#------------------------------------------------------------------------------
#$Date: 2024-02-04 14:08:26 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289549 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/45/7714562.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_7714562
loop_
_publ_author_name
'Singh, Ovender'
'Singh, Anshu'
'Maji, Ankur'
'Chauhan, Rahul'
'Gupta, Puneet'
'Ghosh, Kaushik'
_publ_section_title
;
 Crystal structure of a phenoxyl radical complex relevant to the metal
 site of the galactose oxidase enzyme: A facile one-pot synthesis,
 evidence for hydrogen atom transfer and DNA cleavage via
 self-activation.
;
_journal_issue                   3
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              986
_journal_page_last               995
_journal_paper_doi               10.1039/d3dt03282e
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C31 H24 Cu N5 O2, Cl O4'
_chemical_formula_sum            'C31 H24 Cl Cu N5 O6'
_chemical_formula_weight         661.54
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-10-01
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-10-06 deposited with the CCDC.	2023-11-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.332(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2622(7)
_cell_length_b                   14.8135(7)
_cell_length_c                   17.2490(9)
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    119(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.25
_cell_volume                     3322.7(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      119.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            69356
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_min         2.084
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0577 before and 0.0447 after correction. The Ratio of minimum to maximum transmission is 0.9287. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'metallic dark green'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             1356
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         8204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0329
_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)+(0.0534P)²+1.9260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7500
_reflns_number_total             8204
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt03282e2.cif
_cod_data_source_block           kg_ovi1_rc_0535_0m_b
_cod_depositor_comments
'Adding full bibliography for 7714562--7714563.cif.'
_cod_database_code               7714562
_shelx_shelxl_version_number     2019/1
_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   0.968
_shelx_estimated_absorpt_t_min   0.852
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23),
  C24(H24), C25(H25), C28(H28), C29(H29), C30(H30), C31(H31)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.60650(2) 0.55247(2) 0.42341(2) 0.01592(6) Uani 1 1 d . . . . .
Cl1 Cl 0.79164(3) 0.51603(3) 0.27723(3) 0.02993(10) Uani 1 1 d . . . . .
O1 O 0.46696(8) 0.53699(7) 0.38657(7) 0.0207(2) Uani 1 1 d . . . . .
O2 O 0.44465(10) 0.86815(8) 0.28314(8) 0.0277(3) Uani 1 1 d . . . . .
H2 H 0.404(2) 0.8964(18) 0.2629(16) 0.042 Uiso 1 1 d R . . . .
O3 O 0.69538(10) 0.49174(9) 0.30089(8) 0.0311(3) Uani 1 1 d . . . . .
O4 O 0.84045(16) 0.58547(13) 0.32827(12) 0.0666(6) Uani 1 1 d . . . . .
O5 O 0.7714(2) 0.54423(14) 0.19721(11) 0.0686(6) Uani 1 1 d . . . . .
O6 O 0.85606(13) 0.43820(13) 0.28459(12) 0.0575(5) Uani 1 1 d . . . . .
N1 N 0.73023(9) 0.41525(8) 0.50502(8) 0.0198(3) Uani 1 1 d . . . . .
N2 N 0.63084(9) 0.42823(8) 0.46172(8) 0.0171(2) Uani 1 1 d . . . . .
N3 N 0.74231(9) 0.56542(8) 0.48054(8) 0.0167(2) Uani 1 1 d . . . . .
N4 N 0.63759(9) 0.68444(8) 0.39223(8) 0.0177(2) Uani 1 1 d . . . . .
N5 N 0.72703(10) 0.71334(8) 0.44432(8) 0.0193(2) Uani 1 1 d . . . . .
C1 C 0.76564(11) 0.32953(9) 0.53768(9) 0.0176(3) Uani 1 1 d . . . . .
C2 C 0.83896(11) 0.28340(10) 0.50576(9) 0.0198(3) Uani 1 1 d . . . . .
H2A H 0.863090 0.307312 0.461650 0.024 Uiso 1 1 calc R . . . .
C3 C 0.87671(12) 0.20152(11) 0.53929(10) 0.0230(3) Uani 1 1 d . . . . .
H3 H 0.928039 0.169908 0.518785 0.028 Uiso 1 1 calc R . . . .
C4 C 0.83946(13) 0.16626(10) 0.60243(10) 0.0245(3) Uani 1 1 d . . . . .
H4 H 0.865516 0.110520 0.625240 0.029 Uiso 1 1 calc R . . . .
C5 C 0.76431(13) 0.21180(11) 0.63264(11) 0.0271(3) Uani 1 1 d . . . . .
H5 H 0.738051 0.186376 0.675196 0.033 Uiso 1 1 calc R . . . .
C6 C 0.72708(12) 0.29462(11) 0.60093(10) 0.0229(3) Uani 1 1 d . . . . .
H6 H 0.676487 0.326569 0.622020 0.027 Uiso 1 1 calc R . . . .
C7 C 0.78794(11) 0.64614(9) 0.48458(9) 0.0173(3) Uani 1 1 d . . . . .
C8 C 0.88776(12) 0.65787(10) 0.52714(9) 0.0207(3) Uani 1 1 d . . . . .
H8 H 0.920162 0.715345 0.531836 0.025 Uiso 1 1 calc R . . . .
C9 C 0.93766(11) 0.58152(11) 0.56239(9) 0.0209(3) Uani 1 1 d . . . . .
H9 H 1.006030 0.587327 0.591475 0.025 Uiso 1 1 calc R . . . .
C10 C 0.89132(11) 0.49673(10) 0.55672(9) 0.0199(3) Uani 1 1 d . . . . .
H10 H 0.926809 0.444843 0.580292 0.024 Uiso 1 1 calc R . . . .
C11 C 0.79035(11) 0.49182(10) 0.51479(9) 0.0172(3) Uani 1 1 d . . . . .
C12 C 0.56602(11) 0.36244(10) 0.44792(9) 0.0187(3) Uani 1 1 d . . . . .
H12 H 0.587217 0.304219 0.467801 0.022 Uiso 1 1 calc R . . . .
C13 C 0.46283(11) 0.37371(10) 0.40359(9) 0.0181(3) Uani 1 1 d . . . . .
C14 C 0.40357(12) 0.29412(11) 0.38677(10) 0.0225(3) Uani 1 1 d . . . . .
H14 H 0.432955 0.237889 0.405729 0.027 Uiso 1 1 calc R . . . .
C15 C 0.30467(13) 0.29592(11) 0.34376(10) 0.0257(3) Uani 1 1 d . . . . .
H15 H 0.266219 0.241757 0.332538 0.031 Uiso 1 1 calc R . . . .
C16 C 0.26179(12) 0.37929(12) 0.31682(10) 0.0245(3) Uani 1 1 d . . . . .
H16 H 0.193100 0.381602 0.287791 0.029 Uiso 1 1 calc R . . . .
C17 C 0.31757(12) 0.45807(11) 0.33172(10) 0.0229(3) Uani 1 1 d . . . . .
H17 H 0.286574 0.513545 0.312276 0.028 Uiso 1 1 calc R . . . .
C18 C 0.41949(11) 0.45841(10) 0.37510(9) 0.0181(3) Uani 1 1 d . . . . .
C19 C 0.76916(12) 0.80194(10) 0.43953(9) 0.0209(3) Uani 1 1 d . . . . .
C20 C 0.74580(19) 0.86877(13) 0.48916(13) 0.0403(5) Uani 1 1 d . . . . .
H20 H 0.700337 0.856810 0.524164 0.048 Uiso 1 1 calc R . . . .
C21 C 0.7898(3) 0.95366(14) 0.48708(16) 0.0548(7) Uani 1 1 d . . . . .
H21 H 0.773660 1.000476 0.520259 0.066 Uiso 1 1 calc R . . . .
C22 C 0.85739(18) 0.97012(13) 0.43656(13) 0.0407(5) Uani 1 1 d . . . . .
H22 H 0.888226 1.027921 0.435841 0.049 Uiso 1 1 calc R . . . .
C23 C 0.87992(14) 0.90244(12) 0.38719(12) 0.0308(4) Uani 1 1 d . . . . .
H23 H 0.926229 0.913804 0.352719 0.037 Uiso 1 1 calc R . . . .
C24 C 0.83478(13) 0.81797(11) 0.38814(11) 0.0254(3) Uani 1 1 d . . . . .
H24 H 0.848949 0.771656 0.353716 0.031 Uiso 1 1 calc R . . . .
C25 C 0.58971(11) 0.74188(10) 0.34188(9) 0.0196(3) Uani 1 1 d . . . . .
H25 H 0.612774 0.802729 0.344845 0.024 Uiso 1 1 calc R . . . .
C26 C 0.50165(11) 0.71734(10) 0.28056(9) 0.0197(3) Uani 1 1 d . . . . .
C27 C 0.42887(12) 0.78436(10) 0.25119(10) 0.0214(3) Uani 1 1 d . . . . .
C28 C 0.34343(12) 0.76306(12) 0.19294(10) 0.0256(3) Uani 1 1 d . . . . .
H28 H 0.293547 0.808069 0.174208 0.031 Uiso 1 1 calc R . . . .
C29 C 0.33122(14) 0.67660(13) 0.16245(10) 0.0299(4) Uani 1 1 d . . . . .
H29 H 0.272096 0.662046 0.123677 0.036 Uiso 1 1 calc R . . . .
C30 C 0.40499(15) 0.61075(12) 0.18820(11) 0.0313(4) Uani 1 1 d . . . . .
H30 H 0.397318 0.551863 0.166008 0.038 Uiso 1 1 calc R . . . .
C31 C 0.48970(13) 0.63143(11) 0.24636(10) 0.0252(3) Uani 1 1 d . . . . .
H31 H 0.540445 0.586562 0.263270 0.030 Uiso 1 1 calc R . . . .
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'
Cl Cl 0.1484 0.1585 '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'
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'
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 N2 94.98(5) . . ?
O1 Cu1 N3 168.83(5) . . ?
O1 Cu1 N4 105.21(5) . . ?
N2 Cu1 N4 159.56(5) . . ?
N3 Cu1 N2 80.92(5) . . ?
N3 Cu1 N4 79.80(5) . . ?
O4 Cl1 O3 108.75(8) . . ?
O4 Cl1 O6 109.72(13) . . ?
O5 Cl1 O3 109.68(12) . . ?
O5 Cl1 O4 111.43(13) . . ?
O5 Cl1 O6 108.69(13) . . ?
O6 Cl1 O3 108.51(10) . . ?
C18 O1 Cu1 125.22(9) . . ?
N2 N1 C1 122.40(11) . . ?
C11 N1 N2 114.54(12) . . ?
C11 N1 C1 123.05(12) . . ?
N1 N2 Cu1 112.68(9) . . ?
C12 N2 Cu1 125.96(10) . . ?
C12 N2 N1 121.33(12) . . ?
C7 N3 Cu1 119.65(10) . . ?
C7 N3 C11 122.28(13) . . ?
C11 N3 Cu1 118.06(10) . . ?
N5 N4 Cu1 107.73(9) . . ?
C25 N4 Cu1 133.96(10) . . ?
C25 N4 N5 118.10(12) . . ?
N4 N5 C19 122.04(12) . . ?
C7 N5 N4 116.02(12) . . ?
C7 N5 C19 119.51(12) . . ?
C2 C1 N1 118.82(13) . . ?
C2 C1 C6 121.46(14) . . ?
C6 C1 N1 119.72(14) . . ?
C1 C2 C3 119.10(14) . . ?
C4 C3 C2 120.03(15) . . ?
C3 C4 C5 120.40(14) . . ?
C4 C5 C6 120.41(15) . . ?
C1 C6 C5 118.57(15) . . ?
N3 C7 N5 113.89(13) . . ?
N3 C7 C8 120.87(13) . . ?
N5 C7 C8 125.24(13) . . ?
C9 C8 C7 116.81(13) . . ?
C8 C9 C10 122.53(14) . . ?
C11 C10 C9 116.69(14) . . ?
N1 C11 C10 125.49(13) . . ?
N3 C11 N1 113.73(12) . . ?
N3 C11 C10 120.77(13) . . ?
N2 C12 C13 122.65(13) . . ?
C14 C13 C12 116.35(13) . . ?
C14 C13 C18 119.49(13) . . ?
C18 C13 C12 124.15(13) . . ?
C15 C14 C13 121.81(15) . . ?
C14 C15 C16 118.59(14) . . ?
C17 C16 C15 121.11(14) . . ?
C16 C17 C18 121.67(15) . . ?
O1 C18 C13 125.18(13) . . ?
O1 C18 C17 117.50(13) . . ?
C17 C18 C13 117.31(13) . . ?
C20 C19 N5 118.81(15) . . ?
C24 C19 N5 119.75(14) . . ?
C24 C19 C20 121.39(15) . . ?
C19 C20 C21 119.03(19) . . ?
C22 C21 C20 120.1(2) . . ?
C23 C22 C21 120.15(17) . . ?
C22 C23 C24 119.95(18) . . ?
C19 C24 C23 119.38(16) . . ?
N4 C25 C26 122.79(13) . . ?
C27 C26 C25 118.67(14) . . ?
C31 C26 C25 122.73(14) . . ?
C31 C26 C27 118.49(15) . . ?
O2 C27 C26 117.29(14) . . ?
O2 C27 C28 122.53(14) . . ?
C28 C27 C26 120.16(15) . . ?
C29 C28 C27 120.10(15) . . ?
C28 C29 C30 120.39(16) . . ?
C31 C30 C29 119.70(16) . . ?
C30 C31 C26 121.01(15) . . ?
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 1.8491(11) . ?
Cu1 N2 1.9607(12) . ?
Cu1 N3 1.8853(13) . ?
Cu1 N4 2.0900(12) . ?
Cl1 O3 1.4597(13) . ?
Cl1 O4 1.4241(15) . ?
Cl1 O5 1.4165(19) . ?
Cl1 O6 1.4257(17) . ?
O1 C18 1.3196(18) . ?
O2 C27 1.357(2) . ?
N1 N2 1.3947(16) . ?
N1 C1 1.4305(18) . ?
N1 C11 1.3776(18) . ?
N2 C12 1.2905(19) . ?
N3 C7 1.3358(18) . ?
N3 C11 1.3400(18) . ?
N4 N5 1.4067(17) . ?
N4 C25 1.2903(19) . ?
N5 C7 1.3802(19) . ?
N5 C19 1.4353(18) . ?
C1 C2 1.388(2) . ?
C1 C6 1.392(2) . ?
C2 C3 1.394(2) . ?
C3 C4 1.384(2) . ?
C4 C5 1.387(2) . ?
C5 C6 1.393(2) . ?
C7 C8 1.393(2) . ?
C8 C9 1.389(2) . ?
C9 C10 1.393(2) . ?
C10 C11 1.393(2) . ?
C12 C13 1.440(2) . ?
C13 C14 1.415(2) . ?
C13 C18 1.427(2) . ?
C14 C15 1.375(2) . ?
C15 C16 1.400(2) . ?
C16 C17 1.379(2) . ?
C17 C18 1.411(2) . ?
C19 C20 1.383(2) . ?
C19 C24 1.379(2) . ?
C20 C21 1.390(3) . ?
C21 C22 1.389(3) . ?
C22 C23 1.386(3) . ?
C23 C24 1.389(2) . ?
C25 C26 1.459(2) . ?
C26 C27 1.408(2) . ?
C26 C31 1.399(2) . ?
C27 C28 1.395(2) . ?
C28 C29 1.382(3) . ?
C29 C30 1.391(3) . ?
C30 C31 1.385(2) . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.481 0.250 234.7 98.7 ?
2 0.000 -0.638 0.750 234.7 98.6 ?
3 0.500 0.500 1.000 119.1 49.5 ?
4 0.500 1.000 0.500 119.1 49.5 ?
