#------------------------------------------------------------------------------
#$Date: 2025-08-21 02:19:08 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301842 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/44/4504452.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_4504452
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
 \b-Sheet, and Two-Dimensional Layers
;
_journal_issue                   12
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              2788
_journal_paper_doi               10.1021/cg0706417
_journal_volume                  7
_journal_year                    2007
_chemical_formula_sum            'C14 H14 N4 O2'
_chemical_formula_weight         270.29
_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                 102.05(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.7370(15)
_cell_length_b                   8.1290(16)
_cell_length_c                   10.546(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      8
_cell_volume                     648.7(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       \w-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  0.0067
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1225
_diffrn_reflns_theta_full        24.95
_diffrn_reflns_theta_max         24.95
_diffrn_reflns_theta_min         2.99
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0461
_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/[\s^2^(Fo^2^)+(0.0652P)^2^+0.3775P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                897
_reflns_number_total             1137
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0706417-file002.cif
_cod_data_source_block           4a
_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               4504452
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
N1 N -0.2291(2) 0.1501(3) -0.18486(15) 0.0472(5) Uani 1 1 d .
N2 N 0.1576(2) 0.3377(2) 0.03070(14) 0.0371(4) Uani 1 1 d .
H2 H 0.1855 0.3564 0.1127 0.045 Uiso 1 1 calc R
O6 O 0.2462(3) 0.3850(3) -0.15746(15) 0.0844(8) Uani 1 1 d .
C1 C -0.0018(2) 0.2541(2) -0.01342(18) 0.0341(5) Uani 1 1 d .
C2 C -0.0793(3) 0.2328(3) -0.14400(19) 0.0426(5) Uani 1 1 d .
H2A H -0.0236 0.2787 -0.2057 0.051 Uiso 1 1 calc R
C3 C -0.3080(3) 0.0842(3) -0.0963(2) 0.0503(6) Uani 1 1 d .
H3 H -0.4119 0.0250 -0.1240 0.060 Uiso 1 1 calc R
C4 C -0.2420(3) 0.1003(3) 0.0345(2) 0.0506(6) Uani 1 1 d .
H4 H -0.3008 0.0532 0.0940 0.061 Uiso 1 1 calc R
C5 C -0.0881(3) 0.1868(3) 0.07647(18) 0.0410(5) Uani 1 1 d .
H5 H -0.0424 0.2000 0.1647 0.049 Uiso 1 1 calc R
C6 C 0.2729(3) 0.3928(3) -0.03984(19) 0.0440(5) Uani 1 1 d .
C7 C 0.4396(3) 0.4653(3) 0.04011(19) 0.0474(6) Uani 1 1 d .
H7A H 0.4082 0.5517 0.0946 0.057 Uiso 1 1 calc .
H7B H 0.5020 0.3806 0.0965 0.057 Uiso 1 1 calc .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0412(10) 0.0655(13) 0.0323(9) -0.0037(8) 0.0014(7) -0.0046(8)
N2 0.0362(9) 0.0509(10) 0.0241(7) -0.0030(7) 0.0060(6) -0.0070(7)
O6 0.0782(13) 0.147(2) 0.0316(9) -0.0151(10) 0.0191(8) -0.0572(13)
C1 0.0347(9) 0.0414(11) 0.0256(9) -0.0003(8) 0.0048(7) 0.0016(8)
C2 0.0424(11) 0.0571(13) 0.0277(10) 0.0021(9) 0.0061(8) -0.0067(10)
C3 0.0380(11) 0.0678(15) 0.0450(12) -0.0064(11) 0.0081(9) -0.0112(11)
C4 0.0446(12) 0.0695(16) 0.0401(11) 0.0017(11) 0.0144(9) -0.0124(11)
C5 0.0394(11) 0.0562(13) 0.0269(9) 0.0002(9) 0.0053(8) -0.0036(9)
C6 0.0465(12) 0.0572(13) 0.0299(10) -0.0040(9) 0.0114(8) -0.0108(10)
C7 0.0441(12) 0.0631(14) 0.0365(11) -0.0033(10) 0.0118(9) -0.0137(10)
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
C3 N1 C2 118.17(17) .
C6 N2 C1 127.92(16) .
C5 C1 N2 118.86(16) .
C5 C1 C2 117.34(18) .
N2 C1 C2 123.79(17) .
N1 C2 C1 123.26(19) .
N1 C3 C4 122.6(2) .
C3 C4 C5 119.15(19) .
C4 C5 C1 119.51(18) .
O6 C6 N2 123.62(19) .
O6 C6 C7 122.32(19) .
N2 C6 C7 114.07(16) .
C7 C7 C6 113.2(2) 3_665
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C3 1.330(3) .
N1 C2 1.332(3) .
N2 C6 1.351(2) .
N2 C1 1.400(3) .
O6 C6 1.216(2) .
C1 C5 1.381(3) .
C1 C2 1.393(3) .
C3 C4 1.374(3) .
C4 C5 1.374(3) .
C6 C7 1.506(3) .
C7 C7 1.497(4) 3_665
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 897084
