#------------------------------------------------------------------------------
#$Date: 2024-09-21 00:20:42 +0200 (Sat 21 de Sep de 2024) $
#$Revision: 294826 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/26/1572623.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_1572623
loop_
_publ_author_name
'Chen, Ting-An'
'Staples, Richard J.'
'Warren, Timothy H.'
_publ_section_title
;
 Copper Catalyzed Benzylic sp3 C-H Alkenylation
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D4SC03430A
_journal_year                    2024
_chemical_formula_moiety         'C24 H26 B Cl4 Cu N2 O2'
_chemical_formula_sum            'C24 H26 B Cl4 Cu N2 O2'
_chemical_formula_weight         590.62
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-26
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-26 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.3650(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.81870(10)
_cell_length_b                   13.46770(10)
_cell_length_c                   20.27360(10)
_cell_measurement_reflns_used    30230
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      79.8350
_cell_measurement_theta_min      3.9540
_cell_volume                     2608.28(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  28.00   0.50    0.05    --  -47.10  19.00 150.00  134
  2  ω    -70.00  16.00   0.50    0.05    --  -47.10  77.00  90.00  172
  3  ω    -47.00  26.00   0.50    0.05    --  -47.10  37.00   0.00  146
  4  ω    -47.00  26.00   0.50    0.05    --  -47.10  37.00-120.00  146
  5  ω     35.00 120.00   0.50    0.05    --   47.10  37.00-180.00  170
  6  ω     35.00 119.00   0.50    0.05    --   47.10  45.00-103.64  168
  7  ω     35.00 119.00   0.50    0.05    --   47.10  45.00  29.78  168
  8  ω     35.00 120.00   0.50    0.05    --   47.10  37.00  90.00  170
  9  ω     34.00 119.00   0.50    0.05    --   47.10  47.00 122.69  170
 10  ω     35.00 119.00   0.50    0.05    --   47.10  45.00 -16.37  168
 11  ω    110.00 178.00   0.50    0.20    --  113.25  77.00-180.00  136
 12  ω    101.00 178.00   0.50    0.20    --  113.25  45.00-180.00  154
 13  ω    106.00 178.00   0.50    0.20    --  113.25  61.00-150.00  144
 14  ω    101.00 178.00   0.50    0.20    --  113.25  45.00-120.00  154
 15  ω    101.00 178.00   0.50    0.20    --  113.25  45.00 -90.00  154
 16  ω    101.00 178.00   0.50    0.20    --  113.25  30.00 -30.00  154
 17  ω    101.00 178.00   0.50    0.20    --  113.25  30.00  30.00  154
 18  ω    101.00 178.00   0.50    0.20    --  113.25  45.00  90.00  154
 19  ω    101.00 178.00   0.50    0.20    --  113.25  30.00 120.00  154
 20  ω    100.00 178.00   0.50    0.20    --  113.25  15.00-180.00  156
 21  ω     42.00 104.00   0.50    0.20    --  113.25 -94.00-180.00  124
 22  ω     36.00  93.00   0.50    0.05    --   47.10-125.00-180.00  114
 23  ω     44.00 108.00   0.50    0.20    --  113.25-125.00-180.00  128
 24  ω     44.00 108.00   0.50    0.20    --  113.25-125.00 -30.00  128
 25  ω     44.00 108.00   0.50    0.20    --  113.25-125.00  30.00  128
 26  ω     44.00 108.00   0.50    0.20    --  113.25-125.00   0.00  128
 27  ω     43.00 105.00   0.50    0.20    --  113.25-105.00 -18.24  124
 28  ω     44.00 108.00   0.50    0.20    --  113.25-125.00  60.00  128
 29  ω     43.00 104.00   0.50    0.20    --  113.25 -96.00 141.83  122
 30  ω     44.00 108.00   0.50    0.20    --  113.25-125.00 150.00  128
 31  ω     42.00 104.00   0.50    0.20    --  113.25 -94.00 150.00  124
 32  ω     42.00 104.00   0.50    0.20    --  113.25 -94.00  90.00  124
 33  ω     42.00 104.00   0.50    0.20    --  113.25 -94.00  30.00  124
 34  ω     42.00 104.00   0.50    0.20    --  113.25 -94.00  60.00  124
 35  ω     42.00 104.00   0.50    0.20    --  113.25 -94.00 -90.00  124
 36  ω     42.00 104.00   0.50    0.20    --  113.25 -94.00-120.00  124
 37  ω     42.00 104.00   0.50    0.20    --  113.25 -94.00-150.00  124
 38  ω     42.00  94.00   0.50    0.20    --  113.25 -77.00-120.00  104
 39  ω     42.00  94.00   0.50    0.20    --  113.25 -77.00-180.00  104
 40  ω     42.00  94.00   0.50    0.20    --  113.25 -77.00  30.00  104
 41  ω     42.00  94.00   0.50    0.20    --  113.25 -77.00  60.00  104
 42  ω     42.00  69.00   0.50    0.20    --  113.25 -61.00  90.00   54
 43  ω     42.00  94.00   0.50    0.20    --  113.25 -77.00 150.00  104
 44  ω     42.00  69.00   0.50    0.20    --  113.25 -61.00   0.00   54
 45  ω     42.00  69.00   0.50    0.20    --  113.25 -61.00 -60.00   54
 46  ω    -70.00 -19.00   0.50    0.20    --  -91.75  61.00 -90.00  102
 47  ω    -70.00 -19.00   0.50    0.20    --  -91.75  61.00   0.00  102
 48  ω    -70.00 -19.00   0.50    0.20    --  -91.75  61.00  60.00  102
;
_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      0.1274593000
_diffrn_orient_matrix_UB_12      0.0577369000
_diffrn_orient_matrix_UB_13      -0.0121024000
_diffrn_orient_matrix_UB_21      0.0465136000
_diffrn_orient_matrix_UB_22      -0.0922363000
_diffrn_orient_matrix_UB_23      -0.0340604000
_diffrn_orient_matrix_UB_31      -0.0871943000
_diffrn_orient_matrix_UB_32      0.0352274000
_diffrn_orient_matrix_UB_33      -0.0692354000
_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  0.0502
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            53838
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.380
_diffrn_reflns_theta_min         3.975
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    5.153
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.382
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1208
_exptl_crystal_recrystallization_method 'used as recieved'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5673
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0305
_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)+(0.0387P)²+1.9234P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0813
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5318
_reflns_number_total             5673
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc03430a2.cif
_cod_data_source_block           tc_14_cl2nncu_prenylbester
_cod_database_code               1572623
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C24H26BCl4CuN2O2
_chemical_oxdiff_usercomment     PhF/C5
_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   0.861
_shelx_estimated_absorpt_t_min   0.384
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C16(H16), C17(H17), C18(H18), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id TC-14-(Cl2NNCu)-PrenylBester
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.281
_oxdiff_exptl_absorpt_empirical_full_min 0.774
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 0.67847(2) 0.70672(2) 0.63453(2) 0.01542(7) Uani 1 1 d . . . . .
Cl1 Cl 1.07079(5) 0.69570(4) 0.74736(2) 0.03609(13) Uani 1 1 d . . . . .
Cl2 Cl 0.61342(6) 0.46226(4) 0.71568(3) 0.04053(13) Uani 1 1 d . . . . .
Cl3 Cl 0.79528(4) 0.90361(3) 0.54136(2) 0.02349(10) Uani 1 1 d . . . . .
Cl4 Cl 0.40760(4) 0.61750(3) 0.45672(2) 0.02484(10) Uani 1 1 d . . . . .
O1 O 0.34303(13) 0.68612(9) 0.63064(7) 0.0244(3) Uani 1 1 d . . . . .
O2 O 0.31881(12) 0.83221(9) 0.56083(6) 0.0213(2) Uani 1 1 d . . . . .
N1 N 0.80790(14) 0.60012(10) 0.66700(7) 0.0168(3) Uani 1 1 d . . . . .
N2 N 0.68115(14) 0.69693(10) 0.53896(7) 0.0159(3) Uani 1 1 d . . . . .
C1 C 0.54238(17) 0.81185(12) 0.64654(8) 0.0185(3) Uani 1 1 d . . . . .
H1 H 0.563983 0.878872 0.630320 0.022 Uiso 1 1 calc R U . . .
C2 C 0.62144(18) 0.78816(13) 0.71119(8) 0.0199(3) Uani 1 1 d . . . . .
C4 C 0.20486(19) 0.65387(14) 0.59665(10) 0.0274(4) Uani 1 1 d . . . . .
H4A H 0.163709 0.614134 0.628264 0.033 Uiso 1 1 calc R U . . .
H4B H 0.210900 0.611082 0.557719 0.033 Uiso 1 1 calc R U . . .
C5 C 0.11145(19) 0.74210(15) 0.57172(10) 0.0286(4) Uani 1 1 d . . . . .
H5A H 0.018534 0.718823 0.546202 0.034 Uiso 1 1 calc R U . . .
H5B H 0.098159 0.781929 0.610795 0.034 Uiso 1 1 calc R U . . .
C6 C 0.17859(19) 0.80499(15) 0.52646(9) 0.0259(4) Uani 1 1 d . . . . .
H6A H 0.181012 0.767545 0.484729 0.031 Uiso 1 1 calc R U . . .
H6B H 0.122144 0.865734 0.513147 0.031 Uiso 1 1 calc R U . . .
C7 C 0.7432(2) 0.85380(14) 0.74379(9) 0.0272(4) Uani 1 1 d . . . . .
H7A H 0.817058 0.813238 0.772056 0.041 Uiso 1 1 calc R U . . .
H7B H 0.711681 0.903904 0.772007 0.041 Uiso 1 1 calc R U . . .
H7C H 0.779906 0.886837 0.708447 0.041 Uiso 1 1 calc R U . . .
C8 C 0.5677(2) 0.72512(14) 0.76105(9) 0.0253(4) Uani 1 1 d . . . . .
H8A H 0.505650 0.673513 0.736584 0.038 Uiso 1 1 calc R U . . .
H8B H 0.515654 0.766866 0.786316 0.038 Uiso 1 1 calc R U . . .
H8C H 0.646762 0.693956 0.792700 0.038 Uiso 1 1 calc R U . . .
C9 C 0.94638(19) 0.45284(14) 0.65490(9) 0.0252(4) Uani 1 1 d . . . . .
H9A H 1.032374 0.475530 0.686153 0.038 Uiso 1 1 calc R U . . .
H9B H 0.970429 0.414510 0.618096 0.038 Uiso 1 1 calc R U . . .
H9C H 0.893062 0.410892 0.679408 0.038 Uiso 1 1 calc R U . . .
C10 C 0.85912(16) 0.54144(12) 0.62573(8) 0.0174(3) Uani 1 1 d . . . . .
C11 C 0.83673(17) 0.55668(12) 0.55548(8) 0.0180(3) Uani 1 1 d . . . . .
H11 H 0.882891 0.511238 0.532162 0.022 Uiso 1 1 calc R U . . .
C12 C 0.75596(17) 0.62943(12) 0.51496(8) 0.0171(3) Uani 1 1 d . . . . .
C13 C 0.75795(19) 0.62968(14) 0.44048(9) 0.0245(4) Uani 1 1 d . . . . .
H13A H 0.665680 0.610182 0.413462 0.037 Uiso 1 1 calc R U . . .
H13B H 0.828608 0.582569 0.432626 0.037 Uiso 1 1 calc R U . . .
H13C H 0.780852 0.696466 0.427167 0.037 Uiso 1 1 calc R U . . .
C14 C 0.84271(18) 0.57848(13) 0.73710(8) 0.0205(3) Uani 1 1 d . . . . .
C15 C 0.95894(19) 0.62111(16) 0.78101(9) 0.0268(4) Uani 1 1 d . . . . .
C16 C 0.9896(2) 0.6053(2) 0.85046(10) 0.0392(5) Uani 1 1 d . . . . .
H16 H 1.069395 0.635408 0.878933 0.047 Uiso 1 1 calc R U . . .
C17 C 0.9023(2) 0.5453(2) 0.87772(10) 0.0411(5) Uani 1 1 d . . . . .
H17 H 0.921849 0.534578 0.925300 0.049 Uiso 1 1 calc R U . . .
C18 C 0.7879(3) 0.50101(16) 0.83657(11) 0.0365(5) Uani 1 1 d . . . . .
H18 H 0.728631 0.459436 0.855507 0.044 Uiso 1 1 calc R U . . .
C19 C 0.7591(2) 0.51725(14) 0.76718(10) 0.0271(4) Uani 1 1 d . . . . .
C20 C 0.59945(16) 0.76412(12) 0.49247(8) 0.0162(3) Uani 1 1 d . . . . .
C21 C 0.63923(17) 0.86312(13) 0.48834(8) 0.0185(3) Uani 1 1 d . . . . .
C22 C 0.55981(19) 0.93083(13) 0.44373(9) 0.0223(3) Uani 1 1 d . . . . .
H22 H 0.589480 0.997831 0.442662 0.027 Uiso 1 1 calc R U . . .
C23 C 0.43624(19) 0.89874(14) 0.40075(9) 0.0240(4) Uani 1 1 d . . . . .
H23 H 0.382179 0.943665 0.369084 0.029 Uiso 1 1 calc R U . . .
C24 C 0.39127(18) 0.80167(14) 0.40374(9) 0.0223(3) Uani 1 1 d . . . . .
H24 H 0.306686 0.779900 0.374322 0.027 Uiso 1 1 calc R U . . .
C25 C 0.47100(17) 0.73659(13) 0.45013(8) 0.0190(3) Uani 1 1 d . . . . .
B1 B 0.3934(2) 0.77287(14) 0.61136(9) 0.0188(4) 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 0.0181 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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 7 -6 0.0782
-1 -7 -7 0.0497
2 -7 7 0.0454
1 7 7 0.0859
-1 0 0 0.0158
1 0 0 0.0158
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
N1 Cu1 N2 97.45(6) . . ?
N1 Cu1 C1 153.01(6) . . ?
N1 Cu1 C2 114.01(6) . . ?
N2 Cu1 C1 109.39(6) . . ?
N2 Cu1 C2 147.77(6) . . ?
C1 Cu1 C2 39.97(7) . . ?
B1 O1 C4 119.12(14) . . ?
B1 O2 C6 119.97(14) . . ?
C10 N1 Cu1 122.82(11) . . ?
C10 N1 C14 118.10(14) . . ?
C14 N1 Cu1 118.93(11) . . ?
C12 N2 Cu1 123.08(11) . . ?
C12 N2 C20 118.02(13) . . ?
C20 N2 Cu1 118.90(10) . . ?
Cu1 C1 H1 113.6 . . ?
C2 C1 Cu1 73.18(10) . . ?
C2 C1 H1 113.6 . . ?
C2 C1 B1 127.58(16) . . ?
B1 C1 Cu1 106.73(11) . . ?
B1 C1 H1 113.6 . . ?
C1 C2 Cu1 66.85(9) . . ?
C1 C2 C7 119.25(16) . . ?
C1 C2 C8 123.61(16) . . ?
C7 C2 Cu1 108.21(12) . . ?
C8 C2 Cu1 113.62(12) . . ?
C8 C2 C7 113.64(15) . . ?
O1 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
O1 C4 C5 110.73(15) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C4 C5 H5A 109.9 . . ?
C4 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C6 C5 C4 109.12(16) . . ?
C6 C5 H5A 109.9 . . ?
C6 C5 H5B 109.9 . . ?
O2 C6 C5 110.63(15) . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
N1 C10 C9 119.10(15) . . ?
N1 C10 C11 123.85(15) . . ?
C11 C10 C9 117.05(15) . . ?
C10 C11 H11 115.4 . . ?
C12 C11 C10 129.14(15) . . ?
C12 C11 H11 115.4 . . ?
N2 C12 C11 123.33(15) . . ?
N2 C12 C13 119.92(15) . . ?
C11 C12 C13 116.75(14) . . ?
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 . . ?
C15 C14 N1 121.86(16) . . ?
C15 C14 C19 116.07(16) . . ?
C19 C14 N1 122.00(16) . . ?
C14 C15 Cl1 118.93(13) . . ?
C16 C15 Cl1 118.57(16) . . ?
C16 C15 C14 122.50(19) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.1(2) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.48(19) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.7(2) . . ?
C19 C18 H18 120.2 . . ?
C14 C19 Cl2 118.42(14) . . ?
C18 C19 Cl2 119.41(16) . . ?
C18 C19 C14 122.2(2) . . ?
C21 C20 N2 121.81(14) . . ?
C21 C20 C25 116.11(15) . . ?
C25 C20 N2 122.02(15) . . ?
C20 C21 Cl3 118.65(13) . . ?
C22 C21 Cl3 118.49(13) . . ?
C22 C21 C20 122.86(16) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 C21 118.78(16) . . ?
C23 C22 H22 120.6 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.47(16) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.35(16) . . ?
C25 C24 H24 120.3 . . ?
C20 C25 Cl4 119.00(13) . . ?
C24 C25 Cl4 118.65(13) . . ?
C24 C25 C20 122.34(16) . . ?
O1 B1 O2 123.25(16) . . ?
O1 B1 C1 121.44(16) . . ?
O2 B1 C1 115.31(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 N1 1.9294(14) . ?
Cu1 N2 1.9482(14) . ?
Cu1 C1 1.9999(16) . ?
Cu1 C2 2.0819(16) . ?
Cl1 C15 1.740(2) . ?
Cl2 C19 1.730(2) . ?
Cl3 C21 1.7432(17) . ?
Cl4 C25 1.7368(18) . ?
O1 C4 1.439(2) . ?
O1 B1 1.361(2) . ?
O2 C6 1.439(2) . ?
O2 B1 1.370(2) . ?
N1 C10 1.331(2) . ?
N1 C14 1.413(2) . ?
N2 C12 1.330(2) . ?
N2 C20 1.415(2) . ?
C1 H1 1.0000 . ?
C1 C2 1.397(2) . ?
C1 B1 1.562(2) . ?
C2 C7 1.511(2) . ?
C2 C8 1.506(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.515(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.508(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9 C10 1.508(2) . ?
C10 C11 1.405(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.401(2) . ?
C12 C13 1.515(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.398(3) . ?
C14 C19 1.399(3) . ?
C15 C16 1.386(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.371(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(3) . ?
C20 C21 1.397(2) . ?
C20 C25 1.402(2) . ?
C21 C22 1.390(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.389(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.387(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8 H8A O1 0.98 2.37 3.072(2) 128.2 . yes
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 N1 C10 C9 -173.01(12) . . . . ?
Cu1 N1 C10 C11 6.9(2) . . . . ?
Cu1 N1 C14 C15 -92.53(18) . . . . ?
Cu1 N1 C14 C19 84.14(19) . . . . ?
Cu1 N2 C12 C11 2.1(2) . . . . ?
Cu1 N2 C12 C13 -177.10(12) . . . . ?
Cu1 N2 C20 C21 75.09(17) . . . . ?
Cu1 N2 C20 C25 -101.95(16) . . . . ?
Cu1 C1 C2 C7 98.64(15) . . . . ?
Cu1 C1 C2 C8 -103.83(16) . . . . ?
Cu1 C1 B1 O1 58.62(18) . . . . ?
Cu1 C1 B1 O2 -121.75(14) . . . . ?
Cl1 C15 C16 C17 -179.26(18) . . . . ?
Cl3 C21 C22 C23 179.20(13) . . . . ?
O1 C4 C5 C6 56.3(2) . . . . ?
N1 C10 C11 C12 -2.9(3) . . . . ?
N1 C14 C15 Cl1 -4.8(2) . . . . ?
N1 C14 C15 C16 175.98(19) . . . . ?
N1 C14 C19 Cl2 3.1(2) . . . . ?
N1 C14 C19 C18 -175.72(17) . . . . ?
N2 C20 C21 Cl3 0.9(2) . . . . ?
N2 C20 C21 C22 -179.12(15) . . . . ?
N2 C20 C25 Cl4 2.0(2) . . . . ?
N2 C20 C25 C24 -179.06(15) . . . . ?
C2 C1 B1 O1 -22.7(3) . . . . ?
C2 C1 B1 O2 156.88(16) . . . . ?
C4 O1 B1 O2 0.2(3) . . . . ?
C4 O1 B1 C1 179.79(15) . . . . ?
C4 C5 C6 O2 -54.4(2) . . . . ?
C6 O2 B1 O1 1.6(2) . . . . ?
C6 O2 B1 C1 -178.03(14) . . . . ?
C9 C10 C11 C12 176.94(17) . . . . ?
C10 N1 C14 C15 91.8(2) . . . . ?
C10 N1 C14 C19 -91.5(2) . . . . ?
C10 C11 C12 N2 -2.1(3) . . . . ?
C10 C11 C12 C13 177.12(16) . . . . ?
C12 N2 C20 C21 -105.23(18) . . . . ?
C12 N2 C20 C25 77.7(2) . . . . ?
C14 N1 C10 C9 2.5(2) . . . . ?
C14 N1 C10 C11 -177.67(15) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C14 C19 Cl2 179.94(14) . . . . ?
C15 C14 C19 C18 1.1(3) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C17 C18 C19 Cl2 -179.30(17) . . . . ?
C17 C18 C19 C14 -0.5(3) . . . . ?
C19 C14 C15 Cl1 178.38(14) . . . . ?
C19 C14 C15 C16 -0.9(3) . . . . ?
C20 N2 C12 C11 -177.56(15) . . . . ?
C20 N2 C12 C13 3.2(2) . . . . ?
C20 C21 C22 C23 -0.8(3) . . . . ?
C21 C20 C25 Cl4 -175.19(12) . . . . ?
C21 C20 C25 C24 3.7(2) . . . . ?
C21 C22 C23 C24 1.8(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 Cl4 176.10(13) . . . . ?
C23 C24 C25 C20 -2.8(3) . . . . ?
C25 C20 C21 Cl3 178.12(12) . . . . ?
C25 C20 C21 C22 -1.9(2) . . . . ?
B1 O1 C4 C5 -29.8(2) . . . . ?
B1 O2 C6 C5 26.6(2) . . . . ?
B1 C1 C2 Cu1 98.44(17) . . . . ?
B1 C1 C2 C7 -162.92(16) . . . . ?
B1 C1 C2 C8 -5.4(3) . . . . ?
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
-1.6360 6.8360 -6.4966 0.2648 -0.4853 0.8333
-1.0597 -6.9102 -7.0403 -0.4488 0.8279 0.3364
1.6632 -6.7351 6.6584 -0.2575 0.4718 -0.8433
1.1028 6.7897 7.2265 0.4451 -0.8211 -0.3573
-0.9992 0.0007 0.0004 -0.1273 -0.0466 0.0871
0.9992 -0.0007 -0.0004 0.1273 0.0466 -0.0871
