# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 2125364'
loop_
_audit_author_name
_audit_author_address
'Sylvain Bernes'
;Instituto de Fisica, BUAP, Puebla
Mexico
;
_audit_update_record             
;
2021-11-30 deposited with the CCDC.	2022-01-21 downloaded from the CCDC.
;

# Clave Lab.  :  ENR-376-1
# Clave IF-UAP:  ENR-376-1
# Solicitud: 362
# Firma en la Solicitud: Dr. Joel Luis Teran (ICUAP)
# Clave datos : ... \BUAP\Sylvain\ENR-376-1\40mm_1\

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_audit_creation_date             2019-08-30

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          372
_chemical_formula_moiety         'C16 H20 Br N O4'
_chemical_formula_sum            'C16 H20 Br N O4'
_chemical_formula_weight         370.24
_chemical_absolute_configuration ad
_chemical_optical_rotation       ?

_chemical_properties_physical    ?
_chemical_properties_biological  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br 0.1811 1.6452 '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       ?

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                   7.7807(3)
_cell_length_b                   13.9973(7)
_cell_length_c                   15.1800(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1653.24(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    27617
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      24.52

_exptl_crystal_recrystallization_method 
;
Re-crystallisation from solvent: CH2Cl2/Petroleum ether
;

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.150
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -5 5 0.0600
-1 2 -2 0.0450
7 -3 2 0.1450
-1 -5 6 0.1100
0 4 -7 0.1050
-1 -3 5 0.1410
3 5 -1 0.1500
-3 -2 -5 0.1700
3 2 5 0.1760
-3 -5 1 0.1380

_exptl_absorpt_coefficient_mu    1.347
_shelx_estimated_absorpt_T_min   0.698
_shelx_estimated_absorpt_T_max   0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4889
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'X-AREA 1.86 (Stoe & Cie, 2018)'

_diffrn_ambient_temperature      295(1)
_diffrn_ambient_environment      air
_diffrn_measurement_specimen_support Mitegen
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_diffrn_source_current           0.55
_diffrn_source_power             0.03575
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
1149 frames, 50 s/frame, 1 deg./frame, detector distance = 40 mm
;
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            44015
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.321
_diffrn_reflns_theta_max         21.994
_diffrn_reflns_theta_full        19.664
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4137
_reflns_number_gt                2869
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          ?

_computing_data_collection       'X-AREA 1.86 (Stoe & Cie, 2018)'
_computing_cell_refinement       'X-AREA 1.86'
_computing_data_reduction        'X-AREA 1.86'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'

_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)+(0.0448P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1005 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.029(8)
_refine_ls_number_reflns         4137
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.05180(6) 0.54800(4) 0.60851(4) 0.06968(19) Uani 1 1 d . . . . .
O1 O 0.5818(3) 0.3627(2) 0.79794(19) 0.0460(7) Uani 1 1 d . . . . .
C2 C 0.6353(5) 0.3517(3) 0.7088(3) 0.0461(10) Uani 1 1 d . . . . .
H2A H 0.634682 0.284846 0.691867 0.055 Uiso 1 1 calc R U . . .
H2B H 0.750077 0.377104 0.700375 0.055 Uiso 1 1 calc R U . . .
C3 C 0.5037(4) 0.4083(3) 0.6552(3) 0.0379(9) Uani 1 1 d . . . . .
H3A H 0.537237 0.475812 0.654275 0.045 Uiso 1 1 calc R U . . .
N4 N 0.3510(3) 0.3968(2) 0.7111(2) 0.0369(7) Uani 1 1 d . . . . .
C5 C 0.4003(5) 0.3639(3) 0.8013(3) 0.0385(8) Uani 1 1 d . . . . .
C6 C 0.4892(4) 0.3724(3) 0.5621(3) 0.0386(9) Uani 1 1 d . . . . .
C7 C 0.4269(5) 0.2812(3) 0.5432(3) 0.0460(9) Uani 1 1 d . . . . .
H7A H 0.386014 0.243060 0.588762 0.055 Uiso 1 1 calc R U . . .
C8 C 0.4251(6) 0.2467(3) 0.4582(3) 0.0567(11) Uani 1 1 d . . . . .
H8A H 0.383641 0.185625 0.446787 0.068 Uiso 1 1 calc R U . . .
C9 C 0.4847(5) 0.3027(4) 0.3900(3) 0.0621(12) Uani 1 1 d . . . . .
H9A H 0.483460 0.279339 0.332689 0.075 Uiso 1 1 calc R U . . .
C10 C 0.5459(6) 0.3927(4) 0.4066(3) 0.0579(11) Uani 1 1 d . . . . .
H10A H 0.585375 0.430516 0.360503 0.069 Uiso 1 1 calc R U . . .
C11 C 0.5491(6) 0.4273(3) 0.4919(3) 0.0465(9) Uani 1 1 d . . . . .
H11A H 0.591865 0.488273 0.502611 0.056 Uiso 1 1 calc R U . . .
C12 C 0.1892(4) 0.4266(3) 0.6941(3) 0.0400(9) Uani 1 1 d . . . . .
O12 O 0.0685(3) 0.4089(2) 0.74342(19) 0.0539(7) Uani 1 1 d . . . . .
C13 C 0.1681(4) 0.4835(3) 0.6101(3) 0.0497(10) Uani 1 1 d . . . . .
H13A H 0.176349 0.441093 0.559741 0.060 Uiso 1 1 calc R U . . .
H13B H 0.259721 0.530297 0.605672 0.060 Uiso 1 1 calc R U . . .
C14 C 0.3504(5) 0.4352(3) 0.8729(3) 0.0482(10) Uani 1 1 d . . . . .
H14A H 0.400190 0.414820 0.928421 0.058 Uiso 1 1 calc R U . . .
H14B H 0.226439 0.434946 0.879587 0.058 Uiso 1 1 calc R U . . .
C15 C 0.4100(7) 0.5368(3) 0.8529(4) 0.0679(14) Uani 1 1 d . . . . .
H15A H 0.382325 0.577620 0.901622 0.102 Uiso 1 1 calc R U . . .
H15B H 0.353043 0.559514 0.800820 0.102 Uiso 1 1 calc R U . . .
H15C H 0.531995 0.537017 0.843499 0.102 Uiso 1 1 calc R U . . .
C16 C 0.3294(6) 0.2623(3) 0.8147(3) 0.0478(11) Uani 1 1 d . . . . .
H16A H 0.205007 0.265702 0.817979 0.057 Uiso 1 1 calc R U . . .
H16B H 0.358562 0.224109 0.763518 0.057 Uiso 1 1 calc R U . . .
C17 C 0.3951(5) 0.2121(3) 0.8960(3) 0.0452(9) Uani 1 1 d . . . . .
O17 O 0.5000(4) 0.1497(2) 0.8953(2) 0.0694(9) Uani 1 1 d . . . . .
C18 C 0.3727(7) 0.2012(4) 1.0515(3) 0.0618(13) Uani 1 1 d . . . . .
H18A H 0.347127 0.243996 1.099157 0.093 Uiso 1 1 calc R U . . .
H18B H 0.494062 0.188893 1.050051 0.093 Uiso 1 1 calc R U . . .
H18C H 0.311975 0.142193 1.060059 0.093 Uiso 1 1 calc R U . . .
O18 O 0.3195(4) 0.2443(2) 0.9686(2) 0.0552(8) Uani 1 1 d . . . . .


_geom_special_details            ?

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C13 1.935(3) . ?
O1 C5 1.413(5) . ?
O1 C2 1.424(5) . ?
C2 C3 1.530(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N4 1.469(4) . ?
C3 C6 1.504(6) . ?
C3 H3A 0.9800 . ?
N4 C12 1.351(4) . ?
N4 C5 1.495(5) . ?
C5 C14 1.526(6) . ?
C5 C16 1.539(6) . ?
C6 C11 1.394(6) . ?
C6 C7 1.395(6) . ?
C7 C8 1.378(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.378(7) . ?
C8 H8A 0.9300 . ?
C9 C10 1.370(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.382(6) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 O12 1.226(4) . ?
C12 C13 1.513(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.526(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.509(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O17 1.196(5) . ?
C17 O18 1.328(5) . ?
C18 O18 1.457(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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 O1 C2 109.1(3) . . ?
O1 C2 C3 104.7(3) . . ?
O1 C2 H2A 110.8 . . ?
C3 C2 H2A 110.8 . . ?
O1 C2 H2B 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
N4 C3 C6 116.5(3) . . ?
N4 C3 C2 100.2(3) . . ?
C6 C3 C2 112.2(3) . . ?
N4 C3 H3A 109.2 . . ?
C6 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C12 N4 C3 127.5(3) . . ?
C12 N4 C5 120.6(3) . . ?
C3 N4 C5 110.9(3) . . ?
O1 C5 N4 103.1(3) . . ?
O1 C5 C14 106.7(3) . . ?
N4 C5 C14 112.7(3) . . ?
O1 C5 C16 110.6(3) . . ?
N4 C5 C16 108.3(3) . . ?
C14 C5 C16 114.8(3) . . ?
C11 C6 C7 117.6(4) . . ?
C11 C6 C3 120.6(4) . . ?
C7 C6 C3 121.7(4) . . ?
C8 C7 C6 121.1(4) . . ?
C8 C7 H7A 119.4 . . ?
C6 C7 H7A 119.4 . . ?
C7 C8 C9 120.0(4) . . ?
C7 C8 H8A 120.0 . . ?
C9 C8 H8A 120.0 . . ?
C10 C9 C8 120.1(5) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C9 C10 C11 120.1(4) . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C10 C11 C6 121.1(4) . . ?
C10 C11 H11A 119.5 . . ?
C6 C11 H11A 119.5 . . ?
O12 C12 N4 122.4(4) . . ?
O12 C12 C13 122.5(3) . . ?
N4 C12 C13 115.1(3) . . ?
C12 C13 Br1 110.6(3) . . ?
C12 C13 H13A 109.5 . . ?
Br1 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
Br1 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C5 C14 C15 112.9(4) . . ?
C5 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
C5 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C5 114.6(3) . . ?
C17 C16 H16A 108.6 . . ?
C5 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
C5 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
O17 C17 O18 123.8(4) . . ?
O17 C17 C16 124.4(5) . . ?
O18 C17 C16 111.8(3) . . ?
O18 C18 H18A 109.5 . . ?
O18 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O18 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 O18 C18 116.8(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C2 C3 36.1(4) . . . . ?
O1 C2 C3 N4 -30.7(4) . . . . ?
O1 C2 C3 C6 -154.9(3) . . . . ?
C6 C3 N4 C12 -53.9(5) . . . . ?
C2 C3 N4 C12 -175.1(4) . . . . ?
C6 C3 N4 C5 137.7(3) . . . . ?
C2 C3 N4 C5 16.5(4) . . . . ?
C2 O1 C5 N4 -24.6(4) . . . . ?
C2 O1 C5 C14 -143.6(3) . . . . ?
C2 O1 C5 C16 91.0(4) . . . . ?
C12 N4 C5 O1 -165.7(3) . . . . ?
C3 N4 C5 O1 3.6(4) . . . . ?
C12 N4 C5 C14 -51.1(5) . . . . ?
C3 N4 C5 C14 118.3(3) . . . . ?
C12 N4 C5 C16 77.0(4) . . . . ?
C3 N4 C5 C16 -113.7(4) . . . . ?
N4 C3 C6 C11 135.1(4) . . . . ?
C2 C3 C6 C11 -110.3(4) . . . . ?
N4 C3 C6 C7 -49.4(5) . . . . ?
C2 C3 C6 C7 65.2(4) . . . . ?
C11 C6 C7 C8 0.1(6) . . . . ?
C3 C6 C7 C8 -175.5(4) . . . . ?
C6 C7 C8 C9 -0.3(7) . . . . ?
C7 C8 C9 C10 0.0(7) . . . . ?
C8 C9 C10 C11 0.4(7) . . . . ?
C9 C10 C11 C6 -0.6(7) . . . . ?
C7 C6 C11 C10 0.4(6) . . . . ?
C3 C6 C11 C10 176.0(4) . . . . ?
C3 N4 C12 O12 176.1(4) . . . . ?
C5 N4 C12 O12 -16.5(6) . . . . ?
C3 N4 C12 C13 -4.1(6) . . . . ?
C5 N4 C12 C13 163.3(3) . . . . ?
O12 C12 C13 Br1 14.1(5) . . . . ?
N4 C12 C13 Br1 -165.6(3) . . . . ?
O1 C5 C14 C15 62.2(5) . . . . ?
N4 C5 C14 C15 -50.3(5) . . . . ?
C16 C5 C14 C15 -174.9(4) . . . . ?
O1 C5 C16 C17 57.2(5) . . . . ?
N4 C5 C16 C17 169.5(3) . . . . ?
C14 C5 C16 C17 -63.7(5) . . . . ?
C5 C16 C17 O17 -105.0(5) . . . . ?
C5 C16 C17 O18 76.3(4) . . . . ?
O17 C17 O18 C18 1.3(6) . . . . ?
C16 C17 O18 C18 -180.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2B O12 0.97 2.60 3.504(5) 155.1 1_655 yes
C3 H3A O17 0.98 2.56 3.465(5) 152.7 3_656 yes
C13 H13B O17 0.97 2.51 3.476(5) 176.3 3_656 yes
C14 H14A Br1 0.97 3.02 3.912(4) 153.0 2_565 yes
C14 H14A O18 0.97 2.54 3.050(5) 112.7 . yes
C14 H14B O12 0.97 2.43 2.968(5) 114.5 . yes
C16 H16A O12 0.97 2.54 3.083(5) 115.7 . yes

_refine_diff_density_max         0.500
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_24a
_database_code_depnum_ccdc_archive 'CCDC 2125367'
loop_
_audit_author_name
_audit_author_address
'Sylvain Bernes'
;Instituto de Fisica, BUAP, Puebla
Mexico
;
_audit_update_record             
;
2021-11-30 deposited with the CCDC.	2022-01-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_24a                 
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: The crystal crystallizes in a ncs space group, with Z' = 3 and Z = 12, and is the an intrinsically poorly diffracting sample. Moreover, thickness of the single crystals is limited to 0.07 micras.
;
_vrf_PLAT026_24a                 
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        33% Check
RESPONSE: The crystal crystallizes in a ncs space group, with Z' = 3 and Z = 12, and is the an intrinsically poorly diffracting sample. Moreover, thickness of the single crystals is limited to 0.07 micras.
;
# Added during the CSD deposition process: Tuesday 30 November 2021 08:37 PM
# end Validation Reply Form


# Clave Lab.  :  ENR-410-1
# Clave IF-UAP:  ENR-410-1
# Solicitud: 393
# Firma en la Solicitud: Dr. David Aparicio (ICUAP)
# Clave datos : ... \BUAP\Sylvain\ENR-410-1\70mm_1\

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_audit_creation_date             2019-10-20

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          423
_chemical_formula_moiety         'C17 H21 N O3 S'
_chemical_formula_sum            'C17 H21 N O3 S'
_chemical_formula_weight         319.41
_chemical_absolute_configuration ad
_chemical_optical_rotation       ?

_chemical_properties_physical    ?
_chemical_properties_biological  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.0826 0.0763 '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       ?

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                   5.4670(2)
_cell_length_b                   27.8275(12)
_cell_length_c                   32.842(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4996.4(4)
_cell_formula_units_Z            12
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    12011
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      19.60

_exptl_crystal_recrystallization_method 
;
Re-crystallisation from solvent: AcOEt/benzine
;

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             2040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.458
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.069
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 5 0.0290
2 -1 -9 0.0400
0 0 -1 0.0440
0 0 1 0.0480
1 4 0 0.2520
-2 -9 0 0.2060

_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2503
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'X-AREA 1.86 (Stoe & Cie, 2018)'

_diffrn_ambient_temperature      295(1)
_diffrn_ambient_environment      air
_diffrn_measurement_specimen_support Mitegen
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_diffrn_source_current           0.55
_diffrn_source_power             0.03575
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
1742 frames, 70-100 s/frame, 1 deg./frame, detector distance = 70 mm
;
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            87513
_diffrn_reflns_av_unetI/netI     0.2287
_diffrn_reflns_av_R_equivalents  0.2841
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.271
_diffrn_reflns_theta_max         19.999
_diffrn_reflns_theta_full        19.664
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9490
_reflns_number_gt                3129
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          ?

_computing_data_collection       'X-AREA 1.86 (Stoe & Cie, 2018)'
_computing_cell_refinement       'X-AREA 1.86'
_computing_data_reduction        'X-AREA 1.86'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'

_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)+(0.0114P)²] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00060(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 941 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(15)
_refine_ls_number_reflns         9490
_refine_ls_number_parameters     605
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1652
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0699
_refine_ls_goodness_of_fit_ref   0.647
_refine_ls_restrained_S_all      0.647
_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
S1 S 0.8586(3) 0.52611(7) 0.89092(6) 0.0666(6) Uani 1 1 d . . . . .
N1 N 0.8117(9) 0.63546(19) 0.96566(16) 0.0489(14) Uani 1 1 d . . . . .
C2 C 0.8645(12) 0.5906(3) 0.9493(2) 0.0536(18) Uani 1 1 d . . . . .
O2 O 0.9953(7) 0.56257(17) 0.97014(15) 0.0688(14) Uani 1 1 d . . . . .
C3 C 0.7564(11) 0.5793(2) 0.9116(2) 0.0513(18) Uani 1 1 d . . . . .
C4 C 0.5628(12) 0.6054(3) 0.8940(2) 0.059(2) Uani 1 1 d . . . . .
O4 O 0.4506(9) 0.59342(19) 0.86184(16) 0.0853(16) Uani 1 1 d . . . . .
C5 C 0.4710(11) 0.6481(3) 0.9181(2) 0.064(2) Uani 1 1 d . . . . .
H5A H 0.343508 0.637515 0.936566 0.076 Uiso 1 1 calc R U . . .
H5B H 0.399879 0.671310 0.899516 0.076 Uiso 1 1 calc R U . . .
C6 C 0.6775(12) 0.6724(3) 0.9427(2) 0.0551(18) Uani 1 1 d . . . . .
O6 O 0.5686(9) 0.70005(16) 0.97431(16) 0.0724(14) Uani 1 1 d . . . . .
C7 C 0.7449(13) 0.7000(3) 1.0066(2) 0.077(2) Uani 1 1 d . . . . .
H7A H 0.668340 0.708356 1.032316 0.092 Uiso 1 1 calc R U . . .
H7B H 0.875000 0.722788 1.001101 0.092 Uiso 1 1 calc R U . . .
C8 C 0.8451(12) 0.6484(2) 1.0079(2) 0.0527(18) Uani 1 1 d . . . . .
H8A H 1.019210 0.648476 1.015019 0.063 Uiso 1 1 calc R U . . .
C9 C 0.8454(12) 0.7027(2) 0.9166(2) 0.069(2) Uani 1 1 d . . . . .
H9A H 0.986228 0.711878 0.932744 0.082 Uiso 1 1 calc R U . . .
H9B H 0.904088 0.683028 0.894213 0.082 Uiso 1 1 calc R U . . .
C10 C 0.7325(14) 0.7472(3) 0.8993(3) 0.136(4) Uani 1 1 d . . . . .
H10A H 0.851982 0.764205 0.883450 0.205 Uiso 1 1 calc R U . . .
H10B H 0.676454 0.767363 0.921100 0.205 Uiso 1 1 calc R U . . .
H10C H 0.596697 0.738585 0.882272 0.205 Uiso 1 1 calc R U . . .
C11 C 0.9181(13) 0.5373(3) 0.8386(2) 0.086(2) Uani 1 1 d . . . . .
H11A H 0.959929 0.507744 0.825245 0.128 Uiso 1 1 calc R U . . .
H11B H 1.051625 0.559558 0.836112 0.128 Uiso 1 1 calc R U . . .
H11C H 0.774917 0.550775 0.826039 0.128 Uiso 1 1 calc R U . . .
C12 C 0.5872(10) 0.4888(2) 0.8872(2) 0.075(2) Uani 1 1 d . . . . .
H12A H 0.622898 0.460935 0.871088 0.112 Uiso 1 1 calc R U . . .
H12B H 0.457906 0.506826 0.874585 0.112 Uiso 1 1 calc R U . . .
H12C H 0.537188 0.479068 0.913969 0.112 Uiso 1 1 calc R U . . .
C13 C 0.7011(12) 0.6185(2) 1.0378(2) 0.0514(18) Uani 1 1 d . . . . .
C14 C 0.7686(13) 0.6174(3) 1.0780(2) 0.069(2) Uani 1 1 d . . . . .
H14A H 0.910555 0.633227 1.086007 0.083 Uiso 1 1 calc R U . . .
C15 C 0.6324(16) 0.5937(3) 1.1065(2) 0.083(2) Uani 1 1 d . . . . .
H15A H 0.679982 0.593839 1.133716 0.099 Uiso 1 1 calc R U . . .
C16 C 0.4219(15) 0.5693(3) 1.0946(3) 0.078(2) Uani 1 1 d . . . . .
H16A H 0.329153 0.552792 1.113784 0.094 Uiso 1 1 calc R U . . .
C17 C 0.3507(12) 0.5695(2) 1.0542(3) 0.068(2) Uani 1 1 d . . . . .
H17A H 0.209499 0.553443 1.046165 0.082 Uiso 1 1 calc R U . . .
C18 C 0.4918(12) 0.5938(2) 1.0258(2) 0.0577(19) Uani 1 1 d . . . . .
H18A H 0.446270 0.593558 0.998533 0.069 Uiso 1 1 calc R U . . .
S21 S 0.6737(3) 0.51084(7) 0.72689(6) 0.0606(5) Uani 1 1 d . . . . .
N21 N 0.6676(9) 0.37959(19) 0.77136(17) 0.0495(14) Uani 1 1 d . . . . .
C22 C 0.6261(11) 0.4282(2) 0.7684(2) 0.0475(17) Uani 1 1 d . . . . .
O22 O 0.4822(7) 0.44838(15) 0.79200(13) 0.0582(12) Uani 1 1 d . . . . .
C23 C 0.7674(10) 0.4527(2) 0.7371(2) 0.0512(18) Uani 1 1 d . . . . .
C24 C 0.9719(12) 0.4324(3) 0.7174(2) 0.057(2) Uani 1 1 d . . . . .
O24 O 1.1060(8) 0.45398(17) 0.69195(14) 0.0698(14) Uani 1 1 d . . . . .
C25 C 1.0411(11) 0.3819(2) 0.7306(2) 0.064(2) Uani 1 1 d . . . . .
H25A H 1.151175 0.383689 0.753713 0.077 Uiso 1 1 calc R U . . .
H25B H 1.127023 0.365974 0.708544 0.077 Uiso 1 1 calc R U . . .
C26 C 0.8167(11) 0.3522(2) 0.7423(2) 0.0522(18) Uani 1 1 d . . . . .
O26 O 0.8911(7) 0.31181(15) 0.76637(14) 0.0613(13) Uani 1 1 d . . . . .
C27 C 0.6874(11) 0.3008(2) 0.7924(2) 0.060(2) Uani 1 1 d . . . . .
H27A H 0.736678 0.280609 0.815015 0.072 Uiso 1 1 calc R U . . .
H27B H 0.557202 0.285062 0.777446 0.072 Uiso 1 1 calc R U . . .
C28 C 0.6071(11) 0.3516(2) 0.80735(19) 0.0490(17) Uani 1 1 d . . . . .
H28A H 0.430027 0.352140 0.811989 0.059 Uiso 1 1 calc R U . . .
C29 C 0.6611(12) 0.3355(3) 0.70623(19) 0.068(2) Uani 1 1 d . . . . .
H29A H 0.514193 0.320189 0.716550 0.081 Uiso 1 1 calc R U . . .
H29B H 0.611499 0.363306 0.690498 0.081 Uiso 1 1 calc R U . . .
C30 C 0.7932(14) 0.3005(3) 0.6783(2) 0.103(3) Uani 1 1 d . . . . .
H30A H 0.683337 0.289717 0.657446 0.155 Uiso 1 1 calc R U . . .
H30B H 0.848907 0.273389 0.693880 0.155 Uiso 1 1 calc R U . . .
H30C H 0.930964 0.316240 0.666067 0.155 Uiso 1 1 calc R U . . .
C31 C 0.6143(12) 0.5135(3) 0.67307(18) 0.073(2) Uani 1 1 d . . . . .
H31A H 0.589445 0.546322 0.665085 0.110 Uiso 1 1 calc R U . . .
H31B H 0.470443 0.495111 0.666906 0.110 Uiso 1 1 calc R U . . .
H31C H 0.751393 0.500484 0.658506 0.110 Uiso 1 1 calc R U . . .
C32 C 0.9452(10) 0.5468(2) 0.7299(2) 0.074(2) Uani 1 1 d . . . . .
H32A H 0.927132 0.574659 0.712937 0.111 Uiso 1 1 calc R U . . .
H32B H 1.083054 0.528320 0.720890 0.111 Uiso 1 1 calc R U . . .
H32C H 0.970604 0.556739 0.757609 0.111 Uiso 1 1 calc R U . . .
C33 C 0.7397(11) 0.3658(2) 0.8456(2) 0.0480(17) Uani 1 1 d . . . . .
C34 C 0.6595(12) 0.3496(2) 0.8831(2) 0.0604(19) Uani 1 1 d . . . . .
H34A H 0.518112 0.331124 0.884345 0.072 Uiso 1 1 calc R U . . .
C35 C 0.7824(13) 0.3601(3) 0.9186(2) 0.066(2) Uani 1 1 d . . . . .
H35A H 0.723731 0.348993 0.943451 0.079 Uiso 1 1 calc R U . . .
C36 C 0.9940(13) 0.3873(3) 0.9170(3) 0.072(2) Uani 1 1 d . . . . .
H36A H 1.077198 0.395023 0.940801 0.086 Uiso 1 1 calc R U . . .
C37 C 1.0805(13) 0.4029(3) 0.8800(3) 0.073(2) Uani 1 1 d . . . . .
H37A H 1.224287 0.420750 0.878970 0.088 Uiso 1 1 calc R U . . .
C38 C 0.9580(11) 0.3927(2) 0.8446(2) 0.0538(18) Uani 1 1 d . . . . .
H38A H 1.019209 0.403489 0.819839 0.065 Uiso 1 1 calc R U . . .
S41 S 1.0891(3) 0.05503(7) 0.93908(6) 0.0615(5) Uani 1 1 d . . . . .
N41 N 1.1370(9) 0.1758(2) 0.87795(17) 0.0517(14) Uani 1 1 d . . . . .
C42 C 1.0811(11) 0.1288(3) 0.8865(2) 0.0497(17) Uani 1 1 d . . . . .
O42 O 0.9400(7) 0.10576(16) 0.86381(13) 0.0614(13) Uani 1 1 d . . . . .
C43 C 1.1979(11) 0.1103(2) 0.9227(2) 0.0547(19) Uani 1 1 d . . . . .
C44 C 1.3972(12) 0.1334(3) 0.9432(2) 0.0595(19) Uani 1 1 d . . . . .
O44 O 1.4988(8) 0.11687(17) 0.97447(15) 0.0701(15) Uani 1 1 d . . . . .
C45 C 1.4883(10) 0.1788(2) 0.9236(2) 0.058(2) Uani 1 1 d . . . . .
H45A H 1.605308 0.170835 0.902457 0.070 Uiso 1 1 calc R U . . .
H45B H 1.571364 0.198324 0.943803 0.070 Uiso 1 1 calc R U . . .
C46 C 1.2804(11) 0.2073(3) 0.9053(2) 0.0519(18) Uani 1 1 d . . . . .
O46 O 1.3711(7) 0.24233(16) 0.87747(13) 0.0580(12) Uani 1 1 d . . . . .
C47 C 1.1760(12) 0.2498(2) 0.8490(2) 0.065(2) Uani 1 1 d . . . . .
H47A H 1.235446 0.265795 0.824711 0.078 Uiso 1 1 calc R U . . .
H47B H 1.047627 0.269256 0.861067 0.078 Uiso 1 1 calc R U . . .
C48 C 1.0825(11) 0.2000(2) 0.8391(2) 0.0528(18) Uani 1 1 d . . . . .
H48A H 0.905572 0.200732 0.834330 0.063 Uiso 1 1 calc R U . . .
C49 C 1.1165(11) 0.2311(2) 0.9372(2) 0.0587(19) Uani 1 1 d . . . . .
H49A H 0.974832 0.244910 0.923835 0.070 Uiso 1 1 calc R U . . .
H49B H 1.058990 0.206889 0.956170 0.070 Uiso 1 1 calc R U . . .
C50 C 1.2495(12) 0.2704(3) 0.9608(2) 0.076(2) Uani 1 1 d . . . . .
H50A H 1.131853 0.291253 0.973488 0.114 Uiso 1 1 calc R U . . .
H50B H 1.349552 0.288753 0.942492 0.114 Uiso 1 1 calc R U . . .
H50C H 1.350780 0.256081 0.981377 0.114 Uiso 1 1 calc R U . . .
C51 C 1.0124(12) 0.0607(3) 0.9918(2) 0.083(2) Uani 1 1 d . . . . .
H51A H 0.953783 0.030365 1.001776 0.124 Uiso 1 1 calc R U . . .
H51B H 0.887186 0.084561 0.994931 0.124 Uiso 1 1 calc R U . . .
H51C H 1.154886 0.070075 1.006850 0.124 Uiso 1 1 calc R U . . .
C52 C 1.3549(10) 0.0172(2) 0.9426(2) 0.072(2) Uani 1 1 d . . . . .
H52A H 1.308039 -0.013840 0.952605 0.108 Uiso 1 1 calc R U . . .
H52B H 1.471113 0.031465 0.960854 0.108 Uiso 1 1 calc R U . . .
H52C H 1.427420 0.013859 0.916099 0.108 Uiso 1 1 calc R U . . .
C53 C 1.2112(12) 0.1791(2) 0.8029(2) 0.0505(18) Uani 1 1 d . . . . .
C54 C 1.1237(14) 0.1892(3) 0.7645(2) 0.073(2) Uani 1 1 d . . . . .
H54A H 0.980629 0.207043 0.761859 0.088 Uiso 1 1 calc R U . . .
C55 C 1.2432(18) 0.1736(3) 0.7293(3) 0.102(3) Uani 1 1 d . . . . .
H55A H 1.182331 0.180870 0.703595 0.123 Uiso 1 1 calc R U . . .
C56 C 1.4578(18) 0.1465(3) 0.7340(3) 0.095(3) Uani 1 1 d . . . . .
H56A H 1.540051 0.135220 0.711116 0.114 Uiso 1 1 calc R U . . .
C57 C 1.5446(15) 0.1369(3) 0.7711(3) 0.088(3) Uani 1 1 d . . . . .
H57A H 1.689077 0.119490 0.773450 0.105 Uiso 1 1 calc R U . . .
C58 C 1.4258(12) 0.1522(3) 0.8067(2) 0.064(2) Uani 1 1 d . . . . .
H58A H 1.488342 0.144501 0.832197 0.077 Uiso 1 1 calc R U . . .


_geom_special_details            ?

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
S1 C3 1.721(7) . ?
S1 C11 1.778(7) . ?
S1 C12 1.814(6) . ?
N1 C2 1.388(8) . ?
N1 C8 1.445(7) . ?
N1 C6 1.471(8) . ?
C2 O2 1.260(7) . ?
C2 C3 1.409(8) . ?
C3 C4 1.407(8) . ?
C4 O4 1.267(7) . ?
C4 C5 1.511(9) . ?
C5 C6 1.546(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O6 1.421(7) . ?
C6 C9 1.513(8) . ?
O6 C7 1.433(7) . ?
C7 C8 1.537(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C13 1.509(9) . ?
C8 H8A 0.9800 . ?
C9 C10 1.495(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.370(9) . ?
C13 C18 1.393(8) . ?
C14 C15 1.368(9) . ?
C14 H14A 0.9300 . ?
C15 C16 1.393(10) . ?
C15 H15A 0.9300 . ?
C16 C17 1.381(9) . ?
C16 H16A 0.9300 . ?
C17 C18 1.387(8) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
S21 C23 1.729(6) . ?
S21 C32 1.793(6) . ?
S21 C31 1.799(6) . ?
N21 C22 1.375(7) . ?
N21 C28 1.454(7) . ?
N21 C26 1.469(7) . ?
C22 O22 1.240(7) . ?
C22 C23 1.454(8) . ?
C23 C24 1.411(8) . ?
C24 O24 1.263(7) . ?
C24 C25 1.519(9) . ?
C25 C26 1.527(8) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 O26 1.435(7) . ?
C26 C29 1.530(8) . ?
O26 C27 1.437(7) . ?
C27 C28 1.557(8) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C33 1.504(8) . ?
C28 H28A 0.9800 . ?
C29 C30 1.519(9) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.380(8) . ?
C33 C38 1.409(8) . ?
C34 C35 1.378(8) . ?
C34 H34A 0.9300 . ?
C35 C36 1.383(9) . ?
C35 H35A 0.9300 . ?
C36 C37 1.373(9) . ?
C36 H36A 0.9300 . ?
C37 C38 1.372(8) . ?
C37 H37A 0.9300 . ?
C38 H38A 0.9300 . ?
S41 C43 1.735(7) . ?
S41 C51 1.787(7) . ?
S41 C52 1.798(6) . ?
N41 C42 1.372(7) . ?
N41 C48 1.473(7) . ?
N41 C46 1.479(8) . ?
C42 O42 1.250(7) . ?
C42 C43 1.445(8) . ?
C43 C44 1.432(9) . ?
C44 O44 1.256(8) . ?
C44 C45 1.503(8) . ?
C45 C46 1.510(8) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 O46 1.425(7) . ?
C46 C49 1.531(8) . ?
O46 C47 1.433(7) . ?
C47 C48 1.515(8) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C48 C53 1.497(8) . ?
C48 H48A 0.9800 . ?
C49 C50 1.525(8) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C53 C54 1.380(9) . ?
C53 C58 1.398(8) . ?
C54 C55 1.396(10) . ?
C54 H54A 0.9300 . ?
C55 C56 1.403(10) . ?
C55 H55A 0.9300 . ?
C56 C57 1.335(10) . ?
C56 H56A 0.9300 . ?
C57 C58 1.402(9) . ?
C57 H57A 0.9300 . ?
C58 H58A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C11 106.8(4) . . ?
C3 S1 C12 104.6(3) . . ?
C11 S1 C12 100.7(3) . . ?
C2 N1 C8 124.7(6) . . ?
C2 N1 C6 122.3(6) . . ?
C8 N1 C6 112.3(5) . . ?
O2 C2 N1 117.7(6) . . ?
O2 C2 C3 125.2(7) . . ?
N1 C2 C3 117.0(6) . . ?
C4 C3 C2 124.1(7) . . ?
C4 C3 S1 121.8(5) . . ?
C2 C3 S1 113.8(5) . . ?
O4 C4 C3 124.7(7) . . ?
O4 C4 C5 118.8(6) . . ?
C3 C4 C5 116.2(6) . . ?
C4 C5 C6 112.1(6) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
O6 C6 N1 102.3(5) . . ?
O6 C6 C9 111.6(6) . . ?
N1 C6 C9 112.2(5) . . ?
O6 C6 C5 108.3(5) . . ?
N1 C6 C5 109.0(6) . . ?
C9 C6 C5 112.9(6) . . ?
C6 O6 C7 105.0(5) . . ?
O6 C7 C8 105.1(6) . . ?
O6 C7 H7A 110.7 . . ?
C8 C7 H7A 110.7 . . ?
O6 C7 H7B 110.7 . . ?
C8 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
N1 C8 C13 114.9(6) . . ?
N1 C8 C7 99.3(5) . . ?
C13 C8 C7 110.3(5) . . ?
N1 C8 H8A 110.6 . . ?
C13 C8 H8A 110.6 . . ?
C7 C8 H8A 110.6 . . ?
C10 C9 C6 115.2(6) . . ?
C10 C9 H9A 108.5 . . ?
C6 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C6 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 118.9(7) . . ?
C14 C13 C8 119.9(7) . . ?
C18 C13 C8 121.1(7) . . ?
C15 C14 C13 121.6(7) . . ?
C15 C14 H14A 119.2 . . ?
C13 C14 H14A 119.2 . . ?
C14 C15 C16 119.5(7) . . ?
C14 C15 H15A 120.3 . . ?
C16 C15 H15A 120.3 . . ?
C17 C16 C15 120.1(8) . . ?
C17 C16 H16A 120.0 . . ?
C15 C16 H16A 120.0 . . ?
C16 C17 C18 119.4(7) . . ?
C16 C17 H17A 120.3 . . ?
C18 C17 H17A 120.3 . . ?
C17 C18 C13 120.5(7) . . ?
C17 C18 H18A 119.7 . . ?
C13 C18 H18A 119.7 . . ?
C23 S21 C32 105.4(3) . . ?
C23 S21 C31 106.4(3) . . ?
C32 S21 C31 100.4(3) . . ?
C22 N21 C28 123.2(6) . . ?
C22 N21 C26 123.7(6) . . ?
C28 N21 C26 112.2(5) . . ?
O22 C22 N21 120.4(6) . . ?
O22 C22 C23 124.5(6) . . ?
N21 C22 C23 115.2(6) . . ?
C24 C23 C22 123.8(6) . . ?
C24 C23 S21 121.3(5) . . ?
C22 C23 S21 114.8(5) . . ?
O24 C24 C23 125.0(7) . . ?
O24 C24 C25 118.9(6) . . ?
C23 C24 C25 115.9(7) . . ?
C24 C25 C26 111.8(5) . . ?
C24 C25 H25A 109.3 . . ?
C26 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
C26 C25 H25B 109.3 . . ?
H25A C25 H25B 107.9 . . ?
O26 C26 N21 101.8(5) . . ?
O26 C26 C25 109.5(5) . . ?
N21 C26 C25 109.2(5) . . ?
O26 C26 C29 110.2(5) . . ?
N21 C26 C29 110.6(5) . . ?
C25 C26 C29 114.7(6) . . ?
C26 O26 C27 106.0(4) . . ?
O26 C27 C28 102.3(5) . . ?
O26 C27 H27A 111.3 . . ?
C28 C27 H27A 111.3 . . ?
O26 C27 H27B 111.3 . . ?
C28 C27 H27B 111.3 . . ?
H27A C27 H27B 109.2 . . ?
N21 C28 C33 115.4(5) . . ?
N21 C28 C27 99.5(5) . . ?
C33 C28 C27 111.4(5) . . ?
N21 C28 H28A 110.0 . . ?
C33 C28 H28A 110.0 . . ?
C27 C28 H28A 110.0 . . ?
C30 C29 C26 113.4(6) . . ?
C30 C29 H29A 108.9 . . ?
C26 C29 H29A 108.9 . . ?
C30 C29 H29B 108.9 . . ?
C26 C29 H29B 108.9 . . ?
H29A C29 H29B 107.7 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
S21 C31 H31A 109.5 . . ?
S21 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
S21 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
S21 C32 H32A 109.5 . . ?
S21 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
S21 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 C38 117.6(7) . . ?
C34 C33 C28 120.4(6) . . ?
C38 C33 C28 121.8(7) . . ?
C35 C34 C33 122.1(7) . . ?
C35 C34 H34A 119.0 . . ?
C33 C34 H34A 119.0 . . ?
C34 C35 C36 119.4(8) . . ?
C34 C35 H35A 120.3 . . ?
C36 C35 H35A 120.3 . . ?
C37 C36 C35 119.7(7) . . ?
C37 C36 H36A 120.2 . . ?
C35 C36 H36A 120.2 . . ?
C38 C37 C36 121.0(7) . . ?
C38 C37 H37A 119.5 . . ?
C36 C37 H37A 119.5 . . ?
C37 C38 C33 120.3(7) . . ?
C37 C38 H38A 119.9 . . ?
C33 C38 H38A 119.9 . . ?
C43 S41 C51 107.6(3) . . ?
C43 S41 C52 105.2(3) . . ?
C51 S41 C52 100.3(3) . . ?
C42 N41 C48 124.5(6) . . ?
C42 N41 C46 123.9(6) . . ?
C48 N41 C46 111.3(5) . . ?
O42 C42 N41 120.3(6) . . ?
O42 C42 C43 125.5(6) . . ?
N41 C42 C43 114.2(6) . . ?
C44 C43 C42 124.2(6) . . ?
C44 C43 S41 120.9(5) . . ?
C42 C43 S41 114.8(5) . . ?
O44 C44 C43 123.7(7) . . ?
O44 C44 C45 120.8(6) . . ?
C43 C44 C45 115.4(7) . . ?
C44 C45 C46 111.2(5) . . ?
C44 C45 H45A 109.4 . . ?
C46 C45 H45A 109.4 . . ?
C44 C45 H45B 109.4 . . ?
C46 C45 H45B 109.4 . . ?
H45A C45 H45B 108.0 . . ?
O46 C46 N41 101.6(5) . . ?
O46 C46 C45 110.6(5) . . ?
N41 C46 C45 109.3(6) . . ?
O46 C46 C49 110.3(6) . . ?
N41 C46 C49 111.2(5) . . ?
C45 C46 C49 113.3(6) . . ?
C46 O46 C47 105.0(5) . . ?
O46 C47 C48 105.0(5) . . ?
O46 C47 H47A 110.8 . . ?
C48 C47 H47A 110.8 . . ?
O46 C47 H47B 110.8 . . ?
C48 C47 H47B 110.8 . . ?
H47A C47 H47B 108.8 . . ?
N41 C48 C53 114.6(5) . . ?
N41 C48 C47 99.3(5) . . ?
C53 C48 C47 111.6(5) . . ?
N41 C48 H48A 110.3 . . ?
C53 C48 H48A 110.3 . . ?
C47 C48 H48A 110.3 . . ?
C50 C49 C46 112.4(5) . . ?
C50 C49 H49A 109.1 . . ?
C46 C49 H49A 109.1 . . ?
C50 C49 H49B 109.1 . . ?
C46 C49 H49B 109.1 . . ?
H49A C49 H49B 107.9 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
S41 C51 H51A 109.5 . . ?
S41 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
S41 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
S41 C52 H52A 109.5 . . ?
S41 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
S41 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C54 C53 C58 118.8(7) . . ?
C54 C53 C48 119.0(7) . . ?
C58 C53 C48 122.2(7) . . ?
C53 C54 C55 122.1(8) . . ?
C53 C54 H54A 119.0 . . ?
C55 C54 H54A 119.0 . . ?
C54 C55 C56 117.9(9) . . ?
C54 C55 H55A 121.0 . . ?
C56 C55 H55A 121.0 . . ?
C57 C56 C55 120.3(10) . . ?
C57 C56 H56A 119.8 . . ?
C55 C56 H56A 119.8 . . ?
C56 C57 C58 122.4(8) . . ?
C56 C57 H57A 118.8 . . ?
C58 C57 H57A 118.8 . . ?
C53 C58 C57 118.5(7) . . ?
C53 C58 H58A 120.7 . . ?
C57 C58 H58A 120.7 . . ?

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
C8 N1 C2 O2 -15.2(9) . . . . ?
C6 N1 C2 O2 175.0(5) . . . . ?
C8 N1 C2 C3 161.6(6) . . . . ?
C6 N1 C2 C3 -8.1(9) . . . . ?
O2 C2 C3 C4 162.6(6) . . . . ?
N1 C2 C3 C4 -13.9(9) . . . . ?
O2 C2 C3 S1 -10.4(9) . . . . ?
N1 C2 C3 S1 173.1(5) . . . . ?
C11 S1 C3 C4 51.9(6) . . . . ?
C12 S1 C3 C4 -54.3(6) . . . . ?
C11 S1 C3 C2 -134.9(5) . . . . ?
C12 S1 C3 C2 118.9(5) . . . . ?
C2 C3 C4 O4 -173.9(7) . . . . ?
S1 C3 C4 O4 -1.4(10) . . . . ?
C2 C3 C4 C5 0.2(9) . . . . ?
S1 C3 C4 C5 172.6(5) . . . . ?
O4 C4 C5 C6 -153.3(6) . . . . ?
C3 C4 C5 C6 32.3(8) . . . . ?
C2 N1 C6 O6 153.8(5) . . . . ?
C8 N1 C6 O6 -17.1(7) . . . . ?
C2 N1 C6 C9 -86.5(7) . . . . ?
C8 N1 C6 C9 102.6(7) . . . . ?
C2 N1 C6 C5 39.2(8) . . . . ?
C8 N1 C6 C5 -131.7(5) . . . . ?
C4 C5 C6 O6 -160.0(5) . . . . ?
C4 C5 C6 N1 -49.4(7) . . . . ?
C4 C5 C6 C9 75.9(7) . . . . ?
N1 C6 O6 C7 35.3(6) . . . . ?
C9 C6 O6 C7 -84.8(6) . . . . ?
C5 C6 O6 C7 150.4(5) . . . . ?
C6 O6 C7 C8 -41.2(7) . . . . ?
C2 N1 C8 C13 -59.8(8) . . . . ?
C6 N1 C8 C13 110.8(6) . . . . ?
C2 N1 C8 C7 -177.4(6) . . . . ?
C6 N1 C8 C7 -6.8(7) . . . . ?
O6 C7 C8 N1 28.4(6) . . . . ?
O6 C7 C8 C13 -92.6(7) . . . . ?
O6 C6 C9 C10 -53.5(9) . . . . ?
N1 C6 C9 C10 -167.6(7) . . . . ?
C5 C6 C9 C10 68.8(9) . . . . ?
N1 C8 C13 C14 160.8(6) . . . . ?
C7 C8 C13 C14 -87.9(8) . . . . ?
N1 C8 C13 C18 -22.5(9) . . . . ?
C7 C8 C13 C18 88.7(8) . . . . ?
C18 C13 C14 C15 -1.7(11) . . . . ?
C8 C13 C14 C15 175.1(7) . . . . ?
C13 C14 C15 C16 1.1(12) . . . . ?
C14 C15 C16 C17 -0.6(11) . . . . ?
C15 C16 C17 C18 0.6(11) . . . . ?
C16 C17 C18 C13 -1.1(10) . . . . ?
C14 C13 C18 C17 1.7(10) . . . . ?
C8 C13 C18 C17 -175.0(6) . . . . ?
C28 N21 C22 O22 -17.7(9) . . . . ?
C26 N21 C22 O22 174.0(5) . . . . ?
C28 N21 C22 C23 160.3(5) . . . . ?
C26 N21 C22 C23 -7.9(9) . . . . ?
O22 C22 C23 C24 163.7(6) . . . . ?
N21 C22 C23 C24 -14.3(9) . . . . ?
O22 C22 C23 S21 -13.8(8) . . . . ?
N21 C22 C23 S21 168.2(4) . . . . ?
C32 S21 C23 C24 -48.6(6) . . . . ?
C31 S21 C23 C24 57.6(6) . . . . ?
C32 S21 C23 C22 129.0(5) . . . . ?
C31 S21 C23 C22 -124.9(5) . . . . ?
C22 C23 C24 O24 -175.6(6) . . . . ?
S21 C23 C24 O24 1.7(9) . . . . ?
C22 C23 C24 C25 0.0(9) . . . . ?
S21 C23 C24 C25 177.4(5) . . . . ?
O24 C24 C25 C26 -150.8(6) . . . . ?
C23 C24 C25 C26 33.3(8) . . . . ?
C22 N21 C26 O26 156.0(5) . . . . ?
C28 N21 C26 O26 -13.4(6) . . . . ?
C22 N21 C26 C25 40.2(8) . . . . ?
C28 N21 C26 C25 -129.1(5) . . . . ?
C22 N21 C26 C29 -86.9(7) . . . . ?
C28 N21 C26 C29 103.7(6) . . . . ?
C24 C25 C26 O26 -161.5(5) . . . . ?
C24 C25 C26 N21 -50.8(8) . . . . ?
C24 C25 C26 C29 74.1(8) . . . . ?
N21 C26 O26 C27 35.7(6) . . . . ?
C25 C26 O26 C27 151.3(6) . . . . ?
C29 C26 O26 C27 -81.7(6) . . . . ?
C26 O26 C27 C28 -44.0(6) . . . . ?
C22 N21 C28 C33 -62.0(8) . . . . ?
C26 N21 C28 C33 107.4(6) . . . . ?
C22 N21 C28 C27 178.6(5) . . . . ?
C26 N21 C28 C27 -11.9(6) . . . . ?
O26 C27 C28 N21 32.9(6) . . . . ?
O26 C27 C28 C33 -89.4(6) . . . . ?
O26 C26 C29 C30 -59.1(8) . . . . ?
N21 C26 C29 C30 -171.0(6) . . . . ?
C25 C26 C29 C30 65.0(8) . . . . ?
N21 C28 C33 C34 165.3(6) . . . . ?
C27 C28 C33 C34 -82.2(7) . . . . ?
N21 C28 C33 C38 -19.5(8) . . . . ?
C27 C28 C33 C38 93.1(7) . . . . ?
C38 C33 C34 C35 1.6(9) . . . . ?
C28 C33 C34 C35 177.1(6) . . . . ?
C33 C34 C35 C36 -0.5(10) . . . . ?
C34 C35 C36 C37 -0.9(11) . . . . ?
C35 C36 C37 C38 1.1(11) . . . . ?
C36 C37 C38 C33 0.0(10) . . . . ?
C34 C33 C38 C37 -1.4(9) . . . . ?
C28 C33 C38 C37 -176.8(6) . . . . ?
C48 N41 C42 O42 -12.7(9) . . . . ?
C46 N41 C42 O42 173.3(5) . . . . ?
C48 N41 C42 C43 167.3(5) . . . . ?
C46 N41 C42 C43 -6.7(9) . . . . ?
O42 C42 C43 C44 165.9(6) . . . . ?
N41 C42 C43 C44 -14.1(9) . . . . ?
O42 C42 C43 S41 -10.9(8) . . . . ?
N41 C42 C43 S41 169.2(5) . . . . ?
C51 S41 C43 C44 54.9(6) . . . . ?
C52 S41 C43 C44 -51.4(6) . . . . ?
C51 S41 C43 C42 -128.2(5) . . . . ?
C52 S41 C43 C42 125.5(5) . . . . ?
C42 C43 C44 O44 -179.4(7) . . . . ?
S41 C43 C44 O44 -2.8(9) . . . . ?
C42 C43 C44 C45 -2.1(9) . . . . ?
S41 C43 C44 C45 174.5(5) . . . . ?
O44 C44 C45 C46 -146.3(6) . . . . ?
C43 C44 C45 C46 36.3(8) . . . . ?
C42 N41 C46 O46 157.1(5) . . . . ?
C48 N41 C46 O46 -17.6(6) . . . . ?
C42 N41 C46 C45 40.2(8) . . . . ?
C48 N41 C46 C45 -134.5(5) . . . . ?
C42 N41 C46 C49 -85.6(7) . . . . ?
C48 N41 C46 C49 99.7(6) . . . . ?
C44 C45 C46 O46 -163.7(5) . . . . ?
C44 C45 C46 N41 -52.7(7) . . . . ?
C44 C45 C46 C49 71.9(8) . . . . ?
N41 C46 O46 C47 37.0(6) . . . . ?
C45 C46 O46 C47 152.9(5) . . . . ?
C49 C46 O46 C47 -81.0(6) . . . . ?
C46 O46 C47 C48 -43.9(6) . . . . ?
C42 N41 C48 C53 -63.2(8) . . . . ?
C46 N41 C48 C53 111.5(6) . . . . ?
C42 N41 C48 C47 177.8(6) . . . . ?
C46 N41 C48 C47 -7.5(6) . . . . ?
O46 C47 C48 N41 30.2(6) . . . . ?
O46 C47 C48 C53 -91.0(6) . . . . ?
O46 C46 C49 C50 -57.8(7) . . . . ?
N41 C46 C49 C50 -169.7(6) . . . . ?
C45 C46 C49 C50 66.8(8) . . . . ?
N41 C48 C53 C54 161.6(6) . . . . ?
C47 C48 C53 C54 -86.5(7) . . . . ?
N41 C48 C53 C58 -22.3(9) . . . . ?
C47 C48 C53 C58 89.6(7) . . . . ?
C58 C53 C54 C55 -0.3(11) . . . . ?
C48 C53 C54 C55 175.9(7) . . . . ?
C53 C54 C55 C56 0.4(12) . . . . ?
C54 C55 C56 C57 -0.9(13) . . . . ?
C55 C56 C57 C58 1.3(13) . . . . ?
C54 C53 C58 C57 0.7(10) . . . . ?
C48 C53 C58 C57 -175.4(6) . . . . ?
C56 C57 C58 C53 -1.2(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7B O6 0.97 2.53 3.356(8) 143.4 4_567 yes
C11 H11B O4 0.96 2.52 3.391(8) 150.5 1_655 yes
C11 H11C O4 0.96 2.44 3.090(8) 125.2 . yes
C12 H12B O4 0.96 2.45 3.118(8) 126.8 . yes
C31 H31B O24 0.96 2.44 3.294(8) 148.0 1_455 yes
C31 H31C O24 0.96 2.58 3.217(8) 124.4 . yes
C32 H32B O24 0.96 2.28 3.001(8) 131.2 . yes
C51 H51B O44 0.96 2.40 3.264(8) 149.2 1_455 yes
C51 H51C O44 0.96 2.52 3.137(8) 121.9 . yes
C52 H52B O44 0.96 2.42 3.067(8) 124.2 . yes

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_22ab
_database_code_depnum_ccdc_archive 'CCDC 2125365'
loop_
_audit_author_name
_audit_author_address
'Sylvain Bernes'
;Instituto de Fisica, BUAP, Puebla
Mexico
;
_audit_update_record             
;
2021-11-30 deposited with the CCDC.	2022-01-21 downloaded from the CCDC.
;

# Clave Lab.  :  ENR-101
# Clave IF-UAP:  ENR101
# Solicitud: 97
# Firma en la Solicitud: Dr. Joel L. Teran, ICUAP
# Clave datos : ... \BUAP\Sylvain\ENR101\40mm_2\

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_audit_creation_date             2018-04-18

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 N O3 S'
_chemical_formula_sum            'C15 H17 N O3 S'
_chemical_formula_weight         291.35
_chemical_absolute_configuration ad
_chemical_optical_rotation       ?

_chemical_properties_physical    ?
_chemical_properties_biological  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.0826 0.0763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       ?

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.0976(4)
_cell_length_b                   9.5728(8)
_cell_length_c                   12.3463(10)
_cell_angle_alpha                99.389(7)
_cell_angle_beta                 90.433(6)
_cell_angle_gamma                89.796(7)
_cell_volume                     710.99(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    243(1)
_cell_measurement_reflns_used    10706
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      26.73

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5109
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2015)'

_diffrn_ambient_temperature      243(1)
_diffrn_ambient_environment      air
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_diffrn_source_current           0.600
_diffrn_source_power             0.039
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
1375 frames, 115 s/frame, 1 deg./frame, detector distance = 40 mm
;
_diffrn_detector_area_resol_mean 5.81

_diffrn_reflns_number            17365
_diffrn_reflns_av_unetI/netI     0.1109
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.636
_diffrn_reflns_theta_max         19.999
_diffrn_reflns_theta_full        19.664
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.890
_reflns_number_total             4804
_reflns_number_gt                2713
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_max     0.785
_reflns_Friedel_fraction_full    0.783

_reflns_special_details          ?

_computing_data_collection       'X-AREA (Stoe & Cie, 2015)'
_computing_cell_refinement       X-AREA
_computing_data_reduction        X-AREA
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'

_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)+(0.0511P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 782 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.20(16)
_refine_ls_number_reflns         4804
_refine_ls_number_parameters     375
_refine_ls_number_restraints     3
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1234
_refine_ls_wR_factor_gt          0.1105
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_restrained_S_all      0.900
_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
S1 S 0.2728(3) 0.0994(2) 0.49990(16) 0.0589(6) Uani 1 1 d . . . . .
O1 O -0.2041(10) 0.1155(7) 0.9067(5) 0.094(2) Uani 1 1 d . . . . .
O2 O -0.1218(7) 0.2781(5) 0.5896(4) 0.0491(12) Uani 1 1 d . . . . .
O3 O 0.3854(10) -0.0611(6) 0.6757(5) 0.0852(19) Uani 1 1 d . . . . .
C2 C -0.3647(15) 0.2057(10) 0.8955(7) 0.076(3) Uani 1 1 d . . . . .
H2A H -0.365769 0.281447 0.959287 0.091 Uiso 1 1 calc R U . . .
H2B H -0.505724 0.156396 0.892495 0.091 Uiso 1 1 calc R U . . .
C3 C -0.3357(11) 0.2706(7) 0.7898(6) 0.0453(17) Uani 1 1 d . . . . .
H3A H -0.452370 0.236147 0.735966 0.054 Uiso 1 1 calc R U . . .
N4 N -0.1270(9) 0.2053(7) 0.7545(5) 0.0544(17) Uani 1 1 d . . . . .
C5 C -0.0443(10) 0.2021(7) 0.6509(6) 0.0413(16) Uani 1 1 d . . . . .
C6 C 0.1372(11) 0.1071(8) 0.6239(6) 0.0437(18) Uani 1 1 d . . . . .
C7 C 0.2211(13) 0.0152(8) 0.6943(6) 0.058(2) Uani 1 1 d . . . . .
C8 C 0.0919(17) 0.0164(10) 0.7994(7) 0.086(3) Uani 1 1 d . . . . .
H8A H -0.014677 -0.061038 0.786715 0.104 Uiso 0.55(3) 1 calc R U P A 1
H8B H 0.193701 -0.003968 0.856655 0.104 Uiso 0.55(3) 1 calc R U P A 1
H8C H 0.094497 -0.079553 0.817469 0.104 Uiso 0.45(3) 1 calc R U P A 2
H8D H 0.168253 0.078167 0.858863 0.104 Uiso 0.45(3) 1 calc R U P A 2
C8AA C -0.021(4) 0.142(3) 0.8398(17) 0.071(9) Uani 0.55(3) 1 d . . P A 1
H8AA H 0.079782 0.210981 0.882692 0.085 Uiso 0.55(3) 1 calc R U P A 1
C8AB C -0.123(3) 0.060(2) 0.7980(16) 0.035(6) Uani 0.45(3) 1 d . . P A 2
H8AB H -0.220452 -0.011976 0.756010 0.043 Uiso 0.45(3) 1 calc R U P A 2
C9 C -0.3335(10) 0.4299(7) 0.8115(5) 0.0390(16) Uani 1 1 d . . . . .
C10 C -0.5180(12) 0.5033(9) 0.7833(6) 0.0552(19) Uani 1 1 d . . . . .
H10A H -0.636568 0.451789 0.747987 0.066 Uiso 1 1 calc R U . . .
C11 C -0.5314(17) 0.6457(11) 0.8051(8) 0.073(3) Uani 1 1 d . . . . .
H11A H -0.657280 0.692437 0.784649 0.087 Uiso 1 1 calc R U . . .
C12 C -0.362(2) 0.7213(11) 0.8568(9) 0.090(3) Uani 1 1 d . . . . .
H12A H -0.371240 0.820574 0.872623 0.108 Uiso 1 1 calc R U . . .
C13 C -0.1789(18) 0.6555(12) 0.8858(7) 0.075(3) Uani 1 1 d . . . . .
H13A H -0.062482 0.709312 0.921004 0.090 Uiso 1 1 calc R U . . .
C14 C -0.1619(12) 0.5077(10) 0.8636(6) 0.058(2) Uani 1 1 d . . . . .
H14A H -0.035073 0.461999 0.884025 0.070 Uiso 1 1 calc R U . . .
C15 C 0.0703(15) 0.0741(9) 0.3927(7) 0.074(3) Uani 1 1 d . . . . .
H15A H 0.013375 -0.021532 0.384799 0.110 Uiso 1 1 calc R U . . .
H15B H 0.136398 0.088851 0.324290 0.110 Uiso 1 1 calc R U . . .
H15C H -0.048416 0.141280 0.411091 0.110 Uiso 1 1 calc R U . . .
C16 C 0.3625(13) 0.2772(9) 0.4911(7) 0.069(2) Uani 1 1 d . . . . .
H16A H 0.432323 0.318487 0.559672 0.104 Uiso 1 1 calc R U . . .
H16B H 0.236884 0.334414 0.477284 0.104 Uiso 1 1 calc R U . . .
H16C H 0.466318 0.274052 0.431598 0.104 Uiso 1 1 calc R U . . .
S21 S 0.7602(3) 0.5936(2) 0.48196(16) 0.0575(6) Uani 1 1 d . . . . .
O21 O 1.2533(10) 0.4325(6) 0.0799(4) 0.0708(16) Uani 1 1 d . . . . .
O22 O 1.1493(7) 0.7380(5) 0.3913(4) 0.0496(12) Uani 1 1 d . . . . .
O23 O 0.6543(10) 0.3577(7) 0.3060(5) 0.0851(19) Uani 1 1 d . . . . .
C22 C 1.4067(16) 0.5402(9) 0.0848(8) 0.084(3) Uani 1 1 d . . . . .
H22A H 1.388079 0.589418 0.021649 0.101 Uiso 1 1 calc R U . . .
H22B H 1.555400 0.500718 0.082985 0.101 Uiso 1 1 calc R U . . .
C23 C 1.3717(11) 0.6445(7) 0.1927(6) 0.0487(18) Uani 1 1 d . . . . .
H23A H 1.494294 0.637465 0.244625 0.058 Uiso 1 1 calc R U . . .
N24 N 1.1702(9) 0.5867(6) 0.2318(5) 0.0515(17) Uani 1 1 d . . . . .
C25 C 1.0795(10) 0.6302(7) 0.3329(5) 0.0397(16) Uani 1 1 d . . . . .
C26 C 0.9001(11) 0.5466(7) 0.3591(6) 0.0415(17) Uani 1 1 d . . . . .
C27 C 0.8174(12) 0.4251(8) 0.2897(6) 0.0542(19) Uani 1 1 d . . . . .
C28 C 0.9452(16) 0.3821(10) 0.1842(7) 0.081(3) Uani 1 1 d . . . . .
H28A H 0.966079 0.279183 0.173667 0.097 Uiso 1 1 calc R U . . .
H28B H 0.853460 0.402717 0.123193 0.097 Uiso 1 1 calc R U . . .
C28A C 1.141(2) 0.4413(11) 0.1758(10) 0.118(5) Uani 1 1 d . . . . .
H28C H 1.236701 0.387268 0.219450 0.142 Uiso 1 1 calc R U . . .
C29 C 1.3481(11) 0.7941(7) 0.1715(5) 0.0469(18) Uani 1 1 d . . . . .
C30 C 1.5290(13) 0.8839(9) 0.1934(7) 0.068(2) Uani 1 1 d . . . . .
H30A H 1.655978 0.854286 0.226951 0.081 Uiso 1 1 calc R U . . .
C31 C 1.517(2) 1.0185(13) 0.1642(11) 0.105(4) Uani 1 1 d . . . . .
H31A H 1.636754 1.080139 0.178141 0.126 Uiso 1 1 calc R U . . .
C32 C 1.333(3) 1.0616(12) 0.1160(10) 0.110(5) Uani 1 1 d . . . . .
H32A H 1.327379 1.151840 0.095361 0.132 Uiso 1 1 calc R U . . .
C33 C 1.158(2) 0.9740(13) 0.0977(7) 0.088(3) Uani 1 1 d . . . . .
H33A H 1.030648 1.004481 0.065147 0.106 Uiso 1 1 calc R U . . .
C34 C 1.1647(12) 0.8422(8) 0.1259(6) 0.056(2) Uani 1 1 d . . . . .
H34A H 1.040548 0.783577 0.113633 0.067 Uiso 1 1 calc R U . . .
C35 C 0.6701(13) 0.7725(8) 0.4871(7) 0.069(2) Uani 1 1 d . . . . .
H35A H 0.541035 0.774350 0.440926 0.103 Uiso 1 1 calc R U . . .
H35B H 0.785934 0.827500 0.461039 0.103 Uiso 1 1 calc R U . . .
H35C H 0.634331 0.812830 0.562178 0.103 Uiso 1 1 calc R U . . .
C36 C 0.9618(14) 0.6159(9) 0.5880(6) 0.070(2) Uani 1 1 d . . . . .
H36A H 1.027229 0.524892 0.593887 0.104 Uiso 1 1 calc R U . . .
H36B H 0.893677 0.654987 0.657141 0.104 Uiso 1 1 calc R U . . .
H36C H 1.074571 0.679977 0.570946 0.104 Uiso 1 1 calc R U . . .


_geom_special_details            ?

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
S1 C6 1.736(7) . ?
S1 C15 1.791(9) . ?
S1 C16 1.810(8) . ?
O1 C2 1.324(9) . ?
O1 C8AA 1.44(2) . ?
O1 C8AB 1.452(19) . ?
O2 C5 1.224(7) . ?
O3 C7 1.239(8) . ?
C2 C3 1.545(10) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 N4 1.454(8) . ?
C3 C9 1.505(9) . ?
C3 H3A 0.9900 . ?
N4 C5 1.374(8) . ?
N4 C8AA 1.444(17) . ?
N4 C8AB 1.571(17) . ?
C5 C6 1.436(9) . ?
C6 C7 1.425(10) . ?
C7 C8 1.522(10) . ?
C8 C8AB 1.37(2) . ?
C8 C8AA 1.41(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 H8D 0.9800 . ?
C8AA H8AA 0.9900 . ?
C8AB H8AB 0.9900 . ?
C9 C14 1.379(10) . ?
C9 C10 1.396(10) . ?
C10 C11 1.348(12) . ?
C10 H10A 0.9400 . ?
C11 C12 1.360(14) . ?
C11 H11A 0.9400 . ?
C12 C13 1.352(14) . ?
C12 H12A 0.9400 . ?
C13 C14 1.400(12) . ?
C13 H13A 0.9400 . ?
C14 H14A 0.9400 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
S21 C26 1.739(7) . ?
S21 C36 1.777(8) . ?
S21 C35 1.789(8) . ?
O21 C28A 1.362(10) . ?
O21 C22 1.388(9) . ?
O22 C25 1.234(8) . ?
O23 C27 1.223(8) . ?
C22 C23 1.546(10) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C23 N24 1.466(9) . ?
C23 C29 1.503(10) . ?
C23 H23A 0.9900 . ?
N24 C25 1.369(8) . ?
N24 C28A 1.461(10) . ?
C25 C26 1.427(9) . ?
C26 C27 1.419(10) . ?
C27 C28 1.520(10) . ?
C28 C28A 1.337(12) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28A H28C 0.9900 . ?
C29 C34 1.361(10) . ?
C29 C30 1.398(10) . ?
C30 C31 1.395(14) . ?
C30 H30A 0.9400 . ?
C31 C32 1.358(18) . ?
C31 H31A 0.9400 . ?
C32 C33 1.353(17) . ?
C32 H32A 0.9400 . ?
C33 C34 1.363(12) . ?
C33 H33A 0.9400 . ?
C34 H34A 0.9400 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 H35C 0.9700 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 H36C 0.9700 . ?

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
C6 S1 C15 107.6(4) . . ?
C6 S1 C16 107.2(4) . . ?
C15 S1 C16 100.4(4) . . ?
C2 O1 C8AA 109.6(9) . . ?
C2 O1 C8AB 107.9(8) . . ?
O1 C2 C3 110.9(6) . . ?
O1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
O1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.0 . . ?
N4 C3 C9 114.6(6) . . ?
N4 C3 C2 98.5(6) . . ?
C9 C3 C2 112.7(6) . . ?
N4 C3 H3A 110.1 . . ?
C9 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
C5 N4 C8AA 124.5(7) . . ?
C5 N4 C3 123.4(6) . . ?
C8AA N4 C3 112.1(7) . . ?
C5 N4 C8AB 115.3(8) . . ?
C3 N4 C8AB 105.6(7) . . ?
O2 C5 N4 120.6(6) . . ?
O2 C5 C6 124.5(6) . . ?
N4 C5 C6 114.9(6) . . ?
C7 C6 C5 124.1(6) . . ?
C7 C6 S1 115.2(5) . . ?
C5 C6 S1 120.7(5) . . ?
O3 C7 C6 125.2(7) . . ?
O3 C7 C8 120.2(7) . . ?
C6 C7 C8 114.6(6) . . ?
C8AB C8 C7 116.6(9) . . ?
C8AA C8 C7 116.5(9) . . ?
C8AA C8 H8A 108.2 . . ?
C7 C8 H8A 108.2 . . ?
C8AA C8 H8B 108.2 . . ?
C7 C8 H8B 108.2 . . ?
H8A C8 H8B 107.3 . . ?
C8AB C8 H8C 108.1 . . ?
C7 C8 H8C 108.1 . . ?
C8AB C8 H8D 108.1 . . ?
C7 C8 H8D 108.1 . . ?
H8C C8 H8D 107.3 . . ?
C8 C8AA O1 111(2) . . ?
C8 C8AA N4 113.1(17) . . ?
O1 C8AA N4 102.1(14) . . ?
C8 C8AA H8AA 110.0 . . ?
O1 C8AA H8AA 110.0 . . ?
N4 C8AA H8AA 110.0 . . ?
C8 C8AB O1 112.7(17) . . ?
C8 C8AB N4 107.7(15) . . ?
O1 C8AB N4 95.7(12) . . ?
C8 C8AB H8AB 113.1 . . ?
O1 C8AB H8AB 113.1 . . ?
N4 C8AB H8AB 113.1 . . ?
C14 C9 C10 117.9(7) . . ?
C14 C9 C3 123.1(7) . . ?
C10 C9 C3 118.9(6) . . ?
C11 C10 C9 122.1(8) . . ?
C11 C10 H10A 119.0 . . ?
C9 C10 H10A 119.0 . . ?
C10 C11 C12 119.5(9) . . ?
C10 C11 H11A 120.3 . . ?
C12 C11 H11A 120.3 . . ?
C13 C12 C11 120.8(10) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C12 C13 C14 120.5(9) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C9 C14 C13 119.2(8) . . ?
C9 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C26 S21 C36 106.6(4) . . ?
C26 S21 C35 107.0(4) . . ?
C36 S21 C35 100.6(4) . . ?
C28A O21 C22 111.5(6) . . ?
O21 C22 C23 108.2(6) . . ?
O21 C22 H22A 110.1 . . ?
C23 C22 H22A 110.1 . . ?
O21 C22 H22B 110.1 . . ?
C23 C22 H22B 110.1 . . ?
H22A C22 H22B 108.4 . . ?
N24 C23 C29 113.7(5) . . ?
N24 C23 C22 100.2(6) . . ?
C29 C23 C22 111.3(6) . . ?
N24 C23 H23A 110.4 . . ?
C29 C23 H23A 110.4 . . ?
C22 C23 H23A 110.4 . . ?
C25 N24 C28A 120.4(6) . . ?
C25 N24 C23 124.7(6) . . ?
C28A N24 C23 109.1(6) . . ?
O22 C25 N24 119.5(6) . . ?
O22 C25 C26 125.3(6) . . ?
N24 C25 C26 115.1(6) . . ?
C27 C26 C25 124.7(6) . . ?
C27 C26 S21 114.9(5) . . ?
C25 C26 S21 120.3(5) . . ?
O23 C27 C26 126.3(7) . . ?
O23 C27 C28 119.2(7) . . ?
C26 C27 C28 114.5(6) . . ?
C28A C28 C27 118.1(7) . . ?
C28A C28 H28A 107.8 . . ?
C27 C28 H28A 107.8 . . ?
C28A C28 H28B 107.8 . . ?
C27 C28 H28B 107.8 . . ?
H28A C28 H28B 107.1 . . ?
C28 C28A O21 123.8(10) . . ?
C28 C28A N24 117.1(8) . . ?
O21 C28A N24 105.6(7) . . ?
C28 C28A H28C 102.3 . . ?
O21 C28A H28C 102.3 . . ?
N24 C28A H28C 102.3 . . ?
C34 C29 C30 119.1(7) . . ?
C34 C29 C23 122.8(7) . . ?
C30 C29 C23 117.9(7) . . ?
C31 C30 C29 118.4(10) . . ?
C31 C30 H30A 120.8 . . ?
C29 C30 H30A 120.8 . . ?
C32 C31 C30 120.9(11) . . ?
C32 C31 H31A 119.6 . . ?
C30 C31 H31A 119.6 . . ?
C33 C32 C31 119.7(10) . . ?
C33 C32 H32A 120.2 . . ?
C31 C32 H32A 120.2 . . ?
C32 C33 C34 120.9(10) . . ?
C32 C33 H33A 119.6 . . ?
C34 C33 H33A 119.6 . . ?
C29 C34 C33 121.0(9) . . ?
C29 C34 H34A 119.5 . . ?
C33 C34 H34A 119.5 . . ?
S21 C35 H35A 109.5 . . ?
S21 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
S21 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
S21 C36 H36A 109.5 . . ?
S21 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
S21 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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
C8AA O1 C2 C3 19.1(18) . . . . ?
C8AB O1 C2 C3 -26.6(15) . . . . ?
O1 C2 C3 N4 -3.6(10) . . . . ?
O1 C2 C3 C9 -125.0(8) . . . . ?
C9 C3 N4 C5 -74.7(9) . . . . ?
C2 C3 N4 C5 165.4(7) . . . . ?
C9 C3 N4 C8AA 106.6(18) . . . . ?
C2 C3 N4 C8AA -13.3(18) . . . . ?
C9 C3 N4 C8AB 149.6(11) . . . . ?
C2 C3 N4 C8AB 29.7(12) . . . . ?
C8AA N4 C5 O2 -167.1(19) . . . . ?
C3 N4 C5 O2 14.4(11) . . . . ?
C8AB N4 C5 O2 146.3(12) . . . . ?
C8AA N4 C5 C6 12(2) . . . . ?
C3 N4 C5 C6 -166.9(7) . . . . ?
C8AB N4 C5 C6 -35.0(13) . . . . ?
O2 C5 C6 C7 -177.6(7) . . . . ?
N4 C5 C6 C7 3.7(11) . . . . ?
O2 C5 C6 S1 3.1(10) . . . . ?
N4 C5 C6 S1 -175.5(6) . . . . ?
C15 S1 C6 C7 128.8(6) . . . . ?
C16 S1 C6 C7 -124.0(6) . . . . ?
C15 S1 C6 C5 -51.9(7) . . . . ?
C16 S1 C6 C5 55.3(7) . . . . ?
C5 C6 C7 O3 -175.4(8) . . . . ?
S1 C6 C7 O3 3.9(11) . . . . ?
C5 C6 C7 C8 4.3(12) . . . . ?
S1 C6 C7 C8 -176.4(7) . . . . ?
O3 C7 C8 C8AB -157.3(15) . . . . ?
C6 C7 C8 C8AB 23.0(18) . . . . ?
O3 C7 C8 C8AA 152.0(18) . . . . ?
C6 C7 C8 C8AA -28(2) . . . . ?
C7 C8 C8AA O1 155.3(12) . . . . ?
C7 C8 C8AA N4 41(3) . . . . ?
C2 O1 C8AA C8 -147.1(15) . . . . ?
C2 O1 C8AA N4 -26(2) . . . . ?
C5 N4 C8AA C8 -35(3) . . . . ?
C3 N4 C8AA C8 144.1(16) . . . . ?
C5 N4 C8AA O1 -154.4(10) . . . . ?
C3 N4 C8AA O1 24(2) . . . . ?
C7 C8 C8AB O1 -155.2(10) . . . . ?
C7 C8 C8AB N4 -51(2) . . . . ?
C2 O1 C8AB C8 153.9(13) . . . . ?
C2 O1 C8AB N4 42.0(15) . . . . ?
C5 N4 C8AB C8 59.7(19) . . . . ?
C3 N4 C8AB C8 -160.5(12) . . . . ?
C5 N4 C8AB O1 175.8(9) . . . . ?
C3 N4 C8AB O1 -44.4(15) . . . . ?
N4 C3 C9 C14 -40.7(9) . . . . ?
C2 C3 C9 C14 71.0(8) . . . . ?
N4 C3 C9 C10 143.0(6) . . . . ?
C2 C3 C9 C10 -105.4(7) . . . . ?
C14 C9 C10 C11 0.2(11) . . . . ?
C3 C9 C10 C11 176.8(7) . . . . ?
C9 C10 C11 C12 -0.5(13) . . . . ?
C10 C11 C12 C13 0.6(14) . . . . ?
C11 C12 C13 C14 -0.5(14) . . . . ?
C10 C9 C14 C13 -0.1(10) . . . . ?
C3 C9 C14 C13 -176.5(6) . . . . ?
C12 C13 C14 C9 0.2(12) . . . . ?
C28A O21 C22 C23 -8.0(12) . . . . ?
O21 C22 C23 N24 -6.9(9) . . . . ?
O21 C22 C23 C29 -127.6(8) . . . . ?
C29 C23 N24 C25 -69.4(9) . . . . ?
C22 C23 N24 C25 171.8(7) . . . . ?
C29 C23 N24 C28A 137.3(9) . . . . ?
C22 C23 N24 C28A 18.5(10) . . . . ?
C28A N24 C25 O22 161.3(9) . . . . ?
C23 N24 C25 O22 10.8(10) . . . . ?
C28A N24 C25 C26 -21.5(11) . . . . ?
C23 N24 C25 C26 -172.0(6) . . . . ?
O22 C25 C26 C27 178.1(7) . . . . ?
N24 C25 C26 C27 1.1(10) . . . . ?
O22 C25 C26 S21 -0.1(10) . . . . ?
N24 C25 C26 S21 -177.1(5) . . . . ?
C36 S21 C26 C27 129.7(6) . . . . ?
C35 S21 C26 C27 -123.4(6) . . . . ?
C36 S21 C26 C25 -51.9(7) . . . . ?
C35 S21 C26 C25 55.0(7) . . . . ?
C25 C26 C27 O23 -174.1(8) . . . . ?
S21 C26 C27 O23 4.1(11) . . . . ?
C25 C26 C27 C28 3.7(11) . . . . ?
S21 C26 C27 C28 -178.1(6) . . . . ?
O23 C27 C28 C28A -169.1(11) . . . . ?
C26 C27 C28 C28A 12.9(14) . . . . ?
C27 C28 C28A O21 -167.4(9) . . . . ?
C27 C28 C28A N24 -32.6(17) . . . . ?
C22 O21 C28A C28 158.7(12) . . . . ?
C22 O21 C28A N24 19.6(13) . . . . ?
C25 N24 C28A C28 38.8(16) . . . . ?
C23 N24 C28A C28 -166.6(11) . . . . ?
C25 N24 C28A O21 -179.0(8) . . . . ?
C23 N24 C28A O21 -24.4(12) . . . . ?
N24 C23 C29 C34 -38.8(9) . . . . ?
C22 C23 C29 C34 73.5(8) . . . . ?
N24 C23 C29 C30 145.4(7) . . . . ?
C22 C23 C29 C30 -102.3(8) . . . . ?
C34 C29 C30 C31 -2.0(11) . . . . ?
C23 C29 C30 C31 173.9(7) . . . . ?
C29 C30 C31 C32 0.2(15) . . . . ?
C30 C31 C32 C33 1.2(17) . . . . ?
C31 C32 C33 C34 -0.8(16) . . . . ?
C30 C29 C34 C33 2.5(11) . . . . ?
C23 C29 C34 C33 -173.2(7) . . . . ?
C32 C33 C34 C29 -1.1(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8AB^b H8AB^b O3 0.99 2.61 3.47(3) 145.0 1_455 yes
C15 H15A O22 0.97 2.46 3.248(10) 138.6 1_445 yes
C15 H15C O2 0.97 2.42 3.094(9) 126.5 . yes
C16 H16C O23 0.97 2.19 3.103(9) 156.2 . yes
C35 H35A O22 0.97 2.47 3.378(10) 155.3 1_455 yes
C35 H35B O22 0.97 2.48 3.157(9) 126.5 . yes
C35 H35C O3 0.97 2.28 3.131(9) 146.1 1_565 yes
C36 H36A O2 0.97 2.53 3.278(10) 134.3 1_655 yes
C36 H36C O22 0.97 2.42 3.091(9) 125.9 . yes

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_23a
_database_code_depnum_ccdc_archive 'CCDC 2125366'
loop_
_audit_author_name
_audit_author_address
'Sylvain Bernes'
;Instituto de Fisica, BUAP, Puebla
Mexico
;
_audit_update_record             
;
2021-11-30 deposited with the CCDC.	2022-01-21 downloaded from the CCDC.
;

# Clave Lab.  :  ENR33_1
# Clave IF-UAP:  ENR33_1
# Clave datos : ... \BUAP\Sylvain\ENR33_1\50mm_1\

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_audit_creation_date             2018-02-13

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 N O3 S'
_chemical_formula_sum            'C16 H19 N O3 S'
_chemical_formula_weight         305.38
_chemical_absolute_configuration ad
_chemical_optical_rotation       ?

_chemical_properties_physical    ?
_chemical_properties_biological  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.0826 0.0763 '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       ?

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                   5.46490(10)
_cell_length_b                   10.7205(4)
_cell_length_c                   26.0834(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1528.13(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    27016
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      29.15

_exptl_crystal_recrystallization_method 
;
Re-crystallisation from solvent: CH2Cl2/benzine
;

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5466
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_diffrn_ambient_temperature      295(1)
_diffrn_ambient_environment      air
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_diffrn_source_current           0.600
_diffrn_source_power             0.039
_diffrn_radiation_collimation    '0.3 mm diameter'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
1619 frames, 35-45 s/frame, 1 deg./frame, detector distance = 50 mm
;
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            34956
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.885
_diffrn_reflns_theta_max         20.998
_diffrn_reflns_theta_full        19.664
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3324
_reflns_number_gt                3073
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          ?

_computing_data_collection       'X-AREA (Stoe & Cie, 2015)'
_computing_cell_refinement       X-AREA
_computing_data_reduction        X-AREA
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'

_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)+(0.0598P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.039(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1208 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_number_reflns         3324
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.37953(10) 0.36461(5) 0.27142(2) 0.04486(16) Uani 1 1 d . . . . .
O1 O 0.5974(3) 0.54107(16) 0.47647(6) 0.0507(4) Uani 1 1 d . . . . .
O2 O 0.2044(3) 0.58577(15) 0.32652(6) 0.0462(4) Uani 1 1 d . . . . .
O3 O 0.7885(3) 0.26374(17) 0.33920(7) 0.0585(4) Uani 1 1 d . . . . .
C2 C 0.4079(4) 0.6324(2) 0.48173(8) 0.0494(5) Uani 1 1 d . . . . .
H2A H 0.468312 0.706395 0.498983 0.059 Uiso 1 1 calc R U . . .
H2B H 0.270629 0.599097 0.500945 0.059 Uiso 1 1 calc R U . . .
C3 C 0.3334(4) 0.6621(2) 0.42647(7) 0.0392(4) Uani 1 1 d . . . . .
H3A H 0.158693 0.682430 0.424905 0.047 Uiso 1 1 calc R U . . .
N4 N 0.3782(3) 0.54116(15) 0.40287(6) 0.0370(4) Uani 1 1 d . . . . .
C5 C 0.3380(3) 0.51678(19) 0.35212(7) 0.0356(4) Uani 1 1 d . . . . .
C6 C 0.4663(4) 0.4084(2) 0.33239(8) 0.0407(4) Uani 1 1 d . . . . .
C7 C 0.6653(4) 0.3501(2) 0.35736(8) 0.0425(5) Uani 1 1 d . . . . .
C8 C 0.7334(4) 0.4030(2) 0.40951(9) 0.0465(5) Uani 1 1 d . . . . .
H8A H 0.803469 0.337125 0.430368 0.056 Uiso 1 1 calc R U . . .
H8B H 0.856998 0.466974 0.405075 0.056 Uiso 1 1 calc R U . . .
C8A C 0.5160(4) 0.4582(2) 0.43722(8) 0.0414(5) Uani 1 1 d . . . . .
C9 C 0.4833(4) 0.7678(2) 0.40424(7) 0.0381(4) Uani 1 1 d . . . . .
C10 C 0.4127(4) 0.8904(2) 0.41367(9) 0.0477(5) Uani 1 1 d . . . . .
H10A H 0.270025 0.906306 0.431980 0.057 Uiso 1 1 calc R U . . .
C11 C 0.5538(5) 0.9893(2) 0.39594(10) 0.0584(6) Uani 1 1 d . . . . .
H11A H 0.504617 1.070883 0.402347 0.070 Uiso 1 1 calc R U . . .
C12 C 0.7664(5) 0.9672(3) 0.36889(11) 0.0604(6) Uani 1 1 d . . . . .
H12A H 0.860724 1.033324 0.356993 0.072 Uiso 1 1 calc R U . . .
C13 C 0.8369(4) 0.8461(3) 0.35975(9) 0.0546(6) Uani 1 1 d . . . . .
H13A H 0.981052 0.830605 0.341899 0.066 Uiso 1 1 calc R U . . .
C14 C 0.6975(4) 0.7478(2) 0.37662(8) 0.0439(5) Uani 1 1 d . . . . .
H14A H 0.746932 0.666609 0.369478 0.053 Uiso 1 1 calc R U . . .
C15 C 0.3531(4) 0.3569(3) 0.45961(10) 0.0548(6) Uani 1 1 d . . . . .
H15A H 0.294739 0.304073 0.432526 0.082 Uiso 1 1 calc R U . . .
H15B H 0.216403 0.394692 0.476750 0.082 Uiso 1 1 calc R U . . .
H15C H 0.445186 0.308097 0.483673 0.082 Uiso 1 1 calc R U . . .
C16 C 0.6551(5) 0.3602(3) 0.23363(9) 0.0553(6) Uani 1 1 d . . . . .
H16A H 0.613332 0.358572 0.197891 0.083 Uiso 1 1 calc R U . . .
H16B H 0.747131 0.286824 0.242127 0.083 Uiso 1 1 calc R U . . .
H16C H 0.751711 0.432998 0.240739 0.083 Uiso 1 1 calc R U . . .
C17 C 0.3104(6) 0.2013(2) 0.27522(12) 0.0631(7) Uani 1 1 d . . . . .
H17A H 0.276957 0.169736 0.241497 0.095 Uiso 1 1 calc R U . . .
H17B H 0.169544 0.189165 0.296652 0.095 Uiso 1 1 calc R U . . .
H17C H 0.447581 0.157587 0.289553 0.095 Uiso 1 1 calc R U . . .


_geom_special_details            ?

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
S1 C6 1.725(2) . ?
S1 C17 1.794(3) . ?
S1 C16 1.800(2) . ?
O1 C8A 1.427(3) . ?
O1 C2 1.432(3) . ?
O2 C5 1.235(2) . ?
O3 C7 1.239(3) . ?
C2 C3 1.531(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N4 1.456(3) . ?
C3 C9 1.514(3) . ?
C3 H3A 0.9800 . ?
N4 C5 1.367(2) . ?
N4 C8A 1.470(3) . ?
C5 C6 1.451(3) . ?
C6 C7 1.413(3) . ?
C7 C8 1.520(3) . ?
C8 C8A 1.511(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8A C15 1.521(3) . ?
C9 C14 1.391(3) . ?
C9 C10 1.392(3) . ?
C10 C11 1.390(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.380(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.375(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.373(3) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C6 S1 C17 105.82(13) . . ?
C6 S1 C16 106.38(11) . . ?
C17 S1 C16 100.44(13) . . ?
C8A O1 C2 105.59(16) . . ?
O1 C2 C3 104.13(16) . . ?
O1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
O1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
N4 C3 C9 114.44(16) . . ?
N4 C3 C2 99.69(17) . . ?
C9 C3 C2 111.85(17) . . ?
N4 C3 H3A 110.1 . . ?
C9 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
C5 N4 C3 123.56(17) . . ?
C5 N4 C8A 123.83(17) . . ?
C3 N4 C8A 111.54(16) . . ?
O2 C5 N4 120.25(18) . . ?
O2 C5 C6 124.97(18) . . ?
N4 C5 C6 114.78(18) . . ?
C7 C6 C5 124.21(19) . . ?
C7 C6 S1 121.06(16) . . ?
C5 C6 S1 114.35(15) . . ?
O3 C7 C6 124.9(2) . . ?
O3 C7 C8 119.19(19) . . ?
C6 C7 C8 115.84(19) . . ?
C8A C8 C7 112.44(17) . . ?
C8A C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C8A C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
O1 C8A N4 102.74(16) . . ?
O1 C8A C8 110.00(17) . . ?
N4 C8A C8 110.38(16) . . ?
O1 C8A C15 110.59(19) . . ?
N4 C8A C15 111.47(16) . . ?
C8 C8A C15 111.4(2) . . ?
C14 C9 C10 118.1(2) . . ?
C14 C9 C3 122.54(19) . . ?
C10 C9 C3 119.30(18) . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
C13 C12 C11 119.2(2) . . ?
C13 C12 H12A 120.4 . . ?
C11 C12 H12A 120.4 . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C13 C14 C9 120.9(2) . . ?
C13 C14 H14A 119.5 . . ?
C9 C14 H14A 119.5 . . ?
C8A C15 H15A 109.5 . . ?
C8A C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8A C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C8A O1 C2 C3 -41.9(2) . . . . ?
O1 C2 C3 N4 31.8(2) . . . . ?
O1 C2 C3 C9 -89.5(2) . . . . ?
C9 C3 N4 C5 -60.9(2) . . . . ?
C2 C3 N4 C5 179.65(18) . . . . ?
C9 C3 N4 C8A 107.68(18) . . . . ?
C2 C3 N4 C8A -11.8(2) . . . . ?
C3 N4 C5 O2 -18.6(3) . . . . ?
C8A N4 C5 O2 174.29(19) . . . . ?
C3 N4 C5 C6 160.33(18) . . . . ?
C8A N4 C5 C6 -6.8(3) . . . . ?
O2 C5 C6 C7 162.5(2) . . . . ?
N4 C5 C6 C7 -16.3(3) . . . . ?
O2 C5 C6 S1 -10.5(3) . . . . ?
N4 C5 C6 S1 170.70(14) . . . . ?
C17 S1 C6 C7 58.1(2) . . . . ?
C16 S1 C6 C7 -48.1(2) . . . . ?
C17 S1 C6 C5 -128.66(17) . . . . ?
C16 S1 C6 C5 125.11(17) . . . . ?
C5 C6 C7 O3 -174.1(2) . . . . ?
S1 C6 C7 O3 -1.6(3) . . . . ?
C5 C6 C7 C8 3.6(3) . . . . ?
S1 C6 C7 C8 176.17(15) . . . . ?
O3 C7 C8 C8A -152.6(2) . . . . ?
C6 C7 C8 C8A 29.5(3) . . . . ?
C2 O1 C8A N4 33.3(2) . . . . ?
C2 O1 C8A C8 150.84(18) . . . . ?
C2 O1 C8A C15 -85.7(2) . . . . ?
C5 N4 C8A O1 156.18(17) . . . . ?
C3 N4 C8A O1 -12.3(2) . . . . ?
C5 N4 C8A C8 38.9(3) . . . . ?
C3 N4 C8A C8 -129.58(18) . . . . ?
C5 N4 C8A C15 -85.4(2) . . . . ?
C3 N4 C8A C15 106.1(2) . . . . ?
C7 C8 C8A O1 -160.80(18) . . . . ?
C7 C8 C8A N4 -48.1(2) . . . . ?
C7 C8 C8A C15 76.2(2) . . . . ?
N4 C3 C9 C14 -20.1(3) . . . . ?
C2 C3 C9 C14 92.3(2) . . . . ?
N4 C3 C9 C10 163.15(19) . . . . ?
C2 C3 C9 C10 -84.4(2) . . . . ?
C14 C9 C10 C11 -0.2(3) . . . . ?
C3 C9 C10 C11 176.7(2) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C9 -1.2(4) . . . . ?
C10 C9 C14 C13 0.9(3) . . . . ?
C3 C9 C14 C13 -175.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C16 H16B O3 0.96 2.55 3.030(3) 110.8 . yes
C17 H17B O3 0.96 2.49 3.371(4) 152.4 1_455 yes
C17 H17C O3 0.96 2.54 3.172(4) 123.6 . yes

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_32a
_database_code_depnum_ccdc_archive 'CCDC 2125369'
loop_
_audit_author_name
_audit_author_address
'Sylvain Bernes'
;Instituto de Fisica, BUAP, Puebla
Mexico
;
_audit_update_record             
;
2021-11-30 deposited with the CCDC.	2022-01-21 downloaded from the CCDC.
;

# Clave Lab.  :  ENR-194-2
# Clave IF-UAP:  ENR194_2
# Solicitud: 160
# Firma en la Solicitud: Dr. Joel Teran (ICUAP)
# Clave datos : ... \BUAP\Sylvain\ENR194_2\40mm_2\

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_audit_creation_date             2018-09-10

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N O3'
_chemical_formula_sum            'C14 H17 N O3'
_chemical_formula_weight         247.28
_chemical_absolute_configuration syn
_chemical_optical_rotation       ?

_chemical_properties_physical    ?
_chemical_properties_biological  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       ?

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

_cell_length_a                   11.5839(15)
_cell_length_b                   6.9820(5)
_cell_length_c                   16.333(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.429(10)
_cell_angle_gamma                90
_cell_volume                     1290.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    7259
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      25.51

_exptl_crystal_recrystallization_method 
;
Re-crystallisation from solvent: CH2Cl2/Petroleum benzine
;

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.056
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3987
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'X-AREA 1.82 (Stoe & Cie, 2018)'

_diffrn_ambient_temperature      295(1)
_diffrn_ambient_environment      air
_diffrn_measurement_specimen_support Mitegen
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_diffrn_source_current           0.600
_diffrn_source_power             0.039
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
1148 frames, 70 s/frame, 1 deg./frame, detector distance = 40 mm
;
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            29502
_diffrn_reflns_av_unetI/netI     0.2294
_diffrn_reflns_av_R_equivalents  0.1823
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.513
_diffrn_reflns_theta_max         20.988
_diffrn_reflns_theta_full        19.664
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             5371
_reflns_number_gt                1684
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_max     0.905
_reflns_Friedel_fraction_full    0.901

_reflns_special_details          ?

_computing_data_collection       'X-AREA 1.82 (Stoe & Cie, 2018)'
_computing_cell_refinement       'X-AREA 1.82'
_computing_data_reduction        'X-AREA 1.82'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'

_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)+(0.0405P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ? # -0.3(10)
_refine_ls_number_reflns         5371
_refine_ls_number_parameters     329
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1941
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   0.713
_refine_ls_restrained_S_all      0.713
_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 0.5626(4) 0.0545(6) 0.7943(3) 0.0675(14) Uani 1 1 d . . . . .
C2 C 0.4553(7) 0.0007(8) 0.8152(4) 0.074(2) Uani 1 1 d . . . . .
H2A H 0.465038 -0.013181 0.875397 0.089 Uiso 1 1 calc R U . . .
H2B H 0.426610 -0.119344 0.788472 0.089 Uiso 1 1 calc R U . . .
C3 C 0.3687(6) 0.1676(8) 0.7817(4) 0.0538(18) Uani 1 1 d . . . . .
H3A H 0.289243 0.116655 0.759749 0.065 Uiso 1 1 calc R U . . .
N4 N 0.4206(4) 0.2304(7) 0.7131(3) 0.0443(13) Uani 1 1 d . . . . .
C5 C 0.3748(6) 0.3675(9) 0.6588(4) 0.0518(17) Uani 1 1 d . . . . .
O5 O 0.2787(4) 0.4408(6) 0.6598(2) 0.0703(13) Uani 1 1 d . . . . .
C6 C 0.4478(6) 0.4198(10) 0.5958(4) 0.0628(18) Uani 1 1 d . . . . .
H6A H 0.426361 0.548544 0.575905 0.075 Uiso 1 1 calc R U . . .
H6B H 0.426260 0.334258 0.548193 0.075 Uiso 1 1 calc R U . . .
C7 C 0.5817(6) 0.4121(11) 0.6269(4) 0.071(2) Uani 1 1 d . . . . .
H7A H 0.609340 0.541503 0.644329 0.085 Uiso 1 1 calc R U . . .
O7 O 0.6297(4) 0.3602(10) 0.5573(3) 0.0915(16) Uani 1 1 d . . . . .
H7 H 0.701735 0.350955 0.572138 0.137 Uiso 1 1 calc R U . . .
C8 C 0.6219(6) 0.2789(10) 0.7007(4) 0.070(2) Uani 1 1 d . . . . .
H8A H 0.641981 0.355411 0.751329 0.084 Uiso 1 1 calc R U . . .
H8B H 0.693311 0.214325 0.693797 0.084 Uiso 1 1 calc R U . . .
C8A C 0.5325(6) 0.1287(8) 0.7126(4) 0.0557(18) Uani 1 1 d . . . . .
C9 C 0.3645(6) 0.3146(8) 0.8472(4) 0.0467(16) Uani 1 1 d . . . . .
C10 C 0.4542(6) 0.4486(9) 0.8731(4) 0.0532(16) Uani 1 1 d . . . . .
H10A H 0.517155 0.453973 0.846238 0.064 Uiso 1 1 calc R U . . .
C11 C 0.4508(7) 0.5733(9) 0.9382(4) 0.064(2) Uani 1 1 d . . . . .
H11A H 0.511219 0.661643 0.955337 0.077 Uiso 1 1 calc R U . . .
C12 C 0.3561(8) 0.5651(11) 0.9776(4) 0.073(2) Uani 1 1 d . . . . .
H12A H 0.353534 0.648462 1.021543 0.088 Uiso 1 1 calc R U . . .
C13 C 0.2687(7) 0.4392(13) 0.9532(5) 0.077(2) Uani 1 1 d . . . . .
H13A H 0.205065 0.436490 0.979603 0.092 Uiso 1 1 calc R U . . .
C14 C 0.2730(6) 0.3137(9) 0.8891(4) 0.0588(19) Uani 1 1 d . . . . .
H14A H 0.212198 0.225228 0.873464 0.071 Uiso 1 1 calc R U . . .
C15 C 0.5161(7) -0.0297(10) 0.6470(4) 0.091(2) Uani 1 1 d . . . . .
H15A H 0.461612 -0.123241 0.659435 0.136 Uiso 1 1 calc R U . . .
H15B H 0.590883 -0.089738 0.647689 0.136 Uiso 1 1 calc R U . . .
H15C H 0.485549 0.024023 0.592559 0.136 Uiso 1 1 calc R U . . .
O21 O 1.0900(4) 0.9386(5) 0.7543(3) 0.0599(12) Uani 1 1 d . . . . .
C22 C 1.1324(6) 0.7604(9) 0.7916(4) 0.068(2) Uani 1 1 d . . . . .
H22A H 1.138867 0.764236 0.851736 0.081 Uiso 1 1 calc R U . . .
H22B H 1.209441 0.730858 0.780470 0.081 Uiso 1 1 calc R U . . .
C23 C 1.0405(5) 0.6104(8) 0.7508(4) 0.0503(17) Uani 1 1 d . . . . .
H23A H 1.080003 0.492317 0.739341 0.060 Uiso 1 1 calc R U . . .
N24 N 0.9884(4) 0.7078(6) 0.6725(3) 0.0466(14) Uani 1 1 d . . . . .
C25 C 0.8942(6) 0.6402(9) 0.6188(4) 0.0514(17) Uani 1 1 d . . . . .
O25 O 0.8562(4) 0.4771(5) 0.6253(3) 0.0637(13) Uani 1 1 d . . . . .
C26 C 0.8296(7) 0.7742(8) 0.5536(4) 0.084(3) Uani 1 1 d . . . . .
H26A H 0.835336 0.723127 0.499347 0.100 Uiso 1 1 calc R U . . .
H26B H 0.746727 0.769815 0.556130 0.100 Uiso 1 1 calc R U . . .
C27 C 0.8645(7) 0.9777(10) 0.5553(4) 0.069(2) Uani 1 1 d . . . . .
H27A H 0.793292 1.057635 0.545910 0.083 Uiso 1 1 calc R U . . .
O27 O 0.9186(7) 0.9952(12) 0.4856(4) 0.161(3) Uani 1 1 d . . . . .
H27 H 0.880137 0.935075 0.445783 0.242 Uiso 1 1 calc R U . . .
C28 C 0.9472(6) 1.0420(8) 0.6330(4) 0.064(2) Uani 1 1 d . . . . .
H28A H 0.902353 1.069653 0.675303 0.077 Uiso 1 1 calc R U . . .
H28B H 0.984742 1.160113 0.621210 0.077 Uiso 1 1 calc R U . . .
C28A C 1.0423(6) 0.8970(8) 0.6679(4) 0.0478(16) Uani 1 1 d . . . . .
C29 C 0.9506(6) 0.5675(10) 0.8038(4) 0.0590(19) Uani 1 1 d . . . . .
C30 C 0.8719(8) 0.7039(11) 0.8173(5) 0.082(2) Uani 1 1 d . . . . .
H30A H 0.869760 0.821275 0.790015 0.098 Uiso 1 1 calc R U . . .
C31 C 0.7937(8) 0.6711(15) 0.8715(6) 0.103(3) Uani 1 1 d . . . . .
H31A H 0.740181 0.765189 0.879249 0.123 Uiso 1 1 calc R U . . .
C32 C 0.7976(10) 0.5014(18) 0.9119(6) 0.113(4) Uani 1 1 d . . . . .
H32A H 0.748007 0.479557 0.948743 0.135 Uiso 1 1 calc R U . . .
C33 C 0.8758(8) 0.3596(16) 0.8985(6) 0.105(3) Uani 1 1 d . . . . .
H33A H 0.878164 0.242626 0.926019 0.126 Uiso 1 1 calc R U . . .
C34 C 0.9510(6) 0.3936(11) 0.8431(5) 0.082(2) Uani 1 1 d . . . . .
H34A H 1.001587 0.297298 0.832965 0.099 Uiso 1 1 calc R U . . .
C35 C 1.1420(5) 0.8884(8) 0.6200(4) 0.0594(18) Uani 1 1 d . . . . .
H35A H 1.195496 0.786799 0.642194 0.089 Uiso 1 1 calc R U . . .
H35B H 1.183894 1.008032 0.626139 0.089 Uiso 1 1 calc R U . . .
H35C H 1.109332 0.865092 0.561731 0.089 Uiso 1 1 calc R U . . .


_geom_special_details            ?

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 C8A 1.403(7) . ?
O1 C2 1.409(8) . ?
C2 C3 1.558(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N4 1.449(7) . ?
C3 C9 1.490(8) . ?
C3 H3A 0.9800 . ?
N4 C5 1.335(7) . ?
N4 C8A 1.480(7) . ?
C5 O5 1.229(7) . ?
C5 C6 1.509(8) . ?
C6 C7 1.526(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O7 1.416(7) . ?
C7 C8 1.514(8) . ?
C7 H7A 0.9800 . ?
O7 H7 0.8200 . ?
C8 C8A 1.515(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8A C15 1.523(8) . ?
C9 C14 1.380(8) . ?
C9 C10 1.394(7) . ?
C10 C11 1.381(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.387(9) . ?
C11 H11A 0.9300 . ?
C12 C13 1.336(10) . ?
C12 H12A 0.9300 . ?
C13 C14 1.375(9) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O21 C22 1.425(6) . ?
O21 C28A 1.432(6) . ?
C22 C23 1.539(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 N24 1.459(7) . ?
C23 C29 1.521(8) . ?
C23 H23A 0.9800 . ?
N24 C25 1.331(7) . ?
N24 C28A 1.470(7) . ?
C25 O25 1.234(7) . ?
C25 C26 1.492(8) . ?
C26 C27 1.476(8) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 O27 1.419(8) . ?
C27 C28 1.486(8) . ?
C27 H27A 0.9800 . ?
O27 H27 0.8200 . ?
C28 C28A 1.514(7) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28A C35 1.528(8) . ?
C29 C30 1.369(9) . ?
C29 C34 1.373(9) . ?
C30 C31 1.416(9) . ?
C30 H30A 0.9300 . ?
C31 C32 1.352(11) . ?
C31 H31A 0.9300 . ?
C32 C33 1.391(11) . ?
C32 H32A 0.9300 . ?
C33 C34 1.404(10) . ?
C33 H33A 0.9300 . ?
C34 H34A 0.9300 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?

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
C8A O1 C2 106.1(5) . . ?
O1 C2 C3 104.5(5) . . ?
O1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
O1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
N4 C3 C9 115.5(5) . . ?
N4 C3 C2 98.9(5) . . ?
C9 C3 C2 112.4(5) . . ?
N4 C3 H3A 109.9 . . ?
C9 C3 H3A 109.9 . . ?
C2 C3 H3A 109.9 . . ?
C5 N4 C3 124.1(6) . . ?
C5 N4 C8A 124.3(6) . . ?
C3 N4 C8A 111.7(5) . . ?
O5 C5 N4 121.4(7) . . ?
O5 C5 C6 123.4(6) . . ?
N4 C5 C6 115.2(6) . . ?
C5 C6 C7 116.3(5) . . ?
C5 C6 H6A 108.2 . . ?
C7 C6 H6A 108.2 . . ?
C5 C6 H6B 108.2 . . ?
C7 C6 H6B 108.2 . . ?
H6A C6 H6B 107.4 . . ?
O7 C7 C8 112.0(6) . . ?
O7 C7 C6 106.8(5) . . ?
C8 C7 C6 113.7(6) . . ?
O7 C7 H7A 108.0 . . ?
C8 C7 H7A 108.0 . . ?
C6 C7 H7A 108.0 . . ?
C7 O7 H7 109.5 . . ?
C7 C8 C8A 115.2(6) . . ?
C7 C8 H8A 108.5 . . ?
C8A C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
C8A C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
O1 C8A N4 102.2(5) . . ?
O1 C8A C8 109.9(6) . . ?
N4 C8A C8 107.0(5) . . ?
O1 C8A C15 111.6(5) . . ?
N4 C8A C15 112.0(5) . . ?
C8 C8A C15 113.4(6) . . ?
C14 C9 C10 117.0(6) . . ?
C14 C9 C3 120.0(6) . . ?
C10 C9 C3 122.9(6) . . ?
C11 C10 C9 121.0(6) . . ?
C11 C10 H10A 119.5 . . ?
C9 C10 H10A 119.5 . . ?
C10 C11 C12 119.2(7) . . ?
C10 C11 H11A 120.4 . . ?
C12 C11 H11A 120.4 . . ?
C13 C12 C11 120.9(7) . . ?
C13 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C12 C13 C14 119.8(7) . . ?
C12 C13 H13A 120.1 . . ?
C14 C13 H13A 120.1 . . ?
C13 C14 C9 122.2(7) . . ?
C13 C14 H14A 118.9 . . ?
C9 C14 H14A 118.9 . . ?
C8A C15 H15A 109.5 . . ?
C8A C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8A C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C22 O21 C28A 105.6(4) . . ?
O21 C22 C23 105.5(5) . . ?
O21 C22 H22A 110.6 . . ?
C23 C22 H22A 110.6 . . ?
O21 C22 H22B 110.6 . . ?
C23 C22 H22B 110.6 . . ?
H22A C22 H22B 108.8 . . ?
N24 C23 C29 112.7(5) . . ?
N24 C23 C22 100.3(5) . . ?
C29 C23 C22 112.4(6) . . ?
N24 C23 H23A 110.3 . . ?
C29 C23 H23A 110.3 . . ?
C22 C23 H23A 110.3 . . ?
C25 N24 C23 122.6(5) . . ?
C25 N24 C28A 125.6(5) . . ?
C23 N24 C28A 111.3(5) . . ?
O25 C25 N24 121.8(5) . . ?
O25 C25 C26 120.4(6) . . ?
N24 C25 C26 117.6(6) . . ?
C27 C26 C25 119.8(6) . . ?
C27 C26 H26A 107.4 . . ?
C25 C26 H26A 107.4 . . ?
C27 C26 H26B 107.4 . . ?
C25 C26 H26B 107.4 . . ?
H26A C26 H26B 106.9 . . ?
O27 C27 C26 103.6(7) . . ?
O27 C27 C28 110.1(6) . . ?
C26 C27 C28 115.6(6) . . ?
O27 C27 H27A 109.1 . . ?
C26 C27 H27A 109.1 . . ?
C28 C27 H27A 109.1 . . ?
C27 O27 H27 109.5 . . ?
C27 C28 C28A 113.7(5) . . ?
C27 C28 H28A 108.8 . . ?
C28A C28 H28A 108.8 . . ?
C27 C28 H28B 108.8 . . ?
C28A C28 H28B 108.8 . . ?
H28A C28 H28B 107.7 . . ?
O21 C28A N24 102.1(5) . . ?
O21 C28A C28 109.3(5) . . ?
N24 C28A C28 109.7(5) . . ?
O21 C28A C35 109.8(5) . . ?
N24 C28A C35 111.6(5) . . ?
C28 C28A C35 113.7(5) . . ?
C30 C29 C34 118.4(7) . . ?
C30 C29 C23 121.0(7) . . ?
C34 C29 C23 120.5(7) . . ?
C29 C30 C31 121.7(8) . . ?
C29 C30 H30A 119.1 . . ?
C31 C30 H30A 119.1 . . ?
C32 C31 C30 119.2(9) . . ?
C32 C31 H31A 120.4 . . ?
C30 C31 H31A 120.4 . . ?
C31 C32 C33 120.1(10) . . ?
C31 C32 H32A 119.9 . . ?
C33 C32 H32A 119.9 . . ?
C32 C33 C34 119.8(9) . . ?
C32 C33 H33A 120.1 . . ?
C34 C33 H33A 120.1 . . ?
C29 C34 C33 120.7(8) . . ?
C29 C34 H34A 119.7 . . ?
C33 C34 H34A 119.7 . . ?
C28A C35 H35A 109.5 . . ?
C28A C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C28A C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 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
C8A O1 C2 C3 -42.2(6) . . . . ?
O1 C2 C3 N4 28.4(6) . . . . ?
O1 C2 C3 C9 -93.9(7) . . . . ?
C9 C3 N4 C5 -64.1(7) . . . . ?
C2 C3 N4 C5 175.8(5) . . . . ?
C9 C3 N4 C8A 113.9(6) . . . . ?
C2 C3 N4 C8A -6.3(6) . . . . ?
C3 N4 C5 O5 -5.7(9) . . . . ?
C8A N4 C5 O5 176.6(5) . . . . ?
C3 N4 C5 C6 175.9(5) . . . . ?
C8A N4 C5 C6 -1.8(8) . . . . ?
O5 C5 C6 C7 146.7(6) . . . . ?
N4 C5 C6 C7 -34.9(8) . . . . ?
C5 C6 C7 O7 148.4(6) . . . . ?
C5 C6 C7 C8 24.3(8) . . . . ?
O7 C7 C8 C8A -101.2(7) . . . . ?
C6 C7 C8 C8A 20.0(8) . . . . ?
C2 O1 C8A N4 36.9(6) . . . . ?
C2 O1 C8A C8 150.2(5) . . . . ?
C2 O1 C8A C15 -83.0(6) . . . . ?
C5 N4 C8A O1 160.2(5) . . . . ?
C3 N4 C8A O1 -17.8(6) . . . . ?
C5 N4 C8A C8 44.7(7) . . . . ?
C3 N4 C8A C8 -133.3(5) . . . . ?
C5 N4 C8A C15 -80.2(7) . . . . ?
C3 N4 C8A C15 101.8(6) . . . . ?
C7 C8 C8A O1 -162.0(5) . . . . ?
C7 C8 C8A N4 -51.9(7) . . . . ?
C7 C8 C8A C15 72.2(7) . . . . ?
N4 C3 C9 C14 147.7(6) . . . . ?
C2 C3 C9 C14 -99.9(7) . . . . ?
N4 C3 C9 C10 -36.8(8) . . . . ?
C2 C3 C9 C10 75.6(7) . . . . ?
C14 C9 C10 C11 0.3(8) . . . . ?
C3 C9 C10 C11 -175.3(6) . . . . ?
C9 C10 C11 C12 -0.4(9) . . . . ?
C10 C11 C12 C13 -0.2(10) . . . . ?
C11 C12 C13 C14 1.0(11) . . . . ?
C12 C13 C14 C9 -1.1(10) . . . . ?
C10 C9 C14 C13 0.5(9) . . . . ?
C3 C9 C14 C13 176.2(5) . . . . ?
C28A O21 C22 C23 -39.1(6) . . . . ?
O21 C22 C23 N24 23.7(6) . . . . ?
O21 C22 C23 C29 -96.3(6) . . . . ?
C29 C23 N24 C25 -53.1(8) . . . . ?
C22 C23 N24 C25 -172.9(5) . . . . ?
C29 C23 N24 C28A 119.0(6) . . . . ?
C22 C23 N24 C28A -0.8(6) . . . . ?
C23 N24 C25 O25 -11.4(9) . . . . ?
C28A N24 C25 O25 177.7(6) . . . . ?
C23 N24 C25 C26 163.9(6) . . . . ?
C28A N24 C25 C26 -7.1(9) . . . . ?
O25 C25 C26 C27 169.9(7) . . . . ?
N24 C25 C26 C27 -5.5(10) . . . . ?
C25 C26 C27 O27 108.7(8) . . . . ?
C25 C26 C27 C28 -11.8(11) . . . . ?
O27 C27 C28 C28A -77.2(8) . . . . ?
C26 C27 C28 C28A 39.6(9) . . . . ?
C22 O21 C28A N24 37.1(5) . . . . ?
C22 O21 C28A C28 153.3(5) . . . . ?
C22 O21 C28A C35 -81.4(6) . . . . ?
C25 N24 C28A O21 150.0(6) . . . . ?
C23 N24 C28A O21 -21.9(6) . . . . ?
C25 N24 C28A C28 34.1(8) . . . . ?
C23 N24 C28A C28 -137.8(5) . . . . ?
C25 N24 C28A C35 -92.8(7) . . . . ?
C23 N24 C28A C35 95.3(6) . . . . ?
C27 C28 C28A O21 -160.0(5) . . . . ?
C27 C28 C28A N24 -48.8(8) . . . . ?
C27 C28 C28A C35 76.9(7) . . . . ?
N24 C23 C29 C30 -46.1(9) . . . . ?
C22 C23 C29 C30 66.4(8) . . . . ?
N24 C23 C29 C34 137.4(6) . . . . ?
C22 C23 C29 C34 -110.1(7) . . . . ?
C34 C29 C30 C31 1.4(11) . . . . ?
C23 C29 C30 C31 -175.2(6) . . . . ?
C29 C30 C31 C32 0.8(13) . . . . ?
C30 C31 C32 C33 -1.6(14) . . . . ?
C31 C32 C33 C34 0.3(15) . . . . ?
C30 C29 C34 C33 -2.6(10) . . . . ?
C23 C29 C34 C33 174.0(6) . . . . ?
C32 C33 C34 C29 1.8(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O7 H7 O25 0.82 2.02 2.744(6) 147.7 . yes
O27 H27 O5 0.82 2.23 2.944(7) 145.0 2_656 yes

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_38
_database_code_depnum_ccdc_archive 'CCDC 2125371'
loop_
_audit_author_name
_audit_author_address
'Sylvain Bernes'
;Instituto de Fisica, BUAP, Puebla
Mexico
;
_audit_update_record             
;
2021-11-30 deposited with the CCDC.	2022-01-21 downloaded from the CCDC.
;

# Clave Lab.  :  ENR500
# Clave IF-UAP:  ENR500
# Solicitud: 482
# Firma en la Solicitud: La solicitud no fue firmada 
# Clave datos : ... \BUAP\Sylvain\ENR500\50mm_1\

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_audit_creation_date             2021-10-14

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          369
_chemical_formula_moiety         'C7 H14 N O3, Cl, H2 O'
_chemical_formula_sum            'C7 H16 Cl N O4'
_chemical_formula_weight         213.66
_chemical_absolute_configuration ad
_chemical_optical_rotation       ?

_chemical_properties_physical    ?
_chemical_properties_biological  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0013 0.0009 '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'
Cl Cl 0.1009 0.0992 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0058 0.0036 '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       ?

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                   8.2312(5)
_cell_length_b                   9.1140(9)
_cell_length_c                   13.9693(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1047.97(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    17116
_cell_measurement_theta_min      2.11
_cell_measurement_theta_max      23.84

_exptl_crystal_recrystallization_method 
;
Re-crystallisation from solvent: Methanol/AcOEt
;

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.046
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 3 -2 0.0110
-5 -3 2 0.0350
-3 2 6 0.2030
3 -2 -6 0.2390
-2 -9 3 0.0420
1 7 -2 0.0510

_exptl_absorpt_coefficient_mu    0.185
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2094
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'X-AREA 1.88 (Stoe & Cie, 2019)'

_diffrn_ambient_temperature      295(1)
_diffrn_ambient_environment      air
_diffrn_measurement_specimen_support Mitegen
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_diffrn_source_current           0.600
_diffrn_source_power             0.039
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
1545 frames, 100-140 s/frame, 1 deg./frame, detector distance = 50 mm
;
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            29183
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0792
_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       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.105
_diffrn_reflns_theta_max         20.990
_diffrn_reflns_theta_full        19.664
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2273
_reflns_number_gt                1768
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.992

_reflns_special_details          ?

_computing_data_collection       'X-AREA 1.88 (Stoe & Cie, 2019)'
_computing_cell_refinement       'X-AREA 1.88'
_computing_data_reduction        'X-AREA 1.88'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'

_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)+(0.0247P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 625 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_number_reflns         2273
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0531
_refine_ls_wR_factor_gt          0.0501
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_restrained_S_all      0.877
_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
Cl1 Cl 0.38116(6) -0.00930(7) 0.42282(4) 0.04655(17) Uani 1 1 d . . . . .
N1 N 0.2581(2) 0.3204(2) 0.37246(14) 0.0357(4) Uani 1 1 d . . . . .
H1A H 0.139(3) 0.307(3) 0.3712(18) 0.054 Uiso 1 1 d . U . . .
H1B H 0.300(3) 0.231(3) 0.3885(19) 0.054 Uiso 1 1 d . U . . .
C2 C 0.3004(2) 0.4344(2) 0.44583(16) 0.0349(5) Uani 1 1 d . . . . .
H2A H 0.244253 0.408829 0.505395 0.042 Uiso 1 1 calc R U . . .
C3 C 0.2394(3) 0.5844(2) 0.41395(17) 0.0364(5) Uani 1 1 d . . . . .
H3A H 0.121544 0.584797 0.414305 0.044 Uiso 1 1 calc R U . . .
H3B H 0.276490 0.658430 0.458795 0.044 Uiso 1 1 calc R U . . .
C4 C 0.2998(3) 0.6221(3) 0.31433(18) 0.0409(6) Uani 1 1 d . . . . .
H4 H 0.418753 0.627142 0.315109 0.049 Uiso 1 1 calc R U . . .
C5 C 0.2469(3) 0.5065(3) 0.24332(15) 0.0432(5) Uani 1 1 d . . . . .
H5A H 0.288429 0.531594 0.180425 0.052 Uiso 1 1 calc R U . . .
H5B H 0.129263 0.505389 0.239740 0.052 Uiso 1 1 calc R U . . .
C6 C 0.3070(3) 0.3547(3) 0.27073(17) 0.0405(6) Uani 1 1 d . . . . .
H6 H 0.425862 0.353965 0.266799 0.049 Uiso 1 1 calc R U . . .
C7 C 0.4820(3) 0.4293(3) 0.46516(17) 0.0395(6) Uani 1 1 d . . . . .
C8 C 0.2409(3) 0.2345(3) 0.2056(2) 0.0575(7) Uani 1 1 d . . . . .
H8A H 0.273358 0.140388 0.229729 0.086 Uiso 1 1 calc R U . . .
H8B H 0.283279 0.247500 0.142116 0.086 Uiso 1 1 calc R U . . .
H8C H 0.124476 0.240072 0.203879 0.086 Uiso 1 1 calc R U . . .
O1 O 0.57299(17) 0.3399(2) 0.43163(13) 0.0539(5) Uani 1 1 d . . . . .
O2 O 0.5243(2) 0.5342(2) 0.52569(14) 0.0589(5) Uani 1 1 d . . . . .
H2 H 0.627(4) 0.523(4) 0.537(2) 0.088 Uiso 1 1 d . U . . .
O3 O 0.2363(2) 0.7597(2) 0.28354(13) 0.0559(5) Uani 1 1 d . . . . .
H3 H 0.278(4) 0.832(4) 0.317(2) 0.084 Uiso 1 1 d . U . . .
O4 O -0.07173(19) 0.3146(3) 0.38125(16) 0.0619(6) Uani 1 1 d . . . . .
H4A H -0.118(4) 0.380(4) 0.415(3) 0.093 Uiso 1 1 d . U . . .
H4B H -0.131(4) 0.306(4) 0.333(3) 0.093 Uiso 1 1 d . U . . .


_geom_special_details            ?

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.500(3) . ?
N1 C6 1.510(3) . ?
N1 H1A 0.99(3) . ?
N1 H1B 0.91(3) . ?
C2 C7 1.519(3) . ?
C2 C3 1.523(3) . ?
C2 H2A 0.9800 . ?
C3 C4 1.517(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O3 1.425(3) . ?
C4 C5 1.511(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.518(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C8 1.524(3) . ?
C6 H6 0.9800 . ?
C7 O1 1.202(3) . ?
C7 O2 1.323(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
O2 H2 0.87(3) . ?
O3 H3 0.87(3) . ?
O4 H4A 0.85(4) . ?
O4 H4B 0.83(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 115.95(18) . . ?
C2 N1 H1A 109.1(14) . . ?
C6 N1 H1A 105.9(15) . . ?
C2 N1 H1B 111.3(17) . . ?
C6 N1 H1B 108.4(17) . . ?
H1A N1 H1B 106(2) . . ?
N1 C2 C7 109.20(19) . . ?
N1 C2 C3 110.18(17) . . ?
C7 C2 C3 113.82(19) . . ?
N1 C2 H2A 107.8 . . ?
C7 C2 H2A 107.8 . . ?
C3 C2 H2A 107.8 . . ?
C4 C3 C2 111.29(18) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O3 C4 C5 108.0(2) . . ?
O3 C4 C3 110.8(2) . . ?
C5 C4 C3 110.5(2) . . ?
O3 C4 H4 109.1 . . ?
C5 C4 H4 109.1 . . ?
C3 C4 H4 109.1 . . ?
C4 C5 C6 112.07(18) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N1 C6 C5 109.83(19) . . ?
N1 C6 C8 108.5(2) . . ?
C5 C6 C8 112.8(2) . . ?
N1 C6 H6 108.5 . . ?
C5 C6 H6 108.5 . . ?
C8 C6 H6 108.5 . . ?
O1 C7 O2 125.1(2) . . ?
O1 C7 C2 124.4(2) . . ?
O2 C7 C2 110.5(2) . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 O2 H2 107(2) . . ?
C4 O3 H3 111(2) . . ?
H4A O4 H4B 105(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C7 -74.1(2) . . . . ?
C6 N1 C2 C3 51.6(2) . . . . ?
N1 C2 C3 C4 -53.6(2) . . . . ?
C7 C2 C3 C4 69.4(2) . . . . ?
C2 C3 C4 O3 177.48(18) . . . . ?
C2 C3 C4 C5 57.7(2) . . . . ?
O3 C4 C5 C6 -179.22(19) . . . . ?
C3 C4 C5 C6 -57.8(2) . . . . ?
C2 N1 C6 C5 -51.1(2) . . . . ?
C2 N1 C6 C8 -174.87(19) . . . . ?
C4 C5 C6 N1 53.0(2) . . . . ?
C4 C5 C6 C8 174.3(2) . . . . ?
N1 C2 C7 O1 -5.1(3) . . . . ?
C3 C2 C7 O1 -128.7(3) . . . . ?
N1 C2 C7 O2 176.50(19) . . . . ?
C3 C2 C7 O2 52.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4A Cl1 0.85(4) 2.55(4) 3.285(2) 145(3) 4_456 yes
O4 H4A O1 0.85(4) 2.58(3) 3.017(2) 113(3) 1_455 yes
N1 H1A O4 0.99(3) 1.74(3) 2.718(3) 169(2) . yes
N1 H1B Cl1 0.91(3) 2.34(3) 3.249(2) 174(2) . yes
O2 H2 Cl1 0.87(3) 2.17(3) 3.0326(18) 175(3) 4_556 yes
O3 H3 Cl1 0.87(3) 2.24(4) 3.105(2) 170(3) 1_565 yes
O4 H4B O3 0.83(4) 1.90(4) 2.718(3) 169(3) 3_545 yes

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.103
_refine_diff_density_rms         0.029

####################################################################### 
# 
# 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_33a
_database_code_depnum_ccdc_archive 'CCDC 2125370'
loop_
_audit_author_name
_audit_author_address
'Sylvain Bernes'
;Instituto de Fisica, BUAP, Puebla
Mexico
;
_audit_update_record             
;
2021-11-30 deposited with the CCDC.	2022-01-21 downloaded from the CCDC.
;

# Clave Lab.  :  ENR-356-1
# Clave IF-UAP:  ENR_356_1
# Solicitud: 336
# Firma en la Solicitud: Dr. David Aparicio (ICUAP)
# Clave datos : ... \BUAP\Sylvain\ENR_356_1\40mm_1\

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_audit_creation_date             2019-06-07

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 N O2'
_chemical_formula_sum            'C14 H21 N O2'
_chemical_formula_weight         235.32
_chemical_absolute_configuration syn
_chemical_optical_rotation       ?

_chemical_properties_physical    ?
_chemical_properties_biological  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 '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       ?

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                   7.0341(8)
_cell_length_b                   14.022(2)
_cell_length_c                   14.321(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1412.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    6607
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      21.51

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.034
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 4 3 0.0220
-3 -5 -4 0.0120
0 -1 1 0.0310
0 6 -5 0.0320
-3 5 7 0.2220
1 -2 -2 0.2190

_exptl_absorpt_coefficient_mu    0.047
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1182
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'X-AREA 1.86 (Stoe & Cie, 2018)'

_diffrn_ambient_temperature      295(1)
_diffrn_ambient_environment      air
_diffrn_measurement_specimen_support Mitegen
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_diffrn_source_current           0.600
_diffrn_source_power             0.039
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
1127 frames, 80 s/frame, 1 deg./frame, detector distance = 40 mm
;
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            30320
_diffrn_reflns_av_unetI/netI     0.1422
_diffrn_reflns_av_R_equivalents  0.1988
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.546
_diffrn_reflns_theta_max         20.499
_diffrn_reflns_theta_full        19.664
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2885
_reflns_number_gt                1087
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          ?

_computing_data_collection       'X-AREA 1.86 (Stoe & Cie, 2018)'
_computing_cell_refinement       'X-AREA 1.86'
_computing_data_reduction        'X-AREA 1.86'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'

_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)+(0.0219P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ? # -0.2(10)
_refine_ls_number_reflns         2885
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1343
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0736
_refine_ls_wR_factor_gt          0.0593
_refine_ls_goodness_of_fit_ref   0.681
_refine_ls_restrained_S_all      0.681
_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
N1 N 0.3673(3) 0.5729(2) 0.30187(19) 0.0403(8) Uani 1 1 d . . . . .
C2 C 0.5080(5) 0.5088(2) 0.2574(3) 0.0468(10) Uani 1 1 d . . . . .
H2A H 0.448490 0.476104 0.204391 0.056 Uiso 1 1 calc R U . . .
C3 C 0.5683(4) 0.4348(3) 0.3305(3) 0.0510(10) Uani 1 1 d . . . . .
H3A H 0.661123 0.391931 0.303260 0.061 Uiso 1 1 calc R U . . .
H3B H 0.628012 0.467163 0.382716 0.061 Uiso 1 1 calc R U . . .
C4 C 0.4016(5) 0.3781(3) 0.3653(3) 0.0529(11) Uani 1 1 d . . . . .
H4A H 0.347773 0.341213 0.313499 0.064 Uiso 1 1 calc R U . . .
O4 O 0.4573(4) 0.3138(2) 0.4391(2) 0.0733(10) Uani 1 1 d . . . . .
H4 H 0.548(6) 0.288(3) 0.430(3) 0.110 Uiso 1 1 d . U . . .
C5 C 0.2506(5) 0.4442(3) 0.4042(3) 0.0526(11) Uani 1 1 d . . . . .
H5A H 0.297860 0.475351 0.460038 0.063 Uiso 1 1 calc R U . . .
H5B H 0.138441 0.407693 0.420956 0.063 Uiso 1 1 calc R U . . .
C6 C 0.1989(4) 0.5190(2) 0.3308(3) 0.0495(11) Uani 1 1 d . . . . .
H6A H 0.143349 0.487814 0.276866 0.059 Uiso 1 1 calc R U . . .
H6B H 0.105079 0.562489 0.356365 0.059 Uiso 1 1 calc R U . . .
C7 C 0.3181(5) 0.6595(3) 0.2480(2) 0.0425(10) Uani 1 1 d . . . . .
H7A H 0.439063 0.686651 0.226943 0.051 Uiso 1 1 calc R U . . .
C8 C 0.2042(5) 0.6397(3) 0.1606(3) 0.0543(11) Uani 1 1 d . . . . .
H8A H 0.257716 0.585684 0.127452 0.065 Uiso 1 1 calc R U . . .
H8B H 0.073699 0.624675 0.176866 0.065 Uiso 1 1 calc R U . . .
O8 O 0.2098(4) 0.7233(2) 0.10245(18) 0.0608(9) Uani 1 1 d . . . . .
H8 H 0.171(7) 0.716(3) 0.061(3) 0.091 Uiso 1 1 d . U . . .
C9 C 0.6831(4) 0.5630(3) 0.2235(3) 0.0773(15) Uani 1 1 d . . . . .
H9A H 0.649501 0.601781 0.170753 0.116 Uiso 1 1 calc R U . . .
H9B H 0.779997 0.518379 0.205490 0.116 Uiso 1 1 calc R U . . .
H9C H 0.730032 0.602897 0.272818 0.116 Uiso 1 1 calc R U . . .
C10 C 0.2313(5) 0.7325(3) 0.3132(3) 0.0484(10) Uani 1 1 d . . . . .
C11 C 0.3436(6) 0.7665(3) 0.3846(3) 0.0745(14) Uani 1 1 d . . . . .
H11A H 0.467702 0.744484 0.390511 0.089 Uiso 1 1 calc R U . . .
C12 C 0.2737(10) 0.8340(4) 0.4486(4) 0.108(2) Uani 1 1 d . . . . .
H12A H 0.350444 0.856992 0.496417 0.130 Uiso 1 1 calc R U . . .
C13 C 0.0904(11) 0.8650(4) 0.4390(4) 0.113(2) Uani 1 1 d . . . . .
H13A H 0.042007 0.909121 0.481301 0.135 Uiso 1 1 calc R U . . .
C14 C -0.0208(7) 0.8329(4) 0.3696(4) 0.0916(17) Uani 1 1 d . . . . .
H14A H -0.145052 0.854975 0.364357 0.110 Uiso 1 1 calc R U . . .
C15 C 0.0479(6) 0.7671(3) 0.3056(3) 0.0666(12) Uani 1 1 d . . . . .
H15A H -0.029836 0.746161 0.257203 0.080 Uiso 1 1 calc R U . . .


_geom_special_details            ?

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.464(4) . ?
N1 C7 1.479(4) . ?
N1 C2 1.481(4) . ?
C2 C9 1.527(4) . ?
C2 C3 1.533(5) . ?
C2 H2A 0.9800 . ?
C3 C4 1.502(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O4 1.443(4) . ?
C4 C5 1.516(4) . ?
C4 H4A 0.9800 . ?
O4 H4 0.75(4) . ?
C5 C6 1.530(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.512(4) . ?
C7 C10 1.515(5) . ?
C7 H7A 0.9800 . ?
C8 O8 1.438(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
O8 H8 0.66(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.376(5) . ?
C10 C15 1.383(4) . ?
C11 C12 1.406(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.367(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.343(7) . ?
C13 H13A 0.9300 . ?
C14 C15 1.388(5) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C7 112.4(2) . . ?
C6 N1 C2 110.4(3) . . ?
C7 N1 C2 115.5(3) . . ?
N1 C2 C9 111.9(3) . . ?
N1 C2 C3 107.5(3) . . ?
C9 C2 C3 109.3(3) . . ?
N1 C2 H2A 109.3 . . ?
C9 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C4 C3 C2 111.7(3) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
O4 C4 C3 111.2(3) . . ?
O4 C4 C5 107.6(3) . . ?
C3 C4 C5 110.2(3) . . ?
O4 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C4 O4 H4 114(4) . . ?
C4 C5 C6 109.5(3) . . ?
C4 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
N1 C6 C5 110.9(3) . . ?
N1 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
N1 C7 C8 113.9(3) . . ?
N1 C7 C10 109.1(3) . . ?
C8 C7 C10 114.9(3) . . ?
N1 C7 H7A 106.1 . . ?
C8 C7 H7A 106.1 . . ?
C10 C7 H7A 106.1 . . ?
O8 C8 C7 108.4(3) . . ?
O8 C8 H8A 110.0 . . ?
C7 C8 H8A 110.0 . . ?
O8 C8 H8B 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
C8 O8 H8 113(4) . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 118.2(4) . . ?
C11 C10 C7 117.4(3) . . ?
C15 C10 C7 124.3(4) . . ?
C10 C11 C12 121.1(5) . . ?
C10 C11 H11A 119.5 . . ?
C12 C11 H11A 119.5 . . ?
C13 C12 C11 118.6(6) . . ?
C13 C12 H12A 120.7 . . ?
C11 C12 H12A 120.7 . . ?
C14 C13 C12 121.1(6) . . ?
C14 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
C13 C14 C15 120.6(5) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C10 C15 C14 120.4(4) . . ?
C10 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C9 178.2(3) . . . . ?
C7 N1 C2 C9 49.3(4) . . . . ?
C6 N1 C2 C3 -61.7(4) . . . . ?
C7 N1 C2 C3 169.3(3) . . . . ?
N1 C2 C3 C4 59.2(4) . . . . ?
C9 C2 C3 C4 -179.1(3) . . . . ?
C2 C3 C4 O4 -175.6(3) . . . . ?
C2 C3 C4 C5 -56.4(4) . . . . ?
O4 C4 C5 C6 175.3(3) . . . . ?
C3 C4 C5 C6 53.9(4) . . . . ?
C7 N1 C6 C5 -166.9(3) . . . . ?
C2 N1 C6 C5 62.5(4) . . . . ?
C4 C5 C6 N1 -57.4(4) . . . . ?
C6 N1 C7 C8 -58.3(4) . . . . ?
C2 N1 C7 C8 69.6(4) . . . . ?
C6 N1 C7 C10 71.5(4) . . . . ?
C2 N1 C7 C10 -160.5(3) . . . . ?
N1 C7 C8 O8 -164.6(3) . . . . ?
C10 C7 C8 O8 68.5(4) . . . . ?
N1 C7 C10 C11 62.4(4) . . . . ?
C8 C7 C10 C11 -168.2(3) . . . . ?
N1 C7 C10 C15 -117.7(4) . . . . ?
C8 C7 C10 C15 11.6(5) . . . . ?
C15 C10 C11 C12 0.6(6) . . . . ?
C7 C10 C11 C12 -179.6(4) . . . . ?
C10 C11 C12 C13 0.4(8) . . . . ?
C11 C12 C13 C14 -0.7(9) . . . . ?
C12 C13 C14 C15 0.0(9) . . . . ?
C11 C10 C15 C14 -1.3(6) . . . . ?
C7 C10 C15 C14 178.9(4) . . . . ?
C13 C14 C15 C10 1.0(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4 O8 0.75(4) 1.98(4) 2.729(4) 176(5) 3_645 yes
O8 H8 O4 0.66(4) 2.01(4) 2.669(4) 176(6) 2_564 yes

_refine_diff_density_max         0.111
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.027

####################################################################### 
# 
# 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_29
_database_code_depnum_ccdc_archive 'CCDC 2125368'
loop_
_audit_author_name
_audit_author_address
'Sylvain Bernes'
;Instituto de Fisica, BUAP, Puebla
Mexico
;
_audit_update_record             
;
2021-11-30 deposited with the CCDC.	2022-01-21 downloaded from the CCDC.
;

# Clave Lab.  :  ENR157_1
# Clave IF-UAP:  ENR157_1
# Solicitud: 124
# Firma en la Solicitud: Dr. Joel L. Teran (ICUAP)
# Clave datos : ... \BUAP\Sylvain\ENR157_1\40mm_2\

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_audit_creation_date             2018-06-25

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 N O3'
_chemical_formula_sum            'C14 H15 N O3'
_chemical_formula_weight         245.27
_chemical_absolute_configuration syn
_chemical_optical_rotation       ?

_chemical_properties_physical    ?
_chemical_properties_biological  ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 '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       ?

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                   7.4810(4)
_cell_length_b                   10.4640(9)
_cell_length_c                   15.9980(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1252.34(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    18729
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      24.84

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.057
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4137
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'X-AREA 1.82 (Stoe & Cie, 2018)'

_diffrn_ambient_temperature      295(1)
_diffrn_ambient_environment      air
_diffrn_measurement_specimen_support Mitegen
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_diffrn_source_current           0.600
_diffrn_source_power             0.039
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
1400 frames, 20 s/frame, 1 deg./frame, detector distance = 40 mm
;
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            40682
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.372
_diffrn_reflns_theta_max         22.494
_diffrn_reflns_theta_full        19.664
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3318
_reflns_number_gt                1955
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          ?

_computing_data_collection       'X-AREA 1.82 (Stoe & Cie, 2018)'
_computing_cell_refinement       'X-AREA 1.82'
_computing_data_reduction        'X-AREA 1.82'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'

_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)+(0.0439P)²] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ? # 0.7(9)
_refine_ls_number_reflns         3318
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0762
_refine_ls_goodness_of_fit_ref   0.813
_refine_ls_restrained_S_all      0.813
_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 0.08851(17) 0.57286(15) 0.25693(10) 0.0574(4) Uani 1 1 d . . . . .
C2 C 0.2499(3) 0.5008(2) 0.24310(16) 0.0553(6) Uani 1 1 d . . . . .
H2A H 0.264449 0.480864 0.184277 0.066 Uiso 1 1 calc R U . . .
H2B H 0.248204 0.421696 0.274710 0.066 Uiso 1 1 calc R U . . .
C3 C 0.4003(3) 0.5889(2) 0.27367(13) 0.0465(5) Uani 1 1 d . . . . .
H3A H 0.492397 0.538326 0.302012 0.056 Uiso 1 1 calc R U . . .
N4 N 0.30251(19) 0.66624(18) 0.33505(11) 0.0438(4) Uani 1 1 d . . . . .
C5 C 0.3777(3) 0.7541(2) 0.38439(12) 0.0470(5) Uani 1 1 d . . . . .
O2 O 0.53935(19) 0.77441(18) 0.38523(10) 0.0644(5) Uani 1 1 d . . . . .
C6 C 0.2502(3) 0.8283(2) 0.43897(14) 0.0524(6) Uani 1 1 d . . . . .
H6A H 0.299513 0.913040 0.447343 0.063 Uiso 1 1 calc R U . . .
H6B H 0.245819 0.786941 0.493204 0.063 Uiso 1 1 calc R U . . .
C7 C 0.0610(3) 0.8428(2) 0.40766(14) 0.0496(5) Uani 1 1 d . . . . .
O3 O -0.0367(2) 0.92196(18) 0.43823(11) 0.0730(5) Uani 1 1 d . . . . .
C8 C 0.0028(2) 0.7566(2) 0.33744(15) 0.0522(6) Uani 1 1 d . . . . .
H8A H 0.017167 0.801141 0.284679 0.063 Uiso 1 1 calc R U . . .
H8B H -0.122934 0.736369 0.344085 0.063 Uiso 1 1 calc R U . . .
C8A C 0.1096(2) 0.6341(2) 0.33538(14) 0.0480(5) Uani 1 1 d . . . . .
C9 C 0.4837(2) 0.6654(2) 0.20363(13) 0.0453(5) Uani 1 1 d . . . . .
C10 C 0.3881(3) 0.7582(2) 0.16074(15) 0.0591(6) Uani 1 1 d . . . . .
H10A H 0.273985 0.780545 0.178650 0.071 Uiso 1 1 calc R U . . .
C11 C 0.4611(4) 0.8178(3) 0.09171(16) 0.0711(7) Uani 1 1 d . . . . .
H11A H 0.396295 0.880390 0.063724 0.085 Uiso 1 1 calc R U . . .
C12 C 0.6278(4) 0.7853(3) 0.06427(16) 0.0767(8) Uani 1 1 d . . . . .
H12A H 0.675139 0.823484 0.016684 0.092 Uiso 1 1 calc R U . . .
C13 C 0.7250(4) 0.6958(3) 0.10741(18) 0.0746(8) Uani 1 1 d . . . . .
H13A H 0.839684 0.674878 0.089604 0.090 Uiso 1 1 calc R U . . .
C14 C 0.6541(3) 0.6365(2) 0.17709(15) 0.0574(6) Uani 1 1 d . . . . .
H14A H 0.721793 0.576709 0.206218 0.069 Uiso 1 1 calc R U . . .
C15 C 0.0610(3) 0.5451(2) 0.40656(17) 0.0679(7) Uani 1 1 d . . . . .
H15A H 0.128881 0.467565 0.401829 0.102 Uiso 1 1 calc R U . . .
H15B H -0.064242 0.525618 0.404053 0.102 Uiso 1 1 calc R U . . .
H15C H 0.087696 0.585740 0.458898 0.102 Uiso 1 1 calc R U . . .


_geom_special_details            ?

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 C8A 1.418(3) . ?
O1 C2 1.440(3) . ?
C2 C3 1.535(3) . ?
C3 N4 1.468(3) . ?
C3 C9 1.512(3) . ?
N4 C5 1.336(3) . ?
N4 C8A 1.482(2) . ?
C5 O2 1.228(2) . ?
C5 C6 1.508(3) . ?
C6 C7 1.509(3) . ?
C7 O3 1.208(3) . ?
C7 C8 1.505(3) . ?
C8 C8A 1.511(3) . ?
C8A C15 1.515(3) . ?
C9 C14 1.377(3) . ?
C9 C10 1.388(3) . ?
C10 C11 1.381(3) . ?
C11 C12 1.365(4) . ?
C12 C13 1.372(4) . ?
C13 C14 1.382(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8A O1 C2 106.21(15) . . ?
O1 C2 C3 104.54(17) . . ?
N4 C3 C9 114.19(18) . . ?
N4 C3 C2 100.31(15) . . ?
C9 C3 C2 112.60(18) . . ?
C5 N4 C3 124.39(16) . . ?
C5 N4 C8A 124.35(17) . . ?
C3 N4 C8A 111.26(17) . . ?
O2 C5 N4 122.7(2) . . ?
O2 C5 C6 121.8(2) . . ?
N4 C5 C6 115.46(16) . . ?
C5 C6 C7 116.94(19) . . ?
O3 C7 C8 122.6(2) . . ?
O3 C7 C6 120.2(2) . . ?
C8 C7 C6 117.29(19) . . ?
C7 C8 C8A 111.82(17) . . ?
O1 C8A N4 102.00(15) . . ?
O1 C8A C8 110.11(18) . . ?
N4 C8A C8 108.82(17) . . ?
O1 C8A C15 111.14(18) . . ?
N4 C8A C15 112.08(19) . . ?
C8 C8A C15 112.22(18) . . ?
C14 C9 C10 118.6(2) . . ?
C14 C9 C3 119.6(2) . . ?
C10 C9 C3 121.62(18) . . ?
C11 C10 C9 120.5(2) . . ?
C12 C11 C10 120.4(3) . . ?
C11 C12 C13 119.5(3) . . ?
C12 C13 C14 120.6(2) . . ?
C9 C14 C13 120.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8A O1 C2 C3 -40.6(2) . . . . ?
O1 C2 C3 N4 26.3(2) . . . . ?
O1 C2 C3 C9 -95.5(2) . . . . ?
C9 C3 N4 C5 -63.9(3) . . . . ?
C2 C3 N4 C5 175.5(2) . . . . ?
C9 C3 N4 C8A 116.26(19) . . . . ?
C2 C3 N4 C8A -4.4(2) . . . . ?
C3 N4 C5 O2 -3.2(4) . . . . ?
C8A N4 C5 O2 176.6(2) . . . . ?
C3 N4 C5 C6 176.26(19) . . . . ?
C8A N4 C5 C6 -3.9(3) . . . . ?
O2 C5 C6 C7 152.4(2) . . . . ?
N4 C5 C6 C7 -27.2(3) . . . . ?
C5 C6 C7 O3 -164.3(2) . . . . ?
C5 C6 C7 C8 15.0(3) . . . . ?
O3 C7 C8 C8A -155.2(2) . . . . ?
C6 C7 C8 C8A 25.5(3) . . . . ?
C2 O1 C8A N4 36.4(2) . . . . ?
C2 O1 C8A C8 151.81(17) . . . . ?
C2 O1 C8A C15 -83.2(2) . . . . ?
C5 N4 C8A O1 160.98(19) . . . . ?
C3 N4 C8A O1 -19.1(2) . . . . ?
C5 N4 C8A C8 44.6(3) . . . . ?
C3 N4 C8A C8 -135.48(18) . . . . ?
C5 N4 C8A C15 -80.1(3) . . . . ?
C3 N4 C8A C15 99.8(2) . . . . ?
C7 C8 C8A O1 -163.52(17) . . . . ?
C7 C8 C8A N4 -52.5(2) . . . . ?
C7 C8 C8A C15 72.1(2) . . . . ?
N4 C3 C9 C14 137.7(2) . . . . ?
C2 C3 C9 C14 -108.8(2) . . . . ?
N4 C3 C9 C10 -47.3(3) . . . . ?
C2 C3 C9 C10 66.3(3) . . . . ?
C14 C9 C10 C11 1.6(3) . . . . ?
C3 C9 C10 C11 -173.5(2) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C10 C11 C12 C13 -2.1(4) . . . . ?
C11 C12 C13 C14 1.5(4) . . . . ?
C10 C9 C14 C13 -2.3(3) . . . . ?
C3 C9 C14 C13 172.9(2) . . . . ?
C12 C13 C14 C9 0.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6B O2 0.97 2.57 3.399(3) 144.1 4_466 yes
C8 H8B O2 0.97 2.64 3.555(2) 157.2 1_455 yes

_refine_diff_density_max         0.130
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.027

