data_publication_text
_publ_contact_author_name        'Jeffrey R. Long'
_publ_contact_author_address     
;Department of Chemistry
University of California, Berkeley
USA
;
_publ_contact_author_email       jrlong@berkeley.edu
_publ_contact_author_phone       510-642-0860
loop_
_publ_author_name
_publ_author_address

'Siegelman, Rebecca L.'
;Department of Chemistry 
University of California, Berkeley
USA
;
'Milner, Phillip J.'
;Department of Chemistry
University of California, Berkeley
USA
;
'Forse, Alexander C.'
;Department of Chemistry
University of California, Berkeley
USA
;
'Lee, Jung-Hoon'
;Department of Chemistry
University of California, Berkeley
USA
;
'Colwell, Kristen A.'
;Department of Chemistry
University of California, Berkeley
USA
; 
'Neaton, Jeffrey B.'
;Department of Chemistry
University of California, Berkeley
USA
; 
'Reimer, Jeffrey A.'
;Department of Chemistry
University of California, Berkeley
USA
;
'Weston, Simon C.'
;ExxonMobil Research and Engineering Company
Annandale, NJ
USA
;
'Long, Jeffrey R.'
;Department of Chemistry
University of California, Berkeley
USA
;
data_pjm029s
_audit_creation_date               2019-01-12
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2016/6'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_acknowledgements
;
This research used resources of the Advanced
Light Source, which is a DOE Office of Science
User Facility under contract no. DE-AC02-05CH11231.
; 
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              2-ampd-CO2
_chemical_name_systematic          ?
_chemical_formula_moiety           'C7 H14 N2 O2'
_chemical_formula_sum              'C7 H14 N2 O2'
_chemical_formula_weight           158.20
_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' 0.0040 0.0020 'ANOMDisVal Program in PLATON Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13'
 'H' 'H' 0.0000 0.0000 'ANOMDisVal Program in PLATON Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13'
 'N' 'N' 0.0080 0.0040 'ANOMDisVal Program in PLATON Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13'
 'O' 'O' 0.0130 0.0070 'ANOMDisVal Program in PLATON Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13'

_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             14
_space_group_name_H-M_alt          'P 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
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                     5.0969(3)
_cell_length_b                     18.5652(11)
_cell_length_c                     8.4393(5)
_cell_angle_alpha                  90
_cell_angle_beta                   102.214(4)
_cell_angle_gamma                  90
_cell_volume                       780.49(8)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      3614
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        24.517
_cell_measurement_theta_min        2.250
_shelx_estimated_absorpt_T_max     0.999
_shelx_estimated_absorpt_T_min     0.989
_exptl_absorpt_coefficient_mu      0.104
_exptl_absorpt_correction_T_max    0.999
_exptl_absorpt_correction_T_min    0.825
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1369 before and 0.0623 after correction.
The Ratio of minimum to maximum transmission is 0.8256.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.346
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      'not measured'
_exptl_crystal_description         plate
_exptl_crystal_F_000               344
_exptl_crystal_preparation         ?
_exptl_crystal_size_max            0.107
_exptl_crystal_size_mid            0.04
_exptl_crystal_size_min            0.014
_exptl_special_details
;
X-ray diffraction analyses were performed on single crystals coated with
 Paratone-N oil and mounted on MiTeGen loops. Crystals were frozen at a
 temperature of 100 K by an Oxford Cryosystems Cyrostream using N2 during
 the experiments. Data was collected at Beamline 12.2.1 at the Advanced
 Light Source, Lawrence Berkeley National Laboratory using synchrotron
 radiation (lamda = 0.7288 angstrom) and a Bruker D8 Diffractometer with 
 a Bruker PHOTON II CMOS detector.
;
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0596
_diffrn_reflns_av_unetI/netI       0.0338
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.998
_diffrn_reflns_limit_h_max         5
_diffrn_reflns_limit_h_min         -5
_diffrn_reflns_limit_k_max         21
_diffrn_reflns_limit_k_min         -21
_diffrn_reflns_limit_l_max         9
_diffrn_reflns_limit_l_min         -9
_diffrn_reflns_number              9923
_diffrn_reflns_point_group_measured_fraction_full  0.998
_diffrn_reflns_point_group_measured_fraction_max  0.998
_diffrn_reflns_theta_full          24.547
_diffrn_reflns_theta_max           24.547
_diffrn_reflns_theta_min           2.250
_diffrn_ambient_temperature        100(2)
_diffrn_detector_area_resol_mean   7.39
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.998
_diffrn_measurement_device_type    'Bruker D8 with PHOTON II detector'
_diffrn_measurement_method         'φ and ω shutterless scans'
_diffrn_radiation_monochromator    'silicon 111'
_diffrn_radiation_type             synchrotron
_diffrn_radiation_wavelength       0.7288
_diffrn_source
;
Advanced Light Source, station 12.2.1
;
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  974
_reflns_number_total               1208
_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         'SAINT V8.38A (Bruker-AXS, Madison WI, 2016)'
_computing_data_collection         'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction          'SAINT V8.38A (Bruker-AXS, Madison WI, 2016)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.266
_refine_diff_density_min           -0.277
_refine_diff_density_rms           0.062
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.127
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       109
_refine_ls_number_reflns           1208
_refine_ls_number_restraints       3
_refine_ls_R_factor_all            0.0643
_refine_ls_R_factor_gt             0.0522
_refine_ls_restrained_S_all        1.128
_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)+(0.0611P)²+0.5882P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1291
_refine_ls_wR_factor_ref           0.1362
_refine_special_details            
;
Thermal parameters were refined anisotropically for all non-hydrogen atoms. 
All hydrogen atoms bound to carbon atoms were placed in ideal positions and 
refined using a riding model. Semi-free refinement was used for hydrogen atoms 
bound to the carbamate nitrogen (N1) and ammonium nitrogen (N2) atoms. These 
hydrogen atoms (H1 and H2A, H2B) were located in the difference map, and the 
corresponding N-H distances were restrained to ideal values (DFIX).
;
_vrf_THETM01_pjm029s
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: This compound crystallized as very thin plates that diffracted 
poorly. Several synthetic and experimental parameters were varied to achieve 
the best possible diffraction in this dataset.  
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2. Restrained distances
 N2-H2A = N2-H2B
 0.91 with sigma of 0.02
 N1-H1
 0.88 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2C,H2D), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     diffmap
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 0.2849(4) 0.87921(9) 0.5473(2) 0.0363(5) Uani 1 1 d . . . . .
 O2 O 0.6308(3) 0.81975(11) 0.6960(3) 0.0443(6) Uani 1 1 d . . . . .
 N1 N 0.2176(4) 0.80610(11) 0.7473(2) 0.0230(5) Uani 1 1 d D . . . .
 H1 H 0.039(4) 0.8173(13) 0.718(3) 0.028 Uiso 1 1 d DR . . . .
 N2 N 0.2578(5) 0.61771(12) 0.9033(3) 0.0329(6) Uani 1 1 d D . . . .
 H2A H 0.440(4) 0.6185(15) 0.955(3) 0.040 Uiso 1 1 d DR . . . .
 H2B H 0.170(5) 0.6308(15) 0.982(3) 0.040 Uiso 1 1 d DR . . . .
 C1 C 0.3855(5) 0.83582(13) 0.6607(3) 0.0280(6) Uani 1 1 d . . . . .
 C2 C 0.2920(5) 0.74658(13) 0.8565(3) 0.0289(6) Uani 1 1 d . . . . .
 H2C H 0.203939 0.752106 0.949706 0.035 Uiso 1 1 calc R . . . .
 H2D H 0.488593 0.747499 0.898777 0.035 Uiso 1 1 calc R . . . .
 C3 C 0.2134(5) 0.67420(13) 0.7756(3) 0.0242(6) Uani 1 1 d . . . . .
 H3 H 0.017370 0.675624 0.725196 0.029 Uiso 1 1 calc R . . . .
 C4 C 0.3629(5) 0.65393(13) 0.6465(3) 0.0255(6) Uani 1 1 d . . . . .
 H4A H 0.558190 0.654607 0.693159 0.031 Uiso 1 1 calc R . . . .
 H4B H 0.325621 0.690045 0.558253 0.031 Uiso 1 1 calc R . . . .
 C5 C 0.2835(6) 0.57987(15) 0.5768(3) 0.0399(7) Uani 1 1 d . . . . .
 H5A H 0.392596 0.567339 0.496591 0.048 Uiso 1 1 calc R . . . .
 H5B H 0.092272 0.580189 0.520396 0.048 Uiso 1 1 calc R . . . .
 C6 C 0.3270(5) 0.52379(13) 0.7115(3) 0.0305(6) Uani 1 1 d . . . . .
 H6A H 0.261867 0.476340 0.665983 0.037 Uiso 1 1 calc R . . . .
 H6B H 0.521193 0.519492 0.759334 0.037 Uiso 1 1 calc R . . . .
 C7 C 0.1800(5) 0.54463(14) 0.8410(4) 0.0388(7) Uani 1 1 d . . . . .
 H7A H -0.015758 0.543223 0.796110 0.047 Uiso 1 1 calc R . . . .
 H7B H 0.221291 0.509555 0.931184 0.047 Uiso 1 1 calc R . . . .


_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 1.273(3) . ?
 O2 C1 1.259(3) . ?
 N1 H1 0.913(17) . ?
 N1 C1 1.354(3) . ?
 N1 C2 1.438(3) . ?
 N2 H2A 0.939(18) . ?
 N2 H2B 0.912(18) . ?
 N2 C3 1.486(3) . ?
 N2 C7 1.478(4) . ?
 C2 H2C 0.9900 . ?
 C2 H2D 0.9900 . ?
 C2 C3 1.522(3) . ?
 C3 H3 1.0000 . ?
 C3 C4 1.504(3) . ?
 C4 H4A 0.9900 . ?
 C4 H4B 0.9900 . ?
 C4 C5 1.516(4) . ?
 C5 H5A 0.9900 . ?
 C5 H5B 0.9900 . ?
 C5 C6 1.523(4) . ?
 C6 H6A 0.9900 . ?
 C6 H6B 0.9900 . ?
 C6 C7 1.500(4) . ?
 C7 H7A 0.9900 . ?
 C7 H7B 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 N1 H1 117.8(16) . . ?
 C1 N1 C2 123.2(2) . . ?
 C2 N1 H1 117.5(16) . . ?
 H2A N2 H2B 105(3) . . ?
 C3 N2 H2A 107.9(18) . . ?
 C3 N2 H2B 108.6(18) . . ?
 C7 N2 H2A 110.0(18) . . ?
 C7 N2 H2B 111.6(19) . . ?
 C7 N2 C3 113.7(2) . . ?
 O1 C1 N1 117.6(2) . . ?
 O2 C1 O1 123.3(2) . . ?
 O2 C1 N1 119.0(3) . . ?
 N1 C2 H2C 109.1 . . ?
 N1 C2 H2D 109.1 . . ?
 N1 C2 C3 112.5(2) . . ?
 H2C C2 H2D 107.8 . . ?
 C3 C2 H2C 109.1 . . ?
 C3 C2 H2D 109.1 . . ?
 N2 C3 C2 108.2(2) . . ?
 N2 C3 H3 108.2 . . ?
 N2 C3 C4 109.02(19) . . ?
 C2 C3 H3 108.2 . . ?
 C4 C3 C2 114.9(2) . . ?
 C4 C3 H3 108.2 . . ?
 C3 C4 H4A 109.2 . . ?
 C3 C4 H4B 109.2 . . ?
 C3 C4 C5 111.9(2) . . ?
 H4A C4 H4B 107.9 . . ?
 C5 C4 H4A 109.2 . . ?
 C5 C4 H4B 109.2 . . ?
 C4 C5 H5A 109.6 . . ?
 C4 C5 H5B 109.6 . . ?
 C4 C5 C6 110.2(2) . . ?
 H5A C5 H5B 108.1 . . ?
 C6 C5 H5A 109.6 . . ?
 C6 C5 H5B 109.6 . . ?
 C5 C6 H6A 109.5 . . ?
 C5 C6 H6B 109.5 . . ?
 H6A C6 H6B 108.1 . . ?
 C7 C6 C5 110.6(2) . . ?
 C7 C6 H6A 109.5 . . ?
 C7 C6 H6B 109.5 . . ?
 N2 C7 C6 111.0(2) . . ?
 N2 C7 H7A 109.4 . . ?
 N2 C7 H7B 109.4 . . ?
 C6 C7 H7A 109.4 . . ?
 C6 C7 H7B 109.4 . . ?
 H7A C7 H7B 108.0 . . ?

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
 N1 H1 O2 0.913(17) 2.052(18) 2.941(3) 164(2) 1_455
 N2 H2A O1 0.939(18) 1.766(18) 2.705(3) 179(3) 4_676
 N2 H2B O1 0.912(18) 2.15(2) 2.920(3) 141(2) 4_576
 N2 H2B O2 0.912(18) 2.07(2) 2.923(3) 155(3) 4_576

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
 N1 C2 C3 N2 -170.95(19) . . . . ?
 N1 C2 C3 C4 67.0(3) . . . . ?
 N2 C3 C4 C5 55.8(3) . . . . ?
 C1 N1 C2 C3 -93.3(3) . . . . ?
 C2 N1 C1 O1 167.7(2) . . . . ?
 C2 N1 C1 O2 -12.6(3) . . . . ?
 C2 C3 C4 C5 177.4(2) . . . . ?
 C3 N2 C7 C6 56.9(3) . . . . ?
 C3 C4 C5 C6 -56.3(3) . . . . ?
 C4 C5 C6 C7 55.0(3) . . . . ?
 C5 C6 C7 N2 -55.0(3) . . . . ?
 C7 N2 C3 C2 178.1(2) . . . . ?
 C7 N2 C3 C4 -56.4(3) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'




