# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_HG_SS16
_database_code_depnum_ccdc_archive 'CCDC 1061952'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 Br N O'
_chemical_formula_weight         200.04
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_space_group_IT_number           14
_symmetry_space_group_name_H-M   P2(1)/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                   16.189(2)
_cell_length_b                   4.6448(7)
_cell_length_c                   9.8821(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.866(5)
_cell_angle_gamma                90
_cell_volume                     742.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1957
_cell_measurement_theta_min      4.13
_cell_measurement_theta_max      30.51

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    5.463
_shelx_estimated_absorpt_T_min   0.342
_shelx_estimated_absorpt_T_max   0.811
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.624
_exptl_absorpt_correction_T_max  0.811
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating anode X-ray tube'
_diffrn_source_type              'Bruker-Nonius FR 591'
_diffrn_source_power             50
_diffrn_source_current           70
_diffrn_source_size              '0.3 mm x 0.3 mm fine focus'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            3504
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.259
_diffrn_reflns_theta_max         30.536
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             1998
_reflns_number_gt                1565
_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 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1998
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1579
_refine_ls_wR_factor_gt          0.1469
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
Br1 Br 0.42413(2) 0.70296(10) 0.66773(4) 0.02551(19) Uani 1 1 d . . . . .
N1 N 0.0597(2) 0.7826(7) 0.3821(3) 0.0217(7) Uani 1 1 d . . . . .
H1A H 0.0133 0.8718 0.3839 0.026 Uiso 1 1 calc R U . . .
H1B H 0.0745 0.7048 0.3081 0.026 Uiso 1 1 calc R U . . .
O1 O 0.09059(16) 0.8731(7) 0.6037(2) 0.0217(6) Uani 1 1 d . . . . .
C1 C 0.1901(2) 0.6129(8) 0.4817(3) 0.0162(7) Uani 1 1 d . . . . .
C2 C 0.2014(2) 0.3977(9) 0.3863(3) 0.0196(7) Uani 1 1 d . . . . .
H2 H 0.1574 0.3387 0.3289 0.024 Uiso 1 1 calc R U . . .
C3 C 0.2792(3) 0.2709(9) 0.3771(4) 0.0234(8) Uani 1 1 d . . . . .
H3 H 0.2863 0.1255 0.3140 0.028 Uiso 1 1 calc R U . . .
C4 C 0.3455(3) 0.3579(9) 0.4601(4) 0.0221(8) Uani 1 1 d . . . . .
H4 H 0.3973 0.2740 0.4531 0.027 Uiso 1 1 calc R U . . .
C5 C 0.3333(2) 0.5736(9) 0.5547(3) 0.0198(7) Uani 1 1 d . . . . .
C6 C 0.2558(2) 0.7011(8) 0.5682(4) 0.0169(7) Uani 1 1 d . . . . .
H6 H 0.2484 0.8415 0.6335 0.020 Uiso 1 1 calc R U . . .
C7 C 0.1087(2) 0.7648(8) 0.4937(4) 0.0173(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
Br1 C5 1.899(4) . ?
N1 C7 1.329(5) . ?
O1 C7 1.246(4) . ?
C1 C2 1.392(5) . ?
C1 C6 1.392(5) . ?
C1 C7 1.504(5) . ?
C2 C3 1.397(6) . ?
C3 C4 1.379(6) . ?
C4 C5 1.391(5) . ?
C5 C6 1.400(5) . ?

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
C2 C1 C6 120.3(3) . . ?
C2 C1 C7 122.4(3) . . ?
C6 C1 C7 117.3(3) . . ?
C1 C2 C3 119.8(4) . . ?
C4 C3 C2 121.0(4) . . ?
C3 C4 C5 118.6(4) . . ?
C4 C5 C6 121.8(4) . . ?
C4 C5 Br1 119.4(3) . . ?
C6 C5 Br1 118.8(3) . . ?
C1 C6 C5 118.5(3) . . ?
O1 C7 N1 122.8(4) . . ?
O1 C7 C1 120.3(3) . . ?
N1 C7 C1 116.9(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 C1 C2 C3 -0.3(5) . . . . ?
C7 C1 C2 C3 178.0(3) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C3 C4 C5 Br1 -178.7(3) . . . . ?
C2 C1 C6 C5 1.5(5) . . . . ?
C7 C1 C6 C5 -176.8(3) . . . . ?
C4 C5 C6 C1 -1.7(5) . . . . ?
Br1 C5 C6 C1 177.7(3) . . . . ?
C2 C1 C7 O1 153.9(3) . . . . ?
C6 C1 C7 O1 -27.8(5) . . . . ?
C2 C1 C7 N1 -27.8(5) . . . . ?
C6 C1 C7 N1 150.5(3) . . . . ?

_refine_diff_density_max         1.139
_refine_diff_density_min         -1.341
_refine_diff_density_rms         0.209
_shelxl_version_number           2014-3
####################################################################### 
# 
# 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_HG_SS20_0m
_database_code_depnum_ccdc_archive 'CCDC 1061953'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 Br N O'
_chemical_formula_weight         200.04
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'

_symmetry_cell_setting           Monoclinic
_space_group_IT_number           14
_symmetry_space_group_name_H-M   P2(1)/n
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   5.0263(6)
_cell_length_b                   10.9683(15)
_cell_length_c                   13.3113(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.465(3)
_cell_angle_gamma                90
_cell_volume                     732.51(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    707
_cell_measurement_theta_min      4.02
_cell_measurement_theta_max      31.17

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    5.535
_shelx_estimated_absorpt_T_min   0.248
_shelx_estimated_absorpt_T_max   0.769
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_T_max  0.769
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating anode X-ray tube'
_diffrn_source_type              'Bruker-Nonius FR 591'
_diffrn_source_power             50
_diffrn_source_current           70
_diffrn_source_size              '0.3 mm x 0.3 mm fine focus'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            1110
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_av_R_equivalents  0.0073
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.408
_diffrn_reflns_theta_max         31.971
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.556
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.556
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.556
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             980
_reflns_number_gt                903
_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 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_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)+(0.0271P)²+0.5327P] 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         980
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0197
_refine_ls_wR_factor_ref         0.0512
_refine_ls_wR_factor_gt          0.0499
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 0.15422(4) -0.05399(3) 0.18586(2) 0.02113(13) Uani 1 1 d . . . . .
N1 N 0.7508(4) 0.0609(2) 0.41344(17) 0.0184(7) Uani 1 1 d . . . . .
H1A H 0.7461 0.0375 0.4750 0.022 Uiso 1 1 calc R U . . .
H1B H 0.9015 0.0718 0.3874 0.022 Uiso 1 1 calc R U . . .
O1 O 0.3034(3) 0.06576(19) 0.39322(14) 0.0187(6) Uani 1 1 d . . . . .
C1 C 0.5239(4) 0.0804(3) 0.3583(2) 0.0164(8) Uani 1 1 d . . . . .
C2 C 0.5521(4) 0.1235(3) 0.2531(2) 0.0140(8) Uani 1 1 d . . . . .
C3 C 0.3947(4) 0.0778(3) 0.1706(2) 0.0166(8) Uani 1 1 d . . . . .
C4 C 0.4205(5) 0.1227(3) 0.0743(2) 0.0212(9) Uani 1 1 d . . . . .
H4 H 0.3102 0.0940 0.0208 0.025 Uiso 1 1 calc R U . . .
C5 C 0.6103(5) 0.2100(4) 0.0582(2) 0.0257(10) Uani 1 1 d . . . . .
H5 H 0.6299 0.2392 -0.0065 0.031 Uiso 1 1 calc R U . . .
C6 C 0.7736(5) 0.2548(3) 0.1385(2) 0.0247(9) Uani 1 1 d . . . . .
H6 H 0.9012 0.3140 0.1277 0.030 Uiso 1 1 calc R U . . .
C7 C 0.7434(4) 0.2103(3) 0.2341(2) 0.0179(8) Uani 1 1 d . . . . .
H7 H 0.8543 0.2393 0.2873 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
Br1 C3 1.903(3) . ?
N1 C1 1.336(2) . ?
O1 C1 1.238(3) . ?
C1 C2 1.492(4) . ?
C2 C7 1.387(4) . ?
C2 C3 1.407(3) . ?
C3 C4 1.387(4) . ?
C4 C5 1.377(5) . ?
C5 C6 1.398(4) . ?
C6 C7 1.380(4) . ?

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
O1 C1 N1 121.8(3) . . ?
O1 C1 C2 122.10(18) . . ?
N1 C1 C2 116.1(2) . . ?
C7 C2 C3 117.7(3) . . ?
C7 C2 C1 119.6(2) . . ?
C3 C2 C1 122.6(2) . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 Br1 117.7(2) . . ?
C2 C3 Br1 121.2(2) . . ?
C5 C4 C3 119.7(2) . . ?
C4 C5 C6 120.4(3) . . ?
C7 C6 C5 119.2(3) . . ?
C6 C7 C2 121.8(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
O1 C1 C2 C7 137.3(3) . . . . ?
N1 C1 C2 C7 -41.4(4) . . . . ?
O1 C1 C2 C3 -44.0(4) . . . . ?
N1 C1 C2 C3 137.3(3) . . . . ?
C7 C2 C3 C4 -3.3(4) . . . . ?
C1 C2 C3 C4 177.9(3) . . . . ?
C7 C2 C3 Br1 173.0(2) . . . . ?
C1 C2 C3 Br1 -5.7(4) . . . . ?
C2 C3 C4 C5 2.7(4) . . . . ?
Br1 C3 C4 C5 -173.8(2) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C5 C6 C7 C2 -1.1(5) . . . . ?
C3 C2 C7 C6 2.6(4) . . . . ?
C1 C2 C7 C6 -178.7(3) . . . . ?

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.051
_shelxl_version_number           2014-3
####################################################################### 
# 
# 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_hg513frac3_0m
_database_code_depnum_ccdc_archive 'CCDC 1061954'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 N2 O2'
_chemical_formula_weight         340.37

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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                   9.3024(10)
_cell_length_b                   8.3301(11)
_cell_length_c                   21.227(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.100(5)
_cell_angle_gamma                90.00
_cell_volume                     1640.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2520
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      35.80

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_suppport 
'magnetic support whith 10 micron nylon fiber cryoloop'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_type              'Bruker-Nonius FR 591'
_diffrn_source_power             50
_diffrn_source_current           70
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18213
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_sigmaI/netI    0.1132
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         36.60
_reflns_number_total             7548
_reflns_number_gt                4222
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0957P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7548
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1347
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1887
_refine_ls_wR_factor_gt          0.1531
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.67649(16) 0.04625(16) -0.04580(7) 0.0136(3) Uani 1 1 d . . .
C2 C 0.81489(16) 0.05503(16) -0.07745(7) 0.0125(3) Uani 1 1 d . . .
C3 C 0.91056(16) -0.07505(16) -0.06723(7) 0.0148(3) Uani 1 1 d . . .
H3 H 0.8863 -0.1611 -0.0406 0.018 Uiso 1 1 calc R . .
C4 C 1.03729(16) -0.07803(16) -0.09521(7) 0.0147(3) Uani 1 1 d . . .
H4 H 1.1004 -0.1671 -0.0887 0.018 Uiso 1 1 calc R . .
C5 C 1.07576(16) 0.05067(16) -0.13390(7) 0.0125(3) Uani 1 1 d . . .
C6 C 1.20878(17) 0.05079(17) -0.16200(7) 0.0162(3) Uani 1 1 d . . .
H6 H 1.2719 -0.0384 -0.1559 0.019 Uiso 1 1 calc R . .
C7 C 1.24777(18) 0.17734(18) -0.19780(7) 0.0185(3) Uani 1 1 d . . .
H7 H 1.3377 0.1763 -0.2163 0.022 Uiso 1 1 calc R . .
C8 C 1.15488(18) 0.30907(18) -0.20721(7) 0.0191(3) Uani 1 1 d . . .
H8 H 1.1825 0.3970 -0.2322 0.023 Uiso 1 1 calc R . .
C9 C 1.02530(17) 0.31252(16) -0.18095(7) 0.0155(3) Uani 1 1 d . . .
H9 H 0.9637 0.4027 -0.1879 0.019 Uiso 1 1 calc R . .
C10 C 0.98154(15) 0.18374(15) -0.14352(7) 0.0122(2) Uani 1 1 d . . .
C11 C 0.84763(15) 0.18343(15) -0.11472(7) 0.0114(2) Uani 1 1 d . . .
C12 C 0.74740(16) 0.32272(15) -0.12196(7) 0.0122(3) Uani 1 1 d . . .
C13 C 0.73413(16) 0.42897(15) -0.06990(7) 0.0133(3) Uani 1 1 d . . .
C14 C 0.81950(18) 0.41283(18) -0.01270(7) 0.0174(3) Uani 1 1 d . . .
H14 H 0.8917 0.3320 -0.0088 0.021 Uiso 1 1 calc R . .
C15 C 0.79989(19) 0.51165(19) 0.03720(8) 0.0211(3) Uani 1 1 d . . .
H15 H 0.8587 0.4995 0.0754 0.025 Uiso 1 1 calc R . .
C16 C 0.69316(19) 0.63145(18) 0.03248(8) 0.0211(3) Uani 1 1 d . . .
H16 H 0.6789 0.6983 0.0678 0.025 Uiso 1 1 calc R . .
C17 C 0.61033(18) 0.65207(16) -0.02222(8) 0.0184(3) Uani 1 1 d . . .
H17 H 0.5387 0.7336 -0.0250 0.022 Uiso 1 1 calc R . .
C18 C 0.62976(17) 0.55327(15) -0.07516(7) 0.0147(3) Uani 1 1 d . . .
C19 C 0.54726(17) 0.57535(17) -0.13287(8) 0.0174(3) Uani 1 1 d . . .
H19 H 0.4782 0.6594 -0.1367 0.021 Uiso 1 1 calc R . .
C20 C 0.56552(17) 0.47736(16) -0.18325(7) 0.0159(3) Uani 1 1 d . . .
H20 H 0.5118 0.4956 -0.2223 0.019 Uiso 1 1 calc R . .
C21 C 0.66465(16) 0.34873(15) -0.17704(7) 0.0127(3) Uani 1 1 d . . .
C22 C 0.66844(16) 0.23197(17) -0.23022(7) 0.0142(3) Uani 1 1 d . . .
N1 N 0.55667(14) 0.04702(15) -0.08372(6) 0.0165(3) Uani 1 1 d . . .
H1A H 0.4723 0.0378 -0.0678 0.020 Uiso 1 1 calc R . .
H1B H 0.5616 0.0568 -0.1248 0.020 Uiso 1 1 calc R . .
N2 N 0.70635(16) 0.29074(15) -0.28458(6) 0.0198(3) Uani 1 1 d . . .
H2A H 0.7073 0.2281 -0.3179 0.024 Uiso 1 1 calc R . .
H2B H 0.7306 0.3925 -0.2874 0.024 Uiso 1 1 calc R . .
O1 O 0.67914(12) 0.03314(13) 0.01202(5) 0.0179(2) Uani 1 1 d . . .
O2 O 0.63307(13) 0.09044(13) -0.22280(5) 0.0182(2) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 O1 1.2307(18) . ?
C1 N1 1.328(2) . ?
C1 C2 1.4960(19) . ?
C2 C11 1.3773(18) . ?
C2 C3 1.409(2) . ?
C3 C4 1.358(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.4121(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.412(2) . ?
C5 C10 1.4188(19) . ?
C6 C7 1.364(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.402(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.364(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.4121(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.4263(19) . ?
C11 C12 1.4896(19) . ?
C12 C21 1.370(2) . ?
C12 C13 1.4280(19) . ?
C13 C14 1.409(2) . ?
C13 C18 1.418(2) . ?
C14 C15 1.364(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.406(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.358(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.415(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.410(2) . ?
C19 C20 1.365(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.414(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.4924(19) . ?
C22 O2 1.2371(17) . ?
C22 N2 1.3242(18) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?

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
O1 C1 N1 124.14(14) . . ?
O1 C1 C2 119.72(14) . . ?
N1 C1 C2 116.08(13) . . ?
C11 C2 C3 121.49(13) . . ?
C11 C2 C1 121.92(12) . . ?
C3 C2 C1 116.59(12) . . ?
C4 C3 C2 120.35(13) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.31(13) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.83(13) . . ?
C6 C5 C10 119.33(12) . . ?
C4 C5 C10 119.82(13) . . ?
C7 C6 C5 120.81(14) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.91(14) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 120.79(14) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.84(14) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C5 118.33(13) . . ?
C9 C10 C11 122.57(13) . . ?
C5 C10 C11 119.10(12) . . ?
C2 C11 C10 118.91(12) . . ?
C2 C11 C12 120.11(12) . . ?
C10 C11 C12 120.91(11) . . ?
C21 C12 C13 119.20(12) . . ?
C21 C12 C11 121.37(12) . . ?
C13 C12 C11 119.41(13) . . ?
C14 C13 C18 118.55(13) . . ?
C14 C13 C12 122.22(13) . . ?
C18 C13 C12 119.21(14) . . ?
C15 C14 C13 120.88(15) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 120.39(16) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 120.35(14) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.58(14) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 121.43(13) . . ?
C19 C18 C13 119.38(13) . . ?
C17 C18 C13 119.19(15) . . ?
C20 C19 C18 120.78(13) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 119.79(15) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C12 C21 C20 121.49(13) . . ?
C12 C21 C22 120.01(12) . . ?
C20 C21 C22 118.29(14) . . ?
O2 C22 N2 123.57(13) . . ?
O2 C22 C21 120.26(13) . . ?
N2 C22 C21 116.13(12) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C22 N2 H2A 120.0 . . ?
C22 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
O1 C1 C2 C11 -121.96(16) . . . . ?
N1 C1 C2 C11 60.62(19) . . . . ?
O1 C1 C2 C3 58.05(18) . . . . ?
N1 C1 C2 C3 -119.37(15) . . . . ?
C11 C2 C3 C4 -1.3(2) . . . . ?
C1 C2 C3 C4 178.72(14) . . . . ?
C2 C3 C4 C5 1.2(2) . . . . ?
C3 C4 C5 C6 178.44(15) . . . . ?
C3 C4 C5 C10 0.0(2) . . . . ?
C4 C5 C6 C7 -178.00(15) . . . . ?
C10 C5 C6 C7 0.4(2) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C6 C7 C8 C9 0.0(2) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C8 C9 C10 C5 0.0(2) . . . . ?
C8 C9 C10 C11 179.35(15) . . . . ?
C6 C5 C10 C9 -0.3(2) . . . . ?
C4 C5 C10 C9 178.14(14) . . . . ?
C6 C5 C10 C11 -179.64(14) . . . . ?
C4 C5 C10 C11 -1.2(2) . . . . ?
C3 C2 C11 C10 0.1(2) . . . . ?
C1 C2 C11 C10 -179.91(14) . . . . ?
C3 C2 C11 C12 -176.96(14) . . . . ?
C1 C2 C11 C12 3.0(2) . . . . ?
C9 C10 C11 C2 -178.19(14) . . . . ?
C5 C10 C11 C2 1.1(2) . . . . ?
C9 C10 C11 C12 -1.2(2) . . . . ?
C5 C10 C11 C12 178.16(13) . . . . ?
C2 C11 C12 C21 -107.16(16) . . . . ?
C10 C11 C12 C21 75.86(18) . . . . ?
C2 C11 C12 C13 71.07(18) . . . . ?
C10 C11 C12 C13 -105.91(16) . . . . ?
C21 C12 C13 C14 -177.66(13) . . . . ?
C11 C12 C13 C14 4.1(2) . . . . ?
C21 C12 C13 C18 3.6(2) . . . . ?
C11 C12 C13 C18 -174.66(12) . . . . ?
C18 C13 C14 C15 1.7(2) . . . . ?
C12 C13 C14 C15 -177.01(14) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C14 C15 C16 C17 -1.3(2) . . . . ?
C15 C16 C17 C18 0.2(2) . . . . ?
C16 C17 C18 C19 -178.42(14) . . . . ?
C16 C17 C18 C13 1.8(2) . . . . ?
C14 C13 C18 C19 177.50(13) . . . . ?
C12 C13 C18 C19 -3.7(2) . . . . ?
C14 C13 C18 C17 -2.8(2) . . . . ?
C12 C13 C18 C17 176.01(13) . . . . ?
C17 C18 C19 C20 -178.90(14) . . . . ?
C13 C18 C19 C20 0.8(2) . . . . ?
C18 C19 C20 C21 2.2(2) . . . . ?
C13 C12 C21 C20 -0.6(2) . . . . ?
C11 C12 C21 C20 177.61(13) . . . . ?
C13 C12 C21 C22 -175.23(12) . . . . ?
C11 C12 C21 C22 3.0(2) . . . . ?
C19 C20 C21 C12 -2.3(2) . . . . ?
C19 C20 C21 C22 172.39(13) . . . . ?
C12 C21 C22 O2 60.1(2) . . . . ?
C20 C21 C22 O2 -114.69(16) . . . . ?
C12 C21 C22 N2 -122.11(15) . . . . ?
C20 C21 C22 N2 63.11(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.933
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.086
####################################################################### 
# 
# 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_hg492f3-4
_database_code_depnum_ccdc_archive 'CCDC 1061955'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H12 N2'
_chemical_formula_weight         304.34

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   12.3869(6)
_cell_length_b                   7.7560(4)
_cell_length_c                   16.0899(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.514(3)
_cell_angle_gamma                90.00
_cell_volume                     1538.65(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5201
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      36.03

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9770
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
; 
 TWINABS Version 2008/4 Bruker AXS
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_suppport 
'magnetic support whith 10 micron nylon fiber cryoloop'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_type              'Bruker-Nonius FR 591'
_diffrn_source_power             50
_diffrn_source_current           70
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            7412
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0541
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         36.38
_reflns_number_total             7412
_reflns_number_gt                4819
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 v2009.1-0'
_computing_cell_refinement       'Bruker APEX2 v2009.1-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1086P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7412
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1710
_refine_ls_wR_factor_gt          0.1588
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.31009(6) 0.61949(11) 0.15085(6) 0.01715(16) Uani 1 1 d . . .
N1 N 0.23649(7) 1.02007(12) 0.22244(7) 0.0316(2) Uani 1 1 d . . .
C2 C 0.35874(7) 0.77338(12) 0.17679(6) 0.01947(17) Uani 1 1 d . . .
N2 N 0.27105(7) 0.44329(13) 0.35207(6) 0.0304(2) Uani 1 1 d . . .
C3 C 0.47186(7) 0.79971(13) 0.17725(6) 0.02183(18) Uani 1 1 d . . .
H3 H 0.5034 0.9066 0.1954 0.026 Uiso 1 1 calc R . .
C4 C 0.53517(7) 0.67012(12) 0.15139(6) 0.02153(18) Uani 1 1 d . . .
H4 H 0.6112 0.6872 0.1519 0.026 Uiso 1 1 calc R . .
C5 C 0.48934(6) 0.51084(12) 0.12388(6) 0.01866(17) Uani 1 1 d . . .
C6 C 0.55433(7) 0.37570(13) 0.09667(7) 0.02416(19) Uani 1 1 d . . .
H6 H 0.6305 0.3914 0.0977 0.029 Uiso 1 1 calc R . .
C7 C 0.50895(8) 0.22303(14) 0.06888(7) 0.0271(2) Uani 1 1 d . . .
H7 H 0.5535 0.1337 0.0506 0.033 Uiso 1 1 calc R . .
C8 C 0.39620(8) 0.19808(13) 0.06739(7) 0.0264(2) Uani 1 1 d . . .
H8 H 0.3650 0.0924 0.0472 0.032 Uiso 1 1 calc R . .
C9 C 0.33119(7) 0.32430(12) 0.09468(6) 0.02153(18) Uani 1 1 d . . .
H9 H 0.2555 0.3046 0.0944 0.026 Uiso 1 1 calc R . .
C10 C 0.37566(6) 0.48427(11) 0.12338(6) 0.01763(16) Uani 1 1 d . . .
C11 C 0.19030(6) 0.60133(11) 0.15186(6) 0.01707(16) Uani 1 1 d . . .
C12 C 0.14720(7) 0.53404(12) 0.22113(6) 0.01877(17) Uani 1 1 d . . .
C13 C 0.03352(7) 0.52750(12) 0.22665(6) 0.02058(18) Uani 1 1 d . . .
H13 H 0.0056 0.4784 0.2743 0.025 Uiso 1 1 calc R . .
C14 C -0.03506(7) 0.59237(12) 0.16306(6) 0.02078(18) Uani 1 1 d . . .
H14 H -0.1110 0.5907 0.1672 0.025 Uiso 1 1 calc R . .
C15 C 0.00529(6) 0.66223(11) 0.09089(6) 0.01793(16) Uani 1 1 d . . .
C16 C -0.06579(7) 0.73069(13) 0.02480(6) 0.02219(18) Uani 1 1 d . . .
H16 H -0.1416 0.7326 0.0295 0.027 Uiso 1 1 calc R . .
C17 C -0.02661(8) 0.79389(13) -0.04543(7) 0.0255(2) Uani 1 1 d . . .
H17 H -0.0751 0.8393 -0.0894 0.031 Uiso 1 1 calc R . .
C18 C 0.08557(8) 0.79196(14) -0.05289(7) 0.0262(2) Uani 1 1 d . . .
H18 H 0.1121 0.8338 -0.1026 0.031 Uiso 1 1 calc R . .
C19 C 0.15704(7) 0.73072(13) 0.01025(6) 0.02230(18) Uani 1 1 d . . .
H19 H 0.2327 0.7328 0.0047 0.027 Uiso 1 1 calc R . .
C20 C 0.11879(6) 0.66411(11) 0.08402(6) 0.01717(16) Uani 1 1 d . . .
C21 C 0.29139(7) 0.91091(13) 0.20280(7) 0.02343(19) Uani 1 1 d . . .
C22 C 0.21801(7) 0.48001(12) 0.29242(6) 0.02227(19) 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
C1 C2 1.3834(12) . ?
C1 C10 1.4226(12) . ?
C1 C11 1.4922(11) . ?
N1 C21 1.1491(13) . ?
C2 C3 1.4153(12) . ?
C2 C21 1.4408(13) . ?
N2 C22 1.1458(14) . ?
C3 C4 1.3642(13) . ?
C4 C5 1.4129(13) . ?
C5 C6 1.4164(13) . ?
C5 C10 1.4224(11) . ?
C6 C7 1.3674(15) . ?
C7 C8 1.4079(14) . ?
C8 C9 1.3666(13) . ?
C9 C10 1.4167(13) . ?
C11 C12 1.3834(12) . ?
C11 C20 1.4239(12) . ?
C12 C13 1.4204(11) . ?
C12 C22 1.4378(13) . ?
C13 C14 1.3618(14) . ?
C14 C15 1.4154(13) . ?
C15 C16 1.4170(13) . ?
C15 C20 1.4209(11) . ?
C16 C17 1.3631(14) . ?
C17 C18 1.4062(13) . ?
C18 C19 1.3671(14) . ?
C19 C20 1.4171(13) . ?

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
C2 C1 C10 118.99(7) . . ?
C2 C1 C11 118.88(7) . . ?
C10 C1 C11 122.13(8) . . ?
C1 C2 C3 121.90(8) . . ?
C1 C2 C21 118.61(8) . . ?
C3 C2 C21 119.49(8) . . ?
C4 C3 C2 119.34(8) . . ?
C3 C4 C5 120.95(8) . . ?
C4 C5 C6 121.38(8) . . ?
C4 C5 C10 119.75(8) . . ?
C6 C5 C10 118.87(8) . . ?
C7 C6 C5 120.93(8) . . ?
C6 C7 C8 120.03(9) . . ?
C9 C8 C7 120.68(9) . . ?
C8 C9 C10 120.63(8) . . ?
C9 C10 C5 118.84(8) . . ?
C9 C10 C1 122.09(7) . . ?
C5 C10 C1 119.07(8) . . ?
C12 C11 C20 119.13(7) . . ?
C12 C11 C1 120.37(8) . . ?
C20 C11 C1 120.36(8) . . ?
C11 C12 C13 121.70(8) . . ?
C11 C12 C22 119.97(8) . . ?
C13 C12 C22 118.17(8) . . ?
C14 C13 C12 119.37(8) . . ?
C13 C14 C15 120.92(8) . . ?
C14 C15 C16 121.08(8) . . ?
C14 C15 C20 119.86(8) . . ?
C16 C15 C20 119.06(8) . . ?
C17 C16 C15 120.79(8) . . ?
C16 C17 C18 120.02(9) . . ?
C19 C18 C17 120.99(9) . . ?
C18 C19 C20 120.29(8) . . ?
C19 C20 C15 118.81(8) . . ?
C19 C20 C11 122.23(7) . . ?
C15 C20 C11 118.95(8) . . ?
N1 C21 C2 178.89(12) . . ?
N2 C22 C12 175.93(10) . . ?

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
C10 C1 C2 C3 -0.39(14) . . . . ?
C11 C1 C2 C3 -179.84(9) . . . . ?
C10 C1 C2 C21 178.67(9) . . . . ?
C11 C1 C2 C21 -0.77(14) . . . . ?
C1 C2 C3 C4 0.04(15) . . . . ?
C21 C2 C3 C4 -179.01(10) . . . . ?
C2 C3 C4 C5 0.30(15) . . . . ?
C3 C4 C5 C6 179.80(10) . . . . ?
C3 C4 C5 C10 -0.29(15) . . . . ?
C4 C5 C6 C7 -178.93(10) . . . . ?
C10 C5 C6 C7 1.16(15) . . . . ?
C5 C6 C7 C8 -0.30(16) . . . . ?
C6 C7 C8 C9 -0.97(17) . . . . ?
C7 C8 C9 C10 1.34(17) . . . . ?
C8 C9 C10 C5 -0.46(15) . . . . ?
C8 C9 C10 C1 178.90(10) . . . . ?
C4 C5 C10 C9 179.31(9) . . . . ?
C6 C5 C10 C9 -0.78(13) . . . . ?
C4 C5 C10 C1 -0.07(13) . . . . ?
C6 C5 C10 C1 179.85(9) . . . . ?
C2 C1 C10 C9 -178.96(9) . . . . ?
C11 C1 C10 C9 0.47(14) . . . . ?
C2 C1 C10 C5 0.40(13) . . . . ?
C11 C1 C10 C5 179.82(8) . . . . ?
C2 C1 C11 C12 -92.19(11) . . . . ?
C10 C1 C11 C12 88.38(11) . . . . ?
C2 C1 C11 C20 83.39(11) . . . . ?
C10 C1 C11 C20 -96.03(11) . . . . ?
C20 C11 C12 C13 -0.62(13) . . . . ?
C1 C11 C12 C13 175.02(8) . . . . ?
C20 C11 C12 C22 -176.09(8) . . . . ?
C1 C11 C12 C22 -0.45(13) . . . . ?
C11 C12 C13 C14 -1.44(14) . . . . ?
C22 C12 C13 C14 174.11(9) . . . . ?
C12 C13 C14 C15 1.52(14) . . . . ?
C13 C14 C15 C16 -179.65(9) . . . . ?
C13 C14 C15 C20 0.42(14) . . . . ?
C14 C15 C16 C17 -178.36(9) . . . . ?
C20 C15 C16 C17 1.56(14) . . . . ?
C15 C16 C17 C18 -0.11(16) . . . . ?
C16 C17 C18 C19 -1.42(16) . . . . ?
C17 C18 C19 C20 1.44(16) . . . . ?
C18 C19 C20 C15 0.04(14) . . . . ?
C18 C19 C20 C11 -179.06(9) . . . . ?
C14 C15 C20 C19 178.41(9) . . . . ?
C16 C15 C20 C19 -1.52(13) . . . . ?
C14 C15 C20 C11 -2.46(13) . . . . ?
C16 C15 C20 C11 177.61(8) . . . . ?
C12 C11 C20 C19 -178.37(9) . . . . ?
C1 C11 C20 C19 5.99(13) . . . . ?
C12 C11 C20 C15 2.53(13) . . . . ?
C1 C11 C20 C15 -173.11(8) . . . . ?
C1 C2 C21 N1 -44(6) . . . . ?
C3 C2 C21 N1 135(6) . . . . ?
C11 C12 C22 N2 125.4(15) . . . . ?
C13 C12 C22 N2 -50.2(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        36.38
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.087
####################################################################### 
# 
# 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_hg513_0m
_database_code_depnum_ccdc_archive 'CCDC 1061956'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H12 N2'
_chemical_formula_weight         304.34

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   7.8740(8)
_cell_length_b                   7.9775(8)
_cell_length_c                   12.3173(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.715(2)
_cell_angle_gamma                90.00
_cell_volume                     772.84(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3393
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      38.44

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9697
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_suppport 
'magnetic support whith 10 micron nylon fiber cryoloop'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_type              'Bruker-Nonius FR 591'
_diffrn_source_power             50
_diffrn_source_current           70
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3539
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         28.99
_reflns_number_total             2638
_reflns_number_gt                2561
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0708P)²+0.1031P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_number_reflns         2638
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1111
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.055
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1008(2) 0.4621(2) 0.21515(12) 0.0208(3) Uani 1 1 d . . .
C2 C 0.95942(19) 0.5230(2) 0.14708(11) 0.0182(3) Uani 1 1 d . . .
C3 C 0.9759(2) 0.5305(2) 0.03277(12) 0.0205(3) Uani 1 1 d . . .
H3 H 1.0774 0.4931 0.0018 0.025 Uiso 1 1 calc R . .
C4 C 0.8448(2) 0.5917(2) -0.03235(11) 0.0208(4) Uani 1 1 d . . .
H4 H 0.8572 0.6003 -0.1085 0.025 Uiso 1 1 calc R . .
C5 C 0.6907(2) 0.6425(2) 0.01269(11) 0.0182(3) Uani 1 1 d . . .
C6 C 0.5498(2) 0.6966(2) -0.05495(12) 0.0225(4) Uani 1 1 d . . .
H6 H 0.5604 0.7040 -0.1313 0.027 Uiso 1 1 calc R . .
C7 C 0.3991(2) 0.7382(3) -0.01088(13) 0.0235(4) Uani 1 1 d . . .
H7 H 0.3048 0.7709 -0.0571 0.028 Uiso 1 1 calc R . .
C8 C 0.3826(2) 0.7328(3) 0.10283(13) 0.0234(4) Uani 1 1 d . . .
H8 H 0.2782 0.7645 0.1325 0.028 Uiso 1 1 calc R . .
C9 C 0.5161(2) 0.6824(2) 0.17074(12) 0.0204(3) Uani 1 1 d . . .
H9 H 0.5037 0.6795 0.2471 0.024 Uiso 1 1 calc R . .
C10 C 0.67302(19) 0.6343(2) 0.12715(11) 0.0173(3) Uani 1 1 d . . .
C11 C 0.81282(19) 0.5760(2) 0.19527(11) 0.0167(3) Uani 1 1 d . . .
C12 C 0.80644(18) 0.5868(2) 0.31586(11) 0.0173(3) Uani 1 1 d . . .
C13 C 0.75134(18) 0.4514(2) 0.38050(11) 0.0179(3) Uani 1 1 d . . .
C14 C 0.6979(2) 0.2950(2) 0.33508(12) 0.0214(3) Uani 1 1 d . . .
H14 H 0.6987 0.2785 0.2587 0.026 Uiso 1 1 calc R . .
C15 C 0.6451(2) 0.1679(3) 0.40040(14) 0.0251(4) Uani 1 1 d . . .
H15 H 0.6081 0.0648 0.3688 0.030 Uiso 1 1 calc R . .
C16 C 0.6451(2) 0.1888(3) 0.51433(13) 0.0255(4) Uani 1 1 d . . .
H16 H 0.6101 0.0992 0.5589 0.031 Uiso 1 1 calc R . .
C17 C 0.6953(2) 0.3373(2) 0.56056(12) 0.0230(4) Uani 1 1 d . . .
H17 H 0.6945 0.3501 0.6372 0.028 Uiso 1 1 calc R . .
C18 C 0.74892(19) 0.4730(2) 0.49575(12) 0.0190(3) Uani 1 1 d . . .
C19 C 0.79859(19) 0.6284(3) 0.54301(12) 0.0219(4) Uani 1 1 d . . .
H19 H 0.7957 0.6426 0.6195 0.026 Uiso 1 1 calc R . .
C20 C 0.8507(2) 0.7583(2) 0.48024(12) 0.0216(4) Uani 1 1 d . . .
H20 H 0.8838 0.8621 0.5126 0.026 Uiso 1 1 calc R . .
C21 C 0.85456(19) 0.7358(2) 0.36560(12) 0.0193(3) Uani 1 1 d . . .
C22 C 0.9096(2) 0.8722(2) 0.29852(12) 0.0233(4) Uani 1 1 d . . .
N1 N 1.21616(17) 0.4159(2) 0.26742(11) 0.0279(3) Uani 1 1 d . . .
N2 N 0.9519(2) 0.9792(2) 0.24420(13) 0.0324(4) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 N1 1.149(2) . ?
C1 C2 1.446(2) . ?
C2 C11 1.389(2) . ?
C2 C3 1.4214(18) . ?
C3 C4 1.367(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.417(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.423(2) . ?
C5 C10 1.4247(18) . ?
C6 C7 1.369(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.413(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.372(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.423(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.4299(19) . ?
C11 C12 1.4910(18) . ?
C12 C21 1.382(2) . ?
C12 C13 1.422(2) . ?
C13 C14 1.423(3) . ?
C13 C18 1.4310(18) . ?
C14 C15 1.371(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.413(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.365(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.421(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.417(3) . ?
C19 C20 1.367(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.4253(19) . ?
C20 H20 0.9500 . ?
C21 C22 1.445(2) . ?
C22 N2 1.144(2) . ?

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
N1 C1 C2 178.13(17) . . ?
C11 C2 C3 121.84(13) . . ?
C11 C2 C1 119.15(13) . . ?
C3 C2 C1 118.99(13) . . ?
C4 C3 C2 119.63(14) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.61(13) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 121.07(13) . . ?
C4 C5 C10 120.00(13) . . ?
C6 C5 C10 118.90(14) . . ?
C7 C6 C5 120.53(14) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.49(14) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.63(15) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.19(13) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 119.24(13) . . ?
C9 C10 C11 121.62(12) . . ?
C5 C10 C11 119.14(13) . . ?
C2 C11 C10 118.72(13) . . ?
C2 C11 C12 120.76(13) . . ?
C10 C11 C12 120.29(13) . . ?
C21 C12 C13 119.32(13) . . ?
C21 C12 C11 118.03(14) . . ?
C13 C12 C11 122.65(14) . . ?
C12 C13 C14 122.57(13) . . ?
C12 C13 C18 118.89(15) . . ?
C14 C13 C18 118.54(15) . . ?
C15 C14 C13 120.67(15) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.64(18) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 120.21(17) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.98(15) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 121.30(14) . . ?
C19 C18 C13 119.75(15) . . ?
C17 C18 C13 118.95(15) . . ?
C20 C19 C18 121.01(14) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 119.07(16) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C12 C21 C20 121.95(15) . . ?
C12 C21 C22 118.52(13) . . ?
C20 C21 C22 119.52(16) . . ?
N2 C22 C21 179.05(18) . . ?

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
N1 C1 C2 C11 -142(6) . . . . ?
N1 C1 C2 C3 37(6) . . . . ?
C11 C2 C3 C4 0.2(3) . . . . ?
C1 C2 C3 C4 -178.37(17) . . . . ?
C2 C3 C4 C5 -2.2(3) . . . . ?
C3 C4 C5 C6 -176.08(17) . . . . ?
C3 C4 C5 C10 1.8(3) . . . . ?
C4 C5 C6 C7 177.06(18) . . . . ?
C10 C5 C6 C7 -0.8(3) . . . . ?
C5 C6 C7 C8 1.9(3) . . . . ?
C6 C7 C8 C9 -1.5(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C5 1.2(3) . . . . ?
C8 C9 C10 C11 -177.97(17) . . . . ?
C4 C5 C10 C9 -178.67(18) . . . . ?
C6 C5 C10 C9 -0.8(2) . . . . ?
C4 C5 C10 C11 0.6(2) . . . . ?
C6 C5 C10 C11 178.46(17) . . . . ?
C3 C2 C11 C10 2.1(3) . . . . ?
C1 C2 C11 C10 -179.32(16) . . . . ?
C3 C2 C11 C12 -172.38(16) . . . . ?
C1 C2 C11 C12 6.2(3) . . . . ?
C9 C10 C11 C2 176.78(16) . . . . ?
C5 C10 C11 C2 -2.4(2) . . . . ?
C9 C10 C11 C12 -8.7(3) . . . . ?
C5 C10 C11 C12 172.07(15) . . . . ?
C2 C11 C12 C21 89.6(2) . . . . ?
C10 C11 C12 C21 -84.78(19) . . . . ?
C2 C11 C12 C13 -91.13(19) . . . . ?
C10 C11 C12 C13 94.48(19) . . . . ?
C21 C12 C13 C14 179.21(14) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C21 C12 C13 C18 -0.6(2) . . . . ?
C11 C12 C13 C18 -179.86(13) . . . . ?
C12 C13 C14 C15 -179.76(14) . . . . ?
C18 C13 C14 C15 0.1(2) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C14 C15 C16 C17 1.1(2) . . . . ?
C15 C16 C17 C18 -0.3(2) . . . . ?
C16 C17 C18 C19 178.96(15) . . . . ?
C16 C17 C18 C13 -0.6(2) . . . . ?
C12 C13 C18 C19 0.9(2) . . . . ?
C14 C13 C18 C19 -178.87(15) . . . . ?
C12 C13 C18 C17 -179.44(14) . . . . ?
C14 C13 C18 C17 0.7(2) . . . . ?
C17 C18 C19 C20 179.74(14) . . . . ?
C13 C18 C19 C20 -0.7(2) . . . . ?
C18 C19 C20 C21 0.0(2) . . . . ?
C13 C12 C21 C20 0.0(2) . . . . ?
C11 C12 C21 C20 179.26(14) . . . . ?
C13 C12 C21 C22 -179.77(13) . . . . ?
C11 C12 C21 C22 -0.5(2) . . . . ?
C19 C20 C21 C12 0.3(2) . . . . ?
C19 C20 C21 C22 -179.93(16) . . . . ?
C12 C21 C22 N2 22(12) . . . . ?
C20 C21 C22 N2 -158(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.855
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_hg427150_0m
_database_code_depnum_ccdc_archive 'CCDC 1061957'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H23 O P'
_chemical_formula_weight         406.43
_chemical_absolute_configuration ad

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   7.9622(4)
_cell_length_b                   12.3209(7)
_cell_length_c                   21.0198(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2062.07(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7714
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      36.84

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9895
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_suppport 
'magnetic support whith 10 micron nylon fiber cryoloop'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_type              'Bruker-Nonius FR 591'
_diffrn_source_power             50
_diffrn_source_current           70
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            22768
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         38.03
_reflns_number_total             10895
_reflns_number_gt                9504
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 v2009.1-0'
_computing_cell_refinement       'Bruker APEX2 v2009.1-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0618P)²+0.0239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_number_reflns         10895
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.26344(11) 0.84535(9) 0.13143(4) 0.01543(14) Uani 1 1 d . . .
H1A H -0.2055 0.7766 0.1208 0.019 Uiso 1 1 calc R . .
H1B H -0.3695 0.8482 0.1069 0.019 Uiso 1 1 calc R . .
C2 C -0.15378(11) 0.93992(8) 0.11305(4) 0.01370(14) Uani 1 1 d . . .
C3 C -0.22437(12) 1.02840(9) 0.07878(4) 0.01698(16) Uani 1 1 d . . .
H3 H -0.3380 1.0247 0.0651 0.020 Uiso 1 1 calc R . .
C4 C -0.13085(12) 1.11892(9) 0.06514(4) 0.01715(16) Uani 1 1 d . . .
H4 H -0.1793 1.1761 0.0410 0.021 Uiso 1 1 calc R . .
C5 C 0.03791(12) 1.12812(8) 0.08668(4) 0.01457(15) Uani 1 1 d . . .
C6 C 0.13099(13) 1.22520(9) 0.07805(5) 0.01838(17) Uani 1 1 d . . .
H6 H 0.0822 1.2842 0.0556 0.022 Uiso 1 1 calc R . .
C7 C 0.29102(13) 1.23472(9) 0.10183(5) 0.02019(17) Uani 1 1 d . . .
H7 H 0.3523 1.3001 0.0958 0.024 Uiso 1 1 calc R . .
C8 C 0.36439(12) 1.14699(9) 0.13530(5) 0.01794(16) Uani 1 1 d . . .
H8 H 0.4747 1.1542 0.1520 0.022 Uiso 1 1 calc R . .
C9 C 0.27805(11) 1.05131(8) 0.14395(4) 0.01501(15) Uani 1 1 d . . .
H9 H 0.3300 0.9929 0.1659 0.018 Uiso 1 1 calc R . .
C10 C 0.11136(11) 1.03923(7) 0.12026(4) 0.01259(13) Uani 1 1 d . . .
C11 C 0.01379(11) 0.94303(8) 0.13127(4) 0.01229(13) Uani 1 1 d . . .
C12 C 0.08945(10) 0.84863(8) 0.16518(4) 0.01228(13) Uani 1 1 d . . .
C13 C 0.21551(10) 0.78340(8) 0.13481(4) 0.01287(13) Uani 1 1 d . . .
C14 C 0.26294(11) 0.79898(8) 0.07009(4) 0.01508(15) Uani 1 1 d . . .
H14 H 0.2175 0.8581 0.0467 0.018 Uiso 1 1 calc R . .
C15 C 0.37403(12) 0.72909(9) 0.04110(5) 0.01857(16) Uani 1 1 d . . .
H15 H 0.4026 0.7396 -0.0023 0.022 Uiso 1 1 calc R . .
C16 C 0.44617(13) 0.64163(9) 0.07527(5) 0.02127(18) Uani 1 1 d . . .
H16 H 0.5229 0.5939 0.0548 0.026 Uiso 1 1 calc R . .
C17 C 0.40488(12) 0.62603(9) 0.13798(5) 0.01919(17) Uani 1 1 d . . .
H17 H 0.4545 0.5679 0.1609 0.023 Uiso 1 1 calc R . .
C18 C 0.28890(11) 0.69576(8) 0.16898(4) 0.01451(14) Uani 1 1 d . . .
C19 C 0.23883(12) 0.67573(8) 0.23282(5) 0.01625(15) Uani 1 1 d . . .
H19 H 0.2937 0.6211 0.2570 0.019 Uiso 1 1 calc R . .
C20 C 0.11159(12) 0.73510(8) 0.25957(4) 0.01571(15) Uani 1 1 d . . .
H20 H 0.0750 0.7186 0.3015 0.019 Uiso 1 1 calc R . .
C21 C 0.03365(11) 0.82106(8) 0.22548(4) 0.01353(14) Uani 1 1 d . . .
C22 C -0.11241(11) 0.88127(9) 0.25466(4) 0.01516(15) Uani 1 1 d . . .
H22A H -0.0922 0.9603 0.2511 0.018 Uiso 1 1 calc R . .
H22B H -0.1196 0.8630 0.3004 0.018 Uiso 1 1 calc R . .
O1 O -0.44976(10) 0.92208(8) 0.23551(4) 0.02281(16) Uani 1 1 d . . .
P1 P -0.31057(3) 0.84837(2) 0.216538(11) 0.01536(5) Uani 1 1 d . . .
H1P H -0.345(2) 0.7506(18) 0.2325(8) 0.037(5) Uiso 1 1 d . . .
C1A C 0.91141(13) 0.55397(10) 0.13322(5) 0.02257(19) Uani 1 1 d . . .
H1A1 H 0.9769 0.6076 0.1542 0.027 Uiso 1 1 calc R . .
C2A C 0.93598(13) 0.53359(10) 0.06857(5) 0.02250(19) Uani 1 1 d . . .
H2A H 1.0192 0.5725 0.0456 0.027 Uiso 1 1 calc R . .
C3A C 0.83827(13) 0.45628(10) 0.03803(5) 0.02085(18) Uani 1 1 d . . .
H3A H 0.8538 0.4428 -0.0061 0.025 Uiso 1 1 calc R . .
C4A C 0.71735(13) 0.39822(9) 0.07187(5) 0.01953(17) Uani 1 1 d . . .
H4A H 0.6501 0.3457 0.0507 0.023 Uiso 1 1 calc R . .
C5A C 0.69511(13) 0.41714(9) 0.13664(5) 0.01906(16) Uani 1 1 d . . .
H5A H 0.6147 0.3764 0.1600 0.023 Uiso 1 1 calc R . .
C6A C 0.79113(13) 0.49583(10) 0.16699(5) 0.02063(18) Uani 1 1 d . . .
H6A H 0.7745 0.5100 0.2110 0.025 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.5065(14) . ?
C1 P1 1.8282(9) . ?
C2 C11 1.3886(12) . ?
C2 C3 1.4224(13) . ?
C3 C4 1.3714(15) . ?
C4 C5 1.4225(13) . ?
C5 C6 1.4187(14) . ?
C5 C10 1.4282(13) . ?
C6 C7 1.3737(15) . ?
C7 C8 1.4159(15) . ?
C8 C9 1.3768(14) . ?
C9 C10 1.4254(12) . ?
C10 C11 1.4360(13) . ?
C11 C12 1.4912(12) . ?
C12 C21 1.3854(12) . ?
C12 C13 1.4356(12) . ?
C13 C18 1.4224(13) . ?
C13 C14 1.4248(13) . ?
C14 C15 1.3767(13) . ?
C15 C16 1.4168(15) . ?
C16 C17 1.3720(15) . ?
C17 C18 1.4196(13) . ?
C18 C19 1.4216(13) . ?
C19 C20 1.3703(14) . ?
C20 C21 1.4213(13) . ?
C21 C22 1.5097(13) . ?
C22 P1 1.8155(9) . ?
O1 P1 1.4873(8) . ?
C1A C6A 1.3907(16) . ?
C1A C2A 1.3957(16) . ?
C2A C3A 1.3874(16) . ?
C3A C4A 1.3945(15) . ?
C4A C5A 1.3925(15) . ?
C5A C6A 1.3898(16) . ?

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
C2 C1 P1 110.74(6) . . ?
C11 C2 C3 119.88(9) . . ?
C11 C2 C1 120.49(8) . . ?
C3 C2 C1 119.58(8) . . ?
C4 C3 C2 120.97(9) . . ?
C3 C4 C5 120.74(9) . . ?
C6 C5 C4 121.33(9) . . ?
C6 C5 C10 119.72(9) . . ?
C4 C5 C10 118.88(9) . . ?
C7 C6 C5 120.67(9) . . ?
C6 C7 C8 119.89(10) . . ?
C9 C8 C7 120.89(9) . . ?
C8 C9 C10 120.54(9) . . ?
C9 C10 C5 118.28(8) . . ?
C9 C10 C11 122.25(8) . . ?
C5 C10 C11 119.41(8) . . ?
C2 C11 C10 119.88(8) . . ?
C2 C11 C12 119.90(8) . . ?
C10 C11 C12 120.15(7) . . ?
C21 C12 C13 119.59(8) . . ?
C21 C12 C11 119.93(8) . . ?
C13 C12 C11 120.44(7) . . ?
C18 C13 C14 118.39(8) . . ?
C18 C13 C12 119.19(8) . . ?
C14 C13 C12 122.31(8) . . ?
C15 C14 C13 120.57(9) . . ?
C14 C15 C16 120.79(9) . . ?
C17 C16 C15 119.77(9) . . ?
C16 C17 C18 120.80(9) . . ?
C17 C18 C19 120.71(9) . . ?
C17 C18 C13 119.67(8) . . ?
C19 C18 C13 119.55(8) . . ?
C20 C19 C18 120.14(8) . . ?
C19 C20 C21 120.91(8) . . ?
C12 C21 C20 120.26(8) . . ?
C12 C21 C22 119.89(8) . . ?
C20 C21 C22 119.84(8) . . ?
C21 C22 P1 112.36(6) . . ?
O1 P1 C22 113.14(5) . . ?
O1 P1 C1 115.32(5) . . ?
C22 P1 C1 104.96(4) . . ?
C6A C1A C2A 120.06(10) . . ?
C3A C2A C1A 119.70(10) . . ?
C2A C3A C4A 120.21(9) . . ?
C5A C4A C3A 120.05(10) . . ?
C6A C5A C4A 119.71(10) . . ?
C5A C6A C1A 120.25(9) . . ?

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
P1 C1 C2 C11 71.71(10) . . . . ?
P1 C1 C2 C3 -105.99(8) . . . . ?
C11 C2 C3 C4 -2.20(14) . . . . ?
C1 C2 C3 C4 175.51(9) . . . . ?
C2 C3 C4 C5 -1.99(14) . . . . ?
C3 C4 C5 C6 -174.09(9) . . . . ?
C3 C4 C5 C10 2.94(13) . . . . ?
C4 C5 C6 C7 176.82(9) . . . . ?
C10 C5 C6 C7 -0.18(14) . . . . ?
C5 C6 C7 C8 0.02(14) . . . . ?
C6 C7 C8 C9 0.61(15) . . . . ?
C7 C8 C9 C10 -1.08(14) . . . . ?
C8 C9 C10 C5 0.90(13) . . . . ?
C8 C9 C10 C11 -176.54(9) . . . . ?
C6 C5 C10 C9 -0.27(12) . . . . ?
C4 C5 C10 C9 -177.35(8) . . . . ?
C6 C5 C10 C11 177.24(8) . . . . ?
C4 C5 C10 C11 0.17(12) . . . . ?
C3 C2 C11 C10 5.29(13) . . . . ?
C1 C2 C11 C10 -172.40(8) . . . . ?
C3 C2 C11 C12 -177.83(8) . . . . ?
C1 C2 C11 C12 4.48(12) . . . . ?
C9 C10 C11 C2 173.14(8) . . . . ?
C5 C10 C11 C2 -4.27(12) . . . . ?
C9 C10 C11 C12 -3.73(12) . . . . ?
C5 C10 C11 C12 178.86(8) . . . . ?
C2 C11 C12 C21 -65.53(11) . . . . ?
C10 C11 C12 C21 111.35(10) . . . . ?
C2 C11 C12 C13 112.10(10) . . . . ?
C10 C11 C12 C13 -71.03(11) . . . . ?
C21 C12 C13 C18 -4.16(13) . . . . ?
C11 C12 C13 C18 178.21(8) . . . . ?
C21 C12 C13 C14 171.91(8) . . . . ?
C11 C12 C13 C14 -5.73(13) . . . . ?
C18 C13 C14 C15 1.56(14) . . . . ?
C12 C13 C14 C15 -174.53(9) . . . . ?
C13 C14 C15 C16 -1.32(15) . . . . ?
C14 C15 C16 C17 0.13(16) . . . . ?
C15 C16 C17 C18 0.78(16) . . . . ?
C16 C17 C18 C19 176.31(10) . . . . ?
C16 C17 C18 C13 -0.50(15) . . . . ?
C14 C13 C18 C17 -0.66(13) . . . . ?
C12 C13 C18 C17 175.55(9) . . . . ?
C14 C13 C18 C19 -177.51(8) . . . . ?
C12 C13 C18 C19 -1.29(13) . . . . ?
C17 C18 C19 C20 -171.79(9) . . . . ?
C13 C18 C19 C20 5.02(14) . . . . ?
C18 C19 C20 C21 -3.32(14) . . . . ?
C13 C12 C21 C20 5.95(13) . . . . ?
C11 C12 C21 C20 -176.41(8) . . . . ?
C13 C12 C21 C22 -173.02(8) . . . . ?
C11 C12 C21 C22 4.63(13) . . . . ?
C19 C20 C21 C12 -2.24(14) . . . . ?
C19 C20 C21 C22 176.73(9) . . . . ?
C12 C21 C22 P1 71.08(10) . . . . ?
C20 C21 C22 P1 -107.89(8) . . . . ?
C21 C22 P1 O1 -168.56(7) . . . . ?
C21 C22 P1 C1 -42.01(8) . . . . ?
C2 C1 P1 O1 81.62(8) . . . . ?
C2 C1 P1 C22 -43.58(8) . . . . ?
C6A C1A C2A C3A 0.93(17) . . . . ?
C1A C2A C3A C4A -0.75(16) . . . . ?
C2A C3A C4A C5A -0.46(16) . . . . ?
C3A C4A C5A C6A 1.50(15) . . . . ?
C4A C5A C6A C1A -1.33(15) . . . . ?
C2A C1A C6A C5A 0.11(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        38.03
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_hg483_0m
_database_code_depnum_ccdc_archive 'CCDC 1062002'
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 Br N O'
_chemical_formula_weight         200.04

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   4.9200(7)
_cell_length_b                   5.3316(8)
_cell_length_c                   27.538(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.562(6)
_cell_angle_gamma                90.00
_cell_volume                     720.97(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6932
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      35.02

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    5.624
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4360
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_suppport 
'magnetic support whith 10 micron nylon fiber cryoloop'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_type              'Bruker-Nonius FR 591'
_diffrn_source_power             50
_diffrn_source_current           70
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            13597
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         35.18
_reflns_number_total             3157
_reflns_number_gt                2791
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 v2009.1-0'
_computing_cell_refinement       'Bruker APEX2 v2009.1-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0596P)²+0.0843P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3157
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.38757(4) -0.05958(3) 0.210942(6) 0.02326(8) Uani 1 1 d . . .
C1 C 0.2771(3) 0.1731(3) 0.16151(6) 0.0165(2) Uani 1 1 d . . .
C4 C 0.1333(3) 0.5191(3) 0.08930(5) 0.0131(2) Uani 1 1 d . . .
C2 C 0.0686(3) 0.3408(3) 0.16854(6) 0.0201(3) Uani 1 1 d . . .
H2 H -0.0229 0.3392 0.1979 0.024 Uiso 1 1 calc R . .
C5 C 0.3421(3) 0.3460(3) 0.08321(6) 0.0173(3) Uani 1 1 d . . .
H5 H 0.4359 0.3483 0.0541 0.021 Uiso 1 1 calc R . .
C6 C 0.4144(3) 0.1709(3) 0.11894(6) 0.0185(3) Uani 1 1 d . . .
H6 H 0.5547 0.0523 0.1144 0.022 Uiso 1 1 calc R . .
C3 C -0.0051(3) 0.5126(3) 0.13174(6) 0.0179(3) Uani 1 1 d . . .
H3 H -0.1510 0.6258 0.1358 0.022 Uiso 1 1 calc R . .
C7 C 0.0579(2) 0.7103(2) 0.05129(5) 0.0131(2) Uani 1 1 d . . .
O1 O -0.1748(2) 0.8028(2) 0.04719(5) 0.0178(2) Uani 1 1 d . . .
N1 N 0.2529(2) 0.7758(2) 0.02176(5) 0.0156(2) Uani 1 1 d . . .
H1A H 0.2181 0.8873 -0.0014 0.019 Uiso 1 1 calc R . .
H1B H 0.4156 0.7073 0.0255 0.019 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
Br1 C1 1.8961(15) . ?
C1 C2 1.384(2) . ?
C1 C6 1.389(2) . ?
C4 C3 1.389(2) . ?
C4 C5 1.3986(19) . ?
C4 C7 1.491(2) . ?
C2 C3 1.397(2) . ?
C5 C6 1.386(2) . ?
C7 O1 1.2454(15) . ?
C7 N1 1.3419(17) . ?

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
C2 C1 C6 121.82(14) . . ?
C2 C1 Br1 120.29(12) . . ?
C6 C1 Br1 117.88(11) . . ?
C3 C4 C5 119.09(14) . . ?
C3 C4 C7 119.61(12) . . ?
C5 C4 C7 121.31(12) . . ?
C1 C2 C3 118.91(14) . . ?
C6 C5 C4 121.16(13) . . ?
C5 C6 C1 118.45(13) . . ?
C4 C3 C2 120.54(14) . . ?
O1 C7 N1 121.99(14) . . ?
O1 C7 C4 121.44(12) . . ?
N1 C7 C4 116.57(11) . . ?

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 0.0(2) . . . . ?
Br1 C1 C2 C3 178.97(12) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C7 C4 C5 C6 179.01(14) . . . . ?
C4 C5 C6 C1 -0.9(2) . . . . ?
C2 C1 C6 C5 1.3(2) . . . . ?
Br1 C1 C6 C5 -177.76(12) . . . . ?
C5 C4 C3 C2 2.0(2) . . . . ?
C7 C4 C3 C2 -177.75(14) . . . . ?
C1 C2 C3 C4 -1.6(2) . . . . ?
C3 C4 C7 O1 -25.9(2) . . . . ?
C5 C4 C7 O1 154.37(15) . . . . ?
C3 C4 C7 N1 154.48(15) . . . . ?
C5 C4 C7 N1 -25.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        35.18
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         1.820
_refine_diff_density_min         -1.372
_refine_diff_density_rms         0.171
