# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_URMIA20
_database_code_depnum_ccdc_archive 'CCDC 1841592'
_audit_update_record             
;
2018-05-06 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;
_audit_creation_date             2017-12-20
_audit_creation_method           'by CrystalStructure 4.2'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C10 H21 Cl2 N2 O2 Zn'
_chemical_formula_moiety         'C10 H21 Cl2 N2 O2 Zn'
_chemical_formula_weight         337.57
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.3713(8)
_cell_length_b                   12.4965(9)
_cell_length_c                   11.9806(9)
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.277(8)
_cell_angle_gamma                90.0000
_cell_volume                     1548.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    40
_cell_measurement_theta_min      1.60
_cell_measurement_theta_max      25.40
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700.00
_exptl_absorpt_coefficient_mu    1.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.425
_exptl_absorpt_correction_T_max  0.908

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.653
_diffrn_reflns_number            13000
_diffrn_reflns_av_R_equivalents  0.1867
_diffrn_reflns_theta_max         25.384
_diffrn_reflns_theta_min         2.359
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2830
_reflns_number_gt                1576
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1247
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2830
_refine_ls_number_parameters     188
_refine_ls_goodness_of_fit_ref   0.841
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0592P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.84
_refine_diff_density_min         -0.61
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Zn Zn 0.2839 1.4301
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Zn1 Zn 0.46788(7) 0.55597(5) 0.74385(5) 0.0419(2) Uani 1 1 d . . . . .
Cl1 Cl 0.33042(15) 0.54350(12) 0.87907(11) 0.0485(4) Uani 1 1 d . . . . .
Cl2 Cl 0.50947(18) 0.40602(11) 0.64162(11) 0.0555(5) Uani 1 1 d . . . . .
O2A O 0.1985(9) 0.4541(7) 0.5126(7) 0.081(3) Uani 0.6 1 d . . P A 1
O2B O 0.1830(12) 0.5616(12) 0.4113(10) 0.085(4) Uani 0.4 1 d . . P B 2
O10 O 0.6465(4) 0.5173(3) 0.8630(3) 0.0500(11) Uani 1 1 d . . . . .
N1 N 0.3588(5) 0.6304(4) 0.6050(4) 0.0475(13) Uani 1 1 d D . . . .
H1 H 0.383(5) 0.590(4) 0.542(3) 0.048(16) Uiso 1 1 d D . . . .
N5 N 0.5850(5) 0.6889(4) 0.7329(3) 0.0398(11) Uani 1 1 d D . . . .
H5 H 0.566(4) 0.746(3) 0.784(3) 0.033(14) Uiso 1 1 d D . . . .
C1 C 0.2157(7) 0.6252(7) 0.5966(6) 0.071(2) Uani 1 1 d . . . . .
H1A H 0.1849 0.6656 0.6606 0.07(5) Uiso 0.6 1 calc R . P C 1
H1B H 0.1839 0.6635 0.5276 0.04(4) Uiso 0.6 1 calc R . P C 1
H1C H 0.1897 0.5556 0.6275 0.00(3) Uiso 0.4 1 calc R . P D 2
H1D H 0.1831 0.6820 0.6448 0.04(5) Uiso 0.4 1 calc R . P D 2
C2A C 0.1556(12) 0.5225(9) 0.5948(9) 0.058(3) Uani 0.6 1 d . . P A 1
H2A H 0.1729 0.4885 0.6690 0.14(6) Uiso 0.6 1 calc R . P A 1
H2B H 0.0609 0.5319 0.5817 0.04(3) Uiso 0.6 1 calc R . P A 1
C2B C 0.156(2) 0.636(2) 0.4920(17) 0.072(6) Uani 0.4 1 d . . P B 2
H2C H 0.1775 0.7078 0.4637 0.11(8) Uiso 0.4 1 calc R . P B 2
H2D H 0.0613 0.6349 0.4992 0.25(16) Uiso 0.4 1 calc R . P B 2
C3 C 0.4088(7) 0.7396(5) 0.5977(4) 0.0519(17) Uani 1 1 d . . . . .
H3A H 0.3689 0.7859 0.6526 0.062 Uiso 1 1 calc R U . . .
H3B H 0.3862 0.7688 0.5219 0.062 Uiso 1 1 calc R U . . .
C4 C 0.5508(7) 0.7392(5) 0.6208(4) 0.0517(16) Uani 1 1 d . . . . .
H4A H 0.5841 0.8134 0.6203 0.062 Uiso 1 1 calc R U . . .
H4B H 0.5913 0.6983 0.5618 0.062 Uiso 1 1 calc R U . . .
C5 C 0.7216(6) 0.6618(5) 0.7558(5) 0.0486(15) Uani 1 1 d . . . . .
H5A H 0.7461 0.6106 0.6969 0.058 Uiso 1 1 calc R U . . .
C6 C 0.8143(7) 0.7564(6) 0.7569(6) 0.070(2) Uani 1 1 d . . . . .
H6A H 0.7887 0.8101 0.8119 0.084 Uiso 1 1 calc R U . . .
H6B H 0.8086 0.7905 0.6821 0.084 Uiso 1 1 calc R U . . .
C7 C 0.9535(8) 0.7212(8) 0.7873(9) 0.115(4) Uani 1 1 d . . . . .
H7A H 0.9823 0.6738 0.7279 0.138 Uiso 1 1 calc R U . . .
H7B H 1.0104 0.7849 0.7918 0.138 Uiso 1 1 calc R U . . .
C8 C 0.9658(8) 0.6629(9) 0.8975(10) 0.123(4) Uani 1 1 d . . . . .
H8A H 0.9449 0.7122 0.9582 0.147 Uiso 1 1 calc R U . . .
H8B H 1.0560 0.6381 0.9131 0.147 Uiso 1 1 calc R U . . .
C9 C 0.8744(7) 0.5670(7) 0.8950(8) 0.094(3) Uani 1 1 d . . . . .
H9A H 0.8984 0.5153 0.8374 0.113 Uiso 1 1 calc R U . . .
H9B H 0.8820 0.5304 0.9685 0.113 Uiso 1 1 calc R U . . .
C10 C 0.7361(6) 0.6043(5) 0.8687(5) 0.0487(15) Uani 1 1 d . . . . .
H10A H 0.7125 0.6549 0.9285 0.058 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Zn1 N5 2.068(5) . ?
Zn1 N1 2.152(5) . ?
Zn1 Cl1 2.2418(15) . ?
Zn1 Cl2 2.2970(15) . ?
Zn1 O10 2.304(4) . ?
O2A C2A 1.402(13) . ?
O2B C2B 1.39(2) . ?
O10 C10 1.428(7) . ?
N1 C3 1.464(7) . ?
N1 C1 1.482(8) . ?
N1 H1 0.958(19) . ?
N5 C5 1.462(8) . ?
N5 C4 1.501(7) . ?
N5 H5 0.971(19) . ?
C1 C2B 1.36(2) . ?
C1 C2A 1.426(14) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C2A H2A 0.9900 . ?
C2A H2B 0.9900 . ?
C2B H2C 0.9900 . ?
C2B H2D 0.9900 . ?
C3 C4 1.479(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.522(9) . ?
C5 C10 1.530(7) . ?
C5 H5A 1.0000 . ?
C6 C7 1.527(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.504(11) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.527(12) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.519(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 1.0000 . ?

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
N5 Zn1 N1 83.16(18) . . ?
N5 Zn1 Cl1 120.67(13) . . ?
N1 Zn1 Cl1 105.24(14) . . ?
N5 Zn1 Cl2 119.12(13) . . ?
N1 Zn1 Cl2 92.83(13) . . ?
Cl1 Zn1 Cl2 118.91(6) . . ?
N5 Zn1 O10 76.04(16) . . ?
N1 Zn1 O10 157.13(17) . . ?
Cl1 Zn1 O10 93.61(11) . . ?
Cl2 Zn1 O10 89.13(11) . . ?
C10 O10 Zn1 111.1(3) . . ?
C3 N1 C1 113.2(5) . . ?
C3 N1 Zn1 106.3(4) . . ?
C1 N1 Zn1 119.9(4) . . ?
C3 N1 H1 109(3) . . ?
C1 N1 H1 104(3) . . ?
Zn1 N1 H1 103(3) . . ?
C5 N5 C4 115.2(5) . . ?
C5 N5 Zn1 111.6(3) . . ?
C4 N5 Zn1 107.0(3) . . ?
C5 N5 H5 107(3) . . ?
C4 N5 H5 102(3) . . ?
Zn1 N5 H5 113(3) . . ?
C2B C1 N1 116.3(11) . . ?
C2A C1 N1 118.4(8) . . ?
C2A C1 H1A 107.7 . . ?
N1 C1 H1A 107.7 . . ?
C2A C1 H1B 107.7 . . ?
N1 C1 H1B 107.7 . . ?
H1A C1 H1B 107.1 . . ?
C2B C1 H1C 108.2 . . ?
N1 C1 H1C 108.2 . . ?
C2B C1 H1D 108.2 . . ?
N1 C1 H1D 108.2 . . ?
H1C C1 H1D 107.4 . . ?
O2A C2A C1 113.5(9) . . ?
O2A C2A H2A 108.9 . . ?
C1 C2A H2A 108.9 . . ?
O2A C2A H2B 108.9 . . ?
C1 C2A H2B 108.9 . . ?
H2A C2A H2B 107.7 . . ?
C1 C2B O2B 118.2(14) . . ?
C1 C2B H2C 107.8 . . ?
O2B C2B H2C 107.8 . . ?
C1 C2B H2D 107.8 . . ?
O2B C2B H2D 107.8 . . ?
H2C C2B H2D 107.1 . . ?
N1 C3 C4 109.7(5) . . ?
N1 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
N1 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C3 C4 N5 109.6(5) . . ?
C3 C4 H4A 109.8 . . ?
N5 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
N5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
N5 C5 C6 115.1(5) . . ?
N5 C5 C10 107.7(4) . . ?
C6 C5 C10 109.7(5) . . ?
N5 C5 H5A 108.0 . . ?
C6 C5 H5A 108.0 . . ?
C10 C5 H5A 108.0 . . ?
C5 C6 C7 111.4(6) . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 111.4(7) . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C9 110.6(9) . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 109.7(7) . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
O10 C10 C9 112.2(5) . . ?
O10 C10 C5 107.2(5) . . ?
C9 C10 C5 110.9(5) . . ?
O10 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C5 C10 H10A 108.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C2B 77.2(14) . . . . ?
Zn1 N1 C1 C2B -156.0(13) . . . . ?
C3 N1 C1 C2A 175.7(7) . . . . ?
Zn1 N1 C1 C2A -57.4(8) . . . . ?
N1 C1 C2A O2A -53.2(12) . . . . ?
N1 C1 C2B O2B 61(2) . . . . ?
C1 N1 C3 C4 173.0(5) . . . . ?
Zn1 N1 C3 C4 39.2(5) . . . . ?
N1 C3 C4 N5 -56.1(6) . . . . ?
C5 N5 C4 C3 167.1(5) . . . . ?
Zn1 N5 C4 C3 42.5(5) . . . . ?
C4 N5 C5 C6 61.5(7) . . . . ?
Zn1 N5 C5 C6 -176.2(4) . . . . ?
C4 N5 C5 C10 -175.8(5) . . . . ?
Zn1 N5 C5 C10 -53.5(5) . . . . ?
N5 C5 C6 C7 177.1(6) . . . . ?
C10 C5 C6 C7 55.4(8) . . . . ?
C5 C6 C7 C8 -55.6(11) . . . . ?
C6 C7 C8 C9 56.5(12) . . . . ?
C7 C8 C9 C10 -58.0(11) . . . . ?
Zn1 O10 C10 C9 -151.7(5) . . . . ?
Zn1 O10 C10 C5 -29.7(5) . . . . ?
C8 C9 C10 O10 178.8(7) . . . . ?
C8 C9 C10 C5 59.0(10) . . . . ?
N5 C5 C10 O10 53.6(6) . . . . ?
C6 C5 C10 O10 179.6(5) . . . . ?
N5 C5 C10 C9 176.3(6) . . . . ?
C6 C5 C10 C9 -57.7(8) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O2A . . . 2.928(10) 0.96(4) 2.56(5) 103(4) no
N1 H1 O2B . . . 2.970(13) 0.96(4) 2.53(5) 108(4) no
N5 H5 Cl2 . . 2_656 3.287(5) 0.971 2.348 162.5 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_URMIA19
_database_code_depnum_ccdc_archive 'CCDC 1841593'
_audit_update_record             
;
2018-05-06 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;
_audit_creation_date             2017-12-20
_audit_creation_method           'by CrystalStructure 4.2'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C10 H22 Cl2 Cu N2 O2'
_chemical_formula_moiety         'C10 H22 Cl2 Cu N2 O2'
_chemical_formula_weight         336.75
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,+Z
7 +X,-1/2-Y,-1/2+Z
8 -1/2+X,+Y,-1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.63584(15)
_cell_length_b                   11.8221(3)
_cell_length_c                   34.9929(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2745.18(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    28882
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      28.29
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1400.00
_exptl_absorpt_coefficient_mu    1.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.148
_exptl_absorpt_correction_T_max  0.906

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            57562
_diffrn_reflns_av_R_equivalents  0.0841
_diffrn_reflns_theta_max         28.399
_diffrn_reflns_theta_min         2.328
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       46
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3242
_reflns_number_gt                2939
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0720
_refine_ls_wR_factor_ref         0.1818
_refine_ls_wR_factor_gt          0.1792
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3242
_refine_ls_number_parameters     170
_refine_ls_goodness_of_fit_ref   1.268
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0387P)²+41.9438P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.003
_refine_diff_density_max         3.51
_refine_diff_density_min         -0.92
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.62008(10) 0.66157(6) 0.66656(2) 0.0086(2) Uani 1 1 d . . . . .
Cl1 Cl 0.4297(2) 0.75222(12) 0.71020(4) 0.0114(3) Uani 1 1 d . . . . .
Cl2 Cl 0.3903(2) 0.35517(12) 0.60170(4) 0.0131(3) Uani 1 1 d . . . . .
O2 O 0.4780(6) 0.4902(3) 0.67216(12) 0.0116(8) Uani 1 1 d D . . . .
O10 O 0.4578(7) 0.6988(4) 0.61962(12) 0.0141(9) Uani 1 1 d D . . . .
N1 N 0.8168(8) 0.5921(4) 0.70416(14) 0.0114(10) Uani 1 1 d D . . . .
N5 N 0.8364(7) 0.6333(4) 0.62751(14) 0.0099(9) Uani 1 1 d D . . . .
C1 C 0.7120(9) 0.4966(5) 0.72347(16) 0.0118(11) Uani 1 1 d . . . . .
H1A H 0.6135 0.5274 0.7420 0.014 Uiso 1 1 calc R U . . .
H1B H 0.8121 0.4515 0.7379 0.014 Uiso 1 1 calc R U . . .
C2 C 0.6038(9) 0.4202(5) 0.69570(17) 0.0119(11) Uani 1 1 d . . . . .
H2A H 0.7023 0.3788 0.6797 0.014 Uiso 1 1 calc R U . . .
H2B H 0.5207 0.3643 0.7097 0.014 Uiso 1 1 calc R U . . .
C3 C 1.0066(9) 0.5611(5) 0.68388(16) 0.0129(11) Uani 1 1 d . . . . .
H3A H 1.0647 0.4921 0.6955 0.016 Uiso 1 1 calc R U . . .
H3B H 1.1059 0.6231 0.6866 0.016 Uiso 1 1 calc R U . . .
C4 C 0.9651(9) 0.5401(5) 0.64196(17) 0.0129(12) Uani 1 1 d . . . . .
H4A H 1.0934 0.5377 0.6275 0.015 Uiso 1 1 calc R U . . .
H4B H 0.8956 0.4667 0.6386 0.015 Uiso 1 1 calc R U . . .
C5 C 0.7347(9) 0.6080(5) 0.59065(16) 0.0104(11) Uani 1 1 d . . . . .
H5A H 0.6644 0.5336 0.5932 0.013 Uiso 1 1 calc R U . . .
C6 C 0.8766(9) 0.6011(5) 0.55645(17) 0.0120(11) Uani 1 1 d . . . . .
H6A H 0.9720 0.5376 0.5601 0.014 Uiso 1 1 calc R U . . .
H6B H 0.9556 0.6719 0.5545 0.014 Uiso 1 1 calc R U . . .
C7 C 0.7564(10) 0.5830(6) 0.51965(17) 0.0165(12) Uani 1 1 d . . . . .
H7A H 0.6939 0.5070 0.5202 0.020 Uiso 1 1 calc R U . . .
H7B H 0.8490 0.5861 0.4975 0.020 Uiso 1 1 calc R U . . .
C8 C 0.5917(9) 0.6724(5) 0.51477(17) 0.0149(12) Uani 1 1 d . . . . .
H8A H 0.5122 0.6554 0.4915 0.018 Uiso 1 1 calc R U . . .
H8B H 0.6547 0.7476 0.5114 0.018 Uiso 1 1 calc R U . . .
C9 C 0.4515(9) 0.6751(6) 0.54951(17) 0.0151(12) Uani 1 1 d . . . . .
H9A H 0.3481 0.7346 0.5461 0.018 Uiso 1 1 calc R U . . .
H9B H 0.3821 0.6014 0.5522 0.018 Uiso 1 1 calc R U . . .
C10 C 0.5752(9) 0.6993(5) 0.58493(16) 0.0111(11) Uani 1 1 d . . . . .
H10A H 0.6429 0.7744 0.5821 0.013 Uiso 1 1 calc R U . . .
H1 H 0.847(12) 0.648(5) 0.7232(17) 0.02(2) Uiso 1 1 d D . . . .
H2 H 0.478(15) 0.447(7) 0.6484(15) 0.04(3) Uiso 1 1 d D . . . .
H5 H 0.901(9) 0.708(3) 0.6230(18) 0.000(14) Uiso 1 1 d D . . . .
H10 H 0.399(13) 0.774(4) 0.619(3) 0.04(3) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 N5 2.010(5) . ?
Cu1 O10 2.013(4) . ?
Cu1 N1 2.028(5) . ?
Cu1 O2 2.243(4) . ?
Cu1 Cl1 2.2533(15) . ?
O2 C2 1.435(7) . ?
O2 H2 0.98(2) . ?
O10 C10 1.443(7) . ?
O10 H10 0.97(2) . ?
N1 C1 1.488(7) . ?
N1 C3 1.491(8) . ?
N1 H1 0.96(2) . ?
N5 C4 1.483(7) . ?
N5 C5 1.486(7) . ?
N5 H5 0.99(2) . ?
C1 C2 1.509(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.513(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.524(8) . ?
C5 C6 1.525(8) . ?
C5 H5A 1.0000 . ?
C6 C7 1.530(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.529(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.531(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.514(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 1.0000 . ?

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
N5 Cu1 O10 82.16(19) . . ?
N5 Cu1 N1 85.1(2) . . ?
O10 Cu1 N1 164.30(19) . . ?
N5 Cu1 O2 102.09(18) . . ?
O10 Cu1 O2 92.52(17) . . ?
N1 Cu1 O2 81.26(18) . . ?
N5 Cu1 Cl1 160.11(15) . . ?
O10 Cu1 Cl1 98.57(13) . . ?
N1 Cu1 Cl1 96.55(15) . . ?
O2 Cu1 Cl1 97.74(12) . . ?
C2 O2 Cu1 109.0(3) . . ?
C2 O2 H2 101(6) . . ?
Cu1 O2 H2 114(6) . . ?
C10 O10 Cu1 113.5(3) . . ?
C10 O10 H10 101(6) . . ?
Cu1 O10 H10 116(6) . . ?
C1 N1 C3 115.1(5) . . ?
C1 N1 Cu1 107.5(4) . . ?
C3 N1 Cu1 109.5(4) . . ?
C1 N1 H1 108(5) . . ?
C3 N1 H1 109(5) . . ?
Cu1 N1 H1 108(5) . . ?
C4 N5 C5 114.1(5) . . ?
C4 N5 Cu1 107.6(4) . . ?
C5 N5 Cu1 107.4(3) . . ?
C4 N5 H5 118(4) . . ?
C5 N5 H5 104(4) . . ?
Cu1 N5 H5 106(4) . . ?
N1 C1 C2 112.6(5) . . ?
N1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
O2 C2 C1 107.6(5) . . ?
O2 C2 H2A 110.2 . . ?
C1 C2 H2A 110.2 . . ?
O2 C2 H2B 110.2 . . ?
C1 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
N1 C3 C4 110.4(5) . . ?
N1 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
N5 C4 C3 108.3(5) . . ?
N5 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
N5 C4 H4B 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
N5 C5 C10 106.7(5) . . ?
N5 C5 C6 114.3(5) . . ?
C10 C5 C6 111.3(5) . . ?
N5 C5 H5A 108.1 . . ?
C10 C5 H5A 108.1 . . ?
C6 C5 H5A 108.1 . . ?
C5 C6 C7 110.2(5) . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 C8 111.7(5) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 111.1(5) . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 108.9(5) . . ?
C10 C9 H9A 109.9 . . ?
C8 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
O10 C10 C9 113.3(5) . . ?
O10 C10 C5 105.2(5) . . ?
C9 C10 C5 110.5(5) . . ?
O10 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C5 C10 H10A 109.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C2 -75.2(6) . . . . ?
Cu1 N1 C1 C2 47.2(5) . . . . ?
Cu1 O2 C2 C1 29.7(5) . . . . ?
N1 C1 C2 O2 -52.0(6) . . . . ?
C1 N1 C3 C4 95.6(6) . . . . ?
Cu1 N1 C3 C4 -25.7(6) . . . . ?
C5 N5 C4 C3 -163.0(5) . . . . ?
Cu1 N5 C4 C3 -43.9(5) . . . . ?
N1 C3 C4 N5 46.2(6) . . . . ?
C4 N5 C5 C10 167.3(5) . . . . ?
Cu1 N5 C5 C10 48.1(5) . . . . ?
C4 N5 C5 C6 -69.1(6) . . . . ?
Cu1 N5 C5 C6 171.6(4) . . . . ?
N5 C5 C6 C7 -176.1(5) . . . . ?
C10 C5 C6 C7 -55.1(7) . . . . ?
C5 C6 C7 C8 53.5(7) . . . . ?
C6 C7 C8 C9 -55.8(7) . . . . ?
C7 C8 C9 C10 58.2(7) . . . . ?
Cu1 O10 C10 C9 154.3(4) . . . . ?
Cu1 O10 C10 C5 33.5(5) . . . . ?
C8 C9 C10 O10 -177.5(5) . . . . ?
C8 C9 C10 C5 -59.8(7) . . . . ?
N5 C5 C10 O10 -52.8(6) . . . . ?
C6 C5 C10 O10 -178.1(5) . . . . ?
N5 C5 C10 C9 -175.4(5) . . . . ?
C6 C5 C10 C9 59.3(6) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 Cl2 . . . 2.994(4) 0.98(6) 2.04(7) 163(9) no
O10 H10 Cl2 . . 6_665 3.024(5) 0.97(5) 2.23(8) 138(6) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_URMIA18
_database_code_depnum_ccdc_archive 'CCDC 1841594'
_audit_update_record             
;
2018-05-06 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;
_audit_creation_date             2017-12-20
_audit_creation_method           'by CrystalStructure 4.2'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C10 H22 Br2 Cu N2 O2'
_chemical_formula_moiety         'C10 H22 Br2 Cu N2 O2'
_chemical_formula_weight         425.65
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,+Z
7 +X,-1/2-Y,-1/2+Z
8 -1/2+X,+Y,-1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.68836(15)
_cell_length_b                   12.3506(3)
_cell_length_c                   35.1567(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2904.13(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    42764
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.55
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1688.00
_exptl_absorpt_coefficient_mu    7.017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.095
_exptl_absorpt_correction_T_max  0.656

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            61924
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_theta_max         28.383
_diffrn_reflns_theta_min         2.317
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       46
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3452
_reflns_number_gt                3179
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0206
_refine_ls_wR_factor_ref         0.0541
_refine_ls_wR_factor_gt          0.0532
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3452
_refine_ls_number_parameters     170
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0263P)²+3.5167P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.002
_refine_diff_density_max         0.68
_refine_diff_density_min         -0.46
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.57330(3) 0.76624(2) 0.28999(2) 0.01473(6) Uani 1 1 d . . . . .
Br2 Br 0.61007(3) 0.36329(2) 0.40025(2) 0.01683(6) Uani 1 1 d . . . . .
Cu1 Cu 0.37720(3) 0.66610(2) 0.33494(2) 0.01208(7) Uani 1 1 d . . . . .
O2 O 0.5205(2) 0.50378(11) 0.32725(4) 0.0161(3) Uani 1 1 d D . . . .
O10 O 0.5409(2) 0.69738(13) 0.38139(4) 0.0175(3) Uani 1 1 d D . . . .
N1 N 0.1840(2) 0.60261(14) 0.29685(4) 0.0131(3) Uani 1 1 d D . . . .
N5 N 0.1636(3) 0.63699(13) 0.37382(5) 0.0136(3) Uani 1 1 d D . . . .
C1 C 0.2862(3) 0.51220(16) 0.27686(5) 0.0164(4) Uani 1 1 d . . . . .
H1A H 0.3834 0.5424 0.2585 0.020 Uiso 1 1 calc R U . . .
H1B H 0.1860 0.4701 0.2624 0.020 Uiso 1 1 calc R U . . .
C2 C 0.3944(3) 0.43744(17) 0.30391(6) 0.0157(4) Uani 1 1 d . . . . .
H2A H 0.2973 0.3974 0.3198 0.019 Uiso 1 1 calc R U . . .
H2B H 0.4757 0.3844 0.2896 0.019 Uiso 1 1 calc R U . . .
C3 C -0.0058(3) 0.57281(17) 0.31693(5) 0.0157(4) Uani 1 1 d . . . . .
H3A H -0.0649 0.5079 0.3048 0.019 Uiso 1 1 calc R U . . .
H3B H -0.1030 0.6329 0.3147 0.019 Uiso 1 1 calc R U . . .
C4 C 0.0345(3) 0.54971(17) 0.35875(6) 0.0169(4) Uani 1 1 d . . . . .
H4A H -0.0930 0.5473 0.3730 0.020 Uiso 1 1 calc R U . . .
H4B H 0.1019 0.4788 0.3616 0.020 Uiso 1 1 calc R U . . .
C5 C 0.2638(3) 0.61146(16) 0.41039(5) 0.0139(4) Uani 1 1 d . . . . .
H5A H 0.3318 0.5398 0.4076 0.017 Uiso 1 1 calc R U . . .
C6 C 0.1238(3) 0.60466(18) 0.44460(6) 0.0181(4) Uani 1 1 d . . . . .
H6A H 0.0264 0.5453 0.4407 0.022 Uiso 1 1 calc R U . . .
H6B H 0.0486 0.6733 0.4472 0.022 Uiso 1 1 calc R U . . .
C7 C 0.2448(3) 0.58372(19) 0.48097(6) 0.0223(4) Uani 1 1 d . . . . .
H7A H 0.1543 0.5862 0.5032 0.027 Uiso 1 1 calc R U . . .
H7B H 0.3045 0.5105 0.4798 0.027 Uiso 1 1 calc R U . . .
C8 C 0.4106(3) 0.6677(2) 0.48594(6) 0.0214(5) Uani 1 1 d . . . . .
H8A H 0.4902 0.6497 0.5088 0.026 Uiso 1 1 calc R U . . .
H8B H 0.3501 0.7400 0.4899 0.026 Uiso 1 1 calc R U . . .
C9 C 0.5485(3) 0.67125(19) 0.45113(6) 0.0196(4) Uani 1 1 d . . . . .
H9A H 0.6523 0.7275 0.4547 0.024 Uiso 1 1 calc R U . . .
H9B H 0.6159 0.6005 0.4478 0.024 Uiso 1 1 calc R U . . .
C10 C 0.4237(3) 0.69697(17) 0.41626(5) 0.0151(4) Uani 1 1 d . . . . .
H10A H 0.3586 0.7692 0.4196 0.018 Uiso 1 1 calc R U . . .
H2 H 0.559(5) 0.467(3) 0.3485(7) 0.054(10) Uiso 1 1 d D . . . .
H5 H 0.087(3) 0.6990(17) 0.3763(7) 0.024(7) Uiso 1 1 d D . . . .
H1 H 0.161(4) 0.6539(17) 0.2790(6) 0.020(6) Uiso 1 1 d D . . . .
H10 H 0.636(4) 0.752(2) 0.3828(9) 0.042(9) Uiso 1 1 d D . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Br1 Cu1 2.3974(3) . ?
Cu1 O10 2.0038(14) . ?
Cu1 N5 2.0097(17) . ?
Cu1 N1 2.0193(16) . ?
Cu1 O2 2.2383(14) . ?
O2 C2 1.434(2) . ?
O2 H2 0.914(18) . ?
O10 C10 1.455(2) . ?
O10 H10 0.930(18) . ?
N1 C1 1.486(2) . ?
N1 C3 1.499(2) . ?
N1 H1 0.905(16) . ?
N5 C4 1.479(3) . ?
N5 C5 1.484(2) . ?
N5 H5 0.925(17) . ?
C1 C2 1.510(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.522(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.517(3) . ?
C5 C6 1.527(3) . ?
C5 H5A 1.0000 . ?
C6 C7 1.535(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.528(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.533(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.517(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 1.0000 . ?

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
O10 Cu1 N5 82.46(6) . . ?
O10 Cu1 N1 164.80(6) . . ?
N5 Cu1 N1 85.80(7) . . ?
O10 Cu1 O2 92.13(6) . . ?
N5 Cu1 O2 103.08(6) . . ?
N1 Cu1 O2 81.14(6) . . ?
O10 Cu1 Br1 97.98(4) . . ?
N5 Cu1 Br1 158.37(5) . . ?
N1 Cu1 Br1 96.50(5) . . ?
O2 Cu1 Br1 98.53(4) . . ?
C2 O2 Cu1 109.23(11) . . ?
C2 O2 H2 110(2) . . ?
Cu1 O2 H2 118(2) . . ?
C10 O10 Cu1 113.03(12) . . ?
C10 O10 H10 109(2) . . ?
Cu1 O10 H10 124(2) . . ?
C1 N1 C3 115.34(16) . . ?
C1 N1 Cu1 108.13(12) . . ?
C3 N1 Cu1 108.97(12) . . ?
C1 N1 H1 106.0(16) . . ?
C3 N1 H1 110.8(17) . . ?
Cu1 N1 H1 107.3(16) . . ?
C4 N5 C5 114.77(16) . . ?
C4 N5 Cu1 107.57(12) . . ?
C5 N5 Cu1 107.83(12) . . ?
C4 N5 H5 108.3(17) . . ?
C5 N5 H5 110.2(16) . . ?
Cu1 N5 H5 107.9(16) . . ?
N1 C1 C2 112.46(16) . . ?
N1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
O2 C2 C1 107.02(16) . . ?
O2 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 . . ?
O2 C2 H2B 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.6 . . ?
N1 C3 C4 110.56(16) . . ?
N1 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N5 C4 C3 108.22(16) . . ?
N5 C4 H4A 110.1 . . ?
C3 C4 H4A 110.1 . . ?
N5 C4 H4B 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
N5 C5 C10 106.76(16) . . ?
N5 C5 C6 114.68(17) . . ?
C10 C5 C6 111.30(16) . . ?
N5 C5 H5A 108.0 . . ?
C10 C5 H5A 108.0 . . ?
C6 C5 H5A 108.0 . . ?
C5 C6 C7 110.03(17) . . ?
C5 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
C7 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C6 111.32(18) . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C9 111.40(18) . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 108.66(17) . . ?
C10 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
C10 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.3 . . ?
O10 C10 C9 112.62(16) . . ?
O10 C10 C5 105.53(15) . . ?
C9 C10 C5 110.63(17) . . ?
O10 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C5 C10 H10A 109.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C2 -75.8(2) . . . . ?
Cu1 N1 C1 C2 46.40(19) . . . . ?
Cu1 O2 C2 C1 31.09(17) . . . . ?
N1 C1 C2 O2 -52.2(2) . . . . ?
C1 N1 C3 C4 95.72(19) . . . . ?
Cu1 N1 C3 C4 -26.06(19) . . . . ?
C5 N5 C4 C3 -163.28(16) . . . . ?
Cu1 N5 C4 C3 -43.29(18) . . . . ?
N1 C3 C4 N5 46.3(2) . . . . ?
C4 N5 C5 C10 166.86(16) . . . . ?
Cu1 N5 C5 C10 47.02(17) . . . . ?
C4 N5 C5 C6 -69.4(2) . . . . ?
Cu1 N5 C5 C6 170.79(14) . . . . ?
N5 C5 C6 C7 -177.12(17) . . . . ?
C10 C5 C6 C7 -55.8(2) . . . . ?
C5 C6 C7 C8 53.8(2) . . . . ?
C6 C7 C8 C9 -56.0(2) . . . . ?
C7 C8 C9 C10 58.1(2) . . . . ?
Cu1 O10 C10 C9 154.79(14) . . . . ?
Cu1 O10 C10 C5 34.00(18) . . . . ?
C8 C9 C10 O10 -177.46(17) . . . . ?
C8 C9 C10 C5 -59.6(2) . . . . ?
N5 C5 C10 O10 -52.3(2) . . . . ?
C6 C5 C10 O10 -178.12(16) . . . . ?
N5 C5 C10 C9 -174.37(16) . . . . ?
C6 C5 C10 C9 59.8(2) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 Br2 . . . 3.1554(15) 0.91(3) 2.25(3) 172(3) no
O10 H10 Br2 . . 6_765 3.1760(15) 0.93(3) 2.27(3) 165(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


