#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:30:04 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230509 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/77/7057747.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_7057747
loop_
_publ_author_name
'Biancalana, Lorenzo'
'Fulignati, Sara'
'Antonetti, Claudia'
'Zacchini, Stefano'
'Provinciali, Giacomo'
'Pampaloni, Guido'
'Raspolli Galletti, Anna Maria'
'Marchetti, Fabio'
_publ_section_title
;
 Ruthenium p-cymene complexes with α-diimine ligands as catalytic
 precursors for the transfer hydrogenation of ethyl levulinate to
 γ-valerolactone
;
_journal_issue                   21
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17574
_journal_paper_doi               10.1039/C8NJ03569E
_journal_volume                  42
_journal_year                    2018
_chemical_formula_sum            'C14 H12 N2 O2'
_chemical_formula_weight         240.26
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-03-16 deposited with the CCDC.
2018-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.589(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.9045(11)
_cell_length_b                   11.022(2)
_cell_length_c                   10.913(3)
_cell_measurement_reflns_used    2267
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5255
_cell_measurement_theta_min      2.654
_cell_volume                     577.9(2)
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6473
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.654
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6892
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1116 (selected reflections only, before parameter refinement)
 R(int) =  0.0499 (selected reflections only, after parameter refinement)
;
_exptl_crystal_colour            orange-brown
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       needle
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0439
_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/[σ²(Fo²)+(0.0416P)²+0.3406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1025
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1002
_reflns_number_total             1260
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj03569e2.cif
_cod_data_source_block           L2
_cod_depositor_comments
'Adding full bibliography for 7057747--7057748.cif.'
_cod_database_code               7057747
_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_min   0.982
_shelx_estimated_absorpt_t_max   0.987
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
C1 C 0.8934(3) 0.46008(14) 0.46609(14) 0.0137(3) Uani 1 1 d . .
H1 H 0.8486 0.4623 0.3773 0.016 Uiso 1 1 calc R U
C2 C 0.5506(3) 0.31133(13) 0.45944(14) 0.0127(3) Uani 1 1 d . .
C3 C 0.4809(3) 0.20784(15) 0.51994(14) 0.0158(4) Uani 1 1 d . .
H3 H 0.5797 0.1899 0.6021 0.019 Uiso 1 1 calc R U
C4 C 0.2708(3) 0.13069(14) 0.46286(14) 0.0169(4) Uani 1 1 d . .
H4 H 0.2271 0.0602 0.5052 0.020 Uiso 1 1 calc R U
C5 C 0.1236(3) 0.15721(14) 0.34271(14) 0.0140(3) Uani 1 1 d . .
C6 C 0.1898(3) 0.26155(14) 0.28183(14) 0.0152(3) Uani 1 1 d . .
H6 H 0.0886 0.2805 0.2004 0.018 Uiso 1 1 calc R U
C7 C 0.4013(3) 0.33714(14) 0.33933(14) 0.0142(3) Uani 1 1 d . .
H7 H 0.4458 0.4074 0.2968 0.017 Uiso 1 1 calc R U
N1 N 0.7651(3) 0.38630(11) 0.52636(11) 0.0130(3) Uani 1 1 d . .
O1 O -0.0844(2) 0.08059(10) 0.28930(10) 0.0190(3) Uani 1 1 d . .
H1A H -0.1377 0.0986 0.2135 0.028 Uiso 1 1 calc R U
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
N1 C1 C1 119.93(17) . 3_766
N1 C1 H1 120.0 . .
C1 C1 H1 120.0 3_766 .
C3 C2 C7 118.61(14) . .
C3 C2 N1 117.36(13) . .
C7 C2 N1 124.00(13) . .
C4 C3 C2 121.38(14) . .
C4 C3 H3 119.3 . .
C2 C3 H3 119.3 . .
C3 C4 C5 119.49(14) . .
C3 C4 H4 120.3 . .
C5 C4 H4 120.3 . .
O1 C5 C4 118.30(14) . .
O1 C5 C6 122.15(14) . .
C4 C5 C6 119.54(14) . .
C7 C6 C5 120.39(14) . .
C7 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C6 C7 C2 120.57(14) . .
C6 C7 H7 119.7 . .
C2 C7 H7 119.7 . .
C1 N1 C2 119.54(13) . .
C5 O1 H1A 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.287(2) .
C1 C1 1.450(3) 3_766
C1 H1 0.9500 .
C2 C3 1.395(2) .
C2 C7 1.396(2) .
C2 N1 1.4192(19) .
C3 C4 1.384(2) .
C3 H3 0.9500 .
C4 C5 1.395(2) .
C4 H4 0.9500 .
C5 O1 1.3619(18) .
C5 C6 1.399(2) .
C6 C7 1.379(2) .
C6 H6 0.9500 .
C7 H7 0.9500 .
O1 H1A 0.8400 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 O1 0.95 2.65 3.2725(19) 123.9 2
O1 H1A N1 0.84 2.01 2.8392(17) 169.9 4_465
