#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/13/4101353.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_4101353
loop_
_publ_author_name
'Lebel, Olivier'
'Maris, Thierry'
'Perron, Marie-Eve'
'Demers, Eric'
'Wuest, James D'
_publ_section_title
;
 The dark side of crystal engineering: creating glasses from small
 symmetric molecules that form multiple hydrogen bonds.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10372
_journal_page_last               10373
_journal_paper_doi               10.1021/ja063353s
_journal_volume                  128
_journal_year                    2006
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C21 H23 N5 O2, C H Cl3'
_chemical_formula_sum            'C22 H24 Cl3 N5 O2'
_chemical_formula_weight         496.81
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.790(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.7394(1)
_cell_length_b                   13.3588(6)
_cell_length_c                   19.2393(5)
_cell_measurement_reflns_used    18826
_cell_measurement_temperature    225(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.55
_cell_volume                     5772.5(3)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Nonius Kappa CCD server (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      225(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       ω/2φ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_av_sigmaI/netI    0.0611
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16419
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.61
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  60
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_correction_T_min  0.7260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       0.0019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         6596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.0701
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1290P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1973
_refine_ls_wR_factor_ref         0.2238
_reflns_number_gt                3656
_reflns_number_total             6596
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja063353ssi20060514_025906.cif
_cod_data_source_block           jw1027
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (33
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (45
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (50 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C22 H24 Cl3 N5 O2 '
_cod_database_code               4101353
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.32969(13) 0.1240(3) 0.27213(16) 0.0595(9) Uani 1 1 d . . .
H1A H 0.3246 0.1819 0.2991 0.089 Uiso 1 1 calc R . .
H1B H 0.3520 0.0730 0.3088 0.089 Uiso 1 1 calc R . .
H1C H 0.2910 0.0976 0.2385 0.089 Uiso 1 1 calc R . .
C2 C 0.33277(11) 0.2109(2) 0.16707(13) 0.0419(6) Uani 1 1 d . . .
C3 C 0.37049(10) 0.2368(2) 0.12467(13) 0.0360(6) Uani 1 1 d . . .
C4 C 0.45953(10) 0.26963(19) 0.12455(12) 0.0351(6) Uani 1 1 d . . .
C5 C 0.37598(10) 0.2765(2) 0.01505(12) 0.0381(6) Uani 1 1 d . . .
C6 C 0.37120(11) 0.3082(2) -0.11514(13) 0.0406(6) Uani 1 1 d . . .
C7 C 0.42206(11) 0.3653(2) -0.09898(14) 0.0441(7) Uani 1 1 d . . .
H7 H 0.4428 0.3926 -0.0498 0.053 Uiso 1 1 calc R . .
C8 C 0.44231(12) 0.3821(2) -0.15507(15) 0.0495(7) Uani 1 1 d . . .
C9 C 0.41014(15) 0.3416(3) -0.22748(18) 0.0640(9) Uani 1 1 d . . .
H9 H 0.4239 0.3518 -0.2656 0.077 Uiso 1 1 calc R . .
C10 C 0.35865(16) 0.2871(3) -0.24511(17) 0.0650(9) Uani 1 1 d . . .
C11 C 0.33996(13) 0.2693(2) -0.18721(14) 0.0509(7) Uani 1 1 d . . .
H11 H 0.3057 0.2305 -0.1975 0.061 Uiso 1 1 calc R . .
C12 C 0.49790(14) 0.4433(3) -0.1371(2) 0.0639(9) Uani 1 1 d . . .
H12A H 0.5281 0.4017 -0.1423 0.096 Uiso 1 1 calc R . .
H12B H 0.5126 0.4683 -0.0851 0.096 Uiso 1 1 calc R . .
H12C H 0.4887 0.4992 -0.1724 0.096 Uiso 1 1 calc R . .
C13 C 0.3230(2) 0.2436(4) -0.32461(19) 0.1057(17) Uani 1 1 d . . .
H13A H 0.2838 0.2242 -0.3295 0.159 Uiso 1 1 calc R . .
H13B H 0.3435 0.1854 -0.3319 0.159 Uiso 1 1 calc R . .
H13C H 0.3191 0.2936 -0.3630 0.159 Uiso 1 1 calc R . .
C14 C 0.56071(10) 0.3006(2) 0.13330(13) 0.0363(6) Uani 1 1 d . . .
C15 C 0.60768(10) 0.3628(2) 0.17708(13) 0.0399(6) Uani 1 1 d . . .
H15 H 0.6095 0.3897 0.2232 0.048 Uiso 1 1 calc R . .
C16 C 0.65188(11) 0.3853(2) 0.15299(15) 0.0445(6) Uani 1 1 d . . .
C17 C 0.64830(12) 0.3445(2) 0.08488(15) 0.0491(7) Uani 1 1 d . . .
H17 H 0.6781 0.3597 0.0683 0.059 Uiso 1 1 calc R . .
C18 C 0.60193(12) 0.2819(2) 0.04069(14) 0.0485(7) Uani 1 1 d . . .
C19 C 0.55758(11) 0.2609(2) 0.06540(14) 0.0428(6) Uani 1 1 d . . .
H19 H 0.5254 0.2195 0.0357 0.051 Uiso 1 1 calc R . .
C20 C 0.70239(13) 0.4546(3) 0.1997(2) 0.0632(9) Uani 1 1 d . . .
H20A H 0.7315 0.4183 0.2428 0.095 Uiso 1 1 calc R . .
H20B H 0.6869 0.5102 0.2183 0.095 Uiso 1 1 calc R . .
H20C H 0.7212 0.4798 0.1679 0.095 Uiso 1 1 calc R . .
C21 C 0.59944(16) 0.2361(3) -0.03183(18) 0.0709(10) Uani 1 1 d . . .
H21A H 0.6235 0.1758 -0.0197 0.106 Uiso 1 1 calc R . .
H21B H 0.6147 0.2834 -0.0575 0.106 Uiso 1 1 calc R . .
H21C H 0.5585 0.2194 -0.0652 0.106 Uiso 1 1 calc R . .
N1 N 0.42873(8) 0.24551(16) 0.16662(10) 0.0371(5) Uani 1 1 d . . .
N2 N 0.34055(8) 0.25067(18) 0.05058(10) 0.0418(5) Uani 1 1 d . . .
N3 N 0.43470(8) 0.28709(17) 0.04910(10) 0.0379(5) Uani 1 1 d . . .
N4 N 0.51854(8) 0.27656(17) 0.16312(10) 0.0382(5) Uani 1 1 d . . .
H4 H 0.5328 0.2650 0.2121 0.046 Uiso 1 1 calc . . .
N5 N 0.34693(8) 0.29051(19) -0.06128(11) 0.0451(6) Uani 1 1 d . . .
H5 H 0.3083 0.2884 -0.0799 0.054 Uiso 1 1 calc . . .
O1 O 0.36193(8) 0.15300(15) 0.22702(9) 0.0461(5) Uani 1 1 d . . .
O2 O 0.28277(8) 0.24064(19) 0.14768(10) 0.0616(6) Uani 1 1 d . . .
C22 C 0.25018(15) 0.4466(3) 0.03632(17) 0.0658(9) Uani 1 1 d . A 1
H22 H 0.2528 0.3733 0.0310 0.079 Uiso 1 1 calc R A 1
Cl1 Cl 0.22168(6) 0.50019(9) -0.05498(6) 0.0984(4) Uani 1 1 d . A 1
Cl2 Cl 0.20102(6) 0.47069(10) 0.07861(7) 0.1055(4) Uani 1 1 d . A 1
Cl3 Cl 0.32151(6) 0.49250(10) 0.09326(9) 0.1205(5) Uani 1 1 d . A 1
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_publ_flag
O1 C1 H1A 109.5 ?
O1 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
O1 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
O2 C2 O1 125.4(2) y
O2 C2 C3 123.0(2) y
O1 C2 C3 111.7(2) y
N2 C3 N1 128.3(2) y
N2 C3 C2 114.9(2) y
N1 C3 C2 116.67(19) y
N4 C4 N3 119.2(2) y
N4 C4 N1 116.10(19) y
N3 C4 N1 124.7(2) y
N3 C5 N5 119.7(2) y
N3 C5 N2 125.48(19) y
N5 C5 N2 114.8(2) y
C11 C6 C7 120.4(2) y
C11 C6 N5 116.3(2) y
C7 C6 N5 123.3(2) y
C8 C7 C6 120.2(2) y
C8 C7 H7 119.9 ?
C6 C7 H7 119.9 ?
C7 C8 C9 118.4(3) y
C7 C8 C12 120.1(3) y
C9 C8 C12 121.5(3) y
C10 C9 C8 122.2(3) y
C10 C9 H9 118.9 ?
C8 C9 H9 118.9 ?
C9 C10 C11 118.3(3) y
C9 C10 C13 122.2(3) y
C11 C10 C13 119.4(3) y
C6 C11 C10 120.5(3) y
C6 C11 H11 119.8 ?
C10 C11 H11 119.8 ?
C8 C12 H12A 109.5 ?
C8 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C8 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
C10 C13 H13A 109.5 ?
C10 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C10 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C19 C14 C15 120.3(2) y
C19 C14 N4 122.3(2) y
C15 C14 N4 117.3(2) y
C16 C15 C14 120.2(2) y
C16 C15 H15 119.9 ?
C14 C15 H15 119.9 ?
C17 C16 C15 118.9(2) y
C17 C16 C20 120.8(2) y
C15 C16 C20 120.3(2) y
C18 C17 C16 121.7(2) y
C18 C17 H17 119.2 ?
C16 C17 H17 119.2 ?
C17 C18 C19 118.7(2) y
C17 C18 C21 121.1(3) y
C19 C18 C21 120.2(3) y
C14 C19 C18 120.3(2) y
C14 C19 H19 119.8 ?
C18 C19 H19 119.8 ?
C16 C20 H20A 109.5 ?
C16 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C16 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
C18 C21 H21A 109.5 ?
C18 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
C18 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
C3 N1 C4 113.20(18) y
C3 N2 C5 113.02(19) y
C5 N3 C4 115.24(19) y
C4 N4 C14 127.43(18) y
C4 N4 H4 116.3 ?
C14 N4 H4 116.3 ?
C5 N5 C6 128.5(2) y
C5 N5 H5 115.8 ?
C6 N5 H5 115.8 ?
C2 O1 C1 116.1(2) y
CL1 C22 CL3 111.2(2) y
CL1 C22 CL2 109.0(2) y
CL3 C22 CL2 111.00(19) y
CL1 C22 H22 108.5 ?
CL3 C22 H22 108.5 ?
CL2 C22 H22 108.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.456(3) y
C1 H1a 0.97 ?
C1 H1b 0.97 ?
C1 H1c 0.97 ?
C2 O2 1.200(3) y
C2 O1 1.323(3) y
C2 C3 1.515(3) y
C3 N2 1.315(3) y
C3 N1 1.329(3) y
C4 N4 1.335(3) y
C4 N3 1.338(3) y
C4 N1 1.362(3) y
C5 N3 1.327(3) y
C5 N5 1.350(3) y
C5 N2 1.363(3) y
C6 C11 1.375(4) y
C6 C7 1.390(4) y
C6 N5 1.418(3) y
C7 C8 1.385(4) y
C7 H7 0.94 ?
C8 C9 1.391(4) y
C8 C12 1.510(4) y
C9 C10 1.381(5) y
C9 H9 0.94 ?
C10 C11 1.394(4) y
C10 C13 1.524(4) y
C11 H11 0.94 ?
C12 H12a 0.97 ?
C12 H12b 0.97 ?
C12 H12c 0.97 ?
C13 H13a 0.97 ?
C13 H13b 0.97 ?
C13 H13c 0.97 ?
C14 C19 1.382(3) y
C14 C15 1.389(3) y
C14 N4 1.422(3) y
C15 C16 1.388(3) y
C15 H15 0.94 ?
C16 C17 1.387(4) y
C16 C20 1.512(4) y
C17 C18 1.385(4) y
C17 H17 0.94 ?
C18 C19 1.395(4) y
C18 C21 1.501(4) y
C19 H19 0.94 ?
C20 H20a 0.97 ?
C20 H20b 0.97 ?
C20 H20c 0.97 ?
C21 H21a 0.97 ?
C21 H21b 0.97 ?
C21 H21c 0.97 ?
N4 H4 0.87 ?
N5 H5 0.87 ?
C22 Cl1 1.748(3) y
C22 Cl3 1.752(3) y
C22 Cl2 1.754(4) y
C22 H22 0.99 ?
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
N4 H4 N1 0.87 2.13 3.003(3) 176.3 2_655
N5 H5 O2 0.87 2.11 2.960(3) 164.5 7
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
O2 C2 C3 N2 -31.0(4) y
O1 C2 C3 N2 149.4(2) y
O2 C2 C3 N1 147.1(3) y
O1 C2 C3 N1 -32.5(3) y
C11 C6 C7 C8 -1.1(4) y
N5 C6 C7 C8 -178.0(2) y
C6 C7 C8 C9 0.8(4) y
C6 C7 C8 C12 -179.4(3) y
C7 C8 C9 C10 1.0(5) y
C12 C8 C9 C10 -178.8(3) y
C8 C9 C10 C11 -2.4(6) y
C8 C9 C10 C13 179.4(4) y
C7 C6 C11 C10 -0.4(5) y
N5 C6 C11 C10 176.8(3) y
C9 C10 C11 C6 2.1(5) y
C13 C10 C11 C6 -179.7(4) y
C19 C14 C15 C16 -0.1(4) y
N4 C14 C15 C16 176.9(2) y
C14 C15 C16 C17 -0.1(4) y
C14 C15 C16 C20 178.7(3) y
C15 C16 C17 C18 -0.2(4) y
C20 C16 C17 C18 -179.1(3) y
C16 C17 C18 C19 0.8(4) y
C16 C17 C18 C21 -178.4(3) y
C15 C14 C19 C18 0.8(4) y
N4 C14 C19 C18 -176.1(2) y
C17 C18 C19 C14 -1.1(4) y
C21 C18 C19 C14 178.1(3) y
N2 C3 N1 C4 -1.7(4) y
C2 C3 N1 C4 -179.5(2) y
N4 C4 N1 C3 -178.1(2) y
N3 C4 N1 C3 2.5(4) y
N1 C3 N2 C5 0.5(4) y
C2 C3 N2 C5 178.3(2) y
N3 C5 N2 C3 0.3(4) y
N5 C5 N2 C3 179.4(2) y
N5 C5 N3 C4 -178.6(2) y
N2 C5 N3 C4 0.4(4) y
N4 C4 N3 C5 178.7(2) y
N1 C4 N3 C5 -1.9(4) y
N3 C4 N4 C14 -0.4(4) y
N1 C4 N4 C14 -179.9(2) y
C19 C14 N4 C4 -42.9(4) y
C15 C14 N4 C4 140.1(3) y
N3 C5 N5 C6 5.7(4) y
N2 C5 N5 C6 -173.4(3) y
C11 C6 N5 C5 146.7(3) y
C7 C6 N5 C5 -36.2(4) y
O2 C2 O1 C1 0.1(4) y
C3 C2 O1 C1 179.7(2) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660018
