#------------------------------------------------------------------------------
#$Date: 2020-06-25 01:47:36 +0300 (Thu, 25 Jun 2020) $
#$Revision: 253411 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/50/4135081.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_4135081
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 O2.15 S0.85'
_chemical_formula_sum            'C12 H9 N3 O2.15 S0.85'
_chemical_formula_weight         256.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.736(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8643(3)
_cell_length_b                   18.7063(11)
_cell_length_c                   16.2605(10)
_cell_measurement_reflns_used    8853
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.903
_cell_measurement_theta_min      3.136
_cell_volume                     1174.08(14)
_computing_cell_refinement
;
SAINT (2013) V8.37A; 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) V8.37A; 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      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16472
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.015
_diffrn_reflns_theta_min         3.135
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    1.446
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1780 before and 0.0899 after correction. The Ratio of minimum to maximum transmission is 0.6625. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       needle
_exptl_crystal_F_000             531
_exptl_crystal_recrystallization_method 'crystallized from EtOH/Hexane'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2240
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0693
_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)+(0.0848P)²+1.0543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1815
_refine_ls_wR_factor_ref         0.1984
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1675
_reflns_number_total             2240
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c04434_si_013.cif
_cod_data_source_block           Mixed_ROY_ON_85_15
_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               4135081
_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   0.918
_shelx_estimated_absorpt_t_min   0.732
_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
2. Restrained distances
 N1-H1
 0.84 with sigma of 0.02
 C21-O1B
 1.34 with sigma of 0.005
 O1B-C24
 1.38 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(S1) = Uanis(O1B)
4. Others
 Sof(O1B)=1-FVAR(1)
 Sof(S1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C23(H23)
5.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_olex2_date_sample_data_collection 2019-03-11
_olex2_date_sample_submission    2019-03-06
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_original_sample_id 'JDW-AL-CoFUROY-1:1-F:F '
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S1 S 0.6695(4) 0.39903(7) 0.57056(6) 0.0627(5) Uani 0.853(6) 1 d . . P A 1
O21 O 0.9216(9) 0.31235(13) 0.86973(15) 0.0787(9) Uani 1 1 d . . . . .
O22 O 0.9961(8) 0.38435(14) 0.97214(14) 0.0763(8) Uani 1 1 d . . . . .
N1 N 0.6237(9) 0.35563(14) 0.73108(15) 0.0585(8) Uani 1 1 d D . . . .
N2 N 0.8801(9) 0.37157(15) 0.90180(16) 0.0609(8) Uani 1 1 d . . . . .
N3 N 0.1015(10) 0.19405(17) 0.7150(2) 0.0747(9) Uani 1 1 d . . . . .
C11 C 0.5705(10) 0.41785(17) 0.77423(19) 0.0539(8) Uani 1 1 d . . . . .
C12 C 0.6933(9) 0.42704(17) 0.85674(18) 0.0530(8) Uani 1 1 d . . . . .
C13 C 0.6430(10) 0.49111(18) 0.8983(2) 0.0598(9) Uani 1 1 d . . . . .
H13 H 0.730751 0.496308 0.953536 0.072 Uiso 1 1 calc R . . . .
C14 C 0.4696(11) 0.54628(18) 0.8606(2) 0.0646(10) Uani 1 1 d . . . . .
H14 H 0.435165 0.589800 0.889184 0.078 Uiso 1 1 calc R . . . .
C15 C 0.3438(10) 0.53807(18) 0.7798(2) 0.0613(9) Uani 1 1 d . . . . .
H15 H 0.222644 0.576397 0.753104 0.074 Uiso 1 1 calc R . . . .
C16 C 0.3914(10) 0.47581(17) 0.7381(2) 0.0577(9) Uani 1 1 d . . . . .
H16 H 0.300384 0.471665 0.683006 0.069 Uiso 1 1 calc R . . . .
C21 C 0.5362(10) 0.34334(17) 0.64861(19) 0.0556(9) Uani 1 1 d D . . . .
C22 C 0.3750(10) 0.28354(17) 0.6170(2) 0.0579(9) Uani 1 1 d . . . . .
C23 C 0.3665(10) 0.2826(2) 0.5296(2) 0.0627(9) Uani 1 1 d . . . . .
H23 H 0.269310 0.244789 0.497048 0.075 Uiso 1 1 calc R . . . .
C24 C 0.5109(11) 0.3410(2) 0.4980(2) 0.0692(10) Uani 1 1 d D . . . .
C2 C 0.2279(10) 0.23227(18) 0.6702(2) 0.0614(9) Uani 1 1 d . . . . .
C3 C 0.5454(15) 0.3597(3) 0.4078(3) 0.0978(15) Uani 1 1 d . . . . .
H3A H 0.447454 0.407222 0.396798 0.147 Uiso 1 1 calc GR . . . .
H3B H 0.420195 0.324263 0.373336 0.147 Uiso 1 1 calc GR . . . .
H3C H 0.790723 0.359493 0.395072 0.147 Uiso 1 1 calc GR . . . .
H1 H 0.708(10) 0.3233(17) 0.762(2) 0.079(13) Uiso 1 1 d D . . . .
O1B O 0.601(6) 0.3708(8) 0.5745(3) 0.0627(5) Uani 0.147(6) 1 d D . P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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
C24 S1 C21 90.84(19) . . ?
C11 N1 C21 126.6(3) . . ?
C11 N1 H1 111(3) . . ?
C21 N1 H1 122(3) . . ?
O21 N2 C12 120.1(3) . . ?
O22 N2 O21 121.1(3) . . ?
O22 N2 C12 118.9(3) . . ?
N1 C11 C12 122.3(3) . . ?
N1 C11 C16 121.5(3) . . ?
C16 C11 C12 116.2(3) . . ?
C11 C12 N2 122.1(3) . . ?
C13 C12 N2 116.7(3) . . ?
C13 C12 C11 121.1(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C11 C16 H16 119.1 . . ?
C15 C16 C11 121.9(3) . . ?
C15 C16 H16 119.1 . . ?
N1 C21 S1 122.7(3) . . ?
C22 C21 S1 111.1(2) . . ?
C22 C21 N1 125.8(3) . . ?
O1B C21 N1 139.2(5) . . ?
O1B C21 C22 94.4(5) . . ?
C21 C22 C23 112.0(3) . . ?
C21 C22 C2 120.6(3) . . ?
C23 C22 C2 127.4(3) . . ?
C22 C23 H23 123.7 . . ?
C24 C23 C22 112.5(3) . . ?
C24 C23 H23 123.7 . . ?
C23 C24 S1 113.5(3) . . ?
C23 C24 C3 127.9(4) . . ?
C23 C24 O1B 94.3(5) . . ?
C3 C24 S1 118.6(4) . . ?
O1B C24 C3 137.8(5) . . ?
N3 C2 C22 176.4(4) . . ?
C24 C3 H3A 109.5 . . ?
C24 C3 H3B 109.5 . . ?
C24 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C21 O1B C24 126.8(7) . . ?
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
S1 C21 1.739(3) . ?
S1 C24 1.696(4) . ?
O21 N2 1.238(4) . ?
O22 N2 1.232(4) . ?
N1 C11 1.379(4) . ?
N1 C21 1.386(4) . ?
N1 H1 0.842(19) . ?
N2 C12 1.444(4) . ?
N3 C2 1.147(5) . ?
C11 C12 1.412(4) . ?
C11 C16 1.400(5) . ?
C12 C13 1.394(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.360(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.365(5) . ?
C16 H16 0.9500 . ?
C21 C22 1.369(5) . ?
C21 O1B 1.344(5) . ?
C22 C23 1.420(5) . ?
C22 C2 1.428(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.340(6) . ?
C24 C3 1.520(6) . ?
C24 O1B 1.392(5) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
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 0.842(19) 1.91(3) 2.611(4) 140(4) . 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
S1 C21 C22 C23 1.1(4) . . . . ?
S1 C21 C22 C2 -176.6(3) . . . . ?
O21 N2 C12 C11 -3.8(5) . . . . ?
O21 N2 C12 C13 177.1(3) . . . . ?
O22 N2 C12 C11 176.2(3) . . . . ?
O22 N2 C12 C13 -2.9(5) . . . . ?
N1 C11 C12 N2 -0.6(5) . . . . ?
N1 C11 C12 C13 178.5(3) . . . . ?
N1 C11 C16 C15 -178.6(3) . . . . ?
N1 C21 C22 C23 -171.5(3) . . . . ?
N1 C21 C22 C2 10.8(6) . . . . ?
N1 C21 O1B C24 170.6(9) . . . . ?
N2 C12 C13 C14 -180.0(3) . . . . ?
C11 N1 C21 S1 53.7(5) . . . . ?
C11 N1 C21 C22 -134.4(4) . . . . ?
C11 N1 C21 O1B 57.8(17) . . . . ?
C11 C12 C13 C14 0.9(6) . . . . ?
C12 C11 C16 C15 1.2(5) . . . . ?
C12 C13 C14 C15 -0.2(6) . . . . ?
C13 C14 C15 C16 0.0(6) . . . . ?
C14 C15 C16 C11 -0.6(6) . . . . ?
C16 C11 C12 N2 179.6(3) . . . . ?
C16 C11 C12 C13 -1.3(5) . . . . ?
C21 S1 C24 C23 -0.3(3) . . . . ?
C21 S1 C24 C3 179.7(4) . . . . ?
C21 N1 C11 C12 -175.0(3) . . . . ?
C21 N1 C11 C16 4.8(6) . . . . ?
C21 C22 C23 C24 -1.4(5) . . . . ?
C22 C21 O1B C24 0(2) . . . . ?
C22 C23 C24 S1 1.0(5) . . . . ?
C22 C23 C24 C3 -179.0(4) . . . . ?
C22 C23 C24 O1B 1.4(11) . . . . ?
C23 C24 O1B C21 -1(2) . . . . ?
C24 S1 C21 N1 172.4(3) . . . . ?
C24 S1 C21 C22 -0.5(3) . . . . ?
C2 C22 C23 C24 176.1(4) . . . . ?
C3 C24 O1B C21 179.2(11) . . . . ?
O1B C21 C22 C23 0.5(11) . . . . ?
O1B C21 C22 C2 -177.2(11) . . . . ?
