# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_CmpF_[10-131]
_database_code_depnum_ccdc_archive 'CCDC 1829148'
loop_
_audit_author_name
_audit_author_address
'John Gallagher'
;Dublin City University
Republic of Ireland
;
_audit_update_record             
;
2018-03-12 deposited with the CCDC.	2019-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4-Fluorobenzene-N-3-pyridylcarbamate
_chemical_name_common            CmpF
_chemical_melting_point          439
_chemical_formula_moiety         'C12 H9 F N2 O2'
_chemical_formula_sum            'C12 H9 F N2 O2'
_chemical_formula_weight         232.21

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.1578(3)
_cell_length_b                   3.7938(1)
_cell_length_c                   23.0837(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.103(2)
_cell_angle_gamma                90
_cell_volume                     1060.50(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    3930
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.47

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         7632
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_diffrn_detector_area_resol_mean 16.056
_diffrn_reflns_number            6916
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.332
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.732
_diffrn_reflns_point_group_measured_fraction_full 0.756
_reflns_number_total             3554
_reflns_number_gt                3158
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.513
_reflns_Friedel_fraction_max     0.496
_reflns_Friedel_fraction_full    0.518

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7
_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)+(0.0558P)²+0.0725P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x from 917 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack & Wagner, 2013).
;
_refine_ls_abs_structure_Flack   0.2(10)
_chemical_absolute_configuration unknown
_refine_ls_number_reflns         3554
_refine_ls_number_parameters     315
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.034

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
F14A F 0.45994(19) 0.6289(8) 0.10451(12) 0.0824(8) Uani 1 1 d . . . . .
O1A O 0.03432(17) 0.4292(6) 0.21959(9) 0.0451(6) Uani 1 1 d . . . . .
O2A O 0.02062(16) 0.7356(6) 0.13479(8) 0.0440(5) Uani 1 1 d . . . . .
C1A C -0.0204(2) 0.5902(8) 0.18241(11) 0.0349(6) Uani 1 1 d . . . . .
N1A N -0.1298(2) 0.6545(8) 0.17976(10) 0.0398(6) Uani 1 1 d . . . . .
H1A H -0.158(3) 0.756(9) 0.1516(14) 0.036(9) Uiso 1 1 d . . . . .
C11A C 0.1336(2) 0.7006(8) 0.12948(11) 0.0360(6) Uani 1 1 d . . . . .
C12A C 0.2106(2) 0.8415(8) 0.17041(12) 0.0392(6) Uani 1 1 d . . . . .
H12A H 0.1882 0.9529 0.2033 0.047 Uiso 1 1 calc R U . . .
C13A C 0.3213(3) 0.8155(9) 0.16215(14) 0.0451(7) Uani 1 1 d . . . . .
H13A H 0.3748 0.9060 0.1895 0.054 Uiso 1 1 calc R U . . .
C14A C 0.3508(3) 0.6527(9) 0.11262(16) 0.0498(8) Uani 1 1 d . . . . .
C15A C 0.2754(3) 0.5159(9) 0.07155(14) 0.0492(8) Uani 1 1 d . . . . .
H15A H 0.2982 0.4094 0.0383 0.059 Uiso 1 1 calc R U . . .
C16A C 0.1641(3) 0.5378(9) 0.08000(12) 0.0430(7) Uani 1 1 d . . . . .
H16A H 0.1110 0.4443 0.0528 0.052 Uiso 1 1 calc R U . . .
C21A C -0.2018(2) 0.5465(8) 0.22063(12) 0.0344(6) Uani 1 1 d . . . . .
C22A C -0.1667(3) 0.4192(9) 0.27582(12) 0.0432(7) Uani 1 1 d . . . . .
H22A H -0.0912 0.4003 0.2862 0.052 Uiso 1 1 calc R U . . .
N23A N -0.2365(2) 0.3233(8) 0.31440(11) 0.0462(6) Uani 1 1 d . . . . .
C24A C -0.3438(3) 0.3552(9) 0.29966(14) 0.0474(8) Uani 1 1 d . . . . .
H24A H -0.3929 0.2925 0.3266 0.057 Uiso 1 1 calc R U . . .
C25A C -0.3853(3) 0.4775(10) 0.24621(14) 0.0509(8) Uani 1 1 d . . . . .
H25A H -0.4611 0.4939 0.2371 0.061 Uiso 1 1 calc R U . . .
C26A C -0.3137(3) 0.5754(9) 0.20625(13) 0.0438(7) Uani 1 1 d . . . . .
H26A H -0.3406 0.6602 0.1699 0.053 Uiso 1 1 calc R U . . .
F14B F 0.46276(18) 1.1617(8) -0.13332(11) 0.0829(8) Uani 1 1 d . . . . .
O1B O 0.0228(2) 1.1933(7) -0.02920(10) 0.0581(7) Uani 1 1 d . . . . .
O2B O 0.02222(18) 0.9374(7) -0.11796(9) 0.0480(6) Uani 1 1 d . . . . .
C1B C -0.0256(3) 1.0415(9) -0.06951(12) 0.0412(7) Uani 1 1 d . . . . .
N1B N -0.1327(2) 0.9566(8) -0.07512(11) 0.0418(6) Uani 1 1 d . . . . .
H1B H -0.160(3) 0.880(10) -0.1045(15) 0.045(10) Uiso 1 1 d . . . . .
C11B C 0.1352(2) 1.0002(9) -0.11929(12) 0.0394(7) Uani 1 1 d . . . . .
C12B C 0.2113(3) 0.8844(9) -0.07565(13) 0.0452(7) Uani 1 1 d . . . . .
H12B H 0.1880 0.7700 -0.0433 0.054 Uiso 1 1 calc R U . . .
C13B C 0.3219(3) 0.9395(10) -0.08038(14) 0.0509(8) Uani 1 1 d . . . . .
H13B H 0.3744 0.8653 -0.0512 0.061 Uiso 1 1 calc R U . . .
C14B C 0.3532(3) 1.1058(10) -0.12894(15) 0.0512(8) Uani 1 1 d . . . . .
C15B C 0.2789(3) 1.2160(10) -0.17281(14) 0.0508(8) Uani 1 1 d . . . . .
H15B H 0.3028 1.3249 -0.2055 0.061 Uiso 1 1 calc R U . . .
C16B C 0.1678(3) 1.1644(9) -0.16817(12) 0.0456(7) Uani 1 1 d . . . . .
H16B H 0.1157 1.2392 -0.1975 0.055 Uiso 1 1 calc R U . . .
C21B C -0.2034(2) 1.0158(8) -0.03098(12) 0.0363(6) Uani 1 1 d . . . . .
C22B C -0.1692(3) 0.9369(9) 0.02680(12) 0.0413(7) Uani 1 1 d . . . . .
H22B H -0.0985 0.8475 0.0355 0.050 Uiso 1 1 calc R U . . .
N23B N -0.2334(2) 0.9841(8) 0.07010(10) 0.0461(6) Uani 1 1 d . . . . .
C24B C -0.3344(3) 1.1117(9) 0.05681(14) 0.0468(8) Uani 1 1 d . . . . .
H24B H -0.3798 1.1470 0.0867 0.056 Uiso 1 1 calc R U . . .
C25B C -0.3749(3) 1.1940(9) 0.00083(14) 0.0481(8) Uani 1 1 d . . . . .
H25B H -0.4462 1.2816 -0.0068 0.058 Uiso 1 1 calc R U . . .
C26B C -0.3080(3) 1.1442(9) -0.04362(13) 0.0437(7) Uani 1 1 d . . . . .
H26B H -0.3336 1.1973 -0.0818 0.052 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
F14A C14A 1.359(4) . ?
O1A C1A 1.204(3) . ?
O2A C1A 1.363(3) . ?
O2A C11A 1.397(3) . ?
C1A N1A 1.348(4) . ?
N1A C21A 1.404(4) . ?
N1A H1A 0.80(3) . ?
C11A C12A 1.377(4) . ?
C11A C16A 1.378(4) . ?
C12A C13A 1.380(4) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.375(5) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.362(5) . ?
C15A C16A 1.386(5) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C21A C26A 1.376(4) . ?
C21A C22A 1.393(4) . ?
C22A N23A 1.335(4) . ?
C22A H22A 0.9300 . ?
N23A C24A 1.324(4) . ?
C24A C25A 1.371(5) . ?
C24A H24A 0.9300 . ?
C25A C26A 1.374(4) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
F14B C14B 1.361(4) . ?
O1B C1B 1.203(4) . ?
O2B C1B 1.364(3) . ?
O2B C11B 1.398(4) . ?
C1B N1B 1.336(4) . ?
N1B C21B 1.408(4) . ?
N1B H1B 0.79(4) . ?
C11B C12B 1.377(4) . ?
C11B C16B 1.378(4) . ?
C12B C13B 1.375(5) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.369(5) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.362(5) . ?
C15B C16B 1.378(5) . ?
C15B H15B 0.9300 . ?
C16B H16B 0.9300 . ?
C21B C26B 1.368(4) . ?
C21B C22B 1.394(4) . ?
C22B N23B 1.334(4) . ?
C22B H22B 0.9300 . ?
N23B C24B 1.330(4) . ?
C24B C25B 1.377(5) . ?
C24B H24B 0.9300 . ?
C25B C26B 1.378(5) . ?
C25B H25B 0.9300 . ?
C26B H26B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A O2A C11A 117.8(2) . . ?
O1A C1A N1A 127.2(3) . . ?
O1A C1A O2A 124.1(3) . . ?
N1A C1A O2A 108.7(2) . . ?
C1A N1A C21A 126.0(2) . . ?
C1A N1A H1A 118(2) . . ?
C21A N1A H1A 116(2) . . ?
C12A C11A C16A 121.7(3) . . ?
C12A C11A O2A 121.1(3) . . ?
C16A C11A O2A 117.0(3) . . ?
C11A C12A C13A 119.3(3) . . ?
C11A C12A H12A 120.4 . . ?
C13A C12A H12A 120.4 . . ?
C14A C13A C12A 118.5(3) . . ?
C14A C13A H13A 120.8 . . ?
C12A C13A H13A 120.8 . . ?
F14A C14A C15A 119.0(3) . . ?
F14A C14A C13A 118.3(3) . . ?
C15A C14A C13A 122.7(3) . . ?
C14A C15A C16A 119.0(3) . . ?
C14A C15A H15A 120.5 . . ?
C16A C15A H15A 120.5 . . ?
C11A C16A C15A 118.8(3) . . ?
C11A C16A H16A 120.6 . . ?
C15A C16A H16A 120.6 . . ?
C26A C21A C22A 117.7(3) . . ?
C26A C21A N1A 118.5(2) . . ?
C22A C21A N1A 123.8(3) . . ?
N23A C22A C21A 122.9(3) . . ?
N23A C22A H22A 118.6 . . ?
C21A C22A H22A 118.6 . . ?
C24A N23A C22A 118.3(3) . . ?
N23A C24A C25A 122.5(3) . . ?
N23A C24A H24A 118.8 . . ?
C25A C24A H24A 118.8 . . ?
C24A C25A C26A 119.4(3) . . ?
C24A C25A H25A 120.3 . . ?
C26A C25A H25A 120.3 . . ?
C25A C26A C21A 119.2(3) . . ?
C25A C26A H26A 120.4 . . ?
C21A C26A H26A 120.4 . . ?
C1B O2B C11B 117.4(2) . . ?
O1B C1B N1B 126.6(3) . . ?
O1B C1B O2B 123.9(3) . . ?
N1B C1B O2B 109.5(2) . . ?
C1B N1B C21B 122.9(2) . . ?
C1B N1B H1B 121(2) . . ?
C21B N1B H1B 116(3) . . ?
C12B C11B C16B 121.3(3) . . ?
C12B C11B O2B 121.8(3) . . ?
C16B C11B O2B 116.7(3) . . ?
C13B C12B C11B 119.4(3) . . ?
C13B C12B H12B 120.3 . . ?
C11B C12B H12B 120.3 . . ?
C14B C13B C12B 118.7(3) . . ?
C14B C13B H13B 120.6 . . ?
C12B C13B H13B 120.6 . . ?
F14B C14B C15B 119.1(3) . . ?
F14B C14B C13B 118.6(3) . . ?
C15B C14B C13B 122.4(3) . . ?
C14B C15B C16B 119.3(3) . . ?
C14B C15B H15B 120.4 . . ?
C16B C15B H15B 120.4 . . ?
C11B C16B C15B 118.9(3) . . ?
C11B C16B H16B 120.6 . . ?
C15B C16B H16B 120.6 . . ?
C26B C21B C22B 118.2(3) . . ?
C26B C21B N1B 121.2(3) . . ?
C22B C21B N1B 120.6(3) . . ?
N23B C22B C21B 122.9(3) . . ?
N23B C22B H22B 118.5 . . ?
C21B C22B H22B 118.5 . . ?
C24B N23B C22B 117.8(3) . . ?
N23B C24B C25B 123.0(3) . . ?
N23B C24B H24B 118.5 . . ?
C25B C24B H24B 118.5 . . ?
C24B C25B C26B 118.8(3) . . ?
C24B C25B H25B 120.6 . . ?
C26B C25B H25B 120.6 . . ?
C21B C26B C25B 119.3(3) . . ?
C21B C26B H26B 120.4 . . ?
C25B C26B H26B 120.4 . . ?

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
C11A O2A C1A O1A -1.2(4) . . . . ?
C11A O2A C1A N1A 179.5(2) . . . . ?
O1A C1A N1A C21A 0.4(5) . . . . ?
O2A C1A N1A C21A 179.7(3) . . . . ?
C1A O2A C11A C12A -61.5(4) . . . . ?
C1A O2A C11A C16A 122.2(3) . . . . ?
C16A C11A C12A C13A -0.8(5) . . . . ?
O2A C11A C12A C13A -177.0(3) . . . . ?
C11A C12A C13A C14A 0.8(4) . . . . ?
C12A C13A C14A F14A 179.7(3) . . . . ?
C12A C13A C14A C15A -0.1(5) . . . . ?
F14A C14A C15A C16A 179.5(3) . . . . ?
C13A C14A C15A C16A -0.6(5) . . . . ?
C12A C11A C16A C15A 0.1(5) . . . . ?
O2A C11A C16A C15A 176.4(3) . . . . ?
C14A C15A C16A C11A 0.6(5) . . . . ?
C1A N1A C21A C26A -168.0(3) . . . . ?
C1A N1A C21A C22A 13.8(5) . . . . ?
C26A C21A C22A N23A 0.6(5) . . . . ?
N1A C21A C22A N23A 178.9(3) . . . . ?
C21A C22A N23A C24A -0.9(5) . . . . ?
C22A N23A C24A C25A 1.0(5) . . . . ?
N23A C24A C25A C26A -0.8(6) . . . . ?
C24A C25A C26A C21A 0.4(5) . . . . ?
C22A C21A C26A C25A -0.3(4) . . . . ?
N1A C21A C26A C25A -178.7(3) . . . . ?
C11B O2B C1B O1B 2.6(5) . . . . ?
C11B O2B C1B N1B -179.0(3) . . . . ?
O1B C1B N1B C21B -4.6(5) . . . . ?
O2B C1B N1B C21B 177.0(3) . . . . ?
C1B O2B C11B C12B 54.1(4) . . . . ?
C1B O2B C11B C16B -129.9(3) . . . . ?
C16B C11B C12B C13B 1.2(5) . . . . ?
O2B C11B C12B C13B 177.1(3) . . . . ?
C11B C12B C13B C14B -0.6(5) . . . . ?
C12B C13B C14B F14B 179.6(3) . . . . ?
C12B C13B C14B C15B -0.5(6) . . . . ?
F14B C14B C15B C16B -179.1(3) . . . . ?
C13B C14B C15B C16B 1.0(6) . . . . ?
C12B C11B C16B C15B -0.7(5) . . . . ?
O2B C11B C16B C15B -176.8(3) . . . . ?
C14B C15B C16B C11B -0.4(5) . . . . ?
C1B N1B C21B C26B 137.8(3) . . . . ?
C1B N1B C21B C22B -43.7(5) . . . . ?
C26B C21B C22B N23B -0.6(5) . . . . ?
N1B C21B C22B N23B -179.2(3) . . . . ?
C21B C22B N23B C24B 0.1(5) . . . . ?
C22B N23B C24B C25B 0.4(5) . . . . ?
N23B C24B C25B C26B -0.4(5) . . . . ?
C22B C21B C26B C25B 0.6(5) . . . . ?
N1B C21B C26B C25B 179.2(3) . . . . ?
C24B C25B C26B C21B -0.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
N1A H1A N23B 0.80(3) 2.20(3) 2.999(4) 174(3) . yes
N1B H1B N23A 0.79(4) 2.16(4) 2.941(4) 179(4) 2_564 yes
C16A H16A O1B 0.93 2.30 3.201(4) 164 1_545 yes
C16B H16B O1A 0.93 2.43 3.313(4) 160 2_574 yes
C22A H22A O1A 0.93 2.26 2.867(4) 122 . yes
C22B H22B O1B 0.93 2.55 2.933(4) 105 . yes
#   C22B H22B O2A   0.93      2.63      3.332(4)  132       .      yes


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone:chloroform'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_CmmCl_[11-072-Ia]
_database_code_depnum_ccdc_archive 'CCDC 1829152'
loop_
_audit_author_name
_audit_author_address
'John Gallagher'
;Dublin City University
Republic of Ireland
;
_audit_update_record             
;
2018-03-12 deposited with the CCDC.	2019-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        3-Chlorophenyl-N-3-pyridylcarbamate
_chemical_name_common            CmmCl
_chemical_melting_point          443
_chemical_formula_moiety         'C12 H9 Cl N2 O2'
_chemical_formula_sum            'C12 H9 Cl N2 O2'
_chemical_formula_weight         248.66

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I a'
_space_group_name_Hall           'I -2ya'

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

_cell_length_a                   12.0058(9)
_cell_length_b                   3.7726(6)
_cell_length_c                   24.477(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.046(11)
_cell_angle_gamma                90
_cell_volume                     1107.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    635
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      24.54

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.335
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Empirical SCALE3 ABSPACK)'
_exptl_absorpt_correction_T_min  0.37
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         7869
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_diffrn_detector_area_resol_mean 16.056
_diffrn_reflns_number            3732
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.334
_diffrn_reflns_theta_max         27.792
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.791
_diffrn_reflns_point_group_measured_fraction_full 0.865
_reflns_number_total             2059
_reflns_number_gt                1100
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_max     0.640
_reflns_Friedel_fraction_full    0.731

_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7
_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)+(0.1056P)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_abs_structure_details 
;
 Flack x determined using 311 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2059
_refine_ls_number_parameters     154
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1426
_refine_ls_R_factor_gt           0.0808
_refine_ls_wR_factor_ref         0.2330
_refine_ls_wR_factor_gt          0.1828
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.085

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
Cl13 Cl 1.0091(3) 0.9972(10) 1.00047(17) 0.0910(10) Uani 1 1 d . . . . .
O1 O 0.9259(6) 1.322(2) 0.8015(3) 0.083(2) Uani 1 1 d . . . . .
C1 C 0.9951(8) 1.176(3) 0.7763(4) 0.069(3) Uani 1 1 d . . . . .
N1 N 0.9898(6) 1.085(2) 0.7243(4) 0.067(2) Uani 1 1 d . . . . .
H1 H 1.0479 0.9889 0.7113 0.100 Uiso 1 1 calc R U . . .
O2 O 1.0993(5) 1.081(2) 0.7995(3) 0.072(2) Uani 1 1 d . . . . .
C11 C 1.1244(8) 1.161(3) 0.8540(5) 0.064(3) Uani 1 1 d . . . . .
C12 C 1.0578(9) 1.060(3) 0.8949(4) 0.061(2) Uani 1 1 d . . . . .
H12 H 0.9898 0.9494 0.8864 0.073 Uiso 1 1 calc R U . . .
C13 C 1.0914(8) 1.120(3) 0.9477(5) 0.068(3) Uani 1 1 d . . . . .
C14 C 1.1957(8) 1.286(3) 0.9610(5) 0.074(3) Uani 1 1 d . . . . .
H14 H 1.2193 1.3307 0.9971 0.089 Uiso 1 1 calc R U . . .
C15 C 1.2594(9) 1.376(3) 0.9192(6) 0.079(3) Uani 1 1 d . . . . .
H15 H 1.3282 1.4820 0.9274 0.094 Uiso 1 1 calc R U . . .
C16 C 1.2283(8) 1.320(3) 0.8664(5) 0.070(3) Uani 1 1 d . . . . .
H16 H 1.2744 1.3847 0.8388 0.084 Uiso 1 1 calc R U . . .
C21 C 0.8954(7) 1.134(3) 0.6884(4) 0.063(3) Uani 1 1 d . . . . .
C22 C 0.7879(7) 1.095(3) 0.7064(5) 0.073(3) Uani 1 1 d . . . . .
H22 H 0.7795 1.0410 0.7430 0.088 Uiso 1 1 calc R U . . .
N23 N 0.6962(6) 1.131(3) 0.6733(4) 0.079(3) Uani 1 1 d . . . . .
C24 C 0.7091(8) 1.208(3) 0.6220(5) 0.080(3) Uani 1 1 d . . . . .
H24 H 0.6460 1.2358 0.5987 0.096 Uiso 1 1 calc R U . . .
C25 C 0.8133(9) 1.251(4) 0.6008(5) 0.085(4) Uani 1 1 d . . . . .
H25 H 0.8200 1.3040 0.5641 0.102 Uiso 1 1 calc R U . . .
C26 C 0.9061(8) 1.212(3) 0.6355(5) 0.074(3) Uani 1 1 d . . . . .
H26 H 0.9768 1.2392 0.6222 0.088 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
Cl13 C13 1.730(11) . ?
O1 C1 1.195(12) . ?
C1 N1 1.318(13) . ?
C1 O2 1.392(11) . ?
N1 C21 1.408(12) . ?
N1 H1 0.8600 . ?
O2 C11 1.385(13) . ?
C11 C12 1.368(15) . ?
C11 C16 1.402(13) . ?
C12 C13 1.354(15) . ?
C12 H12 0.9300 . ?
C13 C14 1.422(15) . ?
C14 C15 1.352(15) . ?
C14 H14 0.9300 . ?
C15 C16 1.342(15) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C26 1.342(14) . ?
C21 C22 1.394(13) . ?
C22 N23 1.338(13) . ?
C22 H22 0.9300 . ?
N23 C24 1.307(14) . ?
C24 C25 1.388(15) . ?
C24 H24 0.9300 . ?
C25 C26 1.372(14) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 128.3(9) . . ?
O1 C1 O2 122.8(10) . . ?
N1 C1 O2 108.9(8) . . ?
C1 N1 C21 124.3(8) . . ?
C1 N1 H1 117.9 . . ?
C21 N1 H1 117.9 . . ?
C11 O2 C1 118.8(8) . . ?
C12 C11 O2 122.5(9) . . ?
C12 C11 C16 120.6(10) . . ?
O2 C11 C16 116.6(9) . . ?
C13 C12 C11 119.7(10) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.4(10) . . ?
C12 C13 Cl13 121.0(9) . . ?
C14 C13 Cl13 118.6(9) . . ?
C15 C14 C13 117.7(10) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C16 C15 C14 123.3(10) . . ?
C16 C15 H15 118.4 . . ?
C14 C15 H15 118.4 . . ?
C15 C16 C11 118.4(10) . . ?
C15 C16 H16 120.8 . . ?
C11 C16 H16 120.8 . . ?
C26 C21 C22 117.7(9) . . ?
C26 C21 N1 121.0(8) . . ?
C22 C21 N1 121.2(9) . . ?
N23 C22 C21 123.0(10) . . ?
N23 C22 H22 118.5 . . ?
C21 C22 H22 118.5 . . ?
C24 N23 C22 118.0(8) . . ?
N23 C24 C25 122.7(10) . . ?
N23 C24 H24 118.7 . . ?
C25 C24 H24 118.7 . . ?
C26 C25 C24 118.4(10) . . ?
C26 C25 H25 120.8 . . ?
C24 C25 H25 120.8 . . ?
C21 C26 C25 120.3(9) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?

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
O1 C1 N1 C21 -3(2) . . . . ?
O2 C1 N1 C21 178.6(9) . . . . ?
O1 C1 O2 C11 -0.3(17) . . . . ?
N1 C1 O2 C11 178.3(9) . . . . ?
C1 O2 C11 C12 53.8(15) . . . . ?
C1 O2 C11 C16 -132.9(10) . . . . ?
O2 C11 C12 C13 174.6(10) . . . . ?
C16 C11 C12 C13 1.5(15) . . . . ?
C11 C12 C13 C14 -0.5(15) . . . . ?
C11 C12 C13 Cl13 179.7(8) . . . . ?
C12 C13 C14 C15 -0.6(16) . . . . ?
Cl13 C13 C14 C15 179.2(9) . . . . ?
C13 C14 C15 C16 0.7(18) . . . . ?
C14 C15 C16 C11 0.2(17) . . . . ?
C12 C11 C16 C15 -1.4(15) . . . . ?
O2 C11 C16 C15 -174.9(10) . . . . ?
C1 N1 C21 C26 145.6(11) . . . . ?
C1 N1 C21 C22 -36.0(18) . . . . ?
C26 C21 C22 N23 0(2) . . . . ?
N1 C21 C22 N23 -178.4(11) . . . . ?
C21 C22 N23 C24 0(2) . . . . ?
C22 N23 C24 C25 0(2) . . . . ?
N23 C24 C25 C26 0(2) . . . . ?
C22 C21 C26 C25 0.0(19) . . . . ?
N1 C21 C26 C25 178.5(12) . . . . ?
C24 C25 C26 C21 0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A    D...A      D-H...A   symm   publ
#   -    -    -     ---       -----    -----      -------   ----   ----
N1 H1 N23 0.86 2.10 2.948(11) 167 2_575 yes
C16 H16 O1 0.93 2.35 3.223(12) 155 2_585 yes
C22 H22 O1 0.93 2.45 2.913(14) 111 . yes
#   C25  H25  Cl13  0.93      2.92     3.617(12)  133       4_474  yes



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform:acetone:toluene'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_CmpBr_[11-006]
_database_code_depnum_ccdc_archive 'CCDC 1829150'
loop_
_audit_author_name
_audit_author_address
'John Gallagher'
;Dublin City University
Republic of Ireland
;
_audit_update_record             
;
2018-03-12 deposited with the CCDC.	2019-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4-Bromobenzene-N-3-pyridylcarbamate
_chemical_name_common            CmpBr
_chemical_melting_point          442
_chemical_formula_moiety         'C12 H9 Br N2 O2'
_chemical_formula_sum            'C12 H9 Br N2 O2'
_chemical_formula_weight         293.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.2502(3)
_cell_length_b                   3.8621(1)
_cell_length_c                   22.9979(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.861(2)
_cell_angle_gamma                90
_cell_volume                     1172.65(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1620
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.09

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.496
_shelx_estimated_absorpt_T_min   0.622
_shelx_estimated_absorpt_T_max   0.845
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'
_exptl_absorpt_correction_T_min  0.577
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         7674
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_diffrn_detector_area_resol_mean 16.056
_diffrn_reflns_number            7123
_diffrn_reflns_av_unetI/netI     0.0688
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.253
_diffrn_reflns_theta_max         27.145
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.702
_diffrn_reflns_point_group_measured_fraction_full 0.734
_reflns_number_total             3624
_reflns_number_gt                2408
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.450
_reflns_Friedel_fraction_max     0.436
_reflns_Friedel_fraction_full    0.469

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7

_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)+(0.0205P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
Classical Flack method
;
_refine_ls_abs_structure_Flack   0.019(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3624
_refine_ls_number_parameters     315
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0776
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.056

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
Br1A Br 0.46026(6) 0.6274(3) 0.10172(5) 0.0890(4) Uani 1 1 d . . . . .
O1A O 0.0305(4) 0.4265(14) 0.2248(2) 0.0476(13) Uani 1 1 d . . . . .
O2A O 0.0181(3) 0.7335(13) 0.1407(2) 0.0501(13) Uani 1 1 d . . . . .
C1A C -0.0199(5) 0.5864(18) 0.1884(3) 0.0362(16) Uani 1 1 d . . . . .
N1A N -0.1196(4) 0.6524(17) 0.1865(3) 0.0422(15) Uani 1 1 d . . . . .
H1A H -0.141(6) 0.78(2) 0.158(4) 0.06(3) Uiso 1 1 d . . . . .
C11A C 0.1217(5) 0.694(2) 0.1348(3) 0.0384(17) Uani 1 1 d . . . . .
C12A C 0.1925(5) 0.838(2) 0.1746(3) 0.0433(18) Uani 1 1 d . . . . .
H12A H 0.1725 0.9484 0.2077 0.052 Uiso 1 1 calc R U . . .
C13A C 0.2940(6) 0.8163(19) 0.1650(4) 0.050(2) Uani 1 1 d . . . . .
H13A H 0.3431 0.9117 0.1916 0.060 Uiso 1 1 calc R U . . .
C14A C 0.3211(5) 0.6540(18) 0.1163(4) 0.0477(19) Uani 1 1 d . . . . .
C15A C 0.2511(6) 0.5153(19) 0.0754(4) 0.050(2) Uani 1 1 d . . . . .
H15A H 0.2713 0.4095 0.0420 0.060 Uiso 1 1 calc R U . . .
C16A C 0.1492(6) 0.5369(19) 0.0852(3) 0.0468(19) Uani 1 1 d . . . . .
H16A H 0.1000 0.4454 0.0583 0.056 Uiso 1 1 calc R U . . .
C21A C -0.1849(5) 0.5431(17) 0.2276(3) 0.0345(16) Uani 1 1 d . . . . .
C22A C -0.1549(5) 0.4150(19) 0.2818(3) 0.0446(19) Uani 1 1 d . . . . .
H22A H -0.0857 0.3941 0.2919 0.053 Uiso 1 1 calc R U . . .
N23A N -0.2169(5) 0.3188(17) 0.3210(3) 0.0497(17) Uani 1 1 d . . . . .
C24A C -0.3160(6) 0.348(2) 0.3057(4) 0.049(2) Uani 1 1 d . . . . .
H24A H -0.3612 0.2822 0.3324 0.059 Uiso 1 1 calc R U . . .
C25A C -0.3541(6) 0.471(2) 0.2525(4) 0.056(2) Uani 1 1 d . . . . .
H25A H -0.4237 0.4893 0.2434 0.067 Uiso 1 1 calc R U . . .
C26A C -0.2881(5) 0.5670(19) 0.2130(3) 0.0461(18) Uani 1 1 d . . . . .
H26A H -0.3124 0.6479 0.1764 0.055 Uiso 1 1 calc R U . . .
Br1B Br 0.46140(7) 1.2289(3) -0.13400(5) 0.0857(4) Uani 1 1 d . . . . .
O1B O 0.0196(4) 1.1857(16) -0.0228(3) 0.0614(16) Uani 1 1 d . . . . .
O2B O 0.0200(4) 0.9376(14) -0.1120(2) 0.0528(14) Uani 1 1 d . . . . .
C1B C -0.0248(6) 1.039(2) -0.0638(3) 0.0450(18) Uani 1 1 d . . . . .
N1B N -0.1233(4) 0.9503(17) -0.0683(3) 0.0442(15) Uani 1 1 d . . . . .
H1B H -0.145(5) 0.860(16) -0.103(3) 0.030(18) Uiso 1 1 d . . . . .
C11B C 0.1232(6) 1.013(2) -0.1137(3) 0.0422(19) Uani 1 1 d . . . . .
C12B C 0.1947(6) 0.900(2) -0.0709(3) 0.049(2) Uani 1 1 d . . . . .
H12B H 0.1757 0.7820 -0.0383 0.058 Uiso 1 1 calc R U . . .
C13B C 0.2959(6) 0.968(2) -0.0777(4) 0.054(2) Uani 1 1 d . . . . .
H13B H 0.3458 0.8986 -0.0492 0.065 Uiso 1 1 calc R U . . .
C14B C 0.3216(6) 1.136(2) -0.1258(4) 0.051(2) Uani 1 1 d . . . . .
C15B C 0.2522(6) 1.2410(19) -0.1688(4) 0.051(2) Uani 1 1 d . . . . .
H15B H 0.2722 1.3535 -0.2017 0.061 Uiso 1 1 calc R U . . .
C16B C 0.1507(6) 1.1778(19) -0.1627(4) 0.052(2) Uani 1 1 d . . . . .
H16B H 0.1016 1.2466 -0.1917 0.062 Uiso 1 1 calc R U . . .
C21B C -0.1870(5) 1.0035(17) -0.0243(3) 0.0374(17) Uani 1 1 d . . . . .
C22B C -0.1561(5) 0.932(2) 0.0341(3) 0.0463(19) Uani 1 1 d . . . . .
H22B H -0.0908 0.8488 0.0430 0.056 Uiso 1 1 calc R U . . .
N23B N -0.2147(5) 0.9774(17) 0.0775(3) 0.0450(16) Uani 1 1 d . . . . .
C24B C -0.3080(6) 1.090(2) 0.0638(4) 0.050(2) Uani 1 1 d . . . . .
H24B H -0.3498 1.1271 0.0937 0.061 Uiso 1 1 calc R U . . .
C25B C -0.3459(6) 1.155(2) 0.0074(4) 0.059(2) Uani 1 1 d . . . . .
H25B H -0.4127 1.2257 -0.0006 0.070 Uiso 1 1 calc R U . . .
C26B C -0.2839(5) 1.1158(19) -0.0371(3) 0.0457(18) Uani 1 1 d . . . . .
H26B H -0.3076 1.1650 -0.0754 0.055 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
Br1A C14A 1.905(7) . ?
O1A C1A 1.197(8) . ?
O2A C1A 1.370(8) . ?
O2A C11A 1.399(8) . ?
C1A N1A 1.341(9) . ?
N1A C21A 1.400(9) . ?
N1A H1A 0.84(8) . ?
C11A C16A 1.367(10) . ?
C11A C12A 1.373(10) . ?
C12A C13A 1.384(10) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.359(11) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.372(11) . ?
C15A C16A 1.390(10) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C21A C22A 1.369(10) . ?
C21A C26A 1.383(9) . ?
C22A N23A 1.323(10) . ?
C22A H22A 0.9300 . ?
N23A C24A 1.335(10) . ?
C24A C25A 1.368(11) . ?
C24A H24A 0.9300 . ?
C25A C26A 1.365(11) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
Br1B C14B 1.911(7) . ?
O1B C1B 1.210(8) . ?
O2B C1B 1.358(9) . ?
O2B C11B 1.401(8) . ?
C1B N1B 1.344(9) . ?
N1B C21B 1.389(9) . ?
N1B H1B 0.89(7) . ?
C11B C16B 1.370(11) . ?
C11B C12B 1.379(10) . ?
C12B C13B 1.387(10) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.351(12) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.354(11) . ?
C15B C16B 1.385(10) . ?
C15B H15B 0.9300 . ?
C16B H16B 0.9300 . ?
C21B C26B 1.363(9) . ?
C21B C22B 1.397(10) . ?
C22B N23B 1.327(10) . ?
C22B H22B 0.9300 . ?
N23B C24B 1.324(9) . ?
C24B C25B 1.374(11) . ?
C24B H24B 0.9300 . ?
C25B C26B 1.375(11) . ?
C25B H25B 0.9300 . ?
C26B H26B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A O2A C11A 117.6(5) . . ?
O1A C1A N1A 127.7(7) . . ?
O1A C1A O2A 123.5(6) . . ?
N1A C1A O2A 108.8(6) . . ?
C1A N1A C21A 125.7(7) . . ?
C1A N1A H1A 114(5) . . ?
C21A N1A H1A 121(5) . . ?
C16A C11A C12A 121.4(7) . . ?
C16A C11A O2A 117.5(6) . . ?
C12A C11A O2A 120.7(7) . . ?
C11A C12A C13A 119.2(7) . . ?
C11A C12A H12A 120.4 . . ?
C13A C12A H12A 120.4 . . ?
C14A C13A C12A 119.2(7) . . ?
C14A C13A H13A 120.4 . . ?
C12A C13A H13A 120.4 . . ?
C13A C14A C15A 122.3(7) . . ?
C13A C14A Br1A 119.8(6) . . ?
C15A C14A Br1A 117.9(6) . . ?
C14A C15A C16A 118.4(7) . . ?
C14A C15A H15A 120.8 . . ?
C16A C15A H15A 120.8 . . ?
C11A C16A C15A 119.5(7) . . ?
C11A C16A H16A 120.2 . . ?
C15A C16A H16A 120.2 . . ?
C22A C21A C26A 116.8(7) . . ?
C22A C21A N1A 125.1(6) . . ?
C26A C21A N1A 118.1(6) . . ?
N23A C22A C21A 124.9(7) . . ?
N23A C22A H22A 117.6 . . ?
C21A C22A H22A 117.6 . . ?
C22A N23A C24A 116.8(7) . . ?
N23A C24A C25A 123.0(7) . . ?
N23A C24A H24A 118.5 . . ?
C25A C24A H24A 118.5 . . ?
C26A C25A C24A 118.7(8) . . ?
C26A C25A H25A 120.6 . . ?
C24A C25A H25A 120.6 . . ?
C25A C26A C21A 119.8(7) . . ?
C25A C26A H26A 120.1 . . ?
C21A C26A H26A 120.1 . . ?
C1B O2B C11B 117.3(6) . . ?
O1B C1B N1B 125.8(7) . . ?
O1B C1B O2B 123.5(7) . . ?
N1B C1B O2B 110.7(7) . . ?
C1B N1B C21B 123.5(7) . . ?
C1B N1B H1B 114(4) . . ?
C21B N1B H1B 122(4) . . ?
C16B C11B C12B 121.3(7) . . ?
C16B C11B O2B 116.6(7) . . ?
C12B C11B O2B 121.8(7) . . ?
C11B C12B C13B 118.2(7) . . ?
C11B C12B H12B 120.9 . . ?
C13B C12B H12B 120.9 . . ?
C14B C13B C12B 119.8(8) . . ?
C14B C13B H13B 120.1 . . ?
C12B C13B H13B 120.1 . . ?
C13B C14B C15B 122.6(7) . . ?
C13B C14B Br1B 119.0(7) . . ?
C15B C14B Br1B 118.4(6) . . ?
C14B C15B C16B 118.6(7) . . ?
C14B C15B H15B 120.7 . . ?
C16B C15B H15B 120.7 . . ?
C11B C16B C15B 119.6(7) . . ?
C11B C16B H16B 120.2 . . ?
C15B C16B H16B 120.2 . . ?
C26B C21B N1B 120.6(7) . . ?
C26B C21B C22B 117.7(7) . . ?
N1B C21B C22B 121.7(6) . . ?
N23B C22B C21B 123.7(7) . . ?
N23B C22B H22B 118.2 . . ?
C21B C22B H22B 118.2 . . ?
C24B N23B C22B 117.3(6) . . ?
N23B C24B C25B 122.9(7) . . ?
N23B C24B H24B 118.5 . . ?
C25B C24B H24B 118.5 . . ?
C24B C25B C26B 119.3(7) . . ?
C24B C25B H25B 120.3 . . ?
C26B C25B H25B 120.3 . . ?
C21B C26B C25B 119.0(7) . . ?
C21B C26B H26B 120.5 . . ?
C25B C26B H26B 120.5 . . ?

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
C11A O2A C1A O1A -0.2(10) . . . . ?
C11A O2A C1A N1A 179.9(6) . . . . ?
O1A C1A N1A C21A -0.1(12) . . . . ?
O2A C1A N1A C21A 179.7(6) . . . . ?
C1A O2A C11A C16A 121.7(7) . . . . ?
C1A O2A C11A C12A -64.6(9) . . . . ?
C16A C11A C12A C13A -1.6(12) . . . . ?
O2A C11A C12A C13A -175.0(6) . . . . ?
C11A C12A C13A C14A 0.2(11) . . . . ?
C12A C13A C14A C15A 1.2(11) . . . . ?
C12A C13A C14A Br1A 179.1(5) . . . . ?
C13A C14A C15A C16A -1.3(11) . . . . ?
Br1A C14A C15A C16A -179.2(5) . . . . ?
C12A C11A C16A C15A 1.5(12) . . . . ?
O2A C11A C16A C15A 175.1(6) . . . . ?
C14A C15A C16A C11A -0.1(11) . . . . ?
C1A N1A C21A C22A 14.2(11) . . . . ?
C1A N1A C21A C26A -166.2(7) . . . . ?
C26A C21A C22A N23A -1.1(11) . . . . ?
N1A C21A C22A N23A 178.5(7) . . . . ?
C21A C22A N23A C24A 0.4(12) . . . . ?
C22A N23A C24A C25A 0.0(12) . . . . ?
N23A C24A C25A C26A 0.3(13) . . . . ?
C24A C25A C26A C21A -1.0(12) . . . . ?
C22A C21A C26A C25A 1.3(11) . . . . ?
N1A C21A C26A C25A -178.3(7) . . . . ?
C11B O2B C1B O1B -0.6(11) . . . . ?
C11B O2B C1B N1B 179.8(6) . . . . ?
O1B C1B N1B C21B -3.2(12) . . . . ?
O2B C1B N1B C21B 176.3(6) . . . . ?
C1B O2B C11B C16B -128.8(7) . . . . ?
C1B O2B C11B C12B 56.9(10) . . . . ?
C16B C11B C12B C13B 2.1(12) . . . . ?
O2B C11B C12B C13B 176.1(7) . . . . ?
C11B C12B C13B C14B -1.1(12) . . . . ?
C12B C13B C14B C15B -0.3(13) . . . . ?
C12B C13B C14B Br1B 179.6(6) . . . . ?
C13B C14B C15B C16B 0.7(12) . . . . ?
Br1B C14B C15B C16B -179.2(5) . . . . ?
C12B C11B C16B C15B -1.7(12) . . . . ?
O2B C11B C16B C15B -176.1(6) . . . . ?
C14B C15B C16B C11B 0.3(11) . . . . ?
C1B N1B C21B C26B 139.4(7) . . . . ?
C1B N1B C21B C22B -43.0(10) . . . . ?
C26B C21B C22B N23B -1.9(11) . . . . ?
N1B C21B C22B N23B -179.6(7) . . . . ?
C21B C22B N23B C24B 1.2(12) . . . . ?
C22B N23B C24B C25B 1.1(12) . . . . ?
N23B C24B C25B C26B -2.6(13) . . . . ?
N1B C21B C26B C25B 178.0(7) . . . . ?
C22B C21B C26B C25B 0.3(10) . . . . ?
C24B C25B C26B C21B 1.8(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
N1A H1A N23B 0.84(8) 2.17(9) 2.985(9) 164(8) . yes
N1B H1B N23A 0.89(7) 2.04(7) 2.927(9) 171(6) 2_564 yes
C16A H16A O1B 0.93 2.30 3.199(9) 163 1_545 yes
C16B H16B O1A 0.93 2.42 3.296(10) 157 2_574 yes
C22A H22A O1A 0.93 2.27 2.881(9) 122 . yes
C22B H22B O1B 0.93 2.55 2.934(9) 105 . yes
C22B H22B O2A 0.93 2.60 3.312(8) 133 . yes



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_CmmF_[10-114]
_database_code_depnum_ccdc_archive 'CCDC 1829151'
loop_
_audit_author_name
_audit_author_address
'John Gallagher'
;Dublin City University
Republic of Ireland
;
_audit_update_record             
;
2018-03-12 deposited with the CCDC.	2019-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        3-Fluorophenyl-N-3-pyridylcarbamate
_chemical_name_common            CmmF
_chemical_melting_point          425
_chemical_formula_moiety         'C12 H9 F N2 O2'
_chemical_formula_sum            'C12 H9 F N2 O2'
_chemical_formula_weight         232.21

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   26.1331(19)
_cell_length_b                   3.7572(3)
_cell_length_c                   11.9066(7)
_cell_angle_alpha                90
_cell_angle_beta                 115.765(8)
_cell_angle_gamma                90
_cell_volume                     1052.85(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1279
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.08

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         3432
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_diffrn_detector_area_resol_mean 16.056
_diffrn_reflns_number            3146
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.423
_diffrn_reflns_theta_max         27.138
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.724
_diffrn_reflns_point_group_measured_fraction_full 0.758
_reflns_number_total             1683
_reflns_number_gt                1344
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.503
_reflns_Friedel_fraction_max     0.485
_reflns_Friedel_fraction_full    0.516

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7

_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)+(0.0632P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x from 357 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack & Wagner, 2013).
;
_refine_ls_abs_structure_Flack   -4.7(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1683
_refine_ls_number_parameters     158
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.055

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
F13 F 0.28715(13) -0.0021(12) 0.7180(3) 0.0900(12) Uani 1 1 d . . . . .
O1 O 0.09360(13) 0.3296(10) 0.6069(3) 0.0655(10) Uani 1 1 d . . . . .
C1 C 0.06798(17) 0.1768(12) 0.5097(3) 0.0469(10) Uani 1 1 d . . . . .
O2 O 0.09198(12) 0.0751(10) 0.4331(2) 0.0558(9) Uani 1 1 d . . . . .
N1 N 0.01341(15) 0.0825(11) 0.4581(3) 0.0516(10) Uani 1 1 d . . . . .
H1 H -0.002(2) -0.007(15) 0.385(6) 0.076(17) Uiso 1 1 d . . . . .
C11 C 0.14852(17) 0.1470(11) 0.4680(3) 0.0437(9) Uani 1 1 d . . . . .
C12 C 0.1904(2) 0.0412(12) 0.5826(4) 0.0504(10) Uani 1 1 d . . . . .
H12 H 0.1812 -0.0680 0.6416 0.060 Uiso 1 1 calc R U . . .
C13 C 0.24509(19) 0.1026(14) 0.6057(4) 0.0563(11) Uani 1 1 d . . . . .
C14 C 0.2610(2) 0.2610(15) 0.5217(5) 0.0612(12) Uani 1 1 d . . . . .
H14 H 0.2991 0.2998 0.5412 0.073 Uiso 1 1 calc R U . . .
C15 C 0.2188(2) 0.3602(14) 0.4081(4) 0.0598(12) Uani 1 1 d . . . . .
H15 H 0.2285 0.4666 0.3495 0.072 Uiso 1 1 calc R U . . .
C16 C 0.1624(2) 0.3047(13) 0.3796(4) 0.0534(11) Uani 1 1 d . . . . .
H16 H 0.1342 0.3717 0.3023 0.064 Uiso 1 1 calc R U . . .
C21 C -0.02360(17) 0.1423(11) 0.5130(3) 0.0455(10) Uani 1 1 d . . . . .
C22 C -0.00581(19) 0.1118(13) 0.6417(3) 0.0532(11) Uani 1 1 d . . . . .
H22 H 0.0320 0.0546 0.6915 0.064 Uiso 1 1 calc R U . . .
N23 N -0.03991(15) 0.1599(11) 0.6964(3) 0.0567(10) Uani 1 1 d . . . . .
C24 C -0.0937(2) 0.2439(13) 0.6244(4) 0.0552(11) Uani 1 1 d . . . . .
H24 H -0.1179 0.2846 0.6619 0.066 Uiso 1 1 calc R U . . .
C25 C -0.11540(19) 0.2733(15) 0.4968(4) 0.0580(12) Uani 1 1 d . . . . .
H25 H -0.1536 0.3257 0.4490 0.070 Uiso 1 1 calc R U . . .
C26 C -0.07964(19) 0.2239(14) 0.4414(3) 0.0535(11) Uani 1 1 d . . . . .
H26 H -0.0933 0.2458 0.3554 0.064 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
F13 C13 1.369(6) . ?
O1 C1 1.202(5) . ?
C1 N1 1.332(6) . ?
C1 O2 1.367(5) . ?
O2 C11 1.377(5) . ?
N1 C21 1.401(5) . ?
N1 H1 0.86(7) . ?
C11 C12 1.385(6) . ?
C11 C16 1.387(6) . ?
C12 C13 1.354(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(7) . ?
C14 C15 1.374(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 C26 1.371(6) . ?
C21 C22 1.399(5) . ?
C22 N23 1.326(6) . ?
C22 H22 0.9300 . ?
N23 C24 1.328(6) . ?
C24 C25 1.377(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.371(6) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 127.4(4) . . ?
O1 C1 O2 123.4(4) . . ?
N1 C1 O2 109.1(3) . . ?
C1 O2 C11 119.2(3) . . ?
C1 N1 C21 124.0(3) . . ?
C1 N1 H1 120(4) . . ?
C21 N1 H1 116(4) . . ?
O2 C11 C12 121.7(4) . . ?
O2 C11 C16 117.1(3) . . ?
C12 C11 C16 121.0(4) . . ?
C13 C12 C11 117.6(4) . . ?
C13 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?
C12 C13 F13 118.6(4) . . ?
C12 C13 C14 123.6(4) . . ?
F13 C13 C14 117.8(4) . . ?
C13 C14 C15 117.8(4) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
C14 C15 C16 121.1(4) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C11 118.9(4) . . ?
C15 C16 H16 120.6 . . ?
C11 C16 H16 120.6 . . ?
C26 C21 C22 117.2(4) . . ?
C26 C21 N1 120.8(3) . . ?
C22 C21 N1 122.0(4) . . ?
N23 C22 C21 123.6(4) . . ?
N23 C22 H22 118.2 . . ?
C21 C22 H22 118.2 . . ?
C22 N23 C24 117.7(3) . . ?
N23 C24 C25 122.9(4) . . ?
N23 C24 H24 118.6 . . ?
C25 C24 H24 118.6 . . ?
C26 C25 C24 118.8(4) . . ?
C26 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C25 C26 C21 119.9(3) . . ?
C25 C26 H26 120.1 . . ?
C21 C26 H26 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 O2 C11 0.5(6) . . . . ?
N1 C1 O2 C11 179.8(4) . . . . ?
O1 C1 N1 C21 -1.7(8) . . . . ?
O2 C1 N1 C21 179.0(4) . . . . ?
C1 O2 C11 C12 53.8(6) . . . . ?
C1 O2 C11 C16 -131.3(4) . . . . ?
O2 C11 C12 C13 175.7(4) . . . . ?
C16 C11 C12 C13 1.1(6) . . . . ?
C11 C12 C13 F13 -179.5(4) . . . . ?
C11 C12 C13 C14 -0.4(7) . . . . ?
C12 C13 C14 C15 -0.3(8) . . . . ?
F13 C13 C14 C15 178.8(5) . . . . ?
C13 C14 C15 C16 0.4(7) . . . . ?
C14 C15 C16 C11 0.3(7) . . . . ?
O2 C11 C16 C15 -175.9(4) . . . . ?
C12 C11 C16 C15 -1.0(6) . . . . ?
C1 N1 C21 C26 144.6(5) . . . . ?
C1 N1 C21 C22 -37.3(7) . . . . ?
C26 C21 C22 N23 -0.5(7) . . . . ?
N1 C21 C22 N23 -178.7(5) . . . . ?
C21 C22 N23 C24 -0.4(7) . . . . ?
C22 N23 C24 C25 1.7(8) . . . . ?
N23 C24 C25 C26 -1.9(8) . . . . ?
C24 C25 C26 C21 0.8(8) . . . . ?
C22 C21 C26 C25 0.3(7) . . . . ?
N1 C21 C26 C25 178.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
#   C25  H25 F13    0.93      2.59      3.300(5)  134       4_454  yes
N1 H1 N23 0.86(7) 2.10(7) 2.950(5) 173(5) 2_554 yes
C16 H16 O1 0.93 2.38 3.254(5) 157 2_564 yes
C22 H22 O1 0.93 2.47 2.920(6) 110 . yes
#   C22  H22 O2     0.93      2.65      3.369(5)  134       2      yes



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_CopF_[11-014]
_database_code_depnum_ccdc_archive 'CCDC 1829154'
loop_
_audit_author_name
_audit_author_address
'John Gallagher'
;Dublin City University
Republic of Ireland
;
_audit_update_record             
;
2018-03-12 deposited with the CCDC.	2019-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4-Fluorophenyl-N-2-pyridylcarbamate
_chemical_name_common            CopF
_chemical_melting_point          452
_chemical_formula_moiety         'C12 H9 F N2 O2'
_chemical_formula_sum            'C12 H9 F N2 O2'
_chemical_formula_weight         232.21

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'
F F 0.0171 0.0103 '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                   3.8471(4)
_cell_length_b                   11.6218(19)
_cell_length_c                   12.467(2)
_cell_angle_alpha                108.261(15)
_cell_angle_beta                 90.417(11)
_cell_angle_gamma                95.461(11)
_cell_volume                     526.52(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1708
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      26.56

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.730
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.922
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         5561
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_diffrn_detector_area_resol_mean 16.056
_diffrn_reflns_number            5561
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.902
_diffrn_reflns_theta_max         26.460
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1965
_reflns_number_gt                1260
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7

_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)+(0.0436P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1965
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.036

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
F14 F 0.8934(4) 0.90083(14) 0.73785(11) 0.0882(5) Uani 1 1 d . . . . .
O1 O 0.5714(4) 0.47797(14) 0.30580(12) 0.0599(5) Uani 1 1 d . . . . .
O2 O 0.9101(4) 0.64187(14) 0.28941(11) 0.0547(4) Uani 1 1 d . . . . .
C1 C 0.7408(6) 0.5273(2) 0.24888(18) 0.0473(6) Uani 1 1 d . . . . .
N1 N 0.8002(5) 0.48185(17) 0.13762(15) 0.0468(5) Uani 1 1 d . . . . .
H1 H 0.927(6) 0.531(2) 0.1043(18) 0.066(8) Uiso 1 1 d . . . . .
C11 C 0.8974(5) 0.7034(2) 0.40541(18) 0.0452(5) Uani 1 1 d . . . . .
C12 C 1.0200(5) 0.6564(2) 0.48476(18) 0.0503(6) Uani 1 1 d . . . . .
H12 H 1.1053 0.5806 0.4627 0.060 Uiso 1 1 calc R U . . .
C13 C 1.0154(6) 0.7229(2) 0.59756(19) 0.0542(6) Uani 1 1 d . . . . .
H13 H 1.0926 0.6921 0.6530 0.065 Uiso 1 1 calc R U . . .
C14 C 0.8950(6) 0.8348(2) 0.62602(19) 0.0548(6) Uani 1 1 d . . . . .
C15 C 0.7814(6) 0.8840(2) 0.5485(2) 0.0566(6) Uani 1 1 d . . . . .
H15 H 0.7060 0.9614 0.5710 0.068 Uiso 1 1 calc R U . . .
C16 C 0.7804(6) 0.8164(2) 0.43517(19) 0.0511(6) Uani 1 1 d . . . . .
H16 H 0.7014 0.8473 0.3801 0.061 Uiso 1 1 calc R U . . .
C21 C 0.6781(5) 0.3665(2) 0.06557(17) 0.0424(5) Uani 1 1 d . . . . .
N22 N 0.7664(4) 0.34891(16) -0.04152(14) 0.0479(5) Uani 1 1 d . . . . .
C23 C 0.6662(6) 0.2398(2) -0.11611(19) 0.0568(6) Uani 1 1 d . . . . .
H23 H 0.7249 0.2268 -0.1909 0.068 Uiso 1 1 calc R U . . .
C24 C 0.4823(6) 0.1456(2) -0.08992(19) 0.0582(7) Uani 1 1 d . . . . .
H24 H 0.4205 0.0708 -0.1447 0.070 Uiso 1 1 calc R U . . .
C25 C 0.3931(6) 0.1666(2) 0.0209(2) 0.0573(6) Uani 1 1 d . . . . .
H25 H 0.2662 0.1055 0.0420 0.069 Uiso 1 1 calc R U . . .
C26 C 0.4906(5) 0.2770(2) 0.10004(19) 0.0499(6) Uani 1 1 d . . . . .
H26 H 0.4328 0.2918 0.1751 0.060 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
F14 C14 1.365(2) . ?
O1 C1 1.203(2) . ?
O2 C1 1.364(3) . ?
O2 C11 1.402(2) . ?
C1 N1 1.350(3) . ?
N1 C21 1.394(3) . ?
N1 H1 0.91(2) . ?
C11 C16 1.369(3) . ?
C11 C12 1.371(3) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.356(3) . ?
C15 C16 1.385(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 N22 1.337(2) . ?
C21 C26 1.389(3) . ?
N22 C23 1.335(3) . ?
C23 C24 1.373(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.367(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C11 117.71(16) . . ?
O1 C1 N1 127.5(2) . . ?
O1 C1 O2 124.0(2) . . ?
N1 C1 O2 108.48(19) . . ?
C1 N1 C21 126.4(2) . . ?
C1 N1 H1 118.2(14) . . ?
C21 N1 H1 115.3(14) . . ?
C16 C11 C12 121.7(2) . . ?
C16 C11 O2 116.6(2) . . ?
C12 C11 O2 121.5(2) . . ?
C11 C12 C13 119.3(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 118.4(2) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C15 C14 C13 123.1(2) . . ?
C15 C14 F14 118.6(2) . . ?
C13 C14 F14 118.3(2) . . ?
C14 C15 C16 118.5(2) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C11 C16 C15 119.0(2) . . ?
C11 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
N22 C21 C26 122.6(2) . . ?
N22 C21 N1 112.96(19) . . ?
C26 C21 N1 124.4(2) . . ?
C23 N22 C21 117.0(2) . . ?
N22 C23 C24 124.5(2) . . ?
N22 C23 H23 117.8 . . ?
C24 C23 H23 117.8 . . ?
C23 C24 C25 117.2(2) . . ?
C23 C24 H24 121.4 . . ?
C25 C24 H24 121.4 . . ?
C26 C25 C24 120.2(2) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C21 118.4(2) . . ?
C25 C26 H26 120.8 . . ?
C21 C26 H26 120.8 . . ?

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
C11 O2 C1 O1 2.8(3) . . . . ?
C11 O2 C1 N1 -176.71(18) . . . . ?
O1 C1 N1 C21 -0.7(4) . . . . ?
O2 C1 N1 C21 178.85(18) . . . . ?
C1 O2 C11 C16 -125.9(2) . . . . ?
C1 O2 C11 C12 58.8(3) . . . . ?
C16 C11 C12 C13 2.1(3) . . . . ?
O2 C11 C12 C13 177.21(18) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C12 C13 C14 F14 -179.49(18) . . . . ?
C13 C14 C15 C16 1.5(4) . . . . ?
F14 C14 C15 C16 -179.44(18) . . . . ?
C12 C11 C16 C15 -1.0(3) . . . . ?
O2 C11 C16 C15 -176.35(17) . . . . ?
C14 C15 C16 C11 -0.8(3) . . . . ?
C1 N1 C21 N22 177.3(2) . . . . ?
C1 N1 C21 C26 -4.1(3) . . . . ?
C26 C21 N22 C23 0.0(3) . . . . ?
N1 C21 N22 C23 178.69(18) . . . . ?
C21 N22 C23 C24 -0.4(3) . . . . ?
N22 C23 C24 C25 0.8(4) . . . . ?
C23 C24 C25 C26 -0.7(3) . . . . ?
C24 C25 C26 C21 0.4(3) . . . . ?
N22 C21 C26 C25 0.0(3) . . . . ?
N1 C21 C26 C25 -178.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
N1 H1 N22 0.91(2) 2.08(3) 2.994(3) 175(2) 2_765 yes
C23 H23 O2 0.93 2.57 3.271(3) 133 2_765 yes
C26 H26 O1 0.93 2.28 2.868(3) 121 . yes
#   C13  H13  O1    0.93      2.64      3.445(3)  146       2_766  yes


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform:acetone'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_CopCl_[11-016]
_database_code_depnum_ccdc_archive 'CCDC 1829155'
loop_
_audit_author_name
_audit_author_address
'John Gallagher'
;Dublin City University
Republic of Ireland
;
_audit_update_record             
;
2018-03-12 deposited with the CCDC.	2019-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4-Chlorophenyl-N-2-pyridylcarbamate
_chemical_name_common            CopCl
_chemical_melting_point          472
_chemical_formula_moiety         'C12 H9 Cl N2 O2'
_chemical_formula_sum            'C12 H9 Cl N2 O2'
_chemical_formula_weight         248.66

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

_space_group_crystal_system      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                   3.8776(9)
_cell_length_b                   11.481(4)
_cell_length_c                   13.085(5)
_cell_angle_alpha                105.84(3)
_cell_angle_beta                 90.64(2)
_cell_angle_gamma                92.82(2)
_cell_volume                     559.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    415
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      21.79

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    0.331
_shelx_estimated_absorpt_T_min   0.844
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.585
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Empirical SCALE3 ABSPACK'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         4262
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_diffrn_detector_area_resol_mean 16.056
_diffrn_reflns_number            4234
_diffrn_reflns_av_unetI/netI     0.1144
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.769
_diffrn_reflns_theta_max         25.188
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1972
_reflns_number_gt                930
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7
_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)+(0.0845P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1972
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1604
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_ref         0.2243
_refine_ls_wR_factor_gt          0.1726
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.071

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
Cl14 Cl 0.9245(5) 0.90160(19) 0.72359(13) 0.0912(8) Uani 1 1 d . . . . .
O1 O 0.6029(10) 0.4691(4) 0.2924(3) 0.0662(12) Uani 1 1 d . . . . .
O2 O 0.9246(10) 0.6326(4) 0.2739(3) 0.0651(11) Uani 1 1 d . . . . .
C1 C 0.7576(15) 0.5187(6) 0.2380(5) 0.0557(15) Uani 1 1 d . . . . .
N1 N 0.8163(12) 0.4775(5) 0.1324(4) 0.0532(12) Uani 1 1 d . . . . .
H1 H 0.925(11) 0.521(4) 0.098(3) 0.026(12) Uiso 1 1 d . . . . .
C11 C 0.9114(13) 0.6911(5) 0.3821(4) 0.0514(14) Uani 1 1 d . . . . .
C12 C 1.0438(14) 0.6411(5) 0.4574(4) 0.0576(15) Uani 1 1 d . . . . .
H12 H 1.1321 0.5646 0.4371 0.069 Uiso 1 1 calc R U . . .
C13 C 1.0445(13) 0.7056(6) 0.5634(5) 0.0575(15) Uani 1 1 d . . . . .
H13 H 1.1274 0.6722 0.6155 0.069 Uiso 1 1 calc R U . . .
C14 C 0.9222(13) 0.8186(6) 0.5902(5) 0.0577(16) Uani 1 1 d . . . . .
C15 C 0.7896(15) 0.8698(6) 0.5161(5) 0.0633(16) Uani 1 1 d . . . . .
H15 H 0.7034 0.9467 0.5369 0.076 Uiso 1 1 calc R U . . .
C16 C 0.7859(14) 0.8051(5) 0.4094(5) 0.0580(15) Uani 1 1 d . . . . .
H16 H 0.7001 0.8382 0.3575 0.070 Uiso 1 1 calc R U . . .
C21 C 0.6986(13) 0.3662(5) 0.0649(4) 0.0508(14) Uani 1 1 d . . . . .
N22 N 0.7737(11) 0.3528(5) -0.0357(4) 0.0590(13) Uani 1 1 d . . . . .
C23 C 0.6701(15) 0.2475(6) -0.1065(5) 0.0641(17) Uani 1 1 d . . . . .
H23 H 0.7190 0.2374 -0.1777 0.077 Uiso 1 1 calc R U . . .
C24 C 0.4972(14) 0.1550(6) -0.0788(5) 0.0646(17) Uani 1 1 d . . . . .
H24 H 0.4318 0.0833 -0.1298 0.078 Uiso 1 1 calc R U . . .
C25 C 0.4227(15) 0.1697(6) 0.0243(5) 0.0659(17) Uani 1 1 d . . . . .
H25 H 0.3048 0.1074 0.0446 0.079 Uiso 1 1 calc R U . . .
C26 C 0.5196(14) 0.2759(6) 0.0996(5) 0.0605(16) Uani 1 1 d . . . . .
H26 H 0.4681 0.2872 0.1708 0.073 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
Cl14 C14 1.745(6) . ?
O1 C1 1.178(7) . ?
O2 C1 1.387(7) . ?
O2 C11 1.395(6) . ?
C1 N1 1.358(7) . ?
N1 C21 1.392(7) . ?
N1 H1 0.86(5) . ?
C11 C16 1.374(8) . ?
C11 C12 1.374(8) . ?
C12 C13 1.383(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.360(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(9) . ?
C15 C16 1.391(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 N22 1.321(7) . ?
C21 C26 1.399(8) . ?
N22 C23 1.347(7) . ?
C23 C24 1.361(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.349(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.375(8) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C11 117.4(4) . . ?
O1 C1 N1 128.3(6) . . ?
O1 C1 O2 124.5(5) . . ?
N1 C1 O2 107.2(5) . . ?
C1 N1 C21 126.5(5) . . ?
C1 N1 H1 123(3) . . ?
C21 N1 H1 111(3) . . ?
C16 C11 C12 121.6(5) . . ?
C16 C11 O2 116.8(5) . . ?
C12 C11 O2 121.4(5) . . ?
C11 C12 C13 119.5(6) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 118.9(6) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 122.3(6) . . ?
C13 C14 Cl14 119.4(5) . . ?
C15 C14 Cl14 118.2(5) . . ?
C14 C15 C16 119.0(6) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C11 C16 C15 118.7(6) . . ?
C11 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
N22 C21 N1 113.8(5) . . ?
N22 C21 C26 122.6(5) . . ?
N1 C21 C26 123.6(5) . . ?
C21 N22 C23 117.7(5) . . ?
N22 C23 C24 123.1(6) . . ?
N22 C23 H23 118.4 . . ?
C24 C23 H23 118.4 . . ?
C25 C24 C23 118.6(6) . . ?
C25 C24 H24 120.7 . . ?
C23 C24 H24 120.7 . . ?
C24 C25 C26 120.5(6) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C21 117.4(6) . . ?
C25 C26 H26 121.3 . . ?
C21 C26 H26 121.3 . . ?

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
C11 O2 C1 O1 0.9(8) . . . . ?
C11 O2 C1 N1 -177.5(5) . . . . ?
O1 C1 N1 C21 1.0(10) . . . . ?
O2 C1 N1 C21 179.4(5) . . . . ?
C1 O2 C11 C16 -124.8(5) . . . . ?
C1 O2 C11 C12 60.4(7) . . . . ?
C16 C11 C12 C13 1.4(8) . . . . ?
O2 C11 C12 C13 176.0(4) . . . . ?
C11 C12 C13 C14 -1.8(8) . . . . ?
C12 C13 C14 C15 1.7(8) . . . . ?
C12 C13 C14 Cl14 -179.5(4) . . . . ?
C13 C14 C15 C16 -1.3(8) . . . . ?
Cl14 C14 C15 C16 179.9(4) . . . . ?
C12 C11 C16 C15 -1.0(8) . . . . ?
O2 C11 C16 C15 -175.8(4) . . . . ?
C14 C15 C16 C11 0.9(8) . . . . ?
C1 N1 C21 N22 175.6(5) . . . . ?
C1 N1 C21 C26 -4.9(9) . . . . ?
N1 C21 N22 C23 179.8(5) . . . . ?
C26 C21 N22 C23 0.3(8) . . . . ?
C21 N22 C23 C24 -0.8(9) . . . . ?
N22 C23 C24 C25 0.6(9) . . . . ?
C23 C24 C25 C26 0.0(9) . . . . ?
C24 C25 C26 C21 -0.5(9) . . . . ?
N22 C21 C26 C25 0.3(8) . . . . ?
N1 C21 C26 C25 -179.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
N1 H1 N22 0.86(5) 2.15(5) 3.001(7) 170(4) 2_765 yes
C23 H23 O2 0.93 2.57 3.267(8) 133 2_765 yes
C26 H26 O1 0.93 2.29 2.872(7) 121 . yes
C13 H13 O1 0.93 2.53 3.425(8) 163 2_766 yes



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform:acetone'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_CopBr_[12-020]
_database_code_depnum_ccdc_archive 'CCDC 1829156'
loop_
_audit_author_name
_audit_author_address
'John Gallagher'
;Dublin City University
Republic of Ireland
;
_audit_update_record             
;
2018-03-12 deposited with the CCDC.	2019-05-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_CopBr_[12-020]      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      60.00 Degree
RESPONSE: Data collected on weak diffractor using Cu radiation
;
# Added during the CSD deposition process: Monday 12 March 2018 05:37 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4-Bromophenyl-N-2-pyridylcarbamate
_chemical_name_common            CopBr
_chemical_melting_point          469
_chemical_formula_moiety         'C12 H9 Br N2 O2'
_chemical_formula_sum            'C12 H9 Br N2 O2'
_chemical_formula_weight         293.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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/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                   11.349(6)
_cell_length_b                   3.9443(16)
_cell_length_c                   26.137(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.34(5)
_cell_angle_gamma                90
_cell_volume                     1147.2(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    728
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      60.67

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    4.825
_shelx_estimated_absorpt_T_min   0.188
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.487
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Empirical SCALE3 ABSPACK'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      294(1)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         4182
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.0560
_diffrn_reflns_number            4128
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.449
_diffrn_reflns_theta_max         61.181
_diffrn_reflns_theta_full        60.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             1718
_reflns_number_gt                1169
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7

_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)+(0.1288P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1718
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.2152
_refine_ls_wR_factor_gt          0.1876
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.127

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 0.53923(11) 0.4638(2) 0.14544(3) 0.0986(6) Uani 1 1 d . . . . .
O1 O 0.3237(5) 0.4737(14) 0.3600(2) 0.0814(16) Uani 1 1 d . . . . .
C1 C 0.3996(6) 0.2974(18) 0.3851(3) 0.0611(16) Uani 1 1 d . . . . .
N1 N 0.4109(6) 0.2033(16) 0.4359(2) 0.0626(14) Uani 1 1 d . . . . .
H1 H 0.470(7) 0.062(19) 0.444(3) 0.07(2) Uiso 1 1 d . . . . .
O2 O 0.4947(4) 0.1581(14) 0.36653(17) 0.0696(13) Uani 1 1 d . . . . .
C11 C 0.5001(6) 0.2336(17) 0.3146(2) 0.0599(16) Uani 1 1 d . . . . .
C12 C 0.6012(6) 0.3885(18) 0.3052(3) 0.0633(17) Uani 1 1 d . . . . .
H12 H 0.6621 0.4499 0.3330 0.076 Uiso 1 1 calc R U . . .
C13 C 0.6134(7) 0.4540(18) 0.2550(3) 0.0678(18) Uani 1 1 d . . . . .
H13 H 0.6820 0.5611 0.2485 0.081 Uiso 1 1 calc R U . . .
C14 C 0.5247(7) 0.3612(16) 0.2150(3) 0.0638(17) Uani 1 1 d . . . . .
C15 C 0.4221(6) 0.2030(19) 0.2231(3) 0.0672(17) Uani 1 1 d . . . . .
H15 H 0.3614 0.1457 0.1951 0.081 Uiso 1 1 calc R U . . .
C16 C 0.4104(6) 0.1302(19) 0.2737(3) 0.0625(16) Uani 1 1 d . . . . .
H16 H 0.3434 0.0139 0.2800 0.075 Uiso 1 1 calc R U . . .
C21 C 0.3332(6) 0.2966(17) 0.4688(2) 0.0582(15) Uani 1 1 d . . . . .
N22 N 0.3718(5) 0.1952(14) 0.5176(2) 0.0613(14) Uani 1 1 d . . . . .
C23 C 0.3013(7) 0.2730(19) 0.5523(3) 0.0688(18) Uani 1 1 d . . . . .
H23 H 0.3271 0.2043 0.5867 0.083 Uiso 1 1 calc R U . . .
C24 C 0.1960(7) 0.4435(18) 0.5402(3) 0.0701(19) Uani 1 1 d . . . . .
H24 H 0.1502 0.4880 0.5653 0.084 Uiso 1 1 calc R U . . .
C25 C 0.1594(7) 0.5487(18) 0.4893(3) 0.0687(18) Uani 1 1 d . . . . .
H25 H 0.0889 0.6732 0.4798 0.082 Uiso 1 1 calc R U . . .
C26 C 0.2259(6) 0.4716(18) 0.4524(3) 0.0650(17) Uani 1 1 d . . . . .
H26 H 0.2003 0.5338 0.4177 0.078 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 C14 1.902(6) . ?
O1 C1 1.197(8) . ?
C1 N1 1.359(8) . ?
C1 O2 1.382(8) . ?
N1 C21 1.398(8) . ?
N1 H1 0.86(8) . ?
O2 C11 1.402(7) . ?
C11 C12 1.364(9) . ?
C11 C16 1.386(9) . ?
C12 C13 1.371(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.351(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(10) . ?
C15 C16 1.383(9) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C21 N22 1.326(8) . ?
C21 C26 1.392(10) . ?
N22 C23 1.355(8) . ?
C23 C24 1.354(11) . ?
C23 H23 0.9300 . ?
C24 C25 1.379(11) . ?
C24 H24 0.9300 . ?
C25 C26 1.370(10) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 127.9(6) . . ?
O1 C1 O2 124.4(6) . . ?
N1 C1 O2 107.7(6) . . ?
C1 N1 C21 125.4(7) . . ?
C1 N1 H1 109(5) . . ?
C21 N1 H1 125(5) . . ?
C1 O2 C11 116.2(5) . . ?
C12 C11 C16 120.6(6) . . ?
C12 C11 O2 117.9(6) . . ?
C16 C11 O2 121.3(6) . . ?
C11 C12 C13 120.3(6) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.3(7) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 121.9(6) . . ?
C13 C14 Br1 119.4(5) . . ?
C15 C14 Br1 118.7(5) . . ?
C14 C15 C16 119.0(6) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C15 C16 C11 118.9(6) . . ?
C15 C16 H16 120.6 . . ?
C11 C16 H16 120.6 . . ?
N22 C21 C26 123.3(6) . . ?
N22 C21 N1 112.6(6) . . ?
C26 C21 N1 124.1(6) . . ?
C21 N22 C23 116.6(6) . . ?
C24 C23 N22 124.5(7) . . ?
C24 C23 H23 117.7 . . ?
N22 C23 H23 117.7 . . ?
C23 C24 C25 117.3(6) . . ?
C23 C24 H24 121.4 . . ?
C25 C24 H24 121.4 . . ?
C26 C25 C24 120.7(7) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C21 117.5(7) . . ?
C25 C26 H26 121.2 . . ?
C21 C26 H26 121.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N1 C21 0.5(12) . . . . ?
O2 C1 N1 C21 179.1(6) . . . . ?
O1 C1 O2 C11 0.0(11) . . . . ?
N1 C1 O2 C11 -178.7(6) . . . . ?
C1 O2 C11 C12 122.1(7) . . . . ?
C1 O2 C11 C16 -63.1(9) . . . . ?
C16 C11 C12 C13 2.2(11) . . . . ?
O2 C11 C12 C13 177.0(6) . . . . ?
C11 C12 C13 C14 -0.5(11) . . . . ?
C12 C13 C14 C15 0.1(11) . . . . ?
C12 C13 C14 Br1 178.1(5) . . . . ?
C13 C14 C15 C16 -1.4(11) . . . . ?
Br1 C14 C15 C16 -179.4(5) . . . . ?
C14 C15 C16 C11 3.0(11) . . . . ?
C12 C11 C16 C15 -3.4(11) . . . . ?
O2 C11 C16 C15 -178.1(6) . . . . ?
C1 N1 C21 N22 -174.1(6) . . . . ?
C1 N1 C21 C26 6.9(11) . . . . ?
C26 C21 N22 C23 -0.6(10) . . . . ?
N1 C21 N22 C23 -179.6(6) . . . . ?
C21 N22 C23 C24 0.2(10) . . . . ?
N22 C23 C24 C25 -1.0(11) . . . . ?
C23 C24 C25 C26 2.2(11) . . . . ?
C24 C25 C26 C21 -2.5(11) . . . . ?
N22 C21 C26 C25 1.8(10) . . . . ?
N1 C21 C26 C25 -179.4(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
N1 H1 N22 0.86(8) 2.14(8) 2.975(8) 163(7) 3_656 yes
C15 H15 O1 0.93 2.40 3.307(9) 165 2_545 yes
C23 H23 O2 0.93 2.58 3.290(9) 134 3_656 yes
C26 H26 O1 0.93 2.26 2.850(9) 121 . yes




#============================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Tetrahydrofuran'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_CmmBr_[13-022]
_database_code_depnum_ccdc_archive 'CCDC 1829153'
loop_
_audit_author_name
_audit_author_address
'John Gallagher'
;Dublin City University
Republic of Ireland
;
_audit_update_record             
;
2018-03-12 deposited with the CCDC.	2019-05-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_CmmBr_[13-022]      
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        26% Check
RESPONSE: This crystal structure was twinned
;
_vrf_PLAT029_CmmBr_[13-022]      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.924 Why?
RESPONSE: This crystal structure was twinned
;
# Added during the CSD deposition process: Monday 12 March 2018 05:37 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        3-Bromophenyl-N-3-pyridylcarbamate
_chemical_name_common            CmmBr
_chemical_melting_point          427
_chemical_formula_moiety         'C12 H9 Br N2 O2'
_chemical_formula_sum            'C12 H9 Br N2 O2'
_chemical_formula_weight         293.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   3.8827(5)
_cell_length_b                   24.756(2)
_cell_length_c                   17.742(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.789(14)
_cell_angle_gamma                90
_cell_volume                     1704.5(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1096
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      22.03

_exptl_crystal_description       Trapezoid
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_F_000             876
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    3.607
_shelx_estimated_absorpt_T_min   0.411
_shelx_estimated_absorpt_T_max   0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   'Empirical SCALE3 ABSPACK'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         99999
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_diffrn_detector_area_resol_mean 16.056
_diffrn_reflns_number            10527
_diffrn_reflns_av_unetI/netI     0.4197
_diffrn_reflns_av_R_equivalents  0.1052
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.598
_diffrn_reflns_theta_max         27.931
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measured_fraction_theta_full 0.924
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_Laue_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.735
_diffrn_reflns_point_group_measured_fraction_full 0.812
_reflns_number_total             5993
_reflns_number_gt                1546
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_max     0.606
_reflns_Friedel_fraction_full    0.694

_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7
_refine_special_details          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)+(0.0185P)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_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.008(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5993
_refine_ls_number_parameters     460
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.2284
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.0958
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   0.630
_refine_ls_restrained_S_all      0.630
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.078

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
Br1A Br 1.0690(3) 0.21564(13) 0.88050(10) 0.0701(6) Uani 1 1 d . . . . .
O1A O 1.482(3) 0.0160(6) 0.9105(8) 0.067(4) Uani 1 1 d . U . . .
O2A O 1.202(3) 0.0141(5) 0.7960(7) 0.060(3) Uani 1 1 d . U . . .
N1A N 1.263(3) -0.0636(6) 0.8597(8) 0.059(4) Uani 1 1 d . . . . .
H1A H 1.1709 -0.0774 0.8194 0.071 Uiso 1 1 calc R U . . .
C1A C 1.334(5) -0.0097(9) 0.8618(14) 0.061(5) Uani 1 1 d . . . . .
C11A C 1.280(4) 0.0661(9) 0.7834(11) 0.054(5) Uani 1 1 d . U . . .
C12A C 1.160(4) 0.1069(8) 0.8334(10) 0.054(5) Uani 1 1 d . . . . .
H12A H 1.0500 0.0982 0.8776 0.065 Uiso 1 1 calc R U . . .
C13A C 1.216(4) 0.1597(9) 0.8129(11) 0.053(5) Uani 1 1 d . . . . .
C14A C 1.379(4) 0.1758(8) 0.7499(12) 0.061(5) Uani 1 1 d . . . . .
H14A H 1.4144 0.2122 0.7401 0.073 Uiso 1 1 calc R U . . .
C15A C 1.492(4) 0.1356(10) 0.6999(13) 0.073(7) Uani 1 1 d . . . . .
H15A H 1.6100 0.1451 0.6570 0.087 Uiso 1 1 calc R U . . .
C16A C 1.427(4) 0.0827(9) 0.7155(10) 0.063(5) Uani 1 1 d . U . . .
H16A H 1.4815 0.0567 0.6801 0.075 Uiso 1 1 calc R U . . .
C21A C 1.337(4) -0.0966(8) 0.9209(11) 0.049(5) Uani 1 1 d . U . . .
C22A C 1.302(4) -0.0822(7) 0.9954(12) 0.055(5) Uani 1 1 d . U . . .
H22A H 1.2253 -0.0474 1.0053 0.066 Uiso 1 1 calc R U . . .
N23A N 1.368(3) -0.1138(7) 1.0533(9) 0.062(4) Uani 1 1 d . . . . .
C24A C 1.483(4) -0.1649(7) 1.0395(12) 0.057(5) Uani 1 1 d . . . . .
H24A H 1.5216 -0.1883 1.0799 0.068 Uiso 1 1 calc R U . . .
C25A C 1.541(5) -0.1824(8) 0.9695(15) 0.073(6) Uani 1 1 d . . . . .
H25A H 1.6286 -0.2169 0.9614 0.087 Uiso 1 1 calc R U . . .
C26A C 1.470(4) -0.1485(10) 0.9105(13) 0.074(7) Uani 1 1 d . . . . .
H26A H 1.5109 -0.1603 0.8618 0.088 Uiso 1 1 calc R U . . .
Br1B Br 0.2077(3) 0.21304(12) 0.53397(10) 0.0637(5) Uani 1 1 d . . . . .
O1B O 0.800(3) 0.0211(6) 0.5770(8) 0.060(4) Uani 1 1 d . . . . .
O2B O 0.477(3) 0.0101(6) 0.4701(7) 0.057(4) Uani 1 1 d . . . . .
C1B C 0.646(4) -0.0068(8) 0.5357(11) 0.049(4) Uani 1 1 d . . . . .
N1B N 0.627(3) -0.0626(7) 0.5375(9) 0.054(4) Uani 1 1 d . . . . .
H1B H 0.5168 -0.0782 0.5008 0.065 Uiso 1 1 calc R U . . .
C11B C 0.508(4) 0.0635(8) 0.4505(12) 0.052(5) Uani 1 1 d . . . . .
C12B C 0.366(3) 0.1047(7) 0.4993(9) 0.046(4) Uani 1 1 d . . . . .
H12B H 0.2737 0.0964 0.5457 0.055 Uiso 1 1 calc R U . . .
C13B C 0.379(3) 0.1566(8) 0.4725(11) 0.047(5) Uani 1 1 d . . . . .
C14B C 0.520(4) 0.1701(6) 0.4043(11) 0.051(5) Uani 1 1 d . . . . .
H14B H 0.5302 0.2060 0.3888 0.061 Uiso 1 1 calc R U . . .
C15B C 0.646(4) 0.1295(10) 0.3602(11) 0.058(6) Uani 1 1 d . . . . .
H15B H 0.7415 0.1384 0.3144 0.070 Uiso 1 1 calc R U . . .
C16B C 0.636(4) 0.0776(10) 0.3808(10) 0.055(5) Uani 1 1 d . . . . .
H16B H 0.7143 0.0510 0.3485 0.066 Uiso 1 1 calc R U . . .
C21B C 0.769(4) -0.0948(7) 0.5924(11) 0.048(4) Uani 1 1 d . . . . .
C22B C 0.883(4) -0.0769(7) 0.6647(10) 0.052(4) Uani 1 1 d . . . . .
H22B H 0.8646 -0.0402 0.6755 0.063 Uiso 1 1 calc R U . . .
N23B N 1.015(4) -0.1090(8) 0.7184(10) 0.067(5) Uani 1 1 d . . . . .
C24B C 1.050(4) -0.1620(10) 0.6983(12) 0.064(6) Uani 1 1 d . . . . .
H24B H 1.1473 -0.1855 0.7339 0.077 Uiso 1 1 calc R U . . .
C25B C 0.953(4) -0.1825(8) 0.6311(12) 0.066(6) Uani 1 1 d . . . . .
H25B H 0.9822 -0.2190 0.6210 0.079 Uiso 1 1 calc R U . . .
C26B C 0.810(4) -0.1485(8) 0.5772(10) 0.053(5) Uani 1 1 d . . . . .
H26B H 0.7405 -0.1622 0.5303 0.064 Uiso 1 1 calc R U . . .
Br1C Br 0.1846(4) 0.21445(15) 0.20145(11) 0.0715(5) Uani 1 1 d . . . . .
O1C O -0.013(3) 0.0070(6) 0.2545(9) 0.074(4) Uani 1 1 d . . . . .
O2C O 0.151(3) 0.0081(5) 0.1329(7) 0.063(4) Uani 1 1 d . . . . .
N1C N 0.217(3) -0.0671(7) 0.2007(10) 0.073(5) Uani 1 1 d . . . . .
H1C H 0.2734 -0.0802 0.1579 0.088 Uiso 1 1 calc R U . . .
C1C C 0.118(4) -0.0134(8) 0.2045(13) 0.052(5) Uani 1 1 d . . . . .
C11C C 0.040(4) 0.0590(8) 0.1205(12) 0.055(5) Uani 1 1 d . . . . .
C12C C 0.140(4) 0.1032(8) 0.1642(10) 0.053(5) Uani 1 1 d . . . . .
H12C H 0.2706 0.0987 0.2086 0.064 Uiso 1 1 calc R U . . .
C13C C 0.044(4) 0.1525(8) 0.1407(12) 0.060(6) Uani 1 1 d . . . . .
C14C C -0.137(4) 0.1630(8) 0.0739(11) 0.057(5) Uani 1 1 d . . . . .
H14C H -0.1874 0.1981 0.0585 0.069 Uiso 1 1 calc R U . . .
C15C C -0.240(5) 0.1186(10) 0.0309(11) 0.060(6) Uani 1 1 d . . . . .
H15C H -0.3823 0.1237 -0.0117 0.072 Uiso 1 1 calc R U . . .
C16C C -0.140(4) 0.0692(10) 0.0498(11) 0.061(5) Uani 1 1 d . . . . .
H16C H -0.1859 0.0407 0.0169 0.073 Uiso 1 1 calc R U . . .
C21C C 0.230(4) -0.1018(8) 0.2665(12) 0.048(5) Uani 1 1 d . . . . .
C22C C 0.311(4) -0.0822(8) 0.3370(12) 0.064(5) Uani 1 1 d . . . . .
H22C H 0.3623 -0.0458 0.3433 0.077 Uiso 1 1 calc R U . . .
N23C N 0.319(4) -0.1152(7) 0.3971(9) 0.068(5) Uani 1 1 d . . . . .
C24C C 0.249(4) -0.1674(8) 0.3860(12) 0.054(5) Uani 1 1 d . . . . .
H24C H 0.2648 -0.1910 0.4267 0.065 Uiso 1 1 calc R U . . .
C25C C 0.160(4) -0.1864(9) 0.3186(13) 0.062(6) Uani 1 1 d . . . . .
H25C H 0.1105 -0.2230 0.3132 0.074 Uiso 1 1 calc R U . . .
C26C C 0.139(4) -0.1541(9) 0.2580(11) 0.065(6) Uani 1 1 d . . . . .
H26C H 0.0629 -0.1674 0.2113 0.077 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
Br1A C13A 1.930(17) . ?
O1A C1A 1.20(2) . ?
O2A C11A 1.34(2) . ?
O2A C1A 1.39(2) . ?
N1A C1A 1.36(2) . ?
N1A C21A 1.38(2) . ?
N1A H1A 0.8600 . ?
C11A C16A 1.41(2) . ?
C11A C12A 1.43(2) . ?
C12A C13A 1.38(2) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.36(2) . ?
C14A C15A 1.41(2) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.36(3) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C21A C22A 1.38(2) . ?
C21A C26A 1.40(2) . ?
C22A N23A 1.31(2) . ?
C22A H22A 0.9300 . ?
N23A C24A 1.37(2) . ?
C24A C25A 1.34(2) . ?
C24A H24A 0.9300 . ?
C25A C26A 1.36(3) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
Br1B C13B 1.906(17) . ?
O1B C1B 1.160(19) . ?
O2B C11B 1.37(2) . ?
O2B C1B 1.38(2) . ?
C1B N1B 1.38(2) . ?
N1B C21B 1.36(2) . ?
N1B H1B 0.8600 . ?
C11B C16B 1.39(2) . ?
C11B C12B 1.46(2) . ?
C12B C13B 1.37(2) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.39(2) . ?
C14B C15B 1.37(2) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.34(2) . ?
C15B H15B 0.9300 . ?
C16B H16B 0.9300 . ?
C21B C26B 1.37(2) . ?
C21B C22B 1.42(2) . ?
C22B N23B 1.33(2) . ?
C22B H22B 0.9300 . ?
N23B C24B 1.37(2) . ?
C24B C25B 1.34(2) . ?
C24B H24B 0.9300 . ?
C25B C26B 1.38(2) . ?
C25B H25B 0.9300 . ?
C26B H26B 0.9300 . ?
Br1C C13C 1.943(17) . ?
O1C C1C 1.15(2) . ?
O2C C11C 1.35(2) . ?
O2C C1C 1.39(2) . ?
N1C C1C 1.39(2) . ?
N1C C21C 1.45(2) . ?
N1C H1C 0.8600 . ?
C11C C12C 1.39(2) . ?
C11C C16C 1.44(2) . ?
C12C C13C 1.34(2) . ?
C12C H12C 0.9300 . ?
C13C C14C 1.38(2) . ?
C14C C15C 1.39(2) . ?
C14C H14C 0.9300 . ?
C15C C16C 1.33(2) . ?
C15C H15C 0.9300 . ?
C16C H16C 0.9300 . ?
C21C C26C 1.35(2) . ?
C21C C22C 1.37(2) . ?
C22C N23C 1.34(2) . ?
C22C H22C 0.9300 . ?
N23C C24C 1.33(2) . ?
C24C C25C 1.32(2) . ?
C24C H24C 0.9300 . ?
C25C C26C 1.34(2) . ?
C25C H25C 0.9300 . ?
C26C H26C 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11A O2A C1A 117.9(16) . . ?
C1A N1A C21A 121.3(18) . . ?
C1A N1A H1A 119.3 . . ?
C21A N1A H1A 119.3 . . ?
O1A C1A N1A 129(2) . . ?
O1A C1A O2A 122.3(19) . . ?
N1A C1A O2A 109(2) . . ?
O2A C11A C16A 121.4(19) . . ?
O2A C11A C12A 119.7(18) . . ?
C16A C11A C12A 118(2) . . ?
C13A C12A C11A 116.7(17) . . ?
C13A C12A H12A 121.6 . . ?
C11A C12A H12A 121.6 . . ?
C14A C13A C12A 125.2(17) . . ?
C14A C13A Br1A 117.1(17) . . ?
C12A C13A Br1A 117.6(15) . . ?
C13A C14A C15A 118.2(18) . . ?
C13A C14A H14A 120.9 . . ?
C15A C14A H14A 120.9 . . ?
C16A C15A C14A 119(2) . . ?
C16A C15A H15A 120.5 . . ?
C14A C15A H15A 120.5 . . ?
C15A C16A C11A 122(2) . . ?
C15A C16A H16A 118.8 . . ?
C11A C16A H16A 118.8 . . ?
C22A C21A N1A 125.2(18) . . ?
C22A C21A C26A 114.3(19) . . ?
N1A C21A C26A 120.5(19) . . ?
N23A C22A C21A 125.1(19) . . ?
N23A C22A H22A 117.5 . . ?
C21A C22A H22A 117.5 . . ?
C22A N23A C24A 117.9(18) . . ?
C25A C24A N23A 122.1(18) . . ?
C25A C24A H24A 119.0 . . ?
N23A C24A H24A 119.0 . . ?
C24A C25A C26A 118(2) . . ?
C24A C25A H25A 120.8 . . ?
C26A C25A H25A 120.8 . . ?
C25A C26A C21A 122(2) . . ?
C25A C26A H26A 119.0 . . ?
C21A C26A H26A 119.0 . . ?
C11B O2B C1B 117.5(15) . . ?
O1B C1B N1B 127(2) . . ?
O1B C1B O2B 125.0(19) . . ?
N1B C1B O2B 107.3(17) . . ?
C21B N1B C1B 125.5(17) . . ?
C21B N1B H1B 117.3 . . ?
C1B N1B H1B 117.3 . . ?
O2B C11B C16B 120.2(18) . . ?
O2B C11B C12B 119.1(17) . . ?
C16B C11B C12B 120.3(19) . . ?
C13B C12B C11B 115.5(16) . . ?
C13B C12B H12B 122.2 . . ?
C11B C12B H12B 122.2 . . ?
C12B C13B C14B 123.4(16) . . ?
C12B C13B Br1B 118.1(14) . . ?
C14B C13B Br1B 118.5(14) . . ?
C15B C14B C13B 118.5(18) . . ?
C15B C14B H14B 120.7 . . ?
C13B C14B H14B 120.7 . . ?
C16B C15B C14B 122.3(19) . . ?
C16B C15B H15B 118.8 . . ?
C14B C15B H15B 118.8 . . ?
C15B C16B C11B 119.9(19) . . ?
C15B C16B H16B 120.1 . . ?
C11B C16B H16B 120.1 . . ?
N1B C21B C26B 118.4(18) . . ?
N1B C21B C22B 125.0(17) . . ?
C26B C21B C22B 116.6(18) . . ?
N23B C22B C21B 124.3(17) . . ?
N23B C22B H22B 117.8 . . ?
C21B C22B H22B 117.8 . . ?
C22B N23B C24B 115.3(17) . . ?
C25B C24B N23B 124.6(19) . . ?
C25B C24B H24B 117.7 . . ?
N23B C24B H24B 117.7 . . ?
C24B C25B C26B 118.9(19) . . ?
C24B C25B H25B 120.5 . . ?
C26B C25B H25B 120.5 . . ?
C21B C26B C25B 120.3(19) . . ?
C21B C26B H26B 119.9 . . ?
C25B C26B H26B 119.9 . . ?
C11C O2C C1C 118.0(15) . . ?
C1C N1C C21C 122.2(18) . . ?
C1C N1C H1C 118.9 . . ?
C21C N1C H1C 118.9 . . ?
O1C C1C O2C 126.4(19) . . ?
O1C C1C N1C 126(2) . . ?
O2C C1C N1C 106.9(19) . . ?
O2C C11C C12C 124.3(17) . . ?
O2C C11C C16C 116.8(19) . . ?
C12C C11C C16C 117.8(17) . . ?
C13C C12C C11C 118.3(17) . . ?
C13C C12C H12C 120.9 . . ?
C11C C12C H12C 120.9 . . ?
C12C C13C C14C 124.6(18) . . ?
C12C C13C Br1C 118.4(17) . . ?
C14C C13C Br1C 117.0(16) . . ?
C13C C14C C15C 116.8(18) . . ?
C13C C14C H14C 121.6 . . ?
C15C C14C H14C 121.6 . . ?
C16C C15C C14C 120.9(18) . . ?
C16C C15C H15C 119.5 . . ?
C14C C15C H15C 119.5 . . ?
C15C C16C C11C 121.0(19) . . ?
C15C C16C H16C 119.5 . . ?
C11C C16C H16C 119.5 . . ?
C26C C21C C22C 120(2) . . ?
C26C C21C N1C 118.5(18) . . ?
C22C C21C N1C 121.8(19) . . ?
N23C C22C C21C 120.7(19) . . ?
N23C C22C H22C 119.6 . . ?
C21C C22C H22C 119.6 . . ?
C24C N23C C22C 118.1(18) . . ?
C25C C24C N23C 121.8(19) . . ?
C25C C24C H24C 119.1 . . ?
N23C C24C H24C 119.1 . . ?
C24C C25C C26C 121(2) . . ?
C24C C25C H25C 119.3 . . ?
C26C C25C H25C 119.3 . . ?
C25C C26C C21C 118(2) . . ?
C25C C26C H26C 120.9 . . ?
C21C C26C H26C 120.9 . . ?

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
C21A N1A C1A O1A 6(3) . . . . ?
C21A N1A C1A O2A -174.2(13) . . . . ?
C11A O2A C1A O1A 8(2) . . . . ?
C11A O2A C1A N1A -172.5(13) . . . . ?
C1A O2A C11A C16A 126.6(17) . . . . ?
C1A O2A C11A C12A -64.1(18) . . . . ?
O2A C11A C12A C13A -173.2(14) . . . . ?
C16A C11A C12A C13A -3(2) . . . . ?
C11A C12A C13A C14A -1(2) . . . . ?
C11A C12A C13A Br1A -178.4(10) . . . . ?
C12A C13A C14A C15A 2(3) . . . . ?
Br1A C13A C14A C15A 179.3(12) . . . . ?
C13A C14A C15A C16A 2(3) . . . . ?
C14A C15A C16A C11A -6(3) . . . . ?
O2A C11A C16A C15A 176.7(15) . . . . ?
C12A C11A C16A C15A 7(3) . . . . ?
C1A N1A C21A C22A 38(2) . . . . ?
C1A N1A C21A C26A -140.2(18) . . . . ?
N1A C21A C22A N23A 179.1(16) . . . . ?
C26A C21A C22A N23A -3(3) . . . . ?
C21A C22A N23A C24A 0(3) . . . . ?
C22A N23A C24A C25A 3(3) . . . . ?
N23A C24A C25A C26A -3(3) . . . . ?
C24A C25A C26A C21A 0(3) . . . . ?
C22A C21A C26A C25A 3(3) . . . . ?
N1A C21A C26A C25A -179.1(17) . . . . ?
C11B O2B C1B O1B 3(3) . . . . ?
C11B O2B C1B N1B -170.3(13) . . . . ?
O1B C1B N1B C21B 5(3) . . . . ?
O2B C1B N1B C21B 178.6(14) . . . . ?
C1B O2B C11B C16B 123.1(17) . . . . ?
C1B O2B C11B C12B -64.3(19) . . . . ?
O2B C11B C12B C13B -174.2(14) . . . . ?
C16B C11B C12B C13B -2(2) . . . . ?
C11B C12B C13B C14B -1(2) . . . . ?
C11B C12B C13B Br1B -178.7(10) . . . . ?
C12B C13B C14B C15B 2(2) . . . . ?
Br1B C13B C14B C15B 179.5(11) . . . . ?
C13B C14B C15B C16B 0(3) . . . . ?
C14B C15B C16B C11B -3(3) . . . . ?
O2B C11B C16B C15B 176.1(15) . . . . ?
C12B C11B C16B C15B 4(2) . . . . ?
C1B N1B C21B C26B -162.7(15) . . . . ?
C1B N1B C21B C22B 16(3) . . . . ?
N1B C21B C22B N23B 178.7(16) . . . . ?
C26B C21B C22B N23B -2(2) . . . . ?
C21B C22B N23B C24B 3(2) . . . . ?
C22B N23B C24B C25B -2(2) . . . . ?
N23B C24B C25B C26B 0(3) . . . . ?
N1B C21B C26B C25B 179.8(15) . . . . ?
C22B C21B C26B C25B 1(2) . . . . ?
C24B C25B C26B C21B 0(3) . . . . ?
C11C O2C C1C O1C 4(3) . . . . ?
C11C O2C C1C N1C 174.2(14) . . . . ?
C21C N1C C1C O1C -13(3) . . . . ?
C21C N1C C1C O2C 177.3(13) . . . . ?
C1C O2C C11C C12C 53(2) . . . . ?
C1C O2C C11C C16C -139.4(16) . . . . ?
O2C C11C C12C C13C 172.2(14) . . . . ?
C16C C11C C12C C13C 4(2) . . . . ?
C11C C12C C13C C14C -3(2) . . . . ?
C11C C12C C13C Br1C -179.8(11) . . . . ?
C12C C13C C14C C15C 4(2) . . . . ?
Br1C C13C C14C C15C -179.4(11) . . . . ?
C13C C14C C15C C16C -6(3) . . . . ?
C14C C15C C16C C11C 8(3) . . . . ?
O2C C11C C16C C15C -176.0(16) . . . . ?
C12C C11C C16C C15C -7(3) . . . . ?
C1C N1C C21C C26C 143.6(17) . . . . ?
C1C N1C C21C C22C -32(2) . . . . ?
C26C C21C C22C N23C 3(3) . . . . ?
N1C C21C C22C N23C 179.5(14) . . . . ?
C21C C22C N23C C24C 1(3) . . . . ?
C22C N23C C24C C25C -3(3) . . . . ?
N23C C24C C25C C26C 1(3) . . . . ?
C24C C25C C26C C21C 4(3) . . . . ?
C22C C21C C26C C25C -6(3) . . . . ?
N1C C21C C26C C25C 178.1(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
#   C24A H24A Br1A  0.93      2.93      3.692(18) 140       2_847  yes
#   C24B H24B Br1C  0.93      3.03      3.67(2)   127       2_646  yes
#   C16C H16C O1A   0.93      3.43      3.84(2)   110       ?      yes
#   C24C H24C Br1B  0.93      3.09      3.754(17) 129       2_546  yes
N1A H1A N23B 0.86 2.03 2.88(2) 172 . yes
C16A H16A O1B 0.93 2.41 3.27(2) 154 1_655 yes
N1B H1B N23C 0.86 2.17 3.02(2) 170 . yes
C16B H16B O1C 0.93 2.28 3.18(2) 163 1_655 yes
N1C H1C N23A 0.86 2.08 2.94(2) 176 1_454 yes
C22B H22B O1B 0.93 2.32 2.89(2) 119 . yes



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform:acetonitrile'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_CmpCl_[11-015]
_database_code_depnum_ccdc_archive 'CCDC 1829149'
loop_
_audit_author_name
_audit_author_address
'John Gallagher'
;Dublin City University
Republic of Ireland
;
_audit_update_record             
;
2018-03-12 deposited with the CCDC.	2019-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4-Chlorobenzene-N-3-pyridylcarbamate
_chemical_name_common            CmpCl
_chemical_melting_point          447
_chemical_formula_moiety         'C12 H9 Cl N2 O2'
_chemical_formula_sum            'C12 H9 Cl N2 O2'
_chemical_formula_weight         248.66

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.9792(3)
_cell_length_b                   3.8079(1)
_cell_length_c                   23.0781(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.036(2)
_cell_angle_gamma                90
_cell_volume                     1136.20(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    3921
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.40

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.326
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_process_details   '(ABSFAC, Clark and Reid, 1998)'
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      294(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Xcalibur, Sapphire3, Gemini Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         7969
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
_diffrn_detector_area_resol_mean 16.056
_diffrn_reflns_number            7270
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.265
_diffrn_reflns_theta_max         27.456
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_point_group_measured_fraction_full 0.881
_reflns_number_total             4260
_reflns_number_gt                3727
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_max     0.691
_reflns_Friedel_fraction_full    0.763

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_solution    'SHELXS-14/7 (Sheldrick, 2014)'
_computing_structure_refinement  
'SHELXL97 and SHELXL-14/7 (Sheldrick, 2008) & SORTX (McArdle, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-14/7

_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)+(0.0678P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x from 1310 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack & Wagner, 2013).
;
_refine_ls_abs_structure_Flack   0.04(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4260
_refine_ls_number_parameters     315
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.046

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
Cl1A Cl 0.45910(9) 0.6212(4) 0.10035(7) 0.0796(5) Uani 1 1 d . . . . .
O1A O 0.0314(2) 0.4247(8) 0.22107(11) 0.0427(7) Uani 1 1 d . . . . .
O2A O 0.01848(19) 0.7295(8) 0.13648(11) 0.0437(7) Uani 1 1 d . . . . .
C1A C -0.0197(3) 0.5861(10) 0.18405(15) 0.0335(8) Uani 1 1 d . . . . .
N1A N -0.1224(2) 0.6541(9) 0.18169(14) 0.0385(7) Uani 1 1 d . . . . .
H1A H -0.150(3) 0.750(10) 0.1525(18) 0.023(9) Uiso 1 1 d . . . . .
C11A C 0.1246(3) 0.6928(10) 0.13064(16) 0.0347(8) Uani 1 1 d . . . . .
C12A C 0.1971(3) 0.8332(11) 0.17127(16) 0.0379(8) Uani 1 1 d . . . . .
H12A H 0.1767 0.9419 0.2045 0.045 Uiso 1 1 calc R U . . .
C13A C 0.3007(3) 0.8102(11) 0.16192(19) 0.0429(9) Uani 1 1 d . . . . .
H13A H 0.3509 0.9029 0.1888 0.051 Uiso 1 1 calc R U . . .
C14A C 0.3285(3) 0.6487(12) 0.1123(2) 0.0446(10) Uani 1 1 d . . . . .
C15A C 0.2558(3) 0.5120(11) 0.07153(18) 0.0448(10) Uani 1 1 d . . . . .
H15A H 0.2760 0.4063 0.0380 0.054 Uiso 1 1 calc R U . . .
C16A C 0.1522(3) 0.5341(11) 0.08116(16) 0.0417(9) Uani 1 1 d . . . . .
H16A H 0.1019 0.4418 0.0542 0.050 Uiso 1 1 calc R U . . .
C21A C -0.1892(3) 0.5476(10) 0.22268(16) 0.0347(8) Uani 1 1 d . . . . .
C22A C -0.1574(3) 0.4181(12) 0.27790(16) 0.0409(9) Uani 1 1 d . . . . .
H22A H -0.0868 0.3943 0.2882 0.049 Uiso 1 1 calc R U . . .
N23A N -0.2225(3) 0.3275(10) 0.31638(14) 0.0439(8) Uani 1 1 d . . . . .
C24A C -0.3232(3) 0.3599(12) 0.30209(19) 0.0467(10) Uani 1 1 d . . . . .
H24A H -0.3690 0.2962 0.3290 0.056 Uiso 1 1 calc R U . . .
C25A C -0.3621(3) 0.4857(13) 0.24831(19) 0.0510(11) Uani 1 1 d . . . . .
H25A H -0.4331 0.5069 0.2394 0.061 Uiso 1 1 calc R U . . .
C26A C -0.2947(3) 0.5790(11) 0.20817(18) 0.0430(9) Uani 1 1 d . . . . .
H26A H -0.3197 0.6621 0.1717 0.052 Uiso 1 1 calc R U . . .
Cl1B Cl 0.46033(9) 1.2035(4) -0.13612(7) 0.0783(5) Uani 1 1 d . . . . .
O1B O 0.0198(2) 1.1880(10) -0.02730(13) 0.0559(9) Uani 1 1 d . . . . .
O2B O 0.0195(2) 0.9340(9) -0.11612(11) 0.0457(7) Uani 1 1 d . . . . .
C1B C -0.0250(3) 1.0326(11) -0.06766(16) 0.0383(8) Uani 1 1 d . . . . .
N1B N -0.1262(2) 0.9468(9) -0.07326(15) 0.0402(8) Uani 1 1 d . . . . .
H1B H -0.149(3) 0.881(11) -0.1049(19) 0.034(11) Uiso 1 1 d . . . . .
C11B C 0.1252(3) 1.0059(11) -0.11795(15) 0.0362(8) Uani 1 1 d . . . . .
C12B C 0.1976(3) 0.8958(11) -0.07483(18) 0.0427(9) Uani 1 1 d . . . . .
H12B H 0.1768 0.7807 -0.0423 0.051 Uiso 1 1 calc R U . . .
C13B C 0.3015(3) 0.9566(13) -0.07996(19) 0.0467(10) Uani 1 1 d . . . . .
H13B H 0.3511 0.8877 -0.0507 0.056 Uiso 1 1 calc R U . . .
C14B C 0.3300(3) 1.1203(11) -0.1290(2) 0.0463(10) Uani 1 1 d . . . . .
C15B C 0.2576(3) 1.2287(12) -0.17233(18) 0.0483(10) Uani 1 1 d . . . . .
H15B H 0.2782 1.3419 -0.2051 0.058 Uiso 1 1 calc R U . . .
C16B C 0.1535(3) 1.1683(12) -0.16686(17) 0.0448(10) Uani 1 1 d . . . . .
H16B H 0.1038 1.2374 -0.1961 0.054 Uiso 1 1 calc R U . . .
C21B C -0.1912(3) 1.0025(10) -0.02905(16) 0.0339(8) Uani 1 1 d . . . . .
C22B C -0.1592(3) 0.9320(12) 0.02917(16) 0.0417(9) Uani 1 1 d . . . . .
H22B H -0.0922 0.8501 0.0382 0.050 Uiso 1 1 calc R U . . .
N23B N -0.2192(3) 0.9755(10) 0.07244(14) 0.0451(8) Uani 1 1 d . . . . .
C24B C -0.3155(3) 1.0945(12) 0.05853(19) 0.0457(10) Uani 1 1 d . . . . .
H24B H -0.3580 1.1324 0.0883 0.055 Uiso 1 1 calc R U . . .
C25B C -0.3541(3) 1.1624(13) 0.0029(2) 0.0509(11) Uani 1 1 d . . . . .
H25B H -0.4221 1.2367 -0.0049 0.061 Uiso 1 1 calc R U . . .
C26B C -0.2913(3) 1.1200(11) -0.04188(17) 0.0426(9) Uani 1 1 d . . . . .
H26B H -0.3159 1.1697 -0.0800 0.051 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
Cl1A C14A 1.745(4) . ?
O1A C1A 1.204(4) . ?
O2A C1A 1.358(4) . ?
O2A C11A 1.402(4) . ?
C1A N1A 1.353(5) . ?
N1A C21A 1.399(5) . ?
N1A H1A 0.82(4) . ?
C11A C16A 1.367(5) . ?
C11A C12A 1.377(5) . ?
C12A C13A 1.383(6) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.375(6) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.375(6) . ?
C15A C16A 1.385(6) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C21A C26A 1.386(5) . ?
C21A C22A 1.395(5) . ?
C22A N23A 1.324(5) . ?
C22A H22A 0.9300 . ?
N23A C24A 1.325(5) . ?
C24A C25A 1.384(6) . ?
C24A H24A 0.9300 . ?
C25A C26A 1.375(6) . ?
C25A H25A 0.9300 . ?
C26A H26A 0.9300 . ?
Cl1B C14B 1.743(4) . ?
O1B C1B 1.209(4) . ?
O2B C1B 1.356(5) . ?
O2B C11B 1.402(4) . ?
C1B N1B 1.348(5) . ?
N1B C21B 1.396(5) . ?
N1B H1B 0.80(4) . ?
C11B C16B 1.366(5) . ?
C11B C12B 1.373(5) . ?
C12B C13B 1.384(6) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.372(6) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.374(6) . ?
C15B C16B 1.386(6) . ?
C15B H15B 0.9300 . ?
C16B H16B 0.9300 . ?
C21B C26B 1.381(5) . ?
C21B C22B 1.397(5) . ?
C22B N23B 1.330(5) . ?
C22B H22B 0.9300 . ?
N23B C24B 1.342(5) . ?
C24B C25B 1.362(6) . ?
C24B H24B 0.9300 . ?
C25B C26B 1.380(6) . ?
C25B H25B 0.9300 . ?
C26B H26B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A O2A C11A 118.0(3) . . ?
O1A C1A N1A 127.3(3) . . ?
O1A C1A O2A 124.1(3) . . ?
N1A C1A O2A 108.6(3) . . ?
C1A N1A C21A 125.7(3) . . ?
C1A N1A H1A 118(3) . . ?
C21A N1A H1A 116(3) . . ?
C16A C11A C12A 121.8(3) . . ?
C16A C11A O2A 117.1(3) . . ?
C12A C11A O2A 120.9(3) . . ?
C11A C12A C13A 119.0(4) . . ?
C11A C12A H12A 120.5 . . ?
C13A C12A H12A 120.5 . . ?
C14A C13A C12A 119.2(4) . . ?
C14A C13A H13A 120.4 . . ?
C12A C13A H13A 120.4 . . ?
C15A C14A C13A 121.7(4) . . ?
C15A C14A Cl1A 119.1(3) . . ?
C13A C14A Cl1A 119.2(3) . . ?
C14A C15A C16A 119.0(4) . . ?
C14A C15A H15A 120.5 . . ?
C16A C15A H15A 120.5 . . ?
C11A C16A C15A 119.4(4) . . ?
C11A C16A H16A 120.3 . . ?
C15A C16A H16A 120.3 . . ?
C26A C21A C22A 117.3(3) . . ?
C26A C21A N1A 118.0(3) . . ?
C22A C21A N1A 124.7(3) . . ?
N23A C22A C21A 123.3(3) . . ?
N23A C22A H22A 118.3 . . ?
C21A C22A H22A 118.3 . . ?
C22A N23A C24A 118.8(3) . . ?
N23A C24A C25A 122.0(4) . . ?
N23A C24A H24A 119.0 . . ?
C25A C24A H24A 119.0 . . ?
C26A C25A C24A 119.3(4) . . ?
C26A C25A H25A 120.3 . . ?
C24A C25A H25A 120.3 . . ?
C25A C26A C21A 119.2(4) . . ?
C25A C26A H26A 120.4 . . ?
C21A C26A H26A 120.4 . . ?
C1B O2B C11B 117.4(3) . . ?
O1B C1B N1B 126.3(3) . . ?
O1B C1B O2B 124.0(3) . . ?
N1B C1B O2B 109.7(3) . . ?
C1B N1B C21B 122.6(3) . . ?
C1B N1B H1B 116(3) . . ?
C21B N1B H1B 121(3) . . ?
C16B C11B C12B 121.4(4) . . ?
C16B C11B O2B 116.6(3) . . ?
C12B C11B O2B 121.8(3) . . ?
C11B C12B C13B 119.8(4) . . ?
C11B C12B H12B 120.1 . . ?
C13B C12B H12B 120.1 . . ?
C14B C13B C12B 118.8(4) . . ?
C14B C13B H13B 120.6 . . ?
C12B C13B H13B 120.6 . . ?
C13B C14B C15B 121.4(4) . . ?
C13B C14B Cl1B 119.6(3) . . ?
C15B C14B Cl1B 119.0(4) . . ?
C14B C15B C16B 119.6(4) . . ?
C14B C15B H15B 120.2 . . ?
C16B C15B H15B 120.2 . . ?
C11B C16B C15B 119.1(4) . . ?
C11B C16B H16B 120.5 . . ?
C15B C16B H16B 120.5 . . ?
C26B C21B N1B 120.6(3) . . ?
C26B C21B C22B 117.6(3) . . ?
N1B C21B C22B 121.8(3) . . ?
N23B C22B C21B 123.7(3) . . ?
N23B C22B H22B 118.2 . . ?
C21B C22B H22B 118.2 . . ?
C22B N23B C24B 117.2(3) . . ?
N23B C24B C25B 123.2(4) . . ?
N23B C24B H24B 118.4 . . ?
C25B C24B H24B 118.4 . . ?
C24B C25B C26B 119.4(4) . . ?
C24B C25B H25B 120.3 . . ?
C26B C25B H25B 120.3 . . ?
C25B C26B C21B 118.9(4) . . ?
C25B C26B H26B 120.5 . . ?
C21B C26B H26B 120.5 . . ?

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
C11A O2A C1A O1A -1.2(5) . . . . ?
C11A O2A C1A N1A 179.3(3) . . . . ?
O1A C1A N1A C21A 0.1(7) . . . . ?
O2A C1A N1A C21A 179.6(3) . . . . ?
C1A O2A C11A C16A 122.7(4) . . . . ?
C1A O2A C11A C12A -61.7(5) . . . . ?
C16A C11A C12A C13A -0.5(6) . . . . ?
O2A C11A C12A C13A -175.9(3) . . . . ?
C11A C12A C13A C14A 0.1(6) . . . . ?
C12A C13A C14A C15A 0.6(6) . . . . ?
C12A C13A C14A Cl1A 179.7(3) . . . . ?
C13A C14A C15A C16A -0.9(6) . . . . ?
Cl1A C14A C15A C16A 180.0(3) . . . . ?
C12A C11A C16A C15A 0.2(6) . . . . ?
O2A C11A C16A C15A 175.8(3) . . . . ?
C14A C15A C16A C11A 0.4(6) . . . . ?
C1A N1A C21A C26A -167.6(4) . . . . ?
C1A N1A C21A C22A 13.8(6) . . . . ?
C26A C21A C22A N23A -0.3(6) . . . . ?
N1A C21A C22A N23A 178.2(4) . . . . ?
C21A C22A N23A C24A 0.1(6) . . . . ?
C22A N23A C24A C25A -0.1(7) . . . . ?
N23A C24A C25A C26A 0.3(7) . . . . ?
C24A C25A C26A C21A -0.5(7) . . . . ?
C22A C21A C26A C25A 0.5(6) . . . . ?
N1A C21A C26A C25A -178.1(4) . . . . ?
C11B O2B C1B O1B 2.7(6) . . . . ?
C11B O2B C1B N1B 179.5(3) . . . . ?
O1B C1B N1B C21B -6.1(7) . . . . ?
O2B C1B N1B C21B 177.1(3) . . . . ?
C1B O2B C11B C16B -130.5(4) . . . . ?
C1B O2B C11B C12B 54.2(5) . . . . ?
C16B C11B C12B C13B 1.5(6) . . . . ?
O2B C11B C12B C13B 176.6(4) . . . . ?
C11B C12B C13B C14B -1.4(6) . . . . ?
C12B C13B C14B C15B 1.0(7) . . . . ?
C12B C13B C14B Cl1B 179.4(3) . . . . ?
C13B C14B C15B C16B -0.8(7) . . . . ?
Cl1B C14B C15B C16B -179.2(3) . . . . ?
C12B C11B C16B C15B -1.3(6) . . . . ?
O2B C11B C16B C15B -176.6(4) . . . . ?
C14B C15B C16B C11B 0.9(6) . . . . ?
C1B N1B C21B C26B 140.2(4) . . . . ?
C1B N1B C21B C22B -41.8(6) . . . . ?
C26B C21B C22B N23B -0.7(6) . . . . ?
N1B C21B C22B N23B -178.8(4) . . . . ?
C21B C22B N23B C24B -0.1(7) . . . . ?
C22B N23B C24B C25B 1.7(7) . . . . ?
N23B C24B C25B C26B -2.3(7) . . . . ?
C24B C25B C26B C21B 1.3(7) . . . . ?
N1B C21B C26B C25B 178.2(4) . . . . ?
C22B C21B C26B C25B 0.1(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
#   D    H    A     D-H       H...A     D...A     D-H...A   symm   publ
#   -    -    -     ---       -----     -----     -------   ----   ----
N1A H1A N23B 0.82(4) 2.16(4) 2.980(5) 176(4) . yes
N1B H1B N23A 0.80(4) 2.13(4) 2.929(5) 173(4) 2_564 yes
C16A H16A O1B 0.93 2.29 3.193(5) 163 1_545 yes
C16B H16B O1A 0.93 2.42 3.299(5) 157 2_574 yes
C22A H22A O1A 0.93 2.28 2.879(5) 122 . yes
C22B H22B O1B 0.93 2.54 2.929(5) 106 . yes
#   C22B H22B O2A   0.93      2.62      3.323(5)  133       .      yes



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone/chloroform'
_chemical_properties_physical    Moisture-sensitive
