# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1064026'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2015-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        5-phenyl-1H-pyrrole-2-carbaldehyde
_chemical_name_common            5-phenyl-2-formylpyrrole
_chemical_formula_moiety         'C11 H9 N O'
_chemical_formula_sum            'C11 H9 N O'
_chemical_melting_point          ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         171.19

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.328(5)
_cell_length_b                   5.042(2)
_cell_length_c                   15.578(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.947(11)
_cell_angle_gamma                90
_cell_volume                     836.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3646
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      32.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12299
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.782
_diffrn_reflns_theta_max         32.434
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2994
_reflns_number_gt                2356
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer

_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)+(0.0711P)²+0.1065P] 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         2994
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1279
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.51658(8) 0.19956(16) 0.59406(6) 0.02920(19) Uani 1 1 d . . . . .
N1 N 0.34284(8) -0.24258(16) 0.53249(5) 0.01780(17) Uani 1 1 d . . . . .
C2 C 0.36384(9) -0.09442(19) 0.61025(6) 0.01918(19) Uani 1 1 d . . . . .
C3 C 0.28508(10) -0.1887(2) 0.65434(7) 0.0235(2) Uani 1 1 d . . . . .
H3 H 0.2793 -0.1240 0.7101 0.028 Uiso 1 1 calc R U . . .
C4 C 0.21565(10) -0.3965(2) 0.60191(7) 0.0221(2) Uani 1 1 d . . . . .
H4 H 0.1540 -0.4992 0.6156 0.027 Uiso 1 1 calc R U . . .
C5 C 0.25278(9) -0.42659(18) 0.52606(6) 0.01776(18) Uani 1 1 d . . . . .
C6 C 0.45040(9) 0.1209(2) 0.63614(7) 0.0223(2) Uani 1 1 d . . . . .
H6 H 0.4571 0.2112 0.6911 0.027 Uiso 1 1 calc R U . . .
C7 C 0.20938(9) -0.61991(18) 0.45205(6) 0.01792(18) Uani 1 1 d . . . . .
C8 C 0.10407(10) -0.7749(2) 0.44328(7) 0.0226(2) Uani 1 1 d . . . . .
H8 H 0.0603 -0.7519 0.4851 0.027 Uiso 1 1 calc R U . . .
C9 C 0.06234(10) -0.9619(2) 0.37443(7) 0.0258(2) Uani 1 1 d . . . . .
H9 H -0.0097 -1.0658 0.3693 0.031 Uiso 1 1 calc R U . . .
C10 C 0.12482(11) -0.9982(2) 0.31326(7) 0.0256(2) Uani 1 1 d . . . . .
H10 H 0.0961 -1.1264 0.2660 0.031 Uiso 1 1 calc R U . . .
C11 C 0.22963(11) -0.8462(2) 0.32153(7) 0.0252(2) Uani 1 1 d . . . . .
H11 H 0.2731 -0.8706 0.2796 0.030 Uiso 1 1 calc R U . . .
C12 C 0.27217(10) -0.6583(2) 0.39029(7) 0.0226(2) Uani 1 1 d . . . . .
H12 H 0.3445 -0.5554 0.3952 0.027 Uiso 1 1 calc R U . . .
H1 H 0.3859(14) -0.209(3) 0.4921(10) 0.032(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.2182(13) . ?
N1 C5 1.3571(13) . ?
N1 C2 1.3731(13) . ?
N1 H1 0.933(15) . ?
C2 C3 1.3827(14) . ?
C2 C6 1.4259(15) . ?
C3 C4 1.3945(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3911(14) . ?
C4 H4 0.9500 . ?
C5 C7 1.4609(14) . ?
C6 H6 0.9500 . ?
C7 C12 1.3914(14) . ?
C7 C8 1.3931(14) . ?
C8 C9 1.3846(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.3794(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.3817(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3874(14) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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
C5 N1 C2 109.67(8) . . ?
C5 N1 H1 128.7(9) . . ?
C2 N1 H1 121.6(9) . . ?
N1 C2 C3 107.71(9) . . ?
N1 C2 C6 124.00(9) . . ?
C3 C2 C6 128.27(9) . . ?
C2 C3 C4 107.33(9) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
C5 C4 C3 107.81(9) . . ?
C5 C4 H4 126.1 . . ?
C3 C4 H4 126.1 . . ?
N1 C5 C4 107.47(8) . . ?
N1 C5 C7 123.81(8) . . ?
C4 C5 C7 128.70(9) . . ?
O1 C6 C2 125.84(10) . . ?
O1 C6 H6 117.1 . . ?
C2 C6 H6 117.1 . . ?
C12 C7 C8 118.48(9) . . ?
C12 C7 C5 121.65(9) . . ?
C8 C7 C5 119.86(9) . . ?
C9 C8 C7 120.83(10) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 120.37(10) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.27(10) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 120.79(10) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C7 120.26(10) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 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
C5 N1 C2 C3 0.29(11) . . . . ?
C5 N1 C2 C6 -178.21(9) . . . . ?
N1 C2 C3 C4 -0.12(11) . . . . ?
C6 C2 C3 C4 178.29(10) . . . . ?
C2 C3 C4 C5 -0.08(12) . . . . ?
C2 N1 C5 C4 -0.33(11) . . . . ?
C2 N1 C5 C7 -178.95(8) . . . . ?
C3 C4 C5 N1 0.25(11) . . . . ?
C3 C4 C5 C7 178.79(9) . . . . ?
N1 C2 C6 O1 -0.55(17) . . . . ?
C3 C2 C6 O1 -178.73(11) . . . . ?
N1 C5 C7 C12 10.88(14) . . . . ?
C4 C5 C7 C12 -167.43(10) . . . . ?
N1 C5 C7 C8 -170.41(9) . . . . ?
C4 C5 C7 C8 11.27(15) . . . . ?
C12 C7 C8 C9 -0.33(15) . . . . ?
C5 C7 C8 C9 -179.08(9) . . . . ?
C7 C8 C9 C10 0.12(16) . . . . ?
C8 C9 C10 C11 0.09(16) . . . . ?
C9 C10 C11 C12 -0.09(16) . . . . ?
C10 C11 C12 C7 -0.13(16) . . . . ?
C8 C7 C12 C11 0.34(15) . . . . ?
C5 C7 C12 C11 179.06(9) . . . . ?

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-3

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Diethyl ether'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1064027'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2015-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
5-(3,5-dimethylphenyl)-1H-pyrrole-2-carbaldehyde
_chemical_name_common            5-(3,5-dimethylphenyl)-2-formylpyrrole
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_melting_point          ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         199.24

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'

_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                   8.0139(18)
_cell_length_b                   13.509(2)
_cell_length_c                   10.342(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.552(9)
_cell_angle_gamma                90
_cell_volume                     1092.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1206
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      21.78
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   'SADABS (Sheldrick ,1996)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7793
_diffrn_reflns_av_unetI/netI     0.1395
_diffrn_reflns_av_R_equivalents  0.1412
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.016
_diffrn_reflns_theta_max         26.389
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2202
_reflns_number_gt                1060
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer

_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)+(0.1849P)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         2202
_refine_ls_number_parameters     142
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1782
_refine_ls_R_factor_gt           0.1218
_refine_ls_wR_factor_ref         0.2996
_refine_ls_wR_factor_gt          0.2843
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_restrained_S_all      0.896
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0441(5) 0.6004(2) 0.0975(4) 0.0760(12) Uani 1 1 d . . . . .
N1 N 0.7617(4) 0.4657(2) 0.1006(3) 0.0385(9) Uani 1 1 d D . . . .
C2 C 0.7969(5) 0.5541(3) 0.1691(4) 0.0395(10) Uani 1 1 d . . . . .
C3 C 0.6725(6) 0.5684(3) 0.2372(4) 0.0468(11) Uani 1 1 d . . . . .
H3 H 0.6642 0.6232 0.2931 0.056 Uiso 1 1 calc R U . . .
C4 C 0.5580(6) 0.4887(3) 0.2114(4) 0.0473(11) Uani 1 1 d . . . . .
H4 H 0.4585 0.4796 0.2461 0.057 Uiso 1 1 calc R U . . .
C5 C 0.6178(5) 0.4255(3) 0.1255(4) 0.0345(10) Uani 1 1 d . . . . .
C6 C 0.9358(6) 0.6168(3) 0.1611(5) 0.0525(12) Uani 1 1 d . . . . .
H6 H 0.9454 0.6770 0.2097 0.063 Uiso 1 1 calc R U . . .
C7 C 0.5463(5) 0.3309(3) 0.0694(4) 0.0355(10) Uani 1 1 d . . . . .
C8 C 0.3872(5) 0.3004(3) 0.0889(5) 0.0462(11) Uani 1 1 d . . . . .
H8 H 0.3262 0.3421 0.1364 0.055 Uiso 1 1 calc R U . . .
C9 C 0.3149(6) 0.2092(3) 0.0397(5) 0.0538(13) Uani 1 1 d . . . . .
C10 C 0.4070(6) 0.1527(3) -0.0350(5) 0.0522(12) Uani 1 1 d . . . . .
H10 H 0.3591 0.0921 -0.0723 0.063 Uiso 1 1 calc R U . . .
C11 C 0.5595(6) 0.1803(3) -0.0562(4) 0.0481(12) Uani 1 1 d . . . . .
C12 C 0.6322(5) 0.2707(3) -0.0032(4) 0.0416(11) Uani 1 1 d . . . . .
H12 H 0.7406 0.2904 -0.0173 0.050 Uiso 1 1 calc R U . . .
C13 C 0.1475(7) 0.1767(4) 0.0656(7) 0.0843(19) Uani 1 1 d . . . . .
H13A H 0.0932 0.1300 -0.0034 0.126 Uiso 1 1 calc R U . . .
H13B H 0.0732 0.2344 0.0648 0.126 Uiso 1 1 calc R U . . .
H13C H 0.1659 0.1443 0.1523 0.126 Uiso 1 1 calc R U . . .
C14 C 0.6551(7) 0.1151(4) -0.1324(6) 0.0745(17) Uani 1 1 d . . . . .
H14A H 0.6924 0.0550 -0.0812 0.112 Uiso 1 1 calc R U . . .
H14B H 0.7552 0.1507 -0.1487 0.112 Uiso 1 1 calc R U . . .
H14C H 0.5802 0.0971 -0.2172 0.112 Uiso 1 1 calc R U . . .
H1 H 0.829(5) 0.441(3) 0.048(4) 0.049(12) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.219(6) . ?
N1 C5 1.349(5) . ?
N1 C2 1.386(5) . ?
N1 H1 0.914(19) . ?
C2 C3 1.354(6) . ?
C2 C6 1.415(6) . ?
C3 C4 1.402(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(6) . ?
C4 H4 0.9500 . ?
C5 C7 1.467(5) . ?
C6 H6 0.9500 . ?
C7 C12 1.387(5) . ?
C7 C8 1.396(6) . ?
C8 C9 1.408(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.405(7) . ?
C9 C13 1.490(7) . ?
C10 C11 1.340(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.411(6) . ?
C11 C14 1.499(7) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C2 109.7(3) . . ?
C5 N1 H1 127(3) . . ?
C2 N1 H1 123(3) . . ?
C3 C2 N1 107.3(3) . . ?
C3 C2 C6 128.5(4) . . ?
N1 C2 C6 124.2(4) . . ?
C2 C3 C4 108.5(4) . . ?
C2 C3 H3 125.7 . . ?
C4 C3 H3 125.7 . . ?
C5 C4 C3 106.9(4) . . ?
C5 C4 H4 126.6 . . ?
C3 C4 H4 126.6 . . ?
N1 C5 C4 107.6(3) . . ?
N1 C5 C7 123.5(4) . . ?
C4 C5 C7 128.9(4) . . ?
O1 C6 C2 125.8(4) . . ?
O1 C6 H6 117.1 . . ?
C2 C6 H6 117.1 . . ?
C12 C7 C8 118.8(4) . . ?
C12 C7 C5 121.8(3) . . ?
C8 C7 C5 119.4(4) . . ?
C7 C8 C9 121.6(4) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C8 116.7(4) . . ?
C10 C9 C13 122.7(4) . . ?
C8 C9 C13 120.6(5) . . ?
C11 C10 C9 123.0(4) . . ?
C11 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
C10 C11 C12 119.5(4) . . ?
C10 C11 C14 120.7(4) . . ?
C12 C11 C14 119.8(4) . . ?
C7 C12 C11 120.4(4) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 0.1(4) . . . . ?
C5 N1 C2 C6 -177.7(4) . . . . ?
N1 C2 C3 C4 -0.1(5) . . . . ?
C6 C2 C3 C4 177.5(4) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C2 N1 C5 C4 0.0(4) . . . . ?
C2 N1 C5 C7 -179.3(3) . . . . ?
C3 C4 C5 N1 -0.1(4) . . . . ?
C3 C4 C5 C7 179.1(4) . . . . ?
C3 C2 C6 O1 -179.7(5) . . . . ?
N1 C2 C6 O1 -2.4(7) . . . . ?
N1 C5 C7 C12 6.8(6) . . . . ?
C4 C5 C7 C12 -172.4(4) . . . . ?
N1 C5 C7 C8 -173.0(4) . . . . ?
C4 C5 C7 C8 7.8(6) . . . . ?
C12 C7 C8 C9 1.7(6) . . . . ?
C5 C7 C8 C9 -178.5(4) . . . . ?
C7 C8 C9 C10 -2.8(6) . . . . ?
C7 C8 C9 C13 178.0(4) . . . . ?
C8 C9 C10 C11 2.4(7) . . . . ?
C13 C9 C10 C11 -178.4(5) . . . . ?
C9 C10 C11 C12 -0.8(7) . . . . ?
C9 C10 C11 C14 177.7(5) . . . . ?
C8 C7 C12 C11 0.1(6) . . . . ?
C5 C7 C12 C11 -179.8(4) . . . . ?
C10 C11 C12 C7 -0.5(6) . . . . ?
C14 C11 C12 C7 -179.0(4) . . . . ?

_refine_diff_density_max         0.437
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.115

_shelxl_version_number           2014-3

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1064028'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2015-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
5-(3,5-bis(trifluoromethyl)phenyl)-1H-pyrrole-2-carbaldehyde
_chemical_name_common            
5-(3,5-bis(trifluoromethyl)phenyl)-2-formylpyrrole
_chemical_formula_moiety         'C13 H7 F6 N O'
_chemical_formula_sum            'C13 H7 F6 N O'
_chemical_melting_point          ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         307.20

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.086(2)
_cell_length_b                   4.7468(7)
_cell_length_c                   19.887(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.901(9)
_cell_angle_gamma                90
_cell_volume                     1188.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1331
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      23.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.173
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10048
_diffrn_reflns_av_unetI/netI     0.0762
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.008
_diffrn_reflns_theta_max         25.788
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2257
_reflns_number_gt                1381
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer

_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)+(0.0418P)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         2257
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0863
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.948
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.01151(13) 0.1918(3) 0.41752(9) 0.0480(5) Uani 1 1 d . . . . .
F2 F -0.07199(11) -0.0749(3) 0.32911(10) 0.0481(5) Uani 1 1 d . . . . .
F3 F -0.00052(13) 0.3205(3) 0.31725(9) 0.0463(5) Uani 1 1 d . . . . .
F4 F 0.35399(12) 0.1447(3) 0.27819(8) 0.0360(4) Uani 1 1 d . . . . .
F5 F 0.27869(13) -0.2193(3) 0.22344(8) 0.0419(4) Uani 1 1 d . . . . .
F6 F 0.42413(12) -0.2628(3) 0.30417(8) 0.0352(4) Uani 1 1 d . . . . .
O1 O 0.49901(14) -1.2055(3) 0.56782(10) 0.0288(5) Uani 1 1 d . . . . .
N1 N 0.34886(16) -0.7618(4) 0.51077(11) 0.0190(5) Uani 1 1 d . . . . .
C2 C 0.35331(19) -0.9170(5) 0.56918(13) 0.0194(6) Uani 1 1 d . . . . .
C3 C 0.2715(2) -0.8271(5) 0.59559(14) 0.0259(6) Uani 1 1 d . . . . .
H3 H 0.2553 -0.8972 0.6362 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2176(2) -0.6169(5) 0.55216(14) 0.0261(6) Uani 1 1 d . . . . .
H4 H 0.1577 -0.5163 0.5577 0.031 Uiso 1 1 calc R U . . .
C5 C 0.26632(18) -0.5785(5) 0.49911(13) 0.0199(6) Uani 1 1 d . . . . .
C6 C 0.42957(19) -1.1347(5) 0.59459(14) 0.0237(6) Uani 1 1 d . . . . .
H6 H 0.4259 -1.2319 0.6356 0.028 Uiso 1 1 calc R U . . .
C7 C 0.23826(18) -0.3825(5) 0.44040(13) 0.0195(6) Uani 1 1 d . . . . .
C8 C 0.14392(19) -0.2281(5) 0.42877(14) 0.0218(6) Uani 1 1 d . . . . .
H8 H 0.1007 -0.2487 0.4599 0.026 Uiso 1 1 calc R U . . .
C9 C 0.11277(19) -0.0459(5) 0.37257(14) 0.0218(6) Uani 1 1 d . . . . .
C10 C 0.17464(19) -0.0100(5) 0.32682(13) 0.0214(6) Uani 1 1 d . . . . .
H10 H 0.1533 0.1157 0.2883 0.026 Uiso 1 1 calc R U . . .
C11 C 0.26851(19) -0.1618(5) 0.33849(13) 0.0198(6) Uani 1 1 d . . . . .
C12 C 0.30017(19) -0.3458(5) 0.39391(13) 0.0201(6) Uani 1 1 d . . . . .
H12 H 0.3645 -0.4483 0.4006 0.024 Uiso 1 1 calc R U . . .
C13 C 0.0081(2) 0.0987(5) 0.35927(15) 0.0290(7) Uani 1 1 d . . . . .
C14 C 0.3318(2) -0.1274(5) 0.28697(14) 0.0244(6) Uani 1 1 d . . . . .
H1 H 0.393(2) -0.777(5) 0.4868(14) 0.029(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.329(3) . ?
F2 C13 1.339(3) . ?
F3 C13 1.330(3) . ?
F4 C14 1.346(3) . ?
F5 C14 1.337(3) . ?
F6 C14 1.328(3) . ?
O1 C6 1.220(3) . ?
N1 C5 1.356(3) . ?
N1 C2 1.363(3) . ?
N1 H1 0.85(3) . ?
C2 C3 1.383(3) . ?
C2 C6 1.429(3) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C7 1.459(3) . ?
C6 H6 0.9500 . ?
C7 C12 1.397(3) . ?
C7 C8 1.399(3) . ?
C8 C9 1.383(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 C13 1.489(3) . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(3) . ?
C11 C14 1.492(3) . ?
C12 H12 0.9500 . ?

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
C5 N1 C2 109.8(2) . . ?
C5 N1 H1 126.4(17) . . ?
C2 N1 H1 123.8(17) . . ?
N1 C2 C3 107.5(2) . . ?
N1 C2 C6 123.7(2) . . ?
C3 C2 C6 128.8(2) . . ?
C4 C3 C2 107.5(2) . . ?
C4 C3 H3 126.2 . . ?
C2 C3 H3 126.2 . . ?
C3 C4 C5 108.0(2) . . ?
C3 C4 H4 126.0 . . ?
C5 C4 H4 126.0 . . ?
N1 C5 C4 107.2(2) . . ?
N1 C5 C7 124.0(2) . . ?
C4 C5 C7 128.7(2) . . ?
O1 C6 C2 125.2(2) . . ?
O1 C6 H6 117.4 . . ?
C2 C6 H6 117.4 . . ?
C12 C7 C8 118.1(2) . . ?
C12 C7 C5 123.0(2) . . ?
C8 C7 C5 118.9(2) . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.8(2) . . ?
C8 C9 C13 119.0(2) . . ?
C10 C9 C13 120.1(2) . . ?
C9 C10 C11 118.5(2) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C12 C11 C10 121.4(2) . . ?
C12 C11 C14 121.1(2) . . ?
C10 C11 C14 117.4(2) . . ?
C11 C12 C7 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
F1 C13 F3 106.3(2) . . ?
F1 C13 F2 106.3(2) . . ?
F3 C13 F2 106.5(2) . . ?
F1 C13 C9 112.7(2) . . ?
F3 C13 C9 113.1(2) . . ?
F2 C13 C9 111.4(2) . . ?
F6 C14 F5 106.6(2) . . ?
F6 C14 F4 106.52(19) . . ?
F5 C14 F4 105.4(2) . . ?
F6 C14 C11 114.0(2) . . ?
F5 C14 C11 111.7(2) . . ?
F4 C14 C11 112.0(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
C5 N1 C2 C3 -0.6(3) . . . . ?
C5 N1 C2 C6 178.2(2) . . . . ?
N1 C2 C3 C4 0.3(3) . . . . ?
C6 C2 C3 C4 -178.4(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C2 N1 C5 C4 0.6(3) . . . . ?
C2 N1 C5 C7 -179.4(2) . . . . ?
C3 C4 C5 N1 -0.4(3) . . . . ?
C3 C4 C5 C7 179.5(2) . . . . ?
N1 C2 C6 O1 0.4(4) . . . . ?
C3 C2 C6 O1 178.9(3) . . . . ?
N1 C5 C7 C12 -6.3(4) . . . . ?
C4 C5 C7 C12 173.7(2) . . . . ?
N1 C5 C7 C8 172.2(2) . . . . ?
C4 C5 C7 C8 -7.8(4) . . . . ?
C12 C7 C8 C9 0.4(3) . . . . ?
C5 C7 C8 C9 -178.2(2) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C7 C8 C9 C13 175.7(2) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C13 C9 C10 C11 -176.0(2) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C9 C10 C11 C14 177.8(2) . . . . ?
C10 C11 C12 C7 -0.5(3) . . . . ?
C14 C11 C12 C7 -177.9(2) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
C5 C7 C12 C11 178.6(2) . . . . ?
C8 C9 C13 F1 42.0(3) . . . . ?
C10 C9 C13 F1 -141.7(2) . . . . ?
C8 C9 C13 F3 162.7(2) . . . . ?
C10 C9 C13 F3 -21.0(3) . . . . ?
C8 C9 C13 F2 -77.3(3) . . . . ?
C10 C9 C13 F2 99.0(3) . . . . ?
C12 C11 C14 F6 -7.1(3) . . . . ?
C10 C11 C14 F6 175.4(2) . . . . ?
C12 C11 C14 F5 113.9(3) . . . . ?
C10 C11 C14 F5 -63.6(3) . . . . ?
C12 C11 C14 F4 -128.1(2) . . . . ?
C10 C11 C14 F4 54.3(3) . . . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.055

_shelxl_version_number           2014-3

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Diethyl ether'
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1064029'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2015-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
5-(2,4,6-triisopropylphenyl)-1H-pyrrole-2-carbaldehyde
_chemical_name_common            5-(2,4,6-triisopropylphenyl)-2-formylpyrrole
_chemical_formula_moiety         'C19.43 H25.30 N O, 0.566(C H3)'
_chemical_formula_sum            'C20 H27 N O'
_chemical_melting_point          ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         297.43

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'

_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                   8.6799(13)
_cell_length_b                   9.8371(13)
_cell_length_c                   12.608(2)
_cell_angle_alpha                72.477(7)
_cell_angle_beta                 70.308(5)
_cell_angle_gamma                65.232(4)
_cell_volume                     904.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1310
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      24.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.093
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7972
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.321
_diffrn_reflns_theta_max         25.741
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3402
_reflns_number_gt                1968
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer

_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)+(0.0527P)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         3402
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1169
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      0.942
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.72516(17) -0.10252(17) 1.02520(12) 0.0620(5) Uani 1 1 d . . . . .
N1 N 0.58267(18) 0.17372(16) 0.86569(12) 0.0321(4) Uani 1 1 d . . . . .
C2 C 0.7534(2) 0.1049(2) 0.87587(14) 0.0330(4) Uani 1 1 d . . . . .
C3 C 0.8451(2) 0.1921(2) 0.79681(15) 0.0439(5) Uani 1 1 d . . . . .
H3 H 0.9661 0.1728 0.7839 0.053 Uiso 1 1 calc R U . . .
C4 C 0.7292(2) 0.3139(2) 0.73881(15) 0.0461(5) Uani 1 1 d . . . . .
H4 H 0.7569 0.3927 0.6796 0.055 Uiso 1 1 calc R U . . .
C5 C 0.5674(2) 0.29952(19) 0.78265(13) 0.0323(4) Uani 1 1 d . . . . .
C6 C 0.8129(2) -0.0291(2) 0.95599(16) 0.0439(5) Uani 1 1 d . . . . .
H6 H 0.9331 -0.0658 0.9560 0.053 Uiso 1 1 calc R U . . .
C7 C 0.3978(2) 0.39972(19) 0.75219(13) 0.0330(4) Uani 1 1 d . . . . .
C8 C 0.3491(2) 0.3664(2) 0.66976(15) 0.0395(5) Uani 1 1 d . . . . .
C9 C 0.1943(3) 0.4660(2) 0.63931(17) 0.0531(6) Uani 1 1 d . . . . .
H9 H 0.1602 0.4448 0.5837 0.064 Uiso 1 1 calc R U . . .
C10 C 0.0875(3) 0.5949(2) 0.68658(18) 0.0554(6) Uani 1 1 d . . . . .
C11 C 0.1379(2) 0.6229(2) 0.76865(16) 0.0461(5) Uani 1 1 d . . . . .
H11 H 0.0658 0.7103 0.8024 0.055 Uiso 1 1 calc R U . . .
C12 C 0.2911(2) 0.5269(2) 0.80346(14) 0.0354(4) Uani 1 1 d . . . . .
C13 C 0.4594(3) 0.2279(2) 0.61457(15) 0.0423(5) Uani 1 1 d . . . . .
H13 H 0.5688 0.1771 0.6427 0.051 Uiso 1 1 calc R U . . .
C15 C 0.3350(2) 0.5626(2) 0.89607(14) 0.0391(5) Uani 1 1 d . . . . .
H15 H 0.4493 0.4831 0.9083 0.047 Uiso 1 1 calc R U . . .
C16 C 0.5135(3) 0.2699(2) 0.48400(16) 0.0608(6) Uani 1 1 d . . . . .
H16A H 0.4095 0.3144 0.4532 0.091 Uiso 1 1 calc R U . . .
H16B H 0.5940 0.1781 0.4526 0.091 Uiso 1 1 calc R U . . .
H16C H 0.5719 0.3441 0.4624 0.091 Uiso 1 1 calc R U . . .
C17 C 0.3657(3) 0.1144(2) 0.65235(17) 0.0573(6) Uani 1 1 d . . . . .
H17A H 0.3376 0.0861 0.7362 0.086 Uiso 1 1 calc R U . . .
H17B H 0.4416 0.0232 0.6191 0.086 Uiso 1 1 calc R U . . .
H17C H 0.2574 0.1609 0.6261 0.086 Uiso 1 1 calc R U . . .
C20 C 0.3578(3) 0.7160(2) 0.86071(16) 0.0548(6) Uani 1 1 d . . . . .
H20A H 0.4505 0.7171 0.7900 0.082 Uiso 1 1 calc R U . . .
H20B H 0.3896 0.7335 0.9217 0.082 Uiso 1 1 calc R U . . .
H20C H 0.2478 0.7967 0.8475 0.082 Uiso 1 1 calc R U . . .
C21 C 0.1984(3) 0.5522(3) 1.00888(16) 0.0611(6) Uani 1 1 d . . . . .
H21A H 0.0844 0.6286 0.9996 0.092 Uiso 1 1 calc R U . . .
H21B H 0.2318 0.5712 1.0685 0.092 Uiso 1 1 calc R U . . .
H21C H 0.1912 0.4503 1.0312 0.092 Uiso 1 1 calc R U . . .
C14A C -0.0567(11) 0.7127(9) 0.6249(7) 0.0462(17) Uani 0.566(9) 1 d . . P A 1
H14A H -0.0644 0.6604 0.5710 0.055 Uiso 0.566(9) 1 calc R U P A 1
C18A C -0.2195(11) 0.7359(14) 0.7142(8) 0.071(3) Uani 0.434(9) 1 d . . P A 1
H18A H -0.3173 0.8090 0.6809 0.107 Uiso 0.434(9) 1 calc R U P A 1
H18B H -0.2124 0.7757 0.7742 0.107 Uiso 0.434(9) 1 calc R U P A 1
H18C H -0.2382 0.6386 0.7474 0.107 Uiso 0.434(9) 1 calc R U P A 1
C19A C -0.0208(7) 0.8526(8) 0.5540(5) 0.076(2) Uani 0.566(9) 1 d . . P A 1
H19A H -0.0013 0.9029 0.6020 0.115 Uiso 0.566(9) 1 calc R U P A 1
H19B H -0.1211 0.9222 0.5221 0.115 Uiso 0.566(9) 1 calc R U P A 1
H19C H 0.0837 0.8245 0.4914 0.115 Uiso 0.566(9) 1 calc R U P A 1
C14B C -0.1013(13) 0.6942(12) 0.6718(8) 0.0355(19) Uani 0.434(9) 1 d . . P A 2
H14B H -0.1656 0.6251 0.6829 0.043 Uiso 0.434(9) 1 calc R U P A 2
C18B C -0.2148(7) 0.8160(8) 0.7377(5) 0.0643(17) Uani 0.566(9) 1 d . . P A 2
H18D H -0.2374 0.7719 0.8197 0.096 Uiso 0.566(9) 1 calc R U P A 2
H18E H -0.3258 0.8684 0.7147 0.096 Uiso 0.566(9) 1 calc R U P A 2
H18F H -0.1569 0.8890 0.7227 0.096 Uiso 0.566(9) 1 calc R U P A 2
C19B C -0.0582(8) 0.7655(11) 0.5424(6) 0.064(3) Uani 0.434(9) 1 d . . P A 2
H19D H -0.0036 0.6848 0.4968 0.095 Uiso 0.434(9) 1 calc R U P A 2
H19E H 0.0225 0.8186 0.5281 0.095 Uiso 0.434(9) 1 calc R U P A 2
H19F H -0.1663 0.8382 0.5205 0.095 Uiso 0.434(9) 1 calc R U P A 2
H1 H 0.494(2) 0.139(2) 0.9094(14) 0.041(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.223(2) . ?
N1 C5 1.349(2) . ?
N1 C2 1.381(2) . ?
N1 H1 0.917(18) . ?
C2 C3 1.373(2) . ?
C2 C6 1.416(3) . ?
C3 C4 1.393(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(2) . ?
C4 H4 0.9500 . ?
C5 C7 1.491(2) . ?
C6 H6 0.9500 . ?
C7 C12 1.397(2) . ?
C7 C8 1.408(2) . ?
C8 C9 1.389(2) . ?
C8 C13 1.512(3) . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(3) . ?
C10 C14A 1.553(7) . ?
C10 C14B 1.558(10) . ?
C11 C12 1.395(2) . ?
C11 H11 0.9500 . ?
C12 C15 1.514(2) . ?
C13 C17 1.522(3) . ?
C13 C16 1.527(2) . ?
C13 H13 1.0000 . ?
C15 C20 1.517(3) . ?
C15 C21 1.522(3) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C14A C18A 1.459(11) . ?
C14A C19A 1.490(8) . ?
C14A H14A 1.0000 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
C14B C18B 1.468(13) . ?
C14B C19B 1.554(8) . ?
C14B H14B 1.0000 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C2 109.75(15) . . ?
C5 N1 H1 125.6(11) . . ?
C2 N1 H1 124.6(11) . . ?
C3 C2 N1 106.89(15) . . ?
C3 C2 C6 129.14(16) . . ?
N1 C2 C6 123.96(16) . . ?
C2 C3 C4 107.88(16) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
C5 C4 C3 107.72(16) . . ?
C5 C4 H4 126.1 . . ?
C3 C4 H4 126.1 . . ?
N1 C5 C4 107.75(14) . . ?
N1 C5 C7 122.51(15) . . ?
C4 C5 C7 129.72(15) . . ?
O1 C6 C2 126.54(17) . . ?
O1 C6 H6 116.7 . . ?
C2 C6 H6 116.7 . . ?
C12 C7 C8 120.81(15) . . ?
C12 C7 C5 119.94(15) . . ?
C8 C7 C5 119.24(16) . . ?
C9 C8 C7 117.82(17) . . ?
C9 C8 C13 120.02(15) . . ?
C7 C8 C13 122.16(15) . . ?
C10 C9 C8 122.86(17) . . ?
C10 C9 H9 118.6 . . ?
C8 C9 H9 118.6 . . ?
C11 C10 C9 117.79(17) . . ?
C11 C10 C14A 124.6(4) . . ?
C9 C10 C14A 116.3(4) . . ?
C11 C10 C14B 116.4(4) . . ?
C9 C10 C14B 124.8(4) . . ?
C10 C11 C12 122.15(19) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C11 C12 C7 118.54(16) . . ?
C11 C12 C15 119.09(17) . . ?
C7 C12 C15 122.37(14) . . ?
C8 C13 C17 110.62(16) . . ?
C8 C13 C16 112.35(16) . . ?
C17 C13 C16 111.42(16) . . ?
C8 C13 H13 107.4 . . ?
C17 C13 H13 107.4 . . ?
C16 C13 H13 107.4 . . ?
C12 C15 C20 111.98(14) . . ?
C12 C15 C21 110.66(16) . . ?
C20 C15 C21 111.54(17) . . ?
C12 C15 H15 107.5 . . ?
C20 C15 H15 107.5 . . ?
C21 C15 H15 107.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C21 H21A 109.5 . . ?
C15 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C15 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18A C14A C19A 116.5(8) . . ?
C18A C14A C10 105.0(5) . . ?
C19A C14A C10 115.3(5) . . ?
C18A C14A H14A 106.5 . . ?
C19A C14A H14A 106.5 . . ?
C10 C14A H14A 106.5 . . ?
C14A C18A H18A 109.5 . . ?
C14A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C14A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C14A C19A H19A 109.5 . . ?
C14A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C14A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C18B C14B C19B 109.3(7) . . ?
C18B C14B C10 121.2(7) . . ?
C19B C14B C10 99.7(6) . . ?
C18B C14B H14B 108.7 . . ?
C19B C14B H14B 108.7 . . ?
C10 C14B H14B 108.7 . . ?
C14B C18B H18D 109.5 . . ?
C14B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C14B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C14B C19B H19D 109.5 . . ?
C14B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C14B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 0.3(2) . . . . ?
C5 N1 C2 C6 179.49(17) . . . . ?
N1 C2 C3 C4 0.0(2) . . . . ?
C6 C2 C3 C4 -179.11(19) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C2 N1 C5 C4 -0.5(2) . . . . ?
C2 N1 C5 C7 -179.27(15) . . . . ?
C3 C4 C5 N1 0.5(2) . . . . ?
C3 C4 C5 C7 179.15(17) . . . . ?
C3 C2 C6 O1 179.7(2) . . . . ?
N1 C2 C6 O1 0.7(3) . . . . ?
N1 C5 C7 C12 93.4(2) . . . . ?
C4 C5 C7 C12 -85.0(2) . . . . ?
N1 C5 C7 C8 -88.0(2) . . . . ?
C4 C5 C7 C8 93.6(2) . . . . ?
C12 C7 C8 C9 1.6(3) . . . . ?
C5 C7 C8 C9 -177.01(16) . . . . ?
C12 C7 C8 C13 -178.63(16) . . . . ?
C5 C7 C8 C13 2.8(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C13 C8 C9 C10 -179.9(2) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C8 C9 C10 C14A 166.6(4) . . . . ?
C8 C9 C10 C14B -168.9(4) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C14A C10 C11 C12 -165.9(4) . . . . ?
C14B C10 C11 C12 169.5(4) . . . . ?
C10 C11 C12 C7 1.0(3) . . . . ?
C10 C11 C12 C15 -178.31(18) . . . . ?
C8 C7 C12 C11 -2.0(3) . . . . ?
C5 C7 C12 C11 176.61(15) . . . . ?
C8 C7 C12 C15 177.27(16) . . . . ?
C5 C7 C12 C15 -4.2(3) . . . . ?
C9 C8 C13 C17 -68.0(2) . . . . ?
C7 C8 C13 C17 112.21(19) . . . . ?
C9 C8 C13 C16 57.2(2) . . . . ?
C7 C8 C13 C16 -122.58(19) . . . . ?
C11 C12 C15 C20 -61.2(2) . . . . ?
C7 C12 C15 C20 119.53(19) . . . . ?
C11 C12 C15 C21 63.9(2) . . . . ?
C7 C12 C15 C21 -115.3(2) . . . . ?
C11 C10 C14A C18A -67.2(8) . . . . ?
C9 C10 C14A C18A 126.3(7) . . . . ?
C14B C10 C14A C18A 8.5(13) . . . . ?
C11 C10 C14A C19A 62.4(9) . . . . ?
C9 C10 C14A C19A -104.2(7) . . . . ?
C14B C10 C14A C19A 138(2) . . . . ?
C11 C10 C14B C18B 3.1(8) . . . . ?
C9 C10 C14B C18B 171.3(5) . . . . ?
C14A C10 C14B C18B -114(2) . . . . ?
C11 C10 C14B C19B 122.7(7) . . . . ?
C9 C10 C14B C19B -69.1(7) . . . . ?
C14A C10 C14B C19B 5.7(12) . . . . ?

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.033

_shelxl_version_number           2014-3

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane'
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1064030'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2015-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
5-(2,6-dimethylphenyl)-1H-pyrrole-2-carbaldehyde
_chemical_name_common            5-(2,6-dimethylphenyl)-2-formylpyrrole
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_melting_point          ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Orange

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         199.24

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   7.9115(7)
_cell_length_b                   23.9817(18)
_cell_length_c                   11.4591(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.844(3)
_cell_angle_gamma                90
_cell_volume                     2158.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1075
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      22.61
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10811
_diffrn_reflns_av_unetI/netI     0.1067
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.114
_diffrn_reflns_theta_max         25.755
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4112
_reflns_number_gt                2320
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0364P)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         4112
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.0941
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_restrained_S_all      0.913
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.1106(2) 0.09342(7) -0.11068(15) 0.0343(4) Uani 1 1 d . . . . .
N1A N 0.4157(2) 0.09977(8) 0.06343(16) 0.0201(4) Uani 1 1 d . . . . .
C2A C 0.3630(3) 0.13759(9) -0.0240(2) 0.0210(5) Uani 1 1 d . . . . .
C3A C 0.4822(3) 0.17971(9) -0.0177(2) 0.0247(6) Uani 1 1 d . . . . .
H3A H 0.4788 0.2116 -0.0672 0.030 Uiso 1 1 calc R U . . .
C4A C 0.6092(3) 0.16720(9) 0.0744(2) 0.0263(6) Uani 1 1 d . . . . .
H4A H 0.7075 0.1889 0.0985 0.032 Uiso 1 1 calc R U . . .
C5A C 0.5652(3) 0.11734(9) 0.1239(2) 0.0210(5) Uani 1 1 d . . . . .
C6A C 0.2119(3) 0.13263(10) -0.1050(2) 0.0269(6) Uani 1 1 d . . . . .
H6A H 0.1873 0.1622 -0.1594 0.032 Uiso 1 1 calc R U . . .
C7A C 0.6492(3) 0.08506(9) 0.2248(2) 0.0204(5) Uani 1 1 d . . . . .
C8A C 0.8045(3) 0.05819(9) 0.2155(2) 0.0236(6) Uani 1 1 d . . . . .
C9A C 0.8741(3) 0.02448(9) 0.3079(2) 0.0284(6) Uani 1 1 d . . . . .
H9A H 0.9779 0.0054 0.3021 0.034 Uiso 1 1 calc R U . . .
C10A C 0.7936(3) 0.01848(9) 0.4083(2) 0.0304(6) Uani 1 1 d . . . . .
H10A H 0.8421 -0.0049 0.4705 0.037 Uiso 1 1 calc R U . . .
C11A C 0.6437(3) 0.04625(9) 0.4183(2) 0.0270(6) Uani 1 1 d . . . . .
H11A H 0.5906 0.0424 0.4879 0.032 Uiso 1 1 calc R U . . .
C12A C 0.5694(3) 0.07976(9) 0.3279(2) 0.0215(5) Uani 1 1 d . . . . .
C13A C 0.8963(3) 0.06414(10) 0.1083(2) 0.0346(7) Uani 1 1 d . . . . .
H13A H 0.8159 0.0581 0.0375 0.052 Uiso 1 1 calc R U . . .
H13B H 0.9879 0.0365 0.1113 0.052 Uiso 1 1 calc R U . . .
H13C H 0.9446 0.1017 0.1063 0.052 Uiso 1 1 calc R U . . .
C14A C 0.4048(3) 0.10966(10) 0.3419(2) 0.0347(6) Uani 1 1 d . . . . .
H14A H 0.3119 0.0930 0.2891 0.052 Uiso 1 1 calc R U . . .
H14B H 0.4157 0.1492 0.3223 0.052 Uiso 1 1 calc R U . . .
H14C H 0.3800 0.1062 0.4234 0.052 Uiso 1 1 calc R U . . .
O1B O 0.7001(2) 0.49550(6) 0.35825(16) 0.0345(4) Uani 1 1 d . . . . .
N1B N 0.7750(2) 0.38728(7) 0.26282(17) 0.0219(5) Uani 1 1 d . . . . .
C2B C 0.6180(3) 0.41289(9) 0.2543(2) 0.0203(5) Uani 1 1 d . . . . .
C3B C 0.5035(3) 0.37863(9) 0.1889(2) 0.0242(6) Uani 1 1 d . . . . .
H3B H 0.3854 0.3856 0.1689 0.029 Uiso 1 1 calc R U . . .
C4B C 0.5918(3) 0.33199(9) 0.1574(2) 0.0260(6) Uani 1 1 d . . . . .
H4B H 0.5448 0.3014 0.1118 0.031 Uiso 1 1 calc R U . . .
C5B C 0.7595(3) 0.33784(9) 0.2040(2) 0.0208(5) Uani 1 1 d . . . . .
C6B C 0.5886(3) 0.46513(9) 0.3073(2) 0.0258(6) Uani 1 1 d . . . . .
H6B H 0.4741 0.4776 0.3032 0.031 Uiso 1 1 calc R U . . .
C7B C 0.9059(3) 0.30032(9) 0.1954(2) 0.0214(5) Uani 1 1 d . . . . .
C8B C 0.9195(3) 0.25032(9) 0.2601(2) 0.0243(6) Uani 1 1 d . . . . .
C9B C 1.0538(3) 0.21468(10) 0.2455(2) 0.0323(6) Uani 1 1 d . . . . .
H9B H 1.0656 0.1809 0.2890 0.039 Uiso 1 1 calc R U . . .
C10B C 1.1706(3) 0.22750(10) 0.1688(2) 0.0329(6) Uani 1 1 d . . . . .
H10B H 1.2609 0.2024 0.1593 0.040 Uiso 1 1 calc R U . . .
C11B C 1.1559(3) 0.27666(9) 0.1062(2) 0.0288(6) Uani 1 1 d . . . . .
H11B H 1.2359 0.2851 0.0532 0.035 Uiso 1 1 calc R U . . .
C12B C 1.0259(3) 0.31401(9) 0.1195(2) 0.0225(5) Uani 1 1 d . . . . .
C13B C 0.7942(3) 0.23513(10) 0.3447(2) 0.0350(7) Uani 1 1 d . . . . .
H13D H 0.8111 0.2597 0.4134 0.053 Uiso 1 1 calc R U . . .
H13E H 0.8123 0.1963 0.3698 0.053 Uiso 1 1 calc R U . . .
H13F H 0.6779 0.2395 0.3056 0.053 Uiso 1 1 calc R U . . .
C14B C 1.0147(3) 0.36827(9) 0.0536(2) 0.0324(6) Uani 1 1 d . . . . .
H14D H 1.0498 0.3988 0.1079 0.049 Uiso 1 1 calc R U . . .
H14E H 0.8972 0.3744 0.0182 0.049 Uiso 1 1 calc R U . . .
H14F H 1.0900 0.3670 -0.0084 0.049 Uiso 1 1 calc R U . . .
H1A H 0.357(3) 0.0655(11) 0.076(3) 0.066(9) Uiso 1 1 d . . . . .
H1B H 0.873(3) 0.4004(9) 0.303(2) 0.030(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C6A 1.232(3) . ?
N1A C5A 1.365(3) . ?
N1A C2A 1.378(3) . ?
N1A H1A 0.96(3) . ?
C2A C3A 1.378(3) . ?
C2A C6A 1.428(3) . ?
C3A C4A 1.400(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.386(3) . ?
C4A H4A 0.9500 . ?
C5A C7A 1.481(3) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.403(3) . ?
C7A C12A 1.410(3) . ?
C8A C9A 1.392(3) . ?
C8A C13A 1.507(3) . ?
C9A C10A 1.387(3) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.377(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.386(3) . ?
C11A H11A 0.9500 . ?
C12A C14A 1.512(3) . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
O1B C6B 1.236(3) . ?
N1B C5B 1.362(3) . ?
N1B C2B 1.379(3) . ?
N1B H1B 0.91(2) . ?
C2B C3B 1.377(3) . ?
C2B C6B 1.423(3) . ?
C3B C4B 1.389(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.377(3) . ?
C4B H4B 0.9500 . ?
C5B C7B 1.479(3) . ?
C6B H6B 0.9500 . ?
C7B C12B 1.401(3) . ?
C7B C8B 1.407(3) . ?
C8B C9B 1.389(3) . ?
C8B C13B 1.511(3) . ?
C9B C10B 1.384(3) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.378(3) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.386(3) . ?
C11B H11B 0.9500 . ?
C12B C14B 1.502(3) . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5A N1A C2A 109.56(18) . . ?
C5A N1A H1A 126.3(17) . . ?
C2A N1A H1A 124.1(18) . . ?
C3A C2A N1A 107.4(2) . . ?
C3A C2A C6A 127.5(2) . . ?
N1A C2A C6A 125.1(2) . . ?
C2A C3A C4A 107.90(19) . . ?
C2A C3A H3A 126.1 . . ?
C4A C3A H3A 126.1 . . ?
C5A C4A C3A 107.5(2) . . ?
C5A C4A H4A 126.2 . . ?
C3A C4A H4A 126.2 . . ?
N1A C5A C4A 107.6(2) . . ?
N1A C5A C7A 121.07(18) . . ?
C4A C5A C7A 131.3(2) . . ?
O1A C6A C2A 125.9(2) . . ?
O1A C6A H6A 117.0 . . ?
C2A C6A H6A 117.0 . . ?
C8A C7A C12A 120.4(2) . . ?
C8A C7A C5A 119.8(2) . . ?
C12A C7A C5A 119.8(2) . . ?
C9A C8A C7A 118.7(2) . . ?
C9A C8A C13A 119.3(2) . . ?
C7A C8A C13A 122.0(2) . . ?
C10A C9A C8A 120.8(2) . . ?
C10A C9A H9A 119.6 . . ?
C8A C9A H9A 119.6 . . ?
C11A C10A C9A 120.2(2) . . ?
C11A C10A H10A 119.9 . . ?
C9A C10A H10A 119.9 . . ?
C10A C11A C12A 120.8(2) . . ?
C10A C11A H11A 119.6 . . ?
C12A C11A H11A 119.6 . . ?
C11A C12A C7A 119.1(2) . . ?
C11A C12A C14A 119.3(2) . . ?
C7A C12A C14A 121.6(2) . . ?
C8A C13A H13A 109.5 . . ?
C8A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C8A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C12A C14A H14A 109.5 . . ?
C12A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C12A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C5B N1B C2B 108.99(19) . . ?
C5B N1B H1B 124.9(14) . . ?
C2B N1B H1B 126.0(14) . . ?
C3B C2B N1B 107.52(19) . . ?
C3B C2B C6B 128.9(2) . . ?
N1B C2B C6B 123.6(2) . . ?
C2B C3B C4B 107.7(2) . . ?
C2B C3B H3B 126.2 . . ?
C4B C3B H3B 126.2 . . ?
C5B C4B C3B 108.0(2) . . ?
C5B C4B H4B 126.0 . . ?
C3B C4B H4B 126.0 . . ?
N1B C5B C4B 107.86(19) . . ?
N1B C5B C7B 122.5(2) . . ?
C4B C5B C7B 129.6(2) . . ?
O1B C6B C2B 125.2(2) . . ?
O1B C6B H6B 117.4 . . ?
C2B C6B H6B 117.4 . . ?
C12B C7B C8B 120.8(2) . . ?
C12B C7B C5B 119.5(2) . . ?
C8B C7B C5B 119.65(19) . . ?
C9B C8B C7B 118.2(2) . . ?
C9B C8B C13B 119.9(2) . . ?
C7B C8B C13B 121.9(2) . . ?
C10B C9B C8B 121.2(2) . . ?
C10B C9B H9B 119.4 . . ?
C8B C9B H9B 119.4 . . ?
C11B C10B C9B 120.0(2) . . ?
C11B C10B H10B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C10B C11B C12B 120.9(2) . . ?
C10B C11B H11B 119.5 . . ?
C12B C11B H11B 119.5 . . ?
C11B C12B C7B 118.9(2) . . ?
C11B C12B C14B 120.3(2) . . ?
C7B C12B C14B 120.8(2) . . ?
C8B C13B H13D 109.5 . . ?
C8B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C8B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C12B C14B H14D 109.5 . . ?
C12B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C12B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5A N1A C2A C3A -0.1(2) . . . . ?
C5A N1A C2A C6A 179.7(2) . . . . ?
N1A C2A C3A C4A 0.2(2) . . . . ?
C6A C2A C3A C4A -179.6(2) . . . . ?
C2A C3A C4A C5A -0.2(3) . . . . ?
C2A N1A C5A C4A -0.1(2) . . . . ?
C2A N1A C5A C7A 178.69(19) . . . . ?
C3A C4A C5A N1A 0.2(3) . . . . ?
C3A C4A C5A C7A -178.4(2) . . . . ?
C3A C2A C6A O1A 177.5(2) . . . . ?
N1A C2A C6A O1A -2.3(4) . . . . ?
N1A C5A C7A C8A 111.9(2) . . . . ?
C4A C5A C7A C8A -69.6(3) . . . . ?
N1A C5A C7A C12A -65.7(3) . . . . ?
C4A C5A C7A C12A 112.8(3) . . . . ?
C12A C7A C8A C9A 2.7(3) . . . . ?
C5A C7A C8A C9A -174.9(2) . . . . ?
C12A C7A C8A C13A -178.2(2) . . . . ?
C5A C7A C8A C13A 4.2(3) . . . . ?
C7A C8A C9A C10A -1.4(3) . . . . ?
C13A C8A C9A C10A 179.4(2) . . . . ?
C8A C9A C10A C11A -0.4(4) . . . . ?
C9A C10A C11A C12A 1.1(3) . . . . ?
C10A C11A C12A C7A 0.2(3) . . . . ?
C10A C11A C12A C14A -180.0(2) . . . . ?
C8A C7A C12A C11A -2.1(3) . . . . ?
C5A C7A C12A C11A 175.5(2) . . . . ?
C8A C7A C12A C14A 178.1(2) . . . . ?
C5A C7A C12A C14A -4.3(3) . . . . ?
C5B N1B C2B C3B -0.1(2) . . . . ?
C5B N1B C2B C6B 179.2(2) . . . . ?
N1B C2B C3B C4B -0.1(3) . . . . ?
C6B C2B C3B C4B -179.3(2) . . . . ?
C2B C3B C4B C5B 0.2(3) . . . . ?
C2B N1B C5B C4B 0.2(3) . . . . ?
C2B N1B C5B C7B 179.4(2) . . . . ?
C3B C4B C5B N1B -0.3(3) . . . . ?
C3B C4B C5B C7B -179.4(2) . . . . ?
C3B C2B C6B O1B -174.8(2) . . . . ?
N1B C2B C6B O1B 6.1(4) . . . . ?
N1B C5B C7B C12B -75.0(3) . . . . ?
C4B C5B C7B C12B 104.0(3) . . . . ?
N1B C5B C7B C8B 107.3(3) . . . . ?
C4B C5B C7B C8B -73.7(3) . . . . ?
C12B C7B C8B C9B -0.8(3) . . . . ?
C5B C7B C8B C9B 176.8(2) . . . . ?
C12B C7B C8B C13B 178.6(2) . . . . ?
C5B C7B C8B C13B -3.8(3) . . . . ?
C7B C8B C9B C10B -0.5(4) . . . . ?
C13B C8B C9B C10B -179.9(2) . . . . ?
C8B C9B C10B C11B 0.7(4) . . . . ?
C9B C10B C11B C12B 0.5(4) . . . . ?
C10B C11B C12B C7B -1.8(4) . . . . ?
C10B C11B C12B C14B 178.0(2) . . . . ?
C8B C7B C12B C11B 2.0(3) . . . . ?
C5B C7B C12B C11B -175.6(2) . . . . ?
C8B C7B C12B C14B -177.9(2) . . . . ?
C5B C7B C12B C14B 4.5(3) . . . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.049

_shelxl_version_number           2014-3

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Diethyl ether'
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1064031'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2015-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        5-(4-methoxyphenyl)-1H-pyrrole-2-carbaldehyde
_chemical_name_common            5-(4-methoxyphenyl)-2-formylpyrrole
_chemical_formula_moiety         'C12 H11 N O2'
_chemical_formula_sum            'C12 H11 N O2'
_chemical_melting_point          ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         201.22

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.5376(3)
_cell_length_b                   6.4429(3)
_cell_length_c                   27.5008(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     981.18(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1086
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      23.56
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'SADABS, (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4846
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.248
_diffrn_reflns_theta_max         25.684
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             1804
_reflns_number_gt                1395
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.599
_reflns_Friedel_fraction_max     0.923
_reflns_Friedel_fraction_full    0.933

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer

_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)+(0.0387P)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 ?
_refine_ls_abs_structure_Flack   ?
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P 21 21 21'
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1804
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0818
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0546(4) 0.9736(3) 0.23435(7) 0.0269(6) Uani 1 1 d . . . . .
O2 O 0.3180(4) -0.0200(3) 0.46574(7) 0.0287(6) Uani 1 1 d . . . . .
N1 N 0.2866(5) 0.7461(4) 0.31174(9) 0.0201(6) Uani 1 1 d . . . . .
C2 C 0.3635(6) 0.9334(4) 0.29235(10) 0.0193(7) Uani 1 1 d . . . . .
C3 C 0.5702(6) 0.9908(4) 0.31695(10) 0.0226(7) Uani 1 1 d . . . . .
H3 H 0.6622 1.1131 0.3115 0.027 Uiso 1 1 calc R U . . .
C4 C 0.6196(6) 0.8374(4) 0.35117(11) 0.0241(8) Uani 1 1 d . . . . .
H4 H 0.7523 0.8359 0.3731 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4402(6) 0.6865(4) 0.34765(10) 0.0191(7) Uani 1 1 d . . . . .
C6 C 0.2361(6) 1.0404(4) 0.25509(10) 0.0219(7) Uani 1 1 d . . . . .
H6 H 0.2949 1.1727 0.2455 0.026 Uiso 1 1 calc R U . . .
C7 C 0.4031(5) 0.4988(4) 0.37691(10) 0.0187(7) Uani 1 1 d . . . . .
C8 C 0.5681(6) 0.4459(4) 0.41293(10) 0.0245(7) Uani 1 1 d . . . . .
H8 H 0.7068 0.5302 0.4177 0.029 Uiso 1 1 calc R U . . .
C9 C 0.5346(6) 0.2731(4) 0.44202(11) 0.0254(8) Uani 1 1 d . . . . .
H9 H 0.6495 0.2398 0.4665 0.031 Uiso 1 1 calc R U . . .
C10 C 0.3337(6) 0.1489(4) 0.43546(10) 0.0217(7) Uani 1 1 d . . . . .
C11 C 0.1661(6) 0.1994(4) 0.40037(10) 0.0246(8) Uani 1 1 d . . . . .
H11 H 0.0266 0.1156 0.3961 0.030 Uiso 1 1 calc R U . . .
C12 C 0.2012(6) 0.3728(4) 0.37121(10) 0.0235(8) Uani 1 1 d . . . . .
H12 H 0.0853 0.4060 0.3470 0.028 Uiso 1 1 calc R U . . .
C13 C 0.1108(6) -0.1506(5) 0.46064(11) 0.0324(9) Uani 1 1 d . . . . .
H13A H -0.0356 -0.0701 0.4674 0.049 Uiso 1 1 calc R U . . .
H13B H 0.1220 -0.2663 0.4837 0.049 Uiso 1 1 calc R U . . .
H13C H 0.1038 -0.2050 0.4274 0.049 Uiso 1 1 calc R U . . .
H1 H 0.167(7) 0.668(6) 0.2998(12) 0.054(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.233(3) . ?
O2 C10 1.373(3) . ?
O2 C13 1.430(4) . ?
N1 C5 1.359(4) . ?
N1 C2 1.386(4) . ?
N1 H1 0.89(4) . ?
C2 C3 1.380(4) . ?
C2 C6 1.422(4) . ?
C3 C4 1.392(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(4) . ?
C4 H4 0.9500 . ?
C5 C7 1.467(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(4) . ?
C7 C12 1.390(4) . ?
C8 C9 1.384(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(4) . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 C13 117.3(2) . . ?
C5 N1 C2 109.5(3) . . ?
C5 N1 H1 125(2) . . ?
C2 N1 H1 125(2) . . ?
C3 C2 N1 107.4(3) . . ?
C3 C2 C6 129.4(3) . . ?
N1 C2 C6 123.1(3) . . ?
C2 C3 C4 107.7(3) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
C3 C4 C5 108.0(3) . . ?
C3 C4 H4 126.0 . . ?
C5 C4 H4 126.0 . . ?
N1 C5 C4 107.4(2) . . ?
N1 C5 C7 123.0(3) . . ?
C4 C5 C7 129.6(3) . . ?
O1 C6 C2 124.6(3) . . ?
O1 C6 H6 117.7 . . ?
C2 C6 H6 117.7 . . ?
C8 C7 C12 117.8(3) . . ?
C8 C7 C5 120.1(3) . . ?
C12 C7 C5 122.1(3) . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
O2 C10 C11 124.7(3) . . ?
O2 C10 C9 115.5(3) . . ?
C11 C10 C9 119.8(3) . . ?
C10 C11 C12 120.0(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 121.1(3) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 C3 0.0(3) . . . . ?
C5 N1 C2 C6 -177.8(3) . . . . ?
N1 C2 C3 C4 0.3(3) . . . . ?
C6 C2 C3 C4 178.0(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C2 N1 C5 C4 -0.4(3) . . . . ?
C2 N1 C5 C7 177.3(3) . . . . ?
C3 C4 C5 N1 0.6(3) . . . . ?
C3 C4 C5 C7 -176.9(3) . . . . ?
C3 C2 C6 O1 178.2(3) . . . . ?
N1 C2 C6 O1 -4.4(4) . . . . ?
N1 C5 C7 C8 179.6(3) . . . . ?
C4 C5 C7 C8 -3.3(5) . . . . ?
N1 C5 C7 C12 -2.8(4) . . . . ?
C4 C5 C7 C12 174.3(3) . . . . ?
C12 C7 C8 C9 0.5(4) . . . . ?
C5 C7 C8 C9 178.2(3) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C13 O2 C10 C11 -0.8(4) . . . . ?
C13 O2 C10 C9 179.0(3) . . . . ?
C8 C9 C10 O2 179.3(3) . . . . ?
C8 C9 C10 C11 -0.8(4) . . . . ?
O2 C10 C11 C12 -179.2(3) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
C10 C11 C12 C7 -0.4(4) . . . . ?
C8 C7 C12 C11 -0.3(4) . . . . ?
C5 C7 C12 C11 -178.0(3) . . . . ?

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.047

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Tetrahydrofurane'
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1064032'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2015-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        5-(4-fluorophenyl)-1H-pyrrole-2-carbaldehyde
_chemical_name_common            5-(4-fluorophenyl)-2-formylpyrrole
_chemical_formula_moiety         'C11 H8 F N O'
_chemical_formula_sum            'C11 H8 F N O'
_chemical_melting_point          ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         189.18

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.5758(8)
_cell_length_b                   6.3791(6)
_cell_length_c                   24.493(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     871.20(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    417
_cell_measurement_theta_min      3.75
_cell_measurement_theta_max      20.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2893
_diffrn_reflns_av_unetI/netI     0.0954
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.663
_diffrn_reflns_theta_max         25.581
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             1574
_reflns_number_gt                1049
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.619
_reflns_Friedel_fraction_max     0.939
_reflns_Friedel_fraction_full    0.943

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer

_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)+(0.0307P)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 ?
_refine_ls_abs_structure_Flack   ?
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P 21 21 21'
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1574
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.948
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.3207(5) 0.1871(4) 0.50960(10) 0.0411(8) Uani 1 1 d . . . . .
O1 O 0.0558(5) -0.8057(4) 0.76884(11) 0.0266(8) Uani 1 1 d . . . . .
N1 N 0.2853(6) -0.5805(5) 0.68069(14) 0.0184(9) Uani 1 1 d . . . . .
C2 C 0.3617(7) -0.7679(6) 0.70318(16) 0.0192(11) Uani 1 1 d . . . . .
C3 C 0.5655(8) -0.8286(6) 0.67571(16) 0.0225(10) Uani 1 1 d . . . . .
H3 H 0.6558 -0.9525 0.6822 0.027 Uiso 1 1 calc R U . . .
C4 C 0.6160(8) -0.6750(6) 0.63650(17) 0.0216(10) Uani 1 1 d . . . . .
H4 H 0.7478 -0.6746 0.6119 0.026 Uiso 1 1 calc R U . . .
C5 C 0.4366(8) -0.5224(6) 0.64019(16) 0.0184(10) Uani 1 1 d . . . . .
C6 C 0.2325(8) -0.8740(6) 0.74520(17) 0.0223(11) Uani 1 1 d . . . . .
H6 H 0.2884 -1.0088 0.7557 0.027 Uiso 1 1 calc R U . . .
C7 C 0.4031(7) -0.3324(6) 0.60702(16) 0.0177(10) Uani 1 1 d . . . . .
C8 C 0.5775(8) -0.2780(6) 0.56868(16) 0.0211(10) Uani 1 1 d . . . . .
H8 H 0.7173 -0.3620 0.5652 0.025 Uiso 1 1 calc R U . . .
C9 C 0.5496(8) -0.1037(6) 0.53575(16) 0.0238(11) Uani 1 1 d . . . . .
H9 H 0.6672 -0.0677 0.5093 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3476(9) 0.0156(6) 0.54236(17) 0.0248(11) Uani 1 1 d . . . . .
C11 C 0.1730(8) -0.0322(6) 0.57917(16) 0.0246(11) Uani 1 1 d . . . . .
H11 H 0.0342 0.0532 0.5824 0.030 Uiso 1 1 calc R U . . .
C12 C 0.2015(8) -0.2076(6) 0.61175(18) 0.0235(10) Uani 1 1 d . . . . .
H12 H 0.0812 -0.2426 0.6377 0.028 Uiso 1 1 calc R U . . .
H1 H 0.161(8) -0.505(5) 0.6923(17) 0.030(13) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C10 1.365(4) . ?
O1 C6 1.223(5) . ?
N1 C5 1.354(5) . ?
N1 C2 1.383(5) . ?
N1 H1 0.89(4) . ?
C2 C3 1.376(5) . ?
C2 C6 1.427(5) . ?
C3 C4 1.401(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(5) . ?
C4 H4 0.9500 . ?
C5 C7 1.471(5) . ?
C6 H6 0.9500 . ?
C7 C12 1.382(5) . ?
C7 C8 1.395(6) . ?
C8 C9 1.383(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.369(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.361(6) . ?
C11 C12 1.383(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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
C5 N1 C2 109.7(3) . . ?
C5 N1 H1 125(3) . . ?
C2 N1 H1 126(3) . . ?
C3 C2 N1 107.6(4) . . ?
C3 C2 C6 129.5(4) . . ?
N1 C2 C6 122.8(4) . . ?
C2 C3 C4 107.7(4) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
C5 C4 C3 107.4(4) . . ?
C5 C4 H4 126.3 . . ?
C3 C4 H4 126.3 . . ?
N1 C5 C4 107.6(3) . . ?
N1 C5 C7 123.5(4) . . ?
C4 C5 C7 128.9(4) . . ?
O1 C6 C2 125.4(4) . . ?
O1 C6 H6 117.3 . . ?
C2 C6 H6 117.3 . . ?
C12 C7 C8 118.7(3) . . ?
C12 C7 C5 122.1(4) . . ?
C8 C7 C5 119.2(4) . . ?
C9 C8 C7 120.9(4) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C10 C9 C8 118.1(4) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C11 C10 F1 119.4(4) . . ?
C11 C10 C9 122.8(4) . . ?
F1 C10 C9 117.8(4) . . ?
C10 C11 C12 118.8(4) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C7 C12 C11 120.7(4) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?

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
C5 N1 C2 C3 -0.3(5) . . . . ?
C5 N1 C2 C6 -177.1(4) . . . . ?
N1 C2 C3 C4 0.8(5) . . . . ?
C6 C2 C3 C4 177.3(4) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C2 N1 C5 C4 -0.3(5) . . . . ?
C2 N1 C5 C7 178.5(3) . . . . ?
C3 C4 C5 N1 0.8(5) . . . . ?
C3 C4 C5 C7 -178.0(4) . . . . ?
C3 C2 C6 O1 177.6(4) . . . . ?
N1 C2 C6 O1 -6.4(7) . . . . ?
N1 C5 C7 C12 -5.7(6) . . . . ?
C4 C5 C7 C12 172.9(4) . . . . ?
N1 C5 C7 C8 175.7(4) . . . . ?
C4 C5 C7 C8 -5.7(6) . . . . ?
C12 C7 C8 C9 -0.4(6) . . . . ?
C5 C7 C8 C9 178.3(4) . . . . ?
C7 C8 C9 C10 0.9(6) . . . . ?
C8 C9 C10 C11 -1.1(6) . . . . ?
C8 C9 C10 F1 -179.8(4) . . . . ?
F1 C10 C11 C12 179.4(4) . . . . ?
C9 C10 C11 C12 0.7(7) . . . . ?
C8 C7 C12 C11 0.0(6) . . . . ?
C5 C7 C12 C11 -178.7(4) . . . . ?
C10 C11 C12 C7 -0.1(6) . . . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.050

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
