#------------------------------------------------------------------------------
#$Date: 2015-06-16 10:53:26 +0300 (Tue, 16 Jun 2015) $
#$Revision: 139259 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/73/7117309.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_7117309
loop_
_publ_author_name
'Zongjun Qiao'
'Nanyang Ge'
'Xuefeng Jiang'
_publ_section_title
;
 CO2-promoted oxidative cross-coupling reaction for C-S bond formation via
 masked strategy in an odourless way
;
_journal_name_full               Chem.Commun.
_journal_page_first              10295
_journal_paper_doi               10.1039/C5cc03038B
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C8 H24 Cu N4, 2(C7 H6 F O3 S2), 2(H2 O)'
_chemical_formula_sum            'C22 H40 Cu F2 N4 O8 S4'
_chemical_formula_weight         718.36
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-04-24 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                92.852(3)
_cell_angle_beta                 93.152(4)
_cell_angle_gamma                107.116(3)
_cell_formula_units_Z            1
_cell_length_a                   7.5312(15)
_cell_length_b                   8.2038(16)
_cell_length_c                   13.344(3)
_cell_measurement_reflns_used    3444
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.37
_cell_measurement_theta_min      2.60
_cell_volume                     784.9(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5492
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         1.532
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.023
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0659 before and 0.0349 after correction.
The Ratio of minimum to maximum transmission is 0.6881.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             375
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.860
_refine_diff_density_min         -0.930
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0619
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0926P)²+2.4990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1716
_refine_ls_wR_factor_ref         0.1777
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                2753
_reflns_number_total             3094
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc03038b2.cif
_cod_data_source_block           mo_dm14546_0m
_cod_database_code               7117309
_shelxl_version_number           2014-3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.862
_shelx_estimated_absorpt_t_min   0.685
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O4(H4D,H4E)
2.b Ternary CH refined with riding coordinates:
 N1(H1), N2(H2)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C), C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -0.5000 0.0000 -0.5000 0.0165(2) Uani 1 2 d S T P . .
N1 N -0.2674(5) 0.1566(4) -0.4181(3) 0.0190(7) Uani 1 1 d . . . . .
H1 H -0.3085 0.2465 -0.3810 0.023 Uiso 1 1 calc R . . . .
N2 N -0.3989(5) 0.1370(4) -0.6184(3) 0.0198(7) Uani 1 1 d . . . . .
H2 H -0.5027 0.1740 -0.6503 0.024 Uiso 1 1 calc R . . . .
C1 C -0.1681(6) 0.0828(6) -0.3423(3) 0.0247(9) Uani 1 1 d . . . . .
H1A H -0.2479 0.0450 -0.2872 0.037 Uiso 1 1 calc GR . . . .
H1B H -0.0531 0.1696 -0.3158 0.037 Uiso 1 1 calc GR . . . .
H1C H -0.1375 -0.0151 -0.3738 0.037 Uiso 1 1 calc GR . . . .
C2 C -0.1393(6) 0.2450(6) -0.4916(3) 0.0237(9) Uani 1 1 d . . . . .
H2A H -0.0712 0.1685 -0.5193 0.028 Uiso 1 1 calc R . . . .
H2B H -0.0471 0.3484 -0.4584 0.028 Uiso 1 1 calc R . . . .
C3 C -0.2528(6) 0.2944(6) -0.5754(4) 0.0235(9) Uani 1 1 d . . . . .
H3A H -0.3117 0.3791 -0.5487 0.028 Uiso 1 1 calc R . . . .
H3B H -0.1713 0.3463 -0.6282 0.028 Uiso 1 1 calc R . . . .
C4 C -0.3273(7) 0.0480(6) -0.6981(4) 0.0264(10) Uani 1 1 d . . . . .
H4A H -0.2156 0.0222 -0.6712 0.040 Uiso 1 1 calc GR . . . .
H4B H -0.2958 0.1214 -0.7542 0.040 Uiso 1 1 calc GR . . . .
H4C H -0.4228 -0.0587 -0.7218 0.040 Uiso 1 1 calc GR . . . .
S1 S -0.08396(15) -0.43967(18) -0.20027(9) 0.0304(3) Uani 1 1 d . . . . .
S2 S -0.31172(14) -0.43622(14) -0.29549(8) 0.0204(3) Uani 1 1 d . . . . .
F1 F -0.1823(8) -0.1088(8) 0.1067(4) 0.0978(18) Uani 1 1 d . . . . .
O1 O -0.2240(5) -0.4028(5) -0.3898(2) 0.0342(8) Uani 1 1 d . . . . .
O2 O -0.4447(5) -0.6059(4) -0.2989(3) 0.0309(8) Uani 1 1 d . . . . .
O3 O -0.3850(5) -0.3041(4) -0.2570(2) 0.0291(7) Uani 1 1 d . . . . .
C5 C -0.1799(7) -0.4505(9) -0.0822(4) 0.0410(14) Uani 1 1 d . . . . .
C6 C -0.1534(9) -0.2729(12) -0.0321(5) 0.062(2) Uani 1 1 d . . . . .
H6 H -0.0997 -0.1720 -0.0652 0.074 Uiso 1 1 calc R . . . .
C7 C -0.2087(10) -0.2670(11) 0.0588(6) 0.063(2) Uani 1 1 d . . . . .
C8 C -0.2935(9) -0.4121(12) 0.1077(6) 0.065(2) Uani 1 1 d . . . . .
H8 H -0.3318 -0.3992 0.1735 0.078 Uiso 1 1 calc R . . . .
C9 C -0.3230(8) -0.5702(13) 0.0646(5) 0.061(2) Uani 1 1 d . . . . .
H9 H -0.3833 -0.6681 0.0986 0.073 Uiso 1 1 calc R . . . .
C10 C -0.2610(8) -0.5875(10) -0.0345(5) 0.0532(17) Uani 1 1 d . . . . .
C11 C -0.2889(11) -0.7521(12) -0.0818(6) 0.070(2) Uani 1 1 d . . . . .
H11A H -0.1699 -0.7625 -0.1029 0.105 Uiso 1 1 calc GR . . . .
H11B H -0.3773 -0.7689 -0.1408 0.105 Uiso 1 1 calc GR . . . .
H11C H -0.3389 -0.8388 -0.0345 0.105 Uiso 1 1 calc GR . . . .
O4 O -0.6740(4) 0.2090(4) -0.4642(3) 0.0254(7) Uani 1 1 d . . . . .
H4D H -0.7582 0.1137 -0.4636 0.038 Uiso 1 1 d G . . . .
H4E H -0.7029 0.2660 -0.5105 0.038 Uiso 1 1 d G . . . .
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'
F F 0.0171 0.0103 '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
N1 Cu1 N1 180.0 . 2_454
N2 Cu1 N1 94.52(14) . 2_454
N2 Cu1 N1 85.48(14) 2_454 2_454
N2 Cu1 N1 85.48(14) . .
N2 Cu1 N1 94.52(14) 2_454 .
N2 Cu1 N2 180.0 . 2_454
Cu1 N1 H1 106.5 . .
C1 N1 Cu1 119.3(3) . .
C1 N1 H1 106.5 . .
C2 N1 Cu1 106.6(3) . .
C2 N1 H1 106.5 . .
C2 N1 C1 110.8(3) . .
Cu1 N2 H2 107.3 . .
C3 N2 Cu1 106.6(3) . .
C3 N2 H2 107.3 . .
C4 N2 Cu1 116.7(3) . .
C4 N2 H2 107.3 . .
C4 N2 C3 111.1(3) . .
N1 C1 H1A 109.5 . .
N1 C1 H1B 109.5 . .
N1 C1 H1C 109.5 . .
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N1 C2 H2A 110.0 . .
N1 C2 H2B 110.0 . .
N1 C2 C3 108.4(3) . .
H2A C2 H2B 108.4 . .
C3 C2 H2A 110.0 . .
C3 C2 H2B 110.0 . .
N2 C3 C2 108.4(3) . .
N2 C3 H3A 110.0 . .
N2 C3 H3B 110.0 . .
C2 C3 H3A 110.0 . .
C2 C3 H3B 110.0 . .
H3A C3 H3B 108.4 . .
N2 C4 H4A 109.5 . .
N2 C4 H4B 109.5 . .
N2 C4 H4C 109.5 . .
H4A C4 H4B 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C5 S1 S2 101.18(16) . .
O1 S2 S1 100.50(15) . .
O2 S2 S1 106.90(15) . .
O2 S2 O1 111.9(2) . .
O3 S2 S1 108.55(15) . .
O3 S2 O1 114.7(2) . .
O3 S2 O2 113.1(2) . .
C6 C5 S1 111.6(4) . .
C10 C5 S1 128.7(6) . .
C10 C5 C6 119.6(6) . .
C5 C6 H6 121.8 . .
C7 C6 C5 116.4(7) . .
C7 C6 H6 121.8 . .
F1 C7 C8 119.2(7) . .
C6 C7 F1 117.7(8) . .
C6 C7 C8 123.1(8) . .
C7 C8 H8 119.1 . .
C9 C8 C7 121.9(8) . .
C9 C8 H8 119.1 . .
C8 C9 H9 120.8 . .
C8 C9 C10 118.4(8) . .
C10 C9 H9 120.8 . .
C5 C10 C9 120.5(8) . .
C5 C10 C11 119.6(7) . .
C11 C10 C9 119.9(7) . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
H4D O4 H4E 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 2.059(3) .
Cu1 N1 2.059(3) 2_454
Cu1 N2 2.036(4) .
Cu1 N2 2.036(4) 2_454
N1 H1 1.0000 .
N1 C1 1.481(5) .
N1 C2 1.477(5) .
N2 H2 1.0000 .
N2 C3 1.493(5) .
N2 C4 1.474(6) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C2 C3 1.512(6) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
S1 S2 2.0857(15) .
S1 C5 1.764(5) .
S2 O1 1.454(3) .
S2 O2 1.453(3) .
S2 O3 1.439(3) .
F1 C7 1.372(9) .
C5 C6 1.526(11) .
C5 C10 1.324(9) .
C6 H6 0.9500 .
C6 C7 1.307(10) .
C7 C8 1.388(11) .
C8 H8 0.9500 .
C8 C9 1.343(12) .
C9 H9 0.9500 .
C9 C10 1.440(9) .
C10 C11 1.414(11) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
O4 H4D 0.8500 .
O4 H4E 0.8499 .
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
O4 H4E O1 0.85 1.94 2.789(5) 176.5 2_454
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
Cu1 N1 C2 C3 40.4(4) . . . .
Cu1 N2 C3 C2 41.2(4) . . . .
N1 C2 C3 N2 -55.5(4) . . . .
C1 N1 C2 C3 171.7(3) . . . .
C4 N2 C3 C2 -87.0(4) . . . .
S1 C5 C6 C7 -175.6(5) . . . .
S1 C5 C10 C9 176.9(4) . . . .
S1 C5 C10 C11 -4.0(8) . . . .
S2 S1 C5 C6 -90.4(4) . . . .
S2 S1 C5 C10 92.1(5) . . . .
F1 C7 C8 C9 -180.0(6) . . . .
C5 C6 C7 F1 178.4(6) . . . .
C5 C6 C7 C8 -2.3(10) . . . .
C6 C5 C10 C9 -0.5(8) . . . .
C6 C5 C10 C11 178.7(5) . . . .
C6 C7 C8 C9 0.7(11) . . . .
C7 C8 C9 C10 1.1(9) . . . .
C8 C9 C10 C5 -1.2(8) . . . .
C8 C9 C10 C11 179.7(6) . . . .
C10 C5 C6 C7 2.2(8) . . . .
