#------------------------------------------------------------------------------
#$Date: 2022-02-21 11:53:56 +0200 (Mon, 21 Feb 2022) $
#$Revision: 273054 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/45/8104570.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_8104570
loop_
_publ_author_name
'Yang, Fei'
'Liu, Pengju'
'Guo, Libing'
'Xian, Dong'
_publ_section_title
;
 The crystal structure of bis(benzoato-κ2
 O,O′)-(2,9-dimethyl-1,10-phenanthroline-κ2
 N,N′)-copper(II), C28H22CuN2O4
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1219
_journal_page_last               1221
_journal_paper_doi               10.1515/ncrs-2021-0283
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C14 H11 Cu0.5 N O2'
_chemical_formula_sum            'C14 H11 Cu0.5 N O2'
_chemical_formula_weight         257.01
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90.580(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.2971(3)
_cell_length_b                   14.4409(3)
_cell_length_c                   9.5617(2)
_cell_measurement_reflns_used    3371
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.3380
_cell_measurement_theta_min      6.0750
_cell_volume                     2388.25(8)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009) [1]'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009) [1]'
_computing_molecular_graphics    'Diamond 3.2i [2]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009) [3]'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2018) [4]'
_computing_structure_solution    'SHELXS  (Sheldrick, 2018) [5]'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -76.00  18.00   1.00    1.00    --  -35.62 101.00  55.00   94
  2  ω      4.00  76.00   1.00    1.00    --   35.62-101.00 -48.00   72
  3  ω     37.00 110.00   1.00    3.26    --  107.12-101.00 -48.00   73
  4  ω    101.00 177.00   1.00    3.26    --  107.12 101.00  55.00   76
  5  ω   -105.00 -17.00   1.00    1.00    --  -35.62 -38.00-150.00   88
  6  ω   -107.00 -36.00   1.00    1.00    --  -35.62-178.00 120.00   71
  7  ω     59.00 107.00   1.00    1.00    --   35.62-178.00-120.00   48
  8  ω     59.00  85.00   1.00    3.26    --  107.12 -95.00-120.00   26
  9  ω     97.00 173.00   1.00    3.26    --  107.12  61.00  90.00   76
 10  ω    149.00 176.00   1.00    3.26    --  107.12 111.00 -30.00   27
 11  ω    102.00 131.00   1.00    3.26    --  107.12 111.00 -30.00   29
 12  ω     42.00  82.00   1.00    3.26    --  107.12 -95.00  60.00   40
 13  ω     43.00 101.00   1.00    3.26    --  107.12 -61.00 -60.00   58
 14  ω     81.00 175.00   1.00    3.26    --  107.12  77.00-150.00   94
 15  ω     43.00 123.00   1.00    3.26    --  107.12 -61.00  90.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0253489000
_diffrn_orient_matrix_UB_12      -0.1016017000
_diffrn_orient_matrix_UB_13      -0.0177142000
_diffrn_orient_matrix_UB_21      -0.0476144000
_diffrn_orient_matrix_UB_22      -0.0063542000
_diffrn_orient_matrix_UB_23      -0.1367664000
_diffrn_orient_matrix_UB_31      0.0708494000
_diffrn_orient_matrix_UB_32      0.0320180000
_diffrn_orient_matrix_UB_33      -0.0833044000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5189
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.428
_diffrn_reflns_theta_min         3.988
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             1060
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.213
_refine_diff_density_min         -1.074
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0736P)²+2.4066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1406
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2084
_reflns_number_total             2261
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0283_suppl.cif
_cod_data_source_block           rmm-20210702
_cod_original_formula_sum        'C14 H11 Cu0.50 N O2'
_cod_database_code               8104570
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_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.
;
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C14(H14)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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 1.460
_oxdiff_exptl_absorpt_empirical_full_min 0.802
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_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 0.26335(4) 0.7500 0.0649(3) Uani 1 2 d S T P . .
O1 O 0.62345(13) 0.25848(14) 0.6096(2) 0.0696(6) Uani 1 1 d . . . . .
O2 O 0.51926(10) 0.17467(15) 0.60237(19) 0.0625(5) Uani 1 1 d . . . . .
N1 N 0.55255(10) 0.36993(14) 0.85393(18) 0.0422(4) Uani 1 1 d . . . . .
C1 C 0.61861(13) 0.13741(16) 0.4426(2) 0.0433(5) Uani 1 1 d . . . . .
C2 C 0.69016(14) 0.1566(2) 0.3892(3) 0.0549(6) Uani 1 1 d . . . . .
H2 H 0.7182 0.2067 0.4240 0.066 Uiso 1 1 calc R U . . .
C3 C 0.72118(16) 0.1027(2) 0.2846(3) 0.0659(8) Uani 1 1 d . . . . .
H3 H 0.7697 0.1169 0.2492 0.079 Uiso 1 1 calc R U . . .
C4 C 0.6813(2) 0.0293(3) 0.2333(4) 0.0778(9) Uani 1 1 d . . . . .
H4 H 0.7022 -0.0073 0.1631 0.093 Uiso 1 1 calc R U . . .
C5 C 0.6099(3) 0.0094(3) 0.2857(5) 0.1088(17) Uani 1 1 d . . . . .
H5 H 0.5823 -0.0410 0.2511 0.131 Uiso 1 1 calc R U . . .
C6 C 0.5784(2) 0.0638(3) 0.3899(4) 0.0861(12) Uani 1 1 d . . . . .
H6 H 0.5295 0.0501 0.4241 0.103 Uiso 1 1 calc R U . . .
C7 C 0.58647(13) 0.19482(17) 0.5588(2) 0.0459(5) Uani 1 1 d . . . . .
C8 C 0.52918(12) 0.45348(16) 0.8047(2) 0.0406(5) Uani 1 1 d . . . . .
C9 C 0.55809(14) 0.53758(18) 0.8547(2) 0.0485(5) Uani 1 1 d . . . . .
C10 C 0.61643(15) 0.5328(2) 0.9587(3) 0.0564(6) Uani 1 1 d . . . . .
H10 H 0.6379 0.5868 0.9953 0.068 Uiso 1 1 calc R U . . .
C11 C 0.64104(14) 0.4488(2) 1.0048(3) 0.0577(7) Uani 1 1 d . . . . .
H11 H 0.6801 0.4456 1.0722 0.069 Uiso 1 1 calc R U . . .
C12 C 0.60824(13) 0.36659(19) 0.9520(2) 0.0496(6) Uani 1 1 d . . . . .
C13 C 0.63521(18) 0.2736(2) 1.0009(3) 0.0699(8) Uani 1 1 d . . . . .
H13A H 0.5916 0.2375 1.0297 0.105 Uiso 1 1 calc R U . . .
H13B H 0.6704 0.2810 1.0784 0.105 Uiso 1 1 calc R U . . .
H13C H 0.6610 0.2424 0.9259 0.105 Uiso 1 1 calc R U . . .
C14 C 0.52833(17) 0.62223(19) 0.8001(3) 0.0590(7) Uani 1 1 d . . . . .
H14 H 0.5478 0.6782 0.8331 0.071 Uiso 1 1 calc R U . . .
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'
N N 0.0311 0.0180 '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'
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
O2 Cu1 O2 97.24(13) . 2_656
O2 Cu1 N1 140.75(7) . .
O2 Cu1 N1 102.87(8) 2_656 .
O2 Cu1 N1 102.87(8) . 2_656
O2 Cu1 N1 140.75(7) 2_656 2_656
N1 Cu1 N1 82.09(11) . 2_656
C7 O2 Cu1 104.58(17) . .
C8 N1 Cu1 111.87(14) . .
C12 N1 Cu1 128.89(17) . .
C12 N1 C8 119.0(2) . .
C2 C1 C7 120.5(2) . .
C6 C1 C2 118.6(2) . .
C6 C1 C7 120.9(2) . .
C1 C2 H2 119.5 . .
C1 C2 C3 121.0(2) . .
C3 C2 H2 119.5 . .
C2 C3 H3 119.9 . .
C4 C3 C2 120.2(3) . .
C4 C3 H3 119.9 . .
C3 C4 H4 120.3 . .
C3 C4 C5 119.3(3) . .
C5 C4 H4 120.3 . .
C4 C5 H5 119.7 . .
C4 C5 C6 120.6(3) . .
C6 C5 H5 119.7 . .
C1 C6 C5 120.3(3) . .
C1 C6 H6 119.9 . .
C5 C6 H6 119.9 . .
O1 C7 O2 121.3(2) . .
O1 C7 C1 121.1(2) . .
O2 C7 C1 117.6(2) . .
N1 C8 C8 117.04(12) . 2_656
N1 C8 C9 123.5(2) . .
C9 C8 C8 119.50(14) . 2_656
C8 C9 C10 116.7(2) . .
C8 C9 C14 119.6(2) . .
C10 C9 C14 123.6(2) . .
C9 C10 H10 120.3 . .
C11 C10 C9 119.5(2) . .
C11 C10 H10 120.3 . .
C10 C11 H11 119.5 . .
C10 C11 C12 120.9(2) . .
C12 C11 H11 119.5 . .
N1 C12 C11 120.4(2) . .
N1 C12 C13 118.1(2) . .
C11 C12 C13 121.5(2) . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C9 C14 H14 119.6 . .
C14 C14 C9 120.82(15) 2_656 .
C14 C14 H14 119.6 2_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.937(2) .
Cu1 O2 1.937(2) 2_656
Cu1 N1 2.0408(19) 2_656
Cu1 N1 2.0407(19) .
O1 C7 1.218(3) .
O2 C7 1.273(3) .
N1 C8 1.355(3) .
N1 C12 1.338(3) .
C1 C2 1.372(3) .
C1 C6 1.364(4) .
C1 C7 1.498(3) .
C2 H2 0.9300 .
C2 C3 1.380(4) .
C3 H3 0.9300 .
C3 C4 1.355(5) .
C4 H4 0.9300 .
C4 C5 1.367(5) .
C5 H5 0.9300 .
C5 C6 1.385(5) .
C6 H6 0.9300 .
C8 C8 1.447(4) 2_656
C8 C9 1.396(3) .
C9 C10 1.411(4) .
C9 C14 1.424(4) .
C10 H10 0.9300 .
C10 C11 1.358(4) .
C11 H11 0.9300 .
C11 C12 1.407(4) .
C12 C13 1.495(4) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 C14 1.363(6) 2_656
C14 H14 0.9300 .
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 O2 C7 O1 -0.2(3) . . . .
Cu1 O2 C7 C1 179.84(16) . . . .
Cu1 N1 C8 C8 2.5(3) . . . 2_656
Cu1 N1 C8 C9 -177.90(16) . . . .
Cu1 N1 C12 C11 175.55(16) . . . .
Cu1 N1 C12 C13 -3.2(3) . . . .
N1 C8 C9 C10 2.1(3) . . . .
N1 C8 C9 C14 -177.9(2) . . . .
C1 C2 C3 C4 -0.3(5) . . . .
C2 C1 C6 C5 0.7(6) . . . .
C2 C1 C7 O1 -1.2(4) . . . .
C2 C1 C7 O2 178.8(2) . . . .
C2 C3 C4 C5 0.3(6) . . . .
C3 C4 C5 C6 0.2(8) . . . .
C4 C5 C6 C1 -0.7(8) . . . .
C6 C1 C2 C3 -0.1(5) . . . .
C6 C1 C7 O1 177.3(3) . . . .
C6 C1 C7 O2 -2.7(4) . . . .
C7 C1 C2 C3 178.3(3) . . . .
C7 C1 C6 C5 -177.8(4) . . . .
C8 N1 C12 C11 1.1(3) . . . .
C8 N1 C12 C13 -177.7(2) . . . .
C8 C8 C9 C10 -178.3(2) 2_656 . . .
C8 C8 C9 C14 1.7(4) 2_656 . . .
C8 C9 C10 C11 -0.3(3) . . . .
C8 C9 C14 C14 0.3(4) . . . 2_656
C9 C10 C11 C12 -1.1(4) . . . .
C10 C9 C14 C14 -179.8(3) . . . 2_656
C10 C11 C12 N1 0.7(4) . . . .
C10 C11 C12 C13 179.5(2) . . . .
C12 N1 C8 C8 177.8(2) . . . 2_656
C12 N1 C8 C9 -2.5(3) . . . .
C14 C9 C10 C11 179.8(2) . . . .
