# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_wv580
_database_code_depnum_ccdc_archive 'CCDC 2044215'
loop_
_audit_author_name
_audit_author_address
'Peter Mayer'
;LMU Muenchen
Germany
;



_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;

_chemical_name_common            RM436
_chemical_compound_source        ?
_chemical_absolute_configuration ?

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.100 #?# in millimeters
_exptl_crystal_size_mid          0.030 #?# in millimeters
_exptl_crystal_size_min          0.020 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
;
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      108.(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (TXS)'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    ?
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_measurement_details      ?
_diffrn_detector_area_resol_mean 7.3910

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   14.2681(7)
_cell_length_b                   3.9182(2)
_cell_length_c                   17.1782(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.954(2)
_cell_angle_gamma                90
_cell_volume                     902.70(8)
_cell_measurement_temperature    108.(2) #?# in K
_cell_measurement_reflns_used    3311
_cell_measurement_theta_min      3.0378
_cell_measurement_theta_max      26.7428
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  1.00
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_diffrn_reflns_number            8211 #xl
_diffrn_reflns_av_R_equivalents  0.0394 #xl
_diffrn_reflns_av_unetI/netI     0.0335 #xl
_diffrn_reflns_limit_h_min       -17 #xl
_diffrn_reflns_limit_h_max       18 #xl
_diffrn_reflns_limit_k_min       -4 #xl
_diffrn_reflns_limit_k_max       4 #xl
_diffrn_reflns_limit_l_min       -21 #xl
_diffrn_reflns_limit_l_max       17 #xl
_diffrn_reflns_theta_min         3.219 #xl
_diffrn_reflns_theta_max         26.732 #xl
_diffrn_measured_fraction_theta_max 0.998 #xl
_diffrn_reflns_theta_full        25.242 #xl
_diffrn_measured_fraction_theta_full 0.998 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.998 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.998 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.998 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.998 #xl

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14

_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.
;

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_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'

_reflns_number_total             1897 #xl
_reflns_number_gt                1521 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.000 #xl
_reflns_Friedel_fraction_max     . #xl
_reflns_Friedel_fraction_full    . #xl
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+0.5869P] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr #?#
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details ? #xl
_refine_ls_abs_structure_Flack   ? #xl
_refine_ls_number_reflns         1897 #xl
_refine_ls_number_parameters     136 #xl
_refine_ls_number_restraints     0 #xl
_refine_ls_R_factor_all          0.0598 #xl
_refine_ls_R_factor_gt           0.0460 #xl
_refine_ls_wR_factor_ref         0.1119 #xl
_refine_ls_wR_factor_gt          0.1064 #xl
_refine_ls_goodness_of_fit_ref   1.089 #xl
_refine_ls_restrained_S_all      1.089 #xl
_refine_ls_shift/su_max          0.000 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.243 #xl
_refine_diff_density_min         -0.243 #xl
_refine_diff_density_rms         0.047 #xl

_refine_special_details          
;
;

_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'

_computing_publication_material  ?

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 0.31101(9) 0.0642(4) 0.05504(7) 0.0248(3) Uani 1 1 d . . . . .
N1 N 0.26954(10) 0.1378(4) 0.30372(8) 0.0173(3) Uani 1 1 d . . . . .
N2 N 0.07342(12) 0.5432(5) 0.34323(10) 0.0304(4) Uani 1 1 d . . . . .
C1 C 0.30786(13) 0.0533(5) 0.38599(10) 0.0211(4) Uani 1 1 d . . . . .
H1 H 0.274181 0.118697 0.422753 0.025 Uiso 1 1 calc R U . . .
C2 C 0.39413(13) -0.1242(5) 0.41418(11) 0.0235(4) Uani 1 1 d . . . . .
H2 H 0.420674 -0.185373 0.471045 0.028 Uiso 1 1 calc R U . . .
C3 C 0.44548(13) -0.2202(5) 0.36016(11) 0.0223(4) Uani 1 1 d . . . . .
H3 H 0.506463 -0.342686 0.380718 0.027 Uiso 1 1 calc R U . . .
C4 C 0.40656(12) -0.1350(5) 0.27801(10) 0.0191(4) Uani 1 1 d . . . . .
H4 H 0.440437 -0.199465 0.241324 0.023 Uiso 1 1 calc R U . . .
C5 C 0.31684(12) 0.0471(4) 0.24803(10) 0.0165(4) Uani 1 1 d . . . . .
C6 C 0.25582(12) 0.1710(5) 0.17067(10) 0.0170(4) Uani 1 1 d . . . . .
C7 C 0.25109(13) 0.1795(5) 0.08501(10) 0.0181(4) Uani 1 1 d . . . . .
C8 C 0.15358(13) 0.3585(5) 0.03661(10) 0.0205(4) Uani 1 1 d . . . . .
H8A H 0.110596 0.204472 -0.006574 0.025 Uiso 1 1 calc R U . . .
H8B H 0.167262 0.565719 0.009284 0.025 Uiso 1 1 calc R U . . .
C9 C 0.10074(12) 0.4565(5) 0.09892(10) 0.0193(4) Uani 1 1 d . . . . .
H9A H 0.091010 0.706320 0.100100 0.023 Uiso 1 1 calc R U . . .
H9B H 0.035338 0.341215 0.085192 0.023 Uiso 1 1 calc R U . . .
C10 C 0.17288(12) 0.3303(4) 0.17978(10) 0.0170(4) Uani 1 1 d . . . . .
C11 C 0.18063(12) 0.3136(5) 0.26170(10) 0.0186(4) Uani 1 1 d . . . . .
C12 C 0.11997(13) 0.4397(5) 0.30575(10) 0.0219(4) Uani 1 1 d . . . . .


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 C7 1.225(2) . ?
N1 C1 1.371(2) . ?
N1 C5 1.392(2) . ?
N1 C11 1.407(2) . ?
N2 C12 1.145(2) . ?
C1 C2 1.351(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.415(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.370(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(2) . ?
C6 C10 1.393(2) . ?
C6 C7 1.450(2) . ?
C7 C8 1.526(2) . ?
C8 C9 1.553(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.502(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.375(2) . ?
C11 C12 1.419(2) . ?

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 C5 122.04(15) . . ?
C1 N1 C11 128.31(14) . . ?
C5 N1 C11 109.64(13) . . ?
C2 C1 N1 119.20(16) . . ?
C2 C1 H1 120.4 . . ?
N1 C1 H1 120.4 . . ?
C1 C2 C3 120.91(16) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 119.48(17) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.07(16) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 118.29(15) . . ?
N1 C5 C6 105.83(14) . . ?
C4 C5 C6 135.88(15) . . ?
C10 C6 C5 108.96(14) . . ?
C10 C6 C7 110.88(15) . . ?
C5 C6 C7 140.15(16) . . ?
O1 C7 C6 128.35(17) . . ?
O1 C7 C8 125.28(15) . . ?
C6 C7 C8 106.35(14) . . ?
C7 C8 C9 107.74(13) . . ?
C7 C8 H8A 110.2 . . ?
C9 C8 H8A 110.2 . . ?
C7 C8 H8B 110.2 . . ?
C9 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C10 C9 C8 102.43(13) . . ?
C10 C9 H9A 111.3 . . ?
C8 C9 H9A 111.3 . . ?
C10 C9 H9B 111.3 . . ?
C8 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C11 C10 C6 108.59(15) . . ?
C11 C10 C9 138.79(16) . . ?
C6 C10 C9 112.57(14) . . ?
C10 C11 N1 106.97(14) . . ?
C10 C11 C12 132.74(16) . . ?
N1 C11 C12 120.27(15) . . ?
N2 C12 C11 178.04(19) . . ?

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
C5 N1 C1 C2 -0.1(3) . . . . ?
C11 N1 C1 C2 178.57(17) . . . . ?
N1 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C1 N1 C5 C4 -0.3(2) . . . . ?
C11 N1 C5 C4 -179.18(15) . . . . ?
C1 N1 C5 C6 179.13(15) . . . . ?
C11 N1 C5 C6 0.22(19) . . . . ?
C3 C4 C5 N1 0.2(3) . . . . ?
C3 C4 C5 C6 -179.0(2) . . . . ?
N1 C5 C6 C10 -0.56(19) . . . . ?
C4 C5 C6 C10 178.69(19) . . . . ?
N1 C5 C6 C7 -179.0(2) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
C10 C6 C7 O1 -179.99(18) . . . . ?
C5 C6 C7 O1 -1.5(4) . . . . ?
C10 C6 C7 C8 -1.1(2) . . . . ?
C5 C6 C7 C8 177.4(2) . . . . ?
O1 C7 C8 C9 179.07(17) . . . . ?
C6 C7 C8 C9 0.11(19) . . . . ?
C7 C8 C9 C10 0.78(19) . . . . ?
C5 C6 C10 C11 0.7(2) . . . . ?
C7 C6 C10 C11 179.64(15) . . . . ?
C5 C6 C10 C9 -177.26(15) . . . . ?
C7 C6 C10 C9 1.7(2) . . . . ?
C8 C9 C10 C11 -178.6(2) . . . . ?
C8 C9 C10 C6 -1.5(2) . . . . ?
C6 C10 C11 N1 -0.5(2) . . . . ?
C9 C10 C11 N1 176.6(2) . . . . ?
C6 C10 C11 C12 178.0(2) . . . . ?
C9 C10 C11 C12 -4.8(4) . . . . ?
C1 N1 C11 C10 -178.62(17) . . . . ?
C5 N1 C11 C10 0.2(2) . . . . ?
C1 N1 C11 C12 2.6(3) . . . . ?
C5 N1 C11 C12 -178.60(17) . . . . ?

_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

_audit_block_code                C12H8N2O_wv580_mayr
_audit_creation_method           'APEX3 v2017.3-0'
_shelxl_version_number           ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 N2 O'
_chemical_formula_sum            'C12 H8 N2 O'
_chemical_formula_weight         196.20 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            4 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             408 #?# check!

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_wv581
_database_code_depnum_ccdc_archive 'CCDC 2044217'
loop_
_audit_author_name
_audit_author_address
'Peter Mayer'
;LMU Muenchen
Germany
;

_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;

_chemical_name_common            RM447
_chemical_compound_source        ?
_chemical_absolute_configuration ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.080 #?# in millimeters
_exptl_crystal_size_mid          0.060 #?# in millimeters
_exptl_crystal_size_min          0.050 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
;
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      108.(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (TXS)'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    ?
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_measurement_details      ?
_diffrn_detector_area_resol_mean 7.3910

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   10.6358(4)
_cell_length_b                   9.5636(4)
_cell_length_c                   10.4269(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.187(2)
_cell_angle_gamma                90
_cell_volume                     1043.87(7)
_cell_measurement_temperature    108.(2) #?# in K
_cell_measurement_reflns_used    4879
_cell_measurement_theta_min      2.8849
_cell_measurement_theta_max      27.0815
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.99
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_diffrn_reflns_number            10661 #xl
_diffrn_reflns_av_R_equivalents  0.0344 #xl
_diffrn_reflns_av_unetI/netI     0.0279 #xl
_diffrn_reflns_limit_h_min       -13 #xl
_diffrn_reflns_limit_h_max       13 #xl
_diffrn_reflns_limit_k_min       -12 #xl
_diffrn_reflns_limit_k_max       12 #xl
_diffrn_reflns_limit_l_min       -13 #xl
_diffrn_reflns_limit_l_max       11 #xl
_diffrn_reflns_theta_min         2.885 #xl
_diffrn_reflns_theta_max         27.081 #xl
_diffrn_measured_fraction_theta_max 0.998 #xl
_diffrn_reflns_theta_full        25.242 #xl
_diffrn_measured_fraction_theta_full 0.997 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.998 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.997 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.998 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.997 #xl

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14

_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.
;

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_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'

_reflns_number_total             2298 #xl
_reflns_number_gt                1971 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.000 #xl
_reflns_Friedel_fraction_max     . #xl
_reflns_Friedel_fraction_full    . #xl
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+0.5066P] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr #?#
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details ? #xl
_refine_ls_abs_structure_Flack   ? #xl
_refine_ls_number_reflns         2298 #xl
_refine_ls_number_parameters     145 #xl
_refine_ls_number_restraints     0 #xl
_refine_ls_R_factor_all          0.0481 #xl
_refine_ls_R_factor_gt           0.0401 #xl
_refine_ls_wR_factor_ref         0.1025 #xl
_refine_ls_wR_factor_gt          0.0976 #xl
_refine_ls_goodness_of_fit_ref   1.036 #xl
_refine_ls_restrained_S_all      1.036 #xl
_refine_ls_shift/su_max          0.000 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.243 #xl
_refine_diff_density_min         -0.205 #xl
_refine_diff_density_rms         0.043 #xl

_refine_special_details          
;
;

_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'

_computing_publication_material  ?

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 0.41843(9) 0.68753(11) 0.87282(9) 0.0253(2) Uani 1 1 d . . . . .
O2 O 0.44558(10) 0.85591(11) 0.73767(10) 0.0294(3) Uani 1 1 d . . . . .
N1 N 0.06818(12) 0.29812(13) -0.00227(12) 0.0280(3) Uani 1 1 d . . . . .
C1 C 0.38988(12) 0.74939(15) 0.75523(13) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.29018(12) 0.68827(14) 0.65376(13) 0.0187(3) Uani 1 1 d . . . . .
H2 H 0.250464 0.753760 0.583352 0.022 Uiso 1 1 calc R U . . .
C3 C 0.30299(12) 0.53560(14) 0.61191(12) 0.0189(3) Uani 1 1 d . . . . .
H3 H 0.378278 0.483473 0.660108 0.023 Uiso 1 1 calc R U . . .
C4 C 0.20340(12) 0.57738(14) 0.69118(13) 0.0191(3) Uani 1 1 d . . . . .
H4 H 0.113077 0.579213 0.643697 0.023 Uiso 1 1 calc R U . . .
C5 C 0.22181(12) 0.54299(15) 0.83420(13) 0.0215(3) Uani 1 1 d . . . . .
H5A H 0.191156 0.446738 0.845200 0.026 Uiso 1 1 calc R U . . .
H5B H 0.170008 0.607803 0.877546 0.026 Uiso 1 1 calc R U . . .
C6 C 0.36070(13) 0.55429(15) 0.89881(13) 0.0228(3) Uani 1 1 d . . . . .
H6A H 0.366973 0.542953 0.994103 0.027 Uiso 1 1 calc R U . . .
H6B H 0.409431 0.477235 0.867266 0.027 Uiso 1 1 calc R U . . .
C7 C 0.26266(12) 0.49701(13) 0.47256(12) 0.0181(3) Uani 1 1 d . . . . .
C8 C 0.15864(12) 0.56174(14) 0.39384(13) 0.0201(3) Uani 1 1 d . . . . .
H8 H 0.117327 0.638107 0.427311 0.024 Uiso 1 1 calc R U . . .
C9 C 0.11523(12) 0.51599(14) 0.26802(13) 0.0206(3) Uani 1 1 d . . . . .
H9 H 0.045162 0.561274 0.215032 0.025 Uiso 1 1 calc R U . . .
C10 C 0.17507(13) 0.40278(14) 0.21940(13) 0.0198(3) Uani 1 1 d . . . . .
C11 C 0.28277(13) 0.34186(14) 0.29440(13) 0.0210(3) Uani 1 1 d . . . . .
H11 H 0.326004 0.267846 0.259664 0.025 Uiso 1 1 calc R U . . .
C12 C 0.32641(12) 0.38980(14) 0.41978(13) 0.0203(3) Uani 1 1 d . . . . .
H12 H 0.400505 0.349218 0.470325 0.024 Uiso 1 1 calc R U . . .
C13 C 0.11854(13) 0.34493(14) 0.09459(13) 0.0216(3) Uani 1 1 d . . . . .


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 1.3468(17) . ?
O1 C6 1.4606(17) . ?
O2 C1 1.2086(17) . ?
N1 C13 1.1472(18) . ?
C1 C2 1.4794(18) . ?
C2 C4 1.5021(18) . ?
C2 C3 1.5368(18) . ?
C2 H2 1.0000 . ?
C3 C7 1.4869(18) . ?
C3 C4 1.5081(18) . ?
C3 H3 1.0000 . ?
C4 C5 1.5056(18) . ?
C4 H4 1.0000 . ?
C5 C6 1.5151(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C12 1.3950(18) . ?
C7 C8 1.4000(18) . ?
C8 C9 1.3825(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.3958(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.3951(19) . ?
C10 C13 1.4438(18) . ?
C11 C12 1.3857(19) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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 O1 C6 121.17(10) . . ?
O2 C1 O1 118.06(12) . . ?
O2 C1 C2 122.23(13) . . ?
O1 C1 C2 119.68(12) . . ?
C1 C2 C4 119.26(11) . . ?
C1 C2 C3 119.35(11) . . ?
C4 C2 C3 59.50(8) . . ?
C1 C2 H2 115.7 . . ?
C4 C2 H2 115.7 . . ?
C3 C2 H2 115.7 . . ?
C7 C3 C4 119.48(11) . . ?
C7 C3 C2 119.24(11) . . ?
C4 C3 C2 59.11(8) . . ?
C7 C3 H3 115.7 . . ?
C4 C3 H3 115.7 . . ?
C2 C3 H3 115.7 . . ?
C2 C4 C5 115.67(11) . . ?
C2 C4 C3 61.40(8) . . ?
C5 C4 C3 120.27(11) . . ?
C2 C4 H4 116.1 . . ?
C5 C4 H4 116.1 . . ?
C3 C4 H4 116.1 . . ?
C4 C5 C6 111.75(11) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
O1 C6 C5 112.86(11) . . ?
O1 C6 H6A 109.0 . . ?
C5 C6 H6A 109.0 . . ?
O1 C6 H6B 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C12 C7 C8 118.85(12) . . ?
C12 C7 C3 119.45(12) . . ?
C8 C7 C3 121.65(12) . . ?
C9 C8 C7 120.87(12) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.53(12) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.15(12) . . ?
C11 C10 C13 120.99(12) . . ?
C9 C10 C13 118.73(12) . . ?
C12 C11 C10 119.70(12) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C7 120.69(12) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
N1 C13 C10 176.65(14) . . ?

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
C6 O1 C1 O2 -176.32(12) . . . . ?
C6 O1 C1 C2 5.35(18) . . . . ?
O2 C1 C2 C4 -165.34(12) . . . . ?
O1 C1 C2 C4 12.92(18) . . . . ?
O2 C1 C2 C3 125.29(14) . . . . ?
O1 C1 C2 C3 -56.45(17) . . . . ?
C1 C2 C3 C7 -142.56(12) . . . . ?
C4 C2 C3 C7 108.80(13) . . . . ?
C1 C2 C3 C4 108.64(13) . . . . ?
C1 C2 C4 C5 3.23(17) . . . . ?
C3 C2 C4 C5 112.01(12) . . . . ?
C1 C2 C4 C3 -108.78(13) . . . . ?
C7 C3 C4 C2 -108.40(13) . . . . ?
C7 C3 C4 C5 146.94(12) . . . . ?
C2 C3 C4 C5 -104.66(13) . . . . ?
C2 C4 C5 C6 -34.37(16) . . . . ?
C3 C4 C5 C6 36.09(17) . . . . ?
C1 O1 C6 C5 -38.18(16) . . . . ?
C4 C5 C6 O1 51.48(15) . . . . ?
C4 C3 C7 C12 -143.13(13) . . . . ?
C2 C3 C7 C12 147.93(12) . . . . ?
C4 C3 C7 C8 34.21(18) . . . . ?
C2 C3 C7 C8 -34.73(18) . . . . ?
C12 C7 C8 C9 3.3(2) . . . . ?
C3 C7 C8 C9 -174.07(12) . . . . ?
C7 C8 C9 C10 0.7(2) . . . . ?
C8 C9 C10 C11 -3.94(19) . . . . ?
C8 C9 C10 C13 172.04(12) . . . . ?
C9 C10 C11 C12 3.1(2) . . . . ?
C13 C10 C11 C12 -172.76(12) . . . . ?
C10 C11 C12 C7 0.9(2) . . . . ?
C8 C7 C12 C11 -4.1(2) . . . . ?
C3 C7 C12 C11 173.31(12) . . . . ?

_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

_audit_block_code                C13H11NO2_wv581_mayr
_audit_creation_method           'APEX3 v2017.3-0'
_shelxl_version_number           ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N O2'
_chemical_formula_sum            'C13 H11 N O2'
_chemical_formula_weight         213.23 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            4 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             448 #?# check!

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yv471
_database_code_depnum_ccdc_archive 'CCDC 2044216'
loop_
_audit_author_name
_audit_author_address
'Peter Mayer'
;LMU Muenchen
Germany
;

_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;

_chemical_name_common            RNH389f2
_chemical_compound_source        ?
_chemical_absolute_configuration ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.120 #?# in millimeters
_exptl_crystal_size_mid          0.100 #?# in millimeters
_exptl_crystal_size_min          0.090 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
;
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      102.(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (TXS)'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    ?
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_measurement_details      ?
_diffrn_detector_area_resol_mean 7.3910

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   10.8844(9)
_cell_length_b                   9.9707(7)
_cell_length_c                   9.1680(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.835(3)
_cell_angle_gamma                90
_cell_volume                     994.45(13)
_cell_measurement_temperature    102.(2) #?# in K
_cell_measurement_reflns_used    7361
_cell_measurement_theta_min      2.7711
_cell_measurement_theta_max      28.2542
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.99
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_diffrn_reflns_number            17273 #xl
_diffrn_reflns_av_R_equivalents  0.0482 #xl
_diffrn_reflns_av_unetI/netI     0.0321 #xl
_diffrn_reflns_limit_h_min       -14 #xl
_diffrn_reflns_limit_h_max       14 #xl
_diffrn_reflns_limit_k_min       -13 #xl
_diffrn_reflns_limit_k_max       13 #xl
_diffrn_reflns_limit_l_min       -12 #xl
_diffrn_reflns_limit_l_max       12 #xl
_diffrn_reflns_theta_min         3.019 #xl
_diffrn_reflns_theta_max         28.282 #xl
_diffrn_measured_fraction_theta_max 0.998 #xl
_diffrn_reflns_theta_full        25.242 #xl
_diffrn_measured_fraction_theta_full 0.997 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.998 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.997 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.998 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.997 #xl

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14

_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.
;

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_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'

_reflns_number_total             2461 #xl
_reflns_number_gt                2059 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.000 #xl
_reflns_Friedel_fraction_max     . #xl
_reflns_Friedel_fraction_full    . #xl
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0483P)²+0.4815P] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr #?#
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details ? #xl
_refine_ls_abs_structure_Flack   ? #xl
_refine_ls_number_reflns         2461 #xl
_refine_ls_number_parameters     141 #xl
_refine_ls_number_restraints     0 #xl
_refine_ls_R_factor_all          0.0529 #xl
_refine_ls_R_factor_gt           0.0415 #xl
_refine_ls_wR_factor_ref         0.1163 #xl
_refine_ls_wR_factor_gt          0.1046 #xl
_refine_ls_goodness_of_fit_ref   1.043 #xl
_refine_ls_restrained_S_all      1.043 #xl
_refine_ls_shift/su_max          0.000 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.241 #xl
_refine_diff_density_min         -0.214 #xl
_refine_diff_density_rms         0.046 #xl

_refine_special_details          
;
The O-atom is disordered. The sof ratio of the two parts refined to 0.966/0.034.
;

_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'

_computing_publication_material  ?

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
C1 C 0.17780(11) 0.53214(12) 0.61837(13) 0.0205(3) Uani 1 1 d . . . . .
H1 H 0.095694 0.489786 0.632110 0.025 Uiso 1 1 calc R U . A 1
O1 O 0.03318(9) 0.82127(10) 0.75894(11) 0.0289(3) Uani 0.966(3) 1 d . . P B 1
C2 C 0.25328(12) 0.55600(13) 0.75574(14) 0.0237(3) Uani 0.966(3) 1 d . . P B 1
H2 H 0.344638 0.546312 0.753440 0.028 Uiso 0.966(3) 1 calc R U P B 1
C3 C 0.19274(11) 0.67459(12) 0.68012(14) 0.0219(3) Uani 0.966(3) 1 d . . P B 1
H3 H 0.243381 0.742536 0.628879 0.026 Uiso 0.966(3) 1 calc R U P B 1
C4 C 0.09006(11) 0.71763(12) 0.77171(13) 0.0215(3) Uani 0.966(3) 1 d . . P B 1
C5 C 0.06892(12) 0.61088(13) 0.88615(14) 0.0246(3) Uani 0.966(3) 1 d . . P B 1
H5A H -0.000356 0.551829 0.855603 0.029 Uiso 0.966(3) 1 calc R U P B 1
H5AB H 0.050222 0.652535 0.980922 0.029 Uiso 0.966(3) 1 calc R U P B 1
C6 C 0.18925(13) 0.53098(14) 0.89841(14) 0.0287(3) Uani 0.966(3) 1 d . . P B 1
H6A H 0.240802 0.562589 0.982447 0.034 Uiso 0.966(3) 1 calc R U P B 1
H6AB H 0.172303 0.434197 0.911103 0.034 Uiso 0.966(3) 1 calc R U P B 1
O1B O 0.191(3) 0.451(4) 0.980(4) 0.044(10) Uiso 0.034(3) 1 d . . P B 2
C2B C 0.25328(12) 0.55600(13) 0.75574(14) 0.0237(3) Uani 0.034(3) 1 d . . P B 2
H2B H 0.344638 0.546312 0.753440 0.028 Uiso 0.034(3) 1 calc R U P B 2
C3B C 0.19274(11) 0.67459(12) 0.68012(14) 0.0219(3) Uani 0.034(3) 1 d . . P B 2
H3B H 0.243381 0.742536 0.628879 0.026 Uiso 0.034(3) 1 calc R U P B 2
C4B C 0.09006(11) 0.71763(12) 0.77171(13) 0.0215(3) Uani 0.034(3) 1 d . . P B 2
H4A H 0.014526 0.730111 0.710159 0.026 Uiso 0.034(3) 1 calc R U P B 2
H4AB H 0.110498 0.804112 0.819670 0.026 Uiso 0.034(3) 1 calc R U P B 2
C5B C 0.06892(12) 0.61088(13) 0.88615(14) 0.0246(3) Uani 0.034(3) 1 d . . P B 2
H5C H -0.000356 0.551829 0.855603 0.029 Uiso 0.034(3) 1 calc R U P B 2
H5D H 0.050222 0.652535 0.980922 0.029 Uiso 0.034(3) 1 calc R U P B 2
C6B C 0.18925(13) 0.53098(14) 0.89841(14) 0.0287(3) Uani 0.034(3) 1 d . . P B 2
C7 C 0.23924(11) 0.49492(12) 0.48162(13) 0.0197(3) Uani 1 1 d . . . . .
C8 C 0.19527(12) 0.38377(13) 0.40315(14) 0.0229(3) Uani 1 1 d . . . . .
H8 H 0.125212 0.337079 0.435817 0.027 Uiso 1 1 calc R U . . .
C9 C 0.25211(12) 0.34051(13) 0.27848(14) 0.0240(3) Uani 1 1 d . . . . .
H9 H 0.221921 0.264079 0.226885 0.029 Uiso 1 1 calc R U . . .
C10 C 0.35405(11) 0.41011(13) 0.22934(13) 0.0224(3) Uani 1 1 d . . . . .
C11 C 0.39732(12) 0.52298(13) 0.30443(14) 0.0248(3) Uani 1 1 d . . . . .
H11 H 0.465399 0.571720 0.269568 0.030 Uiso 1 1 calc R U . . .
C12 C 0.34065(11) 0.56392(13) 0.43025(14) 0.0241(3) Uani 1 1 d . . . . .
H12 H 0.371289 0.639968 0.482156 0.029 Uiso 1 1 calc R U . . .
C13 C 0.41650(12) 0.36449(13) 0.10175(14) 0.0251(3) Uani 1 1 d . . . . .
N1 N 0.46719(12) 0.32889(13) 0.00087(13) 0.0330(3) Uani 1 1 d . . . . .


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
C1 C7 1.4868(16) . ?
C1 C2 1.5004(17) . ?
C1 C2B 1.5004(17) . ?
C1 C3 1.5357(17) . ?
C1 C3B 1.5357(17) . ?
C1 H1 1.0000 . ?
O1 C4 1.2084(15) . ?
C2 C3 1.5112(17) . ?
C2 C6 1.5222(18) . ?
C2 H2 1.0000 . ?
C3 C4 1.4827(17) . ?
C3 H3 1.0000 . ?
C4 C5 1.5172(17) . ?
C5 C6 1.5341(19) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
O1B C6B 1.09(4) . ?
C2B C3B 1.5112(17) . ?
C2B C6B 1.5222(18) . ?
C2B H2B 1.0000 . ?
C3B C4B 1.4827(17) . ?
C3B H3B 1.0000 . ?
C4B C5B 1.5172(17) . ?
C4B H4A 0.9900 . ?
C4B H4AB 0.9900 . ?
C5B C6B 1.5341(19) . ?
C5B H5C 0.9900 . ?
C5B H5D 0.9900 . ?
C7 C12 1.3953(17) . ?
C7 C8 1.3974(17) . ?
C8 C9 1.3858(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.3956(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.3934(18) . ?
C10 C13 1.4450(17) . ?
C11 C12 1.3868(17) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 N1 1.1482(18) . ?

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
C7 C1 C2 119.89(10) . . ?
C7 C1 C2B 119.89(10) . . ?
C7 C1 C3 119.77(10) . . ?
C2 C1 C3 59.69(8) . . ?
C7 C1 C3B 119.77(10) . . ?
C2B C1 C3B 59.69(8) . . ?
C7 C1 H1 115.4 . . ?
C2 C1 H1 115.4 . . ?
C3 C1 H1 115.4 . . ?
C1 C2 C3 61.32(8) . . ?
C1 C2 C6 116.22(11) . . ?
C3 C2 C6 108.52(10) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C6 C2 H2 119.0 . . ?
C4 C3 C2 106.99(10) . . ?
C4 C3 C1 113.80(10) . . ?
C2 C3 C1 59.00(8) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C1 C3 H3 120.5 . . ?
O1 C4 C3 125.85(12) . . ?
O1 C4 C5 125.34(12) . . ?
C3 C4 C5 108.81(10) . . ?
C4 C5 C6 105.48(11) . . ?
C4 C5 H5A 110.6 . . ?
C6 C5 H5A 110.6 . . ?
C4 C5 H5AB 110.6 . . ?
C6 C5 H5AB 110.6 . . ?
H5A C5 H5AB 108.8 . . ?
C2 C6 C5 105.38(10) . . ?
C2 C6 H6A 110.7 . . ?
C5 C6 H6A 110.7 . . ?
C2 C6 H6AB 110.7 . . ?
C5 C6 H6AB 110.7 . . ?
H6A C6 H6AB 108.8 . . ?
C1 C2B C3B 61.32(8) . . ?
C1 C2B C6B 116.22(11) . . ?
C3B C2B C6B 108.52(10) . . ?
C1 C2B H2B 119.0 . . ?
C3B C2B H2B 119.0 . . ?
C6B C2B H2B 119.0 . . ?
C4B C3B C2B 106.99(10) . . ?
C4B C3B C1 113.80(10) . . ?
C2B C3B C1 59.00(8) . . ?
C4B C3B H3B 120.5 . . ?
C2B C3B H3B 120.5 . . ?
C1 C3B H3B 120.5 . . ?
C3B C4B C5B 108.81(10) . . ?
C3B C4B H4A 109.9 . . ?
C5B C4B H4A 109.9 . . ?
C3B C4B H4AB 109.9 . . ?
C5B C4B H4AB 109.9 . . ?
H4A C4B H4AB 108.3 . . ?
C4B C5B C6B 105.48(11) . . ?
C4B C5B H5C 110.6 . . ?
C6B C5B H5C 110.6 . . ?
C4B C5B H5D 110.6 . . ?
C6B C5B H5D 110.6 . . ?
H5C C5B H5D 108.8 . . ?
O1B C6B C2B 135.4(19) . . ?
O1B C6B C5B 114.9(18) . . ?
C2B C6B C5B 105.38(10) . . ?
C12 C7 C8 118.61(11) . . ?
C12 C7 C1 122.93(11) . . ?
C8 C7 C1 118.44(11) . . ?
C9 C8 C7 121.12(11) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 119.47(12) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.12(11) . . ?
C11 C10 C13 119.59(12) . . ?
C9 C10 C13 120.28(12) . . ?
C12 C11 C10 119.76(12) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C7 120.89(12) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
N1 C13 C10 179.31(15) . . ?

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
C7 C1 C2 C3 109.11(12) . . . . ?
C7 C1 C2 C6 -153.19(11) . . . . ?
C3 C1 C2 C6 97.70(12) . . . . ?
C1 C2 C3 C4 107.98(11) . . . . ?
C6 C2 C3 C4 -2.38(14) . . . . ?
C6 C2 C3 C1 -110.36(12) . . . . ?
C7 C1 C3 C4 154.53(11) . . . . ?
C2 C1 C3 C4 -96.17(12) . . . . ?
C7 C1 C3 C2 -109.31(12) . . . . ?
C2 C3 C4 O1 167.57(12) . . . . ?
C1 C3 C4 O1 -129.42(13) . . . . ?
C2 C3 C4 C5 -11.62(13) . . . . ?
C1 C3 C4 C5 51.38(14) . . . . ?
O1 C4 C5 C6 -158.28(13) . . . . ?
C3 C4 C5 C6 20.92(14) . . . . ?
C1 C2 C6 C5 -51.40(15) . . . . ?
C3 C2 C6 C5 15.06(14) . . . . ?
C4 C5 C6 C2 -21.64(14) . . . . ?
C7 C1 C2B C3B 109.11(12) . . . . ?
C7 C1 C2B C6B -153.19(11) . . . . ?
C3B C1 C2B C6B 97.70(12) . . . . ?
C1 C2B C3B C4B 107.98(11) . . . . ?
C6B C2B C3B C4B -2.38(14) . . . . ?
C6B C2B C3B C1 -110.36(12) . . . . ?
C7 C1 C3B C4B 154.53(11) . . . . ?
C2B C1 C3B C4B -96.17(12) . . . . ?
C7 C1 C3B C2B -109.31(12) . . . . ?
C2B C3B C4B C5B -11.62(13) . . . . ?
C1 C3B C4B C5B 51.38(14) . . . . ?
C3B C4B C5B C6B 20.92(14) . . . . ?
C1 C2B C6B O1B 103(3) . . . . ?
C3B C2B C6B O1B 169(3) . . . . ?
C1 C2B C6B C5B -51.40(15) . . . . ?
C3B C2B C6B C5B 15.06(14) . . . . ?
C4B C5B C6B O1B 178(2) . . . . ?
C4B C5B C6B C2B -21.64(14) . . . . ?
C2 C1 C7 C12 -48.35(17) . . . . ?
C2B C1 C7 C12 -48.35(17) . . . . ?
C3 C1 C7 C12 21.66(18) . . . . ?
C3B C1 C7 C12 21.66(18) . . . . ?
C2 C1 C7 C8 129.98(12) . . . . ?
C2B C1 C7 C8 129.98(12) . . . . ?
C3 C1 C7 C8 -160.01(11) . . . . ?
C3B C1 C7 C8 -160.01(11) . . . . ?
C12 C7 C8 C9 1.33(19) . . . . ?
C1 C7 C8 C9 -177.07(12) . . . . ?
C7 C8 C9 C10 -0.84(19) . . . . ?
C8 C9 C10 C11 -0.66(19) . . . . ?
C8 C9 C10 C13 178.39(12) . . . . ?
C9 C10 C11 C12 1.63(19) . . . . ?
C13 C10 C11 C12 -177.43(12) . . . . ?
C10 C11 C12 C7 -1.1(2) . . . . ?
C8 C7 C12 C11 -0.34(19) . . . . ?
C1 C7 C12 C11 177.98(12) . . . . ?

_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

_audit_block_code                C13H11NO_yv471_ofial
_audit_creation_method           'APEX3 v2018.7-2'
_shelxl_version_number           ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N O'
_chemical_formula_sum            'C13 H11 N O'
_chemical_formula_weight         197.23 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            4 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             416 #?# check!

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_wv638
_database_code_depnum_ccdc_archive 'CCDC 2044219'
loop_
_audit_author_name
_audit_author_address
'Peter Mayer'
;LMU Muenchen
Germany
;

_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;

_chemical_name_common            RNH142F1
_chemical_compound_source        ?
_chemical_absolute_configuration ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.080 #?# in millimeters
_exptl_crystal_size_mid          0.030 #?# in millimeters
_exptl_crystal_size_min          0.030 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
;
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      112.(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (TXS)'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    ?
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_measurement_details      ?
_diffrn_detector_area_resol_mean 7.3910

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   11.6656(4)
_cell_length_b                   9.4061(4)
_cell_length_c                   10.7626(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.797(2)
_cell_angle_gamma                90
_cell_volume                     1170.04(8)
_cell_measurement_temperature    112.(2) #?# in K
_cell_measurement_reflns_used    3795
_cell_measurement_theta_min      2.7920
_cell_measurement_theta_max      27.0609
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  1.00
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_diffrn_reflns_number            11194 #xl
_diffrn_reflns_av_R_equivalents  0.0421 #xl
_diffrn_reflns_av_unetI/netI     0.0367 #xl
_diffrn_reflns_limit_h_min       -14 #xl
_diffrn_reflns_limit_h_max       14 #xl
_diffrn_reflns_limit_k_min       -11 #xl
_diffrn_reflns_limit_k_max       11 #xl
_diffrn_reflns_limit_l_min       -13 #xl
_diffrn_reflns_limit_l_max       13 #xl
_diffrn_reflns_theta_min         3.246 #xl
_diffrn_reflns_theta_max         26.363 #xl
_diffrn_measured_fraction_theta_max 0.998 #xl
_diffrn_reflns_theta_full        25.242 #xl
_diffrn_measured_fraction_theta_full 0.998 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.998 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.998 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.998 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.998 #xl

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14

_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.
;

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_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'

_reflns_number_total             2388 #xl
_reflns_number_gt                1856 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.000 #xl
_reflns_Friedel_fraction_max     . #xl
_reflns_Friedel_fraction_full    . #xl
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+0.5952P] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr #?#
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details ? #xl
_refine_ls_abs_structure_Flack   ? #xl
_refine_ls_number_reflns         2388 #xl
_refine_ls_number_parameters     154 #xl
_refine_ls_number_restraints     0 #xl
_refine_ls_R_factor_all          0.0622 #xl
_refine_ls_R_factor_gt           0.0434 #xl
_refine_ls_wR_factor_ref         0.1005 #xl
_refine_ls_wR_factor_gt          0.0933 #xl
_refine_ls_goodness_of_fit_ref   1.032 #xl
_refine_ls_restrained_S_all      1.032 #xl
_refine_ls_shift/su_max          0.000 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.226 #xl
_refine_diff_density_min         -0.199 #xl
_refine_diff_density_rms         0.042 #xl

_refine_special_details          
;
;

_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'

_computing_publication_material  ?

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 -0.05132(10) 0.36380(13) 0.39951(11) 0.0268(3) Uani 1 1 d . . . . .
O2 O 0.02727(11) 0.52940(13) 0.29661(11) 0.0289(3) Uani 1 1 d . . . . .
N1 N 0.66389(13) 0.36602(18) 0.95272(14) 0.0318(4) Uani 1 1 d . . . . .
C1 C 0.15686(14) 0.35263(17) 0.39032(15) 0.0205(4) Uani 1 1 d . . . . .
C2 C 0.24985(15) 0.4006(2) 0.31534(16) 0.0255(4) Uani 1 1 d . . . . .
H2A H 0.311817 0.331844 0.303840 0.031 Uiso 1 1 calc R U . . .
H2B H 0.226531 0.463335 0.242449 0.031 Uiso 1 1 calc R U . . .
C3 C 0.24952(14) 0.46241(18) 0.44309(15) 0.0222(4) Uani 1 1 d . . . . .
H3 H 0.219949 0.562243 0.442147 0.027 Uiso 1 1 calc R U . . .
C4 C 0.04119(14) 0.42045(18) 0.35694(15) 0.0217(4) Uani 1 1 d . . . . .
C5 C 0.16002(14) 0.20441(17) 0.44420(16) 0.0227(4) Uani 1 1 d . . . . .
H5A H 0.238126 0.183476 0.488708 0.027 Uiso 1 1 calc R U . . .
H5B H 0.141863 0.133913 0.376066 0.027 Uiso 1 1 calc R U . . .
C6 C 0.07108(15) 0.19565(18) 0.53474(16) 0.0257(4) Uani 1 1 d . . . . .
H6A H 0.071592 0.099301 0.571842 0.031 Uiso 1 1 calc R U . . .
H6B H 0.090027 0.265174 0.603517 0.031 Uiso 1 1 calc R U . . .
C7 C -0.04614(15) 0.22745(18) 0.46444(17) 0.0278(4) Uani 1 1 d . . . . .
H7A H -0.067538 0.151045 0.402345 0.033 Uiso 1 1 calc R U . . .
H7B H -0.103721 0.227239 0.524069 0.033 Uiso 1 1 calc R U . . .
C8 C 0.33718(14) 0.42991(17) 0.55293(15) 0.0206(4) Uani 1 1 d . . . . .
C9 C 0.43804(15) 0.35389(18) 0.54323(16) 0.0247(4) Uani 1 1 d . . . . .
H9 H 0.449621 0.314697 0.464536 0.030 Uiso 1 1 calc R U . . .
C10 C 0.52159(15) 0.33433(18) 0.64571(16) 0.0242(4) Uani 1 1 d . . . . .
H10 H 0.590046 0.282517 0.637412 0.029 Uiso 1 1 calc R U . . .
C11 C 0.50463(14) 0.39121(17) 0.76127(15) 0.0210(4) Uani 1 1 d . . . . .
C12 C 0.40296(15) 0.46443(18) 0.77374(16) 0.0241(4) Uani 1 1 d . . . . .
H12 H 0.390563 0.501262 0.853016 0.029 Uiso 1 1 calc R U . . .
C13 C 0.32038(14) 0.48320(18) 0.67047(16) 0.0232(4) Uani 1 1 d . . . . .
H13 H 0.251119 0.533040 0.679320 0.028 Uiso 1 1 calc R U . . .
C14 C 0.59359(15) 0.37645(18) 0.86744(16) 0.0237(4) Uani 1 1 d . . . . .


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 C4 1.339(2) . ?
O1 C7 1.458(2) . ?
O2 C4 1.212(2) . ?
N1 C14 1.149(2) . ?
C1 C4 1.492(2) . ?
C1 C2 1.506(2) . ?
C1 C5 1.508(2) . ?
C1 C3 1.546(2) . ?
C2 C3 1.493(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C8 1.486(2) . ?
C3 H3 1.0000 . ?
C5 C6 1.519(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.500(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.393(2) . ?
C8 C13 1.399(2) . ?
C9 C10 1.382(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(2) . ?
C11 C14 1.442(2) . ?
C12 C13 1.380(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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
C4 O1 C7 122.09(13) . . ?
C4 C1 C2 115.89(14) . . ?
C4 C1 C5 117.51(14) . . ?
C2 C1 C5 120.06(14) . . ?
C4 C1 C3 111.55(14) . . ?
C2 C1 C3 58.56(11) . . ?
C5 C1 C3 119.78(14) . . ?
C3 C2 C1 62.06(11) . . ?
C3 C2 H2A 117.6 . . ?
C1 C2 H2A 117.6 . . ?
C3 C2 H2B 117.6 . . ?
C1 C2 H2B 117.6 . . ?
H2A C2 H2B 114.6 . . ?
C8 C3 C2 124.39(15) . . ?
C8 C3 C1 121.74(14) . . ?
C2 C3 C1 59.38(11) . . ?
C8 C3 H3 113.6 . . ?
C2 C3 H3 113.6 . . ?
C1 C3 H3 113.6 . . ?
O2 C4 O1 117.66(15) . . ?
O2 C4 C1 122.79(16) . . ?
O1 C4 C1 119.48(14) . . ?
C1 C5 C6 108.28(14) . . ?
C1 C5 H5A 110.0 . . ?
C6 C5 H5A 110.0 . . ?
C1 C5 H5B 110.0 . . ?
C6 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C7 C6 C5 108.71(14) . . ?
C7 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
C7 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
O1 C7 C6 113.13(14) . . ?
O1 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
O1 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C13 118.37(15) . . ?
C9 C8 C3 122.89(15) . . ?
C13 C8 C3 118.68(15) . . ?
C10 C9 C8 121.34(16) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 119.44(16) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.12(15) . . ?
C10 C11 C14 119.76(15) . . ?
C12 C11 C14 120.11(15) . . ?
C13 C12 C11 119.74(15) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 120.95(16) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
N1 C14 C11 179.2(2) . . ?

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
C4 C1 C2 C3 100.48(16) . . . . ?
C5 C1 C2 C3 -108.59(17) . . . . ?
C1 C2 C3 C8 109.62(17) . . . . ?
C4 C1 C3 C8 138.08(16) . . . . ?
C2 C1 C3 C8 -113.93(18) . . . . ?
C5 C1 C3 C8 -4.9(2) . . . . ?
C4 C1 C3 C2 -107.99(16) . . . . ?
C5 C1 C3 C2 109.06(17) . . . . ?
C7 O1 C4 O2 175.09(15) . . . . ?
C7 O1 C4 C1 -8.0(2) . . . . ?
C2 C1 C4 O2 -17.2(2) . . . . ?
C5 C1 C4 O2 -168.85(15) . . . . ?
C3 C1 C4 O2 47.3(2) . . . . ?
C2 C1 C4 O1 166.06(14) . . . . ?
C5 C1 C4 O1 14.4(2) . . . . ?
C3 C1 C4 O1 -129.51(15) . . . . ?
C4 C1 C5 C6 -40.39(19) . . . . ?
C2 C1 C5 C6 169.13(14) . . . . ?
C3 C1 C5 C6 100.43(17) . . . . ?
C1 C5 C6 C7 59.85(18) . . . . ?
C4 O1 C7 C6 29.4(2) . . . . ?
C5 C6 C7 O1 -55.47(19) . . . . ?
C2 C3 C8 C9 9.5(2) . . . . ?
C1 C3 C8 C9 81.9(2) . . . . ?
C2 C3 C8 C13 -173.40(16) . . . . ?
C1 C3 C8 C13 -100.99(19) . . . . ?
C13 C8 C9 C10 -1.8(2) . . . . ?
C3 C8 C9 C10 175.30(16) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 1.4(2) . . . . ?
C9 C10 C11 C14 -177.37(16) . . . . ?
C10 C11 C12 C13 -1.5(2) . . . . ?
C14 C11 C12 C13 177.29(16) . . . . ?
C11 C12 C13 C8 -0.1(3) . . . . ?
C9 C8 C13 C12 1.7(2) . . . . ?
C3 C8 C13 C12 -175.50(15) . . . . ?

_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

_audit_block_code                C14H13NO2_wv638_mayr
_audit_creation_method           'APEX3 v2017.3-0'
_shelxl_version_number           ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            4 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             480 #?# check!

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xv559
_database_code_depnum_ccdc_archive 'CCDC 2044221'
loop_
_audit_author_name
_audit_author_address
'Peter Mayer'
;LMU Muenchen
Germany
;

_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;

_chemical_name_common            RNH378
_chemical_compound_source        ?
_chemical_absolute_configuration syn

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.100 #?# in millimeters
_exptl_crystal_size_mid          0.040 #?# in millimeters
_exptl_crystal_size_min          0.020 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
;
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      103.(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (TXS)'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    ?
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_measurement_details      ?
_diffrn_detector_area_resol_mean 7.3910

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   21.9099(11)
_cell_length_b                   6.5137(4)
_cell_length_c                   14.4743(8)
_cell_angle_alpha                90
_cell_angle_beta                 115.663(2)
_cell_angle_gamma                90
_cell_volume                     1861.93(18)
_cell_measurement_temperature    103.(2) #?# in K
_cell_measurement_reflns_used    5076
_cell_measurement_theta_min      2.9029
_cell_measurement_theta_max      26.3594
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  1.00
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_diffrn_reflns_number            10760 #xl
_diffrn_reflns_av_R_equivalents  0.0360 #xl
_diffrn_reflns_av_unetI/netI     0.0431 #xl
_diffrn_reflns_limit_h_min       -27 #xl
_diffrn_reflns_limit_h_max       27 #xl
_diffrn_reflns_limit_k_min       -8 #xl
_diffrn_reflns_limit_k_max       8 #xl
_diffrn_reflns_limit_l_min       -18 #xl
_diffrn_reflns_limit_l_max       17 #xl
_diffrn_reflns_theta_min         3.080 #xl
_diffrn_reflns_theta_max         26.370 #xl
_diffrn_measured_fraction_theta_max 0.997 #xl
_diffrn_reflns_theta_full        25.242 #xl
_diffrn_measured_fraction_theta_full 0.996 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.997 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.996 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.992 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.995 #xl

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
_space_group_IT_number           5

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

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'

_reflns_number_total             3790 #xl
_reflns_number_gt                3410 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.823 #xl
_reflns_Friedel_fraction_max     0.986 #xl
_reflns_Friedel_fraction_full    0.994 #xl
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+1.4361P] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr #?#
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details 
;

Flack x determined using 1338 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(6) #xl
_refine_ls_number_reflns         3790 #xl
_refine_ls_number_parameters     246 #xl
_refine_ls_number_restraints     1 #xl
_refine_ls_R_factor_all          0.0489 #xl
_refine_ls_R_factor_gt           0.0423 #xl
_refine_ls_wR_factor_ref         0.1041 #xl
_refine_ls_wR_factor_gt          0.1005 #xl
_refine_ls_goodness_of_fit_ref   1.070 #xl
_refine_ls_restrained_S_all      1.069 #xl
_refine_ls_shift/su_max          0.000 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.177 #xl
_refine_diff_density_min         -0.185 #xl
_refine_diff_density_rms         0.044 #xl

_refine_special_details          
;
;

_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'

_computing_publication_material  ?

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
C1 C -0.04928(15) 0.3140(5) 0.0656(2) 0.0244(7) Uani 1 1 d . . . . .
C2 C -0.00876(15) 0.1579(5) 0.1359(2) 0.0221(7) Uani 1 1 d . . . . .
C3 C -0.01132(15) -0.0441(5) 0.1034(2) 0.0235(7) Uani 1 1 d . . . . .
H3 H -0.044759 -0.084406 0.037886 0.028 Uiso 1 1 calc R U . . .
C4 C 0.03479(15) -0.1863(5) 0.1663(2) 0.0224(7) Uani 1 1 d . . . . .
H4 H 0.033241 -0.323342 0.142933 0.027 Uiso 1 1 calc R U . . .
C5 C 0.08356(14) -0.1321(5) 0.2637(2) 0.0196(6) Uani 1 1 d . . . . .
C6 C 0.08229(15) 0.0679(5) 0.2983(2) 0.0225(7) Uani 1 1 d . . . . .
H6 H 0.112828 0.105003 0.366234 0.027 Uiso 1 1 calc R U . . .
C7 C 0.03733(15) 0.2119(5) 0.2353(2) 0.0246(7) Uani 1 1 d . . . . .
H7 H 0.037704 0.347789 0.259379 0.030 Uiso 1 1 calc R U . . .
C8 C 0.13642(14) -0.2785(5) 0.3304(2) 0.0203(6) Uani 1 1 d . . . . .
H8 H 0.133604 -0.317125 0.395271 0.024 Uiso 1 1 calc R U . . .
C9 C 0.16439(15) -0.4418(5) 0.2864(2) 0.0232(7) Uani 1 1 d . . . . .
H9A H 0.146182 -0.450392 0.210846 0.028 Uiso 1 1 calc R U . . .
H9AB H 0.176479 -0.575468 0.322422 0.028 Uiso 1 1 calc R U . . .
C10 C 0.20800(14) -0.2561(5) 0.3395(2) 0.0173(6) Uani 1 1 d . . . . .
C11 C 0.26426(15) -0.2981(5) 0.4411(2) 0.0204(6) Uani 1 1 d . . . . .
C12 C 0.31002(14) -0.0961(5) 0.3554(2) 0.0182(6) Uani 1 1 d . . . . .
H12 H 0.331420 -0.171696 0.316912 0.022 Uiso 1 1 calc R U . . .
C13 C 0.34304(14) 0.1121(5) 0.3871(2) 0.0211(6) Uani 1 1 d . . . . .
H13 H 0.311188 0.226005 0.382172 0.025 Uiso 1 1 calc R U . . .
C14 C 0.40268(16) 0.1759(5) 0.3724(2) 0.0251(7) Uani 1 1 d . . . . .
C15 C 0.40670(18) 0.4001(6) 0.3491(3) 0.0308(8) Uani 1 1 d . . . . .
H15A H 0.454591 0.439882 0.371085 0.037 Uiso 1 1 calc R U . . .
H15B H 0.387964 0.485097 0.387417 0.037 Uiso 1 1 calc R U . . .
C16 C 0.36610(18) 0.4384(5) 0.2327(3) 0.0323(8) Uani 1 1 d . . . . .
H16A H 0.363008 0.587938 0.219077 0.039 Uiso 1 1 calc R U . . .
H16B H 0.390079 0.374895 0.195603 0.039 Uiso 1 1 calc R U . . .
C17 C 0.29632(18) 0.3501(5) 0.1941(3) 0.0278(7) Uani 1 1 d . . . . .
H17 H 0.266133 0.419103 0.214921 0.033 Uiso 1 1 calc R U . . .
C18 C 0.27139(16) 0.1868(5) 0.1343(2) 0.0246(7) Uani 1 1 d . . . . .
C19 C 0.20401(15) 0.0971(5) 0.1176(2) 0.0254(7) Uani 1 1 d . . . . .
H19A H 0.176809 0.075506 0.043138 0.030 Uiso 1 1 calc R U . . .
H19B H 0.179788 0.198844 0.140319 0.030 Uiso 1 1 calc R U . . .
C20 C 0.20742(15) -0.1065(5) 0.1730(2) 0.0224(6) Uani 1 1 d . . . . .
H20A H 0.238162 -0.200808 0.159754 0.027 Uiso 1 1 calc R U . . .
H20B H 0.161792 -0.169440 0.143109 0.027 Uiso 1 1 calc R U . . .
C21 C 0.23189(14) -0.0884(5) 0.2897(2) 0.0178(6) Uani 1 1 d . . . . .
H21 H 0.215340 0.045841 0.303653 0.021 Uiso 1 1 calc R U . . .
C22 C 0.44088(16) 0.0309(6) 0.3360(3) 0.0312(8) Uani 1 1 d . . . . .
H22A H 0.488733 0.070614 0.365673 0.047 Uiso 1 1 calc R U . . .
H22B H 0.422048 0.036535 0.261039 0.047 Uiso 1 1 calc R U . . .
H22C H 0.436818 -0.109100 0.357457 0.047 Uiso 1 1 calc R U . . .
C23 C 0.30605(18) 0.0768(6) 0.0794(3) 0.0346(8) Uani 1 1 d . . . . .
H23A H 0.275843 0.071416 0.005983 0.052 Uiso 1 1 calc R U . . .
H23B H 0.317350 -0.063131 0.106344 0.052 Uiso 1 1 calc R U . . .
H23C H 0.347629 0.150196 0.090117 0.052 Uiso 1 1 calc R U . . .
N1 N -0.07844(14) 0.4416(5) 0.0080(2) 0.0303(7) Uani 1 1 d . . . . .
O1 O 0.32154(10) -0.2090(3) 0.44857(15) 0.0218(5) Uani 1 1 d . . . . .
O2 O 0.26356(11) -0.3988(4) 0.51046(16) 0.0289(5) Uani 1 1 d . . . . .
O3 O 0.40846(11) 0.1257(4) 0.47372(16) 0.0284(5) Uani 1 1 d . . . . .


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
C1 N1 1.154(4) . ?
C1 C2 1.440(5) . ?
C2 C3 1.390(4) . ?
C2 C7 1.398(4) . ?
C3 C4 1.383(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(5) . ?
C5 C8 1.488(4) . ?
C6 C7 1.380(5) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.500(4) . ?
C8 C10 1.523(4) . ?
C8 H8 1.0000 . ?
C9 C10 1.527(4) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 C11 1.479(4) . ?
C10 C21 1.520(4) . ?
C11 O2 1.204(4) . ?
C11 O1 1.344(4) . ?
C12 O1 1.458(3) . ?
C12 C13 1.512(4) . ?
C12 C21 1.558(4) . ?
C12 H12 1.0000 . ?
C13 O3 1.442(3) . ?
C13 C14 1.472(4) . ?
C13 H13 1.0000 . ?
C14 O3 1.454(4) . ?
C14 C22 1.501(5) . ?
C14 C15 1.510(5) . ?
C15 C16 1.547(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.497(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.330(5) . ?
C17 H17 0.9500 . ?
C18 C23 1.498(4) . ?
C18 C19 1.507(5) . ?
C19 C20 1.535(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.540(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
N1 C1 C2 175.8(3) . . ?
C3 C2 C7 119.5(3) . . ?
C3 C2 C1 120.5(3) . . ?
C7 C2 C1 119.9(3) . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 118.2(3) . . ?
C4 C5 C8 122.2(3) . . ?
C6 C5 C8 119.6(3) . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C5 C8 C9 121.7(3) . . ?
C5 C8 C10 118.5(2) . . ?
C9 C8 C10 60.67(19) . . ?
C5 C8 H8 115.0 . . ?
C9 C8 H8 115.0 . . ?
C10 C8 H8 115.0 . . ?
C8 C9 C10 60.41(19) . . ?
C8 C9 H9A 117.7 . . ?
C10 C9 H9A 117.7 . . ?
C8 C9 H9AB 117.7 . . ?
C10 C9 H9AB 117.7 . . ?
H9A C9 H9AB 114.9 . . ?
C11 C10 C21 107.1(2) . . ?
C11 C10 C8 116.8(2) . . ?
C21 C10 C8 125.5(2) . . ?
C11 C10 C9 115.1(2) . . ?
C21 C10 C9 126.9(2) . . ?
C8 C10 C9 58.92(19) . . ?
O2 C11 O1 121.1(3) . . ?
O2 C11 C10 128.6(3) . . ?
O1 C11 C10 110.3(2) . . ?
O1 C12 C13 107.7(2) . . ?
O1 C12 C21 106.6(2) . . ?
C13 C12 C21 114.3(2) . . ?
O1 C12 H12 109.4 . . ?
C13 C12 H12 109.4 . . ?
C21 C12 H12 109.4 . . ?
O3 C13 C14 59.88(19) . . ?
O3 C13 C12 118.9(3) . . ?
C14 C13 C12 123.2(3) . . ?
O3 C13 H13 114.6 . . ?
C14 C13 H13 114.6 . . ?
C12 C13 H13 114.6 . . ?
O3 C14 C13 59.03(18) . . ?
O3 C14 C22 113.2(3) . . ?
C13 C14 C22 122.5(3) . . ?
O3 C14 C15 117.0(3) . . ?
C13 C14 C15 116.5(3) . . ?
C22 C14 C15 115.8(3) . . ?
C14 C15 C16 109.7(3) . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 C15 110.9(3) . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.0 . . ?
C18 C17 C16 128.0(3) . . ?
C18 C17 H17 116.0 . . ?
C16 C17 H17 116.0 . . ?
C17 C18 C23 124.6(3) . . ?
C17 C18 C19 120.8(3) . . ?
C23 C18 C19 114.6(3) . . ?
C18 C19 C20 115.4(3) . . ?
C18 C19 H19A 108.4 . . ?
C20 C19 H19A 108.4 . . ?
C18 C19 H19B 108.4 . . ?
C20 C19 H19B 108.4 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 C21 115.0(3) . . ?
C19 C20 H20A 108.5 . . ?
C21 C20 H20A 108.5 . . ?
C19 C20 H20B 108.5 . . ?
C21 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C10 C21 C20 115.9(2) . . ?
C10 C21 C12 101.6(2) . . ?
C20 C21 C12 115.8(2) . . ?
C10 C21 H21 107.7 . . ?
C20 C21 H21 107.7 . . ?
C12 C21 H21 107.7 . . ?
C14 C22 H22A 109.5 . . ?
C14 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C14 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C11 O1 C12 111.2(2) . . ?
C13 O3 C14 61.09(19) . . ?

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
C7 C2 C3 C4 -4.8(4) . . . . ?
C1 C2 C3 C4 170.4(3) . . . . ?
C2 C3 C4 C5 1.3(4) . . . . ?
C3 C4 C5 C6 3.4(4) . . . . ?
C3 C4 C5 C8 -176.1(3) . . . . ?
C4 C5 C6 C7 -4.7(4) . . . . ?
C8 C5 C6 C7 174.9(3) . . . . ?
C5 C6 C7 C2 1.3(5) . . . . ?
C3 C2 C7 C6 3.5(5) . . . . ?
C1 C2 C7 C6 -171.7(3) . . . . ?
C4 C5 C8 C9 31.6(4) . . . . ?
C6 C5 C8 C9 -148.0(3) . . . . ?
C4 C5 C8 C10 103.0(3) . . . . ?
C6 C5 C8 C10 -76.6(4) . . . . ?
C5 C8 C9 C10 107.3(3) . . . . ?
C5 C8 C10 C11 143.1(3) . . . . ?
C9 C8 C10 C11 -104.5(3) . . . . ?
C5 C8 C10 C21 3.1(4) . . . . ?
C9 C8 C10 C21 115.5(3) . . . . ?
C5 C8 C10 C9 -112.4(3) . . . . ?
C8 C9 C10 C11 107.4(3) . . . . ?
C8 C9 C10 C21 -113.3(3) . . . . ?
C21 C10 C11 O2 169.0(3) . . . . ?
C8 C10 C11 O2 22.2(5) . . . . ?
C9 C10 C11 O2 -44.1(4) . . . . ?
C21 C10 C11 O1 -12.4(3) . . . . ?
C8 C10 C11 O1 -159.3(3) . . . . ?
C9 C10 C11 O1 134.4(3) . . . . ?
O1 C12 C13 O3 41.0(3) . . . . ?
C21 C12 C13 O3 159.2(2) . . . . ?
O1 C12 C13 C14 112.1(3) . . . . ?
C21 C12 C13 C14 -129.7(3) . . . . ?
C12 C13 C14 O3 -106.8(3) . . . . ?
O3 C13 C14 C22 99.4(3) . . . . ?
C12 C13 C14 C22 -7.4(5) . . . . ?
O3 C13 C14 C15 -107.0(3) . . . . ?
C12 C13 C14 C15 146.2(3) . . . . ?
O3 C14 C15 C16 -151.8(3) . . . . ?
C13 C14 C15 C16 -84.9(3) . . . . ?
C22 C14 C15 C16 70.5(4) . . . . ?
C14 C15 C16 C17 50.6(4) . . . . ?
C15 C16 C17 C18 -109.1(4) . . . . ?
C16 C17 C18 C23 -10.3(5) . . . . ?
C16 C17 C18 C19 169.3(3) . . . . ?
C17 C18 C19 C20 -106.3(4) . . . . ?
C23 C18 C19 C20 73.3(3) . . . . ?
C18 C19 C20 C21 73.1(3) . . . . ?
C11 C10 C21 C20 143.7(3) . . . . ?
C8 C10 C21 C20 -73.2(4) . . . . ?
C9 C10 C21 C20 1.9(4) . . . . ?
C11 C10 C21 C12 17.3(3) . . . . ?
C8 C10 C21 C12 160.4(3) . . . . ?
C9 C10 C21 C12 -124.5(3) . . . . ?
C19 C20 C21 C10 154.3(3) . . . . ?
C19 C20 C21 C12 -86.8(3) . . . . ?
O1 C12 C21 C10 -16.6(3) . . . . ?
C13 C12 C21 C10 -135.5(2) . . . . ?
O1 C12 C21 C20 -143.1(3) . . . . ?
C13 C12 C21 C20 98.1(3) . . . . ?
O2 C11 O1 C12 179.9(3) . . . . ?
C10 C11 O1 C12 1.2(3) . . . . ?
C13 C12 O1 C11 133.3(2) . . . . ?
C21 C12 O1 C11 10.3(3) . . . . ?
C12 C13 O3 C14 113.8(3) . . . . ?
C22 C14 O3 C13 -115.2(3) . . . . ?
C15 C14 O3 C13 106.2(3) . . . . ?

_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

_audit_block_code                C23H25NO3_xv559_ofial
_audit_creation_method           'APEX3 v2018.7-2'
_shelxl_version_number           ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H25 N O3'
_chemical_formula_sum            'C23 H25 N O3'
_chemical_formula_weight         363.44 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            4 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             776 #?# check!


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vv592
_database_code_depnum_ccdc_archive 'CCDC 2044220'
loop_
_audit_author_name
_audit_author_address
'Peter Mayer'
;LMU Muenchen
Germany
;

_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;

_chemical_name_common            RM445-4-8
_chemical_compound_source        ?
_chemical_absolute_configuration ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.080 #?# in millimeters
_exptl_crystal_size_mid          0.060 #?# in millimeters
_exptl_crystal_size_min          0.030 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
;
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      103.(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (TXS)'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    ?
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_measurement_details      ?
_diffrn_detector_area_resol_mean 7.4074

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   7.3211(2)
_cell_length_b                   7.9973(2)
_cell_length_c                   8.7918(3)
_cell_angle_alpha                69.1780(10)
_cell_angle_beta                 74.1170(10)
_cell_angle_gamma                83.7140(10)
_cell_volume                     462.72(2)
_cell_measurement_temperature    103.(2) #?# in K
_cell_measurement_reflns_used    7233
_cell_measurement_theta_min      2.8930
_cell_measurement_theta_max      27.1291
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.9226
_exptl_absorpt_correction_T_max  0.9705
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_diffrn_reflns_number            8722 #xl
_diffrn_reflns_av_R_equivalents  0.0244 #xl
_diffrn_reflns_av_unetI/netI     0.0205 #xl
_diffrn_reflns_limit_h_min       -9 #xl
_diffrn_reflns_limit_h_max       9 #xl
_diffrn_reflns_limit_k_min       -10 #xl
_diffrn_reflns_limit_k_max       10 #xl
_diffrn_reflns_limit_l_min       -11 #xl
_diffrn_reflns_limit_l_max       11 #xl
_diffrn_reflns_theta_min         3.345 #xl
_diffrn_reflns_theta_max         27.099 #xl
_diffrn_measured_fraction_theta_max 0.994 #xl
_diffrn_reflns_theta_full        25.242 #xl
_diffrn_measured_fraction_theta_full 0.994 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.994 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.994 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.994 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.994 #xl

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_reflns_number_total             2031 #xl
_reflns_number_gt                1867 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.000 #xl
_reflns_Friedel_fraction_max     . #xl
_reflns_Friedel_fraction_full    . #xl
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0274P)²+0.2230P] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr #?#
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details ? #xl
_refine_ls_abs_structure_Flack   ? #xl
_refine_ls_number_reflns         2031 #xl
_refine_ls_number_parameters     111 #xl
_refine_ls_number_restraints     0 #xl
_refine_ls_R_factor_all          0.0299 #xl
_refine_ls_R_factor_gt           0.0266 #xl
_refine_ls_wR_factor_ref         0.0704 #xl
_refine_ls_wR_factor_gt          0.0679 #xl
_refine_ls_goodness_of_fit_ref   1.065 #xl
_refine_ls_restrained_S_all      1.065 #xl
_refine_ls_shift/su_max          0.000 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.295 #xl
_refine_diff_density_min         -0.192 #xl
_refine_diff_density_rms         0.042 #xl

_refine_special_details          
;
;

_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 807)'

_computing_publication_material  ?

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 0.71638(4) 0.87135(4) -0.01904(4) 0.01966(10) Uani 1 1 d . . . . .
N1 N 1.04059(16) 0.16649(14) 0.57166(15) 0.0251(2) Uani 1 1 d . . . . .
C1 C 0.60882(17) 0.77742(16) 0.20614(15) 0.0183(2) Uani 1 1 d . . . . .
H1A H 0.6740 0.8254 0.2665 0.022 Uiso 1 1 calc R U . . .
H1B H 0.4740 0.8163 0.2293 0.022 Uiso 1 1 calc R U . . .
C2 C 0.61912(16) 0.57617(15) 0.27329(14) 0.0156(2) Uani 1 1 d . . . . .
C3 C 0.49254(16) 0.46928(16) 0.25347(14) 0.0165(2) Uani 1 1 d . . . . .
C4 C 0.51368(17) 0.28376(16) 0.31422(15) 0.0182(2) Uani 1 1 d . . . . .
H4 H 0.4290 0.2117 0.3002 0.022 Uiso 1 1 calc R U . . .
C5 C 0.65491(17) 0.20136(16) 0.39462(15) 0.0174(2) Uani 1 1 d . . . . .
H5 H 0.6677 0.0747 0.4344 0.021 Uiso 1 1 calc R U . . .
C6 C 0.77811(16) 0.30805(15) 0.41601(14) 0.0159(2) Uani 1 1 d . . . . .
C7 C 0.75967(16) 0.49433(15) 0.35551(14) 0.0163(2) Uani 1 1 d . . . . .
H7 H 0.8440 0.5658 0.3707 0.020 Uiso 1 1 calc R U . . .
C8 C 0.33383(17) 0.55203(17) 0.17074(16) 0.0212(3) Uani 1 1 d . . . . .
H8A H 0.2722 0.4591 0.1545 0.032 Uiso 1 1 calc R U . . .
H8B H 0.3855 0.6431 0.0615 0.032 Uiso 1 1 calc R U . . .
H8C H 0.2405 0.6077 0.2425 0.032 Uiso 1 1 calc R U . . .
C9 C 0.92439(17) 0.22752(15) 0.50200(15) 0.0178(2) Uani 1 1 d . . . . .
C10 C 0.95868(18) 0.79601(17) -0.02550(17) 0.0246(3) Uani 1 1 d . . . . .
H10A H 1.0394 0.8538 -0.1384 0.037 Uiso 1 1 calc R U . . .
H10B H 0.9661 0.6659 0.0017 0.037 Uiso 1 1 calc R U . . .
H10C H 1.0024 0.8273 0.0567 0.037 Uiso 1 1 calc R U . . .


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 C10 1.8023(13) . ?
S1 C1 1.8228(12) . ?
N1 C9 1.1484(16) . ?
C1 C2 1.5056(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C7 1.3903(16) . ?
C2 C3 1.4098(17) . ?
C3 C4 1.3936(17) . ?
C3 C8 1.5063(16) . ?
C4 C5 1.3866(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3973(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.3973(16) . ?
C6 C9 1.4419(16) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
C10 S1 C1 100.28(6) . . ?
C2 C1 S1 113.04(8) . . ?
C2 C1 H1A 109.0 . . ?
S1 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
S1 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C7 C2 C3 119.37(11) . . ?
C7 C2 C1 118.58(10) . . ?
C3 C2 C1 122.05(11) . . ?
C4 C3 C2 119.07(11) . . ?
C4 C3 C8 119.75(11) . . ?
C2 C3 C8 121.17(11) . . ?
C5 C4 C3 121.83(11) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 118.78(11) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 120.26(11) . . ?
C7 C6 C9 119.22(10) . . ?
C5 C6 C9 120.52(10) . . ?
C2 C7 C6 120.67(11) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C6 178.51(13) . . ?
S1 C10 H10A 109.5 . . ?
S1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
S1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
C10 S1 C1 C2 -62.52(10) . . . . ?
S1 C1 C2 C7 100.06(11) . . . . ?
S1 C1 C2 C3 -79.17(13) . . . . ?
C7 C2 C3 C4 -1.17(17) . . . . ?
C1 C2 C3 C4 178.06(10) . . . . ?
C7 C2 C3 C8 177.79(10) . . . . ?
C1 C2 C3 C8 -2.98(17) . . . . ?
C2 C3 C4 C5 0.45(17) . . . . ?
C8 C3 C4 C5 -178.53(11) . . . . ?
C3 C4 C5 C6 0.48(18) . . . . ?
C4 C5 C6 C7 -0.68(17) . . . . ?
C4 C5 C6 C9 178.72(11) . . . . ?
C3 C2 C7 C6 0.98(17) . . . . ?
C1 C2 C7 C6 -178.27(10) . . . . ?
C5 C6 C7 C2 -0.05(17) . . . . ?
C9 C6 C7 C2 -179.46(11) . . . . ?

_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

_audit_block_code                C10H11NS_vv592_mayr
_audit_creation_method           'APEX3 v2016.9-0'
_shelxl_version_number           ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 N S'
_chemical_formula_sum            'C10 H11 N S'
_chemical_formula_weight         177.26 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            2 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             188 #?# check!

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vv629
_database_code_depnum_ccdc_archive 'CCDC 2044218'
loop_
_audit_author_name
_audit_author_address
'Peter Mayer'
;LMU Muenchen
Germany
;

_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;

_chemical_name_common            RM444
_chemical_compound_source        ?
_chemical_absolute_configuration ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.100 #?# in millimeters
_exptl_crystal_size_mid          0.080 #?# in millimeters
_exptl_crystal_size_min          0.050 #?# in millimeters
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_meas      ?
_exptl_special_details           
;
;
_audit_creation_date             ? #?# style: 18-Aug-1998

_diffrn_ambient_temperature      103.(2) #?# in K
_diffrn_source_type              'Bruker TXS'
_diffrn_source_power             2.5 #?# in kW
_diffrn_source_voltage           50 #?# in kV
_diffrn_source_current           50 #?# in mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (TXS)'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_collimation    ?
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_measurement_details      ?
_diffrn_detector_area_resol_mean 7.4074

_diffrn_special_details          ?
_diffrn_orient_matrix_type       ?
_diffrn_orient_matrix_UB_11      ?
_diffrn_orient_matrix_UB_12      ?
_diffrn_orient_matrix_UB_13      ?
_diffrn_orient_matrix_UB_21      ?
_diffrn_orient_matrix_UB_22      ?
_diffrn_orient_matrix_UB_23      ?
_diffrn_orient_matrix_UB_31      ?
_diffrn_orient_matrix_UB_32      ?
_diffrn_orient_matrix_UB_33      ?

_cell_length_a                   12.1957(10)
_cell_length_b                   7.1469(5)
_cell_length_c                   12.4085(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.197(3)
_cell_angle_gamma                90
_cell_volume                     1043.72(15)
_cell_measurement_temperature    103.(2) #?# in K
_cell_measurement_reflns_used    6941
_cell_measurement_theta_min      3.3349
_cell_measurement_theta_max      26.4637
_cell_special_details            ?

_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.99
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;

_diffrn_reflns_number            14056 #xl
_diffrn_reflns_av_R_equivalents  0.0402 #xl
_diffrn_reflns_av_unetI/netI     0.0254 #xl
_diffrn_reflns_limit_h_min       -15 #xl
_diffrn_reflns_limit_h_max       15 #xl
_diffrn_reflns_limit_k_min       -8 #xl
_diffrn_reflns_limit_k_max       8 #xl
_diffrn_reflns_limit_l_min       -15 #xl
_diffrn_reflns_limit_l_max       15 #xl
_diffrn_reflns_theta_min         3.320 #xl
_diffrn_reflns_theta_max         26.371 #xl
_diffrn_measured_fraction_theta_max 0.996 #xl
_diffrn_reflns_theta_full        25.242 #xl
_diffrn_measured_fraction_theta_full 0.996 #xl
_diffrn_reflns_Laue_measured_fraction_max 0.996 #xl
_diffrn_reflns_Laue_measured_fraction_full 0.996 #xl
_diffrn_reflns_point_group_measured_fraction_max 0.996 #xl
_diffrn_reflns_point_group_measured_fraction_full 0.996 #xl

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14

_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.
;

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_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'

_reflns_number_total             2124 #xl
_reflns_number_gt                1670 #xl
_reflns_threshold_expression     'I > 2σ(I)' #xl
_reflns_Friedel_coverage         0.000 #xl
_reflns_Friedel_fraction_max     . #xl
_reflns_Friedel_fraction_full    . #xl
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_refine_ls_structure_factor_coef Fsqd #xl
_refine_ls_matrix_type           full #xl
_refine_ls_weighting_scheme      calc #xl
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0342P)²+0.9886P] where P=(Fo²+2Fc²)/3' #xl
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr #?#
_refine_ls_extinction_method     none #xl
_refine_ls_extinction_coef       . #xl
_refine_ls_abs_structure_details ? #xl
_refine_ls_abs_structure_Flack   ? #xl
_refine_ls_number_reflns         2124 #xl
_refine_ls_number_parameters     145 #xl
_refine_ls_number_restraints     0 #xl
_refine_ls_R_factor_all          0.0615 #xl
_refine_ls_R_factor_gt           0.0431 #xl
_refine_ls_wR_factor_ref         0.1092 #xl
_refine_ls_wR_factor_gt          0.0969 #xl
_refine_ls_goodness_of_fit_ref   1.054 #xl
_refine_ls_restrained_S_all      1.054 #xl
_refine_ls_shift/su_max          0.000 #xl
_refine_ls_shift/su_mean         0.000 #xl
_refine_diff_density_max         0.181 #xl
_refine_diff_density_min         -0.261 #xl
_refine_diff_density_rms         0.049 #xl

_refine_special_details          
;
;

_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 807)'

_computing_publication_material  ?

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 0.66549(11) 0.94043(18) 0.14363(11) 0.0261(3) Uani 1 1 d . . . . .
O2 O 0.49941(11) 1.08961(18) 0.12096(11) 0.0276(3) Uani 1 1 d . . . . .
N1 N 0.37415(14) 0.0737(2) 0.58560(14) 0.0327(4) Uani 1 1 d . . . . .
C1 C 0.55252(15) 0.9453(3) 0.13700(14) 0.0224(4) Uani 1 1 d . . . . .
C2 C 0.51151(15) 0.7531(2) 0.15136(15) 0.0210(4) Uani 1 1 d . . . . .
C3 C 0.61629(15) 0.6311(3) 0.18826(16) 0.0237(4) Uani 1 1 d . . . . .
H3A H 0.6046 0.5076 0.1509 0.028 Uiso 1 1 calc R U . . .
H3B H 0.6382 0.6128 0.2702 0.028 Uiso 1 1 calc R U . . .
C4 C 0.70495(17) 0.7470(3) 0.15033(19) 0.0311(5) Uani 1 1 d . . . . .
H4A H 0.7802 0.7356 0.2047 0.037 Uiso 1 1 calc R U . . .
H4B H 0.7115 0.7035 0.0765 0.037 Uiso 1 1 calc R U . . .
C5 C 0.40050(15) 0.6939(3) 0.07218(15) 0.0247(4) Uani 1 1 d . . . . .
H5A H 0.3619 0.7843 0.0141 0.030 Uiso 1 1 calc R U . . .
H5B H 0.3924 0.5612 0.0486 0.030 Uiso 1 1 calc R U . . .
C6 C 0.40317(15) 0.7375(3) 0.19173(15) 0.0223(4) Uani 1 1 d . . . . .
H6 H 0.3682 0.8603 0.2026 0.027 Uiso 1 1 calc R U . . .
C7 C 0.39355(14) 0.5907(2) 0.27372(14) 0.0211(4) Uani 1 1 d . . . . .
C8 C 0.42330(15) 0.4043(3) 0.26196(15) 0.0242(4) Uani 1 1 d . . . . .
H8 H 0.4474 0.3682 0.1981 0.029 Uiso 1 1 calc R U . . .
C9 C 0.41819(15) 0.2710(3) 0.34193(15) 0.0243(4) Uani 1 1 d . . . . .
H9 H 0.4397 0.1452 0.3333 0.029 Uiso 1 1 calc R U . . .
C10 C 0.38124(14) 0.3230(3) 0.43507(15) 0.0222(4) Uani 1 1 d . . . . .
C11 C 0.34879(15) 0.5073(3) 0.44727(15) 0.0240(4) Uani 1 1 d . . . . .
H11 H 0.3223 0.5421 0.5099 0.029 Uiso 1 1 calc R U . . .
C12 C 0.35546(14) 0.6393(3) 0.36751(15) 0.0225(4) Uani 1 1 d . . . . .
H12 H 0.3339 0.7649 0.3764 0.027 Uiso 1 1 calc R U . . .
C13 C 0.37737(15) 0.1842(3) 0.51880(16) 0.0249(4) Uani 1 1 d . . . . .


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 1.359(2) . ?
O1 C4 1.459(2) . ?
O2 C1 1.207(2) . ?
N1 C13 1.153(2) . ?
C1 C2 1.488(2) . ?
C2 C5 1.510(2) . ?
C2 C3 1.515(2) . ?
C2 C6 1.535(2) . ?
C3 C4 1.531(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.508(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.488(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.398(3) . ?
C7 C12 1.405(2) . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.395(3) . ?
C10 C13 1.446(3) . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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 O1 C4 109.97(14) . . ?
O2 C1 O1 121.57(17) . . ?
O2 C1 C2 128.76(17) . . ?
O1 C1 C2 109.67(15) . . ?
C1 C2 C5 116.93(15) . . ?
C1 C2 C3 106.49(15) . . ?
C5 C2 C3 125.22(16) . . ?
C1 C2 C6 116.81(15) . . ?
C5 C2 C6 59.36(11) . . ?
C3 C2 C6 126.13(15) . . ?
C2 C3 C4 101.76(15) . . ?
C2 C3 H3A 111.4 . . ?
C4 C3 H3A 111.4 . . ?
C2 C3 H3B 111.4 . . ?
C4 C3 H3B 111.4 . . ?
H3A C3 H3B 109.3 . . ?
O1 C4 C3 106.32(14) . . ?
O1 C4 H4A 110.5 . . ?
C3 C4 H4A 110.5 . . ?
O1 C4 H4B 110.5 . . ?
C3 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C6 C5 C2 61.14(12) . . ?
C6 C5 H5A 117.7 . . ?
C2 C5 H5A 117.7 . . ?
C6 C5 H5B 117.7 . . ?
C2 C5 H5B 117.7 . . ?
H5A C5 H5B 114.8 . . ?
C7 C6 C5 122.80(16) . . ?
C7 C6 C2 120.22(15) . . ?
C5 C6 C2 59.50(11) . . ?
C7 C6 H6 114.5 . . ?
C5 C6 H6 114.5 . . ?
C2 C6 H6 114.5 . . ?
C8 C7 C12 118.25(17) . . ?
C8 C7 C6 122.11(16) . . ?
C12 C7 C6 119.63(16) . . ?
C9 C8 C7 121.17(17) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 119.55(17) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.25(17) . . ?
C11 C10 C13 120.41(17) . . ?
C9 C10 C13 119.34(17) . . ?
C12 C11 C10 119.61(17) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C7 121.16(17) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
N1 C13 C10 179.9(2) . . ?

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
C4 O1 C1 O2 -173.45(17) . . . . ?
C4 O1 C1 C2 6.13(19) . . . . ?
O2 C1 C2 C5 43.8(3) . . . . ?
O1 C1 C2 C5 -135.78(16) . . . . ?
O2 C1 C2 C3 -170.67(18) . . . . ?
O1 C1 C2 C3 9.80(19) . . . . ?
O2 C1 C2 C6 -23.7(3) . . . . ?
O1 C1 C2 C6 156.79(14) . . . . ?
C1 C2 C3 C4 -20.30(18) . . . . ?
C5 C2 C3 C4 121.61(18) . . . . ?
C6 C2 C3 C4 -163.29(17) . . . . ?
C1 O1 C4 C3 -19.5(2) . . . . ?
C2 C3 C4 O1 23.89(19) . . . . ?
C1 C2 C5 C6 -106.69(17) . . . . ?
C3 C2 C5 C6 114.88(19) . . . . ?
C2 C5 C6 C7 -108.38(18) . . . . ?
C1 C2 C6 C7 -140.51(17) . . . . ?
C5 C2 C6 C7 112.61(19) . . . . ?
C3 C2 C6 C7 -0.8(3) . . . . ?
C1 C2 C6 C5 106.88(18) . . . . ?
C3 C2 C6 C5 -113.4(2) . . . . ?
C5 C6 C7 C8 24.4(3) . . . . ?
C2 C6 C7 C8 -46.7(2) . . . . ?
C5 C6 C7 C12 -156.80(16) . . . . ?
C2 C6 C7 C12 132.07(17) . . . . ?
C12 C7 C8 C9 -1.6(3) . . . . ?
C6 C7 C8 C9 177.27(16) . . . . ?
C7 C8 C9 C10 0.9(3) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C8 C9 C10 C13 -179.26(16) . . . . ?
C9 C10 C11 C12 -1.2(3) . . . . ?
C13 C10 C11 C12 178.56(16) . . . . ?
C10 C11 C12 C7 0.5(3) . . . . ?
C8 C7 C12 C11 0.8(3) . . . . ?
C6 C7 C12 C11 -178.01(16) . . . . ?

_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

_audit_block_code                C13H11NO2_vv629_mayr
_audit_creation_method           'APEX3 v2016.9-0'
_shelxl_version_number           ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 N O2'
_chemical_formula_sum            'C13 H11 N O2'
_chemical_formula_weight         213.23 #?# (Cohen, 1996)
_chemical_melting_point          ? #?# in K!

_cell_formula_units_Z            4 #?# adjust to _chemical_formula_[]

_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             448 #?# check!

