# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_bir16_01
_database_code_depnum_ccdc_archive 'CCDC 1568018'
_audit_update_record             
;
2017-08-09 deposited with the CCDC.
2017-10-26 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT041_bir16_01            
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: The molecule was crystallized from a solvent mixture that 
          co-crystallized in the same interstitial site.  The solvent 
          mixture was deuterated chloroform and dichloromethane.
;
_vrf_PLAT077_bir16_01            
;
PROBLEM: Unitcell contains non-integer number of atoms ..     Please Check
RESPONSE: The molecule was crystallized from a solvent mixture that 
          co-crystallized in the same interstitial site.  The solvent 
          mixture was deuterated chloroform and dichloromethane.
;
_vrf_PLAT250_bir16_01            
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.9 Note  
RESPONSE: The unique chlorine atom (Cl7) of the dichloromethane interstitial 
          solvent had a larger thermal ellipsoid than the chlorine atom that 
          overlapped with one of the chlorine atoms of the deuterated 
          chloroform molecule.
;
# end Validation Reply Form

_audit_creation_date             2016-02-16T13:00:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C15 H10.25 Cl5.88 D0.88 N O3'
_chemical_formula_weight         462.52

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5591(9)
_cell_length_b                   13.2129(11)
_cell_length_c                   12.0726(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.8840(10)
_cell_angle_gamma                90
_cell_volume                     1843.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9825
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.92

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       chip
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_F_000             928

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6721
_shelx_estimated_absorpt_T_min   0.755
_shelx_estimated_absorpt_T_max   0.946

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_number            22244
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.762
_diffrn_reflns_theta_max         27.942
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             4409
_reflns_number_gt                3893
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_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-2014/7 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+1.0754P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4409
_refine_ls_number_parameters     240
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0731
_refine_ls_wR_factor_gt          0.0699
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.059

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
D D 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.83177(3) -0.04356(3) 0.54881(3) 0.02169(10) Uani 1 d . .
Cl2 Cl 0.61565(4) -0.08007(3) 0.43122(4) 0.02687(10) Uani 1 d . .
Cl3 Cl 0.82533(4) -0.04793(3) 0.31090(3) 0.03235(12) Uani 1 d . .
O1 O 0.51175(9) 0.59603(7) 0.64921(8) 0.0152(2) Uani 1 d . .
O2 O 0.37681(9) 0.55275(8) 0.76597(9) 0.0185(2) Uani 1 d . .
O3 O 0.73501(10) 0.15008(8) 0.34177(9) 0.0195(2) Uani 1 d . .
N1 N 0.67592(10) 0.13971(9) 0.52007(10) 0.0125(2) Uani 1 d . .
H1 H 0.6653 0.0998 0.5773 0.015 Uiso 1 calc . .
C1 C 0.45518(13) 0.52341(11) 0.70835(12) 0.0142(3) Uani 1 d . .
C2 C 0.49122(13) 0.41858(11) 0.69629(12) 0.0146(3) Uani 1 d . .
C3 C 0.58267(12) 0.39352(10) 0.63121(11) 0.0130(3) Uani 1 d . .
C4 C 0.64783(13) 0.47389(10) 0.57744(11) 0.0137(3) Uani 1 d . .
C5 C 0.75141(13) 0.46050(11) 0.51962(13) 0.0179(3) Uani 1 d . .
H5 H 0.7823 0.3943 0.5116 0.021 Uiso 1 calc . .
C6 C 0.80896(14) 0.54165(12) 0.47437(14) 0.0228(3) Uani 1 d . .
H6 H 0.8791 0.5309 0.4361 0.027 Uiso 1 calc . .
C7 C 0.76484(15) 0.63944(12) 0.48440(14) 0.0231(3) Uani 1 d . .
H7 H 0.8038 0.6949 0.4515 0.028 Uiso 1 calc . .
C8 C 0.66435(14) 0.65546(11) 0.54220(13) 0.0191(3) Uani 1 d . .
H8 H 0.6339 0.7218 0.55 0.023 Uiso 1 calc . .
C9 C 0.60867(12) 0.57325(11) 0.58870(12) 0.0141(3) Uani 1 d . .
C10 C 0.61580(12) 0.28638(10) 0.62110(12) 0.0145(3) Uani 1 d . .
H10 H 0.615 0.2458 0.6861 0.017 Uiso 1 calc . .
C11 C 0.64684(12) 0.24264(10) 0.52663(12) 0.0135(3) Uani 1 d . .
H11 H 0.6494 0.2826 0.4613 0.016 Uiso 1 calc . .
C12 C 0.72034(12) 0.10199(10) 0.42574(12) 0.0126(3) Uani 1 d . .
C13 C 0.74900(13) -0.01310(11) 0.42943(12) 0.0159(3) Uani 1 d . .
C14 C 0.42195(15) 0.34277(12) 0.75934(13) 0.0224(3) Uani 1 d . .
H14A H 0.4148 0.2803 0.716 0.034 Uiso 1 calc . .
H14B H 0.3447 0.3703 0.7731 0.034 Uiso 1 calc . .
H14C H 0.4609 0.3281 0.8302 0.034 Uiso 1 calc . .
Cl4 Cl 0.95374(3) 0.23695(3) 0.56017(3) 0.02244(10) Uani 1 d . .
Cl5 Cl 1.05081(10) 0.30483(8) 0.77012(10) 0.0371(2) Uani 0.876(2) d A 1
Cl6 Cl 0.88334(4) 0.14322(4) 0.76546(4) 0.02865(17) Uani 0.876(2) d A 1
C15 C 0.9279(2) 0.2537(3) 0.70255(19) 0.0212(6) Uani 0.876(2) d A 1
D15 D 0.8638 0.304 0.7093 0.025 Uiso 0.876(2) calc A 1
C16 C 0.9080(19) 0.269(3) 0.6954(12) 0.0212(6) Uani 0.124(2) d A 2
H16A H 0.8709 0.3367 0.6944 0.025 Uiso 0.124(2) calc A 2
H16B H 0.8507 0.2192 0.7213 0.025 Uiso 0.124(2) calc A 2
Cl7 Cl 1.0286(9) 0.2703(10) 0.7850(9) 0.087(4) Uani 0.124(2) d A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.7640(15) . ?
Cl2 C13 1.7778(16) . ?
Cl3 C13 1.7541(15) . ?
O1 C1 1.3685(17) . ?
O1 C9 1.3801(17) . ?
O2 C1 1.2141(18) . ?
O3 C12 1.2105(17) . ?
N1 C12 1.3517(18) . ?
N1 C11 1.4035(17) . ?
N1 H1 0.88 . ?
C1 C2 1.454(2) . ?
C2 C3 1.367(2) . ?
C2 C14 1.498(2) . ?
C3 C4 1.4600(19) . ?
C3 C10 1.4721(19) . ?
C4 C9 1.3959(19) . ?
C4 C5 1.406(2) . ?
C5 C6 1.379(2) . ?
C5 H5 0.95 . ?
C6 C7 1.395(2) . ?
C6 H6 0.95 . ?
C7 C8 1.381(2) . ?
C7 H7 0.95 . ?
C8 C9 1.386(2) . ?
C8 H8 0.95 . ?
C10 C11 1.333(2) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12 C13 1.557(2) . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
Cl4 C15 1.763(2) . ?
Cl4 C16 1.776(15) . ?
Cl5 C15 1.763(3) . ?
Cl6 C15 1.727(4) . ?
C15 D15 1 . ?
C16 Cl7 1.751(16) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?

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
C1 O1 C9 121.44(11) . . ?
C12 N1 C11 119.95(12) . . ?
C12 N1 H1 120 . . ?
C11 N1 H1 120 . . ?
O2 C1 O1 116.22(13) . . ?
O2 C1 C2 125.37(13) . . ?
O1 C1 C2 118.40(12) . . ?
C3 C2 C1 120.89(13) . . ?
C3 C2 C14 123.65(13) . . ?
C1 C2 C14 115.46(12) . . ?
C2 C3 C4 119.21(13) . . ?
C2 C3 C10 119.01(13) . . ?
C4 C3 C10 121.73(13) . . ?
C9 C4 C5 116.52(13) . . ?
C9 C4 C3 118.06(13) . . ?
C5 C4 C3 125.33(13) . . ?
C6 C5 C4 121.23(14) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 120.43(15) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 119.83(14) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 118.96(14) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
O1 C9 C8 115.42(12) . . ?
O1 C9 C4 121.59(13) . . ?
C8 C9 C4 122.98(14) . . ?
C11 C10 C3 124.18(13) . . ?
C11 C10 H10 117.9 . . ?
C3 C10 H10 117.9 . . ?
C10 C11 N1 122.43(13) . . ?
C10 C11 H11 118.8 . . ?
N1 C11 H11 118.8 . . ?
O3 C12 N1 124.89(13) . . ?
O3 C12 C13 120.28(13) . . ?
N1 C12 C13 114.80(12) . . ?
C12 C13 Cl3 110.02(10) . . ?
C12 C13 Cl1 111.02(10) . . ?
Cl3 C13 Cl1 109.47(8) . . ?
C12 C13 Cl2 107.60(10) . . ?
Cl3 C13 Cl2 109.05(8) . . ?
Cl1 C13 Cl2 109.63(8) . . ?
C2 C14 H14A 109.5 . . ?
C2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Cl6 C15 Cl5 111.35(13) . . ?
Cl6 C15 Cl4 112.27(18) . . ?
Cl5 C15 Cl4 110.58(18) . . ?
Cl6 C15 D15 107.5 . . ?
Cl5 C15 D15 107.5 . . ?
Cl4 C15 D15 107.5 . . ?
Cl7 C16 Cl4 109.0(12) . . ?
Cl7 C16 H16A 109.9 . . ?
Cl4 C16 H16A 109.9 . . ?
Cl7 C16 H16B 109.9 . . ?
Cl4 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?


# END of CIF
_chemical_formula_moiety         'C14 H9 N O3, 0.88(C D Cl3), 0.12(C H2 Cl2)'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: deuterated chloroform, dichloromethane'
