#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/73/1507317.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_1507317
loop_
_publ_author_name
'Shi, Weifeng'
'Jiang, Nan'
'Zhang, Shiwei'
'Wu, Weiming'
'Du, Daming'
'Wang, Jianbo'
_publ_section_title
;
 Unusual reaction of beta-hydroxy alpha-diazo carbonyl compounds with
 Cl3CCN/NaH and Rh(II)-catalyzed reaction of beta-trichloroacetylamino
 alpha-diazo carbonyl compounds.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2243
_journal_page_last               2246
_journal_paper_doi               10.1021/ol034550o
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C9 H12 Cl3 N3 O3'
_chemical_formula_weight         316.57
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens
'hydrogen atoms are generated by HFIX instructions''
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.51(3)
_cell_angle_beta                 71.86(3)
_cell_angle_gamma                78.36(3)
_cell_formula_units_Z            4
_cell_length_a                   9.6616(19)
_cell_length_b                   10.436(2)
_cell_length_c                   15.210(3)
_cell_measurement_reflns_used    13008
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.27
_cell_volume                     1425.0(6)
_computing_cell_refinement
'Molecular Structure Corporation (1994) MSC/AFC Diffractometer Control Software MSC, 3200 Research Forest Drive, The Woodlands, TX 77381 USA.''
_computing_data_collection
'Molecular Structure Corporation (1994) MSC/AFC Diffractometer Control Software MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.''
_computing_data_reduction
'Sheldrick, G. M. (1997) SHELXS97, Program for the Solution of Crystal Structure, University of Gottingen, Germany.''
_computing_molecular_graphics
'Interactive Molecular Graphics XP, Virsion 4.2 for MSDOS (1990), Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.''
_computing_publication_material
'Sheldrick, G. M. (1997) SHELXL97, Program for the refinement of Crystal Structure, University of Gottingen, Germany.''
_computing_structure_refinement
'Sheldrick, G. M. (1997) SHELXL97, Program for the Refinement of Crystal Structure, University of Gottingen, Germany.''
_computing_structure_solution
'Sheldrick, G. M. (1997) SHELXS97, Program for the Solution of Crystal Structure, University of Gottingen, Germany.''
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean '100x100 microns'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       Oscillation
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6410
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  0.798
_exptl_absorpt_correction_T_min  0.608
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment
'hydrogen coordinates ride on the coordinates of the previous atom, the isotropic U values are 1.2 OR 1.5 time over the U values of the previous atom.''
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         6410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0591
_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)+(0.0776P)²+0.5844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1663
_refine_ls_wR_factor_ref         0.1786
_reflns_number_gt                3811
_reflns_number_total             6410
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol034550osi20030329_110605.cif
_cod_data_source_block           7b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1425.0(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1507317
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cl1 Cl -0.54106(12) 1.46533(12) 0.31875(8) 0.0844(4) Uani 1 1 d .
Cl2 Cl -0.71170(14) 1.64671(10) 0.22842(8) 0.0826(3) Uani 1 1 d .
Cl3 Cl -0.85899(13) 1.51226(14) 0.38204(8) 0.0914(4) Uani 1 1 d .
Cl4 Cl 0.48509(13) 1.09219(14) 0.32619(11) 0.1026(5) Uani 1 1 d .
Cl5 Cl 0.39364(13) 0.86073(15) 0.40866(8) 0.1049(5) Uani 1 1 d .
Cl6 Cl 0.58234(11) 0.84645(12) 0.22065(8) 0.0805(3) Uani 1 1 d .
O1 O -0.7827(3) 1.3120(3) 0.2407(2) 0.0828(8) Uani 1 1 d .
O2 O -0.6297(3) 1.4678(3) -0.0555(2) 0.0904(9) Uani 1 1 d .
O3 O -0.8146(3) 1.3769(2) -0.06904(17) 0.0643(6) Uani 1 1 d .
O4 O 0.3081(3) 0.9631(3) 0.19179(17) 0.0719(7) Uani 1 1 d .
O5 O -0.1036(3) 0.9181(3) 0.46226(17) 0.0670(7) Uani 1 1 d .
O6 O -0.1598(3) 0.7943(2) 0.36372(15) 0.0548(6) Uani 1 1 d .
N1 N -0.5857(3) 1.3723(3) 0.1370(2) 0.0638(8) Uani 1 1 d .
N2 N -0.7719(5) 1.2013(4) 0.0440(3) 0.0825(11) Uani 1 1 d .
N3 N -0.8524(7) 1.1348(5) 0.0604(4) 0.1259(19) Uani 1 1 d .
N4 N 0.1693(3) 1.0329(3) 0.33768(18) 0.0500(6) Uani 1 1 d .
N5 N -0.0403(4) 0.9271(3) 0.2251(2) 0.0635(8) Uani 1 1 d .
N6 N -0.0375(5) 0.8953(4) 0.1544(3) 0.0991(13) Uani 1 1 d .
C1 C -0.7026(4) 1.4975(3) 0.2838(2) 0.0543(8) Uani 1 1 d .
C2 C -0.6944(4) 1.3833(3) 0.2172(3) 0.0543(8) Uani 1 1 d .
C3 C -0.5597(6) 1.2620(6) 0.0710(4) 0.1088(19) Uani 1 1 d .
H3 H -0.5877 1.1928 0.1127 0.131 Uiso 1 1 calc R
C4 C -0.6771(5) 1.2809(4) 0.0236(3) 0.0712(11) Uani 1 1 d .
C5 C -0.7017(4) 1.3834(4) -0.0366(3) 0.0641(9) Uani 1 1 d .
C6 C -0.4169(7) 1.2083(7) 0.0233(5) 0.143(3) Uani 1 1 d .
H6A H -0.3832 1.2671 -0.0247 0.172 Uiso 1 1 calc R
H6B H -0.4173 1.1278 -0.0079 0.172 Uiso 1 1 calc R
C7 C -0.3004(5) 1.1760(5) 0.0700(4) 0.0982(15) Uani 1 1 d .
H7A H -0.2050 1.1448 0.0243 0.147 Uiso 1 1 calc R
H7B H -0.3233 1.1092 0.1127 0.147 Uiso 1 1 calc R
H7C H -0.2978 1.2531 0.1029 0.147 Uiso 1 1 calc R
C8 C -0.8530(5) 1.4816(4) -0.1253(3) 0.0786(11) Uani 1 1 d .
H8A H -0.7676 1.4862 -0.1788 0.094 Uiso 1 1 calc R
H8B H -0.8848 1.5650 -0.0897 0.094 Uiso 1 1 calc R
C9 C -0.9760(5) 1.4522(5) -0.1554(3) 0.0878(13) Uani 1 1 d .
H9A H -1.0040 1.5193 -0.1938 0.132 Uiso 1 1 calc R
H9B H -1.0602 1.4491 -0.1019 0.132 Uiso 1 1 calc R
H9C H -0.9435 1.3690 -0.1898 0.132 Uiso 1 1 calc R
C10 C 0.4333(4) 0.9457(4) 0.3057(2) 0.0612(9) Uani 1 1 d .
C11 C 0.2951(4) 0.9812(3) 0.2730(2) 0.0507(8) Uani 1 1 d .
C12 C 0.0329(3) 1.0790(3) 0.3128(2) 0.0511(8) Uani 1 1 d .
H12 H 0.0620 1.1134 0.2510 0.061 Uiso 1 1 calc R
C13 C -0.0393(4) 0.9642(3) 0.3066(2) 0.0502(8) Uani 1 1 d .
C14 C -0.1021(3) 0.8930(3) 0.3842(2) 0.0489(7) Uani 1 1 d .
C15 C -0.0685(4) 1.1901(3) 0.3797(3) 0.0647(10) Uani 1 1 d .
H15A H -0.0149 1.2593 0.3799 0.078 Uiso 1 1 calc R
H15B H -0.0966 1.1589 0.4417 0.078 Uiso 1 1 calc R
C16 C -0.2083(5) 1.2456(4) 0.3545(4) 0.0971(16) Uani 1 1 d .
H16A H -0.2701 1.3149 0.3991 0.146 Uiso 1 1 calc R
H16B H -0.2620 1.1775 0.3546 0.146 Uiso 1 1 calc R
H16C H -0.1811 1.2793 0.2940 0.146 Uiso 1 1 calc R
C17 C -0.2344(4) 0.7257(3) 0.4422(2) 0.0603(9) Uani 1 1 d .
H17A H -0.3250 0.7829 0.4807 0.072 Uiso 1 1 calc R
H17B H -0.1700 0.6981 0.4797 0.072 Uiso 1 1 calc R
C18 C -0.2703(5) 0.6095(4) 0.4049(3) 0.0714(11) Uani 1 1 d .
H18A H -0.3191 0.5618 0.4554 0.107 Uiso 1 1 calc R
H18B H -0.1800 0.5538 0.3668 0.107 Uiso 1 1 calc R
H18C H -0.3349 0.6380 0.3686 0.107 Uiso 1 1 calc R
HN1 H -0.5227 1.4409 0.1186 0.084(13) Uiso 1 1 d R
HN4 H 0.1620 1.0466 0.4010 0.058(10) Uiso 1 1 d 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 O3 C8 116.4(3)
C14 O6 C17 115.8(3)
C2 N1 C3 119.7(4)
N3 N2 C4 179.3(5)
C11 N4 C12 120.0(3)
N6 N5 C13 178.3(4)
C2 C1 Cl3 110.8(2)
C2 C1 Cl2 110.7(2)
Cl3 C1 Cl2 108.75(19)
C2 C1 Cl1 108.7(2)
Cl3 C1 Cl1 108.75(19)
Cl2 C1 Cl1 109.18(19)
O1 C2 N1 125.5(4)
O1 C2 C1 119.8(3)
N1 C2 C1 114.7(3)
C6 C3 N1 117.0(5)
C6 C3 C4 120.3(5)
N1 C3 C4 111.0(4)
N2 C4 C5 117.1(4)
N2 C4 C3 117.2(5)
C5 C4 C3 125.6(4)
O2 C5 O3 123.4(4)
O2 C5 C4 123.7(4)
O3 C5 C4 113.0(4)
C3 C6 C7 121.7(6)
O3 C8 C9 106.9(4)
C11 C10 Cl6 110.8(2)
C11 C10 Cl4 108.1(3)
Cl6 C10 Cl4 109.0(2)
C11 C10 Cl5 110.8(2)
Cl6 C10 Cl5 108.5(2)
Cl4 C10 Cl5 109.5(2)
O4 C11 N4 124.7(3)
O4 C11 C10 119.7(3)
N4 C11 C10 115.6(3)
N4 C12 C15 110.0(3)
N4 C12 C13 109.7(3)
C15 C12 C13 113.9(3)
N5 C13 C14 118.4(3)
N5 C13 C12 117.8(3)
C14 C13 C12 123.8(3)
O5 C14 O6 122.3(3)
O5 C14 C13 123.3(3)
O6 C14 C13 114.4(3)
C12 C15 C16 112.1(3)
O6 C17 C18 107.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.770(3)
Cl2 C1 1.764(4)
Cl3 C1 1.744(4)
Cl4 C10 1.761(4)
Cl5 C10 1.768(4)
Cl6 C10 1.755(4)
O1 C2 1.214(4)
O2 C5 1.209(5)
O3 C5 1.342(4)
O3 C8 1.443(5)
O4 C11 1.215(4)
O5 C14 1.213(4)
O6 C14 1.347(4)
O6 C17 1.455(4)
N1 C2 1.326(5)
N1 C3 1.464(5)
N2 N3 1.115(6)
N2 C4 1.322(6)
N4 C11 1.318(4)
N4 C12 1.471(4)
N5 N6 1.119(4)
N5 C13 1.305(4)
C1 C2 1.544(5)
C3 C6 1.348(7)
C3 C4 1.504(6)
C4 C5 1.435(6)
C6 C7 1.491(7)
C8 C9 1.485(6)
C10 C11 1.542(5)
C12 C15 1.511(5)
C12 C13 1.520(4)
C13 C14 1.425(5)
C15 C16 1.520(5)
C17 C18 1.489(5)
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
N1 HN1 O2 1.01 1.91 2.900(5) 163.2 2_485
N4 HN4 O5 0.95 1.99 2.935(4) 168.7 2_576
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
C3 N1 C2 O1 -4.0(6)
C3 N1 C2 C1 175.4(3)
Cl3 C1 C2 O1 -6.1(4)
Cl2 C1 C2 O1 -126.8(3)
Cl1 C1 C2 O1 113.3(3)
Cl3 C1 C2 N1 174.5(2)
Cl2 C1 C2 N1 53.8(4)
Cl1 C1 C2 N1 -66.1(3)
C2 N1 C3 C6 -142.0(6)
C2 N1 C3 C4 74.8(6)
N3 N2 C4 C5 15(53)
N3 N2 C4 C3 -170(100)
C6 C3 C4 N2 106.9(7)
N1 C3 C4 N2 -111.3(5)
C6 C3 C4 C5 -77.8(7)
N1 C3 C4 C5 64.1(6)
C8 O3 C5 O2 -3.1(5)
C8 O3 C5 C4 176.0(3)
N2 C4 C5 O2 174.7(4)
C3 C4 C5 O2 -0.6(6)
N2 C4 C5 O3 -4.4(5)
C3 C4 C5 O3 -179.8(4)
N1 C3 C6 C7 46.4(10)
C4 C3 C6 C7 -173.9(6)
C5 O3 C8 C9 178.3(3)
C12 N4 C11 O4 -2.8(5)
C12 N4 C11 C10 175.7(3)
Cl6 C10 C11 O4 -14.4(4)
Cl4 C10 C11 O4 105.1(3)
Cl5 C10 C11 O4 -134.9(3)
Cl6 C10 C11 N4 167.1(2)
Cl4 C10 C11 N4 -73.5(3)
Cl5 C10 C11 N4 46.6(4)
C11 N4 C12 C15 -151.0(3)
C11 N4 C12 C13 83.0(4)
N6 N5 C13 C14 -128(14)
N6 N5 C13 C12 50(15)
N4 C12 C13 N5 -112.1(3)
C15 C12 C13 N5 124.1(4)
N4 C12 C13 C14 66.1(4)
C15 C12 C13 C14 -57.6(4)
C17 O6 C14 O5 4.5(5)
C17 O6 C14 C13 -175.7(3)
N5 C13 C14 O5 178.4(3)
C12 C13 C14 O5 0.1(5)
N5 C13 C14 O6 -1.4(4)
C12 C13 C14 O6 -179.6(3)
N4 C12 C15 C16 177.5(3)
C13 C12 C15 C16 -58.9(4)
C14 O6 C17 C18 -171.9(3)
