# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_cu_20181219LMF_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1887161'
loop_
_audit_author_name
_audit_author_address
'Ying He'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2018-12-24 deposited with the CCDC.	2019-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Cl N O2'
_chemical_formula_weight         387.84

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.0263(5)
_cell_length_b                   16.9680(14)
_cell_length_c                   18.8850(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1931.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5712
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      68.36

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.904
_shelx_estimated_absorpt_T_min   0.679
_shelx_estimated_absorpt_T_max   0.750
_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      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10368
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.502
_diffrn_reflns_theta_max         65.485
_diffrn_reflns_theta_full        65.486
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             3213
_reflns_number_gt                3040
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_max     0.930
_reflns_Friedel_fraction_full    0.930

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0836P)²] 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_abs_structure_details 
;
 Flack x determined using 1145 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.031(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3213
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.30896(19) 0.69505(6) 0.29654(4) 0.0711(3) Uani 1 1 d . . . . .
O2 O 0.0580(3) 0.55174(11) 0.65771(10) 0.0444(4) Uani 1 1 d . . . . .
O1 O 0.0227(4) 0.46927(14) 0.56593(12) 0.0584(6) Uani 1 1 d . . . . .
N1 N 0.3820(4) 0.49950(12) 0.70591(12) 0.0388(5) Uani 1 1 d . . . . .
C11 C 0.1175(5) 0.56430(14) 0.78432(14) 0.0401(6) Uani 1 1 d . . . . .
C10 C 0.2261(4) 0.56418(14) 0.71233(14) 0.0387(5) Uani 1 1 d . . . . .
C6 C 0.4960(5) 0.65723(12) 0.49665(14) 0.0382(5) Uani 1 1 d . . . . .
C23 C 0.3262(4) 0.45719(14) 0.65301(13) 0.0385(5) Uani 1 1 d . . . . .
C9 C 0.3430(5) 0.64326(15) 0.69547(15) 0.0440(6) Uani 1 1 d . . . . .
H9A H 0.232848 0.684846 0.692928 0.053 Uiso 1 1 calc R U . . .
H9B H 0.444882 0.656024 0.733549 0.053 Uiso 1 1 calc R U . . .
C24 C 0.1202(5) 0.48974(15) 0.61776(15) 0.0414(6) Uani 1 1 d . . . . .
C22 C 0.4456(5) 0.38577(15) 0.63133(14) 0.0407(6) Uani 1 1 d . . . . .
C2 C 0.7978(5) 0.61849(17) 0.42042(18) 0.0511(7) Uani 1 1 d . . . . .
H2 H 0.940191 0.598189 0.415111 0.061 Uiso 1 1 calc R U . . .
C12 C 0.2250(5) 0.53442(15) 0.84255(16) 0.0482(7) Uani 1 1 d . . . . .
H12 H 0.364459 0.511709 0.837237 0.058 Uiso 1 1 calc R U . . .
C5 C 0.3789(4) 0.68028(14) 0.43693(14) 0.0406(6) Uani 1 1 d . . . . .
H5 H 0.238606 0.702425 0.441891 0.049 Uiso 1 1 calc R U . . .
C8 C 0.4678(5) 0.63999(15) 0.62729(16) 0.0449(6) Uani 1 1 d . . . . .
H8 H 0.610553 0.619223 0.628123 0.054 Uiso 1 1 calc R U . . .
C7 C 0.3897(5) 0.66442(14) 0.56618(15) 0.0409(6) Uani 1 1 d . . . . .
H7 H 0.251832 0.689005 0.567121 0.049 Uiso 1 1 calc R U . . .
C17 C 0.6492(5) 0.36915(18) 0.66294(16) 0.0501(7) Uani 1 1 d . . . . .
H17 H 0.709756 0.404559 0.695182 0.060 Uiso 1 1 calc R U . . .
C1 C 0.7098(5) 0.62618(14) 0.48748(17) 0.0448(6) Uani 1 1 d . . . . .
H1 H 0.792365 0.610737 0.526701 0.054 Uiso 1 1 calc R U . . .
C3 C 0.6794(6) 0.64025(17) 0.36108(16) 0.0520(7) Uani 1 1 d . . . . .
H3 H 0.739740 0.634615 0.316035 0.062 Uiso 1 1 calc R U . . .
C21 C 0.3612(6) 0.33333(17) 0.58191(17) 0.0538(7) Uani 1 1 d . . . . .
H21 H 0.227435 0.344214 0.559354 0.065 Uiso 1 1 calc R U . . .
C4 C 0.4681(5) 0.67074(15) 0.37039(15) 0.0466(6) Uani 1 1 d . . . . .
C16 C -0.0900(6) 0.5979(2) 0.79308(19) 0.0636(9) Uani 1 1 d . . . . .
H16 H -0.164848 0.618991 0.754395 0.076 Uiso 1 1 calc R U . . .
C13 C 0.1283(8) 0.53764(17) 0.90937(16) 0.0608(9) Uani 1 1 d . . . . .
H13 H 0.203313 0.517608 0.948469 0.073 Uiso 1 1 calc R U . . .
C20 C 0.4752(8) 0.26494(19) 0.5661(2) 0.0671(10) Uani 1 1 d . . . . .
H20 H 0.417004 0.229760 0.533204 0.081 Uiso 1 1 calc R U . . .
C19 C 0.6742(7) 0.24845(19) 0.59854(19) 0.0636(10) Uani 1 1 d . . . . .
H19 H 0.749703 0.202136 0.587915 0.076 Uiso 1 1 calc R U . . .
C14 C -0.0780(7) 0.57050(19) 0.91731(18) 0.0625(9) Uani 1 1 d . . . . .
H14 H -0.143874 0.572500 0.961813 0.075 Uiso 1 1 calc R U . . .
C15 C -0.1860(6) 0.6001(3) 0.8602(2) 0.0747(11) Uani 1 1 d . . . . .
H15 H -0.326193 0.622154 0.865855 0.090 Uiso 1 1 calc R U . . .
C18 C 0.7612(6) 0.3009(2) 0.6469(2) 0.0609(8) Uani 1 1 d . . . . .
H18 H 0.896147 0.290043 0.668744 0.073 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 C4 1.742(3) . ?
O2 C24 1.348(3) . ?
O2 C10 1.461(3) . ?
O1 C24 1.193(4) . ?
N1 C23 1.275(4) . ?
N1 C10 1.450(3) . ?
C11 C12 1.373(4) . ?
C11 C16 1.385(5) . ?
C11 C10 1.509(4) . ?
C10 C9 1.549(4) . ?
C6 C5 1.387(4) . ?
C6 C1 1.403(4) . ?
C6 C7 1.466(4) . ?
C23 C22 1.468(4) . ?
C23 C24 1.513(4) . ?
C9 C8 1.492(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C22 C21 1.386(4) . ?
C22 C17 1.393(4) . ?
C2 C3 1.379(5) . ?
C2 C1 1.379(5) . ?
C2 H2 0.9300 . ?
C12 C13 1.391(5) . ?
C12 H12 0.9300 . ?
C5 C4 1.376(4) . ?
C5 H5 0.9300 . ?
C8 C7 1.313(4) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
C17 C18 1.375(4) . ?
C17 H17 0.9300 . ?
C1 H1 0.9300 . ?
C3 C4 1.386(5) . ?
C3 H3 0.9300 . ?
C21 C20 1.381(5) . ?
C21 H21 0.9300 . ?
C16 C15 1.393(5) . ?
C16 H16 0.9300 . ?
C13 C14 1.371(6) . ?
C13 H13 0.9300 . ?
C20 C19 1.375(6) . ?
C20 H20 0.9300 . ?
C19 C18 1.379(6) . ?
C19 H19 0.9300 . ?
C14 C15 1.357(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
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
C24 O2 C10 108.37(19) . . ?
C23 N1 C10 108.7(2) . . ?
C12 C11 C16 118.8(3) . . ?
C12 C11 C10 121.1(3) . . ?
C16 C11 C10 120.0(3) . . ?
N1 C10 O2 106.3(2) . . ?
N1 C10 C11 110.9(2) . . ?
O2 C10 C11 109.6(2) . . ?
N1 C10 C9 110.1(2) . . ?
O2 C10 C9 107.2(2) . . ?
C11 C10 C9 112.4(2) . . ?
C5 C6 C1 118.2(3) . . ?
C5 C6 C7 118.9(2) . . ?
C1 C6 C7 122.9(3) . . ?
N1 C23 C22 123.6(2) . . ?
N1 C23 C24 110.8(2) . . ?
C22 C23 C24 125.5(2) . . ?
C8 C9 C10 112.0(2) . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
O1 C24 O2 123.3(3) . . ?
O1 C24 C23 131.2(3) . . ?
O2 C24 C23 105.5(2) . . ?
C21 C22 C17 118.8(3) . . ?
C21 C22 C23 122.5(3) . . ?
C17 C22 C23 118.6(3) . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C8 C9 124.5(3) . . ?
C7 C8 H8 117.8 . . ?
C9 C8 H8 117.8 . . ?
C8 C7 C6 127.2(2) . . ?
C8 C7 H7 116.4 . . ?
C6 C7 H7 116.4 . . ?
C18 C17 C22 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C22 C17 H17 119.7 . . ?
C2 C1 C6 120.1(3) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C2 C3 C4 118.2(3) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 Cl1 119.2(2) . . ?
C3 C4 Cl1 119.5(2) . . ?
C11 C16 C15 119.7(4) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C14 C13 C12 119.7(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.9(4) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.077



