#------------------------------------------------------------------------------
#$Date: 2020-05-07 00:18:19 +0300 (Thu, 07 May 2020) $
#$Revision: 251829 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240466.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_7240466
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 H16 N3 O, Cl, 3(H2 O) '
_chemical_formula_sum            'C19 H22 Cl N3 O4'
_chemical_formula_weight         391.84
_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   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                90
_cell_angle_beta                 98.9720(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1708(2)
_cell_length_b                   17.5834(6)
_cell_length_c                   14.7293(5)
_cell_measurement_reflns_used    5419
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.190
_cell_measurement_theta_min      2.800
_cell_volume                     1834.45(10)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ωκ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22958
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.190
_diffrn_reflns_theta_min         2.800
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ' Higashi, T. (1995)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       Bulk
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0468
_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)+(0.0825P)²+0.3670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1451
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4090
_reflns_number_total             5419
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00136h2.cif
_cod_data_source_block           DHEDHCl3H2O
_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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7240466
_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+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
Cl1 Cl 0.35492(7) 0.45102(3) 0.34791(3) 0.05568(15) Uani 1 1 d . . . . .
O1 O 0.28917(19) 0.50439(6) 1.02432(8) 0.0501(3) Uani 1 1 d . . . . .
O2 O 0.2729(3) 0.46129(14) 0.55619(14) 0.0790(6) Uani 1 1 d . . . . .
O3 O -0.0557(3) 0.42014(8) 0.62044(13) 0.0655(4) Uani 1 1 d . . . . .
O4 O 0.3401(2) 0.37383(9) 0.14713(11) 0.0606(4) Uani 1 1 d . . . . .
N1 N 0.13790(17) 0.78547(7) 0.80135(8) 0.0315(2) Uani 1 1 d . . . . .
N2 N 0.25685(16) 0.60740(6) 0.93046(8) 0.0283(2) Uani 1 1 d . . . . .
N3 N 0.37536(15) 0.72682(6) 0.98048(7) 0.0255(2) Uani 1 1 d . . . . .
C1 C -0.0041(2) 0.84549(10) 0.65333(11) 0.0430(4) Uani 1 1 d . . . . .
H1B H -0.0065 0.8947 0.6761 0.052 Uiso 1 1 calc R U . . .
C2 C -0.0684(2) 0.82904(12) 0.56265(12) 0.0511(5) Uani 1 1 d . . . . .
H2A H -0.1157 0.8682 0.5232 0.061 Uiso 1 1 calc R U . . .
C3 C -0.0648(2) 0.75489(13) 0.52777(11) 0.0532(5) Uani 1 1 d . . . . .
H3A H -0.1093 0.7463 0.4659 0.064 Uiso 1 1 calc R U . . .
C4 C 0.0032(2) 0.69439(11) 0.58301(10) 0.0442(4) Uani 1 1 d . . . . .
H4A H 0.0051 0.6454 0.5594 0.053 Uiso 1 1 calc R U . . .
C5 C 0.06950(19) 0.70943(9) 0.67633(9) 0.0334(3) Uani 1 1 d . . . . .
C6 C 0.06540(19) 0.78434(8) 0.70982(9) 0.0329(3) Uani 1 1 d . . . . .
C7 C 0.18640(18) 0.71128(7) 0.82755(9) 0.0278(3) Uani 1 1 d . . . . .
C8 C 0.14410(19) 0.66336(8) 0.75237(9) 0.0311(3) Uani 1 1 d . . . . .
C9 C 0.1779(2) 0.58039(8) 0.76247(10) 0.0378(3) Uani 1 1 d . . . . .
H9A H 0.3060 0.5683 0.7539 0.045 Uiso 1 1 calc R U . . .
H9B H 0.0914 0.5528 0.7169 0.045 Uiso 1 1 calc R U . . .
C10 C 0.1469(2) 0.55849(8) 0.85815(10) 0.0378(3) Uani 1 1 d . . . . .
H10A H 0.0136 0.5627 0.8622 0.045 Uiso 1 1 calc R U . . .
H10B H 0.1837 0.5058 0.8695 0.045 Uiso 1 1 calc R U . . .
C11 C 0.27620(17) 0.68360(7) 0.91548(8) 0.0253(2) Uani 1 1 d . . . . .
C12 C 0.44157(18) 0.69789(7) 1.06896(8) 0.0264(2) Uani 1 1 d . . . . .
C13 C 0.41866(19) 0.62074(7) 1.08608(9) 0.0293(3) Uani 1 1 d . . . . .
C14 C 0.3215(2) 0.57177(7) 1.01478(9) 0.0316(3) Uani 1 1 d . . . . .
C15 C 0.4836(2) 0.59084(9) 1.17342(10) 0.0379(3) Uani 1 1 d . . . . .
H15A H 0.4663 0.5396 1.1851 0.045 Uiso 1 1 calc R U . . .
C16 C 0.5728(2) 0.63709(10) 1.24184(10) 0.0420(3) Uani 1 1 d . . . . .
H16A H 0.6196 0.6170 1.2993 0.050 Uiso 1 1 calc R U . . .
C17 C 0.5924(2) 0.71410(9) 1.22456(10) 0.0393(3) Uani 1 1 d . . . . .
H17A H 0.6508 0.7454 1.2715 0.047 Uiso 1 1 calc R U . . .
C18 C 0.5274(2) 0.74546(8) 1.13953(9) 0.0338(3) Uani 1 1 d . . . . .
H18A H 0.5405 0.7973 1.1293 0.041 Uiso 1 1 calc R U . . .
C19 C 0.4302(2) 0.80537(8) 0.96101(10) 0.0359(3) Uani 1 1 d . . . . .
H19A H 0.5568 0.8148 0.9909 0.054 Uiso 1 1 calc R U . . .
H19B H 0.3457 0.8405 0.9836 0.054 Uiso 1 1 calc R U . . .
H19C H 0.4236 0.8119 0.8959 0.054 Uiso 1 1 calc R U . . .
H4B H 0.328(3) 0.4163(16) 0.1121(18) 0.073(7) Uiso 1 1 d . . . . .
H4C H 0.338(4) 0.3929(15) 0.200(2) 0.081(8) Uiso 1 1 d . . . . .
H3C H 0.029(4) 0.4353(15) 0.5981(19) 0.076(8) Uiso 1 1 d . . . . .
H2B H 0.285(5) 0.4635(19) 0.504(3) 0.102(11) Uiso 1 1 d . . . . .
H2C H 0.332(5) 0.495(2) 0.574(2) 0.099(13) Uiso 1 1 d . . . . .
H3B H -0.129(4) 0.4532(16) 0.6276(19) 0.075(8) Uiso 1 1 d . . . . .
H1A H 0.125(3) 0.8239(11) 0.8349(13) 0.044(5) 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'
Cl Cl 0.1484 0.1585 '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
H2B O2 H2C 100(3) . . ?
H3C O3 H3B 112(3) . . ?
H4B O4 H4C 101(2) . . ?
C6 N1 C7 107.48(12) . . ?
C6 N1 H1A 121.7(13) . . ?
C7 N1 H1A 129.0(13) . . ?
C11 N2 C14 123.49(11) . . ?
C11 N2 C10 120.26(11) . . ?
C14 N2 C10 116.01(11) . . ?
C11 N3 C12 121.42(10) . . ?
C11 N3 C19 121.38(10) . . ?
C12 N3 C19 117.10(11) . . ?
C2 C1 C6 116.71(17) . . ?
C2 C1 H1B 121.6 . . ?
C6 C1 H1B 121.6 . . ?
C1 C2 C3 121.94(16) . . ?
C1 C2 H2A 119.0 . . ?
C3 C2 H2A 119.0 . . ?
C4 C3 C2 121.66(16) . . ?
C4 C3 H3A 119.2 . . ?
C2 C3 H3A 119.2 . . ?
C3 C4 C5 117.71(17) . . ?
C3 C4 H4A 121.1 . . ?
C5 C4 H4A 121.1 . . ?
C4 C5 C6 119.70(14) . . ?
C4 C5 C8 133.82(15) . . ?
C6 C5 C8 106.48(12) . . ?
N1 C6 C1 128.25(15) . . ?
N1 C6 C5 109.48(12) . . ?
C1 C6 C5 122.28(14) . . ?
C8 C7 N1 109.55(12) . . ?
C8 C7 C11 121.66(12) . . ?
N1 C7 C11 128.71(12) . . ?
C7 C8 C5 106.99(12) . . ?
C7 C8 C9 120.38(12) . . ?
C5 C8 C9 132.63(13) . . ?
C8 C9 C10 107.38(12) . . ?
C8 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
C8 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
N2 C10 C9 112.34(12) . . ?
N2 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
N3 C11 N2 119.81(11) . . ?
N3 C11 C7 124.47(11) . . ?
N2 C11 C7 115.72(11) . . ?
C13 C12 C18 119.85(12) . . ?
C13 C12 N3 119.07(11) . . ?
C18 C12 N3 121.08(11) . . ?
C12 C13 C15 119.98(13) . . ?
C12 C13 C14 120.25(11) . . ?
C15 C13 C14 119.73(12) . . ?
O1 C14 N2 119.53(13) . . ?
O1 C14 C13 124.90(13) . . ?
N2 C14 C13 115.53(11) . . ?
C16 C15 C13 120.14(14) . . ?
C16 C15 H15A 119.9 . . ?
C13 C15 H15A 119.9 . . ?
C15 C16 C17 119.46(14) . . ?
C15 C16 H16A 120.3 . . ?
C17 C16 H16A 120.3 . . ?
C18 C17 C16 121.72(14) . . ?
C18 C17 H17A 119.1 . . ?
C16 C17 H17A 119.1 . . ?
C17 C18 C12 118.81(13) . . ?
C17 C18 H18A 120.6 . . ?
C12 C18 H18A 120.6 . . ?
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 1.2196(17) . ?
O2 H2B 0.79(4) . ?
O2 H2C 0.75(3) . ?
O3 H3C 0.78(3) . ?
O3 H3B 0.80(3) . ?
O4 H4B 0.90(3) . ?
O4 H4C 0.86(3) . ?
N1 C6 1.3674(18) . ?
N1 C7 1.3892(16) . ?
N1 H1A 0.85(2) . ?
N2 C11 1.3684(16) . ?
N2 C14 1.4037(17) . ?
N2 C10 1.4946(17) . ?
N3 C11 1.3370(16) . ?
N3 C12 1.4105(15) . ?
N3 C19 1.4762(16) . ?
C1 C2 1.374(2) . ?
C1 C6 1.403(2) . ?
C1 H1B 0.9300 . ?
C2 C3 1.403(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.381(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.408(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.408(2) . ?
C5 C8 1.4179(19) . ?
C7 C8 1.3868(18) . ?
C7 C11 1.4384(17) . ?
C8 C9 1.483(2) . ?
C9 C10 1.511(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C13 1.3941(18) . ?
C12 C18 1.3999(18) . ?
C13 C15 1.4005(18) . ?
C13 C14 1.4495(19) . ?
C15 C16 1.373(2) . ?
C15 H15A 0.9300 . ?
C16 C17 1.389(2) . ?
C16 H16A 0.9300 . ?
C17 C18 1.381(2) . ?
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
O2 H2B Cl1 0.79(4) 2.44(4) 3.218(2) 170(3) .
O2 H2C Cl1 0.75(3) 2.55(3) 3.213(2) 150(3) 3_666
O3 H3C O2 0.78(3) 2.00(3) 2.769(3) 170(3) .
O3 H3B Cl1 0.80(3) 2.40(3) 3.2040(19) 178(3) 3_566
O4 H4C Cl1 0.86(3) 2.39(3) 3.2405(17) 175(3) .
O4 H4B O1 0.90(3) 2.01(3) 2.9103(19) 175(2) 1_554
N1 H1A O3 0.85(2) 1.91(2) 2.7375(19) 164.2(18) 2_556
