# 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_mo_gd_lxl34_0m
_database_code_depnum_ccdc_archive 'CCDC 1832338'
_audit_update_record             
;
2018-11-04 deposited with the CCDC.
2018-12-05 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 Br N2 O'
_chemical_formula_sum            'C24 H19 Br N2 O'
_chemical_formula_weight         431.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   13.0718(11)
_cell_length_b                   15.5471(13)
_cell_length_c                   10.5005(9)
_cell_angle_alpha                90
_cell_angle_beta                 113.1810(10)
_cell_angle_gamma                90
_cell_volume                     1961.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4245
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      28.36

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   0.2399
_exptl_transmission_factor_max   0.3375
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.112
_shelx_estimated_absorpt_T_min   0.517
_shelx_estimated_absorpt_T_max   0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21919
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.695
_diffrn_reflns_theta_max         31.093
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5867
_reflns_number_gt                4239
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0290P)²+2.0675P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5867
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
Br1 Br 0.43473(2) 0.34050(2) 1.56570(2) 0.02992(8) Uani 1 1 d . . . . .
O1 O 0.06169(12) 0.43943(10) 0.89515(15) 0.0181(3) Uani 1 1 d . . . . .
N1 N 0.12548(15) 0.55834(12) 1.03468(18) 0.0175(4) Uani 1 1 d . . . . .
H5 H 0.0750 0.5597 1.0706 0.021 Uiso 1 1 calc R U . . .
N2 N 0.16556(16) 0.52911(12) 0.52899(18) 0.0198(4) Uani 1 1 d . . . . .
C1 C 0.3969(2) 0.37123(15) 1.3772(2) 0.0204(5) Uani 1 1 d . . . . .
C2 C 0.4626(2) 0.42852(15) 1.3444(2) 0.0224(5) Uani 1 1 d . . . . .
H2 H 0.5262 0.4532 1.4151 0.027 Uiso 1 1 calc R U . . .
C3 C 0.43489(19) 0.45008(15) 1.2058(2) 0.0204(4) Uani 1 1 d . . . . .
H3 H 0.4794 0.4904 1.1827 0.024 Uiso 1 1 calc R U . . .
C4 C 0.34342(18) 0.41365(14) 1.1012(2) 0.0169(4) Uani 1 1 d . . . . .
C5 C 0.30981(18) 0.43857(15) 0.9507(2) 0.0187(4) Uani 1 1 d . . . . .
H17 H 0.2732 0.3887 0.8917 0.022 Uiso 1 1 calc R U . . .
H4 H 0.3777 0.4522 0.9344 0.022 Uiso 1 1 calc R U . . .
C6 C 0.22989(17) 0.51687(14) 0.9062(2) 0.0158(4) Uani 1 1 d . . . . .
C7 C 0.19002(18) 0.53545(14) 0.7536(2) 0.0171(4) Uani 1 1 d . . . . .
C8 C 0.10853(18) 0.59921(14) 0.6781(2) 0.0182(4) Uani 1 1 d . . . . .
C9 C 0.0456(2) 0.66082(15) 0.7135(2) 0.0225(5) Uani 1 1 d . . . . .
H16 H 0.0529 0.6670 0.8067 0.027 Uiso 1 1 calc R U . . .
C10 C -0.0266(2) 0.71201(17) 0.6109(3) 0.0292(6) Uani 1 1 d . . . . .
H10 H -0.0698 0.7537 0.6337 0.035 Uiso 1 1 calc R U . . .
C11 C -0.0379(2) 0.70405(16) 0.4729(2) 0.0273(5) Uani 1 1 d . . . . .
H1 H -0.0882 0.7409 0.4046 0.033 Uiso 1 1 calc R U . . .
C12 C 0.3057(2) 0.33332(16) 1.2758(2) 0.0242(5) Uani 1 1 d . . . . .
H19 H 0.2612 0.2934 1.2997 0.029 Uiso 1 1 calc R U . . .
C13 C 0.28019(19) 0.35456(15) 1.1378(2) 0.0222(5) Uani 1 1 d . . . . .
H18 H 0.2182 0.3280 1.0673 0.027 Uiso 1 1 calc R U . . .
C14 C 0.12847(17) 0.49868(14) 0.9428(2) 0.0146(4) Uani 1 1 d . . . . .
C15 C 0.21304(18) 0.61824(14) 1.0661(2) 0.0180(4) Uani 1 1 d . . . . .
C16 C 0.27793(18) 0.59640(14) 0.9933(2) 0.0172(4) Uani 1 1 d . . . . .
C17 C 0.3680(2) 0.64720(16) 1.0054(2) 0.0244(5) Uani 1 1 d . . . . .
H9 H 0.4136 0.6333 0.9568 0.029 Uiso 1 1 calc R U . . .
C18 C 0.3903(2) 0.71948(17) 1.0909(3) 0.0306(6) Uani 1 1 d . . . . .
H8 H 0.4523 0.7548 1.1011 0.037 Uiso 1 1 calc R U . . .
C19 C 0.3241(2) 0.74052(16) 1.1609(3) 0.0313(6) Uani 1 1 d . . . . .
H7 H 0.3405 0.7907 1.2171 0.038 Uiso 1 1 calc R U . . .
C20 C 0.2337(2) 0.68960(16) 1.1507(2) 0.0256(5) Uani 1 1 d . . . . .
H6 H 0.1882 0.7033 1.1996 0.031 Uiso 1 1 calc R U . . .
C21 C 0.0220(2) 0.64433(15) 0.4336(2) 0.0246(5) Uani 1 1 d . . . . .
H15 H 0.0137 0.6388 0.3399 0.029 Uiso 1 1 calc R U . . .
C22 C 0.09535(18) 0.59246(15) 0.5380(2) 0.0189(4) Uani 1 1 d . . . . .
C23 C 0.1782(2) 0.50365(18) 0.4035(2) 0.0297(6) Uani 1 1 d . . . . .
H12 H 0.1047 0.4973 0.3283 0.045 Uiso 1 1 calc R U . . .
H11 H 0.2180 0.4487 0.4188 0.045 Uiso 1 1 calc R U . . .
H13 H 0.2206 0.5477 0.3784 0.045 Uiso 1 1 calc R U . . .
C24 C 0.22099(19) 0.49520(15) 0.6593(2) 0.0210(5) Uani 1 1 d . . . . .
H14 H 0.2738 0.4498 0.6805 0.025 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
Br1 C1 1.902(2) . ?
O1 C14 1.232(3) . ?
N1 C14 1.350(3) . ?
N1 C15 1.410(3) . ?
N1 H5 0.8800 . ?
N2 C24 1.376(3) . ?
N2 C22 1.375(3) . ?
N2 C23 1.446(3) . ?
C1 C2 1.373(3) . ?
C1 C12 1.379(3) . ?
C2 C3 1.395(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C13 1.387(3) . ?
C4 C5 1.515(3) . ?
C5 C6 1.552(3) . ?
C5 H17 0.9900 . ?
C5 H4 0.9900 . ?
C6 C7 1.506(3) . ?
C6 C16 1.519(3) . ?
C6 C14 1.545(3) . ?
C7 C24 1.361(3) . ?
C7 C8 1.442(3) . ?
C8 C9 1.404(3) . ?
C8 C22 1.416(3) . ?
C9 C10 1.373(3) . ?
C9 H16 0.9500 . ?
C10 C11 1.403(3) . ?
C10 H10 0.9500 . ?
C11 C21 1.378(3) . ?
C11 H1 0.9500 . ?
C12 C13 1.392(3) . ?
C12 H19 0.9500 . ?
C13 H18 0.9500 . ?
C15 C20 1.380(3) . ?
C15 C16 1.389(3) . ?
C16 C17 1.382(3) . ?
C17 C18 1.396(4) . ?
C17 H9 0.9500 . ?
C18 C19 1.377(4) . ?
C18 H8 0.9500 . ?
C19 C20 1.391(4) . ?
C19 H7 0.9500 . ?
C20 H6 0.9500 . ?
C21 C22 1.395(3) . ?
C21 H15 0.9500 . ?
C23 H12 0.9800 . ?
C23 H11 0.9800 . ?
C23 H13 0.9800 . ?
C24 H14 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
C14 N1 C15 111.82(17) . . ?
C14 N1 H5 124.1 . . ?
C15 N1 H5 124.1 . . ?
C24 N2 C22 108.08(18) . . ?
C24 N2 C23 126.61(19) . . ?
C22 N2 C23 125.31(19) . . ?
C2 C1 C12 121.3(2) . . ?
C2 C1 Br1 119.51(18) . . ?
C12 C1 Br1 119.19(18) . . ?
C1 C2 C3 119.1(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C13 118.3(2) . . ?
C3 C4 C5 121.8(2) . . ?
C13 C4 C5 119.9(2) . . ?
C4 C5 C6 113.53(17) . . ?
C4 C5 H17 108.9 . . ?
C6 C5 H17 108.9 . . ?
C4 C5 H4 108.9 . . ?
C6 C5 H4 108.9 . . ?
H17 C5 H4 107.7 . . ?
C7 C6 C16 111.87(17) . . ?
C7 C6 C14 109.17(17) . . ?
C16 C6 C14 101.03(16) . . ?
C7 C6 C5 112.40(17) . . ?
C16 C6 C5 112.81(17) . . ?
C14 C6 C5 108.88(17) . . ?
C24 C7 C8 106.46(19) . . ?
C24 C7 C6 127.5(2) . . ?
C8 C7 C6 126.01(19) . . ?
C9 C8 C22 118.7(2) . . ?
C9 C8 C7 134.9(2) . . ?
C22 C8 C7 106.33(19) . . ?
C10 C9 C8 118.8(2) . . ?
C10 C9 H16 120.6 . . ?
C8 C9 H16 120.6 . . ?
C9 C10 C11 121.3(2) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C21 C11 C10 121.8(2) . . ?
C21 C11 H1 119.1 . . ?
C10 C11 H1 119.1 . . ?
C1 C12 C13 118.9(2) . . ?
C1 C12 H19 120.6 . . ?
C13 C12 H19 120.6 . . ?
C4 C13 C12 121.3(2) . . ?
C4 C13 H18 119.3 . . ?
C12 C13 H18 119.3 . . ?
O1 C14 N1 126.07(19) . . ?
O1 C14 C6 125.20(19) . . ?
N1 C14 C6 108.73(17) . . ?
C20 C15 C16 122.9(2) . . ?
C20 C15 N1 128.1(2) . . ?
C16 C15 N1 108.96(19) . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 C6 131.0(2) . . ?
C15 C16 C6 109.45(18) . . ?
C16 C17 C18 118.3(2) . . ?
C16 C17 H9 120.9 . . ?
C18 C17 H9 120.9 . . ?
C19 C18 C17 121.3(2) . . ?
C19 C18 H8 119.4 . . ?
C17 C18 H8 119.4 . . ?
C18 C19 C20 121.1(2) . . ?
C18 C19 H7 119.4 . . ?
C20 C19 H7 119.4 . . ?
C15 C20 C19 116.9(2) . . ?
C15 C20 H6 121.6 . . ?
C19 C20 H6 121.6 . . ?
C11 C21 C22 116.7(2) . . ?
C11 C21 H15 121.6 . . ?
C22 C21 H15 121.6 . . ?
N2 C22 C21 129.1(2) . . ?
N2 C22 C8 108.26(19) . . ?
C21 C22 C8 122.6(2) . . ?
N2 C23 H12 109.5 . . ?
N2 C23 H11 109.5 . . ?
H12 C23 H11 109.5 . . ?
N2 C23 H13 109.5 . . ?
H12 C23 H13 109.5 . . ?
H11 C23 H13 109.5 . . ?
C7 C24 N2 110.9(2) . . ?
C7 C24 H14 124.6 . . ?
N2 C24 H14 124.6 . . ?

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
C12 C1 C2 C3 1.5(3) . . . . ?
Br1 C1 C2 C3 179.42(17) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 C13 -0.4(3) . . . . ?
C2 C3 C4 C5 177.9(2) . . . . ?
C3 C4 C5 C6 -88.2(3) . . . . ?
C13 C4 C5 C6 90.0(2) . . . . ?
C4 C5 C6 C7 -175.03(18) . . . . ?
C4 C5 C6 C16 57.3(2) . . . . ?
C4 C5 C6 C14 -53.9(2) . . . . ?
C16 C6 C7 C24 124.3(2) . . . . ?
C14 C6 C7 C24 -124.8(2) . . . . ?
C5 C6 C7 C24 -3.8(3) . . . . ?
C16 C6 C7 C8 -57.2(3) . . . . ?
C14 C6 C7 C8 53.8(3) . . . . ?
C5 C6 C7 C8 174.7(2) . . . . ?
C24 C7 C8 C9 -179.9(3) . . . . ?
C6 C7 C8 C9 1.3(4) . . . . ?
C24 C7 C8 C22 0.2(2) . . . . ?
C6 C7 C8 C22 -178.6(2) . . . . ?
C22 C8 C9 C10 0.2(3) . . . . ?
C7 C8 C9 C10 -179.7(3) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C21 0.5(4) . . . . ?
C2 C1 C12 C13 -0.5(4) . . . . ?
Br1 C1 C12 C13 -178.45(17) . . . . ?
C3 C4 C13 C12 1.4(3) . . . . ?
C5 C4 C13 C12 -176.9(2) . . . . ?
C1 C12 C13 C4 -1.0(4) . . . . ?
C15 N1 C14 O1 -178.9(2) . . . . ?
C15 N1 C14 C6 1.0(2) . . . . ?
C7 C6 C14 O1 61.2(3) . . . . ?
C16 C6 C14 O1 179.3(2) . . . . ?
C5 C6 C14 O1 -61.8(3) . . . . ?
C7 C6 C14 N1 -118.62(19) . . . . ?
C16 C6 C14 N1 -0.6(2) . . . . ?
C5 C6 C14 N1 118.34(19) . . . . ?
C14 N1 C15 C20 177.1(2) . . . . ?
C14 N1 C15 C16 -1.0(2) . . . . ?
C20 C15 C16 C17 0.5(3) . . . . ?
N1 C15 C16 C17 178.68(19) . . . . ?
C20 C15 C16 C6 -177.7(2) . . . . ?
N1 C15 C16 C6 0.5(2) . . . . ?
C7 C6 C16 C17 -61.8(3) . . . . ?
C14 C6 C16 C17 -177.8(2) . . . . ?
C5 C6 C16 C17 66.1(3) . . . . ?
C7 C6 C16 C15 116.1(2) . . . . ?
C14 C6 C16 C15 0.0(2) . . . . ?
C5 C6 C16 C15 -116.0(2) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C6 C16 C17 C18 177.5(2) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C20 1.1(4) . . . . ?
C16 C15 C20 C19 0.1(4) . . . . ?
N1 C15 C20 C19 -177.8(2) . . . . ?
C18 C19 C20 C15 -0.8(4) . . . . ?
C10 C11 C21 C22 -0.6(4) . . . . ?
C24 N2 C22 C21 -179.4(2) . . . . ?
C23 N2 C22 C21 0.8(4) . . . . ?
C24 N2 C22 C8 0.9(3) . . . . ?
C23 N2 C22 C8 -178.8(2) . . . . ?
C11 C21 C22 N2 -179.1(2) . . . . ?
C11 C21 C22 C8 0.5(4) . . . . ?
C9 C8 C22 N2 179.4(2) . . . . ?
C7 C8 C22 N2 -0.7(2) . . . . ?
C9 C8 C22 C21 -0.3(3) . . . . ?
C7 C8 C22 C21 179.7(2) . . . . ?
C8 C7 C24 N2 0.4(3) . . . . ?
C6 C7 C24 N2 179.2(2) . . . . ?
C22 N2 C24 C7 -0.8(3) . . . . ?
C23 N2 C24 C7 178.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C23 H11 Br1 0.98 3.13 4.010(3) 150.2 1_554
C21 H15 O1 0.95 2.57 3.440(3) 151.7 3_566
N1 H5 O1 0.88 1.96 2.820(2) 166.5 3_567
C23 H11 Br1 0.98 3.13 4.010(3) 150.2 1_554
C21 H15 O1 0.95 2.57 3.440(3) 151.7 3_566
N1 H5 O1 0.88 1.96 2.820(2) 166.5 3_567
C23 H11 Br1 0.98 3.13 4.010(3) 150.2 1_554
C21 H15 O1 0.95 2.57 3.440(3) 151.7 3_566
N1 H5 O1 0.88 1.96 2.820(2) 166.5 3_567
C23 H11 Br1 0.98 3.13 4.010(3) 150.2 1_554
C21 H15 O1 0.95 2.57 3.440(3) 151.7 3_566
N1 H5 O1 0.88 1.96 2.820(2) 166.5 3_567
C21 H15 O1 0.95 2.57 3.440(3) 151.7 3_566
N1 H5 O1 0.88 1.96 2.820(2) 166.5 3_567
C21 H15 O1 0.95 2.57 3.440(3) 151.7 3_566
N1 H5 O1 0.88 1.96 2.820(2) 166.5 3_567
N1 H5 O1 0.88 1.96 2.820(2) 166.5 3_567
C21 H15 O1 0.95 2.57 3.440(3) 151.7 3_566
N1 H5 O1 0.88 1.96 2.820(2) 166.5 3_567
C21 H15 O1 0.95 2.57 3.440(3) 151.7 3_566
N1 H5 O1 0.88 1.96 2.820(2) 166.5 3_567
C21 H15 O1 0.95 2.57 3.440(3) 151.7 3_566
N1 H5 O1 0.88 1.96 2.820(2) 166.5 3_567
C21 H15 O1 0.95 2.57 3.440(3) 151.7 3_566
C23 H11 Br1 0.98 3.13 4.010(3) 150.2 1_554

_refine_diff_density_max         0.792
_refine_diff_density_min         -0.734
_refine_diff_density_rms         0.083



####################################################################### 
# 
# 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_gd_lxl39_0m
_database_code_depnum_ccdc_archive 'CCDC 1832339'
_audit_update_record             
;
2018-11-04 deposited with the CCDC.
2018-12-05 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.9966(15)
_cell_length_b                   15.5319(17)
_cell_length_c                   10.5220(12)
_cell_angle_alpha                90
_cell_angle_beta                 113.397(2)
_cell_angle_gamma                90
_cell_volume                     1949.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2300
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      25.30

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   0.2836
_exptl_transmission_factor_max   0.5264
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15650
_diffrn_reflns_av_unetI/netI     0.1887
_diffrn_reflns_av_R_equivalents  0.1013
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.153
_diffrn_reflns_theta_max         28.268
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measured_fraction_theta_full 0.825
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_Laue_measured_fraction_full 0.825
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_point_group_measured_fraction_full 0.825
_reflns_number_total             4173
_reflns_number_gt                1962
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0596P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4173
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1316
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1615
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   0.835
_refine_ls_restrained_S_all      0.835
_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 0.42864(8) -0.15430(6) 1.05159(9) 0.0381(3) Uani 1 1 d . . . . .
O1 O 0.05981(17) -0.06068(13) 0.3947(2) 0.0207(5) Uani 1 1 d . . . . .
N1 N 0.1651(2) 0.02396(17) 0.0277(2) 0.0218(6) Uani 1 1 d . . . . .
N2 N 0.1292(2) 0.05620(16) 0.5364(3) 0.0203(6) Uani 1 1 d . . . . .
H14 H 0.0791 0.0588 0.5730 0.024 Uiso 1 1 calc R U . . .
C1 C 0.3960(3) -0.1298(2) 0.8775(3) 0.0246(7) Uani 1 1 d . . . . .
C2 C 0.4615(3) -0.0726(2) 0.8447(3) 0.0252(7) Uani 1 1 d . . . . .
H19 H 0.5243 -0.0464 0.9154 0.030 Uiso 1 1 calc R U . . .
C3 C 0.4352(3) -0.0534(2) 0.7067(3) 0.0238(7) Uani 1 1 d . . . . .
H2 H 0.4809 -0.0140 0.6836 0.029 Uiso 1 1 calc R U . . .
C4 C 0.3434(2) -0.0906(2) 0.6011(3) 0.0195(6) Uani 1 1 d . . . . .
C5 C 0.3094(2) -0.0673(2) 0.4505(3) 0.0211(7) Uani 1 1 d . . . . .
H6 H 0.2703 -0.1170 0.3925 0.025 Uiso 1 1 calc R U . . .
H5 H 0.3777 -0.0558 0.4333 0.025 Uiso 1 1 calc R U . . .
C6 C 0.2314(2) 0.01288(19) 0.4061(3) 0.0182(6) Uani 1 1 d . . . . .
C7 C 0.1919(3) 0.0314(2) 0.2519(3) 0.0216(7) Uani 1 1 d . . . . .
C8 C 0.1142(2) 0.0985(2) 0.1788(3) 0.0217(7) Uani 1 1 d . . . . .
C9 C 0.1002(3) 0.0907(2) 0.0381(3) 0.0226(7) Uani 1 1 d . . . . .
C10 C 0.0278(3) 0.1448(2) -0.0656(3) 0.0280(7) Uani 1 1 d . . . . .
H11 H 0.0175 0.1384 -0.1597 0.034 Uiso 1 1 calc R U . . .
C11 C -0.0275(3) 0.2075(2) -0.0250(3) 0.0302(8) Uani 1 1 d . . . . .
H1 H -0.0756 0.2461 -0.0925 0.036 Uiso 1 1 calc R U . . .
C12 C 0.2809(3) -0.1495(2) 0.6389(3) 0.0258(7) Uani 1 1 d . . . . .
H4 H 0.2191 -0.1769 0.5684 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3053(3) -0.1699(2) 0.7763(3) 0.0268(7) Uani 1 1 d . . . . .
H3 H 0.2610 -0.2102 0.8002 0.032 Uiso 1 1 calc R U . . .
C14 C 0.1753(3) -0.0044(3) -0.0970(3) 0.0346(9) Uani 1 1 d . . . . .
H7 H 0.1012 -0.0048 -0.1735 0.052 Uiso 1 1 calc R U . . .
H9 H 0.2070 -0.0626 -0.0833 0.052 Uiso 1 1 calc R U . . .
H8 H 0.2249 0.0349 -0.1191 0.052 Uiso 1 1 calc R U . . .
C15 C 0.2187(3) -0.0112(2) 0.1589(3) 0.0253(7) Uani 1 1 d . . . . .
H10 H 0.2681 -0.0591 0.1799 0.030 Uiso 1 1 calc R U . . .
C16 C -0.0154(3) 0.2162(2) 0.1125(3) 0.0302(8) Uani 1 1 d . . . . .
H12 H -0.0564 0.2595 0.1361 0.036 Uiso 1 1 calc R U . . .
C17 C 0.0546(3) 0.1633(2) 0.2133(3) 0.0266(7) Uani 1 1 d . . . . .
H13 H 0.0630 0.1703 0.3066 0.032 Uiso 1 1 calc R U . . .
C18 C 0.2826(2) 0.0916(2) 0.4935(3) 0.0210(7) Uani 1 1 d . . . . .
C19 C 0.2207(2) 0.1142(2) 0.5682(3) 0.0204(6) Uani 1 1 d . . . . .
C20 C 0.1289(2) -0.00337(19) 0.4428(3) 0.0176(6) Uani 1 1 d . . . . .
C21 C 0.2463(3) 0.1848(2) 0.6563(4) 0.0300(8) Uani 1 1 d . . . . .
H18 H 0.2022 0.1999 0.7064 0.036 Uiso 1 1 calc R U . . .
C22 C 0.3403(3) 0.2322(2) 0.6672(4) 0.0351(9) Uani 1 1 d . . . . .
H17 H 0.3612 0.2806 0.7272 0.042 Uiso 1 1 calc R U . . .
C23 C 0.4034(3) 0.2113(2) 0.5945(4) 0.0376(9) Uani 1 1 d . . . . .
H16 H 0.4668 0.2455 0.6047 0.045 Uiso 1 1 calc R U . . .
C24 C 0.3763(3) 0.1403(2) 0.5051(3) 0.0288(8) Uani 1 1 d . . . . .
H15 H 0.4200 0.1258 0.4541 0.035 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 C1 1.749(3) . ?
O1 C20 1.222(3) . ?
N1 C9 1.368(4) . ?
N1 C15 1.387(4) . ?
N1 C14 1.440(4) . ?
N2 C20 1.350(4) . ?
N2 C19 1.423(4) . ?
N2 H14 0.8800 . ?
C1 C2 1.368(5) . ?
C1 C13 1.383(5) . ?
C2 C3 1.385(4) . ?
C2 H19 0.9500 . ?
C3 C4 1.392(4) . ?
C3 H2 0.9500 . ?
C4 C12 1.382(4) . ?
C4 C5 1.511(4) . ?
C5 C6 1.555(4) . ?
C5 H6 0.9900 . ?
C5 H5 0.9900 . ?
C6 C18 1.515(4) . ?
C6 C7 1.522(4) . ?
C6 C20 1.548(4) . ?
C7 C15 1.336(4) . ?
C7 C8 1.443(4) . ?
C8 C17 1.403(4) . ?
C8 C9 1.422(4) . ?
C9 C10 1.402(4) . ?
C10 C11 1.376(5) . ?
C10 H11 0.9500 . ?
C11 C16 1.398(5) . ?
C11 H1 0.9500 . ?
C12 C13 1.389(4) . ?
C12 H4 0.9500 . ?
C13 H3 0.9500 . ?
C14 H7 0.9800 . ?
C14 H9 0.9800 . ?
C14 H8 0.9800 . ?
C15 H10 0.9500 . ?
C16 C17 1.365(4) . ?
C16 H12 0.9500 . ?
C17 H13 0.9500 . ?
C18 C19 1.375(4) . ?
C18 C24 1.397(4) . ?
C19 C21 1.388(4) . ?
C21 C22 1.391(5) . ?
C21 H18 0.9500 . ?
C22 C23 1.363(5) . ?
C22 H17 0.9500 . ?
C23 C24 1.401(5) . ?
C23 H16 0.9500 . ?
C24 H15 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
C9 N1 C15 107.5(2) . . ?
C9 N1 C14 126.0(3) . . ?
C15 N1 C14 126.5(3) . . ?
C20 N2 C19 111.5(2) . . ?
C20 N2 H14 124.3 . . ?
C19 N2 H14 124.3 . . ?
C2 C1 C13 121.6(3) . . ?
C2 C1 Cl1 119.3(3) . . ?
C13 C1 Cl1 119.1(3) . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H19 120.5 . . ?
C3 C2 H19 120.5 . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 H2 119.2 . . ?
C4 C3 H2 119.2 . . ?
C12 C4 C3 117.4(3) . . ?
C12 C4 C5 120.0(3) . . ?
C3 C4 C5 122.6(3) . . ?
C4 C5 C6 113.0(2) . . ?
C4 C5 H6 109.0 . . ?
C6 C5 H6 109.0 . . ?
C4 C5 H5 109.0 . . ?
C6 C5 H5 109.0 . . ?
H6 C5 H5 107.8 . . ?
C18 C6 C7 112.1(2) . . ?
C18 C6 C20 101.2(2) . . ?
C7 C6 C20 109.7(2) . . ?
C18 C6 C5 112.7(2) . . ?
C7 C6 C5 112.0(2) . . ?
C20 C6 C5 108.5(2) . . ?
C15 C7 C8 107.3(3) . . ?
C15 C7 C6 127.7(3) . . ?
C8 C7 C6 125.0(3) . . ?
C17 C8 C9 118.3(3) . . ?
C17 C8 C7 136.2(3) . . ?
C9 C8 C7 105.5(3) . . ?
N1 C9 C10 129.5(3) . . ?
N1 C9 C8 108.6(3) . . ?
C10 C9 C8 121.9(3) . . ?
C11 C10 C9 117.0(3) . . ?
C11 C10 H11 121.5 . . ?
C9 C10 H11 121.5 . . ?
C10 C11 C16 122.1(3) . . ?
C10 C11 H1 118.9 . . ?
C16 C11 H1 118.9 . . ?
C4 C12 C13 122.2(3) . . ?
C4 C12 H4 118.9 . . ?
C13 C12 H4 118.9 . . ?
C1 C13 C12 118.2(3) . . ?
C1 C13 H3 120.9 . . ?
C12 C13 H3 120.9 . . ?
N1 C14 H7 109.5 . . ?
N1 C14 H9 109.5 . . ?
H7 C14 H9 109.5 . . ?
N1 C14 H8 109.5 . . ?
H7 C14 H8 109.5 . . ?
H9 C14 H8 109.5 . . ?
C7 C15 N1 111.1(3) . . ?
C7 C15 H10 124.5 . . ?
N1 C15 H10 124.5 . . ?
C17 C16 C11 120.8(3) . . ?
C17 C16 H12 119.6 . . ?
C11 C16 H12 119.6 . . ?
C16 C17 C8 119.8(3) . . ?
C16 C17 H13 120.1 . . ?
C8 C17 H13 120.1 . . ?
C19 C18 C24 119.9(3) . . ?
C19 C18 C6 109.7(3) . . ?
C24 C18 C6 130.3(3) . . ?
C18 C19 C21 123.0(3) . . ?
C18 C19 N2 109.1(3) . . ?
C21 C19 N2 127.9(3) . . ?
O1 C20 N2 126.2(3) . . ?
O1 C20 C6 125.4(3) . . ?
N2 C20 C6 108.5(2) . . ?
C19 C21 C22 116.2(3) . . ?
C19 C21 H18 121.9 . . ?
C22 C21 H18 121.9 . . ?
C23 C22 C21 122.2(3) . . ?
C23 C22 H17 118.9 . . ?
C21 C22 H17 118.9 . . ?
C22 C23 C24 121.1(3) . . ?
C22 C23 H16 119.4 . . ?
C24 C23 H16 119.4 . . ?
C18 C24 C23 117.6(3) . . ?
C18 C24 H15 121.2 . . ?
C23 C24 H15 121.2 . . ?

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
C13 C1 C2 C3 1.1(5) . . . . ?
Cl1 C1 C2 C3 -180.0(2) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C3 C4 C12 -1.8(5) . . . . ?
C2 C3 C4 C5 176.7(3) . . . . ?
C12 C4 C5 C6 92.4(3) . . . . ?
C3 C4 C5 C6 -86.1(3) . . . . ?
C4 C5 C6 C18 56.4(3) . . . . ?
C4 C5 C6 C7 -176.1(3) . . . . ?
C4 C5 C6 C20 -54.8(3) . . . . ?
C18 C6 C7 C15 126.2(3) . . . . ?
C20 C6 C7 C15 -122.2(3) . . . . ?
C5 C6 C7 C15 -1.6(5) . . . . ?
C18 C6 C7 C8 -55.6(4) . . . . ?
C20 C6 C7 C8 56.0(4) . . . . ?
C5 C6 C7 C8 176.5(3) . . . . ?
C15 C7 C8 C17 179.1(4) . . . . ?
C6 C7 C8 C17 0.7(6) . . . . ?
C15 C7 C8 C9 -0.4(4) . . . . ?
C6 C7 C8 C9 -178.8(3) . . . . ?
C15 N1 C9 C10 -178.0(3) . . . . ?
C14 N1 C9 C10 1.9(5) . . . . ?
C15 N1 C9 C8 0.7(4) . . . . ?
C14 N1 C9 C8 -179.4(3) . . . . ?
C17 C8 C9 N1 -179.8(3) . . . . ?
C7 C8 C9 N1 -0.2(3) . . . . ?
C17 C8 C9 C10 -1.0(5) . . . . ?
C7 C8 C9 C10 178.6(3) . . . . ?
N1 C9 C10 C11 -179.9(3) . . . . ?
C8 C9 C10 C11 1.5(5) . . . . ?
C9 C10 C11 C16 -1.7(5) . . . . ?
C3 C4 C12 C13 1.8(5) . . . . ?
C5 C4 C12 C13 -176.8(3) . . . . ?
C2 C1 C13 C12 -1.0(5) . . . . ?
Cl1 C1 C13 C12 180.0(2) . . . . ?
C4 C12 C13 C1 -0.5(5) . . . . ?
C8 C7 C15 N1 0.8(4) . . . . ?
C6 C7 C15 N1 179.2(3) . . . . ?
C9 N1 C15 C7 -1.0(4) . . . . ?
C14 N1 C15 C7 179.1(3) . . . . ?
C10 C11 C16 C17 1.4(6) . . . . ?
C11 C16 C17 C8 -0.9(5) . . . . ?
C9 C8 C17 C16 0.6(5) . . . . ?
C7 C8 C17 C16 -178.8(3) . . . . ?
C7 C6 C18 C19 117.9(3) . . . . ?
C20 C6 C18 C19 1.0(3) . . . . ?
C5 C6 C18 C19 -114.6(3) . . . . ?
C7 C6 C18 C24 -61.3(4) . . . . ?
C20 C6 C18 C24 -178.1(3) . . . . ?
C5 C6 C18 C24 66.2(4) . . . . ?
C24 C18 C19 C21 0.3(5) . . . . ?
C6 C18 C19 C21 -179.0(3) . . . . ?
C24 C18 C19 N2 178.7(3) . . . . ?
C6 C18 C19 N2 -0.5(3) . . . . ?
C20 N2 C19 C18 -0.3(3) . . . . ?
C20 N2 C19 C21 178.0(3) . . . . ?
C19 N2 C20 O1 -179.0(3) . . . . ?
C19 N2 C20 C6 1.0(3) . . . . ?
C18 C6 C20 O1 178.8(3) . . . . ?
C7 C6 C20 O1 60.3(4) . . . . ?
C5 C6 C20 O1 -62.4(3) . . . . ?
C18 C6 C20 N2 -1.2(3) . . . . ?
C7 C6 C20 N2 -119.8(3) . . . . ?
C5 C6 C20 N2 117.6(3) . . . . ?
C18 C19 C21 C22 -0.7(5) . . . . ?
N2 C19 C21 C22 -178.8(3) . . . . ?
C19 C21 C22 C23 0.7(5) . . . . ?
C21 C22 C23 C24 -0.2(6) . . . . ?
C19 C18 C24 C23 0.2(5) . . . . ?
C6 C18 C24 C23 179.3(3) . . . . ?
C22 C23 C24 C18 -0.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H7 O1 0.98 2.64 3.546(4) 154.0 3
C10 H11 O1 0.95 2.57 3.445(4) 153.0 3
N2 H14 O1 0.88 1.96 2.825(3) 165.3 3_556
C10 H11 O1 0.95 2.57 3.445(4) 153.0 3
N2 H14 O1 0.88 1.96 2.825(3) 165.3 3_556
N2 H14 O1 0.88 1.96 2.825(3) 165.3 3_556
C10 H11 O1 0.95 2.57 3.445(4) 153.0 3
C14 H7 O1 0.98 2.64 3.546(4) 154.0 3
N2 H14 O1 0.88 1.96 2.825(3) 165.3 3_556
C10 H11 O1 0.95 2.57 3.445(4) 153.0 3
C14 H7 O1 0.98 2.64 3.546(4) 154.0 3
N2 H14 O1 0.88 1.96 2.825(3) 165.3 3_556
C10 H11 O1 0.95 2.57 3.445(4) 153.0 3
C14 H7 O1 0.98 2.64 3.546(4) 154.0 3

_refine_diff_density_max         0.413
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.067



####################################################################### 
# 
# 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_gd_lxl38_0m
_database_code_depnum_ccdc_archive 'CCDC 1844831'
_audit_update_record             
;
2018-11-04 deposited with the CCDC.
2018-12-05 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         'C16 H14 Cl N O2'
_chemical_formula_sum            'C16 H14 Cl N O2'
_chemical_formula_weight         287.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.5976(9)
_cell_length_b                   10.3316(9)
_cell_length_c                   13.9249(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1380.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      31.02

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   0.2986
_exptl_transmission_factor_max   0.3374
_exptl_crystal_size_max          0.740
_exptl_crystal_size_mid          0.650
_exptl_crystal_size_min          0.580
_exptl_absorpt_coefficient_mu    0.277
_shelx_estimated_absorpt_T_min   0.821
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15337
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.455
_diffrn_reflns_theta_max         31.018
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4126
_reflns_number_gt                4016
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     0.905
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0451P)²+0.1692P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 1671 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.055(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4126
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0713
_refine_ls_wR_factor_gt          0.0706
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 0.24227(4) 0.75717(4) 0.12632(2) 0.02750(9) Uani 1 1 d . . . . .
O1 O 0.03730(10) 0.58848(10) 0.43736(7) 0.01959(19) Uani 1 1 d . . . . .
O2 O 0.20383(11) 0.79237(10) 0.52558(7) 0.0221(2) Uani 1 1 d . . . . .
N1 N 0.38113(11) 0.69546(11) 0.43784(8) 0.0180(2) Uani 1 1 d . . . . .
H11 H 0.4539 0.7355 0.4622 0.022 Uiso 1 1 calc R U . . .
C1 C 0.48441(14) 0.43299(14) 0.26756(10) 0.0197(2) Uani 1 1 d . . . . .
H1 H 0.5628 0.3891 0.2416 0.024 Uiso 1 1 calc R U . . .
C2 C 0.35148(14) 0.39462(13) 0.23998(10) 0.0195(2) Uani 1 1 d . . . . .
H14 H 0.3400 0.3248 0.1963 0.023 Uiso 1 1 calc R U . . .
C3 C 0.23473(14) 0.45868(12) 0.27651(9) 0.0173(2) Uani 1 1 d . . . . .
H13 H 0.1435 0.4336 0.2576 0.021 Uiso 1 1 calc R U . . .
C4 C 0.25426(13) 0.55931(11) 0.34072(8) 0.0143(2) Uani 1 1 d . . . . .
C5 C 0.15131(12) 0.64721(12) 0.39022(9) 0.0145(2) Uani 1 1 d . . . . .
C6 C 0.08852(12) 0.74944(13) 0.32170(8) 0.0160(2) Uani 1 1 d . . . . .
H10 H 0.0203 0.8025 0.3576 0.019 Uiso 1 1 calc R U . . .
H9 H 0.1638 0.8077 0.2994 0.019 Uiso 1 1 calc R U . . .
C7 C 0.01742(13) 0.69118(12) 0.23557(9) 0.0150(2) Uani 1 1 d . . . . .
C8 C -0.11570(14) 0.63714(14) 0.24442(10) 0.0190(2) Uani 1 1 d . . . . .
H8 H -0.1605 0.6373 0.3052 0.023 Uiso 1 1 calc R U . . .
C9 C -0.18341(15) 0.58336(14) 0.16583(11) 0.0236(3) Uani 1 1 d . . . . .
H7 H -0.2744 0.5485 0.1732 0.028 Uiso 1 1 calc R U . . .
C10 C -0.11897(16) 0.58028(14) 0.07665(11) 0.0239(3) Uani 1 1 d . . . . .
H2 H -0.1649 0.5417 0.0234 0.029 Uiso 1 1 calc R U . . .
C11 C 0.07493(16) 0.48154(15) 0.49799(10) 0.0240(3) Uani 1 1 d . . . . .
H4 H 0.1107 0.4105 0.4584 0.036 Uiso 1 1 calc R U . . .
H5 H -0.0073 0.4521 0.5335 0.036 Uiso 1 1 calc R U . . .
H3 H 0.1471 0.5091 0.5434 0.036 Uiso 1 1 calc R U . . .
C12 C 0.01261(16) 0.63369(13) 0.06543(10) 0.0225(3) Uani 1 1 d . . . . .
H6 H 0.0573 0.6326 0.0046 0.027 Uiso 1 1 calc R U . . .
C13 C 0.07823(13) 0.68895(13) 0.14463(9) 0.0174(2) Uani 1 1 d . . . . .
C14 C 0.24623(13) 0.72154(12) 0.46165(8) 0.0165(2) Uani 1 1 d . . . . .
C15 C 0.38855(13) 0.59534(12) 0.36867(9) 0.0151(2) Uani 1 1 d . . . . .
C16 C 0.50604(13) 0.53456(14) 0.33267(9) 0.0185(2) Uani 1 1 d . . . . .
H12 H 0.5971 0.5605 0.3512 0.022 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 C13 1.7437(13) . ?
O1 C5 1.4129(15) . ?
O1 C11 1.4366(17) . ?
O2 C14 1.2221(15) . ?
N1 C14 1.3634(16) . ?
N1 C15 1.4152(16) . ?
N1 H11 0.8800 . ?
C1 C2 1.3901(19) . ?
C1 C16 1.4023(19) . ?
C1 H1 0.9500 . ?
C2 C3 1.3973(18) . ?
C2 H14 0.9500 . ?
C3 C4 1.3840(16) . ?
C3 H13 0.9500 . ?
C4 C15 1.3968(16) . ?
C4 C5 1.5087(17) . ?
C5 C6 1.5457(17) . ?
C5 C14 1.5521(17) . ?
C6 C7 1.5054(17) . ?
C6 H10 0.9900 . ?
C6 H9 0.9900 . ?
C7 C13 1.3946(17) . ?
C7 C8 1.3997(18) . ?
C8 C9 1.3888(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(2) . ?
C9 H7 0.9500 . ?
C10 C12 1.387(2) . ?
C10 H2 0.9500 . ?
C11 H4 0.9800 . ?
C11 H5 0.9800 . ?
C11 H3 0.9800 . ?
C12 C13 1.3925(18) . ?
C12 H6 0.9500 . ?
C15 C16 1.3847(17) . ?
C16 H12 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
C5 O1 C11 114.12(10) . . ?
C14 N1 C15 110.96(10) . . ?
C14 N1 H11 124.5 . . ?
C15 N1 H11 124.5 . . ?
C2 C1 C16 121.87(12) . . ?
C2 C1 H1 119.1 . . ?
C16 C1 H1 119.1 . . ?
C1 C2 C3 120.02(12) . . ?
C1 C2 H14 120.0 . . ?
C3 C2 H14 120.0 . . ?
C4 C3 C2 118.84(12) . . ?
C4 C3 H13 120.6 . . ?
C2 C3 H13 120.6 . . ?
C3 C4 C15 120.35(11) . . ?
C3 C4 C5 131.20(11) . . ?
C15 C4 C5 108.45(10) . . ?
O1 C5 C4 117.45(10) . . ?
O1 C5 C6 106.16(10) . . ?
C4 C5 C6 112.62(10) . . ?
O1 C5 C14 111.68(10) . . ?
C4 C5 C14 101.90(9) . . ?
C6 C5 C14 106.64(10) . . ?
C7 C6 C5 113.28(10) . . ?
C7 C6 H10 108.9 . . ?
C5 C6 H10 108.9 . . ?
C7 C6 H9 108.9 . . ?
C5 C6 H9 108.9 . . ?
H10 C6 H9 107.7 . . ?
C13 C7 C8 117.09(12) . . ?
C13 C7 C6 122.70(11) . . ?
C8 C7 C6 120.21(11) . . ?
C9 C8 C7 121.16(13) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 120.38(13) . . ?
C10 C9 H7 119.8 . . ?
C8 C9 H7 119.8 . . ?
C12 C10 C9 119.84(13) . . ?
C12 C10 H2 120.1 . . ?
C9 C10 H2 120.1 . . ?
O1 C11 H4 109.5 . . ?
O1 C11 H5 109.5 . . ?
H4 C11 H5 109.5 . . ?
O1 C11 H3 109.5 . . ?
H4 C11 H3 109.5 . . ?
H5 C11 H3 109.5 . . ?
C10 C12 C13 119.05(13) . . ?
C10 C12 H6 120.5 . . ?
C13 C12 H6 120.5 . . ?
C12 C13 C7 122.46(12) . . ?
C12 C13 Cl1 117.28(10) . . ?
C7 C13 Cl1 120.26(10) . . ?
O2 C14 N1 127.71(12) . . ?
O2 C14 C5 124.58(12) . . ?
N1 C14 C5 107.69(10) . . ?
C16 C15 C4 121.98(12) . . ?
C16 C15 N1 128.23(11) . . ?
C4 C15 N1 109.76(10) . . ?
C15 C16 C1 116.93(11) . . ?
C15 C16 H12 121.5 . . ?
C1 C16 H12 121.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C1 C2 C3 0.7(2) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 C15 -0.34(18) . . . . ?
C2 C3 C4 C5 178.63(12) . . . . ?
C11 O1 C5 C4 47.48(15) . . . . ?
C11 O1 C5 C6 174.48(10) . . . . ?
C11 O1 C5 C14 -69.68(14) . . . . ?
C3 C4 C5 O1 49.81(18) . . . . ?
C15 C4 C5 O1 -131.13(11) . . . . ?
C3 C4 C5 C6 -73.98(17) . . . . ?
C15 C4 C5 C6 105.08(12) . . . . ?
C3 C4 C5 C14 172.14(13) . . . . ?
C15 C4 C5 C14 -8.80(12) . . . . ?
O1 C5 C6 C7 -72.68(12) . . . . ?
C4 C5 C6 C7 57.16(13) . . . . ?
C14 C5 C6 C7 168.12(10) . . . . ?
C5 C6 C7 C13 -102.90(14) . . . . ?
C5 C6 C7 C8 77.64(14) . . . . ?
C13 C7 C8 C9 0.25(19) . . . . ?
C6 C7 C8 C9 179.74(12) . . . . ?
C7 C8 C9 C10 1.0(2) . . . . ?
C8 C9 C10 C12 -1.4(2) . . . . ?
C9 C10 C12 C13 0.4(2) . . . . ?
C10 C12 C13 C7 0.9(2) . . . . ?
C10 C12 C13 Cl1 -178.95(11) . . . . ?
C8 C7 C13 C12 -1.23(19) . . . . ?
C6 C7 C13 C12 179.30(12) . . . . ?
C8 C7 C13 Cl1 178.62(10) . . . . ?
C6 C7 C13 Cl1 -0.85(18) . . . . ?
C15 N1 C14 O2 171.89(12) . . . . ?
C15 N1 C14 C5 -9.72(14) . . . . ?
O1 C5 C14 O2 -44.17(16) . . . . ?
C4 C5 C14 O2 -170.38(12) . . . . ?
C6 C5 C14 O2 71.38(15) . . . . ?
O1 C5 C14 N1 137.37(11) . . . . ?
C4 C5 C14 N1 11.17(13) . . . . ?
C6 C5 C14 N1 -107.08(11) . . . . ?
C3 C4 C15 C16 1.16(19) . . . . ?
C5 C4 C15 C16 -178.02(12) . . . . ?
C3 C4 C15 N1 -177.12(11) . . . . ?
C5 C4 C15 N1 3.70(14) . . . . ?
C14 N1 C15 C16 -174.13(13) . . . . ?
C14 N1 C15 C4 4.02(15) . . . . ?
C4 C15 C16 C1 -1.01(19) . . . . ?
N1 C15 C16 C1 176.92(12) . . . . ?
C2 C1 C16 C15 0.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C16 H12 O2 0.95 2.51 3.2707(17) 137.0 2_566
C6 H9 Cl1 0.99 2.58 3.0960(13) 112.5 .
N1 H11 O2 0.88 2.42 3.1413(15) 139.2 2_566
N1 H11 O1 0.88 2.43 3.2014(15) 146.7 2_566
C16 H12 O2 0.95 2.51 3.2707(17) 137.0 2_566
C6 H9 Cl1 0.99 2.58 3.0960(13) 112.5 .
N1 H11 O2 0.88 2.42 3.1413(15) 139.2 2_566
N1 H11 O1 0.88 2.43 3.2014(15) 146.7 2_566
C16 H12 O2 0.95 2.51 3.2707(17) 137.0 2_566
C6 H9 Cl1 0.99 2.58 3.0960(13) 112.5 .
N1 H11 O2 0.88 2.42 3.1413(15) 139.2 2_566
N1 H11 O1 0.88 2.43 3.2014(15) 146.7 2_566
C16 H12 O2 0.95 2.51 3.2707(17) 137.0 2_566
C6 H9 Cl1 0.99 2.58 3.0960(13) 112.5 .
N1 H11 O2 0.88 2.42 3.1413(15) 139.2 2_566
N1 H11 O1 0.88 2.43 3.2014(15) 146.7 2_566
C16 H12 O2 0.95 2.51 3.2707(17) 137.0 2_566
C6 H9 Cl1 0.99 2.58 3.0960(13) 112.5 .
N1 H11 O2 0.88 2.42 3.1413(15) 139.2 2_566
N1 H11 O1 0.88 2.43 3.2014(15) 146.7 2_566
N1 H11 O1 0.88 2.43 3.2014(15) 146.7 2_566
N1 H11 O2 0.88 2.42 3.1413(15) 139.2 2_566
C6 H9 Cl1 0.99 2.58 3.0960(13) 112.5 .
C16 H12 O2 0.95 2.51 3.2707(17) 137.0 2_566
N1 H11 O1 0.88 2.43 3.2014(15) 146.7 2_566
N1 H11 O2 0.88 2.42 3.1413(15) 139.2 2_566
C6 H9 Cl1 0.99 2.58 3.0960(13) 112.5 .
C16 H12 O2 0.95 2.51 3.2707(17) 137.0 2_566
N1 H11 O1 0.88 2.43 3.2014(15) 146.7 2_566
N1 H11 O2 0.88 2.42 3.1413(15) 139.2 2_566
C6 H9 Cl1 0.99 2.58 3.0960(13) 112.5 .
C16 H12 O2 0.95 2.51 3.2707(17) 137.0 2_566
N1 H11 O1 0.88 2.43 3.2014(15) 146.7 2_566
N1 H11 O2 0.88 2.42 3.1413(15) 139.2 2_566
C6 H9 Cl1 0.99 2.58 3.0960(13) 112.5 .
C16 H12 O2 0.95 2.51 3.2707(17) 137.0 2_566
N1 H11 O1 0.88 2.43 3.2014(15) 146.7 2_566
N1 H11 O2 0.88 2.42 3.1413(15) 139.2 2_566
C6 H9 Cl1 0.99 2.58 3.0960(13) 112.5 .
C16 H12 O2 0.95 2.51 3.2707(17) 137.0 2_566
N1 H11 O1 0.88 2.43 3.2014(15) 146.7 2_566
N1 H11 O2 0.88 2.42 3.1413(15) 139.2 2_566
C6 H9 Cl1 0.99 2.58 3.0960(13) 112.5 .
C16 H12 O2 0.95 2.51 3.2707(17) 137.0 2_566
N1 H11 O1 0.88 2.43 3.2014(15) 146.7 2_566
N1 H11 O2 0.88 2.42 3.1413(15) 139.2 2_566
C6 H9 Cl1 0.99 2.58 3.0960(13) 112.5 .
C16 H12 O2 0.95 2.51 3.2707(17) 137.0 2_566

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.045



####################################################################### 
# 
# 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_71
_database_code_depnum_ccdc_archive 'CCDC 1832340'
_audit_update_record             
;
2018-11-04 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;
_audit_creation_date             2018-01-22
_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         'C19 H16 N2 O'
_chemical_formula_sum            'C19 H16 N2 O'
_chemical_formula_weight         288.34
_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'
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                   8.8020(5)
_cell_length_b                   9.9463(7)
_cell_length_c                   10.2130(8)
_cell_angle_alpha                116.522(7)
_cell_angle_beta                 100.853(6)
_cell_angle_gamma                103.243(5)
_cell_volume                     734.13(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3261
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.8350
_cell_measurement_theta_min      2.4580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7205
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.488
_diffrn_reflns_theta_min         2.364
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  40.00   1.00    1.50    --   11.74 -57.00 150.00  100
  2  ω    -21.00  88.00   1.00    1.50    --   11.74  77.00  60.00  109
  3  ω    -16.00  85.00   1.00    1.50    --   11.74  57.00 -60.00  101
  4  ω     34.00  86.00   1.00    1.50    --   11.74-178.00 150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0666393000
_diffrn_orient_matrix_UB_12      -0.0634942000
_diffrn_orient_matrix_UB_13      -0.0667980000
_diffrn_orient_matrix_UB_21      -0.0511593000
_diffrn_orient_matrix_UB_22      0.0467735000
_diffrn_orient_matrix_UB_23      0.0174270000
_diffrn_orient_matrix_UB_31      0.0255692000
_diffrn_orient_matrix_UB_32      0.0325105000
_diffrn_orient_matrix_UB_33      -0.0448745000
_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                2774
_reflns_number_total             3407
_reflns_odcompleteness_completeness 100.00
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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         0.283
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.050
_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         3407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0480
_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)+(0.0544P)²+0.2120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1230
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C17(H17), C2(H2A), C19(H19), C15(H15), C5(H5), C14(H14),
 C4(H4), C3(H3), C11(H11), C18(H18), C13(H13), C12(H12)
;
_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 0.18307(12) -0.03405(12) 0.57654(12) 0.0218(3) Uani 1 1 d . . . . .
N1 N 0.46792(15) 0.06723(14) 0.66762(14) 0.0192(3) Uani 1 1 d . . . . .
H1 H 0.484411 -0.011523 0.674824 0.023 Uiso 1 1 calc R . . . .
N2 N 0.11534(15) 0.09888(14) 0.35487(14) 0.0198(3) Uani 1 1 d . . . . .
H2 H 0.037065 0.069160 0.386281 0.024 Uiso 1 1 calc R . . . .
C16 C 0.27879(17) 0.18283(16) 0.44490(17) 0.0172(3) Uani 1 1 d . . . . .
C6 C 0.59590(18) 0.20861(17) 0.70890(16) 0.0183(3) Uani 1 1 d . . . . .
C7 C 0.31560(17) 0.07000(17) 0.61518(16) 0.0173(3) Uani 1 1 d . . . . .
C10 C 0.26193(17) 0.48403(17) 0.73658(17) 0.0191(3) Uani 1 1 d . . . . .
C17 C 0.36431(18) 0.20701(17) 0.35257(17) 0.0192(3) Uani 1 1 d . . . . .
H17 H 0.477428 0.260949 0.383275 0.023 Uiso 1 1 calc R . . . .
C8 C 0.33941(17) 0.22877(16) 0.61337(16) 0.0169(3) Uani 1 1 d . . . . .
C1 C 0.52603(17) 0.31121(17) 0.68297(16) 0.0183(3) Uani 1 1 d . . . . .
C2 C 0.62893(18) 0.45917(18) 0.71762(17) 0.0221(3) Uani 1 1 d . . . . .
H2A H 0.584853 0.528700 0.700466 0.026 Uiso 1 1 calc R . . . .
C19 C 0.09575(19) 0.06958(18) 0.20718(17) 0.0224(3) Uani 1 1 d . . . . .
H19 H -0.003595 0.015133 0.124800 0.027 Uiso 1 1 calc R . . . .
C15 C 0.20081(17) 0.50782(18) 0.61486(18) 0.0204(3) Uani 1 1 d . . . . .
H15 H 0.151503 0.420303 0.513998 0.024 Uiso 1 1 calc R . . . .
C5 C 0.76474(18) 0.24839(19) 0.76865(17) 0.0219(3) Uani 1 1 d . . . . .
H5 H 0.808587 0.178407 0.785109 0.026 Uiso 1 1 calc R . . . .
C14 C 0.21305(18) 0.66117(18) 0.64320(18) 0.0219(3) Uani 1 1 d . . . . .
H14 H 0.172063 0.675483 0.561378 0.026 Uiso 1 1 calc R . . . .
C9 C 0.24110(18) 0.31773(17) 0.71065(17) 0.0191(3) Uani 1 1 d . . . . .
H9A H 0.124419 0.251876 0.659477 0.023 Uiso 1 1 calc R . . . .
H9B H 0.274234 0.326657 0.811170 0.023 Uiso 1 1 calc R . . . .
C4 C 0.86624(18) 0.39790(19) 0.80310(17) 0.0240(3) Uani 1 1 d . . . . .
H4 H 0.980482 0.428431 0.843151 0.029 Uiso 1 1 calc R . . . .
C3 C 0.80019(19) 0.50256(19) 0.77882(18) 0.0252(4) Uani 1 1 d . . . . .
H3 H 0.870489 0.602135 0.803485 0.030 Uiso 1 1 calc R . . . .
C11 C 0.33684(19) 0.61755(18) 0.88618(18) 0.0238(3) Uani 1 1 d . . . . .
H11 H 0.379304 0.604033 0.968180 0.029 Uiso 1 1 calc R . . . .
C18 C 0.24773(19) 0.13432(18) 0.20199(18) 0.0228(3) Uani 1 1 d . . . . .
H18 H 0.270520 0.131269 0.115610 0.027 Uiso 1 1 calc R . . . .
C13 C 0.28621(19) 0.79251(18) 0.79310(19) 0.0235(3) Uani 1 1 d . . . . .
H13 H 0.293166 0.894690 0.812130 0.028 Uiso 1 1 calc R . . . .
C12 C 0.3491(2) 0.77091(19) 0.91486(19) 0.0270(4) Uani 1 1 d . . . . .
H12 H 0.399380 0.858874 1.015413 0.032 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
O1 C7 1.2233(17) . ?
N1 H1 0.8600 . ?
N1 C6 1.4107(18) . ?
N1 C7 1.3582(18) . ?
N2 H2 0.8600 . ?
N2 C16 1.3706(18) . ?
N2 C19 1.3697(19) . ?
C16 C17 1.379(2) . ?
C16 C8 1.515(2) . ?
C6 C1 1.399(2) . ?
C6 C5 1.382(2) . ?
C7 C8 1.5537(19) . ?
C10 C15 1.400(2) . ?
C10 C9 1.5137(19) . ?
C10 C11 1.393(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.419(2) . ?
C8 C1 1.5161(19) . ?
C8 C9 1.552(2) . ?
C1 C2 1.384(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.398(2) . ?
C19 H19 0.9300 . ?
C19 C18 1.367(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.393(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.392(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.386(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C3 1.392(2) . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.392(2) . ?
C18 H18 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.390(2) . ?
C12 H12 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
C6 N1 H1 123.9 . . ?
C7 N1 H1 123.9 . . ?
C7 N1 C6 112.12(12) . . ?
C16 N2 H2 125.2 . . ?
C16 N2 C19 109.57(12) . . ?
C19 N2 H2 125.2 . . ?
N2 C16 C17 107.61(13) . . ?
N2 C16 C8 121.70(12) . . ?
C17 C16 C8 130.66(13) . . ?
C1 C6 N1 109.06(12) . . ?
C5 C6 N1 128.05(13) . . ?
C5 C6 C1 122.88(13) . . ?
O1 C7 N1 125.99(13) . . ?
O1 C7 C8 126.06(12) . . ?
N1 C7 C8 107.95(11) . . ?
C15 C10 C9 121.82(13) . . ?
C11 C10 C15 118.38(13) . . ?
C11 C10 C9 119.73(13) . . ?
C16 C17 H17 126.4 . . ?
C16 C17 C18 107.30(13) . . ?
C18 C17 H17 126.4 . . ?
C16 C8 C7 107.03(11) . . ?
C16 C8 C1 111.01(12) . . ?
C16 C8 C9 113.37(11) . . ?
C7 C8 C9 107.69(11) . . ?
C1 C8 C7 101.65(11) . . ?
C1 C8 C9 115.05(12) . . ?
C6 C1 C8 109.07(12) . . ?
C2 C1 C6 119.24(13) . . ?
C2 C1 C8 131.67(13) . . ?
C1 C2 H2A 120.5 . . ?
C1 C2 C3 118.99(14) . . ?
C3 C2 H2A 120.5 . . ?
N2 C19 H19 126.0 . . ?
C18 C19 N2 108.09(13) . . ?
C18 C19 H19 126.0 . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.71(14) . . ?
C14 C15 H15 119.6 . . ?
C6 C5 H5 121.5 . . ?
C6 C5 C4 117.04(14) . . ?
C4 C5 H5 121.5 . . ?
C15 C14 H14 119.9 . . ?
C13 C14 C15 120.15(14) . . ?
C13 C14 H14 119.9 . . ?
C10 C9 C8 115.99(12) . . ?
C10 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
C8 C9 H9A 108.3 . . ?
C8 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C5 C4 H4 119.3 . . ?
C5 C4 C3 121.33(14) . . ?
C3 C4 H4 119.3 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.51(14) . . ?
C4 C3 H3 119.7 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.03(14) . . ?
C12 C11 H11 119.5 . . ?
C17 C18 H18 126.3 . . ?
C19 C18 C17 107.44(13) . . ?
C19 C18 H18 126.3 . . ?
C14 C13 H13 120.1 . . ?
C14 C13 C12 119.76(14) . . ?
C12 C13 H13 120.1 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.96(15) . . ?
C13 C12 H12 120.0 . . ?


_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.641
_oxdiff_exptl_absorpt_empirical_full_min 0.578
####################################################################### 
# 
# 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_gd_lxl40_0m
_database_code_depnum_ccdc_archive 'CCDC 1844832'
_audit_update_record             
;
2018-11-04 deposited with the CCDC.
2018-12-05 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         'C19 H19 Cl2 N O4'
_chemical_formula_sum            'C19 H19 Cl2 N O4'
_chemical_formula_weight         396.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   33.580(5)
_cell_length_b                   13.960(2)
_cell_length_c                   8.0737(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.506(3)
_cell_angle_gamma                90
_cell_volume                     3721.4(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6225
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.50

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   0.3773
_exptl_transmission_factor_max   0.4334
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    0.373
_shelx_estimated_absorpt_T_min   0.780
_shelx_estimated_absorpt_T_max   0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19010
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_av_R_equivalents  0.1026
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.233
_diffrn_reflns_theta_max         28.569
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4742
_reflns_number_gt                3518
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1235P)²+24.7188P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4742
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0945
_refine_ls_wR_factor_ref         0.2749
_refine_ls_wR_factor_gt          0.2570
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001

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 0.22742(4) 1.09687(8) 1.03869(16) 0.0440(3) Uani 1 1 d . . . . .
Cl2 Cl 0.20602(3) 0.72545(7) 1.15884(16) 0.0422(3) Uani 1 1 d . . . . .
C102 C 0.11339(13) 0.7641(3) 1.0455(6) 0.0339(9) Uani 1 1 d . . . . .
H10A H 0.0904 0.7890 1.0943 0.041 Uiso 1 1 calc R U . . .
H10B H 0.1271 0.7141 1.1224 0.041 Uiso 1 1 calc R U . . .
O2 O 0.07155(10) 0.7875(2) 0.7783(4) 0.0402(8) Uani 1 1 d . . . . .
O3 O 0.04112(11) 0.6291(3) 0.9704(5) 0.0518(9) Uani 1 1 d . . . . .
C103 C 0.07604(18) 0.4517(3) 0.8769(7) 0.0484(12) Uani 1 1 d . . . . .
H10C H 0.0519 0.4526 0.9291 0.073 Uiso 1 1 calc R U . . .
H10D H 0.0971 0.4126 0.9453 0.073 Uiso 1 1 calc R U . . .
H10E H 0.0691 0.4243 0.7635 0.073 Uiso 1 1 calc R U . . .
O20 O 0.0618(2) 0.8788(6) 0.3502(9) 0.122(3) Uani 1 1 d . . . . .
H20 H 0.0428 0.8682 0.2691 0.183 Uiso 1 1 calc R U . . .
C1 C 0.19498(13) 0.9992(3) 1.0305(5) 0.0306(8) Uani 1 1 d . . . . .
C2 C 0.15391(13) 1.0123(3) 0.9753(6) 0.0348(9) Uani 1 1 d . . . . .
H11 H 0.1434 1.0729 0.9357 0.042 Uiso 1 1 calc R U . . .
C3 C 0.12878(12) 0.9350(3) 0.9792(6) 0.0340(9) Uani 1 1 d . . . . .
H1 H 0.1005 0.9434 0.9410 0.041 Uiso 1 1 calc R U . . .
C4 C 0.14294(12) 0.8449(3) 1.0369(5) 0.0298(8) Uani 1 1 d . . . . .
C5 C 0.09657(12) 0.7179(3) 0.8731(5) 0.0308(8) Uani 1 1 d . . . . .
C6 C 0.0503(2) 0.7508(5) 0.6214(9) 0.078(2) Uani 1 1 d . . . . .
H2 H 0.0345 0.6934 0.6416 0.094 Uiso 1 1 calc R U . . .
H5 H 0.0698 0.7320 0.5490 0.094 Uiso 1 1 calc R U . . .
C7 C 0.0222(3) 0.8270(6) 0.5350(11) 0.084(2) Uani 1 1 d . . . . .
H3 H 0.0085 0.8564 0.6226 0.101 Uiso 1 1 calc R U . . .
C8 C 0.0471(3) 0.9000(7) 0.4814(11) 0.098(3) Uani 1 1 d . . . . .
H8A H 0.0309 0.9593 0.4583 0.117 Uiso 1 1 calc R U . . .
H8B H 0.0698 0.9138 0.5751 0.117 Uiso 1 1 calc R U . . .
O19 O -0.0073(2) 0.7881(6) 0.4158(11) 0.147(4) Uani 1 1 d . . . . .
H19 H -0.0201 0.7467 0.4606 0.221 Uiso 1 1 calc R U . . .
C10 C 0.07198(13) 0.6288(3) 0.9099(6) 0.0376(10) Uani 1 1 d . . . . .
N10 N 0.09098(11) 0.5494(3) 0.8659(5) 0.0362(8) Uani 1 1 d . . . . .
C12 C 0.12489(12) 0.5745(3) 0.7940(5) 0.0299(8) Uani 1 1 d . . . . .
C13 C 0.12860(12) 0.6740(3) 0.7888(5) 0.0289(8) Uani 1 1 d . . . . .
C14 C 0.15821(13) 0.7145(3) 0.7160(6) 0.0339(9) Uani 1 1 d . . . . .
H9 H 0.1607 0.7821 0.7111 0.041 Uiso 1 1 calc R U . . .
C15 C 0.18471(14) 0.6550(3) 0.6488(6) 0.0381(9) Uani 1 1 d . . . . .
H8 H 0.2050 0.6824 0.5955 0.046 Uiso 1 1 calc R U . . .
C16 C 0.18156(13) 0.5560(3) 0.6597(6) 0.0398(10) Uani 1 1 d . . . . .
H7 H 0.2003 0.5165 0.6163 0.048 Uiso 1 1 calc R U . . .
C17 C 0.15147(13) 0.5137(3) 0.7331(5) 0.0355(9) Uani 1 1 d . . . . .
H6 H 0.1493 0.4461 0.7411 0.043 Uiso 1 1 calc R U . . .
C18 C 0.18441(12) 0.8351(3) 1.0877(5) 0.0287(8) Uani 1 1 d . . . . .
C19 C 0.21114(12) 0.9114(3) 1.0845(5) 0.0328(9) Uani 1 1 d . . . . .
H10 H 0.2395 0.9031 1.1184 0.039 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 C1 1.739(4) . ?
Cl2 C18 1.746(4) . ?
C102 C4 1.512(6) . ?
C102 C5 1.545(6) . ?
C102 H10A 0.9900 . ?
C102 H10B 0.9900 . ?
O2 C5 1.415(5) . ?
O2 C6 1.432(7) . ?
O3 C10 1.223(6) . ?
C103 N10 1.462(5) . ?
C103 H10C 0.9800 . ?
C103 H10D 0.9800 . ?
C103 H10E 0.9800 . ?
O20 C8 1.281(10) . ?
O20 H20 0.8400 . ?
C1 C19 1.379(6) . ?
C1 C2 1.382(6) . ?
C2 C3 1.373(6) . ?
C2 H11 0.9500 . ?
C3 C4 1.396(5) . ?
C3 H1 0.9500 . ?
C4 C18 1.385(5) . ?
C5 C13 1.504(6) . ?
C5 C10 1.552(6) . ?
C6 C7 1.505(9) . ?
C6 H2 0.9900 . ?
C6 H5 0.9900 . ?
C7 O19 1.363(10) . ?
C7 C8 1.435(11) . ?
C7 H3 1.0000 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
O19 H19 0.8400 . ?
C10 N10 1.358(6) . ?
N10 C12 1.413(6) . ?
C12 C17 1.385(6) . ?
C12 C13 1.396(5) . ?
C13 C14 1.366(6) . ?
C14 C15 1.396(6) . ?
C14 H9 0.9500 . ?
C15 C16 1.390(7) . ?
C15 H8 0.9500 . ?
C16 C17 1.393(7) . ?
C16 H7 0.9500 . ?
C17 H6 0.9500 . ?
C18 C19 1.397(6) . ?
C19 H10 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
C4 C102 C5 113.9(4) . . ?
C4 C102 H10A 108.8 . . ?
C5 C102 H10A 108.8 . . ?
C4 C102 H10B 108.8 . . ?
C5 C102 H10B 108.8 . . ?
H10A C102 H10B 107.7 . . ?
C5 O2 C6 112.6(4) . . ?
N10 C103 H10C 109.5 . . ?
N10 C103 H10D 109.5 . . ?
H10C C103 H10D 109.5 . . ?
N10 C103 H10E 109.5 . . ?
H10C C103 H10E 109.5 . . ?
H10D C103 H10E 109.5 . . ?
C8 O20 H20 109.5 . . ?
C19 C1 C2 122.1(4) . . ?
C19 C1 Cl1 118.5(3) . . ?
C2 C1 Cl1 119.4(3) . . ?
C3 C2 C1 118.1(4) . . ?
C3 C2 H11 121.0 . . ?
C1 C2 H11 121.0 . . ?
C2 C3 C4 122.9(4) . . ?
C2 C3 H1 118.6 . . ?
C4 C3 H1 118.6 . . ?
C18 C4 C3 116.8(4) . . ?
C18 C4 C102 123.1(4) . . ?
C3 C4 C102 120.1(4) . . ?
O2 C5 C13 116.0(4) . . ?
O2 C5 C102 106.5(3) . . ?
C13 C5 C102 113.8(3) . . ?
O2 C5 C10 111.7(3) . . ?
C13 C5 C10 102.1(3) . . ?
C102 C5 C10 106.4(4) . . ?
O2 C6 C7 109.0(5) . . ?
O2 C6 H2 109.9 . . ?
C7 C6 H2 109.9 . . ?
O2 C6 H5 109.9 . . ?
C7 C6 H5 109.9 . . ?
H2 C6 H5 108.3 . . ?
O19 C7 C8 117.4(7) . . ?
O19 C7 C6 111.0(7) . . ?
C8 C7 C6 106.9(8) . . ?
O19 C7 H3 107.0 . . ?
C8 C7 H3 107.0 . . ?
C6 C7 H3 107.0 . . ?
O20 C8 C7 114.8(8) . . ?
O20 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
O20 C8 H8B 108.6 . . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C7 O19 H19 109.5 . . ?
O3 C10 N10 125.5(4) . . ?
O3 C10 C5 126.4(4) . . ?
N10 C10 C5 108.2(4) . . ?
C10 N10 C12 111.0(3) . . ?
C10 N10 C103 124.2(4) . . ?
C12 N10 C103 124.5(4) . . ?
C17 C12 C13 122.2(4) . . ?
C17 C12 N10 127.9(4) . . ?
C13 C12 N10 110.0(4) . . ?
C14 C13 C12 120.0(4) . . ?
C14 C13 C5 131.5(4) . . ?
C12 C13 C5 108.5(4) . . ?
C13 C14 C15 119.1(4) . . ?
C13 C14 H9 120.4 . . ?
C15 C14 H9 120.4 . . ?
C16 C15 C14 120.3(4) . . ?
C16 C15 H8 119.8 . . ?
C14 C15 H8 119.8 . . ?
C15 C16 C17 121.2(4) . . ?
C15 C16 H7 119.4 . . ?
C17 C16 H7 119.4 . . ?
C12 C17 C16 117.1(4) . . ?
C12 C17 H6 121.4 . . ?
C16 C17 H6 121.4 . . ?
C4 C18 C19 122.3(4) . . ?
C4 C18 Cl2 121.3(3) . . ?
C19 C18 Cl2 116.4(3) . . ?
C1 C19 C18 117.8(4) . . ?
C1 C19 H10 121.1 . . ?
C18 C19 H10 121.1 . . ?

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
C19 C1 C2 C3 1.6(7) . . . . ?
Cl1 C1 C2 C3 -176.3(3) . . . . ?
C1 C2 C3 C4 0.3(7) . . . . ?
C2 C3 C4 C18 -1.5(7) . . . . ?
C2 C3 C4 C102 177.1(4) . . . . ?
C5 C102 C4 C18 -104.2(4) . . . . ?
C5 C102 C4 C3 77.3(5) . . . . ?
C6 O2 C5 C13 58.7(6) . . . . ?
C6 O2 C5 C102 -173.5(5) . . . . ?
C6 O2 C5 C10 -57.8(6) . . . . ?
C4 C102 C5 O2 -68.4(4) . . . . ?
C4 C102 C5 C13 60.6(5) . . . . ?
C4 C102 C5 C10 172.3(3) . . . . ?
C5 O2 C6 C7 175.9(6) . . . . ?
O2 C6 C7 O19 -160.7(8) . . . . ?
O2 C6 C7 C8 70.1(9) . . . . ?
O19 C7 C8 O20 -49.1(14) . . . . ?
C6 C7 C8 O20 76.4(11) . . . . ?
O2 C5 C10 O3 -51.2(6) . . . . ?
C13 C5 C10 O3 -175.8(4) . . . . ?
C102 C5 C10 O3 64.6(6) . . . . ?
O2 C5 C10 N10 129.8(4) . . . . ?
C13 C5 C10 N10 5.1(4) . . . . ?
C102 C5 C10 N10 -114.4(4) . . . . ?
O3 C10 N10 C12 177.8(4) . . . . ?
C5 C10 N10 C12 -3.2(5) . . . . ?
O3 C10 N10 C103 3.2(7) . . . . ?
C5 C10 N10 C103 -177.8(4) . . . . ?
C10 N10 C12 C17 -179.6(4) . . . . ?
C103 N10 C12 C17 -5.0(6) . . . . ?
C10 N10 C12 C13 -0.3(5) . . . . ?
C103 N10 C12 C13 174.2(4) . . . . ?
C17 C12 C13 C14 2.6(6) . . . . ?
N10 C12 C13 C14 -176.6(4) . . . . ?
C17 C12 C13 C5 -176.9(3) . . . . ?
N10 C12 C13 C5 3.8(4) . . . . ?
O2 C5 C13 C14 53.5(6) . . . . ?
C102 C5 C13 C14 -70.6(5) . . . . ?
C10 C5 C13 C14 175.2(4) . . . . ?
O2 C5 C13 C12 -127.1(4) . . . . ?
C102 C5 C13 C12 108.9(4) . . . . ?
C10 C5 C13 C12 -5.3(4) . . . . ?
C12 C13 C14 C15 -0.6(6) . . . . ?
C5 C13 C14 C15 178.8(4) . . . . ?
C13 C14 C15 C16 -1.5(6) . . . . ?
C14 C15 C16 C17 1.8(6) . . . . ?
C13 C12 C17 C16 -2.4(6) . . . . ?
N10 C12 C17 C16 176.7(4) . . . . ?
C15 C16 C17 C12 0.2(6) . . . . ?
C3 C4 C18 C19 0.9(6) . . . . ?
C102 C4 C18 C19 -177.7(4) . . . . ?
C3 C4 C18 Cl2 -178.8(3) . . . . ?
C102 C4 C18 Cl2 2.6(6) . . . . ?
C2 C1 C19 C18 -2.2(6) . . . . ?
Cl1 C1 C19 C18 175.8(3) . . . . ?
C4 C18 C19 C1 0.9(6) . . . . ?
Cl2 C18 C19 C1 -179.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O19 H19 O3 0.84 1.91 2.727(8) 164.2 2_556
O20 H20 O19 0.84 2.06 2.851(9) 156.4 2
C103 H10E O3 0.98 2.50 3.466(7) 170.5 6_565
C102 H10B Cl2 0.99 2.62 3.125(4) 111.8 .
C102 H10B Cl2 0.99 2.62 3.125(4) 111.8 .
C103 H10E O3 0.98 2.50 3.466(7) 170.5 6_565
O20 H20 O19 0.84 2.06 2.851(9) 156.4 2
O19 H19 O3 0.84 1.91 2.727(8) 164.2 2_556

_refine_diff_density_max         1.801
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.118



