.172 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C15 N1 C12 121.3(2)
C2 C1 C6 118.6(3)
C2 C1 C8 121.8(3)
C6 C1 C8 119.6(3)
N1 C12 C13 116.8(3)
N1 C12 C11 120.4(2)
C13 C12 C11 114.9(2)
N1 C12 C10 117.4(2)
C13 C12 C10 116.1(2)
C11 C12 C10 58.70(19)
O5 C15 N1 121.0(3)
O5 C15 C16 122.3(3)
N1 C15 C16 116.7(2)
C6 C5 C4 121.2(3)
C13 O3 C14 114.5(3)
C8 O2 C9 116.8(3)
C11 C10 C4 122.3(2)
C11 C10 C17 116.4(3)
C4 C10 C17 112.8(2)
C11 C10 C12 59.8(2)
C4 C10 C12 118.0(2)
C17 C10 C12 118.1(2)
C2 C3 C4 120.6(3)
C5 C4 C3 118.3(3)
C5 C4 C10 123.1(3)
C3 C4 C10 118.5(2)
O1 C8 O2 124.3(3)
O1 C8 C1 123.1(3)
O2 C8 C1 112.6(3)
O4 C13 O3 124.2(3)
O4 C13 C12 123.6(3)
O3 C13 C12 112.2(3)
C3 C2 C1 120.4(3)
C5 C6 C1 121.0(3)
C10 C11 C12 61.52(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C15 1.340(4)
N1 C12 1.426(3)
C1 C2 1.383(4)
C1 C6 1.386(4)
C1 C8 1.485(4)
O5 C15 1.230(3)
C12 C13 1.496(4)
C12 C11 1.502(4)
C12 C10 1.528(4)
C15 C16 1.487(4)
C5 C6 1.364(4)
C5 C4 1.376(4)
O3 C13 1.332(4)
O3 C14 1.462(5)
O2 C8 1.323(4)
O2 C9 1.443(4)
C10 C11 1.485(4)
C10 C4 1.501(4)
C10 C17 1.519(4)
C3 C2 1.381(4)
C3 C4 1.395(4)
O4 C13 1.195(4)
C8 O1 1.204(4)
