# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_CBZ-Cinnamicacid
_database_code_depnum_ccdc_archive 'CCDC 2225589'
loop_
_audit_author_name
_audit_author_address
'Ranjit Thakuria'
;Gauhati University
India
;
_audit_update_record             
;
2023-02-17 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_CBZ-Cinnamicacid    
;
PROBLEM: Hirshfeld Test Diff for    C4       --C5       .        9.0 s.u.
RESPONSE: The B-Alert for CBZ-CA maybe due to poor crystal quality and room temperature crystal data.
;
# Added during the CSD deposition process: Friday 17 February 2023 04:07 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 N2 O3'
_chemical_formula_weight         384.42

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

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

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

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

_cell_length_a                   15.3512(8)
_cell_length_b                   5.4506(3)
_cell_length_c                   23.7358(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.167(3)
_cell_angle_gamma                90
_cell_volume                     1974.56(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.37

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28915
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.065
_diffrn_reflns_theta_max         26.411
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4035
_reflns_number_gt                3418
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0782P)²+0.9370P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.069(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4035
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1579
_refine_ls_wR_factor_gt          0.1458
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.11395(10) 0.4658(3) 0.89246(7) 0.0385(4) Uani 1 1 d . . . . .
C2 C 0.05842(13) 0.2687(4) 0.87954(9) 0.0536(5) Uani 1 1 d . . . . .
H2 H 0.032393 0.189889 0.908181 0.064 Uiso 1 1 calc R U . . .
C3 C 0.04178(18) 0.1898(5) 0.82467(10) 0.0721(7) Uani 1 1 d . . . . .
H3 H 0.004886 0.056599 0.816054 0.086 Uiso 1 1 calc R U . . .
C4 C 0.07959(18) 0.3076(6) 0.78256(10) 0.0776(8) Uani 1 1 d . . . . .
H4 H 0.068795 0.252569 0.745379 0.093 Uiso 1 1 calc R U . . .
C5 C 0.13351(16) 0.5069(6) 0.79479(9) 0.0707(7) Uani 1 1 d . . . . .
H5 H 0.157116 0.587885 0.765456 0.085 Uiso 1 1 calc R U . . .
C6 C 0.15364(11) 0.5908(4) 0.85101(7) 0.0484(5) Uani 1 1 d . . . . .
C7 C 0.21353(13) 0.7945(4) 0.86426(10) 0.0619(6) Uani 1 1 d . . . . .
H7 H 0.213214 0.916771 0.836898 0.074 Uiso 1 1 calc R U . . .
C8 C 0.26888(13) 0.8271(4) 0.91097(10) 0.0621(6) Uani 1 1 d . . . . .
H8 H 0.301467 0.971263 0.913042 0.075 Uiso 1 1 calc R U . . .
C9 C 0.28365(11) 0.6607(4) 0.95905(8) 0.0455(4) Uani 1 1 d . . . . .
C10 C 0.36755(12) 0.6336(5) 0.98823(10) 0.0603(6) Uani 1 1 d . . . . .
H10 H 0.412547 0.736328 0.979479 0.072 Uiso 1 1 calc R U . . .
C11 C 0.38445(13) 0.4581(5) 1.02944(9) 0.0645(6) Uani 1 1 d . . . . .
H11 H 0.440707 0.442520 1.047966 0.077 Uiso 1 1 calc R U . . .
C12 C 0.31887(13) 0.3052(4) 1.04357(9) 0.0592(6) Uani 1 1 d . . . . .
H12 H 0.330959 0.183917 1.070851 0.071 Uiso 1 1 calc R U . . .
C13 C 0.23486(12) 0.3333(4) 1.01690(8) 0.0468(4) Uani 1 1 d . . . . .
H13 H 0.190055 0.231483 1.026389 0.056 Uiso 1 1 calc R U . . .
C14 C 0.21764(10) 0.5123(3) 0.97623(7) 0.0366(4) Uani 1 1 d . . . . .
C15 C 0.07525(9) 0.7070(3) 0.97299(6) 0.0322(3) Uani 1 1 d . . . . .
C16 C 0.36902(11) 0.0644(4) 0.77330(7) 0.0455(4) Uani 1 1 d . . . . .
C17 C 0.36909(13) 0.2575(4) 0.81064(9) 0.0556(5) Uani 1 1 d . . . . .
H17 H 0.325306 0.375784 0.805286 0.067 Uiso 1 1 calc R U . . .
C18 C 0.43314(15) 0.2787(4) 0.85599(9) 0.0607(5) Uani 1 1 d . . . . .
H18 H 0.431982 0.410423 0.880816 0.073 Uiso 1 1 calc R U . . .
C19 C 0.49830(14) 0.1068(4) 0.86454(8) 0.0581(5) Uani 1 1 d . . . . .
H19 H 0.541195 0.121170 0.895159 0.070 Uiso 1 1 calc R U . . .
C20 C 0.49996(14) -0.0871(4) 0.82762(9) 0.0595(5) Uani 1 1 d . . . . .
H20 H 0.544143 -0.204155 0.833106 0.071 Uiso 1 1 calc R U . . .
C21 C 0.43566(14) -0.1077(4) 0.78225(8) 0.0538(5) Uani 1 1 d . . . . .
H21 H 0.437184 -0.239125 0.757378 0.065 Uiso 1 1 calc R U . . .
C22 C 0.29773(13) 0.0494(4) 0.72667(8) 0.0539(5) Uani 1 1 d . . . . .
H22 H 0.257417 0.177332 0.724189 0.065 Uiso 1 1 calc R U . . .
C23 C 0.28465(14) -0.1211(4) 0.68875(9) 0.0589(5) Uani 1 1 d . . . . .
H23 H 0.323810 -0.251642 0.690019 0.071 Uiso 1 1 calc R U . . .
C24 C 0.20977(13) -0.1184(4) 0.64305(8) 0.0548(5) Uani 1 1 d . . . . .
H2A H -0.0349(14) 0.853(4) 0.9586(8) 0.049(5) Uiso 1 1 d . . . . .
H2B H -0.0234(13) 0.657(4) 0.9165(9) 0.048(6) Uiso 1 1 d . . . . .
H2C H 0.168(2) -0.286(6) 0.5715(14) 0.115(11) Uiso 1 1 d . . . . .
N1 N 0.12967(8) 0.5456(3) 0.94996(5) 0.0347(3) Uani 1 1 d . . . . .
N2 N -0.00450(9) 0.7412(3) 0.94533(7) 0.0411(4) Uani 1 1 d . . . . .
O1 O 0.09853(7) 0.8170(2) 1.01779(5) 0.0418(3) Uani 1 1 d . . . . .
O2 O 0.21593(11) -0.2921(3) 0.60688(7) 0.0714(5) Uani 1 1 d . . . . .
O3 O 0.15128(11) 0.0357(4) 0.64080(7) 0.0735(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.385(3) . ?
C1 C6 1.390(3) . ?
C1 N1 1.428(2) . ?
C2 C3 1.369(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.413(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.455(3) . ?
C7 C8 1.334(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.456(3) . ?
C8 H8 0.9300 . ?
C9 C14 1.391(2) . ?
C9 C10 1.403(3) . ?
C10 C11 1.372(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(2) . ?
C13 H13 0.9300 . ?
C14 N1 1.4367(19) . ?
C15 O1 1.2395(19) . ?
C15 N2 1.339(2) . ?
C15 N1 1.367(2) . ?
C16 C17 1.376(3) . ?
C16 C21 1.388(3) . ?
C16 C22 1.473(3) . ?
C17 C18 1.383(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.385(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.294(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.493(3) . ?
C23 H23 0.9300 . ?
C24 O3 1.226(3) . ?
C24 O2 1.288(3) . ?
N2 H2A 0.85(2) . ?
N2 H2B 0.85(2) . ?
O2 H2C 1.06(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 C1 C6 121.97(17) . . ?
C2 C1 N1 119.00(16) . . ?
C6 C1 N1 119.02(16) . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 121.3(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 116.2(2) . . ?
C1 C6 C7 122.42(17) . . ?
C5 C6 C7 121.3(2) . . ?
C8 C7 C6 127.77(19) . . ?
C8 C7 H7 116.1 . . ?
C6 C7 H7 116.1 . . ?
C7 C8 C9 126.9(2) . . ?
C7 C8 H8 116.6 . . ?
C9 C8 H8 116.6 . . ?
C14 C9 C10 116.92(18) . . ?
C14 C9 C8 122.32(16) . . ?
C10 C9 C8 120.66(18) . . ?
C11 C10 C9 121.2(2) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.57(17) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 119.5(2) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 119.89(18) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 121.73(15) . . ?
C13 C14 N1 119.60(15) . . ?
C9 C14 N1 118.66(15) . . ?
O1 C15 N2 121.16(15) . . ?
O1 C15 N1 121.47(13) . . ?
N2 C15 N1 117.36(14) . . ?
C17 C16 C21 117.98(17) . . ?
C17 C16 C22 118.39(18) . . ?
C21 C16 C22 123.62(18) . . ?
C16 C17 C18 121.11(19) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 119.65(18) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C21 119.8(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C16 121.09(19) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
C23 C22 C16 127.6(2) . . ?
C23 C22 H22 116.2 . . ?
C16 C22 H22 116.2 . . ?
C22 C23 C24 123.2(2) . . ?
C22 C23 H23 118.4 . . ?
C24 C23 H23 118.4 . . ?
O3 C24 O2 125.45(18) . . ?
O3 C24 C23 122.8(2) . . ?
O2 C24 C23 111.78(19) . . ?
C15 N1 C1 122.03(12) . . ?
C15 N1 C14 119.61(13) . . ?
C1 N1 C14 115.51(12) . . ?
C15 N2 H2A 115.4(14) . . ?
C15 N2 H2B 122.3(14) . . ?
H2A N2 H2B 122(2) . . ?
C24 O2 H2C 114.2(18) . . ?

_refine_diff_density_max         0.486
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.056



####################################################################### 
# 
# 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_cbz_va_acn
_database_code_depnum_ccdc_archive 'CCDC 2225590'
loop_
_audit_author_name
_audit_author_address
'Ranjit Thakuria'
;Gauhati University
India
;
_audit_update_record             
;
2023-02-17 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT919_cbz_va_acn          
;
PROBLEM: Reflection # Likely Affected by the Beamstop ...          1 Check
RESPONSE: The B-Alert for CBZ-VA cocrystal beamstop alert maybe due to instrumental setup as X-ray source was relatively new and the detector is at a relatively longer distance compared to recommended in order to minimize the chance of detector damage.
;
_vrf_PLAT934_cbz_va_acn          
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          3 Check
RESPONSE: Due to poor crystal quality and room temperature data.
;
# Added during the CSD deposition process: Friday 17 February 2023 04:07 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 N2 O6'
_chemical_formula_weight         422.42

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   8.4203(4)
_cell_length_b                   21.4155(8)
_cell_length_c                   11.6437(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.670(2)
_cell_angle_gamma                90
_cell_volume                     2075.66(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6891
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      26.31

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17655
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.625
_diffrn_reflns_theta_max         26.429
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4257
_reflns_number_gt                3487
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0598P)²+0.4045P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0228(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4257
_refine_ls_number_parameters     306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1177
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.003

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.88286(16) 0.01850(6) 0.29519(11) 0.0338(3) Uani 1 1 d . . . . .
C2 C 0.8656(2) -0.04539(7) 0.30585(14) 0.0461(4) Uani 1 1 d . . . . .
H2 H 0.905801 -0.072378 0.254673 0.055 Uiso 1 1 calc R U . . .
C3 C 0.7882(2) -0.06877(9) 0.39297(17) 0.0594(5) Uani 1 1 d . . . . .
H3 H 0.776281 -0.111676 0.400601 0.071 Uiso 1 1 calc R U . . .
C4 C 0.7283(2) -0.02869(10) 0.46882(15) 0.0625(5) Uani 1 1 d . . . . .
H4 H 0.674257 -0.044585 0.526412 0.075 Uiso 1 1 calc R U . . .
C5 C 0.7484(2) 0.03438(9) 0.45938(14) 0.0542(4) Uani 1 1 d . . . . .
H5 H 0.708061 0.060940 0.511206 0.065 Uiso 1 1 calc R U . . .
C6 C 0.82854(17) 0.05977(7) 0.37325(12) 0.0379(3) Uani 1 1 d . . . . .
C7 C 0.85374(19) 0.12736(7) 0.36914(14) 0.0443(4) Uani 1 1 d . . . . .
H7 H 0.775314 0.152133 0.394652 0.053 Uiso 1 1 calc R U . . .
C8 C 0.97556(18) 0.15763(7) 0.33325(14) 0.0427(4) Uani 1 1 d . . . . .
H8 H 0.970853 0.201004 0.334475 0.051 Uiso 1 1 calc R U . . .
C9 C 1.11548(17) 0.13028(6) 0.29224(11) 0.0345(3) Uani 1 1 d . . . . .
C10 C 1.26432(19) 0.15994(7) 0.31621(13) 0.0431(4) Uani 1 1 d . . . . .
H10 H 1.271163 0.198648 0.352844 0.052 Uiso 1 1 calc R U . . .
C11 C 1.40107(19) 0.13319(8) 0.28686(14) 0.0498(4) Uani 1 1 d . . . . .
H11 H 1.499116 0.153663 0.304584 0.060 Uiso 1 1 calc R U . . .
C12 C 1.39369(19) 0.07619(9) 0.23128(15) 0.0517(4) Uani 1 1 d . . . . .
H12 H 1.486548 0.058107 0.211967 0.062 Uiso 1 1 calc R U . . .
C13 C 1.24744(18) 0.04600(8) 0.20435(13) 0.0437(4) Uani 1 1 d . . . . .
H13 H 1.241716 0.007585 0.166698 0.052 Uiso 1 1 calc R U . . .
C14 C 1.10980(16) 0.07310(6) 0.23357(11) 0.0326(3) Uani 1 1 d . . . . .
C15 C 0.86537(17) 0.05288(6) 0.09565(11) 0.0318(3) Uani 1 1 d . . . . .
C16 C 0.70744(17) 0.19942(6) 0.63471(12) 0.0353(3) Uani 1 1 d . . . . .
C17 C 0.85867(17) 0.22427(6) 0.62685(12) 0.0361(3) Uani 1 1 d . . . . .
H17 H 0.948959 0.209405 0.674968 0.043 Uiso 1 1 calc R U . . .
C18 C 0.87393(17) 0.27085(6) 0.54771(13) 0.0380(3) Uani 1 1 d . . . . .
C19 C 0.73699(19) 0.29358(7) 0.47646(15) 0.0449(4) Uani 1 1 d . . . . .
C20 C 0.58893(18) 0.26743(7) 0.48171(14) 0.0459(4) Uani 1 1 d . . . . .
H20 H 0.499065 0.281394 0.432008 0.055 Uiso 1 1 calc R U . . .
C21 C 0.57357(18) 0.22052(7) 0.56059(13) 0.0402(3) Uani 1 1 d . . . . .
H21 H 0.473329 0.203025 0.564073 0.048 Uiso 1 1 calc R U . . .
C22 C 0.69181(18) 0.15243(7) 0.72503(13) 0.0417(3) Uani 1 1 d . . . . .
C23 C 1.1588(2) 0.27798(10) 0.59489(19) 0.0648(5) Uani 1 1 d . . . . .
H23A H 1.155953 0.283890 0.676275 0.097 Uiso 1 1 calc R U . . .
H23B H 1.246923 0.301171 0.572669 0.097 Uiso 1 1 calc R U . . .
H23C H 1.172537 0.234417 0.579560 0.097 Uiso 1 1 calc R U . . .
H1A H 1.032(3) 0.0958(8) 0.0308(16) 0.055(5) Uiso 1 1 d . . . . .
H3A H 0.532(3) 0.1056(12) 0.782(2) 0.095(8) Uiso 1 1 d . . . . .
H5A H 0.841(4) 0.3566(12) 0.414(2) 0.105(9) Uiso 1 1 d . . . . .
H6A H 0.565(3) 0.0573(10) 0.957(2) 0.077(7) Uiso 1 1 d . . . . .
H1B H 0.874(3) 0.0931(9) -0.0511(19) 0.065(6) Uiso 1 1 d . . . . .
H6B H 0.411(3) 0.0379(10) 0.896(2) 0.079(7) Uiso 1 1 d . . . . .
N1 N 0.93611(19) 0.08258(7) 0.01587(12) 0.0467(3) Uani 1 1 d . . . . .
N2 N 0.95658(13) 0.04314(5) 0.20139(9) 0.0326(3) Uani 1 1 d . . . . .
O1 O 0.72416(12) 0.03445(5) 0.07519(9) 0.0428(3) Uani 1 1 d . . . . .
O2 O 0.80055(15) 0.13704(7) 0.79899(11) 0.0692(4) Uani 1 1 d . . . . .
O3 O 0.54734(16) 0.12855(7) 0.71707(13) 0.0742(5) Uani 1 1 d . . . . .
O4 O 1.01380(13) 0.29917(5) 0.53059(11) 0.0561(3) Uani 1 1 d . . . . .
O5 O 0.74609(18) 0.34089(7) 0.40100(15) 0.0788(5) Uani 1 1 d . . . . .
O6 O 0.47924(14) 0.06767(5) 0.90042(10) 0.0427(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.384(2) . ?
C1 C6 1.393(2) . ?
C1 N2 1.4357(17) . ?
C2 C3 1.380(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.465(2) . ?
C7 C8 1.333(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.459(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.395(2) . ?
C9 C14 1.3996(19) . ?
C10 C11 1.375(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(2) . ?
C13 H13 0.9300 . ?
C14 N2 1.4389(17) . ?
C15 O1 1.2413(17) . ?
C15 N1 1.3376(19) . ?
C15 N2 1.3653(17) . ?
C16 C21 1.388(2) . ?
C16 C17 1.396(2) . ?
C16 C22 1.476(2) . ?
C17 C18 1.377(2) . ?
C17 H17 0.9300 . ?
C18 O4 1.3659(18) . ?
C18 C19 1.402(2) . ?
C19 O5 1.3507(19) . ?
C19 C20 1.376(2) . ?
C20 C21 1.380(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 O2 1.2046(18) . ?
C22 O3 1.3100(19) . ?
C23 O4 1.408(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N1 H1A 0.85(2) . ?
N1 H1B 0.90(2) . ?
O3 H3A 0.93(3) . ?
O5 H5A 0.86(3) . ?
O6 H6A 0.93(2) . ?
O6 H6B 0.86(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.29(14) . . ?
C2 C1 N2 119.68(13) . . ?
C6 C1 N2 119.02(12) . . ?
C3 C2 C1 119.52(17) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.21(16) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.08(16) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.32(17) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 117.51(14) . . ?
C1 C6 C7 122.82(13) . . ?
C5 C6 C7 119.66(15) . . ?
C8 C7 C6 127.80(14) . . ?
C8 C7 H7 116.1 . . ?
C6 C7 H7 116.1 . . ?
C7 C8 C9 127.24(13) . . ?
C7 C8 H8 116.4 . . ?
C9 C8 H8 116.4 . . ?
C10 C9 C14 117.36(13) . . ?
C10 C9 C8 119.81(13) . . ?
C14 C9 C8 122.76(12) . . ?
C11 C10 C9 121.42(14) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 120.37(14) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 119.70(15) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 119.86(14) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 121.24(13) . . ?
C13 C14 N2 120.02(12) . . ?
C9 C14 N2 118.72(12) . . ?
O1 C15 N1 122.13(13) . . ?
O1 C15 N2 121.12(12) . . ?
N1 C15 N2 116.74(13) . . ?
C21 C16 C17 119.90(13) . . ?
C21 C16 C22 120.92(13) . . ?
C17 C16 C22 119.14(12) . . ?
C18 C17 C16 119.88(13) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
O4 C18 C17 126.07(13) . . ?
O4 C18 C19 114.19(13) . . ?
C17 C18 C19 119.74(13) . . ?
O5 C19 C20 118.33(14) . . ?
O5 C19 C18 121.54(14) . . ?
C20 C19 C18 120.13(13) . . ?
C19 C20 C21 120.13(14) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 120.13(14) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
O2 C22 O3 122.78(15) . . ?
O2 C22 C16 123.80(14) . . ?
O3 C22 C16 113.42(13) . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 N1 H1A 121.8(13) . . ?
C15 N1 H1B 117.4(13) . . ?
H1A N1 H1B 120.2(18) . . ?
C15 N2 C1 119.55(11) . . ?
C15 N2 C14 121.81(11) . . ?
C1 N2 C14 116.06(10) . . ?
C22 O3 H3A 113.1(15) . . ?
C18 O4 C23 118.50(13) . . ?
C19 O5 H5A 108.7(18) . . ?
H6A O6 H6B 108(2) . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.051



####################################################################### 
# 
# 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_cbz_34dhba
_database_code_depnum_ccdc_archive 'CCDC 2225591'
loop_
_audit_author_name
_audit_author_address
'Ranjit Thakuria'
;Gauhati University
India
;
_audit_update_record             
;
2022-12-10 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
_audit_creation_date             2022-01-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'Carbamazapine-34dihydroxybenzoic acid hydrate cocrystal'
_chemical_formula_moiety         'C15 H12 N2 O, 0.25(C7 H5 O4), 0.5(H2 O)'
_chemical_formula_sum            'C16.75 H14.25 N2 O2.50'
_chemical_formula_weight         283.55
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   21.0388(2)
_cell_length_b                   5.22610(10)
_cell_length_c                   26.3430(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.1200(10)
_cell_angle_gamma                90
_cell_volume                     2831.87(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13349
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.275
_cell_measurement_theta_min      3.432
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_correction_T_min  0.779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Xcalibur
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1190
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0104
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13349
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.275
_diffrn_reflns_theta_min         3.432
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  Xcalibur
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2384
_reflns_number_total             2582
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.00098(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         2582
_refine_ls_number_restraints     153
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²+1.9001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1132
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 C006-C00F = C00F-C00J = C00J-C00E = C00E-C00A = C00A-C007 = C007-C006
 1.39 with sigma of 0.01
 C5-C8 = C8-C1 = C1-C4 = C4-C3 = C3-C10 = C10-C5
 1.39 with sigma of 0.01
 C009-C00D = C00D-C00H = C00H-C00I = C00I-C00G = C00G-C008 = C008-C009
 1.39 with sigma of 0.01
 C10-O7 \\sim O7-C4
 with sigma of 0.001
 C5-C1 \\sim C8-C4 \\sim C1-C3 \\sim C4-C10 \\sim C3-C5 \\sim C10-C8
 with sigma of 0.02
 C006-C00J \\sim C00F-C00E \\sim C00J-C00A \\sim C00E-C007 \\sim C00A-C006
\\sim C007-C00F
 with sigma of 0.02
 C009-C00H \\sim C00D-C00I \\sim C00H-C00G \\sim C00I-C008 \\sim C00G-C009
\\sim C008-C00D
 with sigma of 0.02
 C3-O2 \\sim O2-C1
 with sigma of 0.001
3. Restrained planarity
 C006, C00F, C00J, C00E, C00A, C007
 with sigma of 0.1
 C5, C8, C1, C4, C3, C10
 with sigma of 0.1
 C009, C00D, C00H, C00I, C00G, C008
 with sigma of 0.1
4. Rigid bond restraints
 C4, O2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Rigid body (RIGU) restrains
 C5, C2, O1, O8, C10, C8, C3, H10, C1, H8, C4, O7, H1, O2, H7, H2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Fixed Sof: C2(0.25) O1(0.25) C4(0.25) C5(0.25) O8(0.25) C3(0.25) C1(0.25)
 H1(0.25) O7(0.25) H7(0.25) C10(0.25) H10(0.25) C8(0.25) H8(0.25) O2(0.25)
 H2(0.25) O3(0.5) H3A(0.5) H3B(0.5)
7.a Free rotating group:
 O3(H3A,H3B)
7.b Aromatic/amide H refined with riding coordinates:
 C00A(H00C), C00B(H00D), C00C(H00E), C00D(H00F), C00E(H00G), C00F(H00H),
 C00G(H00I), C00H(H00J), C00I(H00K), C00J(H00L), C1(H1), C10(H10), C8(H8)
7.c X=CH2 refined with riding coordinates:
 N003(H00A,H00B)
7.d Idealised tetrahedral OH refined as rotating group:
 O7(H7), O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O001 O 0.44118(6) 0.1700(3) 0.44801(5) 0.0785(4) Uani 1 1 d . . . . .
N002 N 0.49223(6) 0.4117(3) 0.39725(5) 0.0526(3) Uani 1 1 d . . . . .
N003 N 0.54951(7) 0.2230(3) 0.47243(5) 0.0667(4) Uani 1 1 d . . . . .
H00A H 0.551577 0.130385 0.499705 0.080 Uiso 1 1 calc R U . . .
H00B H 0.584266 0.290149 0.465928 0.080 Uiso 1 1 calc R U . . .
C005 C 0.49206(8) 0.2629(3) 0.44002(6) 0.0547(4) Uani 1 1 d . . . . .
C006 C 0.43270(7) 0.4501(3) 0.35984(6) 0.0525(4) Uani 1 1 d D . . . .
C007 C 0.41952(8) 0.3005(3) 0.31557(6) 0.0540(4) Uani 1 1 d D . . . .
C008 C 0.57124(8) 0.3273(4) 0.34375(6) 0.0600(5) Uani 1 1 d D . . . .
C009 C 0.55148(7) 0.4750(3) 0.38143(6) 0.0528(4) Uani 1 1 d D . . . .
C00A C 0.35924(9) 0.3344(4) 0.28187(7) 0.0695(5) Uani 1 1 d D . . . .
H00C H 0.348483 0.232206 0.252419 0.083 Uiso 1 1 calc R U . . .
C00B C 0.46591(10) 0.1178(4) 0.30263(7) 0.0711(5) Uani 1 1 d . . . . .
H00D H 0.448231 -0.024777 0.283664 0.085 Uiso 1 1 calc R U . . .
C00C C 0.53087(10) 0.1300(4) 0.31472(7) 0.0744(6) Uani 1 1 d . . . . .
H00E H 0.552805 -0.004985 0.303031 0.089 Uiso 1 1 calc R U . . .
C00D C 0.58928(8) 0.6734(4) 0.40562(9) 0.0756(6) Uani 1 1 d D . . . .
H00F H 0.574483 0.774210 0.429840 0.091 Uiso 1 1 calc R U . . .
C00E C 0.31570(9) 0.5135(4) 0.29103(9) 0.0781(6) Uani 1 1 d D . . . .
H00G H 0.275849 0.531726 0.268064 0.094 Uiso 1 1 calc R U . . .
C00F C 0.38942(8) 0.6348(4) 0.36847(10) 0.0834(7) Uani 1 1 d D . . . .
H00H H 0.399860 0.738748 0.397694 0.100 Uiso 1 1 calc R U . . .
C00G C 0.63289(10) 0.3801(6) 0.33397(8) 0.0888(8) Uani 1 1 d D . . . .
H00I H 0.648167 0.281246 0.309715 0.107 Uiso 1 1 calc R U . . .
C00H C 0.64921(9) 0.7225(5) 0.39391(11) 0.0948(8) Uani 1 1 d D . . . .
H00J H 0.674424 0.857927 0.409852 0.114 Uiso 1 1 calc R U . . .
C00I C 0.67127(10) 0.5720(6) 0.35892(11) 0.1016(10) Uani 1 1 d D . . . .
H00K H 0.712308 0.600041 0.352072 0.122 Uiso 1 1 calc R U . . .
C00J C 0.33095(9) 0.6665(4) 0.33420(11) 0.0947(8) Uani 1 1 d D . . . .
H00L H 0.301856 0.791086 0.340251 0.114 Uiso 1 1 calc R U . . .
C2 C 0.7455(12) 1.2762(17) 0.5055(10) 0.047(2) Uani 0.25 1 d . . P A -1
O1 O 0.7887(6) 1.4095(19) 0.4924(5) 0.069(2) Uani 0.25 1 d . . P A -1
C4 C 0.7523(11) 0.4627(10) 0.5008(12) 0.0507(14) Uani 0.25 1 d D U P A -1
C5 C 0.7454(12) 0.9932(9) 0.5037(12) 0.0437(18) Uani 0.25 1 d D . P A -1
O8 O 0.6983(6) 1.3739(17) 0.5231(5) 0.064(2) Uani 0.25 1 d . . P A -1
C3 C 0.7056(10) 0.5809(15) 0.5233(10) 0.051(4) Uani 0.25 1 d D . P A -1
C1 C 0.7942(9) 0.6085(14) 0.4787(8) 0.045(3) Uani 0.25 1 d D . P A -1
H1 H 0.824527 0.528937 0.462918 0.054 Uiso 0.25 1 calc R U P A -1
O7 O 0.6660(2) 0.4532(8) 0.5387(2) 0.0567(11) Uani 0.25 1 d D . P A -1
H7 H 0.637768 0.546516 0.545827 0.085 Uiso 0.25 1 calc R U P A -1
C10 C 0.7030(11) 0.8461(13) 0.5252(11) 0.049(3) Uani 0.25 1 d D . P A -1
H10 H 0.672553 0.925360 0.540939 0.059 Uiso 0.25 1 calc R U P A -1
C8 C 0.7911(10) 0.8764(13) 0.4802(9) 0.044(2) Uani 0.25 1 d D . P A -1
H8 H 0.819293 0.975003 0.465475 0.053 Uiso 0.25 1 calc R U P A -1
O2 O 0.7548(13) 0.2015(9) 0.4991(14) 0.065(2) Uani 0.25 1 d D U P A -1
H2 H 0.725817 0.141231 0.511940 0.098 Uiso 0.25 1 calc R U P A -1
O3 O 0.68702(14) 0.8648(5) 0.55189(16) 0.0777(9) Uani 0.5 1 d G . P B -2
H3A H 0.646732 0.853693 0.551957 0.117 Uiso 0.5 1 d G U P B -2
H3B H 0.695732 0.726884 0.537646 0.117 Uiso 0.5 1 d G U P B -2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C005 1.2332(19) . ?
N002 C005 1.369(2) . ?
N002 C006 1.436(2) . ?
N002 C009 1.4336(18) . ?
N003 H00A 0.8600 . ?
N003 H00B 0.8600 . ?
N003 C005 1.342(2) . ?
C006 C007 1.383(2) . ?
C006 C00F 1.378(2) . ?
C007 C00A 1.398(2) . ?
C007 C00B 1.456(2) . ?
C008 C009 1.388(2) . ?
C008 C00C 1.448(3) . ?
C008 C00G 1.402(3) . ?
C009 C00D 1.378(2) . ?
C00A H00C 0.9300 . ?
C00A C00E 1.366(3) . ?
C00B H00D 0.9300 . ?
C00B C00C 1.338(3) . ?
C00C H00E 0.9300 . ?
C00D H00F 0.9300 . ?
C00D C00H 1.384(3) . ?
C00E H00G 0.9300 . ?
C00E C00J 1.372(3) . ?
C00F H00H 0.9300 . ?
C00F C00J 1.375(3) . ?
C00G H00I 0.9300 . ?
C00G C00I 1.366(4) . ?
C00H H00J 0.9300 . ?
C00H C00I 1.365(4) . ?
C00I H00K 0.9300 . ?
C00J H00L 0.9300 . ?
C2 O1 1.250(15) . ?
C2 C5 1.480(9) . ?
C2 O8 1.286(18) . ?
C4 C3 1.394(8) . ?
C4 C1 1.382(7) . ?
C4 O2 1.367(7) . ?
C5 C10 1.386(7) . ?
C5 C8 1.389(7) . ?
C3 O7 1.204(13) . ?
C3 C10 1.388(8) . ?
C1 H1 0.9300 . ?
C1 C8 1.402(8) . ?
O7 H7 0.8200 . ?
C10 H10 0.9300 . ?
C8 H8 0.9300 . ?
O2 H2 0.8200 . ?
O3 H3A 0.8500 . ?
O3 H3B 0.8502 . ?

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
C005 N002 C006 119.43(13) . . ?
C005 N002 C009 121.53(13) . . ?
C009 N002 C006 117.04(13) . . ?
H00A N003 H00B 120.0 . . ?
C005 N003 H00A 120.0 . . ?
C005 N003 H00B 120.0 . . ?
O001 C005 N002 121.08(15) . . ?
O001 C005 N003 121.91(16) . . ?
N003 C005 N002 117.01(14) . . ?
C007 C006 N002 119.42(14) . . ?
C00F C006 N002 119.74(16) . . ?
C00F C006 C007 120.84(16) . . ?
C006 C007 C00A 117.28(16) . . ?
C006 C007 C00B 122.87(15) . . ?
C00A C007 C00B 119.84(16) . . ?
C009 C008 C00C 122.90(15) . . ?
C009 C008 C00G 116.71(19) . . ?
C00G C008 C00C 120.39(18) . . ?
C008 C009 N002 119.24(15) . . ?
C00D C009 N002 119.45(15) . . ?
C00D C009 C008 121.23(16) . . ?
C007 C00A H00C 119.1 . . ?
C00E C00A C007 121.82(19) . . ?
C00E C00A H00C 119.1 . . ?
C007 C00B H00D 116.1 . . ?
C00C C00B C007 127.89(19) . . ?
C00C C00B H00D 116.1 . . ?
C008 C00C H00E 116.0 . . ?
C00B C00C C008 128.03(17) . . ?
C00B C00C H00E 116.0 . . ?
C009 C00D H00F 120.0 . . ?
C009 C00D C00H 120.0(2) . . ?
C00H C00D H00F 120.0 . . ?
C00A C00E H00G 120.1 . . ?
C00A C00E C00J 119.79(18) . . ?
C00J C00E H00G 120.1 . . ?
C006 C00F H00H 119.8 . . ?
C00J C00F C006 120.5(2) . . ?
C00J C00F H00H 119.8 . . ?
C008 C00G H00I 118.9 . . ?
C00I C00G C008 122.2(2) . . ?
C00I C00G H00I 118.9 . . ?
C00D C00H H00J 120.0 . . ?
C00I C00H C00D 119.9(2) . . ?
C00I C00H H00J 120.0 . . ?
C00G C00I H00K 120.1 . . ?
C00H C00I C00G 119.82(19) . . ?
C00H C00I H00K 120.1 . . ?
C00E C00J C00F 119.70(19) . . ?
C00E C00J H00L 120.1 . . ?
C00F C00J H00L 120.1 . . ?
O1 C2 C5 122.9(14) . . ?
O1 C2 O8 122.7(9) . . ?
O8 C2 C5 114.4(12) . . ?
C1 C4 C3 120.2(4) . . ?
O2 C4 C3 119.4(5) . . ?
O2 C4 C1 120.3(6) . . ?
C10 C5 C2 122.6(9) . . ?
C10 C5 C8 120.2(4) . . ?
C8 C5 C2 117.2(9) . . ?
O7 C3 C4 119.9(6) . . ?
O7 C3 C10 120.4(6) . . ?
C10 C3 C4 119.7(7) . . ?
C4 C1 H1 120.0 . . ?
C4 C1 C8 120.1(7) . . ?
C8 C1 H1 120.0 . . ?
C3 O7 H7 109.5 . . ?
C5 C10 C3 120.3(8) . . ?
C5 C10 H10 119.8 . . ?
C3 C10 H10 119.8 . . ?
C5 C8 C1 119.5(7) . . ?
C5 C8 H8 120.3 . . ?
C1 C8 H8 120.3 . . ?
C4 O2 H2 109.5 . . ?
H3A O3 H3B 104.5 . . ?

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
N002 C006 C007 C00A 176.22(15) . . . . ?
N002 C006 C007 C00B -5.2(2) . . . . ?
N002 C006 C00F C00J -177.14(19) . . . . ?
N002 C009 C00D C00H 174.45(17) . . . . ?
C005 N002 C006 C007 -97.35(18) . . . . ?
C005 N002 C006 C00F 82.6(2) . . . . ?
C005 N002 C009 C008 95.41(18) . . . . ?
C005 N002 C009 C00D -81.5(2) . . . . ?
C006 N002 C005 O001 -3.0(2) . . . . ?
C006 N002 C005 N003 176.85(14) . . . . ?
C006 N002 C009 C008 -68.40(19) . . . . ?
C006 N002 C009 C00D 114.69(17) . . . . ?
C006 C007 C00A C00E 2.2(3) . . . . ?
C006 C007 C00B C00C -29.9(3) . . . . ?
C006 C00F C00J C00E -0.2(4) . . . . ?
C007 C006 C00F C00J 2.8(3) . . . . ?
C007 C00A C00E C00J 0.3(3) . . . . ?
C007 C00B C00C C008 0.2(3) . . . . ?
C008 C009 C00D C00H -2.4(3) . . . . ?
C008 C00G C00I C00H -1.3(3) . . . . ?
C009 N002 C005 O001 -166.41(16) . . . . ?
C009 N002 C005 N003 13.4(2) . . . . ?
C009 N002 C006 C007 66.8(2) . . . . ?
C009 N002 C006 C00F -113.26(19) . . . . ?
C009 C008 C00C C00B 28.3(3) . . . . ?
C009 C008 C00G C00I -1.9(3) . . . . ?
C009 C00D C00H C00I -1.0(3) . . . . ?
C00A C007 C00B C00C 148.6(2) . . . . ?
C00A C00E C00J C00F -1.3(3) . . . . ?
C00B C007 C00A C00E -176.36(18) . . . . ?
C00C C008 C009 N002 7.9(2) . . . . ?
C00C C008 C009 C00D -175.28(17) . . . . ?
C00C C008 C00G C00I 177.11(19) . . . . ?
C00D C00H C00I C00G 2.7(3) . . . . ?
C00F C006 C007 C00A -3.7(3) . . . . ?
C00F C006 C007 C00B 174.82(18) . . . . ?
C00G C008 C009 N002 -173.11(15) . . . . ?
C00G C008 C009 C00D 3.7(2) . . . . ?
C00G C008 C00C C00B -150.6(2) . . . . ?
C2 C5 C10 C3 -179(3) . . . . ?
C2 C5 C8 C1 178(3) . . . . ?
O1 C2 C5 C10 170.4(17) . . . . ?
O1 C2 C5 C8 -9(3) . . . . ?
C4 C3 C10 C5 2(2) . . . . ?
C4 C1 C8 C5 0(2) . . . . ?
O8 C2 C5 C10 -8(3) . . . . ?
O8 C2 C5 C8 173.5(15) . . . . ?
C3 C4 C1 C8 2(4) . . . . ?
C1 C4 C3 O7 174.1(18) . . . . ?
C1 C4 C3 C10 -2(4) . . . . ?
O7 C3 C10 C5 -175(2) . . . . ?
C10 C5 C8 C1 -0.6(17) . . . . ?
C8 C5 C10 C3 0(2) . . . . ?
O2 C4 C3 O7 -4(4) . . . . ?
O2 C4 C3 C10 180(3) . . . . ?
O2 C4 C1 C8 179(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_cbz_35dhba
_database_code_depnum_ccdc_archive 'CCDC 2225592'
loop_
_audit_author_name
_audit_author_address
'Ranjit Thakuria'
;Gauhati University
India
;
_audit_update_record             
;
2022-12-10 deposited with the CCDC.	2023-03-06 downloaded from the CCDC.
;
_audit_creation_date             2022-05-10
_audit_creation_method           
;
Olex2 1.5-dev
(compiled 2022.05.04 svn.r4f934e98 for OlexSys, GUI svn.r6264)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'Carbamazapine-35dihydroxybenzoic acid hydrate cocrystal'
_chemical_formula_moiety         '0.5(C15 H12 N2 O), 0.1(C7 H3 O4), 0.4(H2 O)'
_chemical_formula_sum            'C8.20 H7.10 N O1.30'
_chemical_formula_weight         140.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   21.29468(18)
_cell_length_b                   5.12107(5)
_cell_length_c                   26.6635(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.5459(9)
_cell_angle_gamma                90
_cell_volume                     2826.81(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    13629
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.127
_cell_measurement_theta_min      3.410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Olex2
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1179
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0094
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            13629
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.127
_diffrn_reflns_theta_min         3.410
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  Xcalibur
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2359
_reflns_number_total             2561
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.00119(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         2561
_refine_ls_number_restraints     168
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0633P)²+1.5303P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1324
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 C1-C10 = C10-C12 = C12-C11 = C11-C6 = C6-C4 = C4-C1
 1.39 with sigma of 0.01
 O3-C17
 1.3 with sigma of 0.001
 C3-C7 = C7-C13 = C13-C15 = C15-C14 = C14-C5 = C5-C3
 1.39 with sigma of 0.01
 O20-C17
 1.3 with sigma of 0.001
 O20-O3
 2.3 with sigma of 0.02
 C19-C20 = C20-C16 = C16-C18
 1.39 with sigma of 0.01
 C18-C17
 1.45 with sigma of 0.001
 O20-C17 \\sim O3-C17
 with sigma of 0.01
 O20-C18 \\sim C18-O3
 with sigma of 0.01
 C1-C12 \\sim C10-C11 \\sim C12-C6 \\sim C11-C4 \\sim C6-C1 \\sim C4-C10
 with sigma of 0.02
 C3-C13 \\sim C7-C15 \\sim C13-C14 \\sim C15-C5 \\sim C14-C3 \\sim C5-C7
 with sigma of 0.02
 C19-C16 \\sim C20-C18
 with sigma of 0.02
 C16-O2 \\sim O2-C19
 with sigma of 0.001
 C16-C17 \\sim C17-C1A
 with sigma of 0.001
3. Restrained planarity
 C18, C16, C17, C20, O3, O20, O2, C19
 with sigma of 0.01
 C18, C19, C20, C16
 with sigma of 0.1
 C1, C10, C12, C11, C6, C4
 with sigma of 0.1
 C3, C7, C13, C15, C14, C5
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C17) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O20) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
5. Rigid body (RIGU) restrains
 C18, C16, C17, C20, O3, O20, O2, C19
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C18, C16, C17, C1A, H16, C20, O3, O20, C1B, O2, C19, O4
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Fixed Sof: C18(0.2) C16(0.2) H16(0.2) C20(0.2) O2(0.2) C19(0.2) H19(0.2)
 C17(0.2) O3(0.2) O20(0.2) O5(0.6) H5A(0.6) H5B(0.6) C1A(0.2) H1A(0.2) C1B(0.2)
 O4(0.2) O8(0.2) H8A(0.2) H8B(0.2)
7.a Riding coordinates:
 O5(H5A,H5B), O8(H8A,H8B)
7.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C19(H19), C1A(H1A)
7.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.55713(6) 0.8247(3) 0.55312(5) 0.0819(5) Uani 1 1 d . . . . .
N N 0.50564(6) 0.5924(3) 0.60362(5) 0.0516(3) Uani 1 1 d . . . . .
N2 N 0.44932(7) 0.7766(3) 0.52705(5) 0.0667(4) Uani 1 1 d . . . . .
H2A H 0.447774 0.865966 0.499485 0.080 Uiso 1 1 calc R U . . .
H2B H 0.414445 0.712997 0.533101 0.080 Uiso 1 1 calc R U . . .
C1 C 0.56493(7) 0.5525(3) 0.64137(6) 0.0517(4) Uani 1 1 d D . . . .
C2 C 0.50594(8) 0.7364(3) 0.56050(6) 0.0557(4) Uani 1 1 d . . . . .
C3 C 0.44655(7) 0.5299(3) 0.61809(6) 0.0534(4) Uani 1 1 d D . . . .
C4 C 0.57884(8) 0.7049(3) 0.68565(6) 0.0554(4) Uani 1 1 d D . . . .
C5 C 0.42787(8) 0.6789(4) 0.65578(6) 0.0625(5) Uani 1 1 d D . . . .
C6 C 0.63942(9) 0.6706(4) 0.71951(7) 0.0705(5) Uani 1 1 d D . . . .
H6 H 0.650613 0.773620 0.748983 0.085 Uiso 1 1 calc R U . . .
C7 C 0.40800(8) 0.3308(4) 0.59282(8) 0.0685(5) Uani 1 1 d D . . . .
H7 H 0.421913 0.229503 0.568564 0.082 Uiso 1 1 calc R U . . .
C8 C 0.46875(10) 0.8800(4) 0.68557(7) 0.0753(6) Uani 1 1 d . . . . .
H8 H 0.447281 1.017224 0.697171 0.090 Uiso 1 1 calc R U . . .
C9 C 0.53325(10) 0.8917(4) 0.69828(7) 0.0707(5) Uani 1 1 d . . . . .
H9 H 0.551178 1.036283 0.717478 0.085 Uiso 1 1 calc R U . . .
C10 C 0.60791(8) 0.3655(4) 0.63255(9) 0.0730(6) Uani 1 1 d D . . . .
H10 H 0.597100 0.260897 0.603287 0.088 Uiso 1 1 calc R U . . .
C11 C 0.68256(9) 0.4887(4) 0.71022(9) 0.0768(6) Uani 1 1 d D . . . .
H11 H 0.722567 0.470252 0.733164 0.092 Uiso 1 1 calc R U . . .
C12 C 0.66673(9) 0.3336(4) 0.66697(10) 0.0836(7) Uani 1 1 d D . . . .
H12 H 0.695588 0.207648 0.660994 0.100 Uiso 1 1 calc R U . . .
C13 C 0.34855(9) 0.2824(5) 0.60369(10) 0.0867(7) Uani 1 1 d D . . . .
H13 H 0.322721 0.147206 0.587002 0.104 Uiso 1 1 calc R U . . .
C14 C 0.36681(10) 0.6259(6) 0.66467(8) 0.0893(8) Uani 1 1 d D . . . .
H14 H 0.352355 0.725342 0.688904 0.107 Uiso 1 1 calc R U . . .
C15 C 0.32785(10) 0.4335(6) 0.63899(10) 0.0978(9) Uani 1 1 d D . . . .
H15 H 0.287337 0.405074 0.645455 0.117 Uiso 1 1 calc R U . . .
C18 C 0.7522(4) 1.0024(9) 0.5060(3) 0.0440(13) Uani 0.2 1 d D . P A -1
C16 C 0.7058(5) 0.8546(13) 0.5234(3) 0.045(3) Uani 0.2 1 d D . P A -1
H16 H 0.674495 0.939206 0.536591 0.054 Uiso 0.2 1 calc R U P A -1
C20 C 0.7063(5) 0.5858(17) 0.5212(4) 0.0400(18) Uani 0.2 1 d D . P A -1
O2 O 0.6631(6) 0.448(2) 0.5378(5) 0.058(2) Uani 0.2 1 d D . P A -1
C19 C 0.7532(5) 0.4597(13) 0.5018(6) 0.0542(13) Uani 0.2 1 d D U P A -1
H19 H 0.758670 0.279750 0.504936 0.065 Uiso 0.2 1 calc R U P A -1
C17 C 0.7500(3) 1.2849(9) 0.50893(18) 0.0516(12) Uani 0.2 1 d D U P A -1
O3 O 0.7940(4) 1.4161(14) 0.4930(3) 0.0575(15) Uani 0.2 1 d D U P A -1
O20 O 0.7040(4) 1.3800(18) 0.5281(3) 0.0560(18) Uani 0.2 1 d D U P A -1
O5 O 0.68420(10) 0.8657(5) 0.56343(12) 0.0893(8) Uani 0.6 1 d . . P A 1
H5A H 0.646577 0.828787 0.567015 0.134 Uiso 0.6 1 d R U P A 1
H5B H 0.682397 1.027467 0.556045 0.134 Uiso 0.6 1 d R U P A 1
C1A C 0.7932(7) 0.883(2) 0.4788(5) 0.062(4) Uani 0.2 1 d D . P A -1
H1A H 0.819483 0.982371 0.462719 0.074 Uiso 0.2 1 calc R U P A -1
C1B C 0.7934(8) 0.615(3) 0.4766(7) 0.073(4) Uani 0.2 1 d . . P A -1
O4 O 0.8328(9) 0.461(3) 0.4539(6) 0.091(4) Uani 0.2 1 d . . P A -1
O8 O 0.6922(4) 1.3530(17) 0.5179(4) 0.051(2) Uiso 0.2 1 d . . P A 1
H8A H 0.716789 1.367028 0.497164 0.077 Uiso 0.2 1 d R U P A 1
H8B H 0.700999 1.485608 0.537484 0.077 Uiso 0.2 1 d R U P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2378(19) . ?
N C1 1.433(2) . ?
N C2 1.367(2) . ?
N C3 1.4358(18) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C2 1.337(2) . ?
C1 C4 1.388(2) . ?
C1 C10 1.382(2) . ?
C3 C5 1.392(2) . ?
C3 C7 1.382(3) . ?
C4 C6 1.402(2) . ?
C4 C9 1.458(2) . ?
C5 C8 1.458(3) . ?
C5 C14 1.402(3) . ?
C6 H6 0.9300 . ?
C6 C11 1.371(3) . ?
C7 H7 0.9300 . ?
C7 C13 1.386(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.337(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C12 1.378(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C15 1.369(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.365(4) . ?
C15 H15 0.9300 . ?
C18 C16 1.408(8) . ?
C18 C17 1.4504(11) . ?
C18 C1A 1.400(11) . ?
C16 H16 0.9300 . ?
C16 C20 1.378(9) . ?
C16 O5 1.258(11) . ?
C20 O2 1.315(17) . ?
C20 C19 1.388(9) . ?
C19 H19 0.9300 . ?
C19 C1B 1.445(17) . ?
C17 O3 1.3004(11) . ?
C17 O20 1.3005(11) . ?
C17 O8 1.355(11) . ?
O5 H5A 0.8500 . ?
O5 H5B 0.8501 . ?
C1A H1A 0.9300 . ?
C1A C1B 1.374(18) . ?
C1B O4 1.39(2) . ?
O8 H8A 0.8501 . ?
O8 H8B 0.8500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N C3 117.58(12) . . ?
C2 N C1 119.38(13) . . ?
C2 N C3 121.54(13) . . ?
H2A N2 H2B 120.0 . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
C4 C1 N 119.63(14) . . ?
C10 C1 N 119.28(15) . . ?
C10 C1 C4 121.08(16) . . ?
O1 C2 N 120.57(16) . . ?
O1 C2 N2 121.86(15) . . ?
N2 C2 N 117.57(14) . . ?
C5 C3 N 119.23(16) . . ?
C7 C3 N 119.44(15) . . ?
C7 C3 C5 121.26(16) . . ?
C1 C4 C6 117.28(15) . . ?
C1 C4 C9 122.99(15) . . ?
C6 C4 C9 119.71(16) . . ?
C3 C5 C8 123.05(15) . . ?
C3 C5 C14 116.7(2) . . ?
C14 C5 C8 120.25(18) . . ?
C4 C6 H6 119.2 . . ?
C11 C6 C4 121.54(19) . . ?
C11 C6 H6 119.2 . . ?
C3 C7 H7 120.1 . . ?
C3 C7 C13 119.9(2) . . ?
C13 C7 H7 120.1 . . ?
C5 C8 H8 116.0 . . ?
C9 C8 C5 128.07(17) . . ?
C9 C8 H8 116.0 . . ?
C4 C9 H9 116.1 . . ?
C8 C9 C4 127.78(19) . . ?
C8 C9 H9 116.1 . . ?
C1 C10 H10 119.9 . . ?
C12 C10 C1 120.24(19) . . ?
C12 C10 H10 119.9 . . ?
C6 C11 H11 120.0 . . ?
C6 C11 C12 120.06(18) . . ?
C12 C11 H11 120.0 . . ?
C10 C12 H12 120.1 . . ?
C11 C12 C10 119.72(18) . . ?
C11 C12 H12 120.1 . . ?
C7 C13 H13 120.0 . . ?
C15 C13 C7 120.0(2) . . ?
C15 C13 H13 120.0 . . ?
C5 C14 H14 118.9 . . ?
C15 C14 C5 122.3(2) . . ?
C15 C14 H14 118.9 . . ?
C13 C15 H15 120.1 . . ?
C14 C15 C13 119.83(19) . . ?
C14 C15 H15 120.1 . . ?
C16 C18 C17 119.0(6) . . ?
C1A C18 C16 120.6(5) . . ?
C1A C18 C17 119.6(7) . . ?
C18 C16 H16 119.7 . . ?
C20 C16 C18 120.7(9) . . ?
C20 C16 H16 119.7 . . ?
O5 C16 C18 132.8(5) . . ?
O5 C16 H16 38.9 . . ?
O5 C16 C20 95.1(5) . . ?
C16 C20 C19 119.6(9) . . ?
O2 C20 C16 120.6(7) . . ?
O2 C20 C19 119.8(6) . . ?
C20 C19 H19 120.9 . . ?
C20 C19 C1B 118.3(6) . . ?
C1B C19 H19 120.9 . . ?
O3 C17 C18 117.6(5) . . ?
O3 C17 O20 126.9(6) . . ?
O3 C17 O8 132.7(7) . . ?
O20 C17 C18 115.5(5) . . ?
O20 C17 O8 15.0(6) . . ?
O8 C17 C18 107.9(7) . . ?
C16 O5 H5A 128.8 . . ?
C16 O5 H5B 81.6 . . ?
H5A O5 H5B 104.5 . . ?
C18 C1A H1A 121.1 . . ?
C1B C1A C18 117.7(13) . . ?
C1B C1A H1A 121.1 . . ?
C1A C1B C19 121.6(12) . . ?
C1A C1B O4 126.4(14) . . ?
O4 C1B C19 111.9(13) . . ?
C17 O8 H8A 35.0 . . ?
C17 O8 H8B 103.6 . . ?
H8A O8 H8B 104.5 . . ?

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
N C1 C4 C6 -175.58(14) . . . . ?
N C1 C4 C9 5.5(2) . . . . ?
N C1 C10 C12 176.48(17) . . . . ?
N C3 C5 C8 -6.7(2) . . . . ?
N C3 C5 C14 173.82(14) . . . . ?
N C3 C7 C13 -174.99(16) . . . . ?
C1 N C2 O1 2.3(2) . . . . ?
C1 N C2 N2 -177.81(14) . . . . ?
C1 N C3 C5 67.09(19) . . . . ?
C1 N C3 C7 -115.70(17) . . . . ?
C1 C4 C6 C11 -1.9(3) . . . . ?
C1 C4 C9 C8 29.6(3) . . . . ?
C1 C10 C12 C11 0.0(3) . . . . ?
C2 N C1 C4 99.69(17) . . . . ?
C2 N C1 C10 -79.1(2) . . . . ?
C2 N C3 C5 -98.87(18) . . . . ?
C2 N C3 C7 78.3(2) . . . . ?
C3 N C1 C4 -66.58(19) . . . . ?
C3 N C1 C10 114.58(17) . . . . ?
C3 N C2 O1 168.04(16) . . . . ?
C3 N C2 N2 -12.1(2) . . . . ?
C3 C5 C8 C9 -28.6(3) . . . . ?
C3 C5 C14 C15 1.8(3) . . . . ?
C3 C7 C13 C15 0.7(3) . . . . ?
C4 C1 C10 C12 -2.3(3) . . . . ?
C4 C6 C11 C12 -0.4(3) . . . . ?
C5 C3 C7 C13 2.2(3) . . . . ?
C5 C8 C9 C4 -0.3(3) . . . . ?
C5 C14 C15 C13 0.9(3) . . . . ?
C6 C4 C9 C8 -149.3(2) . . . . ?
C6 C11 C12 C10 1.3(3) . . . . ?
C7 C3 C5 C8 176.16(16) . . . . ?
C7 C3 C5 C14 -3.3(2) . . . . ?
C7 C13 C15 C14 -2.2(3) . . . . ?
C8 C5 C14 C15 -177.69(19) . . . . ?
C9 C4 C6 C11 177.06(18) . . . . ?
C10 C1 C4 C6 3.2(2) . . . . ?
C10 C1 C4 C9 -175.69(17) . . . . ?
C14 C5 C8 C9 150.8(2) . . . . ?
C18 C16 C20 O2 179.6(4) . . . . ?
C18 C16 C20 C19 0.3(6) . . . . ?
C18 C1A C1B C19 -0.6(18) . . . . ?
C18 C1A C1B O4 -176.4(12) . . . . ?
C16 C18 C17 O3 179.4(3) . . . . ?
C16 C18 C17 O20 0.2(3) . . . . ?
C16 C18 C17 O8 -13.8(7) . . . . ?
C16 C18 C1A C1B -9.7(14) . . . . ?
C16 C20 C19 C1B -10.3(13) . . . . ?
C20 C19 C1B C1A 10.6(19) . . . . ?
C20 C19 C1B O4 -173.0(11) . . . . ?
O2 C20 C19 C1B 170.4(9) . . . . ?
C17 C18 C16 C20 179.9(3) . . . . ?
C17 C18 C16 O5 -46.3(9) . . . . ?
C17 C18 C1A C1B -179.4(9) . . . . ?
O5 C16 C20 O2 31.7(8) . . . . ?
O5 C16 C20 C19 -147.6(7) . . . . ?
C1A C18 C16 C20 10.2(9) . . . . ?
C1A C18 C16 O5 144.0(9) . . . . ?
C1A C18 C17 O3 -10.8(8) . . . . ?
C1A C18 C17 O20 170.0(8) . . . . ?
C1A C18 C17 O8 156.0(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
