# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_JBR380P01
_database_code_depnum_ccdc_archive 'CCDC 1956971'
loop_
_audit_author_name
_audit_author_address
'Vincent Dorcet'
;ISCR 
France
;
_audit_update_record             
;
2019-10-01 deposited with the CCDC.	2020-07-28 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 27 juin 2019                                             #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C11 H11 N O2'
_chemical_formula_sum            'C11 H11 N O2'
_chemical_formula_weight         189.21
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration rm/ad/rmad/syn/unk/.

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


_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.5291(8)
_cell_length_b                   7.4902(8)
_cell_length_c                   17.0281(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     960.29(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6696
_cell_measurement_theta_min      5.1951
_cell_measurement_theta_max      74.1041
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             400
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.862

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

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_reflns_av_r_equivalents  0.0430
_diffrn_reflns_av_uneti/neti     0.0361
_diffrn_reflns_number            7285
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         6.456
_diffrn_reflns_theta_max         74.104
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_reflns_number_total             1916
_reflns_number_gt                1865
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.989

_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.
;

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

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017_1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0660P)²+0.1138P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2017_1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.068(9)
_refine_ls_number_reflns         1916
_refine_ls_number_parameters     134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 
;
Flack x determined using 751 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(12)

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.8784(2) 0.6703(3) 0.42485(11) 0.0199(5) Uani 1 1 d . . . . .
C2 C 0.8610(3) 0.8040(3) 0.48008(12) 0.0256(5) Uani 1 1 d . . . . .
H2 H 0.871165 0.926522 0.466420 0.031 Uiso 1 1 calc R U . . .
C3 C 0.8275(3) 0.7493(3) 0.55746(12) 0.0305(6) Uani 1 1 d . . . . .
H3 H 0.812997 0.837253 0.597145 0.037 Uiso 1 1 calc R U . . .
C4 C 0.8151(3) 0.5712(3) 0.57751(12) 0.0301(5) Uani 1 1 d . . . . .
H4 H 0.794804 0.538613 0.630674 0.036 Uiso 1 1 calc R U . . .
C5 C 0.8322(3) 0.4383(3) 0.52035(11) 0.0247(5) Uani 1 1 d . . . . .
H5 H 0.822414 0.315601 0.533749 0.030 Uiso 1 1 calc R U . . .
C6 C 0.8639(2) 0.4909(3) 0.44348(10) 0.0189(5) Uani 1 1 d . . . . .
C7 C 0.8880(2) 0.3805(3) 0.37044(11) 0.0174(4) Uani 1 1 d . . . . .
C8 C 0.9248(2) 0.5279(3) 0.30850(11) 0.0176(4) Uani 1 1 d . . . . .
C9 C 0.7245(2) 0.2686(3) 0.34752(12) 0.0209(4) Uani 1 1 d . . . . .
H9A H 0.748126 0.210384 0.296383 0.025 Uiso 1 1 calc R U . . .
H9B H 0.708354 0.173100 0.387060 0.025 Uiso 1 1 calc R U . . .
C10 C 0.5553(3) 0.3722(3) 0.34124(13) 0.0252(5) Uani 1 1 d . . . . .
H10 H 0.523093 0.445489 0.384496 0.030 Uiso 1 1 calc R U . . .
C11 C 0.4478(3) 0.3696(3) 0.28060(14) 0.0319(5) Uani 1 1 d . . . . .
H11A H 0.475422 0.297932 0.236206 0.038 Uiso 1 1 calc R U . . .
H11B H 0.342477 0.439352 0.281067 0.038 Uiso 1 1 calc R U . . .
N1 N 0.9145(2) 0.6879(2) 0.34334(9) 0.0204(4) Uani 1 1 d . . . . .
H1N H 0.937(3) 0.786(4) 0.3193(15) 0.024 Uiso 1 1 d . U . . .
O1 O 0.96210(17) 0.50074(19) 0.23869(8) 0.0220(4) Uani 1 1 d . . . . .
O2 O 1.04004(17) 0.2697(2) 0.37794(8) 0.0228(4) Uani 1 1 d . . . . .
H2O H 1.040(4) 0.192(4) 0.3398(16) 0.027 Uiso 1 1 d . U . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.380(3) . ?
C1 C6 1.385(3) . ?
C1 N1 1.421(2) . ?
C2 C3 1.403(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.505(3) . ?
C7 O2 1.420(2) . ?
C7 C9 1.540(3) . ?
C7 C8 1.552(3) . ?
C8 O1 1.238(2) . ?
C8 N1 1.339(3) . ?
C9 C10 1.495(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.312(3) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9500 . ?
C11 H11B 0.9500 . ?
N1 H1N 0.86(3) . ?
O2 H2O 0.87(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.72(18) . . ?
C2 C1 N1 128.08(19) . . ?
C6 C1 N1 109.20(17) . . ?
C1 C2 C3 116.4(2) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 H2 121.8 . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 120.64(19) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 118.1(2) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C1 C6 C5 120.34(19) . . ?
C1 C6 C7 109.55(16) . . ?
C5 C6 C7 130.12(19) . . ?
O2 C7 C6 110.13(14) . . ?
O2 C7 C9 110.45(16) . . ?
C6 C7 C9 114.35(15) . . ?
O2 C7 C8 109.46(14) . . ?
C6 C7 C8 101.07(15) . . ?
C9 C7 C8 110.97(15) . . ?
O1 C8 N1 125.83(18) . . ?
O1 C8 C7 125.17(17) . . ?
N1 C8 C7 108.98(15) . . ?
C10 C9 C7 114.66(16) . . ?
C10 C9 H9A 108.6 . . ?
C7 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C7 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 125.0(2) . . ?
C11 C10 H10 117.5 . . ?
C9 C10 H10 117.5 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C8 N1 C1 111.16(17) . . ?
C8 N1 H1N 123.0(17) . . ?
C1 N1 H1N 125.6(17) . . ?
C7 O2 H2O 108.9(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.0(3) . . . . ?
N1 C1 C2 C3 -179.09(19) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
N1 C1 C6 C5 178.71(17) . . . . ?
C2 C1 C6 C7 179.58(17) . . . . ?
N1 C1 C6 C7 -1.2(2) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 C7 179.99(18) . . . . ?
C1 C6 C7 O2 117.57(17) . . . . ?
C5 C6 C7 O2 -62.3(3) . . . . ?
C1 C6 C7 C9 -117.37(18) . . . . ?
C5 C6 C7 C9 62.8(3) . . . . ?
C1 C6 C7 C8 1.89(17) . . . . ?
C5 C6 C7 C8 -177.95(19) . . . . ?
O2 C7 C8 O1 60.1(2) . . . . ?
C6 C7 C8 O1 176.28(17) . . . . ?
C9 C7 C8 O1 -62.1(2) . . . . ?
O2 C7 C8 N1 -118.23(16) . . . . ?
C6 C7 C8 N1 -2.05(17) . . . . ?
C9 C7 C8 N1 119.61(16) . . . . ?
O2 C7 C9 C10 177.67(15) . . . . ?
C6 C7 C9 C10 52.8(2) . . . . ?
C8 C7 C9 C10 -60.7(2) . . . . ?
C7 C9 C10 C11 128.3(2) . . . . ?
O1 C8 N1 C1 -176.80(16) . . . . ?
C7 C8 N1 C1 1.5(2) . . . . ?
C2 C1 N1 C8 178.95(18) . . . . ?
C6 C1 N1 C8 -0.3(2) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR JBR380P01                                              #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_JBR49P01
_database_code_depnum_ccdc_archive 'CCDC 1984556'
loop_
_audit_author_name
_audit_author_address
'Vincent DORCET'
;ISCR 
France
;
_audit_update_record             
;
2020-02-17 deposited with the CCDC.	2020-07-28 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 06 decembre 2019                                         #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H13 N O2'
_chemical_formula_sum            'C12 H13 N O2'
_chemical_formula_weight         203.23
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration rm/ad/rmad/syn/unk/.

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


_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.3607(8)
_cell_length_b                   8.0406(11)
_cell_length_c                   17.598(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1041.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2143
_cell_measurement_theta_min      5.0265
_cell_measurement_theta_max      74.4807
_cell_measurement_wavelength     1.54184


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0216660
_diffrn_orient_matrix_UB_21      0.0210248
_diffrn_orient_matrix_UB_31      -0.1324593
_diffrn_orient_matrix_UB_12      0.0739528
_diffrn_orient_matrix_UB_22      -0.0999229
_diffrn_orient_matrix_UB_32      -0.0037641
_diffrn_orient_matrix_UB_13      -0.0447802
_diffrn_orient_matrix_UB_23      -0.0326705
_diffrn_orient_matrix_UB_33      -0.0125102


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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             432
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_T_max  0.854

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

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_reflns_av_r_equivalents  0.0566
_diffrn_reflns_av_uneti/neti     0.0766
_diffrn_reflns_number            4737
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         6.519
_diffrn_reflns_theta_max         74.603
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.968
_reflns_number_total             1990
_reflns_number_gt                1408
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.635
_reflns_Friedel_fraction_max     0.885
_reflns_Friedel_fraction_full    0.923

_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.
;

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

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017_1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0636P)²+4.4547P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017_1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.023(4)
_refine_ls_number_reflns         1990
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0830
_refine_ls_wR_factor_ref         0.2428
_refine_ls_wR_factor_gt          0.2006
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 
;
Flack x determined using 415 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.6706(9) 0.3307(9) 0.5380(4) 0.0273(16) Uani 1 1 d . . . . .
C2 C 0.7075(11) 0.2596(12) 0.4683(5) 0.0370(19) Uani 1 1 d . . . . .
H2 H 0.725546 0.143252 0.462493 0.044 Uiso 1 1 calc R U . . .
C3 C 0.7166(11) 0.3691(13) 0.4067(5) 0.042(2) Uani 1 1 d . . . . .
H3 H 0.741188 0.325532 0.357531 0.051 Uiso 1 1 calc R U . . .
C4 C 0.6911(11) 0.5387(12) 0.4148(5) 0.043(2) Uani 1 1 d . . . . .
H4 H 0.698266 0.609326 0.371579 0.051 Uiso 1 1 calc R U . . .
C5 C 0.6548(11) 0.6067(11) 0.4866(4) 0.0360(19) Uani 1 1 d . . . . .
H5 H 0.637568 0.722981 0.492672 0.043 Uiso 1 1 calc R U . . .
C6 C 0.6445(10) 0.5013(10) 0.5479(4) 0.0300(17) Uani 1 1 d . . . . .
C7 C 0.6095(10) 0.5355(10) 0.6313(5) 0.0318(17) Uani 1 1 d . . . . .
C8 C 0.6083(10) 0.3585(10) 0.6641(4) 0.0331(17) Uani 1 1 d . . . . .
C9 C 0.6706(12) 0.0704(10) 0.6179(5) 0.044(2) Uani 1 1 d . . . . .
H9A H 0.650374 0.041521 0.671306 0.066 Uiso 1 1 calc R U . . .
H9B H 0.793138 0.036206 0.602762 0.066 Uiso 1 1 calc R U . . .
H9C H 0.580900 0.012998 0.586125 0.066 Uiso 1 1 calc R U . . .
C10 C 0.7622(10) 0.6352(11) 0.6678(5) 0.0366(19) Uani 1 1 d . . . . .
H10A H 0.764104 0.747594 0.644842 0.044 Uiso 1 1 calc R U . . .
H10B H 0.734893 0.648573 0.722572 0.044 Uiso 1 1 calc R U . . .
C11 C 0.9472(11) 0.5599(11) 0.6600(5) 0.040(2) Uani 1 1 d . . . . .
H11 H 1.000415 0.561366 0.610782 0.048 Uiso 1 1 calc R U . . .
C12 C 1.0412(11) 0.4931(13) 0.7140(5) 0.051(2) Uani 1 1 d . . . . .
H12A H 0.993465 0.488825 0.764092 0.061 Uiso 1 1 calc R U . . .
H12B H 1.157948 0.448254 0.703545 0.061 Uiso 1 1 calc R U . . .
O1 O 0.4400(8) 0.6144(8) 0.6395(3) 0.0436(15) Uani 1 1 d . . . . .
H1 H 0.425766 0.643248 0.685040 0.065 Uiso 1 1 calc R U . . .
O2 O 0.5718(8) 0.3229(8) 0.7305(3) 0.0443(16) Uani 1 1 d . . . . .
N1 N 0.6518(8) 0.2472(8) 0.6082(4) 0.0321(15) Uani 1 1 d . . . . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.380(11) . ?
C1 C6 1.396(11) . ?
C1 N1 1.413(9) . ?
C2 C3 1.398(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.515(10) . ?
C7 O1 1.408(9) . ?
C7 C10 1.523(11) . ?
C7 C8 1.536(11) . ?
C8 O2 1.232(9) . ?
C8 N1 1.369(10) . ?
C9 N1 1.438(10) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.497(11) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.292(12) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9500 . ?
C12 H12B 0.9500 . ?
O1 H1 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 123.0(7) . . ?
C2 C1 N1 126.8(7) . . ?
C6 C1 N1 110.2(6) . . ?
C1 C2 C3 115.9(8) . . ?
C1 C2 H2 122.0 . . ?
C3 C2 H2 122.0 . . ?
C4 C3 C2 122.3(8) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 120.2(8) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 118.6(8) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 120.0(7) . . ?
C5 C6 C7 131.2(7) . . ?
C1 C6 C7 108.8(6) . . ?
O1 C7 C6 109.4(6) . . ?
O1 C7 C10 111.9(7) . . ?
C6 C7 C10 112.3(6) . . ?
O1 C7 C8 111.9(6) . . ?
C6 C7 C8 101.4(6) . . ?
C10 C7 C8 109.5(6) . . ?
O2 C8 N1 125.5(8) . . ?
O2 C8 C7 125.0(7) . . ?
N1 C8 C7 109.5(6) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 114.8(7) . . ?
C11 C10 H10A 108.6 . . ?
C7 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C7 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C10 126.0(8) . . ?
C12 C11 H11 117.0 . . ?
C10 C11 H11 117.0 . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
C7 O1 H1 109.5 . . ?
C8 N1 C1 109.9(6) . . ?
C8 N1 C9 125.7(7) . . ?
C1 N1 C9 124.3(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
C6 C1 C2 C3 -0.4(11) . . . . ?
N1 C1 C2 C3 179.0(7) . . . . ?
C1 C2 C3 C4 0.3(12) . . . . ?
C2 C3 C4 C5 0.0(13) . . . . ?
C3 C4 C5 C6 -0.3(12) . . . . ?
C4 C5 C6 C1 0.2(11) . . . . ?
C4 C5 C6 C7 179.4(8) . . . . ?
C2 C1 C6 C5 0.2(11) . . . . ?
N1 C1 C6 C5 -179.3(7) . . . . ?
C2 C1 C6 C7 -179.3(7) . . . . ?
N1 C1 C6 C7 1.3(8) . . . . ?
C5 C6 C7 O1 58.9(11) . . . . ?
C1 C6 C7 O1 -121.8(7) . . . . ?
C5 C6 C7 C10 -66.0(10) . . . . ?
C1 C6 C7 C10 113.3(7) . . . . ?
C5 C6 C7 C8 177.2(8) . . . . ?
C1 C6 C7 C8 -3.4(8) . . . . ?
O1 C7 C8 O2 -58.2(10) . . . . ?
C6 C7 C8 O2 -174.7(7) . . . . ?
C10 C7 C8 O2 66.5(10) . . . . ?
O1 C7 C8 N1 121.1(7) . . . . ?
C6 C7 C8 N1 4.6(8) . . . . ?
C10 C7 C8 N1 -114.2(7) . . . . ?
O1 C7 C10 C11 -179.0(7) . . . . ?
C6 C7 C10 C11 -55.4(9) . . . . ?
C8 C7 C10 C11 56.3(9) . . . . ?
C7 C10 C11 C12 -109.1(11) . . . . ?
O2 C8 N1 C1 175.1(7) . . . . ?
C7 C8 N1 C1 -4.1(8) . . . . ?
O2 C8 N1 C9 -3.0(12) . . . . ?
C7 C8 N1 C9 177.7(7) . . . . ?
C2 C1 N1 C8 -177.6(7) . . . . ?
C6 C1 N1 C8 1.8(8) . . . . ?
C2 C1 N1 C9 0.6(12) . . . . ?
C6 C1 N1 C9 -180.0(7) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR JBR49P01                                               #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
