#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:36:15 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178474 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/95/4029548.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_4029548
loop_
_publ_author_name
'Avery, Thomas D.'
'Greatrex, Ben W.'
'Pedersen, Daniel Sejer'
'Taylor, Dennis K.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 A concise route to beta-Cyclopropyl amino acids utilizing 1,2-dioxines
 and stabilized phosphonate nucleophiles.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2633
_journal_page_last               2640
_journal_paper_doi               10.1021/jo7024256
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C12 H14 N O4, Cl'
_chemical_formula_sum            'C12 H14 Cl N O4'
_chemical_formula_weight         271.69
_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
_cell_angle_beta                 94.453(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9985(13)
_cell_length_b                   7.1946(9)
_cell_length_c                   17.939(3)
_cell_measurement_reflns_used    6399
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      30.3
_cell_measurement_theta_min      2.3
_cell_volume                     1286.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SHELXTL (Bruker, 2000)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      98(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker AXS SMART CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_av_sigmaI/netI    0.015
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12263
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.51
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.08
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2659
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_all          0.037
_refine_ls_R_factor_gt           0.035
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0462P)²+0.9132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.091
_refine_ls_wR_factor_ref         0.092
_reflns_number_gt                2567
_reflns_number_total             2659
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo7024256-file007.cif
_cod_data_source_block           6
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4029548
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
Cl1 Cl 0.35498(4) 0.79627(5) 0.563317(18) 0.01730(12) Uani 1 1 d .
O1 O 0.52091(11) 1.27119(16) 0.73491(6) 0.0232(3) Uani 1 1 d .
O2 O 0.70831(11) 1.12823(15) 0.78326(6) 0.0202(2) Uani 1 1 d D
H2O H 0.6886 1.1805 0.8228 0.030 Uiso 1 1 d D
O3 O 0.67327(11) 0.51086(14) 0.60461(6) 0.0205(2) Uani 1 1 d .
O4 O 0.65524(11) 0.60792(14) 0.48528(6) 0.0183(2) Uani 1 1 d D
H4O H 0.6433 0.4939 0.4771 0.027 Uiso 1 1 d D
N1 N 0.54068(12) 1.14954(17) 0.59856(7) 0.0163(3) Uani 1 1 d .
H1A H 0.5204 1.2726 0.6010 0.024 Uiso 1 1 calc R
H1B H 0.4687 1.0810 0.6101 0.024 Uiso 1 1 calc R
H1C H 0.5618 1.1208 0.5515 0.024 Uiso 1 1 calc R
C1 C 0.69461(14) 0.9041(2) 0.65071(8) 0.0141(3) Uani 1 1 d .
H1 H 0.6417 0.8200 0.6817 0.017 Uiso 1 1 calc R
C2 C 0.73139(14) 0.8237(2) 0.57634(8) 0.0143(3) Uani 1 1 d .
H2 H 0.7360 0.9119 0.5336 0.017 Uiso 1 1 calc R
C3 C 0.83736(14) 0.8437(2) 0.64168(8) 0.0154(3) Uani 1 1 d .
H3 H 0.8617 0.7233 0.6671 0.019 Uiso 1 1 calc R
C4 C 0.65756(14) 1.1073(2) 0.65290(8) 0.0142(3) Uani 1 1 d .
H4 H 0.7360 1.1816 0.6385 0.017 Uiso 1 1 calc R
C5 C 0.61931(15) 1.1766(2) 0.72878(8) 0.0156(3) Uani 1 1 d .
C6 C 0.68391(14) 0.6325(2) 0.55869(8) 0.0151(3) Uani 1 1 d .
C7 C 0.95183(14) 0.9751(2) 0.64037(8) 0.0170(3) Uani 1 1 d .
C8 C 0.95998(16) 1.1167(2) 0.58769(9) 0.0209(3) Uani 1 1 d .
H8 H 0.8907 1.1311 0.5488 0.025 Uiso 1 1 calc R
C9 C 1.06970(17) 1.2370(2) 0.59210(10) 0.0252(4) Uani 1 1 d .
H9 H 1.0737 1.3349 0.5568 0.030 Uiso 1 1 calc R
C10 C 1.17267(17) 1.2148(2) 0.64742(10) 0.0249(4) Uani 1 1 d .
H10 H 1.2469 1.2976 0.6503 0.030 Uiso 1 1 calc R
C11 C 1.16737(16) 1.0718(2) 0.69860(9) 0.0238(3) Uani 1 1 d .
H11 H 1.2392 1.0545 0.7358 0.029 Uiso 1 1 calc R
C12 C 1.05719(15) 0.9533(2) 0.69573(9) 0.0203(3) Uani 1 1 d .
H12 H 1.0534 0.8567 0.7316 0.024 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
C5 O2 H2O 108.6
C6 O4 H4O 108.5
C4 N1 H1A 109.5
C4 N1 H1B 109.5
H1A N1 H1B 109.5
C4 N1 H1C 109.5
H1A N1 H1C 109.5
H1B N1 H1C 109.5
C4 C1 C3 121.09(12)
C4 C1 C2 117.81(12)
C3 C1 C2 60.25(9)
C4 C1 H1 115.5
C3 C1 H1 115.5
C2 C1 H1 115.5
C6 C2 C3 116.39(12)
C6 C2 C1 116.37(12)
C3 C2 C1 59.46(9)
C6 C2 H2 117.3
C3 C2 H2 117.3
C1 C2 H2 117.3
C7 C3 C1 123.61(13)
C7 C3 C2 122.56(12)
C1 C3 C2 60.29(9)
C7 C3 H3 113.5
C1 C3 H3 113.5
C2 C3 H3 113.5
N1 C4 C1 111.19(11)
N1 C4 C5 106.14(11)
C1 C4 C5 114.76(12)
N1 C4 H4 108.2
C1 C4 H4 108.2
C5 C4 H4 108.2
O1 C5 O2 126.13(13)
O1 C5 C4 121.83(13)
O2 C5 C4 111.97(12)
O3 C6 O4 123.38(13)
O3 C6 C2 124.66(13)
O4 C6 C2 111.96(12)
C8 C7 C12 118.82(14)
C8 C7 C3 124.08(14)
C12 C7 C3 117.11(14)
C9 C8 C7 120.08(15)
C9 C8 H8 120.0
C7 C8 H8 120.0
C10 C9 C8 120.50(16)
C10 C9 H9 119.7
C8 C9 H9 119.7
C11 C10 C9 119.86(15)
C11 C10 H10 120.1
C9 C10 H10 120.1
C10 C11 C12 120.18(15)
C10 C11 H11 119.9
C12 C11 H11 119.9
C11 C12 C7 120.52(15)
C11 C12 H12 119.7
C7 C12 H12 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.2084(19)
O2 C5 1.3164(18)
O2 H2O 0.8400
O3 C6 1.2122(18)
O4 C6 1.3375(18)
O4 H4O 0.8399
N1 C4 1.4939(18)
N1 H1A 0.9100
N1 H1B 0.9100
N1 H1C 0.9100
C1 C4 1.509(2)
C1 C3 1.5125(19)
C1 C2 1.5253(19)
C1 H1 1.0000
C2 C6 1.481(2)
C2 C3 1.525(2)
C2 H2 1.0000
C3 C7 1.486(2)
C3 H3 1.0000
C4 C5 1.5260(19)
C4 H4 1.0000
C7 C8 1.396(2)
C7 C12 1.399(2)
C8 C9 1.395(2)
C8 H8 0.9500
C9 C10 1.383(3)
C9 H9 0.9500
C10 C11 1.382(3)
C10 H10 0.9500
C11 C12 1.391(2)
C11 H11 0.9500
C12 H12 0.9500
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
C4 C1 C2 C6 -141.76(13)
C3 C1 C2 C6 106.47(14)
C4 C1 C2 C3 111.77(14)
C4 C1 C3 C7 5.0(2)
C2 C1 C3 C7 111.39(15)
C4 C1 C3 C2 -106.43(14)
C6 C2 C3 C7 140.49(13)
C1 C2 C3 C7 -113.06(15)
C6 C2 C3 C1 -106.44(14)
C3 C1 C4 N1 128.66(13)
C2 C1 C4 N1 58.36(16)
C3 C1 C4 C5 -110.87(14)
C2 C1 C4 C5 178.83(12)
N1 C4 C5 O1 -10.20(19)
C1 C4 C5 O1 -133.42(15)
N1 C4 C5 O2 172.76(12)
C1 C4 C5 O2 49.55(17)
C3 C2 C6 O3 33.5(2)
C1 C2 C6 O3 -33.7(2)
C3 C2 C6 O4 -145.70(12)
C1 C2 C6 O4 147.08(12)
C1 C3 C7 C8 -60.3(2)
C2 C3 C7 C8 13.3(2)
C1 C3 C7 C12 119.81(15)
C2 C3 C7 C12 -166.55(13)
C12 C7 C8 C9 -2.0(2)
C3 C7 C8 C9 178.14(14)
C7 C8 C9 C10 1.5(2)
C8 C9 C10 C11 0.3(2)
C9 C10 C11 C12 -1.6(2)
C10 C11 C12 C7 1.1(2)
C8 C7 C12 C11 0.7(2)
C3 C7 C12 C11 -179.45(13)
