#------------------------------------------------------------------------------
#$Date: 2019-11-08 03:32:13 +0200 (Fri, 08 Nov 2019) $
#$Revision: 225096 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/69/7156999.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_7156999
loop_
_publ_author_name
'Kirillova, Marina V.'
'Fernandes, Tiago A.'
'André, Vânia'
'Kirillov, Alexander M.'
_publ_section_title
;
 Mild C-H functionalization of alkanes catalyzed by bioinspired copper(ii)
 cores.
;
_journal_issue                   33
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7706
_journal_page_last               7714
_journal_paper_doi               10.1039/c9ob01442j
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C30 H44 Cu2 N2 O8'
_chemical_formula_weight         687.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-06-24 deposited with the CCDC.    2019-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.803(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.608(2)
_cell_length_b                   11.434(4)
_cell_length_c                   16.771(4)
_cell_measurement_reflns_used    5751
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.649
_cell_measurement_theta_min      2.175
_cell_volume                     3128.3(14)
_computing_cell_refinement       'BRUKER SMART (Bruker, 2005)'
_computing_data_collection       'BRUKER SMART (Bruker, 2005)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2005)'
_computing_molecular_graphics    'ORTEP 3.2 (Farrugia, 1997) and Mercury 2.2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR 97 (Altomare et al, 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1301
_diffrn_reflns_av_unetI/netI     0.0913
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25910
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         25.649
_diffrn_reflns_theta_min         2.175
_exptl_absorpt_coefficient_mu    1.411
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker,2005)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.910
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5751
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      0.911
_refine_ls_R_factor_all          0.1286
_refine_ls_R_factor_gt           0.0574
_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)+(0.0917P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1642
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3113
_reflns_number_total             5751
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ob01442j2.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7156997--7156999.cif.
;
_cod_database_code               7156999
_shelx_shelxl_version_number     2014/7
_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_min   0.872
_shelx_estimated_absorpt_t_max   0.920
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.1780(3) -0.0463(5) 0.0116(3) 0.0437(13) Uani 1 1 d . .
C2 C 0.1931(3) -0.0245(5) -0.0714(3) 0.0394(12) Uani 1 1 d . .
C3 C 0.2102(4) 0.0869(5) -0.0947(3) 0.0530(15) Uani 1 1 d . .
H3 H 0.2100 0.1489 -0.0589 0.064 Uiso 1 1 calc R U
C7 C 0.1923(3) -0.1145(5) -0.1256(3) 0.0426(13) Uani 1 1 d . .
H7 H 0.1806 -0.1900 -0.1107 0.051 Uiso 1 1 calc R U
C13 C 0.0725(4) 0.2660(6) 0.1327(5) 0.076(2) Uani 1 1 d . .
H13A H 0.0794 0.2985 0.1870 0.091 Uiso 1 1 calc R U
H13B H 0.1267 0.2523 0.1209 0.091 Uiso 1 1 calc R U
C14 C 0.0303(6) 0.3524(8) 0.0749(6) 0.123(4) Uani 1 1 d D .
H14A H -0.0253 0.3615 0.0841 0.148 Uiso 1 1 calc R U
H14B H 0.0577 0.4272 0.0861 0.148 Uiso 1 1 calc R U
C15 C 0.0272(11) 0.3246(11) -0.0076(7) 0.197(7) Uani 1 1 d D .
H15A H 0.0816 0.3256 -0.0193 0.296 Uiso 1 1 calc R U
H15B H -0.0061 0.3811 -0.0411 0.296 Uiso 1 1 calc R U
H15C H 0.0039 0.2481 -0.0186 0.296 Uiso 1 1 calc R U
C19 C 0.5052(4) 0.1106(6) 0.3559(4) 0.0627(18) Uani 1 1 d . .
H19A H 0.5025 0.0739 0.4074 0.075 Uiso 1 1 calc R U
H19B H 0.5558 0.1550 0.3621 0.075 Uiso 1 1 calc R U
O1 O 0.1735(3) -0.1485(4) 0.0349(3) 0.0703(13) Uani 1 1 d . .
O6 O 0.4367(2) 0.1868(4) 0.3326(2) 0.0578(11) Uani 1 1 d . .
H6O H 0.4206 0.2094 0.3733 0.087 Uiso 1 1 calc R U
C22 C 0.4205(6) -0.3406(9) 0.4062(6) 0.129(3) Uani 1 1 d D U
H22A H 0.3842 -0.4071 0.3931 0.154 Uiso 1 1 calc R U
H22B H 0.4744 -0.3629 0.3970 0.154 Uiso 1 1 calc R U
C23 C 0.4249(10) -0.3121(15) 0.4816(7) 0.263(11) Uani 1 1 d D U
H23A H 0.3981 -0.2383 0.4848 0.394 Uiso 1 1 calc R U
H23B H 0.4813 -0.3059 0.5076 0.394 Uiso 1 1 calc R U
H23C H 0.3984 -0.3710 0.5084 0.394 Uiso 1 1 calc R U
H3O H 0.159(5) -0.167(8) 0.1349(15) 0.11(3) Uiso 1 1 d D .
C4 C 0.2279(4) 0.1074(5) -0.1712(3) 0.0601(17) Uani 1 1 d . .
H4 H 0.2394 0.1832 -0.1858 0.072 Uiso 1 1 calc R U
C5 C 0.2288(3) 0.0164(5) -0.2267(3) 0.0399(13) Uani 1 1 d . .
C6 C 0.2087(3) -0.0939(5) -0.2028(3) 0.0456(13) Uani 1 1 d . .
H6 H 0.2060 -0.1558 -0.2392 0.055 Uiso 1 1 calc R U
C8 C 0.0833(4) -0.1576(6) 0.1998(5) 0.074(2) Uani 1 1 d . .
H8A H 0.0823 -0.1595 0.2574 0.089 Uiso 1 1 calc R U
H8B H 0.0578 -0.2289 0.1759 0.089 Uiso 1 1 calc R U
C9 C 0.0343(4) -0.0550(6) 0.1624(4) 0.0631(18) Uani 1 1 d . .
H9A H 0.0258 -0.0622 0.1038 0.076 Uiso 1 1 calc R U
H9B H -0.0191 -0.0570 0.1780 0.076 Uiso 1 1 calc R U
C10 C 0.1580(3) 0.0596(7) 0.3267(3) 0.0588(18) Uani 1 1 d . .
H10A H 0.1643 0.1002 0.3783 0.071 Uiso 1 1 calc R U
H10B H 0.1611 -0.0239 0.3370 0.071 Uiso 1 1 calc R U
C11 C 0.0773(3) 0.0907(8) 0.2737(4) 0.071(2) Uani 1 1 d . .
H11A H 0.0337 0.0499 0.2934 0.085 Uiso 1 1 calc R U
H11B H 0.0679 0.1740 0.2782 0.085 Uiso 1 1 calc R U
C12 C 0.0286(3) 0.1505(6) 0.1314(4) 0.0590(17) Uani 1 1 d . .
H12A H -0.0244 0.1636 0.1464 0.071 Uiso 1 1 calc R U
H12B H 0.0188 0.1203 0.0764 0.071 Uiso 1 1 calc R U
C16 C 0.3646(4) -0.0105(7) 0.1489(4) 0.069(2) Uani 1 1 d . .
H16A H 0.4040 0.0445 0.1346 0.083 Uiso 1 1 calc R U
H16B H 0.3348 -0.0452 0.0993 0.083 Uiso 1 1 calc R U
C17 C 0.4086(4) -0.1044(7) 0.2031(4) 0.071(2) Uani 1 1 d . .
H17A H 0.3730 -0.1719 0.2023 0.085 Uiso 1 1 calc R U
H17B H 0.4570 -0.1286 0.1830 0.085 Uiso 1 1 calc R U
C18 C 0.5039(3) 0.0212(6) 0.2935(4) 0.0588(17) Uani 1 1 d . .
H18A H 0.5545 -0.0233 0.3052 0.071 Uiso 1 1 calc R U
H18B H 0.5015 0.0591 0.2413 0.071 Uiso 1 1 calc R U
C20 C 0.4570(4) -0.1589(6) 0.3462(4) 0.0691(19) Uani 1 1 d . U
H20A H 0.5011 -0.2025 0.3293 0.083 Uiso 1 1 calc R U
H20B H 0.4782 -0.1265 0.3994 0.083 Uiso 1 1 calc R U
C21 C 0.3893(6) -0.2408(9) 0.3528(7) 0.129(3) Uani 1 1 d D U
H21A H 0.3472 -0.2000 0.3748 0.154 Uiso 1 1 calc R U
H21B H 0.3649 -0.2696 0.2993 0.154 Uiso 1 1 calc R U
C24 C 0.3349(3) 0.0957(6) 0.4679(3) 0.0486(14) Uani 1 1 d . .
C25 C 0.3045(3) 0.0728(5) 0.5446(3) 0.0417(13) Uani 1 1 d . .
C26 C 0.2723(4) -0.0335(5) 0.5620(3) 0.0533(15) Uani 1 1 d . .
H26 H 0.2679 -0.0942 0.5245 0.064 Uiso 1 1 calc R U
C27 C 0.2467(4) -0.0499(5) 0.6343(3) 0.0538(15) Uani 1 1 d . .
H27 H 0.2239 -0.1216 0.6440 0.065 Uiso 1 1 calc R U
C28 C 0.2533(3) 0.0366(5) 0.6939(3) 0.0390(12) Uani 1 1 d . .
C29 C 0.2867(3) 0.1434(5) 0.6749(3) 0.0447(13) Uani 1 1 d . .
H29 H 0.2927 0.2037 0.7128 0.054 Uiso 1 1 calc R U
C30 C 0.3106(3) 0.1611(5) 0.6028(3) 0.0459(13) Uani 1 1 d . .
H30 H 0.3314 0.2337 0.5920 0.055 Uiso 1 1 calc R U
N1 N 0.0734(2) 0.0606(4) 0.1864(3) 0.0475(12) Uani 1 1 d . .
N2 N 0.4328(3) -0.0609(4) 0.2880(3) 0.0513(12) Uani 1 1 d . .
O2 O 0.1725(2) 0.0436(3) 0.0556(2) 0.0470(9) Uani 1 1 d . .
O3 O 0.1661(3) -0.1547(4) 0.1890(3) 0.0632(11) Uani 1 1 d D .
O4 O 0.2198(2) 0.0944(4) 0.2842(2) 0.0455(9) Uani 1 1 d . .
O5 O 0.3101(2) 0.0480(4) 0.1893(2) 0.0489(10) Uani 1 1 d . .
O7 O 0.3347(2) 0.0088(4) 0.4188(2) 0.0490(10) Uani 1 1 d . .
O8 O 0.3602(3) 0.1960(4) 0.4553(3) 0.0724(13) Uani 1 1 d . .
Cu1 Cu 0.19298(3) 0.04994(6) 0.17222(3) 0.0375(2) Uani 1 1 d . .
Cu2 Cu 0.33157(4) 0.03401(6) 0.30480(4) 0.0403(2) Uani 1 1 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'
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'
Cu Cu 0.3201 1.2651 '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_3
O1 C1 O2 124.1(5) .
O1 C1 C2 119.1(5) .
O2 C1 C2 116.8(5) .
C7 C2 C3 118.8(5) .
C7 C2 C1 121.0(5) .
C3 C2 C1 120.1(5) .
C2 C3 C4 120.6(5) .
C2 C7 C6 120.7(5) .
C14 C13 C12 114.3(6) .
C15 C14 C13 114.9(9) .
O6 C19 C18 109.1(5) .
C23 C22 C21 110.2(12) .
C3 C4 C5 121.3(6) .
C6 C5 C4 116.9(5) .
C6 C5 C28 121.6(5) 1_554
C4 C5 C28 121.4(5) 1_554
C5 C6 C7 121.6(5) .
O3 C8 C9 113.1(6) .
N1 C9 C8 114.0(5) .
O4 C10 C11 106.6(5) .
N1 C11 C10 113.3(5) .
N1 C12 C13 114.4(5) .
O5 C16 C17 109.5(5) .
N2 C17 C16 110.6(6) .
C19 C18 N2 112.8(5) .
C21 C20 N2 114.1(5) .
C22 C21 C20 110.3(8) .
O8 C24 O7 124.0(6) .
O8 C24 C25 119.0(5) .
O7 C24 C25 117.0(6) .
C26 C25 C30 118.0(5) .
C26 C25 C24 123.0(5) .
C30 C25 C24 119.0(5) .
C27 C26 C25 120.2(5) .
C26 C27 C28 122.8(6) .
C27 C28 C29 115.8(5) .
C27 C28 C5 122.4(5) 1_556
C29 C28 C5 121.8(5) 1_556
C30 C29 C28 121.8(5) .
C29 C30 C25 121.4(6) .
C12 N1 C11 112.0(5) .
C12 N1 C9 107.6(4) .
C11 N1 C9 113.8(5) .
C12 N1 Cu1 110.7(4) .
C11 N1 Cu1 105.2(3) .
C9 N1 Cu1 107.3(4) .
C17 N2 C20 111.4(5) .
C17 N2 C18 109.6(5) .
C20 N2 C18 108.5(4) .
C17 N2 Cu2 103.0(3) .
C20 N2 Cu2 115.7(4) .
C18 N2 Cu2 108.4(4) .
C1 O2 Cu1 126.8(3) .
C8 O3 Cu1 104.0(4) .
C10 O4 Cu1 111.3(3) .
C10 O4 Cu2 124.6(3) .
Cu1 O4 Cu2 96.82(16) .
C16 O5 Cu2 115.9(3) .
C16 O5 Cu1 131.8(4) .
Cu2 O5 Cu1 98.30(17) .
C24 O7 Cu2 121.0(4) .
O5 Cu1 O4 79.23(14) .
O5 Cu1 O2 97.62(16) .
O4 Cu1 O2 166.28(18) .
O5 Cu1 N1 164.75(17) .
O4 Cu1 N1 85.58(17) .
O2 Cu1 N1 97.47(17) .
O5 Cu1 O3 100.19(17) .
O4 Cu1 O3 99.07(16) .
O2 Cu1 O3 94.63(16) .
N1 Cu1 O3 80.75(18) .
O5 Cu1 Cu2 40.83(10) .
O4 Cu1 Cu2 42.03(10) .
O2 Cu1 Cu2 138.03(12) .
N1 Cu1 Cu2 124.35(13) .
O3 Cu1 Cu2 89.29(11) .
O5 Cu2 O7 170.21(16) .
O5 Cu2 O4 78.44(14) .
O7 Cu2 O4 94.40(16) .
O5 Cu2 N2 84.72(17) .
O7 Cu2 N2 100.70(18) .
O4 Cu2 N2 159.19(17) .
O5 Cu2 Cu1 40.87(11) .
O7 Cu2 Cu1 130.01(12) .
O4 Cu2 Cu1 41.14(10) .
N2 Cu2 Cu1 118.67(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.239(7) .
C1 O2 1.278(7) .
C1 C2 1.481(7) .
C2 C7 1.371(7) .
C2 C3 1.378(8) .
C3 C4 1.389(8) .
C7 C6 1.391(7) .
C13 C14 1.467(10) .
C13 C12 1.508(9) .
C14 C15 1.412(11) .
C19 O6 1.428(7) .
C19 C18 1.460(9) .
C22 C23 1.296(11) .
C22 C21 1.482(11) .
C4 C5 1.397(8) .
C5 C6 1.383(8) .
C5 C28 1.482(7) 1_554
C8 O3 1.420(8) .
C8 C9 1.496(9) .
C9 N1 1.495(8) .
C10 O4 1.413(7) .
C10 C11 1.506(8) .
C11 N1 1.494(8) .
C12 N1 1.484(7) .
C16 O5 1.398(7) .
C16 C17 1.505(10) .
C17 N2 1.491(8) .
C18 N2 1.498(7) .
C20 C21 1.484(11) .
C20 N2 1.491(8) .
C24 O8 1.252(8) .
C24 O7 1.289(7) .
C24 C25 1.491(8) .
C25 C26 1.381(8) .
C25 C30 1.396(8) .
C26 C27 1.372(8) .
C27 C28 1.396(7) .
C28 C29 1.403(8) .
C28 C5 1.482(7) 1_556
C29 C30 1.356(7) .
N1 Cu1 2.048(4) .
N2 Cu2 2.064(5) .
O2 Cu1 1.922(3) .
O3 Cu1 2.408(5) .
O4 Cu1 1.916(3) .
O4 Cu2 1.949(3) .
O5 Cu2 1.910(3) .
O5 Cu1 1.912(4) .
O7 Cu2 1.925(4) .
Cu1 Cu2 2.8908(9) .
