#------------------------------------------------------------------------------
#$Date: 2020-06-05 13:55:49 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252815 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/40/7704065.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_7704065
loop_
_publ_author_name
'Lippi, Martina'
'Caputo, Josefina'
'Famulari, Antonino'
'Sacchetti, Alessandro'
'Castellano, Carlo'
'Meneghetti, Fiorella'
'Martí-Rujas, Javier'
'Cametti, Massimo'
_publ_section_title
;
 Combined structural and theoretical investigation on differently
 substituted bispidine ligands: predicting the properties of their
 corresponding coordination polymers.
;
_journal_issue                   18
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5965
_journal_page_last               5973
_journal_paper_doi               10.1039/d0dt00799d
_journal_volume                  49
_journal_year                    2020
_chemical_formula_sum            'C25 H30 N4 O5'
_chemical_formula_weight         466.53
_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   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-06-07 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.41(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.548(3)
_cell_length_b                   11.382(2)
_cell_length_c                   14.751(3)
_cell_measurement_reflns_used    9854
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      31.35
_cell_measurement_theta_min      2.24
_cell_volume                     2376.0(9)
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker APEX II CCD diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24216
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.529
_diffrn_reflns_theta_min         1.439
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.699
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         7403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0591
_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)+(0.0701P)²+1.0163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1473
_refine_ls_wR_factor_ref         0.1638
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5771
_reflns_number_total             7403
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt00799d2.cif
_cod_data_source_block           JC3_L2
_cod_depositor_comments
'Adding full bibliography for 7704064--7704069.cif.'
_cod_original_cell_volume        2375.8(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7704065
_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.
;
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
C1 C 0.64753(9) -0.03827(11) 1.13513(9) 0.0299(2) Uani 1 1 d . . . . .
C2 C 0.65548(9) 0.08840(11) 1.10525(9) 0.0289(2) Uani 1 1 d . . . . .
C3 C 0.74065(10) 0.14051(13) 1.17646(9) 0.0344(3) Uani 1 1 d . . . . .
C4 C 0.81731(10) -0.04624(13) 1.19957(10) 0.0362(3) Uani 1 1 d . . . . .
C5 C 0.73554(9) -0.10590(11) 1.12832(9) 0.0293(2) Uani 1 1 d . . . . .
C6 C 0.74264(9) -0.10529(11) 1.02378(9) 0.0272(2) Uani 1 1 d . . . . .
C7 C 0.66334(9) 0.08836(10) 1.00113(8) 0.0271(2) Uani 1 1 d . . . . .
C8 C 0.72831(11) -0.23261(13) 1.16100(10) 0.0385(3) Uani 1 1 d . . . . .
C9 C 0.56348(10) 0.15253(12) 1.10723(10) 0.0358(3) Uani 1 1 d . . . . .
C10 C 0.6575(2) -0.41736(17) 1.12407(18) 0.0660(6) Uani 1 1 d . . . . .
C11 C 0.4915(2) 0.3051(3) 1.1717(2) 0.0799(8) Uani 1 1 d . . . . .
C12 C 0.90618(12) 0.13056(16) 1.25224(12) 0.0473(4) Uani 1 1 d . . . . .
C13 C 0.99878(17) 0.0673(3) 1.2609(3) 0.0917(10) Uani 1 1 d . . . . .
C14 C 0.91947(19) 0.2597(2) 1.23226(19) 0.0727(7) Uani 1 1 d . . . . .
C18 C 0.73119(14) 0.00474(15) 0.88379(10) 0.0430(3) Uani 1 1 d . . . . .
C19 C 0.67565(9) 0.21348(11) 0.97012(9) 0.0310(3) Uani 1 1 d . . . . .
C20 C 0.59983(12) 0.27783(14) 0.92036(12) 0.0426(3) Uani 1 1 d . . . . .
C21 C 0.61540(15) 0.39192(16) 0.89454(15) 0.0553(4) Uani 1 1 d . . . . .
C22 C 0.77050(14) 0.38264(15) 0.96327(14) 0.0510(4) Uani 1 1 d . . . . .
C23 C 0.76357(11) 0.26762(13) 0.99089(11) 0.0390(3) Uani 1 1 d . . . . .
C24 C 0.83158(9) -0.16827(11) 1.01300(9) 0.0300(2) Uani 1 1 d . . . . .
C25 C 0.82844(11) -0.28164(13) 0.97853(12) 0.0400(3) Uani 1 1 d . . . . .
C26 C 0.91176(13) -0.33450(15) 0.96942(14) 0.0511(4) Uani 1 1 d . . . . .
C27 C 0.99820(11) -0.17411(16) 1.02501(14) 0.0487(4) Uani 1 1 d . . . . .
C28 C 0.91921(10) -0.11332(14) 1.03575(11) 0.0395(3) Uani 1 1 d . . . . .
N1 N 0.82914(8) 0.07767(11) 1.17898(8) 0.0347(2) Uani 1 1 d . . . . .
N2 N 0.74113(8) 0.01445(9) 0.98519(7) 0.0288(2) Uani 1 1 d . . . . .
N3 N 0.69841(13) 0.44600(13) 0.91576(12) 0.0587(4) Uani 1 1 d . . . . .
N4 N 0.99629(11) -0.28365(14) 0.99251(12) 0.0532(4) Uani 1 1 d . . . . .
O1 O 0.58493(8) -0.07627(10) 1.16759(9) 0.0464(3) Uani 1 1 d . . . . .
O2 O 0.48873(8) 0.12803(12) 1.05760(11) 0.0554(3) Uani 1 1 d . . . . .
O3 O 0.57632(9) 0.24048(12) 1.16814(9) 0.0562(3) Uani 1 1 d . . . . .
O4 O 0.77291(13) -0.27080(13) 1.23275(11) 0.0783(5) Uani 1 1 d . . . . .
O5 O 0.66660(9) -0.29585(10) 1.09965(8) 0.0476(3) Uani 1 1 d . . . . .
H6 H 0.6880(11) -0.1492(14) 0.9894(11) 0.027(4) Uiso 1 1 d . . . . .
H7 H 0.6017(11) 0.0606(14) 0.9655(11) 0.027(4) Uiso 1 1 d . . . . .
H20 H 0.5371(14) 0.2440(18) 0.9028(14) 0.052(5) Uiso 1 1 d . . . . .
H21 H 0.5637(18) 0.437(2) 0.8578(18) 0.078(7) Uiso 1 1 d . . . . .
H22 H 0.8337(16) 0.421(2) 0.9814(16) 0.064(6) Uiso 1 1 d . . . . .
H23 H 0.8179(13) 0.2264(17) 1.0245(13) 0.044(5) Uiso 1 1 d . . . . .
H25 H 0.7682(14) -0.3210(18) 0.9590(14) 0.050(5) Uiso 1 1 d . . . . .
H26 H 0.9093(17) -0.410(2) 0.9411(17) 0.070(7) Uiso 1 1 d . . . . .
H27 H 1.0605(16) -0.136(2) 1.0445(16) 0.066(6) Uiso 1 1 d . . . . .
H28 H 0.9250(13) -0.0341(17) 1.0585(13) 0.043(5) Uiso 1 1 d . . . . .
H31 H 0.7475(12) 0.2226(16) 1.1590(12) 0.036(4) Uiso 1 1 d . . . . .
H32 H 0.7238(13) 0.1374(16) 1.2377(13) 0.044(5) Uiso 1 1 d . . . . .
H41 H 0.8738(13) -0.0908(16) 1.1988(13) 0.044(5) Uiso 1 1 d . . . . .
H42 H 0.8031(12) -0.0578(16) 1.2615(13) 0.041(4) Uiso 1 1 d . . . . .
H181 H 0.6698(17) -0.031(2) 0.8536(17) 0.068(6) Uiso 1 1 d . . . . .
H182 H 0.7317(15) 0.0790(19) 0.8553(15) 0.057(6) Uiso 1 1 d . . . . .
H183 H 0.7820(15) -0.042(2) 0.8693(15) 0.058(6) Uiso 1 1 d . . . . .
H200 H 0.8875(14) 0.1239(19) 1.3145(15) 0.057(6) Uiso 1 1 d . . . . .
H100 H 0.612(2) -0.450(3) 1.070(2) 0.102(10) Uiso 1 1 d . . . . .
H101 H 0.635(2) -0.422(3) 1.182(2) 0.097(9) Uiso 1 1 d . . . . .
H110 H 0.449(2) 0.253(3) 1.188(2) 0.091(10) Uiso 1 1 d . . . . .
H112 H 0.514(2) 0.365(3) 1.218(2) 0.104(10) Uiso 1 1 d . . . . .
H111 H 0.459(2) 0.335(3) 1.111(2) 0.095(9) Uiso 1 1 d . . . . .
H102 H 0.716(2) -0.452(3) 1.135(2) 0.111(12) Uiso 1 1 d . . . . .
H133 H 1.049(2) 0.112(3) 1.307(2) 0.102(9) Uiso 1 1 d . . . . .
H131 H 1.016(2) 0.065(3) 1.198(3) 0.109(11) Uiso 1 1 d . . . . .
H143 H 0.977(2) 0.290(2) 1.279(2) 0.088(8) Uiso 1 1 d . . . . .
H141 H 0.934(2) 0.270(3) 1.167(3) 0.127(12) Uiso 1 1 d . . . . .
H132 H 1.001(3) -0.015(4) 1.283(3) 0.129(14) Uiso 1 1 d . . . . .
H142 H 0.860(3) 0.312(3) 1.240(2) 0.122(12) Uiso 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'
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
O1 C1 C5 124.90(12) . . ?
O1 C1 C2 124.88(12) . . ?
C5 C1 C2 109.88(10) . . ?
C1 C2 C9 108.73(10) . . ?
C1 C2 C3 105.67(11) . . ?
C9 C2 C3 111.77(11) . . ?
C1 C2 C7 108.17(10) . . ?
C9 C2 C7 106.37(11) . . ?
C3 C2 C7 115.94(10) . . ?
N1 C3 C2 113.03(11) . . ?
N1 C4 C5 113.00(11) . . ?
C1 C5 C8 109.65(11) . . ?
C1 C5 C4 105.06(11) . . ?
C8 C5 C4 107.28(11) . . ?
C1 C5 C6 108.16(10) . . ?
C8 C5 C6 109.77(10) . . ?
C4 C5 C6 116.71(11) . . ?
N2 C6 C24 109.40(10) . . ?
N2 C6 C5 112.63(10) . . ?
C24 C6 C5 110.64(10) . . ?
N2 C7 C19 109.81(10) . . ?
N2 C7 C2 112.98(10) . . ?
C19 C7 C2 109.60(10) . . ?
O4 C8 O5 123.47(15) . . ?
O4 C8 C5 124.17(15) . . ?
O5 C8 C5 112.36(12) . . ?
O2 C9 O3 123.74(14) . . ?
O2 C9 C2 123.55(13) . . ?
O3 C9 C2 112.68(13) . . ?
N1 C12 C13 112.06(16) . . ?
N1 C12 C14 110.96(15) . . ?
C13 C12 C14 109.1(2) . . ?
C20 C19 C23 117.52(13) . . ?
C20 C19 C7 121.37(12) . . ?
C23 C19 C7 121.10(12) . . ?
C19 C20 C21 118.70(16) . . ?
N3 C21 C20 124.58(17) . . ?
N3 C22 C23 124.50(17) . . ?
C22 C23 C19 118.81(15) . . ?
C25 C24 C28 117.30(13) . . ?
C25 C24 C6 121.47(12) . . ?
C28 C24 C6 121.21(12) . . ?
C24 C25 C26 119.01(14) . . ?
N4 C26 C25 124.28(16) . . ?
N4 C27 C28 124.11(15) . . ?
C27 C28 C24 119.20(14) . . ?
C4 N1 C3 109.34(11) . . ?
C4 N1 C12 110.11(12) . . ?
C3 N1 C12 109.24(12) . . ?
C7 N2 C18 107.88(11) . . ?
C7 N2 C6 114.17(9) . . ?
C18 N2 C6 108.16(11) . . ?
C21 N3 C22 115.84(15) . . ?
C26 N4 C27 116.09(14) . . ?
C9 O3 C11 114.83(18) . . ?
C8 O5 C10 115.82(16) . . ?
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
C1 O1 1.2034(16) . ?
C1 C5 1.5170(18) . ?
C1 C2 1.5198(18) . ?
C2 C9 1.5307(18) . ?
C2 C3 1.5449(19) . ?
C2 C7 1.5664(17) . ?
C3 N1 1.4655(18) . ?
C4 N1 1.4613(19) . ?
C4 C5 1.5495(19) . ?
C5 C8 1.5319(19) . ?
C5 C6 1.5694(17) . ?
C6 N2 1.4752(16) . ?
C6 C24 1.5194(17) . ?
C7 N2 1.4721(16) . ?
C7 C19 1.5190(17) . ?
C8 O4 1.188(2) . ?
C8 O5 1.329(2) . ?
C9 O2 1.194(2) . ?
C9 O3 1.3291(18) . ?
C10 O5 1.443(2) . ?
C11 O3 1.448(2) . ?
C12 N1 1.4915(19) . ?
C12 C13 1.506(3) . ?
C12 C14 1.520(3) . ?
C18 N2 1.4731(17) . ?
C19 C20 1.384(2) . ?
C19 C23 1.388(2) . ?
C20 C21 1.387(2) . ?
C21 N3 1.327(3) . ?
C22 N3 1.331(3) . ?
C22 C23 1.382(2) . ?
C24 C25 1.3838(19) . ?
C24 C28 1.3894(19) . ?
C25 C26 1.387(2) . ?
C26 N4 1.330(2) . ?
C27 N4 1.334(2) . ?
C27 C28 1.382(2) . ?
