# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_D19288
_database_code_depnum_ccdc_archive 'CCDC 2063017'
loop_
_audit_author_name
_audit_author_address
'Jonathan Becker'
;Justus Liebig University Giessen
Germany
;
_audit_update_record             
;
2021-02-15 deposited with the CCDC.	2021-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'Nordiamantane carboxylic acid'
_chemical_name_common            14
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28

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'
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                   6.5170(4)
_cell_length_b                   10.4112(7)
_cell_length_c                   15.8832(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.934(2)
_cell_angle_gamma                90
_cell_volume                     1067.36(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      37.06

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7124
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker PHOTON100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            77056
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.346
_diffrn_reflns_theta_max         30.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3129
_reflns_number_gt                2631
_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       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker D8 Venture Dual I\mS fixed chi instrument. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0547P)²+0.6060P] 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_number_reflns         3129
_refine_ls_number_parameters     148
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
O1 O 0.42006(13) 0.50111(8) 0.59288(5) 0.01669(18) Uani 1 1 d . . . . .
O2 O 0.64349(14) 0.63918(9) 0.54670(5) 0.0196(2) Uani 1 1 d D . . . .
H2 H 0.616(3) 0.5916(16) 0.5008(10) 0.029 Uiso 1 1 d D U . . .
C1 C 0.53560(17) 0.59481(11) 0.60475(7) 0.0125(2) Uani 1 1 d . . . . .
C2 C 0.55856(17) 0.67105(10) 0.68571(6) 0.0117(2) Uani 1 1 d . . . . .
C3 C 0.53514(16) 0.58905(10) 0.76821(6) 0.0115(2) Uani 1 1 d . . . . .
H3 H 0.516724 0.495162 0.756189 0.014 Uiso 1 1 calc R U . . .
C4 C 0.34737(17) 0.65023(11) 0.80293(7) 0.0133(2) Uani 1 1 d . . . . .
H4 H 0.216197 0.615735 0.770778 0.016 Uiso 1 1 calc R U . . .
C5 C 0.37527(17) 0.79110(11) 0.77763(7) 0.0141(2) Uani 1 1 d . . . . .
H5 H 0.255642 0.845825 0.788563 0.017 Uiso 1 1 calc R U . . .
C6 C 0.38510(17) 0.77472(11) 0.68243(7) 0.0147(2) Uani 1 1 d . . . . .
H6A H 0.425030 0.855535 0.656142 0.018 Uiso 1 1 calc R U . . .
H6AB H 0.252012 0.743488 0.651643 0.018 Uiso 1 1 calc R U . . .
C7 C 0.76455(17) 0.74445(11) 0.70755(7) 0.0131(2) Uani 1 1 d . . . . .
H7A H 0.883752 0.693643 0.693583 0.016 Uiso 1 1 calc R U . . .
H7AB H 0.761238 0.828493 0.678233 0.016 Uiso 1 1 calc R U . . .
C8 C 0.76980(17) 0.76021(11) 0.80376(7) 0.0125(2) Uani 1 1 d . . . . .
H8 H 0.905462 0.794993 0.831552 0.015 Uiso 1 1 calc R U . . .
C9 C 0.73662(16) 0.61999(11) 0.82919(7) 0.0124(2) Uani 1 1 d . . . . .
H9 H 0.852524 0.565891 0.813668 0.015 Uiso 1 1 calc R U . . .
C10 C 0.58336(17) 0.83971(11) 0.82672(7) 0.0141(2) Uani 1 1 d . . . . .
H10 H 0.603028 0.931988 0.812295 0.017 Uiso 1 1 calc R U . . .
C11 C 0.57488(18) 0.82761(12) 0.92299(7) 0.0163(2) Uani 1 1 d . . . . .
H11A H 0.459180 0.880183 0.938502 0.020 Uiso 1 1 calc R U . . .
H11B H 0.705396 0.860601 0.954961 0.020 Uiso 1 1 calc R U . . .
C12 C 0.54399(18) 0.68618(12) 0.94751(7) 0.0155(2) Uani 1 1 d . . . . .
H12 H 0.538536 0.679787 1.009980 0.019 Uiso 1 1 calc R U . . .
C13 C 0.34261(18) 0.63365(12) 0.89823(7) 0.0163(2) Uani 1 1 d . . . . .
H13A H 0.327629 0.541549 0.911634 0.020 Uiso 1 1 calc R U . . .
H13B H 0.222554 0.680445 0.915172 0.020 Uiso 1 1 calc R U . . .
C14 C 0.72268(18) 0.60420(11) 0.92396(7) 0.0151(2) Uani 1 1 d . . . . .
H14A H 0.854444 0.631532 0.957819 0.018 Uiso 1 1 calc R U . . .
H14B H 0.698829 0.512807 0.936826 0.018 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2309(14) . ?
O2 C1 1.3180(13) . ?
O2 H2 0.879(14) . ?
C1 C2 1.5009(15) . ?
C2 C7 1.5421(15) . ?
C2 C6 1.5586(15) . ?
C2 C3 1.5888(14) . ?
C3 C4 1.5472(15) . ?
C3 C9 1.5540(15) . ?
C3 H3 1.0000 . ?
C4 C13 1.5280(15) . ?
C4 C5 1.5381(16) . ?
C4 H4 1.0000 . ?
C5 C6 1.5316(15) . ?
C5 C10 1.5529(16) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.5325(14) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C9 1.5379(15) . ?
C8 C10 1.5546(15) . ?
C8 H8 1.0000 . ?
C9 C14 1.5293(14) . ?
C9 H9 1.0000 . ?
C10 C11 1.5428(15) . ?
C10 H10 1.0000 . ?
C11 C12 1.5434(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C14 1.5313(16) . ?
C12 C13 1.5332(16) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 H2 108.3(12) . . ?
O1 C1 O2 123.01(10) . . ?
O1 C1 C2 122.47(10) . . ?
O2 C1 C2 114.48(10) . . ?
C1 C2 C7 115.82(9) . . ?
C1 C2 C6 110.58(9) . . ?
C7 C2 C6 105.61(9) . . ?
C1 C2 C3 114.39(9) . . ?
C7 C2 C3 105.10(8) . . ?
C6 C2 C3 104.35(8) . . ?
C4 C3 C9 109.53(8) . . ?
C4 C3 C2 104.10(8) . . ?
C9 C3 C2 103.51(8) . . ?
C4 C3 H3 113.0 . . ?
C9 C3 H3 113.0 . . ?
C2 C3 H3 113.0 . . ?
C13 C4 C5 112.70(9) . . ?
C13 C4 C3 115.58(9) . . ?
C5 C4 C3 99.88(8) . . ?
C13 C4 H4 109.4 . . ?
C5 C4 H4 109.4 . . ?
C3 C4 H4 109.4 . . ?
C6 C5 C4 100.04(9) . . ?
C6 C5 C10 112.29(9) . . ?
C4 C5 C10 107.83(9) . . ?
C6 C5 H5 112.0 . . ?
C4 C5 H5 112.0 . . ?
C10 C5 H5 112.0 . . ?
C5 C6 C2 99.97(8) . . ?
C5 C6 H6A 111.8 . . ?
C2 C6 H6A 111.8 . . ?
C5 C6 H6AB 111.8 . . ?
C2 C6 H6AB 111.8 . . ?
H6A C6 H6AB 109.5 . . ?
C8 C7 C2 100.15(8) . . ?
C8 C7 H7A 111.7 . . ?
C2 C7 H7A 111.7 . . ?
C8 C7 H7AB 111.7 . . ?
C2 C7 H7AB 111.7 . . ?
H7A C7 H7AB 109.5 . . ?
C7 C8 C9 100.12(8) . . ?
C7 C8 C10 112.35(9) . . ?
C9 C8 C10 107.52(9) . . ?
C7 C8 H8 112.1 . . ?
C9 C8 H8 112.1 . . ?
C10 C8 H8 112.1 . . ?
C14 C9 C8 112.97(9) . . ?
C14 C9 C3 115.55(9) . . ?
C8 C9 C3 99.81(8) . . ?
C14 C9 H9 109.4 . . ?
C8 C9 H9 109.4 . . ?
C3 C9 H9 109.4 . . ?
C11 C10 C5 108.83(9) . . ?
C11 C10 C8 108.97(9) . . ?
C5 C10 C8 111.43(9) . . ?
C11 C10 H10 109.2 . . ?
C5 C10 H10 109.2 . . ?
C8 C10 H10 109.2 . . ?
C10 C11 C12 110.59(9) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C14 C12 C13 107.62(9) . . ?
C14 C12 C11 109.88(9) . . ?
C13 C12 C11 110.11(10) . . ?
C14 C12 H12 109.7 . . ?
C13 C12 H12 109.7 . . ?
C11 C12 H12 109.7 . . ?
C4 C13 C12 109.42(9) . . ?
C4 C13 H13A 109.8 . . ?
C12 C13 H13A 109.8 . . ?
C4 C13 H13B 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C9 C14 C12 109.33(9) . . ?
C9 C14 H14A 109.8 . . ?
C12 C14 H14A 109.8 . . ?
C9 C14 H14B 109.8 . . ?
C12 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?

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
O2 H2 O1 0.879(14) 1.762(14) 2.6394(12) 175.4(17) 3_666 yes

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.060

