#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:56:56 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179605 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/69/4506926.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_4506926
loop_
_publ_author_name
'Blake, Karyn M.'
'Gandolfo, Chaun M.'
'Uebler, Jacob W.'
'LaDuca, Robert L.'
_publ_section_title
;
 Diverse Topologies in Chiral Divalent Metal Camphorate Coordination
 Polymers Containing 4,4′-Dipyridylamine
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5125
_journal_paper_doi               10.1021/cg301091f
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C30 H39 Cu2 N3 O9'
_chemical_formula_weight         712.72
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2011-02-09 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 106.562(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.868(6)
_cell_length_b                   12.860(4)
_cell_length_c                   13.360(4)
_cell_measurement_reflns_used    7617
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.58
_cell_measurement_theta_min      2.25
_cell_volume                     3107.2(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_sigmaI/netI    0.0665
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22122
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    1.426
_exptl_absorpt_correction_T_max  0.8800
_exptl_absorpt_correction_T_min  0.6621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.570
_refine_diff_density_min         -1.200
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.37(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5724
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.0803
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1437P)²+1.1139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2245
_refine_ls_wR_factor_ref         0.2501
_reflns_number_gt                3525
_reflns_number_total             5724
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301091f_si_003.cif
_cod_data_source_block           5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        3107.3(18)
_cod_original_sg_symbol_H-M      C2
_cod_database_code               4506926
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu 0.82047(10) 0.50596(10) 0.26586(15) 0.0914(7) Uani 1 1 d .
Cu2 Cu 0.67936(7) 0.56376(6) 0.23116(9) 0.0597(4) Uani 1 1 d .
O1 O 0.7786(5) 0.1962(6) -0.1987(5) 0.068(2) Uani 1 1 d .
O1W O 1.0000 0.1037(14) 0.0000 0.186(10) Uani 1 2 d S
H1W H 0.9566 0.0804 -0.0270 0.224 Uiso 1 1 d R
O2 O 0.6634(6) 0.1432(8) -0.2255(7) 0.087(3) Uani 1 1 d .
O2W O 0.5000 0.9794(13) 0.5000 0.131(6) Uani 1 2 d S
H2W H 0.5442 1.0015 0.5209 0.157 Uiso 1 1 d R
O3 O 0.7674(4) 0.4780(7) 0.1015(5) 0.071(2) Uani 1 1 d .
O4 O 0.6489(4) 0.5242(6) 0.0925(4) 0.068(2) Uani 1 1 d .
O5 O 0.7761(6) 0.3760(7) 0.2936(7) 0.090(3) Uani 1 1 d .
O6 O 0.6584(5) 0.4226(6) 0.2659(6) 0.073(2) Uani 1 1 d .
O7 O 0.7530(11) 0.0844(8) 0.6134(8) 0.154(7) Uani 1 1 d .
O8 O 0.6378(10) 0.0483(13) 0.5632(15) 0.220(10) Uani 1 1 d .
N1 N 0.9080(8) 0.4347(15) 0.2178(9) 0.111(5) Uani 1 1 d .
N2 N 0.5905(6) 0.6313(6) 0.2724(7) 0.065(3) Uani 1 1 d .
N3 N 1.0000 0.3090(15) 0.0000 0.109(6) Uani 1 2 d SD
H3N H 1.0000 0.2396 0.0000 0.131 Uiso 1 2 d SRD
N4 N 0.5000 0.7564(9) 0.5000 0.054(3) Uani 1 2 d SD
H4N H 0.5000 0.8250 0.5000 0.064 Uiso 1 2 d SRD
C1 C 0.5997(9) 0.7337(12) 0.3052(10) 0.092(5) Uani 1 1 d .
H1 H 0.6279 0.7775 0.2739 0.111 Uiso 1 1 calc R
C2 C 0.5708(6) 0.7779(10) 0.3810(7) 0.059(3) Uani 1 1 d .
H2 H 0.5775 0.8494 0.3989 0.071 Uiso 1 1 calc R
C3 C 0.5327(6) 0.7134(10) 0.4278(8) 0.061(3) Uani 1 1 d .
C4 C 0.5141(6) 0.6096(9) 0.3874(7) 0.058(3) Uani 1 1 d .
H4 H 0.4799 0.5668 0.4087 0.069 Uiso 1 1 calc R
C5 C 0.5486(5) 0.5780(8) 0.3174(8) 0.059(3) Uani 1 1 d .
H5 H 0.5417 0.5069 0.2977 0.071 Uiso 1 1 calc R
C6 C 0.9519(12) 0.5000(17) 0.1811(13) 0.133(8) Uani 1 1 d .
H6 H 0.9621 0.5690 0.2065 0.159 Uiso 1 1 calc R
C7 C 0.7627(11) 0.0954(18) 0.4184(15) 0.138(7) Uiso 1 1 d .
H7A H 0.7715 0.0210 0.4071 0.165 Uiso 1 1 calc R
H7B H 0.8017 0.1210 0.4798 0.165 Uiso 1 1 calc R
C8 C 0.9814(8) 0.4595(16) 0.1036(14) 0.111(6) Uani 1 1 d .
H8 H 1.0033 0.5072 0.0668 0.133 Uiso 1 1 calc R
C9 C 0.9809(7) 0.3566(11) 0.0771(10) 0.072(3) Uani 1 1 d .
C10 C 0.9349(9) 0.2979(12) 0.1252(13) 0.094(5) Uani 1 1 d .
H10 H 0.9268 0.2267 0.1064 0.113 Uiso 1 1 calc R
C11 C 0.9021(8) 0.3360(10) 0.1953(10) 0.082(4) Uani 1 1 d .
H11 H 0.8752 0.2913 0.2278 0.098 Uiso 1 1 calc R
C12 C 0.7124(8) 0.3579(9) 0.2951(8) 0.065(3) Uani 1 1 d .
C13 C 0.6883(7) 0.2456(10) 0.3117(10) 0.080(4) Uani 1 1 d .
H13 H 0.6443 0.2259 0.2528 0.096 Uiso 1 1 calc R
C14 C 0.7588(13) 0.1643(12) 0.3149(16) 0.178(12) Uani 1 1 d .
H14A H 0.7481 0.1204 0.2515 0.214 Uiso 1 1 calc R
H14B H 0.8055 0.2028 0.3223 0.214 Uiso 1 1 calc R
C15 C 0.6888(10) 0.1123(13) 0.4303(13) 0.135(8) Uani 1 1 d .
C16 C 0.6962(8) 0.0820(10) 0.5524(9) 0.073(4) Uani 1 1 d .
C17 C 0.7091(12) 0.2149(12) -0.2076(11) 0.107(7) Uani 1 1 d .
C18 C 0.6937(10) 0.3228(10) -0.1831(8) 0.114(7) Uani 1 1 d D
C19 C 0.6338(13) 0.3735(13) -0.2779(9) 0.175(10) Uani 1 1 d .
H19A H 0.6225 0.4439 -0.2590 0.263 Uiso 1 1 calc R
H19B H 0.5887 0.3313 -0.2950 0.263 Uiso 1 1 calc R
H19C H 0.6531 0.3768 -0.3387 0.263 Uiso 1 1 calc R
C20 C 0.7023(14) 0.4911(13) 0.057(3) 0.234(18) Uani 1 1 d .
C21 C 0.6717(9) 0.2303(10) 0.4117(13) 0.102(5) Uani 1 1 d .
C22 C 0.7268(9) 0.2951(11) 0.5018(9) 0.090(5) Uani 1 1 d .
H22A H 0.7778 0.2817 0.5010 0.134 Uiso 1 1 calc R
H22B H 0.7208 0.2742 0.5695 0.134 Uiso 1 1 calc R
H22C H 0.7159 0.3694 0.4907 0.134 Uiso 1 1 calc R
C23 C 0.6832(7) 0.4587(9) -0.0600(8) 0.067(3) Uani 1 1 d .
H23 H 0.6398 0.4967 -0.1059 0.080 Uiso 1 1 calc R
C24 C 0.7654(17) 0.484(2) -0.0897(15) 0.251(18) Uani 1 1 d .
H24A H 0.7615 0.5458 -0.1347 0.301 Uiso 1 1 calc R
H24B H 0.8073 0.4924 -0.0259 0.301 Uiso 1 1 calc R
C25 C 0.7717(11) 0.3929(12) -0.1427(19) 0.189(13) Uani 1 1 d D
H25A H 0.8105 0.3488 -0.0964 0.226 Uiso 1 1 calc R
H25B H 0.7884 0.4111 -0.2043 0.226 Uiso 1 1 calc R
C26 C 0.6813(16) 0.3471(11) -0.0794(8) 0.205(14) Uani 1 1 d .
C27 C 0.5917(8) 0.2593(12) 0.379(2) 0.201(13) Uani 1 1 d .
H27A H 0.5696 0.2426 0.4346 0.302 Uiso 1 1 calc R
H27B H 0.5663 0.2204 0.3155 0.302 Uiso 1 1 calc R
H27C H 0.5869 0.3340 0.3638 0.302 Uiso 1 1 calc R
C28 C 0.5959(12) 0.346(3) -0.084(4) 0.38(3) Uani 1 1 d .
H28A H 0.5690 0.3953 -0.1378 0.565 Uiso 1 1 calc R
H28B H 0.5903 0.3665 -0.0163 0.565 Uiso 1 1 calc R
H28C H 0.5758 0.2760 -0.1021 0.565 Uiso 1 1 calc R
C29 C 0.6482(12) 0.0405(13) 0.3639(13) 0.157(9) Uani 1 1 d .
H29A H 0.6646 -0.0294 0.3895 0.236 Uiso 1 1 calc R
H29B H 0.6547 0.0501 0.2943 0.236 Uiso 1 1 calc R
H29C H 0.5958 0.0488 0.3600 0.236 Uiso 1 1 calc R
C30 C 0.7236(10) 0.2745(10) 0.0005(10) 0.106(6) Uani 1 1 d .
H30A H 0.7766 0.2858 0.0114 0.158 Uiso 1 1 calc R
H30B H 0.7108 0.2028 -0.0227 0.158 Uiso 1 1 calc R
H30C H 0.7114 0.2865 0.0662 0.158 Uiso 1 1 calc R
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'
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
O2 Cu1 O5 164.6(5) 4_655 .
O2 Cu1 N1 96.5(6) 4_655 .
O5 Cu1 N1 95.8(6) . .
O2 Cu1 O3 86.1(4) 4_655 .
O5 Cu1 O3 87.2(4) . .
N1 Cu1 O3 78.4(3) . .
O2 Cu1 O8 91.5(5) 4_655 4_656
O5 Cu1 O8 93.4(5) . 4_656
N1 Cu1 O8 109.3(5) . 4_656
O3 Cu1 O8 172.2(5) . 4_656
O2 Cu1 Cu2 85.7(3) 4_655 .
O5 Cu1 Cu2 79.1(3) . .
N1 Cu1 Cu2 151.9(3) . .
O3 Cu1 Cu2 73.8(2) . .
O8 Cu1 Cu2 98.7(4) 4_656 .
O4 Cu2 O6 87.5(3) . .
O4 Cu2 O1 92.7(3) . 4_655
O6 Cu2 O1 168.1(4) . 4_655
O4 Cu2 N2 109.5(4) . .
O6 Cu2 N2 95.3(3) . .
O1 Cu2 N2 95.9(3) 4_655 .
O4 Cu2 O7 160.8(5) . 4_656
O6 Cu2 O7 89.4(4) . 4_656
O1 Cu2 O7 86.6(4) 4_655 4_656
N2 Cu2 O7 89.7(5) . 4_656
O4 Cu2 Cu1 96.2(2) . .
O6 Cu2 Cu1 87.7(3) . .
O1 Cu2 Cu1 80.5(2) 4_655 .
N2 Cu2 Cu1 154.3(3) . .
O7 Cu2 Cu1 64.8(4) 4_656 .
C17 O1 Cu2 126.5(10) . 4_645
C17 O2 Cu1 126.1(10) . 4_645
C20 O3 Cu1 125.9(16) . .
C20 O4 Cu2 113.9(18) . .
C12 O5 Cu1 129.7(9) . .
C12 O6 Cu2 118.6(8) . .
C16 O7 Cu2 150.7(11) . 4_646
C16 O8 Cu1 98.0(13) . 4_646
C11 N1 C6 122.6(18) . .
C11 N1 Cu1 117.6(14) . .
C6 N1 Cu1 116.3(16) . .
C5 N2 C1 112.9(8) . .
C5 N2 Cu2 122.3(7) . .
C1 N2 Cu2 116.1(8) . .
C9 N3 C9 125(2) . 2_755
C3 N4 C3 133.4(14) 2_656 .
N2 C1 C2 125.2(11) . .
C3 C2 C1 116.8(12) . .
C2 C3 N4 118.0(12) . .
C2 C3 C4 119.7(10) . .
N4 C3 C4 121.0(11) . .
C5 C4 C3 115.1(11) . .
N2 C5 C4 129.4(10) . .
N1 C6 C8 116.3(19) . .
C15 C7 C14 101.4(15) . .
C9 C8 C6 125.0(18) . .
N3 C9 C8 131.3(16) . .
N3 C9 C10 115.9(13) . .
C8 C9 C10 110.7(14) . .
C11 C10 C9 125.1(14) . .
N1 C11 C10 119.1(16) . .
O5 C12 O6 124.5(12) . .
O5 C12 C13 120.4(11) . .
O6 C12 C13 114.0(12) . .
C21 C13 C12 113.7(11) . .
C21 C13 C14 105.4(11) . .
C12 C13 C14 108.8(11) . .
C7 C14 C13 101.8(12) . .
C29 C15 C7 102(2) . .
C29 C15 C21 120.5(14) . .
C7 C15 C21 106.8(15) . .
C29 C15 C16 111.1(13) . .
C7 C15 C16 105.0(11) . .
C21 C15 C16 110.2(16) . .
O7 C16 O8 127.7(14) . .
O7 C16 C15 119.8(12) . .
O8 C16 C15 112.0(15) . .
O2 C17 O1 120.4(13) . .
O2 C17 C18 125.0(16) . .
O1 C17 C18 114.3(18) . .
C17 C18 C26 119.5(10) . .
C17 C18 C19 110.6(13) . .
C26 C18 C19 113.0(14) . .
C17 C18 C25 111.5(16) . .
C26 C18 C25 86.8(13) . .
C19 C18 C25 113.4(13) . .
O3 C20 O4 130(3) . .
O3 C20 C23 111.7(14) . .
O4 C20 C23 118(2) . .
C13 C21 C27 99.0(16) . .
C13 C21 C15 100.8(12) . .
C27 C21 C15 115.9(14) . .
C13 C21 C22 110.8(11) . .
C27 C21 C22 118.9(14) . .
C15 C21 C22 109.3(14) . .
C26 C23 C20 115.5(9) . .
C26 C23 C24 96.9(18) . .
C20 C23 C24 102.3(13) . .
C25 C24 C23 99.9(13) . .
C24 C25 C18 114.9(15) . .
C23 C26 C30 121.0(13) . .
C23 C26 C18 111.5(14) . .
C30 C26 C18 110.1(14) . .
C23 C26 C28 89(2) . .
C30 C26 C28 111(2) . .
C18 C26 C28 112(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.895(10) 4_655
Cu1 O5 1.951(10) .
Cu1 N1 2.142(16) .
Cu1 O3 2.168(7) .
Cu1 O8 2.259(18) 4_656
Cu1 Cu2 2.6743(18) .
Cu2 O4 1.848(6) .
Cu2 O6 1.943(8) .
Cu2 O1 1.978(8) 4_655
Cu2 N2 2.096(8) .
Cu2 O7 2.121(15) 4_656
O1 C17 1.304(19) .
O1 Cu2 1.978(8) 4_645
O2 C17 1.24(2) .
O2 Cu1 1.895(10) 4_645
O3 C20 1.21(3) .
O4 C20 1.304(17) .
O5 C12 1.231(15) .
O6 C12 1.286(13) .
O7 C16 1.147(19) .
O7 Cu2 2.121(15) 4_646
O8 C16 1.230(19) .
O8 Cu1 2.259(18) 4_646
N1 C11 1.30(2) .
N1 C6 1.36(2) .
N2 C5 1.315(11) .
N2 C1 1.383(17) .
N3 C9 1.333(15) .
N3 C9 1.333(15) 2_755
N4 C3 1.399(11) 2_656
N4 C3 1.399(11) .
C1 C2 1.400(14) .
C2 C3 1.361(16) .
C3 C4 1.445(17) .
C4 C5 1.346(12) .
C6 C8 1.41(3) .
C7 C15 1.46(2) .
C7 C14 1.63(2) .
C8 C9 1.37(2) .
C9 C10 1.433(18) .
C10 C11 1.353(18) .
C12 C13 1.548(17) .
C13 C21 1.472(18) .
C13 C14 1.68(2) .
C15 C29 1.36(2) .
C15 C21 1.56(2) .
C15 C16 1.644(18) .
C17 C18 1.473(19) .
C18 C26 1.503(18) .
C18 C19 1.579(19) .
C18 C25 1.678(17) .
C20 C23 1.55(4) .
C21 C27 1.49(2) .
C21 C22 1.58(2) .
C23 C26 1.457(18) .
C23 C24 1.74(2) .
C24 C25 1.39(3) .
C26 C30 1.470(16) .
C26 C28 1.59(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3N O1W 0.89 1.75 2.64(3) 180.0 .
N4 H4N O2W 0.88 1.98 2.87(2) 180.0 .
O1W H1W O4 0.85 2.06 2.913(10) 179.8 4_645
O2W H2W O8 0.85 1.80 2.648(19) 179.2 1_565
