#------------------------------------------------------------------------------
#$Date: 2017-03-27 21:27:41 +0300 (Mon, 27 Mar 2017) $
#$Revision: 194547 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/27/1542744.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_1542744
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            'C14 H17 N O3'
_chemical_formula_weight         247.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.1055(2)
_cell_length_b                   9.4967(2)
_cell_length_c                   30.8939(7)
_cell_measurement_reflns_used    2765
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.8030
_cell_measurement_theta_min      4.2770
_cell_volume                     2671.46(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            5971
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  0.9328
_exptl_absorpt_correction_T_min  0.8718
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0492
_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)+(0.0906P)²+1.8495P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1457
_reflns_number_gt                2028
_reflns_number_total             2358
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00416_si_003.cif
_cod_data_source_block           zcl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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.

2017-03-19
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C18.67 H22.67 N1.33 O4'
_cod_original_formula_weight         329.71
_cod_original_formula_units_Z            6
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1542744
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.21915(15) 0.35720(13) 0.32968(4) 0.0316(3) Uani 1 1 d .
O3 O 0.64118(16) 0.36603(15) 0.31833(4) 0.0358(4) Uani 1 1 d .
N1 N 0.32217(17) 0.56233(17) 0.35033(5) 0.0248(4) Uani 1 1 d .
O2 O 0.51452(18) 0.53102(17) 0.28231(5) 0.0441(4) Uani 1 1 d .
C10 C 0.21001(19) 0.48551(18) 0.33443(5) 0.0239(4) Uani 1 1 d .
C11 C 0.0733(2) 0.5657(2) 0.32335(7) 0.0309(4) Uani 1 1 d .
H11A H 0.0007 0.5020 0.3122 0.046 Uiso 1 1 calc R
H11B H 0.0956 0.6355 0.3019 0.046 Uiso 1 1 calc R
H11C H 0.0361 0.6110 0.3489 0.046 Uiso 1 1 calc R
C9 C 0.46244(19) 0.49838(18) 0.35701(6) 0.0255(4) Uani 1 1 d .
C12 C 0.5407(2) 0.4683(2) 0.31523(6) 0.0287(4) Uani 1 1 d .
C8 C 0.4794(2) 0.4029(2) 0.39564(6) 0.0300(4) Uani 1 1 d .
H8A H 0.3933 0.3861 0.4134 0.036 Uiso 1 1 calc R
H8B H 0.5447 0.3227 0.3928 0.036 Uiso 1 1 calc R
C14 C 0.7137(2) 0.5598(3) 0.39463(7) 0.0403(5) Uani 1 1 d .
H14A H 0.7516 0.5899 0.4221 0.060 Uiso 1 1 calc R
H14B H 0.7386 0.6280 0.3729 0.060 Uiso 1 1 calc R
H14C H 0.7557 0.4704 0.3871 0.060 Uiso 1 1 calc R
C7 C 0.5474(2) 0.5459(2) 0.39743(6) 0.0283(4) Uani 1 1 d .
C4 C 0.3711(3) 0.8677(2) 0.47978(7) 0.0425(5) Uani 1 1 d .
H4A H 0.3367 0.9380 0.4981 0.051 Uiso 1 1 calc R
C5 C 0.4342(2) 0.9025(2) 0.44065(7) 0.0394(5) Uani 1 1 d .
H5A H 0.4407 0.9964 0.4323 0.047 Uiso 1 1 calc R
C6 C 0.4878(2) 0.7979(2) 0.41373(7) 0.0338(5) Uani 1 1 d .
H6A H 0.5306 0.8224 0.3875 0.041 Uiso 1 1 calc R
C1 C 0.4786(2) 0.6573(2) 0.42538(6) 0.0286(4) Uani 1 1 d .
C2 C 0.4128(3) 0.6235(2) 0.46454(7) 0.0391(5) Uani 1 1 d .
H2A H 0.4045 0.5297 0.4728 0.047 Uiso 1 1 calc R
C3 C 0.3593(3) 0.7284(3) 0.49161(7) 0.0469(6) Uani 1 1 d .
H3A H 0.3153 0.7045 0.5178 0.056 Uiso 1 1 calc R
C13 C 0.7184(3) 0.3328(3) 0.27836(8) 0.0479(6) Uani 1 1 d .
H13A H 0.7876 0.2585 0.2836 0.072 Uiso 1 1 calc R
H13B H 0.7695 0.4149 0.2683 0.072 Uiso 1 1 calc R
H13C H 0.6489 0.3030 0.2568 0.072 Uiso 1 1 calc R
H1 H 0.316(2) 0.650(2) 0.3478(7) 0.023(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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C12 O3 C13 115.27(16)
C10 N1 C9 119.98(15)
O1 C10 N1 121.90(17)
O1 C10 C11 122.16(17)
N1 C10 C11 115.94(15)
N1 C9 C12 112.39(15)
N1 C9 C8 117.51(16)
C12 C9 C8 121.16(16)
N1 C9 C7 116.27(15)
C12 C9 C7 120.99(15)
C8 C9 C7 58.79(12)
O2 C12 O3 123.78(18)
O2 C12 C9 122.58(17)
O3 C12 C9 113.64(16)
C7 C8 C9 61.61(12)
C8 C7 C1 119.23(16)
C8 C7 C14 119.28(17)
C1 C7 C14 112.75(16)
C8 C7 C9 59.60(12)
C1 C7 C9 117.63(15)
C14 C7 C9 118.70(16)
C5 C4 C3 119.7(2)
C4 C5 C6 120.1(2)
C5 C6 C1 121.0(2)
C2 C1 C6 118.36(19)
C2 C1 C7 121.26(18)
C6 C1 C7 120.26(18)
C1 C2 C3 120.7(2)
C4 C3 C2 120.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C10 1.230(2)
O3 C12 1.338(2)
O3 C13 1.456(2)
N1 C10 1.348(2)
N1 C9 1.429(2)
O2 C12 1.202(2)
C10 C11 1.499(3)
C9 C12 1.502(3)
C9 C8 1.507(3)
C9 C7 1.537(3)
C8 C7 1.494(3)
C14 C7 1.522(3)
C7 C1 1.502(3)
C4 C5 1.379(3)
C4 C3 1.376(3)
C5 C6 1.384(3)
C6 C1 1.386(3)
C1 C2 1.388(3)
C2 C3 1.389(3)
