#------------------------------------------------------------------------------
#$Date: 2020-05-07 00:18:19 +0300 (Thu, 07 May 2020) $
#$Revision: 251829 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240468.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_7240468
loop_
_publ_author_name
'Zhang, Guoshun'
'shang, xiaoqing'
'han, wei'
'zhang, lifeng'
'ren, guolian'
'Zhang, Shuqiu'
_publ_section_title
;
 Synthesis, Structural Characterization, Physicochemical Properties and
 Transformations of Dehydroevodiamine and Its Hydrochloride Salts
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00136H
_journal_year                    2020
_chemical_formula_moiety         'C19 H17 N3 O2'
_chemical_formula_sum            'C19 H17 N3 O2'
_chemical_formula_weight         319.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-01-29 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                105.866(2)
_cell_angle_beta                 99.290(2)
_cell_angle_gamma                96.696(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9170(5)
_cell_length_b                   8.8668(7)
_cell_length_c                   14.1791(12)
_cell_measurement_reflns_used    3946
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.326
_cell_measurement_theta_min      3.028
_cell_volume                     813.61(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ωκ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8401
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_min         3.028
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ' Higashi, T. (1995)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       Bulk
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3946
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0489
_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)+(0.0617P)²+0.1472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1332
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2812
_reflns_number_total             3946
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00136h2.cif
_cod_data_source_block           DHED
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7240468
_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.
;
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.16869(18) 0.32392(18) 0.05677(10) 0.0705(4) Uani 1 1 d . . . . .
O2 O 0.28826(16) 0.11191(12) 0.04152(7) 0.0458(3) Uani 1 1 d . . . . .
N1 N 0.37415(19) -0.04315(14) -0.15062(9) 0.0400(3) Uani 1 1 d . . . . .
N2 N 0.04282(18) 0.21592(14) -0.03766(9) 0.0395(3) Uani 1 1 d . . . . .
N3 N -0.0160(3) 0.4125(2) 0.26066(12) 0.0635(4) Uani 1 1 d . . . . .
C1 C 0.5080(3) -0.1641(2) -0.30271(13) 0.0546(4) Uani 1 1 d . . . . .
H1B H 0.6048 -0.2083 -0.2710 0.066 Uiso 1 1 calc R U . . .
C2 C 0.4836(3) -0.1803(2) -0.40304(14) 0.0677(5) Uani 1 1 d . . . . .
H2A H 0.5659 -0.2365 -0.4398 0.081 Uiso 1 1 calc R U . . .
C3 C 0.3387(4) -0.1148(3) -0.45143(14) 0.0698(6) Uani 1 1 d . . . . .
H3B H 0.3260 -0.1287 -0.5197 0.084 Uiso 1 1 calc R U . . .
C4 C 0.2150(3) -0.0306(2) -0.40032(12) 0.0594(5) Uani 1 1 d . . . . .
H4A H 0.1196 0.0131 -0.4334 0.071 Uiso 1 1 calc R U . . .
C5 C 0.2337(2) -0.01083(17) -0.29732(11) 0.0426(3) Uani 1 1 d . . . . .
C6 C 0.3818(2) -0.07874(17) -0.24999(11) 0.0414(3) Uani 1 1 d . . . . .
C7 C 0.2273(2) 0.04708(16) -0.13449(10) 0.0362(3) Uani 1 1 d . . . . .
C8 C 0.1364(2) 0.06834(16) -0.22201(10) 0.0380(3) Uani 1 1 d . . . . .
C9 C -0.0256(2) 0.16571(19) -0.22216(12) 0.0458(4) Uani 1 1 d . . . . .
H9A H -0.1279 0.1180 -0.2821 0.055 Uiso 1 1 calc R U . . .
H9B H 0.0273 0.2721 -0.2219 0.055 Uiso 1 1 calc R U . . .
C10 C -0.1139(2) 0.17387(19) -0.12988(12) 0.0458(4) Uani 1 1 d . . . . .
H10A H -0.2009 0.2527 -0.1230 0.055 Uiso 1 1 calc R U . . .
H10B H -0.1932 0.0717 -0.1382 0.055 Uiso 1 1 calc R U . . .
C11 C 0.1927(2) 0.12364(16) -0.03588(10) 0.0356(3) Uani 1 1 d . . . . .
C12 C 0.1559(2) 0.45669(17) 0.23161(12) 0.0441(4) Uani 1 1 d . . . . .
C13 C 0.1737(2) 0.40868(16) 0.13015(11) 0.0395(3) Uani 1 1 d . . . . .
C14 C 0.0030(2) 0.31401(18) 0.05121(11) 0.0419(3) Uani 1 1 d . . . . .
C15 C 0.3508(2) 0.45955(19) 0.10457(13) 0.0506(4) Uani 1 1 d . . . . .
H15A H 0.3618 0.4278 0.0378 0.061 Uiso 1 1 calc R U . . .
C16 C 0.5093(3) 0.5548(2) 0.17465(16) 0.0656(5) Uani 1 1 d . . . . .
H16A H 0.6256 0.5886 0.1559 0.079 Uiso 1 1 calc R U . . .
C17 C 0.4924(3) 0.5995(2) 0.27360(16) 0.0675(5) Uani 1 1 d . . . . .
H17A H 0.5989 0.6641 0.3219 0.081 Uiso 1 1 calc R U . . .
C18 C 0.3214(3) 0.5505(2) 0.30227(14) 0.0569(4) Uani 1 1 d . . . . .
H18A H 0.3155 0.5802 0.3698 0.068 Uiso 1 1 calc R U . . .
C19 C -0.0350(4) 0.4509(3) 0.36375(15) 0.0840(7) Uani 1 1 d . . . . .
H19A H -0.1670 0.4089 0.3674 0.126 Uiso 1 1 calc R U . . .
H19B H 0.0597 0.4051 0.3997 0.126 Uiso 1 1 calc R U . . .
H19C H -0.0103 0.5643 0.3929 0.126 Uiso 1 1 calc R U . . .
H1A H 0.464(3) -0.064(2) -0.1031(14) 0.060(5) Uiso 1 1 d . . . . .
H3A H -0.122(3) 0.366(3) 0.2111(16) 0.080(7) 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
C6 N1 C7 107.84(12) . . ?
C6 N1 H1A 124.6(11) . . ?
C7 N1 H1A 127.0(11) . . ?
C11 N2 C14 121.60(12) . . ?
C11 N2 C10 118.13(12) . . ?
C14 N2 C10 117.71(12) . . ?
C12 N3 C19 123.01(17) . . ?
C12 N3 H3A 116.0(14) . . ?
C19 N3 H3A 120.8(14) . . ?
C2 C1 C6 117.42(18) . . ?
C2 C1 H1B 121.3 . . ?
C6 C1 H1B 121.3 . . ?
C1 C2 C3 121.80(18) . . ?
C1 C2 H2A 119.1 . . ?
C3 C2 H2A 119.1 . . ?
C4 C3 C2 121.17(17) . . ?
C4 C3 H3B 119.4 . . ?
C2 C3 H3B 119.4 . . ?
C3 C4 C5 119.28(17) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C4 C5 C6 118.43(15) . . ?
C4 C5 C8 134.70(15) . . ?
C6 C5 C8 106.86(12) . . ?
N1 C6 C1 129.86(15) . . ?
N1 C6 C5 108.23(13) . . ?
C1 C6 C5 121.90(15) . . ?
C8 C7 N1 110.72(13) . . ?
C8 C7 C11 125.43(13) . . ?
N1 C7 C11 123.46(12) . . ?
C7 C8 C5 106.34(13) . . ?
C7 C8 C9 120.14(14) . . ?
C5 C8 C9 133.47(13) . . ?
C8 C9 C10 109.13(12) . . ?
C8 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
N2 C10 C9 111.70(12) . . ?
N2 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
O2 C11 N2 123.16(13) . . ?
O2 C11 C7 123.58(13) . . ?
N2 C11 C7 113.24(12) . . ?
N3 C12 C18 120.67(16) . . ?
N3 C12 C13 121.66(14) . . ?
C18 C12 C13 117.67(15) . . ?
C15 C13 C12 119.24(14) . . ?
C15 C13 C14 120.07(14) . . ?
C12 C13 C14 120.59(13) . . ?
O1 C14 N2 118.68(14) . . ?
O1 C14 C13 123.19(14) . . ?
N2 C14 C13 117.97(12) . . ?
C16 C15 C13 122.12(17) . . ?
C16 C15 H15A 118.9 . . ?
C13 C15 H15A 118.9 . . ?
C15 C16 C17 118.49(17) . . ?
C15 C16 H16A 120.8 . . ?
C17 C16 H16A 120.8 . . ?
C16 C17 C18 121.32(17) . . ?
C16 C17 H17A 119.3 . . ?
C18 C17 H17A 119.3 . . ?
C17 C18 C12 121.12(17) . . ?
C17 C18 H18A 119.4 . . ?
C12 C18 H18A 119.4 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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
O1 C14 1.2146(18) . ?
O2 C11 1.2231(16) . ?
N1 C6 1.3684(19) . ?
N1 C7 1.3744(18) . ?
N1 H1A 0.916(19) . ?
N2 C11 1.3952(17) . ?
N2 C14 1.4102(19) . ?
N2 C10 1.4850(18) . ?
N3 C12 1.369(2) . ?
N3 C19 1.439(2) . ?
N3 H3A 0.90(2) . ?
C1 C2 1.370(3) . ?
C1 C6 1.396(2) . ?
C1 H1B 0.9300 . ?
C2 C3 1.394(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.367(3) . ?
C3 H3B 0.9300 . ?
C4 C5 1.405(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.416(2) . ?
C5 C8 1.421(2) . ?
C7 C8 1.3690(19) . ?
C7 C11 1.449(2) . ?
C8 C9 1.492(2) . ?
C9 C10 1.519(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C18 1.400(2) . ?
C12 C13 1.415(2) . ?
C13 C15 1.392(2) . ?
C13 C14 1.477(2) . ?
C15 C16 1.370(2) . ?
C15 H15A 0.9300 . ?
C16 C17 1.378(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.372(3) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
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
N3 H3A O1 0.90(2) 2.08(2) 2.769(2) 132.7(18) .
N1 H1A O2 0.916(19) 1.94(2) 2.8105(16) 158.4(16) 2_655
