# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_t_a
_database_code_depnum_ccdc_archive 'CCDC 1859746'
_audit_update_record             
;
2018-08-01 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H19 Cl N2 O'
_chemical_formula_sum            'C24 H19 Cl N2 O'
_chemical_formula_weight         386.86

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_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'

_cell_length_a                   5.628(2)
_cell_length_b                   19.385(4)
_cell_length_c                   17.569(4)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 91.36(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     1916.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9908
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      68.23

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.891
_shelx_estimated_absorpt_T_min   0.727
_shelx_estimated_absorpt_T_max   0.778
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE CMOS photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23435
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.395
_diffrn_reflns_theta_max         68.332
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3500
_reflns_number_gt                3116
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²+0.6423P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3500
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0819
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_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_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 0.13112(7) 0.41821(2) 0.51130(2) 0.03737(12) Uani 1 1 d . . . . .
C1 C 0.1002(2) 0.32597(7) 0.88142(7) 0.0280(3) Uani 1 1 d . . . . .
N1 N 0.1263(2) 0.39516(6) 0.89756(6) 0.0286(3) Uani 1 1 d . . . . .
O1 O 0.67465(16) 0.56465(5) 0.84782(5) 0.0306(2) Uani 1 1 d . . . . .
N2 N 0.47682(18) 0.60433(5) 0.81914(6) 0.0247(2) Uani 1 1 d . . . . .
C2 C -0.0885(3) 0.28954(8) 0.91476(8) 0.0356(3) Uani 1 1 d . . . . .
H2 H -0.1932 0.3127 0.9478 0.043 Uiso 1 1 calc R U . . .
C5 C 0.2197(3) 0.21882(8) 0.81908(8) 0.0374(3) Uani 1 1 d . . . . .
H5 H 0.3245 0.1943 0.7872 0.045 Uiso 1 1 calc R U . . .
C4 C 0.0344(3) 0.18529(8) 0.85201(8) 0.0401(4) Uani 1 1 d . . . . .
H4 H 0.0107 0.1375 0.8426 0.048 Uiso 1 1 calc R U . . .
C3 C -0.1205(3) 0.22082(8) 0.89945(9) 0.0404(4) Uani 1 1 d . . . . .
H3 H -0.2495 0.1969 0.9213 0.048 Uiso 1 1 calc R U . . .
C6 C 0.2548(2) 0.29023(7) 0.83263(8) 0.0305(3) Uani 1 1 d . . . . .
C7 C 0.4418(3) 0.32793(7) 0.80035(8) 0.0338(3) Uani 1 1 d . . . . .
H7 H 0.5489 0.3060 0.7671 0.041 Uiso 1 1 calc R U . . .
C8 C 0.4669(2) 0.39587(7) 0.81735(8) 0.0322(3) Uani 1 1 d . . . . .
H8 H 0.5932 0.4217 0.7965 0.039 Uiso 1 1 calc R U . . .
C9 C 0.3043(2) 0.42822(7) 0.86636(7) 0.0272(3) Uani 1 1 d . . . . .
C10 C 0.3300(2) 0.50394(7) 0.88532(7) 0.0282(3) Uani 1 1 d . . . . .
H10 H 0.2206 0.5151 0.9276 0.034 Uiso 1 1 calc R U . . .
C11 C 0.2765(2) 0.55560(7) 0.81711(7) 0.0239(3) Uani 1 1 d . . . . .
H11 H 0.1280 0.5816 0.8283 0.029 Uiso 1 1 calc R U . . .
C12 C 0.5836(3) 0.52487(7) 0.91014(8) 0.0346(3) Uani 1 1 d . . . . .
H12A H 0.5814 0.5529 0.9572 0.042 Uiso 1 1 calc R U . . .
H12B H 0.6831 0.4835 0.9197 0.042 Uiso 1 1 calc R U . . .
C13 C 0.2463(2) 0.52260(6) 0.73936(7) 0.0235(3) Uani 1 1 d . . . . .
C14 C 0.0403(2) 0.48500(7) 0.72318(8) 0.0287(3) Uani 1 1 d . . . . .
H14 H -0.0777 0.4813 0.7607 0.034 Uiso 1 1 calc R U . . .
C15 C 0.0039(2) 0.45289(7) 0.65352(8) 0.0308(3) Uani 1 1 d . . . . .
H15 H -0.1374 0.4274 0.6432 0.037 Uiso 1 1 calc R U . . .
C16 C 0.1762(2) 0.45846(7) 0.59930(7) 0.0283(3) Uani 1 1 d . . . . .
C17 C 0.3803(2) 0.49644(7) 0.61294(7) 0.0307(3) Uani 1 1 d . . . . .
H17 H 0.4961 0.5007 0.5747 0.037 Uiso 1 1 calc R U . . .
C18 C 0.4145(2) 0.52844(7) 0.68323(7) 0.0274(3) Uani 1 1 d . . . . .
H18 H 0.5547 0.5546 0.6929 0.033 Uiso 1 1 calc R U . . .
C19 C 0.4473(2) 0.66718(7) 0.86038(7) 0.0247(3) Uani 1 1 d . . . . .
C20 C 0.2460(2) 0.70706(7) 0.84410(8) 0.0305(3) Uani 1 1 d . . . . .
H20 H 0.1256 0.6901 0.8102 0.037 Uiso 1 1 calc R U . . .
C21 C 0.2215(3) 0.77140(7) 0.87729(9) 0.0348(3) Uani 1 1 d . . . . .
H21 H 0.0831 0.7981 0.8667 0.042 Uiso 1 1 calc R U . . .
C22 C 0.3977(3) 0.79701(7) 0.92584(8) 0.0353(3) Uani 1 1 d . . . . .
H22 H 0.3823 0.8416 0.9476 0.042 Uiso 1 1 calc R U . . .
C23 C 0.5962(3) 0.75732(8) 0.94244(9) 0.0367(3) Uani 1 1 d . . . . .
H23 H 0.7157 0.7745 0.9765 0.044 Uiso 1 1 calc R U . . .
C24 C 0.6229(2) 0.69249(7) 0.90987(8) 0.0310(3) Uani 1 1 d . . . . .
H24 H 0.7604 0.6656 0.9214 0.037 Uiso 1 1 calc R U . . .


_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 C16 1.7450(14) . ?
C1 N1 1.3780(18) . ?
C1 C2 1.414(2) . ?
C1 C6 1.417(2) . ?
N1 C9 1.3198(18) . ?
O1 N2 1.4348(15) . ?
O1 C12 1.4431(18) . ?
N2 C19 1.4292(17) . ?
N2 C11 1.4707(17) . ?
C2 C3 1.370(2) . ?
C2 H2 0.9500 . ?
C5 C4 1.368(2) . ?
C5 C6 1.418(2) . ?
C5 H5 0.9500 . ?
C4 C3 1.401(2) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C6 C7 1.411(2) . ?
C7 C8 1.357(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.417(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.5114(19) . ?
C10 C12 1.537(2) . ?
C10 C11 1.5852(18) . ?
C10 H10 1.0000 . ?
C11 C13 1.5143(18) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.3876(19) . ?
C13 C14 1.3931(19) . ?
C14 C15 1.384(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(2) . ?
C17 C18 1.3912(19) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.3905(19) . ?
C19 C20 1.396(2) . ?
C20 C21 1.385(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.385(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.391(2) . ?
C23 H23 0.9500 . ?
C24 H24 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
N1 C1 C2 118.58(13) . . ?
N1 C1 C6 122.45(12) . . ?
C2 C1 C6 118.97(13) . . ?
C9 N1 C1 117.73(12) . . ?
N2 O1 C12 105.45(10) . . ?
C19 N2 O1 112.18(10) . . ?
C19 N2 C11 117.48(10) . . ?
O1 N2 C11 104.62(9) . . ?
C3 C2 C1 120.06(15) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C5 C6 119.82(15) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C4 C3 120.60(14) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C2 C3 C4 120.93(14) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C7 C6 C1 117.67(13) . . ?
C7 C6 C5 122.72(14) . . ?
C1 C6 C5 119.60(13) . . ?
C8 C7 C6 119.27(13) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 119.85(13) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
N1 C9 C8 123.03(13) . . ?
N1 C9 C10 116.71(12) . . ?
C8 C9 C10 120.26(12) . . ?
C9 C10 C12 113.72(12) . . ?
C9 C10 C11 115.55(11) . . ?
C12 C10 C11 101.91(11) . . ?
C9 C10 H10 108.4 . . ?
C12 C10 H10 108.4 . . ?
C11 C10 H10 108.4 . . ?
N2 C11 C13 111.26(10) . . ?
N2 C11 C10 104.80(10) . . ?
C13 C11 C10 115.49(11) . . ?
N2 C11 H11 108.3 . . ?
C13 C11 H11 108.3 . . ?
C10 C11 H11 108.3 . . ?
O1 C12 C10 105.65(11) . . ?
O1 C12 H12A 110.6 . . ?
C10 C12 H12A 110.6 . . ?
O1 C12 H12B 110.6 . . ?
C10 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?
C18 C13 C14 118.43(12) . . ?
C18 C13 C11 122.89(12) . . ?
C14 C13 C11 118.68(11) . . ?
C15 C14 C13 121.38(13) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 118.93(13) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 121.16(12) . . ?
C15 C16 Cl1 119.14(11) . . ?
C17 C16 Cl1 119.68(11) . . ?
C16 C17 C18 119.27(13) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C13 C18 C17 120.80(12) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C24 C19 C20 119.63(12) . . ?
C24 C19 N2 121.89(12) . . ?
C20 C19 N2 118.16(12) . . ?
C21 C20 C19 120.06(13) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 120.36(14) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 119.60(13) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 120.75(14) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C19 C24 C23 119.60(13) . . ?
C19 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?

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
C2 C1 N1 C9 179.53(12) . . . . ?
C6 C1 N1 C9 -0.61(19) . . . . ?
C12 O1 N2 C19 85.03(12) . . . . ?
C12 O1 N2 C11 -43.39(12) . . . . ?
N1 C1 C2 C3 179.52(13) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
C6 C5 C4 C3 -0.4(2) . . . . ?
C1 C2 C3 C4 1.2(2) . . . . ?
C5 C4 C3 C2 -0.9(2) . . . . ?
N1 C1 C6 C7 0.30(19) . . . . ?
C2 C1 C6 C7 -179.84(12) . . . . ?
N1 C1 C6 C5 179.28(12) . . . . ?
C2 C1 C6 C5 -0.86(19) . . . . ?
C4 C5 C6 C7 -179.86(13) . . . . ?
C4 C5 C6 C1 1.2(2) . . . . ?
C1 C6 C7 C8 0.4(2) . . . . ?
C5 C6 C7 C8 -178.56(14) . . . . ?
C6 C7 C8 C9 -0.7(2) . . . . ?
C1 N1 C9 C8 0.25(19) . . . . ?
C1 N1 C9 C10 -179.64(11) . . . . ?
C7 C8 C9 N1 0.4(2) . . . . ?
C7 C8 C9 C10 -179.68(13) . . . . ?
N1 C9 C10 C12 131.21(13) . . . . ?
C8 C9 C10 C12 -48.68(17) . . . . ?
N1 C9 C10 C11 -111.41(13) . . . . ?
C8 C9 C10 C11 68.70(16) . . . . ?
C19 N2 C11 C13 140.52(11) . . . . ?
O1 N2 C11 C13 -94.34(11) . . . . ?
C19 N2 C11 C10 -93.99(12) . . . . ?
O1 N2 C11 C10 31.14(12) . . . . ?
C9 C10 C11 N2 -132.40(12) . . . . ?
C12 C10 C11 N2 -8.59(13) . . . . ?
C9 C10 C11 C13 -9.62(16) . . . . ?
C12 C10 C11 C13 114.20(12) . . . . ?
N2 O1 C12 C10 37.36(13) . . . . ?
C9 C10 C12 O1 108.31(12) . . . . ?
C11 C10 C12 O1 -16.73(13) . . . . ?
N2 C11 C13 C18 11.27(17) . . . . ?
C10 C11 C13 C18 -108.01(14) . . . . ?
N2 C11 C13 C14 -168.39(11) . . . . ?
C10 C11 C13 C14 72.33(15) . . . . ?
C18 C13 C14 C15 1.2(2) . . . . ?
C11 C13 C14 C15 -179.14(12) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C14 C15 C16 C17 -1.3(2) . . . . ?
C14 C15 C16 Cl1 -179.89(10) . . . . ?
C15 C16 C17 C18 1.3(2) . . . . ?
Cl1 C16 C17 C18 179.90(10) . . . . ?
C14 C13 C18 C17 -1.17(19) . . . . ?
C11 C13 C18 C17 179.17(12) . . . . ?
C16 C17 C18 C13 -0.1(2) . . . . ?
O1 N2 C19 C24 13.58(16) . . . . ?
C11 N2 C19 C24 134.87(13) . . . . ?
O1 N2 C19 C20 -172.94(10) . . . . ?
C11 N2 C19 C20 -51.66(16) . . . . ?
C24 C19 C20 C21 -0.2(2) . . . . ?
N2 C19 C20 C21 -173.79(12) . . . . ?
C19 C20 C21 C22 1.0(2) . . . . ?
C20 C21 C22 C23 -1.5(2) . . . . ?
C21 C22 C23 C24 1.2(2) . . . . ?
C20 C19 C24 C23 -0.1(2) . . . . ?
N2 C19 C24 C23 173.25(12) . . . . ?
C22 C23 C24 C19 -0.4(2) . . . . ?

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.041



####################################################################### 
# 
# 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_mo_dm14659_0m
_database_code_depnum_ccdc_archive 'CCDC 1859747'
_audit_update_record             
;
2018-08-01 deposited with the CCDC.
2018-09-03 downloaded from the CCDC.
;
_audit_creation_date             2014-11-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H19 Cl N2 O'
_chemical_formula_sum            'C24 H19 Cl N2 O'
_chemical_formula_weight         386.86
_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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'

_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                   5.7976(9)
_cell_length_b                   9.4263(14)
_cell_length_c                   17.097(3)
_cell_angle_alpha                87.715(3)
_cell_angle_beta                 87.737(3)
_cell_angle_gamma                86.465(3)
_cell_volume                     931.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1384
_cell_measurement_temperature    130
_cell_measurement_theta_max      26.363
_cell_measurement_theta_min      2.17
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.842
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0478 before and 0.0375 after correction.
The Ratio of minimum to maximum transmission is 0.8953.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9492
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.569
_diffrn_reflns_theta_min         1.193
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3455
_reflns_number_total             5658
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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         0.308
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5658
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.0969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1273
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_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 0.35786(10) 0.71009(6) 0.00023(3) 0.03585(15) Uani 1 1 d . . . . .
O1 O 0.6850(2) 1.03792(15) -0.33076(7) 0.0276(3) Uani 1 1 d . . . . .
N1 N 1.2276(3) 0.90422(16) -0.42114(8) 0.0233(3) Uani 1 1 d . . . . .
N2 N 0.7222(3) 1.08856(17) -0.25281(8) 0.0222(3) Uani 1 1 d . . . . .
C1 C 1.3717(3) 0.7841(2) -0.42284(10) 0.0222(4) Uani 1 1 d . . . . .
C2 C 1.5689(3) 0.7836(2) -0.47437(11) 0.0277(4) Uani 1 1 d . . . . .
H2 H 1.5976 0.8650 -0.5070 0.033 Uiso 1 1 calc R . . . .
C3 C 1.7175(4) 0.6657(2) -0.47693(12) 0.0336(5) Uani 1 1 d . . . . .
H3 H 1.8511 0.6663 -0.5109 0.040 Uiso 1 1 calc R . . . .
C4 C 1.6761(4) 0.5434(2) -0.43011(12) 0.0352(5) Uani 1 1 d . . . . .
H4 H 1.7804 0.4619 -0.4334 0.042 Uiso 1 1 calc R . . . .
C5 C 1.4876(4) 0.5408(2) -0.38010(11) 0.0305(5) Uani 1 1 d . . . . .
H5 H 1.4609 0.4577 -0.3486 0.037 Uiso 1 1 calc R . . . .
C6 C 1.3313(3) 0.6619(2) -0.37497(10) 0.0233(4) Uani 1 1 d . . . . .
C7 C 1.1333(3) 0.6668(2) -0.32413(11) 0.0265(4) Uani 1 1 d . . . . .
H7 H 1.0996 0.5866 -0.2911 0.032 Uiso 1 1 calc R . . . .
C8 C 0.9906(3) 0.7874(2) -0.32275(10) 0.0256(4) Uani 1 1 d . . . . .
H8 H 0.8567 0.7923 -0.2889 0.031 Uiso 1 1 calc R . . . .
C9 C 1.0447(3) 0.9048(2) -0.37235(10) 0.0223(4) Uani 1 1 d . . . . .
C10 C 0.9001(3) 1.0438(2) -0.37472(10) 0.0240(4) Uani 1 1 d . . . . .
H10 H 0.8677 1.0714 -0.4305 0.029 Uiso 1 1 calc R . . . .
C11 C 1.0179(3) 1.1637(2) -0.33845(11) 0.0262(4) Uani 1 1 d . . . . .
H11A H 0.9563 1.2579 -0.3585 0.031 Uiso 1 1 calc R . . . .
H11B H 1.1874 1.1552 -0.3487 0.031 Uiso 1 1 calc R . . . .
C12 C 0.9560(3) 1.14082(19) -0.25144(10) 0.0216(4) Uani 1 1 d . . . . .
H12 H 1.0642 1.0655 -0.2280 0.026 Uiso 1 1 calc R . . . .
C13 C 0.9546(3) 1.27408(19) -0.20508(10) 0.0223(4) Uani 1 1 d . . . . .
C14 C 1.1423(3) 1.2995(2) -0.16046(12) 0.0294(4) Uani 1 1 d . . . . .
H14 H 1.2715 1.2326 -0.1586 0.035 Uiso 1 1 calc R . . . .
C15 C 1.1403(4) 1.4229(2) -0.11863(12) 0.0331(5) Uani 1 1 d . . . . .
H15 H 1.2691 1.4404 -0.0885 0.040 Uiso 1 1 calc R . . . .
C16 C 0.9531(4) 1.5203(2) -0.12039(12) 0.0326(5) Uani 1 1 d . . . . .
H16 H 0.9522 1.6040 -0.0912 0.039 Uiso 1 1 calc R . . . .
C17 C 0.7674(4) 1.4957(2) -0.16467(12) 0.0310(5) Uani 1 1 d . . . . .
H17 H 0.6385 1.5629 -0.1664 0.037 Uiso 1 1 calc R . . . .
C18 C 0.7685(3) 1.3728(2) -0.20673(11) 0.0261(4) Uani 1 1 d . . . . .
H18 H 0.6396 1.3563 -0.2370 0.031 Uiso 1 1 calc R . . . .
C19 C 0.6505(3) 0.99019(19) -0.19433(10) 0.0200(4) Uani 1 1 d . . . . .
C20 C 0.4683(3) 0.90506(19) -0.20762(11) 0.0219(4) Uani 1 1 d . . . . .
H20 H 0.4047 0.9064 -0.2580 0.026 Uiso 1 1 calc R . . . .
C21 C 0.3803(3) 0.8192(2) -0.14802(11) 0.0241(4) Uani 1 1 d . . . . .
H21 H 0.2554 0.7620 -0.1572 0.029 Uiso 1 1 calc R . . . .
C22 C 0.4736(3) 0.8162(2) -0.07492(11) 0.0249(4) Uani 1 1 d . . . . .
C23 C 0.6574(3) 0.8974(2) -0.06091(11) 0.0261(4) Uani 1 1 d . . . . .
H23 H 0.7230 0.8934 -0.0108 0.031 Uiso 1 1 calc R . . . .
C24 C 0.7447(3) 0.9844(2) -0.12040(10) 0.0238(4) Uani 1 1 d . . . . .
H24 H 0.8702 1.0408 -0.1109 0.029 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
Cl1 C22 1.7359(19) . ?
O1 N2 1.4617(19) . ?
O1 C10 1.433(2) . ?
N1 C1 1.365(2) . ?
N1 C9 1.323(2) . ?
N2 C12 1.472(2) . ?
N2 C19 1.405(2) . ?
C1 C2 1.415(3) . ?
C1 C6 1.413(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.365(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.405(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.362(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.416(3) . ?
C6 C7 1.412(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.365(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.410(3) . ?
C9 C10 1.511(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.521(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.527(2) . ?
C12 H12 1.0000 . ?
C12 C13 1.511(2) . ?
C13 C14 1.391(3) . ?
C13 C18 1.381(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.378(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.396(2) . ?
C19 C24 1.395(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.380(3) . ?
C22 C23 1.384(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.381(3) . ?
C24 H24 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
C10 O1 N2 107.26(13) . . ?
C9 N1 C1 118.10(16) . . ?
O1 N2 C12 109.07(13) . . ?
C19 N2 O1 110.89(13) . . ?
C19 N2 C12 119.41(15) . . ?
N1 C1 C2 118.29(17) . . ?
N1 C1 C6 122.42(17) . . ?
C6 C1 C2 119.29(18) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.73(19) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.1(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.35(17) . . ?
C7 C6 C1 117.61(18) . . ?
C7 C6 C5 123.04(18) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.52(18) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.05(18) . . ?
C9 C8 H8 120.5 . . ?
N1 C9 C8 123.29(18) . . ?
N1 C9 C10 113.40(16) . . ?
C8 C9 C10 123.30(17) . . ?
O1 C10 C9 113.44(16) . . ?
O1 C10 H10 108.9 . . ?
O1 C10 C11 103.66(14) . . ?
C9 C10 H10 108.9 . . ?
C9 C10 C11 112.73(16) . . ?
C11 C10 H10 108.9 . . ?
C10 C11 H11A 111.3 . . ?
C10 C11 H11B 111.3 . . ?
C10 C11 C12 102.26(14) . . ?
H11A C11 H11B 109.2 . . ?
C12 C11 H11A 111.3 . . ?
C12 C11 H11B 111.3 . . ?
N2 C12 C11 102.29(14) . . ?
N2 C12 H12 109.8 . . ?
N2 C12 C13 110.82(15) . . ?
C11 C12 H12 109.8 . . ?
C13 C12 C11 114.04(15) . . ?
C13 C12 H12 109.8 . . ?
C14 C13 C12 120.31(17) . . ?
C18 C13 C12 120.67(17) . . ?
C18 C13 C14 119.02(18) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.87(19) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.61(19) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.66(19) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 120.81(19) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 N2 119.83(16) . . ?
C24 C19 N2 121.01(16) . . ?
C24 C19 C20 118.92(17) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.35(17) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 119.95(17) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 Cl1 119.56(15) . . ?
C21 C22 C23 120.65(17) . . ?
C23 C22 Cl1 119.78(15) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.48(17) . . ?
C24 C23 H23 120.3 . . ?
C19 C24 H24 119.7 . . ?
C23 C24 C19 120.62(17) . . ?
C23 C24 H24 119.7 . . ?

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
Cl1 C22 C23 C24 -178.32(15) . . . . ?
O1 N2 C12 C11 18.40(18) . . . . ?
O1 N2 C12 C13 140.34(15) . . . . ?
O1 N2 C19 C20 -30.7(2) . . . . ?
O1 N2 C19 C24 154.89(16) . . . . ?
O1 C10 C11 C12 39.12(18) . . . . ?
N1 C1 C2 C3 179.39(17) . . . . ?
N1 C1 C6 C5 179.71(16) . . . . ?
N1 C1 C6 C7 0.1(3) . . . . ?
N1 C9 C10 O1 171.38(14) . . . . ?
N1 C9 C10 C11 -71.19(19) . . . . ?
N2 O1 C10 C9 94.35(16) . . . . ?
N2 O1 C10 C11 -28.25(18) . . . . ?
N2 C12 C13 C14 144.99(17) . . . . ?
N2 C12 C13 C18 -35.5(2) . . . . ?
N2 C19 C20 C21 -173.11(16) . . . . ?
N2 C19 C24 C23 173.53(17) . . . . ?
C1 N1 C9 C8 -0.6(3) . . . . ?
C1 N1 C9 C10 179.17(15) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C1 C6 C7 C8 -0.3(3) . . . . ?
C2 C1 C6 C5 -0.7(3) . . . . ?
C2 C1 C6 C7 179.76(16) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C4 C5 C6 C7 -179.67(18) . . . . ?
C5 C6 C7 C8 -179.83(18) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 N1 0.4(3) . . . . ?
C7 C8 C9 C10 -179.28(17) . . . . ?
C8 C9 C10 O1 -8.9(2) . . . . ?
C8 C9 C10 C11 108.6(2) . . . . ?
C9 N1 C1 C2 -179.35(16) . . . . ?
C9 N1 C1 C6 0.3(2) . . . . ?
C9 C10 C11 C12 -83.95(18) . . . . ?
C10 O1 N2 C12 6.15(18) . . . . ?
C10 O1 N2 C19 -127.33(15) . . . . ?
C10 C11 C12 N2 -34.53(18) . . . . ?
C10 C11 C12 C13 -154.24(16) . . . . ?
C11 C12 C13 C14 -100.2(2) . . . . ?
C11 C12 C13 C18 79.3(2) . . . . ?
C12 N2 C19 C20 -158.81(16) . . . . ?
C12 N2 C19 C24 26.8(2) . . . . ?
C12 C13 C14 C15 179.41(17) . . . . ?
C12 C13 C18 C17 -179.54(17) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C13 C18 C17 0.0(3) . . . . ?
C14 C15 C16 C17 -0.7(3) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C16 C17 C18 C13 -0.2(3) . . . . ?
C18 C13 C14 C15 -0.2(3) . . . . ?
C19 N2 C12 C11 147.31(16) . . . . ?
C19 N2 C12 C13 -90.76(19) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
C20 C19 C24 C23 -0.9(3) . . . . ?
C20 C21 C22 Cl1 178.80(14) . . . . ?
C20 C21 C22 C23 -0.8(3) . . . . ?
C21 C22 C23 C24 1.3(3) . . . . ?
C22 C23 C24 C19 -0.4(3) . . . . ?
C24 C19 C20 C21 1.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
