#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:18:00 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179446 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/43/4334333.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_4334333
loop_
_publ_author_name
'Yan-Yan Yin'
'Yan-Li Zhao'
'Jian-Gong Ma'
'Xiao-Chang Cao'
'Peng Cheng'
_publ_section_title
;
 Synthesis and Chirality Control of Bulk Crystals and Nanocrystals: From a
 Right-Handed Nonpolar Chain to a Left-Handed Polar Chain
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3738
_journal_page_last               3743
_journal_paper_doi               10.1021/ic302711b
_journal_volume                  52
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C5 H7 Cu N O5 S'
_chemical_formula_weight         256.74
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   5.7404(10)
_cell_length_b                   7.7327(14)
_cell_length_c                   17.870(3)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.48
_cell_volume                     793.2(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1844
_diffrn_reflns_av_sigmaI/netI    0.1639
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5012
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.48
_exptl_absorpt_coefficient_mu    3.003
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_correction_T_min  0.3151
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    2.150
_exptl_crystal_description       prism
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.875
_refine_diff_density_rms         0.142
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1812
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0732
_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)+(0.0258P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1353
_reflns_number_gt                1408
_reflns_number_total             1812
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic302711b_si_001_1.cif
_cod_data_source_block           a
_cod_database_code               4334333
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
O4 O 0.4951(11) 1.0045(6) 0.4877(3) 0.0312(13) Uani 1 1 d .
O5 O 0.6130(12) 0.4698(7) 0.6330(3) 0.0386(14) Uani 1 1 d D
C4 C 0.6131(17) 0.9127(9) 0.5324(4) 0.0292(18) Uani 1 1 d .
Cu1 Cu 0.87852(19) 0.65508(10) 0.59097(5) 0.0263(3) Uani 1 1 d D
S1 S 1.1263(5) 1.1145(2) 0.65627(12) 0.0369(5) Uani 1 1 d .
O3 O 0.6405(12) 0.7530(6) 0.5239(3) 0.0302(13) Uani 1 1 d .
O2 O 1.1584(10) 0.6400(6) 0.6525(3) 0.0314(12) Uani 1 1 d .
N1 N 0.8049(11) 0.8655(7) 0.6531(3) 0.0259(14) Uani 1 1 d .
H1 H 0.6849 0.8417 0.6847 0.031 Uiso 1 1 calc R
O1 O 1.3746(11) 0.7908(6) 0.7331(3) 0.0363(13) Uani 1 1 d .
C2 C 1.1977(15) 0.7719(9) 0.6949(5) 0.030(2) Uani 1 1 d .
C5 C 0.9517(14) 1.0939(9) 0.5729(4) 0.030(2) Uani 1 1 d .
H5D H 0.9152 1.2065 0.5521 0.036 Uiso 1 1 calc R
H5C H 1.0319 1.0258 0.5353 0.036 Uiso 1 1 calc R
C1 C 1.0124(14) 0.9132(9) 0.6964(4) 0.0272(18) Uani 1 1 d .
H1A H 0.9665 0.9344 0.7485 0.033 Uiso 1 1 calc R
C3 C 0.7335(14) 1.0030(9) 0.5992(4) 0.0232(16) Uani 1 1 d .
H3 H 0.6270 1.0852 0.6231 0.028 Uiso 1 1 calc R
H5A H 0.486(6) 0.522(6) 0.642(3) 0.035 Uiso 1 1 d D
H5B H 0.662(8) 0.418(7) 0.671(2) 0.035 Uiso 1 1 d D
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cu Cu 0.3201 1.2651 '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'
S S 0.1246 0.1234 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C4 O4 Cu1 106.2(4) . 3_466
O3 C4 O4 122.9(8) . .
O3 C4 C3 118.9(7) . .
O4 C4 C3 118.2(6) . .
O3 C4 Cu1 76.5(5) . 3_466
O4 C4 Cu1 46.4(4) . 3_466
C3 C4 Cu1 164.5(5) . 3_466
O2 Cu1 O3 159.7(2) . .
O2 Cu1 O4 94.8(2) . 3_566
O3 Cu1 O4 92.4(2) . 3_566
O2 Cu1 N1 84.9(2) . .
O3 Cu1 N1 83.1(2) . .
O4 Cu1 N1 164.2(2) 3_566 .
O2 Cu1 O5 109.6(2) . .
O3 Cu1 O5 88.7(2) . .
O4 Cu1 O5 94.0(2) 3_566 .
N1 Cu1 O5 101.0(2) . .
O2 Cu1 C4 92.2(2) . 3_566
O3 Cu1 C4 85.5(3) . 3_566
O4 Cu1 C4 27.4(2) 3_566 3_566
N1 Cu1 C4 136.8(2) . 3_566
O5 Cu1 C4 120.3(2) . 3_566
O2 Cu1 O3 89.1(2) . 3_566
O3 Cu1 O3 79.55(6) . 3_566
O4 Cu1 O3 54.93(18) 3_566 3_566
N1 Cu1 O3 109.29(19) . 3_566
O5 Cu1 O3 145.71(18) . 3_566
C4 Cu1 O3 27.48(18) 3_566 3_566
C5 S1 C1 92.9(3) . .
C4 O3 Cu1 113.1(6) . .
C4 O3 Cu1 76.0(5) . 3_466
Cu1 O3 Cu1 166.3(3) . 3_466
C2 O2 Cu1 115.3(5) . .
C1 N1 C3 112.6(6) . .
C1 N1 Cu1 108.9(4) . .
C3 N1 Cu1 106.1(4) . .
O1 C2 O2 124.2(7) . .
O1 C2 C1 118.7(7) . .
O2 C2 C1 117.1(8) . .
C3 C5 S1 104.2(5) . .
N1 C1 C2 112.1(6) . .
N1 C1 S1 107.2(5) . .
C2 C1 S1 110.6(6) . .
N1 C3 C5 107.7(6) . .
N1 C3 C4 107.4(6) . .
C5 C3 C4 109.9(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O4 C4 1.265(9) .
O4 Cu1 1.987(5) 3_466
O5 Cu1 2.222(6) .
C4 O3 1.254(8) .
C4 C3 1.546(10) .
C4 Cu1 2.636(8) 3_466
Cu1 O2 1.950(5) .
Cu1 O3 1.969(6) .
Cu1 O4 1.987(5) 3_566
Cu1 N1 2.015(6) .
Cu1 C4 2.636(8) 3_566
Cu1 O3 2.642(5) 3_566
S1 C5 1.803(8) .
S1 C1 1.835(7) .
O3 Cu1 2.642(5) 3_466
O2 C2 1.291(8) .
N1 C1 1.468(9) .
N1 C3 1.492(9) .
O1 C2 1.232(9) .
C2 C1 1.525(10) .
C5 C3 1.511(11) .
