# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1559217'
# Added during the CSD deposition process: Wednesday 28 June 2017 06:48 PM
# end Validation Reply Form


_audit_update_record             
;
2017-06-28 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_3                   
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          16 Note
RESPONSE: This is due to a large beamstop shadowing (technicians in charge striving for detector preservation???)
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H25 Br Cu N2 P'
_chemical_formula_sum            'C30 H25 Br Cu N2 P'
_chemical_formula_weight         587.94

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'
P P 0.1023 0.0942 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8211(3)
_cell_length_b                   10.3594(3)
_cell_length_c                   16.2494(4)
_cell_angle_alpha                77.816(2)
_cell_angle_beta                 84.816(2)
_cell_angle_gamma                65.413(3)
_cell_volume                     1319.84(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4550
_cell_measurement_theta_min      3.882
_cell_measurement_theta_max      26.548

_exptl_crystal_description       fragment
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   0.60
_exptl_transmission_factor_max   0.71
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    2.423
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro (Oxford Diffraction, 2009)'
_diffrn_ambient_temperature      294(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_measurement_method       'ω scans'

_diffrn_reflns_number            19767
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.849
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5160
_reflns_number_gt                3527
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5160
_refine_ls_number_parameters     316
_refine_ls_number_restraints     294
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.21553(4) 0.48807(3) 0.32430(2) 0.04776(11) Uani 1 1 d . U . . .
Br1 Br 0.08397(4) 0.32098(3) 0.32941(2) 0.06436(12) Uani 1 1 d . U . . .
P1 P 0.08235(8) 0.71008(7) 0.25502(4) 0.03972(16) Uani 1 1 d . U . . .
N1 N 0.3126(3) 0.4344(2) 0.44771(12) 0.0451(5) Uani 1 1 d . U . . .
N2 N 0.4732(2) 0.3750(2) 0.30199(13) 0.0438(5) Uani 1 1 d . U . . .
C11 C -0.0185(3) 0.7334(3) 0.15610(14) 0.0398(5) Uani 1 1 d . U . . .
C21 C -0.0673(3) 0.8621(3) 0.09712(16) 0.0535(7) Uani 1 1 d . U . . .
H21 H -0.0499 0.9396 0.1078 0.064 Uiso 1 1 calc R U . . .
C31 C -0.1415(3) 0.8748(3) 0.02283(16) 0.0608(7) Uani 1 1 d . U . . .
H31 H -0.1753 0.9615 -0.0159 0.073 Uiso 1 1 calc R U . . .
C41 C -0.1655(3) 0.7621(3) 0.00588(17) 0.0571(7) Uani 1 1 d . U . . .
H41 H -0.2139 0.7710 -0.0447 0.069 Uiso 1 1 calc R U . . .
C51 C -0.1187(3) 0.6356(3) 0.06305(16) 0.0568(7) Uani 1 1 d . U . . .
H51 H -0.1368 0.5588 0.0516 0.068 Uiso 1 1 calc R U . . .
C61 C -0.0442(3) 0.6205(3) 0.13839(16) 0.0489(6) Uani 1 1 d . U . . .
H61 H -0.0116 0.5335 0.1769 0.059 Uiso 1 1 calc R U . . .
C12 C 0.2101(3) 0.8129(3) 0.22088(14) 0.0407(5) Uani 1 1 d . U . . .
C22 C 0.1740(3) 0.9481(3) 0.23780(17) 0.0526(6) Uani 1 1 d . U . . .
H22 H 0.0794 0.9920 0.2690 0.063 Uiso 1 1 calc R U . . .
C32 C 0.2773(4) 1.0186(3) 0.20868(19) 0.0635(7) Uani 1 1 d . U . . .
H32 H 0.2515 1.1096 0.2202 0.076 Uiso 1 1 calc R U . . .
C42 C 0.4162(4) 0.9552(3) 0.16325(19) 0.0637(7) Uani 1 1 d . U . . .
H42 H 0.4849 1.0031 0.1435 0.076 Uiso 1 1 calc R U . . .
C52 C 0.4549(3) 0.8207(3) 0.14658(18) 0.0636(7) Uani 1 1 d . U . . .
H52 H 0.5505 0.7771 0.1159 0.076 Uiso 1 1 calc R U . . .
C62 C 0.3530(3) 0.7500(3) 0.17499(16) 0.0532(7) Uani 1 1 d . U . . .
H62 H 0.3803 0.6588 0.1633 0.064 Uiso 1 1 calc R U . . .
C13 C -0.0833(3) 0.8228(3) 0.31745(15) 0.0441(6) Uani 1 1 d . U . . .
C23 C -0.0462(4) 0.8132(3) 0.39973(17) 0.0716(8) Uani 1 1 d . U . . .
H23 H 0.0604 0.7541 0.4205 0.086 Uiso 1 1 calc R U . . .
C33 C -0.1685(5) 0.8920(4) 0.4516(2) 0.0905(10) Uani 1 1 d . U . . .
H33 H -0.1436 0.8868 0.5069 0.109 Uiso 1 1 calc R U . . .
C43 C -0.3251(5) 0.9769(4) 0.4210(2) 0.0816(9) Uani 1 1 d . U . . .
H43 H -0.4068 1.0281 0.4562 0.098 Uiso 1 1 calc R U . . .
C53 C -0.3639(4) 0.9880(4) 0.3406(2) 0.0787(9) Uani 1 1 d . U . . .
H53 H -0.4710 1.0471 0.3205 0.094 Uiso 1 1 calc R U . . .
C63 C -0.2419(3) 0.9103(3) 0.28817(19) 0.0567(7) Uani 1 1 d . U . . .
H63 H -0.2679 0.9177 0.2327 0.068 Uiso 1 1 calc R U . . .
C14 C 0.2355(4) 0.4560(3) 0.52103(16) 0.0531(7) Uani 1 1 d . U . . .
H14 H 0.1215 0.5128 0.5204 0.064 Uiso 1 1 calc R U . . .
C24 C 0.3151(4) 0.3989(3) 0.59778(17) 0.0612(7) Uani 1 1 d . U . . .
H24 H 0.2558 0.4170 0.6474 0.073 Uiso 1 1 calc R U . . .
C34 C 0.4810(4) 0.3162(3) 0.59971(18) 0.0657(8) Uani 1 1 d . U . . .
H34 H 0.5375 0.2755 0.6507 0.079 Uiso 1 1 calc R U . . .
C44 C 0.5646(4) 0.2933(3) 0.52458(17) 0.0591(7) Uani 1 1 d . U . . .
H44 H 0.6789 0.2380 0.5242 0.071 Uiso 1 1 calc R U . . .
C54 C 0.4764(3) 0.3537(3) 0.44988(16) 0.0445(6) Uani 1 1 d . U . . .
C64 C 0.5583(3) 0.3295(3) 0.36906(16) 0.0489(6) Uani 1 1 d . U . . .
H64 H 0.6736 0.2803 0.3666 0.059 Uiso 1 1 calc R U . . .
C15 C 0.5550(3) 0.3472(3) 0.22370(16) 0.0439(6) Uani 1 1 d . U . . .
C25 C 0.7180(3) 0.3243(3) 0.20718(19) 0.0619(7) Uani 1 1 d . U . . .
H25 H 0.7826 0.3272 0.2484 0.074 Uiso 1 1 calc R U . . .
C35 C 0.7869(4) 0.2971(4) 0.1300(2) 0.0757(9) Uani 1 1 d . U . . .
H35 H 0.8981 0.2807 0.1195 0.091 Uiso 1 1 calc R U . . .
C45 C 0.6928(4) 0.2938(4) 0.0685(2) 0.0754(9) Uani 1 1 d . U . . .
H45 H 0.7405 0.2741 0.0167 0.090 Uiso 1 1 calc R U . . .
C55 C 0.5287(4) 0.3196(4) 0.0833(2) 0.0754(9) Uani 1 1 d . U . . .
H55 H 0.4644 0.3190 0.0412 0.090 Uiso 1 1 calc R U . . .
C65 C 0.4580(4) 0.3466(3) 0.16090(18) 0.0600(7) Uani 1 1 d . U . . .
H65 H 0.3463 0.3643 0.1710 0.072 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 N2 2.117(2) . ?
Cu1 N1 2.1230(19) . ?
Cu1 P1 2.1988(7) . ?
Cu1 Br1 2.4379(4) . ?
P1 C13 1.827(3) . ?
P1 C12 1.830(2) . ?
P1 C11 1.830(2) . ?
N1 C14 1.331(3) . ?
N1 C54 1.334(3) . ?
N2 C64 1.269(3) . ?
N2 C15 1.428(3) . ?
C11 C61 1.370(3) . ?
C11 C21 1.392(3) . ?
C21 C31 1.381(4) . ?
C21 H21 0.9300 . ?
C31 C41 1.355(4) . ?
C31 H31 0.9300 . ?
C41 C51 1.362(4) . ?
C41 H41 0.9300 . ?
C51 C61 1.391(3) . ?
C51 H51 0.9300 . ?
C61 H61 0.9300 . ?
C12 C22 1.383(3) . ?
C12 C62 1.386(3) . ?
C22 C32 1.385(4) . ?
C22 H22 0.9300 . ?
C32 C42 1.360(4) . ?
C32 H32 0.9300 . ?
C42 C52 1.371(4) . ?
C42 H42 0.9300 . ?
C52 C62 1.373(4) . ?
C52 H52 0.9300 . ?
C62 H62 0.9300 . ?
C13 C63 1.374(4) . ?
C13 C23 1.378(4) . ?
C23 C33 1.390(4) . ?
C23 H23 0.9300 . ?
C33 C43 1.362(5) . ?
C33 H33 0.9300 . ?
C43 C53 1.349(5) . ?
C43 H43 0.9300 . ?
C53 C63 1.391(4) . ?
C53 H53 0.9300 . ?
C63 H63 0.9300 . ?
C14 C24 1.378(4) . ?
C14 H14 0.9300 . ?
C24 C34 1.353(4) . ?
C24 H24 0.9300 . ?
C34 C44 1.380(4) . ?
C34 H34 0.9300 . ?
C44 C54 1.384(3) . ?
C44 H44 0.9300 . ?
C54 C64 1.458(4) . ?
C64 H64 0.9300 . ?
C15 C25 1.367(4) . ?
C15 C65 1.392(4) . ?
C25 C35 1.375(4) . ?
C25 H25 0.9300 . ?
C35 C45 1.370(4) . ?
C35 H35 0.9300 . ?
C45 C55 1.366(4) . ?
C45 H45 0.9300 . ?
C55 C65 1.385(4) . ?
C55 H55 0.9300 . ?
C65 H65 0.9300 . ?

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
N2 Cu1 N1 79.00(8) . . ?
N2 Cu1 P1 119.58(6) . . ?
N1 Cu1 P1 124.52(6) . . ?
N2 Cu1 Br1 107.42(5) . . ?
N1 Cu1 Br1 102.93(5) . . ?
P1 Cu1 Br1 116.78(2) . . ?
C13 P1 C12 103.80(11) . . ?
C13 P1 C11 104.57(11) . . ?
C12 P1 C11 101.07(11) . . ?
C13 P1 Cu1 112.64(8) . . ?
C12 P1 Cu1 115.47(8) . . ?
C11 P1 Cu1 117.61(8) . . ?
C14 N1 C54 117.2(2) . . ?
C14 N1 Cu1 130.72(18) . . ?
C54 N1 Cu1 111.70(16) . . ?
C64 N2 C15 119.6(2) . . ?
C64 N2 Cu1 112.28(18) . . ?
C15 N2 Cu1 128.14(16) . . ?
C61 C11 C21 118.7(2) . . ?
C61 C11 P1 119.37(19) . . ?
C21 C11 P1 121.9(2) . . ?
C31 C21 C11 120.1(3) . . ?
C31 C21 H21 119.9 . . ?
C11 C21 H21 119.9 . . ?
C41 C31 C21 120.6(3) . . ?
C41 C31 H31 119.7 . . ?
C21 C31 H31 119.7 . . ?
C31 C41 C51 119.9(3) . . ?
C31 C41 H41 120.0 . . ?
C51 C41 H41 120.0 . . ?
C41 C51 C61 120.4(3) . . ?
C41 C51 H51 119.8 . . ?
C61 C51 H51 119.8 . . ?
C11 C61 C51 120.2(3) . . ?
C11 C61 H61 119.9 . . ?
C51 C61 H61 119.9 . . ?
C22 C12 C62 118.1(2) . . ?
C22 C12 P1 124.58(19) . . ?
C62 C12 P1 117.3(2) . . ?
C12 C22 C32 120.6(3) . . ?
C12 C22 H22 119.7 . . ?
C32 C22 H22 119.7 . . ?
C42 C32 C22 120.2(3) . . ?
C42 C32 H32 119.9 . . ?
C22 C32 H32 119.9 . . ?
C32 C42 C52 120.0(3) . . ?
C32 C42 H42 120.0 . . ?
C52 C42 H42 120.0 . . ?
C42 C52 C62 120.2(3) . . ?
C42 C52 H52 119.9 . . ?
C62 C52 H52 119.9 . . ?
C52 C62 C12 120.8(3) . . ?
C52 C62 H62 119.6 . . ?
C12 C62 H62 119.6 . . ?
C63 C13 C23 119.0(3) . . ?
C63 C13 P1 123.9(2) . . ?
C23 C13 P1 117.0(2) . . ?
C13 C23 C33 119.9(3) . . ?
C13 C23 H23 120.1 . . ?
C33 C23 H23 120.1 . . ?
C43 C33 C23 119.7(4) . . ?
C43 C33 H33 120.1 . . ?
C23 C33 H33 120.1 . . ?
C53 C43 C33 121.3(3) . . ?
C53 C43 H43 119.3 . . ?
C33 C43 H43 119.3 . . ?
C43 C53 C63 119.3(4) . . ?
C43 C53 H53 120.4 . . ?
C63 C53 H53 120.4 . . ?
C13 C63 C53 120.7(3) . . ?
C13 C63 H63 119.6 . . ?
C53 C63 H63 119.6 . . ?
N1 C14 C24 123.7(3) . . ?
N1 C14 H14 118.1 . . ?
C24 C14 H14 118.1 . . ?
C34 C24 C14 118.9(3) . . ?
C34 C24 H24 120.6 . . ?
C14 C24 H24 120.6 . . ?
C24 C34 C44 118.7(3) . . ?
C24 C34 H34 120.6 . . ?
C44 C34 H34 120.6 . . ?
C34 C44 C54 119.2(3) . . ?
C34 C44 H44 120.4 . . ?
C54 C44 H44 120.4 . . ?
N1 C54 C44 122.3(3) . . ?
N1 C54 C64 116.4(2) . . ?
C44 C54 C64 121.3(3) . . ?
N2 C64 C54 120.3(2) . . ?
N2 C64 H64 119.8 . . ?
C54 C64 H64 119.8 . . ?
C25 C15 C65 119.4(3) . . ?
C25 C15 N2 124.3(2) . . ?
C65 C15 N2 116.2(2) . . ?
C15 C25 C35 120.3(3) . . ?
C15 C25 H25 119.8 . . ?
C35 C25 H25 119.8 . . ?
C45 C35 C25 120.4(3) . . ?
C45 C35 H35 119.8 . . ?
C25 C35 H35 119.8 . . ?
C55 C45 C35 120.0(3) . . ?
C55 C45 H45 120.0 . . ?
C35 C45 H45 120.0 . . ?
C45 C55 C65 120.1(3) . . ?
C45 C55 H55 120.0 . . ?
C65 C55 H55 120.0 . . ?
C55 C65 C15 119.7(3) . . ?
C55 C65 H65 120.2 . . ?
C15 C65 H65 120.2 . . ?

_refine_diff_density_max         0.730
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.049

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1559219'
# Added during the CSD deposition process: Wednesday 28 June 2017 06:48 PM
# end Validation Reply Form


_audit_update_record             
;
2017-06-28 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_1                   
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          16 Note
RESPONSE: This is due to a large beamstop shadowing (technicians in charge striving for detector preservation???)
;
_vrf_PLAT934_1                   
;
PROBLEM: Number of (Iobs-Icalc)/SigmaW &gt; 10 Outliers ....          2 Check
RESPONSE: No comments
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 Br Cu N3 O2 P'
_chemical_formula_sum            'C30 H24 Br Cu N3 O2 P'

_chemical_formula_weight         632.94

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'
P P 0.1023 0.0942 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'

_cell_length_a                   33.966(2)
_cell_length_b                   9.1945(4)
_cell_length_c                   20.1441(13)
_cell_angle_alpha                90
_cell_angle_beta                 117.499(8)
_cell_angle_gamma                90
_cell_volume                     5580.2(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    3244
_cell_measurement_theta_min      3.782
_cell_measurement_theta_max      26.432

_exptl_crystal_description       fragment
_exptl_crystal_colour            dark_red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             2560
_exptl_transmission_factor_min   0.60
_exptl_transmission_factor_max   0.78
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    2.304
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro (Oxford Diffraction, 2009)'
_diffrn_ambient_temperature      294(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            9502
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.753
_diffrn_reflns_theta_max         28.178
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             5845
_reflns_number_gt                3091
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5845
_refine_ls_number_parameters     343
_refine_ls_number_restraints     318
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1117
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_restrained_S_all      0.924
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.40097(2) 0.38758(6) -0.02797(3) 0.04590(16) Uani 1 1 d . U . . .
Br1 Br 0.40795(2) 0.25938(5) -0.12700(2) 0.05660(16) Uani 1 1 d . U . . .
P1 P 0.34317(3) 0.32786(12) -0.01248(5) 0.0374(3) Uani 1 1 d . U . . .
N1 N 0.40944(10) 0.6089(4) -0.04289(18) 0.0473(8) Uani 1 1 d . U . . .
N2 N 0.46531(10) 0.4236(4) 0.06007(17) 0.0457(8) Uani 1 1 d . U . . .
N3 N 0.56917(19) -0.0189(6) 0.2563(3) 0.0939(15) Uani 1 1 d . U . . .
O1 O 0.55106(15) -0.1277(5) 0.2575(3) 0.1188(15) Uani 1 1 d . U . . .
O2 O 0.61043(15) 0.0004(5) 0.2865(2) 0.1244(15) Uani 1 1 d . U . . .
C11 C 0.32970(12) 0.1350(4) -0.0164(2) 0.0385(8) Uani 1 1 d . U . . .
C21 C 0.35969(13) 0.0443(5) 0.0388(2) 0.0527(11) Uani 1 1 d . U . . .
H21 H 0.3855 0.0837 0.0768 0.063 Uiso 1 1 calc R U . . .
C31 C 0.35200(16) -0.1030(5) 0.0385(3) 0.0660(13) Uani 1 1 d . U . . .
H31 H 0.3726 -0.1622 0.0757 0.079 Uiso 1 1 calc R U . . .
C41 C 0.31403(16) -0.1617(5) -0.0166(3) 0.0672(12) Uani 1 1 d . U . . .
H41 H 0.3087 -0.2610 -0.0168 0.081 Uiso 1 1 calc R U . . .
C51 C 0.28367(16) -0.0741(5) -0.0717(3) 0.0701(13) Uani 1 1 d . U . . .
H51 H 0.2579 -0.1144 -0.1093 0.084 Uiso 1 1 calc R U . . .
C61 C 0.29118(14) 0.0745(5) -0.0715(2) 0.0555(11) Uani 1 1 d . U . . .
H61 H 0.2703 0.1334 -0.1085 0.067 Uiso 1 1 calc R U . . .
C12 C 0.29297(12) 0.4108(4) -0.0861(2) 0.0409(8) Uani 1 1 d . U . . .
C22 C 0.28807(14) 0.4104(6) -0.1578(2) 0.0655(13) Uani 1 1 d . U . . .
H22 H 0.3095 0.3669 -0.1677 0.079 Uiso 1 1 calc R U . . .
C32 C 0.25117(16) 0.4748(7) -0.2156(3) 0.0840(17) Uani 1 1 d . U . . .
H32 H 0.2479 0.4724 -0.2640 0.101 Uiso 1 1 calc R U . . .
C42 C 0.21953(15) 0.5416(6) -0.2023(3) 0.0726(14) Uani 1 1 d . U . . .
H42 H 0.1952 0.5862 -0.2411 0.087 Uiso 1 1 calc R U . . .
C52 C 0.22423(14) 0.5416(5) -0.1317(3) 0.0630(12) Uani 1 1 d . U . . .
H52 H 0.2026 0.5860 -0.1225 0.076 Uiso 1 1 calc R U . . .
C62 C 0.26034(12) 0.4772(5) -0.0731(2) 0.0496(10) Uani 1 1 d . U . . .
H62 H 0.2628 0.4782 -0.0252 0.059 Uiso 1 1 calc R U . . .
C13 C 0.34461(11) 0.3883(4) 0.07476(19) 0.0376(8) Uani 1 1 d . U . . .
C23 C 0.32289(13) 0.3162(5) 0.1095(2) 0.0479(10) Uani 1 1 d . U . . .
H23 H 0.3066 0.2327 0.0876 0.057 Uiso 1 1 calc R U . . .
C33 C 0.32516(14) 0.3667(5) 0.1755(2) 0.0587(11) Uani 1 1 d . U . . .
H33 H 0.3112 0.3163 0.1987 0.070 Uiso 1 1 calc R U . . .
C43 C 0.34855(14) 0.4933(6) 0.2071(2) 0.0630(12) Uani 1 1 d . U . . .
H43 H 0.3495 0.5301 0.2508 0.076 Uiso 1 1 calc R U . . .
C53 C 0.37021(15) 0.5639(5) 0.1739(2) 0.0622(12) Uani 1 1 d . U . . .
H53 H 0.3861 0.6483 0.1954 0.075 Uiso 1 1 calc R U . . .
C63 C 0.36878(13) 0.5117(5) 0.1091(2) 0.0489(10) Uani 1 1 d . U . . .
H63 H 0.3843 0.5599 0.0878 0.059 Uiso 1 1 calc R U . . .
C14 C 0.38168(15) 0.7020(5) -0.0937(3) 0.0600(12) Uani 1 1 d . U . . .
H14 H 0.3535 0.6698 -0.1275 0.072 Uiso 1 1 calc R U . . .
C24 C 0.39322(17) 0.8449(5) -0.0981(3) 0.0719(13) Uani 1 1 d . U . . .
H24 H 0.3732 0.9075 -0.1341 0.086 Uiso 1 1 calc R U . . .
C34 C 0.43489(17) 0.8921(6) -0.0479(3) 0.0790(14) Uani 1 1 d . U . . .
H34 H 0.4434 0.9877 -0.0492 0.095 Uiso 1 1 calc R U . . .
C44 C 0.46334(17) 0.7977(5) 0.0033(3) 0.0685(13) Uani 1 1 d . U . . .
H44 H 0.4917 0.8277 0.0373 0.082 Uiso 1 1 calc R U . . .
C54 C 0.44984(13) 0.6557(5) 0.0048(2) 0.0484(9) Uani 1 1 d . U . . .
C64 C 0.47908(14) 0.5524(5) 0.0597(2) 0.0539(11) Uani 1 1 d . U . . .
H64 H 0.5076 0.5798 0.0944 0.065 Uiso 1 1 calc R U . . .
C15 C 0.49264(13) 0.3190(5) 0.1123(2) 0.0458(9) Uani 1 1 d . U . . .
C25 C 0.53511(15) 0.3464(6) 0.1705(3) 0.0757(15) Uani 1 1 d . U . . .
H25 H 0.5468 0.4399 0.1781 0.091 Uiso 1 1 calc R U . . .
C35 C 0.55922(18) 0.2361(6) 0.2161(3) 0.0885(17) Uani 1 1 d . U . . .
H35 H 0.5877 0.2537 0.2540 0.106 Uiso 1 1 calc R U . . .
C45 C 0.54179(16) 0.1003(6) 0.2064(3) 0.0661(12) Uani 1 1 d . U . . .
C55 C 0.50022(15) 0.0678(6) 0.1501(3) 0.0686(13) Uani 1 1 d . U . . .
H55 H 0.4888 -0.0260 0.1437 0.082 Uiso 1 1 calc R U . . .
C65 C 0.47602(14) 0.1799(5) 0.1033(3) 0.0576(11) Uani 1 1 d . U . . .
H65 H 0.4478 0.1608 0.0648 0.069 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 2.096(3) . ?
Cu1 N2 2.110(3) . ?
Cu1 P1 2.1952(10) . ?
Cu1 Br1 2.4212(7) . ?
P1 C13 1.822(4) . ?
P1 C11 1.824(4) . ?
P1 C12 1.831(4) . ?
N1 C54 1.332(5) . ?
N1 C14 1.334(5) . ?
N2 C64 1.275(5) . ?
N2 C15 1.411(5) . ?
N3 O1 1.181(6) . ?
N3 O2 1.256(6) . ?
N3 C45 1.488(7) . ?
C11 C61 1.383(5) . ?
C11 C21 1.387(5) . ?
C21 C31 1.379(6) . ?
C21 H21 0.9300 . ?
C31 C41 1.365(6) . ?
C31 H31 0.9300 . ?
C41 C51 1.374(6) . ?
C41 H41 0.9300 . ?
C51 C61 1.389(6) . ?
C51 H51 0.9300 . ?
C61 H61 0.9300 . ?
C12 C22 1.376(5) . ?
C12 C62 1.391(5) . ?
C22 C32 1.388(6) . ?
C22 H22 0.9300 . ?
C32 C42 1.366(6) . ?
C32 H32 0.9300 . ?
C42 C52 1.356(6) . ?
C42 H42 0.9300 . ?
C52 C62 1.382(6) . ?
C52 H52 0.9300 . ?
C62 H62 0.9300 . ?
C13 C63 1.384(5) . ?
C13 C23 1.396(5) . ?
C23 C33 1.378(5) . ?
C23 H23 0.9300 . ?
C33 C43 1.387(6) . ?
C33 H33 0.9300 . ?
C43 C53 1.366(6) . ?
C43 H43 0.9300 . ?
C53 C63 1.371(6) . ?
C53 H53 0.9300 . ?
C63 H63 0.9300 . ?
C14 C24 1.385(6) . ?
C14 H14 0.9300 . ?
C24 C34 1.375(7) . ?
C24 H24 0.9300 . ?
C34 C44 1.354(6) . ?
C34 H34 0.9300 . ?
C44 C54 1.389(6) . ?
C44 H44 0.9300 . ?
C54 C64 1.448(6) . ?
C64 H64 0.9300 . ?
C15 C65 1.376(6) . ?
C15 C25 1.400(5) . ?
C25 C35 1.359(7) . ?
C25 H25 0.9300 . ?
C35 C45 1.357(7) . ?
C35 H35 0.9300 . ?
C45 C55 1.375(6) . ?
C55 C65 1.382(6) . ?
C55 H55 0.9300 . ?
C65 H65 0.9300 . ?

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 79.09(13) . . ?
N1 Cu1 P1 117.01(9) . . ?
N2 Cu1 P1 124.54(9) . . ?
N1 Cu1 Br1 106.40(9) . . ?
N2 Cu1 Br1 108.15(9) . . ?
P1 Cu1 Br1 115.44(4) . . ?
C13 P1 C11 103.49(17) . . ?
C13 P1 C12 104.73(17) . . ?
C11 P1 C12 104.39(17) . . ?
C13 P1 Cu1 115.68(12) . . ?
C11 P1 Cu1 117.37(12) . . ?
C12 P1 Cu1 109.89(12) . . ?
C54 N1 C14 118.3(4) . . ?
C54 N1 Cu1 112.0(3) . . ?
C14 N1 Cu1 129.7(3) . . ?
C64 N2 C15 121.4(4) . . ?
C64 N2 Cu1 112.4(3) . . ?
C15 N2 Cu1 126.1(3) . . ?
O1 N3 O2 125.8(6) . . ?
O1 N3 C45 118.0(6) . . ?
O2 N3 C45 115.6(6) . . ?
C61 C11 C21 118.3(4) . . ?
C61 C11 P1 123.5(3) . . ?
C21 C11 P1 118.2(3) . . ?
C31 C21 C11 121.3(4) . . ?
C31 C21 H21 119.4 . . ?
C11 C21 H21 119.4 . . ?
C41 C31 C21 119.9(5) . . ?
C41 C31 H31 120.1 . . ?
C21 C31 H31 120.1 . . ?
C31 C41 C51 120.0(5) . . ?
C31 C41 H41 120.0 . . ?
C51 C41 H41 120.0 . . ?
C41 C51 C61 120.4(5) . . ?
C41 C51 H51 119.8 . . ?
C61 C51 H51 119.8 . . ?
C11 C61 C51 120.1(4) . . ?
C11 C61 H61 119.9 . . ?
C51 C61 H61 119.9 . . ?
C22 C12 C62 118.5(4) . . ?
C22 C12 P1 117.7(3) . . ?
C62 C12 P1 123.7(3) . . ?
C12 C22 C32 120.2(4) . . ?
C12 C22 H22 119.9 . . ?
C32 C22 H22 119.9 . . ?
C42 C32 C22 121.0(5) . . ?
C42 C32 H32 119.5 . . ?
C22 C32 H32 119.5 . . ?
C52 C42 C32 118.8(5) . . ?
C52 C42 H42 120.6 . . ?
C32 C42 H42 120.6 . . ?
C42 C52 C62 121.6(5) . . ?
C42 C52 H52 119.2 . . ?
C62 C52 H52 119.2 . . ?
C52 C62 C12 119.8(4) . . ?
C52 C62 H62 120.1 . . ?
C12 C62 H62 120.1 . . ?
C63 C13 C23 117.9(4) . . ?
C63 C13 P1 118.5(3) . . ?
C23 C13 P1 123.6(3) . . ?
C33 C23 C13 121.1(4) . . ?
C33 C23 H23 119.4 . . ?
C13 C23 H23 119.4 . . ?
C23 C33 C43 119.3(4) . . ?
C23 C33 H33 120.3 . . ?
C43 C33 H33 120.3 . . ?
C53 C43 C33 119.9(4) . . ?
C53 C43 H43 120.1 . . ?
C33 C43 H43 120.1 . . ?
C63 C53 C43 120.7(4) . . ?
C63 C53 H53 119.7 . . ?
C43 C53 H53 119.7 . . ?
C53 C63 C13 121.0(4) . . ?
C53 C63 H63 119.5 . . ?
C13 C63 H63 119.5 . . ?
N1 C14 C24 122.5(5) . . ?
N1 C14 H14 118.8 . . ?
C24 C14 H14 118.8 . . ?
C34 C24 C14 118.6(5) . . ?
C34 C24 H24 120.7 . . ?
C14 C24 H24 120.7 . . ?
C44 C34 C24 119.2(5) . . ?
C44 C34 H34 120.4 . . ?
C24 C34 H34 120.4 . . ?
C34 C44 C54 119.5(5) . . ?
C34 C44 H44 120.2 . . ?
C54 C44 H44 120.2 . . ?
N1 C54 C44 121.9(4) . . ?
N1 C54 C64 117.0(4) . . ?
C44 C54 C64 121.1(4) . . ?
N2 C64 C54 119.3(4) . . ?
N2 C64 H64 120.4 . . ?
C54 C64 H64 120.4 . . ?
C65 C15 C25 118.6(4) . . ?
C65 C15 N2 116.5(4) . . ?
C25 C15 N2 124.8(4) . . ?
C35 C25 C15 119.9(5) . . ?
C35 C25 H25 120.1 . . ?
C15 C25 H25 120.1 . . ?
C45 C35 C25 120.2(5) . . ?
C45 C35 H35 119.9 . . ?
C25 C35 H35 119.9 . . ?
C35 C45 C55 122.1(5) . . ?
C35 C45 N3 119.1(5) . . ?
C55 C45 N3 118.7(5) . . ?
C45 C55 C65 117.5(5) . . ?
C45 C55 H55 121.3 . . ?
C65 C55 H55 121.3 . . ?
C15 C65 C55 121.6(4) . . ?
C15 C65 H65 119.2 . . ?
C55 C65 H65 119.2 . . ?

_refine_diff_density_max         0.612
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.075

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1559218'
# Added during the CSD deposition process: Wednesday 28 June 2017 06:48 PM
# end Validation Reply Form


_audit_update_record             
;
2017-06-28 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_5                   
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          14 Note
RESPONSE: This is due to a large beamstop shadowing (technicians in charge striving for detector preservation???)
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C62 H54 Br2 Cu2 N4 O2 P2'
_chemical_formula_sum            'C62 H54 Br2 Cu2 N4 O2 P2'
_chemical_formula_weight         1235.93

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'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8750(3)
_cell_length_b                   9.9744(3)
_cell_length_c                   15.7009(5)
_cell_angle_alpha                84.458(3)
_cell_angle_beta                 85.700(3)
_cell_angle_gamma                63.811(3)
_cell_volume                     1380.36(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2896
_cell_measurement_theta_min      3.884
_cell_measurement_theta_max      25.217


_exptl_crystal_description       fragment
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   0.60
_exptl_transmission_factor_max   0.60
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    2.323
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro (Oxford Diffraction, 2009)'
_diffrn_ambient_temperature      294(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            23131
_diffrn_reflns_av_unetI/netI     0.0994
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.541
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5396
_reflns_number_gt                2814
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0315P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5396
_refine_ls_number_parameters     335
_refine_ls_number_restraints     309
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0748
_refine_ls_wR_factor_gt          0.0686
_refine_ls_goodness_of_fit_ref   0.859
_refine_ls_restrained_S_all      0.862
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.94293(5) 0.40845(5) 0.20333(3) 0.04412(15) Uani 1 1 d . U . . .
Br1 Br 0.70396(4) 0.63113(4) 0.17795(2) 0.05454(15) Uani 1 1 d . U . . .
P1 P 0.93341(11) 0.26995(10) 0.31933(6) 0.0380(2) Uani 1 1 d . U . . .
O1 O 0.7475(3) 0.0676(3) -0.09803(17) 0.0693(8) Uani 1 1 d . U . . .
N1 N 1.1304(3) 0.4570(3) 0.18353(17) 0.0424(7) Uani 1 1 d . U . . .
N2 N 1.0220(3) 0.3286(3) 0.08183(16) 0.0389(7) Uani 1 1 d . U . . .
C11 C 0.8345(4) 0.1555(4) 0.3096(2) 0.0396(8) Uani 1 1 d . U . . .
C21 C 0.6852(4) 0.2253(5) 0.2857(2) 0.0558(10) Uani 1 1 d . U . . .
H21 H 0.6354 0.3293 0.2813 0.067 Uiso 1 1 calc R U . . .
C31 C 0.6093(5) 0.1456(5) 0.2685(3) 0.0726(12) Uani 1 1 d . U . . .
H31 H 0.5086 0.1955 0.2538 0.087 Uiso 1 1 calc R U . . .
C41 C 0.6808(5) -0.0067(5) 0.2727(3) 0.0760(13) Uani 1 1 d . U . . .
H41 H 0.6305 -0.0609 0.2586 0.091 Uiso 1 1 calc R U . . .
C51 C 0.8266(5) -0.0795(5) 0.2978(3) 0.0734(12) Uani 1 1 d . U . . .
H51 H 0.8746 -0.1837 0.3026 0.088 Uiso 1 1 calc R U . . .
C61 C 0.9034(5) 0.0008(4) 0.3162(2) 0.0575(11) Uani 1 1 d . U . . .
H61 H 1.0027 -0.0500 0.3333 0.069 Uiso 1 1 calc R U . . .
C12 C 1.1176(4) 0.1314(4) 0.3552(2) 0.0423(8) Uani 1 1 d . U . . .
C22 C 1.2176(4) 0.0460(4) 0.2937(3) 0.0562(10) Uani 1 1 d . U . . .
H22 H 1.1909 0.0659 0.2367 0.067 Uiso 1 1 calc R U . . .
C32 C 1.3554(5) -0.0674(5) 0.3148(3) 0.0725(12) Uani 1 1 d . U . . .
H32 H 1.4192 -0.1276 0.2732 0.087 Uiso 1 1 calc R U . . .
C42 C 1.3980(5) -0.0908(5) 0.3983(3) 0.0773(13) Uani 1 1 d . U . . .
H42 H 1.4927 -0.1653 0.4130 0.093 Uiso 1 1 calc R U . . .
C52 C 1.3025(5) -0.0057(5) 0.4597(3) 0.0756(13) Uani 1 1 d . U . . .
H52 H 1.3334 -0.0211 0.5158 0.091 Uiso 1 1 calc R U . . .
C62 C 1.1603(4) 0.1031(4) 0.4397(2) 0.0563(10) Uani 1 1 d . U . . .
H62 H 1.0937 0.1571 0.4825 0.068 Uiso 1 1 calc R U . . .
C13 C 0.8398(4) 0.3764(4) 0.4114(2) 0.0413(9) Uani 1 1 d . U . . .
C23 C 0.7693(6) 0.3273(5) 0.4776(3) 0.0857(16) Uani 1 1 d . U . . .
H23 H 0.7701 0.2338 0.4771 0.103 Uiso 1 1 calc R U . . .
C33 C 0.6973(6) 0.4157(6) 0.5447(3) 0.1064(19) Uani 1 1 d . U . . .
H33 H 0.6495 0.3815 0.5888 0.128 Uiso 1 1 calc R U . . .
C43 C 0.6958(5) 0.5514(5) 0.5471(3) 0.0758(13) Uani 1 1 d . U . . .
H43 H 0.6461 0.6107 0.5922 0.091 Uiso 1 1 calc R U . . .
C53 C 0.7661(5) 0.6001(5) 0.4841(3) 0.0733(13) Uani 1 1 d . U . . .
H53 H 0.7678 0.6922 0.4863 0.088 Uiso 1 1 calc R U . . .
C63 C 0.8363(4) 0.5134(4) 0.4158(2) 0.0587(11) Uani 1 1 d . U . . .
H63 H 0.8822 0.5498 0.3717 0.070 Uiso 1 1 calc R U . . .
C14 C 1.1887(4) 0.5184(4) 0.2334(2) 0.0527(10) Uani 1 1 d . U . . .
H14 H 1.1422 0.5463 0.2868 0.063 Uiso 1 1 calc R U . . .
C24 C 1.3135(4) 0.5424(4) 0.2102(3) 0.0613(11) Uani 1 1 d . U . . .
H24 H 1.3494 0.5866 0.2466 0.074 Uiso 1 1 calc R U . . .
C34 C 1.3841(5) 0.5001(4) 0.1321(3) 0.0629(11) Uani 1 1 d . U . . .
H34 H 1.4691 0.5147 0.1149 0.075 Uiso 1 1 calc R U . . .
C44 C 1.3282(4) 0.4366(4) 0.0804(3) 0.0558(10) Uani 1 1 d . U . . .
H44 H 1.3755 0.4064 0.0275 0.067 Uiso 1 1 calc R U . . .
C54 C 1.2005(4) 0.4167(4) 0.1065(2) 0.0418(8) Uani 1 1 d . U . . .
C64 C 1.1357(4) 0.3511(4) 0.0534(2) 0.0443(9) Uani 1 1 d . U . . .
H64 H 1.1764 0.3252 -0.0013 0.053 Uiso 1 1 calc R U . . .
C15 C 0.9542(4) 0.2636(4) 0.0328(2) 0.0386(8) Uani 1 1 d . U . . .
C25 C 1.0029(4) 0.2151(4) -0.0493(2) 0.0478(9) Uani 1 1 d . U . . .
H25 H 1.0845 0.2265 -0.0766 0.057 Uiso 1 1 calc R U . . .
C35 C 0.9312(4) 0.1513(4) -0.0895(2) 0.0505(9) Uani 1 1 d . U . . .
H35 H 0.9656 0.1180 -0.1438 0.061 Uiso 1 1 calc R U . . .
C45 C 0.8088(4) 0.1349(4) -0.0515(2) 0.0491(9) Uani 1 1 d . U . . .
C55 C 0.7564(4) 0.1841(4) 0.0294(2) 0.0488(9) Uani 1 1 d . U . . .
H55 H 0.6735 0.1741 0.0557 0.059 Uiso 1 1 calc R U . . .
C65 C 0.8298(4) 0.2481(4) 0.0701(2) 0.0433(9) Uani 1 1 d . U . . .
H65 H 0.7947 0.2819 0.1243 0.052 Uiso 1 1 calc R U . . .
C75 C 0.6238(5) 0.0455(5) -0.0603(3) 0.0736(12) Uani 1 1 d . U . . .
H75A H 0.6531 -0.0148 -0.0074 0.110 Uiso 1 1 calc R U . . .
H75B H 0.5929 -0.0044 -0.0986 0.110 Uiso 1 1 calc R U . . .
H75C H 0.5414 0.1407 -0.0494 0.110 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 N2 2.099(3) . ?
Cu1 N1 2.106(3) . ?
Cu1 P1 2.1994(10) . ?
Cu1 Br1 2.4504(6) . ?
P1 C13 1.817(3) . ?
P1 C11 1.822(4) . ?
P1 C12 1.822(4) . ?
O1 C45 1.367(4) . ?
O1 C75 1.413(5) . ?
N1 C14 1.339(4) . ?
N1 C54 1.352(4) . ?
N2 C64 1.280(4) . ?
N2 C15 1.421(4) . ?
C11 C61 1.381(5) . ?
C11 C21 1.388(5) . ?
C21 C31 1.365(5) . ?
C21 H21 0.9300 . ?
C31 C41 1.360(6) . ?
C31 H31 0.9300 . ?
C41 C51 1.365(6) . ?
C41 H41 0.9300 . ?
C51 C61 1.383(5) . ?
C51 H51 0.9300 . ?
C61 H61 0.9300 . ?
C12 C22 1.380(5) . ?
C12 C62 1.388(5) . ?
C22 C32 1.370(5) . ?
C22 H22 0.9300 . ?
C32 C42 1.374(6) . ?
C32 H32 0.9300 . ?
C42 C52 1.362(6) . ?
C42 H42 0.9300 . ?
C52 C62 1.379(5) . ?
C52 H52 0.9300 . ?
C62 H62 0.9300 . ?
C13 C63 1.360(5) . ?
C13 C23 1.377(5) . ?
C23 C33 1.381(5) . ?
C23 H23 0.9300 . ?
C33 C43 1.350(6) . ?
C33 H33 0.9300 . ?
C43 C53 1.341(6) . ?
C43 H43 0.9300 . ?
C53 C63 1.385(5) . ?
C53 H53 0.9300 . ?
C63 H63 0.9300 . ?
C14 C24 1.374(5) . ?
C14 H14 0.9300 . ?
C24 C34 1.370(5) . ?
C24 H24 0.9300 . ?
C34 C44 1.357(5) . ?
C34 H34 0.9300 . ?
C44 C54 1.387(5) . ?
C44 H44 0.9300 . ?
C54 C64 1.446(5) . ?
C64 H64 0.9300 . ?
C15 C65 1.385(5) . ?
C15 C25 1.396(4) . ?
C25 C35 1.359(5) . ?
C25 H25 0.9300 . ?
C35 C45 1.375(5) . ?
C35 H35 0.9300 . ?
C45 C55 1.386(5) . ?
C55 C65 1.377(5) . ?
C55 H55 0.9300 . ?
C65 H65 0.9300 . ?
C75 H75A 0.9600 . ?
C75 H75B 0.9600 . ?
C75 H75C 0.9600 . ?

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
N2 Cu1 N1 79.29(11) . . ?
N2 Cu1 P1 125.13(8) . . ?
N1 Cu1 P1 118.03(8) . . ?
N2 Cu1 Br1 104.88(7) . . ?
N1 Cu1 Br1 112.14(7) . . ?
P1 Cu1 Br1 112.95(3) . . ?
C13 P1 C11 103.83(16) . . ?
C13 P1 C12 105.70(16) . . ?
C11 P1 C12 102.33(16) . . ?
C13 P1 Cu1 114.09(12) . . ?
C11 P1 Cu1 115.43(11) . . ?
C12 P1 Cu1 114.12(12) . . ?
C45 O1 C75 117.5(3) . . ?
C14 N1 C54 117.1(3) . . ?
C14 N1 Cu1 131.2(3) . . ?
C54 N1 Cu1 111.8(2) . . ?
C64 N2 C15 122.3(3) . . ?
C64 N2 Cu1 112.8(3) . . ?
C15 N2 Cu1 124.8(2) . . ?
C61 C11 C21 117.0(4) . . ?
C61 C11 P1 123.8(3) . . ?
C21 C11 P1 118.9(3) . . ?
C31 C21 C11 122.0(4) . . ?
C31 C21 H21 119.0 . . ?
C11 C21 H21 119.0 . . ?
C21 C31 C41 120.1(5) . . ?
C21 C31 H31 120.0 . . ?
C41 C31 H31 120.0 . . ?
C51 C41 C31 119.7(5) . . ?
C51 C41 H41 120.1 . . ?
C31 C41 H41 120.1 . . ?
C41 C51 C61 120.3(4) . . ?
C41 C51 H51 119.8 . . ?
C61 C51 H51 119.8 . . ?
C11 C61 C51 120.9(4) . . ?
C11 C61 H61 119.5 . . ?
C51 C61 H61 119.5 . . ?
C22 C12 C62 118.7(4) . . ?
C22 C12 P1 116.9(3) . . ?
C62 C12 P1 124.3(3) . . ?
C32 C22 C12 121.5(4) . . ?
C32 C22 H22 119.3 . . ?
C12 C22 H22 119.3 . . ?
C22 C32 C42 119.0(4) . . ?
C22 C32 H32 120.5 . . ?
C42 C32 H32 120.5 . . ?
C52 C42 C32 120.4(5) . . ?
C52 C42 H42 119.8 . . ?
C32 C42 H42 119.8 . . ?
C42 C52 C62 120.8(5) . . ?
C42 C52 H52 119.6 . . ?
C62 C52 H52 119.6 . . ?
C52 C62 C12 119.4(4) . . ?
C52 C62 H62 120.3 . . ?
C12 C62 H62 120.3 . . ?
C63 C13 C23 117.3(3) . . ?
C63 C13 P1 119.0(3) . . ?
C23 C13 P1 123.8(3) . . ?
C13 C23 C33 120.6(4) . . ?
C13 C23 H23 119.7 . . ?
C33 C23 H23 119.7 . . ?
C43 C33 C23 120.6(5) . . ?
C43 C33 H33 119.7 . . ?
C23 C33 H33 119.7 . . ?
C53 C43 C33 119.7(4) . . ?
C53 C43 H43 120.1 . . ?
C33 C43 H43 120.1 . . ?
C43 C53 C63 120.0(4) . . ?
C43 C53 H53 120.0 . . ?
C63 C53 H53 120.0 . . ?
C13 C63 C53 121.7(4) . . ?
C13 C63 H63 119.2 . . ?
C53 C63 H63 119.2 . . ?
N1 C14 C24 123.6(4) . . ?
N1 C14 H14 118.2 . . ?
C24 C14 H14 118.2 . . ?
C34 C24 C14 118.7(4) . . ?
C34 C24 H24 120.6 . . ?
C14 C24 H24 120.6 . . ?
C44 C34 C24 119.0(4) . . ?
C44 C34 H34 120.5 . . ?
C24 C34 H34 120.5 . . ?
C34 C44 C54 120.0(4) . . ?
C34 C44 H44 120.0 . . ?
C54 C44 H44 120.0 . . ?
N1 C54 C44 121.6(4) . . ?
N1 C54 C64 116.3(3) . . ?
C44 C54 C64 122.1(3) . . ?
N2 C64 C54 119.8(3) . . ?
N2 C64 H64 120.1 . . ?
C54 C64 H64 120.1 . . ?
C65 C15 C25 118.1(4) . . ?
C65 C15 N2 116.7(3) . . ?
C25 C15 N2 125.2(3) . . ?
C35 C25 C15 120.1(4) . . ?
C35 C25 H25 120.0 . . ?
C15 C25 H25 120.0 . . ?
C25 C35 C45 121.4(4) . . ?
C25 C35 H35 119.3 . . ?
C45 C35 H35 119.3 . . ?
O1 C45 C35 115.8(3) . . ?
O1 C45 C55 124.4(4) . . ?
C35 C45 C55 119.8(4) . . ?
C65 C55 C45 118.6(4) . . ?
C65 C55 H55 120.7 . . ?
C45 C55 H55 120.7 . . ?
C55 C65 C15 122.0(3) . . ?
C55 C65 H65 119.0 . . ?
C15 C65 H65 119.0 . . ?
O1 C75 H75A 109.5 . . ?
O1 C75 H75B 109.5 . . ?
H75A C75 H75B 109.5 . . ?
O1 C75 H75C 109.5 . . ?
H75A C75 H75C 109.5 . . ?
H75B C75 H75C 109.5 . . ?

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.062

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1559220'
# Added during the CSD deposition process: Wednesday 28 June 2017 06:48 PM
# end Validation Reply Form


_audit_update_record             
;
2017-06-28 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_2                   
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          18 Note
RESPONSE: This is due to a large beamstop shadowing (technicians in charge striving for detector preservation???)
;
_vrf_PLAT934_2                   
;
PROBLEM: Number of (Iobs-Icalc)/SigmaW &gt; 10 Outliers ....          2 Check
RESPONSE: No comments
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H27 Br Cu N2 O P'
_chemical_formula_sum            'C32 H27 Br Cu N2 O P'
_chemical_formula_weight         629.97

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'
P P 0.1023 0.0942 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'

_cell_length_a                   34.8404(19)
_cell_length_b                   9.2350(3)
_cell_length_c                   20.3611(10)
_cell_angle_alpha                90
_cell_angle_beta                 118.270(7)
_cell_angle_gamma                90
_cell_volume                     5769.8(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5676
_cell_measurement_theta_min      3.7794
_cell_measurement_theta_max      26.488

_exptl_crystal_description       fragment
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             2560
_exptl_transmission_factor_min   0.68
_exptl_transmission_factor_max   0.78
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    2.225
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro (Oxford Diffraction, 2009)'
_diffrn_ambient_temperature      294(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_measurement_method       'ω scans'

_diffrn_reflns_number            30855
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.745
_diffrn_reflns_theta_max         28.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6893
_reflns_number_gt                3020
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0901P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6893
_refine_ls_number_parameters     344
_refine_ls_number_restraints     318
_refine_ls_R_factor_all          0.1583
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.2071
_refine_ls_wR_factor_gt          0.1866
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.129
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.002

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 0.60081(2) 0.60590(8) 0.52582(4) 0.0692(3) Uani 1 1 d . U . . .
Br1 Br 0.59492(2) 0.73586(7) 0.62409(4) 0.0823(3) Uani 1 1 d . U . . .
P1 P 0.65734(5) 0.66510(16) 0.51226(8) 0.0544(4) Uani 1 1 d . U . . .
O1 O 0.4515(4) 1.1292(12) 0.2431(6) 0.215(4) Uani 1 1 d . U . . .
N1 N 0.59070(18) 0.3854(5) 0.5413(3) 0.0844(14) Uani 1 1 d . U . . .
N2 N 0.53652(16) 0.5761(6) 0.4414(3) 0.0804(13) Uani 1 1 d . U . . .
C11 C 0.65581(17) 0.6108(6) 0.4243(3) 0.0564(12) Uani 1 1 d . U . . .
C21 C 0.6321(2) 0.4861(7) 0.3892(3) 0.0816(18) Uani 1 1 d . U . . .
H21 H 0.6171 0.4350 0.4094 0.098 Uiso 1 1 calc R U . . .
C31 C 0.6313(3) 0.4403(8) 0.3237(4) 0.102(2) Uani 1 1 d . U . . .
H31 H 0.6169 0.3548 0.3014 0.122 Uiso 1 1 calc R U . . .
C41 C 0.6510(3) 0.5166(8) 0.2915(4) 0.101(2) Uani 1 1 d . U . . .
H41 H 0.6489 0.4853 0.2465 0.122 Uiso 1 1 calc R U . . .
C51 C 0.6736(2) 0.6381(8) 0.3239(3) 0.089(2) Uani 1 1 d . U . . .
H51 H 0.6873 0.6900 0.3018 0.107 Uiso 1 1 calc R U . . .
C61 C 0.6762(2) 0.6856(7) 0.3918(3) 0.0683(15) Uani 1 1 d . U . . .
H61 H 0.6919 0.7688 0.4146 0.082 Uiso 1 1 calc R U . . .
C12 C 0.67159(19) 0.8574(6) 0.5194(3) 0.0581(12) Uani 1 1 d . U . . .
C22 C 0.6411(2) 0.9513(7) 0.4687(4) 0.0781(16) Uani 1 1 d . U . . .
H22 H 0.6146 0.9152 0.4325 0.094 Uiso 1 1 calc R U . . .
C32 C 0.6494(3) 1.0987(7) 0.4709(4) 0.095(2) Uani 1 1 d . U . . .
H32 H 0.6285 1.1612 0.4370 0.114 Uiso 1 1 calc R U . . .
C42 C 0.6879(3) 1.1497(8) 0.5226(4) 0.0905(19) Uani 1 1 d . U . . .
H42 H 0.6933 1.2487 0.5245 0.109 Uiso 1 1 calc R U . . .
C52 C 0.7191(3) 1.0617(8) 0.5718(4) 0.097(2) Uani 1 1 d . U . . .
H52 H 0.7460 1.0989 0.6062 0.116 Uiso 1 1 calc R U . . .
C62 C 0.7105(2) 0.9143(7) 0.5705(4) 0.0812(17) Uani 1 1 d . U . . .
H62 H 0.7317 0.8535 0.6051 0.097 Uiso 1 1 calc R U . . .
C13 C 0.70659(19) 0.5813(6) 0.5835(3) 0.0614(12) Uani 1 1 d . U . . .
C23 C 0.73834(19) 0.5172(6) 0.5713(3) 0.0659(14) Uani 1 1 d . U . . .
H23 H 0.7359 0.5203 0.5238 0.079 Uiso 1 1 calc R U . . .
C33 C 0.7737(2) 0.4487(8) 0.6279(4) 0.0875(19) Uani 1 1 d . U . . .
H33 H 0.7946 0.4058 0.6182 0.105 Uiso 1 1 calc R U . . .
C43 C 0.7780(3) 0.4437(9) 0.6968(4) 0.108(2) Uani 1 1 d . U . . .
H43 H 0.8017 0.3957 0.7344 0.130 Uiso 1 1 calc R U . . .
C53 C 0.7482(3) 0.5078(10) 0.7123(4) 0.118(3) Uani 1 1 d . U . . .
H53 H 0.7523 0.5068 0.7608 0.142 Uiso 1 1 calc R U . . .
C63 C 0.7115(2) 0.5751(8) 0.6562(3) 0.094(2) Uani 1 1 d . U . . .
H63 H 0.6906 0.6156 0.6667 0.113 Uiso 1 1 calc R U . . .
C14 C 0.6185(3) 0.2907(8) 0.5916(5) 0.102(2) Uani 1 1 d . U . . .
H14 H 0.6472 0.3194 0.6222 0.122 Uiso 1 1 calc R U . . .
C24 C 0.6059(3) 0.1505(8) 0.5995(6) 0.123(3) Uani 1 1 d . U . . .
H24 H 0.6252 0.0875 0.6358 0.148 Uiso 1 1 calc R U . . .
C34 C 0.5637(3) 0.1100(10) 0.5511(6) 0.130(3) Uani 1 1 d . U . . .
H34 H 0.5546 0.0159 0.5527 0.156 Uiso 1 1 calc R U . . .
C44 C 0.5348(3) 0.2062(9) 0.5007(6) 0.124(3) Uani 1 1 d . U . . .
H44 H 0.5060 0.1799 0.4700 0.148 Uiso 1 1 calc R U . . .
C54 C 0.5498(2) 0.3461(8) 0.4964(5) 0.0931(17) Uani 1 1 d . U . . .
C64 C 0.5209(3) 0.4505(8) 0.4433(5) 0.098(2) Uani 1 1 d . U . . .
H64 H 0.4920 0.4279 0.4113 0.118 Uiso 1 1 calc R U . . .
C15 C 0.5110(2) 0.6829(8) 0.3915(4) 0.0839(16) Uani 1 1 d . U . . .
C25 C 0.4685(3) 0.6535(11) 0.3316(5) 0.144(3) Uani 1 1 d . U . . .
H25 H 0.4561 0.5616 0.3222 0.173 Uiso 1 1 calc R U . . .
C35 C 0.4472(4) 0.7736(12) 0.2886(7) 0.167(5) Uani 1 1 d . U . . .
H35 H 0.4193 0.7584 0.2495 0.200 Uiso 1 1 calc R U . . .
C45 C 0.4626(3) 0.9086(11) 0.2976(4) 0.114(2) Uani 1 1 d . U . . .
C55 C 0.5034(2) 0.9311(9) 0.3564(4) 0.098(2) Uani 1 1 d . U . . .
H55 H 0.5154 1.0235 0.3649 0.118 Uiso 1 1 calc R U . . .
C65 C 0.5263(2) 0.8222(8) 0.4020(4) 0.0871(18) Uani 1 1 d . U . . .
H65 H 0.5536 0.8422 0.4420 0.105 Uiso 1 1 calc R U . . .
C75 C 0.4345(5) 1.0286(17) 0.2488(7) 0.170(4) Uani 1 1 d . U . . .
C85 C 0.3870(5) 1.0092(15) 0.2150(8) 0.234(6) Uani 1 1 d . U . . .
H85A H 0.3797 0.9750 0.2522 0.350 Uiso 1 1 calc R U . . .
H85B H 0.3776 0.9398 0.1753 0.350 Uiso 1 1 calc R U . . .
H85C H 0.3728 1.1001 0.1956 0.350 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 N2 2.098(5) . ?
Cu1 N1 2.115(5) . ?
Cu1 P1 2.1838(15) . ?
Cu1 Br1 2.4238(10) . ?
P1 C13 1.814(6) . ?
P1 C12 1.831(6) . ?
P1 C11 1.837(5) . ?
O1 C75 1.135(16) . ?
N1 C14 1.347(9) . ?
N1 C54 1.329(9) . ?
N2 C64 1.288(8) . ?
N2 C15 1.393(8) . ?
C11 C61 1.364(7) . ?
C11 C21 1.400(7) . ?
C21 C31 1.389(9) . ?
C21 H21 0.9300 . ?
C31 C41 1.350(9) . ?
C31 H31 0.9300 . ?
C41 C51 1.350(9) . ?
C41 H41 0.9300 . ?
C51 C61 1.412(8) . ?
C51 H51 0.9300 . ?
C61 H61 0.9300 . ?
C12 C62 1.364(8) . ?
C12 C22 1.380(8) . ?
C22 C32 1.388(9) . ?
C22 H22 0.9300 . ?
C32 C42 1.339(9) . ?
C32 H32 0.9300 . ?
C42 C52 1.346(10) . ?
C42 H42 0.9300 . ?
C52 C62 1.391(9) . ?
C52 H52 0.9300 . ?
C62 H62 0.9300 . ?
C13 C23 1.377(8) . ?
C13 C63 1.408(8) . ?
C23 C33 1.379(8) . ?
C23 H23 0.9300 . ?
C33 C43 1.338(9) . ?
C33 H33 0.9300 . ?
C43 C53 1.356(10) . ?
C43 H43 0.9300 . ?
C53 C63 1.393(10) . ?
C53 H53 0.9300 . ?
C63 H63 0.9300 . ?
C14 C24 1.401(10) . ?
C14 H14 0.9300 . ?
C24 C34 1.381(12) . ?
C24 H24 0.9300 . ?
C34 C44 1.369(12) . ?
C34 H34 0.9300 . ?
C44 C54 1.412(10) . ?
C44 H44 0.9300 . ?
C54 C64 1.442(10) . ?
C64 H64 0.9300 . ?
C15 C65 1.371(10) . ?
C15 C25 1.429(10) . ?
C25 C35 1.390(13) . ?
C25 H25 0.9300 . ?
C35 C45 1.335(12) . ?
C35 H35 0.9300 . ?
C45 C55 1.372(10) . ?
C45 C75 1.501(14) . ?
C55 C65 1.345(9) . ?
C55 H55 0.9300 . ?
C65 H65 0.9300 . ?
C75 C85 1.472(19) . ?
C85 H85A 0.9600 . ?
C85 H85B 0.9600 . ?
C85 H85C 0.9600 . ?

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
N2 Cu1 N1 78.9(2) . . ?
N2 Cu1 P1 127.32(15) . . ?
N1 Cu1 P1 118.92(15) . . ?
N2 Cu1 Br1 105.44(14) . . ?
N1 Cu1 Br1 105.57(15) . . ?
P1 Cu1 Br1 114.48(5) . . ?
C13 P1 C12 103.4(3) . . ?
C13 P1 C11 104.0(3) . . ?
C12 P1 C11 102.9(2) . . ?
C13 P1 Cu1 111.12(18) . . ?
C12 P1 Cu1 117.37(18) . . ?
C11 P1 Cu1 116.34(18) . . ?
C14 N1 C54 119.8(6) . . ?
C14 N1 Cu1 128.9(5) . . ?
C54 N1 Cu1 111.1(5) . . ?
C64 N2 C15 121.8(6) . . ?
C64 N2 Cu1 113.3(5) . . ?
C15 N2 Cu1 124.8(4) . . ?
C61 C11 C21 119.2(5) . . ?
C61 C11 P1 123.5(4) . . ?
C21 C11 P1 117.3(4) . . ?
C11 C21 C31 118.5(6) . . ?
C11 C21 H21 120.7 . . ?
C31 C21 H21 120.7 . . ?
C41 C31 C21 121.7(7) . . ?
C41 C31 H31 119.1 . . ?
C21 C31 H31 119.1 . . ?
C31 C41 C51 120.5(7) . . ?
C31 C41 H41 119.7 . . ?
C51 C41 H41 119.7 . . ?
C41 C51 C61 119.3(7) . . ?
C41 C51 H51 120.3 . . ?
C61 C51 H51 120.3 . . ?
C11 C61 C51 120.6(6) . . ?
C11 C61 H61 119.7 . . ?
C51 C61 H61 119.7 . . ?
C62 C12 C22 117.5(6) . . ?
C62 C12 P1 124.7(5) . . ?
C22 C12 P1 117.8(4) . . ?
C12 C22 C32 121.2(6) . . ?
C12 C22 H22 119.4 . . ?
C32 C22 H22 119.4 . . ?
C42 C32 C22 119.1(7) . . ?
C42 C32 H32 120.4 . . ?
C22 C32 H32 120.4 . . ?
C32 C42 C52 121.8(7) . . ?
C32 C42 H42 119.1 . . ?
C52 C42 H42 119.1 . . ?
C42 C52 C62 119.1(7) . . ?
C42 C52 H52 120.4 . . ?
C62 C52 H52 120.4 . . ?
C12 C62 C52 121.3(7) . . ?
C12 C62 H62 119.4 . . ?
C52 C62 H62 119.4 . . ?
C23 C13 C63 117.6(6) . . ?
C23 C13 P1 125.1(4) . . ?
C63 C13 P1 117.1(5) . . ?
C13 C23 C33 121.4(6) . . ?
C13 C23 H23 119.3 . . ?
C33 C23 H23 119.3 . . ?
C43 C33 C23 120.4(7) . . ?
C43 C33 H33 119.8 . . ?
C23 C33 H33 119.8 . . ?
C33 C43 C53 120.6(8) . . ?
C33 C43 H43 119.7 . . ?
C53 C43 H43 119.7 . . ?
C43 C53 C63 120.7(7) . . ?
C43 C53 H53 119.7 . . ?
C63 C53 H53 119.7 . . ?
C13 C63 C53 119.2(7) . . ?
C13 C63 H63 120.4 . . ?
C53 C63 H63 120.4 . . ?
N1 C14 C24 122.4(8) . . ?
N1 C14 H14 118.8 . . ?
C24 C14 H14 118.8 . . ?
C34 C24 C14 117.0(9) . . ?
C34 C24 H24 121.5 . . ?
C14 C24 H24 121.5 . . ?
C24 C34 C44 121.0(9) . . ?
C24 C34 H34 119.5 . . ?
C44 C34 H34 119.5 . . ?
C34 C44 C54 118.6(9) . . ?
C34 C44 H44 120.7 . . ?
C54 C44 H44 120.7 . . ?
N1 C54 C44 120.9(8) . . ?
N1 C54 C64 118.2(6) . . ?
C44 C54 C64 120.8(7) . . ?
N2 C64 C54 118.1(7) . . ?
N2 C64 H64 121.0 . . ?
C54 C64 H64 121.0 . . ?
C65 C15 N2 118.9(6) . . ?
C65 C15 C25 118.8(8) . . ?
N2 C15 C25 122.2(7) . . ?
C35 C25 C15 114.4(9) . . ?
C35 C25 H25 122.8 . . ?
C15 C25 H25 122.8 . . ?
C45 C35 C25 126.8(10) . . ?
C45 C35 H35 116.6 . . ?
C25 C35 H35 116.6 . . ?
C35 C45 C55 116.4(9) . . ?
C35 C45 C75 120.3(11) . . ?
C55 C45 C75 123.1(11) . . ?
C65 C55 C45 121.4(9) . . ?
C65 C55 H55 119.3 . . ?
C45 C55 H55 119.3 . . ?
C55 C65 C15 122.2(7) . . ?
C55 C65 H65 118.9 . . ?
C15 C65 H65 118.9 . . ?
O1 C75 C85 125.2(14) . . ?
O1 C75 C45 117.7(15) . . ?
C85 C75 C45 117.1(13) . . ?
C75 C85 H85A 109.5 . . ?
C75 C85 H85B 109.5 . . ?
H85A C85 H85B 109.5 . . ?
C75 C85 H85C 109.5 . . ?
H85A C85 H85C 109.5 . . ?
H85B C85 H85C 109.5 . . ?

_refine_diff_density_max         1.046
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.083

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6
_database_code_depnum_ccdc_archive 'CCDC 1559221'
#Added by publCIF



_audit_update_record             
;
2017-06-28 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_6                   
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          19 Note
RESPONSE: This is due to a large beamstop shadowing (technicians in charge striving for detector preservation???)
;
# Added during the CSD deposition process: Wednesday 28 June 2017 06:48 PM
# end Validation Reply Form



_cell_special_details            ?
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H30 Br Cu N3 P'
_chemical_formula_sum            'C32 H30 Br Cu N3 P'
_chemical_formula_weight         631.01

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'
P P 0.1023 0.0942 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   9.36873(18)
_cell_length_b                   12.5828(3)
_cell_length_c                   25.2196(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.584(2)
_cell_angle_gamma                90
_cell_volume                     2947.00(11)
_cell_formula_units_Z            4

_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4776
_cell_measurement_theta_min      3.880
_cell_measurement_theta_max      25.664

_exptl_crystal_description       fragments
_exptl_crystal_colour            dark_red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   0.58
_exptl_transmission_factor_max   0.70
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    2.177
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro (Oxford Diffraction, 2009)'
_diffrn_ambient_temperature      294(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_measurement_method       'ω scans'

_diffrn_reflns_number            25850
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.851
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5779
_reflns_number_gt                4150
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0396P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5779
_refine_ls_number_parameters     345
_refine_ls_number_restraints     318
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0753
_refine_ls_wR_factor_gt          0.0722
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.37415(3) 0.10738(2) 0.39052(2) 0.04178(10) Uani 1 1 d . U . . .
Br1 Br 0.22007(3) -0.04349(2) 0.37753(2) 0.05164(10) Uani 1 1 d . U . . .
P1 P 0.36136(6) 0.24762(5) 0.33868(2) 0.03792(15) Uani 1 1 d . U . . .
N1 N 0.59425(19) 0.06836(15) 0.40290(8) 0.0410(5) Uani 1 1 d . U . . .
N2 N 0.42473(18) 0.14754(15) 0.47171(7) 0.0367(4) Uani 1 1 d . U . . .
N3 N 0.0204(3) 0.3123(2) 0.59626(11) 0.0825(8) Uani 1 1 d . U . . .
C11 C 0.4698(3) 0.3525(2) 0.37364(9) 0.0435(5) Uani 1 1 d . U . . .
C21 C 0.6184(3) 0.3446(2) 0.37984(11) 0.0581(7) Uani 1 1 d . U . . .
H21 H 0.6618 0.2900 0.3629 0.070 Uiso 1 1 calc R U . . .
C31 C 0.7036(4) 0.4178(3) 0.41123(13) 0.0775(9) Uani 1 1 d . U . . .
H31 H 0.8034 0.4128 0.4149 0.093 Uiso 1 1 calc R U . . .
C41 C 0.6389(4) 0.4972(3) 0.43663(13) 0.0794(9) Uani 1 1 d . U . . .
H41 H 0.6953 0.5465 0.4574 0.095 Uiso 1 1 calc R U . . .
C51 C 0.4933(4) 0.5047(3) 0.43182(12) 0.0748(8) Uani 1 1 d . U . . .
H51 H 0.4507 0.5584 0.4496 0.090 Uiso 1 1 calc R U . . .
C61 C 0.4086(3) 0.4330(2) 0.40076(10) 0.0581(7) Uani 1 1 d . U . . .
H61 H 0.3089 0.4386 0.3979 0.070 Uiso 1 1 calc R U . . .
C12 C 0.4396(2) 0.22826(19) 0.27660(9) 0.0383(5) Uani 1 1 d . U . . .
C22 C 0.5112(3) 0.3055(2) 0.25186(10) 0.0586(7) Uani 1 1 d . U . . .
H22 H 0.5228 0.3729 0.2670 0.070 Uiso 1 1 calc R U . . .
C32 C 0.5662(3) 0.2838(3) 0.20469(11) 0.0687(8) Uani 1 1 d . U . . .
H32 H 0.6147 0.3365 0.1883 0.082 Uiso 1 1 calc R U . . .
C42 C 0.5495(3) 0.1870(3) 0.18255(11) 0.0656(7) Uani 1 1 d . U . . .
H42 H 0.5891 0.1724 0.1514 0.079 Uiso 1 1 calc R U . . .
C52 C 0.4756(3) 0.1102(3) 0.20493(11) 0.0688(8) Uani 1 1 d . U . . .
H52 H 0.4610 0.0444 0.1883 0.083 Uiso 1 1 calc R U . . .
C62 C 0.4221(3) 0.1296(2) 0.25261(10) 0.0547(7) Uani 1 1 d . U . . .
H62 H 0.3742 0.0761 0.2685 0.066 Uiso 1 1 calc R U . . .
C13 C 0.1890(2) 0.3091(2) 0.31389(9) 0.0449(6) Uani 1 1 d . U . . .
C23 C 0.1755(3) 0.4062(2) 0.28812(11) 0.0639(7) Uani 1 1 d . U . . .
H23 H 0.2573 0.4464 0.2852 0.077 Uiso 1 1 calc R U . . .
C33 C 0.0422(4) 0.4444(3) 0.26659(13) 0.0798(9) Uani 1 1 d . U . . .
H33 H 0.0343 0.5094 0.2489 0.096 Uiso 1 1 calc R U . . .
C43 C -0.0776(4) 0.3858(3) 0.27153(14) 0.0890(10) Uani 1 1 d . U . . .
H43 H -0.1676 0.4125 0.2579 0.107 Uiso 1 1 calc R U . . .
C53 C -0.0683(3) 0.2890(3) 0.29597(14) 0.0868(10) Uani 1 1 d . U . . .
H53 H -0.1508 0.2488 0.2979 0.104 Uiso 1 1 calc R U . . .
C63 C 0.0663(3) 0.2510(3) 0.31806(11) 0.0630(8) Uani 1 1 d . U . . .
H63 H 0.0733 0.1859 0.3357 0.076 Uiso 1 1 calc R U . . .
C14 C 0.6824(3) 0.0359(2) 0.36826(11) 0.0530(7) Uani 1 1 d . U . . .
H14 H 0.6428 0.0196 0.3335 0.064 Uiso 1 1 calc R U . . .
C24 C 0.8281(3) 0.0259(2) 0.38196(12) 0.0579(7) Uani 1 1 d . U . . .
H24 H 0.8856 0.0039 0.3566 0.069 Uiso 1 1 calc R U . . .
C34 C 0.8882(3) 0.0482(2) 0.43273(12) 0.0622(7) Uani 1 1 d . U . . .
H34 H 0.9870 0.0418 0.4426 0.075 Uiso 1 1 calc R U . . .
C44 C 0.8006(3) 0.0803(2) 0.46926(11) 0.0578(7) Uani 1 1 d . U . . .
H44 H 0.8390 0.0948 0.5044 0.069 Uiso 1 1 calc R U . . .
C54 C 0.6541(2) 0.0909(2) 0.45305(10) 0.0418(5) Uani 1 1 d . U . . .
C64 C 0.5573(2) 0.1307(2) 0.48932(10) 0.0435(6) Uani 1 1 d . U . . .
H64 H 0.5917 0.1437 0.5250 0.052 Uiso 1 1 calc R U . . .
C15 C 0.3276(2) 0.18910(18) 0.50523(9) 0.0382(5) Uani 1 1 d . U . . .
C25 C 0.3536(3) 0.1935(2) 0.56036(9) 0.0456(6) Uani 1 1 d . U . . .
H25 H 0.4414 0.1696 0.5779 0.055 Uiso 1 1 calc R U . . .
C35 C 0.2526(3) 0.2325(2) 0.58958(11) 0.0557(7) Uani 1 1 d . U . . .
H35 H 0.2726 0.2329 0.6267 0.067 Uiso 1 1 calc R U . . .
C45 C 0.1200(3) 0.2718(2) 0.56553(11) 0.0535(6) Uani 1 1 d . U . . .
C55 C 0.0955(3) 0.2676(2) 0.51035(11) 0.0599(7) Uani 1 1 d . U . . .
H55 H 0.0090 0.2932 0.4927 0.072 Uiso 1 1 calc R U . . .
C65 C 0.1959(2) 0.2264(2) 0.48090(10) 0.0521(7) Uani 1 1 d . U . . .
H65 H 0.1750 0.2235 0.4438 0.063 Uiso 1 1 calc R U . . .
C75 C 0.0396(4) 0.3017(4) 0.65361(14) 0.1081(13) Uani 1 1 d . U . . .
H75A H 0.0594 0.2288 0.6631 0.162 Uiso 1 1 calc R U . . .
H75B H -0.0466 0.3240 0.6672 0.162 Uiso 1 1 calc R U . . .
H75C H 0.1187 0.3454 0.6687 0.162 Uiso 1 1 calc R U . . .
C85 C -0.1154(4) 0.3504(4) 0.57179(16) 0.1128(14) Uani 1 1 d . U . . .
H85A H -0.1010 0.4064 0.5472 0.169 Uiso 1 1 calc R U . . .
H85B H -0.1692 0.3771 0.5988 0.169 Uiso 1 1 calc R U . . .
H85C H -0.1678 0.2934 0.5528 0.169 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 2.1026(18) . ?
Cu1 N2 2.1015(18) . ?
Cu1 P1 2.1900(7) . ?
Cu1 Br1 2.3812(4) . ?
P1 C11 1.820(2) . ?
P1 C13 1.825(2) . ?
P1 C12 1.831(2) . ?
N1 C54 1.344(3) . ?
N1 C14 1.342(3) . ?
N2 C64 1.281(3) . ?
N2 C15 1.421(3) . ?
N3 C45 1.386(3) . ?
N3 C85 1.423(4) . ?
N3 C75 1.440(4) . ?
C11 C21 1.383(3) . ?
C11 C61 1.389(4) . ?
C21 C31 1.395(4) . ?
C21 H21 0.9300 . ?
C31 C41 1.371(5) . ?
C31 H31 0.9300 . ?
C41 C51 1.356(4) . ?
C41 H41 0.9300 . ?
C51 C61 1.376(4) . ?
C51 H51 0.9300 . ?
C61 H61 0.9300 . ?
C12 C22 1.377(3) . ?
C12 C62 1.381(3) . ?
C22 C32 1.384(4) . ?
C22 H22 0.9300 . ?
C32 C42 1.341(4) . ?
C32 H32 0.9300 . ?
C42 C52 1.355(4) . ?
C42 H42 0.9300 . ?
C52 C62 1.384(4) . ?
C52 H52 0.9300 . ?
C62 H62 0.9300 . ?
C13 C63 1.379(4) . ?
C13 C23 1.381(4) . ?
C23 C33 1.380(4) . ?
C23 H23 0.9300 . ?
C33 C43 1.362(5) . ?
C33 H33 0.9300 . ?
C43 C53 1.363(5) . ?
C43 H43 0.9300 . ?
C53 C63 1.395(4) . ?
C53 H53 0.9300 . ?
C63 H63 0.9300 . ?
C14 C24 1.369(3) . ?
C14 H14 0.9300 . ?
C24 C34 1.358(4) . ?
C24 H24 0.9300 . ?
C34 C44 1.373(4) . ?
C34 H34 0.9300 . ?
C44 C54 1.385(3) . ?
C44 H44 0.9300 . ?
C54 C64 1.459(3) . ?
C64 H64 0.9300 . ?
C15 C25 1.381(3) . ?
C15 C65 1.385(3) . ?
C25 C35 1.365(3) . ?
C25 H25 0.9300 . ?
C35 C45 1.399(4) . ?
C35 H35 0.9300 . ?
C45 C55 1.381(4) . ?
C55 C65 1.374(3) . ?
C55 H55 0.9300 . ?
C65 H65 0.9300 . ?
C75 H75A 0.9600 . ?
C75 H75B 0.9600 . ?
C75 H75C 0.9600 . ?
C85 H85A 0.9600 . ?
C85 H85B 0.9600 . ?
C85 H85C 0.9600 . ?

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 79.68(7) . . ?
N1 Cu1 P1 104.60(5) . . ?
N2 Cu1 P1 112.05(6) . . ?
N1 Cu1 Br1 113.52(6) . . ?
N2 Cu1 Br1 112.36(5) . . ?
P1 Cu1 Br1 125.16(2) . . ?
C11 P1 C13 105.70(12) . . ?
C11 P1 C12 104.46(11) . . ?
C13 P1 C12 101.51(10) . . ?
C11 P1 Cu1 108.17(8) . . ?
C13 P1 Cu1 121.50(9) . . ?
C12 P1 Cu1 114.00(8) . . ?
C54 N1 C14 117.4(2) . . ?
C54 N1 Cu1 111.71(15) . . ?
C14 N1 Cu1 130.54(17) . . ?
C64 N2 C15 121.53(19) . . ?
C64 N2 Cu1 112.43(15) . . ?
C15 N2 Cu1 126.04(14) . . ?
C45 N3 C85 120.7(3) . . ?
C45 N3 C75 121.6(3) . . ?
C85 N3 C75 116.9(3) . . ?
C21 C11 C61 118.1(2) . . ?
C21 C11 P1 119.5(2) . . ?
C61 C11 P1 121.8(2) . . ?
C11 C21 C31 120.6(3) . . ?
C11 C21 H21 119.7 . . ?
C31 C21 H21 119.7 . . ?
C41 C31 C21 119.4(3) . . ?
C41 C31 H31 120.3 . . ?
C21 C31 H31 120.3 . . ?
C51 C41 C31 120.7(3) . . ?
C51 C41 H41 119.7 . . ?
C31 C41 H41 119.7 . . ?
C41 C51 C61 120.2(3) . . ?
C41 C51 H51 119.9 . . ?
C61 C51 H51 119.9 . . ?
C51 C61 C11 120.9(3) . . ?
C51 C61 H61 119.5 . . ?
C11 C61 H61 119.5 . . ?
C22 C12 C62 118.2(2) . . ?
C22 C12 P1 124.6(2) . . ?
C62 C12 P1 117.17(18) . . ?
C12 C22 C32 120.6(3) . . ?
C12 C22 H22 119.7 . . ?
C32 C22 H22 119.7 . . ?
C42 C32 C22 120.0(3) . . ?
C42 C32 H32 120.0 . . ?
C22 C32 H32 120.0 . . ?
C32 C42 C52 120.9(3) . . ?
C32 C42 H42 119.6 . . ?
C52 C42 H42 119.6 . . ?
C42 C52 C62 119.9(3) . . ?
C42 C52 H52 120.0 . . ?
C62 C52 H52 120.0 . . ?
C12 C62 C52 120.3(3) . . ?
C12 C62 H62 119.9 . . ?
C52 C62 H62 119.9 . . ?
C63 C13 C23 118.7(2) . . ?
C63 C13 P1 117.2(2) . . ?
C23 C13 P1 124.0(2) . . ?
C13 C23 C33 121.0(3) . . ?
C13 C23 H23 119.5 . . ?
C33 C23 H23 119.5 . . ?
C43 C33 C23 119.3(3) . . ?
C43 C33 H33 120.3 . . ?
C23 C33 H33 120.3 . . ?
C53 C43 C33 121.4(3) . . ?
C53 C43 H43 119.3 . . ?
C33 C43 H43 119.3 . . ?
C43 C53 C63 119.2(3) . . ?
C43 C53 H53 120.4 . . ?
C63 C53 H53 120.4 . . ?
C13 C63 C53 120.4(3) . . ?
C13 C63 H63 119.8 . . ?
C53 C63 H63 119.8 . . ?
N1 C14 C24 122.9(3) . . ?
N1 C14 H14 118.6 . . ?
C24 C14 H14 118.6 . . ?
C34 C24 C14 119.6(3) . . ?
C34 C24 H24 120.2 . . ?
C14 C24 H24 120.2 . . ?
C24 C34 C44 118.9(2) . . ?
C24 C34 H34 120.6 . . ?
C44 C34 H34 120.6 . . ?
C34 C44 C54 119.1(3) . . ?
C34 C44 H44 120.4 . . ?
C54 C44 H44 120.4 . . ?
N1 C54 C44 122.1(2) . . ?
N1 C54 C64 116.4(2) . . ?
C44 C54 C64 121.4(2) . . ?
N2 C64 C54 119.6(2) . . ?
N2 C64 H64 120.2 . . ?
C54 C64 H64 120.2 . . ?
C25 C15 C65 117.5(2) . . ?
C25 C15 N2 124.9(2) . . ?
C65 C15 N2 117.6(2) . . ?
C35 C25 C15 121.0(2) . . ?
C35 C25 H25 119.5 . . ?
C15 C25 H25 119.5 . . ?
C25 C35 C45 122.2(3) . . ?
C25 C35 H35 118.9 . . ?
C45 C35 H35 118.9 . . ?
N3 C45 C55 122.9(3) . . ?
N3 C45 C35 120.8(3) . . ?
C55 C45 C35 116.3(2) . . ?
C65 C55 C45 121.7(2) . . ?
C65 C55 H55 119.2 . . ?
C45 C55 H55 119.2 . . ?
C55 C65 C15 121.4(2) . . ?
C55 C65 H65 119.3 . . ?
C15 C65 H65 119.3 . . ?
N3 C75 H75A 109.5 . . ?
N3 C75 H75B 109.5 . . ?
H75A C75 H75B 109.5 . . ?
N3 C75 H75C 109.5 . . ?
H75A C75 H75C 109.5 . . ?
H75B C75 H75C 109.5 . . ?
N3 C85 H85A 109.5 . . ?
N3 C85 H85B 109.5 . . ?
H85A C85 H85B 109.5 . . ?
N3 C85 H85C 109.5 . . ?
H85A C85 H85C 109.5 . . ?
H85B C85 H85C 109.5 . . ?

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.048

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1559222'
# Added during the CSD deposition process: Wednesday 28 June 2017 06:48 PM
# end Validation Reply Form


_audit_update_record             
;
2017-06-28 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_4                   
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          14 Note
RESPONSE: This is due to a large beamstop shadowing (technicians in charge striving for detector preservation???)
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H27 Br Cu N2 P'
_chemical_formula_sum            'C31 H27 Br Cu N2 P'
_chemical_formula_weight         601.96

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'
P P 0.1023 0.0942 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'

_cell_length_a                   34.1246(18)
_cell_length_b                   9.3360(3)
_cell_length_c                   20.2331(9)
_cell_angle_alpha                90
_cell_angle_beta                 119.101(7)
_cell_angle_gamma                90
_cell_volume                     5632.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4654
_cell_measurement_theta_min      3.766
_cell_measurement_theta_max      25.664

_exptl_crystal_description       fragments
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             2448
_exptl_transmission_factor_min   0.682
_exptl_transmission_factor_max   0.7
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    2.273
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro (Oxford Diffraction, 2009)'
_diffrn_ambient_temperature      294(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            16074
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.548
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5530
_reflns_number_gt                2806
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0291P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5530
_refine_ls_number_parameters     326
_refine_ls_number_restraints     303
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0728
_refine_ls_wR_factor_gt          0.0679
_refine_ls_goodness_of_fit_ref   0.832
_refine_ls_restrained_S_all      0.837
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000

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 0.39797(2) 0.12073(5) 0.46323(2) 0.04818(14) Uani 1 1 d . U . . .
Br2 Br 0.40573(2) 0.24875(4) 0.36606(2) 0.05999(13) Uani 1 1 d . U . . .
P1 P 0.34099(3) 0.17825(10) 0.47901(4) 0.0398(2) Uani 1 1 d . U . . .
N1 N 0.40610(10) -0.0969(3) 0.44718(15) 0.0494(7) Uani 1 1 d . U . . .
N2 N 0.46230(9) 0.0825(3) 0.55454(14) 0.0467(7) Uani 1 1 d . U . . .
C11 C 0.28947(10) 0.0939(4) 0.40741(16) 0.0417(8) Uani 1 1 d . U . . .
C21 C 0.28154(13) 0.0943(5) 0.33239(18) 0.0708(12) Uani 1 1 d . U . . .
H21 H 0.3016 0.1386 0.3203 0.085 Uiso 1 1 calc R U . . .
C31 C 0.24349(14) 0.0279(5) 0.2768(2) 0.0873(14) Uani 1 1 d . U . . .
H31 H 0.2378 0.0305 0.2270 0.105 Uiso 1 1 calc R U . . .
C41 C 0.21412(14) -0.0410(5) 0.2932(2) 0.0809(13) Uani 1 1 d . U . . .
H41 H 0.1894 -0.0883 0.2553 0.097 Uiso 1 1 calc R U . . .
C51 C 0.22120(13) -0.0400(4) 0.3654(2) 0.0665(11) Uani 1 1 d . U . . .
H51 H 0.2008 -0.0845 0.3767 0.080 Uiso 1 1 calc R U . . .
C61 C 0.25860(11) 0.0271(4) 0.42195(19) 0.0500(9) Uani 1 1 d . U . . .
H61 H 0.2630 0.0269 0.4711 0.060 Uiso 1 1 calc R U . . .
C12 C 0.34501(10) 0.1188(4) 0.56858(15) 0.0396(7) Uani 1 1 d . U . . .
C22 C 0.36698(12) -0.0085(4) 0.59926(18) 0.0571(10) Uani 1 1 d . U . . .
H22 H 0.3796 -0.0595 0.5749 0.069 Uiso 1 1 calc R U . . .
C32 C 0.37042(13) -0.0609(4) 0.66543(19) 0.0697(11) Uani 1 1 d . U . . .
H32 H 0.3842 -0.1486 0.6845 0.084 Uiso 1 1 calc R U . . .
C42 C 0.35346(13) 0.0162(4) 0.7029(2) 0.0669(11) Uani 1 1 d . U . . .
H42 H 0.3564 -0.0182 0.7482 0.080 Uiso 1 1 calc R U . . .
C52 C 0.33229(12) 0.1433(4) 0.67465(18) 0.0612(10) Uani 1 1 d . U . . .
H52 H 0.3211 0.1954 0.7009 0.073 Uiso 1 1 calc R U . . .
C62 C 0.32739(11) 0.1957(4) 0.60670(17) 0.0487(9) Uani 1 1 d . U . . .
H62 H 0.3124 0.2816 0.5870 0.058 Uiso 1 1 calc R U . . .
C13 C 0.32688(11) 0.3676(4) 0.47555(16) 0.0392(7) Uani 1 1 d . U . . .
C23 C 0.28486(12) 0.4241(4) 0.42944(18) 0.0538(9) Uani 1 1 d . U . . .
H23 H 0.2616 0.3641 0.3974 0.065 Uiso 1 1 calc R U . . .
C33 C 0.27712(14) 0.5697(4) 0.4305(2) 0.0662(11) Uani 1 1 d . U . . .
H33 H 0.2487 0.6064 0.3990 0.079 Uiso 1 1 calc R U . . .
C43 C 0.31021(14) 0.6584(4) 0.4766(2) 0.0687(11) Uani 1 1 d . U . . .
H43 H 0.3048 0.7561 0.4765 0.082 Uiso 1 1 calc R U . . .
C53 C 0.35147(15) 0.6047(4) 0.5230(2) 0.0735(11) Uani 1 1 d . U . . .
H53 H 0.3742 0.6655 0.5558 0.088 Uiso 1 1 calc R U . . .
C63 C 0.36016(13) 0.4606(4) 0.52197(19) 0.0609(10) Uani 1 1 d . U . . .
H63 H 0.3889 0.4259 0.5532 0.073 Uiso 1 1 calc R U . . .
C14 C 0.37820(14) -0.1878(4) 0.3946(2) 0.0624(10) Uani 1 1 d . U . . .
H14 H 0.3496 -0.1562 0.3600 0.075 Uiso 1 1 calc R U . . .
C24 C 0.39024(16) -0.3288(5) 0.3894(2) 0.0739(11) Uani 1 1 d . U . . .
H24 H 0.3700 -0.3897 0.3520 0.089 Uiso 1 1 calc R U . . .
C34 C 0.43179(15) -0.3751(5) 0.4398(2) 0.0764(11) Uani 1 1 d . U . . .
H34 H 0.4404 -0.4689 0.4380 0.092 Uiso 1 1 calc R U . . .
C44 C 0.46082(14) -0.2829(4) 0.4931(2) 0.0671(11) Uani 1 1 d . U . . .
H44 H 0.4898 -0.3125 0.5272 0.081 Uiso 1 1 calc R U . . .
C54 C 0.44715(12) -0.1448(4) 0.49670(19) 0.0501(8) Uani 1 1 d . U . . .
C64 C 0.47663(12) -0.0426(4) 0.55313(19) 0.0524(9) Uani 1 1 d . U . . .
H64 H 0.5058 -0.0684 0.5880 0.063 Uiso 1 1 calc R U . . .
C15 C 0.48936(11) 0.1852(4) 0.61011(18) 0.0473(8) Uani 1 1 d . U . . .
C25 C 0.52585(12) 0.1492(5) 0.68027(19) 0.0692(11) Uani 1 1 d . U . . .
H25 H 0.5337 0.0538 0.6931 0.083 Uiso 1 1 calc R U . . .
C35 C 0.54983(13) 0.2567(5) 0.7298(2) 0.0749(11) Uani 1 1 d . U . . .
H35 H 0.5738 0.2318 0.7766 0.090 Uiso 1 1 calc R U . . .
C45 C 0.54006(13) 0.3986(5) 0.71357(19) 0.0630(10) Uani 1 1 d . U . . .
C55 C 0.50309(13) 0.4316(4) 0.64458(19) 0.0649(11) Uani 1 1 d . U . . .
H55 H 0.4949 0.5270 0.6323 0.078 Uiso 1 1 calc R U . . .
C65 C 0.47829(12) 0.3262(4) 0.59399(19) 0.0548(9) Uani 1 1 d . U . . .
H65 H 0.4536 0.3513 0.5481 0.066 Uiso 1 1 calc R U . . .
C75 C 0.56841(15) 0.5146(5) 0.7674(2) 0.0987(16) Uani 1 1 d . U . . .
H75A H 0.5541 0.5493 0.7950 0.148 Uiso 1 1 calc R U . . .
H75B H 0.5718 0.5920 0.7393 0.148 Uiso 1 1 calc R U . . .
H75C H 0.5974 0.4765 0.8021 0.148 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 2.098(3) . ?
Cu1 N2 2.101(3) . ?
Cu1 P1 2.1850(9) . ?
Cu1 Br2 2.4230(5) . ?
P1 C13 1.824(3) . ?
P1 C11 1.825(3) . ?
P1 C12 1.836(3) . ?
N1 C14 1.331(4) . ?
N1 C54 1.342(4) . ?
N2 C64 1.271(4) . ?
N2 C15 1.424(4) . ?
C11 C61 1.374(4) . ?
C11 C21 1.406(4) . ?
C21 C31 1.383(5) . ?
C21 H21 0.9300 . ?
C31 C41 1.360(5) . ?
C31 H31 0.9300 . ?
C41 C51 1.360(5) . ?
C41 H41 0.9300 . ?
C51 C61 1.382(4) . ?
C51 H51 0.9300 . ?
C61 H61 0.9300 . ?
C12 C22 1.380(4) . ?
C12 C62 1.387(4) . ?
C22 C32 1.376(4) . ?
C22 H22 0.9300 . ?
C32 C42 1.362(5) . ?
C32 H32 0.9300 . ?
C42 C52 1.362(5) . ?
C42 H42 0.9300 . ?
C52 C62 1.391(4) . ?
C52 H52 0.9300 . ?
C62 H62 0.9300 . ?
C13 C63 1.374(4) . ?
C13 C23 1.380(4) . ?
C23 C33 1.387(5) . ?
C23 H23 0.9300 . ?
C33 C43 1.344(5) . ?
C33 H33 0.9300 . ?
C43 C53 1.353(5) . ?
C43 H43 0.9300 . ?
C53 C63 1.380(5) . ?
C53 H53 0.9300 . ?
C63 H63 0.9300 . ?
C14 C24 1.398(5) . ?
C14 H14 0.9300 . ?
C24 C34 1.353(5) . ?
C24 H24 0.9300 . ?
C34 C44 1.359(5) . ?
C34 H34 0.9300 . ?
C44 C54 1.385(5) . ?
C44 H44 0.9300 . ?
C54 C64 1.452(5) . ?
C64 H64 0.9300 . ?
C15 C65 1.364(5) . ?
C15 C25 1.400(4) . ?
C25 C35 1.373(5) . ?
C25 H25 0.9300 . ?
C35 C45 1.367(5) . ?
C35 H35 0.9300 . ?
C45 C55 1.387(5) . ?
C45 C75 1.506(5) . ?
C55 C65 1.375(5) . ?
C55 H55 0.9300 . ?
C65 H65 0.9300 . ?
C75 H75A 0.9600 . ?
C75 H75B 0.9600 . ?
C75 H75C 0.9600 . ?

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 79.11(11) . . ?
N1 Cu1 P1 117.06(8) . . ?
N2 Cu1 P1 122.46(7) . . ?
N1 Cu1 Br2 106.10(7) . . ?
N2 Cu1 Br2 108.51(7) . . ?
P1 Cu1 Br2 116.97(3) . . ?
C13 P1 C11 104.65(15) . . ?
C13 P1 C12 102.86(14) . . ?
C11 P1 C12 103.51(14) . . ?
C13 P1 Cu1 118.01(11) . . ?
C11 P1 Cu1 111.11(10) . . ?
C12 P1 Cu1 115.17(11) . . ?
C14 N1 C54 117.8(3) . . ?
C14 N1 Cu1 130.1(3) . . ?
C54 N1 Cu1 112.1(2) . . ?
C64 N2 C15 121.8(3) . . ?
C64 N2 Cu1 112.7(3) . . ?
C15 N2 Cu1 125.4(2) . . ?
C61 C11 C21 117.8(3) . . ?
C61 C11 P1 124.7(2) . . ?
C21 C11 P1 117.5(3) . . ?
C31 C21 C11 119.2(4) . . ?
C31 C21 H21 120.4 . . ?
C11 C21 H21 120.4 . . ?
C41 C31 C21 121.7(4) . . ?
C41 C31 H31 119.2 . . ?
C21 C31 H31 119.2 . . ?
C51 C41 C31 119.4(4) . . ?
C51 C41 H41 120.3 . . ?
C31 C41 H41 120.3 . . ?
C41 C51 C61 120.2(4) . . ?
C41 C51 H51 119.9 . . ?
C61 C51 H51 119.9 . . ?
C11 C61 C51 121.6(3) . . ?
C11 C61 H61 119.2 . . ?
C51 C61 H61 119.2 . . ?
C22 C12 C62 118.9(3) . . ?
C22 C12 P1 117.9(2) . . ?
C62 C12 P1 123.2(3) . . ?
C32 C22 C12 121.0(3) . . ?
C32 C22 H22 119.5 . . ?
C12 C22 H22 119.5 . . ?
C42 C32 C22 119.7(4) . . ?
C42 C32 H32 120.1 . . ?
C22 C32 H32 120.1 . . ?
C52 C42 C32 120.6(3) . . ?
C52 C42 H42 119.7 . . ?
C32 C42 H42 119.7 . . ?
C42 C52 C62 120.4(3) . . ?
C42 C52 H52 119.8 . . ?
C62 C52 H52 119.8 . . ?
C12 C62 C52 119.4(3) . . ?
C12 C62 H62 120.3 . . ?
C52 C62 H62 120.3 . . ?
C63 C13 C23 117.5(3) . . ?
C63 C13 P1 118.1(3) . . ?
C23 C13 P1 124.4(3) . . ?
C13 C23 C33 120.5(4) . . ?
C13 C23 H23 119.8 . . ?
C33 C23 H23 119.8 . . ?
C43 C33 C23 120.9(4) . . ?
C43 C33 H33 119.6 . . ?
C23 C33 H33 119.6 . . ?
C33 C43 C53 119.5(4) . . ?
C33 C43 H43 120.2 . . ?
C53 C43 H43 120.2 . . ?
C43 C53 C63 120.7(4) . . ?
C43 C53 H53 119.7 . . ?
C63 C53 H53 119.7 . . ?
C13 C63 C53 120.9(4) . . ?
C13 C63 H63 119.5 . . ?
C53 C63 H63 119.5 . . ?
N1 C14 C24 122.5(4) . . ?
N1 C14 H14 118.7 . . ?
C24 C14 H14 118.7 . . ?
C34 C24 C14 118.9(5) . . ?
C34 C24 H24 120.6 . . ?
C14 C24 H24 120.6 . . ?
C24 C34 C44 119.2(4) . . ?
C24 C34 H34 120.4 . . ?
C44 C34 H34 120.4 . . ?
C34 C44 C54 119.8(4) . . ?
C34 C44 H44 120.1 . . ?
C54 C44 H44 120.1 . . ?
N1 C54 C44 121.8(4) . . ?
N1 C54 C64 116.1(3) . . ?
C44 C54 C64 122.1(4) . . ?
N2 C64 C54 119.6(3) . . ?
N2 C64 H64 120.2 . . ?
C54 C64 H64 120.2 . . ?
C65 C15 C25 118.7(4) . . ?
C65 C15 N2 117.6(3) . . ?
C25 C15 N2 123.7(4) . . ?
C35 C25 C15 119.0(4) . . ?
C35 C25 H25 120.5 . . ?
C15 C25 H25 120.5 . . ?
C45 C35 C25 123.0(4) . . ?
C45 C35 H35 118.5 . . ?
C25 C35 H35 118.5 . . ?
C35 C45 C55 117.0(4) . . ?
C35 C45 C75 121.8(4) . . ?
C55 C45 C75 121.2(4) . . ?
C65 C55 C45 121.3(4) . . ?
C65 C55 H55 119.4 . . ?
C45 C55 H55 119.4 . . ?
C15 C65 C55 120.9(3) . . ?
C15 C65 H65 119.5 . . ?
C55 C65 H65 119.5 . . ?
C45 C75 H75A 109.5 . . ?
C45 C75 H75B 109.5 . . ?
H75A C75 H75B 109.5 . . ?
C45 C75 H75C 109.5 . . ?
H75A C75 H75C 109.5 . . ?
H75B C75 H75C 109.5 . . ?

_refine_diff_density_max         0.677
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.053

_shelxl_version_number           2014/6

