#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:00:38 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179648 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/01/4510127.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_4510127
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            'C14 H21 N4 O2'
_chemical_formula_weight         277.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                   22.389(3)
_cell_length_b                   8.2386(11)
_cell_length_c                   16.762(14)
_cell_measurement_reflns_used    1356
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18.62
_cell_measurement_theta_min      2.43
_cell_volume                     3092(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0892
_diffrn_reflns_av_sigmaI/netI    0.0661
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14587
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0040(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   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2717
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1066P)²+0.5100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1808
_refine_ls_wR_factor_ref         0.2178
_reflns_number_gt                1510
_reflns_number_total             2717
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg4017454_si_002.cif
_cod_data_source_block           1
_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      'Pbcn '
_cod_database_code               4510127
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.57439(19) 1.2211(5) 0.7025(2) 0.0789(12) Uani 1 1 d .
H1A H 0.5417 1.1510 0.6888 0.118 Uiso 1 1 calc R
H1B H 0.5939 1.2571 0.6546 0.118 Uiso 1 1 calc R
H1C H 0.5596 1.3134 0.7313 0.118 Uiso 1 1 calc R
C2 C 0.61749(15) 1.1317(4) 0.75269(19) 0.0536(9) Uani 1 1 d .
C3 C 0.65392(14) 1.0049(3) 0.73265(17) 0.0495(8) Uani 1 1 d .
C4 C 0.68430(16) 0.9671(4) 0.80158(18) 0.0593(9) Uani 1 1 d .
C5 C 0.7296(2) 0.8431(5) 0.8175(2) 0.0979(15) Uani 1 1 d .
H5A H 0.7561 0.8350 0.7726 0.147 Uiso 1 1 calc R
H5B H 0.7105 0.7404 0.8262 0.147 Uiso 1 1 calc R
H5C H 0.7520 0.8727 0.8641 0.147 Uiso 1 1 calc R
C6 C 0.7049(2) 1.1602(4) 0.5715(2) 0.0762(11) Uani 1 1 d .
H6A H 0.6741 1.2362 0.5576 0.114 Uiso 1 1 calc R
H6B H 0.7334 1.1535 0.5289 0.114 Uiso 1 1 calc R
H6C H 0.7246 1.1958 0.6193 0.114 Uiso 1 1 calc R
C7 C 0.67808(14) 0.9988(4) 0.58511(17) 0.0510(8) Uani 1 1 d .
C8 C 0.65815(14) 0.9296(4) 0.65443(17) 0.0500(8) Uani 1 1 d .
C9 C 0.63799(16) 0.7798(4) 0.63224(19) 0.0590(9) Uani 1 1 d .
C10 C 0.6117(2) 0.6494(5) 0.6825(2) 0.1007(16) Uani 1 1 d .
H10A H 0.6431 0.5869 0.7064 0.151 Uiso 1 1 calc R
H10B H 0.5873 0.5800 0.6500 0.151 Uiso 1 1 calc R
H10C H 0.5876 0.6973 0.7237 0.151 Uiso 1 1 calc R
C11 C 0.4176(2) 0.5442(5) 0.5758(3) 0.0784(12) Uani 1 1 d U
C12 C 0.4425(3) 0.7064(5) 0.5899(3) 0.1005(16) Uani 1 1 d .
H12A H 0.4123 0.7716 0.6162 0.121 Uiso 1 1 calc R
H12B H 0.4758 0.6959 0.6266 0.121 Uiso 1 1 calc R
C13 C 0.46311(18) 0.7943(4) 0.5193(2) 0.0660(10) Uani 1 1 d .
H13A H 0.4294 0.8091 0.4836 0.079 Uiso 1 1 calc R
H13B H 0.4922 0.7274 0.4917 0.079 Uiso 1 1 calc R
C14 C 0.49021(17) 0.9543(4) 0.5348(2) 0.0678(10) Uani 1 1 d .
H14A H 0.4614 1.0198 0.5637 0.081 Uiso 1 1 calc R
H14B H 0.5244 0.9387 0.5695 0.081 Uiso 1 1 calc R
N1 N 0.62477(13) 1.1676(3) 0.82829(16) 0.0603(8) Uani 1 1 d .
N2 N 0.66555(14) 1.0663(4) 0.85824(16) 0.0643(8) Uani 1 1 d .
H2 H 0.6777 1.0657 0.9069 0.077 Uiso 1 1 calc R
N3 N 0.64557(13) 0.7622(3) 0.55542(15) 0.0603(8) Uani 1 1 d .
H3 H 0.6361 0.6773 0.5284 0.072 Uiso 1 1 calc R
N4 N 0.67015(12) 0.8962(3) 0.52560(15) 0.0554(8) Uani 1 1 d .
O1 O 0.38983(18) 0.5154(4) 0.5159(2) 0.1266(14) Uani 1 1 d .
O2 O 0.42725(19) 0.4442(4) 0.6286(2) 0.1498(17) Uani 1 1 d U
H2A H 0.4121 0.3571 0.6163 0.225 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'
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
N1 C2 C3 109.6(3) .
N1 C2 C1 121.3(3) .
C3 C2 C1 129.1(3) .
C2 C3 C4 105.1(3) .
C2 C3 C8 125.9(3) .
C4 C3 C8 128.9(3) .
N2 C4 C3 107.8(3) .
N2 C4 C5 121.4(3) .
C3 C4 C5 130.8(3) .
N4 C7 C8 109.3(3) .
N4 C7 C6 121.0(3) .
C8 C7 C6 129.7(3) .
C9 C8 C7 104.6(3) .
C9 C8 C3 127.6(3) .
C7 C8 C3 127.5(3) .
N3 C9 C8 109.0(3) .
N3 C9 C10 122.0(3) .
C8 C9 C10 129.0(3) .
O1 C11 O2 124.0(4) .
O1 C11 C12 120.7(4) .
O2 C11 C12 115.3(4) .
C13 C12 C11 116.1(4) .
C12 C13 C14 115.5(3) .
C14 C14 C13 116.4(4) 5_676
C2 N1 N2 107.9(3) .
C4 N2 N1 109.5(3) .
C9 N3 N4 109.4(3) .
C7 N4 N3 107.6(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.478(5) .
C2 N1 1.312(4) .
C2 C3 1.367(4) .
C3 C4 1.376(4) .
C3 C8 1.453(4) .
C4 N2 1.322(4) .
C4 C5 1.464(5) .
C6 C7 1.477(4) .
C7 N4 1.319(4) .
C7 C8 1.369(4) .
C8 C9 1.366(4) .
C9 N3 1.307(4) .
C9 C10 1.487(5) .
C11 O1 1.205(5) .
C11 O2 1.229(5) .
C11 C12 1.467(5) .
C12 C13 1.463(5) .
C13 C14 1.475(5) .
C14 C14 1.456(7) 5_676
N1 N2 1.335(4) .
N3 N4 1.331(4) .
