# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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. 
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data_lcs16002-comp1
_database_code_depnum_ccdc_archive 'CCDC 1523641'
_audit_update_record             
;
2016-12-20 deposited with the CCDC.
2018-04-24 downloaded from the CCDC.
;

# ========================================================================= #

_audit_creation_method           'SHELXL-2014/7 and enCIFer'
_shelx_SHELXL_version_number     2014/7
_audit_creation_date             '18 December 2016'

# ========================================================================= #

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H21 Mo N4 O4, C2 H3 N, Br'
_chemical_formula_sum            'C20 H24 Br Mo N5 O4'
_chemical_formula_weight         574.29

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mo Mo -1.6832 0.6857 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.5420(12)
_cell_length_b                   8.9322(12)
_cell_length_c                   17.705(3)
_cell_angle_alpha                87.812(7)
_cell_angle_beta                 88.701(8)
_cell_angle_gamma                87.216(7)
_cell_volume                     1190.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9235
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      24.78

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.264
_shelx_estimated_absorpt_T_min   0.840
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   
; 
'SADABS V2012/1 (Bruker AXS Inc.)' 
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40010
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.688
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994


_reflns_number_total             4843
_reflns_number_gt                4220
_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       'APEX2 (Bruker AXS Inc., 2012)'
_computing_cell_refinement       'SAINT (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2014)'


_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)+(0.0225P)²+0.8444P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4843
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0555
_refine_ls_wR_factor_gt          0.0529
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
Mo1 Mo 0.71836(2) 0.68767(2) 0.15877(2) 0.01999(6) Uani 1 1 d . . . . .
O1 O 0.6607(3) 0.4874(2) 0.30371(10) 0.0534(6) Uani 1 1 d . . . . .
O2 O 0.3699(3) 0.5477(2) 0.10116(13) 0.0546(5) Uani 1 1 d . . . . .
O3 O 0.8854(3) 0.40839(19) 0.07906(10) 0.0419(4) Uani 1 1 d . . . . .
O4 O 1.1069(3) 0.6952(3) 0.21984(11) 0.0515(5) Uani 1 1 d . . . . .
N1 N 0.7435(2) 0.8553(2) 0.06000(10) 0.0219(4) Uani 1 1 d . . . . .
N2 N 0.6244(2) 0.91618(18) 0.19804(9) 0.0190(4) Uani 1 1 d . . . . .
N3 N 0.5713(2) 0.97698(19) 0.26365(10) 0.0215(4) Uani 1 1 d . . . . .
N4 N 0.2219(2) 0.72329(19) 0.46064(10) 0.0220(4) Uani 1 1 d . . . . .
C1 C 0.8065(3) 0.8198(3) -0.00866(13) 0.0291(5) Uani 1 1 d . . . . .
H1 H 0.8428 0.7184 -0.0172 0.035 Uiso 1 1 calc R U . . .
C2 C 0.8206(3) 0.9248(3) -0.06748(13) 0.0343(6) Uani 1 1 d . . . . .
H2 H 0.8678 0.8961 -0.1153 0.041 Uiso 1 1 calc R U . . .
C3 C 0.7657(3) 1.0714(3) -0.05613(13) 0.0332(6) Uani 1 1 d . . . . .
H3 H 0.7731 1.1450 -0.0961 0.040 Uiso 1 1 calc R U . . .
C4 C 0.6997(3) 1.1103(3) 0.01393(13) 0.0270(5) Uani 1 1 d . . . . .
H4 H 0.6607 1.2109 0.0230 0.032 Uiso 1 1 calc R U . . .
C5 C 0.6911(3) 1.0002(2) 0.07111(12) 0.0203(4) Uani 1 1 d . . . . .
C6 C 0.6290(3) 1.0325(2) 0.14745(12) 0.0201(4) Uani 1 1 d . . . . .
C7 C 0.5763(3) 1.1664(2) 0.18144(13) 0.0271(5) Uani 1 1 d . . . . .
H7 H 0.5668 1.2640 0.1582 0.033 Uiso 1 1 calc R U . . .
C8 C 0.5413(3) 1.1268(2) 0.25540(13) 0.0273(5) Uani 1 1 d . . . . .
H8 H 0.5028 1.1928 0.2940 0.033 Uiso 1 1 calc R U . . .
C9 C 0.5606(3) 0.8861(2) 0.33363(12) 0.0237(5) Uani 1 1 d . . . . .
H9A H 0.5694 0.9515 0.3772 0.028 Uiso 1 1 calc R U . . .
H9B H 0.6622 0.8116 0.3353 0.028 Uiso 1 1 calc R U . . .
C10 C 0.3897(3) 0.8052(3) 0.34072(14) 0.0369(6) Uani 1 1 d . . . . .
H10A H 0.3771 0.7438 0.2959 0.044 Uiso 1 1 calc R U . . .
H10B H 0.2879 0.8793 0.3425 0.044 Uiso 1 1 calc R U . . .
C11 C 0.3878(3) 0.7039(3) 0.41249(14) 0.0354(6) Uani 1 1 d . . . . .
H11A H 0.4015 0.5980 0.3978 0.042 Uiso 1 1 calc R U . . .
H11B H 0.4914 0.7248 0.4431 0.042 Uiso 1 1 calc R U . . .
C12 C 0.1993(4) 0.8776(3) 0.48851(16) 0.0452(7) Uani 1 1 d . . . . .
H12A H 0.1810 0.9488 0.4456 0.068 Uiso 1 1 calc R U . . .
H12B H 0.3059 0.9018 0.5153 0.068 Uiso 1 1 calc R U . . .
H12C H 0.0961 0.8841 0.5231 0.068 Uiso 1 1 calc R U . . .
C13 C 0.2403(3) 0.6174(3) 0.52804(13) 0.0289(5) Uani 1 1 d . . . . .
H13A H 0.3448 0.6410 0.5564 0.043 Uiso 1 1 calc R U . . .
H13B H 0.2542 0.5142 0.5112 0.043 Uiso 1 1 calc R U . . .
H13C H 0.1339 0.6278 0.5606 0.043 Uiso 1 1 calc R U . . .
C14 C 0.0640(3) 0.6867(3) 0.41778(14) 0.0355(6) Uani 1 1 d . . . . .
H14A H -0.0413 0.6906 0.4512 0.053 Uiso 1 1 calc R U . . .
H14B H 0.0818 0.5857 0.3983 0.053 Uiso 1 1 calc R U . . .
H14C H 0.0472 0.7595 0.3754 0.053 Uiso 1 1 calc R U . . .
C15 C 0.6813(3) 0.5621(3) 0.24944(14) 0.0319(6) Uani 1 1 d . . . . .
C16 C 0.4855(3) 0.6123(3) 0.12160(14) 0.0309(5) Uani 1 1 d . . . . .
C17 C 0.8224(3) 0.5125(3) 0.10835(13) 0.0284(5) Uani 1 1 d . . . . .
C18 C 0.9669(3) 0.7074(3) 0.19722(13) 0.0287(5) Uani 1 1 d . . . . .
N5 N -0.0250(4) 0.0208(4) 0.30396(19) 0.0712(9) Uani 1 1 d . . . . .
C19 C 0.0532(5) 0.2867(3) 0.25594(17) 0.0537(8) Uani 1 1 d . . . . .
H19A H 0.0674 0.3501 0.2992 0.081 Uiso 1 1 calc R U . . .
H19B H -0.0422 0.3303 0.2241 0.081 Uiso 1 1 calc R U . . .
H19C H 0.1645 0.2807 0.2263 0.081 Uiso 1 1 calc R U . . .
C20 C 0.0088(4) 0.1374(4) 0.28290(17) 0.0473(7) Uani 1 1 d . . . . .
Br1 Br 0.29515(3) 0.25409(2) 0.42872(2) 0.02919(7) Uani 1 1 d . . . . .


_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
Mo1 C15 1.946(2) . ?
Mo1 C17 1.954(2) . ?
Mo1 C18 2.026(3) . ?
Mo1 C16 2.042(3) . ?
Mo1 N2 2.2576(17) . ?
Mo1 N1 2.2689(17) . ?
O1 C15 1.161(3) . ?
O2 C16 1.142(3) . ?
O3 C17 1.158(3) . ?
O4 C18 1.136(3) . ?
N1 C1 1.339(3) . ?
N1 C5 1.356(3) . ?
N2 N3 1.346(2) . ?
N2 C6 1.347(2) . ?
N3 C8 1.350(3) . ?
N3 C9 1.458(3) . ?
N4 C12 1.482(3) . ?
N4 C14 1.482(3) . ?
N4 C13 1.499(3) . ?
N4 C11 1.505(3) . ?
C1 C2 1.381(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.375(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.455(3) . ?
C6 C7 1.396(3) . ?
C7 C8 1.366(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.508(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.532(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N5 C20 1.131(4) . ?
C19 C20 1.452(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C15 Mo1 C17 89.13(10) . . ?
C15 Mo1 C18 85.46(10) . . ?
C17 Mo1 C18 84.50(10) . . ?
C15 Mo1 C16 86.81(10) . . ?
C17 Mo1 C16 83.43(10) . . ?
C18 Mo1 C16 165.75(9) . . ?
C15 Mo1 N2 101.82(8) . . ?
C17 Mo1 N2 168.57(8) . . ?
C18 Mo1 N2 93.00(8) . . ?
C16 Mo1 N2 100.30(8) . . ?
C15 Mo1 N1 173.41(8) . . ?
C17 Mo1 N1 97.40(8) . . ?
C18 Mo1 N1 95.96(8) . . ?
C16 Mo1 N1 93.09(8) . . ?
N2 Mo1 N1 71.71(6) . . ?
C1 N1 C5 117.97(18) . . ?
C1 N1 Mo1 124.03(14) . . ?
C5 N1 Mo1 117.99(13) . . ?
N3 N2 C6 105.13(16) . . ?
N3 N2 Mo1 136.99(13) . . ?
C6 N2 Mo1 117.71(13) . . ?
N2 N3 C8 111.58(17) . . ?
N2 N3 C9 121.35(17) . . ?
C8 N3 C9 126.98(18) . . ?
C12 N4 C14 110.13(19) . . ?
C12 N4 C13 107.80(18) . . ?
C14 N4 C13 109.22(17) . . ?
C12 N4 C11 111.51(19) . . ?
C14 N4 C11 110.44(19) . . ?
C13 N4 C11 107.65(16) . . ?
N1 C1 C2 122.5(2) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 119.3(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.2(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 122.1(2) . . ?
N1 C5 C6 115.34(17) . . ?
C4 C5 C6 122.5(2) . . ?
N2 C6 C7 110.66(18) . . ?
N2 C6 C5 117.22(18) . . ?
C7 C6 C5 132.08(19) . . ?
C8 C7 C6 105.14(19) . . ?
C8 C7 H7 127.4 . . ?
C6 C7 H7 127.4 . . ?
N3 C8 C7 107.49(19) . . ?
N3 C8 H8 126.3 . . ?
C7 C8 H8 126.3 . . ?
N3 C9 C10 112.06(18) . . ?
N3 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
N3 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 C11 110.6(2) . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N4 C11 C10 114.11(18) . . ?
N4 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
N4 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 Mo1 179.4(2) . . ?
O2 C16 Mo1 168.7(2) . . ?
O3 C17 Mo1 179.3(2) . . ?
O4 C18 Mo1 169.5(2) . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N5 C20 C19 179.7(3) . . ?

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 N2 N3 C8 0.6(2) . . . . ?
Mo1 N2 N3 C8 175.29(16) . . . . ?
C6 N2 N3 C9 -176.26(18) . . . . ?
Mo1 N2 N3 C9 -1.5(3) . . . . ?
C5 N1 C1 C2 0.5(3) . . . . ?
Mo1 N1 C1 C2 -179.75(18) . . . . ?
N1 C1 C2 C3 -1.1(4) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C1 N1 C5 C4 0.5(3) . . . . ?
Mo1 N1 C5 C4 -179.32(16) . . . . ?
C1 N1 C5 C6 -178.23(19) . . . . ?
Mo1 N1 C5 C6 2.0(2) . . . . ?
C3 C4 C5 N1 -0.8(3) . . . . ?
C3 C4 C5 C6 177.8(2) . . . . ?
N3 N2 C6 C7 -0.8(2) . . . . ?
Mo1 N2 C6 C7 -176.71(14) . . . . ?
N3 N2 C6 C5 177.13(18) . . . . ?
Mo1 N2 C6 C5 1.2(2) . . . . ?
N1 C5 C6 N2 -2.1(3) . . . . ?
C4 C5 C6 N2 179.2(2) . . . . ?
N1 C5 C6 C7 175.3(2) . . . . ?
C4 C5 C6 C7 -3.4(4) . . . . ?
N2 C6 C7 C8 0.7(3) . . . . ?
C5 C6 C7 C8 -176.8(2) . . . . ?
N2 N3 C8 C7 -0.1(3) . . . . ?
C9 N3 C8 C7 176.5(2) . . . . ?
C6 C7 C8 N3 -0.3(3) . . . . ?
N2 N3 C9 C10 -82.4(3) . . . . ?
C8 N3 C9 C10 101.3(3) . . . . ?
N3 C9 C10 C11 176.7(2) . . . . ?
C12 N4 C11 C10 -62.0(3) . . . . ?
C14 N4 C11 C10 60.8(3) . . . . ?
C13 N4 C11 C10 180.0(2) . . . . ?
C9 C10 C11 N4 130.1(2) . . . . ?

_refine_diff_density_max         0.776
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_lcs1915(comp1)
_database_code_depnum_ccdc_archive 'CCDC 1817124'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.
2018-04-24 downloaded from the CCDC.
;

# ========================================================================= #

_audit_creation_method           'SHELXL-2014/7 and enCIFer'
_shelx_SHELXL_version_number     2014/7
_audit_creation_date             '15 January 2018'

# ========================================================================= #


_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H21 Br Mo N4 O3, C2 H3 N'
_chemical_formula_sum            'C19 H24 Br Mo N5 O3'
_chemical_formula_weight         546.28

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'
Mo Mo -1.6832 0.6857 '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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.4060(6)
_cell_length_b                   9.7868(7)
_cell_length_c                   15.3808(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.385(4)
_cell_angle_gamma                90
_cell_volume                     1105.57(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7256
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      24.68

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.429
_shelx_estimated_absorpt_T_min   0.829
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_T_max  0.843
_exptl_absorpt_process_details   
; 
'SADABS V2012/1 (Bruker AXS Inc.)' 
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18898
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.843
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997


_reflns_number_total             5075
_reflns_number_gt                4280
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.998

_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       'APEX2 (Bruker AXS Inc., 2012)'
_computing_cell_refinement       'SAINT (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2014)'


_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.0972P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.029(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5075
_refine_ls_number_parameters     267
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.058
_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
Mo1 Mo 0.49408(7) 0.72130(4) 0.76804(3) 0.01751(14) Uani 1 1 d . . . . .
Br1 Br 0.68368(11) 0.50340(8) 0.84679(5) 0.0284(2) Uani 1 1 d . . . A 1
O1 O 0.2377(7) 0.7387(6) 0.9116(3) 0.0353(13) Uani 1 1 d . . . . .
N1 N 0.6686(7) 0.6856(5) 0.6574(3) 0.0158(12) Uani 1 1 d . . . . .
N2 N 0.3601(8) 0.5552(6) 0.6804(4) 0.0143(12) Uani 1 1 d . . . . .
O2 O 0.7091(9) 0.9547(6) 0.8738(4) 0.0474(17) Uani 1 1 d . . . . .
N4 N 0.1891(7) 0.1943(5) 0.9107(3) 0.0175(13) Uani 1 1 d . . . . .
N3 N 0.2144(7) 0.4768(5) 0.6784(3) 0.0151(12) Uani 1 1 d . . . . .
C1 C 0.8263(9) 0.7500(7) 0.6491(4) 0.0215(16) Uani 1 1 d . . . . .
H1 H 0.8668 0.8206 0.6894 0.026 Uiso 1 1 calc R U . . .
C5 C 0.6147(9) 0.5866(7) 0.5984(4) 0.0181(14) Uani 1 1 d . . . . .
C2 C 0.9314(8) 0.7168(9) 0.5838(4) 0.0258(15) Uani 1 1 d . . . . .
H2 H 1.0428 0.7633 0.5803 0.031 Uiso 1 1 calc R U . . .
C16 C 0.6287(10) 0.8613(7) 0.8320(5) 0.0259(16) Uani 1 1 d . . . . .
C15 C 0.3346(9) 0.7326(9) 0.8581(4) 0.0241(14) Uani 1 1 d . . . . .
C11 C 0.1368(9) 0.2689(7) 0.8243(4) 0.0204(15) Uani 1 1 d . . . . .
H11A H 0.2126 0.2339 0.7807 0.024 Uiso 1 1 calc R U . . .
H11B H 0.0081 0.2480 0.8025 0.024 Uiso 1 1 calc R U . . .
C8 C 0.1990(9) 0.3933(7) 0.6086(5) 0.0242(16) Uani 1 1 d . . . . .
H8 H 0.1046 0.3286 0.5932 0.029 Uiso 1 1 calc R U . . .
C6 C 0.4439(9) 0.5185(7) 0.6108(4) 0.0204(14) Uani 1 1 d . . . . .
C10 C 0.1594(9) 0.4223(7) 0.8309(4) 0.0180(13) Uani 1 1 d . . . . .
H10A H 0.2898 0.4445 0.8473 0.022 Uiso 1 1 calc R U . . .
H10B H 0.0915 0.4574 0.8776 0.022 Uiso 1 1 calc R U . . .
C14 C 0.3804(8) 0.2232(10) 0.9494(4) 0.0341(16) Uani 1 1 d . . . . .
H14A H 0.3937 0.3209 0.9627 0.051 Uiso 1 1 calc R U . . .
H14B H 0.4635 0.1975 0.9075 0.051 Uiso 1 1 calc R U . . .
H14C H 0.4096 0.1703 1.0035 0.051 Uiso 1 1 calc R U . . .
C4 C 0.7133(9) 0.5504(7) 0.5317(4) 0.0235(16) Uani 1 1 d . . . . .
H4 H 0.6707 0.4805 0.4914 0.028 Uiso 1 1 calc R U . . .
C13 C 0.0629(9) 0.2350(9) 0.9754(4) 0.0327(17) Uani 1 1 d . . . . .
H13A H 0.0751 0.1701 1.0244 0.049 Uiso 1 1 calc R U . . .
H13B H -0.0630 0.2343 0.9465 0.049 Uiso 1 1 calc R U . . .
H13C H 0.0943 0.3269 0.9976 0.049 Uiso 1 1 calc R U . . .
C3 C 0.8745(10) 0.6173(7) 0.5245(5) 0.0247(16) Uani 1 1 d . . . . .
H3 H 0.9446 0.5944 0.4790 0.030 Uiso 1 1 calc R U . . .
C9 C 0.0899(8) 0.4919(8) 0.7443(4) 0.0197(14) Uani 1 1 d . . . . .
H9A H -0.0297 0.4525 0.7211 0.024 Uiso 1 1 calc R U . . .
H9B H 0.0718 0.5904 0.7551 0.024 Uiso 1 1 calc R U . . .
C7 C 0.3425(9) 0.4175(7) 0.5636(5) 0.0266(16) Uani 1 1 d . . . . .
H7 H 0.3678 0.3746 0.5111 0.032 Uiso 1 1 calc R U . . .
C18 C 1.2943(10) 0.7011(9) 0.3579(6) 0.040(2) Uani 1 1 d . . . . .
N5 N 1.2019(9) 0.7132(10) 0.4086(6) 0.065(2) Uani 1 1 d . . . . .
C12 C 0.1719(13) 0.0430(7) 0.8956(6) 0.039(2) Uani 1 1 d . . . . .
H12A H 0.2503 0.0152 0.8521 0.059 Uiso 1 1 calc R U . . .
H12B H 0.0451 0.0204 0.8742 0.059 Uiso 1 1 calc R U . . .
H12C H 0.2092 -0.0053 0.9509 0.059 Uiso 1 1 calc R U . . .
C19 C 1.4170(12) 0.6862(9) 0.2912(6) 0.050(3) Uani 1 1 d . . . . .
H19A H 1.4242 0.7731 0.2601 0.075 Uiso 1 1 calc R U . . .
H19B H 1.3705 0.6150 0.2494 0.075 Uiso 1 1 calc R U . . .
H19C H 1.5385 0.6606 0.3194 0.075 Uiso 1 1 calc R U . . .
O3 O 0.2627(8) 0.9432(7) 0.6804(3) 0.0391(16) Uani 1 1 d . U . . .
C17 C 0.3359(10) 0.8724(7) 0.7017(6) 0.0197(16) Uani 1 1 d . 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
Mo1 C16 1.894(7) . ?
Mo1 C15 1.935(6) . ?
Mo1 C17 2.072(9) . ?
Mo1 N2 2.259(6) . ?
Mo1 N1 2.293(5) . ?
Mo1 Br1 2.7476(10) . ?
O1 C15 1.161(7) . ?
N1 C1 1.348(8) . ?
N1 C5 1.352(8) . ?
N2 N3 1.321(7) . ?
N2 C6 1.353(8) . ?
O2 C16 1.226(9) . ?
N4 C14 1.492(8) . ?
N4 C12 1.502(8) . ?
N4 C13 1.504(7) . ?
N4 C11 1.522(8) . ?
N3 C8 1.343(8) . ?
N3 C9 1.462(8) . ?
C1 C2 1.386(8) . ?
C1 H1 0.9500 . ?
C5 C4 1.379(9) . ?
C5 C6 1.463(9) . ?
C2 C3 1.364(11) . ?
C2 H2 0.9500 . ?
C11 C10 1.512(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C8 C7 1.361(9) . ?
C8 H8 0.9500 . ?
C6 C7 1.388(10) . ?
C10 C9 1.526(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C4 C3 1.378(10) . ?
C4 H4 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C3 H3 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C7 H7 0.9500 . ?
C18 N5 1.107(10) . ?
C18 C19 1.463(12) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O3 C17 0.914(8) . ?

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
C16 Mo1 C15 85.2(3) . . ?
C16 Mo1 C17 88.0(3) . . ?
C15 Mo1 C17 87.3(3) . . ?
C16 Mo1 N2 172.9(3) . . ?
C15 Mo1 N2 101.9(3) . . ?
C17 Mo1 N2 92.4(2) . . ?
C16 Mo1 N1 100.8(3) . . ?
C15 Mo1 N1 173.8(3) . . ?
C17 Mo1 N1 94.6(2) . . ?
N2 Mo1 N1 72.13(19) . . ?
C16 Mo1 Br1 97.3(2) . . ?
C15 Mo1 Br1 93.0(2) . . ?
C17 Mo1 Br1 174.63(19) . . ?
N2 Mo1 Br1 82.24(14) . . ?
N1 Mo1 Br1 84.49(13) . . ?
C1 N1 C5 117.2(5) . . ?
C1 N1 Mo1 125.2(4) . . ?
C5 N1 Mo1 117.5(4) . . ?
N3 N2 C6 106.5(6) . . ?
N3 N2 Mo1 136.6(4) . . ?
C6 N2 Mo1 116.9(4) . . ?
C14 N4 C12 107.8(6) . . ?
C14 N4 C13 108.9(5) . . ?
C12 N4 C13 108.4(6) . . ?
C14 N4 C11 112.3(5) . . ?
C12 N4 C11 109.4(5) . . ?
C13 N4 C11 110.0(5) . . ?
N2 N3 C8 110.9(5) . . ?
N2 N3 C9 120.8(5) . . ?
C8 N3 C9 128.3(6) . . ?
N1 C1 C2 122.2(7) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
N1 C5 C4 122.9(6) . . ?
N1 C5 C6 115.1(5) . . ?
C4 C5 C6 122.0(6) . . ?
C3 C2 C1 119.9(6) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
O2 C16 Mo1 177.3(7) . . ?
O1 C15 Mo1 179.4(7) . . ?
C10 C11 N4 113.8(5) . . ?
C10 C11 H11A 108.8 . . ?
N4 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
N4 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
N3 C8 C7 108.0(6) . . ?
N3 C8 H8 126.0 . . ?
C7 C8 H8 126.0 . . ?
N2 C6 C7 109.3(6) . . ?
N2 C6 C5 118.3(6) . . ?
C7 C6 C5 132.4(6) . . ?
C11 C10 C9 111.2(6) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C4 C5 119.0(7) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C3 C4 118.8(6) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
N3 C9 C10 112.8(5) . . ?
N3 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
N3 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C8 C7 C6 105.3(6) . . ?
C8 C7 H7 127.4 . . ?
C6 C7 H7 127.4 . . ?
N5 C18 C19 179.5(11) . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C17 Mo1 171.6(8) . . ?

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 N2 N3 C8 -1.6(7) . . . . ?
Mo1 N2 N3 C8 179.7(5) . . . . ?
C6 N2 N3 C9 -178.8(6) . . . . ?
Mo1 N2 N3 C9 2.4(9) . . . . ?
C5 N1 C1 C2 -0.5(9) . . . . ?
Mo1 N1 C1 C2 175.5(5) . . . . ?
C1 N1 C5 C4 -0.1(9) . . . . ?
Mo1 N1 C5 C4 -176.4(5) . . . . ?
C1 N1 C5 C6 179.3(6) . . . . ?
Mo1 N1 C5 C6 2.9(7) . . . . ?
N1 C1 C2 C3 0.9(10) . . . . ?
C14 N4 C11 C10 -57.1(7) . . . . ?
C12 N4 C11 C10 -176.7(6) . . . . ?
C13 N4 C11 C10 64.4(7) . . . . ?
N2 N3 C8 C7 0.6(8) . . . . ?
C9 N3 C8 C7 177.6(6) . . . . ?
N3 N2 C6 C7 1.9(8) . . . . ?
Mo1 N2 C6 C7 -179.1(5) . . . . ?
N3 N2 C6 C5 -178.0(5) . . . . ?
Mo1 N2 C6 C5 1.0(8) . . . . ?
N1 C5 C6 N2 -2.6(9) . . . . ?
C4 C5 C6 N2 176.7(6) . . . . ?
N1 C5 C6 C7 177.5(7) . . . . ?
C4 C5 C6 C7 -3.2(12) . . . . ?
N4 C11 C10 C9 -175.2(5) . . . . ?
N1 C5 C4 C3 0.2(10) . . . . ?
C6 C5 C4 C3 -179.0(6) . . . . ?
C1 C2 C3 C4 -0.7(10) . . . . ?
C5 C4 C3 C2 0.2(10) . . . . ?
N2 N3 C9 C10 -79.7(8) . . . . ?
C8 N3 C9 C10 103.6(8) . . . . ?
C11 C10 C9 N3 -75.6(7) . . . . ?
N3 C8 C7 C6 0.6(8) . . . . ?
N2 C6 C7 C8 -1.5(8) . . . . ?
C5 C6 C7 C8 178.4(7) . . . . ?

_refine_diff_density_max         1.313
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.116

####################################################################### 
# 
# 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_ig0215-L1
_database_code_depnum_ccdc_archive 'CCDC 1523642'
_audit_update_record             
;
2016-12-20 deposited with the CCDC.
2018-04-24 downloaded from the CCDC.
;

# ========================================================================= #

_audit_creation_method           'SHELXL-2014/7 and enCIFer'
_shelx_SHELXL_version_number     2014/7
_audit_creation_date             '18 December 2016'

# ========================================================================= #

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 N4, Br'
_chemical_formula_sum            'C14 H21 Br N4'
_chemical_formula_weight         325.26

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'
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                   9.0727(4)
_cell_length_b                   7.6409(3)
_cell_length_c                   22.0574(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.711(2)
_cell_angle_gamma                90
_cell_volume                     1523.93(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9865
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      30.95

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.691
_shelx_estimated_absorpt_T_min   0.629
_shelx_estimated_absorpt_T_max   0.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_process_details   
; 
'SADABS V2012/1 (Bruker AXS Inc.)' 
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            55072
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.659
_diffrn_reflns_theta_max         30.033
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997


_reflns_number_total             4440
_reflns_number_gt                3358
_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       'APEX2 (Bruker AXS Inc., 2012)'
_computing_cell_refinement       'SAINT (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2014)'


_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)+(0.0258P)²+0.4929P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4440
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0232
_refine_ls_wR_factor_ref         0.0564
_refine_ls_wR_factor_gt          0.0511
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.004
_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 0.22490(2) 0.74705(2) 0.51703(2) 0.02260(5) Uani 1 1 d . . . . .
N1 N 0.17038(14) 0.32298(16) 0.24850(5) 0.0260(3) Uani 1 1 d . . . . .
N2 N 0.31236(12) 0.63375(14) 0.28457(5) 0.0208(2) Uani 1 1 d . . . . .
N3 N 0.38286(13) 0.78944(15) 0.28531(5) 0.0231(2) Uani 1 1 d . . . . .
N4 N 0.30655(12) 1.24565(13) 0.44235(5) 0.0188(2) Uani 1 1 d . . . . .
C1 C 0.09546(17) 0.1796(2) 0.23032(7) 0.0309(3) Uani 1 1 d . . . . .
H1 H 0.0816 0.0920 0.2599 0.037 Uiso 1 1 calc R U . . .
C2 C 0.03653(17) 0.1496(2) 0.17143(7) 0.0327(3) Uani 1 1 d . . . . .
H2 H -0.0172 0.0456 0.1612 0.039 Uiso 1 1 calc R U . . .
C3 C 0.05764(17) 0.2743(2) 0.12795(7) 0.0309(3) Uani 1 1 d . . . . .
H3 H 0.0200 0.2573 0.0869 0.037 Uiso 1 1 calc R U . . .
C4 C 0.13514(15) 0.42556(19) 0.14531(6) 0.0253(3) Uani 1 1 d . . . . .
H4 H 0.1510 0.5140 0.1163 0.030 Uiso 1 1 calc R U . . .
C5 C 0.18932(14) 0.44567(17) 0.20595(6) 0.0202(3) Uani 1 1 d . . . . .
C6 C 0.26975(14) 0.60600(17) 0.22572(6) 0.0204(3) Uani 1 1 d . . . . .
C7 C 0.31286(18) 0.74533(18) 0.18924(6) 0.0276(3) Uani 1 1 d . . . . .
H7 H 0.2958 0.7574 0.1464 0.033 Uiso 1 1 calc R U . . .
C8 C 0.38511(18) 0.8599(2) 0.22946(7) 0.0312(3) Uani 1 1 d . . . . .
H8 H 0.4285 0.9684 0.2197 0.037 Uiso 1 1 calc R U . . .
C9 C 0.43291(16) 0.86840(18) 0.34339(6) 0.0241(3) Uani 1 1 d . . . . .
H9A H 0.5349 0.9129 0.3415 0.029 Uiso 1 1 calc R U . . .
H9B H 0.4348 0.7782 0.3757 0.029 Uiso 1 1 calc R U . . .
C10 C 0.33265(15) 1.01804(17) 0.35947(6) 0.0231(3) Uani 1 1 d . . . . .
H10A H 0.3376 1.1142 0.3296 0.028 Uiso 1 1 calc R U . . .
H10B H 0.2290 0.9770 0.3585 0.028 Uiso 1 1 calc R U . . .
C11 C 0.38383(15) 1.08268(16) 0.42267(6) 0.0195(3) Uani 1 1 d . . . . .
H11A H 0.3685 0.9882 0.4522 0.023 Uiso 1 1 calc R U . . .
H11B H 0.4914 1.1064 0.4242 0.023 Uiso 1 1 calc R U . . .
C12 C 0.14166(16) 1.2240(2) 0.43751(8) 0.0313(3) Uani 1 1 d . . . . .
H12A H 0.0963 1.3261 0.4554 0.047 Uiso 1 1 calc R U . . .
H12B H 0.1158 1.1182 0.4594 0.047 Uiso 1 1 calc R U . . .
H12C H 0.1052 1.2136 0.3946 0.047 Uiso 1 1 calc R U . . .
C13 C 0.34703(18) 1.40022(17) 0.40552(7) 0.0280(3) Uani 1 1 d . . . . .
H13A H 0.3026 1.5061 0.4212 0.042 Uiso 1 1 calc R U . . .
H13B H 0.3102 1.3827 0.3629 0.042 Uiso 1 1 calc R U . . .
H13C H 0.4549 1.4130 0.4083 0.042 Uiso 1 1 calc R U . . .
C14 C 0.35736(17) 1.27667(18) 0.50790(6) 0.0263(3) Uani 1 1 d . . . . .
H14A H 0.4654 1.2869 0.5123 0.039 Uiso 1 1 calc R U . . .
H14B H 0.3268 1.1783 0.5325 0.039 Uiso 1 1 calc R U . . .
H14C H 0.3131 1.3850 0.5218 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
N1 C1 1.3335(19) . ?
N1 C5 1.3476(17) . ?
N2 C6 1.3405(16) . ?
N2 N3 1.3501(15) . ?
N3 C8 1.3461(18) . ?
N3 C9 1.4545(17) . ?
N4 C13 1.4963(17) . ?
N4 C14 1.4999(17) . ?
N4 C12 1.5002(18) . ?
N4 C11 1.5102(16) . ?
C1 C2 1.383(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.376(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3950(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.4735(18) . ?
C6 C7 1.4091(18) . ?
C7 C8 1.374(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.5211(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5154(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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 N1 C5 116.94(12) . . ?
C6 N2 N3 104.46(10) . . ?
C8 N3 N2 112.59(11) . . ?
C8 N3 C9 127.80(12) . . ?
N2 N3 C9 119.31(11) . . ?
C13 N4 C14 109.21(11) . . ?
C13 N4 C12 109.64(11) . . ?
C14 N4 C12 108.17(11) . . ?
C13 N4 C11 110.75(10) . . ?
C14 N4 C11 107.11(10) . . ?
C12 N4 C11 111.87(10) . . ?
N1 C1 C2 124.52(14) . . ?
N1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C3 C2 C1 118.36(14) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 118.67(14) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C5 119.08(13) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 122.42(12) . . ?
N1 C5 C6 117.42(12) . . ?
C4 C5 C6 120.15(12) . . ?
N2 C6 C7 111.22(12) . . ?
N2 C6 C5 120.97(12) . . ?
C7 C6 C5 127.82(12) . . ?
C8 C7 C6 104.65(12) . . ?
C8 C7 H7 127.7 . . ?
C6 C7 H7 127.7 . . ?
N3 C8 C7 107.08(12) . . ?
N3 C8 H8 126.5 . . ?
C7 C8 H8 126.5 . . ?
N3 C9 C10 111.58(11) . . ?
N3 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N3 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 108.40(11) . . ?
C11 C10 H10A 110.0 . . ?
C9 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
C9 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
N4 C11 C10 114.76(10) . . ?
N4 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
N4 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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 N2 N3 C8 0.34(16) . . . . ?
C6 N2 N3 C9 174.52(12) . . . . ?
C5 N1 C1 C2 -0.2(2) . . . . ?
N1 C1 C2 C3 1.0(3) . . . . ?
C1 C2 C3 C4 -1.0(2) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C1 N1 C5 C4 -0.6(2) . . . . ?
C1 N1 C5 C6 178.99(13) . . . . ?
C3 C4 C5 N1 0.5(2) . . . . ?
C3 C4 C5 C6 -179.03(13) . . . . ?
N3 N2 C6 C7 -0.34(15) . . . . ?
N3 N2 C6 C5 179.32(11) . . . . ?
N1 C5 C6 N2 -4.89(19) . . . . ?
C4 C5 C6 N2 174.68(13) . . . . ?
N1 C5 C6 C7 174.70(14) . . . . ?
C4 C5 C6 C7 -5.7(2) . . . . ?
N2 C6 C7 C8 0.22(17) . . . . ?
C5 C6 C7 C8 -179.40(14) . . . . ?
N2 N3 C8 C7 -0.21(18) . . . . ?
C9 N3 C8 C7 -173.79(14) . . . . ?
C6 C7 C8 N3 -0.01(17) . . . . ?
C8 N3 C9 C10 69.41(19) . . . . ?
N2 N3 C9 C10 -103.80(14) . . . . ?
N3 C9 C10 C11 175.11(11) . . . . ?
C13 N4 C11 C10 -67.84(14) . . . . ?
C14 N4 C11 C10 173.16(11) . . . . ?
C12 N4 C11 C10 54.80(15) . . . . ?
C9 C10 C11 N4 173.06(11) . . . . ?

_refine_diff_density_max         0.363
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.055

