#------------------------------------------------------------------------------
#$Date: 2020-07-06 05:09:14 +0200 (lun 06 de jul de 2020) $
#$Revision: 253904 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/46/7704619.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_7704619
loop_
_publ_author_name
'Lopera, Alberto'
'Gil-Martínez, Ariadna'
'Pitarch-Jarque, Javier'
'Verdejo, Begoña'
'Blasco, Salvador'
'Clares, M. Paz'
'Jiménez, Hermas R'
'García-España, Enrique'
_publ_section_title
;
 Influence of the chain length and metal : ligand ratio on
 the self-organization processes of Cu²⁺ complexes of [1 + 1]
 1H-pyrazole azamacrocycles.
;
_journal_issue                   25
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8614
_journal_page_last               8624
_journal_paper_doi               10.1039/d0dt01056a
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C12 H23 Cu N6, Cl O4'
_chemical_formula_sum            'C12 H23 Cl Cu N6 O4'
_chemical_formula_weight         414.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-05-29
_audit_creation_method
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-01 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.643(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1975(7)
_cell_length_b                   8.9313(5)
_cell_length_c                   16.2321(11)
_cell_measurement_reflns_used    5226
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      29.33
_cell_measurement_theta_min      2.51
_cell_volume                     1621.62(17)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(1)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            73857
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         45.395
_diffrn_reflns_theta_min         2.919
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.544
_exptl_absorpt_correction_T_max  0.7489
_exptl_absorpt_correction_T_min  0.6375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0754 before and 0.0514 after correction.
The Ratio of minimum to maximum transmission is 0.8512.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear dark black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.366
_exptl_crystal_size_mid          0.333
_exptl_crystal_size_min          0.326
_refine_diff_density_max         0.798
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         13349
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0360P)²+0.4221P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0882
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10331
_reflns_number_total             13349
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt01056a2.cif
_cod_data_source_block           2_hexa
_cod_depositor_comments
'Adding full bibliography for 7704616--7704620.cif.'
_cod_database_code               7704619
_shelx_shelxl_version_number     2018/3
_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_max   0.633
_shelx_estimated_absorpt_t_min   0.602
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
2. Restrained distances
 C9B-C8B \\sim C9-C8
 with sigma of 0.02
 Cl2-O23 \\sim Cl2-O24 \\sim Cl2-O22 \\sim Cl2-O21
 with sigma of 0.02
3. Others
 Sof(H7BC)=Sof(H7BD)=Sof(C9B)=Sof(H9BA)=Sof(H9BB)=Sof(C8B)=Sof(H8BA)=Sof(H8BB)=
 Sof(C10B)=Sof(H10C)=Sof(H10D)=Sof(N5B)=Sof(H5BA)=1-FVAR(1)
 Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C9)=Sof(H9A)=
 Sof(H9B)=Sof(H7A)=Sof(H7B)=Sof(N5)=Sof(H5)=FVAR(1)
 Sof(Cl2)=Sof(O21)=Sof(O24)=Sof(O22)=Sof(O23)=1-FVAR(2)
 Sof(Cl1)=Sof(O11)=Sof(O12)=Sof(O14)=Sof(O13)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 N5(H5), N5B(H5BA)
4.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C8(H8A,H8B), C6(H6A,H6B), C10(H10A,H10B), C9(H9A,H9B), C1(H1A,
 H1B), C12(H12A,H12B), C7(H7A,H7B), C7(H7BC,H7BD), C9B(H9BA,H9BB), C8B(H8BA,
 H8BB), C10B(H10C,H10D)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_olex2_date_sample_completion    2020-01-16
_olex2_date_sample_data_collection 2020-01-16
_olex2_date_sample_submission    2020-01-16
_olex2_submission_original_sample_id al2
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.67451(2) 0.52894(2) 0.49083(2) 0.01133(2) Uani 1 1 d . . . . .
Cl1 Cl -0.00548(11) 0.83151(13) 0.37533(10) 0.0168(3) Uani 0.72(2) 1 d . . P A
1
N2 N 0.42930(6) 0.64148(7) 0.53263(4) 0.01199(9) Uani 1 1 d . . . . .
N3 N 0.54760(6) 0.66103(7) 0.52591(4) 0.01205(9) Uani 1 1 d . . . . .
N6 N 0.32932(7) 0.36189(8) 0.65469(5) 0.01637(11) Uani 1 1 d . . . . .
O11 O -0.1264(4) 0.8869(7) 0.3807(4) 0.0227(5) Uani 0.72(2) 1 d . . P A 1
O12 O 0.0112(5) 0.7178(5) 0.4404(3) 0.0206(5) Uani 0.72(2) 1 d . . P A 1
N4 N 0.78093(6) 0.70878(8) 0.53365(4) 0.01458(10) Uani 1 1 d . . . . .
O14 O 0.0018(4) 0.7571(4) 0.2965(2) 0.0322(6) Uani 0.72(2) 1 d . . P A 1
C5 C 0.70484(8) 0.84272(9) 0.54741(6) 0.01806(14) Uani 1 1 d . . . . .
H5A H 0.712277 0.914050 0.501242 0.022 Uiso 1 1 calc R . . . .
H5B H 0.732745 0.893560 0.598967 0.022 Uiso 1 1 calc R . . . .
C8 C 0.66666(9) 0.33604(11) 0.67070(6) 0.01869(17) Uani 0.931(3) 1 d D . P B 1
H8A H 0.704440 0.314302 0.725741 0.022 Uiso 0.931(3) 1 calc R . P B 1
H8B H 0.654989 0.239831 0.641125 0.022 Uiso 0.931(3) 1 calc R . P B 1
C6 C 0.85428(8) 0.66373(11) 0.60812(6) 0.01968(14) Uani 1 1 d . . . . .
H6A H 0.885013 0.754563 0.636907 0.024 Uiso 1 1 calc R . . . .
H6B H 0.923785 0.604689 0.591085 0.024 Uiso 1 1 calc R . . . .
C3 C 0.47420(7) 0.87089(9) 0.57878(5) 0.01579(12) Uani 1 1 d . . . . .
H3 H 0.467929 0.968842 0.600986 0.019 Uiso 1 1 calc R . . . .
C10 C 0.44259(13) 0.30042(15) 0.68935(9) 0.01815(19) Uani 0.931(3) 1 d . . P B
1
H10A H 0.460889 0.206110 0.660468 0.022 Uiso 0.931(3) 1 calc R . P B 1
H10B H 0.434083 0.276776 0.748379 0.022 Uiso 0.931(3) 1 calc R . P B 1
C9 C 0.54563(8) 0.41001(10) 0.68099(6) 0.01550(16) Uani 0.931(3) 1 d D . P B 1
H9A H 0.527457 0.475340 0.632756 0.019 Uiso 0.931(3) 1 calc R . P B 1
H9B H 0.551057 0.474596 0.730590 0.019 Uiso 0.931(3) 1 calc R . P B 1
C1 C 0.25033(7) 0.76779(9) 0.57121(6) 0.01678(13) Uani 1 1 d . . . . .
H1A H 0.230299 0.816552 0.623574 0.020 Uiso 1 1 calc R . . . .
H1B H 0.212654 0.826138 0.525121 0.020 Uiso 1 1 calc R . . . .
C12 C 0.17550(8) 0.55438(10) 0.65202(6) 0.01777(13) Uani 1 1 d . . . . .
H12A H 0.114473 0.474460 0.645935 0.021 Uiso 1 1 calc R . . . .
H12B H 0.141504 0.636566 0.684496 0.021 Uiso 1 1 calc R . . . .
C4 C 0.57687(7) 0.79812(8) 0.55330(5) 0.01345(11) Uani 1 1 d . . . . .
C2 C 0.38316(7) 0.76617(8) 0.56402(5) 0.01304(11) Uani 1 1 d . . . . .
C7 C 0.78316(8) 0.57154(11) 0.66693(5) 0.01943(14) Uani 1 1 d . . . . .
H7A H 0.832842 0.548146 0.717313 0.023 Uiso 0.931(3) 1 calc R . P B 1
H7B H 0.711972 0.628144 0.683191 0.023 Uiso 0.931(3) 1 calc R . P B 1
H7BC H 0.838470 0.542772 0.713592 0.023 Uiso 0.069(3) 1 calc R . P B 2
H7BD H 0.722435 0.638682 0.689570 0.023 Uiso 0.069(3) 1 calc R . P B 2
C11 C 0.28564(8) 0.49260(10) 0.69846(5) 0.01749(13) Uani 1 1 d . . . . .
N1 N 0.20295(6) 0.61156(8) 0.56912(4) 0.01412(10) Uani 1 1 d . . . . .
O13 O 0.0830(4) 0.9434(7) 0.3835(3) 0.0506(9) Uani 0.72(2) 1 d . . P A 1
N5 N 0.74623(10) 0.43250(13) 0.62454(8) 0.01569(16) Uani 0.931(3) 1 d . . P B 1
H5 H 0.820453 0.373698 0.615391 0.019 Uiso 0.931(3) 1 calc R . P B 1
H1 H 0.1365(14) 0.6140(18) 0.5394(10) 0.023(4) Uiso 1 1 d . . . . .
H4 H 0.8329(13) 0.7370(18) 0.4973(9) 0.018(3) Uiso 1 1 d . . . . .
H11A H 0.3520(13) 0.5687(16) 0.7010(9) 0.014(3) Uiso 1 1 d . . . . .
H11B H 0.2642(15) 0.4666(17) 0.7548(10) 0.024(4) Uiso 1 1 d . . . . .
C9B C 0.5487(12) 0.2755(15) 0.6604(8) 0.019(2) Uani 0.069(3) 1 d D . P B 2
H9BA H 0.540489 0.263024 0.599829 0.023 Uiso 0.069(3) 1 calc R . P B 2
H9BB H 0.601499 0.194373 0.682310 0.023 Uiso 0.069(3) 1 calc R . P B 2
C8B C 0.6065(12) 0.4185(18) 0.6784(9) 0.028(3) Uani 0.069(3) 1 d D . P B 2
H8BA H 0.621134 0.428600 0.738762 0.033 Uiso 0.069(3) 1 calc R . P B 2
H8BB H 0.552570 0.500709 0.659593 0.033 Uiso 0.069(3) 1 calc R . P B 2
C10B C 0.433(2) 0.258(2) 0.694(2) 0.033(5) Uani 0.069(3) 1 d . . P B 2
H10C H 0.440838 0.277824 0.753755 0.040 Uiso 0.069(3) 1 calc R . P B 2
H10D H 0.408464 0.152044 0.686580 0.040 Uiso 0.069(3) 1 calc R . P B 2
N5B N 0.719(2) 0.432(3) 0.6380(14) 0.037(5) Uani 0.069(3) 1 d . . P B 2
H5BA H 0.769829 0.339277 0.641059 0.044 Uiso 0.069(3) 1 calc R . P B 2
H6 H 0.2746(16) 0.295(2) 0.6562(11) 0.033(4) Uiso 1 1 d . . . . .
Cl2 Cl -0.0042(4) 0.8424(9) 0.3824(5) 0.0365(9) Uani 0.28(2) 1 d D . P A 2
O21 O 0.0212(18) 0.783(2) 0.3043(9) 0.064(4) Uani 0.28(2) 1 d D . P A 2
O24 O 0.0746(15) 0.9604(18) 0.4047(15) 0.080(5) Uani 0.28(2) 1 d D . P A 2
O22 O -0.1173(12) 0.906(2) 0.3824(11) 0.033(3) Uani 0.28(2) 1 d D . P A 2
O23 O 0.0178(16) 0.7281(17) 0.4413(10) 0.036(3) Uani 0.28(2) 1 d D . P A 2
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N3 95.37(3) 3_666 . ?
N2 Cu1 N4 171.91(3) 3_666 . ?
N2 Cu1 N1 80.84(3) 3_666 3_666 ?
N2 Cu1 N5 93.86(4) 3_666 . ?
N2 Cu1 N5B 90.4(6) 3_666 . ?
N3 Cu1 N4 81.42(3) . . ?
N3 Cu1 N1 169.52(3) . 3_666 ?
N3 Cu1 N5 99.69(3) . . ?
N3 Cu1 N5B 92.7(6) . . ?
N4 Cu1 N1 103.56(3) . 3_666 ?
N4 Cu1 N5 79.45(4) . . ?
N4 Cu1 N5B 82.4(6) . . ?
N1 Cu1 N5 90.34(3) 3_666 . ?
N1 Cu1 N5B 97.1(6) 3_666 . ?
O11 Cl1 O12 106.3(3) . . ?
O14 Cl1 O11 107.5(3) . . ?
O14 Cl1 O12 107.9(3) . . ?
O13 Cl1 O11 114.0(4) . . ?
O13 Cl1 O12 110.9(4) . . ?
O13 Cl1 O14 109.9(3) . . ?
N3 N2 Cu1 131.94(5) . 3_666 ?
C2 N2 Cu1 119.25(5) . 3_666 ?
C2 N2 N3 108.76(6) . . ?
N2 N3 Cu1 132.68(5) . . ?
C4 N3 Cu1 118.65(5) . . ?
C4 N3 N2 108.59(6) . . ?
C11 N6 C10 114.47(9) . . ?
C11 N6 C10B 121.7(10) . . ?
C5 N4 Cu1 110.11(5) . . ?
C6 N4 Cu1 110.27(5) . . ?
C6 N4 C5 113.18(7) . . ?
N4 C5 C4 110.60(6) . . ?
N5 C8 C9 111.41(8) . . ?
N4 C6 C7 111.91(7) . . ?
C2 C3 C4 103.97(7) . . ?
N6 C10 C9 111.68(9) . . ?
C8 C9 C10 114.34(9) . . ?
N1 C1 C2 110.03(6) . . ?
N1 C12 C11 112.17(7) . . ?
N3 C4 C5 116.32(7) . . ?
N3 C4 C3 109.34(7) . . ?
C3 C4 C5 134.28(7) . . ?
N2 C2 C3 109.34(7) . . ?
N2 C2 C1 116.10(7) . . ?
C3 C2 C1 134.45(7) . . ?
N5 C7 C6 108.00(8) . . ?
N5B C7 C6 120.7(8) . . ?
N6 C11 C12 109.33(7) . . ?
C1 N1 Cu1 109.00(5) . 3_666 ?
C12 N1 Cu1 112.12(5) . 3_666 ?
C12 N1 C1 112.91(7) . . ?
C8 N5 Cu1 118.61(8) . . ?
C8 N5 C7 114.89(10) . . ?
C7 N5 Cu1 101.09(7) . . ?
C10B C9B C8B 114.9(14) . . ?
C9B C8B N5B 111.6(17) . . ?
C9B C10B N6 116(2) . . ?
C7 N5B Cu1 94.5(13) . . ?
C8B N5B Cu1 108.0(14) . . ?
C8B N5B C7 109.7(17) . . ?
O24 Cl2 O21 111.2(9) . . ?
O22 Cl2 O21 112.0(10) . . ?
O22 Cl2 O24 104.8(11) . . ?
O22 Cl2 O23 115.2(12) . . ?
O23 Cl2 O21 107.4(10) . . ?
O23 Cl2 O24 106.2(10) . . ?
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 1.9423(6) 3_666 ?
Cu1 N3 1.9519(6) . ?
Cu1 N4 2.0991(7) . ?
Cu1 N1 2.1278(7) 3_666 ?
Cu1 N5 2.4365(13) . ?
Cu1 N5B 2.57(3) . ?
Cl1 O11 1.448(5) . ?
Cl1 O12 1.471(3) . ?
Cl1 O14 1.447(4) . ?
Cl1 O13 1.409(4) . ?
N2 N3 1.3455(9) . ?
N2 C2 1.3383(10) . ?
N3 C4 1.3382(10) . ?
N6 C10 1.4700(16) . ?
N6 C11 1.4625(12) . ?
N6 C10B 1.60(2) . ?
N4 C5 1.4914(11) . ?
N4 C6 1.4852(11) . ?
C5 C4 1.4947(11) . ?
C8 C9 1.5238(13) . ?
C8 N5 1.4693(14) . ?
C6 C7 1.5145(13) . ?
C3 C4 1.3996(11) . ?
C3 C2 1.3960(11) . ?
C10 C9 1.5238(16) . ?
C1 C2 1.4974(11) . ?
C1 N1 1.4926(11) . ?
C12 C11 1.5192(13) . ?
C12 N1 1.4845(11) . ?
C7 N5 1.4697(16) . ?
C7 N5B 1.50(3) . ?
C9B C8B 1.455(15) . ?
C9B C10B 1.43(3) . ?
C8B N5B 1.46(3) . ?
Cl2 O21 1.415(10) . ?
Cl2 O24 1.411(11) . ?
Cl2 O22 1.386(13) . ?
Cl2 O23 1.412(11) . ?
