#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:14:38 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230422 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/70/7057015.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_7057015
loop_
_publ_author_name
'Berezin, A. S.'
'Ivanova, A. D.'
'Komarov, V. Yu.'
'Nadolinny, V. A.'
'Lavrenova, L. G.'
_publ_section_title
;
 Influence of water on the structure and magnetic properties of a copper
 bromide coordination compound with 3-amino-4-ethoxycarbonylpyrazole
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              4902
_journal_paper_doi               10.1039/C8NJ00017D
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         '(C24 H36 Br2 Cu N12 O8), 2(H2O)'
_chemical_formula_sum            'C24 H40 Br2 Cu N12 O10'
_chemical_formula_weight         880.04
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-12-07 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                103.046(8)
_cell_angle_beta                 106.647(9)
_cell_angle_gamma                94.822(8)
_cell_formula_units_Z            1
_cell_length_a                   7.5931(19)
_cell_length_b                   9.5094(19)
_cell_length_c                   13.177(3)
_cell_measurement_reflns_used    997
_cell_measurement_temperature    200
_cell_measurement_theta_max      20.83
_cell_measurement_theta_min      2.80
_cell_volume                     876.7(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_unetI/netI     0.1200
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8450
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.227
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.970
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0696 before and 0.0588 after correction. The Ratio of minimum to maximum transmission is 0.8571. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            'greenish yellow'
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_description       plank
_exptl_crystal_F_000             447
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0480
_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)+(0.0238P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0885
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1918
_reflns_number_total             3083
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj00017d2.cif
_cod_data_source_block           structure4
_cod_depositor_comments
'Adding full bibliography for 7057015--7057017.cif.'
_cod_database_code               7057015
_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_max   0.985
_shelx_estimated_absorpt_t_min   0.756
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 N12(H12), C11(H11), N22(H22), C21(H21)
2.c X=CH2 refined with riding coordinates:
 N13(H13A,H13B), N23(H23A,H23B)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Br1 Br 0.17123(8) 0.33578(6) 1.02405(5) 0.02962(19) Uani 1 1 d . . .
Cu1 Cu 0.5000 0.5000 1.0000 0.0237(3) Uani 1 2 d S T P
O11 O 0.0427(6) 0.6853(4) 0.5581(3) 0.0461(12) Uani 1 1 d . . .
O12 O 0.3431(5) 0.6553(4) 0.5788(3) 0.0354(10) Uani 1 1 d . . .
N11 N 0.3326(6) 0.5315(4) 0.8606(4) 0.0218(11) Uani 1 1 d . . .
N12 N 0.1512(6) 0.5518(4) 0.8487(4) 0.0275(12) Uani 1 1 d . . .
H12 H 0.0935 0.5400 0.8960 0.033 Uiso 1 1 calc R . .
N13 N -0.1048(6) 0.6160(5) 0.7247(4) 0.0420(14) Uani 1 1 d . . .
H13A H -0.1767 0.6058 0.7652 0.050 Uiso 1 1 calc R . .
H13B H -0.1487 0.6419 0.6633 0.050 Uiso 1 1 calc R . .
C11 C 0.3640(7) 0.5587(5) 0.7727(4) 0.0234(13) Uani 1 1 d . . .
H11 H 0.4791 0.5533 0.7581 0.028 Uiso 1 1 calc R . .
C12 C 0.2081(7) 0.5964(5) 0.7037(4) 0.0218(13) Uani 1 1 d . . .
C13 C 0.0722(8) 0.5918(5) 0.7564(5) 0.0250(13) Uani 1 1 d . . .
C14 C 0.1831(9) 0.6476(6) 0.6057(5) 0.0309(15) Uani 1 1 d . . .
C15 C 0.3343(9) 0.7178(7) 0.4866(5) 0.0477(18) Uani 1 1 d . . .
H15A H 0.2289 0.6629 0.4217 0.057 Uiso 1 1 calc R . .
H15B H 0.3155 0.8211 0.5054 0.057 Uiso 1 1 calc R . .
C16 C 0.5084(9) 0.7087(8) 0.4625(5) 0.067(2) Uani 1 1 d . . .
H16A H 0.5057 0.7503 0.4005 0.101 Uiso 1 1 calc GR . .
H16B H 0.5253 0.6061 0.4436 0.101 Uiso 1 1 calc GR . .
H16C H 0.6117 0.7637 0.5270 0.101 Uiso 1 1 calc GR . .
O21 O 0.7513(6) -0.0886(4) 0.7441(4) 0.0542(14) Uani 1 1 d . . .
O22 O 0.8740(5) 0.1232(3) 0.7260(3) 0.0320(10) Uani 1 1 d . . .
N21 N 0.5524(6) 0.3118(4) 0.9140(4) 0.0235(11) Uani 1 1 d . . .
N22 N 0.4645(6) 0.1801(4) 0.9146(4) 0.0245(11) Uani 1 1 d . . .
H22 H 0.3793 0.1702 0.9469 0.029 Uiso 1 1 calc R . .
N23 N 0.4586(6) -0.0718(4) 0.8473(4) 0.0441(15) Uani 1 1 d . . .
H23A H 0.3717 -0.0929 0.8760 0.053 Uiso 1 1 calc R . .
H23B H 0.5017 -0.1426 0.8106 0.053 Uiso 1 1 calc R . .
C21 C 0.6678(7) 0.2794(5) 0.8575(4) 0.0237(13) Uani 1 1 d . . .
H21 H 0.7487 0.3498 0.8441 0.028 Uiso 1 1 calc R . .
C22 C 0.6561(7) 0.1274(5) 0.8197(4) 0.0200(13) Uani 1 1 d . . .
C23 C 0.5254(7) 0.0680(5) 0.8594(4) 0.0225(13) Uani 1 1 d . . .
C24 C 0.7616(8) 0.0423(6) 0.7591(5) 0.0276(14) Uani 1 1 d . . .
C25 C 0.9959(8) 0.0454(6) 0.6742(5) 0.0427(17) Uani 1 1 d . . .
H25A H 0.9217 -0.0213 0.6023 0.051 Uiso 1 1 calc R . .
H25B H 1.0632 -0.0134 0.7211 0.051 Uiso 1 1 calc R . .
C26 C 1.1319(8) 0.1562(6) 0.6587(5) 0.0424(17) Uani 1 1 d . . .
H26A H 1.0646 0.2093 0.6082 0.064 Uiso 1 1 calc GR . .
H26B H 1.2204 0.1063 0.6282 0.064 Uiso 1 1 calc GR . .
H26C H 1.1995 0.2252 0.7297 0.064 Uiso 1 1 calc GR . .
O1 O 0.1318(6) -0.0754(5) 0.9262(4) 0.0591(13) Uani 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'
Br Br -0.2901 2.4595 '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
N11 Cu1 N11 180.0(2) . 2_667
N11 Cu1 N21 89.58(16) 2_667 .
N11 Cu1 N21 90.42(16) 2_667 2_667
N11 Cu1 N21 90.42(17) . .
N11 Cu1 N21 89.58(16) . 2_667
N21 Cu1 N21 180.0 . 2_667
C14 O12 C15 114.4(4) . .
N12 N11 Cu1 121.8(3) . .
C11 N11 Cu1 132.9(4) . .
C11 N11 N12 104.6(4) . .
N11 N12 H12 123.8 . .
C13 N12 N11 112.3(4) . .
C13 N12 H12 123.8 . .
H13A N13 H13B 120.0 . .
C13 N13 H13A 120.0 . .
C13 N13 H13B 120.0 . .
N11 C11 H11 123.9 . .
N11 C11 C12 112.2(4) . .
C12 C11 H11 123.9 . .
C11 C12 C13 104.8(5) . .
C11 C12 C14 131.6(5) . .
C13 C12 C14 123.2(5) . .
N12 C13 C12 106.1(5) . .
N13 C13 N12 124.2(5) . .
N13 C13 C12 129.7(5) . .
O11 C14 O12 124.6(5) . .
O11 C14 C12 124.4(5) . .
O12 C14 C12 110.9(5) . .
O12 C15 H15A 110.1 . .
O12 C15 H15B 110.1 . .
H15A C15 H15B 108.4 . .
C16 C15 O12 108.0(5) . .
C16 C15 H15A 110.1 . .
C16 C15 H15B 110.1 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C24 O22 C25 115.8(4) . .
N22 N21 Cu1 119.6(3) . .
C21 N21 Cu1 134.7(3) . .
C21 N21 N22 105.6(4) . .
N21 N22 H22 124.4 . .
C23 N22 N21 111.2(4) . .
C23 N22 H22 124.4 . .
H23A N23 H23B 120.0 . .
C23 N23 H23A 120.0 . .
C23 N23 H23B 120.0 . .
N21 C21 H21 124.4 . .
N21 C21 C22 111.3(4) . .
C22 C21 H21 124.4 . .
C21 C22 C24 130.6(4) . .
C23 C22 C21 104.9(4) . .
C23 C22 C24 124.4(4) . .
N22 C23 C22 107.1(4) . .
N23 C23 N22 122.4(4) . .
N23 C23 C22 130.4(4) . .
O21 C24 O22 123.8(5) . .
O21 C24 C22 122.7(5) . .
O22 C24 C22 113.4(4) . .
O22 C25 H25A 110.1 . .
O22 C25 H25B 110.1 . .
O22 C25 C26 108.2(4) . .
H25A C25 H25B 108.4 . .
C26 C25 H25A 110.1 . .
C26 C25 H25B 110.1 . .
C25 C26 H26A 109.5 . .
C25 C26 H26B 109.5 . .
C25 C26 H26C 109.5 . .
H26A C26 H26B 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N11 2.014(4) .
Cu1 N11 2.014(4) 2_667
Cu1 N21 2.027(4) .
Cu1 N21 2.027(4) 2_667
O11 C14 1.200(6) .
O12 C14 1.360(6) .
O12 C15 1.457(6) .
N11 N12 1.376(5) .
N11 C11 1.322(6) .
N12 H12 0.8800 .
N12 C13 1.346(6) .
N13 H13A 0.8800 .
N13 H13B 0.8800 .
N13 C13 1.344(6) .
C11 H11 0.9500 .
C11 C12 1.399(7) .
C12 C13 1.403(7) .
C12 C14 1.448(7) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C15 C16 1.450(8) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
O21 C24 1.207(5) .
O22 C24 1.329(6) .
O22 C25 1.455(6) .
N21 N22 1.372(5) .
N21 C21 1.316(6) .
N22 H22 0.8800 .
N22 C23 1.343(6) .
N23 H23A 0.8800 .
N23 H23B 0.8800 .
N23 C23 1.340(6) .
C21 H21 0.9500 .
C21 C22 1.405(6) .
C22 C23 1.384(6) .
C22 C24 1.456(6) .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C25 C26 1.501(7) .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
