# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_814
_database_code_depnum_ccdc_archive 'CCDC 1813403'
_audit_update_record             
;
2017-12-24 deposited with the CCDC.
2018-03-09 downloaded from the CCDC.
;
_audit_creation_date             2017-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H19 N O'
_chemical_formula_sum            'C24 H19 N O'
_chemical_formula_weight         337.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4619(4)
_cell_length_b                   9.7534(4)
_cell_length_c                   10.5387(5)
_cell_angle_alpha                68.185(4)
_cell_angle_beta                 78.205(4)
_cell_angle_gamma                88.782(4)
_cell_volume                     882.26(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5656
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6050
_cell_measurement_theta_min      4.6150
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8621
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.775
_diffrn_reflns_theta_min         4.624
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     38.00  87.00   0.50    0.50    --    0.00  57.00 120.00   98
  2  ω     38.00  89.00   0.50    0.50    --    0.00  38.00 -60.00  102
  3  ω    -19.00  25.00   0.50    0.50    --    0.00 -77.00-180.00   88
  4  ω     47.00  73.00   0.50    0.50    --    0.00  38.00   0.00   52
  5  ω    -15.00  33.00   0.50    0.50    --    0.00  38.00 -60.00   96
  6  ω    -48.00 -21.00   0.50    0.50    --    0.00 -77.00-180.00   54
  7  ω    -11.00  14.00   0.50    0.50    --    0.00  38.00   0.00   50
  8  ω     40.00  81.00   0.50    0.50    --   95.20 -61.00 -30.00   82
  9  ω     43.00 112.00   0.50    0.50    --   95.20 -30.00 -60.00  138
 10  ω     66.00 133.00   0.50    0.50    --   95.20  77.00 -90.00  134
 11  ω     56.00 111.00   0.50    0.50    --   95.20 -30.00  30.00  110
 12  ω      7.00 119.00   0.50    0.50    --   95.20 -82.00 -30.00  224
 13  ω     74.00 101.00   0.50    0.50    --   95.20 -82.00 120.00   54
 14  ω     92.00 118.00   0.50    0.50    --   95.20 -77.00  90.00   52
 15  ω      9.00  48.00   0.50    0.50    --   95.20 -30.00  30.00   78
 16  ω     50.00 116.00   0.50    0.50    --   95.20 -82.00  60.00  132
 17  ω      8.00  34.00   0.50    0.50    --   95.20 -30.00 -60.00   52
 18  ω      7.00 114.00   0.50    0.50    --   95.20 -15.00   0.00  214
 19  ω     68.00 105.00   0.50    0.50    --   95.20 -82.00 -90.00   74
 20  ω     13.00  52.00   0.50    0.50    --   95.20 -82.00 -90.00   78
 21  ω     29.00  55.00   0.50    0.50    --   95.20 -82.00-120.00   52
 22  ω     62.00 105.00   0.50    0.50    --   95.20 -82.00-120.00   86
 23  ω    110.00 183.00   0.50    0.50    --   95.20  45.00 -30.00  146
 24  ω     94.00 125.00   0.50    0.50    --   95.20 -82.00   0.00   62
 25  ω      7.00 109.00   0.50    0.50    --   95.20 -45.00 150.00  204
 26  ω    160.00 185.00   0.50    0.50    --   95.20  77.00 -90.00   50
 27  ω     89.00 117.00   0.50    0.50    --   95.20 -82.00 145.13   56
 28  ω     31.00  62.00   0.50    0.50    --   95.20 -82.00 145.13   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1414242000
_diffrn_orient_matrix_UB_12      0.0970131000
_diffrn_orient_matrix_UB_13      -0.0445146000
_diffrn_orient_matrix_UB_21      0.0737121000
_diffrn_orient_matrix_UB_22      -0.1318700000
_diffrn_orient_matrix_UB_23      0.0905699000
_diffrn_orient_matrix_UB_31      0.0482859000
_diffrn_orient_matrix_UB_32      -0.0474319000
_diffrn_orient_matrix_UB_33      -0.1255859000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3169
_reflns_number_total             3439
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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         0.232
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3439
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.031
_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)+(0.0624P)²+0.2352P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1132
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C8(H8), C12(H12), C18(H18), C9(H9), C20(H20), C24(H24),
 C14(H14), C11(H11), C23(H23), C15(H15), C21(H21), C17(H17), C16(H16), C22(H22)
2.b Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c)
;
_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
O1 O 0.68355(10) 0.21500(11) 0.28263(9) 0.0346(2) Uani 1 1 d . . . . .
N1 N 0.54491(10) 0.22614(10) 0.48435(10) 0.0236(2) Uani 1 1 d . . . . .
C7 C 0.66375(12) 0.17315(13) 0.55395(12) 0.0240(3) Uani 1 1 d . . . . .
C4 C 0.33490(13) 0.36342(12) 0.33618(12) 0.0251(3) Uani 1 1 d . . . . .
C13 C 0.39425(12) 0.22753(13) 0.70698(12) 0.0246(3) Uani 1 1 d . . . . .
C2 C 0.41795(12) 0.26293(12) 0.55374(12) 0.0236(2) Uani 1 1 d . . . . .
C5 C 0.45765(13) 0.32169(13) 0.27018(12) 0.0260(3) Uani 1 1 d . . . . .
H5 H 0.468970 0.339664 0.175497 0.031 Uiso 1 1 calc R . . . .
C3 C 0.31479(13) 0.32983(12) 0.48234(12) 0.0252(3) Uani 1 1 d . . . . .
H3 H 0.229946 0.353928 0.529789 0.030 Uiso 1 1 calc R . . . .
C19 C 0.22417(13) 0.44199(13) 0.25889(12) 0.0262(3) Uani 1 1 d . . . . .
C6 C 0.57023(13) 0.25131(13) 0.33992(12) 0.0259(3) Uani 1 1 d . . . . .
C8 C 0.72560(13) 0.26045(13) 0.60822(12) 0.0268(3) Uani 1 1 d . . . . .
H8 H 0.690808 0.352506 0.600416 0.032 Uiso 1 1 calc R . . . .
C12 C 0.71789(13) 0.03773(13) 0.56255(13) 0.0278(3) Uani 1 1 d . . . . .
H12 H 0.677057 -0.020570 0.525235 0.033 Uiso 1 1 calc R . . . .
C18 C 0.37810(13) 0.34278(14) 0.75500(13) 0.0297(3) Uani 1 1 d . . . . .
H18 H 0.387058 0.440146 0.691478 0.036 Uiso 1 1 calc R . . . .
C9 C 0.83982(13) 0.20995(14) 0.67438(13) 0.0300(3) Uani 1 1 d . . . . .
H9 H 0.879785 0.268201 0.712283 0.036 Uiso 1 1 calc R . . . .
C10 C 0.89566(13) 0.07407(14) 0.68508(13) 0.0304(3) Uani 1 1 d . . . . .
C20 C 0.07687(14) 0.41070(14) 0.31810(13) 0.0316(3) Uani 1 1 d . . . . .
H20 H 0.047180 0.340656 0.408252 0.038 Uiso 1 1 calc R . . . .
C24 C 0.26640(14) 0.55000(14) 0.12426(12) 0.0291(3) Uani 1 1 d . . . . .
H24 H 0.364215 0.572555 0.083646 0.035 Uiso 1 1 calc R . . . .
C14 C 0.37927(14) 0.08148(14) 0.80262(13) 0.0301(3) Uani 1 1 d . . . . .
H14 H 0.390482 0.003630 0.771332 0.036 Uiso 1 1 calc R . . . .
C11 C 0.83323(14) -0.01038(14) 0.62706(13) 0.0311(3) Uani 1 1 d . . . . .
H11 H 0.869843 -0.100996 0.631786 0.037 Uiso 1 1 calc R . . . .
C23 C 0.16375(15) 0.62374(15) 0.05078(13) 0.0344(3) Uani 1 1 d . . . . .
H23 H 0.192730 0.695516 -0.038588 0.041 Uiso 1 1 calc R . . . .
C15 C 0.34755(15) 0.05357(17) 0.94452(14) 0.0382(3) Uani 1 1 d . . . . .
H15 H 0.335555 -0.043636 1.008564 0.046 Uiso 1 1 calc R . . . .
C21 C -0.02565(15) 0.48297(16) 0.24391(15) 0.0370(3) Uani 1 1 d . . . . .
H21 H -0.123600 0.459527 0.283363 0.044 Uiso 1 1 calc R . . . .
C17 C 0.34862(14) 0.31317(17) 0.89756(14) 0.0368(3) Uani 1 1 d . . . . .
H17 H 0.339064 0.390691 0.929328 0.044 Uiso 1 1 calc R . . . .
C16 C 0.33351(15) 0.16882(18) 0.99208(14) 0.0401(3) Uani 1 1 d . . . . .
H16 H 0.313935 0.148947 1.087568 0.048 Uiso 1 1 calc R . . . .
C22 C 0.01783(15) 0.59019(16) 0.11091(14) 0.0369(3) Uani 1 1 d . . . . .
H22 H -0.051075 0.639788 0.061848 0.044 Uiso 1 1 calc R . . . .
C25 C 1.01771(16) 0.01828(18) 0.75891(16) 0.0431(4) Uani 1 1 d . . . . .
H25A H 1.073667 0.100664 0.756191 0.065 Uiso 1 1 calc GR . . . .
H25B H 1.078341 -0.037234 0.713238 0.065 Uiso 1 1 calc GR . . . .
H25C H 0.979031 -0.044200 0.854429 0.065 Uiso 1 1 calc GR . . . .


_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
O1 C6 1.2320(14) . ?
N1 C7 1.4491(14) . ?
N1 C2 1.3872(15) . ?
N1 C6 1.4178(15) . ?
C7 C8 1.3837(17) . ?
C7 C12 1.3843(16) . ?
C4 C5 1.3633(17) . ?
C4 C3 1.4227(16) . ?
C4 C19 1.4829(16) . ?
C13 C2 1.4894(16) . ?
C13 C18 1.3881(17) . ?
C13 C14 1.3957(17) . ?
C2 C3 1.3613(16) . ?
C5 H5 0.9300 . ?
C5 C6 1.4354(16) . ?
C3 H3 0.9300 . ?
C19 C20 1.3950(18) . ?
C19 C24 1.3992(17) . ?
C8 H8 0.9300 . ?
C8 C9 1.3882(17) . ?
C12 H12 0.9300 . ?
C12 C11 1.3849(17) . ?
C18 H18 0.9300 . ?
C18 C17 1.3885(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.3899(18) . ?
C10 C11 1.3942(19) . ?
C10 C25 1.5036(18) . ?
C20 H20 0.9300 . ?
C20 C21 1.3859(18) . ?
C24 H24 0.9300 . ?
C24 C23 1.3871(17) . ?
C14 H14 0.9300 . ?
C14 C15 1.3849(18) . ?
C11 H11 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.386(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.386(2) . ?
C17 H17 0.9300 . ?
C17 C16 1.379(2) . ?
C16 H16 0.9300 . ?
C22 H22 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
C2 N1 C7 120.92(9) . . ?
C2 N1 C6 122.06(10) . . ?
C6 N1 C7 116.77(9) . . ?
C8 C7 N1 119.68(10) . . ?
C8 C7 C12 120.13(11) . . ?
C12 C7 N1 120.17(10) . . ?
C5 C4 C3 118.35(11) . . ?
C5 C4 C19 121.41(10) . . ?
C3 C4 C19 120.24(11) . . ?
C18 C13 C2 118.77(10) . . ?
C18 C13 C14 119.75(11) . . ?
C14 C13 C2 121.36(11) . . ?
N1 C2 C13 119.74(10) . . ?
C3 C2 N1 120.14(10) . . ?
C3 C2 C13 120.11(10) . . ?
C4 C5 H5 118.5 . . ?
C4 C5 C6 123.10(11) . . ?
C6 C5 H5 118.5 . . ?
C4 C3 H3 119.5 . . ?
C2 C3 C4 120.95(11) . . ?
C2 C3 H3 119.5 . . ?
C20 C19 C4 121.17(11) . . ?
C20 C19 C24 118.70(11) . . ?
C24 C19 C4 120.14(11) . . ?
O1 C6 N1 120.06(11) . . ?
O1 C6 C5 124.62(11) . . ?
N1 C6 C5 115.31(10) . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.68(11) . . ?
C9 C8 H8 120.2 . . ?
C7 C12 H12 120.2 . . ?
C7 C12 C11 119.59(11) . . ?
C11 C12 H12 120.2 . . ?
C13 C18 H18 119.9 . . ?
C13 C18 C17 120.22(12) . . ?
C17 C18 H18 119.9 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.31(12) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C11 117.84(12) . . ?
C9 C10 C25 121.28(12) . . ?
C11 C10 C25 120.88(12) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.65(12) . . ?
C21 C20 H20 119.7 . . ?
C19 C24 H24 119.7 . . ?
C23 C24 C19 120.62(12) . . ?
C23 C24 H24 119.7 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.40(12) . . ?
C15 C14 H14 120.3 . . ?
C12 C11 C10 121.43(11) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C24 C23 H23 120.1 . . ?
C22 C23 C24 119.84(12) . . ?
C22 C23 H23 120.1 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.71(13) . . ?
C16 C15 H15 119.6 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 119.98(12) . . ?
C22 C21 H21 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 120.04(13) . . ?
C16 C17 H17 120.0 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.88(12) . . ?
C17 C16 H16 120.1 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.19(12) . . ?
C21 C22 H22 119.9 . . ?
C10 C25 H25A 109.5 . . ?
C10 C25 H25B 109.5 . . ?
C10 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_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 2.388
_oxdiff_exptl_absorpt_empirical_full_min 0.679
####################################################################### 
# 
# 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_20170115_pym_zhy_308
_database_code_depnum_ccdc_archive 'CCDC 1813854'
_audit_update_record             
;
2017-12-26 deposited with the CCDC.
2018-03-09 downloaded from the CCDC.
;
_audit_creation_date             2017-12-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H Cl3, C24 H18 N2'
_chemical_formula_sum            'C25 H19 Cl3 N2'
_chemical_formula_weight         453.77
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 '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                   10.6279(10)
_cell_length_b                   15.8991(10)
_cell_length_c                   13.4801(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.330(9)
_cell_angle_gamma                90
_cell_volume                     2240.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2691
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4420
_cell_measurement_theta_min      3.8800
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.846
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13092
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.873
_diffrn_reflns_theta_min         3.329
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -95.00 -34.00   1.00    5.00    --  -18.94 178.00 120.00   61
  2  ω    -49.00  40.00   1.00    5.00    --   19.33 -57.00 -60.00   89
  3  ω    -54.00  63.00   1.00    5.00    --   19.33 -19.00   0.00  117
  4  ω    -11.00  14.00   1.00    5.00    --   19.33  77.00  30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0387135000
_diffrn_orient_matrix_UB_12      -0.0203050000
_diffrn_orient_matrix_UB_13      -0.0304979000
_diffrn_orient_matrix_UB_21      -0.0530842000
_diffrn_orient_matrix_UB_22      -0.0245186000
_diffrn_orient_matrix_UB_23      -0.0227303000
_diffrn_orient_matrix_UB_31      -0.0165368000
_diffrn_orient_matrix_UB_32      0.0312708000
_diffrn_orient_matrix_UB_33      -0.0376755000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3322
_reflns_number_total             5112
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.762
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0840
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1311P)²+0.8741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2101
_refine_ls_wR_factor_ref         0.2443
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.063) H2(0.076) H3(0.078) H4(0.07) H8(0.05) H10(0.049)
 H13(0.059) H14(0.071) H15(0.088) H16(0.091) H17(0.066) H19(0.062) H20(0.074)
 H22A(0.145) H22B(0.145) H22C(0.145) H23(0.066) H24(0.057) H25(0.074)
 Fixed X: H1(0.565701) H2(0.428301) H3(0.243) H4(0.1875) H8(0.4235)
 H10(0.7421) H13(0.5898) H14(0.7245) H15(0.9228) H16(0.9889) H17(0.8556)
 H19(0.5591) H20(0.624301) H22A(0.852) H22B(0.7414) H22C(0.7185) H23(0.796399)
 H24(0.7301) H25(0.8576)
 Fixed Y: H1(0.4416) H2(0.406799) H3(0.333301) H4(0.2922) H8(0.324)
 H10(0.4503) H13(0.5771) H14(0.653501) H15(0.6005) H16(0.474699) H17(0.3966)
 H19(0.2651) H20(0.258901) H22A(0.3555) H22B(0.416499) H22C(0.3191) H23(0.481)
 H24(0.4887) H25(0.702)
 Fixed Z: H1(0.8801) H2(0.988) H3(0.9316) H4(0.7657) H8(0.4451) H10(0.5595)
 H13(0.7493) H14(0.8694) H15(0.9388) H16(0.8846) H17(0.763201) H19(0.3449)
 H20(0.192101) H22A(0.111101) H22B(0.064301) H22C(0.061201) H23(0.2448)
 H24(0.3971) H25(0.488)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.89778(14) 0.61359(9) 0.61775(12) 0.1098(5) Uani 1 1 d . . . . .
Cl2 Cl 0.99760(14) 0.61629(13) 0.43532(11) 0.1341(7) Uani 1 1 d . . . . .
Cl3 Cl 1.04016(12) 0.75492(8) 0.57457(12) 0.1038(5) Uani 1 1 d . . . . .
N1 N 0.5156(2) 0.39721(13) 0.67245(17) 0.0373(5) Uani 1 1 d . . . . .
N2 N 0.3338(2) 0.32310(15) 0.62017(19) 0.0471(6) Uani 1 1 d . . . . .
C1 C 0.4904(3) 0.4122(2) 0.8570(2) 0.0528(7) Uani 1 1 d . . . . .
H1 H 0.5657 0.4416 0.8801 0.063 Uiso 1 1 d . . . . .
C2 C 0.4086(4) 0.3911(2) 0.9207(3) 0.0635(9) Uani 1 1 d . . . . .
H2 H 0.4283 0.4068 0.9880 0.076 Uiso 1 1 d . . . . .
C3 C 0.2965(4) 0.3465(2) 0.8863(3) 0.0652(9) Uani 1 1 d . . . . .
H3 H 0.2430 0.3333 0.9316 0.078 Uiso 1 1 d . . . . .
C4 C 0.2627(3) 0.3219(2) 0.7878(3) 0.0587(8) Uani 1 1 d . . . . .
H4 H 0.1875 0.2922 0.7657 0.070 Uiso 1 1 d . . . . .
C5 C 0.3451(3) 0.34249(18) 0.7213(2) 0.0464(7) Uani 1 1 d . . . . .
C6 C 0.4571(3) 0.38813(16) 0.7566(2) 0.0419(6) Uani 1 1 d . . . . .
C7 C 0.4372(2) 0.35518(16) 0.5924(2) 0.0400(6) Uani 1 1 d . . . . .
C8 C 0.4759(2) 0.35053(17) 0.4987(2) 0.0424(6) Uani 1 1 d . . . . .
H8 H 0.4235 0.3240 0.4451 0.050 Uiso 1 1 d . . . . .
C9 C 0.5893(2) 0.38426(16) 0.4850(2) 0.0384(6) Uani 1 1 d . . . . .
C10 C 0.6648(2) 0.42657(17) 0.5682(2) 0.0415(6) Uani 1 1 d . . . . .
H10 H 0.7421 0.4503 0.5595 0.049 Uiso 1 1 d . . . . .
C11 C 0.6295(2) 0.43358(16) 0.6589(2) 0.0386(6) Uani 1 1 d . . . . .
C12 C 0.7096(2) 0.47930(17) 0.7435(2) 0.0404(6) Uani 1 1 d . . . . .
C13 C 0.6703(3) 0.55625(19) 0.7762(2) 0.0498(7) Uani 1 1 d . . . . .
H13 H 0.5898 0.5771 0.7493 0.059 Uiso 1 1 d . . . . .
C14 C 0.7505(4) 0.6017(2) 0.8483(3) 0.0591(9) Uani 1 1 d . . . . .
H14 H 0.7245 0.6535 0.8694 0.071 Uiso 1 1 d . . . . .
C15 C 0.8692(4) 0.5704(3) 0.8893(3) 0.0736(11) Uani 1 1 d . . . . .
H15 H 0.9228 0.6005 0.9388 0.088 Uiso 1 1 d . . . . .
C16 C 0.9082(4) 0.4951(3) 0.8574(3) 0.0760(11) Uani 1 1 d . . . . .
H16 H 0.9889 0.4747 0.8846 0.091 Uiso 1 1 d . . . . .
C17 C 0.8287(3) 0.4482(2) 0.7842(3) 0.0557(8) Uani 1 1 d . . . . .
H17 H 0.8556 0.3966 0.7632 0.066 Uiso 1 1 d . . . . .
C18 C 0.6352(2) 0.37855(16) 0.3879(2) 0.0393(6) Uani 1 1 d . . . . .
C19 C 0.6061(3) 0.30928(19) 0.3250(3) 0.0524(7) Uani 1 1 d . . . . .
H19 H 0.5591 0.2651 0.3449 0.062 Uiso 1 1 d . . . . .
C20 C 0.6459(3) 0.3055(2) 0.2333(3) 0.0624(9) Uani 1 1 d . . . . .
H20 H 0.6243 0.2589 0.1921 0.074 Uiso 1 1 d . . . . .
C21 C 0.7173(3) 0.3693(2) 0.2007(2) 0.0573(8) Uani 1 1 d . . . . .
C22 C 0.7611(5) 0.3648(4) 0.1002(3) 0.0969(15) Uani 1 1 d . . . . .
H22A H 0.8520 0.3555 0.1111 0.145 Uiso 1 1 d . . . . .
H22B H 0.7414 0.4165 0.0643 0.145 Uiso 1 1 d . . . . .
H22C H 0.7185 0.3191 0.0612 0.145 Uiso 1 1 d . . . . .
C23 C 0.7478(3) 0.4374(2) 0.2641(3) 0.0553(8) Uani 1 1 d . . . . .
H23 H 0.7964 0.4810 0.2448 0.066 Uiso 1 1 d . . . . .
C24 C 0.7079(3) 0.44206(17) 0.3559(2) 0.0477(7) Uani 1 1 d . . . . .
H24 H 0.7301 0.4887 0.3971 0.057 Uiso 1 1 d . . . . .
C25 C 0.9366(3) 0.6754(2) 0.5228(3) 0.0616(9) Uani 1 1 d . . . . .
H25 H 0.8576 0.7020 0.4880 0.074 Uiso 1 1 d . . . . .


_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
Cl1 C25 1.721(4) . ?
Cl2 C25 1.723(4) . ?
Cl3 C25 1.739(4) . ?
N1 C6 1.395(3) . ?
N1 C7 1.408(3) . ?
N1 C11 1.383(3) . ?
N2 C5 1.382(4) . ?
N2 C7 1.325(3) . ?
C1 C2 1.369(5) . ?
C1 C6 1.390(4) . ?
C2 C3 1.392(5) . ?
C3 C4 1.370(5) . ?
C4 C5 1.399(4) . ?
C5 C6 1.402(4) . ?
C7 C8 1.398(4) . ?
C8 C9 1.363(4) . ?
C9 C10 1.425(4) . ?
C9 C18 1.479(4) . ?
C10 C11 1.346(4) . ?
C11 C12 1.485(4) . ?
C12 C13 1.390(4) . ?
C12 C17 1.378(4) . ?
C13 C14 1.377(4) . ?
C14 C15 1.375(5) . ?
C15 C16 1.361(6) . ?
C16 C17 1.394(5) . ?
C18 C19 1.391(4) . ?
C18 C24 1.386(4) . ?
C19 C20 1.378(5) . ?
C20 C21 1.385(5) . ?
C21 C22 1.510(5) . ?
C21 C23 1.382(5) . ?
C23 C24 1.380(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C7 106.6(2) . . ?
C11 N1 C6 132.7(2) . . ?
C11 N1 C7 120.6(2) . . ?
C7 N2 C5 105.2(2) . . ?
C2 C1 C6 117.6(3) . . ?
C1 C2 C3 121.2(3) . . ?
C4 C3 C2 121.9(3) . . ?
C3 C4 C5 117.9(3) . . ?
N2 C5 C4 128.7(3) . . ?
N2 C5 C6 111.6(2) . . ?
C4 C5 C6 119.7(3) . . ?
N1 C6 C5 104.6(2) . . ?
C1 C6 N1 133.6(3) . . ?
C1 C6 C5 121.7(3) . . ?
N2 C7 N1 111.9(2) . . ?
N2 C7 C8 128.9(2) . . ?
C8 C7 N1 119.2(2) . . ?
C9 C8 C7 120.8(2) . . ?
C8 C9 C10 117.7(3) . . ?
C8 C9 C18 122.4(2) . . ?
C10 C9 C18 119.8(2) . . ?
C11 C10 C9 123.0(2) . . ?
N1 C11 C12 119.9(2) . . ?
C10 C11 N1 118.6(2) . . ?
C10 C11 C12 121.5(2) . . ?
C13 C12 C11 120.7(2) . . ?
C17 C12 C11 119.3(3) . . ?
C17 C12 C13 119.7(3) . . ?
C14 C13 C12 120.1(3) . . ?
C15 C14 C13 120.0(3) . . ?
C16 C15 C14 120.0(3) . . ?
C15 C16 C17 120.9(3) . . ?
C12 C17 C16 119.2(3) . . ?
C19 C18 C9 121.0(2) . . ?
C24 C18 C9 121.4(2) . . ?
C24 C18 C19 117.5(3) . . ?
C20 C19 C18 120.8(3) . . ?
C19 C20 C21 121.7(3) . . ?
C20 C21 C22 121.6(3) . . ?
C23 C21 C20 117.3(3) . . ?
C23 C21 C22 121.1(3) . . ?
C24 C23 C21 121.4(3) . . ?
C23 C24 C18 121.2(3) . . ?
Cl1 C25 Cl2 111.6(2) . . ?
Cl1 C25 Cl3 109.6(2) . . ?
Cl2 C25 Cl3 112.5(2) . . ?

_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 1.634
_oxdiff_exptl_absorpt_empirical_full_min 0.675
