#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/66/4026608.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_4026608
loop_
_publ_author_name
'Goutam Kumar Kole'
'Geok Kheng Tan'
'Jagadese J. Vittal'
_publ_contact_author
; 
     Dr. Jagadese J. Vittal
     Department of Chemistry
     National University of Singapore
     3 Science Drive 3
     SINGAPORE 117543 
;
_publ_contact_author_email       chmjjv@nus.edu.sg
_publ_contact_author_fax         '(65) 6779 1691'
_publ_contact_author_phone       '(65) 6516 2677'
_publ_section_title
;
 Role of Anions in the Synthesis of Cyclobutane Derivatives via [2 + 2]
 Cycloaddition Reaction in the Solid State and Their Isomerization in
 Solution
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7860
_journal_page_last               7865
_journal_paper_doi               10.1021/jo201268p
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C8 H8 Cl N O6'
_chemical_formula_weight         249.60
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.6250(10)
_cell_angle_beta                 100.4850(10)
_cell_angle_gamma                95.5600(10)
_cell_formula_units_Z            2
_cell_length_a                   5.0430(3)
_cell_length_b                   8.4238(6)
_cell_length_c                   12.5243(9)
_cell_measurement_reflns_used    4724
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.54
_cell_volume                     497.81(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6455
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_T_max  0.9765
_exptl_absorpt_correction_T_min  0.7850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2283
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0544P)²+0.1967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0952
_reflns_number_gt                2188
_reflns_number_total             2283
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201268p_si_002_3.cif
_cod_data_source_block           compound2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4026608
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
O1 O 0.1265(3) 0.01270(14) 0.38652(10) 0.0404(3) Uani 1 1 d .
H1 H -0.0091 -0.0260 0.3336 0.061 Uiso 1 1 calc R
O2 O -0.0704(3) 0.24231(15) 0.41135(11) 0.0447(3) Uani 1 1 d .
N1 N 0.9884(3) 0.67347(16) 0.87700(11) 0.0300(3) Uani 1 1 d .
H1N H 1.101(5) 0.723(3) 0.938(2) 0.052(6) Uiso 1 1 d .
C1 C 0.1138(3) 0.17094(18) 0.43864(12) 0.0277(3) Uani 1 1 d .
C2 C 0.3522(3) 0.24724(18) 0.53380(12) 0.0276(3) Uani 1 1 d .
H2 H 0.4845 0.1825 0.5531 0.033 Uiso 1 1 calc R
C3 C 0.3789(3) 0.40673(17) 0.59162(11) 0.0253(3) Uani 1 1 d .
H3 H 0.2451 0.4676 0.5678 0.030 Uiso 1 1 calc R
C4 C 1.0002(3) 0.51224(19) 0.83028(13) 0.0309(3) Uani 1 1 d .
H4 H 1.1399 0.4617 0.8621 0.037 Uiso 1 1 calc R
C5 C 0.8078(3) 0.42095(17) 0.73577(13) 0.0287(3) Uani 1 1 d .
H5 H 0.8160 0.3079 0.7021 0.034 Uiso 1 1 calc R
C6 C 0.5992(3) 0.49696(16) 0.68965(11) 0.0228(3) Uani 1 1 d .
C7 C 0.5970(3) 0.66567(17) 0.74159(12) 0.0264(3) Uani 1 1 d .
H7 H 0.4603 0.7202 0.7120 0.032 Uiso 1 1 calc R
C8 C 0.7949(3) 0.75199(18) 0.83612(13) 0.0294(3) Uani 1 1 d .
H8 H 0.7938 0.8654 0.8716 0.035 Uiso 1 1 calc R
Cl1 Cl 1.56147(6) 0.84580(4) 1.12258(3) 0.02521(13) Uani 1 1 d .
O3 O 1.7008(3) 0.99503(16) 1.11279(13) 0.0485(3) Uani 1 1 d .
O4 O 1.6793(2) 0.82022(15) 1.22920(9) 0.0380(3) Uani 1 1 d .
O5 O 1.5829(3) 0.70382(17) 1.03238(11) 0.0507(3) Uani 1 1 d .
O6 O 1.2761(2) 0.85672(16) 1.11528(12) 0.0414(3) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0410(7) 0.0276(6) 0.0356(6) -0.0041(5) -0.0143(5) 0.0066(5)
O2 0.0399(7) 0.0342(6) 0.0446(7) 0.0012(5) -0.0161(5) 0.0104(5)
N1 0.0254(6) 0.0274(6) 0.0283(6) 0.0035(5) -0.0063(5) -0.0016(5)
C1 0.0277(7) 0.0252(7) 0.0246(7) 0.0040(5) -0.0024(5) 0.0023(5)
C2 0.0257(7) 0.0262(7) 0.0264(7) 0.0059(5) -0.0030(5) 0.0044(5)
C3 0.0228(6) 0.0256(7) 0.0240(6) 0.0065(5) -0.0020(5) 0.0023(5)
C4 0.0250(7) 0.0281(7) 0.0356(8) 0.0103(6) -0.0046(6) 0.0037(5)
C5 0.0272(7) 0.0209(6) 0.0332(7) 0.0049(5) -0.0011(6) 0.0037(5)
C6 0.0219(6) 0.0219(6) 0.0221(6) 0.0059(5) 0.0010(5) 0.0008(5)
C7 0.0254(6) 0.0226(6) 0.0288(7) 0.0073(5) -0.0002(5) 0.0048(5)
C8 0.0289(7) 0.0210(6) 0.0321(7) 0.0025(5) -0.0002(6) 0.0015(5)
Cl1 0.02252(19) 0.02350(19) 0.02548(19) 0.00732(13) -0.00374(12) 0.00042(12)
O3 0.0373(7) 0.0429(7) 0.0650(9) 0.0324(6) -0.0062(6) -0.0096(5)
O4 0.0392(6) 0.0396(6) 0.0284(6) 0.0132(5) -0.0100(5) -0.0029(5)
O5 0.0600(8) 0.0469(8) 0.0349(7) -0.0030(6) 0.0049(6) 0.0129(6)
O6 0.0244(6) 0.0436(7) 0.0553(7) 0.0176(6) 0.0012(5) 0.0066(5)
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
C8 N1 C4 122.96(13)
O2 C1 O1 123.61(13)
O2 C1 C2 124.46(13)
O1 C1 C2 111.93(12)
C3 C2 C1 119.94(13)
C2 C3 C6 125.76(13)
N1 C4 C5 119.76(13)
C4 C5 C6 119.66(13)
C7 C6 C5 118.21(12)
C7 C6 C3 118.61(12)
C5 C6 C3 123.16(12)
C8 C7 C6 119.96(13)
N1 C8 C7 119.45(13)
O3 Cl1 O5 110.93(9)
O3 Cl1 O6 110.01(8)
O5 Cl1 O6 107.62(8)
O3 Cl1 O4 109.68(7)
O5 Cl1 O4 108.48(8)
O6 Cl1 O4 110.09(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3305(17)
O2 C1 1.2018(18)
N1 C8 1.3330(19)
N1 C4 1.338(2)
C1 C2 1.4818(19)
C2 C3 1.324(2)
C3 C6 1.4686(18)
C4 C5 1.372(2)
C5 C6 1.3994(19)
C6 C7 1.3967(19)
C7 C8 1.376(2)
Cl1 O3 1.4256(12)
Cl1 O5 1.4353(13)
Cl1 O6 1.4388(12)
Cl1 O4 1.4400(11)
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
O1 H1 O4 0.83 1.95 2.7478(15) 160.9 1_344
N1 H1N O6 0.84(3) 2.18(3) 2.9837(19) 162(2) .
N1 H1N O5 0.84(3) 2.54(2) 3.2095(19) 137(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659406
