data_exp_118
_audit_creation_date              2019-04-18
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C10 H14 Cu O4'
_chemical_formula_sum             'C10 H14 Cu O4'
_chemical_formula_weight          261.75
_chemical_melting_point           ?
_chemical_oxdiff_formula          'C10 H14 Cu O4'
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'
 'O' 'O' 0.0106 0.0060 '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            14
_space_group_name_H-M_alt         'P 1 21/n 1'
_space_group_name_Hall            '-P 2yn'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                    10.2283(12)
_cell_length_b                    4.6767(6)
_cell_length_c                    11.2851(19)
_cell_angle_alpha                 90
_cell_angle_beta                  91.994(13)
_cell_angle_gamma                 90
_cell_volume                      539.49(13)
_cell_formula_units_Z             2
_cell_measurement_reflns_used     1304
_cell_measurement_temperature     293(2)
_cell_measurement_theta_max       28.0130
_cell_measurement_theta_min       2.6360
_shelx_estimated_absorpt_T_max    ?
_shelx_estimated_absorpt_T_min    ?
_exptl_absorpt_coefficient_mu     2.014
_exptl_absorpt_correction_T_max   0.821
_exptl_absorpt_correction_T_min   0.520
_exptl_absorpt_correction_type    analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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     1.611
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_description        needle
_exptl_crystal_F_000              270
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 14 0 -5 0.0666
 1 -7 2 0.3338
 10 4 -8 0.1538
 -5 0 -15 0.0611
 5 0 15 0.0675
 -4 -1 -5 0.1469
 5 1 5 0.0902
 14 0 0 0.0750
 -14 0 0 0.0570
 -1 3 -5 0.2184

_exptl_crystal_size_max           0.651
_exptl_crystal_size_mid           0.161
_exptl_crystal_size_min           0.13
loop_
  _exptl_oxdiff_crystal_face_indexfrac_h
  _exptl_oxdiff_crystal_face_indexfrac_k
  _exptl_oxdiff_crystal_face_indexfrac_l
  _exptl_oxdiff_crystal_face_x
  _exptl_oxdiff_crystal_face_y
  _exptl_oxdiff_crystal_face_z
 13.8263 -0.1383 -5.0300 0.3859 -0.4286 0.8170
 1.0234 -6.5067 2.2241 0.5645 -0.6270 -0.5369
 9.6520 3.5825 -8.4040 0.1223 0.1684 0.9781
 -4.5382 0.4882 -14.8800 0.5846 0.8046 0.1047
 4.6533 -0.4523 14.8396 -0.5851 -0.8054 -0.0948
 -4.0000 -1.0000 -5.0000 0.2883 0.2906 -0.1924
 5.0000 1.0000 5.0000 -0.2780 -0.3347 0.2450
 14.4143 0.1363 0.0253 0.1331 -0.6262 0.7682
 -14.4096 -0.0033 -0.2342 -0.1369 0.6441 -0.7526
 -1.0000 3.0000 -5.0000 -0.0840 0.4639 0.3005

_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0403
_diffrn_reflns_av_unetI/netI      0.0437
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_k_min        -6
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_number             4171
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full         26.000
_diffrn_reflns_theta_max          27.485
_diffrn_reflns_theta_min          2.642
_diffrn_ambient_temperature       293(2)
_diffrn_detector                  'CCD plate'
_diffrn_detector_area_resol_mean  10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -74.00 110.00   0.50    4.83    --   20.00  54.00 -30.00  368
  2  ω    -74.00   4.00   0.50    4.83    --   20.00  54.00  90.00  156
  3  ω    -74.00 -32.00   0.50    4.83    --   20.00  54.00-120.00   84
  4  ω     -7.00  39.00   0.50    4.83    --   20.00  54.00-120.00   92
  5  ω     80.00 107.00   0.50    4.83    --   20.00  54.00-120.00   54
  6  ω    -74.00 104.00   0.50    4.83    --   20.00  54.00   0.00  356
;
_diffrn_measurement_device        'two-circle diffractometer'
_diffrn_measurement_device_type   'XtaLAB Mini II'
_diffrn_measurement_method        'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11       0.0102672000
_diffrn_orient_matrix_UB_12       -0.1007745000
_diffrn_orient_matrix_UB_13       -0.0457222000
_diffrn_orient_matrix_UB_21       -0.0440981000
_diffrn_orient_matrix_UB_22       0.0763925000
_diffrn_orient_matrix_UB_23       -0.0381152000
_diffrn_orient_matrix_UB_31       0.0525384000
_diffrn_orient_matrix_UB_32       0.0838331000
_diffrn_orient_matrix_UB_33       -0.0203082000
_diffrn_radiation_monochromator   graphite
_diffrn_radiation_probe           x-ray
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    'fine-focus sealed X-ray tube'
_diffrn_source_type               'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_full     .
_reflns_Friedel_fraction_max      .
_reflns_number_gt                 974
_reflns_number_total              1229
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric  1
_reflns_odcompleteness_theta      26.32
_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 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction         'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_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          0.786
_refine_diff_density_min          -1.210
_refine_diff_density_rms          0.131
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.065
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      72
_refine_ls_number_reflns          1229
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0631
_refine_ls_R_factor_gt            0.0516
_refine_ls_restrained_S_all       1.065
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0992P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1390
_refine_ls_wR_factor_ref          0.1477
_refine_special_details           ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C)
;
_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 0.5000 0.0000 0.5000 0.0373(3) Uani 1 2 d S T P . .
 O1 O 0.3386(2) 0.2024(4) 0.49421(18) 0.0421(5) Uani 1 1 d . . . . .
 O2 O 0.5654(2) 0.1961(5) 0.36587(18) 0.0426(6) Uani 1 1 d . . . . .
 C2 C 0.3114(3) 0.4119(8) 0.4267(3) 0.0371(7) Uani 1 1 d . . . . .
 C4 C 0.5115(3) 0.4075(8) 0.3143(3) 0.0371(7) Uani 1 1 d . . . . .
 C3 C 0.3911(4) 0.5189(6) 0.3415(3) 0.0412(8) Uani 1 1 d . . . . .
 H3 H 0.3617 0.6782 0.2990 0.049 Uiso 1 1 calc R . . . .
 C1 C 0.1841(4) 0.5536(8) 0.4478(4) 0.0485(9) Uani 1 1 d . . . . .
 H1A H 0.1224 0.4139 0.4734 0.073 Uiso 1 1 calc GR . . . .
 H1B H 0.1515 0.6412 0.3757 0.073 Uiso 1 1 calc GR . . . .
 H1C H 0.1962 0.6973 0.5080 0.073 Uiso 1 1 calc GR . . . .
 C5 C 0.5874(4) 0.5392(8) 0.2178(3) 0.0518(10) Uani 1 1 d . . . . .
 H5A H 0.6312 0.7076 0.2473 0.078 Uiso 1 1 calc GR . . . .
 H5B H 0.5288 0.5901 0.1528 0.078 Uiso 1 1 calc GR . . . .
 H5C H 0.6509 0.4048 0.1911 0.078 Uiso 1 1 calc GR . . . .


_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 O1 1.902(2) 3_656 ?
 Cu1 O1 1.902(2) . ?
 Cu1 O2 1.911(2) . ?
 Cu1 O2 1.911(2) 3_656 ?
 O1 C2 1.266(4) . ?
 O2 C4 1.264(4) . ?
 C2 C3 1.376(5) . ?
 C2 C1 1.488(5) . ?
 C4 C3 1.382(5) . ?
 C4 C5 1.492(4) . ?
 C3 H3 0.9300 . ?
 C1 H1A 0.9600 . ?
 C1 H1B 0.9600 . ?
 C1 H1C 0.9600 . ?
 C5 H5A 0.9600 . ?
 C5 H5B 0.9600 . ?
 C5 H5C 0.9600 . ?

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
 O1 Cu1 O1 180.0 3_656 . ?
 O1 Cu1 O2 93.52(9) 3_656 3_656 ?
 O1 Cu1 O2 86.48(9) . 3_656 ?
 O1 Cu1 O2 86.48(9) 3_656 . ?
 O1 Cu1 O2 93.52(9) . . ?
 O2 Cu1 O2 180.0 . 3_656 ?
 C2 O1 Cu1 125.3(2) . . ?
 C4 O2 Cu1 125.5(2) . . ?
 O1 C2 C3 125.4(3) . . ?
 O1 C2 C1 115.1(3) . . ?
 C3 C2 C1 119.5(3) . . ?
 O2 C4 C3 124.8(3) . . ?
 O2 C4 C5 115.5(3) . . ?
 C3 C4 C5 119.8(3) . . ?
 C2 C3 C4 124.9(3) . . ?
 C2 C3 H3 117.5 . . ?
 C4 C3 H3 117.5 . . ?
 C2 C1 H1A 109.5 . . ?
 C2 C1 H1B 109.5 . . ?
 C2 C1 H1C 109.5 . . ?
 H1A C1 H1B 109.5 . . ?
 H1A C1 H1C 109.5 . . ?
 H1B C1 H1C 109.5 . . ?
 C4 C5 H5A 109.5 . . ?
 C4 C5 H5B 109.5 . . ?
 C4 C5 H5C 109.5 . . ?
 H5A C5 H5B 109.5 . . ?
 H5A C5 H5C 109.5 . . ?
 H5B C5 H5C 109.5 . . ?

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
  _geom_torsion_publ_flag
 Cu1 O1 C2 C3 3.8(5) . . . . ?
 Cu1 O1 C2 C1 -173.7(2) . . . . ?
 Cu1 O2 C4 C3 -4.9(5) . . . . ?
 Cu1 O2 C4 C5 175.0(2) . . . . ?
 O1 C2 C3 C4 2.2(6) . . . . ?
 O2 C4 C3 C2 -1.6(6) . . . . ?
 C1 C2 C3 C4 179.6(4) . . . . ?
 C5 C4 C3 C2 178.6(4) . . . . ?

_shelx_SHELXL_version_number      '2014/7'
_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 1.691
_oxdiff_exptl_absorpt_empirical_full_min 0.637

