#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/22/1552293.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1552293
loop_
_publ_author_name
'Oburn, Shalisa M.'
'Sinnwell, Michael A.'
'Ericson, Devin P.'
'Reinheimer, Eric W.'
'Proserpio, Davide M.'
'Groeneman, Ryan H.'
'MacGillivray, Leonard'
_publ_section_title
;
 Diversifying molecular and topological space via a supramolecular
 solid-state synthesis: a purely organic mok net sustained by hydrogen
 bonds
;
_journal_issue                   6
_journal_name_full               IUCrJ
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052252519011382
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C15 H13 N O2'
_chemical_formula_sum            'C15 H13 N O2'
_chemical_formula_weight         239.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.5366(11)
_cell_length_b                   7.4255(7)
_cell_length_c                   31.091(3)
_cell_measurement_reflns_used    5803
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      22.66
_cell_measurement_theta_min      2.335
_cell_volume                     2432.5(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_collection       'Collect (Hooft, 1998)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      190(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            30658
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.245
_diffrn_reflns_theta_max         25.245
_diffrn_reflns_theta_min         2.335
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0790 before and 0.0685 after correction.
The Ratio of minimum to maximum transmission is 0.9038.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0899P)²+1.5926P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.1800
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1517
_reflns_number_total             2205
_reflns_threshold_expression     'I > 2σ(I)'
_publcif_datablock.id            {1f021776-a0bb-40bf-a7e1-5cadfb2d756f}
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_cod_data_source_file            yc5020.cif
_cod_data_source_block           mcg16122
_cod_database_code               1552293
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
?
;
_shelx_shelxl_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
O2 O 0.55896(19) 0.5816(3) 0.61256(6) 0.0375(6) Uani 1 1 d
O1 O 0.71992(19) 0.7630(3) 0.59268(6) 0.0422(6) Uani 1 1 d
N1 N 0.6330(3) 0.4960(4) 0.95677(8) 0.0459(7) Uani 1 1 d
C8 C 0.6347(2) 0.5899(3) 0.74464(9) 0.0265(6) Uani 1 1 d
C7 C 0.6587(3) 0.5732(4) 0.79076(9) 0.0289(7) Uani 1 1 d
C11 C 0.5237(3) 0.6678(4) 0.72741(10) 0.0296(7) Uani 1 1 d
C5 C 0.6071(3) 0.5865(4) 0.86888(9) 0.0302(7) Uani 1 1 d
C12 C 0.5024(3) 0.6703(4) 0.68374(10) 0.0312(7) Uani 1 1 d
C9 C 0.7223(3) 0.5178(4) 0.71563(9) 0.0308(7) Uani 1 1 d
C6 C 0.5869(3) 0.6275(4) 0.82330(10) 0.0325(7) Uani 1 1 d
C13 C 0.5901(3) 0.5941(4) 0.65610(9) 0.0295(7) Uani 1 1 d
C10 C 0.7018(3) 0.5193(4) 0.67174(10) 0.0324(7) Uani 1 1 d
C14 C 0.6350(3) 0.6640(4) 0.58275(9) 0.0356(7) Uani 1 1 d
C4 C 0.5135(3) 0.6248(4) 0.89887(10) 0.0364(8) Uani 1 1 d
C2 C 0.7160(3) 0.5030(4) 0.88478(10) 0.0361(7) Uani 1 1 d
C3 C 0.5289(3) 0.5773(4) 0.94109(11) 0.0428(8) Uani 1 1 d
C1 C 0.7242(3) 0.4615(5) 0.92774(10) 0.0427(8) Uani 1 1 d
C15 C 0.5977(4) 0.6138(7) 0.53839(12) 0.0548(10) Uani 1 1 d
H7 H 0.736(3) 0.504(4) 0.7978(9) 0.036(8) Uiso 1 1 d
H1 H 0.804(3) 0.403(4) 0.9377(10) 0.052(10) Uiso 1 1 d
H3 H 0.464(3) 0.599(4) 0.9626(11) 0.055(10) Uiso 1 1 d
H6 H 0.514(3) 0.690(5) 0.8171(10) 0.053(10) Uiso 1 1 d
H4 H 0.437(3) 0.679(4) 0.8895(10) 0.045(9) Uiso 1 1 d
H2 H 0.783(3) 0.466(4) 0.8665(10) 0.045(9) Uiso 1 1 d
H12 H 0.422(3) 0.717(5) 0.6708(10) 0.056(10) Uiso 1 1 d
H9 H 0.804(3) 0.468(4) 0.7279(9) 0.032(8) Uiso 1 1 d
H11 H 0.464(3) 0.709(4) 0.7476(11) 0.051(10) Uiso 1 1 d
H10 H 0.757(4) 0.468(4) 0.6517(10) 0.053(10) Uiso 1 1 d
H15A H 0.614(6) 0.495(9) 0.530(2) 0.16(3) Uiso 1 1 d
H15B H 0.639(5) 0.691(7) 0.5180(16) 0.113(19) Uiso 1 1 d
H15C H 0.507(6) 0.607(7) 0.5367(17) 0.12(2) Uiso 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
C14 O2 C13 119.3(2)
C3 N1 C1 115.2(3)
C11 C8 C7 123.4(3)
C9 C8 C7 119.1(3)
C9 C8 C11 117.4(3)
C8 C7 H7 113.9(16)
C6 C7 C8 128.6(3)
C6 C7 H7 117.3(16)
C8 C11 H11 116(2)
C12 C11 C8 121.0(3)
C12 C11 H11 123(2)
C4 C5 C6 120.3(3)
C4 C5 C2 116.0(3)
C2 C5 C6 123.7(3)
C11 C12 C13 119.9(3)
C11 C12 H12 122.5(19)
C13 C12 H12 117.4(19)
C8 C9 H9 117.2(16)
C10 C9 C8 122.1(3)
C10 C9 H9 120.7(16)
C7 C6 C5 126.3(3)
C7 C6 H6 118(2)
C5 C6 H6 115(2)
C12 C13 O2 118.2(2)
C12 C13 C10 120.8(3)
C10 C13 O2 120.8(2)
C9 C10 C13 118.8(3)
C9 C10 H10 124(2)
C13 C10 H10 117(2)
O2 C14 C15 111.2(3)
O1 C14 O2 122.4(3)
O1 C14 C15 126.3(3)
C5 C4 H4 119.1(19)
C3 C4 C5 120.5(3)
C3 C4 H4 120.4(19)
C5 C2 H2 122.0(19)
C1 C2 C5 119.8(3)
C1 C2 H2 118.1(19)
N1 C3 C4 124.1(3)
N1 C3 H3 114(2)
C4 C3 H3 122(2)
N1 C1 C2 124.4(3)
N1 C1 H1 118.7(19)
C2 C1 H1 116.8(19)
C14 C15 H15A 117(4)
C14 C15 H15B 110(3)
C14 C15 H15C 109(3)
H15A C15 H15B 107(5)
H15A C15 H15C 97(5)
H15B C15 H15C 116(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C13 1.396(3)
O2 C14 1.369(4)
O1 C14 1.198(3)
N1 C3 1.343(4)
N1 C1 1.343(4)
C8 C7 1.461(4)
C8 C11 1.411(4)
C8 C9 1.397(4)
C7 C6 1.326(4)
C7 H7 0.99(3)
C11 C12 1.376(4)
C11 H11 0.94(3)
C5 C6 1.465(4)
C5 C4 1.387(4)
C5 C2 1.394(4)
C12 C13 1.383(4)
C12 H12 1.00(4)
C9 C10 1.382(4)
C9 H9 1.01(3)
C6 H6 0.91(4)
C13 C10 1.388(4)
C10 H10 0.93(4)
C14 C15 1.482(5)
C4 C3 1.369(5)
C4 H4 0.95(3)
C2 C1 1.374(4)
C2 H2 0.95(3)
C3 H3 0.97(4)
C1 H1 1.00(3)
C15 H15A 0.93(7)
C15 H15B 0.96(5)
C15 H15C 0.96(6)
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
O2 C13 C10 C9 -173.2(2)
C8 C7 C6 C5 171.3(3)
C8 C11 C12 C13 0.6(4)
C8 C9 C10 C13 -0.3(4)
C7 C8 C11 C12 -176.0(2)
C7 C8 C9 C10 176.0(3)
C11 C8 C7 C6 -1.3(5)
C11 C8 C9 C10 -1.0(4)
C11 C12 C13 O2 173.1(2)
C11 C12 C13 C10 -1.9(4)
C5 C4 C3 N1 1.4(5)
C5 C2 C1 N1 -0.1(5)
C12 C13 C10 C9 1.7(4)
C9 C8 C7 C6 -178.1(3)
C9 C8 C11 C12 0.8(4)
C6 C5 C4 C3 176.2(3)
C6 C5 C2 C1 -176.7(3)
C13 O2 C14 O1 -8.3(4)
C13 O2 C14 C15 171.7(3)
C14 O2 C13 C12 121.2(3)
C14 O2 C13 C10 -63.8(3)
C4 C5 C6 C7 -168.7(3)
C4 C5 C2 C1 1.0(4)
C2 C5 C6 C7 8.9(5)
C2 C5 C4 C3 -1.6(4)
C3 N1 C1 C2 -0.2(5)
C1 N1 C3 C4 -0.4(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 6247672
