# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 1957957'
loop_
_audit_author_name
_audit_author_address
'Borodina Tatiana'
'Favorsky Irkutsk Institute of Chemistry Siberian Division of the Russian Academy of Science'
_audit_update_record             
;
2019-10-08 deposited with the CCDC.	2020-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'3-methyl-6-phenylpyrrolo[1,2-a]pyrazine 2-oxide hydrochloride'
_chemical_name_common            ?
_chemical_melting_point          445.45
_chemical_formula_moiety         'C14 H13 N2 O, Cl'
_chemical_formula_sum            'C14 H13 Cl N2 O'
_chemical_formula_weight         260.71

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   9.4142(15)
_cell_length_b                   7.1434(12)
_cell_length_c                   18.676(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.476(4)
_cell_angle_gamma                90.00
_cell_volume                     1238.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3342
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      22.58

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8979
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20463
_diffrn_reflns_av_R_equivalents  0.1520
_diffrn_reflns_av_sigmaI/netI    0.1117
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2683
_reflns_number_gt                1524
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0279P)²+1.0063P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2683
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1365
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl4 Cl 0.13669(8) 0.05152(11) 0.89339(4) 0.0298(2) Uani 1 1 d . . .
O11 O 1.0577(2) 0.6864(3) 0.94471(11) 0.0350(6) Uani 1 1 d . . .
H11O H 1.098(3) 0.808(5) 0.9301(18) 0.053 Uiso 1 1 d . . .
N4 N 0.9216(3) 0.6927(3) 0.90354(13) 0.0258(6) Uani 1 1 d . . .
N1 N 0.6631(2) 0.7453(3) 0.81848(13) 0.0188(6) Uani 1 1 d . . .
C3 C 0.9061(3) 0.6458(4) 0.83041(15) 0.0204(7) Uani 1 1 d . . .
C2 C 0.7776(3) 0.6732(4) 0.78911(16) 0.0183(7) Uani 1 1 d . . .
H2 H 0.7646 0.6428 0.7389 0.022 Uiso 1 1 calc R . .
C9 C 0.5243(3) 0.7869(4) 0.78816(17) 0.0198(7) Uani 1 1 d . . .
C12 C 0.4692(3) 0.7861(4) 0.71019(16) 0.0184(7) Uani 1 1 d . . .
C13 C 0.5533(3) 0.8439(4) 0.65955(16) 0.0210(7) Uani 1 1 d . . .
H13 H 0.6509 0.8785 0.6752 0.025 Uiso 1 1 calc R . .
C14 C 0.4959(3) 0.8512(4) 0.58683(17) 0.0253(7) Uani 1 1 d . . .
H14 H 0.5544 0.8901 0.5527 0.030 Uiso 1 1 calc R . .
C15 C 0.3536(3) 0.8023(4) 0.56313(18) 0.0270(8) Uani 1 1 d . . .
H15 H 0.3145 0.8084 0.5129 0.032 Uiso 1 1 calc R . .
C8 C 0.4533(3) 0.8409(4) 0.84513(17) 0.0243(7) Uani 1 1 d . . .
H8 H 0.3548 0.8760 0.8399 0.029 Uiso 1 1 calc R . .
C7 C 0.5467(3) 0.8355(4) 0.90941(17) 0.0256(8) Uani 1 1 d . . .
H7 H 0.5251 0.8670 0.9559 0.031 Uiso 1 1 calc R . .
C6 C 0.6798(3) 0.7753(4) 0.89425(16) 0.0219(7) Uani 1 1 d . . .
C5 C 0.8144(3) 0.7533(4) 0.93518(17) 0.0257(7) Uani 1 1 d . . .
H5 H 0.8301 0.7813 0.9856 0.031 Uiso 1 1 calc R . .
C17 C 0.3257(3) 0.7365(4) 0.68567(18) 0.0244(7) Uani 1 1 d . . .
H17 H 0.2668 0.6968 0.7195 0.029 Uiso 1 1 calc R . .
C16 C 0.2687(3) 0.7448(4) 0.61258(18) 0.0290(8) Uani 1 1 d . . .
H16 H 0.1711 0.7108 0.5964 0.035 Uiso 1 1 calc R . .
C10 C 1.0327(3) 0.5625(5) 0.80382(16) 0.0280(8) Uani 1 1 d . . .
H10A H 1.0080 0.5370 0.7517 0.042 Uiso 1 1 calc R . .
H10C H 1.0598 0.4454 0.8298 0.042 Uiso 1 1 calc R . .
H10B H 1.1137 0.6504 0.8124 0.042 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl4 0.0272(4) 0.0369(5) 0.0262(4) -0.0050(4) 0.0071(3) -0.0018(4)
O11 0.0299(14) 0.0417(15) 0.0292(14) 0.0031(11) -0.0077(11) -0.0038(11)
N4 0.0222(15) 0.0306(16) 0.0229(15) 0.0022(13) -0.0010(12) -0.0039(12)
N1 0.0225(14) 0.0145(13) 0.0205(14) -0.0011(11) 0.0069(11) 0.0009(11)
C3 0.0225(17) 0.0210(17) 0.0174(17) -0.0014(14) 0.0023(14) -0.0057(14)
C2 0.0205(17) 0.0144(16) 0.0208(17) -0.0031(13) 0.0054(14) -0.0013(13)
C9 0.0194(17) 0.0117(16) 0.030(2) 0.0023(14) 0.0098(15) -0.0001(13)
C12 0.0194(17) 0.0087(15) 0.0271(19) -0.0006(14) 0.0034(14) 0.0014(13)
C13 0.0181(16) 0.0178(16) 0.0267(19) 0.0006(14) 0.0026(14) 0.0005(13)
C14 0.0250(18) 0.0230(18) 0.028(2) 0.0011(15) 0.0055(15) 0.0010(14)
C15 0.0293(19) 0.0222(18) 0.0274(19) -0.0029(15) -0.0021(15) 0.0045(14)
C8 0.0256(17) 0.0148(16) 0.036(2) 0.0008(15) 0.0151(16) 0.0021(14)
C7 0.038(2) 0.0169(17) 0.026(2) -0.0018(15) 0.0179(17) -0.0007(15)
C6 0.033(2) 0.0139(16) 0.0207(18) -0.0008(14) 0.0103(16) -0.0016(14)
C5 0.038(2) 0.0215(17) 0.0182(17) -0.0007(14) 0.0050(16) -0.0054(15)
C17 0.0228(18) 0.0162(16) 0.037(2) -0.0016(15) 0.0118(15) -0.0013(14)
C16 0.0192(17) 0.0238(19) 0.043(2) -0.0068(17) 0.0013(16) -0.0012(15)
C10 0.0210(17) 0.037(2) 0.0264(18) 0.0022(16) 0.0040(14) 0.0034(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. 
;

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
O11 N4 1.382(3) . ?
O11 H11O 1.00(3) . ?
N4 C5 1.324(3) . ?
N4 C3 1.390(3) . ?
N1 C9 1.369(3) . ?
N1 C2 1.386(3) . ?
N1 C6 1.414(3) . ?
C3 C2 1.337(4) . ?
C3 C10 1.489(4) . ?
C2 H2 0.9500 . ?
C9 C8 1.400(4) . ?
C9 C12 1.463(4) . ?
C12 C13 1.392(4) . ?
C12 C17 1.400(4) . ?
C13 C14 1.377(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(4) . ?
C15 H15 0.9500 . ?
C8 C7 1.367(4) . ?
C8 H8 0.9500 . ?
C7 C6 1.398(4) . ?
C7 H7 0.9500 . ?
C6 C5 1.376(4) . ?
C5 H5 0.9500 . ?
C17 C16 1.383(4) . ?
C17 H17 0.9500 . ?
C16 H16 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10B 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
N4 O11 H11O 100.3(19) . . ?
C5 N4 O11 117.9(3) . . ?
C5 N4 C3 123.5(3) . . ?
O11 N4 C3 118.5(2) . . ?
C9 N1 C2 132.0(3) . . ?
C9 N1 C6 108.8(2) . . ?
C2 N1 C6 119.1(2) . . ?
C2 C3 N4 118.1(3) . . ?
C2 C3 C10 124.3(3) . . ?
N4 C3 C10 117.6(3) . . ?
C3 C2 N1 120.9(3) . . ?
C3 C2 H2 119.5 . . ?
N1 C2 H2 119.5 . . ?
N1 C9 C8 106.7(3) . . ?
N1 C9 C12 124.6(2) . . ?
C8 C9 C12 128.5(3) . . ?
C13 C12 C17 118.6(3) . . ?
C13 C12 C9 121.8(3) . . ?
C17 C12 C9 119.4(3) . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C7 C8 C9 110.0(3) . . ?
C7 C8 H8 125.0 . . ?
C9 C8 H8 125.0 . . ?
C8 C7 C6 107.4(3) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C5 C6 C7 134.2(3) . . ?
C5 C6 N1 118.6(3) . . ?
C7 C6 N1 107.1(3) . . ?
N4 C5 C6 119.3(3) . . ?
N4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C16 C17 C12 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10C C10 H10B 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
C5 N4 C3 C2 3.8(4) . . . . ?
O11 N4 C3 C2 -172.3(3) . . . . ?
C5 N4 C3 C10 -174.3(3) . . . . ?
O11 N4 C3 C10 9.6(4) . . . . ?
N4 C3 C2 N1 -0.3(4) . . . . ?
C10 C3 C2 N1 177.6(3) . . . . ?
C9 N1 C2 C3 179.3(3) . . . . ?
C6 N1 C2 C3 -5.3(4) . . . . ?
C2 N1 C9 C8 175.0(3) . . . . ?
C6 N1 C9 C8 -0.7(3) . . . . ?
C2 N1 C9 C12 -9.0(5) . . . . ?
C6 N1 C9 C12 175.2(2) . . . . ?
N1 C9 C12 C13 -36.0(4) . . . . ?
C8 C9 C12 C13 139.0(3) . . . . ?
N1 C9 C12 C17 147.7(3) . . . . ?
C8 C9 C12 C17 -37.2(4) . . . . ?
C17 C12 C13 C14 -0.2(4) . . . . ?
C9 C12 C13 C14 -176.5(3) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
N1 C9 C8 C7 0.9(3) . . . . ?
C12 C9 C8 C7 -174.9(3) . . . . ?
C9 C8 C7 C6 -0.7(3) . . . . ?
C8 C7 C6 C5 175.6(3) . . . . ?
C8 C7 C6 N1 0.2(3) . . . . ?
C9 N1 C6 C5 -175.9(3) . . . . ?
C2 N1 C6 C5 7.7(4) . . . . ?
C9 N1 C6 C7 0.3(3) . . . . ?
C2 N1 C6 C7 -176.0(2) . . . . ?
O11 N4 C5 C6 174.9(3) . . . . ?
C3 N4 C5 C6 -1.2(4) . . . . ?
C7 C6 C5 N4 -179.5(3) . . . . ?
N1 C6 C5 N4 -4.6(4) . . . . ?
C13 C12 C17 C16 0.0(4) . . . . ?
C9 C12 C17 C16 176.3(3) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C12 C17 C16 C15 0.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.072
_exptl_crystal_recrystallization_method 
'conversion to salt form in dichloromethane'
