# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_alpha-phase-ortho
_database_code_depnum_ccdc_archive 'CCDC 1955680'
loop_
_audit_author_name
_audit_author_address
'Christos Constantinides'
;University of Michigan Dearborn
United States of America
;
_audit_update_record             
;
2020-05-16 deposited with the CCDC.	2020-07-31 downloaded from the CCDC.
;
_audit_creation_date             2019-11-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 N4'
_chemical_formula_sum            'C18 H13 N4'
_chemical_formula_weight         285.32
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H13 N4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.1656(3)
_cell_length_b                   10.9705(4)
_cell_length_c                   17.5843(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1382.31(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2053
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      75.8390
_cell_measurement_theta_min      4.7030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             596
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 4 -9 0.0325
0 -4 9 0.0155
4 -1 -6 0.0909
-4 2 2 0.0891
0 -6 -5 0.0176
0 6 5 0.0176

_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.035
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0047 3.9935 -9.0219 0.6659 -0.3669 0.5997
-0.0047 -3.9935 9.0219 -0.6659 0.3669 -0.5997
4.3037 -1.0060 -5.9866 0.7797 -0.4519 -0.5826
-4.0017 2.0031 1.9808 -0.4496 0.3301 0.7340
0.0009 -6.0023 -4.9813 0.5388 0.6724 -0.4003
-0.0009 6.0023 4.9813 -0.5388 -0.6724 0.4003

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5012
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.490
_diffrn_reflns_theta_min         4.751
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3953
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  19.00   1.00    1.50    --  -42.15  57.00  90.00   82
  2  ω      1.00  34.00   1.00    1.50    --   42.15 -99.00   0.00   33
  3  ω     30.00  88.00   1.00    1.50    --   42.15-125.00 -90.00   58
  4  ω     54.00  80.00   1.00    6.00    --  112.00-111.00 150.00   26
  5  ω    130.00 178.00   1.00    6.00    --  112.00 111.00   0.00   48
  6  ω    100.00 144.00   1.00    6.00    --  112.00 111.00-120.00   44
  7  ω     85.00 120.00   1.00    6.00    --  112.00  30.00-150.00   35
  8  ω    101.00 155.00   1.00    6.00    --  112.00 111.00 -90.00   54
  9  ω    141.00 167.00   1.00    6.00    --  112.00  30.00-150.00   26
 10  ω     37.00  62.00   1.00    6.00    --  112.00-111.00 -60.00   25
 11  ω    132.00 165.00   1.00    6.00    --  112.00  30.00 150.00   33
 12  ω     86.00 178.00   1.00    6.00    --  112.00  45.00  30.00   92
 13  ω    116.00 164.00   1.00    6.00    --  112.00 111.00-150.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0608074000
_diffrn_orient_matrix_UB_12      -0.0208612000
_diffrn_orient_matrix_UB_13      -0.0830139000
_diffrn_orient_matrix_UB_21      -0.1390887000
_diffrn_orient_matrix_UB_22      -0.1065810000
_diffrn_orient_matrix_UB_23      -0.0065865000
_diffrn_orient_matrix_UB_31      -0.1522149000
_diffrn_orient_matrix_UB_32      0.0891490000
_diffrn_orient_matrix_UB_33      -0.0270889000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.629
_reflns_Friedel_fraction_full    0.888
_reflns_Friedel_fraction_max     0.874
_reflns_number_gt                2374
_reflns_number_total             2674
_reflns_odcompleteness_completeness 99.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.49
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 846 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2674
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0559P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1001
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.4709(3) 0.66496(16) 0.50105(10) 0.0196(4) Uani 1 1 d . . . . .
N2 N 0.5209(2) 0.67470(17) 0.42634(10) 0.0191(4) Uani 1 1 d . . . . .
N3 N 0.4966(3) 0.45739(17) 0.41288(10) 0.0216(4) Uani 1 1 d . . . . .
N4 N 0.5478(3) 0.76790(19) 0.61301(11) 0.0257(4) Uani 1 1 d . . . . .
C1 C 0.5309(3) 0.5704(2) 0.38740(12) 0.0189(4) Uani 1 1 d . . . . .
C2 C 0.4266(3) 0.4513(2) 0.48556(12) 0.0200(4) Uani 1 1 d . . . . .
C3 C 0.4086(3) 0.5551(2) 0.53228(12) 0.0184(4) Uani 1 1 d . . . . .
C4 C 0.3216(3) 0.5467(2) 0.60363(12) 0.0221(4) Uani 1 1 d . . . . .
H4 H 0.3082 0.6155 0.6340 0.027 Uiso 1 1 calc R . . . .
C5 C 0.2560(3) 0.4348(2) 0.62828(12) 0.0251(5) Uani 1 1 d . . . . .
H5 H 0.1971 0.4291 0.6753 0.030 Uiso 1 1 calc R . . . .
C6 C 0.2769(3) 0.3303(2) 0.58353(14) 0.0261(5) Uani 1 1 d . . . . .
H6 H 0.2340 0.2555 0.6012 0.031 Uiso 1 1 calc R . . . .
C7 C 0.3617(3) 0.3384(2) 0.51287(13) 0.0243(4) Uani 1 1 d . . . . .
H7 H 0.3757 0.2687 0.4833 0.029 Uiso 1 1 calc R . . . .
C8 C 0.5949(3) 0.5833(2) 0.30744(12) 0.0196(4) Uani 1 1 d . . . . .
C9 C 0.6599(3) 0.4816(2) 0.26768(13) 0.0224(4) Uani 1 1 d . . . . .
H9 H 0.6538 0.4050 0.2902 0.027 Uiso 1 1 calc R . . . .
C10 C 0.7334(3) 0.4933(2) 0.19509(13) 0.0251(5) Uani 1 1 d . . . . .
H10 H 0.7791 0.4253 0.1696 0.030 Uiso 1 1 calc R . . . .
C11 C 0.7384(3) 0.6075(2) 0.16053(12) 0.0265(5) Uani 1 1 d . . . . .
H11 H 0.7886 0.6158 0.1120 0.032 Uiso 1 1 calc R . . . .
C12 C 0.6685(3) 0.7092(2) 0.19843(13) 0.0248(5) Uani 1 1 d . . . . .
H12 H 0.6695 0.7850 0.1747 0.030 Uiso 1 1 calc R . . . .
C13 C 0.5971(3) 0.6979(2) 0.27174(13) 0.0220(4) Uani 1 1 d . . . . .
H13 H 0.5509 0.7660 0.2970 0.026 Uiso 1 1 calc R . . . .
C14 C 0.4865(3) 0.77690(19) 0.54185(12) 0.0204(4) Uani 1 1 d . . . . .
C15 C 0.4450(3) 0.8860(2) 0.50525(14) 0.0248(5) Uani 1 1 d . . . . .
H15 H 0.4034 0.8873 0.4552 0.030 Uiso 1 1 calc R . . . .
C16 C 0.4683(3) 0.9927(2) 0.54654(16) 0.0303(5) Uani 1 1 d . . . . .
H16 H 0.4420 1.0679 0.5245 0.036 Uiso 1 1 calc R . . . .
C17 C 0.5311(4) 0.9861(2) 0.62084(16) 0.0328(6) Uani 1 1 d . . . . .
H17 H 0.5487 1.0566 0.6493 0.039 Uiso 1 1 calc R . . . .
C18 C 0.5674(4) 0.8724(3) 0.65202(14) 0.0312(5) Uani 1 1 d . . . . .
H18 H 0.6072 0.8683 0.7023 0.037 Uiso 1 1 calc R . . . .


_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
N1 N2 1.366(2) . ?
N1 C3 1.397(3) . ?
N1 C14 1.427(3) . ?
N2 C1 1.335(3) . ?
N3 C1 1.341(3) . ?
N3 C2 1.375(3) . ?
N4 C14 1.330(3) . ?
N4 C18 1.344(3) . ?
C1 C8 1.486(3) . ?
C2 C3 1.410(3) . ?
C2 C7 1.408(3) . ?
C3 C4 1.404(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.396(3) . ?
C8 C13 1.405(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.394(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.393(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(4) . ?
C18 H18 0.9300 . ?

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
N2 N1 C3 121.96(18) . . ?
N2 N1 C14 113.31(17) . . ?
C3 N1 C14 124.72(17) . . ?
C1 N2 N1 116.12(17) . . ?
C1 N3 C2 114.98(18) . . ?
C14 N4 C18 116.9(2) . . ?
N2 C1 N3 127.66(18) . . ?
N2 C1 C8 114.85(19) . . ?
N3 C1 C8 117.44(19) . . ?
N3 C2 C3 122.4(2) . . ?
N3 C2 C7 118.7(2) . . ?
C7 C2 C3 118.8(2) . . ?
N1 C3 C2 116.00(18) . . ?
N1 C3 C4 123.4(2) . . ?
C4 C3 C2 120.5(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.3(2) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.9(2) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6 120.0 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C1 120.0(2) . . ?
C9 C8 C13 119.2(2) . . ?
C13 C8 C1 120.8(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 120.1 . . ?
C12 C13 C8 119.8(2) . . ?
C12 C13 H13 120.1 . . ?
N4 C14 N1 115.80(19) . . ?
N4 C14 C15 124.7(2) . . ?
C15 C14 N1 119.41(19) . . ?
C14 C15 H15 121.4 . . ?
C16 C15 C14 117.3(2) . . ?
C16 C15 H15 121.4 . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.2(2) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.8(2) . . ?
C18 C17 H17 120.6 . . ?
N4 C18 C17 123.1(2) . . ?
N4 C18 H18 118.5 . . ?
C17 C18 H18 118.5 . . ?


_ins_header                      
;
TITL alpha-phase-ortho in P2(1)2(1)2(1) 
REM P2(1)2(1)2(1) (#19 in standard setting)
CELL 1.54184   7.165591  10.970526  17.584296  90.0000  90.0000  90.0000
ZERR    4.00   0.000252   0.000444   0.000636   0.0000   0.0000   0.0000
LATT -1
SYMM -x+1/2,-y, z+1/2 
SYMM -x, y+1/2,-z+1/2 
SYMM  x+1/2,-y+1/2,-z 
SFAC C H N
UNIT 72.00 52.00 16.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.369
_oxdiff_exptl_absorpt_empirical_full_min 0.768
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_beta-mp-red
_database_code_depnum_ccdc_archive 'CCDC 1955684'
loop_
_audit_author_name
_audit_author_address
'Christos Constantinides'
;University of Michigan Dearborn
United States of America
;
_audit_update_record             
;
2020-05-16 deposited with the CCDC.	2020-07-31 downloaded from the CCDC.
;
_audit_creation_date             2019-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 N4'
_chemical_formula_sum            'C18 H13 N4'
_chemical_formula_weight         285.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H13 N4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   19.7893(9)
_cell_length_b                   3.76820(10)
_cell_length_c                   19.7322(8)
_cell_angle_alpha                90
_cell_angle_beta                 114.594(5)
_cell_angle_gamma                90
_cell_volume                     1337.94(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3967
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.4570
_cell_measurement_theta_min      4.8530
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             596
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 0 -13 0.0378
-4 0 13 0.0468
-2 -2 0 0.1010
2 2 0 0.0810
12 0 -1 0.0132
-12 0 1 0.0132

_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.026
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.0376 -0.0023 -13.0000 0.1668 -0.9496 0.3392
-4.0376 0.0023 13.0000 -0.1668 0.9496 -0.3392
-1.9375 -2.0041 -0.0058 -0.0894 0.2462 0.7938
1.9375 2.0041 0.0058 0.0894 -0.2462 -0.7938
11.9896 0.0230 -0.9618 0.9697 0.1580 -0.1578
-11.9896 -0.0230 0.9618 -0.9697 -0.1580 0.1578

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.649
_diffrn_reflns_theta_min         4.500
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  70.00   1.00   11.00    --   41.65 -57.00  30.00  100
  2  ω    -30.00  70.00   1.00   11.00    --   41.65 -57.00 -90.00  100
  3  ω    -34.00  74.00   1.00   11.00    --   41.65 -77.00-180.00  108
  4  ω     36.00 145.00   1.00   37.00    --  112.00 -77.00 -60.00  109
  5  ω     40.00 141.00   1.00   37.00    --  112.00 -61.00 150.00  101
  6  ω     83.00 178.00   1.00   37.00    --  112.00  61.00 -90.00   95
  7  ω     39.00 138.00   1.00   37.00    --  112.00 -45.00 -60.00   99
  8  ω     36.00 116.00   1.00   37.00    --  112.00-111.00-150.00   80
  9  ω     29.00 109.00   1.00   37.00    --  112.00 -94.00-120.00   80
 10  ω     39.00 138.00   1.00   37.00    --  112.00 -45.00  30.00   99
 11  ω     84.00 128.00   1.00   37.00    --  112.00  61.00 -60.00   44
 12  ω     37.00 111.00   1.00   37.00    --  112.00-111.00   0.00   74
 13  ω     56.00 106.00   1.00   37.00    --  112.00-111.00 150.00   50
 14  ω     24.00 175.00   1.00   37.00    --  112.00   0.00  90.00  151
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0819609000
_diffrn_orient_matrix_UB_12      -0.0346624000
_diffrn_orient_matrix_UB_13      0.0126320000
_diffrn_orient_matrix_UB_21      0.0198093000
_diffrn_orient_matrix_UB_22      -0.1422065000
_diffrn_orient_matrix_UB_23      0.0792253000
_diffrn_orient_matrix_UB_31      -0.0148877000
_diffrn_orient_matrix_UB_32      -0.3816038000
_diffrn_orient_matrix_UB_33      -0.0306493000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2376
_reflns_number_total             2797
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2797
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0694P)²+0.3285P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1196
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N1 N 0.21479(6) 0.4215(3) 0.36744(5) 0.0225(2) Uani 1 1 d . . . . .
N2 N 0.28229(6) 0.5239(3) 0.42100(6) 0.0230(2) Uani 1 1 d . . . . .
N3 N 0.22456(6) 0.6711(3) 0.50256(6) 0.0249(3) Uani 1 1 d . . . . .
N4 N 0.15935(6) 0.4161(3) 0.23703(6) 0.0244(2) Uani 1 1 d . . . . .
C1 C 0.28260(7) 0.6422(3) 0.48498(6) 0.0219(3) Uani 1 1 d . . . . .
C2 C 0.15838(7) 0.5474(3) 0.45031(7) 0.0237(3) Uani 1 1 d . . . . .
C3 C 0.15071(7) 0.4105(3) 0.38050(7) 0.0227(3) Uani 1 1 d . . . . .
C4 C 0.08300(7) 0.2654(4) 0.33094(7) 0.0253(3) Uani 1 1 d . . . . .
H4 H 0.0787 0.1658 0.2862 0.030 Uiso 1 1 calc R . . . .
C5 C 0.02243(8) 0.2714(4) 0.34906(7) 0.0281(3) Uani 1 1 d . . . . .
H5 H -0.0228 0.1774 0.3161 0.034 Uiso 1 1 calc R . . . .
C6 C 0.02884(8) 0.4182(4) 0.41680(7) 0.0296(3) Uani 1 1 d . . . . .
H6 H -0.0124 0.4257 0.4280 0.036 Uiso 1 1 calc R . . . .
C7 C 0.09556(8) 0.5506(4) 0.46658(7) 0.0276(3) Uani 1 1 d . . . . .
H7 H 0.0994 0.6437 0.5117 0.033 Uiso 1 1 calc R . . . .
C8 C 0.35620(7) 0.7592(3) 0.54135(6) 0.0233(3) Uani 1 1 d . . . . .
C9 C 0.36181(8) 0.8977(3) 0.60936(7) 0.0255(3) Uani 1 1 d . . . . .
H9 H 0.3197 0.9144 0.6188 0.031 Uiso 1 1 calc R . . . .
C10 C 0.42989(8) 1.0098(4) 0.66253(7) 0.0286(3) Uani 1 1 d . . . . .
H10 H 0.4332 1.1009 0.7076 0.034 Uiso 1 1 calc R . . . .
C11 C 0.49305(8) 0.9870(4) 0.64898(7) 0.0297(3) Uani 1 1 d . . . . .
H11 H 0.5386 1.0638 0.6847 0.036 Uiso 1 1 calc R . . . .
C12 C 0.48795(8) 0.8487(4) 0.58167(8) 0.0303(3) Uani 1 1 d . . . . .
H12 H 0.5303 0.8319 0.5725 0.036 Uiso 1 1 calc R . . . .
C13 C 0.41989(8) 0.7356(4) 0.52817(7) 0.0267(3) Uani 1 1 d . . . . .
H13 H 0.4168 0.6436 0.4833 0.032 Uiso 1 1 calc R . . . .
C14 C 0.21798(7) 0.3292(3) 0.29872(6) 0.0219(3) Uani 1 1 d . . . . .
C15 C 0.28177(7) 0.1660(4) 0.30028(7) 0.0254(3) Uani 1 1 d . . . . .
H15 H 0.3215 0.1095 0.3450 0.031 Uiso 1 1 calc R . . . .
C16 C 0.28361(8) 0.0912(4) 0.23223(7) 0.0282(3) Uani 1 1 d . . . . .
H16 H 0.3252 -0.0167 0.2306 0.034 Uiso 1 1 calc R . . . .
C17 C 0.22324(8) 0.1781(4) 0.16677(7) 0.0283(3) Uani 1 1 d . . . . .
H17 H 0.2234 0.1301 0.1206 0.034 Uiso 1 1 calc R . . . .
C18 C 0.16288(8) 0.3380(4) 0.17207(7) 0.0273(3) Uani 1 1 d . . . . .
H18 H 0.1222 0.3952 0.1281 0.033 Uiso 1 1 calc R . . . .


_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
N1 N2 1.3693(15) . ?
N1 C3 1.3958(16) . ?
N1 C14 1.4265(14) . ?
N2 C1 1.3366(15) . ?
N3 C1 1.3351(17) . ?
N3 C2 1.3680(17) . ?
N4 C14 1.3265(17) . ?
N4 C18 1.3450(15) . ?
C1 C8 1.4847(18) . ?
C2 C3 1.4187(17) . ?
C2 C7 1.4074(18) . ?
C3 C4 1.4000(19) . ?
C4 C5 1.3863(18) . ?
C5 C6 1.4026(19) . ?
C6 C7 1.370(2) . ?
C8 C9 1.4006(16) . ?
C8 C13 1.3916(18) . ?
C9 C10 1.385(2) . ?
C10 C11 1.385(2) . ?
C11 C12 1.3907(19) . ?
C12 C13 1.388(2) . ?
C14 C15 1.3930(18) . ?
C15 C16 1.3871(17) . ?
C16 C17 1.385(2) . ?
C17 C18 1.380(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
N2 N1 C3 122.36(10) . . ?
N2 N1 C14 112.80(10) . . ?
C3 N1 C14 124.84(11) . . ?
C1 N2 N1 116.27(10) . . ?
C1 N3 C2 115.71(10) . . ?
C14 N4 C18 116.62(12) . . ?
N2 C1 C8 115.09(11) . . ?
N3 C1 N2 127.32(12) . . ?
N3 C1 C8 117.58(10) . . ?
N3 C2 C3 122.52(12) . . ?
N3 C2 C7 119.00(11) . . ?
C7 C2 C3 118.48(12) . . ?
N1 C3 C2 115.48(12) . . ?
N1 C3 C4 124.16(11) . . ?
C4 C3 C2 120.32(12) . . ?
C5 C4 C3 119.50(12) . . ?
C4 C5 C6 120.48(13) . . ?
C7 C6 C5 120.31(12) . . ?
C6 C7 C2 120.83(12) . . ?
C9 C8 C1 119.36(12) . . ?
C13 C8 C1 121.57(11) . . ?
C13 C8 C9 119.07(12) . . ?
C10 C9 C8 120.25(12) . . ?
C9 C10 C11 120.41(12) . . ?
C10 C11 C12 119.66(13) . . ?
C13 C12 C11 120.21(13) . . ?
C12 C13 C8 120.39(12) . . ?
N4 C14 N1 116.38(11) . . ?
N4 C14 C15 124.59(11) . . ?
C15 C14 N1 119.00(11) . . ?
C16 C15 C14 117.18(12) . . ?
C17 C16 C15 119.66(12) . . ?
C18 C17 C16 118.06(11) . . ?
N4 C18 C17 123.89(12) . . ?


_ins_header                      
;
TITL beta-mP-red in P2(1)/c 
REM P2(1)/c (#14 in standard setting)
CELL 1.54184  19.789302   3.768244  19.732166  90.0000 114.5942  90.0000
ZERR    3.00   0.000933   0.000117   0.000805   0.0000   0.0054   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2 
SFAC C H N
UNIT 54.00 39.00 12.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.394
_oxdiff_exptl_absorpt_empirical_full_min 0.819
_exptl_crystal_preparation       'Magnetic properties'
