#------------------------------------------------------------------------------
#$Date: 2017-06-23 05:26:40 +0200 (vie 23 de jun de 2017) $
#$Revision: 198109 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/63/7056359.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7056359
loop_
_publ_author_name
'razali, mohd rizal'
'Zhan, Shun-Ze'
'Tai Wei, Chan'
_publ_section_title
;
 Solvent-mediated single-crystal-to-single-crystal transformation from
 dimeric to tetrameric copper(I) complex based on a substituted pyridine
 derived from the Diels-Alder adduct
;
_journal_name_full               'New J. Chem.'
_journal_paper_doi               10.1039/C7NJ01552F
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_sum            'C71 H51 Cu4 I4 N7 O6'
_chemical_formula_weight         1859.95
_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_Hall           'P 6c'
_space_group_name_H-M_alt        'P 63'
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-05-02 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   15.7192(13)
_cell_length_b                   15.7192(13)
_cell_length_c                   15.4669(19)
_cell_measurement_reflns_used    62174
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.10
_cell_measurement_theta_min      2.10
_cell_volume                     3309.7(6)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    X-SEED
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 Apex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            56597
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         1.496
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.192
_exptl_absorpt_correction_T_max  0.6273
_exptl_absorpt_correction_T_min  0.4261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1804
_exptl_crystal_size_max          0.571
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.099
_refine_diff_density_max         3.872
_refine_diff_density_min         -4.426
_refine_diff_density_rms         0.168
_refine_ls_abs_structure_details
;
 Flack x determined using 2078 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(12)
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         6427
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0118P)²+34.2677P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1165
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                5146
_reflns_number_total             6427
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj01552f1.cif
_cod_data_source_block           2
_cod_original_cell_volume        3309.7(7)
_cod_database_code               7056359
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.263
_shelx_estimated_absorpt_t_max   0.743
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/2'
'-y, x-y, z'
'-x, -y, z+1/2'
'-x+y, -x, z'
'y, -x+y, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
I1 I 0.51605(4) 0.15740(4) 0.97827(6) 0.02904(15) Uani 1 1 d . . .
I2 I 0.6667 0.3333 0.74264(9) 0.0536(5) Uani 1 3 d S T P
Cu2 Cu 0.6667 0.3333 1.02116(14) 0.0227(4) Uani 1 3 d S T P
Cu1 Cu 0.55949(10) 0.31409(10) 0.88214(11) 0.0348(3) Uani 1 1 d . . .
O1 O 0.1796(6) 0.2016(7) 0.5851(6) 0.0320(19) Uani 1 1 d . . .
O2 O 0.2303(7) 0.4640(6) 0.7515(7) 0.045(2) Uani 1 1 d . . .
N2 N 0.2280(7) 0.3348(7) 0.6780(6) 0.0274(19) Uani 1 1 d . . .
N3 N 0.6667 0.3333 1.1472(10) 0.026(3) Uani 1 3 d S T P
C3 C 0.3000(9) 0.3260(9) 0.7271(7) 0.030(2) Uani 1 1 d . . .
C9 C 0.1724(8) 0.2701(8) 0.6110(7) 0.026(2) Uani 1 1 d . . .
C23 C -0.0724(8) 0.2546(9) 0.5657(8) 0.030(2) Uani 1 1 d . . .
N1 N 0.4424(8) 0.3080(8) 0.8203(7) 0.039(2) Uani 1 1 d . . .
C11 C -0.0017(9) 0.2836(9) 0.7354(7) 0.032(3) Uani 1 1 d . . .
C17 C -0.0065(8) 0.2155(9) 0.5953(7) 0.029(2) Uani 1 1 d . . .
H17 H -0.0216 0.1536 0.5644 0.035 Uiso 1 1 calc R U .
C7 C 0.1202(8) 0.3891(8) 0.6290(7) 0.025(2) Uani 1 1 d D . .
C18 C -0.0526(9) 0.3404(10) 0.6092(8) 0.034(3) Uani 1 1 d . . .
C6 C 0.1992(8) 0.4044(8) 0.6949(7) 0.031(2) Uani 1 1 d . . .
C16 C -0.0181(9) 0.2010(9) 0.6907(8) 0.032(2) Uani 1 1 d . . .
C8 C 0.1007(7) 0.2993(8) 0.5785(7) 0.0232(19) Uani 1 1 d . . .
C10 C 0.0261(9) 0.3716(9) 0.6772(8) 0.035(3) Uani 1 1 d D . .
H10 H 0.0364 0.4308 0.7101 0.042 Uiso 1 1 calc R U .
C22 C -0.1450(8) 0.2127(10) 0.5033(8) 0.038(3) Uani 1 1 d . . .
H22 H -0.1570 0.1547 0.4737 0.046 Uiso 1 1 calc R U .
C21 C -0.2002(8) 0.2581(10) 0.4851(11) 0.045(3) Uani 1 1 d . . .
H21 H -0.2512 0.2303 0.4432 0.054 Uiso 1 1 calc R U .
C2 C 0.3183(10) 0.3531(11) 0.8099(8) 0.044(3) Uani 1 1 d . . .
H2 H 0.2815 0.3775 0.8387 0.053 Uiso 1 1 calc R U .
C4 C 0.3511(10) 0.2827(10) 0.6888(9) 0.040(3) Uani 1 1 d . . .
H4 H 0.3374 0.2586 0.6312 0.048 Uiso 1 1 calc R U .
C13 C -0.0314(11) 0.1940(14) 0.8668(9) 0.061(5) Uani 1 1 d . . .
H13 H -0.0342 0.1917 0.9282 0.073 Uiso 1 1 calc R U .
C12 C -0.0084(10) 0.2800(12) 0.8251(9) 0.046(3) Uani 1 1 d . . .
H12 H 0.0029 0.3363 0.8571 0.055 Uiso 1 1 calc R U .
C25 C 0.6667 0.3333 1.3164(12) 0.034(4) Uani 1 3 d S T P
H25A H 0.6240 0.2663 1.3376 0.050 Uiso 0.3333 1 calc R U P
H25B H 0.6423 0.3760 1.3376 0.050 Uiso 0.3333 1 calc R U P
H25C H 0.7337 0.3577 1.3376 0.050 Uiso 0.3333 1 calc R U P
C1 C 0.3921(11) 0.3453(10) 0.8544(8) 0.042(3) Uani 1 1 d . . .
H1 H 0.4063 0.3683 0.9123 0.051 Uiso 1 1 calc R U .
C5 C 0.4214(10) 0.2766(10) 0.7378(9) 0.045(3) Uani 1 1 d . . .
H5 H 0.4568 0.2488 0.7119 0.054 Uiso 1 1 calc R U .
C19 C -0.1073(10) 0.3851(11) 0.5892(9) 0.042(3) Uani 1 1 d . . .
H19 H -0.0946 0.4440 0.6175 0.050 Uiso 1 1 calc R U .
C15 C -0.0425(9) 0.1127(10) 0.7344(9) 0.043(3) Uani 1 1 d . . .
H15 H -0.0529 0.0561 0.7033 0.052 Uiso 1 1 calc R U .
C20 C -0.1812(10) 0.3420(12) 0.5271(10) 0.052(4) Uani 1 1 d . . .
H20 H -0.2192 0.3719 0.5137 0.063 Uiso 1 1 calc R U .
C14 C -0.0506(11) 0.1107(12) 0.8211(10) 0.055(4) Uani 1 1 d . . .
H14 H -0.0699 0.0512 0.8513 0.065 Uiso 1 1 calc R U .
C24 C 0.6667 0.3333 1.2212(12) 0.016(3) Uani 1 3 d S T P
H7 H 0.134(4) 0.447(4) 0.598(5) 0.01(2) Uiso 1 1 d D . .
H8 H 0.096(7) 0.300(7) 0.522(6) 0.00(2) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
Cu1 I1 Cu2 59.72(5) . .
Cu1 I1 Cu1 59.76(6) . 3_655
Cu2 I1 Cu1 58.59(5) . 3_655
Cu1 I2 Cu1 60.86(6) 3_655 5_665
Cu1 I2 Cu1 60.86(6) 3_655 .
Cu1 I2 Cu1 60.86(6) 5_665 .
N3 Cu2 Cu1 144.11(4) . 3_655
N3 Cu2 Cu1 144.11(4) . 5_665
Cu1 Cu2 Cu1 61.01(7) 3_655 5_665
N3 Cu2 Cu1 144.11(4) . .
Cu1 Cu2 Cu1 61.02(7) 3_655 .
Cu1 Cu2 Cu1 61.02(7) 5_665 .
N3 Cu2 I1 104.37(5) . 3_655
Cu1 Cu2 I1 59.84(4) 3_655 3_655
Cu1 Cu2 I1 62.14(5) 5_665 3_655
Cu1 Cu2 I1 111.50(8) . 3_655
N3 Cu2 I1 104.37(5) . .
Cu1 Cu2 I1 62.14(5) 3_655 .
Cu1 Cu2 I1 111.50(8) 5_665 .
Cu1 Cu2 I1 59.85(4) . .
I1 Cu2 I1 114.06(4) 3_655 .
N3 Cu2 I1 104.37(5) . 5_665
Cu1 Cu2 I1 111.50(8) 3_655 5_665
Cu1 Cu2 I1 59.85(4) 5_665 5_665
Cu1 Cu2 I1 62.14(5) . 5_665
I1 Cu2 I1 114.06(4) 3_655 5_665
I1 Cu2 I1 114.06(4) . 5_665
N1 Cu1 Cu2 153.5(3) . .
N1 Cu1 I1 114.4(3) . .
Cu2 Cu1 I1 60.44(4) . .
N1 Cu1 I2 97.5(3) . .
Cu2 Cu1 I2 108.32(6) . .
I1 Cu1 I2 114.45(6) . .
N1 Cu1 Cu1 134.8(3) . 5_665
Cu2 Cu1 Cu1 59.49(4) . 5_665
I1 Cu1 Cu1 110.72(5) . 5_665
I2 Cu1 Cu1 59.57(3) . 5_665
N1 Cu1 Cu1 144.3(3) . 3_655
Cu2 Cu1 Cu1 59.49(4) . 3_655
I1 Cu1 Cu1 61.82(6) . 3_655
I2 Cu1 Cu1 59.57(3) . 3_655
Cu1 Cu1 Cu1 60.0 5_665 3_655
N1 Cu1 I1 105.9(3) . 5_665
Cu2 Cu1 I1 59.27(4) . 5_665
I1 Cu1 I1 112.09(6) . 5_665
I2 Cu1 I1 111.47(5) . 5_665
Cu1 Cu1 I1 58.43(5) 5_665 5_665
Cu1 Cu1 I1 107.96(5) 3_655 5_665
C6 N2 C9 112.0(9) . .
C6 N2 C3 123.9(10) . .
C9 N2 C3 123.9(9) . .
C24 N3 Cu2 180.0 . .
C2 C3 C4 118.1(11) . .
C2 C3 N2 122.4(11) . .
C4 C3 N2 119.5(10) . .
O1 C9 N2 126.0(10) . .
O1 C9 C8 125.7(11) . .
N2 C9 C8 108.3(9) . .
C22 C23 C18 121.9(11) . .
C22 C23 C17 125.8(11) . .
C18 C23 C17 112.3(10) . .
C1 N1 C5 117.0(11) . .
C1 N1 Cu1 121.6(9) . .
C5 N1 Cu1 120.9(9) . .
C16 C11 C12 119.2(12) . .
C16 C11 C10 113.2(10) . .
C12 C11 C10 127.6(12) . .
C16 C17 C23 107.8(9) . .
C16 C17 C8 107.0(9) . .
C23 C17 C8 106.1(9) . .
C16 C17 H17 111.9 . .
C23 C17 H17 111.9 . .
C8 C17 H17 111.9 . .
C8 C7 C6 105.2(9) . .
C8 C7 C10 110.7(9) . .
C6 C7 C10 109.6(9) . .
C8 C7 H7 119(5) . .
C6 C7 H7 114(6) . .
C10 C7 H7 98.9(16) . .
C19 C18 C23 119.1(12) . .
C19 C18 C10 127.2(12) . .
C23 C18 C10 113.7(10) . .
O2 C6 N2 125.7(11) . .
O2 C6 C7 126.5(11) . .
N2 C6 C7 107.8(9) . .
C11 C16 C15 121.1(12) . .
C11 C16 C17 113.7(10) . .
C15 C16 C17 125.1(12) . .
C9 C8 C7 106.4(9) . .
C9 C8 C17 110.2(9) . .
C7 C8 C17 109.5(9) . .
C9 C8 H8 114(6) . .
C7 C8 H8 119(6) . .
C17 C8 H8 97(6) . .
C18 C10 C11 107.5(10) . .
C18 C10 C7 106.1(10) . .
C11 C10 C7 105.0(9) . .
C18 C10 H10 112.6 . .
C11 C10 H10 112.6 . .
C7 C10 H10 112.6 . .
C23 C22 C21 118.1(12) . .
C23 C22 H22 121.0 . .
C21 C22 H22 121.0 . .
C20 C21 C22 120.4(13) . .
C20 C21 H21 119.8 . .
C22 C21 H21 119.8 . .
C3 C2 C1 119.8(12) . .
C3 C2 H2 120.1 . .
C1 C2 H2 120.1 . .
C5 C4 C3 118.0(12) . .
C5 C4 H4 121.0 . .
C3 C4 H4 121.0 . .
C12 C13 C14 121.2(13) . .
C12 C13 H13 119.4 . .
C14 C13 H13 119.4 . .
C13 C12 C11 119.1(14) . .
C13 C12 H12 120.5 . .
C11 C12 H12 120.5 . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
N1 C1 C2 123.5(12) . .
N1 C1 H1 118.2 . .
C2 C1 H1 118.2 . .
N1 C5 C4 123.5(12) . .
N1 C5 H5 118.3 . .
C4 C5 H5 118.3 . .
C18 C19 C20 118.8(13) . .
C18 C19 H19 120.6 . .
C20 C19 H19 120.6 . .
C14 C15 C16 118.3(14) . .
C14 C15 H15 120.9 . .
C16 C15 H15 120.9 . .
C21 C20 C19 121.7(12) . .
C21 C20 H20 119.1 . .
C19 C20 H20 119.1 . .
C15 C14 C13 121.0(14) . .
C15 C14 H14 119.5 . .
C13 C14 H14 119.5 . .
N3 C24 C25 180.000(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 Cu1 2.6575(15) .
I1 Cu2 2.6733(8) .
I1 Cu1 2.7496(17) 3_655
I2 Cu1 2.660(2) 3_655
I2 Cu1 2.660(2) 5_665
I2 Cu1 2.660(2) .
Cu2 N3 1.949(16) .
Cu2 Cu1 2.654(2) 3_655
Cu2 Cu1 2.654(2) 5_665
Cu2 Cu1 2.654(2) .
Cu2 I1 2.6732(8) 3_655
Cu2 I1 2.6732(8) 5_665
Cu1 N1 2.033(11) .
Cu1 Cu1 2.695(2) 5_665
Cu1 Cu1 2.695(2) 3_655
Cu1 I1 2.7495(17) 5_665
O1 C9 1.206(14) .
O2 C6 1.194(14) .
N2 C6 1.403(14) .
N2 C9 1.408(15) .
N2 C3 1.427(13) .
N3 C24 1.14(2) .
C3 C2 1.335(17) .
C3 C4 1.416(17) .
C9 C8 1.500(14) .
C23 C22 1.385(16) .
C23 C18 1.395(18) .
C23 C17 1.515(15) .
N1 C1 1.308(17) .
N1 C5 1.347(16) .
C11 C16 1.376(17) .
C11 C12 1.390(17) .
C11 C10 1.521(17) .
C17 C16 1.491(16) .
C17 C8 1.557(15) .
C17 H17 1.0000 .
C7 C8 1.504(15) .
C7 C6 1.528(15) .
C7 C10 1.554(16) .
C7 H7 0.959(14) .
C18 C19 1.391(17) .
C18 C10 1.507(17) .
C16 C15 1.414(17) .
C8 H8 0.88(10) .
C10 H10 1.0000 .
C22 C21 1.402(16) .
C22 H22 0.9500 .
C21 C20 1.36(2) .
C21 H21 0.9500 .
C2 C1 1.406(19) .
C2 H2 0.9500 .
C4 C5 1.383(18) .
C4 H4 0.9500 .
C13 C12 1.37(2) .
C13 C14 1.38(2) .
C13 H13 0.9500 .
C12 H12 0.9500 .
C25 C24 1.47(3) .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C1 H1 0.9500 .
C5 H5 0.9500 .
C19 C20 1.39(2) .
C19 H19 0.9500 .
C15 C14 1.35(2) .
C15 H15 0.9500 .
C20 H20 0.9500 .
C14 H14 0.9500 .
