#------------------------------------------------------------------------------
#$Date: 2021-03-04 03:28:18 +0200 (Thu, 04 Mar 2021) $
#$Revision: 262431 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/08/1560808.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_1560808
loop_
_publ_author_name
'Goodlett, Dustin W.'
'Sindt, Ammon J.'
'Hossain, Muhammad Saddam'
'Merugu, Rajkumar'
'Smith, Mark D.'
'Garashchuk, Sophya'
'Gudmundsdottir, Anna D.'
'Shimizu, Linda S.'
_publ_section_title
;
 From Incident Light to Persistent and Regenerable Radicals of
 Urea-Assembled Benzophenone Frameworks: A Structural Investigation.
;
_journal_issue                   6
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              1336
_journal_page_last               1344
_journal_paper_doi               10.1021/acs.jpca.0c08953
_journal_volume                  125
_journal_year                    2021
_chemical_formula_moiety         'C32 H28 N4 O4'
_chemical_formula_sum            'C32 H28 N4 O4'
_chemical_formula_weight         532.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.848(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.5196(2)
_cell_length_b                   37.0928(18)
_cell_length_c                   7.9294(4)
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.064
_cell_measurement_theta_min      2.196
_cell_volume                     1319.84(11)
_computing_cell_refinement       'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0870
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            41103
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.085
_diffrn_reflns_theta_max         25.087
_diffrn_reflns_theta_min         2.196
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.6193
_exptl_absorpt_correction_T_min  0.5638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1455 before and 0.0756 after correction.
The Ratio of minimum to maximum transmission is 0.9104.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0163(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0278P)²+1.1207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1075
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1799
_reflns_number_total             2361
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp0c08953_si_002.cif
_cod_data_source_block           dg35bpdm
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               1560808
_shelx_shelxl_version_number     2018/3
_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   0.998
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4765(3) 0.47441(4) 0.22864(19) 0.0237(4) Uani 1 1 d . . . . .
O2 O 0.9541(4) 0.31402(4) 0.5614(2) 0.0385(5) Uani 1 1 d . . . . .
N1 N 0.0455(4) 0.50624(5) 0.2303(2) 0.0212(5) Uani 1 1 d . . . . .
H1 H -0.148(6) 0.5040(6) 0.231(3) 0.023(6) Uiso 1 1 d . . . . .
N2 N 0.0739(5) 0.44758(5) 0.3201(2) 0.0212(5) Uani 1 1 d . . . . .
H2 H -0.121(6) 0.4489(7) 0.320(3) 0.031(7) Uiso 1 1 d . . . . .
C1 C 0.2119(5) 0.47607(6) 0.2571(3) 0.0190(5) Uani 1 1 d . . . . .
C2 C 0.2160(5) 0.41254(6) 0.3390(3) 0.0226(5) Uani 1 1 d . . . . .
H2A H 0.317(5) 0.4074(6) 0.234(3) 0.025(6) Uiso 1 1 d . . . . .
H2B H 0.054(5) 0.3939(6) 0.342(3) 0.025(6) Uiso 1 1 d . . . . .
C3 C 0.4430(5) 0.40801(6) 0.4944(3) 0.0210(5) Uani 1 1 d . . . . .
C4 C 0.5352(5) 0.43641(6) 0.6017(3) 0.0197(5) Uani 1 1 d . . . . .
H4 H 0.456(5) 0.4604(6) 0.578(3) 0.015(6) Uiso 1 1 d . . . . .
C5 C 0.7535(5) 0.43144(6) 0.7402(3) 0.0202(5) Uani 1 1 d . . . . .
C6 C 0.8755(5) 0.39749(6) 0.7712(3) 0.0212(5) Uani 1 1 d . . . . .
H6 H 1.040(5) 0.3946(6) 0.868(3) 0.027(6) Uiso 1 1 d . . . . .
C7 C 0.7829(5) 0.36848(6) 0.6655(3) 0.0225(5) Uani 1 1 d . . . . .
C8 C 0.5678(5) 0.37411(6) 0.5272(3) 0.0216(5) Uani 1 1 d . . . . .
H8 H 0.511(5) 0.3537(6) 0.451(3) 0.016(6) Uiso 1 1 d . . . . .
C9 C 0.9241(5) 0.33199(6) 0.6873(3) 0.0261(6) Uani 1 1 d . . . . .
C10 C 1.0292(5) 0.31760(6) 0.8600(3) 0.0265(6) Uani 1 1 d . . . . .
C11 C 0.9195(6) 0.32981(7) 1.0061(3) 0.0312(6) Uani 1 1 d . . . . .
H11 H 0.760(5) 0.3492(6) 1.000(3) 0.027(6) Uiso 1 1 d . . . . .
C12 C 1.0153(7) 0.31418(7) 1.1624(3) 0.0377(7) Uani 1 1 d . . . . .
H12 H 0.932(5) 0.3223(6) 1.262(3) 0.033(7) Uiso 1 1 d . . . . .
C13 C 1.2189(7) 0.28625(7) 1.1721(4) 0.0421(8) Uani 1 1 d . . . . .
H13 H 1.300(6) 0.2752(7) 1.284(4) 0.052(8) Uiso 1 1 d . . . . .
C14 C 1.3251(7) 0.27355(7) 1.0273(4) 0.0403(7) Uani 1 1 d . . . . .
H14 H 1.478(6) 0.2541(8) 1.035(3) 0.048(8) Uiso 1 1 d . . . . .
C15 C 1.2325(6) 0.28904(7) 0.8714(3) 0.0323(6) Uani 1 1 d . . . . .
H15 H 1.308(6) 0.2804(6) 0.766(3) 0.036(7) Uiso 1 1 d . . . . .
C16 C 0.8532(6) 0.46241(6) 0.8572(3) 0.0226(5) Uani 1 1 d . . . . .
H16A H 0.683(6) 0.4698(6) 0.921(3) 0.028(6) Uiso 1 1 d . . . . .
H16B H 1.029(5) 0.4543(6) 0.942(3) 0.027(6) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 117.2(15) . . ?
C1 N1 C16 122.4(2) . 3_666 ?
C16 N1 H1 116.7(15) 3_666 . ?
C1 N2 H2 117.2(16) . . ?
C1 N2 C2 121.4(2) . . ?
C2 N2 H2 118.8(16) . . ?
O1 C1 N1 122.8(2) . . ?
O1 C1 N2 121.6(2) . . ?
N1 C1 N2 115.6(2) . . ?
N2 C2 H2A 108.7(13) . . ?
N2 C2 H2B 107.7(13) . . ?
N2 C2 C3 115.60(19) . . ?
H2A C2 H2B 106.6(18) . . ?
C3 C2 H2A 108.7(13) . . ?
C3 C2 H2B 109.0(13) . . ?
C4 C3 C2 122.6(2) . . ?
C4 C3 C8 119.1(2) . . ?
C8 C3 C2 118.2(2) . . ?
C3 C4 H4 120.1(12) . . ?
C3 C4 C5 120.9(2) . . ?
C5 C4 H4 118.8(12) . . ?
C4 C5 C16 120.8(2) . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 C16 119.9(2) . . ?
C5 C6 H6 118.4(13) . . ?
C5 C6 C7 120.6(2) . . ?
C7 C6 H6 120.9(13) . . ?
C6 C7 C9 122.2(2) . . ?
C8 C7 C6 119.2(2) . . ?
C8 C7 C9 118.3(2) . . ?
C3 C8 C7 120.9(2) . . ?
C3 C8 H8 120.6(12) . . ?
C7 C8 H8 118.5(12) . . ?
O2 C9 C7 119.1(2) . . ?
O2 C9 C10 120.0(2) . . ?
C10 C9 C7 120.9(2) . . ?
C11 C10 C9 122.8(2) . . ?
C11 C10 C15 119.4(2) . . ?
C15 C10 C9 117.7(2) . . ?
C10 C11 H11 120.8(13) . . ?
C10 C11 C12 120.2(3) . . ?
C12 C11 H11 118.9(14) . . ?
C11 C12 H12 119.6(15) . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.6(15) . . ?
C12 C13 H13 121.5(16) . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 118.1(16) . . ?
C13 C14 H14 120.1(16) . . ?
C13 C14 C15 120.3(3) . . ?
C15 C14 H14 119.5(16) . . ?
C10 C15 H15 118.7(14) . . ?
C14 C15 C10 120.0(3) . . ?
C14 C15 H15 121.4(15) . . ?
N1 C16 C5 113.76(18) 3_666 . ?
N1 C16 H16A 108.9(13) 3_666 . ?
N1 C16 H16B 106.6(13) 3_666 . ?
C5 C16 H16A 108.8(14) . . ?
C5 C16 H16B 109.5(13) . . ?
H16A C16 H16B 109.3(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.245(3) . ?
O2 C9 1.221(3) . ?
N1 H1 0.88(3) . ?
N1 C1 1.351(3) . ?
N1 C16 1.455(3) 3_666 ?
N2 H2 0.88(3) . ?
N2 C1 1.353(3) . ?
N2 C2 1.449(3) . ?
C2 H2A 1.02(2) . ?
C2 H2B 1.01(2) . ?
C2 C3 1.516(3) . ?
C3 C4 1.386(3) . ?
C3 C8 1.390(3) . ?
C4 H4 0.97(2) . ?
C4 C5 1.399(3) . ?
C5 C6 1.385(3) . ?
C5 C16 1.511(3) . ?
C6 H6 1.01(2) . ?
C6 C7 1.397(3) . ?
C7 C8 1.392(3) . ?
C7 C9 1.498(3) . ?
C8 H8 0.98(2) . ?
C9 C10 1.493(3) . ?
C10 C11 1.389(3) . ?
C10 C15 1.398(3) . ?
C11 H11 1.02(2) . ?
C11 C12 1.390(4) . ?
C12 H12 0.96(3) . ?
C12 C13 1.382(4) . ?
C13 H13 1.01(3) . ?
C13 C14 1.379(4) . ?
C14 H14 1.00(3) . ?
C14 C15 1.382(4) . ?
C15 H15 0.99(3) . ?
C16 H16A 1.01(3) . ?
C16 H16B 1.02(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.88(3) 2.02(2) 2.829(2) 152(2) 1_455 yes
N2 H2 O1 0.88(3) 2.10(3) 2.888(3) 148(2) 1_455 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C9 C10 C11 -157.8(2) . . . . ?
O2 C9 C10 C15 18.0(3) . . . . ?
N2 C2 C3 C4 -7.0(3) . . . . ?
N2 C2 C3 C8 174.5(2) . . . . ?
C1 N2 C2 C3 79.9(3) . . . . ?
C2 N2 C1 O1 -7.2(3) . . . . ?
C2 N2 C1 N1 173.78(19) . . . . ?
C2 C3 C4 C5 -177.5(2) . . . . ?
C2 C3 C8 C7 178.4(2) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C3 C4 C5 C16 -179.9(2) . . . . ?
C4 C3 C8 C7 -0.1(3) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C4 C5 C16 N1 -54.8(3) . . . 3_666 ?
C5 C6 C7 C8 0.6(3) . . . . ?
C5 C6 C7 C9 175.6(2) . . . . ?
C6 C5 C16 N1 126.2(2) . . . 3_666 ?
C6 C7 C8 C3 -0.6(3) . . . . ?
C6 C7 C9 O2 -143.9(2) . . . . ?
C6 C7 C9 C10 35.8(3) . . . . ?
C7 C9 C10 C11 22.5(4) . . . . ?
C7 C9 C10 C15 -161.7(2) . . . . ?
C8 C3 C4 C5 0.9(3) . . . . ?
C8 C7 C9 O2 31.2(3) . . . . ?
C8 C7 C9 C10 -149.1(2) . . . . ?
C9 C7 C8 C3 -175.8(2) . . . . ?
C9 C10 C11 C12 176.9(2) . . . . ?
C9 C10 C15 C14 -176.7(2) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C11 C10 C15 C14 -0.8(4) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C12 C13 C14 C15 1.0(4) . . . . ?
C13 C14 C15 C10 -0.3(4) . . . . ?
C15 C10 C11 C12 1.2(4) . . . . ?
C16 N1 C1 O1 9.2(3) 3_666 . . . ?
C16 N1 C1 N2 -171.80(18) 3_666 . . . ?
C16 C5 C6 C7 179.2(2) . . . . ?
