# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_C22H19NOBr2
_database_code_depnum_ccdc_archive 'CCDC 1568276'
_audit_update_record             
;
2017-08-10 deposited with the CCDC.
2017-11-19 downloaded from the CCDC.
;

_audit_creation_date             2017-08-08T15:57:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C22 H19 Br2 N O'
_chemical_formula_weight         473.2

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

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x + 1/2, y + 1/2, -z+1/2'
'-x, -y, -z'
x+1/2,-y+1/2,z+1/2

_cell_length_a                   9.8099(5)
_cell_length_b                   14.0372(7)
_cell_length_c                   14.7788(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.878(6)
_cell_angle_gamma                90
_cell_volume                     2034.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    20953
_cell_measurement_theta_min      2.4570
_cell_measurement_theta_max      26.0880

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

_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             944
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_colour            colorless


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

_exptl_absorpt_coefficient_mu    3.994
_exptl_absorpt_correction_T_min  0.59738
_exptl_absorpt_correction_T_max  1.00000
_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.
;

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

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_number            70535
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.475
_diffrn_reflns_theta_max         29.554
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_ful 1
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4186
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0035828000
_diffrn_orient_matrix_UB_12      0.0271917000
_diffrn_orient_matrix_UB_13      0.0403900000
_diffrn_orient_matrix_UB_21      0.0682906000
_diffrn_orient_matrix_UB_22      -0.0126949000
_diffrn_orient_matrix_UB_23      0.0110258000
_diffrn_orient_matrix_UB_31      0.0237101000
_diffrn_orient_matrix_UB_32      0.0407018000
_diffrn_orient_matrix_UB_33      -0.0235303000

_diffrn_measurement_method       'ω scans'
_reflns_number_total             5499
_reflns_number_gt                3667
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

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

_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)+(0.0351P)²+2.1756P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5499
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.092
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0

#----------------------------------------------------------------------------#
#                   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'
Br Br -0.2901 2.4595 '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
Br1 Br 0.68260(3) 0.41704(2) 0.13616(3) 0.06467(12) Uani 1 d . .
Br2 Br 0.22280(4) 0.42162(3) 0.19642(3) 0.07601(14) Uani 1 d . .
O1 O 0.4270(3) 0.29551(15) 0.04974(13) 0.0634(6) Uani 1 d . .
N1 N 0.4710(2) 0.20880(15) 0.17580(14) 0.0425(5) Uani 1 d . .
C1 C 0.4654(3) 0.6353(2) 0.1407(2) 0.0498(7) Uani 1 d . .
H1 H 0.4587 0.6282 0.0782 0.06 Uiso 1 calc . .
C2 C 0.5003(3) 0.7227(2) 0.1775(2) 0.0585(8) Uani 1 d . .
H2 H 0.5157 0.7743 0.1395 0.07 Uiso 1 calc . .
C3 C 0.5125(3) 0.7338(2) 0.2688(3) 0.0603(8) Uani 1 d . .
H3 H 0.5364 0.7928 0.2931 0.072 Uiso 1 calc . .
C4 C 0.4894(4) 0.6580(3) 0.3248(2) 0.0735(10) Uani 1 d . .
H4 H 0.4986 0.6653 0.3871 0.088 Uiso 1 calc . .
C5 C 0.4524(4) 0.5707(2) 0.2887(2) 0.0707(10) Uani 1 d . .
H5 H 0.4355 0.5197 0.3272 0.085 Uiso 1 calc . .
C6 C 0.4404(3) 0.55837(19) 0.19649(19) 0.0457(6) Uani 1 d . .
C7 C 0.4044(3) 0.4640(2) 0.15483(19) 0.0495(7) Uani 1 d . .
H7 H 0.4014 0.4708 0.0888 0.059 Uiso 1 calc . .
C8 C 0.4976(3) 0.3826(2) 0.17961(18) 0.0467(6) Uani 1 d . .
H8 H 0.4992 0.3721 0.2452 0.056 Uiso 1 calc . .
C9 C 0.4605(3) 0.2911(2) 0.12954(18) 0.0460(6) Uani 1 d . .
C10 C 0.4977(3) 0.20093(18) 0.27181(17) 0.0396(6) Uani 1 d . .
C11 C 0.3898(3) 0.2049(3) 0.3301(2) 0.0606(8) Uani 1 d . .
H11 H 0.3018 0.2152 0.3079 0.073 Uiso 1 calc . .
C12 C 0.4136(4) 0.1932(3) 0.4221(2) 0.0773(11) Uani 1 d . .
H12 H 0.3414 0.1964 0.462 0.093 Uiso 1 calc . .
C13 C 0.5429(4) 0.1772(3) 0.4544(2) 0.0725(10) Uani 1 d . .
H13 H 0.5581 0.1692 0.5162 0.087 Uiso 1 calc . .
C14 C 0.6498(4) 0.1727(3) 0.3963(2) 0.0679(9) Uani 1 d . .
H14 H 0.7376 0.1619 0.4186 0.081 Uiso 1 calc . .
C15 C 0.6272(3) 0.1841(2) 0.3039(2) 0.0528(7) Uani 1 d . .
H15 H 0.6996 0.1804 0.2641 0.063 Uiso 1 calc . .
C16 C 0.4441(3) 0.1187(2) 0.1269(2) 0.0505(7) Uani 1 d . .
H16A H 0.3872 0.1319 0.0741 0.061 Uiso 1 calc . .
H16B H 0.394 0.076 0.1658 0.061 Uiso 1 calc . .
C17 C 0.5724(3) 0.06988(19) 0.09710(18) 0.0463(6) Uani 1 d . .
C18 C 0.6135(4) -0.0147(2) 0.1354(2) 0.0617(8) Uani 1 d . .
H18 H 0.5627 -0.0413 0.1816 0.074 Uiso 1 calc . .
C19 C 0.7302(4) -0.0612(3) 0.1062(3) 0.0754(10) Uani 1 d . .
H19 H 0.7573 -0.1181 0.133 0.09 Uiso 1 calc . .
C20 C 0.8045(4) -0.0228(3) 0.0379(3) 0.0773(11) Uani 1 d . .
H20 H 0.8814 -0.0543 0.0172 0.093 Uiso 1 calc . .
C21 C 0.7657(4) 0.0618(3) 0.0000(3) 0.0776(11) Uani 1 d . .
H21 H 0.8174 0.0883 -0.0459 0.093 Uiso 1 calc . .
C22 C 0.6511(4) 0.1079(2) 0.0290(2) 0.0641(9) Uani 1 d . .
H22 H 0.6259 0.1655 0.0025 0.077 Uiso 1 calc . .



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

_geom_special_details            
;
 All esds 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.
;
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 C8 1.994(3) . ?
Br2 C7 1.984(3) . ?
O1 C9 1.221(3) . ?
N1 C9 1.346(3) . ?
N1 C10 1.443(3) . ?
N1 C16 1.479(3) . ?
C1 C6 1.382(4) . ?
C1 C2 1.383(4) . ?
C1 H1 0.93 . ?
C2 C3 1.363(5) . ?
C2 H2 0.93 . ?
C3 C4 1.369(5) . ?
C3 H3 0.93 . ?
C4 C5 1.383(5) . ?
C4 H4 0.93 . ?
C5 C6 1.377(4) . ?
C5 H5 0.93 . ?
C6 C7 1.501(4) . ?
C7 C8 1.506(4) . ?
C7 H7 0.98 . ?
C8 C9 1.523(4) . ?
C8 H8 0.98 . ?
C10 C15 1.370(4) . ?
C10 C11 1.376(4) . ?
C11 C12 1.386(5) . ?
C11 H11 0.93 . ?
C12 C13 1.366(5) . ?
C12 H12 0.93 . ?
C13 C14 1.367(5) . ?
C13 H13 0.93 . ?
C14 C15 1.389(4) . ?
C14 H14 0.93 . ?
C15 H15 0.93 . ?
C16 C17 1.505(4) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 C18 1.373(4) . ?
C17 C22 1.385(4) . ?
C18 C19 1.392(5) . ?
C18 H18 0.93 . ?
C19 C20 1.365(6) . ?
C19 H19 0.93 . ?
C20 C21 1.365(6) . ?
C20 H20 0.93 . ?
C21 C22 1.372(5) . ?
C21 H21 0.93 . ?
C22 H22 0.93 . ?

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 C10 125.2(2) . . ?
C9 N1 C16 118.3(2) . . ?
C10 N1 C16 116.4(2) . . ?
C6 C1 C2 120.3(3) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120 . . ?
C5 C4 H4 120 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 C7 122.2(3) . . ?
C1 C6 C7 119.2(3) . . ?
C6 C7 C8 115.6(2) . . ?
C6 C7 Br2 110.1(2) . . ?
C8 C7 Br2 104.02(19) . . ?
C6 C7 H7 109 . . ?
C8 C7 H7 109 . . ?
Br2 C7 H7 109 . . ?
C7 C8 C9 112.4(2) . . ?
C7 C8 Br1 106.87(19) . . ?
C9 C8 Br1 105.06(19) . . ?
C7 C8 H8 110.8 . . ?
C9 C8 H8 110.8 . . ?
Br1 C8 H8 110.8 . . ?
O1 C9 N1 123.4(3) . . ?
O1 C9 C8 119.1(2) . . ?
N1 C9 C8 117.5(2) . . ?
C15 C10 C11 120.6(3) . . ?
C15 C10 N1 120.5(2) . . ?
C11 C10 N1 118.8(3) . . ?
C10 C11 C12 119.3(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120 . . ?
C15 C14 H14 120 . . ?
C10 C15 C14 119.5(3) . . ?
C10 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
N1 C16 C17 112.9(2) . . ?
N1 C16 H16A 109 . . ?
C17 C16 H16A 109 . . ?
N1 C16 H16B 109 . . ?
C17 C16 H16B 109 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C22 118.0(3) . . ?
C18 C17 C16 121.0(3) . . ?
C22 C17 C16 121.0(3) . . ?
C17 C18 C19 121.0(3) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 119.7(4) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C21 C20 C19 119.9(4) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.4(4) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C17 121.0(3) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?

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
C6 C1 C2 C3 0.9(5) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C3 C4 C5 C6 1.0(6) . . . . ?
C4 C5 C6 C1 -0.3(6) . . . . ?
C4 C5 C6 C7 178.2(4) . . . . ?
C2 C1 C6 C5 -0.6(5) . . . . ?
C2 C1 C6 C7 -179.2(3) . . . . ?
C5 C6 C7 C8 -56.8(4) . . . . ?
C1 C6 C7 C8 121.8(3) . . . . ?
C5 C6 C7 Br2 60.7(4) . . . . ?
C1 C6 C7 Br2 -120.7(3) . . . . ?
C6 C7 C8 C9 -175.9(2) . . . . ?
Br2 C7 C8 C9 63.3(2) . . . . ?
C6 C7 C8 Br1 -61.1(3) . . . . ?
Br2 C7 C8 Br1 178.04(12) . . . . ?
C10 N1 C9 O1 -173.9(3) . . . . ?
C16 N1 C9 O1 1.7(4) . . . . ?
C10 N1 C9 C8 8.3(4) . . . . ?
C16 N1 C9 C8 -176.1(2) . . . . ?
C7 C8 C9 O1 40.7(4) . . . . ?
Br1 C8 C9 O1 -75.1(3) . . . . ?
C7 C8 C9 N1 -141.3(3) . . . . ?
Br1 C8 C9 N1 102.8(2) . . . . ?
C9 N1 C10 C15 -97.7(3) . . . . ?
C16 N1 C10 C15 86.6(3) . . . . ?
C9 N1 C10 C11 86.2(4) . . . . ?
C16 N1 C10 C11 -89.5(3) . . . . ?
C15 C10 C11 C12 1.1(5) . . . . ?
N1 C10 C11 C12 177.2(3) . . . . ?
C10 C11 C12 C13 -0.6(6) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C12 C13 C14 C15 -0.2(6) . . . . ?
C11 C10 C15 C14 -1.1(5) . . . . ?
N1 C10 C15 C14 -177.2(3) . . . . ?
C13 C14 C15 C10 0.7(5) . . . . ?
C9 N1 C16 C17 98.2(3) . . . . ?
C10 N1 C16 C17 -85.8(3) . . . . ?
N1 C16 C17 C18 111.4(3) . . . . ?
N1 C16 C17 C22 -69.9(3) . . . . ?
C22 C17 C18 C19 -0.5(5) . . . . ?
C16 C17 C18 C19 178.2(3) . . . . ?
C17 C18 C19 C20 -0.5(5) . . . . ?
C18 C19 C20 C21 1.3(6) . . . . ?
C19 C20 C21 C22 -1.1(6) . . . . ?
C20 C21 C22 C17 0.0(6) . . . . ?
C18 C17 C22 C21 0.8(5) . . . . ?
C16 C17 C22 C21 -177.9(3) . . . . ?

_refine_diff_density_max         0.829
_refine_diff_density_min         -0.898
_refine_diff_density_rms         0.057


