# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_2112
_database_code_depnum_ccdc_archive 'CCDC 1873665'
loop_
_audit_author_name
_audit_author_address
'Xiaopeng Xuan'
;Henan normal university
China
;
_audit_update_record             
;
2019-10-10 deposited with the CCDC.	2019-10-10 downloaded from the CCDC.
;
_audit_creation_date             2019-10-10
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C20 H4 Cu4 O18), H6 O2'
_chemical_formula_sum            'C10 H8 Cu2 O11'
_chemical_formula_weight         431.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           10
_space_group_name_H-M_alt        'P 1 2/m 1'
_space_group_name_Hall           '-P 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'-x, -y, -z'
'x, -y, z'

_cell_length_a                   7.8682(3)
_cell_length_b                   10.5629(4)
_cell_length_c                   11.6070(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.552(5)
_cell_angle_gamma                90
_cell_volume                     924.70(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1707
_cell_measurement_temperature    298.3(1)
_cell_measurement_theta_max      70.3340
_cell_measurement_theta_min      4.2100
_shelx_estimated_absorpt_T_max   0.589
_shelx_estimated_absorpt_T_min   0.560
_exptl_absorpt_coefficient_mu    3.285
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4226
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.337
_diffrn_reflns_theta_min         4.185
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.3(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00 -19.00   0.50    0.05    --   -2.46  57.00 150.00   62
  2  ω      3.00  29.00   0.50    0.05    --   -2.46  57.00 150.00   52
  3  ω     54.00  80.00   0.50    0.05    --   -2.46  57.00 150.00   52
  4  ω      0.00  41.00   0.50    0.05    --   -2.46 -99.00 -30.00   82
  5  ω     40.00  65.00   0.50    0.05    --    2.46-138.00  83.00   50
  6  ω     97.00 122.00   0.50    0.06    --   59.04-131.00-101.00   50
  7  ω     39.00 119.00   0.50    0.06    --  115.63-131.00-101.00  160
  8  ω     64.00 123.00   0.50    0.06    --  115.63-138.00  83.00  118
  9  ω    139.00 177.00   0.50    0.06    --  115.63  63.00 120.00   76
 10  ω    101.00 144.00   0.50    0.06    --  115.63 111.00 -60.00   86
 11  ω    110.00 137.00   0.50    0.06    --  115.63 178.00-180.00   54
 12  ω     60.00 104.00   0.50    0.06    --  115.63 178.00-180.00   88
 13  ω     60.00 125.00   0.50    0.06    --  115.63 178.00 -90.00  130
 14  ω     60.00 148.00   0.50    0.06    --  115.63 178.00  30.00  176
 15  ω     72.00 119.00   0.50    0.06    --  115.63  63.00 120.00   94
 16  ω     61.00 113.00   0.50    0.06    --  115.63 178.00  90.00  104
 17  ω    -70.00 -44.00   0.50    0.05    --   -2.46 178.00  30.00   52
 18  ω    -73.00 -48.00   0.50    0.05    --   -2.46 131.00 -29.00   50
 19  ω    -75.00 -50.00   0.50    0.05    --    2.46 138.00 145.00   50
 20  ω   -101.00 -17.00   0.50    0.06    --  -59.04 138.00 145.00  168
 21  ω    -52.00 -27.00   0.50    0.06    -- -106.00 138.00 145.00   50
 22  ω    -87.00 -54.00   0.50    0.06    -- -106.00 111.00 120.00   66
 23  ω   -159.00-104.00   0.50    0.06    -- -106.00 -91.00   0.00  110
 24  ω    -93.00 -68.00   0.50    0.06    --  -59.04-138.00  83.00   50
 25  ω   -137.00 -80.00   0.50    0.06    --  -59.04 -94.00  90.00  114
 26  ω   -162.00 -83.00   0.50    0.06    --  -59.04 -94.00 150.00  158
 27  ω   -162.00-116.00   0.50    0.06    --  -59.04 -94.00 -60.00   92
 28  ω   -110.00 -84.00   0.50    0.06    --  -59.04 -94.00 -60.00   52
 29  ω   -110.00 -84.00   0.50    0.06    --  -59.04 -94.00 -90.00   52
 30  ω   -127.00 -67.00   0.50    0.06    --  -59.04-131.00-101.00  120
 31  ω   -122.00 -89.00   0.50    0.06    --  -59.04 -94.00-180.00   66
 32  ω   -134.00 -72.00   0.50    0.06    -- -106.00-131.00-101.00  124
 33  ω   -106.00 -78.00   0.50    0.06    -- -106.00-111.00-150.00   56
 34  ω   -158.00-133.00   0.50    0.06    --  -59.04 -94.00 -90.00   50
 35  ω   -171.00-144.00   0.50    0.06    -- -106.00-111.00-150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0726480000
_diffrn_orient_matrix_UB_12      0.0597549000
_diffrn_orient_matrix_UB_13      0.0975340000
_diffrn_orient_matrix_UB_21      -0.0390683000
_diffrn_orient_matrix_UB_22      -0.1329480000
_diffrn_orient_matrix_UB_23      0.0407202000
_diffrn_orient_matrix_UB_31      0.1867770000
_diffrn_orient_matrix_UB_32      -0.0046288000
_diffrn_orient_matrix_UB_33      0.0895254000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1729
_reflns_number_total             1848
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.098
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.167
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         1848
_refine_ls_number_restraints     171
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      1.111
_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)+(0.1164P)²+1.4680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1740
_refine_ls_wR_factor_ref         0.1771
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C3-C5A
 1.48 with sigma of 0.01
3. Restrained planarity
 C5A, O3A, O4A, C3
 with sigma of 0.01
 C3, C5, O3, O4
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
O2 \\sim O2A \\sim C1: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
C5 \\sim O4 \\sim O3 \\sim C5A \\sim O4A \\sim O3A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(O2A) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C5) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(C5A) \\sim
Ueq, Uanis(O4A) \\sim Ueq, Uanis(O3A) \\sim Ueq: with sigma of 0.01 and sigma
for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 O2, O2A, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C5, O4, O3, C5A, O4A, O3A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
6. Others
 Sof(C5A)=Sof(O4A)=Sof(O3A)=0.5*(1-FVAR(2))
 Sof(C5)=Sof(O4)=Sof(O3)=0.5*FVAR(2)
 Sof(O2A)=0.5*(1-FVAR(3))
 Sof(O2)=0.5*FVAR(3)
 Fixed Sof: O10(0.25) O11(0.25) O8(0.25) O9(0.25)
7.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.36710(9) 0.500000 0.64336(6) 0.0188(3) Uani 1 2 d S T P . .
Cu2 Cu 0.000000 0.36288(7) 0.500000 0.0216(3) Uani 1 2 d S T P . .
O7 O 0.1665(4) 0.500000 0.5045(3) 0.0128(7) Uani 1 2 d S T P . .
O6 O -0.4243(4) 0.3159(3) 0.3928(3) 0.0299(7) Uani 1 1 d . . . . .
O1 O 0.5531(5) 0.500000 0.7921(3) 0.0311(10) Uani 1 2 d S T P A .
O5 O -0.1671(3) 0.2338(3) 0.5053(3) 0.0331(7) Uani 1 1 d . . . . .
C6 C -0.3329(5) 0.2344(3) 0.4583(4) 0.0214(8) Uani 1 1 d . . . . .
C7 C -0.4215(5) 0.1147(4) 0.4822(4) 0.0219(8) Uani 1 1 d . . . . .
C8 C -0.3451(7) 0.000000 0.4664(6) 0.0242(11) Uani 1 2 d S T P . .
H8 H -0.240047 0.000000 0.444687 0.029 Uiso 1 2 calc RS T P . .
C2 C 0.8608(7) 0.500000 0.8932(5) 0.0247(12) Uani 1 2 d S T P A .
O2 O 0.730(2) 0.500000 0.6832(11) 0.027(5) Uani 0.47(5) 2 d S TU P A 2
C1 C 0.7075(7) 0.500000 0.7816(5) 0.0260(12) Uani 1 2 d S TU P . .
C3 C 1.0359(7) 0.500000 0.8884(5) 0.0288(13) Uani 1 2 d DS T P . .
C4 C 1.1726(7) 0.500000 0.9948(5) 0.0308(14) Uani 1 2 d S T P A .
H4 H 1.289277 0.500000 0.991556 0.037 Uiso 1 2 calc RS T P . .
C5 C 1.095(2) 0.525(3) 0.769(2) 0.017(3) Uani 0.27(4) 1 d . U . A -2
O4 O 1.077(4) 0.624(3) 0.725(2) 0.022(4) Uani 0.27(4) 1 d . U . A -2
O3 O 1.158(4) 0.424(3) 0.738(2) 0.024(4) Uani 0.27(4) 1 d . U . A -2
O10 O 0.222(3) 0.224(3) 0.840(2) 0.087(6) Uiso 0.25 1 d . . . . .
O11 O 0.010(4) 0.075(4) 0.709(3) 0.133(11) Uiso 0.25 1 d . . . B 2
O8 O 0.749(4) 0.192(4) 0.790(3) 0.125(10) Uiso 0.25 1 d . . . . .
O9 O 0.970(4) 0.155(3) 0.786(3) 0.113(9) Uiso 0.25 1 d . . . C 1
C5A C 1.091(3) 0.465(4) 0.7806(11) 0.018(4) Uani 0.23(4) 1 d D U . A -1
O4A O 1.194(4) 0.543(3) 0.753(2) 0.019(4) Uani 0.23(4) 1 d . U . A -1
O3A O 1.038(5) 0.358(3) 0.714(3) 0.026(5) Uani 0.23(4) 1 d . U . A -1
O2A O 0.749(2) 0.445(3) 0.6879(12) 0.027(3) Uani 0.26(3) 1 d . U . A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O7 1.908(3) . ?
Cu1 O6 2.066(3) 3_566 ?
Cu1 O6 2.066(3) 2_556 ?
Cu1 O1 1.919(4) . ?
Cu2 Cu2 2.8968(15) 3_566 ?
Cu2 O7 1.944(2) . ?
Cu2 O7 1.944(2) 3_566 ?
Cu2 O5 1.907(3) . ?
Cu2 O5 1.907(3) 2_556 ?
O6 C6 1.234(5) . ?
O1 C1 1.255(7) . ?
O5 C6 1.263(5) . ?
C6 C7 1.508(5) . ?
C7 C7 1.410(7) 2_456 ?
C7 C8 1.387(4) . ?
C2 C1 1.498(7) . ?
C2 C3 1.395(7) . ?
C2 C4 1.397(7) 3_767 ?
O2 C1 1.205(14) . ?
C1 O2A 1.350(18) . ?
C1 O2A 1.350(18) 4_565 ?
C3 C4 1.387(8) . ?
C3 C5 1.61(2) . ?
C3 C5A 1.483(10) . ?
C5 O4 1.16(4) . ?
C5 O3 1.27(4) . ?
O11 O11 1.59(7) 4 ?
C5A O4A 1.26(4) . ?
C5A O3A 1.36(5) . ?
O2A O2A 1.16(6) 4_565 ?

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
_geom_angle_publ_flag
O7 Cu1 O6 90.22(9) . 3_566 ?
O7 Cu1 O6 90.22(9) . 2_556 ?
O7 Cu1 O1 174.50(15) . . ?
O6 Cu1 O6 140.57(18) 2_556 3_566 ?
O1 Cu1 O6 91.63(9) . 2_556 ?
O1 Cu1 O6 91.63(9) . 3_566 ?
O7 Cu2 Cu2 41.82(7) . 3_566 ?
O7 Cu2 Cu2 41.82(7) 3_566 3_566 ?
O7 Cu2 O7 83.64(14) 3_566 . ?
O5 Cu2 Cu2 135.64(9) 2_556 3_566 ?
O5 Cu2 Cu2 135.64(9) . 3_566 ?
O5 Cu2 O7 93.91(11) . 3_566 ?
O5 Cu2 O7 175.90(13) . . ?
O5 Cu2 O7 175.90(14) 2_556 3_566 ?
O5 Cu2 O7 93.91(11) 2_556 . ?
O5 Cu2 O5 88.72(18) . 2_556 ?
Cu1 O7 Cu2 114.30(11) . . ?
Cu1 O7 Cu2 114.30(11) . 3_566 ?
Cu2 O7 Cu2 96.36(14) . 3_566 ?
C6 O6 Cu1 131.2(2) . 3_566 ?
C1 O1 Cu1 115.1(3) . . ?
C6 O5 Cu2 128.3(3) . . ?
O6 C6 O5 128.2(3) . . ?
O6 C6 C7 118.7(3) . . ?
O5 C6 C7 113.0(3) . . ?
C7 C7 C6 122.92(19) 2_456 . ?
C8 C7 C6 117.9(3) . . ?
C8 C7 C7 119.2(2) . 2_456 ?
C7 C8 C7 121.6(5) 4 . ?
C3 C2 C1 121.8(5) . . ?
C3 C2 C4 119.1(5) . 3_767 ?
C4 C2 C1 119.1(5) 3_767 . ?
O1 C1 C2 118.7(4) . . ?
O1 C1 O2A 122.6(8) . 4_565 ?
O1 C1 O2A 122.6(8) . . ?
O2 C1 O1 120.0(9) . . ?
O2 C1 C2 121.3(8) . . ?
O2 C1 O2A 26.1(11) . 4_565 ?
O2A C1 C2 112.2(9) 4_565 . ?
O2A C1 C2 112.2(9) . . ?
O2A C1 O2A 51(2) 4_565 . ?
C2 C3 C5 124.5(8) . . ?
C2 C3 C5A 124.2(12) . . ?
C4 C3 C2 119.2(5) . . ?
C4 C3 C5 115.4(6) . . ?
C4 C3 C5A 114.4(9) . . ?
C3 C4 C2 121.7(5) . 3_767 ?
O4 C5 C3 120(2) . . ?
O4 C5 O3 130(3) . . ?
O3 C5 C3 110(2) . . ?
O4A C5A C3 114(3) . . ?
O4A C5A O3A 120.7(19) . . ?
O3A C5A C3 125(3) . . ?
O2A O2A C1 64.7(11) 4_565 . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.521
_oxdiff_exptl_absorpt_empirical_full_min 0.774
