#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:00:38 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179648 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/01/4510128.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_4510128
loop_
_publ_author_name
'Han, Lu-Lu'
'Li, Zhong-Hui'
'Chen, Jiang-Shan'
'Wang, Xing-Po'
'Sun, Di'
_publ_section_title
;
 Solution and Mechanochemical Syntheses of Two Novel Cocrystals: Ligand
 Length Modulated Interpenetration of Hydrogen-Bonded 2D 63-hcb Networks
 Based on a Robust Trimeric Heterosynthon
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1221
_journal_paper_doi               10.1021/cg4017454
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C15 H23 N4 O2'
_chemical_formula_weight         291.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.5238(9)
_cell_length_b                   16.626(2)
_cell_length_c                   26.574(3)
_cell_measurement_reflns_used    1484
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.37
_cell_measurement_theta_min      2.89
_cell_volume                     3324.2(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0919
_diffrn_reflns_av_sigmaI/netI    0.0755
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            14051
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_correction_T_min  0.9905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0060(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.0656
_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)+(0.0722P)²+1.2448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1553
_refine_ls_wR_factor_ref         0.1830
_reflns_number_gt                1687
_reflns_number_total             2906
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg4017454_si_002.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'Pbca '
_cod_database_code               4510128
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.0979(4) 0.0623(2) 0.20543(16) 0.0729(12) Uani 1 1 d .
H1A H 0.0097 0.0692 0.1797 0.109 Uiso 1 1 calc R
H1B H 0.0785 0.1011 0.2317 0.109 Uiso 1 1 calc R
H1C H 0.0892 0.0091 0.2191 0.109 Uiso 1 1 calc R
C2 C 0.2771(4) 0.07419(19) 0.18357(12) 0.0460(8) Uani 1 1 d .
C3 C 0.3524(4) 0.14408(18) 0.16421(12) 0.0459(8) Uani 1 1 d .
C4 C 0.5207(4) 0.12230(19) 0.14890(13) 0.0522(9) Uani 1 1 d .
C5 C 0.6639(5) 0.1700(3) 0.12438(19) 0.0937(15) Uani 1 1 d .
H5A H 0.7284 0.1994 0.1495 0.141 Uiso 1 1 calc R
H5B H 0.6122 0.2069 0.1008 0.141 Uiso 1 1 calc R
H5C H 0.7435 0.1343 0.1070 0.141 Uiso 1 1 calc R
C6 C 0.3792(5) 0.3041(3) 0.23537(16) 0.0859(14) Uani 1 1 d .
H6A H 0.4849 0.3334 0.2269 0.129 Uiso 1 1 calc R
H6B H 0.4113 0.2537 0.2505 0.129 Uiso 1 1 calc R
H6C H 0.3095 0.3349 0.2587 0.129 Uiso 1 1 calc R
C7 C 0.2740(4) 0.28895(19) 0.18916(13) 0.0497(8) Uani 1 1 d .
C8 C 0.2657(4) 0.22301(18) 0.15827(12) 0.0453(8) Uani 1 1 d .
C9 C 0.1501(4) 0.24453(18) 0.11995(12) 0.0449(8) Uani 1 1 d .
C10 C 0.1002(5) 0.1985(2) 0.07446(15) 0.0663(11) Uani 1 1 d .
H10A H 0.0002 0.2238 0.0585 0.099 Uiso 1 1 calc R
H10B H 0.0694 0.1445 0.0838 0.099 Uiso 1 1 calc R
H10C H 0.1987 0.1974 0.0515 0.099 Uiso 1 1 calc R
C11 C 0.6600(4) 0.4030(2) 0.08840(14) 0.0529(9) Uani 1 1 d .
C12 C 0.4943(4) 0.3895(2) 0.05901(14) 0.0557(9) Uani 1 1 d .
H12A H 0.4343 0.3429 0.0730 0.067 Uiso 1 1 calc R
H12B H 0.5277 0.3762 0.0248 0.067 Uiso 1 1 calc R
C13 C 0.3635(4) 0.4574(2) 0.05702(13) 0.0497(8) Uani 1 1 d .
H13A H 0.4253 0.5064 0.0477 0.060 Uiso 1 1 calc R
H13B H 0.3132 0.4653 0.0903 0.060 Uiso 1 1 calc R
C14 C 0.2143(4) 0.4424(2) 0.01991(13) 0.0531(9) Uani 1 1 d .
H14A H 0.2649 0.4374 -0.0135 0.064 Uiso 1 1 calc R
H14B H 0.1582 0.3915 0.0281 0.064 Uiso 1 1 calc R
C15 C 0.0730(4) 0.5072(2) 0.01886(13) 0.0546(9) Uani 1 1 d .
H15A H 0.0205 0.5115 0.0521 0.065 Uiso 1 1 calc R
H15B H 0.1292 0.5583 0.0113 0.065 Uiso 1 1 calc R
N1 N 0.5408(3) 0.04437(16) 0.15915(11) 0.0554(8) Uani 1 1 d .
H1 H 0.6359 0.0174 0.1530 0.066 Uiso 1 1 calc R
N2 N 0.3927(3) 0.01313(15) 0.18045(10) 0.0497(7) Uani 1 1 d .
N3 N 0.1676(3) 0.34528(15) 0.16966(11) 0.0530(7) Uani 1 1 d .
H3 H 0.1511 0.3921 0.1826 0.064 Uiso 1 1 calc R
N4 N 0.0902(3) 0.31906(16) 0.12730(11) 0.0498(7) Uani 1 1 d .
O1 O 0.7864(3) 0.35328(17) 0.07777(11) 0.0844(9) Uani 1 1 d .
H1D H 0.8737 0.3636 0.0950 0.127 Uiso 1 1 calc R
O2 O 0.6727(3) 0.4558(2) 0.11920(12) 0.0985(11) Uani 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
C2 C1 H1A 109.5 .
C2 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
C2 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
N2 C2 C3 110.2(3) .
N2 C2 C1 121.0(3) .
C3 C2 C1 128.8(3) .
C4 C3 C2 105.3(3) .
C4 C3 C8 127.5(3) .
C2 C3 C8 127.1(3) .
N1 C4 C3 107.4(3) .
N1 C4 C5 121.7(3) .
C3 C4 C5 130.9(3) .
C4 C5 H5A 109.5 .
C4 C5 H5B 109.5 .
H5A C5 H5B 109.5 .
C4 C5 H5C 109.5 .
H5A C5 H5C 109.5 .
H5B C5 H5C 109.5 .
C7 C6 H6A 109.5 .
C7 C6 H6B 109.5 .
H6A C6 H6B 109.5 .
C7 C6 H6C 109.5 .
H6A C6 H6C 109.5 .
H6B C6 H6C 109.5 .
N3 C7 C8 107.5(3) .
N3 C7 C6 121.5(3) .
C8 C7 C6 131.0(3) .
C7 C8 C9 105.2(3) .
C7 C8 C3 128.9(3) .
C9 C8 C3 125.9(3) .
N4 C9 C8 110.1(3) .
N4 C9 C10 121.0(3) .
C8 C9 C10 128.8(3) .
C9 C10 H10A 109.5 .
C9 C10 H10B 109.5 .
H10A C10 H10B 109.5 .
C9 C10 H10C 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
O2 C11 O1 123.8(3) .
O2 C11 C12 122.2(3) .
O1 C11 C12 113.9(3) .
C11 C12 C13 117.1(3) .
C11 C12 H12A 108.0 .
C13 C12 H12A 108.0 .
C11 C12 H12B 108.0 .
C13 C12 H12B 108.0 .
H12A C12 H12B 107.3 .
C12 C13 C14 112.7(3) .
C12 C13 H13A 109.1 .
C14 C13 H13A 109.1 .
C12 C13 H13B 109.1 .
C14 C13 H13B 109.1 .
H13A C13 H13B 107.8 .
C15 C14 C13 114.5(3) .
C15 C14 H14A 108.6 .
C13 C14 H14A 108.6 .
C15 C14 H14B 108.6 .
C13 C14 H14B 108.6 .
H14A C14 H14B 107.6 .
C15 C15 C14 114.2(4) 5_565
C15 C15 H15A 108.7 5_565
C14 C15 H15A 108.7 .
C15 C15 H15B 108.7 5_565
C14 C15 H15B 108.7 .
H15A C15 H15B 107.6 .
C4 N1 N2 111.4(2) .
C4 N1 H1 124.3 .
N2 N1 H1 124.3 .
C2 N2 N1 105.6(2) .
C7 N3 N4 111.0(3) .
C7 N3 H3 124.5 .
N4 N3 H3 124.5 .
C9 N4 N3 106.2(2) .
C11 O1 H1D 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.481(4) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 N2 1.339(4) .
C2 C3 1.391(4) .
C3 C4 1.379(4) .
C3 C8 1.474(4) .
C4 N1 1.333(4) .
C4 C5 1.488(5) .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
C6 C7 1.482(5) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 N3 1.337(4) .
C7 C8 1.371(4) .
C8 C9 1.386(4) .
C9 N4 1.333(4) .
C9 C10 1.479(5) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 O2 1.203(4) .
C11 O1 1.292(4) .
C11 C12 1.488(5) .
C12 C13 1.498(4) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.515(4) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 C15 1.514(4) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C15 1.506(6) 5_565
C15 H15A 0.9700 .
C15 H15B 0.9700 .
N1 N2 1.354(3) .
N1 H1 0.8600 .
N3 N4 1.340(4) .
N3 H3 0.8600 .
O1 H1D 0.8200 .
