#------------------------------------------------------------------------------
#$Date: 2020-04-23 22:50:22 +0300 (Thu, 23 Apr 2020) $
#$Revision: 251089 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/47/4134783.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_4134783
loop_
_publ_author_name
'Bower, Jamey K.'
'Cypcar, Andrew D.'
'Henriquez, Brenda'
'Stieber, S Chantal E'
'Zhang, Shiyu'
_publ_section_title
;
 C(sp³)-H Fluorination with a Copper(II)/(III) Redox Couple.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c02583
_journal_year                    2020
_chemical_formula_moiety         'C31 H37 Br Cu N3 O2, 2(C4 H8 O), C16 H36 N'
_chemical_formula_sum            'C55 H89 Br Cu N4 O4'
_chemical_formula_weight         1013.75
_chemical_name_systematic
;        
Tetrabutylammonium [N,N'-Bis(2,6-diisopropylphenyl)-
2,6-pyridinedicarboxamido] copper bromide
;
_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
_audit_creation_date             2020-01-25
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.079(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2228(4)
_cell_length_b                   26.7001(10)
_cell_length_c                   20.4820(8)
_cell_measurement_reflns_used    9291
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.436
_cell_measurement_theta_min      2.503
_cell_volume                     5486.4(4)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_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)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            115502
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.530
_diffrn_reflns_theta_min         1.268
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.172
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0602 before and 0.0499 after correction. 
The Ratio of minimum to maximum transmission is 0.8326. 
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       block
_exptl_crystal_F_000             2172
_exptl_crystal_recrystallization_method
;
Grown from a concentrated tetrahydrofuran solution 
layered with diethyl ether at -35C.
;
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     598
_refine_ls_number_reflns         11372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0366
_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)+(0.0526P)²+3.4677P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9340
_reflns_number_total             11372
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c02583_si_004.cif
_cod_data_source_block           pdacubrtba
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4134783
_shelx_shelxl_version_number     2018/1
_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.
;
_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:
 C13(H13), C16(H16), C26(H26), C29(H29)
2.b Secondary CH2 refined with riding coordinates:
 C1C(H1CA,H1CB), C2C(H2CA,H2CB), C3C(H3CA,H3CB), C4C(H4CA,H4CB), C1B(H1BA,
 H1BB), C2B(H2BA,H2BB), C3B(H3BA,H3BB), C4B(H4BA,H4BB), C1A(H1AA,H1AB),
 C2A(H2AA,H2AB), C3A(H3AA,H3AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C7A(H7AA,H7AB),
  C9A(H9AA,H9AB), C10A(H10A,H10B), C11A(H11A,H11B), C13A(H13A,H13B), C14A(H14D,
 H14E), C15A(H15D,H15E)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C22(H22), C23(H23),
 C24(H24)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C31(H31A,
 H31B,H31C), C4A(H4AA,H4AB,H4AC), C8A(H8AA,H8AB,H8AC), C12A(H12A,H12B,H12C),
 C16A(H16A,H16B,H16C)
;
_olex2_exptl_crystal_mounting_method
'Mounted on a MiTeGen mount with Paratone oil'
_olex2_submission_original_sample_id '[TBA]PDACuBr'
_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
Br1 Br 0.53163(2) 0.41284(2) 0.26426(2) 0.02528(7) Uani 1 1 d . . . . .
Cu1 Cu 0.32473(2) 0.38710(2) 0.28615(2) 0.01480(7) Uani 1 1 d . . . . .
O1 O 0.25763(15) 0.24393(5) 0.33967(8) 0.0272(3) Uani 1 1 d . . . . .
O2 O 0.00536(14) 0.48044(5) 0.24133(8) 0.0263(3) Uani 1 1 d . . . . .
N1 N 0.14699(16) 0.36457(6) 0.29244(8) 0.0173(3) Uani 1 1 d . . . . .
N2 N 0.36564(16) 0.31692(6) 0.31869(8) 0.0164(3) Uani 1 1 d . . . . .
N3 N 0.22116(16) 0.45018(6) 0.26316(8) 0.0159(3) Uani 1 1 d . . . . .
C1 C 0.0459(2) 0.39641(8) 0.27770(10) 0.0183(4) Uani 1 1 d . . . . .
C2 C -0.0812(2) 0.38194(8) 0.28188(11) 0.0223(4) Uani 1 1 d . . . . .
H2 H -0.153903 0.404528 0.270932 0.027 Uiso 1 1 calc R . . . .
C3 C -0.1006(2) 0.33328(8) 0.30259(12) 0.0264(5) Uani 1 1 d . . . . .
H3 H -0.187358 0.322335 0.306156 0.032 Uiso 1 1 calc R . . . .
C4 C 0.0070(2) 0.30074(8) 0.31805(11) 0.0246(5) Uani 1 1 d . . . . .
H4 H -0.004953 0.267497 0.332368 0.030 Uiso 1 1 calc R . . . .
C5 C 0.1319(2) 0.31779(7) 0.31212(10) 0.0188(4) Uani 1 1 d . . . . .
C6 C 0.2602(2) 0.28894(7) 0.32507(10) 0.0199(4) Uani 1 1 d . . . . .
C7 C 0.48948(19) 0.29039(7) 0.32855(10) 0.0163(4) Uani 1 1 d . . . . .
C8 C 0.5259(2) 0.26428(7) 0.27533(10) 0.0200(4) Uani 1 1 d . . . . .
C9 C 0.6409(2) 0.23531(8) 0.28743(11) 0.0235(5) Uani 1 1 d . . . . .
H9 H 0.665664 0.217068 0.251873 0.028 Uiso 1 1 calc R . . . .
C10 C 0.7198(2) 0.23249(8) 0.34999(11) 0.0249(5) Uani 1 1 d . . . . .
H10 H 0.796503 0.211610 0.357692 0.030 Uiso 1 1 calc R . . . .
C11 C 0.6868(2) 0.26012(8) 0.40120(11) 0.0246(5) Uani 1 1 d . . . . .
H11 H 0.743441 0.259066 0.443774 0.029 Uiso 1 1 calc R . . . .
C12 C 0.5722(2) 0.28960(8) 0.39208(10) 0.0206(4) Uani 1 1 d . . . . .
C13 C 0.4440(2) 0.26705(9) 0.20554(11) 0.0283(5) Uani 1 1 d . . . . .
H13 H 0.365419 0.289088 0.206781 0.034 Uiso 1 1 calc R . . . .
C14 C 0.5231(3) 0.29029(10) 0.15762(12) 0.0412(6) Uani 1 1 d . . . . .
H14A H 0.556508 0.323185 0.174346 0.062 Uiso 1 1 calc GR . . . .
H14B H 0.465415 0.294167 0.113810 0.062 Uiso 1 1 calc GR . . . .
H14C H 0.598431 0.268511 0.153799 0.062 Uiso 1 1 calc GR . . . .
C15 C 0.3915(3) 0.21539(10) 0.18096(13) 0.0421(7) Uani 1 1 d . . . . .
H15A H 0.466717 0.193086 0.178916 0.063 Uiso 1 1 calc GR . . . .
H15B H 0.335727 0.218522 0.136538 0.063 Uiso 1 1 calc GR . . . .
H15C H 0.338355 0.201475 0.211686 0.063 Uiso 1 1 calc GR . . . .
C16 C 0.5380(2) 0.32032(9) 0.44853(11) 0.0307(5) Uani 1 1 d . . . . .
H16 H 0.438607 0.322329 0.441288 0.037 Uiso 1 1 calc R . . . .
C17 C 0.5890(4) 0.37305(10) 0.44714(14) 0.0595(9) Uani 1 1 d . . . . .
H17A H 0.686628 0.372672 0.454752 0.089 Uiso 1 1 calc GR . . . .
H17B H 0.559804 0.392749 0.482098 0.089 Uiso 1 1 calc GR . . . .
H17C H 0.553844 0.388113 0.403681 0.089 Uiso 1 1 calc GR . . . .
C18 C 0.5855(3) 0.29792(10) 0.51708(12) 0.0405(6) Uani 1 1 d . . . . .
H18A H 0.555536 0.263058 0.517250 0.061 Uiso 1 1 calc GR . . . .
H18B H 0.548439 0.317162 0.550014 0.061 Uiso 1 1 calc GR . . . .
H18C H 0.683024 0.299072 0.528235 0.061 Uiso 1 1 calc GR . . . .
C19 C 0.0893(2) 0.44734(7) 0.25833(10) 0.0183(4) Uani 1 1 d . . . . .
C20 C 0.26767(19) 0.49806(7) 0.24647(10) 0.0164(4) Uani 1 1 d . . . . .
C21 C 0.2747(2) 0.50823(8) 0.18034(10) 0.0197(4) Uani 1 1 d . . . . .
C22 C 0.3180(2) 0.55558(8) 0.16513(11) 0.0245(5) Uani 1 1 d . . . . .
H22 H 0.323445 0.563257 0.120446 0.029 Uiso 1 1 calc R . . . .
C23 C 0.3531(2) 0.59148(8) 0.21378(12) 0.0263(5) Uani 1 1 d . . . . .
H23 H 0.382440 0.623544 0.202566 0.032 Uiso 1 1 calc R . . . .
C24 C 0.3453(2) 0.58064(8) 0.27881(12) 0.0257(5) Uani 1 1 d . . . . .
H24 H 0.370527 0.605392 0.312172 0.031 Uiso 1 1 calc R . . . .
C25 C 0.3013(2) 0.53408(8) 0.29647(11) 0.0216(4) Uani 1 1 d . . . . .
C26 C 0.2296(2) 0.47000(9) 0.12590(11) 0.0260(5) Uani 1 1 d . . . . .
H26 H 0.204079 0.438931 0.147694 0.031 Uiso 1 1 calc R . . . .
C27 C 0.1051(2) 0.48868(11) 0.07833(13) 0.0393(6) Uani 1 1 d . . . . .
H27A H 0.034470 0.495517 0.103403 0.059 Uiso 1 1 calc GR . . . .
H27B H 0.074651 0.463026 0.044618 0.059 Uiso 1 1 calc GR . . . .
H27C H 0.126384 0.519473 0.056516 0.059 Uiso 1 1 calc GR . . . .
C28 C 0.3385(2) 0.45584(9) 0.08846(12) 0.0326(5) Uani 1 1 d . . . . .
H28A H 0.367947 0.485780 0.067655 0.049 Uiso 1 1 calc GR . . . .
H28B H 0.303933 0.431184 0.054008 0.049 Uiso 1 1 calc GR . . . .
H28C H 0.414028 0.441414 0.119513 0.049 Uiso 1 1 calc GR . . . .
C29 C 0.2841(3) 0.52330(9) 0.36715(11) 0.0311(5) Uani 1 1 d . . . . .
H29 H 0.236640 0.490448 0.365722 0.037 Uiso 1 1 calc R . . . .
C30 C 0.1954(3) 0.56162(15) 0.39235(14) 0.0596(9) Uani 1 1 d . . . . .
H30A H 0.240473 0.594163 0.397456 0.089 Uiso 1 1 calc GR . . . .
H30B H 0.177342 0.550715 0.435454 0.089 Uiso 1 1 calc GR . . . .
H30C H 0.111100 0.564643 0.360381 0.089 Uiso 1 1 calc GR . . . .
C31 C 0.4119(3) 0.51712(14) 0.41485(14) 0.0551(8) Uani 1 1 d . . . . .
H31A H 0.462466 0.489439 0.400339 0.083 Uiso 1 1 calc GR . . . .
H31B H 0.393896 0.509749 0.459153 0.083 Uiso 1 1 calc GR . . . .
H31C H 0.463957 0.548088 0.416583 0.083 Uiso 1 1 calc GR . . . .
O1C O 0.1366(3) 0.34957(12) 0.55321(16) 0.0962(10) Uani 1 1 d . . . . .
C1C C 0.0306(5) 0.3715(2) 0.5122(4) 0.128(2) Uani 1 1 d . . . . .
H1CA H -0.025099 0.389351 0.539291 0.154 Uiso 1 1 calc R . . . .
H1CB H -0.024930 0.345400 0.486000 0.154 Uiso 1 1 calc R . . . .
C2C C 0.0764(5) 0.40654(19) 0.4676(2) 0.0926(16) Uani 1 1 d . . . . .
H2CA H 0.060449 0.441502 0.480121 0.111 Uiso 1 1 calc R . . . .
H2CB H 0.030313 0.400810 0.421081 0.111 Uiso 1 1 calc R . . . .
C3C C 0.2240(4) 0.39623(13) 0.47543(15) 0.0557(8) Uani 1 1 d . . . . .
H3CA H 0.249036 0.389469 0.431913 0.067 Uiso 1 1 calc R . . . .
H3CB H 0.277574 0.424653 0.497159 0.067 Uiso 1 1 calc R . . . .
C4C C 0.2418(4) 0.35108(15) 0.5184(2) 0.0745(11) Uani 1 1 d . . . . .
H4CA H 0.241057 0.320574 0.490829 0.089 Uiso 1 1 calc R . . . .
H4CB H 0.328149 0.352699 0.549952 0.089 Uiso 1 1 calc R . . . .
O1B O -0.0023(2) 0.31605(10) -0.05878(13) 0.0676(7) Uani 1 1 d . . . . .
C1B C 0.0669(3) 0.27676(13) -0.0199(2) 0.0689(10) Uani 1 1 d . . . . .
H1BA H 0.146229 0.266537 -0.037715 0.083 Uiso 1 1 calc R . . . .
H1BB H 0.008176 0.247275 -0.019848 0.083 Uiso 1 1 calc R . . . .
C2B C 0.1084(4) 0.29779(19) 0.0504(2) 0.0877(14) Uani 1 1 d . . . . .
H2BA H 0.192370 0.317107 0.055473 0.105 Uiso 1 1 calc R . . . .
H2BB H 0.118401 0.270963 0.084362 0.105 Uiso 1 1 calc R . . . .
C3B C -0.0105(5) 0.3316(2) 0.0542(2) 0.0981(16) Uani 1 1 d . . . . .
H3BA H -0.084701 0.312429 0.066727 0.118 Uiso 1 1 calc R . . . .
H3BB H 0.015061 0.359202 0.086431 0.118 Uiso 1 1 calc R . . . .
C4B C -0.0469(4) 0.35097(15) -0.0148(2) 0.0749(11) Uani 1 1 d . . . . .
H4BA H -0.144795 0.355186 -0.027225 0.090 Uiso 1 1 calc R . . . .
H4BB H -0.004616 0.383991 -0.018062 0.090 Uiso 1 1 calc R . . . .
N1A N 0.76441(16) 0.58844(6) 0.18639(8) 0.0170(4) Uani 1 1 d . . . . .
C1A C 0.6684(2) 0.62573(7) 0.14659(10) 0.0187(4) Uani 1 1 d . . . . .
H1AA H 0.577889 0.611022 0.139017 0.022 Uiso 1 1 calc R . . . .
H1AB H 0.666891 0.656154 0.174063 0.022 Uiso 1 1 calc R . . . .
C2A C 0.6979(2) 0.64150(9) 0.08006(11) 0.0272(5) Uani 1 1 d . . . . .
H2AA H 0.705431 0.611459 0.052702 0.033 Uiso 1 1 calc R . . . .
H2AB H 0.783983 0.659597 0.086844 0.033 Uiso 1 1 calc R . . . .
C3A C 0.5875(2) 0.67529(8) 0.04384(11) 0.0252(5) Uani 1 1 d . . . . .
H3AA H 0.571538 0.702287 0.074507 0.030 Uiso 1 1 calc R . . . .
H3AB H 0.618311 0.691216 0.005848 0.030 Uiso 1 1 calc R . . . .
C4A C 0.4583(3) 0.64918(9) 0.01835(14) 0.0415(7) Uani 1 1 d . . . . .
H4AA H 0.473120 0.621687 -0.011086 0.062 Uiso 1 1 calc GR . . . .
H4AB H 0.394512 0.672999 -0.006454 0.062 Uiso 1 1 calc GR . . . .
H4AC H 0.422628 0.635749 0.055885 0.062 Uiso 1 1 calc GR . . . .
C5A C 0.7820(2) 0.54265(8) 0.14523(11) 0.0205(4) Uani 1 1 d . . . . .
H5AA H 0.828545 0.552961 0.109231 0.025 Uiso 1 1 calc R . . . .
H5AB H 0.840658 0.518634 0.173923 0.025 Uiso 1 1 calc R . . . .
C6A C 0.6549(2) 0.51577(8) 0.11417(12) 0.0260(5) Uani 1 1 d . . . . .
H6AA H 0.595518 0.538980 0.084475 0.031 Uiso 1 1 calc R . . . .
H6AB H 0.607671 0.504500 0.149475 0.031 Uiso 1 1 calc R . . . .
C7A C 0.6876(2) 0.47050(8) 0.07426(11) 0.0270(5) Uani 1 1 d . . . . .
H7AA H 0.604721 0.458842 0.044912 0.032 Uiso 1 1 calc R . . . .
H7AB H 0.750088 0.481142 0.045517 0.032 Uiso 1 1 calc R . . . .
C8A C 0.7491(3) 0.42703(8) 0.11738(13) 0.0320(5) Uani 1 1 d . . . . .
H8AA H 0.763071 0.398795 0.088925 0.048 Uiso 1 1 calc GR . . . .
H8AB H 0.688986 0.416803 0.146911 0.048 Uiso 1 1 calc GR . . . .
H8AC H 0.834768 0.437446 0.144101 0.048 Uiso 1 1 calc GR . . . .
C9A C 0.7042(2) 0.57417(8) 0.24593(10) 0.0189(4) Uani 1 1 d . . . . .
H9AA H 0.692225 0.605099 0.270789 0.023 Uiso 1 1 calc R . . . .
H9AB H 0.614536 0.559927 0.229384 0.023 Uiso 1 1 calc R . . . .
C10A C 0.7829(2) 0.53714(8) 0.29400(11) 0.0246(5) Uani 1 1 d . . . . .
H10A H 0.789548 0.504810 0.271195 0.029 Uiso 1 1 calc R . . . .
H10B H 0.874232 0.550006 0.310049 0.029 Uiso 1 1 calc R . . . .
C11A C 0.7138(2) 0.52947(9) 0.35222(11) 0.0294(5) Uani 1 1 d . . . . .
H11A H 0.620672 0.518761 0.335444 0.035 Uiso 1 1 calc R . . . .
H11B H 0.711293 0.561667 0.375925 0.035 Uiso 1 1 calc R . . . .
C12A C 0.7837(3) 0.49047(10) 0.40057(12) 0.0378(6) Uani 1 1 d . . . . .
H12A H 0.781183 0.457999 0.378047 0.057 Uiso 1 1 calc GR . . . .
H12B H 0.738446 0.487728 0.438483 0.057 Uiso 1 1 calc GR . . . .
H12C H 0.876603 0.500489 0.416395 0.057 Uiso 1 1 calc GR . . . .
C13A C 0.9029(2) 0.61068(8) 0.20808(11) 0.0205(4) Uani 1 1 d . . . . .
H13A H 0.964501 0.583552 0.227284 0.025 Uiso 1 1 calc R . . . .
H13B H 0.933521 0.623294 0.168102 0.025 Uiso 1 1 calc R . . . .
C14A C 0.9138(2) 0.65276(8) 0.25825(11) 0.0235(5) Uani 1 1 d . . . . .
H14D H 0.889992 0.640167 0.299901 0.028 Uiso 1 1 calc R . . . .
H14E H 0.850493 0.679767 0.240562 0.028 Uiso 1 1 calc R . . . .
C15A C 1.0551(2) 0.67360(9) 0.27294(12) 0.0314(5) Uani 1 1 d . . . . .
H15D H 1.118562 0.646046 0.287951 0.038 Uiso 1 1 calc R . . . .
H15E H 1.076761 0.687745 0.231620 0.038 Uiso 1 1 calc R . . . .
C16A C 1.0714(3) 0.71397(11) 0.32606(14) 0.0446(7) Uani 1 1 d . . . . .
H16A H 1.009282 0.741456 0.311175 0.067 Uiso 1 1 calc GR . . . .
H16B H 1.163028 0.726693 0.333887 0.067 Uiso 1 1 calc GR . . . .
H16C H 1.052480 0.699843 0.367418 0.067 Uiso 1 1 calc GR . . . .
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'
Br Br -0.2901 2.4595 '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
N1 Cu1 Br1 172.89(5) . . ?
N1 Cu1 N2 80.01(7) . . ?
N1 Cu1 N3 79.42(7) . . ?
N2 Cu1 Br1 101.47(5) . . ?
N3 Cu1 Br1 99.47(5) . . ?
N3 Cu1 N2 158.99(7) . . ?
C1 N1 Cu1 118.95(14) . . ?
C1 N1 C5 122.67(18) . . ?
C5 N1 Cu1 118.38(14) . . ?
C6 N2 Cu1 115.68(13) . . ?
C6 N2 C7 114.68(16) . . ?
C7 N2 Cu1 129.18(13) . . ?
C19 N3 Cu1 116.85(13) . . ?
C19 N3 C20 114.27(16) . . ?
C20 N3 Cu1 128.73(12) . . ?
N1 C1 C2 120.66(19) . . ?
N1 C1 C19 112.44(17) . . ?
C2 C1 C19 126.89(18) . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.24(19) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.56(19) . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 119.89(19) . . ?
N1 C5 C6 112.81(17) . . ?
C4 C5 C6 127.30(18) . . ?
O1 C6 N2 128.23(19) . . ?
O1 C6 C5 118.85(18) . . ?
N2 C6 C5 112.92(17) . . ?
C8 C7 N2 119.74(17) . . ?
C8 C7 C12 120.53(18) . . ?
C12 C7 N2 119.70(18) . . ?
C7 C8 C13 121.88(18) . . ?
C9 C8 C7 118.68(19) . . ?
C9 C8 C13 119.43(19) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.3(2) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.6(2) . . ?
C12 C11 H11 119.2 . . ?
C7 C12 C16 120.80(19) . . ?
C11 C12 C7 118.17(19) . . ?
C11 C12 C16 121.03(19) . . ?
C8 C13 H13 107.8 . . ?
C8 C13 C14 111.3(2) . . ?
C8 C13 C15 111.24(19) . . ?
C14 C13 H13 107.8 . . ?
C14 C13 C15 110.6(2) . . ?
C15 C13 H13 107.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16 107.1 . . ?
C12 C16 C18 114.4(2) . . ?
C17 C16 C12 111.2(2) . . ?
C17 C16 H16 107.1 . . ?
C17 C16 C18 109.7(2) . . ?
C18 C16 H16 107.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2 C19 N3 128.15(19) . . ?
O2 C19 C1 119.74(18) . . ?
N3 C19 C1 112.11(17) . . ?
C21 C20 N3 119.18(18) . . ?
C21 C20 C25 121.68(19) . . ?
C25 C20 N3 119.11(18) . . ?
C20 C21 C26 121.14(18) . . ?
C22 C21 C20 118.07(19) . . ?
C22 C21 C26 120.71(19) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.2(2) . . ?
C23 C22 H22 119.4 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.8(2) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.4 . . ?
C23 C24 C25 121.3(2) . . ?
C25 C24 H24 119.4 . . ?
C20 C25 C29 120.69(19) . . ?
C24 C25 C20 118.0(2) . . ?
C24 C25 C29 121.2(2) . . ?
C21 C26 H26 107.4 . . ?
C21 C26 C27 110.31(19) . . ?
C27 C26 H26 107.4 . . ?
C28 C26 C21 112.97(19) . . ?
C28 C26 H26 107.4 . . ?
C28 C26 C27 111.17(19) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C29 H29 106.4 . . ?
C25 C29 C30 112.4(2) . . ?
C30 C29 H29 106.4 . . ?
C31 C29 C25 113.6(2) . . ?
C31 C29 H29 106.4 . . ?
C31 C29 C30 111.0(2) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C1C O1C C4C 105.7(3) . . ?
O1C C1C H1CA 109.5 . . ?
O1C C1C H1CB 109.5 . . ?
O1C C1C C2C 110.5(4) . . ?
H1CA C1C H1CB 108.1 . . ?
C2C C1C H1CA 109.5 . . ?
C2C C1C H1CB 109.5 . . ?
C1C C2C H2CA 110.8 . . ?
C1C C2C H2CB 110.8 . . ?
C1C C2C C3C 104.6(3) . . ?
H2CA C2C H2CB 108.9 . . ?
C3C C2C H2CA 110.8 . . ?
C3C C2C H2CB 110.8 . . ?
C2C C3C H3CA 111.3 . . ?
C2C C3C H3CB 111.3 . . ?
H3CA C3C H3CB 109.2 . . ?
C4C C3C C2C 102.6(3) . . ?
C4C C3C H3CA 111.3 . . ?
C4C C3C H3CB 111.3 . . ?
O1C C4C C3C 107.9(3) . . ?
O1C C4C H4CA 110.1 . . ?
O1C C4C H4CB 110.1 . . ?
C3C C4C H4CA 110.1 . . ?
C3C C4C H4CB 110.1 . . ?
H4CA C4C H4CB 108.4 . . ?
C1B O1B C4B 108.2(3) . . ?
O1B C1B H1BA 110.5 . . ?
O1B C1B H1BB 110.5 . . ?
O1B C1B C2B 106.0(3) . . ?
H1BA C1B H1BB 108.7 . . ?
C2B C1B H1BA 110.5 . . ?
C2B C1B H1BB 110.5 . . ?
C1B C2B H2BA 111.6 . . ?
C1B C2B H2BB 111.6 . . ?
C1B C2B C3B 100.7(3) . . ?
H2BA C2B H2BB 109.4 . . ?
C3B C2B H2BA 111.6 . . ?
C3B C2B H2BB 111.6 . . ?
C2B C3B H3BA 111.3 . . ?
C2B C3B H3BB 111.3 . . ?
H3BA C3B H3BB 109.2 . . ?
C4B C3B C2B 102.4(3) . . ?
C4B C3B H3BA 111.3 . . ?
C4B C3B H3BB 111.3 . . ?
O1B C4B C3B 108.7(3) . . ?
O1B C4B H4BA 109.9 . . ?
O1B C4B H4BB 109.9 . . ?
C3B C4B H4BA 109.9 . . ?
C3B C4B H4BB 109.9 . . ?
H4BA C4B H4BB 108.3 . . ?
C1A N1A C13A 111.69(15) . . ?
C5A N1A C1A 111.32(15) . . ?
C5A N1A C9A 110.78(15) . . ?
C5A N1A C13A 105.89(15) . . ?
C9A N1A C1A 106.02(15) . . ?
C9A N1A C13A 111.24(15) . . ?
N1A C1A H1AA 108.2 . . ?
N1A C1A H1AB 108.2 . . ?
H1AA C1A H1AB 107.3 . . ?
C2A C1A N1A 116.50(16) . . ?
C2A C1A H1AA 108.2 . . ?
C2A C1A H1AB 108.2 . . ?
C1A C2A H2AA 109.6 . . ?
C1A C2A H2AB 109.6 . . ?
C1A C2A C3A 110.31(18) . . ?
H2AA C2A H2AB 108.1 . . ?
C3A C2A H2AA 109.6 . . ?
C3A C2A H2AB 109.6 . . ?
C2A C3A H3AA 108.6 . . ?
C2A C3A H3AB 108.6 . . ?
H3AA C3A H3AB 107.6 . . ?
C4A C3A C2A 114.61(19) . . ?
C4A C3A H3AA 108.6 . . ?
C4A C3A H3AB 108.6 . . ?
C3A C4A H4AA 109.5 . . ?
C3A C4A H4AB 109.5 . . ?
C3A C4A H4AC 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
N1A C5A H5AA 108.4 . . ?
N1A C5A H5AB 108.4 . . ?
H5AA C5A H5AB 107.4 . . ?
C6A C5A N1A 115.58(17) . . ?
C6A C5A H5AA 108.4 . . ?
C6A C5A H5AB 108.4 . . ?
C5A C6A H6AA 109.7 . . ?
C5A C6A H6AB 109.7 . . ?
C5A C6A C7A 109.89(18) . . ?
H6AA C6A H6AB 108.2 . . ?
C7A C6A H6AA 109.7 . . ?
C7A C6A H6AB 109.7 . . ?
C6A C7A H7AA 108.8 . . ?
C6A C7A H7AB 108.8 . . ?
H7AA C7A H7AB 107.7 . . ?
C8A C7A C6A 113.64(19) . . ?
C8A C7A H7AA 108.8 . . ?
C8A C7A H7AB 108.8 . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
N1A C9A H9AA 108.3 . . ?
N1A C9A H9AB 108.3 . . ?
H9AA C9A H9AB 107.4 . . ?
C10A C9A N1A 116.11(16) . . ?
C10A C9A H9AA 108.3 . . ?
C10A C9A H9AB 108.3 . . ?
C9A C10A H10A 109.8 . . ?
C9A C10A H10B 109.8 . . ?
H10A C10A H10B 108.3 . . ?
C11A C10A C9A 109.33(18) . . ?
C11A C10A H10A 109.8 . . ?
C11A C10A H10B 109.8 . . ?
C10A C11A H11A 109.2 . . ?
C10A C11A H11B 109.2 . . ?
C10A C11A C12A 112.0(2) . . ?
H11A C11A H11B 107.9 . . ?
C12A C11A H11A 109.2 . . ?
C12A C11A H11B 109.2 . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
N1A C13A H13A 108.4 . . ?
N1A C13A H13B 108.4 . . ?
H13A C13A H13B 107.5 . . ?
C14A C13A N1A 115.55(17) . . ?
C14A C13A H13A 108.4 . . ?
C14A C13A H13B 108.4 . . ?
C13A C14A H14D 109.6 . . ?
C13A C14A H14E 109.6 . . ?
C13A C14A C15A 110.42(18) . . ?
H14D C14A H14E 108.1 . . ?
C15A C14A H14D 109.6 . . ?
C15A C14A H14E 109.6 . . ?
C14A C15A H15D 109.3 . . ?
C14A C15A H15E 109.3 . . ?
H15D C15A H15E 107.9 . . ?
C16A C15A C14A 111.8(2) . . ?
C16A C15A H15D 109.3 . . ?
C16A C15A H15E 109.3 . . ?
C15A C16A H16A 109.5 . . ?
C15A C16A H16B 109.5 . . ?
C15A C16A H16C 109.5 . . ?
H16A C16A H16B 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
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
Br1 Cu1 2.3475(3) . ?
Cu1 N1 1.9417(17) . ?
Cu1 N2 2.0059(16) . ?
Cu1 N3 1.9969(16) . ?
O1 C6 1.240(2) . ?
O2 C19 1.235(2) . ?
N1 C1 1.328(3) . ?
N1 C5 1.330(3) . ?
N2 C6 1.339(3) . ?
N2 C7 1.431(2) . ?
N3 C19 1.334(3) . ?
N3 C20 1.428(2) . ?
C1 C2 1.373(3) . ?
C1 C19 1.507(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(3) . ?
C5 C6 1.499(3) . ?
C7 C8 1.403(3) . ?
C7 C12 1.409(3) . ?
C8 C9 1.389(3) . ?
C8 C13 1.513(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.379(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(3) . ?
C12 C16 1.512(3) . ?
C13 H13 1.0000 . ?
C13 C14 1.519(4) . ?
C13 C15 1.530(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 1.0000 . ?
C16 C17 1.503(4) . ?
C16 C18 1.517(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 C21 1.397(3) . ?
C20 C25 1.399(3) . ?
C21 C22 1.394(3) . ?
C21 C26 1.517(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.379(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.380(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.393(3) . ?
C25 C29 1.519(3) . ?
C26 H26 1.0000 . ?
C26 C27 1.530(3) . ?
C26 C28 1.516(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29 1.0000 . ?
C29 C30 1.522(4) . ?
C29 C31 1.483(4) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
O1C C1C 1.368(6) . ?
O1C C4C 1.401(4) . ?
C1C H1CA 0.9900 . ?
C1C H1CB 0.9900 . ?
C1C C2C 1.447(7) . ?
C2C H2CA 0.9900 . ?
C2C H2CB 0.9900 . ?
C2C C3C 1.511(5) . ?
C3C H3CA 0.9900 . ?
C3C H3CB 0.9900 . ?
C3C C4C 1.483(5) . ?
C4C H4CA 0.9900 . ?
C4C H4CB 0.9900 . ?
O1B C1B 1.421(4) . ?
O1B C4B 1.431(4) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C1B C2B 1.527(6) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C2B C3B 1.528(5) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C3B C4B 1.483(6) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
N1A C1A 1.520(2) . ?
N1A C5A 1.515(3) . ?
N1A C9A 1.517(3) . ?
N1A C13A 1.521(3) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C1A C2A 1.511(3) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.522(3) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A C4A 1.496(3) . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A H4AC 0.9800 . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5A C6A 1.514(3) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C6A C7A 1.532(3) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C7A C8A 1.519(3) . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C10A 1.513(3) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C10A C11A 1.512(3) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C11A C12A 1.518(3) . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C13A C14A 1.512(3) . ?
C14A H14D 0.9900 . ?
C14A H14E 0.9900 . ?
C14A C15A 1.523(3) . ?
C15A H15D 0.9900 . ?
C15A H15E 0.9900 . ?
C15A C16A 1.518(4) . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
