#------------------------------------------------------------------------------
#$Date: 2020-06-25 01:52:05 +0300 (Thu, 25 Jun 2020) $
#$Revision: 253421 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/50/4135091.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_4135091
loop_
_publ_author_name
'Levesque, Alexandre'
'Maris, Thierry'
'Wuest, James D.'
_publ_section_title
;
 ROY Reclaims Its Crown: New Ways to Increase Polymorphic Diversity.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c04434
_journal_year                    2020
_chemical_formula_moiety         'C12 H9 N3 O3'
_chemical_formula_sum            'C12 H9 N3 O3'
_chemical_formula_weight         243.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.3240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.2603(10)
_cell_length_b                   6.8371(3)
_cell_length_c                   14.6629(6)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.082
_cell_measurement_theta_min      4.109
_cell_volume                     2157.11(16)
_computing_cell_refinement
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_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
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26079
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.089
_diffrn_reflns_theta_min         4.109
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_exptl_absorpt_coefficient_mu    0.933
_exptl_absorpt_correction_T_max  0.3841
_exptl_absorpt_correction_T_min  0.2576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1304 before and 0.0504 after correction. The Ratio of minimum to maximum transmission is 0.6707. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       Block
_exptl_crystal_F_000             1008
_exptl_crystal_recrystallization_method 'crystallized from EtOAc'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.00046(13)
_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   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0368
_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)+(0.0505P)²+2.5036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1976
_reflns_number_total             2003
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c04434_si_005.cif
_cod_data_source_block           FuROY_OY
_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/rss-feeds/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               4135091
_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   0.888
_shelx_estimated_absorpt_t_min   0.787
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C23(H23)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_olex2_date_sample_data_collection 2019-03-25
_olex2_date_sample_submission    2019-03-22
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_original_sample_id FuROY-OR
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.39910(4) 0.63875(14) 0.39922(7) 0.0239(3) Uani 1 1 d . . . . .
O21 O 0.20701(5) 0.59520(16) 0.44283(8) 0.0289(3) Uani 1 1 d . . . . .
O22 O 0.13724(5) 0.37598(17) 0.37368(8) 0.0327(3) Uani 1 1 d . . . . .
N1 N 0.32190(5) 0.55059(19) 0.45841(9) 0.0243(3) Uani 1 1 d . . . . .
H1 H 0.2983(9) 0.620(3) 0.4757(14) 0.036 Uiso 1 1 d R . . . .
N2 N 0.19087(5) 0.43462(18) 0.40156(8) 0.0240(3) Uani 1 1 d . . . . .
N3 N 0.42037(6) 0.7015(2) 0.73236(9) 0.0330(3) Uani 1 1 d . . . . .
C2 C 0.42212(6) 0.6995(2) 0.65505(11) 0.0251(3) Uani 1 1 d . . . . .
C3 C 0.48613(7) 0.7543(2) 0.36099(11) 0.0285(3) Uani 1 1 d . . . . .
H3A H 0.487742 0.631688 0.330174 0.043 Uiso 1 1 calc GR . . . .
H3B H 0.527501 0.804512 0.393281 0.043 Uiso 1 1 calc GR . . . .
H3C H 0.461742 0.845804 0.311844 0.043 Uiso 1 1 calc GR . . . .
C11 C 0.29982(6) 0.3737(2) 0.41331(9) 0.0222(3) Uani 1 1 d . . . . .
C12 C 0.23753(6) 0.3118(2) 0.38635(10) 0.0227(3) Uani 1 1 d . . . . .
C13 C 0.21723(7) 0.1297(2) 0.34266(10) 0.0257(3) Uani 1 1 d . . . . .
H13 H 0.175948 0.092949 0.325401 0.031 Uiso 1 1 calc R . . . .
C14 C 0.25831(7) 0.0049(2) 0.32516(10) 0.0274(3) Uani 1 1 d . . . . .
H14 H 0.245260 -0.117567 0.297417 0.033 Uiso 1 1 calc R . . . .
C15 C 0.31959(7) 0.0640(2) 0.34943(10) 0.0272(3) Uani 1 1 d . . . . .
H15 H 0.347291 -0.019120 0.336642 0.033 Uiso 1 1 calc R . . . .
C16 C 0.33985(6) 0.2434(2) 0.39207(10) 0.0255(3) Uani 1 1 d . . . . .
H16 H 0.381005 0.279351 0.407202 0.031 Uiso 1 1 calc R . . . .
C21 C 0.38074(6) 0.6215(2) 0.47672(10) 0.0232(3) Uani 1 1 d . . . . .
C22 C 0.42516(6) 0.6959(2) 0.55955(10) 0.0226(3) Uani 1 1 d . . . . .
C23 C 0.47460(6) 0.7637(2) 0.53156(10) 0.0245(3) Uani 1 1 d . . . . .
H23 H 0.511381 0.822794 0.572423 0.029 Uiso 1 1 calc R . . . .
C24 C 0.45741(6) 0.7250(2) 0.43464(11) 0.0242(3) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C21 O1 C24 107.24(10) . . ?
C11 N1 H1 118.3(14) . . ?
C21 N1 H1 117.4(14) . . ?
C21 N1 C11 124.23(12) . . ?
O21 N2 C12 118.70(11) . . ?
O22 N2 O21 122.28(12) . . ?
O22 N2 C12 119.01(12) . . ?
N3 C2 C22 179.19(15) . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C24 C3 H3A 109.5 . . ?
C24 C3 H3B 109.5 . . ?
C24 C3 H3C 109.5 . . ?
N1 C11 C12 123.44(13) . . ?
N1 C11 C16 120.26(12) . . ?
C16 C11 C12 116.30(13) . . ?
C11 C12 N2 121.97(13) . . ?
C13 C12 N2 116.27(12) . . ?
C13 C12 C11 121.76(13) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.02(13) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.25(14) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.04(14) . . ?
C16 C15 H15 119.5 . . ?
C11 C16 H16 119.2 . . ?
C15 C16 C11 121.60(13) . . ?
C15 C16 H16 119.2 . . ?
O1 C21 N1 118.06(12) . . ?
C22 C21 O1 109.89(12) . . ?
C22 C21 N1 131.83(13) . . ?
C2 C22 C23 128.13(13) . . ?
C21 C22 C2 125.33(13) . . ?
C21 C22 C23 106.53(12) . . ?
C22 C23 H23 126.6 . . ?
C24 C23 C22 106.79(13) . . ?
C24 C23 H23 126.6 . . ?
O1 C24 C3 115.58(12) . . ?
C23 C24 O1 109.54(12) . . ?
C23 C24 C3 134.88(14) . . ?
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 C21 1.3624(17) . ?
O1 C24 1.3864(17) . ?
O21 N2 1.2409(16) . ?
O22 N2 1.2234(15) . ?
N1 H1 0.83(2) . ?
N1 C11 1.3807(19) . ?
N1 C21 1.3789(18) . ?
N2 C12 1.4548(18) . ?
N3 C2 1.1497(19) . ?
C2 C22 1.4289(19) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C3 C24 1.4836(19) . ?
C11 C12 1.4139(19) . ?
C11 C16 1.406(2) . ?
C12 C13 1.398(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.391(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(2) . ?
C16 H16 0.9300 . ?
C21 C22 1.359(2) . ?
C22 C23 1.4367(19) . ?
C23 H23 0.9300 . ?
C23 C24 1.348(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 O21 0.83(2) 2.00(2) 2.6120(15) 129.9(17) . yes
N1 H1 O21 0.83(2) 2.31(2) 3.0256(16) 143.6(17) 7_566 yes
C16 H16 O1 0.93 2.50 3.0179(18) 115.1 . 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
O1 C21 C22 C2 -178.93(13) . . . . ?
O1 C21 C22 C23 -0.13(16) . . . . ?
O21 N2 C12 C11 -2.76(19) . . . . ?
O21 N2 C12 C13 177.84(11) . . . . ?
O22 N2 C12 C11 177.53(12) . . . . ?
O22 N2 C12 C13 -1.86(18) . . . . ?
N1 C11 C12 N2 2.0(2) . . . . ?
N1 C11 C12 C13 -178.64(12) . . . . ?
N1 C11 C16 C15 178.35(13) . . . . ?
N1 C21 C22 C2 6.8(3) . . . . ?
N1 C21 C22 C23 -174.44(15) . . . . ?
N2 C12 C13 C14 179.66(12) . . . . ?
C2 C22 C23 C24 178.28(14) . . . . ?
C11 N1 C21 O1 55.73(19) . . . . ?
C11 N1 C21 C22 -130.33(17) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C12 C11 C16 C15 -1.4(2) . . . . ?
C12 C13 C14 C15 -1.4(2) . . . . ?
C13 C14 C15 C16 1.1(2) . . . . ?
C14 C15 C16 C11 0.3(2) . . . . ?
C16 C11 C12 N2 -178.24(12) . . . . ?
C16 C11 C12 C13 1.12(19) . . . . ?
C21 O1 C24 C3 179.22(12) . . . . ?
C21 O1 C24 C23 -0.99(15) . . . . ?
C21 N1 C11 C12 -173.55(13) . . . . ?
C21 N1 C11 C16 6.7(2) . . . . ?
C21 C22 C23 C24 -0.48(16) . . . . ?
C22 C23 C24 O1 0.90(16) . . . . ?
C22 C23 C24 C3 -179.36(16) . . . . ?
C24 O1 C21 N1 175.87(12) . . . . ?
C24 O1 C21 C22 0.68(15) . . . . ?
