#------------------------------------------------------------------------------
#$Date: 2021-01-07 08:11:56 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260735 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/57/7705725.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_7705725
loop_
_publ_author_name
'Zhang, Shanshan'
'Wang, Zheng'
'Cao, Qianrong'
'Yue, Erlin'
'Liu, Qingbin'
'Ma, Yanping'
'Liang, Tongling'
'Sun, Wen-Hua'
_publ_section_title
;
 Aza-crown compounds synthesised by the self-condensation of
 2-amino-benzyl alcohol over a pincer ruthenium catalyst and applied in
 the transfer hydrogenation of ketones.
;
_journal_issue                   44
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              15821
_journal_page_last               15827
_journal_paper_doi               10.1039/d0dt03257c
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C21 H21 N3'
_chemical_formula_sum            'C21 H21 N3'
_chemical_formula_weight         315.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-06-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-08 deposited with the CCDC.	2020-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.60(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8540(10)
_cell_length_b                   21.542(4)
_cell_length_c                   15.408(3)
_cell_measurement_reflns_used    5276
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4622
_cell_measurement_theta_min      1.3229
_cell_volume                     1609.5(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22322
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         1.626
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_correction_T_min  0.9896
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0687
_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)+(0.0623P)²+1.2038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1642
_refine_ls_wR_factor_ref         0.1665
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3542
_reflns_number_total             3689
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt03257c2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7705725--7705726.cif.'
_cod_original_cell_volume        1609.5(6)
_cod_database_code               7705725
_shelx_shelxl_version_number     2017/1
_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   0.994
_shelx_estimated_absorpt_t_min   0.990
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C14(H14A,H14B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), N2(H2), C2(H2A), C18(H18), C19(H19), C16(H16), C3(H3A),
 C5(H5), C9(H9), C17(H17), C4(H4), C11(H11), C12(H12), C10(H10)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
N1 N 0.4716(3) 0.12866(8) 0.20171(10) 0.0255(4) Uani 1 1 d . . . . .
H1 H 0.367191 0.095250 0.201105 0.031 Uiso 1 1 calc R . . . .
C1 C 0.6736(4) 0.13492(9) 0.13968(12) 0.0245(4) Uani 1 1 d . . . . .
N3 N 0.6159(4) 0.06819(8) 0.36668(11) 0.0308(4) Uani 1 1 d . . . . .
H3 H 0.443056 0.068420 0.346849 0.037 Uiso 1 1 calc R . . . .
C20 C 0.6657(4) 0.17836(9) 0.33583(12) 0.0250(4) Uani 1 1 d . . . . .
C15 C 0.7507(4) 0.12437(9) 0.38176(12) 0.0256(4) Uani 1 1 d . . . . .
N2 N 0.7292(4) -0.00096(8) 0.19468(12) 0.0330(4) Uani 1 1 d . . . . .
H2 H 0.888829 0.013910 0.214426 0.040 Uiso 1 1 calc R . . . .
C2 C 0.8190(4) 0.18969(9) 0.12693(12) 0.0276(4) Uani 1 1 d . . . . .
H2A H 0.787998 0.224750 0.162594 0.033 Uiso 1 1 calc R . . . .
C13 C 0.6009(4) -0.04253(9) 0.33483(13) 0.0298(4) Uani 1 1 d . . . . .
C18 C 1.0076(4) 0.23884(10) 0.41934(13) 0.0296(4) Uani 1 1 d . . . . .
H18 H 1.091854 0.277756 0.432316 0.036 Uiso 1 1 calc R . . . .
C19 C 0.7963(4) 0.23409(9) 0.35554(12) 0.0278(4) Uani 1 1 d . . . . .
H19 H 0.739711 0.270326 0.324446 0.033 Uiso 1 1 calc R . . . .
C16 C 0.9673(4) 0.12911(10) 0.44458(13) 0.0298(4) Uani 1 1 d . . . . .
H16 H 1.029586 0.092948 0.474796 0.036 Uiso 1 1 calc R . . . .
C3 C 1.0095(4) 0.19333(10) 0.06213(13) 0.0301(4) Uani 1 1 d . . . . .
H3A H 1.110581 0.230579 0.054736 0.036 Uiso 1 1 calc R . . . .
C5 C 0.9144(4) 0.08790(10) 0.02277(13) 0.0305(4) Uani 1 1 d . . . . .
H5 H 0.946255 0.053215 -0.013499 0.037 Uiso 1 1 calc R . . . .
C9 C 0.4345(5) -0.09162(10) 0.20131(14) 0.0363(5) Uani 1 1 d . . . . .
H9 H 0.423749 -0.093305 0.139641 0.044 Uiso 1 1 calc R . . . .
C17 C 1.0925(4) 0.18579(10) 0.46347(13) 0.0300(4) Uani 1 1 d . . . . .
H17 H 1.237334 0.188129 0.506936 0.036 Uiso 1 1 calc R . . . .
C6 C 0.7305(4) 0.08225(9) 0.08883(12) 0.0270(4) Uani 1 1 d . . . . .
C21 C 0.4317(4) 0.17643(9) 0.26697(12) 0.0271(4) Uani 1 1 d . . . . .
H21A H 0.256145 0.168512 0.295366 0.033 Uiso 1 1 calc R . . . .
H21B H 0.416851 0.217386 0.238001 0.033 Uiso 1 1 calc R . . . .
C14 C 0.7542(4) 0.00864(10) 0.38293(14) 0.0327(5) Uani 1 1 d . . . . .
H14A H 0.761942 -0.000340 0.446007 0.039 Uiso 1 1 calc R . . . .
H14B H 0.945631 0.010831 0.363531 0.039 Uiso 1 1 calc R . . . .
C4 C 1.0525(4) 0.14319(10) 0.00860(13) 0.0309(4) Uani 1 1 d . . . . .
H4 H 1.175346 0.146466 -0.037462 0.037 Uiso 1 1 calc R . . . .
C8 C 0.5886(4) -0.04486(9) 0.24311(13) 0.0294(4) Uani 1 1 d . . . . .
C11 C 0.3090(5) -0.13373(11) 0.33847(16) 0.0412(5) Uani 1 1 d . . . . .
H11 H 0.214163 -0.163822 0.370893 0.049 Uiso 1 1 calc R . . . .
C7 C 0.6084(4) 0.01995(9) 0.11103(13) 0.0299(4) Uani 1 1 d . . . . .
H7A H 0.405855 0.023681 0.114265 0.036 Uiso 1 1 calc R . . . .
H7B H 0.647706 -0.010655 0.065283 0.036 Uiso 1 1 calc R . . . .
C12 C 0.4614(5) -0.08728(10) 0.38058(15) 0.0351(5) Uani 1 1 d . . . . .
H12 H 0.470459 -0.086066 0.442279 0.042 Uiso 1 1 calc R . . . .
C10 C 0.2969(5) -0.13562(11) 0.24852(16) 0.0417(5) Uani 1 1 d . . . . .
H10 H 0.193663 -0.167297 0.219039 0.050 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'
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
C1 N1 C21 121.30(16) . . ?
N1 C1 C6 117.36(17) . . ?
C2 C1 N1 123.38(18) . . ?
C2 C1 C6 119.26(18) . . ?
C15 N3 C14 121.71(16) . . ?
C15 C20 C21 121.29(17) . . ?
C19 C20 C15 118.88(17) . . ?
C19 C20 C21 119.82(17) . . ?
N3 C15 C20 120.54(17) . . ?
N3 C15 C16 120.78(18) . . ?
C16 C15 C20 118.64(18) . . ?
C8 N2 C7 119.46(17) . . ?
C1 C2 C3 120.36(19) . . ?
C8 C13 C14 121.05(18) . . ?
C12 C13 C14 119.98(19) . . ?
C12 C13 C8 118.93(19) . . ?
C17 C18 C19 118.69(19) . . ?
C20 C19 C18 122.28(19) . . ?
C17 C16 C15 121.12(19) . . ?
C4 C3 C2 120.47(19) . . ?
C6 C5 C4 121.41(19) . . ?
C10 C9 C8 120.9(2) . . ?
C18 C17 C16 120.36(18) . . ?
C1 C6 C7 119.90(17) . . ?
C5 C6 C1 118.95(18) . . ?
C5 C6 C7 120.99(18) . . ?
N1 C21 C20 112.49(15) . . ?
N3 C14 C13 110.15(16) . . ?
C3 C4 C5 119.33(19) . . ?
N2 C8 C13 120.62(19) . . ?
C9 C8 N2 120.36(19) . . ?
C9 C8 C13 119.02(19) . . ?
C10 C11 C12 119.1(2) . . ?
N2 C7 C6 109.09(17) . . ?
C11 C12 C13 121.7(2) . . ?
C9 C10 C11 120.4(2) . . ?
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
N1 C1 1.407(2) . ?
N1 C21 1.458(2) . ?
C1 C2 1.393(3) . ?
C1 C6 1.413(3) . ?
N3 C15 1.390(3) . ?
N3 C14 1.464(3) . ?
C20 C15 1.413(3) . ?
C20 C19 1.385(3) . ?
C20 C21 1.519(3) . ?
C15 C16 1.400(3) . ?
N2 C8 1.401(3) . ?
N2 C7 1.463(3) . ?
C2 C3 1.394(3) . ?
C13 C14 1.506(3) . ?
C13 C8 1.413(3) . ?
C13 C12 1.389(3) . ?
C18 C19 1.392(3) . ?
C18 C17 1.383(3) . ?
C16 C17 1.389(3) . ?
C3 C4 1.381(3) . ?
C5 C6 1.389(3) . ?
C5 C4 1.389(3) . ?
C9 C8 1.395(3) . ?
C9 C10 1.385(3) . ?
C6 C7 1.512(3) . ?
C11 C12 1.388(3) . ?
C11 C10 1.385(3) . ?
