New complexes constructed from in situ nitration of (1H-tetrazol-5-yl)phenol: synthesis, structures and properties
Du, Ceng-Ceng; Wang, Xin-Fang; Zhou, Sheng-Bin; Wang, Duo-Zhi; Jia, Dianzeng; CrystEngComm  (2017) –; doi:10.1039/C7CE00753A

data_7229380
_publ_section_title
;
 New complexes constructed from in situ nitration of
 (1H-tetrazol-5-yl)phenol: synthesis, structures and properties
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00753A
_journal_year                    2017
_chemical_formula_moiety         'C56 H52.2 Cu7 N48 O57.1'
_chemical_formula_sum            'C56 H52.2 Cu7 N48 O57.1'
_chemical_formula_weight         2755.92
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-10-18 deposited with the CCDC.
2017-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                109.170(19)
_cell_angle_beta                 92.97(2)
_cell_angle_gamma                118.923(16)
_cell_formula_units_Z            1
_cell_length_a                   13.080(16)
_cell_length_b                   13.109(16)
_cell_length_c                   16.91(2)
_cell_measurement_reflns_used    621
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.46
_cell_measurement_theta_min      2.52
_cell_volume                     2318(5)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1256
_diffrn_reflns_av_unetI/netI     0.2709
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13000
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.318
_exptl_absorpt_coefficient_mu    1.698
_exptl_absorpt_correction_T_max  0.873
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_description       block
_exptl_crystal_F_000             1273
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_platon_squeeze_details
;
TITL 1 in P-1
CELL   13.0800   13.1100   16.9100    109.17     92.97    118.92
SPGR P-1
Q101 0.452 0.813 0.438 !       4.87 eA-3
Q102 0.127 0.453 0.267 !       3.62 eA-3
Q103 0.978 0.381 0.361 !       3.14 eA-3
C104 0.203 0.452 0.450 !       3.07 eA-3
Q105 0.689 0.979 0.136 !       2.95 eA-3
Q106 0.111 0.460 0.330 !       2.72 eA-3
C107 0.249 0.523 0.467 !       2.69 eA-3
C108 0.294 0.728 0.295 !       2.57 eA-3
Q109 0.846 0.834 0.176 !       2.52 eA-3
C110 0.760 0.286 0.453 !       2.46 eA-3
Q111 0.500 1.000 0.500 !       2.23 eA-3
C112 0.313 0.691 0.263 !       2.22 eA-3
C113 0.368 0.701 0.421 !       2.20 eA-3
Q114 0.312 0.793 0.279 !       2.13 eA-3
Q115 0.030 0.370 0.310 !       2.07 eA-3
C116 0.254 0.643 0.266 !       2.03 eA-3
C117 0.740 0.223 0.423 !       2.01 eA-3
Q118 0.497 0.763 0.407 !       2.00 eA-3
Q119 0.830 0.304 0.499 !       1.99 eA-3
Q120 0.900 0.378 0.051 !       1.97 eA-3
C121 0.283 0.687 0.452 !       1.85 eA-3
C122 0.251 0.729 0.230 !       1.84 eA-3
C123 0.426 0.750 0.376 !       1.82 eA-3
Q124 0.297 0.595 0.373 !       1.82 eA-3
Q125 0.030 0.459 0.426 !       1.82 eA-3
C126 0.268 0.674 0.229 !       1.80 eA-3
C127 0.238 0.594 0.447 !       1.80 eA-3
Q128 0.035 0.438 0.278 !       1.78 eA-3
C129 0.329 0.691 0.328 !       1.75 eA-3
Q130 0.154 0.562 0.243 !       1.70 eA-3
Q131 0.864 0.942 0.030 !       1.65 eA-3
Q132 0.792 1.000 0.077 !       1.64 eA-3
Q133 0.906 0.046 0.081 !       1.61 eA-3
Q134 0.620 0.084 0.316 !       1.58 eA-3
Q135 0.208 0.678 0.403 !       1.57 eA-3
Q136 0.190 0.790 0.077 !       1.56 eA-3
C137 0.073 0.374 0.376 !       1.56 eA-3
Q138 0.934 0.425 0.391 !       1.55 eA-3
Q139 1.001 0.245 0.341 !       1.55 eA-3
C140 0.265 0.654 0.380 !       1.53 eA-3
Q141 0.108 0.565 0.459 !       1.52 eA-3
Q142 0.062 0.450 0.364 !       1.52 eA-3
C143 0.829 0.366 0.463 !       1.52 eA-3
C144 0.144 0.484 0.422 !       1.51 eA-3
Q145 0.515 0.061 0.452 !       1.50 eA-3
Q146 0.155 0.705 0.015 !       1.50 eA-3
Q147 0.659 0.165 0.378 !       1.50 eA-3
Q148 0.220 0.741 0.324 !       1.49 eA-3
Q149 0.811 0.951 0.340 !       1.49 eA-3
Q150 0.267 0.729 0.372 !       1.48 eA-3
Q151 0.062 0.188 0.402 !       1.47 eA-3
Q152 0.361 0.542 0.236 !       1.46 eA-3
Q153 0.218 0.615 0.373 !       1.45 eA-3
Q154 0.844 0.894 0.078 !       1.45 eA-3
Q155 0.078 0.466 0.470 !       1.45 eA-3
Q156 0.826 0.125 0.078 !       1.45 eA-3
Q157 0.779 0.106 0.142 !       1.44 eA-3
Q158 0.922 0.350 0.110 !       1.44 eA-3
Q159 0.359 0.756 0.235 !       1.43 eA-3
Q160 0.686 0.186 0.461 !       1.43 eA-3
Q161 0.877 0.656 0.093 !       1.43 eA-3
Q162 0.470 0.522 0.392 !       1.43 eA-3
Q163 0.815 0.962 0.439 !       1.41 eA-3
Q164 0.075 0.276 0.438 !       1.37 eA-3
Q165 0.059 0.298 0.392 !       1.37 eA-3
Q166 0.034 0.148 0.015 !       1.36 eA-3
Q167 0.130 0.686 0.435 !       1.35 eA-3
Q168 0.341 0.834 0.345 !       1.35 eA-3
Q169 0.018 0.416 0.144 !       1.34 eA-3
C170 0.311 0.691 0.391 !       1.34 eA-3
Q171 0.956 0.360 0.424 !       1.33 eA-3
Q172 0.204 0.374 0.450 !       1.33 eA-3
Q173 0.097 0.503 0.104 !       1.33 eA-3
C174 0.096 0.464 0.407 !       1.31 eA-3
Q175 0.423 0.713 0.295 !       1.31 eA-3
Q176 0.238 0.637 0.173 !       1.30 eA-3
Q177 0.232 0.556 0.207 !       1.30 eA-3
Q178 0.267 0.924 0.088 !       1.30 eA-3
Q179 0.313 0.772 0.434 !       1.30 eA-3
Q180 0.433 0.667 0.388 !       1.29 eA-3
Q181 0.063 0.229 0.315 !       1.29 eA-3
Q182 0.168 0.992 0.033 !       1.29 eA-3
C183 0.721 0.361 0.462 !       1.29 eA-3
Q184 0.568 0.903 0.123 !       1.29 eA-3
Q185 0.670 0.104 0.391 !       1.28 eA-3
Q186 0.105 0.009 0.092 !       1.28 eA-3
C187 0.237 0.604 0.401 !       1.28 eA-3
Q188 0.065 0.320 0.215 !       1.27 eA-3
Q189 0.968 0.880 0.125 !       1.27 eA-3
Q190 0.388 0.808 0.252 !       1.26 eA-3
Q191 0.253 0.993 0.060 !       1.26 eA-3
Q192 0.889 0.223 0.330 !       1.26 eA-3
Q193 1.000 0.632 0.027 !       1.26 eA-3
Q194 0.247 0.751 0.047 !       1.26 eA-3
Q195 0.831 0.506 0.191 !       1.25 eA-3
Q196 0.950 0.500 0.460 !       1.25 eA-3
Q197 0.641 0.227 0.160 !       1.25 eA-3
Q198 0.640 0.018 0.437 !       1.25 eA-3
Q199 0.370 0.782 0.329 !       1.24 eA-3
;
_refine_diff_density_max         1.850
_refine_diff_density_min         -1.686
_refine_diff_density_rms         0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     751
_refine_ls_number_reflns         8107
_refine_ls_number_restraints     203
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.2352
_refine_ls_R_factor_gt           0.0740
_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/[\s^2^(Fo^2^)+(0.1591P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2480
_refine_ls_wR_factor_ref         0.3221
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3147
_reflns_number_total             8107
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce00753a2.cif
_cod_data_source_block           5
_cod_database_code               7229380
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.876
_shelx_estimated_absorpt_t_min   0.822
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 N12-O12A = N12-O13A = N12-O12B = N12-O13B
 1.22 with sigma of 0.02
 N1-O1A = N1-O1B = N1-O2A = N1-O2B
 1.22 with sigma of 0.02
 O1A-O2A \\sim O1B-O2B \\sim O12A-O13A \\sim O12B-O13B
 with sigma of 0.01
 C11-O12A \\sim C11-O12B \\sim C11-O13A \\sim C11-O13B
 with sigma of 0.01
 C2-O2A \\sim C2-O1A \\sim C2-O1B \\sim C2-O2B
 with sigma of 0.01
3. Rigid bond restraints
 Cu3, N16, Cu4, O10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N2, O4, O5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C2, N1, O1A, O1B, O2A, O2B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C11, N12, O12A, O12B, O13A, O13B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
C2 \\sim N1 \\sim O1A \\sim O1B \\sim O2A \\sim O2B: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
C11 \\sim N12 \\sim O12A \\sim O12B \\sim O13A \\sim O13B: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(O16) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(N16) \\sim Ueq, Uanis(N11) \\sim Ueq, Uanis(N15) \\sim Ueq:
with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Others
 Sof(O1B)=Sof(O2B)=1-FVAR(1)
 Sof(O1A)=Sof(O2A)=FVAR(1)
 Sof(O12B)=Sof(O13B)=1-FVAR(2)
 Sof(O12A)=Sof(O13A)=FVAR(2)
6.a Rotating group:
 O6(H6A,H6B), O8(H8A,H8B)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C10(H10), C14(H14), C17(H17), C21(H21), C24(H24), C28(H28),
 N19(H19)
6.c Idealised tetrahedral OH refined as rotating group:
 O3(H3A), O21(H21A)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'