#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:26:59 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179579 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/44/4504459.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_4504459
loop_
_publ_author_name
'Rajput, Lalit'
'Singha, Subhankar'
'Biradha, Kumar'
_publ_section_title
;
 Comparative Structural Studies on Homologues of Amides and Reverse
 Amides: Unprecedented 4-fold Interpenetrated Quartz Network, New
 β-Sheet, and Two-Dimensional Layers
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2788
_journal_paper_doi               10.1021/cg0706417
_journal_volume                  7
_journal_year                    2007
_chemical_formula_sum            'C18 H26 N4 O4'
_chemical_formula_weight         362.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 109.33(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.694(2)
_cell_length_b                   11.655(2)
_cell_length_c                   15.421(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      8
_cell_volume                     1983.3(7)
_computing_cell_refinement       CAD4
_computing_data_collection       CAD4
_computing_data_reduction        CAD4
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       ω-scan
_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  0.2322
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3560
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.007(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1301
_refine_ls_R_factor_gt           0.0760
_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)+(0.1745P)²+1.5774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2697
_refine_ls_wR_factor_ref         0.3111
_reflns_number_gt                2115
_reflns_number_total             3381
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0706417-file002.cif
_cod_data_source_block           6c
_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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4504459
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1W O 0.8443(3) 0.3406(3) 0.2063(2) 0.0797(11) Uani 1 1 d .
O2W O 0.9281(4) 0.1618(4) 0.0151(3) 0.1185(18) Uani 1 1 d .
O8 O 0.7727(3) -0.0073(4) 0.0392(2) 0.0894(12) Uani 1 1 d .
N11 N 1.8653(4) -0.1518(5) 0.8313(3) 0.0850(14) Uani 1 1 d .
N12 N 1.5462(3) -0.1690(3) 0.6064(2) 0.0649(11) Uani 1 1 d .
H12 H 1.5487 -0.2206 0.5673 0.078 Uiso 1 1 calc R
C11 C 1.8491(4) -0.2252(5) 0.7627(4) 0.0812(16) Uani 1 1 d .
H11 H 1.9122 -0.2750 0.7650 0.097 Uiso 1 1 calc R
C12 C 1.7449(4) -0.2323(5) 0.6885(3) 0.0733(14) Uani 1 1 d .
H12A H 1.7380 -0.2856 0.6422 0.088 Uiso 1 1 calc R
C13 C 1.6507(4) -0.1593(4) 0.6836(3) 0.0589(11) Uani 1 1 d .
C14 C 1.6657(5) -0.0817(4) 0.7531(3) 0.0717(13) Uani 1 1 d .
H14 H 1.6043 -0.0304 0.7520 0.086 Uiso 1 1 calc R
C15 C 1.7744(5) -0.0815(5) 0.8252(3) 0.0827(16) Uani 1 1 d .
H15 H 1.7841 -0.0286 0.8722 0.099 Uiso 1 1 calc R
N21 N 0.3688(4) -0.2351(4) -0.0895(3) 0.0732(12) Uani 1 1 d .
N22 N 0.6714(3) -0.1054(3) 0.1181(2) 0.0609(10) Uani 1 1 d .
H22 H 0.6751 -0.1261 0.1725 0.073 Uiso 1 1 calc R
C21 C 0.4460(4) -0.1660(4) -0.1090(3) 0.0669(12) Uani 1 1 d .
H21 H 0.4304 -0.1469 -0.1703 0.080 Uiso 1 1 calc R
C22 C 0.5479(4) -0.1200(4) -0.0456(3) 0.0651(12) Uani 1 1 d .
H22A H 0.5981 -0.0709 -0.0641 0.078 Uiso 1 1 calc R
C23 C 0.5743(4) -0.1480(4) 0.0459(3) 0.0562(11) Uani 1 1 d .
C24 C 0.4939(5) -0.2214(5) 0.0676(3) 0.0760(14) Uani 1 1 d .
H24 H 0.5075 -0.2431 0.1282 0.091 Uiso 1 1 calc R
C25 C 0.3949(5) -0.2611(5) -0.0010(4) 0.0864(17) Uani 1 1 d .
H25 H 0.3421 -0.3095 0.0152 0.104 Uiso 1 1 calc R
C1 C 1.4422(4) -0.1086(5) 0.5849(4) 0.0779(15) Uani 1 1 d .
C2 C 1.3497(5) -0.1425(5) 0.4954(4) 0.0851(16) Uani 1 1 d .
H2A H 1.3249 -0.2208 0.5006 0.102 Uiso 1 1 calc .
H2B H 1.3879 -0.1413 0.4483 0.102 Uiso 1 1 calc .
C3 C 1.2387(4) -0.0686(4) 0.4641(3) 0.0701(13) Uani 1 1 d .
H3A H 1.2627 0.0109 0.4627 0.084 Uiso 1 1 calc .
H3B H 1.1955 -0.0747 0.5079 0.084 Uiso 1 1 calc .
C4 C 1.1547(4) -0.1028(4) 0.3695(3) 0.0669(12) Uani 1 1 d .
H4A H 1.1987 -0.0961 0.3264 0.080 Uiso 1 1 calc .
H4B H 1.1330 -0.1828 0.3713 0.080 Uiso 1 1 calc .
C5 C 1.0404(4) -0.0337(4) 0.3339(3) 0.0642(12) Uani 1 1 d .
H5A H 1.0617 0.0462 0.3309 0.077 Uiso 1 1 calc .
H5B H 0.9965 -0.0396 0.3772 0.077 Uiso 1 1 calc .
C6 C 0.9578(4) -0.0707(4) 0.2402(3) 0.0652(12) Uani 1 1 d .
H6A H 0.9317 -0.1490 0.2438 0.078 Uiso 1 1 calc .
H6B H 1.0028 -0.0695 0.1974 0.078 Uiso 1 1 calc .
C7 C 0.8463(4) 0.0062(4) 0.2034(3) 0.0684(13) Uani 1 1 d .
H7A H 0.8038 0.0085 0.2477 0.082 Uiso 1 1 calc .
H7B H 0.8722 0.0836 0.1962 0.082 Uiso 1 1 calc .
C8 C 0.7607(4) -0.0352(4) 0.1123(3) 0.0655(12) Uani 1 1 d .
O1 O 1.4260(4) -0.0345(4) 0.6348(3) 0.134(2) 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
C15 N11 C11 116.4(4)
C1 N12 C13 129.0(4)
N11 C11 C12 124.0(5)
C11 C12 C13 118.9(5)
C14 C13 C12 118.3(4)
C14 C13 N12 124.7(4)
C12 C13 N12 117.0(4)
C13 C14 C15 118.4(5)
N11 C15 C14 124.0(5)
C21 N21 C25 115.6(4)
C8 N22 C23 127.4(4)
N21 C21 C22 125.1(5)
C21 C22 C23 118.8(5)
C22 C23 N22 125.4(4)
C22 C23 C24 116.8(4)
N22 C23 C24 117.7(4)
C25 C24 C23 119.3(5)
N21 C25 C24 124.4(5)
O1 C1 N12 122.3(5)
O1 C1 C2 123.8(5)
N12 C1 C2 113.9(4)
C1 C2 C3 115.4(4)
C2 C3 C4 112.0(4)
C5 C4 C3 115.2(4)
C4 C5 C6 114.0(4)
C5 C6 C7 112.6(4)
C8 C7 C6 112.3(4)
O8 C8 N22 123.2(4)
O8 C8 C7 121.9(4)
N22 C8 C7 114.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O8 C8 1.226(6)
N11 C15 1.321(7)
N11 C11 1.325(7)
N12 C1 1.348(6)
N12 C13 1.400(5)
C11 C12 1.370(6)
C12 C13 1.374(7)
C13 C14 1.368(6)
C14 C15 1.384(7)
N21 C21 1.316(6)
N21 C25 1.331(6)
N22 C8 1.352(6)
N22 C23 1.392(5)
C21 C22 1.375(6)
C22 C23 1.381(6)
C23 C24 1.391(6)
C24 C25 1.364(7)
C1 O1 1.212(6)
C1 C2 1.498(7)
C2 C3 1.499(7)
C3 C4 1.517(6)
C4 C5 1.500(6)
C5 C6 1.511(6)
C6 C7 1.528(6)
C7 C8 1.509(6)
