#------------------------------------------------------------------------------
#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/04/4120442.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_4120442
loop_
_publ_author_name
'Liu, Guangfeng'
'Liu, Jie'
'Liu, Yang'
'Tao, Xutang'
_publ_section_title
;
 Oriented Single-Crystal-to-Single-Crystal Phase Transition with Dramatic
 Changes in the Dimensions of Crystals.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              590
_journal_page_last               593
_journal_paper_doi               10.1021/ja4102634
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C18 H12 Cu N2 O2, C12 H4 N4'
_chemical_formula_sum            'C30 H16 Cu N6 O2'
_chemical_formula_weight         556.03
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.500(1)
_cell_angle_beta                 72.920(3)
_cell_angle_gamma                77.610(1)
_cell_formula_units_Z            1
_cell_length_a                   7.9345(4)
_cell_length_b                   8.2352(4)
_cell_length_c                   9.7232(4)
_cell_measurement_reflns_used    6083
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.22
_cell_volume                     585.11(5)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6858
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.977
_exptl_absorpt_correction_T_max  0.9347
_exptl_absorpt_correction_T_min  0.6434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 Software Suite (Bruker,2009)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             283
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2657
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0230
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0430P)²+0.3816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0671
_reflns_number_gt                2645
_reflns_number_total             2657
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4102634_si_002.cif
_cod_data_source_block           FormII100K
_cod_depositor_comments
;
The following automatic conversions were performed:
'__cell_measurement_reflns_used' tag replaced with
'_cell_measurement_reflns_used'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        585.09(5)
_cod_original_sg_symbol_Hall     '-P 1   '
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               4120442
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.0000 1.0000 0.0000 0.01207(8) Uani 1 2 d S
O1 O -0.07750(13) 0.90736(12) -0.13381(10) 0.01623(19) Uani 1 1 d .
N1 N 0.38866(18) 1.57596(16) -0.19750(15) 0.0258(3) Uani 1 1 d .
N2 N 0.30196(17) 1.20500(16) -0.42381(14) 0.0234(3) Uani 1 1 d .
N3 N -0.05805(14) 1.21646(14) -0.11961(12) 0.0131(2) Uani 1 1 d .
C1 C 0.39525(18) 1.43712(18) -0.20418(14) 0.0175(3) Uani 1 1 d .
C2 C 0.40085(17) 1.26367(17) -0.21138(14) 0.0155(2) Uani 1 1 d .
C3 C 0.44997(17) 1.13385(16) -0.10727(14) 0.0145(2) Uani 1 1 d .
C4 C 0.50275(17) 1.16697(17) 0.01248(14) 0.0157(2) Uani 1 1 d .
H4 H 0.5041 1.2776 0.0193 0.019 Uiso 1 1 calc R
C5 C 0.44962(17) 0.95977(17) -0.11501(14) 0.0154(2) Uani 1 1 d .
H5 H 0.4163 0.9352 -0.1913 0.019 Uiso 1 1 calc R
C6 C 0.34707(18) 1.23227(17) -0.33023(15) 0.0170(3) Uani 1 1 d .
C7 C -0.11662(16) 1.19657(16) -0.23187(14) 0.0125(2) Uani 1 1 d .
C8 C -0.16579(17) 1.33371(17) -0.33564(14) 0.0143(2) Uani 1 1 d .
C9 C -0.22390(18) 1.29971(17) -0.44931(14) 0.0164(3) Uani 1 1 d .
H9 H -0.2584 1.3873 -0.5188 0.020 Uiso 1 1 calc R
C10 C -0.22879(17) 1.13506(17) -0.45602(14) 0.0160(3) Uani 1 1 d .
H10 H -0.2645 1.1134 -0.5323 0.019 Uiso 1 1 calc R
C11 C -0.18163(17) 0.99883(17) -0.35135(14) 0.0156(2) Uani 1 1 d .
H11 H -0.1888 0.8899 -0.3587 0.019 Uiso 1 1 calc R
C12 C -0.12445(16) 1.02560(16) -0.23729(14) 0.0130(2) Uani 1 1 d .
C13 C -0.15195(19) 1.49588(17) -0.31667(15) 0.0177(3) Uani 1 1 d .
H13 H -0.1830 1.5904 -0.3819 0.021 Uiso 1 1 calc R
C14 C -0.0929(2) 1.51380(17) -0.20231(16) 0.0199(3) Uani 1 1 d .
H14 H -0.0836 1.6200 -0.1897 0.024 Uiso 1 1 calc R
C15 C -0.04653(18) 1.36978(17) -0.10447(15) 0.0168(3) Uani 1 1 d .
H15 H -0.0067 1.3823 -0.0270 0.020 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
O1 Cu1 O1 180.00(3) . 2_575
O1 Cu1 N3 84.65(4) . .
O1 Cu1 N3 95.35(4) 2_575 .
O1 Cu1 N3 95.35(4) . 2_575
O1 Cu1 N3 84.65(4) 2_575 2_575
N3 Cu1 N3 180.00(6) . 2_575
C12 O1 Cu1 111.67(8) . .
C15 N3 C7 119.67(11) . .
C15 N3 Cu1 129.15(9) . .
C7 N3 Cu1 111.17(8) . .
N1 C1 C2 179.18(16) . .
C3 C2 C6 121.48(12) . .
C3 C2 C1 122.08(12) . .
C6 C2 C1 116.41(12) . .
C2 C3 C4 121.02(12) . .
C2 C3 C5 120.93(12) . .
C4 C3 C5 118.05(12) . .
C5 C4 C3 121.23(12) 2_675 .
C5 C4 H4 119.4 2_675 .
C3 C4 H4 119.4 . .
C4 C5 C3 120.72(12) 2_675 .
C4 C5 H5 119.6 2_675 .
C3 C5 H5 119.6 . .
N2 C6 C2 178.72(15) . .
N3 C7 C8 122.52(12) . .
N3 C7 C12 114.93(11) . .
C8 C7 C12 122.55(12) . .
C7 C8 C9 118.22(12) . .
C7 C8 C13 116.51(12) . .
C9 C8 C13 125.27(12) . .
C10 C9 C8 119.30(12) . .
C10 C9 H9 120.4 . .
C8 C9 H9 120.4 . .
C9 C10 C11 122.30(12) . .
C9 C10 H10 118.9 . .
C11 C10 H10 118.9 . .
C12 C11 C10 120.62(12) . .
C12 C11 H11 119.7 . .
C10 C11 H11 119.7 . .
O1 C12 C11 125.46(12) . .
O1 C12 C7 117.54(11) . .
C11 C12 C7 116.99(11) . .
C14 C13 C8 120.22(12) . .
C14 C13 H13 119.9 . .
C8 C13 H13 119.9 . .
C13 C14 C15 119.26(12) . .
C13 C14 H14 120.4 . .
C15 C14 H14 120.4 . .
N3 C15 C14 121.81(12) . .
N3 C15 H15 119.1 . .
C14 C15 H15 119.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9375(9) .
Cu1 O1 1.9375(9) 2_575
Cu1 N3 1.9512(11) .
Cu1 N3 1.9512(11) 2_575
O1 C12 1.3190(16) .
N1 C1 1.148(2) .
N2 C6 1.1492(19) .
N3 C15 1.3275(17) .
N3 C7 1.3573(16) .
C1 C2 1.4358(19) .
C2 C3 1.3798(18) .
C2 C6 1.4321(18) .
C3 C4 1.4416(18) .
C3 C5 1.4524(18) .
C4 C5 1.3519(19) 2_675
C4 H4 0.9300 .
C5 C4 1.3519(19) 2_675
C5 H5 0.9300 .
C7 C8 1.4123(17) .
C7 C12 1.4355(17) .
C8 C9 1.4147(18) .
C8 C13 1.4181(18) .
C9 C10 1.3808(19) .
C9 H9 0.9300 .
C10 C11 1.4084(18) .
C10 H10 0.9300 .
C11 C12 1.3888(18) .
C11 H11 0.9300 .
C13 C14 1.3730(19) .
C13 H13 0.9300 .
C14 C15 1.4059(18) .
C14 H14 0.9300 .
C15 H15 0.9300 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139122414
